##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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 2.1.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL97 CIF, edited IUCr template'
_journal_date_recd_electronic     2005-09-08
_journal_date_accepted     2005-09-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     10
_journal_page_first     o3254
_journal_page_last     o3256
_journal_paper_category     EO
_journal_coeditor_code     AC6200
_publ_contact_author_name     'Dr P. A. Crooks'
_publ_contact_author_address
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington KY 40536
USA
;
_publ_contact_author_email     'pcrooks@uky.edu'
_publ_contact_author_fax     '859 257 2585'
_publ_contact_author_phone     '859 257 1718'
_publ_section_title
;
(Z)-2-(3-Nitrobenzylidene)-1-azabicyclo[2.2.2]octan-3-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Sonar, Vijayakumar N.'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington KY 40536
USA
;
    'Parkin, Sean'
;
Department of Chemistry
University of Kentucky
Lexington KY 40506
USA
;
    'Crooks, Peter A.'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington KY 40536
USA
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
(Z)-2-(3-Nitrobenzylidene)-1-azabicyclo[2.2.2]octan-3-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H14 N2 O3'
_chemical_formula_sum     'C14 H14 N2 O3'
_chemical_formula_iupac     'C14 H14 N2 O3'
_chemical_formula_weight     258.27
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/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     5.80950(10)
_cell_length_b     24.2920(4)
_cell_length_c     8.5473(2)
_cell_angle_alpha     90.00
_cell_angle_beta     99.2211(8)
_cell_angle_gamma     90.00
_cell_volume     1190.64(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4654
_cell_measurement_theta_min     1
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     90.0(2)
_exptl_crystal_description     'needle'
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.441
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     544
_exptl_absorpt_coefficient_mu     0.103
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.9698
_exptl_absorpt_correction_T_max     0.9797
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     90.0(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     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean     18
_diffrn_reflns_number     9090
_diffrn_reflns_av_R_equivalents     0.0270
_diffrn_reflns_av_sigmaI/netI     0.0292
_diffrn_reflns_theta_min     1.68
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_theta_full     27.49
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -29
_diffrn_reflns_limit_k_max     31
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     <1
_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 > 2sigma(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     2739
_reflns_number_gt     2275
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0483
_refine_ls_R_factor_gt     0.0373
_refine_ls_wR_factor_gt     0.0919
_refine_ls_wR_factor_ref     0.0985
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     2739
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w = 1/[σ²(Fo²)+(0.0463P)²+0.444P] 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     0.320
_refine_diff_density_min     -0.225
_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'
    'O' 'O' 0.0106 0.0060
                         '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'
_computing_data_collection     'COLLECT (Nonius, 1999)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'XP in SHELXTL/PC (Sheldrick, 1995)'
