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#$Date: 2024-07-05 20:56:39 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293252 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159959.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_7159959
loop_
_publ_author_name
'Jain, Anshul'
'Yadav, Vinay K.'
'Kumari, Akanksha'
'Saha, Suman K.'
'Metre, Ramesh K.'
'Bhattacharyya, Sudipta'
'Rana, Nirmal K.'
_publ_section_title
;
 Supported-amine-catalyzed cascade synthesis of
 spiro-thiazolone-tetrahydrothiophenes: assessing HSA binding activity.
;
_journal_issue                   25
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5087
_journal_page_last               5092
_journal_paper_doi               10.1039/d4ob00619d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C20 H16 Br N O3 S2'
_chemical_formula_sum            'C20 H16 Br N O3 S2'
_chemical_formula_weight         462.37
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r1)
;
_audit_update_record
;
2022-06-11 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.9260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0219(3)
_cell_length_b                   7.5128(2)
_cell_length_c                   19.5632(5)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      2.22
_cell_measurement_theta_min      28.29
_cell_volume                     1924.93(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_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_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            30510
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.307
_diffrn_reflns_theta_min         2.932
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.373
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0872 before and 0.0611 after correction. The Ratio of minimum to maximum transmission is 0.7400. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       Needle
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0287
_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)+(0.0346P)²+1.0592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4269
_reflns_number_total             4772
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00619d2.cif
_cod_data_source_block           22aprb_0m
_cod_depositor_comments          'Adding full bibliography for 7159959.cif.'
_cod_database_code               7159959
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.83593(2) -0.01408(3) 0.79265(2) 0.02404(7) Uani 1 1 d . . . . .
S1 S 0.81291(3) 0.39409(5) 0.47566(2) 0.01069(9) Uani 1 1 d . . . . .
O1 O 0.56824(9) 0.11702(16) 0.41210(7) 0.0145(2) Uani 1 1 d . . . . .
N1 N 0.72943(10) 0.10081(18) 0.40609(8) 0.0112(3) Uani 1 1 d . . . . .
C1 C 0.77557(13) 0.3812(2) 0.63532(9) 0.0142(3) Uani 1 1 d . . . . .
H1 H 0.807268 0.484594 0.628206 0.017 Uiso 1 1 calc R . . . .
S2 S 0.64472(3) 0.66709(5) 0.51866(2) 0.01371(9) Uani 1 1 d . . . . .
O2 O 0.51843(9) 0.48852(15) 0.35770(7) 0.0124(2) Uani 1 1 d . . . . .
C2 C 0.81997(13) 0.2821(2) 0.69876(10) 0.0162(3) Uani 1 1 d . . . . .
H2 H 0.881236 0.318078 0.734100 0.019 Uiso 1 1 calc R . . . .
O3 O 0.53882(11) 0.3357(2) 0.26455(8) 0.0267(3) Uani 1 1 d . . . . .
C3 C 0.77139(14) 0.1285(2) 0.70850(9) 0.0162(3) Uani 1 1 d . . . . .
C4 C 0.67905(14) 0.0738(3) 0.65780(10) 0.0171(3) Uani 1 1 d . . . . .
H4 H 0.646731 -0.027927 0.665812 0.021 Uiso 1 1 calc R . . . .
C5 C 0.63560(13) 0.1743(2) 0.59453(10) 0.0148(3) Uani 1 1 d . . . . .
H5 H 0.573457 0.139298 0.559968 0.018 Uiso 1 1 calc R . . . .
C6 C 0.68371(12) 0.3268(2) 0.58214(9) 0.0115(3) Uani 1 1 d . . . . .
C7 C 0.63459(12) 0.4239(2) 0.51052(9) 0.0101(3) Uani 1 1 d . . . . .
H7 H 0.561738 0.394222 0.492403 0.012 Uiso 1 1 calc R . . . .
C8 C 0.67529(12) 0.3780(2) 0.44950(9) 0.0092(3) Uani 1 1 d . . . . .
C9 C 0.62652(13) 0.5180(2) 0.38866(10) 0.0119(3) Uani 1 1 d . . . . .
H9 H 0.657286 0.512778 0.350913 0.014 Uiso 1 1 calc R . . . .
C10 C 0.64302(13) 0.6992(2) 0.42541(10) 0.0156(3) Uani 1 1 d . . . . .
H10A H 0.588315 0.779643 0.398663 0.019 Uiso 1 1 calc R . . . .
H10B H 0.707250 0.749764 0.426610 0.019 Uiso 1 1 calc R . . . .
C11 C 0.48340(14) 0.4000(2) 0.29268(9) 0.0164(3) Uani 1 1 d . . . . .
C12 C 0.36996(14) 0.3980(3) 0.26342(11) 0.0236(4) Uani 1 1 d . . . . .
H12A H 0.345513 0.366252 0.301785 0.035 Uiso 1 1 calc GR . . . .
H12B H 0.346149 0.312591 0.224511 0.035 Uiso 1 1 calc GR . . . .
