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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/42/4504233.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_4504233
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            'C24 H22 N8 O8 Zn'
_chemical_formula_weight         615.87
_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                97.17
_cell_angle_beta                 105.17
_cell_angle_gamma                90.86
_cell_formula_units_Z            1
_cell_length_a                   7.426
_cell_length_b                   8.957
_cell_length_c                   9.773
_cell_measurement_temperature    293(2)
_cell_volume                     621.718
_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_measurement_method       '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  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5298
_diffrn_reflns_theta_full        27.05
_diffrn_reflns_theta_max         27.05
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    1.056
_exptl_absorpt_correction_T_max  0.8927
_exptl_absorpt_correction_T_min  0.6256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 1997)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0272
_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)+(0.0506P)²+0.1451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                2471
_reflns_number_total             2670
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg070080j-file003.cif
_cod_data_source_block           9
_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        621.7
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4504233
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
Zn1 Zn 0.0000 1.0000 -0.5000 0.03098(10) Uani 1 2 d S
O3 O 0.25475(18) 0.93736(14) -0.56151(13) 0.0403(3) Uani 1 1 d .
O4 O 0.20010(18) 1.15803(15) -0.35724(14) 0.0398(3) Uani 1 1 d .
H4A H 0.3019 1.1477 -0.3743 0.060 Uiso 1 1 calc R
N4 N 0.2655(2) 0.84177(15) -0.66345(14) 0.0321(3) Uani 1 1 d .
O2 O 0.1232(2) 0.79839(18) -0.75992(16) 0.0556(4) Uani 1 1 d .
N1 N 0.0623(2) 0.83814(15) -0.35795(15) 0.0324(3) Uani 1 1 d .
O1 O 0.41670(19) 0.79048(17) -0.66878(17) 0.0553(4) Uani 1 1 d .
N3 N 0.2595(2) 0.37321(15) -0.10867(14) 0.0318(3) Uani 1 1 d .
C12 C 0.3114(2) 0.31134(18) 0.01838(18) 0.0323(3) Uani 1 1 d .
N2 N 0.2484(2) 0.54669(16) 0.07319(15) 0.0361(3) Uani 1 1 d .
H2A H 0.2314 0.6318 0.1183 0.043 Uiso 1 1 calc R
C7 C 0.3048(2) 0.41878(19) 0.13252(18) 0.0342(3) Uani 1 1 d .
C6 C 0.2245(2) 0.51397(17) -0.06988(17) 0.0297(3) Uani 1 1 d .
C3 C 0.1665(2) 0.62581(17) -0.16807(17) 0.0297(3) Uani 1 1 d .
C8 C 0.3502(3) 0.3879(2) 0.2742(2) 0.0459(4) Uani 1 1 d .
H8A H 0.3460 0.4606 0.3499 0.055 Uiso 1 1 calc R
C5 C 0.1055(3) 0.69866(19) -0.40206(18) 0.0367(4) Uani 1 1 d .
H5A H 0.0992 0.6732 -0.4985 0.044 Uiso 1 1 calc R
C1 C 0.0686(3) 0.87086(19) -0.21941(18) 0.0356(4) Uani 1 1 d .
H1A H 0.0373 0.9665 -0.1868 0.043 Uiso 1 1 calc R
C11 C 0.3644(3) 0.1655(2) 0.0426(2) 0.0438(4) Uani 1 1 d .
H11A H 0.3694 0.0921 -0.0323 0.053 Uiso 1 1 calc R
C4 C 0.1585(3) 0.59113(18) -0.31220(18) 0.0356(4) Uani 1 1 d .
H4B H 0.1886 0.4962 -0.3476 0.043 Uiso 1 1 calc R
C10 C 0.4085(3) 0.1353(2) 0.1815(2) 0.0494(5) Uani 1 1 d .
H10A H 0.4444 0.0393 0.2004 0.059 Uiso 1 1 calc R
C2 C 0.1192(3) 0.76916(19) -0.12263(17) 0.0356(4) Uani 1 1 d .
