# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_A615RR_0mS

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 B F2 N2 S'
_chemical_formula_weight         300.13

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.019(5)
_cell_length_b                   9.387(5)
_cell_length_c                   9.840(5)
_cell_angle_alpha                103.834(10)
_cell_angle_beta                 111.510(11)
_cell_angle_gamma                104.812(11)
_cell_volume                     696.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            11581
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.395
_diffrn_reflns_theta_max         29.028
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3595
_reflns_number_gt                2442
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3595
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1609
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.12936(9) 0.78017(6) 0.51066(6) 0.0730(2) Uani 1 1 d . . . . .
N1 N 0.35770(19) 1.19701(18) 0.50471(18) 0.0511(4) Uani 1 1 d . . . . .
N2 N 0.32076(18) 1.25630(17) 0.74344(17) 0.0486(4) Uani 1 1 d . . . . .
F1 F 0.59681(14) 1.37089(15) 0.75411(14) 0.0731(4) Uani 1 1 d . . . . .
F2 F 0.39142(17) 1.46064(13) 0.64356(15) 0.0748(4) Uani 1 1 d . . . . .
B1 B 0.4222(3) 1.3285(2) 0.6635(3) 0.0541(5) Uani 1 1 d . . . . .
C1 C 0.3846(3) 1.2088(3) 0.3813(3) 0.0655(5) Uani 1 1 d . . . . .
H1 H 0.4343 1.3037 0.3722 0.079 Uiso 1 1 calc R U . . .
C2 C 0.3278(3) 1.0598(3) 0.2703(3) 0.0694(6) Uani 1 1 d . . . . .
H2 H 0.3297 1.0372 0.1738 0.083 Uiso 1 1 calc R U . . .
C3 C 0.2681(2) 0.9513(2) 0.3280(2) 0.0587(5) Uani 1 1 d . . . . .
H3 H 0.2247 0.8415 0.2793 0.070 Uiso 1 1 calc R U . . .
C4 C 0.2845(2) 1.0365(2) 0.4742(2) 0.0467(4) Uani 1 1 d . . . . .
C5 C 0.2272(2) 0.98478(19) 0.5751(2) 0.0452(4) Uani 1 1 d . . . . .
C6 C 0.2387(2) 1.0951(2) 0.7072(2) 0.0453(4) Uani 1 1 d . . . . .
C7 C 0.1671(3) 1.0811(2) 0.8109(2) 0.0577(5) Uani 1 1 d . . . . .
H7 H 0.1047 0.9872 0.8137 0.069 Uiso 1 1 calc R U . . .
C8 C 0.2066(3) 1.2321(3) 0.9071(3) 0.0694(6) Uani 1 1 d . . . . .
H8 H 0.1761 1.2593 0.9875 0.083 Uiso 1 1 calc R U . . .
C9 C 0.2997(3) 1.3361(2) 0.8627(2) 0.0619(5) Uani 1 1 d . . . . .
H9 H 0.3418 1.4461 0.9090 0.074 Uiso 1 1 calc R U . . .
C10 C 0.1363(2) 0.73556(19) 0.6768(2) 0.0477(4) Uani 1 1 d . . . . .
C11 C -0.0164(2) 0.6453(2) 0.6680(2) 0.0569(5) Uani 1 1 d . . . . .
H11 H -0.1197 0.6131 0.5782 0.068 Uiso 1 1 calc R U . . .
C12 C -0.0147(3) 0.6028(3) 0.7941(3) 0.0655(5) Uani 1 1 d . . . . .
H12 H -0.1171 0.5410 0.7884 0.079 Uiso 1 1 calc R U . . .
C13 C 0.1364(3) 0.6514(3) 0.9264(3) 0.0660(6) Uani 1 1 d . . . . .
H13 H 0.1364 0.6243 1.0113 0.079 Uiso 1 1 calc R U . . .
C14 C 0.2880(3) 0.7398(3) 0.9349(3) 0.0643(5) Uani 1 1 d . . . . .
H14 H 0.3906 0.7726 1.0256 0.077 Uiso 1 1 calc R U . . .
C15 C 0.2894(2) 0.7805(2) 0.8096(2) 0.0575(5) Uani 1 1 d . . . . .
H15 H 0.3930 0.8381 0.8144 0.069 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C5 1.7350(19) . ?
S1 C10 1.766(2) . ?
N1 C1 1.346(3) . ?
N1 C4 1.388(2) . ?
N1 B1 1.532(3) . ?
N2 C9 1.338(3) . ?
N2 C6 1.393(2) . ?
N2 B1 1.543(3) . ?
F1 B1 1.383(2) . ?
F2 B1 1.381(2) . ?
C1 C2 1.380(3) . ?
C2 C3 1.367(3) . ?
C3 C4 1.401(3) . ?
C4 C5 1.403(3) . ?
C5 C6 1.405(3) . ?
C6 C7 1.406(3) . ?
C7 C8 1.373(3) . ?
C8 C9 1.379(3) . ?
C10 C11 1.379(3) . ?
C10 C15 1.381(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.363(3) . ?
