##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL97'
_journal_date_recd_electronic     2006-03-23
_journal_date_accepted     2006-03-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      5
_journal_page_first     o1756
_journal_page_last     o1758
_journal_paper_category     EO
_journal_coeditor_code     AT2023
_publ_contact_author_name     'Hua-Zheng Yang'
_publ_contact_author_address
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin Road No. 94
Tianjin
People's Republic of China
;
_publ_contact_author_email     'youquan_zhu@mail.nankai.edu.cn'
_publ_contact_author_fax     '022-23503438'
_publ_contact_author_phone     '022-23503799'
_publ_section_title
;\
Ethyl
5-amino-1-(5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl)-3-methyl-\
1H-pyrazole-4-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Jun-Fei Li'
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin Road No. 94
Tianjin
People's Republic of China
;
    'Hai-Bin Song'
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin Road No. 94
Tianjin
People's Republic of China
;
    'You-Quan Zhu'
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin Road No. 94
Tianjin
People's Republic of China
;
    'Hua-Zheng Yang'
;
State Key Laboratory and Institute of Elemento-Organic Chemistry
Nankai University
Tianjin
Weijin Road No. 94
Tianjin
People's Republic of China
;
data_I
_chemical_name_systematic
;
Ethyl 5-amino-1-(5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonyl)
-3-methyl-1H-pyrazole-4-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H20 N6 O3'
_chemical_formula_sum     'C18 H20 N6 O3'
_chemical_formula_iupac     'C18 H20 N6 O3'
_chemical_formula_weight     368.40
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P bca'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     10.5990(14)
_cell_length_b     10.9782(14)
_cell_length_c     31.017(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3609.0(8)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4591
_cell_measurement_theta_min     2.75
_cell_measurement_theta_max     24.33
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.28
_exptl_crystal_density_diffrn     1.356
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1552
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS;  Bruker, 1999)'
_exptl_absorpt_correction_T_min     0.956
_exptl_absorpt_correction_T_max     0.973
_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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19243
_diffrn_reflns_av_R_equivalents     0.0413
_diffrn_reflns_av_sigmaI/netI     0.0320
_diffrn_reflns_theta_min     2.33
_diffrn_reflns_theta_max     26.41
_diffrn_reflns_theta_full     26.41
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     38
_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 > 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     3691
_reflns_number_gt     2348
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0812
_refine_ls_R_factor_gt     0.0421
_refine_ls_wR_factor_gt     0.0957
_refine_ls_wR_factor_ref     0.1156
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     3691
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w = 1/[σ²(Fo²)+(0.0497P)²+0.794P] 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     0.159
_refine_diff_density_min     -0.179
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1999)'
_computing_publication_material     'SHELXTL'
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
    O O1 0.22909(14) -0.08346(13) 0.03895(4) 0.0602(4) Uani d . 1 . .
    O O2 0.20541(14) 0.13799(13) -0.11619(4) 0.0600(4) Uani d . 1 . .
    O O3 0.08046(13) 0.30093(12) -0.10665(4) 0.0560(4) Uani d . 1 . .
    N N1 -0.04454(17) 0.18407(16) 0.10263(6) 0.0532(5) Uani d . 1 . .
    H H1A -0.0384(19) 0.2062(18) 0.0745(7) 0.067(7) Uiso d . 1 . .
    H H1B -0.094(2) 0.2192(19) 0.1195(7) 0.057(6) Uiso d . 1 . .
    N N2 0.02915(15) 0.05381(14) 0.15674(5) 0.0449(4) Uani d . 1 . .
    N N3 0.10686(16) -0.04613(15) 0.16353(5) 0.0521(4) Uani d . 1 . .
    N N4 0.24408(17) -0.01182(17) -0.04180(6) 0.0497(4) Uani d . 1 . .
    H H4D 0.264(2) -0.074(2) -0.0230(8) 0.084(8) Uiso d . 1 . .
    H H4E 0.257(2) -0.0089(19) -0.0690(7) 0.064(7) Uiso d . 1 . .
    N N5 0.12499(13) 0.08054(13) 0.01547(4) 0.0384(4) Uani d . 1 . .
    N N6 0.04520(14) 0.18013(13) 0.02091(5) 0.0421(4) Uani d . 1 . .
    C C1 0.02928(16) 0.09152(15) 0.11527(6) 0.0379(4) Uani d . 1 . .
    C C2 0.11439(16) 0.01459(15) 0.09312(5) 0.0376(4) Uani d . 1 . .
    C C3 0.15728(17) -0.06842(17) 0.12572(6) 0.0457(5) Uani d . 1 . .
