#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/63/7226389.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_7226389
loop_
_publ_author_name
'Armaghan, Mahsa'
'Amini, Mostafa M.'
'Khavasi, Hamid Reza'
'Zhang, Wen-Hua'
'Weng, Ng Seik'
_publ_section_title
;
 Inorganic-organic hybrid sorbent for aromatic desulfurization of
 hydro-carbons: Regenerative adsorption based on charge-transfer complex
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA17453A
_journal_year                    2016
_chemical_formula_sum            'C28 H16 Cl2 N2 O6 S'
_chemical_formula_weight         579.40
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2b 2ac'
_symmetry_space_group_name_H-M   'P c n b'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-27 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6317(8)
_cell_length_b                   14.5110(10)
_cell_length_c                   16.1526(9)
_cell_measurement_reflns_used    11048
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.19
_cell_measurement_theta_min      2.29
_cell_volume                     2492.0(3)
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'STOE IPDS IIT'
_diffrn_measurement_method       'rotation method'
_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  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11048
_diffrn_reflns_theta_full        29.19
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         2.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0849P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1658
_reflns_number_gt                1795
_reflns_number_total             3355
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra17453a2.cif
_cod_data_source_block           f:\solution\d62\khd62
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Numerical' changed to
'numerical' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      Pcnb
_cod_original_formula_sum        'C28 H16 Cl2 N2 O6 S1'
_cod_database_code               7226389
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z'
'-x-1/2, y, z-1/2'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.5775(2) 0.0104(2) 0.42576(15) 0.0412(6) Uani 1 1 d .
C2 C 0.6354(2) 0.02253(19) 0.50863(14) 0.0346(5) Uani 1 1 d .
C3 C 0.7634(2) 0.04388(19) 0.51890(15) 0.0383(6) Uani 1 1 d .
C4 C 0.8146(2) 0.0544(2) 0.59712(17) 0.0503(8) Uani 1 1 d .
H4 H 0.8992 0.0694 0.6028 0.060 Uiso 1 1 calc R
C5 C 0.7415(3) 0.0430(2) 0.66613(17) 0.0552(8) Uani 1 1 d .
H5 H 0.7760 0.0495 0.7187 0.066 Uiso 1 1 calc R
C6 C 0.6171(2) 0.0219(2) 0.65673(16) 0.0443(7) Uani 1 1 d .
C7 C 0.5607(2) 0.01176(19) 0.57937(14) 0.0359(6) Uani 1 1 d .
C8 C 0.3876(4) 0.2327(3) 0.4731(3) 0.0839(13) Uani 1 1 d .
C9 C 0.4340(4) 0.2395(2) 0.5562(3) 0.0849(14) Uani 1 1 d .
C10 C 0.3526(5) 0.2246(4) 0.6185(4) 0.1161(19) Uani 1 1 d .
H10 H 0.3807 0.2286 0.6729 0.139 Uiso 1 1 calc R
C11 C 0.2295(6) 0.2038(4) 0.6032(6) 0.149(3) Uani 1 1 d .
H11 H 0.1756 0.1924 0.6474 0.179 Uiso 1 1 calc R
C12 C 0.1840(6) 0.1992(4) 0.5239(8) 0.164(5) Uani 1 1 d .
H12 H 0.0991 0.1866 0.5157 0.197 Uiso 1 1 calc R
C13 C 0.2599(6) 0.2128(3) 0.4562(5) 0.124(2) Uani 1 1 d .
C14 C 0.2123(7) 0.2092(4) 0.3711(6) 0.192(4) Uani 1 1 d .
H14A H 0.2573 0.1630 0.3406 0.231 Uiso 1 1 calc R
H14B H 0.2241 0.2681 0.3451 0.231 Uiso 1 1 calc R
H14C H 0.1243 0.1943 0.3717 0.231 Uiso 1 1 calc R
O1 O 0.63712(19) 0.0164(2) 0.36270(13) 0.0811(9) Uani 1 1 d .
O2 O 0.5047(2) 0.0784(2) 0.76761(14) 0.0760(8) Uani 1 1 d .
O3 O 0.5410(2) -0.0674(2) 0.76351(15) 0.0747(7) Uani 1 1 d .
N1 N 0.5462(2) 0.0095(2) 0.73462(15) 0.0544(7) Uani 1 1 d .
S1 S 0.5000 0.2500 0.39831(14) 0.1115(7) Uani 1 2 d S
Cl1 Cl 0.86638(6) 0.05790(6) 0.43736(4) 0.0529(2) 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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1 C1 C2 122.5(2) . .
O1 C1 C7 118.9(2) . 5_656
C2 C1 C7 118.6(2) . 5_656
C7 C2 C3 118.5(2) . .
C7 C2 C1 119.2(2) . .
C3 C2 C1 122.3(2) . .
C4 C3 C2 120.9(2) . .
C4 C3 Cl1 115.74(19) . .
