# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_i
_database_code_depnum_ccdc_archive 'CCDC 1517851'

_audit_update_record             
;
2016-11-17 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;
_publcif_datablock.id            {bff1a240-ce58-454f-a87e-6653bcc3d6cd}

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
10-(4-(fluoro(methyl)diphenyl-l5-stibaneyl)phenyl)-1,3,5,5,7,9-hexamethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H37 B F N2 Sb, (C H4 O)'
_chemical_formula_sum            'C35 H41 B F N2 O Sb'
_chemical_formula_weight         657.26

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'
O O 0.0106 0.0060 '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'
Sb Sb -0.5866 1.5461 '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                   12.917(3)
_cell_length_b                   23.857(4)
_cell_length_c                   10.1194(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.282(13)
_cell_angle_gamma                90
_cell_volume                     3115.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    993
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      16.16

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   0.4271
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.921
_shelx_estimated_absorpt_T_min   0.646
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      163(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27085
_diffrn_reflns_av_unetI/netI     0.1489
_diffrn_reflns_av_R_equivalents  0.1958
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.707
_diffrn_reflns_theta_max         23.988
_diffrn_reflns_theta_full        23.988
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4881
_reflns_number_gt                2792
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0582P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4881
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1327
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.001
_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
Sb1 Sb 0.03129(4) 0.60574(2) 0.03098(6) 0.0288(2) Uani 1 1 d . . . . .
O1 O -0.1994(5) 0.5030(3) 0.2861(7) 0.0526(19) Uani 1 1 d . . . . .
H1 H -0.150(7) 0.520(4) 0.221(7) 0.079 Uiso 1 1 calc R U . . .
F1 F -0.0798(3) 0.55089(19) 0.1033(4) 0.0371(12) Uani 1 1 d . . . . .
C1 C 0.3651(7) 0.9351(4) -0.1353(9) 0.039(2) Uani 1 1 d . . . . .
N2 N 0.5120(5) 0.8136(3) -0.2892(6) 0.0290(17) Uani 1 1 d . . . . .
C2 C 0.2767(7) 0.9235(4) -0.0644(9) 0.035(2) Uani 1 1 d . . . . .
H2 H 0.2365 0.9506 -0.0207 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2570(6) 0.8670(4) -0.0674(8) 0.030(2) Uani 1 1 d . . . . .
C4 C 0.3379(6) 0.8435(4) -0.1400(8) 0.030(2) Uani 1 1 d . . . . .
C5 C 0.3605(6) 0.7876(4) -0.1709(8) 0.028(2) Uani 1 1 d . . . . .
C6 C 0.4462(6) 0.7720(3) -0.2406(8) 0.027(2) Uani 1 1 d . . . . .
C7 C 0.4777(6) 0.7194(3) -0.2913(8) 0.027(2) Uani 1 1 d . . . . .
C8 C 0.5619(6) 0.7306(4) -0.3666(8) 0.032(2) Uani 1 1 d . . . . .
H8 H 0.6010 0.7034 -0.4117 0.038 Uiso 1 1 calc R U . . .
C9 C 0.5805(6) 0.7877(4) -0.3660(8) 0.031(2) Uani 1 1 d . . . . .
C10 C 0.4117(8) 0.9911(3) -0.1545(10) 0.047(3) Uani 1 1 d . . . . .
H10A H 0.3809 1.0083 -0.2347 0.071 Uiso 1 1 calc R U . . .
H10B H 0.4866 0.9871 -0.1635 0.071 Uiso 1 1 calc R U . . .
H10C H 0.3984 1.0148 -0.0780 0.071 Uiso 1 1 calc R U . . .
C11 C 0.1669(6) 0.8400(4) -0.0032(9) 0.044(3) Uani 1 1 d . . . . .
H11A H 0.1130 0.8311 -0.0708 0.066 Uiso 1 1 calc R U . . .
H11B H 0.1390 0.8657 0.0618 0.066 Uiso 1 1 calc R U . . .
H11C H 0.1901 0.8054 0.0413 0.066 Uiso 1 1 calc R U . . .
C12 C 0.4316(7) 0.6620(3) -0.2734(9) 0.043(2) Uani 1 1 d . . . . .
H12A H 0.3561 0.6642 -0.2857 0.064 Uiso 1 1 calc R U . . .
H12B H 0.4496 0.6483 -0.1841 0.064 Uiso 1 1 calc R U . . .
H12C H 0.4592 0.6362 -0.3387 0.064 Uiso 1 1 calc R U . . .
C13 C 0.6609(6) 0.8160(4) -0.4410(9) 0.039(2) Uani 1 1 d . . . . .
H13A H 0.7164 0.7894 -0.4589 0.058 Uiso 1 1 calc R U . . .
H13B H 0.6894 0.8475 -0.3892 0.058 Uiso 1 1 calc R U . . .
H13C H 0.6302 0.8300 -0.5249 0.058 Uiso 1 1 calc R U . . .
