#------------------------------------------------------------------------------
#$Date: 2026-04-05 13:38:01 +0200 (Sun 05 de Apr de 2026) $
#$Revision: 305292 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/55/7135593.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_7135593
loop_
_publ_author_name
'Mboyi, Clève D'
'Sabbadin, Henri'
'Penouilh, Marie-José'
'Bonnin, Quentin'
'Amardeil, Régine'
'Cattey, Hélène'
'Fournier, Sophie'
'Devillers, Charles H.'
'Roger, Julien'
'Hierso, Jean-Cyrille'
_publ_section_title
;
 Small cavitand macrocycles from direct C-C coupling of s-aryl
 tetrazine units.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6987
_journal_page_last               6991
_journal_paper_doi               10.1039/d6cc00124f
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C42 H18 F6 N12, C4 H8 O'
_chemical_formula_sum            'C46 H26 F6 N12 O'
_chemical_formula_weight         876.79
_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     dual
_audit_update_record
;
2025-11-07 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.2020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5165(8)
_cell_length_b                   12.9555(7)
_cell_length_c                   21.3838(11)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    110
_cell_measurement_theta_max      27.040
_cell_measurement_theta_min      2.450
_cell_volume                     3945.0(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      110
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            74654
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.092
_diffrn_reflns_theta_min         2.218
_diffrn_source                   'X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_source_voltage           20.0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.9333.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       prism
_exptl_crystal_F_000             1792
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of diethylether and DCM  by slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         8675
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0688P)²+3.7167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5333
_reflns_number_total             8675
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6cc00124f2.cif
_cod_data_source_block           Compound_6b
_cod_depositor_comments
'Adding full bibliography for 7135589--7135593.cif.'
_cod_database_code               7135593
_shelx_shelxl_version_number     2019/3
_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   0.978
_shelx_estimated_absorpt_t_min   0.967
_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. Restrained distances
 O1-C45 \\sim O1B-C45B
 with sigma of 0.02
 O1-C44 \\sim O1B-C44B
 with sigma of 0.02
 C46-C45 \\sim C46B-C45B
 with sigma of 0.02
 O1-C46 \\sim O1B-C46B
 with sigma of 0.04
 C43-C44 \\sim C43B-C44B
 with sigma of 0.02
 O1-C43 \\sim O1B-C43B
 with sigma of 0.04
 C45-C44 \\sim C45B-C44B
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C44B \\sim C43B \\sim O1B \\sim C45B \\sim C46B \\sim C44 \\sim O1 \\sim C45
\\sim C46 \\sim C43: within 1.7A with sigma of 0.004 and sigma for terminal
atoms of 0.008 within 1.7A
4. Others
 Fixed Sof: O1(0.75) C46(0.75) H46A(0.75) H46B(0.75) H46C(0.75) C45(0.75)
 H45(0.75) C43(0.75) H43A(0.75) H43B(0.75) H43C(0.75) C44(0.75) H44(0.75)
 C43B(0.25) H43D(0.25) H43E(0.25) H43F(0.25) C44B(0.25) H44B(0.25) O1B(0.25)
 C45B(0.25) H45B(0.25) C46B(0.25) H46D(0.25) H46E(0.25) H46F(0.25)
5.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C20(H20), C24(H24), C19(H19), C25(H25), C18(H18), C34(H34),
 C37(H37), C33(H33), C32(H32), C6(H6), C39(H39), C4(H4), C9(H9), C38(H38),
 C5(H5), C11(H11), C10(H10), C45(H45), C44(H44), C44B(H44B), C45B(H45B)
5.b Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C43(H43A,H43B,H43C), C43B(H43D,H43E,H43F), C46B(H46D,
 H46E,H46F)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop with oil'
_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
F4 F 0.87758(11) -0.07145(13) 0.32259(7) 0.0372(4) Uani 1 1 d . . . . .
F1 F 0.53728(11) 0.59220(13) 0.41858(7) 0.0366(4) Uani 1 1 d . . . . .
F3 F 0.52213(11) 0.38981(12) 0.33186(8) 0.0366(4) Uani 1 1 d . . . . .
F6 F 0.46236(11) 0.28667(14) 0.45806(7) 0.0401(4) Uani 1 1 d . . . . .
F5 F 0.98692(11) 0.11744(14) 0.56873(7) 0.0409(4) Uani 1 1 d . . . . .
F2 F 1.01631(12) 0.38371(14) 0.34589(9) 0.0478(5) Uani 1 1 d . . . . .
N5 N 0.70426(15) 0.02718(17) 0.41158(9) 0.0263(5) Uani 1 1 d . . . . .
