#------------------------------------------------------------------------------
#$Date: 2021-01-20 01:59:51 +0200 (Wed, 20 Jan 2021) $
#$Revision: 261059 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/55/4135525.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_4135525
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            'C38 H34 B Br F9 N2'
_chemical_formula_weight         780.39
_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   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_cell_angle_alpha                102.7230(10)
_cell_angle_beta                 103.3830(10)
_cell_angle_gamma                91.8600(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7867(2)
_cell_length_b                   12.7686(2)
_cell_length_c                   16.8144(3)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.6922
_cell_measurement_theta_min      3.5625
_cell_volume                     1783.25(6)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0339
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29496
_diffrn_reflns_theta_full        66.84
_diffrn_reflns_theta_max         66.84
_diffrn_reflns_theta_min         3.56
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.255
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.74
_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            yellow
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             794
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.656
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         6271
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0417P)²+1.5839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                5782
_reflns_number_total             6271
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c12236_si_004.cif
_cod_data_source_block           erk9730
_cod_database_code               4135525
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
B B1 0.6688(2) 0.30547(17) 0.74585(14) 0.0138(4) Uani d . . . 1.0 . .
N N1 0.52201(19) 0.16047(13) 0.61923(10) 0.0152(3) Uani d . . . 1.0 . .
H H1 0.583(3) 0.115(2) 0.6395(16) 0.022(6) Uiso d . . . 1.0 . .
N N2 0.56185(18) 0.48517(12) 0.75230(10) 0.0135(3) Uani d . . . 1.0 . .
Br Br1 -0.03289(2) 0.73976(2) 0.53571(2) 0.01983(8) Uani d . . . 1.0 . .
C C1 0.4454(2) 0.44584(15) 0.68156(12) 0.0131(4) Uani d . . . 1.0 . .
C C2 0.4356(2) 0.33811(15) 0.63980(12) 0.0136(4) Uani d . . . 1.0 . .
H H2 0.3531 0.3128 0.5906 0.016 Uiso calc U . R 1.0 . .
C C3 0.5396(2) 0.26470(15) 0.66572(12) 0.0137(4) Uani d . . . 1.0 . .
C C4 0.6705(2) 0.42008(15) 0.78471(12) 0.0143(4) Uani d . . . 1.0 . .
H H4 0.7496 0.451 0.8343 0.017 Uiso calc U . R 1.0 . .
C C11 0.3299(2) 0.51726(15) 0.64809(12) 0.0138(4) Uani d . . . 1.0 . .
C C12 0.2527(2) 0.58748(16) 0.69890(13) 0.0177(4) Uani d . . . 1.0 . .
H H12 0.2747 0.5903 0.7574 0.021 Uiso calc U . R 1.0 . .
C C13 0.1451(2) 0.65282(16) 0.66554(13) 0.0192(4) Uani d . . . 1.0 . .
H H13 0.0953 0.7012 0.7009 0.023 Uiso calc U . R 1.0 . .
C C14 0.1111(2) 0.64676(15) 0.58008(13) 0.0161(4) Uani d . . . 1.0 . .
C C15 0.1805(2) 0.57606(15) 0.52717(13) 0.0165(4) Uani d . . . 1.0 . .
H H15 0.1536 0.5711 0.4683 0.02 Uiso calc U . R 1.0 . .
C C16 0.2904(2) 0.51249(15) 0.56179(12) 0.0147(4) Uani d . . . 1.0 . .
H H16 0.3399 0.4646 0.526 0.018 Uiso calc U . R 1.0 . .
C C31 0.7970(2) 0.23190(15) 0.78458(12) 0.0138(4) Uani d . . . 1.0 . .
C C32 0.9487(2) 0.23027(15) 0.76939(12) 0.0142(4) Uani d . . . 1.0 . .
C C33 1.0594(2) 0.16482(16) 0.80092(12) 0.0162(4) Uani d . . . 1.0 . .
H H33 1.1606 0.167 0.79 0.019 Uiso calc U . R 1.0 . .
