##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2008-07-16
_journal_date_accepted     2008-07-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1619
_journal_page_last     o1619
_journal_paper_category     QO
_journal_coeditor_code     DN2368
_publ_contact_author_name     'Professor Jun Wan'
_publ_contact_author_address
;
College of Chemistry and Molecular Engineering
Qingdao University of Science and Technology
266042 Qingdao
Shandong
People's Republic of China
;
_publ_contact_author_email     qustchemistry@126.com
_publ_contact_author_fax     '+86 532 84022750'
_publ_contact_author_phone     '+86 532 84022750'
_publ_section_title
;
2-(1H-Benzotriazol-1-yl)-1-(2-chlorobenzoyl)ethyl 4-methylbenzoate
;
loop_
    _publ_author_name
    _publ_author_address
    'Lin-Bin Jiang'
;
College of Chemistry and Chemical Engineering
Guangxi University
530004 Nanning
Guangxi
People's Republic of China
;
    'Lin Li'
;
College of Chemistry and Chemical Engineering
Guangxi University
530004 Nanning
Guangxi
People's Republic of China
;
    'Yao Liu'
;
College of Chemistry and Molecular Engineering
Qingdao University of Science and Technology
266042 Qingdao
Shandong
People's Republic of China
;
    'Na-Na Tian'
;
College of Chemistry and Molecular Engineering
Qingdao University of Science and Technology
266042 Qingdao
Shandong
People's Republic of China
;
    'Jun Wan'
;
College of Chemistry and Molecular Engineering
Qingdao University of Science and Technology
266042 Qingdao
Shandong
People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2-(1H-Benzotriazol-1-yl)-1-(2-chlorobenzoyl)ethyl 4-methylbenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H18 Cl N3 O3'
_chemical_formula_sum     'C23 H18 Cl N3 O3'
_chemical_formula_iupac     'C23 H18 Cl N3 O3'
_chemical_formula_weight     419.85
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     7.9254(7)
_cell_length_b     26.151(2)
_cell_length_c     10.6002(9)
_cell_angle_alpha     90.00
_cell_angle_beta     107.8950(10)
_cell_angle_gamma     90.00
_cell_volume     2090.7(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2285
_cell_measurement_theta_min     2.55
_cell_measurement_theta_max     21.51
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.17
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.334
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     872
_exptl_absorpt_coefficient_mu     0.212
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.934
_exptl_absorpt_correction_T_max     0.983
_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     'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     11618
_diffrn_reflns_av_R_equivalents     0.0316
_diffrn_reflns_av_sigmaI/netI     0.0398
_diffrn_reflns_theta_min     2.16
_diffrn_reflns_theta_max     26.04
_diffrn_reflns_theta_full     26.04
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -31
_diffrn_reflns_limit_k_max     32
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     11
_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 >
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     4112
_reflns_number_gt     2671
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0940
_refine_ls_R_factor_gt     0.0579
_refine_ls_wR_factor_gt     0.1367
_refine_ls_wR_factor_ref     0.1552
_refine_ls_goodness_of_fit_ref     1.018
_refine_ls_restrained_S_all     1.018
_refine_ls_number_reflns     4112
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0736P)²+0.3577P] 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     0.349
_refine_diff_density_min     -0.140
_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 (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SAINT (Siemens, 1996)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2003)
;
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 0.45657(13) 0.67700(3) 0.76685(8) 0.0850(3) Uani d . 1 . .
    O O2 0.6915(2) 0.85387(6) 0.88074(15) 0.0519(4) Uani d . 1 . .
    N N1 0.5321(3) 0.85694(8) 0.61201(19) 0.0494(5) Uani d . 1 . .
    C C16 0.7125(3) 0.88114(9) 0.9930(2) 0.0521(6) Uani d . 1 . .
    O O1 0.6508(2) 0.76281(7) 0.9880(2) 0.0724(6) Uani d . 1 . .
    C C10 0.6819(3) 0.87350(9) 0.5879(2) 0.0447(6) Uani d . 1 . .
    C C6 0.3402(3) 0.75625(9) 0.8833(2) 0.0483(6) Uani d . 1 . .
    O O3 0.6005(3) 0.88270(8) 1.0475(2) 0.0811(6) Uani d . 1 . .
    C C11 0.6356(3) 0.92094(10) 0.5281(2) 0.0518(6) Uani d . 1 . .
    N N2 0.4019(3) 0.89243(9) 0.5702(2) 0.0627(6) Uani d . 1 . .
    C C17 0.8850(3) 0.90815(9) 1.0357(2) 0.0501(6) Uani d . 1 . .
    N N3 0.4614(3) 0.93082(9) 0.5193(2) 0.0679(6) Uani d . 1 . .
    C C8 0.5253(3) 0.82806(9) 0.8302(2) 0.0479(6) Uani d . 1 . .
