#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:01:18 +0300 (Fri, 05 May 2023) $
#$Revision: 283403 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/22/7062283.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_7062283
loop_
_publ_author_name
'Sun, Jing'
'Yan, Chen'
'Sun, Qiu'
'Han, Ying'
'Yan, Chao-Guo'
_publ_section_title
;
 Selective construction of polycyclic cyclohepta[b]indoles and
 cyclopenta[b]indoles via cycloaddition reaction of
 3-(indol-3-yl)maleimides and (indol-2-yl)methanols
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6694
_journal_page_last               6699
_journal_paper_doi               10.1039/D3NJ00013C
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C37 H27 F N4 O3'
_chemical_formula_sum            'C37 H27 F N4 O3'
_chemical_formula_weight         594.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-06-08 deposited with the CCDC.	2023-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.155(3)
_cell_length_b                   9.1523(9)
_cell_length_c                   25.150(3)
_cell_measurement_reflns_used    6274
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.96
_cell_measurement_theta_min      2.33
_cell_volume                     6941.1(13)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1808
_diffrn_reflns_av_unetI/netI     0.1644
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            67793
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.326
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_description       block
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 1816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.6(7)
_refine_ls_extinction_coef       0.0018(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     816
_refine_ls_number_reflns         12103
_refine_ls_number_restraints     213
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.2335
_refine_ls_R_factor_gt           0.1035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1766P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2609
_refine_ls_wR_factor_ref         0.3010
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                5457
_reflns_number_total             12103
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00013c2.cif
_cod_data_source_block           5j
_cod_depositor_comments
'Adding full bibliography for 7062276--7062283.cif.'
_cod_original_cell_volume        6941.2(12)
_cod_database_code               7062283
_shelx_shelxl_version_number     2014/7
_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   0.982
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -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
C1 C 0.5208(5) -0.092(3) 0.3142(7) 0.157(6) Uani 1 1 d . U . . .
H1A H 0.5161 -0.1899 0.3021 0.235 Uiso 1 1 calc R U . . .
H1B H 0.5123 -0.0243 0.2868 0.235 Uiso 1 1 calc R U . . .
H1C H 0.5031 -0.0743 0.3454 0.235 Uiso 1 1 calc R U . . .
C2 C 0.6034(3) -0.096(2) 0.2929(4) 0.111(3) Uani 1 1 d D U . . .
C3 C 0.6034(4) -0.121(2) 0.2382(4) 0.115(3) Uani 1 1 d D U . . .
H3 H 0.5770 -0.1412 0.2205 0.138 Uiso 1 1 calc R U . . .
C4 C 0.6429(4) -0.117(2) 0.2109(4) 0.113(3) Uani 1 1 d D U . . .
H4 H 0.6439 -0.1447 0.1753 0.136 Uiso 1 1 calc R U . . .
C5 C 0.6814(4) -0.072(2) 0.2364(4) 0.110(3) Uani 1 1 d D U . . .
H5 H 0.7079 -0.0679 0.2177 0.132 Uiso 1 1 calc R U . . .
C6 C 0.6805(3) -0.031(2) 0.2895(4) 0.102(3) Uani 1 1 d D U . . .
H6 H 0.7059 0.0042 0.3059 0.122 Uiso 1 1 calc R U . . .
C7 C 0.6412(3) -0.045(2) 0.3179(4) 0.097(3) Uani 1 1 d D U . . .
C8 C 0.6277(4) -0.003(2) 0.3718(5) 0.093(3) Uani 1 1 d . U . . .
C9 C 0.5849(4) -0.028(2) 0.3751(5) 0.106(3) Uani 1 1 d . U . . .
H9 H 0.5684 -0.0185 0.4061 0.127 Uiso 1 1 calc R U . . .
C10 C 0.6300(4) 0.0909(14) 0.4628(5) 0.064(3) Uani 1 1 d . . . . .
C11 C 0.6573(4) 0.0623(12) 0.4141(4) 0.049(3) Uani 1 1 d . . . . .
C12 C 0.6949(3) -0.0424(11) 0.4357(4) 0.045(3) Uani 1 1 d . . . . .
H12 H 0.6986 -0.1265 0.4120 0.054 Uiso 1 1 calc R U . . .
C13 C 0.6792(4) -0.0901(13) 0.4881(5) 0.059(3) Uani 1 1 d . . . . .
