# Electronic Supplementary Material (ESI) for Materials Horizons.
# 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).
# 
# 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_2013ncs0176
_database_code_depnum_ccdc_archive 'CCDC 1440981'
_audit_update_record             
;
2015-12-07 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;
_audit_creation_date             2013-03-14
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H30 N4 S4'
_chemical_formula_sum            'C26 H30 N4 S4'
_chemical_formula_weight         526.78
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.5288(11)
_cell_length_b                   8.7463(11)
_cell_length_c                   9.9866(14)
_cell_angle_alpha                105.144(7)
_cell_angle_beta                 93.192(7)
_cell_angle_gamma                117.597(8)
_cell_volume                     623.53(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4324
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.1
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 2011)
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             278
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5158
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.13
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
scan:
	Number of images: 127
	           Slice: -54.0000 - 73.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 14.0000
	             Phi: 25.0000
	             XTD: 45.0100
	          2theta: -17.0180
scan:
	Number of images: 120
	           Slice: -98.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 77.0000
	             XTD: 45.0100
	          2theta: -17.0180
scan:
	Number of images: 100
	           Slice: -78.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -129.0000
	             XTD: 45.0100
	          2theta: -17.0180
scan:
	Number of images: 29
	           Slice: -43.0000 - -14.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 25.0000
	             XTD: 45.0100
	          2theta: -17.0180
scan:
	Number of images: 10
	           Slice: -61.0000 - -51.0000
	     Image width: 1.0000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -15.0000
	             Phi: 128.0000
	             XTD: 45.0100
	          2theta: -17.0180
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.007700
_diffrn_orient_matrix_UB_12      0.124891
_diffrn_orient_matrix_UB_13      -0.049734
_diffrn_orient_matrix_UB_21      0.119041
_diffrn_orient_matrix_UB_22      0.047422
_diffrn_orient_matrix_UB_23      -0.044535
_diffrn_orient_matrix_UB_31      0.007207
_diffrn_orient_matrix_UB_32      -0.018194
_diffrn_orient_matrix_UB_33      -0.103447
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2175
_reflns_number_total             2823
_reflns_threshold_expression     >2σ(I)
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 20112)
;
_computing_data_collection       
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 20112)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b20 (Rigaku, 20112)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2823
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0536P)²+0.1093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1130
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H8A,H8B} of C8, H6 of C6, H5 of C5, {H12A,H12B} of C12, {H11A,H11B} of C11,
   {H10A,H10B} of C10, {H9A,H9B} of C9
 At 1.5 times of:
  {H13A,H13B,H13C} of C13
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.37603(7) 0.22873(7) 0.88220(6) 0.01888(16) Uani 1 1 d . . .
S2 S 0.76830(8) 0.00235(8) 0.66456(6) 0.02189(17) Uani 1 1 d . . .
N1 N 0.7250(2) -0.1312(2) 0.8990(2) 0.0186(4) Uani 1 1 d . . .
N2 N 0.6062(2) 0.1897(2) 0.7004(2) 0.0203(4) Uani 1 1 d . . .
C1 C 0.4565(3) 0.1010(3) 0.9370(2) 0.0171(4) Uani 1 1 d . . .
C2 C 0.6127(3) -0.0619(3) 0.9441(2) 0.0166(4) Uani 1 1 d . . .
C3 C 0.5707(3) 0.0410(3) 0.8775(2) 0.0169(4) Uani 1 1 d . . .
C4 C 0.6402(3) 0.0844(3) 0.7539(2) 0.0174(5) Uani 1 1 d . . .
C5 C 0.7721(3) 0.1173(3) 0.5486(3) 0.0227(5) Uani 1 1 d . . .
H5 H 0.8291 0.1172 0.4719 0.027 Uiso 1 1 calc R . .
C6 C 0.6806(3) 0.2080(3) 0.5843(3) 0.0222(5) Uani 1 1 d . . .
H6 H 0.6692 0.2783 0.5330 0.027 Uiso 1 1 calc R . .
C7 C 0.2586(3) 0.2198(3) 1.0209(2) 0.0185(5) Uani 1 1 d . . .
C8 C 0.1477(3) 0.3120(3) 1.0374(3) 0.0220(5) Uani 1 1 d . . .
H8A H 0.0547 0.2555 0.9520 0.026 Uiso 1 1 calc R . .
H8B H 0.2249 0.4384 1.0444 0.026 Uiso 1 1 calc R . .
C9 C 0.0570(3) 0.3079(3) 1.1637(2) 0.0191(5) Uani 1 1 d . . .
H9A H 0.1475 0.3663 1.2508 0.023 Uiso 1 1 calc R . .
H9B H -0.0239 0.1827 1.1578 0.023 Uiso 1 1 calc R . .
C10 C -0.0492(3) 0.4085(3) 1.1637(2) 0.0191(5) Uani 1 1 d . . .
H10A H 0.0346 0.5334 1.1706 0.023 Uiso 1 1 calc R . .
H10B H -0.1336 0.3523 1.0734 0.023 Uiso 1 1 calc R . .
C11 C -0.1540(3) 0.4117(3) 1.2812(3) 0.0188(5) Uani 1 1 d . . .
H11A H -0.0714 0.4685 1.3725 0.023 Uiso 1 1 calc R . .
H11B H -0.2409 0.2877 1.2744 0.023 Uiso 1 1 calc R . .
C12 C -0.2529(3) 0.5169(3) 1.2712(3) 0.0203(5) Uani 1 1 d . . .
H12A H -0.1647 0.6401 1.2771 0.024 Uiso 1 1 calc R . .
H12B H -0.3334 0.4599 1.1790 0.024 Uiso 1 1 calc R . .
C13 C -0.3619(3) 0.5271(3) 1.3840(3) 0.0259(5) Uani 1 1 d . . .
H13A H -0.4179 0.5969 1.3712 0.039 Uiso 1 1 calc R . .
H13B H -0.2836 0.5846 1.4759 0.039 Uiso 1 1 calc R . .
H13C H -0.4535 0.4061 1.3765 0.039 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 C1 1.734(2) . ?
S1 C7 1.751(2) . ?
S2 C4 1.733(2) . ?
S2 C5 1.713(2) . ?
N1 C2 1.390(3) . ?
N1 C7 1.293(3) 2_657 ?
N2 C4 1.306(3) . ?
N2 C6 1.363(3) . ?
C1 C2 1.406(3) 2_657 ?
C1 C3 1.397(3) . ?
C2 C1 1.406(3) 2_657 ?
C2 C3 1.402(3) . ?
C3 C4 1.462(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.349(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.293(3) 2_657 ?
C7 C8 1.493(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.515(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.528(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.516(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.526(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.510(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C1 S1 C7 88.91(10) . . ?
C5 S2 C4 88.82(11) . . ?
