#------------------------------------------------------------------------------
#$Date: 2024-04-05 02:06:16 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290884 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/82/7248273.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_7248273
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 H30 Cl4 O2, C6 H4 Cl2'
_chemical_formula_sum            'C48 H34 Cl6 O2'
_chemical_formula_weight         855.45
_chemical_melting_point          331.05
_chemical_name_common
'trans- α,α,α',α'-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-01-31 deposited with the CCDC.	2024-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.807(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.2360(10)
_cell_length_b                   15.6145(8)
_cell_length_c                   24.0913(10)
_cell_measurement_reflns_used    9750
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.61
_cell_volume                     7869.0(7)
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'
_computing_structure_refinement
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9829
_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         28.373
_diffrn_reflns_theta_min         1.607
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  0.745686
_exptl_absorpt_correction_T_min  0.656407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS 2012/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             3520
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: m-dichlorobenzene'
_exptl_crystal_size_max          0.665
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         9829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0489P)²+12.9357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8170
_reflns_number_total             9829
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00113c2.cif
_cod_data_source_block           ma036_tw
_cod_depositor_comments
'Adding full bibliography for 7248272--7248274.cif.'
_cod_original_cell_volume        7869.0(6)
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               7248273
_shelx_shelxl_version_number     2019/3
_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   0.741
_shelx_estimated_absorpt_t_max   0.923
_exptl_absorpt_special_details
;  
Additional spherical absorption correction applied with mu*r =  0.2000
Details of twinning from .abs file
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
Cl1 Cl 0.74704(3) 0.29173(6) 0.59251(3) 0.0479(2) Uani 1 1 d . . . . .
Cl2 Cl 0.69164(3) 0.32806(6) 0.19136(3) 0.04603(19) Uani 1 1 d . . . . .
Cl3 Cl 0.55158(3) 0.40731(5) 0.05262(3) 0.04253(17) Uani 1 1 d . . . . .
Cl4 Cl 0.15012(3) 0.46765(6) -0.00559(3) 0.04320(18) Uani 1 1 d . . . . .
O1 O 0.50304(7) 0.21505(10) 0.31806(7) 0.0230(3) Uani 1 1 d . . . . .
H1A H 0.482507 0.205624 0.338775 0.035 Uiso 1 1 calc R U . . .
O2 O 0.42807(8) 0.51326(10) 0.24345(7) 0.0231(3) Uani 1 1 d . . . . .
H2A H 0.408711 0.519862 0.265569 0.035 Uiso 1 1 calc R U . . .
C1 C 0.53238(10) 0.29775(13) 0.33348(10) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.48051(10) 0.36849(14) 0.32145(9) 0.0194(4) Uani 1 1 d . . . . .
H2 H 0.500401 0.425028 0.320750 0.023 Uiso 1 1 calc R U . . .
C3 C 0.41881(9) 0.35897(14) 0.25871(9) 0.0184(4) Uani 1 1 d . . . . .
H3 H 0.422250 0.303883 0.239200 0.022 Uiso 1 1 calc R U . . .
C4 C 0.41017(10) 0.43299(13) 0.21183(10) 0.0183(4) Uani 1 1 d . . . . .
C5 C 0.45956(11) 0.37110(15) 0.37575(10) 0.0235(4) Uani 1 1 d . . . . .
H5 H 0.497133 0.378374 0.416747 0.028 Uiso 1 1 calc R U . . .
C6 C 0.35855(10) 0.35268(15) 0.27280(10) 0.0227(4) Uani 1 1 d . . . . .
H6 H 0.318137 0.345310 0.234181 0.027 Uiso 1 1 calc R U . . .
C11 C 0.58409(10) 0.29793(15) 0.40080(10) 0.0221(4) Uani 1 1 d . . . . .
C12 C 0.60480(13) 0.22148(18) 0.43229(12) 0.0356(6) Uani 1 1 d . . . . .
H12 H 0.584968 0.169298 0.413266 0.043 Uiso 1 1 calc R U . . .
C13 C 0.65432(14) 0.2204(2) 0.49149(13) 0.0454(7) Uani 1 1 d . . . . .
H13 H 0.667835 0.167567 0.512848 0.054 Uiso 1 1 calc R U . . .
C14 C 0.68371(11) 0.2949(2) 0.51915(11) 0.0333(6) Uani 1 1 d . . . . .
