#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/80/7128059.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_7128059
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 H10 O2 S2'
_chemical_formula_weight         298.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-11-12 deposited with the CCDC.	2021-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                88.3339(18)
_cell_angle_beta                 86.4577(18)
_cell_angle_gamma                76.6509(16)
_cell_formula_units_Z            2
_cell_length_a                   6.9373(3)
_cell_length_b                   9.0024(4)
_cell_length_c                   11.0434(5)
_cell_measurement_reflns_used    6286
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.33
_cell_volume                     669.69(5)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_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_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8889
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         1.848
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         8889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1010P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7875
_reflns_number_total             8889
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc08429h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7128058--7128060.cif.'
_cod_database_code               7128059
_shelx_shelxl_version_number     2018/3
_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   0.932
_shelx_estimated_absorpt_t_max   0.954
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.2368(3) 0.6021(2) -0.1812(2) 0.0328(5) Uani 1 1 d . . . . .
C2 C 0.2644(3) 0.5391(3) -0.2971(2) 0.0426(6) Uani 1 1 d . . . . .
H2 H 0.295897 0.433851 -0.306781 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2440(3) 0.6354(3) -0.3959(2) 0.0513(6) Uani 1 1 d . . . . .
H3 H 0.263083 0.594736 -0.473349 0.062 Uiso 1 1 calc R U . . .
C4 C 0.1953(3) 0.7932(3) -0.3825(2) 0.0527(7) Uani 1 1 d . . . . .
H4 H 0.180876 0.855928 -0.451344 0.063 Uiso 1 1 calc R U . . .
C5 C 0.1680(3) 0.8587(3) -0.2694(2) 0.0453(6) Uani 1 1 d . . . . .
H5 H 0.136000 0.964217 -0.261106 0.054 Uiso 1 1 calc R U . . .
C6 C 0.1900(3) 0.7614(2) -0.1676(2) 0.0345(5) Uani 1 1 d . . . . .
C7 C 0.2144(3) 0.6263(2) 0.0313(2) 0.0293(5) Uani 1 1 d . . . . .
C8 C 0.2189(3) 0.5777(2) 0.1545(2) 0.0311(5) Uani 1 1 d . . . . .
C9 C 0.2623(3) 0.4110(2) 0.16875(19) 0.0287(5) Uani 1 1 d . . . . .
C10 C 0.2724(3) 0.3403(2) 0.28365(19) 0.0331(5) Uani 1 1 d . . . . .
H10 H 0.252935 0.399605 0.352817 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3108(3) 0.1839(2) 0.2950(2) 0.0359(5) Uani 1 1 d . . . . .
C12 C 0.3381(3) 0.0939(2) 0.1913(2) 0.0404(6) Uani 1 1 d . . . . .
H12 H 0.362087 -0.011808 0.199308 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3298(3) 0.1605(2) 0.0781(2) 0.0364(5) Uani 1 1 d . . . . .
H13 H 0.348526 0.100241 0.009500 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2933(3) 0.3185(2) 0.06603(19) 0.0299(5) Uani 1 1 d . . . . .
C15 C 0.2482(3) 0.5293(2) -0.06533(19) 0.0299(5) Uani 1 1 d . . . . .
C16 C 0.3017(4) 0.1914(3) 0.5106(2) 0.0543(7) Uani 1 1 d . . . . .
H16A H 0.400623 0.250513 0.509021 0.081 Uiso 1 1 calc R U . . .
H16B H 0.317040 0.123125 0.579569 0.081 Uiso 1 1 calc R U . . .
H16C H 0.172076 0.258465 0.516171 0.081 Uiso 1 1 calc R U . . .
O1 O 0.28796(19) 0.37471(14) -0.05162(13) 0.0328(4) Uani 1 1 d . . . . .
O2 O 0.3244(2) 0.10526(16) 0.40223(15) 0.0500(5) Uani 1 1 d . . . . .
S1 S 0.16463(7) 0.81637(5) -0.01665(5) 0.0367(2) Uani 1 1 d . . . . .
S2 S 0.17859(10) 0.69999(6) 0.26752(5) 0.0539(3) 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'
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
C2 C1 C6 120.2(2) . . ?
C2 C1 C15 130.10(19) . . ?
