##############################################################################
###                                                                        ###
###        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 # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2008-11-15
_journal_date_accepted     2008-11-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      1
_journal_page_first     o11
_journal_page_last     o11
_journal_paper_category     QO
_journal_coeditor_code     CI2726
_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
;\
1-Dichloroacetyl-r-2,c-6-bis(4-methoxyphenyl)-c-3,\
t-3-dimethylpiperidin-4-one
;
loop_
    _publ_author_name
    _publ_author_address
    'M. Thenmozhi'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
    'S. Ponnuswamy'
;
    Department of Chemistry
    Government Arts College (Autonomous)
    Coimbatore 641 018
    India
;
    'V. Mohanraj'
;
    Department of Chemistry
    Government Arts College (Autonomous)
    Coimbatore 641 018
    India
;
    'R. Vijayalakshmi'
;
   Department of Chemistry
   Queen Mary's College (Autonomous)
   Chennai 600 004
   India
;
    'M. N. Ponnuswamy'
;
    Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
data_I
_chemical_name_systematic
;
1-Dichloroacetyl-r-2,c-6-bis(4-methoxyphenyl)-c-3,t-3-dimethylpiperidin-4-one
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C23 H25 Cl2 N O4'
_chemical_formula_sum     'C23 H25 Cl2 N O4'
_chemical_formula_iupac     'C23 H25 Cl2 N O4'
_chemical_formula_weight     450.34
_chemical_melting_point     ?
_chemical_melting_point_gt     377
_chemical_melting_point_lt     379
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2/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'
    '-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     23.6295(9)
_cell_length_b     10.3999(4)
_cell_length_c     19.2617(9)
_cell_angle_alpha     90.00
_cell_angle_beta     107.7340(10)
_cell_angle_gamma     90.00
_cell_volume     4508.5(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     6905
_cell_measurement_theta_min     2.2
_cell_measurement_theta_max     30.6
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.327
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1888
_exptl_absorpt_coefficient_mu     0.317
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2001)'
_exptl_absorpt_correction_T_min     0.911
_exptl_absorpt_correction_T_max     0.939
_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 Kappa APEXII area-detector'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     29354
_diffrn_reflns_av_R_equivalents     0.0310
_diffrn_reflns_av_sigmaI/netI     0.0318
_diffrn_reflns_theta_min     2.16
_diffrn_reflns_theta_max     30.61
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -32
_diffrn_reflns_limit_h_max     33
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     27
_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     6905
_reflns_number_gt     4138
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0989
_refine_ls_R_factor_gt     0.0564
_refine_ls_wR_factor_gt     0.1513
_refine_ls_wR_factor_ref     0.1836
_refine_ls_goodness_of_fit_ref     1.005
_refine_ls_restrained_S_all     1.005
_refine_ls_number_reflns     6905
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0869P)²+2.9239P] 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     0.596
_refine_diff_density_min     -0.631
_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, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXS97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) 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 0.18029(3) 0.52254(7) 0.14172(4) 0.0790(2) Uani d . 1 . .
    Cl Cl2 0.26274(4) 0.62339(11) 0.07261(4) 0.1127(4) Uani d . 1 . .
    O O1 0.26407(7) 0.74756(16) 0.21261(9) 0.0635(4) Uani d . 1 . .
    O O2 0.56012(6) 0.89254(16) 0.36906(9) 0.0604(4) Uani d . 1 . .
    O O3 0.37036(9) 0.4204(2) 0.48165(10) 0.0798(6) Uani d . 1 . .
    O O4 0.48349(7) 0.30777(15) 0.10880(9) 0.0592(4) Uani d . 1 . .
    N N1 0.31916(6) 0.58476(15) 0.27717(8) 0.0402(3) Uani d . 1 . .
    C C2 0.33601(8) 0.66580(19) 0.34377(10) 0.0407(4) Uani d . 1 . .
    H H2 0.3092 0.7400 0.3325 0.049 Uiso calc R 1 . .
    C C3 0.32172(8) 0.5947(2) 0.40675(11) 0.0481(5) Uani d . 1 . .
