##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# 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     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.3
_journal_date_recd_electronic     2012-07-13
_journal_date_accepted     2012-07-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      8
_journal_page_first     o2538
_journal_page_last     o2538
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812032540
_journal_coeditor_code     ZJ2089
_publ_contact_author_name     'Fronczek, Frank R.'
_publ_contact_author_address
;
Department of Chemistry
Louisiana State University
Baton Rouge
LA 70803-1804
USA
;
_publ_contact_author_email     ffroncz@lsu.edu
_publ_contact_author_fax     '225-578-3458'
_publ_contact_author_phone     '225-578-8270'
_publ_section_title
;\
1,2,3,4,5,6,7,8,13,13,14,14-Dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-1,4:5,\
8-dimethanotriphenylene at 90 K
;
_publ_section_title_footnote
;
 CAS 147730-93-6.
;
loop_
    _publ_author_name
    _publ_author_address
    'Jenkins, Brandon W.'
;
Department of Chemistry
Louisiana State University
Baton Rouge
LA 70803-1804
USA
;
    'Fronczek, Frank R.'
;
Department of Chemistry
Louisiana State University
Baton Rouge
LA 70803-1804
USA
;
    'Watkins, Steven F.'
;
Department of Chemistry
Louisiana State University
Baton Rouge
LA 70803-1804
USA
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
1,2,3,4,5,6,7,8,13,13,14,14-Dodecachloro-1,4,4a,4b,5,8,8a,12b-
octahydro-1,4:5,8-dimethanotriphenylene
;
_chemical_formula_moiety     'C20 H8 Cl12'
_chemical_formula_sum     'C20 H8 Cl12'
_chemical_formula_iupac     'C20 H8 Cl12'
_chemical_formula_weight     673.66
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.64340(10)
_cell_length_b     15.4287(2)
_cell_length_c     16.4161(2)
_cell_angle_alpha     92.1948(6)
_cell_angle_beta     98.2331(7)
_cell_angle_gamma     91.3097(6)
_cell_volume     2414.53(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     27797
_cell_measurement_theta_min     2.546
_cell_measurement_theta_max     40.25
_cell_measurement_temperature     90.0(5)
_cell_measurement_pressure     101.3
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.853
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1328
_exptl_absorpt_coefficient_mu     1.387
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.6069
_exptl_absorpt_correction_T_max     0.819
_diffrn_ambient_temperature     90.0(5)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'horizonally mounted graphite crystal'
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_device     '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method     'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     111692
_diffrn_reflns_av_R_equivalents     0.0263
_diffrn_reflns_theta_min     2.63
_diffrn_reflns_theta_max     40.28
_diffrn_reflns_theta_full     25
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -28
_diffrn_reflns_limit_k_max     28
_diffrn_reflns_limit_l_min     -29
_diffrn_reflns_limit_l_max     29
_reflns_number_total     30125
_reflns_number_gt     24699
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt     0.0322
_refine_ls_wR_factor_ref     0.0858
_refine_ls_goodness_of_fit_ref     1.029
_refine_ls_restrained_S_all     1.029
_refine_ls_number_reflns     30125
_refine_ls_number_parameters     578
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0362P)²+1.2577P] 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     0.002
_refine_diff_density_max     0.872
_refine_diff_density_min     -0.633
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0013(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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 0 '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     'COLLECT (Nonius, 2000)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    C C1 0.78302(10) 0.24744(6) 0.36584(6) 0.01060(13) Uani d . 1 . .
    H H1 0.718 0.2785 0.3984 0.013 Uiso calc R 1 . .
    C C2 0.76826(10) 0.15090(6) 0.37568(6) 0.01118(14) Uani d . 1 . .
    C C3 0.77164(12) 0.12163(7) 0.45581(6) 0.01484(16) Uani d . 1 . .
    H H3 0.7646 0.1622 0.4999 0.018 Uiso calc R 1 . .
    C C4 0.78510(13) 0.03398(7) 0.47153(7) 0.01839(18) Uani d . 1 . .
    H H4 0.7853 0.0148 0.5258 0.022 Uiso calc R 1 . .
    C C5 0.79834(13) -0.02536(7) 0.40736(7) 0.01770(18) Uani d . 1 . .
    H H5 0.8149 -0.0845 0.4183 0.021 Uiso calc R 1 . .
    C C6 0.78719(12) 0.00244(7) 0.32715(7) 0.01483(16) Uani d . 1 . .
    H H6 0.7938 -0.0386 0.2833 0.018 Uiso calc R 1 . .
    C C7 0.76641(10) 0.08995(6) 0.30980(6) 0.01141(14) Uani d . 1 . .
    C C8 0.72700(10) 0.11372(6) 0.22086(6) 0.01102(13) Uani d . 1 . .
    H H8 0.7957 0.0893 0.1866 0.013 Uiso calc R 1 . .
    C C9 0.70962(10) 0.21274(6) 0.20593(6) 0.01055(13) Uani d . 1 . .
    H H9 0.7587 0.2264 0.1581 0.013 Uiso calc R 1 . .
    C C10 0.76252(10) 0.27912(6) 0.27577(6) 0.01032(13) Uani d . 1 . .
    H H10 0.6952 0.3276 0.273 0.012 Uiso calc R 1 . .
    C C11 0.91010(10) 0.31842(6) 0.26664(6) 0.01082(13) Uani d . 1 . .
    C C12 0.95297(10) 0.36467(6) 0.35265(6) 0.01182(14) Uani d . 1 . .
