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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_rm124

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H34 B F2 N3'
_chemical_formula_weight         521.44

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'

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

_cell_length_a                   17.3150(5)
_cell_length_b                   16.0128(6)
_cell_length_c                   10.1781(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2822.00(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6064
_cell_measurement_theta_min      3.4610
_cell_measurement_theta_max      27.2710

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20965
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4886
_reflns_number_gt                4017
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0593P)²+0.3475P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.5(10)
_refine_ls_number_reflns         4886
_refine_ls_number_parameters     359
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1203
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.54208(17) 0.1315(2) 0.8886(3) 0.0441(7) Uani 1 1 d . . .
F1 F 0.56299(10) 0.21134(12) 0.85078(19) 0.0718(5) Uani 1 1 d . . .
F2 F 0.60475(9) 0.07857(12) 0.87751(17) 0.0658(5) Uani 1 1 d . . .
N1 N 0.51122(12) 0.13270(14) 1.0312(2) 0.0429(5) Uani 1 1 d . . .
N2 N 0.47527(12) 0.09935(14) 0.8029(2) 0.0433(5) Uani 1 1 d . . .
N3 N 0.10500(12) -0.05243(14) 0.9468(2) 0.0435(5) Uani 1 1 d . . .
C1 C 0.54460(17) 0.1672(2) 1.1362(3) 0.0617(8) Uani 1 1 d . . .
H1 H 0.5916 0.1978 1.1347 0.074 Uiso 1 1 calc R . .
C2 C 0.50058(19) 0.1519(3) 1.2488(3) 0.0709(10) Uani 1 1 d . . .
H2 H 0.5116 0.1708 1.3353 0.085 Uiso 1 1 calc R . .
C3 C 0.43851(17) 0.1047(2) 1.2107(3) 0.0567(8) Uani 1 1 d . . .
H3 H 0.3990 0.0837 1.2664 0.068 Uiso 1 1 calc R . .
C4 C 0.44414(14) 0.09306(17) 1.0742(3) 0.0420(6) Uani 1 1 d . . .
C5 C 0.39299(14) 0.05719(16) 0.9837(3) 0.0392(6) Uani 1 1 d . . .
C6 C 0.40853(14) 0.05998(16) 0.8493(3) 0.0408(6) Uani 1 1 d . . .
C7 C 0.36684(16) 0.0310(2) 0.7398(3) 0.0559(8) Uani 1 1 d . . .
H7 H 0.3193 0.0015 0.7419 0.067 Uiso 1 1 calc R . .
C8 C 0.40746(19) 0.0533(2) 0.6288(3) 0.0652(9) Uani 1 1 d . . .
H8 H 0.3931 0.0426 0.5403 0.078 Uiso 1 1 calc R . .
C9 C 0.47351(18) 0.0943(2) 0.6714(3) 0.0587(8) Uani 1 1 d . . .
H9 H 0.5123 0.1160 0.6149 0.070 Uiso 1 1 calc R . .
C10 C 0.32453(15) 0.01874(17) 1.0320(3) 0.0454(7) Uani 1 1 d . . .
C11 C 0.26636(14) -0.01299(16) 1.0737(3) 0.0426(6) Uani 1 1 d . . .
C12 C 0.20220(14) -0.05429(16) 1.1336(3) 0.0397(6) Uani 1 1 d . . .
C13 C 0.21179(14) -0.08200(16) 1.2632(3) 0.0412(6) Uani 1 1 d . . .
H13 H 0.2586 -0.0684 1.3070 0.049 Uiso 1 1 calc R . .
C14 C 0.15626(13) -0.12885(16) 1.3323(3) 0.0389(6) Uani 1 1 d . . .
C15 C 0.08846(14) -0.14978(16) 1.2648(3) 0.0406(6) Uani 1 1 d . . .
H15 H 0.0504 -0.1832 1.3068 0.049 Uiso 1 1 calc R . .
C16 C 0.07626(13) -0.12211(16) 1.1369(3) 0.0377(6) Uani 1 1 d . . .
C17 C 0.13213(13) -0.07388(15) 1.0706(3) 0.0378(6) Uani 1 1 d . . .
C18 C 0.03001(14) -0.08461(17) 0.9342(3) 0.0418(6) Uani 1 1 d . . .
C19 C -0.02246(16) -0.0768(2) 0.8322(3) 0.0520(7) Uani 1 1 d . . .
H19 H -0.0100 -0.0460 0.7553 0.062 Uiso 1 1 calc R . .