C7 N1 C2 110.25(19) 2_657 . ?
C4 N2 C6 110.89(19) . . ?
C2 C1 S1 109.10(16) 2_657 . ?
C3 C1 S1 128.11(18) . . ?
C3 C1 C2 122.78(19) . 2_657 ?
N1 C2 C1 115.36(19) . 2_657 ?
N1 C2 C3 123.0(2) . . ?
C3 C2 C1 121.64(19) . 2_657 ?
C1 C3 C2 115.6(2) . . ?
C1 C3 C4 121.31(19) . . ?
C2 C3 C4 123.11(19) . . ?
N2 C4 S2 114.27(17) . . ?
N2 C4 C3 121.0(2) . . ?
C3 C4 S2 124.75(16) . . ?
S2 C5 H5 124.8 . . ?
C6 C5 S2 110.42(18) . . ?
C6 C5 H5 124.8 . . ?
N2 C6 H6 122.2 . . ?
C5 C6 N2 115.6(2) . . ?
C5 C6 H6 122.2 . . ?
N1 C7 S1 116.38(16) 2_657 . ?
N1 C7 C8 125.1(2) 2_657 . ?
C8 C7 S1 118.48(17) . . ?
C7 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
C7 C8 C9 116.06(19) . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C8 C9 C10 108.75(18) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 115.61(18) . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 C12 110.85(18) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.72(19) . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 C1 C3 C2 -179.57(17) . . . . ?
S1 C1 C3 C4 0.5(3) . . . . ?
S1 C7 C8 C9 -176.96(16) . . . . ?
S2 C5 C6 N2 -0.3(3) . . . . ?
N1 C2 C3 C1 -179.66(19) . . . . ?
N1 C2 C3 C4 0.3(3) . . . . ?
N1 C7 C8 C9 3.5(3) 2_657 . . . ?
C1 S1 C7 N1 -0.16(19) . . . 2_657 ?
C1 S1 C7 C8 -179.75(18) . . . . ?
C1 C2 C3 C1 0.0(3) 2_657 . . . ?
C1 C2 C3 C4 179.9(2) 2_657 . . . ?
C1 C3 C4 S2 -174.94(17) . . . . ?
C1 C3 C4 N2 4.0(3) . . . . ?
C2 C1 C3 C2 0.0(3) 2_657 . . . ?
C2 C1 C3 C4 -179.9(2) 2_657 . . . ?
C2 C3 C4 S2 5.1(3) . . . . ?
C2 C3 C4 N2 -175.9(2) . . . . ?
C4 S2 C5 C6 0.40(18) . . . . ?
C4 N2 C6 C5 -0.1(3) . . . . ?
C5 S2 C4 N2 -0.50(18) . . . . ?
C5 S2 C4 C3 178.5(2) . . . . ?
C6 N2 C4 S2 0.4(2) . . . . ?
C6 N2 C4 C3 -178.60(19) . . . . ?
C7 S1 C1 C2 0.11(17) . . . 2_657 ?
C7 S1 C1 C3 179.7(2) . . . . ?
C7 N1 C2 C1 0.0(3) 2_657 . . 2_657 ?
C7 N1 C2 C3 179.8(2) 2_657 . . . ?
C7 C8 C9 C10 179.82(19) . . . . ?
C8 C9 C10 C11 178.02(19) . . . . ?
C9 C10 C11 C12 179.50(19) . . . . ?
C10 C11 C12 C13 179.8(2) . . . . ?

####################################################################### 
# 
# 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_2013ncs0210
_database_code_depnum_ccdc_archive 'CCDC 1440982'
_audit_update_record             
;
2015-12-07 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;
_audit_creation_date             2015-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;

# start Validation Reply Form
_vrf_PLAT930_2013ncs0210         
;
PROBLEM: Check Twin Law ( 1 0  0)[ 5 0  2] Estimated BASF       0.17       
RESPONSE: The twin law checked and a refinement made using hklf5 format
data file. The BASF refined to 0.18 but there was no improvement to the model nor
residual electron density peaks and agreement factors were slightly higher.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 N2 O2 S2'
_chemical_formula_sum            'C36 H36 N2 O2 S2'
_chemical_formula_weight         592.79
_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 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1180 0.1170 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.575(19)
_cell_length_b                   7.664(9)
_cell_length_c                   14.393(19)
_cell_angle_alpha                90
_cell_angle_beta                 111.280(14)
_cell_angle_gamma                90
_cell_volume                     1498(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3083
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.6
_cell_measurement_theta_min      2.4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
'CrystalClear-SM Expert 3.1 b21 (Rigaku, 20112)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1462
_diffrn_reflns_av_unetI/netI     0.1068
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13997
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         26.609
_diffrn_reflns_theta_min         2.770
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
scan:
	Number of images: 175
	           Slice: -60.0000 - 115.0000
	     Image width: 1.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 59.6885
	          2theta: 30.1106
scan:
	Number of images: 120
	           Slice: -60.0000 - 60.0000
	     Image width: 1.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -50.0000
	             Phi: 0.0000
	             XTD: 59.6885
	          2theta: 30.1106
scan:
	Number of images: 120
	           Slice: -60.0000 - 60.0000
	     Image width: 1.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -50.0000
	             Phi: 120.0000
	             XTD: 59.6885
	          2theta: 30.1106
scan:
	Number of images: 120
	           Slice: -60.0000 - 60.0000
	     Image width: 1.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -50.0000
	             Phi: 240.0000
	             XTD: 59.6885
	          2theta: 30.1106
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.021616
_diffrn_orient_matrix_UB_12      -0.044142
_diffrn_orient_matrix_UB_13      0.056070
_diffrn_orient_matrix_UB_21      0.119081
_diffrn_orient_matrix_UB_22      0.053188
_diffrn_orient_matrix_UB_23      -0.004034
_diffrn_orient_matrix_UB_31      -0.012028
_diffrn_orient_matrix_UB_32      0.031880
_diffrn_orient_matrix_UB_33      0.065272
_diffrn_radiation_collimation    'Confocal mirrors'
_diffrn_radiation_monochromator  'double crystal silicon'
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   synchrotron
_diffrn_source_type              'DLS beamline I19'
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2286
_reflns_number_total             3408
_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 3.1 b21 (Rigaku, 20112)'
_computing_data_collection       
'CrystalClear-SM Expert 3.1 b21 (Rigaku, 20112)'
_computing_data_reduction        
'CrystalClear-SM Expert 3.1 b21 (Rigaku, 20112)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.919
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.1081
_refine_ls_restrained_S_all      1.097
_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)+(0.1275P)²+6.4063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2753
_refine_ls_wR_factor_ref         0.3062
_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 Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C20(H20)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.64488(10) 1.05887(19) 0.38844(9) 0.0270(4) Uani 1 1 d . . . . .
