#------------------------------------------------------------------------------
#$Date: 2021-11-06 22:40:57 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270497 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158329.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_7158329
loop_
_publ_author_name
'Marras, Valentina'
'Caboni, Pierluigi'
'Secci, Francesco'
'Guillot, Régis'
'Aitken, David J.'
'Frongia, Angelo'
_publ_section_title
;
 A Brønsted acid catalyzed tandem reaction for the diastereoselective
 synthesis of cyclobuta-fused tetrahydroquinoline carboxylic esters.
;
_journal_issue                   41
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8912
_journal_page_last               8916
_journal_paper_doi               10.1039/d1ob01518d
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H26 N2 O2'
_chemical_formula_sum            'C22 H26 N2 O2'
_chemical_formula_weight         350.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-31 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.5210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.1401(3)
_cell_length_b                   28.7617(7)
_cell_length_c                   11.7457(3)
_cell_measurement_reflns_used    9143
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      65.21
_cell_measurement_theta_min      3.07
_cell_volume                     3763.26(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            50526
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        65.200
_diffrn_reflns_theta_max         65.200
_diffrn_reflns_theta_min         3.073
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  0.9526
_exptl_absorpt_correction_T_min  0.9087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 5585 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     945
_refine_ls_number_reflns         12738
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0324
_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)+(0.0449P)²+0.7720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                12154
_reflns_number_total             12738
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01518d2.cif
_cod_data_source_block           3s
_cod_depositor_comments
'Adding full bibliography for 7158328--7158329.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7158329
_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_min   0.906
_shelx_estimated_absorpt_t_max   0.941
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 1.3887(3) 0.71051(9) 0.4068(3) 0.0378(7) Uani 1 1 d . . . . .
H1 H 1.414563 0.724760 0.475793 0.045 Uiso 1 1 calc R U . . .
C2 C 1.4563(3) 0.71559(10) 0.3093(4) 0.0448(9) Uani 1 1 d . . . . .
H2 H 1.528030 0.733443 0.312237 0.054 Uiso 1 1 calc R U . . .
C3 C 1.4216(3) 0.69530(10) 0.2082(3) 0.0398(7) Uani 1 1 d . . . . .
H3 H 1.469529 0.698617 0.142206 0.048 Uiso 1 1 calc R U . . .
C4 C 1.3166(2) 0.67009(9) 0.2040(3) 0.0297(6) Uani 1 1 d . . . . .
H4 H 1.291567 0.656274 0.134256 0.036 Uiso 1 1 calc R U . . .
C5 C 1.2468(2) 0.66464(8) 0.3004(2) 0.0230(5) Uani 1 1 d . . . . .
H5 H 1.174397 0.647290 0.295585 0.028 Uiso 1 1 calc R U . . .
C6 C 1.2814(2) 0.68425(8) 0.4045(2) 0.0245(6) Uani 1 1 d . . . . .
C7 C 1.1199(2) 0.64478(8) 0.5138(2) 0.0212(5) Uani 1 1 d . . . . .
C8 C 1.0934(3) 0.63519(10) 0.6417(2) 0.0332(7) Uani 1 1 d . . . . .
H8A H 1.135085 0.656850 0.694336 0.040 Uiso 1 1 calc R U . . .
H8B H 1.006707 0.633559 0.658940 0.040 Uiso 1 1 calc R U . . .
C9 C 1.1541(3) 0.58711(10) 0.6338(2) 0.0314(6) Uani 1 1 d . . . . .
H9A H 1.101125 0.561012 0.655573 0.038 Uiso 1 1 calc R U . . .
H9B H 1.232106 0.585279 0.674576 0.038 Uiso 1 1 calc R U . . .
C10 C 1.1662(2) 0.59337(8) 0.50343(19) 0.0183(5) Uani 1 1 d . . . . .
H10 H 1.251759 0.592007 0.478733 0.022 Uiso 1 1 calc R U . . .
C11 C 1.0860(2) 0.56204(8) 0.43184(19) 0.0162(5) Uani 1 1 d . . . . .
H11 H 1.105591 0.567232 0.349902 0.019 Uiso 1 1 calc R U . . .
C12 C 0.9294(2) 0.61961(9) 0.4162(2) 0.0209(5) Uani 1 1 d . . . . .
C13 C 1.0088(2) 0.65586(8) 0.4434(2) 0.0201(5) Uani 1 1 d . . . . .
C14 C 0.9799(2) 0.70077(9) 0.4088(2) 0.0252(5) Uani 1 1 d . . . . .
H14 H 1.034430 0.725408 0.424364 0.030 Uiso 1 1 calc R U . . .
C15 C 0.8732(2) 0.71025(9) 0.3520(2) 0.0275(6) Uani 1 1 d . . . . .
H15 H 0.855085 0.741092 0.328553 0.033 Uiso 1 1 calc R U . . .
C16 C 0.7929(2) 0.67450(10) 0.3296(2) 0.0286(6) Uani 1 1 d . . . . .
H16 H 0.718252 0.680993 0.293171 0.034 Uiso 1 1 calc R U . . .
C17 C 0.8215(2) 0.62935(10) 0.3603(2) 0.0268(6) Uani 1 1 d . . . . .
H17 H 0.767097 0.604836 0.343227 0.032 Uiso 1 1 calc R U . . .
C18 C 1.1036(2) 0.51058(8) 0.45827(18) 0.0165(5) Uani 1 1 d . . . . .
C19 C 1.2622(2) 0.45576(8) 0.5200(2) 0.0170(5) Uani 1 1 d . . . . .
C20 C 1.1935(2) 0.43789(10) 0.6216(2) 0.0285(6) Uani 1 1 d . . . . .
H20A H 1.191708 0.461913 0.680703 0.043 Uiso 1 1 calc R U . . .
H20B H 1.233204 0.410010 0.651709 0.043 Uiso 1 1 calc R U . . .
H20C H 1.111278 0.430163 0.598152 0.043 Uiso 1 1 calc R U . . .
C21 C 1.2557(2) 0.42381(9) 0.4181(2) 0.0222(5) Uani 1 1 d . . . . .
H21A H 1.171555 0.419022 0.396027 0.033 Uiso 1 1 calc R U . . .
H21B H 1.292337 0.393836 0.437546 0.033 Uiso 1 1 calc R U . . .
H21C H 1.299047 0.437840 0.354463 0.033 Uiso 1 1 calc R U . . .
C22 C 1.3915(2) 0.46585(9) 0.5529(2) 0.0256(5) Uani 1 1 d . . . . .
