# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_RAP122_0m
_database_code_depnum_ccdc_archive 'CCDC 1566076'
_audit_update_record             
;
2017-08-01 deposited with the CCDC.
2017-10-13 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         'C12 H6 S3, C6 H14 O2'
_chemical_formula_sum            'C18 H6 Cl4 O2 S3'
_chemical_formula_weight         492.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   14.6914(5)
_cell_length_b                   8.1203(3)
_cell_length_c                   16.3822(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.381(1)
_cell_angle_gamma                90
_cell_volume                     1854.66(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.8424
_cell_measurement_theta_max      74.6922
_cell_measurement_temperature    150(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'intense orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.119
_exptl_absorpt_coefficient_mu    9.080
_shelx_estimated_absorpt_T_min   0.222
_shelx_estimated_absorpt_T_max   0.411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.29
_exptl_absorpt_correction_T_max  0.41

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            13630
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -17
_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       19
_diffrn_reflns_theta_min         3.170
_diffrn_reflns_theta_max         74.683
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3660
_reflns_number_gt                3480
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT  (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL 2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_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. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 Å) and included 
as riding contributions with isotropic displacement parameters 1.2  
times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+2.6854P] 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         3660
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.53198(4) 0.19221(7) 0.39646(4) 0.02643(16) Uani 1 1 d . . . . .
Cl2 Cl 0.41062(5) 0.49883(8) 0.29898(4) 0.03107(17) Uani 1 1 d . . . . .
O1 O 0.60581(14) 0.2488(2) 0.58107(13) 0.0291(4) Uani 1 1 d . . . . .
C1 C 0.55672(17) 0.3617(3) 0.54418(17) 0.0201(5) Uani 1 1 d . . . . .
C2 C 0.51218(17) 0.3623(3) 0.44900(17) 0.0194(5) Uani 1 1 d . . . . .
C3 C 0.46043(17) 0.4908(3) 0.40785(16) 0.0202(5) Uani 1 1 d . . . . .
S1 S 0.14833(5) 0.59497(8) 0.30410(4) 0.02452(16) Uani 1 1 d . . . . .
S2 S 0.23309(4) 0.76115(7) 0.63845(4) 0.02157(15) Uani 1 1 d . . . . .
S3 S 0.34504(5) 0.17282(8) 0.55082(5) 0.02833(17) Uani 1 1 d . . . . .
C7 C 0.20157(16) 0.5359(3) 0.40958(15) 0.0157(4) Uani 1 1 d . . . . .
C8 C 0.19485(16) 0.6598(3) 0.46700(15) 0.0152(4) Uani 1 1 d . . . . .
C9 C 0.23486(16) 0.6292(3) 0.55645(15) 0.0156(4) Uani 1 1 d . . . . .
C10 C 0.28212(16) 0.4823(3) 0.58802(15) 0.0169(5) Uani 1 1 d . . . . .
C11 C 0.28947(16) 0.3616(3) 0.52757(16) 0.0173(5) Uani 1 1 d . . . . .
C12 C 0.24919(16) 0.3842(3) 0.43880(16) 0.0165(5) Uani 1 1 d . . . . .
C13 C 0.1182(2) 0.7836(3) 0.33571(18) 0.0251(5) Uani 1 1 d . . . . .
H13 H 0.0850 0.8652 0.2959 0.030 Uiso 1 1 calc R U . . .
C14 C 0.14599(16) 0.8069(3) 0.42318(16) 0.0169(5) Uani 1 1 d . . . . .
H14 H 0.1350 0.9041 0.4510 0.020 Uiso 1 1 calc R U . . .
C15 C 0.29430(19) 0.6210(3) 0.71470(17) 0.0249(5) Uani 1 1 d . . . . .
H15 H 0.3110 0.6418 0.7747 0.030 Uiso 1 1 calc R U . . .
C16 C 0.31722(17) 0.4766(3) 0.68210(17) 0.0234(5) Uani 1 1 d . . . . .
H16 H 0.3507 0.3868 0.7155 0.028 Uiso 1 1 calc R U . . .
C17 C 0.31375(19) 0.1219(3) 0.4439(2) 0.0287(6) Uani 1 1 d . . . . .
H17 H 0.3300 0.0191 0.4245 0.034 Uiso 1 1 calc R U . . .
C18 C 0.26328(17) 0.2416(3) 0.38849(18) 0.0194(5) Uani 1 1 d . . . . .
H18 H 0.2411 0.2336 0.3275 0.023 Uiso 1 1 calc R U . . .
Cl3 Cl 0.10138(4) 0.17224(7) 0.58358(4) 0.02318(15) Uani 1 1 d . . . . .
Cl4 Cl 0.02441(4) 0.21380(7) 0.37977(4) 0.02190(15) Uani 1 1 d . . . . .
O2 O 0.06523(13) 0.4655(2) 0.67018(11) 0.0241(4) Uani 1 1 d . . . . .
C4 C 0.03560(17) 0.4812(3) 0.59335(16) 0.0183(5) Uani 1 1 d . . . . .
C5 C 0.04611(16) 0.3468(3) 0.53419(16) 0.0172(5) Uani 1 1 d . . . . .
C6 C 0.01357(16) 0.3645(3) 0.44862(16) 0.0167(5) 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
Cl1 C2 1.700(2) . ?
Cl2 C3 1.702(3) . ?
O1 C1 1.205(3) . ?
C1 C2 1.489(4) . ?
C1 C3 1.497(3) 3_666 ?
C2 C3 1.341(3) . ?
C3 C1 1.497(3) 3_666 ?
S1 C13 1.719(3) . ?
S1 C7 1.725(2) . ?
S2 C15 1.719(3) . ?
S2 C9 1.725(2) . ?
S3 C17 1.715(3) . ?
S3 C11 1.722(2) . ?
C7 C8 1.402(3) . ?
C7 C12 1.423(3) . ?
C8 C9 1.418(3) . ?
C8 C14 1.460(3) . ?
C9 C10 1.395(3) . ?
C10 C11 1.422(3) . ?
C10 C16 1.464(3) . ?
C11 C12 1.399(4) . ?
C12 C18 1.474(3) . ?
C13 C14 1.374(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.377(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
Cl3 C5 1.706(2) . ?
Cl4 C6 1.705(2) . ?
O2 C4 1.202(3) . ?
C4 C5 1.499(3) . ?
C4 C6 1.500(3) 3_566 ?
C5 C6 1.338(4) . ?
C6 C4 1.501(3) 3_566 ?

