##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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     2012-04-08
_journal_date_accepted     2012-04-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      5
_journal_page_first     o1456
_journal_page_last     o1456
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812016170
_journal_coeditor_code     LH5453
_publ_contact_author_name     'Prof. Zhou, Cheng-He'
_publ_contact_author_address
;
Laboratory of Bioorganic & Medicinal Chemistry
School of Chemistry and Chemical Engineering
Southwest University
Chongqing 400715,
People's Republic of China
;
_publ_contact_author_email     'zhouch@swu.edu.cn'
_publ_contact_author_fax     '0086-023-68254967'
_publ_contact_author_phone     '0086-023-68254967'
_publ_section_title
;\
(Z)-1,3-Bis(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-\
1-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    ' Dai, Ling-Ling' .
;
Laboratory of Bioorganic & Medicinal Chemistry
School of Chemistry and Chemical Engineering
Southwest University
Chongqing 400715,
People's Republic of China
;
    'Yin, Ben-Tao' .
;
Laboratory of Bioorganic & Medicinal Chemistry
School of Chemistry and Chemical Engineering
Southwest University
Chongqing 400715,
People's Republic of China
;
    'Lv, Jing-Song' .
;
Laboratory of Bioorganic & Medicinal Chemistry
School of Chemistry and Chemical Engineering
Southwest University
Chongqing 400715,
People's Republic of China
;
    'Cui, Sheng-Feng' .
;
Laboratory of Bioorganic & Medicinal Chemistry
School of Chemistry and Chemical Engineering
Southwest University
Chongqing 400715,
People's Republic of China
;
    'Zhou, Cheng-He' .
;
Laboratory of Bioorganic & Medicinal Chemistry
School of Chemistry and Chemical Engineering
Southwest University
Chongqing 400715,
People's Republic of China
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(Z)-1,3-Bis(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-
1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H11 Cl2 N3 O'
_chemical_formula_sum     'C17 H11 Cl2 N3 O'
_chemical_formula_iupac     'C17 H11 Cl2 N3 O'
_chemical_formula_weight     344.19
_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     5.588(3)
_cell_length_b     11.850(7)
_cell_length_c     12.653(8)
_cell_angle_alpha     74.787(10)
_cell_angle_beta     88.884(9)
_cell_angle_gamma     86.461(9)
_cell_volume     807.1(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2086
_cell_measurement_theta_min     3.34
_cell_measurement_theta_max     27.18
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.416
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     352
_exptl_absorpt_coefficient_mu     0.409
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9154
_exptl_absorpt_correction_T_max     0.9412
_exptl_special_details     ?
_diffrn_ambient_temperature     296(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 APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4414
_diffrn_reflns_av_R_equivalents     0.0132
_diffrn_reflns_av_sigmaI/netI     0.0232
_diffrn_reflns_theta_min     3.35
_diffrn_reflns_theta_max     25.99
_diffrn_reflns_theta_full     25.99
_diffrn_measured_fraction_theta_max     0.980
_diffrn_measured_fraction_theta_full     0.980
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     15
_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     3104
_reflns_number_gt     2458
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0479
_refine_ls_R_factor_gt     0.0371
_refine_ls_wR_factor_gt     0.0971
_refine_ls_wR_factor_ref     0.1050
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.022
_refine_ls_number_reflns     3104
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0515P)²+0.1439P] 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     0.211
_refine_diff_density_min     -0.263
_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     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 1.58438(14) 0.60011(6) -0.17465(5) 0.1010(3) Uani d . 1 1 . .
    Cl Cl2 0.14916(9) 0.80981(5) 0.64259(4) 0.07445(19) Uani d . 1 1 . .
    C C1 1.4458(4) 0.6784(2) -0.08893(15) 0.0703(6) Uani d . 1 1 . .
    C C2 1.5551(4) 0.7730(2) -0.07247(16) 0.0719(6) Uani d . 1 1 . .
    H H2A 1.6975 0.7964 -0.1085 0.086 Uiso calc R 1 1 . .
    C C3 1.4505(4) 0.83280(18) -0.00168(16) 0.0654(5) Uani d . 1 1 . .
    H H3A 1.5235 0.8969 0.0100 0.079 Uiso calc R 1 1 . .
    C C4 1.2364(3) 0.79806(16) 0.05257(14) 0.0532(4) Uani d . 1 1 . .
    C C5 1.1286(4) 0.70284(18) 0.03344(15) 0.0637(5) Uani d . 1 1 . .