H22A H 1.433269 0.479374 0.487699 0.038 Uiso 1 1 calc R U . . .
H22B H 1.431342 0.436873 0.575598 0.038 Uiso 1 1 calc R U . . .
H22C H 1.393528 0.487824 0.616643 0.038 Uiso 1 1 calc R U . . .
C23 C 0.8802(2) 0.70780(8) 0.7885(2) 0.0263(5) Uani 1 1 d . . . . .
H23 H 0.899793 0.717511 0.713583 0.032 Uiso 1 1 calc R U . . .
C24 C 0.9581(2) 0.71719(9) 0.8770(3) 0.0316(6) Uani 1 1 d . . . . .
H24 H 1.031253 0.732988 0.862297 0.038 Uiso 1 1 calc R U . . .
C25 C 0.9315(2) 0.70394(9) 0.9873(3) 0.0336(6) Uani 1 1 d . . . . .
H25 H 0.985524 0.710603 1.048213 0.040 Uiso 1 1 calc R U . . .
C26 C 0.8244(2) 0.68073(9) 1.0072(2) 0.0277(6) Uani 1 1 d . . . . .
H26 H 0.805295 0.671525 1.082617 0.033 Uiso 1 1 calc R U . . .
C27 C 0.7445(2) 0.67072(8) 0.9190(2) 0.0231(5) Uani 1 1 d . . . . .
H27 H 0.671614 0.654917 0.934457 0.028 Uiso 1 1 calc R U . . .
C28 C 0.7714(2) 0.68388(8) 0.8074(2) 0.0196(5) Uani 1 1 d . . . . .
C29 C 0.6037(2) 0.63963(8) 0.71643(19) 0.0163(5) Uani 1 1 d . . . . .
C30 C 0.6539(2) 0.58898(8) 0.73578(19) 0.0151(4) Uani 1 1 d . . . . .
H30 H 0.741536 0.589191 0.754882 0.018 Uiso 1 1 calc R U . . .
C31 C 0.6308(2) 0.57786(9) 0.6087(2) 0.0241(5) Uani 1 1 d . . . . .
H31A H 0.705183 0.574283 0.564019 0.029 Uiso 1 1 calc R U . . .
H31B H 0.576290 0.551114 0.596167 0.029 Uiso 1 1 calc R U . . .
C32 C 0.5693(2) 0.62542(8) 0.59251(19) 0.0212(5) Uani 1 1 d . . . . .
H32A H 0.481634 0.623192 0.579159 0.025 Uiso 1 1 calc R U . . .
H32B H 0.607421 0.645035 0.533757 0.025 Uiso 1 1 calc R U . . .
C33 C 0.5829(2) 0.56044(8) 0.82010(19) 0.0153(5) Uani 1 1 d . . . . .
H33 H 0.610217 0.569203 0.898533 0.018 Uiso 1 1 calc R U . . .
C34 C 0.4241(2) 0.61716(8) 0.83070(19) 0.0159(5) Uani 1 1 d . . . . .
C35 C 0.4968(2) 0.65271(8) 0.78812(19) 0.0155(4) Uani 1 1 d . . . . .
C36 C 0.4639(2) 0.69883(8) 0.8062(2) 0.0207(5) Uani 1 1 d . . . . .
H36 H 0.513509 0.723078 0.778307 0.025 Uiso 1 1 calc R U . . .
C37 C 0.3599(2) 0.70994(9) 0.8642(2) 0.0240(5) Uani 1 1 d . . . . .
H37 H 0.339184 0.741545 0.876857 0.029 Uiso 1 1 calc R U . . .
C38 C 0.2866(2) 0.67471(9) 0.9035(2) 0.0231(5) Uani 1 1 d . . . . .
H38 H 0.214189 0.682160 0.941410 0.028 Uiso 1 1 calc R U . . .
C39 C 0.3184(2) 0.62866(9) 0.8877(2) 0.0199(5) Uani 1 1 d . . . . .
H39 H 0.268063 0.604676 0.915776 0.024 Uiso 1 1 calc R U . . .
C40 C 0.60082(19) 0.50810(8) 0.80600(18) 0.0154(5) Uani 1 1 d . . . . .
C41 C 0.7582(2) 0.45107(8) 0.7564(2) 0.0191(5) Uani 1 1 d . . . . .
C42 C 0.7552(2) 0.42392(9) 0.8664(2) 0.0246(6) Uani 1 1 d . . . . .
H42A H 0.800170 0.440788 0.925357 0.037 Uiso 1 1 calc R U . . .
H42B H 0.791642 0.393295 0.854761 0.037 Uiso 1 1 calc R U . . .
H42C H 0.671742 0.420039 0.890387 0.037 Uiso 1 1 calc R U . . .
C43 C 0.6857(2) 0.42816(10) 0.6618(2) 0.0281(6) Uani 1 1 d . . . . .
H43A H 0.604258 0.421869 0.688505 0.042 Uiso 1 1 calc R U . . .
H43B H 0.724213 0.398881 0.640019 0.042 Uiso 1 1 calc R U . . .
H43C H 0.682010 0.448954 0.595756 0.042 Uiso 1 1 calc R U . . .
C44 C 0.8857(2) 0.45977(10) 0.7184(3) 0.0309(6) Uani 1 1 d . . . . .
H44A H 0.884650 0.478291 0.648327 0.046 Uiso 1 1 calc R U . . .
H44B H 0.925521 0.429975 0.704028 0.046 Uiso 1 1 calc R U . . .
H44C H 0.929566 0.476665 0.778071 0.046 Uiso 1 1 calc R U . . .
C45 C 0.5164(2) 0.33555(9) 0.4592(2) 0.0232(5) Uani 1 1 d . . . . .
H45 H 0.590631 0.351745 0.462623 0.028 Uiso 1 1 calc R U . . .
C46 C 0.4507(2) 0.32899(9) 0.5578(2) 0.0281(6) Uani 1 1 d . . . . .
H46 H 0.480769 0.340827 0.628010 0.034 Uiso 1 1 calc R U . . .
C47 C 0.3422(3) 0.30551(10) 0.5558(3) 0.0369(7) Uani 1 1 d . . . . .
H47 H 0.297592 0.301322 0.623580 0.044 Uiso 1 1 calc R U . . .
C48 C 0.3000(2) 0.28826(10) 0.4528(3) 0.0379(7) Uani 1 1 d . . . . .
H48 H 0.226243 0.271722 0.450132 0.045 Uiso 1 1 calc R U . . .
