#------------------------------------------------------------------------------
#$Date: 2019-11-03 16:34:19 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221887 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/88/4128822.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_4128822
loop_
_publ_author_name
'Su, Yuanting'
'Huan Do, Dinh Cao'
'Li, Yongxin'
'Kinjo, Rei'
_publ_section_title
;
 Metal-Free Selective Borylation of Arenes by a Diazadiborinine via
 C-H/C-F Bond Activation and Dearomatization.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13729
_journal_page_last               13733
_journal_paper_doi               10.1021/jacs.9b06022
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C77.88 H69.7 B2 Cl N4'
_chemical_formula_weight         1118.71
_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
_cell_angle_alpha                94.8002(15)
_cell_angle_beta                 102.9608(14)
_cell_angle_gamma                92.4223(12)
_cell_formula_units_Z            2
_cell_length_a                   12.0361(4)
_cell_length_b                   15.2317(6)
_cell_length_c                   16.9141(7)
_cell_measurement_reflns_used    5743
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      30.4345
_cell_measurement_theta_min      2.3264
_cell_volume                     3005.3(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2017)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.1292
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            42262
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         2.27
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.441
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     807
_refine_ls_number_reflns         18194
_refine_ls_number_restraints     212
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1636
_refine_ls_R_factor_gt           0.0772
_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)+(0.0771P)²+1.1977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1641
_refine_ls_wR_factor_ref         0.2106
_reflns_number_gt                9364
_reflns_number_total             18194
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b06022_si_015.cif
_cod_data_source_block           rei1188m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_formula_sum        'C77.88 H69.70 B2 Cl N4'
_cod_database_code               4128822
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 0.5197(2) 0.46994(18) 0.29399(17) 0.0240(6) Uani d . . . 1.0 . .
B B2 0.7251(2) 0.43308(18) 0.25731(18) 0.0235(6) Uani d . . . 1.0 . .
C C1 0.3922(2) 0.49102(16) 0.30069(16) 0.0268(5) Uani d . . . 1.0 . .
C C2 0.3059(2) 0.49022(16) 0.23004(17) 0.0286(6) Uani d . . . 1.0 . .
H H2 0.3244 0.478581 0.178583 0.034 Uiso calc U . R 1.0 . .
C C3 0.1945(2) 0.50584(17) 0.23257(19) 0.0349(6) Uani d . . . 1.0 . .
H H3 0.137144 0.503171 0.183492 0.042 Uiso calc U . R 1.0 . .
C C4 0.1670(2) 0.52527(19) 0.3065(2) 0.0409(7) Uani d . . . 1.0 . .
H H4 0.090393 0.535663 0.308625 0.049 Uiso calc U . R 1.0 . .
C C5 0.2513(2) 0.52964(19) 0.3779(2) 0.0426(8) Uani d . . . 1.0 . .
H H5 0.232962 0.544808 0.428892 0.051 Uiso calc U . R 1.0 . .
C C6 0.3626(2) 0.51181(18) 0.37472(18) 0.0340(6) Uani d . . . 1.0 . .
H H6 0.419497 0.513841 0.423983 0.041 Uiso calc U . R 1.0 . .
C C7 0.67025(19) 0.52176(15) 0.22535(15) 0.0231(5) Uani d . . . 1.0 . .
C C8 0.6334(2) 0.66037(16) 0.19659(16) 0.0268(5) Uani d . . . 1.0 . .
C C9 0.55040(19) 0.62818(16) 0.23231(15) 0.0247(5) Uani d . . . 1.0 . .
C C10 0.4581(2) 0.67912(16) 0.25486(16) 0.0261(5) Uani d . . . 1.0 . .
C C11 0.3753(2) 0.71094(18) 0.19585(17) 0.0323(6) Uani d . . . 1.0 . .
H H11 0.374324 0.696167 0.139985 0.039 Uiso calc U . R 1.0 . .
C C12 0.2933(2) 0.76428(18) 0.21659(19) 0.0359(6) Uani d . . . 1.0 . .
H H12 0.237104 0.78561 0.174963 0.043 Uiso calc U . R 1.0 . .
C C13 0.2933(3) 0.7861(2) 0.2966(2) 0.0447(8) Uani d . . . 1.0 . .
H H13 0.237725 0.822923 0.310949 0.054 Uiso calc U . R 1.0 . .
C C14 0.3744(3) 0.7543(3) 0.3555(2) 0.0645(11) Uani d . . . 1.0 . .
H H14 0.374548 0.768977 0.411288 0.077 Uiso calc U . R 1.0 . .
C C15 0.4562(3) 0.7011(2) 0.33542(19) 0.0477(8) Uani d . . . 1.0 . .
H H15 0.51164 0.679427 0.377395 0.057 Uiso calc U . R 1.0 . .
C C16 0.6562(2) 0.75017(17) 0.17521(18) 0.0326(6) Uani d . . . 1.0 . .
