#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/18/2231883.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_2231883
loop_
_publ_author_name
'Li, Hui'
'Jiang, Hongshi'
'Sun, Hong'
_publ_section_title
;
 Hexa-μ-chlorido-μ₄-oxido-tetrakis({1-[(pyridin-2-yl)methyl]-1H-benzimidazole-κN³}copper(II))
;
_journal_coeditor_code           HB6384
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1372
_journal_paper_doi               10.1107/S1600536811035252
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu4 Cl6 O (C13 H11 N3)4]'
_chemical_formula_moiety         'C52 H44 Cl6 Cu4 N12 O'
_chemical_formula_sum            'C52 H44 Cl6 Cu4 N12 O'
_chemical_formula_weight         1319.85
_chemical_name_systematic
;
Hexa-μ-chlorido-μ₄-oxido-tetrakis({1-[(pyridin-2-yl)methyl]-
1H-benzimidazole-κN³}copper(II))
;
_space_group_IT_number           82
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I -4'
_symmetry_space_group_name_H-M   'I -4'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.8532(12)
_cell_length_b                   13.8532(12)
_cell_length_c                   14.507(3)
_cell_measurement_reflns_used    3492
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.2503
_cell_measurement_theta_min      2.8081
_cell_volume                     2784.1(7)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_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      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7149
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_exptl_absorpt_coefficient_mu    1.845
_exptl_absorpt_correction_T_max  0.691
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.172
_refine_ls_abs_structure_details 'Flack (1983), 1172 Friedel pairs'
_refine_ls_abs_structure_Flack   0.005(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0280
_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)+(0.0286P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0623
_reflns_number_gt                2178
_reflns_number_total             2467
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6384.cif
_cod_data_source_block           I
_cod_original_cell_volume        2784.1(6)
_cod_database_code               2231883
_cod_database_fobs_code          2231883
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+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
Cu Cu1 0.42929(3) 0.41004(3) 0.07467(3) 0.03400(12) Uani d . 1 1
Cl Cl1 0.28847(6) 0.47255(6) -0.00384(7) 0.0473(2) Uani d . 1 1
Cl Cl2 0.5000 0.5000 0.20129(8) 0.0637(4) Uani d S 1 2
N N3 0.3550(2) 0.3189(2) 0.1515(2) 0.0412(7) Uani d . 1 1
C C1 0.3592(3) 0.2243(3) 0.1520(3) 0.0498(10) Uani d . 1 1
H H1 0.3992 0.1887 0.1133 0.060 Uiso calc R 1 1
C C2 0.2867(3) 0.3436(3) 0.2180(2) 0.0485(10) Uani d . 1 1
C C7 0.2518(3) 0.2588(3) 0.2595(3) 0.0533(10) Uani d . 1 1
N N2 0.2998(3) 0.1839(2) 0.2144(2) 0.0548(9) Uani d . 1 1
C C6 0.1844(3) 0.2627(4) 0.3322(3) 0.0736(15) Uani d . 1 1
H H6 0.1636 0.2068 0.3616 0.088 Uiso calc R 1 1
C C3 0.2513(3) 0.4325(3) 0.2461(3) 0.0663(13) Uani d . 1 1
H H3 0.2726 0.4892 0.2184 0.080 Uiso calc R 1 1
C C4 0.1837(4) 0.4350(4) 0.3161(4) 0.0844(16) Uani d . 1 1
H H4 0.1593 0.4940 0.3359 0.101 Uiso calc R 1 1
