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#$Date: 2024-12-06 17:37:49 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296336 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/37/7133736.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_7133736
loop_
_publ_author_name
'Sreelekha, Mariswamy K.'
'Jijin, Robert K.'
'Nayak, Kalinga H.'
'Babu, Beneesh P.'
_publ_section_title
;
 Base-promoted multicomponent synthesis of 1,2,4-triazole-based hybrids
 from 1,3-diones, β-nitrostyrenes, and hydrazones.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11718
_journal_page_last               11721
_journal_paper_doi               10.1039/d4cc03709j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C30 H20 F N3 O3'
_chemical_formula_sum            'C30 H20 F N3 O3'
_chemical_formula_weight         489.49
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-06-21 deposited with the CCDC.	2024-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.972(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9993(7)
_cell_length_b                   14.9425(12)
_cell_length_c                   14.7473(10)
_cell_measurement_reflns_used    6005
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      47.651
_cell_measurement_theta_min      5.212
_cell_volume                     2414.7(3)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28442
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.507
_diffrn_reflns_theta_min         1.386
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     669
_refine_ls_number_reflns         11861
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.0688
_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)+(0.1228P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.2218
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                6179
_reflns_number_total             11861
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03709j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7133736.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7133736
_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   0.964
_shelx_estimated_absorpt_t_max   0.982
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 0.5156(5) 0.3822(4) -0.0893(4) 0.0456(14) Uani 1 1 d . . . . .
C2 C 0.4235(7) 0.3756(5) -0.1600(4) 0.0638(19) Uani 1 1 d . . . . .
H2 H 0.4400 0.3514 -0.2158 0.077 Uiso 1 1 calc R U . . .
C3 C 0.3102(6) 0.4046(6) -0.1468(5) 0.070(2) Uani 1 1 d . . . . .
H3 H 0.2488 0.3997 -0.1940 0.084 Uiso 1 1 calc R U . . .
C4 C 0.2836(6) 0.4409(6) -0.0665(5) 0.072(2) Uani 1 1 d . . . . .
H4 H 0.2048 0.4606 -0.0592 0.087 Uiso 1 1 calc R U . . .
C5 C 0.3733(5) 0.4484(5) 0.0039(4) 0.0569(17) Uani 1 1 d . . . . .
H5 H 0.3554 0.4735 0.0589 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4928(5) 0.4180(4) -0.0072(4) 0.0407(13) Uani 1 1 d . . . . .
C7 C 0.5910(4) 0.4232(4) 0.0638(3) 0.0360(12) Uani 1 1 d . . . . .
C8 C 0.7064(4) 0.3993(4) 0.0482(3) 0.0352(12) Uani 1 1 d . . . . .
C9 C 0.7280(6) 0.3639(4) -0.0412(4) 0.0469(14) Uani 1 1 d . . . . .
C10 C 0.8237(4) 0.4141(4) 0.1090(3) 0.0389(13) Uani 1 1 d . . . . .
H10 H 0.8846 0.3752 0.0843 0.047 Uiso 1 1 calc R U . . .
C11 C 0.8220(4) 0.3879(4) 0.2050(3) 0.0362(12) Uani 1 1 d . . . . .
C12 C 0.7724(5) 0.3655(4) 0.3405(3) 0.0391(12) Uani 1 1 d . . . . .
C13 C 0.6967(5) 0.3582(4) 0.4151(3) 0.0414(12) Uani 1 1 d . . . . .
C14 C 0.5713(6) 0.3580(6) 0.4004(4) 0.062(2) Uani 1 1 d . . . . .
H14 H 0.5351 0.3612 0.3411 0.075 Uiso 1 1 calc R U . . .
C15 C 0.4984(7) 0.3533(6) 0.4713(5) 0.076(2) Uani 1 1 d . . . . .
H15 H 0.4139 0.3523 0.4605 0.091 Uiso 1 1 calc R U . . .
C16 C 0.5520(7) 0.3501(5) 0.5569(4) 0.068(2) Uani 1 1 d . . . . .
C17 C 0.6751(7) 0.3494(6) 0.5751(4) 0.069(2) Uani 1 1 d . . . . .
H17 H 0.7092 0.3461 0.6350 0.083 Uiso 1 1 calc R U . . .
C18 C 0.7487(6) 0.3537(5) 0.5048(4) 0.0540(16) Uani 1 1 d . . . . .
H18 H 0.8331 0.3536 0.5168 0.065 Uiso 1 1 calc R U . . .
C19 C 0.8260(6) 0.5781(5) 0.1472(5) 0.0648(19) Uani 1 1 d . . . . .
