#------------------------------------------------------------------------------
#$Date: 2021-12-07 05:53:52 +0200 (Tue, 07 Dec 2021) $
#$Revision: 271224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158399.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_7158399
loop_
_publ_author_name
'Khan, Tabassum'
'Rajesh, Pallava'
'Arun, Doma'
'Yaragorla, Srinivasarao'
_publ_section_title
;
 Stereoselective sulfenylation of oxindole-derived propargyl alcohols to
 access sulfenylated-3-alkenyloxindoles.
;
_journal_issue                   46
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              10201
_journal_page_last               10209
_journal_paper_doi               10.1039/d1ob01921j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C22 H17 N O S'
_chemical_formula_sum            'C22 H17 N O S'
_chemical_formula_weight         343.42
_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
_audit_creation_date             2021-09-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-15 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                115.159(12)
_cell_angle_beta                 102.060(13)
_cell_angle_gamma                95.668(13)
_cell_formula_units_Z            2
_cell_length_a                   7.472(2)
_cell_length_b                   10.980(3)
_cell_length_c                   12.170(4)
_cell_measurement_reflns_used    3248
_cell_measurement_temperature    298.22
_cell_measurement_theta_max      23.96
_cell_measurement_theta_min      2.85
_cell_volume                     863.7(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.22
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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  0.2059
_diffrn_reflns_av_unetI/netI     0.1347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.750
_diffrn_reflns_theta_min         2.852
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1666 before and 0.0789 after correction.
The Ratio of minimum to maximum transmission is 0.8944.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1915
_refine_ls_R_factor_gt           0.0779
_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)+(0.0309P)²+0.7274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1946
_reflns_number_total             4034
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01921j2.cif
_cod_data_source_block           ysr32a_0m_a
_cod_depositor_comments          'Adding full bibliography for 7158399.cif.'
_cod_database_code               7158399
_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   0.977
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C16(H16), C2(H2), C14(H14), C15(H15), C18(H18), C3(H3),
 C22(H22), C6(H6), C4(H4), C19(H19), C20(H20), C21(H21), C5(H5)
;
_olex2_submission_original_sample_id SYTK-SPh-1
_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 0.91136(16) 0.53267(11) 0.29576(11) 0.0821(5) Uani 1 1 d . . . . .
O1 O 0.4694(3) 0.8213(2) 0.3835(2) 0.0523(7) Uani 1 1 d . . . . .
N1 N 0.7233(4) 0.9558(3) 0.5508(2) 0.0456(8) Uani 1 1 d . . . . .
H1 H 0.672655 1.024066 0.585931 0.055 Uiso 1 1 calc R . . . .
C10 C 0.6327(5) 0.8398(3) 0.4428(3) 0.0414(8) Uani 1 1 d . . . . .
C1 C 0.4305(4) 0.4447(3) 0.2104(3) 0.0428(9) Uani 1 1 d . . . . .
C9 C 0.7684(4) 0.7480(3) 0.4159(3) 0.0384(8) Uani 1 1 d . . . . .
C12 C 0.9072(5) 0.9513(3) 0.5978(3) 0.0393(8) Uani 1 1 d . . . . .
C7 C 0.5493(5) 0.5645(3) 0.2107(3) 0.0438(9) Uani 1 1 d . . . . .
H7A H 0.574194 0.534286 0.129091 0.053 Uiso 1 1 calc R . . . .
H7B H 0.478849 0.636386 0.221625 0.053 Uiso 1 1 calc R . . . .
C11 C 0.9423(5) 0.8241(3) 0.5194(3) 0.0383(8) Uani 1 1 d . . . . .
C13 C 1.0416(5) 1.0509(3) 0.7019(3) 0.0486(9) Uani 1 1 d . . . . .
H13 H 1.015283 1.134525 0.752194 0.058 Uiso 1 1 calc R . . . .
C17 C 0.8256(5) 0.3874(3) 0.1470(3) 0.0479(9) Uani 1 1 d . . . . .
C16 C 1.1199(5) 0.8000(4) 0.5499(3) 0.0497(9) Uani 1 1 d . . . . .
H16 H 1.147818 0.716764 0.500059 0.060 Uiso 1 1 calc R . . . .
C8 C 0.7336(5) 0.6243(3) 0.3126(3) 0.0409(8) Uani 1 1 d . . . . .
C2 C 0.3337(5) 0.3323(4) 0.0981(4) 0.0544(10) Uani 1 1 d . . . . .
H2 H 0.342412 0.330790 0.022406 0.065 Uiso 1 1 calc R . . . .
C14 C 1.2168(5) 1.0234(4) 0.7296(3) 0.0549(10) Uani 1 1 d . . . . .
H14 H 1.309958 1.089148 0.799912 0.066 Uiso 1 1 calc R . . . .
C15 C 1.2554(5) 0.9000(4) 0.6545(3) 0.0575(10) Uani 1 1 d . . . . .
H15 H 1.374681 0.883598 0.674614 0.069 Uiso 1 1 calc R . . . .
