#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/26/4322601.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_4322601
loop_
_publ_author_name
'Craig J. Matthews'
'William Clegg'
'Sarah L. Heath'
'Nicola C. Martin'
'M. N. Stuart Hill'
'Joyce C. Lockhart'
_publ_section_title
;
 Coordination of Zn(II), Cd(II), Hg(II), and Ag(I) by Bis(benzimidazole)
 Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              199
_journal_page_last               207
_journal_paper_doi               10.1021/ic970381q
_journal_volume                  37
_journal_year                    1998
_chemical_formula_sum            'C19 H21 Cl2 N5 O10 Zn'
_chemical_formula_weight         615.68
_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     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 96.465(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3247(11)
_cell_length_b                   11.0320(12)
_cell_length_c                   20.761(2)
_cell_measurement_reflns_used    6644
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.09
_cell_volume                     2349.7(4)
_computing_cell_refinement       'local programs'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      160(2)
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13943
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.340
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_description       prism
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.164
_refine_diff_density_min         -1.073
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.093
_refine_ls_goodness_of_fit_obs   1.084
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5336
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.096
_refine_ls_restrained_S_obs      1.084
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_obs          0.0554
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0427P)²+9.4855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1407
_refine_ls_wR_factor_obs         0.1216
_reflns_number_observed          4146
_reflns_number_total             5340
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic970381q_1.cif
_cod_data_source_block           jcl55
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+9.4855P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+9.4855P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4322601
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_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Zn Zn 0.31309(4) 0.35991(4) 0.37686(2) 0.02017(14) Uani 1 d . .
O1 O 0.3327(3) 0.5144(3) 0.30584(13) 0.0234(6) Uani 1 d . .
N1 N 0.4814(3) 0.4418(3) 0.4084(2) 0.0208(7) Uani 1 d . .
N2 N 0.6360(3) 0.5802(3) 0.4027(2) 0.0241(7) Uani 1 d . .
H2 H 0.6763(3) 0.6444(3) 0.3895(2) 0.029 Uiso 1 calc R .
N3 N 0.1296(3) 0.4060(3) 0.3441(2) 0.0200(7) Uani 1 d . .
N4 N -0.0167(3) 0.4938(3) 0.2720(2) 0.0230(7) Uani 1 d . .
C1 C 0.5849(4) 0.4156(4) 0.4561(2) 0.0214(8) Uani 1 d . .
C2 C 0.6017(4) 0.3209(4) 0.5009(2) 0.0243(8) Uani 1 d . .
H2A H 0.5361(4) 0.2614(4) 0.5038(2) 0.029 Uiso 1 calc R .
C3 C 0.7183(4) 0.3178(4) 0.5411(2) 0.0288(9) Uani 1 d . .
H3 H 0.7329(4) 0.2545(4) 0.5721(2) 0.035 Uiso 1 calc R .
C4 C 0.8161(4) 0.4062(4) 0.5372(2) 0.0309(10) Uani 1 d . .
H4 H 0.8948(4) 0.4009(4) 0.5655(2) 0.037 Uiso 1 calc R .
C5 C 0.8000(4) 0.4998(4) 0.4933(2) 0.0287(9) Uani 1 d . .
H5 H 0.8655(4) 0.5595(4) 0.4906(2) 0.034 Uiso 1 calc R .
C6 C 0.6822(4) 0.5029(4) 0.4525(2) 0.0233(8) Uani 1 d . .
C7 C 0.5184(4) 0.5394(4) 0.3781(2) 0.0221(8) Uani 1 d . .
C8 C 0.4360(4) 0.5965(4) 0.3223(2) 0.0248(9) Uani 1 d . .
H8A H 0.4022(4) 0.6760(4) 0.3350(2) 0.030 Uiso 1 calc R .
H8B H 0.4871(4) 0.6087(4) 0.2852(2) 0.030 Uiso 1 calc R .
C9 C 0.2147(4) 0.5627(4) 0.2740(2) 0.0252(9) Uani 1 d . .
H9A H 0.2139(4) 0.5577(4) 0.2264(2) 0.030 Uiso 1 calc R .
H9B H 0.2039(4) 0.6484(4) 0.2864(2) 0.030 Uiso 1 calc R .
C10 C 0.1093(4) 0.4861(4) 0.2963(2) 0.0211(8) Uani 1 d . .
