# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ja169
_database_code_depnum_ccdc_archive 'CCDC 2088998'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
α,α-Bis(p-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11-methanol
;
_chemical_name_common            ?
_chemical_melting_point          397.15
_chemical_formula_moiety         'C29 H22 Cl2 O, C8 H10'
_chemical_formula_sum            'C37 H32 Cl2 O'
_chemical_formula_weight         563.52

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.760(4)
_cell_length_b                   10.850(4)
_cell_length_c                   15.146(5)
_cell_angle_alpha                98.370(17)
_cell_angle_beta                 96.251(17)
_cell_angle_gamma                103.375(17)
_cell_volume                     1526.7(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6952
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.09

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    0.240
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9521
_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            21529
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.960
_diffrn_reflns_theta_max         28.467
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7515
_reflns_number_gt                4946
_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       '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          
;
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 disordered methyl groups were placed in calculated positions
and were included in the refinement in the riding model approximation, with
Uiso(H) set to 1.5 Ueq(C).

The H atom of the hydroxyl group was allowed to rotate with a fixed angle around
the C---O bond 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 0-xylene is extensively disordered necessitating the use of various
constraints and restraints such as RIGU, EADP and ISOR. The phenyl ring was
forced into a regular hexagon with bond lengths 1.39 Å (AFIX 66 in the SHELXL
program (Sheldrick, 2015)).

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0727P)²+0.3633P] 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         7515
_refine_ls_number_parameters     369
_refine_ls_number_restraints     124
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1610
_refine_ls_wR_factor_gt          0.1425
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.054
_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
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


_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 1.741(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_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_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) . . . . ?

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

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_ja166
_database_code_depnum_ccdc_archive 'CCDC 2089000'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
α,α-Bis(p-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11-methanol
;
_chemical_name_common            ?
_chemical_melting_point          397.15
_chemical_formula_moiety         'C29 H22 Cl2 O, C8 H10'
_chemical_formula_sum            'C37 H32 Cl2 O'
_chemical_formula_weight         563.52

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.3172(19)
_cell_length_b                   12.742(2)
_cell_length_c                   13.082(2)
_cell_angle_alpha                67.795(9)
_cell_angle_beta                 71.424(8)
_cell_angle_gamma                72.877(9)
_cell_volume                     1479.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9681
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.623
_exptl_crystal_size_mid          0.474
_exptl_crystal_size_min          0.172
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9232
_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            61561
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.729
_diffrn_reflns_theta_max         28.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7386
_reflns_number_gt                5264
_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       '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          
;
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 methyl groups were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(C).

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.4863P] 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         7386
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
Cl1 Cl 0.46512(7) 0.13540(4) 0.86143(5) 0.07917(19) Uani 1 1 d . . . . .
Cl2 Cl 0.72042(8) 0.87403(6) 0.36528(6) 0.0985(2) Uani 1 1 d . . . . .
O1 O 0.37121(13) 0.65424(10) 0.89734(10) 0.0511(3) Uani 1 1 d . . . . .
H1 H 0.319712 0.710266 0.915466 0.077 Uiso 1 1 calc R U . . .
C1 C 0.33639(16) 0.64645(13) 0.80364(12) 0.0388(3) Uani 1 1 d . . . . .
C2 C 0.18250(15) 0.70480(12) 0.79990(12) 0.0377(3) Uani 1 1 d . . . . .
H2 H 0.166984 0.698014 0.732739 0.045 Uiso 1 1 calc R U . . .
C3 C 0.14894(17) 0.83728(12) 0.78564(13) 0.0413(3) Uani 1 1 d . . . . .
H3 H 0.218090 0.877964 0.724285 0.050 Uiso 1 1 calc R U . . .
C4 C 0.07456(18) 0.64617(13) 0.90363(13) 0.0460(4) Uani 1 1 d . . . . .
H4A H 0.121096 0.593626 0.963204 0.055 Uiso 1 1 calc R U . . .
H4B H 0.032422 0.601621 0.881730 0.055 Uiso 1 1 calc R U . . .
C5 C -0.04071(18) 0.73919(14) 0.94885(13) 0.0495(4) Uani 1 1 d . . . . .
H5 H -0.114089 0.704986 1.011171 0.059 Uiso 1 1 calc R U . . .
C11 C 0.36421(15) 0.51669(12) 0.81934(12) 0.0385(3) Uani 1 1 d . . . . .
C12 C 0.30325(17) 0.47240(13) 0.76779(13) 0.0445(3) Uani 1 1 d . . . . .
H12 H 0.240616 0.522237 0.724239 0.053 Uiso 1 1 calc R U . . .
C13 C 0.33404(17) 0.35559(14) 0.78009(14) 0.0463(4) Uani 1 1 d . . . . .
H13 H 0.292789 0.327065 0.745040 0.056 Uiso 1 1 calc R U . . .
C14 C 0.42637(18) 0.28231(13) 0.84479(14) 0.0469(4) Uani 1 1 d . . . . .
C15 C 0.48811(19) 0.32316(15) 0.89715(15) 0.0519(4) Uani 1 1 d . . . . .
H15 H 0.550355 0.272704 0.940795 0.062 Uiso 1 1 calc R U . . .
C16 C 0.45678(17) 0.44008(14) 0.88429(13) 0.0460(4) Uani 1 1 d . . . . .
H16 H 0.498401 0.467834 0.919749 0.055 Uiso 1 1 calc R U . . .
C21 C 0.43393(16) 0.70481(13) 0.69245(13) 0.0409(3) Uani 1 1 d . . . . .
C22 C 0.4242(2) 0.70722(18) 0.58874(15) 0.0580(5) Uani 1 1 d . . . . .
H22 H 0.358401 0.672024 0.586558 0.070 Uiso 1 1 calc R U . . .
C23 C 0.5097(2) 0.76052(19) 0.48800(16) 0.0643(5) Uani 1 1 d . . . . .
H23 H 0.500442 0.762079 0.418997 0.077 Uiso 1 1 calc R U . . .
C24 C 0.6081(2) 0.81095(16) 0.49095(17) 0.0589(5) Uani 1 1 d . . . . .
C25 C 0.6201(2) 0.8106(2) 0.59168(19) 0.0717(6) Uani 1 1 d . . . . .
H25 H 0.686519 0.845707 0.593103 0.086 Uiso 1 1 calc R U . . .
C26 C 0.5333(2) 0.75773(17) 0.69209(17) 0.0605(5) Uani 1 1 d . . . . .
H26 H 0.542076 0.757902 0.760603 0.073 Uiso 1 1 calc R U . . .
C31 C 0.13646(19) 0.85208(13) 0.89804(14) 0.0480(4) Uani 1 1 d . . . . .
C32 C 0.0332(2) 0.80025(14) 0.98544(14) 0.0516(4) Uani 1 1 d . . . . .
C33 C 0.0085(2) 0.80748(18) 1.09302(16) 0.0685(6) Uani 1 1 d . . . . .
H33 H -0.060804 0.773673 1.151418 0.082 Uiso 1 1 calc R U . . .
C34 C 0.0871(3) 0.8651(2) 1.1134(2) 0.0823(8) Uani 1 1 d . . . . .
H34 H 0.070591 0.869663 1.185856 0.099 Uiso 1 1 calc R U . . .
C35 C 0.1893(3) 0.91579(18) 1.0279(2) 0.0783(7) Uani 1 1 d . . . . .
H35 H 0.241460 0.954157 1.043159 0.094 Uiso 1 1 calc R U . . .
C36 C 0.2157(2) 0.91032(15) 0.91867(18) 0.0613(5) Uani 1 1 d . . . . .
H36 H 0.284810 0.944821 0.860672 0.074 Uiso 1 1 calc R U . . .
C41 C 0.00444(17) 0.88074(13) 0.76213(13) 0.0429(3) Uani 1 1 d . . . . .
C42 C -0.09776(17) 0.82683(14) 0.84988(14) 0.0468(4) Uani 1 1 d . . . . .
C43 C -0.23471(19) 0.85620(17) 0.83969(17) 0.0573(4) Uani 1 1 d . . . . .
H43 H -0.302523 0.819981 0.897628 0.069 Uiso 1 1 calc R U . . .
C44 C -0.2698(2) 0.93959(18) 0.74297(18) 0.0630(5) Uani 1 1 d . . . . .
H44 H -0.361631 0.960055 0.736058 0.076 Uiso 1 1 calc R U . . .
C45 C -0.1691(2) 0.99236(16) 0.65693(17) 0.0616(5) Uani 1 1 d . . . . .
H45 H -0.193603 1.048251 0.592052 0.074 Uiso 1 1 calc R U . . .
C46 C -0.0315(2) 0.96331(14) 0.66562(15) 0.0516(4) Uani 1 1 d . . . . .
H46 H 0.035896 0.999229 0.606861 0.062 Uiso 1 1 calc R U . . .
C51 C 0.8301(2) 0.4029(2) 0.50655(19) 0.0734(6) Uani 1 1 d . . . . .
C52 C 0.9166(2) 0.3173(2) 0.4628(2) 0.0726(6) Uani 1 1 d . . . . .
H52 H 0.902109 0.241846 0.498217 0.087 Uiso 1 1 calc R U . . .
C53 C 1.0241(2) 0.34034(19) 0.36794(19) 0.0674(5) Uani 1 1 d . . . . .
H53 H 1.079987 0.280578 0.339893 0.081 Uiso 1 1 calc R U . . .
C54 C 1.0500(2) 0.45071(19) 0.31401(17) 0.0647(5) Uani 1 1 d . . . . .
C55 C 0.9628(3) 0.53648(18) 0.3586(2) 0.0702(6) Uani 1 1 d . . . . .
H55 H 0.977719 0.611853 0.324207 0.084 Uiso 1 1 calc R U . . .
C56 C 0.8552(2) 0.5132(2) 0.4520(2) 0.0740(6) Uani 1 1 d . . . . .
H56 H 0.797803 0.573170 0.479145 0.089 Uiso 1 1 calc R U . . .
C57 C 0.7136(3) 0.3767(4) 0.6113(3) 0.1265(13) Uani 1 1 d . . . . .
H57A H 0.627826 0.427887 0.596149 0.190 Uiso 1 1 calc R U . . .
H57B H 0.734448 0.387563 0.672714 0.190 Uiso 1 1 calc R U . . .
H57C H 0.704334 0.298126 0.631789 0.190 Uiso 1 1 calc R U . . .
C58 C 1.1708(3) 0.4754(3) 0.2123(2) 0.1021(9) Uani 1 1 d . . . . .
H58A H 1.187073 0.423435 0.170194 0.153 Uiso 1 1 calc R U . . .
H58B H 1.252959 0.464855 0.237435 0.153 Uiso 1 1 calc R U . . .
H58C H 1.149220 0.553715 0.164539 0.153 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 1.7372(16) . ?
Cl2 C24 1.7401(19) . ?
O1 C1 1.4266(17) . ?
O1 H1 0.8200 . ?
C1 C11 1.536(2) . ?
C1 C21 1.540(2) . ?
C1 C2 1.550(2) . ?
C2 C4 1.549(2) . ?
C2 C3 1.569(2) . ?
C2 H2 0.9800 . ?
C3 C31 1.513(2) . ?
C3 C41 1.517(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.556(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C42 1.509(2) . ?
C5 C32 1.510(3) . ?
C5 H5 0.9800 . ?
C11 C16 1.389(2) . ?
C11 C12 1.391(2) . ?
C12 C13 1.384(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(2) . ?
C15 C16 1.383(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C22 1.380(2) . ?
C21 C26 1.381(2) . ?
C22 C23 1.382(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.360(3) . ?
C25 C26 1.385(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C31 C36 1.393(2) . ?
C31 C32 1.395(3) . ?
C32 C33 1.382(2) . ?
C33 C34 1.380(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.372(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.392(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C41 C46 1.380(2) . ?
C41 C42 1.400(2) . ?
C42 C43 1.387(3) . ?
C43 C44 1.382(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.376(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.389(3) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C51 C52 1.373(3) . ?
C51 C56 1.375(3) . ?
C51 C57 1.509(3) . ?
C52 C53 1.377(3) . ?
C52 H52 0.9300 . ?
C53 C54 1.378(3) . ?
C53 H53 0.9300 . ?
C54 C55 1.383(3) . ?
C54 C58 1.511(3) . ?
C55 C56 1.367(3) . ?
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 . ?

