#------------------------------------------------------------------------------
#$Date: 2024-04-05 02:06:16 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290884 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/82/7248272.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_7248272
loop_
_publ_author_name
'Barton, Benita'
'Caira, Mino R.'
'Senekal, Ulrich'
'Hosten, Eric C.'
_publ_section_title
;
 Host compounds based on the rigid 9,10-dihydro-9,10-ethanoanthracene
 framework: selectivity behaviour in mixed isomeric dichlorobenzenes
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              1862
_journal_page_last               1875
_journal_paper_doi               10.1039/D4CE00113C
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C42 H34 O2, C6 H4 Cl2'
_chemical_formula_sum            'C48 H38 Cl2 O2'
_chemical_formula_weight         717.68
_chemical_melting_point          'decomp. (guest loss) onset 333 K'
_chemical_name_common            none
_chemical_name_systematic
'trans-alpha, alpha, alpha',alpha'-tetraphenyl-9,10-dihydro-9,10-ethano-anthracene-11,12-dimethanol 1,2-dichlorobenzene clathrate'
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-01-29 deposited with the CCDC.	2024-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.752(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4249(18)
_cell_length_b                   11.7971(18)
_cell_length_c                   24.951(4)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.38
_cell_volume                     3638.8(10)
_computing_cell_refinement
'SAINT V8.40A, Bruker AXS Inc.: Madison (WI), USA.'
_computing_data_collection       'Apex3 v2019.1-0, Bruker (2019).'
_computing_data_reduction
'SAINT V8.40A, Bruker AXS Inc.: Madison (WI), USA.'
_computing_molecular_graphics
'POV-Ray in interface X-Seed (LJ Barbour, 1999)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-Version 2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean n/a
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE SCXRD diffractometer'
_diffrn_measurement_method       'omega-and phi-scans, width 0.5 deg.'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1398
_diffrn_reflns_av_unetI/netI     0.1076
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            77693
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_min         1.641
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.3600
_exptl_absorpt_correction_T_min  0.2851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       plate
_exptl_crystal_F_000             1504
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,2-dichlorobenzene'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         9059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0578P)²+1.4386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6691
_reflns_number_total             9059
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00113c2.cif
_cod_data_source_block           3ODICL
_cod_depositor_comments
'Adding full bibliography for 7248272--7248274.cif.'
_cod_original_cell_volume        3638.9(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7248272
_shelx_shelxl_version_number     2018/3
_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   0.941
_shelx_estimated_absorpt_t_max   0.985
_exptl_absorpt_special_details   'appended - end of file'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.25252(14) 0.16597(16) 0.55918(7) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.31556(15) 0.21085(18) 0.52147(7) 0.0293(4) Uani 1 1 d . . . . .
H2 H 0.377526 0.171269 0.512035 0.035 Uiso 1 1 calc R U . . .
C3 C 0.28660(17) 0.31521(19) 0.49753(8) 0.0342(5) Uani 1 1 d . . . . .
H3 H 0.328437 0.346028 0.471202 0.041 Uiso 1 1 calc R U . . .
C4 C 0.19743(17) 0.37381(18) 0.51196(8) 0.0333(4) Uani 1 1 d . . . . .
H4 H 0.178270 0.444409 0.495344 0.040 Uiso 1 1 calc R U . . .
C5 C 0.13534(16) 0.32981(16) 0.55082(7) 0.0273(4) Uani 1 1 d . . . . .
H5 H 0.075093 0.370946 0.561243 0.033 Uiso 1 1 calc R U . . .
C6 C 0.16250(14) 0.22578(15) 0.57396(7) 0.0221(3) Uani 1 1 d . . . . .
C7 C 0.07208(14) 0.04875(15) 0.58889(7) 0.0221(3) Uani 1 1 d . . . . .
C8 C -0.03061(14) 0.00130(17) 0.57931(7) 0.0261(4) Uani 1 1 d . . . . .
H8 H -0.092430 0.041711 0.588328 0.031 Uiso 1 1 calc R U . . .
