#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:21:49 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288740 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/01/1570170.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_1570170
loop_
_publ_author_name
'Shinde, Ganesh H.'
'Ghotekar, Ganesh S.'
'Amombo Noa, Francoise M.'
'Öhrström, Lars'
'Norrby, Per-Ola'
'Sundén, Henrik'
_publ_section_title
;
 Regioselective ortho halogenation of N-aryl amides and
 ureas via oxidative halodeboronation: harnessing boron reactivity
 for efficient C-halogen bond installation.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              13429
_journal_page_last               13436
_journal_paper_doi               10.1039/d3sc04628a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C11 H14 B F2 N O'
_chemical_formula_sum            'C11 H14 B F2 N O'
_chemical_formula_weight         225.04
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-07-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-12 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4333(2)
_cell_length_b                   11.2099(3)
_cell_length_c                   15.6487(5)
_cell_measurement_reflns_used    4281
_cell_measurement_temperature    101(3)
_cell_measurement_theta_max      75.2860
_cell_measurement_theta_min      4.8470
_cell_volume                     1128.53(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      101(3)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -123.00 -29.00   0.50    2.21    --  -43.19 -16.00 -23.00  188
  2  ω     15.00  88.00   0.50    2.21    --   43.19-118.00-110.00  146
  3  ω     33.00 123.00   0.50    2.21    --   43.19  16.00 146.00  180
  4  ω   -136.00 -90.00   0.50    8.82    -- -104.50 -16.00 -23.00   92
  5  ω     33.00  97.00   0.50    8.82    --  108.62-115.00 156.00  128
  6  ω     94.00 143.00   0.50    8.82    --  108.62  16.00 146.00   98
  7  ω     33.00  97.00   0.50    8.82    --  108.62-118.00-110.00  128
  8  ω    -15.00  34.00   0.50    2.21    --  -43.19  38.00-180.00   98
  9  ω    -72.00 -30.00   0.50    8.82    -- -104.50  77.00   0.00   84
 10  ω   -132.00 -89.00   0.50    8.82    -- -104.50 -15.00-180.00   86
 11  ω   -174.00 -91.00   0.50    8.82    -- -104.50 -52.00   4.66  166
 12  ω    -72.00 -30.00   0.50    8.82    -- -104.50  77.00-120.00   84
 13  ω   -132.00 -89.00   0.50    8.82    -- -104.50 -15.00-150.00   86
 14  ω    -72.00 -30.00   0.50    8.82    -- -104.50  77.00  60.00   84
 15  ω   -101.00 -31.00   0.50    8.82    -- -104.50 125.00-180.00  140
 16  ω   -132.00 -89.00   0.50    8.82    -- -104.50 -15.00 -90.00   86
 17  ω    -72.00 -30.00   0.50    8.82    -- -104.50  77.00  90.00   84
 18  ω    -92.00 -31.00   0.50    8.82    -- -104.50  92.00-107.02  122
 19  ω     34.00  92.00   0.50    8.82    --  108.62 -95.00 -60.00  116
 20  ω     35.00  79.00   0.50    8.82    --  108.62 -77.00 -60.00   88
 21  ω    -54.00 -28.00   0.50    2.21    --  -43.19 -59.00  24.01   52
 22  ω    -54.00 -28.00   0.50    2.21    --  -43.19 -57.00 144.93   52
 23  ω    -54.00 -28.00   0.50    2.21    --  -43.19 -58.00 -59.78   52
 24  ω    -54.00 -28.00   0.50    2.21    --  -43.19 -56.00-142.05   52
 25  ω    -54.00 -28.00   0.50    2.21    --  -43.19 -59.00 -99.43   52
 26  ω    -15.00  34.00   0.50    2.21    --  -43.19  38.00  90.00   98
 27  ω   -132.00 -91.00   0.50    8.82    -- -104.50 -15.00 -60.00   82
 28  ω   -132.00 -89.00   0.50    8.82    -- -104.50 -15.00-120.00   86
 29  ω   -132.00 -89.00   0.50    8.82    -- -104.50 -15.00 150.00   86
 30  ω     94.00 139.00   0.50    8.82    --  108.62  15.00  90.00   90
 31  ω     94.00 139.00   0.50    8.82    --  108.62  15.00 120.00   90
 32  ω     94.00 139.00   0.50    8.82    --  108.62  15.00  60.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10669
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.623
_diffrn_reflns_theta_min         4.853
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 601 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2261
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0921
_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)+(0.0681P)²+2.5060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2193
_refine_ls_wR_factor_ref         0.2244
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                1972
_reflns_number_total             2261
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04628a2.cif
_cod_data_source_block           ggothersolvent_auto
_cod_depositor_comments          'Adding full bibliography for 1570170.cif.'