C15 C 0.66374(12) 0.37184(19) 0.48920(11) 0.0340(6) Uani 1 1 d . . . . .
H15 H 0.683593 0.423735 0.508781 0.041 Uiso 1 1 calc R U . . .
C16 C 0.61415(12) 0.37298(16) 0.42988(11) 0.0294(5) Uani 1 1 d . . . . .
H16 H 0.600646 0.426066 0.408925 0.035 Uiso 1 1 calc R U . . .
C21 C 0.56968(10) 0.30740(14) 0.29463(10) 0.0204(4) Uani 1 1 d . . . . .
C22 C 0.58874(12) 0.23493(16) 0.27370(12) 0.0276(5) Uani 1 1 d . . . . .
H22 H 0.575494 0.180118 0.280814 0.033 Uiso 1 1 calc R U . . .
C23 C 0.62683(13) 0.24084(17) 0.24255(12) 0.0326(5) Uani 1 1 d . . . . .
H23 H 0.639529 0.190711 0.228443 0.039 Uiso 1 1 calc R U . . .
C24 C 0.64588(11) 0.32070(18) 0.23245(11) 0.0292(5) Uani 1 1 d . . . . .
C25 C 0.62887(11) 0.39370(17) 0.25356(11) 0.0289(5) Uani 1 1 d . . . . .
H25 H 0.642998 0.448216 0.247005 0.035 Uiso 1 1 calc R U . . .
C26 C 0.59077(11) 0.38685(15) 0.28460(11) 0.0244(4) Uani 1 1 d . . . . .
H26 H 0.578901 0.437185 0.299223 0.029 Uiso 1 1 calc R U . . .
C31 C 0.45115(10) 0.42345(15) 0.17654(10) 0.0205(4) Uani 1 1 d . . . . .
C32 C 0.46169(11) 0.34484(15) 0.15542(10) 0.0232(4) Uani 1 1 d . . . . .
H32 H 0.447370 0.293917 0.167043 0.028 Uiso 1 1 calc R U . . .
C33 C 0.49278(11) 0.33938(16) 0.11763(11) 0.0273(5) Uani 1 1 d . . . . .
H33 H 0.499931 0.285191 0.103814 0.033 Uiso 1 1 calc R U . . .
C34 C 0.51320(11) 0.41344(17) 0.10030(11) 0.0269(5) Uani 1 1 d . . . . .
C35 C 0.50287(12) 0.49234(17) 0.12004(11) 0.0288(5) Uani 1 1 d . . . . .
H35 H 0.516831 0.543104 0.107856 0.035 Uiso 1 1 calc R U . . .
C36 C 0.47185(11) 0.49690(15) 0.15791(11) 0.0249(4) Uani 1 1 d . . . . .
H36 H 0.464619 0.551304 0.171369 0.030 Uiso 1 1 calc R U . . .
C41 C 0.34156(10) 0.43917(15) 0.16014(10) 0.0216(4) Uani 1 1 d . . . . .
C42 C 0.31095(12) 0.51807(17) 0.14428(12) 0.0330(5) Uani 1 1 d . . . . .
H42 H 0.331049 0.567082 0.168251 0.040 Uiso 1 1 calc R U . . .
C43 C 0.25166(13) 0.5267(2) 0.09419(13) 0.0401(6) Uani 1 1 d . . . . .
H43 H 0.231250 0.581024 0.084256 0.048 Uiso 1 1 calc R U . . .
C44 C 0.22273(11) 0.45629(19) 0.05911(10) 0.0312(5) Uani 1 1 d . . . . .
C45 C 0.25112(11) 0.37633(18) 0.07453(11) 0.0304(5) Uani 1 1 d . . . . .
H45 H 0.230300 0.327349 0.050944 0.036 Uiso 1 1 calc R U . . .
C46 C 0.31030(11) 0.36866(16) 0.12481(11) 0.0264(5) Uani 1 1 d . . . . .
H46 H 0.329908 0.313895 0.135307 0.032 Uiso 1 1 calc R U . . .
C51 C 0.42349(11) 0.28915(16) 0.37287(11) 0.0253(5) Uani 1 1 d . . . . .
C52 C 0.36982(11) 0.27842(16) 0.31663(11) 0.0253(5) Uani 1 1 d . . . . .
C53 C 0.33320(12) 0.20476(17) 0.30562(13) 0.0324(5) Uani 1 1 d . . . . .