C C34 1.0213(2) 0.09629(15) 0.84839(12) 0.0161(4) Uani d . . . 1.0 . .
C C35 0.8754(2) 0.09689(15) 0.86682(12) 0.0164(4) Uani d . . . 1.0 . .
H H35 0.8494 0.0512 0.9002 0.02 Uiso calc U . R 1.0 . .
C C36 0.7677(2) 0.16425(15) 0.83637(12) 0.0139(4) Uani d . . . 1.0 . .
C C37 0.9959(2) 0.30148(17) 0.71676(13) 0.0192(4) Uani d . . . 1.0 . .
F F1 0.88899(14) 0.29366(11) 0.64431(8) 0.0267(3) Uani d . . . 1.0 . .
F F2 1.01725(16) 0.40609(10) 0.75690(9) 0.0311(3) Uani d . . . 1.0 . .
F F3 1.13127(15) 0.27664(12) 0.69654(9) 0.0328(3) Uani d . . . 1.0 . .
C C38 1.1349(2) 0.01903(18) 0.87648(14) 0.0237(5) Uani d . . D 1.0 . .
F F4 1.2825(9) 0.0578(10) 0.8962(10) 0.053(2) Uani d U P D 0.61(5) A 1
F F5 1.1092(14) -0.0100(10) 0.9443(6) 0.0354(17) Uani d U P D 0.61(5) A 1
F F6 1.118(2) -0.0711(8) 0.8170(7) 0.057(2) Uani d U P D 0.61(5) A 1
F F4A 1.2787(14) 0.0685(12) 0.9121(10) 0.037(3) Uani d U P D 0.39(5) A 2
F F5A 1.099(2) -0.032(2) 0.9302(15) 0.054(4) Uani d U P D 0.39(5) A 2
F F6A 1.156(3) -0.0567(19) 0.8123(10) 0.064(4) Uani d U P D 0.39(5) A 2
C C39 0.6140(2) 0.16518(17) 0.86244(13) 0.0187(4) Uani d . . . 1.0 . .
F F7 0.60710(15) 0.09986(11) 0.91386(8) 0.0287(3) Uani d . . . 1.0 . .
F F8 0.48934(14) 0.13581(13) 0.79709(8) 0.0359(3) Uani d . . . 1.0 . .
F F9 0.59133(16) 0.26332(11) 0.90460(9) 0.0339(3) Uani d . . . 1.0 . .
C C41 0.4119(2) 0.11700(15) 0.54061(12) 0.0145(4) Uani d . . . 1.0 . .
C C42 0.4337(2) 0.14465(15) 0.46757(13) 0.0163(4) Uani d . . . 1.0 . .
C C43 0.3286(2) 0.09631(16) 0.39122(13) 0.0193(4) Uani d . . . 1.0 . .
H H43 0.3414 0.114 0.341 0.023 Uiso calc U . R 1.0 . .
C C44 0.2057(2) 0.02294(16) 0.38729(13) 0.0208(4) Uani d . . . 1.0 . .
H H44 0.1348 -0.0088 0.3348 0.025 Uiso calc U . R 1.0 . .
C C45 0.1863(2) -0.00417(16) 0.46013(14) 0.0201(4) Uani d . . . 1.0 . .
H H45 0.1027 -0.0552 0.457 0.024 Uiso calc U . R 1.0 . .
C C46 0.2882(2) 0.04273(15) 0.53778(13) 0.0166(4) Uani d . . . 1.0 . .
C C47 0.5672(2) 0.22339(16) 0.47034(13) 0.0206(4) Uani d . . . 1.0 . .
H H47A 0.5724 0.2241 0.4129 0.031 Uiso calc U . R 1.0 . .
H H47B 0.6661 0.2017 0.5003 0.031 Uiso calc U . R 1.0 . .
H H47C 0.55 0.2956 0.4997 0.031 Uiso calc U . R 1.0 . .
C C48 0.2660(2) 0.01483(17) 0.61720(14) 0.0224(4) Uani d . . . 1.0 . .
H H48A 0.1714 -0.0348 0.604 0.034 Uiso calc U . R 1.0 . .