H19 H 0.7683 0.5671 0.1884 0.078 Uiso 1 1 calc R U . . .
C20 C 0.8677(9) 0.6663(6) 0.1340(6) 0.088(3) Uani 1 1 d . . . . .
H20 H 0.8365 0.7135 0.1659 0.106 Uiso 1 1 calc R U . . .
C21 C 0.9528(9) 0.6818(8) 0.0751(6) 0.092(3) Uani 1 1 d . . . . .
H21 H 0.9815 0.7396 0.0675 0.111 Uiso 1 1 calc R U . . .
C22 C 0.9959(8) 0.6147(9) 0.0277(7) 0.096(3) Uani 1 1 d . . . . .
H22 H 1.0526 0.6263 -0.0141 0.115 Uiso 1 1 calc R U . . .
C23 C 0.9567(6) 0.5270(6) 0.0403(5) 0.073(2) Uani 1 1 d . . . . .
H23 H 0.9896 0.4807 0.0082 0.087 Uiso 1 1 calc R U . . .
C24 C 0.8709(4) 0.5084(4) 0.0990(4) 0.0450(14) Uani 1 1 d . . . . .
C25 C 1.0470(5) 0.3642(4) 0.2398(4) 0.0424(13) Uani 1 1 d . . . . .
C26 C 1.1312(6) 0.4173(5) 0.2871(5) 0.0677(19) Uani 1 1 d . . . . .
H26 H 1.1078 0.4566 0.3312 0.081 Uiso 1 1 calc R U . . .
C27 C 1.2531(6) 0.4115(6) 0.2680(6) 0.079(2) Uani 1 1 d . . . . .
H27 H 1.3121 0.4465 0.3000 0.094 Uiso 1 1 calc R U . . .
C28 C 1.2849(6) 0.3545(6) 0.2024(6) 0.074(2) Uani 1 1 d . . . . .
H28 H 1.3662 0.3508 0.1899 0.088 Uiso 1 1 calc R U . . .
C29 C 1.2002(6) 0.3029(6) 0.1549(5) 0.068(2) Uani 1 1 d . . . . .
H29 H 1.2231 0.2652 0.1092 0.082 Uiso 1 1 calc R U . . .
C30 C 1.0803(5) 0.3065(5) 0.1746(4) 0.0512(15) Uani 1 1 d . . . . .
H30 H 1.0223 0.2698 0.1437 0.061 Uiso 1 1 calc R U . . .
C31 C 0.6026(5) 0.5624(5) 0.7594(5) 0.0628(19) Uani 1 1 d . . . . .
H31 H 0.6219 0.5367 0.7051 0.075 Uiso 1 1 calc R U . . .
C32 C 0.6894(7) 0.5680(6) 0.8323(6) 0.078(2) Uani 1 1 d . . . . .
H32 H 0.7667 0.5442 0.8273 0.093 Uiso 1 1 calc R U . . .
C33 C 0.6637(8) 0.6082(7) 0.9119(5) 0.083(3) Uani 1 1 d . . . . .
H33 H 0.7235 0.6117 0.9604 0.100 Uiso 1 1 calc R U . . .
C34 C 0.5494(8) 0.6434(6) 0.9202(4) 0.074(2) Uani 1 1 d . . . . .
H34 H 0.5319 0.6725 0.9733 0.088 Uiso 1 1 calc R U . . .
C35 C 0.4613(5) 0.6346(5) 0.8478(4) 0.0486(15) Uani 1 1 d . . . . .
C36 C 0.4856(5) 0.5955(4) 0.7677(4) 0.0468(15) Uani 1 1 d . . . . .
C37 C 0.3879(5) 0.5894(4) 0.6953(4) 0.0414(13) Uani 1 1 d . . . . .
C38 C 0.2734(5) 0.6165(4) 0.7105(3) 0.0378(12) Uani 1 1 d . . . . .
C39 C 0.2519(6) 0.6556(4) 0.7962(4) 0.0460(14) Uani 1 1 d . . . . .
C40 C 0.1548(4) 0.6009(4) 0.6490(3) 0.0376(12) Uani 1 1 d . . . . .
H40 H 0.0945 0.6424 0.6704 0.045 Uiso 1 1 calc R U . . .
C41 C 0.1585(5) 0.6192(4) 0.5500(3) 0.0384(12) Uani 1 1 d . . . . .
C43 C 0.2885(6) 0.6347(4) 0.3395(4) 0.0472(14) Uani 1 1 d . . . . .
C44 C 0.4121(6) 0.6294(6) 0.3549(5) 0.0625(19) Uani 1 1 d . . . . .
H44 H 0.4471 0.6218 0.4141 0.075 Uiso 1 1 calc R U . . .
