#------------------------------------------------------------------------------
#$Date: 2022-10-26 01:18:14 +0300 (Wed, 26 Oct 2022) $
#$Revision: 278782 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/78/1567849.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_1567849
loop_
_publ_author_name
'Tilly, David P.'
'Žabka, Matej'
'Vitorica-Yrzebal, Inigo'
'Sparkes, Hazel Anne'
'Pridmore, Natalie E.'
'Clayden, Jonathan'
_publ_section_title
;
 Supramolecular interactions between ethylene-bridged oligoureas:
 nanorings and chains formed by cooperative positive allostery
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04716K
_journal_year                    2022
_chemical_formula_moiety         'C23 H26 F6 N4 O2'
_chemical_formula_sum            'C23 H26 F6 N4 O2'
_chemical_formula_weight         504.48
_chemical_melting_point          422
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.3610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   18.0463(4)
_cell_length_b                   21.9267(6)
_cell_length_c                   18.6546(5)
_cell_measurement_reflns_used    8952
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.32
_cell_volume                     7117.8(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            64703
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.937
_diffrn_reflns_theta_min         1.464
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0851 before and 0.0588 after correction. The Ratio of minimum to maximum transmission is 0.7409. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             3144
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.474
_exptl_crystal_size_mid          0.426
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1015
_refine_ls_number_reflns         17042
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0533
_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)+(0.0495P)²+4.5874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10765
_reflns_number_total             17042
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           testm1_CCDC1
_cod_database_code               1567849
_shelx_shelxl_version_number     2017/1
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N10-C53 \\sim N10A-C53
 with sigma of 0.01
 N10A-C54A \\sim N10-C54
 with sigma of 0.01
 C55A-C54A \\sim C55-C54
 with sigma of 0.01
 N11-C55A \\sim N11-C55
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N10 \\sim C54 \\sim C55 \\sim C55A \\sim C54A \\sim N10A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C55A)=Sof(H55C)=Sof(H55D)=Sof(C54A)=Sof(H54C)=Sof(H54D)=Sof(N10A)=
 Sof(H10A)=1-FVAR(1)
 Sof(N10)=Sof(H10)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C55)=Sof(H55A)=Sof(H55B)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10B,H10C), C11(H11A,H11B), C17(H17A,H17B), C32(H32A,H32B), C33(H33A,
 H33B), C39(H39A,H39B), C54(H54A,H54B), C55(H55A,H55B), C61(H61A,H61B),
 C55A(H55C,H55D), C54A(H54C,H54D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C5(H5), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C26(H26), C28(H28), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45),
  N10(H10), C46(H46), C48(H48), C50(H50), C63(H63), C64(H64), C65(H65),
 C66(H66), C67(H67), N10A(H10A)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C58(H58A,H58B,H58C), C59(H59A,
 H59B,H59C), C60(H60A,H60B,H60C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_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
F1 F 0.17711(10) 0.39608(7) -0.35486(8) 0.0484(4) Uani 1 1 d . . . . .
F2 F 0.25832(11) 0.34559(7) -0.27143(8) 0.0553(5) Uani 1 1 d . . . . .
F3 F 0.29541(11) 0.39417(8) -0.35467(10) 0.0596(5) Uani 1 1 d . . . . .
F4 F 0.17915(9) 0.62289(7) -0.34476(8) 0.0407(4) Uani 1 1 d . . . . .
F5 F 0.29943(9) 0.64269(8) -0.30807(11) 0.0609(5) Uani 1 1 d . . . . .
F6 F 0.22603(12) 0.66433(7) -0.23952(9) 0.0577(5) Uani 1 1 d . . . . .
O1 O 0.39420(9) 0.59183(7) -0.04116(8) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.49722(9) 0.76526(6) 0.15016(8) 0.0233(3) Uani 1 1 d . . . . .
N1 N 0.35130(11) 0.49332(8) -0.06692(9) 0.0200(4) Uani 1 1 d . . . . .
N2 N 0.43051(11) 0.51918(8) 0.04721(10) 0.0227(4) Uani 1 1 d . . . . .
N3 N 0.47944(11) 0.66300(8) 0.15643(9) 0.0233(4) Uani 1 1 d . . . . .
N4 N 0.44247(11) 0.71292(8) 0.04339(10) 0.0208(4) Uani 1 1 d . . . . .
C1 C 0.29934(13) 0.44830(10) -0.18681(11) 0.0230(5) Uani 1 1 d . . . . .
H1A H 0.314325 0.409399 -0.165459 0.028 Uiso 1 1 calc R . . . .
C2 C 0.26282(13) 0.45318(10) -0.26192(12) 0.0249(5) Uani 1 1 d . . . . .
C3 C 0.24101(13) 0.50932(11) -0.29506(12) 0.0255(5) Uani 1 1 d . . . . .
H3 H 0.216669 0.512372 -0.346742 0.031 Uiso 1 1 calc R . . . .
C4 C 0.25576(13) 0.56076(10) -0.25057(12) 0.0223(5) Uani 1 1 d . . . . .
C5 C 0.29102(12) 0.55732(10) -0.17495(11) 0.0203(4) Uani 1 1 d . . . . .
H5 H 0.299437 0.593221 -0.145392 0.024 Uiso 1 1 calc R . . . .
C6 C 0.31410(12) 0.50040(10) -0.14260(11) 0.0198(4) Uani 1 1 d . . . . .
C7 C 0.24860(16) 0.39708(11) -0.31006(13) 0.0343(6) Uani 1 1 d . . . . .
C8 C 0.23909(14) 0.62227(11) -0.28530(13) 0.0297(5) Uani 1 1 d . . . . .
C9 C 0.39226(13) 0.53850(10) -0.02134(11) 0.0194(4) Uani 1 1 d . . . . .
C10 C 0.48029(13) 0.56271(10) 0.09628(12) 0.0244(5) Uani 1 1 d . . . . .
H10B H 0.511515 0.584752 0.068266 0.029 Uiso 1 1 calc R . . . .
H10C H 0.515846 0.540479 0.137536 0.029 Uiso 1 1 calc R . . . .
C11 C 0.43409(14) 0.60854(10) 0.12812(12) 0.0239(5) Uani 1 1 d . . . . .
H11A H 0.387738 0.620592 0.088923 0.029 Uiso 1 1 calc R . . . .
H11B H 0.417010 0.589150 0.168942 0.029 Uiso 1 1 calc R . . . .
C12 C 0.47368(13) 0.71662(10) 0.11737(11) 0.0206(5) Uani 1 1 d . . . . .
C13 C 0.41454(13) 0.76588(9) -0.00598(11) 0.0210(5) Uani 1 1 d . . . . .
C14 C 0.37944(15) 0.73927(10) -0.08323(12) 0.0285(5) Uani 1 1 d . . . . .
