#------------------------------------------------------------------------------
#$Date: 2019-06-05 06:55:19 +0300 (Wed, 05 Jun 2019) $
#$Revision: 215708 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/28/7232863.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_7232863
loop_
_publ_author_name
'Dong, Jun-Liang'
'Zhu, Peng-Yin'
'Du, Jia-Qiang'
'Xie, Fei'
'Lan, Hai-Ming'
'Yang, Ru-Xia'
'Yang, Li-Zheng'
'Wang, Duo-Zhi'
_publ_section_title
;
 Syntheses, structures, and magnetic properties of mixed-ligand complexes
 based on 3,6-bis(benzimidazol-1-yl)pyridazine
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              17560
_journal_paper_doi               10.1039/C9RA03082D
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C24 H16 N6 Ni O5 S'
_chemical_formula_sum            'C24 H16 N6 Ni O5 S'
_chemical_formula_weight         559.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-10-18 deposited with the CCDC.    2019-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 121.201(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.039(5)
_cell_length_b                   18.606(7)
_cell_length_c                   10.943(6)
_cell_measurement_reflns_used    2479
_cell_measurement_temperature    170.15
_cell_measurement_theta_max      25.87
_cell_measurement_theta_min      2.27
_cell_volume                     2270.8(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.15
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7171
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.698
_diffrn_reflns_theta_min         2.129
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.998
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0704 before and 0.0501 after correction. The Ratio of minimum to maximum transmission is 0.9100. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 1367 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         3970
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0571P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                3663
_reflns_number_total             3970
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra03082d2.cif
_cod_data_source_block           111
_cod_database_code               7232863
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.803
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.547(19)
 0.453(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Rotating group:
 O1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Ni1 Ni 0.41047(4) 0.73386(3) -0.04119(5) 0.01230(18) Uani 1 1 d .
S1 S 0.11567(12) 0.76775(8) 0.19230(14) 0.0197(3) Uani 1 1 d .
O1 O 0.2395(3) 0.7018(2) -0.1867(4) 0.0192(8) Uani 1 1 d .
H1A H 0.2594 0.6692 -0.1895 0.029 Uiso 1 1 d GR
H1B H 0.2102 0.7270 -0.2666 0.029 Uiso 1 1 d GR
O2 O 0.3756(3) 0.7556(2) 0.1164(4) 0.0179(9) Uani 1 1 d .
O3 O 0.1750(4) 0.7626(2) -0.0262(5) 0.0255(10) Uani 1 1 d .
O4 O -0.0270(3) 0.7823(2) 0.3226(4) 0.0189(9) Uani 1 1 d .
O5 O 0.1083(3) 0.7510(2) 0.5421(4) 0.0172(8) Uani 1 1 d .
N1 N 0.4554(4) 0.6318(3) 0.0484(5) 0.0177(10) Uani 1 1 d .
N2 N 0.5251(4) 0.5523(3) 0.2264(5) 0.0195(10) Uani 1 1 d .
N3 N 0.6282(4) 0.4585(3) 0.3797(5) 0.0236(11) Uani 1 1 d .
N4 N 0.6985(4) 0.4310(3) 0.5103(5) 0.0225(11) Uani 1 1 d .
N5 N 0.8061(4) 0.4370(3) 0.7550(5) 0.0183(10) Uani 1 1 d .
N6 N 0.8777(4) 0.3415(3) 0.8992(5) 0.0173(10) Uani 1 1 d .
C00R C 0.0806(5) 0.7674(3) 0.4154(6) 0.0160(11) Uani 1 1 d .
C1 C 0.2705(6) 0.7615(3) 0.0937(6) 0.0182(13) Uani 1 1 d .
C2 C 0.2589(5) 0.7666(3) 0.2205(6) 0.0159(11) Uani 1 1 d .
C3 C 0.3424(5) 0.7671(3) 0.3621(6) 0.0162(11) Uani 1 1 d .
H3 H 0.4263 0.7679 0.3987 0.019 Uiso 1 1 calc R
C4 C 0.2926(5) 0.7663(3) 0.4499(6) 0.0187(12) Uani 1 1 d .
H4 H 0.3390 0.7652 0.5513 0.022 Uiso 1 1 calc R
C5 C 0.1698(5) 0.7672(3) 0.3726(6) 0.0150(11) Uani 1 1 d .
C6 C 0.5196(5) 0.6225(3) 0.1859(6) 0.0160(11) Uani 1 1 d .
H6 H 0.5588 0.6607 0.2518 0.019 Uiso 1 1 calc R
C7 C 0.4140(5) 0.5638(3) -0.0091(5) 0.0175(12) Uani 1 1 d .
