##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'by SHELXL-97'
_journal_date_recd_electronic     2013-03-25
_journal_date_accepted     2013-04-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      5
_journal_page_first     o764
_journal_page_last     o764
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813009161
_journal_coeditor_code     LD2099
_publ_contact_author_name     'Ms Xu Dan-Qian'
_publ_contact_author_address
;
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology
Zhejiang University of Technology
Hangzhou
310014
People's Republic of China
;
_publ_contact_author_email     'chrc@zjut.edu.cn'
_publ_contact_author_fax     '86 571 88320066'
_publ_contact_author_phone     '86 571 88320609'
_publ_section_title
;
2-[3-(2-Acetoxyphenyl)quinoxalin-2-yl]phenyl acetate
;
loop_
    _publ_author_name
    _publ_author_address
    'Dan-Fen Shen'
;
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology
Zhejiang University of Technology
Hangzhou
310014
People's Republic of China
;
    'Shao-Jie Lou'
;
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology
Zhejiang University of Technology
Hangzhou
310014
People's Republic of China
;
    'Dan-Qian Xu'
;
State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology
Zhejiang University of Technology
Hangzhou
310014
People's Republic of China
;
data_I
_chemical_name_systematic
;
2-[3-(2-Acetoxyphenyl)quinoxalin-2-yl]phenyl acetate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H18 N2 O4'
_chemical_formula_sum     'C24 H18 N2 O4'
_chemical_formula_iupac     'C24 H18 N2 O4'
_chemical_formula_weight     398.40
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 1 21/c 1'
_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     9.5723(5)
_cell_length_b     16.7309(8)
_cell_length_c     13.0555(6)
_cell_angle_alpha     90.00
_cell_angle_beta     92.929(2)
_cell_angle_gamma     90.00
_cell_volume     2088.15(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     11299
_cell_measurement_theta_min     3.1
_cell_measurement_theta_max     27.4
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'platelet'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.46
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.267
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     832
_exptl_absorpt_coefficient_mu     0.087
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.9592
_exptl_absorpt_correction_T_max     0.9827
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID/ZJUG'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.00
_diffrn_reflns_number     15632
_diffrn_reflns_av_R_equivalents     0.0431
_diffrn_reflns_av_sigmaI/netI     0.0342
_diffrn_reflns_theta_min     3.12
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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     3646
_reflns_number_gt     2553
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0683
_refine_ls_R_factor_gt     0.0452
_refine_ls_wR_factor_gt     0.0999
_refine_ls_wR_factor_ref     0.1173
_refine_ls_goodness_of_fit_ref     1.004
_refine_ls_restrained_S_all     1.004
_refine_ls_number_reflns     3646
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0450P)²+0.7545P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.173
_refine_diff_density_min     -0.197
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.045(2)
_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     'PROCESS-AUTO  (Rigaku, 2006)'
_computing_cell_refinement     'PROCESS-AUTO  (Rigaku, 2006)'
_computing_data_reduction     'CrystalStructure (Rigaku, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material     'WinGX (Farrugia, 2012)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.57616(19) 0.12138(11) 0.27152(13) 0.0401(4) Uani d . 1 1 . .
    C C2 0.7311(2) 0.02174(11) 0.31884(15) 0.0467(5) Uani d . 1 1 . .
    C C3 0.7625(3) -0.04950(13) 0.37296(19) 0.0678(6) Uani d . 1 1 . .
    H H3 0.6940 -0.0747 0.4093 0.081 Uiso calc R 1 1 . .
    C C4 0.8934(3) -0.08127(15) 0.3718(2) 0.0778(7) Uani d . 1 1 . .
    H H4 0.9141 -0.1280 0.4080 0.093 Uiso calc R 1 1 . .
    C C5 0.9964(3) -0.04432(15) 0.3169(2) 0.0783(7) Uani d . 1 1 . .
    H H5 1.0850 -0.0671 0.3166 0.094 Uiso calc R 1 1 . .
    C C6 0.9699(2) 0.02435(14) 0.2639(2) 0.0704(7) Uani d . 1 1 . .
    H H6 1.0394 0.0480 0.2270 0.085 Uiso calc R 1 1 . .
    C C7 0.8360(2) 0.05939(12) 0.26533(15) 0.0494(5) Uani d . 1 1 . .
    C C8 0.68513(19) 0.16210(11) 0.22108(14) 0.0429(5) Uani d . 1 1 . .
    C C9 0.43173(19) 0.15473(11) 0.27655(14) 0.0438(5) Uani d . 1 1 . .
