# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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#  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.
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#  fide research purposes only. It may contain copyright material
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data_20131118

#==============================================================================
# CHEMICAL DATA

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 B Br2 F2 N3'
_chemical_formula_sum            'C25 H20 B Br2 F2 N3'
_chemical_formula_weight         571.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
'-x, -y, z+1/2'

_cell_length_a                   20.7561(8)
_cell_length_b                   8.0356(3)
_cell_length_c                   26.8757(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4482.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16625
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      68.31

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             2272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    4.893
_shelx_estimated_absorpt_T_min   0.399
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.383
_exptl_absorpt_correction_T_max  0.863

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Varimax 40 kV 30 mA Rotating anode'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            48965
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.289
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_full        67.687
_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             8182
_reflns_number_gt                6839
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.999

_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       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1400P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8182
_refine_ls_number_parameters     656
_refine_ls_number_restraints     301
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2017
_refine_ls_wR_factor_gt          0.1918
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.025
_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
Br1 Br 1.22365(7) 0.99544(17) -0.02855(7) 0.0682(4) Uani 1 1 d . . . . .
Br2 Br 0.64471(6) 0.78577(15) 0.12096(5) 0.0532(4) Uani 1 1 d . . . . .
Br3 Br 0.50238(7) 1.48582(18) 0.09655(7) 0.0655(4) Uani 1 1 d . . . . .
Br4 Br 1.08078(6) 1.29261(15) -0.05301(5) 0.0525(3) Uani 1 1 d . . . . .
F1 F 1.0738(4) 0.5933(13) -0.1718(3) 0.084(3) Uani 1 1 d . . . . .
F2 F 1.0364(5) 0.8509(11) -0.1833(3) 0.078(2) Uani 1 1 d . . . . .
F3 F 0.6574(4) 1.0822(11) 0.2384(3) 0.072(2) Uani 1 1 d . . . . .
F4 F 0.6844(5) 1.3518(11) 0.2533(3) 0.080(2) Uani 1 1 d . . . . .
N1 N 1.0771(6) 0.7788(13) -0.1015(4) 0.058(3) Uani 1 1 d . . . . .
N2 N 0.9740(6) 0.6675(15) -0.1325(4) 0.064(3) Uani 1 1 d . . . . .
N3 N 0.9129(5) 0.5225(12) 0.1495(4) 0.051(2) Uani 1 1 d . . . . .
N4 N 0.6509(6) 1.2767(13) 0.1706(4) 0.059(3) Uani 1 1 d . . . . .
N5 N 0.7558(6) 1.1786(12) 0.2028(4) 0.056(3) Uani 1 1 d . . . . .
N6 N 0.8154(5) 1.0069(12) -0.0786(4) 0.048(2) Uani 1 1 d . . . . .
C1 C 1.1338(6) 0.8582(17) -0.0985(6) 0.059(3) Uani 1 1 d . . . . .
H1 H 1.1595 0.8899 -0.1262 0.071 Uiso 1 1 calc R U . . .
C2 C 1.1486(6) 0.8856(16) -0.0522(7) 0.061(3) Uani 1 1 d . . . . .
C3 C 1.1000(7) 0.8262(16) -0.0216(5) 0.056(3) Uani 1 1 d . . . . .
H3 H 1.0985 0.8309 0.0137 0.068 Uiso 1 1 calc R U . . .
C4 C 1.0528(6) 0.7573(14) -0.0536(5) 0.049(3) Uani 1 1 d . . . . .
C5 C 0.9938(6) 0.6850(14) -0.0434(5) 0.048(3) Uani 1 1 d . . . . .
C6 C 0.9538(7) 0.6392(15) -0.0843(4) 0.055(3) Uani 1 1 d . . . . .
C7 C 0.8918(6) 0.5597(17) -0.0859(5) 0.057(3) Uani 1 1 d . . . . .
H7 H 0.8666 0.5269 -0.0581 0.068 Uiso 1 1 calc R U . . .
C8 C 0.8762(9) 0.540(2) -0.1343(7) 0.077(5) Uani 1 1 d . . . . .
H8 H 0.8381 0.4895 -0.1468 0.092 Uiso 1 1 calc R U . . .
C9 C 0.9248(9) 0.606(2) -0.1622(6) 0.078(5) Uani 1 1 d . . . . .
H9 H 0.9249 0.6096 -0.1975 0.094 Uiso 1 1 calc R U . . .
C10 C 0.9401(6) 0.5560(15) 0.1044(4) 0.048(3) Uani 1 1 d . . . . .
C11 C 1.0014(6) 0.5211(14) 0.0883(5) 0.048(3) Uani 1 1 d . . . . .
H11 H 1.0317 0.4665 0.1092 0.058 Uiso 1 1 calc R U . . .
C12 C 1.0176(6) 0.5695(14) 0.0394(4) 0.046(2) Uani 1 1 d . . . . .
H12 H 1.0600 0.5478 0.0278 0.055 Uiso 1 1 calc R U . . .
C13 C 0.9736(6) 0.6489(13) 0.0068(4) 0.042(2) Uani 1 1 d . . . . .
C14 C 0.9112(6) 0.6822(14) 0.0252(4) 0.045(2) Uani 1 1 d . . . . .
H14 H 0.8807 0.7357 0.0043 0.054 Uiso 1 1 calc R U . . .
C15 C 0.8935(5) 0.6376(13) 0.0738(4) 0.044(2) Uani 1 1 d . . . . .
C16 C 0.8356(5) 0.6526(13) 0.1036(4) 0.042(2) Uani 1 1 d . . . . .
C17 C 0.7739(6) 0.7152(13) 0.0931(5) 0.047(3) Uani 1 1 d . . . . .
H17 H 0.7631 0.7607 0.0616 0.056 Uiso 1 1 calc R U . . .
