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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/66/1556626.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_1556626
loop_
_publ_author_name
'Hazra, S.'
'Rocha, B.G.M.'
'Guedes da Silva, M.F.C.'
'Karmakar, A.'
'Pombeiro, A.J.L.'
_publ_section_title
;
 Syntheses, Structures, and Catalytic Hydrocarbon Oxidation Properties of
 N-Heterocycle-Sulfonated Schiff Base Copper(II) Complexes
;
_journal_name_full               Inorganics
_journal_page_first              17
_journal_paper_doi               10.3390/inorganics7020017
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C23 H17 Cu N3 O4 S, C H4 O'
_chemical_formula_sum            'C24 H21 Cu N3 O5 S'
_chemical_formula_weight         527.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90.0000(9)
_cell_angle_beta                 109.3950(9)
_cell_angle_gamma                90.0000(9)
_cell_formula_units_Z            4
_cell_length_a                   8.1099(2)
_cell_length_b                   29.4538(7)
_cell_length_c                   10.5303(3)
_cell_measurement_reflns_used    7150
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.47
_cell_volume                     2372.60(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24195
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.473
_exptl_absorpt_coefficient_mu    1.049
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_correction_T_min  0.8
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       prism
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0595P)²+0.9242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1028
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3903
_reflns_number_total             4826
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Inorganics-2019-7-17.cif
_cod_data_source_block           Compound3
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1556626
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0810(3) 0.15474(8) 0.3851(2) 0.0358(5) Uani 1 1 d . . . . .
C2 C -0.0782(3) 0.16322(9) 0.2868(3) 0.0475(6) Uani 1 1 d . . . . .
H2 H -0.1116 0.1465 0.2074 0.057 Uiso 1 1 calc R U . . .
C3 C -0.1880(4) 0.19656(10) 0.3060(3) 0.0582(8) Uani 1 1 d . . . . .
H3 H -0.2968 0.2013 0.2410 0.070 Uiso 1 1 calc R U . . .
C4 C -0.1366(4) 0.22258(10) 0.4207(4) 0.0609(8) Uani 1 1 d . . . . .
H4 H -0.2086 0.2457 0.4318 0.073 Uiso 1 1 calc R U . . .
C5 C 0.0221(3) 0.21436(9) 0.5198(3) 0.0475(6) Uani 1 1 d . . . . .
H5 H 0.0567 0.2322 0.5971 0.057 Uiso 1 1 calc R U . . .
C6 C 0.1301(3) 0.17981(8) 0.5048(2) 0.0354(5) Uani 1 1 d . . . . .
C7 C 0.4091(3) 0.19837(8) 0.6456(2) 0.0387(5) Uani 1 1 d . . . . .
H7 H 0.3830 0.2262 0.6018 0.046 Uiso 1 1 calc R U . . .
C11 C 0.5798(3) 0.19376(9) 0.7424(2) 0.0393(5) Uani 1 1 d . . . . .
C12 C 0.6940(4) 0.23151(10) 0.7621(3) 0.0530(7) Uani 1 1 d . . . . .
H12 H 0.6548 0.2581 0.7138 0.064 Uiso 1 1 calc R U . . .
C13 C 0.8603(4) 0.22949(12) 0.8505(3) 0.0618(8) Uani 1 1 d . . . . .
H13 H 0.9341 0.2545 0.8622 0.074 Uiso 1 1 calc R U . . .
C14 C 0.9184(4) 0.19028(12) 0.9223(3) 0.0604(8) Uani 1 1 d . . . . .
H14 H 1.0313 0.1893 0.9838 0.073 Uiso 1 1 calc R U . . .
C15 C 0.8136(4) 0.15259(11) 0.9054(3) 0.0536(7) Uani 1 1 d . . . . .
H15 H 0.8571 0.1264 0.9546 0.064 Uiso 1 1 calc R U . . .
C16 C 0.6395(3) 0.15304(9) 0.8137(2) 0.0404(6) Uani 1 1 d . . . . .
C21 C -0.0909(3) 0.11456(9) 0.6194(3) 0.0466(6) Uani 1 1 d . . . . .
