# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_f2p
_database_code_depnum_ccdc_archive 'CCDC 1856883'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2017-05-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 F2 S2'
_chemical_formula_sum            'C14 H8 F2 S2'
_chemical_formula_weight         278.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   7.4893(9)
_cell_length_b                   3.8493(4)
_cell_length_c                   19.835(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.273(4)
_cell_angle_gamma                90
_cell_volume                     570.23(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5897
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.512
_cell_measurement_theta_min      2.728
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.7314
_exptl_absorpt_correction_T_min  0.4838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1756 before and 0.0872 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1821 before and 0.0930 after correction.
 The Ratio of minimum to maximum transmission is 0.54.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 13183 reflections, Rint = 0.0842
 (10786 with I > 3sig(I), Rint = 0.0823)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.423
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            976
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        24.977
_diffrn_reflns_theta_max         24.977
_diffrn_reflns_theta_min         2.727
_diffrn_ambient_temperature      110.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                854
_reflns_number_total             976
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.342
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         976
_refine_ls_number_restraints     220
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0787
_refine_ls_restrained_S_all      1.224
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+2.8130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.1703
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{C4, C4A}
3. Uiso/Uaniso restraints and constraints
C4 \\sim C5 \\sim C6 \\sim C7 \\sim S8 \\sim C4A \\sim C5A \\sim C6A \\sim C7A
\\sim S8A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C4) = Uanis(C4A)
Uanis(S8) = Uanis(C5A)
Uanis(C5) = Uanis(S8A)
4. Rigid body (RIGU) restrains
 C4, C5, C6, C7, S8, C4A, C5A, C6A, C7A, S8A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Same fragment restrains
{C4, C5, C6, C7, S8} sigma for 1-2: 0.02, 1-3: 0.04
as
{C4A, C5A, C6A, C7A, S8A}
6. Others
 Sof(C4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(S8A)=1-
 FVAR(1)
 Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(S8)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C7(H7), C5A(H5A), C6A(H6A), C7A(H7A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.6667(4) 0.5863(9) 0.62464(12) 0.0294(8) Uani 1 1 d . . . . .
C1 C 0.6756(6) 0.4008(13) 0.5132(2) 0.0173(10) Uani 1 1 d . . . . .
H1 H 0.7970 0.3368 0.5237 0.021 Uiso 1 1 calc R . . . .
C2 C 0.5791(6) 0.5457(13) 0.5623(2) 0.0159(10) Uani 1 1 d . . . . .
C3 C 0.4031(6) 0.6534(12) 0.5523(2) 0.0143(10) Uani 1 1 d . . . . .
C4 C 0.2995(5) 0.8038(12) 0.6053(2) 0.0145(9) Uani 0.597(6) 1 d D U P A 1
C5 C 0.358(2) 0.902(6) 0.6699(8) 0.0196(11) Uani 0.597(6) 1 d D U P A 1
H5 H 0.4770 0.8828 0.6899 0.024 Uiso 0.597(6) 1 calc R . P A 1
C6 C 0.1910(17) 1.052(7) 0.7045(9) 0.018(2) Uani 0.597(6) 1 d D U P A 1
H6 H 0.1926 1.1430 0.7491 0.022 Uiso 0.597(6) 1 calc R . P A 1
C7 C 0.046(2) 1.029(6) 0.6605(7) 0.019(2) Uani 0.597(6) 1 d D U P A 1
H7 H -0.0682 1.1026 0.6722 0.023 Uiso 0.597(6) 1 calc R . P A 1
S8 S 0.0745(3) 0.8767(11) 0.59023(15) 0.0183(7) Uani 0.597(6) 1 d D U P A 1
C4A C 0.2995(5) 0.8038(12) 0.6053(2) 0.0145(9) Uani 0.403(6) 1 d D U P A 2
C5A C 0.117(2) 0.873(8) 0.5992(11) 0.0183(7) Uani 0.403(6) 1 d D U P A 2
H5A H 0.0366 0.8315 0.5607 0.022 Uiso 0.403(6) 1 calc R . P A 2
C6A C 0.069(3) 1.041(9) 0.6712(10) 0.017(2) Uani 0.403(6) 1 d D U P A 2
H6A H -0.0459 1.1146 0.6831 0.020 Uiso 0.403(6) 1 calc R . P A 2
C7A C 0.222(3) 1.053(10) 0.7100(14) 0.018(2) Uani 0.403(6) 1 d D U P A 2
H7A H 0.2250 1.1497 0.7542 0.022 Uiso 0.403(6) 1 calc R . P A 2
S8A S 0.3883(8) 0.915(2) 0.6833(2) 0.0196(11) Uani 0.403(6) 1 d D 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 1.366(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.373(6) . ?
C1 C3 1.402(6) 3_666 ?
C2 C3 1.381(6) . ?
C3 C1 1.402(6) 3_666 ?
C3 C4 1.470(6) . ?
C3 C4A 1.470(6) . ?
C4 C5 1.376(14) . ?
C4 S8 1.712(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.58(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.342(11) . ?
C7 H7 0.9500 . ?
C7 S8 1.540(14) . ?
C4A C5A 1.388(17) . ?
C4A S8A 1.692(5) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.63(2) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.336(14) . ?
C7A H7A 0.9500 . ?
C7A S8A 1.488(19) . ?

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 H1 119.7 . . ?
C2 C1 C3 120.7(4) . 3_666 ?
C3 C1 H1 119.7 3_666 . ?
F1 C2 C1 116.5(4) . . ?
F1 C2 C3 118.9(4) . . ?
C1 C2 C3 124.6(4) . . ?
C1 C3 C4 120.9(4) 3_666 . ?
C1 C3 C4A 120.9(4) 3_666 . ?
C2 C3 C1 114.7(4) . 3_666 ?
C2 C3 C4 124.4(4) . . ?
C2 C3 C4A 124.4(4) . . ?
C3 C4 S8 120.3(3) . . ?
C5 C4 C3 128.6(9) . . ?
C5 C4 S8 111.0(8) . . ?
C4 C5 H5 126.4 . . ?
C4 C5 C6 107.2(11) . . ?
C6 C5 H5 126.4 . . ?
C5 C6 H6 125.7 . . ?
C7 C6 C5 108.6(15) . . ?
C7 C6 H6 125.7 . . ?
C6 C7 H7 121.4 . . ?
C6 C7 S8 117.2(15) . . ?
S8 C7 H7 121.4 . . ?
C7 S8 C4 95.9(6) . . ?
C3 C4A S8A 124.1(4) . . ?
C5A C4A C3 125.6(9) . . ?
C5A C4A S8A 110.3(9) . . ?
C4A C5A H5A 126.8 . . ?
C4A C5A C6A 106.4(13) . . ?
C6A C5A H5A 126.8 . . ?
C5A C6A H6A 126.9 . . ?
C7A C6A C5A 106(2) . . ?
C7A C6A H6A 126.9 . . ?
C6A C7A H7A 120.4 . . ?
C6A C7A S8A 119(2) . . ?
S8A C7A H7A 120.4 . . ?
C7A S8A C4A 97.7(10) . . ?

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
F1 C2 C3 C1 -179.7(4) . . . 3_666 ?
F1 C2 C3 C4 -1.6(7) . . . . ?
F1 C2 C3 C4A -1.6(7) . . . . ?
C1 C2 C3 C1 1.0(8) . . . 3_666 ?
C1 C2 C3 C4 179.1(5) . . . . ?
C1 C2 C3 C4A 179.1(5) . . . . ?
C1 C3 C4 C5 -173.9(13) 3_666 . . . ?
C1 C3 C4 S8 6.4(7) 3_666 . . . ?
C1 C3 C4A C5A 6.6(17) 3_666 . . . ?
C1 C3 C4A S8A -173.7(5) 3_666 . . . ?
C2 C3 C4 C5 8.2(15) . . . . ?
C2 C3 C4 S8 -171.6(4) . . . . ?
C2 C3 C4A C5A -171.3(16) . . . . ?
C2 C3 C4A S8A 8.3(8) . . . . ?
C3 C1 C2 F1 179.6(4) 3_666 . . . ?
C3 C1 C2 C3 -1.1(8) 3_666 . . . ?
C3 C4 C5 C6 179.2(11) . . . . ?
C3 C4 S8 C7 -179.7(10) . . . . ?
C3 C4A C5A C6A -179.4(14) . . . . ?
C3 C4A S8A C7A 178.6(16) . . . . ?
C4 C5 C6 C7 1(2) . . . . ?
C5 C4 S8 C7 0.5(13) . . . . ?
C5 C6 C7 S8 -1(2) . . . . ?
C6 C7 S8 C4 0.3(18) . . . . ?
S8 C4 C5 C6 -1.0(17) . . . . ?
C4A C5A C6A C7A 0(3) . . . . ?
C5A C4A S8A C7A -2(2) . . . . ?
C5A C6A C7A S8A -2(4) . . . . ?
C6A C7A S8A C4A 2(3) . . . . ?
S8A C4A C5A C6A 1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1856885'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
# end Validation Reply Form
_audit_creation_date             2017-08-18
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1.4(C8.54 H4.27 F0.71 N1.42 S1.42)'
_chemical_formula_sum            'C12 H6 F N2 S2'
_chemical_formula_weight         261.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.9315(6)
_cell_length_b                   4.9497(5)
_cell_length_c                   18.794(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.890(4)
_cell_angle_gamma                90
_cell_volume                     548.85(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3497
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.701
_cell_measurement_theta_min      3.272
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1439 before and 0.0601 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1654 before and 0.0805 after correction.
 The Ratio of minimum to maximum transmission is 0.76.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 10163 reflections, Rint = 0.0586
 (7686 with I > 3sig(I), Rint = 0.0567)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.094
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1289
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        22.487
_diffrn_reflns_theta_max         22.487
_diffrn_reflns_theta_min         2.179
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1156
_reflns_number_total             1289
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1289
_refine_ls_number_restraints     468
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0818
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0262P)²+1.6061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1590
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.860(3)
 0.140(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C3-C1_$1 \\sim C2_$1-C1_$1 \\sim C3_$1-C2_$1 \\sim C3_$1-C1 \\sim C2-C1 \\sim
C3-C2 \\sim C3A-C1A_$1
 \\sim C2A_$1-C1A_$1 \\sim C3A_$1-C2A_$1 \\sim C3A_$1-C1A \\sim C2A-C1A \\sim
C3A-C2A
 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim F3 \\sim N2 \\sim S1
\\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim F3A \\sim N2A
\\sim S1A: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N2) = Uanis(N2A)
Uanis(S1A) = Uanis(S1)
Uanis(F3) = Uanis(F3A)
Uanis(C2) = Uanis(C2A)
Uanis(C1) = Uanis(C1A)
Uanis(C3) = Uanis(C3A)
5. Rigid body (RIGU) restrains
 C1, C2, C3, C4, C5, C6, F3, N2, S1, C1A, C2A, C3A, C4A, C5A, C6A, F3A, N2A, S1A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
6. Same fragment restrains
{C1, C2, C3, C4, C5, C6, F3, N2, S1} sigma for 1-2: 0.005, 1-3: 0.04
as
{C1A, C2A, C3A, C4A, C5A, C6A, F3A, N2A, S1A}
7. Others
 Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(C3A)=Sof(C4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=
 Sof(H6A)=Sof(N2A)=Sof(S1A)=1-FVAR(1)
 Sof(F3A)=0.5*(1-FVAR(2))
 Sof(F3)=0.5*FVAR(2)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=
 Sof(N2)=Sof(S1)=FVAR(1)
8.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C1A(H1A), C5A(H5A), C6A(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.698(2) 1.137(4) 0.5058(8) 0.0378(17) Uani 0.712(5) 1 d D U P A 1
H1 H 0.838160 1.231150 0.511939 0.045 Uiso 0.712(5) 1 calc R . P A 1
C2 C 0.6565(19) 0.942(4) 0.5563(8) 0.0364(14) Uani 0.712(5) 1 d D U P A 1
C3 C 0.454(2) 0.797(4) 0.5534(8) 0.0347(13) Uani 0.712(5) 1 d D U P A 1
C4 C 0.4052(18) 0.593(2) 0.6061(6) 0.0358(15) Uani 0.712(5) 1 d D U P A 1
C5 C 0.4076(15) 0.281(2) 0.7048(5) 0.0388(18) Uani 0.712(5) 1 d D U P A 1
H5 H 0.432230 0.169950 0.746204 0.047 Uiso 0.712(5) 1 calc R . P A 1
C6 C 0.2184(16) 0.2846(19) 0.6599(5) 0.0402(18) Uani 0.712(5) 1 d D U P A 1
H6 H 0.098664 0.162685 0.666481 0.048 Uiso 0.712(5) 1 calc R . P A 1
F3 F 0.802(2) 0.907(3) 0.6138(6) 0.038(3) Uani 0.356(2) 1 d D U P A 1
N2 N 0.196(2) 0.471(3) 0.6023(7) 0.0393(16) Uani 0.712(5) 1 d D U P A 1
S1 S 0.5967(5) 0.5020(6) 0.67718(15) 0.0426(9) Uani 0.712(5) 1 d D U P A 1
C1A C 0.720(5) 1.153(10) 0.499(2) 0.0378(17) Uani 0.288(5) 1 d D U P A 2
H1A H 0.855917 1.252566 0.496403 0.045 Uiso 0.288(5) 1 calc R . P A 2
C2A C 0.683(4) 0.961(9) 0.550(2) 0.0364(14) Uani 0.288(5) 1 d D U P A 2
C3A C 0.475(5) 0.827(9) 0.549(2) 0.0347(13) Uani 0.288(5) 1 d D U P A 2
C4A C 0.462(4) 0.634(5) 0.6076(13) 0.0379(18) Uani 0.288(5) 1 d D U P A 2
C5A C 0.328(4) 0.281(5) 0.6866(10) 0.041(2) Uani 0.288(5) 1 d D U P A 2
H5A H 0.252836 0.148781 0.712412 0.049 Uiso 0.288(5) 1 calc R . P A 2
C6A C 0.535(3) 0.382(4) 0.7039(12) 0.041(2) Uani 0.288(5) 1 d D U P A 2
H6A H 0.625559 0.309159 0.743835 0.049 Uiso 0.288(5) 1 calc R . P A 2
F3A F 0.834(5) 0.852(8) 0.5986(16) 0.038(3) Uani 0.144(2) 1 d D U P A 2
N2A N 0.623(4) 0.596(5) 0.6649(12) 0.0393(16) Uani 0.288(5) 1 d D U P A 2
S1A S 0.2272(17) 0.434(2) 0.6096(6) 0.0426(9) Uani 0.288(5) 1 d D 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
C1 H1 0.9500 . ?
C1 C2 1.394(5) . ?
C1 C3 1.398(5) 3_676 ?
C2 C3 1.394(5) . ?
C2 F3 1.325(10) . ?
C3 C4 1.463(9) . ?
C4 N2 1.377(15) . ?
C4 S1 1.722(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.334(13) . ?
C5 S1 1.687(9) . ?
C6 H6 0.9500 . ?
C6 N2 1.417(15) . ?
C1A H1A 0.9500 . ?
C1A C2A 1.394(5) . ?
C1A C3A 1.397(5) 3_676 ?
C2A C3A 1.396(5) . ?
C2A F3A 1.324(11) . ?
C3A C4A 1.461(11) . ?
C4A N2A 1.377(16) . ?
C4A S1A 1.714(12) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.334(15) . ?
C5A S1A 1.688(10) . ?
C6A H6A 0.9500 . ?
C6A N2A 1.417(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
C2 C1 H1 118.0 . . ?
C2 C1 C3 124.1(10) . 3_676 ?
C3 C1 H1 118.0 3_676 . ?
C1 C2 C3 122.8(9) . . ?
F3 C2 C1 120.2(11) . . ?