_cod_database_code               1570170
_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_max   0.982
_shelx_estimated_absorpt_t_min   0.801
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C1A \\sim C7-C1B
 with sigma of 0.02
 C7-C2A \\sim C7-C2B
 with sigma of 0.02
 C7-C3A \\sim C7-C3B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C1B, C2B, C3B, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1A, C2A, C3A, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(H2BC)=
 Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(H3BC)=1-FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C12(H12), C13(H13), C14(H14)
5.b Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC), C2A(H2AA,H2AB,H2AC), C2B(H2BA,H2BB,
 H2BC), C3A(H3AA,H3AB,H3AC), C3B(H3BA,H3BB,H3BC)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.0088(6) 0.3192(3) 0.4422(3) 0.0612(13) Uani 1 1 d . . . . .
F2 F -0.0067(7) 0.4520(4) 0.3339(3) 0.0703(14) Uani 1 1 d . . . . .
O1 O 0.2447(7) 0.3023(4) 0.3342(4) 0.0582(15) Uani 1 1 d . . . . .
N1 N 0.5501(7) 0.3363(5) 0.3997(3) 0.0355(11) Uani 1 1 d . . . . .
H1 H 0.676150 0.312807 0.406716 0.043 Uiso 1 1 calc R U . . .
C1A C 0.446(3) 0.2198(12) 0.1987(8) 0.052(4) Uani 0.537(16) 1 d D . P A 1
H1AA H 0.296679 0.216499 0.198639 0.079 Uiso 0.537(16) 1 calc R U P A 1
H1AB H 0.499259 0.166051 0.156284 0.079 Uiso 0.537(16) 1 calc R U P A 1
H1AC H 0.490186 0.299586 0.185805 0.079 Uiso 0.537(16) 1 calc R U P A 1
C1B C 0.356(4) 0.099(2) 0.2557(14) 0.076(7) Uani 0.463(16) 1 d D . P A 2
H1BA H 0.347072 0.031979 0.293496 0.115 Uiso 0.463(16) 1 calc R U P A 2
H1BB H 0.388212 0.072055 0.199021 0.115 Uiso 0.463(16) 1 calc R U P A 2
H1BC H 0.225448 0.140655 0.255088 0.115 Uiso 0.463(16) 1 calc R U P A 2
C2A C 0.425(2) 0.0647(11) 0.3100(12) 0.051(4) Uani 0.537(16) 1 d D . P A 1
H2AA H 0.498393 0.028888 0.356838 0.077 Uiso 0.537(16) 1 calc R U P A 1
H2AB H 0.428814 0.012224 0.261574 0.077 Uiso 0.537(16) 1 calc R U P A 1
H2AC H 0.282913 0.078384 0.326320 0.077 Uiso 0.537(16) 1 calc R U P A 1
C2B C 0.701(4) 0.1111(17) 0.3318(12) 0.067(6) Uani 0.463(16) 1 d D . P A 2
H2BA H 0.808759 0.164324 0.350699 0.101 Uiso 0.463(16) 1 calc R U P A 2
H2BB H 0.758718 0.054313 0.292370 0.101 Uiso 0.463(16) 1 calc R U P A 2
H2BC H 0.643949 0.069808 0.380043 0.101 Uiso 0.463(16) 1 calc R U P A 2
C3A C 0.760(2) 0.1757(17) 0.2950(13) 0.065(5) Uani 0.537(16) 1 d D . P A 1
H3AA H 0.820026 0.253480 0.287512 0.097 Uiso 0.537(16) 1 calc R U P A 1
H3AB H 0.813807 0.122695 0.252129 0.097 Uiso 0.537(16) 1 calc R U P A 1
H3AC H 0.795431 0.145815 0.350641 0.097 Uiso 0.537(16) 1 calc R U P A 1
C3B C 0.624(3) 0.2437(15) 0.2081(10) 0.051(5) Uani 0.463(16) 1 d D . P A 2
H3BA H 0.518204 0.286762 0.177622 0.077 Uiso 0.463(16) 1 calc R U P A 2
H3BB H 0.682667 0.183930 0.171441 0.077 Uiso 0.463(16) 1 calc R U P A 2
H3BC H 0.730677 0.297920 0.226017 0.077 Uiso 0.463(16) 1 calc R U P A 2
C7 C 0.5274(11) 0.1837(5) 0.2867(4) 0.0438(15) Uani 1 1 d D . . . .