H53 H 0.297264 0.196453 0.267035 0.039 Uiso 1 1 calc R U . . .
C54 C 0.34965(14) 0.14306(18) 0.35173(15) 0.0394(6) Uani 1 1 d . . . . .
H54 H 0.324672 0.092513 0.344564 0.047 Uiso 1 1 calc R U . . .
C55 C 0.40196(14) 0.15476(19) 0.40776(14) 0.0399(7) Uani 1 1 d . . . . .
H55 H 0.412326 0.112620 0.439093 0.048 Uiso 1 1 calc R U . . .
C56 C 0.43964(13) 0.22783(18) 0.41871(12) 0.0342(6) Uani 1 1 d . . . . .
H56 H 0.475942 0.235527 0.457115 0.041 Uiso 1 1 calc R U . . .
C61 C 0.41221(11) 0.44353(16) 0.36219(11) 0.0252(5) Uani 1 1 d . . . . .
C62 C 0.35689(11) 0.43279(15) 0.30729(11) 0.0240(5) Uani 1 1 d . . . . .
C63 C 0.30862(12) 0.49351(18) 0.28927(12) 0.0316(5) Uani 1 1 d . . . . .
H63 H 0.270830 0.486183 0.252054 0.038 Uiso 1 1 calc R U . . .
C64 C 0.31582(14) 0.56517(18) 0.32593(13) 0.0366(6) Uani 1 1 d . . . . .
H64 H 0.282675 0.606658 0.313922 0.044 Uiso 1 1 calc R U . . .
C65 C 0.37118(14) 0.57632(18) 0.37995(13) 0.0367(6) Uani 1 1 d . . . . .
H65 H 0.375970 0.625847 0.404485 0.044 Uiso 1 1 calc R U . . .
C66 C 0.41996(13) 0.51539(17) 0.39861(12) 0.0309(5) Uani 1 1 d . . . . .
H66 H 0.457863 0.523012 0.435673 0.037 Uiso 1 1 calc R U . . .
Cl71 Cl 0.75364(5) 0.63505(11) 0.38886(6) 0.0974(5) Uani 1 1 d . . . . .
Cl72 Cl 0.58433(6) 0.62168(12) 0.48512(5) 0.1003(5) Uani 1 1 d . . . . .
C71 C 0.67532(16) 0.6252(2) 0.37911(16) 0.0518(8) Uani 1 1 d . . . . .
C72 C 0.66324(17) 0.6261(3) 0.43018(16) 0.0660(11) Uani 1 1 d . . . . .
H72 H 0.697246 0.630754 0.470419 0.079 Uiso 1 1 calc R U . . .
C73 C 0.60088(16) 0.6201(2) 0.42173(14) 0.0493(8) Uani 1 1 d . . . . .
C74 C 0.55131(15) 0.61269(19) 0.36401(14) 0.0422(6) Uani 1 1 d . . . . .
H74 H 0.508474 0.607958 0.358769 0.051 Uiso 1 1 calc R U . . .
C75 C 0.56484(16) 0.61225(19) 0.31393(14) 0.0442(7) Uani 1 1 d . . . . .
H75 H 0.530850 0.607628 0.273676 0.053 Uiso 1 1 calc R U . . .
C76 C 0.62686(16) 0.61840(19) 0.32095(14) 0.0432(7) Uani 1 1 d . . . . .
H76 H 0.635743 0.617927 0.286011 0.052 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
_geom_angle_publ_flag
C1 O1 H1A 109.5 . . ?
C4 O2 H2A 109.5 . . ?
O1 C1 C21 105.18(17) . . ?
O1 C1 C11 109.86(17) . . ?
C21 C1 C11 104.65(17) . . ?
O1 C1 C2 110.30(16) . . ?
C21 C1 C2 114.27(17) . . ?
C11 C1 C2 112.21(17) . . ?
C1 C2 C3 114.66(17) . . ?
C1 C2 C5 110.73(16) . . ?
C3 C2 C5 108.47(16) . . ?
C1 C2 H2 107.6 . . ?
C3 C2 H2 107.6 . . ?
C5 C2 H2 107.6 . . ?
C4 C3 C2 113.59(17) . . ?
C4 C3 C6 110.67(16) . . ?
C2 C3 C6 108.76(16) . . ?