C20 C -0.09402(16) -0.11542(19) 0.8459(3) 0.0521(7) Uani 1 1 d . . .
H20 H -0.1304 -0.1101 0.7765 0.062 Uiso 1 1 calc R . .
C21 C -0.11516(15) -0.16191(17) 0.9573(3) 0.0441(6) Uani 1 1 d . . .
C22 C -0.06156(14) -0.16860(16) 1.0583(3) 0.0411(6) Uani 1 1 d . . .
H22 H -0.0741 -0.1997 1.1349 0.049 Uiso 1 1 calc R . .
C23 C 0.01060(13) -0.13007(17) 1.0483(3) 0.0381(6) Uani 1 1 d . . .
C24 C 0.17142(15) -0.15695(18) 1.4731(3) 0.0463(7) Uani 1 1 d . . .
C25 C 0.2180(2) -0.0934(3) 1.5504(3) 0.0782(11) Uani 1 1 d . . .
H25A H 0.2694 -0.0878 1.5113 0.117 Uiso 1 1 calc R . .
H25B H 0.2229 -0.1121 1.6417 0.117 Uiso 1 1 calc R . .
H25C H 0.1916 -0.0393 1.5481 0.117 Uiso 1 1 calc R . .
C26 C 0.2184(3) -0.2383(3) 1.4684(4) 0.0983(14) Uani 1 1 d . . .
H26A H 0.1897 -0.2807 1.4190 0.147 Uiso 1 1 calc R . .
H26B H 0.2276 -0.2583 1.5581 0.147 Uiso 1 1 calc R . .
H26C H 0.2681 -0.2278 1.4251 0.147 Uiso 1 1 calc R . .
C27 C 0.0968(2) -0.1713(3) 1.5483(4) 0.0981(16) Uani 1 1 d . . .
H27A H 0.0663 -0.1198 1.5485 0.147 Uiso 1 1 calc R . .
H27B H 0.1089 -0.1874 1.6389 0.147 Uiso 1 1 calc R . .
H27C H 0.0673 -0.2160 1.5059 0.147 Uiso 1 1 calc R . .
C28 C 0.13530(16) 0.01410(19) 0.8647(3) 0.0531(7) Uani 1 1 d . . .
H28A H 0.1117 0.0100 0.7763 0.064 Uiso 1 1 calc R . .
H28B H 0.1917 0.0064 0.8547 0.064 Uiso 1 1 calc R . .
C29 C 0.1201(2) 0.0994(2) 0.9194(4) 0.0803(11) Uani 1 1 d . . .
H29A H 0.0642 0.1083 0.9266 0.120 Uiso 1 1 calc R . .
H29B H 0.1423 0.1416 0.8609 0.120 Uiso 1 1 calc R . .
H29C H 0.1437 0.1041 1.0066 0.120 Uiso 1 1 calc R . .
C30 C -0.19519(15) -0.20409(18) 0.9657(3) 0.0460(6) Uani 1 1 d . . .
C31 C -0.2226(2) -0.2128(4) 1.1053(4) 0.1091(17) Uani 1 1 d . . .
H31A H -0.2742 -0.2379 1.1061 0.164 Uiso 1 1 calc R . .
H31B H -0.2247 -0.1576 1.1466 0.164 Uiso 1 1 calc R . .
H31C H -0.1868 -0.2486 1.1542 0.164 Uiso 1 1 calc R . .
C32 C -0.1906(2) -0.2905(2) 0.9063(5) 0.1068(17) Uani 1 1 d . . .
H32A H -0.2413 -0.3173 0.9111 0.160 Uiso 1 1 calc R . .
H32B H -0.1528 -0.3239 0.9550 0.160 Uiso 1 1 calc R . .
H32C H -0.1745 -0.2862 0.8142 0.160 Uiso 1 1 calc R . .
C33 C -0.2562(2) -0.1550(3) 0.8924(5) 0.1147(19) Uani 1 1 d . . .
H33A H -0.2429 -0.1528 0.7989 0.172 Uiso 1 1 calc R . .
H33B H -0.2587 -0.0981 0.9277 0.172 Uiso 1 1 calc R . .
H33C H -0.3065 -0.1822 0.9033 0.172 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
B1 F2 1.381(4) . ?
B1 F1 1.384(4) . ?
B1 N2 1.538(4) . ?
B1 N1 1.547(4) . ?
N1 C1 1.334(4) . ?
N1 C4 1.394(3) . ?
N2 C9 1.341(4) . ?
N2 C6 1.399(3) . ?
N3 C17 1.388(3) . ?
N3 C18 1.403(3) . ?
N3 C28 1.452(3) . ?
C1 C2 1.398(5) . ?
C2 C3 1.370(4) . ?
C3 C4 1.405(4) . ?
C4 C5 1.401(4) . ?
C5 C6 1.395(4) . ?
C5 C10 1.423(4) . ?
C6 C7 1.407(4) . ?
C7 C8 1.378(5) . ?
C8 C9 1.389(5) . ?
C10 C11 1.205(3) . ?
C11 C12 1.429(3) . ?
C12 C13 1.401(4) . ?
C12 C17 1.408(3) . ?
C13 C14 1.408(3) . ?
C14 C15 1.401(3) . ?
C14 C24 1.524(4) . ?
C15 C16 1.391(4) . ?
C16 C17 1.410(3) . ?
C16 C23 1.457(3) . ?
C18 C19 1.385(4) . ?
C18 C23 1.411(4) . ?
C19 C20 1.392(4) . ?
C20 C21 1.405(4) . ?
C21 C22 1.389(4) . ?
C21 C30 1.544(4) . ?
C22 C23 1.397(3) . ?
C24 C25 1.518(4) . ?
C24 C27 1.518(4) . ?
C24 C26 1.537(5) . ?
C28 C29 1.499(5) . ?
C30 C31 1.505(5) . ?
C30 C33 1.513(5) . ?
C30 C32 1.512(5) . ?