H14A H 0.418712 0.716261 -0.099361 0.043 Uiso 1 1 calc GR . . . .
H14B H 0.360173 0.772444 -0.118432 0.043 Uiso 1 1 calc GR . . . .
H14C H 0.336916 0.712026 -0.081430 0.043 Uiso 1 1 calc GR . . . .
C15 C 0.48037(14) 0.80861(10) -0.00912(12) 0.0272(5) Uani 1 1 d . . . . .
H15A H 0.504715 0.824077 0.040859 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.460273 0.842872 -0.042313 0.041 Uiso 1 1 calc GR . . . .
H15C H 0.518386 0.786307 -0.027928 0.041 Uiso 1 1 calc GR . . . .
C16 C 0.35249(14) 0.79946(11) 0.02072(13) 0.0287(5) Uani 1 1 d . . . . .
H16A H 0.310102 0.771427 0.020356 0.043 Uiso 1 1 calc GR . . . .
H16B H 0.333227 0.833912 -0.012447 0.043 Uiso 1 1 calc GR . . . .
H16C H 0.374400 0.814555 0.071362 0.043 Uiso 1 1 calc GR . . . .
C17 C 0.51829(14) 0.66339(10) 0.23559(11) 0.0234(5) Uani 1 1 d . . . . .
H17A H 0.560997 0.693188 0.244729 0.028 Uiso 1 1 calc R . . . .
H17B H 0.540889 0.622606 0.249960 0.028 Uiso 1 1 calc R . . . .
C18 C 0.46632(14) 0.67935(10) 0.28455(12) 0.0253(5) Uani 1 1 d . . . . .
C19 C 0.39874(15) 0.71189(12) 0.25846(14) 0.0345(6) Uani 1 1 d . . . . .
H19 H 0.383516 0.724010 0.207772 0.041 Uiso 1 1 calc R . . . .
C20 C 0.35266(18) 0.72720(14) 0.30493(17) 0.0474(7) Uani 1 1 d . . . . .
H20 H 0.307052 0.750243 0.286153 0.057 Uiso 1 1 calc R . . . .
C21 C 0.37314(19) 0.70902(14) 0.37769(17) 0.0491(8) Uani 1 1 d . . . . .
H21 H 0.341740 0.719472 0.409452 0.059 Uiso 1 1 calc R . . . .
C22 C 0.43900(18) 0.67569(12) 0.40486(14) 0.0411(7) Uani 1 1 d . . . . .
H22 H 0.452366 0.662316 0.455089 0.049 Uiso 1 1 calc R . . . .
C23 C 0.48657(16) 0.66129(11) 0.35893(12) 0.0318(6) Uani 1 1 d . . . . .
H23 H 0.532772 0.639152 0.378468 0.038 Uiso 1 1 calc R . . . .
F7 F 0.27063(9) -0.12104(7) 0.26683(10) 0.0471(4) Uani 1 1 d . . . . .
F8 F 0.38740(9) -0.09211(6) 0.28992(8) 0.0392(4) Uani 1 1 d . . . . .
F9 F 0.33757(10) -0.14181(6) 0.19051(8) 0.0452(4) Uani 1 1 d . . . . .
F10 F 0.08883(9) 0.01679(10) 0.01945(9) 0.0576(5) Uani 1 1 d . . . . .
F11 F 0.16104(11) -0.04297(8) -0.02074(8) 0.0550(5) Uani 1 1 d . . . . .
F12 F 0.17146(10) 0.05312(8) -0.03090(8) 0.0512(5) Uani 1 1 d . . . . .
O3 O 0.31731(9) 0.18310(7) 0.13003(8) 0.0232(3) Uani 1 1 d . . . . .
O4 O 0.40101(9) 0.38653(6) 0.03029(8) 0.0209(3) Uani 1 1 d . . . . .
N5 N 0.31387(12) 0.12463(8) 0.23098(10) 0.0235(4) Uani 1 1 d . . . . .
N6 N 0.35498(11) 0.22398(8) 0.24551(10) 0.0223(4) Uani 1 1 d . . . . .
N7 N 0.44517(10) 0.33344(7) 0.13801(9) 0.0175(4) Uani 1 1 d . . . . .
N8 N 0.35053(10) 0.29227(8) 0.04081(9) 0.0179(4) Uani 1 1 d . . . . .
C01A C 0.29071(13) 0.06962(10) 0.19340(11) 0.0208(5) Uani 1 1 d . . . . .
C24 C 0.31896(13) 0.01514(10) 0.22879(11) 0.0202(4) Uani 1 1 d . . . . .
H24 H 0.354057 0.016115 0.276773 0.024 Uiso 1 1 calc R . . . .
C25 C 0.29629(13) -0.04035(10) 0.19459(12) 0.0210(5) Uani 1 1 d . . . . .
C26 C 0.24607(13) -0.04257(10) 0.12414(12) 0.0231(5) Uani 1 1 d . . . . .
H26 H 0.231273 -0.080633 0.100306 0.028 Uiso 1 1 calc R . . . .
C27 C 0.21784(13) 0.01128(10) 0.08908(12) 0.0227(5) Uani 1 1 d . . . . .
C28 C 0.23918(13) 0.06761(10) 0.12281(12) 0.0215(5) Uani 1 1 d . . . . .
H28 H 0.218914 0.104245 0.098077 0.026 Uiso 1 1 calc R . . . .
C29 C 0.32311(14) -0.09867(10) 0.23483(13) 0.0255(5) Uani 1 1 d . . . . .
C30 C 0.16047(14) 0.01002(11) 0.01426(13) 0.0287(5) Uani 1 1 d . . . . .
C31 C 0.32784(13) 0.17766(9) 0.19782(11) 0.0202(5) Uani 1 1 d . . . . .
C32 C 0.37056(13) 0.28314(9) 0.21719(11) 0.0206(5) Uani 1 1 d . . . . .
H32A H 0.379716 0.313480 0.257905 0.025 Uiso 1 1 calc R . . . .
H32B H 0.324992 0.296456 0.177858 0.025 Uiso 1 1 calc R . . . .
C33 C 0.44068(12) 0.28115(9) 0.18530(11) 0.0190(4) Uani 1 1 d . . . . .
H33A H 0.487934 0.279695 0.226908 0.023 Uiso 1 1 calc R . . . .
H33B H 0.438630 0.243266 0.155957 0.023 Uiso 1 1 calc R . . . .
C34 C 0.39846(12) 0.33969(9) 0.06712(11) 0.0174(4) Uani 1 1 d . . . . .
C35 C 0.29702(12) 0.28974(9) -0.03448(11) 0.0193(4) Uani 1 1 d . . . . .
C36 C 0.23770(13) 0.34074(10) -0.04418(13) 0.0271(5) Uani 1 1 d . . . . .