C13 C14 1.366(3) . ?
C14 C15 1.379(3) . ?

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
C5 S1 C10 106.67(9) . . ?
C1 N1 C4 107.05(16) . . ?
C1 N1 B1 128.19(17) . . ?
C4 N1 B1 123.91(16) . . ?
C9 N2 C6 107.52(17) . . ?
C9 N2 B1 126.54(17) . . ?
C6 N2 B1 125.92(16) . . ?
F2 B1 F1 109.29(16) . . ?
F2 B1 N1 111.10(17) . . ?
F1 B1 N1 110.44(18) . . ?
F2 B1 N2 110.61(18) . . ?
F1 B1 N2 109.96(17) . . ?
N1 B1 N2 105.40(15) . . ?
N1 C1 C2 110.12(19) . . ?
C3 C2 C1 107.6(2) . . ?
C2 C3 C4 107.2(2) . . ?
N1 C4 C3 108.02(16) . . ?
N1 C4 C5 120.91(16) . . ?
C3 C4 C5 130.78(18) . . ?
C4 C5 C6 120.42(16) . . ?
C4 C5 S1 113.70(13) . . ?
C6 C5 S1 125.67(14) . . ?
N2 C6 C5 118.89(16) . . ?
N2 C6 C7 107.47(15) . . ?
C5 C6 C7 133.28(17) . . ?
C8 C7 C6 107.20(19) . . ?
C7 C8 C9 107.47(19) . . ?
N2 C9 C8 110.35(18) . . ?
C11 C10 C15 119.86(19) . . ?
C11 C10 S1 118.00(15) . . ?
C15 C10 S1 122.04(15) . . ?
C10 C11 C12 119.48(19) . . ?
C13 C12 C11 120.27(19) . . ?
C12 C13 C14 120.3(2) . . ?
C13 C14 C15 120.3(2) . . ?
C14 C15 C10 119.75(19) . . ?

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 N1 B1 F2 48.0(3) . . . . ?
C4 N1 B1 F2 -143.94(17) . . . . ?
C1 N1 B1 F1 -73.5(2) . . . . ?
C4 N1 B1 F1 94.6(2) . . . . ?
C1 N1 B1 N2 167.82(17) . . . . ?
C4 N1 B1 N2 -24.1(2) . . . . ?
C9 N2 B1 F2 -41.2(2) . . . . ?
C6 N2 B1 F2 140.93(17) . . . . ?
C9 N2 B1 F1 79.6(2) . . . . ?
C6 N2 B1 F1 -98.3(2) . . . . ?
C9 N2 B1 N1 -161.34(16) . . . . ?
C6 N2 B1 N1 20.8(2) . . . . ?
C4 N1 C1 C2 1.1(2) . . . . ?
B1 N1 C1 C2 170.73(18) . . . . ?
N1 C1 C2 C3 -1.8(3) . . . . ?
C1 C2 C3 C4 1.7(2) . . . . ?
C1 N1 C4 C3 0.0(2) . . . . ?
B1 N1 C4 C3 -170.18(17) . . . . ?
C1 N1 C4 C5 -174.46(17) . . . . ?
B1 N1 C4 C5 15.3(3) . . . . ?
C2 C3 C4 N1 -1.1(2) . . . . ?
C2 C3 C4 C5 172.65(19) . . . . ?
N1 C4 C5 C6 1.7(3) . . . . ?
C3 C4 C5 C6 -171.39(18) . . . . ?
N1 C4 C5 S1 176.71(12) . . . . ?
C3 C4 C5 S1 3.6(3) . . . . ?
C10 S1 C5 C4 159.70(13) . . . . ?
C10 S1 C5 C6 -25.61(18) . . . . ?
C9 N2 C6 C5 173.79(16) . . . . ?
B1 N2 C6 C5 -8.0(2) . . . . ?
C9 N2 C6 C7 -0.16(19) . . . . ?
B1 N2 C6 C7 178.06(16) . . . . ?
C4 C5 C6 N2 -5.3(2) . . . . ?
S1 C5 C6 N2 -179.62(12) . . . . ?
C4 C5 C6 C7 166.81(19) . . . . ?
S1 C5 C6 C7 -7.6(3) . . . . ?
N2 C6 C7 C8 -0.1(2) . . . . ?
C5 C6 C7 C8 -172.8(2) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C6 N2 C9 C8 0.3(2) . . . . ?
B1 N2 C9 C8 -177.89(17) . . . . ?
C7 C8 C9 N2 -0.4(3) . . . . ?
C5 S1 C10 C11 126.05(16) . . . . ?
C5 S1 C10 C15 -57.63(17) . . . . ?
C15 C10 C11 C12 1.1(3) . . . . ?
S1 C10 C11 C12 177.50(15) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C10 1.8(3) . . . . ?
C11 C10 C15 C14 -2.4(3) . . . . ?
