# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_20180614b
_database_code_depnum_ccdc_archive 'CCDC 1871714'
_audit_update_record             
;
2018-10-06 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;
_audit_creation_date             2018-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H29 B F2 N2 S2'
_chemical_formula_sum            'C32 H29 B F2 N2 S2'
_chemical_formula_weight         554.50
_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'
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                   7.8488(3)
_cell_length_b                   12.9762(5)
_cell_length_c                   17.3391(7)
_cell_angle_alpha                102.951(2)
_cell_angle_beta                 90.009(2)
_cell_angle_gamma                98.8670(10)
_cell_volume                     1699.35(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.549
_cell_measurement_theta_min      3.001
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            86806
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         3.617
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5482
_reflns_number_total             7539
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         7539
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+0.5761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1395
_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
 Sof(S1A)=Sof(S2A)=Sof(F1A)=Sof(F2A)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-
 FVAR(1)
 Sof(S1)=Sof(S2)=Sof(F1)=Sof(F2)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15),
 C19(H19), C21(H21), C27(H27), C28(H28), C30(H30), C31(H31)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C32(H32A,H32B,
 H32C), C23(H23A,H23B,H23C), C23A(H23D,H23E,H23F)
;
_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
N1 N 0.55705(18) 0.79126(10) 0.15470(8) 0.0492(3) Uani 1 1 d . . . . .
N2 N 0.81237(19) 0.84770(10) 0.24704(8) 0.0503(3) Uani 1 1 d . . . . .
C1 C 0.4316(2) 0.79135(13) 0.10199(11) 0.0564(4) Uani 1 1 d . . . . .
C2 C 0.3659(3) 0.68490(15) 0.06278(13) 0.0673(5) Uani 1 1 d . . . . .
H2 H 0.279963 0.663362 0.022946 0.081 Uiso 1 1 calc R . . . .
C3 C 0.4525(2) 0.61950(14) 0.09450(12) 0.0617(5) Uani 1 1 d . . . . .
H3 H 0.434906 0.545058 0.080411 0.074 Uiso 1 1 calc R . . . .
C4 C 0.5729(2) 0.68464(12) 0.15224(11) 0.0504(4) Uani 1 1 d . . . . .
C5 C 0.6966(2) 0.65932(12) 0.19910(10) 0.0487(4) Uani 1 1 d . . . . .
C6 C 0.8182(2) 0.73969(12) 0.24405(10) 0.0510(4) Uani 1 1 d . . . . .
C7 C 0.9646(3) 0.73475(14) 0.28880(12) 0.0648(5) Uani 1 1 d . . . . .
H7 H 0.999297 0.672830 0.297564 0.078 Uiso 1 1 calc R . . . .
C8 C 1.0473(3) 0.83732(15) 0.31724(14) 0.0726(6) Uani 1 1 d . . . . .
H8 H 1.149440 0.857715 0.347774 0.087 Uiso 1 1 calc R . . . .
C9 C 0.9488(3) 0.90621(14) 0.29163(12) 0.0598(5) Uani 1 1 d . . . . .
C10 C 0.1798(2) 0.86979(14) 0.03346(12) 0.0568(4) Uani 1 1 d . . . . .
C11 C 0.1661(3) 0.90426(15) -0.03536(12) 0.0603(5) Uani 1 1 d . . . . .
H11 H 0.260934 0.944082 -0.052859 0.072 Uiso 1 1 calc R . . . .
C12 C 0.0120(3) 0.87983(16) -0.07838(13) 0.0666(5) Uani 1 1 d . . . . .
H12 H 0.003519 0.905149 -0.124117 0.080 Uiso 1 1 calc R . . . .
C13 C -0.1294(3) 0.81897(17) -0.05540(14) 0.0695(5) Uani 1 1 d . . . . .
C14 C -0.1138(3) 0.78481(19) 0.01389(15) 0.0772(6) Uani 1 1 d . . . . .
H14 H -0.207856 0.743142 0.030313 0.093 Uiso 1 1 calc R . . . .
C15 C 0.0369(3) 0.81073(18) 0.05916(14) 0.0714(5) Uani 1 1 d . . . . .
H15 H 0.043256 0.788975 0.106523 0.086 Uiso 1 1 calc R . . . .
C16 C -0.2976(4) 0.7915(3) -0.1034(2) 0.1156(10) Uani 1 1 d . . . . .
H16A H -0.385246 0.823670 -0.072641 0.173 Uiso 1 1 calc GR . . . .
H16B H -0.331308 0.715120 -0.117280 0.173 Uiso 1 1 calc GR . . . .
H16C H -0.282939 0.818112 -0.150728 0.173 Uiso 1 1 calc GR . . . .
C17 C 0.6951(2) 0.54569(12) 0.20477(10) 0.0503(4) Uani 1 1 d . . . . .
C18 C 0.5779(3) 0.50418(16) 0.25470(14) 0.0737(6) Uani 1 1 d . . . . .
C19 C 0.5804(3) 0.40021(16) 0.26311(14) 0.0797(7) Uani 1 1 d . . . . .
H19 H 0.503291 0.372445 0.296799 0.096 Uiso 1 1 calc R . . . .
C20 C 0.6919(3) 0.33745(14) 0.22378(12) 0.0659(5) Uani 1 1 d . . . . .
C21 C 0.8038(3) 0.37986(14) 0.17343(12) 0.0620(5) Uani 1 1 d . . . . .
H21 H 0.879293 0.337768 0.145546 0.074 Uiso 1 1 calc R . . . .
C22 C 0.8076(2) 0.48306(13) 0.16292(10) 0.0520(4) Uani 1 1 d . . . . .
C24 C 0.6900(4) 0.22514(18) 0.23496(18) 0.0998(9) Uani 1 1 d . . . . .
H24A H 0.655425 0.174600 0.185925 0.150 Uiso 1 1 calc GR . . . .
H24B H 0.609907 0.212007 0.274826 0.150 Uiso 1 1 calc GR . . . .
H24C H 0.803345 0.217426 0.251232 0.150 Uiso 1 1 calc GR . . . .
C25 C 0.9322(3) 0.52441(17) 0.10703(15) 0.0816(7) Uani 1 1 d . . . . .
H25A H 0.871370 0.553677 0.071109 0.122 Uiso 1 1 calc GR . . . .
H25B H 0.985663 0.466780 0.077603 0.122 Uiso 1 1 calc GR . . . .
H25C H 1.019128 0.579220 0.136625 0.122 Uiso 1 1 calc GR . . . .
C26 C 1.1588(3) 1.07793(14) 0.37944(13) 0.0622(5) Uani 1 1 d . . . . .
C27 C 1.1362(3) 1.10298(19) 0.46047(15) 0.0797(6) Uani 1 1 d . . . . .
H27 H 1.025310 1.100616 0.479653 0.096 Uiso 1 1 calc R . . . .
C28 C 1.2765(3) 1.1313(2) 0.51267(13) 0.0795(6) Uani 1 1 d . . . . .
H28 H 1.258973 1.147134 0.566823 0.095 Uiso 1 1 calc R . . . .
C29 C 1.4414(3) 1.13654(15) 0.48637(12) 0.0646(5) Uani 1 1 d . . . . .
C30 C 1.4625(3) 1.11118(17) 0.40633(13) 0.0700(5) Uani 1 1 d . . . . .
H30 H 1.573585 1.113131 0.387438 0.084 Uiso 1 1 calc R . . . .
C31 C 1.3243(3) 1.08290(17) 0.35307(12) 0.0692(5) Uani 1 1 d . . . . .
H31 H 1.342796 1.067080 0.299015 0.083 Uiso 1 1 calc R . . . .
C32 C 1.5953(4) 1.1650(2) 0.54371(16) 0.0945(8) Uani 1 1 d . . . . .