C14 C 0.6220(4) -0.0015(14) 0.5572(5) 0.074(4) Uani 1 1 d . . . . .
H14A H 0.6228 -0.0978 0.5722 0.110 Uiso 1 1 calc R U . . .
H14B H 0.5918 0.0303 0.5541 0.110 Uiso 1 1 calc R U . . .
H14C H 0.6380 0.0647 0.5798 0.110 Uiso 1 1 calc R U . . .
C15 C 0.7129(6) 0.3969(14) 0.3662(5) 0.066(4) Uani 1 1 d . . . . .
C16 C 0.7185(8) 0.5315(16) 0.3445(6) 0.098(6) Uani 1 1 d . . . . .
H16 H 0.6951 0.5841 0.3298 0.117 Uiso 1 1 calc R U . . .
C17 C 0.7602(12) 0.5835(18) 0.3457(6) 0.128(10) Uani 1 1 d . . . . .
H17 H 0.7649 0.6754 0.3310 0.154 Uiso 1 1 calc R U . . .
C18 C 0.7972(7) 0.512(2) 0.3669(7) 0.106(6) Uani 1 1 d . . . . .
H18 H 0.8248 0.5577 0.3669 0.127 Uiso 1 1 calc R U . . .
C19 C 0.7923(5) 0.3756(15) 0.3876(5) 0.076(4) Uani 1 1 d . . . . .
H19 H 0.8161 0.3206 0.4000 0.091 Uiso 1 1 calc R U . . .
C20 C 0.7451(6) 0.3208(12) 0.3888(5) 0.077(4) Uani 1 1 d . . . . .
C21 C 0.7274(4) 0.1836(12) 0.4098(5) 0.057(3) Uani 1 1 d . . . . .
C22 C 0.6827(4) 0.1922(14) 0.3966(4) 0.059(3) Uani 1 1 d . . . . .
C23 C 0.8908(3) 0.0616(13) 0.4046(4) 0.077(4) Uani 1 1 d D . . . .
H23 H 0.8676 0.0694 0.3802 0.092 Uiso 1 1 calc R U . . .
C24 C 0.9257(4) 0.1603(12) 0.4017(5) 0.070(4) Uani 1 1 d D . . . .
H24 H 0.9253 0.2353 0.3768 0.084 Uiso 1 1 calc R U . . .
C25 C 0.9610(4) 0.1455(16) 0.4365(6) 0.102(6) Uani 1 1 d D . . . .
H25 H 0.9850 0.2093 0.4349 0.122 Uiso 1 1 calc R U . . .
C26 C 0.9600(4) 0.0341(17) 0.4737(6) 0.099(5) Uani 1 1 d D . . . .
H26 H 0.9833 0.0252 0.4977 0.119 Uiso 1 1 calc R U . . .
C27 C 0.9254(4) -0.0643(15) 0.4761(5) 0.088(5) Uani 1 1 d D . . . .
H27 H 0.9262 -0.1412 0.5002 0.106 Uiso 1 1 calc R U . . .
C28 C 0.8892(3) -0.0479(12) 0.4423(5) 0.067(4) Uani 1 1 d D . . . .
C29 C 0.8478(4) -0.1489(14) 0.4445(6) 0.072(4) Uani 1 1 d . . . . .
H29A H 0.8459 -0.2042 0.4117 0.086 Uiso 1 1 calc R U . . .
H29B H 0.8513 -0.2179 0.4735 0.086 Uiso 1 1 calc R U . . .
C30 C 0.7779(4) -0.0394(12) 0.4140(6) 0.057(3) Uani 1 1 d . . . . .
C31 C 0.7394(3) 0.0451(11) 0.4404(4) 0.046(3) Uani 1 1 d . . . . .
C32 C 0.7567(4) 0.0725(13) 0.4962(5) 0.054(2) Uani 1 1 d . U . . .
C33 C 0.7395(4) 0.1558(13) 0.5367(5) 0.063(2) Uani 1 1 d . U . . .
H33 H 0.7127 0.2051 0.5335 0.076 Uiso 1 1 calc R U . . .
C34 C 0.7657(4) 0.1615(15) 0.5846(5) 0.075(3) Uani 1 1 d . U . . .
C35 C 0.8036(5) 0.0848(14) 0.5887(6) 0.077(4) Uani 1 1 d . U . . .