C45 C 0.4863(7) 0.6351(6) 0.2842(5) 0.076(2) Uani 1 1 d . . . . .
H45 H 0.5707 0.6306 0.2951 0.091 Uiso 1 1 calc R U . . .
C46 C 0.4338(8) 0.6472(5) 0.1991(5) 0.072(2) Uani 1 1 d . . . . .
C47 C 0.3113(8) 0.6523(6) 0.1804(5) 0.074(2) Uani 1 1 d . . . . .
H47 H 0.2778 0.6598 0.1208 0.088 Uiso 1 1 calc R U . . .
C48 C 0.2373(7) 0.6462(5) 0.2506(4) 0.0592(17) Uani 1 1 d . . . . .
H48 H 0.1530 0.6497 0.2386 0.071 Uiso 1 1 calc R U . . .
C49 C -0.0671(5) 0.6397(4) 0.5102(3) 0.0397(13) Uani 1 1 d . . . . .
C50 C -0.1489(6) 0.5826(5) 0.4628(5) 0.068(2) Uani 1 1 d . . . . .
H50 H -0.1233 0.5427 0.4199 0.082 Uiso 1 1 calc R U . . .
C51 C -0.2691(6) 0.5869(5) 0.4811(7) 0.085(3) Uani 1 1 d . . . . .
H51 H -0.3260 0.5501 0.4491 0.102 Uiso 1 1 calc R U . . .
C52 C -0.3066(6) 0.6437(6) 0.5449(6) 0.073(2) Uani 1 1 d . . . . .
H52 H -0.3878 0.6445 0.5580 0.088 Uiso 1 1 calc R U . . .
C53 C -0.2255(6) 0.6985(6) 0.5888(4) 0.0657(19) Uani 1 1 d . . . . .
H53 H -0.2516 0.7382 0.6317 0.079 Uiso 1 1 calc R U . . .
C54 C -0.1035(5) 0.6979(5) 0.5720(4) 0.0540(16) Uani 1 1 d . . . . .
H54 H -0.0481 0.7367 0.6027 0.065 Uiso 1 1 calc R U . . .
C55 C 0.1055(5) 0.5074(4) 0.6635(3) 0.0426(14) Uani 1 1 d . . . . .
C56 C 0.0203(6) 0.4950(6) 0.7269(5) 0.068(2) Uani 1 1 d . . . . .
H56 H -0.0074 0.5435 0.7587 0.082 Uiso 1 1 calc R U . . .
C57 C -0.0233(7) 0.4086(9) 0.7422(7) 0.090(3) Uani 1 1 d . . . . .
H57 H -0.0795 0.3996 0.7850 0.108 Uiso 1 1 calc R U . . .
C58 C 0.0150(9) 0.3404(7) 0.6962(6) 0.087(3) Uani 1 1 d . . . . .
H58 H -0.0159 0.2837 0.7064 0.105 Uiso 1 1 calc R U . . .
C59 C 0.0995(9) 0.3502(6) 0.6335(5) 0.089(3) Uani 1 1 d . . . . .
H59 H 0.1258 0.3009 0.6022 0.106 Uiso 1 1 calc R U . . .
C60 C 0.1449(7) 0.4346(5) 0.6176(4) 0.0638(18) Uani 1 1 d . . . . .
H60 H 0.2024 0.4420 0.5755 0.077 Uiso 1 1 calc R U . . .
N1 N 0.7262(4) 0.3873(3) 0.2539(3) 0.0417(11) Uani 1 1 d . . . . .
N2 N 0.8913(4) 0.3543(4) 0.3475(3) 0.0448(11) Uani 1 1 d . . . . .
N3 N 0.9218(4) 0.3691(3) 0.2610(3) 0.0380(10) Uani 1 1 d . . . . .
N4 N 0.0585(4) 0.6355(3) 0.4924(3) 0.0402(11) Uani 1 1 d . . . . .
N5 N 0.0915(4) 0.6423(3) 0.4055(3) 0.0454(11) Uani 1 1 d . . . . .
C42 C 0.2101(5) 0.6308(4) 0.4139(3) 0.0423(13) Uani 1 1 d . . . . .
N7 N 0.2551(4) 0.6160(3) 0.5024(3) 0.0409(11) Uani 1 1 d . . . . .
O1 O 0.6297(4) 0.3545(3) -0.1046(3) 0.0584(12) Uani 1 1 d . . . . .
O2 O 0.8259(4) 0.3416(4) -0.0638(3) 0.0712(14) Uani 1 1 d . . . . .
O3 O 0.5567(3) 0.4542(3) 0.1427(2) 0.0524(11) Uani 1 1 d . . . . .