C C17 0.6851(2) 0.7661(2) 0.1017(2) 0.0422(7) Uani d . . . 1.0 . .
H H17 0.688613 0.717885 0.063072 0.051 Uiso calc U . R 1.0 . .
C C18 0.7087(3) 0.8513(2) 0.0847(3) 0.0586(10) Uani d . . . 1.0 . .
H H18 0.73009 0.861045 0.035222 0.07 Uiso calc U . R 1.0 . .
C C19 0.7013(3) 0.9207(2) 0.1381(3) 0.0660(12) Uani d . . . 1.0 . .
H H19 0.715206 0.979031 0.124971 0.079 Uiso calc U . R 1.0 . .
C C20 0.6737(3) 0.9079(2) 0.2116(3) 0.0606(10) Uani d . . . 1.0 . .
H H20 0.669472 0.957119 0.248988 0.073 Uiso calc U . R 1.0 . .
C C21 0.6520(2) 0.82228(18) 0.2306(2) 0.0425(7) Uani d . . . 1.0 . .
H H21 0.634335 0.813202 0.281389 0.051 Uiso calc U . R 1.0 . .
C C22 0.8013(2) 0.59736(16) 0.15269(16) 0.0260(5) Uani d . . . 1.0 . .
C C23 0.9051(2) 0.63768(16) 0.19829(16) 0.0279(5) Uani d . . . 1.0 . .
C C24 0.9921(2) 0.64903(17) 0.15754(18) 0.0319(6) Uani d . . . 1.0 . .
H H24 1.063573 0.676155 0.187079 0.038 Uiso calc U . R 1.0 . .
C C25 0.9786(2) 0.62230(18) 0.07553(18) 0.0347(6) Uani d . . . 1.0 . .
C C26 0.8744(2) 0.58256(19) 0.03281(18) 0.0381(7) Uani d . . . 1.0 . .
H H26 0.864509 0.56357 -0.02342 0.046 Uiso calc U . R 1.0 . .
C C27 0.7836(2) 0.56970(18) 0.07026(17) 0.0322(6) Uani d . . . 1.0 . .
C C28 0.6689(3) 0.5305(2) 0.02112(19) 0.0467(8) Uani d . . . 1.0 . .
H H28A 0.633322 0.493955 0.054764 0.07 Uiso calc U . R 1.0 . .
H H28B 0.679569 0.494076 -0.026863 0.07 Uiso calc U . R 1.0 . .
H H28C 0.619606 0.578161 0.003592 0.07 Uiso calc U . R 1.0 . .
C C29 1.0756(3) 0.6372(2) 0.0338(2) 0.0479(8) Uani d . . . 1.0 . .
H H29A 1.085473 0.700201 0.027215 0.072 Uiso calc U . R 1.0 . .
H H29B 1.057935 0.603419 -0.019869 0.072 Uiso calc U . R 1.0 . .
H H29C 1.146189 0.61778 0.066989 0.072 Uiso calc U . R 1.0 . .
C C30 0.9205(2) 0.66805(19) 0.28682(17) 0.0353(6) Uani d . . . 1.0 . .
H H30A 0.998516 0.693828 0.308489 0.053 Uiso calc U . R 1.0 . .
H H30B 0.907175 0.617651 0.316651 0.053 Uiso calc U . R 1.0 . .
H H30C 0.865922 0.712558 0.293264 0.053 Uiso calc U . R 1.0 . .
C C31 0.62463(19) 0.35772(15) 0.22748(14) 0.0217(5) Uani d . . . 1.0 . .
C C32 0.50903(19) 0.23477(16) 0.19635(15) 0.0240(5) Uani d . . . 1.0 . .
C C33 0.44907(19) 0.30064(15) 0.22232(15) 0.0228(5) Uani d . . . 1.0 . .
C C34 0.32477(19) 0.29155(15) 0.21986(16) 0.0253(5) Uani d . . . 1.0 . .
C C35 0.2805(2) 0.29373(17) 0.28896(18) 0.0323(6) Uani d . . . 1.0 . .
H H35 0.330003 0.300471 0.341696 0.039 Uiso calc U . R 1.0 . .
C C36 0.1620(2) 0.28588(18) 0.2800(2) 0.0432(8) Uani d . . . 1.0 . .
H H36 0.130716 0.288809 0.326936 0.052 Uiso calc U . R 1.0 . .
C C37 0.0907(2) 0.27396(19) 0.2038(2) 0.0467(8) Uani d . . . 1.0 . .
H H37 0.010378 0.269411 0.198429 0.056 Uiso calc U . R 1.0 . .
C C38 0.1341(2) 0.26857(19) 0.1357(2) 0.0428(7) Uani d . . . 1.0 . .
H H38 0.084238 0.258749 0.08313 0.051 Uiso calc U . R 1.0 . .
C C39 0.2509(2) 0.27750(17) 0.14365(18) 0.0333(6) Uani d . . . 1.0 . .
H H39 0.281035 0.273962 0.096237 0.04 Uiso calc U . R 1.0 . .
