# 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_ka143
_database_code_depnum_ccdc_archive 'CCDC 2077286'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-04-13 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid'
_chemical_name_common            ?
_chemical_melting_point          513.15
_chemical_formula_moiety         'C18 H14 O4, 0.5(C8 H10)'
_chemical_formula_sum            'C22 H19 O4'
_chemical_formula_weight         347.37

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      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                   8.9676(5)
_cell_length_b                   8.9772(4)
_cell_length_c                   11.5304(6)
_cell_angle_alpha                76.582(2)
_cell_angle_beta                 77.282(2)
_cell_angle_gamma                85.623(2)
_cell_volume                     880.44(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7315
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      28.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             366
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.742
_exptl_crystal_size_mid          0.479
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9342
_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            15159
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.857
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4286
_reflns_number_gt                3534
_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 atoms of the hydroxyl groups were allowed to rotate with a fixed angle
around the C---O bonds to best fit the experimental electron density (HFIX 147
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(O).

The solvent molecule is disordered around an inversion point necessitating the
use of various constraints and restraints. The 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)+(0.0434P)²+0.2487P] 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       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4286
_refine_ls_number_parameters     264
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.039
_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 0.80692(9) 0.58540(9) 0.53433(9) 0.0331(2) Uani 1 1 d . . . . .
H1A H 0.899398 0.605816 0.505424 0.050 Uiso 1 1 calc R U . . .
O2 O 0.89953(9) 0.34603(10) 0.56078(9) 0.0367(2) Uani 1 1 d . . . . .
O3 O 0.50421(11) -0.00827(10) 0.65923(8) 0.0353(2) Uani 1 1 d . . . . .
H3A H 0.484632 -0.058122 0.611329 0.053 Uiso 1 1 calc R U . . .
O4 O 0.55245(10) 0.17489(9) 0.48939(8) 0.0325(2) Uani 1 1 d . . . . .
C1 C 0.53782(11) 0.48701(12) 0.70348(9) 0.0210(2) Uani 1 1 d . . . . .
H1 H 0.544555 0.599562 0.667584 0.025 Uiso 1 1 calc R U . . .
C2 C 0.62760(11) 0.38966(12) 0.61259(9) 0.0193(2) Uani 1 1 d . . . . .
H2 H 0.578564 0.410333 0.540284 0.023 Uiso 1 1 calc R U . . .
C3 C 0.61227(12) 0.21761(12) 0.67279(9) 0.0215(2) Uani 1 1 d . . . . .
H3 H 0.717041 0.175353 0.680226 0.026 Uiso 1 1 calc R U . . .
C4 C 0.51302(12) 0.19759(13) 0.80470(10) 0.0247(2) Uani 1 1 d . . . . .
H4 H 0.500838 0.087312 0.847208 0.030 Uiso 1 1 calc R U . . .
C5 C 0.79264(11) 0.43699(12) 0.56772(9) 0.0212(2) Uani 1 1 d . . . . .
C6 C 0.55201(12) 0.12840(12) 0.59735(10) 0.0238(2) Uani 1 1 d . . . . .
C11 C 0.60437(11) 0.44068(13) 0.81694(9) 0.0234(2) Uani 1 1 d . . . . .
C12 C 0.59182(12) 0.28517(13) 0.87082(10) 0.0256(2) Uani 1 1 d . . . . .
C13 C 0.64789(14) 0.22482(16) 0.97521(11) 0.0336(3) Uani 1 1 d . . . . .
H13 H 0.640025 0.118629 1.011866 0.040 Uiso 1 1 calc R U . . .
C14 C 0.71590(15) 0.32141(18) 1.02589(11) 0.0391(3) Uani 1 1 d . . . . .
H14 H 0.753830 0.280838 1.097878 0.047 Uiso 1 1 calc R U . . .
C15 C 0.72870(14) 0.47525(17) 0.97262(11) 0.0360(3) Uani 1 1 d . . . . .
H15 H 0.775818 0.539946 1.007790 0.043 Uiso 1 1 calc R U . . .
C16 C 0.67291(12) 0.53631(15) 0.86750(11) 0.0291(3) Uani 1 1 d . . . . .