    C C13 0.94026(10) 0.27907(6) 0.39788(6) 0.01102(13) Uani d . 1 . .
    C C14 1.03221(10) 0.22190(6) 0.35207(6) 0.01196(14) Uani d . 1 . .
    C C15 1.01323(10) 0.24454(7) 0.27332(6) 0.01183(14) Uani d . 1 . .
    C C16 0.54883(10) 0.21886(6) 0.17658(6) 0.01145(14) Uani d . 1 . .
    C C17 0.52148(10) 0.13722(6) 0.11775(6) 0.01270(14) Uani d . 1 . .
    C C18 0.57301(10) 0.07562(6) 0.18742(6) 0.01136(14) Uani d . 1 . .
    C C19 0.48189(10) 0.10455(6) 0.25116(6) 0.01187(14) Uani d . 1 . .
    C C20 0.47091(10) 0.19063(6) 0.24619(6) 0.01197(14) Uani d . 1 . .
    Cl Cl1 0.83666(3) 0.444688(16) 0.378408(16) 0.01515(4) Uani d . 1 . .
    Cl Cl2 1.12467(3) 0.411451(17) 0.367166(16) 0.01537(4) Uani d . 1 . .
    Cl Cl3 0.98690(3) 0.288372(18) 0.504965(14) 0.01546(4) Uani d . 1 . .
    Cl Cl4 1.12522(3) 0.138821(18) 0.394002(17) 0.01819(5) Uani d . 1 . .
    Cl Cl5 1.07638(3) 0.195595(19) 0.192404(16) 0.01775(4) Uani d . 1 . .
    Cl Cl6 0.91267(3) 0.383648(17) 0.181692(15) 0.01553(4) Uani d . 1 . .
    Cl Cl7 0.62374(3) 0.132935(18) 0.036646(15) 0.01693(4) Uani d . 1 . .
    Cl Cl8 0.34348(3) 0.119848(18) 0.074104(16) 0.01669(4) Uani d . 1 . .
    Cl Cl9 0.56086(3) -0.034447(16) 0.156692(16) 0.01555(4) Uani d . 1 . .
    Cl Cl10 0.42601(3) 0.039085(17) 0.321116(17) 0.01683(4) Uani d . 1 . .
    Cl Cl11 0.40182(3) 0.259640(17) 0.311679(18) 0.01724(4) Uani d . 1 . .
    Cl Cl12 0.49903(3) 0.317864(16) 0.134127(17) 0.01638(4) Uani d . 1 . .
    C C21 0.70185(10) 0.39226(6) 0.72349(6) 0.01099(13) Uani d . 1 . .
    H H21 0.7764 0.4224 0.6977 0.013 Uiso calc R 1 . .
    C C22 0.72147(10) 0.41473(6) 0.81506(6) 0.01236(14) Uani d . 1 . .
    C C23 0.73181(12) 0.50254(7) 0.84174(7) 0.01735(18) Uani d . 1 . .
    H H23 0.7441 0.5457 0.8035 0.021 Uiso calc R 1 . .
    C C24 0.72439(14) 0.52707(8) 0.92324(8) 0.0220(2) Uani d . 1 . .
    H H24 0.7347 0.5865 0.9408 0.026 Uiso calc R 1 . .
    C C25 0.70191(15) 0.46452(9) 0.97910(7) 0.0227(2) Uani d . 1 . .
    H H25 0.6883 0.4814 1.0336 0.027 Uiso calc R 1 . .
    C C26 0.69956(13) 0.37723(8) 0.95468(7) 0.01833(18) Uani d . 1 . .
    H H26 0.6872 0.3344 0.9933 0.022 Uiso calc R 1 . .
    C C27 0.71524(11) 0.35144(7) 0.87372(6) 0.01303(15) Uani d . 1 . .
    C C28 0.74356(10) 0.25743(6) 0.85610(6) 0.01152(14) Uani d . 1 . .
    H H28 0.6781 0.2197 0.8822 0.014 Uiso calc R 1 . .
    C C29 0.73930(10) 0.22747(6) 0.76363(6) 0.01075(13) Uani d . 1 . .
    H H29 0.6754 0.1751 0.7523 0.013 Uiso calc R 1 . .
    C C30 0.69489(10) 0.29315(6) 0.69746(6) 0.01106(13) Uani d . 1 . .
    H H30 0.7566 0.2851 0.6539 0.013 Uiso calc R 1 . .
    C C31 0.54023(10) 0.27880(6) 0.65463(6) 0.01190(14) Uani d . 1 . .
    C C32 0.52032(10) 0.36220(6) 0.60443(6) 0.01211(14) Uani d . 1 . .
    C C33 0.55125(10) 0.42229(6) 0.68299(6) 0.01044(13) Uani d . 1 . .
    C C34 0.44750(10) 0.38391(6) 0.73405(6) 0.01182(14) Uani d . 1 . .
    C C35 0.44278(10) 0.29802(6) 0.71796(6) 0.01284(15) Uani d . 1 . .
    C C36 0.89301(10) 0.19842(6) 0.75984(6) 0.01145(14) Uani d . 1 . .
    C C37 0.92908(10) 0.15480(6) 0.84375(6) 0.01255(14) Uani d . 1 . .
    C C38 0.90153(10) 0.23844(6) 0.89310(6) 0.01190(14) Uani d . 1 . .
    C C39 0.99247(10) 0.30344(7) 0.85577(6) 0.01231(14) Uani d . 1 . .
    C C40 0.98700(10) 0.27995(7) 0.77598(6) 0.01191(14) Uani d . 1 . .
