#------------------------------------------------------------------------------
#$Date: 2021-01-20 01:59:51 +0200 (Wed, 20 Jan 2021) $
#$Revision: 261059 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/55/4135520.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_4135520
loop_
_publ_author_name
'Li, Jun'
'Daniliuc, Constantin G.'
'Kartha, Kalathil K.'
'Fernández, Gustavo'
'Kehr, Gerald'
'Erker, Gerhard'
_publ_section_title
;
 Introducing the Dihydro-1,3-azaboroles: Convenient Entry by a
 Three-Component Reaction, Synthetic and Photophysical Application
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c12236
_journal_year                    2021
_chemical_formula_sum            'C40 H44 B F9 N2'
_chemical_formula_weight         734.58
_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
_audit_creation_method           'APEX3 v2016.1-0'
_cell_angle_alpha                109.702(5)
_cell_angle_beta                 92.143(5)
_cell_angle_gamma                92.957(6)
_cell_formula_units_Z            2
_cell_length_a                   8.6311(7)
_cell_length_b                   14.6478(12)
_cell_length_c                   15.7274(12)
_cell_measurement_reflns_used    3062
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      62.3660
_cell_measurement_theta_min      2.9896
_cell_volume                     1866.3(3)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1013
_diffrn_reflns_av_unetI/netI     0.1040
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29287
_diffrn_reflns_theta_full        66.67
_diffrn_reflns_theta_max         66.67
_diffrn_reflns_theta_min         5.08
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.263
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         6493
_refine_ls_number_restraints     121
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0615
_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)+(0.0317P)²+1.6155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                4026
_reflns_number_total             6493
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c12236_si_004.cif
_cod_data_source_block           erk9578
_cod_database_code               4135520
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.5987(3) 0.6091(2) 0.6645(2) 0.0270(7) Uani d . . . 1.0 . .
H H1 0.580(5) 0.643(3) 0.630(3) 0.050(13) Uiso d . . . 1.0 . .
N N2 0.8574(3) 0.77594(19) 0.90451(19) 0.0264(6) Uani d . . . 1.0 . .
C C1 0.7818(4) 0.6890(2) 0.8976(2) 0.0277(8) Uani d . . . 1.0 . .
C C2 0.6842(4) 0.6369(2) 0.8219(2) 0.0261(7) Uani d . . . 1.0 . .
C C3 0.6781(4) 0.6663(2) 0.7442(2) 0.0247(7) Uani d . . . 1.0 . .
C C4 0.8427(4) 0.8163(2) 0.8380(2) 0.0274(8) Uani d . . . 1.0 . .
H H4 0.8926 0.8784 0.8471 0.033 Uiso calc U . R 1.0 . .
C C11 0.8122(4) 0.6535(3) 0.9749(3) 0.0345(9) Uani d . . . 1.0 . .
H H11 0.7535 0.6851 1.0297 0.041 Uiso calc U . R 1.0 . .
C C12 0.9724(5) 0.6262(3) 0.9944(3) 0.0443(10) Uani d . . . 1.0 . .
H H12A 1.0539 0.6296 0.9527 0.053 Uiso calc U . R 1.0 . .
H H12B 1.0096 0.6432 1.0585 0.053 Uiso calc U . R 1.0 . .
C C13 0.8430(4) 0.5498(3) 0.9593(3) 0.0408(10) Uani d . . . 1.0 . .
H H13A 0.8003 0.5193 1.0016 0.049 Uiso calc U . R 1.0 . .
H H13B 0.8446 0.5057 0.8959 0.049 Uiso calc U . R 1.0 . .
C C21 0.5755(4) 0.5567(2) 0.8284(2) 0.0296(8) Uani d . . . 1.0 . .
H H21 0.6108 0.4894 0.8026 0.036 Uiso calc U . R 1.0 . .
C C22 0.4760(4) 0.5753(3) 0.9082(3) 0.0374(9) Uani d . . . 1.0 . .
H H22A 0.4875 0.6406 0.9553 0.045 Uiso calc U . R 1.0 . .
H H22B 0.4538 0.5211 0.9312 0.045 Uiso calc U . R 1.0 . .
C C23 0.4026(4) 0.5668(3) 0.8171(2) 0.0326(8) Uani d . . . 1.0 . .
H H23A 0.3695 0.6269 0.8084 0.039 Uiso calc U . R 1.0 . .
H H23B 0.3358 0.5073 0.7843 0.039 Uiso calc U . R 1.0 . .
B B1 0.7509(4) 0.7652(3) 0.7526(3) 0.0253(8) Uani d . . . 1.0 . .
