# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_engle389
_database_code_depnum_ccdc_archive 'CCDC 2149662'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;UC San Diego
United States of America
;
_audit_update_record             
;
2022-02-01 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2022-02-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 N O S'
_chemical_formula_sum            'C15 H15 N O S'
_chemical_formula_weight         257.34
_chemical_melting_point          ?
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.7788(18)
_cell_length_b                   5.6659(7)
_cell_length_c                   16.0675(19)
_cell_angle_alpha                90
_cell_angle_beta                 116.848(3)
_cell_angle_gamma                90
_cell_volume                     1281.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4386
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.6465
_exptl_absorpt_correction_T_min  0.6136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1101 before and 0.0408 after correction.
The Ratio of minimum to maximum transmission is 0.9349.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13350
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.029
_diffrn_reflns_theta_min         1.501
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2232
_reflns_number_total             2508
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.087
_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)+(0.0209P)²+1.8916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C)
;
_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 0.61974(3) 0.59943(9) 0.82815(3) 0.01428(14) Uani 1 1 d . . . . .
O1 O 0.45135(10) 0.7166(3) 0.93173(9) 0.0178(3) Uani 1 1 d . . . . .
N1 N 0.55874(11) 0.7492(3) 0.87491(11) 0.0147(4) Uani 1 1 d . . . . .
C1 C 0.61240(15) 0.9283(4) 0.94558(14) 0.0190(4) Uani 1 1 d . . . . .
H1A H 0.660395 0.850363 1.001459 0.029 Uiso 1 1 calc R U . . .
H1B H 0.568796 1.017609 0.961864 0.029 Uiso 1 1 calc R U . . .
H1C H 0.643713 1.036107 0.920463 0.029 Uiso 1 1 calc R U . . .
C2 C 0.47731(13) 0.6564(3) 0.87420(13) 0.0129(4) Uani 1 1 d . . . . .
C3 C 0.42116(13) 0.4804(4) 0.79966(13) 0.0133(4) Uani 1 1 d . . . . .
C4 C 0.39368(14) 0.5214(4) 0.70534(14) 0.0150(4) Uani 1 1 d . . . . .
H4 H 0.415276 0.658412 0.686571 0.018 Uiso 1 1 calc R U . . .
C5 C 0.33484(14) 0.3619(4) 0.63911(14) 0.0173(4) Uani 1 1 d . . . . .
H5 H 0.315627 0.391143 0.574852 0.021 Uiso 1 1 calc R U . . .
C6 C 0.30368(14) 0.1598(4) 0.66581(14) 0.0181(4) Uani 1 1 d . . . . .
H6 H 0.263481 0.050891 0.620021 0.022 Uiso 1 1 calc R U . . .
C7 C 0.33159(14) 0.1173(4) 0.75990(14) 0.0176(4) Uani 1 1 d . . . . .
H7 H 0.310812 -0.021299 0.778561 0.021 Uiso 1 1 calc R U . . .
C8 C 0.38975(13) 0.2775(4) 0.82638(14) 0.0155(4) Uani 1 1 d . . . . .
H8 H 0.408335 0.248840 0.890551 0.019 Uiso 1 1 calc R U . . .
C9 C 0.61335(13) 0.7901(4) 0.73811(13) 0.0139(4) Uani 1 1 d . . . . .
C10 C 0.56378(14) 1.0024(4) 0.71558(14) 0.0159(4) Uani 1 1 d . . . . .
H10 H 0.529813 1.051953 0.748524 0.019 Uiso 1 1 calc R U . . .
C11 C 0.56424(14) 1.1417(4) 0.64455(14) 0.0163(4) Uani 1 1 d . . . . .
H11 H 0.530753 1.287227 0.629950 0.020 Uiso 1 1 calc R U . . .
C12 C 0.61252(14) 1.0733(4) 0.59424(13) 0.0161(4) Uani 1 1 d . . . . .
C13 C 0.66036(14) 0.8576(4) 0.61701(14) 0.0167(4) Uani 1 1 d . . . . .
H13 H 0.692640 0.805558 0.582758 0.020 Uiso 1 1 calc R U . . .
C14 C 0.66190(14) 0.7175(4) 0.68831(13) 0.0152(4) Uani 1 1 d . . . . .
H14 H 0.695864 0.572661 0.703287 0.018 Uiso 1 1 calc R U . . .
C15 C 0.61456(15) 1.2275(4) 0.51880(14) 0.0204(5) Uani 1 1 d . . . . .
H15A H 0.556018 1.320798 0.490103 0.031 Uiso 1 1 calc R U . . .
H15B H 0.619573 1.128317 0.471255 0.031 Uiso 1 1 calc R U . . .
H15C H 0.669397 1.333742 0.545956 0.031 Uiso 1 1 calc R U . . .


_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 N1 1.6924(17) . ?
S1 C9 1.771(2) . ?
O1 C2 1.217(2) . ?