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 105.85(11) . . ?
O1 C1 C21 109.22(12) . . ?
C11 C1 C21 108.91(12) . . ?
O1 C1 C2 111.41(12) . . ?
C11 C1 C2 111.68(12) . . ?
C21 C1 C2 109.67(12) . . ?
C4 C2 C1 114.02(12) . . ?
C4 C2 C3 108.49(12) . . ?
C1 C2 C3 113.38(12) . . ?
C4 C2 H2 106.8 . . ?
C1 C2 H2 106.8 . . ?
C3 C2 H2 106.8 . . ?
C31 C3 C41 106.70(13) . . ?
C31 C3 C2 109.06(12) . . ?
C41 C3 C2 104.56(12) . . ?
C31 C3 H3 112.0 . . ?
C41 C3 H3 112.0 . . ?
C2 C3 H3 112.0 . . ?
C2 C4 C5 110.17(12) . . ?
C2 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C2 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C42 C5 C32 107.03(14) . . ?
C42 C5 C4 107.62(13) . . ?
C32 C5 C4 105.89(14) . . ?
C42 C5 H5 112.0 . . ?
C32 C5 H5 112.0 . . ?
C4 C5 H5 112.0 . . ?
C16 C11 C12 118.06(14) . . ?
C16 C11 C1 119.45(13) . . ?
C12 C11 C1 122.46(13) . . ?
C13 C12 C11 121.25(15) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 119.12(15) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.11(15) . . ?
C13 C14 Cl1 119.53(13) . . ?
C15 C14 Cl1 119.37(13) . . ?
C14 C15 C16 119.36(15) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C11 121.10(15) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C22 C21 C26 117.31(16) . . ?
C22 C21 C1 121.05(14) . . ?
C26 C21 C1 121.64(14) . . ?
C21 C22 C23 121.82(16) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C24 C23 C22 119.27(18) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C25 C24 C23 120.45(17) . . ?
C25 C24 Cl2 119.73(15) . . ?
C23 C24 Cl2 119.81(16) . . ?
C24 C25 C26 119.85(17) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 121.29(17) . . ?
C21 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C36 C31 C32 120.44(17) . . ?
C36 C31 C3 126.45(17) . . ?
C32 C31 C3 113.11(14) . . ?
C33 C32 C31 119.82(19) . . ?
C33 C32 C5 126.70(18) . . ?
C31 C32 C5 113.48(14) . . ?
C34 C33 C32 119.7(2) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C35 C34 C33 120.82(19) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C34 C35 C36 120.6(2) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C35 C36 C31 118.6(2) . . ?
C35 C36 H36 120.7 . . ?
C31 C36 H36 120.7 . . ?
C46 C41 C42 119.79(16) . . ?
C46 C41 C3 126.71(15) . . ?
C42 C41 C3 113.48(14) . . ?
C43 C42 C41 120.10(16) . . ?
C43 C42 C5 127.06(16) . . ?
C41 C42 C5 112.84(15) . . ?
C44 C43 C42 119.64(18) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C45 C44 C43 120.10(18) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C44 C45 C46 120.89(18) . . ?
C44 C45 H45 119.6 . . ?
C46 C45 H45 119.6 . . ?
C41 C46 C45 119.46(18) . . ?
C41 C46 H46 120.3 . . ?
C45 C46 H46 120.3 . . ?
C52 C51 C56 117.4(2) . . ?
C52 C51 C57 121.4(3) . . ?
C56 C51 C57 121.3(3) . . ?
C51 C52 C53 121.7(2) . . ?
C51 C52 H52 119.2 . . ?
C53 C52 H52 119.2 . . ?
C52 C53 C54 120.9(2) . . ?
C52 C53 H53 119.5 . . ?
C54 C53 H53 119.5 . . ?
C53 C54 C55 117.1(2) . . ?
C53 C54 C58 121.0(2) . . ?
C55 C54 C58 121.9(2) . . ?
C56 C55 C54 121.6(2) . . ?
C56 C55 H55 119.2 . . ?
C54 C55 H55 119.2 . . ?
C55 C56 C51 121.3(2) . . ?
C55 C56 H56 119.4 . . ?
C51 C56 H56 119.4 . . ?
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 . . ?
C54 C58 H58A 109.5 . . ?
C54 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C54 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?

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 -63.75(16) . . . . ?
C11 C1 C2 C4 54.38(16) . . . . ?
C21 C1 C2 C4 175.21(12) . . . . ?
O1 C1 C2 C3 61.07(16) . . . . ?
C11 C1 C2 C3 179.20(11) . . . . ?
C21 C1 C2 C3 -59.97(15) . . . . ?
C4 C2 C3 C31 51.38(17) . . . . ?
C1 C2 C3 C31 -76.37(16) . . . . ?
C4 C2 C3 C41 -62.43(15) . . . . ?
C1 C2 C3 C41 169.82(11) . . . . ?
C1 C2 C4 C5 134.57(14) . . . . ?
C3 C2 C4 C5 7.19(17) . . . . ?
C2 C4 C5 C42 52.49(18) . . . . ?
C2 C4 C5 C32 -61.71(16) . . . . ?
O1 C1 C11 C16 -22.93(19) . . . . ?
C21 C1 C11 C16 94.39(16) . . . . ?
C2 C1 C11 C16 -144.34(14) . . . . ?
O1 C1 C11 C12 159.13(14) . . . . ?
C21 C1 C11 C12 -83.55(17) . . . . ?
C2 C1 C11 C12 37.72(19) . . . . ?
C16 C11 C12 C13 -0.3(2) . . . . ?
C1 C11 C12 C13 177.65(14) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 Cl1 179.67(13) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
Cl1 C14 C15 C16 -179.72(13) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C12 C11 C16 C15 0.3(2) . . . . ?
C1 C11 C16 C15 -177.76(15) . . . . ?
O1 C1 C21 C22 178.65(15) . . . . ?
C11 C1 C21 C22 63.49(19) . . . . ?
C2 C1 C21 C22 -59.00(19) . . . . ?
O1 C1 C21 C26 -2.0(2) . . . . ?
C11 C1 C21 C26 -117.20(17) . . . . ?
C2 C1 C21 C26 120.31(17) . . . . ?
C26 C21 C22 C23 -0.2(3) . . . . ?
C1 C21 C22 C23 179.15(17) . . . . ?
C21 C22 C23 C24 0.9(3) . . . . ?
C22 C23 C24 C25 -1.2(3) . . . . ?
C22 C23 C24 Cl2 177.81(16) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
Cl2 C24 C25 C26 -178.30(17) . . . . ?
C22 C21 C26 C25 -0.3(3) . . . . ?
C1 C21 C26 C25 -179.65(18) . . . . ?
C24 C25 C26 C21 0.1(3) . . . . ?
C41 C3 C31 C36 -126.15(17) . . . . ?
C2 C3 C31 C36 121.44(17) . . . . ?
C41 C3 C31 C32 53.72(17) . . . . ?
C2 C3 C31 C32 -58.69(17) . . . . ?
C36 C31 C32 C33 0.5(2) . . . . ?
C3 C31 C32 C33 -179.34(15) . . . . ?
C36 C31 C32 C5 -178.98(15) . . . . ?
C3 C31 C32 C5 1.1(2) . . . . ?
C42 C5 C32 C33 124.88(18) . . . . ?
C4 C5 C32 C33 -120.51(18) . . . . ?
C42 C5 C32 C31 -55.64(18) . . . . ?
C4 C5 C32 C31 58.96(17) . . . . ?
C31 C32 C33 C34 -0.6(3) . . . . ?
C5 C32 C33 C34 178.87(18) . . . . ?
C32 C33 C34 C35 0.2(3) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
C34 C35 C36 C31 -0.2(3) . . . . ?
C32 C31 C36 C35 -0.2(3) . . . . ?
C3 C31 C36 C35 179.70(16) . . . . ?
C31 C3 C41 C46 125.90(17) . . . . ?
C2 C3 C41 C46 -118.62(16) . . . . ?
C31 C3 C41 C42 -55.17(16) . . . . ?
C2 C3 C41 C42 60.31(16) . . . . ?
C46 C41 C42 C43 0.1(2) . . . . ?
C3 C41 C42 C43 -178.90(14) . . . . ?
C46 C41 C42 C5 -179.90(14) . . . . ?
C3 C41 C42 C5 1.08(18) . . . . ?
C32 C5 C42 C43 -125.98(18) . . . . ?
C4 C5 C42 C43 120.58(18) . . . . ?
C32 C5 C42 C41 54.04(17) . . . . ?
C4 C5 C42 C41 -59.39(18) . . . . ?
C41 C42 C43 C44 -0.5(2) . . . . ?
C5 C42 C43 C44 179.48(16) . . . . ?
C42 C43 C44 C45 0.6(3) . . . . ?
C43 C44 C45 C46 -0.2(3) . . . . ?
C42 C41 C46 C45 0.3(2) . . . . ?
C3 C41 C46 C45 179.17(15) . . . . ?
C44 C45 C46 C41 -0.3(3) . . . . ?
C56 C51 C52 C53 -0.2(3) . . . . ?
C57 C51 C52 C53 -179.3(2) . . . . ?
C51 C52 C53 C54 0.8(3) . . . . ?
C52 C53 C54 C55 -0.7(3) . . . . ?
C52 C53 C54 C58 177.9(2) . . . . ?
C53 C54 C55 C56 -0.2(3) . . . . ?
C58 C54 C55 C56 -178.7(2) . . . . ?
C54 C55 C56 C51 0.8(3) . . . . ?
C52 C51 C56 C55 -0.6(3) . . . . ?
C57 C51 C56 C55 178.5(2) . . . . ?