H36A H 0.208656 0.336293 -0.006918 0.041 Uiso 1 1 calc GR . . . .
H36B H 0.202411 0.338399 -0.094072 0.041 Uiso 1 1 calc GR . . . .
H36C H 0.263921 0.380292 -0.037780 0.041 Uiso 1 1 calc GR . . . .
C37 C 0.25612(13) 0.22803(10) -0.03909(12) 0.0240(5) Uani 1 1 d . . . . .
H37A H 0.294286 0.195177 -0.029924 0.036 Uiso 1 1 calc GR . . . .
H37B H 0.220881 0.223072 -0.088681 0.036 Uiso 1 1 calc GR . . . .
H37C H 0.227025 0.226401 -0.001601 0.036 Uiso 1 1 calc GR . . . .
C38 C 0.34147(14) 0.29151(10) -0.09336(11) 0.0254(5) Uani 1 1 d . . . . .
H38A H 0.372196 0.328923 -0.087606 0.038 Uiso 1 1 calc GR . . . .
H38B H 0.305322 0.290755 -0.142891 0.038 Uiso 1 1 calc GR . . . .
H38C H 0.375521 0.255988 -0.087465 0.038 Uiso 1 1 calc GR . . . .
C39 C 0.50362(12) 0.37988(9) 0.16636(11) 0.0194(4) Uani 1 1 d . . . . .
H39A H 0.516069 0.400248 0.123636 0.023 Uiso 1 1 calc R . . . .
H39B H 0.550914 0.359471 0.195647 0.023 Uiso 1 1 calc R . . . .
C40 C 0.48070(12) 0.42807(9) 0.21455(11) 0.0167(4) Uani 1 1 d . . . . .
C41 C 0.53812(13) 0.46133(9) 0.26400(11) 0.0197(4) Uani 1 1 d . . . . .
H41 H 0.590558 0.453591 0.266576 0.024 Uiso 1 1 calc R . . . .
C42 C 0.51941(13) 0.50546(9) 0.30931(11) 0.0221(5) Uani 1 1 d . . . . .
H42 H 0.558949 0.527823 0.342723 0.027 Uiso 1 1 calc R . . . .
C43 C 0.44299(14) 0.51710(10) 0.30602(12) 0.0236(5) Uani 1 1 d . . . . .
H43 H 0.430101 0.546890 0.337682 0.028 Uiso 1 1 calc R . . . .
C44 C 0.38563(14) 0.48501(9) 0.25628(12) 0.0222(5) Uani 1 1 d . . . . .
H44 H 0.333243 0.493289 0.253366 0.027 Uiso 1 1 calc R . . . .
C45 C 0.40429(12) 0.44077(9) 0.21062(11) 0.0187(4) Uani 1 1 d . . . . .
H45 H 0.364582 0.419089 0.176532 0.022 Uiso 1 1 calc R . . . .
F13 F 0.57533(9) -0.02365(10) 1.03469(8) 0.0626(6) Uani 1 1 d . . . . .
F14 F 0.66425(9) 0.02663(7) 1.00459(8) 0.0438(4) Uani 1 1 d . . . . .
F15 F 0.65853(8) -0.07014(7) 0.99295(8) 0.0390(4) Uani 1 1 d . . . . .
F16 F 0.45752(11) -0.16255(6) 0.78761(10) 0.0607(5) Uani 1 1 d . . . . .
F17 F 0.49859(11) -0.12356(8) 0.70018(11) 0.0640(5) Uani 1 1 d . . . . .
F18 F 0.38471(9) -0.10451(6) 0.70794(9) 0.0443(4) Uani 1 1 d . . . . .
O5 O 0.40095(11) 0.08987(7) 0.66385(8) 0.0369(5) Uani 1 1 d . . . . .
O6 O 0.32303(10) 0.15004(8) 0.38565(8) 0.0309(4) Uani 1 1 d . . . . .
N9 N 0.47110(11) 0.11075(8) 0.78280(10) 0.0207(4) Uani 1 1 d . . . . .
N10 N 0.42192(17) 0.18868(11) 0.70261(14) 0.0232(6) Uani 0.786(4) 1 d D U P A 1
H10 H 0.444127 0.214311 0.738101 0.028 Uiso 0.786(4) 1 calc R . P A 1
N11 N 0.35941(14) 0.20200(9) 0.49487(10) 0.0337(5) Uani 1 1 d D . . . .
N12 N 0.34493(13) 0.09718(9) 0.49515(11) 0.0295(5) Uani 1 1 d . . . . .
C019 C 0.49130(12) 0.05166(9) 0.80868(11) 0.0186(4) Uani 1 1 d . . . . .
C46 C 0.54206(13) 0.04443(10) 0.87912(11) 0.0205(5) Uani 1 1 d . . . . .
H46 H 0.561456 0.079353 0.908192 0.025 Uiso 1 1 calc R . . . .
C47 C 0.56432(13) -0.01326(10) 0.90690(11) 0.0215(5) Uani 1 1 d . . . . .
C48 C 0.53797(13) -0.06530(10) 0.86538(12) 0.0235(5) Uani 1 1 d . . . . .
H48 H 0.554310 -0.104786 0.883959 0.028 Uiso 1 1 calc R . . . .
C49 C 0.48707(13) -0.05755(10) 0.79599(12) 0.0238(5) Uani 1 1 d . . . . .
C50 C 0.46297(13) -0.00015(10) 0.76725(12) 0.0230(5) Uani 1 1 d . . . . .
H50 H 0.427463 0.003661 0.719731 0.028 Uiso 1 1 calc R . . . .
C51 C 0.61506(14) -0.02022(11) 0.98426(12) 0.0280(5) Uani 1 1 d . . . . .
C52 C 0.45724(15) -0.11173(11) 0.74837(15) 0.0341(6) Uani 1 1 d . . . . .
C53 C 0.43122(15) 0.12692(11) 0.71236(12) 0.0310(6) Uani 1 1 d D . . . .
C54 C 0.37428(17) 0.21045(13) 0.63189(14) 0.0232(7) Uani 0.786(4) 1 d D U P A 1
H54A H 0.362422 0.254175 0.636159 0.028 Uiso 0.786(4) 1 calc R . P A 1
H54B H 0.325174 0.187658 0.618797 0.028 Uiso 0.786(4) 1 calc R . P A 1
C55 C 0.41521(18) 0.20211(13) 0.57076(15) 0.0224(7) Uani 0.786(4) 1 d D U P A 1
H55A H 0.452773 0.235532 0.573663 0.027 Uiso 0.786(4) 1 calc R . P A 1
H55B H 0.443843 0.163100 0.578593 0.027 Uiso 0.786(4) 1 calc R . P A 1
C56 C 0.34136(14) 0.14901(11) 0.45481(12) 0.0277(5) Uani 1 1 d . . . . .
