#------------------------------------------------------------------------------
#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/43/4024363.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_4024363
loop_
_publ_author_name
'Leo A. Paquette'
'Robert D. Dura'
'Isabelle Modolo'
_publ_contact_author_address
;
Department of Chemistry
Ohio State University
Columbus, OH 43210
;
_publ_contact_author_name        'Paquette, Leo'
_publ_section_title
;
Contrasting Responses of Pyrido[2,1-a]isoindol-6-ones and Their Sultam
Counterparts to Photochemical Activation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1982
_journal_page_last               1987
_journal_paper_doi               10.1021/jo802476c
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C26 H22 N2 O4'
_chemical_formula_sum            'C26 H22 N2 O4'
_chemical_formula_weight         426.46
_chemical_name_common            'Paquette 1598'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2008-11-07T13:22:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                101.625(3)
_cell_angle_beta                 95.611(3)
_cell_angle_gamma                98.740(3)
_cell_formula_units_Z            4
_cell_length_a                   8.6296(1)
_cell_length_b                   13.9375(1)
_cell_length_c                   18.6870(2)
_cell_measurement_reflns_used    7599
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_measurement_wavelength     0.71073
_cell_volume                     2156.68(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.109142E-1
_diffrn_orient_matrix_UB_12      -0.145302E-1
_diffrn_orient_matrix_UB_13      0.503385E-1
_diffrn_orient_matrix_UB_21      0.67048E-1
_diffrn_orient_matrix_UB_22      0.670638E-1
_diffrn_orient_matrix_UB_23      0.198558E-1
_diffrn_orient_matrix_UB_31      -0.968358E-1
_diffrn_orient_matrix_UB_32      0.287893E-1
_diffrn_orient_matrix_UB_33      0.10492E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            51609
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.61
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'trapezoid-shaped chunk'
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         7626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.06
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0609P)²+0.2995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                5655
_reflns_number_total             7626
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802476c_si_002.cif
_cod_data_source_block           Paquette1598
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024363
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.7728(2) 0.59644(13) 0.54786(9) 0.0609(5) Uani 1 1 d . . .
C1B C 0.69004(17) 0.78352(11) 0.13564(9) 0.0427(4) Uani 1 1 d . . .
C2A C 0.6564(3) 0.59367(18) 0.48968(11) 0.0799(7) Uani 1 1 d . . .
H2A H 0.6247 0.5368 0.4523 0.096 Uiso 1 1 calc R . .
C2B C 0.73479(19) 0.72259(13) 0.07581(9) 0.0542(4) Uani 1 1 d . . .
H2B H 0.7956 0.7495 0.0438 0.065 Uiso 1 1 calc R . .
C3A C 0.5905(3) 0.6762(2) 0.48908(13) 0.0951(8) Uani 1 1 d . . .
H3A H 0.5113 0.6755 0.4513 0.114 Uiso 1 1 calc R . .
C3B C 0.6870(2) 0.62149(14) 0.06498(11) 0.0645(5) Uani 1 1 d . . .
H3B H 0.7138 0.5789 0.0248 0.077 Uiso 1 1 calc R . .
C4A C 0.6399(3) 0.76102(17) 0.54386(13) 0.0899(7) Uani 1 1 d . . .
H4A H 0.5938 0.8168 0.5423 0.108 Uiso 1 1 calc R . .
C4B C 0.5993(2) 0.58356(13) 0.11382(12) 0.0696(6) Uani 1 1 d . . .
H4B H 0.5699 0.5149 0.1066 0.083 Uiso 1 1 calc R . .
C5A C 0.7568(3) 0.76487(14) 0.60117(11) 0.0713(6) Uani 1 1 d . . .
H5A H 0.7913 0.8231 0.6371 0.086 Uiso 1 1 calc R . .
C5B C 0.5533(2) 0.64396(12) 0.17333(11) 0.0585(5) Uani 1 1 d . . .
H5B H 0.4945 0.6166 0.2058 0.07 Uiso 1 1 calc R . .
C6A C 0.8209(2) 0.68066(12) 0.60399(9) 0.0549(4) Uani 1 1 d . . .
C6B C 0.59670(17) 0.74595(11) 0.18351(9) 0.0420(4) Uani 1 1 d . . .
C7A C 0.9508(2) 0.66608(11) 0.65955(8) 0.0483(4) Uani 1 1 d . . .
C7B C 0.56902(17) 0.82859(10) 0.24497(8) 0.0400(3) Uani 1 1 d . . .
C8A C 0.8637(2) 0.52036(14) 0.56065(9) 0.0641(5) Uani 1 1 d . . .
C8B C 0.73435(17) 0.89156(12) 0.16104(9) 0.0453(4) Uani 1 1 d . . .
C9A C 1.1029(2) 0.73915(13) 0.65936(10) 0.0634(5) Uani 1 1 d . . .
H9A1 H 1.1818 0.7344 0.6978 0.095 Uiso 1 1 calc R . .
H9A2 H 1.0811 0.8057 0.6676 0.095 Uiso 1 1 calc R . .
H9A3 H 1.1409 0.7231 0.6126 0.095 Uiso 1 1 calc R . .
C9B C 0.6375(2) 0.81321(14) 0.31992(10) 0.0575(4) Uani 1 1 d . . .
