#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:15:33 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250077 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/44/4134422.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_4134422
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         'C34 H38 B2 F12 N4'
_chemical_formula_sum            'C34 H38 B2 F12 N4'
_chemical_formula_weight         752.30
_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-2018/3
_cell_angle_alpha                114.541(18)
_cell_angle_beta                 102.10(3)
_cell_angle_gamma                97.48(3)
_cell_formula_units_Z            1
_cell_length_a                   8.849(3)
_cell_length_b                   10.927(4)
_cell_length_c                   10.940(4)
_cell_measurement_reflns_used    5157
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.70
_cell_measurement_theta_min      2.73
_cell_volume                     912.4(6)
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.1089
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20370
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.996
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.113
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     329
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_gt           0.0795
_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)+(0.0718P)²+2.3704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.2092
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2276
_reflns_number_total             3569
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c02306_si_008.cif
_cod_data_source_block           final_a
_cod_depositor_comments
'Adding full bibliography for 4134419--4134425.cif.'
_cod_database_code               4134422
_shelx_shelxl_version_number     2018/3
_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   0.971
_shelx_estimated_absorpt_t_max   0.986
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
C1_1 C 0.4080(4) 0.4708(3) 0.6630(3) 0.0193(9) Uani 0.889(5) 1 d DG . P A 1
C2_1 C 0.3744(4) 0.5965(2) 0.7397(3) 0.0201(9) Uani 0.889(5) 1 d DG . P A 1
H2_1 H 0.396354 0.671088 0.717682 0.024 Uiso 0.889(5) 1 calc R U P A 1
C3_1 C 0.3086(4) 0.6129(2) 0.8487(3) 0.0207(9) Uani 0.889(5) 1 d DG . P A 1
C4_1 C 0.2764(5) 0.5037(3) 0.8809(4) 0.0222(9) Uani 0.889(5) 1 d DG . P A 1
H4_1 H 0.231502 0.514984 0.955370 0.027 Uiso 0.889(5) 1 calc R U P A 1
C5_1 C 0.3100(5) 0.3781(3) 0.8042(4) 0.0235(9) Uani 0.889(5) 1 d DG . P A 1
C6_1 C 0.3758(4) 0.3616(2) 0.6952(3) 0.0219(9) Uani 0.889(5) 1 d DG . P A 1
H6_1 H 0.398776 0.275698 0.642747 0.026 Uiso 0.889(5) 1 calc R U P A 1
C7_1 C 0.2659(5) 0.7447(4) 0.9226(4) 0.0276(10) Uani 0.889(5) 1 d D U P A 1
F1_1 F 0.3748(4) 0.8558(3) 0.9522(3) 0.0467(9) Uani 0.889(5) 1 d D U P A 1
F2_1 F 0.1284(5) 0.7504(4) 0.8450(4) 0.0636(12) Uani 0.889(5) 1 d D U P A 1
F3_1 F 0.2383(5) 0.7615(3) 1.0448(3) 0.0470(10) Uani 0.889(5) 1 d D U P A 1
