##############################################################################
###                                                                        ###
###        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     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2006-09-18
_journal_date_accepted     2006-09-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     10
_journal_page_first     o4758
_journal_page_last     o4760
_journal_paper_category     EO
_journal_coeditor_code     CI2176
_publ_contact_author_name     'Prof. Sun, Yu-Xi'
_publ_contact_author_address
;
      Department of Chemistry
      Qufu Normal University
      Qufu 273165
      P.R.China
;
_publ_contact_author_email     yuxisun@163.com
_publ_contact_author_fax     '0086-537-4456305'
_publ_contact_author_phone     '0086-537-4451672'
_publ_section_title
;\
4-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]\
benzoic acid methanol solvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Sun, Yu-Xi'
;     Department of Chemistry
      Qufu Normal University
      Qufu 273165
      People's Republic of China
;
    'Xie, Xue-Hui'
;     College of Life Science
      Qufu Normal University
      Qufu 273165
      People's Republic of China
;
    'Zhang, Ran'
;     Department of Chemistry
      Qufu Normal University
      Qufu 273165
      People's Republic of China
;
    'Zhang, Li-Feng'
;     Department of Chemistry
      Qufu Normal University
      Qufu 273165
      People's Republic of China
;
    'Xu, Lai-Xiang'
;     College of Life Science
      Qufu Normal University
      Qufu 273165
      People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]benzoic
acid methanol solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H17 N3 O3, C H4 O'
_chemical_formula_sum     'C20 H21 N3 O4'
_chemical_formula_iupac     'C19 H17 N3 O3, C H4 O'
_chemical_formula_weight     367.40
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.4270(7)
_cell_length_b     10.2516(8)
_cell_length_c     10.3014(8)
_cell_angle_alpha     74.4500(10)
_cell_angle_beta     85.6730(10)
_cell_angle_gamma     75.6650(10)
_cell_volume     929.20(12)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2860
_cell_measurement_theta_min     2.54
_cell_measurement_theta_max     26.95
_cell_measurement_temperature     295(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.313
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     388
_exptl_absorpt_coefficient_mu     0.093
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9594
_exptl_absorpt_correction_T_max     0.9726
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(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 APEX area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6972
_diffrn_reflns_av_R_equivalents     0.0241
_diffrn_reflns_av_sigmaI/netI     0.0385
_diffrn_reflns_theta_min     2.05
_diffrn_reflns_theta_max     26.50
_diffrn_reflns_theta_full     26.50
_diffrn_measured_fraction_theta_max     0.977
_diffrn_measured_fraction_theta_full     0.977
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_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     3760
_reflns_number_gt     2595
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0797
_refine_ls_R_factor_gt     0.0591
_refine_ls_wR_factor_gt     0.1622
_refine_ls_wR_factor_ref     0.1764
_refine_ls_goodness_of_fit_ref     1.090
_refine_ls_restrained_S_all     1.092
_refine_ls_number_reflns     3760
_refine_ls_number_parameters     259
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0943P)²+0.0586P] 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     0.381
_refine_diff_density_min     -0.228
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.029(7)
_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     'SMART (Bruker, 2002)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2002)'
_computing_data_reduction     'SAINT-Plus'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2002)'
_computing_publication_material     'SHELXL97'
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 0.35079(16) 0.70738(15) 0.57502(16) 0.0749(5) Uani d . 1 . .
    O O2 0.58626(19) 1.38188(18) -0.13930(19) 0.0993(7) Uani d . 1 . .
    H H2 0.6204 1.4130 -0.2135 0.149 Uiso calc R 1 . .
    O O3 0.7622(2) 1.20133(18) -0.1431(2) 0.1165(8) Uani d . 1 . .
    N N1 0.16205(17) 0.77815(16) 0.71427(16) 0.0571(4) Uani d . 1 . .
    N N2 0.06437(17) 0.90351(16) 0.71706(15) 0.0557(4) Uani d . 1 . .
    N N3 0.29010(17) 1.02808(17) 0.44551(16) 0.0544(4) Uani d . 1 . .
    C C1 0.1194(2) 0.6504(2) 0.76516(19) 0.0550(5) Uani d . 1 . .
    C C2 0.2234(2) 0.5341(2) 0.8248(2) 0.0667(6) Uani d . 1 . .
    H H2A 0.3184 0.5401 0.8356 0.080 Uiso calc R 1 . .
    C C3 0.1848(3) 0.4084(2) 0.8685(2) 0.0801(7) Uani d . 1 . .
    H H3 0.2551 0.3284 0.9070 0.096 Uiso calc R 1 . .
    C C4 0.0452(3) 0.3997(3) 0.8559(2) 0.0838(8) Uani d . 1 . .
