##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
3a-Phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]\
imidazol-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H14 N2 O'
_chemical_formula_sum     'C16 H14 N2 O'
_chemical_formula_iupac     'C16 H14 N2 O'
_chemical_formula_weight     250.29
_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     7.2966(9)
_cell_length_b     9.1081(11)
_cell_length_c     10.3723(12)
_cell_angle_alpha     66.8030(10)
_cell_angle_beta     88.947(2)
_cell_angle_gamma     82.509(2)
_cell_volume     627.78(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     354
_cell_measurement_theta_min     3
_cell_measurement_theta_max     29
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.23
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.19
_exptl_crystal_density_diffrn     1.324
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     264
_exptl_absorpt_coefficient_mu     0.084
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1998)'
_exptl_absorpt_correction_T_min     0.981
_exptl_absorpt_correction_T_max     0.984
_exptl_special_details     ?
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7155
_diffrn_reflns_av_R_equivalents     0.0162
_diffrn_reflns_av_sigmaI/netI     0.0195
_diffrn_reflns_theta_min     2.14
_diffrn_reflns_theta_max     29.57
_diffrn_reflns_theta_full     29.57
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_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     3492
_reflns_number_gt     3259
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0476
_refine_ls_R_factor_gt     0.0456
_refine_ls_wR_factor_gt     0.1222
_refine_ls_wR_factor_ref     0.1246
_refine_ls_goodness_of_fit_ref     1.005
_refine_ls_restrained_S_all     1.005
_refine_ls_number_reflns     3492
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0792P)²+0.2300P] 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     0.477
_refine_diff_density_min     -0.409
_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     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 1998)'
_computing_data_reduction     'SAINT-Plus (Bruker, 1998)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.61829(11) 0.02564(9) 0.61171(8) 0.01383(17) Uani d . 1 1 . .
    H H1N 0.493(2) 0.0435(19) 0.6207(17) 0.030(4) Uiso d . 1 1 . .
    N N2 0.90402(10) 0.01688(9) 0.70692(8) 0.01328(16) Uani d . 1 1 . .
    O O1 1.21712(9) 0.01286(9) 0.67719(8) 0.01995(17) Uani d . 1 1 . .
    C C1 1.06087(12) 0.08609(11) 0.65663(9) 0.01507(18) Uani d . 1 1 . .
    C C2 0.99897(13) 0.26406(11) 0.57228(10) 0.01707(19) Uani d . 1 1 . .
    H H2A 1.0777 0.3076 0.4907 0.020 Uiso calc R 1 1 . .
    H H2B 1.0020 0.3270 0.6311 0.020 Uiso calc R 1 1 . .
    C C3 0.79979(12) 0.26642(11) 0.52490(10) 0.01545(18) Uani d . 1 1 . .
    H H3A 0.7976 0.2467 0.4377 0.019 Uiso calc R 1 1 . .
    H H3B 0.7237 0.3707 0.5092 0.019 Uiso calc R 1 1 . .
    C C4 0.73073(12) 0.12709(10) 0.64971(9) 0.01247(17) Uani d . 1 1 . .
    C C5 0.69624(12) -0.13486(10) 0.68207(9) 0.01322(18) Uani d . 1 1 . .
    C C6 0.62667(13) -0.27503(11) 0.69730(10) 0.01614(19) Uani d . 1 1 . .
    H H6A 0.5072 -0.2713 0.6603 0.019 Uiso calc R 1 1 . .
    C C7 0.73790(13) -0.42250(11) 0.76887(10) 0.01738(19) Uani d . 1 1 . .
    H H7A 0.6929 -0.5199 0.7800 0.021 Uiso calc R 1 1 . .
    C C8 0.91289(13) -0.42918(11) 0.82398(10) 0.01699(19) Uani d . 1 1 . .
    H H8A 0.9852 -0.5308 0.8720 0.020 Uiso calc R 1 1 . .
    C C9 0.98365(12) -0.28751(11) 0.80946(10) 0.01587(19) Uani d . 1 1 . .
    H H9A 1.1027 -0.2908 0.8468 0.019 Uiso calc R 1 1 . .
    C C10 0.87283(12) -0.14334(10) 0.73858(9) 0.01316(18) Uani d . 1 1 . .
    C C11 0.63184(12) 0.18362(10) 0.75601(9) 0.01345(18) Uani d . 1 1 . .
    C C12 0.46662(13) 0.28868(12) 0.71129(10) 0.01736(19) Uani d . 1 1 . .
    H H12A 0.4231 0.3254 0.6166 0.021 Uiso calc R 1 1 . .
    C C13 0.36550(14) 0.33989(13) 0.80441(11) 0.0213(2) Uani d . 1 1 . .
    H H13A 0.2537 0.4118 0.7730 0.026 Uiso calc R 1 1 . .
