##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_2a
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
(3Z)-3-(1H-pyrrol-2-ylmethylidene)-1H-indol-
2(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H10 N2 O'
_chemical_formula_sum     'C13 H10 N2 O'
_chemical_formula_iupac     'C13 H10 N2 O'
_chemical_formula_weight     210.23
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P bca'
_symmetry_space_group_name_Hall     '-P (2a)c (2a)b'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y-1/2, z-1/2'
_cell_length_a     14.6031(6)
_cell_length_b     6.2725(3)
_cell_length_c     22.6997(12)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2079.25(17)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     23500
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.01
_exptl_crystal_density_diffrn     1.343
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     880
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min     0.9759
_exptl_absorpt_correction_T_max     0.9991
_exptl_special_details
;
SADABS was used to perform the Absorption correction. Estimated minimum
and maximum transmission from SADABS: 0.6100 and 0.7456. The given Tmin
and Tmax were generated using the SHELX SIZE command.
NMR spectra were measured on a Jeol EX270 spectrometer at 270 MHz (¹H) and 68
MHz (¹³C) in CDCl₃. High-resolution mass spectra were performed by the
EPSRC facility, Swansea University, Wales. ¹H NMR (270 MHz, CDCl₃, δ,
p.p.m.): 13.26 (1H, s), 7.68 (1H, s), 7.47 (2H, dd, J = 6.24 Hz, J =  7.70 Hz),
7.20--7.03 (3H, m), 6.89 (1H, d, J = 7.70 Hz), 6.78 (1H, m), 6.39 (1H, m).
¹³C NMR (75 MHz, CDCl₃, δ, p.p.m.): 169.6, 137.7, 130.0, 126.8, 126.7,
125.6, 125.4, 121.9, 120.6, 118.1, 116.3, 111.7, 109.4.
IR (KBr, ν, cm⁻¹): 3034, 1672,1349, 1040, 740.
HRMS: m/z calculated for C₁₃H₁₁N₂O (MH+) 211.0866; found
211.0868.
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type
                                'Bruker Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     15759
_diffrn_reflns_av_R_equivalents     0.0853
_diffrn_reflns_av_sigmaI/netI     0.0573
_diffrn_reflns_theta_min     3.32
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     27
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     1828
_reflns_number_gt     1412
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0817
_refine_ls_R_factor_gt     0.0530
_refine_ls_wR_factor_gt     0.0998
_refine_ls_wR_factor_ref     0.1104
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_restrained_S_all     1.053
_refine_ls_number_reflns     1828
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0367P)²+1.4244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.177
_refine_diff_density_min     -0.221
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Version 2.01; Farrugia, 1997) and
Mercury (Version 1.4.2; Macrae et al., 2006)
;
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.42080(14) 0.2332(3) 0.46443(9) 0.0211(5) Uani d . 1 . .
    C C2 0.37404(13) 0.4387(3) 0.45202(9) 0.0191(5) Uani d . 1 . .
    C C3 0.36448(13) 0.5425(3) 0.50957(9) 0.0186(5) Uani d . 1 . .
    C C4 0.40375(13) 0.4076(3) 0.55179(9) 0.0188(5) Uani d . 1 . .
    C C5 0.40700(13) 0.4582(3) 0.61097(9) 0.0221(5) Uani d . 1 . .
    H H5 0.4347 0.3653 0.6388 0.027 Uiso calc R 1 . .
    C C6 0.36794(14) 0.6511(4) 0.62817(10) 0.0255(5) Uani d . 1 . .
    H H6 0.3683 0.6899 0.6686 0.031 Uiso calc R 1 . .
    C C7 0.32856(14) 0.7878(4) 0.58724(9) 0.0247(5) Uani d . 1 . .
    H H7 0.3023 0.9184 0.6001 0.030 Uiso calc R 1 . .
    C C8 0.32708(13) 0.7356(3) 0.52748(9) 0.0219(5) Uani d . 1 . .
    H H8 0.3009 0.8305 0.4995 0.026 Uiso calc R 1 . .
    C C9 0.34741(13) 0.5206(3) 0.39925(9) 0.0209(5) Uani d . 1 . .
    H H9 0.3161 0.6530 0.4020 0.025 Uiso calc R 1 . .
    C C10 0.35810(13) 0.4434(3) 0.34065(9) 0.0228(5) Uani d . 1 . .
    C C11 0.33119(15) 0.5405(4) 0.28777(10) 0.0281(5) Uani d . 1 . .
    H H11 0.2998 0.6725 0.2841 0.034 Uiso calc R 1 . .
    C C12 0.35874(16) 0.4083(4) 0.24160(10) 0.0315(6) Uani d . 1 . .
    H H12 0.3496 0.4342 0.2008 0.038 Uiso calc R 1 . .
    C C13 0.40153(15) 0.2338(4) 0.26588(9) 0.0299(6) Uani d . 1 . .
    H H13 0.4273 0.1179 0.2446 0.036 Uiso calc R 1 . .
    N N1 0.43597(11) 0.2248(3) 0.52342(7) 0.0204(4) Uani d . 1 . .
    H H1 0.4628 0.1176 0.5415 0.025 Uiso calc R 1 . .
    N N2 0.40075(12) 0.2551(3) 0.32536(7) 0.0257(5) Uani d . 1 . .
    H H2 0.4240 0.1627 0.3504 0.031 Uiso calc R 1 . .
    O O1 0.44323(9) 0.0872(2) 0.42984(6) 0.0249(4) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.250(2) ?
    C1 N1 . 1.358(3) ?
    C1 C2 . 1.486(3) ?
    C2 C9 . 1.360(3) ?
    C2 C3 . 1.467(3) ?
    C3 C8 . 1.389(3) ?
    C3 C4 . 1.401(3) ?
    C4 C5 . 1.381(3) ?
    C4 N1 . 1.396(3) ?
    C5 C6 . 1.394(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.389(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.396(3) ?
    C7 H7 . 0.9500 ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.424(3) ?
    C9 H9 . 0.9500 ?
    C10 N2 . 1.380(3) ?
    C10 C11 . 1.402(3) ?
    C11 C12 . 1.395(3) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.376(3) ?
    C12 H12 . 0.9500 ?
    C13 N2 . 1.357(3) ?
    C13 H13 . 0.9500 ?
    N1 H1 . 0.8800 ?
    N2 H2 . 0.8800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 N1 . . 123.26(19) ?
    O1 C1 C2 . . 129.56(19) ?
    N1 C1 C2 . . 107.17(18) ?
    C9 C2 C3 . . 126.11(19) ?
    C9 C2 C1 . . 128.77(19) ?
    C3 C2 C1 . . 105.08(17) ?
    C8 C3 C4 . . 119.17(19) ?
    C8 C3 C2 . . 133.25(19) ?
    C4 C3 C2 . . 107.57(18) ?
    C5 C4 N1 . . 128.72(19) ?
    C5 C4 C3 . . 122.71(19) ?
    N1 C4 C3 . . 108.57(17) ?
    C4 C5 C6 . . 117.25(19) ?
    C4 C5 H5 . . 121.4 ?
    C6 C5 H5 . . 121.4 ?
    C7 C6 C5 . . 121.2(2) ?
    C7 C6 H6 . . 119.4 ?
    C5 C6 H6 . . 119.4 ?
    C6 C7 C8 . . 120.8(2) ?
    C6 C7 H7 . . 119.6 ?
    C8 C7 H7 . . 119.6 ?
    C3 C8 C7 . . 118.86(19) ?
    C3 C8 H8 . . 120.6 ?
    C7 C8 H8 . . 120.6 ?
    C2 C9 C10 . . 131.5(2) ?
    C2 C9 H9 . . 114.3 ?
    C10 C9 H9 . . 114.3 ?
    N2 C10 C11 . . 106.43(18) ?
    N2 C10 C9 . . 125.15(19) ?
    C11 C10 C9 . . 128.4(2) ?
    C12 C11 C10 . . 107.7(2) ?
    C12 C11 H11 . . 126.1 ?
    C10 C11 H11 . . 126.1 ?
    C13 C12 C11 . . 107.6(2) ?
    C13 C12 H12 . . 126.2 ?
    C11 C12 H12 . . 126.2 ?
    N2 C13 C12 . . 108.4(2) ?
    N2 C13 H13 . . 125.8 ?
    C12 C13 H13 . . 125.8 ?
    C1 N1 C4 . . 111.60(17) ?
    C1 N1 H1 . . 124.2 ?
    C4 N1 H1 . . 124.2 ?
    C13 N2 C10 . . 109.79(18) ?
    C13 N2 H2 . . 125.1 ?
    C10 N2 H2 . . 125.1 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C9 . . . . -2.7(4) ?
    N1 C1 C2 C9 . . . . 178.0(2) ?
    O1 C1 C2 C3 . . . . 179.1(2) ?
    N1 C1 C2 C3 . . . . -0.2(2) ?
    C9 C2 C3 C8 . . . . 1.7(4) ?
    C1 C2 C3 C8 . . . . 180.0(2) ?
    C9 C2 C3 C4 . . . . -177.68(19) ?
    C1 C2 C3 C4 . . . . 0.6(2) ?
    C8 C3 C4 C5 . . . . 0.0(3) ?
    C2 C3 C4 C5 . . . . 179.53(18) ?
    C8 C3 C4 N1 . . . . 179.74(17) ?
    C2 C3 C4 N1 . . . . -0.7(2) ?
    N1 C4 C5 C6 . . . . -178.78(19) ?
    C3 C4 C5 C6 . . . . 0.9(3) ?
    C4 C5 C6 C7 . . . . -0.9(3) ?
    C5 C6 C7 C8 . . . . -0.1(3) ?
    C4 C3 C8 C7 . . . . -1.0(3) ?
    C2 C3 C8 C7 . . . . 179.7(2) ?
    C6 C7 C8 C3 . . . . 1.0(3) ?
    C3 C2 C9 C10 . . . . 175.3(2) ?
    C1 C2 C9 C10 . . . . -2.6(4) ?
    C2 C9 C10 N2 . . . . 0.3(4) ?
    C2 C9 C10 C11 . . . . -177.8(2) ?
    N2 C10 C11 C12 . . . . -0.3(2) ?
    C9 C10 C11 C12 . . . . 178.0(2) ?
    C10 C11 C12 C13 . . . . 0.1(3) ?
    C11 C12 C13 N2 . . . . 0.1(3) ?
    O1 C1 N1 C4 . . . . -179.59(19) ?
    C2 C1 N1 C4 . . . . -0.2(2) ?
    C5 C4 N1 C1 . . . . -179.7(2) ?
    C3 C4 N1 C1 . . . . 0.6(2) ?
    C12 C13 N2 C10 . . . . -0.3(3) ?
    C11 C10 N2 C13 . . . . 0.4(2) ?
    C9 C10 N2 C13 . . . . -178.0(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 O1 5_656 0.88 1.99 2.841(2) 162.4 no
    N2 H2 O1 . 0.88 1.89 2.668(2) 147.3 no
data_2b
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
(3Z)-3-(2-thienylmethylidene)-1H-indol-2(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H9 N O S'
_chemical_formula_sum     'C13 H9 N O S'
_chemical_formula_iupac     'C13 H9 N O S'
_chemical_formula_weight     227.27
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P bcn'
_symmetry_space_group_name_Hall     '-P 2n (2a)b'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y, z-1/2'
_cell_length_a     11.9297(5)
_cell_length_b     10.8294(6)
_cell_length_c     16.6986(9)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2157.32(19)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     46939
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     slab
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.16
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.399
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     944
_exptl_absorpt_coefficient_mu     0.274
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min     0.9575
_exptl_absorpt_correction_T_max     0.9891
_exptl_special_details
;
SADABS was used to perform the Absorption correction. Parameter
refinement on 16643 reflections reduced R(int) from 0.0936 to 0.0503.
Ratio of minimum to maximum apparent transmission: 0.728929. The given Tmin
and Tmax were generated using the SHELX SIZE command.
NMR spectra were measured on a Jeol EX270 spectrometer at 270 MHz (¹H) and 68
MHz (¹³C) in CDCl₃. High-resolution mass spectra were performed by the
EPSRC facility, Swansea University, Wales. ¹H NMR (270 MHz, DMSO-d₆, δ,
p.p.m.): 10.59 (1H, s), 8.10 (1H, s), 7.94--7.87 (2H, m), 7.68 (1H, d, J =
7.34 Hz), 7.24--7.19 (2H, m), 7.01--6.83 (2H, m). ¹³C NMR (75 MHz, CDCl₃,
δ, p.p.m.): 167.9, 137.7, 137.0, 133.6, 129.6, 128.4, 127.4,124.8, 123.7,
121.9, 121.7, 118.9, 109.6.
IR (KBr, ν, cm⁻¹): 3100, 1685, 1466, 1201, 716.
HRMS: m/z calculated for C₁₃H₁₀NOS (MH+) 228.0480, found
228.0478.
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     '10cm confocal mirrors'
_diffrn_measurement_device_type
                               'Bruker Nonius APEXII CCD camera on κ-goniostat'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     '4096x4096pixels / 62x62mm'
_diffrn_reflns_number     18202
_diffrn_reflns_av_R_equivalents     0.0516
_diffrn_reflns_av_sigmaI/netI     0.0352
_diffrn_reflns_theta_min     2.98
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2463
_reflns_number_gt     2024
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0706
_refine_ls_R_factor_gt     0.0539
_refine_ls_wR_factor_gt     0.1130
_refine_ls_wR_factor_ref     0.1245
_refine_ls_goodness_of_fit_ref     1.094
_refine_ls_restrained_S_all     1.094
_refine_ls_number_reflns     2463
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0321P)²+3.5864P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.337
_refine_diff_density_min     -0.420
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Version 2.01; Farrugia, 1997) and
Mercury (Version 1.4.2; Macrae et al., 2006)
;
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.65085(19) 0.4162(2) 0.50015(13) 0.0220(5) Uani d . 1 . .
    C C2 0.77266(18) 0.3870(2) 0.49670(13) 0.0205(5) Uani d . 1 . .