C C5 0.1515(4) 0.3495(5) 0.3574(4) 0.0899(18) Uani d . 1 1
H H5 0.1056 0.3532 0.4040 0.108 Uiso calc R 1 1
C C8 0.2900(4) 0.0806(3) 0.2368(3) 0.0755(15) Uani d . 1 1
H H8A 0.2343 0.0721 0.2764 0.091 Uiso calc R 1 1
H H8B 0.3465 0.0601 0.2711 0.091 Uiso calc R 1 1
O O1 0.5000 0.5000 0.0000 0.0292(9) Uani d S 1 4
C C9 0.2789(3) 0.0170(3) 0.1543(3) 0.0563(10) Uani d . 1 1
C C10 0.1944(4) -0.0195(4) 0.1286(4) 0.0846(16) Uani d . 1 1
H H10 0.1380 -0.0038 0.1600 0.102 Uiso calc R 1 1
N N1 0.3632(4) -0.0017(4) 0.1100(4) 0.1075(18) Uani d . 1 1
C C12 0.2815(9) -0.1018(5) 0.0115(5) 0.128(3) Uani d . 1 1
H H12 0.2863 -0.1449 -0.0374 0.154 Uiso calc R 1 1
C C11 0.1926(7) -0.0858(5) 0.0487(5) 0.116(2) Uani d . 1 1
H H11 0.1364 -0.1138 0.0261 0.139 Uiso calc R 1 1
C C13 0.3600(8) -0.0601(5) 0.0405(6) 0.140(4) Uani d . 1 1
H H13 0.4172 -0.0730 0.0093 0.168 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
O1 Cu1 N3 . . 179.14(9)
O1 Cu1 Cl1 . 4_655 85.68(3)
N3 Cu1 Cl1 . 4_655 95.10(9)
O1 Cu1 Cl1 . . 85.03(3)
N3 Cu1 Cl1 . . 94.25(9)
Cl1 Cu1 Cl1 4_655 . 120.483(17)
O1 Cu1 Cl2 . . 83.56(2)
N3 Cu1 Cl2 . . 96.40(9)
Cl1 Cu1 Cl2 4_655 . 117.17(3)
Cl1 Cu1 Cl2 . . 119.88(3)
Cu1 Cl1 Cu1 3_565 . 80.69(3)
Cu1 Cl2 Cu1 . 2_665 81.58(4)
C1 N3 C2 . . 105.8(3)
C1 N3 Cu1 . . 128.2(3)
C2 N3 Cu1 . . 126.0(2)
N3 C1 N2 . . 113.1(4)
N3 C1 H1 . . 123.5
N2 C1 H1 . . 123.5
C3 C2 N3 . . 131.4(3)
C3 C2 C7 . . 119.6(4)
N3 C2 C7 . . 108.9(4)
N2 C7 C2 . . 104.9(4)
N2 C7 C6 . . 134.1(4)
C2 C7 C6 . . 121.0(5)
C1 N2 C7 . . 107.4(3)
C1 N2 C8 . . 127.5(4)
C7 N2 C8 . . 125.1(4)
C5 C6 C7 . . 117.8(4)
C5 C6 H6 . . 121.1
C7 C6 H6 . . 121.1
C4 C3 C2 . . 118.6(4)
C4 C3 H3 . . 120.7
C2 C3 H3 . . 120.7
C3 C4 C5 . . 120.6(5)
C3 C4 H4 . . 119.7
C5 C4 H4 . . 119.7
C6 C5 C4 . . 122.3(5)
C6 C5 H5 . . 118.8
C4 C5 H5 . . 118.8
N2 C8 C9 . . 113.9(4)
N2 C8 H8A . . 108.8
C9 C8 H8A . . 108.8
N2 C8 H8B . . 108.8
C9 C8 H8B . . 108.8
H8A C8 H8B . . 107.7
Cu1 O1 Cu1 2_665 4_655 108.564(12)
Cu1 O1 Cu1 2_665 . 111.30(2)
Cu1 O1 Cu1 4_655 . 108.564(12)
Cu1 O1 Cu1 2_665 3_565 108.564(12)
Cu1 O1 Cu1 4_655 3_565 111.30(2)
Cu1 O1 Cu1 . 3_565 108.564(12)
C10 C9 N1 . . 123.5(5)
C10 C9 C8 . . 122.7(5)
N1 C9 C8 . . 113.8(5)
C9 C10 C11 . . 118.1(6)
C9 C10 H10 . . 121.0
C11 C10 H10 . . 121.0
C13 N1 C9 . . 117.3(7)
C13 C12 C11 . . 123.7(8)
C13 C12 H12 . . 118.1
C11 C12 H12 . . 118.1
C12 C11 C10 . . 113.3(7)
C12 C11 H11 . . 123.3
C10 C11 H11 . . 123.3
N1 C13 C12 . . 123.9(8)
N1 C13 H13 . . 118.0
C12 C13 H13 . . 118.0
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
Cu1 O1 . 1.9199(4) y
Cu1 N3 . 1.974(3) y
Cu1 Cl1 4_655 2.3961(10) y
Cu1 Cl1 . 2.4192(10) y
Cu1 Cl2 . 2.4263(10) y
Cl1 Cu1 3_565 2.3961(9) ?
Cl2 Cu1 2_665 2.4263(10) ?
N3 C1 . 1.313(4) ?
N3 C2 . 1.394(5) ?
C1 N2 . 1.345(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.386(6) ?
C2 C7 . 1.407(5) ?
C7 N2 . 1.395(6) ?
C7 C6 . 1.409(6) ?
N2 C8 . 1.474(5) ?
C6 C5 . 1.337(8) ?
C6 H6 . 0.9300 ?
C3 C4 . 1.382(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.400(7) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C8 C9 . 1.494(7) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
O1 Cu1 2_665 1.9199(4) ?