C8 C 0.3420(5) 0.5431(3) -0.1524(6) 0.0229(13) Uani 1 1 d .
H8 H 0.3148 0.5771 -0.2278 0.028 Uiso 1 1 calc R
C9 C 0.3126(5) 0.4719(3) -0.1789(7) 0.0273(14) Uani 1 1 d .
H9 H 0.2656 0.4560 -0.2750 0.033 Uiso 1 1 calc R
C10 C 0.3498(6) 0.4217(4) -0.0683(7) 0.0311(15) Uani 1 1 d .
H10 H 0.3259 0.3729 -0.0916 0.037 Uiso 1 1 calc R
C11 C 0.4207(6) 0.4412(3) 0.0743(7) 0.0258(13) Uani 1 1 d .
H11 H 0.4447 0.4077 0.1499 0.031 Uiso 1 1 calc R
C12 C 0.4542(5) 0.5133(3) 0.0988(6) 0.0186(12) Uani 1 1 d .
C13 C 0.5946(5) 0.5269(3) 0.3678(6) 0.0161(11) Uani 1 1 d .
C14 C 0.6249(5) 0.5721(3) 0.4828(6) 0.0220(12) Uani 1 1 d .
H14 H 0.5962 0.6201 0.4694 0.026 Uiso 1 1 calc R
C15 C 0.6983(5) 0.5439(3) 0.6165(6) 0.0224(13) Uani 1 1 d .
H15 H 0.7241 0.5716 0.7004 0.027 Uiso 1 1 calc R
C16 C 0.7328(5) 0.4725(3) 0.6229(6) 0.0202(12) Uani 1 1 d .
C17 C 0.8100(5) 0.3634(3) 0.7670(6) 0.0189(11) Uani 1 1 d .
H17 H 0.7680 0.3318 0.6880 0.023 Uiso 1 1 calc R
C18 C 0.9208(5) 0.4035(3) 0.9807(6) 0.0196(12) Uani 1 1 d .
C19 C 0.9945(5) 0.4109(4) 1.1297(6) 0.0257(14) Uani 1 1 d .
H19 H 1.0215 0.3702 1.1910 0.031 Uiso 1 1 calc R
C20 C 1.0256(5) 0.4791(4) 1.1822(7) 0.0306(15) Uani 1 1 d .
H20 H 1.0752 0.4859 1.2824 0.037 Uiso 1 1 calc R
C21 C 0.9867(6) 0.5392(4) 1.0927(7) 0.0327(16) Uani 1 1 d .
H21 H 1.0113 0.5855 1.1343 0.039 Uiso 1 1 calc R
C22 C 0.9139(6) 0.5338(3) 0.9467(8) 0.0271(14) Uani 1 1 d .
H22 H 0.8890 0.5748 0.8863 0.032 Uiso 1 1 calc R
C23 C 0.8788(5) 0.4638(3) 0.8925(6) 0.0199(12) 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'
Ni Ni 0.3393 1.1124 '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'
S S 0.1246 0.1234 '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
O1 Ni1 O4 94.26(16) . 4_564
O1 Ni1 O5 154.76(15) . 4_564
O1 Ni1 N1 91.61(17) . .
O1 Ni1 N6 94.15(17) . 3_454
O1 Ni1 C00R 124.50(17) . 4_564
O2 Ni1 O1 94.93(16) . .
O2 Ni1 O4 170.79(15) . 4_564
O2 Ni1 O5 109.95(15) . 4_564
O2 Ni1 N1 85.07(18) . .
O2 Ni1 N6 88.51(17) . 3_454
O2 Ni1 C00R 140.51(17) . 4_564
O4 Ni1 O5 60.91(15) 4_564 4_564
O4 Ni1 N1 95.05(18) 4_564 .
O4 Ni1 N6 90.46(17) 4_564 3_454
O4 Ni1 C00R 30.34(17) 4_564 4_564
O5 Ni1 C00R 30.58(17) 4_564 4_564
N1 Ni1 O5 86.54(16) . 4_564
N1 Ni1 N6 171.72(18) . 3_454
N1 Ni1 C00R 91.18(18) . 4_564
N6 Ni1 O5 90.76(16) 3_454 4_564
N6 Ni1 C00R 90.45(18) 3_454 4_564
C5 S1 C2 91.8(3) . .
C1 O2 Ni1 123.0(4) . .
C00R O4 Ni1 94.4(4) . 4_465
C00R O5 Ni1 84.9(3) . 4_465
C6 N1 Ni1 121.6(4) . .
C6 N1 C7 105.6(5) . .
