##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, 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     'manual editing of form.cif'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2013-08-23
_journal_date_accepted     2013-12-13
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2014
_journal_volume     70
_journal_issue      2
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270113033817
_journal_coeditor_code     EM3064
_publ_contact_author_name     'Zhi Min Jin'
_publ_contact_author_address
;
College of Pharmaceutical Science
Zhejiang University of Technology
Hangzhou 310014, People's Republic of China
;
_publ_contact_author_email     zimichem@sina.com
_publ_contact_author_fax     '++86-571-88320320'
_publ_contact_author_phone     '++86-571-88320320'
_publ_section_title
;
A hydrogen-bonded three-component complex: bis(dicyclohexylammonium)
2,4-dichlorophenolate 2,4,6-trichlorophenolate 2,4-dichlorophenol
;
loop_
    _publ_author_name
    _publ_author_address
    'Xiao-Qing Cai'
;
College of Chemistry and Materials Engineering
Wenzhou University
Wenzhou 325035
People's Republic of China
;
    'Zhi Min Jin'
;
College of Pharmaceutical Sciences
Zhejiang University of Technology
Hangzhou 310014
People's Republic of China
;
_publ_section_synopsis
;
Five molecules of three different achiral components of dicyclohexylammonium,
2,4-dichlorophenolate and 2,4,6-trichlorophenolate are held together by
O---H...N and O---H...O hydrogen bonds to form a chiral hydrogen-bonded ring.
A helical cylinder is established by the packing of the chiral hydrogen-bonded
rings along the c axis.
;
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 977068'
_chemical_name_systematic
;
Bis(dicyclohexylammonium) 2,4-dichlorophenolate 2,4,6-trichlorophenolate
2,4-dichlorophenol
;
_chemical_name_common     ?
_chemical_formula_moiety
                      '2(C12 H24 N+), C6 H3 Cl2 O -, C6 H2 Cl3 O -, C6 H4 Cl2 O'
_chemical_formula_sum     'C42 H57 Cl7 N2 O3'
_chemical_formula_iupac
                       '2C12 H24 N +, C6 H3 Cl2 O -, C6 H2 Cl3 O -, C6 H4 Cl2 O'
_chemical_formula_weight     886.05
_chemical_melting_point     ?
_space_group_crystal_system     tetragonal
_space_group_name_H-M_alt     'P 41 2 2'
_space_group_name_Hall     'P 4w 2c'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-y, x, z+1/4'
    '-x, -y, z+1/2'
    'y, -x, z+3/4'
    'x, -y, -z+1/2'
    'y, x, -z+3/4'
    '-x, y, -z'
    '-y, -x, -z+1/4'
_cell_length_a     10.6040(10)
_cell_length_b     10.6040(10)
_cell_length_c     39.960(9)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     4493.3(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2879
_cell_measurement_theta_min     2.11
_cell_measurement_theta_max     23.12
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.310
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1864
_exptl_absorpt_coefficient_mu     0.481
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.8932
_exptl_absorpt_correction_T_max     0.9179
_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     25411
_diffrn_reflns_av_R_equivalents     0.0163
_diffrn_reflns_av_sigmaI/netI     0.0332
_diffrn_reflns_theta_min     1.92
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -44
_diffrn_reflns_limit_l_max     49
_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     4422
_reflns_number_gt     3563
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0640
_refine_ls_R_factor_gt     0.0579
_refine_ls_wR_factor_gt     0.1447
_refine_ls_wR_factor_ref     0.1461
_refine_ls_goodness_of_fit_ref     1.099
_refine_ls_restrained_S_all     1.099
_refine_ls_number_reflns     4422
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0916P)²+0.0000P] 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     0.331
_refine_diff_density_min     -0.322
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                              'Flack & Bernardinelli (1999), 1763 Friedel pairs'
_refine_ls_abs_structure_Flack     0.00(9)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SMART (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 2000)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (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
    C C1 0.6792(4) 0.5410(4) 0.06619(8) 0.0659(10) Uani d . 1 1 . .
    H H1A 0.5885 0.5323 0.0682 0.079 Uiso calc R 1 1 . .
    H H1B 0.7173 0.4596 0.0708 0.079 Uiso calc R 1 1 . .