C14 C 0.4967(7) 0.9147(4) -0.3946(9) 0.039(2) Uani 1 1 d . . . . .
H14A H 0.5645 0.9157 -0.4347 0.059 Uiso 1 1 calc R U . . .
H14B H 0.4744 0.9530 -0.3759 0.059 Uiso 1 1 calc R U . . .
H14C H 0.4461 0.8969 -0.4559 0.059 Uiso 1 1 calc R U . . .
C15 C 0.6041(6) 0.8939(4) -0.1600(8) 0.038(2) Uani 1 1 d . . . . .
H15A H 0.6682 0.8844 -0.2035 0.056 Uiso 1 1 calc R U . . .
H15B H 0.6000 0.8722 -0.0780 0.056 Uiso 1 1 calc R U . . .
H15C H 0.6037 0.9340 -0.1393 0.056 Uiso 1 1 calc R U . . .
C16 C 0.2863(6) 0.7428(3) -0.1297(8) 0.025(2) Uani 1 1 d . . . . .
C17 C 0.1899(6) 0.7366(3) -0.1965(8) 0.029(2) Uani 1 1 d . . . . .
H17 H 0.1715 0.7600 -0.2698 0.035 Uiso 1 1 calc R U . . .
C18 C 0.1218(6) 0.6962(4) -0.1548(8) 0.033(2) Uani 1 1 d . . . . .
H18 H 0.0573 0.6916 -0.2020 0.040 Uiso 1 1 calc R U . . .
C19 C 0.1446(6) 0.6620(3) -0.0458(8) 0.031(2) Uani 1 1 d . . . . .
C20 C 0.2410(6) 0.6697(3) 0.0183(8) 0.028(2) Uani 1 1 d . . . . .
H20 H 0.2588 0.6474 0.0937 0.034 Uiso 1 1 calc R U . . .
C21 C 0.3115(6) 0.7085(3) -0.0242(8) 0.027(2) Uani 1 1 d . . . . .
H21 H 0.3776 0.7116 0.0197 0.033 Uiso 1 1 calc R U . . .
C22 C -0.0535(7) 0.5934(3) -0.1512(8) 0.030(2) Uani 1 1 d . . . . .
C23 C -0.1597(6) 0.6032(4) -0.1560(9) 0.036(2) Uani 1 1 d . . . . .
H23 H -0.1933 0.6144 -0.0785 0.043 Uiso 1 1 calc R U . . .
C24 C -0.2161(7) 0.5965(3) -0.2732(10) 0.043(2) Uani 1 1 d . . . . .
H24 H -0.2886 0.6035 -0.2766 0.052 Uiso 1 1 calc R U . . .
C25 C -0.1676(8) 0.5797(4) -0.3867(10) 0.040(2) Uani 1 1 d . . . . .
H25 H -0.2066 0.5754 -0.4677 0.048 Uiso 1 1 calc R U . . .
C26 C -0.0627(7) 0.5691(3) -0.3814(9) 0.037(2) Uani 1 1 d . . . . .
H26 H -0.0296 0.5563 -0.4578 0.044 Uiso 1 1 calc R U . . .
C27 C -0.0059(7) 0.5774(3) -0.2643(8) 0.030(2) Uani 1 1 d . . . . .
H27 H 0.0670 0.5718 -0.2619 0.036 Uiso 1 1 calc R U . . .
C28 C -0.0419(6) 0.6641(3) 0.1477(8) 0.026(2) Uani 1 1 d . . . . .
C29 C -0.0469(6) 0.7208(3) 0.1070(8) 0.027(2) Uani 1 1 d . . . . .
H29 H -0.0115 0.7320 0.0308 0.033 Uiso 1 1 calc R U . . .
C30 C -0.1022(6) 0.7604(4) 0.1757(8) 0.031(2) Uani 1 1 d . . . . .
H30 H -0.1055 0.7982 0.1458 0.037 Uiso 1 1 calc R U . . .
C31 C -0.1524(6) 0.7448(4) 0.2873(9) 0.036(2) Uani 1 1 d . . . . .
H31 H -0.1918 0.7714 0.3337 0.043 Uiso 1 1 calc R U . . .
C32 C -0.1450(7) 0.6895(4) 0.3322(9) 0.041(2) Uani 1 1 d . . . . .
H32 H -0.1760 0.6790 0.4120 0.049 Uiso 1 1 calc R U . . .
C33 C -0.0932(6) 0.6506(4) 0.2613(9) 0.036(2) Uani 1 1 d . . . . .
H33 H -0.0922 0.6128 0.2909 0.043 Uiso 1 1 calc R U . . .
C34 C 0.1336(7) 0.5471(3) 0.1160(8) 0.036(2) Uani 1 1 d . . . . .
H34A H 0.1373 0.5143 0.0580 0.053 Uiso 1 1 calc R U . . .
H34B H 0.1091 0.5355 0.2022 0.053 Uiso 1 1 calc R U . . .
H34C H 0.2026 0.5639 0.1276 0.053 Uiso 1 1 calc R U . . .
C35 C -0.2810(8) 0.4748(4) 0.2157(11) 0.062(3) Uani 1 1 d . . . . .
H35A H -0.3158 0.5009 0.1537 0.094 Uiso 1 1 calc R U . . .
H35B H -0.3310 0.4608 0.2782 0.094 Uiso 1 1 calc R U . . .
H35C H -0.2528 0.4433 0.1666 0.094 Uiso 1 1 calc R U . . .
N1 N 0.4035(5) 0.8869(3) -0.1805(7) 0.0329(17) Uani 1 1 d . . . . .
B1 B 0.5054(8) 0.8790(4) -0.2577(11) 0.034(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 C28 2.078(8) . ?
Sb1 C34 2.087(8) . ?
Sb1 F1 2.096(4) . ?
Sb1 C22 2.127(8) . ?
Sb1 C19 2.153(9) . ?
O1 C35 1.418(11) . ?
C1 N1 1.340(10) . ?
C1 C2 1.400(12) . ?
C1 C10 1.480(12) . ?
N2 C9 1.351(10) . ?
N2 C6 1.408(9) . ?
N2 B1 1.596(11) . ?
C2 C3 1.370(11) . ?
C3 C4 1.417(11) . ?
C3 C11 1.501(11) . ?
C4 C5 1.404(11) . ?
C4 N1 1.410(10) . ?
C5 C6 1.388(11) . ?
C5 C16 1.505(11) . ?
C6 C7 1.422(11) . ?
C7 C8 1.379(11) . ?
C7 C12 1.506(11) . ?
C8 C9 1.383(11) . ?
C9 C13 1.474(11) . ?
C14 B1 1.626(13) . ?
C15 B1 1.621(12) . ?
C16 C21 1.374(11) . ?
C16 C17 1.400(10) . ?
C17 C18 1.384(11) . ?
C18 C19 1.394(11) . ?
C19 C20 1.392(11) . ?
C20 C21 1.380(10) . ?
C22 C27 1.375(11) . ?
C22 C23 1.390(11) . ?
C23 C24 1.376(12) . ?
C24 C25 1.390(12) . ?
C25 C26 1.376(12) . ?
C26 C27 1.383(11) . ?
C28 C33 1.388(11) . ?
C28 C29 1.414(11) . ?
C29 C30 1.389(11) . ?
C30 C31 1.376(11) . ?
C31 C32 1.397(12) . ?
C32 C33 1.364(11) . ?
N1 B1 1.568(12) . ?

