#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/74/2207468.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_2207468
loop_
_publ_author_name
'K. Ravikumar'
'B. Sridhar'
'M. Mahesh'
'V. V. Narayana Reddy'
_publ_section_title
;
 6-[(Z)-Benzylidene]-2,3-diphenyl-2-azabicyclo[2.2.2]octan-5-one
;
_journal_coeditor_code           CF2002
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4198
_journal_page_last               o4199
_journal_paper_doi               10.1107/S1600536805037530
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C26 H23 N O'
_chemical_formula_moiety         'C26 H23 N O'
_chemical_formula_sum            'C26 H23 N O'
_chemical_formula_weight         365.45
_chemical_name_systematic
;
6-[(Z)-Benzylidene]-2,3-diphenyl-2-azabicyclo[2.2.2]octan-5-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.154(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1554(9)
_cell_length_b                   16.5088(15)
_cell_length_c                   11.7903(11)
_cell_measurement_reflns_used    3275
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.35
_cell_measurement_theta_min      2.37
_cell_volume                     1961.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'SHELXTL/PC (Sheldrick, 1990) and MERCURY (Bruno et al.,  2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18504
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0683
_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)+(0.0509P)²+0.6492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                2759
_reflns_number_total             3437
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf2002.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207468
_cod_database_fobs_code          2207468
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'
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_type_symbol
C1 0.2912(2) 0.25311(14) 0.27571(18) 0.0406(6) Uani d . 1 C
H1 0.2210 0.2923 0.2511 0.049 Uiso calc R 1 H
C3 0.3342(2) 0.12064(13) 0.37012(19) 0.0420(6) Uani d . 1 C
H3 0.3407 0.1137 0.4532 0.050 Uiso calc R 1 H
C4 0.4709(2) 0.14989(15) 0.3423(2) 0.0464(6) Uani d . 1 C
H4 0.5401 0.1106 0.3694 0.056 Uiso calc R 1 H
C5 0.4990(2) 0.23061(15) 0.3999(2) 0.0468(6) Uani d . 1 C
C6 0.4010(2) 0.29321(14) 0.35494(18) 0.0405(6) Uani d . 1 C
C7 0.3481(3) 0.21810(16) 0.1722(2) 0.0523(7) Uani d . 1 C
H7A 0.3767 0.2617 0.1259 0.063 Uiso calc R 1 H
H7B 0.2803 0.1872 0.1257 0.063 Uiso calc R 1 H
C8 0.4662(3) 0.16306(16) 0.2131(2) 0.0554(7) Uani d . 1 C
H8A 0.4564 0.1115 0.1736 0.067 Uiso calc R 1 H
H8B 0.5480 0.1880 0.1964 0.067 Uiso calc R 1 H
C9 0.1419(2) 0.20103(14) 0.41199(18) 0.0402(5) Uani d . 1 C
