#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/58/2015816.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2015816
loop_
_publ_author_name
'Sonar, Vijayakumar N.'
'Parkin, Sean'
'Crooks, Peter A.'
_publ_section_title
(Z)-2-(1-Benzyl-5-nitro-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one
_journal_coeditor_code           SK3086
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o135
_journal_page_last               o136
_journal_paper_doi               10.1107/S0108270106055971
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C23 H21 N3 O3'
_chemical_formula_moiety         'C23 H21 N3 O3'
_chemical_formula_sum            'C23 H21 N3 O3'
_chemical_formula_weight         387.43
_chemical_name_systematic
(Z)-2-(1-Benzyl-5-nitro-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.1103(5)
_cell_angle_beta                 104.3081(5)
_cell_angle_gamma                106.1250(6)
_cell_formula_units_Z            2
_cell_length_a                   9.35600(10)
_cell_length_b                   9.40490(10)
_cell_length_c                   11.1174(2)
_cell_measurement_reflns_used    4140
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     907.99(2)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1995)'
_computing_publication_material  'SHELX97 and local procedures'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8270
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0517P)²+0.3204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                3404
_reflns_number_total             4162
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3086.cif
_cod_data_source_block           I
_cod_database_code               2015816
_cod_database_fobs_code          2015816
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N N1 0.52413(12) 0.42763(12) 0.35572(10) 0.0157(2) Uani d . 1
N N2 0.02312(12) 0.20441(12) 0.24670(10) 0.0171(2) Uani d . 1
N N3 0.75088(12) 0.14362(12) 0.76382(10) 0.0185(2) Uani d . 1
O O1 -0.04971(10) -0.14407(10) 0.39073(8) 0.0182(2) Uani d . 1
O O2 0.65436(11) 0.04323(11) 0.79617(9) 0.0259(2) Uani d . 1
O O3 0.88828(10) 0.18360(11) 0.82027(8) 0.0227(2) Uani d . 1
C C2 0.37220(14) 0.34516(14) 0.32450(11) 0.0165(3) Uani d . 1
H H2 0.2943 0.3640 0.2590 0.020 Uiso calc R 1
C C3 0.34877(14) 0.23124(14) 0.40159(11) 0.0155(3) Uani d . 1
C C4 0.49666(14) 0.24628(14) 0.48707(11) 0.0151(3) Uani d . 1
C C5 0.54642(14) 0.16980(14) 0.58896(11) 0.0160(3) Uani d . 1
H H5 0.4777 0.0864 0.6127 0.019 Uiso calc R 1
C C6 0.69931(14) 0.22001(14) 0.65400(11) 0.0167(3) Uani d . 1
C C7 0.80643(15) 0.34117(15) 0.62215(12) 0.0186(3) Uani d . 1
H H7 0.9108 0.3704 0.6696 0.022 Uiso calc R 1
C C8 0.75854(14) 0.41759(14) 0.52104(12) 0.0176(3) Uani d . 1
H H8 0.8286 0.4998 0.4972 0.021 Uiso calc R 1
