##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-04-11
_journal_date_accepted     2010-05-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      6
_journal_page_first     o1506
_journal_page_last     o1506
_journal_paper_category     QO
_journal_coeditor_code     BT5245
_publ_contact_author_name     ' M.N. Ponnuswamy '
_publ_contact_author_address
;   Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai - 600 025
    India
;
_publ_contact_author_email     'mnpsy2004@yahoo.com'
_publ_contact_author_fax     '+9144 22352494'
_publ_contact_author_phone     '+9144 22300122'
_publ_section_title
;
3,5-dimethyl-1-chloroacetyl-2,6-bis(2-chlorophenyl)piperidin-4-one oxime
;
loop_
    _publ_author_name
    _publ_author_address
    'K. Ravichandran'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
    'P. Ramesh '
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
    'M. Rani'
;
    Department of Chemistry
    Annamalai University
    Annamalainagar 608 002
    Tamil Nadu
    India
;
    'S. Kabilan'
;
    Department of Chemistry
    Annamalai University
    Annamalainagar 608 002
    Tamil Nadu
    India
;
    'M. N. Ponnuswamy'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-chloroacetyl-2,6-bis(2-chlorophenyl)-3,5-dimethyl-piperidin-4-one oxime
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C21 H21 Cl3 N2 O2'
_chemical_formula_sum     'C21 H21 Cl3 N2 O2'
_chemical_formula_iupac     'C21 H21 Cl3 N2 O2'
_chemical_formula_weight     439.75
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C c'
_symmetry_space_group_name_Hall     'C -2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x, -y, z+1/2'
    'x+1/2, y+1/2, z'
    'x+1/2, -y+1/2, z+1/2'
_cell_length_a     9.8147(6)
_cell_length_b     15.5929(11)
_cell_length_c     13.9498(9)
_cell_angle_alpha     90.00
_cell_angle_beta     93.529(4)
_cell_angle_gamma     90.00
_cell_volume     2130.8(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1231
_cell_measurement_theta_min     2.46
_cell_measurement_theta_max     28.34
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.23
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.371
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     912
_exptl_absorpt_coefficient_mu     0.449
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.903
_exptl_absorpt_correction_T_max     0.927
_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 APEXII area-detector diffractometer'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10047
_diffrn_reflns_av_R_equivalents     0.0194
_diffrn_reflns_av_sigmaI/netI     0.0272
_diffrn_reflns_theta_min     2.46
_diffrn_reflns_theta_max     28.34
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -18
_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 >
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     4689
_reflns_number_gt     4181
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0368
_refine_ls_R_factor_gt     0.0306
_refine_ls_wR_factor_gt     0.0728
_refine_ls_wR_factor_ref     0.0764
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.027
_refine_ls_number_reflns     4689
_refine_ls_number_parameters     255
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0346P)²+0.6047P] 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     0.202
_refine_diff_density_min     -0.182
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 2045 Friedel pairs'
_refine_ls_abs_structure_Flack     0.04(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     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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 0.88541(8) 0.18026(6) 0.71303(5) 0.0929(3) Uani d . 1 . .
    Cl Cl2 0.40087(5) 0.06564(4) 0.47110(4) 0.05560(15) Uani d . 1 . .
    Cl Cl3 1.07034(7) -0.00744(6) 0.60948(5) 0.0826(2) Uani d . 1 . .
    O O1 0.57421(15) 0.18007(9) 0.60868(9) 0.0470(3) Uani d . 1 . .
    O O2 0.91903(18) 0.31451(10) 0.26625(12) 0.0605(4) Uani d . 1 . .
    H H2A 0.9746 0.3323 0.2295 0.091 Uiso calc R 1 . .
    N N1 0.71338(13) 0.12798(9) 0.49843(9) 0.0296(3) Uani d . 1 . .
    C C2 0.64401(17) 0.18068(11) 0.42143(12) 0.0328(3) Uani d . 1 . .
    H H2 0.5740 0.2141 0.4519 0.039 Uiso calc R 1 . .
    C C3 0.74830(19) 0.24562(13) 0.38710(13) 0.0400(4) Uani d . 1 . .
    H H3 0.7049 0.2779 0.3332 0.048 Uiso calc R 1 . .
    C C4 0.87049(17) 0.19941(13) 0.35168(12) 0.0372(4) Uani d . 1 . .
    C C5 0.89159(17) 0.10640(13) 0.37891(12) 0.0365(4) Uani d . 1 . .
    H H5 0.8338 0.0725 0.3334 0.044 Uiso calc R 1 . .
    C C6 0.84595(16) 0.08546(12) 0.48021(11) 0.0326(4) Uani d . 1 . .