N7 N 0.84968(15) 0.10041(18) 0.39846(9) 0.0288(5) Uani 1 1 d . . . . .
N4 N 0.67265(16) 0.40112(17) 0.27478(10) 0.0273(5) Uani 1 1 d . . . . .
N6 N 0.72543(15) 0.04932(17) 0.47393(9) 0.0273(5) Uani 1 1 d . . . . .
N8 N 0.86779(15) 0.12800(18) 0.45878(9) 0.0289(5) Uani 1 1 d . . . . .
N2 N 0.76337(15) 0.25938(17) 0.31931(10) 0.0273(5) Uani 1 1 d . . . . .
N3 N 0.74713(16) 0.46233(17) 0.29168(10) 0.0279(5) Uani 1 1 d . . . . .
N1 N 0.83760(16) 0.31973(17) 0.33593(10) 0.0289(5) Uani 1 1 d . . . . .
N12 N 0.71382(17) 0.39655(18) 0.42248(10) 0.0322(5) Uani 1 1 d . . . . .
N11 N 0.69045(17) 0.30984(18) 0.44955(11) 0.0326(5) Uani 1 1 d . . . . .
N9 N 0.65429(18) 0.40791(19) 0.53398(10) 0.0358(6) Uani 1 1 d . . . . .
N10 N 0.67961(18) 0.49355(19) 0.50761(10) 0.0353(6) Uani 1 1 d . . . . .
C27 C 0.74331(18) 0.03338(19) 0.30642(11) 0.0228(5) Uani 1 1 d . . . . .
C22 C 0.66507(18) 0.07320(19) 0.26405(11) 0.0227(5) Uani 1 1 d . . . . .
C28 C 0.76544(18) 0.05594(19) 0.37609(11) 0.0228(5) Uani 1 1 d . . . . .
C2 C 0.69624(19) 0.5818(2) 0.41067(11) 0.0257(6) Uani 1 1 d . . . . .
C41 C 0.60254(18) 0.2307(2) 0.52225(11) 0.0242(6) Uani 1 1 d . . . . .
C42 C 0.65001(17) 0.3208(2) 0.50000(11) 0.0241(6) Uani 1 1 d . . . . .
C7 C 0.77176(19) 0.6232(2) 0.38709(12) 0.0272(6) Uani 1 1 d . . . . .
C23 C 0.65290(19) 0.0470(2) 0.19963(11) 0.0262(6) Uani 1 1 d . . . . .
H23 H 0.600427 0.073814 0.170615 0.031 Uiso 1 1 calc R U . . .
C30 C 0.82363(18) 0.1414(2) 0.56175(11) 0.0250(6) Uani 1 1 d . . . . .
C21 C 0.58882(17) 0.1351(2) 0.28462(11) 0.0227(5) Uani 1 1 d . . . . .
C29 C 0.80372(18) 0.1038(2) 0.49465(11) 0.0242(6) Uani 1 1 d . . . . .
C36 C 0.64978(19) 0.1603(2) 0.56654(11) 0.0260(6) Uani 1 1 d . . . . .
C20 C 0.50409(18) 0.0846(2) 0.28406(11) 0.0266(6) Uani 1 1 d . . . . .
H20 H 0.499019 0.013301 0.273560 0.032 Uiso 1 1 calc R U . . .
C1 C 0.69721(18) 0.4859(2) 0.44825(11) 0.0240(6) Uani 1 1 d . . . . .
C16 C 0.59478(18) 0.2420(2) 0.29830(11) 0.0242(6) Uani 1 1 d . . . . .
C26 C 0.80392(18) -0.0300(2) 0.28140(12) 0.0266(6) Uani 1 1 d . . . . .
C8 C 0.86903(19) 0.5789(2) 0.39914(12) 0.0291(6) Uani 1 1 d . . . . .
C24 C 0.7155(2) -0.0173(2) 0.17688(12) 0.0298(6) Uani 1 1 d . . . . .
H24 H 0.705898 -0.033469 0.132757 0.036 Uiso 1 1 calc R U . . .
C19 C 0.42698(19) 0.1355(2) 0.29840(12) 0.0288(6) Uani 1 1 d . . . . .
H19 H 0.369689 0.099321 0.297004 0.035 Uiso 1 1 calc R U . . .
C35 C 0.75195(18) 0.1725(2) 0.59378(11) 0.0249(6) Uani 1 1 d . . . . .
C15 C 0.67993(18) 0.3047(2) 0.29896(11) 0.0244(6) Uani 1 1 d . . . . .