C C9 0.60372(14) 0.36970(14) 0.45524(11) 0.0152(3) Uani d . 1
C C10 0.21065(14) 0.11328(14) 0.39824(11) 0.0153(3) Uani d . 1
H H10 0.2232 0.0372 0.4525 0.018 Uiso calc R 1
C C11 0.06732(14) 0.09675(13) 0.32898(11) 0.0148(3) Uani d . 1
C C12 -0.05007(15) 0.12965(15) 0.12032(12) 0.0213(3) Uani d . 1
H H12A 0.0259 0.0935 0.0905 0.026 Uiso calc R 1
H H12B -0.0811 0.2024 0.0629 0.026 Uiso calc R 1
C C13 -0.19333(15) -0.00278(15) 0.11735(12) 0.0214(3) Uani d . 1
H H13A -0.2864 0.0155 0.0626 0.026 Uiso calc R 1
H H13B -0.1802 -0.0949 0.0843 0.026 Uiso calc R 1
C C14 -0.21145(14) -0.01971(14) 0.25141(11) 0.0167(3) Uani d . 1
H H14 -0.3001 -0.1071 0.2545 0.020 Uiso calc R 1
C C15 -0.23320(14) 0.12513(14) 0.29833(12) 0.0188(3) Uani d . 1
H H15A -0.2409 0.1190 0.3855 0.023 Uiso calc R 1
H H15B -0.3293 0.1408 0.2466 0.023 Uiso calc R 1
C C16 -0.09318(15) 0.25586(14) 0.29029(13) 0.0197(3) Uani d . 1
H H16A -0.1291 0.3259 0.2323 0.024 Uiso calc R 1
H H16B -0.0446 0.3098 0.3734 0.024 Uiso calc R 1
C C17 -0.06227(14) -0.03588(14) 0.33223(11) 0.0151(3) Uani d . 1
C C18 0.59205(14) 0.54717(14) 0.28537(11) 0.0166(3) Uani d . 1
H H18A 0.6825 0.6175 0.3426 0.020 Uiso calc R 1
H H18B 0.5160 0.6018 0.2523 0.020 Uiso calc R 1
C C19 0.64224(14) 0.49417(14) 0.17790(11) 0.0150(3) Uani d . 1
C C20 0.55885(14) 0.36204(14) 0.10540(12) 0.0177(3) Uani d . 1
H H20 0.4704 0.2995 0.1255 0.021 Uiso calc R 1
C C21 0.60486(15) 0.32176(15) 0.00391(12) 0.0202(3) Uani d . 1
H H21 0.5483 0.2313 -0.0447 0.024 Uiso calc R 1
C C22 0.73326(15) 0.41330(15) -0.02681(12) 0.0208(3) Uani d . 1
H H22 0.7638 0.3862 -0.0968 0.025 Uiso calc R 1
C C23 0.81668(15) 0.54441(15) 0.04513(12) 0.0203(3) Uani d . 1
H H23 0.9045 0.6072 0.0244 0.024 Uiso calc R 1
C C24 0.77199(14) 0.58402(14) 0.14748(12) 0.0170(3) Uani d . 1
H H24 0.8305 0.6732 0.1972 0.020 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C9 109.17(10) ?
C2 N1 C18 124.78(10) ?
C9 N1 C18 125.74(10) ?
C11 N2 C12 108.33(10) ?
C11 N2 C16 107.98(10) ?
C12 N2 C16 108.31(10) ?
O3 N3 O2 123.14(11) ?
O3 N3 C6 118.44(11) ?
O2 N3 C6 118.41(10) ?
N1 C2 C3 110.36(11) ?
N1 C2 H2 124.8 ?
C3 C2 H2 124.8 ?
C2 C3 C4 105.78(11) ?
C2 C3 C10 129.41(11) y
C4 C3 C10 124.73(11) ?
C5 C4 C9 119.13(11) ?
C5 C4 C3 133.39(12) ?
C9 C4 C3 107.44(11) ?
C6 C5 C4 117.42(12) ?
C6 C5 H5 121.3 ?
C4 C5 H5 121.3 ?
C5 C6 C7 123.75(12) ?
C5 C6 N3 117.66(11) ?
C7 C6 N3 118.58(11) ?
C8 C7 C6 119.35(12) ?
C8 C7 H7 120.3 ?
C6 C7 H7 120.3 ?
C7 C8 C9 117.69(12) ?
C7 C8 H8 121.2 ?
C9 C8 H8 121.2 ?
N1 C9 C8 130.09(12) ?
N1 C9 C4 107.24(11) ?
C8 C9 C4 122.65(11) ?
C11 C10 C3 128.65(12) y
C11 C10 H10 115.7 ?
C3 C10 H10 115.7 ?
C10 C11 N2 124.03(11) ?
C10 C11 C17 122.04(11) y
N2 C11 C17 113.92(10) y
N2 C12 C13 112.22(10) ?
N2 C12 H12A 109.2 ?
C13 C12 H12A 109.2 ?
