#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/63/7106395.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_7106395
loop_
_publ_author_name
'Zachariah Heiden'
'Douglas Stephan'
_publ_section_title
;
 Metal-Free Diastereoselective Catalytic Hydrogenations of Imines Using
 B(C6F5)3+
;
_journal_name_full               Chem.Commun.
_journal_page_first              5729
_journal_paper_doi               10.1039/c1cc10438a
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C35 H27 B F15 N'
_chemical_formula_sum            'C35 H27 B F15 N'
_chemical_formula_weight         757.39
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.315(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.0599(8)
_cell_length_b                   10.8893(5)
_cell_length_c                   18.3548(8)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.12
_cell_measurement_theta_min      2.29
_cell_volume                     3263.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            62851
_diffrn_reflns_theta_full        36.41
_diffrn_reflns_theta_max         36.41
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     951
_refine_ls_number_reflns         29412
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.108
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0791P)²+0.5712P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1846
_reflns_number_gt                16105
_reflns_number_total             29412
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10438a.txt
_cod_data_source_block           zmh031_4
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7106395
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.57238(9) 0.78073(16) 0.74816(9) 0.0416(4) Uani 1 1 d . . .
F2 F 0.69326(11) 0.69555(17) 0.71652(11) 0.0515(4) Uani 1 1 d . . .
F3 F 0.80469(10) 0.85341(19) 0.70380(11) 0.0543(5) Uani 1 1 d . . .
F4 F 0.79025(10) 1.09964(19) 0.72496(12) 0.0567(5) Uani 1 1 d . . .
F5 F 0.67302(9) 1.18462(16) 0.76019(10) 0.0423(4) Uani 1 1 d . . .
F6 F 0.66184(10) 1.13038(17) 0.93229(9) 0.0521(4) Uani 1 1 d . . .
F7 F 0.69476(15) 1.0512(2) 1.07968(10) 0.0835(7) Uani 1 1 d . . .
F8 F 0.61566(16) 0.8499(2) 1.10085(11) 0.0855(8) Uani 1 1 d . . .
F9 F 0.50363(12) 0.7304(2) 0.97003(12) 0.0659(6) Uani 1 1 d . . .
F10 F 0.46574(9) 0.81281(16) 0.82187(9) 0.0450(4) Uani 1 1 d . . .
F11 F 0.40672(8) 1.12694(15) 0.80158(8) 0.0357(3) Uani 1 1 d . . .
F12 F 0.24779(8) 1.09862(15) 0.70476(9) 0.0407(4) Uani 1 1 d . . .
F13 F 0.19983(8) 0.96623(16) 0.56566(9) 0.0439(4) Uani 1 1 d . . .
F14 F 0.31519(9) 0.87592(17) 0.52179(8) 0.0450(4) Uani 1 1 d . . .
F15 F 0.47348(8) 0.91461(16) 0.61286(8) 0.0395(4) Uani 1 1 d . . .
F16 F 1.03457(10) 0.23854(17) 0.17188(10) 0.0493(4) Uani 1 1 d . . .
F17 F 0.99767(14) 0.3187(2) 0.02396(12) 0.0719(6) Uani 1 1 d . . .
F18 F 0.88371(16) 0.1991(3) -0.10676(11) 0.0872(8) Uani 1 1 d . . .
F19 F 0.80652(15) -0.0033(2) -0.08450(10) 0.0814(7) Uani 1 1 d . . .
F20 F 0.83947(11) -0.08060(18) 0.06340(10) 0.0552(5) Uani 1 1 d . . .
F21 F 0.83297(9) -0.13132(15) 0.24486(9) 0.0405(3) Uani 1 1 d . . .
F22 F 0.71633(10) -0.04437(17) 0.28162(11) 0.0501(4) Uani 1 1 d . . .
F23 F 0.69969(11) 0.20309(18) 0.29693(11) 0.0544(5) Uani 1 1 d . . .
F24 F 0.80523(11) 0.36066(15) 0.27471(10) 0.0490(4) Uani 1 1 d . . .
F25 F 0.92410(9) 0.27489(15) 0.23773(9) 0.0390(3) Uani 1 1 d . . .
F26 F 1.02686(8) 0.15662(16) 0.37717(8) 0.0418(4) Uani 1 1 d . . .
F27 F 1.18470(9) 0.19052(17) 0.46933(9) 0.0467(4) Uani 1 1 d . . .
