#------------------------------------------------------------------------------
#$Date: 2021-09-09 03:45:19 +0300 (Thu, 09 Sep 2021) $
#$Revision: 269057 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/34/7243496.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_7243496
loop_
_publ_author_name
'Ikeda, Kazuho'
'Yoo, Dongho'
'Nishikawa, Ryu'
'Kawamoto, Tadashi'
'Mori, Takehiko'
_publ_section_title
;
 Charge injected proton transfer in indigo derivatives
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D1CP03364F
_journal_year                    2021
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C16 H11 N O2'
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-05-18 deposited with the CCDC.	2021-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.315(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            16
_cell_length_a                   52.556(3)
_cell_length_b                   3.8744(3)
_cell_length_c                   24.2104(14)
_cell_measurement_reflns_used    3139
_cell_measurement_temperature    262
_cell_measurement_theta_max      67.85
_cell_measurement_theta_min      3.54
_cell_volume                     4797.3(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      262
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1274
_diffrn_reflns_av_unetI/netI     0.1386
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       60
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26122
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        62.600
_diffrn_reflns_theta_max         62.600
_diffrn_reflns_theta_min         3.457
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2080.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.73
_refine_diff_density_min         -0.66
_refine_ls_abs_structure_details
;
 Flack x determined using 842 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     686
_refine_ls_number_reflns         7164
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.1551
_refine_ls_R_factor_gt           0.1152
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2868
_refine_ls_wR_factor_ref         0.3500
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.870
_reflns_number_gt                4016
_reflns_number_total             7164
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d1cp03364f3.cif
_cod_data_source_block           20190121
_cod_original_cell_volume        4797.2(5)
_cod_database_code               7243496
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 +X,-Y,1/2+Z
3 1/2+X,1/2+Y,+Z
4 1/2+X,1/2-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
O1 O 0.8973(3) 0.830(4) 0.4835(6) 0.082(4) Uani 1 1 d . . . . .
O2 O 0.7701(4) 0.010(5) 0.6708(10) 0.110(6) Uani 1 1 d . . . . .
O3 O 0.8994(3) 0.095(5) 0.7209(6) 0.083(4) Uani 1 1 d . . . . .
O4 O 0.7816(3) 0.980(5) 0.9279(9) 0.104(6) Uani 1 1 d . . . . .
O5 O 0.5976(3) 0.067(4) 0.4536(6) 0.086(4) Uani 1 1 d . . . . .
O6 O 0.7322(3) 0.360(5) 0.7850(8) 0.103(5) Uani 1 1 d . . . . .
O7 O 0.6016(3) 0.235(4) 0.7142(6) 0.087(4) Uani 1 1 d . . . . .
O8 O 0.7245(3) 1.213(5) 1.0231(7) 0.102(5) Uani 1 1 d . . . . .
N1 N 0.9008(3) 0.399(4) 0.6116(6) 0.063(4) Uani 1 1 d . . . . .
H1A H 0.894773 0.299116 0.637640 0.075 Uiso 1 1 calc R U . . .
N2 N 0.8977(3) 0.079(4) 0.8659(7) 0.064(4) Uani 1 1 d . . . . .
H2A H 0.891015 0.104456 0.894943 0.076 Uiso 1 1 calc R U . . .
N3 N 0.6020(3) -0.025(4) 0.5994(6) 0.061(4) Uani 1 1 d . . . . .
H3A H 0.609376 -0.016842 0.634977 0.074 Uiso 1 1 calc R U . . .
N4 N 0.5978(3) 0.632(5) 0.8427(6) 0.065(4) Uani 1 1 d . . . . .
H4A H 0.603747 0.725208 0.875427 0.078 Uiso 1 1 calc R U . . .
C1 C 0.9762(4) 0.534(5) 0.5911(11) 0.075(6) Uani 1 1 d . . . . .
H1 H 0.992761 0.564011 0.584375 0.090 Uiso 1 1 calc R U . . .
C2 C 0.9722(4) 0.372(7) 0.6434(11) 0.084(6) Uani 1 1 d . . . . .
H2 H 0.986643 0.302271 0.671023 0.101 Uiso 1 1 calc R U . . .
C3 C 0.9547(3) 0.634(4) 0.5540(9) 0.054(4) Uani 1 1 d . . . . .
H3 H 0.956712 0.734815 0.520398 0.065 Uiso 1 1 calc R U . . .
C4 C 0.9484(4) 0.324(7) 0.6522(9) 0.078(6) Uani 1 1 d . . . . .
H4 H 0.946525 0.216211 0.685368 0.094 Uiso 1 1 calc R U . . .
C5 C 0.9295(3) 0.599(4) 0.5619(8) 0.051(4) Uani 1 1 d . . . . .
C6 C 0.9265(3) 0.430(5) 0.6134(8) 0.058(5) Uani 1 1 d . . . . .
C7 C 0.9038(3) 0.674(5) 0.5317(8) 0.060(4) Uani 1 1 d . . . . .