C9 C -0.04155(16) -0.10613(17) 0.55634(8) 0.0304(4) Uani 1 1 d . . . . .
H9 H -0.111320 -0.139217 0.549727 0.037 Uiso 1 1 calc R U . . .
C10 C 0.04828(16) -0.16517(17) 0.54304(8) 0.0307(4) Uani 1 1 d . . . . .
H10 H 0.039570 -0.238686 0.527675 0.037 Uiso 1 1 calc R U . . .
C11 C 0.15150(15) -0.11795(16) 0.55195(7) 0.0264(4) Uani 1 1 d . . . . .
H11 H 0.212978 -0.158192 0.542370 0.032 Uiso 1 1 calc R U . . .
C12 C 0.16262(14) -0.01110(15) 0.57506(7) 0.0217(3) Uani 1 1 d . . . . .
C13 C 0.26770(14) 0.05305(15) 0.58777(7) 0.0220(3) Uani 1 1 d . . . . .
H13 H 0.330310 0.010272 0.575562 0.026 Uiso 1 1 calc R U . . .
C14 C 0.28222(13) 0.07350(14) 0.65073(7) 0.0201(3) Uani 1 1 d . . . . .
H14 H 0.281294 -0.002443 0.668486 0.024 Uiso 1 1 calc R U . . .
C15 C 0.18074(13) 0.14126(14) 0.66657(6) 0.0191(3) Uani 1 1 d . . . . .
H15 H 0.206395 0.216589 0.681124 0.023 Uiso 1 1 calc R U . . .
C16 C 0.10128(14) 0.16282(15) 0.61406(7) 0.0215(3) Uani 1 1 d . . . . .
H16 H 0.035406 0.205496 0.622343 0.026 Uiso 1 1 calc R U . . .
C17 C 0.39590(13) 0.12832(14) 0.66781(7) 0.0208(3) Uani 1 1 d . . . . .
O18 O 0.39615(10) 0.24475(10) 0.65241(5) 0.0250(3) Uani 1 1 d . . . . .
H18 H 0.376147 0.250456 0.619354 0.030 Uiso 1 1 calc R U . . .
C19 C 0.48530(14) 0.06172(16) 0.64229(7) 0.0236(4) Uani 1 1 d . . . . .
C20 C 0.49374(17) -0.05587(18) 0.64782(8) 0.0331(4) Uani 1 1 d . . . . .
H20 H 0.442857 -0.095986 0.666596 0.040 Uiso 1 1 calc R U . . .
C21 C 0.57586(19) -0.1145(2) 0.62610(10) 0.0425(5) Uani 1 1 d . . . . .
H21 H 0.580834 -0.194477 0.630047 0.051 Uiso 1 1 calc R U . . .
C22 C 0.65068(19) -0.0570(2) 0.59869(9) 0.0464(6) Uani 1 1 d . . . . .
H22 H 0.707139 -0.097194 0.584012 0.056 Uiso 1 1 calc R U . . .
C23 C 0.64261(18) 0.0585(2) 0.59290(10) 0.0457(6) Uani 1 1 d . . . . .
H23 H 0.693387 0.097996 0.573802 0.055 Uiso 1 1 calc R U . . .
C24 C 0.56093(16) 0.11823(19) 0.61467(8) 0.0342(4) Uani 1 1 d . . . . .
H24 H 0.556776 0.198235 0.610653 0.041 Uiso 1 1 calc R U . . .
C25 C 0.43208(13) 0.12825(15) 0.72853(7) 0.0212(3) Uani 1 1 d . . . . .
C26 C 0.49260(15) 0.21932(16) 0.75134(8) 0.0273(4) Uani 1 1 d . . . . .
H26 H 0.504738 0.283793 0.729940 0.033 Uiso 1 1 calc R U . . .
C27 C 0.53516(17) 0.21633(18) 0.80505(8) 0.0343(5) Uani 1 1 d . . . . .