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
C16 H16 O1 0.93 2.31 2.663(2) 102 . yes
C26 H26 O1 0.93 2.37 2.740(2) 103 . yes

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_ja167
_database_code_depnum_ccdc_archive 'CCDC 2088999'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
α,α-Bis(p-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11-methanol
;
_chemical_name_common            ?
_chemical_melting_point          397.15
_chemical_formula_moiety         'C29 H22 Cl2 O, C8 H10'
_chemical_formula_sum            'C37 H32 Cl2 O'
_chemical_formula_weight         563.52

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.830(3)
_cell_length_b                   10.658(3)
_cell_length_c                   15.343(4)
_cell_angle_alpha                96.197(10)
_cell_angle_beta                 96.104(11)
_cell_angle_gamma                105.604(11)
_cell_volume                     1523.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9776
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.493
_exptl_crystal_size_min          0.364
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8917
_exptl_absorpt_correction_T_max  0.9626
_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            59921
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.004
_diffrn_reflns_theta_max         28.444
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7345
_reflns_number_gt                4675
_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       '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          
;
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 methyl groups were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(C).

The H atom of the hydroxyl group was allowed to rotate with a fixed angle around
the C---O bond 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 molecule is disordered over two positions necessitating the use of
various constraints and restraints. The solvent phenyl ring was forced into a
regular hexagon with bond lengths 1.39 Å (AFIX 66 in the SHELXL program
(Sheldrick, 2015))
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0815P)²+0.1309P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7345
_refine_ls_number_parameters     416
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.061
_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
Cl1 Cl 0.61318(7) 0.13218(5) 0.33484(3) 0.0781(2) Uani 1 1 d . . . . .
Cl2 Cl 0.77429(7) 1.04811(7) 0.57451(4) 0.1011(2) Uani 1 1 d . . . . .
O1 O 0.70798(11) 0.69520(11) 0.17785(7) 0.0506(3) Uani 1 1 d . . . . .
H1 H 0.697210 0.755964 0.151924 0.076 Uiso 1 1 calc R U . . .
C1 C 0.60094(15) 0.66321(15) 0.23430(9) 0.0401(3) Uani 1 1 d . . . . .
C2 C 0.45352(15) 0.66466(13) 0.18699(8) 0.0368(3) Uani 1 1 d . . . . .
H2 H 0.383092 0.633887 0.226314 0.044 Uiso 1 1 calc R U . . .
C3 C 0.44365(15) 0.80359(13) 0.16778(9) 0.0388(3) Uani 1 1 d . . . . .
H3 H 0.476627 0.869544 0.220876 0.047 Uiso 1 1 calc R U . . .
C4 C 0.40722(17) 0.56814(13) 0.09870(9) 0.0428(3) Uani 1 1 d . . . . .
H4A H 0.331153 0.492008 0.105993 0.051 Uiso 1 1 calc R U . . .
H4B H 0.487212 0.538000 0.082795 0.051 Uiso 1 1 calc R U . . .
C5 C 0.35464(17) 0.63884(14) 0.02385(9) 0.0446(4) Uani 1 1 d . . . . .
H5 H 0.319603 0.579073 -0.032017 0.053 Uiso 1 1 calc R U . . .
C11 C 0.59884(15) 0.52640(14) 0.25724(9) 0.0402(3) Uani 1 1 d . . . . .
C12 C 0.71752(17) 0.48072(17) 0.24961(11) 0.0536(4) Uani 1 1 d . . . . .
H12 H 0.795512 0.532347 0.228142 0.064 Uiso 1 1 calc R U . . .
C13 C 0.7220(2) 0.36047(18) 0.27320(12) 0.0604(5) Uani 1 1 d . . . . .
H13 H 0.802698 0.331960 0.268221 0.073 Uiso 1 1 calc R U . . .
C14 C 0.60701(19) 0.28333(16) 0.30399(10) 0.0510(4) Uani 1 1 d . . . . .
C15 C 0.48730(19) 0.32449(16) 0.31170(11) 0.0534(4) Uani 1 1 d . . . . .
H15 H 0.409269 0.271686 0.332461 0.064 Uiso 1 1 calc R U . . .
C16 C 0.48437(18) 0.44594(17) 0.28810(11) 0.0509(4) Uani 1 1 d . . . . .
H16 H 0.403316 0.473835 0.293200 0.061 Uiso 1 1 calc R U . . .
C21 C 0.64426(15) 0.76078(15) 0.32100(9) 0.0426(3) Uani 1 1 d . . . . .
C22 C 0.77911(18) 0.84722(18) 0.34076(11) 0.0579(4) Uani 1 1 d . . . . .
H22 H 0.844379 0.846464 0.301184 0.070 Uiso 1 1 calc R U . . .
C23 C 0.8195(2) 0.93545(19) 0.41865(13) 0.0690(5) Uani 1 1 d . . . . .
H23 H 0.910411 0.994277 0.430618 0.083 Uiso 1 1 calc R U . . .
C24 C 0.7250(2) 0.93531(18) 0.47743(11) 0.0606(5) Uani 1 1 d . . . . .
C25 C 0.5904(2) 0.8506(2) 0.46036(11) 0.0645(5) Uani 1 1 d . . . . .
H25 H 0.526130 0.851520 0.500546 0.077 Uiso 1 1 calc R U . . .
C26 C 0.55130(18) 0.76331(18) 0.38230(10) 0.0582(4) Uani 1 1 d . . . . .
H26 H 0.460107 0.704865 0.370813 0.070 Uiso 1 1 calc R U . . .
C31 C 0.52752(16) 0.84277(14) 0.09265(9) 0.0417(3) Uani 1 1 d . . . . .
C32 C 0.47894(17) 0.75287(14) 0.01490(9) 0.0441(4) Uani 1 1 d . . . . .
C33 C 0.5463(2) 0.77284(17) -0.05913(11) 0.0580(5) Uani 1 1 d . . . . .
H33 H 0.514886 0.712599 -0.110679 0.070 Uiso 1 1 calc R U . . .
C34 C 0.6601(2) 0.8824(2) -0.05602(14) 0.0716(6) Uani 1 1 d . . . . .
H34 H 0.705318 0.896321 -0.105825 0.086 Uiso 1 1 calc R U . . .
C35 C 0.7077(2) 0.97177(19) 0.02033(14) 0.0684(5) Uani 1 1 d . . . . .
H35 H 0.784956 1.045358 0.021664 0.082 Uiso 1 1 calc R U . . .
C36 C 0.64128(18) 0.95278(15) 0.09517(12) 0.0535(4) Uani 1 1 d . . . . .
H36 H 0.673091 1.013537 0.146450 0.064 Uiso 1 1 calc R U . . .
C41 C 0.28831(16) 0.78397(13) 0.13406(9) 0.0406(3) Uani 1 1 d . . . . .
C42 C 0.24009(17) 0.69437(14) 0.05617(9) 0.0445(4) Uani 1 1 d . . . . .
C43 C 0.09871(19) 0.66471(17) 0.01809(12) 0.0591(5) Uani 1 1 d . . . . .
H43 H 0.065956 0.605239 -0.033742 0.071 Uiso 1 1 calc R U . . .
C44 C 0.0067(2) 0.7232(2) 0.05689(15) 0.0723(6) Uani 1 1 d . . . . .
H44 H -0.088021 0.702809 0.031140 0.087 Uiso 1 1 calc R U . . .
C45 C 0.0542(2) 0.8116(2) 0.13364(15) 0.0682(5) Uani 1 1 d . . . . .
H45 H -0.008331 0.851112 0.159277 0.082 Uiso 1 1 calc R U . . .
C46 C 0.19537(18) 0.84180(16) 0.17276(11) 0.0524(4) Uani 1 1 d . . . . .
H46 H 0.227171 0.900814 0.224859 0.063 Uiso 1 1 calc R U . . .
C51 C 0.0882(7) 0.2828(2) 0.2842(3) 0.0546(12) Uani 0.581(8) 1 d DG . P A 1
C52 C 0.1265(8) 0.3338(6) 0.3734(3) 0.0724(18) Uani 0.581(8) 1 d DG . P A 1
H52 H 0.134013 0.278051 0.415225 0.087 Uiso 0.581(8) 1 calc R U P A 1
C53 C 0.1534(6) 0.4680(6) 0.4002(2) 0.0819(17) Uani 0.581(8) 1 d DG . P A 1
C54 C 0.1422(5) 0.5513(3) 0.3378(5) 0.081(2) Uani 0.581(8) 1 d DG . P A 1
H54 H 0.160194 0.641075 0.355676 0.097 Uiso 0.581(8) 1 calc R U P A 1
C55 C 0.1039(5) 0.5003(4) 0.2485(4) 0.0702(17) Uani 0.581(8) 1 d DG . P A 1
H55 H 0.096393 0.555967 0.206701 0.084 Uiso 0.581(8) 1 calc R U P A 1
C56 C 0.0770(4) 0.3660(4) 0.22170(18) 0.0611(11) Uani 0.581(8) 1 d DG . P A 1
H56 H 0.051402 0.331900 0.161986 0.073 Uiso 0.581(8) 1 calc R U P A 1
C57 C 0.0569(7) 0.1371(4) 0.2526(5) 0.1060(19) Uani 0.581(8) 1 d D . P A 1
H57A H -0.036809 0.092014 0.263748 0.159 Uiso 0.581(8) 1 calc R U P A 1
H57B H 0.126102 0.103296 0.283886 0.159 Uiso 0.581(8) 1 calc R U P A 1
H57C H 0.061585 0.123479 0.190281 0.159 Uiso 0.581(8) 1 calc R U P A 1
C58 C 0.2044(9) 0.5238(12) 0.4954(4) 0.174(5) Uani 0.581(8) 1 d D . P A 1
H58A H 0.305499 0.537176 0.507613 0.262 Uiso 0.581(8) 1 calc R U P A 1
H58B H 0.156879 0.463568 0.532253 0.262 Uiso 0.581(8) 1 calc R U P A 1
H58C H 0.183485 0.606342 0.507623 0.262 Uiso 0.581(8) 1 calc R U P A 1
C61 C 0.0899(9) 0.3260(9) 0.2651(4) 0.079(2) Uani 0.419(8) 1 d DG . P A 2
C62 C 0.1228(12) 0.3143(5) 0.3537(5) 0.066(2) Uani 0.419(8) 1 d DG . P A 2
H62 H 0.124191 0.233027 0.369957 0.079 Uiso 0.419(8) 1 calc R U P A 2
C63 C 0.1535(10) 0.4241(7) 0.4181(3) 0.082(2) Uani 0.419(8) 1 d DG . P A 2
C64 C 0.1513(6) 0.5456(5) 0.3938(6) 0.085(2) Uani 0.419(8) 1 d DG . P A 2
H64 H 0.171898 0.619054 0.436851 0.102 Uiso 0.419(8) 1 calc R U P A 2
C65 C 0.1185(8) 0.5573(8) 0.3052(7) 0.089(3) Uani 0.419(8) 1 d DG . P A 2
H65 H 0.117025 0.638537 0.288995 0.107 Uiso 0.419(8) 1 calc R U P A 2
C66 C 0.0877(8) 0.4475(12) 0.2409(4) 0.091(3) Uani 0.419(8) 1 d DG . P A 2
H66 H 0.065734 0.455265 0.181619 0.109 Uiso 0.419(8) 1 calc R U P A 2
C67 C 0.0538(11) 0.2056(14) 0.2018(8) 0.169(6) Uani 0.419(8) 1 d D . P A 2
H67A H -0.027313 0.142839 0.216863 0.254 Uiso 0.419(8) 1 calc R U P A 2
H67B H 0.133437 0.169582 0.203650 0.254 Uiso 0.419(8) 1 calc R U P A 2
H67C H 0.031359 0.225290 0.143328 0.254 Uiso 0.419(8) 1 calc R U P A 2
C68 C 0.1859(15) 0.4189(13) 0.5174(5) 0.143(4) Uani 0.419(8) 1 d D . P A 2
H68A H 0.126356 0.460116 0.548986 0.214 Uiso 0.419(8) 1 calc R U P A 2
H68B H 0.284284 0.464589 0.538068 0.214 Uiso 0.419(8) 1 calc R U P A 2
H68C H 0.167167 0.328858 0.527403 0.214 Uiso 0.419(8) 1 calc R U P A 2