_computing_publication_material     'SHELXL97 and local procedures'
loop_
    _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
    _atom_site_type_symbol
    N1 0.13636(17) 0.37496(4) 0.69584(11) 0.0142(2) Uani d . 1 . . N
    O1 0.26010(15) 0.51717(4) 0.61669(11) 0.0207(2) Uani d . 1 . . O
    C1 0.3331(2) 0.36044(5) 0.38323(13) 0.0143(2) Uani d . 1 . . C
    N2 0.71988(19) 0.30897(5) 0.10506(12) 0.0241(3) Uani d . 1 . . N
    O2 0.82297(17) 0.35203(4) 0.08570(11) 0.0295(2) Uani d . 1 . . O
    C2 0.1891(2) 0.31439(5) 0.38853(14) 0.0170(3) Uani d . 1 . . C
    H2 0.0669 0.3157 0.4502 0.020 Uiso calc R 1 . . H
    O3 0.75894(18) 0.26495(5) 0.04314(12) 0.0372(3) Uani d . 1 . . O
    C3 0.2232(2) 0.26694(5) 0.30474(15) 0.0203(3) Uani d . 1 . . C
    H3 0.1233 0.2362 0.3090 0.024 Uiso calc R 1 . . H
    C4 0.4017(2) 0.26396(5) 0.21472(15) 0.0214(3) Uani d . 1 . . C
    H4 0.4293 0.2312 0.1600 0.026 Uiso calc R 1 . . H
    C5 0.5382(2) 0.31023(5) 0.20723(13) 0.0186(3) Uani d . 1 . . C
    C6 0.5076(2) 0.35851(5) 0.28781(13) 0.0159(2) Uani d . 1 . . C
    H6 0.6032 0.3897 0.2785 0.019 Uiso calc R 1 . . H
    C7 0.3061(2) 0.41158(5) 0.46954(14) 0.0146(2) Uani d . 1 . . C
    H7 0.3582 0.4441 0.4244 0.018 Uiso calc R 1 . . H
    C8 0.21777(19) 0.41853(5) 0.60342(14) 0.0141(2) Uani d . 1 . . C
    C9 0.1975(2) 0.47444(5) 0.67265(14) 0.0151(2) Uani d . 1 . . C
    C10 0.0897(2) 0.47105(5) 0.82161(14) 0.0161(3) Uani d . 1 . . C
    H10 0.0730 0.5084 0.8675 0.019 Uiso calc R 1 . . H
    C11 -0.1492(2) 0.44243(5) 0.77922(15) 0.0175(3) Uani d . 1 . . C
    H11A -0.2546 0.4653 0.7029 0.021 Uiso calc R 1 . . H
    H11B -0.2212 0.4377 0.8758 0.021 Uiso calc R 1 . . H
    C12 -0.1130(2) 0.38538(5) 0.70491(14) 0.0170(3) Uani d . 1 . . C
    H12A -0.1711 0.3562 0.7695 0.020 Uiso calc R 1 . . H
    H12B -0.2050 0.3837 0.5970 0.020 Uiso calc R 1 . . H
    C13 0.2496(2) 0.43407(5) 0.93859(14) 0.0177(3) Uani d . 1 . . C
    H13A 0.1830 0.4294 1.0374 0.021 Uiso calc R 1 . . H
    H13B 0.4056 0.4511 0.9658 0.021 Uiso calc R 1 . . H
    C14 0.2704(2) 0.37742(5) 0.85903(14) 0.0166(3) Uani d . 1 . . C
    H14A 0.4367 0.3698 0.8550 0.020 Uiso calc R 1 . . H
    H14B 0.2128 0.3484 0.9244 0.020 Uiso calc R 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N1 0.0145(5) 0.0147(5) 0.0139(5) -0.0013(4) 0.0035(4) 0.0013(4)
    O1 0.0226(5) 0.0149(4) 0.0266(5) -0.0030(4) 0.0097(4) -0.0008(4)
    C1 0.0159(6) 0.0150(6) 0.0114(5) 0.0019(4) -0.0001(4) 0.0014(4)
    N2 0.0217(6) 0.0365(7) 0.0133(5) 0.0108(5) -0.0001(4) -0.0041(5)
    O2 0.0279(5) 0.0408(6) 0.0220(5) 0.0072(5) 0.0107(4) 0.0060(4)
    C2 0.0185(6) 0.0172(6) 0.0144(6) 0.0001(5) -0.0006(4) 0.0021(5)
    O3 0.0290(5) 0.0495(7) 0.0321(6) 0.0121(5) 0.0022(4) -0.0235(5)
    C3 0.0254(6) 0.0148(6) 0.0180(6) -0.0015(5) -0.0043(5) 0.0007(5)
    C4 0.0278(7) 0.0177(6) 0.0160(6) 0.0058(5) -0.0047(5) -0.0038(5)
    C5 0.0197(6) 0.0243(7) 0.0110(5) 0.0067(5) 0.0002(5) -0.0013(5)
    C6 0.0169(6) 0.0174(6) 0.0130(5) 0.0015(5) 0.0007(4) 0.0015(5)
    C7 0.0137(5) 0.0137(6) 0.0165(6) -0.0003(4) 0.0026(4) 0.0013(4)
    C8 0.0124(5) 0.0130(6) 0.0168(6) -0.0004(4) 0.0023(4) 0.0006(4)
    C9 0.0111(5) 0.0161(6) 0.0182(6) -0.0006(4) 0.0029(4) -0.0009(5)
    C10 0.0167(6) 0.0138(6) 0.0188(6) 0.0011(4) 0.0057(5) -0.0021(5)
    C11 0.0144(6) 0.0197(6) 0.0195(6) 0.0018(5) 0.0058(5) 0.0018(5)
    C12 0.0139(6) 0.0201(6) 0.0174(6) -0.0029(5) 0.0036(4) -0.0005(5)
    C13 0.0174(6) 0.0191(6) 0.0166(6) 0.0007(5) 0.0024(5) -0.0029(5)
    C14 0.0168(6) 0.0172(6) 0.0156(6) 0.0020(5) 0.0018(4) 0.0009(5)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 C8 . 1.4448(15) y
    N1 C12 . 1.4846(15) y
    N1 C14 . 1.4858(15) ?