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
F2 B1 F1 109.8(2) . . ?
F2 B1 N2 109.9(2) . . ?
F1 B1 N2 110.4(2) . . ?
F2 B1 N1 110.9(2) . . ?
F1 B1 N1 109.8(2) . . ?
N2 B1 N1 106.1(2) . . ?
C1 N1 C4 107.3(2) . . ?
C1 N1 B1 127.4(2) . . ?
C4 N1 B1 125.2(2) . . ?
C9 N2 C6 106.9(2) . . ?
C9 N2 B1 127.1(2) . . ?
C6 N2 B1 125.5(2) . . ?
C17 N3 C18 107.8(2) . . ?
C17 N3 C28 125.6(2) . . ?
C18 N3 C28 123.5(2) . . ?
N1 C1 C2 110.3(3) . . ?
C3 C2 C1 107.0(3) . . ?
C2 C3 C4 107.3(3) . . ?
N1 C4 C3 107.9(2) . . ?
N1 C4 C5 120.5(2) . . ?
C3 C4 C5 131.3(2) . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 C10 120.9(2) . . ?
C4 C5 C10 118.5(2) . . ?
C5 C6 N2 120.4(2) . . ?
C5 C6 C7 131.9(2) . . ?
N2 C6 C7 107.7(2) . . ?
C8 C7 C6 107.6(3) . . ?
C7 C8 C9 106.7(3) . . ?
N2 C9 C8 111.0(3) . . ?
C11 C10 C5 179.2(3) . . ?
C10 C11 C12 174.1(3) . . ?
C13 C12 C17 117.4(2) . . ?
C13 C12 C11 117.1(2) . . ?
C17 C12 C11 125.3(2) . . ?
C12 C13 C14 123.9(2) . . ?
C15 C14 C13 117.0(2) . . ?
C15 C14 C24 122.3(2) . . ?
C13 C14 C24 120.6(2) . . ?
C16 C15 C14 120.7(2) . . ?
C15 C16 C17 121.2(2) . . ?
C15 C16 C23 132.1(2) . . ?
C17 C16 C23 106.7(2) . . ?
N3 C17 C12 130.6(2) . . ?
N3 C17 C16 109.8(2) . . ?
C12 C17 C16 119.7(2) . . ?
C19 C18 N3 130.0(2) . . ?
C19 C18 C23 120.5(2) . . ?
N3 C18 C23 109.6(2) . . ?
C18 C19 C20 117.9(3) . . ?
C19 C20 C21 123.3(3) . . ?
C22 C21 C20 117.6(2) . . ?
C22 C21 C30 121.7(2) . . ?
C20 C21 C30 120.7(2) . . ?
C21 C22 C23 120.6(2) . . ?
C22 C23 C18 120.1(2) . . ?
C22 C23 C16 133.7(2) . . ?
C18 C23 C16 106.2(2) . . ?
C25 C24 C27 107.0(3) . . ?
C25 C24 C14 112.4(2) . . ?
C27 C24 C14 111.8(2) . . ?
C25 C24 C26 107.6(3) . . ?
C27 C24 C26 109.7(3) . . ?
C14 C24 C26 108.2(2) . . ?
N3 C28 C29 113.0(3) . . ?
C31 C30 C33 107.0(3) . . ?
C31 C30 C32 108.0(3) . . ?
C33 C30 C32 108.4(3) . . ?
C31 C30 C21 112.1(2) . . ?
C33 C30 C21 111.8(2) . . ?
C32 C30 C21 109.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 B1 N1 C1 71.4(4) . . . . ?
F1 B1 N1 C1 -50.1(4) . . . . ?
N2 B1 N1 C1 -169.4(3) . . . . ?
F2 B1 N1 C4 -104.9(3) . . . . ?
F1 B1 N1 C4 133.6(3) . . . . ?
N2 B1 N1 C4 14.4(4) . . . . ?
F2 B1 N2 C9 -65.9(4) . . . . ?
F1 B1 N2 C9 55.2(4) . . . . ?
N1 B1 N2 C9 174.2(3) . . . . ?
F2 B1 N2 C6 105.4(3) . . . . ?
F1 B1 N2 C6 -133.4(3) . . . . ?
N1 B1 N2 C6 -14.5(4) . . . . ?
C4 N1 C1 C2 -0.5(4) . . . . ?
B1 N1 C1 C2 -177.3(3) . . . . ?
N1 C1 C2 C3 1.2(4) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C1 N1 C4 C3 -0.3(3) . . . . ?
B1 N1 C4 C3 176.5(3) . . . . ?
C1 N1 C4 C5 174.4(3) . . . . ?
B1 N1 C4 C5 -8.7(4) . . . . ?
C2 C3 C4 N1 1.1(4) . . . . ?
C2 C3 C4 C5 -172.9(3) . . . . ?
N1 C4 C5 C6 0.5(4) . . . . ?
C3 C4 C5 C6 173.8(3) . . . . ?
N1 C4 C5 C10 -178.9(2) . . . . ?
C3 C4 C5 C10 -5.5(5) . . . . ?
C4 C5 C6 N2 -0.5(4) . . . . ?
C10 C5 C6 N2 178.8(2) . . . . ?
C4 C5 C6 C7 -178.4(3) . . . . ?
C10 C5 C6 C7 0.9(5) . . . . ?
C9 N2 C6 C5 -178.2(3) . . . . ?
B1 N2 C6 C5 9.0(4) . . . . ?
C9 N2 C6 C7 0.1(3) . . . . ?
B1 N2 C6 C7 -172.7(3) . . . . ?
C5 C6 C7 C8 177.5(3) . . . . ?
N2 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C6 N2 C9 C8 0.4(4) . . . . ?
B1 N2 C9 C8 173.0(3) . . . . ?
C7 C8 C9 N2 -0.7(4) . . . . ?
C6 C5 C10 C11 -129(25) . . . . ?
C4 C5 C10 C11 51(25) . . . . ?
C5 C10 C11 C12 -93(25) . . . . ?
C10 C11 C12 C13 17(3) . . . . ?
C10 C11 C12 C17 -158(3) . . . . ?
C17 C12 C13 C14 0.9(4) . . . . ?
C11 C12 C13 C14 -175.3(2) . . . . ?
C12 C13 C14 C15 1.4(4) . . . . ?
C12 C13 C14 C24 179.7(2) . . . . ?
C13 C14 C15 C16 -2.5(4) . . . . ?
C24 C14 C15 C16 179.2(2) . . . . ?
C14 C15 C16 C17 1.3(4) . . . . ?
C14 C15 C16 C23 -175.8(3) . . . . ?
C18 N3 C17 C12 -177.3(3) . . . . ?
C28 N3 C17 C12 -17.0(4) . . . . ?
C18 N3 C17 C16 1.9(3) . . . . ?
C28 N3 C17 C16 162.1(2) . . . . ?
C13 C12 C17 N3 177.0(3) . . . . ?
C11 C12 C17 N3 -7.2(4) . . . . ?
C13 C12 C17 C16 -2.1(4) . . . . ?
C11 C12 C17 C16 173.7(3) . . . . ?
C15 C16 C17 N3 -178.2(2) . . . . ?
C23 C16 C17 N3 -0.4(3) . . . . ?
C15 C16 C17 C12 1.1(4) . . . . ?
C23 C16 C17 C12 178.8(2) . . . . ?
C17 N3 C18 C19 176.7(3) . . . . ?
C28 N3 C18 C19 16.0(4) . . . . ?
C17 N3 C18 C23 -2.7(3) . . . . ?
C28 N3 C18 C23 -163.4(3) . . . . ?
N3 C18 C19 C20 -179.7(3) . . . . ?
C23 C18 C19 C20 -0.4(4) . . . . ?
C18 C19 C20 C21 -0.3(5) . . . . ?
C19 C20 C21 C22 0.4(4) . . . . ?
C19 C20 C21 C30 -179.3(3) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C30 C21 C22 C23 179.8(3) . . . . ?
C21 C22 C23 C18 -0.7(4) . . . . ?
C21 C22 C23 C16 176.6(3) . . . . ?
C19 C18 C23 C22 0.9(4) . . . . ?
N3 C18 C23 C22 -179.7(2) . . . . ?
C19 C18 C23 C16 -177.1(3) . . . . ?
N3 C18 C23 C16 2.4(3) . . . . ?
C15 C16 C23 C22 -1.3(5) . . . . ?
C17 C16 C23 C22 -178.8(3) . . . . ?
C15 C16 C23 C18 176.3(3) . . . . ?
C17 C16 C23 C18 -1.2(3) . . . . ?
C15 C14 C24 C25 -147.1(3) . . . . ?
C13 C14 C24 C25 34.7(4) . . . . ?
C15 C14 C24 C27 -26.8(4) . . . . ?
C13 C14 C24 C27 155.0(3) . . . . ?
C15 C14 C24 C26 94.2(3) . . . . ?
C13 C14 C24 C26 -84.0(3) . . . . ?
C17 N3 C28 C29 -68.0(4) . . . . ?
C18 N3 C28 C29 89.3(3) . . . . ?
C22 C21 C30 C31 28.6(4) . . . . ?
C20 C21 C30 C31 -151.7(4) . . . . ?
C22 C21 C30 C33 148.8(3) . . . . ?
C20 C21 C30 C33 -31.5(4) . . . . ?
C22 C21 C30 C32 -91.2(4) . . . . ?
C20 C21 C30 C32 88.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 994993'
#######################################################################
#
#                 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_rm126

