#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:15:33 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250077 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/44/4134419.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4134419
loop_
_publ_author_name
'Hermann, Alexander'
'Arrowsmith, Merle'
'Trujillo-Gonzalez, Daniel E'
'Jiménez-Halla, J Oscar C'
'Vargas, Alfredo'
'Braunschweig, Holger'
_publ_section_title
;
 Trapping of a Borirane Intermediate in the Reductive Coupling of an
 Arylborane to a Diborene.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5562
_journal_page_last               5567
_journal_paper_doi               10.1021/jacs.0c02306
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C37 H50 B F6 N3'
_chemical_formula_sum            'C37 H50 B F6 N3'
_chemical_formula_weight         661.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                85.773(16)
_cell_angle_beta                 69.850(10)
_cell_angle_gamma                81.738(13)
_cell_formula_units_Z            2
_cell_length_a                   11.5551(19)
_cell_length_b                   12.353(3)
_cell_length_c                   13.320(3)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.68
_cell_measurement_theta_min      2.36
_cell_volume                     1765.8(7)
_computing_cell_refinement       'Saint+ ver. V8.37A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.37A (Bruker AXS)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CMOS area detector (Photon II)'
_diffrn_detector_area_resol_mean 7.5
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            41312
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.037
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0406P)²+0.4859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5428
_reflns_number_total             6963
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c02306_si_002.cif
_cod_data_source_block           test_a
_cod_depositor_comments
'Adding full bibliography for 4134419--4134425.cif.'
_cod_database_code               4134419
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
B1 B 0.32636(14) 0.24337(13) 0.76869(13) 0.0166(3) Uani 1 1 d . . . . .
N1 N 0.15766(10) 0.14617(9) 0.72988(9) 0.0171(3) Uani 1 1 d . . . . .
F1 F 0.43940(9) 0.57785(8) 0.93880(8) 0.0364(2) Uani 1 1 d . . . . .
C1 C 0.30134(12) 0.37457(11) 0.76660(11) 0.0165(3) Uani 1 1 d . . . . .
N2 N 0.44302(10) 0.20334(9) 0.90947(9) 0.0177(3) Uani 1 1 d . . . . .
F2 F 0.57894(8) 0.55342(8) 0.78455(9) 0.0401(3) Uani 1 1 d . . . . .
C2 C 0.37679(13) 0.43378(12) 0.80152(12) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.434985 0.392978 0.830148 0.024 Uiso 1 1 calc R U . . .
C3 C 0.37139(13) 0.54640(12) 0.79675(11) 0.0196(3) Uani 1 1 d . . . . .
N3 N 0.56668(10) 0.21870(10) 0.74706(9) 0.0187(3) Uani 1 1 d . . . . .
F3 F 0.45574(9) 0.70405(7) 0.81747(8) 0.0367(2) Uani 1 1 d . . . . .
C4 C 0.28665(13) 0.61191(12) 0.75878(11) 0.0197(3) Uani 1 1 d . . . . .
H4 H 0.282106 0.689429 0.755392 0.024 Uiso 1 1 calc R U . . .
F4 F 0.12417(10) 0.73134(7) 0.67715(9) 0.0415(3) Uani 1 1 d . . . . .
C5 C 0.20885(12) 0.55814(11) 0.72601(11) 0.0175(3) Uani 1 1 d . . . . .
F5 F 0.11169(8) 0.59341(8) 0.59516(7) 0.0309(2) Uani 1 1 d . . . . .
C6 C 0.21648(12) 0.44449(11) 0.72809(11) 0.0166(3) Uani 1 1 d . . . . .
H6 H 0.162335 0.412384 0.702543 0.020 Uiso 1 1 calc R U . . .
F6 F -0.00407(8) 0.61771(8) 0.75796(7) 0.0343(2) Uani 1 1 d . . . . .
C7 C 0.46013(14) 0.59501(12) 0.83353(13) 0.0253(3) Uani 1 1 d . . . . .
C8 C 0.11124(13) 0.62430(12) 0.68950(12) 0.0217(3) Uani 1 1 d . . . . .
C9 C 0.27006(12) 0.15006(11) 0.74940(11) 0.0159(3) Uani 1 1 d . . . . .
C10 C 0.12179(13) 0.03511(12) 0.73148(13) 0.0223(3) Uani 1 1 d . . . . .
C11 C 0.24910(13) -0.03241(12) 0.70427(13) 0.0226(3) Uani 1 1 d . . . . .