S1 C10 C15 C14 -178.61(15) . . . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 959249'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_609RR_0mS

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 B F2 N2 S2'
_chemical_formula_weight         408.28

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.144(4)
_cell_length_b                   9.856(4)
_cell_length_c                   11.616(4)
_cell_angle_alpha                83.242(6)
_cell_angle_beta                 75.289(6)
_cell_angle_gamma                68.965(7)
_cell_volume                     944.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            9151
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.813
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3703
_reflns_number_gt                2557
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²+0.7034P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3703
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   0.747
_refine_ls_restrained_S_all      0.747
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.70675(9) -0.16441(8) 0.10871(6) 0.0583(2) Uani 1 1 d . . . . .
S2 S 0.83855(12) 0.45147(9) -0.03484(8) 0.0745(3) Uani 1 1 d . . . . .
B1 B 0.8968(4) 0.2059(3) 0.1693(3) 0.0483(7) Uani 1 1 d . . . . .
N1 N 0.8235(2) 0.1969(2) 0.06346(17) 0.0442(5) Uani 1 1 d . . . . .
N2 N 0.9187(3) 0.0612(2) 0.23892(18) 0.0484(5) Uani 1 1 d . . . . .
F1 F 1.04176(19) 0.22642(19) 0.12661(14) 0.0644(4) Uani 1 1 d . . . . .
F2 F 0.7907(2) 0.32042(16) 0.24012(13) 0.0637(4) Uani 1 1 d . . . . .
C1 C 1.0027(4) 0.0121(4) 0.3247(2) 0.0595(7) Uani 1 1 d . . . . .
H1 H 1.058(4) 0.065(3) 0.344(3) 0.068(9) Uiso 1 1 d . . . . .
C2 C 0.9965(4) -0.1213(4) 0.3680(3) 0.0642(8) Uani 1 1 d . . . . .
H2 H 1.048(4) -0.177(3) 0.425(3) 0.069(9) Uiso 1 1 d . . . . .
C3 C 0.9064(3) -0.1581(3) 0.3072(2) 0.0554(7) Uani 1 1 d . . . . .
H3 H 0.882(3) -0.245(3) 0.316(2) 0.060(8) Uiso 1 1 d . . . . .
C4 C 0.8585(3) -0.0444(3) 0.2255(2) 0.0466(6) Uani 1 1 d . . . . .
C5 C 0.7779(3) -0.0289(3) 0.1332(2) 0.0452(6) Uani 1 1 d . . . . .
C6 C 0.7643(3) 0.0870(3) 0.0527(2) 0.0447(5) Uani 1 1 d . . . . .
C7 C 0.6995(3) 0.1213(3) -0.0496(2) 0.0517(6) Uani 1 1 d . . . . .
H7 H 0.654(3) 0.063(3) -0.079(2) 0.055(7) Uiso 1 1 d . . . . .
C8 C 0.7188(3) 0.2462(3) -0.0992(2) 0.0531(6) Uani 1 1 d . . . . .
H8 H 0.693(3) 0.297(3) -0.165(3) 0.060(8) Uiso 1 1 d . . . . .
C9 C 0.7937(3) 0.2938(3) -0.0265(2) 0.0484(6) Uani 1 1 d . . . . .
C10 C 0.5848(3) -0.1884(3) 0.2500(2) 0.0466(6) Uani 1 1 d . . . . .
C11 C 0.5821(4) -0.3264(3) 0.2802(3) 0.0579(7) Uani 1 1 d . . . . .
H11 H 0.644(4) -0.399(4) 0.237(3) 0.073(10) Uiso 1 1 d . . . . .
C12 C 0.4811(5) -0.3507(4) 0.3836(3) 0.0730(9) Uani 1 1 d . . . . .
H12 H 0.466(5) -0.435(4) 0.398(4) 0.106(13) Uiso 1 1 d . . . . .
C13 C 0.3873(5) -0.2396(5) 0.4587(3) 0.0775(10) Uani 1 1 d . . . . .
H13 H 0.319(4) -0.258(4) 0.524(3) 0.092(11) Uiso 1 1 d . . . . .
C14 C 0.3926(4) -0.1034(4) 0.4295(3) 0.0736(9) Uani 1 1 d . . . . .
H14 H 0.330(4) -0.031(4) 0.476(3) 0.071(10) Uiso 1 1 d . . . . .
C15 C 0.4886(4) -0.0766(3) 0.3248(3) 0.0644(8) Uani 1 1 d . . . . .
H15 H 0.495(4) 0.016(4) 0.307(3) 0.080(10) Uiso 1 1 d . . . . .
C16 C 0.7897(3) 0.5341(3) -0.1703(2) 0.0549(7) Uani 1 1 d . . . . .
C17 C 0.9125(4) 0.5459(3) -0.2630(3) 0.0650(8) Uani 1 1 d . . . . .
H17 H 1.024(4) 0.503(3) -0.251(3) 0.077(10) Uiso 1 1 d . . . . .
C18 C 0.8763(5) 0.6166(4) -0.3684(3) 0.0791(10) Uani 1 1 d . . . . .
H18 H 0.968(5) 0.618(4) -0.430(3) 0.090(11) Uiso 1 1 d . . . . .