    C C4 0.2480(2) -0.1724(2) 0.12210(7) 0.0692(7) Uani d . 1 . .
    H H4A 0.2606 -0.2082 0.1500 0.104 Uiso calc R 1 . .
    H H4B 0.3272 -0.1432 0.1112 0.104 Uiso calc R 1 . .
    H H4C 0.2144 -0.2326 0.1028 0.104 Uiso calc R 1 . .
    C C5 0.15865(17) 0.00016(16) 0.04925(6) 0.0408(4) Uani d . 1 . .
    C C6 0.16706(16) 0.07477(16) -0.02668(5) 0.0377(4) Uani d . 1 . .
    C C7 0.11516(15) 0.17387(16) -0.04793(5) 0.0383(4) Uani d . 1 . .
    C C8 0.03895(16) 0.23401(16) -0.01666(6) 0.0403(4) Uani d . 1 . .
    C C9 -0.0450(2) 0.34180(18) -0.02189(7) 0.0560(5) Uani d . 1 . .
    H H9A -0.1181 0.3191 -0.0383 0.084 Uiso calc R 1 . .
    H H9B -0.0002 0.4052 -0.0368 0.084 Uiso calc R 1 . .
    H H9C -0.0706 0.3706 0.0060 0.084 Uiso calc R 1 . .
    C C10 -0.04592(17) 0.09805(17) 0.19158(6) 0.0442(5) Uani d . 1 . .
    C C11 -0.0350(2) 0.21728(19) 0.20475(6) 0.0570(5) Uani d . 1 . .
    H H11 0.0201 0.2699 0.1906 0.068 Uiso calc R 1 . .
    C C12 -0.1061(2) 0.2581(2) 0.23896(7) 0.0731(7) Uani d . 1 . .
    H H12 -0.0990 0.3385 0.2481 0.088 Uiso calc R 1 . .
    C C13 -0.1869(2) 0.1808(3) 0.25954(7) 0.0768(7) Uani d . 1 . .
    H H13 -0.2353 0.2090 0.2825 0.092 Uiso calc R 1 . .
    C C14 -0.1974(2) 0.0621(3) 0.24665(7) 0.0754(7) Uani d . 1 . .
    H H14 -0.2521 0.0097 0.2610 0.090 Uiso calc R 1 . .
    C C15 -0.1269(2) 0.0198(2) 0.21236(6) 0.0595(6) Uani d . 1 . .
    H H15 -0.1340 -0.0608 0.2034 0.071 Uiso calc R 1 . .
    C C16 0.13856(18) 0.19975(17) -0.09300(6) 0.0439(4) Uani d . 1 . .
    C C17 0.0907(2) 0.3301(2) -0.15207(6) 0.0676(6) Uani d . 1 . .
    H H17A 0.0474 0.2692 -0.1692 0.081 Uiso calc R 1 . .
    H H17B 0.1786 0.3319 -0.1607 0.081 Uiso calc R 1 . .
    C C18 0.0321(3) 0.4517(2) -0.15865(8) 0.0857(8) Uani d . 1 . .
    H H18A -0.0542 0.4494 -0.1493 0.129 Uiso calc R 1 . .
    H H18B 0.0352 0.4726 -0.1887 0.129 Uiso calc R 1 . .