H11A H 0.287936 -0.039668 0.625834 0.027 Uiso 1 1 calc R U . . .
H11B H 0.241388 -0.106539 0.737619 0.027 Uiso 1 1 calc R U . . .
C12 C 0.32871(13) 0.02787(11) 0.74794(12) 0.0198(3) Uani 1 1 d . . . . .
C13 C 0.06029(16) 0.02299(13) 0.64890(15) 0.0340(4) Uani 1 1 d . . . . .
H13A H 0.042290 -0.052489 0.651261 0.051 Uiso 1 1 calc R U . . .
H13B H 0.116420 0.040626 0.577359 0.051 Uiso 1 1 calc R U . . .
H13C H -0.017335 0.073051 0.665067 0.051 Uiso 1 1 calc R U . . .
C14 C 0.03278(15) 0.00131(13) 0.84099(14) 0.0324(4) Uani 1 1 d . . . . .
H14A H 0.024080 -0.076471 0.841201 0.049 Uiso 1 1 calc R U . . .
H14B H -0.048712 0.044909 0.854734 0.049 Uiso 1 1 calc R U . . .
H14C H 0.066204 0.013921 0.896893 0.049 Uiso 1 1 calc R U . . .
C16 C 0.46347(14) 0.00515(13) 0.67218(15) 0.0324(4) Uani 1 1 d . . . . .
H16A H 0.486444 -0.073885 0.662628 0.049 Uiso 1 1 calc R U . . .
H16B H 0.518845 0.033190 0.702820 0.049 Uiso 1 1 calc R U . . .
H16C H 0.471167 0.041638 0.602724 0.049 Uiso 1 1 calc R U . . .
C15 C 0.32556(16) -0.01764(12) 0.85924(14) 0.0289(4) Uani 1 1 d . . . . .
H15A H 0.345914 -0.097429 0.857021 0.043 Uiso 1 1 calc R U . . .
H15B H 0.242305 0.001473 0.911200 0.043 Uiso 1 1 calc R U . . .
H15C H 0.386459 0.013993 0.880476 0.043 Uiso 1 1 calc R U . . .
C17 C 0.07881(12) 0.23944(11) 0.71088(11) 0.0166(3) Uani 1 1 d . . . . .
C18 C 0.09835(13) 0.27685(12) 0.60439(12) 0.0212(3) Uani 1 1 d . . . . .
C19 C 0.01544(14) 0.36253(12) 0.58564(13) 0.0252(3) Uani 1 1 d . . . . .
H19 H 0.026819 0.388285 0.514311 0.030 Uiso 1 1 calc R U . . .
C20 C -0.08315(14) 0.41100(12) 0.66857(13) 0.0266(4) Uani 1 1 d . . . . .
H20 H -0.140285 0.467759 0.653773 0.032 Uiso 1 1 calc R U . . .
C21 C -0.09848(13) 0.37693(12) 0.77270(13) 0.0234(3) Uani 1 1 d . . . . .
H21 H -0.165279 0.411944 0.829305 0.028 Uiso 1 1 calc R U . . .
C22 C -0.01751(12) 0.29173(11) 0.79668(12) 0.0187(3) Uani 1 1 d . . . . .
C23 C -0.03191(13) 0.26434(12) 0.91302(12) 0.0216(3) Uani 1 1 d . . . . .
H23 H 0.030683 0.200165 0.915442 0.026 Uiso 1 1 calc R U . . .
C24 C -0.16160(14) 0.23388(13) 0.97767(13) 0.0279(4) Uani 1 1 d . . . . .
H24A H -0.165113 0.212254 1.050842 0.042 Uiso 1 1 calc R U . . .
H24B H -0.178475 0.172809 0.944017 0.042 Uiso 1 1 calc R U . . .
H24C H -0.224040 0.297117 0.979442 0.042 Uiso 1 1 calc R U . . .
C25 C -0.00736(15) 0.36041(14) 0.96649(13) 0.0294(4) Uani 1 1 d . . . . .
H25A H -0.014013 0.339564 1.040511 0.044 Uiso 1 1 calc R U . . .
H25B H -0.068730 0.423880 0.965973 0.044 Uiso 1 1 calc R U . . .
H25C H 0.076320 0.379107 0.927116 0.044 Uiso 1 1 calc R U . . .
C26 C 0.21148(15) 0.23257(13) 0.51116(12) 0.0281(4) Uani 1 1 d . . . . .
