##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2018/1'
_journal_date_recd_electronic     2019-04-08
_journal_date_accepted     2019-04-10
_journal_name_full     'IUCrData'
_journal_year     2019
_journal_volume     4
_journal_issue      4
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314619004942
_journal_coeditor_code     SJ4202
_publ_contact_author_name     'Manuel A.S. Aquino'
_publ_contact_author_address
;
Department of Chemistry, St. Francis Xavier University, P.O. Box 5000,
Antigonish, Nova Scotia, Canada B2G 2W5
;
_publ_contact_author_email     'maquino@stfx.ca'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '++902-867-5336'
_publ_section_title
;
1,3-Bis(2,4,6-trimethylphenyl)imidazolium perchlorate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wang, Ruiyao' .
;
Department of Chemistry
Xi'an Jiaotong-Liverpool University
111 Renai Road, Suzhou
Jiangsu, 215123
People's Republic of China
;
    'Aquino, Manuel A.S.' .
;
Department of Chemistry, St. Francis Xavier University, P.O. Box 5000,
Antigonish, Nova Scotia, Canada B2G 2W5
;
_publ_section_synopsis
;
The molecular and crystal structure of a perchlorate salt of the
1,3-bis(2,4,6-trimethylphenyl)imidazolium cation is reported.
;
_chemical_name_systematic
;
1,3-Bis(2,4,6-trimethylphenyl)imidazolium perchlorate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H25 N2 +, Cl O4 -'
_chemical_formula_sum     'C21 H25 Cl N2 O4'
_chemical_formula_iupac     'C21 H25 N2 +, Cl O4 -'
_chemical_formula_weight     404.88
_chemical_melting_point     ?
_chemical_absolute_configuration     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P c'
_space_group_name_Hall     'P -2yc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    'x, -y, z+1/2'
_cell_length_a     8.4771(2)
_cell_length_b     16.0726(4)
_cell_length_c     15.7922(3)
_cell_angle_alpha     90
_cell_angle_beta     103.9580(10)
_cell_angle_gamma     90
_cell_volume     2088.14(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3592
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     26.22
_cell_measurement_temperature     180(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.250
_exptl_crystal_size_mid     0.200
_exptl_crystal_size_min     0.080
_exptl_crystal_density_diffrn     1.288
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     856
_exptl_absorpt_coefficient_mu     0.212
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2010)
;
_exptl_absorpt_correction_T_min     0.9490
_exptl_absorpt_correction_T_max     0.9833
_diffrn_ambient_temperature     180(2)
_diffrn_source     'fine-focus sealed tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9700
_diffrn_reflns_av_R_equivalents     0.0248
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_theta_min     1.836
_diffrn_reflns_theta_max     25.990
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     19
_refine_special_details
;
 Refined as a 2-component inversion twin.
 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     5877
_reflns_number_gt     5049
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0473
_refine_ls_R_factor_gt     0.0378
_refine_ls_wR_factor_gt     0.0918
_refine_ls_wR_factor_ref     0.0987
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.037
_refine_ls_number_reflns     5877
_refine_ls_number_parameters     518
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0521P)²+0.1933P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.179
_refine_diff_density_min     -0.287
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack     0.11(7)
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, 2010)
;
_computing_cell_refinement
;
SAINT (Bruker, 2010)
;
_computing_data_reduction
;
SAINT (Bruker, 2010)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.2216(4) 0.56851(17) -0.06414(17) 0.0294(6) Uani d 1 . .
    N N2 0.1903(3) 0.57959(17) 0.06729(17) 0.0284(6) Uani d 1 . .
    N N3 0.6168(4) 0.06465(17) -0.06288(17) 0.0296(7) Uani d 1 . .
    N N4 0.5868(3) 0.07431(17) 0.06929(17) 0.0279(6) Uani d 1 . .
    C C1 0.2506(4) 0.6165(2) 0.0063(2) 0.0274(7) Uani d 1 . .
    H H1A 0.305234 0.668566 0.012313 0.033 Uiso calc 1 . .
    C C2 0.1378(5) 0.4991(2) -0.0484(2) 0.0383(9) Uani d 1 . .
    H H2A 0.100289 0.454850 -0.087960 0.046 Uiso calc 1 . .
    C C3 0.1191(5) 0.5058(2) 0.0337(2) 0.0361(9) Uani d 1 . .
