#------------------------------------------------------------------------------
#$Date: 2026-02-24 23:57:06 +0100 (Tue 24 de Feb de 2026) $
#$Revision: 304603 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/54/7135458.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_7135458
loop_
_publ_author_name
'Campillo-Alvarado, Gonzalo'
'Vargas-Olvera, Eva C'
'Swenson, Dale C.'
'Morales-Rojas, Hugo'
'Höpfl, Herbert'
'MacGillivray, Leonard R.'
_publ_section_title
;
 Rotisserie-like motion enables guest transport in a nonporous organic
 crystal involving a diboron host.
;
_journal_issue                   15
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4519
_journal_page_last               4522
_journal_paper_doi               10.1039/d5cc05394c
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C34 H22 B2 F4 N4 O4, 0.5(C6 H6)'
_chemical_formula_sum            'C37 H25 B2 F4 N4 O4'
_chemical_formula_weight         687.23
_chemical_name_systematic
'2,4-difluorophenylboronic acid catechol ester adduct of 4,4,'-azopyridine'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-04-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-04-23 deposited with the CCDC.	2026-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.945(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6124(13)
_cell_length_b                   15.3927(15)
_cell_length_c                   17.4936(17)
_cell_measurement_reflns_used    4422
_cell_measurement_temperature    190.15
_cell_measurement_theta_max      22.22
_cell_measurement_theta_min      2.4215
_cell_volume                     3265.5(6)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      190.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Nonius APEX II Kappa'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_min         2.675
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0570 before and 0.0498 after correction.
The Ratio of minimum to maximum transmission is 0.9504.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       prism
_exptl_crystal_F_000             1412
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6620
_refine_ls_number_restraints     511
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0719
_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)+(0.0941P)²+4.3237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.2171
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3916
_reflns_number_total             6620
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc05394c2.cif
_cod_data_source_block           I
_cod_database_code               7135458
_shelx_shelxl_version_number     2018/3
_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   0.992
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C35-C36 \\sim C36-C37 \\sim C37-C38 \\sim C38-C39 \\sim C39-C40 \\sim C40-C35
 with sigma of 0.02
 C35-C39 \\sim C35-C39 \\sim C38-C36 \\sim C38-C40 \\sim C40-C36 \\sim C39-C37
 with sigma of 0.04
3. Restrained planarity
 C35, C36, C37, C38, C39, C40
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C35, C36, C37, C38, C39, C40
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C37, C38, C39, C40, C36, C35
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Fixed Sof: C38(0.5) H38(0.5) C39(0.5) H39(0.5) C40(0.5) H40(0.5) C35(0.5)
 H35(0.5) C36(0.5) H36(0.5) C37(0.5) H37(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C31(H31), C22(H22), C34(H34), C12(H12), C16(H16),
 C17(H17), C33(H33), C21(H21), C18(H18), C28(H28), C19(H19), C9(H9), C6(H6),
 C3(H3), C4(H4), C25(H25), C5(H5), C11(H11), C26(H26), C27(H27), C38(H38),
 C39(H39), C40(H40), C35(H35), C36(H36), C37(H37)
7.b Fitted hexagon refined as free rotating group:
 C38(C39,C40,C35,C36,C37)
;
_olex2_submission_original_sample_id I-190
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
F3 F -0.20327(17) 0.62305(14) 0.75592(13) 0.0462(5) Uani 1 1 d . . . . .
F4 F -0.44972(19) 0.71023(15) 0.51640(14) 0.0532(6) Uani 1 1 d . . . . .
F1 F 0.69267(19) 0.28338(15) 0.69255(14) 0.0518(5) Uani 1 1 d . . . . .
O2 O 0.4691(2) 0.07020(15) 0.69254(14) 0.0365(4) Uani 1 1 d . . . . .
O3 O -0.05693(19) 0.77601(16) 0.84162(14) 0.0361(4) Uani 1 1 d . . . . .
O1 O 0.6210(2) 0.13831(15) 0.78089(15) 0.0365(4) Uani 1 1 d . . . . .
O4 O 0.01625(19) 0.83748(16) 0.74366(15) 0.0369(4) Uani 1 1 d . . . . .