C18 C 0.7306(6) 0.7064(13) 0.1314(4) 0.046(3) Uani 1 1 d . . . . .
C19 C 0.7447(6) 0.6396(15) 0.1780(5) 0.052(3) Uani 1 1 d . . . . .
H19 H 0.7125 0.6388 0.2031 0.062 Uiso 1 1 calc R U . . .
C20 C 0.8045(5) 0.5748(17) 0.1881(4) 0.050(3) Uani 1 1 d . . . . .
H20 H 0.8143 0.5288 0.2198 0.060 Uiso 1 1 calc R U . . .
C21 C 0.8506(6) 0.5792(15) 0.1498(4) 0.048(3) Uani 1 1 d . . . . .
C22 C 0.9452(7) 0.4425(18) 0.1916(5) 0.061(3) Uani 0.639(18) 1 d D U P A 1
H22A H 0.9591 0.3297 0.1814 0.074 Uiso 0.639(18) 1 calc R U P A 1
H22B H 0.9137 0.4295 0.2191 0.074 Uiso 0.639(18) 1 calc R U P A 1
C23 C 1.0033(9) 0.536(2) 0.2111(8) 0.058(3) Uani 0.639(18) 1 d D U P A 1
H23A H 1.0240 0.4730 0.2384 0.069 Uiso 0.639(18) 1 calc R U P A 1
H23B H 1.0353 0.5521 0.1842 0.069 Uiso 0.639(18) 1 calc R U P A 1
C24 C 0.9805(10) 0.704(2) 0.2301(8) 0.058(4) Uani 0.639(18) 1 d D U P A 1
H24A H 0.9465 0.6854 0.2553 0.069 Uiso 0.639(18) 1 calc R U P A 1
H24B H 0.9611 0.7662 0.2021 0.069 Uiso 0.639(18) 1 calc R U P A 1
C25 C 1.0345(10) 0.809(3) 0.2533(8) 0.048(4) Uani 0.639(18) 1 d D U P A 1
H25A H 1.0480 0.7592 0.2849 0.072 Uiso 0.639(18) 1 calc R U P A 1
H25B H 1.0186 0.9223 0.2594 0.072 Uiso 0.639(18) 1 calc R U P A 1
H25C H 1.0713 0.8136 0.2305 0.072 Uiso 0.639(18) 1 calc R U P A 1
C22A C 0.9452(7) 0.4425(18) 0.1916(5) 0.061(3) Uani 0.361(18) 1 d D U P A 2
H22C H 0.9830 0.3786 0.1798 0.074 Uiso 0.361(18) 1 calc R U P A 2
H22D H 0.9152 0.3643 0.2083 0.074 Uiso 0.361(18) 1 calc R U P A 2
C23A C 0.9674(17) 0.580(4) 0.2293(11) 0.058(4) Uani 0.361(18) 1 d D U P A 2
H23C H 0.9301 0.6535 0.2355 0.069 Uiso 0.361(18) 1 calc R U P A 2
H23D H 0.9774 0.5235 0.2612 0.069 Uiso 0.361(18) 1 calc R U P A 2
C24A C 1.0255(17) 0.692(4) 0.2162(12) 0.057(4) Uani 0.361(18) 1 d D U P A 2
H24C H 1.0109 0.7682 0.1895 0.068 Uiso 0.361(18) 1 calc R U P A 2
H24D H 1.0585 0.6186 0.2011 0.068 Uiso 0.361(18) 1 calc R U P A 2
C25A C 1.061(2) 0.801(6) 0.2553(16) 0.056(7) Uani 0.361(18) 1 d D U P A 2
H25D H 1.0426 0.9134 0.2551 0.084 Uiso 0.361(18) 1 calc R U P A 2
H25E H 1.1068 0.8067 0.2471 0.084 Uiso 0.361(18) 1 calc R U P A 2
H25F H 1.0555 0.7517 0.2884 0.084 Uiso 0.361(18) 1 calc R U P A 2
C26 C 0.5924(6) 1.3481(16) 0.1683(5) 0.056(3) Uani 1 1 d . . . . .
H26 H 0.5659 1.3741 0.1960 0.067 Uiso 1 1 calc R U . . .
C27 C 0.5767(5) 1.3784(15) 0.1180(5) 0.054(3) Uani 1 1 d . . . . .
C28 C 0.6283(6) 1.3216(15) 0.0887(5) 0.052(3) Uani 1 1 d . . . . .
H28 H 0.6320 1.3283 0.0535 0.062 Uiso 1 1 calc R U . . .
C29 C 0.6732(7) 1.2532(14) 0.1217(5) 0.056(3) Uani 1 1 d . . . . .
C30 C 0.7348(6) 1.1846(13) 0.1136(4) 0.045(3) Uani 1 1 d . . . . .
C31 C 0.7741(7) 1.1465(15) 0.1529(5) 0.056(3) Uani 1 1 d . . . . .
C32 C 0.8365(7) 1.0738(15) 0.1558(5) 0.060(3) Uani 1 1 d . . . . .
H32 H 0.8616 1.0345 0.1287 0.072 Uiso 1 1 calc R U . . .
C33 C 0.8536(7) 1.0712(18) 0.2055(5) 0.061(3) Uani 1 1 d . . . . .
H33 H 0.8932 1.0318 0.2188 0.073 Uiso 1 1 calc R U . . .
C34 C 0.8023(8) 1.137(2) 0.2329(6) 0.073(4) Uani 1 1 d . . . . .
H34 H 0.8014 1.1497 0.2681 0.087 Uiso 1 1 calc R U . . .
C35 C 0.7861(6) 1.0418(15) -0.0337(4) 0.048(3) Uani 1 1 d . . . . .