F3 C2 C3 116.7(9) . . ?
C1 C3 C4 122.8(9) 3_676 . ?
C2 C3 C1 113.1(7) . 3_676 ?
C2 C3 C4 124.0(8) . . ?
C3 C4 S1 123.0(7) . . ?
N2 C4 C3 120.6(9) . . ?
N2 C4 S1 116.4(7) . . ?
C6 C5 H5 125.1 . . ?
C6 C5 S1 109.7(7) . . ?
S1 C5 H5 125.1 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 N2 120.1(9) . . ?
N2 C6 H6 120.0 . . ?
C4 N2 C6 103.4(9) . . ?
C5 S1 C4 90.2(4) . . ?
C2A C1A H1A 125.7 . . ?
C2A C1A C3A 109(2) . 3_676 ?
C3A C1A H1A 125.7 3_676 . ?
C1A C2A C3A 121(2) . . ?
F3A C2A C1A 128(2) . . ?
F3A C2A C3A 111(2) . . ?
C1A C3A C4A 115(2) 3_676 . ?
C2A C3A C4A 114.4(17) . . ?
C3A C4A S1A 120.0(15) . . ?
N2A C4A C3A 126.2(16) . . ?
N2A C4A S1A 113.8(13) . . ?
C6A C5A H5A 127.0 . . ?
C6A C5A S1A 105.9(14) . . ?
S1A C5A H5A 127.0 . . ?
C5A C6A H6A 118.8 . . ?
C5A C6A N2A 122.4(18) . . ?
N2A C6A H6A 118.8 . . ?
C4A N2A C6A 104.0(15) . . ?
C5A S1A C4A 93.5(11) . . ?

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
C1 C2 C3 C1 1(3) . . . 3_676 ?
C1 C2 C3 C4 -179.2(19) . . . . ?
C1 C3 C4 N2 -5(3) 3_676 . . . ?
C1 C3 C4 S1 177.4(19) 3_676 . . . ?
C2 C3 C4 N2 175.8(18) . . . . ?
C2 C3 C4 S1 -2(3) . . . . ?
C3 C1 C2 C3 -2(4) 3_676 . . . ?
C3 C1 C2 F3 -175(2) 3_676 . . . ?
C3 C4 N2 C6 178.1(14) . . . . ?
C3 C4 S1 C5 179.9(14) . . . . ?
C5 C6 N2 C4 5.1(15) . . . . ?
C6 C5 S1 C4 1.0(8) . . . . ?
F3 C2 C3 C1 175(2) . . . 3_676 ?
F3 C2 C3 C4 -6(3) . . . . ?
N2 C4 S1 C5 2.0(11) . . . . ?
S1 C4 N2 C6 -4.0(14) . . . . ?
S1 C5 C6 N2 -3.9(13) . . . . ?
C1A C2A C3A C1A 1(10) . . . 3_676 ?
C1A C2A C3A C4A -179(5) . . . . ?
C1A C3A C4A N2A -173(5) 3_676 . . . ?
C1A C3A C4A S1A 5(6) 3_676 . . . ?
C2A C3A C4A N2A 7(6) . . . . ?
C2A C3A C4A S1A -175(3) . . . . ?
C3A C1A C2A C3A -1(8) 3_676 . . . ?
C3A C1A C2A F3A 169(6) 3_676 . . . ?
C3A C4A N2A C6A -178(4) . . . . ?
C3A C4A S1A C5A -179(3) . . . . ?
C5A C6A N2A C4A -6(4) . . . . ?
C6A C5A S1A C4A -2(2) . . . . ?
F3A C2A C3A C1A -170(7) . . . 3_676 ?
F3A C2A C3A C4A 10(6) . . . . ?
N2A C4A S1A C5A -1(3) . . . . ?
S1A C4A N2A C6A 4(3) . . . . ?
S1A C5A C6A N2A 6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.860(3)
2 0.140(3)

_vrf_PLAT088_4                   
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.32 Note  
RESPONSE: The structure has a whole molecule disorder resulting in
doubled the atoms being refined, and consequently the increase in
parameters. A significant number of restraints, instead of constraints, 
were used to keep the bond distances, angles, and thermal ellipsoids
meaningful.
;
# start Validation Reply Form
_vrf_THETM01_4                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal quality was poor. Due to significant disorder, 
a whole molecule disorder, along with half occupancy of the F atoms
no signigicant reflections were found above 45 degrees 2-theta. The
final refinements were restricted to that angle.
;
####################################################################### 
# 
# 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_f2r
_database_code_depnum_ccdc_archive 'CCDC 1856886'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_f2r                 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.935 Note  
RESPONSE: Data collected with Copper radiation for puesdo-orthorhombic cell
;
# end Validation Reply Form
_audit_creation_date             2017-06-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 F2 N2 S2'
_chemical_formula_sum            'C12 H6 F2 N2 S2'
_chemical_formula_weight         280.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.7427(3)
_cell_length_b                   5.5541(3)
_cell_length_c                   17.1753(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.509(2)
_cell_angle_gamma                90
_cell_volume                     547.79(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2797
_cell_measurement_temperature    100
_cell_measurement_theta_max      77.34
_cell_measurement_theta_min      5.15
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.551
_exptl_absorpt_coefficient_mu    4.514
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0974 before and 0.0450 after correction. The Ratio of minimum to maximum transmission is 0.7225. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3760
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.795
_diffrn_reflns_theta_min         5.150
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker CMOS area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Micro-Source CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                964
_reflns_number_total             1047
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       APEX3
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1047
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+0.3489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0850
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.40356(8) 0.52263(8) 0.31778(2) 0.02101(18) Uani 1 1 d . . . . .
F1 F 0.1885(2) 0.9110(2) 0.38417(6) 0.0244(3) Uani 1 1 d . . . . .
N1 N 0.7715(3) 0.4682(3) 0.40210(9) 0.0200(4) Uani 1 1 d . . . . .
C1 C 0.3023(3) 1.1446(3) 0.49160(10) 0.0187(4) Uani 1 1 d . . . . .
H1 H 0.166638 1.240449 0.484751 0.022 Uiso 1 1 calc R . . . .
C2 C 0.3454(4) 0.9551(3) 0.44247(10) 0.0190(4) Uani 1 1 d . . . . .
C3 C 0.5392(3) 0.8049(3) 0.44797(10) 0.0176(4) Uani 1 1 d . . . . .
C4 C 0.5852(3) 0.6045(3) 0.39493(10) 0.0180(4) Uani 1 1 d . . . . .
C5 C 0.7736(4) 0.2950(3) 0.34539(10) 0.0224(4) Uani 1 1 d . . . . .
H5 H 0.895694 0.180136 0.341909 0.027 Uiso 1 1 calc R . . . .
C6 C 0.5916(4) 0.2965(3) 0.29442(10) 0.0217(4) Uani 1 1 d . . . . .
H6 H 0.571834 0.187973 0.252113 0.026 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 C4 1.7396(18) . ?
S1 C6 1.707(2) . ?
F1 C2 1.363(2) . ?
N1 C4 1.315(2) . ?
N1 C5 1.369(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.373(3) . ?
C1 C3 1.403(3) 3_676 ?
C2 C3 1.393(3) . ?
C3 C4 1.464(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.358(3) . ?
C6 H6 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
C6 S1 C4 89.71(9) . . ?
C4 N1 C5 110.48(16) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C3 119.25(18) . 3_676 ?
C3 C1 H1 120.4 3_676 . ?
F1 C2 C1 117.87(17) . . ?
F1 C2 C3 117.70(16) . . ?
C1 C2 C3 124.43(18) . . ?
C1 C3 C4 119.51(17) 3_676 . ?
C2 C3 C1 116.33(16) . 3_676 ?
C2 C3 C4 124.16(17) . . ?
N1 C4 S1 113.76(14) . . ?
N1 C4 C3 122.04(16) . . ?
C3 C4 S1 124.20(14) . . ?
N1 C5 H5 121.9 . . ?
C6 C5 N1 116.28(18) . . ?
C6 C5 H5 121.9 . . ?
S1 C6 H6 125.1 . . ?
C5 C6 S1 109.76(14) . . ?
C5 C6 H6 125.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_f4p
_database_code_depnum_ccdc_archive 'CCDC 1856884'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2017-06-14
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H6 F4 S2'
_chemical_formula_sum            'C14 H6 F4 S2'
_chemical_formula_weight         314.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.2999(3)
_cell_length_b                   5.0655(3)
_cell_length_c                   18.6515(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.341(2)
_cell_angle_gamma                90
_cell_volume                     595.20(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4287
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.096
_cell_measurement_theta_min      4.742
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.411
_exptl_absorpt_coefficient_mu    4.434
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1131 before and 0.0572 after correction.
 The Ratio of minimum to maximum transmission is 0.52.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1755 before and 0.1014 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 11761 reflections, Rint = 0.0724
 (9057 with I > 3sig(I), Rint = 0.0710)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1110
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.090
_diffrn_reflns_theta_min         4.742
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1019
_reflns_number_total             1110
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+1.3912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1070
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.38499(11) 1.00713(15) 0.33096(4) 0.0210(2) Uani 1 1 d . . . . .
F1 F 0.1976(2) 0.5928(3) 0.39976(8) 0.0201(4) Uani 1 1 d . . . . .
F2 F 0.1305(2) 0.2316(4) 0.49483(9) 0.0227(4) Uani 1 1 d . . . . .
C1 C 0.5479(5) 1.2385(6) 0.29432(15) 0.0229(7) Uani 1 1 d . . . . .
H1 H 0.5074 1.3529 0.2563 0.028 Uiso 1 1 calc R . . . .
C2 C 0.7415(5) 1.2400(6) 0.32587(15) 0.0217(6) Uani 1 1 d . . . . .
H2 H 0.8524 1.3559 0.3120 0.026 Uiso 1 1 calc R . . . .
C3 C 0.7632(4) 1.0528(5) 0.38142(14) 0.0146(5) Uani 1 1 d . . . . .
H3 H 0.8896 1.0288 0.4087 0.018 Uiso 1 1 calc R . . . .
C4 C 0.5780(4) 0.9070(6) 0.39186(14) 0.0160(6) Uani 1 1 d . . . . .
C5 C 0.5380(4) 0.7028(6) 0.44588(14) 0.0153(6) Uani 1 1 d . . . . .
C6 C 0.3528(4) 0.5534(6) 0.44899(14) 0.0157(6) Uani 1 1 d . . . . .
C7 C 0.3165(4) 0.3618(6) 0.50015(14) 0.0157(6) 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 1.704(3) . ?
S1 C4 1.735(3) . ?
F1 C6 1.352(3) . ?
F2 C7 1.348(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.351(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.410(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(4) . ?
C4 C5 1.467(4) . ?
C5 C6 1.392(4) . ?
C5 C7 1.396(4) 3_666 ?
C6 C7 1.381(4) . ?
C7 C5 1.396(4) 3_666 ?

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 92.42(14) . . ?
S1 C1 H1 124.0 . . ?
C2 C1 S1 111.9(2) . . ?
C2 C1 H1 124.0 . . ?
C1 C2 H2 123.2 . . ?
C1 C2 C3 113.6(3) . . ?
C3 C2 H2 123.2 . . ?
C2 C3 H3 123.8 . . ?
C4 C3 C2 112.4(2) . . ?
C4 C3 H3 123.8 . . ?
C3 C4 S1 109.7(2) . . ?
C3 C4 C5 128.0(2) . . ?
C5 C4 S1 122.2(2) . . ?
C6 C5 C4 124.0(3) . . ?
C6 C5 C7 112.9(3) . 3_666 ?
C7 C5 C4 123.1(2) 3_666 . ?
F1 C6 C5 119.6(3) . . ?
F1 C6 C7 116.8(2) . . ?
C7 C6 C5 123.6(3) . . ?
F2 C7 C5 120.3(3) . 3_666 ?
F2 C7 C6 116.2(2) . . ?
C6 C7 C5 123.5(2) . 3_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 -0.3(3) . . . . ?
S1 C4 C5 C6 6.7(4) . . . . ?
S1 C4 C5 C7 -173.3(2) . . . 3_666 ?
F1 C6 C7 F2 0.9(4) . . . . ?
F1 C6 C7 C5 179.6(2) . . . 3_666 ?
C1 S1 C4 C3 -0.8(2) . . . . ?
C1 S1 C4 C5 177.8(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 S1 0.7(3) . . . . ?
C2 C3 C4 C5 -177.7(3) . . . . ?
C3 C4 C5 C6 -175.1(3) . . . . ?
C3 C4 C5 C7 4.9(4) . . . 3_666 ?
C4 S1 C1 C2 0.6(2) . . . . ?
C4 C5 C6 F1 0.4(4) . . . . ?
C4 C5 C6 C7 -179.9(3) . . . . ?
C5 C6 C7 F2 -178.8(2) . . . . ?
C5 C6 C7 C5 -0.2(5) . . . 3_666 ?
C7 C5 C6 F1 -179.6(2) 3_666 . . . ?
C7 C5 C6 C7 0.1(4) 3_666 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xj1f
_database_code_depnum_ccdc_archive 'CCDC 1856896'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2016-12-20
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H46 F N2 S2 Si2'
_chemical_formula_sum            'C30 H46 F N2 S2 Si2'
_chemical_formula_weight         573.99
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3302(4)
_cell_length_b                   12.3529(5)
_cell_length_c                   14.5826(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.1850(10)
_cell_angle_gamma                90
_cell_volume                     1614.11(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9776
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.062
_cell_measurement_theta_min      4.774
_shelx_estimated_absorpt_T_max   0.786
_shelx_estimated_absorpt_T_min   0.456
_exptl_absorpt_coefficient_mu    2.410
_exptl_absorpt_correction_T_max  0.6963
_exptl_absorpt_correction_T_min  0.5409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1052 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.7768.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             618
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.105
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18663
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.091
_diffrn_reflns_theta_min         4.773
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2819
_reflns_number_total             3060
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.6562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0757
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F1(0.5)
3.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C13(H13)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.63701(3) 0.55428(3) 0.26896(2) 0.01664(10) Uani 1 1 d . . . . .
Si1 Si 0.29222(4) 0.58391(3) 0.16144(2) 0.01296(10) Uani 1 1 d . . . . .
F1 F 1.05095(18) 0.40799(15) 0.67081(12) 0.0238(4) Uani 0.5 1 d . . P . .
N1 N 0.44286(13) 0.58079(9) 0.36087(8) 0.0165(2) Uani 1 1 d . . . . .
C1 C 0.45494(15) 0.57649(10) 0.27302(10) 0.0143(3) Uani 1 1 d . . . . .
C2 C 0.57859(15) 0.56629(11) 0.42651(9) 0.0156(3) Uani 1 1 d . . . . .
H2 H 0.5890 0.5680 0.4932 0.019 Uiso 1 1 calc R . . . .
C3 C 0.69820(15) 0.54923(10) 0.39182(9) 0.0139(3) Uani 1 1 d . . . . .
C4 C 0.85203(15) 0.52519(10) 0.44672(9) 0.0146(3) Uani 1 1 d . . . . .
C5 C 0.88063(15) 0.47622(11) 0.53670(10) 0.0165(3) Uani 1 1 d . . . . .
H5 H 0.8004 0.4594 0.5625 0.020 Uiso 1 1 calc R . . . .
C6 C 1.02560(16) 0.45247(11) 0.58779(10) 0.0172(3) Uani 1 1 d . . . . .
C7 C 0.37105(17) 0.63184(12) 0.06241(10) 0.0227(3) Uani 1 1 d . . . . .
H7 H 0.4477 0.5770 0.0580 0.027 Uiso 1 1 calc R . . . .
C8 C 0.45198(19) 0.74099(13) 0.07878(12) 0.0293(4) Uani 1 1 d . . . . .
