##############################################################################
###                                                                        ###
###        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/  #
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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-09-20
_journal_date_accepted     2006-09-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     11
_journal_page_first     o4780
_journal_page_last     o4782
_journal_paper_category     EO
_journal_coeditor_code     AT2121
_publ_contact_author_name     'Prof. Dr De-Qing Shi'
_publ_contact_author_address
;
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education
College of Chemistry
Central China Normal University
Wuhan  430079
Hubei
People's Republic of China
;
_publ_contact_author_email     chshidq@yahoo.com.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     '86-27-67867958(office)'
_publ_section_title
;
3-(6-Chloropyridin-3-ylmethyl)-6-propyl-6,7-dihydro-3H-1,2,3-
triazolo[4,5-d]pyrimidin-7-imine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Xiao-Bao Chen' .
; Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education
  College of Chemistry
  Central China Normal University
  Wuhan  430079
  Hubei
  People's Republic of China
;
    'De-Qing Shi' .
; Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education
  College of Chemistry
  Central China Normal University
  Wuhan  430079
  Hubei
  People's Republic of China
;
data_I
_chemical_name_systematic
;
3-(6-Chloropyridin-3-ylmethyl)-6-propyl-6,7-dihydro-3H-1,2,3-
triazolo[4,5-d]pyrimidin-7-imine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H14 Cl N7'
_chemical_formula_sum     'C13 H14 Cl N7'
_chemical_formula_iupac     'C13 H14 Cl N7'
_chemical_formula_weight     303.76
_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     7.1644(9)
_cell_length_b     13.1572(16)
_cell_length_c     15.6765(19)
_cell_angle_alpha     91.008(2)
_cell_angle_beta     99.321(2)
_cell_angle_gamma     96.281(2)
_cell_volume     1448.5(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3445
_cell_measurement_theta_min     2.63
_cell_measurement_theta_max     26.73
_cell_measurement_temperature     298(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.393
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     632
_exptl_absorpt_coefficient_mu     0.269
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     0.9094
_exptl_absorpt_correction_T_max     0.9841
_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     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8283
_diffrn_reflns_av_R_equivalents     0.0222
_diffrn_reflns_av_sigmaI/netI     0.0381
_diffrn_reflns_theta_min     1.56
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.982
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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     5029
_reflns_number_gt     3970
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0774
_refine_ls_R_factor_gt     0.0627
_refine_ls_wR_factor_gt     0.1742
_refine_ls_wR_factor_ref     0.1851
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_restrained_S_all     1.048
_refine_ls_number_reflns     5029
_refine_ls_number_parameters     384
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0964P)²+0.678P] 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     0.495
_refine_diff_density_min     -0.432
_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'
    '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, 2000)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_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
    C C1 0.2421(4) 0.13915(19) 0.22453(18) 0.0483(7) Uani d . 1 . .
    C C2 0.2734(6) 0.1178(3) 0.1419(2) 0.0697(9) Uani d . 1 . .
    H H2 0.3929 0.1039 0.1322 0.084 Uiso calc R 1 . .
    C C3 0.1252(7) 0.1174(3) 0.0742(2) 0.0806(11) Uani d . 1 . .
    H H3 0.1424 0.1038 0.0178 0.097 Uiso calc R 1 . .
    C C4 -0.0473(6) 0.1373(2) 0.0916(2) 0.0670(9) Uani d . 1 . .
    C C5 0.0623(5) 0.1589(2) 0.23316(19) 0.0600(8) Uani d . 1 . .
    H H5 0.0404 0.1741 0.2886 0.072 Uiso calc R 1 . .
    C C6 0.3969(4) 0.1421(2) 0.30182(18) 0.0523(7) Uani d . 1 . .
    H H6A 0.5129 0.1253 0.2832 0.063 Uiso calc R 1 . .
    H H6B 0.4213 0.2109 0.3273 0.063 Uiso calc R 1 . .
    C C7 0.2961(3) 0.08996(18) 0.44410(16) 0.0391(6) Uani d . 1 . .
    C C8 0.2660(3) -0.00361(17) 0.47875(16) 0.0366(5) Uani d . 1 . .
    C C9 0.2110(3) -0.01297(18) 0.56287(16) 0.0389(6) Uani d . 1 . .
