# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182

_publ_section_title              
;D-Camphor-derived triazolium salts for catalytic
intramolecular crossed aldehyde-ketone benzoin reactions
;
_publ_contact_author_name        'rof. Shu-Li You'
_publ_contact_author_email       SLYOU@MAIL.SIOC.AC.CN
loop_
_publ_author_name
'Shu-Li You'
'Zhen Feng'
'Yi Li'

# Attachment 'cd27300.cif.pdf'

data_cd27300
_database_code_depnum_ccdc_archive 'CCDC 671038'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 B F4 N3 O'
_chemical_formula_weight         439.30

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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   12.0906(18)
_cell_length_b                   7.9338(12)
_cell_length_c                   13.540(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.257(2)
_cell_angle_gamma                90.00
_cell_volume                     1164.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1849
_cell_measurement_theta_min      6.044
_cell_measurement_theta_max      47.389

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.497
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.181
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.75123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6146
_diffrn_reflns_av_R_equivalents  0.1465
_diffrn_reflns_av_sigmaI/netI    0.1135
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2332
_reflns_number_gt                1571
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR
and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc.
and is
not relevant to the choice of reflections for refinement. R-factors
based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0828P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.010(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2332
_refine_ls_number_parameters     287
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1626
_refine_ls_wR_factor_gt          0.1517
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.002

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
O1 O 0.1667(3) 0.2603(5) 1.1270(2) 0.0832(11) Uani 1 1 d . . .
N1 N 0.1872(3) 0.4759(5) 0.8405(2) 0.0624(9) Uani 1 1 d . . .
N2 N 0.0998(3) 0.3758(6) 0.8514(2) 0.0758(12) Uani 1 1 d . . .
N3 N 0.2703(3) 0.3902(4) 1.0064(2) 0.0548(9) Uani 1 1 d . . .
F1 F 0.4256(5) 0.8137(6) 0.9594(4) 0.1508(17) Uani 1 1 d . . .
F2 F 0.2994(3) 0.8389(6) 1.0357(3) 0.1231(13) Uani 1 1 d . . .
F3 F 0.4804(3) 0.9783(5) 1.1100(3) 0.1163(11) Uani 1 1 d . . .
F4 F 0.3285(5) 1.0561(5) 0.9488(3) 0.1419(17) Uani 1 1 d . . .
B1 B 0.3835(7) 0.9245(7) 1.0098(6) 0.0792(16) Uani 1 1 d . . .
C1 C 0.2896(3) 0.4830(6) 0.9338(3) 0.0536(9) Uani 1 1 d . . .
H1 H 0.3611 0.5416 0.9462 0.064 Uiso 1 1 calc R . .
C2 C 0.1554(4) 0.3248(7) 0.9542(3) 0.0681(12) Uani 1 1 d . . .
C3 C 0.1097(5) 0.2108(9) 1.0148(4) 0.0913(18) Uani 1 1 d . . .
H3A H 0.0208 0.2196 0.9854 0.110 Uiso 1 1 calc R . .
H3B H 0.1305 0.0949 1.0076 0.110 Uiso 1 1 calc R . .
C4 C 0.2977(4) 0.2418(7) 1.1783(3) 0.0690(13) Uani 1 1 d . . .
H4 H 0.3203 0.1222 1.1854 0.083 Uiso 1 1 calc R . .
C5 C 0.3620(4) 0.3396(5) 1.1173(3) 0.0540(10) Uani 1 1 d . . .
H5 H 0.4209 0.2630 1.1089 0.065 Uiso 1 1 calc R . .
C6 C 0.4350(4) 0.4787(7) 1.1972(3) 0.0639(11) Uani 1 1 d . . .
H6 H 0.4528 0.5774 1.1632 0.077 Uiso 1 1 calc R . .
C7 C 0.5480(4) 0.3861(8) 1.2808(3) 0.0825(15) Uani 1 1 d . . .
H7A H 0.6085 0.4640 1.3313 0.099 Uiso 1 1 calc R . .
H7B H 0.5863 0.3181 1.2448 0.099 Uiso 1 1 calc R . .
C8 C 0.4910(4) 0.2742(10) 1.3409(3) 0.0937(18) Uani 1 1 d . . .
H8A H 0.4990 0.1556 1.3280 0.112 Uiso 1 1 calc R . .