H27 H 0.575731 0.278940 0.820085 0.041 Uiso 1 1 calc R U . . .
C28 C 0.51885(17) 0.12294(19) 0.83670(8) 0.0346(5) Uani 1 1 d . . . . .
H28 H 0.547820 0.121266 0.873405 0.042 Uiso 1 1 calc R U . . .
C29 C 0.45997(16) 0.03195(17) 0.81448(8) 0.0308(4) Uani 1 1 d . . . . .
H29 H 0.448836 -0.032607 0.836003 0.037 Uiso 1 1 calc R U . . .
C30 C 0.41713(15) 0.03431(16) 0.76103(7) 0.0260(4) Uani 1 1 d . . . . .
H30 H 0.377028 -0.028873 0.746281 0.031 Uiso 1 1 calc R U . . .
C31 C 0.12003(14) 0.08026(14) 0.71101(7) 0.0207(3) Uani 1 1 d . . . . .
O32 O 0.11574(11) -0.03932(10) 0.70123(5) 0.0251(3) Uani 1 1 d . . . . .
H32 H 0.087914 -0.051520 0.669675 0.030 Uiso 1 1 calc R U . . .
C33 C 0.00421(14) 0.12692(16) 0.71336(7) 0.0226(4) Uani 1 1 d . . . . .
C34 C -0.01318(15) 0.24195(17) 0.72176(8) 0.0282(4) Uani 1 1 d . . . . .
H34 H 0.046828 0.292257 0.724567 0.034 Uiso 1 1 calc R U . . .
C35 C -0.11576(17) 0.2848(2) 0.72611(9) 0.0369(5) Uani 1 1 d . . . . .
H35 H -0.125359 0.363498 0.732281 0.044 Uiso 1 1 calc R U . . .
C36 C -0.20425(17) 0.2129(2) 0.72146(9) 0.0406(5) Uani 1 1 d . . . . .
H36 H -0.274920 0.242023 0.723763 0.049 Uiso 1 1 calc R U . . .
C37 C -0.18892(16) 0.0984(2) 0.71344(9) 0.0390(5) Uani 1 1 d . . . . .
H37 H -0.249436 0.048807 0.710171 0.047 Uiso 1 1 calc R U . . .
C38 C -0.08571(15) 0.05522(18) 0.71011(8) 0.0297(4) Uani 1 1 d . . . . .
H38 H -0.076210 -0.023985 0.705568 0.036 Uiso 1 1 calc R U . . .
C39 C 0.17421(13) 0.09383(15) 0.76857(7) 0.0211(3) Uani 1 1 d . . . . .
C40 C 0.17006(15) 0.00407(16) 0.80478(7) 0.0266(4) Uani 1 1 d . . . . .
H40 H 0.140374 -0.066653 0.792557 0.032 Uiso 1 1 calc R U . . .
C41 C 0.20903(16) 0.01748(19) 0.85851(8) 0.0330(4) Uani 1 1 d . . . . .
H41 H 0.206100 -0.044295 0.882740 0.040 Uiso 1 1 calc R U . . .
C42 C 0.25206(16) 0.11990(19) 0.87708(8) 0.0340(5) Uani 1 1 d . . . . .
H42 H 0.277829 0.128841 0.913984 0.041 Uiso 1 1 calc R U . . .
C43 C 0.25736(16) 0.20945(17) 0.84149(8) 0.0296(4) Uani 1 1 d . . . . .
H43 H 0.286970 0.279977 0.854036 0.036 Uiso 1 1 calc R U . . .
C44 C 0.21953(15) 0.19644(15) 0.78757(7) 0.0249(4) Uani 1 1 d . . . . .
H44 H 0.224497 0.257908 0.763339 0.030 Uiso 1 1 calc R U . . .
C45 C 0.62303(16) 0.38928(18) 0.55244(8) 0.0329(4) Uani 1 1 d . . . . .
C46 C 0.72530(16) 0.39448(19) 0.58030(9) 0.0357(5) Uani 1 1 d . . . . .