H16 H 0.681667 0.642414 0.830731 0.035 Uiso 1 1 calc R U . . .
C21 C 0.37429(12) 0.43382(13) 0.73767(9) 0.0232(2) Uani 1 1 d . . . . .
C22 C 0.36075(12) 0.27841(13) 0.79277(10) 0.0254(2) Uani 1 1 d . . . . .
C23 C 0.21751(14) 0.21344(16) 0.83042(12) 0.0347(3) Uani 1 1 d . . . . .
H23 H 0.207685 0.107503 0.867487 0.042 Uiso 1 1 calc R U . . .
C24 C 0.08858(14) 0.30539(18) 0.81318(13) 0.0407(3) Uani 1 1 d . . . . .
H24 H -0.009797 0.261864 0.838962 0.049 Uiso 1 1 calc R U . . .
C25 C 0.10233(13) 0.45896(17) 0.75905(12) 0.0365(3) Uani 1 1 d . . . . .
H25 H 0.013309 0.520497 0.748252 0.044 Uiso 1 1 calc R U . . .
C26 C 0.24581(12) 0.52494(15) 0.71995(10) 0.0279(2) Uani 1 1 d . . . . .
H26 H 0.255285 0.630595 0.681802 0.033 Uiso 1 1 calc R U . . .
C31 C 1.0245(6) 0.0569(7) 0.3503(6) 0.066(2) Uani 0.5 1 d DG . P A -1
C32 C 1.1318(6) 0.0993(7) 0.4063(6) 0.0677(18) Uani 0.5 1 d G . P A -1
H32 H 1.216068 0.159054 0.358674 0.081 Uiso 0.5 1 calc R U P A -1
C33 C 1.1159(8) 0.0543(8) 0.5321(6) 0.0646(18) Uani 0.5 1 d G . P A -1
H33 H 1.189198 0.083272 0.570391 0.078 Uiso 0.5 1 calc R U P A -1
C34 C 0.9926(9) -0.0331(8) 0.6018(6) 0.079(2) Uani 0.5 1 d DG . P A -1
C35 C 0.8853(8) -0.0755(7) 0.5458(6) 0.078(3) Uani 0.5 1 d G . P A -1
H35 H 0.801038 -0.135192 0.593414 0.094 Uiso 0.5 1 calc R U P A -1
C36 C 0.9012(6) -0.0304(7) 0.4200(6) 0.082(3) Uani 0.5 1 d G . P A -1
H36 H 0.827905 -0.059411 0.381696 0.098 Uiso 0.5 1 calc R U P A -1
C37 C 1.0506(11) 0.1020(14) 0.2101(8) 0.097(3) Uani 0.5 1 d D . P A -1
H37A H 1.159848 0.091858 0.174969 0.146 Uiso 0.5 1 calc R U P A -1
H37B H 1.015729 0.208356 0.184786 0.146 Uiso 0.5 1 calc R U P A -1
H37C H 0.992975 0.034400 0.181524 0.146 Uiso 0.5 1 calc R U P A -1
C38 C 0.9747(13) -0.0868(11) 0.7387(8) 0.099(3) Uani 0.5 1 d D . P A -1
H38A H 0.917349 -0.008708 0.778812 0.148 Uiso 0.5 1 calc R U P A -1
H38B H 1.075997 -0.103428 0.759237 0.148 Uiso 0.5 1 calc R U P A -1
H38C H 0.919365 -0.182837 0.766544 0.148 Uiso 0.5 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3061(13) . ?
O1 H1A 0.8400 . ?
O2 C5 1.2120(13) . ?
O3 C6 1.3181(13) . ?
O3 H3A 0.8400 . ?
O4 C6 1.2168(14) . ?
C1 C11 1.5146(15) . ?
C1 C21 1.5162(14) . ?
C1 C2 1.5673(14) . ?
C1 H1 1.0000 . ?
C2 C5 1.5151(14) . ?
C2 C3 1.5424(14) . ?
C2 H2 1.0000 . ?
C3 C6 1.5121(14) . ?
C3 C4 1.5618(15) . ?
C3 H3 1.0000 . ?
