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#$Date: 2022-08-06 15:02:40 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277137 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158766.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_7158766
loop_
_publ_author_name
'Ravi Singh, Krishna'
'Santhosh, Chikkappaiahnayaka'
'Swaroop, Toreshettahally R.'
'Sadashiva, Maralinganadoddi P.'
_publ_section_title
;
 The regioselective synthesis of 2,5- and 4,5-disubstituted thiazoles
 via the cyclization of 2-oxo-2-(amino)ethanedithioates with
 isocyanides.
;
_journal_issue                   29
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5771
_journal_page_last               5778
_journal_paper_doi               10.1039/d2ob00837h
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C13 H11 Br N2 O3 S'
_chemical_formula_sum            'C13 H11 Br N2 O3 S'
_chemical_formula_weight         355.21
_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   geom
_audit_creation_date             2021-09-26
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c4697 for OlexSys, GUI svn.r6394)
;
_audit_update_record
;
2021-11-01 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.190(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5681(4)
_cell_length_b                   14.0924(9)
_cell_length_c                   15.4674(10)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      70.17
_cell_measurement_theta_min      4.25
_cell_volume                     1427.84(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23502
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.436
_diffrn_reflns_theta_min         4.249
_exptl_absorpt_coefficient_mu    5.380
_exptl_absorpt_correction_T_max  0.6617
_exptl_absorpt_correction_T_min  0.2288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1534 before and 0.0921 after correction.
The Ratio of minimum to maximum transmission is 0.3458.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.947
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.330
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.330
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0686
_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)+5.7894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2295
_reflns_number_total             2689
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00837h2.cif
_cod_data_source_block           4b
_cod_depositor_comments
'Adding full bibliography for 7158765--7158766.cif.'
_cod_database_code               7158766
_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_max   0.499
_shelx_estimated_absorpt_t_min   0.413
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C6(H6), C7(H7), C4(H4), C3(H3), C13(H13)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Br1 Br 1.12946(10) 0.41802(6) 0.90936(5) 0.0692(3) Uani 1 1 d . . . . .
S12 S -0.1053(2) 0.63900(12) 0.60033(11) 0.0576(4) Uani 1 1 d . . . . .
O18 O -0.2409(6) 0.3084(3) 0.5728(3) 0.0504(10) Uani 1 1 d . . . . .
O17 O 0.0740(6) 0.3185(3) 0.6376(3) 0.0595(11) Uani 1 1 d . . . . .
N8 N 0.3189(7) 0.4653(3) 0.6990(3) 0.0471(11) Uani 1 1 d . . . . .
H8 H 0.266002 0.412640 0.680426 0.056 Uiso 1 1 calc R U . . .
N14 N -0.2935(7) 0.4880(4) 0.5522(3) 0.0520(12) Uani 1 1 d . . . . .
O10 O 0.2689(8) 0.6251(3) 0.6959(4) 0.0865(18) Uani 1 1 d . . . . .
C5 C 0.5066(8) 0.4588(4) 0.7486(4) 0.0405(12) Uani 1 1 d . . . . .
C6 C 0.6202(9) 0.5372(4) 0.7793(4) 0.0516(14) Uani 1 1 d . . . . .
H6 H 0.572455 0.598281 0.767394 0.062 Uiso 1 1 calc R U . . .
C7 C 0.8040(9) 0.5238(5) 0.8274(4) 0.0534(15) Uani 1 1 d . . . . .
H7 H 0.878559 0.575944 0.848695 0.064 Uiso 1 1 calc R U . . .
C2 C 0.8763(8) 0.4337(5) 0.8437(4) 0.0494(14) Uani 1 1 d . . . . .
C16 C -0.0798(8) 0.3562(4) 0.6051(4) 0.0435(12) Uani 1 1 d . . . . .
C15 C -0.1134(8) 0.4597(4) 0.5962(4) 0.0438(12) Uani 1 1 d . . . . .
C4 C 0.5845(9) 0.3688(4) 0.7660(4) 0.0523(15) Uani 1 1 d . . . . .
H4 H 0.511465 0.316125 0.744951 0.063 Uiso 1 1 calc R U . . .
C3 C 0.7671(9) 0.3558(5) 0.8136(4) 0.0527(15) Uani 1 1 d . . . . .
H3 H 0.816344 0.294965 0.825258 0.063 Uiso 1 1 calc R U . . .
C11 C 0.0112(8) 0.5329(4) 0.6268(4) 0.0462(13) Uani 1 1 d . . . . .
C9 C 0.2132(9) 0.5442(4) 0.6773(4) 0.0506(14) Uani 1 1 d . . . . .
C13 C -0.3059(9) 0.5802(5) 0.5500(4) 0.0561(16) Uani 1 1 d . . . . .
H13 H -0.417104 0.611722 0.522578 0.067 Uiso 1 1 calc R U . . .
C19 C -0.2310(10) 0.2046(4) 0.5783(4) 0.0563(16) Uani 1 1 d . . . . .
H19A H -0.215333 0.184255 0.638350 0.068 Uiso 1 1 calc R U . . .
H19B H -0.116671 0.180698 0.548495 0.068 Uiso 1 1 calc R U . . .
C20 C -0.4295(12) 0.1691(5) 0.5355(5) 0.076(2) Uani 1 1 d . . . . .
