# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_c18007
_database_code_depnum_ccdc_archive 'CCDC 2040902'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;University of Kentucky
United States of America
;
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2017). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2021-01-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT097_c18007              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.01 eA-3
RESPONSE: May be associated with trace impurity or whole-molecule disorder, but is too small to model so very minor.
;
# Added during the CSD deposition process: Tuesday 27 October 2020 05:06 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/1

_shelx_SHELXL_version_number     2018/1

_chemical_name_systematic        'contorted tetrabenzofuranylbenzocoronene'
_chemical_name_common            cTBFBC
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H22 O4'
_chemical_formula_sum            'C52 H22 O4'
_chemical_formula_weight         710.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   48.653(6)
_cell_length_b                   4.5798(6)
_cell_length_c                   30.036(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.401(18)
_cell_angle_gamma                90
_cell_volume                     6273.0(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    4794
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      68.07

_exptl_crystal_description       lath
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             2928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.002
_exptl_absorpt_coefficient_mu    0.753
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on a looped nylon fibre. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 5.6
_diffrn_reflns_number            29255
_diffrn_reflns_av_unetI/netI     0.1202
_diffrn_reflns_av_R_equivalents  0.1368
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.061
_diffrn_reflns_theta_max         68.530
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996

_reflns_number_total             5744
_reflns_number_gt                3224
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
; 
Reflections were merged by SHELXL according to the crystal 
class for the calculation of statistics and refinement. 
 
_reflns_Friedel_fraction is defined as the number of unique 
Friedel pairs measured divided by the number that would be 
possible theoretically, ignoring centric projections and 
systematic absences. 
;

