#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/16/4501659.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_4501659
loop_
_publ_author_name
'Li, Cheng-Peng'
'Zhao, Xiao-Hu'
'Chen, Xu-Dong'
'Yu, Qian'
'Du, Miao'
_publ_section_title
;
 Metal-Involved Solvothermal Interconversions of Pyrazinyl Substituted
 Azole Derivatives: Controllability and Mechanism
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5034
_journal_paper_doi               10.1021/cg100200b
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C22 H16 Co N18 S2'
_chemical_formula_weight         655.58
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.041(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.146(2)
_cell_length_b                   9.251(2)
_cell_length_c                   15.856(4)
_cell_measurement_reflns_used    1707
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.99
_cell_measurement_theta_min      2.56
_cell_volume                     1328.4(5)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5646
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.764965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             666
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0342P)²+0.3800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                1936
_reflns_number_total             2341
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100200b_si_002.cif
_cod_data_source_block           7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NONE' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1328.5(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4501659
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Co1 Co 0.0000 0.5000 0.0000 0.02983(13) Uani 1 2 d S
S1 S -0.14384(8) 0.95787(7) 0.10984(5) 0.0578(2) Uani 1 1 d .
N1 N 0.11638(18) 0.60834(18) -0.09248(10) 0.0328(4) Uani 1 1 d .
N2 N 0.2881(2) 0.7526(2) -0.19705(12) 0.0449(5) Uani 1 1 d .
N3 N 0.21448(18) 0.52757(18) 0.06547(11) 0.0335(4) Uani 1 1 d .
N4 N 0.28512(19) 0.49544(18) 0.14463(11) 0.0362(4) Uani 1 1 d .
N5 N 0.43218(18) 0.62446(18) 0.07545(11) 0.0328(4) Uani 1 1 d .
N6 N 0.5528(2) 0.7028(2) 0.05077(12) 0.0464(5) Uani 1 1 d D
H6A H 0.6335 0.6809 0.0883 0.056 Uiso 1 1 d RD
H6B H 0.5352 0.7954 0.0641 0.056 Uiso 1 1 d RD
N7 N 0.6571(2) 0.6097(2) 0.22568(13) 0.0501(5) Uani 1 1 d .
N8 N 0.5861(2) 0.4605(2) 0.36808(12) 0.0526(5) Uani 1 1 d .
N9 N -0.0564(2) 0.6972(2) 0.04600(12) 0.0463(5) Uani 1 1 d .
C1 C 0.3410(2) 0.7200(2) -0.11621(14) 0.0391(5) Uani 1 1 d .
H1 H 0.4373 0.7461 -0.0949 0.047 Uiso 1 1 calc R
C2 C 0.1505(3) 0.7138(2) -0.22382(15) 0.0448(6) Uani 1 1 d .
H2 H 0.1099 0.7359 -0.2794 0.054 Uiso 1 1 calc R
C3 C 0.0645(2) 0.6413(2) -0.17228(13) 0.0401(5) Uani 1 1 d .
H3 H -0.0315 0.6153 -0.1941 0.048 Uiso 1 1 calc R
C4 C 0.2564(2) 0.6487(2) -0.06370(13) 0.0314(5) Uani 1 1 d .
C5 C 0.3034(2) 0.6034(2) 0.02397(12) 0.0307(4) Uani 1 1 d .
C6 C 0.4169(2) 0.5565(2) 0.15016(13) 0.0334(5) Uani 1 1 d .
C7 C 0.5263(2) 0.5467(2) 0.22636(13) 0.0351(5) Uani 1 1 d .
C8 C 0.4920(3) 0.4724(2) 0.29669(14) 0.0438(6) Uani 1 1 d .
H8 H 0.3996 0.4292 0.2939 0.053 Uiso 1 1 calc R
C9 C 0.7162(3) 0.5251(3) 0.36819(17) 0.0572(7) Uani 1 1 d .
