#------------------------------------------------------------------------------
#$Date: 2020-08-05 01:49:23 +0300 (Wed, 05 Aug 2020) $
#$Revision: 254806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/51/4135141.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_4135141
loop_
_publ_author_name
'Karimi, Mohammadjavad'
'Borthakur, Rosmita'
'Dorsey, Christopher L.'
'Chen, Chang-Hong'
'Lajeune, Sébastien'
'Gabbai, Francois P.'
_publ_section_title
;
 Bifunctional carbenium dications as metal-free catalysts for the
 reduction of oxygen.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c04841
_journal_year                    2020
_chemical_formula_moiety         'C38 H22 B2 F8 O2, 2(C2 H3 N)'
_chemical_formula_sum            'C42 H28 B2 F8 N2 O2'
_chemical_formula_weight         766.28
_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     direct
_audit_creation_date             2020-04-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                105.814(3)
_cell_angle_beta                 97.712(3)
_cell_angle_gamma                90.105(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4600(3)
_cell_length_b                   13.8649(4)
_cell_length_c                   15.5724(5)
_cell_measurement_reflns_used    39817
_cell_measurement_temperature    163
_cell_measurement_theta_max      30.1030
_cell_measurement_theta_min      1.6610
_cell_volume                     1740.15(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      163
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -78.29 144.71   1.00    6.00    --  -30.53  73.80 -99.74  223
  2  ω    -78.29 144.71   1.00    6.00    --  -30.53  73.80  67.79  223
  3  ω    -78.29 144.71   1.00    6.00    --  -30.53  73.80 156.90  223
  4  ω    -77.20 145.80   1.00    6.00    --  -29.45  73.80  -6.36  223
  5  ω    -78.29 144.71   1.00    6.00    --  -30.53  73.80-154.80  223
  6  ω    -78.29 144.71   1.00    6.00    --  -30.53  73.80 -55.38  223
  7  ω    -78.29 144.71   1.00    6.00    --  -30.53  73.80 112.30  223
  8  ω    -51.27 171.73   1.00    6.00    --   -3.52  73.80-137.93  223
  9  ω    -78.29 144.71   1.00    6.00    --  -30.53  73.80   0.28  223
 10  ω    -78.29 144.71   1.00    6.00    --  -30.53  73.80-105.67  223
 11  ω    -78.29 144.71   1.00    6.00    --  -30.53  73.80 164.49  223
 12  ω    -78.29 144.71   1.00    6.00    --  -30.53  73.80  48.26  223
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0777515000
_diffrn_orient_matrix_UB_12      0.0140786000
_diffrn_orient_matrix_UB_13      -0.0139318000
_diffrn_orient_matrix_UB_21      0.0320710000
_diffrn_orient_matrix_UB_22      0.0263233000
_diffrn_orient_matrix_UB_23      -0.0273296000
_diffrn_orient_matrix_UB_31      -0.0098117000
_diffrn_orient_matrix_UB_32      -0.0440509000
_diffrn_orient_matrix_UB_33      -0.0366767000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            80086
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.114
_diffrn_reflns_theta_min         1.750
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear greenish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         9711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0789
_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)+(0.0290P)²+4.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9556
_reflns_number_total             9711
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c04841_si_002.cif
_cod_data_source_block           mo_chc05242016
_cod_original_cell_volume        1740.14(10)
_cod_database_code               4135141
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H10OBF4N
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.891
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(F9)=Sof(F10)=Sof(F11)=1-FVAR(1)
 Sof(F2)=Sof(F3)=Sof(F4)=FVAR(1)
 Sof(F12)=Sof(F13)=1-FVAR(2)
 Sof(F7)=Sof(F8)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C29(H29), C30(H30),
  C31(H31), C34(H34), C35(H35), C36(H36), C37(H37)
3.b Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C39(H39A,H39B,H39C)
;
_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.655
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.1640(3) 0.80103(18) 0.05664(16) 0.0196(4) Uani 1 1 d . . . . .
F1 F 0.30312(18) 0.78065(13) 0.01844(11) 0.0400(4) Uani 1 1 d . . . . .
F2 F 0.1853(5) 0.7661(2) 0.13402(16) 0.0362(7) Uani 0.780(10) 1 d . . P . .
F3 F 0.1362(6) 0.9011(4) 0.0810(4) 0.0412(10) Uani 0.780(10) 1 d . . P . .
F4 F 0.0373(3) 0.7480(3) -0.00154(18) 0.0414(9) Uani 0.780(10) 1 d . . P . .