C17 C 0.51594(19) 0.2888(2) 0.31411(12) 0.0277(6) Uani 1 1 d . . . . .
C40 C 0.50706(19) 0.2166(2) 0.50032(12) 0.0297(6) Uani 1 1 d . . . . .
C25 C 0.7917(2) -0.0577(2) 0.21836(12) 0.0303(6) Uani 1 1 d . . . . .
H25 H 0.834381 -0.103135 0.203783 0.036 Uiso 1 1 calc R U . . .
C3 C 0.61089(19) 0.6338(2) 0.39713(12) 0.0291(6) Uani 1 1 d . . . . .
C14 C 0.82224(19) 0.4219(2) 0.33097(12) 0.0264(6) Uani 1 1 d . . . . .
C18 C 0.43310(19) 0.2386(2) 0.31470(12) 0.0298(6) Uani 1 1 d . . . . .
H18 H 0.381313 0.273820 0.326024 0.036 Uiso 1 1 calc R U . . .
C13 C 0.89373(19) 0.4899(2) 0.36842(12) 0.0288(6) Uani 1 1 d . . . . .
C31 C 0.91560(19) 0.1520(2) 0.59530(12) 0.0300(6) Uani 1 1 d . . . . .
C34 C 0.7753(2) 0.2162(2) 0.65433(12) 0.0299(6) Uani 1 1 d . . . . .
H34 H 0.726700 0.237836 0.675353 0.036 Uiso 1 1 calc R U . . .
C37 C 0.5995(2) 0.0808(2) 0.58856(13) 0.0329(6) Uani 1 1 d . . . . .
H37 H 0.631261 0.033947 0.619576 0.039 Uiso 1 1 calc R U . . .
C33 C 0.8675(2) 0.2285(2) 0.68428(12) 0.0336(7) Uani 1 1 d . . . . .
H33 H 0.882047 0.260325 0.725035 0.040 Uiso 1 1 calc R U . . .
C32 C 0.9389(2) 0.1947(2) 0.65516(12) 0.0333(6) Uani 1 1 d . . . . .
H32 H 1.002685 0.200801 0.676000 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7589(2) 0.7160(2) 0.35343(13) 0.0347(7) Uani 1 1 d . . . . .
H6 H 0.810384 0.745955 0.338587 0.042 Uiso 1 1 calc R U . . .
C39 C 0.4573(2) 0.1366(2) 0.52094(13) 0.0345(7) Uani 1 1 d . . . . .
H39 H 0.392121 0.128143 0.504455 0.041 Uiso 1 1 calc R U . . .
C12 C 0.9889(2) 0.4643(2) 0.37798(14) 0.0354(7) Uani 1 1 d . . . . .
C4 C 0.5969(2) 0.7239(2) 0.36232(13) 0.0366(7) Uani 1 1 d . . . . .
H4 H 0.537115 0.756315 0.353210 0.044 Uiso 1 1 calc R U . . .
C9 C 0.9392(2) 0.6346(2) 0.43918(13) 0.0368(7) Uani 1 1 d . . . . .
H9 H 0.922625 0.694581 0.460069 0.044 Uiso 1 1 calc R U . . .
C38 C 0.5046(2) 0.0695(2) 0.56595(13) 0.0356(7) Uani 1 1 d . . . . .
H38 H 0.471503 0.014988 0.581513 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6729(2) 0.7654(2) 0.34120(13) 0.0391(7) Uani 1 1 d . . . . .
H5 H 0.665992 0.828403 0.318046 0.047 Uiso 1 1 calc R U . . .
C11 C 1.0580(2) 0.5193(3) 0.41743(15) 0.0425(8) Uani 1 1 d . . . . .
H11 H 1.122001 0.499140 0.422707 0.051 Uiso 1 1 calc R U . . .
C10 C 1.0327(2) 0.6043(3) 0.44910(15) 0.0423(8) Uani 1 1 d . . . . .
H10 H 1.078982 0.641873 0.477624 0.051 Uiso 1 1 calc R U . . .