F28 F 1.30062(8) 0.08727(18) 0.43066(10) 0.0498(4) Uani 1 1 d . . .
F29 F 1.25316(10) -0.05763(19) 0.29733(11) 0.0537(5) Uani 1 1 d . . .
F30 F 1.09405(9) -0.08535(16) 0.19929(9) 0.0444(4) Uani 1 1 d . . .
N1 N 0.09841(11) 0.1073(2) 0.74408(11) 0.0330(4) Uani 1 1 d . . .
H1A H 0.1374 0.1385 0.7294 0.040 Uiso 1 1 calc R . .
H1B H 0.0938 0.0245 0.7331 0.040 Uiso 1 1 calc R . .
N2 N 0.42421(19) 0.8818(3) 0.24765(15) 0.0695(9) Uani 1 1 d . . .
H2A H 0.3805 0.8582 0.2576 0.083 Uiso 1 1 calc R . .
H2B H 0.4576 0.8144 0.2565 0.083 Uiso 1 1 calc R . .
C1 C 0.01711(12) 0.1689(2) 0.69470(12) 0.0338(5) Uani 1 1 d . . .
H1 H 0.0189 0.2540 0.7157 0.041 Uiso 1 1 calc R . .
C2 C -0.00700(13) 0.1763(2) 0.60397(13) 0.0332(4) Uani 1 1 d . . .
C3 C -0.0727(2) 0.2783(3) 0.5758(2) 0.0674(10) Uani 1 1 d . . .
H3A H -0.0538 0.3513 0.6111 0.081 Uiso 1 1 calc R . .
H3B H -0.0864 0.3031 0.5196 0.081 Uiso 1 1 calc R . .
C4 C -0.1457(2) 0.2193(4) 0.5821(2) 0.0743(12) Uani 1 1 d . . .
H4A H -0.1935 0.2162 0.5289 0.089 Uiso 1 1 calc R . .
H4B H -0.1612 0.2650 0.6203 0.089 Uiso 1 1 calc R . .
C5 C -0.11579(16) 0.0902(4) 0.61337(16) 0.0554(8) Uani 1 1 d . . .
H5 H -0.1606 0.0292 0.6029 0.066 Uiso 1 1 calc R . .
C6 C -0.05332(15) 0.0988(4) 0.70195(15) 0.0557(9) Uani 1 1 d . . .
H6A H -0.0356 0.0164 0.7259 0.067 Uiso 1 1 calc R . .
H6B H -0.0757 0.1450 0.7345 0.067 Uiso 1 1 calc R . .
C7 C 0.06235(18) 0.1989(4) 0.58044(16) 0.0577(9) Uani 1 1 d . . .
H7A H 0.0935 0.2712 0.6091 0.087 Uiso 1 1 calc R . .
H7B H 0.0400 0.2131 0.5222 0.087 Uiso 1 1 calc R . .
H7C H 0.0985 0.1271 0.5947 0.087 Uiso 1 1 calc R . .
C8 C -0.06024(14) 0.0614(2) 0.56962(13) 0.0351(5) Uani 1 1 d . . .
C9 C -0.1069(2) 0.0621(4) 0.47699(15) 0.0590(8) Uani 1 1 d . . .
H9A H -0.1353 0.1408 0.4592 0.089 Uiso 1 1 calc R . .
H9B H -0.1470 -0.0048 0.4597 0.089 Uiso 1 1 calc R . .
H9C H -0.0681 0.0509 0.4532 0.089 Uiso 1 1 calc R . .
C10 C -0.0139(3) -0.0599(3) 0.5935(2) 0.0811(13) Uani 1 1 d . . .
H10A H 0.0337 -0.0570 0.5809 0.122 Uiso 1 1 calc R . .
H10B H -0.0501 -0.1272 0.5634 0.122 Uiso 1 1 calc R . .
H10C H 0.0046 -0.0735 0.6514 0.122 Uiso 1 1 calc R . .
C11 C 0.12650(15) 0.1267(3) 0.83532(14) 0.0400(5) Uani 1 1 d . . .
H11A H 0.1432 0.2131 0.8500 0.048 Uiso 1 1 calc R . .
H11B H 0.0813 0.1075 0.8503 0.048 Uiso 1 1 calc R . .
C12 C 0.19746(15) 0.0425(2) 0.87832(12) 0.0339(5) Uani 1 1 d . . .
C13 C 0.18554(18) -0.0700(3) 0.90633(14) 0.0422(6) Uani 1 1 d . . .
