#------------------------------------------------------------------------------
#$Date: 2022-10-26 01:18:14 +0300 (Wed, 26 Oct 2022) $
#$Revision: 278782 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/78/1567842.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_1567842
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         'C31 H42 F6 N6 O3'
_chemical_formula_sum            'C31 H42 F6 N6 O3'
_chemical_formula_weight         660.70
_chemical_melting_point          441
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-31
_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                101.789(2)
_cell_angle_beta                 111.249(2)
_cell_angle_gamma                97.465(2)
_cell_formula_units_Z            4
_cell_length_a                   14.5044(5)
_cell_length_b                   14.9547(5)
_cell_length_c                   17.2099(6)
_cell_measurement_reflns_used    7484
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.74
_cell_measurement_theta_min      2.33
_cell_volume                     3319.6(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_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 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0572
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48350
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.427
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0648 before and 0.0506 after correction. The Ratio of minimum to maximum transmission is 0.8302. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.396
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     949
_refine_ls_number_reflns         12166
_refine_ls_number_restraints     328
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0528
_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)+(0.0724P)²+1.7692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7559
_reflns_number_total             12166
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04716k2.cif
_cod_data_source_block           testt1
_cod_database_code               1567842
_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 C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C4 \\sim N2A-C4 \\sim N2A-C5 \\sim N2-C5
 with sigma of 0.01
 N2A-C12A \\sim N2-C12 \\sim N3-C13 \\sim N3A-C13A \\sim N3-C21 \\sim N3A-C21A
\\sim N5-C22 \\sim N5-C22A
 with sigma of 0.01
 C13A-C12A \\sim C13-C12 \\sim C22-C21 \\sim C22A-C21A
 with sigma of 0.01
 N3-C14 \\sim N3A-C14
 with sigma of 0.01
 N8A-C36 \\sim N8-C36 \\sim N8A-C35 \\sim N8-C35 \\sim N9-C45 \\sim N9A-C45
\\sim N9-C52 \\sim N9A-C52
 with sigma of 0.01
 N8A-C43A \\sim N8-C43 \\sim N9-C44 \\sim N9A-C44A
 with sigma of 0.01
 C44-C43 \\sim C44A-C43A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N2 \\sim N2A \\sim C12 \\sim C12A \\sim C13 \\sim C13A \\sim N3 \\sim C21 \\sim
N3A \\sim C22 \\sim C21A \\sim C22A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
N8 \\sim N9 \\sim C43 \\sim C44 \\sim C43A \\sim C44A \\sim N8A \\sim N9A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N8A) = Uanis(N8)
4. Others
 Sof(H5B)=Sof(H5BC)=Sof(H5BD)=Sof(N2A)=Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=
 Sof(H13C)=Sof(H13D)=Sof(N3A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22C)=
 Sof(H22D)=1-FVAR(1)
 Sof(N2)=Sof(N3)=Sof(H5A)=Sof(H5AA)=Sof(H5AB)=Sof(C12)=Sof(H12A)=Sof(H12B)=
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=FVAR(1)
 Sof(H36C)=Sof(H36D)=Sof(H52C)=Sof(H52D)=Sof(C43A)=Sof(H43C)=Sof(H43D)=
 Sof(C44A)=Sof(H44C)=Sof(H44D)=Sof(N8A)=Sof(N9A)=1-FVAR(2)
 Sof(N8)=Sof(N9)=Sof(H36A)=Sof(H36B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(C44)=
 Sof(H44A)=Sof(H44B)=Sof(H52A)=Sof(H52B)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C1(H1A), C32(H32)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5AA,H5AB), C5(H5BC,H5BD), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B),
  C22(H22A,H22B), C36(H36A,H36B), C36(H36C,H36D), C43(H43A,H43B), C44(H44A,
 H44B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B),
 C50(H50A,H50B), C52(H52A,H52B), C52(H52C,H52D), C53(H53A,H53B), C12A(H12C,
 H12D), C13A(H13C,H13D), C21A(H21C,H21D), C22A(H22C,H22D), C43A(H43C,H43D),
 C44A(H44C,H44D)
5.c Aromatic/amide H refined with riding coordinates:
 N5(H5A), N5(H5B), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C25(H25),
 C27(H27), C29(H29), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C56(H56),
  C58(H58), C60(H60)
5.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C20(H20A,H20B,H20C), C33(H33A,H33B,H33C),
 C34(H34A,H34B,H34C), C51(H51A,H51B,H51C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.41109(16) 0.21104(14) 0.72540(13) 0.0734(6) Uani 1 1 d . . . . .
F2 F 0.39856(16) 0.12662(16) 0.60659(14) 0.0686(6) Uani 1 1 d . . . . .
F3 F 0.31533(15) 0.07440(15) 0.67301(16) 0.0756(7) Uani 1 1 d . . . . .
F4 F -0.08454(13) 0.20740(12) 0.51352(14) 0.0576(5) Uani 1 1 d . . . . .
F5 F -0.03720(14) 0.09843(13) 0.57241(13) 0.0577(5) Uani 1 1 d . . . . .
F6 F -0.06319(13) 0.08457(12) 0.43938(13) 0.0560(5) Uani 1 1 d . . . . .
O1 O -0.05418(13) 0.84904(12) 0.09049(12) 0.0332(4) Uani 1 1 d . . . . .
O2 O -0.10835(14) 0.60928(15) 0.24404(13) 0.0453(5) Uani 1 1 d . . . . .
O3 O 0.08581(14) 0.42918(13) 0.44870(12) 0.0374(5) Uani 1 1 d . . . . .
N1 N -0.11683(18) 0.73713(17) 0.14095(17) 0.0375(6) Uani 1 1 d . . . . .
N2 N 0.0547(3) 0.7704(3) 0.1652(3) 0.0284(13) Uani 0.680(5) 1 d D U P A 1
N3 N 0.0617(3) 0.6203(3) 0.3143(3) 0.0347(11) Uani 0.680(5) 1 d D U P A 1
N4 N -0.06014(17) 0.50233(16) 0.31791(15) 0.0313(5) Uani 1 1 d . . . . .
