#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/69/2226996.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_2226996
loop_
_publ_author_name
'Wang, Kaitong'
'Yuan, Jingkun'
'Chen, Guisheng'
'Chen, Qian'
'Wu, Huilu'
_publ_section_title
;
 Dibromido[1,1'-dibenzyl-2,2'-(sulfanediyldimethylene)di-1H-benzimidazole]cadmium(II)
 dimethylformamide solvate
;
_journal_coeditor_code           LH5084
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m993
_journal_paper_doi               10.1107/S1600536810028448
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cd Br2 (C30 H26 N4 S)], C3 H7 N O'
_chemical_formula_moiety         'C30 H26 Br2 Cd N4 S, C3 H7 N O'
_chemical_formula_sum            'C33 H33 Br2 Cd N5 O S'
_chemical_formula_weight         819.92
_chemical_name_systematic
;
Dibromido[1,1'-dibenzyl-2,2'-(sulfanediyldimethylene)di-1H-
benzimidazole]cadmium(II) dimethylformamide solvate
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.0290(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7437(8)
_cell_length_b                   16.7792(14)
_cell_length_c                   10.5931(9)
_cell_measurement_reflns_used    3975
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.22
_cell_volume                     1627.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_diffrn_measurement_method       'ω scans'
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9062
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    3.226
_exptl_absorpt_correction_T_max  0.4653
_exptl_absorpt_correction_T_min  0.3897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.636
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0291
_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)+(0.0374P)²+0.7961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0769
_reflns_number_gt                2742
_reflns_number_total             3305
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5084.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2226996
_cod_database_fobs_code          2226996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.53761(5) 0.2500 0.42042(5) 0.05529(15) Uani d S 1 . .
Br Br2 0.95622(6) 0.2500 0.72708(5) 0.05828(15) Uani d S 1 . .
C C1 1.0172(3) 0.16482(17) 0.2726(3) 0.0434(7) Uani d . 1 . .
H H1A 0.9562 0.1832 0.1844 0.052 Uiso calc R 1 . .
H H1B 1.1010 0.1377 0.2630 0.052 Uiso calc R 1 . .
C C2 0.9329(3) 0.10786(16) 0.3253(3) 0.0343(6) Uani d . 1 . .
C C3 0.9688(3) -0.01196(18) 0.1929(3) 0.0410(7) Uani d . 1 . .
H H3A 1.0153 -0.0620 0.2295 0.049 Uiso calc R 1 . .
H H3B 1.0400 0.0207 0.1714 0.049 Uiso calc R 1 . .
C C4 0.8399(3) -0.02804(19) 0.0656(3) 0.0444(7) Uani d . 1 . .
C C5 0.7349(5) 0.0278(3) 0.0121(4) 0.0949(16) Uani d . 1 . .
H H5 0.7429 0.0777 0.0523 0.114 Uiso calc R 1 . .
C C6 0.6156(6) 0.0109(4) -0.1025(5) 0.117(2) Uani d . 1 . .
H H6 0.5439 0.0493 -0.1376 0.140 Uiso calc R 1 . .
C C7 0.6033(5) -0.0607(3) -0.1629(4) 0.0825(13) Uani d . 1 . .
H H7 0.5234 -0.0716 -0.2395 0.099 Uiso calc R 1 . .
C C8 0.7068(5) -0.1163(3) -0.1119(3) 0.0691(11) Uani d . 1 . .
H H8 0.6985 -0.1656 -0.1539 0.083 Uiso calc R 1 . .
C C9 0.8260(4) -0.1008(2) 0.0029(3) 0.0545(8) Uani d . 1 . .
H H9 0.8967 -0.1398 0.0376 0.065 Uiso calc R 1 . .
C C10 0.8378(3) -0.00630(16) 0.3597(3) 0.0343(6) Uani d . 1 . .