H26 H 0.248215 0.161767 0.535815 0.034 Uiso 1 1 calc R U . . .
C27 C 0.31067(16) 0.31106(15) 0.47987(13) 0.0362(4) Uani 1 1 d . . . . .
H27A H 0.382749 0.280967 0.420322 0.054 Uiso 1 1 calc R U . . .
H27B H 0.336417 0.319960 0.541296 0.054 Uiso 1 1 calc R U . . .
H27C H 0.276135 0.382339 0.458030 0.054 Uiso 1 1 calc R U . . .
C28 C 0.17896(19) 0.20930(17) 0.41298(14) 0.0436(5) Uani 1 1 d . . . . .
H28A H 0.252135 0.170819 0.360102 0.065 Uiso 1 1 calc R U . . .
H28B H 0.152781 0.278531 0.381379 0.065 Uiso 1 1 calc R U . . .
H28C H 0.111224 0.163686 0.434802 0.065 Uiso 1 1 calc R U . . .
C29 C 0.44572(12) 0.21313(11) 0.80619(11) 0.0166(3) Uani 1 1 d . . . . .
C30 C 0.56030(13) 0.20543(12) 0.91375(12) 0.0221(3) Uani 1 1 d . . . . .
H30 H 0.582376 0.201169 0.976475 0.027 Uiso 1 1 calc R U . . .
C31 C 0.63743(13) 0.21463(12) 0.81238(12) 0.0225(3) Uani 1 1 d . . . . .
H31 H 0.724368 0.217744 0.789991 0.027 Uiso 1 1 calc R U . . .
C32 C 0.32807(13) 0.20200(13) 1.00459(12) 0.0233(3) Uani 1 1 d . . . . .
H32 H 0.260918 0.182721 0.980359 0.028 Uiso 1 1 calc R U . . .
C33 C 0.28636(15) 0.31452(14) 1.05341(13) 0.0313(4) Uani 1 1 d . . . . .
H33A H 0.211485 0.311716 1.116578 0.047 Uiso 1 1 calc R U . . .
H33B H 0.268057 0.367520 1.000739 0.047 Uiso 1 1 calc R U . . .
H33C H 0.352651 0.336835 1.074393 0.047 Uiso 1 1 calc R U . . .
C34 C 0.34803(16) 0.11498(15) 1.08609(13) 0.0356(4) Uani 1 1 d . . . . .
H34A H 0.268664 0.107978 1.143264 0.053 Uiso 1 1 calc R U . . .
H34B H 0.407204 0.136208 1.116625 0.053 Uiso 1 1 calc R U . . .
H34C H 0.381087 0.044729 1.050874 0.053 Uiso 1 1 calc R U . . .
C35 C 0.61419(13) 0.23213(12) 0.62882(12) 0.0232(3) Uani 1 1 d . . . . .
H35 H 0.552185 0.208522 0.600682 0.028 Uiso 1 1 calc R U . . .
C36 C 0.73635(15) 0.15839(15) 0.58204(14) 0.0347(4) Uani 1 1 d . . . . .
H36A H 0.759291 0.158061 0.504040 0.052 Uiso 1 1 calc R U . . .
H36B H 0.726769 0.083775 0.611321 0.052 Uiso 1 1 calc R U . . .
H36C H 0.801617 0.185865 0.600673 0.052 Uiso 1 1 calc R U . . .
C37 C 0.62832(15) 0.35100(14) 0.59404(13) 0.0319(4) Uani 1 1 d . . . . .
H37A H 0.659170 0.357046 0.515742 0.048 Uiso 1 1 calc R U . . .
H37B H 0.687394 0.376648 0.622039 0.048 Uiso 1 1 calc R U . . .
H37C H 0.547486 0.395899 0.621939 0.048 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 1.00 0.0580
-1.00 1.00 -1.00 0.0600
1.00 -1.00 2.00 0.0590
-1.00 1.00 -2.00 0.0450
-2.00 1.00 -1.00 0.0600
0.00 0.00 -1.00 0.0410
1.00 0.00 2.00 0.0480
-1.00 0.00 -2.00 0.0290
2.00 0.00 1.00 0.0630
-2.00 0.00 -1.00 0.0410
-2.00 1.00 2.00 0.0570
2.00 -1.00 -2.00 0.0590
1.00 1.00 2.00 0.0580
-1.00 -1.00 -2.00 0.0370
1.00 2.00 1.00 0.0750
-1.00 -2.00 -1.00 0.0360
2.00 0.00 -1.00 0.0560
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
C9 B1 C1 138.26(13) . . ?