N5 N 0.23153(17) 0.53658(15) 0.48742(16) 0.0420(6) Uani 1 1 d D . . . .
H5A H 0.298272 0.549041 0.508569 0.050 Uiso 0.680(5) 1 calc R . P A 1
H5B H 0.295295 0.558941 0.523899 0.050 Uiso 0.320(5) 1 calc R . P A 2
N6 N 0.23908(19) 0.40160(15) 0.52936(15) 0.0299(5) Uani 1 1 d . . . . .
C1 C -0.22262(19) 0.73901(19) 0.09504(18) 0.0333(6) Uani 1 1 d . . . . .
H1A H -0.225379 0.802929 0.086507 0.040 Uiso 1 1 calc R . . . .
C2 C -0.2817(2) 0.7211(3) 0.1489(2) 0.0540(9) Uani 1 1 d . . . . .
H2A H -0.280716 0.658284 0.157204 0.081 Uiso 1 1 calc GR . . . .
H2B H -0.351981 0.725579 0.119030 0.081 Uiso 1 1 calc GR . . . .
H2C H -0.250630 0.767882 0.205405 0.081 Uiso 1 1 calc GR . . . .
C3 C -0.2671(2) 0.6683(2) 0.0065(2) 0.0451(8) Uani 1 1 d . . . . .
H3A H -0.229235 0.684371 -0.027620 0.068 Uiso 1 1 calc GR . . . .
H3B H -0.338478 0.669530 -0.023515 0.068 Uiso 1 1 calc GR . . . .
H3C H -0.262214 0.605460 0.013471 0.068 Uiso 1 1 calc GR . . . .
C4 C -0.04073(19) 0.78986(19) 0.13259(18) 0.0337(7) Uani 1 1 d D . . . .
C5 C 0.1412(2) 0.83787(19) 0.17163(19) 0.0361(7) Uani 1 1 d D . . . .
H5AA H 0.118401 0.861320 0.119526 0.043 Uiso 0.680(5) 1 calc R . P A 1
H5AB H 0.193366 0.802751 0.167657 0.043 Uiso 0.680(5) 1 calc R . P A 1
H5BC H 0.114191 0.856313 0.117014 0.043 Uiso 0.320(5) 1 calc R . P A 2
H5BD H 0.187341 0.795584 0.167459 0.043 Uiso 0.320(5) 1 calc R . P A 2
C6 C 0.1937(2) 0.9228(2) 0.24941(18) 0.0333(7) Uani 1 1 d . . . . .
C7 C 0.1439(2) 0.9617(2) 0.29776(19) 0.0420(8) Uani 1 1 d . . . . .
H7 H 0.074707 0.934670 0.282821 0.050 Uiso 1 1 calc R . . . .
C8 C 0.1940(3) 1.0402(3) 0.3682(2) 0.0512(9) Uani 1 1 d . . . . .
H8 H 0.158772 1.066598 0.400849 0.061 Uiso 1 1 calc R . . . .
C9 C 0.2946(3) 1.0800(2) 0.3908(2) 0.0493(8) Uani 1 1 d . . . . .
H9 H 0.328792 1.133398 0.439171 0.059 Uiso 1 1 calc R . . . .
C10 C 0.3452(2) 1.0420(2) 0.3432(2) 0.0452(8) Uani 1 1 d . . . . .
H10 H 0.414500 1.069134 0.358524 0.054 Uiso 1 1 calc R . . . .
C11 C 0.2951(2) 0.9640(2) 0.27276(19) 0.0383(7) Uani 1 1 d . . . . .
H11 H 0.330497 0.938282 0.239936 0.046 Uiso 1 1 calc R . . . .
C12 C 0.0726(3) 0.6908(3) 0.2004(2) 0.0299(10) Uani 0.680(5) 1 d D U P A 1
H12A H 0.135340 0.674457 0.197120 0.036 Uiso 0.680(5) 1 calc R . P A 1
H12B H 0.015682 0.636354 0.164007 0.036 Uiso 0.680(5) 1 calc R . P A 1
C13 C 0.0832(3) 0.7081(3) 0.2937(3) 0.0339(11) Uani 0.680(5) 1 d D U P A 1
H13A H 0.153042 0.743191 0.333072 0.041 Uiso 0.680(5) 1 calc R . P A 1
H13B H 0.035634 0.746852 0.302699 0.041 Uiso 0.680(5) 1 calc R . P A 1
C14 C -0.0405(2) 0.5752(2) 0.28748(19) 0.0415(8) Uani 1 1 d D . . . .
C15 C -0.1634(2) 0.46556(19) 0.30706(19) 0.0350(7) Uani 1 1 d . . . . .
H15A H -0.211028 0.459595 0.247078 0.042 Uiso 1 1 calc R . . . .
H15B H -0.182133 0.509602 0.347143 0.042 Uiso 1 1 calc R . . . .
C16 C -0.1721(2) 0.37032(19) 0.32544(18) 0.0351(7) Uani 1 1 d . . . . .
H16A H -0.116709 0.374800 0.381569 0.042 Uiso 1 1 calc R . . . .
H16B H -0.237306 0.353384 0.330944 0.042 Uiso 1 1 calc R . . . .
C17 C -0.1668(2) 0.29335(19) 0.25611(19) 0.0385(7) Uani 1 1 d . . . . .
H17A H -0.104144 0.312782 0.247418 0.046 Uiso 1 1 calc R . . . .
H17B H -0.225255 0.285814 0.200992 0.046 Uiso 1 1 calc R . . . .
C18 C -0.1673(2) 0.1992(2) 0.2765(2) 0.0435(8) Uani 1 1 d . . . . .
H18A H -0.099257 0.201036 0.319652 0.052 Uiso 1 1 calc R . . . .
H18B H -0.216422 0.189207 0.303306 0.052 Uiso 1 1 calc R . . . .
C19 C -0.1945(3) 0.1170(2) 0.1988(2) 0.0549(9) Uani 1 1 d . . . . .
H19A H -0.149962 0.130068 0.168541 0.066 Uiso 1 1 calc R . . . .