C19 C 0.7213(5) 0.6726(4) -0.3803(3) 0.0800(10) Uani 1 1 d . . . . .
H19 H 0.685(5) 0.724(4) -0.454(4) 0.102(12) Uiso 1 1 d . . . . .
C20 C 0.5999(5) 0.6631(4) -0.2881(4) 0.0780(10) Uani 1 1 d . . . . .
H20 H 0.489(5) 0.702(4) -0.294(4) 0.110(13) Uiso 1 1 d . . . . .
C21 C 0.6318(4) 0.5958(3) -0.1821(3) 0.0676(8) Uani 1 1 d . . . . .
H21 H 0.558(4) 0.589(4) -0.119(3) 0.087(11) Uiso 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 C5 1.759(2) . ?
S1 C10 1.778(3) . ?
S2 C9 1.731(3) . ?
S2 C16 1.770(3) . ?
B1 F1 1.371(3) . ?
B1 F2 1.385(3) . ?
B1 N2 1.528(4) . ?
B1 N1 1.567(3) . ?
N1 C9 1.342(3) . ?
N1 C6 1.404(3) . ?
N2 C1 1.351(3) . ?
N2 C4 1.380(3) . ?
C1 C2 1.367(4) . ?
C1 H1 0.93(3) . ?
C2 C3 1.371(4) . ?
C2 H2 0.92(3) . ?
C3 C4 1.399(4) . ?
C3 H3 0.94(3) . ?
C4 C5 1.413(3) . ?
C5 C6 1.379(3) . ?
C6 C7 1.413(3) . ?
C7 C8 1.347(4) . ?
C7 H7 0.95(3) . ?
C8 C9 1.421(4) . ?
C8 H8 0.90(3) . ?
C10 C11 1.372(4) . ?
C10 C15 1.372(4) . ?
C11 C12 1.372(5) . ?
C11 H11 0.85(3) . ?
C12 C13 1.367(5) . ?
C12 H12 0.89(4) . ?
C13 C14 1.360(5) . ?
C13 H13 0.90(4) . ?
C14 C15 1.368(5) . ?
C14 H14 0.87(3) . ?
C15 H15 0.93(3) . ?
C16 C17 1.373(4) . ?
C16 C21 1.387(4) . ?
C17 C18 1.390(5) . ?
C17 H17 1.00(3) . ?
C18 C19 1.361(5) . ?
C18 H18 0.96(4) . ?
C19 C20 1.355(5) . ?
C19 H19 1.01(4) . ?
C20 C21 1.376(5) . ?
C20 H20 0.96(4) . ?
C21 H21 0.87(4) . ?

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
C5 S1 C10 103.36(11) . . ?
C9 S2 C16 102.34(12) . . ?
F1 B1 F2 109.9(2) . . ?
F1 B1 N2 110.6(2) . . ?
F2 B1 N2 110.7(2) . . ?
F1 B1 N1 110.2(2) . . ?
F2 B1 N1 109.1(2) . . ?
N2 B1 N1 106.2(2) . . ?
C9 N1 C6 107.44(19) . . ?
C9 N1 B1 128.1(2) . . ?
C6 N1 B1 124.3(2) . . ?
C1 N2 C4 107.1(2) . . ?
C1 N2 B1 126.1(2) . . ?
C4 N2 B1 126.7(2) . . ?
N2 C1 C2 110.3(3) . . ?
N2 C1 H1 120.7(19) . . ?
C2 C1 H1 128.9(19) . . ?
C1 C2 C3 107.4(3) . . ?
C1 C2 H2 125.6(19) . . ?
C3 C2 H2 127.0(19) . . ?
C2 C3 C4 107.4(3) . . ?
C2 C3 H3 127.5(17) . . ?
C4 C3 H3 125.1(17) . . ?
N2 C4 C3 107.8(2) . . ?
N2 C4 C5 119.7(2) . . ?
C3 C4 C5 132.2(2) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 S1 117.31(19) . . ?
C4 C5 S1 121.30(19) . . ?
C5 C6 N1 120.8(2) . . ?
C5 C6 C7 131.7(2) . . ?
N1 C6 C7 107.5(2) . . ?
C8 C7 C6 108.3(2) . . ?
C8 C7 H7 126.8(16) . . ?
C6 C7 H7 124.9(16) . . ?
C7 C8 C9 107.3(2) . . ?
C7 C8 H8 131.1(18) . . ?
C9 C8 H8 121.6(18) . . ?
N1 C9 C8 109.5(2) . . ?
N1 C9 S2 119.89(19) . . ?
C8 C9 S2 130.6(2) . . ?
C11 C10 C15 119.7(3) . . ?
C11 C10 S1 116.5(2) . . ?
C15 C10 S1 123.7(2) . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 122(2) . . ?
C12 C11 H11 118(2) . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 118(3) . . ?
C11 C12 H12 121(3) . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 122(2) . . ?
C12 C13 H13 118(2) . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 120(2) . . ?
C15 C14 H14 119(2) . . ?
C14 C15 C10 120.0(3) . . ?
C14 C15 H15 120(2) . . ?
