# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1403546'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2,4,6-tris(phenylthio)-1,3,5-triazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 N3 S3'
_chemical_formula_sum            'C21 H15 N3 S3'
_chemical_formula_weight         405.54

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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                   33.368(9)
_cell_length_b                   13.694(3)
_cell_length_c                   23.569(7)
_cell_angle_alpha                90
_cell_angle_beta                 133.022(10)
_cell_angle_gamma                90
_cell_volume                     7873(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2589
_cell_measurement_theta_min      2.364
_cell_measurement_theta_max      20.815
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             3360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.387
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.369
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20642
_diffrn_reflns_av_unetI/netI     0.0759
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.705
_diffrn_reflns_theta_max         25.260
_diffrn_reflns_theta_full        25.260
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7104
_reflns_number_gt                4807
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;

_computing_data_collection       'Bruker Apex 2'
_computing_cell_refinement       'Bruker Apex 2'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'Sir92 (Altomare et al. 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7104
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.58079(3) 0.52268(6) 0.21879(5) 0.0335(2) Uani 1 1 d . . . . .
S2A S 0.75225(3) 0.75691(6) 0.39998(5) 0.0362(2) Uani 1 1 d . . . . .
S3A S 0.78546(4) 0.40606(7) 0.36590(6) 0.0465(3) Uani 1 1 d . . . . .
N1A N 0.68320(10) 0.46676(18) 0.29191(14) 0.0288(6) Uani 1 1 d . . . . .
N2A N 0.66730(10) 0.63161(18) 0.30699(14) 0.0287(6) Uani 1 1 d . . . . .
N3A N 0.75821(11) 0.57631(18) 0.37540(15) 0.0337(7) Uani 1 1 d . . . . .
C1A C 0.65138(13) 0.5399(2) 0.27877(16) 0.0274(7) Uani 1 1 d . . . . .
C2A C 0.72118(14) 0.6437(2) 0.35484(18) 0.0310(7) Uani 1 1 d . . . . .
C3A C 0.73617(13) 0.4904(2) 0.34077(17) 0.0313(7) Uani 1 1 d . . . . .
C4A C 0.57151(12) 0.3968(2) 0.19538(17) 0.0278(7) Uani 1 1 d . . . . .
C5A C 0.55010(12) 0.3375(2) 0.21702(17) 0.0360(8) Uani 1 1 d . . . . .
H5AA H 0.5430 0.3632 0.2469 0.043 Uiso 1 1 calc R U . . .
C6A C 0.53918(13) 0.2398(3) 0.19444(18) 0.0390(8) Uani 1 1 d . . . . .
H6AA H 0.5249 0.1984 0.2095 0.047 Uiso 1 1 calc R U . . .
C7A C 0.54895(13) 0.2028(2) 0.15044(18) 0.0383(8) Uani 1 1 d . . . . .
H7AA H 0.5411 0.1363 0.1347 0.046 Uiso 1 1 calc R U . . .
C8A C 0.57017(13) 0.2629(2) 0.12936(19) 0.0363(8) Uani 1 1 d . . . . .
H8AA H 0.5771 0.2372 0.0993 0.044 Uiso 1 1 calc R U . . .
C9A C 0.58143(12) 0.3591(2) 0.15123(17) 0.0302(7) Uani 1 1 d . . . . .
H9AA H 0.5960 0.3997 0.1363 0.036 Uiso 1 1 calc R U . . .
C10A C 0.69685(14) 0.8387(2) 0.35722(19) 0.0338(8) Uani 1 1 d . . . . .
C11A C 0.69062(16) 0.8819(2) 0.4039(2) 0.0438(9) Uani 1 1 d . . . . .
H11A H 0.7131 0.8624 0.4565 0.053 Uiso 1 1 calc R U . . .
C12A C 0.65147(19) 0.9534(3) 0.3735(3) 0.0595(11) Uani 1 1 d . . . . .
H12A H 0.6476 0.9841 0.4057 0.071 Uiso 1 1 calc R U . . .
C13A C 0.61802(17) 0.9806(3) 0.2972(2) 0.0536(10) Uani 1 1 d . . . . .
H13A H 0.5910 1.0297 0.2767 0.064 Uiso 1 1 calc R U . . .
C14A C 0.62349(14) 0.9370(2) 0.2504(2) 0.0433(9) Uani 1 1 d . . . . .
H14A H 0.5999 0.9553 0.1974 0.052 Uiso 1 1 calc R U . . .
C15A C 0.66291(14) 0.8668(2) 0.27978(19) 0.0383(8) Uani 1 1 d . . . . .
H15A H 0.6670 0.8376 0.2474 0.046 Uiso 1 1 calc R U . . .
C16A C 0.74783(12) 0.2977(2) 0.31758(18) 0.0322(8) Uani 1 1 d . . . . .
C17A C 0.74232(14) 0.2289(3) 0.35566(19) 0.0374(8) Uani 1 1 d . . . . .
H17A H 0.7567 0.2421 0.4062 0.045 Uiso 1 1 calc R U . . .
C18A C 0.71592(14) 0.1417(3) 0.3196(2) 0.0436(9) Uani 1 1 d . . . . .
H18A H 0.7115 0.0952 0.3449 0.052 Uiso 1 1 calc R U . . .
C19A C 0.69584(13) 0.1220(2) 0.24661(19) 0.0389(8) Uani 1 1 d . . . . .
H19A H 0.6774 0.0621 0.2217 0.047 Uiso 1 1 calc R U . . .
C20A C 0.70230(14) 0.1881(3) 0.21000(19) 0.0403(9) Uani 1 1 d . . . . .
H20A H 0.6885 0.1737 0.1599 0.048 Uiso 1 1 calc R U . . .
C21A C 0.72856(13) 0.2749(3) 0.24502(18) 0.0372(8) Uani 1 1 d . . . . .
H21A H 0.7336 0.3198 0.2196 0.045 Uiso 1 1 calc R U . . .
S1B S 0.89500(4) 0.31449(6) 0.60206(5) 0.0403(2) Uani 1 1 d . . . . .
S2B S 0.93860(4) 0.55838(6) 0.47764(5) 0.0424(2) Uani 1 1 d . . . . .
S3B S 0.90682(4) 0.19952(6) 0.39568(5) 0.0341(2) Uani 1 1 d . . . . .
N1B N 0.89998(10) 0.25996(17) 0.49739(13) 0.0263(6) Uani 1 1 d . . . . .
N2B N 0.92031(10) 0.42475(18) 0.54204(14) 0.0316(6) Uani 1 1 d . . . . .
N3B N 0.92024(10) 0.37625(18) 0.44473(14) 0.0293(6) Uani 1 1 d . . . . .
C1B C 0.90597(12) 0.3328(2) 0.53998(16) 0.0284(7) Uani 1 1 d . . . . .
C2B C 0.92524(12) 0.4419(2) 0.49129(18) 0.0310(7) Uani 1 1 d . . . . .
C3B C 0.90923(12) 0.2860(2) 0.45249(16) 0.0263(7) Uani 1 1 d . . . . .
C4B C 0.86803(14) 0.1945(2) 0.58146(17) 0.0345(8) Uani 1 1 d . . . . .
C5B C 0.81861(16) 0.1855(3) 0.5624(2) 0.0472(10) Uani 1 1 d . . . . .
H5BA H 0.8000 0.2422 0.5573 0.057 Uiso 1 1 calc R U . . .
C6B C 0.79651(18) 0.0940(4) 0.5508(2) 0.0624(12) Uani 1 1 d . . . . .
H6BA H 0.7625 0.0876 0.5373 0.075 Uiso 1 1 calc R U . . .
C7B C 0.8242(2) 0.0121(3) 0.5591(2) 0.0645(13) Uani 1 1 d . . . . .
H7BA H 0.8091 -0.0509 0.5511 0.077 Uiso 1 1 calc R U . . .
C8B C 0.87345(18) 0.0210(3) 0.5787(2) 0.0508(11) Uani 1 1 d . . . . .
H8BA H 0.8923 -0.0358 0.5845 0.061 Uiso 1 1 calc R U . . .
C9B C 0.89553(15) 0.1124(2) 0.59000(18) 0.0395(9) Uani 1 1 d . . . . .
H9BA H 0.9296 0.1184 0.6036 0.047 Uiso 1 1 calc R U . . .
C10B C 0.94375(13) 0.6339(2) 0.54434(18) 0.0346(8) Uani 1 1 d . . . . .
C11B C 0.99398(14) 0.6775(2) 0.6028(2) 0.0389(8) Uani 1 1 d . . . . .
H11B H 1.0245 0.6631 0.6086 0.047 Uiso 1 1 calc R U . . .
C12B C 0.99929(15) 0.7423(3) 0.65251(19) 0.0448(10) Uani 1 1 d . . . . .
H12B H 1.0336 0.7727 0.6928 0.054 Uiso 1 1 calc R U . . .
C13B C 0.95472(15) 0.7630(2) 0.64385(19) 0.0404(9) Uani 1 1 d . . . . .
H13B H 0.9583 0.8079 0.6778 0.048 Uiso 1 1 calc R U . . .
C14B C 0.90512(15) 0.7179(2) 0.58562(19) 0.0403(9) Uani 1 1 d . . . . .
H14B H 0.8748 0.7312 0.5803 0.048 Uiso 1 1 calc R U . . .
C15B C 0.89897(14) 0.6536(2) 0.5349(2) 0.0392(8) Uani 1 1 d . . . . .
H15B H 0.8646 0.6236 0.4943 0.047 Uiso 1 1 calc R U . . .
C16B C 0.89483(13) 0.0895(2) 0.42164(17) 0.0262(7) Uani 1 1 d . . . . .
C17B C 0.93948(14) 0.0348(2) 0.48320(18) 0.0359(8) Uani 1 1 d . . . . .
H17B H 0.9758 0.0581 0.5134 0.043 Uiso 1 1 calc R U . . .
C18B C 0.92970(18) -0.0543(3) 0.4993(2) 0.0496(11) Uani 1 1 d . . . . .
H18B H 0.9596 -0.0931 0.5408 0.060 Uiso 1 1 calc R U . . .
C19B C 0.8767(2) -0.0873(3) 0.4554(3) 0.0532(11) Uani 1 1 d . . . . .
H19B H 0.8703 -0.1494 0.4659 0.064 Uiso 1 1 calc R U . . .
C20B C 0.83335(17) -0.0306(3) 0.3967(2) 0.0444(9) Uani 1 1 d . . . . .
H20B H 0.7969 -0.0523 0.3683 0.053 Uiso 1 1 calc R U . . .
C21B C 0.84214(13) 0.0568(2) 0.37872(18) 0.0325(8) Uani 1 1 d . . . . .
H21B H 0.8120 0.0947 0.3368 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A C1A 1.749(3) . ?
S1A C4A 1.772(3) . ?
S2A C2A 1.761(3) . ?
S2A C10A 1.774(3) . ?
S3A C3A 1.749(3) . ?
S3A C16A 1.767(3) . ?
N1A C3A 1.333(4) . ?
N1A C1A 1.333(4) . ?
N2A C2A 1.329(4) . ?
N2A C1A 1.349(4) . ?
N3A C3A 1.331(4) . ?
N3A C2A 1.341(4) . ?
C4A C5A 1.388(4) . ?
C4A C9A 1.389(4) . ?
C5A C6A 1.394(5) . ?
C5A H5AA 0.9500 . ?
C6A C7A 1.378(5) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.381(5) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.370(4) . ?
C8A H8AA 0.9500 . ?
C9A H9AA 0.9500 . ?
C10A C11A 1.385(4) . ?
C10A C15A 1.393(4) . ?
C11A C12A 1.379(5) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.372(5) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.371(5) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.374(5) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?
C16A C21A 1.391(4) . ?
C16A C17A 1.398(4) . ?
C17A C18A 1.379(5) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.381(4) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.365(5) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.370(5) . ?
C20A H20A 0.9500 . ?
C21A H21A 0.9500 . ?
S1B C1B 1.752(3) . ?
S1B C4B 1.775(3) . ?
S2B C2B 1.745(3) . ?
S2B C10B 1.790(3) . ?
S3B C3B 1.747(3) . ?
S3B C16B 1.771(3) . ?
N1B C1B 1.329(4) . ?
N1B C3B 1.337(4) . ?
N2B C2B 1.335(4) . ?
N2B C1B 1.337(4) . ?
N3B C2B 1.338(4) . ?
N3B C3B 1.337(4) . ?
C4B C9B 1.377(4) . ?
C4B C5B 1.387(5) . ?
C5B C6B 1.384(5) . ?
C5B H5BA 0.9500 . ?
C6B C7B 1.380(6) . ?
C6B H6BA 0.9500 . ?
C7B C8B 1.376(6) . ?
C7B H7BA 0.9500 . ?
C8B C9B 1.382(5) . ?
C8B H8BA 0.9500 . ?
C9B H9BA 0.9500 . ?
C10B C15B 1.378(4) . ?
C10B C11B 1.383(4) . ?
C11B C12B 1.382(5) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.386(5) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.380(5) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.383(4) . ?
C14B H14B 0.9500 . ?
C15B H15B 0.9500 . ?
C16B C21B 1.374(4) . ?
C16B C17B 1.392(4) . ?
C17B C18B 1.382(5) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.379(6) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.371(5) . ?
C19B H19B 0.9500 . ?
C20B C21B 1.366(4) . ?
C20B H20B 0.9500 . ?
C21B H21B 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
C1A S1A C4A 103.64(14) . . ?
C2A S2A C10A 104.88(15) . . ?
C3A S3A C16A 104.20(15) . . ?
C3A N1A C1A 113.2(3) . . ?
C2A N2A C1A 112.6(3) . . ?
C3A N3A C2A 113.6(3) . . ?
N1A C1A N2A 127.0(3) . . ?
N1A C1A S1A 120.4(2) . . ?
N2A C1A S1A 112.6(2) . . ?
N2A C2A N3A 126.9(3) . . ?
N2A C2A S2A 121.4(2) . . ?
N3A C2A S2A 111.7(2) . . ?
N3A C3A N1A 126.6(3) . . ?
N3A C3A S3A 112.2(2) . . ?
N1A C3A S3A 121.2(2) . . ?
C5A C4A C9A 120.2(3) . . ?
C5A C4A S1A 118.6(2) . . ?
C9A C4A S1A 121.0(2) . . ?
C4A C5A C6A 119.2(3) . . ?
C4A C5A H5AA 120.4 . . ?
C6A C5A H5AA 120.4 . . ?
C7A C6A C5A 120.4(3) . . ?
C7A C6A H6AA 119.8 . . ?
C5A C6A H6AA 119.8 . . ?
C6A C7A C8A 119.6(3) . . ?
C6A C7A H7AA 120.2 . . ?
C8A C7A H7AA 120.2 . . ?
C9A C8A C7A 120.9(3) . . ?
C9A C8A H8AA 119.5 . . ?
C7A C8A H8AA 119.5 . . ?
C8A C9A C4A 119.7(3) . . ?
C8A C9A H9AA 120.2 . . ?
C4A C9A H9AA 120.2 . . ?
C11A C10A C15A 119.7(3) . . ?
C11A C10A S2A 118.8(3) . . ?
C15A C10A S2A 121.3(2) . . ?
C12A C11A C10A 119.5(3) . . ?
C12A C11A H11A 120.2 . . ?
C10A C11A H11A 120.2 . . ?
C13A C12A C11A 120.6(4) . . ?
C13A C12A H12A 119.7 . . ?
C11A C12A H12A 119.7 . . ?
C14A C13A C12A 120.1(4) . . ?
C14A C13A H13A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C13A C14A C15A 120.4(4) . . ?
C13A C14A H14A 119.8 . . ?
C15A C14A H14A 119.8 . . ?
C14A C15A C10A 119.7(3) . . ?
C14A C15A H15A 120.1 . . ?
C10A C15A H15A 120.1 . . ?
C21A C16A C17A 119.0(3) . . ?
C21A C16A S3A 120.7(3) . . ?
C17A C16A S3A 120.0(3) . . ?
C18A C17A C16A 119.8(3) . . ?
C18A C17A H17A 120.1 . . ?
C16A C17A H17A 120.1 . . ?
C17A C18A C19A 120.0(3) . . ?
C17A C18A H18A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C20A C19A C18A 120.4(3) . . ?
C20A C19A H19A 119.8 . . ?
C18A C19A H19A 119.8 . . ?
C19A C20A C21A 120.4(3) . . ?
C19A C20A H20A 119.8 . . ?
C21A C20A H20A 119.8 . . ?
C20A C21A C16A 120.3(3) . . ?
C20A C21A H21A 119.8 . . ?
C16A C21A H21A 119.8 . . ?
C1B S1B C4B 105.05(14) . . ?
C2B S2B C10B 104.48(15) . . ?
C3B S3B C16B 102.41(14) . . ?
C1B N1B C3B 113.6(3) . . ?
C2B N2B C1B 113.1(3) . . ?
C2B N3B C3B 113.6(3) . . ?
N1B C1B N2B 126.9(3) . . ?
N1B C1B S1B 120.9(2) . . ?
N2B C1B S1B 112.2(2) . . ?
N2B C2B N3B 126.5(3) . . ?
N2B C2B S2B 121.9(2) . . ?
N3B C2B S2B 111.6(2) . . ?
N1B C3B N3B 126.0(3) . . ?
N1B C3B S3B 120.7(2) . . ?
N3B C3B S3B 113.3(2) . . ?
C9B C4B C5B 120.1(3) . . ?
C9B C4B S1B 123.6(3) . . ?
C5B C4B S1B 116.1(3) . . ?
C6B C5B C4B 120.0(4) . . ?
C6B C5B H5BA 120.0 . . ?
C4B C5B H5BA 120.0 . . ?
C7B C6B C5B 119.5(4) . . ?
C7B C6B H6BA 120.2 . . ?
C5B C6B H6BA 120.2 . . ?
C8B C7B C6B 120.4(4) . . ?
C8B C7B H7BA 119.8 . . ?
C6B C7B H7BA 119.8 . . ?
C7B C8B C9B 120.2(4) . . ?
C7B C8B H8BA 119.9 . . ?
C9B C8B H8BA 119.9 . . ?
C4B C9B C8B 119.8(4) . . ?
C4B C9B H9BA 120.1 . . ?
C8B C9B H9BA 120.1 . . ?
C15B C10B C11B 121.4(3) . . ?
C15B C10B S2B 121.8(3) . . ?
C11B C10B S2B 116.7(3) . . ?
C12B C11B C10B 119.2(3) . . ?
C12B C11B H11B 120.4 . . ?
C10B C11B H11B 120.4 . . ?
C11B C12B C13B 120.2(3) . . ?
C11B C12B H12B 119.9 . . ?
C13B C12B H12B 119.9 . . ?
C14B C13B C12B 119.6(3) . . ?
C14B C13B H13B 120.2 . . ?
C12B C13B H13B 120.2 . . ?
C13B C14B C15B 121.0(3) . . ?
C13B C14B H14B 119.5 . . ?
C15B C14B H14B 119.5 . . ?
C10B C15B C14B 118.6(3) . . ?
C10B C15B H15B 120.7 . . ?
C14B C15B H15B 120.7 . . ?
C21B C16B C17B 120.9(3) . . ?
C21B C16B S3B 120.0(2) . . ?
C17B C16B S3B 119.0(2) . . ?
C18B C17B C16B 118.5(3) . . ?
C18B C17B H17B 120.8 . . ?
C16B C17B H17B 120.8 . . ?
C19B C18B C17B 120.3(3) . . ?
C19B C18B H18B 119.8 . . ?
C17B C18B H18B 119.8 . . ?
C20B C19B C18B 120.2(3) . . ?
C20B C19B H19B 119.9 . . ?
C18B C19B H19B 119.9 . . ?
C21B C20B C19B 120.4(4) . . ?
C21B C20B H20B 119.8 . . ?
C19B C20B H20B 119.8 . . ?
C20B C21B C16B 119.7(3) . . ?
C20B C21B H21B 120.2 . . ?
C16B C21B H21B 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3A N1A C1A N2A 2.6(4) . . . . ?
C3A N1A C1A S1A -177.9(2) . . . . ?
C2A N2A C1A N1A -2.8(4) . . . . ?
C2A N2A C1A S1A 177.7(2) . . . . ?
C4A S1A C1A N1A 4.2(3) . . . . ?
C4A S1A C1A N2A -176.1(2) . . . . ?
C1A N2A C2A N3A 0.2(4) . . . . ?
C1A N2A C2A S2A -179.5(2) . . . . ?
C3A N3A C2A N2A 2.0(4) . . . . ?
C3A N3A C2A S2A -178.2(2) . . . . ?
C10A S2A C2A N2A -6.9(3) . . . . ?
C10A S2A C2A N3A 173.3(2) . . . . ?
C2A N3A C3A N1A -2.2(5) . . . . ?
C2A N3A C3A S3A 177.4(2) . . . . ?
C1A N1A C3A N3A 0.2(4) . . . . ?
C1A N1A C3A S3A -179.5(2) . . . . ?
C16A S3A C3A N3A 177.4(2) . . . . ?
C16A S3A C3A N1A -2.9(3) . . . . ?
C1A S1A C4A C5A 119.2(3) . . . . ?
C1A S1A C4A C9A -65.6(3) . . . . ?
C9A C4A C5A C6A 0.5(5) . . . . ?
S1A C4A C5A C6A 175.7(2) . . . . ?
C4A C5A C6A C7A -0.7(5) . . . . ?
C5A C6A C7A C8A 0.6(5) . . . . ?
C6A C7A C8A C9A -0.3(5) . . . . ?
C7A C8A C9A C4A 0.1(5) . . . . ?
C5A C4A C9A C8A -0.2(5) . . . . ?
S1A C4A C9A C8A -175.3(2) . . . . ?
C2A S2A C10A C11A 117.1(3) . . . . ?
C2A S2A C10A C15A -68.8(3) . . . . ?
C15A C10A C11A C12A -1.1(5) . . . . ?
S2A C10A C11A C12A 173.1(3) . . . . ?
C10A C11A C12A C13A 1.3(6) . . . . ?
C11A C12A C13A C14A -0.3(6) . . . . ?
C12A C13A C14A C15A -0.9(6) . . . . ?
C13A C14A C15A C10A 1.1(5) . . . . ?
C11A C10A C15A C14A -0.1(5) . . . . ?
S2A C10A C15A C14A -174.2(3) . . . . ?
C3A S3A C16A C21A 94.7(3) . . . . ?
C3A S3A C16A C17A -92.4(3) . . . . ?
C21A C16A C17A C18A -2.8(5) . . . . ?
S3A C16A C17A C18A -175.9(3) . . . . ?
C16A C17A C18A C19A 1.1(5) . . . . ?
C17A C18A C19A C20A 0.5(5) . . . . ?
C18A C19A C20A C21A -0.3(5) . . . . ?
C19A C20A C21A C16A -1.5(5) . . . . ?
C17A C16A C21A C20A 3.0(5) . . . . ?
S3A C16A C21A C20A 176.0(3) . . . . ?
C3B N1B C1B N2B -0.7(4) . . . . ?
C3B N1B C1B S1B 179.3(2) . . . . ?
C2B N2B C1B N1B 4.3(4) . . . . ?
C2B N2B C1B S1B -175.7(2) . . . . ?
C4B S1B C1B N1B -7.5(3) . . . . ?
C4B S1B C1B N2B 172.6(2) . . . . ?
C1B N2B C2B N3B -3.9(4) . . . . ?
C1B N2B C2B S2B 175.2(2) . . . . ?
C3B N3B C2B N2B 0.0(4) . . . . ?
C3B N3B C2B S2B -179.2(2) . . . . ?
C10B S2B C2B N2B 0.8(3) . . . . ?
C10B S2B C2B N3B 180.0(2) . . . . ?
C1B N1B C3B N3B -4.0(4) . . . . ?
C1B N1B C3B S3B 176.8(2) . . . . ?
C2B N3B C3B N1B 4.4(4) . . . . ?
C2B N3B C3B S3B -176.4(2) . . . . ?
C16B S3B C3B N1B -3.2(3) . . . . ?
C16B S3B C3B N3B 177.5(2) . . . . ?
C1B S1B C4B C9B 59.9(3) . . . . ?
C1B S1B C4B C5B -125.8(2) . . . . ?
C9B C4B C5B C6B -1.0(5) . . . . ?
S1B C4B C5B C6B -175.4(3) . . . . ?
C4B C5B C6B C7B 0.6(5) . . . . ?
C5B C6B C7B C8B 0.0(6) . . . . ?
C6B C7B C8B C9B -0.3(5) . . . . ?
C5B C4B C9B C8B 0.7(5) . . . . ?
S1B C4B C9B C8B 174.7(2) . . . . ?
C7B C8B C9B C4B -0.1(5) . . . . ?
C2B S2B C10B C15B -68.0(3) . . . . ?
C2B S2B C10B C11B 116.6(3) . . . . ?
C15B C10B C11B C12B -0.1(5) . . . . ?
S2B C10B C11B C12B 175.3(2) . . . . ?
C10B C11B C12B C13B 0.1(5) . . . . ?
C11B C12B C13B C14B 0.5(5) . . . . ?
C12B C13B C14B C15B -1.1(5) . . . . ?
C11B C10B C15B C14B -0.4(5) . . . . ?
S2B C10B C15B C14B -175.6(2) . . . . ?
C13B C14B C15B C10B 1.1(5) . . . . ?
C3B S3B C16B C21B 93.0(3) . . . . ?
C3B S3B C16B C17B -90.3(3) . . . . ?
C21B C16B C17B C18B 1.2(5) . . . . ?
S3B C16B C17B C18B -175.4(2) . . . . ?
C16B C17B C18B C19B -0.5(5) . . . . ?
C17B C18B C19B C20B -1.7(5) . . . . ?
C18B C19B C20B C21B 3.1(5) . . . . ?
C19B C20B C21B C16B -2.3(5) . . . . ?
C17B C16B C21B C20B 0.1(4) . . . . ?
S3B C16B C21B C20B 176.7(2) . . . . ?