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
C28 Sb1 C34 120.7(3) . . ?
C28 Sb1 F1 83.5(3) . . ?
C34 Sb1 F1 82.5(3) . . ?
C28 Sb1 C22 110.8(3) . . ?
C34 Sb1 C22 124.1(3) . . ?
F1 Sb1 C22 83.1(3) . . ?
C28 Sb1 C19 96.8(3) . . ?
C34 Sb1 C19 97.9(3) . . ?
F1 Sb1 C19 179.3(3) . . ?
C22 Sb1 C19 96.2(3) . . ?
N1 C1 C2 109.0(8) . . ?
N1 C1 C10 124.8(9) . . ?
C2 C1 C10 126.1(9) . . ?
C9 N2 C6 107.2(7) . . ?
C9 N2 B1 127.2(7) . . ?
C6 N2 B1 125.6(7) . . ?
C3 C2 C1 109.7(8) . . ?
C2 C3 C4 105.1(8) . . ?
C2 C3 C11 124.0(8) . . ?
C4 C3 C11 130.8(8) . . ?
C5 C4 N1 120.1(7) . . ?
C5 C4 C3 131.0(8) . . ?
N1 C4 C3 108.9(7) . . ?
C6 C5 C4 123.0(8) . . ?
C6 C5 C16 118.7(7) . . ?
C4 C5 C16 118.2(7) . . ?
C5 C6 N2 119.6(8) . . ?
C5 C6 C7 131.7(8) . . ?
N2 C6 C7 108.2(7) . . ?
C8 C7 C6 105.7(7) . . ?
C8 C7 C12 124.5(8) . . ?
C6 C7 C12 129.7(8) . . ?
C7 C8 C9 109.2(8) . . ?
N2 C9 C8 109.6(8) . . ?
N2 C9 C13 125.2(8) . . ?
C8 C9 C13 125.1(8) . . ?
C21 C16 C17 119.4(7) . . ?
C21 C16 C5 120.3(7) . . ?
C17 C16 C5 120.3(7) . . ?
C18 C17 C16 119.3(8) . . ?
C17 C18 C19 122.2(8) . . ?
C20 C19 C18 116.6(8) . . ?
C20 C19 Sb1 121.5(6) . . ?
C18 C19 Sb1 121.7(6) . . ?
C21 C20 C19 122.2(8) . . ?
C16 C21 C20 120.2(7) . . ?
C27 C22 C23 119.4(8) . . ?
C27 C22 Sb1 121.9(6) . . ?
C23 C22 Sb1 118.7(7) . . ?
C24 C23 C22 119.9(9) . . ?
C23 C24 C25 120.3(9) . . ?
C26 C25 C24 119.8(9) . . ?
C25 C26 C27 119.7(9) . . ?
C22 C27 C26 120.8(8) . . ?
C33 C28 C29 116.5(7) . . ?
C33 C28 Sb1 123.9(6) . . ?
C29 C28 Sb1 119.4(6) . . ?
C30 C29 C28 121.6(8) . . ?
C31 C30 C29 119.6(8) . . ?
C30 C31 C32 119.7(9) . . ?
C33 C32 C31 120.0(9) . . ?
C32 C33 C28 122.5(8) . . ?
C1 N1 C4 107.2(7) . . ?
C1 N1 B1 127.0(7) . . ?
C4 N1 B1 125.7(7) . . ?
N1 B1 N2 105.6(7) . . ?
N1 B1 C15 109.0(7) . . ?
N2 B1 C15 106.7(7) . . ?
N1 B1 C14 109.4(7) . . ?
N2 B1 C14 110.1(7) . . ?
C15 B1 C14 115.5(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -1.6(10) . . . . ?
C10 C1 C2 C3 -179.7(8) . . . . ?
C1 C2 C3 C4 1.5(10) . . . . ?
C1 C2 C3 C11 -178.9(8) . . . . ?
C2 C3 C4 C5 177.4(9) . . . . ?
C11 C3 C4 C5 -2.2(15) . . . . ?
C2 C3 C4 N1 -0.8(9) . . . . ?
C11 C3 C4 N1 179.6(8) . . . . ?
N1 C4 C5 C6 0.2(12) . . . . ?
C3 C4 C5 C6 -177.8(8) . . . . ?
N1 C4 C5 C16 -178.0(7) . . . . ?
C3 C4 C5 C16 4.0(13) . . . . ?
C4 C5 C6 N2 -3.2(12) . . . . ?
C16 C5 C6 N2 175.0(7) . . . . ?
C4 C5 C6 C7 -173.7(8) . . . . ?
C16 C5 C6 C7 4.5(13) . . . . ?
C9 N2 C6 C5 -172.5(7) . . . . ?
B1 N2 C6 C5 7.6(11) . . . . ?
C9 N2 C6 C7 0.0(8) . . . . ?
B1 N2 C6 C7 -179.9(7) . . . . ?
C5 C6 C7 C8 172.3(9) . . . . ?
N2 C6 C7 C8 1.0(8) . . . . ?
C5 C6 C7 C12 -6.6(14) . . . . ?
N2 C6 C7 C12 -177.9(8) . . . . ?
C6 C7 C8 C9 -1.6(9) . . . . ?
C12 C7 C8 C9 177.4(7) . . . . ?
C6 N2 C9 C8 -1.0(9) . . . . ?
B1 N2 C9 C8 178.9(7) . . . . ?
C6 N2 C9 C13 177.3(7) . . . . ?
B1 N2 C9 C13 -2.8(12) . . . . ?
C7 C8 C9 N2 1.6(10) . . . . ?
C7 C8 C9 C13 -176.7(7) . . . . ?
C6 C5 C16 C21 76.6(10) . . . . ?
C4 C5 C16 C21 -105.1(9) . . . . ?
C6 C5 C16 C17 -105.0(9) . . . . ?
C4 C5 C16 C17 73.2(10) . . . . ?
C21 C16 C17 C18 0.1(12) . . . . ?
C5 C16 C17 C18 -178.3(7) . . . . ?
C16 C17 C18 C19 1.7(12) . . . . ?
C17 C18 C19 C20 -1.3(12) . . . . ?
C17 C18 C19 Sb1 173.0(6) . . . . ?
C18 C19 C20 C21 -0.8(12) . . . . ?
Sb1 C19 C20 C21 -175.1(6) . . . . ?
C17 C16 C21 C20 -2.1(12) . . . . ?
C5 C16 C21 C20 176.2(7) . . . . ?
C19 C20 C21 C16 2.5(12) . . . . ?
C27 C22 C23 C24 0.1(12) . . . . ?
Sb1 C22 C23 C24 178.8(6) . . . . ?
C22 C23 C24 C25 0.6(13) . . . . ?
C23 C24 C25 C26 0.6(13) . . . . ?
C24 C25 C26 C27 -2.3(13) . . . . ?
C23 C22 C27 C26 -2.0(12) . . . . ?
Sb1 C22 C27 C26 179.4(6) . . . . ?
C25 C26 C27 C22 3.1(12) . . . . ?
C33 C28 C29 C30 -1.4(11) . . . . ?
Sb1 C28 C29 C30 174.6(6) . . . . ?
C28 C29 C30 C31 1.0(12) . . . . ?
C29 C30 C31 C32 1.6(12) . . . . ?
C30 C31 C32 C33 -3.7(13) . . . . ?
C31 C32 C33 C28 3.3(13) . . . . ?
C29 C28 C33 C32 -0.8(12) . . . . ?
Sb1 C28 C33 C32 -176.6(6) . . . . ?
C2 C1 N1 C4 1.0(9) . . . . ?
C10 C1 N1 C4 179.1(8) . . . . ?
C2 C1 N1 B1 -176.1(8) . . . . ?
C10 C1 N1 B1 1.9(13) . . . . ?
C5 C4 N1 C1 -178.6(8) . . . . ?
C3 C4 N1 C1 -0.1(9) . . . . ?
C5 C4 N1 B1 -1.4(12) . . . . ?
C3 C4 N1 B1 177.1(7) . . . . ?
C1 N1 B1 N2 -178.9(7) . . . . ?
C4 N1 B1 N2 4.5(10) . . . . ?
C1 N1 B1 C15 66.8(10) . . . . ?
C4 N1 B1 C15 -109.9(8) . . . . ?
C1 N1 B1 C14 -60.4(10) . . . . ?
C4 N1 B1 C14 122.9(8) . . . . ?
C9 N2 B1 N1 172.5(7) . . . . ?
C6 N2 B1 N1 -7.6(10) . . . . ?
C9 N2 B1 C15 -71.6(10) . . . . ?
C6 N2 B1 C15 108.3(8) . . . . ?
C9 N2 B1 C14 54.5(10) . . . . ?
C6 N2 B1 C14 -125.6(8) . . . . ?