N2 C12 H12B 109.2 ?
C13 C12 H12B 109.2 ?
H12A C12 H12B 107.9 ?
C14 C13 C12 108.38(10) ?
C14 C13 H13A 110.0 ?
C12 C13 H13A 110.0 ?
C14 C13 H13B 110.0 ?
C12 C13 H13B 110.0 ?
H13A C13 H13B 108.4 ?
C17 C14 C15 107.42(10) ?
C17 C14 C13 107.62(10) ?
C15 C14 C13 108.20(10) ?
C17 C14 H14 111.1 ?
C15 C14 H14 111.1 ?
C13 C14 H14 111.1 ?
C14 C15 C16 108.60(10) ?
C14 C15 H15A 110.0 ?
C16 C15 H15A 110.0 ?
C14 C15 H15B 110.0 ?
C16 C15 H15B 110.0 ?
H15A C15 H15B 108.4 ?
N2 C16 C15 111.96(10) ?
N2 C16 H16A 109.2 ?
C15 C16 H16A 109.2 ?
N2 C16 H16B 109.2 ?
C15 C16 H16B 109.2 ?
H16A C16 H16B 107.9 ?
O1 C17 C11 124.95(11) ?
O1 C17 C14 124.73(11) ?
C11 C17 C14 110.32(10) ?
N1 C18 C19 113.81(10) ?
N1 C18 H18A 108.8 ?
C19 C18 H18A 108.8 ?
N1 C18 H18B 108.8 ?
C19 C18 H18B 108.8 ?
H18A C18 H18B 107.7 ?
C24 C19 C20 119.12(11) ?
C24 C19 C18 118.58(11) y
C20 C19 C18 122.23(11) y
C21 C20 C19 120.20(12) ?
C21 C20 H20 119.9 ?
C19 C20 H20 119.9 ?
C22 C21 C20 120.25(12) ?
C22 C21 H21 119.9 ?
C20 C21 H21 119.9 ?
C23 C22 C21 119.75(12) ?
C23 C22 H22 120.1 ?
C21 C22 H22 120.1 ?
C22 C23 C24 120.09(12) ?
C22 C23 H23 120.0 ?
C24 C23 H23 120.0 ?
C23 C24 C19 120.57(12) ?
C23 C24 H24 119.7 ?
C19 C24 H24 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.3731(16) ?
N1 C9 1.3769(16) ?
N1 C18 1.4601(16) ?
N2 C11 1.4429(15) y
N2 C12 1.4800(16) ?
N2 C16 1.4850(16) ?
N3 O3 1.2328(14) ?
N3 O2 1.2347(14) ?
N3 C6 1.4643(16) y
O1 C17 1.2261(15) ?
C2 C3 1.3771(18) ?
C2 H2 0.9500 ?
C3 C4 1.4417(17) ?
C3 C10 1.4428(17) ?
C4 C5 1.3949(17) ?
C4 C9 1.4167(17) ?
C5 C6 1.3799(17) ?
C5 H5 0.9500 ?
C6 C7 1.4039(18) ?
C7 C8 1.3834(18) ?
C7 H7 0.9500 ?
C8 C9 1.3960(17) ?
C8 H8 0.9500 ?
C10 C11 1.3374(17) y
C10 H10 0.9500 ?
C11 C17 1.4863(17) y
C12 C13 1.5490(18) ?
C12 H12A 0.9900 ?
C12 H12B 0.9900 ?
C13 C14 1.5447(17) ?
C13 H13A 0.9900 ?
C13 H13B 0.9900 ?
C14 C17 1.5090(17) ?
C14 C15 1.5404(18) ?
C14 H14 1.0000 ?
C15 C16 1.5490(17) ?
C15 H15A 0.9900 ?
C15 H15B 0.9900 ?
C16 H16A 0.9900 ?
C16 H16B 0.9900 ?
C18 C19 1.5170(17) ?
C18 H18A 0.9900 ?
C18 H18B 0.9900 ?
C19 C24 1.3915(17) ?
C19 C20 1.3962(18) ?