_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1486P)²+4.5268P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5744
_refine_ls_number_parameters     505
_refine_ls_number_restraints     561
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0856
_refine_ls_wR_factor_ref         0.2843
_refine_ls_wR_factor_gt          0.2290
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      0.986
_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 0.65427(7) -0.1207(7) 0.1857(1) 0.0453(7) Uani 1 1 d . . . . .
O2 O 0.60823(7) 0.2343(7) 0.13267(12) 0.0530(8) Uani 1 1 d . . . . .
O3 O 0.61606(7) 0.3818(7) 0.47085(11) 0.0492(8) Uani 1 1 d . . . . .
O4 O 0.57306(8) 0.7817(8) 0.41814(13) 0.0636(10) Uani 1 1 d . . . . .
C1 C 0.69055(10) -0.0209(9) 0.35721(16) 0.0434(10) Uani 1 1 d . . . . .
C2 C 0.71977(10) -0.0824(10) 0.36139(17) 0.0462(10) Uani 1 1 d . . . . .
H2 H 0.724063 -0.121314 0.333439 0.055 Uiso 1 1 calc R U . . .
C3 C 0.74217(11) -0.0878(12) 0.40450(18) 0.0547(12) Uani 1 1 d . . . . .
H3 H 0.761413 -0.141299 0.406424 0.066 Uiso 1 1 calc R U . . .
C4 C 0.73643(11) -0.0135(11) 0.44580(18) 0.0539(12) Uani 1 1 d . . . . .
H4 H 0.751873 -0.013328 0.475751 0.065 Uiso 1 1 calc R U . . .
C5 C 0.70866(11) 0.0583(11) 0.44275(18) 0.0508(11) Uani 1 1 d . . . . .
H5 H 0.705082 0.112401 0.470787 0.061 Uiso 1 1 calc R U . . .
C6 C 0.68481(10) 0.0545(9) 0.39858(16) 0.0426(10) Uani 1 1 d . . . . .
C7 C 0.65631(10) 0.1628(9) 0.39452(16) 0.0408(9) Uani 1 1 d . . . . .
C8 C 0.63787(9) 0.2750(9) 0.35032(15) 0.0391(9) Uani 1 1 d . . . . .
C9 C 0.61358(10) 0.4555(9) 0.34666(16) 0.0427(10) Uani 1 1 d . . . . .
C10 C 0.5957(1) 0.5848(9) 0.30208(16) 0.0430(10) Uani 1 1 d . . . . .
C11 C 0.57295(10) 0.7839(10) 0.29907(19) 0.0500(11) Uani 1 1 d . . . . .
C12 C 0.55632(11) 0.9091(10) 0.25468(19) 0.0540(12) Uani 1 1 d . . . . .
H12 H 0.542005 1.053972 0.252944 0.065 Uiso 1 1 calc R U . . .
C13 C 0.56091(10) 0.8216(10) 0.21470(19) 0.0517(11) Uani 1 1 d . . . . .
H13 H 0.549072 0.902358 0.185093 0.062 Uiso 1 1 calc R U . . .
C14 C 0.58224(10) 0.6182(10) 0.21537(17) 0.0477(10) Uani 1 1 d . . . . .
C15 C 0.60079(10) 0.4987(9) 0.25957(16) 0.0424(10) Uani 1 1 d . . . . .
C16 C 0.62369(9) 0.2983(9) 0.26265(16) 0.0409(9) Uani 1 1 d . . . . .
C17 C 0.64334(9) 0.1922(9) 0.30743(15) 0.0384(9) Uani 1 1 d . . . . .
C18 C 0.66735(9) 0.0130(9) 0.31093(15) 0.0387(9) Uani 1 1 d . . . . .
C19 C 0.66912(10) -0.1076(9) 0.26773(16) 0.0410(9) Uani 1 1 d . . . . .
C20 C 0.6874(1) -0.3192(9) 0.25453(16) 0.0418(10) Uani 1 1 d . . . . .
C21 C 0.70934(10) -0.5185(10) 0.27652(18) 0.0482(11) Uani 1 1 d . . . . .
H21 H 0.716339 -0.539971 0.310079 0.058 Uiso 1 1 calc R U . . .
C22 C 0.72109(11) -0.6882(10) 0.24870(18) 0.0506(11) Uani 1 1 d . . . . .
H22 H 0.736204 -0.824201 0.263826 0.061 Uiso 1 1 calc R U . . .
C23 C 0.71123(11) -0.6626(10) 0.19969(19) 0.0533(11) Uani 1 1 d . . . . .
H23 H 0.719979 -0.776966 0.181823 0.064 Uiso 1 1 calc R U . . .
C24 C 0.68898(11) -0.4736(10) 0.17679(18) 0.0503(11) Uani 1 1 d . . . . .
H24 H 0.681754 -0.456673 0.143162 0.060 Uiso 1 1 calc R U . . .
C25 C 0.67752(10) -0.3096(10) 0.20443(16) 0.0432(10) Uani 1 1 d . . . . .
C26 C 0.6497(1) 0.0000(9) 0.22477(16) 0.0413(9) Uani 1 1 d . . . . .
C27 C 0.62746(9) 0.2009(9) 0.21966(16) 0.0405(9) Uani 1 1 d . . . . .
C28 C 0.60779(10) 0.3179(10) 0.17662(16) 0.0465(10) Uani 1 1 d . . . . .
C29 C 0.58485(11) 0.3839(11) 0.09959(18) 0.0534(11) Uani 1 1 d . . . . .
C30 C 0.57725(12) 0.3507(13) 0.05132(19) 0.0608(13) Uani 1 1 d . . . . .
H30 H 0.587727 0.228260 0.037268 0.073 Uiso 1 1 calc R U . . .
C31 C 0.55265(13) 0.5139(13) 0.0247(2) 0.0670(14) Uani 1 1 d . . . . .
H31 H 0.545867 0.496483 -0.008914 0.080 Uiso 1 1 calc R U . . .
C32 C 0.53789(13) 0.6968(12) 0.0445(2) 0.0640(14) Uani 1 1 d . . . . .
H32 H 0.521680 0.806953 0.024704 0.077 Uiso 1 1 calc R U . . .
C33 C 0.54674(12) 0.7212(12) 0.0940(2) 0.0605(13) Uani 1 1 d . . . . .
H33 H 0.536313 0.845014 0.107955 0.073 Uiso 1 1 calc R U . . .
C34 C 0.57084(10) 0.5635(10) 0.12264(16) 0.0462(10) Uani 1 1 d . . . . .
C35 C 0.58639(11) 0.5115(10) 0.17295(17) 0.0497(11) Uani 1 1 d . . . . .
C36 C 0.64665(10) 0.1933(9) 0.43461(16) 0.0416(9) Uani 1 1 d . . . . .
C37 C 0.65435(10) 0.0650(9) 0.48174(16) 0.0445(10) Uani 1 1 d . . . . .
C38 C 0.6735(1) -0.1504(10) 0.50872(16) 0.0475(10) Uani 1 1 d . . . . .
H38 H 0.686433 -0.249607 0.496371 0.057 Uiso 1 1 calc R U . . .
C39 C 0.67328(11) -0.2158(11) 0.55343(18) 0.0510(11) Uani 1 1 d . . . . .
H39 H 0.686232 -0.361518 0.571693 0.061 Uiso 1 1 calc R U . . .
C40 C 0.65453(11) -0.0738(11) 0.57264(18) 0.0539(12) Uani 1 1 d . . . . .
H40 H 0.655248 -0.120619 0.603833 0.065 Uiso 1 1 calc R U . . .
C41 C 0.63520(11) 0.1317(11) 0.54685(17) 0.0523(11) Uani 1 1 d . . . . .
H41 H 0.622211 0.228524 0.559352 0.063 Uiso 1 1 calc R U . . .
C42 C 0.63526(11) 0.1938(10) 0.50175(17) 0.0469(10) Uani 1 1 d . . . . .
C43 C 0.62318(10) 0.3717(9) 0.43009(16) 0.0436(10) Uani 1 1 d . . . . .
C44 C 0.60649(10) 0.5204(9) 0.38837(16) 0.044(1) Uani 1 1 d . . . . .
C45 C 0.58309(11) 0.712(1) 0.38277(19) 0.0519(11) Uani 1 1 d . . . . .
C46 C 0.54912(13) 0.9696(12) 0.3979(2) 0.0636(13) Uani 1 1 d . . . . .
C47 C 0.53261(14) 1.0818(14) 0.4220(2) 0.0746(16) Uani 1 1 d . . . . .
H47 H 0.536110 1.035792 0.454375 0.089 Uiso 1 1 calc R U . . .
C48 C 0.51048(14) 1.2667(13) 0.3965(2) 0.0747(16) Uani 1 1 d . . . . .
H48 H 0.498638 1.351174 0.412420 0.090 Uiso 1 1 calc R U . . .
C49 C 0.50426(13) 1.3378(14) 0.3496(2) 0.0698(15) Uani 1 1 d . . . . .
H49 H 0.488472 1.465211 0.333701 0.084 Uiso 1 1 calc R U . . .
C50 C 0.52222(13) 1.2150(12) 0.3251(2) 0.0697(15) Uani 1 1 d . . . . .
H50 H 0.518710 1.259575 0.292648 0.084 Uiso 1 1 calc R U . . .
C51 C 0.54521(10) 1.0261(10) 0.35072(17) 0.0472(10) Uani 1 1 d . . . . .
C52 C 0.5671(1) 0.8487(10) 0.34142(19) 0.0497(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C25 1.379(6) . ?
O1 C26 1.383(5) . ?
O2 C28 1.382(5) . ?
O2 C29 1.401(6) . ?
O3 C42 1.368(6) . ?
O3 C43 1.384(5) . ?
O4 C45 1.353(6) . ?
O4 C46 1.405(7) . ?
C1 C6 1.408(6) . ?
C1 C2 1.411(6) . ?
C1 C18 1.462(6) . ?
C2 C3 1.372(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.405(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.363(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.426(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.437(6) . ?
C7 C8 1.415(6) . ?
C7 C36 1.444(6) . ?
C8 C9 1.415(6) . ?
C8 C17 1.454(6) . ?
C9 C44 1.442(6) . ?
C9 C10 1.445(6) . ?
C10 C11 1.412(6) . ?
C10 C15 1.438(6) . ?
C11 C12 1.417(7) . ?
C11 C52 1.429(7) . ?
C12 C13 1.356(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.429(6) . ?
C14 C35 1.443(7) . ?
C15 C16 1.421(6) . ?
C16 C17 1.436(6) . ?
C16 C27 1.437(6) . ?
C17 C18 1.401(6) . ?
C18 C19 1.440(6) . ?
C19 C26 1.397(6) . ?
C19 C20 1.461(6) . ?
C20 C21 1.385(7) . ?
C20 C25 1.412(6) . ?
C21 C22 1.401(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.369(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(6) . ?
C24 H24 0.9500 . ?
C26 C27 1.388(6) . ?
C27 C28 1.418(6) . ?
C28 C35 1.342(7) . ?
C29 C30 1.374(7) . ?
C29 C34 1.396(7) . ?
C30 C31 1.401(8) . ?
C30 H30 0.9500 . ?
C31 C32 1.366(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.402(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.455(7) . ?
C36 C43 1.372(6) . ?
C36 C37 1.456(6) . ?
C37 C42 1.401(6) . ?
C37 C38 1.404(7) . ?
C38 C39 1.380(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.398(7) . ?
C39 H39 0.9500 . ?
C40 C41 1.365(7) . ?
C40 H40 0.9500 . ?
C41 C42 1.385(6) . ?
C41 H41 0.9500 . ?
C43 C44 1.409(7) . ?
C44 C45 1.400(6) . ?
C45 C52 1.366(7) . ?
C46 C47 1.357(8) . ?
C46 C51 1.387(7) . ?
C47 C48 1.374(9) . ?
C47 H47 0.9500 . ?
C48 C49 1.373(8) . ?
C48 H48 0.9500 . ?
C49 C50 1.439(8) . ?
C49 H49 0.9500 . ?
C50 C51 1.412(7) . ?
C50 H50 0.9500 . ?
C51 C52 1.442(6) . ?