F9 F 0.094(2) 0.7501(7) 0.1020(11) 0.050(5) Uani 0.220(10) 1 d . . P . .
F10 F 0.189(2) 0.9054(14) 0.1053(12) 0.043(4) Uani 0.220(10) 1 d . . P . .
F11 F 0.0559(11) 0.8047(12) -0.0223(6) 0.051(4) Uani 0.220(10) 1 d . . P . .
F5 F 1.12520(17) 0.79110(11) 0.52125(9) 0.0277(3) Uani 1 1 d . . . . .
F6 F 1.30904(17) 0.80301(11) 0.64434(10) 0.0324(3) Uani 1 1 d . . . . .
F7 F 1.222(2) 0.6497(14) 0.5554(12) 0.037(2) Uani 0.55(9) 1 d . . P . .
F8 F 1.0574(15) 0.7496(9) 0.6401(9) 0.029(3) Uani 0.55(9) 1 d . . P . .
F12 F 1.244(4) 0.6534(19) 0.540(3) 0.046(5) Uani 0.45(9) 1 d . . P . .
F13 F 1.061(2) 0.724(5) 0.632(2) 0.062(5) Uani 0.45(9) 1 d . . P . .
B4 B 1.1821(3) 0.74505(18) 0.58822(16) 0.0198(4) Uani 1 1 d . . . . .
O2 O 0.48433(18) 0.94143(11) 0.24821(10) 0.0213(3) Uani 1 1 d . . . . .
O3 O 0.76041(18) 0.86510(11) 0.48729(10) 0.0198(3) Uani 1 1 d . . . . .
C1 C 0.6678(2) 0.66769(14) 0.10029(13) 0.0140(3) Uani 1 1 d . . . . .
C2 C 0.6161(2) 0.63564(15) 0.00517(13) 0.0168(4) Uani 1 1 d . . . . .
H2 H 0.544364 0.675701 -0.021101 0.020 Uiso 1 1 calc R U . . .
C3 C 0.6665(2) 0.54863(15) -0.04980(13) 0.0180(4) Uani 1 1 d . . . . .
H3 H 0.626859 0.530176 -0.112334 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7757(2) 0.48600(15) -0.01577(13) 0.0173(4) Uani 1 1 d . . . . .
H4 H 0.811666 0.426522 -0.053463 0.021 Uiso 1 1 calc R U . . .
C5 C 1.0399(2) 0.43585(15) 0.18148(14) 0.0179(4) Uani 1 1 d . . . . .
H5 H 1.076298 0.378606 0.140986 0.021 Uiso 1 1 calc R U . . .
C6 C 1.0950(3) 0.46330(16) 0.27551(14) 0.0201(4) Uani 1 1 d . . . . .
H6 H 1.172080 0.423659 0.298590 0.024 Uiso 1 1 calc R U . . .
C7 C 1.0403(2) 0.54556(16) 0.33438(14) 0.0188(4) Uani 1 1 d . . . . .
H7 H 1.078408 0.559779 0.396931 0.023 Uiso 1 1 calc R U . . .
C8 C 0.9280(2) 0.60992(14) 0.30393(13) 0.0138(3) Uani 1 1 d . . . . .
C9 C 0.7710(2) 0.60514(14) 0.13299(12) 0.0137(3) Uani 1 1 d . . . . .
C10 C 0.8256(2) 0.51706(14) 0.07502(13) 0.0147(3) Uani 1 1 d . . . . .
C11 C 0.9310(2) 0.49733(14) 0.15320(13) 0.0146(3) Uani 1 1 d . . . . .
C12 C 0.8778(2) 0.58429(14) 0.21242(13) 0.0136(3) Uani 1 1 d . . . . .
C13 C 0.6093(2) 0.76237(14) 0.15382(13) 0.0139(3) Uani 1 1 d . . . . .
C14 C 0.6306(2) 0.85243(14) 0.12966(13) 0.0154(4) Uani 1 1 d . . . . .
C15 C 0.7198(3) 0.86090(15) 0.06056(14) 0.0189(4) Uani 1 1 d . . . . .
H15 H 0.772204 0.804403 0.028894 0.023 Uiso 1 1 calc R U . . .
C16 C 0.7303(3) 0.95008(17) 0.03966(15) 0.0243(4) Uani 1 1 d . . . . .
H16 H 0.789849 0.955168 -0.006611 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6533(3) 1.03469(16) 0.08639(16) 0.0257(5) Uani 1 1 d . . . . .
