#------------------------------------------------------------------------------
#$Date: 2015-09-14 10:51:50 +0300 (Mon, 14 Sep 2015) $
#$Revision: 156301 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/77/7117788.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_7117788
loop_
_publ_author_name
'Jeffrey M. Farrell'
'Douglas W. Stephan'
_publ_section_title
;
 Synthesis of a diboryl-N-heterocycle and its conversion to a bidentate
 cationic Lewis acid
;
_journal_name_full               Chem.Commun.
_journal_page_first              14322
_journal_paper_doi               10.1039/C5cc06248A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'B C24 F20, C20 H32 B2 N2'
_chemical_formula_sum            'C44 H32 B3 F20 N2'
_chemical_formula_weight         1001.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_date             2015-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-21 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2516(9)
_cell_length_b                   17.7060(9)
_cell_length_c                   27.4233(14)
_cell_measurement_reflns_used    9644
_cell_measurement_temperature    149
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.42
_cell_volume                     8376.6(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      149.7
_diffrn_measured_fraction_theta_full 0.9999
_diffrn_measured_fraction_theta_max 0.9999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            90800
_diffrn_reflns_theta_full        24.9991
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5876
_exptl_crystal_density_meas      .
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             4043.7039
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.0959
_refine_diff_density_min         -0.4880
_refine_diff_density_rms         0.0896
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             11.2655
_refine_ls_goodness_of_fit_ref   1.0735
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    51
_refine_ls_number_parameters     621
_refine_ls_number_reflns         7379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0735
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0750
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0703P)²+29.0718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.1942
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              0
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                6629
_reflns_number_total             7379
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5cc06248a2.cif
_cod_data_source_block           jf049_0ma
_cod_original_cell_volume        8376.6(8)
_cod_database_code               7117788
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C9(H9), C17(H17), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b), C20(H20a,H20b), C10(H10a,H10b), C11(H11a,H11b), C14(H14a,
 H14b), C18(H18a,H18b), C16(H16a,H16b), C8(H8a,H8b), C7(H7a,H7b), C6(H6a,H6b),
 C12(H12a,H12b)
2.c Me refined with riding coordinates:
 C4(H4a,H4b,H4c)
2.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C2(H2), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-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_refinement_flags_posn
F13 F 0.48607(15) 0.54919(14) 0.10199(10) 0.0505(7) Uani 1.000000 .
F3 F 0.60242(16) 0.20198(16) 0.38771(9) 0.0544(7) Uani 1.000000 .
F1 F 0.55244(13) 0.27259(13) 0.22652(8) 0.0384(5) Uani 1.000000 .
F4 F 0.74043(15) 0.27641(15) 0.38433(8) 0.0458(6) Uani 1.000000 .
F5 F 0.78373(13) 0.35029(14) 0.30502(8) 0.0379(5) Uani 1.000000 .
F15 F 0.54917(13) 0.42812(13) 0.24768(8) 0.0382(5) Uani 1.000000 .
F14 F 0.45742(15) 0.51858(15) 0.19685(11) 0.0539(7) Uani 1.000000 .
F12 F 0.61095(14) 0.48464(13) 0.05757(8) 0.0406(6) Uani 1.000000 .
F11 F 0.70338(13) 0.39159(12) 0.10657(7) 0.0342(5) Uani 1.000000 .
F18 F 0.76056(18) 0.05579(13) 0.12082(10) 0.0555(7) Uani 1.000000 .
F17 F 0.63287(18) 0.13377(14) 0.09275(9) 0.0546(7) Uani 1.000000 .
F16 F 0.60254(14) 0.26837(12) 0.12852(8) 0.0404(6) Uani 1.000000 .
F19 F 0.85769(15) 0.11663(15) 0.18945(10) 0.0542(7) Uani 1.000000 .
F20 F 0.82802(13) 0.25275(14) 0.22670(8) 0.0411(6) Uani 1.000000 .
F10 F 0.85031(14) 0.35356(16) 0.14923(9) 0.0503(7) Uani 1.000000 .
F7 F 0.80562(18) 0.59403(14) 0.26840(10) 0.0576(8) Uani 1.000000 .
F6 F 0.70220(14) 0.48219(13) 0.26848(8) 0.0389(5) Uani 1.000000 .
F2 F 0.50792(15) 0.20214(16) 0.30752(10) 0.0538(7) Uani 1.000000 .
C19 C 0.2009(3) 0.0168(4) 0.0602(3) 0.0769(18) Uani 1.000000 .