C36 C 0.7257(7) 1.0100(13) -0.0170(5) 0.052(3) Uani 1 1 d . . . . .
H36 H 0.6951 0.9540 -0.0373 0.062 Uiso 1 1 calc R U . . .
C37 C 0.7105(6) 1.0619(16) 0.0303(4) 0.051(3) Uani 1 1 d . . . . .
H37 H 0.6684 1.0405 0.0426 0.061 Uiso 1 1 calc R U . . .
C38 C 0.7544(6) 1.1450(16) 0.0614(4) 0.048(3) Uani 1 1 d . . . . .
C39 C 0.8162(6) 1.1793(14) 0.0440(4) 0.047(3) Uani 1 1 d . . . . .
H39 H 0.8464 1.2363 0.0644 0.056 Uiso 1 1 calc R U . . .
C40 C 0.8328(5) 1.1289(13) -0.0034(4) 0.042(2) Uani 1 1 d . . . . .
C41 C 0.8921(5) 1.1412(13) -0.0324(4) 0.044(2) Uani 1 1 d . . . . .
C42 C 0.9507(5) 1.2126(12) -0.0242(4) 0.040(2) Uani 1 1 d . . . . .
H42 H 0.9602 1.2661 0.0065 0.048 Uiso 1 1 calc R U . . .
C43 C 0.9960(5) 1.2046(14) -0.0621(5) 0.047(3) Uani 1 1 d . . . . .
C44 C 0.9837(6) 1.1315(15) -0.1084(4) 0.050(3) Uani 1 1 d . . . . .
H44 H 1.0160 1.1294 -0.1335 0.060 Uiso 1 1 calc R U . . .
C45 C 0.9235(5) 1.0621(14) -0.1171(4) 0.045(2) Uani 1 1 d . . . . .
H45 H 0.9137 1.0114 -0.1482 0.054 Uiso 1 1 calc R U . . .
C46 C 0.8785(5) 1.0686(15) -0.0796(4) 0.044(2) Uani 1 1 d . . . . .
C47 C 0.7815(6) 0.9209(16) -0.1204(5) 0.057(3) Uani 0.56(2) 1 d D U P B 3
H47A H 0.8139 0.8856 -0.1453 0.069 Uiso 0.56(2) 1 calc R U P B 3
H47B H 0.7605 0.8193 -0.1074 0.069 Uiso 0.56(2) 1 calc R U P B 3
C48 C 0.7327(12) 1.024(3) -0.1454(10) 0.058(5) Uani 0.56(2) 1 d D U P B 3
H48A H 0.6989 1.0561 -0.1213 0.070 Uiso 0.56(2) 1 calc R U P B 3
H48B H 0.7121 0.9590 -0.1725 0.070 Uiso 0.56(2) 1 calc R U P B 3
C49 C 0.7651(13) 1.181(3) -0.1671(11) 0.075(6) Uani 0.56(2) 1 d D U P B 3
H49A H 0.7920 1.1513 -0.1963 0.090 Uiso 0.56(2) 1 calc R U P B 3
H49B H 0.7931 1.2338 -0.1418 0.090 Uiso 0.56(2) 1 calc R U P B 3
C50 C 0.7106(19) 1.303(5) -0.183(2) 0.091(12) Uani 0.56(2) 1 d D U P B 3
H50A H 0.6833 1.2496 -0.2081 0.137 Uiso 0.56(2) 1 calc R U P B 3
H50B H 0.7297 1.4042 -0.1970 0.137 Uiso 0.56(2) 1 calc R U P B 3
H50C H 0.6845 1.3320 -0.1539 0.137 Uiso 0.56(2) 1 calc R U P B 3
C47A C 0.7815(6) 0.9209(16) -0.1204(5) 0.057(3) Uani 0.44(2) 1 d D U P B 4
H47C H 0.7426 0.8627 -0.1081 0.069 Uiso 0.44(2) 1 calc R U P B 4
H47D H 0.8103 0.8382 -0.1362 0.069 Uiso 0.44(2) 1 calc R U P B 4
C48A C 0.7622(16) 1.061(4) -0.1591(10) 0.059(6) Uani 0.44(2) 1 d D U P B 4
H48C H 0.7998 1.1343 -0.1647 0.070 Uiso 0.44(2) 1 calc R U P B 4
H48D H 0.7512 1.0078 -0.1912 0.070 Uiso 0.44(2) 1 calc R U P B 4
C49A C 0.7048(15) 1.168(4) -0.1419(10) 0.057(6) Uani 0.44(2) 1 d D U P B 4
H49C H 0.6684 1.0939 -0.1328 0.068 Uiso 0.44(2) 1 calc R U P B 4
H49D H 0.7173 1.2315 -0.1119 0.068 Uiso 0.44(2) 1 calc R U P B 4
C50A C 0.683(2) 1.288(6) -0.1825(18) 0.074(11) Uani 0.44(2) 1 d D U P B 4
H50D H 0.6974 1.4010 -0.1742 0.111 Uiso 0.44(2) 1 calc R U P B 4
H50E H 0.6358 1.2865 -0.1848 0.111 Uiso 0.44(2) 1 calc R U P B 4
H50F H 0.7015 1.2545 -0.2144 0.111 Uiso 0.44(2) 1 calc R U P B 4
B1 B 1.0393(10) 0.722(2) -0.1497(6) 0.065(5) Uani 1 1 d . . . . .
B2 B 0.6849(10) 1.219(2) 0.2186(6) 0.064(4) 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
Br1 C2 1.899(15) . ?
Br2 C18 1.914(13) . ?
Br3 C27 1.859(13) . ?
Br4 C43 1.912(12) . ?
F1 B1 1.394(16) . ?
F2 B1 1.372(18) . ?
F3 B2 1.347(19) . ?
F4 B2 1.420(18) . ?
