# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_s
_database_code_depnum_ccdc_archive 'CCDC 2209733'
loop_
_audit_author_name
_audit_author_address
'Xiaolin Zhu'
;Shaanxi Normal University
China
;
_audit_update_record             
;
2022-09-27 deposited with the CCDC.	2023-08-03 downloaded from the CCDC.
;
_audit_creation_date             2022-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N O2'
_chemical_formula_sum            'C18 H19 N O2'
_chemical_formula_weight         281.34
_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 0.0181 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'

_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                   11.2317(5)
_cell_length_b                   11.5042(5)
_cell_length_c                   11.6690(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1507.77(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    153.00
_cell_measurement_theta_max      68.177
_cell_measurement_theta_min      3.842
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.740
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0655 before and 0.0397 after correction.
The Ratio of minimum to maximum transmission is 0.9205.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20678
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.172
_diffrn_reflns_theta_min         7.890
_diffrn_ambient_temperature      153.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2695
_reflns_number_total             2699
_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       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details 
;
 Flack x determined using 1135 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2699
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.075
_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)+(0.0313P)²+0.2665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0668
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C14(H14), C16(H16)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
2.e :
 C11(H11)
;
_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
O1 O 0.74914(12) 0.80260(10) 0.81407(10) 0.0368(3) Uani 1 1 d . . . . .
O2 O 0.49292(11) 0.59579(10) 0.63609(9) 0.0335(3) Uani 1 1 d . . . . .
N1 N 0.64114(12) 0.72902(12) 0.61436(11) 0.0257(3) Uani 1 1 d . . . . .
C1 C 0.62513(13) 0.76523(13) 0.49975(14) 0.0243(3) Uani 1 1 d . . . . .
C4 C 0.52624(14) 0.76738(14) 0.31713(14) 0.0288(3) Uani 1 1 d . . . . .
H4 H 0.464229 0.739780 0.268903 0.035 Uiso 1 1 calc R U . . .
C6 C 0.53462(14) 0.72592(15) 0.42870(13) 0.0276(3) Uani 1 1 d . . . . .
H6 H 0.478520 0.670802 0.456259 0.033 Uiso 1 1 calc R U . . .
C8 C 0.57543(13) 0.65205(13) 0.67597(13) 0.0231(3) Uani 1 1 d . . . . .
C10 C 0.60685(14) 0.84851(14) 0.27461(13) 0.0263(3) Uani 1 1 d . . . . .
C12 C 0.59746(15) 0.89014(14) 0.15869(14) 0.0304(4) Uani 1 1 d . . . . .
C14 C 0.70581(15) 0.84669(16) 0.45752(14) 0.0332(4) Uani 1 1 d . . . . .
H14 H 0.767825 0.874169 0.505793 0.040 Uiso 1 1 calc R U . . .
C16 C 0.69725(15) 0.88820(16) 0.34674(15) 0.0337(4) Uani 1 1 d . . . . .
H16 H 0.752999 0.943870 0.319613 0.040 Uiso 1 1 calc R U . . .
C18 C 0.61211(14) 0.63592(13) 0.80009(12) 0.0237(3) Uani 1 1 d . . . . .
C9 C 0.71002(14) 0.71219(14) 0.85153(13) 0.0267(3) Uani 1 1 d . . . . .
C5 C 0.75154(16) 0.65131(16) 0.95983(14) 0.0338(4) Uani 1 1 d . . . . .
H5A H 0.736867 0.699690 1.028557 0.041 Uiso 1 1 calc R U . . .
H5B H 0.837253 0.631678 0.955746 0.041 Uiso 1 1 calc R U . . .
C11 C 0.58866(17) 0.92369(15) 0.06242(14) 0.0346(4) Uani 1 1 d . . . . .
H11 H 0.581638 0.950423 -0.014311 0.042 Uiso 1 1 calc R U . . .
C3 C 0.50713(15) 0.64968(17) 0.88697(14) 0.0331(4) Uani 1 1 d . . . . .
H3A H 0.494130 0.732466 0.906475 0.040 Uiso 1 1 calc R U . . .
H3B H 0.432496 0.617128 0.855228 0.040 Uiso 1 1 calc R U . . .
C13 C 0.67426(17) 0.54170(15) 0.96063(14) 0.0336(4) Uani 1 1 d . . . . .
H13 H 0.706899 0.476659 1.008006 0.040 Uiso 1 1 calc R U . . .
C7 C 0.66152(17) 0.51279(14) 0.83064(14) 0.0308(4) Uani 1 1 d . . . . .
C15 C 0.7794(2) 0.48724(18) 0.77125(16) 0.0446(5) Uani 1 1 d . . . . .
H15A H 0.764947 0.470694 0.690049 0.067 Uiso 1 1 calc R U . . .
H15B H 0.817148 0.419726 0.807348 0.067 Uiso 1 1 calc R U . . .
H15C H 0.831984 0.554868 0.778132 0.067 Uiso 1 1 calc R U . . .
C2 C 0.54865(18) 0.57963(18) 0.99394(15) 0.0393(4) Uani 1 1 d . . . . .
H2A H 0.549662 0.629089 1.063363 0.047 Uiso 1 1 calc R U . . .
H2B H 0.496529 0.511654 1.007723 0.047 Uiso 1 1 calc R U . . .
C17 C 0.5757(2) 0.41292(16) 0.80767(16) 0.0484(5) Uani 1 1 d . . . . .
H17A H 0.496632 0.433072 0.837105 0.073 Uiso 1 1 calc R U . . .
H17B H 0.604459 0.342605 0.846162 0.073 Uiso 1 1 calc R U . . .
H17C H 0.570808 0.398842 0.724979 0.073 Uiso 1 1 calc R U . . .
H1 H 0.6957(19) 0.7689(19) 0.6567(17) 0.036(5) Uiso 1 1 d . . . . .


_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
O1 C9 1.211(2) . ?
O2 C8 1.2224(19) . ?
N1 C1 1.412(2) . ?
N1 C8 1.359(2) . ?
N1 H1 0.91(2) . ?
C1 C6 1.388(2) . ?
C1 C14 1.394(2) . ?
C4 H4 0.9500 . ?
C4 C6 1.390(2) . ?
C4 C10 1.392(2) . ?
C6 H6 0.9500 . ?
C8 C18 1.517(2) . ?
C10 C12 1.439(2) . ?
C10 C16 1.396(2) . ?
C12 C11 1.192(2) . ?
C14 H14 0.9500 . ?
C14 C16 1.381(2) . ?
C16 H16 0.9500 . ?
C18 C9 1.530(2) . ?
C18 C3 1.563(2) . ?
C18 C7 1.563(2) . ?
C9 C5 1.518(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C13 1.531(3) . ?
C11 H11 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.557(2) . ?
C13 H13 1.0000 . ?
C13 C7 1.559(2) . ?
C13 C2 1.527(3) . ?