    C C3 0.81959(19) 0.4731(2) 0.43817(13) 0.0213(5) Uani d . 1 . .
    C C4 0.73267(19) 0.5500(2) 0.41174(13) 0.0222(5) Uani d . 1 . .
    C C5 0.7500(2) 0.6466(2) 0.35913(13) 0.0259(5) Uani d . 1 . .
    H H5 0.6902 0.6986 0.3426 0.031 Uiso calc R 1 . .
    C C6 0.8587(2) 0.6644(2) 0.33141(14) 0.0271(5) Uani d . 1 . .
    H H6 0.8738 0.7306 0.2957 0.033 Uiso calc R 1 . .
    C C7 0.9461(2) 0.5871(2) 0.35508(14) 0.0262(5) Uani d . 1 . .
    H H7 1.0191 0.5999 0.3339 0.031 Uiso calc R 1 . .
    C C8 0.92779(19) 0.4912(2) 0.40940(14) 0.0240(5) Uani d . 1 . .
    H H8 0.9877 0.4396 0.4263 0.029 Uiso calc R 1 . .
    C C9 0.83039(18) 0.3019(2) 0.53926(13) 0.0206(4) Uani d . 1 . .
    H H9 0.9073 0.2979 0.5248 0.025 Uiso calc R 1 . .
    C C10 0.80113(19) 0.2164(2) 0.60130(14) 0.0232(5) Uani d . 1 . .
    C C11 0.8803(2) 0.1355(2) 0.63514(14) 0.0264(5) Uani d . 1 . .
    H H11 0.9564 0.1316 0.6187 0.032 Uiso calc R 1 . .
    C C12 0.8344(2) 0.0609(2) 0.69595(15) 0.0311(6) Uani d . 1 . .
    H H12 0.8757 -0.0001 0.7243 0.037 Uiso calc R 1 . .
    C C13 0.7241(2) 0.0860(2) 0.70963(16) 0.0321(6) Uani d . 1 . .
    H H13 0.6805 0.0451 0.7492 0.039 Uiso calc R 1 . .
    N N1 0.63252(16) 0.51210(19) 0.44863(12) 0.0239(4) Uani d . 1 . .
    H H1 0.5666 0.5458 0.4397 0.029 Uiso calc R 1 . .
    O O1 0.57703(13) 0.36550(16) 0.54084(10) 0.0275(4) Uani d . 1 . .
    S S1 0.67228(5) 0.19836(6) 0.64842(4) 0.02905(18) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.240(3) ?
    C1 N1 . 1.366(3) ?
    C1 C2 . 1.488(3) ?
    C2 C9 . 1.352(3) ?
    C2 C3 . 1.463(3) ?
    C3 C8 . 1.391(3) ?
    C3 C4 . 1.401(3) ?
    C4 C5 . 1.382(3) ?
    C4 N1 . 1.405(3) ?
    C5 C6 . 1.390(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.394(4) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.396(3) ?
    C7 H7 . 0.9500 ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.432(3) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.407(3) ?
    C10 S1 . 1.738(2) ?
    C11 C12 . 1.408(3) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.364(4) ?
    C12 H12 . 0.9500 ?
    C13 S1 . 1.705(3) ?
    C13 H13 . 0.9500 ?
    N1 H1 . 0.8800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 N1 . . 124.6(2) ?
    O1 C1 C2 . . 128.3(2) ?
    N1 C1 C2 . . 107.08(19) ?
    C9 C2 C3 . . 126.2(2) ?
    C9 C2 C1 . . 128.5(2) ?
    C3 C2 C1 . . 105.29(19) ?
    C8 C3 C4 . . 119.7(2) ?
    C8 C3 C2 . . 132.5(2) ?
    C4 C3 C2 . . 107.83(19) ?
    C5 C4 C3 . . 122.6(2) ?
    C5 C4 N1 . . 128.8(2) ?
    C3 C4 N1 . . 108.5(2) ?
    C4 C5 C6 . . 117.2(2) ?
    C4 C5 H5 . . 121.4 ?
    C6 C5 H5 . . 121.4 ?
    C5 C6 C7 . . 121.3(2) ?
    C5 C6 H6 . . 119.4 ?
    C7 C6 H6 . . 119.4 ?
    C6 C7 C8 . . 120.9(2) ?
    C6 C7 H7 . . 119.5 ?
    C8 C7 H7 . . 119.5 ?
    C3 C8 C7 . . 118.3(2) ?
    C3 C8 H8 . . 120.9 ?
    C7 C8 H8 . . 120.9 ?
    C2 C9 C10 . . 134.1(2) ?
    C2 C9 H9 . . 112.9 ?
    C10 C9 H9 . . 112.9 ?
    C11 C10 C9 . . 122.0(2) ?
    C11 C10 S1 . . 109.97(18) ?
    C9 C10 S1 . . 128.01(18) ?
    C10 C11 C12 . . 112.7(2) ?
    C10 C11 H11 . . 123.6 ?
    C12 C11 H11 . . 123.6 ?
    C13 C12 C11 . . 112.4(2) ?
    C13 C12 H12 . . 123.8 ?
    C11 C12 H12 . . 123.8 ?
    C12 C13 S1 . . 113.1(2) ?
    C12 C13 H13 . . 123.5 ?
    S1 C13 H13 . . 123.5 ?
    C1 N1 C4 . . 111.20(19) ?
    C1 N1 H1 . . 124.4 ?
    C4 N1 H1 . . 124.4 ?
    C13 S1 C10 . . 91.79(12) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C9 . . . . -2.7(4) ?
    N1 C1 C2 C9 . . . . 177.5(2) ?
    O1 C1 C2 C3 . . . . 178.9(2) ?
    N1 C1 C2 C3 . . . . -0.9(2) ?
    C9 C2 C3 C8 . . . . 1.4(4) ?
    C1 C2 C3 C8 . . . . 179.9(2) ?
    C9 C2 C3 C4 . . . . -176.4(2) ?
    C1 C2 C3 C4 . . . . 2.1(2) ?
    C8 C3 C4 C5 . . . . -1.8(3) ?
    C2 C3 C4 C5 . . . . 176.4(2) ?
    C8 C3 C4 N1 . . . . 179.3(2) ?
    C2 C3 C4 N1 . . . . -2.5(2) ?
    C3 C4 C5 C6 . . . . 1.1(3) ?
    N1 C4 C5 C6 . . . . 179.8(2) ?
    C4 C5 C6 C7 . . . . 0.7(3) ?
    C5 C6 C7 C8 . . . . -1.9(4) ?
    C4 C3 C8 C7 . . . . 0.6(3) ?
    C2 C3 C8 C7 . . . . -177.1(2) ?
    C6 C7 C8 C3 . . . . 1.2(3) ?
    C3 C2 C9 C10 . . . . 175.6(2) ?
    C1 C2 C9 C10 . . . . -2.6(4) ?
    C2 C9 C10 C11 . . . . 179.3(2) ?
    C2 C9 C10 S1 . . . . -3.3(4) ?
    C9 C10 C11 C12 . . . . 179.0(2) ?
    S1 C10 C11 C12 . . . . 1.2(3) ?
    C10 C11 C12 C13 . . . . -1.4(3) ?
    C11 C12 C13 S1 . . . . 1.0(3) ?
    O1 C1 N1 C4 . . . . 179.6(2) ?
    C2 C1 N1 C4 . . . . -0.6(2) ?
    C5 C4 N1 C1 . . . . -176.8(2) ?
    C3 C4 N1 C1 . . . . 2.0(3) ?
    C12 C13 S1 C10 . . . . -0.3(2) ?
    C11 C10 S1 C13 . . . . -0.53(19) ?
    C9 C10 S1 C13 . . . . -178.2(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 O1 5_666 0.88 1.99 2.835(2) 160.4 no
data_3a
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
(3E)-3-(2-furylmethylidene)-1H-indol-2(3H)-one
monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H9 N O2 , H2 O'
_chemical_formula_sum     'C13 H11 N O3'
_chemical_formula_iupac     'C13 H9 N O2 , H2 O'
_chemical_formula_weight     229.23
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P bcn'
_symmetry_space_group_name_Hall     '-P 2n (2a)b'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y, z-1/2'
_cell_length_a     19.2250(7)
_cell_length_b     5.0503(3)
_cell_length_c     22.1886(14)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2154.3(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     8716
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     rod
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.06
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.413
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     960
_exptl_absorpt_coefficient_mu     0.102
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min     0.9702
_exptl_absorpt_correction_T_max     0.9959
_exptl_special_details
;
SADABS was used to perform the Absorption correction. Estimated minimum
and maximum transmission from SADABS: 0.5997 and 0.7456. The given Tmin
and Tmax were generated using the SHELX SIZE command.
NMR spectra were measured on a Jeol EX270 spectrometer at 270 MHz (¹H) and 68
MHz (¹³C) in CDCl₃. High-resolution mass spectra were performed by the
EPSRC facility, Swansea University, Wales. ¹H NMR (270 MHz, CDCl₃, δ,
p.p.m.): 8.46 (1H, d, J = 7.70 Hz), 7.77 (2H, s), 7.45 (1H, s), 7.07 (1H,
pseudo t, J = 7.70 Hz), 6.90 (2H, m), 6.63 (1H, m). ¹³C NMR (75 MHz, CDCl₃,
δ, p.p.m.): 171.0,151.4, 145.9, 141.2, 129.4, 125.1, 122.5, 122.13, 122.0,
120.5, 120.0, 113.1,109.8.
IR (KBr, ν, cm⁻¹): 3139, 1702, 1227, 1031, 745.
HRMS: m/z calculated for C₁₃H₁₂NO₃ (MH+) 212.0706, found
212.0706.
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type
                                'Bruker Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     13065
_diffrn_reflns_av_R_equivalents     0.0852
_diffrn_reflns_av_sigmaI/netI     0.0636
_diffrn_reflns_theta_min     3.67
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     1881
_reflns_number_gt     1355
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0854
_refine_ls_R_factor_gt     0.0518
_refine_ls_wR_factor_gt     0.1057
_refine_ls_wR_factor_ref     0.1175
_refine_ls_goodness_of_fit_ref     1.064
_refine_ls_restrained_S_all     1.063
_refine_ls_number_reflns     1881
_refine_ls_number_parameters     160
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0432P)²+1.1222P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.237
_refine_diff_density_min     -0.248
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Version 2.01; Farrugia, 1997) and
Mercury (Version 1.4.2; Macrae et al., 2006)
;
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.47350(11) -0.1896(5) 0.05249(11) 0.0217(6) Uani d . 1 . .
    C C2 0.47019(11) 0.0306(4) 0.09706(11) 0.0204(6) Uani d . 1 . .
    C C3 0.53956(11) 0.0371(5) 0.12558(11) 0.0218(6) Uani d . 1 . .
    C C4 0.57891(11) -0.1658(5) 0.09850(11) 0.0208(6) Uani d . 1 . .
    C C5 0.64777(11) -0.2112(5) 0.11202(11) 0.0237(6) Uani d . 1 . .
    H H5 0.6732 -0.3485 0.0928 0.028 Uiso calc R 1 . .
    C C6 0.67857(11) -0.0483(5) 0.15485(12) 0.0247(6) Uani d . 1 . .
    H H6 0.7261 -0.0738 0.1650 0.030 Uiso calc R 1 . .
    C C7 0.64096(12) 0.1510(5) 0.18295(11) 0.0233(6) Uani d . 1 . .
    H H7 0.6629 0.2589 0.2124 0.028 Uiso calc R 1 . .
    C C8 0.57162(11) 0.1945(5) 0.16843(11) 0.0221(6) Uani d . 1 . .
    H H8 0.5463 0.3318 0.1878 0.027 Uiso calc R 1 . .
    C C9 0.41034(11) 0.1692(5) 0.10262(11) 0.0226(6) Uani d . 1 . .
    H H9 0.3754 0.1164 0.0748 0.027 Uiso calc R 1 . .
    C C10 0.38905(11) 0.3767(5) 0.14126(11) 0.0221(6) Uani d . 1 . .
    C C11 0.32701(11) 0.5065(5) 0.14502(11) 0.0241(6) Uani d . 1 . .
    H H11 0.2874 0.4777 0.1203 0.029 Uiso calc R 1 . .
    C C12 0.33264(12) 0.6919(5) 0.19250(12) 0.0262(6) Uani d . 1 . .
    H H12 0.2975 0.8103 0.2060 0.031 Uiso calc R 1 . .
    C C13 0.39748(12) 0.6683(5) 0.21495(12) 0.0266(6) Uani d . 1 . .
    H H13 0.4156 0.7707 0.2473 0.032 Uiso calc R 1 . .
    N N1 0.53748(9) -0.2997(4) 0.05613(9) 0.0235(5) Uani d . 1 . .
    H H1 0.5513 -0.4368 0.0348 0.028 Uiso calc R 1 . .
    O O1 0.42676(8) -0.2639(3) 0.01749(7) 0.0254(4) Uani d . 1 . .
    O O2 0.43349(8) 0.4766(3) 0.18474(7) 0.0260(4) Uani d . 1 . .
    O O101 0.27917(10) -0.2601(4) 0.00470(12) 0.0518(6) Uani d D 1 . .
    H H1W 0.2631(15) -0.100(4) 0.0018(16) 0.078 Uiso d D 1 . .
    H H2W 0.3234(9) -0.246(6) 0.0087(16) 0.078 Uiso d D 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.246(3) ?
    C1 N1 . 1.352(3) ?
    C1 C2 . 1.489(3) ?
    C2 C9 . 1.353(3) ?
    C2 C3 . 1.477(3) ?
    C3 C8 . 1.384(3) ?
    C3 C4 . 1.408(3) ?
    C4 C5 . 1.377(3) ?
    C4 N1 . 1.406(3) ?
    C5 C6 . 1.389(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.387(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.389(3) ?
    C7 H7 . 0.9500 ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.414(3) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.364(3) ?
    C10 O2 . 1.384(3) ?
    C11 C12 . 1.414(4) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.348(3) ?