C10 C15 H15 120(2) . . ?
C17 C16 C21 119.7(3) . . ?
C17 C16 S2 118.1(2) . . ?
C21 C16 S2 122.1(2) . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 H17 118.0(19) . . ?
C18 C17 H17 122.8(19) . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 125(2) . . ?
C17 C18 H18 115(2) . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19 114(2) . . ?
C18 C19 H19 126(2) . . ?
C19 C20 C21 120.5(4) . . ?
C19 C20 H20 122(2) . . ?
C21 C20 H20 118(2) . . ?
C20 C21 C16 119.8(3) . . ?
C20 C21 H21 124(2) . . ?
C16 C21 H21 116(2) . . ?

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 B1 N1 C9 -55.0(3) . . . . ?
F2 B1 N1 C9 65.7(3) . . . . ?
N2 B1 N1 C9 -174.9(2) . . . . ?
F1 B1 N1 C6 130.5(2) . . . . ?
F2 B1 N1 C6 -108.8(3) . . . . ?
N2 B1 N1 C6 10.6(3) . . . . ?
F1 B1 N2 C1 48.5(3) . . . . ?
F2 B1 N2 C1 -73.6(3) . . . . ?
N1 B1 N2 C1 168.1(2) . . . . ?
F1 B1 N2 C4 -130.7(2) . . . . ?
F2 B1 N2 C4 107.2(3) . . . . ?
N1 B1 N2 C4 -11.1(3) . . . . ?
C4 N2 C1 C2 -0.8(3) . . . . ?
B1 N2 C1 C2 179.8(2) . . . . ?
N2 C1 C2 C3 0.4(4) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 N2 C4 C3 0.9(3) . . . . ?
B1 N2 C4 C3 -179.7(2) . . . . ?
C1 N2 C4 C5 -173.9(2) . . . . ?
B1 N2 C4 C5 5.4(4) . . . . ?
C2 C3 C4 N2 -0.7(3) . . . . ?
C2 C3 C4 C5 173.2(3) . . . . ?
N2 C4 C5 C6 2.9(4) . . . . ?
C3 C4 C5 C6 -170.5(3) . . . . ?
N2 C4 C5 S1 177.24(17) . . . . ?
C3 C4 C5 S1 3.9(4) . . . . ?
C10 S1 C5 C6 -131.1(2) . . . . ?
C10 S1 C5 C4 54.3(2) . . . . ?
C4 C5 C6 N1 -3.1(4) . . . . ?
S1 C5 C6 N1 -177.68(17) . . . . ?
C4 C5 C6 C7 175.6(3) . . . . ?
S1 C5 C6 C7 1.1(4) . . . . ?
C9 N1 C6 C5 179.9(2) . . . . ?
B1 N1 C6 C5 -4.6(4) . . . . ?
C9 N1 C6 C7 0.9(3) . . . . ?
B1 N1 C6 C7 176.3(2) . . . . ?
C5 C6 C7 C8 -178.6(3) . . . . ?
N1 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C6 N1 C9 C8 -1.7(3) . . . . ?
B1 N1 C9 C8 -176.9(2) . . . . ?
C6 N1 C9 S2 175.52(18) . . . . ?
B1 N1 C9 S2 0.3(3) . . . . ?
C7 C8 C9 N1 1.8(3) . . . . ?
C7 C8 C9 S2 -174.9(2) . . . . ?
C16 S2 C9 N1 176.6(2) . . . . ?
C16 S2 C9 C8 -6.9(3) . . . . ?
C5 S1 C10 C11 -146.3(2) . . . . ?
C5 S1 C10 C15 37.7(3) . . . . ?
C15 C10 C11 C12 1.2(4) . . . . ?
S1 C10 C11 C12 -174.9(2) . . . . ?
C10 C11 C12 C13 -2.3(5) . . . . ?
C11 C12 C13 C14 1.1(5) . . . . ?
C12 C13 C14 C15 1.2(5) . . . . ?
C13 C14 C15 C10 -2.2(5) . . . . ?
C11 C10 C15 C14 1.0(5) . . . . ?
S1 C10 C15 C14 176.9(3) . . . . ?
C9 S2 C16 C17 -113.4(2) . . . . ?
C9 S2 C16 C21 71.4(3) . . . . ?
C21 C16 C17 C18 -1.6(4) . . . . ?
S2 C16 C17 C18 -176.9(2) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C17 C18 C19 C20 1.7(5) . . . . ?
C18 C19 C20 C21 -0.6(6) . . . . ?
C19 C20 C21 C16 -1.6(5) . . . . ?
C17 C16 C21 C20 2.7(5) . . . . ?
S2 C16 C21 C20 177.8(3) . . . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 959246'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_786RRA_0mS

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 B F2 N2 S3'
_chemical_formula_weight         516.43

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.462(3)
_cell_length_b                   12.722(4)
_cell_length_c                   20.648(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.442(6)
_cell_angle_gamma                90
_cell_volume                     2451.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.337
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23599
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.887
_diffrn_reflns_theta_max         25.897
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4742
_reflns_number_gt                3199
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.2019P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4742
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1857
_refine_ls_wR_factor_gt          0.1616
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.74790(12) -0.01698(10) 0.18644(5) 0.0997(5) Uani 1 1 d . . . . .