C8_1 C 0.2685(6) 0.2574(5) 0.8307(5) 0.0339(11) Uani 0.889(5) 1 d D U P A 1
F4_1 F 0.1937(6) 0.2774(4) 0.9258(4) 0.0737(12) Uani 0.889(5) 1 d D U P A 1
F5_1 F 0.1699(4) 0.1462(3) 0.7105(4) 0.0524(10) Uani 0.889(5) 1 d D U P A 1
F6_1 F 0.3924(4) 0.2082(3) 0.8606(4) 0.0534(9) Uani 0.889(5) 1 d D U P A 1
B1_1 B 0.4823(5) 0.4488(4) 0.5327(4) 0.0167(9) Uani 0.889(5) 1 d D . P A 1
C9_1 C 0.5171(5) 0.2988(4) 0.4649(4) 0.0186(10) Uani 0.889(5) 1 d D . P A 1
N1_1 N 0.6589(7) 0.2658(5) 0.4897(12) 0.0202(11) Uani 0.889(5) 1 d D . P A 1
C10_1 C 0.6417(6) 0.1266(5) 0.4059(5) 0.0291(12) Uani 0.889(5) 1 d D . P A 1
H10_1 H 0.723497 0.078086 0.403084 0.035 Uiso 0.889(5) 1 calc R U P A 1
C11_1 C 0.4889(6) 0.0725(4) 0.3295(5) 0.0271(11) Uani 0.889(5) 1 d D . P A 1
H11_1 H 0.441714 -0.021388 0.261899 0.032 Uiso 0.889(5) 1 calc R U P A 1
N2_1 N 0.4129(7) 0.1791(5) 0.3677(13) 0.0211(12) Uani 0.889(5) 1 d D . P A 1
C1_2 C 0.609(5) 0.483(3) 0.326(4) 0.045(5) Uani 0.111(5) 1 d DG U P A 2
C2_2 C 0.613(5) 0.599(3) 0.303(4) 0.044(5) Uani 0.111(5) 1 d DG U P A 2
H2_2 H 0.571644 0.672577 0.357316 0.053 Uiso 0.111(5) 1 calc R U P A 2
C3_2 C 0.677(6) 0.608(3) 0.201(4) 0.046(5) Uani 0.111(5) 1 d DG U P A 2
C4_2 C 0.738(6) 0.501(4) 0.121(4) 0.048(5) Uani 0.111(5) 1 d DG U P A 2
H4_2 H 0.782133 0.506518 0.051176 0.057 Uiso 0.111(5) 1 calc R U P A 2
C5_2 C 0.734(5) 0.384(3) 0.144(4) 0.051(5) Uani 0.111(5) 1 d DG U P A 2
C6_2 C 0.670(5) 0.376(3) 0.247(4) 0.049(5) Uani 0.111(5) 1 d DG U P A 2
H6_2 H 0.667234 0.296256 0.262234 0.059 Uiso 0.111(5) 1 calc R U P A 2
C7_2 C 0.688(3) 0.724(3) 0.163(3) 0.047(4) Uani 0.111(5) 1 d D U P A 2
F1_2 F 0.696(3) 0.689(2) 0.031(2) 0.043(5) Uani 0.111(5) 1 d D U P A 2
F2_2 F 0.838(3) 0.807(3) 0.232(3) 0.042(5) Uani 0.111(5) 1 d D U P A 2
F3_2 F 0.566(3) 0.780(3) 0.196(3) 0.053(5) Uani 0.111(5) 1 d D U P A 2
C8_2 C 0.801(3) 0.274(3) 0.060(3) 0.058(5) Uani 0.111(5) 1 d D U P A 2
F4_2 F 0.705(4) 0.205(4) -0.067(3) 0.064(6) Uani 0.111(5) 1 d D U P A 2
F5_2 F 0.815(4) 0.188(3) 0.121(3) 0.066(6) Uani 0.111(5) 1 d D U P A 2
F6_2 F 0.941(3) 0.313(3) 0.051(3) 0.075(6) Uani 0.111(5) 1 d D U P A 2
B1_2 B 0.531(5) 0.457(3) 0.441(4) 0.042(5) Uani 0.111(5) 1 d D U P A 2
C9_2 C 0.527(5) 0.306(4) 0.432(5) 0.039(5) Uani 0.111(5) 1 d D U P A 2
N1_2 N 0.646(8) 0.263(4) 0.492(13) 0.040(6) Uani 0.111(5) 1 d D U P A 2
C10_2 C 0.606(5) 0.121(4) 0.443(5) 0.039(6) Uani 0.111(5) 1 d D U P A 2
H10_2 H 0.674650 0.065119 0.458389 0.047 Uiso 0.111(5) 1 calc R U P A 2
C11_2 C 0.452(5) 0.077(3) 0.371(5) 0.040(6) Uani 0.111(5) 1 d D U P A 2
H11_2 H 0.385684 -0.012973 0.333953 0.047 Uiso 0.111(5) 1 calc R U P A 2
N2_2 N 0.408(7) 0.190(5) 0.359(15) 0.039(6) Uani 0.111(5) 1 d D U P A 2
C12 C 0.8068(5) 0.3662(4) 0.5908(4) 0.0302(9) Uani 1 1 d . U . . .
H12 H 0.795851 0.460321 0.603274 0.036 Uiso 1 1 calc R U . A 1
C13 C 0.8279(6) 0.3673(6) 0.7314(5) 0.0560(13) Uani 1 1 d . U . . .