F2 F 0.7300(2) 0.20629(19) 0.44290(16) 0.0702(7) Uani 1 1 d . . . . .
N1 N 0.4627(2) 0.23075(18) 0.70761(17) 0.0327(4) Uani 1 1 d . . . . .
N4 N 0.0332(2) 0.67761(18) 0.76395(17) 0.0327(4) Uani 1 1 d . . . . .
N2 N 0.2425(2) 0.43556(19) 0.70555(17) 0.0333(5) Uani 1 1 d . . . . .
N3 N 0.2457(2) 0.46705(19) 0.77149(18) 0.0354(5) Uani 1 1 d . . . . .
C2 C 0.4868(3) 0.0365(2) 0.7675(2) 0.0348(6) Uani 1 1 d . . . . .
C7 C 0.5952(3) 0.1608(2) 0.6306(2) 0.0357(4) Uani 1 1 d . . . . .
C13 C 0.4815(3) 0.2834(2) 0.7708(2) 0.0316(6) Uani 1 1 d . . . . .
H13 H 0.544920 0.273835 0.814079 0.038 Uiso 1 1 calc R U . . .
C23 C 0.0094(3) 0.8453(2) 0.8720(2) 0.0328(5) Uani 1 1 d . . . . .
C29 C -0.1589(3) 0.7474(2) 0.6929(2) 0.0321(4) Uani 1 1 d . . . . .
C32 C -0.3542(3) 0.7225(2) 0.5739(2) 0.0372(6) Uani 1 1 d . . . . .
C14 C 0.4118(3) 0.3511(2) 0.7750(2) 0.0326(6) Uani 1 1 d . . . . .
H14 H 0.426078 0.387151 0.820776 0.039 Uiso 1 1 calc R U . . .
C1 C 0.5768(3) 0.0766(2) 0.8194(2) 0.0349(6) Uani 1 1 d . . . . .
C30 C -0.2301(3) 0.6798(2) 0.6932(2) 0.0330(6) Uani 1 1 d . . . . .
C15 C 0.3206(3) 0.3653(2) 0.7112(2) 0.0307(5) Uani 1 1 d . . . . .
C31 C -0.3277(3) 0.6642(2) 0.6353(2) 0.0365(6) Uani 1 1 d . . . . .
H31 H -0.373540 0.615963 0.637939 0.044 Uiso 1 1 calc R U . . .
C20 C 0.1694(3) 0.5386(2) 0.7649(2) 0.0325(6) Uani 1 1 d . . . . .
C22 C 0.0637(3) 0.6258(2) 0.8272(2) 0.0358(6) Uani 1 1 d . . . . .
H22 H 0.036655 0.637334 0.871786 0.043 Uiso 1 1 calc R U . . .
C34 C -0.1923(3) 0.8038(2) 0.6287(2) 0.0358(6) Uani 1 1 d . . . . .
H34 H -0.146134 0.851619 0.625253 0.043 Uiso 1 1 calc R U . . .
C12 C 0.5739(3) 0.1058(3) 0.5641(2) 0.0409(7) Uani 1 1 d . . . . .
H12 H 0.526392 0.057446 0.561973 0.049 Uiso 1 1 calc R U . . .
C24 C 0.0534(3) 0.8814(2) 0.8140(2) 0.0352(6) Uani 1 1 d . . . . .
C8 C 0.6664(3) 0.2287(2) 0.6293(2) 0.0373(6) Uani 1 1 d . . . . .
C16 C 0.3014(3) 0.3120(2) 0.6457(2) 0.0378(7) Uani 1 1 d . . . . .
H16 H 0.239821 0.321425 0.600970 0.045 Uiso 1 1 calc R U . . .
C17 C 0.3734(3) 0.2448(2) 0.6466(2) 0.0382(7) Uani 1 1 d . . . . .
H17 H 0.359356 0.206779 0.602118 0.046 Uiso 1 1 calc R U . . .
C33 C -0.2898(3) 0.7931(2) 0.5697(2) 0.0416(7) Uani 1 1 d . . . . .
H33 H -0.311699 0.833609 0.527252 0.050 Uiso 1 1 calc R U . . .
C21 C 0.1328(3) 0.5564(2) 0.8299(2) 0.0389(7) Uani 1 1 d . . . . .