N1 C1 1.341(18) . ?
N1 C4 1.394(17) . ?
N1 B1 1.58(2) . ?
N2 C6 1.382(17) . ?
N2 C9 1.387(19) . ?
N2 B1 1.50(2) . ?
N3 C10 1.364(16) . ?
N3 C21 1.372(16) . ?
N3 C22 1.464(16) . ?
N4 C26 1.344(18) . ?
N4 C29 1.407(17) . ?
N4 B2 1.54(2) . ?
N5 C34 1.303(19) . ?
N5 C31 1.417(17) . ?
N5 B2 1.57(2) . ?
N6 C35 1.380(15) . ?
N6 C46 1.401(15) . ?
N6 C47 1.494(15) . ?
C1 C2 1.30(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(17) . ?
C3 C4 1.42(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(18) . ?
C5 C6 1.425(17) . ?
C5 C13 1.442(17) . ?
C6 C7 1.438(18) . ?
C7 C8 1.35(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.36(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.374(18) . ?
C10 C15 1.428(16) . ?
C11 C12 1.410(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.417(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.411(16) . ?
C14 C15 1.404(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.449(16) . ?
C16 C17 1.403(16) . ?
C16 C21 1.409(16) . ?
C17 C18 1.369(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(17) . ?
C19 C20 1.372(17) . ?
C19 H19 0.9500 . ?
C20 C21 1.407(16) . ?
C20 H20 0.9500 . ?
C22 C23 1.52(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.51(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.54(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C23A C24A 1.55(3) . ?
C23A H23C 0.9900 . ?
C23A H23D 0.9900 . ?
C24A C25A 1.55(3) . ?
C24A H24C 0.9900 . ?
C24A H24D 0.9900 . ?
C25A H25D 0.9800 . ?
C25A H25E 0.9800 . ?
C25A H25F 0.9800 . ?
C26 C27 1.41(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.406(17) . ?
C28 C29 1.40(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.409(18) . ?
C30 C31 1.368(18) . ?
C30 C38 1.496(16) . ?
C31 C32 1.422(19) . ?
C32 C33 1.383(19) . ?
C32 H32 0.9500 . ?
C33 C34 1.40(2) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.354(19) . ?
C35 C40 1.448(16) . ?
C36 C37 1.377(18) . ?
C36 H36 0.9500 . ?
C37 C38 1.405(18) . ?
C37 H37 0.9500 . ?
C38 C39 1.392(16) . ?
C39 C40 1.381(16) . ?
C39 H39 0.9500 . ?
C40 C41 1.459(15) . ?
C41 C42 1.362(16) . ?
C41 C46 1.427(16) . ?
C42 C43 1.389(16) . ?
C42 H42 0.9500 . ?
C43 C44 1.401(17) . ?
C44 C45 1.388(17) . ?
C44 H44 0.9500 . ?
C45 C46 1.375(15) . ?
C45 H45 0.9500 . ?
C47 C48 1.47(2) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 C49 1.55(2) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C50 1.56(3) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C48A C49A 1.54(2) . ?
C48A H48C 0.9900 . ?
C48A H48D 0.9900 . ?
C49A C50A 1.53(3) . ?
C49A H49C 0.9900 . ?
C49A H49D 0.9900 . ?
C50A H50D 0.9800 . ?
C50A H50E 0.9800 . ?
C50A H50F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 108.6(12) . . ?
C1 N1 B1 128.5(12) . . ?
C4 N1 B1 122.8(13) . . ?
C6 N2 C9 104.9(14) . . ?
C6 N2 B1 127.7(12) . . ?
C9 N2 B1 126.5(13) . . ?
C10 N3 C21 109.2(10) . . ?
C10 N3 C22 125.9(11) . . ?
C21 N3 C22 125.0(10) . . ?
C26 N4 C29 108.1(12) . . ?
C26 N4 B2 125.5(12) . . ?
C29 N4 B2 126.2(12) . . ?
C34 N5 C31 110.1(12) . . ?
C34 N5 B2 125.4(12) . . ?
C31 N5 B2 123.1(12) . . ?
C35 N6 C46 110.9(9) . . ?
C35 N6 C47 123.0(10) . . ?
C46 N6 C47 126.1(10) . . ?
C2 C1 N1 110.3(12) . . ?
C2 C1 H1 124.9 . . ?
N1 C1 H1 124.9 . . ?
C1 C2 C3 109.6(14) . . ?
C1 C2 Br1 126.3(11) . . ?
C3 C2 Br1 124.0(13) . . ?
C2 C3 C4 106.2(13) . . ?
C2 C3 H3 126.9 . . ?
C4 C3 H3 126.9 . . ?
C5 C4 N1 123.8(13) . . ?
C5 C4 C3 131.0(13) . . ?
N1 C4 C3 105.3(12) . . ?
C4 C5 C6 118.1(12) . . ?
C4 C5 C13 121.9(11) . . ?
C6 C5 C13 120.0(11) . . ?
N2 C6 C5 120.3(13) . . ?
N2 C6 C7 108.4(11) . . ?
C5 C6 C7 131.2(12) . . ?
C8 C7 C6 107.2(15) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C7 C8 C9 107.9(16) . . ?
C7 C8 H8 126.1 . . ?
C9 C8 H8 126.1 . . ?
C8 C9 N2 111.6(14) . . ?
C8 C9 H9 124.2 . . ?
N2 C9 H9 124.2 . . ?
N3 C10 C11 128.5(11) . . ?
N3 C10 C15 108.8(11) . . ?
C11 C10 C15 122.7(11) . . ?
C10 C11 C12 117.3(11) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C11 C12 C13 123.1(11) . . ?
C11 C12 H12 118.4 . . ?
C13 C12 H12 118.4 . . ?
C14 C13 C12 117.3(11) . . ?
