#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/16/4501660.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_4501660
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            'C24 H24 Mn2 N20 O4 S4'
_chemical_formula_weight         894.75
_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                89.581(2)
_cell_angle_beta                 76.333(2)
_cell_angle_gamma                84.805(2)
_cell_formula_units_Z            1
_cell_length_a                   8.2830(13)
_cell_length_b                   9.5447(14)
_cell_length_c                   11.7786(18)
_cell_measurement_reflns_used    2031
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.17
_cell_volume                     901.0(2)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4950
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.997
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.615591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0287
_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)+(0.0461P)²+0.0660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                2638
_reflns_number_total             3139
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100200b_si_002.cif
_cod_data_source_block           8
_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 2.4.2 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_sg_symbol_H-M      P-1
_cod_database_code               4501660
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
Mn1 Mn 0.75438(4) 0.78585(3) 0.80185(2) 0.03304(12) Uani 1 1 d .
O1 O 0.5078(2) 0.72834(18) 0.90297(13) 0.0560(5) Uani 1 1 d D
H1B H 0.4356 0.6989 0.8705 0.084 Uiso 1 1 d RD
H1A H 0.5032 0.7012 0.9725 0.084 Uiso 1 1 d RD
S1 S 0.53945(8) 1.27944(6) 0.80926(5) 0.04619(17) Uani 1 1 d .
S2 S 1.24623(8) 0.93052(7) 0.52984(5) 0.05208(18) Uani 1 1 d .
N1 N 0.7061(2) 0.67447(17) 0.63807(14) 0.0337(4) Uani 1 1 d .
N2 N 0.7000(3) 0.5421(2) 0.42977(15) 0.0455(5) Uani 1 1 d .
N3 N 0.8462(2) 0.55408(17) 0.79952(15) 0.0385(4) Uani 1 1 d .
N4 N 0.9221(2) 0.47165(18) 0.87056(15) 0.0423(5) Uani 1 1 d .
N5 N 0.9355(2) 0.35312(16) 0.70978(13) 0.0293(4) Uani 1 1 d .
N6 N 0.9725(2) 0.24964(18) 0.61979(14) 0.0395(4) Uani 1 1 d .
H6A H 0.8800 0.2091 0.6193 0.047 Uiso 1 1 d R
H6B H 1.0500 0.1851 0.6333 0.047 Uiso 1 1 d R
N7 N 1.1814(2) 0.16164(17) 1.02409(14) 0.0337(4) Uani 1 1 d .
N8 N 1.1221(2) 0.11964(18) 0.80377(15) 0.0431(5) Uani 1 1 d .
N9 N 0.6441(3) 0.9932(2) 0.78441(17) 0.0551(5) Uani 1 1 d .
N10 N 0.9987(3) 0.8233(2) 0.69989(17) 0.0500(5) Uani 1 1 d .
C1 C 0.7786(3) 0.5427(2) 0.61115(16) 0.0316(4) Uani 1 1 d .
C2 C 0.6293(3) 0.7367(2) 0.56160(18) 0.0406(5) Uani 1 1 d .
H2 H 0.5759 0.8267 0.5780 0.049 Uiso 1 1 calc R
C3 C 0.6271(3) 0.6701(2) 0.45747(19) 0.0448(6) Uani 1 1 d .
H3 H 0.5726 0.7171 0.4058 0.054 Uiso 1 1 calc R
C4 C 0.7753(3) 0.4780(2) 0.50747(18) 0.0396(5) Uani 1 1 d .
H4 H 0.8267 0.3873 0.4911 0.048 Uiso 1 1 calc R
C5 C 0.8549(2) 0.48191(19) 0.70326(16) 0.0304(4) Uani 1 1 d .
C6 C 0.9749(3) 0.3501(2) 0.81559(17) 0.0329(5) Uani 1 1 d .
C7 C 1.0655(3) 0.2374(2) 0.86571(17) 0.0321(5) Uani 1 1 d .
C8 C 1.2065(3) 0.0226(2) 0.8545(2) 0.0480(6) Uani 1 1 d .
H8 H 1.2465 -0.0623 0.8151 0.058 Uiso 1 1 calc R
C9 C 1.2368(3) 0.0429(2) 0.96239(18) 0.0384(5) Uani 1 1 d .
H9 H 1.2974 -0.0278 0.9935 0.046 Uiso 1 1 calc R
C10 C 1.0947(3) 0.2583(2) 0.97452(17) 0.0375(5) Uani 1 1 d .
H10 H 1.0526 0.3424 1.0146 0.045 Uiso 1 1 calc R
C11 C 0.6009(3) 1.1120(2) 0.79434(17) 0.0393(5) Uani 1 1 d .