H19B H -0.265245 0.111318 0.158386 0.066 Uiso 1 1 calc R . . . .
C20 C -0.1852(4) 0.0243(2) 0.2194(3) 0.0826(14) Uani 1 1 d . . . . .
H20A H -0.207632 -0.025562 0.165458 0.124 Uiso 1 1 calc GR . . . .
H20B H -0.227745 0.011158 0.250692 0.124 Uiso 1 1 calc GR . . . .
H20C H -0.114306 0.027253 0.255563 0.124 Uiso 1 1 calc GR . . . .
C21 C 0.1437(4) 0.5770(4) 0.3563(4) 0.0334(13) Uani 0.680(5) 1 d D U P A 1
H21A H 0.202377 0.596532 0.342335 0.040 Uiso 0.680(5) 1 calc R . P A 1
H21B H 0.120725 0.507941 0.333867 0.040 Uiso 0.680(5) 1 calc R . P A 1
C22 C 0.1761(6) 0.6048(4) 0.4534(4) 0.0331(15) Uani 0.680(5) 1 d D U P A 1
H22A H 0.220210 0.668667 0.479083 0.040 Uiso 0.680(5) 1 calc R . P A 1
H22B H 0.115872 0.604505 0.467826 0.040 Uiso 0.680(5) 1 calc R . P A 1
C23 C 0.1788(2) 0.45404(18) 0.48589(17) 0.0325(6) Uani 1 1 d . . . . .
C24 C 0.2074(2) 0.31705(17) 0.54469(16) 0.0274(6) Uani 1 1 d . . . . .
C25 C 0.2826(2) 0.27332(18) 0.58542(16) 0.0292(6) Uani 1 1 d . . . . .
H25 H 0.351570 0.300540 0.599628 0.035 Uiso 1 1 calc R . . . .
C26 C 0.2589(2) 0.19047(18) 0.60577(17) 0.0297(6) Uani 1 1 d . . . . .
C27 C 0.1590(2) 0.14948(18) 0.58538(17) 0.0307(6) Uani 1 1 d . . . . .
H27 H 0.142298 0.093288 0.599813 0.037 Uiso 1 1 calc R . . . .
C28 C 0.0839(2) 0.19214(17) 0.54350(16) 0.0284(6) Uani 1 1 d . . . . .
C29 C 0.1063(2) 0.27529(18) 0.52293(17) 0.0300(6) Uani 1 1 d . . . . .
H29 H 0.053344 0.303362 0.494369 0.036 Uiso 1 1 calc R . . . .
C30 C 0.3440(2) 0.14987(19) 0.65169(19) 0.0354(7) Uani 1 1 d . . . . .
C31 C -0.0239(2) 0.1471(2) 0.5181(2) 0.0407(7) Uani 1 1 d . . . . .
F7 F 1.45749(14) 1.28506(12) 1.18967(12) 0.0546(5) Uani 1 1 d . . . . .
F8 F 1.49537(15) 1.26114(13) 1.08049(13) 0.0599(5) Uani 1 1 d . . . . .
F9 F 1.58555(13) 1.22694(14) 1.19509(14) 0.0707(6) Uani 1 1 d . . . . .
F10 F 1.54262(16) 0.89244(15) 1.11773(17) 0.0841(7) Uani 1 1 d . . . . .
F11 F 1.40408(17) 0.80947(14) 1.01774(15) 0.0730(6) Uani 1 1 d . . . . .
F12 F 1.41876(18) 0.83728(15) 1.14765(14) 0.0734(6) Uani 1 1 d . . . . .
O4 O 0.43214(14) 0.51606(13) 0.57839(13) 0.0410(5) Uani 1 1 d . . . . .
O5 O 0.78956(15) 0.58110(14) 0.78670(15) 0.0508(6) Uani 1 1 d . . . . .
O6 O 1.08538(13) 0.86682(12) 0.96360(12) 0.0317(4) Uani 1 1 d . . . . .
N7 N 0.5777(2) 0.52681(18) 0.69298(17) 0.0419(7) Uani 1 1 d . . . . .
N8 N 0.5634(2) 0.64197(19) 0.61896(18) 0.0347(9) Uani 0.849(5) 1 d D U P B 1
N9 N 0.8431(2) 0.7115(2) 0.75193(19) 0.0325(9) Uani 0.849(5) 1 d D U P B 1
N10 N 0.93993(18) 0.67590(18) 0.87780(17) 0.0375(6) Uani 1 1 d . . . . .
N11 N 0.98907(16) 0.95471(16) 0.89076(15) 0.0309(5) Uani 1 1 d . . . . .
N12 N 1.15340(16) 1.02205(16) 0.98354(14) 0.0298(5) Uani 1 1 d . . . . .
C32 C 0.5348(2) 0.4466(2) 0.7158(2) 0.0392(7) Uani 1 1 d . . . . .
H32 H 0.491759 0.396938 0.660855 0.047 Uiso 1 1 calc R . . . .
C33 C 0.6205(2) 0.4078(2) 0.7683(2) 0.0540(9) Uani 1 1 d . . . . .
H33A H 0.659594 0.388528 0.734248 0.081 Uiso 1 1 calc GR . . . .
H33B H 0.592547 0.353485 0.782958 0.081 Uiso 1 1 calc GR . . . .
H33C H 0.665058 0.456130 0.821622 0.081 Uiso 1 1 calc GR . . . .
C34 C 0.4679(3) 0.4737(2) 0.7628(2) 0.0505(8) Uani 1 1 d . . . . .
H34A H 0.509365 0.519611 0.818590 0.076 Uiso 1 1 calc GR . . . .
H34B H 0.435501 0.417814 0.772575 0.076 Uiso 1 1 calc GR . . . .
H34C H 0.415589 0.501124 0.727574 0.076 Uiso 1 1 calc GR . . . .
C35 C 0.5210(2) 0.55722(19) 0.62783(19) 0.0379(7) Uani 1 1 d D . . . .
C36 C 0.5176(2) 0.6618(2) 0.53543(19) 0.0432(8) Uani 1 1 d D . . . .