C C11 0.7924(3) -0.08440(17) 0.3631(3) 0.0432(7) Uani d . 1 . .
H H11 0.8186 -0.1248 0.3157 0.052 Uiso calc R 1 . .
C C12 0.7067(3) -0.09879(19) 0.4403(3) 0.0491(7) Uani d . 1 . .
H H12 0.6721 -0.1501 0.4436 0.059 Uiso calc R 1 . .
C C13 0.6703(3) -0.03818(19) 0.5139(3) 0.0468(7) Uani d . 1 . .
H H13 0.6136 -0.0506 0.5662 0.056 Uiso calc R 1 . .
C C14 0.7157(3) 0.03915(18) 0.5110(3) 0.0421(7) Uani d . 1 . .
H H14 0.6912 0.0791 0.5603 0.051 Uiso calc R 1 . .
C C15 0.8005(3) 0.05523(17) 0.4308(3) 0.0351(6) Uani d . 1 . .
C C16 0.6054(6) 0.2500 1.0757(6) 0.0683(14) Uani d S 1 . .
H H16 0.5334 0.2500 1.1148 0.082 Uiso calc SR 1 . .
C C17 0.4073(8) 0.2500 0.8662(7) 0.111(3) Uani d S 1 . .
H H17A 0.3912 0.2763 0.7819 0.166 Uiso calc PR 0.50 . .
H H17B 0.3553 0.2776 0.9152 0.166 Uiso calc PR 0.50 . .
H H17C 0.3728 0.1961 0.8502 0.166 Uiso calc PR 0.50 . .
C C18 0.6637(11) 0.2500 0.8761(10) 0.133(3) Uani d S 1 . .
H H18A 0.6547 0.2014 0.8260 0.199 Uiso calc PR 0.50 . .
H H18B 0.7607 0.2540 0.9405 0.199 Uiso calc PR 0.50 . .
H H18C 0.6452 0.2946 0.8158 0.199 Uiso calc PR 0.50 . .
Cd Cd1 0.81788(3) 0.2500 0.46873(3) 0.04091(11) Uani d S 1 . .
N N1 0.8612(2) 0.12589(13) 0.4073(2) 0.0359(5) Uani d . 1 . .
N N2 0.9223(2) 0.02893(13) 0.2940(2) 0.0355(5) Uani d . 1 . .
N N3 0.5618(5) 0.2500 0.9435(5) 0.0682(12) Uani d S 1 . .
O O1 0.7309(5) 0.2500 1.1506(5) 0.1167(18) Uani d S 1 . .
S S1 1.07918(11) 0.2500 0.38353(10) 0.0414(2) Uani d S 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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
C2 C1 S1 . . 111.48(19) ?
C2 C1 H1A . . 109.3 ?
S1 C1 H1A . . 109.3 ?
C2 C1 H1B . . 109.3 ?
S1 C1 H1B . . 109.3 ?
H1A C1 H1B . . 108.0 ?
N1 C2 N2 . . 111.7(2) ?
N1 C2 C1 . . 125.7(2) ?
N2 C2 C1 . . 122.6(2) ?
N2 C3 C4 . . 111.3(2) ?
N2 C3 H3A . . 109.4 ?
C4 C3 H3A . . 109.4 ?
N2 C3 H3B . . 109.4 ?
C4 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
C5 C4 C9 . . 118.4(3) ?
C5 C4 C3 . . 121.5(3) ?
C9 C4 C3 . . 120.1(3) ?
C4 C5 C6 . . 120.4(4) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C7 C6 C5 . . 120.6(5) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C8 C7 C6 . . 119.7(4) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C7 C8 C9 . . 120.6(4) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C4 C9 C8 . . 120.3(4) ?
C4 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
N2 C10 C11 . . 131.9(3) ?
N2 C10 C15 . . 105.4(2) ?
C11 C10 C15 . . 122.7(3) ?
C12 C11 C10 . . 116.4(3) ?
