#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/42/4504234.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_4504234
loop_
_publ_author_name
'Li, Xiang-Ping'
'Pan, Mei'
'Zheng, Sheng-Run'
'Liu, Yong-Ru'
'He, Qi-Ting'
'Kang, Bei-Sheng'
'Su, Cheng-Yong'
_publ_section_title
;
 Dimension Increase via Hydrogen Bonding and Weak Coordination
 Interactions from Simple Complexes of 2-(Pyridyl)benzimidazole Ligands
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2481
_journal_paper_doi               10.1021/cg070080j
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C16 H15 Cu N3 O4'
_chemical_formula_weight         376.85
_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                103.06
_cell_angle_beta                 97.85
_cell_angle_gamma                104.11
_cell_formula_units_Z            2
_cell_length_a                   8.148
_cell_length_b                   9.688
_cell_length_c                   11.095
_cell_measurement_temperature    293(2)
_cell_volume                     810.214
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  SMART
_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  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6958
_diffrn_reflns_theta_full        27.08
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  0.8526
_exptl_absorpt_correction_T_min  0.5586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 1997)'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             386
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    geom
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0322
_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)+(0.0603P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                3046
_reflns_number_total             3495
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg070080j-file003.cif
_cod_data_source_block           10
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        810.2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4504234
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu -0.03934(3) 1.46057(3) -0.39861(2) 0.02835(11) Uani 1 1 d .
O4 O 0.2150(2) 1.5372(2) -0.32943(16) 0.0377(4) Uani 1 1 d .
O2 O -0.0055(2) 1.26931(19) -0.47539(17) 0.0416(4) Uani 1 1 d .
N1 N -0.1199(2) 1.4099(2) -0.23069(18) 0.0310(4) Uani 1 1 d .
N3 N -0.3096(3) 1.6123(2) 0.15211(18) 0.0354(4) Uani 1 1 d .
H3A H -0.3091 1.5441 0.1901 0.043 Uiso 1 1 calc R
C3 C -0.2358(3) 1.3546(3) -0.0177(2) 0.0378(5) Uani 1 1 d .
H3B H -0.2741 1.3355 0.0537 0.045 Uiso 1 1 calc R
C16 C 0.3203(3) 1.5888(2) -0.3935(2) 0.0304(5) Uani 1 1 d .
N2 N -0.2897(3) 1.7290(2) -0.0004(2) 0.0394(5) Uani 1 1 d .
C14 C 0.0348(3) 1.2450(3) -0.5817(2) 0.0332(5) Uani 1 1 d .
C5 C -0.1689(3) 1.5111(3) -0.1522(2) 0.0320(5) Uani 1 1 d .
H5A H -0.1626 1.6011 -0.1704 0.038 Uiso 1 1 calc R
C12 C -0.3300(3) 1.8163(3) 0.1023(2) 0.0398(5) Uani 1 1 d .
C4 C -0.2290(3) 1.4890(3) -0.0448(2) 0.0307(5) Uani 1 1 d .
C6 C -0.2766(3) 1.6101(3) 0.0344(2) 0.0316(5) Uani 1 1 d .
C1 C -0.1290(3) 1.2812(3) -0.2040(2) 0.0376(5) Uani 1 1 d .
H1B H -0.0965 1.2094 -0.2586 0.045 Uiso 1 1 calc R
C7 C -0.3436(3) 1.7437(3) 0.1981(2) 0.0380(5) Uani 1 1 d .
C15 C 0.5095(3) 1.6300(3) -0.3368(3) 0.0465(6) Uani 1 1 d .
H15A H 0.5756 1.6674 -0.3938 0.070 Uiso 1 1 calc R
H15B H 0.5392 1.5443 -0.3223 0.070 Uiso 1 1 calc R
H15C H 0.5348 1.7047 -0.2581 0.070 Uiso 1 1 calc R
C2 C -0.1847(4) 1.2502(3) -0.0988(3) 0.0430(6) Uani 1 1 d .
H2B H -0.1878 1.1596 -0.0825 0.052 Uiso 1 1 calc R
C11 C -0.3555(4) 1.9555(3) 0.1196(3) 0.0574(8) Uani 1 1 d .
H11A H -0.3460 2.0052 0.0572 0.069 Uiso 1 1 calc R
C13 C 0.0622(4) 1.0964(3) -0.6360(3) 0.0477(6) Uani 1 1 d .
H13A H 0.0423 1.0365 -0.5783 0.071 Uiso 1 1 calc R
H13B H 0.1787 1.1102 -0.6488 0.071 Uiso 1 1 calc R
H13C H -0.0170 1.0480 -0.7153 0.071 Uiso 1 1 calc R
C8 C -0.3859(4) 1.8070(4) 0.3116(3) 0.0568(8) Uani 1 1 d .
