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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl_sq
_database_code_depnum_ccdc_archive 'CCDC 1985443'
loop_
_audit_author_name
_audit_author_address
'Yohei Adachi'
;Hiroshima Univerisity
Japan
;
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_audit_creation_date             2020-03-30
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H30 B F2 N2 S2, F6 P'
_chemical_formula_sum            'C27.50 H31 B Cl F8 N2 P S2'
_chemical_formula_weight         682.89
_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'
B B 0.0013 0.0007 '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'
P P 0.1023 0.0942 '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'
Cl Cl 0.1484 0.1585 '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                   15.040(6)
_cell_length_b                   13.437(5)
_cell_length_c                   16.768(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.168(6)
_cell_angle_gamma                90
_cell_volume                     3160(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1635
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      7.09
_shelx_estimated_absorpt_T_max   0.896
_shelx_estimated_absorpt_T_min   0.755
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29129
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.424
_diffrn_reflns_theta_min         3.015
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4982
_reflns_number_total             7123
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_refine_diff_density_max         1.182
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         7123
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0719
_refine_ls_restrained_S_all      1.140
_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)+(0.1171P)²+2.4957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.2323
_refine_special_details          SQUEEZE
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C1(H1), C5(H5), C12(H12), C8(H8)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C20(H20A,
 H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.77605(6) 0.30780(7) 0.23801(5) 0.0407(2) Uani 1 1 d . . . . .
S2 S 0.64192(6) 0.15607(7) -0.08972(5) 0.0391(2) Uani 1 1 d . . . . .
P1 P 0.73549(8) -0.17900(7) -0.11473(7) 0.0471(3) Uani 1 1 d . . . . .
F1 F 0.30293(17) 0.5169(2) 0.07137(17) 0.0630(7) Uani 1 1 d . . . . .
F2 F 0.23381(15) 0.4331(2) -0.08628(17) 0.0647(7) Uani 1 1 d . . . . .
F7 F 0.8183(3) -0.1024(4) -0.0888(2) 0.1315(17) Uani 1 1 d . . . . .
F5 F 0.8015(4) -0.2692(3) -0.1101(3) 0.153(2) Uani 1 1 d . . . . .
F6 F 0.6629(3) -0.0919(3) -0.1304(4) 0.1389(18) Uani 1 1 d . . . . .
F3 F 0.7396(3) -0.1976(3) -0.0221(2) 0.1110(13) Uani 1 1 d . . . . .
F4 F 0.7277(3) -0.1632(3) -0.2122(2) 0.0964(11) Uani 1 1 d . . . . .
F8 F 0.6499(3) -0.2561(3) -0.1484(2) 0.1304(17) Uani 1 1 d . . . . .
N1 N 0.84753(19) 0.1308(2) 0.10315(17) 0.0366(6) Uani 1 1 d . . . . .
N2 N 0.74370(18) 0.04029(19) 0.13564(16) 0.0317(5) Uani 1 1 d . . . . .
C24 C 0.9864(3) 0.2447(4) 0.1543(3) 0.0576(10) Uani 1 1 d . . . . .
H24A H 0.965967 0.265963 0.200884 0.086 Uiso 1 1 calc R U . . .
H24B H 1.020104 0.299545 0.138832 0.086 Uiso 1 1 calc R U . . .
H24C H 1.029196 0.187373 0.172934 0.086 Uiso 1 1 calc R U . . .
C2 C 0.6511(3) 0.4446(2) 0.2062(2) 0.0392(7) Uani 1 1 d . . . . .
H2 H 0.618334 0.503147 0.211579 0.047 Uiso 1 1 calc R U . . .
C15 C 0.7587(2) 0.1313(2) 0.10734(19) 0.0314(6) Uani 1 1 d . . . . .
C11 C 0.5040(2) 0.2790(3) -0.1462(2) 0.0388(7) Uani 1 1 d . . . . .
H11 H 0.452427 0.316560 -0.183953 0.047 Uiso 1 1 calc R U . . .
C19 C 0.6528(2) 0.0023(3) 0.1453(2) 0.0366(7) Uani 1 1 d . . . . .
C10 C 0.5357(2) 0.2865(2) -0.0547(2) 0.0345(7) Uani 1 1 d . . . . .
C14 C 0.6781(2) 0.2993(2) 0.1417(2) 0.0357(7) Uani 1 1 d . . . . .
