#------------------------------------------------------------------------------
#$Date: 2022-08-19 01:07:58 +0300 (Fri, 19 Aug 2022) $
#$Revision: 277304 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/74/1567493.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_1567493
loop_
_publ_author_name
'Chen, Chaohuang'
'Daniliuc, Constantin Gabriel'
'Klabunde, Sina'
'Hansen, Michael Ryan'
'Kehr, Gerald'
'Erker, Gerhard'
_publ_section_title
;
 Generation of Boryl-nitroxide Radicals from a Boraalkene via the Nitroso
 Ene Reaction
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC02485C
_journal_year                    2022
_chemical_formula_sum            'C39 H38 B F5 N3 O'
_chemical_formula_weight         670.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           'APEX3 v2019.11-0'
_audit_update_record
;
2022-03-11 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.5270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1129(2)
_cell_length_b                   16.9245(3)
_cell_length_c                   15.4437(3)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.3108
_cell_measurement_theta_min      4.0362
_cell_volume                     3431.47(11)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker APEX3 v2019.11-0 Photon III'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker D8 Venture Photon III Diffractometer'
_diffrn_measurement_device_type  'single crystal'
_diffrn_measurement_method       'phi/omega scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            76484
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         3.63
_diffrn_source                   CuK\a
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'micro focus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

SADABS-2016/2 - Bruker AXS area detector scaling and absorption
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M.
& Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         6046
_refine_ls_number_restraints     476
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0568
_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)+(0.0685P)²+3.0810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1534
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4654
_reflns_number_total             6046
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc02485c5.cif
_cod_data_source_block           6_erk10125
_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/rss-feeds/RSC/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        3431.47(10)
_cod_database_code               1567493
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.54777(13) 0.24963(11) 0.73879(12) 0.0264(4) Uani d . . . 1.0 . .
N N3 0.35585(14) 0.21826(11) 0.57610(13) 0.0274(4) Uani d . . . 1.0 . .
O O1 0.33565(13) 0.16146(10) 0.62217(13) 0.0430(5) Uani d . . . 1.0 . .
C C1 0.46582(17) 0.29790(13) 0.71738(15) 0.0270(5) Uani d U . . 1.0 . .
C C2 0.60462(17) 0.25217(14) 0.83366(16) 0.0300(5) Uani d U . . 1.0 . .
H H2 0.665607 0.223898 0.865782 0.036 Uiso calc U . R 1.0 . .
C C3 0.55664(18) 0.30236(14) 0.87114(16) 0.0317(5) Uani d U . . 1.0 . .
H H3 0.577188 0.315959 0.935094 0.038 Uiso calc U . R 1.0 . .
C C11 0.57868(16) 0.20558(14) 0.67326(15) 0.0282(5) Uani d U . . 1.0 . .
C C12 0.59015(18) 0.24797(16) 0.59941(17) 0.0366(6) Uani d U . . 1.0 . .
C C13 0.6255(2) 0.2066(2) 0.54015(19) 0.0510(8) Uani d U . . 1.0 . .
H H13 0.635116 0.233493 0.490013 0.061 Uiso calc U . R 1.0 . .
C C14 0.6469(2) 0.1271(2) 0.5525(2) 0.0588(9) Uani d U . . 1.0 . .
H H14 0.671881 0.100067 0.511408 0.071 Uiso calc U . R 1.0 . .
C C15 0.6324(2) 0.08643(18) 0.62380(18) 0.0471(7) Uani d U . . 1.0 . .
H H15 0.646748 0.031442 0.630668 0.056 Uiso calc U . R 1.0 . .
C C16 0.59701(17) 0.12481(15) 0.68642(16) 0.0316(5) Uani d U . . 1.0 . .
C C17 0.55573(19) 0.33333(16) 0.58015(18) 0.0399(6) Uani d U . . 1.0 . .
H H17 0.576834 0.360877 0.641633 0.048 Uiso calc U . R 1.0 . .
C C18 0.43618(18) 0.33474(14) 0.53700(16) 0.0310(5) Uani d U . . 1.0 . .
H H18 0.412056 0.389259 0.514689 0.037 Uiso calc U . R 1.0 . .
C C19 0.6034(2) 0.3785(2) 0.5205(2) 0.0604(9) Uani d U . . 1.0 . .
H H19A 0.677821 0.375711 0.549649 0.091 Uiso calc U . R 1.0 . .
H H19B 0.581739 0.433871 0.515359 0.091 Uiso calc U . R 1.0 . .