H20A H -0.443122 0.190306 0.476358 0.115 Uiso 1 1 calc R U . . .
H20B H -0.540894 0.193346 0.565792 0.115 Uiso 1 1 calc R U . . .
H20C H -0.431276 0.101006 0.536955 0.115 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C13 S12 C11 90.1(3) . . ?
C16 O18 C19 117.1(4) . . ?
C5 N8 H8 116.3 . . ?
C9 N8 H8 116.3 . . ?
C9 N8 C5 127.4(5) . . ?
C13 N14 C15 110.5(5) . . ?
C6 C5 N8 124.0(5) . . ?
C4 C5 N8 117.5(5) . . ?
C4 C5 C6 118.5(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.9(6) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.9 . . ?
C2 C7 C6 120.1(6) . . ?
C2 C7 H7 119.9 . . ?
C7 C2 Br1 119.0(5) . . ?
C7 C2 C3 120.7(5) . . ?
C3 C2 Br1 120.3(5) . . ?
O18 C16 C15 111.0(4) . . ?
O17 C16 O18 123.4(5) . . ?
O17 C16 C15 125.6(5) . . ?
N14 C15 C16 116.5(5) . . ?
C11 C15 N14 114.8(5) . . ?
C11 C15 C16 128.7(5) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 H4 119.3 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.3(6) . . ?
C4 C3 H3 120.3 . . ?
C15 C11 S12 109.1(4) . . ?
C15 C11 C9 137.7(5) . . ?
C9 C11 S12 113.2(4) . . ?
N8 C9 C11 117.7(5) . . ?
O10 C9 N8 125.0(5) . . ?
O10 C9 C11 117.3(5) . . ?
S12 C13 H13 122.3 . . ?
N14 C13 S12 115.5(4) . . ?
N14 C13 H13 122.3 . . ?
O18 C19 H19A 110.6 . . ?
O18 C19 H19B 110.6 . . ?
O18 C19 C20 105.8(5) . . ?
H19A C19 H19B 108.7 . . ?
C20 C19 H19A 110.6 . . ?
C20 C19 H19B 110.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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
Br1 C2 1.897(5) . ?
S12 C11 1.715(6) . ?
S12 C13 1.697(6) . ?
O18 C16 1.321(6) . ?
O18 C19 1.466(7) . ?
O17 C16 1.217(6) . ?
N8 H8 0.8600 . ?
N8 C5 1.406(6) . ?
N8 C9 1.341(7) . ?
N14 C15 1.380(7) . ?
N14 C13 1.303(8) . ?
O10 C9 1.225(7) . ?
C5 C6 1.397(8) . ?
C5 C4 1.386(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(8) . ?
C7 H7 0.9300 . ?
C7 C2 1.372(9) . ?
C2 C3 1.374(9) . ?
C16 C15 1.481(8) . ?
C15 C11 1.378(8) . ?
C4 H4 0.9300 . ?
C4 C3 1.373(8) . ?
C3 H3 0.9300 . ?
C11 C9 1.499(8) . ?
C13 H13 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.504(9) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
Br1 C2 C3 C4 -179.8(5) . . . . ?
S12 C11 C9 N8 -178.2(5) . . . . ?
S12 C11 C9 O10 2.0(8) . . . . ?
O18 C16 C15 N14 -4.2(7) . . . . ?
O18 C16 C15 C11 175.1(6) . . . . ?
O17 C16 C15 N14 175.9(6) . . . . ?
O17 C16 C15 C11 -4.7(10) . . . . ?
N8 C5 C6 C7 -179.7(6) . . . . ?
N8 C5 C4 C3 179.7(6) . . . . ?
N14 C15 C11 S12 0.9(7) . . . . ?
N14 C15 C11 C9 179.1(7) . . . . ?
C5 N8 C9 O10 2.4(11) . . . . ?
C5 N8 C9 C11 -177.4(5) . . . . ?
C5 C6 C7 C2 1.1(9) . . . . ?
C5 C4 C3 C2 -0.8(10) . . . . ?
C6 C5 C4 C3 1.2(9) . . . . ?
C6 C7 C2 Br1 179.7(5) . . . . ?
C6 C7 C2 C3 -0.7(9) . . . . ?
C7 C2 C3 C4 0.6(10) . . . . ?
C16 O18 C19 C20 -178.7(5) . . . . ?
C16 C15 C11 S12 -178.5(5) . . . . ?
C16 C15 C11 C9 -0.3(12) . . . . ?
C15 N14 C13 S12 -0.3(7) . . . . ?
C15 C11 C9 N8 3.6(11) . . . . ?
C15 C11 C9 O10 -176.2(7) . . . . ?
C4 C5 C6 C7 -1.4(9) . . . . ?
C11 S12 C13 N14 0.7(6) . . . . ?
C9 N8 C5 C6 -4.2(9) . . . . ?
C9 N8 C5 C4 177.5(6) . . . . ?
C13 S12 C11 C15 -0.9(5) . . . . ?
C13 S12 C11 C9 -179.6(5) . . . . ?
C13 N14 C15 C16 179.1(5) . . . . ?
C13 N14 C15 C11 -0.4(8) . . . . ?
C19 O18 C16 O17 0.8(9) . . . . ?
C19 O18 C16 C15 -179.1(5) . . . . ?