    C C10 0.3759(2) 0.16739(13) 0.37183(17) 0.0586(6) Uani d . 1 1 . .
    H H10 0.4290 0.1545 0.4312 0.070 Uiso calc R 1 1 . .
    C C11 0.2436(3) 0.19857(15) 0.3797(2) 0.0714(7) Uani d . 1 1 . .
    H H11 0.2083 0.2068 0.4439 0.086 Uiso calc R 1 1 . .
    C C12 0.1641(2) 0.21744(15) 0.2926(2) 0.0731(7) Uani d . 1 1 . .
    H H12 0.0751 0.2389 0.2980 0.088 Uiso calc R 1 1 . .
    C C13 0.2152(2) 0.20474(14) 0.19734(19) 0.0628(6) Uani d . 1 1 . .
    H H13 0.1610 0.2171 0.1383 0.075 Uiso calc R 1 1 . .
    C C14 0.3478(2) 0.17335(12) 0.19050(15) 0.0473(5) Uani d . 1 1 . .
    C C15 0.3570(3) 0.09580(15) 0.04113(19) 0.0727(7) Uani d . 1 1 . .
    C C16 0.4121(3) 0.09362(19) -0.0632(2) 0.0940(9) Uani d . 1 1 . .
    H H16A 0.3871 0.0438 -0.0956 0.141 Uiso calc R 1 1 . .
    H H16B 0.5121 0.0987 -0.0581 0.141 Uiso calc R 1 1 . .
    H H16C 0.3727 0.1369 -0.1033 0.141 Uiso calc R 1 1 . .
    C C17 0.66704(19) 0.24376(11) 0.17661(15) 0.0432(5) Uani d . 1 1 . .
    C C18 0.6188(2) 0.30646(12) 0.23494(17) 0.0537(5) Uani d . 1 1 . .
    H H18 0.5930 0.2967 0.3015 0.064 Uiso calc R 1 1 . .
    C C19 0.6084(2) 0.38308(13) 0.19573(19) 0.0622(6) Uani d . 1 1 . .
    H H19 0.5755 0.4244 0.2357 0.075 Uiso calc R 1 1 . .
    C C20 0.6466(2) 0.39806(14) 0.09761(19) 0.0650(6) Uani d . 1 1 . .
    H H20 0.6390 0.4495 0.0710 0.078 Uiso calc R 1 1 . .
    C C21 0.6961(2) 0.33717(13) 0.03828(17) 0.0577(6) Uani d . 1 1 . .
    H H21 0.7231 0.3475 -0.0279 0.069 Uiso calc R 1 1 . .
    C C22 0.70544(19) 0.26088(11) 0.07788(15) 0.0448(5) Uani d . 1 1 . .
    C C23 0.8838(2) 0.19247(13) -0.00467(16) 0.0554(5) Uani d . 1 1 . .
    C C24 0.9139(3) 0.11638(17) -0.0569(2) 0.0940(9) Uani d . 1 1 . .
    H H24A 1.0092 0.1164 -0.0765 0.141 Uiso calc R 1 1 . .
    H H24B 0.8524 0.1108 -0.1169 0.141 Uiso calc R 1 1 . .
    H H24C 0.8997 0.0726 -0.0111 0.141 Uiso calc R 1 1 . .
    N N1 0.59936(17) 0.05326(9) 0.32027(12) 0.0467(4) Uani d . 1 1 . .
    N N2 0.81105(17) 0.13064(10) 0.21658(13) 0.0513(4) Uani d . 1 1 . .
    O O1 0.40006(15) 0.16132(9) 0.09276(10) 0.0569(4) Uani d . 1 1 . .
    O O2 0.2849(3) 0.04774(14) 0.0780(2) 0.1502(12) Uani d . 1 1 . .
    O O3 0.74576(14) 0.19711(8) 0.01622(10) 0.0536(4) Uani d . 1 1 . .
    O O4 0.96565(16) 0.24378(10) 0.01729(13) 0.0718(5) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    C1 N1 . 1.319(2) ?
    C1 C8 . 1.434(2) ?
    C1 C9 . 1.495(3) ?
    C2 N1 . 1.368(2) ?
    C2 C7 . 1.401(3) ?
    C2 C3 . 1.410(3) ?
    C3 C4 . 1.362(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.393(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.359(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.410(3) ?
    C6 H6 . 0.9300 ?
    C7 N2 . 1.367(2) ?
    C8 N2 . 1.319(2) ?
