# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd1683c
_database_code_depnum_ccdc_archive 'CCDC 2091570'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_audit_creation_date             2018-04-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H18 O3 S'
_chemical_formula_sum            'C13 H18 O3 S'
_chemical_formula_weight         254.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         S1o4C20H20
_chemical_oxdiff_usercomment     'bicyclooctane with C=O'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   6.8529(2)
_cell_length_b                   9.2662(3)
_cell_length_c                   19.1898(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.051(2)
_cell_angle_gamma                90
_cell_volume                     1218.56(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4836
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      30.2930
_cell_measurement_theta_min      3.0420
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13700
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.441
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  80.00   1.00   35.00    --   -9.70  69.00 -26.00  122
  2  ω    -34.00  80.00   1.00   35.00    --   -9.70  38.00  90.00  114
  3  ω    -99.00 -74.00   1.00   35.00    --   -9.70 -72.00 120.00   25
  4  ω    -34.00  80.00   1.00   35.00    --   -9.70  38.00-150.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0139358000
_diffrn_orient_matrix_UB_12      -0.0029448000
_diffrn_orient_matrix_UB_13      0.0365864000
_diffrn_orient_matrix_UB_21      -0.0645250000
_diffrn_orient_matrix_UB_22      -0.0597520000
_diffrn_orient_matrix_UB_23      0.0019933000
_diffrn_orient_matrix_UB_31      0.0797817000
_diffrn_orient_matrix_UB_32      -0.0477517000
_diffrn_orient_matrix_UB_33      -0.0047438000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2728
_reflns_number_total             2778
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.051
_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+1.4500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C2(H2A,H2B), C7(H7A,H7B), C10(H10A,H10B), C4(H4A,
 H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12)
2.d X=CH2 refined with riding coordinates:
 C13(H13A,H13B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.74710(5) 0.28508(4) 0.77991(2) 0.01020(11) Uani 1 1 d . . . . .
O1 O 0.69012(17) 0.43412(12) 0.78819(6) 0.0154(2) Uani 1 1 d . . . . .
O3 O 0.46996(16) 0.32965(12) 0.66170(6) 0.0143(2) Uani 1 1 d . . . . .
O2 O 0.91516(17) 0.23558(13) 0.81903(6) 0.0174(3) Uani 1 1 d . . . . .
C6 C 0.6293(2) 0.29143(16) 0.64122(8) 0.0105(3) Uani 1 1 d . . . . .
C1 C 0.7999(2) 0.25150(16) 0.68879(7) 0.0094(3) Uani 1 1 d . . . . .
C11 C 0.5474(2) 0.17008(18) 0.80215(8) 0.0149(3) Uani 1 1 d . . . . .
H11A H 0.429928 0.198640 0.775456 0.018 Uiso 1 1 calc R . . . .
H11B H 0.579451 0.068877 0.790209 0.018 Uiso 1 1 calc R . . . .
C8 C 1.0309(2) 0.32178(17) 0.59266(8) 0.0135(3) Uani 1 1 d . . . . .
H8 H 1.146684 0.382271 0.580315 0.016 Uiso 1 1 calc R . . . .
C9 C 1.0806(2) 0.16207(18) 0.58112(8) 0.0150(3) Uani 1 1 d . . . . .
H9A H 1.117849 0.146213 0.531872 0.018 Uiso 1 1 calc R . . . .
H9B H 1.192530 0.134405 0.610918 0.018 Uiso 1 1 calc R . . . .
C2 C 0.8498(2) 0.09042(16) 0.67630(8) 0.0125(3) Uani 1 1 d . . . . .
H2A H 0.960901 0.061571 0.706244 0.015 Uiso 1 1 calc R . . . .
H2B H 0.736241 0.029374 0.688401 0.015 Uiso 1 1 calc R . . . .
C12 C 0.5082(2) 0.18253(18) 0.87864(8) 0.0149(3) Uani 1 1 d . . . . .
H12 H 0.610965 0.161136 0.910248 0.018 Uiso 1 1 calc R . . . .
C3 C 0.9033(2) 0.06905(17) 0.59919(8) 0.0140(3) Uani 1 1 d . . . . .
H3 H 0.936111 -0.034744 0.591080 0.017 Uiso 1 1 calc R . . . .
C7 C 0.9778(2) 0.34719(17) 0.66934(8) 0.0122(3) Uani 1 1 d . . . . .
H7A H 0.945288 0.450157 0.676743 0.015 Uiso 1 1 calc R . . . .
H7B H 1.090282 0.322562 0.699463 0.015 Uiso 1 1 calc R . . . .
C5 C 0.6791(2) 0.27151(18) 0.56501(8) 0.0147(3) Uani 1 1 d . . . . .
H5 H 0.565334 0.299830 0.535348 0.018 Uiso 1 1 calc R . . . .
C10 C 0.8585(2) 0.36421(18) 0.54618(8) 0.0155(3) Uani 1 1 d . . . . .
H10A H 0.893050 0.349151 0.496627 0.019 Uiso 1 1 calc R . . . .
H10B H 0.827559 0.467641 0.552880 0.019 Uiso 1 1 calc R . . . .
C13 C 0.3382(2) 0.22166(19) 0.90415(9) 0.0186(3) Uani 1 1 d . . . . .
H13A H 0.233214 0.243600 0.873592 0.022 Uiso 1 1 calc R . . . .
H13B H 0.320459 0.227987 0.953149 0.022 Uiso 1 1 calc R . . . .
