# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1062154'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H36 N4 O2 S2'
_chemical_formula_weight         452.67

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6450(3)
_cell_length_b                   15.1066(4)
_cell_length_c                   13.2140(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.207(2)
_cell_angle_gamma                90.00
_cell_volume                     2520.22(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1731
_cell_measurement_theta_min      2.554
_cell_measurement_theta_max      20.702

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13813
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0810
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         27.54
_reflns_number_total             5782
_reflns_number_gt                3402
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0436P)²+0.4377P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    contr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5782
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.29752(5) 0.06989(5) 0.83171(6) 0.0406(2) Uani 1 1 d . . .
S1A S 0.83164(6) 0.25570(5) 0.78548(5) 0.03623(19) Uani 1 1 d . . .
N2A N 0.66140(15) 0.38608(13) 0.62083(14) 0.0273(5) Uani 1 1 d . . .
N2 N 0.18286(15) 0.16457(13) 0.58372(14) 0.0261(5) Uani 1 1 d . . .
N1A N 0.79690(15) 0.47044(13) 0.65536(15) 0.0297(5) Uani 1 1 d . . .
O1 O 0.12224(14) -0.02219(12) 0.82876(15) 0.0448(5) Uani 1 1 d . . .
C3 C 0.15849(17) 0.17616(16) 0.68099(17) 0.0240(5) Uani 1 1 d . . .
O1A O 0.8587(2) 0.16440(14) 0.62004(15) 0.0667(7) Uani 1 1 d . . .
C4A C 0.83567(19) 0.31774(16) 0.58749(18) 0.0297(6) Uani 1 1 d . . .
H4AA H 0.9066 0.3408 0.5810 0.036 Uiso 1 1 calc R . .
H4AB H 0.8094 0.2980 0.5209 0.036 Uiso 1 1 calc R . .
C3A C 0.76723(18) 0.39055(16) 0.62024(17) 0.0253(5) Uani 1 1 d . . .
C5 C 0.16925(18) 0.04509(16) 0.80357(17) 0.0252(5) Uani 1 1 d . . .
C5A C 0.8426(2) 0.23664(17) 0.65930(19) 0.0326(6) Uani 1 1 d . . .
N1 N 0.19428(15) 0.25623(13) 0.70975(14) 0.0258(5) Uani 1 1 d . . .
C4 C 0.09988(18) 0.11265(16) 0.74137(17) 0.0246(5) Uani 1 1 d . . .
H4A H 0.0511 0.0801 0.6959 0.030 Uiso 1 1 calc R . .
H4B H 0.0580 0.1457 0.7877 0.030 Uiso 1 1 calc R . .
C6 C 0.19222(19) 0.29222(17) 0.81450(17) 0.0286(6) Uani 1 1 d . . .
H6A H 0.1731 0.2439 0.8595 0.034 Uiso 1 1 calc R . .
C2A C 0.6238(2) 0.46489(17) 0.65743(19) 0.0336(6) Uani 1 1 d . . .
H2AA H 0.5532 0.4790 0.6660 0.040 Uiso 1 1 calc R . .
C1 C 0.24154(19) 0.29625(17) 0.62991(18) 0.0310(6) Uani 1 1 d . . .
H1A H 0.2726 0.3521 0.6301 0.037 Uiso 1 1 calc R . .
C9 C 0.1610(2) 0.08413(18) 0.52260(18) 0.0364(7) Uani 1 1 d . . .
H9A H 0.1352 0.0384 0.5676 0.044 Uiso 1 1 calc R . .
C2 C 0.2341(2) 0.23943(17) 0.55215(18) 0.0321(6) Uani 1 1 d . . .
H2A H 0.2592 0.2487 0.4882 0.039 Uiso 1 1 calc R . .
C6A C 0.90486(19) 0.50777(18) 0.66646(19) 0.0334(6) Uani 1 1 d . . .
H6AA H 0.9552 0.4614 0.6499 0.040 Uiso 1 1 calc R . .
C9A C 0.59256(19) 0.31115(17) 0.58905(19) 0.0332(6) Uani 1 1 d . . .
H9AA H 0.6369 0.2642 0.5627 0.040 Uiso 1 1 calc R . .
C8A C 0.9288(2) 0.53553(19) 0.7753(2) 0.0417(7) Uani 1 1 d . . .
H8AA H 0.9225 0.4852 0.8190 0.063 Uiso 1 1 calc R . .
H8AB H 0.8794 0.5804 0.7933 0.063 Uiso 1 1 calc R . .
H8AC H 0.9995 0.5586 0.7827 0.063 Uiso 1 1 calc R . .
C1A C 0.7073(2) 0.51729(18) 0.6782(2) 0.0381(7) Uani 1 1 d . . .
H1AA H 0.7055 0.5747 0.7035 0.046 Uiso 1 1 calc R . .
C11A C 0.5372(2) 0.27492(18) 0.6788(2) 0.0419(7) Uani 1 1 d . . .
H11A H 0.5891 0.2561 0.7301 0.063 Uiso 1 1 calc R . .