    C8 C17 . 1.491(3) ?
    C9 C14 . 1.383(3) ?
    C9 C10 . 1.395(3) ?
    C10 C11 . 1.378(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.372(4) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.376(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.381(3) ?
    C13 H13 . 0.9300 ?
    C14 O1 . 1.409(2) ?
    C15 O2 . 1.178(3) ?
    C15 O1 . 1.341(3) ?
    C15 C16 . 1.486(3) ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 C22 . 1.388(3) ?
    C17 C18 . 1.389(3) ?
    C18 C19 . 1.382(3) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.373(3) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.379(3) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.378(3) ?
    C21 H21 . 0.9300 ?
    C22 O3 . 1.403(2) ?
    C23 O4 . 1.188(2) ?
    C23 O3 . 1.365(2) ?
    C23 C24 . 1.479(3) ?
    C24 H24A . 0.9600 ?
    C24 H24B . 0.9600 ?
    C24 H24C . 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
    N1 C1 C8 . . 121.58(17) ?
    N1 C1 C9 . . 115.76(16) ?
    C8 C1 C9 . . 122.60(16) ?
    N1 C2 C7 . . 121.18(17) ?
    N1 C2 C3 . . 119.48(18) ?
    C7 C2 C3 . . 119.34(19) ?
    C4 C3 C2 . . 119.8(2) ?
    C4 C3 H3 . . 120.1 ?
    C2 C3 H3 . . 120.1 ?
    C3 C4 C5 . . 120.6(2) ?
    C3 C4 H4 . . 119.7 ?
    C5 C4 H4 . . 119.7 ?
    C6 C5 C4 . . 121.2(2) ?
    C6 C5 H5 . . 119.4 ?
    C4 C5 H5 . . 119.4 ?
    C5 C6 C7 . . 119.4(2) ?
    C5 C6 H6 . . 120.3 ?
    C7 C6 H6 . . 120.3 ?
    N2 C7 C2 . . 120.79(17) ?
    N2 C7 C6 . . 119.56(19) ?
    C2 C7 C6 . . 119.63(19) ?
    N2 C8 C1 . . 121.24(17) ?
    N2 C8 C17 . . 115.87(16) ?
    C1 C8 C17 . . 122.78(16) ?
    C14 C9 C10 . . 117.21(18) ?
    C14 C9 C1 . . 123.25(17) ?
    C10 C9 C1 . . 119.53(17) ?
    C11 C10 C9 . . 121.3(2) ?
    C11 C10 H10 . . 119.4 ?
    C9 C10 H10 . . 119.4 ?
    C12 C11 C10 . . 119.9(2) ?
    C12 C11 H11 . . 120.0 ?
    C10 C11 H11 . . 120.0 ?
    C11 C12 C13 . . 120.3(2) ?
    C11 C12 H12 . . 119.8 ?
    C13 C12 H12 . . 119.8 ?
    C12 C13 C14 . . 119.2(2) ?
    C12 C13 H13 . . 120.4 ?
    C14 C13 H13 . . 120.4 ?
    C13 C14 C9 . . 122.07(19) ?
    C13 C14 O1 . . 118.89(18) ?
    C9 C14 O1 . . 119.04(17) ?
    O2 C15 O1 . . 121.6(2) ?
    O2 C15 C16 . . 126.9(3) ?
    O1 C15 C16 . . 111.5(2) ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C22 C17 C18 . . 117.67(18) ?
    C22 C17 C8 . . 121.31(17) ?
    C18 C17 C8 . . 120.91(17) ?
    C19 C18 C17 . . 121.1(2) ?
    C19 C18 H18 . . 119.4 ?
    C17 C18 H18 . . 119.4 ?
    C20 C19 C18 . . 119.8(2) ?
    C20 C19 H19 . . 120.1 ?
    C18 C19 H19 . . 120.1 ?
    C19 C20 C21 . . 120.3(2) ?
    C19 C20 H20 . . 119.8 ?
    C21 C20 H20 . . 119.8 ?
    C22 C21 C20 . . 119.4(2) ?
    C22 C21 H21 . . 120.3 ?
    C20 C21 H21 . . 120.3 ?
    C21 C22 C17 . . 121.62(19) ?
    C21 C22 O3 . . 120.24(18) ?
    C17 C22 O3 . . 118.01(16) ?
    O4 C23 O3 . . 123.0(2) ?
    O4 C23 C24 . . 126.2(2) ?
    O3 C23 C24 . . 110.8(2) ?
    C23 C24 H24A . . 109.5 ?