H35 H 0.8188 0.0874 0.6209 0.092 Uiso 1 1 calc R U . . .
C36 C 0.8213(4) 0.0019(13) 0.5475(5) 0.062(3) Uani 1 1 d . U . . .
H36 H 0.8481 -0.0480 0.5506 0.074 Uiso 1 1 calc R U . . .
C37 C 0.7966(4) -0.0003(13) 0.5025(5) 0.055(2) Uani 1 1 d . U . . .
C38 C 0.7865(5) 0.804(2) 0.1817(7) 0.129(7) Uani 1 1 d . . . . .
H38A H 0.7861 0.8920 0.1608 0.194 Uiso 1 1 calc R U . . .
H38B H 0.7827 0.8287 0.2186 0.194 Uiso 1 1 calc R U . . .
H38C H 0.7629 0.7411 0.1706 0.194 Uiso 1 1 calc R U . . .
C39 C 0.8656(3) 0.7216(13) 0.2121(4) 0.065(3) Uani 1 1 d D . . . .
C40 C 0.8698(4) 0.7894(13) 0.2609(4) 0.075(4) Uani 1 1 d D . . . .
H40 H 0.8470 0.8461 0.2747 0.090 Uiso 1 1 calc R U . . .
C41 C 0.9091(4) 0.7709(14) 0.2888(4) 0.081(4) Uani 1 1 d D . . . .
H41 H 0.9124 0.8131 0.3222 0.097 Uiso 1 1 calc R U . . .
C42 C 0.9434(4) 0.6902(15) 0.2672(4) 0.084(4) Uani 1 1 d D . . . .
H42 H 0.9696 0.6790 0.2862 0.101 Uiso 1 1 calc R U . . .
C43 C 0.9392(3) 0.6257(13) 0.2175(4) 0.068(4) Uani 1 1 d D . . . .
H43 H 0.9622 0.5696 0.2036 0.082 Uiso 1 1 calc R U . . .
C44 C 0.9002(3) 0.6460(11) 0.1889(3) 0.054(3) Uani 1 1 d D . . . .
C45 C 0.8846(3) 0.6001(12) 0.1370(4) 0.048(3) Uani 1 1 d . . . . .
C46 C 0.8424(4) 0.6508(13) 0.1321(5) 0.067(3) Uani 1 1 d . . . . .
H46 H 0.8243 0.6339 0.1028 0.080 Uiso 1 1 calc R U . . .
C47 C 0.8809(4) 0.4827(12) 0.0478(4) 0.045(3) Uani 1 1 d . . . . .
C48 C 0.9105(3) 0.5150(11) 0.0964(4) 0.040(3) Uani 1 1 d . . . . .
C49 C 0.9503(3) 0.6028(11) 0.0688(4) 0.046(3) Uani 1 1 d . . . . .
H49 H 0.9573 0.6906 0.0895 0.055 Uiso 1 1 calc R U . . .
C50 C 0.9321(4) 0.6437(13) 0.0174(5) 0.055(3) Uani 1 1 d . . . . .
C51 C 0.8731(5) 0.5578(17) -0.0439(5) 0.086(4) Uani 1 1 d . . . . .
H51A H 0.8835 0.4747 -0.0636 0.130 Uiso 1 1 calc R U . . .
H51B H 0.8798 0.6456 -0.0633 0.130 Uiso 1 1 calc R U . . .
H51C H 0.8416 0.5503 -0.0389 0.130 Uiso 1 1 calc R U . . .
C52 C 0.9569(4) 0.1621(11) 0.1438(4) 0.055(3) Uani 1 1 d . . . . .
C53 C 0.9578(4) 0.0239(13) 0.1657(5) 0.068(4) Uani 1 1 d . . . . .
H53 H 0.9336 -0.0154 0.1836 0.081 Uiso 1 1 calc R U . . .
C54 C 0.9987(6) -0.0555(16) 0.1593(6) 0.087(5) Uani 1 1 d . . . . .
H54 H 1.0017 -0.1492 0.1731 0.105 Uiso 1 1 calc R U . . .
C55 C 1.0338(5) 0.0099(16) 0.1321(6) 0.073(4) Uani 1 1 d . . . . .
H55 H 1.0596 -0.0440 0.1272 0.088 Uiso 1 1 calc R U . . .
