#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/66/1556625.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_1556625
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         'C20 H20 Cu N2 O5 S'
_chemical_formula_sum            'C20 H20 Cu N2 O5 S'
_chemical_formula_weight         463.98
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 91.883(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5036(4)
_cell_length_b                   18.3619(8)
_cell_length_c                   11.3390(5)
_cell_measurement_reflns_used    3407
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.65
_cell_measurement_theta_min      2.22
_cell_volume                     1977.63(15)
_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      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0555
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14180
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.357
_diffrn_reflns_theta_min         2.112
_exptl_absorpt_coefficient_mu    1.245
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       plate
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0373
_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)+(0.0285P)²+1.8777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2759
_reflns_number_total             3629
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Inorganics-2019-7-17.cif
_cod_data_source_block           Compound2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1556625
_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 0.5699(3) 0.31606(16) 0.3365(3) 0.0173(7) Uani 1 1 d . . . . .
C2 C 0.6257(4) 0.38205(18) 0.3033(3) 0.0270(8) Uani 1 1 d . . . . .
H2 H 0.6151 0.3981 0.2239 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6971(4) 0.4249(2) 0.3860(3) 0.0399(11) Uani 1 1 d . . . . .
H3 H 0.7357 0.4703 0.3634 0.048 Uiso 1 1 calc R U . . .
C4 C 0.7120(4) 0.4015(2) 0.5009(3) 0.0392(11) Uani 1 1 d . . . . .
H4 H 0.7607 0.4311 0.5575 0.047 Uiso 1 1 calc R U . . .
C5 C 0.6570(4) 0.33530(19) 0.5349(3) 0.0278(8) Uani 1 1 d . . . . .
H5 H 0.6674 0.3199 0.6148 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5868(3) 0.29131(16) 0.4530(3) 0.0179(7) Uani 1 1 d . . . . .
C7 C 0.6156(3) 0.18090(16) 0.5497(3) 0.0161(7) Uani 1 1 d . . . . .
H7 H 0.7093 0.1978 0.5628 0.019 Uiso 1 1 calc R U . . .
C11 C 0.5811(3) 0.11236(16) 0.6004(3) 0.0160(7) Uani 1 1 d . . . . .
C12 C 0.6933(3) 0.07050(17) 0.6505(3) 0.0206(7) Uani 1 1 d . . . . .
H12 H 0.7863 0.0895 0.6507 0.025 Uiso 1 1 calc R U . . .
C13 C 0.6708(4) 0.00352(18) 0.6984(3) 0.0248(8) Uani 1 1 d . . . . .
H13 H 0.7470 -0.0238 0.7319 0.030 Uiso 1 1 calc R U . . .
C14 C 0.5337(4) -0.02431(17) 0.6976(3) 0.0243(8) Uani 1 1 d . . . . .
H14 H 0.5172 -0.0712 0.7297 0.029 Uiso 1 1 calc R U . . .
C15 C 0.4230(4) 0.01521(17) 0.6512(3) 0.0228(8) Uani 1 1 d . . . . .
H15 H 0.3309 -0.0048 0.6528 0.027 Uiso 1 1 calc R U . . .
C16 C 0.4418(3) 0.08462(16) 0.6012(3) 0.0167(7) Uani 1 1 d . . . . .
C21 C 0.2521(4) 0.37575(17) 0.4830(3) 0.0335(9) Uani 1 1 d . . . . .
H21A H 0.2917 0.3774 0.4034 0.040 Uiso 1 1 calc R U . . .
H21B H 0.3136 0.4053 0.5365 0.040 Uiso 1 1 calc R U . . .
C22 C 0.1065(4) 0.4088(2) 0.4777(4) 0.0452(11) Uani 1 1 d . . . . .
H22A H 0.1112 0.4582 0.4454 0.068 Uiso 1 1 calc R U . . .
H22B H 0.0695 0.4107 0.5573 0.068 Uiso 1 1 calc R U . . .
H22C H 0.0442 0.3789 0.4270 0.068 Uiso 1 1 calc R U . . .
C23 C 0.0771(3) 0.10608(17) 0.4198(3) 0.0195(7) Uani 1 1 d . . . . .
H23 H 0.1333 0.0706 0.4601 0.023 Uiso 1 1 calc R U . . .
C24 C -0.0596(4) 0.08864(18) 0.3876(3) 0.0282(8) Uani 1 1 d . . . . .
H24 H -0.0963 0.0419 0.4048 0.034 Uiso 1 1 calc R U . . .
C25 C -0.1427(4) 0.13997(18) 0.3299(3) 0.0265(8) Uani 1 1 d . . . . .
H25 H -0.2376 0.1293 0.3072 0.032 Uiso 1 1 calc R U . . .
C26 C -0.0852(3) 0.20698(18) 0.3059(3) 0.0245(8) Uani 1 1 d . . . . .
H26 H -0.1399 0.2433 0.2663 0.029 Uiso 1 1 calc R U . . .
