#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/85/2218511.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_2218511
loop_
_publ_author_name
'Song, Wen-Dong'
'Huang, Xiang-Hu'
'Wang, Hui'
_publ_section_title
Bis(1H-benzimidazole-κN³)bis(4-methylbenzoato-κ²O,O')copper(II)
_journal_coeditor_code           RZ2208
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m764
_journal_paper_doi               10.1107/S1600536808012440
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu (C8 H7 O2)2 (C7 H6 N2)2]'
_chemical_formula_moiety         'C30 H26 Cu N4 O4'
_chemical_formula_sum            'C30 H26 Cu N4 O4'
_chemical_formula_weight         570.10
_chemical_name_systematic
;
Bis(1H-benzimidazole-\kN³)bis(4-methylbenzoato-
κ²O,O')copper(II)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.687(2)
_cell_angle_beta                 96.3900(10)
_cell_angle_gamma                104.776(3)
_cell_formula_units_Z            1
_cell_length_a                   7.2623(2)
_cell_length_b                   7.60680(10)
_cell_length_c                   12.9624(2)
_cell_measurement_reflns_used    3600
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      1.36
_cell_volume                     673.53(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_diffrn_measurement_method       'φ and 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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8200
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  0.8478
_exptl_absorpt_correction_T_min  0.7264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             295
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1115P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                2445
_reflns_number_total             2743
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2208.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        673.54(3)
_cod_database_code               2218511
_cod_database_fobs_code          2218511
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C C1 0.3775(3) 0.6448(3) 0.56672(17) 0.0404(5) Uani d . 1
H H1 0.4583 0.6988 0.6312 0.048 Uiso calc R 1
C C2 0.1775(3) 0.4328(3) 0.43989(18) 0.0397(5) Uani d . 1
C C3 0.0533(4) 0.2729(3) 0.3739(2) 0.0516(6) Uani d . 1
H H3 0.0277 0.1586 0.3942 0.062 Uiso calc R 1
C C4 -0.0289(4) 0.2922(4) 0.2778(2) 0.0602(7) Uani d . 1
H H4 -0.1113 0.1882 0.2313 0.072 Uiso calc R 1
C C5 0.0079(4) 0.4657(4) 0.2474(2) 0.0553(7) Uani d . 1
H H5 -0.0517 0.4739 0.1818 0.066 Uiso calc R 1
C C6 0.1304(3) 0.6235(3) 0.31304(18) 0.0449(5) Uani d . 1
H H6 0.1530 0.7380 0.2931 0.054 Uiso calc R 1
C C7 0.2189(3) 0.6062(3) 0.40969(17) 0.0355(4) Uani d . 1
C C15 0.5949(3) 0.8828(3) 0.31242(16) 0.0400(5) Uani d . 1
C C16 0.5876(4) 0.8343(3) 0.19460(17) 0.0404(5) Uani d . 1
C C17 0.4260(4) 0.8288(3) 0.12438(18) 0.0462(5) Uani d . 1
H H17 0.3205 0.8574 0.1503 0.055 Uiso calc R 1
C C18 0.4215(4) 0.7808(4) 0.01597(18) 0.0553(7) Uani d . 1
H H18 0.3117 0.7766 -0.0299 0.066 Uiso calc R 1
C C19 0.5742(5) 0.7394(3) -0.02547(19) 0.0548(7) Uani d . 1