C4 C22 1.5149(16) . ?
C4 C12 1.5161(15) . ?
C4 H4 1.0000 . ?
C11 C16 1.3876(15) . ?
C11 C12 1.3922(16) . ?
C12 C13 1.3848(16) . ?
C13 C14 1.3921(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3916(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.3858(16) . ?
C21 C22 1.3948(16) . ?
C22 C23 1.3892(15) . ?
C23 C24 1.392(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.3952(16) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.3900 . ?
C31 C36 1.3900 . ?
C31 C37 1.541(8) . ?
C32 C33 1.3900 . ?
C32 H32 0.9500 . ?
C33 C34 1.3900 . ?
C33 H33 0.9500 . ?
C34 C35 1.3900 . ?
C34 C38 1.515(9) . ?
C35 C36 1.3900 . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 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
C5 O1 H1A 109.5 . . ?
C6 O3 H3A 109.5 . . ?
C11 C1 C21 107.48(8) . . ?
C11 C1 C2 106.20(8) . . ?
C21 C1 C2 106.21(8) . . ?
C11 C1 H1 112.2 . . ?
C21 C1 H1 112.2 . . ?
C2 C1 H1 112.2 . . ?
C5 C2 C3 112.71(8) . . ?
C5 C2 C1 111.19(8) . . ?
C3 C2 C1 109.72(8) . . ?
C5 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
C6 C3 C2 112.86(9) . . ?
C6 C3 C4 112.23(8) . . ?
C2 C3 C4 109.56(8) . . ?
C6 C3 H3 107.3 . . ?
C2 C3 H3 107.3 . . ?
C4 C3 H3 107.3 . . ?
C22 C4 C12 107.47(9) . . ?
C22 C4 C3 106.62(9) . . ?
C12 C4 C3 106.16(8) . . ?
C22 C4 H4 112.1 . . ?
C12 C4 H4 112.1 . . ?
C3 C4 H4 112.1 . . ?
O2 C5 O1 123.78(10) . . ?
O2 C5 C2 123.25(9) . . ?
O1 C5 C2 112.94(9) . . ?
O4 C6 O3 123.03(10) . . ?
O4 C6 C3 123.80(10) . . ?
O3 C6 C3 113.12(9) . . ?
C16 C11 C12 120.27(11) . . ?
C16 C11 C1 126.50(11) . . ?
C12 C11 C1 113.23(9) . . ?
C13 C12 C11 120.19(11) . . ?
C13 C12 C4 126.32(11) . . ?
C11 C12 C4 113.49(9) . . ?
C12 C13 C14 119.30(12) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.62(12) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.28(11) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 119.34(12) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C26 C21 C22 120.64(10) . . ?
C26 C21 C1 125.90(10) . . ?
C22 C21 C1 113.45(9) . . ?
C23 C22 C21 120.03(11) . . ?
C23 C22 C4 126.81(11) . . ?
C21 C22 C4 113.16(9) . . ?
C22 C23 C24 119.22(12) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 120.59(11) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.60(12) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 118.91(12) . . ?
C21 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C32 C31 C36 120.0 . . ?
C32 C31 C37 118.4(4) . . ?
C36 C31 C37 121.5(4) . . ?
C31 C32 C33 120.0 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 C35 120.0 . . ?
C33 C34 C38 121.0(6) . . ?
C35 C34 C38 119.0(6) . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C31 120.0 . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
C31 C37 H37A 109.5 . . ?
C31 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C31 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
C11 C1 C2 C5 -67.97(10) . . . . ?
C21 C1 C2 C5 177.82(8) . . . . ?
C11 C1 C2 C3 57.39(10) . . . . ?
C21 C1 C2 C3 -56.83(10) . . . . ?
C5 C2 C3 C6 -110.00(10) . . . . ?
C1 C2 C3 C6 125.52(9) . . . . ?
C5 C2 C3 C4 124.17(9) . . . . ?
C1 C2 C3 C4 -0.31(11) . . . . ?
C6 C3 C4 C22 -68.80(11) . . . . ?
C2 C3 C4 C22 57.39(10) . . . . ?
