#------------------------------------------------------------------------------
#$Date: 2024-05-06 06:20:48 +0200 (Mon 06 de May de 2024) $
#$Revision: 291722 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/30/2023070.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023070
loop_
_publ_author_name
'Metwally, Nadia H.'
'Elgemeie, Galal H.'
'Abd Al-Latif, El-Shimaa S M'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structure of
 2,4-di-amino-5-(4-hy-droxy-3-meth-oxy-phen-yl)-8,8-dimethyl-6-oxo-6,7,8,9-tetra-hydro-5H-chromeno[2,3-b]pyridine-3-carbo-nitrile-di-methyl-formamide-water
 (1/1/1).
;
_journal_coeditor_code           YZ2052
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              396
_journal_page_last               400
_journal_paper_doi               10.1107/S2056989024002615
_journal_volume                  80
_journal_year                    2024
_chemical_formula_moiety         'C22 H22 N4 O4, C3 H7 N O, H2 O'
_chemical_formula_sum            'C25 H31 N5 O6'
_chemical_formula_weight         497.55
_chemical_name_systematic
'2,4-Diamino-5-(4-hydroxy-3-methoxyphenyl)-8,8-dimethyl-6-oxo-6,7,8,9-tetrahydro-5H-chromeno[2,3-b]pyridine-3-carbonitrile--dimethylformamide--water (1/1/1)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 106.344(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9055(2)
_cell_length_b                   15.9600(3)
_cell_length_c                   16.4794(4)
_cell_measurement_reflns_used    76991
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      39.5630
_cell_measurement_theta_min      2.1720
_cell_volume                     2499.98(10)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
XP, Version 5.1 (Bruker, 1998)
;
_computing_publication_material
;
SHELXL2019/3 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2019/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            210685
_diffrn_reflns_theta_full        37.500
_diffrn_reflns_theta_max         37.784
_diffrn_reflns_theta_min         2.167
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         13416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0377
_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)+(0.0626P)²+0.4082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                11108
_reflns_number_total             13416
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2052.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2023070.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2023070
_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   0.981
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.41040(5) 0.66845(3) 0.58286(3) 0.01573(8) Uani d 1 . .
C C2 0.35681(6) 0.74408(3) 0.55675(4) 0.01397(8) Uani d 1 . .
N N2 0.21622(5) 0.75300(4) 0.54244(4) 0.01919(9) Uani d 1 . .
H H01 0.1683(13) 0.7091(8) 0.5522(8) 0.029(3) Uiso d 1 . .
H H02 0.1692(13) 0.7983(8) 0.5197(8) 0.032(3) Uiso d 1 . .
C C3 0.44457(6) 0.81052(3) 0.54550(3) 0.01332(8) Uani d 1 . .
C C4 0.59114(6) 0.79689(3) 0.55989(3) 0.01270(8) Uani d 1 . .
N N4 0.67486(5) 0.85813(3) 0.54512(4) 0.01630(9) Uani d 1 . .
H H03 0.7612(13) 0.8503(8) 0.5540(8) 0.030(3) Uiso d 1 . .
H H04 0.6425(14) 0.9076(8) 0.5296(8) 0.032(3) Uiso d 1 . .
C C4A 0.64624(5) 0.71688(3) 0.58823(3) 0.01254(8) Uani d 1 . .
C C5 0.80070(5) 0.69551(3) 0.60532(3) 0.01224(8) Uani d 1 . .
H H5 0.832899 0.714157 0.555889 0.015 Uiso calc 1 . .
C C5A 0.81825(6) 0.60167(3) 0.61409(3) 0.01306(8) Uani d 1 . .
C C6 0.94969(6) 0.56393(3) 0.60992(4) 0.01383(8) Uani d 1 . .
O O1 1.03852(5) 0.60592(3) 0.58804(3) 0.01802(8) Uani d 1 . .
C C7 0.97538(6) 0.47181(4) 0.63057(4) 0.01648(9) Uani d 1 . .
H H7A 1.075931 0.463992 0.661303 0.020 Uiso calc 1 . .
H H7B 0.956598 0.440073 0.576928 0.020 Uiso calc 1 . .
C C8 0.88588(6) 0.43440(4) 0.68387(4) 0.01705(9) Uani d 1 . .
C C9 0.73204(6) 0.45817(4) 0.64135(4) 0.01770(10) Uani d 1 . .