H19a H 0.1460(3) 0.0249(4) 0.0692(3) 0.092(2) Uiso 1.000000 R
H19b H 0.2028(3) -0.0251(4) 0.0363(3) 0.092(2) Uiso 1.000000 R
C20 C 0.2323(3) 0.0882(3) 0.0365(2) 0.0665(15) Uani 1.000000 .
H20a H 0.2045(3) 0.0967(3) 0.0054(2) 0.0798(18) Uiso 1.000000 R
H20b H 0.2212(3) 0.1317(3) 0.0581(2) 0.0798(18) Uiso 1.000000 R
C13 C 0.3193(3) 0.0859(3) 0.02622(17) 0.0451(10) Uani 1.000000 .
H13 H 0.3368(3) 0.1356(3) 0.01286(17) 0.0542(12) Uiso 1.000000 R
B2 B 0.3545(3) 0.0734(3) 0.07776(17) 0.0375(10) Uani 1.000000 .
N1 N 0.38605(19) 0.1332(2) 0.10906(12) 0.0378(8) Uani 1.000000 .
C1 C 0.4037(2) 0.2061(2) 0.09611(13) 0.0356(9) Uani 1.000000 .
B1 B 0.4118(3) 0.2395(3) 0.04271(16) 0.0343(10) Uani 1.000000 .
C9 C 0.4657(3) 0.2039(2) 0.00397(14) 0.0438(10) Uani 1.000000 .
H9 H 0.4794(3) 0.1511(2) 0.01369(14) 0.0526(12) Uiso 1.000000 R
C10 C 0.4366(3) 0.2048(3) -0.04850(16) 0.0546(13) Uani 1.000000 .
H10a H 0.4821(3) 0.2048(3) -0.07052(16) 0.0655(15) Uiso 1.000000 R
H10b H 0.4076(3) 0.1575(3) -0.05449(16) 0.0655(15) Uiso 1.000000 R
C11 C 0.3842(4) 0.2719(3) -0.06232(18) 0.0697(17) Uani 1.000000 .
H11a H 0.4174(4) 0.3132(3) -0.07469(18) 0.084(2) Uiso 1.000000 R
H11b H 0.3500(4) 0.2559(3) -0.08939(18) 0.084(2) Uiso 1.000000 R
C15 C 0.3863(5) -0.0388(4) 0.0135(3) 0.095(2) Uani 1.000000 .
H15 H 0.4323(5) -0.0576(4) -0.0012(3) 0.114(3) Uiso 1.000000 R
C14 C 0.3416(4) 0.0211(3) -0.00971(18) 0.0595(14) Uani 1.000000 .
H14a H 0.2937(4) -0.0007(3) -0.02367(18) 0.0714(16) Uiso 1.000000 R
H14b H 0.3723(4) 0.0426(3) -0.03689(18) 0.0714(16) Uiso 1.000000 R
C18 C 0.2462(4) -0.0058(4) 0.1054(2) 0.0744(18) Uani 1.000000 .
H18a H 0.2352(4) 0.0313(4) 0.1315(2) 0.089(2) Uiso 1.000000 R
H18b H 0.2272(4) -0.0556(4) 0.1166(2) 0.089(2) Uiso 1.000000 R
C17 C 0.3353(3) -0.0106(3) 0.09834(19) 0.0598(13) Uani 1.000000 .
H17 H 0.3620(3) -0.0197(3) 0.13017(19) 0.0717(16) Uiso 1.000000 R
C16 C 0.3581(5) -0.0703(3) 0.0610(2) 0.0807(19) Uani 1.000000 .
H16a H 0.3126(5) -0.1030(3) 0.0547(2) 0.097(2) Uiso 1.000000 R
H16b H 0.3993(5) -0.1023(3) 0.0752(2) 0.097(2) Uiso 1.000000 R
C2 C 0.3902(3) 0.1276(3) 0.15948(14) 0.0447(11) Uani 1.000000 .
H2 H 0.3809(3) 0.0836(3) 0.17834(14) 0.0537(13) Uiso 1.000000 R
C3 C 0.4089(2) 0.1931(3) 0.17597(16) 0.0458(11) Uani 1.000000 .
H3 H 0.4164(2) 0.2053(3) 0.20938(16) 0.0550(13) Uiso 1.000000 R
N2 N 0.4163(2) 0.2418(2) 0.13821(13) 0.0407(8) Uani 1.000000 .
C8 C 0.5370(3) 0.2565(3) 0.01123(18) 0.0536(12) Uani 1.000000 .