C C40 0.4741(2) 0.13997(16) 0.17629(16) 0.0270(5) Uani d . . . 1.0 . .
C C41 0.4613(2) 0.09680(17) 0.09925(18) 0.0340(6) Uani d . . . 1.0 . .
H H41 0.478879 0.127887 0.056749 0.041 Uiso calc U . R 1.0 . .
C C42 0.4230(2) 0.00854(18) 0.0835(2) 0.0402(7) Uani d . . . 1.0 . .
H H42 0.412982 -0.020105 0.030027 0.048 Uiso calc U . R 1.0 . .
C C43 0.3996(2) -0.03738(18) 0.1444(2) 0.0401(7) Uani d . . . 1.0 . .
H H43 0.374649 -0.098091 0.133498 0.048 Uiso calc U . R 1.0 . .
C C44 0.4120(2) 0.00385(19) 0.22129(19) 0.0404(7) Uani d . . . 1.0 . .
H H44 0.395165 -0.028199 0.263436 0.048 Uiso calc U . R 1.0 . .
C C45 0.4493(2) 0.09243(18) 0.23777(18) 0.0350(6) Uani d . . . 1.0 . .
H H45 0.457895 0.120745 0.291204 0.042 Uiso calc U . R 1.0 . .
C C46 0.6971(2) 0.22705(16) 0.15884(16) 0.0259(5) Uani d . . . 1.0 . .
C C47 0.7760(2) 0.17403(16) 0.20107(17) 0.0302(6) Uani d . . . 1.0 . .
C C48 0.8459(2) 0.12901(17) 0.1585(2) 0.0381(7) Uani d . . . 1.0 . .
H H48 0.901088 0.092981 0.186739 0.046 Uiso calc U . R 1.0 . .
C C49 0.8373(2) 0.13523(19) 0.0762(2) 0.0413(7) Uani d . . . 1.0 . .
C C50 0.7578(2) 0.18819(19) 0.03640(18) 0.0376(7) Uani d . . . 1.0 . .
H H50 0.751421 0.192938 -0.02007 0.045 Uiso calc U . R 1.0 . .
C C51 0.6860(2) 0.23527(17) 0.07633(17) 0.0319(6) Uani d . . . 1.0 . .
C C52 0.5989(3) 0.2917(2) 0.03005(19) 0.0471(8) Uani d . . . 1.0 . .
H H52A 0.544018 0.307647 0.06289 0.071 Uiso calc U . R 1.0 . .
H H52B 0.558601 0.258649 -0.021304 0.071 Uiso calc U . R 1.0 . .
H H52C 0.637595 0.345411 0.018469 0.071 Uiso calc U . R 1.0 . .
C C53 0.9117(3) 0.0831(2) 0.0307(2) 0.0629(11) Uani d . . . 1.0 . .
H H53A 0.870097 0.027675 0.004669 0.094 Uiso calc U . R 1.0 . .
H H53B 0.981722 0.070066 0.069073 0.094 Uiso calc U . R 1.0 . .
H H53C 0.931496 0.117737 -0.010992 0.094 Uiso calc U . R 1.0 . .
C C54 0.7896(3) 0.1680(2) 0.29050(18) 0.0447(7) Uani d . . . 1.0 . .
H H54A 0.832205 0.221263 0.320756 0.067 Uiso calc U . R 1.0 . .
H H54B 0.831451 0.116034 0.306306 0.067 Uiso calc U . R 1.0 . .
H H54C 0.714111 0.162773 0.303035 0.067 Uiso calc U . R 1.0 . .
C C55 0.6171(2) 0.45924(17) 0.37796(15) 0.0267(5) Uani d . . . 1.0 . .
H H55 0.617862 0.512078 0.417419 0.032 Uiso calc U . R 1.0 . .
C C56 0.7388(2) 0.45421(16) 0.35976(15) 0.0260(5) Uani d . . . 1.0 . .
H H56 0.776436 0.51499 0.374671 0.031 Uiso calc U . R 1.0 . .
C C57 0.8159(2) 0.39417(17) 0.41008(15) 0.0292(5) Uani d . . . 1.0 . .
C C58 0.9327(2) 0.40627(18) 0.42512(16) 0.0321(6) Uani d . . . 1.0 . .
H H58 0.965047 0.456772 0.407157 0.039 Uiso calc U . R 1.0 . .
C C59 1.0071(2) 0.3464(2) 0.46639(17) 0.0386(7) Uani d . . . 1.0 . .
C C60 1.1271(3) 0.3583(2) 0.48076(19) 0.0476(8) Uani d . . . 1.0 . .
H H60 1.160381 0.409744 0.465056 0.057 Uiso calc U . R 1.0 . .
C C61 1.1968(3) 0.2966(3) 0.5171(2) 0.0566(9) Uani d . . . 1.0 . .
H H61 1.27743 0.305618 0.526025 0.068 Uiso calc U . R 1.0 . .