O13 O 0.2415(3) 0.8324(5) 0.4181(3) 0.0272(8) Uani 1 1 d . . . . .
N4 N 0.4662(3) 0.9440(6) 0.2985(3) 0.0257(10) Uani 1 1 d . . . . .
C1 C 0.4028(4) 0.9359(7) 0.4366(4) 0.0235(11) Uani 1 1 d . . . . .
C2 C 0.5717(4) 1.0324(7) 0.4603(4) 0.0246(11) Uani 1 1 d . . . . .
C3 C 0.4776(4) 0.9707(7) 0.3987(4) 0.0241(11) Uani 1 1 d . . . . .
C5 C 0.5466(4) 0.9848(7) 0.2841(4) 0.0240(11) Uani 1 1 d . . . . .
C6 C 0.5551(4) 0.9742(7) 0.1836(4) 0.0253(11) Uani 1 1 d . . . . .
H6A H 0.5484 1.0936 0.1558 0.030 Uiso 1 1 calc R . . . .
H6B H 0.4987 0.9051 0.1394 0.030 Uiso 1 1 calc R . . . .
C7 C 0.6497(4) 0.8945(7) 0.1794(4) 0.0243(11) Uani 1 1 d . . . . .
H7A H 0.7074 0.9572 0.2261 0.029 Uiso 1 1 calc R . . . .
H7B H 0.6544 0.7706 0.2001 0.029 Uiso 1 1 calc R . . . .
C8 C 0.6498(4) 0.9073(7) 0.0735(4) 0.0245(11) Uani 1 1 d . . . . .
H8A H 0.6394 1.0308 0.0521 0.029 Uiso 1 1 calc R . . . .
H8B H 0.5933 0.8396 0.0286 0.029 Uiso 1 1 calc R . . . .
C9 C 0.7438(4) 0.8419(7) 0.0600(4) 0.0267(11) Uani 1 1 d . . . . .
H9A H 0.8021 0.8933 0.1125 0.032 Uiso 1 1 calc R . . . .
H9B H 0.7480 0.7135 0.0678 0.032 Uiso 1 1 calc R . . . .
C10 C 0.7449(4) 0.8911(8) -0.0428(4) 0.0332(13) Uani 1 1 d . . . . .
H10A H 0.6846 0.8447 -0.0946 0.040 Uiso 1 1 calc R . . . .
H10B H 0.7431 1.0199 -0.0489 0.040 Uiso 1 1 calc R . . . .
C11 C 0.8345(4) 0.8227(10) -0.0624(5) 0.0410(15) Uani 1 1 d . . . . .
H11A H 0.8312 0.8610 -0.1285 0.061 Uiso 1 1 calc GR . . . .
H11B H 0.8352 0.6949 -0.0598 0.061 Uiso 1 1 calc GR . . . .
H11C H 0.8947 0.8682 -0.0116 0.061 Uiso 1 1 calc GR . . . .
C12 C 0.3064(4) 0.8730(7) 0.3711(4) 0.0272(11) Uani 1 1 d . . . . .
C14 C 0.1579(4) 0.7688(8) 0.3443(4) 0.0289(12) Uani 1 1 d . . . . .
C15 C 0.0738(4) 0.7091(8) 0.3584(5) 0.0333(13) Uani 1 1 d . . . . .
H15 H 0.0674 0.7103 0.4217 0.040 Uiso 1 1 calc R . . . .
C16 C -0.0005(4) 0.6475(8) 0.2729(4) 0.0311(13) Uani 1 1 d . . . . .
H16 H -0.0594 0.6040 0.2783 0.037 Uiso 1 1 calc R . . . .
C17 C 0.0088(4) 0.6477(8) 0.1796(5) 0.0361(13) Uani 1 1 d . . . . .
H17 H -0.0441 0.6056 0.1232 0.043 Uiso 1 1 calc R . . . .
C18 C 0.0936(4) 0.7079(8) 0.1672(4) 0.0337(13) Uani 1 1 d . . . . .
H18 H 0.0997 0.7068 0.1037 0.040 Uiso 1 1 calc R . . . .
C19 C 0.1706(4) 0.7712(7) 0.2530(4) 0.0288(12) Uani 1 1 d . . . . .
C20 C 0.2674(4) 0.8395(7) 0.2716(4) 0.0273(11) Uani 1 1 d . . . . .
H20 H 0.2979 0.8575 0.2242 0.033 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 C2 1.746(5) . ?
S1 C5 1.752(5) . ?
O13 C12 1.384(6) . ?
O13 C14 1.382(6) . ?
N4 C3 1.406(7) . ?
N4 C5 1.300(7) . ?
C1 C2 1.415(7) 3_676 ?
C1 C3 1.411(7) . ?
C1 C12 1.460(7) . ?
C2 C1 1.414(7) 3_676 ?
C2 C3 1.416(7) . ?
C5 C6 1.497(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.529(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.528(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.536(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.532(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.527(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C20 1.360(7) . ?
C14 C15 1.390(8) . ?
C14 C19 1.393(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.399(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.419(8) . ?
C19 C20 1.436(8) . ?
C20 H20 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
C2 S1 C5 89.1(3) . . ?
C14 O13 C12 105.8(4) . . ?
C5 N4 C3 110.5(4) . . ?
C2 C1 C12 124.0(5) 3_676 . ?
C3 C1 C2 115.3(5) . 3_676 ?
C3 C1 C12 120.7(5) . . ?
C1 C2 S1 128.1(4) 3_676 . ?
C1 C2 C3 122.7(5) 3_676 . ?
C3 C2 S1 109.2(4) . . ?
N4 C3 C1 123.3(5) . . ?
N4 C3 C2 114.7(4) . . ?
C1 C3 C2 122.0(5) . . ?
N4 C5 S1 116.4(4) . . ?
N4 C5 C6 122.4(5) . . ?
C6 C5 S1 121.2(4) . . ?
C5 C6 H6A 108.1 . . ?
C5 C6 H6B 108.1 . . ?
C5 C6 C7 116.8(4) . . ?
H6A C6 H6B 107.3 . . ?
C7 C6 H6A 108.1 . . ?
C7 C6 H6B 108.1 . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 C6 110.0(4) . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C7 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
C7 C8 C9 115.4(4) . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.3(4) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.8(5) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O13 C12 C1 115.3(4) . . ?
C20 C12 O13 111.9(5) . . ?
C20 C12 C1 132.7(5) . . ?
O13 C14 C15 125.6(5) . . ?
O13 C14 C19 109.8(5) . . ?
C15 C14 C19 124.6(5) . . ?
C14 C15 H15 122.4 . . ?
C14 C15 C16 115.3(5) . . ?
C16 C15 H15 122.4 . . ?
C15 C16 H16 118.9 . . ?
C15 C16 C17 122.2(5) . . ?