H32A H 1.655172 1.234866 0.542336 0.142 Uiso 1 1 calc GR . . . .
H32B H 1.671630 1.113304 0.528969 0.142 Uiso 1 1 calc GR . . . .
H32C H 1.556880 1.164941 0.596265 0.142 Uiso 1 1 calc GR . . . .
B1 B 0.6571(3) 0.88832(15) 0.21484(14) 0.0588(5) Uani 1 1 d . . . . .
S1 S 0.3722(5) 0.9136(3) 0.0943(3) 0.0713(8) Uani 0.63(3) 1 d . . P A 1
S2 S 0.9752(5) 1.0450(2) 0.3150(3) 0.0736(9) Uani 0.63(3) 1 d . . P A 1
F1 F 0.544(2) 0.9128(14) 0.2794(8) 0.095(3) Uani 0.63(3) 1 d . . P A 1
F2 F 0.7029(15) 0.9729(7) 0.1866(8) 0.087(3) Uani 0.63(3) 1 d . . P A 1
C23 C 0.473(2) 0.5815(11) 0.3083(11) 0.147(6) Uani 0.63(3) 1 d . . P A 1
H23A H 0.546948 0.647899 0.330068 0.220 Uiso 0.63(3) 1 calc GR . P A 1
H23B H 0.426804 0.550075 0.350449 0.220 Uiso 0.63(3) 1 calc GR . P A 1
H23C H 0.380265 0.594605 0.277544 0.220 Uiso 0.63(3) 1 calc GR . P A 1
S1A S 0.3804(10) 0.9077(6) 0.0837(8) 0.088(2) Uani 0.37(3) 1 d . . P A 2
S2A S 0.9900(12) 1.0453(5) 0.3043(7) 0.102(2) Uani 0.37(3) 1 d . . P A 2
F1A F 0.572(3) 0.934(2) 0.2693(15) 0.098(6) Uani 0.37(3) 1 d . . P A 2
F2A F 0.730(2) 0.9629(14) 0.1661(10) 0.078(3) Uani 0.37(3) 1 d . . P A 2
C23A C 0.428(2) 0.5559(13) 0.2918(13) 0.088(4) Uani 0.37(3) 1 d . . P A 2
H23D H 0.461550 0.632232 0.306421 0.133 Uiso 0.37(3) 1 calc GR . P A 2
H23E H 0.394693 0.529723 0.338057 0.133 Uiso 0.37(3) 1 calc GR . P A 2
H23F H 0.331714 0.538565 0.254319 0.133 Uiso 0.37(3) 1 calc GR . 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
N1 C1 1.344(2) . ?
N1 C4 1.3993(19) . ?
N1 B1 1.548(2) . ?
N2 C6 1.3987(19) . ?
N2 C9 1.344(2) . ?
N2 B1 1.551(2) . ?
C1 C2 1.413(2) . ?
C1 S1 1.754(3) . ?
C1 S1A 1.716(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.409(3) . ?
C4 C5 1.389(2) . ?
C5 C6 1.391(2) . ?
C5 C17 1.498(2) . ?
C6 C7 1.404(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.369(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.409(2) . ?
C9 S2 1.734(3) . ?
C9 S2A 1.748(6) . ?
C10 C11 1.375(3) . ?
C10 C15 1.390(3) . ?
C10 S1 1.784(4) . ?
C10 S1A 1.746(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(3) . ?
C13 C14 1.382(3) . ?
C13 C16 1.511(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.373(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.394(3) . ?
C17 C22 1.387(2) . ?
C18 C19 1.392(3) . ?
C18 C23 1.544(12) . ?
C18 C23A 1.518(17) . ?
C19 H19 0.9300 . ?
C19 C20 1.365(3) . ?
C20 C21 1.379(3) . ?
C20 C24 1.511(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.387(2) . ?
C22 C25 1.502(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.387(3) . ?
C26 C31 1.374(3) . ?
C26 S2 1.761(3) . ?
C26 S2A 1.792(7) . ?
C27 H27 0.9300 . ?
C27 C28 1.376(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.369(3) . ?
C29 C30 1.369(3) . ?
C29 C32 1.511(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.375(3) . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
B1 F1 1.440(17) . ?
B1 F2 1.300(10) . ?
B1 F1A 1.25(3) . ?
B1 F2A 1.474(15) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 107.92(14) . . ?
C1 N1 B1 127.83(14) . . ?
C4 N1 B1 123.99(14) . . ?
C6 N2 B1 123.66(14) . . ?
C9 N2 C6 107.88(14) . . ?
C9 N2 B1 127.78(14) . . ?
N1 C1 C2 109.55(15) . . ?
N1 C1 S1 119.18(18) . . ?
N1 C1 S1A 122.1(3) . . ?
C2 C1 S1 131.24(19) . . ?
C2 C1 S1A 128.1(3) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 C1 107.03(17) . . ?
C3 C2 H2 126.5 . . ?
C2 C3 H3 126.0 . . ?
C2 C3 C4 108.04(16) . . ?
C4 C3 H3 126.0 . . ?
N1 C4 C3 107.45(15) . . ?
C5 C4 N1 121.06(15) . . ?
C5 C4 C3 131.42(15) . . ?
C4 C5 C6 120.38(14) . . ?
C4 C5 C17 120.26(15) . . ?
C6 C5 C17 119.29(15) . . ?
N2 C6 C7 107.61(15) . . ?
C5 C6 N2 121.01(15) . . ?
C5 C6 C7 131.30(15) . . ?
C6 C7 H7 126.1 . . ?
C8 C7 C6 107.84(15) . . ?
C8 C7 H7 126.1 . . ?
C7 C8 H8 126.4 . . ?
C7 C8 C9 107.25(17) . . ?
C9 C8 H8 126.4 . . ?
N2 C9 C8 109.39(16) . . ?
N2 C9 S2 120.99(16) . . ?
N2 C9 S2A 120.7(3) . . ?
C8 C9 S2 129.47(18) . . ?
C8 C9 S2A 129.7(3) . . ?
C11 C10 C15 119.45(18) . . ?
C11 C10 S1 119.7(2) . . ?
C11 C10 S1A 115.8(4) . . ?
C15 C10 S1 120.5(2) . . ?
C15 C10 S1A 124.8(4) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.00(18) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.59(19) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C14 117.8(2) . . ?
C12 C13 C16 121.3(2) . . ?
C14 C13 C16 120.9(2) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.8(2) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 H15 120.3 . . ?
C14 C15 C10 119.3(2) . . ?
C14 C15 H15 120.3 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C5 117.95(15) . . ?
C22 C17 C5 121.75(15) . . ?
C22 C17 C18 120.29(15) . . ?
C17 C18 C23 118.1(5) . . ?
C17 C18 C23A 125.4(6) . . ?
C19 C18 C17 118.44(18) . . ?
C19 C18 C23 122.7(5) . . ?
C19 C18 C23A 115.5(6) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 C18 122.51(19) . . ?
C20 C19 H19 118.7 . . ?
C19 C20 C21 117.74(16) . . ?
C19 C20 C24 120.6(2) . . ?
C21 C20 C24 121.69(19) . . ?
C20 C21 H21 118.8 . . ?
C20 C21 C22 122.32(17) . . ?
C22 C21 H21 118.8 . . ?
C17 C22 C25 121.59(15) . . ?
C21 C22 C17 118.66(16) . . ?
C21 C22 C25 119.75(16) . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 S2 118.8(3) . . ?
C27 C26 S2A 125.7(5) . . ?
C31 C26 C27 118.26(19) . . ?
C31 C26 S2 122.9(3) . . ?
C31 C26 S2A 116.0(5) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.5(2) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 119.4 . . ?
C29 C28 C27 121.2(2) . . ?