C9 B1 C29 116.36(12) . . ?
C1 B1 C29 105.35(11) . . ?
C9 N1 C17 124.95(11) . . ?
C9 N1 C10 115.65(11) . . ?
C17 N1 C10 119.39(11) . . ?
C6 C1 C2 112.32(12) . . ?
C6 C1 B1 128.99(13) . . ?
C2 C1 B1 118.59(12) . . ?
C29 N2 C30 110.33(12) . . ?
C29 N2 C32 124.70(12) . . ?
C30 N2 C32 124.70(12) . . ?
C3 C2 C1 124.62(13) . . ?
C3 C2 H2 117.7 . . ?
C1 C2 H2 117.7 . . ?
C2 C3 C4 121.22(13) . . ?
C2 C3 C7 117.64(13) . . ?
C4 C3 C7 121.15(13) . . ?
C29 N3 C31 110.55(12) . . ?
C29 N3 C35 124.27(12) . . ?
C31 N3 C35 125.14(12) . . ?
C3 C4 C5 116.39(13) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
C4 C5 C6 122.43(13) . . ?
C4 C5 C8 118.96(13) . . ?
C6 C5 C8 118.60(13) . . ?
C5 C6 C1 122.98(13) . . ?
C5 C6 H6 118.5 . . ?
C1 C6 H6 118.5 . . ?
F2 C7 F3 106.04(12) . . ?
F2 C7 F1 105.58(12) . . ?
F3 C7 F1 105.48(12) . . ?
F2 C7 C3 112.82(12) . . ?
F3 C7 C3 113.58(12) . . ?
F1 C7 C3 112.65(13) . . ?
F5 C8 F6 105.80(12) . . ?
F5 C8 F4 105.72(12) . . ?
F6 C8 F4 106.09(12) . . ?
F5 C8 C5 113.01(12) . . ?
F6 C8 C5 112.82(12) . . ?
F4 C8 C5 112.77(12) . . ?
N1 C9 B1 131.22(12) . . ?
N1 C9 C12 104.34(11) . . ?
B1 C9 C12 124.43(12) . . ?
N1 C10 C11 99.78(11) . . ?
N1 C10 C13 113.06(13) . . ?
C11 C10 C13 111.87(13) . . ?
N1 C10 C14 113.06(12) . . ?
C11 C10 C14 111.84(13) . . ?
C13 C10 C14 107.26(13) . . ?
C10 C11 C12 107.21(11) . . ?
C10 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
C10 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
C16 C12 C15 107.27(13) . . ?
C16 C12 C11 107.01(12) . . ?
C15 C12 C11 111.12(12) . . ?
C16 C12 C9 114.66(12) . . ?
C15 C12 C9 112.81(12) . . ?
C11 C12 C9 103.84(11) . . ?
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 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 C17 C18 120.95(13) . . ?
C22 C17 N1 120.58(12) . . ?
C18 C17 N1 118.46(12) . . ?
C19 C18 C17 118.21(13) . . ?
C19 C18 C26 119.24(14) . . ?
C17 C18 C26 122.39(13) . . ?
C20 C19 C18 121.41(14) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C21 C20 C19 119.94(14) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 121.25(14) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C17 118.07(13) . . ?
C21 C22 C23 118.94(13) . . ?
C17 C22 C23 122.88(12) . . ?
C22 C23 C24 112.17(12) . . ?
C22 C23 C25 111.16(12) . . ?
C24 C23 C25 108.75(12) . . ?
C22 C23 H23 108.2 . . ?
C24 C23 H23 108.2 . . ?
C25 C23 H23 108.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C26 C27 110.69(13) . . ?
C18 C26 C28 113.03(14) . . ?
C27 C26 C28 110.11(14) . . ?
C18 C26 H26 107.6 . . ?
C27 C26 H26 107.6 . . ?
C28 C26 H26 107.6 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 N2 104.91(12) . . ?
N3 C29 B1 127.79(12) . . ?
N2 C29 B1 125.50(12) . . ?
C31 C30 N2 107.07(13) . . ?
C31 C30 H30 126.5 . . ?
N2 C30 H30 126.5 . . ?
C30 C31 N3 107.13(12) . . ?
C30 C31 H31 126.4 . . ?
N3 C31 H31 126.4 . . ?