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
C25 O1 C26 104.8(3) . . ?
C28 O2 C29 105.2(4) . . ?
C42 O3 C43 104.9(3) . . ?
C45 O4 C46 106.0(4) . . ?
C6 C1 C2 118.3(4) . . ?
C6 C1 C18 119.2(4) . . ?
C2 C1 C18 121.7(4) . . ?
C3 C2 C1 122.1(4) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 119.5(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.7(5) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 118.5(4) . . ?
C1 C6 C7 119.5(4) . . ?
C5 C6 C7 121.5(4) . . ?
C8 C7 C6 118.9(4) . . ?
C8 C7 C36 117.6(4) . . ?
C6 C7 C36 123.2(4) . . ?
C9 C8 C7 121.6(4) . . ?
C9 C8 C17 119.3(4) . . ?
C7 C8 C17 119.0(4) . . ?
C8 C9 C44 120.0(4) . . ?
C8 C9 C10 121.9(4) . . ?
C44 C9 C10 118.1(4) . . ?
C11 C10 C15 119.6(4) . . ?
C11 C10 C9 122.0(4) . . ?
C15 C10 C9 118.4(4) . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 C52 118.2(4) . . ?
C12 C11 C52 121.9(5) . . ?
C13 C12 C11 119.8(5) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 122.6(5) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
C13 C14 C15 119.8(5) . . ?
C13 C14 C35 123.2(5) . . ?
C15 C14 C35 116.9(4) . . ?
C16 C15 C14 122.3(4) . . ?
C16 C15 C10 119.5(4) . . ?
C14 C15 C10 118.1(4) . . ?
C15 C16 C17 122.0(4) . . ?
C15 C16 C27 119.0(4) . . ?
C17 C16 C27 119.0(4) . . ?
C18 C17 C16 122.3(4) . . ?
C18 C17 C8 119.5(4) . . ?
C16 C17 C8 118.3(4) . . ?
C17 C18 C19 117.8(4) . . ?
C17 C18 C1 118.7(4) . . ?
C19 C18 C1 123.2(4) . . ?
C26 C19 C18 117.6(4) . . ?
C26 C19 C20 105.3(4) . . ?
C18 C19 C20 137.1(4) . . ?
C21 C20 C25 116.6(4) . . ?
C21 C20 C19 138.5(4) . . ?
C25 C20 C19 104.8(4) . . ?
C20 C21 C22 119.2(5) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C23 C22 C21 121.7(5) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C24 C23 C22 120.5(5) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 117.3(5) . . ?
C23 C24 H24 121.3 . . ?
C25 C24 H24 121.3 . . ?
C24 C25 O1 123.0(4) . . ?
C24 C25 C20 124.6(4) . . ?
O1 C25 C20 112.4(4) . . ?
O1 C26 C27 121.4(4) . . ?
O1 C26 C19 112.7(4) . . ?
C27 C26 C19 125.9(4) . . ?
C26 C27 C28 127.1(4) . . ?
C26 C27 C16 116.4(4) . . ?
C28 C27 C16 116.4(4) . . ?
C35 C28 O2 112.0(4) . . ?
C35 C28 C27 125.6(4) . . ?
O2 C28 C27 122.4(4) . . ?
C30 C29 C34 126.2(5) . . ?
C30 C29 O2 123.2(5) . . ?
C34 C29 O2 110.6(4) . . ?
C29 C30 C31 113.9(6) . . ?
C29 C30 H30 123.1 . . ?
C31 C30 H30 123.1 . . ?
C32 C31 C30 123.6(6) . . ?
C32 C31 H31 118.2 . . ?
C30 C31 H31 118.2 . . ?
C31 C32 C33 119.8(5) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C34 C33 C32 119.7(5) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C34 C29 116.8(5) . . ?
C33 C34 C35 138.5(5) . . ?
C29 C34 C35 104.6(4) . . ?
C28 C35 C14 119.6(4) . . ?
C28 C35 C34 107.5(4) . . ?
C14 C35 C34 132.8(5) . . ?
C43 C36 C7 118.5(4) . . ?
C43 C36 C37 105.1(4) . . ?
C7 C36 C37 136.3(4) . . ?
C42 C37 C38 117.0(4) . . ?
C42 C37 C36 105.2(4) . . ?
C38 C37 C36 137.6(4) . . ?
C39 C38 C37 119.0(4) . . ?
C39 C38 H38 120.5 . . ?
C37 C38 H38 120.5 . . ?
C38 C39 C40 121.9(5) . . ?
C38 C39 H39 119.1 . . ?
C40 C39 H39 119.1 . . ?
C41 C40 C39 120.4(5) . . ?
C41 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
C40 C41 C42 117.4(4) . . ?
C40 C41 H41 121.3 . . ?
C42 C41 H41 121.3 . . ?
O3 C42 C41 124.0(4) . . ?
O3 C42 C37 111.9(4) . . ?
C41 C42 C37 124.1(5) . . ?
C36 C43 O3 112.9(4) . . ?
C36 C43 C44 125.3(4) . . ?
O3 C43 C44 121.7(4) . . ?
C45 C44 C43 127.0(4) . . ?
C45 C44 C9 117.1(4) . . ?
C43 C44 C9 115.8(4) . . ?
O4 C45 C52 111.0(4) . . ?
O4 C45 C44 123.7(5) . . ?
C52 C45 C44 125.3(5) . . ?
C47 C46 C51 125.4(6) . . ?
C47 C46 O4 123.8(6) . . ?