H13A H 0.923202 0.438828 0.799790 0.084 Uiso 1 1 calc R U . . .
H13B H 0.839860 0.276373 0.722803 0.084 Uiso 1 1 calc R U . . .
H13C H 0.734223 0.387280 0.763229 0.084 Uiso 1 1 calc R U . . .
C14 C 0.9475(5) 0.3392(5) 0.5360(5) 0.0412(11) Uani 1 1 d . U . . .
H14A H 1.042188 0.413837 0.600274 0.062 Uiso 1 1 calc R U . . .
H14B H 0.925945 0.335664 0.442813 0.062 Uiso 1 1 calc R U . . .
H14C H 0.966196 0.250374 0.529041 0.062 Uiso 1 1 calc R U . . .
C15 C 0.2440(4) 0.1710(4) 0.3002(4) 0.0298(9) Uani 1 1 d . . . . .
H15 H 0.217841 0.259515 0.357855 0.036 Uiso 1 1 calc R U . A 1
C16 C 0.2268(5) 0.1586(5) 0.1550(5) 0.0412(11) Uani 1 1 d . . . . .
H16A H 0.116373 0.155118 0.111842 0.062 Uiso 1 1 calc R U . . .
H16B H 0.254515 0.073579 0.097062 0.062 Uiso 1 1 calc R U . . .
H16C H 0.298235 0.239090 0.161730 0.062 Uiso 1 1 calc R U . . .
C17 C 0.1338(5) 0.0537(4) 0.3005(5) 0.0447(12) Uani 1 1 d . . . . .
H17A H 0.022978 0.055546 0.266257 0.067 Uiso 1 1 calc R U . . .
H17B H 0.154933 0.064165 0.396352 0.067 Uiso 1 1 calc R U . . .
H17C H 0.151956 -0.034958 0.239028 0.067 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'
F F 0.0171 0.0103 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -2.00 -2.00 0.0990
0.00 1.00 2.00 0.0570
0.00 -1.00 -2.00 0.0740
-1.00 -2.00 -2.00 0.0960
1.00 2.00 2.00 0.0640
1.00 -1.00 0.00 0.1140
1.00 0.00 0.00 0.0980
-1.00 2.00 0.00 0.0830
-2.00 1.00 0.00 0.1090
1.00 -2.00 0.00 0.1340
2.00 1.00 0.00 0.0930
-2.00 -2.00 1.00 0.1230
2.00 2.00 -1.00 0.1080
-1.00 -2.00 1.00 0.1190
1.00 2.00 -1.00 0.1160
-2.00 0.00 1.00 0.1130
1.00 1.00 -1.00 0.1190
0.00 -2.00 1.00 0.1280
-2.00 -1.00 2.00 0.1090
-1.00 -1.00 2.00 0.0890
1.00 1.00 -2.00 0.1130
-1.00 0.00 2.00 0.0770
1.00 0.00 -2.00 0.1090
0.00 -1.00 2.00 0.0580
0.00 1.00 -2.00 0.0840
-1.00 1.00 2.00 0.0590
1.00 -1.00 -2.00 0.0960
0.00 0.00 -1.00 0.0550
1.00 -1.00 2.00 0.0540
0.00 0.00 1.00 0.0320
1.00 0.00 2.00 0.0330
-1.00 0.00 -2.00 0.0790
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
C2_1 C1_1 C6_1 120.0 . . ?
C2_1 C1_1 B1_1 120.6(2) . . ?
C6_1 C1_1 B1_1 119.4(2) . . ?
C3_1 C2_1 C1_1 120.0 . . ?
C3_1 C2_1 H2_1 120.0 . . ?
C1_1 C2_1 H2_1 120.0 . . ?
C2_1 C3_1 C4_1 120.0 . . ?
C2_1 C3_1 C7_1 118.6(2) . . ?
C4_1 C3_1 C7_1 121.3(2) . . ?
C5_1 C4_1 C3_1 120.0 . . ?
C5_1 C4_1 H4_1 120.0 . . ?
C3_1 C4_1 H4_1 120.0 . . ?
C6_1 C5_1 C4_1 120.0 . . ?
C6_1 C5_1 C8_1 118.7(3) . . ?
C4_1 C5_1 C8_1 121.2(3) . . ?