C C31 0.7369(4) 0.8226(2) 0.6824(2) 0.0257(7) Uani d . . . 1.0 . .
C C32 0.6140(4) 0.8822(2) 0.6827(2) 0.0259(7) Uani d . . . 1.0 . .
C C33 0.6131(4) 0.9478(2) 0.6362(2) 0.0280(8) Uani d . . . 1.0 . .
H H33 0.5286 0.9878 0.64 0.034 Uiso calc U . R 1.0 . .
C C34 0.7374(4) 0.9544(2) 0.5842(2) 0.0309(8) Uani d . . . 1.0 . .
C C35 0.8584(4) 0.8939(2) 0.5778(2) 0.0313(8) Uani d . . . 1.0 . .
H H35 0.9422 0.8964 0.5409 0.038 Uiso calc U . R 1.0 . .
C C36 0.8560(4) 0.8293(2) 0.6260(2) 0.0284(8) Uani d . . . 1.0 . .
C C37 0.4781(4) 0.8800(2) 0.7392(3) 0.0304(8) Uani d . . . 1.0 . .
F F1 0.4154(2) 0.79011(14) 0.72415(16) 0.0413(6) Uani d . . . 1.0 . .
F F2 0.5160(2) 0.91852(16) 0.82887(14) 0.0417(5) Uani d . . . 1.0 . .
F F3 0.3622(2) 0.93188(14) 0.72367(15) 0.0384(5) Uani d . . . 1.0 . .
C C38 0.7470(5) 1.0284(3) 0.5382(3) 0.0394(9) Uani d . . . 1.0 . .
F F4 0.6191(3) 1.07795(16) 0.54434(17) 0.0515(6) Uani d . . . 1.0 . .
F F5 0.8653(3) 1.09527(16) 0.57426(17) 0.0535(7) Uani d . . . 1.0 . .
F F6 0.7710(3) 0.98969(17) 0.45076(16) 0.0606(7) Uani d . . . 1.0 . .
C C39 0.9917(4) 0.7675(3) 0.6169(3) 0.0328(8) Uani d . . . 1.0 . .
F F7 1.0788(3) 0.76820(18) 0.54853(17) 0.0565(7) Uani d . . . 1.0 . .
F F8 0.9496(2) 0.67425(14) 0.60258(16) 0.0423(6) Uani d . . . 1.0 . .
F F9 1.0887(2) 0.79724(18) 0.69205(17) 0.0510(6) Uani d . . . 1.0 . .
C C41 0.5604(4) 0.5070(2) 0.6305(2) 0.0284(8) Uani d . . . 1.0 . .
C C42 0.6737(4) 0.4404(2) 0.6287(2) 0.0307(8) Uani d . . . 1.0 . .
C C43 0.6288(4) 0.3416(3) 0.5918(3) 0.0358(9) Uani d . . . 1.0 . .
H H43 0.7023 0.2956 0.5919 0.043 Uiso calc U . R 1.0 . .
C C44 0.4799(5) 0.3090(3) 0.5549(3) 0.0393(9) Uani d . . . 1.0 . .
H H44 0.4521 0.2412 0.5299 0.047 Uiso calc U . R 1.0 . .
C C45 0.3714(4) 0.3752(3) 0.5546(2) 0.0354(9) Uani d . . . 1.0 . .
H H45 0.2696 0.3524 0.5285 0.043 Uiso calc U . R 1.0 . .
C C46 0.4090(4) 0.4746(2) 0.5919(2) 0.0311(8) Uani d . . . 1.0 . .
C C47 0.8402(4) 0.4721(3) 0.6607(3) 0.0368(9) Uani d . . . 1.0 . .
H H47A 0.8717 0.5293 0.6448 0.055 Uiso calc U . R 1.0 . .
H H47B 0.9063 0.4192 0.6315 0.055 Uiso calc U . R 1.0 . .
H H47C 0.8515 0.4884 0.7264 0.055 Uiso calc U . R 1.0 . .
C C48 0.2901(4) 0.5459(3) 0.5916(3) 0.0371(9) Uani d . . . 1.0 . .
H H48A 0.1915 0.5105 0.5635 0.056 Uiso calc U . R 1.0 . .
H H48B 0.3264 0.5867 0.5573 0.056 Uiso calc U . R 1.0 . .
H H48C 0.2748 0.5869 0.654 0.056 Uiso calc U . R 1.0 . .
C C51 0.9400(4) 0.8345(2) 0.9895(2) 0.0285(8) Uani d . . . 1.0 . .
C C52 1.1018(4) 0.8422(2) 0.9955(2) 0.0320(8) Uani d . . . 1.0 . .