C12 C11 H11 . . 121.8 ?
C10 C11 H11 . . 121.8 ?
C11 C12 C13 . . 121.7(3) ?
C11 C12 H12 . . 119.2 ?
C13 C12 H12 . . 119.2 ?
C14 C13 C12 . . 121.9(3) ?
C14 C13 H13 . . 119.1 ?
C12 C13 H13 . . 119.1 ?
C13 C14 C15 . . 117.2(3) ?
C13 C14 H14 . . 121.4 ?
C15 C14 H14 . . 121.4 ?
N1 C15 C10 . . 109.2(2) ?
N1 C15 C14 . . 130.7(3) ?
C10 C15 C14 . . 120.1(3) ?
O1 C16 N3 . . 125.8(6) ?
O1 C16 H16 . . 117.1 ?
N3 C16 H16 . . 117.1 ?
N3 C17 H17A . . 109.5 ?
N3 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N3 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N3 C18 H18A . . 109.5 ?
N3 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N3 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N1 Cd1 N1 . 4_565 133.74(11) ?
N1 Cd1 Br1 . . 103.31(6) ?
N1 Cd1 Br1 4_565 . 103.31(6) ?
N1 Cd1 Br2 . . 102.82(6) ?
N1 Cd1 Br2 4_565 . 102.82(6) ?
Br1 Cd1 Br2 . . 109.732(19) ?
N1 Cd1 S1 . . 69.50(5) ?
N1 Cd1 S1 4_565 . 69.50(5) ?
Br1 Cd1 S1 . . 152.80(3) ?
Br2 Cd1 S1 . . 97.46(3) ?
C2 N1 C15 . . 106.0(2) ?
C2 N1 Cd1 . . 126.29(18) ?
C15 N1 Cd1 . . 127.02(17) ?
C2 N2 C10 . . 107.6(2) ?
C2 N2 C3 . . 128.0(2) ?
C10 N2 C3 . . 123.7(2) ?
C16 N3 C18 . . 120.8(6) ?
C16 N3 C17 . . 119.8(5) ?
C18 N3 C17 . . 119.4(6) ?
C1 S1 C1 4_565 . 103.7(2) ?
C1 S1 Cd1 4_565 . 93.83(10) ?
C1 S1 Cd1 . . 93.83(10) ?
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
Br1 Cd1 . 2.6004(6) ?
Br2 Cd1 . 2.6038(6) ?
C1 C2 . 1.488(4) ?
C1 S1 . 1.817(3) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 N1 . 1.322(3) ?
C2 N2 . 1.360(3) ?
C3 N2 . 1.468(3) ?
C3 C4 . 1.519(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.360(5) ?
C4 C9 . 1.374(4) ?
C5 C6 . 1.393(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.347(7) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.344(6) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.389(5) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 N2 . 1.380(3) ?
C10 C11 . 1.387(4) ?
C10 C15 . 1.397(4) ?
C11 C12 . 1.376(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.399(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.375(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.399(4) ?
C14 H14 . 0.9300 ?
C15 N1 . 1.385(3) ?
C16 O1 . 1.208(7) ?
C16 N3 . 1.316(7) ?
C16 H16 . 0.9300 ?
C17 N3 . 1.446(8) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 N3 . 1.408(9) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
Cd1 N1 . 2.264(2) ?
Cd1 N1 4_565 2.264(2) ?
Cd1 S1 . 2.9784(11) ?
S1 C1 4_565 1.817(3) ?
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
C1 H1A O1 1_554 0.97 2.38 3.004(5) 121.6
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
S1 C1 C2 N1 . . . . 25.0(4) ?
S1 C1 C2 N2 . . . . -154.3(2) ?
N2 C3 C4 C5 . . . . 42.8(5) ?
N2 C3 C4 C9 . . . . -136.2(3) ?
C9 C4 C5 C6 . . . . 0.8(7) ?