C17 C16 H16 118.9 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.6(5) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 121.2 . . ?
C17 C18 C19 117.5(5) . . ?
C19 C18 H18 121.2 . . ?
C14 C19 C18 118.8(5) . . ?
C14 C19 C20 106.7(5) . . ?
C18 C19 C20 134.5(5) . . ?
C12 C20 C19 105.8(5) . . ?
C12 C20 H20 127.1 . . ?
C19 C20 H20 127.1 . . ?

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
C20 H20 N4 0.95 2.39 2.893(8) 113.1 .

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 C2 C3 N4 0.8(6) . . . . ?
S1 C2 C3 C1 179.5(4) . . . . ?
S1 C5 C6 C7 45.1(7) . . . . ?
O13 C12 C20 C19 -0.4(6) . . . . ?
O13 C14 C15 C16 -178.7(5) . . . . ?
O13 C14 C19 C18 178.9(5) . . . . ?
O13 C14 C19 C20 0.2(6) . . . . ?
N4 C5 C6 C7 -136.5(5) . . . . ?
C1 C2 C3 N4 -179.0(5) 3_676 . . . ?
C1 C2 C3 C1 -0.3(9) 3_676 . . . ?
C1 C12 C20 C19 176.9(6) . . . . ?
C2 S1 C5 N4 0.3(5) . . . . ?
C2 S1 C5 C6 178.7(5) . . . . ?
C2 C1 C3 N4 178.9(5) 3_676 . . . ?
C2 C1 C3 C2 0.3(8) 3_676 . . . ?
C2 C1 C12 O13 -4.8(8) 3_676 . . . ?
C2 C1 C12 C20 178.0(6) 3_676 . . . ?
C3 N4 C5 S1 0.2(6) . . . . ?
C3 N4 C5 C6 -178.3(5) . . . . ?
C3 C1 C12 O13 175.8(5) . . . . ?
C3 C1 C12 C20 -1.4(9) . . . . ?
C5 S1 C2 C1 179.2(5) . . . 3_676 ?
C5 S1 C2 C3 -0.6(4) . . . . ?
C5 N4 C3 C1 -179.3(5) . . . . ?
C5 N4 C3 C2 -0.6(7) . . . . ?
C5 C6 C7 C8 -175.4(4) . . . . ?
C6 C7 C8 C9 176.4(4) . . . . ?
C7 C8 C9 C10 -169.4(5) . . . . ?
C8 C9 C10 C11 -177.5(5) . . . . ?
C12 O13 C14 C15 178.9(6) . . . . ?
C12 O13 C14 C19 -0.4(6) . . . . ?
C12 C1 C3 N4 -1.6(8) . . . . ?
C12 C1 C3 C2 179.7(5) . . . . ?
C14 O13 C12 C1 -177.3(5) . . . . ?
C14 O13 C12 C20 0.5(6) . . . . ?
C14 C15 C16 C17 -0.7(9) . . . . ?
C14 C19 C20 C12 0.1(6) . . . . ?
C15 C14 C19 C18 -0.4(9) . . . . ?
C15 C14 C19 C20 -179.1(5) . . . . ?
C15 C16 C17 C18 0.7(10) . . . . ?
C16 C17 C18 C19 -0.5(9) . . . . ?
C17 C18 C19 C14 0.4(9) . . . . ?
C17 C18 C19 C20 178.7(6) . . . . ?
C18 C19 C20 C12 -178.3(6) . . . . ?
C19 C14 C15 C16 0.5(9) . . . . ?

_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_compound10rev1
_database_code_depnum_ccdc_archive 'CCDC 1440983'
_audit_update_record             
;
2015-12-07 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;
_audit_creation_date             2015-12-07
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 N2 S4'
_chemical_formula_sum            'C36 H36 N2 S4'
_chemical_formula_weight         624.91
_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 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1180 0.1170 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.2375(10)
_cell_length_b                   7.3024(6)
_cell_length_c                   28.201(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.461(7)
_cell_angle_gamma                90
_cell_volume                     3095.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4275
_cell_measurement_theta_min      2.6490
_cell_measurement_theta_max      26.5500
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_min  0.33752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lath
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            14285
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.206
_diffrn_reflns_theta_max         24.206
_diffrn_reflns_theta_min         2.773
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  'Synchrotron '
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_radiation_wavelength     0.6889
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2259
_reflns_number_total             2719
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)'
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    ?
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.054
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     601
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0878
_refine_ls_restrained_S_all      1.028
_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)+(0.0785P)²+35.1703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2478
_refine_ls_wR_factor_ref         0.2551
_refine_special_details          
;
 In the crystal structure benzothiphene is disordered and modelled over two sites with
72:28 ratio (FVAR = 0.71851). SIMU, DELU and RIGU restraints were used to maintain 
atomic displacement parameters.
;
_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. Restrained distances
 C6A-C7A
 1.4 with sigma of 0.01
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(S1A)=Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=1-FVAR(1)
 Sof(S1)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(H5)=Sof(C6)=Sof(C7)=Sof(H7)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C2A(H2A), C3A(H3A), C4A(H4A),
 C5A(H5A), C7A(H7A)
7.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
S2 S 0.62127(9) 0.5208(2) 0.53896(5) 0.0382(5) Uani 1 1 d . U . . .
N2 N 0.6826(3) 0.5780(7) 0.45961(16) 0.0357(10) Uani 1 1 d . U . . .
C8 C 0.7017(3) 0.1359(8) 0.5930(2) 0.0367(12) Uani 1 1 d . U . . .
C9 C 0.7237(3) 0.1953(8) 0.54622(19) 0.0352(11) Uani 1 1 d . U . . .
C10 C 0.6949(3) 0.3567(8) 0.52237(19) 0.0354(11) Uani 1 1 d . U . . .
C11 C 0.7194(3) 0.4145(8) 0.47809(19) 0.0349(12) Uani 1 1 d . U . . .
C12 C 0.6302(3) 0.6497(8) 0.4871(2) 0.0364(12) Uani 1 1 d . U . . .
C13 C 0.5802(4) 0.8227(8) 0.4760(2) 0.0398(13) Uani 1 1 d . U . . .
H13A H 0.6007 0.9128 0.5017 0.048 Uiso 1 1 calc R . . . .
H13B H 0.5163 0.7992 0.4762 0.048 Uiso 1 1 calc R . . . .
C14 C 0.5908(4) 0.9060(9) 0.4276(2) 0.0404(13) Uani 1 1 d . U . . .
H14A H 0.6550 0.9197 0.4263 0.048 Uiso 1 1 calc R . . . .
H14B H 0.5654 0.8206 0.4017 0.048 Uiso 1 1 calc R . . . .
C15 C 0.5462(3) 1.0898(9) 0.4185(2) 0.0389(12) Uani 1 1 d . U . . .