C51 C46 O4 110.8(5) . . ?
C46 C47 C48 115.5(6) . . ?
C46 C47 H47 122.3 . . ?
C48 C47 H47 122.3 . . ?
C49 C48 C47 124.6(6) . . ?
C49 C48 H48 117.7 . . ?
C47 C48 H48 117.7 . . ?
C48 C49 C50 118.5(6) . . ?
C48 C49 H49 120.8 . . ?
C50 C49 H49 120.8 . . ?
C51 C50 C49 117.8(6) . . ?
C51 C50 H50 121.1 . . ?
C49 C50 H50 121.1 . . ?
C46 C51 C50 118.2(5) . . ?
C46 C51 C52 104.2(4) . . ?
C50 C51 C52 137.5(5) . . ?
C45 C52 C11 119.2(4) . . ?
C45 C52 C51 107.9(4) . . ?
C11 C52 C51 132.8(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
C6 C1 C2 C3 3.9(7) . . . . ?
C18 C1 C2 C3 173.8(4) . . . . ?
C1 C2 C3 C4 -3.8(8) . . . . ?
C2 C3 C4 C5 1.1(8) . . . . ?
C3 C4 C5 C6 1.4(8) . . . . ?
C2 C1 C6 C5 -1.4(6) . . . . ?
C18 C1 C6 C5 -171.6(4) . . . . ?
C2 C1 C6 C7 170.2(4) . . . . ?
C18 C1 C6 C7 0.0(6) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
C4 C5 C6 C7 -172.6(5) . . . . ?
C1 C6 C7 C8 -19.1(6) . . . . ?
C5 C6 C7 C8 152.2(4) . . . . ?
C1 C6 C7 C36 168.0(4) . . . . ?
C5 C6 C7 C36 -20.7(7) . . . . ?
C6 C7 C8 C9 -162.3(4) . . . . ?
C36 C7 C8 C9 11.0(6) . . . . ?
C6 C7 C8 C17 20.4(6) . . . . ?
C36 C7 C8 C17 -166.3(4) . . . . ?
C7 C8 C9 C44 -2.3(6) . . . . ?
C17 C8 C9 C44 175.0(4) . . . . ?
C7 C8 C9 C10 176.3(4) . . . . ?
C17 C8 C9 C10 -6.4(6) . . . . ?
C8 C9 C10 C11 -174.7(4) . . . . ?
C44 C9 C10 C11 3.9(6) . . . . ?
C8 C9 C10 C15 7.5(6) . . . . ?
C44 C9 C10 C15 -174.0(4) . . . . ?
C15 C10 C11 C12 -3.3(6) . . . . ?
C9 C10 C11 C12 178.9(4) . . . . ?
C15 C10 C11 C52 175.6(4) . . . . ?
C9 C10 C11 C52 -2.3(6) . . . . ?
C10 C11 C12 C13 4.7(7) . . . . ?
C52 C11 C12 C13 -174.1(4) . . . . ?
C11 C12 C13 C14 -2.3(7) . . . . ?
C12 C13 C14 C15 -1.5(7) . . . . ?
C12 C13 C14 C35 176.7(4) . . . . ?
C13 C14 C15 C16 -177.6(4) . . . . ?
C35 C14 C15 C16 4.1(6) . . . . ?
C13 C14 C15 C10 2.8(6) . . . . ?
C35 C14 C15 C10 -175.5(4) . . . . ?
C11 C10 C15 C16 -180.0(4) . . . . ?
C9 C10 C15 C16 -2.1(6) . . . . ?
C11 C10 C15 C14 -0.4(6) . . . . ?
C9 C10 C15 C14 177.5(4) . . . . ?
C14 C15 C16 C17 176.3(4) . . . . ?
C10 C15 C16 C17 -4.2(6) . . . . ?
C14 C15 C16 C27 -3.1(6) . . . . ?
C10 C15 C16 C27 176.4(4) . . . . ?
C15 C16 C17 C18 -174.8(4) . . . . ?
C27 C16 C17 C18 4.6(6) . . . . ?
C15 C16 C17 C8 5.2(6) . . . . ?
C27 C16 C17 C8 -175.4(4) . . . . ?
C9 C8 C17 C18 -179.9(4) . . . . ?
C7 C8 C17 C18 -2.5(6) . . . . ?
C9 C8 C17 C16 0.1(6) . . . . ?
C7 C8 C17 C16 177.5(4) . . . . ?
C16 C17 C18 C19 -11.0(6) . . . . ?
C8 C17 C18 C19 169.0(4) . . . . ?
C16 C17 C18 C1 163.6(4) . . . . ?
C8 C17 C18 C1 -16.5(6) . . . . ?
C6 C1 C18 C17 17.8(6) . . . . ?
C2 C1 C18 C17 -152.0(4) . . . . ?
C6 C1 C18 C19 -168.0(4) . . . . ?
C2 C1 C18 C19 22.2(6) . . . . ?
C17 C18 C19 C26 10.6(6) . . . . ?
C1 C18 C19 C26 -163.7(4) . . . . ?
C17 C18 C19 C20 -172.4(5) . . . . ?
C1 C18 C19 C20 13.4(8) . . . . ?
C26 C19 C20 C21 -175.2(5) . . . . ?
C18 C19 C20 C21 7.5(9) . . . . ?
C26 C19 C20 C25 1.8(4) . . . . ?
C18 C19 C20 C25 -175.5(5) . . . . ?
C25 C20 C21 C22 2.4(6) . . . . ?
C19 C20 C21 C22 179.1(5) . . . . ?
C20 C21 C22 C23 -0.3(7) . . . . ?
C21 C22 C23 C24 -1.6(7) . . . . ?
C22 C23 C24 C25 1.2(7) . . . . ?
C23 C24 C25 O1 -177.2(4) . . . . ?
C23 C24 C25 C20 1.1(7) . . . . ?
C26 O1 C25 C24 -179.8(4) . . . . ?
C26 O1 C25 C20 1.7(5) . . . . ?
C21 C20 C25 C24 -2.9(7) . . . . ?
C19 C20 C25 C24 179.3(4) . . . . ?
C21 C20 C25 O1 175.5(4) . . . . ?
C19 C20 C25 O1 -2.2(5) . . . . ?
C25 O1 C26 C27 -179.2(4) . . . . ?
C25 O1 C26 C19 -0.5(5) . . . . ?
C18 C19 C26 O1 177.1(3) . . . . ?
C20 C19 C26 O1 -0.9(5) . . . . ?
C18 C19 C26 C27 -4.3(6) . . . . ?
C20 C19 C26 C27 177.8(4) . . . . ?