H9B1 H 0.7479 0.81 0.32 0.086 Uiso 1 1 calc R . .
H9B2 H 0.5826 0.7522 0.3285 0.086 Uiso 1 1 calc R . .
H9B3 H 0.6249 0.8678 0.3581 0.086 Uiso 1 1 calc R . .
C10A C 1.0888(3) 0.51710(18) 0.64739(14) 0.0756(6) Uani 1 1 d . . .
H10A H 1.080(3) 0.4503(17) 0.6129(13) 0.092(7) Uiso 1 1 d . . .
C10B C 0.6868(2) 1.01210(13) 0.26611(11) 0.0572(5) Uani 1 1 d . . .
H10B H 0.757(2) 1.0572(14) 0.2408(10) 0.065(5) Uiso 1 1 d . . .
C11A C 0.91238(19) 0.66965(10) 0.73988(8) 0.0413(4) Uani 1 1 d . . .
H11A H 1.0081 0.6566 0.7663 0.05 Uiso 1 1 calc R . .
C11B C 0.39407(16) 0.84449(10) 0.24810(8) 0.0369(3) Uani 1 1 d . . .
H11B H 0.392 0.8787 0.2991 0.044 Uiso 1 1 calc R . .
C12A C 0.8890(2) 0.77309(11) 0.78328(8) 0.0453(4) Uani 1 1 d . . .
H12A H 0.9591 0.8271 0.77 0.054 Uiso 1 1 calc R . .
C12B C 0.27403(17) 0.74590(11) 0.23671(9) 0.0458(4) Uani 1 1 d . . .
H12B H 0.3212 0.696 0.2573 0.055 Uiso 1 1 calc R . .
C13A C 0.7188(2) 0.78500(13) 0.77073(10) 0.0595(5) Uani 1 1 d . . .
H13A H 0.6873 0.8364 0.7513 0.071 Uiso 1 1 calc R . .
C13B C 0.2137(2) 0.70771(13) 0.15554(11) 0.0584(5) Uani 1 1 d . . .
H13B H 0.226 0.6459 0.1291 0.07 Uiso 1 1 calc R . .
C14A C 0.6177(2) 0.71637(14) 0.78966(11) 0.0668(5) Uani 1 1 d . . .
H14A H 0.5097 0.717 0.7872 0.08 Uiso 1 1 calc R . .
C14B C 0.1425(2) 0.76981(14) 0.12582(10) 0.0591(5) Uani 1 1 d . . .
H14B H 0.093 0.7538 0.0774 0.071 Uiso 1 1 calc R . .
C15A C 0.6930(2) 0.63770(12) 0.81541(9) 0.0555(4) Uani 1 1 d . . .
H15A H 0.6144 0.5888 0.8295 0.067 Uiso 1 1 calc R . .
C15B C 0.14760(18) 0.86844(12) 0.17651(9) 0.0457(4) Uani 1 1 d . . .
H15B H 0.0937 0.9124 0.152 0.055 Uiso 1 1 calc R . .
C16A C 0.77635(19) 0.58745(11) 0.75067(8) 0.0462(4) Uani 1 1 d . . .
H16A H 0.8259 0.5355 0.7672 0.055 Uiso 1 1 calc R . .
C16B C 0.32741(17) 0.91238(11) 0.20033(8) 0.0413(4) Uani 1 1 d . . .
H16B H 0.3358 0.9787 0.232 0.05 Uiso 1 1 calc R . .
C17A C 0.6493(2) 0.53724(14) 0.68814(10) 0.0567(5) Uani 1 1 d . . .
H17A H 0.585(2) 0.5793(13) 0.6642(10) 0.060(5) Uiso 1 1 d . . .
C17B C 0.3992(2) 0.92490(16) 0.13167(11) 0.0581(5) Uani 1 1 d . . .
H17B H 0.412(2) 0.8635(14) 0.1010(11) 0.067(6) Uiso 1 1 d . . .
C18A C 0.9239(2) 0.77442(10) 0.86717(8) 0.0455(4) Uani 1 1 d . . .
C18B C 0.12791(18) 0.77090(11) 0.27417(10) 0.0482(4) Uani 1 1 d . . .
C19A C 1.0850(2) 0.75718(11) 0.89455(8) 0.0483(4) Uani 1 1 d . . .
C19B C 0.15944(19) 0.81536(13) 0.35580(10) 0.0536(4) Uani 1 1 d . . .
C20A C 1.2319(2) 0.81728(14) 0.90110(9) 0.0615(5) Uani 1 1 d . . .
H20A H 1.2422 0.8769 0.8855 0.074 Uiso 1 1 calc R . .
C20B C 0.2105(2) 0.77381(18) 0.41288(13) 0.0789(6) Uani 1 1 d . . .
H20B H 0.2318 0.7093 0.404 0.095 Uiso 1 1 calc R . .
C21A C 1.3621(3) 0.78580(18) 0.93146(11) 0.0803(6) Uani 1 1 d . . .
H21A H 1.4618 0.8243 0.9353 0.096 Uiso 1 1 calc R . .
C21B C 0.2288(3) 0.8310(3) 0.48341(15) 0.1026(9) Uani 1 1 d . . .
H21B H 0.2646 0.8047 0.5226 0.123 Uiso 1 1 calc R . .