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
C11B H11B S3B 0.95 3.02 3.691(4) 128.9 5_766

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.073



####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1403547'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2,4,6-tris(p-tolylthio)-1,3,5-triazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N3 S3'
_chemical_formula_sum            'C24 H21 N3 S3'
_chemical_formula_weight         447.62

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   'P 21/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                   7.5595(16)
_cell_length_b                   9.694(2)
_cell_length_c                   29.683(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.753(4)
_cell_angle_gamma                90.00
_cell_volume                     2160.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3530
_cell_measurement_theta_min      2.212
_cell_measurement_theta_max      27.240
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(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  'Bruker Apex 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13058
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         28.37
_reflns_number_total             4982
_reflns_number_gt                3767
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex 2'
_computing_cell_refinement       'Bruker Apex 2'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'Sir92 (Altomare et al. 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'

_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)+(0.0753P)²+1.2768P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4982
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.02836(9) 0.46163(7) 0.44236(2) 0.02483(18) Uani 1 1 d . . .
S2 S 0.57524(9) 0.76455(8) 0.48418(2) 0.02847(19) Uani 1 1 d . . .
S3 S 0.29893(8) 0.71918(7) 0.30893(2) 0.02185(18) Uani 1 1 d . . .
N1 N 0.1703(3) 0.6047(2) 0.37672(7) 0.0209(4) Uani 1 1 d . . .
N2 N 0.3037(3) 0.6160(2) 0.45384(7) 0.0222(5) Uani 1 1 d . . .
N3 N 0.4323(3) 0.7413(2) 0.39672(7) 0.0208(5) Uani 1 1 d . . .
C1 C 0.1791(3) 0.5733(2) 0.42081(8) 0.0206(5) Uani 1 1 d . . .
C2 C 0.4237(3) 0.7013(3) 0.43957(8) 0.0205(5) Uani 1 1 d . . .
C3 C 0.3034(3) 0.6876(2) 0.36728(8) 0.0198(5) Uani 1 1 d . . .
C4 C -0.1568(3) 0.4320(2) 0.40079(8) 0.0205(5) Uani 1 1 d . . .
C5 C -0.3164(3) 0.4147(3) 0.41916(9) 0.0241(5) Uani 1 1 d . . .
H5A H -0.3218 0.4306 0.4505 0.029 Uiso 1 1 calc R . .
C6 C -0.4683(3) 0.3739(3) 0.39116(9) 0.0240(5) Uani 1 1 d . . .
H6A H -0.5765 0.3601 0.4039 0.029 Uiso 1 1 calc R . .
C7 C -0.4645(3) 0.3529(3) 0.34479(9) 0.0222(5) Uani 1 1 d . . .
C8 C -0.3038(3) 0.3715(3) 0.32727(8) 0.0224(5) Uani 1 1 d . . .
H8A H -0.2995 0.3581 0.2957 0.027 Uiso 1 1 calc R . .
C9 C -0.1487(3) 0.4093(3) 0.35454(8) 0.0213(5) Uani 1 1 d . . .
H9A H -0.0395 0.4195 0.3420 0.026 Uiso 1 1 calc R . .
C10 C -0.6306(3) 0.3104(3) 0.31465(9) 0.0282(6) Uani 1 1 d . . .
H10A H -0.6041 0.3038 0.2832 0.042 Uiso 1 1 calc R . .
H10B H -0.7242 0.3792 0.3167 0.042 Uiso 1 1 calc R . .
H10C H -0.6712 0.2205 0.3245 0.042 Uiso 1 1 calc R . .
C11 C 0.7328(3) 0.8619(3) 0.45766(8) 0.0234(5) Uani 1 1 d . . .
C12 C 0.9117(4) 0.8254(3) 0.46751(9) 0.0263(6) Uani 1 1 d . . .
H12A H 0.9436 0.7461 0.4855 0.032 Uiso 1 1 calc R . .
C13 C 1.0423(3) 0.9038(3) 0.45129(9) 0.0264(6) Uani 1 1 d . . .
H13A H 1.1640 0.8802 0.4592 0.032 Uiso 1 1 calc R . .
C14 C 0.9979(3) 1.0180(3) 0.42333(9) 0.0239(5) Uani 1 1 d . . .
C15 C 0.8191(4) 1.0522(3) 0.41352(9) 0.0268(6) Uani 1 1 d . . .
H15A H 0.7866 1.1288 0.3944 0.032 Uiso 1 1 calc R . .
C16 C 0.6869(4) 0.9770(3) 0.43108(9) 0.0279(6) Uani 1 1 d . . .
H16A H 0.5658 1.0042 0.4249 0.034 Uiso 1 1 calc R . .
C17 C 1.1437(4) 1.0994(3) 0.40499(10) 0.0313(6) Uani 1 1 d . . .
H17A H 1.0909 1.1743 0.3857 0.047 Uiso 1 1 calc R . .
H17B H 1.2118 1.0385 0.3871 0.047 Uiso 1 1 calc R . .
H17C H 1.2233 1.1382 0.4303 0.047 Uiso 1 1 calc R . .
C18 C 0.4943(3) 0.8175(3) 0.30475(8) 0.0223(5) Uani 1 1 d . . .
C19 C 0.6629(3) 0.7693(3) 0.32167(9) 0.0240(5) Uani 1 1 d . . .
H19A H 0.6756 0.6838 0.3373 0.029 Uiso 1 1 calc R . .
C20 C 0.8111(3) 0.8471(3) 0.31546(8) 0.0247(6) Uani 1 1 d . . .
H20A H 0.9255 0.8149 0.3276 0.030 Uiso 1 1 calc R . .
C21 C 0.7973(3) 0.9718(3) 0.29185(8) 0.0224(5) Uani 1 1 d . . .
C22 C 0.6279(3) 1.0165(3) 0.27431(8) 0.0228(5) Uani 1 1 d . . .
H22A H 0.6155 1.1000 0.2575 0.027 Uiso 1 1 calc R . .
C23 C 0.4773(3) 0.9415(3) 0.28094(8) 0.0218(5) Uani 1 1 d . . .
H23A H 0.3627 0.9745 0.2693 0.026 Uiso 1 1 calc R . .
C24 C 0.9599(4) 1.0545(3) 0.28461(10) 0.0297(6) Uani 1 1 d . . .
H24A H 0.9450 1.1496 0.2946 0.045 Uiso 1 1 calc R . .
H24B H 0.9759 1.0539 0.2523 0.045 Uiso 1 1 calc R . .
H24C H 1.0649 1.0137 0.3022 0.045 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.746(3) . ?
S1 C4 1.777(2) . ?
S2 C2 1.756(2) . ?
S2 C11 1.774(3) . ?
S3 C3 1.755(3) . ?
S3 C18 1.774(3) . ?
N1 C1 1.338(3) . ?
N1 C3 1.343(3) . ?
N2 C2 1.333(3) . ?
N2 C1 1.343(3) . ?
N3 C3 1.335(3) . ?
N3 C2 1.339(3) . ?
C4 C5 1.391(3) . ?
C4 C9 1.399(3) . ?
C5 C6 1.393(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.395(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.388(4) . ?
C7 C10 1.511(3) . ?
C8 C9 1.393(3) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.387(4) . ?
C11 C12 1.396(4) . ?
C12 C13 1.377(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.400(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.389(4) . ?
C14 C17 1.508(4) . ?
C15 C16 1.387(4) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.393(4) . ?
C18 C19 1.394(4) . ?
C19 C20 1.381(4) . ?
C19 H19A 0.9500 . ?
C20 C21 1.395(4) . ?
C20 H20A 0.9500 . ?
C21 C22 1.393(4) . ?
C21 C24 1.504(3) . ?
C22 C23 1.384(3) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 109.89(12) . . ?
C2 S2 C11 105.28(12) . . ?
C3 S3 C18 104.05(12) . . ?
C1 N1 C3 112.9(2) . . ?
C2 N2 C1 113.9(2) . . ?
C3 N3 C2 113.3(2) . . ?
N1 C1 N2 126.4(2) . . ?
N1 C1 S1 122.70(19) . . ?
N2 C1 S1 110.83(18) . . ?
N2 C2 N3 126.3(2) . . ?
N2 C2 S2 112.64(18) . . ?
N3 C2 S2 120.99(19) . . ?
N3 C3 N1 127.1(2) . . ?
N3 C3 S3 120.40(18) . . ?
N1 C3 S3 112.46(18) . . ?
C5 C4 C9 120.4(2) . . ?
C5 C4 S1 113.33(19) . . ?
C9 C4 S1 125.81(19) . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C5 C6 C7 121.3(2) . . ?
C5 C6 H6A 119.4 . . ?
C7 C6 H6A 119.4 . . ?
C8 C7 C6 118.1(2) . . ?
C8 C7 C10 121.1(2) . . ?
C6 C7 C10 120.8(2) . . ?
C7 C8 C9 122.0(2) . . ?
C7 C8 H8A 119.0 . . ?
C9 C8 H8A 119.0 . . ?
C8 C9 C4 118.7(2) . . ?
C8 C9 H9A 120.6 . . ?
C4 C9 H9A 120.6 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 119.6(2) . . ?
C16 C11 S2 123.0(2) . . ?
C12 C11 S2 117.2(2) . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C12 C13 C14 120.8(2) . . ?
C12 C13 H13A 119.6 . . ?
C14 C13 H13A 119.6 . . ?
C15 C14 C13 118.2(2) . . ?
C15 C14 C17 122.3(2) . . ?
C13 C14 C17 119.5(2) . . ?
C16 C15 C14 121.5(2) . . ?
C16 C15 H15A 119.3 . . ?
C14 C15 H15A 119.3 . . ?
C15 C16 C11 119.6(2) . . ?
C15 C16 H16A 120.2 . . ?
C11 C16 H16A 120.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 119.9(2) . . ?
C23 C18 S3 118.10(19) . . ?
C19 C18 S3 121.9(2) . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
C19 C20 C21 121.8(2) . . ?
C19 C20 H20A 119.1 . . ?
C21 C20 H20A 119.1 . . ?
C22 C21 C20 117.9(2) . . ?
C22 C21 C24 120.8(2) . . ?
C20 C21 C24 121.3(2) . . ?
C23 C22 C21 121.2(2) . . ?
C23 C22 H22A 119.4 . . ?
C21 C22 H22A 119.4 . . ?
C22 C23 C18 119.8(2) . . ?
C22 C23 H23A 120.1 . . ?
C18 C23 H23A 120.1 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C3 N1 C1 N2 -0.1(4) . . . . ?
C3 N1 C1 S1 -177.32(18) . . . . ?
C2 N2 C1 N1 2.2(4) . . . . ?
C2 N2 C1 S1 179.71(17) . . . . ?
C4 S1 C1 N1 -13.1(2) . . . . ?
C4 S1 C1 N2 169.27(17) . . . . ?
C1 N2 C2 N3 -2.5(4) . . . . ?
C1 N2 C2 S2 175.83(17) . . . . ?
C3 N3 C2 N2 0.6(4) . . . . ?
C3 N3 C2 S2 -177.60(18) . . . . ?
C11 S2 C2 N2 174.93(18) . . . . ?
C11 S2 C2 N3 -6.7(2) . . . . ?
C2 N3 C3 N1 2.0(4) . . . . ?
C2 N3 C3 S3 -176.20(18) . . . . ?
C1 N1 C3 N3 -2.2(4) . . . . ?
C1 N1 C3 S3 176.12(17) . . . . ?
C18 S3 C3 N3 3.0(2) . . . . ?
C18 S3 C3 N1 -175.43(18) . . . . ?
C1 S1 C4 C5 -146.10(19) . . . . ?
C1 S1 C4 C9 42.0(3) . . . . ?
C9 C4 C5 C6 0.3(4) . . . . ?
S1 C4 C5 C6 -172.10(19) . . . . ?
C4 C5 C6 C7 -1.4(4) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?
C5 C6 C7 C10 -179.2(2) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C10 C7 C8 C9 -179.3(2) . . . . ?
C7 C8 C9 C4 -1.4(4) . . . . ?
C5 C4 C9 C8 1.1(4) . . . . ?
S1 C4 C9 C8 172.48(19) . . . . ?
C2 S2 C11 C16 61.3(2) . . . . ?
C2 S2 C11 C12 -123.9(2) . . . . ?
C16 C11 C12 C13 0.6(4) . . . . ?
S2 C11 C12 C13 -174.3(2) . . . . ?
C11 C12 C13 C14 -2.5(4) . . . . ?
C12 C13 C14 C15 1.8(4) . . . . ?
C12 C13 C14 C17 -178.2(2) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C17 C14 C15 C16 -179.3(2) . . . . ?
C14 C15 C16 C11 -2.5(4) . . . . ?
C12 C11 C16 C15 1.8(4) . . . . ?
S2 C11 C16 C15 176.5(2) . . . . ?
C3 S3 C18 C23 -128.0(2) . . . . ?
C3 S3 C18 C19 56.6(2) . . . . ?
C23 C18 C19 C20 1.5(4) . . . . ?
S3 C18 C19 C20 176.77(19) . . . . ?
C18 C19 C20 C21 -1.3(4) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C19 C20 C21 C24 -178.9(2) . . . . ?
C20 C21 C22 C23 1.5(4) . . . . ?
C24 C21 C22 C23 -179.7(2) . . . . ?
C21 C22 C23 C18 -1.3(4) . . . . ?
C19 C18 C23 C22 -0.2(4) . . . . ?
S3 C18 C23 C22 -175.66(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.098
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1403548'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2,4,6-tris((4-chlorophenyl)thio)-1,3,5-triazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H12 Cl3 N3 S3'
_chemical_formula_sum            'C21 H12 Cl3 N3 S3'
_chemical_formula_weight         508.87

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'
Cl Cl 0.1484 0.1585 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