    C C10 0.2265(4) 0.17310(19) 0.55525(19) 0.0490(7) Uani d . 1 . .
    H H10 0.2098 0.2333 0.5837 0.059 Uiso calc R 1 . .
    C C11 0.1423(4) 0.0936(2) 0.68451(19) 0.0558(7) Uani d . 1 . .
    H H11A 0.0629 0.1487 0.6853 0.067 Uiso calc R 1 . .
    H H11B 0.0662 0.0307 0.6946 0.067 Uiso calc R 1 . .
    C C12 0.3011(7) 0.1122(5) 0.7553(3) 0.122(2) Uani d . 1 . .
    H H12A 0.3848 0.1710 0.7425 0.146 Uiso calc R 1 . .
    H H12B 0.3728 0.0535 0.7588 0.146 Uiso calc R 1 . .
    C C13 0.2436(7) 0.1312(4) 0.8419(3) 0.1106(16) Uani d . 1 . .
    H H13A 0.1616 0.1846 0.8376 0.166 Uiso calc R 1 . .
    H H13B 0.3552 0.1516 0.8840 0.166 Uiso calc R 1 . .
    H H13C 0.1774 0.0697 0.8594 0.166 Uiso calc R 1 . .
    C C14 0.3600(4) 0.62323(19) 0.80702(18) 0.0499(7) Uani d . 1 . .
    C C15 0.3335(6) 0.6294(3) 0.8919(2) 0.0698(9) Uani d . 1 . .
    H H15 0.2131 0.6348 0.9054 0.084 Uiso calc R 1 . .
    C C16 0.4883(7) 0.6274(3) 0.9567(2) 0.0821(11) Uani d . 1 . .
    H H16 0.4752 0.6314 1.0147 0.098 Uiso calc R 1 . .
    C C17 0.6611(6) 0.6194(2) 0.9328(2) 0.0691(9) Uani d . 1 . .
    C C18 0.5418(5) 0.6147(2) 0.79213(19) 0.0545(7) Uani d . 1 . .
    H H18 0.5609 0.6106 0.7349 0.065 Uiso calc R 1 . .
    C C19 0.1959(4) 0.6280(2) 0.73455(18) 0.0531(7) Uani d . 1 . .
    H H19A 0.0776 0.6089 0.7558 0.064 Uiso calc R 1 . .
    H H19B 0.1953 0.6978 0.7157 0.064 Uiso calc R 1 . .
    C C20 0.2321(4) 0.58421(18) 0.58003(17) 0.0405(6) Uani d . 1 . .
    C C21 0.2320(3) 0.49217(18) 0.53819(16) 0.0391(6) Uani d . 1 . .
    C C22 0.2627(4) 0.48746(18) 0.44971(17) 0.0413(6) Uani d . 1 . .
    C C23 0.2789(4) 0.6733(2) 0.4675(2) 0.0533(7) Uani d . 1 . .
    H H23 0.2960 0.7353 0.4405 0.064 Uiso calc R 1 . .
    C C24 0.3081(6) 0.5959(3) 0.3272(2) 0.0674(9) Uani d . 1 . .
    H H24A 0.4427 0.5955 0.3253 0.081 Uiso calc R 1 . .
    H H24B 0.2422 0.5347 0.2958 0.081 Uiso calc R 1 . .
    C C25 0.2455(8) 0.6829(3) 0.2813(3) 0.0998(14) Uani d . 1 . .
    H H25A 0.3181 0.7450 0.3083 0.120 Uiso calc R 1 . .
    H H25B 0.1123 0.6868 0.2843 0.120 Uiso calc R 1 . .
    C C26 0.2719(9) 0.6744(4) 0.1863(2) 0.1165(18) Uani d . 1 . .
    H H26A 0.4039 0.6709 0.1834 0.175 Uiso calc R 1 . .
    H H26B 0.2307 0.7333 0.1567 0.175 Uiso calc R 1 . .
    H H26C 0.1977 0.6137 0.1593 0.175 Uiso calc R 1 . .
    Cl Cl1 -0.2405(2) 0.13351(9) 0.00703(7) 0.1122(5) Uani d . 1 . .
    Cl Cl2 0.85935(19) 0.61704(10) 1.01450(7) 0.1096(4) Uani d . 1 . .