C11 C -0.0728(5) 0.5725(4) 0.2199(2) 0.0334(10) Uani 1 d . .
H11A H -0.1259(27) 0.6351(19) 0.2377(3) 0.050 Uiso 1 calc R .
H11B H -0.1276(26) 0.5244(7) 0.1878(8) 0.050 Uiso 1 calc R .
H11C H -0.0027(5) 0.6110(24) 0.1991(11) 0.050 Uiso 1 calc R .
C12 C -0.0846(4) 0.4125(4) 0.3062(2) 0.0218(8) Uani 1 d . .
C13 C -0.2168(4) 0.3822(4) 0.2994(2) 0.0271(9) Uani 1 d . .
H13 H -0.2776(4) 0.4192(4) 0.2677(2) 0.033 Uiso 1 calc R .
C14 C -0.2540(4) 0.2953(4) 0.3415(2) 0.0292(9) Uani 1 d . .
H14 H -0.3428(4) 0.2710(4) 0.3386(2) 0.035 Uiso 1 calc R .
C15 C -0.1630(4) 0.2421(4) 0.3887(2) 0.0287(10) Uani 1 d . .
H15 H -0.1923(4) 0.1833(4) 0.4172(2) 0.034 Uiso 1 calc R .
C16 C -0.0324(4) 0.2727(4) 0.3949(2) 0.0253(9) Uani 1 d . .
H16 H 0.0282(4) 0.2365(4) 0.4271(2) 0.030 Uiso 1 calc R .
C17 C 0.0067(4) 0.3586(4) 0.3520(2) 0.0210(8) Uani 1 d . .
O2 O 0.3654(3) 0.2471(3) 0.30608(14) 0.0273(6) Uani 1 d D .
H2B H 0.4122(44) 0.1789(27) 0.3138(26) 0.041 Uiso 1 d D .
H2C H 0.3845(50) 0.2758(46) 0.2678(13) 0.041 Uiso 1 d D .
N5 N 0.2932(4) 0.2177(3) 0.4392(2) 0.0278(8) Uani 1 d . .
C18 C 0.2712(4) 0.1281(4) 0.4620(2) 0.0279(9) Uani 1 d . .
C19 C 0.2384(6) 0.0131(4) 0.4901(3) 0.0443(13) Uani 1 d . .
H19A H 0.2184(37) 0.0262(7) 0.5346(7) 0.066 Uiso 1 calc R .
H19B H 0.3124(15) -0.0426(12) 0.4905(17) 0.066 Uiso 1 calc R .
H19C H 0.1623(23) -0.0220(17) 0.4643(11) 0.066 Uiso 1 calc R .
Cl1 Cl 0.50464(10) 0.44182(10) 0.14941(6) 0.0328(3) Uani 1 d . .
O3 O 0.4389(7) 0.5517(5) 0.1504(3) 0.101(2) Uani 1 d . .
O4 O 0.6383(4) 0.4609(7) 0.1469(3) 0.121(3) Uani 1 d . .
O5 O 0.4564(6) 0.3706(5) 0.0969(2) 0.086(2) Uani 1 d . .
O6 O 0.4930(4) 0.3770(4) 0.2096(2) 0.0544(10) Uani 1 d . .
Cl2 Cl 0.90464(12) 0.80402(11) 0.36807(6) 0.0392(3) Uani 1 d . .
O7 O 0.7935(5) 0.7533(6) 0.3270(3) 0.099(2) Uani 1 d . .
O8 O 0.8950(6) 0.7568(5) 0.4309(3) 0.087(2) Uani 1 d . .
O9 O 0.8912(5) 0.9304(4) 0.3688(3) 0.079(2) Uani 1 d . .
O10 O 1.0230(4) 0.7690(4) 0.3442(2) 0.0551(11) Uani 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
N1 Zn N3 138.49(14) . . ?
N1 Zn O2 102.72(13) . . ?
N3 Zn O2 103.07(13) . . ?
N1 Zn N5 106.39(14) . . ?
N3 Zn N5 104.45(14) . . ?
O2 Zn N5 92.37(14) . . ?
N1 Zn O1 74.76(12) . . ?
N3 Zn O1 74.92(12) . . ?
O2 Zn O1 86.58(11) . . ?
N5 Zn O1 178.60(13) . . ?
C8 O1 C9 117.2(3) . . ?
C8 O1 Zn 116.3(2) . . ?
