# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3ODICL
_database_code_depnum_ccdc_archive 'CCDC 2329242'
loop_
_audit_author_name
_audit_author_address
'Mino Caira'
;University of Cape Town
South Africa
;
_audit_update_record             
;
2024-01-29 deposited with the CCDC.	2024-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"trans-alpha, alpha, alpha',alpha'-tetraphenyl-9,10-dihydro-9,10-ethano-anthracene-11,12-dimethanol 1,2-dichlorobenzene clathrate"
_chemical_melting_point          'decomp. (guest loss) onset 333 K'
_chemical_formula_moiety         'C42 H34 O2, C6 H4 Cl2'
_chemical_formula_sum            'C48 H38 Cl2 O2'
_chemical_formula_weight         717.68

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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'

_cell_length_a                   12.4249(18)
_cell_length_b                   11.7971(18)
_cell_length_c                   24.951(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.752(3)
_cell_angle_gamma                90
_cell_volume                     3638.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.23

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.219
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2851
_exptl_absorpt_correction_T_max  0.3600
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   'appended - end of file'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE SCXRD diffractometer'
_diffrn_measurement_method       'omega-and phi-scans, width 0.5 deg.'
_diffrn_detector_area_resol_mean n/a
_diffrn_reflns_number            77693
_diffrn_reflns_av_unetI/netI     0.1076
_diffrn_reflns_av_R_equivalents  0.1398
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.641
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9059
_reflns_number_gt                6691
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Apex3 v2019.1-0, Bruker (2019).'
_computing_cell_refinement       
'SAINT V8.40A, Bruker AXS Inc.: Madison (WI), USA.'
_computing_data_reduction        
'SAINT V8.40A, Bruker AXS Inc.: Madison (WI), USA.'
_computing_structure_solution    'SHELXS-Version 2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'POV-Ray in interface X-Seed (LJ Barbour, 1999)'
_computing_publication_material  'PLATON (Spek, 1990)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²+1.4386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9059
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1722
_refine_ls_wR_factor_gt          0.1510
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.670
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.068


_chemical_name_common            none
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,2-dichlorobenzene'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ma036_tw
_database_code_depnum_ccdc_archive 'CCDC 2330021'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2024-01-31 deposited with the CCDC.	2024-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            
"trans- α,α,α',α'-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol"
_chemical_melting_point          331.05
_chemical_formula_moiety         'C42 H30 Cl4 O2, C6 H4 Cl2'
_chemical_formula_sum            'C48 H34 Cl6 O2'
_chemical_formula_weight         855.45

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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.
;

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'

_cell_length_a                   23.2360(10)
_cell_length_b                   15.6145(8)
_cell_length_c                   24.0913(10)
_cell_angle_alpha                90
_cell_angle_beta                 115.807(3)
_cell_angle_gamma                90
_cell_volume                     7869.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9750
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.30

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             3520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.665
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.478
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.656407
_exptl_absorpt_correction_T_max  0.745686
_exptl_absorpt_process_details   'TWINABS 2012/1 (Bruker AXS)'
_exptl_absorpt_special_details   
;  
Additional spherical absorption correction applied with mu*r =  0.2000
Details of twinning from .abs file
;
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            9829
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.607
_diffrn_reflns_theta_max         28.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9829
_reflns_number_gt                8170
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;All non-hydrogen atoms were refined anisotropically. Carbon-bound H atoms were
placed in calculated positions and were included in the refinement in the riding
model approximation, with Uiso(H) set to 1.2 Ueq(C).

The H atoms of the hydroxyl groups were allowed to rotate with a fixed angle
around the C---O bonds to best fit the experimental electron density (HFIX 147
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(O).

Refined as a 2-component twin.