    C12 H12 . 0.9500 ?
    C13 O2 . 1.366(3) ?
    C13 H13 . 0.9500 ?
    N1 H1 . 0.8800 ?
    O101 H1W . 0.870(18) ?
    O101 H2W . 0.858(17) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 N1 . . 124.7(2) ?
    O1 C1 C2 . . 127.4(2) ?
    N1 C1 C2 . . 107.8(2) ?
    C9 C2 C3 . . 135.9(2) ?
    C9 C2 C1 . . 118.9(2) ?
    C3 C2 C1 . . 105.23(19) ?
    C8 C3 C4 . . 118.2(2) ?
    C8 C3 C2 . . 135.2(2) ?
    C4 C3 C2 . . 106.6(2) ?
    C5 C4 N1 . . 127.6(2) ?
    C5 C4 C3 . . 123.0(2) ?
    N1 C4 C3 . . 109.33(19) ?
    C4 C5 C6 . . 117.4(2) ?
    C4 C5 H5 . . 121.3 ?
    C6 C5 H5 . . 121.3 ?
    C7 C6 C5 . . 121.0(2) ?
    C7 C6 H6 . . 119.5 ?
    C5 C6 H6 . . 119.5 ?
    C6 C7 C8 . . 120.7(2) ?
    C6 C7 H7 . . 119.6 ?
    C8 C7 H7 . . 119.6 ?
    C3 C8 C7 . . 119.7(2) ?
    C3 C8 H8 . . 120.1 ?
    C7 C8 H8 . . 120.1 ?
    C2 C9 C10 . . 133.2(2) ?
    C2 C9 H9 . . 113.4 ?
    C10 C9 H9 . . 113.4 ?
    C11 C10 O2 . . 108.8(2) ?
    C11 C10 C9 . . 130.3(2) ?
    O2 C10 C9 . . 120.9(2) ?
    C10 C11 C12 . . 107.3(2) ?
    C10 C11 H11 . . 126.4 ?
    C12 C11 H11 . . 126.4 ?
    C13 C12 C11 . . 106.7(2) ?
    C13 C12 H12 . . 126.6 ?
    C11 C12 H12 . . 126.6 ?
    C12 C13 O2 . . 110.5(2) ?
    C12 C13 H13 . . 124.8 ?
    O2 C13 H13 . . 124.8 ?
    C1 N1 C4 . . 111.0(2) ?
    C1 N1 H1 . . 124.5 ?
    C4 N1 H1 . . 124.5 ?
    C13 O2 C10 . . 106.72(17) ?
    H1W O101 H2W . . 106(2) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C9 . . . . 1.2(4) ?
    N1 C1 C2 C9 . . . . -178.9(2) ?
    O1 C1 C2 C3 . . . . -178.9(2) ?
    N1 C1 C2 C3 . . . . 1.1(2) ?
    C9 C2 C3 C8 . . . . -2.4(5) ?
    C1 C2 C3 C8 . . . . 177.7(3) ?
    C9 C2 C3 C4 . . . . -179.9(3) ?
    C1 C2 C3 C4 . . . . 0.1(2) ?
    C8 C3 C4 C5 . . . . -1.1(4) ?
    C2 C3 C4 C5 . . . . 177.0(2) ?
    C8 C3 C4 N1 . . . . -179.3(2) ?
    C2 C3 C4 N1 . . . . -1.3(3) ?
    N1 C4 C5 C6 . . . . 178.5(2) ?
    C3 C4 C5 C6 . . . . 0.6(4) ?
    C4 C5 C6 C7 . . . . 0.3(4) ?
    C5 C6 C7 C8 . . . . -0.7(4) ?
    C4 C3 C8 C7 . . . . 0.7(3) ?
    C2 C3 C8 C7 . . . . -176.7(2) ?
    C6 C7 C8 C3 . . . . 0.2(3) ?
    C3 C2 C9 C10 . . . . -3.1(5) ?
    C1 C2 C9 C10 . . . . 176.8(2) ?
    C2 C9 C10 C11 . . . . -179.0(3) ?
    C2 C9 C10 O2 . . . . -0.4(4) ?
    O2 C10 C11 C12 . . . . -0.4(3) ?
    C9 C10 C11 C12 . . . . 178.4(2) ?
    C10 C11 C12 C13 . . . . 0.5(3) ?
    C11 C12 C13 O2 . . . . -0.4(3) ?
    O1 C1 N1 C4 . . . . 178.1(2) ?
    C2 C1 N1 C4 . . . . -1.9(3) ?
    C5 C4 N1 C1 . . . . -176.1(2) ?
    C3 C4 N1 C1 . . . . 2.0(3) ?
    C12 C13 O2 C10 . . . . 0.2(3) ?
    C11 C10 O2 C13 . . . . 0.1(3) ?
    C9 C10 O2 C13 . . . . -178.8(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 O1 5_645 0.88 1.95 2.828(3) 174.0 no
    O101 H1W O101 7_665 0.870(18) 1.899(18) 2.7630(15) 172(3) no
    O101 H2W O1 . 0.858(17) 1.999(17) 2.852(2) 173(3) no
data_4a
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
3-(1-methylethylidene)-1H-indol-2(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H11 N O'
_chemical_formula_sum     'C11 H11 N O'
_chemical_formula_iupac     'C11 H11 N O'
_chemical_formula_weight     173.21
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.7504(3)
_cell_length_b     10.2281(3)
_cell_length_c     14.0530(5)
_cell_angle_alpha     95.766(2)
_cell_angle_beta     107.842(2)
_cell_angle_gamma     96.617(2)
_cell_volume     1311.45(7)
_cell_formula_units_Z     6
_cell_measurement_reflns_used     16164
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'light orange'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.316
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     552
_exptl_absorpt_coefficient_mu     0.085
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min     0.9750
_exptl_absorpt_correction_T_max     0.9966
_exptl_special_details
;
SADABS was used to perform the Absorption correction. Parameter
refinement on 16695 reflections reduced R(int) from 0.1392 to 0.0541.
Ratio of minimum to maximum apparent transmission: 0.857568. The given Tmin
and Tmax were generated using the SHELX SIZE command.
NMR spectra were measured on a Jeol EX270 spectrometer at 270 MHz (¹H) and 68
MHz (¹³C) in CDCl₃. High-resolution mass spectra were performed by the
EPSRC facility, Swansea University, Wales. ¹H NMR (270 MHz, CDCl₃, δ,
p.p.m.): 7.91 (1H, s), 7.53--6.83 (4H, m), 2.61 (3H, s), 2.38 (3H, s).
¹³C NMR (75 MHz, CDCl₃, δ, p.p.m.): 169.6, 155.5, 139.3, 127.5, 124.3,
123.6, 123.0, 121.5, 109.3, 25.2, 23.1.
IR (KBr, ν, cm⁻¹): 3154, 1674, 1271, 817.
HRMS: m/z calculated for C₁₁H₁₂NO (MH+) 174.0913, found
174.0912.
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     '10cm confocal mirrors'
_diffrn_measurement_device_type
                               'Bruker Nonius APEXII CCD camera on κ-goniostat'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     '4096x4096pixels / 62x62mm'
_diffrn_reflns_number     21390
_diffrn_reflns_av_R_equivalents     0.0592
_diffrn_reflns_av_sigmaI/netI     0.0674
_diffrn_reflns_theta_min     2.95
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     5972
_reflns_number_gt     4122
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1204
_refine_ls_R_factor_gt     0.0788
_refine_ls_wR_factor_gt     0.1445
_refine_ls_wR_factor_ref     0.1681
_refine_ls_goodness_of_fit_ref     1.077
_refine_ls_restrained_S_all     1.077
_refine_ls_number_reflns     5972
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0214P)²+2.3372P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.356
_refine_diff_density_min     -0.312
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Version 2.01; Farrugia, 1997) and
Mercury (Version 1.4.2; Macrae et al., 2006)
;
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.9147(3) 0.0015(2) 0.3484(2) 0.0191(5) Uani d . 1 . .
    C C2 0.8145(3) 0.0030(2) 0.24248(19) 0.0185(5) Uani d . 1 . .
    C C3 0.6692(3) 0.0080(2) 0.25253(19) 0.0185(5) Uani d . 1 . .
    C C4 0.6851(3) 0.0091(2) 0.3554(2) 0.0198(6) Uani d . 1 . .
    C C5 0.5695(3) 0.0098(3) 0.3926(2) 0.0250(6) Uani d . 1 . .
    H H5 0.5836 0.0113 0.4626 0.030 Uiso calc R 1 . .
    C C6 0.4314(3) 0.0084(3) 0.3239(2) 0.0277(6) Uani d . 1 . .
    H H6 0.3497 0.0088 0.3471 0.033 Uiso calc R 1 . .
    C C7 0.4125(3) 0.0065(3) 0.2220(2) 0.0266(6) Uani d . 1 . .
    H H7 0.3175 0.0049 0.1762 0.032 Uiso calc R 1 . .
    C C8 0.5304(3) 0.0068(3) 0.1855(2) 0.0240(6) Uani d . 1 . .
    H H8 0.5159 0.0062 0.1154 0.029 Uiso calc R 1 . .
    C C9 0.8559(3) 0.0002(2) 0.1591(2) 0.0214(6) Uani d . 1 . .
    C C10 0.7509(3) 0.0086(3) 0.0571(2) 0.0263(6) Uani d . 1 . .
    H H10A 0.6692 -0.0646 0.0396 0.040 Uiso calc R 1 . .
    H H10B 0.8008 0.0021 0.0064 0.040 Uiso calc R 1 . .
    H H10C 0.7140 0.0936 0.0587 0.040 Uiso calc R 1 . .
    C C11 1.0083(3) -0.0114(3) 0.1595(2) 0.0293(7) Uani d . 1 . .
    H H11A 1.0706 -0.0132 0.2288 0.044 Uiso calc R 1 . .
    H H11B 1.0465 0.0650 0.1333 0.044 Uiso calc R 1 . .
    H H11C 1.0072 -0.0937 0.1168 0.044 Uiso calc R 1 . .
    N N1 0.8302(2) 0.0067(2) 0.40969(17) 0.0210(5) Uani d . 1 . .
    H H1 0.8635 0.0083 0.4756 0.025 Uiso calc R 1 . .
    O O1 1.0469(2) -0.00082(18) 0.37839(14) 0.0229(4) Uani d . 1 . .
    C C101 1.1804(3) 0.3134(2) 0.67501(19) 0.0190(5) Uani d . 1 . .
    C C102 1.0822(3) 0.3172(2) 0.5693(2) 0.0193(5) Uani d . 1 . .
    C C103 0.9363(3) 0.3213(2) 0.57864(19) 0.0192(6) Uani d . 1 . .
    C C104 0.9502(3) 0.3190(2) 0.6811(2) 0.0212(6) Uani d . 1 . .
    C C105 0.8340(3) 0.3202(3) 0.7174(2) 0.0257(6) Uani d . 1 . .
    H H105 0.8472 0.3190 0.7871 0.031 Uiso calc R 1 . .
    C C106 0.6973(3) 0.3231(3) 0.6493(2) 0.0280(6) Uani d . 1 . .
    H H106 0.6155 0.3240 0.6724 0.034 Uiso calc R 1 . .
    C C107 0.6796(3) 0.3249(3) 0.5477(2) 0.0291(6) Uani d . 1 . .
    H H107 0.5854 0.3269 0.5019 0.035 Uiso calc R 1 . .
    C C108 0.7983(3) 0.3238(3) 0.5115(2) 0.0268(6) Uani d . 1 . .
    H H108 0.7848 0.3247 0.4417 0.032 Uiso calc R 1 . .
    C C109 1.1276(3) 0.3190(2) 0.4874(2) 0.0213(6) Uani d . 1 . .
    C C110 1.0276(3) 0.3347(3) 0.3856(2) 0.0314(7) Uani d . 1 . .
    H H11D 0.9703 0.2482 0.3516 0.047 Uiso calc R 1 . .
    H H11E 1.0855 0.3687 0.3448 0.047 Uiso calc R 1 . .
    H H11F 0.9618 0.3973 0.3937 0.047 Uiso calc R 1 . .
    C C111 1.2798(3) 0.3054(3) 0.4896(2) 0.0290(7) Uani d . 1 . .
    H H11G 1.3339 0.2812 0.5549 0.043 Uiso calc R 1 . .
    H H11H 1.3284 0.3901 0.4802 0.043 Uiso calc R 1 . .
    H H11I 1.2766 0.2360 0.4353 0.043 Uiso calc R 1 . .
    N N101 1.0952(2) 0.3153(2) 0.73532(17) 0.0216(5) Uani d . 1 . .
    H H101 1.1277 0.3143 0.8009 0.026 Uiso calc R 1 . .
    O O101 1.3130(2) 0.31170(18) 0.70609(14) 0.0242(4) Uani d . 1 . .
    C C201 1.3470(3) 0.3250(2) 0.9789(2) 0.0202(6) Uani d . 1 . .
    C C202 1.4479(3) 0.3417(2) 1.0863(2) 0.0194(5) Uani d . 1 . .
    C C203 1.5959(3) 0.3479(2) 1.0787(2) 0.0200(6) Uani d . 1 . .
    C C204 1.5804(3) 0.3330(2) 0.9751(2) 0.0202(6) Uani d . 1 . .
    C C205 1.6974(3) 0.3345(3) 0.9397(2) 0.0243(6) Uani d . 1 . .
    H H205 1.6835 0.3230 0.8693 0.029 Uiso calc R 1 . .
    C C206 1.8367(3) 0.3533(3) 1.0099(2) 0.0258(6) Uani d . 1 . .
    H H206 1.9194 0.3558 0.9875 0.031 Uiso calc R 1 . .
    C C207 1.8552(3) 0.3686(3) 1.1127(2) 0.0279(6) Uani d . 1 . .
    H H207 1.9509 0.3813 1.1598 0.033 Uiso calc R 1 . .
    C C208 1.7363(3) 0.3658(3) 1.1479(2) 0.0246(6) Uani d . 1 . .