H8A H -0.3960 1.7588 0.3750 0.068 Uiso 1 1 calc R
C9 C -0.4118(5) 1.9444(4) 0.3246(4) 0.0716(10) Uani 1 1 d .
H9A H -0.4416 1.9896 0.3984 0.086 Uiso 1 1 calc R
C10 C -0.3951(5) 2.0172(4) 0.2316(4) 0.0706(10) Uani 1 1 d .
H10A H -0.4112 2.1109 0.2453 0.085 Uiso 1 1 calc R
O3 O 0.2782(2) 1.6053(2) -0.50019(16) 0.0386(4) Uani 1 1 d .
O1 O 0.0564(2) 1.33638(19) -0.64718(17) 0.0407(4) Uani 1 1 d .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 Cu1 O1 167.83(7) . 2_584
O2 Cu1 O3 90.15(8) . 2_584
O1 Cu1 O3 89.38(8) 2_584 2_584
O2 Cu1 O4 88.46(8) . .
O1 Cu1 O4 89.45(8) 2_584 .
O3 Cu1 O4 167.93(7) 2_584 .
O2 Cu1 N1 97.87(7) . .
O1 Cu1 N1 94.30(7) 2_584 .
O3 Cu1 N1 93.96(7) 2_584 .
O4 Cu1 N1 98.11(7) . .
O2 Cu1 Cu1 86.89(5) . 2_584
O1 Cu1 Cu1 80.98(5) 2_584 2_584
O3 Cu1 Cu1 83.17(5) 2_584 2_584
O4 Cu1 Cu1 84.77(5) . 2_584
N1 Cu1 Cu1 174.48(5) . 2_584
C16 O4 Cu1 121.89(14) . .
C14 O2 Cu1 120.30(15) . .
C1 N1 C5 117.9(2) . .
C1 N1 Cu1 123.70(16) . .
C5 N1 Cu1 118.32(15) . .
C6 N3 C7 106.9(2) . .
C6 N3 H3A 126.6 . .
C7 N3 H3A 126.6 . .
C2 C3 C4 118.7(2) . .
C2 C3 H3B 120.6 . .
C4 C3 H3B 120.6 . .
O3 C16 O4 124.8(2) . .
O3 C16 C15 117.9(2) . .
O4 C16 C15 117.3(2) . .
C6 N2 C12 104.6(2) . .
O2 C14 O1 124.8(2) . .
O2 C14 C13 118.3(2) . .
O1 C14 C13 116.9(2) . .
N1 C5 C4 123.5(2) . .
N1 C5 H5A 118.3 . .
C4 C5 H5A 118.3 . .
N2 C12 C11 129.9(3) . .
N2 C12 C7 109.9(2) . .
C11 C12 C7 120.2(3) . .
C5 C4 C3 117.8(2) . .
C5 C4 C6 118.0(2) . .
C3 C4 C6 124.3(2) . .
N2 C6 N3 113.2(2) . .
N2 C6 C4 123.2(2) . .
N3 C6 C4 123.6(2) . .
N1 C1 C2 122.7(2) . .
N1 C1 H1B 118.7 . .
C2 C1 H1B 118.7 . .
N3 C7 C8 133.0(3) . .
N3 C7 C12 105.5(2) . .
C8 C7 C12 121.5(3) . .
C16 C15 H15A 109.5 . .
C16 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C16 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C1 C2 C3 119.4(2) . .
C1 C2 H2B 120.3 . .
C3 C2 H2B 120.3 . .
C10 C11 C12 117.9(3) . .
C10 C11 H11A 121.1 . .
C12 C11 H11A 121.1 . .
C14 C13 H13A 109.5 . .
C14 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C14 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C9 C8 C7 116.5(3) . .
C9 C8 H8A 121.7 . .
C7 C8 H8A 121.7 . .
C8 C9 C10 122.0(3) . .
C8 C9 H9A 119.0 . .
C10 C9 H9A 119.0 . .
C11 C10 C9 121.9(3) . .
C11 C10 H10A 119.1 . .
C9 C10 H10A 119.1 . .
C16 O3 Cu1 125.18(15) . 2_584
C14 O1 Cu1 126.96(16) . 2_584
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.9584(17) .
Cu1 O1 1.9617(17) 2_584
Cu1 O3 1.9820(16) 2_584
Cu1 O4 1.9983(16) .
Cu1 N1 2.1755(19) .
Cu1 Cu1 2.6435(5) 2_584
O4 C16 1.268(3) .
O2 C14 1.254(3) .
N1 C1 1.333(3) .
N1 C5 1.334(3) .
N3 C6 1.365(3) .
N3 C7 1.369(3) .