C49 C 0.3642(2) 0.29483(9) 0.3535(3) 0.0328(6) Uani 1 1 d . . . . .
H49 H 0.333348 0.283109 0.283545 0.039 Uiso 1 1 calc R U . . .
C50 C 0.4741(2) 0.31855(8) 0.3551(2) 0.0241(5) Uani 1 1 d . . . . .
C51 C 0.6314(2) 0.35793(8) 0.2403(2) 0.0228(5) Uani 1 1 d . . . . .
C52 C 0.6548(3) 0.36783(10) 0.1112(2) 0.0375(7) Uani 1 1 d . . . . .
H52A H 0.740788 0.366644 0.090688 0.045 Uiso 1 1 calc R U . . .
H52B H 0.606188 0.348226 0.059090 0.045 Uiso 1 1 calc R U . . .
C53 C 0.6060(4) 0.41770(11) 0.1241(2) 0.0552(11) Uani 1 1 d . . . . .
H53A H 0.666149 0.442079 0.107798 0.066 Uiso 1 1 calc R U . . .
H53B H 0.530767 0.423341 0.080783 0.066 Uiso 1 1 calc R U . . .
C54 C 0.5864(2) 0.40968(8) 0.25132(19) 0.0209(5) Uani 1 1 d . . . . .
H54 H 0.499049 0.410795 0.270166 0.025 Uiso 1 1 calc R U . . .
C55 C 0.6591(2) 0.44003(8) 0.3316(2) 0.0199(5) Uani 1 1 d . . . . .
H55 H 0.632219 0.433733 0.411146 0.024 Uiso 1 1 calc R U . . .
C56 C 0.8185(2) 0.38291(9) 0.3452(2) 0.0255(6) Uani 1 1 d . . . . .
C57 C 0.7445(2) 0.34664(8) 0.3064(2) 0.0218(5) Uani 1 1 d . . . . .
C58 C 0.7810(3) 0.30103(9) 0.3240(2) 0.0282(6) Uani 1 1 d . . . . .
H58 H 0.730150 0.276328 0.300080 0.034 Uiso 1 1 calc R U . . .
C59 C 0.8899(3) 0.29076(10) 0.3757(3) 0.0330(7) Uani 1 1 d . . . . .
H59 H 0.914709 0.259364 0.384756 0.040 Uiso 1 1 calc R U . . .
C60 C 0.9622(2) 0.32667(11) 0.4139(3) 0.0420(8) Uani 1 1 d . . . . .
H60 H 1.036883 0.319862 0.449798 0.050 Uiso 1 1 calc R U . . .
C61 C 0.9267(2) 0.37243(11) 0.4003(3) 0.0403(8) Uani 1 1 d . . . . .
H61 H 0.976085 0.396827 0.428615 0.048 Uiso 1 1 calc R U . . .
C62 C 0.6423(2) 0.49152(8) 0.30738(19) 0.0170(5) Uani 1 1 d . . . . .
C63 C 0.4849(2) 0.54667(8) 0.24419(19) 0.0162(5) Uani 1 1 d . . . . .
C64 C 0.5562(2) 0.56563(10) 0.1454(2) 0.0281(6) Uani 1 1 d . . . . .
H64A H 0.638355 0.572472 0.170871 0.042 Uiso 1 1 calc R U . . .
H64B H 0.518286 0.594192 0.117224 0.042 Uiso 1 1 calc R U . . .
H64C H 0.558169 0.542507 0.084179 0.042 Uiso 1 1 calc R U . . .
C65 C 0.4902(2) 0.57743(9) 0.3489(2) 0.0195(5) Uani 1 1 d . . . . .
H65A H 0.446769 0.562476 0.411113 0.029 Uiso 1 1 calc R U . . .
H65B H 0.453207 0.607535 0.331466 0.029 Uiso 1 1 calc R U . . .
H65C H 0.574183 0.582155 0.371721 0.029 Uiso 1 1 calc R U . . .
C66 C 0.3560(2) 0.53699(9) 0.2087(2) 0.0266(6) Uani 1 1 d . . . . .
H66A H 0.355081 0.516725 0.141626 0.040 Uiso 1 1 calc R U . . .
H66B H 0.315717 0.566361 0.190244 0.040 Uiso 1 1 calc R U . . .
H66C H 0.314063 0.521644 0.271293 0.040 Uiso 1 1 calc R U . . .
C67A C -0.0319(3) 0.31995(15) 0.9594(3) 0.0293(8) Uani 0.485(5) 1 d G . P A 1
C68A C 0.0019(3) 0.32960(14) 0.8482(3) 0.0293(8) Uani 0.485(5) 1 d G . P A 1
H68A H 0.075025 0.345488 0.834090 0.035 Uiso 0.485(5) 1 calc R U P A 1
C69A C -0.0714(3) 0.31602(13) 0.7578(2) 0.0293(8) Uani 0.485(5) 1 d G . P A 1
H69A H -0.048287 0.322616 0.681781 0.035 Uiso 0.485(5) 1 calc R U P A 1
C70A C -0.1784(3) 0.29278(14) 0.7784(3) 0.0293(8) Uani 0.485(5) 1 d G . P A 1
H70A H -0.228424 0.283490 0.716600 0.035 Uiso 0.485(5) 1 calc R U P A 1
C71A C -0.2121(3) 0.28312(13) 0.8896(3) 0.0293(8) Uani 0.485(5) 1 d G . P A 1
H71A H -0.285250 0.267236 0.903727 0.035 Uiso 0.485(5) 1 calc R U P A 1
C72A C -0.1389(3) 0.29671(13) 0.9801(3) 0.0293(8) Uani 0.485(5) 1 d G . P A 1
H72A H -0.161939 0.290108 1.056038 0.035 Uiso 0.485(5) 1 calc R U P A 1
C73 C 0.1282(2) 0.36347(8) 1.0480(2) 0.0183(3) Uani 1 1 d . . . . .
C74A C 0.1710(6) 0.3799(3) 1.1747(6) 0.0183(3) Uani 0.485(5) 1 d . . P A 1
H74A H 0.123846 0.365477 1.236383 0.022 Uiso 0.485(5) 1 calc R U P A 1
H74B H 0.258026 0.375691 1.188756 0.022 Uiso 0.485(5) 1 calc R U P A 1
C75A C 0.1407(8) 0.4237(4) 1.1546(9) 0.0183(3) Uani 0.485(5) 1 d . . P A 1
H75A H 0.210930 0.444800 1.155113 0.022 Uiso 0.485(5) 1 calc R U P A 1
H75B H 0.079153 0.435223 1.207888 0.022 Uiso 0.485(5) 1 calc R U P A 1
C76 C 0.0886(2) 0.41521(8) 1.0304(2) 0.0183(3) Uani 1 1 d . . . . .