C17 C 0.8239(2) -0.0195(3) 0.1470(2) 0.0406(8) Uani 1 1 d . . . . .
C1 C 0.7358(3) 0.4171(3) 0.2645(2) 0.0425(8) Uani 1 1 d . . . . .
H1 H 0.769276 0.454240 0.314619 0.051 Uiso 1 1 calc R U . . .
C9 C 0.4816(2) 0.3461(2) -0.0136(2) 0.0334(7) Uani 1 1 d . . . . .
C5 C 0.4534(3) 0.4453(3) 0.0958(2) 0.0417(8) Uani 1 1 d . . . . .
H5 H 0.475765 0.473848 0.151402 0.050 Uiso 1 1 calc R U . . .
C21 C 0.8382(3) -0.1272(3) 0.1725(3) 0.0582(11) Uani 1 1 d . . . . .
H21A H 0.851751 -0.133248 0.234015 0.087 Uiso 1 1 calc R U . . .
H21B H 0.891866 -0.153934 0.159212 0.087 Uiso 1 1 calc R U . . .
H21C H 0.780247 -0.164710 0.140882 0.087 Uiso 1 1 calc R U . . .
C13 C 0.6142(2) 0.2257(2) -0.0140(2) 0.0346(7) Uani 1 1 d . . . . .
C22 C 0.8389(3) 0.3085(3) 0.0465(3) 0.0510(9) Uani 1 1 d . . . . .
H22A H 0.781670 0.292066 -0.002938 0.076 Uiso 1 1 calc R U . . .
H22B H 0.875858 0.359219 0.030077 0.076 Uiso 1 1 calc R U . . .
H22C H 0.820099 0.334113 0.092818 0.076 Uiso 1 1 calc R U . . .
C12 C 0.5549(3) 0.2130(3) -0.1730(2) 0.0437(8) Uani 1 1 d . . . . .
H12 H 0.543693 0.199693 -0.231478 0.052 Uiso 1 1 calc R U . . .
C25 C 0.5861(3) 0.0858(3) 0.1461(3) 0.0454(8) Uani 1 1 d . . . . .
H25A H 0.617397 0.129556 0.194966 0.068 Uiso 1 1 calc R U . . .
H25B H 0.527966 0.058043 0.150864 0.068 Uiso 1 1 calc R U . . .
H25C H 0.569595 0.124033 0.092934 0.068 Uiso 1 1 calc R U . . .
C16 C 0.8880(2) 0.0385(3) 0.1282(2) 0.0445(8) Uani 1 1 d . . . . .
C4 C 0.5173(2) 0.3883(2) 0.0702(2) 0.0345(7) Uani 1 1 d . . . . .
C6 C 0.3612(3) 0.4612(3) 0.0443(3) 0.0464(9) Uani 1 1 d . . . . .
C18 C 0.8992(2) 0.2157(3) 0.0766(2) 0.0440(8) Uani 1 1 d . . . . .
C26 C 0.6039(3) -0.0662(3) 0.0688(2) 0.0475(9) Uani 1 1 d . . . . .
H26A H 0.594885 -0.030183 0.015571 0.071 Uiso 1 1 calc R U . . .
H26B H 0.541819 -0.087157 0.069475 0.071 Uiso 1 1 calc R U . . .
H26C H 0.643869 -0.124853 0.072360 0.071 Uiso 1 1 calc R U . . .
C8 C 0.3845(2) 0.3634(3) -0.0642(2) 0.0414(8) Uani 1 1 d . . . . .
H8 H 0.358952 0.335082 -0.119745 0.050 Uiso 1 1 calc R U . . .
C7 C 0.3275(3) 0.4188(3) -0.0357(3) 0.0474(9) Uani 1 1 d . . . . .
C23 C 0.9237(3) 0.1787(3) -0.0001(3) 0.0557(10) Uani 1 1 d . . . . .
H23A H 0.954130 0.113186 0.013141 0.084 Uiso 1 1 calc R U . . .
H23B H 0.967401 0.225840 -0.011472 0.084 Uiso 1 1 calc R U . . .
H23C H 0.865120 0.173591 -0.050656 0.084 Uiso 1 1 calc R U . . .
C27 C 0.6779(3) -0.0524(4) 0.2314(3) 0.0627(12) Uani 1 1 d . . . . .