C5_1 C6_1 C1_1 120.0 . . ?
C5_1 C6_1 H6_1 120.0 . . ?
C1_1 C6_1 H6_1 120.0 . . ?
F1_1 C7_1 F3_1 106.8(4) . . ?
F1_1 C7_1 F2_1 106.7(4) . . ?
F3_1 C7_1 F2_1 104.8(4) . . ?
F1_1 C7_1 C3_1 113.8(3) . . ?
F3_1 C7_1 C3_1 113.0(3) . . ?
F2_1 C7_1 C3_1 111.1(3) . . ?
F4_1 C8_1 F6_1 109.4(4) . . ?
F4_1 C8_1 F5_1 105.7(4) . . ?
F6_1 C8_1 F5_1 102.4(4) . . ?
F4_1 C8_1 C5_1 115.0(4) . . ?
F6_1 C8_1 C5_1 113.0(4) . . ?
F5_1 C8_1 C5_1 110.4(4) . . ?
B1_1 B1_1 C9_1 119.0(4) 2_666 . ?
B1_1 B1_1 C1_1 129.5(4) 2_666 . ?
C9_1 B1_1 C1_1 111.4(3) . . ?
N2_1 C9_1 N1_1 105.3(4) . . ?
N2_1 C9_1 B1_1 127.4(4) . . ?
N1_1 C9_1 B1_1 127.3(4) . . ?
C9_1 N1_1 C10_1 109.9(4) . . ?
C9_1 N1_1 C12 123.8(5) . . ?
C10_1 N1_1 C12 126.3(5) . . ?
C11_1 C10_1 N1_1 107.5(4) . . ?
C11_1 C10_1 H10_1 126.3 . . ?
N1_1 C10_1 H10_1 126.3 . . ?
C10_1 C11_1 N2_1 106.8(4) . . ?
C10_1 C11_1 H11_1 126.6 . . ?
N2_1 C11_1 H11_1 126.6 . . ?
C9_1 N2_1 C11_1 110.5(4) . . ?
C9_1 N2_1 C15 123.1(5) . . ?
C11_1 N2_1 C15 126.0(5) . . ?
C2_2 C1_2 C6_2 120.0 . . ?
C2_2 C1_2 B1_2 125.1(14) . . ?
C6_2 C1_2 B1_2 114.9(14) . . ?
C1_2 C2_2 C3_2 120.0 . . ?
C1_2 C2_2 H2_2 120.0 . . ?
C3_2 C2_2 H2_2 120.0 . . ?
C4_2 C3_2 C2_2 120.0 . . ?
C4_2 C3_2 C7_2 113.8(16) . . ?
C2_2 C3_2 C7_2 126.2(16) . . ?
C3_2 C4_2 C5_2 120.0 . . ?
C3_2 C4_2 H4_2 120.0 . . ?
C5_2 C4_2 H4_2 120.0 . . ?
C4_2 C5_2 C6_2 120.0 . . ?
C4_2 C5_2 C8_2 118.8(16) . . ?
C6_2 C5_2 C8_2 121.2(16) . . ?
C5_2 C6_2 C1_2 120.0 . . ?
C5_2 C6_2 H6_2 120.0 . . ?
C1_2 C6_2 H6_2 120.0 . . ?
F3_2 C7_2 F1_2 115(2) . . ?
F3_2 C7_2 F2_2 117(2) . . ?
F1_2 C7_2 F2_2 97.2(19) . . ?
F3_2 C7_2 C3_2 105.0(19) . . ?
F1_2 C7_2 C3_2 115(2) . . ?
F2_2 C7_2 C3_2 107(2) . . ?
F6_2 C8_2 F4_2 107(2) . . ?
F6_2 C8_2 F5_2 107(2) . . ?
F4_2 C8_2 F5_2 109(3) . . ?
F6_2 C8_2 C5_2 116(2) . . ?
F4_2 C8_2 C5_2 109(2) . . ?
F5_2 C8_2 C5_2 108(2) . . ?
B1_2 B1_2 C9_2 111(3) 2_666 . ?
B1_2 B1_2 C1_2 136(3) 2_666 . ?
C9_2 B1_2 C1_2 114(2) . . ?
N2_2 C9_2 N1_2 103.5(18) . . ?