H21 H -0.0761 0.1459 0.6228 0.056 Uiso 1 1 calc R U . . .
C22 C -0.2576(4) 0.09771(11) 0.5760(3) 0.0526(7) Uani 1 1 d . . . . .
H22 H -0.3534 0.1171 0.5483 0.063 Uiso 1 1 calc R U . . .
C23 C -0.2804(4) 0.05151(11) 0.5743(3) 0.0595(8) Uani 1 1 d . . . . .
H23 H -0.3921 0.0391 0.5432 0.071 Uiso 1 1 calc R U . . .
C24 C -0.1360(4) 0.02384(10) 0.6189(3) 0.0551(7) Uani 1 1 d . . . . .
H24 H -0.1493 -0.0075 0.6216 0.066 Uiso 1 1 calc R U . . .
C25 C 0.0299(3) 0.04303(8) 0.6601(3) 0.0403(6) Uani 1 1 d . . . . .
C26 C 0.1919(3) 0.01622(9) 0.7122(3) 0.0438(6) Uani 1 1 d . . . . .
C27 C 0.1967(4) -0.03034(10) 0.7272(4) 0.0664(9) Uani 1 1 d . . . . .
H27 H 0.0933 -0.0469 0.7041 0.080 Uiso 1 1 calc R U . . .
C28 C 0.3547(5) -0.05195(12) 0.7762(4) 0.0820(11) Uani 1 1 d . . . . .
H28 H 0.3594 -0.0834 0.7859 0.098 Uiso 1 1 calc R U . . .
C29 C 0.5057(5) -0.02706(12) 0.8110(4) 0.0798(11) Uani 1 1 d . . . . .
H29 H 0.6142 -0.0412 0.8447 0.096 Uiso 1 1 calc R U . . .
C30 C 0.4935(4) 0.01945(10) 0.7947(3) 0.0600(8) Uani 1 1 d . . . . .
H30 H 0.5955 0.0366 0.8193 0.072 Uiso 1 1 calc R U . . .
C40 C 0.3743(6) 0.15248(15) 1.0206(4) 0.0925(14) Uani 1 1 d . . . . .
H40A H 0.3478 0.1662 0.9334 0.139 Uiso 1 1 calc R U . . .
H40B H 0.2925 0.1285 1.0164 0.139 Uiso 1 1 calc R U . . .
H40C H 0.4907 0.1403 1.0483 0.139 Uiso 1 1 calc R U . . .
N1 N 0.2867(2) 0.16814(6) 0.61208(19) 0.0341(4) Uani 1 1 d . . . . .
N2 N 0.0526(3) 0.08821(7) 0.6575(2) 0.0378(5) Uani 1 1 d . . . . .
N3 N 0.3395(3) 0.04064(7) 0.7446(2) 0.0436(5) Uani 1 1 d . . . . .
O1 O 0.5449(2) 0.11630(6) 0.79839(19) 0.0466(4) Uani 1 1 d . . . . .
O11 O 0.2721(3) 0.08251(6) 0.46751(18) 0.0449(4) Uani 1 1 d . . . . .
O12 O 0.1322(3) 0.09290(7) 0.2285(2) 0.0575(5) Uani 1 1 d . . . . .
O13 O 0.3771(2) 0.14035(7) 0.35041(19) 0.0494(5) Uani 1 1 d . . . . .
O40 O 0.3626(3) 0.18508(8) 1.1131(2) 0.0704(6) Uani 1 1 d . . . . .
H40 H 0.3614 0.1725 1.1823 0.106 Uiso 1 1 calc R U . . .
S1 S 0.22733(8) 0.11409(2) 0.35453(6) 0.03739(15) Uani 1 1 d . . . . .
Cu1 Cu 0.30898(4) 0.10637(2) 0.69109(3) 0.03686(11) 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'
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'
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
C2 C1 C6 119.6(2) . .
C2 C1 S1 119.7(2) . .
C6 C1 S1 120.54(18) . .
C1 C2 C3 120.3(3) . .
C4 C3 C2 120.1(3) . .
C3 C4 C5 120.0(3) . .