_refine_diff_density_max         0.597
_refine_diff_density_min         -1.059
_refine_diff_density_rms         0.126


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_i
_database_code_depnum_ccdc_archive 'CCDC 1517850'
_audit_update_record             
;
2016-11-17 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
10-(4-(diphenylstibaneyl)phenyl)-1,3,5,5,7,9-hexamethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H34 B N2 Sb'
_chemical_formula_sum            'C33 H34 B N2 Sb'
_chemical_formula_weight         591.18

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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   50.4025(18)
_cell_length_b                   11.0109(4)
_cell_length_c                   10.1952(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.2940(10)
_cell_angle_gamma                90.00
_cell_volume                     5612.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9025
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.16

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2416
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8239
_exptl_absorpt_correction_T_max  0.9608
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            60468
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -65
_diffrn_reflns_limit_h_max       67
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         28.33
_reflns_number_total             6964
_reflns_number_gt                4990
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0462P)²+47.3440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6964
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.086796(7) 0.32806(3) 0.73035(3) 0.03458(12) Uani 1 1 d . . .
C1 C 0.22138(9) -0.1085(5) 1.2314(5) 0.0333(11) Uani 1 1 d . . .
N2 N 0.16778(8) -0.3111(3) 1.0408(4) 0.0284(8) Uani 1 1 d . . .
C3 C 0.19495(9) 0.0460(4) 1.1488(4) 0.0275(9) Uani 1 1 d . . .
C4 C 0.18489(8) -0.0668(4) 1.0934(4) 0.0235(9) Uani 1 1 d . . .
C5 C 0.16182(8) -0.0939(4) 1.0070(4) 0.0222(9) Uani 1 1 d . . .
C6 C 0.15376(9) -0.2128(4) 0.9767(4) 0.0256(9) Uani 1 1 d . . .
C7 C 0.13152(10) -0.2593(4) 0.8907(4) 0.0320(10) Uani 1 1 d . . .
C8 C 0.13256(11) -0.3833(5) 0.9085(5) 0.0399(12) Uani 1 1 d . . .
H8 H 0.1202 -0.4401 0.8653 0.048 Uiso 1 1 calc R . .
C9 C 0.15461(11) -0.4125(4) 1.0000(5) 0.0363(11) Uani 1 1 d . . .
C10 C 0.24431(11) -0.1730(6) 1.3091(6) 0.0498(14) Uani 1 1 d . . .
H10A H 0.2489 -0.2454 1.2606 0.075 Uiso 1 1 calc R . .
H10B H 0.2393 -0.1972 1.3951 0.075 Uiso 1 1 calc R . .
H10C H 0.2598 -0.1186 1.3224 0.075 Uiso 1 1 calc R . .
C11 C 0.18381(10) 0.1715(4) 1.1299(5) 0.0337(10) Uani 1 1 d . . .
H11A H 0.1872 0.2026 1.0435 0.051 Uiso 1 1 calc R . .
H11B H 0.1924 0.2246 1.1999 0.051 Uiso 1 1 calc R . .
H11C H 0.1645 0.1695 1.1338 0.051 Uiso 1 1 calc R . .
C12 C 0.11157(10) -0.1941(5) 0.7947(5) 0.0396(12) Uani 1 1 d . . .
H12A H 0.1205 -0.1279 0.7531 0.059 Uiso 1 1 calc R . .
H12B H 0.0974 -0.1606 0.8415 0.059 Uiso 1 1 calc R . .
H12C H 0.1038 -0.2510 0.7265 0.059 Uiso 1 1 calc R . .
C13 C 0.16173(13) -0.5381(5) 1.0450(6) 0.0516(15) Uani 1 1 d . . .
H13A H 0.1524 -0.5965 0.9829 0.077 Uiso 1 1 calc R . .
H13B H 0.1564 -0.5509 1.1331 0.077 Uiso 1 1 calc R . .
H13C H 0.1811 -0.5497 1.0487 0.077 Uiso 1 1 calc R . .
C14 C 0.21786(10) -0.3458(5) 1.0207(5) 0.0398(12) Uani 1 1 d . . .
H14A H 0.2148 -0.4319 0.9994 0.060 Uiso 1 1 calc R . .
H14B H 0.2363 -0.3346 1.0632 0.060 Uiso 1 1 calc R . .
H14C H 0.2151 -0.2977 0.9393 0.060 Uiso 1 1 calc R . .
C15 C 0.19862(11) -0.3745(5) 1.2600(5) 0.0403(12) Uani 1 1 d . . .
H15A H 0.1886 -0.4506 1.2465 0.060 Uiso 1 1 calc R . .
H15B H 0.1909 -0.3243 1.3248 0.060 Uiso 1 1 calc R . .
H15C H 0.2173 -0.3925 1.2928 0.060 Uiso 1 1 calc R . .
C16 C 0.14454(8) 0.0078(4) 0.9501(4) 0.0199(8) Uani 1 1 d . . .
C17 C 0.11937(8) 0.0253(4) 0.9885(4) 0.0230(9) Uani 1 1 d . . .
H17 H 0.1134 -0.0257 1.0540 0.028 Uiso 1 1 calc R . .
C18 C 0.10286(8) 0.1167(4) 0.9317(4) 0.0250(9) Uani 1 1 d . . .
H18 H 0.0857 0.1279 0.9586 0.030 Uiso 1 1 calc R . .
C19 C 0.11130(8) 0.1924(4) 0.8353(4) 0.0249(9) Uani 1 1 d . . .
C20 C 0.13672(8) 0.1758(4) 0.8004(4) 0.0244(9) Uani 1 1 d . . .
H20 H 0.1429 0.2278 0.7363 0.029 Uiso 1 1 calc R . .
C21 C 0.15328(8) 0.0848(4) 0.8573(4) 0.0229(9) Uani 1 1 d . . .
H21 H 0.1707 0.0751 0.8325 0.027 Uiso 1 1 calc R . .
C22 C 0.05872(10) 0.3429(5) 0.8733(5) 0.0406(13) Uani 1 1 d . . .
C23 C 0.06694(12) 0.3836(5) 0.9978(5) 0.0454(13) Uani 1 1 d . . .
H23 H 0.0852 0.4046 1.0216 0.054 Uiso 1 1 calc R . .
C24 C 0.04930(13) 0.3951(5) 1.0908(6) 0.0473(14) Uani 1 1 d . . .
H24 H 0.0557 0.4232 1.1772 0.057 Uiso 1 1 calc R . .
C25 C 0.02340(13) 0.3672(8) 1.0604(6) 0.078(2) Uani 1 1 d . . .
H25 H 0.0110 0.3811 1.1217 0.094 Uiso 1 1 calc R . .
C26 C 0.01526(15) 0.3183(17) 0.9396(8) 0.200(9) Uani 1 1 d . . .
H26 H -0.0027 0.2909 0.9193 0.239 Uiso 1 1 calc R . .
C27 C 0.03260(13) 0.3078(14) 0.8463(7) 0.165(7) Uani 1 1 d . . .
H27 H 0.0263 0.2757 0.7616 0.198 Uiso 1 1 calc R . .
C28 C 0.06310(9) 0.2068(5) 0.5979(5) 0.0391(13) Uani 1 1 d . . .
C29 C 0.05750(10) 0.0880(6) 0.6320(5) 0.0456(14) Uani 1 1 d . . .
H29 H 0.0645 0.0581 0.7167 0.055 Uiso 1 1 calc R . .
C30 C 0.04205(10) 0.0131(7) 0.5457(5) 0.0528(16) Uani 1 1 d . . .
H30 H 0.0384 -0.0678 0.5707 0.063 Uiso 1 1 calc R . .
C31 C 0.03171(11) 0.0565(8) 0.4214(6) 0.062(2) Uani 1 1 d . . .
H31 H 0.0209 0.0054 0.3616 0.074 Uiso 1 1 calc R . .
C32 C 0.03712(15) 0.1714(8) 0.3856(6) 0.072(2) Uani 1 1 d . . .
H32 H 0.0302 0.2004 0.3004 0.086 Uiso 1 1 calc R . .
C33 C 0.05277(12) 0.2472(7) 0.4729(5) 0.0565(17) Uani 1 1 d . . .
H33 H 0.0564 0.3276 0.4467 0.068 Uiso 1 1 calc R . .
C2 C 0.21756(9) 0.0166(4) 1.2331(5) 0.0336(11) Uani 1 1 d . . .
H2 H 0.2288 0.0729 1.2843 0.040 Uiso 1 1 calc R . .
N1 N 0.20160(7) -0.1609(3) 1.1495(4) 0.0273(8) Uani 1 1 d . . .
B1 B 0.19712(11) -0.3017(5) 1.1205(6) 0.0330(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 C19 2.137(4) . ?
Sb1 C28 2.150(6) . ?
Sb1 C22 2.163(5) . ?
C1 N1 1.346(6) . ?
C1 C2 1.392(7) . ?
C1 C10 1.495(6) . ?
N2 C9 1.338(6) . ?
N2 C6 1.407(6) . ?
N2 B1 1.598(7) . ?
C3 C2 1.376(6) . ?
C3 C4 1.430(6) . ?
C3 C11 1.495(6) . ?
C4 C5 1.399(6) . ?
C4 N1 1.410(5) . ?
C5 C6 1.394(6) . ?
C5 C16 1.491(6) . ?
C6 C7 1.427(6) . ?
C7 C8 1.378(7) . ?
C7 C12 1.495(7) . ?
C8 C9 1.395(8) . ?
C9 C13 1.486(7) . ?
C14 B1 1.623(7) . ?
C15 B1 1.626(7) . ?
C16 C21 1.383(6) . ?
C16 C17 1.388(6) . ?
C17 C18 1.385(6) . ?
C18 C19 1.396(6) . ?
C19 C20 1.385(6) . ?
C20 C21 1.384(6) . ?
C22 C23 1.360(7) . ?
C22 C27 1.366(10) . ?
C23 C24 1.386(7) . ?
C24 C25 1.338(9) . ?
C25 C26 1.359(11) . ?
C26 C27 1.376(11) . ?
C28 C33 1.387(7) . ?
C28 C29 1.392(8) . ?
C29 C30 1.374(8) . ?
C30 C31 1.393(9) . ?
C31 C32 1.354(10) . ?
C32 C33 1.391(10) . ?
N1 B1 1.589(7) . ?

