#------------------------------------------------------------------------------
#$Date: 2022-03-23 03:33:21 +0200 (Wed, 23 Mar 2022) $
#$Revision: 273909 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158584.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_7158584
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         'C17 H20 O6 S'
_chemical_formula_sum            'C17 H20 O6 S'
_chemical_formula_weight         352.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   41.990(11)
_cell_length_b                   7.821(2)
_cell_length_c                   10.606(3)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.475
_cell_measurement_theta_min      2.911
_cell_volume                     3483.1(16)
_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      100
_diffrn_measured_fraction_theta_full 0.896
_diffrn_measured_fraction_theta_max 0.907
_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  0.1118
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.896
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            38806
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.475
_diffrn_reflns_theta_min         2.911
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1325 before and 0.0823 after correction.
The Ratio of minimum to maximum transmission is 0.6873.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.958
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.292
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.292
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0795
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1819
_refine_ls_wR_factor_ref         0.2053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2941
_reflns_number_total             4006
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00052k2.cif
_cod_data_source_block           14decb
_cod_original_cell_volume        3483.0(16)
_cod_database_code               7158584
_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   0.983
_shelx_estimated_absorpt_t_min   0.983
_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:
 C2(H2), C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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 0.45255(2) 0.12562(10) 0.49265(7) 0.0343(2) Uani 1 1 d . . . . .
O1 O 0.42412(5) 0.5658(3) 0.4753(2) 0.0463(6) Uani 1 1 d . . . . .
O2 O 0.46648(4) 0.4729(3) 0.36455(17) 0.0317(5) Uani 1 1 d . . . . .
O3 O 0.38908(5) -0.0302(3) 0.35906(17) 0.0345(5) Uani 1 1 d . . . . .
O4 O 0.33899(6) -0.1010(6) 0.3826(3) 0.1178(18) Uani 1 1 d . . . . .
O5 O 0.37291(4) 0.3522(3) 0.26685(16) 0.0359(6) Uani 1 1 d . . . . .
O6 O 0.24745(5) 0.4966(3) 0.58515(17) 0.0390(6) Uani 1 1 d . . . . .
C1 C 0.41950(6) -0.0067(4) 0.5494(2) 0.0296(6) Uani 1 1 d . . . . .
H1A H 0.423620 -0.128793 0.531047 0.036 Uiso 1 1 calc R . . . .
H1B H 0.416886 0.007030 0.641650 0.036 Uiso 1 1 calc R . . . .
C2 C 0.38959(6) 0.0536(4) 0.4807(2) 0.0278(6) Uani 1 1 d . . . . .
H2 H 0.369980 0.026351 0.530277 0.033 Uiso 1 1 calc R . . . .
C3 C 0.39310(6) 0.2460(4) 0.4613(2) 0.0252(6) Uani 1 1 d . . . . .
H3 H 0.392351 0.302595 0.545761 0.030 Uiso 1 1 calc R . . . .
C4 C 0.42643(6) 0.2727(4) 0.4059(2) 0.0253(6) Uani 1 1 d . . . . .
H4 H 0.426318 0.241092 0.314540 0.030 Uiso 1 1 calc R . . . .
C5 C 0.36725(6) 0.3251(4) 0.3788(2) 0.0265(6) Uani 1 1 d . . . . .
C6 C 0.33557(6) 0.3658(4) 0.4329(2) 0.0257(6) Uani 1 1 d . . . . .
C7 C 0.32906(6) 0.3559(4) 0.5628(2) 0.0305(7) Uani 1 1 d . . . . .
H7 H 0.345211 0.318331 0.619034 0.037 Uiso 1 1 calc R . . . .
C8 C 0.29961(6) 0.3997(4) 0.6094(2) 0.0344(7) Uani 1 1 d . . . . .
H8 H 0.295720 0.393210 0.697474 0.041 Uiso 1 1 calc R . . . .
C9 C 0.27539(6) 0.4537(4) 0.5286(2) 0.0312(6) Uani 1 1 d . . . . .
C10 C 0.28104(6) 0.4628(4) 0.3988(2) 0.0322(7) Uani 1 1 d . . . . .
H10 H 0.264597 0.496703 0.342565 0.039 Uiso 1 1 calc R . . . .
C11 C 0.31124(6) 0.4211(4) 0.3533(2) 0.0306(6) Uani 1 1 d . . . . .
H11 H 0.315346 0.430757 0.265460 0.037 Uiso 1 1 calc R . . . .
C12 C 0.22100(7) 0.5433(5) 0.5054(3) 0.0395(7) Uani 1 1 d . . . . .