loop_
_space_group_symop_operation_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                   10.233(3)
_cell_length_b                   14.350(4)
_cell_length_c                   14.563(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.980(5)
_cell_angle_gamma                90
_cell_volume                     2138.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2926
_cell_measurement_theta_min      2.797
_cell_measurement_theta_max      26.857
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.737
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12975
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.993
_diffrn_reflns_theta_max         28.391
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4952
_reflns_number_gt                3554
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker Apex 2'
_computing_cell_refinement       'Bruker Apex 2'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'Sir92 (Altomare et a. 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²+0.6679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4952
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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_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
Cl1 Cl 0.44793(8) -0.11593(5) 0.37374(5) 0.0315(2) Uani 1 1 d . . . . .
Cl2 Cl 0.38715(8) 0.83369(6) 0.80323(5) 0.0343(2) Uani 1 1 d . . . . .
Cl3 Cl 0.56258(9) 0.66046(5) 0.92958(5) 0.0348(2) Uani 1 1 d . . . . .
S1 S 0.15083(7) 0.26487(5) 0.35743(5) 0.02562(19) Uani 1 1 d . . . . .
S2 S 0.14488(8) 0.60214(5) 0.47778(5) 0.02630(19) Uani 1 1 d . . . . .
S3 S 0.47215(7) 0.35392(5) 0.63071(5) 0.02357(18) Uani 1 1 d . . . . .
N1 N 0.3156(2) 0.31945(15) 0.49366(15) 0.0217(5) Uani 1 1 d . . . . .
N2 N 0.1651(2) 0.42924(16) 0.42866(15) 0.0228(5) Uani 1 1 d . . . . .
N3 N 0.3061(2) 0.47528(15) 0.55242(15) 0.0203(5) Uani 1 1 d . . . . .
C1 C 0.2204(3) 0.34436(19) 0.43553(19) 0.0210(6) Uani 1 1 d . . . . .
C2 C 0.2139(3) 0.49095(19) 0.48871(19) 0.0216(6) Uani 1 1 d . . . . .
C3 C 0.3512(3) 0.38797(19) 0.55095(19) 0.0213(6) Uani 1 1 d . . . . .
C4 C 0.2452(3) 0.16139(19) 0.36935(19) 0.0218(6) Uani 1 1 d . . . . .
C5 C 0.2898(3) 0.1230(2) 0.28824(19) 0.0237(6) Uani 1 1 d . . . . .
H5A H 0.2782 0.1557 0.2320 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3516(3) 0.0368(2) 0.2893(2) 0.0254(6) Uani 1 1 d . . . . .
H6A H 0.3807 0.0094 0.2339 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3699(3) -0.00818(18) 0.3723(2) 0.0230(6) Uani 1 1 d . . . . .
C8 C 0.3261(3) 0.0301(2) 0.4538(2) 0.0270(7) Uani 1 1 d . . . . .
H8A H 0.3401 -0.0020 0.5102 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2626(3) 0.1146(2) 0.45253(19) 0.0250(6) Uani 1 1 d . . . . .
H9A H 0.2309 0.1407 0.5078 0.030 Uiso 1 1 calc R U . . .
C10 C 0.2192(3) 0.66283(19) 0.57127(19) 0.0224(6) Uani 1 1 d . . . . .
C11 C 0.3098(3) 0.7319(2) 0.5534(2) 0.0261(7) Uani 1 1 d . . . . .
H11A H 0.3354 0.7433 0.4920 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3634(3) 0.7844(2) 0.6246(2) 0.0264(7) Uani 1 1 d . . . . .
H12A H 0.4256 0.8318 0.6126 0.032 Uiso 1 1 calc R U . . .
C13 C 0.3244(3) 0.7662(2) 0.71347(19) 0.0245(6) Uani 1 1 d . . . . .
C14 C 0.2355(3) 0.6966(2) 0.7326(2) 0.0261(6) Uani 1 1 d . . . . .
H14A H 0.2112 0.6845 0.7942 0.031 Uiso 1 1 calc R U . . .
C15 C 0.1827(3) 0.64508(19) 0.6613(2) 0.0246(6) Uani 1 1 d . . . . .
H15A H 0.1212 0.5973 0.6736 0.030 Uiso 1 1 calc R U . . .
C16 C 0.4805(3) 0.4480(2) 0.70944(19) 0.0219(6) Uani 1 1 d . . . . .
C17 C 0.5357(3) 0.5332(2) 0.6867(2) 0.0248(6) Uani 1 1 d . . . . .
H17A H 0.5582 0.5456 0.6249 0.030 Uiso 1 1 calc R U . . .
C18 C 0.5580(3) 0.59983(19) 0.7535(2) 0.0254(6) Uani 1 1 d . . . . .
H18A H 0.5959 0.6581 0.7381 0.030 Uiso 1 1 calc R U . . .
C19 C 0.5245(3) 0.58073(19) 0.84308(19) 0.0236(6) Uani 1 1 d . . . . .
C20 C 0.4644(3) 0.4980(2) 0.8665(2) 0.0264(7) Uani 1 1 d . . . . .
H20A H 0.4378 0.4872 0.9277 0.032 Uiso 1 1 calc R U . . .
C21 C 0.4434(3) 0.43107(19) 0.79948(19) 0.0236(6) Uani 1 1 d . . . . .
H21A H 0.4035 0.3735 0.8149 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.740(3) . ?
Cl2 C13 1.741(3) . ?
Cl3 C19 1.741(3) . ?
S1 C1 1.753(3) . ?
S1 C4 1.778(3) . ?
S2 C2 1.751(3) . ?
S2 C10 1.776(3) . ?
S3 C3 1.752(3) . ?
S3 C16 1.772(3) . ?
N1 C1 1.329(4) . ?
N1 C3 1.336(3) . ?
N2 C2 1.336(4) . ?
N2 C1 1.346(3) . ?
N3 C2 1.331(4) . ?
N3 C3 1.336(3) . ?
C4 C5 1.388(4) . ?
C4 C9 1.394(4) . ?
C5 C6 1.389(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.380(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.389(4) . ?
C8 C9 1.376(4) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 C11 1.385(4) . ?
C10 C15 1.393(4) . ?
C11 C12 1.387(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.386(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(4) . ?
C14 C15 1.378(4) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.389(4) . ?
C16 C21 1.393(4) . ?
C17 C18 1.380(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.382(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.383(4) . ?
C20 C21 1.383(4) . ?
C20 H20A 0.9500 . ?
C21 H21A 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
C1 S1 C4 105.44(13) . . ?
C2 S2 C10 102.15(13) . . ?
C3 S3 C16 104.02(13) . . ?
C1 N1 C3 112.9(2) . . ?
C2 N2 C1 113.5(2) . . ?
C2 N3 C3 112.9(2) . . ?
N1 C1 N2 126.4(3) . . ?
N1 C1 S1 121.6(2) . . ?
N2 C1 S1 112.0(2) . . ?
N3 C2 N2 126.7(3) . . ?
N3 C2 S2 119.8(2) . . ?
N2 C2 S2 113.5(2) . . ?
N3 C3 N1 127.5(3) . . ?
N3 C3 S3 119.5(2) . . ?
N1 C3 S3 113.0(2) . . ?
C5 C4 C9 120.6(3) . . ?
C5 C4 S1 115.7(2) . . ?
C9 C4 S1 123.3(2) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C7 C6 C5 118.8(3) . . ?
C7 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 Cl1 118.8(2) . . ?
C8 C7 Cl1 119.7(2) . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C4 119.3(3) . . ?
C8 C9 H9A 120.3 . . ?
C4 C9 H9A 120.3 . . ?
C11 C10 C15 119.9(3) . . ?
C11 C10 S2 119.1(2) . . ?
C15 C10 S2 120.9(2) . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12A 120.7 . . ?
C11 C12 H12A 120.7 . . ?
C14 C13 C12 121.7(3) . . ?
C14 C13 Cl2 119.1(2) . . ?
C12 C13 Cl2 119.2(2) . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14A 120.5 . . ?
C13 C14 H14A 120.5 . . ?
C14 C15 C10 120.2(3) . . ?
C14 C15 H15A 119.9 . . ?
C10 C15 H15A 119.9 . . ?
C17 C16 C21 119.7(3) . . ?
C17 C16 S3 122.1(2) . . ?
C21 C16 S3 117.7(2) . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C17 C18 C19 119.1(3) . . ?
C17 C18 H18A 120.4 . . ?
C19 C18 H18A 120.4 . . ?
C18 C19 C20 121.4(3) . . ?
C18 C19 Cl3 119.8(2) . . ?
C20 C19 Cl3 118.8(2) . . ?
C21 C20 C19 119.1(3) . . ?
C21 C20 H20A 120.4 . . ?
C19 C20 H20A 120.4 . . ?
C20 C21 C16 120.1(3) . . ?
C20 C21 H21A 119.9 . . ?
C16 C21 H21A 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 2.7(4) . . . . ?
C3 N1 C1 S1 -176.7(2) . . . . ?
C2 N2 C1 N1 -0.8(4) . . . . ?
C2 N2 C1 S1 178.58(19) . . . . ?
C4 S1 C1 N1 -5.7(3) . . . . ?
C4 S1 C1 N2 174.9(2) . . . . ?
C3 N3 C2 N2 1.3(4) . . . . ?
C3 N3 C2 S2 -178.5(2) . . . . ?
C1 N2 C2 N3 -1.4(4) . . . . ?
C1 N2 C2 S2 178.4(2) . . . . ?
C10 S2 C2 N3 -4.8(3) . . . . ?
C10 S2 C2 N2 175.4(2) . . . . ?
C2 N3 C3 N1 1.1(4) . . . . ?
C2 N3 C3 S3 -179.38(19) . . . . ?
C1 N1 C3 N3 -2.8(4) . . . . ?
C1 N1 C3 S3 177.6(2) . . . . ?
C16 S3 C3 N3 10.4(3) . . . . ?
C16 S3 C3 N1 -170.0(2) . . . . ?
C1 S1 C4 C5 -130.0(2) . . . . ?
C1 S1 C4 C9 56.8(3) . . . . ?
C9 C4 C5 C6 0.6(4) . . . . ?
S1 C4 C5 C6 -172.7(2) . . . . ?
C4 C5 C6 C7 -1.5(4) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?
C5 C6 C7 Cl1 -179.7(2) . . . . ?
C6 C7 C8 C9 0.3(5) . . . . ?
Cl1 C7 C8 C9 -179.0(2) . . . . ?
C7 C8 C9 C4 -1.2(4) . . . . ?
C5 C4 C9 C8 0.8(4) . . . . ?
S1 C4 C9 C8 173.5(2) . . . . ?
C2 S2 C10 C11 110.3(2) . . . . ?
C2 S2 C10 C15 -72.9(3) . . . . ?
C15 C10 C11 C12 -0.8(4) . . . . ?
S2 C10 C11 C12 176.0(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C11 C12 C13 Cl2 -178.2(2) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
Cl2 C13 C14 C15 178.0(2) . . . . ?
C13 C14 C15 C10 0.3(4) . . . . ?
C11 C10 C15 C14 0.7(4) . . . . ?
S2 C10 C15 C14 -176.1(2) . . . . ?
C3 S3 C16 C17 -72.5(3) . . . . ?
C3 S3 C16 C21 114.7(2) . . . . ?
C21 C16 C17 C18 2.2(4) . . . . ?
S3 C16 C17 C18 -170.4(2) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 C20 -2.6(5) . . . . ?
C17 C18 C19 Cl3 175.4(2) . . . . ?
C18 C19 C20 C21 3.3(5) . . . . ?
Cl3 C19 C20 C21 -174.8(2) . . . . ?
C19 C20 C21 C16 -1.1(4) . . . . ?
C17 C16 C21 C20 -1.6(4) . . . . ?
S3 C16 C21 C20 171.3(2) . . . . ?

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
C6 H6A N2 0.95 2.67 3.531(4) 151.6 2_545
C11 H11A Cl1 0.95 2.90 3.706(3) 142.8 1_565
C11 H11A S3 0.95 3.02 3.726(3) 132.0 3_666
C20 H20A Cl3 0.95 2.97 3.754(3) 141.1 3_667

_refine_diff_density_max         0.739
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.111

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1403549'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2,4,6-tris((3-nitrophenyl)thio)-1,3,5-triazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H12 N6 O6 S3'
_chemical_formula_sum            'C21 H12 N6 O6 S3'
_chemical_formula_weight         540.55

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   20.799(4)
_cell_length_b                   7.8317(15)
_cell_length_c                   15.126(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.382(5)
_cell_angle_gamma                90
_cell_volume                     2324.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2748
_cell_measurement_theta_min      2.801
_cell_measurement_theta_max      21.848
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.371
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6666
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15610
_diffrn_reflns_av_unetI/netI     0.1562
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.800
_diffrn_reflns_theta_max         28.411
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5801
_reflns_number_gt                2283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker Apex 2'
_computing_cell_refinement       'Bruker Apex 2'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'Sir92 (Altomare et al. 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5801
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2272
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_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_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 0.48609(4) 0.66408(13) 0.33654(6) 0.0555(3) Uani 1 1 d . . . . .
S2 S 0.68106(5) 0.56167(15) 0.64158(7) 0.0693(4) Uani 1 1 d . . . . .
S3 S 0.71753(5) 0.42583(15) 0.31578(7) 0.0678(4) Uani 1 1 d . . . . .
O1 O 0.29172(18) 0.4859(5) -0.0587(3) 0.1290(15) Uani 1 1 d . . . . .
O2 O 0.28637(15) 0.3985(4) 0.0725(3) 0.1008(12) Uani 1 1 d . . . . .
O3 O 0.95357(18) 0.1521(4) 0.7788(3) 0.1236(14) Uani 1 1 d . . . . .
O4 O 0.85546(19) 0.0542(4) 0.7110(3) 0.1455(18) Uani 1 1 d . . . . .
O5 O 0.9650(2) 0.0167(5) 0.5728(3) 0.1589(18) Uani 1 1 d . . . . .
O6 O 0.8830(2) -0.0779(5) 0.4592(3) 0.1413(17) Uani 1 1 d . . . . .
N1 N 0.60600(13) 0.5384(3) 0.33366(19) 0.0452(7) Uani 1 1 d . . . . .
N2 N 0.59119(13) 0.6052(3) 0.47882(19) 0.0459(8) Uani 1 1 d . . . . .
N3 N 0.69673(12) 0.4915(3) 0.4771(2) 0.0422(7) Uani 1 1 d . . . . .
N4 N 0.31467(18) 0.4738(5) 0.0255(3) 0.0787(11) Uani 1 1 d . . . . .
N5 N 0.8932(2) 0.1707(5) 0.7376(3) 0.0762(11) Uani 1 1 d . . . . .
N6 N 0.9127(2) 0.0360(6) 0.5083(4) 0.1009(14) Uani 1 1 d . . . . .
C1 C 0.57048(15) 0.5926(4) 0.3863(3) 0.0397(8) Uani 1 1 d . . . . .
C2 C 0.65472(16) 0.5502(4) 0.5195(2) 0.0436(9) Uani 1 1 d . . . . .
C3 C 0.66972(16) 0.4914(4) 0.3848(3) 0.0433(9) Uani 1 1 d . . . . .
C4 C 0.46522(15) 0.6351(4) 0.2150(2) 0.0373(8) Uani 1 1 d . . . . .
C5 C 0.40328(15) 0.5590(4) 0.1694(2) 0.0432(9) Uani 1 1 d . . . . .
H5A H 0.3765 0.5125 0.2037 0.052 Uiso 1 1 calc R U . . .
C6 C 0.38124(17) 0.5521(4) 0.0737(3) 0.0466(9) Uani 1 1 d . . . . .
C7 C 0.4190(2) 0.6114(5) 0.0219(3) 0.0630(11) Uani 1 1 d . . . . .
H7A H 0.4027 0.6033 -0.0446 0.076 Uiso 1 1 calc R U . . .
C8 C 0.48122(19) 0.6830(5) 0.0683(3) 0.0648(11) Uani 1 1 d . . . . .
H8A H 0.5087 0.7241 0.0336 0.078 Uiso 1 1 calc R U . . .
C9 C 0.50413(17) 0.6962(4) 0.1631(3) 0.0509(10) Uani 1 1 d . . . . .
H9A H 0.5471 0.7475 0.1941 0.061 Uiso 1 1 calc R U . . .
C10 C 0.77013(17) 0.5250(5) 0.6756(2) 0.0509(10) Uani 1 1 d . . . . .
C11 C 0.8128(2) 0.6628(5) 0.6968(3) 0.0775(13) Uani 1 1 d . . . . .
H11A H 0.7947 0.7752 0.6886 0.093 Uiso 1 1 calc R U . . .
C12 C 0.8823(2) 0.6378(6) 0.7302(3) 0.0918(16) Uani 1 1 d . . . . .
H12A H 0.9120 0.7337 0.7440 0.110 Uiso 1 1 calc R U . . .
C13 C 0.90875(18) 0.4786(6) 0.7434(3) 0.0675(12) Uani 1 1 d . . . . .
H13A H 0.9566 0.4616 0.7677 0.081 Uiso 1 1 calc R U . . .
C14 C 0.86543(18) 0.3435(5) 0.7213(2) 0.0509(10) Uani 1 1 d . . . . .
C15 C 0.79557(17) 0.3611(5) 0.6862(2) 0.0498(10) Uani 1 1 d . . . . .
H15A H 0.7663 0.2646 0.6701 0.060 Uiso 1 1 calc R U . . .
C16 C 0.79887(17) 0.3937(5) 0.4006(3) 0.0532(10) Uani 1 1 d . . . . .
C17 C 0.8385(2) 0.5320(5) 0.4409(3) 0.0736(13) Uani 1 1 d . . . . .
H17A H 0.8217 0.6446 0.4250 0.088 Uiso 1 1 calc R U . . .
C18 C 0.9033(2) 0.5064(6) 0.5047(3) 0.0820(14) Uani 1 1 d . . . . .
H18A H 0.9305 0.6017 0.5335 0.098 Uiso 1 1 calc R U . . .
C19 C 0.9280(2) 0.3457(7) 0.5262(3) 0.0779(13) Uani 1 1 d . . . . .
H19A H 0.9727 0.3279 0.5689 0.094 Uiso 1 1 calc R U . . .
C20 C 0.8880(2) 0.2102(6) 0.4859(3) 0.0612(11) Uani 1 1 d . . . . .
C21 C 0.82326(17) 0.2312(5) 0.4228(2) 0.0521(10) Uani 1 1 d . . . . .
H21A H 0.7961 0.1351 0.3952 0.062 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.756(3) . ?
S1 C4 1.758(3) . ?
S2 C2 1.746(3) . ?
S2 C10 1.774(3) . ?
S3 C3 1.741(3) . ?
S3 C16 1.770(4) . ?
O1 N4 1.205(4) . ?
O2 N4 1.216(4) . ?
O3 N5 1.211(4) . ?
O4 N5 1.183(4) . ?
O5 N6 1.206(5) . ?
O6 N6 1.194(5) . ?
N1 C1 1.323(4) . ?
N1 C3 1.345(4) . ?
N2 C1 1.325(4) . ?
N2 C2 1.330(4) . ?
N3 C3 1.320(4) . ?
N3 C2 1.326(4) . ?
N4 C6 1.468(4) . ?
N5 C14 1.460(5) . ?
N6 C20 1.458(5) . ?
C4 C5 1.379(4) . ?
C4 C9 1.386(4) . ?
C5 C6 1.367(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.362(5) . ?
C7 C8 1.370(5) . ?
C7 H7A 0.9500 . ?
C8 C9 1.357(4) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 C11 1.367(5) . ?
C10 C15 1.377(5) . ?
C11 C12 1.377(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.350(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.358(5) . ?
C13 H13A 0.9500 . ?
C14 C15 1.378(4) . ?
C15 H15A 0.9500 . ?
C16 C21 1.370(5) . ?
C16 C17 1.375(5) . ?
C17 C18 1.386(5) . ?
C17 H17A 0.9500 . ?
C18 C19 1.358(5) . ?
C18 H18A 0.9500 . ?
C19 C20 1.360(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.378(4) . ?
C21 H21A 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
C1 S1 C4 105.77(16) . . ?
C2 S2 C10 103.26(17) . . ?
C3 S3 C16 101.88(17) . . ?
C1 N1 C3 112.5(3) . . ?
C1 N2 C2 112.9(3) . . ?
C3 N3 C2 113.2(3) . . ?
O1 N4 O2 123.9(4) . . ?
O1 N4 C6 118.0(4) . . ?
O2 N4 C6 118.2(4) . . ?
O4 N5 O3 122.7(4) . . ?
O4 N5 C14 118.4(4) . . ?
O3 N5 C14 118.9(4) . . ?
O6 N6 O5 123.5(5) . . ?
O6 N6 C20 119.0(5) . . ?
O5 N6 C20 117.3(5) . . ?
N1 C1 N2 127.5(3) . . ?
N1 C1 S1 121.5(3) . . ?
N2 C1 S1 110.9(2) . . ?
N3 C2 N2 127.0(3) . . ?
N3 C2 S2 120.2(3) . . ?
N2 C2 S2 112.8(3) . . ?
N3 C3 N1 126.9(3) . . ?
N3 C3 S3 120.4(3) . . ?
N1 C3 S3 112.7(3) . . ?
C5 C4 C9 119.3(3) . . ?
C5 C4 S1 116.4(2) . . ?
C9 C4 S1 124.0(3) . . ?
C6 C5 C4 118.4(3) . . ?
C6 C5 H5A 120.8 . . ?
C4 C5 H5A 120.8 . . ?
C7 C6 C5 122.7(3) . . ?
C7 C6 N4 119.1(4) . . ?
C5 C6 N4 118.2(4) . . ?
C6 C7 C8 118.2(3) . . ?
C6 C7 H7A 120.9 . . ?
C8 C7 H7A 120.9 . . ?
C9 C8 C7 120.9(4) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C8 C9 C4 120.4(3) . . ?
C8 C9 H9A 119.8 . . ?
C4 C9 H9A 119.8 . . ?
C11 C10 C15 120.9(3) . . ?
C11 C10 S2 118.4(3) . . ?
C15 C10 S2 120.6(3) . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C12 C13 C14 118.6(4) . . ?
C12 C13 H13A 120.7 . . ?
C14 C13 H13A 120.7 . . ?
C13 C14 C15 123.1(4) . . ?
C13 C14 N5 119.2(4) . . ?
C15 C14 N5 117.7(4) . . ?
C10 C15 C14 117.0(3) . . ?
C10 C15 H15A 121.5 . . ?
C14 C15 H15A 121.5 . . ?
C21 C16 C17 120.3(4) . . ?
C21 C16 S3 119.8(3) . . ?
C17 C16 S3 119.9(3) . . ?
C16 C17 C18 119.7(4) . . ?
C16 C17 H17A 120.1 . . ?
C18 C17 H17A 120.1 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C18 C19 C20 119.3(4) . . ?
C18 C19 H19A 120.4 . . ?
C20 C19 H19A 120.4 . . ?
C19 C20 C21 121.9(4) . . ?
C19 C20 N6 120.7(4) . . ?
C21 C20 N6 117.4(4) . . ?
C16 C21 C20 118.5(4) . . ?
C16 C21 H21A 120.7 . . ?
C20 C21 H21A 120.7 . . ?

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
C3 N1 C1 N2 0.6(5) . . . . ?
C3 N1 C1 S1 179.2(2) . . . . ?
C2 N2 C1 N1 -2.2(5) . . . . ?
C2 N2 C1 S1 179.2(2) . . . . ?
C4 S1 C1 N1 2.7(3) . . . . ?
C4 S1 C1 N2 -178.6(2) . . . . ?
C3 N3 C2 N2 0.2(5) . . . . ?
C3 N3 C2 S2 -179.7(2) . . . . ?
C1 N2 C2 N3 1.7(5) . . . . ?
C1 N2 C2 S2 -178.4(2) . . . . ?
C10 S2 C2 N3 11.5(3) . . . . ?
C10 S2 C2 N2 -168.4(3) . . . . ?
C2 N3 C3 N1 -2.1(5) . . . . ?
C2 N3 C3 S3 177.9(2) . . . . ?
C1 N1 C3 N3 1.7(5) . . . . ?
C1 N1 C3 S3 -178.2(2) . . . . ?
C16 S3 C3 N3 -5.4(3) . . . . ?
C16 S3 C3 N1 174.6(2) . . . . ?
C1 S1 C4 C5 133.3(2) . . . . ?
C1 S1 C4 C9 -52.3(3) . . . . ?
C9 C4 C5 C6 -2.3(5) . . . . ?
S1 C4 C5 C6 172.4(2) . . . . ?
C4 C5 C6 C7 2.5(5) . . . . ?
C4 C5 C6 N4 -178.9(3) . . . . ?
O1 N4 C6 C7 -10.1(5) . . . . ?
O2 N4 C6 C7 168.9(4) . . . . ?
O1 N4 C6 C5 171.3(4) . . . . ?
O2 N4 C6 C5 -9.7(5) . . . . ?
C5 C6 C7 C8 -1.0(6) . . . . ?
N4 C6 C7 C8 -179.6(3) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C7 C8 C9 C4 0.8(6) . . . . ?
C5 C4 C9 C8 0.7(5) . . . . ?
S1 C4 C9 C8 -173.5(3) . . . . ?
C2 S2 C10 C11 98.8(3) . . . . ?
C2 S2 C10 C15 -85.4(3) . . . . ?
C15 C10 C11 C12 -0.7(6) . . . . ?
S2 C10 C11 C12 175.1(3) . . . . ?
C10 C11 C12 C13 -0.9(7) . . . . ?
C11 C12 C13 C14 1.4(7) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C12 C13 C14 N5 -178.4(4) . . . . ?
O4 N5 C14 C13 -173.9(4) . . . . ?
O3 N5 C14 C13 7.2(6) . . . . ?
O4 N5 C14 C15 7.8(6) . . . . ?
O3 N5 C14 C15 -171.1(4) . . . . ?
C11 C10 C15 C14 1.7(5) . . . . ?
S2 C10 C15 C14 -174.0(3) . . . . ?
C13 C14 C15 C10 -1.2(5) . . . . ?
N5 C14 C15 C10 176.9(3) . . . . ?
C3 S3 C16 C21 108.1(3) . . . . ?
C3 S3 C16 C17 -74.8(3) . . . . ?
C21 C16 C17 C18 -0.5(6) . . . . ?
S3 C16 C17 C18 -177.6(3) . . . . ?
C16 C17 C18 C19 1.2(6) . . . . ?
C17 C18 C19 C20 -1.3(7) . . . . ?
C18 C19 C20 C21 0.8(6) . . . . ?
C18 C19 C20 N6 -179.3(4) . . . . ?
O6 N6 C20 C19 -165.2(5) . . . . ?
O5 N6 C20 C19 10.3(7) . . . . ?
O6 N6 C20 C21 14.7(7) . . . . ?
O5 N6 C20 C21 -169.7(4) . . . . ?
C17 C16 C21 C20 0.0(5) . . . . ?
S3 C16 C21 C20 177.0(3) . . . . ?
C19 C20 C21 C16 -0.1(5) . . . . ?
N6 C20 C21 C16 179.9(3) . . . . ?