H17 H 0.657838 1.095243 0.069225 0.031 Uiso 1 1 calc R U . . .
C18 C 0.5724(3) 1.03108(16) 0.15593(16) 0.0240(4) Uani 1 1 d . . . . .
H18 H 0.524327 1.088957 0.188637 0.029 Uiso 1 1 calc R U . . .
C19 C 0.5622(2) 0.94051(15) 0.17749(14) 0.0180(4) Uani 1 1 d . . . . .
C20 C 0.5270(2) 0.76524(15) 0.22773(13) 0.0153(4) Uani 1 1 d . . . . .
C21 C 0.4948(2) 0.67979(16) 0.25736(14) 0.0193(4) Uani 1 1 d . . . . .
H21 H 0.529168 0.616043 0.226641 0.023 Uiso 1 1 calc R U . . .
C22 C 0.4147(3) 0.68848(18) 0.32979(16) 0.0241(4) Uani 1 1 d . . . . .
H22 H 0.393908 0.630759 0.348853 0.029 Uiso 1 1 calc R U . . .
C23 C 0.3629(3) 0.7824(2) 0.37614(16) 0.0281(5) Uani 1 1 d . . . . .
H23 H 0.309421 0.787447 0.426984 0.034 Uiso 1 1 calc R U . . .
C24 C 0.3885(3) 0.86630(19) 0.34913(16) 0.0264(5) Uani 1 1 d . . . . .
H24 H 0.352909 0.929396 0.380552 0.032 Uiso 1 1 calc R U . . .
C25 C 0.4680(2) 0.85756(16) 0.27432(14) 0.0188(4) Uani 1 1 d . . . . .
C26 C 0.8719(2) 0.69765(14) 0.36840(12) 0.0138(3) Uani 1 1 d . . . . .
C27 C 0.7965(2) 0.68648(15) 0.44086(13) 0.0153(4) Uani 1 1 d . . . . .
C28 C 0.7633(2) 0.59227(15) 0.45631(13) 0.0171(4) Uani 1 1 d . . . . .
H28 H 0.799253 0.532426 0.419118 0.020 Uiso 1 1 calc R U . . .
C29 C 0.6797(3) 0.58791(17) 0.52474(14) 0.0208(4) Uani 1 1 d . . . . .
H29 H 0.658362 0.524777 0.534612 0.025 Uiso 1 1 calc R U . . .
C30 C 0.6249(3) 0.67534(18) 0.58056(15) 0.0231(4) Uani 1 1 d . . . . .
H30 H 0.566574 0.670396 0.627335 0.028 Uiso 1 1 calc R U . . .
C31 C 0.6546(3) 0.76800(17) 0.56840(14) 0.0226(4) Uani 1 1 d . . . . .
H31 H 0.617827 0.827061 0.606292 0.027 Uiso 1 1 calc R U . . .
C32 C 0.7401(2) 0.77298(15) 0.49909(13) 0.0179(4) Uani 1 1 d . . . . .
C33 C 0.8905(2) 0.79483(14) 0.35681(13) 0.0144(3) Uani 1 1 d . . . . .
C34 C 0.9695(2) 0.81497(15) 0.28806(13) 0.0161(4) Uani 1 1 d . . . . .
H34 H 1.013703 0.761596 0.247095 0.019 Uiso 1 1 calc R U . . .
C35 C 0.9822(3) 0.91080(16) 0.28051(14) 0.0201(4) Uani 1 1 d . . . . .
H35 H 1.034480 0.923577 0.234191 0.024 Uiso 1 1 calc R U . . .
C36 C 0.9178(3) 0.99021(16) 0.34133(15) 0.0240(4) Uani 1 1 d . . . . .
H36 H 0.925401 1.056093 0.334668 0.029 Uiso 1 1 calc R U . . .
C37 C 0.8440(3) 0.97457(16) 0.41040(15) 0.0230(4) Uani 1 1 d . . . . .
H37 H 0.802348 1.028876 0.451666 0.028 Uiso 1 1 calc R U . . .
C42 C 0.8321(2) 0.87724(15) 0.41818(13) 0.0173(4) Uani 1 1 d . . . . .
N1 N 0.5282(3) 0.45900(16) 0.27824(16) 0.0365(5) Uani 1 1 d . . . . .
C40 C 0.5998(3) 0.39465(17) 0.24329(15) 0.0251(5) Uani 1 1 d . . . . .