    H H208 1.7506 0.3759 1.2183 0.030 Uiso calc R 1 . .
    C C209 1.4052(3) 0.3485(2) 1.1693(2) 0.0204(6) Uani d . 1 . .
    C C210 1.5128(3) 0.3655(3) 1.2744(2) 0.0283(6) Uani d . 1 . .
    H H21A 1.5684 0.2911 1.2811 0.043 Uiso calc R 1 . .
    H H21B 1.4603 0.3674 1.3237 0.043 Uiso calc R 1 . .
    H H21C 1.5797 0.4492 1.2867 0.043 Uiso calc R 1 . .
    C C211 1.2486(3) 0.3408(3) 1.1650(2) 0.0288(6) Uani d . 1 . .
    H H21D 1.1857 0.3261 1.0944 0.043 Uiso calc R 1 . .
    H H21E 1.2346 0.4243 1.1990 0.043 Uiso calc R 1 . .
    H H21F 1.2232 0.2670 1.1990 0.043 Uiso calc R 1 . .
    N N201 1.4328(2) 0.3184(2) 0.91886(17) 0.0212(5) Uani d . 1 . .
    H H201 1.3992 0.3063 0.8524 0.025 Uiso calc R 1 . .
    O O201 1.2127(2) 0.31515(18) 0.94666(14) 0.0236(4) Uani d . 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.232(3) ?
    C1 N1 . 1.363(3) ?
    C1 C2 . 1.512(4) ?
    C2 C9 . 1.351(4) ?
    C2 C3 . 1.472(4) ?
    C3 C8 . 1.390(4) ?
    C3 C4 . 1.404(3) ?
    C4 C5 . 1.381(4) ?
    C4 N1 . 1.391(3) ?
    C5 C6 . 1.393(4) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.384(4) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.395(4) ?
    C7 H7 . 0.9500 ?
    C8 H8 . 0.9500 ?
    C9 C11 . 1.502(4) ?
    C9 C10 . 1.502(4) ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    N1 H1 . 0.8800 ?
    C101 O101 . 1.234(3) ?
    C101 N101 . 1.357(3) ?
    C101 C102 . 1.508(4) ?
    C102 C109 . 1.355(4) ?
    C102 C103 . 1.473(4) ?
    C103 C108 . 1.391(4) ?
    C103 C104 . 1.407(4) ?
    C104 C105 . 1.378(4) ?
    C104 N101 . 1.393(3) ?
    C105 C106 . 1.388(4) ?
    C105 H105 . 0.9500 ?
    C106 C107 . 1.386(4) ?
    C106 H106 . 0.9500 ?
    C107 C108 . 1.401(4) ?
    C107 H107 . 0.9500 ?
    C108 H108 . 0.9500 ?
    C109 C111 . 1.497(4) ?
    C109 C110 . 1.500(4) ?
    C110 H11D . 0.9800 ?
    C110 H11E . 0.9800 ?
    C110 H11F . 0.9800 ?
    C111 H11G . 0.9800 ?
    C111 H11H . 0.9800 ?
    C111 H11I . 0.9800 ?
    N101 H101 . 0.8800 ?
    C201 O201 . 1.235(3) ?
    C201 N201 . 1.360(3) ?
    C201 C202 . 1.509(4) ?
    C202 C209 . 1.351(4) ?
    C202 C203 . 1.474(4) ?
    C203 C208 . 1.394(4) ?
    C203 C204 . 1.408(4) ?
    C204 C205 . 1.376(4) ?
    C204 N201 . 1.396(3) ?
    C205 C206 . 1.390(4) ?
    C205 H205 . 0.9500 ?
    C206 C207 . 1.390(4) ?
    C206 H206 . 0.9500 ?
    C207 C208 . 1.391(4) ?
    C207 H207 . 0.9500 ?
    C208 H208 . 0.9500 ?
    C209 C211 . 1.502(4) ?
    C209 C210 . 1.507(4) ?
    C210 H21A . 0.9800 ?
    C210 H21B . 0.9800 ?
    C210 H21C . 0.9800 ?
    C211 H21D . 0.9800 ?
    C211 H21E . 0.9800 ?
    C211 H21F . 0.9800 ?
    N201 H201 . 0.8800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 N1 . . 124.2(2) ?
    O1 C1 C2 . . 129.4(2) ?
    N1 C1 C2 . . 106.4(2) ?
    C9 C2 C3 . . 129.6(2) ?
    C9 C2 C1 . . 125.2(2) ?
    C3 C2 C1 . . 105.3(2) ?
    C8 C3 C4 . . 118.2(2) ?
    C8 C3 C2 . . 134.9(2) ?
    C4 C3 C2 . . 106.8(2) ?
    C5 C4 N1 . . 127.3(2) ?
    C5 C4 C3 . . 123.0(3) ?
    N1 C4 C3 . . 109.8(2) ?
    C4 C5 C6 . . 117.7(3) ?
    C4 C5 H5 . . 121.1 ?
    C6 C5 H5 . . 121.1 ?
    C7 C6 C5 . . 120.5(3) ?
    C7 C6 H6 . . 119.8 ?
    C5 C6 H6 . . 119.8 ?
    C6 C7 C8 . . 121.2(3) ?
    C6 C7 H7 . . 119.4 ?
    C8 C7 H7 . . 119.4 ?
    C3 C8 C7 . . 119.4(3) ?
    C3 C8 H8 . . 120.3 ?
    C7 C8 H8 . . 120.3 ?
    C2 C9 C11 . . 123.7(3) ?
    C2 C9 C10 . . 121.9(3) ?
    C11 C9 C10 . . 114.4(2) ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C9 C11 H11A . . 109.5 ?
    C9 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C9 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C1 N1 C4 . . 111.7(2) ?
    C1 N1 H1 . . 124.1 ?
    C4 N1 H1 . . 124.1 ?
    O101 C101 N101 . . 123.8(2) ?
    O101 C101 C102 . . 129.5(2) ?
    N101 C101 C102 . . 106.7(2) ?
    C109 C102 C103 . . 130.4(3) ?
    C109 C102 C101 . . 124.5(2) ?
    C103 C102 C101 . . 105.1(2) ?
    C108 C103 C104 . . 118.0(2) ?
    C108 C103 C102 . . 135.0(2) ?
    C104 C103 C102 . . 107.0(2) ?
    C105 C104 N101 . . 127.7(3) ?
    C105 C104 C103 . . 123.0(3) ?
    N101 C104 C103 . . 109.3(2) ?
    C104 C105 C106 . . 118.2(3) ?
    C104 C105 H105 . . 120.9 ?
    C106 C105 H105 . . 120.9 ?
    C107 C106 C105 . . 120.4(3) ?
    C107 C106 H106 . . 119.8 ?
    C105 C106 H106 . . 119.8 ?
    C106 C107 C108 . . 121.0(3) ?
    C106 C107 H107 . . 119.5 ?
    C108 C107 H107 . . 119.5 ?
    C103 C108 C107 . . 119.4(3) ?
    C103 C108 H108 . . 120.3 ?
    C107 C108 H108 . . 120.3 ?
    C102 C109 C111 . . 123.7(3) ?
    C102 C109 C110 . . 122.2(3) ?
    C111 C109 C110 . . 114.1(2) ?
    C109 C110 H11D . . 109.5 ?
    C109 C110 H11E . . 109.5 ?
    H11D C110 H11E . . 109.5 ?
    C109 C110 H11F . . 109.5 ?
    H11D C110 H11F . . 109.5 ?
    H11E C110 H11F . . 109.5 ?
    C109 C111 H11G . . 109.5 ?
    C109 C111 H11H . . 109.5 ?
    H11G C111 H11H . . 109.5 ?
    C109 C111 H11I . . 109.5 ?
    H11G C111 H11I . . 109.5 ?
    H11H C111 H11I . . 109.5 ?
    C101 N101 C104 . . 112.0(2) ?
    C101 N101 H101 . . 124.0 ?
    C104 N101 H101 . . 124.0 ?
    O201 C201 N201 . . 124.0(2) ?
    O201 C201 C202 . . 129.6(2) ?
    N201 C201 C202 . . 106.4(2) ?
    C209 C202 C203 . . 129.5(3) ?
    C209 C202 C201 . . 125.1(2) ?
    C203 C202 C201 . . 105.4(2) ?
    C208 C203 C204 . . 118.2(2) ?
    C208 C203 C202 . . 135.0(2) ?
    C204 C203 C202 . . 106.8(2) ?
    C205 C204 N201 . . 127.9(2) ?
    C205 C204 C203 . . 122.8(3) ?
    N201 C204 C203 . . 109.3(2) ?
    C204 C205 C206 . . 118.2(3) ?
    C204 C205 H205 . . 120.9 ?
    C206 C205 H205 . . 120.9 ?
    C207 C206 C205 . . 120.2(3) ?
    C207 C206 H206 . . 119.9 ?
    C205 C206 H206 . . 119.9 ?
    C206 C207 C208 . . 121.3(3) ?
    C206 C207 H207 . . 119.4 ?
    C208 C207 H207 . . 119.4 ?
    C207 C208 C203 . . 119.4(3) ?
    C207 C208 H208 . . 120.3 ?
    C203 C208 H208 . . 120.3 ?
    C202 C209 C211 . . 123.4(3) ?
    C202 C209 C210 . . 122.0(3) ?
    C211 C209 C210 . . 114.6(2) ?
    C209 C210 H21A . . 109.5 ?
    C209 C210 H21B . . 109.5 ?
    H21A C210 H21B . . 109.5 ?
    C209 C210 H21C . . 109.5 ?
    H21A C210 H21C . . 109.5 ?
    H21B C210 H21C . . 109.5 ?
    C209 C211 H21D . . 109.5 ?
    C209 C211 H21E . . 109.5 ?
    H21D C211 H21E . . 109.5 ?
    C209 C211 H21F . . 109.5 ?
    H21D C211 H21F . . 109.5 ?
    H21E C211 H21F . . 109.5 ?
    C201 N201 C204 . . 112.0(2) ?
    C201 N201 H201 . . 124.0 ?
    C204 N201 H201 . . 124.0 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C9 . . . . 0.9(4) ?
    N1 C1 C2 C9 . . . . 179.4(2) ?
    O1 C1 C2 C3 . . . . -179.1(2) ?
    N1 C1 C2 C3 . . . . -0.6(3) ?
    C9 C2 C3 C8 . . . . 2.8(5) ?
    C1 C2 C3 C8 . . . . -177.3(3) ?
    C9 C2 C3 C4 . . . . 180.0(3) ?
    C1 C2 C3 C4 . . . . -0.1(3) ?
    C8 C3 C4 C5 . . . . -0.5(4) ?
    C2 C3 C4 C5 . . . . -178.2(2) ?
    C8 C3 C4 N1 . . . . 178.4(2) ?
    C2 C3 C4 N1 . . . . 0.7(3) ?
    N1 C4 C5 C6 . . . . -178.2(3) ?
    C3 C4 C5 C6 . . . . 0.5(4) ?
    C4 C5 C6 C7 . . . . -0.1(4) ?
    C5 C6 C7 C8 . . . . -0.4(4) ?
    C4 C3 C8 C7 . . . . -0.1(4) ?
    C2 C3 C8 C7 . . . . 176.8(3) ?
    C6 C7 C8 C3 . . . . 0.5(4) ?
    C3 C2 C9 C11 . . . . -177.0(3) ?
    C1 C2 C9 C11 . . . . 3.1(4) ?
    C3 C2 C9 C10 . . . . 2.9(4) ?
    C1 C2 C9 C10 . . . . -177.0(2) ?
    O1 C1 N1 C4 . . . . 179.7(2) ?
    C2 C1 N1 C4 . . . . 1.0(3) ?
    C5 C4 N1 C1 . . . . 177.7(3) ?
    C3 C4 N1 C1 . . . . -1.2(3) ?
    O101 C101 C102 C109 . . . . 0.3(4) ?
    N101 C101 C102 C109 . . . . 178.8(2) ?
    O101 C101 C102 C103 . . . . -178.5(2) ?
    N101 C101 C102 C103 . . . . 0.0(3) ?
    C109 C102 C103 C108 . . . . 2.5(5) ?
    C101 C102 C103 C108 . . . . -178.8(3) ?
    C109 C102 C103 C104 . . . . -179.1(3) ?
    C101 C102 C103 C104 . . . . -0.4(3) ?
    C108 C103 C104 C105 . . . . -0.5(4) ?
    C102 C103 C104 C105 . . . . -179.2(2) ?
    C108 C103 C104 N101 . . . . 179.3(2) ?
    C102 C103 C104 N101 . . . . 0.6(3) ?
    N101 C104 C105 C106 . . . . -179.6(3) ?
    C103 C104 C105 C106 . . . . 0.3(4) ?
    C104 C105 C106 C107 . . . . 0.0(4) ?
    C105 C106 C107 C108 . . . . 0.0(4) ?
    C104 C103 C108 C107 . . . . 0.5(4) ?
    C102 C103 C108 C107 . . . . 178.7(3) ?
    C106 C107 C108 C103 . . . . -0.2(4) ?
    C103 C102 C109 C111 . . . . -175.9(3) ?
    C101 C102 C109 C111 . . . . 5.6(4) ?
    C103 C102 C109 C110 . . . . 3.9(4) ?
    C101 C102 C109 C110 . . . . -174.6(2) ?
    O101 C101 N101 C104 . . . . 179.1(2) ?
    C102 C101 N101 C104 . . . . 0.4(3) ?
    C105 C104 N101 C101 . . . . 179.2(3) ?
    C103 C104 N101 C101 . . . . -0.7(3) ?
    O201 C201 C202 C209 . . . . 0.2(4) ?
    N201 C201 C202 C209 . . . . -178.0(2) ?
    O201 C201 C202 C203 . . . . -179.9(3) ?
    N201 C201 C202 C203 . . . . 1.9(3) ?
    C209 C202 C203 C208 . . . . -2.2(5) ?
    C201 C202 C203 C208 . . . . 177.9(3) ?
