#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/80/7128060.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_7128060
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            'C17 H15 N O S2'
_chemical_formula_weight         313.42
_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   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                105.2378(17)
_cell_angle_beta                 102.3386(17)
_cell_angle_gamma                91.2454(18)
_cell_formula_units_Z            2
_cell_length_a                   9.1370(3)
_cell_length_b                   9.3396(4)
_cell_length_c                   9.3410(3)
_cell_measurement_reflns_used    6231
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.77
_cell_volume                     748.76(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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0216
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11007
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.268
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0449P)²+0.2709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2248
_reflns_number_total             2625
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc08429h2.cif
_cod_data_source_block           925
_cod_depositor_comments
'Adding full bibliography for 7128058--7128060.cif.'
_cod_database_code               7128060
_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   0.917
_shelx_estimated_absorpt_t_max   0.949
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 0.2236(2) 0.4528(2) 0.4782(2) 0.0550(5) Uani 1 1 d . . . . .
H1 H 0.1829 0.5228 0.4297 0.066 Uiso 1 1 calc R U . . .
C2 C 0.1767(2) 0.4339(2) 0.6014(3) 0.0615(5) Uani 1 1 d . . . . .
H2 H 0.1044 0.4924 0.6379 0.074 Uiso 1 1 calc R U . . .
C3 C 0.2358(2) 0.3279(3) 0.6734(3) 0.0625(6) Uani 1 1 d . . . . .
H3 H 0.2019 0.3168 0.7572 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3427(2) 0.2398(2) 0.6235(2) 0.0572(5) Uani 1 1 d . . . . .
H4 H 0.3811 0.1688 0.6717 0.069 Uiso 1 1 calc R U . . .
C5 C 0.3923(2) 0.2595(2) 0.4982(2) 0.0454(4) Uani 1 1 d . . . . .
C6 C 0.50929(19) 0.26798(19) 0.28023(18) 0.0407(4) Uani 1 1 d . . . . .
C7 C 0.40014(19) 0.36811(19) 0.3007(2) 0.0419(4) Uani 1 1 d . . . . .
C8 C 0.33391(19) 0.36557(19) 0.4254(2) 0.0429(4) Uani 1 1 d . . . . .
C9 C 0.58888(19) 0.23765(19) 0.16134(19) 0.0409(4) Uani 1 1 d . . . . .
C10 C 0.70410(19) 0.13004(19) 0.15928(18) 0.0397(4) Uani 1 1 d . . . . .
C11 C 0.8165(2) 0.1322(2) 0.2878(2) 0.0471(4) Uani 1 1 d . . . . .
H11 H 0.8164 0.2012 0.3800 0.056 Uiso 1 1 calc R U . . .
C12 C 0.9271(2) 0.0349(2) 0.2816(2) 0.0490(5) Uani 1 1 d . . . . .
H12 H 1.0025 0.0421 0.3682 0.059 Uiso 1 1 calc R U . . .
C13 C 0.92848(19) -0.0753(2) 0.1464(2) 0.0433(4) Uani 1 1 d . . . . .
C14 C 0.81635(19) -0.0757(2) 0.0169(2) 0.0446(4) Uani 1 1 d . . . . .
H14 H 0.8141 -0.1463 -0.0749 0.053 Uiso 1 1 calc R U . . .
C15 C 0.71047(19) 0.02574(19) 0.02365(19) 0.0426(4) Uani 1 1 d . . . . .
H15 H 0.6406 0.0251 -0.0650 0.051 Uiso 1 1 calc R U . . .
C16 C 1.1543(3) -0.1712(3) 0.2697(3) 0.0746(7) Uani 1 1 d . . . . .
H16A H 1.2109 -0.0760 0.2998 0.112 Uiso 1 1 calc R U . . .
H16B H 1.2189 -0.2486 0.2427 0.112 Uiso 1 1 calc R U . . .
H16C H 1.1140 -0.1842 0.3527 0.112 Uiso 1 1 calc R U . . .
C17 C 1.0278(2) -0.2932(2) 0.0005(3) 0.0655(6) Uani 1 1 d . . . . .
H17A H 0.9357 -0.3556 -0.0262 0.098 Uiso 1 1 calc R U . . .
H17B H 1.1116 -0.3523 0.0151 0.098 Uiso 1 1 calc R U . . .
H17C H 1.0328 -0.2483 -0.0799 0.098 Uiso 1 1 calc R U . . .
N1 N 1.03270(18) -0.17807(19) 0.13996(19) 0.0539(4) Uani 1 1 d . . . . .
O1 O 0.35421(16) 0.45963(15) 0.21515(17) 0.0570(4) Uani 1 1 d . . . . .
S1 S 0.52871(6) 0.16584(6) 0.41672(5) 0.05044(16) Uani 1 1 d . . . . .
S2 S 0.54830(6) 0.31811(6) 0.01866(6) 0.05773(18) Uani 1 1 d . . . . .
