##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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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data_041007d
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2004-11-08
_journal_date_accepted     2004-11-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue     12
_journal_page_first     o2404
_journal_page_last     o2405
_journal_paper_category     EO
_publ_contact_author_name     ' Liang-Zhong Xu'
_publ_contact_author_address
;
College of Chemistry and Molecular Engineering
Qingdao University of Science and Technology
Qingdao 266042
People's Republic of China
;
_publ_contact_author_email     youquan_zhu@mail.nankai.edu.cn
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
1-(4-Chlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Liang-Zhong Xu' .
;
College of Chemistry and Molecular Engineering
Qingdao University of Science and Technology
Qingdao 266042
People's Republic of China
;
    'Hai-Bin Song' .
;
State Key Laboratory and Institute of Elemento-Organic Chemistry,
Nankai University, Tianjin
300071, People's Republic of China
;
    'Jin-Hong Liu' .
;
Luoyang Caijing Xuexiao
Luoyang 471002, Henan
People's Republic of China
;
    'Kai Li' .
;
College of Chemistry and Molecular Engineering
Qingdao University of Science and Technology
Qingdao 266042
People's Republic of China
;
    'Guo-Dong Shi' .
;
College of Chemistry and Molecular Engineering
Qingdao University of Science and Technology
Qingdao 266042
People's Republic of China
;
data_I
_chemical_name_systematic
;
1-(4-Chlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H10 Cl N3 O'
_chemical_formula_sum     'C11 H10 Cl N3 O'
_chemical_formula_iupac     'C11 H10 Cl N3 O'
_chemical_formula_weight     235.67
_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     10.1244(19)
_cell_length_b     10.571(2)
_cell_length_c     11.508(2)
_cell_angle_alpha     95.838(3)
_cell_angle_beta     107.625(3)
_cell_angle_gamma     104.906(3)
_cell_volume     1112.6(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2229
_cell_measurement_theta_min     2.49
_cell_measurement_theta_max     25.66
_cell_measurement_temperature     293(2)
_exptl_crystal_description     ' prism '
_exptl_crystal_colour     ' colorless '
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.407
_exptl_crystal_density_meas     NONE
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     488
_exptl_absorpt_coefficient_mu     0.324
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.904
_exptl_absorpt_correction_T_max     0.962
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(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 scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5862
_diffrn_reflns_av_R_equivalents     0.0198
_diffrn_reflns_av_sigmaI/netI     0.0380
_diffrn_reflns_theta_min     2.03
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     11
_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     3905
_reflns_number_gt     2846
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0629
_refine_ls_R_factor_gt     0.0395
_refine_ls_wR_factor_gt     0.0991
_refine_ls_wR_factor_ref     0.1148
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     3905
