#------------------------------------------------------------------------------
#$Date: 2023-03-06 01:20:04 +0200 (Mon, 06 Mar 2023) $
#$Revision: 281637 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/86/1568600.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_1568600
loop_
_publ_author_name
'Dubskikh, Vadim A.'
'Kolosov, Aleksei A.'
'Lysova, Anna A.'
'Samsonenko, Denis G.'
'Lavrov, Alexander N.'
'Kovalenko, Konstantin A.'
'Dybtsev, Danil N.'
'Fedin, Vladimir P.'
_publ_section_title
;
 A Series of Metal--Organic Frameworks with 2,2′-Bipyridyl
 Derivatives: Synthesis vs. Structure Relationships, Adsorption, and
 Magnetic Studies
;
_journal_issue                   5
_journal_name_full               Molecules
_journal_page_first              2139
_journal_paper_doi               10.3390/molecules28052139
_journal_volume                  28
_journal_year                    2023
_chemical_formula_sum            'C22 H16 Mn N2 O4 S2'
_chemical_formula_weight         491.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                102.277(4)
_cell_angle_beta                 91.709(4)
_cell_angle_gamma                117.108(5)
_cell_formula_units_Z            2
_cell_length_a                   10.5007(5)
_cell_length_b                   10.5738(6)
_cell_length_c                   11.0290(5)
_cell_measurement_reflns_used    4027
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      28.62
_cell_measurement_theta_min      2.51
_cell_volume                     1053.76(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2018 (Sheldrick, 2015)'
_diffrn_ambient_temperature      140(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7812
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.041
_diffrn_reflns_theta_min         2.202
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       plate
_exptl_crystal_F_000             502
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.141
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0412P)²+0.5152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3827
_reflns_number_total             4607
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            3-final.cif
_cod_data_source_block           SSM-6C
_cod_original_cell_volume        1053.76(10)
_cod_database_code               1568600
_shelx_shelxl_version_number     2018/3
_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_min   0.882
_shelx_estimated_absorpt_t_max   0.942
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.46649(4) 0.37100(3) 0.09789(3) 0.01844(10) Uani 1 1 d . . . . .
O11 O 0.61236(18) 0.59613(16) 0.08617(13) 0.0258(4) Uani 1 1 d . . . . .
O12 O 0.68048(19) 0.82276(17) 0.07851(14) 0.0290(4) Uani 1 1 d . . . . .
C11 C 0.6844(2) 0.7337(2) 0.13411(19) 0.0197(5) Uani 1 1 d . . . . .
C12 C 0.7765(2) 0.7864(2) 0.25571(19) 0.0217(5) Uani 1 1 d . . . . .
C13 C 0.7995(3) 0.7070(3) 0.3261(2) 0.0351(6) Uani 1 1 d . . . . .
H13 H 0.753617 0.602704 0.303195 0.042 Uiso 1 1 calc R U . . .
C14 C 0.8973(3) 0.7927(3) 0.4360(2) 0.0373(7) Uani 1 1 d . . . . .
H14 H 0.924612 0.752716 0.495138 0.045 Uiso 1 1 calc R U . . .
C15 C 0.9493(3) 0.9401(2) 0.44939(19) 0.0230(5) Uani 1 1 d . . . . .
S1 S 0.87680(7) 0.97129(6) 0.32387(5) 0.02718(15) Uani 1 1 d . . . . .
O21 O 0.27648(18) 0.38180(18) 0.16671(14) 0.0263(4) Uani 1 1 d . . . . .
O22 O 0.47326(19) 0.48615(19) 0.30583(15) 0.0297(4) Uani 1 1 d . . . . .
C21 C 0.3431(3) 0.4497(2) 0.2764(2) 0.0226(5) Uani 1 1 d . . . . .
C22 C 0.2616(3) 0.4840(2) 0.3734(2) 0.0218(5) Uani 1 1 d . . . . .
C23 C 0.3090(3) 0.5567(3) 0.4970(2) 0.0248(5) Uani 1 1 d . . . . .
