#------------------------------------------------------------------------------
#$Date: 2015-09-06 01:30:16 +0300 (Sun, 06 Sep 2015) $
#$Revision: 154622 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/37/4123749.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4123749
loop_
_publ_author_name
'Cao, Jing'
'London, Gábor'
'Dumele, Oliver'
'von Wantoch Rekowski, Margarete'
'Trapp, Nils'
'Ruhlmann, Laurent'
'Boudon, Corinne'
'Stanger, Amnon'
'Diederich, François'
_publ_section_title
;
 The Impact of Antiaromatic Subunits in [4n+2] π-Systems: Bispentalenes
 with [4n+2] π-Electron Perimeters and Antiaromatic Character.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7178
_journal_page_last               7188
_journal_paper_doi               10.1021/jacs.5b03074
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C74 H76 O4, 6(C D Cl3)'
_chemical_formula_sum            'C80 H76 Cl18 D6 O4'
_chemical_formula_weight         1751.50
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                90
_cell_angle_beta                 121.225(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.3401(9)
_cell_length_b                   10.9180(7)
_cell_length_c                   27.3803(15)
_cell_measurement_reflns_used    1737
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.55
_cell_volume                     4177.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            43845
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.473
_diffrn_reflns_theta_min         2.246
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0526 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.9375. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       plate
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.449
_refine_diff_density_min         -1.450
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.435
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         8604
_refine_ls_number_restraints     626
_refine_ls_restrained_S_all      1.421
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0937
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1235P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2551
_refine_ls_wR_factor_ref         0.2868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5194
_reflns_number_total             8604
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b03074_si_001.cif
_cod_data_source_block           2b
_cod_depositor_comments
'Adding full bibliography for 4123748--4123750.cif.'
_cod_database_code               4123749
_shelxl_version_number           2013-4
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl17-Cl18
 2.931 with sigma of 0.02
 Cl17-Cl16
 2.931 with sigma of 0.02
 Cl18-Cl16
 2.931 with sigma of 0.02
 Cl1A-Cl16
 2.931 with sigma of 0.02
 Cl1A-Cl1B
 2.931 with sigma of 0.02
 Cl1B-Cl16
 2.931 with sigma of 0.02
 Cl1A-D7
 2.35 with sigma of 0.02
 Cl16-D7
 2.35 with sigma of 0.02
 C6-D6
 1.09 with sigma of 0.02
 Cl18-D6
 2.35 with sigma of 0.02
 D6-Cl17
 2.35 with sigma of 0.02
 Cl16-C7 = Cl16-C6 = Cl17-C6 = Cl1B-C7 = Cl18-C6 = Cl1A-C7
 1.776 with sigma of 0.02
 Cl16-D6
 2.35 with sigma of 0.02
 Cl1B-D7
 2.35 with sigma of 0.02
 C5-D5 = C7-D7
 1.09 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(Cl17) = Uanis(Cl1B)
Uanis(Cl1A) = Uanis(Cl18)
Uanis(Cl5) = Uanis(Cl14)
Uanis(Cl8) = Uanis(Cl13)
Uanis(Cl7) = Uanis(Cl15)
Uanis(Cl1) = Uanis(Cl5)
Uanis(Cl7) = Uanis(Cl3)
Uanis(C1) = Uanis(C5)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 1*[Sof(Cl1)+Sof(Cl3)+Sof(Cl4)+Sof(C5)+Sof(D5)]+1*[Sof(Cl5)+Sof(Cl7)+Sof(Cl8)+
 Sof(C1)+Sof(D1)]+1*[Sof(Cl9)+Sof(Cl10)+Sof(Cl11)+Sof(C2)+Sof(D2)]+1*[Sof(Cl13)+
 Sof(Cl14)+Sof(Cl15)+Sof(C3)+Sof(D3)]=1 with esd of 0.001
 Sof(Cl1)=Sof(Cl3)=Sof(Cl4)=Sof(C5)=Sof(D5)=FVAR(1)
 Sof(Cl5)=Sof(Cl7)=Sof(Cl8)=Sof(C1)=Sof(D1)=FVAR(2)
 Sof(Cl9)=Sof(Cl10)=Sof(Cl11)=Sof(C2)=Sof(D2)=FVAR(3)
 Sof(Cl13)=Sof(Cl14)=Sof(Cl15)=Sof(C3)=Sof(D3)=FVAR(4)
 Sof(Cl1A)=Sof(Cl1B)=Sof(C7)=Sof(D7)=1-FVAR(5)
 Sof(Cl17)=Sof(Cl18)=Sof(C6)=Sof(D6)=FVAR(5)
7.a Free rotating group:
 Cl1(Cl3,Cl4,C5,D5), Cl5(Cl7,Cl8,C1,D1), Cl9(Cl10,Cl11,C2,D2), Cl13(Cl14,Cl15,
 C3,D3)
7.b Ternary CH refined with riding coordinates:
 C48(D48)
7.c Secondary CH2 refined with riding coordinates:
 C57(H57A,H57B)
7.d Aromatic/amide H refined with riding coordinates:
 C74(H74), C76(H76), C82(H82), C99(H99), C108(H108), C127(H127), C133(H133),
 C137(H137), C155(H155), C157(H157), C178(H178), C200(H200)
7.e Idealised Me refined as rotating group:
 C50(H50A,H50B,H50C), C67(H67A,H67B,H67C), C78(H78A,H78B,H78C), C106(H10A,H10B,
 H10C), C166(H16A,H16B,H16C), C181(H18A,H18B,H18C), C195(H19A,H19B,H19C),
 C4(H4A,H4B,H4C)
;
_olex2_computing_structure_refinement_long 'SHELXL-97 (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'SHELXS-97 (Sheldrick, 2008)'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O39 O -0.5199(2) 0.5495(3) 0.09987(14) 0.0269(8) Uani 1 1 d . U . . .