H13 H 0.1329 -0.0910 0.9024 0.051 Uiso 1 1 calc R . .
C14 C 0.2495(2) -0.1522(3) 0.93994(17) 0.0545(8) Uani 1 1 d . . .
H14 H 0.2403 -0.2301 0.9579 0.065 Uiso 1 1 calc R . .
C15 C 0.3267(2) -0.1214(4) 0.94749(18) 0.0609(9) Uani 1 1 d . . .
H15 H 0.3707 -0.1779 0.9708 0.073 Uiso 1 1 calc R . .
C16 C 0.33955(18) -0.0083(4) 0.92093(17) 0.0547(8) Uani 1 1 d . . .
H16 H 0.3926 0.0130 0.9260 0.066 Uiso 1 1 calc R . .
C17 C 0.27510(16) 0.0747(3) 0.88668(14) 0.0423(6) Uani 1 1 d . . .
H17 H 0.2842 0.1530 0.8691 0.051 Uiso 1 1 calc R . .
C18 C 0.61485(12) 0.9868(2) 0.75470(12) 0.0288(5) Uani 1 1 d . . .
C19 C 0.62533(14) 0.8630(2) 0.74381(13) 0.0313(5) Uani 1 1 d . . .
C20 C 0.68769(16) 0.8161(3) 0.72718(14) 0.0371(6) Uani 1 1 d . . .
C21 C 0.74427(14) 0.8961(3) 0.72080(14) 0.0374(6) Uani 1 1 d . . .
C22 C 0.73629(14) 1.0197(3) 0.73069(14) 0.0396(6) Uani 1 1 d . . .
C23 C 0.67317(13) 1.0611(3) 0.74842(13) 0.0326(5) Uani 1 1 d . . .
C24 C 0.56102(13) 0.9778(2) 0.86928(12) 0.0284(5) Uani 1 1 d . . .
C25 C 0.61966(15) 1.0314(3) 0.93862(14) 0.0380(6) Uani 1 1 d . . .
C26 C 0.6384(2) 0.9924(3) 1.01528(15) 0.0525(8) Uani 1 1 d . . .
C27 C 0.5990(2) 0.8906(4) 1.02651(15) 0.0551(9) Uani 1 1 d . . .
C28 C 0.54105(18) 0.8312(3) 0.95966(17) 0.0450(7) Uani 1 1 d . . .
C29 C 0.52329(14) 0.8764(3) 0.88343(14) 0.0335(5) Uani 1 1 d . . .
C30 C 0.44863(12) 1.0142(2) 0.71546(12) 0.0254(4) Uani 1 1 d . . .
C31 C 0.38690(12) 1.0609(2) 0.73308(12) 0.0266(4) Uani 1 1 d . . .
C32 C 0.30410(13) 1.0474(2) 0.68433(14) 0.0302(5) Uani 1 1 d . . .
C33 C 0.28001(12) 0.9817(2) 0.61358(13) 0.0311(5) Uani 1 1 d . . .
C34 C 0.33810(13) 0.9375(3) 0.59121(13) 0.0317(5) Uani 1 1 d . . .
C35 C 0.42056(13) 0.9567(2) 0.64169(12) 0.0284(4) Uani 1 1 d . . .
C36 C 0.46959(17) 0.9750(3) 0.30635(15) 0.0512(7) Uani 1 1 d . . .
H36 H 0.4311 1.0455 0.2969 0.061 Uiso 1 1 calc R . .
C37 C 0.49804(15) 0.9372(3) 0.39566(14) 0.0420(6) Uani 1 1 d . . .
C38 C 0.4995(2) 1.0588(3) 0.43679(19) 0.0605(8) Uani 1 1 d . . .
H38A H 0.5070 1.0465 0.4930 0.073 Uiso 1 1 calc R . .
H38B H 0.4486 1.1063 0.4069 0.073 Uiso 1 1 calc R . .
C39 C 0.5755(3) 1.1234(3) 0.4338(2) 0.0723(10) Uani 1 1 d . . .
H39A H 0.5593 1.2008 0.4025 0.087 Uiso 1 1 calc R . .
H39B H 0.6175 1.1420 0.4888 0.087 Uiso 1 1 calc R . .
C40 C 0.60741(16) 1.0301(3) 0.39214(17) 0.0498(7) Uani 1 1 d . . .
H40 H 0.6658 1.0428 0.4022 0.060 Uiso 1 1 calc R . .
