##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-09-05
_journal_date_accepted     2007-09-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     10
_journal_page_first     o4035
_journal_page_last     o4035
_journal_paper_category     QO
_journal_coeditor_code     HB2534
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    'Han, Jian-Rong'
;
College of Sciences
Hebei University of Science & Technology
Shijiazhuang 050018
P. R. China
;
_publ_contact_author_email     'han_jianrong@163.com, liu_shouxin@163.com'
_publ_contact_author_fax     '086(0311)87828831'
_publ_contact_author_phone     '086(0311)96707094'
_publ_section_title
;
(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro
-1H-pyrazol-4-ylimino)methyl]phenyl 4-chlorobenzoate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    "Han, Jian-Rong"
;
College of Sciences
Hebei University of Science and Technology
Shijiazhuang 050018
People's Republic of China
;
    "Zhen, Xiao-Li"
;
College of Sciences
Hebei University of Science and Technology
Shijiazhuang 050018
People's Republic of China
;
    "Tian, Xia"
;
College of Sciences
Hebei University of Science and Technology
Shijiazhuang 050018
People's Republic of China
;
    "Li, Fang"
;
College of Chemical and Pharmaceutical Engineering
Hebei University of Science and Technology
Shijiazhuang 050018
People's Republic of China
;
    "Liu, Shou-Xin"
;
College of Chemical and Pharmaceutical Engineering
Hebei University of Science and Technology
Shijiazhuang 050018
People's Republic of China
;
_chemical_name_systematic
;
 (E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro
 -1H-pyrazol-4-ylimino)methyl]phenyl 4-chlorobenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C25 H20 Cl N3 O3'
_chemical_formula_sum     'C25 H20 Cl N3 O3'
_chemical_formula_iupac     'C25 H20 Cl N3 O3'
_chemical_formula_weight     445.89
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     31.764(7)
_cell_length_b     6.7113(16)
_cell_length_c     25.605(6)
_cell_angle_alpha     90.00
_cell_angle_beta     126.165(3)
_cell_angle_gamma     90.00
_cell_volume     4406.7(18)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2545
_cell_measurement_theta_min     3.15
_cell_measurement_theta_max     24.21
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.344
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1856
_exptl_absorpt_coefficient_mu     0.206
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.921
_exptl_absorpt_correction_T_max     0.960
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10804
_diffrn_reflns_av_R_equivalents     0.0510
_diffrn_reflns_av_sigmaI/netI     0.0571
_diffrn_reflns_theta_min     1.59
_diffrn_reflns_theta_max     25.20
_diffrn_reflns_theta_full     25.20
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -38
_diffrn_reflns_limit_h_max     37
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     29
_diffrn_standards_number     0
_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 > 2σ(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     3962
_reflns_number_gt     2422
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0869
_refine_ls_R_factor_gt     0.0436
_refine_ls_wR_factor_gt     0.1017
_refine_ls_wR_factor_ref     0.1204
_refine_ls_goodness_of_fit_ref     1.029
_refine_ls_restrained_S_all     1.029
_refine_ls_number_reflns     3962
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0549P)²+0.4018P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.227
_refine_diff_density_min     -0.212
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.0009(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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997a)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997a)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material     'SHELXTL (Sheldrick, 1997b)'
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_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.02921(3) 0.85943(14) 0.32838(3) 0.0868(3) Uani d . 1 . .
    O O1 0.06375(6) 0.6862(2) 0.60622(7) 0.0559(5) Uani d . 1 . .
    O O2 0.10080(8) 0.9908(3) 0.62984(8) 0.0897(7) Uani d . 1 . .
    O O3 0.14117(6) 0.6064(2) 0.98425(7) 0.0527(4) Uani d . 1 . .
    N N1 0.14862(7) 0.3501(3) 0.88646(8) 0.0454(5) Uani d . 1 . .
    N N2 0.20831(7) 0.1617(3) 1.04555(8) 0.0450(5) Uani d . 1 . .
    N N3 0.18559(7) 0.3329(3) 1.05031(8) 0.0423(5) Uani d . 1 . .
    C C1 0.07274(9) 1.0228(4) 0.50268(11) 0.0637(7) Uani d . 1 . .
    H H1 0.0863 1.1358 0.5286 0.076 Uiso calc R 1 . .
    C C2 0.06193(9) 1.0265(5) 0.44201(12) 0.0655(7) Uani d . 1 . .
    H H2 0.0678 1.1410 0.4267 0.079 Uiso calc R 1 . .
    C C3 0.04222(8) 0.8573(4) 0.40467(10) 0.0548(7) Uani d . 1 . .
    C C4 0.03306(9) 0.6874(4) 0.42588(11) 0.0567(7) Uani d . 1 . .
    H H4 0.0200 0.5742 0.4000 0.068 Uiso calc R 1 . .
