##############################################################################
###                                                                        ###
###        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     'SHELXL-97'
_journal_date_recd_electronic     2006-04-21
_journal_date_accepted     2006-05-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      6
_journal_page_first     o2471
_journal_page_last     o2472
_journal_paper_category     EO
_journal_coeditor_code     FL2024
_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     ldy351@sohu.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '086-022-23506567'
_publ_section_title
;\
(E)-5-(3,5-Dimethylphenoxy)-1,3-dimethyl-1H-pyrazole-4-\
carbaldehyde O-(2-chloropyrimidin-4-yl)oxime
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Xiao-Mao Zou' .
;
State Key Laboratory of  Enlemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'Da-yong Lin' .
;
State Key Laboratory of Enlemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'Jiang Pei' .
;
State Key Laboratory of Enlemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'Chao-Qiang Wang' .
;
State Key Laboratory of Enlemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
    'Hua-Zheng Yang' .
;
State Key Laboratory of Enlemento-Organic Chemistry
Nankai University
Tianjin 300071
People's Republic of China
;
data_I
_chemical_name_systematic
;
(E)-5-(3,5-Dimethylphenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde
O-(2-chloropyrimidin-4-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     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     8.217(2)
_cell_length_b     8.4391(15)
_cell_length_c     30.674(5)
_cell_angle_alpha     93.150(10)
_cell_angle_beta     90.342(3)
_cell_angle_gamma     118.958(3)
_cell_volume     1857.0(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2954
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     23.28
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.330
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     776
_exptl_absorpt_coefficient_mu     0.228
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.8945
_exptl_absorpt_correction_T_max     0.9558
_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     9445
_diffrn_reflns_av_R_equivalents     0.0258
_diffrn_reflns_av_sigmaI/netI     0.0553
_diffrn_reflns_theta_min     0.67
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -36
_diffrn_reflns_limit_l_max     36
_diffrn_standards_number     .
_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     6481
_reflns_number_gt     4096
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0885
_refine_ls_R_factor_gt     0.0501
_refine_ls_wR_factor_gt     0.1266
_refine_ls_wR_factor_ref     0.1461
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     6481
_refine_ls_number_parameters     478
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0725P)²+0.178P] 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     0.003
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.362
_refine_diff_density_min     -0.409
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.0153(15)
_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     SMART
_computing_data_reduction     'SAINT (Bruker,1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_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 0.51047(14) -0.49841(11) 0.39047(3) 0.0877(3) Uani d . 1 . .
    Cl Cl2 1.01971(16) -0.00577(15) 0.10191(3) 0.0924(4) Uani d . 1 . .
    O O1 0.8097(3) 0.1268(2) 0.35789(6) 0.0572(5) Uani d . 1 . .
    O O2 1.2226(3) 0.7954(3) 0.39136(6) 0.0516(5) Uani d . 1 . .
    O O3 0.6676(3) 0.2922(3) 0.14041(6) 0.0600(6) Uani d . 1 . .
    O O4 0.4006(3) 0.7109(2) 0.11986(6) 0.0596(6) Uani d . 1 . .
    N N1 0.4050(3) -0.3894(3) 0.32449(8) 0.0561(6) Uani d . 1 . .
    N N2 0.6599(3) -0.1664(3) 0.36949(7) 0.0501(6) Uani d . 1 . .
    N N3 0.8081(4) 0.2701(3) 0.33422(7) 0.0546(6) Uani d . 1 . .
    N N4 1.0988(4) 0.8888(3) 0.33576(7) 0.0527(6) Uani d . 1 . .
    N N5 0.9751(4) 0.8205(3) 0.30058(7) 0.0567(7) Uani d . 1 . .
    N N6 0.8249(4) -0.0782(3) 0.17097(8) 0.0590(7) Uani d . 1 . .
    N N7 0.8242(3) 0.1444(3) 0.12630(7) 0.0512(6) Uani d . 1 . .
    N N8 0.5251(4) 0.3016(3) 0.16579(7) 0.0548(6) Uani d . 1 . .
    N N9 0.1872(4) 0.6013(3) 0.17538(8) 0.0566(7) Uani d . 1 . .
    N N10 0.1335(4) 0.4805(3) 0.20755(7) 0.0575(7) Uani d . 1 . .