    C C4 0.35641(9) 0.4707(2) 0.42265(12) 0.0530(5) Uani d . 1 . .
    C C5 0.37393(9) 0.4121(2) 0.36076(12) 0.0521(5) Uani d . 1 . .
    H H5A 0.3721 0.3194 0.3651 0.063 Uiso calc R 1 . .
    H H5B 0.4151 0.4343 0.3676 0.063 Uiso calc R 1 . .
    C C6 0.33818(8) 0.44832(19) 0.28249(11) 0.0435(4) Uani d . 1 . .
    H H6 0.3023 0.3950 0.2685 0.052 Uiso calc R 1 . .
    C C7 0.28061(8) 0.6362(2) 0.21725(11) 0.0460(4) Uani d . 1 . .
    C C8 0.25568(9) 0.5486(2) 0.15090(12) 0.0550(5) Uani d . 1 . .
    H H8 0.2771 0.4665 0.1587 0.066 Uiso calc R 1 . .
    C C9 0.39837(8) 0.72041(18) 0.35651(10) 0.0402(4) Uani d . 1 . .
    C C10 0.40476(8) 0.81147(19) 0.30699(10) 0.0431(4) Uani d . 1 . .
    H H10 0.3716 0.8357 0.2689 0.052 Uiso calc R 1 . .
    C C11 0.45865(9) 0.8669(2) 0.31249(11) 0.0476(5) Uani d . 1 . .
    H H11 0.4616 0.9282 0.2786 0.057 Uiso calc R 1 . .
    C C12 0.50864(8) 0.83169(19) 0.36834(11) 0.0453(4) Uani d . 1 . .
    C C13 0.50374(8) 0.7419(2) 0.41826(11) 0.0475(5) Uani d . 1 . .
    H H13 0.5371 0.7176 0.4560 0.057 Uiso calc R 1 . .
    C C14 0.44863(8) 0.6872(2) 0.41224(11) 0.0474(5) Uani d . 1 . .
    H H14 0.4456 0.6268 0.4466 0.057 Uiso calc R 1 . .
    C C15 0.61272(11) 0.8573(4) 0.4232(2) 0.1002(11) Uani d . 1 . .
    H H15A 0.6096 0.8793 0.4703 0.150 Uiso calc R 1 . .
    H H15B 0.6457 0.9022 0.4154 0.150 Uiso calc R 1 . .
    H H15C 0.6188 0.7663 0.4210 0.150 Uiso calc R 1 . .
    C C16 0.25568(9) 0.5548(3) 0.38209(14) 0.0630(6) Uani d . 1 . .
    H H16A 0.2487 0.4941 0.3428 0.095 Uiso calc R 1 . .
    H H16B 0.2313 0.6293 0.3659 0.095 Uiso calc R 1 . .
    H H16C 0.2459 0.5160 0.4222 0.095 Uiso calc R 1 . .
    C C17 0.33296(11) 0.6809(3) 0.47360(12) 0.0646(6) Uani d . 1 . .
    H H17A 0.3258 0.6332 0.5128 0.097 Uiso calc R 1 . .
    H H17B 0.3067 0.7536 0.4621 0.097 Uiso calc R 1 . .
    H H17C 0.3734 0.7101 0.4881 0.097 Uiso calc R 1 . .
    C C18 0.37492(8) 0.41315(18) 0.23272(11) 0.0416(4) Uani d . 1 . .
    C C19 0.37935(9) 0.2855(2) 0.21607(12) 0.0498(5) Uani d . 1 . .
    H H19 0.3576 0.2247 0.2326 0.060 Uiso calc R 1 . .
    C C20 0.41538(9) 0.2454(2) 0.17531(12) 0.0507(5) Uani d . 1 . .
    H H20 0.4180 0.1587 0.1650 0.061 Uiso calc R 1 . .
    C C21 0.44721(8) 0.3353(2) 0.15026(11) 0.0458(4) Uani d . 1 . .