H76 H -0.000552 0.419043 1.025593 0.022 Uiso 1 1 calc R U . A 1
C77 C 0.1548(2) 0.44188(8) 0.9383(2) 0.0192(5) Uani 1 1 d . . . . .
H77 H 0.120334 0.432599 0.862744 0.023 Uiso 1 1 calc R U . . .
C78 C 0.3131(2) 0.38336(8) 0.93410(19) 0.0171(5) Uani 1 1 d . . . . .
C79 C 0.2406(2) 0.34967(8) 0.98634(19) 0.0163(5) Uani 1 1 d . . . . .
C80 C 0.2788(2) 0.30359(9) 0.9869(2) 0.0260(6) Uani 1 1 d . . . . .
H80 H 0.231203 0.280615 1.023040 0.031 Uiso 1 1 calc R U . . .
C81 C 0.3850(3) 0.29076(10) 0.9357(3) 0.0337(6) Uani 1 1 d . . . . .
H81 H 0.409988 0.259182 0.936980 0.040 Uiso 1 1 calc R U . . .
C82 C 0.4549(2) 0.32402(10) 0.8824(3) 0.0297(6) Uani 1 1 d . . . . .
H82 H 0.527571 0.315191 0.846631 0.036 Uiso 1 1 calc R U . . .
C83 C 0.4189(2) 0.37009(9) 0.8814(2) 0.0229(6) Uani 1 1 d . . . . .
H83 H 0.466819 0.392765 0.844519 0.027 Uiso 1 1 calc R U . . .
C84 C 0.1408(2) 0.49425(8) 0.95095(19) 0.0162(5) Uani 1 1 d . . . . .
C85 C -0.0137(2) 0.55275(8) 0.9993(2) 0.0161(5) Uani 1 1 d . . . . .
C86 C -0.1419(2) 0.54546(9) 1.0373(2) 0.0257(5) Uani 1 1 d . . . . .
H86A H -0.186526 0.528570 0.978167 0.039 Uiso 1 1 calc R U . . .
H86B H -0.179892 0.575699 1.050374 0.039 Uiso 1 1 calc R U . . .
H86C H -0.142091 0.527405 1.108086 0.039 Uiso 1 1 calc R U . . .
C87 C 0.0597(2) 0.57634(9) 1.0920(2) 0.0233(5) Uani 1 1 d . . . . .
H87A H 0.062428 0.556431 1.159647 0.035 Uiso 1 1 calc R U . . .
H87B H 0.022765 0.606190 1.111320 0.035 Uiso 1 1 calc R U . . .
H87C H 0.141523 0.581632 1.064785 0.035 Uiso 1 1 calc R U . . .
C88 C -0.0096(2) 0.57849(8) 0.8866(2) 0.0199(5) Uani 1 1 d . . . . .
H88A H 0.073981 0.581538 0.862344 0.030 Uiso 1 1 calc R U . . .
H88B H -0.044903 0.609463 0.895604 0.030 Uiso 1 1 calc R U . . .
H88C H -0.055208 0.561076 0.828962 0.030 Uiso 1 1 calc R U . . .
N1 N 1.2134(2) 0.67987(7) 0.5017(2) 0.0275(5) Uani 1 1 d . . . . .
N2 N 0.95965(18) 0.57378(7) 0.44841(19) 0.0227(4) Uani 1 1 d . . . . .
N3 N 0.69544(17) 0.67554(7) 0.71551(18) 0.0192(4) Uani 1 1 d . . . . .
N4 N 0.45501(17) 0.57065(7) 0.81060(18) 0.0179(4) Uani 1 1 d . . . . .
N5 N 0.5388(2) 0.32300(7) 0.25386(18) 0.0263(5) Uani 1 1 d . . . . .
N6 N 0.7853(2) 0.42919(8) 0.3246(2) 0.0331(6) Uani 1 1 d . . . . .
N7B N 0.0261(4) 0.32926(16) 1.0168(4) 0.0183(3) Uani 0.515(5) 1 d . . P A 2
H7B H -0.002523 0.312620 1.073274 0.022 Uiso 0.515(5) 1 calc R U P A 2
N8 N 0.28067(19) 0.43036(7) 0.9394(2) 0.0242(5) Uani 1 1 d . . . . .
O1 O 1.02462(15) 0.48203(6) 0.45051(16) 0.0263(4) Uani 1 1 d . . . . .
O2 O 1.21758(14) 0.50262(5) 0.48724(13) 0.0166(3) Uani 1 1 d . . . . .
O3 O 0.52335(15) 0.47983(6) 0.82350(15) 0.0219(4) Uani 1 1 d . . . . .
O4 O 0.71363(14) 0.49910(5) 0.77607(13) 0.0180(3) Uani 1 1 d . . . . .
O5 O 0.72019(15) 0.52012(6) 0.31939(16) 0.0261(4) Uani 1 1 d . . . . .
O6 O 0.52932(14) 0.49949(5) 0.27441(13) 0.0182(3) Uani 1 1 d . . . . .
O7 O 0.21919(14) 0.52177(6) 0.93038(14) 0.0218(4) Uani 1 1 d . . . . .
O8 O 0.02932(14) 0.50419(5) 0.98271(14) 0.0191(3) Uani 1 1 d . . . . .