C41 C 0.6909(3) 0.3117(2) 0.1987(2) 0.0356(6) Uani 1 1 d . . . . .
H41A H 0.705641 0.317935 0.139070 0.053 Uiso 1 1 calc R U . . .
H41B H 0.633186 0.248191 0.192083 0.053 Uiso 1 1 calc R U . . .
H41C H 0.795437 0.313068 0.234937 0.053 Uiso 1 1 calc R U . . .
N2 N 0.3139(3) 0.22649(19) 0.1865(2) 0.0485(7) Uani 1 1 d . . . . .
C38 C 0.1940(3) 0.18747(18) 0.18030(17) 0.0302(5) Uani 1 1 d . . . . .
C39 C 0.0362(4) 0.1367(2) 0.1672(2) 0.0481(8) Uani 1 1 d . . . . .
H39A H -0.032464 0.153453 0.117869 0.072 Uiso 1 1 calc R U . . .
H39B H -0.012119 0.158867 0.222763 0.072 Uiso 1 1 calc R U . . .
H39C H 0.048191 0.063955 0.152328 0.072 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 B1 F2 105.7(2) . . ?
F1 B1 F10 102.3(8) . . ?
F1 B1 F11 99.4(4) . . ?
F2 B1 F10 95.0(8) . . ?
F2 B1 F11 145.5(6) . . ?
F3 B1 F1 112.4(3) . . ?
F3 B1 F2 109.3(3) . . ?
F3 B1 F4 110.8(3) . . ?
F3 B1 F10 21.9(7) . . ?
F3 B1 F11 81.6(6) . . ?
F4 B1 F1 109.8(2) . . ?
F4 B1 F2 108.5(2) . . ?
F4 B1 F10 132.3(7) . . ?
F4 B1 F11 39.3(6) . . ?
F9 B1 F1 128.6(6) . . ?
F9 B1 F2 36.4(8) . . ?
F9 B1 F3 113.4(4) . . ?
F9 B1 F4 73.6(8) . . ?
F9 B1 F10 111.8(10) . . ?
F9 B1 F11 109.1(8) . . ?
F10 B1 F11 102.4(8) . . ?
B1 F1 C13 115.13(14) . . ?
F9 F2 B1 66.0(6) . . ?
F10 F3 B1 87(3) . . ?
B1 F4 F9 51.6(5) . . ?
F11 F4 B1 74.4(5) . . ?
F11 F4 F9 120.7(7) . . ?
B1 F9 F4 54.8(5) . . ?
F2 F9 B1 77.5(8) . . ?
F2 F9 F4 129.6(8) . . ?
F3 F10 B1 71(2) . . ?
F4 F11 B1 66.4(7) . . ?
B4 F5 C26 123.17(13) . . ?
F5 B4 F8 105.1(6) . . ?
F5 B4 F12 104.2(17) . . ?
F6 B4 F5 109.03(18) . . ?
F6 B4 F8 106.7(6) . . ?
F6 B4 F12 107.7(10) . . ?
F7 B4 F5 113.4(8) . . ?
F7 B4 F6 111.6(8) . . ?
F7 B4 F8 110.6(8) . . ?
F7 B4 F12 13(2) . . ?
F7 B4 F13 96(2) . . ?
F8 B4 F12 123.6(19) . . ?
F13 B4 F5 111.4(14) . . ?
F13 B4 F6 114.6(16) . . ?
F13 B4 F8 14(3) . . ?
F13 B4 F12 109.3(12) . . ?
C25 O2 C19 120.57(16) . . ?
C42 O3 C32 120.87(16) . . ?
C2 C1 C13 118.83(17) . . ?
C9 C1 C2 115.09(17) . . ?
C9 C1 C13 126.08(17) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 C1 122.43(18) . . ?
C3 C2 H2 118.8 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.01(18) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 122.3 . . ?
C10 C4 C3 115.43(18) . . ?
C10 C4 H4 122.3 . . ?
C6 C5 H5 122.3 . . ?
C11 C5 H5 122.3 . . ?
C11 C5 C6 115.49(18) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.18(18) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.81(19) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C26 120.68(17) . . ?
C12 C8 C7 115.75(17) . . ?
C12 C8 C26 123.58(17) . . ?
C1 C9 C10 121.82(17) . . ?
C1 C9 C12 148.81(18) . . ?
C10 C9 C12 89.22(15) . . ?
C4 C10 C9 123.16(18) . . ?
C4 C10 C11 146.30(18) . . ?