    Cl Cl13 0.64205(3) 0.377793(19) 0.534965(15) 0.01720(4) Uani d . 1 . .
    Cl Cl14 0.34960(3) 0.370694(18) 0.549642(16) 0.01676(4) Uani d . 1 . .
    Cl Cl15 0.53663(3) 0.532852(15) 0.665173(16) 0.01426(4) Uani d . 1 . .
    Cl Cl16 0.37045(3) 0.441131(18) 0.804244(17) 0.01757(4) Uani d . 1 . .
    Cl Cl17 0.35863(3) 0.221032(19) 0.76498(2) 0.02185(5) Uani d . 1 . .
    Cl Cl18 0.50770(3) 0.180207(17) 0.597606(18) 0.01900(5) Uani d . 1 . .
    Cl Cl19 0.81665(3) 0.066381(16) 0.857572(17) 0.01663(4) Uani d . 1 . .
    Cl Cl20 1.10430(3) 0.120062(18) 0.864312(16) 0.01591(4) Uani d . 1 . .
    Cl Cl21 0.93820(3) 0.232330(19) 1.000170(15) 0.01646(4) Uani d . 1 . .
    Cl Cl22 1.06791(3) 0.393670(18) 0.906893(16) 0.01752(4) Uani d . 1 . .
    Cl Cl23 1.05143(3) 0.336268(18) 0.701995(15) 0.01620(4) Uani d . 1 . .
    Cl Cl24 0.91419(3) 0.134541(17) 0.672205(15) 0.01600(4) Uani d . 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
    C1 C2 . 1.5099(13) ?
    C1 C10 . 1.5623(13) ?
    C1 C13 . 1.5913(13) ?
    C1 H1 . 1 ?
    C2 C3 . 1.4033(14) ?
    C2 C7 . 1.4036(14) ?
    C3 C4 . 1.3919(15) ?
    C3 H3 . 0.95 ?
    C4 C5 . 1.3908(17) ?
    C4 H4 . 0.95 ?
    C5 C6 . 1.3907(15) ?
    C5 H5 . 0.95 ?
    C6 C7 . 1.4035(14) ?
    C6 H6 . 0.95 ?
    C7 C8 . 1.5163(13) ?
    C8 C9 . 1.5655(13) ?
    C8 C18 . 1.5980(13) ?
    C8 H8 . 1 ?
    C9 C10 . 1.5305(13) ?
    C9 C16 . 1.5625(13) ?
    C9 H9 . 1 ?
    C10 C11 . 1.5633(13) ?
    C10 H10 . 1 ?
    C11 C15 . 1.5265(14) ?
    C11 C12 . 1.5543(13) ?
    C11 Cl6 . 1.7535(10) ?
    C12 C13 . 1.5506(14) ?
    C12 Cl1 . 1.7664(10) ?
    C12 Cl2 . 1.7716(10) ?
    C13 C14 . 1.5185(14) ?
    C13 Cl3 . 1.7505(9) ?
    C14 C15 . 1.3403(13) ?
    C14 Cl4 . 1.6926(10) ?
    C15 Cl5 . 1.6976(10) ?
    C16 C20 . 1.5262(14) ?
    C16 C17 . 1.5517(14) ?
    C16 Cl12 . 1.7518(10) ?
    C17 C18 . 1.5493(14) ?
    C17 Cl7 . 1.7668(11) ?
    C17 Cl8 . 1.7730(10) ?
    C18 C19 . 1.5204(14) ?
    C18 Cl9 . 1.7495(10) ?
    C19 C20 . 1.3395(14) ?
    C19 Cl10 . 1.6943(10) ?
    C20 Cl11 . 1.6980(10) ?
    C21 C22 . 1.5136(14) ?
    C21 C30 . 1.5694(13) ?
    C21 C33 . 1.5949(13) ?
    C21 H21 . 1 ?
    C22 C27 . 1.4037(14) ?
    C22 C23 . 1.4046(14) ?
    C23 C24 . 1.3885(17) ?
    C23 H23 . 0.95 ?
    C24 C25 . 1.391(2) ?
    C24 H24 . 0.95 ?
    C25 C26 . 1.3891(17) ?
    C25 H25 . 0.95 ?
    C26 C27 . 1.4026(15) ?
    C26 H26 . 0.95 ?
    C27 C28 . 1.5070(14) ?
    C28 C29 . 1.5643(13) ?
    C28 C38 . 1.5951(14) ?
    C28 H28 . 1 ?
    C29 C30 . 1.5366(13) ?
    C29 C36 . 1.5673(13) ?
    C29 H29 . 1 ?
    C30 C31 . 1.5622(13) ?
    C30 H30 . 1 ?
    C31 C35 . 1.5233(15) ?
    C31 C32 . 1.5554(14) ?
    C31 Cl18 . 1.7531(10) ?
    C32 C33 . 1.5484(13) ?
    C32 Cl13 . 1.7685(10) ?
    C32 Cl14 . 1.7695(10) ?
    C33 C34 . 1.5183(13) ?
    C33 Cl15 . 1.7472(9) ?
    C34 C35 . 1.3398(14) ?
    C34 Cl16 . 1.6902(10) ?
    C35 Cl17 . 1.6943(10) ?
    C36 C40 . 1.5256(14) ?
    C36 C37 . 1.5544(13) ?
    C36 Cl24 . 1.7514(10) ?
    C37 C38 . 1.5459(14) ?
    C37 Cl19 . 1.7648(10) ?
    C37 Cl20 . 1.7744(10) ?
