#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/70/2217082.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_2217082
loop_
_publ_author_name
'Ruiting Xue'
'Meiju Niu'
'Jianmin Dou'
'Daqi Wang'
_publ_section_title
;
 Bis[2-(2-hydroxy-3-methoxyphenyl)benzimidazolium]
 tetrachloridocuprate(II) methanol disolvate
;
_journal_coeditor_code           HB2652
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m211
_journal_page_last               m211
_journal_paper_doi               10.1107/S1600536807066214
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '(C14 H13 N2 O2)2 [Cu Cl4] , 2C H4 O'
_chemical_formula_moiety         '2C14 H13 N2 O2 + , Cu Cl4 2- , 2C H4 O'
_chemical_formula_sum            'C30 H34 Cl4 Cu N4 O6'
_chemical_formula_weight         751.95
_chemical_name_systematic
;
Bis[2-(2-hydroxy-3-methoxyphenyl)benzimidazolium] tetrachloridocuprate(II)
methanol disolvate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.406(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.992(2)
_cell_length_b                   9.9694(16)
_cell_length_c                   19.849(3)
_cell_measurement_reflns_used    3347
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.520
_cell_measurement_theta_min      2.370
_cell_volume                     3358.0(8)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8468
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.016
_exptl_absorpt_correction_T_max  0.757
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1548
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0348
_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)+(0.0475P)²+3.5756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2273
_reflns_number_total             2968
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2652.cif
_cod_data_source_block           I
_cod_original_cell_volume        3358.1(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2217082
_cod_database_fobs_code          2217082
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Cl Cl1 0.43726(4) 1.01765(8) 0.16383(4) 0.0528(2) Uani d . 1
Cu Cu1 0.5000 0.87387(5) 0.2500 0.03965(16) Uani d S 1
Cl Cl2 0.40516(4) 0.72185(8) 0.24813(5) 0.0618(2) Uani d . 1
N N1 0.77757(12) 0.5015(2) 0.52156(11) 0.0393(5) Uani d . 1
H H1 0.8090 0.5266 0.5626 0.047 Uiso calc R 1
N N2 0.67538(14) 0.4895(3) 0.42615(12) 0.0476(6) Uani d . 1
H H2 0.6298 0.5056 0.3953 0.057 Uiso calc R 1
O O1 0.76890(12) 0.6556(2) 0.62645(10) 0.0606(6) Uani d . 1
H H1A 0.7874 0.7034 0.6617 0.091 Uiso calc R 1
O O2 0.70083(13) 0.8504(2) 0.67617(11) 0.0651(6) Uani d . 1
O O3 0.52158(14) 0.4866(3) 0.33663(14) 0.0859(9) Uani d . 1
H H3 0.4981 0.5543 0.3174 0.129 Uiso calc R 1
C C1 0.66881(15) 0.6608(3) 0.51403(14) 0.0414(7) Uani d . 1
C C2 0.70078(15) 0.7102(3) 0.58301(15) 0.0425(7) Uani d . 1
C C3 0.66309(17) 0.8123(3) 0.60765(16) 0.0463(7) Uani d . 1
C C4 0.59298(18) 0.8638(3) 0.56282(18) 0.0533(8) Uani d . 1
H H4 0.5665 0.9296 0.5792 0.064 Uiso calc R 1
C C5 0.56225(17) 0.8174(4) 0.49376(18) 0.0585(9) Uani d . 1
H H5 0.5159 0.8549 0.4633 0.070 Uiso calc R 1
C C6 0.59831(17) 0.7175(3) 0.46896(16) 0.0524(8) Uani d . 1
H H6 0.5762 0.6870 0.4223 0.063 Uiso calc R 1
C C7 0.6671(2) 0.9575(4) 0.7043(2) 0.0764(11) Uani d . 1
H H7A 0.6583 1.0334 0.6729 0.115 Uiso calc R 1
H H7B 0.7024 0.9823 0.7506 0.115 Uiso calc R 1
H H7C 0.6178 0.9287 0.7084 0.115 Uiso calc R 1
C C8 0.70637(15) 0.5539(3) 0.48807(14) 0.0401(6) Uani d . 1
C C9 0.72747(17) 0.3928(3) 0.41891(15) 0.0459(7) Uani d . 1
C C10 0.79306(16) 0.4004(3) 0.48014(14) 0.0410(7) Uani d . 1
C C11 0.85731(17) 0.3171(3) 0.49069(16) 0.0489(7) Uani d . 1
H H11 0.9014 0.3226 0.5317 0.059 Uiso calc R 1
C C12 0.85291(19) 0.2254(3) 0.43757(18) 0.0586(8) Uani d . 1
H H12 0.8948 0.1671 0.4428 0.070 Uiso calc R 1
C C13 0.7865(2) 0.2184(4) 0.37584(19) 0.0683(10) Uani d . 1
H H13 0.7858 0.1563 0.3407 0.082 Uiso calc R 1
C C14 0.7228(2) 0.2999(4) 0.36564(17) 0.0635(9) Uani d . 1
H H14 0.6785 0.2935 0.3250 0.076 Uiso calc R 1
C C15 0.4684(3) 0.3940(5) 0.3439(3) 0.121(2) Uani d . 1
H H15A 0.4913 0.3447 0.3875 0.182 Uiso calc R 1
H H15B 0.4547 0.3333 0.3041 0.182 Uiso calc R 1
H H15C 0.4218 0.4393 0.3453 0.182 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 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'
Cu Cu 0.3201 1.2651 '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'
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
Cl1 Cu1 Cl1 2_655 . 99.99(5) y
Cl1 Cu1 Cl2 2_655 . 128.83(3) y
Cl1 Cu1 Cl2 . . 103.30(3) y
Cl1 Cu1 Cl2 2_655 2_655 103.30(3) ?