C8 C 0.4371(9) 0.2790(5) 0.3452(4) 0.0318(12) Uani 1 1 d . . . . .
C9 C 0.4813(10) 0.4358(5) 0.4491(4) 0.0383(13) Uani 1 1 d . . . . .
C10 C 0.2748(11) 0.4700(5) 0.4427(5) 0.0474(18) Uani 1 1 d . . . . .
C11 C 0.2198(14) 0.5739(7) 0.4881(7) 0.075(3) Uani 1 1 d . . . . .
H11 H 0.082956 0.600263 0.484959 0.090 Uiso 1 1 calc R U . . .
C12 C 0.3540(17) 0.6363(7) 0.5353(7) 0.084(4) Uani 1 1 d . . . . .
H12 H 0.311675 0.705874 0.562569 0.100 Uiso 1 1 calc R U . . .
C13 C 0.5560(17) 0.5968(8) 0.5432(6) 0.075(3) Uani 1 1 d . . . . .
H13 H 0.648929 0.637790 0.578000 0.090 Uiso 1 1 calc R U . . .
C14 C 0.6207(13) 0.4960(8) 0.4994(5) 0.058(2) Uani 1 1 d . . . . .
H14 H 0.757241 0.469467 0.504057 0.070 Uiso 1 1 calc R U . . .
B1 B 0.1187(12) 0.3902(8) 0.3899(7) 0.055(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C8 O1 B1 124.3(6) . . ?
C8 N1 H1 117.5 . . ?
C8 N1 C9 124.9(5) . . ?
C9 N1 H1 117.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C7 C1A H1AA 109.5 . . ?
C7 C1A H1AB 109.5 . . ?
C7 C1A H1AC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
C7 C1B H1BA 109.5 . . ?
C7 C1B H1BB 109.5 . . ?
C7 C1B H1BC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
C7 C2A H2AA 109.5 . . ?
C7 C2A H2AB 109.5 . . ?
C7 C2A H2AC 109.5 . . ?
H2BA C2B H2BB 109.5 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?
C7 C2B H2BA 109.5 . . ?
C7 C2B H2BB 109.5 . . ?
C7 C2B H2BC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C7 C3A H3AA 109.5 . . ?
C7 C3A H3AB 109.5 . . ?
C7 C3A H3AC 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
C7 C3B H3BA 109.5 . . ?
C7 C3B H3BB 109.5 . . ?
C7 C3B H3BC 109.5 . . ?
C1A C7 C2A 107.3(10) . . ?
C1B C7 C2B 109.8(14) . . ?
C3A C7 C1A 115.8(11) . . ?
C3A C7 C2A 110.8(11) . . ?
C3A C7 C8 111.7(8) . . ?
C3B C7 C1B 107.9(12) . . ?
C3B C7 C2B 107.6(12) . . ?
C8 C7 C1A 103.0(7) . . ?
C8 C7 C1B 110.5(9) . . ?
C8 C7 C2A 107.6(8) . . ?
C8 C7 C2B 111.7(8) . . ?
C8 C7 C3B 109.2(8) . . ?
O1 C8 N1 122.1(6) . . ?
O1 C8 C7 115.7(6) . . ?
N1 C8 C7 122.1(5) . . ?
C10 C9 N1 118.3(6) . . ?
C14 C9 N1 119.5(6) . . ?
C14 C9 C10 122.2(7) . . ?