N1 C1 1.472(3) . ?
N1 C2 1.383(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.502(3) . ?
C3 C4 1.395(3) . ?
C3 C8 1.394(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(3) . ?
C9 C14 1.396(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(3) . ?
C12 C13 1.396(3) . ?
C12 C15 1.506(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
N1 S1 C9 102.88(9) . . ?
C1 N1 S1 116.34(13) . . ?
C2 N1 S1 121.20(14) . . ?
C2 N1 C1 118.48(16) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 121.13(18) . . ?
O1 C2 C3 120.82(18) . . ?
N1 C2 C3 118.05(16) . . ?
C4 C3 C2 122.54(18) . . ?
C8 C3 C2 117.76(17) . . ?
C8 C3 C4 119.52(18) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.85(19) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.58(19) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.73(19) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.89(19) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 H8 119.8 . . ?
C7 C8 C3 120.43(18) . . ?
C7 C8 H8 119.8 . . ?
C10 C9 S1 123.91(15) . . ?
C10 C9 C14 119.67(18) . . ?
C14 C9 S1 116.42(16) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.59(19) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.72(19) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C13 117.65(19) . . ?
C11 C12 C15 121.46(19) . . ?
C13 C12 C15 120.89(19) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.61(19) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.75(19) . . ?
C13 C14 H14 120.1 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 N1 C2 O1 155.10(15) . . . . ?
S1 N1 C2 C3 -25.5(2) . . . . ?
S1 C9 C10 C11 179.00(15) . . . . ?
S1 C9 C14 C13 -179.86(15) . . . . ?
O1 C2 C3 C4 129.1(2) . . . . ?
O1 C2 C3 C8 -45.8(3) . . . . ?
N1 S1 C9 C10 -2.64(19) . . . . ?
N1 S1 C9 C14 177.27(15) . . . . ?
N1 C2 C3 C4 -50.3(3) . . . . ?
N1 C2 C3 C8 134.74(19) . . . . ?
C1 N1 C2 O1 -1.6(3) . . . . ?
C1 N1 C2 C3 177.80(17) . . . . ?
C2 C3 C4 C5 -174.25(18) . . . . ?
C2 C3 C8 C7 175.10(18) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C3 -0.5(3) . . . . ?
C8 C3 C4 C5 0.6(3) . . . . ?
C9 S1 N1 C1 -84.18(16) . . . . ?
C9 S1 N1 C2 118.62(16) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C10 C11 C12 C15 -178.63(18) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C9 1.1(3) . . . . ?
C14 C9 C10 C11 -0.9(3) . . . . ?
C15 C12 C13 C14 177.76(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
####################################################################### 
# 
# 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_pn
_database_code_depnum_ccdc_archive 'CCDC 2154909'
loop_
_audit_author_name
_audit_author_address
'Jake Bailey'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2022-02-25 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2022-02-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 N2 O S'
_chemical_formula_sum            'C23 H26 N2 O S'
_chemical_formula_weight         378.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   7.7413(14)
_cell_length_b                   10.5757(19)
_cell_length_c                   25.507(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.727(5)
_cell_angle_gamma                90
_cell_volume                     2064.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.988
_cell_measurement_theta_min      2.514
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1174 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.7773.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19359
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.066
_diffrn_reflns_theta_min         1.615
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_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_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                7811
_reflns_number_total             8011
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'APEX2 v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.357
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 3468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         8011
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.072
_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)+(0.0904P)²+0.0712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1298
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.516(2)
 0.484(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C9A(H9A), C8A(H8A), C8(H8), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C13A(H13A,H13B), C13(H13C,H13D), C11(H11C,H11D)
3.c Aromatic/amide H refined with riding coordinates:
 N1A(H1A), C6A(H6A), C20A(H20A), C16A(H16A), C21A(H21A), C18A(H18A),
 C22A(H22A), C1A(H1AA), C17A(H17A), C5A(H5A), C2A(H2A), N1(H1), C6(H6),
 C22(H22), C16(H16), C2(H2), C1(H1B), C5(H5), C18(H18), C21(H21), C17(H17),
 C20(H20)
3.d Idealised Me refined as rotating group:
 C4A(H4AA,H4AB,H4AC), C10A(H10A,H10B,H10C), C12A(H12A,H12B,H12C), C4(H4A,H4B,
 H4C), C10(H10D,H10E,H10F), C12(H12D,H12E,H12F)
;
_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
S1A S 0.47894(16) 0.22784(13) 0.60914(5) 0.0204(3) Uani 1 1 d . . . . .
O1A O 0.6362(6) 0.2606(5) 0.74448(19) 0.0370(12) Uani 1 1 d . . . . .
N1A N 0.3533(6) 0.2154(4) 0.75122(17) 0.0193(10) Uani 1 1 d . . . . .
H1A H 0.245189 0.236482 0.738314 0.023 Uiso 1 1 calc R U . . .