C56 C 1.0323(4) 0.1542(12) 0.1113(4) 0.056(3) Uani 1 1 d . . . . .
H56 H 1.0569 0.1967 0.0953 0.067 Uiso 1 1 calc R U . . .
C57 C 0.9932(4) 0.2276(11) 0.1161(4) 0.048(3) Uani 1 1 d . . . . .
C58 C 0.9759(4) 0.3643(12) 0.0991(4) 0.050(3) Uani 1 1 d . . . . .
C59 C 0.9336(4) 0.3793(11) 0.1139(4) 0.046(3) Uani 1 1 d . . . . .
C60 C 1.1460(4) 0.4482(14) 0.0949(6) 0.073(4) Uani 1 1 d . . . . .
H60 H 1.1216 0.4341 0.1169 0.088 Uiso 1 1 calc R U . . .
C61 C 1.1836(6) 0.354(2) 0.0992(7) 0.107(5) Uani 1 1 d . . . . .
H61 H 1.1859 0.2841 0.1258 0.128 Uiso 1 1 calc R U . . .
C62 C 1.2146(6) 0.3729(14) 0.0633(8) 0.089(5) Uani 1 1 d . . . . .
H62 H 1.2396 0.3135 0.0655 0.107 Uiso 1 1 calc R U . . .
C63 C 1.2133(4) 0.4690(17) 0.0242(6) 0.076(4) Uani 1 1 d . . . . .
H63 H 1.2347 0.4700 -0.0025 0.091 Uiso 1 1 calc R U . . .
C64 C 1.1793(4) 0.5669(16) 0.0247(6) 0.077(4) Uani 1 1 d . . . . .
H64 H 1.1792 0.6431 0.0003 0.092 Uiso 1 1 calc R U . . .
C65 C 1.1459(4) 0.5559(13) 0.0594(5) 0.066(4) Uani 1 1 d . . . . .
C66 C 1.1060(3) 0.6621(12) 0.0569(5) 0.057(3) Uani 1 1 d . . . . .
H66A H 1.1048 0.7186 0.0895 0.068 Uiso 1 1 calc R U . . .
H66B H 1.1102 0.7297 0.0276 0.068 Uiso 1 1 calc R U . . .
C67 C 1.0331(3) 0.5792(11) 0.0897(5) 0.044(3) Uani 1 1 d . . . . .
C68 C 0.9917(3) 0.4969(11) 0.0677(4) 0.037(2) Uani 1 1 d . . . . .
C69 C 1.0088(4) 0.4574(12) 0.0110(5) 0.0550(14) Uani 1 1 d . U . . .
C70 C 0.9893(4) 0.3740(12) -0.0284(4) 0.0557(14) Uani 1 1 d . U . . .
H70 H 0.9613 0.3338 -0.0234 0.067 Uiso 1 1 calc R U . . .
C71 C 1.0117(4) 0.3513(13) -0.0748(5) 0.0563(14) Uani 1 1 d . U . . .
C72 C 1.0552(4) 0.4129(12) -0.0831(5) 0.0567(14) Uani 1 1 d . U . . .
H72 H 1.0698 0.3974 -0.1151 0.068 Uiso 1 1 calc R U . . .
C73 C 1.0754(4) 0.4955(13) -0.0434(4) 0.0563(14) Uani 1 1 d . U . . .
H73 H 1.1034 0.5362 -0.0480 0.068 Uiso 1 1 calc R U . . .
C74 C 1.0504(4) 0.5144(12) 0.0053(5) 0.0553(14) Uani 1 1 d . U . . .
F1 F 0.7485(3) 0.2394(11) 0.6251(3) 0.120(3) Uani 1 1 d . . . . .
F2 F 0.9940(3) 0.2776(10) -0.1151(3) 0.100(3) Uani 1 1 d . . . . .
N1 N 0.5677(4) -0.0711(18) 0.3271(4) 0.118(3) Uani 1 1 d . U . . .
N2 N 0.6430(3) -0.0037(10) 0.5034(3) 0.052(2) Uani 1 1 d . . . . .
N3 N 0.6749(4) 0.3149(10) 0.3711(4) 0.064(3) Uani 1 1 d . . . . .
H3A H 0.6494 0.3406 0.3590 0.077 Uiso 1 1 calc R U . . .
N4 N 0.8086(3) -0.0710(10) 0.4517(4) 0.052(2) Uani 1 1 d . . . . .