    H H3A 0.066664 0.466832 0.062939 0.043 Uiso calc 1 . .
    C C4 0.2781(4) 0.5859(2) -0.1422(2) 0.0281(8) Uani d 1 . .
    C C5 0.1696(5) 0.6240(2) -0.2123(2) 0.0336(8) Uani d 1 . .
    C C6 0.2302(5) 0.6416(2) -0.2856(2) 0.0404(10) Uani d 1 . .
    H H6A 0.160705 0.667849 -0.334511 0.048 Uiso calc 1 . .
    C C7 0.3861(5) 0.6223(2) -0.2892(2) 0.0385(9) Uani d 1 . .
    C C8 0.4882(5) 0.5830(2) -0.2179(2) 0.0390(9) Uani d 1 . .
    H H8A 0.596135 0.569337 -0.220130 0.047 Uiso calc 1 . .
    C C9 0.4347(5) 0.5634(2) -0.1430(2) 0.0333(8) Uani d 1 . .
    C C10 -0.0005(5) 0.6463(3) -0.2089(3) 0.0541(12) Uani d 1 . .
    H H10A 0.002536 0.681936 -0.158141 0.081 Uiso calc 1 . .
    H H10B -0.061391 0.595436 -0.203965 0.081 Uiso calc 1 . .
    H H10C -0.053771 0.676104 -0.262248 0.081 Uiso calc 1 . .
    C C11 0.4493(6) 0.6432(3) -0.3678(3) 0.0563(12) Uani d 1 . .
    H H11A 0.379572 0.685500 -0.402777 0.084 Uiso calc 1 . .
    H H11B 0.449207 0.592976 -0.403026 0.084 Uiso calc 1 . .
    H H11C 0.560481 0.664637 -0.348748 0.084 Uiso calc 1 . .
    C C12 0.5465(5) 0.5209(3) -0.0664(2) 0.0483(11) Uani d 1 . .
    H H12A 0.563672 0.557230 -0.015094 0.073 Uiso calc 1 . .
    H H12B 0.651022 0.509474 -0.080179 0.073 Uiso calc 1 . .
    H H12C 0.497272 0.468529 -0.054071 0.073 Uiso calc 1 . .
    C C13 0.1951(4) 0.6141(2) 0.1526(2) 0.0291(8) Uani d 1 . .
    C C14 0.3458(4) 0.6305(2) 0.2093(2) 0.0317(8) Uani d 1 . .
    C C15 0.3442(5) 0.6652(2) 0.2898(2) 0.0357(9) Uani d 1 . .
    H H15A 0.445012 0.677350 0.329421 0.043 Uiso calc 1 . .
    C C16 0.2030(5) 0.6825(2) 0.3145(2) 0.0330(8) Uani d 1 . .
    C C17 0.0552(5) 0.6646(2) 0.2568(2) 0.0353(8) Uani d 1 . .
    H H17A -0.043016 0.675867 0.273555 0.042 Uiso calc 1 . .
    C C18 0.0480(4) 0.6303(2) 0.1747(2) 0.0321(8) Uani d 1 . .
    C C19 0.5043(5) 0.6155(3) 0.1858(3) 0.0432(10) Uani d 1 . .
    H H19A 0.592296 0.614705 0.239025 0.065 Uiso calc 1 . .
    H H19B 0.523974 0.660089 0.147300 0.065 Uiso calc 1 . .
    H H19C 0.500343 0.561912 0.155792 0.065 Uiso calc 1 . .
    C C20 0.2073(5) 0.7232(2) 0.4015(2) 0.0435(10) Uani d 1 . .
    H H20A 0.317745 0.719905 0.438848 0.065 Uiso calc 1 . .
    H H20B 0.131934 0.694377 0.429776 0.065 Uiso calc 1 . .
    H H20C 0.175135 0.781692 0.392175 0.065 Uiso calc 1 . .
    C C21 -0.1132(5) 0.6144(3) 0.1114(3) 0.0450(10) Uani d 1 . .
    H H21A -0.198908 0.644818 0.130297 0.067 Uiso calc 1 . .
    H H21B -0.137225 0.554651 0.109730 0.067 Uiso calc 1 . .
    H H21C -0.108348 0.633255 0.053112 0.067 Uiso calc 1 . .