    C C22 0.44278(9) 0.4630(2) 0.16603(13) 0.0533(5) Uani d . 1 . .
    H H22 0.4640 0.5240 0.1488 0.064 Uiso calc R 1 . .
    C C23 0.40738(9) 0.5018(2) 0.20705(13) 0.0508(5) Uani d . 1 . .
    H H23 0.4052 0.5885 0.2177 0.061 Uiso calc R 1 . .
    C C24 0.49748(14) 0.1779(2) 0.10196(17) 0.0750(7) Uani d . 1 . .
    H H24A 0.5128 0.1402 0.1495 0.113 Uiso calc R 1 . .
    H H24B 0.5269 0.1721 0.0770 0.113 Uiso calc R 1 . .
    H H24C 0.4623 0.1326 0.0747 0.113 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 C8 . 1.757(2) ?
    Cl2 C8 . 1.749(2) ?
    O1 C7 . 1.217(2) ?
    O2 C12 . 1.368(2) ?
    O2 C15 . 1.406(3) ?
    O3 C4 . 1.202(3) ?
    O4 C21 . 1.368(2) ?
    O4 C24 . 1.406(3) ?
    N1 C7 . 1.344(2) ?
    N1 C6 . 1.483(2) ?
    N1 C2 . 1.484(2) ?
    C2 C9 . 1.528(2) ?
    C2 C3 . 1.544(3) ?
    C2 H2 . 0.98 ?
    C3 C4 . 1.508(3) ?
    C3 C17 . 1.524(3) ?
    C3 C16 . 1.543(3) ?
    C4 C5 . 1.505(3) ?
    C5 C6 . 1.534(3) ?
    C5 H5A . 0.97 ?
    C5 H5B . 0.97 ?
    C6 C18 . 1.521(3) ?
    C6 H6 . 0.98 ?
    C7 C8 . 1.533(3) ?
    C8 H8 . 0.98 ?
    C9 C14 . 1.380(3) ?
    C9 C10 . 1.385(3) ?
    C10 C11 . 1.372(3) ?
    C10 H10 . 0.93 ?
    C11 C12 . 1.383(3) ?
    C11 H11 . 0.93 ?
    C12 C13 . 1.370(3) ?
    C13 C14 . 1.393(3) ?
    C13 H13 . 0.93 ?
    C14 H14 . 0.93 ?
    C15 H15A . 0.96 ?
    C15 H15B . 0.96 ?
    C15 H15C . 0.96 ?
    C16 H16A . 0.96 ?
    C16 H16B . 0.96 ?
    C16 H16C . 0.96 ?
    C17 H17A . 0.96 ?
    C17 H17B . 0.96 ?
    C17 H17C . 0.96 ?
    C18 C19 . 1.377(3) ?
    C18 C23 . 1.383(3) ?
    C19 C20 . 1.387(3) ?
    C19 H19 . 0.93 ?
    C20 C21 . 1.376(3) ?
    C20 H20 . 0.93 ?
    C21 C22 . 1.373(3) ?
    C22 C23 . 1.374(3) ?
    C22 H22 . 0.93 ?
    C23 H23 . 0.93 ?
    C24 H24A . 0.96 ?
    C24 H24B . 0.96 ?
    C24 H24C . 0.96 ?
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
    C12 O2 C15 . . 117.99(19) ?
    C21 O4 C24 . . 117.58(18) ?
    C7 N1 C6 . . 123.51(16) ?
    C7 N1 C2 . . 116.70(15) ?
    C6 N1 C2 . . 119.19(15) ?
    N1 C2 C9 . . 109.97(14) ?
    N1 C2 C3 . . 109.99(16) ?
    C9 C2 C3 . . 118.89(16) ?
    N1 C2 H2 . . 105.7 ?
    C9 C2 H2 . . 105.7 ?
    C3 C2 H2 . . 105.7 ?
    C4 C3 C17 . . 112.76(18) ?
    C4 C3 C16 . . 105.59(19) ?
    C17 C3 C16 . . 108.54(17) ?
    C4 C3 C2 . . 109.49(15) ?