O42 O -0.0188(3) 0.3757(3) 0.11061(16) 0.0303(8) Uani 1 1 d . U . . .
C50 C 0.3414(4) 0.0825(5) 0.4606(2) 0.0341(13) Uani 1 1 d . U . . .
H50A H 0.2848 0.0407 0.4301 0.051 Uiso 1 1 calc GR . . . .
H50B H 0.3796 0.0245 0.4915 0.051 Uiso 1 1 calc GR . . . .
H50C H 0.3799 0.1144 0.4455 0.051 Uiso 1 1 calc GR . . . .
C52 C 0.3096(3) 0.1891(5) 0.4838(2) 0.0248(11) Uani 1 1 d . U . . .
C57 C -0.0110(3) 0.2918(4) 0.1955(2) 0.0201(10) Uani 1 1 d . U . . .
H57A H -0.0482 0.2184 0.1746 0.024 Uiso 1 1 calc R . . . .
H57B H 0.0574 0.2712 0.2123 0.024 Uiso 1 1 calc R . . . .
C67 C 0.2531(4) 0.1352(5) 0.5083(2) 0.0327(13) Uani 1 1 d . U . . .
H67A H 0.2958 0.0862 0.5422 0.049 Uiso 1 1 calc GR . . . .
H67B H 0.2020 0.0829 0.4796 0.049 Uiso 1 1 calc GR . . . .
H67C H 0.2251 0.2015 0.5191 0.049 Uiso 1 1 calc GR . . . .
C74 C -0.0877(3) 0.5113(4) 0.2046(2) 0.0180(9) Uani 1 1 d . U . . .
H74 H -0.1155 0.5858 0.2070 0.022 Uiso 1 1 calc R . . . .
C76 C -0.3123(3) 0.5853(4) 0.2457(2) 0.0192(10) Uani 1 1 d . U . . .
H76 H -0.2915 0.6328 0.2792 0.023 Uiso 1 1 calc R . . . .
C78 C 0.3970(4) 0.2542(5) 0.5310(2) 0.0346(13) Uani 1 1 d . U . . .
H78A H 0.3766 0.3187 0.5473 0.052 Uiso 1 1 calc GR . . . .
H78B H 0.4333 0.2908 0.5154 0.052 Uiso 1 1 calc GR . . . .
H78C H 0.4374 0.1952 0.5609 0.052 Uiso 1 1 calc GR . . . .
C82 C -0.2846(3) 0.4276(4) 0.1959(2) 0.0194(10) Uani 1 1 d . U . . .
H82 H -0.2444 0.3660 0.1948 0.023 Uiso 1 1 calc R . . . .
C83 C -0.2517(3) 0.4965(4) 0.24504(19) 0.0156(9) Uani 1 1 d . U . . .
C91 C -0.1293(3) 0.4884(4) 0.3547(2) 0.0183(9) Uani 1 1 d . U . . .
C99 C -0.4034(3) 0.6057(4) 0.1979(2) 0.0193(10) Uani 1 1 d . U . . .
H99 H -0.4440 0.6665 0.1990 0.023 Uiso 1 1 calc R . . . .
C106 C 0.2395(4) 0.4137(6) 0.2709(2) 0.0349(13) Uani 1 1 d . U . . .
H10A H 0.2705 0.4428 0.2506 0.052 Uiso 1 1 calc GR . . . .