C70B C -0.1374(3) 0.30659(12) 0.7006(3) 0.0312(8) Uani 0.515(5) 1 d G . P A 2
H70B H -0.175488 0.301466 0.628980 0.037 Uiso 0.515(5) 1 calc R U P A 2
C72B C -0.1884(2) 0.28905(12) 0.7993(3) 0.0312(8) Uani 0.515(5) 1 d G . P A 2
H72B H -0.261237 0.271952 0.795131 0.037 Uiso 0.515(5) 1 calc R U P A 2
C71B C -0.1327(3) 0.29655(12) 0.9041(3) 0.0312(8) Uani 0.515(5) 1 d G . P A 2
H71B H -0.167513 0.284564 0.971536 0.037 Uiso 0.515(5) 1 calc R U P A 2
C67B C -0.0261(3) 0.32157(13) 0.9102(2) 0.0312(8) Uani 0.515(5) 1 d G . P A 2
C69B C 0.0248(3) 0.33910(13) 0.8115(3) 0.0312(8) Uani 0.515(5) 1 d G . P A 2
H69B H 0.097713 0.356203 0.815644 0.037 Uiso 0.515(5) 1 calc R U P A 2
C68B C -0.0308(3) 0.33161(12) 0.7067(3) 0.0312(8) Uani 0.515(5) 1 d G . P A 2
H68B H 0.003990 0.343593 0.639237 0.037 Uiso 0.515(5) 1 calc R U P A 2
N7A N 0.0407(4) 0.32987(17) 1.0555(5) 0.0183(3) Uani 0.485(5) 1 d . . P A 1
H7A H 0.030115 0.314682 1.119624 0.022 Uiso 0.485(5) 1 calc R U P A 1
C74B C 0.1328(6) 0.3704(2) 1.1749(5) 0.0239(14) Uani 0.515(5) 1 d . . P A 2
H74C H 0.211600 0.362882 1.209877 0.029 Uiso 0.515(5) 1 calc R U P A 2
H74D H 0.066721 0.354902 1.215934 0.029 Uiso 0.515(5) 1 calc R U P A 2
C75B C 0.1103(7) 0.4284(3) 1.1534(7) 0.0271(17) Uani 0.515(5) 1 d . . P A 2
H75C H 0.039211 0.441232 1.192365 0.032 Uiso 0.515(5) 1 calc R U P A 2
H75D H 0.182346 0.447898 1.166499 0.032 Uiso 0.515(5) 1 calc R U P A 2
H400 H 0.410(2) 0.5501(11) 0.847(2) 0.019(7) Uiso 1 1 d . . . . .
H600 H 0.829(3) 0.4485(14) 0.356(3) 0.039(10) Uiso 1 1 d . . . . .
H100 H 1.252(3) 0.6882(12) 0.563(3) 0.036(9) Uiso 1 1 d . . . . .
H500 H 0.494(3) 0.3185(11) 0.190(3) 0.036(9) Uiso 1 1 d . . . . .
H200 H 0.910(3) 0.5506(12) 0.417(3) 0.036(9) Uiso 1 1 d . . . . .
H300 H 0.731(3) 0.6768(11) 0.645(3) 0.036(8) Uiso 1 1 d . . . . .
H800 H 0.324(3) 0.4484(11) 0.900(3) 0.026(8) 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 0.0179 0.0091 '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'
N N 0.0311 0.0181 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0495 0.0323 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
N1 C6 C5 122.5(2) . . ?
N1 C6 C1 120.2(2) . . ?
C5 C6 C1 117.3(3) . . ?
N1 C7 C13 112.4(2) . . ?
N1 C7 C8 111.0(2) . . ?
C13 C7 C8 113.7(2) . . ?
N1 C7 C10 114.1(2) . . ?
C13 C7 C10 114.98(19) . . ?
C8 C7 C10 88.47(18) . . ?
C9 C8 C7 90.8(2) . . ?
C9 C8 H8A 113.5 . . ?
C7 C8 H8A 113.5 . . ?
C9 C8 H8B 113.5 . . ?
C7 C8 H8B 113.5 . . ?
H8A C8 H8B 110.8 . . ?
C8 C9 C10 89.9(2) . . ?
C8 C9 H9A 113.7 . . ?
C10 C9 H9A 113.7 . . ?
C8 C9 H9B 113.7 . . ?
C10 C9 H9B 113.7 . . ?
H9A C9 H9B 110.9 . . ?
C11 C10 C9 115.0(2) . . ?
C11 C10 C7 114.21(19) . . ?
C9 C10 C7 90.07(18) . . ?
C11 C10 H10 111.9 . . ?
C9 C10 H10 111.9 . . ?
C7 C10 H10 111.9 . . ?
N2 C11 C10 110.57(19) . . ?
N2 C11 C18 108.62(19) . . ?
C10 C11 C18 112.93(18) . . ?
N2 C11 H11 108.2 . . ?
C10 C11 H11 108.2 . . ?
C18 C11 H11 108.2 . . ?
C17 C12 C13 119.9(2) . . ?
C17 C12 N2 121.1(2) . . ?
C13 C12 N2 119.0(2) . . ?
C14 C13 C12 118.7(2) . . ?
C14 C13 C7 122.7(2) . . ?
C12 C13 C7 118.6(2) . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
O1 C18 O2 126.6(2) . . ?
O1 C18 C11 123.6(2) . . ?
O2 C18 C11 109.86(18) . . ?
O2 C19 C21 109.48(18) . . ?
O2 C19 C20 110.00(18) . . ?
C21 C19 C20 113.4(2) . . ?
O2 C19 C22 101.94(18) . . ?
C21 C19 C22 110.9(2) . . ?
C20 C19 C22 110.5(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 120.9(3) . . ?
C24 C23 H23 119.6 . . ?
C28 C23 H23 119.6 . . ?
C23 C24 C25 121.0(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C26 118.8(2) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C25 C26 C27 121.2(3) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C26 C27 C28 120.1(2) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
N3 C28 C27 123.3(2) . . ?
N3 C28 C23 118.7(2) . . ?
C27 C28 C23 118.0(2) . . ?
N3 C29 C35 112.62(19) . . ?
N3 C29 C32 110.29(19) . . ?
C35 C29 C32 113.47(19) . . ?
N3 C29 C30 114.15(18) . . ?
C35 C29 C30 115.46(18) . . ?
C32 C29 C30 88.63(17) . . ?
C33 C30 C31 115.84(19) . . ?
C33 C30 C29 114.10(18) . . ?
C31 C30 C29 89.79(17) . . ?
C33 C30 H30 111.8 . . ?
C31 C30 H30 111.8 . . ?
C29 C30 H30 111.8 . . ?
C32 C31 C30 90.29(18) . . ?
C32 C31 H31A 113.6 . . ?
C30 C31 H31A 113.6 . . ?
C32 C31 H31B 113.6 . . ?
C30 C31 H31B 113.6 . . ?
H31A C31 H31B 110.9 . . ?
C31 C32 C29 90.73(17) . . ?
C31 C32 H32A 113.5 . . ?
C29 C32 H32A 113.5 . . ?
C31 C32 H32B 113.5 . . ?
C29 C32 H32B 113.5 . . ?
H32A C32 H32B 110.8 . . ?
N4 C33 C30 110.88(18) . . ?
N4 C33 C40 108.61(18) . . ?
C30 C33 C40 113.16(19) . . ?