C29 C28 H28 119.4 . . ?
C28 C29 C32 121.2(2) . . ?
C30 C29 C28 117.9(2) . . ?
C30 C29 C32 120.8(2) . . ?
C29 C30 H30 119.1 . . ?
C29 C30 C31 121.9(2) . . ?
C31 C30 H30 119.1 . . ?
C26 C31 C30 120.2(2) . . ?
C26 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N1 B1 N2 106.15(13) . . ?
F1 B1 N1 106.0(6) . . ?
F1 B1 N2 107.4(6) . . ?
F2 B1 N1 114.5(5) . . ?
F2 B1 N2 112.9(5) . . ?
F2 B1 F1 109.5(9) . . ?
F1A B1 N1 116.4(12) . . ?
F1A B1 N2 112.1(12) . . ?
F1A B1 F2A 110.7(16) . . ?
F2A B1 N1 104.5(7) . . ?
F2A B1 N2 106.3(7) . . ?
C1 S1 C10 101.6(2) . . ?
C9 S2 C26 101.69(16) . . ?
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 . . ?
C1 S1A C10 104.7(3) . . ?
C9 S2A C26 99.9(3) . . ?
C18 C23A H23D 109.5 . . ?
C18 C23A H23E 109.5 . . ?
C18 C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 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
N1 C1 C2 C3 1.4(2) . . . . ?
N1 C1 S1 C10 -169.0(2) . . . . ?
N1 C1 S1A C10 -164.7(4) . . . . ?
N1 C4 C5 C6 -6.1(3) . . . . ?
N1 C4 C5 C17 170.96(15) . . . . ?
N2 C6 C7 C8 -0.9(2) . . . . ?
N2 C9 S2 C26 175.2(2) . . . . ?
N2 C9 S2A C26 171.0(3) . . . . ?
C1 N1 C4 C3 0.9(2) . . . . ?
C1 N1 C4 C5 178.18(16) . . . . ?
C1 N1 B1 N2 -167.55(16) . . . . ?
C1 N1 B1 F1 78.5(7) . . . . ?
C1 N1 B1 F2 -42.3(7) . . . . ?
C1 N1 B1 F1A 66.9(16) . . . . ?
C1 N1 B1 F2A -55.4(7) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C2 C1 S1 C10 8.6(5) . . . . ?
C2 C1 S1A C10 21.0(9) . . . . ?
C2 C3 C4 N1 0.0(2) . . . . ?
C2 C3 C4 C5 -177.0(2) . . . . ?
C3 C4 C5 C6 170.54(19) . . . . ?
C3 C4 C5 C17 -12.4(3) . . . . ?
C4 N1 C1 C2 -1.4(2) . . . . ?
C4 N1 C1 S1 176.8(2) . . . . ?
C4 N1 C1 S1A -176.6(5) . . . . ?
C4 N1 B1 N2 19.2(2) . . . . ?
C4 N1 B1 F1 -94.8(7) . . . . ?
C4 N1 B1 F2 144.4(7) . . . . ?
C4 N1 B1 F1A -106.3(16) . . . . ?
C4 N1 B1 F2A 131.3(7) . . . . ?
C4 C5 C6 N2 4.0(3) . . . . ?
C4 C5 C6 C7 -172.45(19) . . . . ?
C4 C5 C17 C18 -79.3(2) . . . . ?
C4 C5 C17 C22 101.6(2) . . . . ?
C5 C6 C7 C8 175.9(2) . . . . ?
C5 C17 C18 C19 -177.2(2) . . . . ?
C5 C17 C18 C23 -7.2(10) . . . . ?
C5 C17 C18 C23A 12.7(11) . . . . ?
C5 C17 C22 C21 177.44(17) . . . . ?
C5 C17 C22 C25 -2.6(3) . . . . ?
C6 N2 C9 C8 1.0(2) . . . . ?
C6 N2 C9 S2 -175.0(3) . . . . ?
C6 N2 C9 S2A 176.6(5) . . . . ?
C6 N2 B1 N1 -21.2(2) . . . . ?
C6 N2 B1 F1 91.8(8) . . . . ?
C6 N2 B1 F2 -147.4(7) . . . . ?
C6 N2 B1 F1A 106.9(16) . . . . ?
C6 N2 B1 F2A -132.0(8) . . . . ?
C6 C5 C17 C18 97.8(2) . . . . ?
C6 C5 C17 C22 -81.3(2) . . . . ?
C6 C7 C8 C9 1.5(3) . . . . ?
C7 C8 C9 N2 -1.6(3) . . . . ?
C7 C8 C9 S2 173.9(3) . . . . ?
C7 C8 C9 S2A -176.7(6) . . . . ?
C8 C9 S2 C26 0.1(5) . . . . ?
C8 C9 S2A C26 -14.4(9) . . . . ?
C9 N2 C6 C5 -177.28(17) . . . . ?
C9 N2 C6 C7 -0.1(2) . . . . ?
C9 N2 B1 N1 169.43(17) . . . . ?
C9 N2 B1 F1 -77.5(8) . . . . ?
C9 N2 B1 F2 43.3(8) . . . . ?
C9 N2 B1 F1A -62.5(16) . . . . ?
C9 N2 B1 F2A 58.6(8) . . . . ?
C10 C11 C12 C13 -1.6(3) . . . . ?
C11 C10 C15 C14 2.2(3) . . . . ?
C11 C10 S1 C1 -124.9(2) . . . . ?
C11 C10 S1A C1 -130.2(5) . . . . ?
C11 C12 C13 C14 1.6(3) . . . . ?
C11 C12 C13 C16 -179.3(2) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C10 -2.3(3) . . . . ?
C15 C10 C11 C12 -0.3(3) . . . . ?
C15 C10 S1 C1 62.1(4) . . . . ?
C15 C10 S1A C1 51.3(9) . . . . ?
C16 C13 C14 C15 -178.7(2) . . . . ?
C17 C5 C6 N2 -173.03(15) . . . . ?
C17 C5 C6 C7 10.5(3) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C18 C17 C22 C21 -1.6(3) . . . . ?
C18 C17 C22 C25 178.4(2) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C18 C19 C20 C24 179.9(3) . . . . ?
C19 C20 C21 C22 1.0(3) . . . . ?
C20 C21 C22 C17 0.2(3) . . . . ?
C20 C21 C22 C25 -179.8(2) . . . . ?
C22 C17 C18 C19 1.9(3) . . . . ?
C22 C17 C18 C23 171.9(10) . . . . ?
C22 C17 C18 C23A -168.2(11) . . . . ?
C24 C20 C21 C22 -179.6(2) . . . . ?
C26 C27 C28 C29 0.6(4) . . . . ?
C27 C26 C31 C30 0.6(3) . . . . ?
C27 C26 S2 C9 -99.1(3) . . . . ?
C27 C26 S2A C9 -91.2(5) . . . . ?
C27 C28 C29 C30 -0.9(3) . . . . ?
C27 C28 C29 C32 -178.5(2) . . . . ?
C28 C29 C30 C31 1.1(3) . . . . ?
C29 C30 C31 C26 -0.9(3) . . . . ?
C31 C26 C27 C28 -0.4(3) . . . . ?
C31 C26 S2 C9 82.8(3) . . . . ?
C31 C26 S2A C9 92.0(6) . . . . ?
C32 C29 C30 C31 178.7(2) . . . . ?
B1 N1 C1 C2 -175.50(19) . . . . ?
B1 N1 C1 S1 2.6(3) . . . . ?
B1 N1 C1 S1A 9.3(6) . . . . ?
B1 N1 C4 C3 175.27(17) . . . . ?
B1 N1 C4 C5 -7.4(3) . . . . ?
B1 N2 C6 C5 11.5(3) . . . . ?
