##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# 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     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2008-09-13
_journal_date_accepted     2008-09-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     10
_journal_page_first     o1965
_journal_page_last     o1966
_journal_paper_category     QO
_journal_coeditor_code     CI2671
_publ_contact_author_name     'Zhao-Fu Zhu'
_publ_contact_author_address
;
Department of Chemistry
Hebei Normal College of Science and Technology
Qinhuangdao 066600
People's Republic of China
;
_publ_contact_author_email     zhaofu_zhu@163.com
_publ_section_title
;\
A second monoclinic polymorph of
4-(2-hydroxy-4-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H-\
pyrazol-3(2H)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhao-Fu Zhu'
;
Department of Chemistry
Hebei Normal College of Science and Technology
Qinhuangdao 066600
People's Republic of China
;
    'Xi-Hai Shen'
;
Department of Chemistry
Hebei Normal College of Science and Technology
Qinhuangdao 066600
People's Republic of China
;
    'Xiao-Guang Tang'
;
Department of Chemistry
Hebei Normal College of Science and Technology
Qinhuangdao 066600
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-(2-hydroxy-4-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H-
pyrazol-3(2H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H19 N3 O3'
_chemical_formula_sum     'C19 H19 N3 O3'
_chemical_formula_iupac     'C19 H19 N3 O3'
_chemical_formula_weight     337.37
_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     30.581(3)
_cell_length_b     6.906(2)
_cell_length_c     17.059(3)
_cell_angle_alpha     90.00
_cell_angle_beta     110.500(2)
_cell_angle_gamma     90.00
_cell_volume     3374.6(12)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2554
_cell_measurement_theta_min     2.4
_cell_measurement_theta_max     25.6
_cell_measurement_temperature     298(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.27
_exptl_crystal_density_diffrn     1.328
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1424
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.9730
_exptl_absorpt_correction_T_max     0.9757
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(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     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9315
_diffrn_reflns_av_R_equivalents     0.0368
_diffrn_reflns_av_sigmaI/netI     0.0435
_diffrn_reflns_theta_min     1.42
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -36
_diffrn_reflns_limit_h_max     38
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     21
_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 >
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     3634
_reflns_number_gt     2355
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0802
_refine_ls_R_factor_gt     0.0483
_refine_ls_wR_factor_gt     0.1228
_refine_ls_wR_factor_ref     0.1446
_refine_ls_goodness_of_fit_ref     1.015
_refine_ls_restrained_S_all     1.015
_refine_ls_number_reflns     3634
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0710P)²+0.6977P] 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     <0.001
_refine_diff_density_max     0.188
_refine_diff_density_min     -0.201
_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, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT  (Bruker, 2007)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 0.13337(6) 0.6567(2) 0.02029(14) 0.0720(7) Uani d P 0.787(4) A 1
    H H1 0.1613 0.6337 0.0427 0.108 Uiso calc PR 0.787(4) A 1
    O O1' 0.1955(2) 1.2396(10) -0.0333(4) 0.071(3) Uani d P 0.213(4) A 2
    H H1' 0.1891 1.3241 -0.0693 0.106 Uiso calc PR 0.213(4) A 2
    O O2 0.03260(5) 1.1507(2) -0.13459(11) 0.0834(5) Uani d . 1 A .
    O O3 0.31552(5) 0.96750(18) 0.13504(9) 0.0628(4) Uani d . 1 . .
    N N1 0.22230(5) 0.7333(2) 0.08331(9) 0.0483(4) Uani d . 1 A .
    N N2 0.32298(5) 0.5274(2) 0.23447(9) 0.0494(4) Uani d . 1 . .
    N N3 0.34320(5) 0.6934(2) 0.21511(9) 0.0491(4) Uani d . 1 . .
    C C1 0.16608(6) 0.9540(2) -0.00342(11) 0.0450(4) Uani d . 1 A .
    C C2 0.12777(7) 0.8350(3) -0.01178(12) 0.0505(5) Uani d . 1 . .
    H H2 0.1327 0.7125 0.0124 0.061 Uiso calc PR 0.213(4) A 2
    C C3 0.08307(7) 0.8956(3) -0.05505(13) 0.0586(5) Uani d . 1 A .
    H H3 0.0580 0.8144 -0.0601 0.070 Uiso calc R 1 . .