C10 0.0935(2) 0.13700(16) 0.4720(2) 0.0513(6) Uani d . 1 C
H10 0.1250 0.0848 0.4628 0.062 Uiso calc R 1 H
C11 -0.0009(3) 0.15029(18) 0.5451(2) 0.0636(8) Uani d . 1 C
H11 -0.0328 0.1068 0.5836 0.076 Uiso calc R 1 H
C12 -0.0479(3) 0.2266(2) 0.5615(3) 0.0716(9) Uani d . 1 C
H12 -0.1107 0.2353 0.6112 0.086 Uiso calc R 1 H
C13 -0.0001(3) 0.29031(19) 0.5025(3) 0.0692(8) Uani d . 1 C
H13 -0.0309 0.3425 0.5132 0.083 Uiso calc R 1 H
C14 0.0925(2) 0.27782(16) 0.4282(2) 0.0520(7) Uani d . 1 C
H14 0.1221 0.3215 0.3885 0.062 Uiso calc R 1 H
C15 0.2940(2) 0.03950(15) 0.31577(19) 0.0449(6) Uani d . 1 C
C16 0.1857(3) 0.03093(16) 0.2337(2) 0.0578(7) Uani d . 1 C
H16 0.1355 0.0762 0.2094 0.069 Uiso calc R 1 H
C17 0.1506(3) -0.04382(18) 0.1870(2) 0.0688(8) Uani d . 1 C
H17 0.0767 -0.0484 0.1323 0.083 Uiso calc R 1 H
C18 0.2234(3) -0.11109(18) 0.2204(3) 0.0677(8) Uani d . 1 C
H18 0.2007 -0.1612 0.1875 0.081 Uiso calc R 1 H
C19 0.3299(3) -0.10405(18) 0.3029(3) 0.0724(9) Uani d . 1 C
H19 0.3792 -0.1497 0.3273 0.087 Uiso calc R 1 H
C20 0.3643(3) -0.02953(16) 0.3496(2) 0.0644(8) Uani d . 1 C
H20 0.4371 -0.0256 0.4056 0.077 Uiso calc R 1 H
C21 0.4142(2) 0.37012(15) 0.3876(2) 0.0465(6) Uani d . 1 C
H21 0.4846 0.3804 0.4441 0.056 Uiso calc R 1 H
C22 0.3352(2) 0.44092(14) 0.3484(2) 0.0455(6) Uani d . 1 C
C23 0.2799(3) 0.45047(16) 0.2347(2) 0.0583(7) Uani d . 1 C
H23 0.2905 0.4100 0.1818 0.070 Uiso calc R 1 H
C24 0.2098(3) 0.51933(18) 0.2006(3) 0.0696(8) Uani d . 1 C
H24 0.1728 0.5248 0.1248 0.084 Uiso calc R 1 H
C25 0.1939(3) 0.58008(18) 0.2769(3) 0.0689(8) Uani d . 1 C
H25 0.1463 0.6265 0.2530 0.083 Uiso calc R 1 H
C26 0.2485(3) 0.57211(18) 0.3887(3) 0.0651(8) Uani d . 1 C
H26 0.2385 0.6133 0.4407 0.078 Uiso calc R 1 H
C27 0.3180(3) 0.50326(16) 0.4240(2) 0.0546(7) Uani d . 1 C
H27 0.3543 0.4984 0.5001 0.066 Uiso calc R 1 H
N2 0.23783(18) 0.18577(11) 0.33854(15) 0.0404(5) Uani d . 1 N
O28 0.59236(18) 0.24337(12) 0.47327(17) 0.0696(6) Uani d . 1 O
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'
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
N2 C1 C6 107.93(17) ?
N2 C1 C7 108.36(19) ?
C6 C1 C7 109.62(19) ?
N2 C1 H1 110.3 ?
C6 C1 H1 110.3 ?
C7 C1 H1 110.3 ?
N2 C3 C15 113.74(18) ?
N2 C3 C4 107.79(18) ?
C15 C3 C4 112.84(19) ?
N2 C3 H3 107.4 ?
C15 C3 H3 107.4 ?
C4 C3 H3 107.4 ?
C5 C4 C8 107.6(2) ?
C5 C4 C3 107.82(18) ?
C8 C4 C3 109.7(2) ?
C5 C4 H4 110.5 ?
C8 C4 H4 110.5 ?
C3 C4 H4 110.5 ?
O28 C5 C6 124.0(2) ?
O28 C5 C4 124.0(2) ?
C6 C5 C4 111.9(2) ?
C21 C6 C5 121.5(2) ?
C21 C6 C1 129.5(2) y
C5 C6 C1 109.0(2) ?
C1 C7 C8 109.38(19) ?
C1 C7 H7A 109.8 ?
C8 C7 H7A 109.8 ?
C1 C7 H7B 109.8 ?
C8 C7 H7B 109.8 ?
H7A C7 H7B 108.2 ?
C4 C8 C7 108.84(19) ?
C4 C8 H8A 109.9 ?