B1 N2 C6 C7 -171.25(17) . . . . ?
B1 N2 C9 C8 171.74(19) . . . . ?
B1 N2 C9 S2 -4.3(4) . . . . ?
B1 N2 C9 S2A -12.7(6) . . . . ?
S1 C1 C2 C3 -176.5(3) . . . . ?
S1 C10 C11 C12 -173.3(2) . . . . ?
S1 C10 C15 C14 175.2(2) . . . . ?
S2 C26 C27 C28 -178.7(2) . . . . ?
S2 C26 C31 C30 178.7(2) . . . . ?
C23 C18 C19 C20 -170.2(10) . . . . ?
S1A C1 C2 C3 176.2(6) . . . . ?
S1A C10 C11 C12 -178.9(4) . . . . ?
S1A C10 C15 C14 -179.3(5) . . . . ?
S2A C26 C27 C28 -177.2(3) . . . . ?
S2A C26 C31 C30 177.6(3) . . . . ?
C23A C18 C19 C20 170.4(10) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.625 0.500 0.500 331.5 61.9 ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT910_20180614b           
;
PROBLEM:  Missing # of FCF Reflection(s) Below Theta(Min).         20 Note 
RESPONSE: The missing FCF reflections below theta(min) were
caused by the high beamstop theta(min) limit set.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_mo_20180805b_0m
_database_code_depnum_ccdc_archive 'CCDC 1871716'
_audit_update_record             
;
2018-10-06 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;
_audit_creation_date             2018-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H35 B F2 N2 S3'
_chemical_formula_sum            'C27 H35 B F2 N2 S3'
_chemical_formula_weight         532.56
_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'
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                   12.2704(8)
_cell_length_b                   15.2656(10)
_cell_length_c                   15.5063(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.898(2)
_cell_angle_gamma                90
_cell_volume                     2861.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.507
_cell_measurement_theta_min      2.982
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1112 before and 0.0745 after correction. The Ratio of minimum to maximum transmission is 0.8082. 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    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44815
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         2.982
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4414
_reflns_number_total             6368
_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       'SAINT v8.37A (Bruker, 2015)'
_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         0.431
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6368
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0812
_refine_ls_restrained_S_all      1.054
_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)+(0.0775P)²+4.0703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1868
_refine_ls_wR_factor_ref         0.2170
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C25-C26A = C26-C25 = C27-C26 = C27A-C26A
 1.54 with sigma of 0.005
 C25-C27 = C25-C27A
 2.52 with sigma of 0.005
 S3-C9 \\sim S3A-C9
 with sigma of 0.02
 S3-C25 \\sim S3A-C25
 with sigma of 0.02
 C11A-C10 \\sim C11-C10 \\sim C12-C11 \\sim C12A-C11A
 with sigma of 0.02
 F1-B1 \\sim F1A-B1 \\sim F2-B1 \\sim F2A-B1
 with sigma of 0.02
 F1-F2 \\sim F1A-F2A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12A) = Uanis(C12)
Uanis(C11A) = Uanis(C11)
Uanis(C27) = Uanis(C27A)
4. Others
 Sof(H10C)=Sof(H10D)=Sof(H25C)=Sof(H25D)=Sof(S3A)=Sof(C26A)=Sof(H26C)=
 Sof(H26D)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12D)=Sof(H12E)=
 Sof(H12F)=Sof(F2)=Sof(C27)=Sof(H27D)=Sof(H27E)=Sof(H27F)=Sof(F1A)=1-FVAR(1)
 Sof(S3)=Sof(F1)=Sof(F2A)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=
 Sof(H26B)=Sof(C27A)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,
 H14B), C25(H25A,H25B), C25(H25C,H25D), C26(H26A,H26B), C26A(H26C,H26D),
 C11A(H11C,H11D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C8(H8), C18(H18), C20(H20)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C27A(H27A,H27B,H27C), C12A(H12D,H12E,H12F),
 C27(H27D,H27E,H27F)
;
_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 0.56308(10) 0.76460(7) 0.59349(6) 0.0718(4) Uani 1 1 d . . . . .
S2 S 0.69468(9) 0.42994(7) 0.50536(6) 0.0645(3) Uani 1 1 d . . . . .
S3 S 0.8083(5) 0.7245(3) 0.9559(3) 0.0652(8) Uani 0.659(6) 1 d D . P A 1
F1 F 0.5965(9) 0.6788(10) 0.7860(11) 0.111(4) Uani 0.659(6) 1 d D . P A 1
F2A F 0.7667(8) 0.7442(4) 0.7530(6) 0.089(2) Uani 0.659(6) 1 d D . P A 2
N1 N 0.6762(2) 0.62672(18) 0.66954(16) 0.0497(6) Uani 1 1 d . . . . .
N2 N 0.7704(2) 0.60770(19) 0.82283(16) 0.0527(7) Uani 1 1 d . . . . .
C1 C 0.6201(3) 0.6615(2) 0.59435(19) 0.0507(7) Uani 1 1 d . . . . .
C2 C 0.6178(3) 0.6012(2) 0.5250(2) 0.0544(8) Uani 1 1 d . . . . .
H2 H 0.585343 0.610188 0.466936 0.065 Uiso 1 1 calc R . . . .
C3 C 0.6724(3) 0.5265(2) 0.5588(2) 0.0505(7) Uani 1 1 d . . . . .
C4 C 0.7092(3) 0.5421(2) 0.65079(19) 0.0471(7) Uani 1 1 d . . . . .
C5 C 0.7666(2) 0.4895(2) 0.7162(2) 0.0479(7) Uani 1 1 d . . . . .
C6 C 0.7954(3) 0.5226(2) 0.8022(2) 0.0513(7) Uani 1 1 d . . . . .
C7 C 0.8537(3) 0.4828(3) 0.8773(2) 0.0630(9) Uani 1 1 d . . . . .
H7 H 0.880810 0.425814 0.881402 0.076 Uiso 1 1 calc R . . . .
C8 C 0.8637(3) 0.5433(3) 0.9444(2) 0.0662(10) Uani 1 1 d . . . . .
H8 H 0.898027 0.534409 1.002007 0.079 Uiso 1 1 calc R . . . .
C9 C 0.8125(3) 0.6207(3) 0.9094(2) 0.0580(9) Uani 1 1 d D . . . .
C10 C 0.5009(4) 0.7782(3) 0.4793(3) 0.0777(12) Uani 1 1 d D . . . .
H10A H 0.551152 0.756464 0.442312 0.093 Uiso 0.659(6) 1 calc R . P A 1
H10B H 0.433116 0.744401 0.466915 0.093 Uiso 0.659(6) 1 calc R . P A 1
H10C H 0.554887 0.797280 0.444347 0.093 Uiso 0.341(6) 1 calc R . P A 2
H10D H 0.466178 0.724544 0.454900 0.093 Uiso 0.341(6) 1 calc R . P A 2
C11 C 0.4757(8) 0.8747(5) 0.4591(5) 0.094(3) Uani 0.659(6) 1 d D . P A 1
H11A H 0.541520 0.909527 0.478261 0.113 Uiso 0.659(6) 1 calc R . P A 1
H11B H 0.453918 0.882547 0.396380 0.113 Uiso 0.659(6) 1 calc R . P A 1
C12 C 0.3828(10) 0.9058(8) 0.5055(7) 0.149(5) Uani 0.659(6) 1 d D . P A 1
H12A H 0.357140 0.962131 0.483185 0.223 Uiso 0.659(6) 1 calc GR . P A 1
H12B H 0.409888 0.910122 0.567227 0.223 Uiso 0.659(6) 1 calc GR . P A 1
H12C H 0.322804 0.864590 0.495354 0.223 Uiso 0.659(6) 1 calc GR . P A 1
C13 C 0.6367(3) 0.4555(3) 0.3918(2) 0.0650(9) Uani 1 1 d . . . . .