C41 C 0.54715(16) 1.0286(3) 0.30272(17) 0.0508(7) Uani 1 1 d . . .
H41A H 0.5669 0.9754 0.2710 0.061 Uiso 1 1 calc R . .
H41B H 0.5372 1.1124 0.2795 0.061 Uiso 1 1 calc R . .
C42 C 0.4477(2) 0.8380(5) 0.4131(2) 0.0802(14) Uani 1 1 d . . .
H42A H 0.4634 0.8345 0.4712 0.120 Uiso 1 1 calc R . .
H42B H 0.4582 0.7582 0.3946 0.120 Uiso 1 1 calc R . .
H42C H 0.3893 0.8577 0.3846 0.120 Uiso 1 1 calc R . .
C43 C 0.59104(15) 0.9070(3) 0.42457(15) 0.0415(5) Uani 1 1 d . . .
C44 C 0.63746(18) 0.8929(3) 0.51612(17) 0.0553(7) Uani 1 1 d . . .
H44A H 0.6170 0.8205 0.5336 0.083 Uiso 1 1 calc R . .
H44B H 0.6290 0.9662 0.5426 0.083 Uiso 1 1 calc R . .
H44C H 0.6961 0.8829 0.5308 0.083 Uiso 1 1 calc R . .
C45 C 0.6101(3) 0.7963(4) 0.3856(2) 0.0806(13) Uani 1 1 d . . .
H45A H 0.5821 0.8044 0.3269 0.121 Uiso 1 1 calc R . .
H45B H 0.5913 0.7217 0.4023 0.121 Uiso 1 1 calc R . .
H45C H 0.6694 0.7913 0.4025 0.121 Uiso 1 1 calc R . .
C46 C 0.3921(2) 0.9151(4) 0.16068(17) 0.0729(11) Uani 1 1 d . . .
H46A H 0.3754 0.8386 0.1285 0.088 Uiso 1 1 calc R . .
H46B H 0.4374 0.9517 0.1512 0.088 Uiso 1 1 calc R . .
C47 C 0.3210(2) 1.0026(3) 0.12950(16) 0.0537(8) Uani 1 1 d . . .
C48 C 0.3320(2) 1.1195(3) 0.10548(18) 0.0550(8) Uani 1 1 d . . .
H48 H 0.3841 1.1427 0.1090 0.066 Uiso 1 1 calc R . .
C49 C 0.2685(3) 1.2020(3) 0.0767(2) 0.0675(10) Uani 1 1 d . . .
H49 H 0.2768 1.2822 0.0612 0.081 Uiso 1 1 calc R . .
C50 C 0.1931(3) 1.1676(4) 0.0706(2) 0.0751(11) Uani 1 1 d . . .
H50 H 0.1491 1.2246 0.0507 0.090 Uiso 1 1 calc R . .
C51 C 0.1800(3) 1.0504(4) 0.0931(3) 0.0759(11) Uani 1 1 d . . .
H51 H 0.1273 1.0276 0.0883 0.091 Uiso 1 1 calc R . .
C52 C 0.2434(3) 0.9683(4) 0.12208(19) 0.0647(10) Uani 1 1 d . . .
H52 H 0.2348 0.8880 0.1372 0.078 Uiso 1 1 calc R . .
C53 C 0.93959(13) 0.0740(2) 0.12594(12) 0.0292(5) Uani 1 1 d . . .
C54 C 0.97717(15) 0.1758(3) 0.11089(14) 0.0369(5) Uani 1 1 d . . .
C55 C 0.95874(19) 0.2181(3) 0.03332(18) 0.0490(7) Uani 1 1 d . . .
C56 C 0.9012(2) 0.1585(4) -0.03223(16) 0.0567(9) Uani 1 1 d . . .
C57 C 0.8627(2) 0.0589(3) -0.02114(14) 0.0527(8) Uani 1 1 d . . .
C58 C 0.88115(16) 0.0184(3) 0.05709(14) 0.0381(6) Uani 1 1 d . . .
C59 C 0.88615(13) 0.0680(2) 0.23998(12) 0.0261(4) Uani 1 1 d . . .
C60 C 0.82981(13) -0.0073(2) 0.25171(13) 0.0280(4) Uani 1 1 d . . .
C61 C 0.76741(14) 0.0357(3) 0.27016(13) 0.0329(5) Uani 1 1 d . . .