N2A N 0.0712(6) 0.0771(4) 0.76052(17) 0.0176(10) Uani 1 1 d . . . . .
C9A C 0.4843(9) 0.4930(5) 0.6073(2) 0.0215(11) Uani 1 1 d . . . . .
H9A H 0.508941 0.569674 0.630228 0.026 Uiso 1 1 calc R U . . .
C6A C 0.6874(10) 0.1174(5) 0.5454(2) 0.0246(14) Uani 1 1 d . . . . .
H6A H 0.584271 0.117192 0.519918 0.029 Uiso 1 1 calc R U . . .
C19A C 0.2276(8) -0.0508(5) 0.8324(2) 0.0218(12) Uani 1 1 d . . . . .
C20A C 0.0746(10) -0.1201(5) 0.8329(2) 0.0258(13) Uani 1 1 d . . . . .
H20A H 0.075194 -0.189261 0.856708 0.031 Uiso 1 1 calc R U . . .
C16A C 0.5240(9) 0.0953(6) 0.8226(2) 0.0268(13) Uani 1 1 d . . . . .
H16A H 0.625914 0.142201 0.818732 0.032 Uiso 1 1 calc R U . . .
C14A C 0.4799(7) 0.2790(6) 0.7311(2) 0.0201(11) Uani 1 1 d . . . . .
C7A C 0.6833(7) 0.1745(5) 0.59466(19) 0.0155(10) Uani 1 1 d . . . . .
C23A C 0.2207(8) 0.0478(5) 0.7936(2) 0.0194(11) Uani 1 1 d . . . . .
C15A C 0.3718(7) 0.1201(5) 0.7901(2) 0.0159(11) Uani 1 1 d . . . . .
C21A C -0.0753(9) -0.0908(6) 0.8001(3) 0.0301(14) Uani 1 1 d . . . . .
H21A H -0.179609 -0.137416 0.801125 0.036 Uiso 1 1 calc R U . . .
C8A C 0.5231(8) 0.3791(5) 0.64430(19) 0.0166(11) Uani 1 1 d . . . . .
H8A H 0.649290 0.381505 0.660218 0.020 Uiso 1 1 calc R U . . .
C18A C 0.3881(10) -0.0733(6) 0.8661(2) 0.0294(15) Uani 1 1 d . . . . .
H18A H 0.395677 -0.139768 0.891364 0.035 Uiso 1 1 calc R U . . .
C11A C 0.2920(9) 0.5026(6) 0.5823(2) 0.0276(13) Uani 1 1 d . . . . .
H11A H 0.262302 0.428902 0.558772 0.033 Uiso 1 1 calc R U . . .
H11B H 0.218450 0.498329 0.610844 0.033 Uiso 1 1 calc R U . . .
C4A C 1.1496(8) -0.0016(6) 0.5549(3) 0.0274(14) Uani 1 1 d . . . . .
H4AA H 1.208497 0.056266 0.533307 0.041 Uiso 1 1 calc R U . . .
H4AB H 1.117193 -0.079185 0.534777 0.041 Uiso 1 1 calc R U . . .
H4AC H 1.228539 -0.022349 0.587501 0.041 Uiso 1 1 calc R U . . .
C22A C -0.0715(9) 0.0111(6) 0.7644(2) 0.0260(13) Uani 1 1 d . . . . .
H22A H -0.176713 0.033237 0.742022 0.031 Uiso 1 1 calc R U . . .
C13A C 0.4125(8) 0.3780(5) 0.6894(2) 0.0183(11) Uani 1 1 d . . . . .
H13A H 0.416496 0.462611 0.706146 0.022 Uiso 1 1 calc R U . . .
H13B H 0.289335 0.359265 0.674695 0.022 Uiso 1 1 calc R U . . .
C3A C 0.9907(8) 0.0596(5) 0.5684(2) 0.0210(12) Uani 1 1 d . . . . .
C1A C 0.8361(8) 0.1753(6) 0.6309(2) 0.0224(13) Uani 1 1 d . . . . .
H1AA H 0.837846 0.212612 0.664834 0.027 Uiso 1 1 calc R U . . .
C10A C 0.6112(10) 0.4995(7) 0.5662(3) 0.0334(16) Uani 1 1 d . . . . .
H10A H 0.597201 0.423623 0.543901 0.050 Uiso 1 1 calc R U . . .
H10B H 0.731667 0.504116 0.584669 0.050 Uiso 1 1 calc R U . . .
H10C H 0.585264 0.574690 0.543996 0.050 Uiso 1 1 calc R U . . .
C17A C 0.5330(10) 0.0001(7) 0.8626(3) 0.0401(18) Uani 1 1 d . . . . .
H17A H 0.638074 -0.012622 0.886546 0.048 Uiso 1 1 calc R U . . .
C5A C 0.8367(8) 0.0612(5) 0.5327(2) 0.0192(11) Uani 1 1 d . . . . .