H13A H 0.620540 0.401087 0.359810 0.078 Uiso 1 1 calc R . . . .
H13B H 0.567360 0.486437 0.390298 0.078 Uiso 1 1 calc R . . . .
C14 C 0.7109(4) 0.5097(3) 0.3466(3) 0.0784(12) Uani 1 1 d . . . . .
H14A H 0.781022 0.479703 0.348982 0.094 Uiso 1 1 calc R . . . .
H14B H 0.725146 0.565119 0.376970 0.094 Uiso 1 1 calc R . . . .
C15 C 0.6601(5) 0.5270(4) 0.2508(3) 0.1033(17) Uani 1 1 d . . . . .
H15A H 0.645069 0.472257 0.220707 0.155 Uiso 1 1 calc GR . . . .
H15B H 0.710913 0.560508 0.223488 0.155 Uiso 1 1 calc GR . . . .
H15C H 0.592350 0.559179 0.248313 0.155 Uiso 1 1 calc GR . . . .
C16 C 0.7989(3) 0.3973(2) 0.7001(2) 0.0480(7) Uani 1 1 d . . . . .
C17 C 0.9024(3) 0.3788(2) 0.6789(2) 0.0580(8) Uani 1 1 d . . . . .
C18 C 0.9314(3) 0.2925(3) 0.6683(3) 0.0665(10) Uani 1 1 d . . . . .
H18 H 1.000164 0.280291 0.653663 0.080 Uiso 1 1 calc R . . . .
C19 C 0.8616(3) 0.2235(2) 0.6787(3) 0.0642(9) Uani 1 1 d . . . . .
C20 C 0.7603(3) 0.2434(2) 0.6999(3) 0.0641(9) Uani 1 1 d . . . . .
H20 H 0.712579 0.197719 0.707270 0.077 Uiso 1 1 calc R . . . .
C21 C 0.7261(3) 0.3287(2) 0.7107(2) 0.0540(8) Uani 1 1 d . . . . .
C22 C 0.9813(4) 0.4510(3) 0.6649(4) 0.0958(16) Uani 1 1 d . . . . .
H22A H 0.953329 0.481212 0.611303 0.144 Uiso 1 1 calc GR . . . .
H22B H 1.052393 0.426376 0.661426 0.144 Uiso 1 1 calc GR . . . .
H22C H 0.988368 0.491499 0.712880 0.144 Uiso 1 1 calc GR . . . .
C23 C 0.8965(5) 0.1302(3) 0.6661(4) 0.1009(17) Uani 1 1 d . . . . .
H23A H 0.882535 0.116026 0.604906 0.151 Uiso 1 1 calc GR . . . .
H23B H 0.855053 0.091278 0.696920 0.151 Uiso 1 1 calc GR . . . .
H23C H 0.973990 0.123806 0.688619 0.151 Uiso 1 1 calc GR . . . .
C24 C 0.6132(3) 0.3475(3) 0.7313(3) 0.0784(12) Uani 1 1 d . . . . .
H24A H 0.619752 0.386583 0.780483 0.118 Uiso 1 1 calc GR . . . .
H24B H 0.579391 0.293799 0.745205 0.118 Uiso 1 1 calc GR . . . .
H24C H 0.568196 0.374281 0.681497 0.118 Uiso 1 1 calc GR . . . .
C25 C 0.8720(4) 0.7056(3) 1.0690(3) 0.0896(15) Uani 1 1 d D . . . .
H25A H 0.836283 0.741023 1.107962 0.108 Uiso 0.659(6) 1 calc R . P A 1
H25B H 0.865203 0.644430 1.084217 0.108 Uiso 0.659(6) 1 calc R . P A 1
H25C H 0.829539 0.681224 1.110575 0.108 Uiso 0.341(6) 1 calc R . P A 2
H25D H 0.930299 0.664087 1.063542 0.108 Uiso 0.341(6) 1 calc R . P A 2
C26 C 0.9935(5) 0.7309(7) 1.0772(6) 0.125(4) Uani 0.659(6) 1 d D . P A 1
H26A H 1.021516 0.711499 1.025573 0.150 Uiso 0.659(6) 1 calc R . P A 1
H26B H 1.036000 0.701865 1.127732 0.150 Uiso 0.659(6) 1 calc R . P A 1
C27A C 1.0284(10) 0.8130(8) 1.0674(10) 0.151(4) Uani 0.659(6) 1 d D . P A 2
H27A H 1.007521 0.816208 1.004910 0.227 Uiso 0.659(6) 1 calc GR . P A 2
H27B H 1.083490 0.768303 1.082249 0.227 Uiso 0.659(6) 1 calc GR . P A 2
H27C H 1.057927 0.868394 1.089468 0.227 Uiso 0.659(6) 1 calc GR . P A 2
B1 B 0.7003(4) 0.6722(3) 0.7602(2) 0.0625(11) Uani 1 1 d D . . . .
S3A S 0.7809(11) 0.7132(8) 0.9627(7) 0.109(5) Uani 0.341(6) 1 d D . P A 2
C26A C 0.9266(7) 0.7906(5) 1.1082(6) 0.061(3) Uani 0.341(6) 1 d D . P A 2
H26C H 0.873697 0.838304 1.097725 0.073 Uiso 0.341(6) 1 calc R . P A 2
H26D H 0.948495 0.783875 1.170999 0.073 Uiso 0.341(6) 1 calc R . P A 2
C11A C 0.4124(13) 0.8520(11) 0.4864(10) 0.094(3) Uani 0.341(6) 1 d D . P A 2
H11C H 0.450245 0.899857 0.520298 0.113 Uiso 0.341(6) 1 calc R . P A 2
H11D H 0.386452 0.874250 0.427868 0.113 Uiso 0.341(6) 1 calc R . P A 2
C12A C 0.3106(16) 0.8286(15) 0.5266(13) 0.149(5) Uani 0.341(6) 1 d D . P A 2
H12D H 0.252980 0.807299 0.481670 0.223 Uiso 0.341(6) 1 calc GR . P A 2
H12E H 0.285056 0.879753 0.553176 0.223 Uiso 0.341(6) 1 calc GR . P A 2
H12F H 0.329825 0.784023 0.570274 0.223 Uiso 0.341(6) 1 calc GR . P A 2
F2 F 0.7336(16) 0.7569(8) 0.7587(14) 0.133(9) Uani 0.341(6) 1 d D . P A 1
C27 C 1.0079(15) 0.8307(9) 1.087(2) 0.151(4) Uani 0.341(6) 1 d D . P A 1
H27D H 1.010805 0.856338 1.031101 0.227 Uiso 0.341(6) 1 calc GR . P A 1
H27E H 1.075361 0.843303 1.126623 0.227 Uiso 0.341(6) 1 calc GR . P A 1
H27F H 0.946499 0.854846 1.110138 0.227 Uiso 0.341(6) 1 calc GR . P A 1
F1A F 0.6135(16) 0.7056(16) 0.7946(19) 0.086(5) Uani 0.341(6) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.721(3) . ?
S1 C10 1.815(4) . ?
S2 C3 1.736(3) . ?
S2 C13 1.825(4) . ?
S3 C9 1.746(6) . ?
S3 C25 1.816(6) . ?
F1 B1 1.403(8) . ?
F2A B1 1.384(7) . ?
N1 C1 1.357(4) . ?
N1 C4 1.400(4) . ?
N1 B1 1.550(5) . ?
N2 C6 1.385(4) . ?
N2 C9 1.368(4) . ?
N2 B1 1.538(5) . ?
C1 C2 1.413(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(5) . ?
C3 C4 1.441(4) . ?
C4 C5 1.387(4) . ?
