# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_chq_0629
_database_code_depnum_ccdc_archive 'CCDC 1852757'
_audit_update_record             
;
2018-07-02 deposited with the CCDC.
2018-07-30 downloaded from the CCDC.
;
_audit_creation_date             2018-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        C22H22NO3S2
_chemical_formula_moiety         'C20 H15 N O2 S, C2 H6 O S'
_chemical_formula_sum            'C22 H21 N O3 S2'
_chemical_formula_weight         411.52
_chemical_absolute_configuration R
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H24NO3S2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   7.94450(9)
_cell_length_b                   10.19612(12)
_cell_length_c                   25.8377(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2092.94(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    26281
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1400
_cell_measurement_theta_min      4.6310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            43576
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.421
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_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     -8.00  18.00   1.00    6.17    --   34.00 101.00 -81.09   26
  2  ω      0.00  28.00   1.00    6.17    --   38.00  92.00  63.47   28
  3  ω    -69.00  32.00   1.00    6.17    --  -41.12  57.00-150.00  101
  4  ω   -113.00 -13.00   1.00    6.17    --  -41.12 -57.00-180.00  100
  5  ω   -116.00 -17.00   1.00    6.17    --  -41.12 -37.00-120.00   99
  6  ω    -96.00  -2.00   1.00    6.17    --  -41.12 125.00  30.00   94
  7  ω   -113.00 -13.00   1.00    6.17    --  -41.12 -57.00  60.00  100
  8  ω     23.00  97.00   1.00    6.17    --   41.12-125.00 -30.00   74
  9  ω      6.00  33.00   1.00    6.17    --   42.00  88.00 -35.32   27
 10  ω     21.00  47.00   1.00    6.17    --   54.00  79.00  37.81   26
 11  ω     21.00  47.00   1.00    6.17    --   54.00  79.00 -14.17   26
 12  ω     21.00  47.00   1.00    6.17    --   54.00  79.00 160.04   26
 13  ω     21.00  47.00   1.00    6.17    --   54.00  79.00 -80.54   26
 14  ω     20.00  46.00   1.00    6.17    --   54.00  81.00  98.15   26
 15  ω     26.00 133.00   1.00    6.17    --   58.00  75.00-127.59  107
 16  ω     33.00 142.00   1.00    6.17    --   66.00  77.00 154.00  109
 17  ω     33.00 142.00   1.00    6.17    --   66.00  77.00  65.39  109
 18  ω     34.00 141.00   1.00    6.17    --   66.00  75.00 -67.07  107
 19  ω     34.00 141.00   1.00    6.17    --   66.00  75.00-163.82  107
 20  ω     34.00 142.00   1.00    6.17    --   66.00  76.00-104.12  108
 21  ω     37.00 146.00   1.00    6.17    --   70.00  77.00  93.49  109
 22  ω     37.00 146.00   1.00    6.17    --   70.00  77.00  14.10  109
 23  ω     37.00 146.00   1.00    6.17    --   70.00  77.00 -31.31  109
 24  ω     49.00 158.00   1.00   24.67    --   82.00  77.00-150.36  109
 25  ω     58.00 157.00   1.00   24.67    --   90.00  76.00-139.91   99
 26  ω     75.00 168.00   1.00   24.67    --  107.82  77.00 -30.00   93
 27  ω     75.00 172.00   1.00   24.67    --  107.82  77.00 -60.00   97
 28  ω    134.00 160.00   1.00   24.67    --  107.82  61.00-120.00   26
 29  ω     80.00 111.00   1.00   24.67    --  107.82  61.00-120.00   31
 30  ω    119.00 173.00   1.00   24.67    --  107.82 125.00  90.00   54
 31  ω     35.00 120.00   1.00   24.67    --  107.82-125.00 -60.00   85
 32  ω     75.00 128.00   1.00   24.67    --  107.82  77.00  90.00   53
 33  ω     75.00 150.00   1.00   24.67    --  107.82  77.00-180.00   75
 34  ω     94.00 175.00   1.00   24.67    --  107.82 125.00-150.00   81
 35  ω     75.00 143.00   1.00   24.67    --  107.82  77.00 150.00   68
 36  ω     78.00 118.00   1.00   24.67    --  107.82  77.00-120.00   40
 37  ω     75.00 155.00   1.00   24.67    --  107.82  77.00 -90.00   80
 38  ω     75.00 176.00   1.00   24.67    --  107.82  77.00 120.00  101
 39  ω     32.00 121.00   1.00   24.67    --  107.82 -77.00 120.00   89
 40  ω     76.00 176.00   1.00   24.67    --  107.82  77.00   0.00  100
 41  ω     79.00 122.00   1.00   24.67    --  107.82  61.00  60.00   43
 42  ω     39.00 122.00   1.00   24.67    --  107.82-125.00  60.00   83
 43  ω     79.00 105.00   1.00   24.67    --  107.82  61.00  90.00   26
 44  ω     75.00 178.00   1.00   24.67    --  107.82  77.00  60.00  103
 45  ω     95.00 159.00   1.00   24.67    --  107.82 125.00-180.00   64
 46  ω    124.00 150.00   1.00   24.67    --  107.82  77.00  30.00   26
 47  ω     75.00 101.00   1.00   24.67    --  107.82  77.00  30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0821708000
_diffrn_orient_matrix_UB_12      0.0667086000
_diffrn_orient_matrix_UB_13      -0.0471505000
_diffrn_orient_matrix_UB_21      0.1523193000
_diffrn_orient_matrix_UB_22      -0.0386380000
_diffrn_orient_matrix_UB_23      -0.0336089000
_diffrn_orient_matrix_UB_31      -0.0874926000
_diffrn_orient_matrix_UB_32      -0.1299401000
_diffrn_orient_matrix_UB_33      -0.0142180000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3599
_reflns_number_total             3709
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.211
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1495 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3709
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.078
_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)+(0.0481P)²+0.5904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0905
_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 Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C18(H18), C5(H5), C8(H8), C6(H6), C19(H19), C20(H20), C7(H7),
 C10(H10), C11(H11), C14(H14), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.88173(11) 0.25822(7) 0.18613(3) 0.0536(2) Uani 1 1 d . . . . .