    C C22 0.6483(4) 0.1107(2) 0.0089(2) 0.0290(8) Uani d 1 . .
    H H22A 0.705933 0.161930 0.015982 0.035 Uiso calc 1 . .
    C C23 0.5310(5) -0.0048(2) -0.0470(2) 0.0381(9) Uani d 1 . .
    H H23A 0.492428 -0.048828 -0.086827 0.046 Uiso calc 1 . .
    C C24 0.5125(5) 0.0015(2) 0.0343(2) 0.0382(9) Uani d 1 . .
    H H24A 0.458141 -0.037154 0.062926 0.046 Uiso calc 1 . .
    C C25 0.6691(4) 0.0848(2) -0.1410(2) 0.0299(8) Uani d 1 . .
    C C26 0.5517(5) 0.1085(2) -0.2152(2) 0.0353(9) Uani d 1 . .
    C C27 0.6090(5) 0.1336(2) -0.2872(2) 0.0417(10) Uani d 1 . .
    H H27A 0.533204 0.153149 -0.337817 0.050 Uiso calc 1 . .
    C C28 0.7706(6) 0.1309(2) -0.2873(2) 0.0439(10) Uani d 1 . .
    C C29 0.8819(5) 0.1048(3) -0.2122(2) 0.0413(10) Uani d 1 . .
    H H29A 0.994130 0.102928 -0.211641 0.050 Uiso calc 1 . .
    C C30 0.8325(5) 0.0815(2) -0.1379(2) 0.0344(9) Uani d 1 . .
    C C31 0.3741(5) 0.1083(3) -0.2191(3) 0.0530(12) Uani d 1 . .
    H H31A 0.316293 0.140696 -0.269655 0.079 Uiso calc 1 . .
    H H31B 0.355442 0.132997 -0.165633 0.079 Uiso calc 1 . .
    H H31C 0.333752 0.050876 -0.224619 0.079 Uiso calc 1 . .
    C C32 0.8276(7) 0.1557(3) -0.3665(3) 0.0636(14) Uani d 1 . .
    H H32A 0.761409 0.202142 -0.395873 0.095 Uiso calc 1 . .
    H H32B 0.816930 0.108347 -0.406574 0.095 Uiso calc 1 . .
    H H32C 0.941792 0.172928 -0.348958 0.095 Uiso calc 1 . .
    C C33 0.9582(5) 0.0541(3) -0.0571(2) 0.0501(11) Uani d 1 . .
    H H33A 0.918355 0.004857 -0.032095 0.075 Uiso calc 1 . .
    H H33B 0.977447 0.099179 -0.014142 0.075 Uiso calc 1 . .
    H H33C 1.060010 0.040410 -0.073036 0.075 Uiso calc 1 . .
    C C34 0.5987(4) 0.1071(2) 0.1559(2) 0.0281(8) Uani d 1 . .
    C C35 0.7530(4) 0.1161(2) 0.2124(2) 0.0292(8) Uani d 1 . .
    C C36 0.7620(5) 0.1519(2) 0.2932(2) 0.0339(9) Uani d 1 . .
    H H36A 0.865316 0.158801 0.332486 0.041 Uiso calc 1 . .
    C C37 0.6224(5) 0.1781(2) 0.3183(2) 0.0338(8) Uani d 1 . .
    C C38 0.4722(5) 0.1654(2) 0.2613(2) 0.0358(9) Uani d 1 . .
    H H38A 0.376804 0.180914 0.278999 0.043 Uiso calc 1 . .
    C C39 0.4567(4) 0.1307(2) 0.1789(2) 0.0311(8) Uani d 1 . .
    C C40 0.9067(4) 0.0915(2) 0.1869(2) 0.0384(9) Uani d 1 . .
    H H40A 0.995085 0.085272 0.239428 0.058 Uiso calc 1 . .
    H H40B 0.935438 0.134556 0.149317 0.058 Uiso calc 1 . .
    H H40C 0.889510 0.038503 0.155199 0.058 Uiso calc 1 . .
    C C41 0.6383(6) 0.2226(3) 0.4039(2) 0.0499(11) Uani d 1 . .
    H H41A 0.552190 0.203848 0.431176 0.075 Uiso calc 1 . .
    H H41B 0.628567 0.282686 0.393653 0.075 Uiso calc 1 . .