C2 C3 Cl1 123.41(19) . .
C5 C4 C3 120.4(2) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C6 C5 C4 119.1(2) . .
C6 C5 H5 120.4 . .
C4 C5 H5 120.4 . .
C5 C6 C7 122.7(2) . .
C5 C6 N1 115.3(2) . .
C7 C6 N1 122.0(2) . .
C6 C7 C2 118.4(2) . .
C6 C7 C1 119.5(2) . 5_656
C2 C7 C1 122.1(2) . 5_656
C13 C8 C9 121.7(5) . .
C13 C8 S1 124.2(5) . .
C9 C8 S1 114.2(3) . .
C10 C9 C8 118.0(5) . .
C10 C9 C9 131.5(4) . 2_655
C8 C9 C9 110.5(2) . 2_655
C9 C10 C11 121.1(7) . .
C9 C10 H10 119.4 . .
C11 C10 H10 119.4 . .
C10 C11 C12 121.2(7) . .
C10 C11 H11 119.4 . .
C12 C11 H11 119.4 . .
C11 C12 C13 122.0(6) . .
C11 C12 H12 119.0 . .
C13 C12 H12 119.0 . .
C12 C13 C8 116.1(7) . .
C12 C13 C14 122.6(7) . .
C8 C13 C14 121.3(8) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O3 N1 O2 124.9(3) . .
O3 N1 C6 117.6(3) . .
O2 N1 C6 117.3(3) . .
C8 S1 C8 90.6(3) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.203(3) .
C1 C2 1.484(3) .
C1 C7 1.506(3) 5_656
C2 C7 1.400(3) .
C2 C3 1.406(3) .
C3 C4 1.384(4) .
C3 Cl1 1.725(2) .
C4 C5 1.369(4) .
C4 H4 0.9300 .
C5 C6 1.365(4) .
C5 H5 0.9300 .
C6 C7 1.394(3) .
C6 N1 1.478(4) .
C7 C1 1.506(3) 5_656
C8 C13 1.416(7) .
C8 C9 1.433(7) .
C8 S1 1.718(5) .
C9 C10 1.345(7) .
C9 C9 1.436(8) 2_655
C10 C11 1.366(9) .
C10 H10 0.9300 .
C11 C12 1.372(12) .
C11 H11 0.9300 .
C12 C13 1.373(11) .
C12 H12 0.9300 .
C13 C14 1.466(10) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
O2 N1 1.214(3) .
O3 N1 1.211(4) .
S1 C8 1.717(5) 2_655
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_4
O1 C1 C2 C7 -178.1(3) . .
C7 C1 C2 C7 0.9(4) 5_656 .
O1 C1 C2 C3 1.4(5) . .
C7 C1 C2 C3 -179.6(3) 5_656 .
C7 C2 C3 C4 -0.3(4) . .
C1 C2 C3 C4 -179.8(3) . .
C7 C2 C3 Cl1 179.3(2) . .
C1 C2 C3 Cl1 -0.2(4) . .
C2 C3 C4 C5 0.9(5) . .
Cl1 C3 C4 C5 -178.7(3) . .
C3 C4 C5 C6 -0.6(5) . .
C4 C5 C6 C7 -0.2(5) . .
C4 C5 C6 N1 179.2(3) . .
C5 C6 C7 C2 0.8(4) . .
N1 C6 C7 C2 -178.5(3) . .
C5 C6 C7 C1 -179.2(3) . 5_656
N1 C6 C7 C1 1.4(4) . 5_656
C3 C2 C7 C6 -0.6(4) . .
C1 C2 C7 C6 178.9(3) . .
C3 C2 C7 C1 179.5(3) . 5_656
C1 C2 C7 C1 -1.0(4) . 5_656
C13 C8 C9 C10 1.3(6) . .
S1 C8 C9 C10 -178.4(3) . .
C13 C8 C9 C9 -179.8(4) . 2_655
S1 C8 C9 C9 0.5(5) . 2_655
C8 C9 C10 C11 -0.1(7) . .
C9 C9 C10 C11 -178.7(6) 2_655 .
C9 C10 C11 C12 -1.4(10) . .
C10 C11 C12 C13 1.8(11) . .
C11 C12 C13 C8 -0.6(9) . .
C11 C12 C13 C14 -179.3(6) . .
C9 C8 C13 C12 -0.9(7) . .
S1 C8 C13 C12 178.8(4) . .
C9 C8 C13 C14 177.7(4) . .
S1 C8 C13 C14 -2.6(7) . .
C5 C6 N1 O3 -90.7(4) . .
C7 C6 N1 O3 88.7(3) . .
C5 C6 N1 O2 84.5(3) . .
C7 C6 N1 O2 -96.2(4) . .
C13 C8 S1 C8 -179.9(5) . 2_655
C9 C8 S1 C8 -0.17(18) . 2_655
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202680