C14 C13 C5 123.8(10) . . ?
C12 C13 C5 118.8(11) . . ?
C15 C14 C13 121.3(10) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C10 118.3(11) . . ?
C14 C15 C16 135.3(10) . . ?
C10 C15 C16 106.4(10) . . ?
C17 C16 C21 121.9(11) . . ?
C17 C16 C15 132.5(10) . . ?
C21 C16 C15 105.6(10) . . ?
C18 C17 C16 115.5(11) . . ?
C18 C17 H17 122.3 . . ?
C16 C17 H17 122.3 . . ?
C17 C18 C19 123.9(12) . . ?
C17 C18 Br2 119.0(9) . . ?
C19 C18 Br2 117.1(9) . . ?
C20 C19 C18 121.0(12) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 117.4(11) . . ?
C19 C20 H20 121.3 . . ?
C21 C20 H20 121.3 . . ?
N3 C21 C20 129.6(11) . . ?
N3 C21 C16 110.1(10) . . ?
C20 C21 C16 120.3(11) . . ?
N3 C22 C23 114.3(13) . . ?
N3 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
N3 C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 108.0(16) . . ?
C24 C23 H23A 110.1 . . ?
C22 C23 H23A 110.1 . . ?
C24 C23 H23B 110.1 . . ?
C22 C23 H23B 110.1 . . ?
H23A C23 H23B 108.4 . . ?
C23 C24 C25 113.5(18) . . ?
C23 C24 H24A 108.9 . . ?
C25 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
C25 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24A C23A H23C 107.4 . . ?
C24A C23A H23D 107.4 . . ?
H23C C23A H23D 107.0 . . ?
C23A C24A C25A 123(3) . . ?
C23A C24A H24C 106.6 . . ?
C25A C24A H24C 106.6 . . ?
C23A C24A H24D 106.6 . . ?
C25A C24A H24D 106.6 . . ?
H24C C24A H24D 106.6 . . ?
C24A C25A H25D 109.5 . . ?
C24A C25A H25E 109.5 . . ?
H25D C25A H25E 109.5 . . ?
C24A C25A H25F 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?
N4 C26 C27 109.1(11) . . ?
N4 C26 H26 125.4 . . ?
C27 C26 H26 125.4 . . ?
C28 C27 C26 107.7(12) . . ?
C28 C27 Br3 127.5(11) . . ?
C26 C27 Br3 124.7(9) . . ?
C29 C28 C27 106.3(12) . . ?
C29 C28 H28 126.9 . . ?
C27 C28 H28 126.9 . . ?
C28 C29 N4 108.7(12) . . ?
C28 C29 C30 131.4(13) . . ?
N4 C29 C30 119.6(13) . . ?
C31 C30 C29 120.7(11) . . ?
C31 C30 C38 120.9(11) . . ?
C29 C30 C38 118.3(11) . . ?
C30 C31 N5 122.0(12) . . ?
C30 C31 C32 132.6(12) . . ?
N5 C31 C32 105.4(11) . . ?
C33 C32 C31 107.1(12) . . ?
C33 C32 H32 126.4 . . ?
C31 C32 H32 126.4 . . ?
C32 C33 C34 107.8(13) . . ?
C32 C33 H33 126.1 . . ?
C34 C33 H33 126.1 . . ?
N5 C34 C33 109.4(14) . . ?
N5 C34 H34 125.3 . . ?
C33 C34 H34 125.3 . . ?
C36 C35 N6 131.2(11) . . ?
C36 C35 C40 121.6(11) . . ?
N6 C35 C40 107.2(10) . . ?
C35 C36 C37 117.5(12) . . ?
C35 C36 H36 121.3 . . ?
C37 C36 H36 121.3 . . ?
C36 C37 C38 123.0(12) . . ?
C36 C37 H37 118.5 . . ?
C38 C37 H37 118.5 . . ?
C39 C38 C37 119.5(11) . . ?
C39 C38 C30 121.6(11) . . ?
C37 C38 C30 118.8(10) . . ?
C40 C39 C38 118.8(11) . . ?
C40 C39 H39 120.6 . . ?
C38 C39 H39 120.6 . . ?
C39 C40 C35 119.6(10) . . ?
C39 C40 C41 133.1(11) . . ?
C35 C40 C41 107.3(10) . . ?
C42 C41 C46 119.5(10) . . ?
C42 C41 C40 134.0(10) . . ?
C46 C41 C40 106.3(10) . . ?
C41 C42 C43 117.8(10) . . ?
C41 C42 H42 121.1 . . ?
C43 C42 H42 121.1 . . ?
C42 C43 C44 123.2(11) . . ?
C42 C43 Br4 120.9(9) . . ?
C44 C43 Br4 115.9(9) . . ?
C45 C44 C43 118.8(11) . . ?
C45 C44 H44 120.6 . . ?
C43 C44 H44 120.6 . . ?
C46 C45 C44 118.2(11) . . ?
C46 C45 H45 120.9 . . ?
C44 C45 H45 120.9 . . ?
C45 C46 N6 129.5(10) . . ?
C45 C46 C41 122.3(10) . . ?
N6 C46 C41 108.2(10) . . ?
C48 C47 N6 114.1(13) . . ?
C48 C47 H47A 108.7 . . ?
N6 C47 H47A 108.7 . . ?
C48 C47 H47B 108.7 . . ?
N6 C47 H47B 108.7 . . ?
H47A C47 H47B 107.6 . . ?
C47 C48 C49 109.3(19) . . ?
C47 C48 H48A 109.8 . . ?
C49 C48 H48A 109.8 . . ?
C47 C48 H48B 109.8 . . ?
C49 C48 H48B 109.8 . . ?
H48A C48 H48B 108.3 . . ?
C48 C49 C50 108(2) . . ?