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
C5 H5A S2 0.95 3.02 3.934(4) 162.2 3_666
C11 H11A O4 0.95 2.49 3.179(5) 129.4 1_565
C13 H13A O5 0.95 2.46 3.141(6) 128.5 2_756
C17 H17A O6 0.95 2.49 3.177(6) 129.6 1_565

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.193
_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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1403550'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2,4,6-tris((2-methyl-5-nitrophenyl)thio)-1,3,5-triazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 N6 O6 S3'
_chemical_formula_sum            'C24 H18 N6 O6 S3'
_chemical_formula_weight         582.62

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

loop_
_space_group_symop_operation_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                   12.642(3)
_cell_length_b                   8.916(2)
_cell_length_c                   23.281(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.804(6)
_cell_angle_gamma                90
_cell_volume                     2599.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3830
_cell_measurement_theta_min      2.449
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.338
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18042
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.449
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4706
_reflns_number_gt                2867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker Apex 2'
_computing_cell_refinement       'Bruker Apex 2'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'Sir92 (Altomare et al. 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+0.7155P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4706
_refine_ls_number_parameters     391
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.038
_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_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 0.69009(7) 0.24991(10) 0.16197(3) 0.0681(3) Uani 1 1 d D . . . .
S2 S 0.63098(6) 0.41049(9) 0.36640(3) 0.0586(2) Uani 1 1 d . . . . .
S3 S 0.42618(6) 0.69900(10) 0.18364(3) 0.0600(2) Uani 1 1 d . . . . .
N5 N 0.5563(2) 0.7973(3) 0.51876(9) 0.0634(7) Uani 1 1 d D . . . .
O3 O 0.65269(18) 0.8058(3) 0.52970(9) 0.0941(8) Uani 1 1 d D . . . .
O4 O 0.49485(19) 0.8639(3) 0.54547(9) 0.0966(8) Uani 1 1 d D . . . .
N6 N 0.18370(18) 0.7949(3) 0.34119(10) 0.0648(7) Uani 1 1 d D . . . .
O5 O 0.17129(18) 0.8458(3) 0.38809(9) 0.0848(7) Uani 1 1 d D . . . .
O6 O 0.12014(19) 0.7128(3) 0.31323(11) 0.1102(10) Uani 1 1 d D . . . .
N1 N 0.56215(17) 0.4827(3) 0.17784(8) 0.0466(6) Uani 1 1 d . . . . .
N2 N 0.65100(17) 0.3535(3) 0.26001(9) 0.0508(6) Uani 1 1 d . . . . .
N3 N 0.53423(17) 0.5556(2) 0.27308(8) 0.0429(6) Uani 1 1 d . . . . .
C1 C 0.6268(2) 0.3777(3) 0.20306(10) 0.0467(7) Uani 1 1 d . . . . .
C2 C 0.6011(2) 0.4468(3) 0.29194(10) 0.0425(7) Uani 1 1 d . . . . .
C3 C 0.5182(2) 0.5665(3) 0.21558(10) 0.0429(7) Uani 1 1 d . . . . .
N4 N 0.4098(4) 0.1621(6) -0.02338(17) 0.1088(19) Uani 0.608(3) 1 d D U P A 1
O1 O 0.3624(4) 0.0806(6) 0.00592(18) 0.1108(16) Uani 0.608(3) 1 d D U P A 1
O2 O 0.3887(4) 0.1758(7) -0.07557(16) 0.158(2) Uani 0.608(3) 1 d D U P A 1
C4 C 0.6338(4) 0.2782(6) 0.08876(16) 0.0423(10) Uani 0.608(3) 1 d D . P A 1
C5 C 0.6820(5) 0.3894(7) 0.0591(2) 0.0555(11) Uani 0.608(3) 1 d D . P A 1
C6 C 0.7736(6) 0.4817(9) 0.0871(4) 0.0885(17) Uani 0.608(3) 1 d D . P A 1
H6A H 0.8248 0.4168 0.1108 0.133 Uiso 0.608(3) 1 calc R U P A 1
H6B H 0.7472 0.5584 0.1118 0.133 Uiso 0.608(3) 1 calc R U P A 1
H6C H 0.8089 0.5304 0.0571 0.133 Uiso 0.608(3) 1 calc R U P A 1
C7 C 0.6389(6) 0.4148(11) 0.0023(3) 0.0896(14) Uani 0.608(3) 1 d D . P A 1
H7A H 0.6711 0.4876 -0.0196 0.108 Uiso 0.608(3) 1 calc R U P A 1
C8 C 0.5530(6) 0.3400(11) -0.0230(3) 0.1035(16) Uani 0.608(3) 1 d D . P A 1
H8A H 0.5304 0.3504 -0.0634 0.124 Uiso 0.608(3) 1 calc R U P A 1
C9 C 0.4959(4) 0.2450(6) 0.0109(3) 0.0810(16) Uani 0.608(3) 1 d D . P A 1
C10 C 0.5371(5) 0.2109(8) 0.0667(3) 0.0627(11) Uani 0.608(3) 1 d D . P A 1
H10A H 0.5014 0.1442 0.0895 0.075 Uiso 0.608(3) 1 calc R U P A 1
N4B N 0.4059(5) 0.1325(7) 0.0059(3) 0.1088(19) Uani 0.392(3) 1 d D U P A 2
O1B O 0.3807(6) 0.0337(7) 0.0392(2) 0.1108(16) Uani 0.392(3) 1 d D U P A 2
O2B O 0.3419(6) 0.1577(10) -0.0382(2) 0.158(2) Uani 0.392(3) 1 d D U P A 2
C4B C 0.6302(7) 0.3127(9) 0.0927(2) 0.0423(10) Uani 0.392(3) 1 d D . P A 2
C5B C 0.6695(8) 0.4125(12) 0.0541(4) 0.0555(11) Uani 0.392(3) 1 d D . P A 2
C6B C 0.7617(9) 0.5122(15) 0.0754(6) 0.0885(17) Uani 0.392(3) 1 d D . P A 2
H6BA H 0.7670 0.5927 0.0472 0.133 Uiso 0.392(3) 1 calc R U P A 2
H6BB H 0.8278 0.4534 0.0801 0.133 Uiso 0.392(3) 1 calc R U P A 2
H6BC H 0.7509 0.5559 0.1128 0.133 Uiso 0.392(3) 1 calc R U P A 2
C7B C 0.6221(10) 0.4117(16) -0.0028(4) 0.0896(14) Uani 0.392(3) 1 d D . P A 2
H7BA H 0.6514 0.4743 -0.0296 0.108 Uiso 0.392(3) 1 calc R U P A 2
C8B C 0.5361(10) 0.3268(16) -0.0227(5) 0.1035(16) Uani 0.392(3) 1 d D . P A 2
H8BA H 0.4944 0.3462 -0.0590 0.124 Uiso 0.392(3) 1 calc R U P A 2
C9B C 0.5120(7) 0.2095(12) 0.0129(4) 0.0810(16) Uani 0.392(3) 1 d D . P A 2
C10B C 0.5573(8) 0.2039(13) 0.0707(4) 0.0627(11) Uani 0.392(3) 1 d D . P A 2
H10B H 0.5383 0.1257 0.0951 0.075 Uiso 0.392(3) 1 calc R U P A 2
C11 C 0.5372(2) 0.5205(3) 0.39824(9) 0.0418(7) Uani 1 1 d . . . . .
C12 C 0.4269(2) 0.4949(3) 0.38828(10) 0.0467(7) Uani 1 1 d . . . . .
C13 C 0.3756(3) 0.3851(4) 0.34478(12) 0.0664(9) Uani 1 1 d . . . . .
H13A H 0.3127 0.3413 0.3588 0.100 Uiso 1 1 calc R U . . .
H13B H 0.4265 0.3054 0.3391 0.100 Uiso 1 1 calc R U . . .
H13C H 0.3537 0.4364 0.3079 0.100 Uiso 1 1 calc R U . . .
C14 C 0.3626(2) 0.5745(3) 0.42123(11) 0.0539(8) Uani 1 1 d . . . . .
H14A H 0.2877 0.5587 0.4146 0.065 Uiso 1 1 calc R U . . .
C15 C 0.4030(2) 0.6748(3) 0.46295(11) 0.0518(8) Uani 1 1 d . . . . .
H15A H 0.3573 0.7283 0.4849 0.062 Uiso 1 1 calc R U . . .
C16 C 0.5110(2) 0.6956(3) 0.47205(9) 0.0464(7) Uani 1 1 d D . . . .
C17 C 0.5799(2) 0.6206(3) 0.44071(9) 0.0448(7) Uani 1 1 d . . . . .
H17A H 0.6548 0.6373 0.4481 0.054 Uiso 1 1 calc R U . . .
C18 C 0.3971(2) 0.7970(3) 0.24608(10) 0.0430(7) Uani 1 1 d . . . . .
C19 C 0.4661(2) 0.9069(3) 0.27160(11) 0.0494(7) Uani 1 1 d . . . . .
C20 C 0.5671(2) 0.9509(4) 0.24830(14) 0.0746(10) Uani 1 1 d . . . . .
H20A H 0.5501 0.9799 0.2075 0.112 Uiso 1 1 calc R U . . .
H20B H 0.6165 0.8657 0.2516 0.112 Uiso 1 1 calc R U . . .
H20C H 0.6003 1.0357 0.2707 0.112 Uiso 1 1 calc R U . . .
C21 C 0.4396(2) 0.9767(3) 0.32150(12) 0.0554(8) Uani 1 1 d . . . . .
H21A H 0.4862 1.0507 0.3403 0.066 Uiso 1 1 calc R U . . .
C22 C 0.3478(2) 0.9409(3) 0.34409(11) 0.0527(8) Uani 1 1 d . . . . .
H22A H 0.3311 0.9890 0.3781 0.063 Uiso 1 1 calc R U . . .
C23 C 0.28124(19) 0.8351(3) 0.31675(10) 0.0448(7) Uani 1 1 d D . . . .
C24 C 0.3043(2) 0.7610(3) 0.26802(10) 0.0440(7) Uani 1 1 d . . . . .
H24A H 0.2573 0.6866 0.2499 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.749(3) . ?
S1 C4 1.774(3) . ?
S1 C4B 1.776(5) . ?
S2 C2 1.753(2) . ?
S2 C11 1.776(3) . ?
S3 C3 1.751(3) . ?
S3 C18 1.777(3) . ?
N5 O3 1.213(3) . ?
N5 O4 1.214(3) . ?
N5 C16 1.471(3) . ?
N6 O6 1.210(3) . ?
N6 O5 1.212(2) . ?
N6 C23 1.471(3) . ?
N1 C1 1.327(3) . ?
N1 C3 1.331(3) . ?
N2 C2 1.330(3) . ?
N2 C1 1.337(3) . ?
N3 C2 1.322(3) . ?
N3 C3 1.330(3) . ?
N4 O1 1.210(4) . ?
N4 O2 1.214(4) . ?
N4 C9 1.461(5) . ?
C4 C5 1.395(7) . ?
C4 C10 1.396(7) . ?
C5 C7 1.380(7) . ?
C5 C6 1.497(7) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.341(8) . ?
C7 H7A 0.9500 . ?
C8 C9 1.420(8) . ?
C8 H8A 0.9500 . ?
C9 C10 1.366(7) . ?
C10 H10A 0.9500 . ?
N4B O2B 1.239(4) . ?
N4B O1B 1.244(4) . ?
N4B C9B 1.497(9) . ?
C4B C10B 1.388(10) . ?
C4B C5B 1.404(10) . ?
C5B C7B 1.377(10) . ?
C5B C6B 1.497(11) . ?
C6B H6BA 0.9800 . ?
C6B H6BB 0.9800 . ?
C6B H6BC 0.9800 . ?
C7B C8B 1.353(12) . ?
C7B H7BA 0.9500 . ?
C8B C9B 1.394(12) . ?
C8B H8BA 0.9500 . ?
C9B C10B 1.389(10) . ?
C10B H10B 0.9500 . ?
C11 C17 1.386(3) . ?
C11 C12 1.401(4) . ?
C12 C14 1.386(4) . ?
C12 C13 1.492(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.367(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.366(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.382(4) . ?
C17 H17A 0.9500 . ?
C18 C24 1.379(4) . ?
C18 C19 1.390(4) . ?
C19 C21 1.398(4) . ?
C19 C20 1.505(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.376(4) . ?
C21 H21A 0.9500 . ?
C22 C23 1.363(4) . ?
C22 H22A 0.9500 . ?
C23 C24 1.378(3) . ?
C24 H24A 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
C1 S1 C4 106.2(2) . . ?
C1 S1 C4B 96.9(3) . . ?
C2 S2 C11 104.15(12) . . ?
C3 S3 C18 100.59(11) . . ?
O3 N5 O4 123.8(2) . . ?
O3 N5 C16 118.2(2) . . ?
O4 N5 C16 118.0(2) . . ?
O6 N6 O5 123.6(3) . . ?
O6 N6 C23 118.0(2) . . ?
O5 N6 C23 118.4(2) . . ?
C1 N1 C3 113.0(2) . . ?
C2 N2 C1 113.0(2) . . ?
C2 N3 C3 113.0(2) . . ?
N1 C1 N2 126.7(2) . . ?
N1 C1 S1 121.16(18) . . ?
N2 C1 S1 112.2(2) . . ?
N3 C2 N2 127.1(2) . . ?
N3 C2 S2 120.38(19) . . ?
N2 C2 S2 112.48(19) . . ?
N3 C3 N1 127.1(2) . . ?
N3 C3 S3 118.58(19) . . ?
N1 C3 S3 114.29(17) . . ?
O1 N4 O2 124.5(5) . . ?
O1 N4 C9 112.7(4) . . ?
O2 N4 C9 122.9(5) . . ?
C5 C4 C10 122.9(4) . . ?
C5 C4 S1 115.6(4) . . ?
C10 C4 S1 120.6(4) . . ?
C7 C5 C4 116.7(5) . . ?
C7 C5 C6 120.6(6) . . ?
C4 C5 C6 122.7(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 122.0(7) . . ?
C8 C7 H7A 119.0 . . ?
C5 C7 H7A 119.0 . . ?
C7 C8 C9 119.7(6) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C10 C9 C8 120.3(5) . . ?
C10 C9 N4 124.5(5) . . ?
C8 C9 N4 113.3(5) . . ?
C9 C10 C4 117.1(5) . . ?
C9 C10 H10A 121.5 . . ?
C4 C10 H10A 121.5 . . ?
O2B N4B O1B 116.9(5) . . ?
O2B N4B C9B 118.9(6) . . ?
O1B N4B C9B 123.9(6) . . ?
C10B C4B C5B 118.8(6) . . ?
C10B C4B S1 107.2(6) . . ?
C5B C4B S1 129.6(6) . . ?
C7B C5B C4B 117.9(8) . . ?
C7B C5B C6B 122.7(9) . . ?
C4B C5B C6B 119.4(8) . . ?
C5B C6B H6BA 109.5 . . ?
C5B C6B H6BB 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
C5B C6B H6BC 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C8B C7B C5B 123.8(10) . . ?
C8B C7B H7BA 118.1 . . ?
C5B C7B H7BA 118.1 . . ?
C7B C8B C9B 116.5(10) . . ?
C7B C8B H8BA 121.8 . . ?
C9B C8B H8BA 121.8 . . ?
C10B C9B C8B 120.6(9) . . ?
C10B C9B N4B 109.5(8) . . ?
C8B C9B N4B 123.0(8) . . ?
C4B C10B C9B 119.9(8) . . ?
C4B C10B H10B 120.1 . . ?
C9B C10B H10B 120.1 . . ?
C17 C11 C12 120.4(2) . . ?
C17 C11 S2 115.9(2) . . ?
C12 C11 S2 123.1(2) . . ?
C14 C12 C11 118.0(2) . . ?
C14 C12 C13 118.5(3) . . ?
C11 C12 C13 123.4(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C12 122.5(3) . . ?
C15 C14 H14A 118.7 . . ?
C12 C14 H14A 118.7 . . ?
C16 C15 C14 117.9(3) . . ?
C16 C15 H15A 121.1 . . ?
C14 C15 H15A 121.1 . . ?
C15 C16 C17 122.8(2) . . ?
C15 C16 N5 118.6(2) . . ?
C17 C16 N5 118.6(2) . . ?
C16 C17 C11 118.4(2) . . ?
C16 C17 H17A 120.8 . . ?
C11 C17 H17A 120.8 . . ?
C24 C18 C19 121.5(2) . . ?
C24 C18 S3 118.0(2) . . ?
C19 C18 S3 120.6(2) . . ?
C18 C19 C21 117.5(3) . . ?
C18 C19 C20 122.9(3) . . ?
C21 C19 C20 119.6(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C19 121.6(3) . . ?
C22 C21 H21A 119.2 . . ?
C19 C21 H21A 119.2 . . ?
C23 C22 C21 118.8(2) . . ?
C23 C22 H22A 120.6 . . ?
C21 C22 H22A 120.6 . . ?
C22 C23 C24 122.0(2) . . ?
C22 C23 N6 119.0(2) . . ?
C24 C23 N6 119.0(2) . . ?
C23 C24 C18 118.6(2) . . ?
C23 C24 H24A 120.7 . . ?
C18 C24 H24A 120.7 . . ?

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
C3 N1 C1 N2 -1.3(4) . . . . ?
C3 N1 C1 S1 177.8(2) . . . . ?
C2 N2 C1 N1 1.0(4) . . . . ?
C2 N2 C1 S1 -178.1(2) . . . . ?
C4 S1 C1 N1 -8.2(3) . . . . ?
C4B S1 C1 N1 -3.1(4) . . . . ?
C4 S1 C1 N2 171.0(3) . . . . ?
C4B S1 C1 N2 176.1(3) . . . . ?
C3 N3 C2 N2 0.4(4) . . . . ?
C3 N3 C2 S2 -178.55(19) . . . . ?
C1 N2 C2 N3 -0.5(4) . . . . ?
C1 N2 C2 S2 178.48(19) . . . . ?
C11 S2 C2 N3 10.3(3) . . . . ?
C11 S2 C2 N2 -168.8(2) . . . . ?
C2 N3 C3 N1 -0.7(4) . . . . ?
C2 N3 C3 S3 176.7(2) . . . . ?
C1 N1 C3 N3 1.1(4) . . . . ?
C1 N1 C3 S3 -176.4(2) . . . . ?
C18 S3 C3 N3 7.8(2) . . . . ?
C18 S3 C3 N1 -174.5(2) . . . . ?
C1 S1 C4 C5 86.7(5) . . . . ?
C1 S1 C4 C10 -82.8(5) . . . . ?
C10 C4 C5 C7 -10.1(10) . . . . ?
S1 C4 C5 C7 -179.3(6) . . . . ?
C10 C4 C5 C6 167.9(7) . . . . ?
S1 C4 C5 C6 -1.3(9) . . . . ?
C4 C5 C7 C8 1.9(13) . . . . ?
C6 C5 C7 C8 -176.1(9) . . . . ?
C5 C7 C8 C9 7.9(15) . . . . ?
C7 C8 C9 C10 -10.4(13) . . . . ?
C7 C8 C9 N4 -175.3(8) . . . . ?
O1 N4 C9 C10 15.2(9) . . . . ?
O2 N4 C9 C10 -165.4(7) . . . . ?
O1 N4 C9 C8 179.4(7) . . . . ?
O2 N4 C9 C8 -1.2(10) . . . . ?
C8 C9 C10 C4 2.7(10) . . . . ?
N4 C9 C10 C4 165.8(6) . . . . ?
C5 C4 C10 C9 7.6(10) . . . . ?
S1 C4 C10 C9 176.3(5) . . . . ?
C1 S1 C4B C10B -107.9(7) . . . . ?
C1 S1 C4B C5B 96.7(9) . . . . ?
C10B C4B C5B C7B 9.4(16) . . . . ?
S1 C4B C5B C7B 162.4(10) . . . . ?
C10B C4B C5B C6B -169.2(11) . . . . ?
S1 C4B C5B C6B -16.2(16) . . . . ?
C4B C5B C7B C8B 4(2) . . . . ?
C6B C5B C7B C8B -177.4(14) . . . . ?
C5B C7B C8B C9B -16(2) . . . . ?
C7B C8B C9B C10B 15(2) . . . . ?
C7B C8B C9B N4B 162.9(12) . . . . ?
O2B N4B C9B C10B 161.9(10) . . . . ?
O1B N4B C9B C10B -24.8(14) . . . . ?
O2B N4B C9B C8B 11.0(16) . . . . ?
O1B N4B C9B C8B -175.7(11) . . . . ?
C5B C4B C10B C9B -10.0(16) . . . . ?
S1 C4B C10B C9B -168.5(9) . . . . ?
C8B C9B C10B C4B -2.4(17) . . . . ?
N4B C9B C10B C4B -154.1(10) . . . . ?
C2 S2 C11 C17 -124.2(2) . . . . ?
C2 S2 C11 C12 65.0(2) . . . . ?
C17 C11 C12 C14 1.2(4) . . . . ?
S2 C11 C12 C14 171.6(2) . . . . ?
C17 C11 C12 C13 -177.8(2) . . . . ?
S2 C11 C12 C13 -7.5(4) . . . . ?
C11 C12 C14 C15 -0.6(4) . . . . ?
C13 C12 C14 C15 178.5(3) . . . . ?
C12 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C14 C15 C16 N5 -177.0(2) . . . . ?
O3 N5 C16 C15 174.1(3) . . . . ?
O4 N5 C16 C15 -3.4(4) . . . . ?
O3 N5 C16 C17 -3.5(4) . . . . ?
O4 N5 C16 C17 179.1(3) . . . . ?
C15 C16 C17 C11 0.2(4) . . . . ?
N5 C16 C17 C11 177.6(2) . . . . ?
C12 C11 C17 C16 -1.0(4) . . . . ?
S2 C11 C17 C16 -172.05(19) . . . . ?
C3 S3 C18 C24 -99.8(2) . . . . ?
C3 S3 C18 C19 80.4(2) . . . . ?
C24 C18 C19 C21 1.8(4) . . . . ?
S3 C18 C19 C21 -178.4(2) . . . . ?
C24 C18 C19 C20 -179.0(3) . . . . ?
S3 C18 C19 C20 0.8(4) . . . . ?
C18 C19 C21 C22 -1.3(4) . . . . ?
C20 C19 C21 C22 179.5(3) . . . . ?
C19 C21 C22 C23 -0.3(4) . . . . ?
C21 C22 C23 C24 1.4(4) . . . . ?
C21 C22 C23 N6 179.2(2) . . . . ?
O6 N6 C23 C22 172.4(3) . . . . ?
O5 N6 C23 C22 -7.5(4) . . . . ?
O6 N6 C23 C24 -9.8(4) . . . . ?
O5 N6 C23 C24 170.3(3) . . . . ?
C22 C23 C24 C18 -0.9(4) . . . . ?
N6 C23 C24 C18 -178.6(2) . . . . ?
C19 C18 C24 C23 -0.8(4) . . . . ?
S3 C18 C24 C23 179.39(19) . . . . ?

