# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
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data_AKSsulfide_100k
_database_code_depnum_ccdc_archive 'CCDC 1445051'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;
_audit_creation_date             2015-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N O S'
_chemical_formula_sum            'C23 H17 N O S'
_chemical_formula_weight         355.43
_chemical_absolute_configuration ?
_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      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                   6.132(2)
_cell_length_b                   14.536(5)
_cell_length_c                   19.327(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1722.6(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3219
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessings, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1318
_diffrn_reflns_av_unetI/netI     0.1430
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11726
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_min         3.459
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
scan:
	Number of images: 533
	           Slice: -69.0000 - 90.9000
	     Image width: 0.3000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 334
	           Slice: 4.0000 - 104.2000
	     Image width: 0.3000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 180.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 334
	           Slice: 4.0000 - 104.2000
	     Image width: 0.3000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 90.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.158229
_diffrn_orient_matrix_UB_12      -0.035656
_diffrn_orient_matrix_UB_13      0.017044
_diffrn_orient_matrix_UB_21      -0.014484
_diffrn_orient_matrix_UB_22      0.037634
_diffrn_orient_matrix_UB_23      -0.055737
_diffrn_orient_matrix_UB_31      0.006207
_diffrn_orient_matrix_UB_32      -0.041809
_diffrn_orient_matrix_UB_33      -0.029843
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2163
_reflns_number_total             3922
_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-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.922
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
 Flack x determined using 567 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.0910
_refine_ls_restrained_S_all      1.018
_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)+(0.1367P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2135
_refine_ls_wR_factor_ref         0.2693
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C14(H14), C16(H16), C17(H17), C1(H1A), C20(H20), C23(H23), C6(H6),
 C5(H5), C22(H22), C7(H7), C15(H15), C4(H4), C21(H21), C8(H8), C9(H9)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
S1 S 0.1123(4) 0.80693(14) 0.65069(11) 0.0399(6) Uani 1 1 d . . . . .
O1 O 0.5036(11) 0.8722(4) 0.7703(3) 0.0394(14) Uani 1 1 d . . . . .
H1 H 0.3984 0.8369 0.7619 0.059 Uiso 1 1 calc GR . . . .
N1 N 0.2827(11) 0.7238(4) 0.7719(4) 0.0332(16) Uani 1 1 d . . . . .
C10 C 0.7513(13) 0.7049(5) 0.8904(4) 0.0285(16) Uani 1 1 d . . . . .
C19 C -0.0177(15) 0.8360(6) 0.5190(4) 0.0362(18) Uani 1 1 d . . . . .
H19 H 0.1184 0.8097 0.5064 0.043 Uiso 1 1 calc R . . . .
C12 C 0.1026(13) 0.6736(5) 0.7466(4) 0.0283(16) Uani 1 1 d . . . . .
C3 C 0.6408(13) 0.8311(5) 0.8159(4) 0.0312(17) Uani 1 1 d . . . . .
C11 C 0.9443(13) 0.7535(6) 0.9063(4) 0.0317(18) Uani 1 1 d . . . . .
C14 C -0.1869(13) 0.6613(5) 0.6611(4) 0.0360(18) Uani 1 1 d . . . . .
H14 H -0.2575 0.6841 0.6209 0.043 Uiso 1 1 calc R . . . .
C16 C -0.1588(14) 0.5484(5) 0.7510(4) 0.0345(19) Uani 1 1 d . . . . .
H16 H -0.2112 0.4939 0.7724 0.041 Uiso 1 1 calc R . . . .
C2 C 0.5988(13) 0.7433(5) 0.8406(4) 0.0292(16) Uani 1 1 d . . . . .
C17 C 0.0231(13) 0.5926(5) 0.7775(4) 0.0289(17) Uani 1 1 d . . . . .
H17 H 0.0950 0.5679 0.8169 0.035 Uiso 1 1 calc R . . . .
C13 C -0.0057(14) 0.7065(5) 0.6872(4) 0.0328(17) Uani 1 1 d . . . . .
C1 C 0.4182(12) 0.6899(5) 0.8153(4) 0.0283(16) Uani 1 1 d . . . . .