H21 H 0.154994 0.521293 0.876233 0.047 Uiso 1 1 calc R U . . .
C18 C 0.0700(3) 0.6611(3) 0.7004(2) 0.0398(7) Uani 1 1 d . . . . .
H18 H 0.048781 0.698402 0.655473 0.048 Uiso 1 1 calc R U . . .
C28 C 0.0330(3) 0.8803(2) 0.9470(2) 0.0396(7) Uani 1 1 d . . . . .
H28 H 0.002903 0.856336 0.986529 0.048 Uiso 1 1 calc R U . . .
C19 C 0.1380(3) 0.5914(2) 0.6987(2) 0.0381(7) Uani 1 1 d . . . . .
H19 H 0.162575 0.579883 0.653062 0.046 Uiso 1 1 calc R U . . .
C9 C 0.7126(3) 0.2466(3) 0.5683(2) 0.0443(7) Uani 1 1 d . . . . .
H9 H 0.759627 0.295207 0.569750 0.053 Uiso 1 1 calc R U . . .
C10 C 0.6868(3) 0.1903(3) 0.5054(2) 0.0465(7) Uani 1 1 d . . . . .
C6 C 0.6148(3) 0.0527(2) 0.8983(2) 0.0402(7) Uani 1 1 d . . . . .
H6 H 0.676431 0.080431 0.933497 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4295(3) -0.0283(2) 0.7929(2) 0.0396(6) Uani 1 1 d . . . . .
H3 H 0.367000 -0.055173 0.757846 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4679(3) -0.0529(3) 0.8730(2) 0.0436(7) Uani 1 1 d . . . . .
H4 H 0.430339 -0.097536 0.892657 0.052 Uiso 1 1 calc R U . . .
C25 C 0.1228(3) 0.9520(2) 0.8302(2) 0.0408(7) Uani 1 1 d . . . . .
H25 H 0.153544 0.976059 0.791049 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5579(3) -0.0143(2) 0.9237(2) 0.0444(7) Uani 1 1 d . . . . .
H5 H 0.582297 -0.033582 0.977295 0.053 Uiso 1 1 calc R U . . .
C11 C 0.6199(3) 0.1196(3) 0.5009(3) 0.0506(8) Uani 1 1 d . . . . .
H11 H 0.605199 0.081308 0.456624 0.061 Uiso 1 1 calc R U . . .
C26 C 0.1462(3) 0.9867(3) 0.9070(2) 0.0473(8) Uani 1 1 d . . . . .
H26 H 0.193679 1.035555 0.920223 0.057 Uiso 1 1 calc R U . . .
C27 C 0.1024(3) 0.9521(3) 0.9631(2) 0.0454(8) Uani 1 1 d . . . . .
H27 H 0.119682 0.977611 1.014482 0.054 Uiso 1 1 calc R U . . .
B1 B 0.5425(3) 0.1455(3) 0.7024(3) 0.0358(3) Uani 1 1 d . . . . .
B2 B -0.0465(3) 0.7633(3) 0.7608(3) 0.0350(3) Uani 1 1 d . . . . .
C38 C -0.0448(12) 0.5603(6) 0.9946(8) 0.119(3) Uani 0.5 1 d DG U P A -1
H38 H -0.088143 0.611696 0.983992 0.143 Uiso 0.5 1 calc R U P A -1
C39 C -0.0815(10) 0.4851(8) 0.9516(7) 0.127(3) Uani 0.5 1 d DG U P A -1
H39 H -0.149892 0.484958 0.911561 0.152 Uiso 0.5 1 calc R U P A -1
C40 C -0.0181(12) 0.4099(6) 0.9671(8) 0.119(3) Uani 0.5 1 d DG U P A -1
H40 H -0.043127 0.358456 0.937664 0.143 Uiso 0.5 1 calc R U P A -1
C35 C 0.0820(12) 0.4100(6) 1.0256(8) 0.118(3) Uani 0.5 1 d DG U P A -1
H35 H 0.125388 0.358690 1.036199 0.142 Uiso 0.5 1 calc R U P A -1
C36 C 0.1187(10) 0.4853(8) 1.0686(7) 0.122(3) Uani 0.5 1 d DG U P A -1
H36 H 0.187139 0.485426 1.108629 0.147 Uiso 0.5 1 calc R U P A -1
C37 C 0.0553(12) 0.5605(6) 1.0531(7) 0.121(3) Uani 0.5 1 d DG U P A -1
H37 H 0.080375 0.611930 1.082528 0.145 Uiso 0.5 1 calc R U P A -1
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
C2 O2 B1 104.8(3) . . ?