    C38 C39 . 1.5202(14) ?
    C38 Cl21 . 1.7492(10) ?
    C39 C40 . 1.3390(14) ?
    C39 Cl22 . 1.6915(10) ?
    C40 Cl23 . 1.6995(10) ?
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
    C2 C1 C10 . . 116.62(8) ?
    C2 C1 C13 . . 109.50(8) ?
    C10 C1 C13 . . 101.60(7) ?
    C2 C1 H1 . . 109.6 ?
    C10 C1 H1 . . 109.6 ?
    C13 C1 H1 . . 109.6 ?
    C3 C2 C7 . . 119.20(9) ?
    C3 C2 C1 . . 117.67(8) ?
    C7 C2 C1 . . 122.78(8) ?
    C4 C3 C2 . . 120.93(10) ?
    C4 C3 H3 . . 119.5 ?
    C2 C3 H3 . . 119.5 ?
    C5 C4 C3 . . 119.68(10) ?
    C5 C4 H4 . . 120.2 ?
    C3 C4 H4 . . 120.2 ?
    C6 C5 C4 . . 119.63(10) ?
    C6 C5 H5 . . 120.2 ?
    C4 C5 H5 . . 120.2 ?
    C5 C6 C7 . . 121.21(10) ?
    C5 C6 H6 . . 119.4 ?
    C7 C6 H6 . . 119.4 ?
    C6 C7 C2 . . 118.77(9) ?
    C6 C7 C8 . . 118.72(9) ?
    C2 C7 C8 . . 122.16(8) ?
    C7 C8 C9 . . 115.90(8) ?
    C7 C8 C18 . . 109.08(8) ?
    C9 C8 C18 . . 101.61(7) ?
    C7 C8 H8 . . 110 ?
    C9 C8 H8 . . 110 ?
    C18 C8 H8 . . 110 ?
    C10 C9 C16 . . 112.28(8) ?
    C10 C9 C8 . . 119.29(8) ?
    C16 C9 C8 . . 102.75(7) ?
    C10 C9 H9 . . 107.3 ?
    C16 C9 H9 . . 107.3 ?
    C8 C9 H9 . . 107.3 ?
    C9 C10 C1 . . 117.92(8) ?
    C9 C10 C11 . . 111.87(8) ?
    C1 C10 C11 . . 103.20(7) ?
    C9 C10 H10 . . 107.8 ?
    C1 C10 H10 . . 107.8 ?
    C11 C10 H10 . . 107.8 ?
    C15 C11 C12 . . 99.75(7) ?
    C15 C11 C10 . . 107.59(8) ?
    C12 C11 C10 . . 101.23(7) ?
    C15 C11 Cl6 . . 115.79(7) ?
    C12 C11 Cl6 . . 115.87(7) ?
    C10 C11 Cl6 . . 114.67(6) ?
    C13 C12 C11 . . 92.42(7) ?
    C13 C12 Cl1 . . 113.60(7) ?
    C11 C12 Cl1 . . 114.64(7) ?
    C13 C12 Cl2 . . 113.77(7) ?
    C11 C12 Cl2 . . 113.72(7) ?
    Cl1 C12 Cl2 . . 108.22(5) ?
    C14 C13 C12 . . 99.82(8) ?
    C14 C13 C1 . . 106.03(7) ?
    C12 C13 C1 . . 102.45(7) ?
    C14 C13 Cl3 . . 115.75(7) ?
    C12 C13 Cl3 . . 114.89(7) ?
    C1 C13 Cl3 . . 115.87(7) ?
    C15 C14 C13 . . 107.20(8) ?
    C15 C14 Cl4 . . 128.20(8) ?
    C13 C14 Cl4 . . 124.28(7) ?
    C14 C15 C11 . . 107.22(8) ?
    C14 C15 Cl5 . . 127.72(8) ?
    C11 C15 Cl5 . . 124.79(7) ?
    C20 C16 C17 . . 99.79(8) ?
    C20 C16 C9 . . 108.31(8) ?
    C17 C16 C9 . . 100.91(8) ?
    C20 C16 Cl12 . . 115.58(7) ?
    C17 C16 Cl12 . . 116.17(7) ?
    C9 C16 Cl12 . . 114.22(7) ?
    C18 C17 C16 . . 92.43(7) ?
    C18 C17 Cl7 . . 112.78(7) ?
    C16 C17 Cl7 . . 114.95(7) ?
    C18 C17 Cl8 . . 114.39(7) ?
    C16 C17 Cl8 . . 114.08(7) ?
    Cl7 C17 Cl8 . . 107.83(5) ?
    C19 C18 C17 . . 99.77(8) ?
    C19 C18 C8 . . 105.71(7) ?
    C17 C18 C8 . . 102.71(7) ?
    C19 C18 Cl9 . . 116.46(7) ?
    C17 C18 Cl9 . . 114.10(7) ?
    C8 C18 Cl9 . . 116.01(7) ?
    C20 C19 C18 . . 106.61(8) ?
    C20 C19 Cl10 . . 128.56(8) ?
    C18 C19 Cl10 . . 124.41(7) ?
    C19 C20 C16 . . 107.69(8) ?
    C19 C20 Cl11 . . 127.26(8) ?
    C16 C20 Cl11 . . 124.64(7) ?
    C22 C21 C30 . . 116.46(8) ?
    C22 C21 C33 . . 109.13(8) ?
    C30 C21 C33 . . 101.61(7) ?
    C22 C21 H21 . . 109.8 ?
    C30 C21 H21 . . 109.8 ?