H3A H 0.6007 0.4327 0.1849 0.079 Uiso 1 1 calc R U . . .
O4 O 0.3485(4) 0.6670(3) 0.8608(3) 0.0587(12) Uani 1 1 d . . . . .
O5 O 0.1542(4) 0.6800(4) 0.8180(3) 0.0669(13) Uani 1 1 d . . . . .
O6 O 0.4215(4) 0.5545(3) 0.6190(3) 0.0593(12) Uani 1 1 d . . . . .
H6 H 0.3705 0.5665 0.5769 0.089 Uiso 1 1 calc R U . . .
F1 F 0.4788(5) 0.3446(4) 0.6260(3) 0.1066(18) Uani 1 1 d . . . . .
F2 F 0.5070(5) 0.6566(4) 0.1311(3) 0.1133(19) 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'
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'
H H 0.0000 0.0000 '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
O1 C1 C6 120.7(5) . . ?
O1 C1 C2 118.4(5) . . ?
C6 C1 C2 120.9(6) . . ?
C3 C2 C1 119.3(6) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.7(6) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 119.8(7) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.0(6) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.2(5) . . ?
C1 C6 C7 118.7(5) . . ?
C5 C6 C7 123.1(5) . . ?
O3 C7 C8 125.3(4) . . ?
O3 C7 C6 113.6(4) . . ?
C8 C7 C6 121.1(5) . . ?
C7 C8 C9 118.5(5) . . ?
C7 C8 C10 128.2(5) . . ?
C9 C8 C10 112.9(4) . . ?
O2 C9 O1 117.0(5) . . ?
O2 C9 C8 124.8(5) . . ?
O1 C9 C8 118.2(5) . . ?
C11 C10 C24 112.1(5) . . ?
C11 C10 C8 116.5(4) . . ?
C24 C10 C8 111.0(4) . . ?
C11 C10 H10 105.4 . . ?
C24 C10 H10 105.4 . . ?
C8 C10 H10 105.4 . . ?
N1 C11 N3 108.0(4) . . ?
N1 C11 C10 127.0(4) . . ?
N3 C11 C10 124.6(4) . . ?
N2 C12 N1 112.9(5) . . ?
N2 C12 C13 124.6(5) . . ?
N1 C12 C13 122.5(5) . . ?
C14 C13 C18 118.2(5) . . ?
C14 C13 C12 121.1(5) . . ?
C18 C13 C12 120.7(5) . . ?
C13 C14 C15 121.4(6) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 118.6(7) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 F1 117.8(7) . . ?
C15 C16 C17 122.3(6) . . ?
F1 C16 C17 119.9(7) . . ?
C16 C17 C18 119.6(6) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 119.8(6) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C24 C19 C20 119.9(7) . . ?
C24 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 119.9(9) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.4(9) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.5(9) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 121.0(9) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C19 118.2(7) . . ?
C23 C24 C10 120.9(6) . . ?
C19 C24 C10 120.8(5) . . ?
C26 C25 C30 121.0(6) . . ?
C26 C25 N3 118.6(6) . . ?
C30 C25 N3 120.4(5) . . ?
C25 C26 C27 118.8(7) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C28 C27 C26 119.6(7) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C29 C28 C27 121.1(6) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 119.7(7) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C25 C30 C29 119.7(6) . . ?
C25 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C32 C31 C36 119.5(7) . . ?
C32 C31 H31 120.2 . . ?
C36 C31 H31 120.2 . . ?
C33 C32 C31 121.0(8) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C34 C33 C32 120.1(6) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 118.5(7) . . ?
C33 C34 H34 120.7 . . ?
C35 C34 H34 120.7 . . ?
C36 C35 O4 121.6(5) . . ?
C36 C35 C34 122.1(6) . . ?
O4 C35 C34 116.3(6) . . ?
C35 C36 C31 118.7(5) . . ?
C35 C36 C37 118.4(5) . . ?
C31 C36 C37 122.9(6) . . ?
O6 C37 C38 126.1(5) . . ?
O6 C37 C36 114.0(5) . . ?
C38 C37 C36 119.8(5) . . ?
C37 C38 C39 119.6(5) . . ?
C37 C38 C40 127.3(5) . . ?
C39 C38 C40 112.7(5) . . ?
O5 C39 O4 115.5(5) . . ?
O5 C39 C38 125.4(5) . . ?
O4 C39 C38 119.1(5) . . ?
C41 C40 C55 110.3(4) . . ?
C41 C40 C38 117.1(4) . . ?
C55 C40 C38 110.4(4) . . ?
C41 C40 H40 106.1 . . ?
C55 C40 H40 106.1 . . ?