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
O1 C1 C2 121.6(2) . . ?
O1 C1 C3 121.3(2) . 3_666 ?
C2 C1 C3 117.2(2) . 3_666 ?
C3 C2 C1 121.4(2) . . ?
C3 C2 Cl1 122.5(2) . . ?
C1 C2 Cl1 116.05(18) . . ?
C2 C3 C1 121.4(2) . 3_666 ?
C2 C3 Cl2 123.0(2) . . ?
C1 C3 Cl2 115.56(18) 3_666 . ?
C13 S1 C7 91.40(12) . . ?
C15 S2 C9 91.25(12) . . ?
C17 S3 C11 91.90(13) . . ?
C8 C7 C12 121.8(2) . . ?
C8 C7 S1 111.54(17) . . ?
C12 C7 S1 126.66(18) . . ?
C7 C8 C9 118.3(2) . . ?
C7 C8 C14 112.6(2) . . ?
C9 C8 C14 129.1(2) . . ?
C10 C9 C8 121.9(2) . . ?
C10 C9 S2 111.74(18) . . ?
C8 C9 S2 126.34(18) . . ?
C9 C10 C11 118.0(2) . . ?
C9 C10 C16 112.8(2) . . ?
C11 C10 C16 129.2(2) . . ?
C12 C11 C10 122.2(2) . . ?
C12 C11 S3 111.26(17) . . ?
C10 C11 S3 126.48(19) . . ?
C11 C12 C7 117.7(2) . . ?
C11 C12 C18 113.0(2) . . ?
C7 C12 C18 129.3(2) . . ?
C14 C13 S1 114.63(19) . . ?
C14 C13 H13 122.7 . . ?
S1 C13 H13 122.7 . . ?
C13 C14 C8 109.8(2) . . ?
C13 C14 H14 125.1 . . ?
C8 C14 H14 125.1 . . ?
C16 C15 S2 114.8(2) . . ?
C16 C15 H15 122.6 . . ?
S2 C15 H15 122.6 . . ?
C15 C16 C10 109.5(2) . . ?
C15 C16 H16 125.2 . . ?
C10 C16 H16 125.2 . . ?
C18 C17 S3 114.72(19) . . ?
C18 C17 H17 122.6 . . ?
S3 C17 H17 122.6 . . ?
C17 C18 C12 109.1(2) . . ?
C17 C18 H18 125.4 . . ?
C12 C18 H18 125.4 . . ?
O2 C4 C5 121.5(2) . . ?
O2 C4 C6 122.1(2) . 3_566 ?
C5 C4 C6 116.4(2) . 3_566 ?
C6 C5 C4 121.5(2) . . ?
C6 C5 Cl3 123.05(19) . . ?
C4 C5 Cl3 115.40(18) . . ?
C5 C6 C4 122.1(2) . 3_566 ?
C5 C6 Cl4 122.59(19) . . ?
C4 C6 Cl4 115.34(18) 3_566 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.6(2) . . . . ?
C3 C1 C2 C3 1.2(4) 3_666 . . . ?
O1 C1 C2 Cl1 1.8(3) . . . . ?
C3 C1 C2 Cl1 -179.37(17) 3_666 . . . ?
C1 C2 C3 C1 -1.3(4) . . . 3_666 ?
Cl1 C2 C3 C1 179.36(18) . . . 3_666 ?
C1 C2 C3 Cl2 178.39(18) . . . . ?
Cl1 C2 C3 Cl2 -1.0(3) . . . . ?
C13 S1 C7 C8 0.51(18) . . . . ?
C13 S1 C7 C12 -178.2(2) . . . . ?
C12 C7 C8 C9 -1.7(3) . . . . ?
S1 C7 C8 C9 179.56(17) . . . . ?
C12 C7 C8 C14 178.0(2) . . . . ?
S1 C7 C8 C14 -0.7(2) . . . . ?
C7 C8 C9 C10 1.6(3) . . . . ?
C14 C8 C9 C10 -178.0(2) . . . . ?
C7 C8 C9 S2 -178.69(17) . . . . ?
C14 C8 C9 S2 1.7(4) . . . . ?
C15 S2 C9 C10 -0.40(18) . . . . ?
C15 S2 C9 C8 179.9(2) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
S2 C9 C10 C11 -179.78(17) . . . . ?
C8 C9 C10 C16 -179.7(2) . . . . ?
S2 C9 C10 C16 0.6(3) . . . . ?
C9 C10 C11 C12 -1.6(3) . . . . ?
C16 C10 C11 C12 178.0(2) . . . . ?
C9 C10 C11 S3 179.38(17) . . . . ?
C16 C10 C11 S3 -1.0(4) . . . . ?
C17 S3 C11 C12 -0.90(19) . . . . ?
C17 S3 C11 C10 178.2(2) . . . . ?
C10 C11 C12 C7 1.5(3) . . . . ?
S3 C11 C12 C7 -179.30(16) . . . . ?
C10 C11 C12 C18 -178.4(2) . . . . ?
S3 C11 C12 C18 0.8(3) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
S1 C7 C12 C11 178.72(18) . . . . ?
C8 C7 C12 C18 -179.9(2) . . . . ?
S1 C7 C12 C18 -1.3(4) . . . . ?
C7 S1 C13 C14 -0.1(2) . . . . ?
S1 C13 C14 C8 -0.2(3) . . . . ?
C7 C8 C14 C13 0.6(3) . . . . ?
C9 C8 C14 C13 -179.7(2) . . . . ?
C9 S2 C15 C16 0.1(2) . . . . ?
S2 C15 C16 C10 0.2(3) . . . . ?
C9 C10 C16 C15 -0.5(3) . . . . ?
C11 C10 C16 C15 179.9(2) . . . . ?
C11 S3 C17 C18 0.9(2) . . . . ?
S3 C17 C18 C12 -0.6(3) . . . . ?
C11 C12 C18 C17 -0.1(3) . . . . ?
C7 C12 C18 C17 179.9(2) . . . . ?
O2 C4 C5 C6 -179.6(2) . . . . ?
C6 C4 C5 C6 0.2(4) 3_566 . . . ?
O2 C4 C5 Cl3 0.6(3) . . . . ?
C6 C4 C5 Cl3 -179.50(16) 3_566 . . . ?
C4 C5 C6 C4 -0.2(4) . . . 3_566 ?
Cl3 C5 C6 C4 179.46(17) . . . 3_566 ?
C4 C5 C6 Cl4 -179.94(17) . . . . ?
Cl3 C5 C6 Cl4 -0.2(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
C13 H13 O2 0.95 2.42 3.283(3) 151.7 4_575
C15 H15 O1 0.95 2.45 3.366(3) 161.4 2_656
C17 H17 O1 0.95 2.38 3.306(3) 163.4 3_656

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.094

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_RAP115_0m
_database_code_depnum_ccdc_archive 'CCDC 1566077'
_audit_update_record             
;
2017-08-01 deposited with the CCDC.
2017-10-13 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         'C12 H4 N4, C12 H6 S3, C7 H8'
_chemical_formula_sum            'C31 H18 N4 S3'
_chemical_formula_weight         542.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   11.0658(3)
_cell_length_b                   11.3445(3)
_cell_length_c                   11.9815(3)
_cell_angle_alpha                67.768(1)
_cell_angle_beta                 73.706(1)
_cell_angle_gamma                88.504(1)
_cell_volume                     1330.94(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      4.1685
_cell_measurement_theta_max      72.1573
_cell_measurement_temperature    150(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark yellow-brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   0.650
_exptl_transmission_factor_max   0.806
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.017
_exptl_absorpt_coefficient_mu    2.765
_shelx_estimated_absorpt_T_min   0.500
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.95