C5 C6 1.412(4) . ?
C5 C16 1.495(4) . ?
C6 C7 1.397(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.381(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.402(5) . ?
C9 S3A 1.714(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C10 C11 1.528(8) . ?
C10 C11A 1.582(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.525(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.491(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.531(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.395(5) . ?
C16 C21 1.404(5) . ?
C17 C18 1.382(5) . ?
C17 C22 1.508(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(6) . ?
C19 C20 1.373(6) . ?
C19 C23 1.510(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(5) . ?
C21 C24 1.503(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C25 H25D 0.9700 . ?
C25 C26 1.524(5) . ?
C25 S3A 1.830(11) . ?
C25 C26A 1.538(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.540(5) . ?
C27A H27A 0.9600 . ?
C27A H27B 0.9600 . ?
C27A H27C 0.9600 . ?
C27A C26A 1.532(5) . ?
B1 F2 1.357(12) . ?
B1 F1A 1.369(13) . ?
C26A H26C 0.9700 . ?
C26A H26D 0.9700 . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A C12A 1.532(16) . ?
C12A H12D 0.9600 . ?
C12A H12E 0.9600 . ?
C12A H12F 0.9600 . ?
C27 H27D 0.9600 . ?
C27 H27E 0.9600 . ?
C27 H27F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C10 102.36(17) . . ?
C3 S2 C13 102.21(17) . . ?
C9 S3 C25 102.5(3) . . ?
C1 N1 C4 107.8(3) . . ?
C1 N1 B1 126.4(3) . . ?
C4 N1 B1 125.8(3) . . ?
C6 N2 B1 125.2(3) . . ?
C9 N2 C6 107.5(3) . . ?
C9 N2 B1 127.1(3) . . ?
N1 C1 S1 120.7(2) . . ?
N1 C1 C2 109.8(3) . . ?
C2 C1 S1 129.5(2) . . ?
C1 C2 H2 126.1 . . ?
C3 C2 C1 107.8(3) . . ?
C3 C2 H2 126.1 . . ?
C2 C3 S2 128.8(2) . . ?
C2 C3 C4 106.8(3) . . ?
C4 C3 S2 124.3(3) . . ?
N1 C4 C3 107.8(3) . . ?
C5 C4 N1 120.7(3) . . ?
C5 C4 C3 131.5(3) . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 C16 122.6(3) . . ?
C6 C5 C16 117.6(3) . . ?
N2 C6 C5 121.6(3) . . ?
N2 C6 C7 108.5(3) . . ?
C7 C6 C5 129.9(3) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 C6 107.7(3) . . ?
C8 C7 H7 126.2 . . ?
C7 C8 H8 126.4 . . ?
C7 C8 C9 107.2(3) . . ?
C9 C8 H8 126.4 . . ?
N2 C9 S3 120.2(3) . . ?
N2 C9 C8 109.0(3) . . ?
N2 C9 S3A 120.9(4) . . ?
C8 C9 S3 130.4(3) . . ?
C8 C9 S3A 129.2(5) . . ?
S1 C10 H10A 109.6 . . ?
S1 C10 H10B 109.6 . . ?
S1 C10 H10C 111.6 . . ?
S1 C10 H10D 111.6 . . ?
H10A C10 H10B 108.1 . . ?
H10C C10 H10D 109.4 . . ?
C11 C10 S1 110.3(4) . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C11A C10 S1 101.1(6) . . ?
C11A C10 H10C 111.6 . . ?
C11A C10 H10D 111.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.1(7) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S2 C13 H13A 108.8 . . ?
S2 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 S2 113.8(3) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C13 C14 C15 111.9(4) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C5 120.6(3) . . ?
C17 C16 C21 119.9(3) . . ?
C21 C16 C5 119.4(3) . . ?
C16 C17 C22 121.2(3) . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 C22 119.7(4) . . ?
C17 C18 H18 118.8 . . ?
C17 C18 C19 122.3(4) . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C23 120.6(4) . . ?
C20 C19 C18 117.6(3) . . ?
C20 C19 C23 121.8(4) . . ?
C19 C20 H20 118.6 . . ?
C19 C20 C21 122.8(4) . . ?
C21 C20 H20 118.6 . . ?
C16 C21 C24 120.6(3) . . ?
C20 C21 C16 118.4(3) . . ?
C20 C21 C24 121.0(3) . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
S3 C25 H25A 110.3 . . ?
S3 C25 H25B 110.3 . . ?
H25A C25 H25B 108.6 . . ?
H25C C25 H25D 107.2 . . ?
C26 C25 S3 107.0(5) . . ?
C26 C25 H25A 110.3 . . ?
C26 C25 H25B 110.3 . . ?
S3A C25 H25C 108.0 . . ?
S3A C25 H25D 108.0 . . ?
C26A C25 H25C 108.0 . . ?
C26A C25 H25D 108.0 . . ?
C26A C25 S3A 117.4(6) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 C27 110.6(5) . . ?
H26A C26 H26B 108.1 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H27A C27A H27B 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C26A C27A H27A 109.5 . . ?
C26A C27A H27B 109.5 . . ?
C26A C27A H27C 109.5 . . ?
F1 B1 N1 104.5(7) . . ?
F1 B1 N2 107.6(8) . . ?
F2A B1 N1 107.8(5) . . ?
F2A B1 N2 106.6(5) . . ?
N2 B1 N1 106.6(3) . . ?
F2 B1 F1 103.1(9) . . ?
F2 B1 N1 115.0(10) . . ?
F2 B1 N2 118.9(9) . . ?
F1A B1 F2A 104.1(10) . . ?
F1A B1 N1 118.7(12) . . ?
F1A B1 N2 112.4(14) . . ?
C9 S3A C25 103.2(6) . . ?
C25 C26A H26C 109.5 . . ?
C25 C26A H26D 109.5 . . ?
C27A C26A C25 110.8(4) . . ?
C27A C26A H26C 109.5 . . ?
C27A C26A H26D 109.5 . . ?
H26C C26A H26D 108.1 . . ?
C10 C11A H11C 107.6 . . ?
C10 C11A H11D 107.6 . . ?
H11C C11A H11D 107.1 . . ?
C12A C11A C10 118.7(13) . . ?
C12A C11A H11C 107.6 . . ?
C12A C11A H11D 107.6 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C26 C27 H27D 109.5 . . ?
C26 C27 H27E 109.5 . . ?
C26 C27 H27F 109.5 . . ?
H27D C27 H27E 109.5 . . ?
H27D C27 H27F 109.5 . . ?
H27E C27 H27F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 -178.3(3) . . . . ?
S1 C10 C11 C12 -68.5(8) . . . . ?
S1 C10 C11A C12A -71.0(15) . . . . ?
S2 C3 C4 N1 180.0(2) . . . . ?
S2 C3 C4 C5 -0.3(5) . . . . ?
S2 C13 C14 C15 178.3(3) . . . . ?
S3 C25 C26 C27 81.0(16) . . . . ?
N1 C1 C2 C3 1.1(4) . . . . ?
N1 C4 C5 C6 -2.2(5) . . . . ?
N1 C4 C5 C16 177.1(3) . . . . ?
N2 C6 C7 C8 0.5(4) . . . . ?
N2 C9 S3A C25 -172.1(4) . . . . ?
C1 S1 C10 C11 -163.3(5) . . . . ?
C1 S1 C10 C11A 158.6(8) . . . . ?
C1 N1 C4 C3 1.2(4) . . . . ?
C1 N1 C4 C5 -178.5(3) . . . . ?
C1 N1 B1 F1 68.7(8) . . . . ?
C1 N1 B1 F2A -63.4(6) . . . . ?
C1 N1 B1 N2 -177.5(3) . . . . ?
C1 N1 B1 F2 -43.6(10) . . . . ?
