#------------------------------------------------------------------------------
#$Date: 2023-11-06 10:21:24 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287413 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/96/7159606.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_7159606
loop_
_publ_author_name
'Tiwari, Shubham'
'Chandrashekharappa, Sandeep'
'Gururaja, Guddeangadi N.'
_publ_section_title
;
 Nucleophilic sulfur controlled efficient ketothioamide synthesis from
 tribromomethyl carbinols.
;
_journal_issue                   42
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8563
_journal_page_last               8572
_journal_paper_doi               10.1039/d3ob01416a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C10 H11 N O2 S2'
_chemical_formula_sum            'C10 H11 N O2 S2'
_chemical_formula_weight         241.32
_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             2022-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-04-29 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.427(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8649(7)
_cell_length_b                   8.9005(5)
_cell_length_c                   11.3860(7)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      34.20
_cell_measurement_theta_min      2.56
_cell_volume                     1100.72(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            66766
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.451
_diffrn_reflns_theta_min         1.875
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.462
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1009 before and 0.0672 after correction. The Ratio of minimum to maximum transmission is 0.8771. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         5360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0419
_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)+(0.0422P)²+0.3530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4038
_reflns_number_total             5360
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01416a2.cif
_cod_data_source_block           gn_st_312_b_0m_a
_cod_depositor_comments          'Adding full bibliography for 7159606.cif.'
_cod_database_code               7159606
_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   0.833
_shelx_estimated_absorpt_t_min   0.805
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C8(H8)
;
_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
S1 S 0.70509(4) 0.26417(4) 0.77406(3) 0.04686(10) Uani 1 1 d . . . . .
S2 S 0.64226(3) 0.59931(4) 0.42692(3) 0.04122(9) Uani 1 1 d . . . . .
O2 O 0.84316(10) 0.35776(11) 0.55984(9) 0.0461(2) Uani 1 1 d . . . . .
O1 O 0.93522(11) 0.96763(11) 0.65714(9) 0.0484(2) Uani 1 1 d . . . . .
N1 N 0.83617(9) 0.70637(10) 0.55161(8) 0.02942(17) Uani 1 1 d . . . . .
C1 C 0.92708(14) 0.83161(16) 0.72230(11) 0.0414(3) Uani 1 1 d . . . . .
H1A H 0.850116 0.829966 0.763664 0.050 Uiso 1 1 calc R . . . .
H1B H 0.993924 0.827536 0.780290 0.050 Uiso 1 1 calc R . . . .
C2 C 0.93354(11) 0.69600(14) 0.64318(11) 0.0345(2) Uani 1 1 d . . . . .
H2A H 1.013462 0.691689 0.607211 0.041 Uiso 1 1 calc R . . . .
H2B H 0.922884 0.605120 0.688836 0.041 Uiso 1 1 calc R . . . .
C5 C 0.75588(10) 0.59870(11) 0.52690(8) 0.02645(17) Uani 1 1 d . . . . .
C6 C 0.77067(10) 0.45224(11) 0.59399(9) 0.02934(19) Uani 1 1 d . . . . .
C7 C 0.69432(10) 0.42971(12) 0.69575(9) 0.02955(19) Uani 1 1 d . . . . .
C10 C 0.59840(15) 0.32495(18) 0.86995(12) 0.0475(3) Uani 1 1 d . . . . .
H10 H 0.571772 0.268522 0.933201 0.057 Uiso 1 1 calc R . . . .
C9 C 0.55633(14) 0.46527(19) 0.84386(12) 0.0459(3) Uani 1 1 d . . . . .
H9 H 0.497679 0.515305 0.887314 0.055 Uiso 1 1 calc R . . . .
C8 C 0.61148(12) 0.52675(15) 0.74349(11) 0.0368(2) Uani 1 1 d . . . . .
H8 H 0.593655 0.621682 0.713487 0.044 Uiso 1 1 calc R . . . .
C4 C 0.83492(16) 0.97720(14) 0.57551(14) 0.0466(3) Uani 1 1 d . . . . .
H4A H 0.838639 1.072121 0.533893 0.056 Uiso 1 1 calc R . . . .
H4B H 0.758262 0.974383 0.617347 0.056 Uiso 1 1 calc R . . . .