    H H6 0.9157 0.1072 0.5274 0.039 Uiso calc R 1 . .
    C C7 0.67616(17) 0.13972(11) 0.58982(12) 0.0334(4) Uani d . 1 . .
    C C8 0.7634(2) 0.10242(15) 0.67283(13) 0.0480(5) Uani d . 1 . .
    H H8A 0.8093 0.0511 0.6523 0.058 Uiso calc R 1 . .
    H H8B 0.7066 0.0870 0.7247 0.058 Uiso calc R 1 . .
    C C9 0.56989(17) 0.12926(12) 0.34100(11) 0.0343(4) Uani d . 1 . .
    C C10 0.45857(18) 0.07723(13) 0.35647(13) 0.0403(4) Uani d . 1 . .
    C C11 0.3877(2) 0.03212(19) 0.28473(16) 0.0584(6) Uani d . 1 . .
    H H11 0.3146 -0.0027 0.2987 0.070 Uiso calc R 1 . .
    C C12 0.4266(2) 0.0394(2) 0.19198(18) 0.0749(8) Uani d . 1 . .
    H H12 0.3798 0.0094 0.1427 0.090 Uiso calc R 1 . .
    C C13 0.5331(2) 0.0905(2) 0.17247(14) 0.0668(7) Uani d . 1 . .
    H H13 0.5585 0.0956 0.1096 0.080 Uiso calc R 1 . .
    C C14 0.6050(2) 0.13518(15) 0.24530(13) 0.0467(5) Uani d . 1 . .
    H H14 0.6779 0.1698 0.2303 0.056 Uiso calc R 1 . .
    C C15 0.7918(3) 0.30940(15) 0.46641(19) 0.0625(6) Uani d . 1 . .
    H H15A 0.8360 0.2792 0.5196 0.094 Uiso calc R 1 . .
    H H15B 0.7127 0.3386 0.4873 0.094 Uiso calc R 1 . .
    H H15C 0.8539 0.3504 0.4421 0.094 Uiso calc R 1 . .
    N N16 0.95359(17) 0.23024(11) 0.29455(11) 0.0465(4) Uani d . 1 . .
    C C17 1.0382(2) 0.07602(18) 0.36986(17) 0.0626(7) Uani d . 1 . .
    H H17A 1.0663 0.0894 0.3069 0.094 Uiso calc R 1 . .
    H H17B 1.0430 0.0152 0.3799 0.094 Uiso calc R 1 . .
    H H17C 1.0974 0.1044 0.4172 0.094 Uiso calc R 1 . .
    C C18 0.83630(18) -0.01119(13) 0.49265(12) 0.0383(4) Uani d . 1 . .
    C C19 0.9322(2) -0.05775(16) 0.54924(15) 0.0545(6) Uani d . 1 . .
    C C20 0.9212(3) -0.14576(19) 0.5596(2) 0.0722(8) Uani d . 1 . .
    H H20 0.9846 -0.1754 0.5993 0.087 Uiso calc R 1 . .
    C C21 0.8168(3) -0.18886(17) 0.5115(2) 0.0773(9) Uani d . 1 . .
    H H21 0.8093 -0.2479 0.5186 0.093 Uiso calc R 1 . .
    C C22 0.7226(3) -0.14545(15) 0.4525(2) 0.0633(6) Uani d . 1 . .
    H H22 0.6528 -0.1751 0.4187 0.076 Uiso calc R 1 . .
    C C23 0.7326(2) -0.05725(13) 0.44401(14) 0.0442(4) Uani d . 1 . .
    H H23 0.6682 -0.0281 0.4047 0.053 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 C8 . 1.772(2) ?
    Cl2 C10 . 1.7383(18) ?
    Cl3 C19 . 1.738(3) ?
    O1 C7 . 1.224(2) ?
    O2 N16 . 1.408(2) ?
    O2 H2A . 0.8200 ?
    N1 C7 . 1.360(2) ?
    N1 C2 . 1.484(2) ?
    N1 C6 . 1.496(2) ?
    C2 C9 . 1.527(3) ?
    C2 C3 . 1.537(2) ?
    C2 H2 . 0.9800 ?
    C3 C4 . 1.508(2) ?
    C3 C15 . 1.529(3) ?
    C3 H3 . 0.9800 ?
    C4 N16 . 1.269(2) ?
    C4 C5 . 1.510(3) ?
    C5 C17 . 1.527(3) ?
    C5 C6 . 1.543(2) ?
    C5 H5 . 0.9800 ?
    C6 C18 . 1.521(3) ?
    C6 H6 . 0.9800 ?