    C C5 0.04351(8) 0.6865(4) 0.48666(10) 0.0526(6) Uani d . 1 . .
    H H5 0.0369 0.5725 0.5013 0.063 Uiso calc R 1 . .
    C C6 0.06368(8) 0.8535(4) 0.52553(10) 0.0475(6) Uani d . 1 . .
    C C7 0.07797(9) 0.8564(4) 0.59202(11) 0.0547(7) Uani d . 1 . .
    C C8 0.07828(8) 0.6511(4) 0.66906(10) 0.0477(6) Uani d . 1 . .
    C C9 0.09811(9) 0.4660(4) 0.69396(10) 0.0545(6) Uani d . 1 . .
    H H9 0.1023 0.3739 0.6702 0.065 Uiso calc R 1 . .
    C C10 0.11186(9) 0.4166(4) 0.75437(11) 0.0541(6) Uani d . 1 . .
    H H10 0.1253 0.2907 0.7712 0.065 Uiso calc R 1 . .
    C C11 0.10592(8) 0.5522(4) 0.79049(10) 0.0470(6) Uani d . 1 . .
    C C12 0.08446(9) 0.7354(4) 0.76314(11) 0.0601(7) Uani d . 1 . .
    H H12 0.0790 0.8263 0.7860 0.072 Uiso calc R 1 . .
    C C13 0.07073(9) 0.7882(4) 0.70247(11) 0.0602(7) Uani d . 1 . .
    H H13 0.0568 0.9131 0.6850 0.072 Uiso calc R 1 . .
    C C14 0.12225(8) 0.5065(4) 0.85623(10) 0.0507(6) Uani d . 1 . .
    H H14 0.1132 0.5936 0.8763 0.061 Uiso calc R 1 . .
    C C15 0.16474(8) 0.3141(3) 0.94963(10) 0.0391(5) Uani d . 1 . .
    C C16 0.19226(8) 0.1468(3) 0.98340(10) 0.0422(5) Uani d . 1 . .
    C C17 0.16029(8) 0.4388(3) 0.99142(10) 0.0398(5) Uani d . 1 . .
    C C18 0.20356(9) -0.0335(4) 0.96011(11) 0.0579(7) Uani d . 1 . .
    H H18A 0.2406 -0.0542 0.9857 0.087 Uiso calc R 1 . .
    H H18B 0.1902 -0.0158 0.9156 0.087 Uiso calc R 1 . .
    H H18C 0.1872 -0.1472 0.9640 0.087 Uiso calc R 1 . .
    C C19 0.21951(10) -0.0063(4) 1.08845(11) 0.0638(7) Uani d . 1 . .
    H H19A 0.1937 -0.1081 1.0646 0.096 Uiso calc R 1 . .
    H H19B 0.2189 0.0382 1.1236 0.096 Uiso calc R 1 . .
    H H19C 0.2534 -0.0593 1.1053 0.096 Uiso calc R 1 . .
    C C20 0.21162(8) 0.4321(3) 1.11138(9) 0.0407(5) Uani d . 1 . .
    C C21 0.26530(9) 0.4262(4) 1.15526(10) 0.0491(6) Uani d . 1 . .
    H H21 0.2851 0.3512 1.1466 0.059 Uiso calc R 1 . .
    C C22 0.28909(10) 0.5325(4) 1.21193(11) 0.0603(7) Uani d . 1 . .
    H H22 0.3252 0.5284 1.2418 0.072 Uiso calc R 1 . .
    C C23 0.26000(11) 0.6446(4) 1.22477(11) 0.0618(7) Uani d . 1 . .
    H H23 0.2764 0.7173 1.2630 0.074 Uiso calc R 1 . .
    C C24 0.20683(11) 0.6495(4) 1.18132(12) 0.0603(7) Uani d . 1 . .
    H H24 0.1873 0.7256 1.1902 0.072 Uiso calc R 1 . .
    C C25 0.18209(9) 0.5423(3) 1.12451(11) 0.0493(6) Uani d . 1 . .
    H H25 0.1459 0.5441 1.0953 0.059 Uiso calc R 1 . .
_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
    Cl1 C3 . 1.742(2) ?
    O1 C7 . 1.355(3) ?
    O1 C8 . 1.408(2) ?
    O2 C7 . 1.204(3) ?
    O3 C17 . 1.239(3) ?
    N1 C14 . 1.280(3) ?
    N1 C15 . 1.400(3) ?
    N2 C16 . 1.358(3) ?
    N2 N3 . 1.400(2) ?
    N2 C19 . 1.464(3) ?
    N3 C17 . 1.412(3) ?
    N3 C20 . 1.431(3) ?
    C1 C2 . 1.379(3) ?
    C1 C6 . 1.384(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.375(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.366(3) ?