C6 C3 C4 C12 176.83(9) . . . . ?
C2 C3 C4 C12 -56.98(11) . . . . ?
C3 C2 C5 O2 11.93(14) . . . . ?
C1 C2 C5 O2 135.59(11) . . . . ?
C3 C2 C5 O1 -169.87(9) . . . . ?
C1 C2 C5 O1 -46.20(12) . . . . ?
C2 C3 C6 O4 17.86(15) . . . . ?
C4 C3 C6 O4 142.24(11) . . . . ?
C2 C3 C6 O3 -164.71(9) . . . . ?
C4 C3 C6 O3 -40.33(13) . . . . ?
C21 C1 C11 C16 -125.86(11) . . . . ?
C2 C1 C11 C16 120.79(11) . . . . ?
C21 C1 C11 C12 54.28(11) . . . . ?
C2 C1 C11 C12 -59.07(11) . . . . ?
C16 C11 C12 C13 -0.09(16) . . . . ?
C1 C11 C12 C13 179.77(10) . . . . ?
C16 C11 C12 C4 179.54(9) . . . . ?
C1 C11 C12 C4 -0.60(13) . . . . ?
C22 C4 C12 C13 125.88(12) . . . . ?
C3 C4 C12 C13 -120.33(12) . . . . ?
C22 C4 C12 C11 -53.72(12) . . . . ?
C3 C4 C12 C11 60.07(12) . . . . ?
C11 C12 C13 C14 0.39(17) . . . . ?
C4 C12 C13 C14 -179.19(11) . . . . ?
C12 C13 C14 C15 -0.51(18) . . . . ?
C13 C14 C15 C16 0.33(19) . . . . ?
C12 C11 C16 C15 -0.09(16) . . . . ?
C1 C11 C16 C15 -179.94(10) . . . . ?
C14 C15 C16 C11 -0.03(17) . . . . ?
C11 C1 C21 C26 125.53(11) . . . . ?
C2 C1 C21 C26 -121.14(11) . . . . ?
C11 C1 C21 C22 -53.65(11) . . . . ?
C2 C1 C21 C22 59.68(11) . . . . ?
C26 C21 C22 C23 0.06(16) . . . . ?
C1 C21 C22 C23 179.29(10) . . . . ?
C26 C21 C22 C4 -179.85(9) . . . . ?
C1 C21 C22 C4 -0.63(13) . . . . ?
C12 C4 C22 C23 -125.63(12) . . . . ?
C3 C4 C22 C23 120.89(12) . . . . ?
C12 C4 C22 C21 54.28(12) . . . . ?
C3 C4 C22 C21 -59.20(11) . . . . ?
C21 C22 C23 C24 -0.44(18) . . . . ?
C4 C22 C23 C24 179.46(11) . . . . ?
C22 C23 C24 C25 0.24(19) . . . . ?
C23 C24 C25 C26 0.34(19) . . . . ?
C22 C21 C26 C25 0.51(16) . . . . ?
C1 C21 C26 C25 -178.61(10) . . . . ?
C24 C25 C26 C21 -0.71(17) . . . . ?
C36 C31 C32 C33 0.0 . . . . ?
C37 C31 C32 C33 -176.9(6) . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C32 C33 C34 C38 178.5(7) . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C38 C34 C35 C36 -178.6(6) . . . . ?
C34 C35 C36 C31 0.0 . . . . ?
C32 C31 C36 C35 0.0 . . . . ?
C37 C31 C36 C35 176.8(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A O2 0.84 1.84 2.6785(11) 179 2_766 yes
O3 H3A O4 0.84 1.83 2.6686(11) 177 2_656 yes
C2 H2 O4 1.00 2.36 2.8426(12) 109 . yes
C3 H3 O2 1.00 2.31 2.8161(13) 110 . yes

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_ka081
_database_code_depnum_ccdc_archive 'CCDC 2077287'
loop_
_audit_author_name
_audit_author_address
'Eric Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'dimethyl-trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate   1,4-xylene'
_chemical_name_common            ?