H11B H 0.4939 0.2254 0.6574 0.063 Uiso 1 1 calc R . .
H11C H 0.4936 0.3202 0.7057 0.063 Uiso 1 1 calc R . .
C8 C 0.3014(2) 0.32477(18) 0.84937(18) 0.0364(7) Uani 1 1 d . . .
H8A H 0.3515 0.2773 0.8454 0.055 Uiso 1 1 calc R . .
H8B H 0.3005 0.3451 0.9182 0.055 Uiso 1 1 calc R . .
H8C H 0.3216 0.3726 0.8067 0.055 Uiso 1 1 calc R . .
C7 C 0.1081(2) 0.36317(18) 0.8184(2) 0.0430(7) Uani 1 1 d . . .
H7A H 0.0405 0.3388 0.7966 0.065 Uiso 1 1 calc R . .
H7B H 0.1250 0.4111 0.7745 0.065 Uiso 1 1 calc R . .
H7C H 0.1054 0.3846 0.8866 0.065 Uiso 1 1 calc R . .
C10A C 0.5151(2) 0.3414(2) 0.50458(19) 0.0467(8) Uani 1 1 d . . .
H10A H 0.5535 0.3634 0.4492 0.070 Uiso 1 1 calc R . .
H10B H 0.4711 0.3876 0.5291 0.070 Uiso 1 1 calc R . .
H10C H 0.4716 0.2924 0.4819 0.070 Uiso 1 1 calc R . .
C7A C 0.9142(2) 0.5830(2) 0.5911(2) 0.0511(8) Uani 1 1 d . . .
H7AA H 0.8987 0.5612 0.5236 0.077 Uiso 1 1 calc R . .
H7AB H 0.9849 0.6063 0.5963 0.077 Uiso 1 1 calc R . .
H7AC H 0.8649 0.6289 0.6057 0.077 Uiso 1 1 calc R . .
C11 C 0.2612(3) 0.0505(2) 0.4797(2) 0.0591(9) Uani 1 1 d . . .
H11D H 0.3130 0.0389 0.5340 0.089 Uiso 1 1 calc R . .
H11E H 0.2882 0.0942 0.4351 0.089 Uiso 1 1 calc R . .
H11F H 0.2464 -0.0032 0.4426 0.089 Uiso 1 1 calc R . .
C10 C 0.0743(3) 0.1029(2) 0.4419(2) 0.0659(10) Uani 1 1 d . . .
H10D H 0.0123 0.1235 0.4734 0.099 Uiso 1 1 calc R . .
H10E H 0.0578 0.0497 0.4047 0.099 Uiso 1 1 calc R . .
H10F H 0.0979 0.1475 0.3966 0.099 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 C5 1.686(2) . ?
S1A C5A 1.705(3) . ?
N2A C3A 1.340(3) . ?
N2A C2A 1.380(3) . ?
N2A C9A 1.475(3) . ?
N2 C3 1.350(3) . ?
N2 C2 1.380(3) . ?
N2 C9 1.476(3) . ?
N1A C3A 1.339(3) . ?
N1A C1A 1.384(3) . ?
N1A C6A 1.477(3) . ?
O1 C5 1.233(3) . ?
C3 N1 1.339(3) . ?
C3 C4 1.474(3) . ?
O1A C5A 1.230(3) . ?
C4A C3A 1.479(3) . ?
C4A C5A 1.549(3) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C5 C4 1.551(3) . ?
N1 C1 1.381(3) . ?
N1 C6 1.489(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C7 1.513(3) . ?
C6 C8 1.513(3) . ?
C6 H6A 0.9800 . ?
C2A C1A 1.336(3) . ?
C2A H2AA 0.9300 . ?
C1 C2 1.338(3) . ?
C1 H1A 0.9300 . ?
C9 C11 1.505(4) . ?
C9 C10 1.513(4) . ?
C9 H9A 0.9800 . ?
C2 H2A 0.9300 . ?
C6A C8A 1.512(3) . ?
C6A C7A 1.520(3) . ?
C6A H6AA 0.9800 . ?
C9A C11A 1.512(3) . ?
C9A C10A 1.514(3) . ?
C9A H9AA 0.9800 . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C1A H1AA 0.9300 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 0.9600 . ?
C11 H11D 0.9600 . ?
C11 H11E 0.9600 . ?
C11 H11F 0.9600 . ?
C10 H10D 0.9600 . ?
C10 H10E 0.9600 . ?
C10 H10F 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
C3A N2A C2A 108.8(2) . . ?
C3A N2A C9A 127.6(2) . . ?
C2A N2A C9A 123.5(2) . . ?
C3 N2 C2 108.5(2) . . ?
C3 N2 C9 125.6(2) . . ?
C2 N2 C9 125.86(19) . . ?
C3A N1A C1A 108.6(2) . . ?
C3A N1A C6A 128.2(2) . . ?
C1A N1A C6A 123.1(2) . . ?
N1 C3 N2 107.2(2) . . ?
N1 C3 C4 127.3(2) . . ?