    N N1 -0.0844(4) 0.1579(2) 0.16830(18) 0.0722(8) Uani d . 1 . .
    N N2 0.3474(3) 0.07072(15) 0.36722(14) 0.0425(5) Uani d . 1 . .
    N N3 0.3477(3) -0.03175(15) 0.35419(14) 0.0449(5) Uani d . 1 . .
    N N4 0.2986(3) -0.07707(15) 0.42239(13) 0.0410(5) Uani d . 1 . .
    N N5 0.1944(3) 0.08556(15) 0.59784(14) 0.0441(5) Uani d . 1 . .
    N N6 0.2776(3) 0.18324(15) 0.47982(15) 0.0481(6) Uani d . 1 . .
    N N7 0.1767(3) -0.09161(16) 0.60640(14) 0.0466(5) Uani d D 1 . .
    H H7 0.1958 -0.1457 0.5790 0.056 Uiso d RD 1 . .
    N N8 0.6928(4) 0.6118(2) 0.85407(18) 0.0639(7) Uani d . 1 . .
    N N9 0.2053(3) 0.56058(15) 0.66061(14) 0.0456(5) Uani d . 1 . .
    N N10 0.1872(4) 0.45739(16) 0.66851(15) 0.0526(6) Uani d . 1 . .
    N N11 0.2049(3) 0.41570(15) 0.59325(15) 0.0478(6) Uani d . 1 . .
    N N12 0.2818(3) 0.58796(16) 0.41792(14) 0.0468(5) Uani d . 1 . .
    N N13 0.2552(3) 0.67950(16) 0.54768(15) 0.0510(6) Uani d . 1 . .
    N N14 0.2744(4) 0.41123(17) 0.40056(16) 0.0534(6) Uani d D 1 . .
    H H14 0.265(5) 0.3553(15) 0.4277(18) 0.064 Uiso d D 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
    C1 C5 . 1.369(4) ?
    C1 C2 . 1.379(4) ?
    C1 C6 . 1.501(4) ?
    C2 C3 . 1.374(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.359(5) ?
    C3 H3 . 0.9300 ?
    C4 N1 . 1.302(4) ?
    C4 Cl1 . 1.751(4) ?
    C5 N1 . 1.338(4) ?
    C5 H5 . 0.9300 ?
    C6 N2 . 1.462(3) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 N2 . 1.344(3) yes
    C7 C8 . 1.364(3) ?
    C7 N6 . 1.368(3) yes
    C8 N4 . 1.362(3) yes
    C8 C9 . 1.440(3) yes
    C9 N7 . 1.273(3) yes
    C9 N5 . 1.423(3) ?
    C10 N6 . 1.298(3) ?
    C10 N5 . 1.358(3) yes
    C10 H10 . 0.9300 ?
    C11 C12 . 1.451(5) ?
    C11 N5 . 1.471(3) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.506(5) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C14 C18 . 1.376(4) ?
    C14 C15 . 1.377(4) ?
    C14 C19 . 1.505(4) ?
    C15 C16 . 1.381(5) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.365(6) ?
    C16 H16 . 0.9300 ?
    C17 N8 . 1.294(4) ?
    C17 Cl2 . 1.755(4) ?
    C18 N8 . 1.336(4) ?
    C18 H18 . 0.9300 ?
    C19 N9 . 1.462(3) ?
    C19 H19A . 0.9700 ?
    C19 H19B . 0.9700 ?
    C20 N9 . 1.345(3) ?
    C20 N13 . 1.364(3) ?
    C20 C21 . 1.367(3) ?
    C21 N11 . 1.355(3) ?
    C21 C22 . 1.440(3) ?
    C22 N14 . 1.272(3) ?
    C22 N12 . 1.422(3) ?
    C23 N13 . 1.298(4) ?
    C23 N12 . 1.359(3) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.438(5) ?
    C24 N12 . 1.468(4) ?
    C24 H24A . 0.9700 ?
    C24 H24B . 0.9700 ?
    C25 C26 . 1.535(6) ?
    C25 H25A . 0.9700 ?
    C25 H25B . 0.9700 ?
    C26 H26A . 0.9600 ?
    C26 H26B . 0.9600 ?
    C26 H26C . 0.9600 ?
    N2 N3 . 1.360(3) ?
    N3 N4 . 1.312(3) ?