C62 C 0.75871(15) 0.1598(3) 0.27772(14) 0.0368(6) Uani 1 1 d . . .
C63 C 0.81231(16) 0.2386(2) 0.26628(14) 0.0339(5) Uani 1 1 d . . .
C64 C 0.87285(15) 0.1916(2) 0.24759(13) 0.0311(5) Uani 1 1 d . . .
C65 C 1.05109(13) 0.0385(2) 0.28004(12) 0.0259(4) Uani 1 1 d . . .
C66 C 1.07997(14) 0.1054(2) 0.35185(13) 0.0293(5) Uani 1 1 d . . .
C67 C 1.16207(15) 0.1219(3) 0.40186(14) 0.0330(5) Uani 1 1 d . . .
C68 C 1.22086(13) 0.0682(3) 0.38311(15) 0.0357(5) Uani 1 1 d . . .
C69 C 1.19599(15) -0.0014(3) 0.31478(15) 0.0354(5) Uani 1 1 d . . .
C70 C 1.11331(14) -0.0148(2) 0.26493(13) 0.0310(5) Uani 1 1 d . . .
B1 B 0.54357(14) 1.0365(3) 0.78077(14) 0.0262(5) Uani 1 1 d . . .
B2 B 0.95645(15) 0.0165(3) 0.21433(14) 0.0270(5) Uani 1 1 d . . .
H100 H 0.5454(16) 1.136(3) 0.7869(16) 0.033(7) Uiso 1 1 d . . .
H101 H 0.9454(13) -0.091(2) 0.2050(13) 0.015(5) Uiso 1 1 d . . .
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'
N N 0.0061 0.0033 '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'
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
C1 N1 C11 111.95(17) . . ?
C1 N1 H1A 109.2 . . ?
C11 N1 H1A 109.2 . . ?
C1 N1 H1B 109.2 . . ?
C11 N1 H1B 109.2 . . ?
H1A N1 H1B 107.9 . . ?
C36 N2 C46 117.5(3) . . ?
C36 N2 H2A 107.9 . . ?
C46 N2 H2A 107.9 . . ?
C36 N2 H2B 107.9 . . ?
C46 N2 H2B 107.9 . . ?
H2A N2 H2B 107.2 . . ?
N1 C1 C2 115.24(18) . . ?
N1 C1 C6 110.8(2) . . ?
C2 C1 C6 105.02(18) . . ?
N1 C1 H1 108.5 . . ?
C2 C1 H1 108.5 . . ?
C6 C1 H1 108.5 . . ?
C7 C2 C1 115.75(19) . . ?
C7 C2 C8 117.7(2) . . ?
C1 C2 C8 103.85(19) . . ?
C7 C2 C3 113.6(3) . . ?
C1 C2 C3 102.8(2) . . ?
C8 C2 C3 101.0(2) . . ?
C4 C3 C2 103.9(3) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C5 103.8(2) . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C5 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C4 C5 C6 108.9(3) . . ?
C4 C5 C8 101.2(2) . . ?
C6 C5 C8 102.4(2) . . ?
C4 C5 H5 114.3 . . ?
C6 C5 H5 114.3 . . ?
C8 C5 H5 114.3 . . ?
C5 C6 C1 101.5(2) . . ?
C5 C6 H6A 111.5 . . ?
C1 C6 H6A 111.5 . . ?
C5 C6 H6B 111.5 . . ?
C1 C6 H6B 111.5 . . ?
H6A C6 H6B 109.3 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C8 C2 114.6(2) . . ?
C10 C8 C9 107.2(2) . . ?
C2 C8 C9 113.5(2) . . ?
C10 C8 C5 114.9(3) . . ?
C2 C8 C5 92.98(19) . . ?
C9 C8 C5 113.4(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 107.4(2) . . ?
C12 C11 H11A 110.2 . . ?
N1 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
N1 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C13 C12 C17 119.6(3) . . ?
C13 C12 C11 120.4(2) . . ?
C17 C12 C11 120.0(3) . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 119.7(3) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C23 C18 C19 113.8(2) . . ?
C23 C18 B1 123.7(2) . . ?
C19 C18 B1 122.3(2) . . ?
F1 C19 C20 115.8(2) . . ?
F1 C19 C18 119.8(2) . . ?
C20 C19 C18 124.4(2) . . ?
F2 C20 C19 120.9(3) . . ?
F2 C20 C21 120.0(2) . . ?
C19 C20 C21 119.0(3) . . ?