H8B H 0.5308 0.2953 1.4196 0.112 Uiso 1 1 calc R . .
C9 C 0.3549(4) 0.3269(9) 1.2903(3) 0.0835(16) Uani 1 1 d . . .
C10 C 0.3602(5) 0.5153(8) 1.2620(3) 0.0814(16) Uani 1 1 d . . .
C11 C 0.2917(5) 0.2771(14) 1.3629(4) 0.117(3) Uani 1 1 d . . .
H11A H 0.2077 0.3153 1.3291 0.131 Uiso 1 1 calc R . .
H11B H 0.3346 0.3283 1.4342 0.131 Uiso 1 1 calc R . .
H11C H 0.2935 0.1568 1.3708 0.131 Uiso 1 1 calc R . .
C12 C 0.4318(7) 0.6257(13) 1.3663(4) 0.111(3) Uani 1 1 d . . .
H12A H 0.4533 0.7314 1.3449 0.132 Uiso 1 1 calc R . .
H12B H 0.5055 0.5680 1.4154 0.132 Uiso 1 1 calc R . .
H12C H 0.3807 0.6456 1.4028 0.132 Uiso 1 1 calc R . .
C13 C 0.2370(5) 0.6073(9) 1.1963(4) 0.0987(19) Uani 1 1 d . . .
H13A H 0.2526 0.7240 1.1886 0.118 Uiso 1 1 calc R . .
H13B H 0.1868 0.5982 1.2346 0.118 Uiso 1 1 calc R . .
H13C H 0.1947 0.5571 1.1247 0.118 Uiso 1 1 calc R . .
C14 C 0.1654(4) 0.5560(6) 0.7379(3) 0.0599(11) Uani 1 1 d . . .
C15 C 0.2041(4) 0.4684(7) 0.6687(3) 0.0682(12) Uani 1 1 d . . .
C16 C 0.1871(4) 0.5553(8) 0.5736(3) 0.0749(14) Uani 1 1 d . . .
H16 H 0.2122 0.5036 0.5253 0.090 Uiso 1 1 calc R . .
C17 C 0.1357(4) 0.7119(9) 0.5473(3) 0.0808(15) Uani 1 1 d . . .
C18 C 0.0963(4) 0.7885(8) 0.6167(3) 0.0751(13) Uani 1 1 d . . .
H18 H 0.0590 0.8939 0.5983 0.090 Uiso 1 1 calc R . .
C19 C 0.1108(4) 0.7118(7) 0.7144(3) 0.0715(13) Uani 1 1 d . . .
C20 C 0.2618(6) 0.2990(8) 0.6958(4) 0.0983(18) Uani 1 1 d . . .
H20A H 0.2895 0.2674 0.6420 0.117 Uiso 1 1 calc R . .
H20B H 0.2024 0.2184 0.6954 0.117 Uiso 1 1 calc R . .
H20C H 0.3308 0.3016 0.7674 0.117 Uiso 1 1 calc R . .
C21 C 0.1239(6) 0.8029(12) 0.4439(4) 0.121(2) Uani 1 1 d . . .
H21A H 0.2026 0.8047 0.4426 0.131 Uiso 1 1 calc R . .
H21B H 0.0964 0.9164 0.4442 0.131 Uiso 1 1 calc R . .
H21C H 0.0652 0.7450 0.3800 0.131 Uiso 1 1 calc R . .
C22 C 0.0671(5) 0.8010(9) 0.7892(4) 0.0974(18) Uani 1 1 d . . .
H22A H 0.0000 0.7392 0.7915 0.116 Uiso 1 1 calc R . .
H22B H 0.0397 0.9125 0.7616 0.116 Uiso 1 1 calc R . .