H H48B 0.2546 0.0807 0.6574 0.034 Uiso calc U . R 1.0 . .
H H48C 0.3576 -0.0195 0.6419 0.034 Uiso calc U . R 1.0 . .
C C51 0.5877(2) 0.59899(15) 0.79397(12) 0.0148(4) Uani d . . . 1.0 . .
C C52 0.6656(2) 0.66822(16) 0.75981(13) 0.0185(4) Uani d . . . 1.0 . .
C C53 0.6962(3) 0.77606(18) 0.80349(14) 0.0276(5) Uani d . . . 1.0 . .
H H53 0.7502 0.8253 0.7824 0.033 Uiso calc U . R 1.0 . .
C C54 0.6490(3) 0.81227(18) 0.87705(15) 0.0334(6) Uani d . . . 1.0 . .
H H54 0.6686 0.8863 0.9052 0.04 Uiso calc U . R 1.0 . .
C C55 0.5736(3) 0.74162(18) 0.90985(14) 0.0292(5) Uani d . . . 1.0 . .
H H55 0.5421 0.7675 0.9605 0.035 Uiso calc U . R 1.0 . .
C C56 0.5433(2) 0.63279(16) 0.86941(13) 0.0202(4) Uani d . . . 1.0 . .
C C57 0.7179(3) 0.62740(18) 0.68001(14) 0.0242(5) Uani d . . . 1.0 . .
H H57A 0.7827 0.5673 0.6863 0.036 Uiso calc U . R 1.0 . .
H H57B 0.7794 0.6857 0.669 0.036 Uiso calc U . R 1.0 . .
H H57C 0.6256 0.6027 0.6329 0.036 Uiso calc U . R 1.0 . .
C C58 0.4666(3) 0.55459(18) 0.90640(14) 0.0269(5) Uani d . . . 1.0 . .
H H58A 0.5447 0.5087 0.9288 0.04 Uiso calc U . R 1.0 . .
H H58B 0.3816 0.5096 0.8626 0.04 Uiso calc U . R 1.0 . .
H H58C 0.4236 0.5945 0.9518 0.04 Uiso calc U . R 1.0 . .
C C61 0.9299(7) 0.3157(5) 0.0834(4) 0.128(2) Uani d . . . 1.0 . .
H H61A 0.9531 0.3609 0.1408 0.193 Uiso calc U . R 1.0 . .
H H61B 0.9669 0.2444 0.0849 0.193 Uiso calc U . R 1.0 . .
H H61C 0.8163 0.3081 0.0591 0.193 Uiso calc U . R 1.0 . .
C C62 1.0065(4) 0.3639(2) 0.03407(18) 0.0460(7) Uani d . . . 1.0 . .
H H62A 0.99 0.3143 -0.022 0.055 Uiso calc U . R 1.0 . .
H H62B 1.1207 0.373 0.0604 0.055 Uiso calc U . R 1.0 . .
C C63 0.9528(3) 0.4726(2) 0.02248(16) 0.0388(6) Uani d . . . 1.0 . .
H H63A 0.8415 0.4624 -0.0095 0.047 Uiso calc U . R 1.0 . .
H H63B 0.9586 0.5201 0.0784 0.047 Uiso calc U . R 1.0 . .
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'
Br Br -0.6763 1.2805 '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
C4 B1 C3 . . 114.37(18) ?
C4 B1 C31 . . 121.67(17) ?
C3 B1 C31 . . 123.94(17) ?
C3 N1 C41 . . 126.74(17) ?
C3 N1 H1 . . 117.3(16) ?
C41 N1 H1 . . 115.9(16) ?
C1 N2 C4 . . 121.58(16) ?
C1 N2 C51 . . 122.30(16) ?
C4 N2 C51 . . 115.92(15) ?
N2 C1 C2 . . 119.75(17) ?
N2 C1 C11 . . 120.58(16) ?
C2 C1 C11 . . 119.66(17) ?
C1 C2 C3 . . 124.00(17) ?
C1 C2 H2 . . 118.0 ?