H H9A 0.698047 0.427626 0.587129 0.021 Uiso calc 1 . .
H H9B 0.673250 0.441184 0.678188 0.021 Uiso calc 1 . .
C C9A 0.71700(6) 0.55019(3) 0.62522(4) 0.01452(9) Uani d 1 . .
O O10 0.58553(5) 0.57747(3) 0.62246(3) 0.01756(8) Uani d 1 . .
C C10A 0.54867(6) 0.65861(3) 0.59701(4) 0.01403(9) Uani d 1 . .
C C11 0.38620(6) 0.89004(4) 0.51709(4) 0.01655(9) Uani d 1 . .
N N3 0.34038(7) 0.95535(4) 0.49419(5) 0.02514(12) Uani d 1 . .
C C12 0.93212(8) 0.46813(5) 0.77471(4) 0.02391(12) Uani d 1 . .
H H12A 1.026948 0.447741 0.803183 0.036 Uiso calc 1 . .
H H12B 0.866481 0.448682 0.805418 0.036 Uiso calc 1 . .
H H12C 0.932458 0.529524 0.773538 0.036 Uiso calc 1 . .
C C13 0.90238(8) 0.33896(4) 0.68645(6) 0.02501(13) Uani d 1 . .
H H13A 0.867471 0.316360 0.629044 0.038 Uiso calc 1 . .
H H13B 0.848265 0.314956 0.722263 0.038 Uiso calc 1 . .
H H13C 1.001952 0.324471 0.709689 0.038 Uiso calc 1 . .
C C21 0.89109(5) 0.73909(3) 0.68486(3) 0.01264(8) Uani d 1 . .
C C22 0.98270(6) 0.80413(3) 0.67880(3) 0.01367(8) Uani d 1 . .
H H22 0.991495 0.819834 0.624914 0.016 Uiso calc 1 . .
C C23 1.06120(6) 0.84614(4) 0.75094(4) 0.01489(9) Uani d 1 . .
O O2 1.15118(5) 0.91117(3) 0.75031(3) 0.01993(9) Uani d 1 . .
C C24 1.05186(6) 0.82200(4) 0.83128(4) 0.01673(9) Uani d 1 . .
O O3 1.12872(6) 0.85824(4) 0.90394(3) 0.02564(11) Uani d 1 . .
H H05 1.1648(14) 0.9072(8) 0.8971(8) 0.034(3) Uiso d 1 . .
C C25 0.96244(7) 0.75654(4) 0.83672(4) 0.01757(10) Uani d 1 . .
H H25 0.955884 0.739310 0.890663 0.021 Uiso calc 1 . .
C C26 0.88214(6) 0.71565(4) 0.76446(4) 0.01552(9) Uani d 1 . .
H H26 0.820851 0.671449 0.769635 0.019 Uiso calc 1 . .
C C27 1.16872(8) 0.93355(4) 0.67030(4) 0.02151(11) Uani d 1 . .
H H27A 1.077008 0.947598 0.631269 0.032 Uiso calc 1 . .
H H27B 1.209836 0.886314 0.647569 0.032 Uiso calc 1 . .
H H27C 1.231375 0.982140 0.676969 0.032 Uiso calc 1 . .
C C97 -0.12972(7) 0.83937(4) 0.40895(4) 0.02086(11) Uani d 1 . .
H H97 -0.220125 0.819639 0.409112 0.025 Uiso calc 1 . .
C C98 0.02521(8) 0.88437(5) 0.32596(5) 0.02539(13) Uani d 1 . .
H H98A 0.082462 0.904757 0.380990 0.038 Uiso calc 1 . .
H H98B 0.008664 0.930221 0.284779 0.038 Uiso calc 1 . .
H H98C 0.074841 0.838697 0.306776 0.038 Uiso calc 1 . .
O O98 -0.04221(6) 0.84926(4) 0.47838(3) 0.02704(11) Uani d 1 . .
N N99 -0.10846(6) 0.85392(4) 0.33387(3) 0.01883(9) Uani d 1 . .
C C99 -0.21966(8) 0.83914(6) 0.25620(5) 0.02841(14) Uani d 1 . .
H H99A -0.193276 0.792258 0.225408 0.043 Uiso calc 1 . .
H H99B -0.233445 0.889604 0.220932 0.043 Uiso calc 1 . .
H H99C -0.307232 0.825602 0.269909 0.043 Uiso calc 1 . .