N2 C3 C4 125.4(2) . . ?
C3A C4A C5A 115.01(19) . . ?
C3A C4A H4AA 108.5 . . ?
C5A C4A H4AA 108.5 . . ?
C3A C4A H4AB 108.5 . . ?
C5A C4A H4AB 108.5 . . ?
H4AA C4A H4AB 107.5 . . ?
N1A C3A N2A 107.7(2) . . ?
N1A C3A C4A 127.9(2) . . ?
N2A C3A C4A 124.4(2) . . ?
O1 C5 C4 114.7(2) . . ?
O1 C5 S1 126.6(2) . . ?
C4 C5 S1 118.63(17) . . ?
O1A C5A C4A 116.6(2) . . ?
O1A C5A S1A 125.9(2) . . ?
C4A C5A S1A 117.43(18) . . ?
C3 N1 C1 109.42(19) . . ?
C3 N1 C6 124.79(19) . . ?
C1 N1 C6 125.6(2) . . ?
C3 C4 C5 115.37(19) . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
C5 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
N1 C6 C7 109.8(2) . . ?
N1 C6 C8 109.80(19) . . ?
C7 C6 C8 113.0(2) . . ?
N1 C6 H6A 108.0 . . ?
C7 C6 H6A 108.0 . . ?
C8 C6 H6A 108.0 . . ?
C1A C2A N2A 107.4(2) . . ?
C1A C2A H2AA 126.3 . . ?
N2A C2A H2AA 126.3 . . ?
C2 C1 N1 106.9(2) . . ?
C2 C1 H1A 126.5 . . ?
N1 C1 H1A 126.5 . . ?
N2 C9 C11 110.4(2) . . ?
N2 C9 C10 109.7(2) . . ?
C11 C9 C10 113.0(2) . . ?
N2 C9 H9A 107.9 . . ?
C11 C9 H9A 107.9 . . ?
C10 C9 H9A 107.9 . . ?
C1 C2 N2 107.9(2) . . ?
C1 C2 H2A 126.0 . . ?
N2 C2 H2A 126.0 . . ?
N1A C6A C8A 109.6(2) . . ?
N1A C6A C7A 109.0(2) . . ?
C8A C6A C7A 113.4(2) . . ?
N1A C6A H6AA 108.2 . . ?
C8A C6A H6AA 108.2 . . ?
C7A C6A H6AA 108.2 . . ?
N2A C9A C11A 110.2(2) . . ?
N2A C9A C10A 109.0(2) . . ?
C11A C9A C10A 112.3(2) . . ?
N2A C9A H9AA 108.4 . . ?
C11A C9A H9AA 108.4 . . ?
C10A C9A H9AA 108.4 . . ?
C6A C8A H8AA 109.5 . . ?
C6A C8A H8AB 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
C6A C8A H8AC 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C2A C1A N1A 107.4(2) . . ?
C2A C1A H1AA 126.3 . . ?
N1A C1A H1AA 126.3 . . ?
C9A C11A H11A 109.5 . . ?
C9A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C9A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C6A C7A H7AA 109.5 . . ?
C6A C7A H7AB 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
C6A C7A H7AC 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C9 C11 H11D 109.5 . . ?
C9 C11 H11E 109.5 . . ?
H11D C11 H11E 109.5 . . ?
C9 C11 H11F 109.5 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 109.5 . . ?
C9 C10 H10D 109.5 . . ?
C9 C10 H10E 109.5 . . ?
H10D C10 H10E 109.5 . . ?
C9 C10 H10F 109.5 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1062155'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 N2 O S'
_chemical_formula_weight         344.50

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4317(3)
_cell_length_b                   15.4783(5)
_cell_length_c                   11.9638(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.189(2)
_cell_angle_gamma                90.00
_cell_volume                     1888.19(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1487
_cell_measurement_theta_min      2.392
_cell_measurement_theta_max      23.506

_exptl_crystal_description       block
_exptl_crystal_colour            yellowish
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10264
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4321
_reflns_number_gt                2737
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0557P)²+0.0234P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    contr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4321
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.48285(6) 0.00063(4) 0.23144(5) 0.03640(18) Uani 1 1 d . . .
N2 N 0.77386(15) 0.16393(11) 0.30169(14) 0.0211(4) Uani 1 1 d . . .
N1 N 0.58461(15) 0.20497(11) 0.32804(14) 0.0219(4) Uani 1 1 d . . .
C3 C 0.67272(18) 0.14081(13) 0.34983(17) 0.0215(4) Uani 1 1 d . . .
C10 C 1.00178(19) 0.12704(14) 0.38748(19) 0.0261(5) Uani 1 1 d . . .
C9 C 0.89288(18) 0.11543(13) 0.29893(18) 0.0235(5) Uani 1 1 d . . .
C4 C 0.6667(2) 0.06269(13) 0.41931(18) 0.0260(5) Uani 1 1 d . . .
H4A H 0.6354 0.0799 0.4868 0.031 Uiso 1 1 calc R . .