C3 C2 H2 . . 118.0 ?
N1 C3 C2 . . 119.62(17) ?
N1 C3 B1 . . 122.84(17) ?
C2 C3 B1 . . 117.53(17) ?
N2 C4 B1 . . 122.72(17) ?
N2 C4 H4 . . 118.6 ?
B1 C4 H4 . . 118.6 ?
C16 C11 C12 . . 117.68(18) ?
C16 C11 C1 . . 119.45(17) ?
C12 C11 C1 . . 122.82(17) ?
C13 C12 C11 . . 121.34(19) ?
C13 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C14 C13 C12 . . 119.09(18) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
C13 C14 C15 . . 121.53(18) ?
C13 C14 Br1 . . 118.55(15) ?
C15 C14 Br1 . . 119.91(15) ?
C14 C15 C16 . . 118.67(18) ?
C14 C15 H15 . . 120.7 ?
C16 C15 H15 . . 120.7 ?
C15 C16 C11 . . 121.63(18) ?
C15 C16 H16 . . 119.2 ?
C11 C16 H16 . . 119.2 ?
C36 C31 C32 . . 114.83(17) ?
C36 C31 B1 . . 122.88(17) ?
C32 C31 B1 . . 122.29(17) ?
C33 C32 C31 . . 122.78(18) ?
C33 C32 C37 . . 117.27(17) ?
C31 C32 C37 . . 119.95(17) ?
C34 C33 C32 . . 119.75(18) ?
C34 C33 H33 . . 120.1 ?
C32 C33 H33 . . 120.1 ?
C35 C34 C33 . . 119.64(18) ?
C35 C34 C38 . . 120.26(18) ?
C33 C34 C38 . . 120.05(18) ?
C36 C35 C34 . . 119.81(18) ?
C36 C35 H35 . . 120.1 ?
C34 C35 H35 . . 120.1 ?
C35 C36 C31 . . 123.08(17) ?
C35 C36 C39 . . 117.14(17) ?
C31 C36 C39 . . 119.77(17) ?
F1 C37 F3 . . 106.50(16) ?
F1 C37 F2 . . 106.75(17) ?
F3 C37 F2 . . 106.27(16) ?
F1 C37 C32 . . 112.57(16) ?
F3 C37 C32 . . 112.00(17) ?
F2 C37 C32 . . 112.32(16) ?
F4 C38 F6 . . 108.0(6) ?
F5A C38 F6A . . 106.3(11) ?
F5A C38 F4A . . 106.5(10) ?
F6A C38 F4A . . 103.5(11) ?
F4 C38 F5 . . 106.5(6) ?
F6 C38 F5 . . 106.3(7) ?
F5A C38 C34 . . 115.8(10) ?
F4 C38 C34 . . 113.7(5) ?
F6 C38 C34 . . 110.6(7) ?
F6A C38 C34 . . 112.5(10) ?
F4A C38 C34 . . 111.3(8) ?
F5 C38 C34 . . 111.4(6) ?
F8 C39 F7 . . 107.20(16) ?
F8 C39 F9 . . 106.10(17) ?
F7 C39 F9 . . 105.56(16) ?
F8 C39 C36 . . 112.85(16) ?
F7 C39 C36 . . 112.37(16) ?
F9 C39 C36 . . 112.24(16) ?
C42 C41 C46 . . 121.43(18) ?
C42 C41 N1 . . 119.69(17) ?
C46 C41 N1 . . 118.80(18) ?
C43 C42 C41 . . 118.13(18) ?
C43 C42 C47 . . 120.36(19) ?
C41 C42 C47 . . 121.51(18) ?
C44 C43 C42 . . 121.21(19) ?
C44 C43 H43 . . 119.4 ?
C42 C43 H43 . . 119.4 ?
C43 C44 C45 . . 119.95(19) ?
C43 C44 H44 . . 120.0 ?
C45 C44 H44 . . 120.0 ?
C44 C45 C46 . . 120.70(19) ?
C44 C45 H45 . . 119.7 ?