    N7 H7 . 0.8595 ?
    N9 N10 . 1.359(3) ?
    N10 N11 . 1.323(3) ?
    N14 H14 . 0.858(10) ?
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
    C5 C1 C2 . . 116.8(3) ?
    C5 C1 C6 . . 121.0(3) ?
    C2 C1 C6 . . 122.2(3) ?
    C3 C2 C1 . . 118.9(3) ?
    C3 C2 H2 . . 120.5 ?
    C1 C2 H2 . . 120.5 ?
    C4 C3 C2 . . 118.5(3) ?
    C4 C3 H3 . . 120.8 ?
    C2 C3 H3 . . 120.8 ?
    N1 C4 C3 . . 125.1(3) ?
    N1 C4 Cl1 . . 115.5(3) ?
    C3 C4 Cl1 . . 119.4(3) ?
    N1 C5 C1 . . 125.3(3) ?
    N1 C5 H5 . . 117.4 ?
    C1 C5 H5 . . 117.4 ?
    N2 C6 C1 . . 112.3(2) ?
    N2 C6 H6A . . 109.1 ?
    C1 C6 H6A . . 109.1 ?
    N2 C6 H6B . . 109.1 ?
    C1 C6 H6B . . 109.1 ?
    H6A C6 H6B . . 107.9 ?
    N2 C7 C8 . . 105.1(2) ?
    N2 C7 N6 . . 127.4(2) ?
    C8 C7 N6 . . 127.5(2) ?
    N4 C8 C7 . . 109.1(2) ?
    N4 C8 C9 . . 130.1(2) ?
    C7 C8 C9 . . 120.9(2) ?
    N7 C9 N5 . . 119.3(2) ?
    N7 C9 C8 . . 130.8(2) ?
    N5 C9 C8 . . 109.9(2) ?
    N6 C10 N5 . . 128.1(2) ?
    N6 C10 H10 . . 116.0 ?
    N5 C10 H10 . . 116.0 ?
    C12 C11 N5 . . 115.3(3) ?
    C12 C11 H11A . . 108.4 ?
    N5 C11 H11A . . 108.4 ?
    C12 C11 H11B . . 108.4 ?
    N5 C11 H11B . . 108.4 ?
    H11A C11 H11B . . 107.5 ?
    C11 C12 C13 . . 114.1(4) ?
    C11 C12 H12A . . 108.7 ?
    C13 C12 H12A . . 108.7 ?
    C11 C12 H12B . . 108.7 ?
    C13 C12 H12B . . 108.7 ?
    H12A C12 H12B . . 107.6 ?
    C12 C13 H13A . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C12 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C18 C14 C15 . . 117.2(3) ?
    C18 C14 C19 . . 122.2(3) ?
    C15 C14 C19 . . 120.5(3) ?
    C14 C15 C16 . . 119.0(3) ?
    C14 C15 H15 . . 120.5 ?
    C16 C15 H15 . . 120.5 ?
    C17 C16 C15 . . 117.7(3) ?
    C17 C16 H16 . . 121.2 ?
    C15 C16 H16 . . 121.2 ?
    N8 C17 C16 . . 125.6(3) ?
    N8 C17 Cl2 . . 116.1(3) ?
    C16 C17 Cl2 . . 118.2(3) ?
    N8 C18 C14 . . 124.6(3) ?
    N8 C18 H18 . . 117.7 ?
    C14 C18 H18 . . 117.7 ?
    N9 C19 C14 . . 112.5(2) ?
    N9 C19 H19A . . 109.1 ?
    C14 C19 H19A . . 109.1 ?
    N9 C19 H19B . . 109.1 ?
    C14 C19 H19B . . 109.1 ?
    H19A C19 H19B . . 107.8 ?
    N9 C20 N13 . . 127.2(2) ?
    N9 C20 C21 . . 104.9(2) ?
    N13 C20 C21 . . 127.8(2) ?
    N11 C21 C20 . . 109.3(2) ?
    N11 C21 C22 . . 129.9(2) ?
    C20 C21 C22 . . 120.7(2) ?
    N14 C22 N12 . . 119.6(2) ?
    N14 C22 C21 . . 130.7(2) ?
    N12 C22 C21 . . 109.7(2) ?
    N13 C23 N12 . . 128.3(3) ?
