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#$Date: 2025-08-22 11:56:18 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301860 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/60/7126067.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_7126067
loop_
_publ_author_name
'Reddy, Mandapati Bhargava'
'Anandhan, Ramasamy'
_publ_section_title
;
 Visible light initiated amino group ortho-directed copper(i)-catalysed
 aerobic oxidative C(sp)-S coupling reaction: synthesis of substituted
 2-phenylbenzothiazoles via thia-Wolff rearrangement.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3781
_journal_page_last               3784
_journal_paper_doi               10.1039/d0cc00815j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C14 H10 Cl N S'
_chemical_formula_sum            'C14 H10 Cl N S'
_chemical_formula_weight         259.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc23hdfg
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2019-09-13 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.333(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9940(9)
_cell_length_b                   5.8548(6)
_cell_length_c                   25.946(2)
_cell_measurement_reflns_used    3648
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.224
_cell_measurement_theta_min      1.571
_cell_volume                     1213.4(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            16223
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.224
_diffrn_reflns_theta_min         1.571
_exptl_absorpt_coefficient_mu    0.460
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0675
_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)+(0.0639P)²+0.3005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1724
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2112
_reflns_number_total             3648
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc00815j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7126067.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7126067
_shelx_shelxl_version_number     2016/4
_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   0.882
_shelx_estimated_absorpt_t_max   0.926
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_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
S1 S 0.00287(10) 0.88474(13) 0.15574(3) 0.0529(3) Uani 1 1 d . . . . .
CL1 Cl -0.39317(10) 1.82632(14) -0.08456(3) 0.0605(3) Uani 1 1 d . . . . .
C1 C -0.0137(3) 1.0169(4) 0.21708(10) 0.0405(6) Uani 1 1 d . . . . .
C9 C -0.1852(3) 1.3587(5) 0.04007(10) 0.0425(6) Uani 1 1 d . . . . .
C12 C -0.3115(3) 1.6463(5) -0.03651(10) 0.0432(6) Uani 1 1 d . . . . .
C2 C -0.0975(3) 0.8979(5) 0.25435(11) 0.0459(7) Uani 1 1 d . . . . .
H2 H -0.151092 0.761649 0.245506 0.055 Uiso 1 1 calc R U . . .
N1 N 0.1563(3) 1.3415(4) 0.19413(10) 0.0599(7) Uani 1 1 d . . . . .
H1A H 0.206340 1.466549 0.202844 0.072 Uiso 1 1 calc R U . . .
H1B H 0.161560 1.290808 0.163126 0.072 Uiso 1 1 calc R U . . .
C7 C -0.0740(3) 1.0816(5) 0.11375(11) 0.0477(7) Uani 1 1 d . . . . .
C6 C 0.0682(3) 1.2229(5) 0.22967(10) 0.0409(6) Uani 1 1 d . . . . .
C5 C 0.0580(3) 1.3019(5) 0.28017(11) 0.0484(7) Uani 1 1 d . . . . .
H5 H 0.108697 1.439773 0.289421 0.058 Uiso 1 1 calc R U . . .
C13 C -0.2414(4) 1.4414(5) -0.04999(10) 0.0475(7) Uani 1 1 d . . . . .
H13 H -0.237478 1.399232 -0.084478 0.057 Uiso 1 1 calc R U . . .
C14 C -0.1771(3) 1.2995(5) -0.01178(11) 0.0480(7) Uani 1 1 d . . . . .
H14 H -0.127549 1.162124 -0.020707 0.058 Uiso 1 1 calc R U . . .
C11 C -0.3193(3) 1.7109(5) 0.01431(10) 0.0476(7) Uani 1 1 d . . . . .
H11 H -0.367175 1.849870 0.022854 0.057 Uiso 1 1 calc R U . . .
C10 C -0.2558(4) 1.5681(5) 0.05240(11) 0.0486(7) Uani 1 1 d . . . . .
H10 H -0.259976 1.611898 0.086776 0.058 Uiso 1 1 calc R U . . .
C3 C -0.1030(3) 0.9775(6) 0.30430(11) 0.0527(7) Uani 1 1 d . . . . .
H3 H -0.158111 0.895811 0.329232 0.063 Uiso 1 1 calc R U . . .
C4 C -0.0245(4) 1.1817(6) 0.31625(12) 0.0554(8) Uani 1 1 d . . . . .
H4 H -0.027911 1.238484 0.349660 0.066 Uiso 1 1 calc R U . . .
C8 C -0.1226(3) 1.2076(5) 0.08007(11) 0.0490(7) 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'
Cl Cl 0.1484 0.1585 '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'
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
C7 S1 C1 104.02(13) . . ?
C2 C1 C6 120.2(2) . . ?
C2 C1 S1 117.5(2) . . ?
C6 C1 S1 122.0(2) . . ?
C10 C9 C14 118.4(3) . . ?
C10 C9 C8 120.5(3) . . ?
C14 C9 C8 121.0(3) . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 CL1 119.4(2) . . ?
C11 C12 CL1 119.4(2) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C6 N1 H1A 120.0 . . ?
C6 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C8 C7 S1 173.4(3) . . ?
N1 C6 C5 121.0(3) . . ?
N1 C6 C1 121.7(2) . . ?
C5 C6 C1 117.3(2) . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C9 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C7 C8 C9 178.5(3) . . ?
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 C7 1.684(3) . ?
S1 C1 1.780(3) . ?
CL1 C12 1.739(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.405(4) . ?
C9 C10 1.392(4) . ?
C9 C14 1.393(4) . ?
C9 C8 1.438(4) . ?
C12 C13 1.375(4) . ?
C12 C11 1.376(4) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
N1 C6 1.372(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C7 C8 1.196(4) . ?
C6 C5 1.395(4) . ?
C5 C4 1.363(4) . ?
C5 H5 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C11 C10 1.376(4) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
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
C7 S1 C1 C2 126.3(2) . . . . ?
C7 S1 C1 C6 -60.0(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
S1 C1 C2 C3 173.9(2) . . . . ?
C2 C1 C6 N1 178.1(2) . . . . ?
S1 C1 C6 N1 4.5(4) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
S1 C1 C6 C5 -174.85(19) . . . . ?
N1 C6 C5 C4 -177.8(3) . . . . ?
C1 C6 C5 C4 1.6(4) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
CL1 C12 C13 C14 -179.9(2) . . . . ?
C12 C13 C14 C9 1.3(4) . . . . ?
C10 C9 C14 C13 -1.8(4) . . . . ?
C8 C9 C14 C13 178.2(3) . . . . ?
C13 C12 C11 C10 0.1(4) . . . . ?
CL1 C12 C11 C10 179.6(2) . . . . ?
C12 C11 C10 C9 -0.6(4) . . . . ?
C14 C9 C10 C11 1.4(4) . . . . ?
C8 C9 C10 C11 -178.5(3) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C6 C5 C4 C3 -0.6(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168351760