C8 C 0.8849(4) 0.544(4) 0.5633(9) 0.056(4) Uani 1 1 d . . . . .
C9 C 0.8592(3) 0.567(4) 0.5460(9) 0.056(5) Uani 1 1 d . . . . .
H9 H 0.854114 0.671312 0.510577 0.067 Uiso 1 1 calc R U . . .
C10 C 0.8370(4) 0.472(4) 0.5684(9) 0.059(4) Uani 1 1 d . . . . .
C11 C 0.8126(4) 0.531(5) 0.5394(8) 0.061(5) Uani 1 1 d . . . . .
H11 H 0.810201 0.633934 0.503830 0.073 Uiso 1 1 calc R U . . .
C12 C 0.8397(3) 0.283(5) 0.6211(9) 0.068(5) Uani 1 1 d . . . . .
H12 H 0.856170 0.217989 0.641998 0.081 Uiso 1 1 calc R U . . .
C13 C 0.7903(4) 0.448(5) 0.5590(9) 0.066(5) Uani 1 1 d . . . . .
H13 H 0.773727 0.512179 0.538616 0.079 Uiso 1 1 calc R U . . .
C14 C 0.8179(4) 0.200(5) 0.6399(8) 0.066(5) Uani 1 1 d . . . . .
H14 H 0.820210 0.094297 0.675193 0.079 Uiso 1 1 calc R U . . .
C15 C 0.7935(3) 0.261(5) 0.6110(9) 0.068(5) Uani 1 1 d . . . . .
C16 C 0.7701(4) 0.180(6) 0.6278(11) 0.082(6) Uani 1 1 d . . . . .
H16 H 0.754204 0.256417 0.605693 0.098 Uiso 1 1 calc R U . . .
C17 C 0.9669(4) -0.379(6) 0.8476(11) 0.077(6) Uani 1 1 d . . . . .
H17 H 0.982480 -0.474379 0.842483 0.092 Uiso 1 1 calc R U . . .
C18 C 0.9623(4) -0.358(6) 0.9015(11) 0.075(6) Uani 1 1 d . . . . .
H18 H 0.975039 -0.442394 0.931672 0.090 Uiso 1 1 calc R U . . .
C19 C 0.9488(4) -0.261(6) 0.8022(10) 0.074(6) Uani 1 1 d . . . . .
H19 H 0.951288 -0.281725 0.765490 0.089 Uiso 1 1 calc R U . . .
C20 C 0.9396(4) -0.219(5) 0.9134(10) 0.071(5) Uani 1 1 d . . . . .
H20 H 0.936237 -0.220064 0.949482 0.085 Uiso 1 1 calc R U . . .
C21 C 0.9262(3) -0.104(5) 0.8127(7) 0.057(4) Uani 1 1 d . . . . .
C22 C 0.9220(4) -0.074(5) 0.8647(9) 0.066(5) Uani 1 1 d . . . . .
C23 C 0.9036(3) 0.062(5) 0.7729(9) 0.059(5) Uani 1 1 d . . . . .
C24 C 0.8869(3) 0.178(5) 0.8109(8) 0.061(5) Uani 1 1 d . . . . .
C25 C 0.8637(3) 0.355(7) 0.7890(9) 0.074(5) Uani 1 1 d . . . . .
H25 H 0.860415 0.385015 0.749894 0.089 Uiso 1 1 calc R U . . .
C26 C 0.8434(3) 0.503(4) 0.8144(8) 0.051(4) Uani 1 1 d . . . . .
C27 C 0.8202(3) 0.603(5) 0.7797(9) 0.066(5) Uani 1 1 d . . . . .
H27 H 0.817615 0.576163 0.740618 0.079 Uiso 1 1 calc R U . . .
C28 C 0.8459(4) 0.549(5) 0.8727(9) 0.062(5) Uani 1 1 d . . . . .
H28 H 0.861434 0.480671 0.897238 0.074 Uiso 1 1 calc R U . . .
C29 C 0.8006(3) 0.744(5) 0.8021(9) 0.066(5) Uani 1 1 d . . . . .
H29 H 0.785171 0.814755 0.777645 0.080 Uiso 1 1 calc R U . . .
C30 C 0.8270(3) 0.689(6) 0.8952(8) 0.064(5) Uani 1 1 d . . . . .
H30 H 0.829655 0.721385 0.934150 0.077 Uiso 1 1 calc R U . . .
C31 C 0.8033(3) 0.783(5) 0.8586(8) 0.061(5) Uani 1 1 d . . . . .
C32 C 0.7820(4) 0.937(6) 0.8797(11) 0.073(6) Uani 1 1 d . . . . .
H32 H 0.767374 1.008124 0.852686 0.087 Uiso 1 1 calc R U . . .
C33 C 0.5294(4) -0.376(6) 0.5141(11) 0.083(6) Uani 1 1 d . . . . .