C12 C 1.1010(3) 0.8688(2) 0.62911(18) 0.0364(5) Uani 1 1 d .
O2 O 0.2921(3) 0.6180(2) 0.7904(2) 0.0914(7) Uani 1 1 d D
H2A H 0.3022 0.5707 0.7279 0.137 Uiso 1 1 d RD
H2B H 0.2842 0.5723 0.8533 0.137 Uiso 1 1 d RD
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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 Mn1 N10 95.24(8) . .
N9 Mn1 O1 89.10(8) . .
N10 Mn1 O1 175.21(7) . .
N9 Mn1 N3 170.36(7) . .
N10 Mn1 N3 87.75(8) . .
O1 Mn1 N3 87.65(7) . .
N9 Mn1 N7 93.50(7) . 2_767
N10 Mn1 N7 93.10(7) . 2_767
O1 Mn1 N7 88.67(6) . 2_767
N3 Mn1 N7 95.49(6) . 2_767
N9 Mn1 N1 100.57(7) . .
N10 Mn1 N1 88.69(7) . .
O1 Mn1 N1 88.50(6) . .
N3 Mn1 N1 70.28(6) . .
N7 Mn1 N1 165.60(6) 2_767 .
Mn1 O1 H1B 122.6 . .
Mn1 O1 H1A 116.2 . .
H1B O1 H1A 115.9 . .
C2 N1 C1 116.93(17) . .
C2 N1 Mn1 124.80(14) . .
C1 N1 Mn1 117.76(12) . .
C3 N2 C4 116.89(18) . .
C5 N3 N4 108.10(16) . .
C5 N3 Mn1 117.13(13) . .
N4 N3 Mn1 133.85(12) . .
C6 N4 N3 107.28(16) . .
C5 N5 C6 105.79(15) . .
C5 N5 N6 124.69(15) . .
C6 N5 N6 129.48(16) . .
N5 N6 H6A 108.8 . .
N5 N6 H6B 109.3 . .
H6A N6 H6B 109.5 . .
C10 N7 C9 115.92(17) . .
C10 N7 Mn1 119.50(13) . 2_767
C9 N7 Mn1 124.35(13) . 2_767
C7 N8 C8 115.66(17) . .
C11 N9 Mn1 164.97(19) . .
C12 N10 Mn1 159.9(2) . .
N1 C1 C4 120.98(18) . .
N1 C1 C5 112.52(16) . .
C4 C1 C5 126.49(19) . .
N1 C2 C3 121.4(2) . .
N1 C2 H2 119.3 . .
C3 C2 H2 119.3 . .
N2 C3 C2 122.0(2) . .
N2 C3 H3 119.0 . .
C2 C3 H3 119.0 . .
N2 C4 C1 121.8(2) . .
N2 C4 H4 119.1 . .
C1 C4 H4 119.1 . .
N3 C5 N5 109.35(16) . .
N3 C5 C1 120.43(17) . .
N5 C5 C1 130.19(17) . .
N4 C6 N5 109.47(17) . .
N4 C6 C7 121.99(17) . .
N5 C6 C7 128.50(18) . .
N8 C7 C10 122.09(18) . .
N8 C7 C6 119.17(17) . .
C10 C7 C6 118.70(18) . .
N8 C8 C9 122.57(19) . .
N8 C8 H8 118.7 . .
C9 C8 H8 118.7 . .
N7 C9 C8 121.78(19) . .
N7 C9 H9 119.1 . .
C8 C9 H9 119.1 . .
N7 C10 C7 121.97(18) . .
N7 C10 H10 119.0 . .
C7 C10 H10 119.0 . .
N9 C11 S1 179.6(2) . .
N10 C12 S2 179.2(2) . .
H2A O2 H2B 117.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 N9 2.133(2) .
Mn1 N10 2.154(2) .
Mn1 O1 2.2216(17) .
Mn1 N3 2.2714(17) .
Mn1 N7 2.3056(16) 2_767
Mn1 N1 2.3416(16) .
O1 H1B 0.8500 .
O1 H1A 0.8501 .
S1 C11 1.630(2) .
S2 C12 1.617(2) .
N1 C2 1.327(3) .
N1 C1 1.350(3) .
N2 C3 1.320(3) .
N2 C4 1.339(3) .
N3 C5 1.315(2) .
N3 N4 1.365(2) .
N4 C6 1.320(3) .
N5 C5 1.355(2) .
N5 C6 1.360(2) .
N5 N6 1.414(2) .
N6 H6A 0.8900 .