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
C8 H8A S3 0.95 2.96 3.801(8) 148.6 3_665

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1436791'
_audit_update_record             
;
2015-11-13 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 N3 S3, 0.5(C6 F6)'
_chemical_formula_sum            'C30 H27 F3 N3 S3'
_chemical_formula_weight         582.72

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'
F F 0.0171 0.0103 '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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.411(2)
_cell_length_b                   12.295(3)
_cell_length_c                   13.934(3)
_cell_angle_alpha                108.662(4)
_cell_angle_beta                 108.819(3)
_cell_angle_gamma                92.389(4)
_cell_volume                     1426.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4013
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      28.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             606
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.304
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.573
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8482
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.771
_diffrn_reflns_theta_max         28.254
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             6145
_reflns_number_gt                5033
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6145
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0930
_refine_ls_wR_factor_ref         0.2863
_refine_ls_wR_factor_gt          0.2450
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.163
_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_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 0.90396(10) 0.32122(7) 0.55233(6) 0.0251(3) Uani 1 1 d . . . . .
S2 S 0.97290(9) 0.12037(7) 0.83557(6) 0.0234(3) Uani 1 1 d . . . . .
S3 S 0.63369(9) 0.45940(7) 0.83742(6) 0.0242(3) Uani 1 1 d . . . . .
F1 F 0.2961(3) -0.0096(2) 0.6017(2) 0.0527(7) Uani 1 1 d . . . . .
F2 F 0.0746(3) -0.0976(2) 0.65567(17) 0.0480(7) Uani 1 1 d . . . . .
F3 F -0.2218(3) -0.0875(2) 0.5532(3) 0.0547(7) Uani 1 1 d . . . . .
N1 N 0.9221(3) 0.2304(2) 0.6998(2) 0.0207(6) Uani 1 1 d . . . . .
N2 N 0.8026(3) 0.2891(2) 0.83132(19) 0.0201(6) Uani 1 1 d . . . . .
N3 N 0.7738(3) 0.3842(2) 0.7024(2) 0.0206(6) Uani 1 1 d . . . . .
C1 C 0.8600(3) 0.3132(3) 0.6630(2) 0.0200(6) Uani 1 1 d . . . . .
C2 C 0.8884(3) 0.2249(3) 0.7850(2) 0.0190(6) Uani 1 1 d . . . . .
C3 C 0.7487(3) 0.3668(3) 0.7862(2) 0.0192(6) Uani 1 1 d . . . . .
C4 C 0.7986(4) 0.4290(3) 0.5177(3) 0.0246(7) Uani 1 1 d . . . . .
C5 C 0.8623(4) 0.5467(3) 0.5714(3) 0.0268(7) Uani 1 1 d . . . . .
C6 C 0.7799(5) 0.6287(3) 0.5388(3) 0.0327(8) Uani 1 1 d . . . . .
H6A H 0.8199 0.7092 0.5747 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6398(5) 0.5934(4) 0.4544(3) 0.0382(9) Uani 1 1 d . . . . .
H7A H 0.5855 0.6499 0.4325 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5798(4) 0.4775(4) 0.4026(3) 0.0363(9) Uani 1 1 d . . . . .
H8A H 0.4834 0.4548 0.3457 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6576(4) 0.3924(3) 0.4321(3) 0.0313(8) Uani 1 1 d . . . . .
C10 C 1.0121(4) 0.5868(3) 0.6638(3) 0.0319(8) Uani 1 1 d . . . . .
H10A H 1.0525 0.6662 0.6742 0.048 Uiso 1 1 calc R U . . .
H10B H 1.0840 0.5349 0.6474 0.048 Uiso 1 1 calc R U . . .
H10C H 0.9977 0.5856 0.7300 0.048 Uiso 1 1 calc R U . . .
C11 C 0.5876(5) 0.2663(4) 0.3732(4) 0.0449(10) Uani 1 1 d . . . . .
H11A H 0.6575 0.2237 0.3422 0.067 Uiso 1 1 calc R U . . .
H11B H 0.4915 0.2597 0.3150 0.067 Uiso 1 1 calc R U . . .
H11C H 0.5681 0.2334 0.4240 0.067 Uiso 1 1 calc R U . . .
C12 C 0.8879(4) 0.1156(3) 0.9312(3) 0.0217(6) Uani 1 1 d . . . . .
C13 C 0.9805(4) 0.1552(3) 1.0416(3) 0.0235(7) Uani 1 1 d . . . . .
C14 C 0.9180(4) 0.1358(3) 1.1143(3) 0.0282(7) Uani 1 1 d . . . . .
H14A H 0.9793 0.1593 1.1888 0.034 Uiso 1 1 calc R U . . .
C15 C 0.7690(5) 0.0830(3) 1.0799(3) 0.0342(8) Uani 1 1 d . . . . .
H15A H 0.7291 0.0703 1.1306 0.041 Uiso 1 1 calc R U . . .
C16 C 0.6780(5) 0.0488(3) 0.9723(3) 0.0351(8) Uani 1 1 d . . . . .
H16A H 0.5746 0.0152 0.9499 0.042 Uiso 1 1 calc R U . . .
C17 C 0.7356(4) 0.0629(3) 0.8954(3) 0.0266(7) Uani 1 1 d . . . . .
C18 C 1.1416(4) 0.2167(4) 1.0831(3) 0.0344(8) Uani 1 1 d . . . . .
H18A H 1.1429 0.2858 1.0625 0.052 Uiso 1 1 calc R U . . .
H18B H 1.2033 0.1642 1.0516 0.052 Uiso 1 1 calc R U . . .
H18C H 1.1836 0.2403 1.1623 0.052 Uiso 1 1 calc R U . . .
C19 C 0.6339(5) 0.0232(4) 0.7784(3) 0.0414(10) Uani 1 1 d . . . . .
H19A H 0.5356 -0.0169 0.7693 0.062 Uiso 1 1 calc R U . . .
H19B H 0.6815 -0.0302 0.7339 0.062 Uiso 1 1 calc R U . . .
H19C H 0.6181 0.0907 0.7556 0.062 Uiso 1 1 calc R U . . .
C20 C 0.5897(4) 0.3939(3) 0.9232(2) 0.0213(6) Uani 1 1 d . . . . .
C21 C 0.6880(4) 0.4230(3) 1.0307(3) 0.0252(7) Uani 1 1 d . . . . .
C22 C 0.6445(4) 0.3743(3) 1.0964(3) 0.0254(7) Uani 1 1 d . . . . .
H22A H 0.7085 0.3933 1.1698 0.030 Uiso 1 1 calc R U . . .
C23 C 0.5085(4) 0.2984(3) 1.0558(3) 0.0297(8) Uani 1 1 d . . . . .
H23A H 0.4809 0.2656 1.1017 0.036 Uiso 1 1 calc R U . . .
C24 C 0.4127(4) 0.2699(3) 0.9496(3) 0.0295(7) Uani 1 1 d . . . . .
H24A H 0.3201 0.2176 0.9231 0.035 Uiso 1 1 calc R U . . .
C25 C 0.4508(4) 0.3172(3) 0.8810(3) 0.0261(7) Uani 1 1 d . . . . .
C26 C 0.8382(4) 0.5025(3) 1.0747(3) 0.0291(7) Uani 1 1 d . . . . .
H26A H 0.8795 0.5258 1.1538 0.044 Uiso 1 1 calc R U . . .
H26B H 0.8230 0.5718 1.0547 0.044 Uiso 1 1 calc R U . . .
H26C H 0.9096 0.4616 1.0442 0.044 Uiso 1 1 calc R U . . .
C27 C 0.3441(4) 0.2854(3) 0.7655(3) 0.0342(8) Uani 1 1 d . . . . .
H27A H 0.2545 0.2317 0.7527 0.051 Uiso 1 1 calc R U . . .
H27B H 0.3963 0.2479 0.7161 0.051 Uiso 1 1 calc R U . . .
H27C H 0.3124 0.3559 0.7526 0.051 Uiso 1 1 calc R U . . .
C28 C 0.1495(4) -0.0047(3) 0.5519(3) 0.0343(8) Uani 1 1 d . . . . .
C29 C 0.0381(5) -0.0493(3) 0.5791(3) 0.0328(9) Uani 1 1 d . . . . .
C30 C -0.1123(4) -0.0446(3) 0.5277(3) 0.0321(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.751(3) . ?
S1 C4 1.784(3) . ?
S2 C2 1.757(3) . ?
S2 C12 1.776(3) . ?
S3 C3 1.749(3) . ?
S3 C20 1.777(3) . ?
F1 C28 1.343(4) . ?
F2 C29 1.340(4) . ?
F3 C30 1.334(4) . ?
N1 C2 1.344(4) . ?
N1 C1 1.353(4) . ?
N2 C2 1.325(4) . ?
N2 C3 1.335(3) . ?
N3 C1 1.326(4) . ?
N3 C3 1.341(4) . ?
C4 C5 1.400(5) . ?
C4 C9 1.404(5) . ?
C5 C6 1.398(4) . ?
C5 C10 1.501(5) . ?
C6 C7 1.391(6) . ?
C6 H6A 0.9500 . ?
C7 C8 1.372(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.394(5) . ?
C8 H8A 0.9500 . ?
C9 C11 1.505(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.407(5) . ?
C12 C13 1.408(4) . ?
C13 C14 1.397(5) . ?
C13 C18 1.506(5) . ?
C14 C15 1.382(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.377(6) . ?
C15 H15A 0.9500 . ?
C16 C17 1.399(5) . ?
C16 H16A 0.9500 . ?
C17 C19 1.502(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.401(4) . ?
C20 C25 1.411(5) . ?
C21 C22 1.391(4) . ?
C21 C26 1.507(5) . ?
C22 C23 1.387(5) . ?
C22 H22A 0.9500 . ?
C23 C24 1.381(5) . ?
C23 H23A 0.9500 . ?
C24 C25 1.392(5) . ?
C24 H24A 0.9500 . ?
C25 C27 1.508(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.372(6) . ?
C28 C30 1.385(5) 2_556 ?
C29 C30 1.378(5) . ?
C30 C28 1.385(5) 2_556 ?

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 C4 102.66(15) . . ?
C2 S2 C12 103.74(14) . . ?
C3 S3 C20 101.66(14) . . ?
C2 N1 C1 112.8(3) . . ?
C2 N2 C3 113.6(3) . . ?
C1 N3 C3 113.4(2) . . ?
N3 C1 N1 126.6(3) . . ?
N3 C1 S1 120.3(2) . . ?
N1 C1 S1 113.1(2) . . ?
N2 C2 N1 126.8(3) . . ?
N2 C2 S2 120.0(2) . . ?
N1 C2 S2 113.2(2) . . ?
N2 C3 N3 126.7(3) . . ?
N2 C3 S3 119.9(2) . . ?
N3 C3 S3 113.4(2) . . ?
C5 C4 C9 121.8(3) . . ?
C5 C4 S1 119.5(3) . . ?
C9 C4 S1 118.6(3) . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 C10 119.7(3) . . ?
C4 C5 C10 122.3(3) . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
C8 C9 C4 118.0(3) . . ?
C8 C9 C11 119.5(3) . . ?
C4 C9 C11 122.6(3) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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 . . ?
C17 C12 C13 121.3(3) . . ?
C17 C12 S2 120.0(2) . . ?
C13 C12 S2 118.4(3) . . ?
C14 C13 C12 117.8(3) . . ?
C14 C13 C18 119.6(3) . . ?
C12 C13 C18 122.6(3) . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 120.9(4) . . ?
C15 C16 H16A 119.5 . . ?
C17 C16 H16A 119.5 . . ?
C16 C17 C12 118.3(3) . . ?
C16 C17 C19 119.6(3) . . ?
C12 C17 C19 122.1(3) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 121.9(3) . . ?
C21 C20 S3 120.1(3) . . ?
C25 C20 S3 117.9(2) . . ?
C22 C21 C20 117.9(3) . . ?
C22 C21 C26 120.3(3) . . ?
C20 C21 C26 121.8(3) . . ?
C23 C22 C21 120.7(3) . . ?
C23 C22 H22A 119.7 . . ?
C21 C22 H22A 119.7 . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23A 119.5 . . ?
C22 C23 H23A 119.5 . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 H24A 119.8 . . ?
C25 C24 H24A 119.8 . . ?
C24 C25 C20 118.1(3) . . ?
C24 C25 C27 119.6(3) . . ?
C20 C25 C27 122.3(3) . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
F1 C28 C29 120.2(3) . . ?
F1 C28 C30 119.2(4) . 2_556 ?
C29 C28 C30 120.6(3) . 2_556 ?
F2 C29 C28 120.4(4) . . ?
F2 C29 C30 119.6(4) . . ?
C28 C29 C30 120.1(3) . . ?
F3 C30 C29 120.8(3) . . ?
F3 C30 C28 119.9(4) . 2_556 ?
C29 C30 C28 119.3(4) . 2_556 ?

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
C3 N3 C1 N1 -0.7(5) . . . . ?
C3 N3 C1 S1 179.3(2) . . . . ?
C2 N1 C1 N3 -0.2(5) . . . . ?
C2 N1 C1 S1 179.8(2) . . . . ?
C4 S1 C1 N3 -3.5(3) . . . . ?
C4 S1 C1 N1 176.5(2) . . . . ?
C3 N2 C2 N1 -0.9(5) . . . . ?
C3 N2 C2 S2 178.5(2) . . . . ?
C1 N1 C2 N2 1.1(5) . . . . ?
C1 N1 C2 S2 -178.3(2) . . . . ?
C12 S2 C2 N2 9.2(3) . . . . ?
C12 S2 C2 N1 -171.4(2) . . . . ?
C2 N2 C3 N3 -0.3(5) . . . . ?
C2 N2 C3 S3 -179.8(2) . . . . ?
C1 N3 C3 N2 1.0(5) . . . . ?
C1 N3 C3 S3 -179.5(2) . . . . ?
C20 S3 C3 N2 -12.7(3) . . . . ?
C20 S3 C3 N3 167.7(2) . . . . ?
C1 S1 C4 C5 85.4(3) . . . . ?
C1 S1 C4 C9 -98.6(3) . . . . ?
C9 C4 C5 C6 1.2(5) . . . . ?
S1 C4 C5 C6 177.0(3) . . . . ?
C9 C4 C5 C10 179.3(3) . . . . ?
S1 C4 C5 C10 -4.9(5) . . . . ?
C4 C5 C6 C7 -0.9(5) . . . . ?
C10 C5 C6 C7 -179.1(3) . . . . ?
C5 C6 C7 C8 0.7(6) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C7 C8 C9 C4 1.0(6) . . . . ?
C7 C8 C9 C11 180.0(4) . . . . ?
C5 C4 C9 C8 -1.2(5) . . . . ?
S1 C4 C9 C8 -177.1(3) . . . . ?
C5 C4 C9 C11 179.8(4) . . . . ?
S1 C4 C9 C11 4.0(5) . . . . ?
C2 S2 C12 C17 72.8(3) . . . . ?
C2 S2 C12 C13 -113.2(2) . . . . ?
C17 C12 C13 C14 2.8(4) . . . . ?
S2 C12 C13 C14 -171.0(2) . . . . ?
C17 C12 C13 C18 -177.1(3) . . . . ?
S2 C12 C13 C18 9.0(4) . . . . ?
C12 C13 C14 C15 -2.1(4) . . . . ?
C18 C13 C14 C15 177.8(3) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C17 2.2(5) . . . . ?
C15 C16 C17 C12 -1.5(5) . . . . ?
C15 C16 C17 C19 179.1(4) . . . . ?
C13 C12 C17 C16 -1.1(5) . . . . ?
S2 C12 C17 C16 172.7(3) . . . . ?
C13 C12 C17 C19 178.3(3) . . . . ?
S2 C12 C17 C19 -8.0(4) . . . . ?
C3 S3 C20 C21 86.7(3) . . . . ?
C3 S3 C20 C25 -96.3(3) . . . . ?
C25 C20 C21 C22 -0.4(5) . . . . ?
S3 C20 C21 C22 176.5(2) . . . . ?
C25 C20 C21 C26 178.4(3) . . . . ?
S3 C20 C21 C26 -4.7(4) . . . . ?
C20 C21 C22 C23 0.7(5) . . . . ?
C26 C21 C22 C23 -178.1(3) . . . . ?
C21 C22 C23 C24 -0.4(5) . . . . ?
C22 C23 C24 C25 -0.1(5) . . . . ?
C23 C24 C25 C20 0.4(5) . . . . ?
C23 C24 C25 C27 -179.7(3) . . . . ?
C21 C20 C25 C24 -0.1(5) . . . . ?
S3 C20 C25 C24 -177.1(2) . . . . ?
C21 C20 C25 C27 179.9(3) . . . . ?
S3 C20 C25 C27 3.0(4) . . . . ?
F1 C28 C29 F2 0.2(5) . . . . ?
C30 C28 C29 F2 179.6(3) 2_556 . . . ?
F1 C28 C29 C30 -179.8(3) . . . . ?
C30 C28 C29 C30 -0.5(6) 2_556 . . . ?
F2 C29 C30 F3 0.0(5) . . . . ?
C28 C29 C30 F3 180.0(3) . . . . ?
F2 C29 C30 C28 -179.6(3) . . . 2_556 ?
C28 C29 C30 C28 0.5(6) . . . 2_556 ?