S2 S 0.30883(11) 0.19131(11) 0.29516(5) 0.0759(3) Uani 1 1 d . . . . .
O2 O 0.7852(3) 0.23872(19) 0.29645(7) 0.0471(5) Uani 1 1 d . . . . .
O1 O 1.0215(2) 0.5583(2) 0.42903(9) 0.0514(5) Uani 1 1 d . . . . .
N1 N 0.6554(3) 0.4284(2) 0.37188(10) 0.0464(6) Uani 1 1 d . . . . .
H1 H 0.594547 0.377055 0.353268 0.056 Uiso 1 1 calc R . . . .
C4 C 0.5967(3) 0.5366(3) 0.39614(9) 0.0363(5) Uani 1 1 d . . . . .
C3 C 0.7245(3) 0.6042(3) 0.42230(9) 0.0359(6) Uani 1 1 d . . . . .
O3 O 0.3667(4) 0.3157(3) 0.31879(13) 0.0880(9) Uani 1 1 d . . . . .
C2 C 0.8793(3) 0.5325(3) 0.41448(9) 0.0366(5) Uani 1 1 d . . . . .
C17 C 0.9458(3) 0.3559(3) 0.23638(10) 0.0382(6) Uani 1 1 d . . . . .
C1 C 0.8347(3) 0.4097(3) 0.38116(10) 0.0368(6) Uani 1 1 d . . . . .
C15 C 0.9327(3) 0.4241(3) 0.33045(10) 0.0381(6) Uani 1 1 d . . . . .
H15A H 0.918274 0.512851 0.317715 0.046 Uiso 1 1 calc R . . . .
H15B H 1.051501 0.411554 0.337577 0.046 Uiso 1 1 calc R . . . .
C16 C 0.8806(3) 0.3297(2) 0.28852(9) 0.0347(5) Uani 1 1 d . . . . .
C18 C 1.0565(4) 0.4558(3) 0.22025(10) 0.0479(7) Uani 1 1 d . . . . .
H18 H 1.106500 0.517661 0.241785 0.058 Uiso 1 1 calc R . . . .
C5 C 0.4305(3) 0.5837(3) 0.39744(11) 0.0448(6) Uani 1 1 d . . . . .
H5 H 0.343660 0.539439 0.380787 0.054 Uiso 1 1 calc R . . . .
C8 C 0.6912(4) 0.7206(3) 0.44892(10) 0.0433(6) Uani 1 1 d . . . . .
H8 H 0.777081 0.765770 0.465663 0.052 Uiso 1 1 calc R . . . .
C6 C 0.4013(4) 0.6983(3) 0.42443(12) 0.0514(7) Uani 1 1 d . . . . .
H6 H 0.292202 0.731236 0.425755 0.062 Uiso 1 1 calc R . . . .
C9 C 0.8761(4) 0.2866(3) 0.41179(10) 0.0434(6) Uani 1 1 d . . . . .
C19 C 1.0800(5) 0.4468(3) 0.16483(12) 0.0594(8) Uani 1 1 d . . . . .
H19 H 1.146265 0.504976 0.146034 0.071 Uiso 1 1 calc R . . . .
C20 C 0.9965(5) 0.3457(3) 0.14314(11) 0.0563(8) Uani 1 1 d . . . . .
H20 H 1.001443 0.326005 0.108027 0.068 Uiso 1 1 calc R . . . .