H H19C 0.58126 0.354841 0.458306 0.091 Uiso calc U . R 1.0 . .
C C20 0.57577(18) 0.07651(14) 0.76043(16) 0.0327(5) Uani d U . . 1.0 . .
H H20 0.540432 0.111603 0.791132 0.039 Uiso calc U . R 1.0 . .
C C21 0.5046(2) 0.00764(16) 0.7159(2) 0.0461(7) Uani d U . . 1.0 . .
H H21A 0.443592 0.027606 0.666139 0.069 Uiso calc U . R 1.0 . .
H H21B 0.484905 -0.018885 0.763111 0.069 Uiso calc U . R 1.0 . .
H H21C 0.539728 -0.029995 0.689746 0.069 Uiso calc U . R 1.0 . .
C C22 0.6745(2) 0.04689(16) 0.83570(18) 0.0401(6) Uani d U . . 1.0 . .
H H22A 0.711082 0.012772 0.807175 0.06 Uiso calc U . R 1.0 . .
H H22B 0.658063 0.016864 0.882598 0.06 Uiso calc U . R 1.0 . .
H H22C 0.717513 0.092138 0.865398 0.06 Uiso calc U . R 1.0 . .
N N2 0.47182(14) 0.33062(11) 0.79954(13) 0.0296(4) Uani d . . . 1.0 . .
C C31 0.40494(17) 0.39073(14) 0.81373(15) 0.0293(5) Uani d U . . 1.0 . .
C C32 0.31286(18) 0.36715(14) 0.82084(15) 0.0314(5) Uani d U . . 1.0 . .
C C33 0.24925(19) 0.42699(16) 0.82988(16) 0.0355(6) Uani d U . . 1.0 . .
H H33 0.185475 0.413576 0.833567 0.043 Uiso calc U . R 1.0 . .
C C34 0.2775(2) 0.50571(16) 0.83358(18) 0.0427(6) Uani d U . . 1.0 . .
H H34 0.231803 0.545686 0.837205 0.051 Uiso calc U . R 1.0 . .
C C35 0.3713(2) 0.52643(16) 0.83203(19) 0.0434(6) Uani d U . . 1.0 . .
H H35 0.390742 0.580497 0.837553 0.052 Uiso calc U . R 1.0 . .
C C37 0.2875(2) 0.28128(16) 0.8272(2) 0.0449(7) Uani d U . . 1.0 . .
H H37 0.315313 0.249803 0.787096 0.054 Uiso calc U . R 1.0 . .
C C38 0.1740(2) 0.26355(19) 0.7976(2) 0.0544(8) Uani d U . . 1.0 . .
H H38A 0.164275 0.206795 0.803803 0.082 Uiso calc U . R 1.0 . .
H H38B 0.145957 0.292989 0.837322 0.082 Uiso calc U . R 1.0 . .
H H38C 0.138962 0.279456 0.732592 0.082 Uiso calc U . R 1.0 . .
C C39 0.3423(2) 0.25510(19) 0.9293(3) 0.0645(10) Uani d U . . 1.0 . .
H H39A 0.32721 0.199351 0.935648 0.097 Uiso calc U . R 1.0 . .
H H39B 0.415924 0.261991 0.947005 0.097 Uiso calc U . R 1.0 . .
H H39C 0.318396 0.287331 0.969918 0.097 Uiso calc U . R 1.0 . .
C C36 0.4384(2) 0.46944(14) 0.82249(17) 0.0357(6) Uani d U . . 1.0 . .
C C40 0.5453(2) 0.49368(16) 0.8295(2) 0.0428(6) Uani d U . . 1.0 . .
H H40 0.574093 0.450479 0.802325 0.051 Uiso calc U . R 1.0 . .
C C41 0.6128(2) 0.50320(17) 0.9318(2) 0.0496(7) Uani d U . . 1.0 . .
H H41A 0.584539 0.544378 0.959943 0.074 Uiso calc U . R 1.0 . .
H H41B 0.68168 0.518247 0.936849 0.074 Uiso calc U . R 1.0 . .
H H41C 0.615553 0.453089 0.964466 0.074 Uiso calc U . R 1.0 . .
C C42 0.5500(3) 0.5713(2) 0.7796(3) 0.0673(10) Uani d U . . 1.0 . .
H H42A 0.504632 0.56783 0.714112 0.101 Uiso calc U . R 1.0 . .
H H42B 0.61995 0.580526 0.78335 0.101 Uiso calc U . R 1.0 . .