_refine_diff_density_max         1.346
_refine_diff_density_min         -1.416
_refine_diff_density_rms         0.163

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1436792'
_audit_update_record             
;
2015-11-13 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 N3 S3'
_chemical_formula_sum            'C27 H27 N3 S3'
_chemical_formula_weight         489.69

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_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                   11.446(2)
_cell_length_b                   9.9569(18)
_cell_length_c                   22.647(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.964(8)
_cell_angle_gamma                90
_cell_volume                     2574.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6006
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.66

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.308
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6065
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20447
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         25.252
_diffrn_reflns_theta_full        25.252
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4651
_reflns_number_gt                3005
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+1.2268P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0082(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4651
_refine_ls_number_parameters     312
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.019
_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_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 0.45265(7) 0.60050(8) 0.38157(3) 0.0577(3) Uani 1 1 d . . . . .
S2 S 0.44287(7) 0.70470(9) 0.15414(3) 0.0613(3) Uani 1 1 d . . . . .
S3 S 0.81159(8) 0.83540(11) 0.28636(4) 0.0857(4) Uani 1 1 d . . . . .
N1 N 0.45829(18) 0.6592(2) 0.27074(9) 0.0470(6) Uani 1 1 d . . . . .
N2 N 0.6199(2) 0.7606(3) 0.22740(9) 0.0566(7) Uani 1 1 d . . . . .
N3 N 0.62899(19) 0.7172(2) 0.33092(9) 0.0481(6) Uani 1 1 d . . . . .
C1 C 0.5224(2) 0.6661(3) 0.32212(11) 0.0434(7) Uani 1 1 d . . . . .
C2 C 0.5125(2) 0.7081(3) 0.22550(11) 0.0477(7) Uani 1 1 d . . . . .
C3 C 0.6721(2) 0.7625(3) 0.28183(12) 0.0527(7) Uani 1 1 d . . . . .
C4 C 0.5553(8) 0.5956(12) 0.4408(4) 0.0428(19) Uani 0.574(7) 1 d DG U P A 1
C5 C 0.5505(6) 0.6938(10) 0.4842(5) 0.0498(17) Uani 0.574(7) 1 d DG U P A 1
C6 C 0.6360(7) 0.6984(8) 0.5308(4) 0.061(2) Uani 0.574(7) 1 d DG U P A 1
H6A H 0.6327 0.7654 0.5605 0.074 Uiso 0.574(7) 1 calc R U P A 1
C7 C 0.7264(7) 0.6048(8) 0.5340(4) 0.061(2) Uani 0.574(7) 1 d DG U P A 1
H7A H 0.7849 0.6080 0.5659 0.074 Uiso 0.574(7) 1 calc R U P A 1
C8 C 0.7312(9) 0.5067(9) 0.4906(5) 0.0660(17) Uani 0.574(7) 1 d DG U P A 1
H8A H 0.7930 0.4428 0.4928 0.079 Uiso 0.574(7) 1 calc R U P A 1
C9 C 0.6457(10) 0.5021(12) 0.4440(5) 0.0573(13) Uani 0.574(7) 1 d DG U P A 1
C10 C 0.4581(8) 0.8014(12) 0.4837(8) 0.078(3) Uani 0.574(7) 1 d D U P A 1
H10A H 0.4592 0.8437 0.5228 0.117 Uiso 0.574(7) 1 calc R U P A 1
H10B H 0.3810 0.7612 0.4739 0.117 Uiso 0.574(7) 1 calc R U P A 1
H10C H 0.4739 0.8693 0.4539 0.117 Uiso 0.574(7) 1 calc R U P A 1
C11 C 0.652(3) 0.396(3) 0.3963(10) 0.088(2) Uani 0.574(7) 1 d D U P A 1
H11A H 0.7012 0.3217 0.4115 0.131 Uiso 0.574(7) 1 calc R U P A 1
H11B H 0.6860 0.4357 0.3617 0.131 Uiso 0.574(7) 1 calc R U P A 1
H11C H 0.5731 0.3632 0.3849 0.131 Uiso 0.574(7) 1 calc R U P A 1
C4A C 0.5796(12) 0.6021(17) 0.4353(6) 0.0428(19) Uani 0.426(7) 1 d DG . P A 2
C5A C 0.5874(10) 0.6896(13) 0.4832(7) 0.0498(17) Uani 0.426(7) 1 d DG . P A 2
C6A C 0.6680(11) 0.6654(11) 0.5308(6) 0.061(2) Uani 0.426(7) 1 d DG . P A 2
H6AA H 0.6734 0.7253 0.5635 0.074 Uiso 0.426(7) 1 calc R U P A 2
C7A C 0.7408(11) 0.5537(10) 0.5304(6) 0.061(2) Uani 0.426(7) 1 d DG . P A 2
H7AA H 0.7959 0.5372 0.5629 0.074 Uiso 0.426(7) 1 calc R U P A 2
C8A C 0.7330(13) 0.4662(12) 0.4825(7) 0.0660(17) Uani 0.426(7) 1 d DG . P A 2
H8AA H 0.7827 0.3899 0.4822 0.079 Uiso 0.426(7) 1 calc R U P A 2
C9A C 0.6523(15) 0.4904(17) 0.4349(7) 0.0573(13) Uani 0.426(7) 1 d DG . P A 2
C10A C 0.5062(12) 0.8089(17) 0.4834(11) 0.078(3) Uani 0.426(7) 1 d D . P A 2
H10D H 0.5212 0.8593 0.5203 0.117 Uiso 0.426(7) 1 calc R U P A 2
H10E H 0.4248 0.7777 0.4803 0.117 Uiso 0.426(7) 1 calc R U P A 2
H10F H 0.5198 0.8673 0.4497 0.117 Uiso 0.426(7) 1 calc R U P A 2
C11A C 0.652(4) 0.391(4) 0.3850(14) 0.088(2) Uani 0.426(7) 1 d D . P A 2
H11D H 0.7272 0.3433 0.3868 0.131 Uiso 0.426(7) 1 calc R U P A 2
H11E H 0.6407 0.4386 0.3472 0.131 Uiso 0.426(7) 1 calc R U P A 2
H11F H 0.5885 0.3264 0.3886 0.131 Uiso 0.426(7) 1 calc R U P A 2
C12 C 0.2992(6) 0.6615(11) 0.1690(9) 0.0468(16) Uani 0.574(7) 1 d DG U P A 1
C13 C 0.2354(8) 0.7677(9) 0.1903(8) 0.0549(14) Uani 0.574(7) 1 d DG U P A 1
C14 C 0.1156(7) 0.7543(7) 0.1953(5) 0.0604(19) Uani 0.574(7) 1 d DG U P A 1
H14A H 0.0720 0.8269 0.2098 0.072 Uiso 0.574(7) 1 calc R U P A 1
C15 C 0.0596(6) 0.6348(7) 0.1789(4) 0.058(2) Uani 0.574(7) 1 d DG U P A 1
H15A H -0.0223 0.6257 0.1823 0.069 Uiso 0.574(7) 1 calc R U P A 1
C16 C 0.1233(7) 0.5286(7) 0.1577(6) 0.0614(18) Uani 0.574(7) 1 d DG U P A 1
H16A H 0.0851 0.4469 0.1465 0.074 Uiso 0.574(7) 1 calc R U P A 1
C17 C 0.2432(7) 0.5419(10) 0.1527(8) 0.0552(15) Uani 0.574(7) 1 d DG U P A 1
C18 C 0.2852(13) 0.9089(13) 0.2017(7) 0.067(3) Uani 0.574(7) 1 d D U P A 1
H18A H 0.2244 0.9669 0.2164 0.101 Uiso 0.574(7) 1 calc R U P A 1
H18B H 0.3112 0.9459 0.1647 0.101 Uiso 0.574(7) 1 calc R U P A 1
H18C H 0.3518 0.9042 0.2312 0.101 Uiso 0.574(7) 1 calc R U P A 1
C19 C 0.3110(11) 0.4281(17) 0.1269(11) 0.082(3) Uani 0.574(7) 1 d D U P A 1
H19A H 0.2562 0.3649 0.1066 0.123 Uiso 0.574(7) 1 calc R U P A 1
H19B H 0.3568 0.3813 0.1587 0.123 Uiso 0.574(7) 1 calc R U P A 1
H19C H 0.3638 0.4643 0.0986 0.123 Uiso 0.574(7) 1 calc R U P A 1
C12A C 0.2943(10) 0.6700(15) 0.1624(12) 0.0468(16) Uani 0.426(7) 1 d DG . P A 2
C13A C 0.2126(11) 0.7544(12) 0.1858(11) 0.0549(14) Uani 0.426(7) 1 d DG . P A 2
C14A C 0.0994(11) 0.7089(10) 0.1923(8) 0.0604(19) Uani 0.426(7) 1 d DG . P A 2
H14B H 0.0436 0.7666 0.2083 0.072 Uiso 0.426(7) 1 calc R U P A 2
C15A C 0.0679(9) 0.5790(9) 0.1753(6) 0.058(2) Uani 0.426(7) 1 d DG . P A 2
H15B H -0.0094 0.5479 0.1797 0.069 Uiso 0.426(7) 1 calc R U P A 2
C16A C 0.1496(10) 0.4946(10) 0.1518(8) 0.0614(18) Uani 0.426(7) 1 d DG . P A 2
H16B H 0.1281 0.4058 0.1402 0.074 Uiso 0.426(7) 1 calc R U P A 2
C17A C 0.2629(10) 0.5401(14) 0.1454(11) 0.0552(15) Uani 0.426(7) 1 d DG . P A 2
C18A C 0.2525(18) 0.8898(18) 0.2115(11) 0.067(3) Uani 0.426(7) 1 d D . P A 2
H18D H 0.3136 0.8757 0.2433 0.101 Uiso 0.426(7) 1 calc R U P A 2
H18E H 0.1858 0.9361 0.2272 0.101 Uiso 0.426(7) 1 calc R U P A 2
H18F H 0.2838 0.9447 0.1803 0.101 Uiso 0.426(7) 1 calc R U P A 2
C19A C 0.3493(16) 0.433(2) 0.1300(16) 0.082(3) Uani 0.426(7) 1 d D . P A 2
H19D H 0.3165 0.3445 0.1372 0.123 Uiso 0.426(7) 1 calc R U P A 2
H19E H 0.4224 0.4450 0.1547 0.123 Uiso 0.426(7) 1 calc R U P A 2
H19F H 0.3652 0.4416 0.0882 0.123 Uiso 0.426(7) 1 calc R U P A 2
C20 C 0.8532(15) 0.8115(13) 0.3629(3) 0.0497(14) Uani 0.574(7) 1 d DG U P A 1
C21 C 0.8425(11) 0.9004(10) 0.4095(3) 0.0608(15) Uani 0.574(7) 1 d DG U P A 1
C22 C 0.8965(8) 0.8720(7) 0.4649(3) 0.072(2) Uani 0.574(7) 1 d DG U P A 1
H22A H 0.8892 0.9327 0.4968 0.086 Uiso 0.574(7) 1 calc R U P A 1
C23 C 0.9613(7) 0.7547(8) 0.4737(2) 0.074(2) Uani 0.574(7) 1 d DG U P A 1
H23A H 0.9982 0.7353 0.5116 0.088 Uiso 0.574(7) 1 calc R U P A 1
C24 C 0.9720(10) 0.6658(8) 0.4271(3) 0.074(2) Uani 0.574(7) 1 d DG U P A 1
H24A H 1.0163 0.5857 0.4331 0.089 Uiso 0.574(7) 1 calc R U P A 1
C25 C 0.9179(14) 0.6942(12) 0.3717(3) 0.0604(14) Uani 0.574(7) 1 d DG U P A 1
C26 C 0.7703(16) 1.0266(14) 0.4000(5) 0.101(3) Uani 0.574(7) 1 d D U P A 1
H26A H 0.7741 1.0794 0.4366 0.152 Uiso 0.574(7) 1 calc R U P A 1
H26B H 0.6887 1.0024 0.3890 0.152 Uiso 0.574(7) 1 calc R U P A 1
H26C H 0.8012 1.0799 0.3682 0.152 Uiso 0.574(7) 1 calc R U P A 1
C27 C 0.9303(18) 0.5873(18) 0.3250(7) 0.105(4) Uani 0.574(7) 1 d D U P A 1
H27A H 0.9723 0.5099 0.3427 0.157 Uiso 0.574(7) 1 calc R U P A 1
H27B H 0.9743 0.6238 0.2930 0.157 Uiso 0.574(7) 1 calc R U P A 1
H27C H 0.8524 0.5591 0.3090 0.157 Uiso 0.574(7) 1 calc R U P A 1
C20A C 0.866(2) 0.8060(19) 0.3578(4) 0.0497(14) Uani 0.426(7) 1 d DG . P A 2
C21A C 0.8353(16) 0.9141(14) 0.3924(5) 0.0608(15) Uani 0.426(7) 1 d DG . P A 2
C22A C 0.8697(10) 0.9165(9) 0.4525(4) 0.072(2) Uani 0.426(7) 1 d DG . P A 2
H22B H 0.8488 0.9904 0.4761 0.086 Uiso 0.426(7) 1 calc R U P A 2
C23A C 0.9348(10) 0.8110(10) 0.4779(3) 0.074(2) Uani 0.426(7) 1 d DG . P A 2
H23B H 0.9583 0.8127 0.5190 0.088 Uiso 0.426(7) 1 calc R U P A 2
C24A C 0.9654(14) 0.7030(11) 0.4433(5) 0.074(2) Uani 0.426(7) 1 d DG . P A 2
H24B H 1.0099 0.6309 0.4607 0.089 Uiso 0.426(7) 1 calc R U P A 2
C25A C 0.931(2) 0.7005(16) 0.3833(5) 0.0604(14) Uani 0.426(7) 1 d DG . P A 2
C26A C 0.755(2) 1.027(2) 0.3719(8) 0.101(3) Uani 0.426(7) 1 d D . P A 2
H26D H 0.7412 1.0241 0.3287 0.152 Uiso 0.426(7) 1 calc R U P A 2
H26E H 0.7911 1.1135 0.3836 0.152 Uiso 0.426(7) 1 calc R U P A 2
H26F H 0.6801 1.0184 0.3901 0.152 Uiso 0.426(7) 1 calc R U P A 2
C27A C 0.959(3) 0.584(2) 0.3436(9) 0.105(4) Uani 0.426(7) 1 d D . P A 2
H27D H 0.9654 0.5015 0.3670 0.157 Uiso 0.426(7) 1 calc R U P A 2
H27E H 1.0333 0.6015 0.3259 0.157 Uiso 0.426(7) 1 calc R U P A 2
H27F H 0.8963 0.5745 0.3122 0.157 Uiso 0.426(7) 1 calc R U 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
S1 C4 1.722(7) . ?
S1 C1 1.740(3) . ?
S1 C4A 1.829(10) . ?
S2 C2 1.752(3) . ?
S2 C12 1.755(7) . ?
S2 C12A 1.757(10) . ?
S3 C20A 1.718(8) . ?
S3 C3 1.750(3) . ?
S3 C20 1.781(5) . ?
N1 C2 1.327(3) . ?
N1 C1 1.334(3) . ?
N2 C3 1.333(3) . ?
N2 C2 1.333(3) . ?
N3 C1 1.324(3) . ?
N3 C3 1.326(3) . ?
C4 C5 1.3900 . ?
C4 C9 1.3900 . ?
C5 C6 1.3900 . ?
C5 C10 1.505(8) . ?
C6 C7 1.3900 . ?
C6 H6A 0.9500 . ?
C7 C8 1.3900 . ?
C7 H7A 0.9500 . ?
C8 C9 1.3900 . ?
C8 H8A 0.9500 . ?
C9 C11 1.513(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C4A C5A 1.3900 . ?
C4A C9A 1.3900 . ?
C5A C6A 1.3900 . ?
C5A C10A 1.509(11) . ?
C6A C7A 1.3900 . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.3900 . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.3900 . ?
C8A H8AA 0.9500 . ?
C9A C11A 1.502(11) . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12 C13 1.3900 . ?
C12 C17 1.3900 . ?
C13 C14 1.3900 . ?
C13 C18 1.532(8) . ?
C14 C15 1.3900 . ?
C14 H14A 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15A 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16A 0.9500 . ?
C17 C19 1.514(9) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C12A C13A 1.3900 . ?
C12A C17A 1.3900 . ?
C13A C14A 1.3900 . ?
C13A C18A 1.525(11) . ?
C14A C15A 1.3900 . ?
C14A H14B 0.9500 . ?
C15A C16A 1.3900 . ?
C15A H15B 0.9500 . ?
C16A C17A 1.3900 . ?
C16A H16B 0.9500 . ?
C17A C19A 1.509(11) . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C21 C22 1.3900 . ?
C21 C26 1.512(8) . ?
C22 C23 1.3900 . ?
C22 H22A 0.9500 . ?
C23 C24 1.3900 . ?
C23 H23A 0.9500 . ?
C24 C25 1.3900 . ?
C24 H24A 0.9500 . ?
C25 C27 1.514(8) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C20A C21A 1.3900 . ?
C20A C25A 1.3900 . ?
C21A C22A 1.3900 . ?
C21A C26A 1.509(11) . ?
C22A C23A 1.3900 . ?
C22A H22B 0.9500 . ?
C23A C24A 1.3900 . ?
C23A H23B 0.9500 . ?
C24A C25A 1.3900 . ?
C24A H24B 0.9500 . ?
C25A C27A 1.513(11) . ?
C26A H26D 0.9800 . ?
C26A H26E 0.9800 . ?
C26A H26F 0.9800 . ?
C27A H27D 0.9800 . ?
C27A H27E 0.9800 . ?
C27A H27F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C1 106.8(4) . . ?
C1 S1 C4A 97.2(6) . . ?
C2 S2 C12 101.5(6) . . ?
C2 S2 C12A 106.7(9) . . ?
C20A S3 C3 104.7(10) . . ?
C3 S3 C20 100.5(7) . . ?
C2 N1 C1 113.3(2) . . ?
C3 N2 C2 112.9(2) . . ?
C1 N3 C3 113.4(2) . . ?
N3 C1 N1 126.6(2) . . ?
N3 C1 S1 119.69(18) . . ?
N1 C1 S1 113.68(19) . . ?
N1 C2 N2 126.8(2) . . ?
N1 C2 S2 119.8(2) . . ?
N2 C2 S2 113.4(2) . . ?
N3 C3 N2 126.9(2) . . ?
N3 C3 S3 118.9(2) . . ?
N2 C3 S3 114.2(2) . . ?
C5 C4 C9 120.0 . . ?
C5 C4 S1 118.2(6) . . ?
C9 C4 S1 121.7(6) . . ?
C4 C5 C6 120.0 . . ?
C4 C5 C10 123.8(7) . . ?
C6 C5 C10 116.1(7) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C8 C9 C4 120.0 . . ?
C8 C9 C11 119.9(9) . . ?
C4 C9 C11 120.1(9) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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 . . ?
C5A C4A C9A 120.0 . . ?
C5A C4A S1 122.0(8) . . ?
C9A C4A S1 116.0(8) . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A C10A 120.7(10) . . ?
C4A C5A C10A 119.3(10) . . ?
C5A C6A C7A 120.0 . . ?
C5A C6A H6AA 120.0 . . ?
C7A C6A H6AA 120.0 . . ?
C6A C7A C8A 120.0 . . ?
C6A C7A H7AA 120.0 . . ?
C8A C7A H7AA 120.0 . . ?
C9A C8A C7A 120.0 . . ?
C9A C8A H8AA 120.0 . . ?
C7A C8A H8AA 120.0 . . ?
C8A C9A C4A 120.0 . . ?
C8A C9A C11A 115.8(12) . . ?
C4A C9A C11A 124.2(12) . . ?
C5A C10A H10D 109.5 . . ?
C5A C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
C5A C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C9A C11A H11D 109.5 . . ?
C9A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C9A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C13 C12 C17 120.0 . . ?
C13 C12 S2 113.7(6) . . ?
C17 C12 S2 125.4(6) . . ?
C12 C13 C14 120.0 . . ?
C12 C13 C18 123.9(6) . . ?
C14 C13 C18 115.6(7) . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C16 C17 C12 120.0 . . ?
C16 C17 C19 119.6(7) . . ?
C12 C17 C19 120.3(7) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13A C12A C17A 120.0 . . ?
C13A C12A S2 127.1(8) . . ?
C17A C12A S2 112.8(8) . . ?
C12A C13A C14A 120.0 . . ?
C12A C13A C18A 119.2(9) . . ?
C14A C13A C18A 120.3(9) . . ?
C15A C14A C13A 120.0 . . ?
C15A C14A H14B 120.0 . . ?
C13A C14A H14B 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A H15B 120.0 . . ?
C14A C15A H15B 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C15A C16A H16B 120.0 . . ?
C17A C16A H16B 120.0 . . ?
C16A C17A C12A 120.0 . . ?
C16A C17A C19A 115.2(10) . . ?
C12A C17A C19A 123.9(10) . . ?
C13A C18A H18D 109.5 . . ?
C13A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C13A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C17A C19A H19D 109.5 . . ?
C17A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C17A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C21 C20 C25 120.0 . . ?
C21 C20 S3 128.5(5) . . ?
C25 C20 S3 110.8(5) . . ?
C20 C21 C22 120.0 . . ?
C20 C21 C26 119.8(5) . . ?
C22 C21 C26 120.2(5) . . ?
C23 C22 C21 120.0 . . ?
C23 C22 H22A 120.0 . . ?
C21 C22 H22A 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24A 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C24 C25 C20 120.0 . . ?
C24 C25 C27 115.5(7) . . ?
C20 C25 C27 124.4(6) . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C21A C20A C25A 120.0 . . ?
C21A C20A S3 108.1(7) . . ?
C25A C20A S3 131.9(7) . . ?
C20A C21A C22A 120.0 . . ?
C20A C21A C26A 125.3(8) . . ?
C22A C21A C26A 114.4(8) . . ?
C23A C22A C21A 120.0 . . ?
C23A C22A H22B 120.0 . . ?
C21A C22A H22B 120.0 . . ?
C22A C23A C24A 120.0 . . ?
C22A C23A H23B 120.0 . . ?
C24A C23A H23B 120.0 . . ?
C23A C24A C25A 120.0 . . ?
C23A C24A H24B 120.0 . . ?
C25A C24A H24B 120.0 . . ?
C24A C25A C20A 120.0 . . ?
C24A C25A C27A 122.5(10) . . ?
C20A C25A C27A 117.5(9) . . ?
C21A C26A H26D 109.5 . . ?
C21A C26A H26E 109.5 . . ?
H26D C26A H26E 109.5 . . ?
C21A C26A H26F 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?
C25A C27A H27D 109.5 . . ?
C25A C27A H27E 109.5 . . ?
H27D C27A H27E 109.5 . . ?
C25A C27A H27F 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 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
C3 N3 C1 N1 -1.2(4) . . . . ?
C3 N3 C1 S1 179.5(2) . . . . ?
C2 N1 C1 N3 1.3(4) . . . . ?
C2 N1 C1 S1 -179.3(2) . . . . ?
C4 S1 C1 N3 -9.1(5) . . . . ?
C4A S1 C1 N3 -10.8(5) . . . . ?
C4 S1 C1 N1 171.4(4) . . . . ?
C4A S1 C1 N1 169.7(5) . . . . ?
C1 N1 C2 N2 -0.1(4) . . . . ?
C1 N1 C2 S2 178.8(2) . . . . ?
C3 N2 C2 N1 -0.9(4) . . . . ?
C3 N2 C2 S2 -179.9(2) . . . . ?
C12 S2 C2 N1 11.5(4) . . . . ?
C12A S2 C2 N1 14.2(6) . . . . ?
C12 S2 C2 N2 -169.5(4) . . . . ?
C12A S2 C2 N2 -166.7(6) . . . . ?
C1 N3 C3 N2 -0.1(4) . . . . ?
C1 N3 C3 S3 179.1(2) . . . . ?
C2 N2 C3 N3 1.1(5) . . . . ?
C2 N2 C3 S3 -178.2(2) . . . . ?
C20A S3 C3 N3 8.1(5) . . . . ?
C20 S3 C3 N3 3.4(4) . . . . ?
C20A S3 C3 N2 -172.6(5) . . . . ?
C20 S3 C3 N2 -177.2(4) . . . . ?
C1 S1 C4 C5 103.0(7) . . . . ?
C1 S1 C4 C9 -72.9(6) . . . . ?
C9 C4 C5 C6 0.0 . . . . ?
S1 C4 C5 C6 -176.0(9) . . . . ?
C9 C4 C5 C10 178.3(11) . . . . ?
S1 C4 C5 C10 2.3(12) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C10 C5 C6 C7 -178.4(10) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C7 C8 C9 C4 0.0 . . . . ?
C7 C8 C9 C11 179(2) . . . . ?
C5 C4 C9 C8 0.0 . . . . ?
S1 C4 C9 C8 175.9(9) . . . . ?
C5 C4 C9 C11 -179(2) . . . . ?
S1 C4 C9 C11 -3(2) . . . . ?
C1 S1 C4A C5A 110.5(10) . . . . ?
C1 S1 C4A C9A -85.7(7) . . . . ?
C9A C4A C5A C6A 0.0 . . . . ?
S1 C4A C5A C6A 163.2(13) . . . . ?
C9A C4A C5A C10A -178.9(15) . . . . ?
S1 C4A C5A C10A -15.7(16) . . . . ?
C4A C5A C6A C7A 0.0 . . . . ?
C10A C5A C6A C7A 178.8(15) . . . . ?
C5A C6A C7A C8A 0.0 . . . . ?
C6A C7A C8A C9A 0.0 . . . . ?
C7A C8A C9A C4A 0.0 . . . . ?
C7A C8A C9A C11A 179(3) . . . . ?
C5A C4A C9A C8A 0.0 . . . . ?
S1 C4A C9A C8A -164.2(12) . . . . ?
C5A C4A C9A C11A -179(3) . . . . ?
S1 C4A C9A C11A 17(3) . . . . ?
C2 S2 C12 C13 77.2(7) . . . . ?
C2 S2 C12 C17 -113.5(9) . . . . ?
C17 C12 C13 C14 0.0 . . . . ?
S2 C12 C13 C14 169.9(12) . . . . ?
C17 C12 C13 C18 -171.6(15) . . . . ?
S2 C12 C13 C18 -1.6(13) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C18 C13 C14 C15 172.2(14) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C12 0.0 . . . . ?
C15 C16 C17 C19 -177.2(18) . . . . ?
C13 C12 C17 C16 0.0 . . . . ?
S2 C12 C17 C16 -168.7(13) . . . . ?
C13 C12 C17 C19 177.2(18) . . . . ?
S2 C12 C17 C19 8.5(16) . . . . ?
C2 S2 C12A C13A 69.9(14) . . . . ?
C2 S2 C12A C17A -106.8(9) . . . . ?
C17A C12A C13A C14A 0.0 . . . . ?
S2 C12A C13A C14A -176(2) . . . . ?
C17A C12A C13A C18A 172(2) . . . . ?
S2 C12A C13A C18A -4.2(19) . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
C18A C13A C14A C15A -172(2) . . . . ?
C13A C14A C15A C16A 0.0 . . . . ?
C14A C15A C16A C17A 0.0 . . . . ?
C15A C16A C17A C12A 0.0 . . . . ?
C15A C16A C17A C19A 169(2) . . . . ?
C13A C12A C17A C16A 0.0 . . . . ?
S2 C12A C17A C16A 176.9(17) . . . . ?
C13A C12A C17A C19A -168(3) . . . . ?
S2 C12A C17A C19A 8(2) . . . . ?
C3 S3 C20 C21 -95.0(10) . . . . ?
C3 S3 C20 C25 94.4(6) . . . . ?
C25 C20 C21 C22 0.0 . . . . ?
S3 C20 C21 C22 -169.9(14) . . . . ?
C25 C20 C21 C26 -179.0(14) . . . . ?
S3 C20 C21 C26 11.2(14) . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C26 C21 C22 C23 179.0(14) . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C20 0.0 . . . . ?
C23 C24 C25 C27 -177.1(17) . . . . ?
C21 C20 C25 C24 0.0 . . . . ?
S3 C20 C25 C24 171.5(12) . . . . ?
C21 C20 C25 C27 176.8(18) . . . . ?
S3 C20 C25 C27 -11.7(15) . . . . ?
C3 S3 C20A C21A -90.6(10) . . . . ?
C3 S3 C20A C25A 90.2(13) . . . . ?
C25A C20A C21A C22A 0.0 . . . . ?
S3 C20A C21A C22A -179.3(17) . . . . ?
C25A C20A C21A C26A -173(2) . . . . ?
S3 C20A C21A C26A 7.3(19) . . . . ?
C20A C21A C22A C23A 0.0 . . . . ?
C26A C21A C22A C23A 174.0(19) . . . . ?
C21A C22A C23A C24A 0.0 . . . . ?
C22A C23A C24A C25A 0.0 . . . . ?
C23A C24A C25A C20A 0.0 . . . . ?
C23A C24A C25A C27A -178(3) . . . . ?
C21A C20A C25A C24A 0.0 . . . . ?
S3 C20A C25A C24A 179(2) . . . . ?
C21A C20A C25A C27A 178(2) . . . . ?
S3 C20A C25A C27A -2(2) . . . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.284
_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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1436793'
_audit_update_record             
;
2015-11-13 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT412_shelx               
;
PROBLEM: Short Intra XH3 .. XHn     H34B   ..  H35B    ..       1.69 Ang.  
RESPONSE: The H's are attached to adjacent CH3 substituents on a 
penta-methyl phenyl ring thus there are closer than normal contacts
due to steric crowding.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H45 N3 S3'
_chemical_formula_sum            'C36 H45 N3 S3'
_chemical_formula_weight         615.93

