#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/50/2235082.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_2235082
loop_
_publ_author_name
'Zhao, Jing'
'Zhang, Heng'
'Zhai, Xueliang'
'Zhu, Guoyi'
_publ_section_title
;
 Bis(2-aminomethyl-1H-benzimidazole-κ²N²,N³)bis(nitrato-κO)copper(II)
;
_journal_coeditor_code           HY2548
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m767
_journal_paper_doi               10.1107/S1600536812020910
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Cu (N O3)2 (C8 H9 N3)2]'
_chemical_formula_moiety         'C16 H18 Cu N8 O6'
_chemical_formula_sum            'C16 H18 Cu N8 O6'
_chemical_formula_weight         481.93
_chemical_name_systematic
;
Bis(2-aminomethyl-1H-benzimidazole-
κ²N²,N³)bis(nitrato-κO)copper(II)
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                120.00
_cell_formula_units_Z            9
_cell_length_a                   24.6913(8)
_cell_length_b                   24.6913(8)
_cell_length_c                   7.9620(5)
_cell_measurement_reflns_used    5478
_cell_measurement_temperature    184(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.73
_cell_volume                     4203.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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      184(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0109
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7196
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    1.226
_exptl_absorpt_correction_T_max  0.8769
_exptl_absorpt_correction_T_min  0.6806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2223
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0233
_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)+(0.0358P)²+6.4022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0634
_reflns_number_gt                1764
_reflns_number_total             1833
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2548.cif
_cod_data_source_block           I
_cod_original_cell_volume        4203.8(4)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2235082
_cod_database_fobs_code          2235082
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.8333 0.1667 0.1667 0.01942(10) Uani d S 1 2
O O1 0.85026(6) 0.28108(7) 0.46236(18) 0.0427(3) Uani d . 1 1
O O2 0.89291(6) 0.22280(5) 0.43740(16) 0.0339(3) Uani d . 1 1
O O3 0.94763(5) 0.31844(5) 0.52565(15) 0.0321(3) Uani d . 1 1
N N1 0.84262(6) 0.24335(6) 0.05919(15) 0.0205(3) Uani d . 1 1
N N2 0.89615(6) 0.31981(6) -0.12266(16) 0.0241(3) Uani d . 1 1
H H2 0.9235 0.3420 -0.2009 0.029 Uiso calc R 1 1
N N3 0.90693(6) 0.18332(6) 0.01943(15) 0.0222(3) Uani d . 1 1
H H3A 0.9417 0.1958 0.0856 0.027 Uiso calc R 1 1
H H3B 0.8986 0.1469 -0.0339 0.027 Uiso calc R 1 1
N N4 0.89671(6) 0.27418(6) 0.47583(16) 0.0249(3) Uani d . 1 1
C C1 0.92024(7) 0.23207(7) -0.10792(19) 0.0237(3) Uani d . 1 1