C C62 1.1483(3) 0.2199(3) 0.5411(2) 0.0613(10) Uani d . . . 1.0 . .
H H62 1.19623 0.17661 0.564945 0.074 Uiso calc U . R 1.0 . .
C C63 1.0329(3) 0.2080(2) 0.5300(2) 0.0552(9) Uani d . . . 1.0 . .
H H63 1.00121 0.156858 0.547364 0.066 Uiso calc U . R 1.0 . .
C C64 0.9590(3) 0.2708(2) 0.49297(17) 0.0418(7) Uani d . . . 1.0 . .
C C65 0.8400(3) 0.2620(2) 0.48242(17) 0.0405(7) Uani d . . . 1.0 . .
H H65 0.807306 0.213823 0.503497 0.049 Uiso calc U . R 1.0 . .
C C66 0.7692(2) 0.32061(18) 0.44265(16) 0.0335(6) Uani d . . . 1.0 . .
C C67 0.6465(2) 0.31404(19) 0.43708(17) 0.0368(6) Uani d . . . 1.0 . .
H H67 0.61265 0.261567 0.450628 0.044 Uiso calc U . R 1.0 . .
C C68 0.5804(2) 0.37941(18) 0.41357(16) 0.0327(6) Uani d . . . 1.0 . .
H H68 0.504021 0.374924 0.419932 0.039 Uiso calc U . R 1.0 . .
C C69 0.1407(3) 1.0459(2) 0.2669(3) 0.0628(10) Uani d . . . 1.0 . .
H H69 0.195948 1.088678 0.259086 0.075 Uiso calc U . R 1.0 . .
C C70 0.0939(4) 1.0579(3) 0.3337(3) 0.0776(12) Uani d . . . 1.0 . .
H H70 0.117918 1.108219 0.371761 0.093 Uiso calc U . R 1.0 . .
C C71 0.0143(4) 0.9988(4) 0.3456(4) 0.1006(17) Uani d . . . 1.0 . .
H H71 -0.017542 1.00733 0.391987 0.121 Uiso calc U . R 1.0 . .
C C72 -0.0207(4) 0.9263(4) 0.2905(4) 0.1001(19) Uani d . . . 1.0 . .
H H72 -0.077125 0.884882 0.298992 0.12 Uiso calc U . R 1.0 . .
C C73 0.0253(4) 0.9124(3) 0.2222(4) 0.0893(15) Uani d . . . 1.0 . .
H H73 0.000244 0.862446 0.18377 0.107 Uiso calc U . R 1.0 . .
C C74 0.1094(3) 0.9739(3) 0.2117(3) 0.0689(11) Uani d . . . 1.0 . .
H H74 0.144033 0.965532 0.166619 0.083 Uiso calc U . R 1.0 . .
C C75 0.4591(10) -0.0223(7) 0.5152(7) 0.164(3) Uani d U P D 0.705(5) A 1
H H75A 0.494908 -0.0444 0.567768 0.197 Uiso calc U P R 0.705(5) A 1
H H75B 0.423252 -0.073331 0.476472 0.197 Uiso calc U P R 0.705(5) A 1
C C76 0.3722(10) 0.0397(8) 0.5270(8) 0.169(3) Uani d U P D 0.705(5) A 1
H H76A 0.345591 0.068136 0.476133 0.202 Uiso calc U P R 0.705(5) A 1
H H76B 0.40721 0.086517 0.570686 0.202 Uiso calc U P R 0.705(5) A 1
C C77 0.2672(9) -0.0071(6) 0.5501(6) 0.137(3) Uani d U P D 0.705(5) A 1
H H77A 0.215686 -0.036006 0.500632 0.206 Uiso calc U P R 0.705(5) A 1
H H77B 0.226509 0.036796 0.576325 0.206 Uiso calc U P R 0.705(5) A 1
H H77C 0.293798 -0.051359 0.587667 0.206 Uiso calc U P R 0.705(5) A 1
C C78 0.3455(16) 0.0642(12) 0.4346(9) 0.166(4) Uani d U P G 0.295(5) A 2
H H78 0.329189 0.079892 0.380158 0.199 Uiso calc U P R 0.295(5) A 2
C C79 0.4197(15) 0.1185(9) 0.4958(12) 0.158(4) Uani d U P G 0.295(5) A 2
H H79 0.454049 0.171255 0.483212 0.189 Uiso calc U P R 0.295(5) A 2
C C80 0.4436(15) 0.0955(11) 0.5754(11) 0.167(4) Uani d U P G 0.295(5) A 2
H H80 0.494302 0.132611 0.617246 0.2 Uiso calc U P R 0.295(5) A 2
C C81 0.3934(17) 0.0183(12) 0.5938(9) 0.163(4) Uani d U P G 0.295(5) A 2
H H81 0.409695 0.002604 0.648228 0.196 Uiso calc U P R 0.295(5) A 2
C C82 0.3192(16) -0.0360(9) 0.5326(12) 0.166(4) Uani d U P G 0.295(5) A 2
H H82 0.284834 -0.088761 0.545176 0.199 Uiso calc U P R 0.295(5) A 2
C C83 0.2953(15) -0.0130(11) 0.4530(11) 0.164(4) Uani d U P G 0.295(5) A 2
H H83 0.24458 -0.050118 0.411141 0.196 Uiso calc U P R 0.295(5) A 2
Cl Cl1 0.85925(5) 0.40948(4) 0.22583(4) 0.02731(15) Uani d . . . 1.0 . .