H4B H 0.7555 0.0414 0.4451 0.031 Uiso 1 1 calc R . .
O1 O 0.58883(17) -0.08040(11) 0.42073(16) 0.0464(5) Uani 1 1 d . . .
C14 C 0.89371(19) 0.06579(14) 0.20118(18) 0.0260(5) Uani 1 1 d . . .
C11 C 1.1190(2) 0.08800(14) 0.3750(2) 0.0317(5) Uani 1 1 d . . .
H11A H 1.1939 0.0943 0.4323 0.038 Uiso 1 1 calc R . .
C5 C 0.5798(2) -0.01453(15) 0.3624(2) 0.0300(5) Uani 1 1 d . . .
C12 C 1.1250(2) 0.04016(15) 0.2787(2) 0.0347(6) Uani 1 1 d . . .
H12A H 1.2040 0.0155 0.2711 0.042 Uiso 1 1 calc R . .
C6 C 0.45731(19) 0.20901(15) 0.36565(18) 0.0273(5) Uani 1 1 d . . .
H6A H 0.4397 0.1521 0.3951 0.033 Uiso 1 1 calc R . .
C2 C 0.74760(19) 0.24301(13) 0.24939(18) 0.0247(5) Uani 1 1 d . . .
H2A H 0.8015 0.2731 0.2101 0.030 Uiso 1 1 calc R . .
C1 C 0.62962(19) 0.26897(14) 0.26548(17) 0.0248(5) Uani 1 1 d . . .
H1A H 0.5867 0.3201 0.2395 0.030 Uiso 1 1 calc R . .
C15 C 0.7740(2) 0.05407(14) 0.10545(18) 0.0282(5) Uani 1 1 d . . .
H15A H 0.6971 0.0732 0.1337 0.034 Uiso 1 1 calc R . .
C8 C 0.3490(2) 0.22985(16) 0.2636(2) 0.0360(6) Uani 1 1 d . . .
H8A H 0.3457 0.1860 0.2064 0.054 Uiso 1 1 calc R . .
H8B H 0.3661 0.2848 0.2326 0.054 Uiso 1 1 calc R . .
H8C H 0.2666 0.2320 0.2871 0.054 Uiso 1 1 calc R . .
C13 C 1.0138(2) 0.02885(15) 0.1935(2) 0.0329(5) Uani 1 1 d . . .
H13A H 1.0191 -0.0041 0.1297 0.039 Uiso 1 1 calc R . .
C18 C 0.9994(2) 0.18192(14) 0.49191(19) 0.0300(5) Uani 1 1 d . . .
H18A H 0.9078 0.1965 0.4911 0.036 Uiso 1 1 calc R . .
C7 C 0.4693(2) 0.27399(17) 0.4615(2) 0.0371(6) Uani 1 1 d . . .
H7A H 0.5387 0.2569 0.5237 0.056 Uiso 1 1 calc R . .
H7B H 0.3882 0.2765 0.4872 0.056 Uiso 1 1 calc R . .
H7C H 0.4885 0.3299 0.4344 0.056 Uiso 1 1 calc R . .
C17 C 0.7834(2) 0.10965(16) 0.00224(19) 0.0360(6) Uani 1 1 d . . .
H17A H 0.7955 0.1690 0.0254 0.054 Uiso 1 1 calc R . .
H17B H 0.7042 0.1040 -0.0550 0.054 Uiso 1 1 calc R . .
H17C H 0.8566 0.0909 -0.0286 0.054 Uiso 1 1 calc R . .
C20 C 1.0741(2) 0.26617(16) 0.4873(2) 0.0430(6) Uani 1 1 d . . .
H20A H 1.0387 0.2957 0.4170 0.064 Uiso 1 1 calc R . .
H20B H 1.1651 0.2537 0.4913 0.064 Uiso 1 1 calc R . .
H20C H 1.0655 0.3021 0.5507 0.064 Uiso 1 1 calc R . .
C16 C 0.7526(3) -0.04049(16) 0.0688(2) 0.0435(6) Uani 1 1 d . . .
H16A H 0.7459 -0.0751 0.1339 0.065 Uiso 1 1 calc R . .
H16B H 0.8253 -0.0601 0.0380 0.065 Uiso 1 1 calc R . .
H16C H 0.6732 -0.0455 0.0116 0.065 Uiso 1 1 calc R . .
C19 C 1.0545(3) 0.13389(17) 0.6036(2) 0.0469(7) Uani 1 1 d . . .
H19A H 1.0059 0.0815 0.6061 0.070 Uiso 1 1 calc R . .
H19B H 1.0472 0.1699 0.6673 0.070 Uiso 1 1 calc R . .
H19C H 1.1451 0.1202 0.6075 0.070 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 C5 1.692(2) . ?
N2 C3 1.353(2) . ?
N2 C2 1.376(3) . ?
N2 C9 1.457(2) . ?
N1 C3 1.341(2) . ?
N1 C1 1.382(2) . ?
N1 C6 1.491(2) . ?
C3 C4 1.476(3) . ?
C10 C9 1.392(3) . ?