    O1 C9 . 1.2223(14) y
    C1 C6 . 1.4003(16) ?
    C1 C2 . 1.4020(17) ?
    C1 C7 . 1.4660(16) y
    N2 O2 . 1.2297(16) ?
    N2 O3 . 1.2303(15) y
    N2 C5 . 1.4739(16) y
    C2 C3 . 1.3878(17) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.3891(19) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.3831(19) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.3857(17) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.3376(17) y
    C7 H7 . 0.9500 ?
    C8 C9 . 1.4937(16) y
    C9 C10 . 1.5085(16) ?
    C10 C13 . 1.5401(17) ?
    C10 C11 . 1.5426(16) ?
    C10 H10 . 1.0000 ?
    C11 C12 . 1.5529(17) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.5483(17) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
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
    C8 N1 C12 . . 108.14(9) ?
    C8 N1 C14 . . 108.39(9) ?
    C12 N1 C14 . . 108.24(9) ?
    C6 C1 C2 . . 118.92(11) ?
    C6 C1 C7 . . 117.87(11) ?
    C2 C1 C7 . . 123.18(11) y
    O2 N2 O3 . . 123.65(11) y
    O2 N2 C5 . . 118.19(11) y
    O3 N2 C5 . . 118.16(12) ?
    C3 C2 C1 . . 120.72(12) ?
    C3 C2 H2 . . 119.6 ?
    C1 C2 H2 . . 119.6 ?
    C2 C3 C4 . . 120.67(12) ?
    C2 C3 H3 . . 119.7 ?
    C4 C3 H3 . . 119.7 ?
    C5 C4 C3 . . 117.90(11) ?
    C5 C4 H4 . . 121.1 ?
    C3 C4 H4 . . 121.1 ?
    C4 C5 C6 . . 123.00(11) ?
    C4 C5 N2 . . 118.73(11) ?
    C6 C5 N2 . . 118.24(11) y
    C5 C6 C1 . . 118.72(11) ?
    C5 C6 H6 . . 120.6 ?
    C1 C6 H6 . . 120.6 ?
    C8 C7 C1 . . 128.62(11) y
    C8 C7 H7 . . 115.7 ?
    C1 C7 H7 . . 115.7 ?
    C7 C8 N1 . . 125.40(11) y
    C7 C8 C9 . . 121.26(11) ?
    N1 C8 C9 . . 113.33(10) y
    O1 C9 C8 . . 124.75(11) ?
    O1 C9 C10 . . 124.49(11) ?
    C8 C9 C10 . . 110.76(10) y
    C9 C10 C13 . . 106.92(9) ?
    C9 C10 C11 . . 107.81(10) ?
    C13 C10 C11 . . 108.41(10) ?
    C9 C10 H10 . . 111.2 ?
    C13 C10 H10 . . 111.2 ?
    C11 C10 H10 . . 111.2 ?