A reflection with large difference between its observed and calculated
intensities was omitted. This is due to obstruction by the beam stop.,Twin
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+12.9357P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9829
_refine_ls_number_parameters     508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: m-dichlorobenzene'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ma166
_database_code_depnum_ccdc_archive 'CCDC 2330022'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2024-01-31 deposited with the CCDC.	2024-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            
trans-α,α,α',α'-tetra(p-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol
_chemical_melting_point          432.05
_chemical_formula_moiety         'C42 H34 O2, 0.333(C6 H4 Cl2)'
_chemical_formula_sum            'C44 H35.33 Cl0.67 O2'
_chemical_formula_weight         619.69

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   23.2834(9)
_cell_length_b                   23.2834(9)
_cell_length_c                   12.4263(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6736.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.17

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             2613
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.731
_exptl_crystal_size_mid          0.674
_exptl_crystal_size_min          0.440
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8772
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            44314
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.749
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8217
_reflns_number_gt                6147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_max     0.960
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;All non-hydrogen atoms were refined anisotropically. Carbon-bound H atoms were
placed in calculated positions and were included in the refinement in the riding
model approximation, with Uiso(H) set to 1.2 Ueq(C).

The H atoms of the hydroxyl groups were allowed to rotate with a fixed angle
around the C---O bonds to best fit the experimental electron density (HFIX 147
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(O).

The solvent m-dichlorobenzene is disordered around a 4-fold rotoinversion axis
in a channel void. A number of restraints and constraints had to be used. The
occupancy of the solvent was set as a free variable which refined to 0.37. The
occupancy was then fixed at one third.

