# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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. 
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#######################################################################

data_sa4100
_database_code_depnum_ccdc_archive 'CCDC 1063949'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;
_audit_creation_date             2015-05-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H13 N S'
_chemical_formula_sum            'C21 H13 N S'
_chemical_formula_weight         311.38
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.187(3)
_cell_length_b                   10.356(4)
_cell_length_c                   11.075(4)
_cell_angle_alpha                66.214(10)
_cell_angle_beta                 86.273(17)
_cell_angle_gamma                89.284(17)
_cell_volume                     752.6(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2423
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4838
_cell_measurement_theta_min      2.8408
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9625
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.841
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
scan:
	Number of images: 180
	           Slice: -110.0000 - 70.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.0754
	          2theta: -20.0677
scan:
	Number of images: 180
	           Slice: -110.0000 - 70.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.0754
	          2theta: -20.0677
scan:
	Number of images: 172
	           Slice: -110.0000 - 62.0000
	     Image width: 1.0000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.0754
	          2theta: -20.0677
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             3461
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0016
_diffrn_orient_matrix_UB_12      -0.1369
_diffrn_orient_matrix_UB_13      0.0264
_diffrn_orient_matrix_UB_21      -0.0517
_diffrn_orient_matrix_UB_22      -0.0196
_diffrn_orient_matrix_UB_23      -0.0899
_diffrn_orient_matrix_UB_31      0.0981
_diffrn_orient_matrix_UB_32      0.0056
_diffrn_orient_matrix_UB_33      -0.0109
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3156
_reflns_number_total             3458
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.176
_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)+(0.0364P)²+0.3885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1224
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19895(8) 0.38023(6) 1.21088(5) 0.03426(16) Uani 1 1 d . . . . .
N1 N 0.2534(2) 0.64489(19) 1.03835(17) 0.0320(4) Uani 1 1 d . . . . .
C1 C 0.2862(3) 0.7192(2) 0.8995(2) 0.0303(4) Uani 1 1 d . . . . .
C2 C 0.3152(3) 0.8635(2) 0.8322(2) 0.0385(5) Uani 1 1 d . . . . .
H2 H 0.3154 0.9222 0.8774 0.046 Uiso 1 1 calc R . . . .
C3 C 0.3439(3) 0.9180(2) 0.6958(2) 0.0420(5) Uani 1 1 d . . . . .
H3 H 0.3639 1.0145 0.6488 0.050 Uiso 1 1 calc R . . . .
C4 C 0.3432(3) 0.8302(2) 0.6280(2) 0.0374(5) Uani 1 1 d . . . . .
H4 H 0.3615 0.8692 0.5363 0.045 Uiso 1 1 calc R . . . .
C5 C 0.3157(3) 0.6858(2) 0.6948(2) 0.0330(5) Uani 1 1 d . . . . .
H5 H 0.3160 0.6279 0.6489 0.040 Uiso 1 1 calc R . . . .
C6 C 0.2876(3) 0.6289(2) 0.8322(2) 0.0272(4) Uani 1 1 d . . . . .
C7 C 0.2555(3) 0.4869(2) 0.93498(19) 0.0270(4) Uani 1 1 d . . . . .
C8 C 0.2373(3) 0.5127(2) 1.05590(19) 0.0288(4) Uani 1 1 d . . . . .
C9 C 0.2441(3) 0.3579(2) 0.93115(19) 0.0284(4) Uani 1 1 d . . . . .
C10 C 0.2116(3) 0.2294(2) 1.0508(2) 0.0311(4) Uani 1 1 d . . . . .
C11 C 0.1896(3) 0.2292(2) 1.1783(2) 0.0310(4) Uani 1 1 d . . . . .
C12 C 0.1577(3) 0.1027(2) 1.2898(2) 0.0399(5) Uani 1 1 d . . . . .
H12 H 0.1430 0.1038 1.3734 0.048 Uiso 1 1 calc R . . . .
C13 C 0.1482(4) -0.0226(3) 1.2762(2) 0.0472(6) Uani 1 1 d . . . . .
H13 H 0.1269 -0.1062 1.3508 0.057 Uiso 1 1 calc R . . . .
C14 C 0.1699(4) -0.0263(2) 1.1522(2) 0.0475(6) Uani 1 1 d . . . . .
H14 H 0.1643 -0.1118 1.1437 0.057 Uiso 1 1 calc R . . . .
C15 C 0.2001(3) 0.0983(2) 1.0416(2) 0.0398(5) Uani 1 1 d . . . . .