O1 O 0.8132(3) 0.6886(3) 0.15020(16) 0.0669(9) Uani 0.75 1 d D U P A 1
C46 C 0.7788(4) 0.7519(4) 0.0491(3) 0.0586(13) Uani 0.75 1 d D U P A 1
H46A H 0.770577 0.733147 0.003954 0.088 Uiso 0.75 1 calc R U P A 1
H46B H 0.827066 0.805550 0.058959 0.088 Uiso 0.75 1 calc R U P A 1
H46C H 0.719306 0.778098 0.057966 0.088 Uiso 0.75 1 calc R U P A 1
C45 C 0.8076(4) 0.6616(5) 0.0882(3) 0.0723(12) Uani 0.75 1 d D U P A 1
H45 H 0.820328 0.595180 0.073055 0.087 Uiso 0.75 1 calc R U P A 1
C43 C 0.9501(6) 0.6098(6) 0.2107(4) 0.0915(19) Uani 0.75 1 d D U P A 1
H43A H 0.975538 0.577977 0.176051 0.137 Uiso 0.75 1 calc R U P A 1
H43B H 0.969298 0.569252 0.249764 0.137 Uiso 0.75 1 calc R U P A 1
H43C H 0.974264 0.680295 0.217804 0.137 Uiso 0.75 1 calc R U P A 1
C44 C 0.8542(4) 0.6122(5) 0.1946(3) 0.0779(12) Uani 0.75 1 d D U P A 1
H44 H 0.816548 0.564679 0.212373 0.093 Uiso 0.75 1 calc R U P A 1
C43B C 0.9582(19) 0.573(2) 0.2261(9) 0.083(3) Uiso 0.25 1 d D U P B 2
H43D H 0.926855 0.505807 0.220208 0.124 Uiso 0.25 1 calc R U P B 2
H43E H 0.926405 0.617198 0.252494 0.124 Uiso 0.25 1 calc R U P B 2
H43F H 1.023890 0.563589 0.247141 0.124 Uiso 0.25 1 calc R U P B 2
C44B C 0.9547(12) 0.6184(15) 0.1683(8) 0.078(2) Uiso 0.25 1 d D U P B 2
H44B H 1.009851 0.629547 0.151549 0.094 Uiso 0.25 1 calc R U P B 2
O1B O 0.8682(9) 0.6470(10) 0.1356(5) 0.0755(13) Uiso 0.25 1 d D U P B 2
C45B C 0.8771(13) 0.6706(14) 0.0759(7) 0.076(2) Uiso 0.25 1 d D U P B 2
H45B H 0.934657 0.657997 0.062377 0.091 Uiso 0.25 1 calc R U P B 2
C46B C 0.8032(14) 0.7126(16) 0.0351(9) 0.076(3) Uiso 0.25 1 d D U P B 2
H46D H 0.793822 0.675754 -0.005706 0.114 Uiso 0.25 1 calc R U P B 2
H46E H 0.816017 0.785524 0.028196 0.114 Uiso 0.25 1 calc R U P B 2
H46F H 0.746450 0.706684 0.053273 0.114 Uiso 0.25 1 calc R U P B 2
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'
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
C28 N5 N6 117.3(2) . . ?
N8 N7 C28 117.2(2) . . ?
N3 N4 C15 116.6(2) . . ?
C29 N6 N5 117.3(2) . . ?
N7 N8 C29 117.7(2) . . ?
N1 N2 C15 117.8(2) . . ?
N4 N3 C14 117.0(2) . . ?
N2 N1 C14 116.6(2) . . ?
C1 N12 N11 118.2(2) . . ?
C42 N11 N12 116.7(2) . . ?
N10 N9 C42 117.5(2) . . ?
N9 N10 C1 117.2(2) . . ?
C22 C27 C28 124.2(2) . . ?
C26 C27 C22 117.6(2) . . ?
C26 C27 C28 118.2(2) . . ?
C27 C22 C21 123.8(2) . . ?
C23 C22 C27 118.5(2) . . ?
C23 C22 C21 117.4(2) . . ?
N5 C28 N7 125.2(2) . . ?
N5 C28 C27 118.5(2) . . ?
N7 C28 C27 116.2(2) . . ?
C7 C2 C1 126.3(2) . . ?
C3 C2 C7 117.9(2) . . ?
C3 C2 C1 115.7(2) . . ?
C36 C41 C42 122.4(2) . . ?
C40 C41 C42 119.5(2) . . ?
C40 C41 C36 118.1(2) . . ?
N11 C42 N9 123.2(2) . . ?
N11 C42 C41 118.8(2) . . ?
N9 C42 C41 117.8(2) . . ?
C2 C7 C8 124.7(2) . . ?
C6 C7 C2 118.7(3) . . ?
C6 C7 C8 116.5(2) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 C22 121.7(2) . . ?
C24 C23 H23 119.1 . . ?
C35 C30 C29 122.5(2) . . ?
C31 C30 C29 121.0(2) . . ?
C31 C30 C35 116.4(2) . . ?
C20 C21 C22 116.6(2) . . ?
C20 C21 C16 118.7(2) . . ?