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            18485
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.168
_diffrn_reflns_theta_max         72.236
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             5135
_reflns_number_gt                4279
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT  (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL 2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_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. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.98 Å) and included 
as riding contributions with isotropic displacement parameters 1.2 - 1.5 
times those of the attached atoms. The reflections 1 0 7, -1 -6 5, -2 -5 6, 
-3 -6 5 and 0 -8 5 were omitted from the final refinement as they appeared 
very close to the edges of the frames on which they were measured and so 
were considered to not be accurately determined.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0769P)²+3.0376P] 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         5135
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1763
_refine_ls_wR_factor_gt          0.1630
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
N1 N 0.6033(4) 0.9432(3) 0.8451(4) 0.0476(9) Uani 1 1 d . . . . .
N2 N 0.4484(4) 0.7949(3) 0.6200(3) 0.0469(9) Uani 1 1 d . . . . .
C1 C 0.5441(3) 0.4818(3) 1.1044(3) 0.0238(6) Uani 1 1 d . . . . .
H1 H 0.5739 0.4681 1.1750 0.029 Uiso 1 1 calc R U . . .
C2 C 0.5480(3) 0.6019(3) 1.0192(3) 0.0250(7) Uani 1 1 d . . . . .
H2 H 0.5799 0.6718 1.0312 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5048(3) 0.6259(3) 0.9112(3) 0.0228(6) Uani 1 1 d . . . . .
C4 C 0.5119(3) 0.7486(3) 0.8230(3) 0.0277(7) Uani 1 1 d . . . . .
C5 C 0.5623(4) 0.8569(3) 0.8352(3) 0.0331(8) Uani 1 1 d . . . . .
C6 C 0.4754(3) 0.7747(3) 0.7105(3) 0.0324(8) Uani 1 1 d . . . . .
N3 N 0.7929(4) 0.4548(4) 0.2297(3) 0.0467(9) Uani 1 1 d . . . . .
N4 N 0.8474(3) 0.1031(3) 0.5375(3) 0.0432(8) Uani 1 1 d . . . . .
C7 C 1.0149(3) 0.6332(3) 0.4328(3) 0.0228(6) Uani 1 1 d . . . . .
H7 H 1.0253 0.7234 0.3887 0.027 Uiso 1 1 calc R U . . .
C8 C 0.9570(3) 0.5605(3) 0.3931(3) 0.0233(6) Uani 1 1 d . . . . .
H8 H 0.9280 0.5998 0.3211 0.028 Uiso 1 1 calc R U . . .
C9 C 0.9388(3) 0.4228(3) 0.4593(3) 0.0221(6) Uani 1 1 d . . . . .
C10 C 0.8783(3) 0.3482(3) 0.4197(3) 0.0264(7) Uani 1 1 d . . . . .
C11 C 0.8299(3) 0.4044(3) 0.3144(4) 0.0321(8) Uani 1 1 d . . . . .
C12 C 0.8596(3) 0.2120(3) 0.4841(3) 0.0308(7) Uani 1 1 d . . . . .
S1 S 0.74179(9) 0.16935(8) 0.96299(9) 0.0357(2) Uani 1 1 d . . . . .
S2 S 0.63136(9) 0.50300(9) 0.55175(9) 0.0348(2) Uani 1 1 d . . . . .
S3 S 0.86312(9) 0.67533(9) 0.80815(9) 0.0359(2) Uani 1 1 d . . . . .
C13 C 0.8025(3) 0.5427(3) 0.7980(3) 0.0242(6) Uani 1 1 d . . . . .
C14 C 0.7957(3) 0.4128(3) 0.8784(3) 0.0231(6) Uani 1 1 d . . . . .
C15 C 0.7405(3) 0.3207(3) 0.8516(3) 0.0229(6) Uani 1 1 d . . . . .
C16 C 0.6933(3) 0.3548(3) 0.7469(3) 0.0245(7) Uani 1 1 d . . . . .
C17 C 0.7005(3) 0.4841(3) 0.6701(3) 0.0255(7) Uani 1 1 d . . . . .
C18 C 0.7565(3) 0.5803(3) 0.6931(3) 0.0255(7) Uani 1 1 d . . . . .
C19 C 0.8365(3) 0.3495(4) 0.9942(3) 0.0313(8) Uani 1 1 d . . . . .
H19 H 0.8759 0.3953 1.0284 0.038 Uiso 1 1 calc R U . . .
C20 C 0.8145(4) 0.2324(5) 1.0413(4) 0.0446(10) Uani 1 1 d . . . . .
H20 H 0.8358 0.1804 1.1152 0.054 Uiso 1 1 calc R U . . .
C21 C 0.6327(3) 0.2775(3) 0.6997(4) 0.0301(8) Uani 1 1 d . . . . .
H21 H 0.6205 0.1868 0.7383 0.036 Uiso 1 1 calc R U . . .
C22 C 0.5992(4) 0.3390(4) 0.6068(4) 0.0414(9) Uani 1 1 d . . . . .
H22 H 0.5585 0.2999 0.5679 0.050 Uiso 1 1 calc R U . . .
C23 C 0.7754(3) 0.7187(3) 0.6234(3) 0.0344(9) Uani 1 1 d . . . . .
H23 H 0.7505 0.7608 0.5492 0.041 Uiso 1 1 calc R U . . .
C24 C 0.8255(3) 0.7746(3) 0.6691(4) 0.0389(10) Uani 1 1 d . . . . .
H24 H 0.8435 0.8649 0.6334 0.047 Uiso 1 1 calc R U . . .
C25 C 0.8966(4) -0.0162(4) 0.3101(4) 0.0437(9) Uani 1 1 d . . . . .
H25 H 0.9348 0.0219 0.3516 0.052 Uiso 1 1 calc R U . . .
C26 C 0.9711(4) -0.0538(4) 0.2190(4) 0.0428(9) Uani 1 1 d . . . . .
H26 H 1.0605 -0.0406 0.1962 0.051 Uiso 1 1 calc R U . . .
C27 C 0.9152(4) -0.1105(4) 0.1611(4) 0.0393(9) Uani 1 1 d . . . . .
H27 H 0.9676 -0.1360 0.0980 0.047 Uiso 1 1 calc R U . . .
C28 C 0.7861(4) -0.1321(4) 0.1910(4) 0.0415(9) Uani 1 1 d . . . . .
C29 C 0.7106(4) -0.0900(4) 0.2837(4) 0.0455(10) Uani 1 1 d . . . . .
H29 H 0.6210 -0.1009 0.3055 0.055 Uiso 1 1 calc R U . . .
C30 C 0.7670(4) -0.0334(3) 0.3419(3) 0.0388(9) Uani 1 1 d . . . . .
H30 H 0.7162 -0.0061 0.4043 0.047 Uiso 1 1 calc R U . . .
C31 C 0.7251(6) -0.1934(6) 0.1270(6) 0.0679(14) Uani 1 1 d . . . . .
H31A H 0.6618 -0.1395 0.0951 0.102 Uiso 1 1 calc R U . . .
H31B H 0.6839 -0.2777 0.1874 0.102 Uiso 1 1 calc R U . . .
H31C H 0.7896 -0.2030 0.0566 0.102 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
N1 C5 1.149(5) . ?
N2 C6 1.143(5) . ?
C1 C2 1.352(5) . ?
C1 C3 1.444(4) 2_667 ?
C1 H1 0.9500 . ?
C2 C3 1.432(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(5) . ?
C3 C1 1.444(4) 2_667 ?
C4 C5 1.435(5) . ?
C4 C6 1.438(5) . ?
N3 C11 1.143(5) . ?
N4 C12 1.147(5) . ?
C7 C8 1.346(4) . ?
C7 C9 1.439(4) 2_766 ?
C7 H7 0.9500 . ?
C8 C9 1.449(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(4) . ?
C9 C7 1.439(4) 2_766 ?
C10 C11 1.428(5) . ?
C10 C12 1.432(5) . ?
S1 C20 1.732(5) . ?
S1 C15 1.733(3) . ?
S2 C22 1.731(4) . ?
S2 C17 1.736(3) . ?
S3 C13 1.722(3) . ?
S3 C24 1.778(4) . ?
C13 C18 1.401(5) . ?
C13 C14 1.414(4) . ?
C14 C15 1.402(4) . ?
C14 C19 1.492(4) . ?
C15 C16 1.409(5) . ?
C16 C17 1.396(5) . ?
C16 C21 1.469(4) . ?
C17 C18 1.417(5) . ?
C18 C23 1.461(5) . ?
C19 C20 1.231(6) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.221(6) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.209(6) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.372(6) . ?
C25 C30 1.376(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.369(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.376(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.422(6) . ?
C28 C31 1.499(6) . ?
C29 C30 1.374(6) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 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
C2 C1 C3 120.4(3) . 2_667 ?
C2 C1 H1 119.8 . . ?
C3 C1 H1 119.8 2_667 . ?
C1 C2 C3 121.3(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 C1 120.8(3) . 2_667 ?
C2 C3 C1 118.3(3) . 2_667 ?
C3 C4 C5 121.9(3) . . ?
C3 C4 C6 122.0(3) . . ?
C5 C4 C6 116.0(3) . . ?
N1 C5 C4 179.5(4) . . ?
N2 C6 C4 178.8(4) . . ?
C8 C7 C9 121.4(3) . 2_766 ?
C8 C7 H7 119.3 . . ?
C9 C7 H7 119.3 2_766 . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C7 121.3(3) . 2_766 ?
C10 C9 C8 120.6(3) . . ?
C7 C9 C8 118.1(3) 2_766 . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 C12 121.3(3) . . ?
C11 C10 C12 117.7(3) . . ?
N3 C11 C10 176.9(4) . . ?
N4 C12 C10 177.8(4) . . ?
C20 S1 C15 91.10(19) . . ?
C22 S2 C17 90.47(19) . . ?
C13 S3 C24 89.83(18) . . ?
C18 C13 C14 121.6(3) . . ?
C18 C13 S3 109.8(2) . . ?
C14 C13 S3 128.7(3) . . ?
C15 C14 C13 118.4(3) . . ?
C15 C14 C19 109.9(3) . . ?
C13 C14 C19 131.7(3) . . ?
C14 C15 C16 121.7(3) . . ?
C14 C15 S1 110.0(2) . . ?
C16 C15 S1 128.3(3) . . ?
C17 C16 C15 118.4(3) . . ?
C17 C16 C21 109.8(3) . . ?
C15 C16 C21 131.7(3) . . ?
C16 C17 C18 121.8(3) . . ?
C16 C17 S2 110.1(2) . . ?
C18 C17 S2 128.1(3) . . ?
C13 C18 C17 118.1(3) . . ?
C13 C18 C23 111.7(3) . . ?
C17 C18 C23 130.1(3) . . ?
C20 C19 C14 113.8(3) . . ?
C20 C19 H19 123.1 . . ?
C14 C19 H19 123.1 . . ?
C19 C20 S1 115.1(3) . . ?
C19 C20 H20 122.5 . . ?
S1 C20 H20 122.5 . . ?
C22 C21 C16 114.7(3) . . ?
C22 C21 H21 122.7 . . ?
C16 C21 H21 122.7 . . ?
C21 C22 S2 114.9(3) . . ?
C21 C22 H22 122.6 . . ?
S2 C22 H22 122.6 . . ?
C24 C23 C18 113.6(3) . . ?
C24 C23 H23 123.2 . . ?
C18 C23 H23 123.2 . . ?
C23 C24 S3 115.0(3) . . ?
C23 C24 H24 122.5 . . ?
S3 C24 H24 122.5 . . ?
C26 C25 C30 120.4(4) . . ?
C26 C25 H25 119.8 . . ?
C30 C25 H25 119.8 . . ?
C27 C26 C25 119.4(4) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C28 122.5(4) . . ?
C26 C27 H27 118.7 . . ?
C28 C27 H27 118.7 . . ?
C27 C28 C29 117.2(4) . . ?
C27 C28 C31 122.5(4) . . ?
C29 C28 C31 120.3(4) . . ?
C30 C29 C28 120.1(4) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C25 120.3(4) . . ?
C29 C30 H30 119.8 . . ?
C25 C30 H30 119.8 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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 C1 C2 C3 -0.5(5) 2_667 . . . ?
C1 C2 C3 C4 -178.4(3) . . . . ?
C1 C2 C3 C1 0.5(5) . . . 2_667 ?
C2 C3 C4 C5 0.0(5) . . . . ?
C1 C3 C4 C5 -178.9(3) 2_667 . . . ?
C2 C3 C4 C6 176.7(3) . . . . ?
C1 C3 C4 C6 -2.1(5) 2_667 . . . ?
C9 C7 C8 C9 0.6(5) 2_766 . . . ?
C7 C8 C9 C10 179.2(3) . . . . ?
C7 C8 C9 C7 -0.5(5) . . . 2_766 ?
C7 C9 C10 C11 178.5(3) 2_766 . . . ?
C8 C9 C10 C11 -1.2(5) . . . . ?
C7 C9 C10 C12 -0.3(5) 2_766 . . . ?
C8 C9 C10 C12 180.0(3) . . . . ?
C24 S3 C13 C18 -0.8(2) . . . . ?
C24 S3 C13 C14 179.3(3) . . . . ?
C18 C13 C14 C15 -0.5(4) . . . . ?
S3 C13 C14 C15 179.4(2) . . . . ?
C18 C13 C14 C19 -179.6(3) . . . . ?
S3 C13 C14 C19 0.3(5) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C19 C14 C15 C16 179.9(3) . . . . ?
C13 C14 C15 S1 -179.6(2) . . . . ?
C19 C14 C15 S1 -0.3(3) . . . . ?
C20 S1 C15 C14 0.2(2) . . . . ?
C20 S1 C15 C16 -180.0(3) . . . . ?
C14 C15 C16 C17 -1.1(5) . . . . ?
S1 C15 C16 C17 179.0(2) . . . . ?
C14 C15 C16 C21 179.9(3) . . . . ?
S1 C15 C16 C21 0.0(5) . . . . ?
C15 C16 C17 C18 1.7(5) . . . . ?
C21 C16 C17 C18 -179.1(3) . . . . ?
C15 C16 C17 S2 -177.7(2) . . . . ?
C21 C16 C17 S2 1.6(3) . . . . ?
C22 S2 C17 C16 -1.2(3) . . . . ?
C22 S2 C17 C18 179.5(3) . . . . ?
C14 C13 C18 C17 1.0(5) . . . . ?
S3 C13 C18 C17 -178.9(2) . . . . ?
C14 C13 C18 C23 -179.2(3) . . . . ?
S3 C13 C18 C23 0.9(3) . . . . ?
C16 C17 C18 C13 -1.6(5) . . . . ?
S2 C17 C18 C13 177.6(2) . . . . ?
C16 C17 C18 C23 178.7(3) . . . . ?
S2 C17 C18 C23 -2.2(5) . . . . ?
C15 C14 C19 C20 0.2(4) . . . . ?
C13 C14 C19 C20 179.4(3) . . . . ?
C14 C19 C20 S1 -0.1(4) . . . . ?
C15 S1 C20 C19 0.0(3) . . . . ?
C17 C16 C21 C22 -1.2(4) . . . . ?
C15 C16 C21 C22 177.8(3) . . . . ?
C16 C21 C22 S2 0.3(4) . . . . ?
C17 S2 C22 C21 0.6(3) . . . . ?
C13 C18 C23 C24 -0.5(4) . . . . ?
C17 C18 C23 C24 179.2(3) . . . . ?
C18 C23 C24 S3 -0.1(4) . . . . ?
C13 S3 C24 C23 0.5(3) . . . . ?
C30 C25 C26 C27 -1.0(6) . . . . ?
C25 C26 C27 C28 -0.2(6) . . . . ?
C26 C27 C28 C29 1.5(6) . . . . ?
C26 C27 C28 C31 179.5(4) . . . . ?
C27 C28 C29 C30 -1.7(6) . . . . ?
C31 C28 C29 C30 -179.8(4) . . . . ?
C28 C29 C30 C25 0.5(6) . . . . ?
C26 C25 C30 C29 0.8(6) . . . . ?