O1 C26 C27 C28 -2.7(7) . . . . ?
C19 C26 C27 C28 178.7(4) . . . . ?
O1 C26 C27 C16 176.4(4) . . . . ?
C19 C26 C27 C16 -2.1(6) . . . . ?
C15 C16 C27 C26 -178.5(4) . . . . ?
C17 C16 C27 C26 2.1(6) . . . . ?
C15 C16 C27 C28 0.7(6) . . . . ?
C17 C16 C27 C28 -178.7(4) . . . . ?
C29 O2 C28 C35 -1.3(5) . . . . ?
C29 O2 C28 C27 176.9(4) . . . . ?
C26 C27 C28 C35 179.7(4) . . . . ?
C16 C27 C28 C35 0.6(6) . . . . ?
C26 C27 C28 O2 1.7(7) . . . . ?
C16 C27 C28 O2 -177.4(4) . . . . ?
C28 O2 C29 C30 -177.6(4) . . . . ?
C28 O2 C29 C34 1.9(5) . . . . ?
C34 C29 C30 C31 -1.2(7) . . . . ?
O2 C29 C30 C31 178.2(5) . . . . ?
C29 C30 C31 C32 1.8(8) . . . . ?
C30 C31 C32 C33 -1.9(9) . . . . ?
C31 C32 C33 C34 1.3(8) . . . . ?
C32 C33 C34 C29 -0.7(7) . . . . ?
C32 C33 C34 C35 -176.4(5) . . . . ?
C30 C29 C34 C33 0.7(7) . . . . ?
O2 C29 C34 C33 -178.7(4) . . . . ?
C30 C29 C34 C35 177.8(5) . . . . ?
O2 C29 C34 C35 -1.7(5) . . . . ?
O2 C28 C35 C14 178.6(4) . . . . ?
C27 C28 C35 C14 0.5(7) . . . . ?
O2 C28 C35 C34 0.3(5) . . . . ?
C27 C28 C35 C34 -177.8(4) . . . . ?
C13 C14 C35 C28 179.1(4) . . . . ?
C15 C14 C35 C28 -2.7(6) . . . . ?
C13 C14 C35 C34 -3.2(8) . . . . ?
C15 C14 C35 C34 175.0(4) . . . . ?
C33 C34 C35 C28 176.9(6) . . . . ?
C29 C34 C35 C28 0.8(5) . . . . ?
C33 C34 C35 C14 -1.1(9) . . . . ?
C29 C34 C35 C14 -177.2(5) . . . . ?
C8 C7 C36 C43 -11.3(6) . . . . ?
C6 C7 C36 C43 161.6(4) . . . . ?
C8 C7 C36 C37 164.0(5) . . . . ?
C6 C7 C36 C37 -23.1(8) . . . . ?
C43 C36 C37 C42 -2.9(5) . . . . ?
C7 C36 C37 C42 -178.7(5) . . . . ?
C43 C36 C37 C38 172.8(5) . . . . ?
C7 C36 C37 C38 -3.(1) . . . . ?
C42 C37 C38 C39 -2.2(7) . . . . ?
C36 C37 C38 C39 -177.6(5) . . . . ?
C37 C38 C39 C40 0.0(7) . . . . ?
C38 C39 C40 C41 1.5(8) . . . . ?
C39 C40 C41 C42 -0.6(8) . . . . ?
C43 O3 C42 C41 -178.1(5) . . . . ?
C43 O3 C42 C37 0.0(5) . . . . ?
C40 C41 C42 O3 176.1(5) . . . . ?
C40 C41 C42 C37 -1.8(8) . . . . ?
C38 C37 C42 O3 -174.9(4) . . . . ?
C36 C37 C42 O3 1.8(5) . . . . ?
C38 C37 C42 C41 3.2(7) . . . . ?
C36 C37 C42 C41 180.0(5) . . . . ?
C7 C36 C43 O3 179.9(4) . . . . ?
C37 C36 C43 O3 3.2(5) . . . . ?
C7 C36 C43 C44 3.1(7) . . . . ?
C37 C36 C43 C44 -173.6(4) . . . . ?
C42 O3 C43 C36 -2.1(5) . . . . ?
C42 O3 C43 C44 174.8(4) . . . . ?
C36 C43 C44 C45 -177.6(5) . . . . ?
O3 C43 C44 C45 5.9(7) . . . . ?
C36 C43 C44 C9 5.6(7) . . . . ?
O3 C43 C44 C9 -170.8(4) . . . . ?
C8 C9 C44 C45 176.9(4) . . . . ?
C10 C9 C44 C45 -1.7(6) . . . . ?
C8 C9 C44 C43 -6.0(6) . . . . ?
C10 C9 C44 C43 175.4(4) . . . . ?
C46 O4 C45 C52 0.9(6) . . . . ?
C46 O4 C45 C44 -178.1(5) . . . . ?
C43 C44 C45 O4 -0.1(8) . . . . ?
C9 C44 C45 O4 176.7(4) . . . . ?
C43 C44 C45 C52 -178.9(5) . . . . ?
C9 C44 C45 C52 -2.1(7) . . . . ?
C45 O4 C46 C47 178.3(6) . . . . ?
C45 O4 C46 C51 -2.7(6) . . . . ?
C51 C46 C47 C48 -0.3(9) . . . . ?
O4 C46 C47 C48 178.6(6) . . . . ?
C46 C47 C48 C49 0.8(10) . . . . ?
C47 C48 C49 C50 -0.8(10) . . . . ?
C48 C49 C50 C51 0.3(8) . . . . ?
C47 C46 C51 C50 -0.2(9) . . . . ?
O4 C46 C51 C50 -179.2(5) . . . . ?
C47 C46 C51 C52 -177.7(6) . . . . ?
O4 C46 C51 C52 3.3(6) . . . . ?
C49 C50 C51 C46 0.1(8) . . . . ?
C49 C50 C51 C52 176.6(6) . . . . ?
O4 C45 C52 C11 -175.1(4) . . . . ?
C44 C45 C52 C11 3.8(7) . . . . ?
O4 C45 C52 C51 1.1(6) . . . . ?
C44 C45 C52 C51 -179.9(5) . . . . ?
C10 C11 C52 C45 -1.5(7) . . . . ?
C12 C11 C52 C45 177.3(4) . . . . ?
C10 C11 C52 C51 -176.6(5) . . . . ?
C12 C11 C52 C51 2.2(8) . . . . ?
C46 C51 C52 C45 -2.7(5) . . . . ?
C50 C51 C52 C45 -179.4(6) . . . . ?
C46 C51 C52 C11 172.9(5) . . . . ?
C50 C51 C52 C11 -3.9(10) . . . . ?