F3 C21 C22 120.9(3) . . ?
F3 C21 C20 120.3(3) . . ?
C22 C21 C20 118.8(2) . . ?
F4 C22 C21 120.2(2) . . ?
F4 C22 C23 120.3(3) . . ?
C21 C22 C23 119.5(3) . . ?
F5 C23 C18 121.0(2) . . ?
F5 C23 C22 114.5(2) . . ?
C18 C23 C22 124.4(3) . . ?
C29 C24 C25 114.1(2) . . ?
C29 C24 B1 126.53(19) . . ?
C25 C24 B1 119.4(2) . . ?
F6 C25 C26 115.8(2) . . ?
F6 C25 C24 119.5(2) . . ?
C26 C25 C24 124.7(3) . . ?
F7 C26 C25 121.2(3) . . ?
F7 C26 C27 119.7(3) . . ?
C25 C26 C27 119.1(3) . . ?
F8 C27 C26 120.8(3) . . ?
F8 C27 C28 120.1(4) . . ?
C26 C27 C28 119.1(2) . . ?
F9 C28 C29 121.3(3) . . ?
F9 C28 C27 119.4(3) . . ?
C29 C28 C27 119.3(3) . . ?
F10 C29 C24 121.2(2) . . ?
F10 C29 C28 115.1(3) . . ?
C24 C29 C28 123.7(2) . . ?
C35 C30 C31 113.73(18) . . ?
C35 C30 B1 128.15(19) . . ?
C31 C30 B1 118.09(18) . . ?
F11 C31 C32 116.1(2) . . ?
F11 C31 C30 119.45(17) . . ?
C32 C31 C30 124.5(2) . . ?
F12 C32 C33 120.35(19) . . ?
F12 C32 C31 120.8(2) . . ?
C33 C32 C31 118.8(2) . . ?
F13 C33 C34 120.6(2) . . ?
F13 C33 C32 119.9(2) . . ?
C34 C33 C32 119.45(19) . . ?
F14 C34 C33 119.83(18) . . ?
F14 C34 C35 121.0(2) . . ?
C33 C34 C35 119.1(2) . . ?
F15 C35 C30 120.89(18) . . ?
F15 C35 C34 114.93(19) . . ?
C30 C35 C34 124.2(2) . . ?
N2 C36 C41 117.8(3) . . ?
N2 C36 C37 115.2(3) . . ?
C41 C36 C37 104.4(2) . . ?
N2 C36 H36 106.2 . . ?
C41 C36 H36 106.2 . . ?
C37 C36 H36 106.2 . . ?
C38 C37 C42 113.4(3) . . ?
C38 C37 C36 102.8(2) . . ?
C42 C37 C36 116.8(2) . . ?
C38 C37 C43 103.1(2) . . ?
C42 C37 C43 115.3(3) . . ?
C36 C37 C43 103.7(2) . . ?
C37 C38 C39 101.7(3) . . ?
C37 C38 H38A 111.4 . . ?
C39 C38 H38A 111.4 . . ?
C37 C38 H38B 111.4 . . ?
C39 C38 H38B 111.4 . . ?
H38A C38 H38B 109.3 . . ?
C40 C39 C38 104.1(3) . . ?
C40 C39 H39A 110.9 . . ?
C38 C39 H39A 110.9 . . ?
C40 C39 H39B 110.9 . . ?
C38 C39 H39B 110.9 . . ?
H39A C39 H39B 109.0 . . ?
C39 C40 C41 107.2(3) . . ?
C39 C40 C43 102.1(2) . . ?
C41 C40 C43 103.8(2) . . ?
C39 C40 H40 114.2 . . ?
C41 C40 H40 114.2 . . ?
C43 C40 H40 114.2 . . ?
C40 C41 C36 101.5(2) . . ?
C40 C41 H41A 111.5 . . ?
C36 C41 H41A 111.5 . . ?
C40 C41 H41B 111.5 . . ?
C36 C41 H41B 111.5 . . ?
H41A C41 H41B 109.3 . . ?
C37 C42 H42A 109.5 . . ?
C37 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C37 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C45 C43 C44 108.0(2) . . ?
C45 C43 C40 112.9(3) . . ?
C44 C43 C40 113.9(2) . . ?
C45 C43 C37 115.8(3) . . ?
C44 C43 C37 113.4(2) . . ?
C40 C43 C37 92.4(2) . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N2 C46 C47 116.1(3) . . ?