H2B H 0.1216 0.7967 -0.0272 0.043 Uiso 1 1 calc R
C9 C 0.4014(3) 0.2434(2) 0.2947(2) 0.0500(5) Uani 1 1 d .
H9A H 0.4321 0.2175 0.3870 0.060 Uiso 1 1 calc R
H4C H 0.203(3) 1.213(3) -0.290(3) 0.047(6) Uiso 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'
Zn Zn 0.2839 1.4301 '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
N1 Zn1 N1 180.0 2_574 .
N1 Zn1 O4 91.36(5) 2_574 2_574
N1 Zn1 O4 88.64(5) . 2_574
N1 Zn1 O4 88.64(5) 2_574 .
N1 Zn1 O4 91.36(5) . .
O4 Zn1 O4 180.00(7) 2_574 .
N1 Zn1 O3 86.59(5) 2_574 2_574
N1 Zn1 O3 93.41(5) . 2_574
O4 Zn1 O3 78.87(5) 2_574 2_574
O4 Zn1 O3 101.13(5) . 2_574
N1 Zn1 O3 93.41(5) 2_574 .
N1 Zn1 O3 86.59(5) . .
O4 Zn1 O3 101.13(5) 2_574 .
O4 Zn1 O3 78.87(5) . .
O3 Zn1 O3 180.0 2_574 .
N4 O3 Zn1 126.44(11) . .
Zn1 O4 H4A 109.5 . .
Zn1 O4 H4C 135.9(18) . .
H4A O4 H4C 114.1 . .
O1 N4 O2 119.67(14) . .
O1 N4 O3 120.49(14) . .
O2 N4 O3 119.84(14) . .
C1 N1 C5 117.08(14) . .
C1 N1 Zn1 121.92(11) . .
C5 N1 Zn1 120.94(11) . .
C6 N3 C12 104.56(13) . .
N3 C12 C7 109.94(14) . .
N3 C12 C11 129.95(16) . .
C7 C12 C11 120.10(16) . .
C6 N2 C7 107.20(13) . .
C6 N2 H2A 126.4 . .
C7 N2 H2A 126.4 . .
N2 C7 C12 105.46(14) . .
N2 C7 C8 131.99(17) . .
C12 C7 C8 122.55(16) . .
N3 C6 N2 112.83(14) . .
N3 C6 C3 124.82(14) . .
N2 C6 C3 122.35(14) . .
C2 C3 C4 117.30(14) . .
C2 C3 C6 122.29(14) . .
C4 C3 C6 120.40(14) . .
C9 C8 C7 116.05(19) . .
C9 C8 H8A 122.0 . .
C7 C8 H8A 122.0 . .
N1 C5 C4 123.49(15) . .
N1 C5 H5A 118.3 . .
C4 C5 H5A 118.3 . .
N1 C1 C2 122.97(15) . .
N1 C1 H1A 118.5 . .
C2 C1 H1A 118.5 . .
C10 C11 C12 117.28(18) . .
C10 C11 H11A 121.4 . .
C12 C11 H11A 121.4 . .
C5 C4 C3 119.32(15) . .
C5 C4 H4B 120.3 . .
C3 C4 H4B 120.3 . .
C11 C10 C9 122.17(17) . .
C11 C10 H10A 118.9 . .
C9 C10 H10A 118.9 . .
C1 C2 C3 119.82(15) . .
C1 C2 H2B 120.1 . .
C3 C2 H2B 120.1 . .
C8 C9 C10 121.85(18) . .
C8 C9 H9A 119.1 . .
C10 C9 H9A 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 2.1046(13) 2_574
Zn1 N1 2.1046(13) .
Zn1 O4 2.1254(12) 2_574
Zn1 O4 2.1254(12) .
Zn1 O3 2.1904(12) 2_574
Zn1 O3 2.1904(12) .
O3 N4 1.2500(17) .
O4 H4A 0.8200 .
O4 H4C 0.76(2) .
N4 O1 1.2309(19) .
N4 O2 1.2375(19) .
N1 C1 1.337(2) .
N1 C5 1.341(2) .