H H42C 0.528333 0.615185 0.809459 0.101 Uiso calc U . R 1.0 . .
B B1 0.38374(19) 0.30501(16) 0.61082(17) 0.0269(5) Uani d . . D 1.0 . .
C C51 0.2867(2) 0.36231(19) 0.6006(2) 0.0254(7) Uani d U P D 0.871(3) A 1
C C52 0.1875(2) 0.33877(17) 0.58432(17) 0.0289(6) Uani d U P D 0.871(3) A 1
F F52 0.16170(13) 0.26140(14) 0.57398(12) 0.0362(5) Uani d U P D 0.871(3) A 1
C C53 0.1104(3) 0.3908(2) 0.5798(2) 0.0430(9) Uani d U P D 0.871(3) A 1
F F53 0.01683(14) 0.36391(14) 0.56824(13) 0.0571(6) Uani d U P D 0.871(3) A 1
C C54 0.1306(3) 0.4705(3) 0.5908(2) 0.0473(10) Uani d U P D 0.871(3) A 1
F F54 0.05770(18) 0.52197(13) 0.59079(13) 0.0680(7) Uani d U P D 0.871(3) A 1
C C55 0.2264(3) 0.49721(17) 0.60366(19) 0.0439(8) Uani d U P D 0.871(3) A 1
F F55 0.2472(2) 0.57498(10) 0.61343(14) 0.0661(7) Uani d U P D 0.871(3) A 1
C C56 0.2992(4) 0.4435(3) 0.6077(4) 0.0340(12) Uani d U P D 0.871(3) A 1
F F56 0.39462(18) 0.47358(10) 0.62349(12) 0.0432(5) Uani d U P D 0.871(3) A 1
C C51A 0.2648(11) 0.3329(10) 0.5998(17) 0.029(6) Uani d U P D 0.129(3) A 2
C C52A 0.1837(12) 0.2880(10) 0.6004(19) 0.036(6) Uani d U P D 0.129(3) A 2
F F52A 0.1880(9) 0.2074(8) 0.6103(9) 0.048(3) Uani d U P D 0.129(3) A 2
C C53A 0.0895(11) 0.3156(9) 0.5932(16) 0.049(6) Uani d U P D 0.129(3) A 2
F F53A 0.0135(9) 0.2688(11) 0.5961(10) 0.076(5) Uani d U P D 0.129(3) A 2
C C54A 0.0748(15) 0.3959(10) 0.586(2) 0.049(7) Uani d U P D 0.129(3) A 2
F F54A -0.0166(11) 0.4274(12) 0.5808(11) 0.088(6) Uani d U P D 0.129(3) A 2
C C55A 0.1512(15) 0.4462(11) 0.585(3) 0.060(8) Uani d U P D 0.129(3) A 2
F F55A 0.1394(16) 0.5250(11) 0.5810(12) 0.091(6) Uani d U P D 0.129(3) A 2
C C56A 0.2445(13) 0.4130(10) 0.5957(15) 0.038(5) Uani d U P D 0.129(3) A 2
F F56A 0.3198(17) 0.4619(12) 0.5955(16) 0.038(5) Uani d U P D 0.129(3) A 2
C C61 0.35427(17) 0.20878(14) 0.48642(16) 0.0291(5) Uani d U . . 1.0 . .
C C62 0.39233(18) 0.27630(15) 0.45779(16) 0.0325(5) Uani d U . . 1.0 . .
C C63 0.3873(2) 0.27912(19) 0.36641(18) 0.0465(7) Uani d U . . 1.0 . .
H H63 0.410914 0.324444 0.344115 0.056 Uiso calc U . R 1.0 . .
C C64 0.3471(2) 0.2146(2) 0.3071(2) 0.0582(9) Uani d U . . 1.0 . .
H H64 0.342359 0.216957 0.244158 0.07 Uiso calc U . R 1.0 . .
C C65 0.3144(2) 0.1481(2) 0.3392(2) 0.0561(8) Uani d U . . 1.0 . .
H H65 0.288959 0.104547 0.298411 0.067 Uiso calc U . R 1.0 . .
C C66 0.3180(2) 0.14351(16) 0.42914(19) 0.0431(6) Uani d U . . 1.0 . .
H H66 0.296367 0.097244 0.45148 0.052 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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C1 N1 C2 . . 110.48(18) ?
C1 N1 C11 . . 126.13(18) ?
C2 N1 C11 . . 123.22(18) ?