C1 N1 B1 F1A 54.4(15) . . . . ?
C1 C2 C3 S2 179.2(3) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 N1 -0.5(4) . . . . ?
C2 C3 C4 C5 179.2(3) . . . . ?
C3 S2 C13 C14 78.8(3) . . . . ?
C3 C4 C5 C6 178.1(3) . . . . ?
C3 C4 C5 C16 -2.6(5) . . . . ?
C4 N1 C1 S1 178.0(2) . . . . ?
C4 N1 C1 C2 -1.4(4) . . . . ?
C4 N1 B1 F1 -111.6(8) . . . . ?
C4 N1 B1 F2A 116.3(5) . . . . ?
C4 N1 B1 N2 2.2(5) . . . . ?
C4 N1 B1 F2 136.1(10) . . . . ?
C4 N1 B1 F1A -125.8(14) . . . . ?
C4 C5 C6 N2 -1.7(5) . . . . ?
C4 C5 C6 C7 -179.0(4) . . . . ?
C4 C5 C16 C17 93.1(4) . . . . ?
C4 C5 C16 C21 -90.0(4) . . . . ?
C5 C6 C7 C8 178.0(4) . . . . ?
C5 C16 C17 C18 177.1(3) . . . . ?
C5 C16 C17 C22 -4.7(5) . . . . ?
C5 C16 C21 C20 -176.7(3) . . . . ?
C5 C16 C21 C24 4.6(5) . . . . ?
C6 N2 C9 S3 173.8(3) . . . . ?
C6 N2 C9 C8 -0.6(4) . . . . ?
C6 N2 C9 S3A -170.6(6) . . . . ?
C6 N2 B1 F1 105.4(7) . . . . ?
C6 N2 B1 F2A -121.1(5) . . . . ?
C6 N2 B1 N1 -6.2(5) . . . . ?
C6 N2 B1 F2 -138.0(11) . . . . ?
C6 N2 B1 F1A 125.5(11) . . . . ?
C6 C5 C16 C17 -87.6(4) . . . . ?
C6 C5 C16 C21 89.3(4) . . . . ?
C6 C7 C8 C9 -0.8(5) . . . . ?
C7 C8 C9 S3 -172.7(4) . . . . ?
C7 C8 C9 N2 0.8(5) . . . . ?
C7 C8 C9 S3A 169.8(7) . . . . ?
C8 C9 S3A C25 20.1(10) . . . . ?
C9 S3 C25 C26 96.3(5) . . . . ?
C9 N2 C6 C5 -177.7(3) . . . . ?
C9 N2 C6 C7 0.1(4) . . . . ?
C9 N2 B1 F1 -69.6(7) . . . . ?
C9 N2 B1 F2A 63.9(6) . . . . ?
C9 N2 B1 N1 178.8(3) . . . . ?
C9 N2 B1 F2 46.9(11) . . . . ?
C9 N2 B1 F1A -49.6(12) . . . . ?
C10 S1 C1 N1 179.5(3) . . . . ?
C10 S1 C1 C2 -1.2(4) . . . . ?
C13 S2 C3 C2 4.1(4) . . . . ?
C13 S2 C3 C4 -176.5(3) . . . . ?
C16 C5 C6 N2 179.0(3) . . . . ?
C16 C5 C6 C7 1.7(5) . . . . ?
C16 C17 C18 C19 -0.6(6) . . . . ?
C17 C16 C21 C20 0.3(5) . . . . ?
C17 C16 C21 C24 -178.5(3) . . . . ?
C17 C18 C19 C20 0.3(6) . . . . ?
C17 C18 C19 C23 179.8(4) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C19 C20 C21 C16 -0.5(5) . . . . ?
C19 C20 C21 C24 178.2(4) . . . . ?
C21 C16 C17 C18 0.2(5) . . . . ?
C21 C16 C17 C22 178.4(4) . . . . ?
C22 C17 C18 C19 -178.8(4) . . . . ?
C23 C19 C20 C21 -179.2(4) . . . . ?
C25 S3 C9 N2 179.5(3) . . . . ?
C25 S3 C9 C8 -7.5(6) . . . . ?
B1 N1 C1 S1 -2.2(5) . . . . ?
B1 N1 C1 C2 178.3(3) . . . . ?
B1 N1 C4 C3 -178.6(3) . . . . ?
B1 N1 C4 C5 1.7(5) . . . . ?
B1 N2 C6 C5 6.4(5) . . . . ?
B1 N2 C6 C7 -175.8(3) . . . . ?
B1 N2 C9 S3 -10.5(6) . . . . ?
B1 N2 C9 C8 175.2(4) . . . . ?
B1 N2 C9 S3A 5.2(8) . . . . ?
S3A C25 C26A C27A -80.7(11) . . . . ?
C26A C25 S3A C9 140.0(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_20180630b
_database_code_depnum_ccdc_archive 'CCDC 1871715'
_audit_update_record             
;
2018-10-06 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;
_audit_creation_date             2018-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 B F2 N2 S'
_chemical_formula_sum            'C21 H23 B F2 N2 S'
_chemical_formula_weight         384.28
_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'
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                   8.4332(3)
_cell_length_b                   21.5270(9)
_cell_length_c                   11.4689(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.202(2)
_cell_angle_gamma                90
_cell_volume                     2027.05(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9384
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.463
_cell_measurement_theta_min      3.120
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            84176
_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         27.616
_diffrn_reflns_theta_min         2.883
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3844
_reflns_number_total             4657
_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       'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4657
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.042
_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)+(0.0642P)²+0.9796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1418
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F1-B1 \\sim F1A-B1 \\sim F2-B1 \\sim F2A-B1
 with sigma of 0.02
3. Others
 Sof(F1A)=Sof(F2A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C15(H15), C17(H17)
4.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_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 0.29351(8) 0.52055(3) 0.03221(5) 0.0660(2) Uani 1 1 d . . . . .
N1 N 0.23078(17) 0.63040(6) 0.12069(12) 0.0376(3) Uani 1 1 d . . . . .
N2 N 0.38511(16) 0.68802(7) 0.29787(12) 0.0394(3) Uani 1 1 d . . . . .
C1 C 0.1818(2) 0.58799(8) 0.03367(16) 0.0425(4) Uani 1 1 d . . . . .
C2 C 0.0344(2) 0.60792(9) -0.04324(16) 0.0474(4) Uani 1 1 d . . . . .
H2 H -0.024059 0.587099 -0.110463 0.057 Uiso 1 1 calc R . . . .
C3 C -0.0054(2) 0.66332(8) -0.00021(16) 0.0428(4) Uani 1 1 d . . . . .
H3 H -0.096952 0.687054 -0.032752 0.051 Uiso 1 1 calc R . . . .
C4 C 0.11625(19) 0.67847(7) 0.10223(14) 0.0361(3) Uani 1 1 d . . . . .
C5 C 0.13419(19) 0.72996(7) 0.17621(14) 0.0355(3) Uani 1 1 d . . . . .
C6 C 0.27040(19) 0.73513(8) 0.27278(14) 0.0381(3) Uani 1 1 d . . . . .
C7 C 0.3167(2) 0.78224(9) 0.35866(16) 0.0461(4) Uani 1 1 d . . . . .
H7 H 0.261920 0.819372 0.362864 0.055 Uiso 1 1 calc R . . . .
C8 C 0.4590(2) 0.76293(10) 0.43565(17) 0.0531(5) Uani 1 1 d . . . . .
H8 H 0.518371 0.784719 0.501254 0.064 Uiso 1 1 calc R . . . .
C9 C 0.4965(2) 0.70501(10) 0.39673(16) 0.0473(4) Uani 1 1 d . . . . .
H9 H 0.586005 0.681211 0.433620 0.057 Uiso 1 1 calc R . . . .
