##############################################################################
###                                                                        ###
###        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                #
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##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2006-07-25
_journal_date_accepted     2006-07-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      9
_journal_page_first     o3676
_journal_page_last     o3677
_journal_paper_category     EO
_journal_coeditor_code     CI2132
_publ_contact_author_name     'Hua-Zheng Yang'
_publ_contact_author_address
;
State Key Laboratory of  Enlemento-Organic Chemistry
Nankai University
Tianjin 300071
Peoples' Republic of China
;
_publ_contact_author_email     zyq8165@nankai.edu.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     '086-022-23506567'
_publ_section_title
;
(E)-1,3-Dimethyl-5-p-tolyloxy-1H-pyrazole-4-carbaldehyde
O-(6-chloropyridazin-3-yl)oxime
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Fang-Zhong Hu' .
;
State Key Laboratory of  Elemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'Yong-Qiang Chang' .
;
State Key Laboratory of Elemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'Yong-Quan Zhu' .
;
State Key Laboratory of Elemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'XiaO Miao Zou' .
;
State Key Laboratory of Elemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'Hua-Zheng Yang' .
;
State Key Laboratory of Elemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
data_I
_chemical_name_systematic
;
(E)-1,3-Dimethyl-5-p-tolyloxy-1H-pyrazole-4-carbaldehyde
O-(6-chloropyridazin-3-yl)oxime
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H18 Cl N5 O2'
_chemical_formula_sum     'C18 H18 Cl N5 O2'
_chemical_formula_iupac     'C18 H18 Cl N5 O2'
_chemical_formula_weight     371.82
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_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     14.866(3)
_cell_length_b     10.499(2)
_cell_length_c     24.121(5)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3764.7(12)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2639
_cell_measurement_theta_min     2.52
_cell_measurement_theta_max     20.76
_cell_measurement_temperature     294(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.312
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1552
_exptl_absorpt_coefficient_mu     0.225
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9355
_exptl_absorpt_correction_T_max     0.9564
_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     17909
_diffrn_reflns_av_R_equivalents     0.0696
_diffrn_reflns_av_sigmaI/netI     0.0494
_diffrn_reflns_theta_min     1.69
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     28
_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     3320
_reflns_number_gt     1606
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1378
_refine_ls_R_factor_gt     0.0554
_refine_ls_wR_factor_gt     0.1368
_refine_ls_wR_factor_ref     0.1867
_refine_ls_goodness_of_fit_ref     1.016
_refine_ls_restrained_S_all     1.016
_refine_ls_number_reflns     3320
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0543P)²+6.5016P] 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     0.395
_refine_diff_density_min     -0.240
_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'
    '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'
_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
    Cl Cl1 0.17485(9) 0.73527(13) 0.17777(5) 0.0766(5) Uani d . 1 . .
    O O1 0.5795(2) 1.1202(3) 0.43031(12) 0.0709(10) Uani d . 1 . .
    O O2 0.2640(2) 0.9383(3) 0.42778(13) 0.0683(9) Uani d . 1 . .
    N N1 0.6521(3) 0.9235(5) 0.44178(15) 0.0686(12) Uani d . 1 . .
    N N2 0.6334(3) 0.7970(5) 0.44903(16) 0.0728(12) Uani d . 1 . .
    N N3 0.3471(3) 0.8705(4) 0.42853(15) 0.0608(10) Uani d . 1 . .
    N N4 0.1682(3) 0.9010(4) 0.32123(17) 0.0668(11) Uani d . 1 . .
    N N5 0.1653(3) 0.8747(4) 0.26632(17) 0.0675(11) Uani d . 1 . .
    C C1 0.5608(3) 1.3025(5) 0.3736(2) 0.0691(14) Uani d . 1 . .
    H H1 0.5525 1.3505 0.4056 0.083 Uiso calc R 1 . .
    C C2 0.5587(3) 1.3599(5) 0.3219(3) 0.0747(15) Uani d . 1 . .
    H H2 0.5494 1.4473 0.3195 0.090 Uiso calc R 1 . .
    C C3 0.5702(3) 1.2902(5) 0.2738(2) 0.0640(13) Uani d . 1 . .
    C C4 0.5683(4) 1.3552(6) 0.2186(2) 0.0928(19) Uani d . 1 . .
    H H4A 0.5322 1.4308 0.2210 0.139 Uiso calc R 1 . .
    H H4B 0.5430 1.2988 0.1914 0.139 Uiso calc R 1 . .
    H H4C 0.6284 1.3777 0.2079 0.139 Uiso calc R 1 . .
    C C5 0.5841(3) 1.1619(5) 0.2789(2) 0.0635(13) Uani d . 1 . .
    H H5 0.5912 1.1135 0.2469 0.076 Uiso calc R 1 . .