C16 C21 C22 124.4(2) . . ?
N6 C29 N8 124.6(2) . . ?
N6 C29 C30 119.0(2) . . ?
N8 C29 C30 116.4(2) . . ?
C41 C36 C35 121.1(2) . . ?
C41 C36 C37 119.4(3) . . ?
C37 C36 C35 119.4(2) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 C21 121.7(2) . . ?
C19 C20 H20 119.1 . . ?
N12 C1 N10 122.7(2) . . ?
N12 C1 C2 119.5(2) . . ?
N10 C1 C2 117.8(2) . . ?
C21 C16 C15 123.9(2) . . ?
C17 C16 C21 117.1(2) . . ?
C17 C16 C15 118.9(2) . . ?
F4 C26 C27 117.6(2) . . ?
F4 C26 C25 117.9(2) . . ?
C25 C26 C27 124.3(2) . . ?
C13 C8 C7 123.4(2) . . ?
C9 C8 C7 117.2(3) . . ?
C9 C8 C13 119.2(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0(2) . . ?
C25 C24 H24 120.0 . . ?
C20 C19 H19 119.9 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C30 C35 C36 123.4(2) . . ?
C34 C35 C30 119.9(2) . . ?
C34 C35 C36 116.7(2) . . ?
N4 C15 C16 120.2(2) . . ?
N2 C15 N4 122.0(2) . . ?
N2 C15 C16 117.6(2) . . ?
F3 C17 C16 118.2(2) . . ?
F3 C17 C18 117.7(2) . . ?
C18 C17 C16 124.1(2) . . ?
F6 C40 C41 117.1(2) . . ?
F6 C40 C39 120.2(2) . . ?
C39 C40 C41 122.7(3) . . ?
C26 C25 C24 117.8(2) . . ?
C26 C25 H25 121.1 . . ?
C24 C25 H25 121.1 . . ?
F1 C3 C2 117.8(2) . . ?
F1 C3 C4 118.5(3) . . ?
C4 C3 C2 123.7(3) . . ?
N3 C14 C13 120.4(2) . . ?
N1 C14 N3 122.3(2) . . ?
N1 C14 C13 117.2(2) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 C19 118.1(3) . . ?
C17 C18 H18 120.9 . . ?
C8 C13 C14 121.8(2) . . ?
C12 C13 C8 117.4(3) . . ?
C12 C13 C14 120.6(3) . . ?
F5 C31 C30 119.1(2) . . ?
F5 C31 C32 117.1(2) . . ?
C32 C31 C30 123.8(2) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 C35 121.3(2) . . ?
C33 C34 H34 119.4 . . ?
C36 C37 H37 119.6 . . ?
C38 C37 C36 120.9(3) . . ?
C38 C37 H37 119.6 . . ?
C34 C33 H33 120.0 . . ?
C34 C33 C32 120.0(2) . . ?
C32 C33 H33 120.0 . . ?
C31 C32 C33 118.5(3) . . ?
C31 C32 H32 120.7 . . ?
C33 C32 H32 120.7 . . ?
C7 C6 H6 119.3 . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 119.3 . . ?
C40 C39 H39 120.8 . . ?
C38 C39 C40 118.4(3) . . ?
C38 C39 H39 120.8 . . ?
F2 C12 C13 119.3(3) . . ?
F2 C12 C11 117.3(3) . . ?
C11 C12 C13 123.3(3) . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.6(3) . . ?
C5 C4 H4 121.2 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C37 C38 C39 120.5(3) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C12 C11 H11 120.6 . . ?
C12 C11 C10 118.8(3) . . ?
C10 C11 H11 120.6 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C45 O1 C44 114.3(4) . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
O1 C45 C46 108.1(5) . . ?
O1 C45 H45 125.9 . . ?
C46 C45 H45 125.9 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C44 C43 H43A 109.5 . . ?
C44 C43 H43B 109.5 . . ?
C44 C43 H43C 109.5 . . ?
O1 C44 H44 121.4 . . ?
C43 C44 O1 117.2(6) . . ?
C43 C44 H44 121.4 . . ?
H43D C43B H43E 109.5 . . ?
H43D C43B H43F 109.5 . . ?
H43E C43B H43F 109.5 . . ?
C44B C43B H43D 109.5 . . ?
C44B C43B H43E 109.5 . . ?
C44B C43B H43F 109.5 . . ?
C43B C44B H44B 121.6 . . ?
C43B C44B O1B 116.9(18) . . ?
O1B C44B H44B 121.6 . . ?
C45B O1B C44B 107.5(13) . . ?