    C7 C8 . 1.513(3) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.388(3) ?
    C9 C14 . 1.402(2) ?
    C10 C11 . 1.377(3) ?
    C11 C12 . 1.376(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.355(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.388(3) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C18 C23 . 1.388(3) ?
    C18 C19 . 1.394(3) ?
    C19 C20 . 1.385(4) ?
    C20 C21 . 1.367(4) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.377(4) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.384(3) ?
    C22 H22 . 0.9300 ?
    C23 H23 . 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
    N16 O2 H2A . . 109.5 ?
    C7 N1 C2 . . 117.79(13) ?
    C7 N1 C6 . . 120.37(13) ?
    C2 N1 C6 . . 119.18(12) ?
    N1 C2 C9 . . 114.70(14) ?
    N1 C2 C3 . . 107.79(14) ?
    C9 C2 C3 . . 114.42(14) ?
    N1 C2 H2 . . 106.4 ?
    C9 C2 H2 . . 106.4 ?
    C3 C2 H2 . . 106.4 ?
    C4 C3 C15 . . 110.84(17) ?
    C4 C3 C2 . . 110.21(15) ?
    C15 C3 C2 . . 111.38(15) ?
    C4 C3 H3 . . 108.1 ?
    C15 C3 H3 . . 108.1 ?
    C2 C3 H3 . . 108.1 ?
    N16 C4 C3 . . 125.40(18) ?
    N16 C4 C5 . . 115.98(16) ?
    C3 C4 C5 . . 118.42(14) ?
    C4 C5 C17 . . 113.10(16) ?
    C4 C5 C6 . . 112.98(14) ?
    C17 C5 C6 . . 109.75(15) ?
    C4 C5 H5 . . 106.9 ?
    C17 C5 H5 . . 106.9 ?
    C6 C5 H5 . . 106.9 ?
    N1 C6 C18 . . 111.03(13) ?
    N1 C6 C5 . . 111.49(13) ?
    C18 C6 C5 . . 109.74(14) ?
    N1 C6 H6 . . 108.2 ?
    C18 C6 H6 . . 108.2 ?
    C5 C6 H6 . . 108.2 ?
    O1 C7 N1 . . 122.74(16) ?
    O1 C7 C8 . . 117.68(15) ?
    N1 C7 C8 . . 119.57(15) ?
    C7 C8 Cl1 . . 108.57(15) ?
    C7 C8 H8A . . 110.0 ?
    Cl1 C8 H8A . . 110.0 ?
    C7 C8 H8B . . 110.0 ?
    Cl1 C8 H8B . . 110.0 ?
    H8A C8 H8B . . 108.4 ?
    C10 C9 C14 . . 115.36(17) ?
    C10 C9 C2 . . 122.45(14) ?
    C14 C9 C2 . . 122.10(17) ?
    C11 C10 C9 . . 123.57(17) ?
    C11 C10 Cl2 . . 115.90(15) ?
    C9 C10 Cl2 . . 120.52(14) ?
    C12 C11 C10 . . 118.9(2) ?
    C12 C11 H11 . . 120.5 ?
    C10 C11 H11 . . 120.5 ?
    C13 C12 C11 . . 120.0(2) ?
    C13 C12 H12 . . 120.0 ?
    C11 C12 H12 . . 120.0 ?
    C12 C13 C14 . . 120.8(2) ?
    C12 C13 H13 . . 119.6 ?
    C14 C13 H13 . . 119.6 ?
    C13 C14 C9 . . 121.3(2) ?
    C13 C14 H14 . . 119.3 ?
    C9 C14 H14 . . 119.3 ?
    C3 C15 H15A . . 109.5 ?
    C3 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C3 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C4 N16 O2 . . 112.12(16) ?
    C5 C17 H17A . . 109.5 ?
    C5 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C5 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C23 C18 C19 . . 117.14(19) ?
    C23 C18 C6 . . 120.39(16) ?
    C19 C18 C6 . . 122.42(19) ?
    C20 C19 C18 . . 121.4(2) ?
    C20 C19 Cl3 . . 117.39(19) ?
    C18 C19 Cl3 . . 121.19(18) ?
    C21 C20 C19 . . 119.8(2) ?
    C21 C20 H20 . . 120.1 ?
    C19 C20 H20 . . 120.1 ?
    C20 C21 C22 . . 120.5(2) ?
    C20 C21 H21 . . 119.8 ?
    C22 C21 H21 . . 119.8 ?
    C21 C22 C23 . . 119.4(3) ?
    C21 C22 H22 . . 120.3 ?
    C23 C22 H22 . . 120.3 ?
    C22 C23 C18 . . 121.7(2) ?