N2 C32 C33 110.66(12) . . ?
N2 C32 C34 110.51(12) . . ?
C33 C32 C34 111.49(14) . . ?
N2 C32 H32 108.0 . . ?
C33 C32 H32 108.0 . . ?
C34 C32 H32 108.0 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N3 C35 C37 111.58(12) . . ?
N3 C35 C36 110.23(12) . . ?
C37 C35 C36 111.23(13) . . ?
N3 C35 H35 107.9 . . ?
C37 C35 H35 107.9 . . ?
C36 C35 H35 107.9 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
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 C9 1.481(2) . ?
B1 C1 1.605(2) . ?
B1 C29 1.609(2) . ?
N1 C9 1.4175(18) . ?
N1 C17 1.4270(17) . ?
N1 C10 1.4858(18) . ?
F1 C7 1.3445(19) . ?
C1 C6 1.4172(19) . ?
C1 C2 1.423(2) . ?
N2 C29 1.3620(18) . ?
N2 C30 1.3798(18) . ?
N2 C32 1.4878(18) . ?
F2 C7 1.3431(17) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C3 C7 1.490(2) . ?
N3 C29 1.3564(17) . ?
N3 C31 1.3784(19) . ?
N3 C35 1.4837(19) . ?
F3 C7 1.3445(17) . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
F4 C8 1.3437(17) . ?
C5 C6 1.393(2) . ?
C5 C8 1.494(2) . ?
F5 C8 1.3380(18) . ?
C6 H6 0.9500 . ?
F6 C8 1.3404(17) . ?
C9 C12 1.5618(19) . ?
C10 C11 1.5217(19) . ?
C10 C13 1.527(2) . ?
C10 C14 1.536(2) . ?
C11 C12 1.539(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.535(2) . ?
C12 C15 1.537(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 C22 1.410(2) . ?
C17 C18 1.410(2) . ?
C18 C19 1.391(2) . ?
C18 C26 1.525(2) . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.378(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.399(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.518(2) . ?
C23 C24 1.534(2) . ?
C23 C25 1.535(2) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.536(2) . ?
C26 C28 1.536(2) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C30 C31 1.345(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.520(2) . ?
C32 C34 1.522(2) . ?
C32 H32 1.0000 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C37 1.521(2) . ?
C35 C36 1.523(2) . ?
C35 H35 1.0000 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 B1 C1 C6 -9.8(3) . . . . ?
C29 B1 C1 C6 172.24(13) . . . . ?
C9 B1 C1 C2 174.24(16) . . . . ?
C29 B1 C1 C2 -3.69(16) . . . . ?
C6 C1 C2 C3 -1.4(2) . . . . ?
B1 C1 C2 C3 175.13(13) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C1 C2 C3 C7 -178.03(13) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C7 C3 C4 C5 179.63(13) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C3 C4 C5 C8 176.94(13) . . . . ?
C4 C5 C6 C1 1.9(2) . . . . ?
C8 C5 C6 C1 -176.62(12) . . . . ?
C2 C1 C6 C5 -0.37(19) . . . . ?
B1 C1 C6 C5 -176.50(13) . . . . ?
C2 C3 C7 F2 53.82(19) . . . . ?
C4 C3 C7 F2 -125.99(15) . . . . ?
C2 C3 C7 F3 174.54(13) . . . . ?
C4 C3 C7 F3 -5.3(2) . . . . ?
C2 C3 C7 F1 -65.61(17) . . . . ?
C4 C3 C7 F1 114.58(15) . . . . ?
C4 C5 C8 F5 129.80(14) . . . . ?
C6 C5 C8 F5 -51.61(17) . . . . ?
C4 C5 C8 F6 -110.21(15) . . . . ?
C6 C5 C8 F6 68.37(17) . . . . ?
C4 C5 C8 F4 9.96(19) . . . . ?
C6 C5 C8 F4 -171.45(12) . . . . ?
C17 N1 C9 B1 8.6(2) . . . . ?
C10 N1 C9 B1 -170.49(14) . . . . ?
C17 N1 C9 C12 -171.91(12) . . . . ?
C10 N1 C9 C12 8.95(15) . . . . ?
C1 B1 C9 N1 -7.1(3) . . . . ?
C29 B1 C9 N1 170.67(13) . . . . ?
C1 B1 C9 C12 173.56(15) . . . . ?
C29 B1 C9 C12 -8.7(2) . . . . ?
