#------------------------------------------------------------------------------
#$Date: 2021-11-06 21:48:05 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270414 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/35/7243566.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_7243566
loop_
_publ_author_name
'Barton, Benita'
'Barnardo, Brandon'
'Hosten, Eric C.'
_publ_section_title
;
 Selectivity behaviour of two roof-shaped host compounds in the presence
 of xylene and ethylbenzene guest mixtures
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              7278
_journal_page_last               7288
_journal_paper_doi               10.1039/D1CE01149A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C29 H22 Cl2 O, C8 H10'
_chemical_formula_sum            'C37 H32 Cl2 O'
_chemical_formula_weight         563.52
_chemical_melting_point          397.15
_chemical_name_systematic
;
α,α-Bis(p-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11-methanol
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-06-09 deposited with the CCDC.	2021-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                98.370(17)
_cell_angle_beta                 96.251(17)
_cell_angle_gamma                103.375(17)
_cell_formula_units_Z            2
_cell_length_a                   9.760(4)
_cell_length_b                   10.850(4)
_cell_length_c                   15.146(5)
_cell_measurement_reflns_used    6952
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.39
_cell_volume                     1526.8(10)
_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      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.974
_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  0.0269
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21529
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.467
_diffrn_reflns_theta_min         1.960
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9521
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.330
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         7515
_refine_ls_number_restraints     124
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0527
_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)+(0.0727P)²+0.3633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4946
_reflns_number_total             7515
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01149a2.cif
_cod_data_source_block           ja169
_cod_depositor_comments
'Adding full bibliography for 7243566--7243569.cif.'
_cod_original_cell_volume        1526.7(10)
_cod_database_code               7243566
_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   0.896
_shelx_estimated_absorpt_t_max   0.925
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.78226(9) 1.07369(7) 0.58053(5) 0.0963(3) Uani 1 1 d . . . . .
Cl2 Cl 0.63633(9) 0.16660(7) 0.34268(5) 0.0975(3) Uani 1 1 d . . . . .
O1 O 0.71491(13) 0.70354(13) 0.17842(9) 0.0501(3) Uani 1 1 d . . . . .
H1 H 0.701903 0.760353 0.150700 0.075 Uiso 1 1 calc R U . . .
C1 C 0.60882(17) 0.67872(16) 0.23588(11) 0.0388(4) Uani 1 1 d . . . . .
C2 C 0.46008(17) 0.67758(15) 0.18660(11) 0.0364(3) Uani 1 1 d . . . . .
H2 H 0.390686 0.651212 0.226717 0.044 Uiso 1 1 calc R U . . .
C3 C 0.44654(18) 0.81271(15) 0.16639(11) 0.0381(4) Uani 1 1 d . . . . .
H3 H 0.477369 0.879725 0.220396 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4147(2) 0.57884(16) 0.09729(11) 0.0432(4) Uani 1 1 d . . . . .
H4A H 0.340307 0.506382 0.105096 0.052 Uiso 1 1 calc R U . . .
H4B H 0.495380 0.546898 0.081431 0.052 Uiso 1 1 calc R U . . .
C5 C 0.3593(2) 0.64338(17) 0.02029(11) 0.0447(4) Uani 1 1 d . . . . .
H5 H 0.326137 0.582052 -0.036491 0.054 Uiso 1 1 calc R U . . .
C11 C 0.65182(18) 0.77942(16) 0.32315(11) 0.0399(4) Uani 1 1 d . . . . .
C12 C 0.5598(2) 0.7859(2) 0.38599(13) 0.0534(5) Uani 1 1 d . . . . .
H12 H 0.470119 0.728811 0.375022 0.064 Uiso 1 1 calc R U . . .
C13 C 0.5990(2) 0.8759(2) 0.46500(14) 0.0615(5) Uani 1 1 d . . . . .
H13 H 0.535932 0.879523 0.506544 0.074 Uiso 1 1 calc R U . . .
C14 C 0.7320(2) 0.95999(19) 0.48156(14) 0.0572(5) Uani 1 1 d . . . . .
C15 C 0.8248(2) 0.9557(2) 0.42132(15) 0.0631(6) Uani 1 1 d . . . . .
H15 H 0.914355 1.013121 0.432708 0.076 Uiso 1 1 calc R U . . .
C16 C 0.7848(2) 0.8652(2) 0.34280(14) 0.0533(5) Uani 1 1 d . . . . .
H16 H 0.849168 0.861775 0.302052 0.064 Uiso 1 1 calc R U . . .