H36A H 0.473233 0.603142 0.491864 0.052 Uiso 0.849(5) 1 calc R . P B 1
H36B H 0.572058 0.682784 0.517034 0.052 Uiso 0.849(5) 1 calc R . P B 1
H36C H 0.470416 0.608897 0.485981 0.052 Uiso 0.151(5) 1 calc R . P B 2
H36D H 0.568853 0.687693 0.515691 0.052 Uiso 0.151(5) 1 calc R . P B 2
C37 C 0.4559(2) 0.7355(2) 0.53674(19) 0.0368(7) Uani 1 1 d . . . . .
C38 C 0.4234(2) 0.7627(2) 0.6020(2) 0.0448(8) Uani 1 1 d . . . . .
H38 H 0.439789 0.734589 0.648565 0.054 Uiso 1 1 calc R . . . .
C39 C 0.3665(2) 0.8312(2) 0.6002(3) 0.0566(9) Uani 1 1 d . . . . .
H39 H 0.345327 0.850228 0.645951 0.068 Uiso 1 1 calc R . . . .
C40 C 0.3410(3) 0.8710(2) 0.5323(3) 0.0589(10) Uani 1 1 d . . . . .
H40 H 0.301975 0.917468 0.531117 0.071 Uiso 1 1 calc R . . . .
C41 C 0.3715(3) 0.8440(2) 0.4666(2) 0.0538(9) Uani 1 1 d . . . . .
H41 H 0.353143 0.871152 0.419419 0.065 Uiso 1 1 calc R . . . .
C42 C 0.4294(2) 0.7769(2) 0.4687(2) 0.0443(8) Uani 1 1 d . . . . .
H42 H 0.451131 0.758987 0.423106 0.053 Uiso 1 1 calc R . . . .
C43 C 0.6589(2) 0.7036(2) 0.6855(2) 0.0324(8) Uani 0.849(5) 1 d D U P B 1
H43A H 0.664839 0.696531 0.742940 0.039 Uiso 0.849(5) 1 calc R . P B 1
H43B H 0.656066 0.769499 0.685865 0.039 Uiso 0.849(5) 1 calc R . P B 1
C44 C 0.7535(2) 0.6837(2) 0.6719(2) 0.0346(9) Uani 0.849(5) 1 d D U P B 1
H44A H 0.741987 0.615813 0.645116 0.042 Uiso 0.849(5) 1 calc R . P B 1
H44B H 0.764747 0.717688 0.631300 0.042 Uiso 0.849(5) 1 calc R . P B 1
C45 C 0.8545(2) 0.65448(19) 0.80715(19) 0.0388(7) Uani 1 1 d D . . . .
C46 C 0.9583(2) 0.6132(2) 0.9342(2) 0.0431(8) Uani 1 1 d . . . . .
H46A H 0.928656 0.547566 0.898366 0.052 Uiso 1 1 calc R . . . .
H46B H 0.923892 0.626793 0.974113 0.052 Uiso 1 1 calc R . . . .
C47 C 1.0691(2) 0.6241(2) 0.9859(2) 0.0436(8) Uani 1 1 d . . . . .
H47A H 1.096482 0.689560 1.022728 0.052 Uiso 1 1 calc R . . . .
H47B H 1.076073 0.583098 1.025164 0.052 Uiso 1 1 calc R . . . .
C48 C 1.1343(2) 0.6033(2) 0.9383(2) 0.0422(7) Uani 1 1 d . . . . .
H48A H 1.135893 0.650192 0.905419 0.051 Uiso 1 1 calc R . . . .
H48B H 1.102530 0.541096 0.895655 0.051 Uiso 1 1 calc R . . . .
C49 C 1.2411(2) 0.6030(2) 0.9930(2) 0.0401(7) Uani 1 1 d . . . . .
H49A H 1.271099 0.664058 1.037597 0.048 Uiso 1 1 calc R . . . .
H49B H 1.238969 0.554070 1.023726 0.048 Uiso 1 1 calc R . . . .
C50 C 1.3110(2) 0.5869(2) 0.9489(2) 0.0455(8) Uani 1 1 d . . . . .
H50A H 1.315361 0.637082 0.919921 0.055 Uiso 1 1 calc R . . . .
H50B H 1.280320 0.526781 0.903099 0.055 Uiso 1 1 calc R . . . .
C51 C 1.4160(2) 0.5840(2) 1.0043(2) 0.0496(8) Uani 1 1 d . . . . .
H51A H 1.455120 0.573653 0.968618 0.074 Uiso 1 1 calc GR . . . .
H51B H 1.413595 0.532717 1.031602 0.074 Uiso 1 1 calc GR . . . .
H51C H 1.448480 0.643573 1.049314 0.074 Uiso 1 1 calc GR . . . .
C52 C 0.9119(2) 0.80255(18) 0.77856(18) 0.0365(7) Uani 1 1 d D . . . .
H52A H 0.901138 0.825919 0.726812 0.044 Uiso 0.849(5) 1 calc R . P B 1
H52B H 0.982521 0.794080 0.800914 0.044 Uiso 0.849(5) 1 calc R . P B 1
H52C H 0.898237 0.819542 0.723403 0.044 Uiso 0.151(5) 1 calc R . P B 2
H52D H 0.978349 0.784843 0.798910 0.044 Uiso 0.151(5) 1 calc R . P B 2
C53 C 0.90060(19) 0.87721(19) 0.84757(19) 0.0355(7) Uani 1 1 d . . . . .
H53A H 0.840044 0.901578 0.820146 0.043 Uiso 1 1 calc R . . . .
H53B H 0.889602 0.848189 0.891220 0.043 Uiso 1 1 calc R . . . .
C54 C 1.07602(19) 0.94235(18) 0.94685(17) 0.0273(6) Uani 1 1 d . . . . .
C55 C 1.25586(19) 1.02793(18) 1.03075(16) 0.0279(6) Uani 1 1 d . . . . .
C56 C 1.32066(19) 1.11726(19) 1.06664(17) 0.0302(6) Uani 1 1 d . . . . .
H56 H 1.293154 1.171053 1.061111 0.036 Uiso 1 1 calc R . . . .