    C C14 0.42789(15) 0.28592(13) 0.94374(11) 0.0215(2) Uani d . 1 1 . .
    H H14A 0.3586 0.3206 1.0074 0.026 Uiso calc R 1 1 . .
    C C15 0.59126(15) 0.18152(12) 0.98899(10) 0.0204(2) Uani d . 1 1 . .
    H H15A 0.6339 0.1445 1.0839 0.025 Uiso calc R 1 1 . .
    C C16 0.69403(13) 0.13019(11) 0.89523(10) 0.01684(19) Uani d . 1 1 . .
    H H16A 0.8062 0.0589 0.9267 0.020 Uiso calc R 1 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
    N1 C5 . 1.3968(11) ?
    N1 C4 . 1.4761(11) ?
    N1 H1N . 0.914(16) ?
    N2 C1 . 1.3735(11) ?
    N2 C10 . 1.4126(11) ?
    N2 C4 . 1.4785(11) ?
    O1 C1 . 1.2201(11) ?
    C1 C2 . 1.5177(13) ?
    C2 C3 . 1.5375(13) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.5456(12) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C11 . 1.5240(12) ?
    C5 C6 . 1.3855(12) ?
    C5 C10 . 1.4057(12) ?
    C6 C7 . 1.4022(13) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.3928(13) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.4043(13) ?
    C8 H8A . 0.9500 ?
    C9 C10 . 1.3795(12) ?
    C9 H9A . 0.9500 ?
    C11 C16 . 1.3932(13) ?
    C11 C12 . 1.3979(12) ?
    C12 C13 . 1.3907(13) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.3941(15) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.3853(15) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.4023(13) ?
    C15 H15A . 0.9500 ?
    C16 H16A . 0.9500 ?
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
    C5 N1 C4 . . 107.81(7) ?
    C5 N1 H1N . . 114.1(10) ?
    C4 N1 H1N . . 116.3(10) ?
    C1 N2 C10 . . 128.12(8) ?
    C1 N2 C4 . . 113.60(7) ?
    C10 N2 C4 . . 109.45(7) ?
    O1 C1 N2 . . 124.57(9) ?
    O1 C1 C2 . . 128.65(8) ?
    N2 C1 C2 . . 106.78(7) ?
    C1 C2 C3 . . 102.85(7) ?
    C1 C2 H2A . . 111.2 ?
    C3 C2 H2A . . 111.2 ?
    C1 C2 H2B . . 111.2 ?
    C3 C2 H2B . . 111.2 ?
    H2A C2 H2B . . 109.1 ?
    C2 C3 C4 . . 103.00(7) ?
    C2 C3 H3A . . 111.2 ?
    C4 C3 H3A . . 111.2 ?
    C2 C3 H3B . . 111.2 ?
    C4 C3 H3B . . 111.2 ?
    H3A C3 H3B . . 109.1 ?
    N1 C4 N2 . . 102.36(7) ?
    N1 C4 C11 . . 110.26(7) ?
    N2 C4 C11 . . 113.36(7) ?
    N1 C4 C3 . . 115.50(7) ?
    N2 C4 C3 . . 102.07(7) ?
    C11 C4 C3 . . 112.65(7) ?
    C6 C5 N1 . . 129.53(8) ?
    C6 C5 C10 . . 119.99(8) ?
    N1 C5 C10 . . 110.45(8) ?
    C5 C6 C7 . . 118.01(8) ?
    C5 C6 H6A . . 121.0 ?
    C7 C6 H6A . . 121.0 ?
    C8 C7 C6 . . 121.42(9) ?
    C8 C7 H7A . . 119.3 ?
    C6 C7 H7A . . 119.3 ?
    C7 C8 C9 . . 120.80(8) ?
    C7 C8 H8A . . 119.6 ?
    C9 C8 H8A . . 119.6 ?
    C10 C9 C8 . . 117.14(8) ?
    C10 C9 H9A . . 121.4 ?
    C8 C9 H9A . . 121.4 ?
    C9 C10 C5 . . 122.64(8) ?
    C9 C10 N2 . . 130.60(8) ?
    C5 C10 N2 . . 106.76(7) ?
    C16 C11 C12 . . 119.26(8) ?
    C16 C11 C4 . . 123.18(8) ?
    C12 C11 C4 . . 117.49(8) ?
    C13 C12 C11 . . 120.48(9) ?
    C13 C12 H12A . . 119.8 ?
    C11 C12 H12A . . 119.8 ?
    C12 C13 C14 . . 120.11(9) ?
    C12 C13 H13A . . 119.9 ?
    C14 C13 H13A . . 119.9 ?
    C15 C14 C13 . . 119.78(9) ?
    C15 C14 H14A . . 120.1 ?
    C13 C14 H14A . . 120.1 ?
    C14 C15 C16 . . 120.27(9) ?
    C14 C15 H15A . . 119.9 ?
    C16 C15 H15A . . 119.9 ?