H1O H 0.406(3) 0.432(3) 0.131(4) 0.114(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'
N N 0.0061 0.0033 '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 C8 119.15(19) . . ?
C2 C1 H1 120.4 . . ?
C8 C1 H1 120.4 . . ?
C1 C2 C3 120.73(19) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C4 C5 C8 120.90(17) . . ?
C4 C5 S1 126.90(15) . . ?
C8 C5 S1 112.19(14) . . ?
C7 C6 C9 127.36(16) . . ?
C7 C6 S1 110.27(13) . . ?
C9 C6 S1 122.18(13) . . ?
O1 C7 C6 126.11(17) . . ?
O1 C7 C8 120.00(16) . . ?
C6 C7 C8 113.88(16) . . ?
C5 C8 C1 119.66(18) . . ?
C5 C8 C7 111.89(16) . . ?
C1 C8 C7 128.46(18) . . ?
C6 C9 C10 120.12(15) . . ?
C6 C9 S2 120.81(14) . . ?
C10 C9 S2 119.02(13) . . ?
C15 C10 C11 116.89(16) . . ?
C15 C10 C9 120.29(15) . . ?
C11 C10 C9 122.71(16) . . ?
C12 C11 C10 121.71(17) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 121.17(16) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
N1 C13 C12 122.06(16) . . ?
N1 C13 C14 121.09(17) . . ?
C12 C13 C14 116.85(16) . . ?
C15 C14 C13 121.20(17) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C10 122.04(16) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 N1 C16 121.11(17) . . ?
C13 N1 C17 120.69(16) . . ?
C16 N1 C17 118.15(17) . . ?
C7 O1 H1O 104.5(18) . . ?
C5 S1 C6 91.77(8) . . ?
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 1.362(3) . ?
C1 C8 1.400(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.394(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C8 1.396(3) . ?
C5 S1 1.7328(18) . ?
C6 C7 1.391(2) . ?
C6 C9 1.425(3) . ?
C6 S1 1.7654(17) . ?
C7 O1 1.333(2) . ?
C7 C8 1.428(3) . ?
C9 C10 1.471(2) . ?
C9 S2 1.6750(17) . ?
C10 C15 1.394(2) . ?
C10 C11 1.399(2) . ?
C11 C12 1.373(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.406(3) . ?
C12 H12 0.9300 . ?
C13 N1 1.366(2) . ?
C13 C14 1.407(2) . ?
C14 C15 1.368(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N1 1.445(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N1 1.446(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O1 H1O 0.98(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
C8 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C8 -0.4(3) . . . . ?
C3 C4 C5 S1 178.34(16) . . . . ?
C9 C6 C7 O1 -3.1(3) . . . . ?
S1 C6 C7 O1 -178.07(14) . . . . ?
C9 C6 C7 C8 175.92(16) . . . . ?
S1 C6 C7 C8 0.93(19) . . . . ?
C4 C5 C8 C1 -0.3(3) . . . . ?
S1 C5 C8 C1 -179.19(14) . . . . ?
C4 C5 C8 C7 179.75(17) . . . . ?
S1 C5 C8 C7 0.88(19) . . . . ?
C2 C1 C8 C5 0.9(3) . . . . ?
C2 C1 C8 C7 -179.18(18) . . . . ?
O1 C7 C8 C5 177.88(15) . . . . ?
C6 C7 C8 C5 -1.2(2) . . . . ?
O1 C7 C8 C1 -2.0(3) . . . . ?
C6 C7 C8 C1 178.90(17) . . . . ?
C7 C6 C9 C10 178.51(16) . . . . ?
S1 C6 C9 C10 -7.0(2) . . . . ?
C7 C6 C9 S2 -4.0(3) . . . . ?
S1 C6 C9 S2 170.48(9) . . . . ?
C6 C9 C10 C15 136.16(17) . . . . ?
S2 C9 C10 C15 -41.4(2) . . . . ?
C6 C9 C10 C11 -47.8(2) . . . . ?
S2 C9 C10 C11 134.63(16) . . . . ?
C15 C10 C11 C12 -0.8(3) . . . . ?
C9 C10 C11 C12 -176.94(17) . . . . ?
C10 C11 C12 C13 -2.6(3) . . . . ?
C11 C12 C13 N1 -176.39(18) . . . . ?
C11 C12 C13 C14 3.3(3) . . . . ?
N1 C13 C14 C15 179.01(16) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C10 -2.8(3) . . . . ?
C11 C10 C15 C14 3.4(3) . . . . ?
C9 C10 C15 C14 179.70(16) . . . . ?
C12 C13 N1 C16 -4.9(3) . . . . ?
C14 C13 N1 C16 175.46(19) . . . . ?
C12 C13 N1 C17 177.79(18) . . . . ?
C14 C13 N1 C17 -1.9(3) . . . . ?
C4 C5 S1 C6 -179.10(18) . . . . ?
C8 C5 S1 C6 -0.31(14) . . . . ?
C7 C6 S1 C5 -0.35(13) . . . . ?
C9 C6 S1 C5 -175.65(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352629