N4 C33 H33 108.0 . . ?
C30 C33 H33 108.0 . . ?
C40 C33 H33 108.0 . . ?
C39 C34 C35 119.4(2) . . ?
C39 C34 N4 121.0(2) . . ?
C35 C34 N4 119.5(2) . . ?
C36 C35 C34 119.1(2) . . ?
C36 C35 C29 122.1(2) . . ?
C34 C35 C29 118.6(2) . . ?
C37 C36 C35 121.1(2) . . ?
C37 C36 H36 119.4 . . ?
C35 C36 H36 119.4 . . ?
C38 C37 C36 119.6(2) . . ?
C38 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
C37 C38 C39 120.3(2) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C38 C39 C34 120.5(2) . . ?
C38 C39 H39 119.8 . . ?
C34 C39 H39 119.8 . . ?
O3 C40 O4 126.3(2) . . ?
O3 C40 C33 123.5(2) . . ?
O4 C40 C33 110.15(18) . . ?
O4 C41 C42 109.76(19) . . ?
O4 C41 C44 101.98(19) . . ?
C42 C41 C44 111.5(2) . . ?
O4 C41 C43 109.94(18) . . ?
C42 C41 C43 112.7(2) . . ?
C44 C41 C43 110.4(2) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C46 C45 C50 120.5(2) . . ?
C46 C45 H45 119.7 . . ?
C50 C45 H45 119.7 . . ?
C47 C46 C45 121.2(3) . . ?
C47 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C46 C47 C48 118.6(3) . . ?
C46 C47 H47 120.7 . . ?
C48 C47 H47 120.7 . . ?
C47 C48 C49 120.8(3) . . ?
C47 C48 H48 119.6 . . ?
C49 C48 H48 119.6 . . ?
C48 C49 C50 120.9(3) . . ?
C48 C49 H49 119.6 . . ?
C50 C49 H49 119.6 . . ?
C45 C50 C49 118.0(3) . . ?
C45 C50 N5 122.7(2) . . ?
C49 C50 N5 119.3(2) . . ?
N5 C51 C57 112.7(2) . . ?
N5 C51 C52 111.0(2) . . ?
C57 C51 C52 113.0(2) . . ?
N5 C51 C54 114.7(2) . . ?
C57 C51 C54 115.2(2) . . ?
C52 C51 C54 87.93(18) . . ?
C53 C52 C51 90.7(2) . . ?
C53 C52 H52A 113.5 . . ?
C51 C52 H52A 113.5 . . ?
C53 C52 H52B 113.5 . . ?
C51 C52 H52B 113.5 . . ?
H52A C52 H52B 110.8 . . ?
C54 C53 C52 90.6(2) . . ?
C54 C53 H53A 113.5 . . ?
C52 C53 H53A 113.5 . . ?
C54 C53 H53B 113.5 . . ?
C52 C53 H53B 113.5 . . ?
H53A C53 H53B 110.8 . . ?
C55 C54 C53 116.2(2) . . ?
C55 C54 C51 115.26(19) . . ?
C53 C54 C51 90.79(19) . . ?
C55 C54 H54 111.1 . . ?
C53 C54 H54 111.1 . . ?
C51 C54 H54 111.1 . . ?
N6 C55 C54 110.8(2) . . ?
N6 C55 C62 108.6(2) . . ?
C54 C55 C62 112.38(19) . . ?
N6 C55 H55 108.3 . . ?
C54 C55 H55 108.3 . . ?
C62 C55 H55 108.3 . . ?
C61 C56 N6 120.7(3) . . ?
C61 C56 C57 119.5(2) . . ?
N6 C56 C57 119.8(2) . . ?
C58 C57 C56 118.9(2) . . ?
C58 C57 C51 121.5(2) . . ?
C56 C57 C51 119.5(2) . . ?
C59 C58 C57 121.5(3) . . ?
C59 C58 H58 119.3 . . ?
C57 C58 H58 119.3 . . ?
C60 C59 C58 119.3(3) . . ?
C60 C59 H59 120.4 . . ?
C58 C59 H59 120.4 . . ?
C59 C60 C61 120.6(3) . . ?
C59 C60 H60 119.7 . . ?
C61 C60 H60 119.7 . . ?
C60 C61 C56 120.2(3) . . ?
C60 C61 H61 119.9 . . ?
C56 C61 H61 119.9 . . ?
O5 C62 O6 126.5(2) . . ?
O5 C62 C55 123.8(2) . . ?
O6 C62 C55 109.66(19) . . ?
O6 C63 C64 109.66(18) . . ?
O6 C63 C65 109.19(18) . . ?
C64 C63 C65 113.3(2) . . ?
O6 C63 C66 102.12(18) . . ?
C64 C63 C66 110.9(2) . . ?
C65 C63 C66 111.1(2) . . ?
C63 C64 H64A 109.5 . . ?
C63 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C63 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C63 C65 H65A 109.5 . . ?
C63 C65 H65B 109.5 . . ?
H65A C65 H65B 109.5 . . ?
C63 C65 H65C 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C63 C66 H66A 109.5 . . ?
C63 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C63 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C68A C67A C72A 120.0 . . ?
C68A C67A N7A 123.6(3) . . ?
C72A C67A N7A 116.3(3) . . ?
C67A C68A C69A 120.0 . . ?
C67A C68A H68A 120.0 . . ?
C69A C68A H68A 120.0 . . ?
C70A C69A C68A 120.0 . . ?
C70A C69A H69A 120.0 . . ?
C68A C69A H69A 120.0 . . ?
C69A C70A C71A 120.0 . . ?
C69A C70A H70A 120.0 . . ?
C71A C70A H70A 120.0 . . ?
C70A C71A C72A 120.0 . . ?
C70A C71A H71A 120.0 . . ?
C72A C71A H71A 120.0 . . ?
C71A C72A C67A 120.0 . . ?
C71A C72A H72A 120.0 . . ?
C67A C72A H72A 120.0 . . ?
N7A C73 C79 116.0(3) . . ?
C74B C73 C79 119.4(3) . . ?
C74B C73 N7B 109.7(3) . . ?
C79 C73 N7B 109.4(2) . . ?
N7A C73 C76 118.5(3) . . ?
C74B C73 C76 90.6(3) . . ?
C79 C73 C76 114.98(19) . . ?
N7B C73 C76 111.6(2) . . ?
N7A C73 C74A 110.3(3) . . ?
C79 C73 C74A 106.2(3) . . ?
C76 C73 C74A 85.6(3) . . ?