A reflection with large difference between its observed and calculated
intensities was omitted. This is due to obstruction by the beam stop.,disorder
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1150P)²+1.2252P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2390 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8217
_refine_ls_number_parameters     460
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1771
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.48430(10) 0.70388(10) 0.8445(2) 0.0557(6) Uani 1 1 d . . . . .
H1A H 0.514402 0.720783 0.831499 0.084 Uiso 1 1 calc R U . . .
O2 O 0.35597(9) 0.79164(9) 0.5603(2) 0.0496(5) Uani 1 1 d . . . . .
H2A H 0.379192 0.816533 0.543354 0.074 Uiso 1 1 calc R U . . .
C1 C 0.43812(12) 0.74411(13) 0.8469(2) 0.0417(6) Uani 1 1 d . . . . .
C2 C 0.43458(12) 0.77814(11) 0.7382(2) 0.0362(5) Uani 1 1 d . . . . .
H2 H 0.396948 0.796941 0.735726 0.043 Uiso 1 1 calc R U . . .
C3 C 0.44051(12) 0.74098(11) 0.6332(2) 0.0378(6) Uani 1 1 d . . . . .
H3 H 0.450574 0.701866 0.655429 0.045 Uiso 1 1 calc R U . . .
C4 C 0.38417(13) 0.73702(12) 0.5638(3) 0.0418(6) Uani 1 1 d . . . . .
C5 C 0.48175(12) 0.82696(12) 0.7349(2) 0.0392(6) Uani 1 1 d . . . . .
H5 H 0.479460 0.851853 0.798294 0.047 Uiso 1 1 calc R U . . .
C6 C 0.49205(12) 0.76493(12) 0.5647(2) 0.0401(6) Uani 1 1 d . . . . .
H6 H 0.497723 0.742547 0.498786 0.048 Uiso 1 1 calc R U . . .
C11 C 0.44470(14) 0.78593(14) 0.9424(3) 0.0473(7) Uani 1 1 d . . . . .
C12 C 0.40753(16) 0.83285(16) 0.9549(3) 0.0574(8) Uani 1 1 d . . . . .
H12 H 0.378313 0.838938 0.905186 0.069 Uiso 1 1 calc R U . . .
C13 C 0.4140(2) 0.87005(19) 1.0405(4) 0.0759(13) Uani 1 1 d . . . . .
H13 H 0.389162 0.901091 1.047605 0.091 Uiso 1 1 calc R U . . .
C14 C 0.4562(3) 0.8619(3) 1.1143(4) 0.0902(17) Uani 1 1 d . . . . .
H14 H 0.460011 0.887191 1.171872 0.108 Uiso 1 1 calc R U . . .
C15 C 0.4928(3) 0.8166(3) 1.1039(4) 0.0892(16) Uani 1 1 d . . . . .
H15 H 0.521866 0.811286 1.154290 0.107 Uiso 1 1 calc R U . . .
C16 C 0.48716(18) 0.7786(2) 1.0194(3) 0.0661(10) Uani 1 1 d . . . . .
H16 H 0.512225 0.747673 1.013941 0.079 Uiso 1 1 calc R U . . .
C21 C 0.38413(14) 0.70887(14) 0.8747(3) 0.0481(7) Uani 1 1 d . . . . .
C22 C 0.3898(2) 0.65755(18) 0.9309(3) 0.0679(10) Uani 1 1 d . . . . .
H22 H 0.426245 0.643241 0.945646 0.081 Uiso 1 1 calc R U . . .
C23 C 0.3420(3) 0.6275(2) 0.9653(4) 0.0891(16) Uani 1 1 d . . . . .
H23 H 0.346470 0.593173 1.002764 0.107 Uiso 1 1 calc R U . . .
C24 C 0.2873(2) 0.6482(2) 0.9441(4) 0.0790(13) Uani 1 1 d . . . . .
H24 H 0.255107 0.627918 0.966677 0.095 Uiso 1 1 calc R U . . .
C25 C 0.28157(17) 0.6981(2) 0.8904(3) 0.0683(11) Uani 1 1 d . . . . .
H25 H 0.245010 0.712473 0.876699 0.082 Uiso 1 1 calc R U . . .
C26 C 0.32936(14) 0.72863(15) 0.8552(3) 0.0525(8) Uani 1 1 d . . . . .
