#------------------------------------------------------------------------------
#$Date: 2025-08-20 23:21:57 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301837 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/17/4311785.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_4311785
loop_
_publ_author_name
'R. Cejudo-Marín'
'G. Alzuet'
'S. Ferrer'
'J. Borrás'
'A. Castiñeiras'
'E. Monzani'
'L. Casella'
_publ_contact_author
;
      Santiago García-Granda
      Departamento de Química Física y Analítica
      Facultad de Química
      Universidad de Oviedo
      Avda. Julián Clavería, 8
      33071 Oviedo
      Spain
;
_publ_contact_author_email       sgg@sauron.quimica.uniovi.es
_publ_contact_author_fax         '0034 98 5103125'
_publ_contact_author_phone       '0034 98 5103477'
_publ_section_title
;
 Functional Superoxide Dismutase Mimics. Structural Characterization and
 Magnetic Exchange Interactions of Copper(II)-N-Substituted Sulfonamide
 Dimer Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6805
_journal_page_last               6814
_journal_paper_doi               10.1021/ic049718w
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C13 H10 N2 O2 S2'
_chemical_formula_weight         290.35
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.993(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8179(15)
_cell_length_b                   9.1246(11)
_cell_length_c                   11.0332(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.42
_cell_measurement_theta_min      12.66
_cell_volume                     1290.2(2)
_computing_cell_refinement       'CAD4-Express Software (Nonius, 1994)'
_computing_data_collection       'CAD4-Express Software (Nonius, 1994)'
_computing_data_reduction        'GENHKL (Kretschmar, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'MACH3 Enraf Nonius'
_diffrn_measurement_method       omega/2theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0050
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5452
_diffrn_reflns_theta_full        72.89
_diffrn_reflns_theta_max         72.89
_diffrn_reflns_theta_min         3.45
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.742
_exptl_absorpt_correction_T_max  0.5216
_exptl_absorpt_correction_T_min  0.3806
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0348
_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)+(0.0538P)²+0.6099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1039
_reflns_number_gt                2257
_reflns_number_total             2582
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic049718wsi20040304_101648_1.cif
_cod_data_source_block           02jb01
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'psi-scans' was replaced
with 'psi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4311785
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33370(4) 0.28150(6) 0.71716(5) 0.04777(18) Uani 1 1 d . . .
S2 S 0.35304(4) 0.63890(5) 0.72221(4) 0.03857(16) Uani 1 1 d . . .
O11 O 0.34468(12) 0.56730(17) 0.83798(13) 0.0489(4) Uani 1 1 d . . .
O12 O 0.40013(13) 0.78130(15) 0.71797(16) 0.0548(4) Uani 1 1 d . . .
N11 N 0.44466(13) 0.31778(17) 0.53352(15) 0.0381(4) Uani 1 1 d . . .
H11A H 0.4939 0.3609 0.4782 0.046 Uiso 1 1 d R . .
N12 N 0.41536(13) 0.54070(16) 0.62661(15) 0.0397(4) Uani 1 1 d . . .
C1 C 0.3656(2) 0.1312(2) 0.6293(2) 0.0541(6) Uani 1 1 d . . .
H1 H 0.3518 0.0292 0.6532 0.065 Uiso 1 1 d R . .
C2 C 0.42439(17) 0.1696(2) 0.5369(2) 0.0466(5) Uani 1 1 d . . .
H2 H 0.4564 0.1105 0.4740 0.056 Uiso 1 1 d R . .
C3 C 0.40245(14) 0.3961(2) 0.62270(16) 0.0345(4) Uani 1 1 d . . .
C4 C 0.22514(15) 0.6566(2) 0.66184(17) 0.0376(4) Uani 1 1 d . . .
C5 C 0.14538(16) 0.5796(2) 0.71145(18) 0.0410(4) Uani 1 1 d . . .
H5 H 0.1591 0.5124 0.7756 0.049 Uiso 1 1 d R . .
C6 C 0.04188(16) 0.5947(2) 0.66572(18) 0.0443(5) Uani 1 1 d . . .
C7 C -0.04224(19) 0.5162(3) 0.7146(3) 0.0596(6) Uani 1 1 d . . .
H7 H -0.0227 0.4491 0.7895 0.072 Uiso 1 1 d R . .
C8 C -0.1407(2) 0.5340(4) 0.6683(3) 0.0737(8) Uani 1 1 d . . .
H8 H -0.2033 0.4828 0.7050 0.088 Uiso 1 1 d R . .
C9 C -0.1599(2) 0.6316(4) 0.5738(3) 0.0769(9) Uani 1 1 d . . .
H9 H -0.2350 0.6360 0.5465 0.092 Uiso 1 1 d R . .
C10 C -0.0811(2) 0.7089(4) 0.5238(2) 0.0702(8) Uani 1 1 d . . .
H10 H -0.0990 0.7818 0.4594 0.084 Uiso 1 1 d R . .
C11 C 0.02331(18) 0.6927(3) 0.5686(2) 0.0507(5) Uani 1 1 d . . .
C12 C 0.1081(2) 0.7687(3) 0.5186(2) 0.0579(6) Uani 1 1 d . . .
H12 H 0.0920 0.8480 0.4531 0.070 Uiso 1 1 d R . .
C13 C 0.20725(19) 0.7523(3) 0.5627(2) 0.0501(5) Uani 1 1 d . . .
H13 H 0.2648 0.8044 0.5289 0.060 Uiso 1 1 d R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
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
C3 S1 C1 90.81(10) . . ?