    H H41C 0.744623 0.210108 0.442704 0.075 Uiso calc 1 . .
    C C42 0.2906(5) 0.1227(3) 0.1162(3) 0.0433(10) Uani d 1 . .
    H H42A 0.299361 0.135682 0.056868 0.065 Uiso calc 1 . .
    H H42B 0.214734 0.161535 0.133280 0.065 Uiso calc 1 . .
    H H42C 0.250677 0.065660 0.117998 0.065 Uiso calc 1 . .
    Cl Cl1 0.19602(10) 0.84117(6) -0.00581(6) 0.0367(2) Uani d 1 . .
    Cl Cl2 0.80684(10) 0.33141(6) 0.00185(6) 0.0359(2) Uani d 1 . .
    O O1 0.3521(3) 0.80080(18) 0.02427(18) 0.0481(7) Uani d 1 . .
    O O2 0.0698(3) 0.78046(16) -0.01380(19) 0.0495(7) Uani d 1 . .
    O O3 0.1824(4) 0.90408(17) 0.05591(18) 0.0492(7) Uani d 1 . .
    O O4 0.1895(4) 0.8787(2) -0.08888(19) 0.0627(9) Uani d 1 . .
    O O5 0.6417(3) 0.30266(17) -0.02108(17) 0.0425(7) Uani d 1 . .
    O O6 0.9118(3) 0.26184(17) 0.03387(19) 0.0513(8) Uani d 1 . .
    O O7 0.8257(4) 0.39378(17) 0.06874(18) 0.0498(8) Uani d 1 . .
    O O8 0.8495(4) 0.36686(18) -0.07326(19) 0.0536(8) Uani d 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
    N1 C1 . 1.327(4) ?
    N1 C2 . 1.376(4) ?
    N1 C4 . 1.453(4) ?
    N2 C1 . 1.333(4) ?
    N2 C3 . 1.378(4) ?
    N2 C13 . 1.449(4) ?
    N3 C22 . 1.326(4) ?
    N3 C23 . 1.388(4) ?
    N3 C25 . 1.445(4) ?
    N4 C22 . 1.328(4) ?
    N4 C24 . 1.380(4) ?
    N4 C34 . 1.447(4) ?
    C1 H1A . 0.9500 ?
    C2 C3 . 1.347(5) ?
    C2 H2A . 0.9500 ?
    C3 H3A . 0.9500 ?
    C4 C9 . 1.379(5) ?
    C4 C5 . 1.399(5) ?
    C5 C6 . 1.404(5) ?
    C5 C10 . 1.499(6) ?
    C6 C7 . 1.372(6) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.395(5) ?
    C7 C11 . 1.503(5) ?
    C8 C9 . 1.400(5) ?
    C8 H8A . 0.9500 ?
    C9 C12 . 1.509(5) ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 C14 . 1.396(5) ?
    C13 C18 . 1.398(5) ?
    C14 C15 . 1.392(5) ?
    C14 C19 . 1.497(5) ?
    C15 C16 . 1.374(5) ?
    C15 H15A . 0.9500 ?
    C16 C17 . 1.390(5) ?
    C16 C20 . 1.514(5) ?
    C17 C18 . 1.396(5) ?
    C17 H17A . 0.9500 ?
    C18 C21 . 1.508(5) ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 0.9800 ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    C22 H22A . 0.9500 ?
    C23 C24 . 1.335(5) ?
    C23 H23A . 0.9500 ?
    C24 H24A . 0.9500 ?
    C25 C30 . 1.375(5) ?
    C25 C26 . 1.394(5) ?
    C26 C27 . 1.400(5) ?
    C26 C31 . 1.492(6) ?
    C27 C28 . 1.371(6) ?
    C27 H27A . 0.9500 ?
    C28 C29 . 1.391(6) ?
    C28 C32 . 1.500(6) ?
    C29 C30 . 1.389(5) ?
    C29 H29A . 0.9500 ?
    C30 C33 . 1.516(5) ?
    C31 H31A . 0.9800 ?
    C31 H31B . 0.9800 ?
    C31 H31C . 0.9800 ?
    C32 H32A . 0.9800 ?
    C32 H32B . 0.9800 ?
    C32 H32C . 0.9800 ?
    C33 H33A . 0.9800 ?