C57 C 1.4242(2) 1.12801(19) 1.11003(17) 0.0319(6) Uani 1 1 d . . . . .
C58 C 1.4666(2) 1.0512(2) 1.12001(18) 0.0367(7) Uani 1 1 d . . . . .
H58 H 1.537725 1.058586 1.149606 0.044 Uiso 1 1 calc R . . . .
C59 C 1.4018(2) 0.9627(2) 1.08537(19) 0.0372(7) Uani 1 1 d . . . . .
C60 C 1.2981(2) 0.95080(19) 1.04171(18) 0.0344(7) Uani 1 1 d . . . . .
H60 H 1.255582 0.889630 1.019137 0.041 Uiso 1 1 calc R . . . .
C61 C 1.4903(2) 1.2245(2) 1.1434(2) 0.0409(7) Uani 1 1 d . . . . .
C62 C 1.4447(2) 0.8774(2) 1.0936(2) 0.0527(9) Uani 1 1 d . . . . .
N2A N 0.0593(4) 0.7945(8) 0.1919(6) 0.031(3) Uani 0.320(5) 1 d D U P A 2
C12A C 0.0756(6) 0.7421(5) 0.2574(5) 0.0286(18) Uani 0.320(5) 1 d D U P A 2
H12C H 0.024093 0.748402 0.282081 0.034 Uiso 0.320(5) 1 calc R . P A 2
H12D H 0.143138 0.770950 0.304936 0.034 Uiso 0.320(5) 1 calc R . P A 2
C13A C 0.0701(6) 0.6390(5) 0.2239(5) 0.0302(18) Uani 0.320(5) 1 d D U P A 2
H13C H 0.013959 0.614328 0.165778 0.036 Uiso 0.320(5) 1 calc R . P A 2
H13D H 0.134036 0.631652 0.217497 0.036 Uiso 0.320(5) 1 calc R . P A 2
N3A N 0.0540(5) 0.5835(7) 0.2803(6) 0.0298(19) Uani 0.320(5) 1 d D U P A 2
C21A C 0.1344(9) 0.5428(8) 0.3299(7) 0.033(2) Uani 0.320(5) 1 d D U P A 2
H21C H 0.189291 0.548456 0.308725 0.040 Uiso 0.320(5) 1 calc R . P A 2
H21D H 0.106741 0.475225 0.318897 0.040 Uiso 0.320(5) 1 calc R . P A 2
C22A C 0.1794(13) 0.5877(9) 0.4266(7) 0.036(3) Uani 0.320(5) 1 d D U P A 2
H22C H 0.228249 0.646450 0.437865 0.043 Uiso 0.320(5) 1 calc R . P A 2
H22D H 0.123799 0.605901 0.442087 0.043 Uiso 0.320(5) 1 calc R . P A 2
H4 H -0.011(2) 0.484(2) 0.3564(19) 0.038(8) Uiso 1 1 d . . . . .
H7A H 0.637(2) 0.548(2) 0.7192(19) 0.037(9) Uiso 1 1 d . . . . .
H1 H -0.103(2) 0.707(2) 0.1743(19) 0.040(9) Uiso 1 1 d . . . . .
H10A H 0.976(2) 0.728(2) 0.9001(19) 0.036(9) Uiso 1 1 d . . . . .
H12 H 1.136(2) 1.072(2) 0.9694(18) 0.039(8) Uiso 1 1 d . . . . .
H6 H 0.299(2) 0.422(2) 0.5503(18) 0.032(8) Uiso 1 1 d . . . . .
H11A H 0.987(2) 1.008(2) 0.8843(19) 0.047(9) Uiso 1 1 d . . . . .
C43A C 0.6801(9) 0.6525(12) 0.6345(9) 0.033(3) Uani 0.151(5) 1 d D U P B 2
H43C H 0.699199 0.686367 0.596901 0.039 Uiso 0.151(5) 1 calc R . P B 2
H43D H 0.713487 0.598858 0.636617 0.039 Uiso 0.151(5) 1 calc R . P B 2
C44A C 0.7197(9) 0.7181(12) 0.7255(9) 0.032(3) Uani 0.151(5) 1 d D U P B 2
H44C H 0.703001 0.779477 0.721327 0.039 Uiso 0.151(5) 1 calc R . P B 2
H44D H 0.683998 0.692100 0.758074 0.039 Uiso 0.151(5) 1 calc R . P B 2
N8A N 0.5715(8) 0.6172(13) 0.5964(11) 0.0347(9) Uani 0.151(5) 1 d D U P B 2
N9A N 0.8295(7) 0.7328(9) 0.7745(13) 0.035(4) Uani 0.151(5) 1 d D 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
C1 N1 H1 120(2) . . ?
C4 N1 C1 122.2(2) . . ?
C4 N1 H1 118(2) . . ?
C4 N2 C5 118.0(3) . . ?
C4 N2 C12 122.6(3) . . ?
C12 N2 C5 119.2(3) . . ?
C13 N3 C21 120.8(4) . . ?
C14 N3 C13 118.2(3) . . ?
C14 N3 C21 120.9(3) . . ?
C14 N4 C15 120.0(2) . . ?
C14 N4 H4 122.3(18) . . ?
C15 N4 H4 115.8(18) . . ?
C22 N5 H5A 120.4 . . ?
C23 N5 H5A 120.4 . . ?
C23 N5 H5B 120.9 . . ?
C23 N5 C22 119.2(4) . . ?
C23 N5 C22A 118.2(7) . . ?
C22A N5 H5B 120.9 . . ?
C23 N6 C24 127.2(2) . . ?
C23 N6 H6 118(2) . . ?
C24 N6 H6 115(2) . . ?
N1 C1 H1A 108.3 . . ?
N1 C1 C2 109.8(2) . . ?
N1 C1 C3 110.1(2) . . ?
C2 C1 H1A 108.3 . . ?
C2 C1 C3 111.9(2) . . ?
C3 C1 H1A 108.3 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N1 122.7(2) . . ?
O1 C4 N2 119.2(3) . . ?
O1 C4 N2A 118.6(4) . . ?
N1 C4 N2 117.8(3) . . ?