H8A H 0.3789 0.7994 0.0730 0.044 Uiso 1 1 calc GR . . . .
H8B H 0.5067 0.7511 0.0310 0.044 Uiso 1 1 calc GR . . . .
H8C H 0.5222 0.7424 0.1428 0.044 Uiso 1 1 calc GR . . . .
C9 C 0.2542(3) 0.6316(2) -0.03507(13) 0.0570(7) Uani 1 1 d . . . . .
H9A H 0.2099 0.5593 -0.0480 0.085 Uiso 1 1 calc GR . . . .
H9B H 0.3020 0.6509 -0.0848 0.085 Uiso 1 1 calc GR . . . .
H9C H 0.1760 0.6844 -0.0348 0.085 Uiso 1 1 calc GR . . . .
C10 C 0.21612(16) 0.44218(11) 0.13383(10) 0.0186(3) Uani 1 1 d . . . . .
H10 H 0.1259 0.4474 0.0776 0.022 Uiso 1 1 calc R . . . .
C11 C 0.32610(19) 0.36531(13) 0.10595(13) 0.0303(4) Uani 1 1 d . . . . .
H11A H 0.3526 0.3945 0.0503 0.045 Uiso 1 1 calc GR . . . .
H11B H 0.2796 0.2940 0.0902 0.045 Uiso 1 1 calc GR . . . .
H11C H 0.4164 0.3583 0.1595 0.045 Uiso 1 1 calc GR . . . .
C12 C 0.1651(2) 0.39421(13) 0.21656(13) 0.0309(4) Uani 1 1 d . . . . .
H12A H 0.2505 0.3891 0.2735 0.046 Uiso 1 1 calc GR . . . .
H12B H 0.1234 0.3219 0.1989 0.046 Uiso 1 1 calc GR . . . .
H12C H 0.0886 0.4410 0.2301 0.046 Uiso 1 1 calc GR . . . .
C13 C 0.14964(15) 0.67326(12) 0.19318(10) 0.0192(3) Uani 1 1 d . . . . .
H13 H 0.1405 0.6466 0.2561 0.023 Uiso 1 1 calc R . . . .
C14 C -0.00697(19) 0.66637(17) 0.12373(15) 0.0455(5) Uani 1 1 d . . . . .
H14A H -0.0046 0.6932 0.0609 0.068 Uiso 1 1 calc GR . . . .
H14B H -0.0759 0.7106 0.1477 0.068 Uiso 1 1 calc GR . . . .
H14C H -0.0407 0.5909 0.1181 0.068 Uiso 1 1 calc GR . . . .
C15 C 0.20024(18) 0.79107(12) 0.20876(11) 0.0266(3) Uani 1 1 d . . . . .
H15A H 0.3018 0.7939 0.2517 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.1325 0.8310 0.2372 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.1989 0.8239 0.1473 0.040 Uiso 1 1 calc GR . . . .


_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 1.7380(13) . ?
S1 C3 1.7231(13) . ?
Si1 C1 1.8931(14) . ?
Si1 C7 1.8891(15) . ?
Si1 C10 1.8900(14) . ?
Si1 C13 1.8830(14) . ?
F1 C6 1.290(2) . ?
N1 C1 1.3181(18) . ?
N1 C2 1.3698(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3640(19) . ?
C3 C4 1.4659(18) . ?
C4 C5 1.4012(19) . ?
C4 C6 1.398(2) 3_766 ?
C5 H5 0.9500 . ?
C5 C6 1.3816(19) . ?
C6 C4 1.398(2) 3_766 ?
C7 H7 1.0000 . ?
C7 C8 1.531(2) . ?
C7 C9 1.531(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.534(2) . ?
C10 C12 1.534(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.531(2) . ?
C13 C15 1.527(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C3 S1 C1 90.80(6) . . ?
C7 Si1 C1 106.40(6) . . ?
C7 Si1 C10 109.31(7) . . ?
C10 Si1 C1 107.57(6) . . ?
C13 Si1 C1 105.63(6) . . ?
C13 Si1 C7 117.16(7) . . ?
C13 Si1 C10 110.25(6) . . ?
C1 N1 C2 111.17(11) . . ?
S1 C1 Si1 122.39(8) . . ?
N1 C1 S1 112.87(10) . . ?
N1 C1 Si1 124.62(10) . . ?
N1 C2 H2 121.5 . . ?
C3 C2 N1 116.97(12) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 S1 108.17(10) . . ?
C2 C3 C4 127.33(12) . . ?
C4 C3 S1 124.43(10) . . ?
C5 C4 C3 120.06(12) . . ?
C6 C4 C3 122.49(12) 3_766 . ?
C6 C4 C5 117.45(13) 3_766 . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.93(13) . . ?
C6 C5 H5 120.0 . . ?
F1 C6 C4 117.88(14) . 3_766 ?
F1 C6 C5 119.50(14) . . ?
C5 C6 C4 122.63(13) . 3_766 ?
Si1 C7 H7 106.0 . . ?
C8 C7 Si1 115.91(11) . . ?
C8 C7 H7 106.0 . . ?
C8 C7 C9 109.80(14) . . ?
C9 C7 Si1 112.39(12) . . ?
C9 C7 H7 106.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C10 H10 107.2 . . ?
C11 C10 Si1 112.99(10) . . ?
C11 C10 H10 107.2 . . ?
C11 C10 C12 110.29(13) . . ?
C12 C10 Si1 111.76(10) . . ?
C12 C10 H10 107.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13 106.2 . . ?
C14 C13 Si1 114.47(10) . . ?
C14 C13 H13 106.2 . . ?
C15 C13 Si1 112.63(10) . . ?
C15 C13 H13 106.2 . . ?
C15 C13 C14 110.49(13) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C3 C4 C5 -151.51(11) . . . . ?
S1 C3 C4 C6 27.33(19) . . . 3_766 ?
N1 C2 C3 S1 1.21(15) . . . . ?
N1 C2 C3 C4 -175.98(12) . . . . ?
C1 S1 C3 C2 -1.00(10) . . . . ?
C1 S1 C3 C4 176.29(12) . . . . ?
C1 Si1 C7 C8 -58.00(13) . . . . ?
C1 Si1 C7 C9 174.58(15) . . . . ?
C1 Si1 C10 C11 -66.10(12) . . . . ?
C1 Si1 C10 C12 58.99(12) . . . . ?
C1 Si1 C13 C14 -164.19(13) . . . . ?
C1 Si1 C13 C15 68.48(11) . . . . ?
C1 N1 C2 C3 -0.75(17) . . . . ?
C2 N1 C1 S1 -0.09(14) . . . . ?
C2 N1 C1 Si1 176.00(10) . . . . ?
C2 C3 C4 C5 25.3(2) . . . . ?
C2 C3 C4 C6 -155.90(14) . . . 3_766 ?
C3 S1 C1 Si1 -175.54(8) . . . . ?
C3 S1 C1 N1 0.65(11) . . . . ?
C3 C4 C5 C6 179.23(12) . . . . ?
C4 C5 C6 F1 179.58(15) . . . . ?
C4 C5 C6 C4 -0.4(2) . . . 3_766 ?
C6 C4 C5 C6 0.3(2) 3_766 . . . ?
C7 Si1 C1 S1 -27.23(10) . . . . ?
C7 Si1 C1 N1 157.04(12) . . . . ?
C7 Si1 C10 C11 49.04(13) . . . . ?
C7 Si1 C10 C12 174.13(11) . . . . ?
C7 Si1 C13 C14 77.58(15) . . . . ?
C7 Si1 C13 C15 -49.75(12) . . . . ?
C10 Si1 C1 S1 89.83(9) . . . . ?
C10 Si1 C1 N1 -85.91(12) . . . . ?
C10 Si1 C7 C8 -173.89(11) . . . . ?
C10 Si1 C7 C9 58.69(16) . . . . ?
C10 Si1 C13 C14 -48.25(15) . . . . ?
C10 Si1 C13 C15 -175.58(10) . . . . ?
C13 Si1 C1 S1 -152.42(8) . . . . ?
C13 Si1 C1 N1 31.84(13) . . . . ?
C13 Si1 C7 C8 59.81(14) . . . . ?
C13 Si1 C7 C9 -67.61(16) . . . . ?
C13 Si1 C10 C11 179.19(11) . . . . ?
C13 Si1 C10 C12 -55.72(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xj0f
_database_code_depnum_ccdc_archive 'CCDC 1856895'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2016-12-20
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H48 N2 S2 Si2'
_chemical_formula_sum            'C30 H48 N2 S2 Si2'
_chemical_formula_weight         557.00
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.2882(2)
_cell_length_b                   12.3511(3)
_cell_length_c                   14.5307(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.8260(10)
_cell_angle_gamma                90
_cell_volume                     1603.77(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.138
_cell_measurement_theta_min      4.777
_shelx_estimated_absorpt_T_max   0.841
_shelx_estimated_absorpt_T_min   0.290
_exptl_absorpt_coefficient_mu    2.364
_exptl_absorpt_correction_T_max  0.5707
_exptl_absorpt_correction_T_min  0.2419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1229 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.4239.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.695
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.076
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15613
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.133
_diffrn_reflns_theta_min         4.777
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2676
_reflns_number_total             3032
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3032
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+0.8862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0915
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.63833(4) 0.44990(4) 0.26938(3) 0.02067(13) Uani 1 1 d . . . . .
Si1 Si 0.29203(5) 0.41797(4) 0.16231(3) 0.01669(13) Uani 1 1 d . . . . .
N1 N 0.44291(15) 0.41847(12) 0.36110(11) 0.0208(3) Uani 1 1 d . . . . .
C1 C 0.45568(18) 0.42492(13) 0.27333(12) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.57853(18) 0.43348(14) 0.42709(12) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.5883 0.4306 0.4938 0.024 Uiso 1 1 calc R . . . .
C3 C 0.69843(18) 0.45268(13) 0.39260(12) 0.0176(3) Uani 1 1 d . . . . .
C4 C 0.85284(18) 0.47576(13) 0.44716(12) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.88107(19) 0.52422(14) 0.53760(12) 0.0205(4) Uani 1 1 d . . . . .
H5 H 0.8001 0.5411 0.5634 0.025 Uiso 1 1 calc R . . . .
C6 C 1.02582(19) 0.54756(14) 0.58931(13) 0.0203(4) Uani 1 1 d . . . . .
H6 H 1.0434 0.5800 0.6507 0.024 Uiso 1 1 calc R . . . .
C7 C 0.3680(2) 0.36564(15) 0.06291(13) 0.0257(4) Uani 1 1 d . . . . .
H7 H 0.4432 0.4203 0.0550 0.031 Uiso 1 1 calc R . . . .
C8 C 0.4519(2) 0.25723(16) 0.08211(16) 0.0339(5) Uani 1 1 d . . . . .
H8A H 0.5240 0.2591 0.1454 0.051 Uiso 1 1 calc GR . . . .
H8B H 0.5049 0.2450 0.0333 0.051 Uiso 1 1 calc GR . . . .
H8C H 0.3801 0.1985 0.0799 0.051 Uiso 1 1 calc GR . . . .
C9 C 0.2490(3) 0.3610(3) -0.03309(17) 0.0576(8) Uani 1 1 d . . . . .
H9A H 0.1706 0.3097 -0.0290 0.086 Uiso 1 1 calc GR . . . .
H9B H 0.2950 0.3374 -0.0829 0.086 Uiso 1 1 calc GR . . . .
H9C H 0.2051 0.4331 -0.0491 0.086 Uiso 1 1 calc GR . . . .
C10 C 0.14686(18) 0.33206(15) 0.19703(13) 0.0227(4) Uani 1 1 d . . . . .
H10 H 0.1421 0.3584 0.2612 0.027 Uiso 1 1 calc R . . . .
C11 C 0.1923(2) 0.21331(16) 0.20964(15) 0.0305(4) Uani 1 1 d . . . . .
H11A H 0.1863 0.1813 0.1470 0.046 Uiso 1 1 calc GR . . . .
H11B H 0.1246 0.1746 0.2395 0.046 Uiso 1 1 calc GR . . . .
H11C H 0.2951 0.2077 0.2505 0.046 Uiso 1 1 calc GR . . . .
C12 C -0.0114(2) 0.3431(2) 0.13036(18) 0.0448(6) Uani 1 1 d . . . . .
H12A H -0.0415 0.4194 0.1261 0.067 Uiso 1 1 calc GR . . . .
H12B H -0.0811 0.3006 0.1557 0.067 Uiso 1 1 calc GR . . . .
H12C H -0.0131 0.3164 0.0666 0.067 Uiso 1 1 calc GR . . . .
C13 C 0.21907(19) 0.56033(14) 0.13318(13) 0.0229(4) Uani 1 1 d . . . . .
H13 H 0.1275 0.5551 0.0779 0.028 Uiso 1 1 calc R . . . .
C14 C 0.1715(2) 0.61153(17) 0.21621(16) 0.0355(5) Uani 1 1 d . . . . .
H14A H 0.0958 0.5658 0.2325 0.053 Uiso 1 1 calc GR . . . .
H14B H 0.1294 0.6835 0.1973 0.053 Uiso 1 1 calc GR . . . .
H14C H 0.2587 0.6180 0.2719 0.053 Uiso 1 1 calc GR . . . .
C15 C 0.3300(2) 0.63461(16) 0.10222(17) 0.0350(5) Uani 1 1 d . . . . .
H15A H 0.4226 0.6400 0.1541 0.053 Uiso 1 1 calc GR . . . .
H15B H 0.2859 0.7068 0.0875 0.053 Uiso 1 1 calc GR . . . .
H15C H 0.3522 0.6045 0.0452 0.053 Uiso 1 1 calc GR . . . .


_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 1.7406(16) . ?
S1 C3 1.7244(17) . ?
Si1 C1 1.8928(17) . ?
Si1 C7 1.8864(18) . ?
Si1 C10 1.8893(17) . ?
Si1 C13 1.8905(18) . ?
N1 C1 1.315(2) . ?
N1 C2 1.372(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.361(2) . ?
C3 C4 1.465(2) . ?
C4 C5 1.402(2) . ?
C4 C6 1.400(2) 3_766 ?
C5 H5 0.9500 . ?
C5 C6 1.380(2) . ?
C6 C4 1.400(2) 3_766 ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.536(3) . ?
C7 C9 1.526(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.523(3) . ?
C10 C12 1.530(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.530(3) . ?
C13 C15 1.535(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C3 S1 C1 90.67(8) . . ?
C7 Si1 C1 106.67(8) . . ?
C7 Si1 C10 117.09(9) . . ?
C7 Si1 C13 109.47(8) . . ?
C10 Si1 C1 105.29(8) . . ?
C10 Si1 C13 110.11(8) . . ?
C13 Si1 C1 107.71(8) . . ?
C1 N1 C2 111.17(14) . . ?
S1 C1 Si1 122.92(10) . . ?
N1 C1 S1 112.90(12) . . ?
N1 C1 Si1 124.05(12) . . ?
N1 C2 H2 121.5 . . ?
C3 C2 N1 116.99(16) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 S1 108.25(13) . . ?
C2 C3 C4 127.83(16) . . ?
C4 C3 S1 123.89(13) . . ?
C5 C4 C3 119.70(15) . . ?
C6 C4 C3 121.71(16) 3_766 . ?
C6 C4 C5 118.59(15) 3_766 . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.32(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C6 H6 119.5 3_766 . ?
C5 C6 C4 121.09(16) . 3_766 ?
C5 C6 H6 119.5 . . ?
Si1 C7 H7 105.9 . . ?
C8 C7 Si1 115.89(13) . . ?
C8 C7 H7 105.9 . . ?
C9 C7 Si1 112.56(14) . . ?
C9 C7 H7 105.9 . . ?
