#------------------------------------------------------------------------------
#$Date: 2023-12-05 06:10:03 +0200 (Tue, 05 Dec 2023) $
#$Revision: 288029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247831.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_7247831
loop_
_publ_author_name
'Amiri, Kamran'
'Nayebzadeh, Behrouz'
'Kamangar, Mohammad'
'Babazadeh, Mohammad'
'Ariafard, Alireza'
'Shiri, Farshad'
'Rominger, Frank'
'Balalaie, Saeed'
_publ_section_title
;
 Synthesis of a fused N-bridged [3.3.1]nonadiquinoline multicyclic
 skeleton via a metal-free formal [4 + 2]
 cycloaddition/Mannich/dearomatization domino reaction
;
_journal_issue                   22
_journal_name_full               'Green Chemistry'
_journal_page_first              9203
_journal_page_last               9208
_journal_paper_doi               10.1039/D3GC03026A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C50 H33 N3 O2'
_chemical_formula_weight         707.79
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-16 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   39.4459(15)
_cell_length_b                   39.4459(15)
_cell_length_c                   12.5093(8)
_cell_measurement_reflns_used    4935
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.82
_cell_measurement_theta_min      2.27
_cell_volume                     16856.5(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34031
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.108
_diffrn_reflns_theta_max         24.108
_diffrn_reflns_theta_min         2.018
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9576
_exptl_absorpt_correction_T_min  0.9297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             6660
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         5968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0526
_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)+(0.0459P)²+24.3374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1369
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3507
_reflns_number_total             5968
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3gc03026a2.cif
_cod_data_source_block           sba191_sq
_cod_original_cell_volume        16856.5(17)
_cod_database_code               7247831
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
N1 N 0.56374(6) 0.73941(6) 0.68421(17) 0.0323(6) Uani 1 1 d . . . . .
C11 C 0.57070(8) 0.77448(8) 0.7427(2) 0.0332(7) Uani 1 1 d . . . . .
H11 H 0.576633 0.771743 0.818913 0.040 Uiso 1 1 calc R U . . .
C12 C 0.53603(8) 0.78173(8) 0.7404(2) 0.0331(7) Uani 1 1 d . . . . .
C13 C 0.50961(8) 0.76536(8) 0.6554(2) 0.0333(7) Uani 1 1 d . . . . .
N14 N 0.47762(7) 0.76988(7) 0.6496(2) 0.0365(6) Uani 1 1 d . . . . .
H14 H 0.4780(8) 0.7868(8) 0.706(2) 0.044 Uiso 1 1 d . U . . .
C15 C 0.44933(8) 0.75342(8) 0.5720(2) 0.0384(7) Uani 1 1 d . . . . .
C16 C 0.41785(9) 0.76033(9) 0.5719(3) 0.0520(9) Uani 1 1 d . . . . .
H16 H 0.415739 0.776085 0.626002 0.062 Uiso 1 1 calc R U . . .
C17 C 0.39012(10) 0.74424(10) 0.4935(3) 0.0668(11) Uani 1 1 d . . . . .
H17 H 0.368808 0.749050 0.492977 0.080 Uiso 1 1 calc R U . . .
C18 C 0.39279(10) 0.72092(11) 0.4144(3) 0.0676(11) Uani 1 1 d . . . . .
H18 H 0.373351 0.709974 0.360229 0.081 Uiso 1 1 calc R U . . .
C19 C 0.42336(9) 0.71362(9) 0.4142(3) 0.0523(9) Uani 1 1 d . . . . .
H19 H 0.424984 0.697638 0.359967 0.063 Uiso 1 1 calc R U . . .
C20 C 0.45232(8) 0.72973(8) 0.4941(2) 0.0390(8) Uani 1 1 d . . . . .
C21 C 0.48542(8) 0.72404(8) 0.4986(2) 0.0347(7) Uani 1 1 d . . . . .
H21 H 0.487551 0.707253 0.447968 0.042 Uiso 1 1 calc R U . . .
C22 C 0.51367(8) 0.74197(8) 0.5731(2) 0.0315(7) Uani 1 1 d . . . . .
C23 C 0.55133(8) 0.74027(8) 0.5733(2) 0.0331(7) Uani 1 1 d . . . . .