N3 H3A 0.8600 .
C3 C2 1.379(4) .
C3 C4 1.391(3) .
C3 H3B 0.9300 .
C16 O3 1.243(3) .
C16 C15 1.501(3) .
N2 C6 1.317(3) .
N2 C12 1.387(3) .
C14 O1 1.262(3) .
C14 C13 1.513(3) .
C5 C4 1.389(3) .
C5 H5A 0.9300 .
C12 C11 1.389(4) .
C12 C7 1.403(4) .
C4 C6 1.466(3) .
C1 C2 1.376(3) .
C1 H1B 0.9300 .
C7 C8 1.398(4) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C2 H2B 0.9300 .
C11 C10 1.368(5) .
C11 H11A 0.9300 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C8 C9 1.378(5) .
C8 H8A 0.9300 .
C9 C10 1.379(6) .
C9 H9A 0.9300 .
C10 H10A 0.9300 .
O3 Cu1 1.9820(16) 2_584
O1 Cu1 1.9617(17) 2_584
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O4 0.86 2.03 2.825(3) 153.3 2_585
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O2 Cu1 O4 C16 85.63(18) . .
O1 Cu1 O4 C16 -82.38(18) 2_584 .
O3 Cu1 O4 C16 2.1(4) 2_584 .
N1 Cu1 O4 C16 -176.64(18) . .
Cu1 Cu1 O4 C16 -1.39(17) 2_584 .
O1 Cu1 O2 C14 -5.4(5) 2_584 .
O3 Cu1 O2 C14 82.37(19) 2_584 .
O4 Cu1 O2 C14 -85.64(19) . .
N1 Cu1 O2 C14 176.39(18) . .
Cu1 Cu1 O2 C14 -0.79(18) 2_584 .
O2 Cu1 N1 C1 1.9(2) . .
O1 Cu1 N1 C1 -177.73(19) 2_584 .
O3 Cu1 N1 C1 92.60(19) 2_584 .
O4 Cu1 N1 C1 -87.67(19) . .
Cu1 Cu1 N1 C1 151.2(5) 2_584 .
O2 Cu1 N1 C5 -175.55(16) . .
O1 Cu1 N1 C5 4.83(17) 2_584 .
O3 Cu1 N1 C5 -84.85(17) 2_584 .
O4 Cu1 N1 C5 94.89(17) . .
Cu1 Cu1 N1 C5 -26.3(7) 2_584 .
Cu1 O4 C16 O3 4.4(3) . .
Cu1 O4 C16 C15 -174.39(16) . .
Cu1 O2 C14 O1 -0.1(3) . .
Cu1 O2 C14 C13 179.07(16) . .
C1 N1 C5 C4 -0.1(3) . .
Cu1 N1 C5 C4 177.49(16) . .
C6 N2 C12 C11 178.6(3) . .
C6 N2 C12 C7 -1.1(3) . .
N1 C5 C4 C3 0.8(3) . .
N1 C5 C4 C6 179.2(2) . .
C2 C3 C4 C5 -0.6(3) . .
C2 C3 C4 C6 -178.9(2) . .
C12 N2 C6 N3 1.4(3) . .
C12 N2 C6 C4 -177.8(2) . .
C7 N3 C6 N2 -1.1(3) . .
C7 N3 C6 C4 178.0(2) . .
C5 C4 C6 N2 10.4(3) . .
C3 C4 C6 N2 -171.4(2) . .
C5 C4 C6 N3 -168.7(2) . .
C3 C4 C6 N3 9.6(4) . .
C5 N1 C1 C2 -0.8(4) . .
Cu1 N1 C1 C2 -178.25(19) . .
C6 N3 C7 C8 179.7(3) . .
C6 N3 C7 C12 0.4(3) . .
N2 C12 C7 N3 0.4(3) . .
C11 C12 C7 N3 -179.3(2) . .
N2 C12 C7 C8 -179.0(2) . .
C11 C12 C7 C8 1.3(4) . .
N1 C1 C2 C3 0.9(4) . .
C4 C3 C2 C1 -0.2(4) . .
N2 C12 C11 C10 179.8(3) . .
C7 C12 C11 C10 -0.5(4) . .
N3 C7 C8 C9 -179.9(3) . .
C12 C7 C8 C9 -0.6(4) . .
C7 C8 C9 C10 -0.8(5) . .
C12 C11 C10 C9 -0.8(6) . .
C8 C9 C10 C11 1.5(6) . .
O4 C16 O3 Cu1 -5.6(3) . 2_584
C15 C16 O3 Cu1 173.18(16) . 2_584
O2 C14 O1 Cu1 1.6(4) . 2_584
C13 C14 O1 Cu1 -177.62(16) . 2_584
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145465