N1 C4 N2A 116.7(4) . . ?
N2 C5 H5AA 107.1 . . ?
N2 C5 H5AB 107.1 . . ?
N2 C5 C6 120.9(3) . . ?
H5AA C5 H5AB 106.8 . . ?
H5BC C5 H5BD 109.3 . . ?
C6 C5 H5AA 107.1 . . ?
C6 C5 H5AB 107.1 . . ?
C6 C5 H5BC 111.5 . . ?
C6 C5 H5BD 111.5 . . ?
N2A C5 H5BC 111.5 . . ?
N2A C5 H5BD 111.5 . . ?
N2A C5 C6 101.3(5) . . ?
C7 C6 C5 122.1(2) . . ?
C7 C6 C11 118.4(3) . . ?
C11 C6 C5 119.5(3) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C6 C11 H11 119.5 . . ?
C10 C11 C6 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
N2 C12 H12A 108.8 . . ?
N2 C12 H12B 108.8 . . ?
N2 C12 C13 113.9(4) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
N3 C13 C12 111.0(4) . . ?
N3 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O2 C14 N3 119.2(3) . . ?
O2 C14 N4 122.6(3) . . ?
O2 C14 N3A 121.3(4) . . ?
N4 C14 N3 117.9(3) . . ?
N4 C14 N3A 111.8(4) . . ?
N4 C15 H15A 109.6 . . ?
N4 C15 H15B 109.6 . . ?
N4 C15 C16 110.4(2) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.4(2) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C16 C17 C18 114.2(2) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 C17 114.3(3) . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 108.6 . . ?
C18 C19 H19B 108.6 . . ?
C18 C19 C20 114.7(3) . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 C22 110.9(4) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
N5 C22 C21 107.4(4) . . ?
N5 C22 H22A 110.2 . . ?
N5 C22 H22B 110.2 . . ?
C21 C22 H22A 110.2 . . ?
C21 C22 H22B 110.2 . . ?
H22A C22 H22B 108.5 . . ?
O3 C23 N5 122.7(2) . . ?
O3 C23 N6 123.8(2) . . ?
N5 C23 N6 113.5(2) . . ?
C25 C24 N6 117.0(2) . . ?
C25 C24 C29 118.7(2) . . ?
C29 C24 N6 124.4(2) . . ?
C24 C25 H25 119.4 . . ?
C24 C25 C26 121.2(2) . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C30 117.8(2) . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 C30 121.9(2) . . ?
C26 C27 H27 120.8 . . ?
C26 C27 C28 118.5(2) . . ?
C28 C27 H27 120.8 . . ?
C27 C28 C29 122.0(2) . . ?
C27 C28 C31 119.1(2) . . ?
C29 C28 C31 118.9(2) . . ?
C24 C29 H29 120.3 . . ?
C28 C29 C24 119.3(3) . . ?
C28 C29 H29 120.3 . . ?
F1 C30 C26 111.9(2) . . ?
F2 C30 F1 104.3(3) . . ?
F2 C30 C26 113.2(2) . . ?
F3 C30 F1 106.2(2) . . ?
F3 C30 F2 106.6(2) . . ?
F3 C30 C26 113.9(2) . . ?
F4 C31 F5 106.7(2) . . ?
F4 C31 F6 105.8(2) . . ?
F4 C31 C28 113.7(2) . . ?
F5 C31 F6 105.3(2) . . ?
F5 C31 C28 113.0(2) . . ?
F6 C31 C28 111.8(2) . . ?
C32 N7 H7A 117(2) . . ?
C35 N7 C32 121.1(2) . . ?
C35 N7 H7A 122(2) . . ?
C35 N8 C36 117.4(2) . . ?
C35 N8 C43 122.3(2) . . ?
C36 N8 C43 119.8(2) . . ?
C44 N9 C52 120.8(3) . . ?
C45 N9 C44 117.8(2) . . ?
C45 N9 C52 120.9(3) . . ?
C45 N10 C46 119.8(2) . . ?
C45 N10 H10A 124(2) . . ?
C46 N10 H10A 114(2) . . ?
C53 N11 H11A 122(2) . . ?
C54 N11 C53 119.9(2) . . ?
C54 N11 H11A 118(2) . . ?
C54 N12 C55 127.2(2) . . ?
C54 N12 H12 114.9(19) . . ?
C55 N12 H12 117(2) . . ?
N7 C32 H32 108.1 . . ?
N7 C32 C33 108.9(2) . . ?
N7 C32 C34 111.2(3) . . ?
C33 C32 H32 108.1 . . ?
C33 C32 C34 112.4(3) . . ?
C34 C32 H32 108.1 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O4 C35 N7 123.0(2) . . ?
O4 C35 N8 119.7(2) . . ?
O4 C35 N8A 116.1(6) . . ?
N7 C35 N8 117.1(2) . . ?
N7 C35 N8A 117.4(5) . . ?
N8 C36 H36A 108.9 . . ?
N8 C36 H36B 108.9 . . ?
N8 C36 C37 113.6(3) . . ?
H36A C36 H36B 107.7 . . ?
H36C C36 H36D 105.3 . . ?
C37 C36 H36A 108.9 . . ?
C37 C36 H36B 108.9 . . ?
C37 C36 H36C 103.5 . . ?
C37 C36 H36D 103.5 . . ?
N8A C36 H36C 103.5 . . ?
N8A C36 H36D 103.5 . . ?
N8A C36 C37 134.9(9) . . ?
C38 C37 C36 122.8(3) . . ?
C38 C37 C42 118.4(3) . . ?
C42 C37 C36 118.8(3) . . ?
C37 C38 H38 119.7 . . ?
C37 C38 C39 120.6(3) . . ?
C39 C38 H38 119.7 . . ?
C38 C39 H39 120.0 . . ?
C40 C39 C38 120.1(3) . . ?
C40 C39 H39 120.0 . . ?
C39 C40 H40 120.0 . . ?
C41 C40 C39 120.1(3) . . ?
C41 C40 H40 120.0 . . ?
C40 C41 H41 120.0 . . ?
C40 C41 C42 120.1(3) . . ?