    C C4 0.07548(7) 1.0762(3) -0.09092(13) 0.0573(5) Uani d . 1 . .
    C C5 0.11288(7) 1.1968(3) -0.08392(12) 0.0586(5) Uani d . 1 A .
    H H5 0.1078 1.3190 -0.1084 0.070 Uiso calc R 1 . .
    C C6 0.15705(6) 1.1355(3) -0.04112(12) 0.0511(5) Uani d . 1 . .
    H H6 0.1820 1.2171 -0.0369 0.061 Uiso calc PR 0.787(4) A 1
    C C7 0.21326(6) 0.8961(2) 0.04376(11) 0.0468(4) Uani d . 1 . .
    H H7 0.2378 0.9780 0.0458 0.056 Uiso calc R 1 A .
    C C8 0.26761(6) 0.6861(2) 0.13421(10) 0.0437(4) Uani d . 1 . .
    C C9 0.27825(6) 0.5207(2) 0.18071(11) 0.0458(4) Uani d . 1 A .
    C C10 0.24772(7) 0.3533(3) 0.17836(14) 0.0658(6) Uani d . 1 . .
    H H10A 0.2179 0.3725 0.1351 0.099 Uiso calc R 1 A .
    H H10B 0.2436 0.3411 0.2314 0.099 Uiso calc R 1 . .
    H H10C 0.2618 0.2375 0.1670 0.099 Uiso calc R 1 . .
    C C11 0.35235(7) 0.3601(3) 0.26802(13) 0.0625(6) Uani d . 1 . .
    H H11A 0.3354 0.2677 0.2883 0.094 Uiso calc R 1 . .
    H H11B 0.3798 0.4001 0.3132 0.094 Uiso calc R 1 . .
    H H11C 0.3613 0.3019 0.2248 0.094 Uiso calc R 1 . .
    C C12 0.30866(6) 0.8026(2) 0.15627(11) 0.0468(4) Uani d . 1 A .
    C C13 0.38321(6) 0.7784(2) 0.27470(11) 0.0460(4) Uani d . 1 . .
    C C14 0.39069(7) 0.7743(3) 0.35949(12) 0.0559(5) Uani d . 1 . .
    H H14 0.3703 0.7077 0.3795 0.067 Uiso calc R 1 . .
    C C15 0.42859(8) 0.8700(3) 0.41369(14) 0.0673(6) Uani d . 1 . .
    H H15 0.4341 0.8665 0.4709 0.081 Uiso calc R 1 . .
    C C16 0.45828(8) 0.9701(3) 0.38483(15) 0.0717(6) Uani d . 1 . .
    H H16 0.4836 1.0358 0.4221 0.086 Uiso calc R 1 . .
    C C17 0.45062(7) 0.9736(3) 0.30043(15) 0.0672(6) Uani d . 1 . .
    H H17 0.4708 1.0424 0.2807 0.081 Uiso calc R 1 . .
    C C18 0.41342(7) 0.8764(3) 0.24504(13) 0.0545(5) Uani d . 1 . .
    H H18 0.4087 0.8768 0.1881 0.065 Uiso calc R 1 . .
    C C19 -0.00684(9) 1.0308(4) -0.1448(3) 0.1287(14) Uani d . 1 . .
    H H19A -0.0037 0.9120 -0.1715 0.193 Uiso calc R 1 A .
    H H19B -0.0347 1.0966 -0.1788 0.193 Uiso calc R 1 . .
    H H19C -0.0088 1.0030 -0.0910 0.193 Uiso calc R 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
    O1 C2 . 1.333(2) ?
    O1 H1 . 0.82 ?
    O1' C6 . 1.345(6) ?
    O1' H1' . 0.82 ?
    O2 C4 . 1.362(2) ?
    O2 C19 . 1.422(3) ?
    O3 C12 . 1.235(2) ?
    N1 C7 . 1.291(2) ?
    N1 C8 . 1.392(2) ?
    N2 C9 . 1.355(2) ?
    N2 N3 . 1.3959(19) ?
    N2 C11 . 1.452(2) ?
    N3 C12 . 1.396(2) ?
    N3 C13 . 1.416(2) ?
    C1 C6 . 1.392(2) ?
    C1 C2 . 1.397(2) ?
    C1 C7 . 1.441(2) ?
    C2 C3 . 1.372(3) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.373(3) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.386(3) ?