C6 C1 C15 109.67(19) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 117.9(2) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 S1 126.39(18) . . ?
C1 C6 S1 113.11(16) . . ?
C15 C7 C8 124.30(17) . . ?
C15 C7 S1 111.42(16) . . ?
C8 C7 S1 124.28(16) . . ?
C7 C8 C9 112.74(18) . . ?
C7 C8 S2 122.22(15) . . ?
C9 C8 S2 125.04(16) . . ?
C10 C9 C14 118.43(17) . . ?
C10 C9 C8 121.52(18) . . ?
C14 C9 C8 120.04(18) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O2 C11 C10 124.7(2) . . ?
O2 C11 C12 115.21(18) . . ?
C10 C11 C12 120.0(2) . . ?
C13 C12 C11 120.40(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
O1 C14 C13 115.51(18) . . ?
O1 C14 C9 123.77(17) . . ?
C13 C14 C9 120.72(19) . . ?
O1 C15 C7 122.74(18) . . ?
O1 C15 C1 122.18(18) . . ?
C7 C15 C1 115.07(17) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 O1 C14 116.40(15) . . ?
C11 O2 C16 117.48(16) . . ?
C7 S1 C6 90.72(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 C2 1.400(3) . ?
C1 C6 1.406(3) . ?
C1 C15 1.419(3) . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 S1 1.739(2) . ?
C7 C15 1.373(3) . ?
C7 C8 1.417(3) . ?
C7 S1 1.7393(18) . ?
C8 C9 1.466(3) . ?
C8 S2 1.656(2) . ?
C9 C10 1.402(3) . ?
C9 C14 1.403(3) . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 O2 1.359(3) . ?
C11 C12 1.400(3) . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9300 . ?
C14 O1 1.380(2) . ?
C15 O1 1.361(2) . ?
C16 O2 1.426(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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 -0.3(3) . . . . ?
C15 C1 C2 C3 179.7(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C6 S1 179.58(15) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C15 C1 C6 C5 -179.22(17) . . . . ?
C2 C1 C6 S1 -179.29(15) . . . . ?
C15 C1 C6 S1 0.7(2) . . . . ?
C15 C7 C8 C9 -0.4(3) . . . . ?
S1 C7 C8 C9 179.35(13) . . . . ?
C15 C7 C8 S2 179.52(14) . . . . ?
S1 C7 C8 S2 -0.7(3) . . . . ?
C7 C8 C9 C10 -179.70(16) . . . . ?
S2 C8 C9 C10 0.3(3) . . . . ?
C7 C8 C9 C14 -0.3(3) . . . . ?
S2 C8 C9 C14 179.79(13) . . . . ?
C14 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 C11 179.14(16) . . . . ?
C9 C10 C11 O2 179.61(18) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
O2 C11 C12 C13 -179.30(17) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 O1 179.94(16) . . . . ?
C12 C13 C14 C9 -0.8(3) . . . . ?
C10 C9 C14 O1 -179.74(16) . . . . ?
C8 C9 C14 O1 0.8(3) . . . . ?
C10 C9 C14 C13 1.1(3) . . . . ?
C8 C9 C14 C13 -178.40(17) . . . . ?
C8 C7 C15 O1 0.7(3) . . . . ?
S1 C7 C15 O1 -179.16(13) . . . . ?
C8 C7 C15 C1 -179.91(17) . . . . ?
S1 C7 C15 C1 0.3(2) . . . . ?
C2 C1 C15 O1 -1.2(3) . . . . ?
C6 C1 C15 O1 178.81(15) . . . . ?
C2 C1 C15 C7 179.37(19) . . . . ?
C6 C1 C15 C7 -0.6(2) . . . . ?
C7 C15 O1 C14 -0.1(3) . . . . ?
C1 C15 O1 C14 -179.50(16) . . . . ?
C13 C14 O1 C15 178.63(15) . . . . ?
C9 C14 O1 C15 -0.6(3) . . . . ?
C10 C11 O2 C16 -1.5(3) . . . . ?
C12 C11 O2 C16 178.78(17) . . . . ?
C15 C7 S1 C6 0.11(14) . . . . ?
C8 C7 S1 C6 -179.70(17) . . . . ?
C5 C6 S1 C7 179.43(19) . . . . ?
C1 C6 S1 C7 -0.48(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352628