N2_2 C9_2 B1_2 128(3) . . ?
N1_2 C9_2 B1_2 128(3) . . ?
C9_2 N1_2 C10_2 111(2) . . ?
C9_2 N1_2 C12 121(3) . . ?
C10_2 N1_2 C12 128(3) . . ?
C11_2 C10_2 N1_2 106(2) . . ?
C11_2 C10_2 H10_2 126.9 . . ?
N1_2 C10_2 H10_2 126.9 . . ?
C10_2 C11_2 N2_2 106.5(19) . . ?
C10_2 C11_2 H11_2 126.7 . . ?
N2_2 C11_2 H11_2 126.7 . . ?
C9_2 N2_2 C11_2 111.7(19) . . ?
C9_2 N2_2 C15 131(4) . . ?
C11_2 N2_2 C15 116(3) . . ?
N1_1 C12 C14 111.3(6) . . ?
N1_1 C12 C13 110.1(6) . . ?
C14 C12 C13 112.8(4) . . ?
C14 C12 N1_2 115(5) . . ?
C13 C12 N1_2 107(5) . . ?
N1_1 C12 H12 107.5 . . ?
C14 C12 H12 107.5 . . ?
C13 C12 H12 107.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2_2 C15 C17 116(3) . . ?
N2_1 C15 C17 109.8(4) . . ?
N2_2 C15 C16 106(7) . . ?
N2_1 C15 C16 109.8(6) . . ?
C17 C15 C16 113.2(3) . . ?
N2_1 C15 H15 108.0 . . ?
C17 C15 H15 108.0 . . ?
C16 C15 H15 108.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C1_1 C2_1 1.3900 . ?
C1_1 C6_1 1.3900 . ?
C1_1 B1_1 1.634(4) . ?
C2_1 C3_1 1.3900 . ?
C2_1 H2_1 0.9500 . ?
C3_1 C4_1 1.3900 . ?
C3_1 C7_1 1.474(4) . ?
C4_1 C5_1 1.3900 . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.3900 . ?
C5_1 C8_1 1.481(5) . ?
C6_1 H6_1 0.9500 . ?
C7_1 F1_1 1.320(5) . ?
C7_1 F3_1 1.352(5) . ?
C7_1 F2_1 1.354(5) . ?
C8_1 F4_1 1.306(6) . ?
C8_1 F6_1 1.322(5) . ?
C8_1 F5_1 1.372(6) . ?
B1_1 B1_1 1.590(8) 2_666 ?
B1_1 C9_1 1.596(5) . ?
C9_1 N2_1 1.345(6) . ?
C9_1 N1_1 1.355(6) . ?
N1_1 C10_1 1.378(7) . ?
N1_1 C12 1.467(6) . ?
C10_1 C11_1 1.335(6) . ?
C10_1 H10_1 0.9500 . ?
C11_1 N2_1 1.379(8) . ?
C11_1 H11_1 0.9500 . ?
N2_1 C15 1.496(6) . ?
C1_2 C2_2 1.3900 . ?
C1_2 C6_2 1.3900 . ?
C1_2 B1_2 1.659(17) . ?
C2_2 C3_2 1.3900 . ?
C2_2 H2_2 0.9500 . ?
C3_2 C4_2 1.3900 . ?
C3_2 C7_2 1.481(17) . ?
C4_2 C5_2 1.3900 . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.3900 . ?
C5_2 C8_2 1.466(17) . ?
C6_2 H6_2 0.9500 . ?
C7_2 F3_2 1.350(19) . ?
C7_2 F1_2 1.351(19) . ?
C7_2 F2_2 1.36(2) . ?
C8_2 F6_2 1.296(19) . ?
C8_2 F4_2 1.30(2) . ?
C8_2 F5_2 1.36(2) . ?
B1_2 B1_2 1.51(6) 2_666 ?
B1_2 C9_2 1.610(18) . ?
C9_2 N2_2 1.346(19) . ?
C9_2 N1_2 1.358(19) . ?
N1_2 C10_2 1.386(19) . ?
N1_2 C12 1.54(4) . ?
C10_2 C11_2 1.33(2) . ?
C10_2 H10_2 0.9500 . ?
C11_2 N2_2 1.38(2) . ?