    C C2 0.7132(4) 0.5833(5) 0.03085(9) 0.0770(12) Uani d . 1 1 . .
    H H2A 0.6879 0.5186 0.0150 0.092 Uiso calc R 1 1 . .
    H H2B 0.6670 0.6597 0.0255 0.092 Uiso calc R 1 1 . .
    C C3 0.8515(4) 0.6076(5) 0.02726(10) 0.0828(13) Uani d . 1 1 . .
    H H3A 0.8685 0.6382 0.0048 0.099 Uiso calc R 1 1 . .
    H H3B 0.8970 0.5290 0.0302 0.099 Uiso calc R 1 1 . .
    C C4 0.8993(5) 0.7035(5) 0.05254(9) 0.0831(13) Uani d . 1 1 . .
    H H4A 0.8608 0.7849 0.0482 0.100 Uiso calc R 1 1 . .
    H H4B 0.9899 0.7126 0.0504 0.100 Uiso calc R 1 1 . .
    C C5 0.8664(4) 0.6600(4) 0.08825(9) 0.0662(10) Uani d . 1 1 . .
    H H5A 0.9116 0.5828 0.0934 0.079 Uiso calc R 1 1 . .
    H H5B 0.8921 0.7239 0.1042 0.079 Uiso calc R 1 1 . .
    C C6 0.7266(3) 0.6375(3) 0.09116(8) 0.0514(8) Uani d . 1 1 . .
    H H6 0.6838 0.7174 0.0864 0.062 Uiso calc R 1 1 . .
    C C7 0.7204(3) 0.6820(3) 0.15414(7) 0.0463(7) Uani d . 1 1 . .
    H H7 0.8117 0.6963 0.1545 0.056 Uiso calc R 1 1 . .
    C C8 0.6818(4) 0.6157(4) 0.18605(8) 0.0560(8) Uani d . 1 1 . .
    H H8A 0.7275 0.5368 0.1882 0.067 Uiso calc R 1 1 . .
    H H8B 0.5923 0.5968 0.1854 0.067 Uiso calc R 1 1 . .
    C C9 0.7108(5) 0.7006(5) 0.21589(10) 0.0770(12) Uani d . 1 1 . .
    H H9A 0.6829 0.6593 0.2362 0.092 Uiso calc R 1 1 . .
    H H9B 0.8013 0.7126 0.2175 0.092 Uiso calc R 1 1 . .
    C C10 0.6497(5) 0.8230(5) 0.21323(11) 0.0921(15) Uani d . 1 1 . .
    H H10A 0.6760 0.8754 0.2318 0.110 Uiso calc R 1 1 . .
    H H10B 0.5591 0.8118 0.2147 0.110 Uiso calc R 1 1 . .
    C C11 0.6814(5) 0.8900(4) 0.18044(10) 0.0789(12) Uani d . 1 1 . .
    H H11A 0.6326 0.9671 0.1789 0.095 Uiso calc R 1 1 . .
    H H11B 0.7700 0.9126 0.1804 0.095 Uiso calc R 1 1 . .
    C C12 0.6535(4) 0.8080(3) 0.15031(9) 0.0622(9) Uani d . 1 1 . .
    H H12A 0.6822 0.8498 0.1301 0.075 Uiso calc R 1 1 . .
    H H12B 0.5633 0.7945 0.1484 0.075 Uiso calc R 1 1 . .
    C C13 0.85606(19) 0.31031(18) 0.16520(4) 0.0455(7) Uani d G 1 1 . .
    C C14 0.9499(2) 0.38293(17) 0.18001(6) 0.0526(8) Uani d G 1 1 . .
    C C15 1.0078(2) 0.3418(2) 0.20925(6) 0.0667(11) Uani d G 1 1 . .
    H H15 1.0705 0.3904 0.2191 0.080 Uiso calc R 1 1 . .
    C C16 0.9719(2) 0.2281(2) 0.22368(5) 0.0701(11) Uani d G 1 1 . .
    C C17 0.8781(2) 0.1555(2) 0.20887(5) 0.0691(11) Uani d G 1 1 . .
    H H17 0.8541 0.0794 0.2185 0.083 Uiso calc R 1 1 . .