H15 H 0.2132 0.0953 0.9587 0.048 Uiso 1 1 calc R . . . .
C16 C 0.2682(3) 0.3459(2) 0.80093(19) 0.0288(4) Uani 1 1 d . . . . .
C17 C 0.4450(3) 0.3259(2) 0.7537(2) 0.0355(5) Uani 1 1 d . . . . .
H17 H 0.5469 0.3173 0.8039 0.043 Uiso 1 1 calc R . . . .
C18 C 0.4694(3) 0.3187(3) 0.6313(2) 0.0413(5) Uani 1 1 d . . . . .
H18 H 0.5879 0.3050 0.5999 0.050 Uiso 1 1 calc R . . . .
C19 C 0.3196(3) 0.3318(2) 0.5557(2) 0.0390(5) Uani 1 1 d . . . . .
H19 H 0.3371 0.3277 0.4734 0.047 Uiso 1 1 calc R . . . .
C20 C 0.1440(3) 0.3511(2) 0.6026(2) 0.0380(5) Uani 1 1 d . . . . .
H20 H 0.0428 0.3601 0.5516 0.046 Uiso 1 1 calc R . . . .
C21 C 0.1169(3) 0.3573(2) 0.7258(2) 0.0345(5) Uani 1 1 d . . . . .
H21 H -0.0022 0.3691 0.7576 0.041 Uiso 1 1 calc R . . . .


_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 C8 1.718(2) . ?
S1 C11 1.744(2) . ?
N1 C1 1.419(3) . ?
N1 C8 1.308(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.411(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(3) . ?
C6 C7 1.462(3) . ?
C7 C8 1.465(3) . ?
C7 C9 1.358(3) . ?
C9 C10 1.458(3) . ?
C9 C16 1.496(3) . ?
C10 C11 1.409(3) . ?
C10 C15 1.406(3) . ?
C11 C12 1.400(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(3) . ?
C16 C21 1.387(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.393(3) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C11 102.87(10) . . ?
C8 N1 C1 104.38(16) . . ?
C2 C1 N1 126.17(19) . . ?
C2 C1 C6 121.4(2) . . ?
C6 C1 N1 112.39(18) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.77(19) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 105.50(17) . . ?
C5 C6 C1 119.54(19) . . ?
C5 C6 C7 134.96(18) . . ?
C6 C7 C8 102.46(16) . . ?
C9 C7 C6 132.78(18) . . ?
C9 C7 C8 124.76(18) . . ?
N1 C8 S1 121.63(15) . . ?
N1 C8 C7 115.28(18) . . ?
C7 C8 S1 123.09(16) . . ?
C7 C9 C10 121.95(18) . . ?
C7 C9 C16 119.41(18) . . ?
C10 C9 C16 118.63(17) . . ?
C11 C10 C9 123.02(19) . . ?
C15 C10 C9 119.81(19) . . ?
C15 C10 C11 117.17(19) . . ?
C10 C11 S1 124.30(16) . . ?
C12 C11 S1 115.13(16) . . ?
C12 C11 C10 120.6(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
C10 C15 H15 119.0 . . ?
C14 C15 C10 121.9(2) . . ?
C14 C15 H15 119.0 . . ?
C17 C16 C9 119.46(18) . . ?
C21 C16 C9 120.85(18) . . ?
C21 C16 C17 119.68(19) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 119.8(2) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?

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 C11 C12 C13 -179.81(18) . . . . ?
N1 C1 C2 C3 -179.6(2) . . . . ?
N1 C1 C6 C5 179.19(17) . . . . ?
N1 C1 C6 C7 -0.6(2) . . . . ?
C1 N1 C8 S1 179.17(14) . . . . ?
C1 N1 C8 C7 -0.5(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C6 C7 C8 0.3(2) . . . . ?
C1 C6 C7 C9 -179.3(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 C7 179.14(19) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -179.7(2) . . . . ?
C5 C6 C7 C8 -179.5(2) . . . . ?
C5 C6 C7 C9 1.0(4) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C6 C7 C8 S1 -179.51(14) . . . . ?
C6 C7 C8 N1 0.1(2) . . . . ?
C6 C7 C9 C10 179.53(19) . . . . ?
C6 C7 C9 C16 0.5(3) . . . . ?
C7 C9 C10 C11 0.0(3) . . . . ?
C7 C9 C10 C15 179.7(2) . . . . ?
C7 C9 C16 C17 90.1(2) . . . . ?
C7 C9 C16 C21 -88.5(3) . . . . ?