H27A H 0.712283 -0.113926 0.230100 0.094 Uiso 1 1 calc R U . . .
H27B H 0.619126 -0.068520 0.241318 0.094 Uiso 1 1 calc R U . . .
H27C H 0.718122 -0.009540 0.277681 0.094 Uiso 1 1 calc R U . . .
C3 C 0.6146(2) 0.3773(2) 0.1351(2) 0.0335(7) Uani 1 1 d . . . . .
C20 C 0.9859(3) 0.0006(4) 0.1359(4) 0.0713(14) Uani 1 1 d . . . . .
H20A H 0.978990 -0.051213 0.092931 0.107 Uiso 1 1 calc R U . . .
H20B H 1.018247 -0.027096 0.193152 0.107 Uiso 1 1 calc R U . . .
H20C H 1.023622 0.055772 0.126492 0.107 Uiso 1 1 calc R U . . .
B1 B 0.6800(3) 0.2187(3) 0.0785(2) 0.0339(7) 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 C14 1.753(3) . ?
S1 C1 1.707(4) . ?
S2 C13 1.744(3) . ?
S2 C12 1.711(4) . ?
P1 F7 1.552(3) . ?
P1 F5 1.550(4) . ?
P1 F6 1.557(4) . ?
P1 F3 1.552(3) . ?
P1 F4 1.610(3) . ?
P1 F8 1.589(4) . ?
F1 C6 1.350(4) . ?
F2 C7 1.371(4) . ?
N1 C15 1.364(4) . ?
N1 C16 1.379(5) . ?
N1 C18 1.533(4) . ?
N2 C15 1.360(4) . ?
N2 C19 1.522(4) . ?
N2 C17 1.403(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 C18 1.528(5) . ?
C2 H2 0.9500 . ?
C2 C1 1.348(5) . ?
C2 C3 1.437(5) . ?
C15 B1 1.612(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.436(5) . ?
C11 C12 1.351(5) . ?
C19 C25 1.508(5) . ?
C19 C26 1.534(5) . ?
C19 C27 1.540(5) . ?
C10 C9 1.477(5) . ?
C10 C13 1.394(5) . ?
C14 C3 1.394(5) . ?
C14 B1 1.522(5) . ?
C17 C21 1.503(5) . ?
C17 C16 1.361(5) . ?
C1 H1 0.9500 . ?
C9 C4 1.429(5) . ?
C9 C8 1.417(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.411(5) . ?
C5 C6 1.360(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C13 B1 1.513(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 C18 1.518(6) . ?
C12 H12 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C16 C20 1.519(5) . ?
C4 C3 1.483(5) . ?
C6 C7 1.374(6) . ?
C18 C23 1.543(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C7 1.347(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C14 92.11(17) . . ?
C12 S2 C13 92.33(17) . . ?
F7 P1 F6 89.5(3) . . ?
F7 P1 F4 87.3(2) . . ?
F7 P1 F8 175.8(2) . . ?
F5 P1 F7 94.0(3) . . ?
F5 P1 F6 173.4(3) . . ?
F5 P1 F3 91.7(2) . . ?
F5 P1 F4 88.0(2) . . ?
F5 P1 F8 86.0(3) . . ?
F6 P1 F4 86.6(2) . . ?
F6 P1 F8 90.0(3) . . ?
F3 P1 F7 95.1(2) . . ?
F3 P1 F6 93.6(3) . . ?
F3 P1 F4 177.6(2) . . ?
F3 P1 F8 89.1(2) . . ?
F8 P1 F4 88.4(2) . . ?
C15 N1 C16 108.7(3) . . ?
C15 N1 C18 128.3(3) . . ?
C16 N1 C18 122.9(3) . . ?
C15 N2 C19 127.4(3) . . ?
C15 N2 C17 108.6(3) . . ?
C17 N2 C19 123.7(3) . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C24 H24A 109.5 . . ?
C18 C24 H24B 109.5 . . ?
C18 C24 H24C 109.5 . . ?
C1 C2 H2 123.0 . . ?
C1 C2 C3 114.0(3) . . ?
C3 C2 H2 123.0 . . ?
N1 C15 B1 128.0(3) . . ?
N2 C15 N1 107.6(3) . . ?
N2 C15 B1 124.3(3) . . ?
C10 C11 H11 123.5 . . ?
C12 C11 H11 123.5 . . ?
C12 C11 C10 113.1(3) . . ?