    C17 C3 C2 . . 111.01(18) ?
    C16 C3 C2 . . 109.25(17) ?
    O3 C4 C5 . . 120.7(2) ?
    O3 C4 C3 . . 122.7(2) ?
    C5 C4 C3 . . 116.68(17) ?
    C4 C5 C6 . . 118.50(17) ?
    C4 C5 H5A . . 107.7 ?
    C6 C5 H5A . . 107.7 ?
    C4 C5 H5B . . 107.7 ?
    C6 C5 H5B . . 107.7 ?
    H5A C5 H5B . . 107.1 ?
    N1 C6 C18 . . 113.94(15) ?
    N1 C6 C5 . . 111.57(16) ?
    C18 C6 C5 . . 108.14(15) ?
    N1 C6 H6 . . 107.6 ?
    C18 C6 H6 . . 107.6 ?
    C5 C6 H6 . . 107.6 ?
    O1 C7 N1 . . 124.06(19) ?
    O1 C7 C8 . . 118.08(18) ?
    N1 C7 C8 . . 117.85(18) ?
    C7 C8 Cl2 . . 109.96(16) ?
    C7 C8 Cl1 . . 107.21(15) ?
    Cl2 C8 Cl1 . . 110.00(12) ?
    C7 C8 H8 . . 109.9 ?
    Cl2 C8 H8 . . 109.9 ?
    Cl1 C8 H8 . . 109.9 ?
    C14 C9 C10 . . 117.29(17) ?
    C14 C9 C2 . . 126.23(17) ?
    C10 C9 C2 . . 116.48(16) ?
    C11 C10 C9 . . 121.84(18) ?
    C11 C10 H10 . . 119.1 ?
    C9 C10 H10 . . 119.1 ?
    C10 C11 C12 . . 120.10(19) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    O2 C12 C13 . . 124.98(18) ?
    O2 C12 C11 . . 115.57(18) ?
    C13 C12 C11 . . 119.45(18) ?
    C12 C13 C14 . . 119.78(18) ?
    C12 C13 H13 . . 120.1 ?
    C14 C13 H13 . . 120.1 ?
    C9 C14 C13 . . 121.55(19) ?
    C9 C14 H14 . . 119.2 ?
    C13 C14 H14 . . 119.2 ?
    O2 C15 H15A . . 109.5 ?
    O2 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    O2 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C3 C16 H16A . . 109.5 ?
    C3 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C3 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C3 C17 H17A . . 109.5 ?
    C3 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C3 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C19 C18 C23 . . 117.99(18) ?
    C19 C18 C6 . . 118.50(17) ?
    C23 C18 C6 . . 123.37(18) ?
    C18 C19 C20 . . 121.69(18) ?
    C18 C19 H19 . . 119.2 ?
    C20 C19 H19 . . 119.2 ?
    C21 C20 C19 . . 119.30(19) ?
    C21 C20 H20 . . 120.3 ?
    C19 C20 H20 . . 120.3 ?
    O4 C21 C22 . . 115.80(18) ?
    O4 C21 C20 . . 124.66(19) ?
    C22 C21 C20 . . 119.54(18) ?
    C21 C22 C23 . . 120.75(19) ?
    C21 C22 H22 . . 119.6 ?
    C23 C22 H22 . . 119.6 ?
    C22 C23 C18 . . 120.72(19) ?
    C22 C23 H23 . . 119.6 ?
    C18 C23 H23 . . 119.6 ?
    O4 C24 H24A . . 109.5 ?
    O4 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    O4 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
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
    C7 N1 C2 C9 . . . . -104.12(18) ?
    C6 N1 C2 C9 . . . . 84.47(19) ?
    C7 N1 C2 C3 . . . . 123.10(17) ?
    C6 N1 C2 C3 . . . . -48.31(19) ?
    N1 C2 C3 C4 . . . . 60.4(2) ?
    C9 C2 C3 C4 . . . . -67.6(2) ?
    N1 C2 C3 C17 . . . . -174.47(15) ?