C9 C10 C11 90.53(15) . . ?
C5 C11 C10 146.41(18) . . ?
C5 C11 C12 123.02(18) . . ?
C12 C11 C10 90.57(15) . . ?
C8 C12 C9 148.54(18) . . ?
C8 C12 C11 121.68(17) . . ?
C11 C12 C9 89.68(15) . . ?
F1 C13 C26 158.36(7) . . ?
C1 C13 F1 98.73(12) . . ?
C1 C13 C26 85.07(11) . . ?
C14 C13 F1 72.99(11) . . ?
C14 C13 C1 119.93(17) . . ?
C14 C13 C26 123.50(12) . . ?
C20 C13 F1 95.94(12) . . ?
C20 C13 C1 121.51(17) . . ?
C20 C13 C14 118.53(17) . . ?
C20 C13 C26 64.53(11) . . ?
C13 C14 C15 123.98(18) . . ?
C19 C14 C13 118.82(18) . . ?
C19 C14 C15 117.19(18) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.3(2) . . ?
C19 C18 H18 120.8 . . ?
O2 C19 C14 121.47(18) . . ?
O2 C19 C18 116.05(19) . . ?
C18 C19 C14 122.5(2) . . ?
C13 C20 C21 123.96(18) . . ?
C13 C20 C25 118.96(18) . . ?
C25 C20 C21 117.05(18) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.5(2) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.0(2) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 H24 120.6 . . ?
C23 C24 C25 118.8(2) . . ?
C25 C24 H24 120.6 . . ?
O2 C25 C20 121.55(18) . . ?
O2 C25 C24 116.45(19) . . ?
C24 C25 C20 122.0(2) . . ?
F5 C26 C13 139.96(7) . . ?
C8 C26 F5 112.23(12) . . ?
C8 C26 C13 87.58(11) . . ?
C27 C26 F5 80.39(11) . . ?
C27 C26 C8 121.07(17) . . ?
C27 C26 C13 119.86(12) . . ?
C27 C26 C33 119.05(17) . . ?
C33 C26 F5 78.55(11) . . ?
C33 C26 C8 119.87(17) . . ?
C33 C26 C13 61.48(10) . . ?
C26 C27 C28 124.05(18) . . ?
C26 C27 C32 118.72(18) . . ?
C32 C27 C28 117.09(18) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.08(19) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 121.1(2) . . ?
C30 C29 H29 119.5 . . ?
C29 C30 H30 119.5 . . ?
C31 C30 C29 120.9(2) . . ?
C31 C30 H30 119.5 . . ?
C30 C31 H31 120.8 . . ?
C30 C31 C32 118.3(2) . . ?
C32 C31 H31 120.8 . . ?
O3 C32 C27 121.23(18) . . ?
O3 C32 C31 116.16(18) . . ?
C31 C32 C27 122.5(2) . . ?
C26 C33 C34 123.64(18) . . ?
C42 C33 C26 118.74(17) . . ?
C42 C33 C34 117.59(18) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 C33 120.49(19) . . ?
C35 C34 H34 119.8 . . ?
C34 C35 H35 120.0 . . ?
C34 C35 C36 120.01(19) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 119.3 . . ?
C37 C36 C35 121.5(2) . . ?
C37 C36 H36 119.3 . . ?
C36 C37 H37 120.8 . . ?
C36 C37 C42 118.4(2) . . ?
C42 C37 H37 120.8 . . ?
O3 C42 C33 121.38(18) . . ?
O3 C42 C37 116.60(18) . . ?
C37 C42 C33 122.02(19) . . ?
N1 C40 C41 179.6(3) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N2 C38 C39 177.0(3) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.385(3) . ?
B1 F2 1.407(3) . ?
B1 F3 1.364(5) . ?
B1 F4 1.373(3) . ?
B1 F9 1.317(8) . ?
B1 F10 1.440(17) . ?
B1 F11 1.443(10) . ?
F1 C13 3.170(2) . ?
F2 F9 0.856(18) . ?
F3 F10 0.537(15) . ?
F4 F9 1.612(16) . ?
F4 F11 0.948(16) . ?
F5 B4 1.398(3) . ?
F5 C26 2.979(2) . ?
F6 B4 1.388(3) . ?
F7 B4 1.342(19) . ?
F8 B4 1.404(12) . ?
F12 B4 1.43(3) . ?
F13 B4 1.372(19) . ?
O2 C19 1.354(3) . ?
O2 C25 1.345(3) . ?