O1 N3 C61 . . 122.7(2) ?
O1 N3 B1 . . 126.17(19) ?
C61 N3 B1 . . 111.17(18) ?
N1 C1 N2 . . 105.25(18) ?
N1 C1 B1 . . 121.14(19) ?
N2 C1 B1 . . 133.6(2) ?
C3 C2 N1 . . 106.67(19) ?
C3 C2 H2 . . 126.7 ?
N1 C2 H2 . . 126.7 ?
C2 C3 N2 . . 107.4(2) ?
C2 C3 H3 . . 126.3 ?
N2 C3 H3 . . 126.3 ?
C16 C11 C12 . . 123.3(2) ?
C16 C11 N1 . . 119.4(2) ?
C12 C11 N1 . . 117.3(2) ?
C13 C12 C11 . . 117.1(3) ?
C13 C12 C17 . . 121.3(2) ?
C11 C12 C17 . . 121.4(2) ?
C14 C13 C12 . . 121.1(3) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C15 C14 C13 . . 120.7(3) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C14 C15 C16 . . 121.0(3) ?
C14 C15 H15 . . 119.5 ?
C16 C15 H15 . . 119.5 ?
C11 C16 C15 . . 116.7(2) ?
C11 C16 C20 . . 124.0(2) ?
C15 C16 C20 . . 119.2(2) ?
C12 C17 C19 . . 114.4(2) ?
C12 C17 C18 . . 108.3(2) ?
C19 C17 C18 . . 112.2(2) ?
C12 C17 H17 . . 107.2 ?
C19 C17 H17 . . 107.2 ?
C18 C17 H17 . . 107.2 ?
C62 C18 C17 . . 112.9(2) ?
C62 C18 B1 . . 101.81(18) ?
C17 C18 B1 . . 112.75(18) ?
C62 C18 H18 . . 109.7 ?
C17 C18 H18 . . 109.7 ?
B1 C18 H18 . . 109.7 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C16 C20 C21 . . 110.5(2) ?
C16 C20 C22 . . 111.7(2) ?
C21 C20 C22 . . 110.9(2) ?
C16 C20 H20 . . 107.9 ?
C21 C20 H20 . . 107.9 ?
C22 C20 H20 . . 107.9 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C1 N2 C3 . . 110.16(19) ?
C1 N2 C31 . . 127.08(18) ?
C3 N2 C31 . . 122.64(18) ?
C32 C31 C36 . . 123.5(2) ?
C32 C31 N2 . . 118.9(2) ?
C36 C31 N2 . . 117.6(2) ?
C33 C32 C31 . . 116.8(2) ?
C33 C32 C37 . . 121.1(2) ?
C31 C32 C37 . . 121.9(2) ?
C34 C33 C32 . . 121.1(2) ?
C34 C33 H33 . . 119.4 ?
C32 C33 H33 . . 119.4 ?
C35 C34 C33 . . 120.5(2) ?
C35 C34 H34 . . 119.8 ?
C33 C34 H34 . . 119.8 ?
C34 C35 C36 . . 121.3(3) ?
C34 C35 H35 . . 119.4 ?
C36 C35 H35 . . 119.4 ?
C32 C37 C38 . . 114.7(2) ?
C32 C37 C39 . . 107.5(2) ?
C38 C37 C39 . . 109.1(2) ?
C32 C37 H37 . . 108.5 ?
C38 C37 H37 . . 108.5 ?
C39 C37 H37 . . 108.5 ?
C37 C38 H38A . . 109.5 ?
C37 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C37 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C37 C39 H39A . . 109.5 ?
C37 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C37 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C35 C36 C31 . . 116.7(2) ?
C35 C36 C40 . . 119.8(2) ?
C31 C36 C40 . . 123.4(2) ?
C41 C40 C36 . . 109.0(2) ?
C41 C40 C42 . . 107.7(2) ?
C36 C40 C42 . . 114.6(2) ?
C41 C40 H40 . . 108.4 ?
C36 C40 H40 . . 108.4 ?
C42 C40 H40 . . 108.4 ?
C40 C41 H41A . . 109.5 ?
C40 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C40 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
C40 C42 H42A . . 109.5 ?
C40 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C40 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
N3 B1 C1 . . 105.83(18) ?
N3 B1 C51 . . 115.3(2) ?
C1 B1 C51 . . 113.5(2) ?
N3 B1 C18 . . 99.78(18) ?
C1 B1 C18 . . 112.76(19) ?
