#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/09/2230915.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_2230915
loop_
_publ_author_name
'Zhang, Xiao-Wen'
'Fan, Ting'
_publ_section_title
;
 6-Phenyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl
 perchlorate
;
_journal_coeditor_code           XU5208
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m875
_journal_paper_doi               10.1107/S1600536811021039
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Bi (C20 H17 N) (Cl O4)]'
_chemical_formula_moiety         'C20 H17 Bi Cl N O4'
_chemical_formula_sum            'C20 H17 Bi Cl N O4'
_chemical_formula_weight         579.78
_chemical_name_systematic
;
6-Phenyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl
perchlorate
;
_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                 107.590(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0635(10)
_cell_length_b                   14.0755(12)
_cell_length_c                   11.5121(10)
_cell_measurement_reflns_used    2936
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.7
_cell_volume                     1863.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1658
_diffrn_reflns_av_sigmaI/netI    0.1191
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9267
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    9.632
_exptl_absorpt_correction_T_max  0.145
_exptl_absorpt_correction_T_min  0.100
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.067
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.203
_refine_diff_density_max         4.891
_refine_diff_density_min         -4.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0816P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1629
_reflns_number_gt                2585
_reflns_number_total             3279
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5208.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230915
_cod_database_fobs_code          2230915
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_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
Bi Bi 0.74646(4) 0.77309(3) 0.84604(4) 0.0321(2) Uani d . 1 1 . .
Cl Cl1 0.7240(3) 1.0213(2) 0.8825(3) 0.0378(7) Uani d . 1 1 . .
N N1 0.7225(7) 0.6171(8) 0.7606(7) 0.033(2) Uani d . 1 1 . .
O O1 0.7940(9) 0.9494(7) 0.8480(10) 0.063(3) Uani d . 1 1 . .
O O2 0.6291(9) 0.9730(7) 0.9075(10) 0.069(3) Uani d . 1 1 . .
O O3 0.6836(10) 1.0854(8) 0.7850(10) 0.071(3) Uani d . 1 1 . .
O O4 0.7937(12) 1.0687(8) 0.9874(10) 0.086(4) Uani d . 1 1 . .
C C1 0.6226(11) 0.7895(8) 0.6574(11) 0.037(3) Uani d . 1 1 . .
C C2 0.6002(10) 0.8714(8) 0.5878(10) 0.034(3) Uani d . 1 1 . .
H H2 0.6373 0.9281 0.6181 0.041 Uiso calc R 1 1 . .
C C3 0.5204(11) 0.8671(9) 0.4706(11) 0.041(3) Uani d . 1 1 . .
H H3 0.5026 0.9222 0.4241 0.049 Uiso calc R 1 1 . .
C C4 0.4688(12) 0.7846(8) 0.4240(12) 0.042(3) Uani d . 1 1 . .
H H4 0.4163 0.7830 0.3459 0.051 Uiso calc R 1 1 . .
C C5 0.4949(11) 0.7005(9) 0.4943(11) 0.037(3) Uani d . 1 1 . .
H H5 0.4603 0.6435 0.4617 0.045 Uiso calc R 1 1 . .
C C6 0.5695(10) 0.7026(9) 0.6080(10) 0.033(3) Uani d . 1 1 . .
C C7 0.5996(10) 0.6133(8) 0.6827(9) 0.031(3) Uani d . 1 1 . .
H H7A 0.5489 0.6068 0.7335 0.037 Uiso calc R 1 1 . .
H H7B 0.5881 0.5586 0.6292 0.037 Uiso calc R 1 1 . .
C C8 0.8978(11) 0.7594(8) 0.7776(11) 0.030(3) Uani d . 1 1 . .
C C9 0.9896(11) 0.8252(10) 0.7942(12) 0.047(3) Uani d . 1 1 . .
H H9 0.9914 0.8787 0.8421 0.056 Uiso calc R 1 1 . .
C C10 1.0741(11) 0.8122(10) 0.7424(14) 0.051(4) Uani d . 1 1 . .
H H10 1.1337 0.8565 0.7542 0.062 Uiso calc R 1 1 . .
C C11 1.0723(14) 0.7321(10) 0.6709(16) 0.055(4) Uani d . 1 1 . .
H H11 1.1291 0.7246 0.6321 0.066 Uiso calc R 1 1 . .
C C12 0.9893(10) 0.6651(9) 0.6570(11) 0.038(3) Uani d . 1 1 . .
H H12 0.9919 0.6101 0.6132 0.045 Uiso calc R 1 1 . .
C C13 0.8986(9) 0.6785(8) 0.7091(9) 0.030(2) Uani d . 1 1 . .
C C14 0.8015(10) 0.6065(8) 0.6812(10) 0.033(3) Uani d . 1 1 . .
H H14A 0.8350 0.5433 0.6923 0.040 Uiso calc R 1 1 . .
H H14B 0.7555 0.6128 0.5965 0.040 Uiso calc R 1 1 . .
C C15 0.7472(9) 0.5399(9) 0.8534(10) 0.033(3) Uani d . 1 1 . .
C C16 0.6852(11) 0.4552(9) 0.8367(12) 0.041(3) Uani d . 1 1 . .
H H16 0.6240 0.4455 0.7659 0.049 Uiso calc R 1 1 . .
C C17 0.7139(13) 0.3865(10) 0.9238(14) 0.053(4) Uani d . 1 1 . .
H H17 0.6723 0.3298 0.9117 0.064 Uiso calc R 1 1 . .