_refine_diff_density_max         1.015
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.078


_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_m19033
_database_code_depnum_ccdc_archive 'CCDC 2040903'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;University of Kentucky
United States of America
;
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2017). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2021-01-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_STRVA01_m19033              
;
PROBLEM: Flack parameter is too small
RESPONSE: Can't tell if this is twinned by inversion due to lack of any usable anomalous signal. Should be of no consequence though as the molecule is achiral and the space group has a mirror and a glide.
;
# Added during the CSD deposition process: Tuesday 27 October 2020 05:06 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3

_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        'contorted pentabenzocoronene'
_chemical_name_common            cPBC
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H22'
_chemical_formula_sum            'C44 H22'
_chemical_formula_weight         550.61

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           46
_space_group_name_H-M_alt        'I m a 2'
_space_group_name_Hall           'I 2 -2a'

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

_cell_length_a                   26.178(2)
_cell_length_b                   7.8792(10)
_cell_length_c                   12.5967(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2598.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    2295
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      26.35

_exptl_crystal_description       flake
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            11400
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.700
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_point_group_measured_fraction_full 0.904

_reflns_number_total             2723
_reflns_number_gt                1706
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_max     0.769
_reflns_Friedel_fraction_full    0.799
_reflns_special_details          
; 
Reflections were merged by SHELXL according to the crystal 
class for the calculation of statistics and refinement. 
 