C9 C10 C11 115.7(7) . . ?
C9 C10 B1 119.4(6) . . ?
C11 C10 B1 124.9(7) . . ?
C10 C11 H11 118.3 . . ?
C12 C11 C10 123.4(9) . . ?
C12 C11 H11 118.3 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(8) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(9) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 119.3(8) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
F1 B1 O1 105.8(6) . . ?
F1 B1 C10 112.8(8) . . ?
F2 B1 F1 108.3(6) . . ?
F2 B1 O1 105.6(8) . . ?
F2 B1 C10 114.9(6) . . ?
O1 B1 C10 108.8(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.406(9) . ?
F2 B1 1.377(10) . ?
O1 C8 1.277(7) . ?
O1 B1 1.545(11) . ?
N1 H1 0.8600 . ?
N1 C8 1.292(8) . ?
N1 C9 1.427(8) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C1A C7 1.529(14) . ?
C1B H1BA 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1BC 0.9600 . ?
C1B C7 1.532(17) . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C2A C7 1.533(13) . ?
C2B H2BA 0.9600 . ?
C2B H2BB 0.9600 . ?
C2B H2BC 0.9600 . ?
C2B C7 1.553(17) . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?
C3A C7 1.507(15) . ?
C3B H3BA 0.9600 . ?
C3B H3BB 0.9600 . ?
C3B H3BC 0.9600 . ?
C3B C7 1.532(14) . ?
C7 C8 1.522(9) . ?
C9 C10 1.387(9) . ?
C9 C14 1.370(10) . ?
C10 C11 1.408(11) . ?
C10 B1 1.579(13) . ?
C11 H11 0.9300 . ?
C11 C12 1.335(14) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(11) . ?
C14 H14 0.9300 . ?
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
N1 C9 C10 C11 -175.5(6) . . . . ?
N1 C9 C10 B1 6.9(10) . . . . ?
N1 C9 C14 C13 176.1(7) . . . . ?
C1A C7 C8 O1 46.4(9) . . . . ?
C1A C7 C8 N1 -130.6(8) . . . . ?
C1B C7 C8 O1 -25.1(14) . . . . ?
C1B C7 C8 N1 157.9(12) . . . . ?
C2A C7 C8 O1 -66.8(10) . . . . ?
C2A C7 C8 N1 116.2(9) . . . . ?
C2B C7 C8 O1 -147.5(11) . . . . ?
C2B C7 C8 N1 35.5(12) . . . . ?
C3A C7 C8 O1 171.3(11) . . . . ?
C3A C7 C8 N1 -5.6(12) . . . . ?
C3B C7 C8 O1 93.5(10) . . . . ?
C3B C7 C8 N1 -83.5(10) . . . . ?
C8 O1 B1 F1 -105.9(8) . . . . ?
C8 O1 B1 F2 139.4(7) . . . . ?
C8 O1 B1 C10 15.6(10) . . . . ?
C8 N1 C9 C10 4.1(9) . . . . ?
C8 N1 C9 C14 -174.3(6) . . . . ?
C9 N1 C8 O1 -4.5(10) . . . . ?
C9 N1 C8 C7 172.3(5) . . . . ?
C9 C10 C11 C12 -0.6(13) . . . . ?
C9 C10 B1 F1 102.2(8) . . . . ?
C9 C10 B1 F2 -133.1(7) . . . . ?
C9 C10 B1 O1 -14.9(10) . . . . ?
C10 C9 C14 C13 -2.2(11) . . . . ?
C10 C11 C12 C13 -2.2(15) . . . . ?
C11 C10 B1 F1 -75.1(9) . . . . ?
C11 C10 B1 F2 49.6(12) . . . . ?
C11 C10 B1 O1 167.7(7) . . . . ?
C11 C12 C13 C14 2.8(14) . . . . ?
C12 C13 C14 C9 -0.7(13) . . . . ?
C14 C9 C10 C11 2.8(10) . . . . ?
C14 C9 C10 B1 -174.8(7) . . . . ?
B1 O1 C8 N1 -6.8(10) . . . . ?
B1 O1 C8 C7 176.2(6) . . . . ?
B1 C10 C11 C12 176.9(9) . . . . ?