C4 C 0.7281(2) 0.11045(18) 0.55351(8) 0.0163(3) Uani 1 1 d . . . . .
H4A H 0.614059 0.050140 0.565892 0.020 Uiso 1 1 calc R . . . .
H4B H 0.759571 0.093385 0.503851 0.020 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.01095(19) 0.01030(19) 0.00936(17) -0.00106(13) -0.00179(13) -0.00114(14)
O1 0.0189(6) 0.0117(6) 0.0156(5) -0.0033(4) -0.0004(4) -0.0002(4)
O3 0.0102(5) 0.0157(6) 0.0170(6) -0.0001(4) -0.0012(4) 0.0012(4)
O2 0.0164(6) 0.0221(6) 0.0138(5) -0.0003(5) -0.0049(4) 0.0029(5)
C6 0.0126(7) 0.0070(7) 0.0120(7) 0.0002(5) -0.0021(5) -0.0018(6)
C1 0.0092(7) 0.0105(7) 0.0086(6) -0.0002(5) -0.0008(5) 0.0004(5)
C11 0.0171(8) 0.0149(8) 0.0127(7) 0.0002(6) 0.0015(6) -0.0051(6)
C8 0.0122(7) 0.0138(8) 0.0145(7) 0.0010(6) 0.0025(6) -0.0011(6)
C9 0.0138(8) 0.0161(8) 0.0150(7) 0.0002(6) 0.0028(6) 0.0023(6)
C2 0.0149(8) 0.0096(7) 0.0131(7) 0.0001(6) 0.0024(6) 0.0016(6)
C12 0.0158(8) 0.0179(8) 0.0110(7) 0.0021(6) -0.0017(6) -0.0005(6)
C3 0.0175(8) 0.0096(7) 0.0149(7) -0.0021(6) 0.0027(6) 0.0009(6)
C7 0.0111(7) 0.0122(7) 0.0133(7) -0.0008(6) -0.0007(6) -0.0018(6)
C5 0.0132(8) 0.0195(8) 0.0113(7) 0.0004(6) -0.0028(6) 0.0016(6)
C10 0.0178(8) 0.0165(8) 0.0122(7) 0.0034(6) 0.0017(6) 0.0022(6)
C13 0.0177(8) 0.0202(9) 0.0178(8) -0.0020(6) -0.0003(6) 0.0026(7)
C4 0.0181(8) 0.0191(8) 0.0119(7) -0.0050(6) 0.0003(6) -0.0031(6)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.4440(12) . ?
S1 O2 1.4487(12) . ?
S1 C1 1.8128(15) . ?
S1 C11 1.7862(16) . ?
O3 C6 1.2136(19) . ?
C6 C1 1.528(2) . ?
C6 C5 1.513(2) . ?
C1 C2 1.550(2) . ?
C1 C7 1.553(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.497(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.535(2) . ?
C8 C7 1.534(2) . ?
C8 C10 1.531(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C3 1.530(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.537(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.315(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.534(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C5 H5 1.0000 . ?
C5 C10 1.543(2) . ?
C5 C4 1.546(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
O1 S1 O2 117.43(7) . . ?
O1 S1 C1 108.93(7) . . ?
O1 S1 C11 109.70(8) . . ?
O2 S1 C1 106.64(7) . . ?
O2 S1 C11 107.23(8) . . ?
C11 S1 C1 106.35(7) . . ?
O3 C6 C1 124.43(13) . . ?
O3 C6 C5 123.52(14) . . ?
C5 C6 C1 112.00(12) . . ?
C6 C1 S1 112.43(10) . . ?
C6 C1 C2 108.05(12) . . ?
C6 C1 C7 108.56(12) . . ?
C2 C1 S1 111.02(10) . . ?
C2 C1 C7 109.82(12) . . ?
C7 C1 S1 106.93(10) . . ?
S1 C11 H11A 109.9 . . ?
S1 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 S1 109.06(11) . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C9 C8 H8 109.3 . . ?
C7 C8 H8 109.3 . . ?
C7 C8 C9 109.83(13) . . ?
C10 C8 H8 109.3 . . ?
C10 C8 C9 109.56(13) . . ?
C10 C8 C7 109.60(13) . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C3 C9 C8 109.51(13) . . ?
C3 C9 H9A 109.8 . . ?
C3 C9 H9B 109.8 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 C1 109.00(12) . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C11 C12 H12 118.4 . . ?
C13 C12 C11 123.12(15) . . ?
C13 C12 H12 118.4 . . ?
C9 C3 C2 109.61(13) . . ?
C9 C3 H3 109.1 . . ?
C9 C3 C4 110.53(13) . . ?
C2 C3 H3 109.1 . . ?
C4 C3 C2 109.32(13) . . ?
C4 C3 H3 109.1 . . ?
C1 C7 H7A 109.8 . . ?
C1 C7 H7B 109.8 . . ?
C8 C7 C1 109.27(12) . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C6 C5 H5 110.0 . . ?
C6 C5 C10 109.81(13) . . ?
C6 C5 C4 107.75(13) . . ?
C10 C5 H5 110.0 . . ?
C10 C5 C4 109.33(13) . . ?
C4 C5 H5 110.0 . . ?
C8 C10 C5 109.59(13) . . ?
C8 C10 H10A 109.8 . . ?
C8 C10 H10B 109.8 . . ?
C5 C10 H10A 109.8 . . ?