    C C1 0.5267(4) -0.3321(4) 0.35717(9) 0.0509(7) Uani d . 1 . .
    C C2 0.4193(4) -0.2547(4) 0.30039(9) 0.0569(8) Uani d . 1 . .
    H H2 0.3369 -0.2850 0.2766 0.068 Uiso calc R 1 . .
    C C3 0.5482(4) -0.0761(4) 0.30896(8) 0.0505(7) Uani d . 1 . .
    H H3 0.5543 0.0149 0.2921 0.061 Uiso calc R 1 . .
    C C4 0.6689(4) -0.0399(3) 0.34433(8) 0.0438(7) Uani d . 1 . .
    C C5 0.9364(4) 0.4201(4) 0.35133(9) 0.0491(7) Uani d . 1 . .
    H H5 1.0102 0.4178 0.3741 0.059 Uiso calc R 1 . .
    C C6 0.9725(4) 0.5930(3) 0.33697(8) 0.0437(7) Uani d . 1 . .
    C C7 0.8990(4) 0.6412(4) 0.30152(8) 0.0478(7) Uani d . 1 . .
    C C8 0.7566(5) 0.5202(4) 0.26745(10) 0.0692(9) Uani d . 1 . .
    H H8A 0.7343 0.5926 0.2477 0.104 Uiso calc R 1 . .
    H H8B 0.6429 0.4420 0.2811 0.104 Uiso calc R 1 . .
    H H8C 0.8007 0.4482 0.2516 0.104 Uiso calc R 1 . .
    C C9 1.2091(5) 1.0839(4) 0.34618(11) 0.0743(10) Uani d . 1 . .
    H H9A 1.2646 1.1058 0.3750 0.111 Uiso calc R 1 . .
    H H9B 1.1302 1.1382 0.3449 0.111 Uiso calc R 1 . .
    H H9C 1.3052 1.1361 0.3255 0.111 Uiso calc R 1 . .
    C C10 1.0995(4) 0.7572(3) 0.35770(8) 0.0425(6) Uani d . 1 . .
    C C11 1.1571(4) 0.7780(3) 0.43404(8) 0.0405(6) Uani d . 1 . .
    C C12 1.2726(4) 0.7712(3) 0.46568(8) 0.0445(7) Uani d . 1 . .
    H H12 1.3835 0.7743 0.4581 0.053 Uiso calc R 1 . .
    C C13 1.2223(4) 0.7597(4) 0.50890(9) 0.0472(7) Uani d . 1 . .
    C C14 1.3464(5) 0.7530(5) 0.54446(10) 0.0671(9) Uani d . 1 . .
    H H14A 1.4718 0.8052 0.5349 0.101 Uiso calc R 1 . .
    H H14B 1.3035 0.6290 0.5508 0.101 Uiso calc R 1 . .
    H H14C 1.3425 0.8203 0.5703 0.101 Uiso calc R 1 . .
    C C15 1.0546(4) 0.7529(4) 0.51870(9) 0.0525(7) Uani d . 1 . .
    H H15 1.0193 0.7435 0.5476 0.063 Uiso calc R 1 . .
    C C16 0.9380(4) 0.7595(4) 0.48698(9) 0.0494(7) Uani d . 1 . .
    C C17 0.7566(4) 0.7526(5) 0.49872(11) 0.0700(9) Uani d . 1 . .
    H H17A 0.6606 0.6283 0.4990 0.105 Uiso calc R 1 . .
    H H17B 0.7234 0.8126 0.4775 0.105 Uiso calc R 1 . .
    H H17C 0.7703 0.8123 0.5271 0.105 Uiso calc R 1 . .
    C C18 0.9913(4) 0.7731(3) 0.44373(8) 0.0449(7) Uani d . 1 . .
    H H18 0.9162 0.7788 0.4218 0.054 Uiso calc R 1 . .
    C C19 0.8722(4) 0.0238(4) 0.13744(9) 0.0510(7) Uani d . 1 . .
    C C20 0.7119(5) -0.0473(4) 0.19779(9) 0.0623(9) Uani d . 1 . .
    H H20 0.6748 -0.1118 0.2228 0.075 Uiso calc R 1 . .