C21 C 0.61112(18) 0.54671(17) 0.26118(11) 0.0402(4) Uani 1 1 d . . . . .
C22 C 0.7299(2) 0.5001(2) 0.25358(14) 0.0562(5) Uani 1 1 d . . . . .
H22 H 0.806095 0.547549 0.230972 0.067 Uiso 1 1 calc R U . . .
C23 C 0.7383(2) 0.3842(2) 0.27888(16) 0.0665(6) Uani 1 1 d . . . . .
H23 H 0.819500 0.354334 0.273426 0.080 Uiso 1 1 calc R U . . .
C24 C 0.6265(2) 0.3138(2) 0.31190(14) 0.0588(5) Uani 1 1 d . . . . .
C25 C 0.5070(2) 0.3568(2) 0.32087(16) 0.0627(6) Uani 1 1 d . . . . .
H25 H 0.431672 0.308977 0.344035 0.075 Uiso 1 1 calc R U . . .
C26 C 0.4994(2) 0.4731(2) 0.29489(14) 0.0550(5) Uani 1 1 d . . . . .
H26 H 0.417639 0.502157 0.300225 0.066 Uiso 1 1 calc R U . . .
C31 C 0.52933(19) 0.84558(16) 0.09043(12) 0.0421(4) Uani 1 1 d . . . . .
C32 C 0.4821(2) 0.75337(17) 0.01152(12) 0.0454(4) Uani 1 1 d . . . . .
C33 C 0.5492(3) 0.7680(2) -0.06358(14) 0.0606(6) Uani 1 1 d . . . . .
H33 H 0.519233 0.707202 -0.116286 0.073 Uiso 1 1 calc R U . . .
C34 C 0.6614(3) 0.8741(2) -0.05922(18) 0.0753(7) Uani 1 1 d . . . . .
H34 H 0.706963 0.883641 -0.109547 0.090 Uiso 1 1 calc R U . . .
C35 C 0.7074(3) 0.9659(2) 0.01734(19) 0.0714(7) Uani 1 1 d . . . . .
H35 H 0.782457 1.036934 0.018285 0.086 Uiso 1 1 calc R U . . .
C36 C 0.6414(2) 0.95242(19) 0.09375(15) 0.0550(5) Uani 1 1 d . . . . .
H36 H 0.671862 1.013987 0.146049 0.066 Uiso 1 1 calc R U . . .
C41 C 0.29007(19) 0.79205(16) 0.13060(11) 0.0415(4) Uani 1 1 d . . . . .
C42 C 0.2425(2) 0.70027(17) 0.05171(12) 0.0446(4) Uani 1 1 d . . . . .
C43 C 0.1014(2) 0.6691(2) 0.01280(15) 0.0608(5) Uani 1 1 d . . . . .
H43 H 0.070039 0.607269 -0.039303 0.073 Uiso 1 1 calc R U . . .
C44 C 0.0069(2) 0.7294(3) 0.05098(19) 0.0746(7) Uani 1 1 d . . . . .
H44 H -0.088009 0.708658 0.024698 0.089 Uiso 1 1 calc R U . . .
C45 C 0.0536(2) 0.8202(3) 0.12787(18) 0.0711(7) Uani 1 1 d . . . . .
H45 H -0.010374 0.861119 0.153160 0.085 Uiso 1 1 calc R U . . .
C46 C 0.1954(2) 0.85241(19) 0.16904(14) 0.0523(5) Uani 1 1 d . . . . .
H46 H 0.225621 0.913604 0.221550 0.063 Uiso 1 1 calc R U . . .