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 B F2 N3'
_chemical_formula_weight         409.23

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   5.5240(3)
_cell_length_b                   13.3635(8)
_cell_length_c                   27.7672(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2049.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5752
_cell_measurement_theta_min      3.9650
_cell_measurement_theta_max      30.3950

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12564
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3620
_reflns_number_gt                2995
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0585P)²+0.2116P] 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     SHELXL
_refine_ls_extinction_coef       0.0104(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(13)
_refine_ls_number_reflns         3620
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
B1 B 0.2005(6) 0.8919(3) 0.67841(11) 0.0560(9) Uani 1 1 d . . .
F1 F 0.0705(4) 0.97369(16) 0.66143(7) 0.0860(7) Uani 1 1 d . . .
F2 F 0.3264(3) 0.84781(17) 0.64099(6) 0.0777(6) Uani 1 1 d . . .
N1 N 0.0300(4) 0.81450(18) 0.70238(7) 0.0501(6) Uani 1 1 d . . .
N2 N 0.3786(4) 0.92606(17) 0.71823(7) 0.0491(6) Uani 1 1 d . . .
N3 N 0.1342(4) 0.49128(17) 0.99608(7) 0.0526(6) Uani 1 1 d . . .
C1 C -0.1666(5) 0.7715(3) 0.68274(11) 0.0627(8) Uani 1 1 d . . .
H1 H -0.2296 0.7868 0.6518 0.075 Uiso 1 1 calc R . .
C2 C -0.2652(5) 0.7011(3) 0.71441(11) 0.0638(8) Uani 1 1 d . . .
H2 H -0.4044 0.6609 0.7090 0.077 Uiso 1 1 calc R . .
C3 C -0.1225(5) 0.7014(2) 0.75454(11) 0.0560(7) Uani 1 1 d . . .
H3 H -0.1442 0.6607 0.7823 0.067 Uiso 1 1 calc R . .
C4 C 0.0622(5) 0.7725(2) 0.74776(9) 0.0471(6) Uani 1 1 d . . .
C5 C 0.2465(5) 0.8056(2) 0.77789(8) 0.0446(6) Uani 1 1 d . . .
C6 C 0.4004(5) 0.8838(2) 0.76367(9) 0.0458(6) Uani 1 1 d . . .
C7 C 0.5971(5) 0.9288(2) 0.78751(11) 0.0577(7) Uani 1 1 d . . .
H7 H 0.6533 0.9139 0.8190 0.069 Uiso 1 1 calc R . .
C8 C 0.6922(6) 0.9985(2) 0.75640(12) 0.0676(8) Uani 1 1 d . . .
H8 H 0.8263 1.0411 0.7625 0.081 Uiso 1 1 calc R . .
C9 C 0.5565(6) 0.9949(2) 0.71454(12) 0.0640(8) Uani 1 1 d . . .
H9 H 0.5846 1.0354 0.6870 0.077 Uiso 1 1 calc R . .
C10 C 0.2826(5) 0.7602(2) 0.82377(9) 0.0504(7) Uani 1 1 d . . .
C11 C 0.3245(5) 0.7207(2) 0.86167(9) 0.0502(7) Uani 1 1 d . . .
C12 C 0.3702(5) 0.6762(2) 0.90766(9) 0.0486(6) Uani 1 1 d . . .
C13 C 0.2162(5) 0.6019(2) 0.92482(9) 0.0479(7) Uani 1 1 d . . .
H13 H 0.0842 0.5784 0.9060 0.057 Uiso 1 1 calc R . .
C14 C 0.2622(5) 0.56312(19) 0.97044(9) 0.0441(6) Uani 1 1 d . . .
C15 C 0.4587(5) 0.5973(2) 0.99864(9) 0.0456(6) Uani 1 1 d . . .
C16 C 0.6131(5) 0.6703(2) 0.98027(10) 0.0544(7) Uani 1 1 d . . .
H16 H 0.7474 0.6930 0.9986 0.065 Uiso 1 1 calc R . .
C17 C 0.5689(5) 0.7095(2) 0.93496(10) 0.0550(7) Uani 1 1 d . . .
H17 H 0.6736 0.7593 0.9222 0.066 Uiso 1 1 calc R . .
C18 C 0.4493(5) 0.5432(2) 1.04335(9) 0.0472(6) Uani 1 1 d . . .
C19 C 0.5938(6) 0.5424(2) 1.08478(9) 0.0619(8) Uani 1 1 d . . .
H19 H 0.7291 0.5859 1.0875 0.074 Uiso 1 1 calc R . .
C20 C 0.5356(7) 0.4771(3) 1.12156(10) 0.0682(9) Uani 1 1 d . . .
H20 H 0.6320 0.4760 1.1499 0.082 Uiso 1 1 calc R . .
C21 C 0.3397(7) 0.4134(3) 1.11785(10) 0.0683(9) Uani 1 1 d . . .
H21 H 0.3043 0.3695 1.1438 0.082 Uiso 1 1 calc R . .
C22 C 0.1941(6) 0.4117(2) 1.07752(9) 0.0577(8) Uani 1 1 d . . .
H22 H 0.0602 0.3673 1.0752 0.069 Uiso 1 1 calc R . .
C23 C 0.2510(5) 0.4776(2) 1.04023(9) 0.0473(6) Uani 1 1 d . . .
C24 C -0.0422(6) 0.4224(2) 0.97569(11) 0.0627(8) Uani 1 1 d . . .
H24A H -0.1316 0.4564 0.9495 0.075 Uiso 1 1 calc R . .
H24B H -0.1606 0.4034 1.0009 0.075 Uiso 1 1 calc R . .
C25 C 0.0759(8) 0.3302(3) 0.95631(13) 0.0895(12) Uani 1 1 d . . .
H25A H 0.1989 0.3491 0.9325 0.134 Uiso 1 1 calc R . .
H25B H -0.0463 0.2878 0.9409 0.134 Uiso 1 1 calc R . .
H25C H 0.1527 0.2934 0.9827 0.134 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
B1 F2 1.382(4) . ?
B1 F1 1.390(4) . ?
B1 N2 1.549(4) . ?
B1 N1 1.549(4) . ?
N1 C1 1.344(4) . ?
N1 C4 1.391(3) . ?
N2 C9 1.350(4) . ?
N2 C6 1.388(3) . ?
N3 C14 1.389(3) . ?
N3 C23 1.397(3) . ?
N3 C24 1.455(3) . ?
C1 C2 1.398(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.365(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.407(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(4) . ?
C5 C6 1.403(4) . ?
C5 C10 1.425(3) . ?
C6 C7 1.407(4) . ?
C7 C8 1.375(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.200(3) . ?
C11 C12 1.431(3) . ?
C12 C13 1.392(4) . ?
C12 C17 1.406(4) . ?
C13 C14 1.392(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.414(4) . ?
C15 C16 1.392(4) . ?
C15 C18 1.438(3) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.400(4) . ?
C18 C23 1.406(4) . ?
C19 C20 1.381(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.396(4) . ?
C22 H22 0.9500 . ?
C24 C25 1.494(5) . ?
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
F2 B1 F1 109.9(2) . . ?
F2 B1 N2 110.0(2) . . ?
F1 B1 N2 109.8(3) . . ?
F2 B1 N1 110.1(3) . . ?
F1 B1 N1 110.9(3) . . ?
N2 B1 N1 106.0(2) . . ?
C1 N1 C4 107.4(3) . . ?
C1 N1 B1 127.0(2) . . ?
C4 N1 B1 125.5(2) . . ?
C9 N2 C6 106.5(2) . . ?
C9 N2 B1 127.5(2) . . ?
C6 N2 B1 125.7(2) . . ?
C14 N3 C23 107.7(2) . . ?
C14 N3 C24 125.4(2) . . ?
C23 N3 C24 124.6(2) . . ?
N1 C1 C2 110.3(3) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C3 C2 C1 106.6(3) . . ?
C3 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C2 C3 C4 108.2(3) . . ?
C2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
C5 C4 N1 120.7(2) . . ?
C5 C4 C3 131.7(2) . . ?
N1 C4 C3 107.5(2) . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 C10 120.3(3) . . ?
C6 C5 C10 118.9(2) . . ?
N2 C6 C5 120.4(2) . . ?
N2 C6 C7 108.7(2) . . ?
C5 C6 C7 130.8(2) . . ?
C8 C7 C6 106.8(3) . . ?
C8 C7 H7 126.6 . . ?
C6 C7 H7 126.6 . . ?
C7 C8 C9 107.3(3) . . ?
C7 C8 H8 126.3 . . ?
C9 C8 H8 126.3 . . ?
N2 C9 C8 110.7(3) . . ?
N2 C9 H9 124.6 . . ?
C8 C9 H9 124.6 . . ?
C11 C10 C5 176.7(3) . . ?
C10 C11 C12 178.1(3) . . ?
C13 C12 C17 121.2(2) . . ?
C13 C12 C11 119.6(2) . . ?
C17 C12 C11 119.2(3) . . ?
C14 C13 C12 117.7(3) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
N3 C14 C13 129.1(2) . . ?
N3 C14 C15 109.3(2) . . ?
C13 C14 C15 121.6(2) . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 C18 133.7(3) . . ?
C14 C15 C18 106.7(2) . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 120.5(3) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C19 C18 C23 119.3(3) . . ?
C19 C18 C15 133.9(3) . . ?
C23 C18 C15 106.8(2) . . ?
C20 C19 C18 118.7(3) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 121.1(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 121.9(3) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23 117.4(3) . . ?
C21 C22 H22 121.3 . . ?
C23 C22 H22 121.3 . . ?
C22 C23 N3 129.0(3) . . ?
C22 C23 C18 121.6(2) . . ?
N3 C23 C18 109.4(2) . . ?
N3 C24 C25 111.6(3) . . ?
N3 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
N3 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 . . ?