C38 C40 H40 106.1 . . ?
N7 C41 N4 108.7(4) . . ?
N7 C41 C40 127.2(5) . . ?
N4 C41 C40 124.0(4) . . ?
C44 C43 C48 118.8(6) . . ?
C44 C43 C42 121.4(5) . . ?
C48 C43 C42 119.9(6) . . ?
C43 C44 C45 121.2(7) . . ?
C43 C44 H44 119.4 . . ?
C45 C44 H44 119.4 . . ?
C46 C45 C44 118.5(8) . . ?
C46 C45 H45 120.8 . . ?
C44 C45 H45 120.8 . . ?
C47 C46 C45 122.5(6) . . ?
C47 C46 F2 119.4(7) . . ?
C45 C46 F2 118.1(8) . . ?
C46 C47 C48 119.1(7) . . ?
C46 C47 H47 120.4 . . ?
C48 C47 H47 120.4 . . ?
C47 C48 C43 120.0(7) . . ?
C47 C48 H48 120.0 . . ?
C43 C48 H48 120.0 . . ?
C54 C49 C50 121.5(5) . . ?
C54 C49 N4 120.2(5) . . ?
C50 C49 N4 118.4(5) . . ?
C51 C50 C49 117.8(7) . . ?
C51 C50 H50 121.1 . . ?
C49 C50 H50 121.1 . . ?
C52 C51 C50 121.3(6) . . ?
C52 C51 H51 119.3 . . ?
C50 C51 H51 119.3 . . ?
C53 C52 C51 119.3(7) . . ?
C53 C52 H52 120.3 . . ?
C51 C52 H52 120.3 . . ?
C52 C53 C54 121.7(7) . . ?
C52 C53 H53 119.2 . . ?
C54 C53 H53 119.2 . . ?
C49 C54 C53 118.4(6) . . ?
C49 C54 H54 120.8 . . ?
C53 C54 H54 120.8 . . ?
C60 C55 C56 119.1(6) . . ?
C60 C55 C40 121.9(5) . . ?
C56 C55 C40 119.0(6) . . ?
C55 C56 C57 119.4(8) . . ?
C55 C56 H56 120.3 . . ?
C57 C56 H56 120.3 . . ?
C58 C57 C56 120.1(8) . . ?
C58 C57 H57 120.0 . . ?
C56 C57 H57 120.0 . . ?
C57 C58 C59 122.0(8) . . ?
C57 C58 H58 119.0 . . ?
C59 C58 H58 119.0 . . ?
C58 C59 C60 119.1(9) . . ?
C58 C59 H59 120.4 . . ?
C60 C59 H59 120.4 . . ?
C55 C60 C59 120.3(7) . . ?
C55 C60 H60 119.8 . . ?
C59 C60 H60 119.8 . . ?
C11 N1 C12 105.0(4) . . ?
C12 N2 N3 103.3(4) . . ?
C11 N3 N2 110.7(4) . . ?
C11 N3 C25 128.5(4) . . ?
N2 N3 C25 120.8(4) . . ?
C41 N4 N5 109.6(4) . . ?
C41 N4 C49 129.7(4) . . ?
N5 N4 C49 120.6(4) . . ?
C42 N5 N4 104.2(4) . . ?
N5 C42 N7 112.6(5) . . ?
N5 C42 C43 125.0(5) . . ?
N7 C42 C43 122.3(5) . . ?
C41 N7 C42 104.9(4) . . ?
C1 O1 C9 122.6(4) . . ?
C7 O3 H3A 109.5 . . ?
C35 O4 C39 121.2(5) . . ?
C37 O6 H6 109.5 . . ?
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 O1 1.359(7) . ?
C1 C6 1.367(8) . ?
C1 C2 1.393(8) . ?
C2 C3 1.350(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.440(7) . ?
C7 O3 1.337(6) . ?
C7 C8 1.357(7) . ?
C8 C9 1.458(7) . ?
C8 C10 1.523(7) . ?
C9 O2 1.202(7) . ?
C9 O1 1.373(7) . ?
C10 C11 1.471(7) . ?
C10 C24 1.513(8) . ?
C10 H10 0.9800 . ?
C11 N1 1.327(6) . ?
C11 N3 1.345(6) . ?
C12 N2 1.314(7) . ?
C12 N1 1.372(6) . ?
C12 C13 1.442(8) . ?
C13 C14 1.378(8) . ?
C13 C18 1.396(7) . ?
C14 C15 1.374(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.346(10) . ?
C15 H15 0.9300 . ?
C16 F1 1.356(7) . ?
C16 C17 1.357(11) . ?
C17 C18 1.372(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.376(10) . ?