    C209 C202 C203 C204 . . . . 178.6(3) ?
    C201 C202 C203 C204 . . . . -1.2(3) ?
    C208 C203 C204 C205 . . . . 0.4(4) ?
    C202 C203 C204 C205 . . . . 179.7(2) ?
    C208 C203 C204 N201 . . . . -179.2(2) ?
    C202 C203 C204 N201 . . . . 0.2(3) ?
    N201 C204 C205 C206 . . . . 178.6(2) ?
    C203 C204 C205 C206 . . . . -0.8(4) ?
    C204 C205 C206 C207 . . . . 0.7(4) ?
    C205 C206 C207 C208 . . . . -0.1(4) ?
    C206 C207 C208 C203 . . . . -0.3(4) ?
    C204 C203 C208 C207 . . . . 0.2(4) ?
    C202 C203 C208 C207 . . . . -178.9(3) ?
    C203 C202 C209 C211 . . . . 179.9(2) ?
    C201 C202 C209 C211 . . . . -0.3(4) ?
    C203 C202 C209 C210 . . . . 0.3(4) ?
    C201 C202 C209 C210 . . . . -179.8(2) ?
    O201 C201 N201 C204 . . . . 179.8(2) ?
    C202 C201 N201 C204 . . . . -1.9(3) ?
    C205 C204 N201 C201 . . . . -178.4(3) ?
    C203 C204 N201 C201 . . . . 1.1(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 O1 2_756 0.88 1.98 2.859(3) 174.2 no
    N101 H101 O201 . 0.88 1.96 2.837(3) 176.3 no
    N201 H201 O101 . 0.88 1.98 2.848(3) 169.5 no
data_4b
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
3-(1-methylethylidene)-2-oxo-2,3-dihydro-1H-indole-1-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H13 N O3'
_chemical_formula_sum     'C13 H13 N O3'
_chemical_formula_iupac     'C13 H13 N O3'
_chemical_formula_weight     231.24
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     10.6939(2)
_cell_length_b     17.2595(4)
_cell_length_c     12.7714(3)
_cell_angle_alpha     90.00
_cell_angle_beta     108.3220(10)
_cell_angle_gamma     90.00
_cell_volume     2237.73(8)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     11877
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.373
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     976
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min     0.9655
_exptl_absorpt_correction_T_max     0.9825
_exptl_special_details
;
SADABS was used to perform the Absorption correction. Estimated minimum
and maximum transmission from SADABS: 0.6574 and 0.7456. The given Tmin
and Tmax were generated using the SHELX SIZE command.
NMR spectra were measured on a Jeol EX270 spectrometer at 270 MHz (¹H) and 68
MHz (¹³C) in CDCl₃. High-resolution mass spectra were performed by the
EPSRC facility, Swansea University, Wales. ¹H NMR (270 MHz, CDCl₃, δ,
p.p.m.): 7.94 (1H, d, J = 7.90 Hz), 7.51 (1H, d, J = 7.7 Hz), 7.14 (1H, m),
7.11 (1H, m), 3.97 (3H, s), 2.55 (3H, s), 2.35 (3H, s).
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type
                                'Bruker Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     26778
_diffrn_reflns_av_R_equivalents     0.0518
_diffrn_reflns_av_sigmaI/netI     0.0433
_diffrn_reflns_theta_min     2.99
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     22
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     5129
_reflns_number_gt     3809
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0723
_refine_ls_R_factor_gt     0.0488
_refine_ls_wR_factor_gt     0.1206
_refine_ls_wR_factor_ref     0.1344
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.039
_refine_ls_number_reflns     5129
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0651P)²+0.8778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.021
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.314
_refine_diff_density_min     -0.354
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Version 2.01; Farrugia, 1997) and
Mercury (Version 1.4.2; Macrae et al., 2006)
;
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.74065(15) 0.22350(9) -0.00211(12) 0.0190(3) Uani d . 1 . .
    C C2 0.72748(15) 0.30957(9) 0.00312(12) 0.0186(3) Uani d . 1 . .
    C C3 0.64105(15) 0.32442(9) 0.06970(12) 0.0181(3) Uani d . 1 . .
    C C4 0.59946(14) 0.25290(9) 0.10028(12) 0.0178(3) Uani d . 1 . .
    C C5 0.51359(15) 0.24725(9) 0.16159(13) 0.0217(3) Uani d . 1 . .
    H H5 0.4854 0.1983 0.1798 0.026 Uiso calc R 1 . .
    C C6 0.47014(16) 0.31614(9) 0.19559(13) 0.0232(4) Uani d . 1 . .
    H H6 0.4111 0.3141 0.2377 0.028 Uiso calc R 1 . .
    C C7 0.51169(15) 0.38756(9) 0.16905(13) 0.0231(3) Uani d . 1 . .
    H H7 0.4821 0.4337 0.1944 0.028 Uiso calc R 1 . .
    C C8 0.59594(15) 0.39227(9) 0.10593(13) 0.0210(3) Uani d . 1 . .
    H H8 0.6229 0.4414 0.0874 0.025 Uiso calc R 1 . .
    C C9 0.78645(15) 0.35945(9) -0.04882(12) 0.0207(3) Uani d . 1 . .
    C C10 0.76996(18) 0.44575(10) -0.04229(16) 0.0310(4) Uani d . 1 . .
    H H10A 0.6761 0.4589 -0.0700 0.046 Uiso calc R 1 . .
    H H10B 0.8165 0.4719 -0.0872 0.046 Uiso calc R 1 . .
    H H10C 0.8065 0.4627 0.0346 0.046 Uiso calc R 1 . .
    C C11 0.87076(17) 0.33390(10) -0.11676(14) 0.0278(4) Uani d . 1 . .
    H H11A 0.9180 0.2865 -0.0852 0.042 Uiso calc R 1 . .
    H H11B 0.9344 0.3747 -0.1169 0.042 Uiso calc R 1 . .
    H H11C 0.8149 0.3238 -0.1926 0.042 Uiso calc R 1 . .
    C C12 0.64527(16) 0.11346(9) 0.08047(12) 0.0206(3) Uani d . 1 . .
    C C13 0.72488(19) -0.01248(9) 0.08182(16) 0.0311(4) Uani d . 1 . .
    H H13A 0.7386 -0.0189 0.1609 0.047 Uiso calc R 1 . .
    H H13B 0.7921 -0.0417 0.0612 0.047 Uiso calc R 1 . .
    H H13C 0.6373 -0.0318 0.0398 0.047 Uiso calc R 1 . .
    N N1 0.66103(13) 0.19181(7) 0.05907(10) 0.0190(3) Uani d . 1 . .
    O O1 0.80282(12) 0.18523(6) -0.04791(9) 0.0257(3) Uani d . 1 . .
    O O2 0.56148(13) 0.09040(7) 0.11740(12) 0.0348(3) Uani d . 1 . .
    O O3 0.73471(12) 0.06927(6) 0.05741(10) 0.0283(3) Uani d . 1 . .
    C C101 0.55129(15) 0.63537(9) 0.22129(12) 0.0192(3) Uani d . 1 . .
    C C102 0.59758(15) 0.70995(9) 0.18884(12) 0.0188(3) Uani d . 1 . .
    C C103 0.53483(15) 0.77124(9) 0.23422(12) 0.0187(3) Uani d . 1 . .
    C C104 0.46156(15) 0.73652(9) 0.29574(12) 0.0183(3) Uani d . 1 . .
    C C105 0.39122(16) 0.77967(10) 0.34964(13) 0.0244(4) Uani d . 1 . .
    H H105 0.3423 0.7553 0.3910 0.029 Uiso calc R 1 . .
    C C106 0.39472(17) 0.86001(10) 0.34109(14) 0.0284(4) Uani d . 1 . .
    H H106 0.3477 0.8910 0.3776 0.034 Uiso calc R 1 . .
    C C107 0.46537(17) 0.89569(10) 0.28054(15) 0.0280(4) Uani d . 1 . .
    H H107 0.4661 0.9506 0.2760 0.034 Uiso calc R 1 . .
    C C108 0.53524(16) 0.85203(9) 0.22639(13) 0.0242(4) Uani d . 1 . .
    H H108 0.5829 0.8769 0.1844 0.029 Uiso calc R 1 . .
    C C109 0.68425(15) 0.71469(9) 0.13126(12) 0.0207(3) Uani d . 1 . .
    C C110 0.72756(18) 0.79174(10) 0.09968(14) 0.0271(4) Uani d . 1 . .
    H H10D 0.6524 0.8177 0.0470 0.041 Uiso calc R 1 . .
    H H10E 0.7970 0.7837 0.0658 0.041 Uiso calc R 1 . .
    H H10F 0.7615 0.8240 0.1657 0.041 Uiso calc R 1 . .
    C C111 0.74405(17) 0.64527(10) 0.09521(14) 0.0265(4) Uani d . 1 . .
    H H11D 0.7586 0.6046 0.1513 0.040 Uiso calc R 1 . .
    H H11E 0.8284 0.6597 0.0856 0.040 Uiso calc R 1 . .
    H H11F 0.6843 0.6260 0.0251 0.040 Uiso calc R 1 . .
    C C112 0.41321(15) 0.60294(9) 0.34463(12) 0.0215(3) Uani d . 1 . .
    C C113 0.3678(2) 0.47259(11) 0.37137(16) 0.0412(5) Uani d . 1 . .
    H H13D 0.4060 0.4744 0.4518 0.062 Uiso calc R 1 . .
    H H13E 0.3808 0.4209 0.3449 0.062 Uiso calc R 1 . .
    H H13F 0.2733 0.4838 0.3505 0.062 Uiso calc R 1 . .
    N N101 0.47180(13) 0.65450(7) 0.28953(10) 0.0186(3) Uani d . 1 . .
    O O101 0.57215(12) 0.56998(6) 0.19634(10) 0.0278(3) Uani d . 1 . .
    O O102 0.35200(14) 0.62361(8) 0.40430(12) 0.0389(3) Uani d . 1 . .
    O O103 0.43198(14) 0.53012(7) 0.32211(11) 0.0358(3) Uani d . 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.2104(19) ?
    C1 N1 . 1.433(2) ?
    C1 C2 . 1.496(2) ?
    C2 C9 . 1.357(2) ?
    C2 C3 . 1.462(2) ?
    C3 C8 . 1.400(2) ?
    C3 C4 . 1.408(2) ?
    C4 C5 . 1.385(2) ?
    C4 N1 . 1.4283(19) ?
    C5 C6 . 1.395(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.388(2) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.387(2) ?
    C7 H7 . 0.9500 ?
    C8 H8 . 0.9500 ?
    C9 C11 . 1.501(2) ?
    C9 C10 . 1.505(2) ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 O2 . 1.204(2) ?
    C12 O3 . 1.327(2) ?
    C12 N1 . 1.400(2) ?
    C13 O3 . 1.4560(19) ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C101 O101 . 1.2124(19) ?
    C101 N101 . 1.434(2) ?
    C101 C102 . 1.484(2) ?
    C102 C109 . 1.355(2) ?
    C102 C103 . 1.466(2) ?
    C103 C108 . 1.398(2) ?
    C103 C104 . 1.406(2) ?
    C104 C105 . 1.386(2) ?
    C104 N101 . 1.424(2) ?
    C105 C106 . 1.392(2) ?
    C105 H105 . 0.9500 ?
    C106 C107 . 1.384(3) ?
    C106 H106 . 0.9500 ?
    C107 C108 . 1.389(2) ?
    C107 H107 . 0.9500 ?
    C108 H108 . 0.9500 ?
    C109 C111 . 1.497(2) ?
    C109 C110 . 1.504(2) ?
    C110 H10D . 0.9800 ?
    C110 H10E . 0.9800 ?
    C110 H10F . 0.9800 ?
    C111 H11D . 0.9800 ?
    C111 H11E . 0.9800 ?
    C111 H11F . 0.9800 ?
    C112 O102 . 1.204(2) ?
    C112 O103 . 1.319(2) ?
    C112 N101 . 1.399(2) ?
    C113 O103 . 1.458(2) ?
    C113 H13D . 0.9800 ?
    C113 H13E . 0.9800 ?
    C113 H13F . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 N1 . . 124.48(14) ?
    O1 C1 C2 . . 129.59(15) ?
    N1 C1 C2 . . 105.92(13) ?
    C9 C2 C3 . . 130.47(15) ?
    C9 C2 C1 . . 122.92(14) ?
    C3 C2 C1 . . 106.60(13) ?
    C8 C3 C4 . . 118.03(14) ?
    C8 C3 C2 . . 133.29(14) ?
    C4 C3 C2 . . 108.68(13) ?
    C5 C4 C3 . . 122.82(14) ?
    C5 C4 N1 . . 128.37(14) ?
    C3 C4 N1 . . 108.81(13) ?
    C4 C5 C6 . . 117.45(15) ?
    C4 C5 H5 . . 121.3 ?
    C6 C5 H5 . . 121.3 ?
    C7 C6 C5 . . 121.17(15) ?
    C7 C6 H6 . . 119.4 ?
    C5 C6 H6 . . 119.4 ?
    C8 C7 C6 . . 120.67(15) ?
    C8 C7 H7 . . 119.7 ?
    C6 C7 H7 . . 119.7 ?
    C7 C8 C3 . . 119.83(15) ?
    C7 C8 H8 . . 120.1 ?
    C3 C8 H8 . . 120.1 ?
    C2 C9 C11 . . 123.52(15) ?
    C2 C9 C10 . . 121.33(15) ?
    C11 C9 C10 . . 115.14(14) ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C9 C11 H11A . . 109.5 ?
    C9 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C9 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    O2 C12 O3 . . 125.04(15) ?
    O2 C12 N1 . . 123.08(15) ?
    O3 C12 N1 . . 111.86(14) ?
    O3 C13 H13A . . 109.5 ?
    O3 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    O3 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C12 N1 C4 . . 122.91(13) ?
    C12 N1 C1 . . 127.14(13) ?
    C4 N1 C1 . . 109.94(12) ?
    C12 O3 C13 . . 113.82(13) ?