H1A H 0.3992 0.6285 0.8310 0.034 Uiso 1 1 calc R . . . .
C20 C -0.1598(15) 0.8706(5) 0.4680(4) 0.036(2) Uani 1 1 d . . . . .
H20 H -0.1164 0.8714 0.4208 0.043 Uiso 1 1 calc R . . . .
C23 C -0.2837(14) 0.8749(5) 0.6050(5) 0.039(2) Uani 1 1 d . . . . .
H23 H -0.3266 0.8768 0.6522 0.046 Uiso 1 1 calc R . . . .
C6 C 1.1025(14) 0.7131(5) 0.9509(4) 0.0316(17) Uani 1 1 d . . . . .
H6 H 1.2351 0.7447 0.9598 0.038 Uiso 1 1 calc R . . . .
C5 C 0.9797(15) 0.8421(5) 0.8772(4) 0.0339(18) Uani 1 1 d . . . . .
H5 H 1.1096 0.8747 0.8880 0.041 Uiso 1 1 calc R . . . .
C22 C -0.4243(16) 0.9060(5) 0.5548(4) 0.040(2) Uani 1 1 d . . . . .
H22 H -0.5635 0.9291 0.5676 0.048 Uiso 1 1 calc R . . . .
C7 C 1.0671(13) 0.6306(5) 0.9807(4) 0.0345(19) Uani 1 1 d . . . . .
H7 H 1.1744 0.6042 1.0101 0.041 Uiso 1 1 calc R . . . .
C15 C -0.2651(14) 0.5835(5) 0.6933(4) 0.0348(18) Uani 1 1 d . . . . .
H15 H -0.3919 0.5538 0.6760 0.042 Uiso 1 1 calc R . . . .
C18 C -0.0793(14) 0.8408(5) 0.5874(4) 0.0342(19) Uani 1 1 d . . . . .
C4 C 0.8314(14) 0.8803(5) 0.8346(4) 0.037(2) Uani 1 1 d . . . . .
H4 H 0.8547 0.9405 0.8170 0.044 Uiso 1 1 calc R . . . .
C21 C -0.3659(16) 0.9041(5) 0.4872(5) 0.040(2) Uani 1 1 d . . . . .
H21 H -0.4644 0.9254 0.4528 0.049 Uiso 1 1 calc R . . . .
C8 C 0.8654(15) 0.5826(5) 0.9678(4) 0.0354(19) Uani 1 1 d . . . . .
H8 H 0.8371 0.5254 0.9897 0.043 Uiso 1 1 calc R . . . .
C9 C 0.7147(16) 0.6202(5) 0.9237(4) 0.038(2) Uani 1 1 d . . . . .
H9 H 0.5822 0.5882 0.9153 0.045 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 C13 1.775(8) . ?
S1 C18 1.766(8) . ?
O1 H1 0.8400 . ?
O1 C3 1.357(9) . ?
N1 C12 1.411(9) . ?
N1 C1 1.279(10) . ?
C10 C11 1.411(11) . ?
C10 C2 1.453(11) . ?
C10 C9 1.407(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.409(12) . ?
C19 C18 1.376(11) . ?
C12 C17 1.408(10) . ?
C12 C13 1.409(11) . ?
C3 C2 1.388(10) . ?
C3 C4 1.416(12) . ?
C11 C6 1.425(11) . ?
C11 C5 1.422(11) . ?
C14 H14 0.9500 . ?
C14 C13 1.386(12) . ?
C14 C15 1.377(12) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(11) . ?
C16 C15 1.388(11) . ?
C2 C1 1.438(11) . ?
C17 H17 0.9500 . ?
C1 H1A 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.404(13) . ?
C23 H23 0.9500 . ?
C23 C22 1.374(12) . ?
C23 C18 1.390(12) . ?
C6 H6 0.9500 . ?
C6 C7 1.348(11) . ?
C5 H5 0.9500 . ?
C5 C4 1.347(11) . ?
C22 H22 0.9500 . ?
C22 C21 1.354(12) . ?
C7 H7 0.9500 . ?
C7 C8 1.441(12) . ?