C47 C 0.74379(19) 0.4637(2) 0.62479(10) 0.0457(6) Uani 1 1 d . . . . .
H47 H 0.813784 0.467035 0.643929 0.055 Uiso 1 1 calc R U . . .
C48 C 0.6603(2) 0.5286(2) 0.64166(10) 0.0507(6) Uani 1 1 d . . . . .
H48 H 0.673250 0.576909 0.672080 0.061 Uiso 1 1 calc R U . . .
C49 C 0.5582(2) 0.5227(2) 0.61406(10) 0.0461(6) Uani 1 1 d . . . . .
H49 H 0.500793 0.566523 0.625765 0.055 Uiso 1 1 calc R U . . .
C50 C 0.53949(17) 0.4535(2) 0.56962(9) 0.0375(5) Uani 1 1 d . . . . .
H50 H 0.469293 0.449702 0.550731 0.045 Uiso 1 1 calc R U . . .
Cl51 Cl 0.59848(5) 0.30423(5) 0.49609(2) 0.04582(17) Uani 1 1 d . . . . .
Cl52 Cl 0.83145(5) 0.31538(6) 0.55971(3) 0.0564(2) Uani 1 1 d . . . . .
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'
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'
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
_geom_angle_publ_flag
C2 C1 C6 120.35(17) . . ?
C2 C1 C13 127.07(17) . . ?
C6 C1 C13 112.57(15) . . ?
C1 C2 C3 119.10(19) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 120.45(18) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.45(19) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.36(19) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.27(17) . . ?
C5 C6 C16 126.47(17) . . ?
C1 C6 C16 113.23(15) . . ?
C8 C7 C12 120.01(17) . . ?
C8 C7 C16 127.32(16) . . ?
C12 C7 C16 112.67(15) . . ?
C9 C8 C7 119.14(18) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 120.61(17) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.75(18) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 118.72(18) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C7 120.77(16) . . ?
C11 C12 C13 126.06(16) . . ?
C7 C12 C13 113.17(15) . . ?
C1 C13 C12 106.07(14) . . ?
C1 C13 C14 109.28(14) . . ?
C12 C13 C14 107.11(14) . . ?
C1 C13 H13 111.4 . . ?
C12 C13 H13 111.4 . . ?
C14 C13 H13 111.4 . . ?
C17 C14 C15 116.27(14) . . ?
C17 C14 C13 109.98(14) . . ?
C15 C14 C13 108.17(13) . . ?
C17 C14 H14 107.3 . . ?
C15 C14 H14 107.3 . . ?
C13 C14 H14 107.3 . . ?
C31 C15 C14 113.33(13) . . ?
C31 C15 C16 110.70(13) . . ?
C14 C15 C16 108.83(13) . . ?
C31 C15 H15 107.9 . . ?
C14 C15 H15 107.9 . . ?
C16 C15 H15 107.9 . . ?
C6 C16 C7 106.13(14) . . ?
C6 C16 C15 108.30(13) . . ?
C7 C16 C15 107.74(13) . . ?
C6 C16 H16 111.5 . . ?
C7 C16 H16 111.5 . . ?
C15 C16 H16 111.5 . . ?
O18 C17 C25 104.94(13) . . ?
O18 C17 C19 110.90(14) . . ?
C25 C17 C19 104.73(13) . . ?
O18 C17 C14 110.43(13) . . ?
C25 C17 C14 115.66(14) . . ?
C19 C17 C14 109.97(14) . . ?
C17 O18 H18 109.5 . . ?
C24 C19 C20 118.52(18) . . ?
C24 C19 C17 120.59(17) . . ?
C20 C19 C17 120.86(17) . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.5(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.7(2) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C19 C24 C23 120.5(2) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C30 C25 C26 118.06(16) . . ?
C30 C25 C17 122.02(16) . . ?
C26 C25 C17 119.53(16) . . ?
