# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_CPDBC-1
_database_code_depnum_ccdc_archive 'CCDC 2027309'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C54 H32 O8'
_chemical_formula_moiety         'C54 H32 O8'
_chemical_formula_weight         808.80
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n n n'
_space_group_name_Hall           '-P 2ab 2bc'
_space_group_IT_number           48
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2+Z
3 1/2+X,-Y,1/2+Z
4 1/2+X,1/2+Y,-Z
5 -X,-Y,-Z
6 +X,-1/2-Y,-1/2-Z
7 -1/2-X,+Y,-1/2-Z
8 -1/2-X,-1/2-Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   3.7618(5)
_cell_length_b                   24.323(3)
_cell_length_c                   41.416(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3789.5(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13822
_cell_measurement_theta_min      0.58
_cell_measurement_theta_max      16.23
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    0.709
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864.00
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.331
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.42860
_diffrn_measurement_device_type  'SPring-8 BL02B1, PILATUS 3XCdTe 1M'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            51032
_diffrn_reflns_av_unetI/netI     0.1003
_diffrn_reflns_av_R_equivalents  0.2226
_diffrn_reflns_theta_max         16.160
_diffrn_reflns_theta_min         0.585
_diffrn_reflns_theta_full        14.902
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       53
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4341
_reflns_number_gt                2658
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2556
_refine_ls_wR_factor_gt          0.2390
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4341
_refine_ls_number_parameters     142
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1439P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.0302(5) 0.56204(8) 0.51822(3) 0.0774(5) Uani 1 1 d . . . . .
O2 O 0.7757(5) 0.48424(8) 0.53614(4) 0.0829(6) Uani 1 1 d . . . . .
H2 H 0.854619 0.472076 0.518561 0.099 Uiso 1 1 calc R U . . .
C1 C 0.250000 0.72095(12) 0.750000 0.0469(6) Uani 1 2 d S T P . .
C2 C 0.3232(5) 0.69246(9) 0.71961(4) 0.0480(5) Uani 1 1 d . . . . .
C3 C 0.3069(5) 0.72163(8) 0.68985(4) 0.0473(5) Uani 1 1 d . . . . .
C4 C 0.4057(5) 0.69405(9) 0.66109(4) 0.0525(5) Uani 1 1 d . . . . .
H4 H 0.395179 0.713736 0.641304 0.063 Uiso 1 1 calc R U . . .
C5 C 0.5163(5) 0.63999(9) 0.66044(4) 0.0507(5) Uani 1 1 d . . . . .
C6 C 0.5401(5) 0.61217(9) 0.69002(4) 0.0529(5) Uani 1 1 d . . . . .
H6 H 0.618355 0.575039 0.690389 0.063 Uiso 1 1 calc R U . . .
C7 C 0.4522(5) 0.63778(9) 0.71844(4) 0.0522(5) Uani 1 1 d . . . . .
H7 H 0.478782 0.618078 0.738101 0.063 Uiso 1 1 calc R U . . .
C8 C 0.6096(5) 0.61254(9) 0.62942(4) 0.0547(5) Uani 1 1 d . . . . .
C9 C 0.7668(6) 0.64248(10) 0.60417(4) 0.0587(6) Uani 1 1 d . . . . .
H9 H 0.819486 0.680370 0.607026 0.070 Uiso 1 1 calc R U . . .
C10 C 0.8456(6) 0.61690(10) 0.57500(4) 0.0622(6) Uani 1 1 d . . . . .
H10 H 0.948483 0.637520 0.557912 0.075 Uiso 1 1 calc R U . . .
C11 C 0.7745(6) 0.56129(10) 0.57075(5) 0.0615(6) Uani 1 1 d . . . . .
C12 C 0.6199(6) 0.53135(10) 0.59544(5) 0.0632(6) Uani 1 1 d . . . . .
H12 H 0.567138 0.493489 0.592471 0.076 Uiso 1 1 calc R U . . .
C13 C 0.5417(6) 0.55707(10) 0.62474(5) 0.0589(6) Uani 1 1 d . . . . .