_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 1.7417(17) . ?
Cl2 C24 1.7450(16) . ?
O1 C1 1.4276(18) . ?
O1 H1 0.8200 . ?
C1 C11 1.532(2) . ?
C1 C21 1.5411(19) . ?
C1 C2 1.555(2) . ?
C2 C4 1.5545(17) . ?
C2 C3 1.566(2) . ?
C2 H2 0.9800 . ?
C3 C41 1.510(2) . ?
C3 C31 1.518(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.557(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C32 1.504(2) . ?
C5 C42 1.509(2) . ?
C5 H5 0.9800 . ?
C11 C16 1.381(2) . ?
C11 C12 1.391(2) . ?
C12 C13 1.379(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C22 1.377(2) . ?
C21 C26 1.382(2) . ?
C22 C23 1.388(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.362(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.366(3) . ?
C25 C26 1.384(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C31 C36 1.379(2) . ?
C31 C32 1.3982(19) . ?
C32 C33 1.382(2) . ?
C33 C34 1.375(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.379(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.387(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C41 C46 1.381(2) . ?
C41 C42 1.3981(19) . ?
C42 C43 1.387(2) . ?
C43 C44 1.378(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.378(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.389(3) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C51 C52 1.3900 . ?
C51 C56 1.3900 . ?
C51 C57 1.513(5) . ?
C52 C53 1.3900 . ?
C52 H52 0.9300 . ?
C53 C54 1.3900 . ?
C53 C58 1.495(5) . ?
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 1.458(8) . ?
C62 C63 1.3900 . ?
C62 H62 0.9300 . ?
C63 C64 1.3900 . ?
C63 C68 1.534(7) . ?
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_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 105.92(11) . . ?
O1 C1 C21 109.78(12) . . ?
C11 C1 C21 107.94(11) . . ?
O1 C1 C2 110.75(11) . . ?
C11 C1 C2 111.64(11) . . ?
C21 C1 C2 110.67(11) . . ?
C4 C2 C1 112.00(11) . . ?
C4 C2 C3 108.43(10) . . ?
C1 C2 C3 114.72(11) . . ?
C4 C2 H2 107.1 . . ?
C1 C2 H2 107.1 . . ?
C3 C2 H2 107.1 . . ?
C41 C3 C31 107.16(11) . . ?
C41 C3 C2 105.11(11) . . ?
C31 C3 C2 108.95(11) . . ?
C41 C3 H3 111.8 . . ?
C31 C3 H3 111.8 . . ?
C2 C3 H3 111.8 . . ?
C2 C4 C5 109.75(11) . . ?
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 . . ?
C32 C5 C42 107.66(12) . . ?
C32 C5 C4 106.54(12) . . ?
C42 C5 C4 107.12(12) . . ?
C32 C5 H5 111.7 . . ?
C42 C5 H5 111.7 . . ?
C4 C5 H5 111.7 . . ?
C16 C11 C12 117.53(15) . . ?
C16 C11 C1 122.75(13) . . ?
C12 C11 C1 119.70(13) . . ?
C13 C12 C11 121.40(16) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 119.63(15) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.69(15) . . ?
C13 C14 Cl1 119.69(13) . . ?
C15 C14 Cl1 119.62(14) . . ?
C14 C15 C16 119.11(16) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 121.63(15) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C22 C21 C26 117.61(14) . . ?
C22 C21 C1 120.66(14) . . ?
C26 C21 C1 121.72(13) . . ?
C21 C22 C23 121.21(16) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 119.55(16) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 120.93(15) . . ?
C23 C24 Cl2 119.65(14) . . ?
C25 C24 Cl2 119.39(15) . . ?
C24 C25 C26 118.98(16) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C21 C26 C25 121.71(16) . . ?
C21 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C36 C31 C32 120.05(14) . . ?
C36 C31 C3 126.98(13) . . ?
C32 C31 C3 112.97(12) . . ?
C33 C32 C31 120.10(15) . . ?
C33 C32 C5 126.85(13) . . ?
C31 C32 C5 113.03(12) . . ?
C34 C33 C32 119.53(16) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C35 120.55(16) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C34 C35 C36 120.51(17) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C35 119.24(16) . . ?
C31 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C46 C41 C42 120.05(14) . . ?
C46 C41 C3 127.00(13) . . ?
C42 C41 C3 112.93(12) . . ?
C43 C42 C41 119.49(15) . . ?
C43 C42 C5 127.39(14) . . ?
C41 C42 C5 113.11(13) . . ?
C44 C43 C42 120.15(17) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C45 120.40(17) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
C44 C45 C46 120.09(17) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C41 C46 C45 119.82(16) . . ?
C41 C46 H46 120.1 . . ?
C45 C46 H46 120.1 . . ?
C52 C51 C56 120.0 . . ?
C52 C51 C57 121.5(4) . . ?
C56 C51 C57 118.5(4) . . ?
C53 C52 C51 120.0 . . ?
C53 C52 H52 120.0 . . ?
C51 C52 H52 120.0 . . ?
C52 C53 C54 120.0 . . ?
C52 C53 C58 119.8(6) . . ?
C54 C53 C58 120.0(6) . . ?
C55 C54 C53 120.0 . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C56 C55 C54 120.0 . . ?
C56 C55 H55 120.0 . . ?
C54 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 . . ?
C53 C58 H58A 109.5 . . ?
C53 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C53 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C62 C61 C66 120.0 . . ?
C62 C61 C67 116.9(8) . . ?
C66 C61 C67 123.1(8) . . ?
C63 C62 C61 120.0 . . ?
C63 C62 H62 120.0 . . ?
C61 C62 H62 120.0 . . ?
C62 C63 C64 120.0 . . ?
C62 C63 C68 123.3(6) . . ?
C64 C63 C68 116.6(6) . . ?
C63 C64 C65 120.0 . . ?
C63 C64 H64 120.0 . . ?
C65 C64 H64 120.0 . . ?
C66 C65 C64 120.0 . . ?
C66 C65 H65 120.0 . . ?
C64 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 . . ?
C63 C68 H68A 109.5 . . ?
C63 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
C63 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?

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 57.48(15) . . . . ?
C11 C1 C2 C4 -60.28(15) . . . . ?
C21 C1 C2 C4 179.46(11) . . . . ?
O1 C1 C2 C3 -66.67(14) . . . . ?
C11 C1 C2 C3 175.57(10) . . . . ?
C21 C1 C2 C3 55.31(15) . . . . ?
C4 C2 C3 C41 61.58(14) . . . . ?
C1 C2 C3 C41 -172.40(11) . . . . ?
C4 C2 C3 C31 -53.00(14) . . . . ?
C1 C2 C3 C31 73.03(14) . . . . ?
C1 C2 C4 C5 -132.52(13) . . . . ?
C3 C2 C4 C5 -4.92(16) . . . . ?
C2 C4 C5 C32 60.88(15) . . . . ?
C2 C4 C5 C42 -54.12(15) . . . . ?
O1 C1 C11 C16 -160.39(13) . . . . ?
C21 C1 C11 C16 82.08(16) . . . . ?
C2 C1 C11 C16 -39.76(18) . . . . ?
O1 C1 C11 C12 21.52(17) . . . . ?
C21 C1 C11 C12 -96.01(15) . . . . ?
C2 C1 C11 C12 142.15(13) . . . . ?
C16 C11 C12 C13 -1.0(2) . . . . ?
C1 C11 C12 C13 177.22(14) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C12 C13 C14 Cl1 -179.37(13) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
Cl1 C14 C15 C16 179.10(12) . . . . ?
C12 C11 C16 C15 0.7(2) . . . . ?
C1 C11 C16 C15 -177.44(14) . . . . ?
C14 C15 C16 C11 -0.1(2) . . . . ?
O1 C1 C21 C22 -10.1(2) . . . . ?
C11 C1 C21 C22 104.90(16) . . . . ?
C2 C1 C21 C22 -132.65(15) . . . . ?
O1 C1 C21 C26 171.21(14) . . . . ?
C11 C1 C21 C26 -73.78(18) . . . . ?
C2 C1 C21 C26 48.7(2) . . . . ?
C26 C21 C22 C23 -1.2(3) . . . . ?
C1 C21 C22 C23 -179.93(16) . . . . ?
C21 C22 C23 C24 1.1(3) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C22 C23 C24 Cl2 -178.87(15) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
Cl2 C24 C25 C26 178.67(15) . . . . ?
C22 C21 C26 C25 1.0(3) . . . . ?
C1 C21 C26 C25 179.72(16) . . . . ?
C24 C25 C26 C21 -0.7(3) . . . . ?
C41 C3 C31 C36 125.56(16) . . . . ?
C2 C3 C31 C36 -121.21(16) . . . . ?
C41 C3 C31 C32 -54.86(16) . . . . ?
C2 C3 C31 C32 58.37(16) . . . . ?
C36 C31 C32 C33 1.1(2) . . . . ?
C3 C31 C32 C33 -178.51(14) . . . . ?
C36 C31 C32 C5 179.88(14) . . . . ?
C3 C31 C32 C5 0.27(18) . . . . ?
C42 C5 C32 C33 -126.86(17) . . . . ?
C4 C5 C32 C33 118.51(17) . . . . ?
C42 C5 C32 C31 54.46(16) . . . . ?
C4 C5 C32 C31 -60.17(16) . . . . ?
C31 C32 C33 C34 -0.8(3) . . . . ?
C5 C32 C33 C34 -179.37(17) . . . . ?
C32 C33 C34 C35 0.3(3) . . . . ?
C33 C34 C35 C36 -0.2(3) . . . . ?
C32 C31 C36 C35 -1.0(2) . . . . ?
C3 C31 C36 C35 178.60(16) . . . . ?
C34 C35 C36 C31 0.5(3) . . . . ?
C31 C3 C41 C46 -126.72(15) . . . . ?
C2 C3 C41 C46 117.47(15) . . . . ?
C31 C3 C41 C42 54.70(15) . . . . ?
C2 C3 C41 C42 -61.11(14) . . . . ?
C46 C41 C42 C43 0.3(2) . . . . ?
C3 C41 C42 C43 178.96(14) . . . . ?
C46 C41 C42 C5 -178.97(13) . . . . ?
C3 C41 C42 C5 -0.28(18) . . . . ?
C32 C5 C42 C43 126.18(16) . . . . ?
C4 C5 C42 C43 -119.57(17) . . . . ?
C32 C5 C42 C41 -54.65(16) . . . . ?
C4 C5 C42 C41 59.60(16) . . . . ?
C41 C42 C43 C44 0.0(2) . . . . ?
C5 C42 C43 C44 179.09(16) . . . . ?
C42 C43 C44 C45 0.1(3) . . . . ?
C43 C44 C45 C46 -0.4(3) . . . . ?
C42 C41 C46 C45 -0.6(2) . . . . ?
C3 C41 C46 C45 -179.06(16) . . . . ?
C44 C45 C46 C41 0.6(3) . . . . ?
C56 C51 C52 C53 0.0 . . . . ?
C57 C51 C52 C53 -179.5(6) . . . . ?
C51 C52 C53 C54 0.0 . . . . ?
C51 C52 C53 C58 -175.7(6) . . . . ?
C52 C53 C54 C55 0.0 . . . . ?
C58 C53 C54 C55 175.7(6) . . . . ?
C53 C54 C55 C56 0.0 . . . . ?
C54 C55 C56 C51 0.0 . . . . ?
C52 C51 C56 C55 0.0 . . . . ?
C57 C51 C56 C55 179.5(6) . . . . ?
C66 C61 C62 C63 0.0 . . . . ?
C67 C61 C62 C63 -177.8(8) . . . . ?
C61 C62 C63 C64 0.0 . . . . ?
C61 C62 C63 C68 177.9(10) . . . . ?
C62 C63 C64 C65 0.0 . . . . ?
C68 C63 C64 C65 -178.0(9) . . . . ?
C63 C64 C65 C66 0.0 . . . . ?
C64 C65 C66 C61 0.0 . . . . ?
C62 C61 C66 C65 0.0 . . . . ?
C67 C61 C66 C65 177.7(8) . . . . ?