    C C6 0.5879(3) 1.1011(4) 0.32981(18) 0.0579(12) Uani d . 1 . .
    H H6 0.5986 1.0140 0.3320 0.069 Uiso calc R 1 . .
    C C7 0.5755(3) 1.1720(4) 0.37690(19) 0.0541(12) Uani d . 1 . .
    C C8 0.5767(3) 0.9915(5) 0.43484(17) 0.0571(12) Uani d . 1 . .
    C C9 0.5046(3) 0.9092(4) 0.43662(16) 0.0516(11) Uani d . 1 . .
    C C10 0.5439(4) 0.7891(5) 0.44540(18) 0.0635(13) Uani d . 1 . .
    C C11 0.4977(4) 0.6632(5) 0.4506(2) 0.0941(19) Uani d . 1 . .
    H H11A 0.5399 0.6003 0.4631 0.141 Uiso calc R 1 . .
    H H11B 0.4739 0.6384 0.4152 0.141 Uiso calc R 1 . .
    H H11C 0.4494 0.6701 0.4769 0.141 Uiso calc R 1 . .
    C C12 0.7454(4) 0.9681(7) 0.4402(2) 0.102(2) Uani d . 1 . .
    H H12A 0.7703 0.9523 0.4042 0.152 Uiso calc R 1 . .
    H H12B 0.7800 0.9235 0.4676 0.152 Uiso calc R 1 . .
    H H12C 0.7471 1.0578 0.4479 0.152 Uiso calc R 1 . .
    C C13 0.4117(3) 0.9491(5) 0.43231(16) 0.0558(12) Uani d . 1 . .
    H H13 0.3988 1.0358 0.4323 0.067 Uiso calc R 1 . .
    C C14 0.1931(3) 0.8492(5) 0.4165(2) 0.0762(16) Uani d . 1 . .
    H H14A 0.1358 0.8876 0.4259 0.091 Uiso calc R 1 . .
    H H14B 0.2010 0.7745 0.4397 0.091 Uiso calc R 1 . .
    C C15 0.1918(3) 0.8089(5) 0.35613(19) 0.0553(12) Uani d . 1 . .
    C C16 0.2131(3) 0.6879(5) 0.3385(2) 0.0705(15) Uani d . 1 . .
    H H16 0.2299 0.6256 0.3639 0.085 Uiso calc R 1 . .
    C C17 0.2092(3) 0.6607(5) 0.2830(2) 0.0734(15) Uani d . 1 . .
    H H17 0.2233 0.5805 0.2691 0.088 Uiso calc R 1 . .
    C C18 0.1832(3) 0.7589(5) 0.2490(2) 0.0593(12) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl1 0.0850(9) 0.0806(9) 0.0643(8) 0.0162(8) -0.0140(7) -0.0098(7)
    O1 0.090(3) 0.072(2) 0.051(2) -0.015(2) 0.0027(18) -0.0099(18)
    O2 0.055(2) 0.083(2) 0.067(2) 0.0041(19) -0.0013(17) 0.0008(19)
    N1 0.061(3) 0.096(4) 0.049(2) 0.006(3) 0.004(2) -0.005(2)
    N2 0.071(3) 0.092(4) 0.056(3) 0.022(3) 0.008(2) 0.006(2)
    N3 0.059(3) 0.068(3) 0.055(2) 0.002(2) 0.001(2) 0.000(2)
    N4 0.077(3) 0.055(2) 0.068(3) -0.001(2) -0.012(2) 0.010(2)
    N5 0.085(3) 0.054(3) 0.064(3) 0.005(2) -0.017(2) 0.010(2)
    C1 0.063(3) 0.057(3) 0.087(4) 0.001(3) 0.009(3) -0.017(3)
    C2 0.071(4) 0.053(3) 0.101(4) 0.009(3) 0.004(3) 0.003(3)
    C3 0.050(3) 0.060(3) 0.081(4) 0.001(3) -0.002(3) 0.014(3)
    C4 0.081(4) 0.094(4) 0.104(5) 0.010(3) 0.000(3) 0.035(4)
    C5 0.071(3) 0.064(3) 0.056(3) -0.005(3) 0.004(3) 0.002(3)
    C6 0.072(3) 0.050(3) 0.052(3) -0.010(2) 0.002(2) -0.002(2)
    C7 0.054(3) 0.058(3) 0.049(3) -0.011(2) -0.001(2) -0.004(2)
    C8 0.067(3) 0.065(3) 0.039(3) 0.001(3) 0.004(2) -0.004(2)
    C9 0.055(3) 0.060(3) 0.040(2) 0.001(2) 0.002(2) -0.002(2)
    C10 0.075(4) 0.071(4) 0.044(3) 0.010(3) 0.007(2) 0.008(2)
    C11 0.124(5) 0.068(4) 0.090(4) 0.009(4) 0.011(4) 0.019(3)