N5 N 0.8305(3) 0.7272(13) 0.1743(4) 0.077(3) Uani 1 1 d . . . . .
N6 N 0.8946(3) 0.5620(10) 0.0069(4) 0.053(2) Uani 1 1 d . . . . .
N7 N 0.9205(3) 0.2568(11) 0.1424(4) 0.065(3) Uani 1 1 d . . . . .
H7 H 0.8949 0.2419 0.1566 0.078 Uiso 1 1 calc R U . . .
N8 N 1.0640(3) 0.5849(9) 0.0498(4) 0.052(2) Uani 1 1 d . . . . .
O1 O 0.6018(3) 0.1837(11) 0.4675(3) 0.080(3) Uani 1 1 d . . . . .
O2 O 0.6943(3) -0.1863(9) 0.5177(3) 0.070(2) Uani 1 1 d . . . . .
O3 O 0.7809(3) -0.0728(9) 0.3672(4) 0.071(2) Uani 1 1 d . . . . .
O4 O 0.8492(3) 0.3992(9) 0.0468(3) 0.067(2) Uani 1 1 d . . . . .
O5 O 0.9490(3) 0.7412(10) -0.0128(4) 0.077(3) Uani 1 1 d . . . . .
O6 O 1.0368(2) 0.6211(9) 0.1344(3) 0.063(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
F F 0.0171 0.0103 '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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 120.5(8) . . ?
C7 C2 N1 107.5(9) . . ?
C3 C2 N1 129.3(10) . . ?
C4 C3 C2 119.1(8) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.0(8) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.7(7) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.2(7) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 119.9(7) . . ?
C2 C7 C8 106.2(8) . . ?
C6 C7 C8 133.7(9) . . ?
C9 C8 C7 106.8(11) . . ?
C9 C8 C11 127.1(12) . . ?
C7 C8 C11 126.1(10) . . ?
C8 C9 N1 111.4(12) . . ?
C8 C9 H9 124.3 . . ?
N1 C9 H9 124.3 . . ?
O1 C10 N2 124.2(12) . . ?
O1 C10 C11 126.1(11) . . ?
N2 C10 C11 109.6(10) . . ?
C22 C11 C10 112.7(9) . . ?
C22 C11 C8 114.6(10) . . ?
C10 C11 C8 108.7(9) . . ?
C22 C11 C12 102.5(9) . . ?
C10 C11 C12 102.7(9) . . ?
C8 C11 C12 115.1(10) . . ?
C13 C12 C31 111.1(9) . . ?
C13 C12 C11 104.9(9) . . ?
C31 C12 C11 109.3(8) . . ?
C13 C12 H12 110.5 . . ?
C31 C12 H12 110.5 . . ?
C11 C12 H12 110.5 . . ?
O2 C13 N2 121.5(11) . . ?
O2 C13 C12 129.1(11) . . ?
N2 C13 C12 109.3(11) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 124.0(17) . . ?
C20 C15 N3 106.7(12) . . ?
C16 C15 N3 129.4(16) . . ?
C17 C16 C15 115.3(19) . . ?
C17 C16 H16 122.3 . . ?
C15 C16 H16 122.3 . . ?
C16 C17 C18 126.2(16) . . ?
C16 C17 H17 116.9 . . ?
C18 C17 H17 116.9 . . ?
C19 C18 C17 119.2(16) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 114.5(15) . . ?
C18 C19 H19 122.7 . . ?
C20 C19 H19 122.7 . . ?
C15 C20 C21 109.7(14) . . ?
C15 C20 C19 120.6(13) . . ?
C21 C20 C19 129.6(14) . . ?
C22 C21 C20 102.7(11) . . ?
C22 C21 C31 113.4(10) . . ?
C20 C21 C31 143.8(12) . . ?
N3 C22 C21 109.7(11) . . ?
N3 C22 C11 137.6(12) . . ?
C21 C22 C11 112.7(10) . . ?
C28 C23 C24 122.2(8) . . ?
C28 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
C25 C24 C23 119.1(7) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 118.8(8) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C27 C26 C25 121.8(8) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C26 C27 C28 119.8(8) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C23 C28 C27 118.2(7) . . ?
C23 C28 C29 118.9(10) . . ?
C27 C28 C29 122.9(10) . . ?
N4 C29 C28 112.4(10) . . ?