C51 B1 C18 . . 108.9(2) ?
N3 B1 C51A . . 96.5(6) ?
C1 B1 C51A . . 115.6(9) ?
C18 B1 C51A . . 121.7(8) ?
C56 C51 C52 . . 113.0(3) ?
C56 C51 B1 . . 120.1(3) ?
C52 C51 B1 . . 126.9(3) ?
F52 C52 C53 . . 116.0(3) ?
F52 C52 C51 . . 120.6(2) ?
C53 C52 C51 . . 123.3(3) ?
F53 C53 C54 . . 119.8(3) ?
F53 C53 C52 . . 120.5(3) ?
C54 C53 C52 . . 119.7(3) ?
F54 C54 C55 . . 120.0(4) ?
F54 C54 C53 . . 120.6(4) ?
C55 C54 C53 . . 119.4(4) ?
F55 C55 C56 . . 121.3(4) ?
F55 C55 C54 . . 120.2(3) ?
C56 C55 C54 . . 118.4(4) ?
C55 C56 F56 . . 115.8(4) ?
C55 C56 C51 . . 126.1(5) ?
F56 C56 C51 . . 118.0(4) ?
C52A C51A C56A . . 112.5(13) ?
C52A C51A B1 . . 129.9(12) ?
C56A C51A B1 . . 117.4(11) ?
F52A C52A C53A . . 110.5(12) ?
F52A C52A C51A . . 123.1(13) ?
C53A C52A C51A . . 126.4(14) ?
F53A C53A C54A . . 119.2(13) ?
F53A C53A C52A . . 123.7(13) ?
C54A C53A C52A . . 117.0(13) ?
C53A C54A F54A . . 119.9(15) ?
C53A C54A C55A . . 121.3(13) ?
F54A C54A C55A . . 118.8(14) ?
F55A C55A C54A . . 122.2(16) ?
F55A C55A C56A . . 120.3(15) ?
C54A C55A C56A . . 117.4(15) ?
F56A C56A C51A . . 116.9(15) ?
F56A C56A C55A . . 117.8(17) ?
C51A C56A C55A . . 125.1(15) ?
N3 C61 C66 . . 126.5(2) ?
N3 C61 C62 . . 110.7(2) ?
C66 C61 C62 . . 122.8(2) ?
C63 C62 C61 . . 117.8(2) ?
C63 C62 C18 . . 130.6(2) ?
C61 C62 C18 . . 111.6(2) ?
C62 C63 C64 . . 119.7(3) ?
C62 C63 H63 . . 120.2 ?
C64 C63 H63 . . 120.2 ?
C65 C64 C63 . . 120.6(3) ?
C65 C64 H64 . . 119.7 ?
C63 C64 H64 . . 119.7 ?
C66 C65 C64 . . 121.2(3) ?
C66 C65 H65 . . 119.4 ?
C64 C65 H65 . . 119.4 ?
C65 C66 C61 . . 117.8(3) ?
C65 C66 H66 . . 121.1 ?
C61 C66 H66 . . 121.1 ?
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 C1 . 1.354(3) ?
N1 C2 . 1.389(3) ?
N1 C11 . 1.447(3) ?
N3 O1 . 1.289(2) ?
N3 C61 . 1.386(3) ?
N3 B1 . 1.563(3) ?
C1 N2 . 1.358(3) ?
C1 B1 . 1.633(3) ?
C2 C3 . 1.343(3) ?
C2 H2 . 0.95 ?
C3 N2 . 1.383(3) ?
C3 H3 . 0.95 ?
C11 C16 . 1.392(3) ?
C11 C12 . 1.406(3) ?
C12 C13 . 1.382(4) ?
C12 C17 . 1.518(4) ?
C13 C14 . 1.377(5) ?
C13 H13 . 0.95 ?
C14 C15 . 1.375(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.401(3) ?
C15 H15 . 0.95 ?
C16 C20 . 1.522(3) ?
C17 C19 . 1.530(4) ?
C17 C18 . 1.570(3) ?
C17 H17 . 1.0 ?
C18 C62 . 1.517(3) ?
C18 B1 . 1.649(3) ?
C18 H18 . 1.0 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 C21 . 1.528(4) ?
C20 C22 . 1.535(3) ?
C20 H20 . 1.0 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
N2 C31 . 1.458(3) ?
C31 C32 . 1.402(3) ?
C31 C36 . 1.403(3) ?
C32 C33 . 1.394(3) ?
C32 C37 . 1.508(4) ?