C9 C7 C8 109.78(17) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C10 H10 106.4 . . ?
C11 C10 Si1 112.24(12) . . ?
C11 C10 H10 106.4 . . ?
C11 C10 C12 110.41(16) . . ?
C12 C10 Si1 114.42(13) . . ?
C12 C10 H10 106.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13 107.1 . . ?
C14 C13 Si1 111.76(13) . . ?
C14 C13 H13 107.1 . . ?
C14 C13 C15 110.20(16) . . ?
C15 C13 Si1 113.15(12) . . ?
C15 C13 H13 107.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C3 C4 C5 150.93(14) . . . . ?
S1 C3 C4 C6 -27.9(2) . . . 3_766 ?
N1 C2 C3 S1 -0.91(19) . . . . ?
N1 C2 C3 C4 177.19(16) . . . . ?
C1 S1 C3 C2 0.76(13) . . . . ?
C1 S1 C3 C4 -177.43(15) . . . . ?
C1 Si1 C7 C8 55.35(16) . . . . ?
C1 Si1 C7 C9 -177.14(17) . . . . ?
C1 Si1 C10 C11 -71.03(14) . . . . ?
C1 Si1 C10 C12 162.15(16) . . . . ?
C1 Si1 C13 C14 -58.22(15) . . . . ?
C1 Si1 C13 C15 66.88(16) . . . . ?
C1 N1 C2 C3 0.6(2) . . . . ?
C2 N1 C1 S1 0.09(18) . . . . ?
C2 N1 C1 Si1 -175.79(12) . . . . ?
C2 C3 C4 C5 -26.9(3) . . . . ?
C2 C3 C4 C6 154.27(18) . . . 3_766 ?
C3 S1 C1 Si1 175.43(11) . . . . ?
C3 S1 C1 N1 -0.51(13) . . . . ?
C3 C4 C5 C6 -179.25(16) . . . . ?
C4 C5 C6 C4 0.4(3) . . . 3_766 ?
C6 C4 C5 C6 -0.4(3) 3_766 . . . ?
C7 Si1 C1 S1 30.63(13) . . . . ?
C7 Si1 C1 N1 -153.89(14) . . . . ?
C7 Si1 C10 C11 47.25(16) . . . . ?
C7 Si1 C10 C12 -79.57(18) . . . . ?
C7 Si1 C13 C14 -173.84(13) . . . . ?
C7 Si1 C13 C15 -48.74(16) . . . . ?
C10 Si1 C1 S1 155.70(10) . . . . ?
C10 Si1 C1 N1 -28.81(16) . . . . ?
C10 Si1 C7 C8 -62.19(17) . . . . ?
C10 Si1 C7 C9 65.33(19) . . . . ?
C10 Si1 C13 C14 56.08(15) . . . . ?
C10 Si1 C13 C15 -178.82(14) . . . . ?
C13 Si1 C1 S1 -86.82(11) . . . . ?
C13 Si1 C1 N1 88.67(15) . . . . ?
C13 Si1 C7 C8 171.62(14) . . . . ?
C13 Si1 C7 C9 -60.87(19) . . . . ?
C13 Si1 C10 C11 173.13(13) . . . . ?
C13 Si1 C10 C12 46.31(18) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_f4r
_database_code_depnum_ccdc_archive 'CCDC 1856887'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2017-05-31
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H2 F2 N S)'
_chemical_formula_sum            'C12 H4 F4 N2 S2'
_chemical_formula_weight         316.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

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

_cell_length_a                   5.0225(8)
_cell_length_b                   7.1949(14)
_cell_length_c                   17.290(3)
_cell_angle_alpha                84.549(3)
_cell_angle_beta                 83.096(2)
_cell_angle_gamma                70.873(2)
_cell_volume                     584.98(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4388
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.475
_cell_measurement_theta_min      2.377
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.785
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0472 before and 0.0254 after correction. The Ratio of minimum to maximum transmission is 0.9073. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.437
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6854
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         1.188
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2458
_reflns_number_total             2659
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+0.3166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0681
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C2B(H2B), C3(H3), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.73124(8) -0.36196(5) 0.59085(2) 0.02162(10) Uani 1 1 d . . . . .
S1B S 0.59756(7) 0.30387(6) 0.81444(2) 0.02208(10) Uani 1 1 d . . . . .
F1B F 0.08835(16) 0.58817(12) 0.84578(4) 0.02155(19) Uani 1 1 d . . . . .
F2B F -0.39149(16) 0.77434(12) 0.91886(5) 0.02227(19) Uani 1 1 d . . . . .
F2 F 1.09449(17) -0.15550(12) 0.35897(5) 0.02170(18) Uani 1 1 d . . . . .
F1 F 1.48231(17) -0.28513(12) 0.45497(5) 0.02133(18) Uani 1 1 d . . . . .
N1B N 0.7491(2) 0.16740(18) 0.95032(7) 0.0194(2) Uani 1 1 d . . . . .
N1 N 1.4220(3) -0.08305(19) 0.67602(7) 0.0220(3) Uani 1 1 d . . . . .
C5B C 0.0508(3) 0.5404(2) 0.92275(7) 0.0160(3) Uani 1 1 d . . . . .
C4B C 0.2667(3) 0.39524(19) 0.95838(7) 0.0149(2) Uani 1 1 d . . . . .
C1B C 0.5358(3) 0.28708(19) 0.91559(7) 0.0147(2) Uani 1 1 d . . . . .
C4 C 1.2166(3) -0.07580(19) 0.55371(7) 0.0163(3) Uani 1 1 d . . . . .
C6B C -0.2049(3) 0.64067(19) 0.96178(8) 0.0158(3) Uani 1 1 d . . . . .
C6 C 1.0376(3) -0.0739(2) 0.42787(7) 0.0169(3) Uani 1 1 d . . . . .
C1 C 1.4349(3) -0.15660(19) 0.60864(7) 0.0164(3) Uani 1 1 d . . . . .
C5 C 1.2433(3) -0.14407(19) 0.47948(8) 0.0167(3) Uani 1 1 d . . . . .
C3B C 0.9288(3) 0.1396(2) 0.82090(8) 0.0192(3) Uani 1 1 d . . . . .
H3B H 1.0635 0.0938 0.7777 0.023 Uiso 1 1 calc R . . . .
C2B C 0.9712(3) 0.0840(2) 0.89685(8) 0.0200(3) Uani 1 1 d . . . . .
H2B H 1.1443 -0.0071 0.9120 0.024 Uiso 1 1 calc R . . . .
C3 C 1.8376(3) -0.3440(2) 0.67913(8) 0.0229(3) Uani 1 1 d . . . . .
H3 H 2.0045 -0.4302 0.6997 0.027 Uiso 1 1 calc R . . . .
C2 C 1.6496(3) -0.1892(2) 0.71563(8) 0.0237(3) Uani 1 1 d . . . . .
H2 H 1.6740 -0.1562 0.7656 0.028 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 1.7402(14) . ?
S1 C3 1.7059(15) . ?
S1B C1B 1.7388(13) . ?
S1B C3B 1.7052(14) . ?
F1B C5B 1.3491(15) . ?
F2B C6B 1.3397(14) . ?
F2 C6 1.3366(15) . ?
F1 C5 1.3459(15) . ?
N1B C1B 1.3045(17) . ?
N1B C2B 1.3704(17) . ?
N1 C1 1.3108(18) . ?
N1 C2 1.3693(19) . ?
C5B C4B 1.3934(18) . ?
C5B C6B 1.3793(18) . ?
C4B C1B 1.4696(17) . ?
C4B C6B 1.3967(18) 2_567 ?
C4 C6 1.3995(19) 2_756 ?
C4 C1 1.4728(18) . ?
C4 C5 1.3934(18) . ?
C6B C4B 1.3966(18) 2_567 ?
C6 C4 1.3995(19) 2_756 ?
C6 C5 1.3829(19) . ?
C3B H3B 0.9500 . ?
C3B C2B 1.3569(19) . ?
C2B H2B 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.353(2) . ?
C2 H2 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
C3 S1 C1 89.51(7) . . ?
C3B S1B C1B 89.52(6) . . ?
C1B N1B C2B 110.77(12) . . ?
C1 N1 C2 110.86(12) . . ?
F1B C5B C4B 119.45(11) . . ?
F1B C5B C6B 116.85(11) . . ?
C6B C5B C4B 123.71(12) . . ?
C5B C4B C1B 122.99(12) . . ?
C5B C4B C6B 114.37(11) . 2_567 ?
C6B C4B C1B 122.64(12) 2_567 . ?
N1B C1B S1B 113.93(10) . . ?
N1B C1B C4B 122.78(12) . . ?
C4B C1B S1B 123.29(10) . . ?
C6 C4 C1 122.84(12) 2_756 . ?
C5 C4 C6 114.23(12) . 2_756 ?
C5 C4 C1 122.93(12) . . ?
F2B C6B C5B 116.35(12) . . ?
F2B C6B C4B 121.73(11) . 2_567 ?
C5B C6B C4B 121.92(12) . 2_567 ?
F2 C6 C4 121.44(12) . 2_756 ?
F2 C6 C5 116.60(12) . . ?
C5 C6 C4 121.96(12) . 2_756 ?
N1 C1 S1 113.64(10) . . ?
N1 C1 C4 123.31(12) . . ?
C4 C1 S1 123.04(10) . . ?
F1 C5 C4 119.28(12) . . ?
F1 C5 C6 116.91(12) . . ?
C6 C5 C4 123.81(13) . . ?
S1B C3B H3B 125.1 . . ?
C2B C3B S1B 109.90(10) . . ?
C2B C3B H3B 125.1 . . ?
N1B C2B H2B 122.1 . . ?
C3B C2B N1B 115.88(12) . . ?
C3B C2B H2B 122.1 . . ?
S1 C3 H3 124.9 . . ?
C2 C3 S1 110.12(11) . . ?
C2 C3 H3 124.9 . . ?
N1 C2 H2 122.1 . . ?
C3 C2 N1 115.87(13) . . ?
C3 C2 H2 122.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C3 C2 N1 0.03(17) . . . . ?
S1B C3B C2B N1B 0.07(17) . . . . ?
F1B C5B C4B C1B -1.1(2) . . . . ?
F1B C5B C4B C6B 179.52(12) . . . 2_567 ?
F1B C5B C6B F2B 0.67(18) . . . . ?
F1B C5B C6B C4B -179.48(12) . . . 2_567 ?
F2 C6 C5 F1 1.04(18) . . . . ?
F2 C6 C5 C4 -179.60(12) . . . . ?
C5B C4B C1B S1B -8.78(19) . . . . ?
C5B C4B C1B N1B 172.16(13) . . . . ?
C4B C5B C6B F2B -179.25(12) . . . . ?
C4B C5B C6B C4B 0.6(2) . . . 2_567 ?
C1B S1B C3B C2B -0.08(11) . . . . ?
C1B N1B C2B C3B 0.00(19) . . . . ?
C4 C6 C5 F1 -178.51(11) 2_756 . . . ?
C4 C6 C5 C4 0.9(2) 2_756 . . . ?
C6B C5B C4B C1B 178.78(13) . . . . ?
C6B C5B C4B C6B -0.6(2) . . . 2_567 ?
C6B C4B C1B S1B 170.50(11) 2_567 . . . ?
C6B C4B C1B N1B -8.6(2) 2_567 . . . ?
C6 C4 C1 S1 172.02(10) 2_756 . . . ?
C6 C4 C1 N1 -6.7(2) 2_756 . . . ?
C6 C4 C5 F1 178.56(11) 2_756 . . . ?
C6 C4 C5 C6 -0.8(2) 2_756 . . . ?
C1 S1 C3 C2 -0.04(12) . . . . ?
C1 N1 C2 C3 0.01(19) . . . . ?
C1 C4 C5 F1 -2.5(2) . . . . ?
C1 C4 C5 C6 178.16(12) . . . . ?
C5 C4 C1 S1 -6.85(19) . . . . ?
C5 C4 C1 N1 174.38(13) . . . . ?
C3B S1B C1B N1B 0.09(11) . . . . ?
C3B S1B C1B C4B -179.04(12) . . . . ?
C2B N1B C1B S1B -0.07(16) . . . . ?
C2B N1B C1B C4B 179.07(12) . . . . ?
C3 S1 C1 N1 0.05(11) . . . . ?
C3 S1 C1 C4 -178.83(12) . . . . ?
C2 N1 C1 S1 -0.04(15) . . . . ?
C2 N1 C1 C4 178.83(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xj2f
_database_code_depnum_ccdc_archive 'CCDC 1856897'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2016-12-20
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H46 F2 N2 S2 Si2'
_chemical_formula_sum            'C30 H46 F2 N2 S2 Si2'
_chemical_formula_weight         592.99
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3622(3)
_cell_length_b                   12.3591(4)
_cell_length_c                   14.6437(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.6740(10)
_cell_angle_gamma                90
_cell_volume                     1623.15(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.10
_cell_measurement_theta_min      4.77
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.491
_exptl_absorpt_coefficient_mu    2.458
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1069 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.7718.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.047
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26658
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.187
_diffrn_reflns_theta_min         4.768
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2840
_reflns_number_total             3087
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²+0.6503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0738
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.36438(3) 0.55864(3) 0.23133(2) 0.01590(10) Uani 1 1 d . . . . .
Si1 Si 0.70797(4) 0.58551(3) 0.33974(2) 0.01269(10) Uani 1 1 d . . . . .
F1 F 0.04941(9) 0.59631(7) 0.17195(6) 0.0254(2) Uani 1 1 d . . . . .
N1 N 0.55786(12) 0.58005(9) 0.13973(8) 0.0169(2) Uani 1 1 d . . . . .
C1 C 0.54600(14) 0.57762(10) 0.22731(9) 0.0140(3) Uani 1 1 d . . . . .
C2 C 0.42146(14) 0.56584(11) 0.07408(9) 0.0156(3) Uani 1 1 d . . . . .
H2 H 0.4105 0.5662 0.0076 0.019 Uiso 1 1 calc R . . . .
C3 C 0.30219(14) 0.55114(10) 0.10867(9) 0.0138(3) Uani 1 1 d . . . . .
C4 C 0.14851(14) 0.52633(10) 0.05343(9) 0.0140(3) Uani 1 1 d . . . . .
C5 C 0.02547(15) 0.54748(11) 0.08597(9) 0.0162(3) Uani 1 1 d . . . . .
C6 C -0.11932(14) 0.52347(11) 0.03603(9) 0.0160(3) Uani 1 1 d . . . . .
H6 H -0.1987 0.5405 0.0619 0.019 Uiso 1 1 calc R . . . .
C7 C 0.62646(15) 0.62773(12) 0.43821(9) 0.0205(3) Uani 1 1 d . . . . .
H7 H 0.5472 0.5734 0.4379 0.025 Uiso 1 1 calc R . . . .
C8 C 0.54892(18) 0.73847(13) 0.42592(12) 0.0287(3) Uani 1 1 d . . . . .
H8A H 0.6241 0.7959 0.4366 0.043 Uiso 1 1 calc GR . . . .
H8B H 0.4917 0.7456 0.4721 0.043 Uiso 1 1 calc GR . . . .
H8C H 0.4815 0.7445 0.3611 0.043 Uiso 1 1 calc GR . . . .
C9 C 0.7394(2) 0.6200(2) 0.53714(11) 0.0481(5) Uani 1 1 d . . . . .
H9A H 0.7822 0.5470 0.5465 0.072 Uiso 1 1 calc GR . . . .
H9B H 0.6892 0.6348 0.5860 0.072 Uiso 1 1 calc GR . . . .
H9C H 0.8191 0.6730 0.5422 0.072 Uiso 1 1 calc GR . . . .
C10 C 0.78799(15) 0.44457(11) 0.36477(10) 0.0185(3) Uani 1 1 d . . . . .