    H H18C 0.0773 0.5116 -0.1422 0.129 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
    O1 C5 . 1.226(2) yes
    O2 C16 . 1.216(2) yes
    O3 C16 . 1.339(2) no
    O3 C17 . 1.449(2) no
    N1 C1 . 1.341(2) yes
    N1 H1A . 0.91(2) no
    N1 H1B . 0.84(2) no
    N2 C1 . 1.351(2) yes
    N2 N3 . 1.388(2) yes
    N2 C10 . 1.427(2) yes
    N3 C3 . 1.312(2) yes
    N4 C6 . 1.338(2) no
    N4 H4D . 0.92(2) no
    N4 H4E . 0.85(2) no
    N5 C6 . 1.383(2) yes
    N5 N6 . 1.3925(19) yes
    N5 C5 . 1.416(2) yes
    N6 C8 . 1.309(2) yes
    C1 C2 . 1.414(2) no
    C2 C3 . 1.435(2) no
    C2 C5 . 1.448(2) no
    C3 C4 . 1.497(3) no
    C4 H4A . 0.9600 no
    C4 H4B . 0.9600 no
    C4 H4C . 0.9600 no
    C6 C7 . 1.386(2) no
    C7 C8 . 1.424(2) no
    C7 C16 . 1.448(2) no
    C8 C9 . 1.489(3) no
    C9 H9A . 0.9600 no
    C9 H9B . 0.9600 no
    C9 H9C . 0.9600 no
    C10 C15 . 1.375(3) no
    C10 C11 . 1.376(3) no
    C11 C12 . 1.377(3) no
    C11 H11 . 0.9300 no
    C12 C13 . 1.365(3) no
    C12 H12 . 0.9300 no
    C13 C14 . 1.368(4) no
    C13 H13 . 0.9300 no
    C14 C15 . 1.380(3) no
    C14 H14 . 0.9300 no
    C15 H15 . 0.9300 no
    C17 C18 . 1.486(3) no
    C17 H17A . 0.9700 no
    C17 H17B . 0.9700 no
    C18 H18A . 0.9600 no
    C18 H18B . 0.9600 no
    C18 H18C . 0.9600 no
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
    C16 O3 C17 . . 117.16(15) no
    C1 N1 H1A . . 116.2(13) no
    C1 N1 H1B . . 122.3(14) no
    H1A N1 H1B . . 121(2) no
    C1 N2 N3 . . 112.71(14) no
    C1 N2 C10 . . 128.10(15) no
    N3 N2 C10 . . 119.01(14) no
    C3 N3 N2 . . 104.68(14) no
    C6 N4 H4D . . 116.4(15) no
    C6 N4 H4E . . 114.7(15) no
    H4D N4 H4E . . 128(2) no
    C6 N5 N6 . . 110.26(13) no
    C6 N5 C5 . . 126.16(15) no
    N6 N5 C5 . . 123.56(13) no
    C8 N6 N5 . . 106.12(13) no
    N1 C1 N2 . . 120.66(16) yes
    N1 C1 C2 . . 133.05(17) yes
    N2 C1 C2 . . 106.28(15) yes
    C1 C2 C3 . . 103.81(15) no
    C1 C2 C5 . . 136.79(16) no
    C3 C2 C5 . . 119.35(16) no
    N3 C3 C2 . . 112.49(16) no
    N3 C3 C4 . . 118.10(17) no
    C2 C3 C4 . . 129.41(17) no
    C3 C4 H4A . . 109.5 no
    C3 C4 H4B . . 109.5 no
    H4A C4 H4B . . 109.5 no
    C3 C4 H4C . . 109.5 no
    H4A C4 H4C . . 109.5 no
    H4B C4 H4C . . 109.5 no
    O1 C5 N5 . . 115.31(15) yes
    O1 C5 C2 . . 121.62(16) yes
    N5 C5 C2 . . 123.08(16) yes
    N4 C6 N5 . . 124.10(17) yes
    N4 C6 C7 . . 129.30(17) yes
    N5 C6 C7 . . 106.60(14) yes
    C6 C7 C8 . . 105.39(15) no
    C6 C7 C16 . . 123.03(16) no
    C8 C7 C16 . . 131.57(17) no
    N6 C8 C7 . . 111.60(16) no
    N6 C8 C9 . . 119.10(15) no
    C7 C8 C9 . . 129.27(16) no
    C8 C9 H9A . . 109.5 no
    C8 C9 H9B . . 109.5 no
    H9A C9 H9B . . 109.5 no
    C8 C9 H9C . . 109.5 no
    H9A C9 H9C . . 109.5 no
    H9B C9 H9C . . 109.5 no
    C15 C10 C11 . . 120.55(18) no
    C15 C10 N2 . . 119.35(17) no
    C11 C10 N2 . . 120.08(17) no
    C10 C11 C12 . . 119.5(2) no
    C10 C11 H11 . . 120.3 no
    C12 C11 H11 . . 120.3 no
    C13 C12 C11 . . 120.1(2) no
    C13 C12 H12 . . 119.9 no
    C11 C12 H12 . . 119.9 no
    C12 C13 C14 . . 120.4(2) no
    C12 C13 H13 . . 119.8 no
    C14 C13 H13 . . 119.8 no