    C12 0.060(4) 0.158(6) 0.087(4) -0.009(4) 0.006(3) -0.020(4)
    C13 0.068(3) 0.058(3) 0.041(3) 0.002(3) -0.001(2) 0.003(2)
    C14 0.057(3) 0.097(4) 0.075(4) -0.015(3) 0.007(3) 0.015(3)
    C15 0.043(3) 0.058(3) 0.064(3) -0.008(2) 0.003(2) 0.016(3)
    C16 0.064(3) 0.054(3) 0.094(4) 0.003(3) 0.001(3) 0.034(3)
    C17 0.080(4) 0.059(3) 0.082(4) 0.002(3) 0.001(3) 0.008(3)
    C18 0.058(3) 0.051(3) 0.068(3) 0.000(2) -0.007(2) 0.009(3)
_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 C18 . 1.741(5) no
    O1 C8 . 1.356(5) no
    O1 C7 . 1.399(5) no
    O2 N3 . 1.426(5) no
    O2 C14 . 1.434(5) no
    N1 C8 . 1.340(6) no
    N1 N2 . 1.368(6) no
    N1 C12 . 1.465(6) no
    N2 C10 . 1.335(6) no
    N3 C13 . 1.271(5) no
    N4 C15 . 1.329(5) no
    N4 N5 . 1.353(5) no
    N5 C18 . 1.312(6) no
    C1 C2 . 1.385(7) no
    C1 C7 . 1.390(6) no
    C1 H1 . 0.93 no
    C2 C3 . 1.383(7) no
    C2 H2 . 0.93 no
    C3 C5 . 1.369(6) no
    C3 C4 . 1.497(7) no
    C4 H4A . 0.96 no
    C4 H4B . 0.96 no
    C4 H4C . 0.96 no
    C5 C6 . 1.385(6) no
    C5 H5 . 0.93 no
    C6 C7 . 1.370(6) no
    C6 H6 . 0.93 no
    C8 C9 . 1.377(6) no
    C9 C10 . 1.406(6) no
    C9 C13 . 1.447(6) no
    C10 C11 . 1.495(7) no
    C11 H11A . 0.96 no
    C11 H11B . 0.96 no
    C11 H11C . 0.96 no
    C12 H12A . 0.96 no
    C12 H12B . 0.96 no
    C12 H12C . 0.96 no
    C13 H13 . 0.93 no
    C14 C15 . 1.517(6) no
    C14 H14A . 0.97 no
    C14 H14B . 0.97 no
    C15 C16 . 1.376(7) no
    C16 C17 . 1.372(7) no
    C16 H16 . 0.93 no
    C17 C18 . 1.373(6) no
    C17 H17 . 0.93 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
    C8 O1 C7 . . 117.4(3) no
    N3 O2 C14 . . 108.2(4) no
    C8 N1 N2 . . 111.3(4) no
    C8 N1 C12 . . 128.2(5) no
    N2 N1 C12 . . 120.4(5) no
    C10 N2 N1 . . 104.7(4) no
    C13 N3 O2 . . 109.4(4) no
    C15 N4 N5 . . 118.7(4) no
    C18 N5 N4 . . 119.6(4) no
    C2 C1 C7 . . 119.0(5) no
    C2 C1 H1 . . 120.5 no
    C7 C1 H1 . . 120.5 no
    C3 C2 C1 . . 121.5(5) no
    C3 C2 H2 . . 119.3 no
    C1 C2 H2 . . 119.3 no
    C5 C3 C2 . . 117.6(5) no
    C5 C3 C4 . . 122.2(5) no
    C2 C3 C4 . . 120.2(5) 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
    C3 C5 C6 . . 122.7(5) no
    C3 C5 H5 . . 118.7 no
    C6 C5 H5 . . 118.7 no
    C7 C6 C5 . . 118.6(4) no
    C7 C6 H6 . . 120.7 no
    C5 C6 H6 . . 120.7 no
    C6 C7 C1 . . 120.6(5) no
    C6 C7 O1 . . 123.1(4) no
    C1 C7 O1 . . 116.3(4) no
    N1 C8 O1 . . 121.0(5) no
    N1 C8 C9 . . 108.2(4) no
    O1 C8 C9 . . 130.7(5) no
    C8 C9 C10 . . 104.1(4) no
    C8 C9 C13 . . 123.9(5) no
    C10 C9 C13 . . 131.9(5) no
    N2 C10 C9 . . 111.6(5) no
    N2 C10 C11 . . 120.5(5) no
    C9 C10 C11 . . 127.9(5) no
    C10 C11 H11A . . 109.5 no
    C10 C11 H11B . . 109.5 no
    H11A C11 H11B . . 109.5 no