C7 C15 1.523(3) . ?
C7 C17 1.523(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C1 N1 H1 116.8(13) . . ?
C8 N1 C1 128.62(14) . . ?
C8 N1 H1 114.0(12) . . ?
C6 C1 N1 124.27(14) . . ?
C6 C1 C14 118.96(14) . . ?
C14 C1 N1 116.77(14) . . ?
C6 C4 H4 119.3 . . ?
C6 C4 C10 121.33(15) . . ?
C10 C4 H4 119.3 . . ?
C1 C6 C4 119.84(14) . . ?
C1 C6 H6 120.1 . . ?
C4 C6 H6 120.1 . . ?
O2 C8 N1 123.74(14) . . ?
O2 C8 C18 120.30(14) . . ?
N1 C8 C18 115.94(13) . . ?
C4 C10 C12 120.71(15) . . ?
C4 C10 C16 118.53(15) . . ?
C16 C10 C12 120.76(15) . . ?
C11 C12 C10 179.2(2) . . ?
C1 C14 H14 119.4 . . ?
C16 C14 C1 121.21(16) . . ?
C16 C14 H14 119.4 . . ?
C10 C16 H16 119.9 . . ?
C14 C16 C10 120.12(16) . . ?
C14 C16 H16 119.9 . . ?
C8 C18 C9 119.98(13) . . ?
C8 C18 C3 113.70(12) . . ?
C8 C18 C7 115.16(12) . . ?
C9 C18 C3 103.28(12) . . ?
C9 C18 C7 100.09(13) . . ?
C7 C18 C3 102.22(13) . . ?
O1 C9 C18 127.73(14) . . ?
O1 C9 C5 125.83(15) . . ?
C5 C9 C18 106.43(13) . . ?
C9 C5 H5A 111.3 . . ?
C9 C5 H5B 111.3 . . ?
C9 C5 C13 102.17(13) . . ?
H5A C5 H5B 109.2 . . ?
C13 C5 H5A 111.3 . . ?
C13 C5 H5B 111.3 . . ?
C12 C11 H11 180.0 . . ?
C18 C3 H3A 111.0 . . ?
C18 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C2 C3 C18 103.98(13) . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C5 C13 H13 114.3 . . ?
C5 C13 C7 102.81(13) . . ?
C7 C13 H13 114.3 . . ?
C2 C13 C5 106.86(15) . . ?
C2 C13 H13 114.3 . . ?
C2 C13 C7 102.94(14) . . ?
C13 C7 C18 93.50(12) . . ?
C15 C7 C18 112.32(14) . . ?
C15 C7 C13 113.83(15) . . ?
C15 C7 C17 108.93(16) . . ?
C17 C7 C18 114.76(15) . . ?
C17 C7 C13 112.95(14) . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C13 C2 C3 102.74(13) . . ?
C13 C2 H2A 111.2 . . ?
C13 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 C9 C5 C13 -178.09(16) . . . . ?
O2 C8 C18 C9 -176.03(15) . . . . ?
O2 C8 C18 C3 -53.2(2) . . . . ?
O2 C8 C18 C7 64.34(19) . . . . ?
N1 C1 C6 C4 179.72(15) . . . . ?
N1 C1 C14 C16 -179.56(16) . . . . ?
N1 C8 C18 C9 5.5(2) . . . . ?
N1 C8 C18 C3 128.38(15) . . . . ?
N1 C8 C18 C7 -114.12(16) . . . . ?
C1 N1 C8 O2 4.5(3) . . . . ?
C1 N1 C8 C18 -177.08(14) . . . . ?
C1 C14 C16 C10 -0.2(3) . . . . ?
C4 C10 C16 C14 0.3(3) . . . . ?
C6 C1 C14 C16 -0.2(3) . . . . ?
C6 C4 C10 C12 179.64(15) . . . . ?
C6 C4 C10 C16 -0.1(2) . . . . ?
C8 N1 C1 C6 0.2(2) . . . . ?
C8 N1 C1 C14 179.55(16) . . . . ?
C8 C18 C9 O1 16.4(2) . . . . ?
C8 C18 C9 C5 -162.67(14) . . . . ?
C8 C18 C3 C2 156.16(13) . . . . ?
C8 C18 C7 C13 -176.11(14) . . . . ?
C8 C18 C7 C15 66.33(18) . . . . ?
C8 C18 C7 C17 -58.82(19) . . . . ?
C10 C4 C6 C1 -0.3(2) . . . . ?
C12 C10 C16 C14 -179.42(16) . . . . ?
C14 C1 C6 C4 0.4(2) . . . . ?
C18 C9 C5 C13 1.05(16) . . . . ?
C18 C3 C2 C13 3.95(17) . . . . ?
C9 C18 C3 C2 -72.21(15) . . . . ?
C9 C18 C7 C13 53.78(14) . . . . ?
C9 C18 C7 C15 -63.79(16) . . . . ?
C9 C18 C7 C17 171.07(14) . . . . ?
C9 C5 C13 C7 34.43(17) . . . . ?
C9 C5 C13 C2 -73.56(15) . . . . ?
C5 C13 C7 C18 -54.86(15) . . . . ?
C5 C13 C7 C15 61.45(18) . . . . ?
C5 C13 C7 C17 -173.64(16) . . . . ?
C5 C13 C2 C3 69.61(16) . . . . ?
C3 C18 C9 O1 -111.35(18) . . . . ?
C3 C18 C9 C5 69.53(15) . . . . ?
C3 C18 C7 C13 -52.32(14) . . . . ?
C3 C18 C7 C15 -169.89(14) . . . . ?
C3 C18 C7 C17 64.97(17) . . . . ?
C7 C18 C9 O1 143.40(17) . . . . ?
C7 C18 C9 C5 -35.72(15) . . . . ?
C7 C18 C3 C2 31.40(16) . . . . ?
C7 C13 C2 C3 -38.29(17) . . . . ?
C2 C13 C7 C18 56.09(15) . . . . ?
C2 C13 C7 C15 172.39(15) . . . . ?
C2 C13 C7 C17 -62.70(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ss
_database_code_depnum_ccdc_archive 'CCDC 2209736'
loop_
_audit_author_name
_audit_author_address
'Xiaolin Zhu'
;Shaanxi Normal University
China
;
_audit_update_record             
;
2022-11-09 deposited with the CCDC.	2023-08-03 downloaded from the CCDC.