C48 C49 H49A 110.2 . . ?
C50 C49 H49A 110.2 . . ?
C48 C49 H49B 110.2 . . ?
C50 C49 H49B 110.2 . . ?
H49A C49 H49B 108.5 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C49A C48A H48C 108.9 . . ?
C49A C48A H48D 108.9 . . ?
H48C C48A H48D 107.7 . . ?
C50A C49A C48A 112(3) . . ?
C50A C49A H49C 109.3 . . ?
C48A C49A H49C 109.3 . . ?
C50A C49A H49D 109.3 . . ?
C48A C49A H49D 109.3 . . ?
H49C C49A H49D 107.9 . . ?
C49A C50A H50D 109.5 . . ?
C49A C50A H50E 109.5 . . ?
H50D C50A H50E 109.5 . . ?
C49A C50A H50F 109.5 . . ?
H50D C50A H50F 109.5 . . ?
H50E C50A H50F 109.5 . . ?
F2 B1 F1 107.6(12) . . ?
F2 B1 N2 112.7(13) . . ?
F1 B1 N2 112.1(14) . . ?
F2 B1 N1 110.1(14) . . ?
F1 B1 N1 107.9(12) . . ?
N2 B1 N1 106.4(11) . . ?
F3 B2 F4 110.5(12) . . ?
F3 B2 N4 112.6(14) . . ?
F4 B2 N4 108.6(13) . . ?
F3 B2 N5 109.8(13) . . ?
F4 B2 N5 109.9(13) . . ?
N4 B2 N5 105.4(11) . . ?

_refine_diff_density_max         2.294
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.155

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 979461'
#######################################################################
#
#                 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_20131101

#==============================================================================
# CHEMICAL DATA

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 B F2 N3'
_chemical_formula_sum            'C25 H22 B F2 N3'
_chemical_formula_weight         413.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.6130(4)
_cell_length_b                   18.4723(5)
_cell_length_c                   7.8475(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.506(7)
_cell_angle_gamma                90
_cell_volume                     2050.80(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14994
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      68.17

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.745
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_T_max  0.928

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Varimax 40 kV 30 mA Rotating anode'
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            24071
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.124
_diffrn_reflns_theta_max         68.231
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3753
_reflns_number_gt                3503
_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       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

_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)+(0.0500P)²+0.7760P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3753
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
F1 F 0.31057(5) 0.08110(4) 0.14734(10) 0.02901(19) Uani 1 1 d . . . . .
F2 F 0.38198(5) 0.07297(4) -0.07678(10) 0.02904(19) Uani 1 1 d . . . . .
N1 N 0.37356(7) 0.19085(6) 0.05162(14) 0.0229(2) Uani 1 1 d . . . . .
N2 N 0.47967(7) 0.09647(5) 0.21565(14) 0.0226(2) Uani 1 1 d . . . . .
N3 N 0.82978(7) 0.41140(5) 0.51483(14) 0.0221(2) Uani 1 1 d . . . . .
C1 C 0.30017(9) 0.22462(7) -0.05694(17) 0.0267(3) Uani 1 1 d . . . . .
H1 H 0.2449 0.2012 -0.1238 0.032 Uiso 1 1 calc R U . . .
C2 C 0.31662(9) 0.29895(7) -0.05742(18) 0.0277(3) Uani 1 1 d . . . . .
H2 H 0.2749 0.3346 -0.1210 0.033 Uiso 1 1 calc R U . . .
C3 C 0.40546(9) 0.31078(7) 0.05247(17) 0.0243(3) Uani 1 1 d . . . . .
H3 H 0.4366 0.3562 0.0765 0.029 Uiso 1 1 calc R U . . .
C4 C 0.44126(8) 0.24325(7) 0.12213(16) 0.0217(3) Uani 1 1 d . . . . .
C5 C 0.52806(8) 0.22324(6) 0.23609(16) 0.0204(3) Uani 1 1 d . . . . .
C6 C 0.54463(8) 0.15046(7) 0.28695(16) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.61857(9) 0.11783(7) 0.41491(17) 0.0233(3) Uani 1 1 d . . . . .
H7 H 0.6724 0.1416 0.4859 0.028 Uiso 1 1 calc R U . . .
C8 C 0.59816(9) 0.04484(7) 0.41762(18) 0.0279(3) Uani 1 1 d . . . . .
H8 H 0.6353 0.0090 0.4903 0.033 Uiso 1 1 calc R U . . .
C9 C 0.51260(9) 0.03381(7) 0.29340(18) 0.0274(3) Uani 1 1 d . . . . .
H9 H 0.4820 -0.0117 0.2675 0.033 Uiso 1 1 calc R U . . .
C10 C 0.74726(9) 0.37375(6) 0.44684(16) 0.0208(3) Uani 1 1 d . . . . .
C11 C 0.65496(9) 0.39120(6) 0.45096(16) 0.0215(3) Uani 1 1 d . . . . .
H11 H 0.6412 0.4349 0.5034 0.026 Uiso 1 1 calc R U . . .
C12 C 0.58409(9) 0.34278(6) 0.37615(16) 0.0210(3) Uani 1 1 d . . . . .
H12 H 0.5205 0.3544 0.3743 0.025 Uiso 1 1 calc R U . . .
C13 C 0.60368(8) 0.27654(6) 0.30244(16) 0.0205(3) Uani 1 1 d . . . . .
C14 C 0.69624(8) 0.26030(6) 0.29683(16) 0.0210(3) Uani 1 1 d . . . . .
H14 H 0.7098 0.2164 0.2452 0.025 Uiso 1 1 calc R U . . .
C15 C 0.76838(8) 0.30899(6) 0.36739(16) 0.0207(3) Uani 1 1 d . . . . .
