#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/40/4324006.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_4324006
loop_
_publ_author_name
'Craig J. Matthews'
'Troy A. Leese'
'William Clegg'
'Mark R. J. Elsegood'
'Lynne Horsburgh'
'Joyce C. Lockhart'
_publ_section_title
;
 A Route to Bis(benzimidazole) Ligands with Built-In Asymmetry: Potential
 Models of Protein Binding Sites Having Histidines of Different Basicity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7563
_journal_page_last               7571
_journal_paper_doi               10.1021/ic960777m
_journal_volume                  35
_journal_year                    1996
_chemical_formula_sum            'C20 H23 Cl2 Cu N5 O10'
_chemical_formula_weight         627.87
_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   'goem except H2B&C coords refined'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'all non-H atoms found by direct methods'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 105.960(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2168(7)
_cell_length_b                   30.740(2)
_cell_length_c                   8.3403(6)
_cell_measurement_reflns_used    9009
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      2.17
_cell_volume                     2518.4(3)
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            13770
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.32
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.144
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_description       block
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         2.198
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.077
_refine_ls_goodness_of_fit_obs   1.114
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4418
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.085
_refine_ls_restrained_S_obs      1.114
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_obs          0.0528
_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)+(0.0581P)²+6.8432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1360
_refine_ls_wR_factor_obs         0.1306
_reflns_number_observed          3915
_reflns_number_total             4432
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic960777m_1.cif
_cod_data_source_block           complex-A
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+6.8432P] 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^)+(0.0581P)^2^+6.8432P] 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               4324006
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
Cu Cu 0.84189(5) 0.123154(15) 0.27168(6) 0.0297(2) Uani 1 d . .
O1 O 0.9816(3) 0.14804(9) 0.4846(3) 0.0315(6) Uani 1 d . .
N1 N 0.9615(3) 0.07337(10) 0.3358(4) 0.0270(7) Uani 1 d . .
N2 N 1.1580(3) 0.04627(11) 0.4789(4) 0.0324(8) Uani 1 d . .
H2 H 1.2384(3) 0.04466(11) 0.5522(4) 0.039 Uiso 1 calc R .
N3 N 0.7915(3) 0.18382(12) 0.2536(4) 0.0333(8) Uani 1 d . .
N4 N 0.8415(4) 0.25248(11) 0.3225(4) 0.0348(8) Uani 1 d . .
H4 H 0.8846(4) 0.27524(11) 0.3761(4) 0.042 Uiso 1 calc R .
C1 C 0.9704(4) 0.03105(12) 0.2782(5) 0.0288(8) Uani 1 d . .
C2 C 0.8798(5) 0.00648(14) 0.1584(5) 0.0362(9) Uani 1 d . .
H2A H 0.7944(5) 0.01792(14) 0.0970(5) 0.043 Uiso 1 calc R .
C3 C 0.9187(5) -0.03528(15) 0.1318(6) 0.0434(11) Uani 1 d . .
H3 H 0.8591(5) -0.05298(15) 0.0501(6) 0.052 Uiso 1 calc R .
C4 C 1.0453(5) -0.05210(14) 0.2238(6) 0.0427(11) Uani 1 d . .
H4A H 1.0690(5) -0.08099(14) 0.2023(6) 0.051 Uiso 1 calc R .
C5 C 1.1355(5) -0.02817(14) 0.3431(6) 0.0397(10) Uani 1 d . .
H5 H 1.2208(5) -0.03974(14) 0.4043(6) 0.048 Uiso 1 calc R .
C6 C 1.0962(4) 0.01378(13) 0.3703(5) 0.0311(9) Uani 1 d . .
C7 C 1.0749(4) 0.08053(13) 0.4538(5) 0.0298(8) Uani 1 d . .
C8 C 1.1042(4) 0.12304(13) 0.5425(5) 0.0334(9) Uani 1 d . .
H8A H 1.1269(4) 0.11877(13) 0.6647(5) 0.040 Uiso 1 calc R .
H8B H 1.1814(4) 0.13784(13) 0.5152(5) 0.040 Uiso 1 calc R .
C9 C 0.9982(5) 0.19429(13) 0.4857(5) 0.0370(9) Uani 1 d . .
H9A H 1.0835(5) 0.20221(13) 0.4584(5) 0.044 Uiso 1 calc R .
H9B H 1.0009(5) 0.20640(13) 0.5966(5) 0.044 Uiso 1 calc R .
C10 C 0.8772(4) 0.21112(13) 0.3556(5) 0.0326(9) Uani 1 d . .