H10B H 0.1715 0.4357 0.2492 0.052 Uiso 1 1 calc GR . . . .
H10C H 0.2458 0.3245 0.2750 0.052 Uiso 1 1 calc GR . . . .
C108 C -0.3743(3) 0.4460(4) 0.1483(2) 0.0197(10) Uani 1 1 d . U . . .
H108 H -0.3954 0.3973 0.1151 0.024 Uiso 1 1 calc R . . . .
C109 C -0.4339(3) 0.5367(4) 0.1491(2) 0.0182(9) Uani 1 1 d . U . . .
C112 C 0.2505(3) 0.2798(4) 0.4345(2) 0.0207(10) Uani 1 1 d . U . . .
C120 C -0.0628(3) 0.4212(4) 0.24609(19) 0.0160(9) Uani 1 1 d . U . . .
C122 C -0.0281(3) 0.4539(4) 0.3907(2) 0.0182(9) Uani 1 1 d . U . . .
C127 C 0.2913(3) 0.3345(4) 0.4066(2) 0.0213(10) Uani 1 1 d . U . . .
H127 H 0.3552 0.3133 0.4180 0.026 Uiso 1 1 calc R . . . .
C132 C 0.1057(3) 0.3959(4) 0.37360(19) 0.0155(9) Uani 1 1 d . U . . .
C133 C -0.0722(3) 0.4928(4) 0.1601(2) 0.0208(10) Uani 1 1 d . U . . .
H133 H -0.0885 0.5554 0.1324 0.025 Uiso 1 1 calc R . . . .
C137 C 0.1497(3) 0.4479(4) 0.3465(2) 0.0172(9) Uani 1 1 d . U . . .
H137 H 0.1148 0.5044 0.3163 0.021 Uiso 1 1 calc R . . . .
C144 C -0.0330(3) 0.3841(4) 0.1554(2) 0.0215(10) Uani 1 1 d . U . . .
C147 C -0.1554(3) 0.4772(4) 0.2951(2) 0.0183(9) Uani 1 1 d . U . . .
C155 C -0.0261(3) 0.3114(4) 0.2401(2) 0.0190(10) Uani 1 1 d . U . . .
H155 H -0.0110 0.2482 0.2673 0.023 Uiso 1 1 calc R . . . .
C157 C 0.1569(3) 0.3113(4) 0.4177(2) 0.0184(10) Uani 1 1 d . U . . .
H157 H 0.1275 0.2750 0.4363 0.022 Uiso 1 1 calc R . . . .
C160 C -0.0739(3) 0.4416(4) 0.2955(2) 0.0177(9) Uani 1 1 d . U . . .
C166 C 0.2702(4) 0.6111(5) 0.3229(3) 0.0322(12) Uani 1 1 d . U . . .
H16A H 0.2015 0.6275 0.2985 0.048 Uiso 1 1 calc GR . . . .
H16B H 0.3040 0.6458 0.3051 0.048 Uiso 1 1 calc GR . . . .
H16C H 0.2944 0.6486 0.3604 0.048 Uiso 1 1 calc GR . . . .
C170 C 0.0068(3) 0.4284(4) 0.3563(2) 0.0168(9) Uani 1 1 d . U . . .
C172 C 0.2435(3) 0.4189(4) 0.3628(2) 0.0185(10) Uani 1 1 d . U . . .
C173 C -0.0007(3) 0.4718(4) 0.4502(2) 0.0180(9) Uani 1 1 d . U . . .
C178 C 0.0840(3) 0.4570(4) 0.5019(2) 0.0188(10) Uani 1 1 d . U . . .
H178 H 0.1399 0.4274 0.5034 0.023 Uiso 1 1 calc R . . . .
C181 C 0.0337(4) 0.2715(6) 0.1099(3) 0.0399(15) Uani 1 1 d . U . . .
H18A H 0.0003 0.1964 0.1093 0.060 Uiso 1 1 calc GR . . . .
H18B H 0.0979 0.2721 0.1442 0.060 Uiso 1 1 calc GR . . . .
H18C H 0.0388 0.2745 0.0758 0.060 Uiso 1 1 calc GR . . . .
C188 C 0.2870(3) 0.4729(5) 0.3298(2) 0.0239(11) Uani 1 1 d . U . . .
C192 C -0.0850(3) 0.5134(4) 0.4484(2) 0.0188(10) Uani 1 1 d . U . . .
C195 C 0.3960(4) 0.4527(6) 0.3609(3) 0.0397(15) Uani 1 1 d . U . . .
H19A H 0.4222 0.4987 0.3413 0.060 Uiso 1 1 calc GR . . . .
H19B H 0.4093 0.3653 0.3606 0.060 Uiso 1 1 calc GR . . . .