C4 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
C6 C3 H3 107.9 . . ?
O2 C4 C31 105.85(17) . . ?
O2 C4 C41 109.52(17) . . ?
C31 C4 C41 103.39(16) . . ?
O2 C4 C3 110.24(16) . . ?
C31 C4 C3 114.33(17) . . ?
C41 C4 C3 113.06(17) . . ?
C61 C5 C51 106.63(18) . . ?
C61 C5 C2 107.33(17) . . ?
C51 C5 C2 107.67(18) . . ?
C61 C5 H5 111.6 . . ?
C51 C5 H5 111.6 . . ?
C2 C5 H5 111.6 . . ?
C62 C6 C52 106.78(18) . . ?
C62 C6 C3 107.68(18) . . ?
C52 C6 C3 107.29(17) . . ?
C62 C6 H6 111.6 . . ?
C52 C6 H6 111.6 . . ?
C3 C6 H6 111.6 . . ?
C12 C11 C16 118.2(2) . . ?
C12 C11 C1 120.1(2) . . ?
C16 C11 C1 121.5(2) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 Cl1 119.5(2) . . ?
C15 C14 Cl1 120.1(2) . . ?
C14 C15 C16 119.3(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C11 C16 C15 121.2(2) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C22 C21 C26 118.1(2) . . ?
C22 C21 C1 119.7(2) . . ?
C26 C21 C1 121.86(19) . . ?
C21 C22 C23 121.4(2) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 118.9(2) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C25 C24 C23 121.2(2) . . ?
C25 C24 Cl2 120.0(2) . . ?
C23 C24 Cl2 118.8(2) . . ?
C24 C25 C26 119.2(2) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C25 C26 C21 121.1(2) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
C32 C31 C36 118.0(2) . . ?
C32 C31 C4 122.60(19) . . ?
C36 C31 C4 118.9(2) . . ?
C33 C32 C31 121.2(2) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C34 C33 C32 119.4(2) . . ?
C34 C33 H33 120.3 . . ?
C32 C33 H33 120.3 . . ?
C35 C34 C33 120.6(2) . . ?
C35 C34 Cl3 119.60(19) . . ?
C33 C34 Cl3 119.8(2) . . ?
C34 C35 C36 119.4(2) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C35 C36 C31 121.4(2) . . ?
C35 C36 H36 119.3 . . ?
C31 C36 H36 119.3 . . ?
C46 C41 C42 117.8(2) . . ?
C46 C41 C4 121.8(2) . . ?
C42 C41 C4 120.2(2) . . ?
C43 C42 C41 121.4(3) . . ?
C43 C42 H42 119.3 . . ?
C41 C42 H42 119.3 . . ?
C44 C43 C42 119.5(3) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C43 C44 C45 120.6(2) . . ?
C43 C44 Cl4 119.7(2) . . ?
C45 C44 Cl4 119.7(2) . . ?
C44 C45 C46 119.2(2) . . ?
C44 C45 H45 120.4 . . ?
C46 C45 H45 120.4 . . ?
C45 C46 C41 121.5(2) . . ?
C45 C46 H46 119.2 . . ?
C41 C46 H46 119.2 . . ?
C56 C51 C52 120.6(2) . . ?
C56 C51 C5 126.5(2) . . ?
C52 C51 C5 112.9(2) . . ?
C53 C52 C51 120.0(2) . . ?
C53 C52 C6 126.7(2) . . ?
C51 C52 C6 113.3(2) . . ?
C52 C53 C54 119.3(3) . . ?
C52 C53 H53 120.4 . . ?
C54 C53 H53 120.4 . . ?
C55 C54 C53 120.5(3) . . ?
C55 C54 H54 119.7 . . ?
C53 C54 H54 119.7 . . ?
C54 C55 C56 120.5(2) . . ?
C54 C55 H55 119.8 . . ?
C56 C55 H55 119.8 . . ?
C51 C56 C55 119.1(3) . . ?
C51 C56 H56 120.5 . . ?
C55 C56 H56 120.5 . . ?
C66 C61 C62 120.6(2) . . ?
C66 C61 C5 125.9(2) . . ?
C62 C61 C5 113.5(2) . . ?
C63 C62 C61 120.0(2) . . ?
C63 C62 C6 127.2(2) . . ?
C61 C62 C6 112.76(19) . . ?
C62 C63 C64 119.6(2) . . ?