C C53 1.1742(4) 0.8951(3) 1.0788(3) 0.0378(9) Uani d . . . 1.0 . .
H H53 1.2845 0.9009 1.0857 0.045 Uiso calc U . R 1.0 . .
C C54 1.0887(5) 0.9397(3) 1.1518(3) 0.0412(10) Uani d . . . 1.0 . .
H H54 1.1404 0.9734 1.2091 0.049 Uiso calc U . R 1.0 . .
C C55 0.9297(5) 0.9358(3) 1.1426(3) 0.0374(9) Uani d . . . 1.0 . .
H H55 0.8725 0.9689 1.193 0.045 Uiso calc U . R 1.0 . .
C C56 0.8513(4) 0.8839(2) 1.0602(2) 0.0300(8) Uani d . . . 1.0 . .
C C57 1.1949(4) 0.7957(3) 0.9146(3) 0.0461(10) Uani d . . . 1.0 . .
H H57A 1.1994 0.8371 0.8769 0.069 Uiso calc U . R 1.0 . .
H H57B 1.1451 0.7318 0.8791 0.069 Uiso calc U . R 1.0 . .
H H57C 1.3005 0.7881 0.9351 0.069 Uiso calc U . R 1.0 . .
C C58 0.6764(4) 0.8823(3) 1.0484(3) 0.0454(10) Uani d . . . 1.0 . .
H H58A 0.6484 0.8977 0.994 0.068 Uiso calc U . R 1.0 . .
H H58B 0.6369 0.9307 1.1014 0.068 Uiso calc U . R 1.0 . .
H H58C 0.6306 0.8176 1.0421 0.068 Uiso calc U . R 1.0 . .
C C61 0.8814(18) 0.6985(18) 0.2680(17) 0.075(5) Uani d U P D 0.66(5) A 1
H H61A 0.852 0.6521 0.2981 0.112 Uiso calc U P R 0.66(5) A 1
H H61B 0.9751 0.7381 0.2992 0.112 Uiso calc U P R 0.66(5) A 1
H H61C 0.9022 0.6631 0.2049 0.112 Uiso calc U P R 0.66(5) A 1
C C62 0.7489(19) 0.7645(12) 0.2706(12) 0.062(3) Uani d U P D 0.66(5) A 1
H H62A 0.7292 0.8001 0.3345 0.075 Uiso calc U P R 0.66(5) A 1
H H62B 0.7815 0.813 0.2425 0.075 Uiso calc U P R 0.66(5) A 1
C C63 0.5995(17) 0.7101(12) 0.222(2) 0.047(3) Uani d U P D 0.66(5) A 1
H H63A 0.5687 0.661 0.2501 0.056 Uiso calc U P R 0.66(5) A 1
H H63B 0.6201 0.6748 0.1585 0.056 Uiso calc U P R 0.66(5) A 1
C C64 0.4640(19) 0.7724(8) 0.2239(11) 0.047(3) Uani d U P D 0.66(5) A 1
H H64A 0.4919 0.8189 0.1928 0.057 Uiso calc U P R 0.66(5) A 1
H H64B 0.4467 0.8105 0.2876 0.057 Uiso calc U P R 0.66(5) A 1
C C65 0.3133(17) 0.7154(13) 0.1796(14) 0.049(3) Uani d U P D 0.66(5) A 1
H H65A 0.3301 0.6749 0.1173 0.073 Uiso calc U P R 0.66(5) A 1
H H65B 0.2337 0.7606 0.1792 0.073 Uiso calc U P R 0.66(5) A 1
H H65C 0.2786 0.6738 0.2137 0.073 Uiso calc U P R 0.66(5) A 1
C C61A 0.897(4) 0.675(2) 0.259(3) 0.055(6) Uani d U P D 0.34(5) A 2
H H61D 0.8613 0.6398 0.2993 0.083 Uiso calc U P R 0.34(5) A 2
H H61E 0.9999 0.7074 0.2824 0.083 Uiso calc U P R 0.34(5) A 2
H H61F 0.9047 0.6281 0.1983 0.083 Uiso calc U P R 0.34(5) A 2
C C62A 0.784(3) 0.7490(17) 0.2570(19) 0.045(5) Uani d U P D 0.34(5) A 2
H H62C 0.7816 0.7978 0.3184 0.054 Uiso calc U P R 0.34(5) A 2
H H62D 0.8204 0.7833 0.2162 0.054 Uiso calc U P R 0.34(5) A 2
C C63A 0.620(3) 0.705(2) 0.225(4) 0.038(5) Uani d U P D 0.34(5) A 2
H H63C 0.5905 0.6601 0.2574 0.046 Uiso calc U P R 0.34(5) A 2
H H63D 0.6168 0.6678 0.1598 0.046 Uiso calc U P R 0.34(5) A 2
C C64A 0.502(3) 0.7826(19) 0.242(2) 0.052(5) Uani d U P D 0.34(5) A 2
H H64C 0.54 0.8335 0.218 0.062 Uiso calc U P R 0.34(5) A 2
H H64D 0.4938 0.8135 0.3081 0.062 Uiso calc U P R 0.34(5) A 2
C C65A 0.343(3) 0.740(3) 0.198(2) 0.047(6) Uani d U P D 0.34(5) A 2
H H65D 0.3448 0.7244 0.132 0.071 Uiso calc U P R 0.34(5) A 2
H H65E 0.2655 0.788 0.2212 0.071 Uiso calc U P R 0.34(5) A 2
H H65F 0.3144 0.6812 0.2113 0.071 Uiso calc U P R 0.34(5) A 2
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 C41 . . 130.2(3) ?