H22C H 0.1337 0.8082 0.8620 0.116 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0583(18) 0.148(3) 0.0432(14) 0.0012(18) 0.0227(13) -0.0207(19)
N1 0.0481(19) 0.099(2) 0.0359(16) 0.0014(17) 0.0145(14) -0.0088(19)
N2 0.054(2) 0.125(3) 0.0403(18) -0.004(2) 0.0135(16) -0.022(2)
N3 0.0425(17) 0.081(2) 0.0349(15) -0.0052(16) 0.0113(13) -0.0048(16)
F1 0.204(4) 0.108(3) 0.216(4) -0.041(3) 0.161(4) -0.021(3)
F2 0.106(3) 0.157(3) 0.121(3) -0.004(3) 0.064(2) -0.024(3)
F3 0.090(2) 0.113(2) 0.126(3) -0.006(2) 0.030(2) -0.002(2)
F4 0.205(5) 0.094(2) 0.096(2) -0.004(2) 0.039(3) 0.002(3)
B1 0.094(4) 0.057(3) 0.093(4) -0.007(3) 0.047(4) -0.005(3)
C1 0.041(2) 0.078(2) 0.0349(17) -0.0042(19) 0.0113(15) -0.007(2)
C2 0.050(2) 0.110(4) 0.0419(19) -0.011(2) 0.0184(18) -0.019(2)
C3 0.069(3) 0.128(5) 0.053(2) -0.004(3) 0.024(2) -0.039(3)
C4 0.060(3) 0.101(4) 0.048(2) 0.005(2) 0.0256(19) -0.006(2)
C5 0.051(2) 0.072(3) 0.0352(17) 0.0039(18) 0.0152(16) 0.0020(19)
C6 0.055(2) 0.088(3) 0.0341(17) -0.001(2) 0.0074(16) -0.001(2)
C7 0.055(2) 0.128(4) 0.049(2) 0.008(3) 0.0083(19) 0.000(3)
C8 0.070(3) 0.120(5) 0.048(2) 0.032(3) 0.013(2) 0.011(3)
C9 0.064(3) 0.129(5) 0.0344(19) 0.007(3) 0.0185(19) -0.002(3)
C10 0.077(3) 0.115(5) 0.045(2) -0.021(3) 0.021(2) 0.006(3)
C11 0.080(4) 0.140(9) 0.044(2) 0.016(4) 0.031(2) -0.006(5)
C12 0.107(6) 0.147(9) 0.068(3) -0.066(5) 0.033(4) -0.002(6)
C13 0.093(4) 0.126(5) 0.076(3) -0.021(3) 0.037(3) 0.023(4)
C14 0.050(2) 0.090(3) 0.0319(17) -0.0007(19) 0.0106(15) 0.000(2)
C15 0.057(2) 0.098(3) 0.040(2) -0.009(2) 0.0120(17) 0.005(3)
C16 0.066(3) 0.120(4) 0.039(2) -0.001(2) 0.0225(19) 0.008(3)
C17 0.061(3) 0.127(5) 0.042(2) 0.012(3) 0.011(2) 0.010(3)
C18 0.052(2) 0.099(3) 0.059(2) 0.011(3) 0.011(2) 0.016(2)
C19 0.045(2) 0.111(4) 0.048(2) -0.003(2) 0.0107(18) 0.009(3)
C20 0.117(5) 0.103(4) 0.069(3) -0.018(3) 0.036(3) 0.021(4)
C21 0.108(5) 0.130(7) 0.069(3) 0.049(4) 0.034(3) 0.022(5)
C22 0.077(3) 0.118(5) 0.075(3) -0.014(4) 0.031(3) 0.024(3)

_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
O1 C3 1.418(5) . ?
O1 C4 1.428(5) . ?
N1 C1 1.322(5) . ?
N1 N2 1.381(5) . ?
N1 C14 1.442(5) . ?
N2 C2 1.313(5) . ?
N3 C1 1.329(5) . ?
N3 C2 1.353(5) . ?
N3 C5 1.473(5) . ?
F1 B1 1.343(7) . ?
F2 B1 1.390(7) . ?
F2 H1 2.8963 . ?
F3 B1 1.410(8) . ?
F4 B1 1.315(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.483(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.518(6) . ?
C4 C5 1.569(6) . ?
C4 H4 0.9800 . ?
C5 C6 1.524(6) . ?
C5 H5 0.9800 . ?
C6 C7 1.523(6) . ?
C6 C10 1.541(7) . ?
C6 H6 0.9800 . ?
C7 C8 1.557(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.534(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.540(7) . ?
C9 C10 1.552(9) . ?
C10 C13 1.540(7) . ?
C10 C12 1.558(8) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.371(7) . ?
C14 C15 1.402(6) . ?
C15 C16 1.393(6) . ?
C15 C20 1.484(8) . ?
C16 C17 1.364(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(7) . ?
C17 C21 1.524(7) . ?
C18 C19 1.396(6) . ?
C18 H18 0.9300 . ?