C62 C63 H63 120.2 . . ?
C64 C63 H63 120.2 . . ?
C65 C64 C63 120.2(2) . . ?
C65 C64 H64 119.9 . . ?
C63 C64 H64 119.9 . . ?
C64 C65 C66 120.6(3) . . ?
C64 C65 H65 119.7 . . ?
C66 C65 H65 119.7 . . ?
C61 C66 C65 119.0(2) . . ?
C61 C66 H66 120.5 . . ?
C65 C66 H66 120.5 . . ?
C76 C71 C72 121.3(3) . . ?
C76 C71 Cl71 119.5(3) . . ?
C72 C71 Cl71 119.2(3) . . ?
C71 C72 C73 118.6(3) . . ?
C71 C72 H72 120.7 . . ?
C73 C72 H72 120.7 . . ?
C74 C73 C72 121.4(3) . . ?
C74 C73 Cl72 119.0(3) . . ?
C72 C73 Cl72 119.5(3) . . ?
C73 C74 C75 118.6(3) . . ?
C73 C74 H74 120.7 . . ?
C75 C74 H74 120.7 . . ?
C74 C75 C76 121.2(3) . . ?
C74 C75 H75 119.4 . . ?
C76 C75 H75 119.4 . . ?
C71 C76 C75 118.8(3) . . ?
C71 C76 H76 120.6 . . ?
C75 C76 H76 120.6 . . ?
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
Cl1 C14 1.740(2) . ?
Cl2 C24 1.743(2) . ?
Cl3 C34 1.737(2) . ?
Cl4 C44 1.737(2) . ?
O1 C1 1.432(3) . ?
O1 H1A 0.8400 . ?
O2 C4 1.431(3) . ?
O2 H2A 0.8400 . ?
C1 C21 1.535(3) . ?
C1 C11 1.542(3) . ?
C1 C2 1.566(3) . ?
C2 C3 1.573(3) . ?
C2 C5 1.583(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.567(3) . ?
C3 C6 1.581(3) . ?
C3 H3 1.0000 . ?
C4 C31 1.535(3) . ?
C4 C41 1.540(3) . ?
C5 C61 1.511(3) . ?
C5 C51 1.515(3) . ?
C5 H5 1.0000 . ?
C6 C62 1.511(3) . ?
C6 C52 1.512(3) . ?
C6 H6 1.0000 . ?
C11 C12 1.384(3) . ?
C11 C16 1.388(3) . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.367(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(4) . ?
C15 C16 1.392(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.388(3) . ?
C21 C26 1.393(3) . ?
C22 C23 1.391(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(4) . ?
C25 C26 1.390(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.391(3) . ?
C31 C36 1.392(3) . ?
C32 C33 1.389(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.379(4) . ?
C35 C36 1.389(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.388(3) . ?
C41 C42 1.390(3) . ?
C42 C43 1.388(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.371(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.385(4) . ?
C45 C46 1.386(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C56 1.384(3) . ?
C51 C52 1.396(3) . ?
C52 C53 1.386(4) . ?
C53 C54 1.392(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.380(5) . ?
C54 H54 0.9500 . ?
C55 C56 1.392(4) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C61 C66 1.387(3) . ?
C61 C62 1.396(3) . ?
C62 C63 1.386(3) . ?
C63 C64 1.390(4) . ?
C63 H63 0.9500 . ?
C64 C65 1.386(4) . ?
C64 H64 0.9500 . ?
C65 C66 1.396(4) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
Cl71 C71 1.737(3) . ?
Cl72 C73 1.730(3) . ?
C71 C76 1.367(5) . ?
C71 C72 1.376(5) . ?
C72 C73 1.376(5) . ?
C72 H72 0.9500 . ?
C73 C74 1.371(4) . ?
C74 C75 1.373(4) . ?
C74 H74 0.9500 . ?
C75 C76 1.379(5) . ?
C75 H75 0.9500 . ?
C76 H76 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
C2 H2 O2 1.00 2.34 2.852(3) 111 . yes
C3 H3 O1 1.00 2.44 2.913(3) 108 . yes
C12 H12 O1 0.95 2.37 2.740(3) 103 . yes
C22 H22 O1 0.95 2.29 2.657(3) 102 . yes
C36 H36 O2 0.95 2.32 2.678(3) 102 . yes
C42 H42 O2 0.95 2.35 2.731(3) 104 . 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
O1 C1 C2 C3 -44.2(2) . . . . ?