H33 H 0.513253 -0.452148 0.493398 0.100 Uiso 1 1 calc R U . . .
C34 C 0.5362(4) -0.390(6) 0.5739(9) 0.068(5) Uani 1 1 d . . . . .
H34 H 0.523825 -0.479724 0.592014 0.082 Uiso 1 1 calc R U . . .
C35 C 0.5473(4) -0.248(5) 0.4885(10) 0.076(6) Uani 1 1 d . . . . .
H35 H 0.543154 -0.228333 0.449163 0.091 Uiso 1 1 calc R U . . .
C36 C 0.5598(4) -0.279(5) 0.6079(10) 0.072(5) Uani 1 1 d . . . . .
H36 H 0.563611 -0.291207 0.647286 0.087 Uiso 1 1 calc R U . . .
C37 C 0.5720(4) -0.144(5) 0.5183(8) 0.063(5) Uani 1 1 d . . . . .
C38 C 0.5773(3) -0.148(5) 0.5771(8) 0.055(4) Uani 1 1 d . . . . .
C39 C 0.5941(4) 0.010(4) 0.5020(9) 0.057(4) Uani 1 1 d . . . . .
C40 C 0.6135(3) 0.085(5) 0.5550(9) 0.062(5) Uani 1 1 d . . . . .
C41 C 0.6379(3) 0.218(5) 0.5589(9) 0.064(5) Uani 1 1 d . . . . .
H41 H 0.641060 0.282180 0.524066 0.077 Uiso 1 1 calc R U . . .
C42 C 0.6596(3) 0.279(6) 0.6063(8) 0.066(5) Uani 1 1 d . . . . .
C43 C 0.6815(4) 0.451(5) 0.5942(11) 0.077(6) Uani 1 1 d . . . . .
H43 H 0.680537 0.531260 0.557560 0.092 Uiso 1 1 calc R U . . .
C44 C 0.6613(3) 0.187(5) 0.6622(7) 0.056(4) Uani 1 1 d . . . . .
H44 H 0.646579 0.094832 0.672016 0.067 Uiso 1 1 calc R U . . .
C45 C 0.7044(4) 0.503(5) 0.6357(9) 0.066(5) Uani 1 1 d . . . . .
H45 H 0.718892 0.607858 0.626652 0.079 Uiso 1 1 calc R U . . .
C46 C 0.6834(3) 0.227(6) 0.7030(8) 0.069(5) Uani 1 1 d . . . . .
H46 H 0.684083 0.142253 0.739258 0.083 Uiso 1 1 calc R U . . .
C47 C 0.7052(3) 0.392(5) 0.6920(9) 0.058(4) Uani 1 1 d . . . . .
C48 C 0.7288(4) 0.442(6) 0.7354(11) 0.074(6) Uani 1 1 d . . . . .
H48 H 0.742703 0.548184 0.724363 0.088 Uiso 1 1 calc R U . . .
C49 C 0.5231(4) 0.353(6) 0.7574(10) 0.076(5) Uani 1 1 d . . . . .
H49 H 0.506691 0.283263 0.736732 0.092 Uiso 1 1 calc R U . . .
C50 C 0.5259(4) 0.513(5) 0.8104(10) 0.069(5) Uani 1 1 d . . . . .
H50 H 0.511144 0.551627 0.824445 0.082 Uiso 1 1 calc R U . . .
C51 C 0.5444(4) 0.302(6) 0.7373(9) 0.070(5) Uani 1 1 d . . . . .
H51 H 0.542444 0.198694 0.701892 0.084 Uiso 1 1 calc R U . . .
C52 C 0.5502(4) 0.617(6) 0.8426(10) 0.073(6) Uani 1 1 d . . . . .
H52 H 0.551844 0.720515 0.877869 0.088 Uiso 1 1 calc R U . . .
C53 C 0.5692(4) 0.394(5) 0.7666(9) 0.068(5) Uani 1 1 d . . . . .
C54 C 0.5719(4) 0.561(5) 0.8204(10) 0.064(5) Uani 1 1 d . . . . .
C55 C 0.5947(4) 0.362(5) 0.7555(9) 0.066(5) Uani 1 1 d . . . . .
C56 C 0.6135(4) 0.533(5) 0.8050(8) 0.056(5) Uani 1 1 d . . . . .
C57 C 0.6389(4) 0.556(5) 0.8105(9) 0.063(5) Uani 1 1 d . . . . .
H57 H 0.644683 0.460876 0.780341 0.076 Uiso 1 1 calc R U . . .
C58 C 0.6598(3) 0.703(5) 0.8549(8) 0.066(5) Uani 1 1 d . . . . .
C59 C 0.6850(3) 0.694(6) 0.8447(9) 0.071(5) Uani 1 1 d . . . . .
H59 H 0.687536 0.610398 0.810406 0.085 Uiso 1 1 calc R U . . .
C60 C 0.6572(3) 0.849(6) 0.9065(9) 0.076(6) Uani 1 1 d . . . . .