C18 C 0.8313(6) 0.3968(5) 0.0390(4) 0.0708(12) Uani 1 1 d . . . . .
H18 H 0.872089 0.482080 0.043538 0.085 Uiso 1 1 calc R . . . .
C3 C 0.2243(5) 0.2219(4) 0.0951(5) 0.0667(12) Uani 1 1 d . . . . .
H3 H 0.161012 0.146386 0.018247 0.080 Uiso 1 1 calc R . . . .
C22 C 0.7643(5) 0.2617(4) 0.1383(4) 0.0667(12) Uani 1 1 d . . . . .
H22 H 0.759040 0.253678 0.210721 0.080 Uiso 1 1 calc R . . . .
C6 C 0.4110(6) 0.4450(5) 0.3193(4) 0.0785(14) Uani 1 1 d . . . . .
H6 H 0.472671 0.520497 0.396637 0.094 Uiso 1 1 calc R . . . .
C4 C 0.2094(6) 0.2240(5) 0.2044(5) 0.0799(14) Uani 1 1 d . . . . .
H4 H 0.136217 0.149611 0.203148 0.096 Uiso 1 1 calc R . . . .
C19 C 0.7778(8) 0.2821(7) -0.0748(4) 0.103(2) Uani 1 1 d . . . . .
H19 H 0.781752 0.289509 -0.147673 0.124 Uiso 1 1 calc R . . . .
C20 C 0.7192(7) 0.1580(7) -0.0826(6) 0.113(3) Uani 1 1 d . . . . .
H20 H 0.684751 0.079867 -0.160606 0.135 Uiso 1 1 calc R . . . .
C21 C 0.7101(6) 0.1464(4) 0.0225(7) 0.0955(19) Uani 1 1 d . . . . .
H21 H 0.667245 0.060761 0.016484 0.115 Uiso 1 1 calc R . . . .
C5 C 0.3016(7) 0.3350(6) 0.3162(5) 0.1019(18) Uani 1 1 d . . . . .
H5 H 0.290279 0.336532 0.391438 0.122 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
C8 S1 C17 105.79(16) . . ?
C10 N1 C12 112.1(3) . . ?
O1 C10 N1 123.7(3) . . ?
O1 C10 C9 129.6(3) . . ?
N1 C10 C9 106.7(3) . . ?
C2 C1 C7 120.3(3) . . ?
C6 C1 C7 122.0(3) . . ?
C6 C1 C2 117.7(4) . . ?
C11 C9 C10 105.4(3) . . ?
C8 C9 C10 124.8(3) . . ?
C8 C9 C11 129.7(3) . . ?
N1 C12 C11 109.1(3) . . ?
C13 C12 N1 128.4(3) . . ?
C13 C12 C11 122.5(3) . . ?
C8 C7 C1 114.0(3) . . ?
C12 C11 C9 106.7(3) . . ?
C16 C11 C9 135.3(3) . . ?
C16 C11 C12 118.0(3) . . ?
C12 C13 C14 118.0(3) . . ?
C18 C17 S1 120.7(3) . . ?
C22 C17 S1 120.2(3) . . ?
C22 C17 C18 118.9(4) . . ?
C15 C16 C11 119.6(3) . . ?
C9 C8 S1 118.2(3) . . ?
C9 C8 C7 122.9(3) . . ?
C7 C8 S1 118.9(2) . . ?
C3 C2 C1 121.5(4) . . ?
C15 C14 C13 120.8(3) . . ?
C14 C15 C16 121.1(3) . . ?
C19 C18 C17 120.4(5) . . ?
C4 C3 C2 119.6(4) . . ?
C17 C22 C21 120.1(5) . . ?
C1 C6 C5 120.7(4) . . ?
C3 C4 C5 119.9(4) . . ?
C20 C19 C18 120.4(6) . . ?
C19 C20 C21 120.3(5) . . ?
C20 C21 C22 119.9(5) . . ?
C4 C5 C6 120.6(5) . . ?
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 C17 1.758(3) . ?
S1 C8 1.738(3) . ?
O1 C10 1.229(4) . ?
N1 C10 1.357(4) . ?
N1 C12 1.388(4) . ?
C10 C9 1.487(4) . ?
C1 C7 1.510(5) . ?
C1 C2 1.376(4) . ?
C1 C6 1.362(5) . ?
C9 C11 1.477(4) . ?
C9 C8 1.354(4) . ?
C12 C11 1.404(4) . ?
C12 C13 1.372(4) . ?
C7 C8 1.510(4) . ?
C11 C16 1.385(4) . ?
C13 C14 1.377(5) . ?
C17 C18 1.371(5) . ?
C17 C22 1.363(5) . ?
C16 C15 1.380(5) . ?
C2 C3 1.375(5) . ?
C14 C15 1.374(5) . ?
C18 C19 1.360(6) . ?
C3 C4 1.348(6) . ?
C22 C21 1.377(6) . ?
C6 C5 1.371(6) . ?
C4 C5 1.358(6) . ?
C19 C20 1.347(8) . ?
C20 C21 1.352(8) . ?