_chemical_melting_point          381.15
_chemical_formula_moiety         'C20 H18 O4, 0.333(C8 H10)'
_chemical_formula_sum            'C22.67 H21.33 O4'
_chemical_formula_weight         357.73

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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   21.1712(15)
_cell_length_b                   15.3453(8)
_cell_length_c                   11.4218(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3710.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9871
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.05

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             1515
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.707
_exptl_crystal_size_mid          0.338
_exptl_crystal_size_min          0.246
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9334
_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            67112
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.924
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4625
_reflns_number_gt                3563
_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 non-disordered 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
1.5 Ueq(C). The H atoms of the disordered methyl groups were placed in
calculated positions (HFIX 33).

The solvent molecule is extensively disordered around symmetry elements
necessitating the use of various constraints and restraints. The phenyl ring was
forced into a regular hexagon with bond lengths 1.39 Å (AFIX 66 in the SHELXL
program (Sheldrick, 2015)).,Disorder
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0753P)²+2.4935P] 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         4625
_refine_ls_number_parameters     237
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1441
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39069(6) 0.41743(9) 0.14937(11) 0.0362(3) Uani 1 1 d . . . . .
O2 O 0.41223(6) 0.51634(9) 0.28697(12) 0.0446(4) Uani 1 1 d . . . . .
O3 O 0.23653(6) 0.55211(8) 0.53956(11) 0.0367(3) Uani 1 1 d . . . . .
O4 O 0.21988(8) 0.55584(11) 0.34665(12) 0.0563(4) Uani 1 1 d . . . . .
C1 C 0.30385(7) 0.39711(10) 0.51672(13) 0.0251(3) Uani 1 1 d . . . . .
H1 H 0.300968 0.420168 0.598436 0.030 Uiso 1 1 calc R U . . .
C2 C 0.31184(8) 0.33062(10) 0.30817(14) 0.0277(3) Uani 1 1 d . . . . .
H2 H 0.314514 0.302693 0.229226 0.033 Uiso 1 1 calc R U . . .
C3 C 0.31595(7) 0.43229(10) 0.30101(13) 0.0258(3) Uani 1 1 d . . . . .
H3 H 0.280965 0.453590 0.249613 0.031 Uiso 1 1 calc R U . . .
C4 C 0.30702(7) 0.47185(10) 0.42397(13) 0.0254(3) Uani 1 1 d . . . . .
H4 H 0.344973 0.508304 0.441786 0.030 Uiso 1 1 calc R U . . .
C5 C 0.37832(8) 0.46078(10) 0.24785(14) 0.0275(3) Uani 1 1 d . . . . .
C6 C 0.44968(8) 0.43808(13) 0.09157(17) 0.0388(4) Uani 1 1 d . . . . .
H6A H 0.449724 0.412860 0.012747 0.058 Uiso 1 1 calc R U . . .
H6B H 0.484902 0.413880 0.136755 0.058 Uiso 1 1 calc R U . . .
H6C H 0.454337 0.501491 0.086088 0.058 Uiso 1 1 calc R U . . .
C7 C 0.24951(9) 0.53028(10) 0.42918(14) 0.0305(3) Uani 1 1 d . . . . .
C8 C 0.18557(12) 0.61277(15) 0.5570(2) 0.0572(6) Uani 1 1 d . . . . .
H8A H 0.198064 0.670308 0.527887 0.086 Uiso 1 1 calc R U . . .
H8B H 0.175774 0.616662 0.640712 0.086 Uiso 1 1 calc R U . . .
H8C H 0.148154 0.592637 0.514346 0.086 Uiso 1 1 calc R U . . .
C11 C 0.24655(7) 0.34338(10) 0.48379(13) 0.0255(3) Uani 1 1 d . . . . .
C12 C 0.25071(8) 0.30816(10) 0.37103(14) 0.0270(3) Uani 1 1 d . . . . .
C13 C 0.20255(8) 0.25560(11) 0.32827(15) 0.0336(4) Uani 1 1 d . . . . .
H13 H 0.205249 0.231503 0.251825 0.040 Uiso 1 1 calc R U . . .
C14 C 0.15042(9) 0.23864(13) 0.39838(17) 0.0399(4) Uani 1 1 d . . . . .