    C C21 0.6488(4) 0.0720(4) 0.19063(9) 0.0536(8) Uani d . 1 . .
    H H21 0.5692 0.0886 0.2095 0.064 Uiso calc R 1 . .
    C C22 0.7111(4) 0.1665(4) 0.15354(8) 0.0452(7) Uani d . 1 . .
    C C23 0.4959(4) 0.4246(4) 0.15097(9) 0.0510(7) Uani d . 1 . .
    H H23 0.5667 0.4894 0.1282 0.061 Uiso calc R 1 . .
    C C24 0.3580(4) 0.4664(4) 0.16811(8) 0.0444(7) Uani d . 1 . .
    C C25 0.2358(4) 0.3993(4) 0.20276(8) 0.0470(7) Uani d . 1 . .
    C C26 0.2151(5) 0.2594(4) 0.23331(9) 0.0626(9) Uani d . 1 . .
    H H26A 0.1189 0.2412 0.2533 0.094 Uiso calc R 1 . .
    H H26B 0.3305 0.2997 0.2494 0.094 Uiso calc R 1 . .
    H H26C 0.1824 0.1472 0.2169 0.094 Uiso calc R 1 . .
    C C27 0.1006(6) 0.7148(5) 0.17064(13) 0.0889(12) Uani d . 1 . .
    H H27A 0.1854 0.8237 0.1573 0.133 Uiso calc R 1 . .
    H H27B 0.0704 0.7457 0.1989 0.133 Uiso calc R 1 . .
    H H27C -0.0109 0.6499 0.1526 0.133 Uiso calc R 1 . .
    C C28 0.3197(4) 0.5947(4) 0.15181(8) 0.0476(7) Uani d . 1 . .
    C C29 0.3528(4) 0.6416(3) 0.07602(8) 0.0441(7) Uani d . 1 . .
    C C30 0.4723(4) 0.7493(4) 0.04592(9) 0.0481(7) Uani d . 1 . .
    H H30 0.5769 0.8581 0.0550 0.058 Uiso calc R 1 . .
    C C31 0.4361(4) 0.6951(4) 0.00190(9) 0.0481(7) Uani d . 1 . .
    C C32 0.5628(5) 0.8117(5) -0.03216(10) 0.0700(9) Uani d . 1 . .
    H H32A 0.6436 0.9314 -0.0192 0.105 Uiso calc R 1 . .
    H H32B 0.4894 0.8187 -0.0557 0.105 Uiso calc R 1 . .
    H H32C 0.6363 0.7591 -0.0433 0.105 Uiso calc R 1 . .
    C C33 0.2784(4) 0.5310(4) -0.01017(9) 0.0506(7) Uani d . 1 . .
    H H33 0.2536 0.4929 -0.0396 0.061 Uiso calc R 1 . .
    C C34 0.1568(4) 0.4221(3) 0.02006(9) 0.0462(7) Uani d . 1 . .
    C C35 -0.0120(4) 0.2462(4) 0.00598(10) 0.0631(9) Uani d . 1 . .
    H H35A -0.0676 0.2609 -0.0200 0.095 Uiso calc R 1 . .
    H H35B -0.1001 0.2107 0.0288 0.095 Uiso calc R 1 . .
    H H35C 0.0234 0.1543 0.0002 0.095 Uiso calc R 1 . .
    C C36 0.1955(4) 0.4809(3) 0.06414(9) 0.0468(7) Uani d . 1 . .