C51 C 0.1364(2) 0.3964(2) 0.38794(11) 0.0693(8) Uani 0.845(4) 1 d DG . P A 1
C52 C 0.1112(2) 0.31834(14) 0.30355(13) 0.0733(9) Uani 0.845(4) 1 d DG . P A 1
C53 C 0.0974(2) 0.37147(18) 0.22591(10) 0.0692(8) Uani 0.845(4) 1 d DG . P A 1
H53 H 0.080586 0.319223 0.169447 0.083 Uiso 0.845(4) 1 calc R U P A 1
C54 C 0.1087(2) 0.50269(19) 0.23266(13) 0.0752(9) Uani 0.845(4) 1 d DG . P A 1
H54 H 0.099500 0.538237 0.180719 0.090 Uiso 0.845(4) 1 calc R U P A 1
C55 C 0.1339(2) 0.58078(14) 0.31706(16) 0.0754(8) Uani 0.845(4) 1 d DG . P A 1
H55 H 0.141473 0.668572 0.321573 0.091 Uiso 0.845(4) 1 calc R U P A 1
C56 C 0.1477(3) 0.52765(19) 0.39469(12) 0.0873(10) Uani 0.845(4) 1 d DG . P A 1
H56 H 0.164531 0.579893 0.451157 0.105 Uiso 0.845(4) 1 calc R U P A 1
C57 C 0.1476(6) 0.3401(6) 0.4748(3) 0.139(2) Uani 0.845(4) 1 d D . P A 1
H57A H 0.165052 0.407968 0.526111 0.209 Uiso 0.845(4) 1 calc R U P A 1
H57B H 0.060101 0.278256 0.476085 0.209 Uiso 0.845(4) 1 calc R U P A 1
H57C H 0.224579 0.298764 0.476645 0.209 Uiso 0.845(4) 1 calc R U P A 1
C58 C 0.0930(5) 0.1790(3) 0.2927(4) 0.1182(16) Uani 0.845(4) 1 d D . P A 1
H58A H 0.076743 0.142688 0.229599 0.177 Uiso 0.845(4) 1 calc R U P A 1
H58B H 0.177328 0.161152 0.321132 0.177 Uiso 0.845(4) 1 calc R U P A 1
H58C H 0.012890 0.141700 0.320169 0.177 Uiso 0.845(4) 1 calc R U P A 1
C61 C 0.141(2) 0.332(2) 0.4058(16) 0.171(7) Uani 0.155(4) 1 d DG U P A 2
C62 C 0.105(2) 0.352(2) 0.3184(14) 0.171(7) Uani 0.155(4) 1 d DG U P A 2
C63 C 0.114(2) 0.476(3) 0.3016(15) 0.171(7) Uani 0.155(4) 1 d DG U P A 2
H63 H 0.090549 0.488724 0.243183 0.206 Uiso 0.155(4) 1 calc R U P A 2
C64 C 0.159(2) 0.580(2) 0.372(2) 0.171(7) Uani 0.155(4) 1 d DG U P A 2
H64 H 0.164847 0.662933 0.360937 0.206 Uiso 0.155(4) 1 calc R U P A 2
C65 C 0.195(2) 0.560(2) 0.4595(17) 0.171(7) Uani 0.155(4) 1 d DG U P A 2
H65 H 0.224297 0.630216 0.506717 0.206 Uiso 0.155(4) 1 calc R U P A 2
C66 C 0.186(2) 0.436(3) 0.4763(13) 0.171(7) Uani 0.155(4) 1 d DG U P A 2
H66 H 0.209450 0.423292 0.534743 0.206 Uiso 0.155(4) 1 calc R U P A 2
C67 C 0.134(3) 0.193(2) 0.404(2) 0.171(7) Uani 0.155(4) 1 d D U P A 2
H67A H 0.158330 0.178810 0.464446 0.257 Uiso 0.155(4) 1 calc R U P A 2
H67B H 0.038888 0.142492 0.380257 0.257 Uiso 0.155(4) 1 calc R U P A 2
H67C H 0.199404 0.167113 0.366899 0.257 Uiso 0.155(4) 1 calc R U P A 2
C68 C 0.076(3) 0.248(3) 0.2326(18) 0.171(7) Uani 0.155(4) 1 d D U P A 2
H68A H 0.071370 0.165290 0.249374 0.257 Uiso 0.155(4) 1 calc R U P A 2
H68B H -0.012837 0.246614 0.197919 0.257 Uiso 0.155(4) 1 calc R U P A 2
H68C H 0.151397 0.267558 0.197101 0.257 Uiso 0.155(4) 1 calc R U P A 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'
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
C1 O1 H1 109.5 . . ?
O1 C1 C11 109.48(14) . . ?
O1 C1 C21 105.62(13) . . ?
C11 C1 C21 107.75(13) . . ?
O1 C1 C2 110.83(13) . . ?
C11 C1 C2 111.53(13) . . ?
C21 C1 C2 111.42(14) . . ?
C4 C2 C1 112.86(13) . . ?
C4 C2 C3 108.52(13) . . ?
C1 C2 C3 113.98(13) . . ?
C4 C2 H2 107.0 . . ?
C1 C2 H2 107.0 . . ?
C3 C2 H2 107.0 . . ?
C31 C3 C41 107.10(14) . . ?
C31 C3 C2 109.05(13) . . ?
