##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_1746
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2004-08-31
_journal_date_accepted     2004-09-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue     10
_journal_page_first     o1725
_journal_page_last     o1727
_journal_paper_category     EO
_publ_contact_author_name     'Daqing Shi'
_publ_contact_author_address
;
Department of Chemistry
Xuzhou Normal University
Xuzhou 221116
People's Republic of China
;
_publ_contact_author_email     dqshi@263.net
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Ethyl 9-amino-7-(p-tolyl)-7H-pyrano[3,2-c]coumarin-8-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Jing Wang'
;
Department of Chemistry
Xuzhou Normal University
Xuzhou 221116
People's Republic of China
;
    'Daqing Shi'
;
Department of Chemistry
Xuzhou Normal University
Xuzhou 221116
People's Republic of China
The Key Laboratory of Biotechnology for
Medical Plants of Jiangsu Province
Xuzhou 221116
People's Republic of China
;
    'Xiangshan Wang'
;
Department of Chemistry
Xuzhou Normal University
Xuzhou 221116
People's Republic of China
The Key Laboratory of Biotechnology for
Medical Plants of Jiangsu Province
Xuzhou 221116
People's Republic of China
;
data_I
_chemical_name_systematic
;
Ethyl 9-amino-7-(p-tolyl)-7H-pyrano[3,2-c]coumarin-8-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H19 N O5'
_chemical_formula_sum     'C22 H19 N O5'
_chemical_formula_weight     377.38
_chemical_melting_point     '464-465'
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     15.239(2)
_cell_length_b     7.8500(10)
_cell_length_c     15.846(3)
_cell_angle_alpha     90.00
_cell_angle_beta     101.000(10)
_cell_angle_gamma     90.00
_cell_volume     1860.7(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     39
_cell_measurement_theta_min     3.11
_cell_measurement_theta_max     14.83
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.58
_exptl_crystal_size_mid     0.52
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.347
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     792
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens P4'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3918
_diffrn_reflns_av_R_equivalents     0.0135
_diffrn_reflns_av_sigmaI/netI     0.0384
_diffrn_reflns_theta_min     1.36
_diffrn_reflns_theta_max     25.25
_diffrn_reflns_theta_full     25.25
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     4.90
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3379
_reflns_number_gt     2173
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0660
_refine_ls_R_factor_gt     0.0397
_refine_ls_wR_factor_gt     0.0947
_refine_ls_wR_factor_ref     0.1012
_refine_ls_goodness_of_fit_ref     0.908
_refine_ls_restrained_S_all     0.909
_refine_ls_number_reflns     3379
_refine_ls_number_parameters     263
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.0538P)²] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.173
_refine_diff_density_min     -0.149
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.0124(9)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'XSCANS (Siemens, 1994)'
_computing_cell_refinement     'XSCANS'
_computing_data_reduction     'SHELXTL (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
loop_
    _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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    O1 0.64193(8) 0.19343(14) 0.21859(7) 0.0418(3) Uani d . 1 . . O