Cl1 Cu1 Cl2 . 2_655 128.83(3) ?
Cl2 Cu1 Cl2 . 2_655 96.38(5) y
C8 N1 C10 . . 109.7(2) ?
C8 N1 H1 . . 125.1 ?
C10 N1 H1 . . 125.1 ?
C8 N2 C9 . . 109.9(2) ?
C8 N2 H2 . . 125.0 ?
C9 N2 H2 . . 125.0 ?
C2 O1 H1A . . 109.5 ?
C3 O2 C7 . . 117.7(2) ?
C15 O3 H3 . . 109.5 ?
C2 C1 C6 . . 118.4(3) ?
C2 C1 C8 . . 121.6(2) ?
C6 C1 C8 . . 120.0(3) ?
O1 C2 C1 . . 118.4(2) ?
O1 C2 C3 . . 120.7(3) ?
C1 C2 C3 . . 120.9(2) ?
O2 C3 C4 . . 126.1(3) ?
O2 C3 C2 . . 114.5(2) ?
C4 C3 C2 . . 119.4(3) ?
C5 C4 C3 . . 119.8(3) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C6 C5 C4 . . 121.5(3) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C1 . . 120.0(3) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
O2 C7 H7A . . 109.5 ?
O2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N2 C8 N1 . . 107.9(2) ?
N2 C8 C1 . . 125.6(2) ?
N1 C8 C1 . . 126.5(2) ?
N2 C9 C10 . . 106.2(3) ?
N2 C9 C14 . . 132.3(3) ?
C10 C9 C14 . . 121.5(3) ?
C11 C10 N1 . . 132.1(3) ?
C11 C10 C9 . . 121.7(3) ?
N1 C10 C9 . . 106.2(2) ?
C12 C11 C10 . . 116.8(3) ?
C12 C11 H11 . . 121.6 ?
C10 C11 H11 . . 121.6 ?
C11 C12 C13 . . 121.2(3) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
C14 C13 C12 . . 122.1(3) ?
C14 C13 H13 . . 119.0 ?
C12 C13 H13 . . 119.0 ?
C13 C14 C9 . . 116.7(3) ?
C13 C14 H14 . . 121.6 ?
C9 C14 H14 . . 121.6 ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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
Cl1 Cu1 . 2.2297(8) y
Cu1 Cl1 2_655 2.2297(8) ?
Cu1 Cl2 . 2.2732(8) y
Cu1 Cl2 2_655 2.2732(8) ?
N1 C8 . 1.338(3) ?
N1 C10 . 1.386(3) ?
N1 H1 . 0.8600 ?
N2 C8 . 1.334(4) ?
N2 C9 . 1.385(4) ?
N2 H2 . 0.8600 ?
O1 C2 . 1.356(3) ?
O1 H1A . 0.8200 ?
O2 C3 . 1.357(4) ?
O2 C7 . 1.431(4) ?
O3 C15 . 1.372(5) ?
O3 H3 . 0.8200 ?
C1 C2 . 1.387(4) ?
C1 C6 . 1.405(4) ?
C1 C8 . 1.445(4) ?
C2 C3 . 1.398(4) ?
C3 C4 . 1.378(4) ?
C4 C5 . 1.377(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.366(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C9 C10 . 1.386(4) ?
C9 C14 . 1.388(4) ?
C10 C11 . 1.382(4) ?
C11 C12 . 1.377(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.400(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.364(5) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
N1 H1 O1 . 0.86 2.09 2.634(3) 120
N2 H2 O3 . 0.86 1.92 2.747(3) 162
O3 H3 Cl2 . 0.82 2.44 3.245(3) 168
N1 H1 Cl1 8_566 0.86 2.55 3.298(2) 147
O1 H1A Cl2 8_566 0.82 2.36 3.066(2) 145