    C5 C6 . 1.359(3) ?
    C5 H5 . 0.93 ?
    C6 H6 . 0.93 ?
    C7 H7 . 0.93 ?
    C8 C9 . 1.363(2) ?
    C8 C12 . 1.426(2) ?
    C9 C10 . 1.478(2) ?
    C10 H10A . 0.96 ?
    C10 H10B . 0.96 ?
    C10 H10C . 0.96 ?
    C11 H11A . 0.96 ?
    C11 H11B . 0.96 ?
    C11 H11C . 0.96 ?
    C13 C18 . 1.376(3) ?
    C13 C14 . 1.383(3) ?
    C14 C15 . 1.373(3) ?
    C14 H14 . 0.93 ?
    C15 C16 . 1.363(3) ?
    C15 H15 . 0.93 ?
    C16 C17 . 1.376(3) ?
    C16 H16 . 0.93 ?
    C17 C18 . 1.373(3) ?
    C17 H17 . 0.93 ?
    C18 H18 . 0.93 ?
    C19 H19A . 0.96 ?
    C19 H19B . 0.96 ?
    C19 H19C . 0.96 ?
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
    C2 O1 H1 . . 109.5 ?
    C6 O1' H1' . . 109.5 ?
    C4 O2 C19 . . 117.40(17) ?
    C7 N1 C8 . . 120.96(15) ?
    C9 N2 N3 . . 107.07(13) ?
    C9 N2 C11 . . 125.34(14) ?
    N3 N2 C11 . . 118.86(14) ?
    N2 N3 C12 . . 109.12(13) ?
    N2 N3 C13 . . 120.92(14) ?
    C12 N3 C13 . . 122.55(14) ?
    C6 C1 C2 . . 117.34(16) ?
    C6 C1 C7 . . 120.37(16) ?
    C2 C1 C7 . . 122.27(16) ?
    O1 C2 C3 . . 117.58(18) ?
    O1 C2 C1 . . 121.24(18) ?
    C3 C2 C1 . . 121.16(17) ?
    C3 C2 H2 . . 119.4 ?
    C1 C2 H2 . . 119.4 ?
    C2 C3 C4 . . 119.87(18) ?
    C2 C3 H3 . . 120.1 ?
    C4 C3 H3 . . 120.1 ?
    O2 C4 C3 . . 124.53(18) ?
    O2 C4 C5 . . 115.33(17) ?
    C3 C4 C5 . . 120.14(18) ?
    C6 C5 C4 . . 119.62(17) ?
    C6 C5 H5 . . 120.2 ?
    C4 C5 H5 . . 120.2 ?
    O1' C6 C5 . . 123.9(3) ?
    O1' C6 C1 . . 114.2(3) ?
    C5 C6 C1 . . 121.86(17) ?
    C5 C6 H6 . . 119.1 ?
    C1 C6 H6 . . 119.1 ?
    N1 C7 C1 . . 121.53(17) ?
    N1 C7 H7 . . 119.2 ?
    C1 C7 H7 . . 119.2 ?
    C9 C8 N1 . . 122.81(16) ?
    C9 C8 C12 . . 108.09(15) ?
    N1 C8 C12 . . 128.62(15) ?
    N2 C9 C8 . . 110.13(15) ?
    N2 C9 C10 . . 121.55(16) ?
    C8 C9 C10 . . 128.31(17) ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N2 C11 H11A . . 109.5 ?
    N2 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N2 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    O3 C12 N3 . . 123.06(16) ?
    O3 C12 C8 . . 131.86(17) ?
    N3 C12 C8 . . 105.01(14) ?
    C18 C13 C14 . . 120.51(17) ?
    C18 C13 N3 . . 117.56(17) ?
    C14 C13 N3 . . 121.82(17) ?
    C15 C14 C13 . . 119.09(19) ?
    C15 C14 H14 . . 120.5 ?
    C13 C14 H14 . . 120.5 ?
    C16 C15 C14 . . 120.8(2) ?
    C16 C15 H15 . . 119.6 ?
    C14 C15 H15 . . 119.6 ?
    C15 C16 C17 . . 119.7(2) ?
    C15 C16 H16 . . 120.1 ?
    C17 C16 H16 . . 120.1 ?
    C18 C17 C16 . . 120.5(2) ?
