# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_TI-3Q
_audit_block_doi                 10.5517/ccdc.csd.cc1pv9nh
_database_code_depnum_ccdc_archive 'CCDC 1574417'
_audit_update_record             
;
2017-09-14 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_audit_creation_date             2017-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'triptycene tribenzoquinone'
_chemical_name_systematic        
9,10-dihydro-9,10-o-Benzenoanthracene-1,4,5,8,13,16-hexone
_chemical_formula_moiety         'C20 H8 O6'
_chemical_formula_sum            'C20 H8 O6'
_chemical_formula_weight         344.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           109
_space_group_name_H-M_alt        'I 41 m d'
_space_group_name_Hall           'I 4bw -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x, -y, z'
'-x+1/2, y+1/2, z+1/2'
'-y, -x+1/2, z+1/4'
'y+1/2, x, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'x+1/2, -y+1/2, z+1/2'
'-x+1, y+1, z+1'
'-y+1/2, -x+1, z+3/4'
'y+1, x+1/2, z+5/4'

_cell_length_a                   10.8498(4)
_cell_length_b                   10.8498(4)
_cell_length_c                   12.7484(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1500.72(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4244
_cell_measurement_temperature    304.5
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0659 before and 0.0613 after correction. The Ratio of minimum to maximum transmission is 0.9270. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10224
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.236
_diffrn_reflns_theta_min         2.465
_diffrn_ambient_temperature      304.5
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                855
_reflns_number_total             1006
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 355 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         1006
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.4910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O001 O 0.5000 0.7461(2) 0.3639(2) 0.0422(7) Uani 1 2 d S T P . .
O002 O 0.69719(18) 0.74414(17) 0.69559(18) 0.0508(6) Uani 1 1 d . . . . .
C1 C 0.5000 0.5614(4) 0.2685(4) 0.0588(13) Uani 1 2 d S T P . .
H1 H 0.5000 0.6027 0.2046 0.071 Uiso 1 2 calc RS T P . .
C2 C 0.5000 0.6336(3) 0.3654(3) 0.0316(8) Uani 1 2 d S T P . .
C3 C 0.5000 0.5616(3) 0.4635(3) 0.0249(7) Uani 1 2 d S T P . .
C4 C 0.5000 0.6196(3) 0.5723(3) 0.0252(7) Uani 1 2 d S T P . .
H4 H 0.5000 0.7099 0.5722 0.030 Uiso 1 2 calc RS T P . .
C5 C 0.6105(2) 0.5617(2) 0.62773(18) 0.0257(5) Uani 1 1 d . . . . .
C6 C 0.7047(2) 0.6333(2) 0.68427(19) 0.0333(6) Uani 1 1 d . . . . .
C7 C 0.8063(3) 0.5610(3) 0.7314(2) 0.0498(8) Uani 1 1 d . . . . .
H7 H 0.8721 0.6026 0.7619 0.060 Uiso 1 1 calc R . . . .


_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
O001 C2 1.220(4) . ?
O002 C6 1.214(3) . ?
C1 C1 1.332(10) 10_554 ?
C1 H1 0.9300 . ?
C1 C2 1.463(6) . ?
C2 C3 1.475(5) . ?
C3 C3 1.337(6) 10_554 ?
C3 C4 1.522(5) . ?
C4 H4 0.9800 . ?
C4 C5 1.528(3) 14_544 ?
C4 C5 1.528(3) . ?
C5 C5 1.338(4) 5_565 ?
C5 C6 1.472(3) . ?
C6 C7 1.480(4) . ?
C7 C7 1.324(6) 5_565 ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1 H1 118.8 10_554 . ?
C1 C1 C2 122.4(2) 10_554 . ?
C2 C1 H1 118.8 . . ?
O001 C2 C1 121.5(4) . . ?
O001 C2 C3 122.9(3) . . ?
C1 C2 C3 115.6(3) . . ?
C2 C3 C4 123.6(3) . . ?
C3 C3 C2 121.98(19) 10_554 . ?
C3 C3 C4 114.41(17) 10_554 . ?
C3 C4 H4 114.3 . . ?
C3 C4 C5 104.57(19) . 14_544 ?
C3 C4 C5 104.57(19) . . ?
C5 C4 H4 114.3 14_544 . ?
C5 C4 H4 114.3 . . ?
C5 C4 C5 103.5(3) 14_544 . ?
C5 C5 C4 114.30(15) 5_565 . ?
C5 C5 C6 121.86(12) 5_565 . ?
C6 C5 C4 123.7(2) . . ?
O002 C6 C5 122.3(2) . . ?
O002 C6 C7 121.8(2) . . ?
C5 C6 C7 115.8(2) . . ?
C6 C7 H7 119.0 . . ?
C7 C7 C6 122.00(15) 5_565 . ?
C7 C7 H7 119.0 5_565 . ?


_olex2_submission_special_instructions 'No special instructions were received'