H23 H 0.405126 0.594003 0.536531 0.030 Uiso 1 1 calc R U . . .
C24 C 0.1990(3) 0.5702(3) 0.5592(2) 0.0246(5) Uani 1 1 d . . . . .
H24 H 0.213977 0.619004 0.645385 0.029 Uiso 1 1 calc R U . . .
C25 C 0.0684(3) 0.5063(2) 0.48400(19) 0.0216(5) Uani 1 1 d . . . . .
S2 S 0.08153(6) 0.43097(6) 0.33230(5) 0.02278(14) Uani 1 1 d . . . . .
N1 N 0.6445(2) 0.3152(2) 0.05746(16) 0.0221(4) Uani 1 1 d . . . . .
N2 N 0.4362(2) 0.1866(2) 0.19006(16) 0.0229(4) Uani 1 1 d . . . . .
C101 C 0.7442(3) 0.3783(3) -0.0145(2) 0.0275(5) Uani 1 1 d . . . . .
H101 H 0.745397 0.457767 -0.042587 0.033 Uiso 1 1 calc R U . . .
C102 C 0.8445(3) 0.3329(3) -0.0493(2) 0.0302(5) Uani 1 1 d . . . . .
H102 H 0.911677 0.379809 -0.101591 0.036 Uiso 1 1 calc R U . . .
C103 C 0.8480(3) 0.2193(3) -0.0086(2) 0.0294(5) Uani 1 1 d . . . . .
C104 C 0.7441(3) 0.1528(3) 0.0643(2) 0.0268(5) Uani 1 1 d . . . . .
H104 H 0.741208 0.073231 0.093215 0.032 Uiso 1 1 calc R U . . .
C105 C 0.6442(2) 0.2019(2) 0.09532(19) 0.0212(5) Uani 1 1 d . . . . .
C106 C 0.5297(3) 0.1330(2) 0.17278(19) 0.0212(5) Uani 1 1 d . . . . .
C107 C 0.5220(3) 0.0218(3) 0.2253(2) 0.0279(5) Uani 1 1 d . . . . .
H107 H 0.589698 -0.014166 0.211046 0.034 Uiso 1 1 calc R U . . .
C108 C 0.4153(3) -0.0368(3) 0.2985(2) 0.0312(6) Uani 1 1 d . . . . .
C109 C 0.3204(3) 0.0201(3) 0.3161(2) 0.0358(6) Uani 1 1 d . . . . .
H109 H 0.246328 -0.015902 0.366364 0.043 Uiso 1 1 calc R U . . .
C110 C 0.3339(3) 0.1297(3) 0.2602(2) 0.0308(6) Uani 1 1 d . . . . .
H110 H 0.266677 0.166500 0.272343 0.037 Uiso 1 1 calc R U . . .
C111 C 0.9587(3) 0.1699(3) -0.0397(3) 0.0424(7) Uani 1 1 d . . . . .
H11A H 0.920531 0.067122 -0.036899 0.064 Uiso 1 1 calc R U . . .
H11B H 1.046814 0.231273 0.021325 0.064 Uiso 1 1 calc R U . . .
H11C H 0.981262 0.178909 -0.124071 0.064 Uiso 1 1 calc R U . . .
C112 C 0.4036(4) -0.1587(3) 0.3547(3) 0.0446(7) Uani 1 1 d . . . . .
H11D H 0.350354 -0.160839 0.426384 0.067 Uiso 1 1 calc R U . . .
H11E H 0.500764 -0.141823 0.382955 0.067 Uiso 1 1 calc R U . . .
H11F H 0.352222 -0.252795 0.291563 0.067 Uiso 1 1 calc R U . . .
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
_geom_angle_publ_flag
O11 Mn1 O11 71.72(6) . 2_665 ?
O11 Mn1 O12 55.62(5) 2_665 2_665 ?
O11 Mn1 O12 123.45(5) . 2_665 ?
O11 Mn1 O22 83.85(6) . . ?