    O2 0.50048(7) 0.62681(16) 0.13568(8) 0.0463(3) Uani d . 1 . . O
    O3 0.59842(9) 0.78971(16) 0.21782(9) 0.0546(4) Uani d . 1 . . O
    O4 0.80705(9) 0.47615(17) 0.45982(8) 0.0561(4) Uani d . 1 . . O
    O5 0.80808(9) 0.18976(18) 0.46140(8) 0.0575(4) Uani d . 1 . . O
    N 0.72474(12) 0.0314(2) 0.31677(12) 0.0498(4) Uani d D 1 . . N
    C1 0.59831(10) 0.3425(2) 0.19417(10) 0.0347(4) Uani d . 1 . . C
    C2 0.51913(11) 0.3223(2) 0.12928(11) 0.0375(4) Uani d . 1 . . C
    C3 0.48594(12) 0.1657(2) 0.09449(12) 0.0476(5) Uani d . 1 . . C
    H3 0.5162 0.0653 0.1124 0.057 Uiso calc R 1 . . H
    C4 0.40829(13) 0.1611(3) 0.03366(13) 0.0570(6) Uani d . 1 . . C
    H4 0.3862 0.0574 0.0104 0.068 Uiso calc R 1 . . H
    C5 0.36301(13) 0.3104(3) 0.00695(13) 0.0581(6) Uani d . 1 . . C
    H5 0.3107 0.3055 -0.0343 0.070 Uiso calc R 1 . . H
    C6 0.39402(12) 0.4661(3) 0.04026(12) 0.0520(5) Uani d . 1 . . C
    H6 0.3636 0.5660 0.0218 0.062 Uiso calc R 1 . . H
    C7 0.47204(11) 0.4694(2) 0.10215(11) 0.0409(5) Uani d . 1 . . C
    C8 0.57810(11) 0.6455(2) 0.19591(11) 0.0398(4) Uani d . 1 . . C
    C9 0.62770(11) 0.4938(2) 0.22716(10) 0.0345(4) Uani d . 1 . . C
    C10 0.71228(11) 0.5094(2) 0.29399(11) 0.0359(4) Uani d . 1 . . C
    H10 0.7022 0.5937 0.3367 0.043 Uiso calc R 1 . . H
    C11 0.73056(10) 0.3380(2) 0.33873(11) 0.0366(4) Uani d . 1 . . C
    C12 0.70185(11) 0.1916(2) 0.29591(11) 0.0377(4) Uani d . 1 . . C
    C13 0.79247(11) 0.5667(2) 0.25616(11) 0.0347(4) Uani d . 1 . . C
    C14 0.80562(11) 0.5081(2) 0.17688(11) 0.0409(5) Uani d . 1 . . C
    H14 0.7624 0.4392 0.1441 0.049 Uiso calc R 1 . . H
    C15 0.88149(12) 0.5500(2) 0.14544(12) 0.0466(5) Uani d . 1 . . C
    H15 0.8883 0.5089 0.0920 0.056 Uiso calc R 1 . . H
    C16 0.94745(11) 0.6521(2) 0.19214(13) 0.0477(5) Uani d . 1 . . C
    C17 0.93370(12) 0.7113(2) 0.27057(13) 0.0520(5) Uani d . 1 . . C
    H17 0.9769 0.7806 0.3031 0.062 Uiso calc R 1 . . H
    C18 0.85807(11) 0.6713(2) 0.30227(12) 0.0446(5) Uani d . 1 . . C
    H18 0.8509 0.7148 0.3551 0.054 Uiso calc R 1 . . H
    C19 1.03096(13) 0.6967(3) 0.15922(15) 0.0724(7) Uani d . 1 . . C
    H19A 1.0289 0.6446 0.1041 0.087 Uiso calc PR 0.50 . . H
    H19B 1.0823 0.6558 0.1988 0.087 Uiso calc PR 0.50 . . H
    H19C 1.0349 0.8181 0.1538 0.087 Uiso calc PR 0.50 . . H
    H19D 1.0685 0.7678 0.2004 0.087 Uiso calc PR 0.50 . . H
    H19E 1.0151 0.7565 0.1056 0.087 Uiso calc PR 0.50 . . H
    H19F 1.0625 0.5942 0.1507 0.087 Uiso calc PR 0.50 . . H
    C20 0.78447(11) 0.3229(3) 0.42353(11) 0.0426(5) Uani d . 1 . . C
    C21 0.86360(16) 0.4768(3) 0.54441(13) 0.0740(7) Uani d . 1 . . C
    H21A 0.8995 0.5798 0.5512 0.089 Uiso calc R 1 . . H
    H21B 0.9040 0.3802 0.5494 0.089 Uiso calc R 1 . . H
    C22 0.81160(18) 0.4685(3) 0.61317(14) 0.0873(9) Uani d . 1 . . C
    H22A 0.7750 0.5684 0.6112 0.105 Uiso calc R 1 . . H
    H22B 0.8515 0.4625 0.6678 0.105 Uiso calc R 1 . . H
    H22C 0.7743 0.3690 0.6055 0.105 Uiso calc R 1 . . H
    H1A 0.7590(11) 0.017(2) 0.3679(8) 0.060(7) Uiso d D 1 . . H
    H1B 0.6907(12) -0.050(2) 0.2891(12) 0.076(8) Uiso d D 1 . . H
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    O1 C1 . 1.365(2) yes
    O1 C12 . 1.381(2) yes
    O2 C8 . 1.379(2) yes
    O2 C7 . 1.382(2) yes
    O3 C8 . 1.207(2) yes
    O4 C20 . 1.349(2) yes
    O4 C21 . 1.449(2) yes
    O5 C20 . 1.224(2) yes
    N C12 . 1.330(2) yes
    N H1A . 0.883(9) ?
