#------------------------------------------------------------------------------
#$Date: 2022-03-23 03:33:21 +0200 (Wed, 23 Mar 2022) $
#$Revision: 273909 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158583.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_7158583
loop_
_publ_author_name
'Jain, Anshul'
'Maji, Sushobhan'
'Shukla, Khyati'
'Kumari, Akanksha'
'Garg, Shivani'
'Metre, Ramesh K.'
'Bhattacharyya, Sudipta'
'Rana, Nirmal K.'
_publ_section_title
;
 Stereoselective synthesis of tri-substituted tetrahydrothiophenes and
 their in silico binding against mycobacterial protein tyrosine
 phosphatase B
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00052K
_journal_year                    2022
_chemical_formula_moiety         'C12 H14 O5 S'
_chemical_formula_sum            'C12 H14 O5 S'
_chemical_formula_weight         270.29
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-04 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                73.419(3)
_cell_angle_beta                 75.274(4)
_cell_angle_gamma                72.063(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8434(7)
_cell_length_b                   10.0084(8)
_cell_length_c                   10.5726(9)
_cell_measurement_reflns_used    3986
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.698
_cell_measurement_theta_min      3.320
_cell_volume                     649.21(10)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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      100
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.955
_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  0.0929
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17407
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_min         3.320
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1197 before and 0.0876 after correction.
The Ratio of minimum to maximum transmission is 0.7599.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.385
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.385
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0735
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1965
_refine_ls_wR_factor_ref         0.2237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2209
_reflns_number_total             3211
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00052k2.cif
_cod_data_source_block           tr1
_cod_database_code               7158583
_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   0.980
_shelx_estimated_absorpt_t_min   0.961
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
S1 S 0.70620(12) 0.30015(7) 0.26375(8) 0.0780(4) Uani 1 1 d . . . . .
O1 O 0.7069(3) 0.57551(17) 0.02002(15) 0.0566(5) Uani 1 1 d . . . . .
H1 H 0.716905 0.491826 0.013600 0.085 Uiso 1 1 calc GR . . . .
O2 O 0.1934(3) 0.66144(19) 0.1183(2) 0.0712(6) Uani 1 1 d . . . . .
O3 O 0.2782(5) 0.4426(3) 0.4928(2) 0.1095(10) Uani 1 1 d . . . . .
O4 O 0.2415(4) 0.2755(2) 0.4084(2) 0.0762(6) Uani 1 1 d . . . . .
O5 O 0.1671(4) 0.9436(2) 0.0850(2) 0.0899(7) Uani 1 1 d . . . . .
C1 C 0.4477(3) 0.4255(2) 0.2679(2) 0.0433(5) Uani 1 1 d . . . . .
H1A H 0.382353 0.419012 0.196074 0.052 Uiso 1 1 calc R . . . .
C2 C 0.4788(3) 0.5768(2) 0.2391(2) 0.0411(4) Uani 1 1 d . . . . .
H2 H 0.471884 0.599871 0.326328 0.049 Uiso 1 1 calc R . . . .
C3 C 0.6995(3) 0.5747(2) 0.1549(2) 0.0467(5) Uani 1 1 d . . . . .
H3 H 0.740437 0.661216 0.157956 0.056 Uiso 1 1 calc R . . . .
C4 C 0.8415(4) 0.4391(3) 0.2261(3) 0.0626(7) Uani 1 1 d . . . . .
H4A H 0.864191 0.453714 0.309557 0.075 Uiso 1 1 calc R . . . .
H4B H 0.978628 0.413552 0.167223 0.075 Uiso 1 1 calc R . . . .
C5 C 0.3128(3) 0.6911(2) 0.1677(2) 0.0470(5) Uani 1 1 d . . . . .
C6 C 0.3009(4) 0.8408(2) 0.1580(2) 0.0558(6) Uani 1 1 d . . . . .
C7 C 0.4078(6) 0.8959(3) 0.2136(4) 0.0817(9) Uani 1 1 d . . . . .
H7 H 0.509728 0.847144 0.268918 0.098 Uiso 1 1 calc R . . . .
C8 C 0.3221(9) 1.0540(4) 0.1644(6) 0.1115(16) Uani 1 1 d . . . . .
H8 H 0.360268 1.128847 0.183458 0.134 Uiso 1 1 calc R . . . .
C9 C 0.1911(9) 1.0706(4) 0.0936(5) 0.1145(16) Uani 1 1 d . . . . .
H9 H 0.116270 1.162271 0.050371 0.137 Uiso 1 1 calc R . . . .
C10 C 0.3143(4) 0.3849(3) 0.4026(2) 0.0516(5) Uani 1 1 d . . . . .
C11 C 0.1129(6) 0.2185(4) 0.5351(4) 0.0945(11) Uani 1 1 d . . . . .
H11A H 0.123318 0.260153 0.606900 0.113 Uiso 1 1 calc R . . . .
H11B H -0.035114 0.248247 0.524629 0.113 Uiso 1 1 calc R . . . .
C12 C 0.1733(13) 0.0761(6) 0.5708(8) 0.243(5) Uani 1 1 d . . . . .
H12A H 0.313046 0.042058 0.520177 0.364 Uiso 1 1 calc GR . . . .
H12B H 0.074751 0.034560 0.551591 0.364 Uiso 1 1 calc GR . . . .
H12C H 0.176841 0.046424 0.667095 0.364 Uiso 1 1 calc GR . . . .
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'
Cl Cl 0.1484 0.1585 '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
C4 S1 C1 94.29(10) . . ?
C10 O4 C11 118.2(3) . . ?
C6 O5 C9 105.0(3) . . ?
C2 C1 S1 107.03(14) . . ?
C10 C1 S1 108.94(14) . . ?
C10 C1 C2 113.02(17) . . ?
C1 C2 C3 107.70(16) . . ?
C5 C2 C1 112.46(16) . . ?
C5 C2 C3 111.19(17) . . ?
O1 C3 C2 111.44(17) . . ?
O1 C3 C4 113.05(18) . . ?
C4 C3 C2 104.73(18) . . ?
C3 C4 S1 105.30(16) . . ?
O2 C5 C2 122.69(18) . . ?
O2 C5 C6 119.8(2) . . ?
C6 C5 C2 117.52(19) . . ?
O5 C6 C5 118.2(2) . . ?
O5 C6 C7 112.8(2) . . ?
C7 C6 C5 128.9(2) . . ?
C6 C7 C8 101.3(4) . . ?
C9 C8 C7 108.0(3) . . ?
C8 C9 O5 113.0(3) . . ?
O3 C10 O4 123.7(2) . . ?
O3 C10 C1 125.2(2) . . ?
O4 C10 C1 111.04(19) . . ?
C12 C11 O4 111.6(4) . . ?
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 C1 1.825(2) . ?
S1 C4 1.800(3) . ?
O1 C3 1.412(3) . ?
O2 C5 1.217(3) . ?
O3 C10 1.188(3) . ?
O4 C10 1.316(3) . ?
O4 C11 1.473(4) . ?
O5 C6 1.349(3) . ?
O5 C9 1.362(6) . ?
C1 C2 1.527(3) . ?
C1 C10 1.504(3) . ?
C2 C3 1.543(3) . ?
C2 C5 1.521(3) . ?
C3 C4 1.526(3) . ?
C5 C6 1.451(3) . ?
C6 C7 1.355(4) . ?
C7 C8 1.494(6) . ?
C8 C9 1.254(7) . ?
C11 C12 1.324(6) . ?