C23 O3 B2 105.7(3) . . ?
C1 O1 B1 104.7(3) . . ?
C24 O4 B2 105.7(3) . . ?
C13 N1 C17 118.7(3) . . ?
C13 N1 B1 123.2(3) . . ?
C17 N1 B1 118.0(3) . . ?
C22 N4 C18 119.3(3) . . ?
C22 N4 B2 122.7(3) . . ?
C18 N4 B2 118.0(3) . . ?
N3 N2 C15 112.4(3) . . ?
N2 N3 C20 111.8(3) . . ?
O2 C2 C1 110.2(3) . . ?
O2 C2 C3 128.4(4) . . ?
C3 C2 C1 121.3(3) . . ?
C12 C7 B1 122.5(3) . . ?
C8 C7 C12 114.8(3) . . ?
C8 C7 B1 122.7(3) . . ?
N1 C13 H13 119.0 . . ?
N1 C13 C14 122.1(3) . . ?
C14 C13 H13 119.0 . . ?
O3 C23 C24 110.5(3) . . ?
O3 C23 C28 128.7(3) . . ?
C28 C23 C24 120.8(3) . . ?
C30 C29 C34 115.1(3) . . ?
C30 C29 B2 124.0(3) . . ?
C34 C29 B2 120.9(3) . . ?
F4 C32 C31 117.8(3) . . ?
F4 C32 C33 119.4(3) . . ?
C31 C32 C33 122.8(4) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.5(3) . . ?
C15 C14 H14 120.7 . . ?
O1 C1 C2 111.0(3) . . ?
O1 C1 C6 126.9(3) . . ?
C6 C1 C2 122.1(3) . . ?
F3 C30 C29 117.9(3) . . ?
F3 C30 C31 116.7(3) . . ?
C29 C30 C31 125.3(3) . . ?
C14 C15 N2 125.0(3) . . ?
C16 C15 N2 115.3(3) . . ?
C16 C15 C14 119.7(3) . . ?
C32 C31 C30 115.9(3) . . ?
C32 C31 H31 122.0 . . ?
C30 C31 H31 122.0 . . ?
C21 C20 N3 117.1(3) . . ?
C21 C20 C19 119.6(3) . . ?
C19 C20 N3 123.2(3) . . ?
N4 C22 H22 119.0 . . ?
N4 C22 C21 122.0(3) . . ?
C21 C22 H22 119.0 . . ?
C29 C34 H34 118.7 . . ?
C33 C34 C29 122.6(3) . . ?
C33 C34 H34 118.7 . . ?
C7 C12 H12 118.7 . . ?
C11 C12 C7 122.5(4) . . ?
C11 C12 H12 118.7 . . ?
O4 C24 C23 110.5(3) . . ?
O4 C24 C25 128.0(3) . . ?
C25 C24 C23 121.5(3) . . ?
F1 C8 C7 118.0(3) . . ?
F1 C8 C9 116.6(3) . . ?
C9 C8 C7 125.5(4) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 C15 118.4(3) . . ?
C17 C16 H16 120.8 . . ?
N1 C17 C16 122.6(4) . . ?
N1 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
C32 C33 C34 118.3(4) . . ?
C32 C33 H33 120.9 . . ?
C34 C33 H33 120.9 . . ?
C20 C21 C22 118.9(4) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
N4 C18 H18 119.2 . . ?
N4 C18 C19 121.5(4) . . ?
C19 C18 H18 119.2 . . ?
C23 C28 H28 121.2 . . ?
C23 C28 C27 117.7(4) . . ?
C27 C28 H28 121.2 . . ?
C20 C19 C18 118.6(3) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C8 C9 H9 122.0 . . ?
C10 C9 C8 116.0(4) . . ?