C46 C45 H45 . . 119.7 ?
C45 C46 C41 . . 118.59(19) ?
C45 C46 C48 . . 120.86(18) ?
C41 C46 C48 . . 120.55(18) ?
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 ?
C52 C51 C56 . . 122.93(18) ?
C52 C51 N2 . . 118.45(17) ?
C56 C51 N2 . . 118.47(17) ?
C51 C52 C53 . . 117.26(19) ?
C51 C52 C57 . . 121.25(18) ?
C53 C52 C57 . . 121.47(19) ?
C54 C53 C52 . . 120.9(2) ?
C54 C53 H53 . . 119.5 ?
C52 C53 H53 . . 119.5 ?
C55 C54 C53 . . 120.5(2) ?
C55 C54 H54 . . 119.7 ?
C53 C54 H54 . . 119.7 ?
C54 C55 C56 . . 120.7(2) ?
C54 C55 H55 . . 119.7 ?
C56 C55 H55 . . 119.7 ?
C55 C56 C51 . . 117.7(2) ?
C55 C56 C58 . . 120.98(19) ?
C51 C56 C58 . . 121.35(18) ?
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 ?
C61 C62 C63 . . 114.8(4) ?
C61 C62 H62A . . 108.6 ?
C63 C62 H62A . . 108.6 ?
C61 C62 H62B . . 108.6 ?
C63 C62 H62B . . 108.6 ?
H62A C62 H62B . . 107.5 ?
C63 C63 C62 2_765 . 113.8(3) ?
C63 C63 H63A 2_765 . 108.8 ?
C62 C63 H63A . . 108.8 ?
C63 C63 H63B 2_765 . 108.8 ?
C62 C63 H63B . . 108.8 ?
H63A C63 H63B . . 107.7 ?
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
B1 C4 . 1.463(3) ?
B1 C3 . 1.523(3) ?
B1 C31 . 1.604(3) ?
N1 C3 . 1.371(2) ?
N1 C41 . 1.429(2) ?
N1 H1 . 0.87(3) ?
N2 C1 . 1.362(2) ?
N2 C4 . 1.382(3) ?
N2 C51 . 1.453(2) ?
Br1 C14 . 1.9023(19) ?
C1 C2 . 1.390(3) ?
C1 C11 . 1.483(3) ?
C2 C3 . 1.398(3) ?
C2 H2 . 0.95 ?
C4 H4 . 0.95 ?
C11 C16 . 1.399(3) ?
C11 C12 . 1.402(3) ?
C12 C13 . 1.384(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.382(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.383(3) ?
C15 C16 . 1.389(3) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C31 C36 . 1.411(3) ?
C31 C32 . 1.414(3) ?
C32 C33 . 1.391(3) ?
C32 C37 . 1.511(3) ?
C33 C34 . 1.388(3) ?
C33 H33 . 0.95 ?
C34 C35 . 1.387(3) ?
C34 C38 . 1.498(3) ?
C35 C36 . 1.386(3) ?
C35 H35 . 0.95 ?
C36 C39 . 1.513(3) ?
C37 F1 . 1.337(2) ?
C37 F3 . 1.340(2) ?
C37 F2 . 1.343(2) ?
C38 F5A . 1.312(11) ?
C38 F4 . 1.313(7) ?
C38 F6 . 1.327(7) ?
C38 F6A . 1.334(11) ?
C38 F4A . 1.336(9) ?
C38 F5 . 1.338(6) ?
C39 F8 . 1.335(2) ?
C39 F7 . 1.336(2) ?
C39 F9 . 1.343(2) ?
C41 C42 . 1.402(3) ?
C41 C46 . 1.404(3) ?
C42 C43 . 1.396(3) ?
C42 C47 . 1.505(3) ?
C43 C44 . 1.386(3) ?
C43 H43 . 0.95 ?
C44 C45 . 1.389(3) ?
C44 H44 . 0.95 ?
C45 C46 . 1.394(3) ?
C45 H45 . 0.95 ?
C46 C48 . 1.508(3) ?
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 C52 . 1.395(3) ?