N4 C29 H29A 109.1 . . ?
C28 C29 H29A 109.1 . . ?
N4 C29 H29B 109.1 . . ?
C28 C29 H29B 109.1 . . ?
H29A C29 H29B 107.8 . . ?
O3 C30 N4 124.8(11) . . ?
O3 C30 C31 126.6(11) . . ?
N4 C30 C31 108.6(11) . . ?
C32 C31 C21 114.2(9) . . ?
C32 C31 C30 102.8(9) . . ?
C21 C31 C30 112.1(9) . . ?
C32 C31 C12 116.7(9) . . ?
C21 C31 C12 100.5(8) . . ?
C30 C31 C12 110.8(8) . . ?
C33 C32 C37 120.7(11) . . ?
C33 C32 C31 130.3(10) . . ?
C37 C32 C31 109.0(10) . . ?
C32 C33 C34 115.6(11) . . ?
C32 C33 H33 122.2 . . ?
C34 C33 H33 122.2 . . ?
C35 C34 F1 123.0(12) . . ?
C35 C34 C33 120.8(13) . . ?
F1 C34 C33 116.1(12) . . ?
C34 C35 C36 123.6(13) . . ?
C34 C35 H35 118.2 . . ?
C36 C35 H35 118.2 . . ?
C37 C36 C35 114.8(12) . . ?
C37 C36 H36 122.6 . . ?
C35 C36 H36 122.6 . . ?
C36 C37 C32 124.5(12) . . ?
C36 C37 N4 126.4(11) . . ?
C32 C37 N4 109.0(10) . . ?
N5 C38 H38A 109.5 . . ?
N5 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N5 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C44 121.9(7) . . ?
C40 C39 N5 130.3(8) . . ?
C44 C39 N5 107.3(8) . . ?
C39 C40 C41 118.3(7) . . ?
C39 C40 H40 120.8 . . ?
C41 C40 H40 120.8 . . ?
C42 C41 C40 120.3(7) . . ?
C42 C41 H41 119.8 . . ?
C40 C41 H41 119.8 . . ?
C41 C42 C43 121.0(7) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C42 C43 C44 119.0(7) . . ?
C42 C43 H43 120.5 . . ?
C44 C43 H43 120.5 . . ?
C39 C44 C43 119.2(7) . . ?
C39 C44 C45 106.2(7) . . ?
C43 C44 C45 134.5(8) . . ?
C46 C45 C44 106.6(9) . . ?
C46 C45 C48 126.9(10) . . ?
C44 C45 C48 126.4(9) . . ?
N5 C46 C45 111.2(11) . . ?
N5 C46 H46 124.4 . . ?
C45 C46 H46 124.4 . . ?
O4 C47 N6 124.7(11) . . ?
O4 C47 C48 126.0(10) . . ?
N6 C47 C48 109.3(10) . . ?
C59 C48 C45 118.3(9) . . ?
C59 C48 C47 110.2(8) . . ?
C45 C48 C47 109.8(8) . . ?
C59 C48 C49 101.2(8) . . ?
C45 C48 C49 115.0(8) . . ?
C47 C48 C49 100.7(8) . . ?
C50 C49 C68 116.2(8) . . ?
C50 C49 C48 103.3(9) . . ?
C68 C49 C48 106.9(8) . . ?
C50 C49 H49 110.0 . . ?
C68 C49 H49 110.0 . . ?
C48 C49 H49 110.0 . . ?
O5 C50 N6 126.3(11) . . ?
O5 C50 C49 123.8(12) . . ?
N6 C50 C49 109.9(10) . . ?
N6 C51 H51A 109.5 . . ?
N6 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N6 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C53 C52 N7 126.3(12) . . ?
C53 C52 C57 124.3(11) . . ?
N7 C52 C57 109.3(9) . . ?
C52 C53 C54 115.7(12) . . ?
C52 C53 H53 122.1 . . ?
C54 C53 H53 122.1 . . ?
C55 C54 C53 119.2(13) . . ?
C55 C54 H54 120.4 . . ?
C53 C54 H54 120.4 . . ?
C54 C55 C56 123.7(12) . . ?
C54 C55 H55 118.2 . . ?
C56 C55 H55 118.2 . . ?
C57 C56 C55 117.0(11) . . ?
C57 C56 H56 121.5 . . ?
C55 C56 H56 121.5 . . ?