C27 C 0.0526(3) 0.22060(17) 0.3402(3) 0.0203(7) Uani 1 1 d . . . . .
H27 H 0.0917 0.2669 0.3235 0.024 Uiso 1 1 calc R U . . .
N1 N 0.5309(3) 0.22254(13) 0.4873(2) 0.0147(6) Uani 1 1 d . . . . .
N2 N 0.1341(3) 0.17079(13) 0.3966(2) 0.0168(6) Uani 1 1 d . . . . .
O1 O 0.3321(2) 0.12051(11) 0.55926(19) 0.0218(5) Uani 1 1 d . . . . .
O11 O 0.3473(2) 0.24148(12) 0.28416(18) 0.0191(5) Uani 1 1 d . . . . .
O12 O 0.5693(2) 0.19778(11) 0.21278(18) 0.0187(5) Uani 1 1 d . . . . .
O13 O 0.4581(2) 0.30506(11) 0.12599(18) 0.0210(5) Uani 1 1 d . . . . .
O20 O 0.2523(2) 0.30236(12) 0.5234(2) 0.0220(5) Uani 1 1 d . . . . .
S1 S 0.48156(8) 0.26115(4) 0.22954(7) 0.01493(18) Uani 1 1 d . . . . .
Cu1 Cu 0.33405(4) 0.19611(2) 0.44516(3) 0.01533(12) Uani 1 1 d . . . . .
H20O H 0.199(4) 0.2971(18) 0.576(3) 0.023 Uiso 1 1 d . 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'
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 120.6(3) . .
C2 C1 S1 119.5(2) . .
C6 C1 S1 119.9(2) . .
C1 C2 C3 119.9(3) . .
C1 C2 H2 120.0 . .
C3 C2 H2 120.0 . .
C4 C3 C2 119.8(3) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C3 C4 C5 120.7(3) . .
C3 C4 H4 119.6 . .
C5 C4 H4 119.6 . .
C4 C5 C6 120.2(3) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C5 C6 C1 118.7(3) . .
C5 C6 N1 120.5(3) . .
C1 C6 N1 120.7(3) . .
N1 C7 C11 126.2(3) . .
N1 C7 H7 116.9 . .
C11 C7 H7 116.9 . .
C12 C11 C16 119.5(3) . .
C12 C11 C7 117.4(3) . .
C16 C11 C7 123.1(3) . .
C13 C12 C11 121.5(3) . .
C13 C12 H12 119.3 . .
C11 C12 H12 119.3 . .
C12 C13 C14 119.0(3) . .
C12 C13 H13 120.5 . .
C14 C13 H13 120.5 . .
C15 C14 C13 120.8(3) . .
C15 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
C14 C15 C16 121.9(3) . .
C14 C15 H15 119.0 . .
C16 C15 H15 119.0 . .
O1 C16 C15 119.5(3) . .
O1 C16 C11 123.3(3) . .
C15 C16 C11 117.3(3) . .
O20 C21 C22 112.6(3) . .
O20 C21 H21A 109.1 . .
C22 C21 H21A 109.1 . .
O20 C21 H21B 109.1 . .
C22 C21 H21B 109.1 . .
H21A C21 H21B 107.8 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
N2 C23 C24 122.7(3) . .
N2 C23 H23 118.6 . .
C24 C23 H23 118.6 . .
C23 C24 C25 119.2(3) . .
C23 C24 H24 120.4 . .
C25 C24 H24 120.4 . .
C26 C25 C24 118.6(3) . .
C26 C25 H25 120.7 . .
C24 C25 H25 120.7 . .
C27 C26 C25 119.1(3) . .
C27 C26 H26 120.4 . .
C25 C26 H26 120.4 . .
N2 C27 C26 122.5(3) . .
N2 C27 H27 118.7 . .
C26 C27 H27 118.7 . .
C7 N1 C6 116.0(3) . .
C7 N1 Cu1 123.4(2) . .
C6 N1 Cu1 120.58(19) . .
C23 N2 C27 117.9(3) . .
C23 N2 Cu1 122.4(2) . .
C27 N2 Cu1 119.7(2) . .
C16 O1 Cu1 126.2(2) . .
S1 O11 Cu1 124.04(12) . .
C21 O20 Cu1 132.8(2) . .
C21 O20 H20O 111(2) . .
Cu1 O20 H20O 115(2) . .
O13 S1 O12 114.74(13) . .
O13 S1 O11 111.48(13) . .
O12 S1 O11 111.52(13) . .
O13 S1 C1 107.35(14) . .
O12 S1 C1 106.61(13) . .
O11 S1 C1 104.39(14) . .
O1 Cu1 N1 92.58(9) . .
O1 Cu1 O11 157.30(9) . .
N1 Cu1 O11 91.77(9) . .
O1 Cu1 N2 89.29(10) . .
N1 Cu1 N2 177.98(10) . .
O11 Cu1 N2 86.21(9) . .
O1 Cu1 O20 110.37(9) . .
N1 Cu1 O20 91.59(9) . .