H15A H 0.5691 1.1725 0.4456 0.047 Uiso 1 1 calc R . . . .
H15B H 0.4815 1.0743 0.4181 0.047 Uiso 1 1 calc R . . . .
C16 C 0.5603(4) 1.1808(9) 0.3716(2) 0.0416(13) Uani 1 1 d . U . . .
H16A H 0.6247 1.1798 0.3699 0.050 Uiso 1 1 calc R . . . .
H16B H 0.5297 1.1071 0.3443 0.050 Uiso 1 1 calc R . . . .
C17 C 0.5270(4) 1.3753(9) 0.3659(2) 0.0459(14) Uani 1 1 d . U . . .
H17A H 0.5527 1.4459 0.3948 0.055 Uiso 1 1 calc R . . . .
H17B H 0.4615 1.3749 0.3641 0.055 Uiso 1 1 calc R . . . .
C18 C 0.5497(5) 1.4722(10) 0.3215(2) 0.0544(16) Uani 1 1 d . U . . .
H18A H 0.5221 1.4067 0.2925 0.082 Uiso 1 1 calc GR . . . .
H18B H 0.6145 1.4738 0.3230 0.082 Uiso 1 1 calc GR . . . .
H18C H 0.5273 1.5981 0.3205 0.082 Uiso 1 1 calc GR . . . .
S1 S 0.6602(2) 0.2979(4) 0.63043(11) 0.0432(9) Uani 0.719(8) 1 d . U P A 1
C1 C 0.6550(15) 0.131(3) 0.6747(6) 0.041(2) Uani 0.719(8) 1 d . U P A 1
C2 C 0.6279(9) 0.1558(19) 0.7196(4) 0.050(3) Uani 0.719(8) 1 d . U P A 1
H2 H 0.6083 0.2720 0.7288 0.060 Uiso 0.719(8) 1 calc R . P A 1
C3 C 0.6306(7) 0.008(2) 0.7495(4) 0.051(3) Uani 0.719(8) 1 d . U P A 1
H3 H 0.6126 0.0218 0.7800 0.061 Uiso 0.719(8) 1 calc R . P A 1
C4 C 0.6594(7) -0.1626(19) 0.7361(5) 0.052(2) Uani 0.719(8) 1 d . U P A 1
H4 H 0.6608 -0.2629 0.7577 0.062 Uiso 0.719(8) 1 calc R . P A 1
C5 C 0.6862(8) -0.1888(18) 0.6916(4) 0.048(2) Uani 0.719(8) 1 d . U P A 1
H5 H 0.7058 -0.3057 0.6829 0.057 Uiso 0.719(8) 1 calc R . P A 1
C6 C 0.6838(16) -0.040(3) 0.6601(6) 0.041(3) Uani 0.719(8) 1 d . U P A 1
C7 C 0.7072(11) -0.031(2) 0.6130(6) 0.045(3) Uani 0.719(8) 1 d . U P A 1
H7 H 0.7253 -0.1352 0.5970 0.054 Uiso 0.719(8) 1 calc R . P A 1
S1A S 0.7211(7) -0.0886(12) 0.6153(3) 0.0407(19) Uani 0.281(8) 1 d . U P A 2
C1A C 0.682(4) -0.030(8) 0.6679(16) 0.039(5) Uani 0.281(8) 1 d . U P A 2
C2A C 0.672(2) -0.160(4) 0.7061(13) 0.043(5) Uani 0.281(8) 1 d . U P A 2
H2A H 0.6848 -0.2865 0.7035 0.052 Uiso 0.281(8) 1 calc R . P A 2
C3A C 0.6425(19) -0.088(5) 0.7464(10) 0.041(5) Uani 0.281(8) 1 d . U P A 2
H3A H 0.6371 -0.1659 0.7728 0.049 Uiso 0.281(8) 1 calc R . P A 2
C4A C 0.6204(19) 0.100(4) 0.7481(11) 0.044(5) Uani 0.281(8) 1 d . U P A 2
H4A H 0.6011 0.1438 0.7763 0.052 Uiso 0.281(8) 1 calc R . P A 2
C5A C 0.625(2) 0.222(4) 0.7118(11) 0.042(5) Uani 0.281(8) 1 d . U P A 2
H5A H 0.6073 0.3463 0.7141 0.051 Uiso 0.281(8) 1 calc R . P A 2
C6A C 0.659(4) 0.152(7) 0.6685(15) 0.039(5) Uani 0.281(8) 1 d D U P A 2
C7A C 0.672(2) 0.246(5) 0.6270(11) 0.039(5) Uani 0.281(8) 1 d D U P A 2
H7A H 0.6625 0.3738 0.6227 0.046 Uiso 0.281(8) 1 calc R . P A 2


_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
S2 C10 1.756(6) . ?
S2 C12 1.763(6) . ?
N2 C11 1.384(8) . ?
N2 C12 1.310(7) . ?
C8 C9 1.480(8) . ?
C8 S1 1.769(6) . ?
C8 C7 1.336(16) . ?
C8 S1A 1.764(10) . ?
C8 C7A 1.38(3) . ?
C9 C10 1.392(8) . ?
C9 C11 1.435(7) 7_656 ?
C10 C11 1.425(8) . ?
C11 C9 1.435(7) 7_656 ?
C12 C13 1.482(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.526(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.507(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.528(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.508(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.527(9) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
S1 C1 1.758(12) . ?
C1 C2 1.405(19) . ?
C1 C6 1.41(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.368(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.40(2) . ?
C6 C7 1.43(2) . ?
C7 H7 0.9500 . ?
S1A C1A 1.74(4) . ?
C1A C2A 1.47(6) . ?
C1A C6A 1.37(8) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.39(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.42(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.37(4) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.50(5) . ?
C6A C7A 1.400(10) . ?
C7A H7A 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
C10 S2 C12 90.2(3) . . ?
C12 N2 C11 111.8(5) . . ?
C9 C8 S1 119.4(5) . . ?
C9 C8 S1A 122.8(5) . . ?
C7 C8 C9 129.3(8) . . ?
C7 C8 S1 111.2(8) . . ?
C7A C8 C9 126.6(13) . . ?
C7A C8 S1A 110.4(13) . . ?
C10 C9 C8 125.4(5) . . ?
C10 C9 C11 114.2(5) . 7_656 ?
C11 C9 C8 120.4(5) 7_656 . ?
C9 C10 S2 127.9(4) . . ?
C9 C10 C11 124.5(5) . . ?
C11 C10 S2 107.6(4) . . ?
N2 C11 C9 122.8(5) . 7_656 ?
N2 C11 C10 115.9(5) . . ?
C10 C11 C9 121.3(5) . 7_656 ?
N2 C12 S2 114.5(4) . . ?
N2 C12 C13 123.9(5) . . ?