C3 N1 H1 . . 110.(3) ?
C41 N1 H1 . . 119.(3) ?
C4 N2 C1 . . 122.2(3) ?
C4 N2 C51 . . 117.7(3) ?
C1 N2 C51 . . 119.6(3) ?
N2 C1 C2 . . 121.3(3) ?
N2 C1 C11 . . 115.9(3) ?
C2 C1 C11 . . 122.8(3) ?
C1 C2 C3 . . 120.3(3) ?
C1 C2 C21 . . 118.2(3) ?
C3 C2 C21 . . 121.1(3) ?
N1 C3 C2 . . 121.3(3) ?
N1 C3 B1 . . 120.1(3) ?
C2 C3 B1 . . 118.5(3) ?
N2 C4 B1 . . 121.4(3) ?
N2 C4 H4 . . 119.3 ?
B1 C4 H4 . . 119.3 ?
C13 C11 C1 . . 121.2(3) ?
C13 C11 C12 . . 59.4(2) ?
C1 C11 C12 . . 120.3(3) ?
C13 C11 H11 . . 114.9 ?
C1 C11 H11 . . 114.9 ?
C12 C11 H11 . . 114.9 ?
C13 C12 C11 . . 59.8(2) ?
C13 C12 H12A . . 117.8 ?
C11 C12 H12A . . 117.8 ?
C13 C12 H12B . . 117.8 ?
C11 C12 H12B . . 117.8 ?
H12A C12 H12B . . 114.9 ?
C12 C13 C11 . . 60.8(2) ?
C12 C13 H13A . . 117.7 ?
C11 C13 H13A . . 117.7 ?
C12 C13 H13B . . 117.7 ?
C11 C13 H13B . . 117.7 ?
H13A C13 H13B . . 114.8 ?
C2 C21 C22 . . 119.5(3) ?
C2 C21 C23 . . 117.5(3) ?
C22 C21 C23 . . 59.9(2) ?
C2 C21 H21 . . 116.1 ?
C22 C21 H21 . . 116.1 ?
C23 C21 H21 . . 116.1 ?
C21 C22 C23 . . 60.5(2) ?
C21 C22 H22A . . 117.7 ?
C23 C22 H22A . . 117.7 ?
C21 C22 H22B . . 117.7 ?
C23 C22 H22B . . 117.7 ?
H22A C22 H22B . . 114.8 ?
C22 C23 C21 . . 59.6(2) ?
C22 C23 H23A . . 117.8 ?
C21 C23 H23A . . 117.8 ?
C22 C23 H23B . . 117.8 ?
C21 C23 H23B . . 117.8 ?
H23A C23 H23B . . 114.9 ?
C4 B1 C3 . . 115.2(3) ?
C4 B1 C31 . . 116.3(3) ?
C3 B1 C31 . . 128.5(3) ?
C36 C31 C32 . . 114.6(3) ?
C36 C31 B1 . . 122.9(3) ?
C32 C31 B1 . . 121.9(3) ?
C33 C32 C31 . . 123.6(3) ?
C33 C32 C37 . . 116.8(3) ?
C31 C32 C37 . . 119.5(3) ?
C32 C33 C34 . . 119.3(3) ?
C32 C33 H33 . . 120.3 ?
C34 C33 H33 . . 120.3 ?
C35 C34 C33 . . 119.7(3) ?
C35 C34 C38 . . 119.0(3) ?
C33 C34 C38 . . 121.3(3) ?
C34 C35 C36 . . 119.4(3) ?
C34 C35 H35 . . 120.3 ?
C36 C35 H35 . . 120.3 ?
C35 C36 C31 . . 123.2(3) ?