H12C H 0.344927 0.514046 0.245067 0.035 Uiso 1 1 calc GR . . . .
C13 C 0.64979(12) 0.1857(2) 0.42106(9) 0.0099(3) Uani 1 1 d . . . . .
C14 C 0.81326(12) 0.1915(2) 0.43042(9) 0.0101(3) Uani 1 1 d . . . . .
C15 C 0.90768(12) 0.1324(2) 0.42084(9) 0.0112(3) Uani 1 1 d . . . . .
C16 C 0.90664(14) -0.0219(2) 0.38091(10) 0.0165(4) Uani 1 1 d . . . . .
H16 H 0.847100 -0.088575 0.361751 0.020 Uiso 1 1 calc R . . . .
C17 C 0.99460(14) -0.0755(3) 0.36988(11) 0.0209(4) Uani 1 1 d . . . . .
H17 H 0.993979 -0.178563 0.343376 0.025 Uiso 1 1 calc R . . . .
C18 C 1.08386(14) 0.0239(2) 0.39824(10) 0.0169(4) Uani 1 1 d . . . . .
H18 H 1.142725 -0.012661 0.390740 0.020 Uiso 1 1 calc R . . . .
C19 C 1.08482(13) 0.1771(2) 0.43758(11) 0.0183(4) Uani 1 1 d . . . . .
H19 H 1.144359 0.243908 0.456413 0.022 Uiso 1 1 calc R . . . .
C20 C 0.99705(13) 0.2315(2) 0.44905(10) 0.0163(3) Uani 1 1 d . . . . .
H20 H 0.998033 0.334471 0.475675 0.020 Uiso 1 1 calc R . . . .
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'
Br Br -0.2901 2.4595 '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'
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
C14 S1 C8 89.67(7) . . ?
C14 N1 C13 111.71(14) . . ?
C2 C1 C6 120.55(16) . . ?
C10 S2 C7 94.11(8) . . ?
C11 O2 C9 116.35(13) . . ?
C3 C2 C1 118.89(16) . . ?
C2 C3 Br1 118.85(14) . . ?
C4 C3 Br1 119.20(14) . . ?
C4 C3 C2 121.92(17) . . ?
C3 C4 C5 118.51(17) . . ?
C4 C5 C6 121.03(17) . . ?
C1 C6 C7 122.90(15) . . ?
C5 C6 C1 119.06(16) . . ?
C5 C6 C7 118.03(15) . . ?
C6 C7 S2 113.91(11) . . ?
C6 C7 C8 116.08(13) . . ?
C8 C7 S2 104.64(11) . . ?
C7 C8 S1 114.76(11) . . ?
C7 C8 C9 105.05(13) . . ?
C7 C8 C13 112.85(13) . . ?
C9 C8 S1 107.68(11) . . ?
C13 C8 S1 104.48(10) . . ?
C13 C8 C9 112.08(13) . . ?
O2 C9 C8 109.20(13) . . ?
O2 C9 C10 107.32(13) . . ?
C10 C9 C8 107.07(14) . . ?
C9 C10 S2 107.41(12) . . ?
O2 C11 C12 110.11(15) . . ?
O3 C11 O2 123.18(17) . . ?
O3 C11 C12 126.70(17) . . ?
O1 C13 N1 123.87(15) . . ?
O1 C13 C8 122.48(14) . . ?
N1 C13 C8 113.65(13) . . ?
N1 C14 S1 118.34(12) . . ?
N1 C14 C15 122.39(15) . . ?
C15 C14 S1 119.27(12) . . ?
C16 C15 C14 119.49(15) . . ?
C20 C15 C14 120.84(15) . . ?
C20 C15 C16 119.64(15) . . ?
C17 C16 C15 119.80(17) . . ?
C16 C17 C18 120.38(17) . . ?
C19 C18 C17 119.85(16) . . ?
C18 C19 C20 120.13(16) . . ?
C19 C20 C15 120.21(16) . . ?
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 C3 1.9007(18) . ?
S1 C8 1.8152(16) . ?
S1 C14 1.7617(16) . ?
O1 C13 1.209(2) . ?
N1 C13 1.405(2) . ?
N1 C14 1.293(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.397(2) . ?
S2 C7 1.8348(17) . ?
S2 C10 1.8317(19) . ?
O2 C9 1.434(2) . ?
O2 C11 1.362(2) . ?
C2 C3 1.387(3) . ?
O3 C11 1.202(2) . ?
C3 C4 1.383(3) . ?
C4 C5 1.391(2) . ?
C5 C6 1.394(2) . ?
C6 C7 1.510(2) . ?
C7 C8 1.535(2) . ?
C8 C9 1.552(2) . ?
C8 C13 1.543(2) . ?
C9 C10 1.518(2) . ?
C11 C12 1.486(3) . ?
C14 C15 1.470(2) . ?
C15 C16 1.395(2) . ?
C15 C20 1.391(2) . ?
C16 C17 1.386(2) . ?
C17 C18 1.391(3) . ?
C18 C19 1.382(3) . ?
C19 C20 1.389(2) . ?