    H H8A 0.4285 0.8511 0.8316 0.058 Uiso calc R 1 . .
    C C22 1.0019(3) 0.90722(10) 0.9622(3) 0.0606(7) Uani d . 1 . .
    H H22A 0.9731 0.8894 0.8825 0.073 Uiso calc R 1 . .
    C C15 0.8502(3) 0.85257(11) 0.6109(3) 0.0576(7) Uani d . 1 . .
    H H15A 0.8805 0.8207 0.6501 0.069 Uiso calc R 1 . .
    C C7 0.5192(3) 0.78034(9) 0.9101(2) 0.0493(6) Uani d . 1 . .
    C C9 0.5084(3) 0.81338(10) 0.6880(2) 0.0537(6) Uani d . 1 . .
    H H9A 0.5967 0.7877 0.6881 0.064 Uiso calc R 1 . .
    H H9B 0.3923 0.7986 0.6467 0.064 Uiso calc R 1 . .
    C C20 1.2093(4) 0.95912(10) 1.1248(3) 0.0649(8) Uani d . 1 . .
    C C5 0.2118(4) 0.78141(11) 0.9250(3) 0.0644(7) Uani d . 1 . .
    H H5A 0.2369 0.8132 0.9659 0.077 Uiso calc R 1 . .
    C C1 0.3004(4) 0.70910(10) 0.8229(3) 0.0597(7) Uani d . 1 . .
    C C14 0.9684(4) 0.88207(12) 0.5720(3) 0.0689(8) Uani d . 1 . .
    H H14A 1.0827 0.8698 0.5857 0.083 Uiso calc R 1 . .
    C C2 0.1361(5) 0.68742(13) 0.8019(3) 0.0889(11) Uani d . 1 . .
    H H2B 0.1093 0.6560 0.7591 0.107 Uiso calc R 1 . .
    C C18 0.9309(4) 0.93510(11) 1.1532(3) 0.0678(8) Uani d . 1 . .
    H H18A 0.8530 0.9365 1.2032 0.081 Uiso calc R 1 . .
    C C12 0.7585(4) 0.94992(11) 0.4889(3) 0.0681(8) Uani d . 1 . .
    H H12A 0.7290 0.9816 0.4483 0.082 Uiso calc R 1 . .
    C C13 0.9234(4) 0.92969(12) 0.5129(3) 0.0703(8) Uani d . 1 . .
    H H13A 1.0088 0.9483 0.4890 0.084 Uiso calc R 1 . .
    C C19 1.0918(4) 0.95997(11) 1.1968(3) 0.0745(9) Uani d . 1 . .
    H H19A 1.1214 0.9777 1.2766 0.089 Uiso calc R 1 . .
    C C21 1.1613(4) 0.93279(11) 1.0071(3) 0.0698(8) Uani d . 1 . .
    H H21A 1.2383 0.9322 0.9563 0.084 Uiso calc R 1 . .
    C C23 1.3858(4) 0.98627(13) 1.1738(3) 0.0903(11) Uani d . 1 . .
    H H23A 1.4513 0.9809 1.1124 0.135 Uiso calc R 1 . .
    H H23B 1.4519 0.9730 1.2591 0.135 Uiso calc R 1 . .
    H H23C 1.3663 1.0222 1.1812 0.135 Uiso calc R 1 . .
    C C4 0.0476(4) 0.75943(16) 0.9057(4) 0.0883(11) Uani d . 1 . .
    H H4B -0.0379 0.7762 0.9338 0.106 Uiso calc R 1 . .
    C C3 0.0112(5) 0.71282(17) 0.8449(4) 0.1012(13) Uani d . 1 . .
    H H3B -0.0994 0.6980 0.8325 0.121 Uiso calc R 1 . .
_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 . 1.744(3) ?
    O2 C16 . 1.353(3) ?
    O2 C8 . 1.429(3) ?
    N1 N2 . 1.357(3) ?
    N1 C10 . 1.360(3) ?
    N1 C9 . 1.441(3) ?
    C16 O3 . 1.200(3) ?
    C16 C17 . 1.480(3) ?
    O1 C7 . 1.204(3) ?
    C10 C11 . 1.390(3) ?
    C10 C15 . 1.392(3) ?
    C6 C1 . 1.381(4) ?
    C6 C5 . 1.392(4) ?
    C6 C7 . 1.498(3) ?
    C11 N3 . 1.380(3) ?
    C11 C12 . 1.394(4) ?
    N2 N3 . 1.296(3) ?
    C17 C18 . 1.379(4) ?
    C17 C22 . 1.382(3) ?
    C8 C7 . 1.517(3) ?
    C8 C9 . 1.521(3) ?
    C8 H8A . 0.9800 ?