;
_audit_creation_date             2022-11-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H20 N2 O3 S'
_chemical_formula_sum            'C17 H20 N2 O3 S'
_chemical_formula_weight         332.41
_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 0.0181 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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.1344(6)
_cell_length_b                   10.1798(9)
_cell_length_c                   11.5186(10)
_cell_angle_alpha                105.967(2)
_cell_angle_beta                 92.665(2)
_cell_angle_gamma                91.935(2)
_cell_volume                     802.47(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    250.00
_cell_measurement_theta_max      68.210
_cell_measurement_theta_min      7.519
_shelx_estimated_absorpt_T_max   0.830
_shelx_estimated_absorpt_T_min   0.511
_exptl_absorpt_coefficient_mu    1.936
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0889 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.8709.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21268
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.342
_diffrn_reflns_theta_min         7.201
_diffrn_ambient_temperature      250.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.890
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                5464
_reflns_number_total             5496
_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       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 2543 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.088(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5496
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.027
_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)+(0.0482P)²+0.2018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0790
_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 Ternary CH refined with riding coordinates:
 C28(H28), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B), C26(H26A,H26B), C9(H9A,H9B), C27(H27A,H27B),
 C7(H7A,H7B), C31(H31A,H31B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4A), N4(H4), C24(H24), C30(H30), C32(H32), C34(H34), C19(H19),
 C5(H5), C15(H15)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C1(H1A,H1B,H1C)
;
_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 0.42495(7) 0.37827(6) 0.29095(5) 0.02058(16) Uani 1 1 d . . . . .
S2 S 1.59023(7) 0.61154(6) 0.71766(5) 0.02156(17) Uani 1 1 d . . . . .
O1 O 0.3381(3) 0.3575(2) 0.3945(2) 0.0271(5) Uani 1 1 d . . . . .
N1 N 0.8627(4) 0.2971(3) 0.8907(3) 0.0303(6) Uani 1 1 d . . . . .
O4 O 0.3131(3) 0.4127(2) 0.1980(2) 0.0286(5) Uani 1 1 d . . . . .
O6 O 1.6986(3) 0.5840(2) 0.8148(2) 0.0299(5) Uani 1 1 d . . . . .
N3 N 1.4457(4) 0.4785(3) 0.6573(2) 0.0248(5) Uani 1 1 d . . . . .
H3 H 1.458578 0.431660 0.582838 0.030 Uiso 1 1 calc R U . . .
C4 C 1.1835(5) 0.3839(3) 0.8973(3) 0.0300(7) Uani 1 1 d . . . . .
H4A H 1.201556 0.378634 0.977258 0.036 Uiso 1 1 calc R U . . .
N4 N 0.5851(4) 0.5016(3) 0.3468(2) 0.0246(6) Uani 1 1 d . . . . .
H4 H 0.585713 0.541861 0.423931 0.030 Uiso 1 1 calc R U . . .
C6 C 1.3006(5) 0.4371(3) 0.7219(3) 0.0237(6) Uani 1 1 d . . . . .
O3 O 1.6847(3) 0.6351(2) 0.6168(2) 0.0287(5) Uani 1 1 d . . . . .
C8 C 1.0098(5) 0.3481(3) 0.8357(3) 0.0271(7) Uani 1 1 d . . . . .
C10 C 0.6664(5) -0.0654(3) 0.3396(3) 0.0341(7) Uani 1 1 d . . . . .
H10A H 0.640593 -0.155574 0.281852 0.041 Uiso 1 1 calc R U . . .
H10B H 0.660629 -0.073854 0.422075 0.041 Uiso 1 1 calc R U . . .
C12 C 1.2712(5) 0.7802(3) 0.5954(3) 0.0279(7) Uani 1 1 d . . . . .
C14 C 0.6505(4) 0.1505(3) 0.2862(3) 0.0208(6) Uani 1 1 d . . . . .
C16 C 0.8099(4) 0.0637(3) 0.2175(3) 0.0220(6) Uani 1 1 d . . . . .
C18 C 0.5311(5) 0.0375(3) 0.3168(3) 0.0273(7) Uani 1 1 d . . . . .
C20 C 1.1627(6) 0.8936(3) 0.5649(3) 0.0404(9) Uani 1 1 d . . . . .
H20A H 1.027293 0.870751 0.555157 0.049 Uiso 1 1 calc R U . . .
H20B H 1.204822 0.912323 0.490945 0.049 Uiso 1 1 calc R U . . .
O2 O 1.2681(3) 0.6623(2) 0.53592(18) 0.0345(5) Uani 1 1 d . . . . .
C22 C 0.7360(5) -0.0395(3) 0.0982(3) 0.0271(7) Uani 1 1 d . . . . .
H22A H 0.623206 -0.087619 0.111990 0.041 Uiso 1 1 calc R U . . .
H22B H 0.831036 -0.104626 0.069261 0.041 Uiso 1 1 calc R U . . .
H22C H 0.707152 0.008878 0.038350 0.041 Uiso 1 1 calc R U . . .
C24 C 0.9001(5) 0.5920(3) 0.3400(3) 0.0244(6) Uani 1 1 d . . . . .
H24 H 0.924254 0.586718 0.419465 0.029 Uiso 1 1 calc R U . . .
C26 C 1.4516(4) 0.7519(3) 0.7884(3) 0.0218(6) Uani 1 1 d . . . . .
H26A H 1.342787 0.714011 0.819465 0.026 Uiso 1 1 calc R U . . .
H26B H 1.526599 0.809167 0.858653 0.026 Uiso 1 1 calc R U . . .
C28 C 1.2120(5) 1.0155(3) 0.6765(3) 0.0366(8) Uani 1 1 d . . . . .
H28 H 1.121010 1.088727 0.689193 0.044 Uiso 1 1 calc R U . . .
O5 O 0.3621(3) 0.0311(2) 0.3200(2) 0.0394(5) Uani 1 1 d . . . . .
C30 C 1.0378(4) 0.6420(3) 0.2825(3) 0.0252(7) Uani 1 1 d . . . . .
H30 H 1.155875 0.671962 0.322413 0.030 Uiso 1 1 calc R U . . .
C32 C 1.3308(5) 0.4276(3) 0.8403(3) 0.0270(7) Uani 1 1 d . . . . .
H32 H 1.449834 0.450662 0.880794 0.032 Uiso 1 1 calc R U . . .
C34 C 0.9786(5) 0.3570(3) 0.7189(3) 0.0278(7) Uani 1 1 d . . . . .
H34 H 0.860113 0.331834 0.678051 0.033 Uiso 1 1 calc R U . . .
C17 C 1.0014(5) 0.6480(3) 0.1645(3) 0.0253(7) Uani 1 1 d . . . . .
C9 C 0.5442(4) 0.2314(3) 0.2142(3) 0.0218(6) Uani 1 1 d . . . . .
H9A H 0.451127 0.168123 0.159640 0.026 Uiso 1 1 calc R U . . .
H9B H 0.633780 0.260763 0.163190 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6883(5) 0.5553(3) 0.1635(3) 0.0286(7) Uani 1 1 d . . . . .
H19 H 0.569924 0.526639 0.123421 0.034 Uiso 1 1 calc R U . . .
C5 C 1.1244(5) 0.4034(3) 0.6628(3) 0.0260(7) Uani 1 1 d . . . . .
H5 H 1.103732 0.412180 0.584128 0.031 Uiso 1 1 calc R U . . .