H10 H 0.8768 0.4496 0.4222 0.022 Uiso 1 1 calc R . . . .
C11 C 0.67861(18) 0.36453(12) 0.38901(12) 0.0299(3) Uani 1 1 d . . . . .
H11A H 0.6494 0.3914 0.4440 0.045 Uiso 1 1 calc GR . . . .
H11B H 0.7268 0.2938 0.4043 0.045 Uiso 1 1 calc GR . . . .
H11C H 0.5899 0.3573 0.3341 0.045 Uiso 1 1 calc GR . . . .
C12 C 0.84299(18) 0.40075(12) 0.28297(12) 0.0283(3) Uani 1 1 d . . . . .
H12A H 0.7589 0.3956 0.2250 0.042 Uiso 1 1 calc GR . . . .
H12B H 0.8867 0.3288 0.2998 0.042 Uiso 1 1 calc GR . . . .
H12C H 0.9185 0.4498 0.2717 0.042 Uiso 1 1 calc GR . . . .
C13 C 0.84754(14) 0.67916(11) 0.31113(9) 0.0168(3) Uani 1 1 d . . . . .
H13 H 0.8624 0.6521 0.2502 0.020 Uiso 1 1 calc R . . . .
C14 C 1.00182(17) 0.67804(15) 0.38428(13) 0.0381(4) Uani 1 1 d . . . . .
H14A H 0.9944 0.7072 0.4450 0.057 Uiso 1 1 calc GR . . . .
H14B H 1.0706 0.7226 0.3610 0.057 Uiso 1 1 calc GR . . . .
H14C H 1.0392 0.6036 0.3937 0.057 Uiso 1 1 calc GR . . . .
C15 C 0.79017(16) 0.79516(12) 0.29144(11) 0.0244(3) Uani 1 1 d . . . . .
H15A H 0.6901 0.7943 0.2462 0.037 Uiso 1 1 calc GR . . . .
H15B H 0.8576 0.8365 0.2643 0.037 Uiso 1 1 calc GR . . . .
H15C H 0.7861 0.8290 0.3512 0.037 Uiso 1 1 calc GR . . . .


_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 1.7341(13) . ?
S1 C3 1.7244(13) . ?
Si1 C1 1.8939(13) . ?
Si1 C7 1.8883(14) . ?
Si1 C10 1.8901(14) . ?
Si1 C13 1.8806(13) . ?
F1 C5 1.3557(15) . ?
N1 C1 1.3190(17) . ?
N1 C2 1.3716(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.3642(18) . ?
C3 C4 1.4665(17) . ?
C4 C5 1.3919(18) . ?
C4 C6 1.4014(18) 3_565 ?
C5 C6 1.3753(18) . ?
C6 C4 1.4014(18) 3_565 ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.535(2) . ?
C7 C9 1.532(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.5368(19) . ?
C10 C12 1.532(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.5316(18) . ?
C13 C15 1.5291(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C3 S1 C1 90.76(6) . . ?
C7 Si1 C1 106.25(6) . . ?
C7 Si1 C10 109.34(6) . . ?
C10 Si1 C1 107.16(6) . . ?
C13 Si1 C1 105.80(6) . . ?
C13 Si1 C7 117.32(6) . . ?
C13 Si1 C10 110.38(6) . . ?
C1 N1 C2 110.94(11) . . ?
S1 C1 Si1 121.72(7) . . ?
N1 C1 S1 113.14(10) . . ?
N1 C1 Si1 125.05(10) . . ?
N1 C2 H2 121.5 . . ?
C3 C2 N1 116.96(12) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 S1 108.17(9) . . ?
C2 C3 C4 126.94(12) . . ?
C4 C3 S1 124.78(10) . . ?
C5 C4 C3 123.31(12) . . ?
C5 C4 C6 116.35(12) . 3_565 ?
C6 C4 C3 120.32(11) 3_565 . ?
F1 C5 C4 117.97(11) . . ?
F1 C5 C6 117.71(11) . . ?
C6 C5 C4 124.31(12) . . ?
C4 C6 H6 120.3 3_565 . ?
C5 C6 C4 119.33(12) . 3_565 ?
C5 C6 H6 120.3 . . ?
Si1 C7 H7 105.8 . . ?
C8 C7 Si1 115.96(10) . . ?
C8 C7 H7 105.8 . . ?
C9 C7 Si1 112.59(10) . . ?
C9 C7 H7 105.8 . . ?
C9 C7 C8 109.98(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
Si1 C10 H10 107.1 . . ?
C11 C10 Si1 112.62(10) . . ?
C11 C10 H10 107.1 . . ?
C12 C10 Si1 112.18(10) . . ?
C12 C10 H10 107.1 . . ?
C12 C10 C11 110.41(12) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Si1 C13 H13 106.1 . . ?
C14 C13 Si1 114.51(10) . . ?
C14 C13 H13 106.1 . . ?
C15 C13 Si1 112.96(9) . . ?
C15 C13 H13 106.1 . . ?
C15 C13 C14 110.49(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C3 C4 C5 26.42(18) . . . . ?
S1 C3 C4 C6 -152.04(11) . . . 3_565 ?
F1 C5 C6 C4 179.56(12) . . . 3_565 ?
N1 C2 C3 S1 1.42(15) . . . . ?
N1 C2 C3 C4 -175.01(12) . . . . ?
C1 S1 C3 C2 -1.35(10) . . . . ?
C1 S1 C3 C4 175.18(11) . . . . ?
C1 Si1 C7 C8 -61.47(12) . . . . ?
C1 Si1 C7 C9 170.63(13) . . . . ?
C1 Si1 C10 C11 -65.46(12) . . . . ?
C1 Si1 C10 C12 59.85(11) . . . . ?
C1 Si1 C13 C14 -167.18(12) . . . . ?
C1 Si1 C13 C15 65.16(11) . . . . ?
C1 N1 C2 C3 -0.64(17) . . . . ?
C2 N1 C1 S1 -0.48(14) . . . . ?
C2 N1 C1 Si1 176.14(9) . . . . ?
C2 C3 C4 C5 -157.71(13) . . . . ?
C2 C3 C4 C6 23.8(2) . . . 3_565 ?
C3 S1 C1 Si1 -175.66(8) . . . . ?
C3 S1 C1 N1 1.09(10) . . . . ?
C3 C4 C5 F1 1.95(19) . . . . ?
C3 C4 C5 C6 -179.00(12) . . . . ?
C4 C5 C6 C4 0.5(2) . . . 3_565 ?
C6 C4 C5 F1 -179.54(11) 3_565 . . . ?
C6 C4 C5 C6 -0.5(2) 3_565 . . . ?
C7 Si1 C1 S1 -23.17(10) . . . . ?
C7 Si1 C1 N1 160.48(11) . . . . ?
C7 Si1 C10 C11 49.30(12) . . . . ?
C7 Si1 C10 C12 174.61(10) . . . . ?
C7 Si1 C13 C14 74.56(13) . . . . ?
C7 Si1 C13 C15 -53.11(12) . . . . ?
C10 Si1 C1 S1 93.64(8) . . . . ?
C10 Si1 C1 N1 -82.72(12) . . . . ?
C10 Si1 C7 C8 -176.81(10) . . . . ?
C10 Si1 C7 C9 55.29(14) . . . . ?
C10 Si1 C13 C14 -51.56(13) . . . . ?
C10 Si1 C13 C15 -179.23(9) . . . . ?
C13 Si1 C1 S1 -148.57(8) . . . . ?
C13 Si1 C1 N1 35.08(13) . . . . ?
C13 Si1 C7 C8 56.55(12) . . . . ?
C13 Si1 C7 C9 -71.34(14) . . . . ?
C13 Si1 C10 C11 179.78(10) . . . . ?
C13 Si1 C10 C12 -54.91(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_f1s
_database_code_depnum_ccdc_archive 'CCDC 1856900'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2018-04-18
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H5 F N2 S2'
_chemical_formula_sum            'C12 H5 F N2 S2'
_chemical_formula_weight         260.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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'

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

_cell_length_a                   3.8093(3)
_cell_length_b                   6.6644(4)
_cell_length_c                   21.5126(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.338(4)
_cell_angle_gamma                90
_cell_volume                     544.57(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5991
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.103
_cell_measurement_theta_min      4.122
_shelx_estimated_absorpt_T_max   0.862
_shelx_estimated_absorpt_T_min   0.815
_exptl_absorpt_coefficient_mu    4.358
_exptl_absorpt_correction_T_max  0.5856
_exptl_absorpt_correction_T_min  0.4198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1319 before and 0.0823 after correction. The Ratio of minimum to maximum transmission is 0.7169. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.049
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8852
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.212
_diffrn_reflns_theta_min         4.122
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                885
_reflns_number_total             1034
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.314
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         1034
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0846
_refine_ls_restrained_S_all      1.313
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+3.4260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1609
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F1A-C2 \\sim F1-C1
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(F1A)
4. Others
 Sof(F1A)=Sof(H1)=0.5*(1-FVAR(2))
 Sof(F1)=Sof(H2)=0.5*FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.8298(4) 0.4397(2) 0.38576(7) 0.0240(4) Uani 1 1 d . . . . .
F1 F 0.698(3) 0.1679(15) 0.6098(4) 0.0224(19) Uani 0.275(5) 1 d D . P A 1
F1A F 0.766(4) 0.3697(15) 0.5061(6) 0.0224(19) Uani 0.225(5) 1 d D . P A 2
N1 N 0.7384(13) 0.2569(8) 0.2811(2) 0.0278(12) Uani 1 1 d . . . . .
C1 C 0.5789(14) 0.0908(8) 0.5569(2) 0.0224(12) Uani 1 1 d D . . . .
H1 H 0.633055 0.156003 0.595764 0.027 Uiso 0.225(5) 1 calc R . P A 2
C2 C 0.6553(14) 0.1857(8) 0.5023(3) 0.0221(12) Uani 1 1 d D . . . .
H2 H 0.764911 0.313795 0.504790 0.026 Uiso 0.275(5) 1 calc R . P A 1
C3 C 0.5773(13) 0.1004(8) 0.4441(2) 0.0192(12) Uani 1 1 d . . . . .
C4 C 0.6627(13) 0.1976(8) 0.3860(2) 0.0182(11) Uani 1 1 d . . . . .
C5 C 0.6366(15) 0.1297(9) 0.3267(3) 0.0252(13) Uani 1 1 d . . . . .
H5 H 0.551010 -0.001269 0.316799 0.030 Uiso 1 1 calc R . . . .
C6 C 0.8478(14) 0.4262(9) 0.3066(3) 0.0270(13) Uani 1 1 d . . . . .
H6 H 0.931226 0.533977 0.282802 0.032 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 C4 1.735(6) . ?
S1 C6 1.713(6) . ?
F1 C1 1.297(9) . ?
F1A C2 1.297(9) . ?
N1 C5 1.373(7) . ?
N1 C6 1.309(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(8) . ?
C1 C3 1.406(8) 3_656 ?
C2 H2 0.9500 . ?
C2 C3 1.387(7) . ?
C3 C4 1.465(7) . ?
C4 C5 1.351(8) . ?
C5 H5 0.9500 . ?
C6 H6 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
C6 S1 C4 89.8(3) . . ?
C6 N1 C5 109.4(5) . . ?
F1 C1 C2 118.8(7) . . ?
F1 C1 C3 119.4(7) . 3_656 ?
C2 C1 H1 119.4 . . ?
C2 C1 C3 121.1(5) . 3_656 ?
C3 C1 H1 119.4 3_656 . ?
F1A C2 C1 117.8(8) . . ?
F1A C2 C3 119.4(8) . . ?
C1 C2 H2 118.8 . . ?
C1 C2 C3 122.3(5) . . ?
C3 C2 H2 118.8 . . ?
C1 C3 C4 120.6(5) 3_656 . ?
C2 C3 C1 116.5(5) . 3_656 ?
C2 C3 C4 122.9(5) . . ?
C3 C4 S1 121.3(4) . . ?
C5 C4 S1 108.0(4) . . ?
C5 C4 C3 130.7(5) . . ?
N1 C5 H5 121.2 . . ?
C4 C5 N1 117.6(5) . . ?
C4 C5 H5 121.2 . . ?
S1 C6 H6 122.4 . . ?
N1 C6 S1 115.2(4) . . ?
N1 C6 H6 122.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C5 N1 -0.3(6) . . . . ?
F1 C1 C2 C3 171.6(7) . . . . ?
F1A C2 C3 C1 -173.0(9) . . . 3_656 ?
F1A C2 C3 C4 9.3(11) . . . . ?
C1 C2 C3 C1 -1.1(8) . . . 3_656 ?
C1 C2 C3 C4 -178.8(5) . . . . ?
C1 C3 C4 S1 175.9(4) 3_656 . . . ?
C1 C3 C4 C5 -4.5(9) 3_656 . . . ?
C2 C3 C4 S1 -6.5(7) . . . . ?
C2 C3 C4 C5 173.1(5) . . . . ?
C3 C1 C2 F1A 173.1(9) 3_656 . . . ?
C3 C1 C2 C3 1.2(9) 3_656 . . . ?
C3 C4 C5 N1 -180.0(5) . . . . ?
C4 S1 C6 N1 0.2(4) . . . . ?
C5 N1 C6 S1 -0.4(6) . . . . ?
C6 S1 C4 C3 179.7(4) . . . . ?
C6 S1 C4 C5 0.1(4) . . . . ?
C6 N1 C5 C4 0.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4f
_database_code_depnum_ccdc_archive 'CCDC 1856898'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2017-01-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H44 F4 N2 S2 Si2'
_chemical_formula_sum            'C30 H44 F4 N2 S2 Si2'
_chemical_formula_weight         628.97
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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                   19.9633(7)
_cell_length_b                   12.2859(4)
_cell_length_c                   13.3676(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3278.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.124
_cell_measurement_theta_min      4.226
_shelx_estimated_absorpt_T_max   0.841
_shelx_estimated_absorpt_T_min   0.228
_exptl_absorpt_coefficient_mu    2.555
_exptl_absorpt_correction_T_max  0.2751
_exptl_absorpt_correction_T_min  0.1198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1624 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.4355.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.822
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            56562
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        64.996
_diffrn_reflns_theta_max         64.996
_diffrn_reflns_theta_min         4.225
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                5389
_reflns_number_total             5565
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 2477 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.060(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5565
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0222
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²+0.3810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0563
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16), C19(H19), C22(H22), C25(H25), C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C),
 C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.39335(3) 0.42610(5) 0.54864(4) 0.02123(13) Uani 1 1 d . . . . .
S2 S 0.79203(3) 0.56630(5) 0.46493(4) 0.02137(13) Uani 1 1 d . . . . .
Si1 Si 0.23951(3) 0.40045(5) 0.49526(5) 0.01848(14) Uani 1 1 d . . . . .
Si2 Si 0.94215(3) 0.60783(5) 0.53829(5) 0.01825(13) Uani 1 1 d . . . . .
F1 F 0.54322(7) 0.53604(12) 0.31608(10) 0.0247(3) Uani 1 1 d . . . . .
F2 F 0.66618(7) 0.59325(12) 0.35934(11) 0.0269(3) Uani 1 1 d . . . . .
F3 F 0.64023(7) 0.44709(12) 0.68477(10) 0.0237(3) Uani 1 1 d . . . . .
F4 F 0.51793(7) 0.39015(12) 0.64169(10) 0.0245(3) Uani 1 1 d . . . . .
N1 N 0.35412(10) 0.40988(17) 0.36734(16) 0.0228(4) Uani 1 1 d . . . . .
N2 N 0.82055(10) 0.59887(17) 0.64877(16) 0.0231(4) Uani 1 1 d . . . . .
C1 C 0.33114(12) 0.40986(18) 0.45955(19) 0.0200(5) Uani 1 1 d . . . . .