H8a H 0.5525(3) 0.2554(3) 0.04599(18) 0.0644(14) Uiso 1.000000 R
H8b H 0.5809(3) 0.2367(3) -0.00818(18) 0.0644(14) Uiso 1.000000 R
C7 C 0.5221(3) 0.3369(3) -0.00342(19) 0.0582(13) Uani 1.000000 .
H7a H 0.5673(3) 0.3680(3) 0.00610(19) 0.0698(16) Uiso 1.000000 R
H7b H 0.5174(3) 0.3393(3) -0.03936(19) 0.0698(16) Uiso 1.000000 R
C6 C 0.4476(4) 0.3716(2) 0.01983(17) 0.0577(14) Uani 1.000000 .
H6a H 0.4614(4) 0.3923(2) 0.05224(17) 0.0692(17) Uiso 1.000000 R
H6b H 0.4305(4) 0.4145(2) -0.00072(17) 0.0692(17) Uiso 1.000000 R
C5 C 0.3787(3) 0.3172(3) 0.02623(16) 0.0485(11) Uani 1.000000 .
H5 H 0.3422(3) 0.3372(3) 0.05149(16) 0.0582(13) Uiso 1.000000 R
C12 C 0.3346(4) 0.3025(4) -0.02202(19) 0.0706(17) Uani 1.000000 .
H12a H 0.3109(4) 0.3505(4) -0.03308(19) 0.085(2) Uiso 1.000000 R
H12b H 0.2920(4) 0.2664(4) -0.01559(19) 0.085(2) Uiso 1.000000 R
C4 C 0.4344(3) 0.3209(3) 0.14267(17) 0.0467(11) Uani 1.000000 .
H4a H 0.4411(3) 0.3338(3) 0.17717(17) 0.0701(16) Uiso 1.000000 R
H4b H 0.4824(3) 0.3319(3) 0.12492(17) 0.0701(16) Uiso 1.000000 R
H4c H 0.3919(3) 0.3509(3) 0.12896(17) 0.0701(16) Uiso 1.000000 R
F8 F 0.93132(19) 0.58797(19) 0.20806(13) 0.0760(10) Uani 1.000000 .
C30 C 0.8797(3) 0.5310(3) 0.20903(18) 0.0520(13) Uani 1.000000 .
C29 C 0.8167(3) 0.5337(2) 0.23911(16) 0.0448(11) Uani 1.000000 .
C28 C 0.7643(2) 0.4745(2) 0.23855(14) 0.0337(9) Uani 1.000000 .
C27 C 0.7703(2) 0.4106(2) 0.20981(13) 0.0311(8) Uani 1.000000 .
C33 C 0.6307(2) 0.40259(18) 0.17961(12) 0.0233(7) Uani 1.000000 .
C38 C 0.5675(2) 0.4386(2) 0.20037(13) 0.0268(7) Uani 1.000000 .
C37 C 0.5182(2) 0.4863(2) 0.17497(15) 0.0339(9) Uani 1.000000 .
C36 C 0.5323(2) 0.5015(2) 0.12678(15) 0.0325(8) Uani 1.000000 .
C24 C 0.6236(2) 0.2391(2) 0.34697(14) 0.0365(9) Uani 1.000000 .
C23 C 0.5763(2) 0.2393(2) 0.30678(15) 0.0363(9) Uani 1.000000 .
C22 C 0.6004(2) 0.2771(2) 0.26549(13) 0.0297(8) Uani 1.000000 .
C21 C 0.6694(2) 0.3175(2) 0.26108(12) 0.0264(7) Uani 1.000000 .
C26 C 0.7140(2) 0.3152(2) 0.30326(13) 0.0284(8) Uani 1.000000 .
C25 C 0.6926(2) 0.2771(2) 0.34485(13) 0.0329(8) Uani 1.000000 .
C35 C 0.5951(2) 0.4687(2) 0.10443(13) 0.0287(8) Uani 1.000000 .
C34 C 0.6416(2) 0.42112(19) 0.13108(13) 0.0257(7) Uani 1.000000 .
C39 C 0.7155(2) 0.2704(2) 0.17853(12) 0.0266(7) Uani 1.000000 .
C44 C 0.7788(2) 0.2266(2) 0.19243(13) 0.0308(8) Uani 1.000000 .
C43 C 0.7949(2) 0.1557(2) 0.17387(15) 0.0381(10) Uani 1.000000 .
C42 C 0.7470(3) 0.1247(2) 0.13978(15) 0.0377(9) Uani 1.000000 .