    C11 C16 C15 . . 120.09(9) ?
    C11 C16 H16A . . 120.0 ?
    C15 C16 H16A . . 120.0 ?
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
    C10 N2 C1 O1 . . . . -27.81(15) ?
    C4 N2 C1 O1 . . . . -171.39(9) ?
    C10 N2 C1 C2 . . . . 151.31(9) ?
    C4 N2 C1 C2 . . . . 7.74(10) ?
    O1 C1 C2 C3 . . . . 152.84(9) ?
    N2 C1 C2 C3 . . . . -26.24(9) ?
    C1 C2 C3 C4 . . . . 33.88(9) ?
    C5 N1 C4 N2 . . . . 17.45(9) ?
    C5 N1 C4 C11 . . . . -103.45(8) ?
    C5 N1 C4 C3 . . . . 127.43(8) ?
    C1 N2 C4 N1 . . . . 133.80(8) ?
    C10 N2 C4 N1 . . . . -16.51(9) ?
    C1 N2 C4 C11 . . . . -107.46(8) ?
    C10 N2 C4 C11 . . . . 102.23(8) ?
    C1 N2 C4 C3 . . . . 13.96(9) ?
    C10 N2 C4 C3 . . . . -136.34(7) ?
    C2 C3 C4 N1 . . . . -139.28(8) ?
    C2 C3 C4 N2 . . . . -29.13(8) ?
    C2 C3 C4 C11 . . . . 92.78(8) ?
    C4 N1 C5 C6 . . . . 169.27(9) ?
    C4 N1 C5 C10 . . . . -12.80(10) ?
    N1 C5 C6 C7 . . . . 177.26(9) ?
    C10 C5 C6 C7 . . . . -0.50(13) ?
    C5 C6 C7 C8 . . . . 0.30(14) ?
    C6 C7 C8 C9 . . . . 0.02(14) ?
    C7 C8 C9 C10 . . . . -0.13(14) ?
    C8 C9 C10 C5 . . . . -0.07(14) ?
    C8 C9 C10 N2 . . . . -179.87(9) ?
    C6 C5 C10 C9 . . . . 0.40(14) ?
    N1 C5 C10 C9 . . . . -177.76(8) ?
    C6 C5 C10 N2 . . . . -179.76(8) ?
    N1 C5 C10 N2 . . . . 2.08(10) ?
    C1 N2 C10 C9 . . . . 44.60(15) ?
    C4 N2 C10 C9 . . . . -170.65(9) ?
    C1 N2 C10 C5 . . . . -135.22(9) ?
    C4 N2 C10 C5 . . . . 9.53(9) ?
    N1 C4 C11 C16 . . . . 111.04(9) ?
    N2 C4 C11 C16 . . . . -3.03(12) ?
    C3 C4 C11 C16 . . . . -118.31(9) ?
    N1 C4 C11 C12 . . . . -66.08(10) ?
    N2 C4 C11 C12 . . . . 179.85(8) ?
    C3 C4 C11 C12 . . . . 64.57(10) ?
    C16 C11 C12 C13 . . . . 0.20(14) ?
    C4 C11 C12 C13 . . . . 177.44(8) ?
    C11 C12 C13 C14 . . . . -0.35(15) ?
    C12 C13 C14 C15 . . . . 0.21(16) ?
    C13 C14 C15 C16 . . . . 0.08(15) ?
    C12 C11 C16 C15 . . . . 0.09(14) ?
    C4 C11 C16 C15 . . . . -176.98(8) ?
    C14 C15 C16 C11 . . . . -0.23(15) ?
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
    N1 H1N O1 1_455 0.914(16) 2.112(17) 2.9994(11) 163.4(14)
data_global
_journal_date_recd_electronic     2013-05-22
_journal_date_accepted     2013-06-10
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2013
_journal_volume     69
_journal_issue      8
_journal_page_first     880
_journal_page_last     883
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270113016119
_journal_coeditor_code     EG3127
_publ_contact_author_name     'Vyacheslav Grinev'
_publ_contact_author_address
;
Institute of Biochemistry and Physiology of Plants and Microorganisms
Russian Academy of Sciences
Entuziastov Avenue 13
410049 Saratov
Russian Federation
;
_publ_contact_author_email     grinev@ibppm.sgu.ru
_publ_contact_author_fax     '7(8452)970383'
_publ_contact_author_phone     '7(8452)970383'
_publ_section_title
;\
3a-Phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]\
imidazol-1-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Grinev, Vyacheslav S.'
;
Institute of Biochemistry and Physiology of Plants and Microorganisms
Russian Academy of Sciences
Entuziastov Avenue 13
410049 Saratov
Russian Federation
;
    'Egorova, Alevtina Yu.'
;
Chernyshevsky Saratov State University
83 Ul. Astrakhanskay
410001 Saratov
Russian Federation
;