    N13 C23 H23 . . 115.9 ?
    N12 C23 H23 . . 115.9 ?
    C25 C24 N12 . . 117.9(3) ?
    C25 C24 H24A . . 107.8 ?
    N12 C24 H24A . . 107.8 ?
    C25 C24 H24B . . 107.8 ?
    N12 C24 H24B . . 107.8 ?
    H24A C24 H24B . . 107.2 ?
    C24 C25 C26 . . 110.5(4) ?
    C24 C25 H25A . . 109.6 ?
    C26 C25 H25A . . 109.6 ?
    C24 C25 H25B . . 109.6 ?
    C26 C25 H25B . . 109.6 ?
    H25A C25 H25B . . 108.1 ?
    C25 C26 H26A . . 109.5 ?
    C25 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C25 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C4 N1 C5 . . 115.5(3) ?
    C7 N2 N3 . . 110.02(19) ?
    C7 N2 C6 . . 129.4(2) ?
    N3 N2 C6 . . 120.6(2) ?
    N4 N3 N2 . . 107.75(19) ?
    N3 N4 C8 . . 108.07(19) ?
    C10 N5 C9 . . 123.0(2) ?
    C10 N5 C11 . . 118.2(2) ?
    C9 N5 C11 . . 118.8(2) ?
    C10 N6 C7 . . 110.7(2) ?
    C9 N7 H7 . . 110.0 ?
    C17 N8 C18 . . 115.9(3) ?
    C20 N9 N10 . . 110.2(2) ?
    C20 N9 C19 . . 129.6(2) ?
    N10 N9 C19 . . 120.1(2) ?
    N11 N10 N9 . . 107.4(2) ?
    N10 N11 C21 . . 108.1(2) ?
    C23 N12 C22 . . 123.1(2) ?
    C23 N12 C24 . . 120.6(2) ?
    C22 N12 C24 . . 116.3(2) ?
    C23 N13 C20 . . 110.4(2) ?
    C22 N14 H14 . . 111(2) ?
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
    C5 C1 C2 C3 . . . . -0.1(5) ?
    C6 C1 C2 C3 . . . . -179.4(3) ?
    C1 C2 C3 C4 . . . . -0.5(5) ?
    C2 C3 C4 N1 . . . . 0.5(6) ?
    C2 C3 C4 Cl1 . . . . -178.1(3) ?
    C2 C1 C5 N1 . . . . 0.7(5) ?
    C6 C1 C5 N1 . . . . -179.9(3) ?
    C5 C1 C6 N2 . . . . 58.0(3) ?
    C2 C1 C6 N2 . . . . -122.6(3) ?
    N2 C7 C8 N4 . . . . -0.3(3) ?
    N6 C7 C8 N4 . . . . 179.6(2) ?
    N2 C7 C8 C9 . . . . 179.0(2) ?
    N6 C7 C8 C9 . . . . -1.1(4) ?
    N4 C8 C9 N7 . . . . -0.8(4) ?
    C7 C8 C9 N7 . . . . -179.9(3) ?
    N4 C8 C9 N5 . . . . 179.8(2) ?
    C7 C8 C9 N5 . . . . 0.6(3) ?
    N5 C11 C12 C13 . . . . 173.8(4) ?
    C18 C14 C15 C16 . . . . 0.4(5) ?
    C19 C14 C15 C16 . . . . -178.3(3) ?
    C14 C15 C16 C17 . . . . 0.0(5) ?
    C15 C16 C17 N8 . . . . -1.2(6) ?
    C15 C16 C17 Cl2 . . . . 179.9(3) ?
    C15 C14 C18 N8 . . . . 0.1(4) ?
    C19 C14 C18 N8 . . . . 178.9(3) ?
    C18 C14 C19 N9 . . . . 38.1(4) ?
    C15 C14 C19 N9 . . . . -143.2(3) ?
    N9 C20 C21 N11 . . . . 0.2(3) ?
    N13 C20 C21 N11 . . . . 179.9(2) ?
    N9 C20 C21 C22 . . . . -178.3(2) ?
    N13 C20 C21 C22 . . . . 1.4(4) ?
    N11 C21 C22 N14 . . . . -0.8(5) ?
    C20 C21 C22 N14 . . . . 177.3(3) ?