    O101 C101 N101 . . 124.55(14) ?
    O101 C101 C102 . . 128.97(15) ?
    N101 C101 C102 . . 106.47(13) ?
    C109 C102 C103 . . 130.33(15) ?
    C109 C102 C101 . . 123.31(15) ?
    C103 C102 C101 . . 106.32(13) ?
    C108 C103 C104 . . 118.68(15) ?
    C108 C103 C102 . . 132.78(15) ?
    C104 C103 C102 . . 108.54(14) ?
    C105 C104 C103 . . 122.24(15) ?
    C105 C104 N101 . . 128.70(15) ?
    C103 C104 N101 . . 109.05(13) ?
    C104 C105 C106 . . 117.65(16) ?
    C104 C105 H105 . . 121.2 ?
    C106 C105 H105 . . 121.2 ?
    C107 C106 C105 . . 121.32(16) ?
    C107 C106 H106 . . 119.3 ?
    C105 C106 H106 . . 119.3 ?
    C106 C107 C108 . . 120.69(16) ?
    C106 C107 H107 . . 119.7 ?
    C108 C107 H107 . . 119.7 ?
    C107 C108 C103 . . 119.42(16) ?
    C107 C108 H108 . . 120.3 ?
    C103 C108 H108 . . 120.3 ?
    C102 C109 C111 . . 123.36(15) ?
    C102 C109 C110 . . 121.32(15) ?
    C111 C109 C110 . . 115.32(14) ?
    C109 C110 H10D . . 109.5 ?
    C109 C110 H10E . . 109.5 ?
    H10D C110 H10E . . 109.5 ?
    C109 C110 H10F . . 109.5 ?
    H10D C110 H10F . . 109.5 ?
    H10E C110 H10F . . 109.5 ?
    C109 C111 H11D . . 109.5 ?
    C109 C111 H11E . . 109.5 ?
    H11D C111 H11E . . 109.5 ?
    C109 C111 H11F . . 109.5 ?
    H11D C111 H11F . . 109.5 ?
    H11E C111 H11F . . 109.5 ?
    O102 C112 O103 . . 124.80(15) ?
    O102 C112 N101 . . 123.25(15) ?
    O103 C112 N101 . . 111.94(14) ?
    O103 C113 H13D . . 109.5 ?
    O103 C113 H13E . . 109.5 ?
    H13D C113 H13E . . 109.5 ?
    O103 C113 H13F . . 109.5 ?
    H13D C113 H13F . . 109.5 ?
    H13E C113 H13F . . 109.5 ?
    C112 N101 C104 . . 123.36(13) ?
    C112 N101 C101 . . 127.16(13) ?
    C104 N101 C101 . . 109.47(12) ?
    C112 O103 C113 . . 115.50(14) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C9 . . . . 1.4(3) ?
    N1 C1 C2 C9 . . . . -177.93(13) ?
    O1 C1 C2 C3 . . . . -179.77(15) ?
    N1 C1 C2 C3 . . . . 0.90(15) ?
    C9 C2 C3 C8 . . . . -3.5(3) ?
    C1 C2 C3 C8 . . . . 177.82(16) ?
    C9 C2 C3 C4 . . . . 176.70(15) ?
    C1 C2 C3 C4 . . . . -2.02(16) ?
    C8 C3 C4 C5 . . . . 1.8(2) ?
    C2 C3 C4 C5 . . . . -178.29(13) ?
    C8 C3 C4 N1 . . . . -177.50(13) ?
    C2 C3 C4 N1 . . . . 2.36(16) ?
    C3 C4 C5 C6 . . . . -1.5(2) ?
    N1 C4 C5 C6 . . . . 177.76(14) ?
    C4 C5 C6 C7 . . . . -0.1(2) ?
    C5 C6 C7 C8 . . . . 1.2(2) ?
    C6 C7 C8 C3 . . . . -0.8(2) ?
    C4 C3 C8 C7 . . . . -0.7(2) ?
    C2 C3 C8 C7 . . . . 179.51(15) ?
    C3 C2 C9 C11 . . . . -178.52(14) ?
    C1 C2 C9 C11 . . . . 0.0(2) ?
    C3 C2 C9 C10 . . . . 1.0(3) ?
    C1 C2 C9 C10 . . . . 179.52(14) ?
    O2 C12 N1 C4 . . . . 13.9(2) ?
    O3 C12 N1 C4 . . . . -164.77(13) ?
    O2 C12 N1 C1 . . . . -167.99(15) ?
    O3 C12 N1 C1 . . . . 13.3(2) ?
    C5 C4 N1 C12 . . . . -2.7(2) ?
    C3 C4 N1 C12 . . . . 176.59(13) ?
    C5 C4 N1 C1 . . . . 178.90(14) ?
    C3 C4 N1 C1 . . . . -1.80(16) ?
    O1 C1 N1 C12 . . . . 2.8(2) ?
    C2 C1 N1 C12 . . . . -177.79(13) ?
    O1 C1 N1 C4 . . . . -178.85(14) ?
    C2 C1 N1 C4 . . . . 0.51(15) ?
    O2 C12 O3 C13 . . . . -0.6(2) ?
    N1 C12 O3 C13 . . . . 178.09(13) ?
    O101 C101 C102 C109 . . . . -6.4(3) ?
    N101 C101 C102 C109 . . . . 174.45(13) ?
    O101 C101 C102 C103 . . . . 175.36(15) ?
    N101 C101 C102 C103 . . . . -3.78(15) ?
    C109 C102 C103 C108 . . . . 5.7(3) ?
    C101 C102 C103 C108 . . . . -176.29(16) ?
    C109 C102 C103 C104 . . . . -174.79(15) ?
    C101 C102 C103 C104 . . . . 3.27(16) ?
    C108 C103 C104 C105 . . . . -0.7(2) ?
    C102 C103 C104 C105 . . . . 179.63(14) ?
    C108 C103 C104 N101 . . . . 178.14(13) ?
    C102 C103 C104 N101 . . . . -1.49(16) ?
    C103 C104 C105 C106 . . . . 0.1(2) ?
    N101 C104 C105 C106 . . . . -178.53(14) ?
    C104 C105 C106 C107 . . . . 0.3(2) ?
    C105 C106 C107 C108 . . . . -0.1(3) ?
    C106 C107 C108 C103 . . . . -0.6(2) ?
    C104 C103 C108 C107 . . . . 1.0(2) ?
    C102 C103 C108 C107 . . . . -179.52(15) ?
    C103 C102 C109 C111 . . . . 177.02(14) ?
    C101 C102 C109 C111 . . . . -0.7(2) ?
    C103 C102 C109 C110 . . . . -2.6(2) ?
    C101 C102 C109 C110 . . . . 179.62(14) ?
    O102 C112 N101 C104 . . . . -2.0(2) ?
    O103 C112 N101 C104 . . . . 177.23(13) ?
    O102 C112 N101 C101 . . . . 176.86(15) ?
    O103 C112 N101 C101 . . . . -3.9(2) ?
    C105 C104 N101 C112 . . . . -3.2(2) ?
    C103 C104 N101 C112 . . . . 178.06(13) ?
    C105 C104 N101 C101 . . . . 177.81(15) ?
    C103 C104 N101 C101 . . . . -0.98(16) ?
    O101 C101 N101 C112 . . . . 4.8(2) ?
    C102 C101 N101 C112 . . . . -176.01(13) ?
    O101 C101 N101 C104 . . . . -176.20(14) ?
    C102 C101 N101 C104 . . . . 2.98(16) ?
    O102 C112 O103 C113 . . . . 2.5(3) ?
    N101 C112 O103 C113 . . . . -176.69(15) ?
data_4c
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
3-cyclohexylidene-1H-indol-2(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H15 N O'
_chemical_formula_sum     'C14 H15 N O'
_chemical_formula_iupac     'C14 H15 N O'
_chemical_formula_weight     213.27
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     5.37320(10)
_cell_length_b     13.4962(4)
_cell_length_c     15.8088(5)
_cell_angle_alpha     95.3890(10)
_cell_angle_beta     98.498(2)
_cell_angle_gamma     101.201(2)
_cell_volume     1103.32(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     12338
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     'light brown'
_exptl_crystal_size_max     0.85
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.284
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     456
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min     0.9346
_exptl_absorpt_correction_T_max     0.9952
_exptl_special_details
;
SADABS was used to perform the Absorption correction. Parameter
refinement on 15813 reflections reduced R(int) from 0.1450 to 0.0586.
Ratio of minimum to maximum apparent transmission: 0.870535. The given Tmin
and Tmax were generated using the SHELX SIZE command.
The crystals were long needles which shattered when cut. Thus it was necessary
to mount a much longer crystal than would be ideal.
NMR spectra were measured on a Jeol EX270 spectrometer at 270 MHz (¹H) and 68
MHz (¹³C) in CDCl₃. High-resolution mass spectra were performed by the
EPSRC facility, Swansea University, Wales. ¹H NMR (270 MHz, CDCl₃, δ,
p.p.m.): 7.72 (1H, s), 7.61 (1H, d, J = 7.70 Hz), 7.19--7.13 (1H, m),
7.01--6.95 (1H, m), 6.82 (1H, d, J = 7.70 Hz), 3.34 (2H, t, J = 6.60 Hz, J =
5.50 Hz), 2.86 (2H, t, J = 6.60 Hz, J = 5.87 Hz), 1.84--1.69 (6H, m).
¹³C NMR (75 MHz, CDCl₃, δ, p.p.m.): DEPT: 127.5, 123.7, 121.5, 109.3 (CH),
33.1, 30.0, 28.1, 27.8, 25.7 (CH₂).
IR (KBr, ν, cm⁻¹): 3170, 2936, 1684, 1351, 1221, 747.
HRMS: m/z calculated for C₁₄H₁₆NO(MH+) 214.1226, found
214.1230.
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     '10cm confocal mirrors'
_diffrn_measurement_device_type
                               'Bruker Nonius APEXII CCD camera on κ-goniostat'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     '4096x4096pixels / 62x62mm'
_diffrn_reflns_number     18503
_diffrn_reflns_av_R_equivalents     0.0589
_diffrn_reflns_av_sigmaI/netI     0.0577
_diffrn_reflns_theta_min     3.10
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     4997
_reflns_number_gt     3778
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0940
_refine_ls_R_factor_gt     0.0660
_refine_ls_wR_factor_gt     0.1199
_refine_ls_wR_factor_ref     0.1347
_refine_ls_goodness_of_fit_ref     1.072
_refine_ls_restrained_S_all     1.072
_refine_ls_number_reflns     4997
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0002P)²+1.4948P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.328
_refine_diff_density_min     -0.235
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Version 2.01; Farrugia, 1997) and
Mercury (Version 1.4.2; Macrae et al., 2006)
;
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 1.2267(4) 0.49598(18) 0.07719(13) 0.0215(5) Uani d . 1 . .
    C C2 1.0170(4) 0.46698(17) 0.12946(13) 0.0197(4) Uani d . 1 . .
    C C3 0.9590(4) 0.35410(17) 0.11870(14) 0.0215(5) Uani d . 1 . .
    C C4 1.1289(4) 0.32256(17) 0.06723(14) 0.0219(5) Uani d . 1 . .
    C C5 1.1335(5) 0.22196(18) 0.04454(15) 0.0265(5) Uani d . 1 . .
    H H5 1.2530 0.2034 0.0105 0.032 Uiso calc R 1 . .
    C C6 0.9566(5) 0.14822(18) 0.07327(15) 0.0273(5) Uani d . 1 . .
    H H6 0.9559 0.0782 0.0592 0.033 Uiso calc R 1 . .
    C C7 0.7826(5) 0.17608(18) 0.12201(15) 0.0274(5) Uani d . 1 . .
    H H7 0.6623 0.1249 0.1407 0.033 Uiso calc R 1 . .
    C C8 0.7811(4) 0.27834(18) 0.14421(15) 0.0256(5) Uani d . 1 . .
    H H8 0.6581 0.2964 0.1769 0.031 Uiso calc R 1 . .
    C C9 0.9254(4) 0.53507(17) 0.17809(14) 0.0218(5) Uani d . 1 . .
    C C10 0.7413(5) 0.50503(19) 0.23890(16) 0.0296(5) Uani d . 1 . .
    H H10A 0.6947 0.4299 0.2350 0.035 Uiso calc R 1 . .
    H H10B 0.5817 0.5301 0.2224 0.035 Uiso calc R 1 . .
    C C11 0.8652(5) 0.55019(18) 0.33175(15) 0.0264(5) Uani d . 1 . .
    H H11A 0.7406 0.5318 0.3709 0.032 Uiso calc R 1 . .
    H H11B 1.0173 0.5210 0.3496 0.032 Uiso calc R 1 . .
    C C12 0.9474(4) 0.66549(17) 0.33919(15) 0.0242(5) Uani d . 1 . .
    H H12A 1.0360 0.6926 0.3987 0.029 Uiso calc R 1 . .
    H H12B 0.7933 0.6953 0.3272 0.029 Uiso calc R 1 . .
    C C13 1.1275(4) 0.69620(17) 0.27574(15) 0.0243(5) Uani d . 1 . .
    H H13A 1.2907 0.6738 0.2924 0.029 Uiso calc R 1 . .
    H H13B 1.1681 0.7713 0.2785 0.029 Uiso calc R 1 . .
    C C14 1.0064(4) 0.64885(17) 0.18258(15) 0.0241(5) Uani d . 1 . .
    H H14A 0.8548 0.6776 0.1631 0.029 Uiso calc R 1 . .
    H H14B 1.1329 0.6658 0.1438 0.029 Uiso calc R 1 . .
    N N1 1.2855(4) 0.40804(14) 0.04460(12) 0.0234(4) Uani d . 1 . .
    H H1 1.4069 0.4053 0.0132 0.028 Uiso calc R 1 . .
    O O1 1.3379(3) 0.58122(12) 0.06518(10) 0.0255(4) Uani d . 1 . .
    C C101 0.7052(4) 0.05891(16) 0.44320(15) 0.0208(5) Uani d . 1 . .