C10 C11 1.400(3) . ?
C10 C18 1.515(3) . ?
C9 C14 1.401(3) . ?
C4 C5 1.566(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O1 C5 1.228(3) . ?
C14 C13 1.398(3) . ?
C14 C15 1.516(3) . ?
C11 C12 1.382(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.383(3) . ?
C12 H12A 0.9300 . ?
C6 C7 1.510(3) . ?
C6 C8 1.513(3) . ?
C6 H6A 0.9800 . ?
C2 C1 1.347(3) . ?
C2 H2A 0.9300 . ?
C1 H1A 0.9300 . ?
C15 C17 1.525(3) . ?
C15 C16 1.531(3) . ?
C15 H15A 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C13 H13A 0.9300 . ?
C18 C20 1.526(3) . ?
C18 C19 1.531(3) . ?
C18 H18A 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C3 N2 C2 109.31(16) . . ?
C3 N2 C9 128.20(17) . . ?
C2 N2 C9 122.47(15) . . ?
C3 N1 C1 109.80(16) . . ?
C3 N1 C6 126.17(16) . . ?
C1 N1 C6 124.03(17) . . ?
N1 C3 N2 106.60(17) . . ?
N1 C3 C4 127.38(16) . . ?
N2 C3 C4 125.89(17) . . ?
C9 C10 C11 116.99(19) . . ?
C9 C10 C18 123.18(18) . . ?
C11 C10 C18 119.79(19) . . ?
C10 C9 C14 123.95(18) . . ?
C10 C9 N2 118.59(18) . . ?
C14 C9 N2 117.19(18) . . ?
C3 C4 C5 118.02(18) . . ?
C3 C4 H4A 107.8 . . ?
C5 C4 H4A 107.8 . . ?
C3 C4 H4B 107.8 . . ?
C5 C4 H4B 107.8 . . ?
H4A C4 H4B 107.1 . . ?
C13 C14 C9 116.3(2) . . ?
C13 C14 C15 120.54(19) . . ?
C9 C14 C15 123.16(17) . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
O1 C5 C4 114.7(2) . . ?
O1 C5 S1 126.91(18) . . ?
C4 C5 S1 118.33(16) . . ?
C11 C12 C13 120.21(19) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
N1 C6 C7 108.73(17) . . ?
N1 C6 C8 109.04(16) . . ?
C7 C6 C8 113.48(19) . . ?
N1 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C8 C6 H6A 108.5 . . ?
C1 C2 N2 107.50(17) . . ?
C1 C2 H2A 126.3 . . ?
N2 C2 H2A 126.3 . . ?
C2 C1 N1 106.79(18) . . ?
C2 C1 H1A 126.6 . . ?
N1 C1 H1A 126.6 . . ?
C14 C15 C17 111.14(17) . . ?
C14 C15 C16 112.19(19) . . ?
C17 C15 C16 109.76(19) . . ?
C14 C15 H15A 107.9 . . ?
C17 C15 H15A 107.9 . . ?
C16 C15 H15A 107.9 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C13 C14 121.6(2) . . ?
C12 C13 H13A 119.2 . . ?
C14 C13 H13A 119.2 . . ?
C10 C18 C20 110.60(18) . . ?
C10 C18 C19 112.27(19) . . ?
C20 C18 C19 110.2(2) . . ?
C10 C18 H18A 107.9 . . ?
C20 C18 H18A 107.9 . . ?
C19 C18 H18A 107.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1062156'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H18 N2 S2'
_chemical_formula_weight         242.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9953(12)
_cell_length_b                   15.115(2)
_cell_length_c                   11.4875(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.186(5)
_cell_angle_gamma                90.00
_cell_volume                     1326.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2702
_cell_measurement_theta_min      2.294
_cell_measurement_theta_max      25.048

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8599
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         29.39
_reflns_number_total             3638
_reflns_number_gt                2486
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.3001P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    contr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3638
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.21769(8) 0.18308(4) 0.83904(5) 0.0732(2) Uani 1 1 d . . .
S2 S -0.10464(7) 0.08193(4) 0.71854(7) 0.0780(2) Uani 1 1 d . . .
C3 C 0.1256(2) 0.28774(11) 0.60222(14) 0.0421(4) Uani 1 1 d . . .
C5 C 0.0366(2) 0.16423(11) 0.72586(15) 0.0453(4) Uani 1 1 d . . .
N1 N 0.16297(19) 0.36911(9) 0.64776(13) 0.0467(3) Uani 1 1 d . . .
N2 N 0.23090(18) 0.27080(9) 0.53331(12) 0.0456(3) Uani 1 1 d . . .
C4 C -0.0138(2) 0.22876(12) 0.61841(15) 0.0459(4) Uani 1 1 d . . .
H4A H -0.0590 0.1946 0.5443 0.055 Uiso 1 1 calc R . .
H4B H -0.1088 0.2655 0.6272 0.055 Uiso 1 1 calc R . .
C2 C 0.3343(2) 0.34367(12) 0.53431(16) 0.0516(4) Uani 1 1 d . . .