C15 H15 0.9500 . ?
C4 H4 0.9500 . ?
C21 H21 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.371(12) . ?
C9 H9 0.9500 . ?

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
C18 S1 C13 103.5(4) . . ?
C3 O1 H1 109.5 . . ?
C1 N1 C12 122.4(6) . . ?
C11 C10 C2 119.4(7) . . ?
C9 C10 C11 118.2(8) . . ?
C9 C10 C2 122.4(7) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C18 C19 C20 119.0(8) . . ?
C17 C12 N1 123.8(7) . . ?
C17 C12 C13 117.8(7) . . ?
C13 C12 N1 118.3(7) . . ?
O1 C3 C2 120.9(7) . . ?
O1 C3 C4 117.1(6) . . ?
C2 C3 C4 121.9(7) . . ?
C10 C11 C6 119.8(7) . . ?
C10 C11 C5 119.7(7) . . ?
C5 C11 C6 120.6(8) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.3(8) . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C15 120.3(7) . . ?
C15 C16 H16 119.8 . . ?
C3 C2 C10 117.5(7) . . ?
C3 C2 C1 121.4(7) . . ?
C1 C2 C10 121.0(6) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.6(7) . . ?
C16 C17 H17 119.7 . . ?
C12 C13 S1 114.3(6) . . ?
C14 C13 S1 124.9(6) . . ?
C14 C13 C12 120.9(7) . . ?
N1 C1 C2 121.1(7) . . ?
N1 C1 H1A 119.5 . . ?
C2 C1 H1A 119.5 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.7(8) . . ?
C21 C20 H20 120.2 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C18 120.7(9) . . ?
C18 C23 H23 119.6 . . ?
C11 C6 H6 119.5 . . ?
C7 C6 C11 121.1(8) . . ?
C7 C6 H6 119.5 . . ?
C11 C5 H5 119.6 . . ?
C4 C5 C11 120.8(8) . . ?
C4 C5 H5 119.6 . . ?
C23 C22 H22 119.7 . . ?
C21 C22 C23 120.5(9) . . ?
C21 C22 H22 119.7 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(8) . . ?
C8 C7 H7 120.2 . . ?
C14 C15 C16 120.1(8) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C19 C18 S1 117.9(7) . . ?
C19 C18 C23 120.0(8) . . ?
C23 C18 S1 122.0(7) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(7) . . ?
C5 C4 H4 119.8 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(8) . . ?
C22 C21 H21 120.0 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(7) . . ?
C9 C8 H8 120.2 . . ?
C10 C9 H9 119.2 . . ?
C8 C9 C10 121.7(8) . . ?
C8 C9 H9 119.2 . . ?

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
O1 C3 C2 C10 -178.7(7) . . . . ?
O1 C3 C2 C1 4.6(11) . . . . ?
O1 C3 C4 C5 -177.1(7) . . . . ?
N1 C12 C17 C16 178.0(7) . . . . ?
N1 C12 C13 S1 2.3(9) . . . . ?
N1 C12 C13 C14 -178.4(7) . . . . ?
C10 C11 C6 C7 -2.9(11) . . . . ?
C10 C11 C5 C4 -0.1(11) . . . . ?
C10 C2 C1 N1 179.4(7) . . . . ?
C19 C20 C21 C22 2.3(12) . . . . ?
C12 N1 C1 C2 -179.3(6) . . . . ?
C3 C2 C1 N1 -4.1(11) . . . . ?
C11 C10 C2 C3 -6.2(10) . . . . ?
C11 C10 C2 C1 170.4(7) . . . . ?
C11 C10 C9 C8 -3.2(11) . . . . ?
C11 C6 C7 C8 -0.4(11) . . . . ?
C11 C5 C4 C3 -2.5(12) . . . . ?
C2 C10 C11 C6 -175.1(6) . . . . ?
C2 C10 C11 C5 4.4(10) . . . . ?
C2 C10 C9 C8 176.5(7) . . . . ?
C2 C3 C4 C5 0.5(12) . . . . ?
C17 C12 C13 S1 -178.1(6) . . . . ?
C17 C12 C13 C14 1.2(11) . . . . ?