H23 H 0.546464 0.715815 0.535985 0.040 Uiso 1 1 calc R U . . .
C24 C 0.58429(8) 0.77551(8) 0.5154(2) 0.0324(7) Uani 1 1 d . . . . .
C25 C 0.61104(8) 0.80732(8) 0.5797(2) 0.0325(7) Uani 1 1 d . . . . .
N26 N 0.64196(7) 0.83898(7) 0.5341(2) 0.0382(6) Uani 1 1 d . . . . .
H26 H 0.6425(8) 0.8369(8) 0.464(2) 0.046 Uiso 1 1 d . U . . .
C27 C 0.66880(8) 0.87156(8) 0.5902(2) 0.0370(7) Uani 1 1 d . . . . .
C28 C 0.69908(9) 0.90353(9) 0.5366(3) 0.0465(8) Uani 1 1 d . . . . .
H28 H 0.701408 0.903111 0.461081 0.056 Uiso 1 1 calc R U . . .
C29 C 0.72529(9) 0.93542(9) 0.5945(3) 0.0539(9) Uani 1 1 d . . . . .
H29 H 0.745781 0.957285 0.558582 0.065 Uiso 1 1 calc R U . . .
C30 C 0.72238(9) 0.93629(9) 0.7048(3) 0.0497(9) Uani 1 1 d . . . . .
H30 H 0.740806 0.958682 0.743683 0.060 Uiso 1 1 calc R U . . .
C31 C 0.69323(9) 0.90518(9) 0.7578(3) 0.0426(8) Uani 1 1 d . . . . .
H31 H 0.691590 0.905897 0.833477 0.051 Uiso 1 1 calc R U . . .
C32 C 0.66553(8) 0.87200(8) 0.7011(2) 0.0367(7) Uani 1 1 d . . . . .
C33 C 0.63378(8) 0.83877(8) 0.7512(2) 0.0364(7) Uani 1 1 d . . . . .
H33 H 0.631560 0.838149 0.826915 0.044 Uiso 1 1 calc R U . . .
C34 C 0.60670(8) 0.80805(8) 0.6932(2) 0.0321(7) Uani 1 1 d . . . . .
C40 C 0.53147(9) 0.80503(8) 0.8172(2) 0.0389(7) Uani 1 1 d . . . . .
O40 O 0.50440(6) 0.81370(6) 0.81398(17) 0.0533(6) Uani 1 1 d . . . . .
C41 C 0.55954(9) 0.82243(9) 0.9087(2) 0.0393(8) Uani 1 1 d . . . . .
C42 C 0.56289(9) 0.79926(10) 0.9862(2) 0.0482(8) Uani 1 1 d . . . . .
H42 H 0.547395 0.771571 0.981497 0.058 Uiso 1 1 calc R U . . .
C43 C 0.58868(11) 0.81619(13) 1.0706(3) 0.0665(11) Uani 1 1 d . . . . .
H43 H 0.590642 0.800073 1.123835 0.080 Uiso 1 1 calc R U . . .
C44 C 0.61132(13) 0.85594(15) 1.0777(3) 0.0839(13) Uani 1 1 d . . . . .
H44 H 0.629272 0.867375 1.135126 0.101 Uiso 1 1 calc R U . . .
C45 C 0.60821(12) 0.87948(12) 1.0018(4) 0.0805(12) Uani 1 1 d . . . . .
H45 H 0.623820 0.907141 1.007227 0.097 Uiso 1 1 calc R U . . .
C46 C 0.58225(10) 0.86277(10) 0.9174(3) 0.0583(10) Uani 1 1 d . . . . .
H46 H 0.580025 0.879061 0.865265 0.070 Uiso 1 1 calc R U . . .
C50 C 0.58658(9) 0.77801(9) 0.4035(2) 0.0398(8) Uani 1 1 d . . . . .
O50 O 0.61394(6) 0.80716(6) 0.35288(16) 0.0547(6) Uani 1 1 d . . . . .
C51 C 0.55539(9) 0.74748(10) 0.3329(2) 0.0441(8) Uani 1 1 d . . . . .
C52 C 0.54837(9) 0.70968(9) 0.3253(2) 0.0501(9) Uani 1 1 d . . . . .