N2 C19 C26 106.8(3) . . ?
N2 C19 C27 109.6(3) . . ?
C25 C19 N2 112.1(3) . . ?
C25 C19 C26 109.5(3) . . ?
C25 C19 C27 106.6(3) . . ?
C26 C19 C27 112.3(3) . . ?
C11 C10 C9 120.6(3) . . ?
C13 C10 C11 112.2(3) . . ?
C13 C10 C9 127.0(3) . . ?
C3 C14 S1 110.4(2) . . ?
C3 C14 B1 131.6(3) . . ?
B1 C14 S1 117.8(2) . . ?
N2 C17 C21 128.1(3) . . ?
C16 C17 N2 106.7(3) . . ?
C16 C17 C21 125.2(3) . . ?
S1 C1 H1 123.9 . . ?
C2 C1 S1 112.2(3) . . ?
C2 C1 H1 123.9 . . ?
C4 C9 C10 126.8(3) . . ?
C8 C9 C10 115.6(3) . . ?
C8 C9 C4 117.6(3) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C6 C5 C4 122.8(4) . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C13 S2 109.9(2) . . ?
C10 C13 B1 131.5(3) . . ?
B1 C13 S2 118.3(2) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
S2 C12 H12 123.8 . . ?
C11 C12 S2 112.4(3) . . ?
C11 C12 H12 123.8 . . ?
C19 C25 H25A 109.5 . . ?
C19 C25 H25B 109.5 . . ?
C19 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C16 C20 129.4(4) . . ?
C17 C16 N1 108.3(3) . . ?
C17 C16 C20 122.3(4) . . ?
C9 C4 C3 127.0(3) . . ?
C5 C4 C9 117.4(3) . . ?
C5 C4 C3 115.6(3) . . ?
F1 C6 C5 120.6(4) . . ?
F1 C6 C7 120.2(3) . . ?
C5 C6 C7 119.2(3) . . ?
N1 C18 C23 107.5(3) . . ?
C24 C18 N1 108.2(3) . . ?
C24 C18 C23 113.7(3) . . ?
C22 C18 N1 113.8(3) . . ?
C22 C18 C24 107.5(3) . . ?
C22 C18 C23 106.3(3) . . ?
C19 C26 H26A 109.5 . . ?
C19 C26 H26B 109.5 . . ?
C19 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C9 C8 H8 119.0 . . ?
C7 C8 C9 121.9(4) . . ?
C7 C8 H8 119.0 . . ?
F2 C7 C6 118.7(3) . . ?
C8 C7 F2 120.1(4) . . ?
C8 C7 C6 121.2(3) . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C27 H27A 109.5 . . ?
C19 C27 H27B 109.5 . . ?
C19 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C2 C3 C4 121.7(3) . . ?
C14 C3 C2 111.2(3) . . ?
C14 C3 C4 126.8(3) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 B1 C15 120.4(3) . . ?
C13 B1 C15 119.3(3) . . ?
C13 B1 C14 120.0(3) . . ?

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 C14 C3 C2 3.6(3) . . . . ?
S1 C14 C3 C4 -170.2(2) . . . . ?
S1 C14 B1 C15 12.0(4) . . . . ?
S1 C14 B1 C13 -162.0(2) . . . . ?
S2 C13 B1 C15 -13.2(4) . . . . ?
S2 C13 B1 C14 160.9(2) . . . . ?
F1 C6 C7 F2 -0.9(5) . . . . ?
F1 C6 C7 C8 179.7(3) . . . . ?
N1 C15 B1 C14 -89.4(4) . . . . ?
N1 C15 B1 C13 84.7(4) . . . . ?
N2 C15 B1 C14 95.2(4) . . . . ?
N2 C15 B1 C13 -90.7(4) . . . . ?
N2 C17 C16 N1 -1.9(4) . . . . ?
N2 C17 C16 C20 178.0(4) . . . . ?
C15 N1 C16 C17 0.8(4) . . . . ?
C15 N1 C16 C20 -179.0(4) . . . . ?
C15 N1 C18 C24 115.2(4) . . . . ?
C15 N1 C18 C22 -4.1(5) . . . . ?
C15 N1 C18 C23 -121.6(4) . . . . ?
C15 N2 C19 C25 -17.7(4) . . . . ?
C15 N2 C19 C26 102.2(4) . . . . ?