    N11 C21 C22 N12 . . . . 179.4(2) ?
    C20 C21 C22 N12 . . . . -2.5(3) ?
    N12 C24 C25 C26 . . . . -176.2(4) ?
    C3 C4 N1 C5 . . . . 0.1(5) ?
    Cl1 C4 N1 C5 . . . . 178.7(2) ?
    C1 C5 N1 C4 . . . . -0.7(5) ?
    C8 C7 N2 N3 . . . . 0.5(3) ?
    N6 C7 N2 N3 . . . . -179.4(2) ?
    C8 C7 N2 C6 . . . . 179.9(2) ?
    N6 C7 N2 C6 . . . . 0.1(4) ?
    C1 C6 N2 C7 . . . . -106.0(3) ?
    C1 C6 N2 N3 . . . . 73.5(3) ?
    C7 N2 N3 N4 . . . . -0.5(3) ?
    C6 N2 N3 N4 . . . . 180.0(2) ?
    N2 N3 N4 C8 . . . . 0.3(3) ?
    C7 C8 N4 N3 . . . . 0.0(3) ?
    C9 C8 N4 N3 . . . . -179.2(2) ?
    N6 C10 N5 C9 . . . . -0.9(4) ?
    N6 C10 N5 C11 . . . . 178.4(3) ?
    N7 C9 N5 C10 . . . . -179.3(2) ?
    C8 C9 N5 C10 . . . . 0.2(3) ?
    N7 C9 N5 C11 . . . . 1.5(3) ?
    C8 C9 N5 C11 . . . . -179.0(2) ?
    C12 C11 N5 C10 . . . . -85.9(4) ?
    C12 C11 N5 C9 . . . . 93.4(4) ?
    N5 C10 N6 C7 . . . . 0.5(4) ?
    N2 C7 N6 C10 . . . . -179.7(2) ?
    C8 C7 N6 C10 . . . . 0.5(4) ?
    C16 C17 N8 C18 . . . . 1.7(5) ?
    Cl2 C17 N8 C18 . . . . -179.3(2) ?
    C14 C18 N8 C17 . . . . -1.2(4) ?
    N13 C20 N9 N10 . . . . 179.7(2) ?
    C21 C20 N9 N10 . . . . -0.6(3) ?
    N13 C20 N9 C19 . . . . -0.8(4) ?
    C21 C20 N9 C19 . . . . 178.9(3) ?
    C14 C19 N9 C20 . . . . -113.6(3) ?
    C14 C19 N9 N10 . . . . 65.9(3) ?
    C20 N9 N10 N11 . . . . 0.8(3) ?
    C19 N9 N10 N11 . . . . -178.8(2) ?
    N9 N10 N11 C21 . . . . -0.6(3) ?
    C20 C21 N11 N10 . . . . 0.3(3) ?
    C22 C21 N11 N10 . . . . 178.6(3) ?
    N13 C23 N12 C22 . . . . -1.6(5) ?
    N13 C23 N12 C24 . . . . 179.2(3) ?
    N14 C22 N12 C23 . . . . -177.2(3) ?
    C21 C22 N12 C23 . . . . 2.6(3) ?
    N14 C22 N12 C24 . . . . 2.0(4) ?
    C21 C22 N12 C24 . . . . -178.2(2) ?
    C25 C24 N12 C23 . . . . -27.9(5) ?
    C25 C24 N12 C22 . . . . 152.9(4) ?
    N12 C23 N13 C20 . . . . 0.2(4) ?
    N9 C20 N13 C23 . . . . 179.6(3) ?
    C21 C20 N13 C23 . . . . -0.1(4) ?
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
    C23 H23 N4 1_565 0.93 2.49 3.364(3) 156.9
    C18 H18 N14 2_666 0.93 2.62 3.511(4) 161.2
    C10 H10 N11 . 0.93 2.41 3.262(3) 152.8
    C5 H5 N7 2_556 0.93 2.61 3.344(4) 135.8
    N14 H14 N6 . 0.858(10) 2.426(13) 3.268(3) 167(3)
    N7 H7 N13 1_545 0.86 2.44 3.267(3) 161.6
    C11 H11B Cg1 2_556 0.97 2.94 3.4780(10)
                                          116
    C24 H24A Cg2 2_666 0.97 2.96 3.792(4) 145