    N H1B . 0.883(9) ?
    C1 C9 . 1.339(2) yes
    C1 C2 . 1.437(2) yes
    C2 C7 . 1.384(2) ?
    C2 C3 . 1.402(2) ?
    C3 C4 . 1.377(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.385(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.378(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.390(2) ?
    C6 H6 . 0.9300 ?
    C8 C9 . 1.447(2) yes
    C9 C10 . 1.509(2) yes
    C10 C11 . 1.521(2) yes
    C10 C13 . 1.528(2) ?
    C10 H10 . 0.9800 ?
    C11 C12 . 1.364(2) yes
    C11 C20 . 1.440(2) ?
    C13 C14 . 1.388(2) ?
    C13 C18 . 1.389(2) ?
    C14 C15 . 1.383(2) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.384(2) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.380(3) ?
    C16 C19 . 1.506(3) ?
    C17 C18 . 1.379(3) ?
    C17 H17 . 0.9300 ?
    C18 H18 . 0.9300 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C19 H19D . 0.9600 ?
    C19 H19E . 0.9600 ?
    C19 H19F . 0.9600 ?
    C21 C22 . 1.466(3) ?
    C21 H21A . 0.9700 ?
    C21 H21B . 0.9700 ?
    C22 H22A . 0.9600 ?
    C22 H22B . 0.9600 ?
    C22 H22C . 0.9600 ?
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
    C1 O1 C12 . . 117.65(13) yes
    C8 O2 C7 . . 121.75(14) yes
    C20 O4 C21 . . 117.13(16) yes
    C12 N H1A . . 115.4(13) ?
    C12 N H1B . . 117.2(14) ?
    H1A N H1B . . 124(2) ?
    C9 C1 O1 . . 122.75(15) yes
    C9 C1 C2 . . 123.37(16) yes
    O1 C1 C2 . . 113.88(15) yes
    C7 C2 C3 . . 118.87(16) ?
    C7 C2 C1 . . 116.40(16) ?
    C3 C2 C1 . . 124.70(17) ?
    C4 C3 C2 . . 119.71(19) ?
    C4 C3 H3 . . 120.1 ?
    C2 C3 H3 . . 120.1 ?
    C3 C4 C5 . . 120.2(2) ?
    C3 C4 H4 . . 119.9 ?
    C5 C4 H4 . . 119.9 ?
    C6 C5 C4 . . 121.26(18) ?
    C6 C5 H5 . . 119.4 ?
    C4 C5 H5 . . 119.4 ?
    C5 C6 C7 . . 118.1(2) ?
    C5 C6 H6 . . 120.9 ?
    C7 C6 H6 . . 120.9 ?
    O2 C7 C2 . . 121.38(15) yes
    O2 C7 C6 . . 116.85(17) yes
    C2 C7 C6 . . 121.77(18) ?