C4 C5 C6 120.5(3) . .
C5 C6 C1 119.3(2) . .
C5 C6 N1 121.0(2) . .
C1 C6 N1 119.7(2) . .
N1 C7 C11 127.2(2) . .
C16 C11 C12 119.7(2) . .
C16 C11 C7 122.7(2) . .
C12 C11 C7 117.5(2) . .
C13 C12 C11 121.1(3) . .
C12 C13 C14 119.6(3) . .
C15 C14 C13 121.6(3) . .
C14 C15 C16 120.9(3) . .
O1 C16 C11 123.7(2) . .
O1 C16 C15 119.1(2) . .
C11 C16 C15 117.2(2) . .
N2 C21 C22 123.5(3) . .
C21 C22 C23 118.5(3) . .
C24 C23 C22 119.2(3) . .
C23 C24 C25 119.5(3) . .
N2 C25 C24 121.4(2) . .
N2 C25 C26 115.2(2) . .
C24 C25 C26 123.3(2) . .
N3 C26 C27 121.0(3) . .
N3 C26 C25 114.7(2) . .
C27 C26 C25 124.2(3) . .
C28 C27 C26 119.5(3) . .
C29 C28 C27 119.6(3) . .
C28 C29 C30 118.5(3) . .
N3 C30 C29 122.1(3) . .
C7 N1 C6 116.7(2) . .
C7 N1 Cu1 124.25(17) . .
C6 N1 Cu1 118.92(14) . .
C21 N2 C25 117.8(2) . .
C21 N2 Cu1 128.73(18) . .
C25 N2 Cu1 112.99(16) . .
C30 N3 C26 119.2(2) . .
C30 N3 Cu1 124.91(19) . .
C26 N3 Cu1 115.42(17) . .
C16 O1 Cu1 129.61(16) . .
S1 O11 Cu1 122.30(10) . .
O12 S1 O13 113.65(12) . .
O12 S1 O11 112.85(12) . .
O13 S1 O11 112.31(11) . .
O12 S1 C1 105.80(12) . .
O13 S1 C1 105.09(11) . .
O11 S1 C1 106.30(11) . .
O1 Cu1 N1 92.40(8) . .
O1 Cu1 N3 88.58(8) . .
N1 Cu1 N3 170.85(8) . .
O1 Cu1 N2 154.75(8) . .
N1 Cu1 N2 102.71(8) . .
N3 Cu1 N2 79.71(8) . .
O1 Cu1 O11 113.95(8) . .
N1 Cu1 O11 83.79(7) . .
N3 Cu1 O11 87.49(8) . .
N2 Cu1 O11 88.01(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.383(3) .
C1 C6 1.400(3) .
C1 S1 1.788(2) .
C2 C3 1.385(4) .
C3 C4 1.373(4) .
C4 C5 1.383(4) .
C5 C6 1.385(3) .
C6 N1 1.434(3) .
C7 N1 1.292(3) .
C7 C11 1.427(3) .
C11 C16 1.412(4) .
C11 C12 1.418(4) .
C12 C13 1.362(4) .
C13 C14 1.375(5) .
C14 C15 1.373(4) .
C15 C16 1.421(4) .
C16 O1 1.305(3) .
C21 N2 1.345(3) .
C21 C22 1.368(4) .
C22 C23 1.372(4) .
C23 C24 1.375(4) .
C24 C25 1.389(4) .
C25 N2 1.345(3) .
C25 C26 1.474(4) .
C26 N3 1.340(3) .
C26 C27 1.379(4) .
C27 C28 1.369(5) .
C28 C29 1.369(5) .
C29 C30 1.380(4) .
C30 N3 1.337(3) .
C40 O40 1.393(4) .
N1 Cu1 1.9837(19) .
N2 Cu1 2.061(2) .
N3 Cu1 2.009(2) .
O1 Cu1 1.8942(18) .
O11 S1 1.4580(19) .
O11 Cu1 2.3789(18) .
O12 S1 1.438(2) .
O13 S1 1.4524(19) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O40 H40 O13 0.82 1.97 2.792(3) 175.5 1_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305861