N N1 0.57339(16) 0.54171(13) 0.24794(12) 0.0227(4) Uani d . . . 1.0 . .
N N2 0.70632(16) 0.59167(13) 0.19160(13) 0.0251(4) Uani d . . . 1.0 . .
N N3 0.52182(15) 0.37735(12) 0.24135(12) 0.0214(4) Uani d . . . 1.0 . .
N N4 0.61820(16) 0.27165(13) 0.19861(12) 0.0223(4) Uani d . . . 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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_
_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
N1 B1 C1 . 111.6(2)
N1 B1 N3 . 105.21(18)
C1 B1 N3 . 111.68(19)
N1 B1 C55 . 105.87(19)
C1 B1 C55 . 119.2(2)
N3 B1 C55 . 102.02(19)
C31 B2 C7 . 104.89(19)
C31 B2 C56 . 106.02(19)
C7 B2 C56 . 100.85(19)
C31 B2 Cl1 . 114.82(18)
C7 B2 Cl1 . 113.86(17)
C56 B2 Cl1 . 114.97(17)
C6 C1 C2 . 117.2(2)
C6 C1 B1 . 123.0(2)
C2 C1 B1 . 119.8(2)
C3 C2 C1 . 122.0(2)
C3 C2 H2 . 119.0
C1 C2 H2 . 119.0
C4 C3 C2 . 119.7(3)
C4 C3 H3 . 120.1
C2 C3 H3 . 120.1
C3 C4 C5 . 119.9(2)
C3 C4 H4 . 120.1
C5 C4 H4 . 120.1
C4 C5 C6 . 119.9(3)
C4 C5 H5 . 120.0
C6 C5 H5 . 120.0
C5 C6 C1 . 121.2(3)
C5 C6 H6 . 119.4
C1 C6 H6 . 119.4
N1 C7 N2 . 108.0(2)
N1 C7 B2 . 115.6(2)
N2 C7 B2 . 135.4(2)
C9 C8 N2 . 106.0(2)
C9 C8 C16 . 130.1(2)
N2 C8 C16 . 123.5(2)
C8 C9 N1 . 107.6(2)
C8 C9 C10 . 125.6(2)
N1 C9 C10 . 126.7(2)
C11 C10 C15 . 117.9(2)
C11 C10 C9 . 120.7(2)
C15 C10 C9 . 121.3(2)
C10 C11 C12 . 121.2(3)
C10 C11 H11 . 119.4
C12 C11 H11 . 119.4
C13 C12 C11 . 120.3(3)
C13 C12 H12 . 119.9
C11 C12 H12 . 119.9
C12 C13 C14 . 119.0(3)
C12 C13 H13 . 120.5
C14 C13 H13 . 120.5
C13 C14 C15 . 121.1(3)
C13 C14 H14 . 119.5
C15 C14 H14 . 119.5
C10 C15 C14 . 120.6(3)
C10 C15 H15 . 119.7
C14 C15 H15 . 119.7
C21 C16 C17 . 118.2(3)
C21 C16 C8 . 119.3(3)
C17 C16 C8 . 122.5(3)
C18 C17 C16 . 120.8(3)
C18 C17 H17 . 119.6
C16 C17 H17 . 119.6
C19 C18 C17 . 120.3(4)
C19 C18 H18 . 119.8
C17 C18 H18 . 119.8
C18 C19 C20 . 120.8(3)
C18 C19 H19 . 119.6
C20 C19 H19 . 119.6
C19 C20 C21 . 119.7(4)
C19 C20 H20 . 120.2
C21 C20 H20 . 120.2
C16 C21 C20 . 120.2(3)
C16 C21 H21 . 119.9
C20 C21 H21 . 119.9
C27 C22 C23 . 122.6(2)
C27 C22 N2 . 119.0(2)
C23 C22 N2 . 118.2(2)
C24 C23 C22 . 117.0(2)
C24 C23 C30 . 121.8(2)
C22 C23 C30 . 121.1(2)
C25 C24 C23 . 122.4(2)
C25 C24 H24 . 118.8
C23 C24 H24 . 118.8
C24 C25 C26 . 118.6(2)
C24 C25 C29 . 120.4(3)
C26 C25 C29 . 121.1(3)
C25 C26 C27 . 121.7(3)
C25 C26 H26 . 119.2
C27 C26 H26 . 119.2
C22 C27 C26 . 117.7(2)
C22 C27 C28 . 121.7(2)
C26 C27 C28 . 120.5(3)
C27 C28 H28A . 109.5
C27 C28 H28B . 109.5
H28A C28 H28B . 109.5
C27 C28 H28C . 109.5
H28A C28 H28C . 109.5
H28B C28 H28C . 109.5