H52 H 0.563428 0.701716 0.366385 0.060 Uiso 1 1 calc R U . . .
C53 C 0.51906(11) 0.68304(11) 0.2570(3) 0.0653(11) Uani 1 1 d . . . . .
H53 H 0.514464 0.657044 0.251743 0.078 Uiso 1 1 calc R U . . .
C54 C 0.49686(11) 0.69397(13) 0.1976(3) 0.0726(12) Uani 1 1 d . . . . .
H54 H 0.476811 0.675588 0.152072 0.087 Uiso 1 1 calc R U . . .
C55 C 0.50387(11) 0.73181(13) 0.2045(3) 0.0740(11) Uani 1 1 d . . . . .
H55 H 0.488709 0.739662 0.163439 0.089 Uiso 1 1 calc R U . . .
C56 C 0.53313(10) 0.75843(10) 0.2716(3) 0.0568(9) Uani 1 1 d . . . . .
H56 H 0.537985 0.784540 0.275632 0.068 Uiso 1 1 calc R U . . .
C61 C 0.54532(8) 0.70290(8) 0.7384(2) 0.0333(7) Uani 1 1 d . . . . .
C62 C 0.55568(8) 0.67497(8) 0.7078(2) 0.0365(7) Uani 1 1 d . . . . .
C63 C 0.53957(9) 0.63956(9) 0.7634(3) 0.0476(8) Uani 1 1 d . . . . .
H63 H 0.545832 0.620255 0.741661 0.057 Uiso 1 1 calc R U . . .
C64 C 0.51481(10) 0.63199(10) 0.8489(3) 0.0518(9) Uani 1 1 d . . . . .
H64 H 0.504202 0.607806 0.886089 0.062 Uiso 1 1 calc R U . . .
C65 C 0.50565(9) 0.65997(9) 0.8798(2) 0.0484(8) Uani 1 1 d . . . . .
H65 H 0.489059 0.655221 0.939685 0.058 Uiso 1 1 calc R U . . .
C66 C 0.52033(8) 0.69490(8) 0.8245(2) 0.0392(7) Uani 1 1 d . . . . .
H66 H 0.513203 0.713614 0.845882 0.047 Uiso 1 1 calc R U . . .
C67 C 0.58418(10) 0.68386(9) 0.6259(3) 0.0431(8) Uani 1 1 d . . . . .
C68 C 0.60825(10) 0.69140(9) 0.5583(3) 0.0479(8) Uani 1 1 d . . . . .
C71 C 0.63742(10) 0.70093(11) 0.4769(3) 0.0513(9) Uani 1 1 d . . . . .
C72 C 0.64965(13) 0.67467(13) 0.4503(3) 0.0841(13) Uani 1 1 d . . . . .
H72 H 0.638252 0.649839 0.484315 0.101 Uiso 1 1 calc R U . . .
C73 C 0.67865(15) 0.68471(17) 0.3736(4) 0.1064(17) Uani 1 1 d . . . . .
H73 H 0.687588 0.666977 0.357180 0.128 Uiso 1 1 calc R U . . .
C74 C 0.69434(13) 0.71962(16) 0.3219(4) 0.0918(14) Uani 1 1 d . . . . .
H74 H 0.713924 0.726067 0.269070 0.110 Uiso 1 1 calc R U . . .
C75 C 0.68201(11) 0.74536(12) 0.3459(3) 0.0697(11) Uani 1 1 d . . . . .
H75 H 0.693188 0.769887 0.310299 0.084 Uiso 1 1 calc R U . . .
C76 C 0.65315(9) 0.73587(11) 0.4223(3) 0.0583(10) Uani 1 1 d . . . . .
H76 H 0.644143 0.753657 0.437159 0.070 Uiso 1 1 calc R U . . .
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'
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
C61 N1 C11 118.6(2) . . ?
C61 N1 C23 117.7(2) . . ?
C11 N1 C23 110.8(2) . . ?
N1 C11 C34 105.9(2) . . ?
N1 C11 C12 113.8(2) . . ?
C34 C11 C12 111.4(2) . . ?
N1 C11 H11 108.5 . . ?
C34 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
C13 C12 C40 120.9(3) . . ?