O1B C45B H45B 120.2 . . ?
O1B C45B C46B 119.5(17) . . ?
C46B C45B H45B 120.2 . . ?
C45B C46B H46D 109.5 . . ?
C45B C46B H46E 109.5 . . ?
C45B C46B H46F 109.5 . . ?
H46D C46B H46E 109.5 . . ?
H46D C46B H46F 109.5 . . ?
H46E C46B H46F 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
F4 C26 1.357(3) . ?
F1 C3 1.354(3) . ?
F3 C17 1.361(3) . ?
F6 C40 1.355(3) . ?
F5 C31 1.350(3) . ?
F2 C12 1.351(3) . ?
N5 N6 1.340(3) . ?
N5 C28 1.329(3) . ?
N7 N8 1.315(3) . ?
N7 C28 1.352(3) . ?
N4 N3 1.333(3) . ?
N4 C15 1.348(3) . ?
N6 C29 1.339(3) . ?
N8 C29 1.352(3) . ?
N2 N1 1.323(3) . ?
N2 C15 1.341(3) . ?
N3 C14 1.347(3) . ?
N1 C14 1.343(3) . ?
N12 N11 1.337(3) . ?
N12 C1 1.324(3) . ?
N11 C42 1.332(3) . ?
N9 N10 1.328(3) . ?
N9 C42 1.338(3) . ?
N10 C1 1.346(3) . ?
C27 C22 1.406(3) . ?
C27 C28 1.491(3) . ?
C27 C26 1.384(4) . ?
C22 C23 1.396(3) . ?
C22 C21 1.500(3) . ?
C2 C7 1.399(4) . ?
C2 C1 1.479(4) . ?
C2 C3 1.390(4) . ?
C41 C42 1.480(4) . ?
C41 C36 1.395(4) . ?
C41 C40 1.386(4) . ?
C7 C8 1.499(4) . ?
C7 C6 1.395(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(4) . ?
C30 C29 1.489(3) . ?
C30 C35 1.411(4) . ?
C30 C31 1.394(4) . ?
C21 C20 1.391(4) . ?
C21 C16 1.415(4) . ?
C36 C35 1.493(4) . ?
C36 C37 1.396(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.384(4) . ?
C16 C15 1.477(4) . ?
C16 C17 1.393(4) . ?
C26 C25 1.373(3) . ?
C8 C13 1.408(4) . ?
C8 C9 1.397(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.379(4) . ?
C19 H19 0.9500 . ?
C19 C18 1.379(4) . ?
C35 C34 1.393(3) . ?
C17 C18 1.369(4) . ?
C40 C39 1.383(4) . ?
C25 H25 0.9500 . ?
C3 C4 1.379(4) . ?
C14 C13 1.474(4) . ?
C18 H18 0.9500 . ?
C13 C12 1.396(4) . ?
C31 C32 1.375(4) . ?
C34 H34 0.9500 . ?
C34 C33 1.376(4) . ?
C37 H37 0.9500 . ?
C37 C38 1.377(4) . ?
C33 H33 0.9500 . ?
C33 C32 1.379(4) . ?
C32 H32 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.382(4) . ?
C39 H39 0.9500 . ?
C39 C38 1.377(4) . ?
C12 C11 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(4) . ?
C38 H38 0.9500 . ?
C5 H5 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.379(5) . ?
C10 H10 0.9500 . ?
O1 C45 1.358(6) . ?
O1 C44 1.419(6) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C46 C45 1.452(7) . ?
C45 H45 0.9500 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C43 C44 1.369(10) . ?
C44 H44 0.9500 . ?
C43B H43D 0.9800 . ?
C43B H43E 0.9800 . ?
C43B H43F 0.9800 . ?
C43B C44B 1.359(18) . ?
C44B H44B 0.9500 . ?
C44B O1B 1.365(15) . ?
O1B C45B 1.342(15) . ?
C45B H45B 0.9500 . ?
C45B C46B 1.359(16) . ?
C46B H46D 0.9800 . ?
C46B H46E 0.9800 . ?
C46B H46F 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
F4 C26 C25 C24 178.5(2) . . . . ?
F1 C3 C4 C5 179.6(2) . . . . ?
F3 C17 C18 C19 -178.3(2) . . . . ?
F6 C40 C39 C38 -177.3(2) . . . . ?
F5 C31 C32 C33 -178.5(2) . . . . ?
F2 C12 C11 C10 177.7(3) . . . . ?
N5 N6 C29 N8 -7.7(4) . . . . ?
N5 N6 C29 C30 172.4(2) . . . . ?