N3 C6 1.320(2) .
N3 C12 1.387(2) .
C12 C7 1.391(2) .
C12 C11 1.400(2) .
N2 C6 1.356(2) .
N2 C7 1.370(2) .
N2 H2A 0.8600 .
C7 C8 1.400(2) .
C6 C3 1.465(2) .
C3 C2 1.386(2) .
C3 C4 1.389(2) .
C8 C9 1.379(3) .
C8 H8A 0.9300 .
C5 C4 1.377(2) .
C5 H5A 0.9300 .
C1 C2 1.380(2) .
C1 H1A 0.9300 .
C11 C10 1.373(3) .
C11 H11A 0.9300 .
C4 H4B 0.9300 .
C10 C9 1.388(3) .
C10 H10A 0.9300 .
C2 H2B 0.9300 .
C9 H9A 0.9300 .
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
O4 H4A O1 0.82 2.07 2.8159(19) 150.5 2_674
N2 H2A O2 0.86 2.09 2.9233(19) 162.0 1_556
N2 H2A O1 0.86 2.44 3.096(2) 133.6 1_556
N2 H2A N4 0.86 2.62 3.4271(19) 157.3 1_556
O4 H4C N3 0.76(2) 2.09(2) 2.8380(18) 170(2) 1_565
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
N1 Zn1 O3 N4 -86.47(13) 2_574
N1 Zn1 O3 N4 93.53(13) .
O4 Zn1 O3 N4 5.59(14) 2_574
O4 Zn1 O3 N4 -174.41(14) .
O3 Zn1 O3 N4 -155(100) 2_574
Zn1 O3 N4 O1 -163.05(13) .
Zn1 O3 N4 O2 17.0(2) .
N1 Zn1 N1 C1 57(6) 2_574
O4 Zn1 N1 C1 -130.51(14) 2_574
O4 Zn1 N1 C1 49.49(14) .
O3 Zn1 N1 C1 -51.74(14) 2_574
O3 Zn1 N1 C1 128.26(14) .
N1 Zn1 N1 C5 -120(6) 2_574
O4 Zn1 N1 C5 52.34(13) 2_574
O4 Zn1 N1 C5 -127.66(13) .
O3 Zn1 N1 C5 131.11(13) 2_574
O3 Zn1 N1 C5 -48.89(13) .
C6 N3 C12 C7 0.38(18) .
C6 N3 C12 C11 -179.87(18) .
C6 N2 C7 C12 -0.31(18) .
C6 N2 C7 C8 179.63(19) .
N3 C12 C7 N2 -0.05(19) .
C11 C12 C7 N2 -179.82(16) .
N3 C12 C7 C8 -179.99(17) .
C11 C12 C7 C8 0.2(3) .
C12 N3 C6 N2 -0.60(19) .
C12 N3 C6 C3 179.17(15) .
C7 N2 C6 N3 0.6(2) .
C7 N2 C6 C3 -179.18(15) .
N3 C6 C3 C2 175.49(16) .
N2 C6 C3 C2 -4.8(3) .
N3 C6 C3 C4 -5.1(3) .
N2 C6 C3 C4 174.69(16) .
N2 C7 C8 C9 179.72(19) .
C12 C7 C8 C9 -0.3(3) .
C1 N1 C5 C4 -1.4(3) .
Zn1 N1 C5 C4 175.89(14) .
C5 N1 C1 C2 1.0(3) .
Zn1 N1 C1 C2 -176.29(14) .
N3 C12 C11 C10 -179.84(17) .
C7 C12 C11 C10 -0.1(3) .
N1 C5 C4 C3 0.8(3) .
C2 C3 C4 C5 0.2(3) .
C6 C3 C4 C5 -179.31(16) .
C12 C11 C10 C9 0.1(3) .
N1 C1 C2 C3 0.0(3) .
C4 C3 C2 C1 -0.6(3) .
C6 C3 C2 C1 178.91(16) .
C7 C8 C9 C10 0.4(3) .
C11 C10 C9 C8 -0.3(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168345050