C22A C 1.3478(3) 0.6987(2) 0.95622(12) 0.0904(7) Uani 1 1 d . . .
H22A H 1.4379 0.6795 0.9764 0.108 Uiso 1 1 calc R . .
C22B C 0.1955(3) 0.9266(2) 0.49774(12) 0.0977(8) Uani 1 1 d . . .
H22B H 0.2099 0.9633 0.5461 0.117 Uiso 1 1 calc R . .
C23A C 1.2022(3) 0.63946(16) 0.95173(11) 0.0796(7) Uani 1 1 d . . .
H23A H 1.1924 0.5809 0.9689 0.096 Uiso 1 1 calc R . .
C23B C 0.1412(2) 0.96798(17) 0.44112(11) 0.0731(6) Uani 1 1 d . . .
H23B H 0.1174 1.0319 0.4502 0.088 Uiso 1 1 calc R . .
C24A C 1.0715(2) 0.67029(12) 0.92074(8) 0.0547(5) Uani 1 1 d . . .
C24B C 0.12347(19) 0.91016(13) 0.36988(9) 0.0507(4) Uani 1 1 d . . .
C25A C 0.9051(3) 0.62097(12) 0.90579(8) 0.0575(5) Uani 1 1 d . . .
C25B C 0.08180(17) 0.93693(11) 0.29902(9) 0.0427(4) Uani 1 1 d . . .
C26A C 0.8910(2) 0.87010(12) 0.91567(10) 0.0585(5) Uani 1 1 d . . .
H26A H 0.7831 0.8766 0.9034 0.088 Uiso 1 1 calc R . .
H26B H 0.9601 0.9265 0.9073 0.088 Uiso 1 1 calc R . .
H26C H 0.9094 0.867 0.9666 0.088 Uiso 1 1 calc R . .
C26B C -0.0049(2) 0.67880(13) 0.25786(14) 0.0756(6) Uani 1 1 d . . .
H26D H -0.0917 0.6944 0.2838 0.113 Uiso 1 1 calc R . .
H26E H 0.0348 0.6248 0.2738 0.113 Uiso 1 1 calc R . .
H26F H -0.0404 0.6599 0.2059 0.113 Uiso 1 1 calc R . .
N1A N 0.96841(19) 0.56216(10) 0.62628(8) 0.0560(4) Uani 1 1 d . . .
N1B N 0.66527(14) 0.91617(9) 0.22607(7) 0.0435(3) Uani 1 1 d . . .
N2A N 0.81930(17) 0.68399(9) 0.87725(7) 0.0498(3) Uani 1 1 d . . .
N2B N 0.07951(14) 0.85409(9) 0.24403(7) 0.0424(3) Uani 1 1 d . . .
O1A O 0.8574(2) 0.43626(10) 0.52437(8) 0.0860(5) Uani 1 1 d . . .
O1B O 0.81319(13) 0.95082(9) 0.13406(7) 0.0605(3) Uani 1 1 d . . .
O2A O 1.1878(2) 0.55100(13) 0.70058(10) 0.0927(5) Uani 1 1 d . . .
O2B O 0.62718(17) 1.03743(9) 0.32111(8) 0.0735(4) Uani 1 1 d . . .
O3A O 0.61352(18) 0.44826(10) 0.66952(8) 0.0810(4) Uani 1 1 d . . .
O3B O 0.43095(19) 1.00455(13) 0.11597(10) 0.0980(5) Uani 1 1 d . . .
O4A O 0.8478(2) 0.53803(8) 0.91355(7) 0.0795(4) Uani 1 1 d . . .
O4B O 0.05990(14) 1.01784(8) 0.28841(6) 0.0568(3) 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 0 '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 0.006 '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
C6A C1A C2A 121.4(2) . . ?
C6A C1A C8A 109.21(17) . . ?
C2A C1A C8A 129.35(18) . . ?
C2B C1B C6B 122.26(15) . . ?
C2B C1B C8B 128.27(15) . . ?
C6B C1B C8B 109.41(14) . . ?
C3A C2A C1A 118.34(19) . . ?
C3A C2A H2A 120.8 . . ?
C1A C2A H2A 120.8 . . ?
C3B C2B C1B 118.31(16) . . ?
C3B C2B H2B 120.8 . . ?
C1B C2B H2B 120.8 . . ?
C2A C3A C4A 120.6(2) . . ?
C2A C3A H3A 119.7 . . ?
C4A C3A H3A 119.7 . . ?
C2B C3B C4B 119.68(17) . . ?
C2B C3B H3B 120.2 . . ?
C4B C3B H3B 120.2 . . ?
C3A C4A C5A 121.4(2) . . ?
C3A C4A H4A 119.3 . . ?
C5A C4A H4A 119.3 . . ?
C3B C4B C5B 122.29(17) . . ?
C3B C4B H4B 118.9 . . ?
C5B C4B H4B 118.9 . . ?
C6A C5A C4A 118.68(19) . . ?
C6A C5A H5A 120.7 . . ?
C4A C5A H5A 120.7 . . ?
C4B C5B C6B 118.52(16) . . ?
C4B C5B H5B 120.7 . . ?
C6B C5B H5B 120.7 . . ?
C5A C6A C1A 119.45(17) . . ?