C21 C 1.2988(5) 1.0395(3) 0.9030(3) 0.0294(7) Uani 1 1 d . . . . .
H21A H 1.415919 1.085908 0.893952 0.044 Uiso 1 1 calc R U . . .
H21B H 1.319484 0.986254 0.960067 0.044 Uiso 1 1 calc R U . . .
H21C H 1.206383 1.106633 0.932610 0.044 Uiso 1 1 calc R U . . .
C11 C 0.7229(4) 0.5485(3) 0.2807(3) 0.0215(6) Uani 1 1 d . . . . .
C23 C 1.0469(5) 0.8690(4) 0.7983(4) 0.0400(9) Uani 1 1 d . . . . .
H23A H 0.949337 0.933765 0.821029 0.060 Uiso 1 1 calc R U . . .
H23B H 1.069968 0.824551 0.861652 0.060 Uiso 1 1 calc R U . . .
H23C H 1.006994 0.800769 0.723440 0.060 Uiso 1 1 calc R U . . .
C35 C 1.3787(4) 0.8448(3) 0.7163(3) 0.0213(6) Uani 1 1 d . . . . .
C25 C 0.8573(5) -0.0022(3) 0.3207(3) 0.0292(7) Uani 1 1 d . . . . .
H25 H 0.958872 -0.067565 0.304136 0.035 Uiso 1 1 calc R U . . .
C2 C 0.7404(6) 0.2531(4) 0.9325(4) 0.0432(9) Uani 1 1 d . . . . .
N13 N 1.1437(4) 0.7005(3) 0.1072(3) 0.0331(7) Uani 1 1 d . . . . .
C3 C 1.2656(7) 0.7447(5) 0.0632(4) 0.0480(10) Uani 1 1 d . . . . .
C27 C 0.7587(5) 0.2279(3) 0.4079(3) 0.0291(7) Uani 1 1 d . . . . .
H27A H 0.823497 0.311675 0.401226 0.035 Uiso 1 1 calc R U . . .
H27B H 0.672903 0.251675 0.473744 0.035 Uiso 1 1 calc R U . . .
C7 C 1.5283(5) 0.9445(3) 0.6881(3) 0.0306(7) Uani 1 1 d . . . . .
H7A H 1.593494 0.899639 0.615787 0.037 Uiso 1 1 calc R U . . .
H7B H 1.621192 0.977784 0.756330 0.037 Uiso 1 1 calc R U . . .
C29 C 1.2270(5) 0.9445(3) 0.7804(3) 0.0266(7) Uani 1 1 d . . . . .
C15 C 0.8293(5) 0.6048(3) 0.1050(3) 0.0286(7) Uani 1 1 d . . . . .
H15 H 0.807058 0.608618 0.024961 0.034 Uiso 1 1 calc R U . . .
C31 C 0.9017(5) 0.1242(4) 0.4298(3) 0.0360(8) Uani 1 1 d . . . . .
H31A H 1.031309 0.159799 0.430793 0.043 Uiso 1 1 calc R U . . .
H31B H 0.882467 0.102344 0.506287 0.043 Uiso 1 1 calc R U . . .
C1 C 0.9735(4) 0.1480(4) 0.1893(4) 0.0353(8) Uani 1 1 d . . . . .
H1A H 0.933448 0.188059 0.125542 0.053 Uiso 1 1 calc R U . . .
H1B H 1.076760 0.089448 0.163211 0.053 Uiso 1 1 calc R U . . .
H1C H 1.014200 0.220223 0.261386 0.053 Uiso 1 1 calc R U . . .
C33 C 1.4135(6) 1.0638(4) 0.6670(3) 0.0417(9) Uani 1 1 d . . . . .
H33A H 1.447846 1.149745 0.728968 0.050 Uiso 1 1 calc R U . . .
H33B H 1.432376 1.076467 0.586947 0.050 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 O1 1.432(2) . ?
S1 O4 1.432(2) . ?
S1 N4 1.639(3) . ?
S1 C9 1.780(3) . ?
S2 O6 1.427(2) . ?
S2 N3 1.643(3) . ?
S2 O3 1.441(2) . ?
S2 C26 1.792(3) . ?
N1 C8 1.407(4) . ?
N1 C2 1.151(5) . ?
N3 H3 0.8700 . ?
N3 C6 1.420(4) . ?
C4 H4A 0.9400 . ?
C4 C8 1.385(5) . ?
C4 C32 1.388(5) . ?
N4 H4 0.8700 . ?
N4 C11 1.418(4) . ?
C6 C32 1.401(4) . ?
C6 C5 1.387(5) . ?
C8 C34 1.381(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 C18 1.515(5) . ?
C10 C25 1.536(5) . ?
C12 C20 1.522(4) . ?
C12 O2 1.207(4) . ?
C12 C35 1.524(4) . ?
C14 C16 1.571(4) . ?
C14 C18 1.536(4) . ?
C14 C9 1.517(4) . ?
C14 C27 1.559(4) . ?
C16 C22 1.539(4) . ?
C16 C25 1.547(4) . ?
C16 C1 1.524(4) . ?
C18 O5 1.208(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 C28 1.539(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C24 H24 0.9400 . ?
C24 C30 1.369(4) . ?
C24 C11 1.406(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 C35 1.510(4) . ?
C28 H28 0.9900 . ?
C28 C29 1.560(4) . ?
C28 C33 1.522(6) . ?
C30 H30 0.9400 . ?
C30 C17 1.390(4) . ?
C32 H32 0.9400 . ?
C34 H34 0.9400 . ?
C34 C5 1.386(5) . ?
C17 N13 1.404(4) . ?
C17 C15 1.375(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C19 H19 0.9400 . ?
C19 C11 1.383(5) . ?
C19 C15 1.391(5) . ?
C5 H5 0.9400 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C21 C29 1.529(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C23 C29 1.526(5) . ?
C35 C7 1.554(4) . ?
C35 C29 1.575(4) . ?
C25 H25 0.9900 . ?
C25 C31 1.543(5) . ?
N13 C3 1.165(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 C31 1.554(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 C33 1.554(5) . ?
C15 H15 0.9400 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C33 H33A 0.9800 . ?
C33 H33B 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
O1 S1 O4 119.76(13) . . ?
O1 S1 N4 104.60(13) . . ?
O1 S1 C9 111.28(14) . . ?
O4 S1 N4 108.70(13) . . ?
O4 S1 C9 104.82(14) . . ?
N4 S1 C9 107.13(14) . . ?
O6 S2 N3 108.08(13) . . ?
O6 S2 O3 119.21(14) . . ?
O6 S2 C26 104.84(14) . . ?
N3 S2 C26 107.64(14) . . ?
O3 S2 N3 104.52(14) . . ?
O3 S2 C26 112.09(14) . . ?
C2 N1 C8 178.0(4) . . ?