H9 H 0.7852 0.5210 0.4171 0.069 Uiso 1 1 calc R
C10 C 0.7513(3) 0.5974(3) 0.29822(18) 0.0605(7) Uani 1 1 d .
H10 H 0.8442 0.6396 0.3012 0.073 Uiso 1 1 calc R
C11 C -0.0915(2) 0.8061(2) 0.07198(13) 0.0364(5) 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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
N9 Co1 N9 180.00(10) . 3_565
N9 Co1 N3 88.87(7) . .
N9 Co1 N3 91.13(7) 3_565 .
N9 Co1 N3 91.13(7) . 3_565
N9 Co1 N3 88.87(7) 3_565 3_565
N3 Co1 N3 180.0 . 3_565
N9 Co1 N1 90.05(7) . .
N9 Co1 N1 89.95(7) 3_565 .
N3 Co1 N1 76.47(6) . .
N3 Co1 N1 103.53(6) 3_565 .
N9 Co1 N1 89.95(7) . 3_565
N9 Co1 N1 90.05(7) 3_565 3_565
N3 Co1 N1 103.53(6) . 3_565
N3 Co1 N1 76.47(6) 3_565 3_565
N1 Co1 N1 180.00(6) . 3_565
C3 N1 C4 117.09(18) . .
C3 N1 Co1 127.42(14) . .
C4 N1 Co1 115.48(13) . .
C2 N2 C1 116.53(19) . .
C5 N3 N4 109.28(16) . .
C5 N3 Co1 114.60(13) . .
N4 N3 Co1 135.91(13) . .
C6 N4 N3 106.16(17) . .
C5 N5 C6 105.74(16) . .
C5 N5 N6 123.57(17) . .
C6 N5 N6 130.69(17) . .
N5 N6 H6A 107.3 . .
N5 N6 H6B 104.4 . .
H6A N6 H6B 102.4 . .
C7 N7 C10 115.2(2) . .
C8 N8 C9 115.9(2) . .
C11 N9 Co1 178.23(18) . .
N2 C1 C4 121.8(2) . .
N2 C1 H1 119.1 . .
C4 C1 H1 119.1 . .
N2 C2 C3 122.5(2) . .
N2 C2 H2 118.8 . .
C3 C2 H2 118.8 . .
N1 C3 C2 121.3(2) . .
N1 C3 H3 119.4 . .
C2 C3 H3 119.4 . .
N1 C4 C1 120.85(19) . .
N1 C4 C5 112.44(17) . .
C1 C4 C5 126.67(19) . .
N3 C5 N5 108.79(17) . .
N3 C5 C4 120.62(17) . .
N5 C5 C4 130.59(18) . .
N4 C6 N5 110.01(18) . .
N4 C6 C7 122.75(19) . .
N5 C6 C7 127.24(19) . .
N7 C7 C8 122.0(2) . .
N7 C7 C6 118.58(19) . .
C8 C7 C6 119.46(19) . .
N8 C8 C7 122.4(2) . .
N8 C8 H8 118.8 . .
C7 C8 H8 118.8 . .
N8 C9 C10 121.9(2) . .
N8 C9 H9 119.1 . .
C10 C9 H9 119.1 . .
N7 C10 C9 122.7(2) . .
N7 C10 H10 118.7 . .
C9 C10 H10 118.7 . .
N9 C11 S1 178.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 N9 2.0574(19) .
Co1 N9 2.0574(19) 3_565
Co1 N3 2.1027(17) .
Co1 N3 2.1027(17) 3_565
Co1 N1 2.1736(17) .
Co1 N1 2.1736(16) 3_565
S1 C11 1.625(2) .
N1 C3 1.323(3) .
N1 C4 1.351(3) .
N2 C2 1.320(3) .
N2 C1 1.340(3) .
N3 C5 1.318(2) .
N3 N4 1.362(2) .
N4 C6 1.323(3) .
N5 C5 1.350(2) .