C19 C20 1.414(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.353(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.332(14) . ?
C21 H21 0.9300 . ?
C22 C23 1.396(14) . ?
C22 H22 0.9300 . ?
C23 C24 1.363(8) . ?
C23 H23 0.9300 . ?
C25 C26 1.364(9) . ?
C25 C30 1.364(9) . ?
C25 N3 1.440(6) . ?
C26 C27 1.396(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.357(12) . ?
C27 H27 0.9300 . ?
C28 C29 1.357(11) . ?
C28 H28 0.9300 . ?
C29 C30 1.375(8) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.376(9) . ?
C31 C36 1.394(9) . ?
C31 H31 0.9300 . ?
C32 C33 1.370(12) . ?
C32 H32 0.9300 . ?
C33 C34 1.378(12) . ?
C33 H33 0.9300 . ?
C34 C35 1.385(9) . ?
C34 H34 0.9300 . ?
C35 C36 1.365(9) . ?
C35 O4 1.361(8) . ?
C36 C37 1.451(7) . ?
C37 O6 1.322(7) . ?
C37 C38 1.360(7) . ?
C38 C39 1.430(8) . ?
C38 C40 1.541(7) . ?
C39 O5 1.205(7) . ?
C39 O4 1.375(7) . ?
C40 C41 1.489(7) . ?
C40 C55 1.521(8) . ?
C40 H40 0.9800 . ?
C41 N7 1.324(7) . ?
C41 N4 1.352(6) . ?
C43 C44 1.361(9) . ?
C43 C48 1.393(8) . ?
C43 C42 1.454(8) . ?
C44 C45 1.382(9) . ?
C44 H44 0.9300 . ?
C45 C46 1.348(11) . ?
C45 H45 0.9300 . ?
C46 C47 1.353(11) . ?
C46 F2 1.346(7) . ?
C47 C48 1.375(9) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 C54 1.345(8) . ?
C49 C50 1.385(9) . ?
C49 N4 1.430(6) . ?
C50 C51 1.374(10) . ?
C50 H50 0.9300 . ?
C51 C52 1.358(11) . ?
C51 H51 0.9300 . ?
C52 C53 1.336(11) . ?
C52 H52 0.9300 . ?
C53 C54 1.386(9) . ?
C53 H53 0.9300 . ?
C54 H54 0.9300 . ?
C55 C60 1.370(9) . ?
C55 C56 1.392(9) . ?
C56 C57 1.402(13) . ?
C56 H56 0.9300 . ?
C57 C58 1.314(14) . ?
C57 H57 0.9300 . ?
C58 C59 1.374(13) . ?
C58 H58 0.9300 . ?
C59 C60 1.384(11) . ?
C59 H59 0.9300 . ?
C60 H60 0.9300 . ?
N2 N3 1.364(6) . ?
N4 N5 1.365(6) . ?
N5 C42 1.310(7) . ?
C42 N7 1.374(7) . ?
O3 H3A 0.8200 . ?
O6 H6 0.8200 . ?
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
O1 C1 C2 C3 -178.5(6) . . . . ?
C6 C1 C2 C3 -0.3(10) . . . . ?
C1 C2 C3 C4 0.5(12) . . . . ?
C2 C3 C4 C5 -0.2(13) . . . . ?
C3 C4 C5 C6 -0.3(11) . . . . ?
O1 C1 C6 C5 178.0(6) . . . . ?
C2 C1 C6 C5 -0.2(9) . . . . ?
O1 C1 C6 C7 -2.0(9) . . . . ?
C2 C1 C6 C7 179.9(6) . . . . ?
C4 C5 C6 C1 0.5(10) . . . . ?
C4 C5 C6 C7 -179.6(6) . . . . ?
C1 C6 C7 O3 -176.1(5) . . . . ?
C5 C6 C7 O3 4.0(8) . . . . ?
C1 C6 C7 C8 4.8(8) . . . . ?
C5 C6 C7 C8 -175.2(6) . . . . ?
O3 C7 C8 C9 178.0(6) . . . . ?
C6 C7 C8 C9 -2.9(8) . . . . ?
O3 C7 C8 C10 -9.8(10) . . . . ?
C6 C7 C8 C10 169.2(5) . . . . ?
C7 C8 C9 O2 178.9(6) . . . . ?
C10 C8 C9 O2 5.5(9) . . . . ?
C7 C8 C9 O1 -1.5(8) . . . . ?
C10 C8 C9 O1 -174.9(5) . . . . ?
C7 C8 C10 C11 49.1(8) . . . . ?
C9 C8 C10 C11 -138.4(5) . . . . ?