O3 C32 1.353(2) . ?
O3 C42 1.352(2) . ?
C1 C2 1.432(3) . ?
C1 C9 1.377(3) . ?
C1 C13 1.476(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.418(3) . ?
C4 H4 0.9500 . ?
C4 C10 1.367(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.421(3) . ?
C5 C11 1.367(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.427(3) . ?
C8 C12 1.378(3) . ?
C8 C26 1.476(3) . ?
C9 C10 1.426(3) . ?
C9 C12 1.525(3) . ?
C10 C11 1.498(3) . ?
C11 C12 1.419(3) . ?
C13 C14 1.416(3) . ?
C13 C20 1.415(3) . ?
C13 C26 4.068(3) . ?
C14 C15 1.424(3) . ?
C14 C19 1.415(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.367(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.412(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.369(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(3) . ?
C20 C21 1.422(3) . ?
C20 C25 1.417(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.370(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.408(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.367(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.399(3) . ?
C26 C27 1.411(3) . ?
C26 C33 1.418(3) . ?
C27 C28 1.425(3) . ?
C27 C32 1.419(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.370(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.406(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.376(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.394(3) . ?
C33 C34 1.423(3) . ?
C33 C42 1.413(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.371(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.406(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.379(3) . ?
C37 H37 0.9500 . ?
C37 C42 1.392(3) . ?
N1 C40 1.134(3) . ?
C40 C41 1.452(4) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
N2 C38 1.128(4) . ?
C38 C39 1.471(4) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 F2 F9 F4 18.3(7) . . . . ?
B1 F4 F9 F2 -22.1(9) . . . . ?
F1 B1 F2 F9 -135.2(7) . . . . ?
F1 B1 F3 F10 -66(3) . . . . ?
F1 B1 F4 F9 125.8(5) . . . . ?
F1 B1 F4 F11 -80.3(6) . . . . ?
F1 B1 F9 F2 60.2(10) . . . . ?
F1 B1 F9 F4 -102.6(7) . . . . ?
F1 B1 F10 F3 120(2) . . . . ?
F1 B1 F11 F4 110.0(5) . . . . ?
F1 C13 C14 C15 -96.65(19) . . . . ?
F1 C13 C14 C19 84.55(17) . . . . ?
F1 C13 C20 C21 104.68(19) . . . . ?
F1 C13 C20 C25 -73.43(18) . . . . ?
F2 B1 F1 C13 -24.4(3) . . . . ?
F2 B1 F3 F10 51(3) . . . . ?
F2 B1 F4 F9 10.7(4) . . . . ?
F2 B1 F4 F11 164.6(6) . . . . ?
F2 B1 F9 F4 -162.8(7) . . . . ?
F2 B1 F10 F3 -132(3) . . . . ?
F2 B1 F11 F4 -26.5(11) . . . . ?
F3 B1 F1 C13 94.8(3) . . . . ?
F3 B1 F2 F9 103.5(7) . . . . ?
F3 B1 F4 F9 -109.3(5) . . . . ?
F3 B1 F4 F11 44.5(7) . . . . ?
F3 B1 F9 F2 -91.2(6) . . . . ?
F3 B1 F9 F4 106.0(4) . . . . ?
F3 B1 F11 F4 -138.5(6) . . . . ?
F4 B1 F1 C13 -141.3(2) . . . . ?
F4 B1 F2 F9 -17.4(7) . . . . ?
F4 B1 F3 F10 171(3) . . . . ?
F4 B1 F9 F2 162.8(7) . . . . ?
F4 B1 F10 F3 -12(3) . . . . ?
F9 B1 F1 C13 -56.8(11) . . . . ?
F9 B1 F3 F10 90(3) . . . . ?
F9 B1 F4 F11 153.9(7) . . . . ?
F9 B1 F10 F3 -99(3) . . . . ?
F9 B1 F11 F4 -26.6(7) . . . . ?
F9 F4 F11 B1 23.7(7) . . . . ?
F10 B1 F1 C13 74.5(9) . . . . ?
F10 B1 F2 F9 120.5(10) . . . . ?
F10 B1 F4 F9 -104.8(12) . . . . ?
F10 B1 F4 F11 49.1(13) . . . . ?
F10 B1 F9 F2 -67.6(9) . . . . ?
F10 B1 F9 F4 129.7(7) . . . . ?
F10 B1 F11 F4 -145.1(9) . . . . ?
F11 B1 F1 C13 179.5(7) . . . . ?