C5 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
C3 C4 C5 109.26(13) . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
C5 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.072
_oxdiff_exptl_absorpt_empirical_full_min 0.928
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd1695c
_database_code_depnum_ccdc_archive 'CCDC 2091573'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_audit_creation_date             2018-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H21 N O3 S'
_chemical_formula_sum            'C14 H21 N O3 S'
_chemical_formula_weight         283.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H20NSO2
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.1940(2)
_cell_length_b                   10.5230(3)
_cell_length_c                   15.2153(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1472.06(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7797
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      28.6990
_cell_measurement_theta_min      2.5680
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14833
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.353
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  31.00   1.00   50.00    --   -7.50 -18.00   5.00  127
  2  ω    -20.00  71.00   1.00   50.00    --    4.20  38.00  60.00   91
  3  ω    -89.00  16.00   1.00   50.00    --   -7.50 -38.00-180.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0726704000
_diffrn_orient_matrix_UB_12      0.0226063000
_diffrn_orient_matrix_UB_13      -0.0000876000
_diffrn_orient_matrix_UB_21      0.0251033000
_diffrn_orient_matrix_UB_22      -0.0614651000
_diffrn_orient_matrix_UB_23      0.0116774000
_diffrn_orient_matrix_UB_31      0.0063495000
_diffrn_orient_matrix_UB_32      -0.0159001000
_diffrn_orient_matrix_UB_33      -0.0451411000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                3267
_reflns_number_total             3329
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1288 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.059
_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)+(0.0400P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0786
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C6(H6), C1(H1A)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C2(H2A,H2B)
2.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C12(H12), C9(H9)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.41468(5) 0.71705(5) 0.42625(3) 0.01297(13) Uani 1 1 d . . . . .
O2 O 0.51436(18) 0.80521(16) 0.38595(10) 0.0197(4) Uani 1 1 d . . . . .
O1 O 0.26144(15) 0.74770(16) 0.42545(11) 0.0217(4) Uani 1 1 d . . . . .
O3 O 0.60775(17) 0.11855(15) 0.59236(10) 0.0197(4) Uani 1 1 d . . . . .
N1 N 0.46402(19) 0.70502(17) 0.52742(11) 0.0134(4) Uani 1 1 d . . . . .
H1 H 0.555890 0.689991 0.529691 0.016 Uiso 1 1 d R . . . .
C7 C 0.4430(2) 0.4881(2) 0.59214(12) 0.0133(4) Uani 1 1 d . . . . .
C6 C 0.3883(2) 0.6237(2) 0.59252(13) 0.0146(4) Uani 1 1 d . . . . .
H6 H 0.282284 0.622793 0.577842 0.018 Uiso 1 1 calc R . . . .
C8 C 0.3489(2) 0.3863(2) 0.58057(14) 0.0154(4) Uani 1 1 d . . . . .
H8 H 0.248072 0.402591 0.572684 0.018 Uiso 1 1 calc R . . . .
C11 C 0.6421(3) 0.3377(2) 0.60289(14) 0.0167(5) Uani 1 1 d . . . . .
H11 H 0.743050 0.321462 0.610310 0.020 Uiso 1 1 calc R . . . .
C12 C 0.5911(3) 0.4612(2) 0.60359(13) 0.0149(4) Uani 1 1 d . . . . .
H12 H 0.657702 0.529159 0.611983 0.018 Uiso 1 1 calc R . . . .
C9 C 0.3979(2) 0.2609(2) 0.58016(14) 0.0172(4) Uani 1 1 d . . . . .
H9 H 0.331238 0.192819 0.572367 0.021 Uiso 1 1 calc R . . . .
C10 C 0.5456(2) 0.2367(2) 0.59130(13) 0.0156(4) Uani 1 1 d . . . . .
C1 C 0.4314(2) 0.5664(2) 0.37408(14) 0.0152(4) Uani 1 1 d . . . . .
H1A H 0.367053 0.503504 0.404324 0.018 Uiso 1 1 calc R . . . .
C3 C 0.6290(3) 0.4931(3) 0.27813(15) 0.0267(6) Uani 1 1 d . . . . .
H3A H 0.733009 0.511402 0.266923 0.032 Uiso 1 1 calc R . . . .
H3B H 0.608558 0.403867 0.261701 0.032 Uiso 1 1 calc R . . . .
C13 C 0.4072(3) 0.6870(2) 0.68238(14) 0.0214(5) Uani 1 1 d . . . . .
H13A H 0.511008 0.697692 0.694847 0.032 Uiso 1 1 calc GR . . . .
H13B H 0.362998 0.633421 0.727830 0.032 Uiso 1 1 calc GR . . . .
H13C H 0.359534 0.770278 0.682010 0.032 Uiso 1 1 calc GR . . . .
C4 C 0.5318(3) 0.5842(3) 0.22712(15) 0.0243(6) Uani 1 1 d . . . . .
H4A H 0.520905 0.556719 0.165236 0.029 Uiso 1 1 calc R . . . .
H4B H 0.571261 0.671702 0.228367 0.029 Uiso 1 1 calc R . . . .
C5 C 0.3875(3) 0.5762(3) 0.27605(15) 0.0223(5) Uani 1 1 d . . . . .
H5A H 0.331642 0.500463 0.257459 0.027 Uiso 1 1 calc R . . . .
H5B H 0.328007 0.653109 0.265382 0.027 Uiso 1 1 calc R . . . .
C2 C 0.5901(3) 0.5176(2) 0.37526(14) 0.0211(5) Uani 1 1 d . . . . .