C3 C4 C5 C6 . . . . -178.2(5) ?
C4 C5 C6 C7 . . . . -0.8(9) ?
C5 C6 C7 C8 . . . . 0.2(9) ?
C6 C7 C8 C9 . . . . 0.4(7) ?
C5 C4 C9 C8 . . . . -0.3(5) ?
C3 C4 C9 C8 . . . . 178.7(3) ?
C7 C8 C9 C4 . . . . -0.3(5) ?
N2 C10 C11 C12 . . . . -179.7(3) ?
C15 C10 C11 C12 . . . . 0.4(4) ?
C10 C11 C12 C13 . . . . -1.4(4) ?
C11 C12 C13 C14 . . . . 1.2(5) ?
C12 C13 C14 C15 . . . . 0.1(4) ?
N2 C10 C15 N1 . . . . 0.3(3) ?
C11 C10 C15 N1 . . . . -179.8(2) ?
N2 C10 C15 C14 . . . . -179.0(2) ?
C11 C10 C15 C14 . . . . 0.9(4) ?
C13 C14 C15 N1 . . . . 179.8(3) ?
C13 C14 C15 C10 . . . . -1.1(4) ?
N2 C2 N1 C15 . . . . 0.0(3) ?
C1 C2 N1 C15 . . . . -179.5(3) ?
N2 C2 N1 Cd1 . . . . -171.33(16) ?
C1 C2 N1 Cd1 . . . . 9.2(4) ?
C10 C15 N1 C2 . . . . -0.2(3) ?
C14 C15 N1 C2 . . . . 179.0(3) ?
C10 C15 N1 Cd1 . . . . 171.06(17) ?
C14 C15 N1 Cd1 . . . . -9.8(4) ?
N1 Cd1 N1 C2 4_565 . . . 5.0(3) ?
Br1 Cd1 N1 C2 . . . . 128.6(2) ?
Br2 Cd1 N1 C2 . . . . -117.2(2) ?
S1 Cd1 N1 C2 . . . . -23.9(2) ?
N1 Cd1 N1 C15 4_565 . . . -164.51(14) ?
Br1 Cd1 N1 C15 . . . . -40.9(2) ?
Br2 Cd1 N1 C15 . . . . 73.3(2) ?
S1 Cd1 N1 C15 . . . . 166.6(2) ?
N1 C2 N2 C10 . . . . 0.2(3) ?
C1 C2 N2 C10 . . . . 179.7(2) ?
N1 C2 N2 C3 . . . . 170.8(2) ?
C1 C2 N2 C3 . . . . -9.7(4) ?
C11 C10 N2 C2 . . . . 179.8(3) ?
C15 C10 N2 C2 . . . . -0.3(3) ?
C11 C10 N2 C3 . . . . 8.7(4) ?
C15 C10 N2 C3 . . . . -171.4(2) ?
C4 C3 N2 C2 . . . . -100.7(3) ?
C4 C3 N2 C10 . . . . 68.5(3) ?
O1 C16 N3 C18 . . . . 0.000(6) ?
O1 C16 N3 C17 . . . . 180.000(4) ?
C2 C1 S1 C1 . . . 4_565 -128.05(17) ?
C2 C1 S1 Cd1 . . . . -33.2(2) ?
N1 Cd1 S1 C1 . . . 4_565 131.08(12) ?
N1 Cd1 S1 C1 4_565 . . 4_565 -27.04(12) ?
Br1 Cd1 S1 C1 . . . 4_565 52.02(10) ?
Br2 Cd1 S1 C1 . . . 4_565 -127.98(10) ?
N1 Cd1 S1 C1 . . . . 27.03(12) ?
N1 Cd1 S1 C1 4_565 . . . -131.08(12) ?
Br1 Cd1 S1 C1 . . . . -52.02(10) ?
Br2 Cd1 S1 C1 . . . . 127.98(10) ?