C10 C 0.2016(3) 0.48612(9) -0.11044(19) 0.0607(5) Uani 1 1 d . . . . .
H10A H 0.233652 0.442801 -0.108966 0.073 Uiso 1 1 calc R . . . .
H10B H 0.084189 0.487422 -0.121286 0.073 Uiso 1 1 calc R . . . .
C11 C 0.2458(3) 0.51677(11) -0.2154(2) 0.0673(6) Uani 1 1 d . . . . .
H11A H 0.363397 0.519182 -0.202226 0.081 Uiso 1 1 calc R . . . .
H11B H 0.203086 0.558786 -0.223369 0.081 Uiso 1 1 calc R . . . .
C12 C 0.1778(5) 0.48104(14) -0.3304(2) 0.0997(11) Uani 1 1 d . . . . .
H12A H 0.203989 0.502624 -0.396767 0.150 Uiso 1 1 calc GR . . . .
H12B H 0.061668 0.477707 -0.342462 0.150 Uiso 1 1 calc GR . . . .
H12C H 0.224857 0.440226 -0.324388 0.150 Uiso 1 1 calc GR . . . .
C13 C 0.00614(19) 0.77905(7) 0.15929(14) 0.0364(3) Uani 1 1 d . . . . .
C14 C 0.0257(2) 0.83493(8) 0.10314(15) 0.0405(4) Uani 1 1 d . . . . .
C15 C -0.0940(2) 0.88045(8) 0.09528(17) 0.0492(4) Uani 1 1 d . . . . .
H15 H -0.081961 0.917841 0.057613 0.059 Uiso 1 1 calc R . . . .
C16 C -0.2302(2) 0.87181(9) 0.14166(18) 0.0521(5) Uani 1 1 d . . . . .
C17 C -0.2472(2) 0.81566(10) 0.19527(17) 0.0509(5) Uani 1 1 d . . . . .
H17 H -0.339184 0.808987 0.225493 0.061 Uiso 1 1 calc R . . . .
C18 C -0.1317(2) 0.76861(8) 0.20576(15) 0.0424(4) Uani 1 1 d . . . . .
C19 C 0.1722(3) 0.84669(10) 0.0515(2) 0.0585(5) Uani 1 1 d . . . . .
H19A H 0.265331 0.855021 0.115310 0.088 Uiso 1 1 calc GR . . . .
H19B H 0.151507 0.881809 -0.001355 0.088 Uiso 1 1 calc GR . . . .
H19C H 0.192981 0.810734 0.007811 0.088 Uiso 1 1 calc GR . . . .
C20 C -0.3568(3) 0.92246(13) 0.1330(3) 0.0838(8) Uani 1 1 d . . . . .
H20A H -0.421166 0.914853 0.190655 0.126 Uiso 1 1 calc GR . . . .
H20B H -0.426117 0.922680 0.053972 0.126 Uiso 1 1 calc GR . . . .
H20C H -0.303553 0.961982 0.149010 0.126 Uiso 1 1 calc GR . . . .
C21 C -0.1537(3) 0.70883(11) 0.2677(2) 0.0635(6) Uani 1 1 d . . . . .
H21A H -0.178717 0.676056 0.209599 0.095 Uiso 1 1 calc GR . . . .
H21B H -0.241329 0.713246 0.307721 0.095 Uiso 1 1 calc GR . . . .
H21C H -0.055082 0.698975 0.325228 0.095 Uiso 1 1 calc GR . . . .
B1 B 0.3818(3) 0.62703(10) 0.2276(2) 0.0488(5) Uani 1 1 d D . . . .
F1 F 0.5154(10) 0.6282(5) 0.1692(10) 0.054(2) Uani 0.42(4) 1 d D . P A 1
F2 F 0.3907(16) 0.5732(5) 0.2902(14) 0.067(2) Uani 0.42(4) 1 d D . P A 1
F1A F 0.5236(9) 0.6160(8) 0.1980(18) 0.094(3) Uani 0.58(4) 1 d D . P A 2
F2A F 0.348(3) 0.5810(5) 0.3051(11) 0.096(3) Uani 0.58(4) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7331(18) . ?
S1 C10 1.802(2) . ?
N1 C1 1.346(2) . ?
N1 C4 1.398(2) . ?
N1 B1 1.555(2) . ?
N2 C6 1.386(2) . ?
N2 C9 1.347(2) . ?
N2 B1 1.538(3) . ?
C1 C2 1.416(3) . ?
C2 C3 1.362(3) . ?
C3 C4 1.410(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.406(2) . ?
C5 C13 1.492(2) . ?
C6 C7 1.406(2) . ?
C7 C8 1.381(3) . ?
C8 C9 1.385(3) . ?
C10 C11 1.493(3) . ?
C11 C12 1.521(3) . ?
C13 C14 1.392(2) . ?
C13 C18 1.403(2) . ?
C14 C15 1.395(2) . ?
C14 C19 1.508(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.378(3) . ?
C16 C20 1.514(3) . ?
C17 C18 1.392(3) . ?
C18 C21 1.502(3) . ?
B1 F1 1.436(7) . ?
B1 F2 1.356(10) . ?
B1 F1A 1.337(8) . ?
B1 F2A 1.403(9) . ?

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 C10 103.37(10) . . ?
C1 N1 C4 107.76(14) . . ?
C1 N1 B1 127.63(15) . . ?
C4 N1 B1 124.54(14) . . ?
C6 N2 B1 126.01(14) . . ?
C9 N2 C6 107.21(15) . . ?
C9 N2 B1 126.76(15) . . ?
N1 C1 S1 119.98(13) . . ?
N1 C1 C2 109.49(15) . . ?
C2 C1 S1 130.49(14) . . ?
C3 C2 C1 107.07(16) . . ?
C2 C3 C4 108.16(16) . . ?
N1 C4 C3 107.51(14) . . ?
C5 C4 N1 121.68(14) . . ?
C5 C4 C3 130.79(15) . . ?
C4 C5 C6 120.12(15) . . ?
C4 C5 C13 120.89(14) . . ?
C6 C5 C13 118.90(14) . . ?
N2 C6 C5 120.78(15) . . ?
N2 C6 C7 108.27(15) . . ?
C7 C6 C5 130.94(16) . . ?
C8 C7 C6 107.01(17) . . ?
C7 C8 C9 107.10(16) . . ?
N2 C9 C8 110.40(16) . . ?
C11 C10 S1 114.58(16) . . ?
C10 C11 C12 111.2(2) . . ?
C14 C13 C5 120.90(14) . . ?
C14 C13 C18 120.69(15) . . ?
C18 C13 C5 118.36(15) . . ?
C13 C14 C15 118.43(16) . . ?
C13 C14 C19 121.41(16) . . ?
C15 C14 C19 120.16(17) . . ?
C16 C15 C14 122.19(18) . . ?
C15 C16 C20 120.9(2) . . ?
C17 C16 C15 118.01(17) . . ?
C17 C16 C20 121.1(2) . . ?
C16 C17 C18 122.30(18) . . ?
C13 C18 C21 121.30(16) . . ?
C17 C18 C13 118.37(17) . . ?
C17 C18 C21 120.32(17) . . ?
N2 B1 N1 106.69(14) . . ?
F1 B1 N1 102.7(5) . . ?
F1 B1 N2 107.9(5) . . ?
F2 B1 N1 113.2(6) . . ?
F2 B1 N2 117.4(7) . . ?
F2 B1 F1 107.9(7) . . ?
F1A B1 N1 115.3(8) . . ?
F1A B1 N2 112.0(5) . . ?
F1A B1 F2A 110.9(5) . . ?
F2A B1 N1 106.6(7) . . ?
F2A B1 N2 104.7(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