H14 H 0.117628 0.201919 0.370276 0.048 Uiso 1 1 calc R U . . .
C15 C 0.14594(8) 0.27500(13) 0.50918(16) 0.0379(4) Uani 1 1 d . . . . .
H15 H 0.109730 0.263653 0.555891 0.046 Uiso 1 1 calc R U . . .
C16 C 0.19384(8) 0.32789(11) 0.55279(15) 0.0311(4) Uani 1 1 d . . . . .
H16 H 0.190496 0.352990 0.628566 0.037 Uiso 1 1 calc R U . . .
C21 C 0.36150(7) 0.33979(10) 0.49944(14) 0.0267(3) Uani 1 1 d . . . . .
C22 C 0.36522(8) 0.30283(10) 0.38741(15) 0.0283(3) Uani 1 1 d . . . . .
C23 C 0.41410(8) 0.24651(12) 0.35920(18) 0.0367(4) Uani 1 1 d . . . . .
H23 H 0.417017 0.222349 0.282807 0.044 Uiso 1 1 calc R U . . .
C24 C 0.45877(9) 0.22577(13) 0.4439(2) 0.0438(5) Uani 1 1 d . . . . .
H24 H 0.491865 0.186171 0.425806 0.053 Uiso 1 1 calc R U . . .
C25 C 0.45531(9) 0.26247(13) 0.5542(2) 0.0426(5) Uani 1 1 d . . . . .
H25 H 0.486338 0.248173 0.611128 0.051 Uiso 1 1 calc R U . . .
C26 C 0.40697(8) 0.32007(11) 0.58298(16) 0.0336(4) Uani 1 1 d . . . . .
H26 H 0.405111 0.345548 0.658702 0.040 Uiso 1 1 calc R U . . .
C31 C -0.0220(5) 0.4867(6) 0.2453(8) 0.1410(18) Uani 0.3333 1 d DG U P A -1
C32 C -0.0675(4) 0.5144(7) 0.3249(9) 0.1410(18) Uani 0.3333 1 d DG U P A -1
H32 H -0.108429 0.530034 0.298231 0.169 Uiso 0.3333 1 calc R U P A -1
C33 C -0.0530(4) 0.5192(8) 0.4434(9) 0.1410(18) Uani 0.3333 1 d DG U P A -1
H33 H -0.084030 0.538108 0.497752 0.169 Uiso 0.3333 1 calc R U P A -1
C34 C 0.0070(5) 0.4963(11) 0.4823(8) 0.1410(18) Uani 0.3333 1 d DG U P A -1
C35 C 0.0524(5) 0.4686(10) 0.4028(9) 0.1410(18) Uani 0.3333 1 d DG U P A -1
H35 H 0.093395 0.452941 0.429432 0.169 Uiso 0.3333 1 calc R U P A -1
C36 C 0.0379(5) 0.4638(6) 0.2843(9) 0.1410(18) Uani 0.3333 1 d DG U P A -1
H36 H 0.068997 0.444867 0.229909 0.169 Uiso 0.3333 1 calc R U P A -1
C37 C -0.0389(8) 0.4774(14) 0.1112(15) 0.1410(18) Uani 0.3333 1 d D U P A -1
H37A H -0.001591 0.457358 0.068082 0.211 Uiso 0.3333 1 calc R U P A -1
H37B H -0.073166 0.435101 0.101783 0.211 Uiso 0.3333 1 calc R U P A -1
H37C H -0.052346 0.534090 0.080451 0.211 Uiso 0.3333 1 calc R U P A -1
C38 C 0.0241(6) 0.5019(11) 0.6092(13) 0.1410(18) Uani 0.3333 1 d D U P A -1
H38A H 0.067953 0.483281 0.619927 0.211 Uiso 0.3333 1 calc R U P A -1
H38B H 0.019329 0.562216 0.636091 0.211 Uiso 0.3333 1 calc R U P A -1
H38C H -0.003916 0.463955 0.654725 0.211 Uiso 0.3333 1 calc R U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.333(2) . ?
O1 C6 1.448(2) . ?
O2 C5 1.201(2) . ?
O3 C7 1.333(2) . ?