C56 C57 C58 136.5(11) . . ?
C56 C57 C52 119.9(10) . . ?
C58 C57 C52 103.5(10) . . ?
C59 C58 C57 110.9(10) . . ?
C59 C58 C68 111.1(9) . . ?
C57 C58 C68 137.9(10) . . ?
C58 C59 N7 109.4(10) . . ?
C58 C59 C48 116.7(9) . . ?
N7 C59 C48 133.8(10) . . ?
C65 C60 C61 120.0(13) . . ?
C65 C60 H60 120.0 . . ?
C61 C60 H60 120.0 . . ?
C62 C61 C60 115.9(15) . . ?
C62 C61 H61 122.1 . . ?
C60 C61 H61 122.1 . . ?
C61 C62 C63 125.3(15) . . ?
C61 C62 H62 117.3 . . ?
C63 C62 H62 117.3 . . ?
C62 C63 C64 117.0(13) . . ?
C62 C63 H63 121.5 . . ?
C64 C63 H63 121.5 . . ?
C65 C64 C63 121.6(13) . . ?
C65 C64 H64 119.2 . . ?
C63 C64 H64 119.2 . . ?
C60 C65 C64 119.5(13) . . ?
C60 C65 C66 119.7(12) . . ?
C64 C65 C66 120.8(11) . . ?
N8 C66 C65 112.0(9) . . ?
N8 C66 H66A 109.2 . . ?
C65 C66 H66A 109.2 . . ?
N8 C66 H66B 109.2 . . ?
C65 C66 H66B 109.2 . . ?
H66A C66 H66B 107.9 . . ?
O6 C67 N8 127.9(10) . . ?
O6 C67 C68 124.4(9) . . ?
N8 C67 C68 107.6(9) . . ?
C58 C68 C67 116.8(8) . . ?
C58 C68 C69 113.1(8) . . ?
C67 C68 C69 99.8(8) . . ?
C58 C68 C49 103.5(8) . . ?
C67 C68 C49 109.2(8) . . ?
C69 C68 C49 114.8(8) . . ?
C74 C69 C70 121.8(11) . . ?
C74 C69 C68 108.1(10) . . ?
C70 C69 C68 130.0(10) . . ?
C71 C70 C69 119.2(11) . . ?
C71 C70 H70 120.4 . . ?
C69 C70 H70 120.4 . . ?
F2 C71 C70 122.1(10) . . ?
F2 C71 C72 116.9(10) . . ?
C70 C71 C72 120.9(11) . . ?
C73 C72 C71 120.4(11) . . ?
C73 C72 H72 119.8 . . ?
C71 C72 H72 119.8 . . ?
C72 C73 C74 116.4(11) . . ?
C72 C73 H73 121.8 . . ?
C74 C73 H73 121.8 . . ?
N8 C74 C69 112.0(10) . . ?
N8 C74 C73 126.8(11) . . ?
C69 C74 C73 121.3(11) . . ?
C9 N1 C2 107.3(10) . . ?
C9 N1 C1 126.7(13) . . ?
C2 N1 C1 126.0(12) . . ?
C10 N2 C13 111.5(10) . . ?
C10 N2 C14 122.4(10) . . ?
C13 N2 C14 125.9(10) . . ?
C22 N3 C15 111.2(11) . . ?
C22 N3 H3A 124.4 . . ?
C15 N3 H3A 124.4 . . ?
C30 N4 C29 126.7(11) . . ?
C30 N4 C37 110.1(9) . . ?
C29 N4 C37 123.0(10) . . ?
C46 N5 C39 108.4(9) . . ?
C46 N5 C38 125.7(11) . . ?
C39 N5 C38 125.8(10) . . ?
C47 N6 C50 113.8(10) . . ?
C47 N6 C51 122.4(10) . . ?
C50 N6 C51 123.8(11) . . ?
C59 N7 C52 106.8(10) . . ?
C59 N7 H7 126.6 . . ?
C52 N7 H7 126.6 . . ?
C74 N8 C67 112.4(9) . . ?
C74 N8 C66 126.5(10) . . ?
C67 N8 C66 121.1(9) . . ?
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 N1 1.464(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.381(6) . ?
C2 C3 1.395(6) . ?
C2 N1 1.397(15) . ?
C3 C4 1.379(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.465(15) . ?
C8 C9 1.311(16) . ?