H2A H 0.655860 0.582113 0.401090 0.025 Uiso 1 1 calc R . . . .
H2B H 0.597812 0.438346 0.409960 0.025 Uiso 1 1 calc R . . . .
C14 C 0.5130(3) 0.0119(2) 0.5840(2) 0.0330(7) Uani 1 1 d . . . . .
H14A H 0.463579 0.015230 0.527010 0.049 Uiso 1 1 calc GR . . . .
H14B H 0.440559 0.013826 0.631261 0.049 Uiso 1 1 calc GR . . . .
H14C H 0.569766 -0.066734 0.588101 0.049 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0115(2) 0.0116(2) 0.0159(2) 0.0030(2) -0.00036(19) 0.0006(2)
O2 0.0222(8) 0.0177(9) 0.0192(8) 0.0052(7) 0.0014(6) -0.0055(7)
O1 0.0147(7) 0.0242(9) 0.0263(8) 0.0038(7) -0.0006(6) 0.0065(6)
O3 0.0192(9) 0.0113(7) 0.0285(9) -0.0007(6) 0.0039(7) -0.0003(7)
N1 0.0116(8) 0.0128(9) 0.0157(8) 0.0014(7) -0.0002(6) -0.0001(7)
C7 0.0162(11) 0.0156(10) 0.0079(9) 0.0013(8) 0.0002(7) -0.0015(8)
C6 0.0136(10) 0.0143(10) 0.0159(10) 0.0010(8) 0.0019(8) -0.0026(8)
C8 0.0110(9) 0.0174(11) 0.0177(10) 0.0011(9) -0.0005(9) -0.0015(8)
C11 0.0132(10) 0.0190(12) 0.0181(10) 0.0030(9) -0.0009(8) -0.0011(9)
C12 0.0150(10) 0.0138(10) 0.0160(9) 0.0023(8) -0.0034(9) -0.0060(9)
C9 0.0154(10) 0.0153(10) 0.0208(10) -0.0010(8) -0.0005(9) -0.0068(9)
C10 0.0203(10) 0.0139(11) 0.0127(10) 0.0003(8) 0.0028(8) 0.0002(9)
C1 0.0146(10) 0.0135(10) 0.0174(10) -0.0013(8) 0.0001(8) -0.0003(9)
C3 0.0269(13) 0.0332(15) 0.0199(11) -0.0094(11) 0.0031(10) 0.0054(11)
C13 0.0286(12) 0.0187(11) 0.0169(10) -0.0026(9) 0.0062(10) -0.0021(11)
C4 0.0257(12) 0.0316(15) 0.0155(11) -0.0048(10) 0.0012(9) -0.0030(11)
C5 0.0212(12) 0.0287(14) 0.0170(11) -0.0012(9) -0.0041(9) -0.0040(11)
C2 0.0214(11) 0.0242(12) 0.0175(10) -0.0031(9) -0.0008(10) 0.0084(11)
C14 0.0287(14) 0.0125(12) 0.0577(19) -0.0060(12) 0.0039(13) -0.0024(10)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O2 1.4409(16) . ?
S1 O1 1.4454(15) . ?
S1 N1 1.6098(17) . ?
S1 C1 1.780(2) . ?
O3 C10 1.368(3) . ?
O3 C14 1.427(3) . ?
N1 H1 0.8600 . ?
N1 C6 1.483(3) . ?
C7 C6 1.513(3) . ?
C7 C8 1.388(3) . ?
C7 C12 1.402(3) . ?
C6 H6 1.0000 . ?
C6 C13 1.531(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.395(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C11 C10 1.396(3) . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C1 H1A 1.0000 . ?
C1 C5 1.549(3) . ?
C1 C2 1.547(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.523(4) . ?
C3 C2 1.542(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.523(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
O2 S1 O1 118.21(10) . . ?
O2 S1 N1 106.16(9) . . ?
O2 S1 C1 109.19(10) . . ?
O1 S1 N1 107.47(9) . . ?
O1 S1 C1 106.22(10) . . ?
N1 S1 C1 109.40(10) . . ?
C10 O3 C14 117.31(18) . . ?
S1 N1 H1 109.2 . . ?
C6 N1 S1 123.50(14) . . ?
C6 N1 H1 109.2 . . ?
C8 C7 C6 121.40(19) . . ?
C8 C7 C12 117.8(2) . . ?
C12 C7 C6 120.84(18) . . ?
N1 C6 C7 112.70(17) . . ?
N1 C6 H6 108.3 . . ?
N1 C6 C13 107.01(17) . . ?
C7 C6 H6 108.3 . . ?
C7 C6 C13 112.09(17) . . ?
C13 C6 H6 108.3 . . ?
C7 C8 H8 119.0 . . ?
C7 C8 C9 121.96(19) . . ?
C9 C8 H8 119.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.1(2) . . ?
C10 C11 H11 120.0 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.2(2) . . ?
C11 C12 H12 119.4 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.20(19) . . ?
C10 C9 H9 120.4 . . ?
O3 C10 C11 115.12(19) . . ?
O3 C10 C9 125.1(2) . . ?
C9 C10 C11 119.8(2) . . ?
S1 C1 H1A 109.5 . . ?
C5 C1 S1 110.34(16) . . ?
C5 C1 H1A 109.5 . . ?
C2 C1 S1 111.83(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 C5 106.20(17) . . ?