H26 H 0.324265 0.762874 0.817870 0.063 Uiso 1 1 calc R U . . .
C31 C 0.39732(14) 0.71697(15) 0.4473(3) 0.0515(8) Uani 1 1 d . . . . .
C32 C 0.4253(2) 0.6662(2) 0.4283(4) 0.0756(12) Uani 1 1 d . . . . .
H32 H 0.435977 0.643057 0.485857 0.091 Uiso 1 1 calc R U . . .
C33 C 0.4378(3) 0.6489(3) 0.3236(5) 0.1031(19) Uani 1 1 d . . . . .
H33 H 0.457709 0.614824 0.312258 0.124 Uiso 1 1 calc R U . . .
C34 C 0.4214(3) 0.6811(3) 0.2376(4) 0.1029(19) Uani 1 1 d . . . . .
H34 H 0.429119 0.668800 0.167949 0.123 Uiso 1 1 calc R U . . .
C35 C 0.3936(2) 0.7313(3) 0.2546(4) 0.0845(15) Uani 1 1 d . . . . .
H35 H 0.382624 0.753705 0.196225 0.101 Uiso 1 1 calc R U . . .
C36 C 0.38134(16) 0.74988(19) 0.3589(3) 0.0628(10) Uani 1 1 d . . . . .
H36 H 0.362294 0.784545 0.369332 0.075 Uiso 1 1 calc R U . . .
C41 C 0.33845(14) 0.69469(13) 0.6069(3) 0.0484(7) Uani 1 1 d . . . . .
C42 C 0.35293(19) 0.64171(15) 0.6521(3) 0.0595(9) Uani 1 1 d . . . . .
H42 H 0.391310 0.632341 0.663119 0.071 Uiso 1 1 calc R U . . .
C43 C 0.3102(3) 0.60300(18) 0.6806(3) 0.0804(14) Uani 1 1 d . . . . .
H43 H 0.319999 0.567751 0.710623 0.096 Uiso 1 1 calc R U . . .
C44 C 0.2526(2) 0.6170(2) 0.6641(4) 0.0819(15) Uani 1 1 d . . . . .
H44 H 0.224008 0.590994 0.682951 0.098 Uiso 1 1 calc R U . . .
C45 C 0.23831(19) 0.6684(2) 0.6206(4) 0.0752(12) Uani 1 1 d . . . . .
H45 H 0.199869 0.677713 0.610142 0.090 Uiso 1 1 calc R U . . .
C46 C 0.28086(15) 0.70729(17) 0.5916(3) 0.0561(8) Uani 1 1 d . . . . .
H46 H 0.270519 0.742352 0.561445 0.067 Uiso 1 1 calc R U . . .
C51 C 0.54040(12) 0.79842(12) 0.7258(2) 0.0395(6) Uani 1 1 d . . . . .
C52 C 0.54468(12) 0.76358(13) 0.6355(2) 0.0418(6) Uani 1 1 d . . . . .
C53 C 0.59336(14) 0.73046(15) 0.6186(3) 0.0524(7) Uani 1 1 d . . . . .
H53 H 0.595997 0.706197 0.559335 0.063 Uiso 1 1 calc R U . . .
C54 C 0.63799(15) 0.73438(18) 0.6920(3) 0.0610(9) Uani 1 1 d . . . . .
H54 H 0.670999 0.712647 0.681139 0.073 Uiso 1 1 calc R U . . .
C55 C 0.63464(14) 0.76939(17) 0.7799(3) 0.0571(8) Uani 1 1 d . . . . .
H55 H 0.665254 0.771251 0.827847 0.069 Uiso 1 1 calc R U . . .
C56 C 0.58540(14) 0.80252(15) 0.7984(3) 0.0487(7) Uani 1 1 d . . . . .
H56 H 0.582975 0.826664 0.857821 0.058 Uiso 1 1 calc R U . . .
C61 C 0.47307(12) 0.86006(12) 0.6335(3) 0.0423(6) Uani 1 1 d . . . . .
C62 C 0.47962(12) 0.82728(13) 0.5400(3) 0.0433(6) Uani 1 1 d . . . . .
C63 C 0.47316(14) 0.85254(17) 0.4394(3) 0.0562(8) Uani 1 1 d . . . . .
H63 H 0.478203 0.830979 0.377106 0.067 Uiso 1 1 calc R U . . .
C64 C 0.45911(19) 0.9102(2) 0.4332(4) 0.0734(12) Uani 1 1 d . . . . .
H64 H 0.454953 0.927501 0.366149 0.088 Uiso 1 1 calc R U . . .
C65 C 0.45122(18) 0.94229(17) 0.5253(4) 0.0723(12) Uani 1 1 d . . . . .
H65 H 0.440774 0.980730 0.519815 0.087 Uiso 1 1 calc R U . . .
C66 C 0.45871(14) 0.91780(14) 0.6258(3) 0.0552(8) Uani 1 1 d . . . . .
H66 H 0.454166 0.939820 0.687650 0.066 Uiso 1 1 calc R U . . .