C51 C56 . 1.395(3) ?
C52 C53 . 1.395(3) ?
C52 C57 . 1.509(3) ?
C53 C54 . 1.384(4) ?
C53 H53 . 0.95 ?
C54 C55 . 1.381(4) ?
C54 H54 . 0.95 ?
C55 C56 . 1.393(3) ?
C55 H55 . 0.95 ?
C56 C58 . 1.504(3) ?
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 . 1.407(7) ?
C61 H61A . 0.98 ?
C61 H61B . 0.98 ?
C61 H61C . 0.98 ?
C62 C63 . 1.518(4) ?
C62 H62A . 0.99 ?
C62 H62B . 0.99 ?
C63 C63 2_765 1.496(6) ?
C63 H63A . 0.99 ?
C63 H63B . 0.99 ?
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 . . . . -0.8(3) ?
C51 N2 C1 C2 . . . . 173.79(17) ?
C4 N2 C1 C11 . . . . 179.87(16) ?
C51 N2 C1 C11 . . . . -5.5(3) ?
N2 C1 C2 C3 . . . . 0.0(3) ?
C11 C1 C2 C3 . . . . 179.25(17) ?
C41 N1 C3 C2 . . . . 4.8(3) ?
C41 N1 C3 B1 . . . . -175.36(18) ?
C1 C2 C3 N1 . . . . -178.66(17) ?
C1 C2 C3 B1 . . . . 1.5(3) ?
C4 B1 C3 N1 . . . . 178.15(17) ?
C31 B1 C3 N1 . . . . -0.2(3) ?
C4 B1 C3 C2 . . . . -2.0(2) ?
C31 B1 C3 C2 . . . . 179.63(17) ?
C1 N2 C4 B1 . . . . 0.1(3) ?
C51 N2 C4 B1 . . . . -174.84(17) ?
C3 B1 C4 N2 . . . . 1.3(3) ?
C31 B1 C4 N2 . . . . 179.68(17) ?
N2 C1 C11 C16 . . . . 135.14(18) ?
C2 C1 C11 C16 . . . . -44.1(2) ?
N2 C1 C11 C12 . . . . -47.4(3) ?
C2 C1 C11 C12 . . . . 133.3(2) ?
C16 C11 C12 C13 . . . . -2.3(3) ?
C1 C11 C12 C13 . . . . -179.76(18) ?
C11 C12 C13 C14 . . . . 1.4(3) ?
C12 C13 C14 C15 . . . . 0.9(3) ?
C12 C13 C14 Br1 . . . . -178.39(14) ?
C13 C14 C15 C16 . . . . -2.0(3) ?
Br1 C14 C15 C16 . . . . 177.21(14) ?
C14 C15 C16 C11 . . . . 1.0(3) ?
C12 C11 C16 C15 . . . . 1.1(3) ?
C1 C11 C16 C15 . . . . 178.63(17) ?
C4 B1 C31 C36 . . . . 98.5(2) ?
C3 B1 C31 C36 . . . . -83.3(2) ?
C4 B1 C31 C32 . . . . -81.3(2) ?
C3 B1 C31 C32 . . . . 96.9(2) ?
C36 C31 C32 C33 . . . . 1.8(3) ?
B1 C31 C32 C33 . . . . -178.36(17) ?
C36 C31 C32 C37 . . . . -178.36(17) ?
B1 C31 C32 C37 . . . . 1.5(3) ?
C31 C32 C33 C34 . . . . 1.0(3) ?
C37 C32 C33 C34 . . . . -178.82(17) ?
C32 C33 C34 C35 . . . . -2.6(3) ?
C32 C33 C34 C38 . . . . 174.91(18) ?
C33 C34 C35 C36 . . . . 1.3(3) ?
C38 C34 C35 C36 . . . . -176.24(18) ?
C34 C35 C36 C31 . . . . 1.8(3) ?
C34 C35 C36 C39 . . . . -176.96(17) ?
C32 C31 C36 C35 . . . . -3.2(3) ?