    C33 H33B . 0.9800 ?
    C33 H33C . 0.9800 ?
    C34 C39 . 1.391(5) ?
    C34 C35 . 1.402(5) ?
    C35 C36 . 1.384(5) ?
    C35 C40 . 1.507(5) ?
    C36 C37 . 1.400(6) ?
    C36 H36A . 0.9500 ?
    C37 C38 . 1.386(5) ?
    C37 C41 . 1.507(5) ?
    C38 C39 . 1.393(5) ?
    C38 H38A . 0.9500 ?
    C39 C42 . 1.518(5) ?
    C40 H40A . 0.9800 ?
    C40 H40B . 0.9800 ?
    C40 H40C . 0.9800 ?
    C41 H41A . 0.9800 ?
    C41 H41B . 0.9800 ?
    C41 H41C . 0.9800 ?
    C42 H42A . 0.9800 ?
    C42 H42B . 0.9800 ?
    C42 H42C . 0.9800 ?
    Cl1 O3 . 1.428(3) ?
    Cl1 O2 . 1.431(3) ?
    Cl1 O4 . 1.433(3) ?
    Cl1 O1 . 1.447(3) ?
    Cl2 O5 . 1.435(3) ?
    Cl2 O7 . 1.437(3) ?
    Cl2 O8 . 1.439(3) ?
    Cl2 O6 . 1.443(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
    C1 N1 C2 . . 108.6(3) ?
    C1 N1 C4 . . 124.6(3) ?
    C2 N1 C4 . . 126.8(3) ?
    C1 N2 C3 . . 108.3(3) ?
    C1 N2 C13 . . 124.9(3) ?
    C3 N2 C13 . . 126.8(3) ?
    C22 N3 C23 . . 107.5(3) ?
    C22 N3 C25 . . 124.4(3) ?
    C23 N3 C25 . . 128.0(3) ?
    C22 N4 C24 . . 107.8(3) ?
    C22 N4 C34 . . 124.7(3) ?
    C24 N4 C34 . . 127.5(3) ?
    N1 C1 N2 . . 108.7(3) ?
    N1 C1 H1A . . 125.6 ?
    N2 C1 H1A . . 125.6 ?
    C3 C2 N1 . . 107.2(3) ?
    C3 C2 H2A . . 126.4 ?
    N1 C2 H2A . . 126.4 ?
    C2 C3 N2 . . 107.3(3) ?
    C2 C3 H3A . . 126.4 ?
    N2 C3 H3A . . 126.4 ?
    C9 C4 C5 . . 123.9(3) ?
    C9 C4 N1 . . 118.2(3) ?
    C5 C4 N1 . . 117.8(3) ?
    C4 C5 C6 . . 116.0(4) ?
    C4 C5 C10 . . 122.1(3) ?
    C6 C5 C10 . . 121.9(4) ?
    C7 C6 C5 . . 122.5(4) ?
    C7 C6 H6A . . 118.8 ?
    C5 C6 H6A . . 118.8 ?
    C6 C7 C8 . . 119.0(4) ?
    C6 C7 C11 . . 121.5(4) ?
    C8 C7 C11 . . 119.5(4) ?
    C7 C8 C9 . . 121.3(4) ?
    C7 C8 H8A . . 119.4 ?
    C9 C8 H8A . . 119.4 ?
    C4 C9 C8 . . 117.2(3) ?
    C4 C9 C12 . . 122.0(3) ?
    C8 C9 C12 . . 120.7(4) ?
    C5 C10 H10A . . 109.5 ?
    C5 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C5 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C7 C11 H11A . . 109.5 ?
    C7 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C7 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C9 C12 H12A . . 109.5 ?
    C9 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C9 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C14 C13 C18 . . 122.5(3) ?
    C14 C13 N2 . . 119.0(3) ?
    C18 C13 N2 . . 118.5(3) ?
    C15 C14 C13 . . 116.9(3) ?
    C15 C14 C19 . . 119.9(3) ?
    C13 C14 C19 . . 123.2(3) ?
    C16 C15 C14 . . 122.8(3) ?
    C16 C15 H15A . . 118.6 ?
    C14 C15 H15A . . 118.6 ?
    C15 C16 C17 . . 118.7(3) ?
    C15 C16 C20 . . 120.9(3) ?