C41 C 0.6825(3) 0.1643(2) 0.12517(14) 0.0366(9) Uani 1.000000 .
C40 C 0.6685(2) 0.2349(2) 0.14472(13) 0.0296(8) Uani 1.000000 .
C31 C 0.8895(2) 0.4695(3) 0.17961(18) 0.0516(12) Uani 1.000000 .
F9 F 0.95199(17) 0.4653(2) 0.14958(13) 0.0775(10) Uani 1.000000 .
C32 C 0.8358(2) 0.4108(2) 0.18047(15) 0.0385(9) Uani 1.000000 .
B3 B 0.6968(2) 0.3507(2) 0.20747(14) 0.0258(8) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
H19b C19 H19a 107.8 . .
C20 C19 H19a 109.1(3) . .
C20 C19 H19b 109.1(4) . .
C18 C19 H19a 109.1(3) . .
C18 C19 H19b 109.1(4) . .
C18 C19 C20 112.6(5) . .
H20a C20 C19 108.8(3) . .
H20b C20 C19 108.8(3) . .
H20b C20 H20a 107.7 . .
C13 C20 C19 114.0(5) . .
C13 C20 H20a 108.8(3) . .
C13 C20 H20b 108.8(3) . .
H13 C13 C20 109.9(3) . .
B2 C13 C20 102.7(4) . .
B2 C13 H13 109.9(3) . .
C14 C13 C20 112.3(4) . .
C14 C13 H13 109.9(3) . .
C14 C13 B2 111.9(4) . .
N1 B2 C13 125.0(4) . .
C17 B2 C13 111.5(4) . .
C17 B2 N1 122.2(4) . .
C1 N1 B2 127.5(3) . .
C2 N1 B2 123.4(4) . .
C2 N1 C1 108.2(4) . .
B1 C1 N1 127.5(3) . .
N2 C1 N1 105.0(3) . .
N2 C1 B1 127.4(4) . .
C9 B1 C1 122.4(4) . .
C5 B1 C1 124.4(4) . .
C5 B1 C9 112.4(4) . .
H9 C9 B1 109.8(2) . .
C10 C9 B1 116.5(4) . .
C10 C9 H9 109.8(2) . .
C8 C9 B1 98.3(3) . .
C8 C9 H9 109.8(3) . .
C8 C9 C10 112.0(4) . .
H10a C10 C9 108.4(3) . .
H10b C10 C9 108.4(3) . .
H10b C10 H10a 107.4 . .
C11 C10 C9 115.7(4) . .
C11 C10 H10a 108.4(3) . .
C11 C10 H10b 108.4(3) . .
H11a C11 C10 108.4(3) . .
H11b C11 C10 108.4(3) . .
H11b C11 H11a 107.4 . .
C12 C11 C10 115.7(4) . .
C12 C11 H11a 108.4(4) . .
C12 C11 H11b 108.4(3) . .
C14 C15 H15 120.7(4) . .
C16 C15 H15 120.7(4) . .
C16 C15 C14 118.6(6) . .
C15 C14 C13 113.0(4) . .
H14a C14 C13 109.0(3) . .
H14a C14 C15 109.0(4) . .
H14b C14 C13 109.0(3) . .
H14b C14 C15 109.0(4) . .
H14b C14 H14a 107.8 . .
H18a C18 C19 108.5(4) . .
H18b C18 C19 108.5(3) . .
H18b C18 H18a 107.5 . .
C17 C18 C19 115.0(5) . .
C17 C18 H18a 108.5(3) . .
C17 C18 H18b 108.5(3) . .
C18 C17 B2 101.2(4) . .
H17 C17 B2 110.9(3) . .
H17 C17 C18 110.9(3) . .
C16 C17 B2 110.4(4) . .
C16 C17 C18 112.2(5) . .
C16 C17 H17 110.9(3) . .
C17 C16 C15 114.3(5) . .
H16a C16 C15 108.7(4) . .
H16a C16 C17 108.7(4) . .
H16b C16 C15 108.7(4) . .
H16b C16 C17 108.7(3) . .
H16b C16 H16a 107.6 . .
H2 C2 N1 126.3(3) . .
C3 C2 N1 107.5(4) . .
C3 C2 H2 126.3(3) . .
H3 C3 C2 125.4(3) . .
N2 C3 C2 109.2(4) . .
N2 C3 H3 125.4(3) . .
C3 N2 C1 110.1(4) . .
C4 N2 C1 124.8(4) . .