C16 C 0.86994(9) 0.30824(7) 0.38989(16) 0.0225(3) Uani 1 1 d . . . . .
C17 C 0.93310(9) 0.25987(7) 0.34402(18) 0.0277(3) Uani 1 1 d . . . . .
H17 H 0.9108 0.2173 0.2790 0.033 Uiso 1 1 calc R U . . .
C18 C 1.02893(10) 0.27498(8) 0.3948(2) 0.0335(3) Uani 1 1 d . . . . .
H18 H 1.0726 0.2424 0.3645 0.040 Uiso 1 1 calc R U . . .
C19 C 1.06215(9) 0.33777(8) 0.4903(2) 0.0330(3) Uani 1 1 d . . . . .
H19 H 1.1282 0.3469 0.5244 0.040 Uiso 1 1 calc R U . . .
C20 C 1.00101(9) 0.38682(7) 0.53615(18) 0.0277(3) Uani 1 1 d . . . . .
H20 H 1.0239 0.4294 0.6008 0.033 Uiso 1 1 calc R U . . .
C21 C 0.90470(9) 0.37158(7) 0.48411(16) 0.0225(3) Uani 1 1 d . . . . .
C22 C 0.83810(9) 0.47454(6) 0.62914(17) 0.0242(3) Uani 1 1 d . . . . .
H22A H 0.7809 0.5050 0.5898 0.029 Uiso 1 1 calc R U . . .
H22B H 0.8933 0.5037 0.6187 0.029 Uiso 1 1 calc R U . . .
C23 C 0.84970(9) 0.45362(7) 0.82081(17) 0.0271(3) Uani 1 1 d . . . . .
H23A H 0.8003 0.4179 0.8283 0.032 Uiso 1 1 calc R U . . .
H23B H 0.9120 0.4301 0.8653 0.032 Uiso 1 1 calc R U . . .
C24 C 0.84272(10) 0.51794(8) 0.93755(19) 0.0333(3) Uani 1 1 d . . . . .
H24A H 0.7818 0.5431 0.8902 0.040 Uiso 1 1 calc R U . . .
H24B H 0.8943 0.5525 0.9360 0.040 Uiso 1 1 calc R U . . .
C25 C 0.84945(11) 0.49452(10) 1.1265(2) 0.0419(4) Uani 1 1 d . . . . .
H25A H 0.9126 0.4749 1.1784 0.050 Uiso 1 1 calc R U . . .
H25B H 0.8018 0.4573 1.1274 0.050 Uiso 1 1 calc R U . . .
H25C H 0.8382 0.5364 1.1954 0.050 Uiso 1 1 calc R U . . .
B1 B 0.38362(10) 0.10816(8) 0.0811(2) 0.0240(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
F1 B1 1.3920(16) . ?
F2 B1 1.3939(17) . ?
N1 C1 1.3444(17) . ?
N1 C4 1.3955(16) . ?
N1 B1 1.5463(17) . ?
N2 C9 1.3403(17) . ?
N2 C6 1.3938(15) . ?
N2 B1 1.5458(18) . ?
N3 C10 1.3785(16) . ?
N3 C21 1.3891(16) . ?
N3 C22 1.4579(15) . ?
C1 C2 1.3941(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.3842(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.4090(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.4060(17) . ?
C5 C6 1.4061(17) . ?
C5 C13 1.4742(16) . ?
C6 C7 1.4126(18) . ?
C7 C8 1.3823(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3945(19) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.3949(17) . ?
C10 C15 1.4183(17) . ?
C11 C12 1.3831(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.4130(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3968(17) . ?
C14 C15 1.3910(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.4500(17) . ?
C16 C17 1.3952(18) . ?
C16 C21 1.4091(17) . ?
C17 C18 1.3849(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.400(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.3925(18) . ?
C20 H20 0.9500 . ?
C22 C23 1.5208(18) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5192(18) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.524(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 107.65(10) . . ?
C1 N1 B1 125.73(11) . . ?
C4 N1 B1 126.47(10) . . ?
C9 N2 C6 107.73(10) . . ?
C9 N2 B1 126.35(10) . . ?
C6 N2 B1 125.79(10) . . ?
C10 N3 C21 108.47(10) . . ?
C10 N3 C22 124.87(10) . . ?
C21 N3 C22 125.63(10) . . ?
N1 C1 C2 110.37(11) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C3 C2 C1 106.81(12) . . ?
C3 C2 H2 126.6 . . ?
C1 C2 H2 126.6 . . ?
C2 C3 C4 107.52(11) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
N1 C4 C5 120.45(11) . . ?
N1 C4 C3 107.63(11) . . ?
C5 C4 C3 131.88(11) . . ?
C6 C5 C4 119.71(11) . . ?
C6 C5 C13 118.54(11) . . ?
C4 C5 C13 121.74(11) . . ?
N2 C6 C5 121.25(11) . . ?
N2 C6 C7 107.62(11) . . ?
C5 C6 C7 131.02(11) . . ?
C8 C7 C6 107.31(11) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 106.91(12) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 110.42(11) . . ?
N2 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
N3 C10 C11 129.17(11) . . ?
N3 C10 C15 109.27(11) . . ?
C11 C10 C15 121.55(11) . . ?
C12 C11 C10 117.79(11) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C11 C12 C13 121.79(11) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 119.73(11) . . ?
C14 C13 C5 119.44(11) . . ?
C12 C13 C5 120.80(11) . . ?
C15 C14 C13 119.47(11) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 119.59(11) . . ?
C14 C15 C16 133.86(11) . . ?
C10 C15 C16 106.46(10) . . ?
C17 C16 C21 119.50(12) . . ?
C17 C16 C15 134.25(12) . . ?
C21 C16 C15 106.22(11) . . ?