C19 C22 1.510(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C4 113.7(4) . . ?
C1 N1 N2 111.1(3) . . ?
C1 N1 C14 126.6(4) . . ?
N2 N1 C14 122.3(3) . . ?
C2 N2 N1 103.5(3) . . ?
C1 N3 C2 107.5(3) . . ?
C1 N3 C5 127.3(3) . . ?
C2 N3 C5 124.3(3) . . ?
B1 F2 H1 86.5 . . ?
F4 B1 F1 113.6(5) . . ?
F4 B1 F2 108.9(6) . . ?
F1 B1 F2 107.0(5) . . ?
F4 B1 F3 109.7(5) . . ?
F1 B1 F3 110.3(6) . . ?
F2 B1 F3 107.1(5) . . ?
N1 C1 N3 106.7(3) . . ?
N1 C1 H1 126.7 . . ?
N3 C1 H1 126.7 . . ?
N2 C2 N3 111.2(4) . . ?
N2 C2 C3 129.3(4) . . ?
N3 C2 C3 119.5(4) . . ?
O1 C3 C2 107.5(4) . . ?
O1 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
O1 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
O1 C4 C9 111.0(4) . . ?
O1 C4 C5 113.2(3) . . ?
C9 C4 C5 101.1(4) . . ?
O1 C4 H4 110.4 . . ?
C9 C4 H4 110.4 . . ?
C5 C4 H4 110.4 . . ?
N3 C5 C6 117.7(3) . . ?
N3 C5 C4 110.3(3) . . ?
C6 C5 C4 104.5(3) . . ?
N3 C5 H5 108.0 . . ?
C6 C5 H5 108.0 . . ?
C4 C5 H5 108.0 . . ?
C7 C6 C5 103.1(4) . . ?
C7 C6 C10 103.2(3) . . ?
C5 C6 C10 103.9(4) . . ?
C7 C6 H6 115.0 . . ?
C5 C6 H6 115.0 . . ?
C10 C6 H6 115.0 . . ?
C6 C7 C8 101.7(4) . . ?
C6 C7 H7A 111.4 . . ?
C8 C7 H7A 111.4 . . ?
C6 C7 H7B 111.4 . . ?
C8 C7 H7B 111.4 . . ?
H7A C7 H7B 109.3 . . ?
C9 C8 C7 104.3(4) . . ?
C9 C8 H8A 110.9 . . ?
C7 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C4 C9 C8 104.5(4) . . ?
C4 C9 C11 112.8(5) . . ?
C8 C9 C11 112.5(4) . . ?
C4 C9 C10 103.4(3) . . ?
C8 C9 C10 102.7(5) . . ?
C11 C9 C10 119.4(6) . . ?
C13 C10 C6 114.9(4) . . ?
C13 C10 C9 117.7(5) . . ?
C6 C10 C9 93.3(4) . . ?
C13 C10 C12 105.4(5) . . ?
C6 C10 C12 113.0(5) . . ?
C9 C10 C12 112.6(5) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 124.1(4) . . ?
C19 C14 N1 119.0(4) . . ?
C15 C14 N1 116.9(4) . . ?
C16 C15 C14 114.6(4) . . ?
C16 C15 C20 122.5(4) . . ?
C14 C15 C20 122.9(4) . . ?
C17 C16 C15 123.8(4) . . ?
C17 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
C16 C17 C18 118.7(4) . . ?
C16 C17 C21 121.2(5) . . ?
C18 C17 C21 120.0(6) . . ?
C17 C18 C19 121.4(5) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C14 C19 C18 117.3(4) . . ?
C14 C19 C22 122.9(5) . . ?
C18 C19 C22 119.8(5) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C1 N1 N2 C2 -0.2(5) . . . . ?
C14 N1 N2 C2 178.5(4) . . . . ?
H1 F2 B1 F4 126.0 . . . . ?
H1 F2 B1 F1 2.9 . . . . ?
H1 F2 B1 F3 -115.4 . . . . ?
N2 N1 C1 N3 -0.6(5) . . . . ?
C14 N1 C1 N3 -179.2(4) . . . . ?
C2 N3 C1 N1 1.1(5) . . . . ?
C5 N3 C1 N1 170.8(4) . . . . ?
N1 N2 C2 N3 0.9(5) . . . . ?
N1 N2 C2 C3 -178.7(6) . . . . ?