C57 C 0.34726(14) 0.03522(10) 0.46501(12) 0.0268(5) Uani 1 1 d . . . . .
C58 C 0.36056(17) -0.00835(11) 0.53074(14) 0.0354(6) Uani 1 1 d . . . . .
H58A H 0.409340 0.001614 0.566740 0.053 Uiso 1 1 calc GR . . . .
H58B H 0.362447 -0.050324 0.513260 0.053 Uiso 1 1 calc GR . . . .
H58C H 0.318459 -0.004388 0.554527 0.053 Uiso 1 1 calc GR . . . .
C59 C 0.41492(14) 0.03118(12) 0.43003(13) 0.0317(6) Uani 1 1 d . . . . .
H59A H 0.407989 0.061110 0.389778 0.048 Uiso 1 1 calc GR . . . .
H59B H 0.417161 -0.009898 0.410024 0.048 Uiso 1 1 calc GR . . . .
H59C H 0.462901 0.039756 0.467926 0.048 Uiso 1 1 calc GR . . . .
C60 C 0.27097(15) 0.01988(12) 0.40883(14) 0.0353(6) Uani 1 1 d . . . . .
H60A H 0.229264 0.021874 0.433366 0.053 Uiso 1 1 calc GR . . . .
H60B H 0.273619 -0.021336 0.389343 0.053 Uiso 1 1 calc GR . . . .
H60C H 0.261187 0.049277 0.367823 0.053 Uiso 1 1 calc GR . . . .
C61 C 0.34896(15) 0.25942(11) 0.45401(13) 0.0286(5) Uani 1 1 d . . . . .
H61A H 0.335020 0.291461 0.485489 0.034 Uiso 1 1 calc R . . . .
H61B H 0.305414 0.254949 0.409105 0.034 Uiso 1 1 calc R . . . .
C62 C 0.41874(13) 0.28023(10) 0.43050(11) 0.0231(5) Uani 1 1 d . . . . .
C63 C 0.47566(13) 0.24126(10) 0.42126(12) 0.0256(5) Uani 1 1 d . . . . .
H63 H 0.471728 0.198896 0.430281 0.031 Uiso 1 1 calc R . . . .
C64 C 0.53830(14) 0.26269(12) 0.39913(13) 0.0328(6) Uani 1 1 d . . . . .
H64 H 0.576773 0.235076 0.393094 0.039 Uiso 1 1 calc R . . . .
C65 C 0.54496(15) 0.32404(12) 0.38582(13) 0.0327(6) Uani 1 1 d . . . . .
H65 H 0.588074 0.338915 0.370967 0.039 Uiso 1 1 calc R . . . .
C66 C 0.48874(15) 0.36343(12) 0.39422(13) 0.0321(6) Uani 1 1 d . . . . .
H66 H 0.492861 0.405662 0.384571 0.039 Uiso 1 1 calc R . . . .
C67 C 0.42641(15) 0.34241(11) 0.41649(13) 0.0308(6) Uani 1 1 d . . . . .
H67 H 0.388219 0.370339 0.422413 0.037 Uiso 1 1 calc R . . . .
C55A C 0.3587(6) 0.2065(5) 0.5737(4) 0.028(2) Uani 0.214(4) 1 d D U P A 2
H55C H 0.326307 0.174550 0.587637 0.033 Uiso 0.214(4) 1 calc R . P A 2
H55D H 0.341996 0.247193 0.586118 0.033 Uiso 0.214(4) 1 calc R . P A 2
C54A C 0.4442(6) 0.1956(5) 0.6090(5) 0.023(2) Uani 0.214(4) 1 d D U P A 2
H54C H 0.462418 0.161897 0.582645 0.028 Uiso 0.214(4) 1 calc R . P A 2
H54D H 0.473451 0.232754 0.603805 0.028 Uiso 0.214(4) 1 calc R . P A 2
N10A N 0.4582(6) 0.1802(4) 0.6873(4) 0.0195(19) Uani 0.214(4) 1 d D U P A 2
H10A H 0.485015 0.205827 0.720449 0.023 Uiso 0.214(4) 1 calc R . P A 2
H2 H 0.4285(14) 0.4814(12) 0.0586(14) 0.030(7) Uiso 1 1 d . . . . .
H1 H 0.3589(15) 0.4558(12) -0.0486(14) 0.034(7) Uiso 1 1 d . . . . .
H9 H 0.4880(13) 0.1393(11) 0.8114(13) 0.020(6) Uiso 1 1 d . . . . .
H12 H 0.3606(17) 0.0989(13) 0.5454(17) 0.048(8) Uiso 1 1 d . . . . .
H4 H 0.4328(15) 0.6807(12) 0.0236(14) 0.027(7) Uiso 1 1 d . . . . .
H6 H 0.3646(16) 0.2187(12) 0.2900(16) 0.038(8) Uiso 1 1 d . . . . .
H5A H 0.3217(16) 0.1264(13) 0.2773(16) 0.042(8) Uiso 1 1 d . . . . .
H8 H 0.3490(15) 0.2617(12) 0.0704(14) 0.033(7) 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'
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
C6 N1 H1 118.3(17) . . ?
C9 N1 C6 125.06(18) . . ?
C9 N1 H1 115.1(17) . . ?
C9 N2 C10 117.72(18) . . ?
C9 N2 H2 119.5(17) . . ?
C10 N2 H2 122.4(17) . . ?
C12 N3 C11 123.39(17) . . ?
C12 N3 C17 118.76(17) . . ?
C17 N3 C11 116.30(17) . . ?
C12 N4 C13 124.68(18) . . ?
C12 N4 H4 120.7(18) . . ?
C13 N4 H4 114.2(18) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 C6 120.1(2) . . ?
C6 C1 H1A 120.0 . . ?
C1 C2 C3 121.5(2) . . ?
C1 C2 C7 120.1(2) . . ?
C3 C2 C7 118.44(19) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 C8 119.46(19) . . ?
C5 C4 C8 118.4(2) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 N1 118.10(19) . . ?
C1 C6 C5 119.16(19) . . ?
C5 C6 N1 122.74(19) . . ?
F1 C7 C2 111.7(2) . . ?
F2 C7 F1 107.0(2) . . ?
F2 C7 F3 106.5(2) . . ?
F2 C7 C2 113.25(19) . . ?
F3 C7 F1 105.93(19) . . ?
F3 C7 C2 112.0(2) . . ?
F4 C8 F5 106.32(19) . . ?
F4 C8 C4 113.4(2) . . ?
F5 C8 C4 110.5(2) . . ?
F6 C8 F4 106.7(2) . . ?
F6 C8 F5 105.7(2) . . ?
F6 C8 C4 113.63(19) . . ?
O1 C9 N1 123.28(19) . . ?