C15 N2 C19 C27 -135.9(3) . . . . ?
C15 N2 C17 C21 -176.2(3) . . . . ?
C15 N2 C17 C16 2.3(4) . . . . ?
C11 C10 C9 C4 -157.3(3) . . . . ?
C11 C10 C9 C8 21.8(4) . . . . ?
C11 C10 C13 S2 -3.4(3) . . . . ?
C11 C10 C13 B1 170.4(3) . . . . ?
C19 N2 C15 N1 -175.7(3) . . . . ?
C19 N2 C15 B1 0.4(5) . . . . ?
C19 N2 C17 C21 -2.0(5) . . . . ?
C19 N2 C17 C16 176.5(3) . . . . ?
C10 C11 C12 S2 0.8(4) . . . . ?
C10 C9 C4 C5 178.2(3) . . . . ?
C10 C9 C4 C3 -3.1(5) . . . . ?
C10 C9 C8 C7 -178.1(3) . . . . ?
C10 C13 B1 C15 173.4(3) . . . . ?
C10 C13 B1 C14 -12.4(5) . . . . ?
C14 S1 C1 C2 2.4(3) . . . . ?
C17 N2 C15 N1 -1.8(3) . . . . ?
C17 N2 C15 B1 174.4(3) . . . . ?
C17 N2 C19 C25 169.2(3) . . . . ?
C17 N2 C19 C26 -70.9(4) . . . . ?
C17 N2 C19 C27 51.0(4) . . . . ?
C1 S1 C14 C3 -3.5(3) . . . . ?
C1 S1 C14 B1 171.1(3) . . . . ?
C1 C2 C3 C14 -1.9(4) . . . . ?
C1 C2 C3 C4 172.3(3) . . . . ?
C9 C10 C13 S2 170.8(3) . . . . ?
C9 C10 C13 B1 -15.4(6) . . . . ?
C9 C4 C3 C2 161.6(3) . . . . ?
C9 C4 C3 C14 -25.2(5) . . . . ?
C9 C8 C7 F2 -179.5(3) . . . . ?
C9 C8 C7 C6 -0.1(5) . . . . ?
C5 C4 C3 C2 -19.7(4) . . . . ?
C5 C4 C3 C14 153.5(3) . . . . ?
C5 C6 C7 F2 178.3(3) . . . . ?
C5 C6 C7 C8 -1.1(6) . . . . ?
C21 C17 C16 N1 176.7(3) . . . . ?
C21 C17 C16 C20 -3.4(6) . . . . ?
C13 S2 C12 C11 -2.4(3) . . . . ?
C13 C10 C9 C4 29.0(5) . . . . ?
C13 C10 C9 C8 -151.9(3) . . . . ?
C12 S2 C13 C10 3.3(3) . . . . ?
C12 S2 C13 B1 -171.4(3) . . . . ?
C12 C11 C10 C9 -172.8(3) . . . . ?
C12 C11 C10 C13 1.8(4) . . . . ?
C16 N1 C15 N2 0.6(3) . . . . ?
C16 N1 C15 B1 -175.4(3) . . . . ?
C16 N1 C18 C24 -64.2(4) . . . . ?
C16 N1 C18 C22 176.5(3) . . . . ?
C16 N1 C18 C23 59.1(4) . . . . ?
C4 C9 C8 C7 1.1(5) . . . . ?
C4 C5 C6 F1 -179.5(3) . . . . ?
C4 C5 C6 C7 1.2(5) . . . . ?
C6 C5 C4 C9 -0.2(5) . . . . ?
C6 C5 C4 C3 -179.0(3) . . . . ?
C18 N1 C15 N2 -178.8(3) . . . . ?
C18 N1 C15 B1 5.2(5) . . . . ?
C18 N1 C16 C17 -179.7(3) . . . . ?
C18 N1 C16 C20 0.5(6) . . . . ?
C8 C9 C4 C5 -0.9(4) . . . . ?
C8 C9 C4 C3 177.8(3) . . . . ?
C3 C2 C1 S1 -0.8(4) . . . . ?
C3 C14 B1 C15 -174.7(3) . . . . ?
C3 C14 B1 C13 11.2(5) . . . . ?
B1 C14 C3 C2 -170.0(3) . . . . ?
B1 C14 C3 C4 16.2(5) . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 198 62 ' '
2 1.000 0.500 1.000 198 62 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