C4 N2 C3 125.1(4) . .
H8a C8 C9 108.9(2) . .
H8b C8 C9 108.9(2) . .
H8b C8 H8a 107.7 . .
C7 C8 C9 113.4(4) . .
C7 C8 H8a 108.9(3) . .
C7 C8 H8b 108.9(3) . .
H7a C7 C8 108.8(3) . .
H7b C7 C8 108.8(3) . .
H7b C7 H7a 107.7 . .
C6 C7 C8 113.9(4) . .
C6 C7 H7a 108.8(3) . .
C6 C7 H7b 108.8(3) . .
H6a C6 C7 108.3(3) . .
H6b C6 C7 108.3(3) . .
H6b C6 H6a 107.4 . .
C5 C6 C7 115.8(4) . .
C5 C6 H6a 108.3(2) . .
C5 C6 H6b 108.3(3) . .
C6 C5 B1 107.6(4) . .
H5 C5 B1 110.0(2) . .
H5 C5 C6 110.0(2) . .
C12 C5 B1 106.3(4) . .
C12 C5 C6 112.8(4) . .
C12 C5 H5 110.0(3) . .
C5 C12 C11 114.2(5) . .
H12a C12 C11 108.7(3) . .
H12a C12 C5 108.7(3) . .
H12b C12 C11 108.7(4) . .
H12b C12 C5 108.7(3) . .
H12b C12 H12a 107.6 . .
H4a C4 N2 109.5 . .
H4b C4 N2 109.5 . .
H4b C4 H4a 109.5 . .
H4c C4 N2 109.5 . .
H4c C4 H4a 109.5 . .
H4c C4 H4b 109.5 . .
C29 C30 F8 120.8(5) . .
C31 C30 F8 120.3(5) . .
C31 C30 C29 118.9(4) . .
C30 C29 F7 120.0(4) . .
C28 C29 F7 120.8(4) . .
C28 C29 C30 119.2(4) . .
C29 C28 F6 115.7(4) . .
C27 C28 F6 119.0(3) . .
C27 C28 C29 125.2(4) . .
C32 C27 C28 112.9(4) . .
B3 C27 C28 119.3(3) . .
B3 C27 C32 127.1(4) . .
C34 C33 C38 113.1(3) . .
B3 C33 C38 127.5(3) . .
B3 C33 C34 118.9(3) . .
C33 C38 F15 121.1(3) . .
C37 C38 F15 115.1(3) . .
C37 C38 C33 123.8(3) . .
C38 C37 F14 121.1(4) . .
C36 C37 F14 119.2(3) . .
C36 C37 C38 119.8(3) . .
C37 C36 F13 120.4(4) . .
C35 C36 F13 120.5(3) . .
C35 C36 C37 119.1(3) . .
C23 C24 F3 120.5(4) . .
C25 C24 F3 120.7(4) . .
C25 C24 C23 118.8(3) . .
C24 C23 F2 120.4(3) . .
C22 C23 F2 120.8(4) . .
C22 C23 C24 118.8(4) . .
C23 C22 F1 115.8(3) . .
C21 C22 F1 118.9(3) . .
C21 C22 C23 125.3(3) . .
C26 C21 C22 112.7(3) . .
B3 C21 C22 120.3(3) . .
B3 C21 C26 126.3(3) . .
C21 C26 F5 120.5(3) . .
C25 C26 F5 115.7(3) . .
C25 C26 C21 123.8(3) . .
C24 C25 F4 119.3(3) . .
C26 C25 F4 120.1(3) . .
C26 C25 C24 120.6(3) . .
C36 C35 F12 120.0(3) . .
C34 C35 F12 121.2(3) . .
C34 C35 C36 118.8(3) . .
C33 C34 F11 119.3(3) . .
C35 C34 F11 115.4(3) . .
C35 C34 C33 125.3(3) . .
C40 C39 C44 112.9(3) . .
B3 C39 C44 119.9(3) . .
B3 C39 C40 126.6(3) . .
C39 C44 F20 119.5(3) . .
C43 C44 F20 116.2(3) . .
C43 C44 C39 124.3(4) . .
C44 C43 F19 120.6(4) . .
C42 C43 F19 119.7(4) . .
C42 C43 C44 119.7(4) . .
C43 C42 F18 121.6(4) . .
C41 C42 F18 119.4(4) . .
C41 C42 C43 119.0(4) . .
C42 C41 F17 120.1(3) . .
C40 C41 F17 120.5(4) . .
