#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/80/7128058.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_7128058
loop_
_publ_author_name
'Sundaravelu, Nallappan'
'Singha, Tushar'
'Nandy, Anuradha'
'Sekar, Govindasamy'
_publ_section_title
;
 Copper-catalyzed domino synthesis of multi-substituted benzo[b]thiophene
 through radical cyclization using xanthate as a sulfur surrogate.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4512
_journal_page_last               4515
_journal_paper_doi               10.1039/d0cc08429h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C16 H12 O S2'
_chemical_formula_weight         284.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-09-10 deposited with the CCDC.	2021-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.311(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9263(10)
_cell_length_b                   12.3383(9)
_cell_length_c                   7.8707(6)
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.95
_cell_volume                     1341.40(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0246
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8986
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.474
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       Block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0360P)²+0.6947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1855
_reflns_number_total             2350
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc08429h2.cif
_cod_data_source_block           69
_cod_depositor_comments
'Adding full bibliography for 7128058--7128060.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7128058
_shelx_shelxl_version_number     2014/7
_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   0.910
_shelx_estimated_absorpt_t_max   0.955
loop_
_space_group_symop_operation_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_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 0.52264(14) 0.15514(17) 0.0925(2) 0.0358(5) Uani 1 1 d . . . . .
C2 C 0.60316(16) 0.20374(18) 0.0344(3) 0.0435(5) Uani 1 1 d . . . . .
H2 H 0.5961 0.2626 -0.0400 0.052 Uiso 1 1 calc R U . . .
C3 C 0.69303(17) 0.1619(2) 0.0907(3) 0.0520(6) Uani 1 1 d . . . . .
H3 H 0.7475 0.1937 0.0546 0.062 Uiso 1 1 calc R U . . .
C4 C 0.70444(17) 0.0732(2) 0.2003(3) 0.0529(6) Uani 1 1 d . . . . .
H4 H 0.7663 0.0469 0.2362 0.064 Uiso 1 1 calc R U . . .
C5 C 0.62620(16) 0.02400(19) 0.2562(3) 0.0449(5) Uani 1 1 d . . . . .
H5 H 0.6342 -0.0357 0.3288 0.054 Uiso 1 1 calc R U . . .
C6 C 0.53382(15) 0.06548(17) 0.2016(2) 0.0352(5) Uani 1 1 d . . . . .
C7 C 0.44294(15) 0.02772(17) 0.2429(2) 0.0355(5) Uani 1 1 d . . . . .
C8 C 0.36377(15) 0.08901(16) 0.1713(2) 0.0358(5) Uani 1 1 d . . . . .
C9 C 0.26516(15) 0.06843(17) 0.1833(2) 0.0386(5) Uani 1 1 d . . . . .
C10 C 0.18912(14) 0.14162(18) 0.0991(3) 0.0397(5) Uani 1 1 d . . . . .
C11 C 0.10704(15) 0.0989(2) 0.0027(3) 0.0477(6) Uani 1 1 d . . . . .
H11 H 0.1012 0.0242 -0.0117 0.057 Uiso 1 1 calc R U . . .
C12 C 0.03431(16) 0.1660(2) -0.0717(3) 0.0546(7) Uani 1 1 d . . . . .
H12 H -0.0194 0.1360 -0.1374 0.066 Uiso 1 1 calc R U . . .
C13 C 0.03987(17) 0.2771(2) -0.0502(3) 0.0539(6) Uani 1 1 d . . . . .
C14 C 0.12149(17) 0.3193(2) 0.0464(3) 0.0527(6) Uani 1 1 d . . . . .
H14 H 0.1265 0.3939 0.0622 0.063 Uiso 1 1 calc R U . . .
C15 C 0.19538(16) 0.25349(19) 0.1194(3) 0.0454(5) Uani 1 1 d . . . . .
H15 H 0.2497 0.2840 0.1826 0.054 Uiso 1 1 calc R U . . .
C16 C -0.0411(2) 0.3503(3) -0.1287(4) 0.0824(10) Uani 1 1 d . . . . .
H16A H -0.0788 0.3735 -0.0414 0.124 Uiso 1 1 calc R U . . .