C2 C 0.42202(12) 0.42540(19) 0.36529(19) 0.0221(5) Uani 1 1 d . . . . .
H2 H 0.4462 0.4284 0.3041 0.027 Uiso 1 1 calc R . . . .
C3 C 0.45334(12) 0.43636(19) 0.45571(19) 0.0193(5) Uani 1 1 d . . . . .
C4 C 0.52354(11) 0.46213(18) 0.47720(18) 0.0194(5) Uani 1 1 d . . . . .
C5 C 0.56570(11) 0.51277(18) 0.40815(17) 0.0195(5) Uani 1 1 d . . . . .
C6 C 0.63066(12) 0.5434(2) 0.43129(18) 0.0207(5) Uani 1 1 d . . . . .
C7 C 0.65905(11) 0.52605(18) 0.52482(17) 0.0196(5) Uani 1 1 d . . . . .
C8 C 0.61745(11) 0.47284(19) 0.59327(17) 0.0197(5) Uani 1 1 d . . . . .
C9 C 0.55305(11) 0.44222(19) 0.57036(17) 0.0191(5) Uani 1 1 d . . . . .
C10 C 0.72790(11) 0.55738(18) 0.55110(19) 0.0195(4) Uani 1 1 d . . . . .
C11 C 0.84873(11) 0.59452(18) 0.55966(18) 0.0201(5) Uani 1 1 d . . . . .
C12 C 0.75331(12) 0.5778(2) 0.64429(19) 0.0230(5) Uani 1 1 d . . . . .
H12 H 0.7259 0.5773 0.7024 0.028 Uiso 1 1 calc R . . . .
C13 C 0.23843(12) 0.3459(2) 0.62728(19) 0.0254(5) Uani 1 1 d . . . . .
H13 H 0.2701 0.3921 0.6667 0.030 Uiso 1 1 calc R . . . .
C14 C 0.26523(15) 0.2285(2) 0.6335(2) 0.0383(7) Uani 1 1 d . . . . .
H14A H 0.2335 0.1790 0.6009 0.058 Uiso 1 1 calc GR . . . .
H14B H 0.2705 0.2077 0.7038 0.058 Uiso 1 1 calc GR . . . .
H14C H 0.3087 0.2242 0.5997 0.058 Uiso 1 1 calc GR . . . .
C15 C 0.17015(14) 0.3553(3) 0.6789(2) 0.0357(6) Uani 1 1 d . . . . .
H15A H 0.1549 0.4310 0.6764 0.054 Uiso 1 1 calc GR . . . .
H15B H 0.1742 0.3321 0.7487 0.054 Uiso 1 1 calc GR . . . .
H15C H 0.1377 0.3087 0.6444 0.054 Uiso 1 1 calc GR . . . .
C16 C 0.19732(12) 0.3160(2) 0.39610(18) 0.0225(5) Uani 1 1 d . . . . .
H16 H 0.1969 0.3620 0.3344 0.027 Uiso 1 1 calc R . . . .
C17 C 0.23304(14) 0.2104(2) 0.3669(2) 0.0338(6) Uani 1 1 d . . . . .
H17A H 0.2795 0.2265 0.3482 0.051 Uiso 1 1 calc GR . . . .
H17B H 0.2099 0.1769 0.3100 0.051 Uiso 1 1 calc GR . . . .
H17C H 0.2326 0.1600 0.4237 0.051 Uiso 1 1 calc GR . . . .
C18 C 0.12375(12) 0.2935(2) 0.4208(2) 0.0333(6) Uani 1 1 d . . . . .
H18A H 0.1210 0.2483 0.4811 0.050 Uiso 1 1 calc GR . . . .
H18B H 0.1027 0.2551 0.3647 0.050 Uiso 1 1 calc GR . . . .
H18C H 0.1004 0.3625 0.4324 0.050 Uiso 1 1 calc GR . . . .
C19 C 0.20471(12) 0.5440(2) 0.4933(2) 0.0240(5) Uani 1 1 d . . . . .
H19 H 0.1559 0.5392 0.5094 0.029 Uiso 1 1 calc R . . . .
C20 C 0.21097(13) 0.5965(2) 0.3898(2) 0.0317(6) Uani 1 1 d . . . . .
H20A H 0.2581 0.5972 0.3694 0.048 Uiso 1 1 calc GR . . . .
H20B H 0.1940 0.6713 0.3925 0.048 Uiso 1 1 calc GR . . . .
H20C H 0.1848 0.5546 0.3412 0.048 Uiso 1 1 calc GR . . . .
C21 C 0.23736(14) 0.6169(2) 0.5727(2) 0.0356(6) Uani 1 1 d . . . . .
H21A H 0.2299 0.5857 0.6392 0.053 Uiso 1 1 calc GR . . . .
H21B H 0.2175 0.6898 0.5698 0.053 Uiso 1 1 calc GR . . . .
H21C H 0.2856 0.6220 0.5599 0.053 Uiso 1 1 calc GR . . . .
C22 C 0.95507(12) 0.6745(2) 0.41246(18) 0.0230(5) Uani 1 1 d . . . . .
H22 H 0.9370 0.6230 0.3612 0.028 Uiso 1 1 calc R . . . .
C23 C 0.91764(13) 0.7825(2) 0.3982(2) 0.0295(6) Uani 1 1 d . . . . .
H23A H 0.8697 0.7713 0.4102 0.044 Uiso 1 1 calc GR . . . .
H23B H 0.9243 0.8087 0.3296 0.044 Uiso 1 1 calc GR . . . .
H23C H 0.9349 0.8365 0.4455 0.044 Uiso 1 1 calc GR . . . .
C24 C 1.02984(13) 0.6892(2) 0.3890(2) 0.0337(6) Uani 1 1 d . . . . .
H24A H 1.0498 0.7393 0.4376 0.051 Uiso 1 1 calc GR . . . .
H24B H 1.0350 0.7190 0.3215 0.051 Uiso 1 1 calc GR . . . .
H24C H 1.0525 0.6185 0.3930 0.051 Uiso 1 1 calc GR . . . .
C25 C 0.97501(12) 0.6833(2) 0.65132(18) 0.0222(5) Uani 1 1 d . . . . .
H25 H 0.9565 0.6443 0.7109 0.027 Uiso 1 1 calc R . . . .
C26 C 0.94951(14) 0.8004(2) 0.6593(2) 0.0290(6) Uani 1 1 d . . . . .
H26A H 0.9705 0.8449 0.6071 0.043 Uiso 1 1 calc GR . . . .
H26B H 0.9609 0.8300 0.7252 0.043 Uiso 1 1 calc GR . . . .
H26C H 0.9008 0.8014 0.6505 0.043 Uiso 1 1 calc GR . . . .
C27 C 1.05189(13) 0.6790(2) 0.6626(2) 0.0326(6) Uani 1 1 d . . . . .
H27A H 1.0647 0.7091 0.7278 0.049 Uiso 1 1 calc GR . . . .
H27B H 1.0728 0.7219 0.6092 0.049 Uiso 1 1 calc GR . . . .
H27C H 1.0670 0.6033 0.6580 0.049 Uiso 1 1 calc GR . . . .
C28 C 0.97734(12) 0.46532(19) 0.5357(2) 0.0256(5) Uani 1 1 d . . . . .
H28 H 1.0268 0.4722 0.5254 0.031 Uiso 1 1 calc R . . . .
C29 C 0.96707(15) 0.4056(2) 0.6358(2) 0.0364(6) Uani 1 1 d . . . . .
H29A H 0.9884 0.4471 0.6897 0.055 Uiso 1 1 calc GR . . . .
H29B H 0.9873 0.3330 0.6319 0.055 Uiso 1 1 calc GR . . . .
H29C H 0.9190 0.3986 0.6494 0.055 Uiso 1 1 calc GR . . . .
C30 C 0.95026(14) 0.3967(2) 0.4490(2) 0.0339(6) Uani 1 1 d . . . . .
H30A H 0.9014 0.3913 0.4543 0.051 Uiso 1 1 calc GR . . . .
H30B H 0.9699 0.3236 0.4519 0.051 Uiso 1 1 calc GR . . . .
H30C H 0.9622 0.4312 0.3853 0.051 Uiso 1 1 calc GR . . . .


_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 1.732(2) . ?
S1 C3 1.730(2) . ?
S2 C10 1.726(2) . ?
S2 C11 1.733(2) . ?
Si1 C1 1.894(2) . ?
Si1 C13 1.888(3) . ?
Si1 C16 1.882(2) . ?
Si1 C19 1.895(2) . ?
Si2 C11 1.894(2) . ?
Si2 C22 1.889(3) . ?
Si2 C25 1.890(2) . ?
Si2 C28 1.887(2) . ?
F1 C5 1.341(3) . ?
F2 C6 1.343(3) . ?
F3 C8 1.343(3) . ?
F4 C9 1.345(3) . ?
N1 C1 1.315(3) . ?
N1 C2 1.369(3) . ?
N2 C11 1.318(3) . ?
N2 C12 1.368(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.368(4) . ?
C3 C4 1.465(3) . ?
C4 C5 1.395(3) . ?
C4 C9 1.399(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.398(3) . ?
C7 C10 1.470(3) . ?
C8 C9 1.374(3) . ?
C10 C12 1.368(4) . ?
C12 H12 0.9500 . ?
C13 H13 1.0000 . ?
C13 C14 1.540(4) . ?
C13 C15 1.532(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.532(3) . ?
C16 C18 1.531(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 1.0000 . ?
C19 C20 1.533(4) . ?
C19 C21 1.535(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 1.0000 . ?
C22 C23 1.535(3) . ?
C22 C24 1.536(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25 1.0000 . ?
C25 C26 1.530(4) . ?
C25 C27 1.543(3) . ?
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 H28 1.0000 . ?
C28 C29 1.540(4) . ?
C28 C30 1.532(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
C3 S1 C1 90.63(12) . . ?
C10 S2 C11 90.55(12) . . ?
C1 Si1 C19 107.08(10) . . ?
C13 Si1 C1 105.56(11) . . ?
C13 Si1 C19 109.83(12) . . ?
C16 Si1 C1 106.76(11) . . ?
C16 Si1 C13 117.22(11) . . ?
C16 Si1 C19 109.82(11) . . ?
C22 Si2 C11 107.83(11) . . ?
C22 Si2 C25 116.85(11) . . ?
C25 Si2 C11 105.28(11) . . ?
C28 Si2 C11 106.81(10) . . ?
C28 Si2 C22 109.59(11) . . ?
C28 Si2 C25 109.93(11) . . ?
C1 N1 C2 111.4(2) . . ?
C11 N2 C12 111.8(2) . . ?
S1 C1 Si1 121.74(14) . . ?
N1 C1 S1 113.22(17) . . ?
N1 C1 Si1 124.97(18) . . ?
N1 C2 H2 121.7 . . ?
C3 C2 N1 116.7(2) . . ?
C3 C2 H2 121.7 . . ?
C2 C3 S1 108.11(17) . . ?
C2 C3 C4 129.2(2) . . ?
C4 C3 S1 122.48(19) . . ?
C5 C4 C3 122.9(2) . . ?
C5 C4 C9 114.4(2) . . ?
C9 C4 C3 122.7(2) . . ?
F1 C5 C4 120.0(2) . . ?
F1 C5 C6 117.4(2) . . ?
C6 C5 C4 122.5(2) . . ?
F2 C6 C5 117.3(2) . . ?
F2 C6 C7 119.9(2) . . ?
C5 C6 C7 122.8(2) . . ?
C6 C7 C8 114.7(2) . . ?
C6 C7 C10 123.8(2) . . ?
C8 C7 C10 121.4(2) . . ?
F3 C8 C7 120.3(2) . . ?
F3 C8 C9 117.1(2) . . ?
C9 C8 C7 122.5(2) . . ?
F4 C9 C4 119.6(2) . . ?
F4 C9 C8 117.4(2) . . ?
C8 C9 C4 123.0(2) . . ?
C7 C10 S2 123.43(19) . . ?
C12 C10 S2 108.72(18) . . ?
C12 C10 C7 127.8(2) . . ?
S2 C11 Si2 123.37(14) . . ?
N2 C11 S2 112.93(17) . . ?
N2 C11 Si2 123.57(18) . . ?
N2 C12 H12 122.0 . . ?
C10 C12 N2 116.0(2) . . ?
C10 C12 H12 122.0 . . ?
Si1 C13 H13 106.5 . . ?
C14 C13 Si1 112.28(19) . . ?
C14 C13 H13 106.5 . . ?
C15 C13 Si1 113.83(18) . . ?
C15 C13 H13 106.5 . . ?
C15 C13 C14 110.8(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C16 H16 105.8 . . ?
C17 C16 Si1 116.00(18) . . ?
C17 C16 H16 105.8 . . ?
C18 C16 Si1 112.17(17) . . ?
C18 C16 H16 105.8 . . ?
C18 C16 C17 110.4(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C19 H19 107.4 . . ?
C20 C19 Si1 112.00(18) . . ?
C20 C19 H19 107.4 . . ?
C20 C19 C21 110.1(2) . . ?
C21 C19 Si1 112.22(18) . . ?
C21 C19 H19 107.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si2 C22 H22 106.6 . . ?
C23 C22 Si2 114.81(17) . . ?
C23 C22 H22 106.6 . . ?
C23 C22 C24 110.3(2) . . ?
C24 C22 Si2 111.43(18) . . ?
C24 C22 H22 106.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Si2 C25 H25 105.8 . . ?
C26 C25 Si2 113.65(17) . . ?
C26 C25 H25 105.8 . . ?
C26 C25 C27 110.9(2) . . ?
C27 C25 Si2 113.99(17) . . ?
C27 C25 H25 105.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
Si2 C28 H28 106.9 . . ?
C29 C28 Si2 112.13(19) . . ?
C29 C28 H28 106.9 . . ?
C30 C28 Si2 113.18(18) . . ?
C30 C28 H28 106.9 . . ?
C30 C28 C29 110.4(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C3 C4 C5 -153.38(19) . . . . ?
S1 C3 C4 C9 23.8(3) . . . . ?
S2 C10 C12 N2 -0.4(3) . . . . ?
F1 C5 C6 F2 -0.5(3) . . . . ?
F1 C5 C6 C7 178.5(2) . . . . ?
F2 C6 C7 C8 -179.6(2) . . . . ?
F2 C6 C7 C10 -1.3(3) . . . . ?
F3 C8 C9 F4 0.7(3) . . . . ?
F3 C8 C9 C4 -178.8(2) . . . . ?
N1 C2 C3 S1 0.2(3) . . . . ?
N1 C2 C3 C4 -174.6(2) . . . . ?
C1 S1 C3 C2 -0.76(18) . . . . ?
C1 S1 C3 C4 174.4(2) . . . . ?
C1 Si1 C13 C14 -65.7(2) . . . . ?
C1 Si1 C13 C15 167.34(19) . . . . ?
C1 Si1 C16 C17 46.9(2) . . . . ?
C1 Si1 C16 C18 174.96(18) . . . . ?
C1 Si1 C19 C20 60.1(2) . . . . ?
C1 Si1 C19 C21 -64.4(2) . . . . ?
C1 N1 C2 C3 0.8(3) . . . . ?
C2 N1 C1 S1 -1.4(3) . . . . ?
C2 N1 C1 Si1 175.67(17) . . . . ?
C2 C3 C4 C5 20.7(4) . . . . ?
C2 C3 C4 C9 -162.1(2) . . . . ?
C3 S1 C1 Si1 -175.90(15) . . . . ?
C3 S1 C1 N1 1.27(19) . . . . ?
C3 C4 C5 F1 -2.7(3) . . . . ?
C3 C4 C5 C6 175.6(2) . . . . ?