    H H4A 0.0199 0.3144 0.8860 0.101 Uiso calc R 1 . .
    C C5 -0.0575(3) 0.5170(3) 0.7988(3) 0.0880(8) Uani d . 1 . .
    H H5 -0.1535 0.5115 0.7919 0.106 Uiso calc R 1 . .
    C C6 -0.0213(2) 0.6424(3) 0.7517(2) 0.0713(6) Uani d . 1 . .
    H H6 -0.0914 0.7215 0.7109 0.086 Uiso calc R 1 . .
    C C7 0.2604(2) 0.8026(2) 0.6089(2) 0.0550(5) Uani d . 1 . .
    C C8 0.22671(19) 0.9496(2) 0.55489(18) 0.0507(5) Uani d . 1 . .
    C C9 0.1104(2) 1.0061(2) 0.62592(18) 0.0522(5) Uani d . 1 . .
    C C10 0.0413(3) 1.1543(2) 0.6156(2) 0.0694(6) Uani d . 1 . .
    H H10A -0.0632 1.1674 0.6207 0.104 Uiso calc R 1 . .
    H H10B 0.0682 1.2102 0.5311 0.104 Uiso calc R 1 . .
    H H10C 0.0740 1.1815 0.6882 0.104 Uiso calc R 1 . .
    C C11 -0.0097(3) 0.9152(2) 0.8436(2) 0.0766(7) Uani d . 1 . .
    H H11A 0.0614 0.9019 0.9107 0.115 Uiso calc R 1 . .
    H H11B -0.0653 0.8454 0.8721 0.115 Uiso calc R 1 . .
    H H11C -0.0744 1.0060 0.8315 0.115 Uiso calc R 1 . .
    C C12 0.3968(2) 0.9674(2) 0.3840(2) 0.0576(5) Uani d . 1 . .
    H H12 0.4319 0.8714 0.4143 0.069 Uiso calc R 1 . .
    C C13 0.4664(2) 1.0443(2) 0.26651(18) 0.0522(5) Uani d . 1 . .
    C C14 0.4270(2) 1.1868(2) 0.2223(2) 0.0606(5) Uani d . 1 . .
    H H14 0.3570 1.2371 0.2703 0.073 Uiso calc R 1 . .
    C C15 0.4889(2) 1.2563(2) 0.1090(2) 0.0617(5) Uani d . 1 . .
    H H15 0.4606 1.3530 0.0806 0.074 Uiso calc R 1 . .
    C C16 0.5932(2) 1.1835(2) 0.0365(2) 0.0551(5) Uani d . 1 . .
    C C17 0.6358(2) 1.0411(2) 0.0823(2) 0.0676(6) Uani d . 1 . .
    H H17 0.7082 0.9911 0.0360 0.081 Uiso calc R 1 . .
    C C18 0.5727(2) 0.9720(2) 0.1956(2) 0.0664(6) Uani d . 1 . .
    H H18 0.6020 0.8754 0.2249 0.080 Uiso calc R 1 . .
    C C19 0.6566(2) 1.2541(2) -0.0908(2) 0.0661(6) Uani d . 1 . .
    C C20 0.7092(17) 0.5482(6) 0.5150(11) 0.0959(17) Uani d PD 0.675(3) A 1
    H H20A 0.7486 0.6294 0.4951 0.144 Uiso calc PR 0.675(3) A 1
    H H20B 0.6493 0.5533 0.4416 0.144 Uiso calc PR 0.675(3) A 1
    H H20C 0.7880 0.4663 0.5272 0.144 Uiso calc PR 0.675(3) A 1
    O O4 0.6226(3) 0.5419(3) 0.6354(3) 0.0911(8) Uani d PD 0.675(3) A 1
    H H4 0.5415 0.5945 0.6178 0.137 Uiso calc PR 0.675(3) A 1
    C C20' 0.695(4) 0.5868(14) 0.518(3) 0.0959(17) Uani d PD 0.325(3) A 2
    H H20D 0.6472 0.6532 0.5675 0.144 Uiso calc PR 0.325(3) A 2
    H H20E 0.6467 0.6086 0.4334 0.144 Uiso calc PR 0.325(3) A 2
    H H20F 0.7954 0.5904 0.5026 0.144 Uiso calc PR 0.325(3) A 2
    O O4' 0.6863(6) 0.4500(6) 0.5942(6) 0.0911(8) Uani d PD 0.325(3) A 2
    H H4' 0.7677 0.3971 0.5977 0.137 Uiso calc PR 0.325(3) A 2
_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 C7 . 1.236(2) ?
    O2 C19 . 1.294(3) ?
    O2 H2 . 0.82 ?
