#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/71/2227162.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227162
loop_
_publ_author_name
'Wang, Jun'
'Dai, Chuntao'
'Zhao, Dongmei'
_publ_section_title
;
 Bis[2-(1H-benzimidazol-2-yl)benzoato]copper(II) dihydrate
;
_journal_coeditor_code           BG2369
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1306
_journal_page_last               m1307
_journal_paper_doi               10.1107/S1600536810037633
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu (C14 H9 N2 O2)2], 2H2 O'
_chemical_formula_moiety         'C28 H18 Cu N4 O4, 2(H2 O)'
_chemical_formula_sum            'C28 H22 Cu N4 O6'
_chemical_formula_weight         574.04
_chemical_name_systematic
;
Bis[2-(1H-benzimidazol-2-yl)benzoato]copper(II) dihydrate
;
_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                 115.7350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.6235(2)
_cell_length_b                   7.6920(2)
_cell_length_c                   16.1410(3)
_cell_measurement_reflns_used    4800
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      1.36
_cell_volume                     1299.99(5)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008b)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14480
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  0.8706
_exptl_absorpt_correction_T_min  0.8214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             590
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.333
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0457
_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)+(0.0379P)²+0.7646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                1854
_reflns_number_total             2974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bg2369.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227162
_cod_database_fobs_code          2227162
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_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.5000 0.5000 0.5000 0.03258(17) Uani d S 1 . .
C C1 0.5169(3) 0.8319(4) 0.6049(2) 0.0354(7) Uani d . 1 . .
C C2 0.4078(3) 0.9168(4) 0.5430(2) 0.0439(8) Uani d . 1 . .
H H2 0.3519 0.8648 0.4883 0.053 Uiso calc R 1 . .
C C3 0.3861(4) 1.0813(5) 0.5665(3) 0.0511(9) Uani d . 1 . .
H H3 0.3139 1.1414 0.5265 0.061 Uiso calc R 1 . .
C C4 0.4686(4) 1.1600(5) 0.6478(3) 0.0582(10) Uani d . 1 . .
H H4 0.4508 1.2721 0.6605 0.070 Uiso calc R 1 . .
C C5 0.5758(4) 1.0775(5) 0.7099(3) 0.0535(10) Uani d . 1 . .
H H5 0.6302 1.1301 0.7649 0.064 Uiso calc R 1 . .
C C6 0.5994(3) 0.9111(4) 0.6870(2) 0.0400(8) Uani d . 1 . .
C C7 0.6757(3) 0.6520(4) 0.6772(2) 0.0332(7) Uani d . 1 . .
C C8 0.7588(3) 0.4981(4) 0.7070(2) 0.0358(7) Uani d . 1 . .
C C9 0.8024(3) 0.4489(5) 0.7992(2) 0.0504(9) Uani d . 1 . .
H H9 0.7779 0.5126 0.8378 0.060 Uiso calc R 1 . .
C C10 0.8814(4) 0.3068(5) 0.8332(3) 0.0632(11) Uani d . 1 . .
H H10 0.9096 0.2750 0.8945 0.076 Uiso calc R 1 . .
C C11 0.9187(3) 0.2119(5) 0.7768(3) 0.0604(11) Uani d . 1 . .
H H11 0.9700 0.1141 0.7994 0.072 Uiso calc R 1 . .
C C12 0.8798(3) 0.2620(4) 0.6868(2) 0.0502(9) Uani d . 1 . .
H H12 0.9075 0.1995 0.6495 0.060 Uiso calc R 1 . .
C C13 0.7996(3) 0.4051(4) 0.6504(2) 0.0367(7) Uani d . 1 . .
C C14 0.7735(3) 0.4580(4) 0.5535(2) 0.0386(8) Uani d . 1 . .
N N1 0.5679(2) 0.6681(3) 0.60034(16) 0.0327(6) Uani d . 1 . .
N N2 0.6971(2) 0.7946(3) 0.73035(17) 0.0413(7) Uani d . 1 . .
H H2A 0.7614 0.8103 0.7828 0.050 Uiso calc R 1 . .
O O1 0.66231(18) 0.4956(3) 0.49508(13) 0.0392(5) Uani d . 1 . .