H5A H 0.833811 0.023007 0.498899 0.023 Uiso 1 1 calc R U . . .
C12A C 0.2477(13) 0.6230(8) 0.5505(3) 0.045(2) Uani 1 1 d . . . . .
H12A H 0.302129 0.620335 0.518251 0.067 Uiso 1 1 calc R U . . .
H12B H 0.291910 0.696339 0.571947 0.067 Uiso 1 1 calc R U . . .
H12C H 0.120658 0.629953 0.540830 0.067 Uiso 1 1 calc R U . . .
C2A C 0.9877(8) 0.1208(6) 0.6172(2) 0.0227(13) Uani 1 1 d . . . . .
H2A H 1.092677 0.125235 0.641881 0.027 Uiso 1 1 calc R U . . .
S1 S 0.59855(18) 0.47246(13) 0.38858(6) 0.0226(3) Uani 1 1 d . . . A 1
O1 O 0.6070(9) 0.5504(7) 0.2472(2) 0.069(2) Uani 1 1 d . . . A 1
N2 N 0.0573(6) 0.3238(4) 0.24514(17) 0.0180(10) Uani 1 1 d . . . A 1
N1 N 0.3441(6) 0.4653(4) 0.25425(18) 0.0188(10) Uani 1 1 d . . . A 1
H1 H 0.254273 0.472501 0.271445 0.023 Uiso 1 1 calc R U . A 1
C6 C 0.8664(8) 0.3696(5) 0.4560(2) 0.0190(12) Uani 1 1 d . . . A 1
H6 H 0.786769 0.370622 0.480942 0.023 Uiso 1 1 calc R U . A 1
C8 C 0.6139(8) 0.6278(5) 0.3579(2) 0.0193(11) Uani 1 1 d . . . A 1
H8 H 0.722632 0.629200 0.341142 0.023 Uiso 1 1 calc R U . A 1
C22 C -0.0839(8) 0.2529(6) 0.2418(2) 0.0239(12) Uani 1 1 d . . . A 1
H22 H -0.166119 0.271448 0.264835 0.029 Uiso 1 1 calc R U . A 1
C15 C 0.3311(8) 0.3703(5) 0.2155(2) 0.0191(11) Uani 1 1 d . . . A 1
C23 C 0.1758(7) 0.2949(5) 0.2122(2) 0.0170(11) Uani 1 1 d . . . A 1
C16 C 0.4532(8) 0.3450(6) 0.1824(2) 0.0277(14) Uani 1 1 d . . . A 1
H16 H 0.556572 0.394358 0.184606 0.033 Uiso 1 1 calc R U . A 1
C13 C 0.4555(9) 0.6356(5) 0.3131(2) 0.0214(12) Uani 1 1 d . . . A 1
H13C H 0.347583 0.613601 0.327518 0.026 Uiso 1 1 calc R U . A 1
H13D H 0.443189 0.723343 0.299476 0.026 Uiso 1 1 calc R U . A 1
C3 C 1.1493(7) 0.3168(5) 0.4347(2) 0.0180(11) Uani 1 1 d . . . A 1
C9 C 0.6231(8) 0.7389(5) 0.3972(2) 0.0216(12) Uani 1 1 d . . . A 1
H9 H 0.630636 0.818162 0.376363 0.026 Uiso 1 1 calc R U . A 1
C2 C 1.1029(8) 0.3694(5) 0.3853(2) 0.0226(11) Uani 1 1 d . . . A 1
H2 H 1.185425 0.370802 0.361321 0.027 Uiso 1 1 calc R U . A 1
C7 C 0.8173(8) 0.4220(5) 0.4056(2) 0.0200(12) Uani 1 1 d . . . A 1
C11 C 0.4596(10) 0.7497(6) 0.4239(2) 0.0293(14) Uani 1 1 d . . . A 1
H11C H 0.355874 0.754895 0.396053 0.035 Uiso 1 1 calc R U . A 1
H11D H 0.448445 0.671833 0.444671 0.035 Uiso 1 1 calc R U . A 1
C1 C 0.9379(8) 0.4206(5) 0.3698(2) 0.0196(12) Uani 1 1 d . . . A 1
H1B H 0.906952 0.454468 0.335198 0.023 Uiso 1 1 calc R U . A 1
C5 C 1.0268(8) 0.3174(6) 0.4695(2) 0.0223(12) Uani 1 1 d . . . A 1
H5 H 1.056588 0.280233 0.503628 0.027 Uiso 1 1 calc R U . A 1
C18 C 0.2783(10) 0.1701(6) 0.1420(2) 0.0319(15) Uani 1 1 d . . . A 1
H18 H 0.263943 0.102125 0.117386 0.038 Uiso 1 1 calc R U . A 1
C21 C -0.1203(9) 0.1516(6) 0.2062(2) 0.0281(14) Uani 1 1 d . . . A 1
H21 H -0.226099 0.105182 0.204618 0.034 Uiso 1 1 calc R U . A 1
C19 C 0.1502(8) 0.1934(5) 0.1752(2) 0.0226(12) Uani 1 1 d . . . A 1
C17 C 0.4226(9) 0.2462(7) 0.1458(2) 0.0314(15) Uani 1 1 d . . . A 1
H17 H 0.505459 0.231213 0.122622 0.038 Uiso 1 1 calc R U . A 1