C7 C 0.5291(4) 0.7666(3) 0.44978(12) 0.0527(7) Uani 1 1 d . . . . .
H7 H 0.504214 0.843808 0.467363 0.063 Uiso 1 1 calc R . . . .
C10 C 0.7527(5) 0.2158(3) 0.43717(13) 0.0648(9) Uani 1 1 d . . . . .
H10 H 0.640247 0.239785 0.434062 0.078 Uiso 1 1 calc R . . . .
C11 C 0.7985(8) 0.1064(4) 0.46794(16) 0.0837(14) Uani 1 1 d . . . . .
H11 H 0.715847 0.059735 0.485574 0.100 Uiso 1 1 calc R . . . .
C14 C 1.0438(5) 0.2467(4) 0.41763(12) 0.0589(8) Uani 1 1 d . . . . .
H14 H 1.129042 0.293534 0.401280 0.071 Uiso 1 1 calc R . . . .
C12 C 0.9618(8) 0.0694(4) 0.47185(15) 0.0836(14) Uani 1 1 d . . . . .
H12 H 0.989946 -0.003971 0.491411 0.100 Uiso 1 1 calc R . . . .
C13 C 1.0841(6) 0.1380(4) 0.44760(15) 0.0783(12) Uani 1 1 d . . . . .
H13 H 1.195831 0.112313 0.450985 0.094 Uiso 1 1 calc R . . . .
C22 C 0.4075(7) 0.1786(7) 0.2342(2) 0.116(2) Uani 1 1 d . . . . .
H22A H 0.379702 0.254003 0.213674 0.174 Uiso 1 1 calc GR . . . .
H22B H 0.369248 0.100704 0.217035 0.174 Uiso 1 1 calc GR . . . .
H22C H 0.527278 0.174336 0.238851 0.174 Uiso 1 1 calc GR . . . .
C21 C 0.4208(8) 0.0656(6) 0.3285(3) 0.123(2) Uani 1 1 d . . . . .
H21A H 0.539573 0.081544 0.325783 0.185 Uiso 1 1 calc GR . . . .
H21B H 0.394651 -0.017956 0.313375 0.185 Uiso 1 1 calc GR . . . .
H21C H 0.388527 0.065467 0.364307 0.185 Uiso 1 1 calc GR . . . .


_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 C17 1.714(3) . ?
S1 C20 1.691(3) . ?
S2 O3 1.481(3) . ?
S2 C22 1.763(5) . ?
S2 C21 1.782(7) . ?
O2 C16 1.215(3) . ?
O1 C2 1.219(3) . ?
N1 H1 0.8600 . ?
N1 C4 1.351(4) . ?
N1 C1 1.457(3) . ?
C4 C3 1.401(4) . ?
C4 C5 1.405(4) . ?
C3 C2 1.446(4) . ?
C3 C8 1.397(4) . ?
C2 C1 1.560(3) . ?
C17 C16 1.468(4) . ?
C17 C18 1.409(4) . ?
C1 C15 1.531(4) . ?
C1 C9 1.520(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.507(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.447(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.371(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.395(4) . ?
C9 C10 1.383(4) . ?
C9 C14 1.401(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.348(5) . ?
C20 H20 0.9300 . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.417(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.355(7) . ?
C14 H14 0.9300 . ?
C14 C13 1.390(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.351(7) . ?
C13 H13 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C20 S1 C17 91.78(15) . . ?
O3 S2 C22 107.0(3) . . ?
O3 S2 C21 105.2(2) . . ?
C22 S2 C21 99.0(3) . . ?
C4 N1 H1 124.2 . . ?
C4 N1 C1 111.6(2) . . ?
C1 N1 H1 124.2 . . ?
N1 C4 C3 112.0(2) . . ?
N1 C4 C5 127.9(2) . . ?
C3 C4 C5 120.0(3) . . ?
C4 C3 C2 107.5(2) . . ?
C8 C3 C4 121.2(3) . . ?
C8 C3 C2 131.3(2) . . ?
O1 C2 C3 129.5(2) . . ?
O1 C2 C1 123.6(2) . . ?
C3 C2 C1 106.9(2) . . ?
C16 C17 S1 119.0(2) . . ?
C18 C17 S1 112.4(2) . . ?
C18 C17 C16 128.6(2) . . ?
N1 C1 C2 102.0(2) . . ?
N1 C1 C15 110.1(2) . . ?
N1 C1 C9 113.9(2) . . ?
C15 C1 C2 106.3(2) . . ?
C9 C1 C2 109.0(2) . . ?
C9 C1 C15 114.5(2) . . ?
C1 C15 H15A 108.6 . . ?
C1 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C1 114.5(2) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
O2 C16 C17 120.9(2) . . ?
O2 C16 C15 122.5(2) . . ?
C17 C16 C15 116.5(2) . . ?