C5A C6A C7A 128.97(15) . . ?
C1A C6A C7A 111.46(16) . . ?
C5B C6B C1B 118.86(15) . . ?
C5B C6B C7B 129.70(14) . . ?
C1B C6B C7B 111.25(13) . . ?
N1A C7A C6A 100.19(13) . . ?
N1A C7A C9A 110.48(14) . . ?
C6A C7A C9A 109.60(13) . . ?
N1A C7A C11A 108.19(11) . . ?
C6A C7A C11A 117.07(14) . . ?
C9A C7A C11A 110.76(13) . . ?
N1B C7B C6B 100.13(11) . . ?
N1B C7B C9B 110.48(12) . . ?
C6B C7B C9B 110.08(13) . . ?
N1B C7B C11B 110.24(11) . . ?
C6B C7B C11B 116.54(12) . . ?
C9B C7B C11B 109.06(12) . . ?
O1A C8A N1A 123.9(2) . . ?
O1A C8A C1A 129.70(19) . . ?
N1A C8A C1A 106.38(15) . . ?
O1B C8B N1B 124.82(15) . . ?
O1B C8B C1B 129.35(16) . . ?
N1B C8B C1B 105.83(12) . . ?
C7A C9A H9A1 109.5 . . ?
C7A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C7A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
C7B C9B H9B1 109.5 . . ?
C7B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
C7B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
O2A C10A N1A 125.1(2) . . ?
O2A C10A H10A 125.7(13) . . ?
N1A C10A H10A 109.2(13) . . ?
O2B C10B N1B 124.16(18) . . ?
O2B C10B H10B 126.8(10) . . ?
N1B C10B H10B 109.0(10) . . ?
C12A C11A C7A 115.37(12) . . ?
C12A C11A C16A 109.19(12) . . ?
C7A C11A C16A 116.92(12) . . ?
C12A C11A H11A 104.6 . . ?
C7A C11A H11A 104.6 . . ?
C16A C11A H11A 104.6 . . ?
C12B C11B C16B 109.16(12) . . ?
C12B C11B C7B 113.46(11) . . ?
C16B C11B C7B 118.50(11) . . ?
C12B C11B H11B 104.8 . . ?
C16B C11B H11B 104.8 . . ?
C7B C11B H11B 104.8 . . ?
C13A C12A C11A 110.63(13) . . ?
C13A C12A C18A 105.56(13) . . ?
C11A C12A C18A 107.21(11) . . ?
C13A C12A H12A 111.1 . . ?
C11A C12A H12A 111.1 . . ?
C18A C12A H12A 111.1 . . ?
C13B C12B C18B 105.69(13) . . ?
C13B C12B C11B 109.73(13) . . ?
C18B C12B C11B 107.46(11) . . ?
C13B C12B H12B 111.2 . . ?
C18B C12B H12B 111.3 . . ?
C11B C12B H12B 111.3 . . ?
C14A C13A C12A 114.45(16) . . ?
C14A C13A H13A 122.8 . . ?
C12A C13A H13A 122.8 . . ?
C14B C13B C12B 113.92(14) . . ?
C14B C13B H13B 123 . . ?
C12B C13B H13B 123 . . ?
C13A C14A C15A 113.67(17) . . ?
C13A C14A H14A 123.2 . . ?
C15A C14A H14A 123.2 . . ?
C13B C14B C15B 114.26(16) . . ?
C13B C14B H14B 122.9 . . ?
C15B C14B H14B 122.9 . . ?
N2A C15A C14A 109.73(14) . . ?
N2A C15A C16A 106.37(14) . . ?
C14A C15A C16A 107.08(14) . . ?
N2A C15A H15A 111.2 . . ?
C14A C15A H15A 111.2 . . ?
C16A C15A H15A 111.2 . . ?
N2B C15B C14B 109.98(13) . . ?
N2B C15B C16B 106.94(12) . . ?
C14B C15B C16B 105.32(12) . . ?
N2B C15B H15B 111.4 . . ?
C14B C15B H15B 111.4 . . ?
C16B C15B H15B 111.4 . . ?
C17A C16A C15A 107.14(14) . . ?
C17A C16A C11A 120.24(13) . . ?
C15A C16A C11A 106.30(12) . . ?
C17A C16A H16A 107.5 . . ?
C15A C16A H16A 107.5 . . ?
C11A C16A H16A 107.5 . . ?
C17B C16B C11B 118.97(12) . . ?
C17B C16B C15B 107.48(13) . . ?
C11B C16B C15B 106.55(12) . . ?
C17B C16B H16B 107.8 . . ?
C11B C16B H16B 107.8 . . ?
C15B C16B H16B 107.8 . . ?
O3A C17A C16A 122.25(19) . . ?
O3A C17A H17A 118.8(10) . . ?
C16A C17A H17A 118.7(10) . . ?
O3B C17B C16B 122.61(19) . . ?
O3B C17B H17B 123.7(12) . . ?
C16B C17B H17B 113.7(12) . . ?
N2A C18A C19A 101.94(12) . . ?
N2A C18A C26A 112.07(13) . . ?
C19A C18A C26A 108.84(13) . . ?
N2A C18A C12A 104.67(12) . . ?
C19A C18A C12A 117.06(13) . . ?
C26A C18A C12A 111.81(12) . . ?