O1 C9 N2 122.33(19) . . ?
N2 C9 N1 114.39(18) . . ?
N2 C10 H10B 109.3 . . ?
N2 C10 H10C 109.3 . . ?
N2 C10 C11 111.55(19) . . ?
H10B C10 H10C 108.0 . . ?
C11 C10 H10B 109.3 . . ?
C11 C10 H10C 109.3 . . ?
N3 C11 C10 111.54(19) . . ?
N3 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O2 C12 N3 120.29(18) . . ?
O2 C12 N4 123.33(19) . . ?
N4 C12 N3 116.38(18) . . ?
N4 C13 C14 105.90(17) . . ?
N4 C13 C15 111.36(18) . . ?
N4 C13 C16 109.38(17) . . ?
C14 C13 C16 109.55(19) . . ?
C15 C13 C14 109.31(18) . . ?
C15 C13 C16 111.19(18) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 108.8 . . ?
N3 C17 H17B 108.8 . . ?
N3 C17 C18 113.84(19) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C19 C18 C17 122.4(2) . . ?
C19 C18 C23 118.0(2) . . ?
C23 C18 C17 119.6(2) . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.2(3) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C01A N5 H5A 120(2) . . ?
C31 N5 C01A 124.75(18) . . ?
C31 N5 H5A 115(2) . . ?
C31 N6 C32 120.07(18) . . ?
C31 N6 H6 121(2) . . ?
C32 N6 H6 119(2) . . ?
C34 N7 C33 122.75(17) . . ?
C34 N7 C39 118.63(17) . . ?
C39 N7 C33 118.58(16) . . ?
C34 N8 C35 124.38(17) . . ?
C34 N8 H8 118.8(17) . . ?
C35 N8 H8 116.7(17) . . ?
C24 C01A N5 118.50(19) . . ?
C24 C01A C28 119.2(2) . . ?
C28 C01A N5 122.3(2) . . ?
C01A C24 H24 119.7 . . ?
C25 C24 C01A 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 C29 120.20(19) . . ?
C26 C25 C29 119.3(2) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 C25 119.1(2) . . ?
C27 C26 H26 120.5 . . ?
C26 C27 C28 121.4(2) . . ?
C26 C27 C30 120.1(2) . . ?
C28 C27 C30 118.4(2) . . ?
C01A C28 H28 120.4 . . ?
C27 C28 C01A 119.3(2) . . ?
C27 C28 H28 120.4 . . ?
F7 C29 C25 111.32(19) . . ?
F8 C29 F7 105.58(18) . . ?
F8 C29 C25 113.12(18) . . ?
F9 C29 F7 107.19(19) . . ?
F9 C29 F8 106.35(19) . . ?
F9 C29 C25 112.79(19) . . ?
F10 C30 F11 105.5(2) . . ?
F10 C30 C27 112.0(2) . . ?
F11 C30 C27 112.2(2) . . ?
F12 C30 F10 106.3(2) . . ?
F12 C30 F11 106.9(2) . . ?
F12 C30 C27 113.46(19) . . ?
O3 C31 N5 123.20(19) . . ?
O3 C31 N6 122.13(19) . . ?
N6 C31 N5 114.67(18) . . ?
N6 C32 H32A 109.2 . . ?
N6 C32 H32B 109.2 . . ?
N6 C32 C33 111.93(18) . . ?
H32A C32 H32B 107.9 . . ?
C33 C32 H32A 109.2 . . ?
C33 C32 H32B 109.2 . . ?
N7 C33 C32 113.24(17) . . ?
N7 C33 H33A 108.9 . . ?
N7 C33 H33B 108.9 . . ?
C32 C33 H33A 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
O4 C34 N7 120.74(18) . . ?
O4 C34 N8 123.08(18) . . ?
N8 C34 N7 116.18(18) . . ?
N8 C35 C36 110.25(17) . . ?
N8 C35 C37 105.66(16) . . ?
N8 C35 C38 110.34(18) . . ?
C36 C35 C37 109.15(19) . . ?
C38 C35 C36 112.52(18) . . ?
C38 C35 C37 108.67(18) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N7 C39 H39A 108.6 . . ?
N7 C39 H39B 108.6 . . ?
N7 C39 C40 114.63(18) . . ?
H39A C39 H39B 107.6 . . ?
C40 C39 H39A 108.6 . . ?
C40 C39 H39B 108.6 . . ?
C41 C40 C39 119.02(19) . . ?
C45 C40 C39 122.13(18) . . ?
C45 C40 C41 118.85(19) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 C40 120.7(2) . . ?
C42 C41 H41 119.7 . . ?
C41 C42 H42 119.9 . . ?
C41 C42 C43 120.1(2) . . ?
C43 C42 H42 119.9 . . ?
C42 C43 H43 120.2 . . ?
C44 C43 C42 119.6(2) . . ?
C44 C43 H43 120.2 . . ?
C43 C44 H44 119.8 . . ?
C43 C44 C45 120.4(2) . . ?
C45 C44 H44 119.8 . . ?
C40 C45 C44 120.4(2) . . ?
C40 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C019 N9 H9 117.5(16) . . ?
C53 N9 C019 126.54(19) . . ?
C53 N9 H9 115.7(16) . . ?
C53 N10 H10 121.0 . . ?
C53 N10 C54 117.9(2) . . ?
C54 N10 H10 121.0 . . ?
C56 N11 C55 121.1(2) . . ?
C56 N11 C61 117.84(19) . . ?
C56 N11 C55A 122.3(5) . . ?
C61 N11 C55 116.9(2) . . ?
C61 N11 C55A 115.4(5) . . ?
C56 N12 C57 124.24(19) . . ?
C56 N12 H12 119.7(19) . . ?
C57 N12 H12 113.6(19) . . ?
N9 C019 C46 118.44(19) . . ?
C50 C019 N9 122.75(19) . . ?
C50 C019 C46 118.81(19) . . ?
C019 C46 H46 119.7 . . ?
C47 C46 C019 120.5(2) . . ?
C47 C46 H46 119.7 . . ?
C46 C47 C48 121.23(19) . . ?
C46 C47 C51 119.7(2) . . ?
C48 C47 C51 119.0(2) . . ?
C47 C48 H48 121.2 . . ?
C49 C48 C47 117.7(2) . . ?
C49 C48 H48 121.2 . . ?
C48 C49 C50 122.2(2) . . ?
C48 C49 C52 120.2(2) . . ?
C50 C49 C52 117.6(2) . . ?
C019 C50 H50 120.2 . . ?
C49 C50 C019 119.5(2) . . ?
C49 C50 H50 120.2 . . ?
F13 C51 F14 106.5(2) . . ?
F13 C51 F15 106.18(19) . . ?
F13 C51 C47 112.4(2) . . ?