    C22 C21 . 1.378(4) ?
    C22 H22A . 0.9300 ?
    C15 C14 . 1.371(4) ?
    C15 H15A . 0.9300 ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C20 C21 . 1.372(4) ?
    C20 C19 . 1.374(4) ?
    C20 C23 . 1.512(4) ?
    C5 C4 . 1.379(4) ?
    C5 H5A . 0.9300 ?
    C1 C2 . 1.374(4) ?
    C14 C13 . 1.391(4) ?
    C14 H14A . 0.9300 ?
    C2 C3 . 1.381(5) ?
    C2 H2B . 0.9300 ?
    C18 C19 . 1.378(4) ?
    C18 H18A . 0.9300 ?
    C12 C13 . 1.359(4) ?
    C12 H12A . 0.9300 ?
    C13 H13A . 0.9300 ?
    C19 H19A . 0.9300 ?
    C21 H21A . 0.9300 ?
    C23 H23A . 0.9600 ?
    C23 H23B . 0.9600 ?
    C23 H23C . 0.9600 ?
    C4 C3 . 1.367(5) ?
    C4 H4B . 0.9300 ?
    C3 H3B . 0.9300 ?
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
    C16 O2 C8 . . 115.37(18) ?
    N2 N1 C10 . . 109.96(19) ?
    N2 N1 C9 . . 120.5(2) ?
    C10 N1 C9 . . 128.9(2) ?
    O3 C16 O2 . . 122.2(2) ?
    O3 C16 C17 . . 125.9(2) ?
    O2 C16 C17 . . 111.9(2) ?
    N1 C10 C11 . . 104.3(2) ?
    N1 C10 C15 . . 133.4(2) ?
    C11 C10 C15 . . 122.3(2) ?
    C1 C6 C5 . . 119.0(2) ?
    C1 C6 C7 . . 122.1(2) ?
    C5 C6 C7 . . 118.9(2) ?
    N3 C11 C10 . . 108.4(2) ?
    N3 C11 C12 . . 130.9(3) ?
    C10 C11 C12 . . 120.7(2) ?
    N3 N2 N1 . . 109.2(2) ?
    C18 C17 C22 . . 118.8(3) ?
    C18 C17 C16 . . 118.9(2) ?
    C22 C17 C16 . . 122.3(2) ?
    N2 N3 C11 . . 108.2(2) ?
    O2 C8 C7 . . 111.28(19) ?
    O2 C8 C9 . . 106.32(18) ?
    C7 C8 C9 . . 109.72(19) ?
    O2 C8 H8A . . 109.8 ?
    C7 C8 H8A . . 109.8 ?
    C9 C8 H8A . . 109.8 ?
    C21 C22 C17 . . 119.9(3) ?
    C21 C22 H22A . . 120.0 ?
    C17 C22 H22A . . 120.0 ?
    C14 C15 C10 . . 115.6(3) ?
    C14 C15 H15A . . 122.2 ?
    C10 C15 H15A . . 122.2 ?
    O1 C7 C6 . . 122.7(2) ?
    O1 C7 C8 . . 121.8(2) ?
    C6 C7 C8 . . 115.5(2) ?
    N1 C9 C8 . . 111.6(2) ?
    N1 C9 H9A . . 109.3 ?
    C8 C9 H9A . . 109.3 ?
    N1 C9 H9B . . 109.3 ?
    C8 C9 H9B . . 109.3 ?
    H9A C9 H9B . . 108.0 ?
    C21 C20 C19 . . 117.8(3) ?
    C21 C20 C23 . . 121.2(3) ?
    C19 C20 C23 . . 121.0(3) ?
    C4 C5 C6 . . 120.3(3) ?
    C4 C5 H5A . . 119.9 ?
    C6 C5 H5A . . 119.9 ?
    C2 C1 C6 . . 120.9(3) ?
    C2 C1 Cl1 . . 118.9(3) ?
    C6 C1 Cl1 . . 120.2(2) ?
    C15 C14 C13 . . 122.3(3) ?
    C15 C14 H14A . . 118.8 ?
    C13 C14 H14A . . 118.8 ?
    C1 C2 C3 . . 119.2(3) ?
    C1 C2 H2B . . 120.4 ?
    C3 C2 H2B . . 120.4 ?
    C19 C18 C17 . . 120.3(3) ?
    C19 C18 H18A . . 119.9 ?
    C17 C18 H18A . . 119.9 ?
    C13 C12 C11 . . 116.9(3) ?
    C13 C12 H12A . . 121.6 ?
    C11 C12 H12A . . 121.6 ?
    C12 C13 C14 . . 122.1(3) ?
    C12 C13 H13A . . 118.9 ?
    C14 C13 H13A . . 118.9 ?
    C20 C19 C18 . . 121.4(3) ?