Cl1 Cl 0.4891(4) 0.4198(5) 0.6099(13) 0.218(5) Uani 0.3333 1 d D U P A -1
Cl2 Cl 0.5284(10) 0.5114(14) 0.956(2) 0.401(18) Uani 0.3333 1 d D U P A -1
C71 C 0.4962(5) 0.4718(6) 0.6751(12) 0.129(6) Uani 0.3333 1 d DG U P A -1
C72 C 0.5065(6) 0.4668(6) 0.7849(13) 0.167(8) Uani 0.3333 1 d DG U P A -1
H72 H 0.509590 0.430660 0.816219 0.200 Uiso 0.3333 1 calc R U P A -1
C73 C 0.5120(8) 0.5158(8) 0.8479(12) 0.189(9) Uani 0.3333 1 d DG U P A -1
C74 C 0.5073(8) 0.5698(6) 0.8011(15) 0.143(7) Uani 0.3333 1 d DG U P A -1
H74 H 0.511081 0.602632 0.843292 0.172 Uiso 0.3333 1 calc R U P A -1
C75 C 0.4971(9) 0.5749(6) 0.6913(16) 0.161(8) Uani 0.3333 1 d G U P A -1
H75 H 0.493954 0.610998 0.660039 0.193 Uiso 0.3333 1 calc R U P A -1
C76 C 0.4915(8) 0.5258(7) 0.6283(12) 0.139(6) Uani 0.3333 1 d DG U P A -1
H76 H 0.484646 0.529196 0.554875 0.166 Uiso 0.3333 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C1 1.426(4) . ?
O1 H1A 0.8200 . ?
O2 C4 1.432(4) . ?
O2 H2A 0.8200 . ?
C1 C21 1.540(4) . ?
C1 C11 1.543(4) . ?
C1 C2 1.569(4) . ?
C2 C3 1.571(4) . ?
C2 C5 1.581(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.573(4) . ?
C3 C6 1.573(4) . ?
C3 H3 0.9800 . ?
C4 C41 1.547(4) . ?
C4 C31 1.551(5) . ?
C5 C61 1.491(4) . ?
C5 C51 1.523(4) . ?
C5 H5 0.9800 . ?
C6 C52 1.509(4) . ?
C6 C62 1.512(4) . ?
C6 H6 0.9800 . ?
C11 C16 1.386(5) . ?
C11 C12 1.402(5) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.357(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.377(5) . ?
C21 C22 1.390(5) . ?
C22 C23 1.383(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.348(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.390(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C31 C32 1.370(6) . ?
C31 C36 1.390(5) . ?
C32 C33 1.393(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.360(10) . ?
C33 H33 0.9300 . ?
C34 C35 1.351(9) . ?
C34 H34 0.9300 . ?
C35 C36 1.396(7) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C41 C46 1.386(5) . ?
C41 C42 1.396(5) . ?
C42 C43 1.388(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.395(8) . ?
C43 H43 0.9300 . ?
C44 C45 1.355(8) . ?
C44 H44 0.9300 . ?
C45 C46 1.390(5) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C51 C56 1.386(4) . ?
C51 C52 1.388(4) . ?
C52 C53 1.387(4) . ?
C53 C54 1.386(5) . ?
C53 H53 0.9300 . ?
C54 C55 1.365(6) . ?
C54 H54 0.9300 . ?
C55 C56 1.401(5) . ?
C55 H55 0.9300 . ?
C56 H56 0.9300 . ?
C61 C66 1.389(4) . ?
C61 C62 1.398(5) . ?
C62 C63 1.390(5) . ?
C63 C64 1.384(6) . ?
C63 H63 0.9300 . ?
C64 C65 1.379(7) . ?
C64 H64 0.9300 . ?
C65 C66 1.384(6) . ?
C65 H65 0.9300 . ?
C66 H66 0.9300 . ?
Cl1 C71 1.467(16) . ?
Cl2 C73 1.40(2) . ?
C71 C72 1.3900 . ?
C71 C76 1.3900 . ?
C72 C73 1.3900 . ?
C72 H72 0.9300 . ?
C73 C74 1.3900 . ?
C74 C75 1.3900 . ?
C74 H74 0.9300 . ?
C75 C76 1.3900 . ?
C75 H75 0.9300 . ?
C76 H76 0.9300 . ?