    H H5A 0.9861 0.6788 0.0691 0.076 Uiso calc R 1 1 . .
    C C6 1.2320(4) 0.6435(2) -0.03847(17) 0.0733(6) Uani d . 1 1 . .
    H H6A 1.1579 0.5808 -0.0525 0.088 Uiso calc R 1 1 . .
    C C7 1.1296(3) 0.87101(16) 0.12331(15) 0.0557(4) Uani d . 1 1 . .
    C C8 0.9716(3) 0.81969(14) 0.21872(14) 0.0487(4) Uani d . 1 1 . .
    C C9 1.1937(3) 0.63087(16) 0.31196(15) 0.0582(5) Uani d . 1 1 . .
    H H9A 1.3439 0.6594 0.3154 0.070 Uiso calc R 1 1 . .
    C C10 0.9086(4) 0.52367(17) 0.32519(19) 0.0736(6) Uani d . 1 1 . .
    H H10A 0.8222 0.4566 0.3425 0.088 Uiso calc R 1 1 . .
    C C11 0.8102(3) 0.88957(15) 0.25517(14) 0.0522(4) Uani d . 1 1 . .
    H H11A 0.7981 0.9669 0.2131 0.063 Uiso calc R 1 1 . .
    C C12 0.6506(3) 0.86366(14) 0.35025(13) 0.0475(4) Uani d . 1 1 . .
    C C13 0.6915(3) 0.77059(16) 0.44322(14) 0.0554(4) Uani d . 1 1 . .
    H H13A 0.8248 0.7190 0.4452 0.067 Uiso calc R 1 1 . .
    C C14 0.5387(3) 0.75364(16) 0.53190(15) 0.0564(4) Uani d . 1 1 . .
    H H14A 0.5684 0.6911 0.5931 0.068 Uiso calc R 1 1 . .
    C C15 0.3405(3) 0.83027(15) 0.52953(14) 0.0524(4) Uani d . 1 1 . .
    C C16 0.2943(3) 0.92271(17) 0.43910(16) 0.0637(5) Uani d . 1 1 . .
    H H16A 0.1595 0.9733 0.4373 0.076 Uiso calc R 1 1 . .
    C C17 0.4495(3) 0.93960(15) 0.35136(15) 0.0586(5) Uani d . 1 1 . .
    H H17A 0.4198 1.0033 0.2911 0.070 Uiso calc R 1 1 . .
    N N1 0.9986(2) 0.69650(11) 0.26747(11) 0.0466(3) Uani d . 1 1 . .
    N N2 0.8100(3) 0.62670(13) 0.27539(14) 0.0621(4) Uani d . 1 1 . .
    N N3 1.1434(3) 0.52092(14) 0.34991(15) 0.0737(5) Uani d . 1 1 . .
    O O1 1.1701(3) 0.97469(12) 0.10500(12) 0.0776(4) Uani d . 1 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 0.1303(6) 0.1091(5) 0.0559(3) 0.0454(4) 0.0020(3) -0.0198(3)
    Cl2 0.0717(3) 0.0773(4) 0.0663(3) 0.0119(3) 0.0173(2) -0.0097(3)
    C1 0.0846(14) 0.0750(14) 0.0403(10) 0.0208(11) 0.0000(9) -0.0016(9)
    C2 0.0633(12) 0.0815(15) 0.0578(12) 0.0082(11) 0.0113(9) 0.0014(10)
    C3 0.0629(11) 0.0632(12) 0.0620(12) -0.0054(9) 0.0100(9) -0.0024(9)
    C4 0.0524(10) 0.0568(10) 0.0446(9) -0.0020(8) 0.0029(7) -0.0033(8)
    C5 0.0644(12) 0.0749(13) 0.0514(11) -0.0129(10) 0.0062(9) -0.0143(9)
    C6 0.0929(16) 0.0733(13) 0.0536(11) -0.0080(11) -0.0012(11) -0.0158(10)
    C7 0.0547(10) 0.0540(11) 0.0542(10) -0.0096(8) 0.0019(8) -0.0052(8)
    C8 0.0478(9) 0.0483(9) 0.0477(9) -0.0061(7) -0.0004(7) -0.0079(7)
    C9 0.0458(9) 0.0616(11) 0.0635(11) 0.0033(8) 0.0018(8) -0.0117(9)
    C10 0.0772(14) 0.0486(11) 0.0915(16) -0.0111(10) 0.0164(12) -0.0116(10)