C17 C18 H18 125.4 . . ?
C17 C18 C19 109.1(3) . . ?
C19 C18 H18 125.4 . . ?
C4 C5 H5 121.3 . . ?
C6 C5 C4 117.4(3) . . ?
C6 C5 H5 121.3 . . ?
C3 C8 H8 120.8 . . ?
C7 C8 C3 118.5(3) . . ?
C7 C8 H8 120.8 . . ?
C5 C6 H6 118.7 . . ?
C5 C6 C7 122.5(3) . . ?
C7 C6 H6 118.7 . . ?
C10 C9 C1 121.7(3) . . ?
C10 C9 C14 118.1(3) . . ?
C14 C9 C1 120.1(3) . . ?
C18 C19 H19 123.3 . . ?
C20 C19 C18 113.4(3) . . ?
C20 C19 H19 123.3 . . ?
S1 C20 H20 123.3 . . ?
C19 C20 S1 113.3(2) . . ?
C19 C20 H20 123.3 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.8 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.7(4) . . ?
C13 C14 H14 119.7 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
S2 C22 H22A 109.5 . . ?
S2 C22 H22B 109.5 . . ?
S2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S2 C21 H21A 109.5 . . ?
S2 C21 H21B 109.5 . . ?
S2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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 C17 C16 O2 1.5(4) . . . . ?
S1 C17 C16 C15 -176.18(19) . . . . ?
S1 C17 C18 C19 1.2(3) . . . . ?
O1 C2 C1 N1 -176.7(3) . . . . ?
O1 C2 C1 C15 -61.4(3) . . . . ?
O1 C2 C1 C9 62.5(3) . . . . ?
N1 C4 C3 C2 -0.5(3) . . . . ?
N1 C4 C3 C8 178.5(2) . . . . ?
N1 C4 C5 C6 -179.1(3) . . . . ?
N1 C1 C15 C16 -58.6(3) . . . . ?
N1 C1 C9 C10 -12.6(4) . . . . ?
N1 C1 C9 C14 171.4(3) . . . . ?
C4 N1 C1 C2 -2.4(3) . . . . ?
C4 N1 C1 C15 -114.9(3) . . . . ?
C4 N1 C1 C9 114.9(3) . . . . ?
C4 C3 C2 O1 177.6(3) . . . . ?
C4 C3 C2 C1 -1.1(3) . . . . ?
C4 C3 C8 C7 1.2(4) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C3 C2 C1 N1 2.1(3) . . . . ?
C3 C2 C1 C15 117.4(2) . . . . ?
C3 C2 C1 C9 -118.7(2) . . . . ?
C3 C8 C7 C6 -0.2(5) . . . . ?
C2 C3 C8 C7 179.8(3) . . . . ?
C2 C1 C15 C16 -168.3(2) . . . . ?
C2 C1 C9 C10 100.5(3) . . . . ?
C2 C1 C9 C14 -75.4(3) . . . . ?
C17 S1 C20 C19 -0.7(3) . . . . ?
C17 C18 C19 C20 -1.7(4) . . . . ?
C1 N1 C4 C3 2.0(3) . . . . ?
C1 N1 C4 C5 -177.9(3) . . . . ?
C1 C15 C16 O2 -9.3(4) . . . . ?
C1 C15 C16 C17 168.2(2) . . . . ?
C1 C9 C10 C11 -176.0(3) . . . . ?
C1 C9 C14 C13 176.9(3) . . . . ?
C15 C1 C9 C10 -140.6(3) . . . . ?
C15 C1 C9 C14 43.5(3) . . . . ?
C16 C17 C18 C19 -177.5(3) . . . . ?
C18 C17 C16 O2 -179.9(3) . . . . ?
C18 C17 C16 C15 2.4(4) . . . . ?
C18 C19 C20 S1 1.6(4) . . . . ?
C5 C4 C3 C2 179.4(2) . . . . ?
C5 C4 C3 C8 -1.7(4) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
C8 C3 C2 O1 -1.2(5) . . . . ?
C8 C3 C2 C1 -179.9(3) . . . . ?
C9 C1 C15 C16 71.3(3) . . . . ?
C9 C10 C11 C12 -1.3(6) . . . . ?
C9 C14 C13 C12 -0.4(6) . . . . ?
C20 S1 C17 C16 178.5(2) . . . . ?
C20 S1 C17 C18 -0.3(2) . . . . ?
C10 C9 C14 C13 0.8(5) . . . . ?
C10 C11 C12 C13 1.7(7) . . . . ?
C11 C12 C13 C14 -0.9(6) . . . . ?
C14 C9 C10 C11 0.0(5) . . . . ?

_olex2_date_sample_data_collection 2018-06-29
_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 1.182
_oxdiff_exptl_absorpt_empirical_full_min 0.855
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