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 105.7(2) . . ?
O1 C1 C11 110.8(3) . . ?
C21 C1 C11 104.2(2) . . ?
O1 C1 C2 110.7(2) . . ?
C21 C1 C2 114.8(2) . . ?
C11 C1 C2 110.4(2) . . ?
C1 C2 C3 115.6(2) . . ?
C1 C2 C5 110.4(2) . . ?
C3 C2 C5 108.3(2) . . ?
C1 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
C5 C2 H2 107.4 . . ?
C2 C3 C4 114.5(2) . . ?
C2 C3 C6 108.7(2) . . ?
C4 C3 C6 111.1(2) . . ?
C2 C3 H3 107.4 . . ?
C4 C3 H3 107.4 . . ?
C6 C3 H3 107.4 . . ?
O2 C4 C41 105.1(2) . . ?
O2 C4 C31 109.2(3) . . ?
C41 C4 C31 105.5(2) . . ?
O2 C4 C3 110.3(2) . . ?
C41 C4 C3 114.9(2) . . ?
C31 C4 C3 111.4(2) . . ?
C61 C5 C51 106.5(2) . . ?
C61 C5 C2 107.4(2) . . ?
C51 C5 C2 108.1(2) . . ?
C61 C5 H5 111.5 . . ?
C51 C5 H5 111.5 . . ?
C2 C5 H5 111.5 . . ?
C52 C6 C62 107.1(2) . . ?
C52 C6 C3 107.2(2) . . ?
C62 C6 C3 107.7(2) . . ?
C52 C6 H6 111.5 . . ?
C62 C6 H6 111.5 . . ?
C3 C6 H6 111.5 . . ?
C16 C11 C12 117.3(3) . . ?
C16 C11 C1 121.6(3) . . ?
C12 C11 C1 121.0(3) . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.9(5) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.8(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.6(5) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 121.0(5) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C26 C21 C22 117.6(3) . . ?
C26 C21 C1 122.5(3) . . ?
C22 C21 C1 119.6(3) . . ?
C23 C22 C21 120.9(4) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 120.3(4) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 119.1(4) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 121.1(4) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C21 C26 C25 121.0(4) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C32 C31 C36 117.8(4) . . ?
C32 C31 C4 121.0(3) . . ?
C36 C31 C4 121.2(3) . . ?
C31 C32 C33 120.7(5) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C34 C33 C32 121.0(6) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C35 C34 C33 119.2(5) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C36 120.7(5) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C31 C36 C35 120.5(5) . . ?
C31 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C46 C41 C42 118.4(3) . . ?
C46 C41 C4 118.9(3) . . ?
C42 C41 C4 122.4(3) . . ?
C43 C42 C41 120.2(4) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C42 C43 C44 120.0(4) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C45 C44 C43 120.1(4) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 120.2(5) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C41 C46 C45 121.1(4) . . ?
C41 C46 H46 119.5 . . ?
C45 C46 H46 119.5 . . ?
C56 C51 C52 120.8(3) . . ?
C56 C51 C5 126.8(3) . . ?
C52 C51 C5 112.3(2) . . ?
C53 C52 C51 120.4(3) . . ?
C53 C52 C6 125.9(3) . . ?
C51 C52 C6 113.6(2) . . ?
C54 C53 C52 118.4(3) . . ?
C54 C53 H53 120.8 . . ?
C52 C53 H53 120.8 . . ?
C55 C54 C53 121.6(3) . . ?
C55 C54 H54 119.2 . . ?
C53 C54 H54 119.2 . . ?
C54 C55 C56 120.4(3) . . ?
C54 C55 H55 119.8 . . ?
C56 C55 H55 119.8 . . ?
C51 C56 C55 118.3(3) . . ?
C51 C56 H56 120.8 . . ?
C55 C56 H56 120.8 . . ?
C66 C61 C62 119.9(3) . . ?
C66 C61 C5 126.3(3) . . ?
C62 C61 C5 113.9(2) . . ?
C63 C62 C61 120.3(3) . . ?
C63 C62 C6 127.6(3) . . ?
C61 C62 C6 112.1(3) . . ?
C64 C63 C62 119.1(4) . . ?
C64 C63 H63 120.5 . . ?
C62 C63 H63 120.5 . . ?
C65 C64 C63 120.7(4) . . ?
C65 C64 H64 119.7 . . ?
C63 C64 H64 119.7 . . ?
C64 C65 C66 120.6(3) . . ?
C64 C65 H65 119.7 . . ?
C66 C65 H65 119.7 . . ?
C65 C66 C61 119.4(4) . . ?
C65 C66 H66 120.3 . . ?
C61 C66 H66 120.3 . . ?
C72 C71 C76 120.0 . . ?
C72 C71 Cl1 119.5(9) . . ?
C76 C71 Cl1 120.5(9) . . ?
C71 C72 C73 120.0 . . ?
C71 C72 H72 120.0 . . ?
C73 C72 H72 120.0 . . ?
C74 C73 C72 120.0 . . ?
C74 C73 Cl2 119.3(11) . . ?
C72 C73 Cl2 120.4(11) . . ?
C73 C74 C75 120.0 . . ?
C73 C74 H74 120.0 . . ?
C75 C74 H74 120.0 . . ?
C74 C75 C76 120.0 . . ?
C74 C75 H75 120.0 . . ?
C76 C75 H75 120.0 . . ?
C75 C76 C71 120.0 . . ?
C75 C76 H76 120.0 . . ?
C71 C76 H76 120.0 . . ?