C25 C29 H29A . 109.5
C25 C29 H29B . 109.5
H29A C29 H29B . 109.5
C25 C29 H29C . 109.5
H29A C29 H29C . 109.5
H29B C29 H29C . 109.5
C23 C30 H30A . 109.5
C23 C30 H30B . 109.5
H30A C30 H30B . 109.5
C23 C30 H30C . 109.5
H30A C30 H30C . 109.5
H30B C30 H30C . 109.5
N3 C31 N4 . 108.23(19)
N3 C31 B2 . 116.1(2)
N4 C31 B2 . 135.2(2)
C33 C32 N4 . 106.9(2)
C33 C32 C40 . 128.6(2)
N4 C32 C40 . 124.3(2)
C32 C33 N3 . 107.61(19)
C32 C33 C34 . 124.0(2)
N3 C33 C34 . 128.0(2)
C39 C34 C35 . 119.2(2)
C39 C34 C33 . 117.1(2)
C35 C34 C33 . 123.7(2)
C34 C35 C36 . 119.2(3)
C34 C35 H35 . 120.4
C36 C35 H35 . 120.4
C37 C36 C35 . 120.3(3)
C37 C36 H36 . 119.9
C35 C36 H36 . 119.9
C38 C37 C36 . 120.7(3)
C38 C37 H37 . 119.6
C36 C37 H37 . 119.6
C37 C38 C39 . 119.5(3)
C37 C38 H38 . 120.2
C39 C38 H38 . 120.2
C38 C39 C34 . 121.0(3)
C38 C39 H39 . 119.5
C34 C39 H39 . 119.5
C41 C40 C45 . 118.5(2)
C41 C40 C32 . 123.4(2)
C45 C40 C32 . 118.1(2)
C40 C41 C42 . 120.6(3)
C40 C41 H41 . 119.7
C42 C41 H41 . 119.7
C43 C42 C41 . 120.3(3)
C43 C42 H42 . 119.9
C41 C42 H42 . 119.9
C42 C43 C44 . 120.2(3)
C42 C43 H43 . 119.9
C44 C43 H43 . 119.9
C43 C44 C45 . 120.1(3)
C43 C44 H44 . 119.9
C45 C44 H44 . 119.9
C44 C45 C40 . 120.3(3)
C44 C45 H45 . 119.8
C40 C45 H45 . 119.8
C47 C46 C51 . 121.9(2)
C47 C46 N4 . 120.5(2)
C51 C46 N4 . 117.4(2)
C46 C47 C48 . 118.0(3)
C46 C47 C54 . 121.4(2)
C48 C47 C54 . 120.6(3)
C49 C48 C47 . 121.8(3)
C49 C48 H48 . 119.1
C47 C48 H48 . 119.1
C50 C49 C48 . 118.4(2)
C50 C49 C53 . 120.8(3)
C48 C49 C53 . 120.7(3)
C49 C50 C51 . 122.1(3)
C49 C50 H50 . 119.0
C51 C50 H50 . 119.0
C46 C51 C50 . 117.7(3)
C46 C51 C52 . 122.0(2)
C50 C51 C52 . 120.3(3)
C51 C52 H52A . 109.5
C51 C52 H52B . 109.5
H52A C52 H52B . 109.5
C51 C52 H52C . 109.5
H52A C52 H52C . 109.5
H52B C52 H52C . 109.5
C49 C53 H53A . 109.5
C49 C53 H53B . 109.5
H53A C53 H53B . 109.5
C49 C53 H53C . 109.5
H53A C53 H53C . 109.5
H53B C53 H53C . 109.5
C47 C54 H54A . 109.5
C47 C54 H54B . 109.5
H54A C54 H54B . 109.5
C47 C54 H54C . 109.5
H54A C54 H54C . 109.5
H54B C54 H54C . 109.5
C68 C55 C56 . 113.1(2)
C68 C55 B1 . 107.2(2)
C56 C55 B1 . 110.97(19)
C68 C55 H55 . 108.5
C56 C55 H55 . 108.5
B1 C55 H55 . 108.5
C57 C56 C55 . 114.9(2)
C57 C56 B2 . 114.02(19)
C55 C56 B2 . 109.08(19)
C57 C56 H56 . 106.0
C55 C56 H56 . 106.0
B2 C56 H56 . 106.0
C58 C57 C66 . 117.6(2)
C58 C57 C56 . 121.6(2)
C66 C57 C56 . 120.8(2)
C57 C58 C59 . 122.7(3)
C57 C58 H58 . 118.6
C59 C58 H58 . 118.6
C60 C59 C64 . 118.6(3)
C60 C59 C58 . 122.7(3)
C64 C59 C58 . 118.8(3)
C61 C60 C59 . 121.3(3)
C61 C60 H60 . 119.4