C41 C3 C2 104.49(13) . . ?
C31 C3 H3 111.9 . . ?
C41 C3 H3 111.9 . . ?
C2 C3 H3 111.9 . . ?
C2 C4 C5 110.01(13) . . ?
C2 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C2 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C42 C5 C32 107.83(14) . . ?
C42 C5 C4 107.27(14) . . ?
C32 C5 C4 106.23(15) . . ?
C42 C5 H5 111.7 . . ?
C32 C5 H5 111.7 . . ?
C4 C5 H5 111.7 . . ?
C12 C11 C16 117.45(17) . . ?
C12 C11 C1 121.11(16) . . ?
C16 C11 C1 121.42(15) . . ?
C11 C12 C13 121.11(19) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 119.52(19) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.73(19) . . ?
C15 C14 Cl1 119.38(18) . . ?
C13 C14 Cl1 119.89(18) . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 121.89(19) . . ?
C11 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C22 C21 C26 117.66(17) . . ?
C22 C21 C1 119.64(16) . . ?
C26 C21 C1 122.65(15) . . ?
C21 C22 C23 121.41(19) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 119.59(18) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 120.86(18) . . ?
C23 C24 Cl2 119.59(16) . . ?
C25 C24 Cl2 119.54(17) . . ?
C24 C25 C26 119.07(19) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C21 C26 C25 121.40(17) . . ?
C21 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C36 C31 C32 120.74(17) . . ?
C36 C31 C3 126.72(17) . . ?
C32 C31 C3 112.55(15) . . ?
C33 C32 C31 119.61(19) . . ?
C33 C32 C5 126.91(18) . . ?
C31 C32 C5 113.47(15) . . ?
C34 C33 C32 119.1(2) . . ?
C34 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
C35 C34 C33 121.8(2) . . ?
C35 C34 H34 119.1 . . ?
C33 C34 H34 119.1 . . ?
C34 C35 C36 119.9(2) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C31 C36 C35 118.9(2) . . ?
C31 C36 H36 120.6 . . ?
C35 C36 H36 120.6 . . ?
C46 C41 C42 119.60(18) . . ?
C46 C41 C3 126.44(17) . . ?
C42 C41 C3 113.95(14) . . ?
C43 C42 C41 120.29(18) . . ?
C43 C42 C5 127.42(18) . . ?
C41 C42 C5 112.28(16) . . ?
C44 C43 C42 120.2(2) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C45 C44 C43 119.7(2) . . ?
C45 C44 H44 120.2 . . ?
C43 C44 H44 120.2 . . ?
C44 C45 C46 121.3(2) . . ?
C44 C45 H45 119.4 . . ?
C46 C45 H45 119.4 . . ?
C41 C46 C45 119.0(2) . . ?
C41 C46 H46 120.5 . . ?
C45 C46 H46 120.5 . . ?
C52 C51 C56 120.0 . . ?
C52 C51 C57 121.2(3) . . ?
C56 C51 C57 118.7(3) . . ?
C51 C52 C53 120.0 . . ?
C51 C52 C58 122.2(3) . . ?
C53 C52 C58 117.8(3) . . ?
C54 C53 C52 120.0 . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C55 C54 C53 120.0 . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C54 C55 C56 120.0 . . ?
C54 C55 H55 120.0 . . ?
C56 C55 H55 120.0 . . ?
C55 C56 C51 120.0 . . ?
C55 C56 H56 120.0 . . ?
C51 C56 H56 120.0 . . ?
C51 C57 H57A 109.5 . . ?
C51 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C51 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C52 C58 H58A 109.5 . . ?
C52 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C52 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C62 C61 C66 120.0 . . ?
C62 C61 C67 109.3(16) . . ?
C66 C61 C67 130.5(16) . . ?
C63 C62 C61 120.0 . . ?
C63 C62 C68 114.2(17) . . ?
C61 C62 C68 125.2(17) . . ?
C62 C63 C64 120.0 . . ?
C62 C63 H63 120.0 . . ?
C64 C63 H63 120.0 . . ?
C65 C64 C63 120.0 . . ?
C65 C64 H64 120.0 . . ?
C63 C64 H64 120.0 . . ?
C64 C65 C66 120.0 . . ?
C64 C65 H65 120.0 . . ?
C66 C65 H65 120.0 . . ?
C65 C66 C61 120.0 . . ?
C65 C66 H66 120.0 . . ?
C61 C66 H66 120.0 . . ?
C61 C67 H67A 109.5 . . ?