C11_2 H11_2 0.9500 . ?
N2_2 C15 1.41(4) . ?
C12 C14 1.503(6) . ?
C12 C13 1.506(6) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C17 1.507(6) . ?
C15 C16 1.510(6) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C6_1 C1_1 C2_1 C3_1 0.0 . . . . ?
B1_1 C1_1 C2_1 C3_1 178.9(3) . . . . ?
C1_1 C2_1 C3_1 C4_1 0.0 . . . . ?
C1_1 C2_1 C3_1 C7_1 -176.5(3) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.0 . . . . ?
C7_1 C3_1 C4_1 C5_1 176.4(3) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.0 . . . . ?
C3_1 C4_1 C5_1 C8_1 -176.4(4) . . . . ?
C4_1 C5_1 C6_1 C1_1 0.0 . . . . ?
C8_1 C5_1 C6_1 C1_1 176.5(4) . . . . ?
C2_1 C1_1 C6_1 C5_1 0.0 . . . . ?
B1_1 C1_1 C6_1 C5_1 -178.9(3) . . . . ?
C2_1 C3_1 C7_1 F1_1 -43.6(5) . . . . ?
C4_1 C3_1 C7_1 F1_1 139.9(3) . . . . ?
C2_1 C3_1 C7_1 F3_1 -165.6(3) . . . . ?
C4_1 C3_1 C7_1 F3_1 17.9(5) . . . . ?
C2_1 C3_1 C7_1 F2_1 76.8(4) . . . . ?
C4_1 C3_1 C7_1 F2_1 -99.6(4) . . . . ?
C6_1 C5_1 C8_1 F4_1 -173.8(4) . . . . ?
C4_1 C5_1 C8_1 F4_1 2.7(6) . . . . ?
C6_1 C5_1 C8_1 F6_1 59.7(5) . . . . ?
C4_1 C5_1 C8_1 F6_1 -123.9(4) . . . . ?
C6_1 C5_1 C8_1 F5_1 -54.4(5) . . . . ?
C4_1 C5_1 C8_1 F5_1 122.1(4) . . . . ?
C2_1 C1_1 B1_1 B1_1 -3.9(7) . . . 2_666 ?
C6_1 C1_1 B1_1 B1_1 175.0(5) . . . 2_666 ?
C2_1 C1_1 B1_1 C9_1 177.7(3) . . . . ?
C6_1 C1_1 B1_1 C9_1 -3.4(4) . . . . ?
B1_1 B1_1 C9_1 N2_1 -95.3(9) 2_666 . . . ?
C1_1 B1_1 C9_1 N2_1 83.3(8) . . . . ?
B1_1 B1_1 C9_1 N1_1 82.4(9) 2_666 . . . ?
C1_1 B1_1 C9_1 N1_1 -99.0(8) . . . . ?
N2_1 C9_1 N1_1 C10_1 1.0(11) . . . . ?
B1_1 C9_1 N1_1 C10_1 -177.1(5) . . . . ?
N2_1 C9_1 N1_1 C12 -179.4(10) . . . . ?
B1_1 C9_1 N1_1 C12 2.6(15) . . . . ?
C9_1 N1_1 C10_1 C11_1 -0.4(10) . . . . ?
C12 N1_1 C10_1 C11_1 180.0(9) . . . . ?
N1_1 C10_1 C11_1 N2_1 -0.4(9) . . . . ?
N1_1 C9_1 N2_1 C11_1 -1.2(12) . . . . ?
B1_1 C9_1 N2_1 C11_1 176.8(6) . . . . ?
N1_1 C9_1 N2_1 C15 -174.2(11) . . . . ?
B1_1 C9_1 N2_1 C15 3.9(15) . . . . ?
C10_1 C11_1 N2_1 C9_1 1.0(11) . . . . ?
C10_1 C11_1 N2_1 C15 173.7(9) . . . . ?
C6_2 C1_2 C2_2 C3_2 0.0 . . . . ?
B1_2 C1_2 C2_2 C3_2 -178(4) . . . . ?
C1_2 C2_2 C3_2 C4_2 0.0 . . . . ?
C1_2 C2_2 C3_2 C7_2 179(4) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.0 . . . . ?
C7_2 C3_2 C4_2 C5_2 -179(4) . . . . ?