C10 C9 H9 122.0 . . ?
C9 C10 F2 117.9(4) . . ?
C11 C10 F2 118.1(4) . . ?
C11 C10 C9 124.0(4) . . ?
C1 C6 H6 121.7 . . ?
C1 C6 C5 116.6(4) . . ?
C5 C6 H6 121.7 . . ?
C2 C3 H3 121.6 . . ?
C2 C3 C4 116.8(4) . . ?
C4 C3 H3 121.6 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(4) . . ?
C5 C4 H4 119.1 . . ?
C24 C25 H25 121.5 . . ?
C24 C25 C26 117.0(4) . . ?
C26 C25 H25 121.5 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C12 C11 H11 121.4 . . ?
C10 C11 C12 117.3(4) . . ?
C10 C11 H11 121.4 . . ?
C25 C26 H26 119.2 . . ?
C27 C26 C25 121.5(4) . . ?
C27 C26 H26 119.2 . . ?
C28 C27 H27 119.2 . . ?
C26 C27 C28 121.6(4) . . ?
C26 C27 H27 119.2 . . ?
O2 B1 N1 104.9(3) . . ?
O2 B1 C7 114.4(3) . . ?
O1 B1 O2 107.1(3) . . ?
O1 B1 N1 105.7(3) . . ?
O1 B1 C7 115.6(3) . . ?
C7 B1 N1 108.3(3) . . ?
O3 B2 N4 106.8(3) . . ?
O3 B2 C29 116.1(3) . . ?
O4 B2 O3 106.8(3) . . ?
O4 B2 N4 105.8(3) . . ?
O4 B2 C29 112.7(3) . . ?
C29 B2 N4 108.1(3) . . ?
C39 C38 H38 120.0 . . ?
C39 C38 C37 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C39 H39 120.0 . . ?
C38 C39 C40 120.0 . . ?
C40 C39 H39 120.0 . . ?
C39 C40 H40 120.0 . . ?
C35 C40 C39 120.0 . . ?
C35 C40 H40 120.0 . . ?
C40 C35 H35 120.0 . . ?
C40 C35 C36 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 120.0 . . ?
C35 C36 C37 120.0 . . ?
C37 C36 H36 120.0 . . ?
C38 C37 H37 120.0 . . ?
C36 C37 C38 120.0 . . ?
C36 C37 H37 120.0 . . ?
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
F3 C30 1.370(4) . ?
F4 C32 1.353(4) . ?
F1 C8 1.357(4) . ?
O2 C2 1.370(4) . ?
O2 B1 1.463(5) . ?
O3 C23 1.369(4) . ?
O3 B2 1.469(5) . ?
O1 C1 1.367(4) . ?
O1 B1 1.460(5) . ?
O4 C24 1.369(4) . ?
O4 B2 1.466(5) . ?
F2 C10 1.372(4) . ?
N1 C13 1.338(4) . ?
N1 C17 1.339(5) . ?
N1 B1 1.672(5) . ?
N4 C22 1.331(5) . ?
N4 C18 1.341(4) . ?
N4 B2 1.650(5) . ?
N2 N3 1.242(4) . ?
N2 C15 1.447(4) . ?
N3 C20 1.446(4) . ?
C2 C1 1.388(5) . ?
C2 C3 1.375(5) . ?
C7 C12 1.403(5) . ?
C7 C8 1.382(5) . ?
C7 B1 1.591(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.378(5) . ?
C23 C24 1.398(5) . ?
C23 C28 1.374(5) . ?
C29 C30 1.374(5) . ?
C29 C34 1.390(5) . ?
C29 B2 1.599(6) . ?
C32 C31 1.369(5) . ?
C32 C33 1.371(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(5) . ?
C1 C6 1.381(5) . ?
C30 C31 1.384(5) . ?
C15 C16 1.375(5) . ?
C31 H31 0.9500 . ?
C20 C21 1.368(5) . ?
C20 C19 1.379(5) . ?
C22 H22 0.9500 . ?
C22 C21 1.372(5) . ?
C34 H34 0.9500 . ?
C34 C33 1.382(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.399(5) . ?
C24 C25 1.375(5) . ?