    H H36 0.1155 0.4122 0.0853 0.056 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 C1 . 1.735(3) no
    Cl2 C19 . 1.731(3) no
    O1 C4 . 1.358(3) no
    O1 N3 . 1.450(3) yes
    O2 C10 . 1.352(3) no
    O2 C11 . 1.406(3) no
    O3 C22 . 1.352(3) no
    O3 N8 . 1.441(3) no
    O4 C28 . 1.359(3) no
    O4 C29 . 1.410(3) no
    N1 C1 . 1.306(4) no
    N1 C2 . 1.347(4) no
    N2 C1 . 1.323(3) no
    N2 C4 . 1.325(3) no
    N3 C5 . 1.272(3) yes
    N4 C10 . 1.332(3) yes
    N4 N5 . 1.371(3) yes
    N4 C9 . 1.459(4) no
    N5 C7 . 1.331(3) yes
    N6 C19 . 1.314(3) no
    N6 C20 . 1.351(4) no
    N7 C19 . 1.317(3) no
    N7 C22 . 1.325(3) no
    N8 C23 . 1.278(3) no
    N9 C28 . 1.332(4) no
    N9 N10 . 1.374(3) no
    N9 C27 . 1.456(4) no
    N10 C25 . 1.321(3) no
    C2 C3 . 1.368(4) no
    C2 H2 . 0.9300 no
    C3 C4 . 1.382(4) no
    C3 H3 . 0.9300 no
    C5 C6 . 1.437(4) yes
    C5 H5 . 0.9300 no
    C6 C10 . 1.382(4) yes
    C6 C7 . 1.411(4) yes
    C7 C8 . 1.488(4) no
    C8 H8A . 0.9600 no
    C8 H8B . 0.9600 no
    C8 H8C . 0.9600 no
    C9 H9A . 0.9600 no
    C9 H9B . 0.9600 no
    C9 H9C . 0.9600 no
    C11 C12 . 1.376(4) no
    C11 C18 . 1.377(4) no
    C12 C13 . 1.385(4) no
    C12 H12 . 0.9300 no
    C13 C15 . 1.386(4) no
    C13 C14 . 1.511(4) no
    C14 H14A . 0.9600 no
    C14 H14B . 0.9600 no
    C14 H14C . 0.9600 no
    C15 C16 . 1.383(4) no
    C15 H15 . 0.9300 no
    C16 C18 . 1.393(4) no
    C16 C17 . 1.510(4) no
    C17 H17A . 0.9600 no
    C17 H17B . 0.9600 no
    C17 H17C . 0.9600 no
    C18 H18 . 0.9300 no
    C20 C21 . 1.364(4) no
    C20 H20 . 0.9300 no
    C21 C22 . 1.380(4) no
    C21 H21 . 0.9300 no
    C23 C24 . 1.435(4) no
    C23 H23 . 0.9300 no
    C24 C28 . 1.381(4) no
    C24 C25 . 1.410(4) no
    C25 C26 . 1.494(4) no
    C26 H26A . 0.9600 no
    C26 H26B . 0.9600 no
    C26 H26C . 0.9600 no
    C27 H27A . 0.9600 no
    C27 H27B . 0.9600 no
    C27 H27C . 0.9600 no
    C29 C30 . 1.372(4) no
    C29 C36 . 1.373(4) no
    C30 C31 . 1.384(4) no
    C30 H30 . 0.9300 no
    C31 C33 . 1.391(4) no
    C31 C32 . 1.509(4) no
    C32 H32A . 0.9600 no
    C32 H32B . 0.9600 no
    C32 H32C . 0.9600 no
    C33 C34 . 1.385(4) no
    C33 H33 . 0.9300 no
    C34 C36 . 1.394(4) no
    C34 C35 . 1.498(4) no
    C35 H35A . 0.9600 no
    C35 H35B . 0.9600 no
    C35 H35C . 0.9600 no
    C36 H36 . 0.9300 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
    C4 O1 N3 . . 112.4(2) yes
    C10 O2 C11 . . 118.1(2) no
    C22 O3 N8 . . 112.9(2) no
    C28 O4 C29 . . 118.1(2) no
    C1 N1 C2 . . 113.1(2) no
    C1 N2 C4 . . 113.8(2) no
    C5 N3 O1 . . 107.2(2) yes
    C10 N4 N5 . . 111.8(2) yes
