#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:05:18 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299104 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160303.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_7160303
loop_
_publ_author_name
'Duari, Surajit'
'Maity, Srabani'
'Biswas, Subrata'
'Roy, Arnab'
'Elsharif, Asma M.'
'Biswas, Srijit'
_publ_section_title
;
 H₃PO₃ promoted reactions of thioamides with
 2-substituted benzyl alcohols.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1418
_journal_page_last               1424
_journal_paper_doi               10.1039/d4ob01560f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C15 H14 O3 S'
_chemical_formula_sum            'C15 H14 O3 S'
_chemical_formula_weight         274.32
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-07-12 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.395(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.4993(14)
_cell_length_b                   15.165(4)
_cell_length_c                   19.844(6)
_cell_measurement_reflns_used    6115
_cell_measurement_temperature    189.68
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.46
_cell_volume                     1345.6(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      189.68
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.988
_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  0.0433
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15607
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.073
_diffrn_reflns_theta_min         2.464
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6197
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1310 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.8313.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.012(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0411
_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)+(0.0300P)²+0.5124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2428
_reflns_number_total             2926
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01560f2.cif
_cod_data_source_block           p3149
_cod_depositor_comments          'Adding full bibliography for 7160303.cif.'
_cod_database_code               7160303
_shelx_shelxl_version_number     2016/6
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.39379(12) 0.44995(3) 0.32569(2) 0.05279(19) Uani 1 1 d . . . . .
O1 O 0.5669(3) 0.28861(8) 0.29965(7) 0.0632(4) Uani 1 1 d . . . . .
O2 O 1.1454(3) 0.29226(10) 0.60614(7) 0.0680(4) Uani 1 1 d . . . . .
O3 O 0.3096(3) 0.60876(8) 0.21581(6) 0.0560(3) Uani 1 1 d . . . . .
H3 H 0.347404 0.660619 0.204556 0.084 Uiso 1 1 calc R U . . .
C1 C 0.5725(4) 0.34754(10) 0.34314(8) 0.0452(4) Uani 1 1 d . . . . .
C2 C 0.7265(4) 0.33831(10) 0.41257(8) 0.0431(4) Uani 1 1 d . . . . .
C3 C 0.9243(4) 0.26877(12) 0.42716(9) 0.0526(4) Uani 1 1 d . . . . .
H3A H 0.964738 0.229647 0.391914 0.063 Uiso 1 1 calc R U . . .
C4 C 1.0621(4) 0.25564(13) 0.49145(10) 0.0590(5) Uani 1 1 d . . . . .
H4 H 1.197863 0.207959 0.500234 0.071 Uiso 1 1 calc R U . . .
C5 C 1.0047(4) 0.31160(11) 0.54395(9) 0.0490(4) Uani 1 1 d . . . . .
C6 C 0.8084(5) 0.38074(13) 0.53032(10) 0.0677(6) Uani 1 1 d . . . . .
H6 H 0.765967 0.419398 0.565689 0.081 Uiso 1 1 calc R U . . .
C7 C 0.6741(5) 0.39358(13) 0.46536(10) 0.0685(6) Uani 1 1 d . . . . .
H7 H 0.541161 0.441923 0.456493 0.082 Uiso 1 1 calc R U . . .
C8 C 1.0529(6) 0.33679(16) 0.66342(10) 0.0728(6) Uani 1 1 d . . . . .
H8A H 0.835586 0.331525 0.662914 0.109 Uiso 1 1 calc R U . . .
H8B H 1.107801 0.399220 0.661705 0.109 Uiso 1 1 calc R U . . .
H8C H 1.151659 0.310274 0.705070 0.109 Uiso 1 1 calc R U . . .
C9 C 0.2065(4) 0.43297(11) 0.24053(9) 0.0507(4) Uani 1 1 d . . . . .
H9A H 0.157416 0.369607 0.234561 0.061 Uiso 1 1 calc R U . . .
H9B H 0.015883 0.466200 0.235811 0.061 Uiso 1 1 calc R U . . .
C10 C 0.3884(4) 0.46125(10) 0.18530(8) 0.0422(4) Uani 1 1 d . . . . .