H2A H 0.4177 0.3495 0.4929 0.062 Uiso 1 1 calc R . .
C9 C 0.2401(3) 0.18650(12) 0.46939(18) 0.0552(5) Uani 1 1 d . . .
H9A H 0.1659 0.1430 0.4937 0.066 Uiso 1 1 calc R . .
C1 C 0.2931(2) 0.40478(12) 0.60576(17) 0.0525(4) Uani 1 1 d . . .
H1A H 0.3428 0.4607 0.6236 0.063 Uiso 1 1 calc R . .
C6 C 0.0812(3) 0.41341(13) 0.73160(19) 0.0590(5) Uani 1 1 d . . .
H6A H 0.0181 0.3685 0.7636 0.071 Uiso 1 1 calc R . .
C8 C 0.2213(3) 0.45235(16) 0.8378(2) 0.0769(7) Uani 1 1 d . . .
H8A H 0.2995 0.4064 0.8786 0.115 Uiso 1 1 calc R . .
H8B H 0.1677 0.4791 0.8937 0.115 Uiso 1 1 calc R . .
H8C H 0.2856 0.4963 0.8085 0.115 Uiso 1 1 calc R . .
C11 C 0.1694(3) 0.19988(18) 0.3328(2) 0.0780(7) Uani 1 1 d . . .
H11A H 0.0511 0.2211 0.3126 0.117 Uiso 1 1 calc R . .
H11B H 0.1718 0.1446 0.2920 0.117 Uiso 1 1 calc R . .
H11C H 0.2405 0.2424 0.3071 0.117 Uiso 1 1 calc R . .
C10 C 0.4261(3) 0.15255(16) 0.5086(2) 0.0802(7) Uani 1 1 d . . .
H10A H 0.4643 0.1450 0.5954 0.120 Uiso 1 1 calc R . .
H10B H 0.5009 0.1943 0.4854 0.120 Uiso 1 1 calc R . .
H10C H 0.4312 0.0968 0.4698 0.120 Uiso 1 1 calc R . .
C7 C -0.0506(4) 0.48022(19) 0.6616(3) 0.0934(8) Uani 1 1 d . . .
H7A H -0.1358 0.4511 0.5961 0.140 Uiso 1 1 calc R . .
H7B H 0.0082 0.5250 0.6291 0.140 Uiso 1 1 calc R . .
H7C H -0.1081 0.5071 0.7152 0.140 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 C5 1.6598(19) . ?
S2 C5 1.6656(18) . ?
C3 N1 1.335(2) . ?
C3 N2 1.340(2) . ?
C3 C4 1.481(2) . ?
C5 C4 1.531(2) . ?
N1 C1 1.379(2) . ?
N1 C6 1.475(2) . ?
N2 C2 1.375(2) . ?
N2 C9 1.483(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2 C1 1.340(3) . ?
C2 H2A 0.9300 . ?
C9 C10 1.510(3) . ?
C9 C11 1.516(3) . ?
C9 H9A 0.9800 . ?
C1 H1A 0.9300 . ?
C6 C7 1.508(3) . ?
C6 C8 1.510(3) . ?
C6 H6A 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
N1 C3 N2 107.48(14) . . ?
N1 C3 C4 126.50(15) . . ?
N2 C3 C4 125.93(15) . . ?
C4 C5 S1 118.90(12) . . ?
C4 C5 S2 114.96(12) . . ?
S1 C5 S2 126.11(11) . . ?
C3 N1 C1 109.13(14) . . ?
C3 N1 C6 125.64(15) . . ?
C1 N1 C6 125.22(15) . . ?
C3 N2 C2 108.87(14) . . ?
C3 N2 C9 126.03(15) . . ?
C2 N2 C9 125.06(14) . . ?
C3 C4 C5 117.12(13) . . ?
C3 C4 H4A 108.0 . . ?
C5 C4 H4A 108.0 . . ?
C3 C4 H4B 108.0 . . ?
C5 C4 H4B 108.0 . . ?
H4A C4 H4B 107.3 . . ?
C1 C2 N2 107.51(16) . . ?
C1 C2 H2A 126.2 . . ?
N2 C2 H2A 126.2 . . ?
N2 C9 C10 109.43(17) . . ?
N2 C9 C11 109.87(17) . . ?
C10 C9 C11 112.77(19) . . ?
N2 C9 H9A 108.2 . . ?
C10 C9 H9A 108.2 . . ?
C11 C9 H9A 108.2 . . ?
C2 C1 N1 107.00(16) . . ?
C2 C1 H1A 126.5 . . ?
N1 C1 H1A 126.5 . . ?
N1 C6 C7 109.31(18) . . ?
N1 C6 C8 109.77(17) . . ?
C7 C6 C8 113.8(2) . . ?
N1 C6 H6A 107.9 . . ?
C7 C6 H6A 107.9 . . ?