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
C19 Sb1 C28 96.89(18) . . ?
C19 Sb1 C22 95.81(17) . . ?
C28 Sb1 C22 96.4(2) . . ?
N1 C1 C2 109.8(4) . . ?
N1 C1 C10 126.0(5) . . ?
C2 C1 C10 124.2(5) . . ?
C9 N2 C6 107.3(4) . . ?
C9 N2 B1 127.1(4) . . ?
C6 N2 B1 124.3(4) . . ?
C2 C3 C4 105.5(4) . . ?
C2 C3 C11 124.5(4) . . ?
C4 C3 C11 130.0(4) . . ?
C5 C4 N1 120.3(4) . . ?
C5 C4 C3 131.2(4) . . ?
N1 C4 C3 108.3(4) . . ?
C6 C5 C4 122.4(4) . . ?
C6 C5 C16 118.7(4) . . ?
C4 C5 C16 118.8(4) . . ?
C5 C6 N2 120.3(4) . . ?
C5 C6 C7 131.0(4) . . ?
N2 C6 C7 108.6(4) . . ?
C8 C7 C6 105.1(4) . . ?
C8 C7 C12 125.0(4) . . ?
C6 C7 C12 129.9(4) . . ?
C7 C8 C9 109.3(4) . . ?
N2 C9 C8 109.7(4) . . ?
N2 C9 C13 126.1(5) . . ?
C8 C9 C13 124.2(5) . . ?
C21 C16 C17 119.3(4) . . ?
C21 C16 C5 120.4(4) . . ?
C17 C16 C5 120.3(4) . . ?
C18 C17 C16 120.4(4) . . ?
C17 C18 C19 120.5(4) . . ?
C20 C19 C18 118.5(4) . . ?
C20 C19 Sb1 117.3(3) . . ?
C18 C19 Sb1 124.2(3) . . ?
C21 C20 C19 121.1(4) . . ?
C16 C21 C20 120.2(4) . . ?
C23 C22 C27 116.9(5) . . ?
C23 C22 Sb1 120.4(4) . . ?
C27 C22 Sb1 122.6(4) . . ?
C22 C23 C24 121.5(5) . . ?
C25 C24 C23 120.8(6) . . ?
C24 C25 C26 118.3(6) . . ?
C25 C26 C27 121.0(8) . . ?
C22 C27 C26 121.2(7) . . ?
C33 C28 C29 117.8(6) . . ?
C33 C28 Sb1 119.5(5) . . ?
C29 C28 Sb1 122.8(4) . . ?
C30 C29 C28 121.4(5) . . ?
C29 C30 C31 119.5(7) . . ?
C32 C31 C30 120.1(6) . . ?
C31 C32 C33 120.4(6) . . ?
C28 C33 C32 120.8(7) . . ?
C3 C2 C1 109.3(4) . . ?
C1 N1 C4 107.1(4) . . ?
C1 N1 B1 127.6(4) . . ?
C4 N1 B1 125.3(4) . . ?
N1 B1 N2 105.0(4) . . ?
N1 B1 C14 108.7(4) . . ?
N2 B1 C14 106.9(4) . . ?
N1 B1 C15 109.2(4) . . ?
N2 B1 C15 110.5(4) . . ?
C14 B1 C15 116.0(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 176.5(5) . . . . ?
C11 C3 C4 C5 -0.6(8) . . . . ?
C2 C3 C4 N1 1.5(5) . . . . ?
C11 C3 C4 N1 -175.7(5) . . . . ?
N1 C4 C5 C6 2.7(6) . . . . ?
C3 C4 C5 C6 -171.9(4) . . . . ?
N1 C4 C5 C16 179.7(4) . . . . ?
C3 C4 C5 C16 5.1(7) . . . . ?
C4 C5 C6 N2 4.7(6) . . . . ?
C16 C5 C6 N2 -172.3(4) . . . . ?
C4 C5 C6 C7 -178.8(4) . . . . ?
C16 C5 C6 C7 4.2(7) . . . . ?
C9 N2 C6 C5 175.6(4) . . . . ?
B1 N2 C6 C5 -16.6(6) . . . . ?
C9 N2 C6 C7 -1.7(5) . . . . ?
B1 N2 C6 C7 166.1(4) . . . . ?
C5 C6 C7 C8 -175.4(5) . . . . ?
N2 C6 C7 C8 1.5(5) . . . . ?
C5 C6 C7 C12 7.5(8) . . . . ?
N2 C6 C7 C12 -175.6(5) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C12 C7 C8 C9 176.5(5) . . . . ?
C6 N2 C9 C8 1.2(5) . . . . ?
B1 N2 C9 C8 -166.1(4) . . . . ?
C6 N2 C9 C13 -178.0(5) . . . . ?
B1 N2 C9 C13 14.6(8) . . . . ?
C7 C8 C9 N2 -0.3(6) . . . . ?
C7 C8 C9 C13 179.0(5) . . . . ?
C6 C5 C16 C21 -112.6(5) . . . . ?
C4 C5 C16 C21 70.3(5) . . . . ?
C6 C5 C16 C17 66.5(5) . . . . ?
C4 C5 C16 C17 -110.6(5) . . . . ?
C21 C16 C17 C18 1.8(6) . . . . ?
C5 C16 C17 C18 -177.3(4) . . . . ?
C16 C17 C18 C19 0.0(6) . . . . ?
C17 C18 C19 C20 -1.6(6) . . . . ?
C17 C18 C19 Sb1 175.4(3) . . . . ?
C28 Sb1 C19 C20 100.5(4) . . . . ?
C22 Sb1 C19 C20 -162.4(4) . . . . ?
C28 Sb1 C19 C18 -76.6(4) . . . . ?
C22 Sb1 C19 C18 20.6(4) . . . . ?
C18 C19 C20 C21 1.4(6) . . . . ?
Sb1 C19 C20 C21 -175.8(3) . . . . ?
C17 C16 C21 C20 -2.0(6) . . . . ?
C5 C16 C21 C20 177.1(4) . . . . ?
C19 C20 C21 C16 0.4(6) . . . . ?
C19 Sb1 C22 C23 64.0(5) . . . . ?
C28 Sb1 C22 C23 161.6(5) . . . . ?
C19 Sb1 C22 C27 -113.2(8) . . . . ?
C28 Sb1 C22 C27 -15.6(9) . . . . ?
C27 C22 C23 C24 -3.3(11) . . . . ?
Sb1 C22 C23 C24 179.3(4) . . . . ?
C22 C23 C24 C25 -0.5(10) . . . . ?
C23 C24 C25 C26 5.1(14) . . . . ?
C24 C25 C26 C27 -6(2) . . . . ?
C23 C22 C27 C26 2.6(18) . . . . ?
Sb1 C22 C27 C26 179.9(12) . . . . ?
C25 C26 C27 C22 2(2) . . . . ?
C19 Sb1 C28 C33 -150.3(4) . . . . ?
C22 Sb1 C28 C33 113.1(4) . . . . ?
C19 Sb1 C28 C29 29.8(4) . . . . ?
C22 Sb1 C28 C29 -66.9(4) . . . . ?
C33 C28 C29 C30 -0.6(8) . . . . ?
Sb1 C28 C29 C30 179.3(4) . . . . ?
C28 C29 C30 C31 0.0(8) . . . . ?
C29 C30 C31 C32 0.7(9) . . . . ?
C30 C31 C32 C33 -0.6(10) . . . . ?
C29 C28 C33 C32 0.7(8) . . . . ?
Sb1 C28 C33 C32 -179.3(5) . . . . ?
C31 C32 C33 C28 0.0(10) . . . . ?
C4 C3 C2 C1 -0.4(6) . . . . ?
C11 C3 C2 C1 176.9(5) . . . . ?
N1 C1 C2 C3 -0.8(6) . . . . ?
C10 C1 C2 C3 178.7(5) . . . . ?
C2 C1 N1 C4 1.7(5) . . . . ?
C10 C1 N1 C4 -177.8(5) . . . . ?
C2 C1 N1 B1 -177.6(4) . . . . ?
C10 C1 N1 B1 2.9(8) . . . . ?
C5 C4 N1 C1 -177.6(4) . . . . ?
C3 C4 N1 C1 -2.0(5) . . . . ?
C5 C4 N1 B1 1.7(6) . . . . ?
C3 C4 N1 B1 177.3(4) . . . . ?
C1 N1 B1 N2 168.5(4) . . . . ?
C4 N1 B1 N2 -10.6(6) . . . . ?
C1 N1 B1 C14 -77.4(6) . . . . ?
C4 N1 B1 C14 103.4(5) . . . . ?
C1 N1 B1 C15 50.1(6) . . . . ?
C4 N1 B1 C15 -129.1(4) . . . . ?
C9 N2 B1 N1 -176.6(4) . . . . ?
C6 N2 B1 N1 18.0(6) . . . . ?
C9 N2 B1 C14 68.0(6) . . . . ?
C6 N2 B1 C14 -97.4(5) . . . . ?
C9 N2 B1 C15 -59.0(6) . . . . ?
C6 N2 B1 C15 135.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.498
_refine_diff_density_min         -2.439
_refine_diff_density_rms         0.127
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, diethyl ether'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_i
_database_code_depnum_ccdc_archive 'CCDC 1517852'