    C13 C14 C15 . . 120.2(2) no
    C13 C14 H14 . . 119.9 no
    C15 C14 H14 . . 119.9 no
    C10 C15 C14 . . 119.3(2) no
    C10 C15 H15 . . 120.4 no
    C14 C15 H15 . . 120.4 no
    O2 C16 O3 . . 122.92(17) yes
    O2 C16 C7 . . 124.15(18) yes
    O3 C16 C7 . . 112.91(16) yes
    O3 C17 C18 . . 107.50(19) no
    O3 C17 H17A . . 110.2 no
    C18 C17 H17A . . 110.2 no
    O3 C17 H17B . . 110.2 no
    C18 C17 H17B . . 110.2 no
    H17A C17 H17B . . 108.5 no
    C17 C18 H18A . . 109.5 no
    C17 C18 H18B . . 109.5 no
    H18A C18 H18B . . 109.5 no
    C17 C18 H18C . . 109.5 no
    H18A C18 H18C . . 109.5 no
    H18B C18 H18C . . 109.5 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C1 N2 N3 C3 . . . . 1.2(2) no
    C10 N2 N3 C3 . . . . 176.73(16) no
    C6 N5 N6 C8 . . . . -0.25(18) no
    C5 N5 N6 C8 . . . . 178.36(15) no
    N3 N2 C1 N1 . . . . 177.31(16) no
    C10 N2 C1 N1 . . . . 2.3(3) no
    N3 N2 C1 C2 . . . . -1.6(2) no
    C10 N2 C1 C2 . . . . -176.58(17) no
    N1 C1 C2 C3 . . . . -177.5(2) yes
    N2 C1 C2 C3 . . . . 1.22(18) yes
    N1 C1 C2 C5 . . . . -0.3(4) yes
    N2 C1 C2 C5 . . . . 178.42(19) yes
    N2 N3 C3 C2 . . . . -0.4(2) no
    N2 N3 C3 C4 . . . . 179.69(18) no
    C1 C2 C3 N3 . . . . -0.5(2) yes
    C5 C2 C3 N3 . . . . -178.34(16) yes
    C1 C2 C3 C4 . . . . 179.4(2) yes
    C5 C2 C3 C4 . . . . 1.6(3) no
    C6 N5 C5 O1 . . . . -2.1(3) yes
    N6 N5 C5 O1 . . . . 179.49(15) yes
    C6 N5 C5 C2 . . . . 177.60(16) yes
    N6 N5 C5 C2 . . . . -0.8(2) yes
    C1 C2 C5 O1 . . . . -174.70(19) yes
    C3 C2 C5 O1 . . . . 2.2(3) yes
    C1 C2 C5 N5 . . . . 5.6(3) yes
    C3 C2 C5 N5 . . . . -177.54(16) yes
    N6 N5 C6 N4 . . . . -179.29(16) no
    C5 N5 C6 N4 . . . . 2.1(3) no
    N6 N5 C6 C7 . . . . 1.31(18) no
    C5 N5 C6 C7 . . . . -177.26(15) no
    N4 C6 C7 C8 . . . . 178.88(18) yes
    N5 C6 C7 C8 . . . . -1.75(18) yes
    N4 C6 C7 C16 . . . . 0.1(3) yes
    N5 C6 C7 C16 . . . . 179.45(15) yes
    N5 N6 C8 C7 . . . . -0.91(19) no
    N5 N6 C8 C9 . . . . 177.19(15) no
    C6 C7 C8 N6 . . . . 1.7(2) no
    C16 C7 C8 N6 . . . . -179.64(17) no
    C6 C7 C8 C9 . . . . -176.14(18) no
    C16 C7 C8 C9 . . . . 2.5(3) no
    C1 N2 C10 C15 . . . . 119.3(2) no
    N3 N2 C10 C15 . . . . -55.4(2) no
    C1 N2 C10 C11 . . . . -62.1(3) no
    N3 N2 C10 C11 . . . . 123.1(2) no
    C15 C10 C11 C12 . . . . -0.2(3) no
    N2 C10 C11 C12 . . . . -178.69(19) no
    C10 C11 C12 C13 . . . . -0.1(4) no
    C11 C12 C13 C14 . . . . 0.5(4) no
    C12 C13 C14 C15 . . . . -0.6(4) no
    C11 C10 C15 C14 . . . . 0.1(3) no
    N2 C10 C15 C14 . . . . 178.61(19) no
    C13 C14 C15 C10 . . . . 0.3(4) no
    C17 O3 C16 O2 . . . . 5.4(3) no
    C17 O3 C16 C7 . . . . -175.78(17) no
    C6 C7 C16 O2 . . . . -0.2(3) no
    C8 C7 C16 O2 . . . . -178.67(18) no
    C6 C7 C16 O3 . . . . -179.06(15) no
    C8 C7 C16 O3 . . . . 2.5(3) no
    C16 O3 C17 C18 . . . . -173.76(19) no
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
    N4 H4E O2 . 0.85(2) 2.25(2) 2.863(3) 129.1(18)
    N4 H4D O1 . 0.92(2) 1.96(2) 2.630(2) 128(2)
    N1 H1B O2 4_455 0.84(2) 2.64(2) 3.319(2) 139.2(17)
    N1 H1A N6 . 0.91(2) 1.91(2) 2.708(2) 146.2(19)