_reflns_Friedel_fraction is defined as the number of unique 
Friedel pairs measured divided by the number that would be 
possible theoretically, ignoring centric projections and 
systematic absences. 
;

_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0244P)²+1.4584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
Flack 'x' determined using 512 quotients [(I+)-(I-)]/[(I+)+(I-)] 
[Parsons, Flack and Wagner (2013)]. 
;
_refine_ls_abs_structure_Flack   -10.(1)
# Can't tell if this is twinned by inversion due to lack of any usable
# anomalous signal. Should be of no consequence though as the molecule
# is achiral and the space group has a mirror and a glide.
_chemical_absolute_configuration .
_refine_ls_number_reflns         2723
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.025
_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
C1 C 0.72398(16) 0.3248(6) 0.8722(4) 0.0324(12) Uani 1 1 d . . . . .
H1 H 0.706247 0.298252 0.935858 0.039 Uiso 1 1 calc R U . . .
C2 C 0.6959(2) 0.3632(6) 0.7798(4) 0.0297(12) Uani 1 1 d . . . . .
C3 C 0.72288(15) 0.4236(6) 0.6907(4) 0.027(1) Uani 1 1 d . . . . .
C4 C 0.69513(12) 0.4895(7) 0.6004(4) 0.0263(8) Uani 1 1 d . . . . .
C5 C 0.72270(16) 0.5498(6) 0.5092(4) 0.0273(11) Uani 1 1 d . . . . .
C6 C 0.69588(19) 0.6093(6) 0.4210(4) 0.0276(11) Uani 1 1 d . . . . .
C7 C 0.72324(17) 0.6146(6) 0.3209(4) 0.0328(11) Uani 1 1 d . . . . .
C8 C 0.69708(15) 0.5937(5) 0.2217(3) 0.033(1) Uani 1 1 d . . . . .
H8 H 0.660797 0.591331 0.220813 0.040 Uiso 1 1 calc R U . . .
C9 C 0.72351(15) 0.5770(5) 0.1280(3) 0.0348(10) Uani 1 1 d . . . . .
H9 H 0.705430 0.565350 0.063022 0.042 Uiso 1 1 calc R U . . .
C10 C 0.64147(19) 0.3305(6) 0.7701(4) 0.0263(11) Uani 1 1 d . . . . .
C11 C 0.61539(16) 0.2307(6) 0.8438(4) 0.0285(11) Uani 1 1 d . . . . .
H11 H 0.632322 0.197376 0.907182 0.034 Uiso 1 1 calc R U . . .
C12 C 0.56622(18) 0.1795(6) 0.8273(4) 0.0322(11) Uani 1 1 d . . . . .
H12 H 0.549291 0.112004 0.878971 0.039 Uiso 1 1 calc R U . . .
C13 C 0.54106(16) 0.2263(6) 0.7352(4) 0.0321(12) Uani 1 1 d . . . . .
H13 H 0.507503 0.185781 0.721728 0.038 Uiso 1 1 calc R U . . .
C14 C 0.56472(18) 0.3318(7) 0.6629(4) 0.0297(12) Uani 1 1 d . . . . .
H14 H 0.546772 0.365903 0.600919 0.036 Uiso 1 1 calc R U . . .
C15 C 0.61497(17) 0.3897(6) 0.6793(4) 0.0261(11) Uani 1 1 d . . . . .
C16 C 0.64160(12) 0.4940(7) 0.6016(5) 0.0278(8) Uani 1 1 d . . . . .
C17 C 0.61621(18) 0.6034(6) 0.5268(4) 0.0275(11) Uani 1 1 d . . . . .
C18 C 0.56727(19) 0.6709(6) 0.5463(4) 0.0292(12) Uani 1 1 d . . . . .
H18 H 0.549229 0.635751 0.607930 0.035 Uiso 1 1 calc R U . . .
C19 C 0.54493(17) 0.7855(6) 0.4792(4) 0.0327(12) Uani 1 1 d . . . . .
H19 H 0.512041 0.829939 0.494756 0.039 Uiso 1 1 calc R U . . .
C20 C 0.57085(19) 0.8368(6) 0.3872(4) 0.0337(12) Uani 1 1 d . . . . .
H20 H 0.555102 0.914086 0.339451 0.040 Uiso 1 1 calc R U . . .
C21 C 0.61893(17) 0.7759(6) 0.3659(4) 0.0317(12) Uani 1 1 d . . . . .
H21 H 0.636179 0.812541 0.303597 0.038 Uiso 1 1 calc R U . . .
C22 C 0.64337(18) 0.6590(6) 0.4352(4) 0.0285(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.362(8) 4_655 ?
C1 C2 1.410(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.410(6) . ?
C2 C10 1.452(7) . ?
C3 C3 1.420(8) 4_655 ?
C3 C4 1.446(6) . ?
C4 C16 1.402(4) . ?
C4 C5 1.437(7) . ?
C5 C6 1.395(7) . ?
C5 C5 1.429(8) 4_655 ?
C6 C22 1.440(6) . ?
C6 C7 1.451(7) . ?
C7 C7 1.401(9) 4_655 ?
C7 C8 1.434(7) . ?
C8 C9 1.375(6) . ?
C8 H8 0.9500 . ?
C9 C9 1.387(8) 4_655 ?
C9 H9 0.9500 . ?
C10 C11 1.396(6) . ?
C10 C15 1.416(6) . ?
C11 C12 1.365(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.408(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.456(7) . ?
C16 C17 1.440(7) . ?
C17 C18 1.408(6) . ?
C17 C22 1.424(6) . ?
C18 C19 1.368(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.402(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.422(6) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1 C2 121.5(3) 4_655 . ?
C1 C1 H1 119.3 4_655 . ?
C2 C1 H1 119.3 . . ?
C1 C2 C3 117.9(4) . . ?
C1 C2 C10 122.9(4) . . ?
C3 C2 C10 119.0(4) . . ?
C2 C3 C3 120.1(3) . 4_655 ?
C2 C3 C4 119.7(4) . . ?
C3 C3 C4 120.2(2) 4_655 . ?
C16 C4 C5 120.2(5) . . ?
C16 C4 C3 120.1(5) . . ?
C5 C4 C3 119.7(3) . . ?
C6 C5 C5 120.2(3) . 4_655 ?
C6 C5 C4 119.6(4) . . ?
C5 C5 C4 120.2(2) 4_655 . ?
C5 C6 C22 118.2(4) . . ?
C5 C6 C7 117.0(4) . . ?
C22 C6 C7 124.8(4) . . ?
C7 C7 C8 118.5(3) 4_655 . ?
C7 C7 C6 119.6(3) 4_655 . ?
C8 C7 C6 121.2(4) . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C9 120.2(2) . 4_655 ?
C8 C9 H9 119.9 . . ?
C9 C9 H9 119.9 4_655 . ?
C11 C10 C15 118.9(4) . . ?
C11 C10 C2 121.6(4) . . ?
C15 C10 C2 119.3(4) . . ?
C12 C11 C10 121.8(5) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 119.8(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.2(5) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 118.0(5) . . ?
C14 C15 C16 122.1(4) . . ?
C10 C15 C16 119.6(4) . . ?
C4 C16 C17 118.0(5) . . ?
C4 C16 C15 118.2(5) . . ?
C17 C16 C15 123.8(3) . . ?
C18 C17 C22 118.6(5) . . ?
C18 C17 C16 122.1(4) . . ?
C22 C17 C16 118.9(4) . . ?
C19 C18 C17 122.0(5) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.3(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 121.2(5) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C17 118.2(4) . . ?
C21 C22 C6 122.0(4) . . ?
C17 C22 C6 119.6(4) . . ?