_audit_update_record             
;
2016-11-17 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;
_publcif_datablock.id            {efbdf6b2-119f-4a81-bcbf-d4a2449fae7b}

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"[(4-(1,3,5,5,7,9-hexamethyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-10-yl)phenyl)(methyl)diphenylantimony(V)]trifluoromethanesulfonate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H37 B N2 Sb, (C F3 O3 S)'
_chemical_formula_sum            'C35 H37 B F3 N2 O3 S Sb'
_chemical_formula_weight         755.29

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'
O O 0.0106 0.0060 '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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.6694(6)
_cell_length_b                   24.9626(12)
_cell_length_c                   10.0894(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.504(2)
_cell_angle_gamma                90.00
_cell_volume                     3432.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.36

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7276
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_process_details   sadabs

_exptl_special_details           ?

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            99924
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         26.42
_reflns_number_total             7050
_reflns_number_gt                5899
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0296P)²+9.5750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7050
_refine_ls_number_parameters     422
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.480193(17) 0.384442(9) 0.97242(2) 0.01689(8) Uani 1 1 d . . .
O1 O 0.3870(2) 0.53434(11) 0.1018(3) 0.0293(6) Uani 1 1 d . . .
F1 F 0.1913(2) 0.55972(13) 0.1557(4) 0.0774(11) Uani 1 1 d . . .
C1 C -0.0387(3) 0.22038(18) 1.3396(4) 0.0311(9) Uani 1 1 d . . .
N1 N 0.0238(2) 0.19346(13) 1.2676(3) 0.0242(7) Uani 1 1 d . . .
B1 B 0.0242(3) 0.13066(18) 1.2381(5) 0.0282(10) Uani 1 1 d . . .
C3 C 0.0638(3) 0.28307(16) 1.2667(4) 0.0243(8) Uani 1 1 d . . .
O3 O 0.3525(3) 0.50663(13) 0.3232(3) 0.0459(8) Uani 1 1 d . . .
F3 F 0.1896(2) 0.49767(14) 0.0094(4) 0.0676(10) Uani 1 1 d . . .
C4 C 0.0898(3) 0.23117(15) 1.2203(4) 0.0213(8) Uani 1 1 d . . .
C5 C 0.1692(3) 0.21411(14) 1.1529(3) 0.0193(7) Uani 1 1 d . . .
C6 C 0.1856(3) 0.16024(15) 1.1245(4) 0.0220(8) Uani 1 1 d . . .
C7 C 0.2596(3) 0.13424(17) 1.0545(4) 0.0285(9) Uani 1 1 d . . .
C8 C 0.2358(3) 0.08049(17) 1.0529(4) 0.0363(11) Uani 1 1 d . . .
H8 H 0.2712 0.0530 1.0126 0.044 Uiso 1 1 calc R . .
C9 C 0.1518(3) 0.07300(17) 1.1197(4) 0.0337(10) Uani 1 1 d . . .
C10 C -0.1183(3) 0.1960(2) 1.4157(5) 0.0417(12) Uani 1 1 d . . .
H10A H -0.1692 0.2229 1.4274 0.063 Uiso 1 1 calc R . .
H10B H -0.0901 0.1840 1.5029 0.063 Uiso 1 1 calc R . .
H10C H -0.1472 0.1654 1.3661 0.063 Uiso 1 1 calc R . .
C11 C 0.1103(3) 0.33679(16) 1.2491(4) 0.0303(9) Uani 1 1 d . . .
H11A H 0.0952 0.3491 1.1576 0.045 Uiso 1 1 calc R . .
H11B H 0.1815 0.3338 1.2674 0.045 Uiso 1 1 calc R . .
H11C H 0.0844 0.3625 1.3109 0.045 Uiso 1 1 calc R . .
C12 C 0.3444(3) 0.15790(19) 0.9908(4) 0.0381(11) Uani 1 1 d . . .
H12A H 0.3681 0.1323 0.9270 0.057 Uiso 1 1 calc R . .
H12B H 0.3973 0.1660 1.0592 0.057 Uiso 1 1 calc R . .
H12C H 0.3237 0.1910 0.9444 0.057 Uiso 1 1 calc R . .
C13 C 0.1040(4) 0.01990(18) 1.1414(6) 0.0500(13) Uani 1 1 d . . .
H13A H 0.0331 0.0250 1.1442 0.075 Uiso 1 1 calc R . .
H13B H 0.1312 0.0045 1.2257 0.075 Uiso 1 1 calc R . .
H13C H 0.1166 -0.0044 1.0684 0.075 Uiso 1 1 calc R . .
C14 C 0.0331(3) 0.09787(18) 1.3770(4) 0.0359(10) Uani 1 1 d . . .
H14A H 0.0309 0.0593 1.3586 0.054 Uiso 1 1 calc R . .
H14B H -0.0215 0.1077 1.4296 0.054 Uiso 1 1 calc R . .
H14C H 0.0954 0.1068 1.4269 0.054 Uiso 1 1 calc R . .
C15 C -0.0716(3) 0.1183(2) 1.1348(5) 0.0398(11) Uani 1 1 d . . .
H15A H -0.0602 0.1325 1.0468 0.060 Uiso 1 1 calc R . .
H15B H -0.1296 0.1355 1.1671 0.060 Uiso 1 1 calc R . .
H15C H -0.0822 0.0795 1.1288 0.060 Uiso 1 1 calc R . .
C16 C 0.2414(3) 0.25484(14) 1.1137(3) 0.0183(7) Uani 1 1 d . . .
C17 C 0.2166(3) 0.28922(14) 1.0084(3) 0.0190(7) Uani 1 1 d . . .
H17 H 0.1532 0.2872 0.9627 0.023 Uiso 1 1 calc R . .
C18 C 0.2837(3) 0.32655(14) 0.9692(4) 0.0194(7) Uani 1 1 d . . .
H18 H 0.2666 0.3496 0.8961 0.023 Uiso 1 1 calc R . .
C19 C 0.3760(2) 0.33022(14) 1.0373(3) 0.0176(7) Uani 1 1 d . . .
C20 C 0.4004(3) 0.29637(15) 1.1446(3) 0.0203(8) Uani 1 1 d . . .
H20 H 0.4630 0.2992 1.1921 0.024 Uiso 1 1 calc R . .