    C C102 0.4930(4) 0.08886(16) 0.38401(14) 0.0202(5) Uani d . 1 . .
    C C103 0.4658(4) 0.02215(16) 0.30140(14) 0.0211(5) Uani d . 1 . .
    C C104 0.6567(4) -0.03585(16) 0.31196(15) 0.0220(5) Uani d . 1 . .
    C C105 0.6866(5) -0.10715(18) 0.24781(16) 0.0271(5) Uani d . 1 . .
    H H105 0.8198 -0.1441 0.2564 0.033 Uiso calc R 1 . .
    C C106 0.5157(5) -0.12313(18) 0.17030(16) 0.0295(5) Uani d . 1 . .
    H H106 0.5331 -0.1710 0.1247 0.035 Uiso calc R 1 . .
    C C107 0.3196(5) -0.06953(18) 0.15912(15) 0.0281(5) Uani d . 1 . .
    H H107 0.2018 -0.0823 0.1063 0.034 Uiso calc R 1 . .
    C C108 0.2931(4) 0.00282(17) 0.22444(15) 0.0246(5) Uani d . 1 . .
    H H108 0.1575 0.0386 0.2162 0.030 Uiso calc R 1 . .
    C C109 0.3749(4) 0.16534(16) 0.40503(14) 0.0211(5) Uani d . 1 . .
    C C110 0.1966(5) 0.20541(17) 0.33968(15) 0.0269(5) Uani d . 1 . .
    H H11C 0.0179 0.1862 0.3507 0.032 Uiso calc R 1 . .
    H H11D 0.2016 0.1738 0.2810 0.032 Uiso calc R 1 . .
    C C111 0.2739(5) 0.32120(17) 0.34438(15) 0.0269(5) Uani d . 1 . .
    H H11E 0.4421 0.3396 0.3250 0.032 Uiso calc R 1 . .
    H H11F 0.1448 0.3456 0.3048 0.032 Uiso calc R 1 . .
    C C112 0.2938(5) 0.37387(17) 0.43536(15) 0.0263(5) Uani d . 1 . .
    H H11G 0.1226 0.3604 0.4532 0.032 Uiso calc R 1 . .
    H H11H 0.3508 0.4484 0.4365 0.032 Uiso calc R 1 . .
    C C113 0.4856(4) 0.33473(17) 0.49802(15) 0.0239(5) Uani d . 1 . .
    H H11I 0.4918 0.3673 0.5573 0.029 Uiso calc R 1 . .
    H H11J 0.6596 0.3534 0.4829 0.029 Uiso calc R 1 . .
    C C114 0.4086(4) 0.21904(17) 0.49482(14) 0.0225(5) Uani d . 1 . .
    H H11K 0.5428 0.1951 0.5326 0.027 Uiso calc R 1 . .
    H H11L 0.2454 0.2014 0.5174 0.027 Uiso calc R 1 . .
    N N101 0.7970(3) -0.01058(14) 0.39543(12) 0.0236(4) Uani d . 1 . .
    H H101 0.9293 -0.0365 0.4148 0.028 Uiso calc R 1 . .
    O O101 0.7941(3) 0.09076(12) 0.51969(10) 0.0255(4) Uani d . 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.234(3) ?
    C1 N1 . 1.361(3) ?
    C1 C2 . 1.507(3) ?
    C2 C9 . 1.354(3) ?
    C2 C3 . 1.483(3) ?
    C3 C8 . 1.390(3) ?
    C3 C4 . 1.408(3) ?
    C4 C5 . 1.377(3) ?
    C4 N1 . 1.399(3) ?
    C5 C6 . 1.395(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.380(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.393(3) ?
    C7 H7 . 0.9500 ?
    C8 H8 . 0.9500 ?
    C9 C14 . 1.504(3) ?
    C9 C10 . 1.505(3) ?
    C10 C11 . 1.535(3) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C12 . 1.521(3) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.524(3) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.543(3) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    N1 H1 . 0.8800 ?
    C101 O101 . 1.236(3) ?
    C101 N101 . 1.360(3) ?
    C101 C102 . 1.508(3) ?
    C102 C109 . 1.353(3) ?
    C102 C103 . 1.486(3) ?
    C103 C108 . 1.386(3) ?
    C103 C104 . 1.407(3) ?
    C104 C105 . 1.381(3) ?
    C104 N101 . 1.396(3) ?
    C105 C106 . 1.390(3) ?
    C105 H105 . 0.9500 ?
    C106 C107 . 1.389(3) ?
    C106 H106 . 0.9500 ?
    C107 C108 . 1.396(3) ?
    C107 H107 . 0.9500 ?
    C108 H108 . 0.9500 ?
    C109 C114 . 1.501(3) ?
    C109 C110 . 1.514(3) ?
    C110 C111 . 1.529(3) ?
    C110 H11C . 0.9900 ?
    C110 H11D . 0.9900 ?
    C111 C112 . 1.523(3) ?
    C111 H11E . 0.9900 ?
    C111 H11F . 0.9900 ?
    C112 C113 . 1.527(3) ?
    C112 H11G . 0.9900 ?
    C112 H11H . 0.9900 ?
    C113 C114 . 1.530(3) ?
    C113 H11I . 0.9900 ?
    C113 H11J . 0.9900 ?
    C114 H11K . 0.9900 ?
    C114 H11L . 0.9900 ?
    N101 H101 . 0.8800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 N1 . . 123.3(2) ?
    O1 C1 C2 . . 129.5(2) ?
    N1 C1 C2 . . 107.13(18) ?
    C9 C2 C3 . . 131.1(2) ?
    C9 C2 C1 . . 124.0(2) ?
    C3 C2 C1 . . 104.83(18) ?
    C8 C3 C4 . . 117.2(2) ?
    C8 C3 C2 . . 135.8(2) ?
    C4 C3 C2 . . 106.95(19) ?
    C5 C4 N1 . . 127.1(2) ?
    C5 C4 C3 . . 123.4(2) ?
    N1 C4 C3 . . 109.48(19) ?
    C4 C5 C6 . . 117.6(2) ?
    C4 C5 H5 . . 121.2 ?
    C6 C5 H5 . . 121.2 ?
    C7 C6 C5 . . 120.6(2) ?
    C7 C6 H6 . . 119.7 ?
    C5 C6 H6 . . 119.7 ?
    C6 C7 C8 . . 120.8(2) ?
    C6 C7 H7 . . 119.6 ?
    C8 C7 H7 . . 119.6 ?
    C3 C8 C7 . . 120.3(2) ?
    C3 C8 H8 . . 119.9 ?
    C7 C8 H8 . . 119.9 ?
    C2 C9 C14 . . 124.7(2) ?
    C2 C9 C10 . . 123.3(2) ?
    C14 C9 C10 . . 111.85(19) ?
    C9 C10 C11 . . 110.14(19) ?
    C9 C10 H10A . . 109.6 ?
    C11 C10 H10A . . 109.6 ?
    C9 C10 H10B . . 109.6 ?
    C11 C10 H10B . . 109.6 ?
    H10A C10 H10B . . 108.1 ?
    C12 C11 C10 . . 110.90(19) ?
    C12 C11 H11A . . 109.5 ?
    C10 C11 H11A . . 109.5 ?
    C12 C11 H11B . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 108.0 ?
    C11 C12 C13 . . 110.63(19) ?
    C11 C12 H12A . . 109.5 ?
    C13 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    C13 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 108.1 ?
    C12 C13 C14 . . 111.61(19) ?
    C12 C13 H13A . . 109.3 ?
    C14 C13 H13A . . 109.3 ?
    C12 C13 H13B . . 109.3 ?
    C14 C13 H13B . . 109.3 ?
    H13A C13 H13B . . 108.0 ?
    C9 C14 C13 . . 110.24(18) ?
    C9 C14 H14A . . 109.6 ?
    C13 C14 H14A . . 109.6 ?
    C9 C14 H14B . . 109.6 ?
    C13 C14 H14B . . 109.6 ?
    H14A C14 H14B . . 108.1 ?
    C1 N1 C4 . . 111.54(18) ?
    C1 N1 H1 . . 124.2 ?
    C4 N1 H1 . . 124.2 ?
    O101 C101 N101 . . 123.7(2) ?
    O101 C101 C102 . . 129.4(2) ?
    N101 C101 C102 . . 106.85(19) ?
    C109 C102 C103 . . 130.7(2) ?
    C109 C102 C101 . . 124.5(2) ?
    C103 C102 C101 . . 104.66(18) ?
    C108 C103 C104 . . 118.1(2) ?
    C108 C103 C102 . . 134.7(2) ?
    C104 C103 C102 . . 107.06(19) ?
    C105 C104 N101 . . 127.8(2) ?
    C105 C104 C103 . . 122.9(2) ?
    N101 C104 C103 . . 109.2(2) ?
    C104 C105 C106 . . 117.9(2) ?
    C104 C105 H105 . . 121.1 ?
    C106 C105 H105 . . 121.1 ?
    C107 C106 C105 . . 120.4(2) ?
    C107 C106 H106 . . 119.8 ?
    C105 C106 H106 . . 119.8 ?
    C106 C107 C108 . . 120.9(2) ?
    C106 C107 H107 . . 119.5 ?
    C108 C107 H107 . . 119.5 ?
    C103 C108 C107 . . 119.7(2) ?
    C103 C108 H108 . . 120.2 ?
    C107 C108 H108 . . 120.2 ?
    C102 C109 C114 . . 123.5(2) ?
    C102 C109 C110 . . 123.0(2) ?
    C114 C109 C110 . . 113.48(19) ?
    C109 C110 C111 . . 111.26(19) ?
    C109 C110 H11C . . 109.4 ?
    C111 C110 H11C . . 109.4 ?
    C109 C110 H11D . . 109.4 ?
    C111 C110 H11D . . 109.4 ?
    H11C C110 H11D . . 108.0 ?
    C112 C111 C110 . . 111.86(19) ?
    C112 C111 H11E . . 109.2 ?
    C110 C111 H11E . . 109.2 ?
    C112 C111 H11F . . 109.2 ?
    C110 C111 H11F . . 109.2 ?
    H11E C111 H11F . . 107.9 ?
    C111 C112 C113 . . 110.08(19) ?
    C111 C112 H11G . . 109.6 ?
    C113 C112 H11G . . 109.6 ?
    C111 C112 H11H . . 109.6 ?
    C113 C112 H11H . . 109.6 ?
    H11G C112 H11H . . 108.2 ?
    C112 C113 C114 . . 110.81(19) ?
    C112 C113 H11I . . 109.5 ?
    C114 C113 H11I . . 109.5 ?
    C112 C113 H11J . . 109.5 ?
    C114 C113 H11J . . 109.5 ?
    H11I C113 H11J . . 108.1 ?
    C109 C114 C113 . . 112.15(18) ?
    C109 C114 H11K . . 109.2 ?
    C113 C114 H11K . . 109.2 ?
    C109 C114 H11L . . 109.2 ?
    C113 C114 H11L . . 109.2 ?
    H11K C114 H11L . . 107.9 ?
    C101 N101 C104 . . 111.99(18) ?
    C101 N101 H101 . . 124.0 ?
    C104 N101 H101 . . 124.0 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C9 . . . . -4.4(4) ?
    N1 C1 C2 C9 . . . . 173.8(2) ?
    O1 C1 C2 C3 . . . . 179.2(2) ?
    N1 C1 C2 C3 . . . . -2.6(2) ?
    C9 C2 C3 C8 . . . . 8.3(4) ?
    C1 C2 C3 C8 . . . . -175.7(2) ?
    C9 C2 C3 C4 . . . . -174.0(2) ?
    C1 C2 C3 C4 . . . . 2.0(2) ?
    C8 C3 C4 C5 . . . . -2.7(3) ?
    C2 C3 C4 C5 . . . . 179.1(2) ?
    C8 C3 C4 N1 . . . . 177.43(19) ?
    C2 C3 C4 N1 . . . . -0.7(2) ?
    N1 C4 C5 C6 . . . . -179.1(2) ?
    C3 C4 C5 C6 . . . . 1.1(3) ?
    C4 C5 C6 C7 . . . . 0.6(3) ?
    C5 C6 C7 C8 . . . . -0.6(4) ?
    C4 C3 C8 C7 . . . . 2.7(3) ?
    C2 C3 C8 C7 . . . . -179.8(2) ?
    C6 C7 C8 C3 . . . . -1.1(4) ?
    C3 C2 C9 C14 . . . . 179.5(2) ?
    C1 C2 C9 C14 . . . . 4.1(3) ?
    C3 C2 C9 C10 . . . . 3.6(4) ?
    C1 C2 C9 C10 . . . . -171.7(2) ?
    C2 C9 C10 C11 . . . . 118.1(2) ?
    C14 C9 C10 C11 . . . . -58.3(3) ?
    C9 C10 C11 C12 . . . . 57.3(3) ?
    C10 C11 C12 C13 . . . . -55.9(2) ?
    C11 C12 C13 C14 . . . . 54.8(2) ?
    C2 C9 C14 C13 . . . . -119.5(2) ?
    C10 C9 C14 C13 . . . . 56.8(2) ?
    C12 C13 C14 C9 . . . . -54.9(2) ?
    O1 C1 N1 C4 . . . . -179.4(2) ?
    C2 C1 N1 C4 . . . . 2.2(2) ?
    C5 C4 N1 C1 . . . . 179.2(2) ?
    C3 C4 N1 C1 . . . . -1.0(2) ?
    O101 C101 C102 C109 . . . . 5.8(4) ?
    N101 C101 C102 C109 . . . . -171.8(2) ?
    O101 C101 C102 C103 . . . . -178.0(2) ?
    N101 C101 C102 C103 . . . . 4.5(2) ?
    C109 C102 C103 C108 . . . . -12.0(4) ?
    C101 C102 C103 C108 . . . . 172.1(2) ?
    C109 C102 C103 C104 . . . . 172.8(2) ?
    C101 C102 C103 C104 . . . . -3.1(2) ?