C61 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
C61 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C62 C68 H68A 109.5 . . ?
C62 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
C62 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
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 1.741(2) . ?
Cl2 C24 1.748(2) . ?
O1 C1 1.4273(19) . ?
O1 H1 0.8200 . ?
C1 C11 1.538(2) . ?
C1 C21 1.540(2) . ?
C1 C2 1.555(2) . ?
C2 C4 1.550(2) . ?
C2 C3 1.572(2) . ?
C2 H2 0.9800 . ?
C3 C31 1.514(2) . ?
C3 C41 1.517(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.555(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C42 1.506(3) . ?
C5 C32 1.516(3) . ?
C5 H5 0.9800 . ?
C11 C12 1.383(2) . ?
C11 C16 1.384(3) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.357(3) . ?
C15 C16 1.383(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C22 1.377(2) . ?
C21 C26 1.388(3) . ?
C22 C23 1.385(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.367(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.366(3) . ?
C25 C26 1.391(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C31 C36 1.388(3) . ?
C31 C32 1.400(3) . ?
C32 C33 1.384(3) . ?
C33 C34 1.381(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.371(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.394(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C41 C46 1.381(3) . ?
C41 C42 1.398(3) . ?
C42 C43 1.381(3) . ?
C43 C44 1.377(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.370(4) . ?
C44 H44 0.9300 . ?
C45 C46 1.397(3) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C51 C52 1.3900 . ?
C51 C56 1.3900 . ?
C51 C57 1.533(4) . ?
C52 C53 1.3900 . ?
C52 C58 1.463(4) . ?
C53 C54 1.3900 . ?
C53 H53 0.9300 . ?
C54 C55 1.3900 . ?
C54 H54 0.9300 . ?
C55 C56 1.3900 . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C61 C62 1.3900 . ?
C61 C66 1.3900 . ?
C61 C67 1.494(15) . ?
C62 C63 1.3900 . ?
C62 C68 1.543(14) . ?
C63 C64 1.3900 . ?
C63 H63 0.9300 . ?
C64 C65 1.3900 . ?
C64 H64 0.9300 . ?
C65 C66 1.3900 . ?
C65 H65 0.9300 . ?
C66 H66 0.9300 . ?
C67 H67A 0.9600 . ?
C67 H67B 0.9600 . ?
C67 H67C 0.9600 . ?
C68 H68A 0.9600 . ?
C68 H68B 0.9600 . ?
C68 H68C 0.9600 . ?
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
C4 H4B O1 0.97 2.56 2.970(3) 106 . yes
C16 H16 O1 0.93 2.38 2.747(3) 103 . yes
C22 H22 O1 0.93 2.29 2.652(3) 103 . 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 C4 56.64(18) . . . . ?
C11 C1 C2 C4 178.89(13) . . . . ?
C21 C1 C2 C4 -60.66(17) . . . . ?
O1 C1 C2 C3 -67.76(17) . . . . ?
C11 C1 C2 C3 54.50(17) . . . . ?
C21 C1 C2 C3 174.95(12) . . . . ?
C4 C2 C3 C31 -53.51(18) . . . . ?
C1 C2 C3 C31 73.18(17) . . . . ?
C4 C2 C3 C41 60.73(16) . . . . ?
C1 C2 C3 C41 -172.58(13) . . . . ?
C1 C2 C4 C5 -132.13(15) . . . . ?
C3 C2 C4 C5 -4.79(19) . . . . ?
C2 C4 C5 C42 -54.84(19) . . . . ?
C2 C4 C5 C32 60.28(17) . . . . ?
O1 C1 C11 C12 172.73(16) . . . . ?
C21 C1 C11 C12 -72.9(2) . . . . ?
C2 C1 C11 C12 49.7(2) . . . . ?
O1 C1 C11 C16 -8.7(2) . . . . ?
C21 C1 C11 C16 105.74(18) . . . . ?
C2 C1 C11 C16 -131.69(17) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
C1 C11 C12 C13 179.44(17) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C12 C13 C14 Cl1 179.89(16) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
Cl1 C14 C15 C16 179.87(16) . . . . ?
C12 C11 C16 C15 -1.0(3) . . . . ?
C1 C11 C16 C15 -179.70(18) . . . . ?
C14 C15 C16 C11 0.9(3) . . . . ?
O1 C1 C21 C22 20.8(2) . . . . ?
C11 C1 C21 C22 -96.18(19) . . . . ?
C2 C1 C21 C22 141.17(17) . . . . ?