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 2.55 2.963(2) 106 . yes
C12 H12 O1 0.93 2.30 2.661(2) 102 . yes
C22 H22 O1 0.93 2.37 2.740(2) 103 . yes

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_ka111
_database_code_depnum_ccdc_archive 'CCDC 2089001'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-06-09 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
α,α-Bis(p-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11-methanol
;
_chemical_name_common            ?
_chemical_melting_point          397.15
_chemical_formula_moiety         'C29 H22 Cl2 O, C8 H10'
_chemical_formula_sum            'C37 H32 Cl2 O'
_chemical_formula_weight         563.52

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.8151(4)
_cell_length_b                   10.9036(5)
_cell_length_c                   14.5415(6)
_cell_angle_alpha                94.486(2)
_cell_angle_beta                 97.7538(19)
_cell_angle_gamma                104.6528(19)
_cell_volume                     1481.57(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9795
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.182
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_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            53899
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.944
_diffrn_reflns_theta_max         28.335
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7364
_reflns_number_gt                5923
_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       '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          
;
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 methyl groups were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(C).

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+0.6015P] 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         7364
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.65141(6) 0.15797(4) 0.34510(3) 0.05640(14) Uani 1 1 d . . . . .
Cl2 Cl 0.78215(7) 1.06492(5) 0.58412(3) 0.07093(17) Uani 1 1 d . . . . .
O1 O 0.71400(10) 0.70771(10) 0.17875(7) 0.0331(2) Uani 1 1 d . . . . .
H1 H 0.697359 0.766346 0.148554 0.050 Uiso 1 1 calc R U . . .
C1 C 0.61167(13) 0.67562(13) 0.24011(9) 0.0269(3) Uani 1 1 d . . . . .
C2 C 0.45957(13) 0.66851(12) 0.18958(9) 0.0252(2) Uani 1 1 d . . . . .
H2 H 0.391328 0.635597 0.232812 0.030 Uiso 1 1 calc R U . . .
C3 C 0.41677(14) 0.57340(12) 0.09876(9) 0.0291(3) Uani 1 1 d . . . . .
H3A H 0.342490 0.496960 0.107912 0.035 Uiso 1 1 calc R U . . .
H3B H 0.500823 0.545653 0.084220 0.035 Uiso 1 1 calc R U . . .
C4 C 0.35889(14) 0.63822(12) 0.01603(9) 0.0288(3) Uani 1 1 d . . . . .
H4 H 0.327163 0.578342 -0.043117 0.035 Uiso 1 1 calc R U . . .
C5 C 0.43794(13) 0.80076(12) 0.16545(9) 0.0256(2) Uani 1 1 d . . . . .
H5 H 0.466907 0.866462 0.221431 0.031 Uiso 1 1 calc R U . . .
C11 C 0.62083(13) 0.54512(13) 0.26828(9) 0.0282(3) Uani 1 1 d . . . . .
C12 C 0.51635(15) 0.46938(15) 0.31044(11) 0.0371(3) Uani 1 1 d . . . . .
H12 H 0.437103 0.499461 0.322805 0.045 Uiso 1 1 calc R U . . .
C13 C 0.52506(17) 0.35089(15) 0.33488(11) 0.0395(3) Uani 1 1 d . . . . .
H13 H 0.452195 0.299884 0.363080 0.047 Uiso 1 1 calc R U . . .
C14 C 0.64082(17) 0.30818(14) 0.31771(10) 0.0363(3) Uani 1 1 d . . . . .
C15 C 0.74808(17) 0.38246(16) 0.27863(12) 0.0420(4) Uani 1 1 d . . . . .
H15 H 0.828815 0.353227 0.268607 0.050 Uiso 1 1 calc R U . . .
C16 C 0.73751(15) 0.50036(15) 0.25397(11) 0.0360(3) Uani 1 1 d . . . . .
H16 H 0.811552 0.551456 0.226749 0.043 Uiso 1 1 calc R U . . .
C21 C 0.65355(14) 0.77324(13) 0.32786(9) 0.0291(3) Uani 1 1 d . . . . .
C22 C 0.56045(16) 0.77803(16) 0.39192(10) 0.0385(3) Uani 1 1 d . . . . .
H22 H 0.468479 0.719379 0.381181 0.046 Uiso 1 1 calc R U . . .
C23 C 0.59969(19) 0.86657(17) 0.47067(11) 0.0440(4) Uani 1 1 d . . . . .
H23 H 0.535371 0.868710 0.513704 0.053 Uiso 1 1 calc R U . . .
C24 C 0.73269(19) 0.95144(16) 0.48604(11) 0.0436(4) Uani 1 1 d . . . . .
C25 C 0.82685(18) 0.94980(17) 0.42446(12) 0.0460(4) Uani 1 1 d . . . . .
H25 H 0.918138 1.009543 0.435410 0.055 Uiso 1 1 calc R U . . .
C26 C 0.78715(15) 0.85994(15) 0.34614(11) 0.0379(3) Uani 1 1 d . . . . .
H26 H 0.852858 0.857694 0.304084 0.046 Uiso 1 1 calc R U . . .
C31 C 0.51983(13) 0.84187(12) 0.08698(9) 0.0258(3) Uani 1 1 d . . . . .
C32 C 0.47793(14) 0.75340(12) 0.00653(9) 0.0276(3) Uani 1 1 d . . . . .
C33 C 0.54682(16) 0.77517(14) -0.07000(10) 0.0348(3) Uani 1 1 d . . . . .
H33 H 0.519205 0.715318 -0.124663 0.042 Uiso 1 1 calc R U . . .
C34 C 0.65662(18) 0.88529(15) -0.06608(11) 0.0411(4) Uani 1 1 d . . . . .
H34 H 0.704138 0.900528 -0.118487 0.049 Uiso 1 1 calc R U . . .
C35 C 0.69792(16) 0.97329(14) 0.01315(11) 0.0382(3) Uani 1 1 d . . . . .
H35 H 0.773121 1.048390 0.014744 0.046 Uiso 1 1 calc R U . . .
C36 C 0.62929(14) 0.95184(13) 0.09057(10) 0.0313(3) Uani 1 1 d . . . . .
H36 H 0.657238 1.011892 0.145119 0.038 Uiso 1 1 calc R U . . .
C41 C 0.28119(14) 0.77408(12) 0.12661(9) 0.0276(3) Uani 1 1 d . . . . .
C42 C 0.23851(14) 0.68697(13) 0.04574(10) 0.0300(3) Uani 1 1 d . . . . .
C43 C 0.09788(16) 0.65344(15) 0.00176(12) 0.0408(3) Uani 1 1 d . . . . .
H43 H 0.068811 0.595049 -0.053686 0.049 Uiso 1 1 calc R U . . .
C44 C -0.00025(16) 0.70597(17) 0.03944(14) 0.0508(4) Uani 1 1 d . . . . .
H44 H -0.096963 0.682926 0.009742 0.061 Uiso 1 1 calc R U . . .
C45 C 0.04142(17) 0.79104(17) 0.11938(14) 0.0481(4) Uani 1 1 d . . . . .
H45 H -0.026827 0.826107 0.144521 0.058 Uiso 1 1 calc R U . . .
C46 C 0.18290(16) 0.82631(15) 0.16388(11) 0.0360(3) Uani 1 1 d . . . . .
H46 H 0.211515 0.885345 0.218987 0.043 Uiso 1 1 calc R U . . .
C51 C 0.14188(18) 0.3510(2) 0.30535(15) 0.0569(5) Uani 1 1 d . . . . .
C52 C 0.1618(2) 0.3468(2) 0.40027(16) 0.0635(5) Uani 1 1 d . . . . .
H52 H 0.169498 0.269470 0.423677 0.076 Uiso 1 1 calc R U . . .
C53 C 0.1708(3) 0.4511(3) 0.46205(16) 0.0745(6) Uani 1 1 d . . . . .
H53 H 0.185882 0.445677 0.527359 0.089 Uiso 1 1 calc R U . . .
C54 C 0.1584(3) 0.5619(2) 0.43030(17) 0.0716(6) Uani 1 1 d . . . . .
H54 H 0.163756 0.633614 0.473500 0.086 Uiso 1 1 calc R U . . .
C55 C 0.1385(2) 0.5711(2) 0.33768(17) 0.0623(5) Uani 1 1 d . . . . .
H55 H 0.130231 0.649233 0.315883 0.075 Uiso 1 1 calc R U . . .
C56 C 0.13015(18) 0.4669(2) 0.27460(14) 0.0624(6) Uani 1 1 d . . . . .
H56 H 0.116269 0.474013 0.209509 0.075 Uiso 1 1 calc R U . . .
C57 C 0.1366(3) 0.2380(3) 0.2374(3) 0.1114(12) Uani 1 1 d . . . . .
H57A H 0.168348 0.269829 0.179823 0.134 Uiso 1 1 calc R U . . .
H57B H 0.206063 0.193722 0.264817 0.134 Uiso 1 1 calc R U . . .
C58 C -0.0006(3) 0.1454(3) 0.2114(2) 0.0945(9) Uani 1 1 d . . . . .
H58A H 0.008249 0.075148 0.168266 0.142 Uiso 1 1 calc R U . . .
H58B H -0.069741 0.186326 0.180764 0.142 Uiso 1 1 calc R U . . .
H58C H -0.033445 0.111877 0.267478 0.142 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 1.7404(15) . ?
Cl2 C24 1.7419(16) . ?
O1 C1 1.4284(14) . ?
O1 H1 0.8400 . ?
C1 C11 1.5318(19) . ?
C1 C21 1.5346(19) . ?
C1 C2 1.5528(17) . ?
C2 C3 1.5529(18) . ?
C2 C5 1.5689(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.5560(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C42 1.5116(18) . ?
C4 C32 1.5132(18) . ?
C4 H4 1.0000 . ?
C5 C41 1.5114(18) . ?
C5 C31 1.5146(17) . ?
C5 H5 1.0000 . ?
C11 C16 1.3872(18) . ?
C11 C12 1.3892(19) . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.387(2) . ?
C21 C22 1.3970(19) . ?
C22 C23 1.383(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(2) . ?
C25 C26 1.386(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.3850(19) . ?
C31 C32 1.4005(18) . ?
C32 C33 1.3838(18) . ?
C33 C34 1.387(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.393(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.3855(18) . ?
C41 C42 1.3969(19) . ?
C42 C43 1.385(2) . ?
C43 C44 1.389(2) . ?
C43 H43 0.9500 . ?
C44 C45 1.375(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.394(2) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.374(3) . ?
C51 C56 1.399(3) . ?
C51 C57 1.504(3) . ?
C52 C53 1.369(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.355(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.350(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.382(3) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C57 C58 1.446(4) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?