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
F2 B1 N1 C1 -67.4(4) . . . . ?
F1 B1 N1 C1 54.4(4) . . . . ?
N2 B1 N1 C1 173.6(2) . . . . ?
F2 B1 N1 C4 108.7(3) . . . . ?
F1 B1 N1 C4 -129.5(3) . . . . ?
N2 B1 N1 C4 -10.4(4) . . . . ?
F2 B1 N2 C9 62.8(4) . . . . ?
F1 B1 N2 C9 -58.3(4) . . . . ?
N1 B1 N2 C9 -178.2(2) . . . . ?
F2 B1 N2 C6 -110.4(3) . . . . ?
F1 B1 N2 C6 128.5(3) . . . . ?
N1 B1 N2 C6 8.7(4) . . . . ?
C4 N1 C1 C2 -0.2(3) . . . . ?
B1 N1 C1 C2 176.4(3) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 N1 C4 C5 -177.0(2) . . . . ?
B1 N1 C4 C5 6.2(4) . . . . ?
C1 N1 C4 C3 0.5(3) . . . . ?
B1 N1 C4 C3 -176.2(2) . . . . ?
C2 C3 C4 C5 176.6(3) . . . . ?
C2 C3 C4 N1 -0.6(3) . . . . ?
N1 C4 C5 C6 1.5(4) . . . . ?
C3 C4 C5 C6 -175.4(3) . . . . ?
N1 C4 C5 C10 -178.2(2) . . . . ?
C3 C4 C5 C10 4.9(4) . . . . ?
C9 N2 C6 C5 -177.2(2) . . . . ?
B1 N2 C6 C5 -2.8(4) . . . . ?
C9 N2 C6 C7 -0.1(3) . . . . ?
B1 N2 C6 C7 174.2(2) . . . . ?
C4 C5 C6 N2 -3.2(4) . . . . ?
C10 C5 C6 N2 176.5(2) . . . . ?
C4 C5 C6 C7 -179.5(3) . . . . ?
C10 C5 C6 C7 0.2(4) . . . . ?
N2 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C7 C8 177.0(3) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C6 N2 C9 C8 -0.1(3) . . . . ?
B1 N2 C9 C8 -174.4(3) . . . . ?
C7 C8 C9 N2 0.4(4) . . . . ?
C4 C5 C10 C11 121(5) . . . . ?
C6 C5 C10 C11 -59(5) . . . . ?
C5 C10 C11 C12 140(8) . . . . ?
C10 C11 C12 C13 95(10) . . . . ?
C10 C11 C12 C17 -84(10) . . . . ?
C17 C12 C13 C14 1.4(4) . . . . ?
C11 C12 C13 C14 -177.8(2) . . . . ?
C23 N3 C14 C13 -179.9(3) . . . . ?
C24 N3 C14 C13 16.7(4) . . . . ?
C23 N3 C14 C15 -1.3(3) . . . . ?
C24 N3 C14 C15 -164.8(2) . . . . ?
C12 C13 C14 N3 178.2(3) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
N3 C14 C15 C16 -179.8(2) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
N3 C14 C15 C18 0.2(3) . . . . ?
C13 C14 C15 C18 178.9(2) . . . . ?
C14 C15 C16 C17 1.2(4) . . . . ?
C18 C15 C16 C17 -178.9(3) . . . . ?
C15 C16 C17 C12 0.0(4) . . . . ?
C13 C12 C17 C16 -1.4(4) . . . . ?
C11 C12 C17 C16 177.8(3) . . . . ?
C16 C15 C18 C19 -1.3(5) . . . . ?
C14 C15 C18 C19 178.7(3) . . . . ?
C16 C15 C18 C23 -179.1(3) . . . . ?
C14 C15 C18 C23 0.9(3) . . . . ?
C23 C18 C19 C20 -0.3(4) . . . . ?
C15 C18 C19 C20 -177.9(3) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C19 C20 C21 C22 0.2(5) . . . . ?
C20 C21 C22 C23 -0.3(5) . . . . ?
C21 C22 C23 N3 -179.7(3) . . . . ?
C21 C22 C23 C18 0.2(4) . . . . ?
C14 N3 C23 C22 -178.2(3) . . . . ?
C24 N3 C23 C22 -14.6(4) . . . . ?
C14 N3 C23 C18 1.9(3) . . . . ?
C24 N3 C23 C18 165.5(2) . . . . ?
C19 C18 C23 C22 0.1(4) . . . . ?
C15 C18 C23 C22 178.3(2) . . . . ?
C19 C18 C23 N3 -179.9(3) . . . . ?
C15 C18 C23 N3 -1.8(3) . . . . ?
C14 N3 C24 C25 86.2(3) . . . . ?
C23 N3 C24 C25 -74.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 994994'
#######################################################################
#
#                 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_rm116

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 B F2 N3'
_chemical_formula_weight         409.23

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c n'

loop_
_symmetry_equiv_pos_as_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'
'-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                   30.9020(9)
_cell_length_b                   8.2967(2)
_cell_length_c                   15.5348(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3982.88(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10410
_cell_measurement_theta_min      3.6480
_cell_measurement_theta_max      30.6720