N7 N8 C29 N6 3.5(4) . . . . ?
N7 N8 C29 C30 -176.6(2) . . . . ?
N4 N3 C14 N1 22.9(3) . . . . ?
N4 N3 C14 C13 -159.9(2) . . . . ?
N6 N5 C28 N7 4.0(4) . . . . ?
N6 N5 C28 C27 -179.4(2) . . . . ?
N8 N7 C28 N5 -8.2(4) . . . . ?
N8 N7 C28 C27 175.1(2) . . . . ?
N2 N1 C14 N3 -23.1(3) . . . . ?
N2 N1 C14 C13 159.6(2) . . . . ?
N3 N4 C15 N2 -22.9(3) . . . . ?
N3 N4 C15 C16 162.7(2) . . . . ?
N3 C14 C13 C8 42.2(4) . . . . ?
N3 C14 C13 C12 -141.9(3) . . . . ?
N1 N2 C15 N4 22.8(3) . . . . ?
N1 N2 C15 C16 -162.6(2) . . . . ?
N1 C14 C13 C8 -140.5(3) . . . . ?
N1 C14 C13 C12 35.4(3) . . . . ?
N12 N11 C42 N9 -18.1(4) . . . . ?
N12 N11 C42 C41 165.6(2) . . . . ?
N11 N12 C1 N10 16.4(4) . . . . ?
N11 N12 C1 C2 -162.7(2) . . . . ?
N9 N10 C1 N12 -17.7(4) . . . . ?
N9 N10 C1 C2 161.3(2) . . . . ?
N10 N9 C42 N11 16.8(4) . . . . ?
N10 N9 C42 C41 -166.9(2) . . . . ?
C27 C22 C23 C24 0.3(4) . . . . ?
C27 C22 C21 C20 -104.5(3) . . . . ?
C27 C22 C21 C16 81.8(3) . . . . ?
C27 C26 C25 C24 2.0(4) . . . . ?
C22 C27 C28 N5 61.8(3) . . . . ?
C22 C27 C28 N7 -121.3(3) . . . . ?
C22 C27 C26 F4 -177.7(2) . . . . ?
C22 C27 C26 C25 -1.2(4) . . . . ?
C22 C23 C24 C25 0.5(4) . . . . ?
C22 C21 C20 C19 -176.1(2) . . . . ?
C22 C21 C16 C15 -5.0(4) . . . . ?
C22 C21 C16 C17 177.2(2) . . . . ?
C28 N5 N6 C29 3.8(3) . . . . ?
C28 N7 N8 C29 4.2(3) . . . . ?
C28 C27 C22 C23 179.3(2) . . . . ?
C28 C27 C22 C21 -6.3(4) . . . . ?
C28 C27 C26 F4 3.0(4) . . . . ?
C28 C27 C26 C25 179.5(3) . . . . ?
C2 C7 C8 C13 75.7(3) . . . . ?
C2 C7 C8 C9 -109.6(3) . . . . ?
C2 C7 C6 C5 -2.3(4) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C41 C36 C35 C30 -80.7(3) . . . . ?
C41 C36 C35 C34 100.0(3) . . . . ?
C41 C36 C37 C38 1.7(4) . . . . ?
C41 C40 C39 C38 1.2(4) . . . . ?
C42 N9 N10 C1 1.2(4) . . . . ?
C42 C41 C36 C35 -0.2(4) . . . . ?
C42 C41 C36 C37 175.9(2) . . . . ?
C42 C41 C40 F6 1.1(3) . . . . ?
C42 C41 C40 C39 -177.4(2) . . . . ?
C7 C2 C1 N12 -62.3(4) . . . . ?
C7 C2 C1 N10 118.6(3) . . . . ?
C7 C2 C3 F1 178.3(2) . . . . ?
C7 C2 C3 C4 -0.6(4) . . . . ?
C7 C8 C13 C14 -11.8(4) . . . . ?
C7 C8 C13 C12 172.2(2) . . . . ?
C7 C8 C9 C10 -174.7(2) . . . . ?
C7 C6 C5 C4 0.2(4) . . . . ?
C23 C22 C21 C20 70.0(3) . . . . ?
C23 C22 C21 C16 -103.7(3) . . . . ?
C23 C24 C25 C26 -1.6(4) . . . . ?
C30 C35 C34 C33 -0.9(4) . . . . ?
C30 C31 C32 C33 0.5(4) . . . . ?
C21 C22 C23 C24 -174.5(2) . . . . ?
C21 C20 C19 C18 -1.0(4) . . . . ?