C4 C 1.3232(8) 0.2536(7) 0.4497(3) 0.0268(14) Uani 1 1 d . . . A 1
H4A H 1.344323 0.195722 0.421392 0.040 Uiso 1 1 calc R U . A 1
H4B H 1.323488 0.206023 0.482715 0.040 Uiso 1 1 calc R U . A 1
H4C H 1.415437 0.317875 0.454936 0.040 Uiso 1 1 calc R U . A 1
C14 C 0.4772(8) 0.5475(6) 0.2686(2) 0.0246(13) Uani 1 1 d . . . A 1
C20 C -0.0018(10) 0.1211(5) 0.1742(2) 0.0300(14) Uani 1 1 d . . . A 1
H20 H -0.021949 0.050581 0.151034 0.036 Uiso 1 1 calc R U . A 1
C10 C 0.7920(9) 0.7311(7) 0.4382(3) 0.0304(15) Uani 1 1 d . . . A 1
H10D H 0.814122 0.813131 0.455826 0.046 Uiso 1 1 calc R U . A 1
H10E H 0.890736 0.708917 0.420096 0.046 Uiso 1 1 calc R U . A 1
H10F H 0.778120 0.666263 0.464733 0.046 Uiso 1 1 calc R U . A 1
C12 C 0.4593(16) 0.8631(8) 0.4605(3) 0.053(2) Uani 1 1 d . . . A 1
H12D H 0.487402 0.939705 0.441847 0.079 Uiso 1 1 calc R U . A 1
H12E H 0.546781 0.850683 0.492087 0.079 Uiso 1 1 calc R U . A 1
H12F H 0.343417 0.872182 0.471092 0.079 Uiso 1 1 calc R U . A 1


_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
S1A C7A 1.770(5) . ?
S1A C8A 1.840(5) . ?
O1A C14A 1.222(7) . ?
N1A H1A 0.8800 . ?
N1A C14A 1.352(7) . ?
N1A C15A 1.405(7) . ?
N2A C23A 1.360(8) . ?
N2A C22A 1.323(8) . ?
C9A H9A 1.0000 . ?
C9A C8A 1.531(7) . ?
C9A C11A 1.532(10) . ?
C9A C10A 1.543(9) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.398(8) . ?
C6A C5A 1.381(9) . ?
C19A C20A 1.394(9) . ?
C19A C23A 1.432(8) . ?
C19A C18A 1.419(9) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.360(10) . ?
C16A H16A 0.9500 . ?
C16A C15A 1.360(8) . ?
C16A C17A 1.426(8) . ?
C14A C13A 1.528(7) . ?
C7A C1A 1.387(8) . ?
C23A C15A 1.412(8) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.414(9) . ?
C8A H8A 1.0000 . ?
C8A C13A 1.534(7) . ?
C18A H18A 0.9500 . ?
C18A C17A 1.378(10) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C11A C12A 1.521(9) . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C4A C3A 1.477(9) . ?
C22A H22A 0.9500 . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C3A C5A 1.386(8) . ?
C3A C2A 1.406(8) . ?
C1A H1AA 0.9500 . ?
C1A C2A 1.398(9) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C17A H17A 0.9500 . ?
C5A H5A 0.9500 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C2A H2A 0.9500 . ?
S1 C8 1.832(6) . ?
S1 C7 1.766(6) . ?
O1 C14 1.215(8) . ?
N2 C22 1.317(7) . ?
N2 C23 1.369(7) . ?
N1 H1 0.8800 . ?
N1 C15 1.401(7) . ?
N1 C14 1.355(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.400(8) . ?
C6 C5 1.355(9) . ?
C8 H8 1.0000 . ?
C8 C13 1.546(8) . ?
C8 C9 1.540(7) . ?
C22 H22 0.9500 . ?
C22 C21 1.405(9) . ?
C15 C23 1.435(8) . ?
C15 C16 1.385(8) . ?
C23 C19 1.424(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.398(9) . ?
C13 H13C 0.9900 . ?
C13 H13D 0.9900 . ?
C13 C14 1.497(8) . ?
C3 C2 1.373(8) . ?
C3 C5 1.395(8) . ?
C3 C4 1.500(8) . ?
C9 H9 1.0000 . ?
C9 C11 1.530(9) . ?
C9 C10 1.547(9) . ?
C2 H2 0.9500 . ?
C2 C1 1.389(9) . ?
C7 C1 1.400(8) . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C11 C12 1.519(9) . ?