C33 C34 . 1.386(4) ?
C33 H33 . 0.95 ?
C34 C35 . 1.379(4) ?
C34 H34 . 0.95 ?
C35 C36 . 1.397(4) ?
C35 H35 . 0.95 ?
C37 C38 . 1.525(4) ?
C37 C39 . 1.544(4) ?
C37 H37 . 1.0 ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C36 C40 . 1.529(4) ?
C40 C41 . 1.526(4) ?
C40 C42 . 1.537(4) ?
C40 H40 . 1.0 ?
C41 H41A . 0.98 ?
C41 H41B . 0.98 ?
C41 H41C . 0.98 ?
C42 H42A . 0.98 ?
C42 H42B . 0.98 ?
C42 H42C . 0.98 ?
B1 C51 . 1.638(4) ?
B1 C51A . 1.691(14) ?
C51 C56 . 1.384(6) ?
C51 C52 . 1.387(4) ?
C52 F52 . 1.353(3) ?
C52 C53 . 1.381(4) ?
C53 F53 . 1.345(4) ?
C53 C54 . 1.376(5) ?
C54 F54 . 1.348(4) ?
C54 C55 . 1.368(5) ?
C55 F55 . 1.345(4) ?
C55 C56 . 1.356(6) ?
C56 F56 . 1.376(5) ?
C51A C52A . 1.377(13) ?
C51A C56A . 1.381(16) ?
C52A F52A . 1.372(14) ?
C52A C53A . 1.374(13) ?
C53A F53A . 1.348(13) ?
C53A C54A . 1.372(13) ?
C54A F54A . 1.373(13) ?
C54A C55A . 1.375(13) ?
C55A F55A . 1.343(13) ?
C55A C56A . 1.386(13) ?
C56A F56A . 1.348(13) ?
C61 C66 . 1.390(4) ?
C61 C62 . 1.401(3) ?
C62 C63 . 1.387(3) ?
C63 C64 . 1.404(5) ?
C63 H63 . 0.95 ?
C64 C65 . 1.376(5) ?
C64 H64 . 0.95 ?
C65 C66 . 1.374(4) ?
C65 H65 . 0.95 ?
C66 H66 . 0.95 ?
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
C2 N1 C1 N2 . . . . 0.0(2) ?
C11 N1 C1 N2 . . . . -175.4(2) ?
C2 N1 C1 B1 . . . . -178.5(2) ?
C11 N1 C1 B1 . . . . 6.1(3) ?
C1 N1 C2 C3 . . . . 0.3(3) ?
C11 N1 C2 C3 . . . . 175.9(2) ?
N1 C2 C3 N2 . . . . -0.5(3) ?
C1 N1 C11 C16 . . . . -128.2(2) ?
C2 N1 C11 C16 . . . . 57.0(3) ?
C1 N1 C11 C12 . . . . 52.8(3) ?
C2 N1 C11 C12 . . . . -122.1(2) ?
C16 C11 C12 C13 . . . . -2.7(4) ?
N1 C11 C12 C13 . . . . 176.3(2) ?
C16 C11 C12 C17 . . . . 171.6(2) ?
N1 C11 C12 C17 . . . . -9.4(3) ?
C11 C12 C13 C14 . . . . 0.9(4) ?
C17 C12 C13 C14 . . . . -173.4(3) ?
C12 C13 C14 C15 . . . . 0.8(5) ?
C13 C14 C15 C16 . . . . -0.9(5) ?
C12 C11 C16 C15 . . . . 2.6(3) ?
N1 C11 C16 C15 . . . . -176.4(2) ?
C12 C11 C16 C20 . . . . -174.1(2) ?
N1 C11 C16 C20 . . . . 6.9(3) ?
C14 C15 C16 C11 . . . . -0.8(4) ?
C14 C15 C16 C20 . . . . 176.2(3) ?
C13 C12 C17 C19 . . . . -25.0(4) ?
C11 C12 C17 C19 . . . . 161.0(2) ?
C13 C12 C17 C18 . . . . 101.1(3) ?
C11 C12 C17 C18 . . . . -73.0(3) ?
C12 C17 C18 C62 . . . . -48.6(3) ?
C19 C17 C18 C62 . . . . 78.7(3) ?
C12 C17 C18 B1 . . . . 66.1(3) ?
C19 C17 C18 B1 . . . . -166.6(2) ?
C11 C16 C20 C21 . . . . 123.8(2) ?