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 44.9(3) . . . . ?
C21 C1 C2 C3 -74.7(3) . . . . ?
C11 C1 C2 C3 168.0(2) . . . . ?
O1 C1 C2 C5 -78.5(3) . . . . ?
C21 C1 C2 C5 162.0(2) . . . . ?
C11 C1 C2 C5 44.7(3) . . . . ?
C1 C2 C3 C4 112.0(3) . . . . ?
C5 C2 C3 C4 -123.5(2) . . . . ?
C1 C2 C3 C6 -123.1(2) . . . . ?
C5 C2 C3 C6 1.4(3) . . . . ?
C2 C3 C4 O2 40.6(3) . . . . ?
C6 C3 C4 O2 -83.0(3) . . . . ?
C2 C3 C4 C41 -78.0(3) . . . . ?
C6 C3 C4 C41 158.4(2) . . . . ?
C2 C3 C4 C31 162.1(2) . . . . ?
C6 C3 C4 C31 38.5(3) . . . . ?
C1 C2 C5 C61 -175.9(2) . . . . ?
C3 C2 C5 C61 56.6(3) . . . . ?
C1 C2 C5 C51 69.5(3) . . . . ?
C3 C2 C5 C51 -58.0(3) . . . . ?
C2 C3 C6 C52 56.7(3) . . . . ?
C4 C3 C6 C52 -176.4(2) . . . . ?
C2 C3 C6 C62 -58.2(3) . . . . ?
C4 C3 C6 C62 68.6(3) . . . . ?
O1 C1 C11 C16 -6.8(4) . . . . ?
C21 C1 C11 C16 106.4(3) . . . . ?
C2 C1 C11 C16 -129.8(3) . . . . ?
O1 C1 C11 C12 173.6(3) . . . . ?
C21 C1 C11 C12 -73.2(4) . . . . ?
C2 C1 C11 C12 50.5(4) . . . . ?
C16 C11 C12 C13 0.5(5) . . . . ?
C1 C11 C12 C13 -179.8(3) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C12 C13 C14 C15 0.3(7) . . . . ?
C13 C14 C15 C16 -0.5(7) . . . . ?
C14 C15 C16 C11 0.8(7) . . . . ?
C12 C11 C16 C15 -0.8(5) . . . . ?
C1 C11 C16 C15 179.5(4) . . . . ?
O1 C1 C21 C26 -161.2(3) . . . . ?
C11 C1 C21 C26 81.9(4) . . . . ?
C2 C1 C21 C26 -38.9(4) . . . . ?
O1 C1 C21 C22 25.1(4) . . . . ?
C11 C1 C21 C22 -91.8(4) . . . . ?
C2 C1 C21 C22 147.4(3) . . . . ?
C26 C21 C22 C23 0.3(6) . . . . ?
C1 C21 C22 C23 174.3(4) . . . . ?
C21 C22 C23 C24 0.0(8) . . . . ?
C22 C23 C24 C25 -0.5(8) . . . . ?
C23 C24 C25 C26 0.7(7) . . . . ?
C22 C21 C26 C25 -0.1(5) . . . . ?
C1 C21 C26 C25 -173.9(3) . . . . ?
C24 C25 C26 C21 -0.4(6) . . . . ?
O2 C4 C31 C32 178.8(3) . . . . ?
C41 C4 C31 C32 -68.6(4) . . . . ?
C3 C4 C31 C32 56.7(4) . . . . ?
O2 C4 C31 C36 -1.0(4) . . . . ?
C41 C4 C31 C36 111.5(3) . . . . ?
C3 C4 C31 C36 -123.2(3) . . . . ?
C36 C31 C32 C33 0.9(7) . . . . ?
C4 C31 C32 C33 -178.9(5) . . . . ?
C31 C32 C33 C34 -1.7(10) . . . . ?
C32 C33 C34 C35 1.5(10) . . . . ?
C33 C34 C35 C36 -0.6(8) . . . . ?
C32 C31 C36 C35 0.0(5) . . . . ?
C4 C31 C36 C35 179.8(3) . . . . ?
C34 C35 C36 C31 -0.1(6) . . . . ?
O2 C4 C41 C46 25.6(4) . . . . ?
C31 C4 C41 C46 -89.8(3) . . . . ?
C3 C4 C41 C46 147.1(3) . . . . ?
O2 C4 C41 C42 -160.4(3) . . . . ?
C31 C4 C41 C42 84.2(4) . . . . ?