    C20 C19 H19A . . 119.3 ?
    C18 C19 H19A . . 119.3 ?
    C20 C21 C22 . . 121.8(3) ?
    C20 C21 H21A . . 119.1 ?
    C22 C21 H21A . . 119.1 ?
    C20 C23 H23A . . 109.5 ?
    C20 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C20 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C3 C4 C5 . . 119.6(3) ?
    C3 C4 H4B . . 120.2 ?
    C5 C4 H4B . . 120.2 ?
    C4 C3 C2 . . 121.0(3) ?
    C4 C3 H3B . . 119.5 ?
    C2 C3 H3B . . 119.5 ?
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 O2 C16 O3 . . . . 1.4(3) ?
    C8 O2 C16 C17 . . . . -177.87(19) ?
    N2 N1 C10 C11 . . . . -0.5(3) ?
    C9 N1 C10 C11 . . . . -170.9(2) ?
    N2 N1 C10 C15 . . . . 179.8(3) ?
    C9 N1 C10 C15 . . . . 9.4(4) ?
    N1 C10 C11 N3 . . . . 0.2(3) ?
    C15 C10 C11 N3 . . . . 179.9(2) ?
    N1 C10 C11 C12 . . . . 179.9(2) ?
    C15 C10 C11 C12 . . . . -0.4(4) ?
    C10 N1 N2 N3 . . . . 0.6(3) ?
    C9 N1 N2 N3 . . . . 171.9(2) ?
    O3 C16 C17 C18 . . . . 4.8(4) ?
    O2 C16 C17 C18 . . . . -176.0(2) ?
    O3 C16 C17 C22 . . . . -175.4(3) ?
    O2 C16 C17 C22 . . . . 3.8(3) ?
    N1 N2 N3 C11 . . . . -0.4(3) ?
    C10 C11 N3 N2 . . . . 0.1(3) ?
    C12 C11 N3 N2 . . . . -179.5(3) ?
    C16 O2 C8 C7 . . . . -76.5(2) ?
    C16 O2 C8 C9 . . . . 164.1(2) ?
    C18 C17 C22 C21 . . . . 0.2(4) ?
    C16 C17 C22 C21 . . . . -179.6(2) ?
    N1 C10 C15 C14 . . . . -179.6(2) ?
    C11 C10 C15 C14 . . . . 0.7(4) ?
    C1 C6 C7 O1 . . . . -66.6(3) ?
    C5 C6 C7 O1 . . . . 111.1(3) ?
    C1 C6 C7 C8 . . . . 112.1(3) ?
    C5 C6 C7 C8 . . . . -70.2(3) ?
    O2 C8 C7 O1 . . . . -12.9(3) ?
    C9 C8 C7 O1 . . . . 104.5(3) ?
    O2 C8 C7 C6 . . . . 168.29(19) ?
    C9 C8 C7 C6 . . . . -74.3(3) ?
    N2 N1 C9 C8 . . . . -74.9(3) ?
    C10 N1 C9 C8 . . . . 94.6(3) ?
    O2 C8 C9 N1 . . . . -53.5(3) ?
    C7 C8 C9 N1 . . . . -174.0(2) ?
    C1 C6 C5 C4 . . . . -0.1(4) ?
    C7 C6 C5 C4 . . . . -177.9(2) ?
    C5 C6 C1 C2 . . . . 1.0(4) ?
    C7 C6 C1 C2 . . . . 178.7(2) ?
    C5 C6 C1 Cl1 . . . . 178.87(19) ?
    C7 C6 C1 Cl1 . . . . -3.4(3) ?
    C10 C15 C14 C13 . . . . -0.3(4) ?
    C6 C1 C2 C3 . . . . -1.6(5) ?
    Cl1 C1 C2 C3 . . . . -179.5(2) ?
    C22 C17 C18 C19 . . . . -0.9(4) ?
    C16 C17 C18 C19 . . . . 178.9(2) ?
    N3 C11 C12 C13 . . . . 179.2(3) ?
    C10 C11 C12 C13 . . . . -0.4(4) ?
    C11 C12 C13 C14 . . . . 0.8(4) ?
    C15 C14 C13 C12 . . . . -0.5(5) ?
    C21 C20 C19 C18 . . . . 0.3(4) ?
    C23 C20 C19 C18 . . . . -179.7(3) ?
    C17 C18 C19 C20 . . . . 0.6(4) ?
    C19 C20 C21 C22 . . . . -0.9(4) ?
    C23 C20 C21 C22 . . . . 179.0(3) ?
    C17 C22 C21 C20 . . . . 0.7(4) ?
    C6 C5 C4 C3 . . . . -0.2(5) ?
    C5 C4 C3 C2 . . . . -0.3(5) ?
    C1 C2 C3 C4 . . . . 1.2(5) ?