    C33 C21 H21 . . 109.8 ?
    C27 C22 C23 . . 118.69(9) ?
    C27 C22 C21 . . 122.21(9) ?
    C23 C22 C21 . . 118.77(9) ?
    C24 C23 C22 . . 120.94(11) ?
    C24 C23 H23 . . 119.5 ?
    C22 C23 H23 . . 119.5 ?
    C23 C24 C25 . . 119.96(11) ?
    C23 C24 H24 . . 120 ?
    C25 C24 H24 . . 120 ?
    C26 C25 C24 . . 119.55(11) ?
    C26 C25 H25 . . 120.2 ?
    C24 C25 H25 . . 120.2 ?
    C25 C26 C27 . . 120.86(11) ?
    C25 C26 H26 . . 119.6 ?
    C27 C26 H26 . . 119.6 ?
    C26 C27 C22 . . 119.35(10) ?
    C26 C27 C28 . . 117.94(9) ?
    C22 C27 C28 . . 122.23(9) ?
    C27 C28 C29 . . 116.94(8) ?
    C27 C28 C38 . . 109.12(8) ?
    C29 C28 C38 . . 101.68(7) ?
    C27 C28 H28 . . 109.6 ?
    C29 C28 H28 . . 109.6 ?
    C38 C28 H28 . . 109.6 ?
    C30 C29 C28 . . 118.17(8) ?
    C30 C29 C36 . . 110.65(8) ?
    C28 C29 C36 . . 102.98(7) ?
    C30 C29 H29 . . 108.2 ?
    C28 C29 H29 . . 108.2 ?
    C36 C29 H29 . . 108.2 ?
    C29 C30 C31 . . 113.40(8) ?
    C29 C30 C21 . . 118.58(8) ?
    C31 C30 C21 . . 102.81(7) ?
    C29 C30 H30 . . 107.1 ?
    C31 C30 H30 . . 107.1 ?
    C21 C30 H30 . . 107.1 ?
    C35 C31 C32 . . 99.48(8) ?
    C35 C31 C30 . . 108.49(8) ?
    C32 C31 C30 . . 100.82(7) ?
    C35 C31 Cl18 . . 115.94(7) ?
    C32 C31 Cl18 . . 115.82(7) ?
    C30 C31 Cl18 . . 114.34(7) ?
    C33 C32 C31 . . 92.48(7) ?
    C33 C32 Cl13 . . 112.85(7) ?
    C31 C32 Cl13 . . 114.98(7) ?
    C33 C32 Cl14 . . 114.30(7) ?
    C31 C32 Cl14 . . 113.66(7) ?
    Cl13 C32 Cl14 . . 108.13(5) ?
    C34 C33 C32 . . 99.98(7) ?
    C34 C33 C21 . . 105.85(7) ?
    C32 C33 C21 . . 102.54(7) ?
    C34 C33 Cl15 . . 116.02(7) ?
    C32 C33 Cl15 . . 114.41(7) ?
    C21 C33 Cl15 . . 116.01(6) ?
    C35 C34 C33 . . 106.63(8) ?
    C35 C34 Cl16 . . 128.68(8) ?
    C33 C34 Cl16 . . 124.37(7) ?
    C34 C35 C31 . . 107.86(8) ?
    C34 C35 Cl17 . . 127.52(8) ?
    C31 C35 Cl17 . . 124.34(7) ?
    C40 C36 C37 . . 100.05(7) ?
    C40 C36 C29 . . 106.76(8) ?
    C37 C36 C29 . . 101.62(8) ?
    C40 C36 Cl24 . . 115.80(7) ?
    C37 C36 Cl24 . . 115.92(7) ?
    C29 C36 Cl24 . . 114.76(6) ?
    C38 C37 C36 . . 92.52(7) ?
    C38 C37 Cl19 . . 113.76(7) ?
    C36 C37 Cl19 . . 114.29(7) ?
    C38 C37 Cl20 . . 113.72(7) ?
    C36 C37 Cl20 . . 114.20(7) ?
    Cl19 C37 Cl20 . . 107.95(5) ?
    C39 C38 C37 . . 100.27(8) ?
    C39 C38 C28 . . 105.99(8) ?
    C37 C38 C28 . . 101.98(7) ?
    C39 C38 Cl21 . . 115.08(7) ?
    C37 C38 Cl21 . . 114.92(7) ?
    C28 C38 Cl21 . . 116.56(7) ?
    C40 C39 C38 . . 107.24(8) ?
    C40 C39 Cl22 . . 128.51(8) ?
    C38 C39 Cl22 . . 123.90(7) ?
    C39 C40 C36 . . 107.17(8) ?
    C39 C40 Cl23 . . 127.44(8) ?
    C36 C40 Cl23 . . 124.86(7) ?
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
    C10 C1 C2 C3 . . . . -173.50(9) ?
    C13 C1 C2 C3 . . . . 71.92(11) ?
    C10 C1 C2 C7 . . . . 13.41(13) ?
    C13 C1 C2 C7 . . . . -101.18(10) ?
    C7 C2 C3 C4 . . . . 5.48(16) ?
    C1 C2 C3 C4 . . . . -167.88(10) ?
    C2 C3 C4 C5 . . . . 1.35(18) ?
    C3 C4 C5 C6 . . . . -4.92(18) ?
    C4 C5 C6 C7 . . . . 1.69(18) ?
    C5 C6 C7 C2 . . . . 5.11(16) ?
    C5 C6 C7 C8 . . . . -168.25(10) ?
    C3 C2 C7 C6 . . . . -8.57(15) ?