C11 C 0.4312(4) 0.55087(11) 0.17389(8) 0.0432(4) Uani 1 1 d . . . . .
C12 C 0.5901(4) 0.57855(13) 0.12168(9) 0.0546(5) Uani 1 1 d . . . . .
H12 H 0.617084 0.639698 0.113944 0.065 Uiso 1 1 calc R U . . .
C13 C 0.7083(5) 0.51714(16) 0.08119(10) 0.0656(5) Uani 1 1 d . . . . .
H13 H 0.818392 0.536148 0.045693 0.079 Uiso 1 1 calc R U . . .
C14 C 0.6684(5) 0.42803(16) 0.09167(10) 0.0672(6) Uani 1 1 d . . . . .
H14 H 0.749786 0.385833 0.063465 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5091(4) 0.40097(12) 0.14355(10) 0.0550(5) Uani 1 1 d . . . . .
H15 H 0.481800 0.339707 0.150750 0.066 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 0.0033 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'
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
C1 S1 C9 102.20(8) . . ?
C5 O2 C8 118.43(15) . . ?
C11 O3 H3 109.5 . . ?
O1 C1 S1 121.58(13) . . ?
O1 C1 C2 123.46(15) . . ?
C2 C1 S1 114.96(12) . . ?
C3 C2 C1 119.27(15) . . ?
C7 C2 C1 123.17(15) . . ?
C7 C2 C3 117.50(16) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 C2 121.16(16) . . ?
C4 C3 H3A 119.4 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.45(16) . . ?
C5 C4 H4 119.8 . . ?
O2 C5 C4 116.33(15) . . ?
O2 C5 C6 124.58(16) . . ?
C6 C5 C4 119.08(17) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.78(17) . . ?
C7 C6 H6 120.1 . . ?
C2 C7 H7 119.0 . . ?
C6 C7 C2 122.02(17) . . ?
C6 C7 H7 119.0 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
S1 C9 H9A 108.8 . . ?
S1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 S1 113.79(12) . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C11 C10 C9 119.56(15) . . ?
C15 C10 C9 122.02(16) . . ?
C15 C10 C11 118.39(16) . . ?
O3 C11 C10 117.11(15) . . ?
O3 C11 C12 122.35(15) . . ?
C12 C11 C10 120.54(16) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.76(18) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.61(19) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.32(19) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.38(18) . . ?
C14 C15 H15 119.3 . . ?
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 1.7654(17) . ?
S1 C9 1.8208(19) . ?
O1 C1 1.241(2) . ?
O2 C5 1.355(2) . ?
O2 C8 1.424(2) . ?
O3 H3 0.8400 . ?
O3 C11 1.365(2) . ?
C1 C2 1.478(2) . ?
C2 C3 1.390(2) . ?
C2 C7 1.382(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.370(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 C6 1.378(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.375(3) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.502(2) . ?
C10 C11 1.395(2) . ?
C10 C15 1.385(2) . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9500 . ?
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 C1 C2 C3 -166.63(14) . . . . ?
S1 C1 C2 C7 16.3(2) . . . . ?
S1 C9 C10 C11 -72.14(18) . . . . ?
S1 C9 C10 C15 109.81(16) . . . . ?
O1 C1 C2 C3 13.3(3) . . . . ?
O1 C1 C2 C7 -163.7(2) . . . . ?
O2 C5 C6 C7 -179.0(2) . . . . ?
O3 C11 C12 C13 179.79(17) . . . . ?
C1 S1 C9 C10 -92.30(14) . . . . ?
C1 C2 C3 C4 -177.24(18) . . . . ?
C1 C2 C7 C6 176.5(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
C3 C4 C5 O2 178.42(18) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C2 0.8(4) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C8 O2 C5 C4 -168.41(19) . . . . ?
C8 O2 C5 C6 10.2(3) . . . . ?
C9 S1 C1 O1 4.91(17) . . . . ?
C9 S1 C1 C2 -175.15(13) . . . . ?
C9 C10 C11 O3 1.9(2) . . . . ?
C9 C10 C11 C12 -177.85(15) . . . . ?
C9 C10 C15 C14 178.04(17) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C10 0.0(3) . . . . ?
C15 C10 C11 O3 179.99(14) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?