C35 C36 C39 . . 116.4(3) ?
C31 C36 C39 . . 120.3(3) ?
F1 C37 F3 . . 106.4(3) ?
F1 C37 F2 . . 106.5(3) ?
F3 C37 F2 . . 105.4(3) ?
F1 C37 C32 . . 113.0(3) ?
F3 C37 C32 . . 112.2(3) ?
F2 C37 C32 . . 112.7(3) ?
F6 C38 F4 . . 106.8(3) ?
F6 C38 F5 . . 106.1(3) ?
F4 C38 F5 . . 106.0(3) ?
F6 C38 C34 . . 112.6(3) ?
F4 C38 C34 . . 113.4(3) ?
F5 C38 C34 . . 111.5(3) ?
F8 C39 F7 . . 106.1(3) ?
F8 C39 F9 . . 106.0(3) ?
F7 C39 F9 . . 106.0(3) ?
F8 C39 C36 . . 113.0(3) ?
F7 C39 C36 . . 113.0(3) ?
F9 C39 C36 . . 112.1(3) ?
C46 C41 C42 . . 121.0(3) ?
C46 C41 N1 . . 117.7(3) ?
C42 C41 N1 . . 121.1(3) ?
C43 C42 C41 . . 117.8(3) ?
C43 C42 C47 . . 119.5(3) ?
C41 C42 C47 . . 122.6(3) ?
C44 C43 C42 . . 121.6(3) ?
C44 C43 H43 . . 119.2 ?
C42 C43 H43 . . 119.2 ?
C43 C44 C45 . . 119.8(3) ?
C43 C44 H44 . . 120.1 ?
C45 C44 H44 . . 120.1 ?
C44 C45 C46 . . 121.0(4) ?
C44 C45 H45 . . 119.5 ?
C46 C45 H45 . . 119.5 ?
C45 C46 C41 . . 118.6(3) ?
C45 C46 C48 . . 120.6(3) ?
C41 C46 C48 . . 120.8(3) ?
C42 C47 H47A . . 109.5 ?
C42 C47 H47B . . 109.5 ?
H47A C47 H47B . . 109.5 ?
C42 C47 H47C . . 109.5 ?
H47A C47 H47C . . 109.5 ?
H47B C47 H47C . . 109.5 ?
C46 C48 H48A . . 109.5 ?
C46 C48 H48B . . 109.5 ?
H48A C48 H48B . . 109.5 ?
C46 C48 H48C . . 109.5 ?
H48A C48 H48C . . 109.5 ?
H48B C48 H48C . . 109.5 ?
C56 C51 C52 . . 123.0(3) ?
C56 C51 N2 . . 117.4(3) ?
C52 C51 N2 . . 119.6(3) ?
C53 C52 C51 . . 117.2(3) ?
C53 C52 C57 . . 121.2(3) ?
C51 C52 C57 . . 121.6(3) ?
C54 C53 C52 . . 120.9(4) ?
C54 C53 H53 . . 119.5 ?
C52 C53 H53 . . 119.5 ?
C55 C54 C53 . . 120.6(4) ?
C55 C54 H54 . . 119.7 ?
C53 C54 H54 . . 119.7 ?
C54 C55 C56 . . 120.7(4) ?
C54 C55 H55 . . 119.7 ?
C56 C55 H55 . . 119.7 ?
C51 C56 C55 . . 117.4(3) ?
C51 C56 C58 . . 121.6(3) ?
C55 C56 C58 . . 121.0(3) ?
C52 C57 H57A . . 109.5 ?
C52 C57 H57B . . 109.5 ?
H57A C57 H57B . . 109.5 ?
C52 C57 H57C . . 109.5 ?
H57A C57 H57C . . 109.5 ?
H57B C57 H57C . . 109.5 ?
C56 C58 H58A . . 109.5 ?
C56 C58 H58B . . 109.5 ?
H58A C58 H58B . . 109.5 ?
C56 C58 H58C . . 109.5 ?
H58A C58 H58C . . 109.5 ?
H58B C58 H58C . . 109.5 ?
C62 C61 H61A . . 109.5 ?
C62 C61 H61B . . 109.5 ?
H61A C61 H61B . . 109.5 ?
C62 C61 H61C . . 109.5 ?
H61A C61 H61C . . 109.5 ?
H61B C61 H61C . . 109.5 ?
C63 C62 C61 . . 113.5(10) ?
C63 C62 H62A . . 108.9 ?
C61 C62 H62A . . 108.9 ?
C63 C62 H62B . . 108.9 ?
C61 C62 H62B . . 108.9 ?
H62A C62 H62B . . 107.7 ?