F11 B1 F2 F9 -0.1(11) . . . . ?
F11 B1 F3 F10 -162(3) . . . . ?
F11 B1 F4 F9 -153.9(7) . . . . ?
F11 B1 F9 F2 179.9(7) . . . . ?
F11 B1 F9 F4 17.2(5) . . . . ?
F11 B1 F10 F3 18(3) . . . . ?
F11 F4 F9 B1 -29.6(8) . . . . ?
F11 F4 F9 F2 -51.6(13) . . . . ?
F5 C26 C27 C28 -112.53(19) . . . . ?
F5 C26 C27 C32 71.83(17) . . . . ?
F5 C26 C33 C34 105.62(19) . . . . ?
F5 C26 C33 C42 -72.35(17) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C9 C10 C4 -2.7(3) . . . . ?
C1 C9 C10 C11 176.42(18) . . . . ?
C1 C9 C12 C8 10.2(6) . . . . ?
C1 C9 C12 C11 -174.3(3) . . . . ?
C1 C13 C14 C15 -6.2(3) . . . . ?
C1 C13 C14 C19 174.95(17) . . . . ?
C1 C13 C20 C21 0.6(3) . . . . ?
C1 C13 C20 C25 -177.48(18) . . . . ?
C2 C1 C9 C10 2.2(3) . . . . ?
C2 C1 C9 C12 175.8(3) . . . . ?
C2 C1 C13 F1 20.41(19) . . . . ?
C2 C1 C13 C14 -54.9(3) . . . . ?
C2 C1 C13 C20 122.9(2) . . . . ?
C2 C1 C13 C26 178.94(16) . . . . ?
C2 C3 C4 C10 0.8(3) . . . . ?
C3 C4 C10 C9 1.1(3) . . . . ?
C3 C4 C10 C11 -177.3(3) . . . . ?
C4 C10 C11 C5 -1.1(6) . . . . ?
C4 C10 C11 C12 179.0(3) . . . . ?
C5 C6 C7 C8 -1.8(3) . . . . ?
C5 C11 C12 C8 -3.0(3) . . . . ?
C5 C11 C12 C9 179.75(19) . . . . ?
C6 C5 C11 C10 -178.5(3) . . . . ?
C6 C5 C11 C12 1.4(3) . . . . ?
C6 C7 C8 C12 0.2(3) . . . . ?
C6 C7 C8 C26 -179.81(19) . . . . ?
C7 C8 C12 C9 176.8(3) . . . . ?
C7 C8 C12 C11 2.0(3) . . . . ?
C7 C8 C26 F5 34.1(2) . . . . ?
C7 C8 C26 C13 178.29(17) . . . . ?
C7 C8 C26 C27 -57.9(3) . . . . ?
C7 C8 C26 C33 123.4(2) . . . . ?
C8 C26 C27 C28 -2.3(3) . . . . ?
C8 C26 C27 C32 -177.93(18) . . . . ?
C8 C26 C33 C34 -3.6(3) . . . . ?
C8 C26 C33 C42 178.46(18) . . . . ?
C9 C1 C2 C3 -0.3(3) . . . . ?
C9 C1 C13 F1 -160.02(17) . . . . ?
C9 C1 C13 C14 124.6(2) . . . . ?
C9 C1 C13 C20 -57.5(3) . . . . ?
C9 C1 C13 C26 -1.48(19) . . . . ?
C9 C10 C11 C5 -179.8(3) . . . . ?
C9 C10 C11 C12 0.34(15) . . . . ?
C10 C9 C12 C8 -175.2(3) . . . . ?
C10 C9 C12 C11 0.34(15) . . . . ?
C10 C11 C12 C8 176.94(18) . . . . ?
C10 C11 C12 C9 -0.32(14) . . . . ?
C11 C5 C6 C7 1.0(3) . . . . ?
C12 C8 C26 F5 -145.92(16) . . . . ?
C12 C8 C26 C13 -1.77(19) . . . . ?
C12 C8 C26 C27 122.0(2) . . . . ?
C12 C8 C26 C33 -56.6(3) . . . . ?
C12 C9 C10 C4 -179.42(19) . . . . ?
C12 C9 C10 C11 -0.32(14) . . . . ?
C13 C1 C2 C3 179.31(19) . . . . ?
C13 C1 C9 C10 -177.44(18) . . . . ?
C13 C1 C9 C12 -3.7(5) . . . . ?
C13 C14 C15 C16 178.0(2) . . . . ?