C11 C 0.7254(4) 0.25370(13) 0.1895(5) 0.0335(9) Uani 1 d . .
C12 C 0.6444(4) 0.28749(13) 0.1058(5) 0.0361(9) Uani 1 d . .
H12 H 0.6672(4) 0.31690(13) 0.1359(5) 0.043 Uiso 1 calc R .
C13 C 0.5308(5) 0.27756(14) -0.0211(5) 0.0369(10) Uani 1 d . .
C14 C 0.4969(4) 0.23311(14) -0.0657(5) 0.0350(9) Uani 1 d . .
C15 C 0.5784(4) 0.19987(13) 0.0174(5) 0.0322(9) Uani 1 d . .
H15 H 0.5568(4) 0.17039(13) -0.0127(5) 0.039 Uiso 1 calc R .
C16 C 0.6939(4) 0.21041(12) 0.1474(5) 0.0311(9) Uani 1 d . .
C17 C 0.4382(5) 0.3135(2) -0.1090(6) 0.0463(11) Uani 1 d . .
H17A H 0.3457(9) 0.3082(6) -0.1008(38) 0.069 Uiso 1 calc R .
H17B H 0.4377(28) 0.3142(7) -0.2267(11) 0.069 Uiso 1 calc R .
H17C H 0.4712(21) 0.3414(2) -0.0567(28) 0.069 Uiso 1 calc R .
C18 C 0.3694(4) 0.2226(2) -0.2020(6) 0.0407(10) Uani 1 d . .
H18A H 0.3671(17) 0.2401(8) -0.3010(15) 0.061 Uiso 1 calc R .
H18B H 0.2894(4) 0.2293(10) -0.1634(15) 0.061 Uiso 1 calc R .
H18C H 0.3691(16) 0.1917(3) -0.2302(28) 0.061 Uiso 1 calc R .
O2 O 0.7911(3) 0.11370(11) 0.0226(4) 0.0433(8) Uani 1 d D .
H2B H 0.8427(50) 0.1280(17) -0.0316(65) 0.065 Uiso 1 d D .
H2C H 0.7336(45) 0.0936(14) -0.0355(62) 0.065 Uiso 1 d D .
N5 N 0.6568(4) 0.09539(12) 0.2900(5) 0.0393(8) Uani 1 d . .
C19 C 0.5508(4) 0.08145(14) 0.2605(5) 0.0344(9) Uani 1 d . .
C20 C 0.4139(5) 0.0641(2) 0.2193(6) 0.0455(11) Uani 1 d . .
H20A H 0.4085(10) 0.0413(8) 0.2996(26) 0.068 Uiso 1 calc R .
H20B H 0.3908(14) 0.0517(10) 0.1067(18) 0.068 Uiso 1 calc R .
H20C H 0.3497(6) 0.0874(3) 0.2237(43) 0.068 Uiso 1 calc R .
Cl1 Cl 0.49555(10) 0.06821(4) -0.25526(14) 0.0411(3) Uani 1 d . .
O3 O 0.5812(6) 0.0940(2) -0.3296(8) 0.106(2) Uani 1 d . .
O4 O 0.3855(4) 0.0925(2) -0.2371(7) 0.097(2) Uani 1 d . .
O5 O 0.4470(5) 0.03234(15) -0.3621(6) 0.092(2) Uani 1 d . .
O6 O 0.5789(4) 0.05270(15) -0.1007(5) 0.0769(13) Uani 1 d . .
Cl2 Cl 0.09846(10) 0.33132(3) -0.46481(12) 0.0311(2) Uani 1 d . .
O7 O 0.2076(4) 0.34870(14) -0.5170(5) 0.0685(11) Uani 1 d . .
O8 O 0.1141(4) 0.28596(12) -0.4362(6) 0.0783(14) Uani 1 d . .
O9 O 0.0884(4) 0.35340(14) -0.3201(4) 0.0600(10) Uani 1 d . .
O10 O -0.0272(3) 0.33779(10) -0.5991(4) 0.0439(8) 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'
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
_geom_angle_publ_flag
N3 Cu N1 156.71(14) . . ?
N3 Cu O2 94.09(14) . . ?
N1 Cu O2 97.70(14) . . ?
N3 Cu O1 79.53(12) . . ?
N1 Cu O1 79.83(12) . . ?
O2 Cu O1 147.96(12) . . ?
N3 Cu N5 99.82(14) . . ?
N1 Cu N5 99.77(14) . . ?
O2 Cu N5 91.97(14) . . ?