N6 H6B 0.8900 .
N7 C10 1.334(3) .
N7 C9 1.335(3) .
N7 Mn1 2.3056(16) 2_767
N8 C7 1.330(2) .
N8 C8 1.333(3) .
N9 C11 1.156(3) .
N10 C12 1.153(3) .
C1 C4 1.380(3) .
C1 C5 1.470(3) .
C2 C3 1.390(3) .
C2 H2 0.9300 .
C3 H3 0.9300 .
C4 H4 0.9300 .
C6 C7 1.457(3) .
C7 C10 1.378(3) .
C8 C9 1.370(3) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 H10 0.9300 .
O2 H2A 0.8500 .
O2 H2B 0.8499 .
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 Mn1 N1 C2 0.22(19) .
N10 Mn1 N1 C2 -94.86(18) .
O1 Mn1 N1 C2 89.02(18) .
N3 Mn1 N1 C2 177.06(19) .
N7 Mn1 N1 C2 167.8(2) 2_767
N9 Mn1 N1 C1 171.74(15) .
N10 Mn1 N1 C1 76.65(15) .
O1 Mn1 N1 C1 -99.46(15) .
N3 Mn1 N1 C1 -11.43(14) .
N7 Mn1 N1 C1 -20.7(3) 2_767
N10 Mn1 N3 C5 -77.92(16) .
O1 Mn1 N3 C5 100.74(16) .
N7 Mn1 N3 C5 -170.82(16) 2_767
N1 Mn1 N3 C5 11.50(15) .
N10 Mn1 N3 N4 89.6(2) .
O1 Mn1 N3 N4 -91.7(2) .
N7 Mn1 N3 N4 -3.3(2) 2_767
N1 Mn1 N3 N4 179.1(2) .
C5 N3 N4 C6 -0.3(2) .
Mn1 N3 N4 C6 -168.67(16) .
N10 Mn1 N9 C11 -80.7(8) .
O1 Mn1 N9 C11 101.4(8) .
N7 Mn1 N9 C11 12.8(8) 2_767
N1 Mn1 N9 C11 -170.3(8) .
N9 Mn1 N10 C12 -32.4(5) .
N3 Mn1 N10 C12 138.5(5) .
N7 Mn1 N10 C12 -126.2(5) 2_767
N1 Mn1 N10 C12 68.1(5) .
C2 N1 C1 C4 1.3(3) .
Mn1 N1 C1 C4 -170.87(16) .
C2 N1 C1 C5 -178.05(18) .
Mn1 N1 C1 C5 9.8(2) .
C1 N1 C2 C3 -1.4(3) .
Mn1 N1 C2 C3 170.23(16) .
C4 N2 C3 C2 0.8(3) .
N1 C2 C3 N2 0.3(4) .
C3 N2 C4 C1 -0.8(3) .
N1 C1 C4 N2 -0.3(3) .
C5 C1 C4 N2 179.0(2) .
N4 N3 C5 N5 0.0(2) .
Mn1 N3 C5 N5 170.56(13) .
N4 N3 C5 C1 178.19(17) .
Mn1 N3 C5 C1 -11.2(3) .
C6 N5 C5 N3 0.4(2) .
N6 N5 C5 N3 -177.62(17) .
C6 N5 C5 C1 -177.6(2) .
N6 N5 C5 C1 4.4(3) .
N1 C1 C5 N3 0.8(3) .
C4 C1 C5 N3 -178.5(2) .
N1 C1 C5 N5 178.60(19) .
C4 C1 C5 N5 -0.7(4) .
N3 N4 C6 N5 0.5(2) .
N3 N4 C6 C7 178.65(19) .
C5 N5 C6 N4 -0.5(2) .
N6 N5 C6 N4 177.29(18) .
C5 N5 C6 C7 -178.5(2) .
N6 N5 C6 C7 -0.7(4) .
C8 N8 C7 C10 1.0(3) .
C8 N8 C7 C6 178.7(2) .
N4 C6 C7 N8 -176.9(2) .
N5 C6 C7 N8 0.8(3) .
N4 C6 C7 C10 0.9(3) .
N5 C6 C7 C10 178.6(2) .
C7 N8 C8 C9 -1.3(4) .
C10 N7 C9 C8 0.3(3) .
Mn1 N7 C9 C8 -174.20(17) 2_767
N8 C8 C9 N7 0.7(4) .
C9 N7 C10 C7 -0.7(3) .
Mn1 N7 C10 C7 174.15(16) 2_767
N8 C7 C10 N7 0.0(3) .
C6 C7 C10 N7 -177.76(19) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168345021