C27 C26 C25 120.63(18) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C28 C27 C26 120.49(19) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 119.43(18) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C28 C29 C30 120.45(19) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 120.94(18) . . ?
C29 C30 H30 119.5 . . ?
C25 C30 H30 119.5 . . ?
O32 C31 C39 105.54(13) . . ?
O32 C31 C33 109.76(14) . . ?
C39 C31 C33 104.49(13) . . ?
O32 C31 C15 110.02(13) . . ?
C39 C31 C15 114.55(14) . . ?
C33 C31 C15 112.14(13) . . ?
C31 O32 H32 109.5 . . ?
C34 C33 C38 117.60(17) . . ?
C34 C33 C31 120.73(15) . . ?
C38 C33 C31 121.59(17) . . ?
C35 C34 C33 121.68(19) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C36 C35 C34 119.9(2) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C37 C36 C35 119.45(19) . . ?
C37 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C36 C37 C38 120.6(2) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C37 C38 C33 120.8(2) . . ?
C37 C38 H38 119.6 . . ?
C33 C38 H38 119.6 . . ?
C40 C39 C44 118.51(16) . . ?
C40 C39 C31 119.08(16) . . ?
C44 C39 C31 122.17(15) . . ?
C41 C40 C39 120.43(18) . . ?
C41 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
C42 C41 C40 120.61(18) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C41 C42 C43 119.55(18) . . ?
C41 C42 H42 120.2 . . ?
C43 C42 H42 120.2 . . ?
C42 C43 C44 120.23(19) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C43 C44 C39 120.66(18) . . ?
C43 C44 H44 119.7 . . ?
C39 C44 H44 119.7 . . ?
C50 C45 C46 119.8(2) . . ?
C50 C45 Cl51 119.45(16) . . ?
C46 C45 Cl51 120.73(17) . . ?
C47 C46 C45 120.0(2) . . ?
C47 C46 Cl52 119.12(17) . . ?
C45 C46 Cl52 120.89(18) . . ?
C46 C47 C48 120.1(2) . . ?
C46 C47 H47 120.0 . . ?
C48 C47 H47 120.0 . . ?
C49 C48 C47 119.8(2) . . ?
C49 C48 H48 120.1 . . ?
C47 C48 H48 120.1 . . ?
C50 C49 C48 120.2(2) . . ?
C50 C49 H49 119.9 . . ?
C48 C49 H49 119.9 . . ?
C49 C50 C45 120.1(2) . . ?
C49 C50 H50 120.0 . . ?
C45 C50 H50 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.388(3) . ?
C1 C6 1.403(3) . ?
C1 C13 1.514(2) . ?
C2 C3 1.400(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 C16 1.511(2) . ?
C7 C8 1.392(2) . ?
C7 C12 1.400(2) . ?
C7 C16 1.514(2) . ?
C8 C9 1.392(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.515(2) . ?
C13 C14 1.582(2) . ?
C13 H13 1.0000 . ?
C14 C17 1.573(2) . ?
C14 C15 1.576(2) . ?
C14 H14 1.0000 . ?
C15 C31 1.576(2) . ?
C15 C16 1.580(2) . ?
C15 H15 1.0000 . ?
C16 H16 1.0000 . ?
C17 O18 1.426(2) . ?
C17 C25 1.536(2) . ?
C17 C19 1.549(2) . ?
O18 H18 0.8400 . ?
C19 C24 1.390(3) . ?
C19 C20 1.397(3) . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.373(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C30 1.397(3) . ?
C25 C26 1.399(3) . ?
C26 C27 1.391(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.382(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 O32 1.432(2) . ?
C31 C39 1.532(2) . ?
C31 C33 1.547(2) . ?
O32 H32 0.8400 . ?
C33 C34 1.393(3) . ?
C33 C38 1.397(3) . ?
C34 C35 1.386(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.381(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.390(3) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C40 1.396(2) . ?
C39 C44 1.398(3) . ?
C40 C41 1.388(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.382(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.386(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.389(3) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 C50 1.387(3) . ?