H60 H 0.640660 0.869879 0.913940 0.091 Uiso 1 1 calc R U . . .
C61 C 0.7063(4) 0.812(7) 0.8861(9) 0.085(7) Uani 1 1 d . . . . .
H61 H 0.723054 0.792691 0.880111 0.102 Uiso 1 1 calc R U . . .
C62 C 0.6781(4) 0.958(5) 0.9447(10) 0.072(6) Uani 1 1 d . . . . .
H62 H 0.675857 1.041254 0.979353 0.086 Uiso 1 1 calc R U . . .
C63 C 0.7027(4) 0.953(5) 0.9349(9) 0.067(5) Uani 1 1 d . . . . .
C64 C 0.7254(4) 1.092(7) 0.9773(10) 0.082(6) Uani 1 1 d . . . . .
H64 H 0.741604 1.085126 0.968122 0.099 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 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(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
C6 N1 C8 113.1(16) . . ?
C6 N1 H1A 123.4 . . ?
C8 N1 H1A 123.4 . . ?
C24 N2 C22 105.6(15) . . ?
C24 N2 H2A 127.2 . . ?
C22 N2 H2A 127.2 . . ?
C38 N3 C40 109.6(15) . . ?
C38 N3 H3A 125.2 . . ?
C40 N3 H3A 125.2 . . ?
C54 N4 C56 111.3(16) . . ?
C54 N4 H4A 124.3 . . ?
C56 N4 H4A 124.3 . . ?
C3 C1 C2 116.0(19) . . ?
C3 C1 H1 122.0 . . ?
C2 C1 H1 122.0 . . ?
C4 C2 C1 122(2) . . ?
C4 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C1 C3 C5 125(2) . . ?
C1 C3 H3 117.7 . . ?
C5 C3 H3 117.7 . . ?
C2 C4 C6 121(2) . . ?
C2 C4 H4 119.4 . . ?
C6 C4 H4 119.4 . . ?
C3 C5 C7 137.6(19) . . ?
C3 C5 C6 117.3(16) . . ?
C7 C5 C6 105.0(15) . . ?
N1 C6 C4 132(2) . . ?
N1 C6 C5 108.6(16) . . ?
C4 C6 C5 119.2(18) . . ?
O1 C7 C5 126.1(17) . . ?
O1 C7 C8 124.0(16) . . ?
C5 C7 C8 109.9(18) . . ?
C9 C8 N1 131.6(19) . . ?
C9 C8 C7 125(2) . . ?
N1 C8 C7 103.3(15) . . ?
C8 C9 C10 136.1(19) . . ?
C8 C9 H9 112.0 . . ?
C10 C9 H9 112.0 . . ?
C11 C10 C9 121(2) . . ?
C11 C10 C12 115.9(19) . . ?
C9 C10 C12 122.4(16) . . ?
C10 C11 C13 124(2) . . ?
C10 C11 H11 117.9 . . ?
C13 C11 H11 117.9 . . ?
C14 C12 C10 119.5(17) . . ?
C14 C12 H12 120.3 . . ?
C10 C12 H12 120.3 . . ?
C11 C13 C15 118.5(17) . . ?
C11 C13 H13 120.7 . . ?
C15 C13 H13 120.7 . . ?
C15 C14 C12 124(2) . . ?
C15 C14 H14 117.9 . . ?
C12 C14 H14 117.9 . . ?
C14 C15 C16 127(2) . . ?
C14 C15 C13 117.3(18) . . ?
C16 C15 C13 115.5(19) . . ?
O2 C16 C15 122(2) . . ?
O2 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C19 C17 C18 120.0(19) . . ?
C19 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C20 124(2) . . ?
C17 C18 H18 117.9 . . ?
C20 C18 H18 117.9 . . ?
C17 C19 C21 118(2) . . ?
C17 C19 H19 121.2 . . ?
C21 C19 H19 121.2 . . ?
C18 C20 C22 114(2) . . ?
C18 C20 H20 123.2 . . ?
C22 C20 H20 123.2 . . ?
C22 C21 C19 122.6(19) . . ?
C22 C21 C23 107.0(17) . . ?
C19 C21 C23 130.4(18) . . ?
C21 C22 N2 113.8(18) . . ?
C21 C22 C20 121.8(19) . . ?
N2 C22 C20 124(2) . . ?
O3 C23 C24 127.6(18) . . ?
O3 C23 C21 129.3(18) . . ?
C24 C23 C21 103.2(16) . . ?
N2 C24 C25 129.4(18) . . ?
N2 C24 C23 110.2(16) . . ?
C25 C24 C23 120.3(18) . . ?
C24 C25 C26 133.8(19) . . ?
C24 C25 H25 113.1 . . ?
C26 C25 H25 113.1 . . ?
C27 C26 C28 116.7(18) . . ?
C27 C26 C25 119.1(17) . . ?
C28 C26 C25 124.2(17) . . ?