    C1 C2 C7 C6 . . . . 164.42(9) ?
    C3 C2 C7 C8 . . . . 164.54(9) ?
    C1 C2 C7 C8 . . . . -22.46(15) ?
    C6 C7 C8 C9 . . . . -178.35(9) ?
    C2 C7 C8 C9 . . . . 8.53(13) ?
    C6 C7 C8 C18 . . . . 67.77(11) ?
    C2 C7 C8 C18 . . . . -105.35(10) ?
    C7 C8 C9 C10 . . . . 13.07(12) ?
    C18 C8 C9 C10 . . . . 131.16(8) ?
    C7 C8 C9 C16 . . . . -111.87(9) ?
    C18 C8 C9 C16 . . . . 6.21(9) ?
    C16 C9 C10 C1 . . . . 99.28(9) ?
    C8 C9 C10 C1 . . . . -20.94(12) ?
    C16 C9 C10 C11 . . . . -141.30(8) ?
    C8 C9 C10 C11 . . . . 98.47(10) ?
    C2 C1 C10 C9 . . . . 8.32(12) ?
    C13 C1 C10 C9 . . . . 127.27(8) ?
    C2 C1 C10 C11 . . . . -115.55(9) ?
    C13 C1 C10 C11 . . . . 3.40(9) ?
    C9 C10 C11 C15 . . . . -63.17(9) ?
    C1 C10 C11 C15 . . . . 64.59(9) ?
    C9 C10 C11 C12 . . . . -167.29(7) ?
    C1 C10 C11 C12 . . . . -39.54(9) ?
    C9 C10 C11 Cl6 . . . . 67.21(9) ?
    C1 C10 C11 Cl6 . . . . -165.03(6) ?
    C15 C11 C12 C13 . . . . -51.76(8) ?
    C10 C11 C12 C13 . . . . 58.53(8) ?
    Cl6 C11 C12 C13 . . . . -176.78(7) ?
    C15 C11 C12 Cl1 . . . . -169.16(6) ?
    C10 C11 C12 Cl1 . . . . -58.87(8) ?
    Cl6 C11 C12 Cl1 . . . . 65.82(9) ?
    C15 C11 C12 Cl2 . . . . 65.58(8) ?
    C10 C11 C12 Cl2 . . . . 175.87(6) ?
    Cl6 C11 C12 Cl2 . . . . -59.44(9) ?
    C11 C12 C13 C14 . . . . 52.50(8) ?
    Cl1 C12 C13 C14 . . . . 170.78(6) ?
    Cl2 C12 C13 C14 . . . . -64.80(8) ?
    C11 C12 C13 C1 . . . . -56.48(8) ?
    Cl1 C12 C13 C1 . . . . 61.80(8) ?
    Cl2 C12 C13 C1 . . . . -173.78(6) ?
    C11 C12 C13 Cl3 . . . . 177.01(7) ?
    Cl1 C12 C13 Cl3 . . . . -64.72(8) ?
    Cl2 C12 C13 Cl3 . . . . 59.71(9) ?
    C2 C1 C13 C14 . . . . 53.64(9) ?
    C10 C1 C13 C14 . . . . -70.27(8) ?
    C2 C1 C13 C12 . . . . 157.83(8) ?
    C10 C1 C13 C12 . . . . 33.93(9) ?
    C2 C1 C13 Cl3 . . . . -76.28(9) ?
    C10 C1 C13 Cl3 . . . . 159.81(6) ?
    C12 C13 C14 C15 . . . . -35.79(10) ?
    C1 C13 C14 C15 . . . . 70.31(10) ?
    Cl3 C13 C14 C15 . . . . -159.70(7) ?
    C12 C13 C14 Cl4 . . . . 150.16(8) ?
    C1 C13 C14 Cl4 . . . . -103.74(9) ?
    Cl3 C13 C14 Cl4 . . . . 26.25(11) ?
    C13 C14 C15 C11 . . . . 1.03(11) ?
    Cl4 C14 C15 C11 . . . . 174.77(8) ?
    C13 C14 C15 Cl5 . . . . -173.21(8) ?
    Cl4 C14 C15 Cl5 . . . . 0.53(15) ?
    C12 C11 C15 C14 . . . . 33.98(10) ?
    C10 C11 C15 C14 . . . . -71.19(10) ?
    Cl6 C11 C15 C14 . . . . 159.06(7) ?
    C12 C11 C15 Cl5 . . . . -151.57(8) ?
    C10 C11 C15 Cl5 . . . . 103.26(9) ?
    Cl6 C11 C15 Cl5 . . . . -26.49(11) ?
    C10 C9 C16 C20 . . . . -67.18(10) ?
    C8 C9 C16 C20 . . . . 62.24(9) ?
    C10 C9 C16 C17 . . . . -171.43(8) ?
    C8 C9 C16 C17 . . . . -42.02(9) ?
    C10 C9 C16 Cl12 . . . . 63.17(9) ?
    C8 C9 C16 Cl12 . . . . -167.41(6) ?
    C20 C16 C17 C18 . . . . -51.30(8) ?
    C9 C16 C17 C18 . . . . 59.68(8) ?
    Cl12 C16 C17 C18 . . . . -176.26(7) ?
    C20 C16 C17 Cl7 . . . . -167.86(7) ?
    C9 C16 C17 Cl7 . . . . -56.89(9) ?
    Cl12 C16 C17 Cl7 . . . . 67.18(9) ?
    C20 C16 C17 Cl8 . . . . 66.84(8) ?