S2 N3 H3 118.7 . . ?
C6 N3 S2 122.6(2) . . ?
C6 N3 H3 118.7 . . ?
C8 C4 H4A 120.2 . . ?
C8 C4 C32 119.5(3) . . ?
C32 C4 H4A 120.2 . . ?
S1 N4 H4 117.1 . . ?
C11 N4 S1 125.9(2) . . ?
C11 N4 H4 117.1 . . ?
C32 C6 N3 122.5(3) . . ?
C5 C6 N3 117.6(3) . . ?
C5 C6 C32 120.0(3) . . ?
C4 C8 N1 119.8(3) . . ?
C34 C8 N1 118.7(3) . . ?
C34 C8 C4 121.4(3) . . ?
H10A C10 H10B 109.2 . . ?
C18 C10 H10A 111.3 . . ?
C18 C10 H10B 111.3 . . ?
C18 C10 C25 102.3(2) . . ?
C25 C10 H10A 111.3 . . ?
C25 C10 H10B 111.3 . . ?
C20 C12 C35 106.4(3) . . ?
O2 C12 C20 126.1(3) . . ?
O2 C12 C35 127.5(3) . . ?
C18 C14 C16 100.2(2) . . ?
C18 C14 C27 104.7(2) . . ?
C9 C14 C16 114.6(2) . . ?
C9 C14 C18 114.4(3) . . ?
C9 C14 C27 119.4(3) . . ?
C27 C14 C16 101.0(2) . . ?
C22 C16 C14 112.6(2) . . ?
C22 C16 C25 113.9(3) . . ?
C25 C16 C14 93.9(2) . . ?
C1 C16 C14 114.5(3) . . ?
C1 C16 C22 107.8(3) . . ?
C1 C16 C25 113.8(3) . . ?
C10 C18 C14 106.5(3) . . ?
O5 C18 C10 126.8(3) . . ?
O5 C18 C14 126.6(3) . . ?
C12 C20 H20A 111.4 . . ?
C12 C20 H20B 111.4 . . ?
C12 C20 C28 102.1(3) . . ?
H20A C20 H20B 109.2 . . ?
C28 C20 H20A 111.4 . . ?
C28 C20 H20B 111.4 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C30 C24 H24 119.8 . . ?
C30 C24 C11 120.3(3) . . ?
C11 C24 H24 119.8 . . ?
S2 C26 H26A 107.4 . . ?
S2 C26 H26B 107.4 . . ?
H26A C26 H26B 106.9 . . ?
C35 C26 S2 119.7(2) . . ?
C35 C26 H26A 107.4 . . ?
C35 C26 H26B 107.4 . . ?
C20 C28 H28 114.2 . . ?
C20 C28 C29 102.1(3) . . ?
C29 C28 H28 114.2 . . ?
C33 C28 C20 107.1(3) . . ?
C33 C28 H28 114.2 . . ?
C33 C28 C29 103.7(3) . . ?
C24 C30 H30 120.3 . . ?
C24 C30 C17 119.4(3) . . ?
C17 C30 H30 120.3 . . ?
C4 C32 C6 119.5(3) . . ?
C4 C32 H32 120.3 . . ?
C6 C32 H32 120.3 . . ?
C8 C34 H34 120.5 . . ?
C8 C34 C5 119.1(3) . . ?
C5 C34 H34 120.5 . . ?
C30 C17 N13 118.6(3) . . ?
C15 C17 C30 121.0(3) . . ?
C15 C17 N13 120.4(3) . . ?
S1 C9 H9A 107.4 . . ?
S1 C9 H9B 107.4 . . ?
C14 C9 S1 119.8(2) . . ?
C14 C9 H9A 107.4 . . ?
C14 C9 H9B 107.4 . . ?
H9A C9 H9B 106.9 . . ?
C11 C19 H19 120.2 . . ?
C11 C19 C15 119.7(3) . . ?
C15 C19 H19 120.2 . . ?
C6 C5 H5 119.8 . . ?
C34 C5 C6 120.5(3) . . ?
C34 C5 H5 119.8 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C29 C21 H21A 109.5 . . ?
C29 C21 H21B 109.5 . . ?
C29 C21 H21C 109.5 . . ?
C24 C11 N4 117.4(3) . . ?
C19 C11 N4 122.9(3) . . ?
C19 C11 C24 119.7(3) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C23 H23A 109.5 . . ?
C29 C23 H23B 109.5 . . ?
C29 C23 H23C 109.5 . . ?
C12 C35 C7 104.6(3) . . ?
C12 C35 C29 99.2(2) . . ?
C26 C35 C12 118.4(3) . . ?
C26 C35 C7 115.4(3) . . ?
C26 C35 C29 114.3(2) . . ?
C7 C35 C29 102.6(2) . . ?
C10 C25 C16 102.9(3) . . ?
C10 C25 H25 114.4 . . ?
C10 C25 C31 107.1(3) . . ?
C16 C25 H25 114.4 . . ?
C31 C25 C16 102.2(3) . . ?
C31 C25 H25 114.4 . . ?
C3 N13 C17 177.7(4) . . ?
C14 C27 H27A 110.9 . . ?
C14 C27 H27B 110.9 . . ?
H27A C27 H27B 109.0 . . ?
C31 C27 C14 104.0(2) . . ?
C31 C27 H27A 110.9 . . ?
C31 C27 H27B 110.9 . . ?
C35 C7 H7A 110.9 . . ?
C35 C7 H7B 110.9 . . ?
C35 C7 C33 104.3(3) . . ?
H7A C7 H7B 108.9 . . ?
C33 C7 H7A 110.9 . . ?
C33 C7 H7B 110.9 . . ?
C28 C29 C35 93.0(2) . . ?
C21 C29 C28 114.2(3) . . ?
C21 C29 C35 113.3(3) . . ?
C23 C29 C28 114.8(3) . . ?
C23 C29 C21 108.3(3) . . ?
C23 C29 C35 112.8(3) . . ?
C17 C15 C19 119.9(3) . . ?
C17 C15 H15 120.1 . . ?
C19 C15 H15 120.1 . . ?
C25 C31 C27 102.9(3) . . ?
C25 C31 H31A 111.2 . . ?
C25 C31 H31B 111.2 . . ?
C27 C31 H31A 111.2 . . ?
C27 C31 H31B 111.2 . . ?
H31A C31 H31B 109.1 . . ?
C16 C1 H1A 109.5 . . ?
C16 C1 H1B 109.5 . . ?
C16 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C28 C33 C7 102.6(3) . . ?
C28 C33 H33A 111.2 . . ?
C28 C33 H33B 111.2 . . ?
C7 C33 H33A 111.2 . . ?
C7 C33 H33B 111.2 . . ?
H33A C33 H33B 109.2 . . ?

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 N4 C11 C24 -145.2(3) . . . . ?
S1 N4 C11 C19 36.2(4) . . . . ?