C26 C27 C29 121(2) . . ?
C26 C27 H27 119.7 . . ?
C29 C27 H27 119.7 . . ?
C30 C28 C26 123.3(19) . . ?
C30 C28 H28 118.4 . . ?
C26 C28 H28 118.4 . . ?
C31 C29 C27 121.9(17) . . ?
C31 C29 H29 119.1 . . ?
C27 C29 H29 119.1 . . ?
C28 C30 C31 118.6(18) . . ?
C28 C30 H30 120.7 . . ?
C31 C30 H30 120.7 . . ?
C29 C31 C30 118.8(16) . . ?
C29 C31 C32 119.3(17) . . ?
C30 C31 C32 121.8(19) . . ?
O4 C32 C31 126(2) . . ?
O4 C32 H32 116.8 . . ?
C31 C32 H32 116.8 . . ?
C35 C33 C34 117.0(19) . . ?
C35 C33 H33 121.5 . . ?
C34 C33 H33 121.5 . . ?
C36 C34 C33 125.1(18) . . ?
C36 C34 H34 117.5 . . ?
C33 C34 H34 117.5 . . ?
C33 C35 C37 123(2) . . ?
C33 C35 H35 118.7 . . ?
C37 C35 H35 118.7 . . ?
C34 C36 C38 113.8(19) . . ?
C34 C36 H36 123.1 . . ?
C38 C36 H36 123.1 . . ?
C38 C37 C35 118.2(19) . . ?
C38 C37 C39 107.6(16) . . ?
C35 C37 C39 134(2) . . ?
N3 C38 C37 110.5(16) . . ?
N3 C38 C36 126.3(17) . . ?
C37 C38 C36 123.1(16) . . ?
O5 C39 C37 129(2) . . ?
O5 C39 C40 124.2(18) . . ?
C37 C39 C40 106.4(17) . . ?
C41 C40 N3 128.4(18) . . ?
C41 C40 C39 125.8(19) . . ?
N3 C40 C39 105.8(15) . . ?
C40 C41 C42 132.5(19) . . ?
C40 C41 H41 113.7 . . ?
C42 C41 H41 113.7 . . ?
C44 C42 C43 117.0(18) . . ?
C44 C42 C41 126.7(16) . . ?
C43 C42 C41 116.3(18) . . ?
C45 C43 C42 122(2) . . ?
C45 C43 H43 119.1 . . ?
C42 C43 H43 119.1 . . ?
C46 C44 C42 122.4(16) . . ?
C46 C44 H44 118.8 . . ?
C42 C44 H44 118.8 . . ?
C43 C45 C47 118.5(19) . . ?
C43 C45 H45 120.8 . . ?
C47 C45 H45 120.8 . . ?
C44 C46 C47 121.4(19) . . ?
C44 C46 H46 119.3 . . ?
C47 C46 H46 119.3 . . ?
C46 C47 C45 118.6(19) . . ?
C46 C47 C48 122(2) . . ?
C45 C47 C48 119.3(17) . . ?
O6 C48 C47 126(2) . . ?
O6 C48 H48 116.8 . . ?
C47 C48 H48 116.8 . . ?
C51 C49 C50 118.4(19) . . ?
C51 C49 H49 120.8 . . ?
C50 C49 H49 120.8 . . ?
C52 C50 C49 122.1(19) . . ?
C52 C50 H50 118.9 . . ?
C49 C50 H50 118.9 . . ?
C49 C51 C53 123(2) . . ?
C49 C51 H51 118.4 . . ?
C53 C51 H51 118.4 . . ?
C54 C52 C50 118(2) . . ?
C54 C52 H52 121.1 . . ?
C50 C52 H52 121.1 . . ?
C51 C53 C54 118.0(19) . . ?
C51 C53 C55 134(2) . . ?
C54 C53 C55 108.0(17) . . ?
N4 C54 C52 130(2) . . ?
N4 C54 C53 109.3(16) . . ?
C52 C54 C53 120.4(19) . . ?
O7 C55 C53 130.4(19) . . ?
O7 C55 C56 123.2(18) . . ?
C53 C55 C56 106.4(17) . . ?
C57 C56 N4 130.2(18) . . ?
C57 C56 C55 124.9(18) . . ?
N4 C56 C55 104.8(15) . . ?
C56 C57 C58 132.5(19) . . ?
C56 C57 H57 113.8 . . ?
C58 C57 H57 113.8 . . ?
C59 C58 C60 117.1(16) . . ?
C59 C58 C57 116.3(18) . . ?
C60 C58 C57 126.6(17) . . ?
C61 C59 C58 119.9(19) . . ?
C61 C59 H59 120.0 . . ?
C58 C59 H59 120.0 . . ?
C62 C60 C58 120.7(18) . . ?
C62 C60 H60 119.7 . . ?
C58 C60 H60 119.7 . . ?
C63 C61 C59 120.7(19) . . ?