S2 S 0.19952(10) 0.22324(8) 0.13721(5) 0.0727(3) Uani 1 1 d . . . . .
S3 S 0.57706(15) 0.19133(7) -0.10618(5) 0.0933(4) Uani 1 1 d . . . . .
F1 F 0.5609(2) 0.19713(13) 0.16157(8) 0.0644(5) Uani 1 1 d . . . . .
F2 F 0.42634(19) 0.05135(13) 0.13811(9) 0.0621(5) Uani 1 1 d . . . . .
N1 N 0.6197(3) 0.08222(18) 0.07763(12) 0.0547(6) Uani 1 1 d . . . . .
N2 N 0.3974(3) 0.19014(17) 0.05888(11) 0.0491(6) Uani 1 1 d . . . . .
B1 B 0.5006(4) 0.1302(2) 0.11232(17) 0.0500(8) Uani 1 1 d . . . . .
C1 C 0.7296(4) 0.0194(2) 0.10479(16) 0.0621(8) Uani 1 1 d . . . . .
C2 C 0.8184(4) -0.0007(3) 0.05755(17) 0.0677(9) Uani 1 1 d . . . . .
H2 H 0.8991 -0.0435 0.0630 0.081 Uiso 1 1 calc R U . . .
C3 C 0.7641(4) 0.0539(2) 0.00279(17) 0.0664(9) Uani 1 1 d . . . . .
H3 H 0.8032 0.0565 -0.0357 0.080 Uiso 1 1 calc R U . . .
C4 C 0.6395(4) 0.1058(2) 0.01359(15) 0.0564(8) Uani 1 1 d . . . . .
C5 C 0.5429(4) 0.1694(2) -0.02616(15) 0.0608(8) Uani 1 1 d . . . . .
C6 C 0.4207(4) 0.2082(2) -0.00508(14) 0.0550(8) Uani 1 1 d . . . . .
C7 C 0.2998(4) 0.2603(2) -0.03848(16) 0.0639(9) Uani 1 1 d . . . . .
H7 H 0.2864 0.2818 -0.0821 0.077 Uiso 1 1 calc R U . . .
C8 C 0.2052(4) 0.2740(2) 0.00411(16) 0.0615(8) Uani 1 1 d . . . . .
H8 H 0.1162 0.3065 -0.0050 0.074 Uiso 1 1 calc R U . . .
C9 C 0.2678(4) 0.2298(2) 0.06399(15) 0.0544(8) Uani 1 1 d . . . . .
C10 C 0.8996(4) -0.1001(3) 0.19478(15) 0.0603(8) Uani 1 1 d . . . . .
C11 C 1.0340(5) -0.0596(3) 0.1967(2) 0.0897(12) Uani 1 1 d . . . . .
H11 H 1.0459 0.0121 0.1906 0.108 Uiso 1 1 calc R U . . .
C12 C 1.1519(5) -0.1246(6) 0.2076(3) 0.123(2) Uani 1 1 d . . . . .
H12 H 1.2436 -0.0974 0.2090 0.147 Uiso 1 1 calc R U . . .
C13 C 1.1321(8) -0.2297(7) 0.2164(3) 0.131(3) Uani 1 1 d . . . . .
H13 H 1.2113 -0.2740 0.2235 0.157 Uiso 1 1 calc R U . . .
C14 C 0.9998(8) -0.2705(4) 0.2151(2) 0.1095(18) Uani 1 1 d . . . . .
H14 H 0.9883 -0.3422 0.2211 0.131 Uiso 1 1 calc R U . . .
C15 C 0.8815(5) -0.2050(3) 0.20453(16) 0.0756(10) Uani 1 1 d . . . . .
H15 H 0.7901 -0.2323 0.2041 0.091 Uiso 1 1 calc R U . . .
C16 C 0.0596(3) 0.3170(2) 0.12063(15) 0.0564(8) Uani 1 1 d . . . . .
C17 C 0.0889(4) 0.4225(3) 0.11935(18) 0.0715(9) Uani 1 1 d . . . . .
H17 H 0.1834 0.4455 0.1270 0.086 Uiso 1 1 calc R U . . .
C18 C -0.0215(4) 0.4950(3) 0.10675(19) 0.0789(11) Uani 1 1 d . . . . .
H18 H -0.0011 0.5663 0.1044 0.095 Uiso 1 1 calc R U . . .
C19 C -0.1597(4) 0.4617(3) 0.09791(19) 0.0772(10) Uani 1 1 d . . . . .
H19 H -0.2337 0.5104 0.0896 0.093 Uiso 1 1 calc R U . . .
C20 C -0.1906(4) 0.3577(3) 0.10110(19) 0.0800(11) Uani 1 1 d . . . . .
H20 H -0.2855 0.3356 0.0960 0.096 Uiso 1 1 calc R U . . .