C13 C12 C11 117.2(2) . . ?
C40 C12 C11 121.9(3) . . ?
N14 C13 C12 120.3(3) . . ?
N14 C13 C22 116.9(3) . . ?
C12 C13 C22 122.8(3) . . ?
C13 N14 C15 124.3(3) . . ?
C13 N14 H14 111.0(16) . . ?
C15 N14 H14 124.8(16) . . ?
N14 C15 C20 119.3(3) . . ?
N14 C15 C16 120.0(3) . . ?
C20 C15 C16 120.7(3) . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 118.5(3) . . ?
C15 C20 C21 117.8(3) . . ?
C19 C20 C21 123.7(3) . . ?
C22 C21 C20 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C13 120.1(3) . . ?
C21 C22 C23 123.1(3) . . ?
C13 C22 C23 116.8(2) . . ?
N1 C23 C22 110.2(2) . . ?
N1 C23 C24 108.9(2) . . ?
C22 C23 C24 111.4(2) . . ?
N1 C23 H23 108.8 . . ?
C22 C23 H23 108.8 . . ?
C24 C23 H23 108.8 . . ?
C50 C24 C25 120.7(3) . . ?
C50 C24 C23 122.1(3) . . ?
C25 C24 C23 117.0(2) . . ?
N26 C25 C24 120.2(2) . . ?
N26 C25 C34 117.3(3) . . ?
C24 C25 C34 122.5(3) . . ?
C25 N26 C27 124.0(3) . . ?
C25 N26 H26 112.6(19) . . ?
C27 N26 H26 123.4(19) . . ?
N26 C27 C32 119.0(3) . . ?
N26 C27 C28 120.4(3) . . ?
C32 C27 C28 120.5(3) . . ?
C29 C28 C27 119.1(3) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 C30 121.0(3) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C31 C30 C29 120.3(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 120.4(3) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C27 C32 C31 118.6(3) . . ?
C27 C32 C33 118.0(3) . . ?
C31 C32 C33 123.3(3) . . ?
C34 C33 C32 121.5(3) . . ?
C34 C33 H33 119.2 . . ?
C32 C33 H33 119.2 . . ?
C33 C34 C25 120.0(3) . . ?
C33 C34 C11 122.7(3) . . ?
C25 C34 C11 117.3(2) . . ?
O40 C40 C12 123.6(3) . . ?
O40 C40 C41 115.3(3) . . ?
C12 C40 C41 121.1(3) . . ?
C42 C41 C46 118.9(3) . . ?
C42 C41 C40 121.7(3) . . ?
C46 C41 C40 119.4(3) . . ?
C41 C42 C43 120.4(3) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C44 C43 C42 120.3(4) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C45 120.2(4) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C44 C45 C46 119.9(4) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C41 C46 C45 120.4(3) . . ?
C41 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
O50 C50 C24 123.4(3) . . ?
O50 C50 C51 114.4(3) . . ?
C24 C50 C51 122.1(3) . . ?
C52 C51 C56 118.9(3) . . ?
C52 C51 C50 123.3(3) . . ?
C56 C51 C50 117.8(3) . . ?
C51 C52 C53 120.0(3) . . ?
C51 C52 H52 120.0 . . ?
C53 C52 H52 120.0 . . ?
C54 C53 C52 120.8(4) . . ?
C54 C53 H53 119.6 . . ?
C52 C53 H53 119.6 . . ?
C53 C54 C55 119.5(4) . . ?
C53 C54 H54 120.2 . . ?
C55 C54 H54 120.2 . . ?
C54 C55 C56 119.8(4) . . ?
C54 C55 H55 120.1 . . ?
C56 C55 H55 120.1 . . ?
C51 C56 C55 121.0(4) . . ?
C51 C56 H56 119.5 . . ?
C55 C56 H56 119.5 . . ?
C66 C61 C62 119.0(3) . . ?
C66 C61 N1 123.2(3) . . ?
C62 C61 N1 117.6(2) . . ?
C63 C62 C61 118.9(3) . . ?
C63 C62 C67 120.7(3) . . ?
C61 C62 C67 120.3(3) . . ?
C64 C63 C62 121.5(3) . . ?