C8 C11 1.514(16) . ?
C9 N1 1.371(17) . ?
C9 H9 0.9300 . ?
C10 O1 1.208(14) . ?
C10 N2 1.396(14) . ?
C10 C11 1.499(17) . ?
C11 C22 1.482(16) . ?
C11 C12 1.581(15) . ?
C12 C13 1.467(16) . ?
C12 C31 1.567(14) . ?
C12 H12 0.9800 . ?
C13 O2 1.240(14) . ?
C13 N2 1.402(14) . ?
C14 N2 1.493(13) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.324(18) . ?
C15 C16 1.359(19) . ?
C15 N3 1.374(16) . ?
C16 C17 1.35(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.40(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.36(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.51(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.464(16) . ?
C21 C22 1.389(15) . ?
C21 C31 1.527(16) . ?
C22 N3 1.314(14) . ?
C23 C28 1.381(6) . ?
C23 C24 1.390(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.381(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.391(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.555(15) . ?
C29 N4 1.392(15) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 O3 1.218(14) . ?
C30 N4 1.357(15) . ?
C30 C31 1.547(15) . ?
C31 C32 1.518(15) . ?
C32 C33 1.374(15) . ?
C32 C37 1.385(16) . ?
C33 C34 1.441(16) . ?
C33 H33 0.9300 . ?
C34 C35 1.346(17) . ?
C34 F1 1.346(15) . ?
C35 C36 1.392(18) . ?
C35 H35 0.9300 . ?
C36 C37 1.354(15) . ?
C36 H36 0.9300 . ?
C37 N4 1.478(15) . ?
C38 N5 1.514(16) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.381(6) . ?
C39 C44 1.383(6) . ?
C39 N5 1.423(13) . ?
C40 C41 1.388(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.381(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.388(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.391(6) . ?
C43 H43 0.9300 . ?
C44 C45 1.451(13) . ?
C45 C46 1.360(15) . ?
C45 C48 1.501(14) . ?
C46 N5 1.321(14) . ?
C46 H46 0.9300 . ?
C47 O4 1.226(12) . ?
C47 N6 1.326(13) . ?
C47 C48 1.542(15) . ?
C48 C59 1.491(15) . ?
C48 C49 1.604(15) . ?
C49 C50 1.456(15) . ?
C49 C68 1.579(14) . ?
C49 H49 0.9800 . ?
C50 O5 1.276(13) . ?
C50 N6 1.380(14) . ?
C51 N6 1.434(15) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 C53 1.381(15) . ?
C52 N7 1.399(14) . ?
C52 C57 1.429(16) . ?
C53 C54 1.440(19) . ?
C53 H53 0.9300 . ?
C54 C55 1.40(2) . ?
C54 H54 0.9300 . ?
C55 C56 1.420(18) . ?
C55 H55 0.9300 . ?
C56 C57 1.362(15) . ?
C56 H56 0.9300 . ?
C57 C58 1.421(14) . ?
C58 C59 1.337(14) . ?
C58 C68 1.523(14) . ?
C59 N7 1.389(13) . ?
C60 C65 1.330(16) . ?
C60 C61 1.43(2) . ?
C60 H60 0.9300 . ?
C61 C62 1.31(2) . ?
C61 H61 0.9300 . ?
C62 C63 1.32(2) . ?
C62 H62 0.9300 . ?
C63 C64 1.362(17) . ?
C63 H63 0.9300 . ?
C64 C65 1.336(16) . ?
C64 H64 0.9300 . ?
C65 C66 1.549(16) . ?
C66 N8 1.460(13) . ?
C66 H66A 0.9700 . ?
C66 H66B 0.9700 . ?
C67 O6 1.191(13) . ?
C67 N8 1.373(13) . ?
C67 C68 1.560(14) . ?
C68 C69 1.560(15) . ?
C69 C74 1.366(16) . ?
C69 C70 1.383(15) . ?
C70 C71 1.362(14) . ?
C70 H70 0.9300 . ?
C71 F2 1.329(13) . ?
C71 C72 1.443(15) . ?
C72 C73 1.391(15) . ?
C72 H72 0.9300 . ?
C73 C74 1.449(15) . ?
C73 H73 0.9300 . ?
C74 N8 1.355(14) . ?
N3 H3A 0.8600 . ?
N7 H7 0.8600 . ?