C42 C41 H41 120.0 . . ?
C37 C42 H42 119.6 . . ?
C41 C42 C37 120.8(3) . . ?
C41 C42 H42 119.6 . . ?
N8 C43 H43A 108.8 . . ?
N8 C43 H43B 108.8 . . ?
N8 C43 C44 113.8(3) . . ?
H43A C43 H43B 107.7 . . ?
C44 C43 H43A 108.8 . . ?
C44 C43 H43B 108.8 . . ?
N9 C44 C43 112.5(3) . . ?
N9 C44 H44A 109.1 . . ?
N9 C44 H44B 109.1 . . ?
C43 C44 H44A 109.1 . . ?
C43 C44 H44B 109.1 . . ?
H44A C44 H44B 107.8 . . ?
O5 C45 N9 120.1(3) . . ?
O5 C45 N10 121.5(3) . . ?
O5 C45 N9A 121.6(5) . . ?
N10 C45 N9 118.2(2) . . ?
N10 C45 N9A 114.0(7) . . ?
N10 C46 H46A 109.2 . . ?
N10 C46 H46B 109.2 . . ?
N10 C46 C47 111.9(2) . . ?
H46A C46 H46B 107.9 . . ?
C47 C46 H46A 109.2 . . ?
C47 C46 H46B 109.2 . . ?
C46 C47 H47A 107.8 . . ?
C46 C47 H47B 107.8 . . ?
H47A C47 H47B 107.1 . . ?
C48 C47 C46 118.0(3) . . ?
C48 C47 H47A 107.8 . . ?
C48 C47 H47B 107.8 . . ?
C47 C48 H48A 108.4 . . ?
C47 C48 H48B 108.4 . . ?
C47 C48 C49 115.5(3) . . ?
H48A C48 H48B 107.5 . . ?
C49 C48 H48A 108.4 . . ?
C49 C48 H48B 108.4 . . ?
C48 C49 H49A 107.9 . . ?
C48 C49 H49B 107.9 . . ?
H49A C49 H49B 107.2 . . ?
C50 C49 C48 117.7(3) . . ?
C50 C49 H49A 107.9 . . ?
C50 C49 H49B 107.9 . . ?
C49 C50 H50A 108.1 . . ?
C49 C50 H50B 108.1 . . ?
C49 C50 C51 116.7(3) . . ?
H50A C50 H50B 107.3 . . ?
C51 C50 H50A 108.1 . . ?
C51 C50 H50B 108.1 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N9 C52 H52A 108.5 . . ?
N9 C52 H52B 108.5 . . ?
N9 C52 C53 115.2(3) . . ?
H52A C52 H52B 107.5 . . ?
H52C C52 H52D 110.5 . . ?
C53 C52 H52A 108.5 . . ?
C53 C52 H52B 108.5 . . ?
C53 C52 H52C 113.1 . . ?
C53 C52 H52D 113.1 . . ?
N9A C52 H52C 113.1 . . ?
N9A C52 H52D 113.1 . . ?
N9A C52 C53 93.1(9) . . ?
N11 C53 C52 112.4(2) . . ?
N11 C53 H53A 109.1 . . ?
N11 C53 H53B 109.1 . . ?
C52 C53 H53A 109.1 . . ?
C52 C53 H53B 109.1 . . ?
H53A C53 H53B 107.9 . . ?
O6 C54 N11 122.9(2) . . ?
O6 C54 N12 123.5(2) . . ?
N11 C54 N12 113.6(2) . . ?
N12 C55 C56 117.6(2) . . ?
C60 C55 N12 124.1(2) . . ?
C60 C55 C56 118.2(2) . . ?
C55 C56 H56 119.6 . . ?
C57 C56 C55 120.8(3) . . ?
C57 C56 H56 119.6 . . ?
C56 C57 C58 121.1(3) . . ?
C56 C57 C61 118.5(3) . . ?
C58 C57 C61 120.4(3) . . ?
C57 C58 H58 121.0 . . ?
C57 C58 C59 118.0(3) . . ?
C59 C58 H58 121.0 . . ?
C58 C59 C62 119.7(3) . . ?
C60 C59 C58 121.6(3) . . ?
C60 C59 C62 118.6(3) . . ?
C55 C60 H60 119.8 . . ?
C59 C60 C55 120.3(3) . . ?
C59 C60 H60 119.8 . . ?
F7 C61 F9 106.1(2) . . ?
F7 C61 C57 112.6(2) . . ?
F8 C61 F7 105.5(3) . . ?
F8 C61 F9 106.8(2) . . ?
F8 C61 C57 112.9(2) . . ?
F9 C61 C57 112.4(3) . . ?
F10 C62 F11 106.3(3) . . ?
F10 C62 F12 109.3(3) . . ?
F10 C62 C59 114.5(3) . . ?
F11 C62 C59 111.4(3) . . ?
F12 C62 F11 103.6(3) . . ?
F12 C62 C59 111.0(3) . . ?
C4 N2A C5 115.4(5) . . ?
C4 N2A C12A 120.3(5) . . ?
C5 N2A C12A 123.2(6) . . ?
N2A C12A H12C 108.6 . . ?
N2A C12A H12D 108.6 . . ?
N2A C12A C13A 114.6(8) . . ?
H12C C12A H12D 107.6 . . ?
C13A C12A H12C 108.6 . . ?
C13A C12A H12D 108.6 . . ?
C12A C13A H13C 108.9 . . ?
C12A C13A H13D 108.9 . . ?
H13C C13A H13D 107.7 . . ?
N3A C13A C12A 113.3(7) . . ?
N3A C13A H13C 108.9 . . ?
N3A C13A H13D 108.9 . . ?
C14 N3A C13A 116.8(6) . . ?
C14 N3A C21A 122.2(7) . . ?
C13A N3A C21A 121.0(8) . . ?
N3A C21A H21C 108.7 . . ?
N3A C21A H21D 108.7 . . ?
N3A C21A C22A 114.3(9) . . ?
H21C C21A H21D 107.6 . . ?
C22A C21A H21C 108.7 . . ?
C22A C21A H21D 108.7 . . ?