C20 C21 1.3895(18) ?
C20 H20 0.9500 ?
C21 C22 1.3894(19) ?
C21 H21 0.9500 ?
C22 C23 1.3865(19) ?
C22 H22 0.9500 ?
C23 C24 1.3887(18) ?
C23 H23 0.9500 ?
C24 H24 0.9500 ?
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
_geom_torsion_publ_flag
C9 N1 C2 C3 -0.46(14) ?
C18 N1 C2 C3 173.43(11) ?
N1 C2 C3 C4 0.75(14) ?
N1 C2 C3 C10 -176.05(12) ?
C2 C3 C4 C5 176.95(13) ?
C10 C3 C4 C5 -6.0(2) ?
C2 C3 C4 C9 -0.76(13) ?
C10 C3 C4 C9 176.23(11) ?
C9 C4 C5 C6 0.22(17) ?
C3 C4 C5 C6 -177.29(12) ?
C4 C5 C6 C7 -0.98(19) ?
C4 C5 C6 N3 177.76(11) ?
O3 N3 C6 C5 177.38(11) ?
O2 N3 C6 C5 -3.33(17) y
O3 N3 C6 C7 -3.81(17) y
O2 N3 C6 C7 175.47(11) ?
C5 C6 C7 C8 0.78(19) ?
N3 C6 C7 C8 -177.95(11) ?
C6 C7 C8 C9 0.20(18) ?
C2 N1 C9 C8 -178.21(12) ?
C18 N1 C9 C8 8.0(2) ?
C2 N1 C9 C4 -0.04(13) ?
C18 N1 C9 C4 -173.86(11) ?
C7 C8 C9 N1 176.99(12) ?
C7 C8 C9 C4 -0.94(18) ?
C5 C4 C9 N1 -177.60(11) ?
C3 C4 C9 N1 0.50(13) ?
C5 C4 C9 C8 0.74(18) ?
C3 C4 C9 C8 178.84(11) ?
C2 C3 C10 C11 -9.2(2) ?
C4 C3 C10 C11 174.55(12) ?
C3 C10 C11 N2 -3.9(2) ?
C3 C10 C11 C17 177.09(11) ?
C12 N2 C11 C10 124.07(13) ?
C16 N2 C11 C10 -118.84(13) ?
C12 N2 C11 C17 -56.82(13) ?
C16 N2 C11 C17 60.27(13) ?
C11 N2 C12 C13 58.82(13) ?
C16 N2 C12 C13 -58.06(13) ?
N2 C12 C13 C14 -2.34(15) ?
C12 C13 C14 C17 -55.53(14) ?
C12 C13 C14 C15 60.26(13) ?
C17 C14 C15 C16 58.61(13) ?
C13 C14 C15 C16 -57.31(13) ?
C11 N2 C16 C15 -55.91(13) ?
C12 N2 C16 C15 61.19(13) ?
C14 C15 C16 N2 -2.84(14) ?
C10 C11 C17 O1 -4.64(19) y
N2 C11 C17 O1 176.22(11) y
C10 C11 C17 C14 176.34(11) ?
N2 C11 C17 C14 -2.80(14) ?
C15 C14 C17 O1 124.26(13) ?
C13 C14 C17 O1 -119.44(13) ?
C15 C14 C17 C11 -56.72(13) ?
C13 C14 C17 C11 59.59(13) ?
C2 N1 C18 C19 -85.00(14) ?
C9 N1 C18 C19 87.89(14) ?
N1 C18 C19 C24 -146.12(11) ?
N1 C18 C19 C20 36.84(16) ?
C24 C19 C20 C21 -0.35(18) ?
C18 C19 C20 C21 176.68(11) ?
C19 C20 C21 C22 -0.60(19) ?
C20 C21 C22 C23 0.78(19) ?
C21 C22 C23 C24 0.00(19) ?
C22 C23 C24 C19 -0.96(19) ?
C20 C19 C24 C23 1.13(18) ?
C18 C19 C24 C23 -176.01(11) ?