C1 H1B 0.9500 . ?
C5 H5 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.419(9) . ?
C18 C17 1.368(10) . ?
C21 H21 0.9500 . ?
C21 C20 1.357(10) . ?
C19 C20 1.400(9) . ?
C17 H17 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C20 H20 0.9500 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10F 0.9800 . ?
C12 H12D 0.9800 . ?
C12 H12E 0.9800 . ?
C12 H12F 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
C7A S1A C8A 105.8(3) . . ?
C14A N1A H1A 115.8 . . ?
C14A N1A C15A 128.4(5) . . ?
C15A N1A H1A 115.8 . . ?
C22A N2A C23A 118.4(5) . . ?
C8A C9A H9A 106.1 . . ?
C8A C9A C11A 113.3(5) . . ?
C8A C9A C10A 111.6(5) . . ?
C11A C9A H9A 106.1 . . ?
C11A C9A C10A 113.1(5) . . ?
C10A C9A H9A 106.1 . . ?
C7A C6A H6A 119.0 . . ?
C5A C6A H6A 119.0 . . ?
C5A C6A C7A 122.0(6) . . ?
C20A C19A C23A 116.5(5) . . ?
C20A C19A C18A 124.9(5) . . ?
C18A C19A C23A 118.5(5) . . ?
C19A C20A H20A 119.3 . . ?
C21A C20A C19A 121.4(5) . . ?
C21A C20A H20A 119.3 . . ?
C15A C16A H16A 119.5 . . ?
C15A C16A C17A 121.1(6) . . ?
C17A C16A H16A 119.5 . . ?
O1A C14A N1A 124.0(5) . . ?
O1A C14A C13A 121.5(5) . . ?
N1A C14A C13A 114.5(5) . . ?
C6A C7A S1A 117.9(5) . . ?
C1A C7A S1A 123.9(4) . . ?
C1A C7A C6A 117.9(5) . . ?
N2A C23A C19A 122.2(5) . . ?
N2A C23A C15A 118.2(5) . . ?
C15A C23A C19A 119.6(5) . . ?
N1A C15A C23A 115.9(5) . . ?
C16A C15A N1A 123.7(5) . . ?
C16A C15A C23A 120.4(5) . . ?
C20A C21A H21A 120.9 . . ?
C20A C21A C22A 118.1(6) . . ?
C22A C21A H21A 120.9 . . ?
S1A C8A H8A 108.5 . . ?
C9A C8A S1A 112.3(3) . . ?
C9A C8A H8A 108.5 . . ?
C9A C8A C13A 112.8(5) . . ?
C13A C8A S1A 106.0(4) . . ?
C13A C8A H8A 108.5 . . ?
C19A C18A H18A 119.6 . . ?
C17A C18A C19A 120.8(6) . . ?
C17A C18A H18A 119.6 . . ?
C9A C11A H11A 108.8 . . ?
C9A C11A H11B 108.8 . . ?
H11A C11A H11B 107.7 . . ?
C12A C11A C9A 113.8(6) . . ?
C12A C11A H11A 108.8 . . ?
C12A C11A H11B 108.8 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C3A C4A H4AA 109.5 . . ?
C3A C4A H4AB 109.5 . . ?
C3A C4A H4AC 109.5 . . ?
N2A C22A C21A 123.3(6) . . ?
N2A C22A H22A 118.4 . . ?
C21A C22A H22A 118.4 . . ?
C14A C13A C8A 110.9(5) . . ?
C14A C13A H13A 109.5 . . ?
C14A C13A H13B 109.5 . . ?
C8A C13A H13A 109.5 . . ?
C8A C13A H13B 109.5 . . ?
H13A C13A H13B 108.0 . . ?
C5A C3A C4A 121.0(5) . . ?
C5A C3A C2A 116.6(6) . . ?
C2A C3A C4A 122.4(5) . . ?
C7A C1A H1AA 120.1 . . ?
C7A C1A C2A 119.7(5) . . ?
C2A C1A H1AA 120.1 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C16A C17A H17A 120.3 . . ?
C18A C17A C16A 119.4(7) . . ?
C18A C17A H17A 120.3 . . ?
C6A C5A C3A 121.2(5) . . ?
C6A C5A H5A 119.4 . . ?
C3A C5A H5A 119.4 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C3A C2A H2A 118.8 . . ?
C1A C2A C3A 122.5(5) . . ?
C1A C2A H2A 118.8 . . ?
C7 S1 C8 104.7(3) . . ?
C22 N2 C23 117.4(5) . . ?
C15 N1 H1 115.8 . . ?
C14 N1 H1 115.8 . . ?
C14 N1 C15 128.4(5) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.4(5) . . ?
S1 C8 H8 108.0 . . ?
C13 C8 S1 105.5(4) . . ?
C13 C8 H8 108.0 . . ?
C9 C8 S1 113.9(4) . . ?
C9 C8 H8 108.0 . . ?