C8 C6 H6A 107.9 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.39
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1062157'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 N2 S2'
_chemical_formula_weight         360.56

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1668(11)
_cell_length_b                   16.0775(16)
_cell_length_c                   12.9862(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.802(5)
_cell_angle_gamma                90.00
_cell_volume                     2061.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2303
_cell_measurement_theta_min      2.421
_cell_measurement_theta_max      22.85

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10410
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         27.66
_reflns_number_total             4733
_reflns_number_gt                3210
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0499P)²+0.3373P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    contr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4733
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.96711(6) 0.08416(3) 0.10203(4) 0.05655(17) Uani 1 1 d . . .
S2 S 1.02088(6) -0.02228(4) 0.29517(4) 0.0678(2) Uani 1 1 d . . .
N2 N 0.71185(14) -0.15983(9) 0.20318(11) 0.0378(3) Uani 1 1 d . . .
N1 N 0.89870(14) -0.20525(10) 0.17314(12) 0.0422(4) Uani 1 1 d . . .
C4 C 0.83295(17) -0.05966(11) 0.10891(14) 0.0377(4) Uani 1 1 d . . .
H4A H 0.7466 -0.0309 0.0934 0.045 Uiso 1 1 calc R . .
H4B H 0.8544 -0.0721 0.0417 0.045 Uiso 1 1 calc R . .
C3 C 0.81643(16) -0.13925(11) 0.16141(13) 0.0361(4) Uani 1 1 d . . .
C10 C 0.48165(18) -0.12292(12) 0.10997(15) 0.0443(4) Uani 1 1 d . . .
C9 C 0.58929(17) -0.11207(11) 0.19887(14) 0.0404(4) Uani 1 1 d . . .
C2 C 0.73088(19) -0.23980(12) 0.24224(15) 0.0477(5) Uani 1 1 d . . .
H2A H 0.6735 -0.2688 0.2755 0.057 Uiso 1 1 calc R . .
C5 C 0.94139(17) 0.00021(12) 0.17058(14) 0.0412(4) Uani 1 1 d . . .
C1 C 0.84655(19) -0.26818(13) 0.22367(16) 0.0506(5) Uani 1 1 d . . .
H1A H 0.8846 -0.3204 0.2414 0.061 Uiso 1 1 calc R . .
C14 C 0.58212(19) -0.06257(12) 0.28561(15) 0.0469(5) Uani 1 1 d . . .
C6 C 1.02582(19) -0.21242(13) 0.13599(16) 0.0510(5) Uani 1 1 d . . .
H6A H 1.0454 -0.1580 0.1091 0.061 Uiso 1 1 calc R . .
C11 C 0.36096(19) -0.08204(13) 0.11081(18) 0.0540(5) Uani 1 1 d . . .
H11A H 0.2870 -0.0877 0.0532 0.065 Uiso 1 1 calc R . .
C18 C 0.4898(2) -0.17817(13) 0.01720(16) 0.0510(5) Uani 1 1 d . . .
H18A H 0.5829 -0.1989 0.0292 0.061 Uiso 1 1 calc R . .
C15 C 0.6998(2) -0.05231(13) 0.38188(16) 0.0533(5) Uani 1 1 d . . .
H15A H 0.7802 -0.0770 0.3649 0.064 Uiso 1 1 calc R . .
C12 C 0.3495(2) -0.03356(14) 0.19539(19) 0.0614(6) Uani 1 1 d . . .
H12A H 0.2679 -0.0072 0.1948 0.074 Uiso 1 1 calc R . .
C7 C 1.0034(3) -0.27424(16) 0.0449(2) 0.0760(7) Uani 1 1 d . . .
H7A H 0.9297 -0.2557 -0.0113 0.114 Uiso 1 1 calc R . .
H7B H 0.9821 -0.3278 0.0693 0.114 Uiso 1 1 calc R . .
H7C H 1.0842 -0.2783 0.0191 0.114 Uiso 1 1 calc R . .
C13 C 0.4579(2) -0.02382(14) 0.28063(18) 0.0602(6) Uani 1 1 d . . .
H13A H 0.4483 0.0096 0.3368 0.072 Uiso 1 1 calc R . .
C8 C 1.1421(2) -0.23525(18) 0.2285(2) 0.0793(8) Uani 1 1 d . . .
H8A H 1.1516 -0.1935 0.2825 0.119 Uiso 1 1 calc R . .
H8B H 1.2244 -0.2387 0.2046 0.119 Uiso 1 1 calc R . .
H8C H 1.1241 -0.2880 0.2568 0.119 Uiso 1 1 calc R . .
C17 C 0.6730(3) -0.09865(18) 0.47760(19) 0.0791(8) Uani 1 1 d . . .
H17A H 0.6551 -0.1562 0.4598 0.119 Uiso 1 1 calc R . .
H17B H 0.5961 -0.0746 0.4972 0.119 Uiso 1 1 calc R . .
H17C H 0.7510 -0.0943 0.5360 0.119 Uiso 1 1 calc R . .
C19 C 0.3964(3) -0.25275(17) 0.0101(2) 0.0856(8) Uani 1 1 d . . .
H19A H 0.4182 -0.2827 0.0760 0.128 Uiso 1 1 calc R . .