    C10 N4 C9 . . 127.0(3) yes
    N5 N4 C9 . . 121.2(2) no
    C7 N5 N4 . . 104.8(2) yes
    C19 N6 C20 . . 112.4(2) no
    C19 N7 C22 . . 114.4(2) no
    C23 N8 O3 . . 107.8(2) no
    C28 N9 N10 . . 111.1(2) no
    C28 N9 C27 . . 128.7(3) no
    N10 N9 C27 . . 120.3(3) no
    C25 N10 N9 . . 105.1(2) no
    N1 C1 N2 . . 130.4(3) no
    N1 C1 Cl1 . . 115.3(2) no
    N2 C1 Cl1 . . 114.3(2) no
    N1 C2 C3 . . 123.7(3) no
    N1 C2 H2 . . 118.1 no
    C3 C2 H2 . . 118.1 no
    C2 C3 C4 . . 115.5(3) no
    C2 C3 H3 . . 122.3 no
    C4 C3 H3 . . 122.3 no
    N2 C4 O1 . . 111.5(2) no
    N2 C4 C3 . . 123.4(3) no
    O1 C4 C3 . . 125.2(3) no
    N3 C5 C6 . . 122.9(3) no
    N3 C5 H5 . . 118.6 no
    C6 C5 H5 . . 118.6 no
    C10 C6 C7 . . 104.3(2) no
    C10 C6 C5 . . 123.6(3) no
    C7 C6 C5 . . 132.1(3) no
    N5 C7 C6 . . 111.3(2) yes
    N5 C7 C8 . . 120.0(3) no
    C6 C7 C8 . . 128.6(3) no
    C7 C8 H8A . . 109.5 no
    C7 C8 H8B . . 109.5 no
    H8A C8 H8B . . 109.5 no
    C7 C8 H8C . . 109.5 no
    H8A C8 H8C . . 109.5 no
    H8B C8 H8C . . 109.5 no
    N4 C9 H9A . . 109.5 no
    N4 C9 H9B . . 109.5 no
    H9A C9 H9B . . 109.5 no
    N4 C9 H9C . . 109.5 no
    H9A C9 H9C . . 109.5 no
    H9B C9 H9C . . 109.5 no
    N4 C10 O2 . . 121.2(2) no
    N4 C10 C6 . . 107.9(2) yes
    O2 C10 C6 . . 130.7(2) no
    C12 C11 C18 . . 122.3(2) no
    C12 C11 O2 . . 115.3(2) no
    C18 C11 O2 . . 122.4(2) no
    C11 C12 C13 . . 119.4(3) no
    C11 C12 H12 . . 120.3 no
    C13 C12 H12 . . 120.3 no
    C12 C13 C15 . . 118.5(3) no
    C12 C13 C14 . . 120.8(3) no
    C15 C13 C14 . . 120.8(3) no
    C13 C14 H14A . . 109.5 no
    C13 C14 H14B . . 109.5 no
    H14A C14 H14B . . 109.5 no
    C13 C14 H14C . . 109.5 no
    H14A C14 H14C . . 109.5 no
    H14B C14 H14C . . 109.5 no
    C16 C15 C13 . . 122.3(3) no
    C16 C15 H15 . . 118.9 no
    C13 C15 H15 . . 118.9 no
    C15 C16 C18 . . 118.7(3) no
    C15 C16 C17 . . 121.0(3) no
    C18 C16 C17 . . 120.3(3) no
    C16 C17 H17A . . 109.5 no
    C16 C17 H17B . . 109.5 no
    H17A C17 H17B . . 109.5 no
    C16 C17 H17C . . 109.5 no
    H17A C17 H17C . . 109.5 no
    H17B C17 H17C . . 109.5 no
    C11 C18 C16 . . 118.9(3) no
    C11 C18 H18 . . 120.5 no
    C16 C18 H18 . . 120.5 no
    N6 C19 N7 . . 130.3(3) no
    N6 C19 Cl2 . . 115.1(2) no
    N7 C19 Cl2 . . 114.6(2) no
    N6 C20 C21 . . 124.4(3) no
    N6 C20 H20 . . 117.8 no
    C21 C20 H20 . . 117.8 no
    C20 C21 C22 . . 115.4(3) no
    C20 C21 H21 . . 122.3 no
    C22 C21 H21 . . 122.3 no
    N7 C22 O3 . . 111.5(2) no
    N7 C22 C21 . . 123.1(3) no
    O3 C22 C21 . . 125.4(3) no
    N8 C23 C24 . . 122.5(3) no