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0508P)²+0.3475P] 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     0.232
_refine_diff_density_min     -0.308
_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, 1998)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_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_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
    _atom_site_type_symbol
    Cl1 0.17021(7) 0.44227(7) 0.32368(6) 0.0607(2) Uani d . 1 . . Cl
    O1 0.8372(2) 0.86284(17) 0.48045(18) 0.0627(5) Uani d . 1 . . O
    N1 1.1200(2) 0.7823(2) 0.58165(18) 0.0473(5) Uani d . 1 . . N
    N2 1.1605(3) 0.6810(2) 0.6299(2) 0.0595(6) Uani d . 1 . . N
    N3 1.1974(3) 0.8509(2) 0.7830(2) 0.0662(7) Uani d . 1 . . N
    C1 0.5512(3) 0.7250(2) 0.4405(2) 0.0496(6) Uani d . 1 . . C
    H1 0.5890 0.8128 0.4842 0.060 Uiso calc R 1 . . H
    C2 0.4081(3) 0.6567(3) 0.4183(2) 0.0523(6) Uani d . 1 . . C
    H2 0.3500 0.6968 0.4480 0.063 Uiso calc R 1 . . H
    C3 0.3521(3) 0.5280(2) 0.3515(2) 0.0439(6) Uani d . 1 . . C
    C4 0.4367(3) 0.4669(2) 0.3089(2) 0.0529(7) Uani d . 1 . . C
    H4 0.3975 0.3798 0.2639 0.064 Uiso calc R 1 . . H
    C5 0.5809(3) 0.5359(2) 0.3333(2) 0.0509(6) Uani d . 1 . . C
    H5 0.6390 0.4943 0.3051 0.061 Uiso calc R 1 . . H
    C6 0.6404(3) 0.6661(2) 0.3993(2) 0.0390(5) Uani d . 1 . . C
    C7 0.7951(3) 0.7457(2) 0.4299(2) 0.0447(6) Uani d . 1 . . C
    C8 0.8985(3) 0.6810(3) 0.3970(2) 0.0489(6) Uani d . 1 . . C
    H8A 0.8686 0.6570 0.3073 0.059 Uiso calc R 1 . . H
    H8B 0.8923 0.5993 0.4296 0.059 Uiso calc R 1 . . H
    C9 1.0550(3) 0.7693(3) 0.4472(2) 0.0571(7) Uani d . 1 . . C
    H9A 1.1113 0.7323 0.4063 0.069 Uiso calc R 1 . . H
    H9B 1.0590 0.8572 0.4280 0.069 Uiso calc R 1 . . H
    C10 1.2058(3) 0.7288(3) 0.7497(3) 0.0647(8) Uani d . 1 . . C
    H10 1.2417 0.6806 0.8084 0.078 Uiso calc R 1 . . H
    C11 1.1424(3) 0.8803(3) 0.6735(3) 0.0594(7) Uani d . 1 . . C
    H11 1.1220 0.9600 0.6622 0.071 Uiso calc R 1 . . H
    Cl2 0.48649(9) 0.02533(7) 0.33472(6) 0.0689(2) Uani d . 1 . . Cl
    O2 0.0723(2) 0.20184(18) -0.15487(15) 0.0548(5) Uani d . 1 . . O
    N4 -0.2478(2) 0.34816(19) -0.08274(17) 0.0429(5) Uani d . 1 . . N
    N5 -0.2092(2) 0.4715(2) -0.0128(2) 0.0530(5) Uani d . 1 . . N
    N6 -0.4434(2) 0.3627(2) -0.0472(2) 0.0588(6) Uani d . 1 . . N
    C12 0.1369(3) 0.1225(2) 0.1507(2) 0.0397(5) Uani d . 1 . . C
    H12 0.0517 0.1290 0.1623 0.048 Uiso calc R 1 . . H
    C13 0.2354(3) 0.0815(2) 0.2398(2) 0.0458(6) Uani d . 1 . . C
    H13 0.2163 0.0593 0.3105 0.055 Uiso calc R 1 . . H
    C14 0.3615(3) 0.0743(2) 0.2216(2) 0.0455(6) Uani d . 1 . . C
    C15 0.3912(3) 0.1039(2) 0.1167(2) 0.0512(6) Uani d . 1 . . C
    H15 0.4770 0.0980 0.1059 0.061 Uiso calc R 1 . . H
    C16 0.2914(3) 0.1424(2) 0.0278(2) 0.0471(6) Uani d . 1 . . C
    H16 0.3093 0.1608 -0.0443 0.056 Uiso calc R 1 . . H
    C17 0.1648(2) 0.1540(2) 0.0445(2) 0.0376(5) Uani d . 1 . . C
    C18 0.0611(3) 0.1994(2) -0.0528(2) 0.0395(5) Uani d . 1 . . C
    C19 -0.0542(3) 0.2433(2) -0.0200(2) 0.0409(5) Uani d . 1 . . C
    H19A -0.0088 0.3109 0.0556 0.049 Uiso calc R 1 . . H
    H19B -0.1190 0.1678 -0.0034 0.049 Uiso calc R 1 . . H