H3A C3 H3B 108.9 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C4 C3 C2 104.30(19) . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
C3 C4 C5 103.1(2) . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C1 C5 H5A 110.9 . . ?
C1 C5 H5B 110.9 . . ?
C4 C5 C1 104.33(18) . . ?
C4 C5 H5A 110.9 . . ?
C4 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C3 C2 C1 105.26(18) . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.097
_oxdiff_exptl_absorpt_empirical_full_min 0.869
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd1667
_database_code_depnum_ccdc_archive 'CCDC 2092038'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2021-06-24 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_audit_creation_date             2018-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H19 N O3 S'
_chemical_formula_sum            'C10 H19 N O3 S'
_chemical_formula_weight         233.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H12S1O3N1
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   11.7797(3)
_cell_length_b                   10.1425(2)
_cell_length_c                   9.6720(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.019(2)
_cell_angle_gamma                90
_cell_volume                     1149.20(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8601
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      30.2940
_cell_measurement_theta_min      2.5850
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.656
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00  30.00   1.00   20.00    --    4.20 -44.00  70.00  115
  2  ω    -35.00  80.00   1.00   20.00    --   -9.90  44.00-139.00  115
  3  ω    -34.00  80.00   1.00   20.00    --   -9.90  38.00  60.00  114
  4  ω    -34.00  80.00   1.00   20.00    --   -9.90  38.00 -30.00  114
  5  ω    -99.00 -40.00   1.00   20.00    --   -9.90 -72.00 120.00   59
  6  ω    -99.00  22.00   1.00   20.00    --   -9.90 -72.00 -60.00  121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0063620000
_diffrn_orient_matrix_UB_12      -0.0317138000
_diffrn_orient_matrix_UB_13      -0.0657241000
_diffrn_orient_matrix_UB_21      0.0550001000
_diffrn_orient_matrix_UB_22      0.0222633000
_diffrn_orient_matrix_UB_23      -0.0128507000
_diffrn_orient_matrix_UB_31      0.0244766000
_diffrn_orient_matrix_UB_32      -0.0582258000
_diffrn_orient_matrix_UB_33      0.0308853000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2630
_reflns_number_total             2642
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.036
_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)+(0.0390P)²+0.9500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0848
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C6(H6A,H6B), C2(H2A,H2B), C3(H3A,H3B), C9(H9A,H9B), C1(H1A,
 H1B), C8(H8A,H8B), C7(H7A,H7B), C4(H4A,H4B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.74661(3) 0.42001(3) 0.48070(3) 0.00944(10) Uani 1 1 d . . . . .
O2 O 0.84855(8) 0.35098(10) 0.53482(10) 0.0145(2) Uani 1 1 d . . . . .
O3 O 0.68948(8) 0.50341(10) 0.57221(10) 0.0153(2) Uani 1 1 d . . . . .
O1 O 0.49202(8) 0.11445(10) 0.33314(11) 0.0191(2) Uani 1 1 d . . . . .
N1 N 0.65489(9) 0.30688(11) 0.42369(12) 0.0109(2) Uani 1 1 d . . . . .
C5 C 0.77879(10) 0.52174(12) 0.33834(13) 0.0096(2) Uani 1 1 d . . . . .
H5 H 0.705811 0.559272 0.292602 0.011 Uiso 1 1 calc R . . . .
C10 C 0.83566(12) 0.44178(13) 0.23048(14) 0.0140(3) Uani 1 1 d . . . . .
H10A H 0.781200 0.375362 0.187810 0.017 Uiso 1 1 calc R . . . .
H10B H 0.902712 0.394498 0.276764 0.017 Uiso 1 1 calc R . . . .
C6 C 0.85432(11) 0.63574(13) 0.39831(14) 0.0136(3) Uani 1 1 d . . . . .
H6A H 0.810904 0.690219 0.459465 0.016 Uiso 1 1 calc R . . . .
H6B H 0.921795 0.599512 0.455450 0.016 Uiso 1 1 calc R . . . .
C2 C 0.69116(11) 0.18323(13) 0.36215(14) 0.0133(3) Uani 1 1 d . . . . .
H2A H 0.768122 0.157877 0.404838 0.016 Uiso 1 1 calc R . . . .
H2B H 0.694081 0.194362 0.260894 0.016 Uiso 1 1 calc R . . . .
C3 C 0.53978(11) 0.34652(14) 0.36537(15) 0.0148(3) Uani 1 1 d . . . . .
H3A H 0.538180 0.362322 0.264176 0.018 Uiso 1 1 calc R . . . .
H3B H 0.516968 0.428825 0.410036 0.018 Uiso 1 1 calc R . . . .
C9 C 0.87370(12) 0.53209(14) 0.11712(14) 0.0150(3) Uani 1 1 d . . . . .
H9A H 0.913392 0.479116 0.050917 0.018 Uiso 1 1 calc R . . . .
H9B H 0.805752 0.572817 0.065075 0.018 Uiso 1 1 calc R . . . .
C1 C 0.60504(12) 0.07776(13) 0.38924(15) 0.0159(3) Uani 1 1 d . . . . .
H1A H 0.626340 -0.006211 0.346611 0.019 Uiso 1 1 calc R . . . .
H1B H 0.606477 0.063577 0.490680 0.019 Uiso 1 1 calc R . . . .
C8 C 0.95365(11) 0.64051(14) 0.17942(14) 0.0150(3) Uani 1 1 d . . . . .
H8A H 1.023699 0.600312 0.227117 0.018 Uiso 1 1 calc R . . . .