O O2 0.8661(2) 0.4584(4) 0.53508(16) 0.0636(8) Uani d . 1 . .
O O1W 0.8855(2) 0.8417(3) 0.90275(15) 0.0624(7) Uani d . 1 . .
H H1W 0.8680 0.8979 0.9406 0.094 Uiso d R 1 . .
H H2W 0.9618 0.8657 0.9144 0.094 Uiso d 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'
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
_geom_angle_publ_flag
O1 Cu1 O1 3_666 . 180.0 ?
O1 Cu1 N1 3_666 . 90.25(9) ?
O1 Cu1 N1 . . 89.75(9) ?
O1 Cu1 N1 3_666 3_666 89.75(9) ?
O1 Cu1 N1 . 3_666 90.25(9) ?
N1 Cu1 N1 . 3_666 180.0 ?
C2 C1 C6 . . 120.9(3) ?
C2 C1 N1 . . 131.1(3) ?
C6 C1 N1 . . 108.0(3) ?
C3 C2 C1 . . 117.0(3) ?
C3 C2 H2 . . 121.5 ?
C1 C2 H2 . . 121.5 ?
C2 C3 C4 . . 122.0(3) ?
C2 C3 H3 . . 119.0 ?
C4 C3 H3 . . 119.0 ?
C5 C4 C3 . . 121.8(3) ?
C5 C4 H4 . . 119.1 ?
C3 C4 H4 . . 119.1 ?
C4 C5 C6 . . 116.9(3) ?
C4 C5 H5 . . 121.5 ?
C6 C5 H5 . . 121.5 ?
N2 C6 C5 . . 132.7(3) ?
N2 C6 C1 . . 105.9(3) ?
C5 C6 C1 . . 121.4(3) ?
N1 C7 N2 . . 110.9(3) ?
N1 C7 C8 . . 126.7(3) ?
N2 C7 C8 . . 122.3(3) ?
C13 C8 C9 . . 119.2(3) ?
C13 C8 C7 . . 124.1(3) ?
C9 C8 C7 . . 116.6(3) ?
C10 C9 C8 . . 120.6(3) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C11 C10 C9 . . 120.2(3) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 119.8(3) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
C11 C12 C13 . . 121.3(3) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
C8 C13 C12 . . 118.9(3) ?
C8 C13 C14 . . 124.4(3) ?
C12 C13 C14 . . 116.4(3) ?
O2 C14 O1 . . 122.5(3) ?
O2 C14 C13 . . 116.4(3) ?
O1 C14 C13 . . 121.1(3) ?
C7 N1 C1 . . 106.4(2) ?
C7 N1 Cu1 . . 126.1(2) ?
C1 N1 Cu1 . . 127.5(2) ?
C7 N2 C6 . . 108.8(3) ?
C7 N2 H2A . . 125.6 ?
C6 N2 H2A . . 125.6 ?
C14 O1 Cu1 . . 132.8(2) ?
H1W O1W H2W . . 106.7 ?
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 3_666 1.9227(19) ?
Cu1 O1 . 1.9227(19) ?
Cu1 N1 . 1.951(2) ?
Cu1 N1 3_666 1.951(2) ?
C1 C2 . 1.390(4) ?
C1 C6 . 1.395(4) ?
C1 N1 . 1.407(4) ?
C2 C3 . 1.374(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.384(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.370(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.392(5) ?
C5 H5 . 0.9300 ?
C6 N2 . 1.376(4) ?
C7 N1 . 1.333(3) ?
C7 N2 . 1.347(3) ?
C7 C8 . 1.470(4) ?
C8 C13 . 1.396(4) ?
C8 C9 . 1.400(4) ?
C9 C10 . 1.379(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.376(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.376(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.396(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.513(4) ?
C14 O2 . 1.235(4) ?
C14 O1 . 1.259(3) ?
N2 H2A . 0.8600 ?
O1W H1W . 0.8415 ?
O1W H2W . 0.8432 ?
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 H2A O1W . 0.86 1.86 2.716(3) 172.6
O1W H1W O2 4_576 0.84 1.89 2.720(3) 167.4
O1W H2W O2 2_756 0.84 1.94 2.763(3) 165.4
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079469