C3_2 C4_2 C5_2 C6_2 0.0 . . . . ?
C3_2 C4_2 C5_2 C8_2 -179(4) . . . . ?
C4_2 C5_2 C6_2 C1_2 0.0 . . . . ?
C8_2 C5_2 C6_2 C1_2 179(4) . . . . ?
C2_2 C1_2 C6_2 C5_2 0.0 . . . . ?
B1_2 C1_2 C6_2 C5_2 178(4) . . . . ?
C4_2 C3_2 C7_2 F3_2 152(2) . . . . ?
C2_2 C3_2 C7_2 F3_2 -27(4) . . . . ?
C4_2 C3_2 C7_2 F1_2 24(3) . . . . ?
C2_2 C3_2 C7_2 F1_2 -155(3) . . . . ?
C4_2 C3_2 C7_2 F2_2 -83(3) . . . . ?
C2_2 C3_2 C7_2 F2_2 98(3) . . . . ?
C4_2 C5_2 C8_2 F6_2 48(3) . . . . ?
C6_2 C5_2 C8_2 F6_2 -131(3) . . . . ?
C4_2 C5_2 C8_2 F4_2 -74(3) . . . . ?
C6_2 C5_2 C8_2 F4_2 107(3) . . . . ?
C4_2 C5_2 C8_2 F5_2 167(3) . . . . ?
C6_2 C5_2 C8_2 F5_2 -12(4) . . . . ?
C2_2 C1_2 B1_2 B1_2 -11(9) . . . 2_666 ?
C6_2 C1_2 B1_2 B1_2 171(6) . . . 2_666 ?
C2_2 C1_2 B1_2 C9_2 174(3) . . . . ?
C6_2 C1_2 B1_2 C9_2 -4(4) . . . . ?
B1_2 B1_2 C9_2 N2_2 89(11) 2_666 . . . ?
C1_2 B1_2 C9_2 N2_2 -94(11) . . . . ?
B1_2 B1_2 C9_2 N1_2 -94(10) 2_666 . . . ?
C1_2 B1_2 C9_2 N1_2 83(10) . . . . ?
N2_2 C9_2 N1_2 C10_2 7(14) . . . . ?
B1_2 C9_2 N1_2 C10_2 -171(6) . . . . ?
N2_2 C9_2 N1_2 C12 -178(12) . . . . ?
B1_2 C9_2 N1_2 C12 5(17) . . . . ?
C9_2 N1_2 C10_2 C11_2 -10(12) . . . . ?
C12 N1_2 C10_2 C11_2 175(11) . . . . ?
N1_2 C10_2 C11_2 N2_2 8(11) . . . . ?
N1_2 C9_2 N2_2 C11_2 -1(15) . . . . ?
B1_2 C9_2 N2_2 C11_2 176(6) . . . . ?
N1_2 C9_2 N2_2 C15 165(15) . . . . ?
B1_2 C9_2 N2_2 C15 -18(22) . . . . ?
C10_2 C11_2 N2_2 C9_2 -5(14) . . . . ?
C10_2 C11_2 N2_2 C15 -173(9) . . . . ?
C9_1 N1_1 C12 C14 -141.5(9) . . . . ?
C10_1 N1_1 C12 C14 38.1(12) . . . . ?
C9_1 N1_1 C12 C13 92.8(10) . . . . ?
C10_1 N1_1 C12 C13 -87.6(12) . . . . ?
C9_2 N1_2 C12 C14 -115(10) . . . . ?
C10_2 N1_2 C12 C14 60(14) . . . . ?
C9_2 N1_2 C12 C13 119(11) . . . . ?
C10_2 N1_2 C12 C13 -66(13) . . . . ?
C9_2 N2_2 C15 C17 -146(13) . . . . ?
C11_2 N2_2 C15 C17 19(14) . . . . ?
C9_2 N2_2 C15 C16 87(16) . . . . ?
C11_2 N2_2 C15 C16 -107(11) . . . . ?
C9_1 N2_1 C15 C17 -133.2(9) . . . . ?
C11_1 N2_1 C15 C17 55.0(13) . . . . ?
C9_1 N2_1 C15 C16 101.7(11) . . . . ?
C11_1 N2_1 C15 C16 -70.1(11) . . . . ?