C13 C12 S2 121.6(4) . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C12 C13 C14 113.7(5) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 C13 113.3(5) . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C14 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C14 C15 C16 114.3(5) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 C15 114.1(5) . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C16 C17 C18 113.9(5) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 S1 C8 91.2(7) . . ?
C2 C1 S1 127.1(14) . . ?
C2 C1 C6 122.1(13) . . ?
C6 C1 S1 110.8(12) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.0(13) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(11) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(11) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(12) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 111.4(17) . . ?
C5 C6 C1 118.5(12) . . ?
C5 C6 C7 130.1(16) . . ?
C8 C7 C6 115.3(15) . . ?
C8 C7 H7 122.4 . . ?
C6 C7 H7 122.4 . . ?
C1A S1A C8 91(2) . . ?
C2A C1A S1A 124(4) . . ?
C6A C1A S1A 112(3) . . ?
C6A C1A C2A 124(3) . . ?
C1A C2A H2A 121.8 . . ?
C3A C2A C1A 116(3) . . ?
C3A C2A H2A 121.8 . . ?
C2A C3A H3A 119.9 . . ?
C2A C3A C4A 120(3) . . ?
C4A C3A H3A 119.9 . . ?
C3A C4A H4A 117.7 . . ?
C5A C4A C3A 125(3) . . ?
C5A C4A H4A 117.7 . . ?
C4A C5A H5A 121.6 . . ?
C4A C5A C6A 117(3) . . ?
C6A C5A H5A 121.6 . . ?
C1A C6A C5A 118(3) . . ?
C1A C6A C7A 113(4) . . ?
C7A C6A C5A 129(4) . . ?
C8 C7A C6A 114(3) . . ?
C8 C7A H7A 123.1 . . ?
C6A C7A H7A 123.1 . . ?

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
S2 C10 C11 N2 0.6(6) . . . . ?
S2 C10 C11 C9 -177.2(4) . . . 7_656 ?
S2 C12 C13 C14 -175.3(4) . . . . ?
N2 C12 C13 C14 3.4(8) . . . . ?
C8 C9 C10 S2 -4.3(8) . . . . ?
C8 C9 C10 C11 177.7(5) . . . . ?
C8 S1 C1 C2 178.6(19) . . . . ?
C8 S1 C1 C6 -0.3(17) . . . . ?
C8 S1A C1A C2A 176(5) . . . . ?
C8 S1A C1A C6A -2(5) . . . . ?
C9 C8 S1 C1 -178.8(9) . . . . ?
C9 C8 C7 C6 177.6(13) . . . . ?
C9 C8 S1A C1A 178(2) . . . . ?
C9 C8 C7A C6A -179(3) . . . . ?
C9 C10 C11 N2 179.0(5) . . . . ?
C9 C10 C11 C9 1.2(9) . . . 7_656 ?
C10 S2 C12 N2 0.3(4) . . . . ?
C10 S2 C12 C13 179.2(5) . . . . ?
C11 N2 C12 S2 0.0(6) . . . . ?
C11 N2 C12 C13 -178.8(5) . . . . ?
C11 C9 C10 S2 176.9(4) 7_656 . . . ?
C11 C9 C10 C11 -1.1(9) 7_656 . . . ?
C12 S2 C10 C9 -178.8(5) . . . . ?
C12 S2 C10 C11 -0.5(4) . . . . ?
C12 N2 C11 C9 177.4(5) . . . 7_656 ?
C12 N2 C11 C10 -0.4(7) . . . . ?
C12 C13 C14 C15 -175.1(5) . . . . ?
C13 C14 C15 C16 176.7(5) . . . . ?
C14 C15 C16 C17 -171.7(5) . . . . ?
C15 C16 C17 C18 174.0(5) . . . . ?
S1 C8 C9 C10 -17.1(8) . . . . ?
S1 C8 C9 C11 161.6(4) . . . 7_656 ?
S1 C8 C7 C6 -3.3(19) . . . . ?
S1 C1 C2 C3 -178.5(15) . . . . ?
S1 C1 C6 C5 178.4(15) . . . . ?
S1 C1 C6 C7 -1(3) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C1 C6 C7 C8 3(3) . . . . ?
C2 C1 C6 C5 -1(3) . . . . ?
C2 C1 C6 C7 179.7(19) . . . . ?
C2 C3 C4 C5 -0.2(16) . . . . ?
C3 C4 C5 C6 -0.1(18) . . . . ?
C4 C5 C6 C1 0(3) . . . . ?
C4 C5 C6 C7 -180(2) . . . . ?
C5 C6 C7 C8 -176.7(18) . . . . ?
C6 C1 C2 C3 0(3) . . . . ?
C7 C8 C9 C10 161.9(11) . . . . ?
C7 C8 C9 C11 -19.4(13) . . . 7_656 ?
C7 C8 S1 C1 2.0(12) . . . . ?
S1A C8 C9 C10 166.7(6) . . . . ?
S1A C8 C9 C11 -14.6(8) . . . 7_656 ?
S1A C8 C7A C6A -5(4) . . . . ?
S1A C1A C2A C3A 178(4) . . . . ?
S1A C1A C6A C5A -180(4) . . . . ?
S1A C1A C6A C7A -1(7) . . . . ?
C1A C2A C3A C4A 3(5) . . . . ?
C1A C6A C7A C8 4(7) . . . . ?
C2A C1A C6A C5A 3(9) . . . . ?
C2A C1A C6A C7A -178(5) . . . . ?
C2A C3A C4A C5A 1(5) . . . . ?
C3A C4A C5A C6A -2(5) . . . . ?
C4A C5A C6A C1A 0(7) . . . . ?
C4A C5A C6A C7A -178(5) . . . . ?
C5A C6A C7A C8 -178(4) . . . . ?
C6A C1A C2A C3A -5(8) . . . . ?
C7A C8 C9 C10 -20(2) . . . . ?
C7A C8 C9 C11 159(2) . . . 7_656 ?
C7A C8 S1A C1A 4(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_2013ncs0660
_database_code_depnum_ccdc_archive 'CCDC 1440984'
_audit_update_record             
;
2015-12-07 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;
_audit_creation_date             2015-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
# start Validation Reply Form
_vrf_RFACR01_2013ncs0660         
;
PROBLEM: The value of the weighted R factor is > 0.35
RESPONSE: The crystal was small and quite weakly diffracting. Data
were also collected at Diamond Light Source in an attempt to obtain
a better quality dataset but no improvement obtained.
;
_vrf_PLAT026_2013ncs0660         
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         37 %     
RESPONSE: see above
;
_vrf_PLAT084_2013ncs0660         
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.44 Report
RESPONSE: see above
;
_vrf_PLAT340_2013ncs0660         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01906 Ang.  