C1 N3 C2 N2 -1.3(5) . . . . ?
C5 N3 C2 N2 -171.4(4) . . . . ?
C1 N3 C2 C3 178.3(5) . . . . ?
C5 N3 C2 C3 8.2(7) . . . . ?
C4 O1 C3 C2 -63.2(7) . . . . ?
N2 C2 C3 O1 -149.8(5) . . . . ?
N3 C2 C3 O1 30.6(7) . . . . ?
C3 O1 C4 C9 169.2(5) . . . . ?
C3 O1 C4 C5 56.3(6) . . . . ?
C1 N3 C5 C6 56.1(5) . . . . ?
C2 N3 C5 C6 -135.8(4) . . . . ?
C1 N3 C5 C4 175.8(4) . . . . ?
C2 N3 C5 C4 -16.1(6) . . . . ?
O1 C4 C5 N3 -14.8(5) . . . . ?
C9 C4 C5 N3 -133.6(4) . . . . ?
O1 C4 C5 C6 112.6(4) . . . . ?
C9 C4 C5 C6 -6.2(5) . . . . ?
N3 C5 C6 C7 -159.2(3) . . . . ?
C4 C5 C6 C7 78.0(4) . . . . ?
N3 C5 C6 C10 93.4(4) . . . . ?
C4 C5 C6 C10 -29.3(4) . . . . ?
C5 C6 C7 C8 -69.2(4) . . . . ?
C10 C6 C7 C8 38.7(5) . . . . ?
C6 C7 C8 C9 -4.2(5) . . . . ?
O1 C4 C9 C8 172.0(4) . . . . ?
C5 C4 C9 C8 -67.6(5) . . . . ?
O1 C4 C9 C11 49.5(7) . . . . ?
C5 C4 C9 C11 169.9(5) . . . . ?
O1 C4 C9 C10 -80.8(5) . . . . ?
C5 C4 C9 C10 39.5(5) . . . . ?
C7 C8 C9 C4 76.5(6) . . . . ?
C7 C8 C9 C11 -160.8(6) . . . . ?
C7 C8 C9 C10 -31.2(5) . . . . ?
C7 C6 C10 C13 -179.0(5) . . . . ?
C5 C6 C10 C13 -71.7(6) . . . . ?
C7 C6 C10 C9 -56.3(4) . . . . ?
C5 C6 C10 C9 51.0(4) . . . . ?
C7 C6 C10 C12 60.0(7) . . . . ?
C5 C6 C10 C12 167.3(5) . . . . ?
C4 C9 C10 C13 64.5(5) . . . . ?
C8 C9 C10 C13 173.0(4) . . . . ?
C11 C9 C10 C13 -61.9(5) . . . . ?
C4 C9 C10 C6 -56.0(4) . . . . ?
C8 C9 C10 C6 52.5(4) . . . . ?
C11 C9 C10 C6 177.7(4) . . . . ?
C4 C9 C10 C12 -172.7(4) . . . . ?
C8 C9 C10 C12 -64.2(5) . . . . ?
C11 C9 C10 C12 61.0(6) . . . . ?
C1 N1 C14 C19 -93.7(5) . . . . ?
N2 N1 C14 C19 87.8(6) . . . . ?
C1 N1 C14 C15 85.3(6) . . . . ?
N2 N1 C14 C15 -93.2(5) . . . . ?
C19 C14 C15 C16 2.3(7) . . . . ?
N1 C14 C15 C16 -176.6(4) . . . . ?
C19 C14 C15 C20 -179.4(5) . . . . ?
N1 C14 C15 C20 1.7(7) . . . . ?
C14 C15 C16 C17 -0.8(7) . . . . ?
C20 C15 C16 C17 -179.1(5) . . . . ?
C15 C16 C17 C18 -1.1(8) . . . . ?
C15 C16 C17 C21 177.8(5) . . . . ?
C16 C17 C18 C19 1.8(8) . . . . ?
C21 C17 C18 C19 -177.1(5) . . . . ?
C15 C14 C19 C18 -1.7(7) . . . . ?
N1 C14 C19 C18 177.2(4) . . . . ?
C15 C14 C19 C22 178.3(5) . . . . ?
N1 C14 C19 C22 -2.7(7) . . . . ?
C17 C18 C19 C14 -0.5(7) . . . . ?
C17 C18 C19 C22 179.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.054