O11 Cu1 O20 91.76(8) . .
N2 Cu1 O20 88.48(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.380(4) .
C1 C6 1.401(4) .
C1 S1 1.768(3) .
C2 C3 1.384(5) .
C2 H2 0.9500 .
C3 C4 1.375(5) .
C3 H3 0.9500 .
C4 C5 1.383(5) .
C4 H4 0.9500 .
C5 C6 1.386(4) .
C5 H5 0.9500 .
C6 N1 1.429(4) .
C7 N1 1.303(4) .
C7 C11 1.426(4) .
C7 H7 0.9500 .
C11 C12 1.418(4) .
C11 C16 1.419(4) .
C12 C13 1.364(4) .
C12 H12 0.9500 .
C13 C14 1.399(5) .
C13 H13 0.9500 .
C14 C15 1.369(5) .
C14 H14 0.9500 .
C15 C16 1.409(4) .
C15 H15 0.9500 .
C16 O1 1.309(4) .
C21 O20 1.423(4) .
C21 C22 1.510(5) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 N2 1.335(4) .
C23 C24 1.376(4) .
C23 H23 0.9500 .
C24 C25 1.381(5) .
C24 H24 0.9500 .
C25 C26 1.377(5) .
C25 H25 0.9500 .
C26 C27 1.377(4) .
C26 H26 0.9500 .
C27 N2 1.346(4) .
C27 H27 0.9500 .
N1 Cu1 1.976(2) .
N2 Cu1 2.015(3) .
O1 Cu1 1.898(2) .
O11 S1 1.481(2) .
O11 Cu1 2.014(2) .
O12 S1 1.448(2) .
O13 S1 1.436(2) .
O20 Cu1 2.290(2) .
O20 H20O 0.80(3) .
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -1.0(5) . . . .
S1 C1 C2 C3 -178.9(3) . . . .
C1 C2 C3 C4 -0.1(6) . . . .
C2 C3 C4 C5 0.3(7) . . . .
C3 C4 C5 C6 0.5(6) . . . .
C4 C5 C6 C1 -1.5(5) . . . .
C4 C5 C6 N1 179.4(3) . . . .
C2 C1 C6 C5 1.8(5) . . . .
S1 C1 C6 C5 179.7(3) . . . .
C2 C1 C6 N1 -179.1(3) . . . .
S1 C1 C6 N1 -1.2(4) . . . .
N1 C7 C11 C12 170.9(3) . . . .
N1 C7 C11 C16 -8.3(5) . . . .
C16 C11 C12 C13 0.8(5) . . . .
C7 C11 C12 C13 -178.4(3) . . . .
C11 C12 C13 C14 0.2(5) . . . .
C12 C13 C14 C15 -1.0(5) . . . .
C13 C14 C15 C16 0.8(5) . . . .
C14 C15 C16 O1 -179.2(3) . . . .
C14 C15 C16 C11 0.2(5) . . . .
C12 C11 C16 O1 178.4(3) . . . .
C7 C11 C16 O1 -2.4(5) . . . .
C12 C11 C16 C15 -1.0(4) . . . .
C7 C11 C16 C15 178.2(3) . . . .
N2 C23 C24 C25 -0.7(5) . . . .
C23 C24 C25 C26 0.4(5) . . . .
C24 C25 C26 C27 -0.1(5) . . . .
C25 C26 C27 N2 0.0(5) . . . .
C11 C7 N1 C6 175.6(3) . . . .
C11 C7 N1 Cu1 -2.2(4) . . . .
C5 C6 N1 C7 -47.8(4) . . . .
C1 C6 N1 C7 133.1(3) . . . .
C5 C6 N1 Cu1 130.2(3) . . . .
C1 C6 N1 Cu1 -48.9(4) . . . .
C24 C23 N2 C27 0.6(5) . . . .
C24 C23 N2 Cu1 179.5(3) . . . .
C26 C27 N2 C23 -0.3(5) . . . .
C26 C27 N2 Cu1 -179.2(2) . . . .
C15 C16 O1 Cu1 -157.6(2) . . . .
C11 C16 O1 Cu1 23.0(4) . . . .
C22 C21 O20 Cu1 124.9(3) . . . .
Cu1 O11 S1 O13 -168.62(14) . . . .
Cu1 O11 S1 O12 61.69(18) . . . .
Cu1 O11 S1 C1 -53.03(18) . . . .
C2 C1 S1 O13 -12.2(3) . . . .
C6 C1 S1 O13 169.8(2) . . . .
C2 C1 S1 O12 111.2(3) . . . .
C6 C1 S1 O12 -66.7(3) . . . .
C2 C1 S1 O11 -130.7(3) . . . .
C6 C1 S1 O11 51.4(3) . . . .
C16 O1 Cu1 N1 -25.7(2) . . . .
C16 O1 Cu1 O11 75.2(3) . . . .
C16 O1 Cu1 N2 153.6(2) . . . .
C16 O1 Cu1 O20 -118.3(2) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305860