    C9 C2 C3 C17 . . . . 57.5(2) ?
    N1 C2 C3 C16 . . . . -54.8(2) ?
    C9 C2 C3 C16 . . . . 177.18(18) ?
    C17 C3 C4 O3 . . . . 29.1(3) ?
    C16 C3 C4 O3 . . . . -89.2(3) ?
    C2 C3 C4 O3 . . . . 153.3(2) ?
    C17 C3 C4 C5 . . . . -150.11(19) ?
    C16 C3 C4 C5 . . . . 91.5(2) ?
    C2 C3 C4 C5 . . . . -26.0(2) ?
    O3 C4 C5 C6 . . . . 158.4(2) ?
    C3 C4 C5 C6 . . . . -22.3(3) ?
    C7 N1 C6 C18 . . . . 66.7(2) ?
    C2 N1 C6 C18 . . . . -122.54(17) ?
    C7 N1 C6 C5 . . . . -170.53(17) ?
    C2 N1 C6 C5 . . . . 0.3(2) ?
    C4 C5 C6 N1 . . . . 36.3(2) ?
    C4 C5 C6 C18 . . . . 162.32(18) ?
    C6 N1 C7 O1 . . . . 178.95(18) ?
    C2 N1 C7 O1 . . . . 7.9(3) ?
    C6 N1 C7 C8 . . . . -0.6(3) ?
    C2 N1 C7 C8 . . . . -171.63(16) ?
    O1 C7 C8 Cl2 . . . . 49.9(2) ?
    N1 C7 C8 Cl2 . . . . -130.51(17) ?
    O1 C7 C8 Cl1 . . . . -69.7(2) ?
    N1 C7 C8 Cl1 . . . . 109.92(18) ?
    N1 C2 C9 C14 . . . . -110.8(2) ?
    C3 C2 C9 C14 . . . . 17.3(3) ?
    N1 C2 C9 C10 . . . . 68.9(2) ?
    C3 C2 C9 C10 . . . . -163.05(18) ?
    C14 C9 C10 C11 . . . . 0.1(3) ?
    C2 C9 C10 C11 . . . . -179.62(18) ?
    C9 C10 C11 C12 . . . . 0.4(3) ?
    C15 O2 C12 C13 . . . . 2.6(3) ?
    C15 O2 C12 C11 . . . . -177.9(3) ?
    C10 C11 C12 O2 . . . . -179.95(18) ?
    C10 C11 C12 C13 . . . . -0.5(3) ?
    O2 C12 C13 C14 . . . . 179.43(19) ?
    C11 C12 C13 C14 . . . . 0.0(3) ?
    C10 C9 C14 C13 . . . . -0.6(3) ?
    C2 C9 C14 C13 . . . . 179.11(18) ?
    C12 C13 C14 C9 . . . . 0.5(3) ?
    N1 C6 C18 C19 . . . . -160.22(17) ?
    C5 C6 C18 C19 . . . . 75.1(2) ?
    N1 C6 C18 C23 . . . . 24.2(3) ?
    C5 C6 C18 C23 . . . . -100.5(2) ?
    C23 C18 C19 C20 . . . . 0.4(3) ?
    C6 C18 C19 C20 . . . . -175.39(19) ?
    C18 C19 C20 C21 . . . . -0.5(3) ?
    C24 O4 C21 C22 . . . . 169.2(2) ?
    C24 O4 C21 C20 . . . . -11.7(3) ?
    C19 C20 C21 O4 . . . . -179.0(2) ?
    C19 C20 C21 C22 . . . . 0.0(3) ?
    O4 C21 C22 C23 . . . . 179.7(2) ?
    C20 C21 C22 C23 . . . . 0.6(3) ?
    C21 C22 C23 C18 . . . . -0.7(4) ?
    C19 C18 C23 C22 . . . . 0.2(3) ?
    C6 C18 C23 C22 . . . . 175.8(2) ?
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
    C6 H6 O1 4_545 0.98 2.30 3.216(2) 155
    C13 H13 O3 5_666 0.93 2.58 3.453(3) 155