    C17 C16 C20 . . 120.4(4) ?
    C16 C17 C18 . . 121.4(3) ?
    C16 C17 H17A . . 119.3 ?
    C18 C17 H17A . . 119.3 ?
    C17 C18 C13 . . 117.6(3) ?
    C17 C18 C21 . . 120.8(3) ?
    C13 C18 C21 . . 121.6(3) ?
    C14 C19 H19A . . 109.5 ?
    C14 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C14 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C16 C20 H20A . . 109.5 ?
    C16 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C16 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    C18 C21 H21A . . 109.5 ?
    C18 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C18 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    N3 C22 N4 . . 109.6(3) ?
    N3 C22 H22A . . 125.2 ?
    N4 C22 H22A . . 125.2 ?
    C24 C23 N3 . . 107.5(3) ?
    C24 C23 H23A . . 126.3 ?
    N3 C23 H23A . . 126.3 ?
    C23 C24 N4 . . 107.5(3) ?
    C23 C24 H24A . . 126.2 ?
    N4 C24 H24A . . 126.2 ?
    C30 C25 C26 . . 123.3(3) ?
    C30 C25 N3 . . 118.3(3) ?
    C26 C25 N3 . . 118.3(3) ?
    C25 C26 C27 . . 116.4(4) ?
    C25 C26 C31 . . 122.9(4) ?
    C27 C26 C31 . . 120.8(3) ?
    C28 C27 C26 . . 122.3(3) ?
    C28 C27 H27A . . 118.8 ?
    C26 C27 H27A . . 118.8 ?
    C27 C28 C29 . . 118.7(4) ?
    C27 C28 C32 . . 121.1(4) ?
    C29 C28 C32 . . 120.2(4) ?
    C30 C29 C28 . . 121.4(4) ?
    C30 C29 H29A . . 119.3 ?
    C28 C29 H29A . . 119.3 ?
    C25 C30 C29 . . 117.7(3) ?
    C25 C30 C33 . . 122.6(4) ?
    C29 C30 C33 . . 119.7(4) ?
    C26 C31 H31A . . 109.5 ?
    C26 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    C26 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
    C28 C32 H32A . . 109.5 ?
    C28 C32 H32B . . 109.5 ?
    H32A C32 H32B . . 109.5 ?
    C28 C32 H32C . . 109.5 ?
    H32A C32 H32C . . 109.5 ?
    H32B C32 H32C . . 109.5 ?
    C30 C33 H33A . . 109.5 ?
    C30 C33 H33B . . 109.5 ?
    H33A C33 H33B . . 109.5 ?
    C30 C33 H33C . . 109.5 ?
    H33A C33 H33C . . 109.5 ?
    H33B C33 H33C . . 109.5 ?
    C39 C34 C35 . . 122.7(3) ?
    C39 C34 N4 . . 118.6(3) ?
    C35 C34 N4 . . 118.8(3) ?
    C36 C35 C34 . . 117.7(3) ?
    C36 C35 C40 . . 119.8(3) ?
    C34 C35 C40 . . 122.5(3) ?
    C35 C36 C37 . . 121.6(3) ?
    C35 C36 H36A . . 119.2 ?
    C37 C36 H36A . . 119.2 ?
    C38 C37 C36 . . 118.6(3) ?
    C38 C37 C41 . . 121.4(4) ?
    C36 C37 C41 . . 119.9(3) ?
    C37 C38 C39 . . 122.0(4) ?
    C37 C38 H38A . . 119.0 ?
    C39 C38 H38A . . 119.0 ?
    C34 C39 C38 . . 117.4(3) ?
    C34 C39 C42 . . 122.1(3) ?
    C38 C39 C42 . . 120.5(3) ?
    C35 C40 H40A . . 109.5 ?
    C35 C40 H40B . . 109.5 ?
    H40A C40 H40B . . 109.5 ?
    C35 C40 H40C . . 109.5 ?
    H40A C40 H40C . . 109.5 ?
    H40B C40 H40C . . 109.5 ?
    C37 C41 H41A . . 109.5 ?
    C37 C41 H41B . . 109.5 ?
    H41A C41 H41B . . 109.5 ?
    C37 C41 H41C . . 109.5 ?
    H41A C41 H41C . . 109.5 ?
    H41B C41 H41C . . 109.5 ?