C17 C16 C15 C14 1.5(12) . . . . ?
C13 S1 C18 C19 -113.5(7) . . . . ?
C13 S1 C18 C23 69.1(7) . . . . ?
C13 C12 C17 C16 -1.6(11) . . . . ?
C13 C14 C15 C16 -1.8(12) . . . . ?
C1 N1 C12 C17 15.9(11) . . . . ?
C1 N1 C12 C13 -164.5(7) . . . . ?
C20 C19 C18 S1 -174.1(6) . . . . ?
C20 C19 C18 C23 3.4(12) . . . . ?
C23 C22 C21 C20 -0.3(13) . . . . ?
C6 C11 C5 C4 179.5(7) . . . . ?
C6 C7 C8 C9 1.9(12) . . . . ?
C5 C11 C6 C7 177.6(8) . . . . ?
C22 C23 C18 S1 175.9(6) . . . . ?
C22 C23 C18 C19 -1.4(12) . . . . ?
C7 C8 C9 C10 -0.1(12) . . . . ?
C15 C14 C13 S1 179.7(6) . . . . ?
C15 C14 C13 C12 0.4(12) . . . . ?
C15 C16 C17 C12 0.2(11) . . . . ?
C18 S1 C13 C12 -171.2(6) . . . . ?
C18 S1 C13 C14 9.5(8) . . . . ?
C18 C19 C20 C21 -3.8(12) . . . . ?
C18 C23 C22 C21 -0.1(12) . . . . ?
C4 C3 C2 C10 3.8(11) . . . . ?
C4 C3 C2 C1 -172.8(7) . . . . ?
C9 C10 C11 C6 4.6(10) . . . . ?
C9 C10 C11 C5 -175.8(7) . . . . ?
C9 C10 C2 C3 174.1(7) . . . . ?
C9 C10 C2 C1 -9.3(11) . . . . ?

_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_AKSsulfoxide_100k
_database_code_depnum_ccdc_archive 'CCDC 1445052'
_audit_update_record             
;
2016-01-04 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;
_audit_creation_date             2015-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N O2 S'
_chemical_formula_sum            'C23 H17 N O2 S'
_chemical_formula_weight         371.43
_chemical_absolute_configuration .
_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      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                   5.6260(10)
_cell_length_b                   12.886(2)
_cell_length_c                   24.399(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1768.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3723
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15463
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.162
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
scan:
	Number of images: 583
	           Slice: -69.0000 - 105.9000
	     Image width: 0.3000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 90.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 433
	           Slice: -69.0000 - 60.9000
	     Image width: 0.3000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 500
	           Slice: -32.0000 - 118.0000
	     Image width: 0.3000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 180.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Cryo Loop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.153448
_diffrn_orient_matrix_UB_12      0.085770
_diffrn_orient_matrix_UB_13      -0.026369
_diffrn_orient_matrix_UB_21      0.020498
_diffrn_orient_matrix_UB_22      -0.052939
_diffrn_orient_matrix_UB_23      -0.052910
_diffrn_orient_matrix_UB_31      -0.017631
_diffrn_orient_matrix_UB_32      0.022517
_diffrn_orient_matrix_UB_33      -0.029359
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2975
_reflns_number_total             4029
_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-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 932 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4029
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.083
_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)+(0.0455P)²+0.8448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1418
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C16(H16), C14(H14), C7(H7), C17(H17), C6(H6), C8(H8), C21(H21),
 C4(H4), C1(H1A), C9(H9), C5(H5), C20(H20), C22(H22), C15(H15), C19(H19)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
S1 S 0.5062(2) 0.28371(8) 0.23233(5) 0.0247(3) Uani 1 1 d . . . . .
N1 N 0.4863(7) 0.1122(3) 0.15160(15) 0.0232(8) Uani 1 1 d . . . . .
O1 O 0.7159(6) 0.2231(3) 0.08246(14) 0.0319(8) Uani 1 1 d . . . . .
H1 H 0.6216 0.2106 0.1083 0.048 Uiso 1 1 calc GR . . . .