N2B C18B C19B 102.18(12) . . ?
N2B C18B C26B 112.28(14) . . ?
C19B C18B C26B 110.10(15) . . ?
N2B C18B C12B 105.51(12) . . ?
C19B C18B C12B 115.85(14) . . ?
C26B C18B C12B 110.59(13) . . ?
C24A C19A C20A 120.09(17) . . ?
C24A C19A C18A 110.11(15) . . ?
C20A C19A C18A 129.61(15) . . ?
C20B C19B C24B 120.55(19) . . ?
C20B C19B C18B 129.48(18) . . ?
C24B C19B C18B 109.93(14) . . ?
C21A C20A C19A 117.98(19) . . ?
C21A C20A H20A 121 . . ?
C19A C20A H20A 121 . . ?
C21B C20B C19B 117.7(2) . . ?
C21B C20B H20B 121.1 . . ?
C19B C20B H20B 121.1 . . ?
C22A C21A C20A 121.5(2) . . ?
C22A C21A H21A 119.3 . . ?
C20A C21A H21A 119.3 . . ?
C20B C21B C22B 122.0(2) . . ?
C20B C21B H21B 119 . . ?
C22B C21B H21B 119 . . ?
C21A C22A C23A 121.2(2) . . ?
C21A C22A H22A 119.4 . . ?
C23A C22A H22A 119.4 . . ?
C23B C22B C21B 120.7(2) . . ?
C23B C22B H22B 119.6 . . ?
C21B C22B H22B 119.6 . . ?
C22A C23A C24A 117.5(2) . . ?
C22A C23A H23A 121.2 . . ?
C24A C23A H23A 121.2 . . ?
C22B C23B C24B 117.2(2) . . ?
C22B C23B H23B 121.4 . . ?
C24B C23B H23B 121.4 . . ?
C23A C24A C19A 121.7(2) . . ?
C23A C24A C25A 129.57(18) . . ?
C19A C24A C25A 108.68(15) . . ?
C19B C24B C23B 121.81(17) . . ?
C19B C24B C25B 108.55(15) . . ?
C23B C24B C25B 129.40(16) . . ?
O4A C25A N2A 124.21(19) . . ?
O4A C25A C24A 128.47(18) . . ?
N2A C25A C24A 107.27(13) . . ?
O4B C25B N2B 124.57(15) . . ?
O4B C25B C24B 127.98(15) . . ?
N2B C25B C24B 107.36(13) . . ?
C18A C26A H26A 109.5 . . ?
C18A C26A H26B 109.5 . . ?
H26A C26A H26B 109.5 . . ?
C18A C26A H26C 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C18B C26B H26D 109.5 . . ?
C18B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C18B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
C10A N1A C8A 121.39(18) . . ?
C10A N1A C7A 124.83(17) . . ?
C8A N1A C7A 112.76(15) . . ?
C10B N1B C8B 121.58(14) . . ?
C10B N1B C7B 125.11(14) . . ?
C8B N1B C7B 113.31(12) . . ?
C25A N2A C15A 116.92(13) . . ?
C25A N2A C18A 111.69(14) . . ?
C15A N2A C18A 115.04(12) . . ?
C25B N2B C15B 118.15(12) . . ?
C25B N2B C18B 111.68(13) . . ?
C15B N2B C18B 114.35(11) . . ?
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
C1A C6A 1.386(2) . ?
C1A C2A 1.396(3) . ?
C1A C8A 1.455(3) . ?
C1B C2B 1.386(2) . ?
C1B C6B 1.387(2) . ?
C1B C8B 1.463(2) . ?
C2A C3A 1.360(3) . ?
C2A H2A 0.93 . ?
C2B C3B 1.374(3) . ?
C2B H2B 0.93 . ?
C3A C4A 1.379(3) . ?
C3A H3A 0.93 . ?
C3B C4B 1.376(3) . ?
C3B H3B 0.93 . ?
C4A C5A 1.384(3) . ?
C4A H4A 0.93 . ?
C4B C5B 1.383(3) . ?
C4B H4B 0.93 . ?
C5A C6A 1.380(3) . ?
C5A H5A 0.93 . ?
C5B C6B 1.383(2) . ?
C5B H5B 0.93 . ?
C6A C7A 1.517(2) . ?
C6B C7B 1.519(2) . ?
C7A N1A 1.493(2) . ?
C7A C9A 1.535(2) . ?
C7A C11A 1.561(2) . ?
C7B N1B 1.4925(18) . ?
C7B C9B 1.534(2) . ?
C7B C11B 1.564(2) . ?
C8A O1A 1.220(2) . ?
C8A N1A 1.413(2) . ?
C8B O1B 1.2097(18) . ?
C8B N1B 1.409(2) . ?
C9A H9A1 0.96 . ?
C9A H9A2 0.96 . ?
C9A H9A3 0.96 . ?
C9B H9B1 0.96 . ?
C9B H9B2 0.96 . ?
C9B H9B3 0.96 . ?
C10A O2A 1.210(3) . ?
C10A N1A 1.359(3) . ?
C10A H10A 1.01(2) . ?
C10B O2B 1.208(2) . ?
C10B N1B 1.370(2) . ?
C10B H10B 1.02(2) . ?
C11A C12A 1.558(2) . ?