C59 C60 H60 . 119.4
C60 C61 C62 . 119.9(3)
C60 C61 H61 . 120.0
C62 C61 H61 . 120.0
C63 C62 C61 . 120.0(3)
C63 C62 H62 . 120.0
C61 C62 H62 . 120.0
C62 C63 C64 . 121.2(4)
C62 C63 H63 . 119.4
C64 C63 H63 . 119.4
C65 C64 C59 . 118.2(3)
C65 C64 C63 . 122.8(3)
C59 C64 C63 . 119.0(3)
C66 C65 C64 . 122.2(3)
C66 C65 H65 . 118.9
C64 C65 H65 . 118.9
C65 C66 C57 . 120.3(3)
C65 C66 C67 . 121.5(3)
C57 C66 C67 . 118.1(2)
C68 C67 C66 . 122.0(3)
C68 C67 H67 . 119.0
C66 C67 H67 . 119.0
C67 C68 C55 . 125.1(2)
C67 C68 H68 . 117.4
C55 C68 H68 . 117.4
C74 C69 C70 . 121.3(4)
C74 C69 H69 . 119.4
C70 C69 H69 . 119.4
C71 C70 C69 . 120.5(5)
C71 C70 H70 . 119.7
C69 C70 H70 . 119.7
C70 C71 C72 . 119.8(5)
C70 C71 H71 . 120.1
C72 C71 H71 . 120.1
C71 C72 C73 . 121.0(5)
C71 C72 H72 . 119.5
C73 C72 H72 . 119.5
C72 C73 C74 . 118.3(5)
C72 C73 H73 . 120.8
C74 C73 H73 . 120.8
C69 C74 C73 . 119.1(4)
C69 C74 H74 . 120.5
C73 C74 H74 . 120.5
C75 C75 C76 2_656 108.2(13)
C75 C75 H75A 2_656 110.1
C76 C75 H75A . 110.1
C75 C75 H75B 2_656 110.1
C76 C75 H75B . 110.1
H75A C75 H75B . 108.4
C75 C76 C77 . 112.3(9)
C75 C76 H76A . 109.1
C77 C76 H76A . 109.1
C75 C76 H76B . 109.1
C77 C76 H76B . 109.1
H76A C76 H76B . 107.9
C76 C77 H77A . 109.5
C76 C77 H77B . 109.5
H77A C77 H77B . 109.5
C76 C77 H77C . 109.5
H77A C77 H77C . 109.5
H77B C77 H77C . 109.5
C79 C78 C83 . 120.0
C79 C78 H78 . 120.0
C83 C78 H78 . 120.0
C80 C79 C78 . 120.0
C80 C79 H79 . 120.0
C78 C79 H79 . 120.0
C81 C80 C79 . 120.0
C81 C80 H80 . 120.0
C79 C80 H80 . 120.0
C82 C81 C80 . 120.0
C82 C81 H81 . 120.0
C80 C81 H81 . 120.0
C81 C82 C83 . 120.0
C81 C82 H82 . 120.0
C83 C82 H82 . 120.0
C82 C83 C78 . 120.0
C82 C83 H83 . 120.0
C78 C83 H83 . 120.0
C7 N1 C9 . 109.00(19)
C7 N1 B1 . 116.32(19)
C9 N1 B1 . 134.22(19)
C7 N2 C8 . 109.33(19)
C7 N2 C22 . 127.4(2)
C8 N2 C22 . 123.20(19)
C31 N3 C33 . 108.38(19)
C31 N3 B1 . 115.50(18)
C33 N3 B1 . 133.97(18)
C31 N4 C32 . 108.82(18)
C31 N4 C46 . 127.45(19)
C32 N4 C46 . 122.38(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
B1 N1 . 1.590(3)
B1 C1 . 1.607(3)
B1 N3 . 1.608(3)
B1 C55 . 1.651(4)
B2 C31 . 1.595(3)
B2 C7 . 1.609(4)
B2 C56 . 1.705(4)
B2 Cl1 . 1.850(3)
C1 C6 . 1.392(3)
C1 C2 . 1.395(4)
C2 C3 . 1.381(3)
C2 H2 . 0.95
C3 C4 . 1.376(4)
C3 H3 . 0.95
C4 C5 . 1.387(4)
C4 H4 . 0.95
C5 C6 . 1.390(4)
C5 H5 . 0.95
C6 H6 . 0.95
C7 N1 . 1.345(3)
C7 N2 . 1.350(3)
C8 C9 . 1.372(3)
C8 N2 . 1.403(3)
C8 C16 . 1.474(3)
C9 N1 . 1.392(3)
C9 C10 . 1.482(3)
C10 C11 . 1.378(4)
C10 C15 . 1.381(4)
C11 C12 . 1.390(4)
C11 H11 . 0.95
C12 C13 . 1.366(4)
C12 H12 . 0.95