    O3 C19 . 1.176(2) ?
    N1 C7 . 1.385(2) ?
    N1 N2 . 1.389(2) ?
    N1 C1 . 1.419(2) ?
    N2 C9 . 1.346(2) ?
    N2 C11 . 1.451(2) ?
    N3 C12 . 1.268(2) ?
    N3 C8 . 1.387(2) ?
    C1 C6 . 1.369(3) ?
    C1 C2 . 1.371(3) ?
    C2 C3 . 1.375(3) ?
    C2 H2A . 0.93 ?
    C3 C4 . 1.359(4) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.363(4) ?
    C4 H4A . 0.93 ?
    C5 C6 . 1.364(3) ?
    C5 H5 . 0.93 ?
    C6 H6 . 0.93 ?
    C7 C8 . 1.422(3) ?
    C8 C9 . 1.365(3) ?
    C9 C10 . 1.475(3) ?
    C10 H10A . 0.96 ?
    C10 H10B . 0.96 ?
    C10 H10C . 0.96 ?
    C11 H11A . 0.96 ?
    C11 H11B . 0.96 ?
    C11 H11C . 0.96 ?
    C12 C13 . 1.463(3) ?
    C12 H12 . 0.93 ?
    C13 C14 . 1.371(3) ?
    C13 C18 . 1.378(3) ?
    C14 C15 . 1.367(3) ?
    C14 H14 . 0.93 ?
    C15 C16 . 1.381(3) ?
    C15 H15 . 0.93 ?
    C16 C17 . 1.372(3) ?
    C16 C19 . 1.479(3) ?
    C17 C18 . 1.371(3) ?
    C17 H17 . 0.93 ?
    C18 H18 . 0.93 ?
    C20 O4 . 1.429(8) ?
    C20 H20A . 0.96 ?
    C20 H20B . 0.96 ?
    C20 H20C . 0.96 ?
    O4 H4 . 0.82 ?
    C20' O4' . 1.429(10) ?
    C20' H20D . 0.96 ?
    C20' H20E . 0.96 ?
    C20' H20F . 0.96 ?
    O4' H4' . 0.82 ?
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
    C19 O2 H2 . . 109.5 ?
    C7 N1 N2 . . 108.78(15) ?
    C7 N1 C1 . . 124.39(17) ?
    N2 N1 C1 . . 120.30(15) ?
    C9 N2 N1 . . 107.88(15) ?
    C9 N2 C11 . . 125.73(17) ?
    N1 N2 C11 . . 117.89(16) ?
    C12 N3 C8 . . 119.29(17) ?
    C6 C1 C2 . . 120.7(2) ?
    C6 C1 N1 . . 120.82(19) ?
    C2 C1 N1 . . 118.50(19) ?
    C1 C2 C3 . . 118.9(2) ?
    C1 C2 H2A . . 120.5 ?
    C3 C2 H2A . . 120.5 ?
    C4 C3 C2 . . 120.7(2) ?
    C4 C3 H3 . . 119.6 ?
    C2 C3 H3 . . 119.6 ?
    C3 C4 C5 . . 119.6(2) ?
    C3 C4 H4A . . 120.2 ?
    C5 C4 H4A . . 120.2 ?
    C4 C5 C6 . . 120.9(2) ?
    C4 C5 H5 . . 119.6 ?
    C6 C5 H5 . . 119.6 ?
    C5 C6 C1 . . 119.2(2) ?
    C5 C6 H6 . . 120.4 ?
    C1 C6 H6 . . 120.4 ?
    O1 C7 N1 . . 122.49(18) ?
    O1 C7 C8 . . 132.01(18) ?
    N1 C7 C8 . . 105.46(16) ?
    C9 C8 N3 . . 123.20(17) ?
    C9 C8 C7 . . 107.92(16) ?
    N3 C8 C7 . . 128.80(17) ?
    N2 C9 C8 . . 109.54(17) ?
    N2 C9 C10 . . 121.53(17) ?
    C8 C9 C10 . . 128.90(18) ?
    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 ?
    N3 C12 C13 . . 121.75(19) ?
    N3 C12 H12 . . 119.1 ?
    C13 C12 H12 . . 119.1 ?
    C14 C13 C18 . . 118.48(18) ?
    C14 C13 C12 . . 122.08(18) ?
    C18 C13 C12 . . 119.43(18) ?
    C15 C14 C13 . . 121.16(19) ?
    C15 C14 H14 . . 119.4 ?
    C13 C14 H14 . . 119.4 ?
    C14 C15 C16 . . 120.27(19) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C17 C16 C15 . . 118.79(18) ?
    C17 C16 C19 . . 119.29(18) ?
    C15 C16 C19 . . 121.90(18) ?