C15 C16 C20 C21 . . . . -52.9(3) ?
C11 C16 C20 C22 . . . . -112.3(3) ?
C15 C16 C20 C22 . . . . 71.0(3) ?
N1 C1 N2 C3 . . . . -0.3(3) ?
B1 C1 N2 C3 . . . . 177.9(2) ?
N1 C1 N2 C31 . . . . 175.9(2) ?
B1 C1 N2 C31 . . . . -5.9(4) ?
C2 C3 N2 C1 . . . . 0.5(3) ?
C2 C3 N2 C31 . . . . -175.9(2) ?
C1 N2 C31 C32 . . . . 83.8(3) ?
C3 N2 C31 C32 . . . . -100.5(3) ?
C1 N2 C31 C36 . . . . -98.2(3) ?
C3 N2 C31 C36 . . . . 77.6(3) ?
C36 C31 C32 C33 . . . . 5.1(3) ?
N2 C31 C32 C33 . . . . -177.01(19) ?
C36 C31 C32 C37 . . . . -169.5(2) ?
N2 C31 C32 C37 . . . . 8.4(3) ?
C31 C32 C33 C34 . . . . -1.3(3) ?
C37 C32 C33 C34 . . . . 173.3(2) ?
C32 C33 C34 C35 . . . . -2.6(4) ?
C33 C34 C35 C36 . . . . 2.9(4) ?
C33 C32 C37 C38 . . . . 28.0(4) ?
C31 C32 C37 C38 . . . . -157.6(2) ?
C33 C32 C37 C39 . . . . -93.5(3) ?
C31 C32 C37 C39 . . . . 80.9(3) ?
C34 C35 C36 C31 . . . . 0.6(4) ?
C34 C35 C36 C40 . . . . -174.7(2) ?
C32 C31 C36 C35 . . . . -4.7(3) ?
N2 C31 C36 C35 . . . . 177.3(2) ?
C32 C31 C36 C40 . . . . 170.4(2) ?
N2 C31 C36 C40 . . . . -7.5(3) ?
C35 C36 C40 C41 . . . . 79.1(3) ?
C31 C36 C40 C41 . . . . -95.9(3) ?
C35 C36 C40 C42 . . . . -41.6(4) ?
C31 C36 C40 C42 . . . . 143.3(3) ?
O1 N3 B1 C1 . . . . 44.5(3) ?
C61 N3 B1 C1 . . . . -136.00(18) ?
O1 N3 B1 C51 . . . . -81.8(3) ?
C61 N3 B1 C51 . . . . 97.6(2) ?
O1 N3 B1 C18 . . . . 161.72(19) ?
C61 N3 B1 C18 . . . . -18.8(2) ?
O1 N3 B1 C51A . . . . -74.5(9) ?
C61 N3 B1 C51A . . . . 105.0(8) ?
N1 C1 B1 N3 . . . . 49.1(3) ?
N2 C1 B1 N3 . . . . -128.8(3) ?
N1 C1 B1 C51 . . . . 176.5(2) ?
N2 C1 B1 C51 . . . . -1.4(4) ?
N1 C1 B1 C18 . . . . -59.0(3) ?
N2 C1 B1 C18 . . . . 123.1(3) ?
N1 C1 B1 C51A . . . . 154.5(6) ?
N2 C1 B1 C51A . . . . -23.4(7) ?
C62 C18 B1 N3 . . . . 21.0(2) ?
C17 C18 B1 N3 . . . . -100.3(2) ?
C62 C18 B1 C1 . . . . 132.9(2) ?
C17 C18 B1 C1 . . . . 11.6(3) ?
C62 C18 B1 C51 . . . . -100.1(2) ?
C17 C18 B1 C51 . . . . 138.6(2) ?
C62 C18 B1 C51A . . . . -82.9(8) ?
C17 C18 B1 C51A . . . . 155.8(8) ?
N3 B1 C51 C56 . . . . -164.5(3) ?
C1 B1 C51 C56 . . . . 73.2(4) ?
C18 B1 C51 C56 . . . . -53.4(4) ?
N3 B1 C51 C52 . . . . 15.0(4) ?
C1 B1 C51 C52 . . . . -107.3(3) ?
C18 B1 C51 C52 . . . . 126.2(3) ?
C56 C51 C52 F52 . . . . 178.9(3) ?
B1 C51 C52 F52 . . . . -0.7(4) ?
C56 C51 C52 C53 . . . . -2.7(5) ?
B1 C51 C52 C53 . . . . 177.7(3) ?