    C20 -0.1423(3) 0.2991(2) -0.1209(2) 0.0460(6) Uani d . 1 . . C
    H20A -0.0775 0.3715 -0.1411 0.055 Uiso calc R 1 . . H
    H20B -0.1931 0.2300 -0.1951 0.055 Uiso calc R 1 . . H
    C21 -0.3861(3) 0.2866(3) -0.1008(3) 0.0554(7) Uani d . 1 . . C
    H21 -0.4363 0.2003 -0.1459 0.066 Uiso calc R 1 . . H
    C22 -0.3303(3) 0.4742(3) 0.0046(2) 0.0531(7) Uani d . 1 . . C
    H22 -0.3377 0.5485 0.0499 0.064 Uiso calc R 1 . . H
_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 C3 . 1.743(2) no
    O1 C7 . 1.219(3) YES
    N1 C11 . 1.324(3) YES
    N1 N2 . 1.354(3) YES
    N1 C9 . 1.462(3) NO
    N2 C10 . 1.313(3) YES
    N3 C11 . 1.319(3) YES
    N3 C10 . 1.339(4) YES
    C1 C2 . 1.374(4) NO
    C1 C6 . 1.384(3) NO
    C1 H1 . 0.9300 NO
    C2 C3 . 1.374(3) NO
    C2 H2 . 0.9300 NO
    C3 C4 . 1.366(3) NO
    C4 C5 . 1.380(4) NO
    C4 H4 . 0.9300 NO
    C5 C6 . 1.385(3) NO
    C5 H5 . 0.9300 NO
    C6 C7 . 1.488(3) YES
    C7 C8 . 1.504(3) NO
    C8 C9 . 1.513(4) YES
    C8 H8A . 0.9700 NO
    C8 H8B . 0.9700 NO
    C9 H9A . 0.9700 NO
    C9 H9B . 0.9700 NO
    C10 H10 . 0.9300 NO
    C11 H11 . 0.9300 NO
    Cl2 C14 . 1.743(2) NO
    O2 C18 . 1.216(3) YES
    N4 C21 . 1.325(3) YES
    N4 N5 . 1.354(3) YES
    N4 C20 . 1.457(3) YES
    N5 C22 . 1.308(3) YES
    N6 C21 . 1.311(3) YES
    N6 C22 . 1.343(3) YES
    C12 C13 . 1.388(3) NO
    C12 C17 . 1.388(3) NO
    C12 H12 . 0.9300 NO
    C13 C14 . 1.374(4) NO
    C13 H13 . 0.9300 NO
    C14 C15 . 1.377(3) NO
    C15 C16 . 1.379(3) NO
    C15 H15 . 0.9300 NO
    C16 C17 . 1.386(3) NO
    C16 H16 . 0.9300 NO
    C17 C18 . 1.498(3) YES
    C18 C19 . 1.494(3) YES
    C19 C20 . 1.509(3) YES
    C19 H19A . 0.9700 NO
    C19 H19B . 0.9700 NO
    C20 H20A . 0.9700 NO
    C20 H20B . 0.9700 NO
    C21 H21 . 0.9300 NO
    C22 H22 . 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
    C11 N1 N2 . . 109.2(2) YES
    C11 N1 C9 . . 130.1(2) YES
    N2 N1 C9 . . 120.6(2) YES
    C10 N2 N1 . . 101.6(2) YES
    C11 N3 C10 . . 101.2(2) YES
    C2 C1 C6 . . 121.4(2) NO
    C2 C1 H1 . . 119.3 NO
    C6 C1 H1 . . 119.3 NO
    C1 C2 C3 . . 119.1(2) NO
    C1 C2 H2 . . 120.5 NO
    C3 C2 H2 . . 120.5 NO
    C4 C3 C2 . . 121.2(2) NO
    C4 C3 Cl1 . . 120.20(19) NO
    C2 C3 Cl1 . . 118.6(2) NO
    C3 C4 C5 . . 119.3(2) NO
    C3 C4 H4 . . 120.3 NO
    C5 C4 H4 . . 120.3 NO
    C4 C5 C6 . . 121.0(2) NO
    C4 C5 H5 . . 119.5 NO
    C6 C5 H5 . . 119.5 NO
    C1 C6 C5 . . 118.2(2) NO
    C1 C6 C7 . . 118.1(2) NO
    C5 C6 C7 . . 123.7(2) NO
    O1 C7 C6 . . 120.0(2) NO
    O1 C7 C8 . . 120.4(2) NO
    C6 C7 C8 . . 119.6(2) NO
    C7 C8 C9 . . 113.3(2) NO
    C7 C8 H8A . . 108.9 NO
    C9 C8 H8A . . 108.9 NO
    C7 C8 H8B . . 108.9 NO
    C9 C8 H8B . . 108.9 NO
    H8A C8 H8B . . 107.7 NO
    N1 C9 C8 . . 112.3(2) NO
    N1 C9 H9A . . 109.2 NO
    C8 C9 H9A . . 109.2 NO
    N1 C9 H9B . . 109.2 NO
    C8 C9 H9B . . 109.2 NO
    H9A C9 H9B . . 107.9 NO
    N2 C10 N3 . . 116.4(2) NO
    N2 C10 H10 . . 121.8 NO
    N3 C10 H10 . . 121.8 NO
    N3 C11 N1 . . 111.6(2) NO
    N3 C11 H11 . . 124.2 NO
    N1 C11 H11 . . 124.2 NO
    C21 N4 N5 . . 108.9(2) YES
    C21 N4 C20 . . 129.7(2) YES
    N5 N4 C20 . . 121.3(2) YES
    C22 N5 N4 . . 102.2(2) YES