    C C18 0.8202(2) 0.19657(19) 0.17964(5) 0.0621(9) Uani d G 1 1 . .
    H H18 0.7574 0.1480 0.1697 0.074 Uiso calc R 1 1 . .
    C C19 0.1591(4) 0.8409(4) 0.1250 0.0694(15) Uani d S 1 2 . .
    C C20 0.2148(4) 0.8104(4) 0.09596(10) 0.0641(10) Uani d . 1 1 . .
    H H20 0.1924 0.8515 0.0763 0.077 Uiso calc R 1 1 . .
    C C21 0.3062(4) 0.7166(3) 0.09563(8) 0.0559(9) Uani d . 1 1 . .
    C C22 0.3481(3) 0.6519(3) 0.1250 0.0465(10) Uani d S 1 2 . .
    Cl Cl1 1.00087(10) 0.51891(9) 0.16186(3) 0.0741(3) Uani d . 1 1 . .
    Cl Cl2 1.04267(9) 0.17755(10) 0.25968(2) 0.0683(3) Uani d . 1 1 . .
    Cl Cl3 0.04269(8) 0.95731(8) 0.1250 0.0675(4) Uani d S 1 2 . .
    Cl Cl4 0.37592(10) 0.68113(10) 0.05872(2) 0.0688(3) Uani d . 1 1 . .
    N N1 0.6888(3) 0.5968(3) 0.12552(7) 0.0453(6) Uani d . 1 1 . .
    O O1 0.7965(2) 0.3526(2) 0.13720(5) 0.0470(5) Uani d . 1 1 . .
    O O2 0.4336(2) 0.5664(2) 0.1250 0.0505(7) Uani d S 1 2 . .
    H H1C 0.606(3) 0.591(3) 0.1252(8) 0.046(9) Uiso d . 1 1 . .
    H H1D 0.716(4) 0.519(4) 0.1312(9) 0.064(11) Uiso d . 1 1 . .
    H H1 0.725(3) 0.275(3) 0.1250 0.057(13) Uiso d S 1 2 . .
_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
    C1 C6 . 1.515(5) ?
    C1 C2 . 1.525(5) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.497(6) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.521(6) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C5 . 1.540(5) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 C6 . 1.506(5) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 N1 . 1.494(4) yes
    C6 H6 . 0.9800 ?
    C7 N1 . 1.495(4) yes
    C7 C8 . 1.513(5) ?
    C7 C12 . 1.520(5) ?
    C7 H7 . 0.9800 ?
    C8 C9 . 1.525(5) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.455(7) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.528(6) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C12 . 1.514(5) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 O1 . 1.361(2) yes
    C13 C14 . 1.3900 ?
    C13 C18 . 1.3900 ?
    C14 C15 . 1.3900 ?
    C14 Cl1 . 1.702(2) ?
    C15 C16 . 1.3900 ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.3900 ?
    C16 Cl2 . 1.7087(17) ?
    C17 C18 . 1.3900 ?
    C17 H17 . 0.9300 ?
    C18 H18 . 0.9300 ?
    C19 C20 8_665 1.342(5) ?
    C19 C20 . 1.342(5) yes
    C19 Cl3 . 1.745(6) ?
    C20 C21 . 1.389(6) yes
    C20 H20 . 0.9300 ?
    C21 C22 . 1.430(4) yes
    C21 Cl4 . 1.692(4) ?
    C22 O2 . 1.282(5) yes
    C22 C21 8_665 1.430(4) ?
    N1 H1C . 0.88(4) ?
    N1 H1D . 0.90(4) ?
    O1 H1 . 1.22(3) ?
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
    C6 C1 C2 . . 109.4(3) ?
    C6 C1 H1A . . 109.8 ?
    C2 C1 H1A . . 109.8 ?
    C6 C1 H1B . . 109.8 ?
    C2 C1 H1B . . 109.8 ?
    H1A C1 H1B . . 108.2 ?
    C3 C2 C1 . . 111.8(4) ?
    C3 C2 H2A . . 109.3 ?
    C1 C2 H2A . . 109.3 ?
    C3 C2 H2B . . 109.3 ?