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 105.23(10) . . ?
O1 C1 C21 109.85(11) . . ?
C11 C1 C21 108.90(10) . . ?
O1 C1 C2 110.71(10) . . ?
C11 C1 C2 110.89(10) . . ?
C21 C1 C2 111.08(10) . . ?
C1 C2 C3 111.99(10) . . ?
C1 C2 C5 114.04(10) . . ?
C3 C2 C5 108.74(10) . . ?
C1 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
C5 C2 H2 107.2 . . ?
C2 C3 C4 110.00(10) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C42 C4 C32 107.33(10) . . ?
C42 C4 C3 106.87(11) . . ?
C32 C4 C3 106.44(11) . . ?
C42 C4 H4 112.0 . . ?
C32 C4 H4 112.0 . . ?
C3 C4 H4 112.0 . . ?
C41 C5 C31 107.04(10) . . ?
C41 C5 C2 105.10(10) . . ?
C31 C5 C2 108.48(10) . . ?
C41 C5 H5 112.0 . . ?
C31 C5 H5 112.0 . . ?
C2 C5 H5 112.0 . . ?
C16 C11 C12 117.84(13) . . ?
C16 C11 C1 120.15(12) . . ?
C12 C11 C1 122.00(11) . . ?
C13 C12 C11 121.52(13) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C14 C13 C12 119.07(14) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 120.82(14) . . ?
C15 C14 Cl1 119.42(11) . . ?
C13 C14 Cl1 119.76(12) . . ?
C14 C15 C16 119.48(13) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C11 121.23(14) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C26 C21 C22 117.75(13) . . ?
C26 C21 C1 120.37(12) . . ?
C22 C21 C1 121.88(12) . . ?
C23 C22 C21 121.21(15) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 119.32(15) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C25 C24 C23 121.09(15) . . ?
C25 C24 Cl2 119.23(14) . . ?
C23 C24 Cl2 119.67(13) . . ?
C24 C25 C26 119.22(15) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C25 C26 C21 121.40(14) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
C36 C31 C32 120.57(12) . . ?
C36 C31 C5 126.26(12) . . ?
C32 C31 C5 113.13(11) . . ?
C33 C32 C31 119.94(12) . . ?
C33 C32 C4 126.89(12) . . ?
C31 C32 C4 113.15(11) . . ?
C32 C33 C34 119.33(13) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C35 C34 C33 120.92(13) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C34 C35 C36 120.07(13) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C31 C36 C35 119.17(13) . . ?
C31 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C46 C41 C42 120.26(13) . . ?
C46 C41 C5 126.30(13) . . ?
C42 C41 C5 113.44(11) . . ?
C43 C42 C41 120.13(13) . . ?
C43 C42 C4 126.80(13) . . ?
C41 C42 C4 113.07(11) . . ?
C42 C43 C44 119.39(15) . . ?
C42 C43 H43 120.3 . . ?
C44 C43 H43 120.3 . . ?
C45 C44 C43 120.54(15) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C44 C45 C46 120.61(14) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C41 C46 C45 119.07(15) . . ?
C41 C46 H46 120.5 . . ?
C45 C46 H46 120.5 . . ?
C52 C51 C56 116.80(19) . . ?
C52 C51 C57 121.9(3) . . ?
C56 C51 C57 121.3(2) . . ?
C53 C52 C51 121.7(2) . . ?
C53 C52 H52 119.1 . . ?
C51 C52 H52 119.1 . . ?
C54 C53 C52 120.2(2) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C55 C54 C53 120.5(2) . . ?
C55 C54 H54 119.8 . . ?
C53 C54 H54 119.8 . . ?
C54 C55 C56 120.0(2) . . ?
C54 C55 H55 120.0 . . ?
C56 C55 H55 120.0 . . ?
C55 C56 C51 120.85(19) . . ?
C55 C56 H56 119.6 . . ?
C51 C56 H56 119.6 . . ?
C58 C57 C51 116.2(2) . . ?
C58 C57 H57A 108.2 . . ?
C51 C57 H57A 108.2 . . ?
C58 C57 H57B 108.2 . . ?
C51 C57 H57B 108.2 . . ?
H57A C57 H57B 107.4 . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?

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 55.84(14) . . . . ?
C11 C1 C2 C3 -60.58(13) . . . . ?
C21 C1 C2 C3 178.17(10) . . . . ?
O1 C1 C2 C5 -68.17(13) . . . . ?
C11 C1 C2 C5 175.41(10) . . . . ?
C21 C1 C2 C5 54.16(13) . . . . ?
C1 C2 C3 C4 -130.19(11) . . . . ?
C5 C2 C3 C4 -3.26(14) . . . . ?
C2 C3 C4 C42 -55.09(13) . . . . ?
C2 C3 C4 C32 59.36(13) . . . . ?
C1 C2 C5 C41 -174.28(10) . . . . ?
C3 C2 C5 C41 59.98(12) . . . . ?
C1 C2 C5 C31 71.51(13) . . . . ?
C3 C2 C5 C31 -54.23(13) . . . . ?
O1 C1 C11 C16 16.28(17) . . . . ?
C21 C1 C11 C16 -101.44(14) . . . . ?
C2 C1 C11 C16 136.04(13) . . . . ?
O1 C1 C11 C12 -165.24(13) . . . . ?
C21 C1 C11 C12 77.04(16) . . . . ?
C2 C1 C11 C12 -45.49(17) . . . . ?
C16 C11 C12 C13 -2.1(2) . . . . ?
C1 C11 C12 C13 179.41(14) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C12 C13 C14 C15 1.3(2) . . . . ?
C12 C13 C14 Cl1 -178.33(12) . . . . ?
C13 C14 C15 C16 -1.7(2) . . . . ?
Cl1 C14 C15 C16 177.90(12) . . . . ?
C14 C15 C16 C11 0.2(2) . . . . ?
C12 C11 C16 C15 1.6(2) . . . . ?
C1 C11 C16 C15 -179.83(14) . . . . ?
O1 C1 C21 C26 -11.55(17) . . . . ?
C11 C1 C21 C26 103.21(14) . . . . ?
C2 C1 C21 C26 -134.37(13) . . . . ?
O1 C1 C21 C22 168.77(12) . . . . ?
C11 C1 C21 C22 -76.47(15) . . . . ?
C2 C1 C21 C22 45.95(17) . . . . ?
C26 C21 C22 C23 0.3(2) . . . . ?
C1 C21 C22 C23 -179.98(13) . . . . ?
C21 C22 C23 C24 0.1(2) . . . . ?
C22 C23 C24 C25 0.1(2) . . . . ?
C22 C23 C24 Cl2 179.04(12) . . . . ?
C23 C24 C25 C26 -0.7(3) . . . . ?
Cl2 C24 C25 C26 -179.64(12) . . . . ?
C24 C25 C26 C21 1.1(2) . . . . ?
C22 C21 C26 C25 -0.9(2) . . . . ?
C1 C21 C26 C25 179.36(14) . . . . ?
C41 C5 C31 C36 127.21(13) . . . . ?
C2 C5 C31 C36 -119.86(14) . . . . ?
C41 C5 C31 C32 -54.95(14) . . . . ?
C2 C5 C31 C32 57.98(14) . . . . ?
C36 C31 C32 C33 0.46(19) . . . . ?
C5 C31 C32 C33 -177.52(12) . . . . ?
C36 C31 C32 C4 178.91(12) . . . . ?
C5 C31 C32 C4 0.94(15) . . . . ?
C42 C4 C32 C33 -127.76(14) . . . . ?
C3 C4 C32 C33 118.10(14) . . . . ?
C42 C4 C32 C31 53.91(14) . . . . ?
C3 C4 C32 C31 -60.23(13) . . . . ?
C31 C32 C33 C34 -0.3(2) . . . . ?
C4 C32 C33 C34 -178.53(13) . . . . ?
C32 C33 C34 C35 0.0(2) . . . . ?
C33 C34 C35 C36 0.2(2) . . . . ?
C32 C31 C36 C35 -0.3(2) . . . . ?
C5 C31 C36 C35 177.40(12) . . . . ?
C34 C35 C36 C31 0.0(2) . . . . ?
C31 C5 C41 C46 -126.26(14) . . . . ?
C2 C5 C41 C46 118.52(14) . . . . ?
C31 C5 C41 C42 54.19(14) . . . . ?
C2 C5 C41 C42 -61.03(13) . . . . ?
C46 C41 C42 C43 0.7(2) . . . . ?
C5 C41 C42 C43 -179.68(12) . . . . ?
C46 C41 C42 C4 -179.02(12) . . . . ?
C5 C41 C42 C4 0.56(16) . . . . ?
C32 C4 C42 C43 125.45(15) . . . . ?
C3 C4 C42 C43 -120.70(15) . . . . ?
C32 C4 C42 C41 -54.81(14) . . . . ?
C3 C4 C42 C41 59.04(14) . . . . ?
C41 C42 C43 C44 -0.8(2) . . . . ?
C4 C42 C43 C44 178.93(14) . . . . ?
C42 C43 C44 C45 0.4(3) . . . . ?
C43 C44 C45 C46 0.2(3) . . . . ?
C42 C41 C46 C45 -0.2(2) . . . . ?
C5 C41 C46 C45 -179.75(13) . . . . ?
C44 C45 C46 C41 -0.2(2) . . . . ?
C56 C51 C52 C53 -0.5(3) . . . . ?
C57 C51 C52 C53 178.0(2) . . . . ?
C51 C52 C53 C54 0.8(4) . . . . ?
C52 C53 C54 C55 -0.7(4) . . . . ?
C53 C54 C55 C56 0.2(3) . . . . ?
C54 C55 C56 C51 0.1(3) . . . . ?
C52 C51 C56 C55 0.0(3) . . . . ?
C57 C51 C56 C55 -178.48(19) . . . . ?
C52 C51 C57 C58 85.2(4) . . . . ?
C56 C51 C57 C58 -96.4(4) . . . . ?