    C9 C16 C17 Cl8 . . . . 177.82(6) ?
    Cl12 C16 C17 Cl8 . . . . -58.12(9) ?
    C16 C17 C18 C19 . . . . 53.07(8) ?
    Cl7 C17 C18 C19 . . . . 171.48(6) ?
    Cl8 C17 C18 C19 . . . . -64.80(8) ?
    C16 C17 C18 C8 . . . . -55.62(8) ?
    Cl7 C17 C18 C8 . . . . 62.79(8) ?
    Cl8 C17 C18 C8 . . . . -173.50(6) ?
    C16 C17 C18 Cl9 . . . . 177.98(7) ?
    Cl7 C17 C18 Cl9 . . . . -63.61(8) ?
    Cl8 C17 C18 Cl9 . . . . 60.10(9) ?
    C7 C8 C18 C19 . . . . 50.31(10) ?
    C9 C8 C18 C19 . . . . -72.58(9) ?
    C7 C8 C18 C17 . . . . 154.44(8) ?
    C9 C8 C18 C17 . . . . 31.56(9) ?
    C7 C8 C18 Cl9 . . . . -80.40(9) ?
    C9 C8 C18 Cl9 . . . . 156.71(7) ?
    C17 C18 C19 C20 . . . . -37.05(10) ?
    C8 C18 C19 C20 . . . . 69.24(10) ?
    Cl9 C18 C19 C20 . . . . -160.31(7) ?
    C17 C18 C19 Cl10 . . . . 149.88(7) ?
    C8 C18 C19 Cl10 . . . . -103.83(9) ?
    Cl9 C18 C19 Cl10 . . . . 26.62(11) ?
    C18 C19 C20 C16 . . . . 2.56(10) ?
    Cl10 C19 C20 C16 . . . . 175.25(8) ?
    C18 C19 C20 Cl11 . . . . -170.33(7) ?
    Cl10 C19 C20 Cl11 . . . . 2.35(15) ?
    C17 C16 C20 C19 . . . . 32.74(10) ?
    C9 C16 C20 C19 . . . . -72.30(10) ?
    Cl12 C16 C20 C19 . . . . 158.11(7) ?
    C17 C16 C20 Cl11 . . . . -154.13(7) ?
    C9 C16 C20 Cl11 . . . . 100.83(9) ?
    Cl12 C16 C20 Cl11 . . . . -28.77(11) ?
    C30 C21 C22 C27 . . . . -8.24(14) ?
    C33 C21 C22 C27 . . . . 106.00(10) ?
    C30 C21 C22 C23 . . . . 178.47(9) ?
    C33 C21 C22 C23 . . . . -67.29(12) ?
    C27 C22 C23 C24 . . . . -5.27(16) ?
    C21 C22 C23 C24 . . . . 168.26(10) ?
    C22 C23 C24 C25 . . . . -2.09(19) ?
    C23 C24 C25 C26 . . . . 5.7(2) ?
    C24 C25 C26 C27 . . . . -1.98(19) ?
    C25 C26 C27 C22 . . . . -5.41(17) ?
    C25 C26 C27 C28 . . . . 166.77(11) ?
    C23 C22 C27 C26 . . . . 8.92(15) ?
    C21 C22 C27 C26 . . . . -164.38(10) ?
    C23 C22 C27 C28 . . . . -162.92(10) ?
    C21 C22 C27 C28 . . . . 23.78(15) ?
    C26 C27 C28 C29 . . . . 171.49(9) ?
    C22 C27 C28 C29 . . . . -16.56(14) ?
    C26 C27 C28 C38 . . . . -73.90(12) ?
    C22 C27 C28 C38 . . . . 98.05(11) ?
    C27 C28 C29 C30 . . . . -5.02(12) ?
    C38 C28 C29 C30 . . . . -123.72(9) ?
    C27 C28 C29 C36 . . . . 117.26(9) ?
    C38 C28 C29 C36 . . . . -1.44(9) ?
    C28 C29 C30 C31 . . . . -101.76(10) ?
    C36 C29 C30 C31 . . . . 139.94(8) ?
    C28 C29 C30 C21 . . . . 18.97(12) ?
    C36 C29 C30 C21 . . . . -99.33(10) ?
    C22 C21 C30 C29 . . . . -12.98(12) ?
    C33 C21 C30 C29 . . . . -131.41(8) ?
    C22 C21 C30 C31 . . . . 113.02(9) ?
    C33 C21 C30 C31 . . . . -5.41(9) ?
    C29 C30 C31 C35 . . . . 66.67(10) ?
    C21 C30 C31 C35 . . . . -62.61(9) ?
    C29 C30 C31 C32 . . . . 170.59(8) ?
    C21 C30 C31 C32 . . . . 41.31(9) ?
    C29 C30 C31 Cl18 . . . . -64.44(10) ?
    C21 C30 C31 Cl18 . . . . 166.28(7) ?
    C35 C31 C32 C33 . . . . 51.48(8) ?
    C30 C31 C32 C33 . . . . -59.58(8) ?
    Cl18 C31 C32 C33 . . . . 176.46(7) ?
    C35 C31 C32 Cl13 . . . . 168.16(6) ?
    C30 C31 C32 Cl13 . . . . 57.11(9) ?
    Cl18 C31 C32 Cl13 . . . . -66.86(9) ?
    C35 C31 C32 Cl14 . . . . -66.47(8) ?
    C30 C31 C32 Cl14 . . . . -177.53(6) ?
    Cl18 C31 C32 Cl14 . . . . 58.51(9) ?