C3 C4 C9 F4 5.0(3) . . . . ?
C3 C4 C9 C8 -175.4(2) . . . . ?
C4 C5 C6 F2 -178.9(2) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C4 C9 F4 -177.6(2) . . . . ?
C5 C4 C9 C8 1.9(3) . . . . ?
C5 C6 C7 C8 1.5(3) . . . . ?
C5 C6 C7 C10 179.8(2) . . . . ?
C6 C7 C8 F3 177.0(2) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
C6 C7 C10 S2 -27.6(3) . . . . ?
C6 C7 C10 C12 156.4(2) . . . . ?
C7 C8 C9 F4 179.1(2) . . . . ?
C7 C8 C9 C4 -0.4(4) . . . . ?
C7 C10 C12 N2 176.0(2) . . . . ?
C8 C7 C10 S2 150.54(19) . . . . ?
C8 C7 C10 C12 -25.4(4) . . . . ?
C9 C4 C5 F1 179.91(19) . . . . ?
C9 C4 C5 C6 -1.8(3) . . . . ?
C10 S2 C11 Si2 174.74(15) . . . . ?
C10 S2 C11 N2 -1.23(19) . . . . ?
C10 C7 C8 F3 -1.3(3) . . . . ?
C10 C7 C8 C9 -179.7(2) . . . . ?
C11 S2 C10 C7 -175.7(2) . . . . ?
C11 S2 C10 C12 0.91(18) . . . . ?
C11 Si2 C22 C23 53.5(2) . . . . ?
C11 Si2 C22 C24 179.71(18) . . . . ?
C11 Si2 C25 C26 -65.8(2) . . . . ?
C11 Si2 C25 C27 165.85(18) . . . . ?
C11 Si2 C28 C29 -62.3(2) . . . . ?
C11 Si2 C28 C30 63.3(2) . . . . ?
C11 N2 C12 C10 -0.5(3) . . . . ?
C12 N2 C11 S2 1.2(3) . . . . ?
C12 N2 C11 Si2 -174.77(17) . . . . ?
C13 Si1 C1 S1 -26.24(17) . . . . ?
C13 Si1 C1 N1 156.9(2) . . . . ?
C13 Si1 C16 C17 -71.2(2) . . . . ?
C13 Si1 C16 C18 56.9(2) . . . . ?
C13 Si1 C19 C20 174.22(17) . . . . ?
C13 Si1 C19 C21 49.8(2) . . . . ?
C16 Si1 C1 S1 -151.68(14) . . . . ?
C16 Si1 C1 N1 31.5(2) . . . . ?
C16 Si1 C13 C14 52.9(2) . . . . ?
C16 Si1 C13 C15 -74.0(2) . . . . ?
C16 Si1 C19 C20 -55.5(2) . . . . ?
C16 Si1 C19 C21 -179.94(18) . . . . ?
C19 Si1 C1 S1 90.75(16) . . . . ?
C19 Si1 C1 N1 -86.1(2) . . . . ?
C19 Si1 C13 C14 179.15(18) . . . . ?
C19 Si1 C13 C15 52.2(2) . . . . ?
C19 Si1 C16 C17 162.61(19) . . . . ?
C19 Si1 C16 C18 -69.3(2) . . . . ?
C22 Si2 C11 S2 36.01(18) . . . . ?
C22 Si2 C11 N2 -148.5(2) . . . . ?
C22 Si2 C25 C26 53.8(2) . . . . ?
C22 Si2 C25 C27 -74.5(2) . . . . ?
C22 Si2 C28 C29 -178.85(18) . . . . ?
C22 Si2 C28 C30 -53.2(2) . . . . ?
C25 Si2 C11 S2 161.44(15) . . . . ?
C25 Si2 C11 N2 -23.0(2) . . . . ?
C25 Si2 C22 C23 -64.8(2) . . . . ?
C25 Si2 C22 C24 61.5(2) . . . . ?
C25 Si2 C28 C29 51.4(2) . . . . ?
C25 Si2 C28 C30 177.07(19) . . . . ?
C28 Si2 C11 S2 -81.71(17) . . . . ?
C28 Si2 C11 N2 93.8(2) . . . . ?
C28 Si2 C22 C23 169.36(17) . . . . ?
C28 Si2 C22 C24 -64.4(2) . . . . ?
C28 Si2 C25 C26 179.53(18) . . . . ?
C28 Si2 C25 C27 51.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2f
_database_code_depnum_ccdc_archive 'CCDC 1856901'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2018-02-26
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 F2 N2 S2'
_chemical_formula_sum            'C12 H6 F2 N2 S2'
_chemical_formula_weight         280.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.6214(4)
_cell_length_b                   25.6046(15)
_cell_length_c                   7.2049(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.456(4)
_cell_angle_gamma                90
_cell_volume                     1093.59(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9485
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      62.431
_cell_measurement_theta_min      3.453
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.490
_exptl_absorpt_coefficient_mu    4.523
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.5363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1272 before and 0.0857 after correction. The Ratio of minimum to maximum transmission is 0.7130. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16240
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        62.519
_diffrn_reflns_theta_max         62.519
_diffrn_reflns_theta_min         3.452
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1563
_reflns_number_total             1694
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.244
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.244
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+5.3365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1468
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.3380(2) 0.83303(4) 0.73539(18) 0.0245(4) Uani 1 1 d . . . . .
S2 S 0.6711(2) 0.52078(4) 0.77759(18) 0.0253(4) Uani 1 1 d . . . . .
F1 F 0.1742(5) 0.73569(11) 0.7614(5) 0.0321(7) Uani 1 1 d . . . . .
F2 F 0.7901(5) 0.61723(11) 0.6534(5) 0.0301(7) Uani 1 1 d . . . . .
N1 N 0.6645(8) 0.87067(16) 0.6792(6) 0.0277(10) Uani 1 1 d . . . . .
N2 N 0.2866(8) 0.48274(15) 0.7135(6) 0.0262(10) Uani 1 1 d . . . . .
C1 C 0.5205(8) 0.78908(18) 0.7036(7) 0.0196(10) Uani 1 1 d . . . . .
C2 C 0.6808(9) 0.81761(18) 0.6772(7) 0.0222(11) Uani 1 1 d . . . . .
H2 H 0.798607 0.801070 0.658131 0.027 Uiso 1 1 calc R . . . .
C3 C 0.4904(9) 0.88389(19) 0.7077(7) 0.0276(12) Uani 1 1 d . . . . .
H3 H 0.450669 0.919328 0.712694 0.033 Uiso 1 1 calc R . . . .
C4 C 0.5015(8) 0.73229(18) 0.7071(7) 0.0184(10) Uani 1 1 d . . . . .
C5 C 0.3318(9) 0.70626(18) 0.7353(7) 0.0218(11) Uani 1 1 d . . . . .
C6 C 0.3133(9) 0.65322(18) 0.7418(7) 0.0203(10) Uani 1 1 d . . . . .
H6 H 0.195244 0.638306 0.765098 0.024 Uiso 1 1 calc R . . . .
C7 C 0.4684(8) 0.62076(18) 0.7141(7) 0.0203(10) Uani 1 1 d . . . . .
C8 C 0.6360(8) 0.64641(18) 0.6830(7) 0.0199(10) Uani 1 1 d . . . . .
C9 C 0.6558(9) 0.69974(18) 0.6782(7) 0.0200(10) Uani 1 1 d . . . . .
H9 H 0.774196 0.714633 0.655245 0.024 Uiso 1 1 calc R . . . .
C10 C 0.4491(9) 0.56366(18) 0.7194(7) 0.0219(11) Uani 1 1 d . . . . .
C11 C 0.2608(9) 0.53552(18) 0.6904(7) 0.0235(11) Uani 1 1 d . . . . .
H11 H 0.119942 0.551965 0.656001 0.028 Uiso 1 1 calc R . . . .
C12 C 0.4934(10) 0.47000(19) 0.7601(7) 0.0286(12) Uani 1 1 d . . . . .
H12 H 0.543564 0.434769 0.783167 0.034 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 1.739(5) . ?
S1 C3 1.713(5) . ?
S2 C10 1.730(5) . ?
S2 C12 1.720(5) . ?
F1 C5 1.366(6) . ?
F2 C8 1.356(5) . ?
N1 C2 1.363(6) . ?
N1 C3 1.302(7) . ?
N2 C11 1.363(6) . ?
N2 C12 1.298(7) . ?
C1 C2 1.370(7) . ?
C1 C4 1.461(7) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.397(7) . ?
C4 C9 1.404(7) . ?
C5 C6 1.366(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.403(7) . ?
C7 C8 1.391(7) . ?
C7 C10 1.470(7) . ?
C8 C9 1.374(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(7) . ?
C11 H11 0.9500 . ?
C12 H12 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
C3 S1 C1 89.8(2) . . ?
C12 S2 C10 89.0(3) . . ?
C3 N1 C2 109.9(4) . . ?
C12 N2 C11 110.0(4) . . ?
C2 C1 S1 107.5(3) . . ?
C2 C1 C4 127.7(4) . . ?
C4 C1 S1 124.9(4) . . ?
N1 C2 C1 117.4(5) . . ?
N1 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
S1 C3 H3 122.3 . . ?
N1 C3 S1 115.4(4) . . ?
N1 C3 H3 122.3 . . ?
C5 C4 C1 123.9(4) . . ?
C5 C4 C9 115.1(4) . . ?
C9 C4 C1 121.0(4) . . ?
F1 C5 C4 118.0(4) . . ?
C6 C5 F1 117.3(4) . . ?
C6 C5 C4 124.7(4) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.1(5) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C10 120.5(4) . . ?
C8 C7 C6 115.5(4) . . ?
C8 C7 C10 124.0(4) . . ?
F2 C8 C7 118.4(4) . . ?
F2 C8 C9 117.2(4) . . ?
C9 C8 C7 124.5(4) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.1(4) . . ?
C8 C9 H9 119.9 . . ?
C7 C10 S2 124.3(4) . . ?
C11 C10 S2 108.7(4) . . ?
C11 C10 C7 127.0(5) . . ?
N2 C11 C10 116.5(5) . . ?
N2 C11 H11 121.8 . . ?
C10 C11 H11 121.8 . . ?
S2 C12 H12 122.0 . . ?
N2 C12 S2 115.9(4) . . ?
N2 C12 H12 122.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 N1 -0.5(5) . . . . ?
S1 C1 C4 C5 0.4(6) . . . . ?
S1 C1 C4 C9 179.4(3) . . . . ?
S2 C10 C11 N2 0.4(5) . . . . ?
F1 C5 C6 C7 179.4(4) . . . . ?
F2 C8 C9 C4 179.8(4) . . . . ?
C1 S1 C3 N1 -0.6(4) . . . . ?
C1 C4 C5 F1 -0.1(6) . . . . ?
C1 C4 C5 C6 -179.1(4) . . . . ?
C1 C4 C9 C8 179.7(4) . . . . ?
C2 N1 C3 S1 0.5(5) . . . . ?
C2 C1 C4 C5 179.9(5) . . . . ?
C2 C1 C4 C9 -1.1(7) . . . . ?
C3 S1 C1 C2 0.6(4) . . . . ?
C3 S1 C1 C4 -179.8(4) . . . . ?
C3 N1 C2 C1 0.0(6) . . . . ?
C4 C1 C2 N1 179.9(4) . . . . ?
C4 C5 C6 C7 -1.6(7) . . . . ?
C5 C4 C9 C8 -1.3(6) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C5 C6 C7 C10 -179.6(4) . . . . ?
C6 C7 C8 F2 -179.4(4) . . . . ?
C6 C7 C8 C9 -0.1(7) . . . . ?
C6 C7 C10 S2 -156.4(4) . . . . ?
C6 C7 C10 C11 20.2(7) . . . . ?
C7 C8 C9 C4 0.5(7) . . . . ?
C7 C10 C11 N2 -176.6(4) . . . . ?
C8 C7 C10 S2 23.4(6) . . . . ?
C8 C7 C10 C11 -160.1(5) . . . . ?
C9 C4 C5 F1 -179.1(4) . . . . ?
C9 C4 C5 C6 1.9(7) . . . . ?
C10 S2 C12 N2 0.6(4) . . . . ?
C10 C7 C8 F2 0.8(7) . . . . ?
C10 C7 C8 C9 -179.9(4) . . . . ?
C11 N2 C12 S2 -0.4(5) . . . . ?
C12 S2 C10 C7 176.6(4) . . . . ?
C12 S2 C10 C11 -0.5(4) . . . . ?
C12 N2 C11 C10 0.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4f_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1856902'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_audit_creation_date             2018-02-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H4 F4 N2 S2'
_chemical_formula_sum            'C12 H4 F4 N2 S2'
_chemical_formula_weight         316.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   3.8531(6)
_cell_length_b                   23.868(3)
_cell_length_c                   6.1210(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.290(3)
_cell_angle_gamma                90
_cell_volume                     560.53(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3829
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.493
_cell_measurement_theta_min      3.414
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.653
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1391 before and 0.0648 after correction. The Ratio of minimum to maximum transmission is 0.7358. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.755
_exptl_crystal_size_min          0.066
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7415
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.414
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1184
_reflns_number_total             1261
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²+0.3654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0773
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.49651(10) 0.67209(2) 0.41962(6) 0.01641(14) Uani 1 1 d . . . . .
F1 F 0.2030(2) 0.52835(4) 0.86757(15) 0.0186(2) Uani 1 1 d . . . . .
F2 F 0.2862(2) 0.42307(4) 0.78299(14) 0.0183(2) Uani 1 1 d . . . . .
N1 N 0.2649(4) 0.69927(6) 0.7847(2) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.4032(4) 0.61846(6) 0.5963(2) 0.0135(3) Uani 1 1 d . . . . .
C2 C 0.2833(4) 0.64205(7) 0.7813(3) 0.0174(3) Uani 1 1 d . . . . .
H2 H 0.217360 0.619796 0.899310 0.021 Uiso 1 1 calc R . . . .
C3 C 0.3695(4) 0.71982(7) 0.6045(3) 0.0187(3) Uani 1 1 d . . . . .
H3 H 0.374829 0.758998 0.577587 0.022 Uiso 1 1 calc R . . . .
C4 C 0.4528(4) 0.55917(6) 0.5480(2) 0.0125(3) Uani 1 1 d . . . . .
C5 C 0.3545(4) 0.51615(6) 0.6840(2) 0.0134(3) Uani 1 1 d . . . . .
C6 C 0.3984(4) 0.46017(6) 0.6388(2) 0.0135(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 1.7349(15) . ?
S1 C3 1.7085(16) . ?
F1 C5 1.3451(17) . ?
F2 C6 1.3493(16) . ?
N1 C2 1.368(2) . ?
N1 C3 1.305(2) . ?
C1 C2 1.381(2) . ?
C1 C4 1.462(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.396(2) . ?
C4 C6 1.404(2) 3_666 ?
C5 C6 1.378(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C1 89.47(8) . . ?
C3 N1 C2 109.98(13) . . ?
C2 C1 S1 108.32(11) . . ?
C2 C1 C4 128.33(14) . . ?
C4 C1 S1 123.34(11) . . ?
N1 C2 C1 116.19(14) . . ?
N1 C2 H2 121.9 . . ?
C1 C2 H2 121.9 . . ?
S1 C3 H3 122.0 . . ?
N1 C3 S1 116.04(12) . . ?
N1 C3 H3 122.0 . . ?
C5 C4 C1 122.93(13) . . ?
C5 C4 C6 113.42(13) . 3_666 ?
C6 C4 C1 123.65(13) 3_666 . ?
F1 C5 C4 120.10(13) . . ?
F1 C5 C6 116.62(13) . . ?
C6 C5 C4 123.27(14) . . ?
F2 C6 C4 119.77(13) . 3_666 ?
F2 C6 C5 116.91(13) . . ?