O O99 1.23412(5) 1.01108(3) 0.92936(3) 0.02037(9) Uani d 1 . .
H H06 1.3078(14) 1.0356(8) 0.9237(8) 0.033(3) Uiso d 1 . .
H H07 1.1765(15) 1.0538(9) 0.9237(9) 0.039(3) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10A N1 C2 . . 117.21(5) y
N1 C2 N2 . . 116.49(5) ?
N1 C2 C3 . . 120.95(5) ?
N2 C2 C3 . . 122.56(5) ?
C2 N2 H01 . . 117.6(8) ?
C2 N2 H02 . . 123.6(8) ?
H01 N2 H02 . . 118.6(11) ?
C2 C3 C11 . . 120.33(5) ?
C2 C3 C4 . . 119.98(5) ?
C11 C3 C4 . . 119.65(5) ?
N4 C4 C4A . . 120.95(5) ?
N4 C4 C3 . . 120.71(5) ?
C4A C4 C3 . . 118.32(5) ?
C4 N4 H03 . . 120.8(9) ?
C4 N4 H04 . . 121.4(9) ?
H03 N4 H04 . . 117.7(12) ?
C10A C4A C4 . . 115.27(5) ?
C10A C4A C5 . . 122.02(5) ?
C4 C4A C5 . . 122.69(5) ?
C5A C5 C4A . . 108.92(4) ?
C5A C5 C21 . . 110.17(4) ?
C4A C5 C21 . . 111.95(4) ?
C5A C5 H5 . . 108.6 ?
C4A C5 H5 . . 108.6 ?
C21 C5 H5 . . 108.6 ?
C9A C5A C6 . . 117.67(5) ?
C9A C5A C5 . . 123.19(5) ?
C6 C5A C5 . . 119.14(5) ?
O1 C6 C5A . . 120.61(5) ?
O1 C6 C7 . . 120.18(5) ?
C5A C6 C7 . . 119.19(5) ?
C6 C7 C8 . . 114.77(5) ?
C6 C7 H7A . . 108.6 ?
C8 C7 H7A . . 108.6 ?
C6 C7 H7B . . 108.6 ?
C8 C7 H7B . . 108.6 ?
H7A C7 H7B . . 107.6 ?
C13 C8 C7 . . 109.19(5) ?
C13 C8 C12 . . 108.77(6) ?
C7 C8 C12 . . 111.11(5) ?
C13 C8 C9 . . 110.06(5) ?
C7 C8 C9 . . 107.58(5) ?
C12 C8 C9 . . 110.12(5) ?
C9A C9 C8 . . 111.17(5) ?
C9A C9 H9A . . 109.4 ?
C8 C9 H9A . . 109.4 ?
C9A C9 H9B . . 109.4 ?
C8 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
C5A C9A O10 . . 122.79(5) ?
C5A C9A C9 . . 125.66(5) ?
O10 C9A C9 . . 111.55(5) ?
C9A O10 C10A . . 118.66(5) ?
N1 C10A C4A . . 128.24(5) ?
N1 C10A O10 . . 109.59(5) ?
C4A C10A O10 . . 122.17(5) y
N3 C11 C3 . . 179.08(6) ?
C8 C12 H12A . . 109.5 ?
C8 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C8 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C8 C13 H13A . . 109.5 ?
C8 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C8 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C26 C21 C22 . . 118.77(5) ?
C26 C21 C5 . . 120.55(5) ?
C22 C21 C5 . . 120.68(5) ?
C23 C22 C21 . . 120.81(5) ?
C23 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
O2 C23 C22 . . 124.42(5) ?
O2 C23 C24 . . 115.46(5) ?
C22 C23 C24 . . 120.12(5) ?
C23 O2 C27 . . 116.52(5) ?
O3 C24 C25 . . 118.31(5) ?
O3 C24 C23 . . 123.06(6) ?
C25 C24 C23 . . 118.61(5) ?
C24 O3 H05 . . 114.5(9) ?
C24 C25 C26 . . 121.20(5) ?
C24 C25 H25 . . 119.4 ?
C26 C25 H25 . . 119.4 ?
C21 C26 C25 . . 120.48(5) ?
C21 C26 H26 . . 119.8 ?
C25 C26 H26 . . 119.8 ?
O2 C27 H27A . . 109.5 ?
O2 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
O2 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
O98 C97 N99 . . 125.77(7) ?