C9 C8 C13 113.2(5) . . ?
N2 C22 H22 118.0 . . ?
N2 C22 C21 124.0(6) . . ?
C21 C22 H22 118.0 . . ?
N1 C15 C23 114.2(5) . . ?
C16 C15 N1 125.8(5) . . ?
C16 C15 C23 120.0(5) . . ?
N2 C23 C15 118.3(5) . . ?
N2 C23 C19 122.5(5) . . ?
C19 C23 C15 119.3(5) . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.3(6) . . ?
C17 C16 H16 120.3 . . ?
C8 C13 H13C 109.4 . . ?
C8 C13 H13D 109.4 . . ?
H13C C13 H13D 108.0 . . ?
C14 C13 C8 111.0(6) . . ?
C14 C13 H13C 109.4 . . ?
C14 C13 H13D 109.4 . . ?
C2 C3 C5 118.3(5) . . ?
C2 C3 C4 121.0(5) . . ?
C5 C3 C4 120.7(5) . . ?
C8 C9 H9 107.0 . . ?
C8 C9 C10 110.5(5) . . ?
C11 C9 C8 112.8(5) . . ?
C11 C9 H9 107.0 . . ?
C11 C9 C10 112.0(5) . . ?
C10 C9 H9 107.0 . . ?
C3 C2 H2 119.3 . . ?
C3 C2 C1 121.3(5) . . ?
C1 C2 H2 119.3 . . ?
C6 C7 S1 117.5(4) . . ?
C6 C7 C1 118.7(5) . . ?
C1 C7 S1 123.5(4) . . ?
C9 C11 H11C 108.7 . . ?
C9 C11 H11D 108.7 . . ?
H11C C11 H11D 107.6 . . ?
C12 C11 C9 114.3(7) . . ?
C12 C11 H11C 108.7 . . ?
C12 C11 H11D 108.7 . . ?
C2 C1 C7 119.6(5) . . ?
C2 C1 H1B 120.2 . . ?
C7 C1 H1B 120.2 . . ?
C6 C5 C3 121.7(5) . . ?
C6 C5 H5 119.2 . . ?
C3 C5 H5 119.2 . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.5(5) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 C22 118.8(6) . . ?
C20 C21 H21 120.6 . . ?
C18 C19 C23 119.2(5) . . ?
C20 C19 C23 117.1(5) . . ?
C20 C19 C18 123.8(5) . . ?
C16 C17 H17 118.6 . . ?
C18 C17 C16 122.8(6) . . ?
C18 C17 H17 118.6 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C14 N1 122.8(5) . . ?
O1 C14 C13 121.4(6) . . ?
N1 C14 C13 115.9(5) . . ?
C21 C20 C19 120.2(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C9 C10 H10D 109.5 . . ?
C9 C10 H10E 109.5 . . ?
C9 C10 H10F 109.5 . . ?
H10D C10 H10E 109.5 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
C11 C12 H12D 109.5 . . ?
C11 C12 H12E 109.5 . . ?
C11 C12 H12F 109.5 . . ?
H12D C12 H12E 109.5 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 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
S1A C7A C1A C2A 174.3(4) . . . . ?
S1A C8A C13A C14A 68.0(5) . . . . ?
O1A C14A C13A C8A 39.2(8) . . . . ?
N1A C14A C13A C8A -140.8(5) . . . . ?
N2A C23A C15A N1A -1.2(7) . . . . ?
N2A C23A C15A C16A 179.3(5) . . . . ?
C9A C8A C13A C14A -168.7(5) . . . . ?
C6A C7A C1A C2A 0.5(8) . . . . ?
C19A C20A C21A C22A 1.2(9) . . . . ?
C19A C23A C15A N1A -179.5(5) . . . . ?
C19A C23A C15A C16A 1.0(8) . . . . ?
C19A C18A C17A C16A -3.4(10) . . . . ?
C20A C19A C23A N2A 3.1(8) . . . . ?
C20A C19A C23A C15A -178.7(5) . . . . ?
C20A C19A C18A C17A 179.8(6) . . . . ?
C20A C21A C22A N2A 1.6(9) . . . . ?
C14A N1A C15A C16A 15.4(9) . . . . ?
C14A N1A C15A C23A -164.0(5) . . . . ?
C7A S1A C8A C9A 97.5(5) . . . . ?
C7A S1A C8A C13A -138.9(4) . . . . ?
C7A C6A C5A C3A -0.3(9) . . . . ?
C7A C1A C2A C3A -2.7(9) . . . . ?
C23A N2A C22A C21A -1.9(9) . . . . ?
C23A C19A C20A C21A -3.3(8) . . . . ?
C23A C19A C18A C17A 1.7(9) . . . . ?
C15A N1A C14A O1A 0.5(10) . . . . ?
C15A N1A C14A C13A -179.5(5) . . . . ?
C15A C16A C17A C18A 4.0(10) . . . . ?