C21 C16 C15 N4 140.1(2) . . . . ?
C21 C16 C15 N2 -34.6(3) . . . . ?
C21 C16 C17 F3 175.4(2) . . . . ?
C21 C16 C17 C18 -2.6(4) . . . . ?
C29 C30 C35 C36 6.9(4) . . . . ?
C29 C30 C35 C34 -173.9(2) . . . . ?
C29 C30 C31 F5 -7.0(4) . . . . ?
C29 C30 C31 C32 174.0(3) . . . . ?
C36 C41 C42 N11 88.9(3) . . . . ?
C36 C41 C42 N9 -87.6(3) . . . . ?
C36 C41 C40 F6 179.0(2) . . . . ?
C36 C41 C40 C39 0.5(4) . . . . ?
C36 C35 C34 C33 178.5(3) . . . . ?
C36 C37 C38 C39 0.1(4) . . . . ?
C20 C21 C16 C15 -178.6(2) . . . . ?
C20 C21 C16 C17 3.7(3) . . . . ?
C20 C19 C18 C17 2.1(4) . . . . ?
C1 N12 N11 C42 1.4(4) . . . . ?
C1 C2 C7 C8 -3.3(4) . . . . ?
C1 C2 C7 C6 -178.8(2) . . . . ?
C1 C2 C3 F1 -0.6(3) . . . . ?
C1 C2 C3 C4 -179.5(2) . . . . ?
C16 C21 C20 C19 -2.0(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C26 C27 C22 C23 0.0(4) . . . . ?
C26 C27 C22 C21 174.4(2) . . . . ?
C26 C27 C28 N5 -118.9(3) . . . . ?
C26 C27 C28 N7 58.0(3) . . . . ?
C8 C7 C6 C5 -178.1(2) . . . . ?
C8 C13 C12 F2 -175.4(2) . . . . ?
C8 C13 C12 C11 2.5(4) . . . . ?
C8 C9 C10 C11 2.1(4) . . . . ?
C35 C30 C29 N6 -34.5(4) . . . . ?
C35 C30 C29 N8 145.6(2) . . . . ?
C35 C30 C31 F5 175.9(2) . . . . ?
C35 C30 C31 C32 -3.1(4) . . . . ?
C35 C36 C37 C38 177.9(2) . . . . ?
C35 C34 C33 C32 -1.9(4) . . . . ?
C15 N4 N3 C14 0.2(3) . . . . ?
C15 N2 N1 C14 0.2(3) . . . . ?
C15 C16 C17 F3 -2.4(3) . . . . ?
C15 C16 C17 C18 179.5(2) . . . . ?
C17 C16 C15 N4 -42.2(3) . . . . ?
C17 C16 C15 N2 143.1(2) . . . . ?
C40 C41 C42 N11 -93.3(3) . . . . ?
C40 C41 C42 N9 90.2(3) . . . . ?
C40 C41 C36 C35 -178.1(2) . . . . ?
C40 C41 C36 C37 -1.9(4) . . . . ?
C40 C39 C38 C37 -1.5(4) . . . . ?
C3 C2 C7 C8 177.9(2) . . . . ?
C3 C2 C7 C6 2.4(4) . . . . ?
C3 C2 C1 N12 116.5(3) . . . . ?
C3 C2 C1 N10 -62.6(3) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C14 C13 C12 F2 8.5(4) . . . . ?
C14 C13 C12 C11 -173.6(3) . . . . ?
C13 C8 C9 C10 0.2(4) . . . . ?
C13 C12 C11 C10 -0.2(4) . . . . ?
C31 C30 C29 N6 148.5(3) . . . . ?
C31 C30 C29 N8 -31.3(4) . . . . ?
C31 C30 C35 C36 -176.0(2) . . . . ?
C31 C30 C35 C34 3.2(4) . . . . ?
C34 C33 C32 C31 2.1(4) . . . . ?
C37 C36 C35 C30 103.1(3) . . . . ?
C37 C36 C35 C34 -76.2(3) . . . . ?
C6 C7 C8 C13 -108.8(3) . . . . ?
C6 C7 C8 C9 65.9(3) . . . . ?
C12 C11 C10 C9 -2.1(4) . . . . ?
C9 C8 C13 C14 173.6(2) . . . . ?
C9 C8 C13 C12 -2.4(4) . . . . ?
C45 O1 C44 C43 84.1(7) . . . . ?
C44 O1 C45 C46 -171.0(5) . . . . ?
C43B C44B O1B C45B -168.0(19) . . . . ?
C44B O1B C45B C46B -172.8(18) . . . . ?