C45 C46 1.387(3) . ?
C45 Cl51 1.729(2) . ?
C46 C47 1.379(3) . ?
C46 Cl52 1.735(2) . ?
C47 C48 1.388(4) . ?
C47 H47 0.9500 . ?
C48 C49 1.384(4) . ?
C48 H48 0.9500 . ?
C49 C50 1.378(3) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C14 H14 O32 1.00 2.33 2.857(2) 111.9 . yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.5(3) . . . . ?
C13 C1 C2 C3 177.45(17) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C16 -176.42(17) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C13 C1 C6 C5 -178.67(15) . . . . ?
C2 C1 C6 C16 178.16(15) . . . . ?
C13 C1 C6 C16 -0.9(2) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
C16 C7 C8 C9 -179.06(17) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C7 -0.4(3) . . . . ?
C10 C11 C12 C13 179.85(17) . . . . ?
C8 C7 C12 C11 -0.2(3) . . . . ?
C16 C7 C12 C11 179.40(15) . . . . ?
C8 C7 C12 C13 179.52(15) . . . . ?
C16 C7 C12 C13 -0.9(2) . . . . ?
C2 C1 C13 C12 -122.75(18) . . . . ?
C6 C1 C13 C12 56.23(18) . . . . ?
C2 C1 C13 C14 122.09(18) . . . . ?
C6 C1 C13 C14 -58.92(18) . . . . ?
C11 C12 C13 C1 124.34(18) . . . . ?
C7 C12 C13 C1 -55.39(18) . . . . ?
C11 C12 C13 C14 -119.03(18) . . . . ?
C7 C12 C13 C14 61.23(18) . . . . ?
C1 C13 C14 C17 -71.54(17) . . . . ?
C12 C13 C14 C17 173.97(13) . . . . ?
C1 C13 C14 C15 56.41(17) . . . . ?
C12 C13 C14 C15 -58.08(17) . . . . ?
C17 C14 C15 C31 -111.51(16) . . . . ?
C13 C14 C15 C31 124.22(15) . . . . ?
C17 C14 C15 C16 124.86(15) . . . . ?
C13 C14 C15 C16 0.58(18) . . . . ?
C5 C6 C16 C7 122.23(18) . . . . ?
C1 C6 C16 C7 -55.38(18) . . . . ?
C5 C6 C16 C15 -122.32(18) . . . . ?
C1 C6 C16 C15 60.07(18) . . . . ?
C8 C7 C16 C6 -124.16(18) . . . . ?
C12 C7 C16 C6 56.24(18) . . . . ?
C8 C7 C16 C15 120.01(18) . . . . ?
C12 C7 C16 C15 -59.59(18) . . . . ?
C31 C15 C16 C6 177.58(13) . . . . ?
C14 C15 C16 C6 -57.23(17) . . . . ?
C31 C15 C16 C7 -68.02(17) . . . . ?
C14 C15 C16 C7 57.17(17) . . . . ?
C15 C14 C17 O18 -48.94(19) . . . . ?
C13 C14 C17 O18 74.40(17) . . . . ?
C15 C14 C17 C25 70.01(18) . . . . ?
C13 C14 C17 C25 -166.65(14) . . . . ?
C15 C14 C17 C19 -171.65(14) . . . . ?
C13 C14 C17 C19 -48.31(18) . . . . ?
O18 C17 C19 C24 7.8(2) . . . . ?
C25 C17 C19 C24 -104.90(18) . . . . ?
C14 C17 C19 C24 130.22(17) . . . . ?
O18 C17 C19 C20 -174.12(16) . . . . ?
C25 C17 C19 C20 73.2(2) . . . . ?
C14 C17 C19 C20 -51.7(2) . . . . ?
C24 C19 C20 C21 -0.1(3) . . . . ?
C17 C19 C20 C21 -178.21(18) . . . . ?
C19 C20 C21 C22 0.1(3) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C24 0.6(4) . . . . ?
C20 C19 C24 C23 0.3(3) . . . . ?