N5 C22A C21A 120.7(9) . . ?
N5 C22A H22C 107.1 . . ?
N5 C22A H22D 107.1 . . ?
C21A C22A H22C 107.1 . . ?
C21A C22A H22D 107.1 . . ?
H22C C22A H22D 106.8 . . ?
H43C C43A H43D 107.7 . . ?
C44A C43A H43C 108.8 . . ?
C44A C43A H43D 108.8 . . ?
N8A C43A H43C 108.8 . . ?
N8A C43A H43D 108.8 . . ?
N8A C43A C44A 113.6(15) . . ?
C43A C44A H44C 108.7 . . ?
C43A C44A H44D 108.7 . . ?
H44C C44A H44D 107.6 . . ?
N9A C44A C43A 114.2(15) . . ?
N9A C44A H44C 108.7 . . ?
N9A C44A H44D 108.7 . . ?
C35 N8A C36 121.0(7) . . ?
C35 N8A C43A 123.4(9) . . ?
C36 N8A C43A 114.5(9) . . ?
C45 N9A C52 117.8(7) . . ?
C45 N9A C44A 111.4(9) . . ?
C52 N9A C44A 129.5(10) . . ?
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 C30 1.339(3) . ?
F2 C30 1.325(3) . ?
F3 C30 1.319(3) . ?
F4 C31 1.333(3) . ?
F5 C31 1.346(3) . ?
F6 C31 1.349(4) . ?
O1 C4 1.245(3) . ?
O2 C14 1.241(3) . ?
O3 C23 1.230(3) . ?
N1 C1 1.456(3) . ?
N1 C4 1.340(3) . ?
N1 H1 0.78(3) . ?
N2 C4 1.388(4) . ?
N2 C5 1.458(4) . ?
N2 C12 1.453(5) . ?
N3 C13 1.453(5) . ?
N3 C14 1.408(4) . ?
N3 C21 1.458(5) . ?
N4 C14 1.344(3) . ?
N4 C15 1.457(3) . ?
N4 H4 0.89(3) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C22 1.466(5) . ?
N5 C23 1.355(3) . ?
N5 C22A 1.468(7) . ?
N6 C23 1.372(3) . ?
N6 C24 1.397(3) . ?
N6 H6 0.80(3) . ?
C1 H1A 1.0000 . ?
C1 C2 1.510(4) . ?
C1 C3 1.519(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N2A 1.422(6) . ?
C5 H5AA 0.9900 . ?
C5 H5AB 0.9900 . ?
C5 H5BC 0.9900 . ?
C5 H5BD 0.9900 . ?
C5 C6 1.517(4) . ?
C5 N2A 1.465(6) . ?
C6 C7 1.378(4) . ?
C6 C11 1.393(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.518(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N3A 1.412(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.520(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.511(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.519(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.508(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.509(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.511(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C24 C25 1.388(4) . ?
C24 C29 1.396(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(3) . ?
C26 C27 1.382(4) . ?
C26 C30 1.484(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.382(4) . ?
C28 C29 1.391(3) . ?
C28 C31 1.485(4) . ?
C29 H29 0.9500 . ?
F7 C61 1.331(3) . ?
F8 C61 1.329(3) . ?
F9 C61 1.336(3) . ?
F10 C62 1.301(4) . ?
F11 C62 1.353(4) . ?
F12 C62 1.337(4) . ?
O4 C35 1.245(3) . ?
O5 C45 1.245(3) . ?
O6 C54 1.234(3) . ?
N7 C32 1.468(3) . ?
N7 C35 1.333(4) . ?
N7 H7A 0.79(3) . ?
N8 C35 1.397(3) . ?
N8 C36 1.459(4) . ?
N8 C43 1.472(4) . ?
N9 C44 1.445(4) . ?
N9 C45 1.383(4) . ?
N9 C52 1.456(3) . ?
N10 C45 1.327(4) . ?
N10 C46 1.463(3) . ?
N10 H10A 0.80(3) . ?
N11 C53 1.453(3) . ?
N11 C54 1.344(3) . ?
N11 H11A 0.83(3) . ?
N12 C54 1.382(3) . ?
N12 C55 1.392(3) . ?
N12 H12 0.87(3) . ?
C32 H32 1.0000 . ?
C32 C33 1.514(4) . ?
C32 C34 1.515(4) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 N8A 1.396(7) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 H36C 0.9900 . ?
C36 H36D 0.9900 . ?
C36 C37 1.509(4) . ?
C36 N8A 1.408(7) . ?
C37 C38 1.377(4) . ?
C37 C42 1.390(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.394(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.372(5) . ?
C40 H40 0.9500 . ?
C40 C41 1.364(5) . ?
C41 H41 0.9500 . ?
C41 C42 1.387(5) . ?
C42 H42 0.9500 . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 C44 1.528(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 N9A 1.432(7) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C46 C47 1.496(4) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C48 1.482(4) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C49 1.495(4) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C49 C50 1.485(4) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C50 C51 1.487(4) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C52 H52C 0.9900 . ?
C52 H52D 0.9900 . ?
C52 C53 1.527(4) . ?
C52 N9A 1.452(7) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C55 C56 1.402(4) . ?
C55 C60 1.389(4) . ?
C56 H56 0.9500 . ?
C56 C57 1.384(4) . ?
C57 C58 1.384(4) . ?
C57 C61 1.495(4) . ?
C58 H58 0.9500 . ?
C58 C59 1.392(4) . ?
C59 C60 1.385(4) . ?
C59 C62 1.499(4) . ?
C60 H60 0.9500 . ?
N2A C12A 1.469(7) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C12A C13A 1.513(7) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C13A N3A 1.459(7) . ?
N3A C21A 1.461(7) . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
C21A C22A 1.512(8) . ?
C22A H22C 0.9900 . ?
C22A H22D 0.9900 . ?
C43A H43C 0.9900 . ?
C43A H43D 0.9900 . ?
C43A C44A 1.522(10) . ?
C43A N8A 1.444(8) . ?
C44A H44C 0.9900 . ?
C44A H44D 0.9900 . ?
C44A N9A 1.468(8) . ?