H19C H 0.4258 0.4813 0.4004 0.060 Uiso 1 1 calc GR . . . .
C200 C -0.1631(3) 0.5219(4) 0.3884(2) 0.0186(10) Uani 1 1 d . U . . .
H200 H -0.2269 0.5469 0.3755 0.022 Uiso 1 1 calc R . . . .
Cl2 Cl 0.40416(10) 0.6336(2) 0.49075(7) 0.0584(5) Uani 1 1 d . U . . .
Cl6 Cl 0.31656(12) 0.57438(15) 0.55510(7) 0.0488(5) Uani 1 1 d . U . . .
Cl12 Cl 0.21316(11) 0.71937(17) 0.45322(8) 0.0610(6) Uani 1 1 d . U . . .
C48 C 0.2952(4) 0.6032(6) 0.4854(3) 0.0359(13) Uani 1 1 d . U . . .
D48 D 0.2677 0.5273 0.4621 0.043 Uiso 1 1 calc R . . . .
C4 C -0.5836(4) 0.6383(5) 0.0999(2) 0.0348(13) Uani 1 1 d . U . . .
H4A H -0.5958 0.6198 0.1306 0.052 Uiso 1 1 calc GR . . . .
H4B H -0.6440 0.6367 0.0631 0.052 Uiso 1 1 calc GR . . . .
H4C H -0.5547 0.7199 0.1061 0.052 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.4096(11) 0.8238(9) 0.7443(6) 0.0390(15) Uani 0.208(6) 1 d . U P A 2
Cl3 Cl 0.4321(10) 0.5992(12) 0.6938(5) 0.0339(15) Uani 0.208(6) 1 d G U P A 2
Cl4 Cl 0.5747(6) 0.6636(16) 0.8120(4) 0.052(3) Uani 0.208(6) 1 d G U P A 2
C5 C 0.4520(5) 0.6704(8) 0.7574(4) 0.029(2) Uani 0.208(6) 1 d DG U P A 2
D5 D 0.4114 0.6197 0.7721 0.035 Uiso 0.208(6) 1 d DG . P A 2
Cl5 Cl 0.3773(4) 0.8061(5) 0.7257(3) 0.0390(15) Uani 0.445(7) 1 d . U P B 1
Cl7 Cl 0.4697(6) 0.5914(3) 0.7106(3) 0.0339(15) Uani 0.445(7) 1 d G U P B 1
Cl8 Cl 0.5630(4) 0.7219(8) 0.81999(14) 0.0534(17) Uani 0.445(7) 1 d G U P B 1
C1 C 0.45205(19) 0.6772(2) 0.75941(12) 0.029(2) Uani 0.445(7) 1 d G U P B 1
D1 D 0.4157 0.6181 0.7744 0.035 Uiso 0.445(7) 1 d G . P B 1
Cl9 Cl 0.5945(11) 0.6148(12) 0.8015(7) 0.137(7) Uani 0.209(6) 1 d . U P C 3
Cl10 Cl 0.4699(15) 0.8260(8) 0.7807(9) 0.128(7) Uani 0.209(6) 1 d G U P C 3
Cl11 Cl 0.4122(12) 0.6366(15) 0.6929(6) 0.149(7) Uani 0.209(6) 1 d G U P C 3
C2 C 0.4745(10) 0.6677(8) 0.7673(6) 0.125(9) Uani 0.209(6) 1 d G U P C 3
D2 D 0.4387 0.6176 0.7854 0.150 Uiso 0.209(6) 1 d G . P C 3
Cl13 Cl 0.5398(11) 0.7744(19) 0.8208(5) 0.0534(17) Uani 0.138(5) 1 d . U P D 4
Cl14 Cl 0.3584(9) 0.7730(16) 0.7108(7) 0.0390(15) Uani 0.138(5) 1 d G U P D 4
Cl15 Cl 0.5081(11) 0.5948(13) 0.7330(7) 0.0339(15) Uani 0.138(5) 1 d G U P D 4
C3 C 0.4540(7) 0.6825(10) 0.7634(5) 0.034(6) Uani 0.138(5) 1 d G U P D 4
D3 D 0.4240 0.6187 0.7807 0.040 Uiso 0.138(5) 1 d G . P D 4
Cl16 Cl 0.12387(16) 0.8398(2) 0.65339(11) 0.0815(7) Uani 1 1 d D U . . .