H H1A 0.9053 0.2126 -0.2196 0.028 Uiso calc R 1 1
H H1B 0.9658 0.2615 -0.1149 0.028 Uiso calc R 1 1
C C2 0.88719(7) 0.26609(7) -0.05640(18) 0.0207(3) Uani d . 1 1
C C3 0.82031(7) 0.28550(7) 0.06771(18) 0.0212(3) Uani d . 1 1
C C4 0.77224(8) 0.28515(8) 0.1601(2) 0.0283(3) Uani d . 1 1
H H4 0.7479 0.2524 0.2367 0.034 Uiso calc R 1 1
C C5 0.76134(8) 0.33433(8) 0.1360(2) 0.0326(4) Uani d . 1 1
H H5 0.7284 0.3348 0.1967 0.039 Uiso calc R 1 1
C C6 0.79714(9) 0.38357(8) 0.0253(2) 0.0349(4) Uani d . 1 1
H H6 0.7886 0.4169 0.0140 0.042 Uiso calc R 1 1
C C7 0.84461(8) 0.38431(8) -0.0675(2) 0.0319(4) Uani d . 1 1
H H7 0.8693 0.4176 -0.1426 0.038 Uiso calc R 1 1
C C8 0.85467(7) 0.33414(7) -0.04615(18) 0.0232(3) Uani d . 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'
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
N1 Cu1 N1 . 13_655 179.9990(10)
N1 Cu1 N3 . . 83.84(5)
N1 Cu1 N3 13_655 . 96.16(5)
N1 Cu1 N3 . 13_655 96.16(5)
N1 Cu1 N3 13_655 13_655 83.84(5)
N3 Cu1 N3 . 13_655 180.00(5)
N1 Cu1 O2 . . 94.86(4)
N1 Cu1 O2 13_655 . 85.14(4)
N3 Cu1 O2 . . 99.29(5)
N3 Cu1 O2 13_655 . 80.71(5)
N4 O2 Cu1 . . 118.50(9)
C2 N1 C3 . . 105.70(12)
C2 N1 Cu1 . . 112.29(10)
C3 N1 Cu1 . . 141.90(10)
C2 N2 C8 . . 107.67(12)
C2 N2 H2 . . 126.2
C8 N2 H2 . . 126.2
C1 N3 Cu1 . . 111.94(9)
C1 N3 H3A . . 109.2
Cu1 N3 H3A . . 109.2
C1 N3 H3B . . 109.2
Cu1 N3 H3B . . 109.2
H3A N3 H3B . . 107.9
O1 N4 O3 . . 120.07(13)
O1 N4 O2 . . 120.38(14)
O3 N4 O2 . . 119.55(13)
N3 C1 C2 . . 107.95(12)
N3 C1 H1A . . 110.1
C2 C1 H1A . . 110.1
N3 C1 H1B . . 110.1
C2 C1 H1B . . 110.1
H1A C1 H1B . . 108.4
N1 C2 N2 . . 112.60(13)
N1 C2 C1 . . 121.64(13)
N2 C2 C1 . . 125.70(13)
C4 C3 N1 . . 132.16(14)
C4 C3 C8 . . 119.72(14)
N1 C3 C8 . . 108.09(13)
C5 C4 C3 . . 117.45(15)
C5 C4 H4 . . 121.3
C3 C4 H4 . . 121.3
C4 C5 C6 . . 122.28(16)
C4 C5 H5 . . 118.9
C6 C5 H5 . . 118.9
C7 C6 C5 . . 120.84(15)
C7 C6 H6 . . 119.6
C5 C6 H6 . . 119.6
C6 C7 C8 . . 116.89(15)
C6 C7 H7 . . 121.6
C8 C7 H7 . . 121.6
N2 C8 C7 . . 131.30(15)
N2 C8 C3 . . 105.93(13)
C7 C8 C3 . . 122.77(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu1 N1 1.9839(12)
Cu1 N3 2.0244(12)
Cu1 O2 2.5870(12)
O1 N4 1.2454(18)
O2 N4 1.2621(17)
O3 N4 1.2483(17)
N1 C2 1.3250(19)
N1 C3 1.4016(19)
N2 C2 1.3390(19)
N2 C8 1.381(2)
N2 H2 0.8800
N3 C1 1.4798(19)
N3 H3A 0.9200
N3 H3B 0.9200
C1 C2 1.492(2)
C1 H1A 0.9900
C1 H1B 0.9900
C3 C4 1.393(2)
C3 C8 1.402(2)
C4 C5 1.382(2)
C4 H4 0.9500
C5 C6 1.401(3)
C5 H5 0.9500
C6 C7 1.378(3)
C6 H6 0.9500
C7 C8 1.390(2)
C7 H7 0.9500
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
N3 H3A O1 8_644 0.92 2.42 3.266(2) 153
N3 H3A O3 8_644 0.92 2.37 3.0521(17) 131
N3 H3B O1 13_655 0.92 2.33 3.1036(19) 142
N2 H2 O3 6_664 0.88 2.50 3.0276(18) 119
N2 H2 O3 1_554 0.88 2.40 3.0823(18) 134
N2 H2 O2 6_664 0.88 2.20 2.8901(17) 135
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139083831