C18 C17 C16 118.90(12) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 120.72(13) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 121.50(12) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 117.58(12) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 H20 121.2 . . ?
N3 C21 C20 128.66(12) . . ?
N3 C21 C16 109.55(11) . . ?
C20 C21 C16 121.78(12) . . ?
N3 C22 C23 112.13(10) . . ?
N3 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
N3 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C22 112.95(11) . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C25 111.53(12) . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F1 B1 F2 108.69(10) . . ?
F1 B1 N2 110.16(11) . . ?
F2 B1 N2 110.64(11) . . ?
F1 B1 N1 110.95(11) . . ?
F2 B1 N1 110.36(11) . . ?
N2 B1 N1 106.03(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -1.31(14) . . . . ?
B1 N1 C1 C2 -177.10(12) . . . . ?
N1 C1 C2 C3 1.69(15) . . . . ?
C1 C2 C3 C4 -1.37(15) . . . . ?
C1 N1 C4 C5 -177.55(11) . . . . ?
B1 N1 C4 C5 -1.80(18) . . . . ?
C1 N1 C4 C3 0.42(14) . . . . ?
B1 N1 C4 C3 176.17(11) . . . . ?
C2 C3 C4 N1 0.61(14) . . . . ?
C2 C3 C4 C5 178.26(13) . . . . ?
N1 C4 C5 C6 -3.52(18) . . . . ?
C3 C4 C5 C6 179.08(13) . . . . ?
N1 C4 C5 C13 175.47(11) . . . . ?
C3 C4 C5 C13 -1.9(2) . . . . ?
C9 N2 C6 C5 -177.65(11) . . . . ?
B1 N2 C6 C5 -1.70(18) . . . . ?
C9 N2 C6 C7 -0.96(13) . . . . ?
B1 N2 C6 C7 174.99(11) . . . . ?
C4 C5 C6 N2 5.20(18) . . . . ?
C13 C5 C6 N2 -173.82(11) . . . . ?
C4 C5 C6 C7 -170.61(12) . . . . ?
C13 C5 C6 C7 10.4(2) . . . . ?
N2 C6 C7 C8 0.80(14) . . . . ?
C5 C6 C7 C8 177.05(13) . . . . ?
C6 C7 C8 C9 -0.35(15) . . . . ?
C6 N2 C9 C8 0.75(15) . . . . ?
B1 N2 C9 C8 -175.16(12) . . . . ?
C7 C8 C9 N2 -0.25(16) . . . . ?
C21 N3 C10 C11 177.90(12) . . . . ?
C22 N3 C10 C11 9.0(2) . . . . ?
C21 N3 C10 C15 -1.15(14) . . . . ?
C22 N3 C10 C15 -170.09(11) . . . . ?
N3 C10 C11 C12 -178.33(12) . . . . ?
C15 C10 C11 C12 0.61(18) . . . . ?
C10 C11 C12 C13 1.97(18) . . . . ?
C11 C12 C13 C14 -2.99(18) . . . . ?
C11 C12 C13 C5 175.14(11) . . . . ?
C6 C5 C13 C14 46.10(16) . . . . ?
C4 C5 C13 C14 -132.90(13) . . . . ?
C6 C5 C13 C12 -132.04(12) . . . . ?
C4 C5 C13 C12 48.96(17) . . . . ?
C12 C13 C14 C15 1.34(18) . . . . ?
C5 C13 C14 C15 -176.81(11) . . . . ?
C13 C14 C15 C10 1.15(18) . . . . ?
C13 C14 C15 C16 177.05(13) . . . . ?
N3 C10 C15 C14 176.95(11) . . . . ?
C11 C10 C15 C14 -2.18(18) . . . . ?
N3 C10 C15 C16 0.03(13) . . . . ?
C11 C10 C15 C16 -179.10(11) . . . . ?
C14 C15 C16 C17 2.7(3) . . . . ?
C10 C15 C16 C17 179.01(14) . . . . ?
C14 C15 C16 C21 -175.22(13) . . . . ?
C10 C15 C16 C21 1.07(13) . . . . ?
C21 C16 C17 C18 0.9(2) . . . . ?
C15 C16 C17 C18 -176.82(14) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C10 N3 C21 C20 -176.90(13) . . . . ?
C22 N3 C21 C20 -8.1(2) . . . . ?
C10 N3 C21 C16 1.86(14) . . . . ?
C22 N3 C21 C16 170.69(11) . . . . ?
C19 C20 C21 N3 179.35(13) . . . . ?
C19 C20 C21 C16 0.7(2) . . . . ?
C17 C16 C21 N3 179.89(11) . . . . ?
C15 C16 C21 N3 -1.80(14) . . . . ?
C17 C16 C21 C20 -1.25(19) . . . . ?
C15 C16 C21 C20 177.06(12) . . . . ?
C10 N3 C22 C23 83.14(15) . . . . ?
C21 N3 C22 C23 -83.92(14) . . . . ?
N3 C22 C23 C24 -170.79(11) . . . . ?
C22 C23 C24 C25 176.99(11) . . . . ?
C9 N2 B1 F1 52.24(17) . . . . ?
C6 N2 B1 F1 -122.96(12) . . . . ?
C9 N2 B1 F2 -67.96(16) . . . . ?
C6 N2 B1 F2 116.84(13) . . . . ?
C9 N2 B1 N1 172.36(11) . . . . ?
C6 N2 B1 N1 -2.84(16) . . . . ?
C1 N1 B1 F1 -60.78(16) . . . . ?
C4 N1 B1 F1 124.21(12) . . . . ?
C1 N1 B1 F2 59.75(16) . . . . ?
C4 N1 B1 F2 -115.26(13) . . . . ?
C1 N1 B1 N2 179.61(11) . . . . ?
C4 N1 B1 N2 4.60(16) . . . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 982777'