C7 C8 H8A 109.9 ?
C4 C8 H8B 109.9 ?
C7 C8 H8B 109.9 ?
H8A C8 H8B 108.3 ?
C14 C9 C10 117.8(2) ?
C14 C9 N2 122.7(2) ?
C10 C9 N2 119.5(2) ?
C11 C10 C9 120.7(2) ?
C11 C10 H10 119.6 ?
C9 C10 H10 119.6 ?
C12 C11 C10 121.0(3) ?
C12 C11 H11 119.5 ?
C10 C11 H11 119.5 ?
C11 C12 C13 118.6(3) ?
C11 C12 H12 120.7 ?
C13 C12 H12 120.7 ?
C14 C13 C12 121.1(3) ?
C14 C13 H13 119.5 ?
C12 C13 H13 119.5 ?
C13 C14 C9 120.8(3) ?
C13 C14 H14 119.6 ?
C9 C14 H14 119.6 ?
C20 C15 C16 117.3(2) ?
C20 C15 C3 120.3(2) ?
C16 C15 C3 122.4(2) ?
C15 C16 C17 121.0(3) ?
C15 C16 H16 119.5 ?
C17 C16 H16 119.5 ?
C18 C17 C16 120.6(3) ?
C18 C17 H17 119.7 ?
C16 C17 H17 119.7 ?
C17 C18 C19 119.3(3) ?
C17 C18 H18 120.4 ?
C19 C18 H18 120.4 ?
C18 C19 C20 120.0(3) ?
C18 C19 H19 120.0 ?
C20 C19 H19 120.0 ?
C19 C20 C15 121.8(3) ?
C19 C20 H20 119.1 ?
C15 C20 H20 119.1 ?
C6 C21 C22 129.9(2) y
C6 C21 H21 115.1 ?
C22 C21 H21 115.1 ?
C27 C22 C23 117.8(2) ?
C27 C22 C21 119.9(2) ?
C23 C22 C21 122.3(2) ?
C24 C23 C22 120.4(3) ?
C24 C23 H23 119.8 ?
C22 C23 H23 119.8 ?
C25 C24 C23 120.8(3) ?
C25 C24 H24 119.6 ?
C23 C24 H24 119.6 ?
C24 C25 C26 119.6(3) ?
C24 C25 H25 120.2 ?
C26 C25 H25 120.2 ?
C25 C26 C27 120.1(3) ?
C25 C26 H26 119.9 ?
C27 C26 H26 119.9 ?
C26 C27 C22 121.3(3) ?
C26 C27 H27 119.4 ?
C22 C27 H27 119.4 ?
C9 N2 C3 117.77(18) ?
C9 N2 C1 120.04(18) ?
C3 N2 C1 113.79(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 1.476(3) ?
C1 C6 1.515(3) ?
C1 C7 1.527(3) ?
C1 H1 0.980 ?
C3 N2 1.470(3) ?
C3 C15 1.519(3) ?
C3 C4 1.544(3) ?
C3 H3 0.980 ?
C4 C5 1.506(3) ?
C4 C8 1.534(3) ?
C4 H4 0.980 ?
C5 O28 1.220(3) y
C5 C6 1.486(3) ?
C6 C21 1.329(3) y
C7 C8 1.534(4) ?
C7 H7A 0.970 ?
C7 H7B 0.970 ?
C8 H8A 0.970 ?
C8 H8B 0.970 ?
C9 C14 1.385(3) ?
C9 C10 1.395(3) ?
C9 N2 1.404(3) ?
C10 C11 1.383(4) ?
C10 H10 0.930 ?
C11 C12 1.369(4) ?
C11 H11 0.930 ?
C12 C13 1.382(4) ?
C12 H12 0.930 ?
C13 C14 1.379(4) ?
C13 H13 0.930 ?
C14 H14 0.930 ?
C15 C20 1.377(3) ?
C15 C16 1.379(3) ?
C16 C17 1.380(4) ?