C63 C61 H61 119.6 . . ?
C59 C61 H61 119.6 . . ?
C60 C62 C63 122(2) . . ?
C60 C62 H62 118.8 . . ?
C63 C62 H62 118.8 . . ?
C61 C63 C62 118.9(19) . . ?
C61 C63 C64 120(2) . . ?
C62 C63 C64 121(2) . . ?
O8 C64 C63 125(2) . . ?
O8 C64 H64 117.3 . . ?
C63 C64 H64 117.3 . . ?
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
O1 C7 1.29(2) . ?
O2 C16 1.23(3) . ?
O3 C23 1.23(2) . ?
O4 C32 1.18(3) . ?
O5 C39 1.25(2) . ?
O6 C48 1.22(3) . ?
O7 C55 1.24(2) . ?
O8 C64 1.21(3) . ?
N1 C6 1.35(2) . ?
N1 C8 1.39(2) . ?
N1 H1A 0.8600 . ?
N2 C24 1.38(2) . ?
N2 C22 1.42(2) . ?
N2 H2A 0.8600 . ?
N3 C38 1.37(2) . ?
N3 C40 1.42(2) . ?
N3 H3A 0.8600 . ?
N4 C54 1.37(2) . ?
N4 C56 1.42(2) . ?
N4 H4A 0.8600 . ?
C1 C3 1.33(3) . ?
C1 C2 1.47(3) . ?
C1 H1 0.9300 . ?
C2 C4 1.33(3) . ?
C2 H2 0.9300 . ?
C3 C5 1.39(2) . ?
C3 H3 0.9300 . ?
C4 C6 1.37(3) . ?
C4 H4 0.9300 . ?
C5 C7 1.41(2) . ?
C5 C6 1.45(3) . ?
C7 C8 1.47(3) . ?
C8 C9 1.33(2) . ?
C9 C10 1.44(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.33(3) . ?
C10 C12 1.45(3) . ?
C11 C13 1.40(3) . ?
C11 H11 0.9300 . ?
C12 C14 1.36(2) . ?
C12 H12 0.9300 . ?
C13 C15 1.43(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.33(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.42(3) . ?
C16 H16 0.9300 . ?
C17 C19 1.36(3) . ?
C17 C18 1.38(3) . ?
C17 H17 0.9300 . ?
C18 C20 1.40(3) . ?
C18 H18 0.9300 . ?
C19 C21 1.41(3) . ?
C19 H19 0.9300 . ?
C20 C22 1.44(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.33(3) . ?
C21 C23 1.49(3) . ?
C23 C24 1.48(3) . ?
C24 C25 1.39(3) . ?
C25 C26 1.47(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.37(3) . ?
C26 C28 1.40(3) . ?
C27 C29 1.38(3) . ?
C27 H27 0.9300 . ?
C28 C30 1.35(3) . ?
C28 H28 0.9300 . ?
C29 C31 1.35(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.40(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.46(3) . ?
C32 H32 0.9300 . ?
C33 C35 1.34(3) . ?
C33 C34 1.41(3) . ?
C33 H33 0.9300 . ?
C34 C36 1.39(3) . ?
C34 H34 0.9300 . ?
C35 C37 1.39(3) . ?
C35 H35 0.9300 . ?
C36 C38 1.41(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.39(3) . ?
C37 C39 1.44(3) . ?
C39 C40 1.47(3) . ?
C40 C41 1.36(2) . ?
C41 C42 1.44(3) . ?
C41 H41 0.9300 . ?
C42 C44 1.38(2) . ?
C42 C43 1.42(3) . ?
C43 C45 1.39(3) . ?
C43 H43 0.9300 . ?
C44 C46 1.35(2) . ?
C44 H44 0.9300 . ?
C45 C47 1.42(3) . ?
C45 H45 0.9300 . ?
C46 C47 1.39(2) . ?
C46 H46 0.9300 . ?
C47 C48 1.44(3) . ?
C48 H48 0.9300 . ?
C49 C51 1.34(3) . ?
C49 C50 1.40(3) . ?
C49 H49 0.9300 . ?
C50 C52 1.39(3) . ?
C50 H50 0.9300 . ?
C51 C53 1.38(3) . ?
C51 H51 0.9300 . ?
C52 C54 1.38(3) . ?
C52 H52 0.9300 . ?
C53 C54 1.43(3) . ?
C53 C55 1.43(3) . ?
C55 C56 1.52(3) . ?
C56 C57 1.31(3) . ?
C57 C58 1.47(3) . ?
C57 H57 0.9300 . ?
C58 C59 1.40(2) . ?
C58 C60 1.41(3) . ?
C59 C61 1.39(3) . ?
C59 H59 0.9300 . ?
C60 C62 1.33(3) . ?
C60 H60 0.9300 . ?
C61 C63 1.35(3) . ?
C61 H61 0.9300 . ?
C62 C63 1.37(3) . ?
C62 H62 0.9300 . ?