C62 C63 C64 . . 115.5(10) ?
C62 C63 H63A . . 108.4 ?
C64 C63 H63A . . 108.4 ?
C62 C63 H63B . . 108.4 ?
C64 C63 H63B . . 108.4 ?
H63A C63 H63B . . 107.5 ?
C63 C64 C65 . . 114.3(8) ?
C63 C64 H64A . . 108.7 ?
C65 C64 H64A . . 108.7 ?
C63 C64 H64B . . 108.7 ?
C65 C64 H64B . . 108.7 ?
H64A C64 H64B . . 107.6 ?
C64 C65 H65A . . 109.5 ?
C64 C65 H65B . . 109.5 ?
H65A C65 H65B . . 109.5 ?
C64 C65 H65C . . 109.5 ?
H65A C65 H65C . . 109.5 ?
H65B C65 H65C . . 109.5 ?
C62A C61A H61D . . 109.5 ?
C62A C61A H61E . . 109.5 ?
H61D C61A H61E . . 109.5 ?
C62A C61A H61F . . 109.5 ?
H61D C61A H61F . . 109.5 ?
H61E C61A H61F . . 109.5 ?
C63A C62A C61A . . 113.5(18) ?
C63A C62A H62C . . 108.9 ?
C61A C62A H62C . . 108.9 ?
C63A C62A H62D . . 108.9 ?
C61A C62A H62D . . 108.9 ?
H62C C62A H62D . . 107.7 ?
C62A C63A C64A . . 112.2(17) ?
C62A C63A H63C . . 109.2 ?
C64A C63A H63C . . 109.2 ?
C62A C63A H63D . . 109.2 ?
C64A C63A H63D . . 109.2 ?
H63C C63A H63D . . 107.9 ?
C63A C64A C65A . . 112.1(16) ?
C63A C64A H64C . . 109.2 ?
C65A C64A H64C . . 109.2 ?
C63A C64A H64D . . 109.2 ?
C65A C64A H64D . . 109.2 ?
H64C C64A H64D . . 107.9 ?
C64A C65A H65D . . 109.5 ?
C64A C65A H65E . . 109.5 ?
H65D C65A H65E . . 109.5 ?
C64A C65A H65F . . 109.5 ?
H65D C65A H65F . . 109.5 ?
H65E C65A H65F . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C3 . 1.383(4) ?
N1 C41 . 1.424(4) ?
N1 H1 . 0.87(4) ?
N2 C4 . 1.369(4) ?
N2 C1 . 1.370(4) ?
N2 C51 . 1.457(4) ?
C1 C2 . 1.399(5) ?
C1 C11 . 1.494(5) ?
C2 C3 . 1.426(4) ?
C2 C21 . 1.500(5) ?
C3 B1 . 1.511(5) ?
C4 B1 . 1.474(5) ?
C4 H4 . 0.95 ?
C11 C13 . 1.494(5) ?
C11 C12 . 1.508(5) ?
C11 H11 . 1.0 ?
C12 C13 . 1.488(5) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C21 C22 . 1.504(5) ?
C21 C23 . 1.517(5) ?
C21 H21 . 1.0 ?
C22 C23 . 1.508(5) ?
C22 H22A . 0.99 ?
C22 H22B . 0.99 ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
B1 C31 . 1.601(5) ?
C31 C36 . 1.404(5) ?
C31 C32 . 1.408(5) ?
C32 C33 . 1.389(4) ?
C32 C37 . 1.503(5) ?
C33 C34 . 1.391(5) ?
C33 H33 . 0.95 ?
C34 C35 . 1.389(5) ?
C34 C38 . 1.493(5) ?
C35 C36 . 1.398(5) ?
C35 H35 . 0.95 ?
C36 C39 . 1.499(5) ?
C37 F1 . 1.338(4) ?
C37 F3 . 1.350(4) ?
C37 F2 . 1.351(4) ?
C38 F6 . 1.329(4) ?
C38 F4 . 1.341(4) ?
C38 F5 . 1.342(5) ?
C39 F8 . 1.335(4) ?
C39 F7 . 1.337(4) ?
C39 F9 . 1.353(4) ?
C41 C46 . 1.409(5) ?
C41 C42 . 1.411(5) ?
C42 C43 . 1.393(5) ?
C42 C47 . 1.501(5) ?
C43 C44 . 1.382(6) ?
C43 H43 . 0.95 ?
C44 C45 . 1.384(5) ?
C44 H44 . 0.95 ?
C45 C46 . 1.389(5) ?
C45 H45 . 0.95 ?
C46 C48 . 1.502(5) ?
C47 H47A . 0.98 ?
C47 H47B . 0.98 ?