    C18 C17 C16 . . 120.62(18) ?
    C18 C17 H17 . . 119.7 ?
    C16 C17 H17 . . 119.7 ?
    C17 C18 C13 . . 120.65(19) ?
    C17 C18 H18 . . 119.7 ?
    C13 C18 H18 . . 119.7 ?
    O3 C19 O2 . . 122.4(2) ?
    O3 C19 C16 . . 124.0(2) ?
    O2 C19 C16 . . 113.67(18) ?
    O4' C20' H20D . . 109.5 ?
    O4' C20' H20E . . 109.5 ?
    H20D C20' H20E . . 109.5 ?
    O4' C20' H20F . . 109.5 ?
    H20D C20' H20F . . 109.5 ?
    H20E C20' H20F . . 109.5 ?
    C20' O4' H4' . . 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
    C7 N1 N2 C9 . . . . -6.8(2) ?
    C1 N1 N2 C9 . . . . -159.65(17) ?
    C7 N1 N2 C11 . . . . -156.69(18) ?
    C1 N1 N2 C11 . . . . 50.5(3) ?
    C7 N1 C1 C6 . . . . -113.7(2) ?
    N2 N1 C1 C6 . . . . 34.8(3) ?
    C7 N1 C1 C2 . . . . 64.5(3) ?
    N2 N1 C1 C2 . . . . -147.07(18) ?
    C6 C1 C2 C3 . . . . 1.4(3) ?
    N1 C1 C2 C3 . . . . -176.81(19) ?
    C1 C2 C3 C4 . . . . -1.6(4) ?
    C2 C3 C4 C5 . . . . 0.3(4) ?
    C3 C4 C5 C6 . . . . 1.3(4) ?
    C4 C5 C6 C1 . . . . -1.6(4) ?
    C2 C1 C6 C5 . . . . 0.2(3) ?
    N1 C1 C6 C5 . . . . 178.3(2) ?
    N2 N1 C7 O1 . . . . -172.90(18) ?
    C1 N1 C7 O1 . . . . -21.4(3) ?
    N2 N1 C7 C8 . . . . 4.9(2) ?
    C1 N1 C7 C8 . . . . 156.37(17) ?
    C12 N3 C8 C9 . . . . -179.22(18) ?
    C12 N3 C8 C7 . . . . -3.0(3) ?
    O1 C7 C8 C9 . . . . 176.2(2) ?
    N1 C7 C8 C9 . . . . -1.3(2) ?
    O1 C7 C8 N3 . . . . -0.5(4) ?
    N1 C7 C8 N3 . . . . -177.98(17) ?
    N1 N2 C9 C8 . . . . 6.0(2) ?
    C11 N2 C9 C8 . . . . 152.85(19) ?
    N1 N2 C9 C10 . . . . -172.21(17) ?
    C11 N2 C9 C10 . . . . -25.3(3) ?
    N3 C8 C9 N2 . . . . 173.99(16) ?
    C7 C8 C9 N2 . . . . -2.9(2) ?
    N3 C8 C9 C10 . . . . -8.0(3) ?
    C7 C8 C9 C10 . . . . 175.10(19) ?
    C8 N3 C12 C13 . . . . 178.87(16) ?
    N3 C12 C13 C14 . . . . 4.7(3) ?
    N3 C12 C13 C18 . . . . -173.90(19) ?
    C18 C13 C14 C15 . . . . 1.4(3) ?
    C12 C13 C14 C15 . . . . -177.15(18) ?
    C13 C14 C15 C16 . . . . -0.1(3) ?
    C14 C15 C16 C17 . . . . -1.7(3) ?
    C14 C15 C16 C19 . . . . 176.52(19) ?
    C15 C16 C17 C18 . . . . 2.0(3) ?
    C19 C16 C17 C18 . . . . -176.2(2) ?
    C16 C17 C18 C13 . . . . -0.7(4) ?
    C14 C13 C18 C17 . . . . -1.0(3) ?
    C12 C13 C18 C17 . . . . 177.58(19) ?
    C17 C16 C19 O3 . . . . -15.6(4) ?
    C15 C16 C19 O3 . . . . 166.2(3) ?
    C17 C16 C19 O2 . . . . 165.5(2) ?
    C15 C16 C19 O2 . . . . -12.7(3) ?
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
    O2 H2 O4 1_564 0.82 1.75 2.513(3) 153
    O2 H2 O4' 1_564 0.82 2.00 2.796(6) 165
    O4 H4 O1 . 0.82 1.89 2.712(3) 177
    C11 H11C O3 1_456 0.96 2.27 3.209(3) 166
    C12 H12 O1 . 0.93 2.26 2.966(3) 132