    C39 C42 H42A . . 109.5 ?
    C39 C42 H42B . . 109.5 ?
    H42A C42 H42B . . 109.5 ?
    C39 C42 H42C . . 109.5 ?
    H42A C42 H42C . . 109.5 ?
    H42B C42 H42C . . 109.5 ?
    O3 Cl1 O2 . . 111.17(19) ?
    O3 Cl1 O4 . . 109.58(19) ?
    O2 Cl1 O4 . . 110.09(19) ?
    O3 Cl1 O1 . . 108.15(17) ?
    O2 Cl1 O1 . . 109.15(17) ?
    O4 Cl1 O1 . . 108.6(2) ?
    O5 Cl2 O7 . . 109.80(19) ?
    O5 Cl2 O8 . . 110.09(18) ?
    O7 Cl2 O8 . . 108.92(18) ?
    O5 Cl2 O6 . . 108.70(16) ?
    O7 Cl2 O6 . . 109.47(18) ?
    O8 Cl2 O6 . . 109.85(19) ?
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
    C2 N1 C1 N2 . . . . 0.9(4) ?
    C4 N1 C1 N2 . . . . -176.1(3) ?
    C3 N2 C1 N1 . . . . -0.6(4) ?
    C13 N2 C1 N1 . . . . -178.5(3) ?
    C1 N1 C2 C3 . . . . -0.9(4) ?
    C4 N1 C2 C3 . . . . 176.0(3) ?
    N1 C2 C3 N2 . . . . 0.5(4) ?
    C1 N2 C3 C2 . . . . 0.0(4) ?
    C13 N2 C3 C2 . . . . 177.9(3) ?
    C1 N1 C4 C9 . . . . 82.7(4) ?
    C2 N1 C4 C9 . . . . -93.7(4) ?
    C1 N1 C4 C5 . . . . -97.7(4) ?
    C2 N1 C4 C5 . . . . 85.9(4) ?
    C9 C4 C5 C6 . . . . -1.9(5) ?
    N1 C4 C5 C6 . . . . 178.5(3) ?
    C9 C4 C5 C10 . . . . 179.2(4) ?
    N1 C4 C5 C10 . . . . -0.5(5) ?
    C4 C5 C6 C7 . . . . 0.4(6) ?
    C10 C5 C6 C7 . . . . 179.3(4) ?
    C5 C6 C7 C8 . . . . 0.6(6) ?
    C5 C6 C7 C11 . . . . -178.8(4) ?
    C6 C7 C8 C9 . . . . -0.2(6) ?
    C11 C7 C8 C9 . . . . 179.2(4) ?
    C5 C4 C9 C8 . . . . 2.3(5) ?
    N1 C4 C9 C8 . . . . -178.1(3) ?
    C5 C4 C9 C12 . . . . -178.9(3) ?
    N1 C4 C9 C12 . . . . 0.8(5) ?
    C7 C8 C9 C4 . . . . -1.1(5) ?
    C7 C8 C9 C12 . . . . 180.0(3) ?
    C1 N2 C13 C14 . . . . -60.9(5) ?
    C3 N2 C13 C14 . . . . 121.6(4) ?
    C1 N2 C13 C18 . . . . 118.6(4) ?
    C3 N2 C13 C18 . . . . -58.9(5) ?
    C18 C13 C14 C15 . . . . -0.7(5) ?
    N2 C13 C14 C15 . . . . 178.8(3) ?
    C18 C13 C14 C19 . . . . -178.4(4) ?
    N2 C13 C14 C19 . . . . 1.0(5) ?
    C13 C14 C15 C16 . . . . 0.5(6) ?
    C19 C14 C15 C16 . . . . 178.3(4) ?
    C14 C15 C16 C17 . . . . 0.1(6) ?
    C14 C15 C16 C20 . . . . -177.7(3) ?
    C15 C16 C17 C18 . . . . -0.6(6) ?
    C20 C16 C17 C18 . . . . 177.2(3) ?
    C16 C17 C18 C13 . . . . 0.4(5) ?
    C16 C17 C18 C21 . . . . -177.5(3) ?
    C14 C13 C18 C17 . . . . 0.3(5) ?
    N2 C13 C18 C17 . . . . -179.2(3) ?
    C14 C13 C18 C21 . . . . 178.2(4) ?