    C4 C5 . 1.386(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.380(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.481(3) ?
    C8 C9 . 1.368(3) ?
    C8 C13 . 1.371(3) ?
    C9 C10 . 1.377(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.387(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.380(3) ?
    C11 C14 . 1.472(3) ?
    C12 C13 . 1.389(3) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.371(3) ?
    C15 C17 . 1.430(3) ?
    C16 C18 . 1.484(3) ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C20 C21 . 1.382(3) ?
    C20 C25 . 1.383(3) ?
    C21 C22 . 1.375(3) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.374(3) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.369(3) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.379(3) ?
    C24 H24 . 0.9300 ?
    C25 H25 . 0.9300 ?
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
    C7 O1 C8 . . 120.77(18) ?
    C14 N1 C15 . . 120.2(2) ?
    C16 N2 N3 . . 107.82(16) ?
    C16 N2 C19 . . 125.42(19) ?
    N3 N2 C19 . . 118.44(18) ?
    N2 N3 C17 . . 108.53(17) ?
    N2 N3 C20 . . 118.83(16) ?
    C17 N3 C20 . . 122.04(18) ?
    C2 C1 C6 . . 121.0(2) ?
    C2 C1 H1 . . 119.5 ?
    C6 C1 H1 . . 119.5 ?
    C3 C2 C1 . . 118.5(2) ?
    C3 C2 H2 . . 120.8 ?
    C1 C2 H2 . . 120.8 ?
    C4 C3 C2 . . 122.0(2) ?
    C4 C3 Cl1 . . 119.2(2) ?
    C2 C3 Cl1 . . 118.9(2) ?
    C3 C4 C5 . . 118.9(2) ?
    C3 C4 H4 . . 120.5 ?
    C5 C4 H4 . . 120.5 ?
    C6 C5 C4 . . 120.5(2) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    C5 C6 C1 . . 119.1(2) ?
    C5 C6 C7 . . 122.5(2) ?
    C1 C6 C7 . . 118.4(2) ?
    O2 C7 O1 . . 123.7(2) ?
    O2 C7 C6 . . 124.4(2) ?
    O1 C7 C6 . . 111.9(2) ?
    C9 C8 C13 . . 121.4(2) ?
    C9 C8 O1 . . 115.8(2) ?
    C13 C8 O1 . . 122.7(2) ?
    C8 C9 C10 . . 119.7(2) ?
    C8 C9 H9 . . 120.1 ?
    C10 C9 H9 . . 120.1 ?
    C9 C10 C11 . . 120.9(2) ?
    C9 C10 H10 . . 119.6 ?
    C11 C10 H10 . . 119.6 ?
    C12 C11 C10 . . 117.8(2) ?
    C12 C11 C14 . . 120.1(2) ?
    C10 C11 C14 . . 122.1(2) ?
    C11 C12 C13 . . 122.0(2) ?
    C11 C12 H12 . . 119.0 ?
    C13 C12 H12 . . 119.0 ?
    C8 C13 C12 . . 118.1(2) ?
    C8 C13 H13 . . 120.9 ?
    C12 C13 H13 . . 120.9 ?
    N1 C14 C11 . . 121.7(2) ?
    N1 C14 H14 . . 119.1 ?
    C11 C14 H14 . . 119.1 ?
    C16 C15 N1 . . 122.2(2) ?
    C16 C15 C17 . . 108.37(19) ?
    N1 C15 C17 . . 129.3(2) ?
    N2 C16 C15 . . 109.73(19) ?
    N2 C16 C18 . . 121.21(19) ?
    C15 C16 C18 . . 129.0(2) ?
    O3 C17 N3 . . 122.4(2) ?
    O3 C17 C15 . . 132.6(2) ?
    N3 C17 C15 . . 105.01(19) ?
    C16 C18 H18A . . 109.5 ?
    C16 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C16 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    N2 C19 H19A . . 109.5 ?
    N2 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    N2 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C21 C20 C25 . . 120.4(2) ?
    C21 C20 N3 . . 121.0(2) ?
    C25 C20 N3 . . 118.50(19) ?
    C22 C21 C20 . . 119.3(2) ?
    C22 C21 H21 . . 120.4 ?
    C20 C21 H21 . . 120.4 ?
    C23 C22 C21 . . 120.6(2) ?
    C23 C22 H22 . . 119.7 ?
    C21 C22 H22 . . 119.7 ?
    C24 C23 C22 . . 120.0(2) ?
    C24 C23 H23 . . 120.0 ?
    C22 C23 H23 . . 120.0 ?
    C23 C24 C25 . . 120.4(2) ?
    C23 C24 H24 . . 119.8 ?
    C25 C24 H24 . . 119.8 ?
    C24 C25 C20 . . 119.3(2) ?
    C24 C25 H25 . . 120.4 ?