C21 C1 C2 C3 74.0(2) . . . . ?
C11 C1 C2 C3 -167.02(17) . . . . ?
O1 C1 C2 C5 78.9(2) . . . . ?
C21 C1 C2 C5 -162.82(18) . . . . ?
C11 C1 C2 C5 -43.9(2) . . . . ?
C1 C2 C3 C4 -113.62(19) . . . . ?
C5 C2 C3 C4 122.04(19) . . . . ?
C1 C2 C3 C6 122.66(19) . . . . ?
C5 C2 C3 C6 -1.7(2) . . . . ?
C2 C3 C4 O2 -39.4(2) . . . . ?
C6 C3 C4 O2 83.3(2) . . . . ?
C2 C3 C4 C31 79.7(2) . . . . ?
C6 C3 C4 C31 -157.62(18) . . . . ?
C2 C3 C4 C41 -162.34(17) . . . . ?
C6 C3 C4 C41 -39.7(2) . . . . ?
C1 C2 C5 C61 177.22(18) . . . . ?
C3 C2 C5 C61 -56.1(2) . . . . ?
C1 C2 C5 C51 -68.3(2) . . . . ?
C3 C2 C5 C51 58.3(2) . . . . ?
C4 C3 C6 C62 -67.1(2) . . . . ?
C2 C3 C6 C62 58.4(2) . . . . ?
C4 C3 C6 C52 178.31(18) . . . . ?
C2 C3 C6 C52 -56.3(2) . . . . ?
O1 C1 C11 C12 12.9(3) . . . . ?
C21 C1 C11 C12 -99.5(2) . . . . ?
C2 C1 C11 C12 136.0(2) . . . . ?
O1 C1 C11 C16 -171.7(2) . . . . ?
C21 C1 C11 C16 75.9(2) . . . . ?
C2 C1 C11 C16 -48.6(3) . . . . ?
C16 C11 C12 C13 0.1(4) . . . . ?
C1 C11 C12 C13 175.7(2) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C12 C13 C14 C15 1.3(4) . . . . ?
C12 C13 C14 Cl1 -178.3(2) . . . . ?
C13 C14 C15 C16 -1.3(4) . . . . ?
Cl1 C14 C15 C16 178.3(2) . . . . ?
C12 C11 C16 C15 -0.2(4) . . . . ?
C1 C11 C16 C15 -175.6(2) . . . . ?
C14 C15 C16 C11 0.7(4) . . . . ?
O1 C1 C21 C22 -23.6(3) . . . . ?
C11 C1 C21 C22 92.2(2) . . . . ?
C2 C1 C21 C22 -144.7(2) . . . . ?
O1 C1 C21 C26 162.95(19) . . . . ?
C11 C1 C21 C26 -81.3(2) . . . . ?
C2 C1 C21 C26 41.8(3) . . . . ?
C26 C21 C22 C23 -1.2(4) . . . . ?
C1 C21 C22 C23 -174.9(2) . . . . ?
C21 C22 C23 C24 0.0(4) . . . . ?
C22 C23 C24 C25 1.2(4) . . . . ?
C22 C23 C24 Cl2 -178.1(2) . . . . ?
C23 C24 C25 C26 -1.2(4) . . . . ?
Cl2 C24 C25 C26 178.06(19) . . . . ?
C24 C25 C26 C21 0.0(4) . . . . ?
C22 C21 C26 C25 1.1(3) . . . . ?
C1 C21 C26 C25 174.7(2) . . . . ?
O2 C4 C31 C32 160.48(19) . . . . ?
C41 C4 C31 C32 -84.4(2) . . . . ?
C3 C4 C31 C32 38.9(3) . . . . ?
O2 C4 C31 C36 -28.0(3) . . . . ?
C41 C4 C31 C36 87.1(2) . . . . ?
C3 C4 C31 C36 -149.5(2) . . . . ?
C36 C31 C32 C33 1.0(3) . . . . ?
C4 C31 C32 C33 172.5(2) . . . . ?
C31 C32 C33 C34 -0.5(4) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
C32 C33 C34 Cl3 -179.53(19) . . . . ?
C33 C34 C35 C36 0.3(4) . . . . ?
Cl3 C34 C35 C36 179.67(19) . . . . ?