C8 S1 C11 C10 0.3(2) . . . . ?
C8 S1 C11 C12 -179.61(16) . . . . ?
C8 N1 C1 C2 -179.1(2) . . . . ?
C8 N1 C1 C6 0.7(2) . . . . ?
C8 C7 C9 C10 0.0(3) . . . . ?
C8 C7 C9 C16 -179.00(17) . . . . ?
C9 C7 C8 S1 0.1(3) . . . . ?
C9 C7 C8 N1 179.74(18) . . . . ?
C9 C10 C11 S1 -0.3(3) . . . . ?
C9 C10 C11 C12 179.67(19) . . . . ?
C9 C10 C15 C14 179.8(2) . . . . ?
C9 C16 C17 C18 -178.1(2) . . . . ?
C9 C16 C21 C20 177.56(19) . . . . ?
C10 C9 C16 C17 -88.9(2) . . . . ?
C10 C9 C16 C21 92.4(2) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 S1 C8 N1 -179.88(16) . . . . ?
C11 S1 C8 C7 -0.25(18) . . . . ?
C11 C10 C15 C14 -0.4(3) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C10 0.7(4) . . . . ?
C15 C10 C11 S1 -179.98(16) . . . . ?
C15 C10 C11 C12 0.0(3) . . . . ?
C16 C9 C10 C11 179.10(19) . . . . ?
C16 C9 C10 C15 -1.2(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C16 C21 C20 -1.1(3) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C19 C20 C21 C16 0.9(3) . . . . ?
C21 C16 C17 C18 0.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_a
_database_code_depnum_ccdc_archive 'CCDC 1438783'
_audit_update_record             
;
2015-11-25 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;
_audit_creation_date             2015-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N O2 S'
_chemical_formula_sum            'C22 H17 N O2 S'
_chemical_formula_weight         359.42
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.0789(15)
_cell_length_b                   11.6353(15)
_cell_length_c                   16.290(3)
_cell_angle_alpha                93.084(9)
_cell_angle_beta                 106.290(10)
_cell_angle_gamma                115.259(8)
_cell_volume                     1786.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5670
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4850
_cell_measurement_theta_min      2.1493
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blcok
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.41
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20502
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.349
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
scan:
	Number of images: 358
	           Slice: -110.0000 - 69.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.0807
	          2theta: -19.8965
scan:
	Number of images: 336
	           Slice: -110.0000 - 58.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.0807
	          2theta: -19.8965
scan:
	Number of images: 282
	           Slice: -80.0000 - 61.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 40.0807
	          2theta: -19.8965
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             8103
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0243
_diffrn_orient_matrix_UB_12      0.0771
_diffrn_orient_matrix_UB_13      -0.0680
_diffrn_orient_matrix_UB_21      0.0378
_diffrn_orient_matrix_UB_22      -0.0876
_diffrn_orient_matrix_UB_23      -0.0172
_diffrn_orient_matrix_UB_31      -0.0623
_diffrn_orient_matrix_UB_32      -0.0091
_diffrn_orient_matrix_UB_33      -0.0170
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7476
_reflns_number_total             8089
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         8089
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.227
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1651
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N1(H1), C18A(H18A), C22(H22), C10(H10), C12A(H12A), C10A(H10A),
 C11A(H11A), C19A(H19A), C13(H13), C12(H12), C21(H21), C22A(H22A), C13A(H13A),
 C20A(H20A), C11(H11), C4A(H4A), C18(H18), C20(H20), C6(H6), C7(H7), C3A(H3A),
 C6A(H6A), C3(H3), C19(H19), C4(H4), C7A(H7A), C21A(H21A)
2.b Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1(H1B,H1C,H1D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.69145(4) 0.29303(4) 0.42515(3) 0.03039(13) Uani 1 1 d . . . . .
S1 S -0.12707(4) 0.25907(4) 0.08017(3) 0.03192(13) Uani 1 1 d . . . . .
O1A O 1.14648(13) 0.76009(11) 0.37560(7) 0.0327(3) Uani 1 1 d . . . . .
O2A O 0.44004(12) 0.12698(11) 0.32544(8) 0.0327(3) Uani 1 1 d . . . . .
O2 O 0.12171(13) 0.42122(11) 0.18415(8) 0.0346(3) Uani 1 1 d . . . . .
O1 O -0.60521(13) -0.21104(12) 0.10567(8) 0.0369(3) Uani 1 1 d . . . . .