Cl17 Cl 0.21567(15) 1.0228(2) 0.62448(10) 0.0562(6) Uani 0.803(3) 1 d D U P E 1
Cl18 Cl 0.1134(3) 0.8344(4) 0.54433(18) 0.1432(17) Uani 0.803(3) 1 d D U P E 1
C6 C 0.1139(6) 0.9261(8) 0.5970(4) 0.057(2) Uani 0.803(3) 1 d D U P E 1
D6 D 0.0502(12) 0.9821(19) 0.5779(9) 0.069 Uiso 0.803(3) 1 d DR . P E 1
Cl1A Cl -0.0119(9) 0.8818(17) 0.5339(5) 0.1432(17) Uani 0.197(3) 1 d D U P E 2
Cl1B Cl 0.1878(6) 0.9126(8) 0.5751(4) 0.0562(6) Uani 0.197(3) 1 d D U P E 2
C7 C 0.1017(14) 0.8273(19) 0.5842(8) 0.083(5) Uani 0.197(3) 1 d D U P E 2
D7 D 0.109(2) 0.7322(17) 0.5748(11) 0.100 Uiso 0.197(3) 1 d DR . P E 2
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'
D D 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'
H H 0.0000 0.0000 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C109 O39 C4 116.7(4) . .
C144 O42 C181 116.6(4) . .
H50A C50 H50B 109.5 . .
H50A C50 H50C 109.5 . .
H50B C50 H50C 109.5 . .
C52 C50 H50A 109.5 . .
C52 C50 H50B 109.5 . .
C52 C50 H50C 109.5 . .
C50 C52 C112 108.5(4) . .
C67 C52 C50 107.6(4) . .
C67 C52 C78 108.9(4) . .
C67 C52 C112 112.9(4) . .
C78 C52 C50 109.7(4) . .
C78 C52 C112 109.3(4) . .
H57A C57 H57B 107.0 . .
C144 C57 H57A 107.4 . .
C144 C57 H57B 107.4 . .
C155 C57 H57A 107.4 . .
C155 C57 H57B 107.4 . .
C155 C57 C144 119.5(4) . .
C52 C67 H67A 109.5 . .
C52 C67 H67B 109.5 . .
C52 C67 H67C 109.5 . .
H67A C67 H67B 109.5 . .
H67A C67 H67C 109.5 . .
H67B C67 H67C 109.5 . .
C120 C74 H74 119.8 . .
C133 C74 H74 119.8 . .
C133 C74 C120 120.4(4) . .
C83 C76 H76 119.4 . .
C83 C76 C99 121.1(4) . .
C99 C76 H76 119.4 . .
C52 C78 H78A 109.5 . .
C52 C78 H78B 109.5 . .
C52 C78 H78C 109.5 . .
H78A C78 H78B 109.5 . .
H78A C78 H78C 109.5 . .
H78B C78 H78C 109.5 . .
C83 C82 H82 119.2 . .
C108 C82 H82 119.2 . .
C108 C82 C83 121.7(4) . .
C76 C83 C147 120.8(4) . .
C82 C83 C76 118.1(4) . .
C82 C83 C147 121.1(4) . .
C147 C91 C122 107.7(4) . .
C200 C91 C122 109.2(4) . .
C200 C91 C147 143.1(4) . .
C76 C99 H99 120.2 . .
C109 C99 C76 119.6(4) . .
C109 C99 H99 120.2 . .
H10A C106 H10B 109.5 . .
H10A C106 H10C 109.5 . .
H10B C106 H10C 109.5 . .
C188 C106 H10A 109.5 . .
C188 C106 H10B 109.5 . .
C188 C106 H10C 109.5 . .
C82 C108 H108 120.1 . .
C82 C108 C109 119.8(4) . .
C109 C108 H108 120.1 . .
O39 C109 C99 124.9(4) . .
O39 C109 C108 115.4(4) . .
C99 C109 C108 119.7(4) . .
C127 C112 C52 119.8(4) . .
C127 C112 C157 118.2(4) . .
C157 C112 C52 122.0(4) . .
C74 C120 C160 121.3(4) . .
C155 C120 C74 118.3(4) . .
C155 C120 C160 120.4(4) . .
C170 C122 C91 108.6(4) . .
C170 C122 C173 143.4(4) . .
C173 C122 C91 107.6(4) . .
C112 C127 H127 118.4 . .
C112 C127 C172 123.2(4) . .
C172 C127 H127 118.4 . .
C137 C132 C157 119.0(4) . .
C137 C132 C170 120.9(4) . .
C157 C132 C170 120.1(4) . .
C74 C133 H133 119.6 . .
C74 C133 C144 120.7(5) . .
C144 C133 H133 119.6 . .
C132 C137 H137 119.2 . .
C132 C137 C172 121.6(4) . .
C172 C137 H137 119.2 . .