_refine_diff_density_max         0.524
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.084

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
####################################################################### 
# 
# 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_RAP126_0m
_database_code_depnum_ccdc_archive 'CCDC 1566078'
_audit_update_record             
;
2017-08-01 deposited with the CCDC.
2017-10-13 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         'C12 H6 S3, 0.5(C6 F4 O2)'
_chemical_formula_sum            'C15 H6 F2 O S3'
_chemical_formula_weight         336.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   18.6662(5)
_cell_length_b                   15.1927(4)
_cell_length_c                   9.3307(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.403(1)
_cell_angle_gamma                90
_cell_volume                     2646.03(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9198
_cell_measurement_theta_min      3.7513
_cell_measurement_theta_max      72.4073
_cell_measurement_temperature    150(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   0.753
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.138
_exptl_absorpt_coefficient_mu    5.310
_shelx_estimated_absorpt_T_min   0.398
_shelx_estimated_absorpt_T_max   0.528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_T_max  0.53
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            10062
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.751
_diffrn_reflns_theta_max         72.400
_diffrn_reflns_theta_full        69.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2571
_reflns_number_gt                2479
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT  (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL 2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_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)+(0.0498P)²+2.1914P] 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         2571
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
F1 F 0.33440(5) 0.63445(5) 0.85088(9) 0.0227(2) Uani 1 1 d . . . . .
F2 F 0.34802(5) 0.81090(5) 0.80546(9) 0.0232(2) Uani 1 1 d . . . . .
O1 O 0.23534(5) 0.57682(7) 1.04146(11) 0.0217(2) Uani 1 1 d . . . . .
C1 C 0.24229(7) 0.65542(9) 1.02298(14) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.29444(8) 0.69256(9) 0.92135(15) 0.0174(3) Uani 1 1 d . . . . .
C3 C 0.30133(7) 0.77879(9) 0.89970(15) 0.0172(3) Uani 1 1 d . . . . .
C4 C 0.36739(10) 0.19318(11) 0.74577(19) 0.0183(3) Uani 0.8413(10) 1 d . . P A
1
C5 C 0.35984(10) 0.28541(11) 0.76546(18) 0.0177(3) Uani 0.8413(10) 1 d . . P A
1
C6 C 0.40288(10) 0.34169(11) 0.68436(19) 0.0180(3) Uani 0.8413(10) 1 d . . P A
1
C7 C 0.45339(10) 0.30898(11) 0.58393(19) 0.0178(3) Uani 0.8413(10) 1 d . . P A
1
C8 C 0.45958(10) 0.21781(12) 0.56865(19) 0.0179(3) Uani 0.8413(10) 1 d . . P A
1
C9 C 0.41681(9) 0.15840(11) 0.64850(19) 0.0180(3) Uani 0.8413(10) 1 d . . P A 1
S1 S 0.32122(2) 0.11044(3) 0.83314(5) 0.02311(14) Uani 0.8413(10) 1 d . . P A 1
S2 S 0.38667(3) 0.45067(3) 0.72548(5) 0.02318(14) Uani 0.8413(10) 1 d . . P A 1
S3 S 0.52292(2) 0.19063(3) 0.44197(5) 0.02260(14) Uani 0.8413(10) 1 d . . P A 1
C10 C 0.41522(19) 0.06487(17) 0.6466(3) 0.0239(6) Uani 0.8413(10) 1 d . . P A 1
H10 H 0.4447 0.0301 0.5864 0.029 Uiso 0.8413(10) 1 calc R U P A 1
C11 C 0.36722(12) 0.03048(13) 0.7395(2) 0.0275(4) Uani 0.8413(10) 1 d . . P A 1
H11 H 0.3597 -0.0309 0.7519 0.033 Uiso 0.8413(10) 1 calc R U P A 1
C12 C 0.3142(2) 0.33373(17) 0.8590(4) 0.0211(6) Uani 0.8413(10) 1 d . . P A 1
H12 H 0.2813 0.3065 0.9223 0.025 Uiso 0.8413(10) 1 calc R U P A 1
C13 C 0.32213(12) 0.42162(13) 0.8490(2) 0.0251(3) Uani 0.8413(10) 1 d . . P A 1
H13 H 0.2954 0.4629 0.9035 0.030 Uiso 0.8413(10) 1 calc R U P A 1
C14 C 0.50081(17) 0.35499(15) 0.4911(3) 0.0223(5) Uani 0.8413(10) 1 d . . P A 1
H14 H 0.5038 0.4173 0.4864 0.027 Uiso 0.8413(10) 1 calc R U P A 1
C15 C 0.54100(11) 0.30044(14) 0.4108(2) 0.0247(3) Uani 0.8413(10) 1 d . . P A 1
H15 H 0.5756 0.3203 0.3440 0.030 Uiso 0.8413(10) 1 calc R U P A 1
C24 C 0.42255(18) 0.16402(14) 0.6321(3) 0.0180(3) Uani 0.1587(10) 1 d G . P A 2
C25 C 0.46203(17) 0.22912(16) 0.5580(3) 0.0179(3) Uani 0.1587(10) 1 d G . P A 2
C26 C 0.44914(17) 0.31760(15) 0.5920(3) 0.0178(3) Uani 0.1587(10) 1 d G . P A 2
C27 C 0.39852(19) 0.34279(15) 0.6967(4) 0.0180(3) Uani 0.1587(10) 1 d G . P A 2
C28 C 0.3607(2) 0.27595(17) 0.7672(4) 0.0177(3) Uani 0.1587(10) 1 d G . P A 2
C29 C 0.37186(19) 0.18568(16) 0.7366(4) 0.0183(3) Uani 0.1587(10) 1 d G . P A 2
S4 S 0.4285(3) 0.05067(15) 0.6099(5) 0.0239(6) Uani 0.1587(10) 1 d G . P A 2
S5 S 0.5025(2) 0.38715(19) 0.4903(4) 0.0223(5) Uani 0.1587(10) 1 d G . P A 2
S6 S 0.3014(3) 0.3198(2) 0.8910(5) 0.0211(6) Uani 0.1587(10) 1 d G . P A 2
C30 C 0.3388(2) 0.10927(19) 0.7967(5) 0.02311(14) Uani 0.1587(10) 1 d G . P A 2
H30 H 0.3032 0.1115 0.8689 0.028 Uiso 0.1587(10) 1 calc R U P A 2
C31 C 0.3638(3) 0.03330(16) 0.7393(5) 0.0275(4) Uani 0.1587(10) 1 d G . P A 2
H31 H 0.3476 -0.0234 0.7671 0.033 Uiso 0.1587(10) 1 calc R U P A 2
C32 C 0.5153(2) 0.2197(2) 0.4495(4) 0.02260(14) Uani 0.1587(10) 1 d G . P A 2
H32 H 0.5308 0.1645 0.4132 0.027 Uiso 0.1587(10) 1 calc R U P A 2
C33 C 0.5412(2) 0.2982(2) 0.4040(5) 0.0247(3) Uani 0.1587(10) 1 d G . P A 2
H33 H 0.5769 0.3038 0.3324 0.030 Uiso 0.1587(10) 1 calc R U P A 2
C34 C 0.3783(3) 0.42861(16) 0.7451(5) 0.02318(14) Uani 0.1587(10) 1 d G . P A 2
H34 H 0.3984 0.4816 0.7092 0.028 Uiso 0.1587(10) 1 calc R U P A 2
C35 C 0.3274(3) 0.4261(2) 0.8480(6) 0.0251(3) Uani 0.1587(10) 1 d G . P A 2
H35 H 0.3080 0.4771 0.8918 0.030 Uiso 0.1587(10) 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
F1 C2 1.3324(15) . ?
F2 C3 1.3347(16) . ?
O1 C1 1.2136(18) . ?
C1 C2 1.4758(19) . ?
C1 C3 1.4802(18) 7_567 ?
C2 C3 1.332(2) . ?
C3 C1 1.4801(18) 7_567 ?
C4 C9 1.402(2) . ?
C4 C5 1.420(2) . ?
C4 S1 1.7313(18) . ?
C5 C6 1.399(2) . ?
C5 C12 1.427(3) . ?
C6 C7 1.424(2) . ?
C6 S2 1.7268(18) . ?
C7 C8 1.397(2) . ?
C7 C14 1.426(3) . ?
C8 C9 1.420(2) . ?
C8 S3 1.7279(18) . ?
C9 C10 1.421(3) . ?
S1 C11 1.728(2) . ?
S2 C13 1.730(2) . ?
S3 C15 1.727(2) . ?
C10 C11 1.356(3) . ?
C12 C13 1.347(3) . ?
C14 C15 1.349(3) . ?
C24 C29 1.4026 . ?
C24 C25 1.4167 . ?
C24 S4 1.7381 . ?
C25 C26 1.4024 . ?
C25 C32 1.4312 . ?
C26 C27 1.4165 . ?
C26 S5 1.7381 . ?
C27 C28 1.4027 . ?
C27 C34 1.4313 . ?
C28 C29 1.4163 . ?
C28 S6 1.7382 . ?
C29 C30 1.4313 . ?
S4 C31 1.7345 . ?
S5 C33 1.7344 . ?
S6 C35 1.7343 . ?
C30 C31 1.3565 . ?
C32 C33 1.3564 . ?
C34 C35 1.3565 . ?