C21 C -0.0808(4) 0.2848(3) 0.11189(17) 0.0666(9) Uani 1 1 d . . . . .
H21 H -0.1022 0.2135 0.1132 0.080 Uiso 1 1 calc R U . . .
C22 C 0.5478(3) 0.3272(2) -0.12009(14) 0.0543(7) Uani 1 1 d . . . . .
C23 C 0.4995(4) 0.3567(3) -0.18388(15) 0.0621(8) Uani 1 1 d . . . . .
H23 H 0.4787 0.3059 -0.2165 0.075 Uiso 1 1 calc R U . . .
C24 C 0.4820(4) 0.4618(3) -0.19934(18) 0.0745(10) Uani 1 1 d . . . . .
H24 H 0.4513 0.4818 -0.2427 0.089 Uiso 1 1 calc R U . . .
C25 C 0.5092(4) 0.5363(3) -0.1519(2) 0.0760(11) Uani 1 1 d . . . . .
H25 H 0.4952 0.6069 -0.1627 0.091 Uiso 1 1 calc R U . . .
C26 C 0.5569(4) 0.5078(3) -0.08848(19) 0.0698(9) Uani 1 1 d . . . . .
H26 H 0.5739 0.5589 -0.0560 0.084 Uiso 1 1 calc R U . . .
C27 C 0.5801(4) 0.4037(3) -0.07245(16) 0.0646(9) Uani 1 1 d . . . . .
H27 H 0.6176 0.3847 -0.0296 0.078 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.729(3) . ?
S1 C10 1.768(3) . ?
S2 C9 1.741(3) . ?
S2 C16 1.773(3) . ?
S3 C5 1.757(3) . ?
S3 C22 1.767(3) . ?
F1 B1 1.376(4) . ?
F2 B1 1.381(4) . ?
N1 C1 1.357(4) . ?
N1 C4 1.398(4) . ?
N1 B1 1.556(4) . ?
N2 C9 1.345(4) . ?
N2 C6 1.393(4) . ?
N2 B1 1.549(4) . ?
C1 C2 1.411(4) . ?
C2 C3 1.354(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C5 C6 1.390(5) . ?
C6 C7 1.402(5) . ?
C7 C8 1.365(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.398(4) . ?
C8 H8 0.9300 . ?
C10 C15 1.365(5) . ?
C10 C11 1.367(5) . ?
C11 C12 1.378(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.351(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.372(5) . ?
C16 C21 1.374(5) . ?
C17 C18 1.386(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.358(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.374(4) . ?
C22 C27 1.382(4) . ?
C23 C24 1.378(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.358(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.362(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.374(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C10 101.81(15) . . ?
C9 S2 C16 99.91(14) . . ?
C5 S3 C22 105.08(13) . . ?
C1 N1 C4 107.8(2) . . ?
C1 N1 B1 127.2(3) . . ?
C4 N1 B1 124.8(2) . . ?
C9 N2 C6 107.5(2) . . ?
C9 N2 B1 127.2(2) . . ?
C6 N2 B1 125.2(3) . . ?
F1 B1 F2 109.9(3) . . ?
F1 B1 N2 111.0(2) . . ?
F2 B1 N2 109.3(3) . . ?
F1 B1 N1 109.8(3) . . ?
F2 B1 N1 110.2(2) . . ?
N2 B1 N1 106.6(2) . . ?
N1 C1 C2 108.9(3) . . ?
N1 C1 S1 120.5(2) . . ?
C2 C1 S1 130.5(3) . . ?
C3 C2 C1 107.3(3) . . ?
C3 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
C2 C3 C4 108.8(3) . . ?
C2 C3 H3 125.6 . . ?
C4 C3 H3 125.6 . . ?
C5 C4 N1 120.6(3) . . ?
C5 C4 C3 132.2(3) . . ?
N1 C4 C3 107.2(3) . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 S3 116.4(2) . . ?
C6 C5 S3 121.9(2) . . ?
C5 C6 N2 120.5(3) . . ?
C5 C6 C7 131.8(3) . . ?
N2 C6 C7 107.5(3) . . ?
C8 C7 C6 108.2(3) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
C7 C8 C9 106.9(3) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 109.9(3) . . ?
N2 C9 S2 121.5(2) . . ?
C8 C9 S2 128.6(3) . . ?
C15 C10 C11 120.2(3) . . ?
C15 C10 S1 118.6(3) . . ?
C11 C10 S1 120.9(3) . . ?
C10 C11 C12 120.2(5) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.0(5) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 121.3(5) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 119.7(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 119.6(4) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C21 118.9(3) . . ?
C17 C16 S2 121.0(3) . . ?
C21 C16 S2 120.0(2) . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 119.9(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C16 C21 C20 120.4(3) . . ?
C16 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C27 119.4(3) . . ?
C23 C22 S3 116.2(2) . . ?
C27 C22 S3 124.2(2) . . ?
C22 C23 C24 119.7(3) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.1(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C27 120.2(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C22 119.9(3) . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?

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
C9 N2 B1 F1 -71.7(4) . . . . ?
C6 N2 B1 F1 111.6(3) . . . . ?