C C18 0.8062(14) 0.4002(11) 1.0325(14) 0.058(4) Uani d . 1 1 . .
H H18 0.8251 0.3532 1.0919 0.069 Uiso calc R 1 1 . .
C C19 0.8671(14) 0.4831(12) 1.0489(13) 0.064(4) Uani d . 1 1 . .
H H19 0.9281 0.4920 1.1202 0.077 Uiso calc R 1 1 . .
C C20 0.8408(11) 0.5534(11) 0.9634(11) 0.050(3) Uani d . 1 1 . .
H H20 0.8833 0.6097 0.9763 0.060 Uiso calc R 1 1 . .
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'
F F 0.0171 0.0103 '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'
Bi Bi -4.1077 10.2566 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 Bi C1 . . 92.5(5) ?
C8 Bi N1 . . 77.4(4) ?
C1 Bi N1 . . 74.6(4) ?
C8 Bi O1 . . 83.1(4) ?
C1 Bi O1 . . 89.4(4) ?
N1 Bi O1 . . 154.0(3) ?
O3 Cl1 O4 . . 110.7(7) ?
O3 Cl1 O2 . . 111.0(7) ?
O4 Cl1 O2 . . 110.9(7) ?
O3 Cl1 O1 . . 108.6(7) ?
O4 Cl1 O1 . . 108.6(8) ?
O2 Cl1 O1 . . 106.9(6) ?
C7 N1 C15 . . 110.7(9) ?
C7 N1 C14 . . 109.2(8) ?
C15 N1 C14 . . 109.6(8) ?
C7 N1 Bi . . 104.8(7) ?
C15 N1 Bi . . 113.7(6) ?
C14 N1 Bi . . 108.6(7) ?
Cl1 O1 Bi . . 122.3(6) ?
C2 C1 C6 . . 120.1(12) ?
C2 C1 Bi . . 127.1(9) ?
C6 C1 Bi . . 112.7(8) ?
C1 C2 C3 . . 118.6(12) ?
C1 C2 H2 . . 120.7 ?
C3 C2 H2 . . 120.7 ?
C4 C3 C2 . . 121.3(12) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C3 C4 C5 . . 119.8(13) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C6 C5 C4 . . 120.4(12) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 119.8(12) ?
C5 C6 C7 . . 120.9(11) ?
C1 C6 C7 . . 119.3(11) ?
N1 C7 C6 . . 109.9(9) ?
N1 C7 H7A . . 109.7 ?
C6 C7 H7A . . 109.7 ?
N1 C7 H7B . . 109.7 ?
C6 C7 H7B . . 109.7 ?
H7A C7 H7B . . 108.2 ?
C13 C8 C9 . . 118.4(11) ?
C13 C8 Bi . . 115.1(8) ?
C9 C8 Bi . . 126.5(9) ?
C10 C9 C8 . . 121.5(13) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C9 C10 C11 . . 119.7(13) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C12 C11 C10 . . 120.9(13) ?
C12 C11 H11 . . 119.5 ?
C10 C11 H11 . . 119.5 ?
C11 C12 C13 . . 120.0(12) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C8 C13 C12 . . 119.4(11) ?
C8 C13 C14 . . 122.3(10) ?
C12 C13 C14 . . 118.2(10) ?
C13 C14 N1 . . 113.3(9) ?
C13 C14 H14A . . 108.9 ?
N1 C14 H14A . . 108.9 ?
C13 C14 H14B . . 108.9 ?
N1 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
C16 C15 C20 . . 119.0(11) ?
C16 C15 N1 . . 123.0(10) ?
C20 C15 N1 . . 118.0(11) ?
C17 C16 C15 . . 120.1(13) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C16 C17 C18 . . 120.8(14) ?
C16 C17 H17 . . 119.6 ?
C18 C17 H17 . . 119.6 ?
C19 C18 C17 . . 119.2(13) ?
C19 C18 H18 . . 120.4 ?
C17 C18 H18 . . 120.4 ?
C18 C19 C20 . . 121.6(15) ?
C18 C19 H19 . . 119.2 ?
C20 C19 H19 . . 119.2 ?
C19 C20 C15 . . 119.4(14) ?
C19 C20 H20 . . 120.3 ?
C15 C20 H20 . . 120.3 ?
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
Bi N1 . 2.387(10) y
Bi O1 . 2.546(10) y
Bi C1 . 2.245(13) y
Bi C8 . 2.204(12) y
Cl1 O3 . 1.407(10) ?
Cl1 O4 . 1.413(10) ?
Cl1 O2 . 1.434(10) ?
Cl1 O1 . 1.448(10) ?
N1 C7 . 1.484(13) ?
N1 C15 . 1.490(15) ?
N1 C14 . 1.514(12) ?
C1 C2 . 1.383(16) ?
C1 C6 . 1.418(17) ?
C2 C3 . 1.402(17) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.351(18) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.414(18) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.347(16) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.504(16) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C13 . 1.387(17) ?
C8 C9 . 1.411(17) ?
C9 C10 . 1.340(18) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.39(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.349(19) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.410(16) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.508(15) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.389(18) ?
C15 C20 . 1.432(16) ?
C16 C17 . 1.360(18) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.41(2) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.36(2) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.365(19) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
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
C4 H4 O3 3_676 0.93 2.46 3.137(17) 130
C14 H14B O2 4_575 0.97 2.55 3.398(16) 146