C3 C4 C41 C42 -38.9(4) . . . . ?
C46 C41 C42 C43 0.0(5) . . . . ?
C4 C41 C42 C43 -174.0(3) . . . . ?
C41 C42 C43 C44 0.0(6) . . . . ?
C42 C43 C44 C45 -0.2(7) . . . . ?
C43 C44 C45 C46 0.4(7) . . . . ?
C42 C41 C46 C45 0.2(5) . . . . ?
C4 C41 C46 C45 174.4(3) . . . . ?
C44 C45 C46 C41 -0.4(6) . . . . ?
C61 C5 C51 C56 125.6(3) . . . . ?
C2 C5 C51 C56 -119.2(3) . . . . ?
C61 C5 C51 C52 -57.3(3) . . . . ?
C2 C5 C51 C52 57.9(3) . . . . ?
C56 C51 C52 C53 2.5(5) . . . . ?
C5 C51 C52 C53 -174.8(3) . . . . ?
C56 C51 C52 C6 -179.2(3) . . . . ?
C5 C51 C52 C6 3.4(4) . . . . ?
C62 C6 C52 C53 -129.0(3) . . . . ?
C3 C6 C52 C53 115.6(3) . . . . ?
C62 C6 C52 C51 52.9(3) . . . . ?
C3 C6 C52 C51 -62.5(3) . . . . ?
C51 C52 C53 C54 -1.9(5) . . . . ?
C6 C52 C53 C54 -179.9(3) . . . . ?
C52 C53 C54 C55 0.6(6) . . . . ?
C53 C54 C55 C56 0.1(6) . . . . ?
C52 C51 C56 C55 -1.8(5) . . . . ?
C5 C51 C56 C55 175.1(3) . . . . ?
C54 C55 C56 C51 0.5(5) . . . . ?
C51 C5 C61 C66 -127.0(3) . . . . ?
C2 C5 C61 C66 117.3(3) . . . . ?
C51 C5 C61 C62 54.2(3) . . . . ?
C2 C5 C61 C62 -61.5(3) . . . . ?
C66 C61 C62 C63 1.5(4) . . . . ?
C5 C61 C62 C63 -179.6(3) . . . . ?
C66 C61 C62 C6 -176.9(3) . . . . ?
C5 C61 C62 C6 2.0(3) . . . . ?
C52 C6 C62 C63 125.7(3) . . . . ?
C3 C6 C62 C63 -119.2(3) . . . . ?
C52 C6 C62 C61 -56.0(3) . . . . ?
C3 C6 C62 C61 59.1(3) . . . . ?
C61 C62 C63 C64 -1.2(4) . . . . ?
C6 C62 C63 C64 177.0(3) . . . . ?
C62 C63 C64 C65 -0.4(5) . . . . ?
C63 C64 C65 C66 1.7(6) . . . . ?
C64 C65 C66 C61 -1.4(5) . . . . ?
C62 C61 C66 C65 -0.2(5) . . . . ?
C5 C61 C66 C65 -179.0(3) . . . . ?
C76 C71 C72 C73 0.0 . . . . ?
Cl1 C71 C72 C73 -178.6(6) . . . . ?
C71 C72 C73 C74 0.0 . . . . ?
C71 C72 C73 Cl2 -173.2(18) . . . . ?
C72 C73 C74 C75 0.0 . . . . ?
Cl2 C73 C74 C75 173.3(18) . . . . ?
C73 C74 C75 C76 0.0 . . . . ?
C74 C75 C76 C71 0.0 . . . . ?
C72 C71 C76 C75 0.0 . . . . ?
Cl1 C71 C76 C75 178.6(6) . . . . ?

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 0.98 2.38 2.887(4) 111 . yes
C3 H3 O1 0.98 2.48 2.946(4) 109 . yes
C16 H16 O1 0.93 2.43 2.785(5) 103 . yes
C22 H22 O1 0.93 2.32 2.676(5) 102 . yes
C32 H32 Cl1^a 0.93 3.32 3.650(10) 103 3_566 yes
C36 H36 O2 0.93 2.38 2.748(5) 103 . yes
C46 H46 O2 0.93 2.30 2.658(4) 103 . yes

_refine_diff_density_max         0.515
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: m-dichlorobenzene'