N1A N 0.53817(13) 0.30692(12) 0.26811(8) 0.0248(3) Uani 1 1 d . . . . .
H1A H 0.6164 0.3757 0.2767 0.030 Uiso 1 1 calc R . . . .
N1 N 0.01545(13) 0.24042(12) 0.23899(8) 0.0255(3) Uani 1 1 d . . . . .
H1 H -0.0647 0.1734 0.2295 0.031 Uiso 1 1 calc R . . . .
C9A C 0.42480(15) 0.28375(13) 0.19209(9) 0.0204(3) Uani 1 1 d . . . . .
C14A C 0.45287(15) 0.36798(13) 0.13324(9) 0.0217(3) Uani 1 1 d . . . . .
C17A C 0.84966(15) 0.65024(14) 0.16484(9) 0.0238(3) Uani 1 1 d . . . . .
C17 C -0.30894(16) -0.10818(15) 0.33176(10) 0.0254(3) Uani 1 1 d . . . . .
C9 C 0.12563(15) 0.25948(14) 0.31554(9) 0.0231(3) Uani 1 1 d . . . . .
C15A C 0.59386(16) 0.46828(14) 0.14820(9) 0.0240(3) Uani 1 1 d . . . . .
C18A C 0.88814(17) 0.78173(15) 0.18776(10) 0.0263(3) Uani 1 1 d . . . . .
H18A H 0.8243 0.8066 0.1995 0.032 Uiso 1 1 calc R . . . .
C8A C 0.53649(16) 0.23144(14) 0.32945(10) 0.0245(3) Uani 1 1 d . . . . .
C22 C -0.34483(17) -0.23937(15) 0.31238(10) 0.0285(3) Uani 1 1 d . . . . .
H22 H -0.2765 -0.2638 0.3088 0.034 Uiso 1 1 calc R . . . .
C15 C -0.05022(16) 0.07468(14) 0.35611(9) 0.0252(3) Uani 1 1 d . . . . .
C10 C 0.26462(16) 0.35547(15) 0.33496(10) 0.0289(3) Uani 1 1 d . . . . .
H10 H 0.2869 0.4132 0.2978 0.035 Uiso 1 1 calc R . . . .
C16 C -0.16774(17) -0.00934(15) 0.34425(10) 0.0268(3) Uani 1 1 d . . . . .
C16A C 0.71076(16) 0.55196(15) 0.15798(9) 0.0253(3) Uani 1 1 d . . . . .
C14 C 0.09273(15) 0.17384(14) 0.37349(9) 0.0237(3) Uani 1 1 d . . . . .
C12A C 0.20533(16) 0.25474(16) 0.04279(10) 0.0279(3) Uani 1 1 d . . . . .
H12A H 0.1318 0.2455 -0.0063 0.034 Uiso 1 1 calc R . . . .
C10A C 0.28781(16) 0.18492(14) 0.17506(10) 0.0255(3) Uani 1 1 d . . . . .
H10A H 0.2689 0.1286 0.2135 0.031 Uiso 1 1 calc R . . . .
C11A C 0.17999(16) 0.17075(14) 0.10080(10) 0.0267(3) Uani 1 1 d . . . . .
H11A H 0.0890 0.1040 0.0895 0.032 Uiso 1 1 calc R . . . .
C5 C -0.25971(16) 0.11739(16) 0.09578(10) 0.0276(3) Uani 1 1 d . . . . .
C8 C 0.02251(17) 0.31711(15) 0.17822(10) 0.0270(3) Uani 1 1 d . . . . .
C19A C 1.02181(17) 0.87525(15) 0.19301(10) 0.0299(3) Uani 1 1 d . . . . .
H19A H 1.0473 0.9627 0.2084 0.036 Uiso 1 1 calc R . . . .
C5A C 0.81897(16) 0.43475(15) 0.40499(9) 0.0263(3) Uani 1 1 d . . . . .
C13 C 0.20103(17) 0.18545(16) 0.44779(10) 0.0293(3) Uani 1 1 d . . . . .
H13 H 0.1799 0.1288 0.4858 0.035 Uiso 1 1 calc R . . . .
C12 C 0.33931(17) 0.27994(16) 0.46578(10) 0.0323(4) Uani 1 1 d . . . . .
H12 H 0.4109 0.2862 0.5150 0.039 Uiso 1 1 calc R . . . .
C2A C 1.03712(17) 0.65828(15) 0.38666(10) 0.0263(3) Uani 1 1 d . . . . .
C21 C -0.48223(19) -0.33327(16) 0.29845(11) 0.0344(4) Uani 1 1 d . . . . .