C21 C 0.3336(3) 0.25872(15) 1.1823(4) 0.0211(8) Uani 1 1 d . . .
H21 H 0.3507 0.2355 1.2550 0.025 Uiso 1 1 calc R . .
C22 C 0.5850(3) 0.39550(13) 1.1359(3) 0.0185(7) Uani 1 1 d . . .
C23 C 0.6824(3) 0.38502(16) 1.1146(4) 0.0280(8) Uani 1 1 d . . .
H23 H 0.6999 0.3755 1.0284 0.034 Uiso 1 1 calc R . .
C24 C 0.7540(3) 0.38858(18) 1.2197(5) 0.0408(11) Uani 1 1 d . . .
H24 H 0.8205 0.3812 1.2053 0.049 Uiso 1 1 calc R . .
C25 C 0.7293(4) 0.40270(18) 1.3445(5) 0.0430(13) Uani 1 1 d . . .
H25 H 0.7788 0.4050 1.4159 0.052 Uiso 1 1 calc R . .
C26 C 0.6328(4) 0.41355(17) 1.3664(4) 0.0390(11) Uani 1 1 d . . .
H26 H 0.6161 0.4239 1.4524 0.047 Uiso 1 1 calc R . .
C27 C 0.5593(3) 0.40926(15) 1.2615(4) 0.0285(9) Uani 1 1 d . . .
H27 H 0.4926 0.4157 1.2765 0.034 Uiso 1 1 calc R . .
C28 C 0.5581(3) 0.33457(14) 0.8463(3) 0.0184(7) Uani 1 1 d . . .
C29 C 0.5992(3) 0.35389(15) 0.7341(4) 0.0236(8) Uani 1 1 d . . .
H29 H 0.5896 0.3902 0.7081 0.028 Uiso 1 1 calc R . .
C30 C 0.6542(3) 0.32012(16) 0.6600(4) 0.0267(8) Uani 1 1 d . . .
H30 H 0.6814 0.3333 0.5826 0.032 Uiso 1 1 calc R . .
C31 C 0.6697(3) 0.26724(16) 0.6980(4) 0.0259(8) Uani 1 1 d . . .
H31 H 0.7084 0.2445 0.6475 0.031 Uiso 1 1 calc R . .
C32 C 0.6289(3) 0.24746(15) 0.8097(4) 0.0236(8) Uani 1 1 d . . .
H32 H 0.6393 0.2112 0.8355 0.028 Uiso 1 1 calc R . .
C33 C 0.5728(3) 0.28083(14) 0.8835(4) 0.0207(8) Uani 1 1 d . . .
H33 H 0.5442 0.2672 0.9595 0.025 Uiso 1 1 calc R . .
C34 C 0.4040(3) 0.44328(15) 0.8552(4) 0.0246(8) Uani 1 1 d . . .
H34A H 0.4296 0.4444 0.7672 0.037 Uiso 1 1 calc R . .
H34B H 0.4131 0.4783 0.8983 0.037 Uiso 1 1 calc R . .
H34C H 0.3340 0.4344 0.8457 0.037 Uiso 1 1 calc R . .
C35 C 0.2116(3) 0.5079(2) 0.1373(6) 0.0455(12) Uani 1 1 d . . .
S2 S 0.34063(7) 0.49604(4) 0.18273(9) 0.0225(2) Uani 1 1 d . . .
N2 N 0.1200(2) 0.12051(13) 1.1633(3) 0.0273(7) Uani 1 1 d . . .
O2 O 0.3539(2) 0.44097(11) 0.1439(3) 0.0352(7) Uani 1 1 d . . .
F2 F 0.1542(2) 0.47883(16) 0.2067(4) 0.0800(11) Uani 1 1 d . . .
C2 C -0.0165(3) 0.27477(18) 1.3392(4) 0.0302(9) Uani 1 1 d . . .
H2 H -0.0512 0.3019 1.3820 0.036 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 C19 2.106(3) . ?
Sb1 C34 2.109(3) . ?
Sb1 C22 2.117(3) . ?
Sb1 C28 2.125(4) . ?
O1 S2 1.437(3) . ?
F1 C35 1.340(6) . ?
C1 N1 1.344(5) . ?
C1 C2 1.391(6) . ?
C1 C10 1.508(6) . ?
N1 C4 1.412(5) . ?
N1 B1 1.596(6) . ?
B1 N2 1.583(6) . ?
B1 C14 1.619(6) . ?
B1 C15 1.637(6) . ?
C3 C2 1.381(6) . ?
C3 C4 1.432(5) . ?
C3 C11 1.501(6) . ?
O3 S2 1.439(3) . ?
F3 C35 1.327(6) . ?
C4 C5 1.393(5) . ?
C5 C6 1.397(5) . ?
C5 C16 1.491(5) . ?
C6 N2 1.413(5) . ?
C6 C7 1.434(6) . ?
C7 C8 1.381(6) . ?
C7 C12 1.491(6) . ?
C8 C9 1.388(7) . ?
C9 N2 1.349(5) . ?
C9 C13 1.502(6) . ?
C16 C17 1.387(5) . ?
C16 C21 1.393(5) . ?
C17 C18 1.386(5) . ?
C18 C19 1.392(5) . ?
C19 C20 1.393(5) . ?
C20 C21 1.384(5) . ?
C22 C27 1.384(5) . ?
C22 C23 1.390(6) . ?
C23 C24 1.388(6) . ?
C24 C25 1.376(7) . ?
C25 C26 1.382(7) . ?
C26 C27 1.405(6) . ?
C28 C29 1.389(5) . ?
C28 C33 1.403(5) . ?
C29 C30 1.387(5) . ?
C30 C31 1.386(5) . ?
C31 C32 1.386(6) . ?
C32 C33 1.388(5) . ?
C35 F2 1.310(6) . ?
C35 S2 1.812(5) . ?
S2 O2 1.445(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
C19 Sb1 C34 107.81(14) . . ?
C19 Sb1 C22 105.94(13) . . ?
C34 Sb1 C22 128.35(14) . . ?
C19 Sb1 C28 101.10(13) . . ?
C34 Sb1 C28 108.71(14) . . ?
C22 Sb1 C28 101.68(14) . . ?
N1 C1 C2 109.8(4) . . ?
N1 C1 C10 126.0(4) . . ?
C2 C1 C10 124.1(4) . . ?
C1 N1 C4 107.4(3) . . ?
C1 N1 B1 127.1(3) . . ?
C4 N1 B1 125.5(3) . . ?
N2 B1 N1 105.1(3) . . ?
N2 B1 C14 108.8(3) . . ?
N1 B1 C14 109.7(3) . . ?
N2 B1 C15 108.4(3) . . ?
N1 B1 C15 106.9(3) . . ?
C14 B1 C15 117.3(3) . . ?
C2 C3 C4 105.4(4) . . ?
C2 C3 C11 123.9(4) . . ?
C4 C3 C11 130.7(4) . . ?
C5 C4 N1 120.3(3) . . ?
C5 C4 C3 131.3(3) . . ?
N1 C4 C3 108.1(3) . . ?
C4 C5 C6 122.5(3) . . ?
C4 C5 C16 118.6(3) . . ?
C6 C5 C16 118.8(3) . . ?
C5 C6 N2 120.3(3) . . ?
C5 C6 C7 131.9(4) . . ?
N2 C6 C7 107.9(3) . . ?
C8 C7 C6 105.7(4) . . ?
C8 C7 C12 124.8(4) . . ?
C6 C7 C12 129.5(4) . . ?
C7 C8 C9 109.2(4) . . ?
N2 C9 C8 109.9(4) . . ?
N2 C9 C13 125.0(4) . . ?
C8 C9 C13 125.1(4) . . ?
C17 C16 C21 119.7(3) . . ?
C17 C16 C5 119.9(3) . . ?
C21 C16 C5 120.5(3) . . ?
C18 C17 C16 120.4(3) . . ?
C17 C18 C19 119.9(3) . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 Sb1 119.9(3) . . ?
C20 C19 Sb1 120.3(3) . . ?
C21 C20 C19 120.2(3) . . ?
C20 C21 C16 120.1(3) . . ?
C27 C22 C23 120.3(3) . . ?
C27 C22 Sb1 122.7(3) . . ?
C23 C22 Sb1 116.9(3) . . ?
C24 C23 C22 119.7(4) . . ?
C25 C24 C23 120.5(4) . . ?