C64 C63 H63 119.3 . . ?
C62 C63 H63 119.3 . . ?
C63 C64 C65 119.1(3) . . ?
C63 C64 H64 120.5 . . ?
C65 C64 H64 120.5 . . ?
C64 C65 C66 120.8(3) . . ?
C64 C65 H65 119.6 . . ?
C66 C65 H65 119.6 . . ?
C65 C66 C61 120.7(3) . . ?
C65 C66 H66 119.6 . . ?
C61 C66 H66 119.6 . . ?
C68 C67 C62 179.3(3) . . ?
C67 C68 C71 179.4(3) . . ?
C76 C71 C72 118.6(3) . . ?
C76 C71 C68 120.9(3) . . ?
C72 C71 C68 120.5(3) . . ?
C71 C72 C73 119.9(4) . . ?
C71 C72 H72 120.1 . . ?
C73 C72 H72 120.1 . . ?
C74 C73 C72 120.7(4) . . ?
C74 C73 H73 119.7 . . ?
C72 C73 H73 119.7 . . ?
C73 C74 C75 120.0(4) . . ?
C73 C74 H74 120.0 . . ?
C75 C74 H74 120.0 . . ?
C74 C75 C76 120.1(4) . . ?
C74 C75 H75 119.9 . . ?
C76 C75 H75 119.9 . . ?
C71 C76 C75 120.7(3) . . ?
C71 C76 H76 119.7 . . ?
C75 C76 H76 119.7 . . ?
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
N1 C61 1.419(3) . ?
N1 C11 1.465(3) . ?
N1 C23 1.478(3) . ?
C11 C34 1.508(4) . ?
C11 C12 1.531(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.400(4) . ?
C12 C40 1.402(4) . ?
C13 N14 1.362(3) . ?
C13 C22 1.444(4) . ?
N14 C15 1.373(4) . ?
N14 H14 0.97(3) . ?
C15 C20 1.396(4) . ?
C15 C16 1.398(4) . ?
C16 C17 1.367(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.373(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.408(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.432(4) . ?
C21 C22 1.350(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.520(4) . ?
C23 C24 1.530(4) . ?
C23 H23 1.0000 . ?
C24 C50 1.403(4) . ?
C24 C25 1.418(4) . ?
C25 N26 1.360(3) . ?
C25 C34 1.432(4) . ?
N26 C27 1.380(4) . ?
N26 H26 0.88(3) . ?
C27 C32 1.395(4) . ?
C27 C28 1.400(4) . ?
C28 C29 1.370(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.362(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.407(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.427(4) . ?
C33 C34 1.357(4) . ?
C33 H33 0.9500 . ?
C40 O40 1.274(3) . ?
C40 C41 1.499(4) . ?
C41 C42 1.383(4) . ?
C41 C46 1.386(4) . ?
C42 C43 1.384(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.365(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.375(5) . ?
C44 H44 0.9500 . ?
C45 C46 1.387(5) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C50 O50 1.283(3) . ?
C50 C51 1.504(4) . ?
C51 C52 1.377(4) . ?
C51 C56 1.387(4) . ?
C52 C53 1.398(4) . ?
C52 H52 0.9500 . ?
C53 C54 1.372(5) . ?
C53 H53 0.9500 . ?
C54 C55 1.378(5) . ?
C54 H54 0.9500 . ?
C55 C56 1.388(5) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C61 C66 1.386(4) . ?
C61 C62 1.406(4) . ?
C62 C63 1.397(4) . ?
C62 C67 1.430(4) . ?
C63 C64 1.377(4) . ?
C63 H63 0.9500 . ?
C64 C65 1.377(4) . ?
C64 H64 0.9500 . ?
C65 C66 1.383(4) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C67 C68 1.192(4) . ?
C68 C71 1.439(5) . ?
C71 C76 1.377(4) . ?
C71 C72 1.384(5) . ?
C72 C73 1.390(5) . ?
C72 H72 0.9500 . ?
C73 C74 1.358(6) . ?
C73 H73 0.9500 . ?
C74 C75 1.361(5) . ?
C74 H74 0.9500 . ?
C75 C76 1.386(5) . ?
C75 H75 0.9500 . ?