C7 C8 C10 C24 -80.8(7) . . . . ?
C9 C8 C10 C24 91.7(6) . . . . ?
C24 C10 C11 N1 100.0(6) . . . . ?
C8 C10 C11 N1 -29.5(8) . . . . ?
C24 C10 C11 N3 -72.6(7) . . . . ?
C8 C10 C11 N3 158.0(5) . . . . ?
N2 C12 C13 C14 -170.5(6) . . . . ?
N1 C12 C13 C14 11.0(9) . . . . ?
N2 C12 C13 C18 11.4(9) . . . . ?
N1 C12 C13 C18 -167.1(6) . . . . ?
C18 C13 C14 C15 -0.2(11) . . . . ?
C12 C13 C14 C15 -178.4(8) . . . . ?
C13 C14 C15 C16 1.0(13) . . . . ?
C14 C15 C16 F1 -179.4(8) . . . . ?
C14 C15 C16 C17 -1.5(13) . . . . ?
C15 C16 C17 C18 1.2(13) . . . . ?
F1 C16 C17 C18 179.0(7) . . . . ?
C16 C17 C18 C13 -0.4(11) . . . . ?
C14 C13 C18 C17 -0.1(10) . . . . ?
C12 C13 C18 C17 178.1(6) . . . . ?
C24 C19 C20 C21 -1.0(12) . . . . ?
C19 C20 C21 C22 1.5(14) . . . . ?
C20 C21 C22 C23 -2.0(15) . . . . ?
C21 C22 C23 C24 2.1(13) . . . . ?
C22 C23 C24 C19 -1.6(10) . . . . ?
C22 C23 C24 C10 176.8(7) . . . . ?
C20 C19 C24 C23 1.0(10) . . . . ?
C20 C19 C24 C10 -177.4(6) . . . . ?
C11 C10 C24 C23 132.8(6) . . . . ?
C8 C10 C24 C23 -95.0(6) . . . . ?
C11 C10 C24 C19 -48.9(7) . . . . ?
C8 C10 C24 C19 83.3(6) . . . . ?
C30 C25 C26 C27 -0.3(10) . . . . ?
N3 C25 C26 C27 178.8(6) . . . . ?
C25 C26 C27 C28 0.9(11) . . . . ?
C26 C27 C28 C29 0.0(12) . . . . ?
C27 C28 C29 C30 -1.5(12) . . . . ?
C26 C25 C30 C29 -1.2(10) . . . . ?
N3 C25 C30 C29 179.7(6) . . . . ?
C28 C29 C30 C25 2.1(11) . . . . ?
C36 C31 C32 C33 -2.0(11) . . . . ?
C31 C32 C33 C34 0.3(12) . . . . ?
C32 C33 C34 C35 2.1(12) . . . . ?
C33 C34 C35 C36 -2.7(11) . . . . ?
C33 C34 C35 O4 177.2(6) . . . . ?
O4 C35 C36 C31 -178.9(6) . . . . ?
C34 C35 C36 C31 1.0(10) . . . . ?
O4 C35 C36 C37 0.4(9) . . . . ?
C34 C35 C36 C37 -179.7(6) . . . . ?
C32 C31 C36 C35 1.4(10) . . . . ?
C32 C31 C36 C37 -177.9(6) . . . . ?
C35 C36 C37 O6 177.0(6) . . . . ?
C31 C36 C37 O6 -3.7(8) . . . . ?
C35 C36 C37 C38 -4.7(8) . . . . ?
C31 C36 C37 C38 174.6(6) . . . . ?
O6 C37 C38 C39 -178.3(6) . . . . ?
C36 C37 C38 C39 3.6(8) . . . . ?
O6 C37 C38 C40 9.3(10) . . . . ?
C36 C37 C38 C40 -168.8(5) . . . . ?
C37 C38 C39 O5 -178.2(6) . . . . ?
C40 C38 C39 O5 -4.7(9) . . . . ?
C37 C38 C39 O4 1.6(8) . . . . ?
C40 C38 C39 O4 175.1(5) . . . . ?
C37 C38 C40 C41 -46.3(8) . . . . ?
C39 C38 C40 C41 140.8(5) . . . . ?
C37 C38 C40 C55 81.1(7) . . . . ?
C39 C38 C40 C55 -91.8(6) . . . . ?
C55 C40 C41 N7 -101.1(6) . . . . ?
C38 C40 C41 N7 26.3(8) . . . . ?
C55 C40 C41 N4 73.6(7) . . . . ?
C38 C40 C41 N4 -159.0(5) . . . . ?
C48 C43 C44 C45 -0.1(11) . . . . ?
C42 C43 C44 C45 -178.5(7) . . . . ?