O42 C144 C57 124.4(4) . .
O42 C144 C133 116.3(4) . .
C133 C144 C57 119.3(4) . .
C91 C147 C83 125.6(4) . .
C160 C147 C83 127.4(4) . .
C160 C147 C91 107.0(4) . .
C57 C155 C120 121.6(4) . .
C57 C155 H155 119.2 . .
C120 C155 H155 119.2 . .
C112 C157 C132 120.7(4) . .
C112 C157 H157 119.6 . .
C132 C157 H157 119.6 . .
C120 C160 C170 123.3(4) . .
C147 C160 C120 127.7(4) . .
C147 C160 C170 108.9(4) . .
H16A C166 H16B 109.5 . .
H16A C166 H16C 109.5 . .
H16B C166 H16C 109.5 . .
C188 C166 H16A 109.5 . .
C188 C166 H16B 109.5 . .
C188 C166 H16C 109.5 . .
C122 C170 C132 127.8(4) . .
C122 C170 C160 107.8(4) . .
C132 C170 C160 124.4(4) . .
C127 C172 C137 117.4(4) . .
C127 C172 C188 122.7(4) . .
C137 C172 C188 119.8(4) . .
C178 C173 C122 133.7(4) . .
C178 C173 C192 120.5(4) . .
C192 C173 C122 105.8(4) . .
C173 C178 H178 120.9 . .
C173 C178 C192 118.2(4) . 3_566
C192 C178 H178 120.9 3_566 .
O42 C181 H18A 109.5 . .
O42 C181 H18B 109.5 . .
O42 C181 H18C 109.5 . .
H18A C181 H18B 109.5 . .
H18A C181 H18C 109.5 . .
H18B C181 H18C 109.5 . .
C106 C188 C166 109.0(4) . .
C106 C188 C172 108.9(4) . .
C106 C188 C195 109.4(4) . .
C166 C188 C172 110.3(4) . .
C166 C188 C195 107.0(4) . .
C172 C188 C195 112.2(4) . .
C173 C192 C200 108.7(4) . .
C178 C192 C173 121.3(4) 3_566 .
C178 C192 C200 129.9(4) 3_566 .
C188 C195 H19A 109.5 . .
C188 C195 H19B 109.5 . .
C188 C195 H19C 109.5 . .
H19A C195 H19B 109.5 . .
H19A C195 H19C 109.5 . .
H19B C195 H19C 109.5 . .
C91 C200 C192 108.7(4) . .
C91 C200 H200 125.6 . .
C192 C200 H200 125.6 . .
Cl2 C48 Cl6 108.7(3) . .
Cl2 C48 D48 108.2 . .
Cl6 C48 D48 108.2 . .
Cl12 C48 Cl2 113.2(4) . .
Cl12 C48 Cl6 110.4(3) . .
Cl12 C48 D48 108.2 . .
O39 C4 H4A 109.5 . .
O39 C4 H4B 109.5 . .
O39 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
Cl1 C5 Cl3 111.2 . .
Cl1 C5 D5 107.7 . .
Cl3 C5 D5 107.7 . .
Cl4 C5 Cl1 111.2 . .
Cl4 C5 Cl3 111.1 . .
Cl4 C5 D5 107.7 . .
Cl5 C1 Cl8 111.2 . .
Cl5 C1 D1 107.6 . .
Cl7 C1 Cl5 111.3 . .
Cl7 C1 Cl8 111.3 . .
Cl7 C1 D1 107.7 . .
Cl8 C1 D1 107.6 . .
Cl9 C2 Cl10 111.1 . .
Cl9 C2 D2 107.7 . .
Cl10 C2 D2 107.8 . .
Cl11 C2 Cl9 111.2 . .
Cl11 C2 Cl10 111.2 . .
Cl11 C2 D2 107.6 . .
Cl13 C3 D3 107.6 . .
Cl14 C3 Cl13 111.2 . .
Cl14 C3 D3 107.6 . .
Cl15 C3 Cl13 111.3 . .
Cl15 C3 Cl14 111.2 . .
Cl15 C3 D3 107.7 . .
Cl16 C6 Cl17 108.0(5) . .
Cl16 C6 Cl18 112.2(5) . .
Cl16 C6 D6 111.2(14) . .
Cl17 C6 D6 109.0(14) . .
Cl18 C6 Cl17 107.0(4) . .
Cl18 C6 D6 109.4(14) . .
Cl16 C7 Cl1A 111.6(11) . .
Cl16 C7 Cl1B 111.9(10) . .
Cl16 C7 D7 110.0(17) . .
Cl1A C7 Cl1B 107.5(11) . .
Cl1A C7 D7 109.6(18) . .