S2 N3 C6 C32 -45.9(4) . . . . ?
S2 N3 C6 C5 135.0(3) . . . . ?
S2 C26 C35 C12 52.0(4) . . . . ?
S2 C26 C35 C7 -73.1(3) . . . . ?
S2 C26 C35 C29 168.3(2) . . . . ?
O1 S1 N4 C11 172.5(2) . . . . ?
O1 S1 C9 C14 -38.5(3) . . . . ?
N1 C8 C34 C5 -178.2(3) . . . . ?
O4 S1 N4 C11 -58.5(3) . . . . ?
O4 S1 C9 C14 -169.3(2) . . . . ?
O6 S2 N3 C6 64.2(3) . . . . ?
O6 S2 C26 C35 155.9(2) . . . . ?
N3 S2 C26 C35 -89.2(3) . . . . ?
N3 C6 C32 C4 -178.8(3) . . . . ?
N3 C6 C5 C34 177.4(3) . . . . ?
C4 C8 C34 C5 -0.4(5) . . . . ?
N4 S1 C9 C14 75.3(3) . . . . ?
O3 S2 N3 C6 -167.8(2) . . . . ?
O3 S2 C26 C35 25.2(3) . . . . ?
C8 C4 C32 C6 1.1(5) . . . . ?
C8 C34 C5 C6 1.7(5) . . . . ?
C10 C25 C31 C27 -70.9(3) . . . . ?
C12 C20 C28 C29 -34.4(4) . . . . ?
C12 C20 C28 C33 74.2(3) . . . . ?
C12 C35 C7 C33 71.9(3) . . . . ?
C12 C35 C29 C28 -55.7(3) . . . . ?
C12 C35 C29 C21 -173.8(3) . . . . ?
C12 C35 C29 C23 62.8(3) . . . . ?
C14 C16 C25 C10 54.8(3) . . . . ?
C14 C16 C25 C31 -56.2(3) . . . . ?
C14 C27 C31 C25 -1.4(3) . . . . ?
C16 C14 C18 C10 34.0(3) . . . . ?
C16 C14 C18 O5 -144.9(3) . . . . ?
C16 C14 C9 S1 -157.0(2) . . . . ?
C16 C14 C27 C31 -33.7(3) . . . . ?
C16 C25 C31 C27 36.8(3) . . . . ?
C18 C10 C25 C16 -35.4(3) . . . . ?
C18 C10 C25 C31 71.9(3) . . . . ?
C18 C14 C16 C22 65.0(3) . . . . ?
C18 C14 C16 C25 -52.9(3) . . . . ?
C18 C14 C16 C1 -171.3(3) . . . . ?
C18 C14 C9 S1 88.1(3) . . . . ?
C18 C14 C27 C31 70.0(3) . . . . ?
C20 C12 C35 C26 161.7(3) . . . . ?
C20 C12 C35 C7 -68.1(3) . . . . ?
C20 C12 C35 C29 37.6(3) . . . . ?
C20 C28 C29 C21 173.0(3) . . . . ?
C20 C28 C29 C23 -61.0(4) . . . . ?
C20 C28 C29 C35 55.8(3) . . . . ?
C20 C28 C33 C7 -69.4(3) . . . . ?
O2 C12 C20 C28 176.2(3) . . . . ?
O2 C12 C35 C26 -16.9(5) . . . . ?
O2 C12 C35 C7 113.4(4) . . . . ?
O2 C12 C35 C29 -141.0(4) . . . . ?
C22 C16 C25 C10 -62.1(3) . . . . ?
C22 C16 C25 C31 -173.1(3) . . . . ?
C24 C30 C17 N13 179.5(3) . . . . ?
C24 C30 C17 C15 0.1(5) . . . . ?
C26 S2 N3 C6 -48.5(3) . . . . ?
C26 C35 C7 C33 -156.1(3) . . . . ?
C26 C35 C29 C28 177.2(3) . . . . ?
C26 C35 C29 C21 59.2(4) . . . . ?
C26 C35 C29 C23 -64.2(4) . . . . ?
C30 C24 C11 N4 -178.2(3) . . . . ?
C30 C24 C11 C19 0.5(5) . . . . ?
C30 C17 C15 C19 0.6(5) . . . . ?
C32 C4 C8 N1 176.7(3) . . . . ?
C32 C4 C8 C34 -1.0(5) . . . . ?
C32 C6 C5 C34 -1.7(5) . . . . ?
C9 S1 N4 C11 54.3(3) . . . . ?
C9 C14 C16 C22 -57.9(3) . . . . ?
C9 C14 C16 C25 -175.8(2) . . . . ?
C9 C14 C16 C1 65.8(3) . . . . ?
C9 C14 C18 C10 157.1(3) . . . . ?
C9 C14 C18 O5 -21.8(4) . . . . ?
C9 C14 C27 C31 -160.4(3) . . . . ?
C5 C6 C32 C4 0.3(5) . . . . ?
C11 C24 C30 C17 -0.7(5) . . . . ?
C11 C19 C15 C17 -0.8(5) . . . . ?
C35 C12 C20 C28 -2.4(4) . . . . ?
C35 C7 C33 C28 -3.7(4) . . . . ?
C25 C10 C18 C14 0.3(3) . . . . ?
C25 C10 C18 O5 179.2(3) . . . . ?
N13 C17 C15 C19 -178.8(3) . . . . ?
C27 C14 C16 C22 172.4(3) . . . . ?
C27 C14 C16 C25 54.4(3) . . . . ?
C27 C14 C16 C1 -63.9(3) . . . . ?
C27 C14 C18 C10 -70.4(3) . . . . ?
C27 C14 C18 O5 110.7(4) . . . . ?
C27 C14 C9 S1 -37.0(4) . . . . ?
C7 C35 C29 C28 51.6(3) . . . . ?
C7 C35 C29 C21 -66.4(3) . . . . ?
C7 C35 C29 C23 170.1(3) . . . . ?
C29 C28 C33 C7 38.1(3) . . . . ?
C29 C35 C7 C33 -31.3(3) . . . . ?
C15 C19 C11 N4 178.8(3) . . . . ?
C15 C19 C11 C24 0.2(5) . . . . ?
C1 C16 C25 C10 173.8(3) . . . . ?
C1 C16 C25 C31 62.8(3) . . . . ?
C33 C28 C29 C21 61.8(4) . . . . ?
C33 C28 C29 C23 -172.2(3) . . . . ?
C33 C28 C29 C35 -55.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_s_pl
_database_code_depnum_ccdc_archive 'CCDC 2209735'
loop_
_audit_author_name
_audit_author_address
'Xiaolin Zhu'
;Shaanxi Normal University
China
;
_audit_update_record             
;
2022-09-27 deposited with the CCDC.	2023-08-03 downloaded from the CCDC.