    C10 C11 H11C . . 109.5 no
    H11A C11 H11C . . 109.5 no
    H11B C11 H11C . . 109.5 no
    N1 C12 H12A . . 109.5 no
    N1 C12 H12B . . 109.5 no
    H12A C12 H12B . . 109.5 no
    N1 C12 H12C . . 109.5 no
    H12A C12 H12C . . 109.5 no
    H12B C12 H12C . . 109.5 no
    N3 C13 C9 . . 122.6(4) no
    N3 C13 H13 . . 118.7 no
    C9 C13 H13 . . 118.7 no
    O2 C14 C15 . . 111.9(4) no
    O2 C14 H14A . . 109.2 no
    C15 C14 H14A . . 109.2 no
    O2 C14 H14B . . 109.2 no
    C15 C14 H14B . . 109.2 no
    H14A C14 H14B . . 107.9 no
    N4 C15 C16 . . 122.5(5) no
    N4 C15 C14 . . 114.2(5) no
    C16 C15 C14 . . 123.4(5) no
    C17 C16 C15 . . 118.9(5) no
    C17 C16 H16 . . 120.6 no
    C15 C16 H16 . . 120.6 no
    C16 C17 C18 . . 116.1(5) no
    C16 C17 H17 . . 122.0 no
    C18 C17 H17 . . 122.0 no
    N5 C18 C17 . . 124.2(5) no
    N5 C18 Cl1 . . 115.6(4) no
    C17 C18 Cl1 . . 120.1(4) 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
    C8 N1 N2 C10 . . . . 1.0(5) no
    C12 N1 N2 C10 . . . . -176.7(4) no
    C14 O2 N3 C13 . . . . 172.9(4) no
    C15 N4 N5 C18 . . . . 1.9(7) no
    C7 C1 C2 C3 . . . . 0.5(8) no
    C1 C2 C3 C5 . . . . -0.2(7) no
    C1 C2 C3 C4 . . . . -179.5(5) no
    C2 C3 C5 C6 . . . . -0.8(7) no
    C4 C3 C5 C6 . . . . 178.6(4) no
    C3 C5 C6 C7 . . . . 1.3(7) no
    C5 C6 C7 C1 . . . . -0.9(7) no
    C5 C6 C7 O1 . . . . -178.9(4) no
    C2 C1 C7 C6 . . . . 0.1(7) no
    C2 C1 C7 O1 . . . . 178.2(4) no
    C8 O1 C7 C6 . . . . -14.1(6) no
    C8 O1 C7 C1 . . . . 167.8(4) no
    N2 N1 C8 O1 . . . . 176.0(4) no
    C12 N1 C8 O1 . . . . -6.5(7) no
    N2 N1 C8 C9 . . . . -0.8(5) no
    C12 N1 C8 C9 . . . . 176.7(4) no
    C7 O1 C8 N1 . . . . 99.2(5) no
    C7 O1 C8 C9 . . . . -84.8(6) no
    N1 C8 C9 C10 . . . . 0.3(5) no
    O1 C8 C9 C10 . . . . -176.1(4) no
    N1 C8 C9 C13 . . . . 178.0(4) no
    O1 C8 C9 C13 . . . . 1.6(7) no
    N1 N2 C10 C9 . . . . -0.8(5) no
    N1 N2 C10 C11 . . . . 179.3(4) no
    C8 C9 C10 N2 . . . . 0.3(5) no
    C13 C9 C10 N2 . . . . -177.2(4) no
    C8 C9 C10 C11 . . . . -179.7(5) no
    C13 C9 C10 C11 . . . . 2.8(8) no
    O2 N3 C13 C9 . . . . 177.1(3) no
    C8 C9 C13 N3 . . . . 172.8(4) no
    C10 C9 C13 N3 . . . . -10.2(7) no
    N3 O2 C14 C15 . . . . -74.7(5) no
    N5 N4 C15 C16 . . . . -0.2(7) no
    N5 N4 C15 C14 . . . . 179.8(4) no
    O2 C14 C15 N4 . . . . -68.3(5) no
    O2 C14 C15 C16 . . . . 111.7(5) no
    N4 C15 C16 C17 . . . . -0.6(7) no
    C14 C15 C16 C17 . . . . 179.5(4) no
    C15 C16 C17 C18 . . . . -0.3(7) no
    N4 N5 C18 C17 . . . . -3.0(8) no
    N4 N5 C18 Cl1 . . . . 178.6(3) no
    C16 C17 C18 N5 . . . . 2.2(8) no
    C16 C17 C18 Cl1 . . . . -179.5(4) 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
    C16 H16 O2 8_655 0.93 2.50 3.409(6) 166