F14 C51 C47 112.53(19) . . ?
F15 C51 F14 105.66(19) . . ?
F15 C51 C47 113.03(19) . . ?
F16 C52 F17 106.6(2) . . ?
F16 C52 F18 105.6(2) . . ?
F16 C52 C49 112.9(2) . . ?
F17 C52 C49 112.1(2) . . ?
F18 C52 F17 106.3(2) . . ?
F18 C52 C49 112.71(19) . . ?
O5 C53 N9 123.6(2) . . ?
O5 C53 N10 122.6(2) . . ?
O5 C53 N10A 115.6(4) . . ?
N9 C53 N10 113.5(2) . . ?
N9 C53 N10A 113.5(4) . . ?
N10 C54 H54A 109.5 . . ?
N10 C54 H54B 109.5 . . ?
N10 C54 C55 110.6(3) . . ?
H54A C54 H54B 108.1 . . ?
C55 C54 H54A 109.5 . . ?
C55 C54 H54B 109.5 . . ?
N11 C55 C54 111.6(2) . . ?
N11 C55 H55A 109.3 . . ?
N11 C55 H55B 109.3 . . ?
C54 C55 H55A 109.3 . . ?
C54 C55 H55B 109.3 . . ?
H55A C55 H55B 108.0 . . ?
O6 C56 N11 120.6(2) . . ?
O6 C56 N12 123.5(2) . . ?
N12 C56 N11 115.97(19) . . ?
N12 C57 C58 106.57(18) . . ?
N12 C57 C59 108.79(19) . . ?
N12 C57 C60 110.6(2) . . ?
C58 C57 C59 109.5(2) . . ?
C58 C57 C60 109.6(2) . . ?
C60 C57 C59 111.69(19) . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C57 C59 H59A 109.5 . . ?
C57 C59 H59B 109.5 . . ?
C57 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C57 C60 H60A 109.5 . . ?
C57 C60 H60B 109.5 . . ?
C57 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
N11 C61 H61A 108.7 . . ?
N11 C61 H61B 108.7 . . ?
N11 C61 C62 114.2(2) . . ?
H61A C61 H61B 107.6 . . ?
C62 C61 H61A 108.7 . . ?
C62 C61 H61B 108.7 . . ?
C63 C62 C61 123.7(2) . . ?
C63 C62 C67 117.7(2) . . ?
C67 C62 C61 118.6(2) . . ?
C62 C63 H63 119.3 . . ?
C62 C63 C64 121.3(2) . . ?
C64 C63 H63 119.3 . . ?
C63 C64 H64 119.9 . . ?
C65 C64 C63 120.1(2) . . ?
C65 C64 H64 119.9 . . ?
C64 C65 H65 120.3 . . ?
C66 C65 C64 119.4(2) . . ?
C66 C65 H65 120.3 . . ?
C65 C66 H66 119.6 . . ?
C65 C66 C67 120.7(2) . . ?
C67 C66 H66 119.6 . . ?
C62 C67 H67 119.7 . . ?
C66 C67 C62 120.7(2) . . ?
C66 C67 H67 119.7 . . ?
N11 C55A H55C 112.1 . . ?
N11 C55A H55D 112.1 . . ?
N11 C55A C54A 98.3(6) . . ?
H55C C55A H55D 109.7 . . ?
C54A C55A H55C 112.1 . . ?
C54A C55A H55D 112.1 . . ?
C55A C54A H54C 109.5 . . ?
C55A C54A H54D 109.5 . . ?
H54C C54A H54D 108.1 . . ?
N10A C54A C55A 110.9(8) . . ?
N10A C54A H54C 109.5 . . ?
N10A C54A H54D 109.5 . . ?
C53 N10A C54A 123.3(7) . . ?
C53 N10A H10A 118.4 . . ?
C54A N10A H10A 118.4 . . ?
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 C7 1.339(3) . ?
F2 C7 1.326(3) . ?
F3 C7 1.335(3) . ?
F4 C8 1.329(3) . ?
F5 C8 1.346(3) . ?
F6 C8 1.320(3) . ?
O1 C9 1.230(2) . ?
O2 C12 1.247(2) . ?
N1 C6 1.402(3) . ?
N1 C9 1.385(3) . ?
N1 H1 0.89(3) . ?
N2 C9 1.350(3) . ?
N2 C10 1.456(3) . ?
N2 H2 0.86(3) . ?
N3 C11 1.465(3) . ?
N3 C12 1.373(3) . ?
N3 C17 1.457(3) . ?
N4 C12 1.348(3) . ?
N4 C13 1.485(3) . ?
N4 H4 0.79(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.385(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.387(3) . ?
C2 C7 1.504(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C4 C5 1.387(3) . ?
C4 C8 1.492(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(3) . ?
C10 H10B 0.9900 . ?
C10 H10C 0.9900 . ?
C10 C11 1.523(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 C14 1.528(3) . ?
C13 C15 1.526(3) . ?
C13 C16 1.530(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.513(3) . ?
C18 C19 1.385(4) . ?
C18 C23 1.395(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.368(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.373(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.400(4) . ?
C23 H23 0.9500 . ?
F7 C29 1.339(3) . ?
F8 C29 1.338(3) . ?
F9 C29 1.327(3) . ?
F10 C30 1.330(3) . ?
F11 C30 1.334(3) . ?
F12 C30 1.316(3) . ?
O3 C31 1.234(2) . ?
O4 C34 1.243(2) . ?
N5 C01A 1.402(3) . ?
N5 C31 1.371(3) . ?
N5 H5A 0.84(3) . ?
N6 C31 1.354(3) . ?
N6 C32 1.456(3) . ?
N6 H6 0.81(3) . ?
N7 C33 1.462(3) . ?
N7 C34 1.374(3) . ?
N7 C39 1.461(3) . ?
N8 C34 1.358(3) . ?
N8 C35 1.480(2) . ?
N8 H8 0.87(3) . ?
C01A C24 1.394(3) . ?
C01A C28 1.397(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.384(3) . ?
C25 C26 1.386(3) . ?
C25 C29 1.497(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.380(3) . ?
C27 C28 1.393(3) . ?
C27 C30 1.502(3) . ?
C28 H28 0.9500 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.535(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C35 C36 1.525(3) . ?
C35 C37 1.533(3) . ?
C35 C38 1.523(3) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.514(3) . ?
C40 C41 1.397(3) . ?
C40 C45 1.389(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.384(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.388(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.385(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.390(3) . ?
C45 H45 0.9500 . ?
F13 C51 1.327(3) . ?
F14 C51 1.345(3) . ?
F15 C51 1.331(3) . ?
F16 C52 1.333(3) . ?
F17 C52 1.337(3) . ?
F18 C52 1.336(3) . ?
O5 C53 1.231(3) . ?
O6 C56 1.244(3) . ?