Cl1B C7 D7 106.1(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O39 C109 1.359(5) .
O39 C4 1.422(6) .
O42 C144 1.365(6) .
O42 C181 1.430(6) .
C50 H50A 0.9800 .
C50 H50B 0.9800 .
C50 H50C 0.9800 .
C50 C52 1.538(7) .
C52 C67 1.515(7) .
C52 C78 1.517(7) .
C52 C112 1.544(7) .
C57 H57A 0.9900 .
C57 H57B 0.9900 .
C57 C144 1.393(7) .
C57 C155 1.382(7) .
C67 H67A 0.9800 .
C67 H67B 0.9800 .
C67 H67C 0.9800 .
C74 H74 0.9500 .
C74 C120 1.393(7) .
C74 C133 1.383(7) .
C76 H76 0.9500 .
C76 C83 1.393(6) .
C76 C99 1.399(6) .
C78 H78A 0.9800 .
C78 H78B 0.9800 .
C78 H78C 0.9800 .
C82 H82 0.9500 .
C82 C83 1.385(7) .
C82 C108 1.381(6) .
C83 C147 1.471(6) .
C91 C122 1.468(6) .
C91 C147 1.460(6) .
C91 C200 1.350(6) .
C99 H99 0.9500 .
C99 C109 1.382(7) .
C106 H10A 0.9800 .
C106 H10B 0.9800 .
C106 H10C 0.9800 .
C106 C188 1.526(8) .
C108 H108 0.9500 .
C108 C109 1.398(6) .
C112 C127 1.383(7) .
C112 C157 1.392(6) .
C120 C155 1.388(6) .
C120 C160 1.473(6) .
C122 C170 1.357(6) .
C122 C173 1.463(6) .
C127 H127 0.9500 .
C127 C172 1.388(7) .
C132 C137 1.392(6) .
C132 C157 1.400(6) .
C132 C170 1.474(6) .
C133 H133 0.9500 .
C133 C144 1.386(7) .
C137 H137 0.9500 .
C137 C172 1.393(6) .
C147 C160 1.382(6) .
C155 H155 0.9500 .
C157 H157 0.9500 .
C160 C170 1.501(6) .
C166 H16A 0.9800 .
C166 H16B 0.9800 .
C166 H16C 0.9800 .
C166 C188 1.527(7) .
C172 C188 1.527(6) .
C173 C178 1.383(6) .
C173 C192 1.428(6) .
C178 H178 0.9500 .
C178 C192 1.389(7) 3_566
C181 H18A 0.9800 .
C181 H18B 0.9800 .
C181 H18C 0.9800 .
C188 C195 1.541(7) .
C192 C178 1.389(7) 3_566
C192 C200 1.472(6) .
C195 H19A 0.9800 .
C195 H19B 0.9800 .
C195 H19C 0.9800 .
C200 H200 0.9500 .
Cl2 C48 1.742(5) .
Cl6 C48 1.780(6) .
Cl12 C48 1.719(6) .
C48 D48 1.0000 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
Cl1 C5 1.7765 .
Cl3 C5 1.7766 .
Cl4 C5 1.7757 .
C5 D5 1.0904 .
Cl5 C1 1.7762 .
Cl7 C1 1.7745 .
Cl8 C1 1.7771 .
C1 D1 1.0911 .
Cl9 C2 1.7759 .
Cl10 C2 1.7760 .
Cl11 C2 1.7750 .
C2 D2 1.0900 .
Cl13 C3 1.7770 .
Cl14 C3 1.7761 .
Cl15 C3 1.7754 .
C3 D3 1.0909 .
Cl16 C6 1.742(9) .
Cl16 C7 1.740(17) .
Cl17 C6 1.775(8) .
Cl18 C6 1.753(8) .
C6 D6 1.080(14) .
Cl1A C7 1.745(18) .
Cl1B C7 1.809(17) .
C7 D7 1.090(17) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C50 C52 C112 C127 -59.2(6) . .
C50 C52 C112 C157 122.3(5) . .
C52 C112 C127 C172 -178.6(5) . .
C52 C112 C157 C132 178.6(4) . .
C67 C52 C112 C127 -178.3(5) . .
C67 C52 C112 C157 3.2(7) . .
C74 C120 C155 C57 2.2(7) . .
C74 C120 C160 C147 54.1(7) . .
C74 C120 C160 C170 -124.3(5) . .
C74 C133 C144 O42 -178.7(4) . .
C74 C133 C144 C57 1.2(7) . .
C76 C83 C147 C91 35.0(7) . .
C76 C83 C147 C160 -147.2(5) . .
C76 C99 C109 O39 -178.9(4) . .