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
O1 C1 C2 122.62(13) . . ?
O1 C1 C3 122.38(13) . 7_567 ?
C2 C1 C3 115.00(12) . 7_567 ?
C3 C2 F1 121.46(13) . . ?
C3 C2 C1 122.57(13) . . ?
F1 C2 C1 115.97(12) . . ?
C2 C3 F2 121.57(13) . . ?
C2 C3 C1 122.43(13) . 7_567 ?
F2 C3 C1 116.00(12) . 7_567 ?
C9 C4 C5 121.46(15) . . ?
C9 C4 S1 111.29(13) . . ?
C5 C4 S1 127.25(14) . . ?
C6 C5 C4 118.36(15) . . ?
C6 C5 C12 111.34(16) . . ?
C4 C5 C12 130.30(17) . . ?
C5 C6 C7 121.88(15) . . ?
C5 C6 S2 111.32(13) . . ?
C7 C6 S2 126.79(13) . . ?
C8 C7 C6 117.96(15) . . ?
C8 C7 C14 111.84(16) . . ?
C6 C7 C14 130.20(17) . . ?
C7 C8 C9 121.98(15) . . ?
C7 C8 S3 111.36(13) . . ?
C9 C8 S3 126.66(14) . . ?
C4 C9 C8 118.37(15) . . ?
C4 C9 C10 111.79(16) . . ?
C8 C9 C10 129.85(17) . . ?
C11 S1 C4 91.25(9) . . ?
C6 S2 C13 91.57(9) . . ?
C15 S3 C8 91.14(9) . . ?
C11 C10 C9 113.0(2) . . ?
C10 C11 S1 112.66(16) . . ?
C13 C12 C5 113.7(2) . . ?
C12 C13 S2 112.11(16) . . ?
C15 C14 C7 112.7(2) . . ?
C14 C15 S3 112.93(15) . . ?
C29 C24 C25 122.1 . . ?
C29 C24 S4 111.1 . . ?
C25 C24 S4 126.8 . . ?
C26 C25 C24 117.9 . . ?
C26 C25 C32 112.2 . . ?
C24 C25 C32 129.9 . . ?
C25 C26 C27 122.1 . . ?
C25 C26 S5 111.1 . . ?
C27 C26 S5 126.8 . . ?
C28 C27 C26 117.9 . . ?
C28 C27 C34 112.2 . . ?
C26 C27 C34 130.0 . . ?
C27 C28 C29 122.1 . . ?
C27 C28 S6 111.0 . . ?
C29 C28 S6 126.8 . . ?
C24 C29 C28 117.9 . . ?
C24 C29 C30 112.2 . . ?
C28 C29 C30 130.0 . . ?
C31 S4 C24 91.3 . . ?
C33 S5 C26 91.3 . . ?
C35 S6 C28 91.3 . . ?
C31 C30 C29 112.6 . . ?
C30 C31 S4 112.9 . . ?
C33 C32 C25 112.6 . . ?
C32 C33 S5 112.9 . . ?
C35 C34 C27 112.7 . . ?
C34 C35 S6 112.9 . . ?

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
O1 C1 C2 C3 179.05(14) . . . . ?
C3 C1 C2 C3 -0.6(2) 7_567 . . . ?
O1 C1 C2 F1 -0.5(2) . . . . ?
C3 C1 C2 F1 179.82(12) 7_567 . . . ?
F1 C2 C3 F2 0.7(2) . . . . ?
C1 C2 C3 F2 -178.85(13) . . . . ?
F1 C2 C3 C1 -179.80(13) . . . 7_567 ?
C1 C2 C3 C1 0.7(2) . . . 7_567 ?
C9 C4 C5 C6 0.4(2) . . . . ?
S1 C4 C5 C6 179.56(14) . . . . ?
C9 C4 C5 C12 -179.0(2) . . . . ?
S1 C4 C5 C12 0.2(3) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C12 C5 C6 C7 179.5(2) . . . . ?
C4 C5 C6 S2 -179.15(13) . . . . ?
C12 C5 C6 S2 0.3(2) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
S2 C6 C7 C8 178.49(13) . . . . ?
C5 C6 C7 C14 179.1(2) . . . . ?
S2 C6 C7 C14 -1.9(3) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C14 C7 C8 C9 -178.98(19) . . . . ?
C6 C7 C8 S3 179.72(13) . . . . ?
C14 C7 C8 S3 0.0(2) . . . . ?
C5 C4 C9 C8 -0.2(2) . . . . ?
S1 C4 C9 C8 -179.51(13) . . . . ?
C5 C4 C9 C10 179.94(19) . . . . ?
S1 C4 C9 C10 0.6(2) . . . . ?
C7 C8 C9 C4 -0.3(2) . . . . ?
S3 C8 C9 C4 -179.21(14) . . . . ?
C7 C8 C9 C10 179.5(2) . . . . ?
S3 C8 C9 C10 0.6(3) . . . . ?
C9 C4 S1 C11 -0.36(15) . . . . ?
C5 C4 S1 C11 -179.61(16) . . . . ?
C5 C6 S2 C13 -0.55(15) . . . . ?
C7 C6 S2 C13 -179.64(16) . . . . ?
C7 C8 S3 C15 0.23(14) . . . . ?
C9 C8 S3 C15 179.20(16) . . . . ?
C4 C9 C10 C11 -0.7(3) . . . . ?
C8 C9 C10 C11 179.51(19) . . . . ?
C9 C10 C11 S1 0.4(3) . . . . ?
C4 S1 C11 C10 -0.01(19) . . . . ?
C6 C5 C12 C13 0.1(3) . . . . ?
C4 C5 C12 C13 179.6(2) . . . . ?
C5 C12 C13 S2 -0.5(3) . . . . ?
C6 S2 C13 C12 0.6(2) . . . . ?
C8 C7 C14 C15 -0.4(3) . . . . ?
C6 C7 C14 C15 179.98(19) . . . . ?
C7 C14 C15 S3 0.6(3) . . . . ?
C8 S3 C15 C14 -0.47(18) . . . . ?
C29 C24 C25 C26 0.0 . . . . ?
S4 C24 C25 C26 -180.0 . . . . ?
C29 C24 C25 C32 180.0 . . . . ?
S4 C24 C25 C32 0.0 . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C32 C25 C26 C27 -180.0 . . . . ?
C24 C25 C26 S5 180.0 . . . . ?
C32 C25 C26 S5 0.0 . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
S5 C26 C27 C28 180.0 . . . . ?
C25 C26 C27 C34 -180.0 . . . . ?
S5 C26 C27 C34 0.0 . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C34 C27 C28 C29 180.0 . . . . ?
C26 C27 C28 S6 180.0 . . . . ?
C34 C27 C28 S6 0.0 . . . . ?
C25 C24 C29 C28 0.0 . . . . ?
S4 C24 C29 C28 180.0 . . . . ?
C25 C24 C29 C30 180.0 . . . . ?
S4 C24 C29 C30 0.0 . . . . ?
C27 C28 C29 C24 0.0 . . . . ?
S6 C28 C29 C24 180.0 . . . . ?
C27 C28 C29 C30 -180.0 . . . . ?
S6 C28 C29 C30 0.0 . . . . ?
C29 C24 S4 C31 0.0 . . . . ?
C25 C24 S4 C31 -180.0 . . . . ?
C25 C26 S5 C33 0.0 . . . . ?
C27 C26 S5 C33 180.0 . . . . ?
C27 C28 S6 C35 0.0 . . . . ?
C29 C28 S6 C35 180.0 . . . . ?
C24 C29 C30 C31 0.0 . . . . ?
C28 C29 C30 C31 180.0 . . . . ?
C29 C30 C31 S4 0.0 . . . . ?
C24 S4 C31 C30 0.0 . . . . ?
C26 C25 C32 C33 0.0 . . . . ?
C24 C25 C32 C33 -180.0 . . . . ?
C25 C32 C33 S5 0.0 . . . . ?
C26 S5 C33 C32 0.0 . . . . ?
C28 C27 C34 C35 0.0 . . . . ?
C26 C27 C34 C35 180.0 . . . . ?
C27 C34 C35 S6 0.0 . . . . ?
C28 S6 C35 C34 0.0 . . . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.059