C47 H47C . 0.98 ?
C48 H48A . 0.98 ?
C48 H48B . 0.98 ?
C48 H48C . 0.98 ?
C51 C56 . 1.386(5) ?
C51 C52 . 1.393(5) ?
C52 C53 . 1.382(5) ?
C52 C57 . 1.509(5) ?
C53 C54 . 1.378(6) ?
C53 H53 . 0.95 ?
C54 C55 . 1.371(6) ?
C54 H54 . 0.95 ?
C55 C56 . 1.390(5) ?
C55 H55 . 0.95 ?
C56 C58 . 1.512(5) ?
C57 H57A . 0.98 ?
C57 H57B . 0.98 ?
C57 H57C . 0.98 ?
C58 H58A . 0.98 ?
C58 H58B . 0.98 ?
C58 H58C . 0.98 ?
C61 C62 . 1.528(10) ?
C61 H61A . 0.98 ?
C61 H61B . 0.98 ?
C61 H61C . 0.98 ?
C62 C63 . 1.512(10) ?
C62 H62A . 0.99 ?
C62 H62B . 0.99 ?
C63 C64 . 1.516(10) ?
C63 H63A . 0.99 ?
C63 H63B . 0.99 ?
C64 C65 . 1.517(10) ?
C64 H64A . 0.99 ?
C64 H64B . 0.99 ?
C65 H65A . 0.98 ?
C65 H65B . 0.98 ?
C65 H65C . 0.98 ?
C61A C62A . 1.515(14) ?
C61A H61D . 0.98 ?
C61A H61E . 0.98 ?
C61A H61F . 0.98 ?
C62A C63A . 1.514(14) ?
C62A H62C . 0.99 ?
C62A H62D . 0.99 ?
C63A C64A . 1.519(14) ?
C63A H63C . 0.99 ?
C63A H63D . 0.99 ?
C64A C65A . 1.525(14) ?
C64A H64C . 0.99 ?
C64A H64D . 0.99 ?
C65A H65D . 0.98 ?
C65A H65E . 0.98 ?
C65A H65F . 0.98 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N2 C1 C2 . . . . -0.4(5) ?
C51 N2 C1 C2 . . . . 171.3(3) ?
C4 N2 C1 C11 . . . . 178.8(3) ?
C51 N2 C1 C11 . . . . -9.5(4) ?
N2 C1 C2 C3 . . . . 8.9(5) ?
C11 C1 C2 C3 . . . . -170.2(3) ?
N2 C1 C2 C21 . . . . -164.9(3) ?
C11 C1 C2 C21 . . . . 15.9(5) ?
C41 N1 C3 C2 . . . . -24.7(5) ?
C41 N1 C3 B1 . . . . 159.7(3) ?
C1 C2 C3 N1 . . . . 171.4(3) ?
C21 C2 C3 N1 . . . . -15.0(5) ?
C1 C2 C3 B1 . . . . -13.0(4) ?
C21 C2 C3 B1 . . . . 160.7(3) ?
C1 N2 C4 B1 . . . . -3.5(5) ?
C51 N2 C4 B1 . . . . -175.3(3) ?
N2 C1 C11 C13 . . . . -135.6(3) ?
C2 C1 C11 C13 . . . . 43.6(5) ?
N2 C1 C11 C12 . . . . -65.2(4) ?
C2 C1 C11 C12 . . . . 114.0(4) ?
C1 C11 C12 C13 . . . . -110.6(4) ?
C1 C11 C13 C12 . . . . 109.1(4) ?
C1 C2 C21 C22 . . . . 49.0(4) ?
C3 C2 C21 C22 . . . . -124.8(4) ?
C1 C2 C21 C23 . . . . 118.1(4) ?
C3 C2 C21 C23 . . . . -55.7(4) ?
C2 C21 C22 C23 . . . . 106.5(3) ?
C2 C21 C23 C22 . . . . -109.9(4) ?
N2 C4 B1 C3 . . . . -0.8(5) ?
N2 C4 B1 C31 . . . . 177.3(3) ?
N1 C3 B1 C4 . . . . -175.5(3) ?
C2 C3 B1 C4 . . . . 8.8(4) ?
N1 C3 B1 C31 . . . . 6.6(5) ?
C2 C3 B1 C31 . . . . -169.1(3) ?
C4 B1 C31 C36 . . . . 78.8(4) ?
C3 B1 C31 C36 . . . . -103.3(4) ?
C4 B1 C31 C32 . . . . -91.3(4) ?
C3 B1 C31 C32 . . . . 86.6(5) ?
C36 C31 C32 C33 . . . . -4.2(5) ?