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
C3 H3B O1 0.99 2.52 2.9436(17) 105 . yes
C16 H16 O1 0.95 2.27 2.6351(18) 102 . yes
C26 H26 O1 0.95 2.36 2.7365(19) 103 . yes

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_ja145
_database_code_depnum_ccdc_archive 'CCDC 2088997'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
α,α-Diphenyl-9,10-dihydro-9,10-ethanoanthracene-11-methanol
;
_chemical_name_common            ?
_chemical_melting_point          464.15
_chemical_formula_moiety         'C29 H24 O, C8 H10'
_chemical_formula_sum            'C37 H34 O'
_chemical_formula_weight         494.64

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8100(6)
_cell_length_b                   30.3835(16)
_cell_length_c                   9.5691(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.685(2)
_cell_angle_gamma                90
_cell_volume                     2759.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.674
_exptl_crystal_size_mid          0.547
_exptl_crystal_size_min          0.222
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9409
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_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            83453
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         28.301
_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             6848
_reflns_number_gt                5197
_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       '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          
;
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 methyl groups were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(C).

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+1.2309P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6848
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
O1 O 0.18844(10) 0.65081(4) 0.26069(12) 0.0407(3) Uani 1 1 d . . . . .
H1 H 0.196080 0.675069 0.304107 0.061 Uiso 1 1 calc R U . . .
C1 C 0.31672(13) 0.62650(4) 0.30868(15) 0.0295(3) Uani 1 1 d . . . . .
C2 C 0.44378(14) 0.65304(4) 0.28387(14) 0.0268(3) Uani 1 1 d . . . . .
H2 H 0.528938 0.633946 0.316571 0.032 Uiso 1 1 calc R U . . .
C3 C 0.43020(14) 0.66417(5) 0.12102(14) 0.0305(3) Uani 1 1 d . . . . .
H3 H 0.404422 0.637696 0.057755 0.037 Uiso 1 1 calc R U . . .
C4 C 0.47434(16) 0.69626(5) 0.37242(15) 0.0328(3) Uani 1 1 d . . . . .
H4A H 0.559559 0.692497 0.453030 0.039 Uiso 1 1 calc R U . . .
H4B H 0.394134 0.703177 0.413984 0.039 Uiso 1 1 calc R U . . .
C5 C 0.49730(17) 0.73480(5) 0.27371(17) 0.0380(3) Uani 1 1 d . . . . .
H5 H 0.523345 0.762777 0.329066 0.046 Uiso 1 1 calc R U . . .
C11 C 0.33590(14) 0.61404(4) 0.46801(15) 0.0295(3) Uani 1 1 d . . . . .
C12 C 0.46676(15) 0.60804(5) 0.56415(16) 0.0364(3) Uani 1 1 d . . . . .
H12 H 0.549994 0.612564 0.532522 0.044 Uiso 1 1 calc R U . . .
C13 C 0.47719(18) 0.59551(6) 0.70577(17) 0.0435(4) Uani 1 1 d . . . . .
H13 H 0.567482 0.591345 0.770011 0.052 Uiso 1 1 calc R U . . .
C14 C 0.35790(19) 0.58903(5) 0.75435(18) 0.0452(4) Uani 1 1 d . . . . .
H14 H 0.365491 0.580736 0.851748 0.054 Uiso 1 1 calc R U . . .
C15 C 0.22784(18) 0.59473(6) 0.66003(18) 0.0455(4) Uani 1 1 d . . . . .
H15 H 0.145062 0.590204 0.692475 0.055 Uiso 1 1 calc R U . . .
C16 C 0.21632(16) 0.60700(5) 0.51809(17) 0.0386(3) Uani 1 1 d . . . . .
H16 H 0.125629 0.610665 0.454117 0.046 Uiso 1 1 calc R U . . .
C21 C 0.29899(15) 0.58444(5) 0.21772(15) 0.0339(3) Uani 1 1 d . . . . .
C22 C 0.40787(18) 0.55381(5) 0.24120(19) 0.0439(4) Uani 1 1 d . . . . .
H22 H 0.490713 0.558628 0.316327 0.053 Uiso 1 1 calc R U . . .
C23 C 0.3971(2) 0.51646(6) 0.1566(2) 0.0594(5) Uani 1 1 d . . . . .
H23 H 0.472889 0.496068 0.173049 0.071 Uiso 1 1 calc R U . . .
C24 C 0.2772(3) 0.50873(7) 0.0490(2) 0.0685(6) Uani 1 1 d . . . . .
H24 H 0.269770 0.482980 -0.008718 0.082 Uiso 1 1 calc R U . . .
C25 C 0.1685(3) 0.53824(8) 0.0252(2) 0.0674(6) Uani 1 1 d . . . . .
H25 H 0.085318 0.532796 -0.048894 0.081 Uiso 1 1 calc R U . . .
C26 C 0.17861(19) 0.57627(6) 0.10894(18) 0.0500(4) Uani 1 1 d . . . . .
H26 H 0.102649 0.596624 0.091242 0.060 Uiso 1 1 calc R U . . .
C31 C 0.32494(15) 0.70094(6) 0.07597(16) 0.0401(4) Uani 1 1 d . . . . .
C32 C 0.36149(17) 0.73909(5) 0.15814(18) 0.0437(4) Uani 1 1 d . . . . .
C33 C 0.2724(2) 0.77537(7) 0.1312(3) 0.0681(7) Uani 1 1 d . . . . .
H33 H 0.295739 0.801456 0.186898 0.082 Uiso 1 1 calc R U . . .
C34 C 0.1484(3) 0.77296(11) 0.0217(3) 0.0935(11) Uani 1 1 d . . . . .
H34 H 0.086668 0.797559 0.002478 0.112 Uiso 1 1 calc R U . . .
C35 C 0.1147(2) 0.73528(12) -0.0587(3) 0.0897(10) Uani 1 1 d . . . . .
H35 H 0.029713 0.734223 -0.133147 0.108 Uiso 1 1 calc R U . . .
C36 C 0.20204(18) 0.69877(8) -0.0338(2) 0.0610(6) Uani 1 1 d . . . . .
H36 H 0.178267 0.672894 -0.090456 0.073 Uiso 1 1 calc R U . . .
C41 C 0.57311(14) 0.68217(5) 0.11809(14) 0.0290(3) Uani 1 1 d . . . . .
C42 C 0.61005(15) 0.72010(5) 0.20135(15) 0.0326(3) Uani 1 1 d . . . . .
C43 C 0.73973(18) 0.73954(6) 0.21268(17) 0.0437(4) Uani 1 1 d . . . . .
H43 H 0.765251 0.765359 0.269246 0.052 Uiso 1 1 calc R U . . .
C44 C 0.83260(17) 0.72117(6) 0.14103(17) 0.0475(4) Uani 1 1 d . . . . .
H44 H 0.921612 0.734575 0.148316 0.057 Uiso 1 1 calc R U . . .
C45 C 0.79650(17) 0.68378(6) 0.05979(16) 0.0437(4) Uani 1 1 d . . . . .
H45 H 0.860877 0.671377 0.011477 0.052 Uiso 1 1 calc R U . . .
C46 C 0.66647(16) 0.66389(5) 0.04764(15) 0.0369(3) Uani 1 1 d . . . . .
H46 H 0.641857 0.637965 -0.008577 0.044 Uiso 1 1 calc R U . . .
C51 C 0.17501(17) 0.44296(6) 0.4441(2) 0.0520(4) Uani 1 1 d . . . . .
C52 C 0.17362(16) 0.41700(6) 0.56425(19) 0.0440(4) Uani 1 1 d . . . . .
C53 C 0.16243(18) 0.37197(6) 0.5496(2) 0.0558(5) Uani 1 1 d . . . . .
H53 H 0.163131 0.354543 0.632155 0.067 Uiso 1 1 calc R U . . .
C54 C 0.1506(2) 0.35195(8) 0.4218(3) 0.0739(7) Uani 1 1 d . . . . .
H54 H 0.143777 0.320797 0.415048 0.089 Uiso 1 1 calc R U . . .
C55 C 0.1482(2) 0.37665(11) 0.3010(3) 0.0847(8) Uani 1 1 d . . . . .
H55 H 0.137614 0.362785 0.209852 0.102 Uiso 1 1 calc R U . . .
C56 C 0.1615(2) 0.42203(10) 0.3133(2) 0.0719(7) Uani 1 1 d . . . . .
H56 H 0.161399 0.439059 0.230017 0.086 Uiso 1 1 calc R U . . .
C57 C 0.1939(3) 0.49183(8) 0.4576(4) 0.0987(10) Uani 1 1 d . . . . .
H57A H 0.177002 0.504926 0.361144 0.148 Uiso 1 1 calc R U . . .
H57B H 0.290265 0.498516 0.512804 0.148 Uiso 1 1 calc R U . . .
H57C H 0.126851 0.504030 0.507759 0.148 Uiso 1 1 calc R U . . .
C58 C 0.1831(2) 0.43743(9) 0.7085(2) 0.0808(7) Uani 1 1 d . . . . .
H58A H 0.269201 0.455125 0.737156 0.121 Uiso 1 1 calc R U . . .
H58B H 0.185379 0.414245 0.780264 0.121 Uiso 1 1 calc R U . . .
H58C H 0.100864 0.456327 0.702704 0.121 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
O1 C1 1.4309(16) . ?
O1 H1 0.8400 . ?
C1 C21 1.531(2) . ?
C1 C11 1.5356(19) . ?
C1 C2 1.5526(18) . ?
C2 C4 1.5501(18) . ?
C2 C3 1.5669(18) . ?
C2 H2 1.0000 . ?
C3 C31 1.508(2) . ?
C3 C41 1.5118(18) . ?
C3 H3 1.0000 . ?
C4 C5 1.556(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C32 1.506(2) . ?
C5 C42 1.5134(19) . ?
C5 H5 1.0000 . ?
C11 C12 1.389(2) . ?
C11 C16 1.3915(19) . ?
C12 C13 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.374(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.384(2) . ?
C21 C22 1.391(2) . ?
C22 C23 1.382(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.373(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.367(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.385(2) . ?
C31 C32 1.395(2) . ?
C32 C33 1.390(2) . ?
C33 C34 1.392(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.372(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.3838(19) . ?
C41 C42 1.396(2) . ?
C42 C43 1.382(2) . ?
C43 C44 1.389(2) . ?
C43 H43 0.9500 . ?
C44 C45 1.371(2) . ?
C44 H44 0.9500 . ?
C45 C46 1.389(2) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C56 1.380(3) . ?
C51 C52 1.397(2) . ?
C51 C57 1.498(3) . ?
C52 C53 1.377(3) . ?
C52 C58 1.495(3) . ?
C53 C54 1.344(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.374(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.387(4) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?