C9 N1 C10 C11 -24.64(15) . . . . ?
C17 N1 C10 C11 156.17(12) . . . . ?
C9 N1 C10 C13 -143.60(13) . . . . ?
C17 N1 C10 C13 37.21(18) . . . . ?
C9 N1 C10 C14 94.28(15) . . . . ?
C17 N1 C10 C14 -84.91(16) . . . . ?
N1 C10 C11 C12 29.95(15) . . . . ?
C13 C10 C11 C12 149.78(13) . . . . ?
C14 C10 C11 C12 -89.87(15) . . . . ?
C10 C11 C12 C16 -147.85(13) . . . . ?
C10 C11 C12 C15 95.34(14) . . . . ?
C10 C11 C12 C9 -26.21(15) . . . . ?
N1 C9 C12 C16 127.24(13) . . . . ?
B1 C9 C12 C16 -53.27(19) . . . . ?
N1 C9 C12 C15 -109.56(13) . . . . ?
B1 C9 C12 C15 69.93(17) . . . . ?
N1 C9 C12 C11 10.84(14) . . . . ?
B1 C9 C12 C11 -169.67(13) . . . . ?
C9 N1 C17 C22 -89.75(17) . . . . ?
C10 N1 C17 C22 89.36(16) . . . . ?
C9 N1 C17 C18 91.20(16) . . . . ?
C10 N1 C17 C18 -89.69(16) . . . . ?
C22 C17 C18 C19 -3.8(2) . . . . ?
N1 C17 C18 C19 175.20(13) . . . . ?
C22 C17 C18 C26 171.59(13) . . . . ?
N1 C17 C18 C26 -9.4(2) . . . . ?
C17 C18 C19 C20 0.6(2) . . . . ?
C26 C18 C19 C20 -175.01(14) . . . . ?
C18 C19 C20 C21 2.1(2) . . . . ?
C19 C20 C21 C22 -1.6(2) . . . . ?
C20 C21 C22 C17 -1.6(2) . . . . ?
C20 C21 C22 C23 174.64(13) . . . . ?
C18 C17 C22 C21 4.4(2) . . . . ?
N1 C17 C22 C21 -174.67(12) . . . . ?
C18 C17 C22 C23 -171.75(13) . . . . ?
N1 C17 C22 C23 9.2(2) . . . . ?
C21 C22 C23 C24 58.47(17) . . . . ?
C17 C22 C23 C24 -125.46(15) . . . . ?
C21 C22 C23 C25 -63.53(17) . . . . ?
C17 C22 C23 C25 112.54(15) . . . . ?
C19 C18 C26 C27 75.71(18) . . . . ?
C17 C18 C26 C27 -99.68(17) . . . . ?
C19 C18 C26 C28 -48.3(2) . . . . ?
C17 C18 C26 C28 136.27(16) . . . . ?
C31 N3 C29 N2 -1.17(15) . . . . ?
C35 N3 C29 N2 -178.73(12) . . . . ?
C31 N3 C29 B1 164.03(13) . . . . ?
C35 N3 C29 B1 -13.5(2) . . . . ?
C30 N2 C29 N3 1.37(15) . . . . ?
C32 N2 C29 N3 175.63(12) . . . . ?
C30 N2 C29 B1 -164.27(13) . . . . ?
C32 N2 C29 B1 10.0(2) . . . . ?
C9 B1 C29 N3 104.63(16) . . . . ?
C1 B1 C29 N3 -76.90(16) . . . . ?
C9 B1 C29 N2 -93.02(17) . . . . ?
C1 B1 C29 N2 85.45(16) . . . . ?
C29 N2 C30 C31 -1.08(16) . . . . ?
C32 N2 C30 C31 -175.33(13) . . . . ?
N2 C30 C31 N3 0.33(16) . . . . ?
C29 N3 C31 C30 0.54(16) . . . . ?
C35 N3 C31 C30 178.07(13) . . . . ?
C29 N2 C32 C33 -98.21(16) . . . . ?
C30 N2 C32 C33 75.23(17) . . . . ?
C29 N2 C32 C34 137.80(14) . . . . ?
C30 N2 C32 C34 -48.76(19) . . . . ?
C29 N3 C35 C37 97.54(16) . . . . ?
C31 N3 C35 C37 -79.66(17) . . . . ?
C29 N3 C35 C36 -138.34(14) . . . . ?
C31 N3 C35 C36 44.45(19) . . . . ?