O11 Mn1 O22 129.12(6) 2_665 . ?
O11 Mn1 C21 95.07(6) . . ?
O11 Mn1 C21 108.77(6) 2_665 . ?
O11 Mn1 N1 88.41(7) . . ?
O11 Mn1 N2 145.87(7) . . ?
O12 Mn1 C21 118.72(7) 2_665 . ?
O21 Mn1 O11 85.49(6) . 2_665 ?
O21 Mn1 O11 104.62(6) . . ?
O21 Mn1 O12 91.29(6) . 2_665 ?
O21 Mn1 O22 58.01(6) . . ?
O21 Mn1 C21 29.16(7) . . ?
O21 Mn1 N1 164.63(6) . . ?
O21 Mn1 N2 92.45(6) . . ?
O22 Mn1 O12 144.88(6) . 2_665 ?
O22 Mn1 C21 28.86(7) . . ?
N1 Mn1 O11 106.67(6) . 2_665 ?
N1 Mn1 O12 88.14(6) . 2_665 ?
N1 Mn1 O22 116.74(6) . . ?
N1 Mn1 C21 143.65(7) . . ?
N1 Mn1 N2 72.21(7) . . ?
N2 Mn1 O11 140.09(6) . 2_665 ?
N2 Mn1 O12 84.65(6) . 2_665 ?
N2 Mn1 O22 80.52(6) . . ?
N2 Mn1 C21 85.59(7) . . ?
Mn1 O11 Mn1 108.28(6) . 2_665 ?
C11 O11 Mn1 92.29(12) . 2_665 ?
C11 O11 Mn1 151.92(14) . . ?
C11 O12 Mn1 90.83(13) . 2_665 ?
O11 C11 C12 118.67(19) . . ?
O12 C11 O11 121.10(19) . . ?
O12 C11 C12 120.2(2) . . ?
C11 C12 S1 120.39(16) . . ?
C13 C12 C11 128.5(2) . . ?
C13 C12 S1 111.13(18) . . ?
C12 C13 H13 123.2 . . ?
C12 C13 C14 113.7(2) . . ?
C14 C13 H13 123.2 . . ?
C13 C14 H14 123.6 . . ?
C15 C14 C13 112.8(2) . . ?
C15 C14 H14 123.6 . . ?
C14 C15 C15 128.1(3) . 2_776 ?
C14 C15 S1 110.56(17) . . ?
C15 C15 S1 121.4(2) 2_776 . ?
C12 S1 C15 91.81(11) . . ?
C21 O21 Mn1 92.71(14) . . ?
C21 O22 Mn1 86.57(13) . . ?
O21 C21 Mn1 58.14(11) . . ?
O21 C21 C22 117.9(2) . . ?
O22 C21 Mn1 64.58(12) . . ?
O22 C21 O21 122.7(2) . . ?
O22 C21 C22 119.4(2) . . ?
C22 C21 Mn1 175.40(18) . . ?
C21 C22 S2 119.00(17) . . ?
C23 C22 C21 129.0(2) . . ?
C23 C22 S2 111.97(17) . . ?
C22 C23 H23 123.9 . . ?
C22 C23 C24 112.2(2) . . ?
C24 C23 H23 123.9 . . ?
C23 C24 H24 123.1 . . ?
C25 C24 C23 113.7(2) . . ?
C25 C24 H24 123.1 . . ?
C24 C25 C25 129.2(2) . 2_566 ?
C24 C25 S2 110.65(17) . . ?
C25 C25 S2 120.2(2) 2_566 . ?
C22 S2 C25 91.44(11) . . ?
C101 N1 Mn1 123.33(15) . . ?
C101 N1 C105 117.5(2) . . ?
C105 N1 Mn1 118.78(15) . . ?
C106 N2 Mn1 117.20(14) . . ?
C110 N2 Mn1 125.08(16) . . ?
C110 N2 C106 117.72(19) . . ?
N1 C101 H101 118.6 . . ?
N1 C101 C102 122.9(2) . . ?
C102 C101 H101 118.6 . . ?