C8A S1A C7A C6A -140.7(4) . . . . ?
C8A S1A C7A C1A 45.6(5) . . . . ?
C8A C9A C11A C12A 173.5(5) . . . . ?
C18A C19A C20A C21A 178.5(6) . . . . ?
C18A C19A C23A N2A -178.6(5) . . . . ?
C18A C19A C23A C15A -0.4(8) . . . . ?
C11A C9A C8A S1A 62.5(6) . . . . ?
C11A C9A C8A C13A -57.2(6) . . . . ?
C4A C3A C5A C6A 179.5(5) . . . . ?
C4A C3A C2A C1A -177.9(5) . . . . ?
C22A N2A C23A C19A -0.5(8) . . . . ?
C22A N2A C23A C15A -178.8(5) . . . . ?
C10A C9A C8A S1A -66.6(6) . . . . ?
C10A C9A C8A C13A 173.7(5) . . . . ?
C10A C9A C11A C12A -58.2(7) . . . . ?
C17A C16A C15A N1A 177.8(6) . . . . ?
C17A C16A C15A C23A -2.8(9) . . . . ?
C5A C6A C7A S1A -173.1(4) . . . . ?
C5A C6A C7A C1A 1.0(8) . . . . ?
C5A C3A C2A C1A 3.2(8) . . . . ?
C2A C3A C5A C6A -1.7(8) . . . . ?
S1 C8 C13 C14 -69.9(5) . . . . ?
S1 C8 C9 C11 -62.3(6) . . . . ?
S1 C8 C9 C10 64.0(6) . . . . ?
S1 C7 C1 C2 -174.6(4) . . . . ?
N2 C22 C21 C20 2.1(9) . . . . ?
N2 C23 C19 C18 179.4(5) . . . . ?
N2 C23 C19 C20 -1.2(8) . . . . ?
N1 C15 C23 N2 1.5(7) . . . . ?
N1 C15 C23 C19 -178.5(5) . . . . ?
N1 C15 C16 C17 179.6(6) . . . . ?
C6 C7 C1 C2 -0.9(8) . . . . ?
C8 S1 C7 C6 134.8(5) . . . . ?
C8 S1 C7 C1 -51.5(6) . . . . ?
C8 C13 C14 O1 -53.7(9) . . . . ?
C8 C13 C14 N1 126.0(6) . . . . ?
C8 C9 C11 C12 -176.4(6) . . . . ?
C22 N2 C23 C15 -179.5(5) . . . . ?
C22 N2 C23 C19 0.5(8) . . . . ?
C22 C21 C20 C19 -2.8(9) . . . . ?
C15 N1 C14 O1 2.0(11) . . . . ?
C15 N1 C14 C13 -177.8(5) . . . . ?
C15 C23 C19 C18 -0.6(8) . . . . ?
C15 C23 C19 C20 178.8(5) . . . . ?
C15 C16 C17 C18 -1.8(10) . . . . ?
C23 N2 C22 C21 -0.9(8) . . . . ?
C23 C15 C16 C17 0.4(9) . . . . ?
C23 C19 C20 C21 2.4(9) . . . . ?
C16 C15 C23 N2 -179.2(5) . . . . ?
C16 C15 C23 C19 0.8(8) . . . . ?
C13 C8 C9 C11 58.3(6) . . . . ?
C13 C8 C9 C10 -175.4(5) . . . . ?
C3 C2 C1 C7 1.8(9) . . . . ?
C9 C8 C13 C14 164.9(5) . . . . ?
C2 C3 C5 C6 -0.9(9) . . . . ?
C7 S1 C8 C13 143.9(4) . . . . ?
C7 S1 C8 C9 -91.3(5) . . . . ?
C7 C6 C5 C3 1.7(9) . . . . ?
C5 C6 C7 S1 173.3(5) . . . . ?
C5 C6 C7 C1 -0.8(8) . . . . ?
C5 C3 C2 C1 -0.9(8) . . . . ?
C18 C19 C20 C21 -178.3(6) . . . . ?
C19 C18 C17 C16 2.0(10) . . . . ?
C17 C18 C19 C23 -0.7(9) . . . . ?
C17 C18 C19 C20 179.9(6) . . . . ?
C4 C3 C2 C1 175.7(5) . . . . ?
C4 C3 C5 C6 -177.4(6) . . . . ?
C14 N1 C15 C23 176.7(5) . . . . ?
C14 N1 C15 C16 -2.5(9) . . . . ?
C10 C9 C11 C12 58.1(7) . . . . ?

# start Validation Reply Form
_vrf_PLAT094_pn                  
;
PROBLEM: Ratio of Maximum / Minimum Residual Density .... 4.63 Report
RESPONSE: The measured crystal was a pseudomerohedral twin. There is excess 
residual density near H17 that could not be modeled. 
;
# end Validation Reply Form

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.516(2)
2 0.484(2)