C76 H76 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C61 N1 C11 C34 150.6(2) . . . . ?
C23 N1 C11 C34 -68.8(3) . . . . ?
C61 N1 C11 C12 -86.7(3) . . . . ?
C23 N1 C11 C12 54.0(3) . . . . ?
N1 C11 C12 C13 -23.8(3) . . . . ?
C34 C11 C12 C13 95.8(3) . . . . ?
N1 C11 C12 C40 158.7(2) . . . . ?
C34 C11 C12 C40 -81.7(3) . . . . ?
C40 C12 C13 N14 -4.0(4) . . . . ?
C11 C12 C13 N14 178.5(2) . . . . ?
C40 C12 C13 C22 178.5(3) . . . . ?
C11 C12 C13 C22 1.0(4) . . . . ?
C12 C13 N14 C15 -177.0(3) . . . . ?
C22 C13 N14 C15 0.7(4) . . . . ?
C13 N14 C15 C20 1.3(4) . . . . ?
C13 N14 C15 C16 -179.0(3) . . . . ?
N14 C15 C16 C17 179.1(3) . . . . ?
C20 C15 C16 C17 -1.2(5) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C16 C17 C18 C19 0.2(6) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
N14 C15 C20 C19 -179.0(3) . . . . ?
C16 C15 C20 C19 1.3(4) . . . . ?
N14 C15 C20 C21 -0.6(4) . . . . ?
C16 C15 C20 C21 179.7(3) . . . . ?
C18 C19 C20 C15 -0.7(5) . . . . ?
C18 C19 C20 C21 -179.0(3) . . . . ?
C15 C20 C21 C22 -2.3(4) . . . . ?
C19 C20 C21 C22 176.0(3) . . . . ?
C20 C21 C22 C13 4.4(4) . . . . ?
C20 C21 C22 C23 -173.1(2) . . . . ?
N14 C13 C22 C21 -3.6(4) . . . . ?
C12 C13 C22 C21 174.0(3) . . . . ?
N14 C13 C22 C23 174.1(2) . . . . ?
C12 C13 C22 C23 -8.3(4) . . . . ?
C61 N1 C23 C22 81.0(3) . . . . ?
C11 N1 C23 C22 -60.1(3) . . . . ?
C61 N1 C23 C24 -156.6(2) . . . . ?
C11 N1 C23 C24 62.4(3) . . . . ?
C21 C22 C23 N1 -145.0(3) . . . . ?
C13 C22 C23 N1 37.4(3) . . . . ?
C21 C22 C23 C24 94.0(3) . . . . ?
C13 C22 C23 C24 -83.7(3) . . . . ?
N1 C23 C24 C50 160.6(2) . . . . ?
C22 C23 C24 C50 -77.6(3) . . . . ?
N1 C23 C24 C25 -24.3(3) . . . . ?
C22 C23 C24 C25 97.4(3) . . . . ?
C50 C24 C25 N26 -7.4(4) . . . . ?
C23 C24 C25 N26 177.4(2) . . . . ?
C50 C24 C25 C34 171.7(3) . . . . ?
C23 C24 C25 C34 -3.5(4) . . . . ?
C24 C25 N26 C27 178.4(3) . . . . ?
C34 C25 N26 C27 -0.8(4) . . . . ?
C25 N26 C27 C32 2.8(4) . . . . ?
C25 N26 C27 C28 -177.8(3) . . . . ?
N26 C27 C28 C29 -179.9(3) . . . . ?
C32 C27 C28 C29 -0.5(4) . . . . ?
C27 C28 C29 C30 0.5(5) . . . . ?
C28 C29 C30 C31 0.1(5) . . . . ?
C29 C30 C31 C32 -0.6(5) . . . . ?
N26 C27 C32 C31 179.4(3) . . . . ?
C28 C27 C32 C31 0.0(4) . . . . ?
N26 C27 C32 C33 -1.3(4) . . . . ?
C28 C27 C32 C33 179.2(3) . . . . ?
C30 C31 C32 C27 0.6(4) . . . . ?
C30 C31 C32 C33 -178.6(3) . . . . ?
C27 C32 C33 C34 -2.1(4) . . . . ?
C31 C32 C33 C34 177.1(3) . . . . ?