    C10 C11 C12 . . 108.82(9) ?
    C10 C11 H11A . . 109.9 ?
    C12 C11 H11A . . 109.9 ?
    C10 C11 H11B . . 109.9 ?
    C12 C11 H11B . . 109.9 ?
    H11A C11 H11B . . 108.3 ?
    N1 C12 C11 . . 111.76(9) ?
    N1 C12 H12A . . 109.3 ?
    C11 C12 H12A . . 109.3 ?
    N1 C12 H12B . . 109.3 ?
    C11 C12 H12B . . 109.3 ?
    H12A C12 H12B . . 107.9 ?
    C10 C13 C14 . . 108.35(10) ?
    C10 C13 H13A . . 110.0 ?
    C14 C13 H13A . . 110.0 ?
    C10 C13 H13B . . 110.0 ?
    C14 C13 H13B . . 110.0 ?
    H13A C13 H13B . . 108.4 ?
    N1 C14 C13 . . 112.46(9) ?
    N1 C14 H14A . . 109.1 ?
    C13 C14 H14A . . 109.1 ?
    N1 C14 H14B . . 109.1 ?
    C13 C14 H14B . . 109.1 ?
    H14A C14 H14B . . 107.8 ?
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
    C6 C1 C2 C3 . . . . 2.03(17) ?
    C7 C1 C2 C3 . . . . -179.79(11) ?
    C1 C2 C3 C4 . . . . 0.46(18) ?
    C2 C3 C4 C5 . . . . -2.17(18) ?
    C3 C4 C5 C6 . . . . 1.45(18) ?
    C3 C4 C5 N2 . . . . -176.53(10) ?
    O2 N2 C5 C4 . . . . 172.24(11) ?
    O3 N2 C5 C4 . . . . -7.34(16) ?
    O2 N2 C5 C6 . . . . -5.84(16) ?
    O3 N2 C5 C6 . . . . 174.58(11) ?
    C4 C5 C6 C1 . . . . 1.00(18) ?
    N2 C5 C6 C1 . . . . 179.00(10) ?
    C2 C1 C6 C5 . . . . -2.72(16) ?
    C7 C1 C6 C5 . . . . 179.01(10) ?
    C6 C1 C7 C8 . . . . -154.52(12) y
    C2 C1 C7 C8 . . . . 27.29(19) y
    C1 C7 C8 N1 . . . . 2.5(2) y
    C1 C7 C8 C9 . . . . -178.24(11) ?
    C12 N1 C8 C7 . . . . -120.83(12) ?
    C14 N1 C8 C7 . . . . 122.04(12) ?
    C12 N1 C8 C9 . . . . 59.84(12) ?
    C14 N1 C8 C9 . . . . -57.30(12) ?
    C7 C8 C9 O1 . . . . -0.98(19) y
    N1 C8 C9 O1 . . . . 178.38(11) ?
    C7 C8 C9 C10 . . . . 179.17(11) ?
    N1 C8 C9 C10 . . . . -1.46(14) ?
    O1 C9 C10 C13 . . . . -120.35(13) ?
    C8 C9 C10 C13 . . . . 59.50(12) ?
    O1 C9 C10 C11 . . . . 123.26(12) ?
    C8 C9 C10 C11 . . . . -56.89(12) ?
    C9 C10 C11 C12 . . . . 56.53(12) ?
    C13 C10 C11 C12 . . . . -58.88(12) ?
    C8 N1 C12 C11 . . . . -57.98(12) ?
    C14 N1 C12 C11 . . . . 59.25(12) ?
    C10 C11 C12 N1 . . . . -0.11(13) ?
    C9 C10 C13 C14 . . . . -57.64(12) ?
    C11 C10 C13 C14 . . . . 58.36(12) ?
    C8 N1 C14 C13 . . . . 57.12(12) ?
    C12 N1 C14 C13 . . . . -59.95(12) ?
    C10 C13 C14 N1 . . . . 0.71(13) ?