C8 C9 1.377(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(5) . ?
C17 H17 0.9500 . ?
C33 H33 0.9500 . ?
C21 H21 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.379(5) . ?
C28 H28 0.9500 . ?
C28 C27 1.389(5) . ?
C19 H19 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.367(6) . ?
C10 C11 1.366(6) . ?
C6 H6 0.9500 . ?
C6 C5 1.397(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.370(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.400(5) . ?
C5 H5 0.9500 . ?
C11 H11 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.359(6) . ?
C27 H27 0.9500 . ?
C38 H38 0.9500 . ?
C38 C39 1.3900 . ?
C38 C37 1.3900 . ?
C39 H39 0.9500 . ?
C39 C40 1.3900 . ?
C40 H40 0.9500 . ?
C40 C35 1.3900 . ?
C35 H35 0.9500 . ?
C35 C36 1.3900 . ?
C36 H36 0.9500 . ?
C36 C37 1.3900 . ?
C37 H37 0.9500 . ?
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
F3 C30 C31 C32 178.8(3) . . . . ?
F4 C32 C31 C30 -179.3(3) . . . . ?
F4 C32 C33 C34 -179.4(3) . . . . ?
F1 C8 C9 C10 179.1(3) . . . . ?
O2 C2 C1 O1 0.5(4) . . . . ?
O2 C2 C1 C6 -177.8(3) . . . . ?
O2 C2 C3 C4 177.6(3) . . . . ?
O3 C23 C24 O4 0.7(4) . . . . ?
O3 C23 C24 C25 180.0(3) . . . . ?
O3 C23 C28 C27 -179.2(3) . . . . ?
O1 C1 C6 C5 -178.0(3) . . . . ?
O4 C24 C25 C26 178.3(3) . . . . ?
F2 C10 C11 C12 -178.1(4) . . . . ?
N1 C13 C14 C15 -1.0(5) . . . . ?
N4 C22 C21 C20 -1.7(6) . . . . ?
N4 C18 C19 C20 -0.9(6) . . . . ?
N2 N3 C20 C21 155.1(3) . . . . ?
N2 N3 C20 C19 -28.7(5) . . . . ?
N2 C15 C16 C17 179.0(3) . . . . ?
N3 N2 C15 C14 -19.7(4) . . . . ?
N3 N2 C15 C16 162.5(3) . . . . ?
N3 C20 C21 C22 177.5(3) . . . . ?
N3 C20 C19 C18 -176.0(3) . . . . ?
C2 O2 B1 O1 14.6(3) . . . . ?
C2 O2 B1 N1 -97.4(3) . . . . ?
C2 O2 B1 C7 144.0(3) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C7 C12 C11 C10 -0.7(6) . . . . ?
C7 C8 C9 C10 -1.7(6) . . . . ?
C13 N1 C17 C16 1.1(5) . . . . ?
C13 N1 B1 O2 119.6(3) . . . . ?
C13 N1 B1 O1 6.5(4) . . . . ?
C13 N1 B1 C7 -117.9(4) . . . . ?
C13 C14 C15 N2 -177.5(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C23 O3 B2 O4 -8.3(4) . . . . ?
C23 O3 B2 N4 104.5(3) . . . . ?
C23 O3 B2 C29 -135.0(3) . . . . ?
C23 C24 C25 C26 -0.9(5) . . . . ?
C23 C28 C27 C26 -0.2(6) . . . . ?
C29 C30 C31 C32 -0.9(5) . . . . ?
C29 C34 C33 C32 -1.9(5) . . . . ?
C14 C15 C16 C17 1.0(5) . . . . ?
C1 O1 B1 O2 -14.2(3) . . . . ?
C1 O1 B1 N1 97.2(3) . . . . ?
C1 O1 B1 C7 -143.0(3) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C1 C6 C5 C4 -1.3(5) . . . . ?
C30 C29 C34 C33 0.2(5) . . . . ?
C30 C29 B2 O3 -59.2(5) . . . . ?
C30 C29 B2 O4 177.1(3) . . . . ?
C30 C29 B2 N4 60.6(4) . . . . ?
C15 N2 N3 C20 178.5(3) . . . . ?
C15 C16 C17 N1 -1.8(6) . . . . ?