B1 C31 C32 C33 . . . . 166.6(3) ?
C36 C31 C32 C37 . . . . 178.9(3) ?
B1 C31 C32 C37 . . . . -10.3(5) ?
C31 C32 C33 C34 . . . . 1.8(5) ?
C37 C32 C33 C34 . . . . 178.8(3) ?
C32 C33 C34 C35 . . . . 1.4(5) ?
C32 C33 C34 C38 . . . . -175.7(3) ?
C33 C34 C35 C36 . . . . -1.9(5) ?
C38 C34 C35 C36 . . . . 175.3(3) ?
C34 C35 C36 C31 . . . . -0.8(6) ?
C34 C35 C36 C39 . . . . -179.1(3) ?
C32 C31 C36 C35 . . . . 3.7(5) ?
B1 C31 C36 C35 . . . . -167.1(3) ?
C32 C31 C36 C39 . . . . -178.1(3) ?
B1 C31 C36 C39 . . . . 11.2(5) ?
C33 C32 C37 F1 . . . . 130.8(3) ?
C31 C32 C37 F1 . . . . -52.1(4) ?
C33 C32 C37 F3 . . . . 10.4(4) ?
C31 C32 C37 F3 . . . . -172.4(3) ?
C33 C32 C37 F2 . . . . -108.4(3) ?
C31 C32 C37 F2 . . . . 68.7(4) ?
C35 C34 C38 F6 . . . . 54.5(5) ?
C33 C34 C38 F6 . . . . -128.3(4) ?
C35 C34 C38 F4 . . . . 175.9(3) ?
C33 C34 C38 F4 . . . . -6.9(5) ?
C35 C34 C38 F5 . . . . -64.6(4) ?
C33 C34 C38 F5 . . . . 112.6(4) ?
C35 C36 C39 F8 . . . . -134.2(3) ?
C31 C36 C39 F8 . . . . 47.4(5) ?
C35 C36 C39 F7 . . . . -13.7(5) ?
C31 C36 C39 F7 . . . . 167.9(3) ?
C35 C36 C39 F9 . . . . 106.0(4) ?
C31 C36 C39 F9 . . . . -72.3(4) ?
C3 N1 C41 C46 . . . . 136.1(4) ?
C3 N1 C41 C42 . . . . -49.2(5) ?
C46 C41 C42 C43 . . . . -3.3(5) ?
N1 C41 C42 C43 . . . . -177.9(3) ?
C46 C41 C42 C47 . . . . 173.7(3) ?
N1 C41 C42 C47 . . . . -0.9(5) ?
C41 C42 C43 C44 . . . . 2.3(5) ?
C47 C42 C43 C44 . . . . -174.8(3) ?
C42 C43 C44 C45 . . . . -0.3(6) ?
C43 C44 C45 C46 . . . . -0.8(6) ?
C44 C45 C46 C41 . . . . -0.2(5) ?
C44 C45 C46 C48 . . . . -179.7(3) ?
C42 C41 C46 C45 . . . . 2.3(5) ?
N1 C41 C46 C45 . . . . 177.1(3) ?
C42 C41 C46 C48 . . . . -178.2(3) ?
N1 C41 C46 C48 . . . . -3.5(5) ?
C4 N2 C51 C56 . . . . 97.5(4) ?
C1 N2 C51 C56 . . . . -74.5(4) ?
C4 N2 C51 C52 . . . . -79.7(4) ?
C1 N2 C51 C52 . . . . 108.2(4) ?
C56 C51 C52 C53 . . . . 5.7(5) ?
N2 C51 C52 C53 . . . . -177.3(3) ?
C56 C51 C52 C57 . . . . -173.6(3) ?
N2 C51 C52 C57 . . . . 3.4(5) ?
C51 C52 C53 C54 . . . . -1.2(5) ?
C57 C52 C53 C54 . . . . 178.1(3) ?
C52 C53 C54 C55 . . . . -2.7(5) ?
C53 C54 C55 C56 . . . . 2.4(5) ?
C52 C51 C56 C55 . . . . -6.0(5) ?
N2 C51 C56 C55 . . . . 176.9(3) ?
C52 C51 C56 C58 . . . . 173.5(3) ?
N2 C51 C56 C58 . . . . -3.6(5) ?
C54 C55 C56 C51 . . . . 1.9(5) ?
C54 C55 C56 C58 . . . . -177.6(3) ?
C61 C62 C63 C64 . . . . 179.(2) ?
C62 C63 C64 C65 . . . . -177.(2) ?
C61A C62A C63A C64A . . . . 168.(4) ?
C62A C63A C64A C65A . . . . 171.(4) ?