N9 C019 1.397(3) . ?
N9 C53 1.367(3) . ?
N9 H9 0.83(2) . ?
N10 H10 0.8800 . ?
N10 C53 1.371(3) . ?
N10 C54 1.451(3) . ?
N11 C55 1.504(3) . ?
N11 C56 1.373(3) . ?
N11 C61 1.458(3) . ?
N11 C55A 1.477(8) . ?
N12 C56 1.355(3) . ?
N12 C57 1.475(3) . ?
N12 H12 0.90(3) . ?
C019 C46 1.398(3) . ?
C019 C50 1.393(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.385(3) . ?
C47 C48 1.390(3) . ?
C47 C51 1.498(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.385(3) . ?
C49 C50 1.392(3) . ?
C49 C52 1.496(3) . ?
C50 H50 0.9500 . ?
C53 N10A 1.393(7) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C54 C55 1.525(4) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C57 C58 1.522(3) . ?
C57 C59 1.532(3) . ?
C57 C60 1.531(3) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C61 C62 1.510(3) . ?
C62 C63 1.382(3) . ?
C62 C67 1.402(3) . ?
C63 H63 0.9500 . ?
C63 C64 1.384(3) . ?
C64 H64 0.9500 . ?
C64 C65 1.379(4) . ?
C65 H65 0.9500 . ?
C65 C66 1.373(4) . ?
C66 H66 0.9500 . ?
C66 C67 1.378(3) . ?
C67 H67 0.9500 . ?
C55A H55C 0.9900 . ?
C55A H55D 0.9900 . ?
C55A C54A 1.527(9) . ?
C54A H54C 0.9900 . ?
C54A H54D 0.9900 . ?
C54A N10A 1.454(8) . ?
N10A H10A 0.8800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15A O2 0.98 2.45 3.057(3) 120.0 . yes
C38 H38A O4 0.98 2.47 3.083(3) 120.4 . yes
N10 H10 O2 0.88 2.12 2.927(3) 152.1 3_666 yes
C50 H50 O5 0.95 2.15 2.780(3) 122.6 . yes
C59 H59A O6 0.98 2.47 3.082(3) 120.3 . yes
C60 H60C O6 0.98 2.46 3.071(3) 120.3 . yes
N10A H10A O2 0.88 2.43 3.159(8) 140.1 3_666 yes
N2 H2 O4 0.86(3) 2.17(3) 2.959(2) 152(2) . yes
N1 H1 O4 0.89(3) 2.11(3) 2.952(2) 158(2) . yes
N9 H9 O2 0.83(2) 2.20(2) 2.984(2) 157(2) 3_666 yes
N12 H12 O5 0.90(3) 2.15(3) 3.044(2) 172(3) . yes
N4 H4 O1 0.79(3) 2.30(3) 3.093(2) 174(3) . yes
N5 H5A O6 0.84(3) 2.08(3) 2.900(2) 165(3) . yes
N8 H8 O3 0.87(3) 2.21(3) 3.064(2) 167(2) . yes
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
N2 C10 C11 N3 -161.18(17) . . . . ?
N3 C17 C18 C19 -22.8(3) . . . . ?
N3 C17 C18 C23 157.58(19) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C1 C2 C7 F1 134.8(2) . . . . ?
C1 C2 C7 F2 13.9(4) . . . . ?
C1 C2 C7 F3 -106.6(3) . . . . ?
C2 C1 C6 N1 -179.9(2) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C8 174.9(2) . . . . ?
C3 C2 C7 F1 -47.4(3) . . . . ?
C3 C2 C7 F2 -168.3(2) . . . . ?
C3 C2 C7 F3 71.2(3) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C3 C4 C8 F4 32.6(3) . . . . ?
C3 C4 C8 F5 -86.7(3) . . . . ?
C3 C4 C8 F6 154.8(2) . . . . ?
C4 C5 C6 N1 178.8(2) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C5 C4 C8 F4 -152.1(2) . . . . ?
C5 C4 C8 F5 88.6(3) . . . . ?
C5 C4 C8 F6 -29.9(3) . . . . ?
C6 N1 C9 O1 7.1(4) . . . . ?
C6 N1 C9 N2 -172.6(2) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C6 C1 C2 C7 178.5(2) . . . . ?
C7 C2 C3 C4 -178.7(2) . . . . ?
C8 C4 C5 C6 -173.7(2) . . . . ?
C9 N1 C6 C1 157.5(2) . . . . ?
C9 N1 C6 C5 -22.9(3) . . . . ?
C9 N2 C10 C11 75.7(2) . . . . ?
C10 N2 C9 O1 -5.0(3) . . . . ?
C10 N2 C9 N1 174.78(19) . . . . ?
C11 N3 C12 O2 161.0(2) . . . . ?
C11 N3 C12 N4 -19.6(3) . . . . ?
C11 N3 C17 C18 -79.5(2) . . . . ?
C12 N3 C11 C10 99.5(2) . . . . ?
C12 N3 C17 C18 86.8(2) . . . . ?
C12 N4 C13 C14 -176.2(2) . . . . ?
C12 N4 C13 C15 65.0(3) . . . . ?
C12 N4 C13 C16 -58.3(3) . . . . ?
C13 N4 C12 O2 -15.5(4) . . . . ?
C13 N4 C12 N3 165.1(2) . . . . ?
C17 N3 C11 C10 -94.8(2) . . . . ?
C17 N3 C12 O2 -4.3(3) . . . . ?
C17 N3 C12 N4 175.1(2) . . . . ?
C17 C18 C19 C20 -178.6(2) . . . . ?
C17 C18 C23 C22 -179.9(2) . . . . ?
C18 C19 C20 C21 -1.3(4) . . . . ?
C19 C18 C23 C22 0.4(3) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C20 C21 C22 C23 1.5(4) . . . . ?
C21 C22 C23 C18 -1.7(4) . . . . ?
C23 C18 C19 C20 1.0(4) . . . . ?
N5 C01A C24 C25 178.5(2) . . . . ?
N5 C01A C28 C27 -179.2(2) . . . . ?
N6 C32 C33 N7 163.51(17) . . . . ?
N7 C39 C40 C41 158.45(18) . . . . ?
N7 C39 C40 C45 -22.2(3) . . . . ?
C01A N5 C31 O3 4.0(4) . . . . ?
C01A N5 C31 N6 -175.4(2) . . . . ?
C01A C24 C25 C26 1.0(3) . . . . ?
C01A C24 C25 C29 -176.3(2) . . . . ?
C24 C01A C28 C27 -0.7(3) . . . . ?
C24 C25 C26 C27 -1.2(3) . . . . ?
C24 C25 C29 F7 96.5(3) . . . . ?
C24 C25 C29 F8 -22.2(3) . . . . ?