C9 O1 Zn 116.5(2) . . ?
C7 N1 C1 105.4(3) . . ?
C7 N1 Zn 119.8(3) . . ?
C1 N1 Zn 134.6(3) . . ?
C7 N2 C6 107.4(3) . . ?
C10 N3 C17 105.5(3) . . ?
C10 N3 Zn 119.1(3) . . ?
C17 N3 Zn 134.4(3) . . ?
C10 N4 C12 106.9(3) . . ?
C10 N4 C11 127.2(4) . . ?
C12 N4 C11 125.9(4) . . ?
C2 C1 C6 120.9(4) . . ?
C2 C1 N1 130.7(4) . . ?
C6 C1 N1 108.4(3) . . ?
C3 C2 C1 117.0(4) . . ?
C2 C3 C4 121.8(4) . . ?
C5 C4 C3 121.5(4) . . ?
C4 C5 C6 116.8(4) . . ?
N2 C6 C1 105.9(3) . . ?
N2 C6 C5 132.0(4) . . ?
C1 C6 C5 122.1(4) . . ?
N1 C7 N2 112.9(4) . . ?
N1 C7 C8 122.7(4) . . ?
N2 C7 C8 124.4(4) . . ?
O1 C8 C7 105.4(3) . . ?
O1 C9 C10 105.2(3) . . ?
N3 C10 N4 112.8(4) . . ?
N3 C10 C9 123.2(4) . . ?
N4 C10 C9 123.9(3) . . ?
N4 C12 C17 106.5(3) . . ?
N4 C12 C13 130.5(4) . . ?
C17 C12 C13 123.0(4) . . ?
C14 C13 C12 116.1(4) . . ?
C13 C14 C15 121.2(4) . . ?
C16 C15 C14 122.1(4) . . ?
C15 C16 C17 117.2(4) . . ?
C16 C17 C12 120.3(4) . . ?
C16 C17 N3 131.5(4) . . ?
C12 C17 N3 108.2(3) . . ?
C18 N5 Zn 165.6(4) . . ?
N5 C18 C19 178.1(5) . . ?
O5 Cl1 O3 111.9(3) . . ?
O5 Cl1 O4 108.8(4) . . ?
O3 Cl1 O4 110.7(5) . . ?
O5 Cl1 O6 109.7(3) . . ?
O3 Cl1 O6 109.1(3) . . ?
O4 Cl1 O6 106.4(3) . . ?
O9 Cl2 O8 109.8(3) . . ?
O9 Cl2 O10 111.3(3) . . ?
O8 Cl2 O10 111.9(3) . . ?
O9 Cl2 O7 108.4(4) . . ?
O8 Cl2 O7 105.3(4) . . ?
O10 Cl2 O7 110.0(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn N1 2.002(3) . ?
Zn N3 2.005(3) . ?
Zn O2 2.044(3) . ?
Zn N5 2.059(4) . ?
Zn O1 2.278(3) . ?
O1 C8 1.412(5) . ?
O1 C9 1.422(5) . ?
N1 C7 1.325(5) . ?
N1 C1 1.403(5) . ?
N2 C7 1.340(5) . ?
N2 C6 1.384(5) . ?
N3 C10 1.328(5) . ?
N3 C17 1.400(5) . ?
N4 C10 1.343(5) . ?
N4 C12 1.384(5) . ?
N4 C11 1.455(5) . ?
C1 C2 1.396(6) . ?
C1 C6 1.399(6) . ?
C2 C3 1.386(6) . ?
C3 C4 1.413(7) . ?
C4 C5 1.375(7) . ?
C5 C6 1.401(6) . ?
C7 C8 1.497(6) . ?
C9 C10 1.491(6) . ?
C12 C17 1.394(6) . ?
C12 C13 1.397(6) . ?
C13 C14 1.381(6) . ?
C14 C15 1.407(6) . ?
C15 C16 1.383(6) . ?
C16 C17 1.390(6) . ?
N5 C18 1.130(6) . ?
C18 C19 1.453(6) . ?
Cl1 O5 1.390(4) . ?
Cl1 O3 1.391(4) . ?
Cl1 O4 1.403(4) . ?
Cl1 O6 1.456(4) . ?
Cl2 O9 1.401(4) . ?
Cl2 O8 1.418(5) . ?
Cl2 O10 1.423(4) . ?
Cl2 O7 1.462(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168337482
