# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_V191101b
_database_code_depnum_ccdc_archive 'CCDC 1983743'
loop_
_audit_author_name
_audit_author_address
'Tomofumi Kadoya'
;University of Hyogo
Japan
;
_audit_update_record             
;
2020-02-13 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H10 F6 P S6'
_chemical_formula_moiety         'C14 H10 F6 P S6'
_chemical_formula_weight         515.56
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
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                   36.971(15)
_cell_length_b                   4.3814(15)
_cell_length_c                   11.483(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.352(5)
_cell_angle_gamma                90.0000
_cell_volume                     1784.8(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1805
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.06
_cell_measurement_temperature    273
#------------------------------------------------------------------------------
_exptl_crystal_description       thin
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.017
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1036.00
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_T_max  0.833

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      273
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            10250
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         3.446
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1644
_reflns_number_gt                1450
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.1069
_refine_ls_wR_factor_ref         0.3406
_refine_ls_wR_factor_gt          0.3240
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1644
_refine_ls_number_parameters     124
_refine_ls_goodness_of_fit_ref   1.615
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.44
_refine_diff_density_min         -1.46
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.1023 0.0942
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.19309(3) 0.9845(3) 0.26939(11) 0.0502(7) Uani 1 1 d . . . . .
S2 S 0.14350(3) 1.4767(3) 0.51126(11) 0.0534(7) Uani 1 1 d . . . . .
S3 S 0.11153(3) 1.1036(3) 0.22895(11) 0.0580(7) Uani 1 1 d . . . . .
P13 P 0.0000 1.0000 0.0000 0.192(3) Uani 1 2 d S . P . .
F4 F -0.0003(3) 1.205(8) 0.1053(18) 0.432(17) Uani 1 1 d . . . . .
F9 F 0.0336(3) 1.172(7) 0.0021(14) 0.371(12) Uani 1 1 d . . . . .
F14 F 0.0274(5) 0.810(6) 0.0961(15) 0.358(10) Uani 1 1 d . . . . .
C1 C 0.17072(11) 1.2965(10) 0.4296(3) 0.0426(10) Uani 1 1 d . . . . .
C2 C 0.22772(13) 1.1207(10) 0.3957(4) 0.0446(11) Uani 1 1 d . . . . .
C5 C 0.09768(14) 1.3063(18) 0.4404(5) 0.0734(16) Uani 1 1 d . . . . .
H5A H 0.0986 1.0936 0.4644 0.088 Uiso 1 1 calc R U . . .
H5B H 0.0791 1.4066 0.4723 0.088 Uiso 1 1 calc R U . . .
C7 C 0.08462(16) 1.3214(17) 0.3067(6) 0.0781(17) Uani 1 1 d . . . . .
H7A H 0.0849 1.5332 0.2823 0.094 Uiso 1 1 calc R U . . .
H7B H 0.0587 1.2516 0.2803 0.094 Uiso 1 1 calc R U . . .
C10 C 0.15724(12) 1.1471(10) 0.3183(4) 0.0457(11) Uani 1 1 d . . . . .
C11 C 0.21081(10) 1.2897(9) 0.4737(3) 0.0407(10) Uani 1 1 d . . . . .
C12 C 0.23452(13) 1.4182(10) 0.5804(4) 0.0464(11) Uani 1 1 d . . . . .
H12 H 0.2245 1.5275 0.6334 0.056 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C10 1.731(5) . ?
S1 C2 1.747(5) . ?
S2 C1 1.745(4) . ?
S2 C5 1.820(6) . ?
S3 C10 1.723(4) . ?
S3 C7 1.788(7) . ?
P13 F9 1.447(17) 5_575 ?
P13 F9 1.447(17) . ?
P13 F14 1.520(15) 5_575 ?
P13 F14 1.520(15) . ?
P13 F4 1.508(15) 5_575 ?
P13 F4 1.508(15) . ?
F4 F14 2.03(3) . ?
F9 F14 1.97(3) . ?
C1 C10 1.398(6) . ?
C1 C11 1.425(6) . ?
C2 C12 1.356(6) 7_576 ?
C2 C11 1.434(6) . ?
C5 C7 1.476(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C11 C12 1.408(6) . ?
C12 C2 1.356(6) 7_576 ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 C2 92.2(2) . . ?
C1 S2 C5 100.3(2) . . ?
C10 S3 C7 103.5(2) . . ?
F9 P13 F9 180.0 5_575 . ?
F9 P13 F14 83.1(10) 5_575 5_575 ?
F9 P13 F14 96.9(10) . 5_575 ?
F9 P13 F14 96.9(10) 5_575 . ?