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_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                   13.491(5)
_cell_length_b                   10.406(4)
_cell_length_c                   23.955(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.092(7)
_cell_angle_gamma                90
_cell_volume                     3354(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1143
_cell_measurement_theta_min      2.474
_cell_measurement_theta_max      26.353
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.273
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17498
_diffrn_reflns_av_unetI/netI     0.2422
_diffrn_reflns_av_R_equivalents  0.2114
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.683
_diffrn_reflns_theta_max         25.252
_diffrn_reflns_theta_full        25.252
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6079
_reflns_number_gt                1959
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex 2'
_computing_cell_refinement       'Bruker Saint'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6079
_refine_ls_number_parameters     394
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.2417
_refine_ls_R_factor_gt           0.0807
_refine_ls_wR_factor_ref         0.1836
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.934
_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_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 0.48754(13) 0.26787(18) 0.84257(7) 0.0877(7) Uani 1 1 d . U . . .
S2 S 0.78598(14) 0.17526(19) 0.72620(7) 0.0983(7) Uani 1 1 d . U . . .
S3 S 0.47265(12) 0.41889(16) 0.63153(7) 0.0731(6) Uani 1 1 d . U . . .
N1 N 0.6290(4) 0.2341(5) 0.77736(19) 0.0719(16) Uani 1 1 d . . . . .
N2 N 0.6265(3) 0.2975(4) 0.6822(2) 0.0598(14) Uani 1 1 d . . . . .
N3 N 0.4872(3) 0.3395(4) 0.73495(19) 0.0595(14) Uani 1 1 d . . . . .
C1 C 0.5370(5) 0.2847(6) 0.7774(2) 0.0623(18) Uani 1 1 d . . . . .
C2 C 0.6680(4) 0.2435(5) 0.7274(3) 0.0603(17) Uani 1 1 d . . . . .
C3 C 0.5361(4) 0.3432(5) 0.6878(2) 0.0516(15) Uani 1 1 d . . . . .
C4 C 0.3659(4) 0.3322(6) 0.8323(2) 0.0532(16) Uani 1 1 d . . . . .
C5 C 0.2872(6) 0.2535(6) 0.8127(2) 0.0613(17) Uani 1 1 d . . . . .
C6 C 0.1910(5) 0.3034(7) 0.8083(2) 0.0622(17) Uani 1 1 d . . . . .
C7 C 0.1743(5) 0.4292(7) 0.8271(2) 0.0587(17) Uani 1 1 d . . . . .
C8 C 0.2538(5) 0.5072(6) 0.8455(2) 0.0624(18) Uani 1 1 d . . . . .
C9 C 0.3498(5) 0.4603(6) 0.8477(2) 0.0568(16) Uani 1 1 d . . . . .
C10 C 0.3052(5) 0.1153(5) 0.7965(3) 0.101(3) Uani 1 1 d . . . . .
H10A H 0.3730 0.0926 0.8070 0.152 Uiso 1 1 calc R U . . .
H10B H 0.2924 0.1055 0.7568 0.152 Uiso 1 1 calc R U . . .
H10C H 0.2617 0.0600 0.8155 0.152 Uiso 1 1 calc R U . . .
C11 C 0.1065(5) 0.2210(6) 0.7838(3) 0.098(2) Uani 1 1 d . . . . .
H11A H 0.0586 0.2094 0.8112 0.147 Uiso 1 1 calc R U . . .
H11B H 0.1318 0.1389 0.7735 0.147 Uiso 1 1 calc R U . . .
H11C H 0.0755 0.2625 0.7514 0.147 Uiso 1 1 calc R U . . .
C12 C 0.0678(5) 0.4784(6) 0.8253(3) 0.095(2) Uani 1 1 d . . . . .
H12A H 0.0603 0.5347 0.8565 0.142 Uiso 1 1 calc R U . . .
H12B H 0.0230 0.4071 0.8272 0.142 Uiso 1 1 calc R U . . .
H12C H 0.0528 0.5246 0.7910 0.142 Uiso 1 1 calc R U . . .
C13 C 0.2341(5) 0.6435(6) 0.8636(3) 0.111(3) Uani 1 1 d . . . . .
H13A H 0.2247 0.6449 0.9029 0.167 Uiso 1 1 calc R U . . .
H13B H 0.1754 0.6753 0.8432 0.167 Uiso 1 1 calc R U . . .
H13C H 0.2897 0.6968 0.8562 0.167 Uiso 1 1 calc R U . . .
C14 C 0.4348(5) 0.5461(6) 0.8664(3) 0.102(2) Uani 1 1 d . . . . .
H14A H 0.4139 0.6054 0.8939 0.154 Uiso 1 1 calc R U . . .
H14B H 0.4562 0.5929 0.8349 0.154 Uiso 1 1 calc R U . . .
H14C H 0.4888 0.4950 0.8825 0.154 Uiso 1 1 calc R U . . .
C15 C 0.8148(4) 0.1939(7) 0.6551(2) 0.0601(18) Uani 1 1 d . . . . .
C16 C 0.8736(4) 0.2985(6) 0.6420(3) 0.0640(18) Uani 1 1 d . . . . .
C17 C 0.9101(5) 0.3023(6) 0.5891(3) 0.0653(19) Uani 1 1 d . . . . .
C18 C 0.8877(5) 0.2073(7) 0.5512(3) 0.069(2) Uani 1 1 d . . . . .
C19 C 0.8232(5) 0.1083(7) 0.5635(3) 0.0714(19) Uani 1 1 d . . . . .
C20 C 0.7879(4) 0.1004(7) 0.6168(3) 0.0703(19) Uani 1 1 d . . . . .
C21 C 0.8957(6) 0.4070(7) 0.6827(3) 0.120(3) Uani 1 1 d . . . . .
H21A H 0.8635 0.3909 0.7165 0.180 Uiso 1 1 calc R U . . .
H21B H 0.8714 0.4862 0.6663 0.180 Uiso 1 1 calc R U . . .
H21C H 0.9661 0.4131 0.6912 0.180 Uiso 1 1 calc R U . . .
C22 C 0.9814(5) 0.4095(6) 0.5754(3) 0.121(3) Uani 1 1 d . . . . .
H22A H 1.0020 0.3974 0.5382 0.182 Uiso 1 1 calc R U . . .
H22B H 1.0386 0.4076 0.6016 0.182 Uiso 1 1 calc R U . . .
H22C H 0.9486 0.4910 0.5776 0.182 Uiso 1 1 calc R U . . .
C23 C 0.9338(5) 0.2048(7) 0.4943(3) 0.114(3) Uani 1 1 d . . . . .
H23A H 0.9504 0.1180 0.4852 0.171 Uiso 1 1 calc R U . . .
H23B H 0.9928 0.2566 0.4963 0.171 Uiso 1 1 calc R U . . .
H23C H 0.8869 0.2383 0.4660 0.171 Uiso 1 1 calc R U . . .
C24 C 0.7962(6) 0.0044(7) 0.5206(3) 0.133(3) Uani 1 1 d . . . . .
H24A H 0.7938 0.0409 0.4837 0.200 Uiso 1 1 calc R U . . .
H24B H 0.7324 -0.0308 0.5273 0.200 Uiso 1 1 calc R U . . .
H24C H 0.8454 -0.0624 0.5236 0.200 Uiso 1 1 calc R U . . .
C25 C 0.7213(5) -0.0102(7) 0.6322(3) 0.132(3) Uani 1 1 d . . . . .
H25A H 0.7005 0.0028 0.6693 0.197 Uiso 1 1 calc R U . . .
H25B H 0.7573 -0.0896 0.6309 0.197 Uiso 1 1 calc R U . . .
H25C H 0.6639 -0.0136 0.6061 0.197 Uiso 1 1 calc R U . . .
C26 C 0.5607(4) 0.4225(6) 0.5792(2) 0.0550(16) Uani 1 1 d . . . . .
C27 C 0.6290(5) 0.5222(6) 0.5803(3) 0.0670(18) Uani 1 1 d . . . . .
C28 C 0.6913(5) 0.5330(7) 0.5362(3) 0.0731(19) Uani 1 1 d . . . . .
C29 C 0.6850(5) 0.4462(7) 0.4937(3) 0.071(2) Uani 1 1 d . . . . .
C30 C 0.6195(5) 0.3441(6) 0.4940(2) 0.0694(19) Uani 1 1 d . . . . .
C31 C 0.5563(5) 0.3325(6) 0.5373(2) 0.0659(18) Uani 1 1 d . . . . .
C32 C 0.6384(5) 0.6197(7) 0.6274(3) 0.116(3) Uani 1 1 d . . . . .
H32A H 0.7057 0.6211 0.6434 0.174 Uiso 1 1 calc R U . . .
H32B H 0.5947 0.5964 0.6557 0.174 Uiso 1 1 calc R U . . .
H32C H 0.6207 0.7033 0.6130 0.174 Uiso 1 1 calc R U . . .
C33 C 0.7660(5) 0.6418(7) 0.5357(3) 0.132(3) Uani 1 1 d . . . . .
H33A H 0.8263 0.6110 0.5214 0.199 Uiso 1 1 calc R U . . .
H33B H 0.7799 0.6732 0.5731 0.199 Uiso 1 1 calc R U . . .
H33C H 0.7391 0.7101 0.5123 0.199 Uiso 1 1 calc R U . . .
C34 C 0.7522(5) 0.4590(7) 0.4446(3) 0.119(3) Uani 1 1 d . . . . .
H34A H 0.7450 0.5434 0.4287 0.178 Uiso 1 1 calc R U . . .
H34B H 0.7334 0.3959 0.4166 0.178 Uiso 1 1 calc R U . . .
H34C H 0.8203 0.4456 0.4580 0.178 Uiso 1 1 calc R U . . .
C35 C 0.6131(6) 0.2460(7) 0.4468(3) 0.126(3) Uani 1 1 d . . . . .
H35A H 0.6195 0.1611 0.4623 0.188 Uiso 1 1 calc R U . . .
H35B H 0.6656 0.2611 0.4226 0.188 Uiso 1 1 calc R U . . .
H35C H 0.5501 0.2540 0.4258 0.188 Uiso 1 1 calc R U . . .
C36 C 0.4842(6) 0.2202(6) 0.5390(3) 0.117(3) Uani 1 1 d . . . . .
H36A H 0.4476 0.2269 0.5718 0.176 Uiso 1 1 calc R U . . .
H36B H 0.5207 0.1409 0.5401 0.176 Uiso 1 1 calc R U . . .
H36C H 0.4390 0.2219 0.5062 0.176 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.749(5) . ?
S1 C4 1.774(6) . ?
S2 C2 1.745(6) . ?
S2 C15 1.784(5) . ?
S3 C3 1.734(5) . ?
S3 C26 1.788(5) . ?
N1 C2 1.345(6) . ?
N1 C1 1.348(6) . ?
N2 C2 1.310(6) . ?
N2 C3 1.326(6) . ?
N3 C1 1.309(7) . ?
N3 C3 1.348(6) . ?
C4 C5 1.394(7) . ?
C4 C9 1.404(7) . ?
C5 C6 1.395(8) . ?
C5 C10 1.514(7) . ?
C6 C7 1.408(7) . ?
C6 C11 1.511(8) . ?
C7 C8 1.392(8) . ?
C7 C12 1.523(7) . ?
C8 C9 1.382(7) . ?
C8 C13 1.511(7) . ?
C9 C14 1.497(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.368(8) . ?
C15 C16 1.396(7) . ?
C16 C17 1.393(7) . ?
C16 C21 1.506(8) . ?
C17 C18 1.363(8) . ?
C17 C22 1.524(8) . ?
C18 C19 1.393(8) . ?
C18 C23 1.537(7) . ?
C19 C20 1.397(8) . ?
C19 C24 1.518(8) . ?
C20 C25 1.522(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C31 1.372(7) . ?
C26 C27 1.387(7) . ?
C27 C28 1.403(7) . ?
C27 C32 1.515(8) . ?
C28 C29 1.358(8) . ?
C28 C33 1.516(8) . ?
C29 C30 1.383(8) . ?
C29 C34 1.541(7) . ?
C30 C31 1.393(7) . ?
C30 C35 1.520(8) . ?
C31 C36 1.523(8) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 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 C4 104.3(3) . . ?
C2 S2 C15 103.4(3) . . ?
C3 S3 C26 103.9(3) . . ?
C2 N1 C1 113.0(5) . . ?
C2 N2 C3 114.3(4) . . ?
C1 N3 C3 114.1(5) . . ?
N3 C1 N1 126.2(5) . . ?
N3 C1 S1 122.0(5) . . ?
N1 C1 S1 111.8(5) . . ?
N2 C2 N1 126.6(5) . . ?
N2 C2 S2 119.8(4) . . ?
N1 C2 S2 113.6(5) . . ?
N2 C3 N3 125.7(5) . . ?
N2 C3 S3 119.4(4) . . ?
N3 C3 S3 114.9(4) . . ?
C5 C4 C9 121.2(6) . . ?
C5 C4 S1 120.0(5) . . ?
C9 C4 S1 118.7(5) . . ?
C4 C5 C6 119.3(6) . . ?
C4 C5 C10 120.8(6) . . ?
C6 C5 C10 120.0(7) . . ?
C5 C6 C7 119.4(6) . . ?
C5 C6 C11 119.4(6) . . ?
C7 C6 C11 121.2(7) . . ?
C8 C7 C6 120.4(6) . . ?
C8 C7 C12 121.1(6) . . ?
C6 C7 C12 118.5(7) . . ?
C9 C8 C7 120.3(6) . . ?
C9 C8 C13 120.3(6) . . ?
C7 C8 C13 119.4(6) . . ?
C8 C9 C4 119.2(6) . . ?
C8 C9 C14 119.7(6) . . ?
C4 C9 C14 121.1(6) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 122.2(5) . . ?
C20 C15 S2 119.8(5) . . ?
C16 C15 S2 117.7(6) . . ?
C17 C16 C15 118.0(6) . . ?
C17 C16 C21 120.0(6) . . ?
C15 C16 C21 121.9(6) . . ?
C18 C17 C16 120.7(6) . . ?
C18 C17 C22 120.0(6) . . ?
C16 C17 C22 119.2(7) . . ?
C17 C18 C19 120.5(6) . . ?
C17 C18 C23 121.2(6) . . ?
C19 C18 C23 118.3(7) . . ?
C18 C19 C20 119.8(7) . . ?
C18 C19 C24 120.4(6) . . ?
C20 C19 C24 119.8(7) . . ?
C15 C20 C19 118.6(6) . . ?
C15 C20 C25 120.6(6) . . ?
C19 C20 C25 120.7(7) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C31 C26 C27 121.3(5) . . ?
C31 C26 S3 120.2(5) . . ?
C27 C26 S3 118.4(5) . . ?
C26 C27 C28 118.6(6) . . ?
C26 C27 C32 122.4(6) . . ?
C28 C27 C32 119.0(6) . . ?
C29 C28 C27 120.2(6) . . ?
C29 C28 C33 119.8(6) . . ?
C27 C28 C33 120.0(7) . . ?
C28 C29 C30 120.9(6) . . ?
C28 C29 C34 120.3(7) . . ?
C30 C29 C34 118.8(7) . . ?
C29 C30 C31 119.7(6) . . ?
C29 C30 C35 121.0(6) . . ?
C31 C30 C35 119.3(7) . . ?
C26 C31 C30 119.3(6) . . ?
C26 C31 C36 119.9(5) . . ?
C30 C31 C36 120.8(6) . . ?
C27 C32 H32A 109.5 . . ?
C27 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C27 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C28 C33 H33A 109.5 . . ?
C28 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C28 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C29 C34 H34A 109.5 . . ?
C29 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C29 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C30 C35 H35A 109.5 . . ?
C30 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C30 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
C3 N3 C1 N1 -0.1(9) . . . . ?
C3 N3 C1 S1 -179.3(4) . . . . ?
C2 N1 C1 N3 -0.5(9) . . . . ?
C2 N1 C1 S1 178.8(4) . . . . ?
C4 S1 C1 N3 2.3(6) . . . . ?
C4 S1 C1 N1 -177.0(5) . . . . ?
C3 N2 C2 N1 -1.9(9) . . . . ?
C3 N2 C2 S2 178.5(4) . . . . ?
C1 N1 C2 N2 1.6(9) . . . . ?
C1 N1 C2 S2 -178.7(4) . . . . ?
C15 S2 C2 N2 -3.4(6) . . . . ?
C15 S2 C2 N1 176.9(5) . . . . ?
C2 N2 C3 N3 1.1(9) . . . . ?
C2 N2 C3 S3 179.3(4) . . . . ?
C1 N3 C3 N2 -0.1(9) . . . . ?
C1 N3 C3 S3 -178.5(4) . . . . ?
C26 S3 C3 N2 -4.2(5) . . . . ?
C26 S3 C3 N3 174.2(4) . . . . ?
C1 S1 C4 C5 87.6(5) . . . . ?
C1 S1 C4 C9 -96.5(4) . . . . ?
C9 C4 C5 C6 0.1(8) . . . . ?
S1 C4 C5 C6 175.8(4) . . . . ?
C9 C4 C5 C10 -179.6(5) . . . . ?
S1 C4 C5 C10 -3.9(7) . . . . ?
C4 C5 C6 C7 -4.2(8) . . . . ?
C10 C5 C6 C7 175.6(5) . . . . ?
C4 C5 C6 C11 176.3(5) . . . . ?
C10 C5 C6 C11 -3.9(8) . . . . ?
C5 C6 C7 C8 5.5(8) . . . . ?
C11 C6 C7 C8 -175.0(5) . . . . ?
C5 C6 C7 C12 -176.2(5) . . . . ?
C11 C6 C7 C12 3.3(8) . . . . ?
C6 C7 C8 C9 -2.6(8) . . . . ?
C12 C7 C8 C9 179.1(5) . . . . ?
C6 C7 C8 C13 177.8(5) . . . . ?
C12 C7 C8 C13 -0.5(8) . . . . ?
C7 C8 C9 C4 -1.5(8) . . . . ?
C13 C8 C9 C4 178.1(5) . . . . ?
C7 C8 C9 C14 178.7(5) . . . . ?
C13 C8 C9 C14 -1.7(8) . . . . ?
C5 C4 C9 C8 2.7(8) . . . . ?
S1 C4 C9 C8 -173.0(4) . . . . ?
C5 C4 C9 C14 -177.5(5) . . . . ?
S1 C4 C9 C14 6.8(7) . . . . ?
C2 S2 C15 C20 -89.1(5) . . . . ?
C2 S2 C15 C16 97.5(5) . . . . ?
C20 C15 C16 C17 -3.8(9) . . . . ?
S2 C15 C16 C17 169.5(5) . . . . ?
C20 C15 C16 C21 174.6(6) . . . . ?
S2 C15 C16 C21 -12.1(8) . . . . ?
C15 C16 C17 C18 0.9(9) . . . . ?
C21 C16 C17 C18 -177.5(6) . . . . ?
C15 C16 C17 C22 -175.0(5) . . . . ?
C21 C16 C17 C22 6.6(9) . . . . ?
C16 C17 C18 C19 3.6(10) . . . . ?
C22 C17 C18 C19 179.5(6) . . . . ?
C16 C17 C18 C23 -175.3(6) . . . . ?
C22 C17 C18 C23 0.5(10) . . . . ?
C17 C18 C19 C20 -5.4(10) . . . . ?
C23 C18 C19 C20 173.6(6) . . . . ?
C17 C18 C19 C24 178.4(6) . . . . ?
C23 C18 C19 C24 -2.6(9) . . . . ?
C16 C15 C20 C19 2.0(10) . . . . ?
S2 C15 C20 C19 -171.2(5) . . . . ?
C16 C15 C20 C25 -178.2(6) . . . . ?
S2 C15 C20 C25 8.6(8) . . . . ?
C18 C19 C20 C15 2.6(9) . . . . ?
C24 C19 C20 C15 178.8(6) . . . . ?
C18 C19 C20 C25 -177.2(6) . . . . ?
C24 C19 C20 C25 -0.9(10) . . . . ?
C3 S3 C26 C31 99.0(5) . . . . ?
C3 S3 C26 C27 -84.7(5) . . . . ?
C31 C26 C27 C28 2.8(9) . . . . ?
S3 C26 C27 C28 -173.5(5) . . . . ?
C31 C26 C27 C32 -177.3(6) . . . . ?
S3 C26 C27 C32 6.4(8) . . . . ?
C26 C27 C28 C29 -0.7(10) . . . . ?
C32 C27 C28 C29 179.4(6) . . . . ?
C26 C27 C28 C33 179.2(6) . . . . ?
C32 C27 C28 C33 -0.6(10) . . . . ?
C27 C28 C29 C30 -1.8(10) . . . . ?
C33 C28 C29 C30 178.2(6) . . . . ?
C27 C28 C29 C34 179.0(6) . . . . ?
C33 C28 C29 C34 -1.0(10) . . . . ?
C28 C29 C30 C31 2.4(10) . . . . ?
C34 C29 C30 C31 -178.5(6) . . . . ?
C28 C29 C30 C35 -179.3(7) . . . . ?
C34 C29 C30 C35 -0.1(9) . . . . ?
C27 C26 C31 C30 -2.3(9) . . . . ?
S3 C26 C31 C30 173.9(5) . . . . ?
C27 C26 C31 C36 176.7(6) . . . . ?
S3 C26 C31 C36 -7.1(8) . . . . ?
C29 C30 C31 C26 -0.3(9) . . . . ?
C35 C30 C31 C26 -178.6(6) . . . . ?
C29 C30 C31 C36 -179.3(6) . . . . ?
C35 C30 C31 C36 2.4(9) . . . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1452878'
_audit_update_record             
;
2016-02-11 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H3 F12 N3 S3'
_chemical_formula_sum            'C21 H3 F12 N3 S3'
_chemical_formula_weight         621.44