O3 C8 1.439(2) . ?
O4 C7 1.198(2) . ?
C1 C11 1.514(2) . ?
C1 C21 1.517(2) . ?
C1 C4 1.563(2) . ?
C1 H1 1.0000 . ?
C2 C22 1.509(2) . ?
C2 C12 1.520(2) . ?
C2 C3 1.565(2) . ?
C2 H2 1.0000 . ?
C3 C5 1.518(2) . ?
C3 C4 1.542(2) . ?
C3 H3 1.0000 . ?
C4 C7 1.513(2) . ?
C4 H4 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 C16 1.387(2) . ?
C11 C12 1.399(2) . ?
C12 C13 1.389(2) . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.389(2) . ?
C21 C22 1.402(2) . ?
C22 C23 1.386(2) . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.3900 . ?
C31 C36 1.3900 . ?
C31 C37 1.579(14) . ?
C32 C33 1.3900 . ?
C32 H32 0.9500 . ?
C33 C34 1.3900 . ?
C33 H33 0.9500 . ?
C34 C35 1.3900 . ?
C34 C38 1.496(16) . ?
C35 C36 1.3900 . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 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
C5 O1 C6 116.42(14) . . ?
C7 O3 C8 116.63(15) . . ?
C11 C1 C21 107.24(12) . . ?
C11 C1 C4 105.40(12) . . ?
C21 C1 C4 107.63(12) . . ?
C11 C1 H1 112.1 . . ?
C21 C1 H1 112.1 . . ?
C4 C1 H1 112.1 . . ?
C22 C2 C12 106.88(13) . . ?
C22 C2 C3 105.75(12) . . ?
C12 C2 C3 107.35(13) . . ?
C22 C2 H2 112.2 . . ?
C12 C2 H2 112.2 . . ?
C3 C2 H2 112.2 . . ?
C5 C3 C4 110.96(13) . . ?
C5 C3 C2 110.89(13) . . ?
C4 C3 C2 109.77(12) . . ?
C5 C3 H3 108.4 . . ?
C4 C3 H3 108.4 . . ?
C2 C3 H3 108.4 . . ?
C7 C4 C3 111.58(13) . . ?
C7 C4 C1 111.94(13) . . ?
C3 C4 C1 109.50(12) . . ?
C7 C4 H4 107.9 . . ?
C3 C4 H4 107.9 . . ?
C1 C4 H4 107.9 . . ?
O2 C5 O1 123.43(15) . . ?
O2 C5 C3 125.16(15) . . ?
O1 C5 C3 111.39(13) . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 O3 123.63(17) . . ?
O4 C7 C4 125.75(16) . . ?
O3 C7 C4 110.60(13) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C16 C11 C12 120.49(15) . . ?
C16 C11 C1 126.64(15) . . ?
C12 C11 C1 112.86(13) . . ?
C13 C12 C11 120.12(15) . . ?
C13 C12 C2 126.22(15) . . ?
C11 C12 C2 113.62(14) . . ?
C12 C13 C14 119.32(16) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.37(17) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.78(16) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 118.89(16) . . ?
C11 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C26 C21 C22 120.00(15) . . ?
C26 C21 C1 126.48(15) . . ?
C22 C21 C1 113.48(14) . . ?
C23 C22 C21 120.42(16) . . ?
C23 C22 C2 126.57(16) . . ?
C21 C22 C2 113.01(14) . . ?
C22 C23 C24 119.29(18) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 120.33(17) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.87(18) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C21 C26 C25 119.07(17) . . ?
C21 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C32 C31 C36 120.0 . . ?
C32 C31 C37 120.3(6) . . ?
C36 C31 C37 119.6(6) . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C35 120.0 . . ?
C33 C34 C38 121.1(7) . . ?
C35 C34 C38 118.9(7) . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C31 120.0 . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
C31 C37 H37A 109.5 . . ?
C31 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C31 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
C22 C2 C3 C5 61.65(16) . . . . ?
C12 C2 C3 C5 175.49(12) . . . . ?
C22 C2 C3 C4 -61.30(16) . . . . ?
C12 C2 C3 C4 52.54(16) . . . . ?