H8B H 0.976080 0.698171 0.104302 0.018 Uiso 1 1 calc R . . . .
C7 C 0.89405(12) 0.72247(14) 0.28304(14) 0.0158(3) Uani 1 1 d . . . . .
H7A H 0.827367 0.767949 0.233544 0.019 Uiso 1 1 calc R . . . .
H7B H 0.947297 0.790527 0.324834 0.019 Uiso 1 1 calc R . . . .
C4 C 0.45874(12) 0.23557(14) 0.39266(17) 0.0198(3) Uani 1 1 d . . . . .
H4A H 0.457818 0.224206 0.494197 0.024 Uiso 1 1 calc R . . . .
H4B H 0.380516 0.258910 0.352657 0.024 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.00926(16) 0.01035(16) 0.00885(16) -0.00015(11) 0.00153(11) -0.00170(11)
O2 0.0120(5) 0.0162(5) 0.0145(5) 0.0034(4) -0.0021(4) -0.0007(4)
O3 0.0170(5) 0.0161(5) 0.0137(5) -0.0038(4) 0.0063(4) -0.0027(4)
O1 0.0135(5) 0.0140(5) 0.0291(6) -0.0054(4) -0.0014(4) -0.0026(4)
N1 0.0084(5) 0.0093(5) 0.0150(5) -0.0013(4) 0.0011(4) -0.0007(4)
C5 0.0100(6) 0.0093(6) 0.0095(6) 0.0018(4) 0.0016(4) -0.0006(4)
C10 0.0182(7) 0.0117(6) 0.0130(6) -0.0008(5) 0.0059(5) -0.0011(5)
C6 0.0145(6) 0.0131(6) 0.0135(6) -0.0022(5) 0.0032(5) -0.0049(5)
C2 0.0131(6) 0.0100(6) 0.0171(6) -0.0015(5) 0.0039(5) -0.0004(5)
C3 0.0103(6) 0.0127(6) 0.0208(7) -0.0015(5) -0.0017(5) 0.0009(5)
C9 0.0171(6) 0.0172(7) 0.0112(6) -0.0008(5) 0.0037(5) -0.0035(5)
C1 0.0145(6) 0.0110(6) 0.0222(7) 0.0000(5) 0.0013(5) -0.0015(5)
C8 0.0131(6) 0.0183(7) 0.0137(6) 0.0026(5) 0.0019(5) -0.0036(5)
C7 0.0170(6) 0.0137(6) 0.0170(7) 0.0005(5) 0.0028(5) -0.0048(5)
C4 0.0117(6) 0.0161(7) 0.0316(8) -0.0052(6) 0.0016(6) -0.0020(5)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O2 1.4403(10) . ?
S1 O3 1.4410(10) . ?
S1 N1 1.6318(11) . ?
S1 C5 1.7927(12) . ?
O1 C1 1.4331(17) . ?
O1 C4 1.4288(17) . ?
N1 C2 1.4707(16) . ?
N1 C3 1.4690(16) . ?
C5 H5 1.0000 . ?
C5 C10 1.5301(17) . ?
C5 C6 1.5352(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.5314(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5314(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.5158(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5166(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.5297(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.5283(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
O2 S1 O3 119.17(6) . . ?
O2 S1 N1 106.16(6) . . ?
O2 S1 C5 108.87(6) . . ?
O3 S1 N1 106.56(6) . . ?
O3 S1 C5 106.49(6) . . ?
N1 S1 C5 109.33(6) . . ?
C4 O1 C1 110.73(10) . . ?
C2 N1 S1 121.75(8) . . ?
C3 N1 S1 119.28(9) . . ?
C3 N1 C2 111.93(10) . . ?
S1 C5 H5 108.5 . . ?
C10 C5 S1 111.20(9) . . ?
C10 C5 H5 108.5 . . ?
C10 C5 C6 112.27(10) . . ?
C6 C5 S1 107.71(9) . . ?
C6 C5 H5 108.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 C9 110.67(11) . . ?
H10A C10 H10B 108.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.52(11) . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
N1 C2 H2A 110.2 . . ?
N1 C2 H2B 110.2 . . ?
N1 C2 C1 107.68(10) . . ?
H2A C2 H2B 108.5 . . ?
C1 C2 H2A 110.2 . . ?
C1 C2 H2B 110.2 . . ?
N1 C3 H3A 110.2 . . ?
N1 C3 H3B 110.2 . . ?
N1 C3 C4 107.61(11) . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C8 C9 C10 111.23(11) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
O1 C1 C2 111.30(11) . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C7 C8 C9 110.07(11) . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 C6 111.19(11) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O1 C4 C3 111.32(11) . . ?
O1 C4 H4A 109.4 . . ?
O1 C4 H4B 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.120
_oxdiff_exptl_absorpt_empirical_full_min 0.865
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd1690
_database_code_depnum_ccdc_archive 'CCDC 2091572'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_audit_creation_date             2018-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 Cl N O2 S'
_chemical_formula_sum            'C15 H16 Cl N O2 S'
_chemical_formula_weight         309.80
_chemical_melting_point          ?