F52 C52 C53 F53 . . . . 1.7(4) ?
C51 C52 C53 F53 . . . . -176.8(3) ?
F52 C52 C53 C54 . . . . 179.2(3) ?
C51 C52 C53 C54 . . . . 0.8(5) ?
F53 C53 C54 F54 . . . . 0.6(5) ?
C52 C53 C54 F54 . . . . -177.0(3) ?
F53 C53 C54 C55 . . . . 179.2(3) ?
C52 C53 C54 C55 . . . . 1.6(5) ?
F54 C54 C55 F55 . . . . -2.1(5) ?
C53 C54 C55 F55 . . . . 179.2(3) ?
F54 C54 C55 C56 . . . . 176.9(3) ?
C53 C54 C55 C56 . . . . -1.8(5) ?
F55 C55 C56 F56 . . . . 0.8(6) ?
C54 C55 C56 F56 . . . . -178.2(3) ?
F55 C55 C56 C51 . . . . 178.5(4) ?
C54 C55 C56 C51 . . . . -0.5(7) ?
C52 C51 C56 C55 . . . . 2.6(6) ?
B1 C51 C56 C55 . . . . -177.7(4) ?
C52 C51 C56 F56 . . . . -179.7(3) ?
B1 C51 C56 F56 . . . . -0.1(6) ?
N3 B1 C51A C52A . . . . 24.(3) ?
C1 B1 C51A C52A . . . . -87.(3) ?
C18 B1 C51A C52A . . . . 130.(2) ?
N3 B1 C51A C56A . . . . -160.5(19) ?
C1 B1 C51A C56A . . . . 88.(2) ?
C18 B1 C51A C56A . . . . -55.(2) ?
C56A C51A C52A F52A . . . . -176.(2) ?
B1 C51A C52A F52A . . . . 0.(4) ?
C56A C51A C52A C53A . . . . 3.(4) ?
B1 C51A C52A C53A . . . . 178.(2) ?
F52A C52A C53A F53A . . . . 0.(3) ?
C51A C52A C53A F53A . . . . -179.(2) ?
F52A C52A C53A C54A . . . . 178.(2) ?
C51A C52A C53A C54A . . . . -1.(4) ?
F53A C53A C54A F54A . . . . 0.(4) ?
C52A C53A C54A F54A . . . . -178.(2) ?
F53A C53A C54A C55A . . . . 178.(3) ?
C52A C53A C54A C55A . . . . 0.(5) ?
C53A C54A C55A F55A . . . . -178.(3) ?
F54A C54A C55A F55A . . . . 0.(5) ?
C53A C54A C55A C56A . . . . -2.(5) ?
F54A C54A C55A C56A . . . . 176.(3) ?
C52A C51A C56A F56A . . . . 180.(2) ?
B1 C51A C56A F56A . . . . 4.(3) ?
C52A C51A C56A C55A . . . . -5.(4) ?
B1 C51A C56A C55A . . . . 179.(2) ?
F55A C55A C56A F56A . . . . -4.(5) ?
C54A C55A C56A F56A . . . . 180.(3) ?
F55A C55A C56A C51A . . . . -179.(3) ?
C54A C55A C56A C51A . . . . 5.(5) ?
O1 N3 C61 C66 . . . . 9.8(3) ?
B1 N3 C61 C66 . . . . -169.7(2) ?
O1 N3 C61 C62 . . . . -171.96(19) ?
B1 N3 C61 C62 . . . . 8.5(2) ?
N3 C61 C62 C63 . . . . -174.3(2) ?
C66 C61 C62 C63 . . . . 4.0(4) ?
N3 C61 C62 C18 . . . . 7.3(3) ?
C66 C61 C62 C18 . . . . -174.4(2) ?
C17 C18 C62 C63 . . . . -75.5(3) ?
B1 C18 C62 C63 . . . . 163.3(3) ?
C17 C18 C62 C61 . . . . 102.6(2) ?
B1 C18 C62 C61 . . . . -18.5(2) ?
C61 C62 C63 C64 . . . . -1.4(4) ?
C18 C62 C63 C64 . . . . 176.6(2) ?
C62 C63 C64 C65 . . . . -1.2(4) ?
C63 C64 C65 C66 . . . . 1.5(5) ?
C64 C65 C66 C61 . . . . 0.9(4) ?
N3 C61 C66 C65 . . . . 174.2(2) ?
C62 C61 C66 C65 . . . . -3.8(4) ?