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_min  0.9697
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            52570
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         32.19
_reflns_number_total             6770
_reflns_number_gt                4575
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0580P)²+1.3868P] 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         6770
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
B1 B 0.67550(5) 0.3705(2) 0.69029(11) 0.0273(3) Uani 1 1 d . . .
F1 F 0.69898(3) 0.47126(12) 0.63587(7) 0.0400(3) Uani 1 1 d . . .
F2 F 0.69520(3) 0.36411(13) 0.77032(7) 0.0432(3) Uani 1 1 d . . .
N1 N 0.62836(4) 0.43250(14) 0.69896(8) 0.0230(2) Uani 1 1 d . . .
N2 N 0.67242(4) 0.19872(15) 0.65137(8) 0.0260(3) Uani 1 1 d . . .
N3 N 0.38255(4) -0.37122(13) 0.54023(8) 0.0217(2) Uani 1 1 d . . .
C1 C 0.61577(5) 0.58194(19) 0.72386(10) 0.0306(3) Uani 1 1 d . . .
H1 H 0.6348 0.6671 0.7391 0.037 Uiso 1 1 calc R . .
C2 C 0.57069(6) 0.5922(2) 0.72378(10) 0.0348(4) Uani 1 1 d . . .
H2 H 0.5539 0.6841 0.7384 0.042 Uiso 1 1 calc R . .
C3 C 0.55504(5) 0.4429(2) 0.69827(10) 0.0296(3) Uani 1 1 d . . .
H3 H 0.5255 0.4133 0.6921 0.036 Uiso 1 1 calc R . .
C4 C 0.59115(4) 0.34354(17) 0.68322(9) 0.0224(3) Uani 1 1 d . . .
C5 C 0.59392(4) 0.18258(17) 0.65366(9) 0.0217(3) Uani 1 1 d . . .
C6 C 0.63430(5) 0.11306(18) 0.63714(9) 0.0244(3) Uani 1 1 d . . .
C7 C 0.64557(6) -0.0417(2) 0.60547(11) 0.0356(4) Uani 1 1 d . . .
H7 H 0.6261 -0.1256 0.5903 0.043 Uiso 1 1 calc R . .
C8 C 0.69014(6) -0.0472(2) 0.60084(13) 0.0452(5) Uani 1 1 d . . .
H8 H 0.7071 -0.1355 0.5816 0.054 Uiso 1 1 calc R . .
C9 C 0.70562(5) 0.1024(2) 0.62999(12) 0.0386(4) Uani 1 1 d . . .
H9 H 0.7353 0.1312 0.6340 0.046 Uiso 1 1 calc R . .
C10 C 0.55578(5) 0.09091(19) 0.63993(10) 0.0272(3) Uani 1 1 d . . .
C11 C 0.52385(5) 0.01129(18) 0.62633(10) 0.0274(3) Uani 1 1 d . . .
C12 C 0.48783(4) -0.08961(18) 0.60547(10) 0.0254(3) Uani 1 1 d . . .
C13 C 0.49602(5) -0.23694(18) 0.56245(10) 0.0282(3) Uani 1 1 d . . .
H13 H 0.5250 -0.2664 0.5498 0.034 Uiso 1 1 calc R . .
C14 C 0.46287(4) -0.33863(17) 0.53848(10) 0.0255(3) Uani 1 1 d . . .
H14 H 0.4686 -0.4375 0.5098 0.031 Uiso 1 1 calc R . .
C15 C 0.42054(4) -0.29117(16) 0.55776(9) 0.0207(3) Uani 1 1 d . . .
C16 C 0.41128(4) -0.14397(16) 0.60093(9) 0.0204(3) Uani 1 1 d . . .
C17 C 0.44528(4) -0.04310(17) 0.62491(9) 0.0232(3) Uani 1 1 d . . .
H17 H 0.4397 0.0555 0.6539 0.028 Uiso 1 1 calc R . .
C18 C 0.36464(4) -0.13840(16) 0.61096(9) 0.0208(3) Uani 1 1 d . . .
C19 C 0.33614(5) -0.02995(17) 0.65042(9) 0.0253(3) Uani 1 1 d . . .
H19 H 0.3467 0.0657 0.6767 0.030 Uiso 1 1 calc R . .
C20 C 0.29230(5) -0.06496(19) 0.65041(11) 0.0310(3) Uani 1 1 d . . .
H20 H 0.2726 0.0073 0.6772 0.037 Uiso 1 1 calc R . .
C21 C 0.27656(5) -0.2054(2) 0.61138(11) 0.0322(3) Uani 1 1 d . . .
H21 H 0.2463 -0.2256 0.6116 0.039 Uiso 1 1 calc R . .
C22 C 0.30403(5) -0.31614(18) 0.57240(10) 0.0275(3) Uani 1 1 d . . .
H22 H 0.2932 -0.4116 0.5464 0.033 Uiso 1 1 calc R . .
C23 C 0.34828(4) -0.28091(16) 0.57313(9) 0.0211(3) Uani 1 1 d . . .
C24 C 0.38008(5) -0.53621(16) 0.50773(9) 0.0240(3) Uani 1 1 d . . .
H24A H 0.4013 -0.5499 0.4605 0.029 Uiso 1 1 calc R . .
H24B H 0.3509 -0.5555 0.4838 0.029 Uiso 1 1 calc R . .
C25 C 0.38919(7) -0.65983(18) 0.57764(11) 0.0387(4) Uani 1 1 d . . .
H25A H 0.4176 -0.6384 0.6033 0.058 Uiso 1 1 calc R . .
H25B H 0.3890 -0.7682 0.5525 0.058 Uiso 1 1 calc R . .