    C11 0.0581(10) 0.0459(9) 0.0495(9) -0.0011(8) -0.0021(8) -0.0070(7)
    C12 0.0507(9) 0.0439(9) 0.0483(9) -0.0003(7) -0.0032(7) -0.0131(7)
    C13 0.0527(10) 0.0569(10) 0.0523(10) 0.0133(8) -0.0012(8) -0.0102(8)
    C14 0.0606(11) 0.0529(10) 0.0495(10) 0.0077(8) -0.0020(8) -0.0051(8)
    C15 0.0532(10) 0.0534(10) 0.0514(10) 0.0010(8) 0.0013(8) -0.0161(8)
    C16 0.0636(11) 0.0584(11) 0.0634(12) 0.0193(9) 0.0022(9) -0.0113(9)
    C17 0.0719(12) 0.0465(9) 0.0517(10) 0.0112(8) -0.0022(9) -0.0061(8)
    N1 0.0400(7) 0.0463(7) 0.0520(8) -0.0052(6) 0.0049(6) -0.0101(6)
    N2 0.0496(8) 0.0545(9) 0.0815(11) -0.0141(7) 0.0071(8) -0.0146(8)
    N3 0.0744(11) 0.0538(10) 0.0842(12) 0.0101(8) 0.0069(9) -0.0065(8)
    O1 0.0930(10) 0.0584(9) 0.0789(10) -0.0199(7) 0.0262(8) -0.0121(7)
_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
    Cl1 C1 . 1.745(2) ?
    Cl2 C15 . 1.743(2) ?
    C1 C2 . 1.372(3) ?
    C1 C6 . 1.379(3) ?
    C2 C3 . 1.381(3) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.398(3) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.389(3) ?
    C4 C7 . 1.492(3) ?
    C5 C6 . 1.386(3) ?
    C5 H5A . 0.9300 ?
    C6 H6A . 0.9300 ?
    C7 O1 . 1.224(2) ?
    C7 C8 . 1.499(2) ?
    C8 C11 . 1.343(2) ?
    C8 N1 . 1.428(2) ?
    C9 N3 . 1.311(3) ?
    C9 N1 . 1.342(2) ?
    C9 H9A . 0.9300 ?
    C10 N2 . 1.311(3) ?
    C10 N3 . 1.351(3) ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.461(2) ?
    C11 H11A . 0.9300 ?
    C12 C13 . 1.397(2) ?
    C12 C17 . 1.398(2) ?
    C13 C14 . 1.377(2) ?
    C13 H13A . 0.9300 ?
    C14 C15 . 1.384(2) ?
    C14 H14A . 0.9300 ?
    C15 C16 . 1.377(3) ?
    C16 C17 . 1.375(3) ?
    C16 H16A . 0.9300 ?
    C17 H17A . 0.9300 ?
    N1 N2 . 1.366(2) ?
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 C1 C6 . . 121.6(2) ?
    C2 C1 Cl1 . . 118.80(18) ?
    C6 C1 Cl1 . . 119.6(2) ?
    C1 C2 C3 . . 119.1(2) ?
    C1 C2 H2A . . 120.5 ?
    C3 C2 H2A . . 120.5 ?
    C2 C3 C4 . . 120.7(2) ?
    C2 C3 H3A . . 119.6 ?
    C4 C3 H3A . . 119.6 ?
    C5 C4 C3 . . 118.93(19) ?
    C5 C4 C7 . . 123.74(16) ?
    C3 C4 C7 . . 117.23(18) ?
    C6 C5 C4 . . 120.40(19) ?
    C6 C5 H5A . . 119.8 ?
    C4 C5 H5A . . 119.8 ?
    C1 C6 C5 . . 119.2(2) ?
    C1 C6 H6A . . 120.4 ?
    C5 C6 H6A . . 120.4 ?
    O1 C7 C4 . . 120.59(16) ?
    O1 C7 C8 . . 118.20(17) ?
    C4 C7 C8 . . 121.21(16) ?
    C11 C8 N1 . . 122.27(15) ?
    C11 C8 C7 . . 119.71(16) ?
    N1 C8 C7 . . 118.02(14) ?
    N3 C9 N1 . . 110.62(17) ?
    N3 C9 H9A . . 124.7 ?
    N1 C9 H9A . . 124.7 ?
    N2 C10 N3 . . 115.89(18) ?