C43 C44 C45 C46 0.9(12) . . . . ?
C44 C45 C46 C47 -1.3(13) . . . . ?
C44 C45 C46 F2 177.2(7) . . . . ?
C45 C46 C47 C48 1.0(12) . . . . ?
F2 C46 C47 C48 -177.5(7) . . . . ?
C46 C47 C48 C43 -0.2(11) . . . . ?
C44 C43 C48 C47 -0.2(10) . . . . ?
C42 C43 C48 C47 178.2(6) . . . . ?
C54 C49 C50 C51 -0.3(11) . . . . ?
N4 C49 C50 C51 179.5(6) . . . . ?
C49 C50 C51 C52 -1.4(13) . . . . ?
C50 C51 C52 C53 2.1(13) . . . . ?
C51 C52 C53 C54 -1.2(12) . . . . ?
C50 C49 C54 C53 1.2(10) . . . . ?
N4 C49 C54 C53 -178.6(6) . . . . ?
C52 C53 C54 C49 -0.5(11) . . . . ?
C41 C40 C55 C60 45.5(7) . . . . ?
C38 C40 C55 C60 -85.6(6) . . . . ?
C41 C40 C55 C56 -136.1(5) . . . . ?
C38 C40 C55 C56 92.8(6) . . . . ?
C60 C55 C56 C57 -0.1(10) . . . . ?
C40 C55 C56 C57 -178.5(6) . . . . ?
C55 C56 C57 C58 -0.8(12) . . . . ?
C56 C57 C58 C59 1.1(14) . . . . ?
C57 C58 C59 C60 -0.6(14) . . . . ?
C56 C55 C60 C59 0.6(10) . . . . ?
C40 C55 C60 C59 179.0(6) . . . . ?
C58 C59 C60 C55 -0.3(12) . . . . ?
N3 C11 N1 C12 -1.3(6) . . . . ?
C10 C11 N1 C12 -174.9(6) . . . . ?
N2 C12 N1 C11 1.1(6) . . . . ?
C13 C12 N1 C11 179.8(5) . . . . ?
N1 C12 N2 N3 -0.4(6) . . . . ?
C13 C12 N2 N3 -179.0(5) . . . . ?
N1 C11 N3 N2 1.2(6) . . . . ?
C10 C11 N3 N2 174.9(5) . . . . ?
N1 C11 N3 C25 -178.5(5) . . . . ?
C10 C11 N3 C25 -4.7(9) . . . . ?
C12 N2 N3 C11 -0.5(6) . . . . ?
C12 N2 N3 C25 179.2(5) . . . . ?
C26 C25 N3 C11 123.2(7) . . . . ?
C30 C25 N3 C11 -57.7(8) . . . . ?
C26 C25 N3 N2 -56.4(7) . . . . ?
C30 C25 N3 N2 122.7(6) . . . . ?
N7 C41 N4 N5 0.5(6) . . . . ?
C40 C41 N4 N5 -175.1(5) . . . . ?
N7 C41 N4 C49 176.0(5) . . . . ?
C40 C41 N4 C49 0.4(9) . . . . ?
C54 C49 N4 C41 57.7(8) . . . . ?
C50 C49 N4 C41 -122.2(7) . . . . ?
C54 C49 N4 N5 -127.3(6) . . . . ?
C50 C49 N4 N5 52.9(8) . . . . ?
C41 N4 N5 C42 -0.7(6) . . . . ?
C49 N4 N5 C42 -176.6(5) . . . . ?
N4 N5 C42 N7 0.6(6) . . . . ?
N4 N5 C42 C43 -178.3(5) . . . . ?
C44 C43 C42 N5 174.5(6) . . . . ?
C48 C43 C42 N5 -3.9(9) . . . . ?
C44 C43 C42 N7 -4.3(9) . . . . ?
C48 C43 C42 N7 177.3(6) . . . . ?
N4 C41 N7 C42 -0.1(6) . . . . ?
C40 C41 N7 C42 175.3(6) . . . . ?
N5 C42 N7 C41 -0.4(7) . . . . ?
C43 C42 N7 C41 178.6(5) . . . . ?
C6 C1 O1 C9 -2.6(9) . . . . ?
C2 C1 O1 C9 175.5(6) . . . . ?
O2 C9 O1 C1 -176.0(6) . . . . ?
C8 C9 O1 C1 4.4(9) . . . . ?
C36 C35 O4 C39 5.0(9) . . . . ?
C34 C35 O4 C39 -174.9(6) . . . . ?
O5 C39 O4 C35 173.9(6) . . . . ?
C38 C39 O4 C35 -6.0(8) . . . . ?