    C108 C103 C104 C105 . . . . 3.2(3) ?
    C102 C103 C104 C105 . . . . 179.4(2) ?
    C108 C103 C104 N101 . . . . -175.44(19) ?
    C102 C103 C104 N101 . . . . 0.8(2) ?
    N101 C104 C105 C106 . . . . 177.0(2) ?
    C103 C104 C105 C106 . . . . -1.4(3) ?
    C104 C105 C106 C107 . . . . -0.9(3) ?
    C105 C106 C107 C108 . . . . 1.4(4) ?
    C104 C103 C108 C107 . . . . -2.7(3) ?
    C102 C103 C108 C107 . . . . -177.6(2) ?
    C106 C107 C108 C103 . . . . 0.5(3) ?
    C103 C102 C109 C114 . . . . 174.2(2) ?
    C101 C102 C109 C114 . . . . -10.6(3) ?
    C103 C102 C109 C110 . . . . -6.2(4) ?
    C101 C102 C109 C110 . . . . 169.0(2) ?
    C102 C109 C110 C111 . . . . -128.4(2) ?
    C114 C109 C110 C111 . . . . 51.2(3) ?
    C109 C110 C111 C112 . . . . -53.8(3) ?
    C110 C111 C112 C113 . . . . 57.1(3) ?
    C111 C112 C113 C114 . . . . -56.8(2) ?
    C102 C109 C114 C113 . . . . 127.6(2) ?
    C110 C109 C114 C113 . . . . -52.0(2) ?
    C112 C113 C114 C109 . . . . 54.5(2) ?
    O101 C101 N101 C104 . . . . 178.0(2) ?
    C102 C101 N101 C104 . . . . -4.3(2) ?
    C105 C104 N101 C101 . . . . -176.3(2) ?
    C103 C104 N101 C101 . . . . 2.3(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 O1 2_865 0.88 1.97 2.846(2) 170.5 no
    N101 H101 O101 2_756 0.88 1.98 2.850(2) 169.0 no
data_5
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
spiro[1,3-dioxane-2,3'-indolin]-2'-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H11 N O3'
_chemical_formula_sum     'C11 H11 N O3'
_chemical_formula_iupac     'C11 H11 N O3'
_chemical_formula_weight     205.21
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.5406(2)
_cell_length_b     8.4295(2)
_cell_length_c     12.4103(3)
_cell_angle_alpha     90.00
_cell_angle_beta     101.956(2)
_cell_angle_gamma     90.00
_cell_volume     976.42(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6650
_cell_measurement_theta_min     2.91
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     120(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.36
_exptl_crystal_density_diffrn     1.396
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     432
_exptl_absorpt_coefficient_mu     0.103
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min     0.9505
_exptl_absorpt_correction_T_max     0.9640
_exptl_special_details
;
SADABS was used to perform the Absorption correction. Estimated minimum
and maximum transmission from SADABS: 0.6701 and 0.7456. The given Tmin
and Tmax were generated using the SHELX SIZE command.
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type
                                'Bruker Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     12504
_diffrn_reflns_av_R_equivalents     0.0317
_diffrn_reflns_av_sigmaI/netI     0.0247
_diffrn_reflns_theta_min     2.94
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2227
_reflns_number_gt     1885
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0480
_refine_ls_R_factor_gt     0.0386
_refine_ls_wR_factor_gt     0.0967
_refine_ls_wR_factor_ref     0.1032
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     2227
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0531P)²+0.3966P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.253
_refine_diff_density_min     -0.262
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_structure_solution     'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Version 2.01; Farrugia, 1997) and
Mercury (Version 1.4.2; Macrae et al., 2006)
;
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.82232(13) 0.13311(15) 0.46137(10) 0.0173(3) Uani d . 1 . .
    C C2 0.70894(13) 0.27006(14) 0.43910(9) 0.0150(3) Uani d . 1 . .
    C C3 0.77938(13) 0.39587(14) 0.51817(9) 0.0156(3) Uani d . 1 . .
    C C4 0.91344(13) 0.34128(14) 0.57220(9) 0.0159(3) Uani d . 1 . .
    C C5 1.00677(13) 0.43401(15) 0.64610(10) 0.0190(3) Uani d . 1 . .
    H H5 1.0980 0.3954 0.6823 0.023 Uiso calc R 1 . .
    C C6 0.96138(14) 0.58679(16) 0.66535(10) 0.0213(3) Uani d . 1 . .
    H H6 1.0231 0.6540 0.7154 0.026 Uiso calc R 1 . .
    C C7 0.82781(14) 0.64256(16) 0.61273(11) 0.0216(3) Uani d . 1 . .
    H H7 0.7993 0.7469 0.6277 0.026 Uiso calc R 1 . .
    C C8 0.73439(14) 0.54706(15) 0.53783(10) 0.0189(3) Uani d . 1 . .
    H H8 0.6430 0.5850 0.5017 0.023 Uiso calc R 1 . .
    C C9 0.49725(14) 0.11220(16) 0.38562(10) 0.0209(3) Uani d . 1 . .
    H H9A 0.4031 0.0910 0.4043 0.025 Uiso calc R 1 . .
    H H9B 0.5502 0.0107 0.3894 0.025 Uiso calc R 1 . .
    C C10 0.47547(14) 0.17928(17) 0.27001(10) 0.0233(3) Uani d . 1 . .
    H H10A 0.4273 0.0999 0.2160 0.028 Uiso calc R 1 . .
    H H10B 0.4143 0.2751 0.2637 0.028 Uiso calc R 1 . .
    C C11 0.62060(14) 0.22133(16) 0.24641(10) 0.0215(3) Uani d . 1 . .
    H H11A 0.6781 0.1238 0.2455 0.026 Uiso calc R 1 . .
    H H11B 0.6082 0.2726 0.1733 0.026 Uiso calc R 1 . .
    N N1 0.93439(11) 0.18507(13) 0.53853(8) 0.0180(2) Uani d . 1 . .
    H H1 1.0112 0.1281 0.5646 0.022 Uiso calc R 1 . .
    O O1 0.81223(10) 0.00212(11) 0.41678(8) 0.0250(2) Uani d . 1 . .
    O O2 0.57725(9) 0.22394(11) 0.46401(7) 0.0179(2) Uani d . 1 . .
    O O3 0.69446(9) 0.32872(10) 0.33099(6) 0.0176(2) Uani d . 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.2298(15) ?
    C1 N1 . 1.3519(16) ?
    C1 C2 . 1.5670(16) ?
    C2 O2 . 1.4093(15) ?
    C2 O3 . 1.4096(14) ?
    C2 C3 . 1.5053(16) ?
    C3 C8 . 1.3825(17) ?
    C3 C4 . 1.3935(17) ?
    C4 C5 . 1.3807(17) ?
    C4 N1 . 1.4082(16) ?
    C5 C6 . 1.3950(18) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.3880(18) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.4012(18) ?
    C7 H7 . 0.9500 ?
    C8 H8 . 0.9500 ?
    C9 O2 . 1.4521(14) ?
    C9 C10 . 1.5158(18) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.5155(19) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 O3 . 1.4530(14) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    N1 H1 . 0.8800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 N1 . . 125.89(11) ?
    O1 C1 C2 . . 126.53(11) ?
    N1 C1 C2 . . 107.58(10) ?
    O2 C2 O3 . . 112.93(9) ?
    O2 C2 C3 . . 110.45(9) ?
    O3 C2 C3 . . 108.41(9) ?
    O2 C2 C1 . . 111.85(9) ?
    O3 C2 C1 . . 110.75(9) ?
    C3 C2 C1 . . 101.85(9) ?
    C8 C3 C4 . . 120.47(11) ?
    C8 C3 C2 . . 130.65(11) ?
    C4 C3 C2 . . 108.81(10) ?
    C5 C4 C3 . . 122.27(11) ?
    C5 C4 N1 . . 127.94(11) ?
    C3 C4 N1 . . 109.79(10) ?
    C4 C5 C6 . . 117.13(11) ?
    C4 C5 H5 . . 121.4 ?
    C6 C5 H5 . . 121.4 ?
    C7 C6 C5 . . 121.29(12) ?
    C7 C6 H6 . . 119.4 ?
    C5 C6 H6 . . 119.4 ?
    C6 C7 C8 . . 120.89(12) ?
    C6 C7 H7 . . 119.6 ?
    C8 C7 H7 . . 119.6 ?
    C3 C8 C7 . . 117.94(11) ?
    C3 C8 H8 . . 121.0 ?
    C7 C8 H8 . . 121.0 ?
    O2 C9 C10 . . 110.01(10) ?
    O2 C9 H9A . . 109.7 ?
    C10 C9 H9A . . 109.7 ?
    O2 C9 H9B . . 109.7 ?
    C10 C9 H9B . . 109.7 ?
    H9A C9 H9B . . 108.2 ?
    C11 C10 C9 . . 108.58(10) ?
    C11 C10 H10A . . 110.0 ?
    C9 C10 H10A . . 110.0 ?
    C11 C10 H10B . . 110.0 ?
    C9 C10 H10B . . 110.0 ?
    H10A C10 H10B . . 108.4 ?
    O3 C11 C10 . . 109.39(10) ?
    O3 C11 H11A . . 109.8 ?
    C10 C11 H11A . . 109.8 ?
    O3 C11 H11B . . 109.8 ?
    C10 C11 H11B . . 109.8 ?
    H11A C11 H11B . . 108.2 ?
    C1 N1 C4 . . 111.91(10) ?
    C1 N1 H1 . . 124.0 ?
    C4 N1 H1 . . 124.0 ?
    C2 O2 C9 . . 113.62(9) ?
    C2 O3 C11 . . 113.97(9) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 O2 . . . . 61.07(16) ?
    N1 C1 C2 O2 . . . . -119.21(11) ?
    O1 C1 C2 O3 . . . . -65.86(16) ?
    N1 C1 C2 O3 . . . . 113.87(11) ?
    O1 C1 C2 C3 . . . . 179.02(12) ?
    N1 C1 C2 C3 . . . . -1.26(12) ?
    O2 C2 C3 C8 . . . . -61.85(16) ?
    O3 C2 C3 C8 . . . . 62.37(16) ?
    C1 C2 C3 C8 . . . . 179.19(12) ?
    O2 C2 C3 C4 . . . . 121.37(11) ?
    O3 C2 C3 C4 . . . . -114.41(11) ?
    C1 C2 C3 C4 . . . . 2.41(12) ?
    C8 C3 C4 C5 . . . . -0.47(18) ?
    C2 C3 C4 C5 . . . . 176.70(11) ?
    C8 C3 C4 N1 . . . . -179.95(10) ?
    C2 C3 C4 N1 . . . . -2.78(13) ?
    C3 C4 C5 C6 . . . . 0.13(18) ?
    N1 C4 C5 C6 . . . . 179.52(11) ?
    C4 C5 C6 C7 . . . . 0.30(18) ?
    C5 C6 C7 C8 . . . . -0.4(2) ?
    C4 C3 C8 C7 . . . . 0.35(18) ?
    C2 C3 C8 C7 . . . . -176.11(12) ?
    C6 C7 C8 C3 . . . . 0.07(19) ?
    O2 C9 C10 C11 . . . . 55.40(14) ?
    C9 C10 C11 O3 . . . . -55.38(13) ?
    O1 C1 N1 C4 . . . . 179.39(12) ?
    C2 C1 N1 C4 . . . . -0.33(13) ?
    C5 C4 N1 C1 . . . . -177.46(12) ?
    C3 C4 N1 C1 . . . . 1.98(14) ?
    O3 C2 O2 C9 . . . . 53.61(13) ?
    C3 C2 O2 C9 . . . . 175.19(9) ?
    C1 C2 O2 C9 . . . . -72.13(12) ?
    C10 C9 O2 C2 . . . . -54.98(13) ?
    O2 C2 O3 C11 . . . . -54.16(13) ?
    C3 C2 O3 C11 . . . . -176.89(9) ?
    C1 C2 O3 C11 . . . . 72.17(12) ?
    C10 C11 O3 C2 . . . . 55.55(13) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 O1 3_756 0.88 1.98 2.8435(14) 165.4 no
data_global
_journal_date_recd_electronic     2009-07-09
_journal_date_accepted     2009-12-15
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o71
_journal_page_last     o78
_journal_paper_category     FO
_journal_coeditor_code     GG3207
_publ_contact_author_name     'Louise Male'
_publ_contact_author_address
;
School of Chemistry
University of Birmingham
Edgbaston
Birmingham B15 2TT
England
;
_publ_contact_author_email     l.male@bham.ac.uk
_publ_contact_author_fax     '0121 414 4403'
_publ_contact_author_phone     '0121 414 7481'
_publ_section_title
;
Seven 3-methylidene-1H-indol-2(3H)-ones related to the
multiple-receptor tyrosine kinase inhibitor sunitinib
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Spencer, John' .
;
School of Science
University of Greenwich at Medway
Central Avenue
Chatham
Kent ME4 4TB
England
;
    'Chowdhry, Babur Z.' .
;
School of Science
University of Greenwich at Medway
Central Avenue
Chatham
Kent ME4 4TB
England
;
    'Hamid, Samiyah' .
;
School of Science
University of Greenwich at Medway
Central Avenue
Chatham
Kent ME4 4TB
England
;
    'Mendham, Andrew P.' .
;
School of Science
University of Greenwich at Medway
Central Avenue
Chatham
Kent ME4 4TB
England
;
    'Male, Louise'
;
Current address: School of Chemistry, University of Birmingham, Edgbaston,
Birmingham B15 2TT, England.
;
;
EPSRC National Crystallography Service
School of Chemistry
University of Southampton
Highfield
Southampton SO17 1BJ
England
;
    'Coles, Simon J.' .
;
EPSRC National Crystallography Service
School of Chemistry
University of Southampton
Highfield
Southampton SO17 1BJ
England
;
    'Hursthouse, Michael B.' .
;
EPSRC National Crystallography Service
School of Chemistry
University of Southampton
Highfield
Southampton SO17 1BJ
England
;