C32 C33 C34 C25 4.1(4) . . . . ?
C32 C33 C34 C11 -173.7(2) . . . . ?
N26 C25 C34 C33 -2.7(4) . . . . ?
C24 C25 C34 C33 178.2(3) . . . . ?
N26 C25 C34 C11 175.2(2) . . . . ?
C24 C25 C34 C11 -3.9(4) . . . . ?
N1 C11 C34 C33 -144.0(3) . . . . ?
C12 C11 C34 C33 91.8(3) . . . . ?
N1 C11 C34 C25 38.1(3) . . . . ?
C12 C11 C34 C25 -86.1(3) . . . . ?
C13 C12 C40 O40 -2.0(4) . . . . ?
C11 C12 C40 O40 175.4(3) . . . . ?
C13 C12 C40 C41 179.6(3) . . . . ?
C11 C12 C40 C41 -3.0(4) . . . . ?
O40 C40 C41 C42 116.6(3) . . . . ?
C12 C40 C41 C42 -64.9(4) . . . . ?
O40 C40 C41 C46 -62.1(4) . . . . ?
C12 C40 C41 C46 116.4(3) . . . . ?
C46 C41 C42 C43 -0.4(5) . . . . ?
C40 C41 C42 C43 -179.1(3) . . . . ?
C41 C42 C43 C44 -0.5(5) . . . . ?
C42 C43 C44 C45 1.0(6) . . . . ?
C43 C44 C45 C46 -0.6(7) . . . . ?
C42 C41 C46 C45 0.8(5) . . . . ?
C40 C41 C46 C45 179.6(3) . . . . ?
C44 C45 C46 C41 -0.3(6) . . . . ?
C25 C24 C50 O50 5.3(4) . . . . ?
C23 C24 C50 O50 -179.8(3) . . . . ?
C25 C24 C50 C51 -170.8(3) . . . . ?
C23 C24 C50 C51 4.0(4) . . . . ?
O50 C50 C51 C52 115.9(3) . . . . ?
C24 C50 C51 C52 -67.6(4) . . . . ?
O50 C50 C51 C56 -63.1(4) . . . . ?
C24 C50 C51 C56 113.4(3) . . . . ?
C56 C51 C52 C53 -0.4(5) . . . . ?
C50 C51 C52 C53 -179.4(3) . . . . ?
C51 C52 C53 C54 -0.4(5) . . . . ?
C52 C53 C54 C55 0.7(6) . . . . ?
C53 C54 C55 C56 -0.3(6) . . . . ?
C52 C51 C56 C55 0.8(5) . . . . ?
C50 C51 C56 C55 179.9(3) . . . . ?
C54 C55 C56 C51 -0.5(5) . . . . ?
C11 N1 C61 C66 26.2(4) . . . . ?
C23 N1 C61 C66 -111.8(3) . . . . ?
C11 N1 C61 C62 -148.5(2) . . . . ?
C23 N1 C61 C62 73.5(3) . . . . ?
C66 C61 C62 C63 1.8(4) . . . . ?
N1 C61 C62 C63 176.7(2) . . . . ?
C66 C61 C62 C67 -174.2(3) . . . . ?
N1 C61 C62 C67 0.8(4) . . . . ?
C61 C62 C63 C64 -1.9(4) . . . . ?
C67 C62 C63 C64 174.0(3) . . . . ?
C62 C63 C64 C65 0.3(5) . . . . ?
C63 C64 C65 C66 1.4(5) . . . . ?
C64 C65 C66 C61 -1.5(4) . . . . ?
C62 C61 C66 C65 -0.1(4) . . . . ?
N1 C61 C66 C65 -174.8(3) . . . . ?
C76 C71 C72 C73 3.1(6) . . . . ?
C68 C71 C72 C73 -178.1(4) . . . . ?
C71 C72 C73 C74 -2.0(7) . . . . ?
C72 C73 C74 C75 0.8(8) . . . . ?
C73 C74 C75 C76 -0.6(7) . . . . ?
C72 C71 C76 C75 -3.1(5) . . . . ?
C68 C71 C76 C75 178.2(3) . . . . ?
C74 C75 C76 C71 1.8(6) . . . . ?