O12 S2 O11 118.54(10) . . ?
O12 S2 N12 105.64(9) . . ?
O11 S2 N12 112.00(9) . . ?
O12 S2 C4 107.06(9) . . ?
O11 S2 C4 107.04(9) . . ?
N12 S2 C4 105.79(9) . . ?
C3 N11 C2 115.20(17) . . ?
C3 N11 H11A 121.5 . . ?
C2 N11 H11A 122.7 . . ?
C3 N12 S2 120.75(14) . . ?
C2 C1 S1 111.35(17) . . ?
C2 C1 H1 124.3 . . ?
S1 C1 H1 123.6 . . ?
C1 C2 N11 112.96(19) . . ?
C1 C2 H2 130.8 . . ?
N11 C2 H2 116.2 . . ?
N12 C3 N11 120.14(17) . . ?
N12 C3 S1 130.17(15) . . ?
N11 C3 S1 109.68(13) . . ?
C5 C4 C13 121.05(19) . . ?
C5 C4 S2 119.95(15) . . ?
C13 C4 S2 119.00(16) . . ?
C4 C5 C6 120.72(19) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C11 119.5(2) . . ?
C7 C6 C5 122.1(2) . . ?
C11 C6 C5 118.4(2) . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 124.7 . . ?
C6 C7 H7 114.9 . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 121.8 . . ?
C9 C8 H8 117.5 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 125.0 . . ?
C8 C9 H9 114.0 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 118.2 . . ?
C11 C10 H10 121.3 . . ?
C12 C11 C6 119.2(2) . . ?
C12 C11 C10 122.6(2) . . ?
C6 C11 C10 118.3(2) . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 118.0 . . ?
C12 C13 C4 118.8(2) . . ?
C12 C13 H13 121.8 . . ?
C4 C13 H13 119.4 . . ?
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
S1 C3 1.7288(19) . ?
S1 C1 1.733(2) . ?
S2 O12 1.4338(15) . ?
S2 O11 1.4403(15) . ?
S2 N12 1.6071(16) . ?
S2 C4 1.766(2) . ?
N11 C3 1.338(2) . ?
N11 C2 1.378(3) . ?
N11 H11A 0.9692 . ?
N12 C3 1.330(2) . ?
C1 C2 1.325(3) . ?
C1 H1 0.9837 . ?
C2 H2 0.9744 . ?
C4 C5 1.363(3) . ?
C4 C13 1.416(3) . ?
C5 C6 1.418(3) . ?
C5 H5 0.9501 . ?
C6 C7 1.410(3) . ?
C6 C11 1.413(3) . ?
C7 C8 1.363(4) . ?
C7 H7 1.0547 . ?
C8 C9 1.390(5) . ?
C8 H8 1.0177 . ?
C9 C10 1.357(5) . ?
C9 H9 1.0034 . ?
C10 C11 1.426(3) . ?
C10 H10 0.9973 . ?
C11 C12 1.409(4) . ?
C12 C13 1.361(4) . ?
C12 H12 1.0406 . ?
C13 H13 0.9578 . ?
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
N11 H11A N12 0.97 1.88 2.849(2) 175.4 3_666
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
_geom_torsion_publ_flag
O12 S2 N12 C3 168.89(16) . . . . ?
O11 S2 N12 C3 38.48(19) . . . . ?
C4 S2 N12 C3 -77.80(17) . . . . ?
C3 S1 C1 C2 0.31(19) . . . . ?
S1 C1 C2 N11 -0.3(3) . . . . ?
C3 N11 C2 C1 0.1(3) . . . . ?
S2 N12 C3 N11 171.85(14) . . . . ?
S2 N12 C3 S1 -6.6(3) . . . . ?
C2 N11 C3 N12 -178.61(18) . . . . ?
C2 N11 C3 S1 0.1(2) . . . . ?
C1 S1 C3 N12 178.3(2) . . . . ?
C1 S1 C3 N11 -0.25(15) . . . . ?
O12 S2 C4 C5 -142.00(16) . . . . ?
O11 S2 C4 C5 -13.92(18) . . . . ?
N12 S2 C4 C5 105.68(16) . . . . ?
O12 S2 C4 C13 37.44(19) . . . . ?
O11 S2 C4 C13 165.53(16) . . . . ?
N12 S2 C4 C13 -74.88(18) . . . . ?
C13 C4 C5 C6 -0.7(3) . . . . ?
S2 C4 C5 C6 178.73(15) . . . . ?
C4 C5 C6 C7 179.7(2) . . . . ?
C4 C5 C6 C11 -0.7(3) . . . . ?
C11 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C7 C8 179.8(2) . . . . ?
C6 C7 C8 C9 -1.2(4) . . . . ?
C7 C8 C9 C10 1.4(4) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C7 C6 C11 C12 -178.8(2) . . . . ?
C5 C6 C11 C12 1.6(3) . . . . ?
C7 C6 C11 C10 0.3(3) . . . . ?
C5 C6 C11 C10 -179.2(2) . . . . ?
C9 C10 C11 C12 179.0(3) . . . . ?
C9 C10 C11 C6 -0.1(4) . . . . ?
C6 C11 C12 C13 -1.1(4) . . . . ?
C10 C11 C12 C13 179.8(2) . . . . ?
C11 C12 C13 C4 -0.3(4) . . . . ?
C5 C4 C13 C12 1.2(3) . . . . ?
S2 C4 C13 C12 -178.19(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1689900
2 PubChem 2259517