C31 C32 C33 C34 2.2(6) . . . . ?
C22 N4 C18 C19 0.5(5) . . . . ?
C22 N4 B2 O3 9.4(4) . . . . ?
C22 N4 B2 O4 122.9(3) . . . . ?
C22 N4 B2 C29 -116.1(3) . . . . ?
C34 C29 C30 F3 -178.4(3) . . . . ?
C34 C29 C30 C31 1.2(5) . . . . ?
C34 C29 B2 O3 119.7(4) . . . . ?
C34 C29 B2 O4 -4.0(5) . . . . ?
C34 C29 B2 N4 -120.5(3) . . . . ?
C12 C7 C8 F1 -178.6(3) . . . . ?
C12 C7 C8 C9 2.2(5) . . . . ?
C12 C7 B1 O2 -0.8(5) . . . . ?
C12 C7 B1 O1 124.3(4) . . . . ?
C12 C7 B1 N1 -117.4(4) . . . . ?
C24 O4 B2 O3 8.7(4) . . . . ?
C24 O4 B2 N4 -104.8(3) . . . . ?
C24 O4 B2 C29 137.4(3) . . . . ?
C24 C23 C28 C27 -0.5(5) . . . . ?
C24 C25 C26 C27 0.2(6) . . . . ?
C8 C7 C12 C11 -0.9(5) . . . . ?
C8 C7 B1 O2 179.9(3) . . . . ?
C8 C7 B1 O1 -55.0(5) . . . . ?
C8 C7 B1 N1 63.3(4) . . . . ?
C8 C9 C10 F2 179.3(3) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C17 N1 C13 C14 0.3(5) . . . . ?
C17 N1 B1 O2 -57.9(4) . . . . ?
C17 N1 B1 O1 -171.0(3) . . . . ?
C17 N1 B1 C7 64.6(4) . . . . ?
C33 C32 C31 C30 -0.9(5) . . . . ?
C21 C20 C19 C18 0.0(5) . . . . ?
C18 N4 C22 C21 0.8(5) . . . . ?
C18 N4 B2 O3 -169.3(3) . . . . ?
C18 N4 B2 O4 -55.7(4) . . . . ?
C18 N4 B2 C29 65.2(4) . . . . ?
C28 C23 C24 O4 -178.3(3) . . . . ?
C28 C23 C24 C25 1.1(5) . . . . ?
C19 C20 C21 C22 1.2(5) . . . . ?
C9 C10 C11 C12 1.4(6) . . . . ?
C3 C2 C1 O1 179.5(3) . . . . ?
C3 C2 C1 C6 1.2(5) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C25 C26 C27 C28 0.4(6) . . . . ?
B1 O2 C2 C1 -9.5(4) . . . . ?
B1 O2 C2 C3 171.7(3) . . . . ?
B1 O1 C1 C2 8.7(4) . . . . ?
B1 O1 C1 C6 -173.1(3) . . . . ?
B1 N1 C13 C14 -177.2(3) . . . . ?
B1 N1 C17 C16 178.7(3) . . . . ?
B1 C7 C12 C11 179.7(4) . . . . ?
B1 C7 C8 F1 0.8(5) . . . . ?
B1 C7 C8 C9 -178.4(3) . . . . ?
B2 O3 C23 C24 4.9(4) . . . . ?
B2 O3 C23 C28 -176.3(4) . . . . ?
B2 O4 C24 C23 -5.9(4) . . . . ?
B2 O4 C24 C25 174.8(4) . . . . ?
B2 N4 C22 C21 -177.9(3) . . . . ?
B2 N4 C18 C19 179.3(3) . . . . ?
B2 C29 C30 F3 0.5(5) . . . . ?
B2 C29 C30 C31 -179.8(3) . . . . ?
B2 C29 C34 C33 -178.8(3) . . . . ?
C38 C39 C40 C35 0.0 . . . . ?
C39 C38 C37 C36 0.0 . . . . ?
C39 C40 C35 C36 0.0 . . . . ?
C40 C35 C36 C37 0.0 . . . . ?
C35 C36 C37 C38 0.0 . . . . ?
C37 C38 C39 C40 0.0 . . . . ?