O2 O 0.4585(7) 0.3432(3) 0.28377(13) 0.0336(9) Uani 1 1 d . . . . .
C2 C 0.7744(8) 0.0396(4) 0.09072(19) 0.0224(10) Uani 1 1 d . . . . .
C23 C 0.5459(9) 0.4431(4) 0.1610(2) 0.0266(11) Uani 1 1 d . . . . .
H23 H 0.6894 0.4554 0.1805 0.032 Uiso 1 1 calc R . . . .
C16 C -0.0207(9) 0.0172(4) 0.2356(2) 0.0297(11) Uani 1 1 d . . . . .
H16 H -0.1291 -0.0392 0.2371 0.036 Uiso 1 1 calc R . . . .
C11 C 1.1132(9) -0.0365(4) 0.0404(2) 0.0283(11) Uani 1 1 d . . . . .
C14 C 0.1195(8) 0.1792(4) 0.2715(2) 0.0262(10) Uani 1 1 d . . . . .
H14 H 0.1105 0.2334 0.2978 0.031 Uiso 1 1 calc R . . . .
C7 C 1.2175(9) -0.2172(4) 0.0488(2) 0.0339(12) Uani 1 1 d . . . . .
H7 H 1.3195 -0.2738 0.0404 0.041 Uiso 1 1 calc R . . . .
C17 C 0.1532(8) 0.0188(4) 0.1963(2) 0.0260(11) Uani 1 1 d . . . . .
H17 H 0.1648 -0.0370 0.1710 0.031 Uiso 1 1 calc R . . . .
C6 C 1.2608(9) -0.1213(4) 0.0280(2) 0.0329(12) Uani 1 1 d . . . . .
H6 H 1.3938 -0.1113 0.0046 0.039 Uiso 1 1 calc R . . . .
C13 C 0.2916(8) 0.1815(3) 0.2312(2) 0.0232(10) Uani 1 1 d . . . . .
C8 C 1.0189(10) -0.2313(4) 0.0830(2) 0.0309(11) Uani 1 1 d . . . . .
H8 H 0.9880 -0.2982 0.0977 0.037 Uiso 1 1 calc R . . . .
C21 C 0.2765(9) 0.4877(4) 0.0891(2) 0.0324(12) Uani 1 1 d . . . . .
H21 H 0.2356 0.5303 0.0588 0.039 Uiso 1 1 calc R . . . .
C3 C 0.8348(9) 0.1366(4) 0.06946(19) 0.0257(11) Uani 1 1 d . . . . .
C10 C 0.9144(8) -0.0491(4) 0.0756(2) 0.0246(11) Uani 1 1 d . . . . .
C4 C 1.0272(10) 0.1478(4) 0.0329(2) 0.0310(11) Uani 1 1 d . . . . .
H4 H 1.0616 0.2139 0.0175 0.037 Uiso 1 1 calc R . . . .
C18 C 0.3994(8) 0.3611(4) 0.1762(2) 0.0245(11) Uani 1 1 d . . . . .
C1 C 0.5914(8) 0.0315(4) 0.13238(19) 0.0241(10) Uani 1 1 d . . . . .
H1A H 0.5482 -0.0351 0.1458 0.029 Uiso 1 1 calc R . . . .
C9 C 0.8692(9) -0.1514(4) 0.0955(2) 0.0266(11) Uani 1 1 d . . . . .
H9 H 0.7336 -0.1639 0.1177 0.032 Uiso 1 1 calc R . . . .
C5 C 1.1632(9) 0.0649(4) 0.0197(2) 0.0309(12) Uani 1 1 d . . . . .
H5 H 1.2954 0.0744 -0.0040 0.037 Uiso 1 1 calc R . . . .
C12 C 0.3131(9) 0.1009(4) 0.1929(2) 0.0248(11) Uani 1 1 d . . . . .
C20 C 0.1290(9) 0.4075(4) 0.1042(2) 0.0307(12) Uani 1 1 d . . . . .
H20 H -0.0148 0.3958 0.0848 0.037 Uiso 1 1 calc R . . . .
C22 C 0.4841(10) 0.5067(4) 0.1178(2) 0.0336(12) Uani 1 1 d . . . . .