H25C H 0.3668 -0.6526 0.6222 0.058 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
B1 F2 1.3854(19) . ?
B1 F1 1.3926(19) . ?
B1 N1 1.551(2) . ?
B1 N2 1.551(2) . ?
N1 C1 1.3557(19) . ?
N1 C4 1.3879(17) . ?
N2 C9 1.342(2) . ?
N2 C6 1.3934(18) . ?
N3 C15 1.3759(17) . ?
N3 C23 1.3943(17) . ?
N3 C24 1.4611(17) . ?
C1 C2 1.396(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.4067(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.415(2) . ?
C5 C6 1.3985(19) . ?
C5 C10 1.4190(19) . ?
C6 C7 1.418(2) . ?
C7 C8 1.380(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.405(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.206(2) . ?
C11 C12 1.430(2) . ?
C12 C17 1.403(2) . ?
C12 C13 1.416(2) . ?
C13 C14 1.378(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3985(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.4224(19) . ?
C16 C17 1.3939(19) . ?
C16 C18 1.4504(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.4002(19) . ?
C18 C23 1.4138(19) . ?
C19 C20 1.386(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.401(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.3983(19) . ?
C22 H22 0.9500 . ?
C24 C25 1.520(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
F2 B1 F1 109.81(12) . . ?
F2 B1 N1 110.34(13) . . ?
F1 B1 N1 110.08(13) . . ?
F2 B1 N2 109.96(13) . . ?
F1 B1 N2 110.30(13) . . ?
N1 B1 N2 106.31(11) . . ?
C1 N1 C4 107.40(12) . . ?
C1 N1 B1 126.68(13) . . ?
C4 N1 B1 125.92(12) . . ?
C9 N2 C6 107.64(14) . . ?
C9 N2 B1 126.63(14) . . ?
C6 N2 B1 125.62(12) . . ?
C15 N3 C23 108.43(11) . . ?
C15 N3 C24 124.42(11) . . ?
C23 N3 C24 126.19(11) . . ?
N1 C1 C2 109.98(14) . . ?
N1 C1 H1 125.0 . . ?
C2 C1 H1 125.0 . . ?
C3 C2 C1 107.08(14) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
C2 C3 C4 107.09(13) . . ?
C2 C3 H3 126.5 . . ?
C4 C3 H3 126.5 . . ?
N1 C4 C3 108.44(13) . . ?
N1 C4 C5 120.59(12) . . ?
C3 C4 C5 130.91(13) . . ?
C6 C5 C4 120.19(12) . . ?
C6 C5 C10 119.51(13) . . ?
C4 C5 C10 120.29(13) . . ?
N2 C6 C5 120.98(13) . . ?
N2 C6 C7 108.02(13) . . ?
C5 C6 C7 131.00(14) . . ?
C8 C7 C6 107.06(15) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
C7 C8 C9 107.06(15) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 110.21(15) . . ?
N2 C9 H9 124.9 . . ?
C8 C9 H9 124.9 . . ?
C11 C10 C5 178.27(17) . . ?
C10 C11 C12 175.69(17) . . ?
C17 C12 C13 120.42(13) . . ?
C17 C12 C11 121.31(14) . . ?
C13 C12 C11 118.25(13) . . ?
C14 C13 C12 121.55(13) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 117.70(13) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
N3 C15 C14 128.30(13) . . ?
N3 C15 C16 109.63(11) . . ?
C14 C15 C16 122.07(12) . . ?
C17 C16 C15 119.33(12) . . ?
C17 C16 C18 134.52(13) . . ?
C15 C16 C18 106.15(11) . . ?
C16 C17 C12 118.93(13) . . ?
C16 C17 H17 120.5 . . ?
C12 C17 H17 120.5 . . ?
C19 C18 C23 119.64(12) . . ?
C19 C18 C16 133.82(13) . . ?
C23 C18 C16 106.49(11) . . ?
C20 C19 C18 118.69(13) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 120.92(14) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 121.76(14) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23 117.12(14) . . ?
C21 C22 H22 121.4 . . ?
C23 C22 H22 121.4 . . ?
N3 C23 C22 128.86(13) . . ?
N3 C23 C18 109.28(11) . . ?
C22 C23 C18 121.85(13) . . ?
N3 C24 C25 112.06(12) . . ?
N3 C24 H24A 109.2 . . ?
C25 C24 H24A 109.2 . . ?
N3 C24 H24B 109.2 . . ?
C25 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
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 . . ?