C13 C14 C19 O2 3.3(3) . . . . ?
C13 C14 C19 C18 -177.59(19) . . . . ?
C13 C20 C21 C22 179.8(2) . . . . ?
C13 C20 C25 O2 2.1(3) . . . . ?
C13 C20 C25 C24 -178.6(2) . . . . ?
C13 C26 C27 C28 104.51(19) . . . . ?
C13 C26 C27 C32 -71.1(2) . . . . ?
C13 C26 C33 C34 -72.01(17) . . . . ?
C13 C26 C33 C42 110.02(19) . . . . ?
C14 C13 C20 C21 178.52(19) . . . . ?
C14 C13 C20 C25 0.4(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C14 C19 O2 -175.57(18) . . . . ?
C15 C14 C19 C18 3.5(3) . . . . ?
C15 C16 C17 C18 2.8(4) . . . . ?
C16 C17 C18 C19 -2.5(3) . . . . ?
C17 C18 C19 O2 178.4(2) . . . . ?
C17 C18 C19 C14 -0.7(3) . . . . ?
C19 O2 C25 C20 -1.8(3) . . . . ?
C19 O2 C25 C24 178.80(19) . . . . ?
C19 C14 C15 C16 -3.2(3) . . . . ?
C20 C13 C14 C15 175.83(18) . . . . ?
C20 C13 C14 C19 -3.0(3) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C21 C20 C25 O2 -176.18(18) . . . . ?
C21 C20 C25 C24 3.1(3) . . . . ?
C21 C22 C23 C24 1.3(4) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
C23 C24 C25 O2 177.3(2) . . . . ?
C23 C24 C25 C20 -2.0(3) . . . . ?
C25 O2 C19 C14 -0.9(3) . . . . ?
C25 O2 C19 C18 179.96(19) . . . . ?
C25 C20 C21 C22 -2.1(3) . . . . ?
C26 F5 B4 F6 174.41(12) . . . . ?
C26 F5 B4 F7 49.4(9) . . . . ?
C26 F5 B4 F8 -71.5(6) . . . . ?
C26 F5 B4 F12 59.7(16) . . . . ?
C26 F5 B4 F13 -58(3) . . . . ?
C26 C8 C12 C9 -3.1(4) . . . . ?
C26 C8 C12 C11 -177.90(18) . . . . ?
C26 C13 C14 C15 99.0(2) . . . . ?
C26 C13 C14 C19 -79.8(2) . . . . ?
C26 C13 C20 C21 -65.57(18) . . . . ?
C26 C13 C20 C25 116.32(19) . . . . ?
C26 C27 C28 C29 -175.43(19) . . . . ?
C26 C27 C32 O3 -1.4(3) . . . . ?
C26 C27 C32 C31 175.46(19) . . . . ?
C26 C33 C34 C35 179.61(19) . . . . ?
C26 C33 C42 O3 0.3(3) . . . . ?
C26 C33 C42 C37 -179.1(2) . . . . ?
C27 C26 C33 C34 177.73(18) . . . . ?
C27 C26 C33 C42 -0.2(3) . . . . ?
C27 C28 C29 C30 0.1(3) . . . . ?
C28 C27 C32 O3 -177.35(18) . . . . ?
C28 C27 C32 C31 -0.5(3) . . . . ?
C28 C29 C30 C31 -0.4(3) . . . . ?
C29 C30 C31 C32 0.2(3) . . . . ?
C30 C31 C32 O3 177.27(19) . . . . ?
C30 C31 C32 C27 0.2(3) . . . . ?
C32 O3 C42 C33 -1.0(3) . . . . ?
C32 O3 C42 C37 178.48(19) . . . . ?
C32 C27 C28 C29 0.3(3) . . . . ?
C33 C26 C27 C28 176.39(18) . . . . ?
C33 C26 C27 C32 0.8(3) . . . . ?
C33 C34 C35 C36 0.4(3) . . . . ?
C34 C33 C42 O3 -177.75(18) . . . . ?
C34 C33 C42 C37 2.8(3) . . . . ?
C34 C35 C36 C37 1.3(3) . . . . ?
C35 C36 C37 C42 -0.9(4) . . . . ?
C36 C37 C42 O3 179.4(2) . . . . ?
C36 C37 C42 C33 -1.2(3) . . . . ?
C42 O3 C32 C27 1.5(3) . . . . ?
C42 O3 C32 C31 -175.52(19) . . . . ?
C42 C33 C34 C35 -2.4(3) . . . . ?
