# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_reece_57bistricyc_aie2_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2246ct
_database_code_depnum_ccdc_archive 'CCDC 1910665'
loop_
_audit_author_name
_audit_author_address
'Reece Crocker'
;University of New South Wales
Australia
;
_audit_update_record             
;
2019-04-17 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;
_audit_creation_date             2019-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        Tetrabenzo[5,7]fulvalene
_chemical_formula_moiety         'C28 H18'
_chemical_formula_sum            'C28 H18'
_chemical_formula_weight         354.42
_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'

_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   7.9396(10)
_cell_length_b                   19.416(2)
_cell_length_c                   11.7318(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1808.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    100.93
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1834 before and 0.0679 after correction. The Ratio of minimum to maximum transmission is 0.9079. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method 'Hot Toluene'
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.069
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            58565
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         3.098
_diffrn_ambient_temperature      100.93
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1803
_reflns_number_total             2140
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.084
_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)+(0.0333P)²+1.0056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0952
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C3(H3), C15(H15), C22(H22), C2(H2), C1(H1), C19(H19), C20(H20),
 C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C5 C 0.7453(2) 0.250000 0.54858(13) 0.0155(3) Uani 1 2 d S T P . .
C16 C 0.6037(2) 0.250000 0.48499(14) 0.0164(3) Uani 1 2 d S T P . .
C4 C 0.83305(14) 0.31321(6) 0.58813(10) 0.0159(2) Uani 1 1 d . . . . .
C14 C 0.82908(14) 0.33017(6) 0.70457(10) 0.0166(2) Uani 1 1 d . . . . .
C13 C 0.75741(14) 0.28459(6) 0.79134(10) 0.0181(2) Uani 1 1 d . . . . .
H13 H 0.705117 0.306343 0.854647 0.022 Uiso 1 1 calc R . . . .
C18 C 0.38118(15) 0.21228(6) 0.36732(10) 0.0187(3) Uani 1 1 d . . . . .
C17 C 0.51113(15) 0.18895(6) 0.43974(9) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.92308(15) 0.35418(6) 0.51139(10) 0.0192(3) Uani 1 1 d . . . . .
H3 H 0.931089 0.340845 0.433671 0.023 Uiso 1 1 calc R . . . .
C15 C 0.90108(16) 0.39313(6) 0.73851(11) 0.0196(3) Uani 1 1 d . . . . .
H15 H 0.891461 0.407481 0.815650 0.024 Uiso 1 1 calc R . . . .
C22 C 0.53260(16) 0.11813(6) 0.45529(10) 0.0195(3) Uani 1 1 d . . . . .
H22 H 0.616707 0.101248 0.505653 0.023 Uiso 1 1 calc R . . . .
C2 C 1.00073(16) 0.41415(6) 0.54807(11) 0.0211(3) Uani 1 1 d . . . . .
H2 H 1.064017 0.441288 0.496049 0.025 Uiso 1 1 calc R . . . .
C1 C 0.98564(16) 0.43448(6) 0.66141(11) 0.0211(3) Uani 1 1 d . . . . .
H1 H 1.033507 0.476824 0.685839 0.025 Uiso 1 1 calc R . . . .
C19 C 0.27843(16) 0.16656(7) 0.30819(10) 0.0225(3) Uani 1 1 d . . . . .
H19 H 0.192068 0.183101 0.259283 0.027 Uiso 1 1 calc R . . . .
C20 C 0.30430(17) 0.09639(7) 0.32190(11) 0.0249(3) Uani 1 1 d . . . . .
H20 H 0.236964 0.064479 0.280781 0.030 Uiso 1 1 calc R . . . .
C21 C 0.42891(16) 0.07255(7) 0.39590(10) 0.0231(3) Uani 1 1 d . . . . .
H21 H 0.443429 0.024368 0.406024 0.028 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
C5 C16 1.350(2) . ?
C5 C4 1.4856(14) 7_565 ?
C5 C4 1.4856(15) . ?
C16 C17 1.4923(15) . ?
C16 C17 1.4923(15) 7_565 ?
C4 C14 1.4055(16) . ?
C4 C3 1.3980(17) . ?
C14 C13 1.4640(16) . ?
C14 C15 1.4070(16) . ?
C13 C13 1.343(2) 7_565 ?
C13 H13 0.9500 . ?
C18 C18 1.465(3) 7_565 ?
C18 C17 1.4112(16) . ?
C18 C19 1.3909(17) . ?
C17 C22 1.3975(17) . ?
C3 H3 0.9500 . ?
C3 C2 1.3860(17) . ?
C15 H15 0.9500 . ?
C15 C1 1.3833(17) . ?
C22 H22 0.9500 . ?
C22 C21 1.3952(17) . ?
C2 H2 0.9500 . ?
C2 C1 1.3922(18) . ?
C1 H1 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.3872(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.3953(19) . ?
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
C16 C5 C4 124.29(7) . 7_565 ?
C16 C5 C4 124.29(7) . . ?
C4 C5 C4 111.42(14) 7_565 . ?
C5 C16 C17 127.37(7) . . ?
C5 C16 C17 127.37(7) . 7_565 ?
C17 C16 C17 105.19(14) . 7_565 ?
C14 C4 C5 119.12(11) . . ?
C3 C4 C5 120.57(11) . . ?
C3 C4 C14 120.27(11) . . ?
C4 C14 C13 122.88(11) . . ?
C4 C14 C15 118.00(11) . . ?
C15 C14 C13 119.10(11) . . ?
C14 C13 H13 116.4 . . ?
C13 C13 C14 127.20(6) 7_565 . ?
C13 C13 H13 116.4 7_565 . ?
C17 C18 C18 108.73(7) . 7_565 ?
C19 C18 C18 129.66(8) . 7_565 ?
C19 C18 C17 121.61(12) . . ?
C18 C17 C16 108.61(11) . . ?
C22 C17 C16 132.46(11) . . ?
C22 C17 C18 118.93(11) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 C4 120.37(11) . . ?
C2 C3 H3 119.8 . . ?
C14 C15 H15 119.5 . . ?
C1 C15 C14 121.09(11) . . ?
C1 C15 H15 119.5 . . ?
C17 C22 H22 120.4 . . ?
C21 C22 C17 119.14(12) . . ?
C21 C22 H22 120.4 . . ?
C3 C2 H2 120.1 . . ?
C3 C2 C1 119.76(11) . . ?
C1 C2 H2 120.1 . . ?
C15 C1 C2 120.12(11) . . ?
C15 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C18 C19 H19 120.6 . . ?
C20 C19 C18 118.83(12) . . ?
C20 C19 H19 120.6 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.20(12) . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 121.24(12) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?

_olex2_submission_original_sample_id GC-049
_olex2_submission_special_instructions 'No special instructions were received'