    C18 C17 H17 . . 119.7 ?
    C16 C17 H17 . . 119.7 ?
    C17 C18 C13 . . 119.2(2) ?
    C17 C18 H18 . . 120.4 ?
    C13 C18 H18 . . 120.4 ?
    O2 C19 H19A . . 109.5 ?
    O2 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    O2 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 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
    C9 N2 N3 C12 . . . . 7.87(18) ?
    C11 N2 N3 C12 . . . . 157.19(16) ?
    C9 N2 N3 C13 . . . . 158.51(16) ?
    C11 N2 N3 C13 . . . . -52.2(2) ?
    C6 C1 C2 O1 . . . . 178.03(19) ?
    C7 C1 C2 O1 . . . . -3.5(3) ?
    C6 C1 C2 C3 . . . . -0.4(3) ?
    C7 C1 C2 C3 . . . . 178.12(18) ?
    O1 C2 C3 C4 . . . . -178.5(2) ?
    C1 C2 C3 C4 . . . . -0.1(3) ?
    C19 O2 C4 C3 . . . . -1.2(4) ?
    C19 O2 C4 C5 . . . . 178.8(2) ?
    C2 C3 C4 O2 . . . . -179.54(19) ?
    C2 C3 C4 C5 . . . . 0.4(3) ?
    O2 C4 C5 C6 . . . . 179.70(19) ?
    C3 C4 C5 C6 . . . . -0.2(3) ?
    C4 C5 C6 O1' . . . . 177.8(5) ?
    C4 C5 C6 C1 . . . . -0.2(3) ?
    C2 C1 C6 O1' . . . . -177.6(4) ?
    C7 C1 C6 O1' . . . . 3.8(5) ?
    C2 C1 C6 C5 . . . . 0.6(3) ?
    C7 C1 C6 C5 . . . . -177.99(18) ?
    C8 N1 C7 C1 . . . . -174.67(15) ?
    C6 C1 C7 N1 . . . . 175.94(17) ?
    C2 C1 C7 N1 . . . . -2.5(3) ?
    C7 N1 C8 C9 . . . . 176.18(17) ?
    C7 N1 C8 C12 . . . . 5.1(3) ?
    N3 N2 C9 C8 . . . . -6.7(2) ?
    C11 N2 C9 C8 . . . . -153.47(18) ?
    N3 N2 C9 C10 . . . . 174.23(17) ?
    C11 N2 C9 C10 . . . . 27.5(3) ?
    N1 C8 C9 N2 . . . . -169.67(15) ?
    C12 C8 C9 N2 . . . . 3.0(2) ?
    N1 C8 C9 C10 . . . . 9.3(3) ?
    C12 C8 C9 C10 . . . . -177.97(18) ?
    N2 N3 C12 O3 . . . . 171.32(17) ?
    C13 N3 C12 O3 . . . . 21.3(3) ?
    N2 N3 C12 C8 . . . . -5.92(18) ?
    C13 N3 C12 C8 . . . . -155.98(16) ?
    C9 C8 C12 O3 . . . . -175.1(2) ?
    N1 C8 C12 O3 . . . . -2.9(3) ?
    C9 C8 C12 N3 . . . . 1.84(19) ?
    N1 C8 C12 N3 . . . . 174.00(16) ?
    N2 N3 C13 C18 . . . . 150.64(16) ?
    C12 N3 C13 C18 . . . . -62.7(2) ?
    N2 N3 C13 C14 . . . . -33.2(2) ?
    C12 N3 C13 C14 . . . . 113.5(2) ?
    C18 C13 C14 C15 . . . . 0.2(3) ?
    N3 C13 C14 C15 . . . . -175.85(18) ?
    C13 C14 C15 C16 . . . . 0.8(3) ?
    C14 C15 C16 C17 . . . . -0.8(3) ?
    C15 C16 C17 C18 . . . . -0.3(3) ?
    C16 C17 C18 C13 . . . . 1.3(3) ?
    C14 C13 C18 C17 . . . . -1.3(3) ?
    N3 C13 C18 C17 . . . . 174.94(18) ?
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
    O1 H1 N1 . 0.82 1.88 2.605(2) 147
    O1' H1' O3 7_575 0.82 1.80 2.609(6) 169
    C7 H7 O3 . 0.93 2.33 3.006(5) 129