    N2 C13 C18 C21 . . . . -1.3(5) ?
    C23 N3 C22 N4 . . . . -0.1(4) ?
    C25 N3 C22 N4 . . . . -178.6(3) ?
    C24 N4 C22 N3 . . . . 0.0(4) ?
    C34 N4 C22 N3 . . . . 179.8(3) ?
    C22 N3 C23 C24 . . . . 0.2(4) ?
    C25 N3 C23 C24 . . . . 178.6(3) ?
    N3 C23 C24 N4 . . . . -0.2(4) ?
    C22 N4 C24 C23 . . . . 0.1(4) ?
    C34 N4 C24 C23 . . . . -179.6(3) ?
    C22 N3 C25 C30 . . . . 68.2(5) ?
    C23 N3 C25 C30 . . . . -110.0(4) ?
    C22 N3 C25 C26 . . . . -110.3(4) ?
    C23 N3 C25 C26 . . . . 71.5(5) ?
    C30 C25 C26 C27 . . . . -3.1(5) ?
    N3 C25 C26 C27 . . . . 175.3(3) ?
    C30 C25 C26 C31 . . . . 177.2(4) ?
    N3 C25 C26 C31 . . . . -4.4(5) ?
    C25 C26 C27 C28 . . . . 3.4(6) ?
    C31 C26 C27 C28 . . . . -176.9(4) ?
    C26 C27 C28 C29 . . . . -2.0(6) ?
    C26 C27 C28 C32 . . . . 178.1(4) ?
    C27 C28 C29 C30 . . . . 0.1(6) ?
    C32 C28 C29 C30 . . . . -180.0(4) ?
    C26 C25 C30 C29 . . . . 1.4(5) ?
    N3 C25 C30 C29 . . . . -177.0(3) ?
    C26 C25 C30 C33 . . . . -178.9(4) ?
    N3 C25 C30 C33 . . . . 2.7(5) ?
    C28 C29 C30 C25 . . . . 0.2(6) ?
    C28 C29 C30 C33 . . . . -179.5(4) ?
    C22 N4 C34 C39 . . . . 115.3(4) ?
    C24 N4 C34 C39 . . . . -65.0(5) ?
    C22 N4 C34 C35 . . . . -62.8(5) ?
    C24 N4 C34 C35 . . . . 117.0(4) ?
    C39 C34 C35 C36 . . . . -1.5(5) ?
    N4 C34 C35 C36 . . . . 176.5(3) ?
    C39 C34 C35 C40 . . . . -179.2(3) ?
    N4 C34 C35 C40 . . . . -1.2(5) ?
    C34 C35 C36 C37 . . . . 0.2(5) ?
    C40 C35 C36 C37 . . . . 177.9(3) ?
    C35 C36 C37 C38 . . . . 1.8(5) ?
    C35 C36 C37 C41 . . . . -175.4(3) ?
    C36 C37 C38 C39 . . . . -2.7(5) ?
    C41 C37 C38 C39 . . . . 174.5(3) ?
    C35 C34 C39 C38 . . . . 0.7(5) ?
    N4 C34 C39 C38 . . . . -177.3(3) ?
    C35 C34 C39 C42 . . . . 178.4(3) ?
    N4 C34 C39 C42 . . . . 0.4(5) ?
    C37 C38 C39 C34 . . . . 1.4(5) ?
    C37 C38 C39 C42 . . . . -176.3(3) ?
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
    C1 H1A Cl1 . 0.95 2.92 3.639(3) 133.8 no
    C1 H1A O1 . 0.95 2.16 3.078(4) 161.7 yes
    C2 H2A O8 1_455 0.95 2.61 3.191(5) 119.9 yes
    C3 H3A O7 1_455 0.95 2.38 3.225(5) 148.4 yes
    C22 H22A Cl2 . 0.95 2.88 3.804(4) 164.6 no
    C22 H22A O5 . 0.95 2.37 3.119(4) 135.9 yes
    C22 H22A O6 . 0.95 2.34 3.259(4) 163.2 yes
    C24 H24A Cl1 1_545 0.95 2.96 3.663(4) 131.6 no
    C24 H24A O3 1_545 0.95 2.50 3.295(5) 141.4 yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.949
_shelx_estimated_absorpt_T_max     0.983