C5 C3 C4 C7 118.44(15) . . . . ?
C2 C3 C4 C7 -118.65(14) . . . . ?
C5 C3 C4 C1 -117.07(14) . . . . ?
C2 C3 C4 C1 5.85(17) . . . . ?
C11 C1 C4 C7 62.61(16) . . . . ?
C21 C1 C4 C7 176.82(13) . . . . ?
C11 C1 C4 C3 -61.68(15) . . . . ?
C21 C1 C4 C3 52.53(16) . . . . ?
C6 O1 C5 O2 2.3(2) . . . . ?
C6 O1 C5 C3 -179.00(14) . . . . ?
C4 C3 C5 O2 -10.3(2) . . . . ?
C2 C3 C5 O2 -132.55(17) . . . . ?
C4 C3 C5 O1 171.09(13) . . . . ?
C2 C3 C5 O1 48.82(17) . . . . ?
C8 O3 C7 O4 -2.8(3) . . . . ?
C8 O3 C7 C4 175.68(16) . . . . ?
C3 C4 C7 O4 -11.9(3) . . . . ?
C1 C4 C7 O4 -135.04(19) . . . . ?
C3 C4 C7 O3 169.68(13) . . . . ?
C1 C4 C7 O3 46.56(18) . . . . ?
C21 C1 C11 C16 125.50(17) . . . . ?
C4 C1 C11 C16 -120.02(17) . . . . ?
C21 C1 C11 C12 -54.64(17) . . . . ?
C4 C1 C11 C12 59.83(16) . . . . ?
C16 C11 C12 C13 -1.5(2) . . . . ?
C1 C11 C12 C13 178.64(15) . . . . ?
C16 C11 C12 C2 -179.32(14) . . . . ?
C1 C11 C12 C2 0.82(19) . . . . ?
C22 C2 C12 C13 -123.39(17) . . . . ?
C3 C2 C12 C13 123.53(17) . . . . ?
C22 C2 C12 C11 54.27(17) . . . . ?
C3 C2 C12 C11 -58.81(17) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C2 C12 C13 C14 177.65(16) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C12 C11 C16 C15 1.6(2) . . . . ?
C1 C11 C16 C15 -178.54(15) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C11 C1 C21 C26 -124.16(17) . . . . ?
C4 C1 C21 C26 122.86(17) . . . . ?
C11 C1 C21 C22 53.57(17) . . . . ?
C4 C1 C21 C22 -59.40(16) . . . . ?
C26 C21 C22 C23 0.0(2) . . . . ?
C1 C21 C22 C23 -177.87(14) . . . . ?
C26 C21 C22 C2 179.54(14) . . . . ?
C1 C21 C22 C2 1.64(19) . . . . ?
C12 C2 C22 C23 124.13(17) . . . . ?
C3 C2 C22 C23 -121.70(17) . . . . ?
C12 C2 C22 C21 -55.35(17) . . . . ?
C3 C2 C22 C21 58.82(17) . . . . ?
C21 C22 C23 C24 1.2(2) . . . . ?
C2 C22 C23 C24 -178.27(16) . . . . ?
C22 C23 C24 C25 -1.5(3) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
C22 C21 C26 C25 -0.9(2) . . . . ?
C1 C21 C26 C25 176.66(15) . . . . ?
C24 C25 C26 C21 0.7(3) . . . . ?
C36 C31 C32 C33 0.0 . . . . ?
C37 C31 C32 C33 177.5(10) . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C32 C33 C34 C38 179.2(14) . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C38 C34 C35 C36 -179.2(13) . . . . ?
C34 C35 C36 C31 0.0 . . . . ?
C32 C31 C36 C35 0.0 . . . . ?
C37 C31 C36 C35 -177.6(10) . . . . ?

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 H3 O4 1.00 2.32 2.829(2) 111 . yes
C3 H3 O3 1.00 2.58 3.435(2) 144 7_565 yes
C4 H4 O2 1.00 2.27 2.806(2) 112 . yes
C26 H26 O2 0.95 2.58 3.427(2) 149 7_566 yes

_refine_diff_density_max         0.629
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,4-xylene'