H21 H -0.5062 -0.4206 0.2846 0.041 Uiso 1 1 calc R . . . .
C22A C 0.94696(17) 0.61490(15) 0.14746(11) 0.0297(3) Uani 1 1 d . . . . .
H22A H 0.9228 0.5277 0.1325 0.036 Uiso 1 1 calc R . . . .
C13A C 0.34114(16) 0.35177(14) 0.05930(9) 0.0255(3) Uani 1 1 d . . . . .
H13A H 0.3588 0.4076 0.0205 0.031 Uiso 1 1 calc R . . . .
C20A C 1.11713(17) 0.83912(16) 0.17543(11) 0.0337(4) Uani 1 1 d . . . . .
H20A H 1.2065 0.9021 0.1790 0.040 Uiso 1 1 calc R . . . .
C11 C 0.36973(17) 0.36532(16) 0.40927(11) 0.0315(4) Uani 1 1 d . . . . .
H11 H 0.4621 0.4300 0.4216 0.038 Uiso 1 1 calc R . . . .
C4A C 0.84115(18) 0.55691(16) 0.43929(10) 0.0297(3) Uani 1 1 d . . . . .
H4A H 0.7832 0.5641 0.4688 0.036 Uiso 1 1 calc R . . . .
C2 C -0.48824(17) -0.10776(15) 0.10278(10) 0.0282(3) Uani 1 1 d . . . . .
C18 C -0.41243(17) -0.07325(15) 0.33818(11) 0.0315(4) Uani 1 1 d . . . . .
H18 H -0.3898 0.0139 0.3510 0.038 Uiso 1 1 calc R . . . .
C20 C -0.58342(18) -0.29774(16) 0.30506(11) 0.0353(4) Uani 1 1 d . . . . .
H20 H -0.6754 -0.3611 0.2957 0.042 Uiso 1 1 calc R . . . .
C6 C -0.27534(17) -0.00470(16) 0.06720(11) 0.0318(4) Uani 1 1 d . . . . .
H6 H -0.2090 -0.0111 0.0452 0.038 Uiso 1 1 calc R . . . .
C7 C -0.38775(18) -0.11677(17) 0.07083(11) 0.0330(4) Uani 1 1 d . . . . .
H7 H -0.3961 -0.1976 0.0521 0.040 Uiso 1 1 calc R . . . .
C3A C 0.94918(18) 0.66860(15) 0.43005(10) 0.0300(3) Uani 1 1 d . . . . .
H3A H 0.9626 0.7499 0.4528 0.036 Uiso 1 1 calc R . . . .
C6A C 0.90781(18) 0.42492(16) 0.36136(10) 0.0303(3) Uani 1 1 d . . . . .
H6A H 0.8946 0.3437 0.3387 0.036 Uiso 1 1 calc R . . . .
C1A C 1.1752(2) 0.88719(16) 0.41202(11) 0.0373(4) Uani 1 1 d . . . . .
H1AA H 1.0942 0.9007 0.3862 0.056 Uiso 1 1 calc GR . . . .
H1AB H 1.2557 0.9504 0.4004 0.056 Uiso 1 1 calc GR . . . .
H1AC H 1.1949 0.8959 0.4739 0.056 Uiso 1 1 calc GR . . . .
C3 C -0.47174(18) 0.01442(17) 0.13341(12) 0.0348(4) Uani 1 1 d . . . . .
H3 H -0.5370 0.0209 0.1564 0.042 Uiso 1 1 calc R . . . .
C19 C -0.54869(18) -0.16819(17) 0.32551(12) 0.0375(4) Uani 1 1 d . . . . .
H19 H -0.6170 -0.1447 0.3308 0.045 Uiso 1 1 calc R . . . .
C4 C -0.35927(18) 0.12523(16) 0.12973(11) 0.0329(4) Uani 1 1 d . . . . .
H4 H -0.3495 0.2060 0.1500 0.039 Uiso 1 1 calc R . . . .
C7A C 1.01478(17) 0.53542(16) 0.35198(10) 0.0306(3) Uani 1 1 d . . . . .
H7A H 1.0725 0.5282 0.3223 0.037 Uiso 1 1 calc R . . . .
C21A C 1.07955(17) 0.70961(17) 0.15256(11) 0.0348(4) Uani 1 1 d . . . . .
H21A H 1.1437 0.6856 0.1405 0.042 Uiso 1 1 calc R . . . .