C34 C35 C36 C31 0.2(4) . . . . ?
C32 C31 C36 C35 -0.8(3) . . . . ?
C4 C31 C36 C35 -172.7(2) . . . . ?
O2 C4 C41 C46 -175.40(19) . . . . ?
C31 C4 C41 C46 72.1(2) . . . . ?
C3 C4 C41 C46 -52.0(3) . . . . ?
O2 C4 C41 C42 9.9(3) . . . . ?
C31 C4 C41 C42 -102.6(2) . . . . ?
C3 C4 C41 C42 133.2(2) . . . . ?
C46 C41 C42 C43 -1.1(4) . . . . ?
C4 C41 C42 C43 173.8(2) . . . . ?
C41 C42 C43 C44 -0.6(4) . . . . ?
C42 C43 C44 C45 2.3(4) . . . . ?
C42 C43 C44 Cl4 -177.2(2) . . . . ?
C43 C44 C45 C46 -2.1(4) . . . . ?
Cl4 C44 C45 C46 177.39(18) . . . . ?
C44 C45 C46 C41 0.3(4) . . . . ?
C42 C41 C46 C45 1.3(3) . . . . ?
C4 C41 C46 C45 -173.6(2) . . . . ?
C61 C5 C51 C56 -124.7(2) . . . . ?
C2 C5 C51 C56 120.4(2) . . . . ?
C61 C5 C51 C52 56.3(2) . . . . ?
C2 C5 C51 C52 -58.6(2) . . . . ?
C56 C51 C52 C53 -1.9(3) . . . . ?
C5 C51 C52 C53 177.2(2) . . . . ?
C56 C51 C52 C6 178.5(2) . . . . ?
C5 C51 C52 C6 -2.5(3) . . . . ?
C62 C6 C52 C53 126.7(2) . . . . ?
C3 C6 C52 C53 -118.1(2) . . . . ?
C62 C6 C52 C51 -53.6(2) . . . . ?
C3 C6 C52 C51 61.6(2) . . . . ?
C51 C52 C53 C54 1.6(3) . . . . ?
C6 C52 C53 C54 -178.7(2) . . . . ?
C52 C53 C54 C55 -0.2(4) . . . . ?
C53 C54 C55 C56 -1.0(4) . . . . ?
C52 C51 C56 C55 0.6(4) . . . . ?
C5 C51 C56 C55 -178.3(2) . . . . ?
C54 C55 C56 C51 0.8(4) . . . . ?
C51 C5 C61 C66 126.5(2) . . . . ?
C2 C5 C61 C66 -118.4(2) . . . . ?
C51 C5 C61 C62 -53.6(2) . . . . ?
C2 C5 C61 C62 61.6(2) . . . . ?
C66 C61 C62 C63 -1.1(3) . . . . ?
C5 C61 C62 C63 179.0(2) . . . . ?
C66 C61 C62 C6 177.5(2) . . . . ?
C5 C61 C62 C6 -2.4(3) . . . . ?
C52 C6 C62 C63 -125.2(2) . . . . ?
C3 C6 C62 C63 119.9(2) . . . . ?
C52 C6 C62 C61 56.4(2) . . . . ?
C3 C6 C62 C61 -58.6(2) . . . . ?
C61 C62 C63 C64 0.4(3) . . . . ?
C6 C62 C63 C64 -178.0(2) . . . . ?
C62 C63 C64 C65 0.6(4) . . . . ?
C63 C64 C65 C66 -0.8(4) . . . . ?
C62 C61 C66 C65 0.9(4) . . . . ?
C5 C61 C66 C65 -179.2(2) . . . . ?
C64 C65 C66 C61 0.1(4) . . . . ?
C76 C71 C72 C73 -0.1(6) . . . . ?
Cl71 C71 C72 C73 178.6(3) . . . . ?
C71 C72 C73 C74 0.5(6) . . . . ?
C71 C72 C73 Cl72 -179.6(3) . . . . ?
C72 C73 C74 C75 -0.7(6) . . . . ?
Cl72 C73 C74 C75 179.4(3) . . . . ?
C73 C74 C75 C76 0.5(5) . . . . ?
C72 C71 C76 C75 -0.1(5) . . . . ?
Cl71 C71 C76 C75 -178.8(3) . . . . ?
C74 C75 C76 C71 -0.1(5) . . . . ?