RESPONSE: see above
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H34 N4 O2 S2'
_chemical_formula_sum            'C34 H34 N4 O2 S2'
_chemical_formula_weight         594.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_symmetry_Int_Tables_number      14
_cell_length_a                   14.526(2)
_cell_length_b                   5.1215(7)
_cell_length_c                   20.577(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.041(8)
_cell_angle_gamma                90
_cell_volume                     1447.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8189
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      3.0
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.617
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.148
_diffrn_reflns_av_unetI/netI     0.260
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16020
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.058
_diffrn_reflns_theta_max         25.058
_diffrn_reflns_theta_min         3.023
_diffrn_reflns_transf_matrix_11  0.049974
_diffrn_reflns_transf_matrix_12  -0.001924
_diffrn_reflns_transf_matrix_13  0.011045
_diffrn_reflns_transf_matrix_21  -0.019666
_diffrn_reflns_transf_matrix_22  -0.184591
_diffrn_reflns_transf_matrix_23  0.056834
_diffrn_reflns_transf_matrix_31  0.036297
_diffrn_reflns_transf_matrix_32  -0.021975
_diffrn_reflns_transf_matrix_33  -0.058814
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
scan:
	Number of images: 133
	           Slice: -60.0000 - 73.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 14.0000
	             Phi: -180.0000
	             XTD: 44.9826
	          2theta: -17.1738
scan:
	Number of images: 120
	           Slice: -98.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -129.0000
	             XTD: 44.9826
	          2theta: -17.1738
scan:
	Number of images: 104
	           Slice: -82.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 25.0000
	             XTD: 44.9826
	          2theta: -17.1738
scan:
	Number of images: 34
	           Slice: -44.0000 - -10.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -180.0000
	             XTD: 44.9826
	          2theta: -17.1738
scan:
	Number of images: 10
	           Slice: 0.0000 - 10.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -44.0000
	             Phi: -129.0000
	             XTD: 44.9826
	          2theta: -17.1738
scan:
	Number of images: 133
	           Slice: -60.0000 - 73.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 14.0000
	             Phi: 77.0000
	             XTD: 44.9826
	          2theta: -17.1738
scan:
	Number of images: 21
	           Slice: -98.0000 - -77.0000
	     Image width: 1.0000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 128.0000
	             XTD: 44.9826
	          2theta: -17.1738
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.049974
_diffrn_orient_matrix_UB_12      -0.001924
_diffrn_orient_matrix_UB_13      0.011045
_diffrn_orient_matrix_UB_21      -0.019666
_diffrn_orient_matrix_UB_22      -0.184591
_diffrn_orient_matrix_UB_23      0.056834
_diffrn_orient_matrix_UB_31      0.036297
_diffrn_orient_matrix_UB_32      -0.021975
_diffrn_orient_matrix_UB_33      -0.058814
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                938
_reflns_number_total             2550
_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 3.1 b27 (Rigaku, 20112)
;
_computing_data_collection       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     291
_refine_ls_R_factor_all          0.3045
_refine_ls_R_factor_gt           0.1450
_refine_ls_restrained_S_all      1.101
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3462
_refine_ls_wR_factor_ref         0.4364
_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. Restrained distances
 C5-C6 = C7-C6 = C7-C8 = C8-C9 = C9-C10 = C11-C10
 1.51 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.1 and sigma
for terminal atoms of 0.2
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18)
5.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.69033(19) -0.2628(7) 0.49848(12) 0.1103(15) Uani 1 1 d . U . . .
O13 O 0.4632(4) 0.4638(17) 0.3492(3) 0.102(2) Uani 1 1 d . U . . .
N2 N 0.6117(5) 0.123(2) 0.4132(3) 0.090(3) Uani 1 1 d . U . . .
N20 N 0.3520(5) 0.559(2) 0.4008(3) 0.103(3) Uani 1 1 d . U . . .
C1 C 0.4644(6) 0.207(2) 0.4494(4) 0.097(3) Uani 1 1 d . U . . .
C2 C 0.5504(7) 0.068(3) 0.4553(4) 0.099(3) Uani 1 1 d . U . . .
C3 C 0.5849(7) -0.130(3) 0.5040(4) 0.098(3) Uani 1 1 d . U . . .
C5 C 0.6836(7) -0.041(3) 0.4341(4) 0.103(3) Uani 1 1 d D U . . .
C6 C 0.7624(7) -0.040(3) 0.4007(6) 0.121(4) Uani 1 1 d D U . . .
H6A H 0.7957 -0.2119 0.4091 0.145 Uiso 1 1 calc R . . . .
H6B H 0.7313 -0.0209 0.3504 0.145 Uiso 1 1 calc R . . . .
C7 C 0.8373(9) 0.170(3) 0.4257(7) 0.129(4) Uani 1 1 d D U . . .
H7A H 0.8739 0.1437 0.4750 0.155 Uiso 1 1 calc R . . . .
H7B H 0.8052 0.3427 0.4201 0.155 Uiso 1 1 calc R . . . .
C8 C 0.9070(10) 0.159(3) 0.3839(8) 0.172(6) Uani 1 1 d D U . . .
H8A H 0.9443 -0.0065 0.3945 0.207 Uiso 1 1 calc R . . . .
H8B H 0.8684 0.1570 0.3343 0.207 Uiso 1 1 calc R . . . .
C9 C 0.9765(11) 0.381(3) 0.3977(8) 0.168(5) Uani 1 1 d D U . . .
H9A H 1.0107 0.4024 0.4476 0.201 Uiso 1 1 calc R . . . .
H9B H 0.9428 0.5464 0.3790 0.201 Uiso 1 1 calc R . . . .
C10 C 1.0468(14) 0.302(5) 0.3603(11) 0.230(9) Uani 1 1 d D U . . .
H10A H 1.1015 0.1955 0.3897 0.276 Uiso 1 1 calc R . . . .
H10B H 1.0136 0.2063 0.3171 0.276 Uiso 1 1 calc R . . . .
C11 C 1.0786(17) 0.562(5) 0.3471(12) 0.253(10) Uani 1 1 d D U . . .
H11A H 1.1207 0.5468 0.3185 0.379 Uiso 1 1 calc GR . . . .
H11B H 1.1149 0.6455 0.3909 0.379 Uiso 1 1 calc GR . . . .
H11C H 1.0216 0.6687 0.3231 0.379 Uiso 1 1 calc GR . . . .
C12 C 0.4263(7) 0.413(3) 0.4018(4) 0.094(3) Uani 1 1 d . U . . .
C14 C 0.4070(7) 0.669(3) 0.3144(4) 0.100(3) Uani 1 1 d . U . . .
C15 C 0.4135(8) 0.794(3) 0.2551(4) 0.109(3) Uani 1 1 d . U . . .
H15 H 0.4607 0.7474 0.2343 0.130 Uiso 1 1 calc R . . . .