C11A C16A 1.569(2) . ?
C11A H11A 0.98 . ?
C11B C12B 1.553(2) . ?
C11B C16B 1.558(2) . ?
C11B H11B 0.98 . ?
C12A C13A 1.504(2) . ?
C12A C18A 1.563(2) . ?
C12A H12A 0.98 . ?
C12B C13B 1.514(3) . ?
C12B C18B 1.552(2) . ?
C12B H12B 0.98 . ?
C13A C14A 1.321(3) . ?
C13A H13A 0.93 . ?
C13B C14B 1.313(3) . ?
C13B H13B 0.93 . ?
C14A C15A 1.491(3) . ?
C14A H14A 0.93 . ?
C14B C15B 1.496(2) . ?
C14B H14B 0.93 . ?
C15A N2A 1.477(2) . ?
C15A C16A 1.567(2) . ?
C15A H15A 0.98 . ?
C15B N2B 1.479(2) . ?
C15B C16B 1.564(2) . ?
C15B H15B 0.98 . ?
C16A C17A 1.498(2) . ?
C16A H16A 0.98 . ?
C16B C17B 1.508(2) . ?
C16B H16B 0.98 . ?
C17A O3A 1.201(2) . ?
C17A H17A 1.002(18) . ?
C17B O3B 1.203(2) . ?
C17B H17B 0.957(19) . ?
C18A N2A 1.4909(19) . ?
C18A C19A 1.505(2) . ?
C18A C26A 1.536(2) . ?
C18B N2B 1.4833(19) . ?
C18B C19B 1.507(3) . ?
C18B C26B 1.543(2) . ?
C19A C24A 1.388(2) . ?
C19A C20A 1.389(3) . ?
C19B C20B 1.379(3) . ?
C19B C24B 1.383(2) . ?
C20A C21A 1.379(3) . ?
C20A H20A 0.93 . ?
C20B C21B 1.377(4) . ?
C20B H20B 0.93 . ?
C21A C22A 1.376(3) . ?
C21A H21A 0.93 . ?
C21B C22B 1.384(4) . ?
C21B H21B 0.93 . ?
C22A C23A 1.380(4) . ?
C22A H22A 0.93 . ?
C22B C23B 1.380(3) . ?
C22B H22B 0.93 . ?
C23A C24A 1.383(3) . ?
C23A H23A 0.93 . ?
C23B C24B 1.391(3) . ?
C23B H23B 0.93 . ?
C24A C25A 1.468(3) . ?
C24B C25B 1.473(2) . ?
C25A O4A 1.2286(19) . ?
C25A N2A 1.383(2) . ?
C25B O4B 1.2224(17) . ?
C25B N2B 1.3785(19) . ?
C26A H26A 0.96 . ?
C26A H26B 0.96 . ?
C26A H26C 0.96 . ?
C26B H26D 0.96 . ?
C26B H26E 0.96 . ?
C26B H26F 0.96 . ?
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
C6A C1A C2A C3A 0.1(3) . . . . ?
C8A C1A C2A C3A -178.3(2) . . . . ?
C6B C1B C2B C3B -1.3(2) . . . . ?
C8B C1B C2B C3B 175.74(16) . . . . ?
C1A C2A C3A C4A 1.3(4) . . . . ?
C1B C2B C3B C4B -1.1(3) . . . . ?
C2A C3A C4A C5A -0.4(4) . . . . ?
C2B C3B C4B C5B 1.6(3) . . . . ?
C3A C4A C5A C6A -1.9(4) . . . . ?
C3B C4B C5B C6B 0.4(3) . . . . ?
C4A C5A C6A C1A 3.1(3) . . . . ?
C4A C5A C6A C7A 178.82(19) . . . . ?
C2A C1A C6A C5A -2.3(3) . . . . ?
C8A C1A C6A C5A 176.39(16) . . . . ?
C2A C1A C6A C7A -178.70(16) . . . . ?
C8A C1A C6A C7A 0.0(2) . . . . ?
C4B C5B C6B C1B -2.7(3) . . . . ?
C4B C5B C6B C7B -177.09(16) . . . . ?
C2B C1B C6B C5B 3.3(2) . . . . ?
C8B C1B C6B C5B -174.31(14) . . . . ?
C2B C1B C6B C7B 178.63(14) . . . . ?
C8B C1B C6B C7B 1.06(17) . . . . ?
C5A C6A C7A N1A -175.77(18) . . . . ?
C1A C6A C7A N1A 0.19(17) . . . . ?
C5A C6A C7A C9A -59.6(2) . . . . ?
C1A C6A C7A C9A 116.38(16) . . . . ?
C5A C6A C7A C11A 67.6(2) . . . . ?
C1A C6A C7A C11A -116.42(16) . . . . ?
C5B C6B C7B N1B 172.54(16) . . . . ?
C1B C6B C7B N1B -2.19(15) . . . . ?
C5B C6B C7B C9B 56.2(2) . . . . ?
C1B C6B C7B C9B -118.53(14) . . . . ?
C5B C6B C7B C11B -68.6(2) . . . . ?
C1B C6B C7B C11B 116.63(14) . . . . ?
C6A C1A C8A O1A 179.96(17) . . . . ?
C2A C1A C8A O1A -1.5(3) . . . . ?