    C1 C2 H2B . . 109.3 ?
    H2A C2 H2B . . 107.9 ?
    C2 C3 C4 . . 112.2(4) ?
    C2 C3 H3A . . 109.2 ?
    C4 C3 H3A . . 109.2 ?
    C2 C3 H3B . . 109.2 ?
    C4 C3 H3B . . 109.2 ?
    H3A C3 H3B . . 107.9 ?
    C3 C4 C5 . . 109.8(4) ?
    C3 C4 H4A . . 109.7 ?
    C5 C4 H4A . . 109.7 ?
    C3 C4 H4B . . 109.7 ?
    C5 C4 H4B . . 109.7 ?
    H4A C4 H4B . . 108.2 ?
    C6 C5 C4 . . 110.0(3) ?
    C6 C5 H5A . . 109.7 ?
    C4 C5 H5A . . 109.7 ?
    C6 C5 H5B . . 109.7 ?
    C4 C5 H5B . . 109.7 ?
    H5A C5 H5B . . 108.2 ?
    N1 C6 C5 . . 112.3(3) ?
    N1 C6 C1 . . 108.8(3) ?
    C5 C6 C1 . . 112.5(3) ?
    N1 C6 H6 . . 107.7 ?
    C5 C6 H6 . . 107.7 ?
    C1 C6 H6 . . 107.7 ?
    N1 C7 C8 . . 107.7(3) ?
    N1 C7 C12 . . 110.4(3) ?
    C8 C7 C12 . . 111.5(3) ?
    N1 C7 H7 . . 109.0 ?
    C8 C7 H7 . . 109.0 ?
    C12 C7 H7 . . 109.0 ?
    C7 C8 C9 . . 109.3(3) ?
    C7 C8 H8A . . 109.8 ?
    C9 C8 H8A . . 109.8 ?
    C7 C8 H8B . . 109.8 ?
    C9 C8 H8B . . 109.8 ?
    H8A C8 H8B . . 108.3 ?
    C10 C9 C8 . . 112.3(4) ?
    C10 C9 H9A . . 109.1 ?
    C8 C9 H9A . . 109.1 ?
    C10 C9 H9B . . 109.1 ?
    C8 C9 H9B . . 109.1 ?
    H9A C9 H9B . . 107.9 ?
    C9 C10 C11 . . 112.3(4) ?
    C9 C10 H10A . . 109.1 ?
    C11 C10 H10A . . 109.1 ?
    C9 C10 H10B . . 109.1 ?
    C11 C10 H10B . . 109.1 ?
    H10A C10 H10B . . 107.9 ?
    C12 C11 C10 . . 111.8(3) ?
    C12 C11 H11A . . 109.2 ?
    C10 C11 H11A . . 109.2 ?
    C12 C11 H11B . . 109.2 ?
    C10 C11 H11B . . 109.2 ?
    H11A C11 H11B . . 107.9 ?
    C11 C12 C7 . . 109.5(3) ?
    C11 C12 H12A . . 109.8 ?
    C7 C12 H12A . . 109.8 ?
    C11 C12 H12B . . 109.8 ?
    C7 C12 H12B . . 109.8 ?
    H12A C12 H12B . . 108.2 ?
    O1 C13 C14 . . 119.97(15) ?
    O1 C13 C18 . . 120.00(15) ?
    C14 C13 C18 . . 120.0 ?
    C13 C14 C15 . . 120.0 ?
    C13 C14 Cl1 . . 121.02(12) ?
    C15 C14 Cl1 . . 118.91(12) ?
    C16 C15 C14 . . 120.0 ?
    C16 C15 H15 . . 120.0 ?
    C14 C15 H15 . . 120.0 ?
    C15 C16 C17 . . 120.0 ?
    C15 C16 Cl2 . . 120.07(14) ?
    C17 C16 Cl2 . . 119.93(14) ?
    C18 C17 C16 . . 120.0 ?
    C18 C17 H17 . . 120.0 ?
    C16 C17 H17 . . 120.0 ?
    C17 C18 C13 . . 120.0 ?
    C17 C18 H18 . . 120.0 ?
    C13 C18 H18 . . 120.0 ?
    C20 C19 C20 8_665 . 122.4(6) ?