C1 C -0.6246(2) -0.33752(17) 0.07584(12) 0.0401(4) Uani 1 1 d . . . . .
H1B H -0.6358 -0.3490 0.0149 0.060 Uiso 1 1 calc GR . . . .
H1C H -0.7076 -0.4017 0.0844 0.060 Uiso 1 1 calc GR . . . .
H1D H -0.5433 -0.3467 0.1082 0.060 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A C8A 1.7944(16) . ?
S1A C5A 1.7758(16) . ?
S1 C5 1.7689(17) . ?
S1 C8 1.7881(17) . ?
O1A C2A 1.3506(19) . ?
O1A C1A 1.4278(19) . ?
O2A C8A 1.2113(18) . ?
O2 C8 1.2150(19) . ?
O1 C2 1.3554(19) . ?
O1 C1 1.4294(19) . ?
N1A H1A 0.8600 . ?
N1A C9A 1.4094(18) . ?
N1A C8A 1.3641(18) . ?
N1 H1 0.8600 . ?
N1 C9 1.4070(19) . ?
N1 C8 1.364(2) . ?
C9A C14A 1.4087(19) . ?
C9A C10A 1.3938(19) . ?
C14A C15A 1.4358(19) . ?
C14A C13A 1.400(2) . ?
C17A C18A 1.398(2) . ?
C17A C16A 1.4409(19) . ?
C17A C22A 1.396(2) . ?
C17 C22 1.396(2) . ?
C17 C16 1.439(2) . ?
C17 C18 1.397(2) . ?
C9 C10 1.393(2) . ?
C9 C14 1.415(2) . ?
C15A C16A 1.201(2) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.389(2) . ?
C22 H22 0.9300 . ?
C22 C21 1.387(2) . ?
C15 C16 1.200(2) . ?
C15 C14 1.440(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(2) . ?
C14 C13 1.397(2) . ?
C12A H12A 0.9300 . ?
C12A C11A 1.393(2) . ?
C12A C13A 1.379(2) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.385(2) . ?
C11A H11A 0.9300 . ?
C5 C6 1.392(2) . ?
C5 C4 1.398(2) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.382(2) . ?
C5A C4A 1.390(2) . ?
C5A C6A 1.402(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.385(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.391(2) . ?
C2A C3A 1.393(2) . ?
C2A C7A 1.399(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.378(2) . ?
C22A H22A 0.9300 . ?
C22A C21A 1.385(2) . ?
C13A H13A 0.9300 . ?
C20A H20A 0.9300 . ?
C20A C21A 1.378(2) . ?
C11 H11 0.9300 . ?
C4A H4A 0.9300 . ?
C4A C3A 1.392(2) . ?
C2 C7 1.393(2) . ?
C2 C3 1.398(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.382(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(2) . ?
C7 H7 0.9300 . ?
C3A H3A 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C7A 1.380(2) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.378(2) . ?
C19 H19 0.9300 . ?
C4 H4 0.9300 . ?
C7A H7A 0.9300 . ?
C21A H21A 0.9300 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5A S1A C8A 105.84(7) . . ?
C5 S1 C8 106.17(7) . . ?
C2A O1A C1A 117.68(13) . . ?
C2 O1 C1 117.63(13) . . ?
C9A N1A H1A 116.7 . . ?
C8A N1A H1A 116.7 . . ?
C8A N1A C9A 126.69(12) . . ?
C9 N1 H1 116.6 . . ?
C8 N1 H1 116.6 . . ?
C8 N1 C9 126.80(13) . . ?
C14A C9A N1A 117.45(12) . . ?
C10A C9A N1A 122.77(13) . . ?
C10A C9A C14A 119.75(13) . . ?
C9A C14A C15A 120.74(13) . . ?
C13A C14A C9A 118.93(13) . . ?
C13A C14A C15A 120.33(13) . . ?
C18A C17A C16A 120.68(14) . . ?
C22A C17A C18A 119.19(14) . . ?
C22A C17A C16A 120.12(14) . . ?
C22 C17 C16 120.85(14) . . ?
C22 C17 C18 119.16(14) . . ?
C18 C17 C16 119.99(14) . . ?
N1 C9 C14 117.68(13) . . ?
C10 C9 N1 123.05(14) . . ?
C10 C9 C14 119.24(14) . . ?
C16A C15A C14A 177.98(15) . . ?
C17A C18A H18A 120.0 . . ?
C19A C18A C17A 119.94(14) . . ?
C19A C18A H18A 120.0 . . ?
O2A C8A S1A 117.00(11) . . ?