C16 H16 0.930 ?
C17 C18 1.365(4) ?
C17 H17 0.930 ?
C18 C19 1.366(4) ?
C18 H18 0.930 ?
C19 C20 1.375(4) ?
C19 H19 0.930 ?
C20 H20 0.930 ?
C21 C22 1.460(3) ?
C21 H21 0.930 ?
C22 C27 1.387(3) ?
C22 C23 1.396(3) ?
C23 C24 1.374(4) ?
C23 H23 0.930 ?
C24 C25 1.371(4) ?
C24 H24 0.930 ?
C25 C26 1.371(4) ?
C25 H25 0.930 ?
C26 C27 1.375(4) ?
C26 H26 0.930 ?
C27 H27 0.930 ?
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
N2 C3 C4 C5 53.2(2)
C15 C3 C4 C5 179.59(19)
N2 C3 C4 C8 -63.8(2)
C15 C3 C4 C8 62.7(2)
C8 C4 C5 O28 -123.6(3)
C3 C4 C5 O28 118.2(3)
C8 C4 C5 C6 55.3(2)
C3 C4 C5 C6 -62.9(2)
O28 C5 C6 C21 4.5(4)
C4 C5 C6 C21 -174.4(2)
O28 C5 C6 C1 -173.4(2)
C4 C5 C6 C1 7.7(3)
N2 C1 C6 C21 -123.8(3)
C7 C1 C6 C21 118.4(3)
N2 C1 C6 C5 53.8(2)
C7 C1 C6 C5 -64.0(2)
N2 C1 C7 C8 -64.4(2)
C6 C1 C7 C8 53.1(3)
C5 C4 C8 C7 -64.8(3)
C3 C4 C8 C7 52.2(3)
C1 C7 C8 C4 10.1(3)
C14 C9 C10 C11 0.1(4)
N2 C9 C10 C11 179.9(2)
C9 C10 C11 C12 -0.8(4)
C10 C11 C12 C13 0.6(5)
C11 C12 C13 C14 0.3(5)
C12 C13 C14 C9 -1.1(4)
C10 C9 C14 C13 0.9(4)
N2 C9 C14 C13 -179.0(2)
N2 C3 C15 C20 -170.8(2)
C4 C3 C15 C20 66.0(3)
N2 C3 C15 C16 7.7(3)
C4 C3 C15 C16 -115.5(3)
C20 C15 C16 C17 -0.6(4)
C3 C15 C16 C17 -179.1(2)
C15 C16 C17 C18 -0.6(4)
C16 C17 C18 C19 1.5(5)
C17 C18 C19 C20 -1.2(5)
C18 C19 C20 C15 0.0(5)
C16 C15 C20 C19 0.9(4)
C3 C15 C20 C19 179.5(3)
C5 C6 C21 C22 175.3(2)
C1 C6 C21 C22 -7.3(4)
C6 C21 C22 C27 147.3(3)
C6 C21 C22 C23 -35.7(4)
C27 C22 C23 C24 -0.7(4)
C21 C22 C23 C24 -177.8(2)
C22 C23 C24 C25 0.6(4)
C23 C24 C25 C26 0.0(5)
C24 C25 C26 C27 -0.5(4)
C25 C26 C27 C22 0.3(4)
C23 C22 C27 C26 0.3(4)
C21 C22 C27 C26 177.5(2)
C14 C9 N2 C3 146.9(2)
C10 C9 N2 C3 -33.0(3)
C14 C9 N2 C1 0.7(3)
C10 C9 N2 C1 -179.2(2)
C15 C3 N2 C9 94.3(2)
C4 C3 N2 C9 -139.84(19)
C15 C3 N2 C1 -117.5(2)
C4 C3 N2 C1 8.4(2)
C6 C1 N2 C9 83.1(2)
C7 C1 N2 C9 -158.28(19)
C6 C1 N2 C3 -64.4(2)
C7 C1 N2 C3 54.2(2)