;
_audit_creation_date             2022-05-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 N O3 S'
_chemical_formula_sum            'C18 H21 N O3 S'
_chemical_formula_weight         331.42
_chemical_absolute_configuration rmad
_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 0.0181 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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.7823(6)
_cell_length_b                   10.1497(6)
_cell_length_c                   18.5221(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1651.02(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9823
_cell_measurement_temperature    153.15
_cell_measurement_theta_max      68.138
_cell_measurement_theta_min      2.385
_shelx_estimated_absorpt_T_max   0.605
_shelx_estimated_absorpt_T_min   0.456
_exptl_absorpt_coefficient_mu    1.862
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1305 before and 0.0876 after correction.
The Ratio of minimum to maximum transmission is 0.7683.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23753
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.259
_diffrn_reflns_theta_min         6.666
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2960
_reflns_number_total             2975
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.10(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2975
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.106
_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)+(0.0457P)²+0.4406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0820
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.90(2)
 0.10(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:
 C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C18(H18A,H18B), C3(H3A,H3B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C8(H8), C9(H9), C11(H11)
3.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C17(H17A,H17B,H17C)
3.e :
 C15(H15)
;
_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 0.08342(6) 0.76260(5) 0.19005(3) 0.02439(16) Uani 1 1 d . . . . .
O1 O 0.0253(2) 0.68472(19) 0.13198(9) 0.0313(4) Uani 1 1 d . . . . .
O3 O 0.0270(2) 0.89381(18) 0.20050(10) 0.0339(4) Uani 1 1 d . . . . .
O2 O 0.2785(2) 0.48787(17) 0.20673(10) 0.0330(4) Uani 1 1 d . . . . .
N1 N 0.0481(2) 0.6784(2) 0.26368(11) 0.0254(4) Uani 1 1 d . . . . .
H1 H 0.000071 0.602501 0.260659 0.030 Uiso 1 1 calc R U . . .
C1 C 0.0945(3) 0.7270(2) 0.33290(12) 0.0240(5) Uani 1 1 d . . . . .
C4 C 0.3732(3) 0.6774(2) 0.13911(12) 0.0228(5) Uani 1 1 d . . . . .
C6 C 0.2353(3) 0.6915(3) 0.44217(15) 0.0333(6) Uani 1 1 d . . . . .
H6 H 0.302861 0.638897 0.470011 0.040 Uiso 1 1 calc R U . . .
C8 C 0.1951(3) 0.6514(2) 0.37382(14) 0.0303(5) Uani 1 1 d . . . . .
H8 H 0.235950 0.572177 0.354506 0.036 Uiso 1 1 calc R U . . .
C10 C 0.3677(3) 0.5351(2) 0.16435(13) 0.0255(5) Uani 1 1 d . . . . .
C12 C 0.1778(3) 0.8089(2) 0.47124(14) 0.0279(5) Uani 1 1 d . . . . .
C14 C 0.5004(3) 0.4649(3) 0.12764(16) 0.0365(6) Uani 1 1 d . . . . .
H14A H 0.464097 0.396690 0.093547 0.044 Uiso 1 1 calc R U . . .
H14B H 0.569319 0.423866 0.163457 0.044 Uiso 1 1 calc R U . . .
C16 C 0.5792(3) 0.5793(2) 0.08763(14) 0.0313(5) Uani 1 1 d . . . . .
H16 H 0.688841 0.563151 0.076139 0.038 Uiso 1 1 calc R U . . .
C18 C 0.2873(3) 0.7789(2) 0.18282(13) 0.0268(5) Uani 1 1 d . . . . .
H18A H 0.309211 0.866565 0.161819 0.032 Uiso 1 1 calc R U . . .
H18B H 0.329743 0.778491 0.232328 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0785(3) 0.8841(2) 0.42895(13) 0.0281(5) Uani 1 1 d . . . . .
H9 H 0.039484 0.964554 0.447538 0.034 Uiso 1 1 calc R U . . .
C5 C 0.2221(3) 0.8510(3) 0.54237(14) 0.0345(6) Uani 1 1 d . . . . .
C11 C 0.0363(3) 0.8435(2) 0.36059(13) 0.0268(5) Uani 1 1 d . . . . .
H11 H -0.032215 0.895141 0.332742 0.032 Uiso 1 1 calc R U . . .
C3 C 0.3358(3) 0.6716(3) 0.05695(14) 0.0326(6) Uani 1 1 d . . . . .
H3A H 0.245446 0.615658 0.047890 0.039 Uiso 1 1 calc R U . . .
H3B H 0.316238 0.760880 0.037559 0.039 Uiso 1 1 calc R U . . .
C13 C 0.5510(3) 0.6979(3) 0.13890(14) 0.0283(5) Uani 1 1 d . . . . .
C7 C 0.4807(3) 0.6104(3) 0.02208(14) 0.0377(6) Uani 1 1 d . . . . .
H7A H 0.455763 0.529553 -0.005360 0.045 Uiso 1 1 calc R U . . .
H7B H 0.531751 0.674014 -0.010437 0.045 Uiso 1 1 calc R U . . .
C15 C 0.2622(4) 0.8828(3) 0.60077(16) 0.0447(7) Uani 1 1 d . . . . .
H15 H 0.294351 0.908332 0.647688 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6225(3) 0.6797(4) 0.21397(16) 0.0431(7) Uani 1 1 d . . . . .
H2A H 0.604748 0.758944 0.243010 0.065 Uiso 1 1 calc R U . . .
H2B H 0.732247 0.665050 0.208904 0.065 Uiso 1 1 calc R U . . .
H2C H 0.575992 0.603529 0.237879 0.065 Uiso 1 1 calc R U . . .
C17 C 0.6012(3) 0.8295(3) 0.10816(17) 0.0417(7) Uani 1 1 d . . . . .
H17A H 0.551370 0.843943 0.061479 0.063 Uiso 1 1 calc R U . . .
H17B H 0.711898 0.829310 0.101572 0.063 Uiso 1 1 calc R U . . .
H17C H 0.572667 0.900160 0.141568 0.063 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 O1 1.4290(19) . ?
S1 O3 1.4339(18) . ?
S1 N1 1.639(2) . ?
S1 C18 1.803(2) . ?
O2 C10 1.208(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.433(3) . ?
C1 C8 1.394(3) . ?
C1 C11 1.387(3) . ?
C4 C10 1.519(3) . ?
C4 C18 1.512(3) . ?
C4 C3 1.558(3) . ?
C4 C13 1.575(3) . ?
C6 H6 0.9500 . ?
C6 C8 1.376(4) . ?
C6 C12 1.402(4) . ?
C8 H8 0.9500 . ?
C10 C14 1.526(4) . ?
C12 C9 1.399(3) . ?
C12 C5 1.439(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C16 1.541(4) . ?
C16 H16 1.0000 . ?
C16 C13 1.552(3) . ?
C16 C7 1.524(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C11 1.382(4) . ?
C5 C15 1.182(4) . ?