    O3 C8 O2 . . 115.99(16) yes
    O3 C8 C9 . . 125.82(16) yes
    O2 C8 C9 . . 118.19(16) yes
    C1 C9 C8 . . 118.84(16) yes
    C1 C9 C10 . . 121.54(15) yes
    C8 C9 C10 . . 119.60(15) yes
    C9 C10 C11 . . 108.14(13) yes
    C9 C10 C13 . . 112.86(13) ?
    C11 C10 C13 . . 110.74(13) ?
    C9 C10 H10 . . 108.3 ?
    C11 C10 H10 . . 108.3 ?
    C13 C10 H10 . . 108.3 ?
    C12 C11 C20 . . 117.82(16) ?
    C12 C11 C10 . . 120.04(15) ?
    C20 C11 C10 . . 121.92(16) ?
    N C12 C11 . . 128.99(17) yes
    N C12 O1 . . 109.15(16) yes
    C11 C12 O1 . . 121.84(16) yes
    C14 C13 C18 . . 117.28(16) ?
    C14 C13 C10 . . 121.47(15) ?
    C18 C13 C10 . . 121.13(16) ?
    C15 C14 C13 . . 121.50(16) ?
    C15 C14 H14 . . 119.2 ?
    C13 C14 H14 . . 119.2 ?
    C14 C15 C16 . . 121.10(18) ?
    C14 C15 H15 . . 119.4 ?
    C16 C15 H15 . . 119.4 ?
    C17 C16 C15 . . 117.19(17) ?
    C17 C16 C19 . . 121.14(18) ?
    C15 C16 C19 . . 121.7(2) ?
    C18 C17 C16 . . 122.18(17) ?
    C18 C17 H17 . . 118.9 ?
    C16 C17 H17 . . 118.9 ?
    C17 C18 C13 . . 120.73(18) ?
    C17 C18 H18 . . 119.6 ?
    C13 C18 H18 . . 119.6 ?
    C16 C19 H19A . . 109.5 ?
    C16 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C16 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C16 C19 H19D . . 109.5 ?
    H19A C19 H19D . . 141.1 ?
    H19B C19 H19D . . 56.3 ?
    H19C C19 H19D . . 56.3 ?
    C16 C19 H19E . . 109.5 ?
    H19A C19 H19E . . 56.3 ?
    H19B C19 H19E . . 141.1 ?
    H19C C19 H19E . . 56.3 ?
    H19D C19 H19E . . 109.5 ?
    C16 C19 H19F . . 109.5 ?
    H19A C19 H19F . . 56.3 ?
    H19B C19 H19F . . 56.3 ?
    H19C C19 H19F . . 141.1 ?
    H19D C19 H19F . . 109.5 ?
    H19E C19 H19F . . 109.5 ?
    O5 C20 O4 . . 121.66(16) ?
    O5 C20 C11 . . 126.13(18) ?
    O4 C20 C11 . . 112.21(16) ?
    O4 C21 C22 . . 112.2(2) ?
    O4 C21 H21A . . 109.2 ?
    C22 C21 H21A . . 109.2 ?
    O4 C21 H21B . . 109.2 ?
    C22 C21 H21B . . 109.2 ?
    H21A C21 H21B . . 107.9 ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
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
    C12 O1 C1 C9 . . . . 19.3(2) yes
    C12 O1 C1 C2 . . . . -161.54(14) yes
    C9 C1 C2 C7 . . . . -1.0(3) ?
    O1 C1 C2 C7 . . . . 179.88(14) ?
    C9 C1 C2 C3 . . . . -178.96(17) ?
    O1 C1 C2 C3 . . . . 1.9(2) ?
    C7 C2 C3 C4 . . . . 0.8(3) ?
    C1 C2 C3 C4 . . . . 178.73(17) ?
    C2 C3 C4 C5 . . . . -0.1(3) ?
    C3 C4 C5 C6 . . . . -0.1(3) ?