C75A C74A C73 92.4(6) . . ?
C75A C74A H74A 113.2 . . ?
C73 C74A H74A 113.2 . . ?
C75A C74A H74B 113.2 . . ?
C73 C74A H74B 113.2 . . ?
H74A C74A H74B 110.6 . . ?
C74A C75A C76 96.2(7) . . ?
C74A C75A H75A 112.5 . . ?
C76 C75A H75A 112.5 . . ?
C74A C75A H75B 112.5 . . ?
C76 C75A H75B 112.5 . . ?
H75A C75A H75B 110.0 . . ?
C75B C76 C77 118.6(4) . . ?
C75B C76 C73 94.0(3) . . ?
C77 C76 C73 115.76(19) . . ?
C77 C76 C75A 113.6(4) . . ?
C73 C76 C75A 85.6(4) . . ?
C77 C76 H76 113.0 . . ?
C73 C76 H76 113.0 . . ?
C75A C76 H76 113.0 . . ?
N8 C77 C84 109.08(19) . . ?
N8 C77 C76 110.82(19) . . ?
C84 C77 C76 112.26(19) . . ?
N8 C77 H77 108.2 . . ?
C84 C77 H77 108.2 . . ?
C76 C77 H77 108.2 . . ?
C83 C78 N8 120.3(2) . . ?
C83 C78 C79 119.8(2) . . ?
N8 C78 C79 119.8(2) . . ?
C80 C79 C78 118.8(2) . . ?
C80 C79 C73 120.3(2) . . ?
C78 C79 C73 120.8(2) . . ?
C81 C80 C79 121.0(2) . . ?
C81 C80 H80 119.5 . . ?
C79 C80 H80 119.5 . . ?
C80 C81 C82 119.9(2) . . ?
C80 C81 H81 120.0 . . ?
C82 C81 H81 120.0 . . ?
C83 C82 C81 120.0(2) . . ?
C83 C82 H82 120.0 . . ?
C81 C82 H82 120.0 . . ?
C82 C83 C78 120.4(2) . . ?
C82 C83 H83 119.8 . . ?
C78 C83 H83 119.8 . . ?
O7 C84 O8 126.5(2) . . ?
O7 C84 C77 123.8(2) . . ?
O8 C84 C77 109.65(19) . . ?
O8 C85 C86 102.37(18) . . ?
O8 C85 C87 109.93(18) . . ?
C86 C85 C87 110.8(2) . . ?
O8 C85 C88 109.30(18) . . ?
C86 C85 C88 111.2(2) . . ?
C87 C85 C88 112.8(2) . . ?
C85 C86 H86A 109.5 . . ?
C85 C86 H86B 109.5 . . ?
H86A C86 H86B 109.5 . . ?
C85 C86 H86C 109.5 . . ?
H86A C86 H86C 109.5 . . ?
H86B C86 H86C 109.5 . . ?
C85 C87 H87A 109.5 . . ?
C85 C87 H87B 109.5 . . ?
H87A C87 H87B 109.5 . . ?
C85 C87 H87C 109.5 . . ?
H87A C87 H87C 109.5 . . ?
H87B C87 H87C 109.5 . . ?
C85 C88 H88A 109.5 . . ?
C85 C88 H88B 109.5 . . ?
H88A C88 H88B 109.5 . . ?
C85 C88 H88C 109.5 . . ?
H88A C88 H88C 109.5 . . ?
H88B C88 H88C 109.5 . . ?
C6 N1 C7 122.8(2) . . ?
C6 N1 H100 113(2) . . ?
C7 N1 H100 117(2) . . ?
C12 N2 C11 114.06(19) . . ?
C12 N2 H200 115(2) . . ?
C11 N2 H200 110.5(19) . . ?
C28 N3 C29 122.79(19) . . ?
C28 N3 H300 115(2) . . ?
C29 N3 H300 110(2) . . ?
C34 N4 C33 114.89(19) . . ?
C34 N4 H400 114.4(18) . . ?
C33 N4 H400 112.4(18) . . ?
C50 N5 C51 121.9(2) . . ?
C50 N5 H500 114(2) . . ?
C51 N5 H500 113(2) . . ?
C56 N6 C55 116.8(2) . . ?
C56 N6 H600 114(3) . . ?
C55 N6 H600 114(2) . . ?
C67B N7B C73 127.9(4) . . ?
C67B N7B H7B 116.1 . . ?
C73 N7B H7B 116.1 . . ?
C78 N8 C77 118.2(2) . . ?
C78 N8 H800 115(2) . . ?
C77 N8 H800 114(2) . . ?
C18 O2 C19 122.54(17) . . ?
C40 O4 C41 122.54(17) . . ?
C62 O6 C63 122.51(17) . . ?
C84 O8 C85 122.70(17) . . ?
C72B C70B C68B 120.0 . . ?
C72B C70B H70B 120.0 . . ?
C68B C70B H70B 120.0 . . ?
C71B C72B C70B 120.0 . . ?
C71B C72B H72B 120.0 . . ?
C70B C72B H72B 120.0 . . ?
C67B C71B C72B 120.0 . . ?
C67B C71B H71B 120.0 . . ?
C72B C71B H71B 120.0 . . ?
C71B C67B C69B 120.0 . . ?
C71B C67B N7B 118.5(3) . . ?
C69B C67B N7B 121.4(3) . . ?
C68B C69B C67B 120.0 . . ?
C68B C69B H69B 120.0 . . ?
C67B C69B H69B 120.0 . . ?
C69B C68B C70B 120.0 . . ?
C69B C68B H68B 120.0 . . ?
C70B C68B H68B 120.0 . . ?
C73 N7A C67A 119.5(4) . . ?
C73 N7A H7A 120.3 . . ?
C67A N7A H7A 120.3 . . ?
C73 C74B C75B 88.8(4) . . ?
C73 C74B H74C 113.8 . . ?
C75B C74B H74C 113.8 . . ?
C73 C74B H74D 113.8 . . ?
C75B C74B H74D 113.8 . . ?
H74C C74B H74D 111.1 . . ?
C76 C75B C74B 85.3(5) . . ?
C76 C75B H75C 114.4 . . ?
C74B C75B H75C 114.4 . . ?
C76 C75B H75D 114.4 . . ?
C74B C75B H75D 114.4 . . ?
H75C C75B H75D 111.6 . . ?
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
C1 C2 1.385(5) . ?
C1 C6 1.414(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.382(4) . ?
C7 N1 1.458(3) . ?