O98 C97 H97 . . 117.1 ?
N99 C97 H97 . . 117.1 ?
N99 C98 H98A . . 109.5 ?
N99 C98 H98B . . 109.5 ?
H98A C98 H98B . . 109.5 ?
N99 C98 H98C . . 109.5 ?
H98A C98 H98C . . 109.5 ?
H98B C98 H98C . . 109.5 ?
C97 N99 C98 . . 121.91(6) ?
C97 N99 C99 . . 120.70(6) ?
C98 N99 C99 . . 117.39(6) ?
N99 C99 H99A . . 109.5 ?
N99 C99 H99B . . 109.5 ?
H99A C99 H99B . . 109.5 ?
N99 C99 H99C . . 109.5 ?
H99A C99 H99C . . 109.5 ?
H99B C99 H99C . . 109.5 ?
H06 O99 H07 . . 100.5(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C10A . 1.3324(7) y
N1 C2 . 1.3399(7) y
C2 N2 . 1.3529(8) ?
C2 C3 . 1.4160(8) ?
N2 H01 . 0.886(13) ?
N2 H02 . 0.885(13) ?
C3 C11 . 1.4183(8) ?
C3 C4 . 1.4204(8) ?
C4 N4 . 1.3476(7) ?
C4 C4A . 1.4154(7) ?
N4 H03 . 0.836(13) ?
N4 H04 . 0.863(13) ?
C4A C10A . 1.3779(8) ?
C4A C5 . 1.5146(7) ?
C5 C5A . 1.5101(7) ?
C5 C21 . 1.5308(8) ?
C5 H5 . 1.0000 ?
C5A C9A . 1.3484(8) y
C5A C6 . 1.4535(8) ?
C6 O1 . 1.2377(7) ?
C6 C7 . 1.5145(8) ?
C7 C8 . 1.5337(9) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C13 . 1.5313(9) ?
C8 C12 . 1.5345(10) ?
C8 C9 . 1.5349(8) ?
C9 C9A . 1.4925(8) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C9A O10 . 1.3617(7) y
O10 C10A . 1.3783(7) y
C11 N3 . 1.1570(8) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C21 C26 . 1.3907(8) ?
C21 C22 . 1.4007(8) ?
C22 C23 . 1.3954(8) ?
C22 H22 . 0.9500 ?
C23 O2 . 1.3700(7) ?
C23 C24 . 1.4068(8) ?
O2 C27 . 1.4230(8) ?
C24 O3 . 1.3545(8) ?
C24 C25 . 1.3888(9) ?
O3 H05 . 0.879(14) ?
C25 C26 . 1.3941(8) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
C97 O98 . 1.2359(8) ?
C97 N99 . 1.3326(9) ?
C97 H97 . 0.9500 ?
C98 N99 . 1.4503(9) ?
C98 H98A . 0.9800 ?
C98 H98B . 0.9800 ?
C98 H98C . 0.9800 ?
N99 C99 . 1.4538(9) ?
C99 H99A . 0.9800 ?
C99 H99B . 0.9800 ?
C99 H99C . 0.9800 ?
O99 H06 . 0.856(14) ?
O99 H07 . 0.877(14) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H01 O1 1_455 0.886(13) 2.268(13) 3.1492(7) 173.6(11) yes
N2 H02 O98 . 0.885(13) 2.170(13) 2.9167(8) 141.8(11) yes
N4 H03 O98 1_655 0.836(13) 2.590(12) 3.2891(8) 142.0(11) yes
N4 H04 N3 3_676 0.863(13) 2.237(13) 3.0413(8) 154.9(12) yes
O3 H05 O99 . 0.879(14) 1.816(14) 2.6399(7) 155.2(12) yes
O99 H06 O1 2_756 0.856(14) 1.944(14) 2.7944(7) 172.0(13) yes
O99 H07 N1 2_656 0.877(14) 2.012(14) 2.8699(7) 165.5(13) yes
O99 H07 O10 2_656 0.877(14) 2.519(14) 3.2180(7) 137.2(11) yes
C22 H22 O98 1_655 0.95 2.39 3.3210(8) 166.7 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10A N1 C2 N2 . . . . 179.82(6) ?
C10A N1 C2 C3 . . . . -0.47(9) ?
N1 C2 C3 C11 . . . . 179.43(6) ?
N2 C2 C3 C11 . . . . -0.88(9) ?