C C20 0.7351(5) 0.7454(4) 0.0439(2) 0.0631(8) Uani d . 1
H H20 0.8405 0.7179 0.0172 0.076 Uiso calc R 1
C C21 0.7426(4) 0.7920(4) 0.1535(2) 0.0547(6) Uani d . 1
H H21 0.8522 0.7947 0.1990 0.066 Uiso calc R 1
C C22 0.5672(6) 0.6885(4) -0.1443(2) 0.0736(9) Uani d . 1
H H22A 0.4408 0.6111 -0.1768 0.110 Uiso calc R 1
H H22B 0.6610 0.6226 -0.1589 0.110 Uiso calc R 1
H H22C 0.5955 0.7996 -0.1725 0.110 Uiso calc R 1
Cu Cu1 0.5000 1.0000 0.5000 0.03466(16) Uani d S 1
N N1 0.3479(3) 0.7375(2) 0.49250(13) 0.0363(4) Uani d . 1
N N2 0.2793(3) 0.4642(3) 0.54000(15) 0.0423(4) Uani d . 1
H H2 0.2800 0.3829 0.5787 0.051 Uiso calc R 1
O O1 0.4718(2) 0.9625(2) 0.34485(11) 0.0403(4) Uani d . 1
O O2 0.7185(3) 0.8455(2) 0.37312(13) 0.0503(4) Uani d . 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'
Cu Cu 0.3201 1.2651 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 N2 . . 113.20(19)
N1 C1 H1 . . 123.4
N2 C1 H1 . . 123.4
N2 C2 C3 . . 132.2(2)
N2 C2 C7 . . 105.66(19)
C3 C2 C7 . . 122.2(2)
C4 C3 C2 . . 116.8(2)
C4 C3 H3 . . 121.6
C2 C3 H3 . . 121.6
C3 C4 C5 . . 121.7(2)
C3 C4 H4 . . 119.2
C5 C4 H4 . . 119.2
C6 C5 C4 . . 121.3(2)
C6 C5 H5 . . 119.3
C4 C5 H5 . . 119.3
C5 C6 C7 . . 117.9(2)
C5 C6 H6 . . 121.0
C7 C6 H6 . . 121.0
C6 C7 N1 . . 131.56(19)
C6 C7 C2 . . 120.1(2)
N1 C7 C2 . . 108.32(19)
O2 C15 O1 . . 123.3(2)
O2 C15 C16 . . 119.9(2)
O1 C15 C16 . . 116.81(19)
C21 C16 C17 . . 118.4(2)
C21 C16 C15 . . 120.2(2)
C17 C16 C15 . . 121.3(2)
C18 C17 C16 . . 120.3(2)
C18 C17 H17 . . 119.9
C16 C17 H17 . . 119.9
C19 C18 C17 . . 121.8(3)
C19 C18 H18 . . 119.1
C17 C18 H18 . . 119.1
C18 C19 C20 . . 118.2(2)
C18 C19 C22 . . 121.0(3)
C20 C19 C22 . . 120.8(3)
C19 C20 C21 . . 121.2(3)
C19 C20 H20 . . 119.4
C21 C20 H20 . . 119.4
C16 C21 C20 . . 120.2(3)
C16 C21 H21 . . 119.9
C20 C21 H21 . . 119.9
C19 C22 H22A . . 109.5
C19 C22 H22B . . 109.5
H22A C22 H22B . . 109.5
C19 C22 H22C . . 109.5
H22A C22 H22C . . 109.5
H22B C22 H22C . . 109.5
O1 Cu1 O1 2_676 . 180.00(10)
O1 Cu1 N1 2_676 . 88.20(6)
O1 Cu1 N1 . . 91.80(6)
O1 Cu1 N1 2_676 2_676 91.80(6)
O1 Cu1 N1 . 2_676 88.20(6)
N1 Cu1 N1 . 2_676 180.00(11)
C1 N1 C7 . . 105.17(17)
C1 N1 Cu1 . . 122.68(15)
C7 N1 Cu1 . . 131.45(14)
C1 N2 C2 . . 107.64(18)
C1 N2 H2 . . 126.2
C2 N2 H2 . . 126.2
C15 O1 Cu1 . . 109.52(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.315(3)
C1 N2 . 1.342(3)
C1 H1 . 0.9300
C2 N2 . 1.371(3)
C2 C3 . 1.394(3)
C2 C7 . 1.407(3)
C3 C4 . 1.368(4)
C3 H3 . 0.9300
C4 C5 . 1.410(4)
C4 H4 . 0.9300
C5 C6 . 1.378(3)
C5 H5 . 0.9300
C6 C7 . 1.386(3)
C6 H6 . 0.9300
C7 N1 . 1.402(3)
C15 O2 . 1.246(3)
C15 O1 . 1.272(3)
C15 C16 . 1.501(3)
C16 C21 . 1.384(4)
C16 C17 . 1.390(3)
C17 C18 . 1.386(3)
C17 H17 . 0.9300
C18 C19 . 1.368(4)
C18 H18 . 0.9300
C19 C20 . 1.379(4)
C19 C22 . 1.516(3)
C20 C21 . 1.396(4)
C20 H20 . 0.9300
C21 H21 . 0.9300
C22 H22A . 0.9600
C22 H22B . 0.9600
C22 H22C . 0.9600
Cu1 O1 2_676 1.9630(14)
Cu1 O1 . 1.9630(14)
Cu1 N1 . 2.0007(16)
Cu1 N1 2_676 2.0007(16)
N2 H2 . 0.8600
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
N2 H2 O2 2_666 0.86 1.95 2.780(2) 163.4