    C4 C5 C6 C7 . . . . -0.4(3) ?
    C8 O2 C7 C2 . . . . 1.7(2) yes
    C8 O2 C7 C6 . . . . -178.43(16) ?
    C3 C2 C7 O2 . . . . 178.48(15) ?
    C1 C2 C7 O2 . . . . 0.4(2) ?
    C3 C2 C7 C6 . . . . -1.3(3) ?
    C1 C2 C7 C6 . . . . -179.46(16) ?
    C5 C6 C7 O2 . . . . -178.68(16) ?
    C5 C6 C7 C2 . . . . 1.2(3) ?
    C7 O2 C8 O3 . . . . 176.84(15) yes
    C7 O2 C8 C9 . . . . -3.2(2) yes
    O1 C1 C9 C8 . . . . 178.61(15) yes
    C2 C1 C9 C8 . . . . -0.5(3) yes
    O1 C1 C9 C10 . . . . 0.3(3) yes
    C2 C1 C9 C10 . . . . -178.77(15) ?
    O3 C8 C9 C1 . . . . -177.49(18) ?
    O2 C8 C9 C1 . . . . 2.5(2) ?
    O3 C8 C9 C10 . . . . 0.8(3) ?
    O2 C8 C9 C10 . . . . -179.16(14) ?
    C1 C9 C10 C11 . . . . -22.8(2) ?
    C8 C9 C10 C11 . . . . 158.96(15) ?
    C1 C9 C10 C13 . . . . 100.09(18) ?
    C8 C9 C10 C13 . . . . -78.19(19) ?
    C9 C10 C11 C12 . . . . 28.4(2) yes
    C13 C10 C11 C12 . . . . -95.70(18) ?
    C9 C10 C11 C20 . . . . -157.01(15) yes
    C13 C10 C11 C20 . . . . 78.86(19) ?
    C20 C11 C12 N . . . . -8.7(3) yes
    C10 C11 C12 N . . . . 166.09(18) yes
    C20 C11 C12 O1 . . . . 172.70(15) yes
    C10 C11 C12 O1 . . . . -12.5(2) yes
    C1 O1 C12 N . . . . 168.35(14) yes
    C1 O1 C12 C11 . . . . -12.8(2) yes
    C9 C10 C13 C14 . . . . -38.7(2) ?
    C11 C10 C13 C14 . . . . 82.71(19) ?
    C9 C10 C13 C18 . . . . 145.38(16) ?
    C11 C10 C13 C18 . . . . -93.23(18) ?
    C18 C13 C14 C15 . . . . 0.9(3) ?
    C10 C13 C14 C15 . . . . -175.17(16) ?
    C13 C14 C15 C16 . . . . 0.1(3) ?
    C14 C15 C16 C17 . . . . -0.7(3) ?
    C14 C15 C16 C19 . . . . 179.17(18) ?
    C15 C16 C17 C18 . . . . 0.3(3) ?
    C19 C16 C17 C18 . . . . -179.58(18) ?
    C16 C17 C18 C13 . . . . 0.7(3) ?
    C14 C13 C18 C17 . . . . -1.3(3) ?
    C10 C13 C18 C17 . . . . 174.79(16) ?
    C21 O4 C20 O5 . . . . 2.4(3) ?
    C21 O4 C20 C11 . . . . -178.24(17) ?
    C12 C11 C20 O5 . . . . 0.6(3) ?
    C10 C11 C20 O5 . . . . -174.05(17) ?
    C12 C11 C20 O4 . . . . -178.69(15) ?
    C10 C11 C20 O4 . . . . 6.6(2) ?
    C20 O4 C21 C22 . . . . -88.2(2) ?
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
    N H1A O5 . 0.883(9) 2.042(16) 2.702(2) 131(2)
    N H1B O3 1_545 0.883(9) 2.058(10) 2.935(2) 171(2)