C7 N1 Ni1 132.0(3) . .
C6 N2 C12 105.8(5) . .
C6 N2 C13 124.8(5) . .
C13 N2 C12 129.2(5) . .
C13 N3 N4 118.7(5) . .
C16 N4 N3 119.1(5) . .
C17 N5 C16 122.3(5) . .
C17 N5 C23 106.4(5) . .
C23 N5 C16 131.2(5) . .
C17 N6 Ni1 123.9(4) . 3_546
C17 N6 C18 105.5(5) . .
C18 N6 Ni1 130.6(3) . 3_546
O4 C00R Ni1 55.3(3) . 4_465
O4 C00R O5 119.8(5) . .
O4 C00R C5 118.5(5) . .
O5 C00R Ni1 64.5(3) . 4_465
O5 C00R C5 121.6(5) . .
C5 C00R Ni1 173.4(4) . 4_465
O2 C1 C2 116.7(5) . .
O3 C1 O2 126.3(6) . .
O3 C1 C2 117.0(6) . .
C1 C2 S1 117.4(4) . .
C3 C2 S1 110.9(4) . .
C3 C2 C1 131.5(6) . .
C2 C3 C4 113.4(5) . .
C5 C4 C3 112.5(5) . .
C00R C5 S1 116.5(4) . .
C4 C5 S1 111.3(4) . .
C4 C5 C00R 132.2(5) . .
N1 C6 N2 113.3(5) . .
N1 C7 C8 129.3(5) . .
C12 C7 N1 110.2(4) . .
C12 C7 C8 120.5(5) . .
C9 C8 C7 117.0(6) . .
C8 C9 C10 122.0(6) . .
C11 C10 C9 121.8(6) . .
C10 C11 C12 115.3(6) . .
C7 C12 N2 105.1(5) . .
C7 C12 C11 123.2(5) . .
C11 C12 N2 131.6(5) . .
N3 C13 N2 114.9(5) . .
N3 C13 C14 124.4(5) . .
C14 C13 N2 120.7(5) . .
C15 C14 C13 116.7(5) . .
C14 C15 C16 116.5(5) . .
N4 C16 N5 113.7(5) . .
N4 C16 C15 124.5(5) . .
C15 C16 N5 121.7(5) . .
N6 C17 N5 112.7(5) . .
N6 C18 C19 129.2(5) . .
N6 C18 C23 110.0(5) . .
C23 C18 C19 120.8(5) . .
C20 C19 C18 117.0(6) . .
C19 C20 C21 121.9(6) . .
C22 C21 C20 122.5(6) . .
C21 C22 C23 115.8(6) . .
N5 C23 C18 105.3(5) . .
N5 C23 C22 132.8(5) . .
C18 C23 C22 121.9(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 2.045(4) .
Ni1 O2 2.038(4) .
Ni1 O4 2.059(4) 4_564
Ni1 O5 2.264(4) 4_564
Ni1 N1 2.077(5) .
Ni1 N6 2.080(5) 3_454
Ni1 C00R 2.497(6) 4_564
S1 C2 1.729(6) .
S1 C5 1.718(6) .
O2 C1 1.266(8) .
O3 C1 1.257(7) .
O4 Ni1 2.059(4) 4_465
O4 C00R 1.265(7) .
O5 Ni1 2.264(4) 4_465
O5 C00R 1.276(7) .
N1 C6 1.300(6) .
N1 C7 1.392(7) .
N2 C6 1.370(7) .
N2 C12 1.411(7) .
N2 C13 1.409(7) .
N3 N4 1.337(6) .
N3 C13 1.330(7) .
N4 C16 1.320(8) .
N5 C16 1.417(7) .
N5 C17 1.375(7) .
N5 C23 1.390(7) .
N6 Ni1 2.080(5) 3_546
N6 C17 1.310(7) .
N6 C18 1.387(7) .
C00R Ni1 2.497(6) 4_465
C00R C5 1.462(8) .
C1 C2 1.474(8) .
C2 C3 1.356(8) .
C3 C4 1.412(8) .
C4 C5 1.369(8) .
C7 C8 1.401(8) .
C7 C12 1.382(8) .
C8 C9 1.368(9) .
C9 C10 1.402(9) .
C10 C11 1.388(9) .
C11 C12 1.394(8) .
C13 C14 1.390(8) .
C14 C15 1.372(8) .
C15 C16 1.393(8) .
C18 C19 1.406(7) .
C18 C23 1.394(8) .
C19 C20 1.365(9) .
C20 C21 1.397(10) .
C21 C22 1.376(9) .
C22 C23 1.406(8) .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.547(19)
2 0.453(19)