O1 Cu N5 120.02(13) . . ?
C9 O1 C8 116.0(3) . . ?
C9 O1 Cu 114.9(2) . . ?
C8 O1 Cu 114.7(2) . . ?
C7 N1 C1 106.6(3) . . ?
C7 N1 Cu 115.6(3) . . ?
C1 N1 Cu 137.3(3) . . ?
C7 N2 C6 108.2(3) . . ?
C10 N3 C16 105.3(3) . . ?
C10 N3 Cu 116.3(3) . . ?
C16 N3 Cu 137.9(3) . . ?
C10 N4 C11 108.5(3) . . ?
C2 C1 N1 131.4(4) . . ?
C2 C1 C6 121.1(4) . . ?
N1 C1 C6 107.4(3) . . ?
C3 C2 C1 117.3(4) . . ?
C2 C3 C4 121.0(4) . . ?
C5 C4 C3 122.1(4) . . ?
C4 C5 C6 116.8(4) . . ?
N2 C6 C5 132.8(4) . . ?
N2 C6 C1 105.6(3) . . ?
C5 C6 C1 121.5(4) . . ?
N1 C7 N2 112.1(3) . . ?
N1 C7 C8 122.2(4) . . ?
N2 C7 C8 125.6(4) . . ?
O1 C8 C7 105.3(3) . . ?
O1 C9 C10 105.4(3) . . ?
N4 C10 N3 112.0(4) . . ?
N4 C10 C9 127.3(4) . . ?
N3 C10 C9 120.7(4) . . ?
N4 C11 C12 133.1(4) . . ?
N4 C11 C16 105.3(4) . . ?
C12 C11 C16 121.6(4) . . ?
C13 C12 C11 118.8(4) . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 C17 119.8(4) . . ?
C14 C13 C17 119.9(4) . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 C18 119.8(4) . . ?
C13 C14 C18 119.7(4) . . ?
C14 C15 C16 118.7(4) . . ?
C11 C16 N3 108.9(4) . . ?
C11 C16 C15 120.2(4) . . ?
N3 C16 C15 130.9(4) . . ?
C19 N5 Cu 163.8(4) . . ?
N5 C19 C20 178.8(5) . . ?
O4 Cl1 O6 112.5(3) . . ?
O4 Cl1 O5 109.3(3) . . ?
O6 Cl1 O5 109.2(3) . . ?
O4 Cl1 O3 110.9(3) . . ?
O6 Cl1 O3 107.0(3) . . ?
O5 Cl1 O3 107.8(4) . . ?
O7 Cl2 O9 109.4(2) . . ?
O7 Cl2 O8 111.3(3) . . ?
O9 Cl2 O8 111.1(3) . . ?
O7 Cl2 O10 108.3(2) . . ?
O9 Cl2 O10 109.5(2) . . ?
O8 Cl2 O10 107.3(2) . . ?
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
Cu N3 1.930(4) . ?
Cu N1 1.940(3) . ?
Cu O2 2.019(3) . ?
Cu O1 2.093(3) . ?
Cu N5 2.118(4) . ?
O1 C9 1.431(5) . ?
O1 C8 1.435(5) . ?
N1 C7 1.316(5) . ?
N1 C1 1.398(5) . ?
N2 C7 1.333(5) . ?
N2 C6 1.379(5) . ?
N3 C10 1.336(5) . ?
N3 C16 1.400(5) . ?
N4 C10 1.330(5) . ?
N4 C11 1.385(5) . ?
C1 C2 1.384(6) . ?
C1 C6 1.407(6) . ?
C2 C3 1.380(6) . ?
C3 C4 1.409(7) . ?
C4 C5 1.370(7) . ?
C5 C6 1.388(6) . ?
C7 C8 1.491(5) . ?
C9 C10 1.496(6) . ?
C11 C12 1.390(6) . ?
C11 C16 1.391(6) . ?
C12 C13 1.373(6) . ?
C13 C14 1.434(6) . ?
C13 C17 1.507(6) . ?
C14 C15 1.379(6) . ?
C14 C18 1.509(6) . ?
C15 C16 1.403(6) . ?
N5 C19 1.127(5) . ?
C19 C20 1.447(6) . ?
Cl1 O4 1.391(4) . ?
Cl1 O6 1.418(4) . ?
Cl1 O5 1.419(4) . ?
Cl1 O3 1.441(5) . ?
Cl2 O7 1.409(4) . ?
Cl2 O9 1.413(3) . ?
Cl2 O8 1.416(4) . ?
Cl2 O10 1.467(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168337560