C17 C19 C24 C23 178.48(18) . . . . ?
C22 C23 C24 C19 -0.6(3) . . . . ?
O18 C17 C25 C30 164.10(15) . . . . ?
C19 C17 C25 C30 -79.03(19) . . . . ?
C14 C17 C25 C30 42.2(2) . . . . ?
O18 C17 C25 C26 -23.2(2) . . . . ?
C19 C17 C25 C26 93.62(18) . . . . ?
C14 C17 C25 C26 -145.18(16) . . . . ?
C30 C25 C26 C27 -0.8(3) . . . . ?
C17 C25 C26 C27 -173.77(17) . . . . ?
C25 C26 C27 C28 0.4(3) . . . . ?
C26 C27 C28 C29 0.2(3) . . . . ?
C27 C28 C29 C30 -0.3(3) . . . . ?
C28 C29 C30 C25 -0.2(3) . . . . ?
C26 C25 C30 C29 0.7(3) . . . . ?
C17 C25 C30 C29 173.48(16) . . . . ?
C14 C15 C31 O32 -40.00(18) . . . . ?
C16 C15 C31 O32 82.60(16) . . . . ?
C14 C15 C31 C39 78.68(17) . . . . ?
C16 C15 C31 C39 -158.71(14) . . . . ?
C14 C15 C31 C33 -162.45(13) . . . . ?
C16 C15 C31 C33 -39.85(18) . . . . ?
O32 C31 C33 C34 -179.13(15) . . . . ?
C39 C31 C33 C34 68.1(2) . . . . ?
C15 C31 C33 C34 -56.5(2) . . . . ?
O32 C31 C33 C38 4.4(2) . . . . ?
C39 C31 C33 C38 -108.39(18) . . . . ?
C15 C31 C33 C38 126.97(17) . . . . ?
C38 C33 C34 C35 -0.8(3) . . . . ?
C31 C33 C34 C35 -177.43(17) . . . . ?
C33 C34 C35 C36 -0.8(3) . . . . ?
C34 C35 C36 C37 1.1(3) . . . . ?
C35 C36 C37 C38 0.1(3) . . . . ?
C36 C37 C38 C33 -1.7(3) . . . . ?
C34 C33 C38 C37 2.0(3) . . . . ?
C31 C33 C38 C37 178.63(17) . . . . ?
O32 C31 C39 C40 -23.8(2) . . . . ?
C33 C31 C39 C40 91.95(18) . . . . ?
C15 C31 C39 C40 -144.96(16) . . . . ?
O32 C31 C39 C44 161.95(16) . . . . ?
C33 C31 C39 C44 -82.31(19) . . . . ?
C15 C31 C39 C44 40.8(2) . . . . ?
C44 C39 C40 C41 0.8(3) . . . . ?
C31 C39 C40 C41 -173.71(17) . . . . ?
C39 C40 C41 C42 0.3(3) . . . . ?
C40 C41 C42 C43 -0.7(3) . . . . ?
C41 C42 C43 C44 0.1(3) . . . . ?
C42 C43 C44 C39 1.0(3) . . . . ?
C40 C39 C44 C43 -1.4(3) . . . . ?
C31 C39 C44 C43 172.90(17) . . . . ?
C50 C45 C46 C47 -0.3(3) . . . . ?
Cl51 C45 C46 C47 179.26(17) . . . . ?
C50 C45 C46 Cl52 -179.89(16) . . . . ?
Cl51 C45 C46 Cl52 -0.3(3) . . . . ?
C45 C46 C47 C48 -0.2(3) . . . . ?
Cl52 C46 C47 C48 179.37(18) . . . . ?
C46 C47 C48 C49 0.7(4) . . . . ?
C47 C48 C49 C50 -0.6(4) . . . . ?
C48 C49 C50 C45 0.1(4) . . . . ?
C46 C45 C50 C49 0.4(3) . . . . ?
Cl51 C45 C50 C49 -179.19(18) . . . . ?