    N8 C23 H23 . . 118.7 no
    C24 C23 H23 . . 118.7 no
    C28 C24 C25 . . 103.9(2) no
    C28 C24 C23 . . 123.7(3) no
    C25 C24 C23 . . 132.4(2) no
    N10 C25 C24 . . 111.6(2) no
    N10 C25 C26 . . 119.6(3) no
    C24 C25 C26 . . 128.8(3) no
    C25 C26 H26A . . 109.5 no
    C25 C26 H26B . . 109.5 no
    H26A C26 H26B . . 109.5 no
    C25 C26 H26C . . 109.5 no
    H26A C26 H26C . . 109.5 no
    H26B C26 H26C . . 109.5 no
    N9 C27 H27A . . 109.5 no
    N9 C27 H27B . . 109.5 no
    H27A C27 H27B . . 109.5 no
    N9 C27 H27C . . 109.5 no
    H27A C27 H27C . . 109.5 no
    H27B C27 H27C . . 109.5 no
    N9 C28 O4 . . 120.7(2) no
    N9 C28 C24 . . 108.3(3) no
    O4 C28 C24 . . 130.9(3) no
    C30 C29 C36 . . 122.3(2) no
    C30 C29 O4 . . 115.0(2) no
    C36 C29 O4 . . 122.6(2) no
    C29 C30 C31 . . 119.6(3) no
    C29 C30 H30 . . 120.2 no
    C31 C30 H30 . . 120.2 no
    C30 C31 C33 . . 118.2(3) no
    C30 C31 C32 . . 121.0(3) no
    C33 C31 C32 . . 120.8(3) no
    C31 C32 H32A . . 109.5 no
    C31 C32 H32B . . 109.5 no
    H32A C32 H32B . . 109.5 no
    C31 C32 H32C . . 109.5 no
    H32A C32 H32C . . 109.5 no
    H32B C32 H32C . . 109.5 no
    C34 C33 C31 . . 122.5(3) no
    C34 C33 H33 . . 118.8 no
    C31 C33 H33 . . 118.8 no
    C33 C34 C36 . . 118.2(3) no
    C33 C34 C35 . . 121.1(2) no
    C36 C34 C35 . . 120.7(3) no
    C34 C35 H35A . . 109.5 no
    C34 C35 H35B . . 109.5 no
    H35A C35 H35B . . 109.5 no
    C34 C35 H35C . . 109.5 no
    H35A C35 H35C . . 109.5 no
    H35B C35 H35C . . 109.5 no
    C29 C36 C34 . . 119.3(3) no
    C29 C36 H36 . . 120.4 no
    C34 C36 H36 . . 120.4 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
    C4 O1 N3 C5 . . . . 175.6(2) yes
    C10 N4 N5 C7 . . . . 0.0(3) yes
    C9 N4 N5 C7 . . . . -179.0(3) no
    C22 O3 N8 C23 . . . . 179.5(2) no
    C28 N9 N10 C25 . . . . -0.4(3) no
    C27 N9 N10 C25 . . . . 179.5(3) no
    C2 N1 C1 N2 . . . . -1.0(4) no
    C2 N1 C1 Cl1 . . . . 178.1(2) no
    C4 N2 C1 N1 . . . . 0.3(4) no
    C4 N2 C1 Cl1 . . . . -178.8(2) no
    C1 N1 C2 C3 . . . . 0.2(4) no
    N1 C2 C3 C4 . . . . 1.0(4) no
    C1 N2 C4 O1 . . . . -178.9(2) no
    C1 N2 C4 C3 . . . . 1.3(4) no
    N3 O1 C4 N2 . . . . -173.0(2) no
    N3 O1 C4 C3 . . . . 6.9(4) yes
    C2 C3 C4 N2 . . . . -1.9(4) no
    C2 C3 C4 O1 . . . . 178.3(2) no
    O1 N3 C5 C6 . . . . -178.2(2) no
    N3 C5 C6 C10 . . . . 173.8(3) yes
    N3 C5 C6 C7 . . . . -6.7(5) yes
    N4 N5 C7 C6 . . . . -0.1(3) no
    N4 N5 C7 C8 . . . . -179.6(3) no
    C10 C6 C7 N5 . . . . 0.1(3) yes
    C5 C6 C7 N5 . . . . -179.5(3) no
    C10 C6 C7 C8 . . . . 179.6(3) no
    C5 C6 C7 C8 . . . . 0.0(5) no