C6A C1A C8A N1A -0.19(19) . . . . ?
C2A C1A C8A N1A 178.36(18) . . . . ?
C2B C1B C8B O1B 3.3(3) . . . . ?
C6B C1B C8B O1B -179.29(16) . . . . ?
C2B C1B C8B N1B -176.73(15) . . . . ?
C6B C1B C8B N1B 0.66(16) . . . . ?
N1A C7A C11A C12A -179.68(13) . . . . ?
C6A C7A C11A C12A -67.53(17) . . . . ?
C9A C7A C11A C12A 59.10(19) . . . . ?
N1A C7A C11A C16A -49.22(18) . . . . ?
C6A C7A C11A C16A 62.92(18) . . . . ?
C9A C7A C11A C16A -170.45(14) . . . . ?
N1B C7B C11B C12B 157.35(12) . . . . ?
C6B C7B C11B C12B 44.16(17) . . . . ?
C9B C7B C11B C12B -81.19(16) . . . . ?
N1B C7B C11B C16B 27.36(17) . . . . ?
C6B C7B C11B C16B -85.82(16) . . . . ?
C9B C7B C11B C16B 148.82(13) . . . . ?
C7A C11A C12A C13A 89.09(16) . . . . ?
C16A C11A C12A C13A -44.99(17) . . . . ?
C7A C11A C12A C18A -156.28(13) . . . . ?
C16A C11A C12A C18A 69.63(15) . . . . ?
C16B C11B C12B C13B 44.26(16) . . . . ?
C7B C11B C12B C13B -90.27(15) . . . . ?
C16B C11B C12B C18B -70.19(15) . . . . ?
C7B C11B C12B C18B 155.28(13) . . . . ?
C11A C12A C13A C14A 58.17(19) . . . . ?
C18A C12A C13A C14A -57.49(19) . . . . ?
C18B C12B C13B C14B 56.09(18) . . . . ?
C11B C12B C13B C14B -59.49(18) . . . . ?
C12A C13A C14A C15A -3.5(2) . . . . ?
C12B C13B C14B C15B 4.9(2) . . . . ?
C13A C14A C15A N2A 55.9(2) . . . . ?
C13A C14A C15A C16A -59.1(2) . . . . ?
C13B C14B C15B N2B -56.24(19) . . . . ?
C13B C14B C15B C16B 58.66(19) . . . . ?
N2A C15A C16A C17A 178.23(13) . . . . ?
C14A C15A C16A C17A -64.50(17) . . . . ?
N2A C15A C16A C11A -52.03(16) . . . . ?
C14A C15A C16A C11A 65.24(17) . . . . ?
C12A C11A C16A C17A 108.77(16) . . . . ?
C7A C11A C16A C17A -24.5(2) . . . . ?
C12A C11A C16A C15A -12.96(17) . . . . ?
C7A C11A C16A C15A -146.25(14) . . . . ?
C12B C11B C16B C17B -106.33(16) . . . . ?
C7B C11B C16B C17B 25.6(2) . . . . ?
C12B C11B C16B C15B 15.19(15) . . . . ?
C7B C11B C16B C15B 147.10(12) . . . . ?
N2B C15B C16B C17B 178.57(13) . . . . ?
C14B C15B C16B C17B 61.58(17) . . . . ?
N2B C15B C16B C11B 50.00(14) . . . . ?
C14B C15B C16B C11B -66.98(15) . . . . ?
C15A C16A C17A O3A -109.61(19) . . . . ?
C11A C16A C17A O3A 129.07(18) . . . . ?
C11B C16B C17B O3B -135.51(17) . . . . ?
C15B C16B C17B O3B 103.4(2) . . . . ?
C13A C12A C18A N2A 64.27(15) . . . . ?
C11A C12A C18A N2A -53.71(15) . . . . ?
C13A C12A C18A C19A 176.22(13) . . . . ?
C11A C12A C18A C19A 58.25(16) . . . . ?
C13A C12A C18A C26A -57.26(17) . . . . ?
C11A C12A C18A C26A -175.24(13) . . . . ?
C13B C12B C18B N2B -65.06(15) . . . . ?
C11B C12B C18B N2B 52.06(16) . . . . ?
C13B C12B C18B C19B -177.26(13) . . . . ?
C11B C12B C18B C19B -60.14(17) . . . . ?
C13B C12B C18B C26B 56.58(18) . . . . ?
C11B C12B C18B C26B 173.70(14) . . . . ?
N2A C18A C19A C24A -3.03(16) . . . . ?
C26A C18A C19A C24A 115.52(14) . . . . ?
C12A C18A C19A C24A -116.52(14) . . . . ?
N2A C18A C19A C20A -177.95(15) . . . . ?
C26A C18A C19A C20A -59.4(2) . . . . ?
C12A C18A C19A C20A 68.6(2) . . . . ?
N2B C18B C19B C20B -179.05(17) . . . . ?
C26B C18B C19B C20B 61.5(2) . . . . ?
C12B C18B C19B C20B -64.9(2) . . . . ?
N2B C18B C19B C24B 3.27(16) . . . . ?
C26B C18B C19B C24B -116.21(15) . . . . ?
C12B C18B C19B C24B 117.39(15) . . . . ?
C24A C19A C20A C21A 2.4(2) . . . . ?