O1 C1 C21 C26 -161.62(17) . . . . ?
C11 C1 C21 C26 81.4(2) . . . . ?
C2 C1 C21 C26 -41.2(2) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?
C1 C21 C22 C23 177.52(19) . . . . ?
C21 C22 C23 C24 0.2(4) . . . . ?
C22 C23 C24 C25 -0.5(4) . . . . ?
C22 C23 C24 Cl2 179.31(18) . . . . ?
C23 C24 C25 C26 0.7(4) . . . . ?
Cl2 C24 C25 C26 -179.02(18) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
C1 C21 C26 C25 -177.15(19) . . . . ?
C24 C25 C26 C21 -0.8(4) . . . . ?
C41 C3 C31 C36 126.27(18) . . . . ?
C2 C3 C31 C36 -121.20(19) . . . . ?
C41 C3 C31 C32 -54.31(18) . . . . ?
C2 C3 C31 C32 58.23(18) . . . . ?
C36 C31 C32 C33 0.9(3) . . . . ?
C3 C31 C32 C33 -178.53(16) . . . . ?
C36 C31 C32 C5 179.85(16) . . . . ?
C3 C31 C32 C5 0.4(2) . . . . ?
C42 C5 C32 C33 -126.48(19) . . . . ?
C4 C5 C32 C33 118.78(19) . . . . ?
C42 C5 C32 C31 54.69(19) . . . . ?
C4 C5 C32 C31 -60.05(18) . . . . ?
C31 C32 C33 C34 -0.4(3) . . . . ?
C5 C32 C33 C34 -179.12(19) . . . . ?
C32 C33 C34 C35 -0.5(3) . . . . ?
C33 C34 C35 C36 0.7(4) . . . . ?
C32 C31 C36 C35 -0.7(3) . . . . ?
C3 C31 C36 C35 178.71(18) . . . . ?
C34 C35 C36 C31 -0.1(3) . . . . ?
C31 C3 C41 C46 -126.27(18) . . . . ?
C2 C3 C41 C46 118.12(18) . . . . ?
C31 C3 C41 C42 54.89(18) . . . . ?
C2 C3 C41 C42 -60.72(17) . . . . ?
C46 C41 C42 C43 -0.6(3) . . . . ?
C3 C41 C42 C43 178.32(16) . . . . ?
C46 C41 C42 C5 -179.19(15) . . . . ?
C3 C41 C42 C5 -0.3(2) . . . . ?
C32 C5 C42 C43 127.3(2) . . . . ?
C4 C5 C42 C43 -118.7(2) . . . . ?
C32 C5 C42 C41 -54.24(18) . . . . ?
C4 C5 C42 C41 59.80(19) . . . . ?
C41 C42 C43 C44 0.7(3) . . . . ?
C5 C42 C43 C44 179.09(19) . . . . ?
C42 C43 C44 C45 -0.2(3) . . . . ?
C43 C44 C45 C46 -0.5(4) . . . . ?
C42 C41 C46 C45 -0.1(3) . . . . ?
C3 C41 C46 C45 -178.83(18) . . . . ?
C44 C45 C46 C41 0.6(3) . . . . ?
C56 C51 C52 C53 0.0 . . . . ?
C57 C51 C52 C53 178.1(3) . . . . ?
C56 C51 C52 C58 -177.6(3) . . . . ?
C57 C51 C52 C58 0.5(4) . . . . ?
C51 C52 C53 C54 0.0 . . . . ?
C58 C52 C53 C54 177.7(3) . . . . ?
C52 C53 C54 C55 0.0 . . . . ?
C53 C54 C55 C56 0.0 . . . . ?
C54 C55 C56 C51 0.0 . . . . ?
C52 C51 C56 C55 0.0 . . . . ?
C57 C51 C56 C55 -178.2(3) . . . . ?
C66 C61 C62 C63 0.0 . . . . ?
C67 C61 C62 C63 -175(2) . . . . ?
C66 C61 C62 C68 171(2) . . . . ?
C67 C61 C62 C68 -5(2) . . . . ?
C61 C62 C63 C64 0.0 . . . . ?
C68 C62 C63 C64 -172(2) . . . . ?
C62 C63 C64 C65 0.0 . . . . ?
C63 C64 C65 C66 0.0 . . . . ?
C64 C65 C66 C61 0.0 . . . . ?
C62 C61 C66 C65 0.0 . . . . ?
C67 C61 C66 C65 174(3) . . . . ?