C5 C6 C4 123.32(14) . 3_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 N1 0.05(17) . . . . ?
S1 C1 C4 C5 -175.43(11) . . . . ?
S1 C1 C4 C6 4.3(2) . . . 3_666 ?
F1 C5 C6 F2 -0.2(2) . . . . ?
F1 C5 C6 C4 179.01(12) . . . 3_666 ?
C1 S1 C3 N1 0.03(13) . . . . ?
C1 C4 C5 F1 0.8(2) . . . . ?
C1 C4 C5 C6 179.56(14) . . . . ?
C2 N1 C3 S1 -0.01(17) . . . . ?
C2 C1 C4 C5 5.3(2) . . . . ?
C2 C1 C4 C6 -175.00(15) . . . 3_666 ?
C3 S1 C1 C2 -0.05(12) . . . . ?
C3 S1 C1 C4 -179.48(13) . . . . ?
C3 N1 C2 C1 -0.03(19) . . . . ?
C4 C1 C2 N1 179.45(14) . . . . ?
C4 C5 C6 F2 -178.95(12) . . . . ?
C4 C5 C6 C4 0.2(3) . . . 3_666 ?
C6 C4 C5 F1 -178.95(12) 3_666 . . . ?
C6 C4 C5 C6 -0.2(2) 3_666 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_posa
_database_code_depnum_ccdc_archive 'CCDC 1856899'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
# end Validation Reply Form
_audit_creation_date             2018-06-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 N2 S2'
_chemical_formula_sum            'C12 H8 N2 S2'
_chemical_formula_weight         244.32
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   15.9825(7)
_cell_length_b                   9.7302(4)
_cell_length_c                   13.6524(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2123.12(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      65.290
_cell_measurement_theta_min      5.536
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.643
_exptl_absorpt_coefficient_mu    4.284
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0983 before and 0.0489 after correction. The Ratio of minimum to maximum transmission is 0.7862. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10935
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        65.259
_diffrn_reflns_theta_max         65.259
_diffrn_reflns_theta_min         6.234
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                882
_reflns_number_total             904
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         904
_refine_ls_number_restraints     510
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+2.5140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0621
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.50(4)
 0.50(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 N2-C10A \\sim N2A-C10 \\sim N1-C1A \\sim N1A-C1
 with sigma of 0.01
 S2-C10 \\sim S2A-C10A \\sim S1-C1 \\sim S1A-C1A
 with sigma of 0.01
 N1-C2 \\sim N1A-C2A \\sim N2A-C9A \\sim N2-C9
 with sigma of 0.01
 S1-C3 \\sim S1A-C3 \\sim S2-C8 \\sim S2A-C8
 with sigma of 0.01
 C3-C2A \\sim C3-C2 \\sim C9A-C8 \\sim C9-C8
 with sigma of 0.01
 C4-C3 \\sim C8-C7
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01
Uanis(S2) = Uanis(C9)
Uanis(C2) = Uanis(S1)
Uanis(N1) = Uanis(C1)
Uanis(C10) = Uanis(N2)
Uanis(N2A) = Uanis(C10A) = Uanis(C10) = Uanis(N2)
Uanis(S2) = Uanis(C9) = Uanis(C9A) = Uanis(S2A)
Uanis(C1) = Uanis(N1A) = Uanis(N1) = Uanis(C1A)
Uanis(S1) = Uanis(C2A) = Uanis(C2) = Uanis(S1A)
Uanis(C7) = Uanis(C8)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
6. Others
 Fixed Sof: S1(0.25) C1(0.25) H1(0.25) N1A(0.25) C2A(0.25) H2A(0.25) S2(0.25)
 C10(0.25) H10(0.25) N2A(0.25) C9A(0.25) H9A(0.25) C5(0.5) H5(0.5) C6(0.5)
 H6(0.5) C6A(0.5) H6A(0.5) C5A(0.5) H5A(0.5) C2(0.25) H2(0.25) N1(0.25)
 C1A(0.25) H1A(0.25) S1A(0.25) S2A(0.25) C10A(0.25) H10A(0.25) N2(0.25)
 C9(0.25) H9(0.25)
7.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2A(H2A), C10(H10), C9A(H9A), C5(H5), C6(H6), C6A(H6A), C5A(H5A),
 C2(H2), C1A(H1A), C10A(H10A), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.6712(5) 0.8230(8) 0.7792(3) 0.0235(9) Uani 0.25 1 d D U . A -1
C1 C 0.7233(15) 0.775(2) 0.8854(12) 0.0233(11) Uani 0.25 1 d D U . A -1
H1 H 0.704934 0.804974 0.948108 0.028 Uiso 0.25 1 calc R . . A -1
N1A N 0.7880(13) 0.6980(18) 0.8753(11) 0.0233(11) Uani 0.25 1 d D U . A -1
C2A C 0.7997(10) 0.682(2) 0.7776(10) 0.0235(9) Uani 0.25 1 d D U . A -1
H2A H 0.842665 0.622641 0.754341 0.028 Uiso 0.25 1 calc R . . A -1
S2 S 0.8011(7) 0.6134(12) 0.2256(7) 0.0234(6) Uani 0.25 1 d D U . B -1
C10 C 0.772(3) 0.704(4) 0.121(2) 0.0243(10) Uani 0.25 1 d D U . B -1
H10 H 0.790227 0.673351 0.058320 0.029 Uiso 0.25 1 calc R . . B -1
N2A N 0.726(3) 0.812(4) 0.1286(19) 0.0243(10) Uani 0.25 1 d D U . B -1
C9A C 0.7119(12) 0.827(2) 0.2264(12) 0.0234(6) Uani 0.25 1 d D U . B -1
H9A H 0.673312 0.894219 0.248323 0.028 Uiso 0.25 1 calc R . . B -1
C3 C 0.750000 0.750000 0.7130(3) 0.0235(8) Uani 1 2 d DS TU P . .
C4 C 0.750000 0.750000 0.6057(3) 0.0196(8) Uani 1 2 d DS TU P A .
C5 C 0.7857(16) 0.638(2) 0.5487(18) 0.020(2) Uani 0.5 1 d . U . A -3
H5 H 0.810173 0.561722 0.581692 0.024 Uiso 0.5 1 calc R . . A -3
C6 C 0.7848(15) 0.640(3) 0.455(2) 0.020(3) Uani 0.5 1 d . U . A -3
H6 H 0.808404 0.563798 0.421263 0.024 Uiso 0.5 1 calc R . . A -3
C7 C 0.750000 0.750000 0.3990(3) 0.0215(6) Uani 1 2 d DS TU P . .
C6A C 0.7064(15) 0.850(3) 0.449(2) 0.017(2) Uani 0.5 1 d . U . A -3
H6A H 0.676318 0.919031 0.414679 0.021 Uiso 0.5 1 calc R . . A -3
C5A C 0.7076(16) 0.846(2) 0.5575(16) 0.019(2) Uani 0.5 1 d . U . A -3
H5A H 0.677346 0.913248 0.593318 0.023 Uiso 0.5 1 calc R . . A -3
C8 C 0.750000 0.750000 0.2911(3) 0.0215(6) Uani 1 2 d DS TU P B .
C2 C 0.6873(10) 0.7868(17) 0.7748(10) 0.0235(9) Uani 0.25 1 d D U . A -2
H2 H 0.636278 0.821683 0.749085 0.028 Uiso 0.25 1 calc R . . A -2
N1 N 0.6970(9) 0.7740(16) 0.8729(9) 0.0233(11) Uani 0.25 1 d D U . A -2
C1A C 0.7654(10) 0.7076(19) 0.8878(10) 0.0233(11) Uani 0.25 1 d D U . A -2
H1A H 0.786541 0.690039 0.951591 0.028 Uiso 0.25 1 calc R . . A -2
S1A S 0.8163(4) 0.6526(8) 0.7823(4) 0.0235(9) Uani 0.25 1 d D U . A -2
S2A S 0.6903(7) 0.8851(12) 0.2313(6) 0.0234(6) Uani 0.25 1 d D U . B -2
C10A C 0.720(2) 0.818(3) 0.1184(11) 0.0243(10) Uani 0.25 1 d D U . B -2
H10A H 0.706102 0.858194 0.057128 0.029 Uiso 0.25 1 calc R . . B -2
N2 N 0.764(2) 0.707(3) 0.1278(13) 0.0243(10) Uani 0.25 1 d D U . B -2
C9 C 0.7770(13) 0.668(2) 0.2225(11) 0.0234(6) Uani 0.25 1 d D U . B -2
H9 H 0.804343 0.583671 0.237919 0.028 Uiso 0.25 1 calc R . . B -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 C1 1.736(11) . ?
S1 C3 1.705(7) . ?
C1 H1 0.9500 . ?
C1 N1A 1.286(11) . ?
N1A C2A 1.356(12) . ?
C2A H2A 0.9500 . ?
C2A C3 1.361(11) . ?
S2 C10 1.740(14) . ?
S2 C8 1.798(7) . ?
C10 H10 0.9500 . ?
C10 N2A 1.294(11) . ?
N2A C9A 1.361(13) . ?
C9A H9A 0.9500 . ?
C9A C8 1.306(10) . ?
C3 C4 1.464(5) . ?
C3 C2 1.359(11) . ?
C3 S1A 1.708(6) . ?
C4 C5 1.46(2) . ?
C4 C5A 1.33(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.27(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.43(3) . ?
C7 C6A 1.37(3) . ?
C7 C8 1.473(5) . ?
C6A H6A 0.9500 . ?
C6A C5A 1.49(4) . ?
C5A H5A 0.9500 . ?
C8 S2A 1.818(8) . ?
C8 C9 1.306(10) 14_665 ?
C8 C9 1.306(10) . ?
C2 H2 0.9500 . ?
C2 N1 1.353(12) . ?
N1 C1A 1.287(11) . ?
C1A H1A 0.9500 . ?
C1A S1A 1.738(10) . ?
S2A C10A 1.742(14) . ?
C10A H10A 0.9500 . ?
C10A N2 1.293(12) . ?
N2 C9 1.365(13) . ?
C9 H9 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
C3 S1 C1 88.7(9) . . ?
S1 C1 H1 121.5 . . ?
N1A C1 S1 116.9(17) . . ?
N1A C1 H1 121.5 . . ?
C1 N1A C2A 106.6(18) . . ?
N1A C2A H2A 120.0 . . ?
N1A C2A C3 120.0(16) . . ?
C3 C2A H2A 120.0 . . ?
C10 S2 C8 85.1(16) . . ?
S2 C10 H10 120.1 . . ?
N2A C10 S2 120(4) . . ?
N2A C10 H10 120.1 . . ?
C10 N2A C9A 105(4) . . ?
N2A C9A H9A 119.0 . . ?
C8 C9A N2A 122(3) . . ?
C8 C9A H9A 119.0 . . ?
C2A C3 S1 106.9(8) . . ?
C2A C3 C4 130.4(8) . . ?
C4 C3 S1 122.0(2) . . ?
C4 C3 S1A 123.7(2) . . ?
C2 C3 C4 128.4(7) . . ?
C2 C3 S1A 105.0(8) . . ?
C5 C4 C3 122.3(10) . . ?
C5A C4 C3 119.7(10) . . ?
C5A C4 C5 117.5(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121(2) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 118.3 . . ?
C5 C6 C7 123(2) . . ?
C7 C6 H6 118.3 . . ?
C6 C7 C8 122.4(12) . . ?
C6A C7 C6 117.4(4) . . ?
C6A C7 C8 119.6(12) . . ?
C7 C6A H6A 121.0 . . ?
C7 C6A C5A 118(2) . . ?
C5A C6A H6A 121.0 . . ?
C4 C5A C6A 121.3(19) . . ?
C4 C5A H5A 119.3 . . ?
C6A C5A H5A 119.3 . . ?
C9A C8 S2 107.3(10) . . ?
C9A C8 C7 132.5(10) . . ?
C7 C8 S2 119.8(3) . . ?
C7 C8 S2A 116.7(3) . . ?
C9 C8 C7 135.8(9) . . ?
C9 C8 C7 135.8(9) 14_665 . ?
C9 C8 S2A 107.2(10) . . ?
C9 C8 S2A 20.1(9) 14_665 . ?
C9 C8 C9 88.4(18) . 14_665 ?
C3 C2 H2 119.8 . . ?
N1 C2 C3 120.4(13) . . ?
N1 C2 H2 119.8 . . ?
C1A N1 C2 107.5(12) . . ?
N1 C1A H1A 122.5 . . ?
N1 C1A S1A 114.9(10) . . ?
S1A C1A H1A 122.5 . . ?
C3 S1A C1A 89.9(7) . . ?
C10A S2A C8 89.0(7) . . ?
S2A C10A H10A 124.0 . . ?
N2 C10A S2A 111.9(12) . . ?
N2 C10A H10A 124.0 . . ?
C10A N2 C9 114.3(15) . . ?
C8 C9 N2 117.2(15) . . ?
C8 C9 H9 121.4 . . ?
N2 C9 H9 121.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 N1A C2A 3.5(16) . . . . ?
C1 S1 C3 C2A 8.5(15) . . . . ?
C1 S1 C3 C4 -179.8(8) . . . . ?
C1 N1A C2A C3 4(2) . . . . ?
N1A C2A C3 S1 -9(2) . . . . ?
N1A C2A C3 C4 179.9(13) . . . . ?
S2 C10 N2A C9A 0(6) . . . . ?
C10 S2 C8 C9A 8(2) . . . . ?
C10 S2 C8 C7 -178(2) . . . . ?
C10 N2A C9A C8 8(5) . . . . ?
N2A C9A C8 S2 -11(3) . . . . ?
N2A C9A C8 C7 176(2) . . . . ?
C3 S1 C1 N1A -7.4(13) . . . . ?
C3 C4 C5 C6 179.7(15) . . . . ?
C3 C4 C5A C6A 179.7(12) . . . . ?
C3 C2 N1 C1A -9(2) . . . . ?
C4 C3 C2 N1 176.8(10) . . . . ?
C4 C3 S1A C1A -175.3(6) . . . . ?
C4 C5 C6 C7 1(3) . . . . ?
C5 C4 C5A C6A -8(3) . . . . ?
C5 C6 C7 C6A -8(3) . . . . ?
C5 C6 C7 C8 179.7(16) . . . . ?
C6 C7 C6A C5A 8(3) . . . . ?
C7 C6A C5A C4 1(2) . . . . ?
C7 C8 S2A C10A 179.8(16) . . . . ?
C7 C8 C9 N2 -180(2) . . . . ?
C5A C4 C5 C6 8(3) . . . . ?
C8 S2 C10 N2A -5(5) . . . . ?
C8 C7 C6A C5A 179.7(11) . . . . ?
C8 S2A C10A N2 3(5) . . . . ?
C2 C3 S1A C1A -13.1(10) . . . . ?
C2 N1 C1A S1A -3(2) . . . . ?
N1 C1A S1A C3 10.1(15) . . . . ?
S1A C3 C2 N1 15.8(16) . . . . ?
S2A C8 C9 N2 7(3) . . . . ?
S2A C10A N2 C9 0(7) . . . . ?
C10A N2 C9 C8 -5(6) . . . . ?
C9 C8 S2A C10A -6(2) . . . . ?
C9 C8 S2A C10A 16(4) 14_665 . . . ?
C9 C8 C9 N2 0(2) 14_665 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.50(4)
2 0.50(4)

_vrf_PLAT089_posa                
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........ 3.75 Note
RESPONSE: Compound crystallizes in Fdd2 with half molecule in the
asymmetri unit and showing disorder of both (S and C) and (N and C)
sites. To fix the disorder a whole molecule was used with PART -x
with partial occupancies with bond distance and thermal ellipsoids
restraints and constraints, resulting in poor data to parameter
ratio.
;