N5 C6 1.366(3) .
N5 N6 1.420(2) .
N6 H6A 0.9037 .
N6 H6B 0.9022 .
N7 C7 1.333(3) .
N7 C10 1.342(3) .
N8 C8 1.327(3) .
N8 C9 1.331(3) .
N9 C11 1.151(3) .
C1 C4 1.381(3) .
C1 H1 0.9300 .
C2 C3 1.384(3) .
C2 H2 0.9300 .
C3 H3 0.9300 .
C4 C5 1.458(3) .
C6 C7 1.460(3) .
C7 C8 1.383(3) .
C8 H8 0.9300 .
C9 C10 1.371(4) .
C9 H9 0.9300 .
C10 H10 0.9300 .
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
N9 Co1 N1 C3 -94.33(18) .
N9 Co1 N1 C3 85.67(18) 3_565
N3 Co1 N1 C3 176.85(18) .
N3 Co1 N1 C3 -3.15(18) 3_565
N9 Co1 N1 C4 84.14(14) .
N9 Co1 N1 C4 -95.86(14) 3_565
N3 Co1 N1 C4 -4.68(13) .
N3 Co1 N1 C4 175.32(13) 3_565
N9 Co1 N3 C5 -84.69(15) .
N9 Co1 N3 C5 95.31(15) 3_565
N1 Co1 N3 C5 5.64(14) .
N1 Co1 N3 C5 -174.36(14) 3_565
N9 Co1 N3 N4 89.27(19) .
N9 Co1 N3 N4 -90.73(19) 3_565
N1 Co1 N3 N4 179.6(2) .
N1 Co1 N3 N4 -0.4(2) 3_565
C5 N3 N4 C6 1.4(2) .
Co1 N3 N4 C6 -172.80(15) .
C2 N2 C1 C4 0.4(3) .
C1 N2 C2 C3 -0.9(3) .
C4 N1 C3 C2 0.1(3) .
Co1 N1 C3 C2 178.54(16) .
N2 C2 C3 N1 0.6(4) .
C3 N1 C4 C1 -0.6(3) .
Co1 N1 C4 C1 -179.19(15) .
C3 N1 C4 C5 -178.38(17) .
Co1 N1 C4 C5 3.0(2) .
N2 C1 C4 N1 0.3(3) .
N2 C1 C4 C5 177.82(19) .
N4 N3 C5 N5 -1.1(2) .
Co1 N3 C5 N5 174.45(12) .
N4 N3 C5 C4 178.22(17) .
Co1 N3 C5 C4 -6.2(2) .
C6 N5 C5 N3 0.4(2) .
N6 N5 C5 N3 -179.75(17) .
C6 N5 C5 C4 -178.8(2) .
N6 N5 C5 C4 1.0(3) .
N1 C4 C5 N3 2.1(3) .
C1 C4 C5 N3 -175.6(2) .
N1 C4 C5 N5 -178.74(19) .
C1 C4 C5 N5 3.6(3) .
N3 N4 C6 N5 -1.1(2) .
N3 N4 C6 C7 179.86(18) .
C5 N5 C6 N4 0.5(2) .
N6 N5 C6 N4 -179.36(19) .
C5 N5 C6 C7 179.4(2) .
N6 N5 C6 C7 -0.4(3) .
C10 N7 C7 C8 -0.9(3) .
C10 N7 C7 C6 179.3(2) .
N4 C6 C7 N7 178.9(2) .
N5 C6 C7 N7 0.1(3) .
N4 C6 C7 C8 -0.9(3) .
N5 C6 C7 C8 -179.7(2) .
C9 N8 C8 C7 0.2(3) .
N7 C7 C8 N8 0.8(4) .
C6 C7 C8 N8 -179.4(2) .
C8 N8 C9 C10 -1.0(4) .
C7 N7 C10 C9 0.1(4) .
N8 C9 C10 N7 0.9(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144724