C3 C 0.83718(13) 0.84995(13) 0.48848(10) 0.0375(2) Uani 1 1 d . . . . .
H3A H 0.765919 0.856252 0.435677 0.045 Uiso 1 1 calc R . . . .
H3B H 0.910608 0.856826 0.442027 0.045 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'
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
C10 S1 C7 91.24(7) . . ?
C4 O1 C1 109.64(10) . . ?
C5 N1 C2 124.42(9) . . ?
C5 N1 C3 122.72(10) . . ?
C3 N1 C2 112.86(9) . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
O1 C1 C2 111.39(10) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N1 C2 C1 109.27(10) . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N1 C5 S2 128.31(8) . . ?
N1 C5 C6 117.05(9) . . ?
C6 C5 S2 114.59(7) . . ?
O2 C6 C5 119.46(10) . . ?
O2 C6 C7 122.89(10) . . ?
C7 C6 C5 117.63(9) . . ?
C6 C7 S1 119.77(8) . . ?
C8 C7 S1 111.74(8) . . ?
C8 C7 C6 128.48(10) . . ?
S1 C10 H10 123.8 . . ?
C9 C10 S1 112.49(10) . . ?
C9 C10 H10 123.8 . . ?
C10 C9 H9 123.7 . . ?
C10 C9 C8 112.65(13) . . ?
C8 C9 H9 123.7 . . ?
C7 C8 C9 111.88(12) . . ?
C7 C8 H8 124.1 . . ?
C9 C8 H8 124.1 . . ?
O1 C4 H4A 109.4 . . ?
O1 C4 H4B 109.4 . . ?
O1 C4 C3 111.19(12) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
N1 C3 C4 109.42(10) . . ?
N1 C3 H3A 109.8 . . ?
N1 C3 H3B 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
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 1.7246(11) . ?
S1 C10 1.7004(16) . ?
S2 C5 1.6583(11) . ?
O2 C6 1.2222(14) . ?
O1 C1 1.4238(17) . ?
O1 C4 1.4171(19) . ?
N1 C2 1.4696(14) . ?
N1 C5 1.3215(13) . ?
N1 C3 1.4664(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.5088(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C6 1.5174(14) . ?
C6 C7 1.4556(15) . ?
C7 C8 1.3696(17) . ?
C10 H10 0.9300 . ?
C10 C9 1.360(2) . ?
C9 H9 0.9300 . ?
C9 C8 1.4137(18) . ?
C8 H8 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.5055(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
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
S1 C7 C8 C9 -0.31(14) . . . . ?
S1 C10 C9 C8 -0.06(17) . . . . ?
S2 C5 C6 O2 93.90(12) . . . . ?
S2 C5 C6 C7 -84.63(11) . . . . ?
O2 C6 C7 S1 0.43(16) . . . . ?
O2 C6 C7 C8 179.01(13) . . . . ?
O1 C1 C2 N1 -56.09(14) . . . . ?
O1 C4 C3 N1 56.99(15) . . . . ?
N1 C5 C6 O2 -83.77(14) . . . . ?
N1 C5 C6 C7 97.71(12) . . . . ?
C1 O1 C4 C3 -61.73(15) . . . . ?
C2 N1 C5 S2 179.37(9) . . . . ?
C2 N1 C5 C6 -3.34(15) . . . . ?
C2 N1 C3 C4 -52.79(15) . . . . ?
C5 N1 C2 C1 -128.10(11) . . . . ?
C5 N1 C3 C4 127.63(12) . . . . ?
C5 C6 C7 S1 178.90(8) . . . . ?
C5 C6 C7 C8 -2.51(18) . . . . ?
C6 C7 C8 C9 -178.99(12) . . . . ?
C7 S1 C10 C9 -0.10(12) . . . . ?
C10 S1 C7 C6 179.04(10) . . . . ?
C10 S1 C7 C8 0.23(10) . . . . ?
C10 C9 C8 C7 0.24(18) . . . . ?
C4 O1 C1 C2 61.42(15) . . . . ?
C3 N1 C2 C1 52.33(13) . . . . ?
C3 N1 C5 S2 -1.10(16) . . . . ?
C3 N1 C5 C6 176.19(10) . . . . ?