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'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

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'

_cell_length_a                   9.899(3)
_cell_length_b                   12.113(3)
_cell_length_c                   20.030(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2401.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2516
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      20.55

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.419
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5868
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4627
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.845
_diffrn_reflns_theta_max         28.240
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_point_group_measured_fraction_full 0.816
_reflns_number_total             4627
_reflns_number_gt                2203
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.524
_reflns_Friedel_fraction_max     0.551
_reflns_Friedel_fraction_full    0.623

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.3150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 681 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4627
_refine_ls_number_parameters     352
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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_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 0.6992(2) 0.77772(13) 0.71570(8) 0.0819(6) Uani 1 1 d . . . . .
S2 S 0.7007(2) 0.42167(15) 0.57298(9) 0.0921(7) Uani 1 1 d . . . . .
S3 S 0.4272(2) 0.77845(14) 0.49229(10) 0.0980(7) Uani 1 1 d . . . . .
F1 F 0.4402(4) 0.8949(3) 0.7512(2) 0.0943(12) Uani 1 1 d . . . . .
F2 F 0.3743(4) 1.1036(3) 0.7243(2) 0.1053(15) Uani 1 1 d . . . . .
F3 F 0.7950(5) 1.1573(4) 0.6205(3) 0.158(2) Uani 1 1 d . . . . .
F4 F 0.8618(5) 0.9478(4) 0.6465(3) 0.1265(17) Uani 1 1 d . . . . .
F5 F 0.5076(5) 0.2458(3) 0.5343(2) 0.1212(16) Uani 1 1 d . . . . .
F6 F 0.4336(4) 0.1847(4) 0.4120(3) 0.1359(18) Uani 1 1 d . . . . .
F7 F 0.6931(6) 0.4674(4) 0.3207(2) 0.1328(18) Uani 1 1 d . . . . .
F8 F 0.7763(4) 0.5246(3) 0.4418(2) 0.1078(14) Uani 1 1 d . . . . .
F9 F 0.2596(5) 0.5733(4) 0.4993(3) 0.1406(18) Uani 1 1 d . . . . .
F10 F 0.2087(6) 0.4312(5) 0.3998(4) 0.182(3) Uani 1 1 d . . . . .
F11 F 0.4777(8) 0.6382(5) 0.2557(3) 0.191(3) Uani 1 1 d . . . . .
F12 F 0.5334(7) 0.7781(5) 0.3543(3) 0.164(3) Uani 1 1 d . . . . .
N1 N 0.6852(5) 0.6064(4) 0.6376(2) 0.0674(14) Uani 1 1 d . . . . .
N2 N 0.5683(5) 0.6023(4) 0.5334(2) 0.0536(12) Uani 1 1 d . . . . .
N3 N 0.5670(5) 0.7654(4) 0.6002(2) 0.0597(13) Uani 1 1 d . . . . .
C1 C 0.6452(7) 0.7113(5) 0.6430(3) 0.0573(16) Uani 1 1 d . . . . .
C2 C 0.6434(7) 0.5580(5) 0.5815(3) 0.0613(17) Uani 1 1 d . . . . .
C3 C 0.5329(6) 0.7056(5) 0.5467(3) 0.0578(16) Uani 1 1 d . . . . .
C4 C 0.6524(7) 0.9146(5) 0.6983(3) 0.0618(17) Uani 1 1 d . . . . .
C5 C 0.5288(7) 0.9570(5) 0.7181(3) 0.0618(16) Uani 1 1 d . . . . .
C6 C 0.4960(7) 1.0638(5) 0.7048(3) 0.0658(17) Uani 1 1 d . . . . .
C7 C 0.5832(9) 1.1327(6) 0.6730(4) 0.087(2) Uani 1 1 d . . . . .
H7A H 0.5601 1.2060 0.6651 0.105 Uiso 1 1 calc R U . . .
C8 C 0.7044(9) 1.0926(6) 0.6530(4) 0.091(2) Uani 1 1 d . . . . .
C9 C 0.7394(9) 0.9838(6) 0.6651(3) 0.080(2) Uani 1 1 d . . . . .
C10 C 0.6426(6) 0.3884(5) 0.4928(3) 0.0606(16) Uani 1 1 d . . . . .
C11 C 0.5553(7) 0.3023(5) 0.4822(4) 0.0686(17) Uani 1 1 d . . . . .
C12 C 0.5181(7) 0.2720(5) 0.4190(5) 0.083(2) Uani 1 1 d . . . . .
C13 C 0.5641(8) 0.3258(6) 0.3648(4) 0.081(2) Uani 1 1 d . . . . .
H13A H 0.5391 0.3043 0.3220 0.098 Uiso 1 1 calc R U . . .
C14 C 0.6464(8) 0.4107(6) 0.3746(4) 0.078(2) Uani 1 1 d . . . . .
C15 C 0.6883(6) 0.4418(5) 0.4362(3) 0.0646(17) Uani 1 1 d . . . . .
C16 C 0.3966(7) 0.6796(6) 0.4291(4) 0.0741(19) Uani 1 1 d . . . . .
C17 C 0.3142(8) 0.5913(8) 0.4381(5) 0.095(2) Uani 1 1 d . . . . .
C18 C 0.2860(9) 0.5187(8) 0.3877(6) 0.109(3) Uani 1 1 d . . . . .
C19 C 0.3406(10) 0.5363(8) 0.3261(5) 0.111(3) Uani 1 1 d . . . . .
H19A H 0.3198 0.4886 0.2912 0.133 Uiso 1 1 calc R U . . .
C20 C 0.4248(11) 0.6223(8) 0.3152(5) 0.114(3) Uani 1 1 d . . . . .
C21 C 0.4532(10) 0.6933(7) 0.3668(5) 0.100(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.747(6) . ?
S1 C4 1.757(6) . ?
S2 C10 1.753(6) . ?
S2 C2 1.754(6) . ?
S3 C3 1.750(6) . ?
S3 C16 1.768(7) . ?
F1 C5 1.333(7) . ?
F2 C6 1.355(7) . ?
F3 C8 1.357(8) . ?
F4 C9 1.341(8) . ?
F5 C11 1.333(7) . ?
F6 C12 1.355(7) . ?
F7 C14 1.360(8) . ?
F8 C15 1.334(6) . ?
F9 C17 1.358(9) . ?
F10 C18 1.329(9) . ?
F11 C20 1.317(10) . ?
F12 C21 1.322(9) . ?
N1 C2 1.334(7) . ?
N1 C1 1.336(7) . ?
N2 C3 1.326(7) . ?
N2 C2 1.330(7) . ?
N3 C1 1.327(7) . ?
N3 C3 1.338(7) . ?
C4 C9 1.374(9) . ?
C4 C5 1.385(8) . ?
C5 C6 1.360(8) . ?
C6 C7 1.360(9) . ?
C7 C8 1.355(10) . ?
C7 H7A 0.9300 . ?
C8 C9 1.384(9) . ?
C10 C11 1.371(8) . ?
C10 C15 1.380(8) . ?
C11 C12 1.370(10) . ?
C12 C13 1.345(9) . ?
C13 C14 1.326(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.356(9) . ?
C16 C17 1.358(10) . ?
C16 C21 1.379(10) . ?
C17 C18 1.367(12) . ?
C18 C19 1.364(12) . ?
C19 C20 1.351(12) . ?
C19 H19A 0.9300 . ?
C20 C21 1.372(11) . ?

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 C4 100.9(3) . . ?
C10 S2 C2 101.5(3) . . ?
C3 S3 C16 101.9(3) . . ?
C2 N1 C1 113.2(5) . . ?
C3 N2 C2 112.5(5) . . ?
C1 N3 C3 113.4(5) . . ?
N3 C1 N1 126.2(5) . . ?
N3 C1 S1 119.3(4) . . ?
N1 C1 S1 114.5(5) . . ?
N2 C2 N1 127.3(5) . . ?
N2 C2 S2 119.4(5) . . ?
N1 C2 S2 113.3(5) . . ?
N2 C3 N3 127.3(5) . . ?
N2 C3 S3 120.6(5) . . ?
N3 C3 S3 112.1(4) . . ?
C9 C4 C5 117.8(6) . . ?
C9 C4 S1 120.5(6) . . ?
C5 C4 S1 121.7(6) . . ?
F1 C5 C6 118.5(6) . . ?
F1 C5 C4 121.0(6) . . ?
C6 C5 C4 120.5(6) . . ?
F2 C6 C5 119.7(6) . . ?
F2 C6 C7 118.7(6) . . ?
C5 C6 C7 121.6(7) . . ?
C8 C7 C6 118.7(7) . . ?
C8 C7 H7A 120.6 . . ?
C6 C7 H7A 120.6 . . ?
C7 C8 F3 121.3(7) . . ?
C7 C8 C9 120.8(7) . . ?
F3 C8 C9 117.9(8) . . ?
F4 C9 C4 120.1(7) . . ?
F4 C9 C8 119.2(8) . . ?
C4 C9 C8 120.6(7) . . ?
C11 C10 C15 115.9(6) . . ?
C11 C10 S2 121.5(5) . . ?
C15 C10 S2 122.5(5) . . ?
F5 C11 C12 119.4(6) . . ?
F5 C11 C10 119.6(6) . . ?
C12 C11 C10 121.0(7) . . ?
C13 C12 F6 120.3(8) . . ?
C13 C12 C11 121.7(6) . . ?
F6 C12 C11 118.0(8) . . ?
C14 C13 C12 117.7(7) . . ?
C14 C13 H13A 121.2 . . ?
C12 C13 H13A 121.2 . . ?
C13 C14 C15 122.5(7) . . ?
C13 C14 F7 118.9(7) . . ?
C15 C14 F7 118.6(7) . . ?
F8 C15 C14 119.0(7) . . ?
F8 C15 C10 119.8(6) . . ?
C14 C15 C10 121.1(6) . . ?
C17 C16 C21 117.3(8) . . ?
C17 C16 S3 122.8(7) . . ?
C21 C16 S3 119.8(7) . . ?
C16 C17 F9 119.0(9) . . ?
C16 C17 C18 122.2(9) . . ?
F9 C17 C18 118.8(9) . . ?
F10 C18 C19 121.2(10) . . ?
F10 C18 C17 119.7(11) . . ?
C19 C18 C17 119.1(9) . . ?
C20 C19 C18 120.7(10) . . ?
C20 C19 H19A 119.6 . . ?
C18 C19 H19A 119.6 . . ?
F11 C20 C19 120.3(10) . . ?
F11 C20 C21 120.5(10) . . ?
C19 C20 C21 119.2(10) . . ?
F12 C21 C20 117.9(9) . . ?
F12 C21 C16 120.5(8) . . ?
C20 C21 C16 121.5(8) . . ?

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
C3 N3 C1 N1 -2.6(9) . . . . ?
C3 N3 C1 S1 179.9(4) . . . . ?
C2 N1 C1 N3 2.8(9) . . . . ?
C2 N1 C1 S1 -179.6(5) . . . . ?
C4 S1 C1 N3 -11.4(6) . . . . ?
C4 S1 C1 N1 170.8(5) . . . . ?
C3 N2 C2 N1 -1.3(9) . . . . ?
C3 N2 C2 S2 -179.8(4) . . . . ?
C1 N1 C2 N2 -0.7(9) . . . . ?
C1 N1 C2 S2 177.9(5) . . . . ?
C10 S2 C2 N2 4.0(6) . . . . ?
C10 S2 C2 N1 -174.7(5) . . . . ?
C2 N2 C3 N3 1.6(9) . . . . ?
C2 N2 C3 S3 -177.0(4) . . . . ?
C1 N3 C3 N2 0.2(9) . . . . ?
C1 N3 C3 S3 178.8(4) . . . . ?
C16 S3 C3 N2 0.2(6) . . . . ?
C16 S3 C3 N3 -178.6(5) . . . . ?
C1 S1 C4 C9 -88.1(6) . . . . ?
C1 S1 C4 C5 92.7(5) . . . . ?
C9 C4 C5 F1 -179.2(6) . . . . ?
S1 C4 C5 F1 -0.1(8) . . . . ?
C9 C4 C5 C6 -0.1(9) . . . . ?
S1 C4 C5 C6 179.0(5) . . . . ?
F1 C5 C6 F2 -1.1(9) . . . . ?
C4 C5 C6 F2 179.7(5) . . . . ?
F1 C5 C6 C7 178.0(6) . . . . ?
C4 C5 C6 C7 -1.1(10) . . . . ?
F2 C6 C7 C8 -179.4(7) . . . . ?
C5 C6 C7 C8 1.4(11) . . . . ?
C6 C7 C8 F3 179.5(7) . . . . ?
C6 C7 C8 C9 -0.5(12) . . . . ?
C5 C4 C9 F4 178.1(6) . . . . ?
S1 C4 C9 F4 -1.1(9) . . . . ?
C5 C4 C9 C8 1.0(10) . . . . ?
S1 C4 C9 C8 -178.1(6) . . . . ?
C7 C8 C9 F4 -177.8(7) . . . . ?
F3 C8 C9 F4 2.2(11) . . . . ?
C7 C8 C9 C4 -0.8(12) . . . . ?
F3 C8 C9 C4 179.3(7) . . . . ?
C2 S2 C10 C11 -120.4(5) . . . . ?
C2 S2 C10 C15 64.0(5) . . . . ?
C15 C10 C11 F5 179.4(6) . . . . ?
S2 C10 C11 F5 3.5(8) . . . . ?
C15 C10 C11 C12 0.6(9) . . . . ?
S2 C10 C11 C12 -175.3(5) . . . . ?
F5 C11 C12 C13 -179.6(7) . . . . ?
C10 C11 C12 C13 -0.7(11) . . . . ?
F5 C11 C12 F6 -0.2(10) . . . . ?
C10 C11 C12 F6 178.6(6) . . . . ?
F6 C12 C13 C14 180.0(6) . . . . ?
C11 C12 C13 C14 -0.7(11) . . . . ?
C12 C13 C14 C15 2.2(11) . . . . ?
C12 C13 C14 F7 -179.2(7) . . . . ?
C13 C14 C15 F8 176.7(6) . . . . ?
F7 C14 C15 F8 -1.8(10) . . . . ?
C13 C14 C15 C10 -2.4(11) . . . . ?
F7 C14 C15 C10 179.0(6) . . . . ?
C11 C10 C15 F8 -178.2(5) . . . . ?
S2 C10 C15 F8 -2.4(8) . . . . ?
C11 C10 C15 C14 0.9(9) . . . . ?
S2 C10 C15 C14 176.8(5) . . . . ?
C3 S3 C16 C17 73.6(6) . . . . ?
C3 S3 C16 C21 -109.2(6) . . . . ?
C21 C16 C17 F9 178.2(7) . . . . ?
S3 C16 C17 F9 -4.5(10) . . . . ?
C21 C16 C17 C18 -0.8(11) . . . . ?
S3 C16 C17 C18 176.5(6) . . . . ?
C16 C17 C18 F10 177.4(7) . . . . ?
F9 C17 C18 F10 -1.5(12) . . . . ?
C16 C17 C18 C19 -1.0(13) . . . . ?
F9 C17 C18 C19 -180.0(7) . . . . ?
F10 C18 C19 C20 -176.5(9) . . . . ?
C17 C18 C19 C20 1.9(14) . . . . ?
C18 C19 C20 F11 179.6(8) . . . . ?
C18 C19 C20 C21 -1.1(14) . . . . ?
F11 C20 C21 F12 0.9(14) . . . . ?
C19 C20 C21 F12 -178.5(9) . . . . ?
F11 C20 C21 C16 178.6(8) . . . . ?
C19 C20 C21 C16 -0.8(14) . . . . ?
C17 C16 C21 F12 179.3(7) . . . . ?
S3 C16 C21 F12 2.0(11) . . . . ?
C17 C16 C21 C20 1.7(12) . . . . ?
S3 C16 C21 C20 -175.7(6) . . . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.044