B1 C31 C36 C35 . . . . 176.95(18) ?
C32 C31 C36 C39 . . . . 175.50(17) ?
B1 C31 C36 C39 . . . . -4.3(3) ?
C33 C32 C37 F1 . . . . 130.67(18) ?
C31 C32 C37 F1 . . . . -49.2(2) ?
C33 C32 C37 F3 . . . . 10.7(2) ?
C31 C32 C37 F3 . . . . -169.16(17) ?
C33 C32 C37 F2 . . . . -108.8(2) ?
C31 C32 C37 F2 . . . . 71.3(2) ?
C35 C34 C38 F5A . . . . -11.4(15) ?
C33 C34 C38 F5A . . . . 171.1(14) ?
C35 C34 C38 F4 . . . . -146.1(8) ?
C33 C34 C38 F4 . . . . 36.4(9) ?
C35 C34 C38 F6 . . . . 92.3(8) ?
C33 C34 C38 F6 . . . . -85.2(8) ?
C35 C34 C38 F6A . . . . 111.1(15) ?
C33 C34 C38 F6A . . . . -66.4(15) ?
C35 C34 C38 F4A . . . . -133.2(8) ?
C33 C34 C38 F4A . . . . 49.3(8) ?
C35 C34 C38 F5 . . . . -25.7(7) ?
C33 C34 C38 F5 . . . . 156.8(6) ?
C35 C36 C39 F8 . . . . -120.21(19) ?
C31 C36 C39 F8 . . . . 61.0(2) ?
C35 C36 C39 F7 . . . . 1.2(3) ?
C31 C36 C39 F7 . . . . -177.62(16) ?
C35 C36 C39 F9 . . . . 119.95(19) ?
C31 C36 C39 F9 . . . . -58.8(2) ?
C3 N1 C41 C42 . . . . 72.3(3) ?
C3 N1 C41 C46 . . . . -111.1(2) ?
C46 C41 C42 C43 . . . . 0.1(3) ?
N1 C41 C42 C43 . . . . 176.68(17) ?
C46 C41 C42 C47 . . . . -179.37(17) ?
N1 C41 C42 C47 . . . . -2.8(3) ?
C41 C42 C43 C44 . . . . 0.0(3) ?
C47 C42 C43 C44 . . . . 179.48(18) ?
C42 C43 C44 C45 . . . . -0.5(3) ?
C43 C44 C45 C46 . . . . 0.8(3) ?
C44 C45 C46 C41 . . . . -0.7(3) ?
C44 C45 C46 C48 . . . . 179.02(18) ?
C42 C41 C46 C45 . . . . 0.2(3) ?
N1 C41 C46 C45 . . . . -176.35(17) ?
C42 C41 C46 C48 . . . . -179.50(18) ?
N1 C41 C46 C48 . . . . 3.9(3) ?
C1 N2 C51 C52 . . . . -78.4(2) ?
C4 N2 C51 C52 . . . . 96.5(2) ?
C1 N2 C51 C56 . . . . 105.9(2) ?
C4 N2 C51 C56 . . . . -79.2(2) ?
C56 C51 C52 C53 . . . . -1.3(3) ?
N2 C51 C52 C53 . . . . -176.72(18) ?
C56 C51 C52 C57 . . . . 177.31(19) ?
N2 C51 C52 C57 . . . . 1.9(3) ?
C51 C52 C53 C54 . . . . -0.8(3) ?
C57 C52 C53 C54 . . . . -179.4(2) ?
C52 C53 C54 C55 . . . . 1.5(4) ?
C53 C54 C55 C56 . . . . -0.2(4) ?
C54 C55 C56 C51 . . . . -1.7(3) ?
C54 C55 C56 C58 . . . . 177.7(2) ?
C52 C51 C56 C55 . . . . 2.5(3) ?
N2 C51 C56 C55 . . . . 177.96(19) ?
C52 C51 C56 C58 . . . . -176.9(2) ?
N2 C51 C56 C58 . . . . -1.5(3) ?
C61 C62 C63 C63 . . . 2_765 173.9(4) ?