    C23 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C23 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C1 N1 C2 . . 117.34(16) ?
    C8 N2 C7 . . 117.73(16) ?
    C15 O1 C14 . . 117.26(16) ?
    C23 O3 C22 . . 117.10(15) ?
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
    N1 C2 C3 C4 . . . . 179.9(2) ?
    C7 C2 C3 C4 . . . . -0.7(3) ?
    C2 C3 C4 C5 . . . . -0.5(4) ?
    C3 C4 C5 C6 . . . . 0.5(4) ?
    C4 C5 C6 C7 . . . . 0.7(4) ?
    N1 C2 C7 N2 . . . . 2.8(3) ?
    C3 C2 C7 N2 . . . . -176.6(2) ?
    N1 C2 C7 C6 . . . . -178.78(19) ?
    C3 C2 C7 C6 . . . . 1.8(3) ?
    C5 C6 C7 N2 . . . . 176.6(2) ?
    C5 C6 C7 C2 . . . . -1.9(4) ?
    N1 C1 C8 N2 . . . . 3.9(3) ?
    C9 C1 C8 N2 . . . . -178.99(17) ?
    N1 C1 C8 C17 . . . . -172.21(17) ?
    C9 C1 C8 C17 . . . . 4.9(3) ?
    N1 C1 C9 C14 . . . . -124.4(2) ?
    C8 C1 C9 C14 . . . . 58.4(3) ?
    N1 C1 C9 C10 . . . . 54.9(2) ?
    C8 C1 C9 C10 . . . . -122.4(2) ?
    C14 C9 C10 C11 . . . . -1.2(3) ?
    C1 C9 C10 C11 . . . . 179.5(2) ?
    C9 C10 C11 C12 . . . . 0.3(4) ?
    C10 C11 C12 C13 . . . . 0.6(4) ?
    C11 C12 C13 C14 . . . . -0.5(4) ?
    C12 C13 C14 C9 . . . . -0.5(3) ?
    C12 C13 C14 O1 . . . . -179.3(2) ?
    C10 C9 C14 C13 . . . . 1.3(3) ?
    C1 C9 C14 C13 . . . . -179.44(19) ?
    C10 C9 C14 O1 . . . . -179.88(17) ?
    C1 C9 C14 O1 . . . . -0.6(3) ?
    N2 C8 C17 C22 . . . . 52.2(3) ?
    C1 C8 C17 C22 . . . . -131.55(19) ?
    N2 C8 C17 C18 . . . . -124.0(2) ?
    C1 C8 C17 C18 . . . . 52.3(3) ?
    C22 C17 C18 C19 . . . . 0.5(3) ?
    C8 C17 C18 C19 . . . . 176.78(19) ?
    C17 C18 C19 C20 . . . . -0.2(3) ?
    C18 C19 C20 C21 . . . . -0.4(3) ?
    C19 C20 C21 C22 . . . . 0.8(3) ?
    C20 C21 C22 C17 . . . . -0.5(3) ?
    C20 C21 C22 O3 . . . . 175.29(18) ?
    C18 C17 C22 C21 . . . . -0.1(3) ?
    C8 C17 C22 C21 . . . . -176.41(18) ?
    C18 C17 C22 O3 . . . . -176.01(17) ?
    C8 C17 C22 O3 . . . . 7.7(3) ?
    C8 C1 N1 C2 . . . . -1.5(3) ?
    C9 C1 N1 C2 . . . . -178.85(16) ?
    C7 C2 N1 C1 . . . . -1.7(3) ?
    C3 C2 N1 C1 . . . . 177.72(19) ?
    C1 C8 N2 C7 . . . . -2.7(3) ?
    C17 C8 N2 C7 . . . . 173.69(17) ?
    C2 C7 N2 C8 . . . . -0.5(3) ?
    C6 C7 N2 C8 . . . . -178.93(19) ?
    O2 C15 O1 C14 . . . . -4.3(4) ?
    C16 C15 O1 C14 . . . . 176.0(2) ?
    C13 C14 O1 C15 . . . . -79.8(3) ?
    C9 C14 O1 C15 . . . . 101.3(2) ?
    O4 C23 O3 C22 . . . . -8.4(3) ?
    C24 C23 O3 C22 . . . . 171.6(2) ?
    C21 C22 O3 C23 . . . . 74.4(2) ?
    C17 C22 O3 C23 . . . . -109.70(19) ?
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
    C13 H13 O4 1_455 0.93 2.43 3.329(2) 163.5