    C31 C32 C33 C34 . . . . -52.74(8) ?
    Cl13 C32 C33 C34 . . . . -171.23(6) ?
    Cl14 C32 C33 C34 . . . . 64.66(8) ?
    C31 C32 C33 C21 . . . . 56.12(8) ?
    Cl13 C32 C33 C21 . . . . -62.37(8) ?
    Cl14 C32 C33 C21 . . . . 173.52(6) ?
    C31 C32 C33 Cl15 . . . . -177.42(6) ?
    Cl13 C32 C33 Cl15 . . . . 64.09(8) ?
    Cl14 C32 C33 Cl15 . . . . -60.01(9) ?
    C22 C21 C33 C34 . . . . -51.60(10) ?
    C30 C21 C33 C34 . . . . 71.95(9) ?
    C22 C21 C33 C32 . . . . -155.94(8) ?
    C30 C21 C33 C32 . . . . -32.39(9) ?
    C22 C21 C33 Cl15 . . . . 78.63(9) ?
    C30 C21 C33 Cl15 . . . . -157.82(7) ?
    C32 C33 C34 C35 . . . . 36.13(10) ?
    C21 C33 C34 C35 . . . . -70.08(10) ?
    Cl15 C33 C34 C35 . . . . 159.69(7) ?
    C32 C33 C34 Cl16 . . . . -149.88(7) ?
    C21 C33 C34 Cl16 . . . . 103.91(9) ?
    Cl15 C33 C34 Cl16 . . . . -26.32(11) ?
    C33 C34 C35 C31 . . . . -1.40(11) ?
    Cl16 C34 C35 C31 . . . . -175.04(8) ?
    C33 C34 C35 Cl17 . . . . 172.77(8) ?
    Cl16 C34 C35 Cl17 . . . . -0.88(15) ?
    C32 C31 C35 C34 . . . . -33.58(10) ?
    C30 C31 C35 C34 . . . . 71.28(10) ?
    Cl18 C31 C35 C34 . . . . -158.48(7) ?
    C32 C31 C35 Cl17 . . . . 152.03(7) ?
    C30 C31 C35 Cl17 . . . . -103.11(9) ?
    Cl18 C31 C35 Cl17 . . . . 27.12(11) ?
    C30 C29 C36 C40 . . . . 60.71(9) ?
    C28 C29 C36 C40 . . . . -66.49(9) ?
    C30 C29 C36 C37 . . . . 165.07(8) ?
    C28 C29 C36 C37 . . . . 37.87(9) ?
    C30 C29 C36 Cl24 . . . . -69.04(9) ?
    C28 C29 C36 Cl24 . . . . 163.76(6) ?
    C40 C36 C37 C38 . . . . 51.35(8) ?
    C29 C36 C37 C38 . . . . -58.25(8) ?
    Cl24 C36 C37 C38 . . . . 176.64(7) ?
    C40 C36 C37 Cl19 . . . . 168.89(7) ?
    C29 C36 C37 Cl19 . . . . 59.29(9) ?
    Cl24 C36 C37 Cl19 . . . . -65.83(9) ?
    C40 C36 C37 Cl20 . . . . -66.11(9) ?
    C29 C36 C37 Cl20 . . . . -175.71(6) ?
    Cl24 C36 C37 Cl20 . . . . 59.17(9) ?
    C36 C37 C38 C39 . . . . -51.74(8) ?
    Cl19 C37 C38 C39 . . . . -169.73(6) ?
    Cl20 C37 C38 C39 . . . . 66.13(8) ?
    C36 C37 C38 C28 . . . . 57.20(8) ?
    Cl19 C37 C38 C28 . . . . -60.78(8) ?
    Cl20 C37 C38 C28 . . . . 175.07(6) ?
    C36 C37 C38 Cl21 . . . . -175.75(7) ?
    Cl19 C37 C38 Cl21 . . . . 66.27(8) ?
    Cl20 C37 C38 Cl21 . . . . -57.87(9) ?
    C27 C28 C38 C39 . . . . -55.30(10) ?
    C29 C28 C38 C39 . . . . 68.84(9) ?
    C27 C28 C38 C37 . . . . -159.80(8) ?
    C29 C28 C38 C37 . . . . -35.66(9) ?
    C27 C28 C38 Cl21 . . . . 74.21(9) ?
    C29 C28 C38 Cl21 . . . . -161.65(7) ?
    C37 C38 C39 C40 . . . . 35.04(10) ?
    C28 C38 C39 C40 . . . . -70.71(10) ?
    Cl21 C38 C39 C40 . . . . 158.93(8) ?
    C37 C38 C39 Cl22 . . . . -151.30(8) ?
    C28 C38 C39 Cl22 . . . . 102.96(9) ?
    Cl21 C38 C39 Cl22 . . . . -27.41(11) ?
    C38 C39 C40 C36 . . . . -0.47(11) ?
    Cl22 C39 C40 C36 . . . . -173.75(8) ?
    C38 C39 C40 Cl23 . . . . 171.46(8) ?
    Cl22 C39 C40 Cl23 . . . . -1.82(16) ?
    C37 C36 C40 C39 . . . . -34.02(10) ?
    C29 C36 C40 C39 . . . . 71.46(10) ?
    Cl24 C36 C40 C39 . . . . -159.39(7) ?
    C37 C36 C40 Cl23 . . . . 153.79(8) ?
    C29 C36 C40 Cl23 . . . . -100.73(9) ?
    Cl24 C36 C40 Cl23 . . . . 28.42(11) ?