    N2 C10 H10A . . 122.1 ?
    N3 C10 H10A . . 122.1 ?
    C8 C11 C12 . . 130.38(16) ?
    C8 C11 H11A . . 114.8 ?
    C12 C11 H11A . . 114.8 ?
    C13 C12 C17 . . 117.31(16) ?
    C13 C12 C11 . . 124.22(15) ?
    C17 C12 C11 . . 118.39(15) ?
    C14 C13 C12 . . 121.34(16) ?
    C14 C13 H13A . . 119.3 ?
    C12 C13 H13A . . 119.3 ?
    C13 C14 C15 . . 119.61(16) ?
    C13 C14 H14A . . 120.2 ?
    C15 C14 H14A . . 120.2 ?
    C16 C15 C14 . . 120.58(17) ?
    C16 C15 Cl2 . . 119.85(14) ?
    C14 C15 Cl2 . . 119.56(14) ?
    C17 C16 C15 . . 119.36(17) ?
    C17 C16 H16A . . 120.3 ?
    C15 C16 H16A . . 120.3 ?
    C16 C17 C12 . . 121.78(17) ?
    C16 C17 H17A . . 119.1 ?
    C12 C17 H17A . . 119.1 ?
    C9 N1 N2 . . 109.33(15) ?
    C9 N1 C8 . . 129.36(14) ?
    N2 N1 C8 . . 121.31(13) ?
    C10 N2 N1 . . 101.71(16) ?
    C9 N3 C10 . . 102.45(16) ?
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
    C6 C1 C2 C3 . . . . 1.4(3) ?
    Cl1 C1 C2 C3 . . . . -177.75(14) ?
    C1 C2 C3 C4 . . . . 0.0(3) ?
    C2 C3 C4 C5 . . . . -0.6(3) ?
    C2 C3 C4 C7 . . . . -177.11(17) ?
    C3 C4 C5 C6 . . . . -0.1(3) ?
    C7 C4 C5 C6 . . . . 176.17(18) ?
    C2 C1 C6 C5 . . . . -2.1(3) ?
    Cl1 C1 C6 C5 . . . . 177.06(15) ?
    C4 C5 C6 C1 . . . . 1.4(3) ?
    C5 C4 C7 O1 . . . . -150.2(2) ?
    C3 C4 C7 O1 . . . . 26.1(3) ?
    C5 C4 C7 C8 . . . . 30.1(3) ?
    C3 C4 C7 C8 . . . . -153.57(17) ?
    O1 C7 C8 C11 . . . . 25.1(3) ?
    C4 C7 C8 C11 . . . . -155.23(17) ?
    O1 C7 C8 N1 . . . . -155.21(17) ?
    C4 C7 C8 N1 . . . . 24.5(2) ?
    N1 C8 C11 C12 . . . . 5.7(3) ?
    C7 C8 C11 C12 . . . . -174.66(17) ?
    C8 C11 C12 C13 . . . . 23.4(3) ?
    C8 C11 C12 C17 . . . . -159.82(19) ?
    C17 C12 C13 C14 . . . . 0.6(3) ?
    C11 C12 C13 C14 . . . . 177.44(17) ?
    C12 C13 C14 C15 . . . . -0.2(3) ?
    C13 C14 C15 C16 . . . . 0.4(3) ?
    C13 C14 C15 Cl2 . . . . -179.19(14) ?
    C14 C15 C16 C17 . . . . -1.1(3) ?
    Cl2 C15 C16 C17 . . . . 178.52(15) ?
    C15 C16 C17 C12 . . . . 1.6(3) ?
    C13 C12 C17 C16 . . . . -1.3(3) ?
    C11 C12 C17 C16 . . . . -178.32(18) ?
    N3 C9 N1 N2 . . . . -0.5(2) ?
    N3 C9 N1 C8 . . . . 178.82(17) ?
    C11 C8 N1 C9 . . . . -122.4(2) ?
    C7 C8 N1 C9 . . . . 58.0(2) ?
    C11 C8 N1 N2 . . . . 56.9(2) ?
    C7 C8 N1 N2 . . . . -122.75(17) ?
    N3 C10 N2 N1 . . . . 0.0(2) ?
    C9 N1 N2 C10 . . . . 0.3(2) ?
    C8 N1 N2 C10 . . . . -179.08(16) ?
    N1 C9 N3 C10 . . . . 0.5(2) ?
    N2 C10 N3 C9 . . . . -0.3(3) ?