C101 C102 H102 119.8 . . ?
C101 C102 C103 120.3(2) . . ?
C103 C102 H102 119.8 . . ?
C102 C103 C104 116.8(2) . . ?
C102 C103 C111 122.3(2) . . ?
C104 C103 C111 120.9(2) . . ?
C103 C104 H104 119.8 . . ?
C103 C104 C105 120.5(2) . . ?
C105 C104 H104 119.8 . . ?
N1 C105 C104 122.0(2) . . ?
N1 C105 C106 115.68(19) . . ?
C104 C105 C106 122.3(2) . . ?
N2 C106 C105 115.89(18) . . ?
N2 C106 C107 122.0(2) . . ?
C107 C106 C105 122.1(2) . . ?
C106 C107 H107 120.0 . . ?
C108 C107 C106 120.0(2) . . ?
C108 C107 H107 120.0 . . ?
C107 C108 C112 120.9(2) . . ?
C109 C108 C107 117.3(2) . . ?
C109 C108 C112 121.7(2) . . ?
C108 C109 H109 120.3 . . ?
C108 C109 C110 119.4(2) . . ?
C110 C109 H109 120.3 . . ?
N2 C110 C109 123.5(2) . . ?
N2 C110 H110 118.3 . . ?
C109 C110 H110 118.3 . . ?
C103 C111 H11A 109.5 . . ?
C103 C111 H11B 109.5 . . ?
C103 C111 H11C 109.5 . . ?
H11A C111 H11B 109.5 . . ?
H11A C111 H11C 109.5 . . ?
H11B C111 H11C 109.5 . . ?
C108 C112 H11D 109.5 . . ?
C108 C112 H11E 109.5 . . ?
C108 C112 H11F 109.5 . . ?
H11D C112 H11E 109.5 . . ?
H11D C112 H11F 109.5 . . ?
H11E C112 H11F 109.5 . . ?
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
Mn1 O11 2.2021(16) . yes
Mn1 O11 2.3214(15) 2_665 yes
Mn1 O12 2.3682(16) 2_665 yes
Mn1 O21 2.1980(16) . yes
Mn1 O22 2.3390(16) . yes
Mn1 C21 2.585(2) . yes
Mn1 N1 2.2331(19) . yes
Mn1 N2 2.2881(18) . yes
O11 C11 1.270(3) . ?
O12 C11 1.243(3) . ?
C11 C12 1.469(3) . ?
C12 C13 1.347(3) . ?
C12 S1 1.717(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.368(3) . ?
C15 C15 1.444(4) 2_776 ?
C15 S1 1.722(2) . ?
O21 C21 1.261(3) . ?
O22 C21 1.250(3) . ?
C21 C22 1.477(3) . ?
C22 C23 1.365(3) . ?
C22 S2 1.724(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.407(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.369(3) . ?
C25 C25 1.443(5) 2_566 ?
C25 S2 1.732(2) . ?
N1 C101 1.346(3) . ?
N1 C105 1.348(3) . ?
N2 C106 1.339(3) . ?
N2 C110 1.331(3) . ?
C101 H101 0.9500 . ?
C101 C102 1.376(3) . ?
C102 H102 0.9500 . ?
C102 C103 1.385(3) . ?
C103 C104 1.387(3) . ?
C103 C111 1.498(3) . ?
C104 H104 0.9500 . ?
C104 C105 1.388(3) . ?
C105 C106 1.495(3) . ?
C106 C107 1.390(3) . ?
C107 H107 0.9500 . ?
C107 C108 1.387(3) . ?
C108 C109 1.379(4) . ?
C108 C112 1.503(3) . ?
C109 H109 0.9500 . ?
C109 C110 1.380(3) . ?
C110 H110 0.9500 . ?
C111 H11A 0.9800 . ?
C111 H11B 0.9800 . ?
C111 H11C 0.9800 . ?
C112 H11D 0.9800 . ?
C112 H11E 0.9800 . ?
C112 H11F 0.9800 . ?