C9 N2 B1 F2 49.7(4) . . . . ?
C6 N2 B1 F2 -127.0(3) . . . . ?
C9 N2 B1 N1 168.8(3) . . . . ?
C6 N2 B1 N1 -7.9(4) . . . . ?
C1 N1 B1 F1 62.8(4) . . . . ?
C4 N1 B1 F1 -110.4(3) . . . . ?
C1 N1 B1 F2 -58.4(4) . . . . ?
C4 N1 B1 F2 128.4(3) . . . . ?
C1 N1 B1 N2 -176.9(3) . . . . ?
C4 N1 B1 N2 9.9(4) . . . . ?
C4 N1 C1 C2 -1.9(4) . . . . ?
B1 N1 C1 C2 -176.1(3) . . . . ?
C4 N1 C1 S1 174.8(2) . . . . ?
B1 N1 C1 S1 0.7(4) . . . . ?
C10 S1 C1 N1 177.9(3) . . . . ?
C10 S1 C1 C2 -6.2(4) . . . . ?
N1 C1 C2 C3 2.4(4) . . . . ?
S1 C1 C2 C3 -173.9(3) . . . . ?
C1 C2 C3 C4 -1.9(4) . . . . ?
C1 N1 C4 C5 -179.9(3) . . . . ?
B1 N1 C4 C5 -5.5(5) . . . . ?
C1 N1 C4 C3 0.7(3) . . . . ?
B1 N1 C4 C3 175.1(3) . . . . ?
C2 C3 C4 C5 -178.5(4) . . . . ?
C2 C3 C4 N1 0.8(4) . . . . ?
N1 C4 C5 C6 -2.7(5) . . . . ?
C3 C4 C5 C6 176.5(3) . . . . ?
N1 C4 C5 S3 -178.8(2) . . . . ?
C3 C4 C5 S3 0.4(5) . . . . ?
C22 S3 C5 C4 -136.1(3) . . . . ?
C22 S3 C5 C6 47.8(3) . . . . ?
C4 C5 C6 N2 4.7(5) . . . . ?
S3 C5 C6 N2 -179.4(2) . . . . ?
C4 C5 C6 C7 -169.8(3) . . . . ?
S3 C5 C6 C7 6.1(5) . . . . ?
C9 N2 C6 C5 -175.7(3) . . . . ?
B1 N2 C6 C5 1.5(4) . . . . ?
C9 N2 C6 C7 0.0(3) . . . . ?
B1 N2 C6 C7 177.2(3) . . . . ?
C5 C6 C7 C8 175.2(3) . . . . ?
N2 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C6 N2 C9 C8 -0.1(3) . . . . ?
B1 N2 C9 C8 -177.3(3) . . . . ?
C6 N2 C9 S2 -179.7(2) . . . . ?
B1 N2 C9 S2 3.1(4) . . . . ?
C7 C8 C9 N2 0.2(4) . . . . ?
C7 C8 C9 S2 179.7(3) . . . . ?
C16 S2 C9 N2 164.2(3) . . . . ?
C16 S2 C9 C8 -15.3(3) . . . . ?
C1 S1 C10 C15 -111.3(3) . . . . ?
C1 S1 C10 C11 73.8(3) . . . . ?
C15 C10 C11 C12 0.9(6) . . . . ?
S1 C10 C11 C12 175.6(3) . . . . ?
C10 C11 C12 C13 0.0(7) . . . . ?
C11 C12 C13 C14 -0.4(8) . . . . ?
C12 C13 C14 C15 0.0(8) . . . . ?
C11 C10 C15 C14 -1.3(5) . . . . ?
S1 C10 C15 C14 -176.2(3) . . . . ?
C13 C14 C15 C10 0.9(6) . . . . ?
C9 S2 C16 C17 -72.3(3) . . . . ?
C9 S2 C16 C21 110.8(3) . . . . ?
C21 C16 C17 C18 -2.6(5) . . . . ?
S2 C16 C17 C18 -179.6(3) . . . . ?
C16 C17 C18 C19 2.3(6) . . . . ?
C17 C18 C19 C20 -0.2(6) . . . . ?
C18 C19 C20 C21 -1.6(6) . . . . ?
C17 C16 C21 C20 0.9(5) . . . . ?
S2 C16 C21 C20 177.8(3) . . . . ?
C19 C20 C21 C16 1.2(6) . . . . ?
C5 S3 C22 C23 -149.5(3) . . . . ?
C5 S3 C22 C27 35.4(3) . . . . ?
C27 C22 C23 C24 -0.9(5) . . . . ?
S3 C22 C23 C24 -176.3(3) . . . . ?
C22 C23 C24 C25 -1.4(5) . . . . ?
C23 C24 C25 C26 1.3(6) . . . . ?
C24 C25 C26 C27 1.1(6) . . . . ?
C25 C26 C27 C22 -3.4(5) . . . . ?
C23 C22 C27 C26 3.3(5) . . . . ?
S3 C22 C27 C26 178.2(3) . . . . ?

_refine_diff_density_max         0.682
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1004338'