C18A C19A C20A C21A 176.93(16) . . . . ?
C24B C19B C20B C21B -2.0(3) . . . . ?
C18B C19B C20B C21B -179.47(19) . . . . ?
C19A C20A C21A C22A -1.4(3) . . . . ?
C19B C20B C21B C22B 0.9(4) . . . . ?
C20A C21A C22A C23A -0.1(3) . . . . ?
C20B C21B C22B C23B 0.4(4) . . . . ?
C21A C22A C23A C24A 0.6(3) . . . . ?
C21B C22B C23B C24B -0.7(3) . . . . ?
C22A C23A C24A C19A 0.4(3) . . . . ?
C22A C23A C24A C25A 176.91(18) . . . . ?
C20A C19A C24A C23A -2.0(2) . . . . ?
C18A C19A C24A C23A -177.46(15) . . . . ?
C20A C19A C24A C25A -179.13(14) . . . . ?
C18A C19A C24A C25A 5.39(17) . . . . ?
C20B C19B C24B C23B 1.8(3) . . . . ?
C18B C19B C24B C23B 179.71(15) . . . . ?
C20B C19B C24B C25B 176.69(16) . . . . ?
C18B C19B C24B C25B -5.39(18) . . . . ?
C22B C23B C24B C19B -0.4(3) . . . . ?
C22B C23B C24B C25B -174.14(19) . . . . ?
C23A C24A C25A O4A -5.0(3) . . . . ?
C19A C24A C25A O4A 171.81(16) . . . . ?
C23A C24A C25A N2A 177.49(17) . . . . ?
C19A C24A C25A N2A -5.65(17) . . . . ?
C19B C24B C25B O4B -171.33(15) . . . . ?
C23B C24B C25B O4B 3.1(3) . . . . ?
C19B C24B C25B N2B 5.44(17) . . . . ?
C23B C24B C25B N2B 179.83(17) . . . . ?
O2A C10A N1A C8A 175.83(19) . . . . ?
O2A C10A N1A C7A 8.2(3) . . . . ?
O1A C8A N1A C10A 11.2(3) . . . . ?
C1A C8A N1A C10A -168.67(16) . . . . ?
O1A C8A N1A C7A -179.81(15) . . . . ?
C1A C8A N1A C7A 0.33(18) . . . . ?
C6A C7A N1A C10A 168.24(16) . . . . ?
C9A C7A N1A C10A 52.7(2) . . . . ?
C11A C7A N1A C10A -68.7(2) . . . . ?
C6A C7A N1A C8A -0.32(16) . . . . ?
C9A C7A N1A C8A -115.85(15) . . . . ?
C11A C7A N1A C8A 122.75(14) . . . . ?
O2B C10B N1B C8B 178.11(17) . . . . ?
O2B C10B N1B C7B -1.6(3) . . . . ?
O1B C8B N1B C10B -1.9(2) . . . . ?
C1B C8B N1B C10B 178.10(14) . . . . ?
O1B C8B N1B C7B 177.75(14) . . . . ?
C1B C8B N1B C7B -2.20(16) . . . . ?
C6B C7B N1B C10B -177.64(14) . . . . ?
C9B C7B N1B C10B -61.60(19) . . . . ?
C11B C7B N1B C10B 59.02(18) . . . . ?
C6B C7B N1B C8B 2.67(15) . . . . ?
C9B C7B N1B C8B 118.72(14) . . . . ?
C11B C7B N1B C8B -120.67(13) . . . . ?
O4A C25A N2A C15A -38.4(2) . . . . ?
C24A C25A N2A C15A 139.20(14) . . . . ?
O4A C25A N2A C18A -173.86(14) . . . . ?
C24A C25A N2A C18A 3.74(16) . . . . ?
C14A C15A N2A C25A -177.66(14) . . . . ?
C16A C15A N2A C25A -62.17(17) . . . . ?
C14A C15A N2A C18A -43.65(18) . . . . ?
C16A C15A N2A C18A 71.84(16) . . . . ?
C19A C18A N2A C25A -0.58(15) . . . . ?
C26A C18A N2A C25A -116.80(15) . . . . ?
C12A C18A N2A C25A 121.83(13) . . . . ?
C19A C18A N2A C15A -136.94(13) . . . . ?
C26A C18A N2A C15A 106.84(15) . . . . ?
C12A C18A N2A C15A -14.52(17) . . . . ?
O4B C25B N2B C15B 37.8(2) . . . . ?
C24B C25B N2B C15B -139.07(13) . . . . ?
O4B C25B N2B C18B 173.56(14) . . . . ?
C24B C25B N2B C18B -3.35(16) . . . . ?
C14B C15B N2B C25B 176.70(13) . . . . ?
C16B C15B N2B C25B 62.83(16) . . . . ?
C14B C15B N2B C18B 42.10(17) . . . . ?
C16B C15B N2B C18B -71.76(15) . . . . ?
C19B C18B N2B C25B 0.21(15) . . . . ?
C26B C18B N2B C25B 118.14(16) . . . . ?
C12B C18B N2B C25B -121.31(13) . . . . ?
C19B C18B N2B C15B 137.70(13) . . . . ?
C26B C18B N2B C15B -104.36(16) . . . . ?
C12B C18B N2B C15B 16.19(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091064