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
C1 C1 C2 C3 -8.2(5) 4_655 . . . ?
C1 C1 C2 C10 166.7(3) 4_655 . . . ?
C1 C2 C3 C3 8.1(5) . . . 4_655 ?
C10 C2 C3 C3 -167.0(3) . . . 4_655 ?
C1 C2 C3 C4 -170.4(4) . . . . ?
C10 C2 C3 C4 14.5(7) . . . . ?
C2 C3 C4 C16 0.3(8) . . . . ?
C3 C3 C4 C16 -178.2(4) 4_655 . . . ?
C2 C3 C4 C5 -179.6(4) . . . . ?
C3 C3 C4 C5 2.0(6) 4_655 . . . ?
C16 C4 C5 C6 -1.5(8) . . . . ?
C3 C4 C5 C6 178.4(4) . . . . ?
C16 C4 C5 C5 178.2(4) . . . 4_655 ?
C3 C4 C5 C5 -2.0(6) . . . 4_655 ?
C5 C5 C6 C22 -160.2(3) 4_655 . . . ?
C4 C5 C6 C22 19.5(7) . . . . ?
C5 C5 C6 C7 20.4(5) 4_655 . . . ?
C4 C5 C6 C7 -159.9(4) . . . . ?
C5 C6 C7 C7 -20.3(5) . . . 4_655 ?
C22 C6 C7 C7 160.4(4) . . . 4_655 ?
C5 C6 C7 C8 150.0(5) . . . . ?
C22 C6 C7 C8 -29.3(7) . . . . ?
C7 C7 C8 C9 -1.2(5) 4_655 . . . ?
C6 C7 C8 C9 -171.6(4) . . . . ?
C7 C8 C9 C9 1.2(5) . . . 4_655 ?
C1 C2 C10 C11 -12.0(7) . . . . ?
C3 C2 C10 C11 162.8(4) . . . . ?
C1 C2 C10 C15 173.1(5) . . . . ?
C3 C2 C10 C15 -12.1(7) . . . . ?
C15 C10 C11 C12 4.4(7) . . . . ?
C2 C10 C11 C12 -170.5(5) . . . . ?
C10 C11 C12 C13 0.3(7) . . . . ?
C11 C12 C13 C14 -3.4(8) . . . . ?
C12 C13 C14 C15 1.9(8) . . . . ?
C13 C14 C15 C10 2.7(7) . . . . ?
C13 C14 C15 C16 176.8(5) . . . . ?
C11 C10 C15 C14 -5.8(6) . . . . ?
C2 C10 C15 C14 169.3(4) . . . . ?
C11 C10 C15 C16 -180.0(4) . . . . ?
C2 C10 C15 C16 -5.0(7) . . . . ?
C5 C4 C16 C17 -18.2(8) . . . . ?
C3 C4 C16 C17 161.9(5) . . . . ?
C5 C4 C16 C15 162.6(5) . . . . ?
C3 C4 C16 C15 -17.2(8) . . . . ?
C14 C15 C16 C4 -154.4(5) . . . . ?
C10 C15 C16 C4 19.6(8) . . . . ?
C14 C15 C16 C17 26.5(8) . . . . ?
C10 C15 C16 C17 -159.5(4) . . . . ?
C4 C16 C17 C18 -153.8(5) . . . . ?
C15 C16 C17 C18 25.3(8) . . . . ?
C4 C16 C17 C22 19.8(7) . . . . ?
C15 C16 C17 C22 -161.1(4) . . . . ?
C22 C17 C18 C19 1.1(7) . . . . ?
C16 C17 C18 C19 174.7(5) . . . . ?
C17 C18 C19 C20 0.8(8) . . . . ?
C18 C19 C20 C21 -1.6(8) . . . . ?
C19 C20 C21 C22 0.6(7) . . . . ?
C20 C21 C22 C17 1.3(7) . . . . ?
C20 C21 C22 C6 -172.5(5) . . . . ?
C18 C17 C22 C21 -2.1(7) . . . . ?
C16 C17 C22 C21 -175.9(4) . . . . ?
C18 C17 C22 C6 171.9(4) . . . . ?
C16 C17 C22 C6 -1.9(7) . . . . ?
C5 C6 C22 C21 156.0(5) . . . . ?
C7 C6 C22 C21 -24.6(7) . . . . ?
C5 C6 C22 C17 -17.7(7) . . . . ?
C7 C6 C22 C17 161.7(5) . . . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