H16B H -0.0817 0.3113 -0.2157 0.124 Uiso 1 1 calc R U . . .
H16C H -0.0140 0.4124 -0.1786 0.124 Uiso 1 1 calc R U . . .
O1 O 0.43876(12) -0.05977(13) 0.33902(19) 0.0472(4) Uani 1 1 d . . . . .
S1 S 0.40288(4) 0.19498(5) 0.04461(7) 0.04197(18) Uani 1 1 d . . . . .
S2 S 0.22932(4) -0.03966(5) 0.28982(8) 0.0541(2) Uani 1 1 d . . . . .
H1O H 0.375(2) -0.072(3) 0.348(4) 0.095(11) Uiso 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'
S S 0.1246 0.1234 '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
C6 C1 C2 120.6(2) . . ?
C6 C1 S1 112.76(15) . . ?
C2 C1 S1 126.63(17) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 C7 111.50(18) . . ?
C5 C6 C7 128.2(2) . . ?
O1 C7 C8 125.65(19) . . ?
O1 C7 C6 120.13(19) . . ?
C8 C7 C6 114.21(18) . . ?
C7 C8 C9 126.95(19) . . ?
C7 C8 S1 110.09(15) . . ?
C9 C8 S1 122.80(16) . . ?
C8 C9 C10 120.42(19) . . ?
C8 C9 S2 121.88(16) . . ?
C10 C9 S2 117.69(15) . . ?
C15 C10 C11 118.3(2) . . ?
C15 C10 C9 121.49(19) . . ?
C11 C10 C9 120.2(2) . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 118.0(2) . . ?
C12 C13 C16 121.0(3) . . ?
C14 C13 C16 121.0(3) . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C10 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 O1 H1O 107(2) . . ?
C1 S1 C8 91.41(10) . . ?
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
C1 C6 1.397(3) . ?
C1 C2 1.399(3) . ?
C1 S1 1.734(2) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.424(3) . ?
C7 O1 1.324(2) . ?
C7 C8 1.395(3) . ?
C8 C9 1.411(3) . ?
C8 S1 1.772(2) . ?
C9 C10 1.482(3) . ?
C9 S2 1.684(2) . ?
C10 C15 1.391(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(3) . ?
C13 C16 1.513(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O1 H1O 0.91(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
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.2(3) . . . . ?
S1 C1 C2 C3 178.20(16) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
S1 C1 C6 C5 -178.67(15) . . . . ?
C2 C1 C6 C7 -179.07(18) . . . . ?
S1 C1 C6 C7 1.4(2) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
C1 C6 C7 O1 177.00(17) . . . . ?
C5 C6 C7 O1 -2.9(3) . . . . ?
C1 C6 C7 C8 -1.8(2) . . . . ?
C5 C6 C7 C8 178.25(19) . . . . ?
O1 C7 C8 C9 -1.8(3) . . . . ?
C6 C7 C8 C9 176.95(19) . . . . ?
O1 C7 C8 S1 -177.35(16) . . . . ?
C6 C7 C8 S1 1.4(2) . . . . ?
C7 C8 C9 C10 -179.86(19) . . . . ?
S1 C8 C9 C10 -4.9(3) . . . . ?
C7 C8 C9 S2 -0.7(3) . . . . ?
S1 C8 C9 S2 174.25(11) . . . . ?
C8 C9 C10 C15 -49.0(3) . . . . ?
S2 C9 C10 C15 131.87(19) . . . . ?
C8 C9 C10 C11 133.7(2) . . . . ?
S2 C9 C10 C11 -45.4(2) . . . . ?
C15 C10 C11 C12 0.5(3) . . . . ?
C9 C10 C11 C12 177.9(2) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C11 C12 C13 C16 -178.6(2) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C16 C13 C14 C15 179.5(2) . . . . ?
C13 C14 C15 C10 -0.7(3) . . . . ?
C11 C10 C15 C14 0.4(3) . . . . ?
C9 C10 C15 C14 -176.93(19) . . . . ?
C6 C1 S1 C8 -0.53(15) . . . . ?
C2 C1 S1 C8 179.99(18) . . . . ?
C7 C8 S1 C1 -0.50(15) . . . . ?
C9 C8 S1 C1 -176.25(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352627