H22 H 0.5834 0.5633 0.1078 0.040 Uiso 1 1 calc R . . . .
C15 C -0.0398(9) 0.0974(4) 0.2733(2) 0.0314(12) Uani 1 1 d . . . . .
H15 H -0.1616 0.0961 0.3003 0.038 Uiso 1 1 calc R . . . .
C19 C 0.1904(9) 0.3440(4) 0.1477(2) 0.0291(11) Uani 1 1 d . . . . .
H19 H 0.0887 0.2885 0.1580 0.035 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 O2 1.495(3) . ?
S1 C13 1.788(5) . ?
S1 C18 1.797(5) . ?
N1 C1 1.284(6) . ?
N1 C12 1.409(6) . ?
O1 H1 0.8400 . ?
O1 C3 1.338(6) . ?
C2 C3 1.395(7) . ?
C2 C10 1.437(7) . ?
C2 C1 1.451(6) . ?
C23 H23 0.9500 . ?
C23 C18 1.390(7) . ?
C23 C22 1.380(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.371(7) . ?
C16 C15 1.387(7) . ?
C11 C6 1.406(7) . ?
C11 C10 1.419(7) . ?
C11 C5 1.429(7) . ?
C14 H14 0.9500 . ?
C14 C13 1.380(7) . ?
C14 C15 1.385(7) . ?
C7 H7 0.9500 . ?
C7 C6 1.358(7) . ?
C7 C8 1.405(7) . ?
C17 H17 0.9500 . ?
C17 C12 1.391(7) . ?
C6 H6 0.9500 . ?
C13 C12 1.401(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.365(7) . ?
C21 H21 0.9500 . ?
C21 C20 1.375(7) . ?
C21 C22 1.383(8) . ?
C3 C4 1.410(7) . ?
C10 C9 1.427(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.353(7) . ?
C18 C19 1.384(7) . ?
C1 H1A 0.9500 . ?
C9 H9 0.9500 . ?
C5 H5 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.385(7) . ?
C22 H22 0.9500 . ?
C15 H15 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 C13 105.7(2) . . ?
O2 S1 C18 107.2(2) . . ?
C13 S1 C18 99.8(2) . . ?
C1 N1 C12 119.8(4) . . ?
C3 O1 H1 109.5 . . ?
C3 C2 C10 119.0(4) . . ?
C3 C2 C1 119.8(4) . . ?
C10 C2 C1 120.8(4) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C18 120.4(5) . . ?
C17 C16 H16 119.7 . . ?
C17 C16 C15 120.6(5) . . ?
C15 C16 H16 119.7 . . ?
C6 C11 C10 120.4(5) . . ?
C6 C11 C5 121.2(5) . . ?
C10 C11 C5 118.3(5) . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(5) . . ?
C15 C14 H14 120.2 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.8(5) . . ?
C8 C7 H7 120.6 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C12 121.0(5) . . ?
C12 C17 H17 119.5 . . ?
C11 C6 H6 119.3 . . ?
C7 C6 C11 121.4(5) . . ?
C7 C6 H6 119.3 . . ?
C14 C13 S1 118.6(4) . . ?
C14 C13 C12 121.3(4) . . ?
C12 C13 S1 119.9(4) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.7(5) . . ?
C9 C8 H8 119.1 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.5(5) . . ?
C22 C21 H21 119.8 . . ?
O1 C3 C2 122.4(4) . . ?
O1 C3 C4 116.6(4) . . ?
C2 C3 C4 120.9(4) . . ?
C11 C10 C2 119.7(4) . . ?
C11 C10 C9 116.9(4) . . ?
C9 C10 C2 123.4(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.9 . . ?
C23 C18 S1 115.3(4) . . ?
C19 C18 S1 125.3(4) . . ?
C19 C18 C23 119.4(5) . . ?
N1 C1 C2 121.6(4) . . ?
N1 C1 H1A 119.2 . . ?
C2 C1 H1A 119.2 . . ?
C8 C9 C10 120.7(5) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C5 H5 119.1 . . ?
C4 C5 C11 121.7(5) . . ?