H19B H 0.4077 -0.2886 -0.0462 0.128 Uiso 1 1 calc R . .
H19C H 0.3041 -0.2341 -0.0038 0.128 Uiso 1 1 calc R . .
C16 C 0.7304(3) 0.03896(17) 0.4092(2) 0.0915(9) Uani 1 1 d . . .
H16A H 0.7479 0.0672 0.3487 0.137 Uiso 1 1 calc R . .
H16B H 0.8086 0.0430 0.4675 0.137 Uiso 1 1 calc R . .
H16C H 0.6541 0.0641 0.4285 0.137 Uiso 1 1 calc R . .
C20 C 0.4570(3) -0.13135(18) -0.0876(2) 0.0859(8) Uani 1 1 d . . .
H20A H 0.5177 -0.0850 -0.0835 0.129 Uiso 1 1 calc R . .
H20B H 0.3654 -0.1115 -0.1019 0.129 Uiso 1 1 calc R . .
H20C H 0.4674 -0.1680 -0.1435 0.129 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 C5 1.6714(19) . ?
S2 C5 1.6666(19) . ?
N2 C3 1.345(2) . ?
N2 C2 1.379(2) . ?
N2 C9 1.453(2) . ?
N1 C3 1.337(2) . ?
N1 C1 1.379(2) . ?
N1 C6 1.488(2) . ?
C4 C3 1.478(2) . ?
C4 C5 1.537(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C10 C11 1.394(3) . ?
C10 C9 1.399(2) . ?
C10 C18 1.515(3) . ?
C9 C14 1.395(3) . ?
C2 C1 1.336(3) . ?
C2 H2A 0.9300 . ?
C1 H1A 0.9300 . ?
C14 C13 1.396(3) . ?
C14 C15 1.519(3) . ?
C6 C8 1.516(3) . ?
C6 C7 1.520(3) . ?
C6 H6A 0.9800 . ?
C11 C12 1.374(3) . ?
C11 H11A 0.9300 . ?
C18 C19 1.519(3) . ?
C18 C20 1.521(3) . ?
C18 H18A 0.9800 . ?
C15 C16 1.524(3) . ?
C15 C17 1.528(3) . ?
C15 H15A 0.9800 . ?
C12 C13 1.372(3) . ?
C12 H12A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C3 N2 C2 108.82(14) . . ?
C3 N2 C9 127.41(14) . . ?
C2 N2 C9 123.41(14) . . ?
C3 N1 C1 109.60(15) . . ?
C3 N1 C6 126.34(15) . . ?
C1 N1 C6 124.04(16) . . ?
C3 C4 C5 116.62(14) . . ?
C3 C4 H4A 108.1 . . ?
C5 C4 H4A 108.1 . . ?
C3 C4 H4B 108.1 . . ?
C5 C4 H4B 108.1 . . ?
H4A C4 H4B 107.3 . . ?
N1 C3 N2 106.98(15) . . ?
N1 C3 C4 127.06(15) . . ?
N2 C3 C4 125.92(15) . . ?
C11 C10 C9 116.83(18) . . ?
C11 C10 C18 119.86(17) . . ?
C9 C10 C18 123.28(16) . . ?
C14 C9 C10 123.78(16) . . ?
C14 C9 N2 118.67(16) . . ?
C10 C9 N2 117.42(16) . . ?
C1 C2 N2 107.72(16) . . ?
C1 C2 H2A 126.1 . . ?
N2 C2 H2A 126.1 . . ?
C4 C5 S2 119.43(13) . . ?
C4 C5 S1 114.34(13) . . ?
S2 C5 S1 126.23(11) . . ?
C2 C1 N1 106.88(17) . . ?
C2 C1 H1A 126.6 . . ?
N1 C1 H1A 126.6 . . ?
C9 C14 C13 115.98(19) . . ?
C9 C14 C15 122.94(17) . . ?
C13 C14 C15 121.06(18) . . ?
N1 C6 C8 109.61(16) . . ?
N1 C6 C7 108.80(17) . . ?
C8 C6 C7 113.7(2) . . ?
N1 C6 H6A 108.2 . . ?
C8 C6 H6A 108.2 . . ?
C7 C6 H6A 108.2 . . ?
C12 C11 C10 121.08(19) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C10 C18 C19 111.04(18) . . ?
C10 C18 C20 112.30(18) . . ?
C19 C18 C20 109.7(2) . . ?
C10 C18 H18A 107.9 . . ?
C19 C18 H18A 107.9 . . ?
C20 C18 H18A 107.9 . . ?
C14 C15 C16 111.89(19) . . ?
C14 C15 C17 111.00(18) . . ?
C16 C15 C17 110.3(2) . . ?
C14 C15 H15A 107.8 . . ?
C16 C15 H15A 107.8 . . ?
C17 C15 H15A 107.8 . . ?
C13 C12 C11 120.30(19) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C13 C14 122.0(2) . . ?
C12 C13 H13A 119.0 . . ?
C14 C13 H13A 119.0 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.66
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.038