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 C21 106.53(11) . . ?
O1 C1 C11 108.80(11) . . ?
C21 C1 C11 109.05(11) . . ?
O1 C1 C2 110.95(11) . . ?
C21 C1 C2 109.06(11) . . ?
C11 C1 C2 112.26(11) . . ?
C4 C2 C1 114.08(11) . . ?
C4 C2 C3 108.47(11) . . ?
C1 C2 C3 113.26(10) . . ?
C4 C2 H2 106.9 . . ?
C1 C2 H2 106.9 . . ?
C3 C2 H2 106.9 . . ?
C31 C3 C41 107.31(12) . . ?
C31 C3 C2 108.88(11) . . ?
C41 C3 C2 104.54(10) . . ?
C31 C3 H3 111.9 . . ?
C41 C3 H3 111.9 . . ?
C2 C3 H3 111.9 . . ?
C2 C4 C5 110.08(11) . . ?
C2 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C2 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.2 . . ?
C32 C5 C42 107.62(12) . . ?
C32 C5 C4 105.88(12) . . ?
C42 C5 C4 106.90(12) . . ?
C32 C5 H5 112.0 . . ?
C42 C5 H5 112.0 . . ?
C4 C5 H5 112.0 . . ?
C12 C11 C16 118.04(13) . . ?
C12 C11 C1 123.37(12) . . ?
C16 C11 C1 118.56(12) . . ?
C13 C12 C11 120.69(13) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.69(15) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.13(15) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.61(14) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.84(15) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C26 C21 C22 118.36(15) . . ?
C26 C21 C1 121.97(14) . . ?
C22 C21 C1 119.64(13) . . ?
C23 C22 C21 120.86(17) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 119.76(18) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 120.55(18) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.22(19) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C36 C31 C32 121.11(17) . . ?
C36 C31 C3 125.63(17) . . ?
C32 C31 C3 113.25(13) . . ?
C33 C32 C31 119.65(19) . . ?
C33 C32 C5 127.05(19) . . ?
C31 C32 C5 113.26(13) . . ?
C32 C33 C34 119.1(2) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 H33 120.4 . . ?
C35 C34 C33 120.4(2) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 121.4(2) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
C35 C36 C31 118.3(2) . . ?
C35 C36 H36 120.9 . . ?
C31 C36 H36 120.9 . . ?
C46 C41 C42 120.10(13) . . ?
C46 C41 C3 126.53(13) . . ?
C42 C41 C3 113.32(12) . . ?
C43 C42 C41 119.89(13) . . ?
C43 C42 C5 127.09(13) . . ?
C41 C42 C5 113.00(12) . . ?
C42 C43 C44 119.72(14) . . ?
C42 C43 H43 120.1 . . ?
C44 C43 H43 120.1 . . ?
C45 C44 C43 120.36(14) . . ?
C45 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C44 C45 C46 120.48(14) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C41 C46 C45 119.45(14) . . ?
C41 C46 H46 120.3 . . ?
C45 C46 H46 120.3 . . ?
C56 C51 C52 117.88(19) . . ?
C56 C51 C57 121.1(2) . . ?
C52 C51 C57 121.0(2) . . ?
C53 C52 C51 119.61(18) . . ?
C53 C52 C58 119.45(19) . . ?
C51 C52 C58 120.94(19) . . ?
C54 C53 C52 121.9(2) . . ?
C54 C53 H53 119.0 . . ?
C52 C53 H53 119.0 . . ?
C53 C54 C55 119.8(2) . . ?
C53 C54 H54 120.1 . . ?
C55 C54 H54 120.1 . . ?
C54 C55 C56 119.3(2) . . ?
C54 C55 H55 120.3 . . ?
C56 C55 H55 120.3 . . ?
C51 C56 C55 121.4(2) . . ?
C51 C56 H56 119.3 . . ?
C55 C56 H56 119.3 . . ?
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 . . ?

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 63.88(15) . . . . ?
C21 C1 C2 C4 -179.07(11) . . . . ?
C11 C1 C2 C4 -58.10(15) . . . . ?
O1 C1 C2 C3 -60.85(14) . . . . ?
C21 C1 C2 C3 56.20(14) . . . . ?
C11 C1 C2 C3 177.17(11) . . . . ?
C4 C2 C3 C31 -52.19(14) . . . . ?
C1 C2 C3 C31 75.53(14) . . . . ?
C4 C2 C3 C41 62.24(13) . . . . ?
C1 C2 C3 C41 -170.04(11) . . . . ?
C1 C2 C4 C5 -133.38(12) . . . . ?
C3 C2 C4 C5 -6.13(15) . . . . ?
C2 C4 C5 C32 61.26(15) . . . . ?
C2 C4 C5 C42 -53.28(16) . . . . ?
O1 C1 C11 C12 -151.26(13) . . . . ?
C21 C1 C11 C12 92.91(15) . . . . ?
C2 C1 C11 C12 -28.07(18) . . . . ?
O1 C1 C11 C16 30.85(17) . . . . ?
C21 C1 C11 C16 -84.97(15) . . . . ?
C2 C1 C11 C16 154.05(12) . . . . ?
C16 C11 C12 C13 -0.2(2) . . . . ?
C1 C11 C12 C13 -178.05(14) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C11 -0.3(2) . . . . ?
C12 C11 C16 C15 0.5(2) . . . . ?
C1 C11 C16 C15 178.52(14) . . . . ?
O1 C1 C21 C26 2.31(18) . . . . ?
C11 C1 C21 C26 119.59(14) . . . . ?
C2 C1 C21 C26 -117.50(14) . . . . ?
O1 C1 C21 C22 -179.53(13) . . . . ?
C11 C1 C21 C22 -62.26(16) . . . . ?
C2 C1 C21 C22 60.66(16) . . . . ?
C26 C21 C22 C23 1.0(2) . . . . ?
C1 C21 C22 C23 -177.26(15) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C22 C21 C26 C25 -0.3(2) . . . . ?
C1 C21 C26 C25 177.83(15) . . . . ?
C24 C25 C26 C21 -0.3(3) . . . . ?
C41 C3 C31 C36 126.62(15) . . . . ?
C2 C3 C31 C36 -120.77(15) . . . . ?
C41 C3 C31 C32 -54.08(15) . . . . ?
C2 C3 C31 C32 58.53(15) . . . . ?
C36 C31 C32 C33 1.0(2) . . . . ?
C3 C31 C32 C33 -178.35(13) . . . . ?
C36 C31 C32 C5 179.00(13) . . . . ?
C3 C31 C32 C5 -0.34(17) . . . . ?
C42 C5 C32 C33 -127.72(15) . . . . ?
C4 C5 C32 C33 118.23(16) . . . . ?
C42 C5 C32 C31 54.44(16) . . . . ?
C4 C5 C32 C31 -59.61(15) . . . . ?
C31 C32 C33 C34 -0.4(2) . . . . ?
C5 C32 C33 C34 -178.16(15) . . . . ?
C32 C33 C34 C35 -0.1(3) . . . . ?
C33 C34 C35 C36 0.0(3) . . . . ?
C34 C35 C36 C31 0.5(3) . . . . ?
C32 C31 C36 C35 -1.0(2) . . . . ?
C3 C31 C36 C35 178.26(15) . . . . ?
C31 C3 C41 C46 -127.85(15) . . . . ?
C2 C3 C41 C46 116.62(15) . . . . ?
C31 C3 C41 C42 54.71(15) . . . . ?
C2 C3 C41 C42 -60.82(15) . . . . ?
C46 C41 C42 C43 0.4(2) . . . . ?
C3 C41 C42 C43 178.01(13) . . . . ?
C46 C41 C42 C5 -178.44(13) . . . . ?
C3 C41 C42 C5 -0.82(17) . . . . ?
C32 C5 C42 C43 127.57(17) . . . . ?
C4 C5 C42 C43 -119.07(17) . . . . ?
C32 C5 C42 C41 -53.70(16) . . . . ?
C4 C5 C42 C41 59.66(16) . . . . ?
C41 C42 C43 C44 0.0(2) . . . . ?
C5 C42 C43 C44 178.64(15) . . . . ?
C42 C43 C44 C45 -0.3(3) . . . . ?
C43 C44 C45 C46 0.3(3) . . . . ?
C42 C41 C46 C45 -0.4(2) . . . . ?
C3 C41 C46 C45 -177.72(14) . . . . ?
C44 C45 C46 C41 0.1(2) . . . . ?
C56 C51 C52 C53 1.5(2) . . . . ?
C57 C51 C52 C53 -177.07(18) . . . . ?
C56 C51 C52 C58 -178.04(17) . . . . ?
C57 C51 C52 C58 3.4(3) . . . . ?
C51 C52 C53 C54 -1.0(3) . . . . ?
C58 C52 C53 C54 178.54(18) . . . . ?
C52 C53 C54 C55 -0.5(3) . . . . ?
C53 C54 C55 C56 1.5(3) . . . . ?
C52 C51 C56 C55 -0.5(3) . . . . ?
C57 C51 C56 C55 178.0(2) . . . . ?
C54 C55 C56 C51 -1.0(3) . . . . ?

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
C16 H16 O1 0.95 2.42 2.7517(19) 100 . yes
C26 H26 O1 0.95 2.31 2.679(2) 102 . yes

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.035