N1 C2 C3 C4 . . . . 1.58(8) ?
N2 C2 C3 C4 . . . . -178.73(6) ?
C2 C3 C4 N4 . . . . 176.42(5) ?
C11 C3 C4 N4 . . . . -1.44(8) ?
C2 C3 C4 C4A . . . . -2.14(8) ?
C11 C3 C4 C4A . . . . 180.00(5) ?
N4 C4 C4A C10A . . . . -176.96(5) ?
C3 C4 C4A C10A . . . . 1.60(8) ?
N4 C4 C4A C5 . . . . 1.29(8) ?
C3 C4 C4A C5 . . . . 179.84(5) ?
C10A C4A C5 C5A . . . . 11.45(7) y
C4 C4A C5 C5A . . . . -166.67(5) ?
C10A C4A C5 C21 . . . . -110.63(6) ?
C4 C4A C5 C21 . . . . 71.24(6) ?
C4A C5 C5A C9A . . . . -14.61(7) y
C21 C5 C5A C9A . . . . 108.55(6) ?
C4A C5 C5A C6 . . . . 164.97(5) ?
C21 C5 C5A C6 . . . . -71.88(6) ?
C9A C5A C6 O1 . . . . 169.75(6) ?
C5 C5A C6 O1 . . . . -9.86(8) ?
C9A C5A C6 C7 . . . . -8.71(8) y
C5 C5A C6 C7 . . . . 171.68(5) ?
O1 C6 C7 C8 . . . . 160.51(6) ?
C5A C6 C7 C8 . . . . -21.02(8) y
C6 C7 C8 C13 . . . . 169.85(5) ?
C6 C7 C8 C12 . . . . -70.19(7) ?
C6 C7 C8 C9 . . . . 50.42(7) y
C13 C8 C9 C9A . . . . -170.71(6) ?
C7 C8 C9 C9A . . . . -51.84(7) y
C12 C8 C9 C9A . . . . 69.39(7) ?
C6 C5A C9A O10 . . . . -173.91(5) ?
C5 C5A C9A O10 . . . . 5.67(9) y
C6 C5A C9A C9 . . . . 5.77(9) y
C5 C5A C9A C9 . . . . -174.65(6) ?
C8 C9 C9A C5A . . . . 26.39(9) y
C8 C9 C9A O10 . . . . -153.90(5) ?
C5A C9A O10 C10A . . . . 8.25(9) y
C9 C9A O10 C10A . . . . -171.47(5) ?
C2 N1 C10A C4A . . . . -0.02(9) ?
C2 N1 C10A O10 . . . . -179.40(5) ?
C4 C4A C10A N1 . . . . -0.56(9) ?
C5 C4A C10A N1 . . . . -178.82(6) ?
C4 C4A C10A O10 . . . . 178.74(5) ?
C5 C4A C10A O10 . . . . 0.48(9) y
C9A O10 C10A N1 . . . . 168.16(5) ?
C9A O10 C10A C4A . . . . -11.26(9) y
C5A C5 C21 C26 . . . . -52.13(7) ?
C4A C5 C21 C26 . . . . 69.23(6) ?
C5A C5 C21 C22 . . . . 128.86(5) ?
C4A C5 C21 C22 . . . . -109.79(6) ?
C26 C21 C22 C23 . . . . -1.52(8) ?
C5 C21 C22 C23 . . . . 177.51(5) ?
C21 C22 C23 O2 . . . . -178.88(5) ?
C21 C22 C23 C24 . . . . 1.67(9) ?
C22 C23 O2 C27 . . . . -3.02(9) ?
C24 C23 O2 C27 . . . . 176.45(6) ?
O2 C23 C24 O3 . . . . -1.81(9) ?
C22 C23 C24 O3 . . . . 177.69(6) ?
O2 C23 C24 C25 . . . . 179.90(6) ?
C22 C23 C24 C25 . . . . -0.60(9) ?
O3 C24 C25 C26 . . . . -178.96(6) ?
C23 C24 C25 C26 . . . . -0.59(9) ?
C22 C21 C26 C25 . . . . 0.33(9) ?
C5 C21 C26 C25 . . . . -178.70(5) ?
C24 C25 C26 C21 . . . . 0.73(9) ?
O98 C97 N99 C98 . . . . -0.18(11) ?
O98 C97 N99 C99 . . . . 179.44(7) ?