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_rp118
_database_code_depnum_ccdc_archive 'CCDC 1566079'
_audit_update_record             
;
2017-08-01 deposited with the CCDC.
2017-10-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT214_rp118               
;
PROBLEM: Atom C7      (Anion/Solvent) ADP max/min Ratio          6.7 prolat
RESPONSE: The presence of a few highly elongated ellipsoids is a manifestation of the high degree of disorder in this structure, and cannot be remedied without employing very strong restraints.
;
_vrf_PLAT214_rp118_2             
;
PROBLEM: Atom C47     (Anion/Solvent) ADP max/min Ratio          6.7 prolat
RESPONSE: The presence of a few highly elongated ellipsoids is a manifestation of the high degree of disorder in this structure, and cannot be remedied without employing very strong restraints.
;
_vrf_PLAT340_rp118               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01433 Ang.
RESPONSE: The low bond precision is a manifestation of the high degree of disorder in the structure.
;
_vrf_PLAT915_rp118               
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         49 %
RESPONSE: We do not understand this alert; the Friedel Coverage is 99.6%.
;
# Added during the CSD deposition process: Tuesday 01 August 2017 10:00 PM
# 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         'C12 F4 N4, 2(C12 H6 S3)'
_chemical_formula_sum            'C36 H12 F4 N4 S6'
_chemical_formula_weight         768.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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, z+1/2'

_cell_length_a                   8.8270(3)
_cell_length_b                   10.6251(4)
_cell_length_c                   16.8178(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.973(2)
_cell_angle_gamma                90
_cell_volume                     1571.37(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8536
_cell_measurement_theta_min      5.0294
_cell_measurement_theta_max      72.2300
_cell_measurement_temperature    150(2)

_exptl_crystal_description       column
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   0.692
_exptl_transmission_factor_max   0.840
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    4.550
_shelx_estimated_absorpt_T_min   0.552
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.91