C11 H11 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C7 1.556(4) . ?
C13 C2 1.537(4) . ?
C13 C17 1.518(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C15 H15 0.9500 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
O1 S1 O3 119.48(12) . . ?
O1 S1 N1 105.67(10) . . ?
O1 S1 C18 110.45(11) . . ?
O3 S1 N1 107.85(10) . . ?
O3 S1 C18 105.53(11) . . ?
N1 S1 C18 107.31(11) . . ?
S1 N1 H1 119.6 . . ?
C1 N1 S1 120.75(15) . . ?
C1 N1 H1 119.6 . . ?
C8 C1 N1 118.5(2) . . ?
C11 C1 N1 121.3(2) . . ?
C11 C1 C8 120.1(2) . . ?
C10 C4 C3 104.95(19) . . ?
C10 C4 C13 99.09(18) . . ?
C18 C4 C10 117.9(2) . . ?
C18 C4 C3 116.3(2) . . ?
C18 C4 C13 113.97(19) . . ?
C3 C4 C13 102.22(18) . . ?
C8 C6 H6 119.6 . . ?
C8 C6 C12 120.8(2) . . ?
C12 C6 H6 119.6 . . ?
C1 C8 H8 120.0 . . ?
C6 C8 C1 120.0(2) . . ?
C6 C8 H8 120.0 . . ?
O2 C10 C4 126.7(2) . . ?
O2 C10 C14 126.8(2) . . ?
C4 C10 C14 106.4(2) . . ?
C6 C12 C5 120.5(2) . . ?
C9 C12 C6 118.3(2) . . ?
C9 C12 C5 121.2(2) . . ?
C10 C14 H14A 111.4 . . ?
C10 C14 H14B 111.4 . . ?
C10 C14 C16 101.9(2) . . ?
H14A C14 H14B 109.3 . . ?
C16 C14 H14A 111.4 . . ?
C16 C14 H14B 111.4 . . ?
C14 C16 H16 114.3 . . ?
C14 C16 C13 102.6(2) . . ?
C13 C16 H16 114.3 . . ?
C7 C16 C14 106.5(2) . . ?
C7 C16 H16 114.3 . . ?
C7 C16 C13 103.7(2) . . ?
S1 C18 H18A 107.8 . . ?
S1 C18 H18B 107.8 . . ?
C4 C18 S1 118.23(16) . . ?
C4 C18 H18A 107.8 . . ?
C4 C18 H18B 107.8 . . ?
H18A C18 H18B 107.1 . . ?
C12 C9 H9 119.4 . . ?
C11 C9 C12 121.1(2) . . ?
C11 C9 H9 119.4 . . ?
C15 C5 C12 177.9(3) . . ?
C1 C11 H11 120.2 . . ?
C9 C11 C1 119.6(2) . . ?
C9 C11 H11 120.2 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C7 C3 C4 104.4(2) . . ?
C7 C3 H3A 110.9 . . ?
C7 C3 H3B 110.9 . . ?
C16 C13 C4 93.28(18) . . ?
C2 C13 C4 112.8(2) . . ?
C2 C13 C16 113.3(2) . . ?
C17 C13 C4 113.9(2) . . ?
C17 C13 C16 114.0(2) . . ?
C17 C13 C2 109.1(2) . . ?
C16 C7 C3 102.5(2) . . ?
C16 C7 H7A 111.3 . . ?
C16 C7 H7B 111.3 . . ?
C3 C7 H7A 111.3 . . ?
C3 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
C5 C15 H15 180.0 . . ?
C13 C2 H2A 109.5 . . ?
C13 C2 H2B 109.5 . . ?
C13 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 C1 C8 -119.8(2) . . . . ?
S1 N1 C1 C11 63.0(3) . . . . ?
O1 S1 N1 C1 178.72(18) . . . . ?
O1 S1 C18 C4 -21.7(2) . . . . ?
O3 S1 N1 C1 -52.4(2) . . . . ?
O3 S1 C18 C4 -152.18(18) . . . . ?
O2 C10 C14 C16 -174.1(2) . . . . ?
N1 S1 C18 C4 93.0(2) . . . . ?
N1 C1 C8 C6 -176.3(2) . . . . ?
N1 C1 C11 C9 177.1(2) . . . . ?
C4 C10 C14 C16 4.0(3) . . . . ?
C4 C3 C7 C16 3.8(3) . . . . ?
C6 C12 C9 C11 0.8(4) . . . . ?
C8 C1 C11 C9 0.0(3) . . . . ?
C8 C6 C12 C9 0.0(4) . . . . ?
C8 C6 C12 C5 -179.1(3) . . . . ?
C10 C4 C18 S1 -62.2(3) . . . . ?
C10 C4 C3 C7 -72.0(2) . . . . ?
C10 C4 C13 C16 55.9(2) . . . . ?
C10 C4 C13 C2 -61.1(3) . . . . ?
C10 C4 C13 C17 174.0(2) . . . . ?
C10 C14 C16 C13 33.0(3) . . . . ?
C10 C14 C16 C7 -75.6(2) . . . . ?
C12 C6 C8 C1 -0.8(4) . . . . ?
C12 C9 C11 C1 -0.8(4) . . . . ?
C14 C16 C13 C4 -55.1(2) . . . . ?
C14 C16 C13 C2 61.5(3) . . . . ?
C14 C16 C13 C17 -173.1(2) . . . . ?
C14 C16 C7 C3 69.5(3) . . . . ?
C18 S1 N1 C1 60.8(2) . . . . ?
C18 C4 C10 O2 16.2(4) . . . . ?
C18 C4 C10 C14 -161.9(2) . . . . ?
C18 C4 C3 C7 155.8(2) . . . . ?
C18 C4 C13 C16 -178.0(2) . . . . ?
C18 C4 C13 C2 65.0(3) . . . . ?
C18 C4 C13 C17 -59.9(3) . . . . ?
C5 C12 C9 C11 179.9(2) . . . . ?
C11 C1 C8 C6 0.8(4) . . . . ?
C3 C4 C10 O2 -115.1(3) . . . . ?
C3 C4 C10 C14 66.8(2) . . . . ?
C3 C4 C18 S1 63.7(3) . . . . ?
C3 C4 C13 C16 -51.7(2) . . . . ?
C3 C4 C13 C2 -168.6(2) . . . . ?
C3 C4 C13 C17 66.4(3) . . . . ?
C13 C4 C10 O2 139.6(2) . . . . ?
C13 C4 C10 C14 -38.5(2) . . . . ?
C13 C4 C18 S1 -177.73(17) . . . . ?
C13 C4 C3 C7 31.0(3) . . . . ?
C13 C16 C7 C3 -38.3(3) . . . . ?
C7 C16 C13 C4 55.7(2) . . . . ?
C7 C16 C13 C2 172.2(2) . . . . ?
C7 C16 C13 C17 -62.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.90(2)
2 0.10(2)