C63 C64 1.48(3) . ?
C64 H64 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O3 . . . 2.91(2) 0.860 2.127 151.9 no
N2 H2A O1 . . 2_565 2.87(2) 0.860 2.108 147.9 no
N3 H3A O7 . . . 2.96(2) 0.860 2.270 137.3 no
N4 H4A O5 . . 2_565 2.93(2) 0.860 2.148 150.5 no
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
C3 C1 C2 C4 1(3) . . . . ?
C2 C1 C3 C5 1(3) . . . . ?
C1 C2 C4 C6 -2(4) . . . . ?
C1 C3 C5 C7 -179(2) . . . . ?
C1 C3 C5 C6 -2(2) . . . . ?
C8 N1 C6 C4 -179.6(19) . . . . ?
C8 N1 C6 C5 -2(2) . . . . ?
C2 C4 C6 N1 177(2) . . . . ?
C2 C4 C6 C5 0(3) . . . . ?
C3 C5 C6 N1 -175.7(14) . . . . ?
C7 C5 C6 N1 2.2(19) . . . . ?
C3 C5 C6 C4 2(2) . . . . ?
C7 C5 C6 C4 179.9(18) . . . . ?
C3 C5 C7 O1 -4(4) . . . . ?
C6 C5 C7 O1 178.8(19) . . . . ?
C3 C5 C7 C8 175.8(17) . . . . ?
C6 C5 C7 C8 -1.4(19) . . . . ?
C6 N1 C8 C9 -180.0(16) . . . . ?
C6 N1 C8 C7 1.2(19) . . . . ?
O1 C7 C8 C9 1(3) . . . . ?
C5 C7 C8 C9 -178.7(15) . . . . ?
O1 C7 C8 N1 180.0(19) . . . . ?
C5 C7 C8 N1 0.2(19) . . . . ?
N1 C8 C9 C10 3(3) . . . . ?
C7 C8 C9 C10 -178.6(18) . . . . ?
C8 C9 C10 C11 -179.7(18) . . . . ?
C8 C9 C10 C12 -5(3) . . . . ?
C9 C10 C11 C13 -179.3(17) . . . . ?
C12 C10 C11 C13 5(2) . . . . ?
C11 C10 C12 C14 -5(3) . . . . ?
C9 C10 C12 C14 -180.0(16) . . . . ?
C10 C11 C13 C15 -6(3) . . . . ?
C10 C12 C14 C15 5(3) . . . . ?
C12 C14 C15 C16 179(2) . . . . ?
C12 C14 C15 C13 -5(3) . . . . ?
C11 C13 C15 C14 5(3) . . . . ?
C11 C13 C15 C16 -178.8(17) . . . . ?
C14 C15 C16 O2 -6(3) . . . . ?
C13 C15 C16 O2 178(2) . . . . ?
C19 C17 C18 C20 0(4) . . . . ?
C18 C17 C19 C21 3(3) . . . . ?
C17 C18 C20 C22 -4(3) . . . . ?
C17 C19 C21 C22 -1(3) . . . . ?
C17 C19 C21 C23 177(2) . . . . ?
C19 C21 C22 N2 -177.7(17) . . . . ?
C23 C21 C22 N2 4(2) . . . . ?
C19 C21 C22 C20 -4(3) . . . . ?
C23 C21 C22 C20 177.5(16) . . . . ?
C24 N2 C22 C21 -5(2) . . . . ?
C24 N2 C22 C20 -179.0(18) . . . . ?
C18 C20 C22 C21 6(3) . . . . ?
C18 C20 C22 N2 179.4(18) . . . . ?
C22 C21 C23 O3 180(2) . . . . ?
C19 C21 C23 O3 1(3) . . . . ?
C22 C21 C23 C24 -0.6(19) . . . . ?
C19 C21 C23 C24 -179(2) . . . . ?
C22 N2 C24 C25 -177(2) . . . . ?
C22 N2 C24 C23 4.7(19) . . . . ?
O3 C23 C24 N2 177(2) . . . . ?
C21 C23 C24 N2 -2.7(19) . . . . ?
O3 C23 C24 C25 -1(3) . . . . ?
C21 C23 C24 C25 178.7(18) . . . . ?
N2 C24 C25 C26 2(4) . . . . ?
C23 C24 C25 C26 -180(2) . . . . ?
C24 C25 C26 C27 -167(2) . . . . ?
C24 C25 C26 C28 12(4) . . . . ?
C28 C26 C27 C29 0(3) . . . . ?
C25 C26 C27 C29 -180.0(19) . . . . ?
C27 C26 C28 C30 -1(3) . . . . ?
C25 C26 C28 C30 180(2) . . . . ?
C26 C27 C29 C31 -1(3) . . . . ?
C26 C28 C30 C31 2(3) . . . . ?
C27 C29 C31 C30 2(3) . . . . ?
C27 C29 C31 C32 179.4(19) . . . . ?