    C22 C23 H23 . . 119.1 ?
    C18 C23 H23 . . 119.1 ?
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
    C7 N1 C2 C9 . . . . -121.63(16) ?
    C6 N1 C2 C9 . . . . 76.79(18) ?
    C7 N1 C2 C3 . . . . 109.65(16) ?
    C6 N1 C2 C3 . . . . -51.92(19) ?
    N1 C2 C3 C4 . . . . 58.14(18) ?
    C9 C2 C3 C4 . . . . -70.73(19) ?
    N1 C2 C3 C15 . . . . -65.3(2) ?
    C9 C2 C3 C15 . . . . 165.81(17) ?
    C15 C3 C4 N16 . . . . -77.9(2) ?
    C2 C3 C4 N16 . . . . 158.32(18) ?
    C15 C3 C4 C5 . . . . 107.4(2) ?
    C2 C3 C4 C5 . . . . -16.4(2) ?
    N16 C4 C5 C17 . . . . 24.7(2) ?
    C3 C4 C5 C17 . . . . -160.10(18) ?
    N16 C4 C5 C6 . . . . 150.15(16) ?
    C3 C4 C5 C6 . . . . -34.6(2) ?
    C7 N1 C6 C18 . . . . 77.29(19) ?
    C2 N1 C6 C18 . . . . -121.62(16) ?
    C7 N1 C6 C5 . . . . -160.01(15) ?
    C2 N1 C6 C5 . . . . 1.1(2) ?
    C4 C5 C6 N1 . . . . 42.4(2) ?
    C17 C5 C6 N1 . . . . 169.59(18) ?
    C4 C5 C6 C18 . . . . 165.79(15) ?
    C17 C5 C6 C18 . . . . -67.0(2) ?
    C2 N1 C7 O1 . . . . 12.7(2) ?
    C6 N1 C7 O1 . . . . 174.07(17) ?
    C2 N1 C7 C8 . . . . -166.86(16) ?
    C6 N1 C7 C8 . . . . -5.5(2) ?
    O1 C7 C8 Cl1 . . . . -88.46(18) ?
    N1 C7 C8 Cl1 . . . . 91.14(18) ?
    N1 C2 C9 C10 . . . . 64.5(2) ?
    C3 C2 C9 C10 . . . . -170.16(16) ?
    N1 C2 C9 C14 . . . . -119.16(18) ?
    C3 C2 C9 C14 . . . . 6.2(2) ?
    C14 C9 C10 C11 . . . . 1.6(3) ?
    C2 C9 C10 C11 . . . . 178.1(2) ?
    C14 C9 C10 Cl2 . . . . -178.56(15) ?
    C2 C9 C10 Cl2 . . . . -2.0(2) ?
    C9 C10 C11 C12 . . . . -1.1(4) ?
    Cl2 C10 C11 C12 . . . . 179.0(2) ?
    C10 C11 C12 C13 . . . . 0.0(4) ?
    C11 C12 C13 C14 . . . . 0.6(4) ?
    C12 C13 C14 C9 . . . . -0.1(4) ?
    C10 C9 C14 C13 . . . . -1.0(3) ?
    C2 C9 C14 C13 . . . . -177.52(19) ?
    C3 C4 N16 O2 . . . . -0.2(3) ?
    C5 C4 N16 O2 . . . . 174.59(16) ?
    N1 C6 C18 C23 . . . . 52.7(2) ?
    C5 C6 C18 C23 . . . . -71.05(19) ?
    N1 C6 C18 C19 . . . . -129.93(16) ?
    C5 C6 C18 C19 . . . . 106.36(18) ?
    C23 C18 C19 C20 . . . . -2.6(3) ?
    C6 C18 C19 C20 . . . . 179.90(18) ?
    C23 C18 C19 Cl3 . . . . 177.34(14) ?
    C6 C18 C19 Cl3 . . . . -0.2(2) ?
    C18 C19 C20 C21 . . . . 1.9(3) ?
    Cl3 C19 C20 C21 . . . . -178.02(19) ?
    C19 C20 C21 C22 . . . . 0.2(4) ?
    C20 C21 C22 C23 . . . . -1.5(4) ?
    C21 C22 C23 C18 . . . . 0.7(3) ?
    C19 C18 C23 C22 . . . . 1.3(3) ?
    C6 C18 C23 C22 . . . . 178.83(17) ?
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
    O2 H2A O1 4_554 0.82 2.01 2.7515(18) 150.3
    C12 H12 Cl2 2_554 0.93 2.68 3.485(3) 144.8
    C20 H20 O1 3_545 0.93 2.42 3.158(3) 136.3