C4 C5 H5 119.1 . . ?
C17 C12 N1 124.6(4) . . ?
C17 C12 C13 117.9(4) . . ?
C13 C12 N1 117.4(4) . . ?
C21 C20 H20 120.0 . . ?
C21 C20 C19 119.9(5) . . ?
C19 C20 H20 120.0 . . ?
C23 C22 C21 119.6(5) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C16 C15 H15 120.2 . . ?
C14 C15 C16 119.7(5) . . ?
C14 C15 H15 120.2 . . ?
C18 C19 C20 120.2(5) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?

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 C13 C12 N1 -8.9(6) . . . . ?
S1 C13 C12 C17 175.0(4) . . . . ?
S1 C18 C19 C20 -178.5(4) . . . . ?
O1 C3 C4 C5 177.0(5) . . . . ?
O2 S1 C13 C14 5.1(4) . . . . ?
O2 S1 C13 C12 -169.2(4) . . . . ?
O2 S1 C18 C23 77.6(4) . . . . ?
O2 S1 C18 C19 -103.3(4) . . . . ?
C2 C3 C4 C5 -2.8(7) . . . . ?
C2 C10 C9 C8 -175.1(5) . . . . ?
C23 C18 C19 C20 0.5(7) . . . . ?
C16 C17 C12 N1 -175.5(4) . . . . ?
C16 C17 C12 C13 0.4(7) . . . . ?
C11 C10 C9 C8 3.1(7) . . . . ?
C14 C13 C12 N1 177.0(4) . . . . ?
C14 C13 C12 C17 0.8(7) . . . . ?
C7 C8 C9 C10 -2.1(7) . . . . ?
C17 C16 C15 C14 -0.5(7) . . . . ?
C6 C11 C10 C2 176.0(5) . . . . ?
C6 C11 C10 C9 -2.2(7) . . . . ?
C6 C11 C5 C4 -177.6(5) . . . . ?
C6 C7 C8 C9 0.2(8) . . . . ?
C13 S1 C18 C23 -172.5(4) . . . . ?
C13 S1 C18 C19 6.6(5) . . . . ?
C13 C14 C15 C16 1.8(7) . . . . ?
C8 C7 C6 C11 0.6(8) . . . . ?
C21 C20 C19 C18 0.2(7) . . . . ?
C3 C2 C10 C11 1.2(7) . . . . ?
C3 C2 C10 C9 179.3(5) . . . . ?
C3 C2 C1 N1 -1.9(7) . . . . ?
C3 C4 C5 C11 2.1(8) . . . . ?
C10 C2 C3 O1 -178.7(4) . . . . ?
C10 C2 C3 C4 1.1(7) . . . . ?
C10 C2 C1 N1 170.6(4) . . . . ?
C10 C11 C6 C7 0.4(8) . . . . ?
C10 C11 C5 C4 0.2(7) . . . . ?
C18 S1 C13 C14 -106.0(4) . . . . ?
C18 S1 C13 C12 79.7(4) . . . . ?
C18 C23 C22 C21 -0.9(7) . . . . ?
C1 N1 C12 C17 -36.0(7) . . . . ?
C1 N1 C12 C13 148.1(5) . . . . ?
C1 C2 C3 O1 -6.0(7) . . . . ?
C1 C2 C3 C4 173.8(4) . . . . ?
C1 C2 C10 C11 -171.4(4) . . . . ?
C1 C2 C10 C9 6.7(7) . . . . ?
C5 C11 C6 C7 178.3(5) . . . . ?
C5 C11 C10 C2 -1.9(7) . . . . ?
C5 C11 C10 C9 179.9(5) . . . . ?
C12 N1 C1 C2 -178.6(4) . . . . ?
C20 C21 C22 C23 1.6(8) . . . . ?
C22 C23 C18 S1 178.9(4) . . . . ?
C22 C23 C18 C19 -0.2(7) . . . . ?
C22 C21 C20 C19 -1.3(8) . . . . ?
C15 C16 C17 C12 -0.6(7) . . . . ?
C15 C14 C13 S1 -176.1(4) . . . . ?
C15 C14 C13 C12 -1.9(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