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            11869
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.161
_diffrn_reflns_theta_max         72.314
_diffrn_reflns_theta_full        72.300
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4606
_reflns_number_gt                4069
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT  (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL 2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0623P)²+7.2238P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4606
_refine_ls_number_parameters     367
_refine_ls_number_restraints     1022
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0795
_refine_ls_wR_factor_ref         0.1959
_refine_ls_wR_factor_gt          0.1869
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.058
_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
C1 C 0.6459(13) -0.1102(9) 0.0381(7) 0.0271(13) Uani 0.843(5) 1 d . U P A 1
C2 C 0.4946(13) -0.0726(9) 0.0475(6) 0.0262(13) Uani 0.843(5) 1 d . U P A 1
C3 C 0.4054(12) -0.0295(10) -0.0215(7) 0.0252(13) Uani 0.843(5) 1 d . U P A 1
C4 C 0.4601(12) -0.0286(9) -0.0978(6) 0.0226(13) Uani 0.843(5) 1 d . U P A 1
C5 C 0.6091(12) -0.0713(9) -0.1035(6) 0.0240(13) Uani 0.843(5) 1 d . U P A 1
C6 C 0.7064(12) -0.1129(9) -0.0364(7) 0.0252(13) Uani 0.843(5) 1 d . U P A 1
S1 S 0.7787(4) -0.1702(3) 0.1111(2) 0.0377(6) Uani 0.843(5) 1 d . U P A 1
S2 S 0.2247(3) 0.0054(3) 0.0010(2) 0.0351(6) Uani 0.843(5) 1 d . U P A 1
S3 S 0.6512(3) -0.0768(3) -0.20128(17) 0.0291(5) Uani 0.843(5) 1 d . U P A 1
C7 C 0.8631(11) -0.1589(8) -0.0339(6) 0.0170(14) Uani 0.843(5) 1 d . U P A 1
H7 H 0.9256 -0.1668 -0.0768 0.020 Uiso 0.843(5) 1 calc R U P A 1
C8 C 0.8995(17) -0.1890(15) 0.0479(10) 0.0375(18) Uani 0.843(5) 1 d . U P A 1
H8 H 0.9976 -0.2208 0.0649 0.045 Uiso 0.843(5) 1 calc R U P A 1
C9 C 0.4050(14) -0.0726(9) 0.1189(7) 0.0251(16) Uani 0.843(5) 1 d . U P A 1
H9 H 0.4412 -0.0960 0.1717 0.030 Uiso 0.843(5) 1 calc R U P A 1
C10 C 0.2744(16) -0.0363(12) 0.0965(8) 0.0310(18) Uani 0.843(5) 1 d . U P A 1
H10 H 0.2005 -0.0319 0.1342 0.037 Uiso 0.843(5) 1 calc R U P A 1
C11 C 0.3745(12) 0.0011(8) -0.1789(6) 0.0163(13) Uani 0.843(5) 1 d . U P A 1
H11 H 0.2722 0.0284 -0.1896 0.020 Uiso 0.843(5) 1 calc R U P A 1
C12 C 0.4813(13) -0.0212(10) -0.2328(7) 0.0296(15) Uani 0.843(5) 1 d . U P A 1
H12 H 0.4571 -0.0047 -0.2880 0.036 Uiso 0.843(5) 1 calc R U P A 1
C61 C 0.6964(16) -0.1183(15) 0.0111(10) 0.0327(18) Uani 0.157(5) 1 d G U P A 2
C62 C 0.6468(16) -0.0855(13) -0.0686(9) 0.0282(18) Uani 0.157(5) 1 d G U P A 2
C63 C 0.4980(16) -0.0399(11) -0.0840(8) 0.0256(18) Uani 0.157(5) 1 d G U P A 2
C64 C 0.3983(15) -0.0263(12) -0.0230(8) 0.0256(18) Uani 0.157(5) 1 d G U P A 2
C65 C 0.4526(16) -0.0601(13) 0.0549(8) 0.0278(18) Uani 0.157(5) 1 d G U P A 2
C66 C 0.6019(18) -0.1065(15) 0.0735(8) 0.0316(19) Uani 0.157(5) 1 d G U P A 2
S10 S 0.8740(19) -0.177(2) 0.0456(13) 0.0549(14) Uani 0.157(5) 1 d G U P A 2
S11 S 0.459(2) -0.0050(15) -0.1847(8) 0.0406(11) Uani 0.157(5) 1 d G U P A 2
S12 S 0.314(2) -0.0368(19) 0.1210(9) 0.0400(12) Uani 0.157(5) 1 d G U P A 2
C67 C 0.676(2) -0.145(2) 0.1485(9) 0.040(2) Uani 0.157(5) 1 d G U P A 2
H67 H 0.6294 -0.1436 0.1973 0.048 Uiso 0.157(5) 1 calc R U P A 2
C68 C 0.821(2) -0.185(2) 0.1424(12) 0.049(3) Uani 0.157(5) 1 d G U P A 2
H68 H 0.8865 -0.2134 0.1865 0.059 Uiso 0.157(5) 1 calc R U P A 2
C69 C 0.726(2) -0.0910(18) -0.1392(11) 0.031(2) Uani 0.157(5) 1 d G U P A 2
H69 H 0.8278 -0.1195 -0.1399 0.038 Uiso 0.157(5) 1 calc R U P A 2
C70 C 0.640(2) -0.0511(18) -0.2051(9) 0.036(2) Uani 0.157(5) 1 d G U P A 2
H70 H 0.6747 -0.0487 -0.2569 0.043 Uiso 0.157(5) 1 calc R U P A 2
C71 C 0.2447(15) 0.0179(17) -0.0273(10) 0.031(2) Uani 0.157(5) 1 d G U P A 2
H71 H 0.1896 0.0448 -0.0754 0.037 Uiso 0.157(5) 1 calc R U P A 2
C72 C 0.1862(17) 0.017(2) 0.0447(11) 0.037(2) Uani 0.157(5) 1 d G U P A 2
H72 H 0.0858 0.0437 0.0524 0.044 Uiso 0.157(5) 1 calc R U P A 2
C21 C 0.6885(4) 0.5238(3) 0.06156(19) 0.0256(18) Uani 0.567(4) 1 d G U P B 1
C22 C 0.7658(3) 0.5186(3) -0.00876(19) 0.0256(18) Uani 0.567(4) 1 d G U P B 1
C23 C 0.6866(4) 0.5566(3) -0.08064(19) 0.0278(18) Uani 0.567(4) 1 d G U P B 1
C24 C 0.5341(4) 0.5992(3) -0.0844(2) 0.0316(19) Uani 0.567(4) 1 d G U P B 1
C25 C 0.4624(4) 0.6027(3) -0.0132(2) 0.0327(18) Uani 0.567(4) 1 d G U P B 1
C26 C 0.5376(4) 0.5654(3) 0.0609(2) 0.0282(18) Uani 0.567(4) 1 d G U P B 1
S4 S 0.7608(5) 0.4823(5) 0.1574(2) 0.0406(11) Uani 0.567(4) 1 d G U P B 1
S5 S 0.7999(5) 0.5435(4) -0.1597(2) 0.0400(12) Uani 0.567(4) 1 d G U P B 1
S6 S 0.2768(4) 0.6574(5) -0.0299(3) 0.0549(14) Uani 0.567(4) 1 d G U P B 1
C27 C 0.4836(5) 0.5625(4) 0.1387(2) 0.031(2) Uani 0.567(4) 1 d G U P B 1
H27 H 0.3840 0.5874 0.1494 0.038 Uiso 0.567(4) 1 calc R U P B 1
C28 C 0.5902(6) 0.5204(5) 0.1954(2) 0.036(2) Uani 0.567(4) 1 d G U P B 1
H28 H 0.5731 0.5127 0.2502 0.043 Uiso 0.567(4) 1 calc R U P B 1
C29 C 0.9178(4) 0.4795(4) -0.0196(2) 0.031(2) Uani 0.567(4) 1 d G U P B 1
H29 H 0.9878 0.4508 0.0226 0.037 Uiso 0.567(4) 1 calc R U P B 1
C30 C 0.9510(4) 0.4878(5) -0.0967(3) 0.037(2) Uani 0.567(4) 1 d G U P B 1
H30 H 1.0469 0.4655 -0.1143 0.044 Uiso 0.567(4) 1 calc R U P B 1
C31 C 0.4361(5) 0.6412(4) -0.1514(2) 0.040(2) Uani 0.567(4) 1 d G U P B 1
H31 H 0.4657 0.6451 -0.2043 0.048 Uiso 0.567(4) 1 calc R U P B 1
C32 C 0.2963(5) 0.6750(5) -0.1311(3) 0.049(3) Uani 0.567(4) 1 d G U P B 1
H32 H 0.2175 0.7050 -0.1683 0.059 Uiso 0.567(4) 1 calc R U P B 1
C41 C 0.4988(4) 0.6090(4) -0.0738(2) 0.0271(13) Uani 0.433(4) 1 d G U P B 2
C42 C 0.6489(4) 0.5691(4) -0.0841(2) 0.0262(13) Uani 0.433(4) 1 d G U P B 2
C43 C 0.7409(4) 0.5313(4) -0.0161(2) 0.0252(13) Uani 0.433(4) 1 d G U P B 2
C44 C 0.6880(4) 0.5322(4) 0.0611(2) 0.0226(13) Uani 0.433(4) 1 d G U P B 2
C45 C 0.5384(4) 0.5725(4) 0.0682(2) 0.0240(13) Uani 0.433(4) 1 d G U P B 2
C46 C 0.4412(4) 0.6116(4) 0.0014(2) 0.0252(13) Uani 0.433(4) 1 d G U P B 2
S7 S 0.3631(5) 0.6600(5) -0.1479(2) 0.0377(6) Uani 0.433(4) 1 d G U P B 2
S8 S 0.9201(4) 0.4859(6) -0.0408(3) 0.0351(6) Uani 0.433(4) 1 d G U P B 2
S9 S 0.4949(6) 0.5670(5) 0.1670(2) 0.0291(5) Uani 0.433(4) 1 d G U P B 2
C47 C 0.2873(4) 0.6551(5) -0.0029(3) 0.0170(14) Uani 0.433(4) 1 d G U P B 2
H47 H 0.2302 0.6629 0.0422 0.020 Uiso 0.433(4) 1 calc R U P B 2
C48 C 0.2318(5) 0.6841(6) -0.0785(3) 0.0375(18) Uani 0.433(4) 1 d G U P B 2
H48 H 0.1315 0.7144 -0.0919 0.045 Uiso 0.433(4) 1 calc R U P B 2
C49 C 0.7265(6) 0.5603(5) -0.1552(2) 0.0251(16) Uani 0.433(4) 1 d G U P B 2
H49 H 0.6816 0.5820 -0.2067 0.030 Uiso 0.433(4) 1 calc R U P B 2
C50 C 0.8710(6) 0.5175(6) -0.1409(3) 0.0310(18) Uani 0.433(4) 1 d G U P B 2
H50 H 0.9383 0.5060 -0.1815 0.037 Uiso 0.433(4) 1 calc R U P B 2
C51 C 0.7643(5) 0.4975(5) 0.1364(2) 0.0163(13) Uani 0.433(4) 1 d G U P B 2
H51 H 0.8662 0.4679 0.1429 0.020 Uiso 0.433(4) 1 calc R U P B 2
C52 C 0.6752(6) 0.5113(6) 0.1976(2) 0.0296(15) Uani 0.433(4) 1 d G U P B 2
H52 H 0.7082 0.4925 0.2516 0.036 Uiso 0.433(4) 1 calc R U P B 2
F1 F 0.2849(6) 0.3303(5) -0.0282(4) 0.0278(7) Uani 1 1 d . . . . .
F2 F 0.4288(7) 0.3231(5) -0.1586(3) 0.0293(7) Uani 1 1 d . . . . .
N1 N 1.0090(13) 0.1644(11) -0.1671(7) 0.0486(14) Uani 1 1 d . . . . .
N2 N 0.6253(12) 0.2981(10) -0.3005(6) 0.0410(13) Uani 1 1 d . . . . .
C81 C 0.4267(12) 0.2883(8) -0.0222(6) 0.0221(10) Uani 1 1 d . . . . .
C82 C 0.4998(12) 0.2848(8) -0.0891(6) 0.0216(10) Uani 1 1 d . . . . .
C83 C 0.6553(11) 0.2398(8) -0.0884(6) 0.0208(10) Uani 1 1 d . . . . .
C84 C 0.7332(12) 0.2358(9) -0.1578(6) 0.0268(12) Uani 1 1 d . . . . .
C85 C 0.8863(13) 0.1929(10) -0.1599(7) 0.0333(13) Uani 1 1 d . . . . .
C86 C 0.6676(13) 0.2722(9) -0.2360(6) 0.0296(12) Uani 1 1 d . . . . .
F3 F 0.8655(6) 0.1568(5) -0.0067(4) 0.0278(7) Uani 1 1 d . . . . .
F4 F 0.7179(7) 0.1664(5) 0.1224(3) 0.0293(7) Uani 1 1 d . . . . .
N3 N 0.1415(12) 0.3262(12) 0.1322(7) 0.0486(14) Uani 1 1 d . . . . .
N4 N 0.5187(12) 0.1874(10) 0.2629(6) 0.0410(13) Uani 1 1 d . . . . .
C87 C 0.7218(12) 0.2004(8) -0.0125(6) 0.0221(10) Uani 1 1 d . . . . .
C88 C 0.6469(11) 0.2055(8) 0.0544(6) 0.0216(10) Uani 1 1 d . . . . .
C89 C 0.4945(11) 0.2487(8) 0.0557(6) 0.0208(10) Uani 1 1 d . . . . .
C90 C 0.4185(12) 0.2533(9) 0.1230(6) 0.0268(12) Uani 1 1 d . . . . .
C91 C 0.2627(14) 0.2932(10) 0.1231(7) 0.0333(13) Uani 1 1 d . . . . .
C92 C 0.4840(13) 0.2147(9) 0.1996(6) 0.0296(12) 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
C1 C6 1.403(16) . ?
C1 C2 1.416(16) . ?
C1 S1 1.744(11) . ?
C2 C3 1.420(16) . ?
C2 C9 1.494(14) . ?
C3 C4 1.410(14) . ?
C3 S2 1.712(11) . ?
C4 C5 1.402(14) . ?
C4 C11 1.533(15) . ?
C5 C6 1.428(15) . ?
C5 S3 1.718(11) . ?
C6 C7 1.464(14) . ?
S1 C8 1.582(17) . ?
S2 C10 1.687(15) . ?
S3 C12 1.656(12) . ?
C7 C8 1.422(18) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.24(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.384(14) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C61 C66 1.4024 . ?
C61 C62 1.4163 . ?
C61 S10 1.7380 . ?
C62 C63 1.4025 . ?
C62 C69 1.4310 . ?
C63 C64 1.4163 . ?
C63 S11 1.7389 . ?
C64 C65 1.4023 . ?
C64 C71 1.4307 . ?
C65 C66 1.4166 . ?
C65 S12 1.7380 . ?
C66 C67 1.4311 . ?
S10 C68 1.7345 . ?
S11 C70 1.7342 . ?
S12 C72 1.7341 . ?
C67 C68 1.3570 . ?
C67 H67 0.9500 . ?
C68 H68 0.9500 . ?
C69 C70 1.3569 . ?
C69 H69 0.9500 . ?
C70 H70 0.9500 . ?
C71 C72 1.3561 . ?
C71 H71 0.9500 . ?
C72 H72 0.9500 . ?
C21 C26 1.4026 . ?
C21 C22 1.4168 . ?
C21 S4 1.7375 . ?
C22 C23 1.4026 . ?
C22 C29 1.4309 . ?
C23 C24 1.4168 . ?
C23 S5 1.7380 . ?
C24 C25 1.4021 . ?
C24 C31 1.4307 . ?
C25 C26 1.4170 . ?
C25 S6 1.7383 . ?
C26 C27 1.4310 . ?
S4 C28 1.7347 . ?
S5 C30 1.7344 . ?
S6 C32 1.7349 . ?
C27 C28 1.3563 . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.3570 . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.3563 . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C41 C46 1.4030 . ?
C41 C42 1.4165 . ?
C41 S7 1.7380 . ?
C42 C43 1.4028 . ?
C42 C49 1.4307 . ?
C43 C44 1.4162 . ?
C43 S8 1.7385 . ?
C44 C45 1.4029 . ?
C44 C51 1.4315 . ?
C45 C46 1.4165 . ?
C45 S9 1.7379 . ?
C46 C47 1.4311 . ?
S7 C48 1.7341 . ?
S8 C50 1.7347 . ?
S9 C52 1.7343 . ?
C47 C48 1.3564 . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 C50 1.3565 . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C52 1.3563 . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
F1 C81 1.324(11) . ?
F2 C82 1.341(11) . ?
N1 C85 1.141(15) . ?
N2 C86 1.149(15) . ?
C81 C82 1.345(13) . ?
C81 C89 1.455(13) . ?
C82 C83 1.453(14) . ?
C83 C84 1.407(12) . ?
C83 C87 1.420(13) . ?
C84 C85 1.429(15) . ?
C84 C86 1.443(15) . ?
F3 C87 1.346(12) . ?
F4 C88 1.323(11) . ?
N3 C91 1.149(15) . ?
N4 C92 1.120(14) . ?
C87 C88 1.354(13) . ?
C88 C89 1.424(13) . ?
C89 C90 1.365(12) . ?
C90 C92 1.425(15) . ?
C90 C91 1.440(16) . ?