O2A C8A N1A 126.09(14) . . ?
N1A C8A S1A 116.91(11) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.10(15) . . ?
C21 C22 H22 119.9 . . ?
C16 C15 C14 177.71(16) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.32(15) . . ?
C11 C10 H10 119.8 . . ?
C15 C16 C17 178.54(17) . . ?
C15A C16A C17A 176.93(15) . . ?
C9 C14 C15 120.72(13) . . ?
C13 C14 C9 119.25(13) . . ?
C13 C14 C15 120.02(14) . . ?
C11A C12A H12A 120.5 . . ?
C13A C12A H12A 120.5 . . ?
C13A C12A C11A 118.95(14) . . ?
C9A C10A H10A 120.1 . . ?
C11A C10A C9A 119.84(13) . . ?
C11A C10A H10A 120.1 . . ?
C12A C11A H11A 119.4 . . ?
C10A C11A C12A 121.16(14) . . ?
C10A C11A H11A 119.4 . . ?
C6 C5 S1 120.88(12) . . ?
C6 C5 C4 118.57(15) . . ?
C4 C5 S1 120.28(12) . . ?
O2 C8 S1 116.68(12) . . ?
O2 C8 N1 126.04(14) . . ?
N1 C8 S1 117.28(11) . . ?
C18A C19A H19A 119.8 . . ?
C20A C19A C18A 120.36(15) . . ?
C20A C19A H19A 119.8 . . ?
C4A C5A S1A 120.54(12) . . ?
C4A C5A C6A 119.18(15) . . ?
C6A C5A S1A 119.99(12) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 C14 121.04(15) . . ?
C12 C13 H13 119.5 . . ?
C13 C12 H12 120.4 . . ?
C13 C12 C11 119.14(15) . . ?
C11 C12 H12 120.4 . . ?
O1A C2A C3A 124.61(14) . . ?
O1A C2A C7A 115.92(14) . . ?
C3A C2A C7A 119.47(15) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.25(15) . . ?
C20 C21 H21 119.9 . . ?
C17A C22A H22A 120.0 . . ?
C21A C22A C17A 120.04(14) . . ?
C21A C22A H22A 120.0 . . ?
C14A C13A H13A 119.3 . . ?
C12A C13A C14A 121.36(14) . . ?
C12A C13A H13A 119.3 . . ?
C19A C20A H20A 120.0 . . ?
C21A C20A C19A 119.92(15) . . ?
C21A C20A H20A 120.0 . . ?
C10 C11 C12 120.99(15) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C5A C4A H4A 119.6 . . ?
C5A C4A C3A 120.77(14) . . ?
C3A C4A H4A 119.6 . . ?
O1 C2 C7 124.36(14) . . ?
O1 C2 C3 116.13(14) . . ?
C7 C2 C3 119.50(15) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.09(15) . . ?
C19 C18 H18 120.0 . . ?
C21 C20 H20 119.9 . . ?
C21 C20 C19 120.21(15) . . ?
C19 C20 H20 119.9 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.29(15) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 120.2 . . ?
C6 C7 C2 119.61(15) . . ?
C6 C7 H7 120.2 . . ?
C2A C3A H3A 120.1 . . ?
C4A C3A C2A 119.82(14) . . ?
C4A C3A H3A 120.1 . . ?
C5A C6A H6A 119.9 . . ?
C7A C6A C5A 120.17(14) . . ?
C7A C6A H6A 119.9 . . ?
O1A C1A H1AA 109.5 . . ?
O1A C1A H1AB 109.5 . . ?
O1A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.35(15) . . ?
C4 C3 H3 119.8 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.18(15) . . ?
C20 C19 H19 119.9 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.65(15) . . ?
C3 C4 H4 119.7 . . ?
C2A C7A H7A 119.7 . . ?
C6A C7A C2A 120.58(14) . . ?
C6A C7A H7A 119.7 . . ?
C22A C21A H21A 119.7 . . ?
C20A C21A C22A 120.55(15) . . ?
C20A C21A H21A 119.7 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
O1 C1 H1D 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 O2 0.93 2.25 2.860(2) 122.9 .
C10A H10A O2A 0.93 2.24 2.851(2) 122.6 .

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 C5A C4A C3A 174.44(12) . . . . ?
S1A C5A C6A C7A -174.58(12) . . . . ?
S1 C5 C6 C7 -173.18(12) . . . . ?
S1 C5 C4 C3 173.01(13) . . . . ?