C13 C14 . 1.366(5)
C13 H13 . 0.95
C14 C15 . 1.385(4)
C14 H14 . 0.95
C15 H15 . 0.95
C16 C21 . 1.393(4)
C16 C17 . 1.401(4)
C17 C18 . 1.384(4)
C17 H17 . 0.95
C18 C19 . 1.351(6)
C18 H18 . 0.95
C19 C20 . 1.384(6)
C19 H19 . 0.95
C20 C21 . 1.397(4)
C20 H20 . 0.95
C21 H21 . 0.95
C22 C27 . 1.389(4)
C22 C23 . 1.399(3)
C22 N2 . 1.444(3)
C23 C24 . 1.390(3)
C23 C30 . 1.498(4)
C24 C25 . 1.384(4)
C24 H24 . 0.95
C25 C26 . 1.385(4)
C25 C29 . 1.512(3)
C26 C27 . 1.396(3)
C26 H26 . 0.95
C27 C28 . 1.511(4)
C28 H28A . 0.98
C28 H28B . 0.98
C28 H28C . 0.98
C29 H29A . 0.98
C29 H29B . 0.98
C29 H29C . 0.98
C30 H30A . 0.98
C30 H30B . 0.98
C30 H30C . 0.98
C31 N3 . 1.351(3)
C31 N4 . 1.353(3)
C32 C33 . 1.360(3)
C32 N4 . 1.398(3)
C32 C40 . 1.476(3)
C33 N3 . 1.400(3)
C33 C34 . 1.487(3)
C34 C39 . 1.386(4)
C34 C35 . 1.388(3)
C35 C36 . 1.399(4)
C35 H35 . 0.95
C36 C37 . 1.371(5)
C36 H36 . 0.95
C37 C38 . 1.366(4)
C37 H37 . 0.95
C38 C39 . 1.382(4)
C38 H38 . 0.95
C39 H39 . 0.95
C40 C41 . 1.383(4)
C40 C45 . 1.394(4)
C41 C42 . 1.387(4)
C41 H41 . 0.95
C42 C43 . 1.366(4)
C42 H42 . 0.95
C43 C44 . 1.369(4)
C43 H43 . 0.95
C44 C45 . 1.389(4)
C44 H44 . 0.95
C45 H45 . 0.95
C46 C47 . 1.386(4)
C46 C51 . 1.388(4)
C46 N4 . 1.443(3)
C47 C48 . 1.390(3)
C47 C54 . 1.496(4)
C48 C49 . 1.385(4)
C48 H48 . 0.95
C49 C50 . 1.374(4)
C49 C53 . 1.514(4)
C50 C51 . 1.397(4)
C50 H50 . 0.95
C51 C52 . 1.506(4)
C52 H52A . 0.98
C52 H52B . 0.98
C52 H52C . 0.98
C53 H53A . 0.98
C53 H53B . 0.98
C53 H53C . 0.98
C54 H54A . 0.98
C54 H54B . 0.98
C54 H54C . 0.98
C55 C68 . 1.494(4)
C55 C56 . 1.567(3)
C55 H55 . 1.0
C56 C57 . 1.506(4)
C56 H56 . 1.0
C57 C58 . 1.373(3)
C57 C66 . 1.437(4)
C58 C59 . 1.420(4)
C58 H58 . 0.95
C59 C60 . 1.410(4)
C59 C64 . 1.418(4)
C60 C61 . 1.377(4)
C60 H60 . 0.95
C61 C62 . 1.414(5)
C61 H61 . 0.95
C62 C63 . 1.361(5)
C62 H62 . 0.95
C63 C64 . 1.421(4)
C63 H63 . 0.95
C64 C65 . 1.402(4)
C65 C66 . 1.373(4)
C65 H65 . 0.95
C66 C67 . 1.456(4)
C67 C68 . 1.332(4)
C67 H67 . 0.95
C68 H68 . 0.95
C69 C74 . 1.360(5)
C69 C70 . 1.373(6)
C69 H69 . 0.95
C70 C71 . 1.346(6)
C70 H70 . 0.95
C71 C72 . 1.370(8)
C71 H71 . 0.95
C72 C73 . 1.393(7)
C72 H72 . 0.95
C73 C74 . 1.401(6)
C73 H73 . 0.95
C74 H74 . 0.95
C75 C75 2_656 1.388(18)
C75 C76 . 1.473(12)
C75 H75A . 0.99
C75 H75B . 0.99
C76 C77 . 1.564(11)
C76 H76A . 0.99
C76 H76B . 0.99
C77 H77A . 0.98
C77 H77B . 0.98
C77 H77C . 0.98
C78 C79 . 1.39
C78 C83 . 1.39
C78 H78 . 0.95
C79 C80 . 1.39
C79 H79 . 0.95
C80 C81 . 1.39
C80 H80 . 0.95
C81 C82 . 1.39
C81 H81 . 0.95
C82 C83 . 1.39
C82 H82 . 0.95
C83 H83 . 0.95