_chemical_oxdiff_formula         S1Cl1O2N1C20h18
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5955(2)
_cell_length_b                   10.7380(3)
_cell_length_c                   11.8452(3)
_cell_angle_alpha                99.357(2)
_cell_angle_beta                 93.406(2)
_cell_angle_gamma                90.654(3)
_cell_volume                     700.84(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8509
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      30.1250
_cell_measurement_theta_min      2.7880
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.840
_exptl_absorpt_coefficient_mu    0.422
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19342
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.376
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00  20.00   1.00   35.00    --   -9.70 -57.00 -30.00  119
  2  ω    -34.00  80.00   1.00   35.00    --   -9.70  38.00 120.00  114
  3  ω    -34.00  80.00   1.00   35.00    --   -9.70  38.00 -90.00  114
  4  ω    -99.00  20.00   1.00   35.00    --   -9.70 -57.00-180.00  119
  5  ω    -39.00  80.00   1.00   35.00    --   -9.70  57.00-180.00  119
  6  ω    -39.00  80.00   1.00   35.00    --   -9.70  57.00 -60.00  119
  7  ω    -39.00  45.00   1.00   35.00    --   -9.70  57.00  60.00   84
  8  ω    -34.00  80.00   1.00   35.00    --   -9.70  38.00   0.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0163832000
_diffrn_orient_matrix_UB_12      0.0392773000
_diffrn_orient_matrix_UB_13      0.0542418000
_diffrn_orient_matrix_UB_21      -0.0869033000
_diffrn_orient_matrix_UB_22      -0.0366378000
_diffrn_orient_matrix_UB_23      0.0219924000
_diffrn_orient_matrix_UB_31      0.0911724000
_diffrn_orient_matrix_UB_32      -0.0399848000
_diffrn_orient_matrix_UB_33      0.0164760000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3195
_reflns_number_total             3213
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      0.998
_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)+(0.0320P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0904
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B), C14(H14A,H14B), C13(H13A,H13B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.04229(7) 0.19393(4) 0.35837(3) 0.01630(11) Uani 1 1 d . . . . .
Cl1 Cl 0.89767(8) 0.16365(5) -0.07162(4) 0.02357(12) Uani 1 1 d . . . . .
O1 O 0.0360(2) 0.06261(13) 0.30686(11) 0.0220(3) Uani 1 1 d . . . . .
O2 O -0.1743(2) 0.24853(14) 0.40405(11) 0.0234(3) Uani 1 1 d . . . . .
N1 N 0.2440(3) 0.44376(14) 0.09685(13) 0.0194(3) Uani 1 1 d . . . . .
C6 C 0.3189(3) 0.25109(16) 0.18023(14) 0.0139(3) Uani 1 1 d . . . . .
C3 C 0.6763(3) 0.19983(17) 0.02508(14) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.5534(3) 0.30913(17) 0.02652(14) 0.0166(3) Uani 1 1 d . . . . .
H2 H 0.590885 0.366461 -0.023376 0.020 Uiso 1 1 calc R . . . .
C5 C 0.4551(3) 0.13971(16) 0.17633(14) 0.0159(3) Uani 1 1 d . . . . .
H5 H 0.424795 0.082325 0.227229 0.019 Uiso 1 1 calc R . . . .
C1 C 0.3695(3) 0.33593(16) 0.10323(14) 0.0150(3) Uani 1 1 d . . . . .
C7 C 0.1300(3) 0.28631(16) 0.25421(14) 0.0151(3) Uani 1 1 d . . . . .
C4 C 0.6296(3) 0.11422(17) 0.09989(15) 0.0170(3) Uani 1 1 d . . . . .
H4 H 0.718665 0.039142 0.097360 0.020 Uiso 1 1 calc R . . . .
C8 C 0.0043(3) 0.39332(17) 0.24592(15) 0.0189(4) Uani 1 1 d . . . . .
H8 H -0.123179 0.416570 0.294049 0.023 Uiso 1 1 calc R . . . .
C10 C 0.2766(3) 0.21997(16) 0.46981(14) 0.0155(3) Uani 1 1 d . . . . .
H10 H 0.432694 0.198550 0.435235 0.019 Uiso 1 1 calc R . . . .
C11 C 0.2316(3) 0.13065(17) 0.55528(15) 0.0196(4) Uani 1 1 d . . . . .
H11A H 0.072624 0.146958 0.586521 0.023 Uiso 1 1 calc R . . . .
H11B H 0.231721 0.042083 0.515600 0.023 Uiso 1 1 calc R . . . .
C9 C 0.0674(3) 0.46862(17) 0.16459(16) 0.0204(4) Uani 1 1 d . . . . .
H9 H -0.023466 0.541693 0.158543 0.024 Uiso 1 1 calc R . . . .
C15 C 0.2889(3) 0.35793(17) 0.52835(15) 0.0198(4) Uani 1 1 d . . . . .
H15A H 0.324448 0.412931 0.471731 0.024 Uiso 1 1 calc R . . . .
H15B H 0.132341 0.382127 0.559097 0.024 Uiso 1 1 calc R . . . .
C14 C 0.4840(3) 0.37632(18) 0.62593(15) 0.0204(4) Uani 1 1 d . . . . .
H14A H 0.642120 0.360218 0.593805 0.024 Uiso 1 1 calc R . . . .
H14B H 0.484690 0.464856 0.665730 0.024 Uiso 1 1 calc R . . . .
C13 C 0.4443(3) 0.28788(19) 0.71200(15) 0.0227(4) Uani 1 1 d . . . . .
H13A H 0.295292 0.310584 0.750820 0.027 Uiso 1 1 calc R . . . .
H13B H 0.579060 0.298316 0.771047 0.027 Uiso 1 1 calc R . . . .
C12 C 0.4258(4) 0.15039(18) 0.65329(16) 0.0230(4) Uani 1 1 d . . . . .