F9 P13 F14 83.1(10) . . ?
F14 P13 F14 180.0 5_575 . ?
F9 P13 F4 83.0(13) 5_575 5_575 ?
F9 P13 F4 97.0(13) . 5_575 ?
F14 P13 F4 84.2(14) 5_575 5_575 ?
F14 P13 F4 95.8(14) . 5_575 ?
F9 P13 F4 97.0(13) 5_575 . ?
F9 P13 F4 83.0(13) . . ?
F14 P13 F4 95.8(14) 5_575 . ?
F14 P13 F4 84.2(14) . . ?
F4 P13 F4 180.0 5_575 . ?
P13 F4 F14 48.2(8) . . ?
P13 F9 F14 50.0(8) . . ?
P13 F14 F4 47.7(8) . . ?
P13 F14 F9 46.9(6) . . ?
F4 F14 F9 58.7(12) . . ?
C10 C1 C11 112.5(4) . . ?
C10 C1 S2 126.3(3) . . ?
C11 C1 S2 121.2(3) . . ?
C12 C2 C11 122.9(4) 7_576 . ?
C12 C2 S1 126.7(3) 7_576 . ?
C11 C2 S1 110.4(3) . . ?
C7 C5 S2 115.9(4) . . ?
C7 C5 H5A 108.3 . . ?
S2 C5 H5A 108.3 . . ?
C7 C5 H5B 108.3 . . ?
S2 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C5 C7 S3 115.5(5) . . ?
C5 C7 H7A 108.4 . . ?
S3 C7 H7A 108.4 . . ?
C5 C7 H7B 108.4 . . ?
S3 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C1 C10 S3 129.3(3) . . ?
C1 C10 S1 112.4(3) . . ?
S3 C10 S1 118.3(3) . . ?
C12 C11 C1 129.1(4) . . ?
C12 C11 C2 118.4(3) . . ?
C1 C11 C2 112.4(3) . . ?
C2 C12 C11 118.6(4) 7_576 . ?
C2 C12 H12 120.7 7_576 . ?
C11 C12 H12 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
F9 P13 F4 F14 96.3(11) 5_575 . . . ?
F9 P13 F4 F14 -83.7(11) . . . . ?
F14 P13 F4 F14 180.003(7) 5_575 . . . ?
F14 P13 F9 F14 180.002(0) 5_575 . . . ?
F4 P13 F9 F14 -95.1(14) 5_575 . . . ?
F4 P13 F9 F14 84.9(14) . . . . ?
F9 P13 F14 F4 -96.4(15) 5_575 . . . ?
F9 P13 F14 F4 83.6(15) . . . . ?
F4 P13 F14 F4 180.003(7) 5_575 . . . ?
F9 P13 F14 F9 179.999(2) 5_575 . . . ?
F4 P13 F14 F9 96.4(15) 5_575 . . . ?
F4 P13 F14 F9 -83.6(15) . . . . ?
C5 S2 C1 C10 17.9(5) . . . . ?
C5 S2 C1 C11 -162.2(4) . . . . ?
C10 S1 C2 C12 -179.0(4) . . . 7_576 ?
C10 S1 C2 C11 0.1(3) . . . . ?
C1 S2 C5 C7 -51.8(5) . . . . ?
S2 C5 C7 S3 66.4(6) . . . . ?
C10 S3 C7 C5 -37.7(5) . . . . ?
C11 C1 C10 S3 -178.4(3) . . . . ?
S2 C1 C10 S3 1.6(6) . . . . ?
C11 C1 C10 S1 2.4(5) . . . . ?
S2 C1 C10 S1 -177.7(2) . . . . ?
C7 S3 C10 C1 4.2(5) . . . . ?
C7 S3 C10 S1 -176.6(3) . . . . ?
C2 S1 C10 C1 -1.4(3) . . . . ?
C2 S1 C10 S3 179.2(3) . . . . ?
C10 C1 C11 C12 178.9(4) . . . . ?
S2 C1 C11 C12 -1.1(6) . . . . ?
C10 C1 C11 C2 -2.4(5) . . . . ?
S2 C1 C11 C2 177.7(3) . . . . ?
C12 C2 C11 C12 -0.7(7) 7_576 . . . ?
S1 C2 C11 C12 -179.8(3) . . . . ?
C12 C2 C11 C1 -179.6(4) 7_576 . . . ?
S1 C2 C11 C1 1.3(4) . . . . ?
C1 C11 C12 C2 179.3(4) . . . 7_576 ?
C2 C11 C12 C2 0.6(6) . . . 7_576 ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014-3