    C20 C25 H25 . . 120.4 ?
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
    C16 N2 N3 C17 . . . . -7.5(2) ?
    C19 N2 N3 C17 . . . . -157.56(18) ?
    C16 N2 N3 C20 . . . . -152.92(18) ?
    C19 N2 N3 C20 . . . . 57.0(3) ?
    C6 C1 C2 C3 . . . . -0.5(4) ?
    C1 C2 C3 C4 . . . . 0.1(4) ?
    C1 C2 C3 Cl1 . . . . -179.20(19) ?
    C2 C3 C4 C5 . . . . 0.6(4) ?
    Cl1 C3 C4 C5 . . . . 179.97(17) ?
    C3 C4 C5 C6 . . . . -1.1(3) ?
    C4 C5 C6 C1 . . . . 0.8(3) ?
    C4 C5 C6 C7 . . . . -176.8(2) ?
    C2 C1 C6 C5 . . . . 0.0(4) ?
    C2 C1 C6 C7 . . . . 177.7(2) ?
    C8 O1 C7 O2 . . . . -4.2(4) ?
    C8 O1 C7 C6 . . . . 173.80(18) ?
    C5 C6 C7 O2 . . . . 171.5(3) ?
    C1 C6 C7 O2 . . . . -6.1(4) ?
    C5 C6 C7 O1 . . . . -6.5(3) ?
    C1 C6 C7 O1 . . . . 175.9(2) ?
    C7 O1 C8 C9 . . . . -133.6(2) ?
    C7 O1 C8 C13 . . . . 49.8(3) ?
    C13 C8 C9 C10 . . . . -1.3(4) ?
    O1 C8 C9 C10 . . . . -178.0(2) ?
    C8 C9 C10 C11 . . . . 0.0(4) ?
    C9 C10 C11 C12 . . . . 1.8(4) ?
    C9 C10 C11 C14 . . . . -177.5(2) ?
    C10 C11 C12 C13 . . . . -2.3(4) ?
    C14 C11 C12 C13 . . . . 177.0(2) ?
    C9 C8 C13 C12 . . . . 0.9(4) ?
    O1 C8 C13 C12 . . . . 177.3(2) ?
    C11 C12 C13 C8 . . . . 1.0(4) ?
    C15 N1 C14 C11 . . . . 178.23(19) ?
    C12 C11 C14 N1 . . . . -170.3(2) ?
    C10 C11 C14 N1 . . . . 9.0(3) ?
    C14 N1 C15 C16 . . . . 178.8(2) ?
    C14 N1 C15 C17 . . . . -6.2(3) ?
    N3 N2 C16 C15 . . . . 6.8(2) ?
    C19 N2 C16 C15 . . . . 154.1(2) ?
    N3 N2 C16 C18 . . . . -171.50(19) ?
    C19 N2 C16 C18 . . . . -24.1(3) ?
    N1 C15 C16 N2 . . . . 172.45(18) ?
    C17 C15 C16 N2 . . . . -3.4(2) ?
    N1 C15 C16 C18 . . . . -9.5(4) ?
    C17 C15 C16 C18 . . . . 174.7(2) ?
    N2 N3 C17 O3 . . . . -172.80(18) ?
    C20 N3 C17 O3 . . . . -28.7(3) ?
    N2 N3 C17 C15 . . . . 5.3(2) ?
    C20 N3 C17 C15 . . . . 149.38(19) ?
    C16 C15 C17 O3 . . . . 176.6(2) ?
    N1 C15 C17 O3 . . . . 1.1(4) ?
    C16 C15 C17 N3 . . . . -1.3(2) ?
    N1 C15 C17 N3 . . . . -176.73(19) ?
    N2 N3 C20 C21 . . . . 29.5(3) ?
    C17 N3 C20 C21 . . . . -111.0(2) ?
    N2 N3 C20 C25 . . . . -153.43(19) ?
    C17 N3 C20 C25 . . . . 66.0(3) ?
    C25 C20 C21 C22 . . . . -0.5(3) ?
    N3 C20 C21 C22 . . . . 176.4(2) ?
    C20 C21 C22 C23 . . . . -0.5(4) ?
    C21 C22 C23 C24 . . . . 0.7(4) ?
    C22 C23 C24 C25 . . . . 0.0(4) ?
    C23 C24 C25 C20 . . . . -1.0(4) ?
    C21 C20 C25 C24 . . . . 1.3(3) ?
    N3 C20 C25 C24 . . . . -175.8(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
    _geom_hbond_publ_flag
    C18 H18C O3 1_545 0.96 2.46 3.405(3) 169 yes
    C19 H19A O3 1_545 0.96 2.58 3.497(3) 161 yes
    C2 H2 O3 6_575 0.93 2.53 3.219(3) 131 yes