    C21 N6 C22 . . 101.8(2) YES
    C13 C12 C17 . . 120.4(2) NO
    C13 C12 H12 . . 119.8 NO
    C17 C12 H12 . . 119.8 NO
    C14 C13 C12 . . 118.8(2) NO
    C14 C13 H13 . . 120.6 NO
    C12 C13 H13 . . 120.6 NO
    C13 C14 C15 . . 121.9(2) NO
    C13 C14 Cl2 . . 118.82(19) NO
    C15 C14 Cl2 . . 119.3(2) NO
    C14 C15 C16 . . 118.8(2) NO
    C14 C15 H15 . . 120.6 NO
    C16 C15 H15 . . 120.6 NO
    C15 C16 C17 . . 120.9(2) NO
    C15 C16 H16 . . 119.5 NO
    C17 C16 H16 . . 119.5 NO
    C16 C17 C12 . . 119.2(2) NO
    C16 C17 C18 . . 119.2(2) NO
    C12 C17 C18 . . 121.7(2) NO
    O2 C18 C19 . . 121.3(2) NO
    O2 C18 C17 . . 120.6(2) NO
    C19 C18 C17 . . 118.08(19) NO
    C18 C19 C20 . . 113.11(18) NO
    C18 C19 H19A . . 109.0 NO
    C20 C19 H19A . . 109.0 NO
    C18 C19 H19B . . 109.0 NO
    C20 C19 H19B . . 109.0 NO
    H19A C19 H19B . . 107.8 NO
    N4 C20 C19 . . 111.57(18) NO
    N4 C20 H20A . . 109.3 NO
    C19 C20 H20A . . 109.3 NO
    N4 C20 H20B . . 109.3 NO
    C19 C20 H20B . . 109.3 NO
    H20A C20 H20B . . 108.0 NO
    N6 C21 N4 . . 111.4(2) NO
    N6 C21 H21 . . 124.3 NO
    N4 C21 H21 . . 124.3 NO
    N5 C22 N6 . . 115.6(2) NO
    N5 C22 H22 . . 122.2 NO
    N6 C22 H22 . . 122.2 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
    C11 N1 N2 C10 . . . . -0.4(3) NO
    C9 N1 N2 C10 . . . . -177.2(2) NO
    C6 C1 C2 C3 . . . . -1.3(4) NO
    C1 C2 C3 C4 . . . . 1.0(4) NO
    C1 C2 C3 Cl1 . . . . -179.90(19) NO
    C2 C3 C4 C5 . . . . 0.0(4) NO
    Cl1 C3 C4 C5 . . . . -179.14(19) NO
    C3 C4 C5 C6 . . . . -0.6(4) NO
    C2 C1 C6 C5 . . . . 0.7(3) NO
    C2 C1 C6 C7 . . . . -178.5(2) NO
    C4 C5 C6 C1 . . . . 0.3(4) NO
    C4 C5 C6 C7 . . . . 179.4(2) NO
    C1 C6 C7 O1 . . . . -6.1(3) NO
    C5 C6 C7 O1 . . . . 174.7(2) NO
    C1 C6 C7 C8 . . . . 174.4(2) NO
    C5 C6 C7 C8 . . . . -4.8(3) NO
    O1 C7 C8 C9 . . . . 7.3(3) NO
    C6 C7 C8 C9 . . . . -173.22(19) NO
    C11 N1 C9 C8 . . . . -100.8(3) NO
    N2 N1 C9 C8 . . . . 75.3(3) NO
    C7 C8 C9 N1 . . . . 73.1(3) NO
    N1 N2 C10 N3 . . . . 0.4(3) NO
    C11 N3 C10 N2 . . . . -0.2(4) NO
    C10 N3 C11 N1 . . . . -0.1(3) NO
    N2 N1 C11 N3 . . . . 0.3(3) NO
    C9 N1 C11 N3 . . . . 176.7(2) NO
    C21 N4 N5 C22 . . . . -0.6(3) NO
    C20 N4 N5 C22 . . . . -177.6(2) NO
    C17 C12 C13 C14 . . . . 0.8(3) NO
    C12 C13 C14 C15 . . . . -1.4(4) NO
    C12 C13 C14 Cl2 . . . . 178.99(17) NO
    C13 C14 C15 C16 . . . . 0.3(4) NO
    Cl2 C14 C15 C16 . . . . 179.94(19) NO
    C14 C15 C16 C17 . . . . 1.3(4) NO
    C15 C16 C17 C12 . . . . -1.9(3) NO
    C15 C16 C17 C18 . . . . 178.5(2) NO
    C13 C12 C17 C16 . . . . 0.8(3) NO
    C13 C12 C17 C18 . . . . -179.6(2) NO
    C16 C17 C18 O2 . . . . 13.8(3) NO
    C12 C17 C18 O2 . . . . -165.8(2) NO
    C16 C17 C18 C19 . . . . -165.2(2) NO
    C12 C17 C18 C19 . . . . 15.2(3) NO
    O2 C18 C19 C20 . . . . -4.6(3) NO
    C17 C18 C19 C20 . . . . 174.4(2) NO
    C21 N4 C20 C19 . . . . -93.5(3) NO
    N5 N4 C20 C19 . . . . 82.8(3) NO
    C18 C19 C20 N4 . . . . -176.58(19) NO
    C22 N6 C21 N4 . . . . -0.1(3) NO
    N5 N4 C21 N6 . . . . 0.4(3) NO
    C20 N4 C21 N6 . . . . 177.1(2) NO
    N4 N5 C22 N6 . . . . 0.6(3) NO
    C21 N6 C22 N5 . . . . -0.3(3) NO