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
F2 B1 N1 C1 66.28(19) . . . . ?
F1 B1 N1 C1 -55.07(19) . . . . ?
N2 B1 N1 C1 -174.52(13) . . . . ?
F2 B1 N1 C4 -113.09(15) . . . . ?
F1 B1 N1 C4 125.56(14) . . . . ?
N2 B1 N1 C4 6.10(19) . . . . ?
F2 B1 N2 C9 -63.2(2) . . . . ?
F1 B1 N2 C9 58.1(2) . . . . ?
N1 B1 N2 C9 177.38(14) . . . . ?
F2 B1 N2 C6 112.75(15) . . . . ?
F1 B1 N2 C6 -126.01(14) . . . . ?
N1 B1 N2 C6 -6.69(19) . . . . ?
C4 N1 C1 C2 -0.57(17) . . . . ?
B1 N1 C1 C2 179.96(13) . . . . ?
N1 C1 C2 C3 0.33(18) . . . . ?
C1 C2 C3 C4 0.03(17) . . . . ?
C1 N1 C4 C3 0.58(16) . . . . ?
B1 N1 C4 C3 -179.94(13) . . . . ?
C1 N1 C4 C5 178.24(13) . . . . ?
B1 N1 C4 C5 -2.3(2) . . . . ?
C2 C3 C4 N1 -0.38(17) . . . . ?
C2 C3 C4 C5 -177.71(15) . . . . ?
N1 C4 C5 C6 -2.2(2) . . . . ?
C3 C4 C5 C6 174.86(14) . . . . ?
N1 C4 C5 C10 178.28(13) . . . . ?
C3 C4 C5 C10 -4.7(2) . . . . ?
C9 N2 C6 C5 -179.95(14) . . . . ?
B1 N2 C6 C5 3.5(2) . . . . ?
C9 N2 C6 C7 -0.19(17) . . . . ?
B1 N2 C6 C7 -176.76(14) . . . . ?
C4 C5 C6 N2 1.6(2) . . . . ?
C10 C5 C6 N2 -178.86(13) . . . . ?
C4 C5 C6 C7 -178.08(15) . . . . ?
C10 C5 C6 C7 1.4(2) . . . . ?
N2 C6 C7 C8 -0.13(18) . . . . ?
C5 C6 C7 C8 179.60(16) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C6 N2 C9 C8 0.43(19) . . . . ?
B1 N2 C9 C8 176.96(15) . . . . ?
C7 C8 C9 N2 -0.5(2) . . . . ?
C6 C5 C10 C11 -39(6) . . . . ?
C4 C5 C10 C11 140(6) . . . . ?
C5 C10 C11 C12 12(7) . . . . ?
C10 C11 C12 C17 -160(2) . . . . ?
C10 C11 C12 C13 19(2) . . . . ?
C17 C12 C13 C14 0.0(2) . . . . ?
C11 C12 C13 C14 -178.47(14) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C23 N3 C15 C14 178.49(14) . . . . ?
C24 N3 C15 C14 9.2(2) . . . . ?
C23 N3 C15 C16 -1.46(15) . . . . ?
C24 N3 C15 C16 -170.78(12) . . . . ?
C13 C14 C15 N3 179.76(14) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
N3 C15 C16 C17 -179.98(12) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
N3 C15 C16 C18 1.13(15) . . . . ?
C14 C15 C16 C18 -178.82(13) . . . . ?
C15 C16 C17 C12 0.2(2) . . . . ?
C18 C16 C17 C12 178.69(14) . . . . ?
C13 C12 C17 C16 -0.2(2) . . . . ?
C11 C12 C17 C16 178.18(13) . . . . ?
C17 C16 C18 C19 -1.5(3) . . . . ?
C15 C16 C18 C19 177.10(15) . . . . ?
C17 C16 C18 C23 -179.01(15) . . . . ?
C15 C16 C18 C23 -0.37(14) . . . . ?
C23 C18 C19 C20 -0.7(2) . . . . ?
C16 C18 C19 C20 -177.92(15) . . . . ?
C18 C19 C20 C21 -0.3(2) . . . . ?
C19 C20 C21 C22 1.0(3) . . . . ?
C20 C21 C22 C23 -0.5(2) . . . . ?
C15 N3 C23 C22 -178.36(14) . . . . ?
C24 N3 C23 C22 -9.3(2) . . . . ?
C15 N3 C23 C18 1.22(15) . . . . ?
C24 N3 C23 C18 170.30(12) . . . . ?
C21 C22 C23 N3 178.92(14) . . . . ?
C21 C22 C23 C18 -0.6(2) . . . . ?
C19 C18 C23 N3 -178.41(12) . . . . ?
C16 C18 C23 N3 -0.50(15) . . . . ?
C19 C18 C23 C22 1.2(2) . . . . ?
C16 C18 C23 C22 179.11(13) . . . . ?
C15 N3 C24 C25 75.92(17) . . . . ?
C23 N3 C24 C25 -91.50(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 994991'