    N5 N4 C10 O2 . . . . 174.5(2) no
    C9 N4 C10 O2 . . . . -6.5(4) no
    N5 N4 C10 C6 . . . . 0.1(3) no
    C9 N4 C10 C6 . . . . 179.1(3) no
    C11 O2 C10 N4 . . . . 105.7(3) no
    C11 O2 C10 C6 . . . . -81.3(3) no
    C7 C6 C10 N4 . . . . -0.1(3) no
    C5 C6 C10 N4 . . . . 179.5(2) no
    C7 C6 C10 O2 . . . . -173.8(3) no
    C5 C6 C10 O2 . . . . 5.8(4) no
    C10 O2 C11 C12 . . . . 163.6(2) no
    C10 O2 C11 C18 . . . . -18.2(3) no
    C18 C11 C12 C13 . . . . -0.2(4) no
    O2 C11 C12 C13 . . . . 178.0(2) no
    C11 C12 C13 C15 . . . . 0.9(4) no
    C11 C12 C13 C14 . . . . -179.7(3) no
    C12 C13 C15 C16 . . . . -0.9(4) no
    C14 C13 C15 C16 . . . . 179.7(3) no
    C13 C15 C16 C18 . . . . 0.2(4) no
    C13 C15 C16 C17 . . . . -179.7(3) no
    C12 C11 C18 C16 . . . . -0.5(4) no
    O2 C11 C18 C16 . . . . -178.6(2) no
    C15 C16 C18 C11 . . . . 0.5(4) no
    C17 C16 C18 C11 . . . . -179.6(3) no
    C20 N6 C19 N7 . . . . -1.4(5) no
    C20 N6 C19 Cl2 . . . . 179.2(2) no
    C22 N7 C19 N6 . . . . 0.4(5) no
    C22 N7 C19 Cl2 . . . . 179.9(2) no
    C19 N6 C20 C21 . . . . 1.7(5) no
    N6 C20 C21 C22 . . . . -1.2(5) no
    C19 N7 C22 O3 . . . . 179.8(2) no
    C19 N7 C22 C21 . . . . 0.3(4) no
    N8 O3 C22 N7 . . . . 171.9(2) no
    N8 O3 C22 C21 . . . . -8.6(4) no
    C20 C21 C22 N7 . . . . 0.1(4) no
    C20 C21 C22 O3 . . . . -179.3(3) no
    O3 N8 C23 C24 . . . . 178.3(2) no
    N8 C23 C24 C28 . . . . -178.0(3) no
    N8 C23 C24 C25 . . . . 2.7(5) no
    N9 N10 C25 C24 . . . . 0.6(3) no
    N9 N10 C25 C26 . . . . 179.1(2) no
    C28 C24 C25 N10 . . . . -0.6(3) no
    C23 C24 C25 N10 . . . . 178.8(3) no
    C28 C24 C25 C26 . . . . -178.9(3) no
    C23 C24 C25 C26 . . . . 0.5(5) no
    N10 N9 C28 O4 . . . . -176.1(2) no
    C27 N9 C28 O4 . . . . 4.0(5) no
    N10 N9 C28 C24 . . . . 0.0(3) no
    C27 N9 C28 C24 . . . . -179.8(3) no
    C29 O4 C28 N9 . . . . -106.4(3) no
    C29 O4 C28 C24 . . . . 78.4(4) no
    C25 C24 C28 N9 . . . . 0.3(3) no
    C23 C24 C28 N9 . . . . -179.1(2) no
    C25 C24 C28 O4 . . . . 175.9(3) no
    C23 C24 C28 O4 . . . . -3.5(4) no
    C28 O4 C29 C30 . . . . -163.3(2) no
    C28 O4 C29 C36 . . . . 18.6(4) no
    C36 C29 C30 C31 . . . . -0.8(4) no
    O4 C29 C30 C31 . . . . -178.9(2) no
    C29 C30 C31 C33 . . . . -0.3(4) no
    C29 C30 C31 C32 . . . . 179.0(3) no
    C30 C31 C33 C34 . . . . 0.7(4) no
    C32 C31 C33 C34 . . . . -178.7(3) no
    C31 C33 C34 C36 . . . . 0.1(4) no
    C31 C33 C34 C35 . . . . 179.9(3) no
    C30 C29 C36 C34 . . . . 1.5(4) no
    O4 C29 C36 C34 . . . . 179.5(2) no
    C33 C34 C36 C29 . . . . -1.1(4) no
    C35 C34 C36 C29 . . . . 179.0(3) no