N2 C46 H46A 108.3 . . ?
C47 C46 H46A 108.3 . . ?
N2 C46 H46B 108.3 . . ?
C47 C46 H46B 108.3 . . ?
H46A C46 H46B 107.4 . . ?
C48 C47 C52 119.1(4) . . ?
C48 C47 C46 119.2(3) . . ?
C52 C47 C46 121.7(3) . . ?
C49 C48 C47 120.9(4) . . ?
C49 C48 H48 119.6 . . ?
C47 C48 H48 119.6 . . ?
C50 C49 C48 119.4(3) . . ?
C50 C49 H49 120.3 . . ?
C48 C49 H49 120.3 . . ?
C49 C50 C51 121.0(4) . . ?
C49 C50 H50 119.5 . . ?
C51 C50 H50 119.5 . . ?
C52 C51 C50 119.6(4) . . ?
C52 C51 H51 120.2 . . ?
C50 C51 H51 120.2 . . ?
C51 C52 C47 120.0(3) . . ?
C51 C52 H52 120.0 . . ?
C47 C52 H52 120.0 . . ?
C54 C53 C58 114.4(2) . . ?
C54 C53 B2 127.0(2) . . ?
C58 C53 B2 118.7(2) . . ?
F16 C54 C53 120.6(2) . . ?
F16 C54 C55 116.5(3) . . ?
C53 C54 C55 122.9(3) . . ?
F17 C55 C56 120.8(3) . . ?
F17 C55 C54 119.2(3) . . ?
C56 C55 C54 120.0(3) . . ?
F18 C56 C57 120.5(3) . . ?
F18 C56 C55 119.9(3) . . ?
C57 C56 C55 119.6(2) . . ?
C56 C57 F19 121.2(3) . . ?
C56 C57 C58 119.7(3) . . ?
F19 C57 C58 119.1(3) . . ?
F20 C58 C53 120.3(2) . . ?
F20 C58 C57 116.3(2) . . ?
C53 C58 C57 123.4(3) . . ?
C64 C59 C60 112.8(2) . . ?
C64 C59 B2 123.6(2) . . ?
C60 C59 B2 123.5(2) . . ?
F21 C60 C61 115.3(2) . . ?
F21 C60 C59 120.5(2) . . ?
C61 C60 C59 124.2(2) . . ?
F22 C61 C62 120.3(2) . . ?
F22 C61 C60 120.0(2) . . ?
C62 C61 C60 119.7(2) . . ?
F23 C62 C61 120.6(3) . . ?
F23 C62 C63 120.7(3) . . ?
C61 C62 C63 118.7(2) . . ?
F24 C63 C62 119.3(2) . . ?
F24 C63 C64 121.2(2) . . ?
C62 C63 C64 119.4(2) . . ?
F25 C64 C63 116.3(2) . . ?
F25 C64 C59 118.5(2) . . ?
C63 C64 C59 125.2(2) . . ?
C70 C65 C66 113.41(19) . . ?
C70 C65 B2 118.03(19) . . ?
C66 C65 B2 128.6(2) . . ?
F26 C66 C67 115.8(2) . . ?
F26 C66 C65 120.38(19) . . ?
C67 C66 C65 123.8(2) . . ?
F27 C67 C68 120.0(2) . . ?
F27 C67 C66 119.9(2) . . ?
C68 C67 C66 120.1(2) . . ?
F28 C68 C69 121.5(2) . . ?
F28 C68 C67 119.9(2) . . ?
C69 C68 C67 118.6(2) . . ?
F29 C69 C68 119.0(2) . . ?
F29 C69 C70 120.9(2) . . ?
C68 C69 C70 120.2(2) . . ?
F30 C70 C69 116.4(2) . . ?
F30 C70 C65 119.7(2) . . ?
C69 C70 C65 123.9(2) . . ?
C30 B1 C18 116.31(17) . . ?
C30 B1 C24 111.34(17) . . ?
C18 B1 C24 108.42(19) . . ?
C30 B1 H100 101.5(14) . . ?
C18 B1 H100 111.4(14) . . ?
C24 B1 H100 107.5(14) . . ?
C59 B2 C65 115.74(18) . . ?
C59 B2 C53 108.41(18) . . ?
C65 B2 C53 111.54(18) . . ?
C59 B2 H101 106.1(11) . . ?
C65 B2 H101 108.0(10) . . ?
C53 B2 H101 106.5(11) . . ?