C16 C 0.3479(7) 0.982(3) 0.2305(5) 0.107(4) Uani 1 1 d . U . . .
H16 H 0.3486 1.0695 0.1899 0.129 Uiso 1 1 calc R . . . .
C17 C 0.2782(7) 1.059(3) 0.2601(5) 0.112(4) Uani 1 1 d . U . . .
H17 H 0.2346 1.1984 0.2410 0.135 Uiso 1 1 calc R . . . .
C18 C 0.2743(7) 0.927(3) 0.3187(4) 0.108(3) Uani 1 1 d . U . . .
H18 H 0.2276 0.9727 0.3400 0.129 Uiso 1 1 calc R . . . .
C19 C 0.3397(7) 0.728(3) 0.3446(4) 0.102(3) Uani 1 1 d . 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 C3 1.713(10) . ?
S1 C5 1.725(12) . ?
O13 C12 1.379(10) . ?
O13 C14 1.379(12) . ?
N2 C2 1.456(11) . ?
N2 C5 1.297(12) . ?
N20 C12 1.306(12) . ?
N20 C19 1.407(13) . ?
C1 C2 1.408(13) . ?
C1 C3 1.428(12) 3_656 ?
C1 C12 1.423(15) . ?
C2 C3 1.399(15) . ?
C3 C1 1.428(12) 3_656 ?
C5 C6 1.515(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.498(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.528(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.488(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.521(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.466(10) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C14 C15 1.407(13) . ?
C14 C19 1.353(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.333(14) . ?
C16 H16 0.9500 . ?
C16 C17 1.399(13) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(14) . ?
C18 H18 0.9500 . ?
C18 C19 1.376(15) . ?

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
C3 S1 C5 87.8(5) . . ?
C14 O13 C12 103.6(7) . . ?
C5 N2 C2 105.2(8) . . ?
C12 N20 C19 104.3(8) . . ?
C2 C1 C3 115.3(10) . 3_656 ?
C2 C1 C12 124.7(9) . . ?
C12 C1 C3 120.0(9) . 3_656 ?
C1 C2 N2 123.3(10) . . ?
C3 C2 N2 114.8(9) . . ?
C3 C2 C1 121.9(8) . . ?
C1 C3 S1 126.1(9) 3_656 . ?
C2 C3 S1 111.1(7) . . ?
C2 C3 C1 122.8(9) . 3_656 ?
N2 C5 S1 121.1(6) . . ?
N2 C5 C6 119.7(10) . . ?
C6 C5 S1 119.1(9) . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 C5 114.7(9) . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C6 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
C6 C7 C8 108.7(10) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 C7 113.4(12) . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C8 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C8 C9 C10 102.9(13) . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 H9A 111.2 . . ?
C10 C9 H9B 111.2 . . ?
C9 C10 H10A 112.0 . . ?
C9 C10 H10B 112.0 . . ?
H10A C10 H10B 109.7 . . ?
C11 C10 C9 98.8(16) . . ?
C11 C10 H10A 112.0 . . ?
C11 C10 H10B 112.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O13 C12 C1 121.0(9) . . ?
N20 C12 O13 114.2(9) . . ?
N20 C12 C1 124.7(8) . . ?
O13 C14 C15 127.0(9) . . ?
C19 C14 O13 108.9(9) . . ?
C19 C14 C15 124.0(11) . . ?
C14 C15 H15 122.7 . . ?
C16 C15 C14 114.6(10) . . ?
C16 C15 H15 122.7 . . ?
C15 C16 H16 117.7 . . ?
C15 C16 C17 124.6(10) . . ?
C17 C16 H16 117.7 . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C18 118.4(11) . . ?
C18 C17 H17 120.8 . . ?
C17 C18 H18 120.8 . . ?
C19 C18 C17 118.4(10) . . ?
C19 C18 H18 120.8 . . ?
C14 C19 N20 108.9(10) . . ?
C14 C19 C18 119.9(10) . . ?
C18 C19 N20 131.3(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 C5 C6 C7 -101.2(12) . . . . ?
O13 C14 C15 C16 177.9(10) . . . . ?
O13 C14 C19 N20 0.3(13) . . . . ?
O13 C14 C19 C18 -179.7(9) . . . . ?
N2 C2 C3 S1 -1.9(12) . . . . ?
N2 C2 C3 C1 178.7(9) . . . 3_656 ?
N2 C5 C6 C7 79.7(14) . . . . ?
C1 C2 C3 S1 179.8(8) . . . . ?
C1 C2 C3 C1 0.5(18) . . . 3_656 ?
C2 N2 C5 S1 0.5(12) . . . . ?
C2 N2 C5 C6 179.6(9) . . . . ?
C2 C1 C12 O13 11.0(16) . . . . ?
C2 C1 C12 N20 -173.0(10) . . . . ?
C3 S1 C5 N2 -1.4(9) . . . . ?
C3 S1 C5 C6 179.6(9) . . . . ?
C3 C1 C2 N2 -178.6(9) 3_656 . . . ?
C3 C1 C2 C3 -0.5(17) 3_656 . . . ?
C3 C1 C12 O13 -169.6(9) 3_656 . . . ?
C3 C1 C12 N20 6.4(17) 3_656 . . . ?
C5 S1 C3 C1 -179.0(11) . . . 3_656 ?
C5 S1 C3 C2 1.7(8) . . . . ?
C5 N2 C2 C1 179.1(9) . . . . ?
C5 N2 C2 C3 0.9(12) . . . . ?
C5 C6 C7 C8 -175.7(11) . . . . ?
C6 C7 C8 C9 172.1(13) . . . . ?
C7 C8 C9 C10 170.8(14) . . . . ?
C8 C9 C10 C11 153.7(17) . . . . ?
C12 O13 C14 C15 -178.8(10) . . . . ?
C12 O13 C14 C19 -1.5(11) . . . . ?
C12 N20 C19 C14 1.1(12) . . . . ?
C12 N20 C19 C18 -178.9(12) . . . . ?
C12 C1 C2 N2 0.9(16) . . . . ?
C12 C1 C2 C3 179.0(10) . . . . ?
C14 O13 C12 N20 2.3(12) . . . . ?
C14 O13 C12 C1 178.7(9) . . . . ?
C14 C15 C16 C17 1.2(17) . . . . ?
C15 C14 C19 N20 177.7(10) . . . . ?
C15 C14 C19 C18 -2.3(18) . . . . ?
C15 C16 C17 C18 -1.9(18) . . . . ?
C16 C17 C18 C19 0.5(17) . . . . ?
C17 C18 C19 N20 -178.6(11) . . . . ?
C17 C18 C19 C14 1.5(17) . . . . ?
C19 N20 C12 O13 -2.1(12) . . . . ?
C19 N20 C12 C1 -178.4(10) . . . . ?
C19 C14 C15 C16 1.0(17) . . . . ?

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