C7 C13 1.516(3) . ?
C7 C8 1.558(3) . ?
C7 C10 1.571(3) . ?
C8 C9 1.543(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.548(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.517(3) . ?
C10 H10 1.0000 . ?
C11 N2 1.462(3) . ?
C11 C18 1.524(3) . ?
C11 H11 1.0000 . ?
C12 C17 1.393(4) . ?
C12 C13 1.402(4) . ?
C12 N2 1.412(3) . ?
C13 C14 1.391(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 O1 1.207(3) . ?
C18 O2 1.331(3) . ?
C19 O2 1.486(3) . ?
C19 C21 1.510(3) . ?
C19 C20 1.513(3) . ?
C19 C22 1.517(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.375(4) . ?
C23 C28 1.413(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.389(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.399(4) . ?
C27 H27 0.9500 . ?
C28 N3 1.386(3) . ?
C29 N3 1.453(3) . ?
C29 C35 1.512(3) . ?
C29 C32 1.556(3) . ?
C29 C30 1.576(3) . ?
C30 C33 1.515(3) . ?
C30 C31 1.546(3) . ?
C30 H30 1.0000 . ?
C31 C32 1.541(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 N4 1.458(3) . ?
C33 C40 1.528(3) . ?
C33 H33 1.0000 . ?
C34 C39 1.399(3) . ?
C34 C35 1.400(3) . ?
C34 N4 1.402(3) . ?
C35 C36 1.393(3) . ?
C36 C37 1.386(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.383(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.384(4) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 O3 1.205(3) . ?
C40 O4 1.333(3) . ?
C41 O4 1.487(3) . ?
C41 C42 1.510(4) . ?
C41 C44 1.515(3) . ?
C41 C43 1.518(3) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 C46 1.389(4) . ?
C45 C50 1.395(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.384(4) . ?
C46 H46 0.9500 . ?
C47 C48 1.386(5) . ?
C47 H47 0.9500 . ?
C48 C49 1.386(4) . ?
C48 H48 0.9500 . ?
C49 C50 1.401(4) . ?
C49 H49 0.9500 . ?
C50 N5 1.402(4) . ?
C51 N5 1.450(3) . ?
C51 C57 1.509(3) . ?
C51 C52 1.567(3) . ?
C51 C54 1.576(3) . ?
C52 C53 1.542(4) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.529(4) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 C55 1.515(3) . ?
C54 H54 1.0000 . ?
C55 N6 1.444(3) . ?
C55 C62 1.519(3) . ?
C55 H55 1.0000 . ?
C56 C61 1.395(4) . ?
C56 N6 1.402(3) . ?
C56 C57 1.404(4) . ?
C57 C58 1.389(4) . ?
C58 C59 1.383(4) . ?
C58 H58 0.9500 . ?
C59 C60 1.382(5) . ?
C59 H59 0.9500 . ?
C60 C61 1.383(4) . ?
C60 H60 0.9500 . ?
C61 H61 0.9500 . ?
C62 O5 1.203(3) . ?
C62 O6 1.333(3) . ?
C63 O6 1.486(3) . ?
C63 C64 1.514(3) . ?
C63 C65 1.515(3) . ?
C63 C66 1.517(3) . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C65 H65C 0.9800 . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?
C67A C68A 1.3900 . ?
C67A C72A 1.3900 . ?
C67A N7A 1.411(6) . ?
C68A C69A 1.3900 . ?
C68A H68A 0.9500 . ?
C69A C70A 1.3900 . ?
C69A H69A 0.9500 . ?
C70A C71A 1.3900 . ?
C70A H70A 0.9500 . ?
C71A C72A 1.3900 . ?
C71A H71A 0.9500 . ?
C72A H72A 0.9500 . ?
C73 N7A 1.376(5) . ?
C73 C74B 1.504(6) . ?
C73 C79 1.505(3) . ?
C73 N7B 1.545(5) . ?
C73 C76 1.565(3) . ?
C73 C74A 1.629(8) . ?
C74A C75A 1.323(13) . ?
C74A H74A 0.9900 . ?
C74A H74B 0.9900 . ?
C75A C76 1.584(11) . ?
C75A H75A 0.9900 . ?
C75A H75B 0.9900 . ?
C76 C75B 1.511(9) . ?
C76 C77 1.522(3) . ?
C76 H76 1.0000 . ?
C77 N8 1.441(3) . ?
C77 C84 1.522(3) . ?
C77 H77 1.0000 . ?
C78 C83 1.390(3) . ?
C78 N8 1.401(3) . ?
C78 C79 1.405(3) . ?
C79 C80 1.392(3) . ?
C80 C81 1.382(4) . ?
C80 H80 0.9500 . ?
C81 C82 1.387(4) . ?
C81 H81 0.9500 . ?
C82 C83 1.385(4) . ?
C82 H82 0.9500 . ?
C83 H83 0.9500 . ?
C84 O7 1.205(3) . ?
C84 O8 1.331(3) . ?
C85 O8 1.490(3) . ?
C85 C86 1.514(3) . ?
C85 C87 1.516(3) . ?
C85 C88 1.518(3) . ?
C86 H86A 0.9800 . ?
C86 H86B 0.9800 . ?
C86 H86C 0.9800 . ?
C87 H87A 0.9800 . ?
C87 H87B 0.9800 . ?
C87 H87C 0.9800 . ?
C88 H88A 0.9800 . ?
C88 H88B 0.9800 . ?
C88 H88C 0.9800 . ?
N1 H100 0.87(3) . ?
N2 H200 0.94(3) . ?
N3 H300 0.92(3) . ?
N4 H400 0.89(3) . ?
N5 H500 0.90(3) . ?
N6 H600 0.82(4) . ?
N7B C67B 1.394(5) . ?
N7B H7B 0.8800 . ?
N8 H800 0.85(3) . ?
C70B C72B 1.3900 . ?
C70B C68B 1.3900 . ?
C70B H70B 0.9500 . ?
C72B C71B 1.3900 . ?
C72B H72B 0.9500 . ?
C71B C67B 1.3900 . ?
C71B H71B 0.9500 . ?
C67B C69B 1.3900 . ?
C69B C68B 1.3900 . ?
C69B H69B 0.9500 . ?
C68B H68B 0.9500 . ?
N7A H7A 0.8800 . ?
C74B C75B 1.704(10) . ?
C74B H74C 0.9900 . ?
C74B H74D 0.9900 . ?
C75B H75C 0.9900 . ?
C75B H75D 0.9900 . ?