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
F1 C19 1.338(3) . ?
F2 C20 1.338(3) . ?
F3 C21 1.340(3) . ?
F4 C22 1.344(3) . ?
F5 C23 1.362(3) . ?
F6 C25 1.353(3) . ?
F7 C26 1.346(4) . ?
F8 C27 1.341(3) . ?
F9 C28 1.345(4) . ?
F10 C29 1.354(3) . ?
F11 C31 1.357(2) . ?
F12 C32 1.346(3) . ?
F13 C33 1.345(2) . ?
F14 C34 1.339(3) . ?
F15 C35 1.355(3) . ?
F16 C54 1.342(3) . ?
F17 C55 1.352(4) . ?
F18 C56 1.341(3) . ?
F19 C57 1.353(4) . ?
F20 C58 1.348(3) . ?
F21 C60 1.360(3) . ?
F22 C61 1.349(3) . ?
F23 C62 1.343(3) . ?
F24 C63 1.350(3) . ?
F25 C64 1.362(3) . ?
F26 C66 1.352(3) . ?
F27 C67 1.351(3) . ?
F28 C68 1.343(3) . ?
F29 C69 1.351(3) . ?
F30 C70 1.343(3) . ?
N1 C1 1.513(3) . ?
N1 C11 1.543(3) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
N2 C36 1.452(4) . ?
N2 C46 1.491(4) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
C1 C2 1.533(3) . ?
C1 C6 1.537(4) . ?
C1 H1 1.0000 . ?
C2 C7 1.509(4) . ?
C2 C8 1.540(3) . ?
C2 C3 1.544(4) . ?
C3 C4 1.515(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.528(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.535(4) . ?
C5 C8 1.562(4) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C10 1.524(4) . ?
C8 C9 1.541(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.497(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.380(4) . ?
C12 C17 1.389(4) . ?
C13 C14 1.380(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.372(3) . ?
C18 C19 1.387(4) . ?
C18 B1 1.645(3) . ?
C19 C20 1.384(3) . ?
C20 C21 1.385(4) . ?
C21 C22 1.374(5) . ?
C22 C23 1.388(3) . ?
C24 C29 1.379(4) . ?
C24 C25 1.389(3) . ?
C24 B1 1.646(3) . ?
C25 C26 1.366(4) . ?
C26 C27 1.379(5) . ?
C27 C28 1.387(5) . ?
C28 C29 1.385(3) . ?
C30 C35 1.377(3) . ?
C30 C31 1.384(3) . ?
C30 B1 1.636(3) . ?
C31 C32 1.384(3) . ?
C32 C33 1.380(3) . ?
C33 C34 1.367(3) . ?
C34 C35 1.393(3) . ?
C36 C41 1.545(4) . ?
C36 C37 1.549(3) . ?
C36 H36 1.0000 . ?
C37 C38 1.519(5) . ?
C37 C42 1.531(5) . ?
C37 C43 1.565(4) . ?
C38 C39 1.565(5) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.526(5) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.533(4) . ?
C40 C43 1.545(4) . ?
C40 H40 1.0000 . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C45 1.514(4) . ?
C43 C44 1.532(4) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 C47 1.503(5) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.389(4) . ?
C47 C52 1.399(5) . ?
C48 C49 1.371(5) . ?
C48 H48 0.9500 . ?
C49 C50 1.370(6) . ?
C49 H49 0.9500 . ?
C50 C51 1.392(6) . ?
C50 H50 0.9500 . ?
C51 C52 1.369(6) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 C54 1.388(4) . ?
C53 C58 1.392(3) . ?
C53 B2 1.641(3) . ?
C54 C55 1.395(4) . ?
C55 C56 1.371(5) . ?
C56 C57 1.350(5) . ?
C57 C58 1.399(4) . ?
C59 C64 1.385(4) . ?
C59 C60 1.394(3) . ?
C59 B2 1.631(3) . ?
C60 C61 1.389(3) . ?
C61 C62 1.375(4) . ?
C62 C63 1.375(4) . ?
C63 C64 1.377(3) . ?
C65 C70 1.394(3) . ?
C65 C66 1.397(3) . ?
C65 B2 1.634(3) . ?
C66 C67 1.382(3) . ?
C67 C68 1.379(4) . ?
C68 C69 1.367(4) . ?
C69 C70 1.386(3) . ?
B1 H100 1.09(3) . ?
B2 H101 1.18(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139181898