C76 C99 C109 C108 1.1(7) . .
C78 C52 C112 C127 60.3(6) . .
C78 C52 C112 C157 -118.2(5) . .
C82 C83 C147 C91 -145.2(5) . .
C82 C83 C147 C160 32.5(7) . .
C82 C108 C109 O39 178.7(4) . .
C82 C108 C109 C99 -1.2(7) . .
C83 C76 C99 C109 0.0(7) . .
C83 C82 C108 C109 0.3(7) . .
C83 C147 C160 C120 3.7(8) . .
C83 C147 C160 C170 -177.7(4) . .
C91 C122 C170 C132 176.7(4) . .
C91 C122 C170 C160 -2.1(5) . .
C91 C122 C173 C178 -178.7(5) . .
C91 C122 C173 C192 1.2(5) . .
C91 C147 C160 C120 -178.2(4) . .
C91 C147 C160 C170 0.4(5) . .
C99 C76 C83 C82 -0.9(7) . .
C99 C76 C83 C147 178.9(4) . .
C108 C82 C83 C76 0.7(7) . .
C108 C82 C83 C147 -179.1(4) . .
C112 C127 C172 C137 -0.5(7) . .
C112 C127 C172 C188 -176.2(5) . .
C120 C74 C133 C144 1.0(7) . .
C120 C160 C170 C122 179.8(4) . .
C120 C160 C170 C132 1.0(7) . .
C122 C91 C147 C83 176.5(4) . .
C122 C91 C147 C160 -1.7(5) . .
C122 C91 C200 C192 1.1(5) . .
C122 C173 C178 C192 178.2(5) . 3_566
C122 C173 C192 C178 -178.2(4) . 3_566
C122 C173 C192 C200 -0.5(5) . .
C127 C112 C157 C132 0.1(7) . .
C127 C172 C188 C106 105.1(5) . .
C127 C172 C188 C166 -135.3(5) . .
C127 C172 C188 C195 -16.1(7) . .
C132 C137 C172 C127 0.9(7) . .
C132 C137 C172 C188 176.8(4) . .
C133 C74 C120 C155 -2.7(6) . .
C133 C74 C120 C160 176.6(4) . .
C137 C132 C157 C112 0.3(7) . .
C137 C132 C170 C122 -136.0(5) . .
C137 C132 C170 C160 42.6(7) . .
C137 C172 C188 C106 -70.5(6) . .
C137 C172 C188 C166 49.1(6) . .
C137 C172 C188 C195 168.3(5) . .
C144 C57 C155 C120 0.0(7) . .
C147 C91 C122 C170 2.4(5) . .
C147 C91 C122 C173 176.9(4) . .
C147 C91 C200 C192 -176.3(6) . .
C147 C160 C170 C122 1.1(5) . .
C147 C160 C170 C132 -177.8(4) . .
C155 C57 C144 O42 178.3(4) . .
C155 C57 C144 C133 -1.7(7) . .
C155 C120 C160 C147 -126.5(5) . .
C155 C120 C160 C170 55.0(6) . .
C157 C112 C127 C172 0.0(8) . .
C157 C132 C137 C172 -0.9(7) . .
C157 C132 C170 C122 44.2(7) . .
C157 C132 C170 C160 -137.2(5) . .
C160 C120 C155 C57 -177.1(4) . .
C170 C122 C173 C178 -7.4(11) . .
C170 C122 C173 C192 172.4(7) . .
C170 C132 C137 C172 179.3(4) . .
C170 C132 C157 C112 -179.9(4) . .
C173 C122 C170 C132 5.5(10) . .
C173 C122 C170 C160 -173.3(6) . .
C173 C192 C200 C91 -0.4(5) . .
C178 C173 C192 C178 1.7(8) . 3_566
C178 C173 C192 C200 179.3(4) . .
C178 C192 C200 C91 177.0(5) 3_566 .
C181 O42 C144 C57 -8.5(7) . .
C181 O42 C144 C133 171.5(4) . .
C192 C173 C178 C192 -1.6(8) . 3_566
C200 C91 C122 C170 -176.0(4) . .
C200 C91 C122 C173 -1.5(5) . .
C200 C91 C147 C83 -6.1(10) . .
C200 C91 C147 C160 175.8(7) . .
C4 O39 C109 C99 -2.0(7) . .
C4 O39 C109 C108 178.0(4) . .
C6 Cl16 C7 Cl1A -73.2(13) . .
C6 Cl16 C7 Cl1B 47.4(9) . .
C7 Cl16 C6 Cl17 -130.2(13) . .
C7 Cl16 C6 Cl18 -12.5(11) . .