O1 Cu1 4_655 1.9199(4) ?
O1 Cu1 3_565 1.9199(4) ?
C9 C10 . 1.328(6) ?
C9 N1 . 1.358(6) ?
C10 C11 . 1.480(8) ?
C10 H10 . 0.9300 ?
N1 C13 . 1.293(9) ?
C12 C13 . 1.301(12) ?
C12 C11 . 1.362(10) ?
C12 H12 . 0.9300 ?
C11 H11 . 0.9300 ?
C13 H13 . 0.9300 ?
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_4
_geom_torsion
O1 Cu1 Cl1 Cu1 . 3_565 -1.10(2)
N3 Cu1 Cl1 Cu1 . 3_565 178.42(9)
Cl1 Cu1 Cl1 Cu1 4_655 3_565 -83.12(4)
Cl2 Cu1 Cl1 Cu1 . 3_565 78.54(4)
O1 Cu1 Cl2 Cu1 . 2_665 0.0
N3 Cu1 Cl2 Cu1 . 2_665 -179.13(9)
Cl1 Cu1 Cl2 Cu1 4_655 2_665 81.77(3)
Cl1 Cu1 Cl2 Cu1 . 2_665 -80.48(3)
O1 Cu1 N3 C1 . . 150(6)
Cl1 Cu1 N3 C1 4_655 . -4.5(3)
Cl1 Cu1 N3 C1 . . 116.6(3)
Cl2 Cu1 N3 C1 . . -122.7(3)
O1 Cu1 N3 C2 . . -31(6)
Cl1 Cu1 N3 C2 4_655 . 174.8(3)
Cl1 Cu1 N3 C2 . . -64.1(3)
Cl2 Cu1 N3 C2 . . 56.7(3)
C2 N3 C1 N2 . . -0.7(4)
Cu1 N3 C1 N2 . . 178.8(2)
C1 N3 C2 C3 . . -178.6(4)
Cu1 N3 C2 C3 . . 2.0(6)
C1 N3 C2 C7 . . 1.2(4)
Cu1 N3 C2 C7 . . -178.3(2)
C3 C2 C7 N2 . . 178.6(4)
N3 C2 C7 N2 . . -1.2(4)
C3 C2 C7 C6 . . -2.8(6)
N3 C2 C7 C6 . . 177.4(4)
N3 C1 N2 C7 . . -0.1(4)
N3 C1 N2 C8 . . -176.6(4)
C2 C7 N2 C1 . . 0.8(4)
C6 C7 N2 C1 . . -177.6(5)
C2 C7 N2 C8 . . 177.4(4)
C6 C7 N2 C8 . . -1.0(8)
N2 C7 C6 C5 . . -178.9(5)
C2 C7 C6 C5 . . 3.0(7)
N3 C2 C3 C4 . . -178.9(4)
C7 C2 C3 C4 . . 1.4(7)
C2 C3 C4 C5 . . -0.2(8)
C7 C6 C5 C4 . . -1.8(9)
C3 C4 C5 C6 . . 0.5(9)
C1 N2 C8 C9 . . -48.8(6)
C7 N2 C8 C9 . . 135.3(4)
N3 Cu1 O1 Cu1 . 2_665 88(6)
Cl1 Cu1 O1 Cu1 4_655 2_665 -117.99(3)
Cl1 Cu1 O1 Cu1 . 2_665 120.87(3)
Cl2 Cu1 O1 Cu1 . 2_665 0.0
N3 Cu1 O1 Cu1 . 4_655 -153(6)
Cl1 Cu1 O1 Cu1 4_655 4_655 1.44(3)
Cl1 Cu1 O1 Cu1 . 4_655 -119.70(3)
Cl2 Cu1 O1 Cu1 . 4_655 119.434(8)
N3 Cu1 O1 Cu1 . 3_565 -32(6)
Cl1 Cu1 O1 Cu1 4_655 3_565 122.58(3)
Cl1 Cu1 O1 Cu1 . 3_565 1.43(3)
Cl2 Cu1 O1 Cu1 . 3_565 -119.434(8)
N2 C8 C9 C10 . . -102.8(6)
N2 C8 C9 N1 . . 78.9(5)
N1 C9 C10 C11 . . 1.4(7)
C8 C9 C10 C11 . . -176.8(4)
C10 C9 N1 C13 . . -1.6(7)
C8 C9 N1 C13 . . 176.8(5)
C13 C12 C11 C10 . . -2.7(10)
C9 C10 C11 C12 . . 0.6(8)
C9 N1 C13 C12 . . -0.5(10)
C11 C12 C13 N1 . . 2.8(13)