C24 C25 C29 F9 -143.0(2) . . . . ?
C25 C26 C27 C28 0.4(3) . . . . ?
C25 C26 C27 C30 -177.1(2) . . . . ?
C26 C25 C29 F7 -80.8(3) . . . . ?
C26 C25 C29 F8 160.5(2) . . . . ?
C26 C25 C29 F9 39.7(3) . . . . ?
C26 C27 C28 C01A 0.5(3) . . . . ?
C26 C27 C30 F10 98.4(3) . . . . ?
C26 C27 C30 F11 -20.0(3) . . . . ?
C26 C27 C30 F12 -141.3(2) . . . . ?
C28 C01A C24 C25 -0.1(3) . . . . ?
C28 C27 C30 F10 -79.2(3) . . . . ?
C28 C27 C30 F11 162.4(2) . . . . ?
C28 C27 C30 F12 41.1(3) . . . . ?
C29 C25 C26 C27 176.1(2) . . . . ?
C30 C27 C28 C01A 178.1(2) . . . . ?
C31 N5 C01A C24 143.4(2) . . . . ?
C31 N5 C01A C28 -38.1(3) . . . . ?
C31 N6 C32 C33 -70.2(3) . . . . ?
C32 N6 C31 O3 1.9(3) . . . . ?
C32 N6 C31 N5 -178.7(2) . . . . ?
C33 N7 C34 O4 175.77(19) . . . . ?
C33 N7 C34 N8 -4.2(3) . . . . ?
C33 N7 C39 C40 -84.4(2) . . . . ?
C34 N7 C33 C32 -74.9(2) . . . . ?
C34 N7 C39 C40 97.8(2) . . . . ?
C34 N8 C35 C36 -62.8(3) . . . . ?
C34 N8 C35 C37 179.40(19) . . . . ?
C34 N8 C35 C38 62.1(3) . . . . ?
C35 N8 C34 O4 1.2(3) . . . . ?
C35 N8 C34 N7 -178.79(19) . . . . ?
C39 N7 C33 C32 107.4(2) . . . . ?
C39 N7 C34 O4 -6.5(3) . . . . ?
C39 N7 C34 N8 173.51(18) . . . . ?
C39 C40 C41 C42 -179.55(18) . . . . ?
C39 C40 C45 C44 179.44(19) . . . . ?
C40 C41 C42 C43 0.0(3) . . . . ?
C41 C40 C45 C44 -1.3(3) . . . . ?
C41 C42 C43 C44 -1.1(3) . . . . ?
C42 C43 C44 C45 0.9(3) . . . . ?
C43 C44 C45 C40 0.2(3) . . . . ?
C45 C40 C41 C42 1.1(3) . . . . ?
O5 C53 N10A C54A 7.2(12) . . . . ?
N9 C019 C46 C47 -179.4(2) . . . . ?
N9 C019 C50 C49 178.5(2) . . . . ?
N9 C53 N10A C54A 158.6(8) . . . . ?
N10 C54 C55 N11 159.1(2) . . . . ?
N11 C61 C62 C63 23.9(3) . . . . ?
N11 C61 C62 C67 -156.7(2) . . . . ?
N11 C55A C54A N10A -163.8(7) . . . . ?
C019 N9 C53 O5 7.6(4) . . . . ?
C019 N9 C53 N10 -178.1(2) . . . . ?
C019 N9 C53 N10A -141.2(5) . . . . ?
C019 C46 C47 C48 1.0(3) . . . . ?
C019 C46 C47 C51 -176.4(2) . . . . ?
C46 C019 C50 C49 -1.5(3) . . . . ?
C46 C47 C48 C49 -1.6(3) . . . . ?
C46 C47 C51 F13 87.9(3) . . . . ?
C46 C47 C51 F14 -32.4(3) . . . . ?
C46 C47 C51 F15 -151.9(2) . . . . ?
C47 C48 C49 C50 0.7(3) . . . . ?
C47 C48 C49 C52 179.4(2) . . . . ?
C48 C47 C51 F13 -89.6(3) . . . . ?
C48 C47 C51 F14 150.2(2) . . . . ?
C48 C47 C51 F15 30.6(3) . . . . ?
C48 C49 C50 C019 0.8(4) . . . . ?
C48 C49 C52 F16 25.8(3) . . . . ?
C48 C49 C52 F17 -94.7(3) . . . . ?
C48 C49 C52 F18 145.4(2) . . . . ?
C50 C019 C46 C47 0.6(3) . . . . ?
C50 C49 C52 F16 -155.5(2) . . . . ?
C50 C49 C52 F17 84.1(3) . . . . ?
C50 C49 C52 F18 -35.9(3) . . . . ?
C51 C47 C48 C49 175.8(2) . . . . ?
C52 C49 C50 C019 -177.9(2) . . . . ?
C53 N9 C019 C46 170.4(2) . . . . ?
C53 N9 C019 C50 -9.6(4) . . . . ?
C53 N10 C54 C55 -72.3(4) . . . . ?
C54 N10 C53 O5 0.0(5) . . . . ?
C54 N10 C53 N9 -174.4(3) . . . . ?
C55 N11 C56 O6 -150.4(2) . . . . ?
C55 N11 C56 N12 29.6(3) . . . . ?
C55 N11 C61 C62 67.2(3) . . . . ?
C56 N11 C55 C54 -106.5(3) . . . . ?
C56 N11 C61 C62 -90.1(3) . . . . ?
C56 N11 C55A C54A 96.3(7) . . . . ?
C56 N12 C57 C58 173.4(2) . . . . ?
C56 N12 C57 C59 55.5(3) . . . . ?
C56 N12 C57 C60 -67.5(3) . . . . ?
C57 N12 C56 O6 16.2(4) . . . . ?
C57 N12 C56 N11 -163.8(2) . . . . ?
C61 N11 C55 C54 96.9(3) . . . . ?
C61 N11 C56 O6 6.0(4) . . . . ?
C61 N11 C56 N12 -174.0(2) . . . . ?
C61 N11 C55A C54A -107.9(6) . . . . ?
C61 C62 C63 C64 179.6(2) . . . . ?
C61 C62 C67 C66 -179.4(2) . . . . ?
C62 C63 C64 C65 0.0(3) . . . . ?
C63 C62 C67 C66 0.1(3) . . . . ?
C63 C64 C65 C66 -0.5(4) . . . . ?
C64 C65 C66 C67 0.7(4) . . . . ?
C65 C66 C67 C62 -0.5(4) . . . . ?
C67 C62 C63 C64 0.2(3) . . . . ?
C55A N11 C56 O6 161.3(5) . . . . ?
C55A N11 C56 N12 -18.7(6) . . . . ?
C55A N11 C61 C62 112.9(5) . . . . ?
C55A C54A N10A C53 65.7(13) . . . . ?