C24 C25 C26 120.2(4) . . ?
C25 C26 C27 120.0(4) . . ?
C22 C27 C26 119.4(4) . . ?
C29 C28 C33 119.4(3) . . ?
C29 C28 Sb1 122.6(3) . . ?
C33 C28 Sb1 117.9(3) . . ?
C30 C29 C28 119.9(3) . . ?
C31 C30 C29 120.5(4) . . ?
C30 C31 C32 120.1(4) . . ?
C31 C32 C33 119.8(3) . . ?
C32 C33 C28 120.2(3) . . ?
F2 C35 F3 108.3(4) . . ?
F2 C35 F1 108.8(4) . . ?
F3 C35 F1 106.6(5) . . ?
F2 C35 S2 112.7(4) . . ?
F3 C35 S2 110.9(3) . . ?
F1 C35 S2 109.3(3) . . ?
O1 S2 O3 114.66(18) . . ?
O1 S2 O2 114.11(17) . . ?
O3 S2 O2 115.81(19) . . ?
O1 S2 C35 102.3(2) . . ?
O3 S2 C35 104.5(2) . . ?
O2 S2 C35 103.1(2) . . ?
C9 N2 C6 107.4(4) . . ?
C9 N2 B1 126.6(4) . . ?
C6 N2 B1 125.9(3) . . ?
C3 C2 C1 109.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C4 0.9(4) . . . . ?
C10 C1 N1 C4 -176.4(4) . . . . ?
C2 C1 N1 B1 -178.4(3) . . . . ?
C10 C1 N1 B1 4.4(6) . . . . ?
C1 N1 B1 N2 -173.8(3) . . . . ?
C4 N1 B1 N2 7.1(5) . . . . ?
C1 N1 B1 C14 -57.0(5) . . . . ?
C4 N1 B1 C14 123.9(4) . . . . ?
C1 N1 B1 C15 71.1(5) . . . . ?
C4 N1 B1 C15 -108.0(4) . . . . ?
C1 N1 C4 C5 173.8(3) . . . . ?
B1 N1 C4 C5 -6.9(5) . . . . ?
C1 N1 C4 C3 -0.4(4) . . . . ?
B1 N1 C4 C3 178.9(3) . . . . ?
C2 C3 C4 C5 -173.6(4) . . . . ?
C11 C3 C4 C5 4.9(7) . . . . ?
C2 C3 C4 N1 -0.3(4) . . . . ?
C11 C3 C4 N1 178.2(4) . . . . ?
N1 C4 C5 C6 2.5(5) . . . . ?
C3 C4 C5 C6 175.1(4) . . . . ?
N1 C4 C5 C16 -175.4(3) . . . . ?
C3 C4 C5 C16 -2.8(6) . . . . ?
C4 C5 C6 N2 0.5(5) . . . . ?
C16 C5 C6 N2 178.4(3) . . . . ?
C4 C5 C6 C7 178.1(4) . . . . ?
C16 C5 C6 C7 -4.0(6) . . . . ?
C5 C6 C7 C8 -177.4(4) . . . . ?
N2 C6 C7 C8 0.4(4) . . . . ?
C5 C6 C7 C12 0.8(7) . . . . ?
N2 C6 C7 C12 178.7(4) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C12 C7 C8 C9 -179.0(4) . . . . ?
C7 C8 C9 N2 0.6(5) . . . . ?
C7 C8 C9 C13 -178.8(4) . . . . ?
C4 C5 C16 C17 -74.3(4) . . . . ?
C6 C5 C16 C17 107.7(4) . . . . ?
C4 C5 C16 C21 105.6(4) . . . . ?
C6 C5 C16 C21 -72.4(4) . . . . ?
C21 C16 C17 C18 1.4(5) . . . . ?
C5 C16 C17 C18 -178.7(3) . . . . ?
C16 C17 C18 C19 -1.0(5) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C17 C18 C19 Sb1 177.2(3) . . . . ?
C34 Sb1 C19 C18 20.7(3) . . . . ?
C22 Sb1 C19 C18 161.0(3) . . . . ?
C28 Sb1 C19 C18 -93.3(3) . . . . ?
C34 Sb1 C19 C20 -161.9(3) . . . . ?
C22 Sb1 C19 C20 -21.6(3) . . . . ?
C28 Sb1 C19 C20 84.1(3) . . . . ?
C18 C19 C20 C21 1.0(5) . . . . ?
Sb1 C19 C20 C21 -176.4(3) . . . . ?
C19 C20 C21 C16 -0.6(6) . . . . ?
C17 C16 C21 C20 -0.6(5) . . . . ?
C5 C16 C21 C20 179.5(3) . . . . ?
C19 Sb1 C22 C27 -51.9(3) . . . . ?
C34 Sb1 C22 C27 77.3(3) . . . . ?
C28 Sb1 C22 C27 -157.1(3) . . . . ?
C19 Sb1 C22 C23 124.2(3) . . . . ?
C34 Sb1 C22 C23 -106.6(3) . . . . ?
C28 Sb1 C22 C23 18.9(3) . . . . ?
C27 C22 C23 C24 -0.2(6) . . . . ?
Sb1 C22 C23 C24 -176.4(3) . . . . ?
C22 C23 C24 C25 -0.4(6) . . . . ?
C23 C24 C25 C26 -0.1(7) . . . . ?
C24 C25 C26 C27 1.1(6) . . . . ?
C23 C22 C27 C26 1.2(5) . . . . ?
Sb1 C22 C27 C26 177.2(3) . . . . ?
C25 C26 C27 C22 -1.7(6) . . . . ?
C19 Sb1 C28 C29 147.7(3) . . . . ?
C34 Sb1 C28 C29 34.4(3) . . . . ?
C22 Sb1 C28 C29 -103.2(3) . . . . ?
C19 Sb1 C28 C33 -36.0(3) . . . . ?
C34 Sb1 C28 C33 -149.3(3) . . . . ?
C22 Sb1 C28 C33 73.1(3) . . . . ?
C33 C28 C29 C30 -0.1(5) . . . . ?
Sb1 C28 C29 C30 176.2(3) . . . . ?
C28 C29 C30 C31 -0.8(6) . . . . ?
C29 C30 C31 C32 1.0(6) . . . . ?
C30 C31 C32 C33 -0.3(6) . . . . ?
C31 C32 C33 C28 -0.7(5) . . . . ?
C29 C28 C33 C32 0.8(5) . . . . ?
Sb1 C28 C33 C32 -175.6(3) . . . . ?
F2 C35 S2 O1 -176.1(4) . . . . ?
F3 C35 S2 O1 62.3(4) . . . . ?
F1 C35 S2 O1 -55.0(4) . . . . ?
F2 C35 S2 O3 -56.2(4) . . . . ?
F3 C35 S2 O3 -177.9(3) . . . . ?
F1 C35 S2 O3 64.9(4) . . . . ?
F2 C35 S2 O2 65.3(4) . . . . ?
F3 C35 S2 O2 -56.4(4) . . . . ?
F1 C35 S2 O2 -173.7(4) . . . . ?
C8 C9 N2 C6 -0.3(4) . . . . ?
C13 C9 N2 C6 179.1(4) . . . . ?
C8 C9 N2 B1 176.9(3) . . . . ?
C13 C9 N2 B1 -3.6(6) . . . . ?
C5 C6 N2 C9 178.1(3) . . . . ?
C7 C6 N2 C9 -0.1(4) . . . . ?
C5 C6 N2 B1 0.8(5) . . . . ?
C7 C6 N2 B1 -177.4(3) . . . . ?
N1 B1 N2 C9 179.2(3) . . . . ?
C14 B1 N2 C9 61.8(5) . . . . ?
C15 B1 N2 C9 -66.8(5) . . . . ?
N1 B1 N2 C6 -4.0(5) . . . . ?
C14 B1 N2 C6 -121.4(4) . . . . ?
C15 B1 N2 C6 110.0(4) . . . . ?
C4 C3 C2 C1 0.8(4) . . . . ?
C11 C3 C2 C1 -177.8(4) . . . . ?
N1 C1 C2 C3 -1.1(5) . . . . ?
C10 C1 C2 C3 176.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.679
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.099

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, diethyl ether'
_exptl_crystal_preparation       ', Luminescent'