O1A C2A C3A C4A -178.63(14) . . . . ?
O1A C2A C7A C6A 178.58(14) . . . . ?
O1 C2 C7 C6 177.05(15) . . . . ?
O1 C2 C3 C4 -177.31(15) . . . . ?
N1A C9A C14A C15A 3.7(2) . . . . ?
N1A C9A C14A C13A -176.82(12) . . . . ?
N1A C9A C10A C11A 177.37(13) . . . . ?
N1 C9 C10 C11 -176.82(14) . . . . ?
N1 C9 C14 C15 -2.8(2) . . . . ?
N1 C9 C14 C13 176.58(12) . . . . ?
C9A N1A C8A S1A -174.10(11) . . . . ?
C9A N1A C8A O2A 5.7(2) . . . . ?
C9A C14A C13A C12A -0.6(2) . . . . ?
C9A C10A C11A C12A -0.7(2) . . . . ?
C14A C9A C10A C11A -0.5(2) . . . . ?
C17A C18A C19A C20A 0.2(2) . . . . ?
C17A C22A C21A C20A 0.5(2) . . . . ?
C17 C22 C21 C20 -1.1(2) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C9 N1 C8 S1 172.28(11) . . . . ?
C9 N1 C8 O2 -7.2(3) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C9 C14 C13 C12 0.6(2) . . . . ?
C15A C14A C13A C12A 178.88(14) . . . . ?
C18A C17A C22A C21A -0.3(2) . . . . ?
C18A C19A C20A C21A 0.0(2) . . . . ?
C8A S1A C5A C4A 99.24(13) . . . . ?
C8A S1A C5A C6A -86.94(13) . . . . ?
C8A N1A C9A C14A -174.37(13) . . . . ?
C8A N1A C9A C10A 7.7(2) . . . . ?
C22 C17 C18 C19 0.1(2) . . . . ?
C22 C21 C20 C19 0.1(3) . . . . ?
C15 C14 C13 C12 179.91(14) . . . . ?
C10 C9 C14 C15 179.09(13) . . . . ?
C10 C9 C14 C13 -1.6(2) . . . . ?
C16 C17 C22 C21 -178.42(14) . . . . ?
C16 C17 C18 C19 179.49(15) . . . . ?
C16A C17A C18A C19A -179.19(13) . . . . ?
C16A C17A C22A C21A 178.84(14) . . . . ?
C14 C9 C10 C11 1.2(2) . . . . ?
C14 C13 C12 C11 0.8(2) . . . . ?
C10A C9A C14A C15A -178.31(13) . . . . ?
C10A C9A C14A C13A 1.2(2) . . . . ?
C11A C12A C13A C14A -0.6(2) . . . . ?
C5 S1 C8 O2 -173.49(12) . . . . ?
C5 S1 C8 N1 7.01(14) . . . . ?
C5 C6 C7 C2 0.7(2) . . . . ?
C8 S1 C5 C6 -94.10(14) . . . . ?
C8 S1 C5 C4 91.92(14) . . . . ?
C8 N1 C9 C10 -6.9(2) . . . . ?
C8 N1 C9 C14 175.03(13) . . . . ?
C19A C20A C21A C22A -0.4(2) . . . . ?
C5A S1A C8A O2A 172.88(12) . . . . ?
C5A S1A C8A N1A -7.34(13) . . . . ?
C5A C4A C3A C2A -0.6(2) . . . . ?
C5A C6A C7A C2A 0.8(2) . . . . ?
C13 C12 C11 C10 -1.2(2) . . . . ?
C21 C20 C19 C18 1.0(3) . . . . ?
C22A C17A C18A C19A 0.0(2) . . . . ?
C13A C12A C11A C10A 1.3(2) . . . . ?
C4A C5A C6A C7A -0.7(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C18 C17 C22 C21 1.0(2) . . . . ?
C6 C5 C4 C3 -1.1(2) . . . . ?
C7 C2 C3 C4 1.9(2) . . . . ?
C3A C2A C7A C6A -0.8(2) . . . . ?
C6A C5A C4A C3A 0.6(2) . . . . ?
C1A O1A C2A C3A 0.9(2) . . . . ?
C1A O1A C2A C7A -178.41(13) . . . . ?
C3 C2 C7 C6 -2.1(2) . . . . ?
C4 C5 C6 C7 0.9(2) . . . . ?
C7A C2A C3A C4A 0.7(2) . . . . ?
C1 O1 C2 C7 1.6(2) . . . . ?
C1 O1 C2 C3 -179.26(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