C28 C30 C31 C29 -3(3) . . . . ?
C28 C30 C31 C32 -180(2) . . . . ?
C29 C31 C32 O4 179(2) . . . . ?
C30 C31 C32 O4 -4(4) . . . . ?
C35 C33 C34 C36 0(4) . . . . ?
C34 C33 C35 C37 2(3) . . . . ?
C33 C34 C36 C38 0(3) . . . . ?
C33 C35 C37 C38 -5(3) . . . . ?
C33 C35 C37 C39 -177(2) . . . . ?
C40 N3 C38 C37 3(2) . . . . ?
C40 N3 C38 C36 -179.8(19) . . . . ?
C35 C37 C38 N3 -177.7(17) . . . . ?
C39 C37 C38 N3 -4(2) . . . . ?
C35 C37 C38 C36 5(3) . . . . ?
C39 C37 C38 C36 179.6(18) . . . . ?
C34 C36 C38 N3 -179.2(18) . . . . ?
C34 C36 C38 C37 -3(3) . . . . ?
C38 C37 C39 O5 -179.5(19) . . . . ?
C35 C37 C39 O5 -7(4) . . . . ?
C38 C37 C39 C40 2(2) . . . . ?
C35 C37 C39 C40 175(2) . . . . ?
C38 N3 C40 C41 -178.9(19) . . . . ?
C38 N3 C40 C39 -2(2) . . . . ?
O5 C39 C40 C41 -2(3) . . . . ?
C37 C39 C40 C41 176.8(18) . . . . ?
O5 C39 C40 N3 -178.6(17) . . . . ?
C37 C39 C40 N3 0(2) . . . . ?
N3 C40 C41 C42 2(3) . . . . ?
C39 C40 C41 C42 -174.0(19) . . . . ?
C40 C41 C42 C44 5(3) . . . . ?
C40 C41 C42 C43 -175(2) . . . . ?
C44 C42 C43 C45 5(3) . . . . ?
C41 C42 C43 C45 -175.5(18) . . . . ?
C43 C42 C44 C46 -6(3) . . . . ?
C41 C42 C44 C46 174(2) . . . . ?
C42 C43 C45 C47 -3(3) . . . . ?
C42 C44 C46 C47 6(3) . . . . ?
C44 C46 C47 C45 -4(3) . . . . ?
C44 C46 C47 C48 178.8(18) . . . . ?
C43 C45 C47 C46 2(3) . . . . ?
C43 C45 C47 C48 179.7(18) . . . . ?
C46 C47 C48 O6 -2(3) . . . . ?
C45 C47 C48 O6 -180(2) . . . . ?
C51 C49 C50 C52 -1(3) . . . . ?
C50 C49 C51 C53 1(3) . . . . ?
C49 C50 C52 C54 1(3) . . . . ?
C49 C51 C53 C54 -2(3) . . . . ?
C49 C51 C53 C55 178(2) . . . . ?
C56 N4 C54 C52 -180(2) . . . . ?
C56 N4 C54 C53 2(2) . . . . ?
C50 C52 C54 N4 -179(2) . . . . ?
C50 C52 C54 C53 -1(3) . . . . ?
C51 C53 C54 N4 -180.0(17) . . . . ?
C55 C53 C54 N4 0(2) . . . . ?
C51 C53 C54 C52 2(3) . . . . ?
C55 C53 C54 C52 -178.3(18) . . . . ?
C51 C53 C55 O7 0(4) . . . . ?
C54 C53 C55 O7 180(2) . . . . ?
C51 C53 C55 C56 178(2) . . . . ?
C54 C53 C55 C56 -2(2) . . . . ?
C54 N4 C56 C57 -179.7(18) . . . . ?
C54 N4 C56 C55 -4(2) . . . . ?
O7 C55 C56 C57 -2(3) . . . . ?
C53 C55 C56 C57 179.8(17) . . . . ?
O7 C55 C56 N4 -178.4(19) . . . . ?
C53 C55 C56 N4 3(2) . . . . ?
N4 C56 C57 C58 -3(3) . . . . ?
C55 C56 C57 C58 -179(2) . . . . ?
C56 C57 C58 C59 -177.1(19) . . . . ?
C56 C57 C58 C60 3(4) . . . . ?
C60 C58 C59 C61 3(3) . . . . ?
C57 C58 C59 C61 -177(2) . . . . ?
C59 C58 C60 C62 -3(3) . . . . ?
C57 C58 C60 C62 177(2) . . . . ?
C58 C59 C61 C63 -4(4) . . . . ?
C58 C60 C62 C63 4(3) . . . . ?
C59 C61 C63 C62 4(4) . . . . ?
C59 C61 C63 C64 -177(2) . . . . ?
C60 C62 C63 C61 -4(3) . . . . ?
C60 C62 C63 C64 177(2) . . . . ?
C61 C63 C64 O8 -177(3) . . . . ?
C62 C63 C64 O8 1(4) . . . . ?