    C20 C19 Cl3 8_665 . 118.8(3) ?
    C20 C19 Cl3 . . 118.8(3) ?
    C19 C20 C21 . . 119.2(4) ?
    C19 C20 H20 . . 120.4 ?
    C21 C20 H20 . . 120.4 ?
    C20 C21 C22 . . 123.6(3) ?
    C20 C21 Cl4 . . 118.2(3) ?
    C22 C21 Cl4 . . 118.2(3) ?
    O2 C22 C21 . . 124.0(2) ?
    O2 C22 C21 . 8_665 124.0(2) ?
    C21 C22 C21 . 8_665 112.0(4) ?
    C6 N1 C7 . . 118.0(3) ?
    C6 N1 H1C . . 106(2) ?
    C7 N1 H1C . . 106(2) ?
    C6 N1 H1D . . 114(2) ?
    C7 N1 H1D . . 107(2) ?
    H1C N1 H1D . . 104(3) ?
    C13 O1 H1 . . 113.3(15) ?
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 . . . . 55.1(5) ?
    C1 C2 C3 C4 . . . . -56.1(6) ?
    C2 C3 C4 C5 . . . . 55.7(6) ?
    C3 C4 C5 C6 . . . . -55.7(5) ?
    C4 C5 C6 N1 . . . . -179.1(3) ?
    C4 C5 C6 C1 . . . . 57.8(5) ?
    C2 C1 C6 N1 . . . . 178.1(3) yes
    C2 C1 C6 C5 . . . . -56.8(5) ?
    N1 C7 C8 C9 . . . . -179.2(3) yes
    C12 C7 C8 C9 . . . . -57.9(4) ?
    C7 C8 C9 C10 . . . . 56.6(5) ?
    C8 C9 C10 C11 . . . . -54.6(5) ?
    C9 C10 C11 C12 . . . . 53.7(6) ?
    C10 C11 C12 C7 . . . . -53.8(5) ?
    N1 C7 C12 C11 . . . . 177.1(3) ?
    C8 C7 C12 C11 . . . . 57.4(4) ?
    O1 C13 C14 C15 . . . . 177.8(2) ?
    C18 C13 C14 C15 . . . . 0.0 ?
    O1 C13 C14 Cl1 . . . . -5.3(2) ?
    C18 C13 C14 Cl1 . . . . 176.9(2) ?
    C13 C14 C15 C16 . . . . 0.0 ?
    Cl1 C14 C15 C16 . . . . -177.0(2) ?
    C14 C15 C16 C17 . . . . 0.0 ?
    C14 C15 C16 Cl2 . . . . -179.8(2) ?
    C15 C16 C17 C18 . . . . 0.0 ?
    Cl2 C16 C17 C18 . . . . 179.8(2) ?
    C16 C17 C18 C13 . . . . 0.0 ?
    O1 C13 C18 C17 . . . . -177.8(2) ?
    C14 C13 C18 C17 . . . . 0.0 ?
    C20 C19 C20 C21 8_665 . . . 0.9(2) ?
    Cl3 C19 C20 C21 . . . . -179.1(2) ?
    C19 C20 C21 C22 . . . . -1.9(5) ?
    C19 C20 C21 Cl4 . . . . -179.4(2) ?
    C20 C21 C22 O2 . . . . -179.1(2) ?
    Cl4 C21 C22 O2 . . . . -1.6(3) ?
    C20 C21 C22 C21 . . . 8_665 0.9(2) ?
    Cl4 C21 C22 C21 . . . 8_665 178.4(3) ?
    C5 C6 N1 C7 . . . . 57.8(4) ?
    C1 C6 N1 C7 . . . . -177.0(3) yes
    C8 C7 N1 C6 . . . . -175.7(3) yes
    C12 C7 N1 C6 . . . . 62.3(4) ?
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
    _geom_hbond_publ_flag
    O1 H1 O1 8_665 1.22(3) 1.22(3) 2.439(4) 176(5) yes
    N1 H1C O2 . 0.88(4) 1.85(4) 2.726(4) 176(3) yes
    N1 H1D O1 . 0.90(4) 1.98(4) 2.868(4) 170(3) yes