C40 C41 C42 119.4(4) . .
C39 C40 F16 120.9(3) . .
C41 C40 F16 114.5(3) . .
C41 C40 C39 124.6(3) . .
F9 C31 C30 120.0(4) . .
C32 C31 C30 120.2(4) . .
C32 C31 F9 119.8(5) . .
C27 C32 F10 121.2(4) . .
C31 C32 F10 115.2(4) . .
C31 C32 C27 123.6(4) . .
C33 B3 C27 101.0(3) . .
C21 B3 C27 114.4(3) . .
C21 B3 C33 114.3(3) . .
C39 B3 C27 114.7(3) . .
C39 B3 C33 112.9(3) . .
C39 B3 C21 100.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F13 C36 1.345(4) .
F3 C24 1.347(4) .
F1 C22 1.354(4) .
F4 C25 1.361(4) .
F5 C26 1.355(4) .
F15 C38 1.348(4) .
F14 C37 1.337(4) .
F12 C35 1.344(4) .
F11 C34 1.365(4) .
F18 C42 1.347(4) .
F17 C41 1.348(5) .
F16 C40 1.357(4) .
F19 C43 1.354(4) .
F20 C44 1.349(4) .
F10 C32 1.350(5) .
F7 C29 1.351(5) .
F6 C28 1.356(5) .
F2 C23 1.351(5) .
C19 H19a 0.9900 .
C19 H19b 0.9900 .
C19 C20 1.522(8) .
C19 C18 1.518(9) .
C20 H20a 0.9900 .
C20 H20b 0.9900 .
C20 C13 1.527(7) .
C13 H13 1.0000 .
C13 B2 1.554(6) .
C13 C14 1.560(6) .
B2 N1 1.468(6) .
B2 C17 1.625(7) .
N1 C1 1.372(6) .
N1 C2 1.388(5) .
C1 B1 1.586(6) .
C1 N2 1.335(5) .
B1 C9 1.546(6) .
B1 C5 1.557(6) .
C9 H9 1.0000 .
C9 C10 1.524(6) .
C9 C8 1.556(7) .
C10 H10a 0.9900 .
C10 H10b 0.9900 .
C10 C11 1.540(7) .
C11 H11a 0.9900 .
C11 H11b 0.9900 .
C11 C12 1.500(8) .
C15 H15 0.9500 .
C15 C14 1.458(9) .
C15 C16 1.499(9) .
C14 H14a 0.9900 .
C14 H14b 0.9900 .
C18 H18a 0.9900 .
C18 H18b 0.9900 .
C18 C17 1.550(9) .
C17 H17 1.0000 .
C17 C16 1.522(8) .
C16 H16a 0.9900 .
C16 H16b 0.9900 .
C2 H2 0.9500 .
C2 C3 1.285(7) .
C3 H3 0.9500 .
C3 N2 1.354(6) .
N2 C4 1.440(6) .
C8 H8a 0.9900 .
C8 H8b 0.9900 .
C8 C7 1.500(7) .
C7 H7a 0.9900 .
C7 H7b 0.9900 .
C7 C6 1.561(8) .
C6 H6a 0.9900 .
C6 H6b 0.9900 .
C6 C5 1.540(7) .
C5 H5 1.0000 .
C5 C12 1.548(7) .
C12 H12a 0.9900 .
C12 H12b 0.9900 .
C4 H4a 0.9800 .
C4 H4b 0.9800 .
C4 H4c 0.9800 .
F8 C30 1.346(5) .
C30 C29 1.365(7) .
C30 C31 1.365(8) .
C29 C28 1.384(6) .
C28 C27 1.384(6) .
C27 C32 1.388(6) .
C27 B3 1.654(5) .
C33 C38 1.386(5) .
C33 C34 1.384(5) .
C33 B3 1.652(5) .
C38 C37 1.385(5) .
C37 C36 1.370(6) .
C36 C35 1.373(6) .
C24 C23 1.371(6) .
C24 C25 1.370(6) .
C23 C22 1.379(5) .
C22 C21 1.394(5) .
C21 C26 1.390(5) .
C21 B3 1.652(5) .
C26 C25 1.375(5) .
C35 C34 1.374(5) .
C39 C44 1.393(5) .
C39 C40 1.383(5) .
C39 B3 1.659(5) .
C44 C43 1.382(6) .
C43 C42 1.363(6) .
C42 C41 1.374(6) .
C41 C40 1.382(5) .
C31 F9 1.359(5) .
C31 C32 1.393(6) .