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
C6 C1 C2 122.8(10) . . ?
C6 C1 S1 109.6(9) . . ?
C2 C1 S1 127.4(9) . . ?
C1 C2 C3 117.4(10) . . ?
C1 C2 C9 131.3(10) . . ?
C3 C2 C9 111.3(10) . . ?
C4 C3 C2 122.5(10) . . ?
C4 C3 S2 126.8(9) . . ?
C2 C3 S2 110.5(8) . . ?
C5 C4 C3 117.2(10) . . ?
C5 C4 C11 113.5(9) . . ?
C3 C4 C11 129.0(9) . . ?
C4 C5 C6 123.3(10) . . ?
C4 C5 S3 111.0(8) . . ?
C6 C5 S3 125.5(8) . . ?
C1 C6 C5 116.7(10) . . ?
C1 C6 C7 114.4(10) . . ?
C5 C6 C7 128.9(10) . . ?
C8 S1 C1 91.4(6) . . ?
C10 S2 C3 89.1(6) . . ?
C12 S3 C5 91.7(5) . . ?
C8 C7 C6 103.7(10) . . ?
C8 C7 H7 128.2 . . ?
C6 C7 H7 128.2 . . ?
C7 C8 S1 120.8(11) . . ?
C7 C8 H8 119.6 . . ?
S1 C8 H8 119.6 . . ?
C10 C9 C2 107.3(11) . . ?
C10 C9 H9 126.3 . . ?
C2 C9 H9 126.3 . . ?
C9 C10 S2 121.8(9) . . ?
C9 C10 H10 119.1 . . ?
S2 C10 H10 119.1 . . ?
C12 C11 C4 103.6(10) . . ?
C12 C11 H11 128.2 . . ?
C4 C11 H11 128.2 . . ?
C11 C12 S3 120.0(10) . . ?
C11 C12 H12 120.0 . . ?
S3 C12 H12 120.0 . . ?
C66 C61 C62 122.1 . . ?
C66 C61 S10 111.0 . . ?
C62 C61 S10 126.9 . . ?
C63 C62 C61 117.9 . . ?
C63 C62 C69 112.2 . . ?
C61 C62 C69 129.9 . . ?
C62 C63 C64 122.1 . . ?
C62 C63 S11 111.0 . . ?
C64 C63 S11 126.8 . . ?
C65 C64 C63 117.9 . . ?
C65 C64 C71 112.2 . . ?
C63 C64 C71 130.0 . . ?
C64 C65 C66 122.1 . . ?
C64 C65 S12 111.0 . . ?
C66 C65 S12 126.8 . . ?
C61 C66 C65 117.9 . . ?
C61 C66 C67 112.2 . . ?
C65 C66 C67 129.9 . . ?
C68 S10 C61 91.3 . . ?
C70 S11 C63 91.3 . . ?
C72 S12 C65 91.3 . . ?
C68 C67 C66 112.6 . . ?
C68 C67 H67 123.7 . . ?
C66 C67 H67 123.7 . . ?
C67 C68 S10 112.8 . . ?
C67 C68 H68 123.6 . . ?
S10 C68 H68 123.6 . . ?
C70 C69 C62 112.7 . . ?
C70 C69 H69 123.7 . . ?
C62 C69 H69 123.7 . . ?
C69 C70 S11 112.8 . . ?
C69 C70 H70 123.6 . . ?
S11 C70 H70 123.6 . . ?
C72 C71 C64 112.6 . . ?
C72 C71 H71 123.7 . . ?
C64 C71 H71 123.7 . . ?
C71 C72 S12 112.9 . . ?
C71 C72 H72 123.6 . . ?
S12 C72 H72 123.6 . . ?
C26 C21 C22 122.1 . . ?
C26 C21 S4 111.1 . . ?
C22 C21 S4 126.8 . . ?
C23 C22 C21 117.9 . . ?
C23 C22 C29 112.2 . . ?
C21 C22 C29 130.0 . . ?
C22 C23 C24 122.1 . . ?
C22 C23 S5 111.1 . . ?
C24 C23 S5 126.8 . . ?
C25 C24 C23 117.9 . . ?
C25 C24 C31 112.2 . . ?
C23 C24 C31 129.9 . . ?
C24 C25 C26 122.1 . . ?
C24 C25 S6 111.1 . . ?
C26 C25 S6 126.8 . . ?
C21 C26 C25 117.9 . . ?
C21 C26 C27 112.2 . . ?
C25 C26 C27 130.0 . . ?
C28 S4 C21 91.3 . . ?
C30 S5 C23 91.3 . . ?
C32 S6 C25 91.2 . . ?
C28 C27 C26 112.6 . . ?
C28 C27 H27 123.7 . . ?
C26 C27 H27 123.7 . . ?
C27 C28 S4 112.9 . . ?
C27 C28 H28 123.6 . . ?
S4 C28 H28 123.6 . . ?
C30 C29 C22 112.7 . . ?
C30 C29 H29 123.7 . . ?
C22 C29 H29 123.7 . . ?
C29 C30 S5 112.8 . . ?
C29 C30 H30 123.6 . . ?
S5 C30 H30 123.6 . . ?
C32 C31 C24 112.7 . . ?
C32 C31 H31 123.7 . . ?
C24 C31 H31 123.7 . . ?
C31 C32 S6 112.9 . . ?
C31 C32 H32 123.6 . . ?
S6 C32 H32 123.6 . . ?
C46 C41 C42 122.1 . . ?
C46 C41 S7 111.0 . . ?
C42 C41 S7 126.8 . . ?
C43 C42 C41 117.8 . . ?
C43 C42 C49 112.2 . . ?
C41 C42 C49 130.0 . . ?
C42 C43 C44 122.1 . . ?
C42 C43 S8 111.0 . . ?
C44 C43 S8 126.8 . . ?
C45 C44 C43 117.9 . . ?
C45 C44 C51 112.1 . . ?
C43 C44 C51 130.0 . . ?
C44 C45 C46 122.1 . . ?
C44 C45 S9 111.1 . . ?
C46 C45 S9 126.8 . . ?
C41 C46 C45 117.9 . . ?
C41 C46 C47 112.2 . . ?
C45 C46 C47 130.0 . . ?
C48 S7 C41 91.3 . . ?
C50 S8 C43 91.3 . . ?
C52 S9 C45 91.3 . . ?
C48 C47 C46 112.6 . . ?
C48 C47 H47 123.7 . . ?
C46 C47 H47 123.7 . . ?
C47 C48 S7 112.9 . . ?
C47 C48 H48 123.6 . . ?
S7 C48 H48 123.6 . . ?
C50 C49 C42 112.7 . . ?
C50 C49 H49 123.7 . . ?
C42 C49 H49 123.7 . . ?
C49 C50 S8 112.8 . . ?
C49 C50 H50 123.6 . . ?
S8 C50 H50 123.6 . . ?
C52 C51 C44 112.6 . . ?
C52 C51 H51 123.7 . . ?
C44 C51 H51 123.7 . . ?
C51 C52 S9 112.9 . . ?
C51 C52 H52 123.6 . . ?
S9 C52 H52 123.6 . . ?
F1 C81 C82 117.7(9) . . ?
F1 C81 C89 118.6(8) . . ?
C82 C81 C89 123.7(9) . . ?
F2 C82 C81 119.9(9) . . ?
F2 C82 C83 118.5(8) . . ?
C81 C82 C83 121.6(9) . . ?
C84 C83 C87 122.9(9) . . ?
C84 C83 C82 122.2(9) . . ?
C87 C83 C82 114.9(8) . . ?
C83 C84 C85 124.2(10) . . ?
C83 C84 C86 124.2(10) . . ?
C85 C84 C86 111.6(9) . . ?
N1 C85 C84 174.4(12) . . ?
N2 C86 C84 174.8(12) . . ?
F3 C87 C88 118.6(9) . . ?
F3 C87 C83 118.6(8) . . ?
C88 C87 C83 122.8(9) . . ?
F4 C88 C87 118.5(9) . . ?
F4 C88 C89 117.7(8) . . ?
C87 C88 C89 123.8(9) . . ?
C90 C89 C88 123.9(9) . . ?
C90 C89 C81 122.9(9) . . ?
C88 C89 C81 113.2(8) . . ?
C89 C90 C92 123.3(10) . . ?
C89 C90 C91 123.3(10) . . ?
C92 C90 C91 113.3(9) . . ?
N3 C91 C90 172.4(12) . . ?
N4 C92 C90 171.6(12) . . ?

_refine_diff_density_max         1.348
_refine_diff_density_min         -0.848
_refine_diff_density_rms         0.101


#=======================================================================
# The following lines are used to test the character set of files sent
# by email or other means.  They are not part of the CIF data set.
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
#=======================================================================
#                              END of CIF
#=======================================================================

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