H12A H 0.388807 0.096151 0.710316 0.028 Uiso 1 1 calc R . . . .
H12B H 0.581922 0.124643 0.622801 0.028 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0123(2) 0.0238(2) 0.0130(2) 0.00421(16) 0.00065(14) -0.00489(15)
Cl1 0.0194(2) 0.0332(3) 0.0191(2) 0.00510(18) 0.00687(16) 0.00562(17)
O1 0.0249(7) 0.0244(7) 0.0166(6) 0.0044(5) -0.0004(5) -0.0092(5)
O2 0.0125(6) 0.0395(8) 0.0186(6) 0.0055(6) 0.0035(5) -0.0033(5)
N1 0.0201(7) 0.0185(7) 0.0204(7) 0.0059(6) -0.0009(6) 0.0018(6)
C6 0.0132(7) 0.0166(8) 0.0121(7) 0.0032(6) -0.0013(6) -0.0020(6)
C3 0.0131(8) 0.0224(9) 0.0126(7) 0.0004(6) 0.0012(6) -0.0003(6)
C2 0.0169(8) 0.0214(8) 0.0120(7) 0.0050(6) -0.0004(6) -0.0022(6)
C5 0.0175(8) 0.0171(8) 0.0137(8) 0.0048(6) -0.0008(6) 0.0000(6)
C1 0.0148(8) 0.0164(8) 0.0136(7) 0.0029(6) -0.0021(6) -0.0012(6)
C7 0.0125(7) 0.0209(8) 0.0119(7) 0.0039(6) -0.0012(6) -0.0034(6)
C4 0.0163(8) 0.0179(8) 0.0162(8) 0.0020(6) -0.0021(6) 0.0024(6)
C8 0.0140(8) 0.0240(9) 0.0177(8) 0.0009(7) 0.0007(6) 0.0015(7)
C10 0.0121(7) 0.0215(9) 0.0128(7) 0.0033(6) -0.0004(6) -0.0022(6)
C11 0.0202(9) 0.0208(9) 0.0187(8) 0.0063(7) 0.0007(7) -0.0028(7)
C9 0.0206(9) 0.0182(8) 0.0226(9) 0.0043(7) 0.0004(7) 0.0052(7)
C15 0.0209(9) 0.0211(9) 0.0176(8) 0.0055(7) -0.0033(7) -0.0029(7)
C14 0.0188(8) 0.0235(9) 0.0179(8) 0.0019(7) -0.0030(7) -0.0026(7)
C13 0.0237(9) 0.0290(10) 0.0149(8) 0.0034(7) -0.0018(7) 0.0008(7)
C12 0.0255(9) 0.0249(10) 0.0196(9) 0.0082(7) -0.0027(7) 0.0020(7)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.4417(14) . ?
S1 O2 1.4477(13) . ?
S1 C7 1.7905(17) . ?
S1 C10 1.7904(17) . ?
Cl1 C3 1.7414(17) . ?
N1 C1 1.371(2) . ?
N1 C9 1.312(2) . ?
C6 C5 1.421(2) . ?
C6 C1 1.427(2) . ?
C6 C7 1.428(2) . ?
C3 C2 1.365(2) . ?
C3 C4 1.409(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.414(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.371(2) . ?
C7 C8 1.368(2) . ?
C4 H4 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.412(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.533(2) . ?
C10 C15 1.529(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.530(2) . ?
C9 H9 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.529(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.526(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C12 1.526(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
O1 S1 O2 118.45(8) . . ?
O1 S1 C7 108.62(8) . . ?
O1 S1 C10 109.08(8) . . ?
O2 S1 C7 106.69(8) . . ?
O2 S1 C10 108.28(8) . . ?
C10 S1 C7 104.89(8) . . ?
C9 N1 C1 117.78(15) . . ?
C5 C6 C1 118.39(15) . . ?
C5 C6 C7 125.72(15) . . ?
C1 C6 C7 115.89(15) . . ?
C2 C3 Cl1 119.63(14) . . ?
C2 C3 C4 121.94(16) . . ?
C4 C3 Cl1 118.43(13) . . ?
C3 C2 H2 120.4 . . ?
C3 C2 C1 119.16(16) . . ?
C1 C2 H2 120.4 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.69(16) . . ?
C4 C5 H5 119.7 . . ?
N1 C1 C6 123.31(16) . . ?
N1 C1 C2 116.61(15) . . ?
C2 C1 C6 120.06(15) . . ?
C6 C7 S1 122.75(13) . . ?
C8 C7 S1 117.08(13) . . ?
C8 C7 C6 120.15(16) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.73(16) . . ?
C5 C4 H4 120.1 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.85(16) . . ?
C9 C8 H8 120.6 . . ?
S1 C10 H10 108.6 . . ?
C11 C10 S1 108.13(11) . . ?
C11 C10 H10 108.6 . . ?
C15 C10 S1 111.17(12) . . ?
C15 C10 H10 108.6 . . ?
C15 C10 C11 111.54(14) . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.19(14) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
N1 C9 C8 123.96(17) . . ?
N1 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
C10 C15 H15A 109.7 . . ?
C10 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C14 C15 C10 110.02(15) . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C13 C14 C15 111.54(15) . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C14 C13 C12 111.31(15) . . ?
H13A C13 H13B 108.0 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 C11 111.61(15) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.149
_oxdiff_exptl_absorpt_empirical_full_min 0.917