H12A H 0.227059 0.640571 0.452302 0.059 Uiso 1 1 calc GR . . . .
H12B H 0.202729 0.574979 0.557891 0.059 Uiso 1 1 calc GR . . . .
H12C H 0.215259 0.445996 0.451776 0.059 Uiso 1 1 calc GR . . . .
C13 C 0.43821(6) 0.4541(4) 0.4205(2) 0.0267(6) Uani 1 1 d . . . . .
C14 C 0.48147(7) 0.6411(4) 0.3717(2) 0.0340(7) Uani 1 1 d . . . . .
H14A H 0.504890 0.627771 0.366998 0.041 Uiso 1 1 calc R . . . .
H14B H 0.476251 0.694625 0.453706 0.041 Uiso 1 1 calc R . . . .
C15 C 0.47040(8) 0.7560(5) 0.2662(3) 0.0446(8) Uani 1 1 d . . . . .
H15A H 0.475010 0.701761 0.184912 0.067 Uiso 1 1 calc GR . . . .
H15B H 0.481578 0.865811 0.271273 0.067 Uiso 1 1 calc GR . . . .
H15C H 0.447414 0.775183 0.273791 0.067 Uiso 1 1 calc GR . . . .
C16 C 0.36257(7) -0.1103(5) 0.3243(3) 0.0374(8) Uani 1 1 d . . . . .
C17 C 0.36639(7) -0.2069(4) 0.2034(3) 0.0361(7) Uani 1 1 d . . . . .
H17A H 0.383053 -0.153079 0.152305 0.054 Uiso 1 1 calc GR . . . .
H17B H 0.346229 -0.205469 0.156854 0.054 Uiso 1 1 calc GR . . . .
H17C H 0.372381 -0.325367 0.221898 0.054 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
C1 S1 C4 93.79(12) . . ?
C13 O2 C14 117.4(2) . . ?
C16 O3 C2 118.2(2) . . ?
C9 O6 C12 117.9(2) . . ?
C2 C1 S1 106.96(19) . . ?
O3 C2 C1 107.3(2) . . ?
O3 C2 C3 109.1(2) . . ?
C3 C2 C1 106.8(2) . . ?
C2 C3 C4 105.9(2) . . ?
C5 C3 C2 114.1(2) . . ?
C5 C3 C4 112.0(2) . . ?
C3 C4 S1 105.55(18) . . ?
C13 C4 S1 109.96(17) . . ?
C13 C4 C3 112.8(2) . . ?
O5 C5 C3 119.1(2) . . ?
O5 C5 C6 120.7(2) . . ?
C6 C5 C3 120.2(2) . . ?
C7 C6 C5 122.8(2) . . ?
C11 C6 C5 119.3(2) . . ?
C11 C6 C7 117.9(2) . . ?
C8 C7 C6 120.9(2) . . ?
C7 C8 C9 120.7(2) . . ?
O6 C9 C8 115.6(2) . . ?
O6 C9 C10 124.6(2) . . ?
C8 C9 C10 119.7(2) . . ?
C11 C10 C9 118.9(2) . . ?
C6 C11 C10 121.9(2) . . ?
O1 C13 O2 124.8(3) . . ?
O1 C13 C4 124.8(2) . . ?
O2 C13 C4 110.4(2) . . ?
O2 C14 C15 111.4(2) . . ?
O3 C16 C17 112.7(2) . . ?
O4 C16 O3 122.2(3) . . ?
O4 C16 C17 125.1(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 C1 1.833(3) . ?
S1 C4 1.837(3) . ?
O1 C13 1.205(3) . ?
O2 C13 1.335(3) . ?
O2 C14 1.460(3) . ?
O3 C2 1.447(3) . ?
O3 C16 1.329(3) . ?
O4 C16 1.170(4) . ?
O5 C5 1.229(3) . ?
O6 C9 1.360(3) . ?
O6 C12 1.443(3) . ?
C1 C2 1.527(4) . ?
C2 C3 1.526(4) . ?
C3 C4 1.532(3) . ?
C3 C5 1.525(3) . ?
C4 C13 1.510(4) . ?
C5 C6 1.483(3) . ?
C6 C7 1.406(3) . ?
C6 C11 1.395(3) . ?
C7 C8 1.375(4) . ?
C8 C9 1.395(4) . ?
C9 C10 1.399(3) . ?
C10 C11 1.395(4) . ?
C14 C15 1.509(4) . ?
C16 C17 1.497(4) . ?