H13 H 0.440128 0.536176 0.641788 0.071 Uiso 1 1 calc R U . . .
C14 C 0.8685(6) 0.53461(12) 0.53946(5) 0.0661(6) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C14 1.260(3) . ?
O2 C14 1.281(3) . ?
O2 H2 0.8400 . ?
C1 C1 1.413(6) 6_577 ?
C1 C2 1.463(2) 7_657 ?
C1 C2 1.463(2) . ?
C2 C7 1.416(3) . ?
C2 C3 1.424(2) . ?
C3 C4 1.416(2) . ?
C3 C3 1.445(4) 8_675 ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(3) . ?
C5 C8 1.490(2) . ?
C6 C7 1.372(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.387(3) . ?
C8 C9 1.405(3) . ?
C9 C10 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 C14 1.492(3) . ?
C12 C13 1.397(3) . ?
C12 H12 0.9500 . ?
C13 H13 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
C14 O2 H2 109.5 . . ?
C1 C1 C2 118.28(13) 6_577 7_657 ?
C1 C1 C2 118.28(13) 6_577 . ?
C2 C1 C2 123.4(3) 7_657 . ?
C7 C2 C3 116.94(16) . . ?
C7 C2 C1 122.59(17) . . ?
C3 C2 C1 120.05(19) . . ?
C4 C3 C2 118.73(19) . . ?
C4 C3 C3 122.01(12) . 8_675 ?
C2 C3 C3 119.26(12) . 8_675 ?
C5 C4 C3 123.17(17) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C4 C5 C6 117.51(17) . . ?
C4 C5 C8 121.02(17) . . ?
C6 C5 C8 121.5(2) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 122.56(17) . . ?
C6 C7 H7 118.7 . . ?
C2 C7 H7 118.7 . . ?
C13 C8 C9 118.55(17) . . ?
C13 C8 C5 120.87(18) . . ?
C9 C8 C5 120.6(2) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.95(18) . . ?
C12 C11 C14 120.8(2) . . ?
C10 C11 C14 119.2(2) . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 121.2(2) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
O1 C14 O2 124.25(19) . . ?
O1 C14 C11 119.4(2) . . ?
O2 C14 C11 116.4(2) . . ?

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 C7 157.14(15) 6_577 . . . ?
C2 C1 C2 C7 -22.86(15) 7_657 . . . ?
C1 C1 C2 C3 -15.20(19) 6_577 . . . ?
C2 C1 C2 C3 164.80(19) 7_657 . . . ?
C7 C2 C3 C4 2.4(3) . . . . ?
C1 C2 C3 C4 175.19(15) . . . . ?
C7 C2 C3 C3 -177.2(2) . . . 8_675 ?
C1 C2 C3 C3 -4.4(3) . . . 8_675 ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C3 C4 C5 179.8(2) 8_675 . . . ?
C3 C4 C5 C6 -1.9(3) . . . . ?
C3 C4 C5 C8 178.63(18) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C8 C5 C6 C7 -179.73(19) . . . . ?
C5 C6 C7 C2 2.0(3) . . . . ?
C3 C2 C7 C6 -3.6(3) . . . . ?
C1 C2 C7 C6 -176.15(17) . . . . ?
C4 C5 C8 C13 -146.0(2) . . . . ?
C6 C5 C8 C13 34.5(3) . . . . ?
C4 C5 C8 C9 33.6(3) . . . . ?
C6 C5 C8 C9 -145.9(2) . . . . ?
C13 C8 C9 C10 1.2(3) . . . . ?
C5 C8 C9 C10 -178.49(19) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C9 C10 C11 C14 -178.8(2) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C14 C11 C12 C13 178.6(2) . . . . ?
C9 C8 C13 C12 -1.3(3) . . . . ?
C5 C8 C13 C12 178.32(19) . . . . ?
C11 C12 C13 C8 1.3(3) . . . . ?
C12 C11 C14 O1 -175.3(2) . . . . ?
C10 C11 C14 O1 4.3(3) . . . . ?
C12 C11 C14 O2 4.7(3) . . . . ?
C10 C11 C14 O2 -175.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1O O2 . . 5_766 2.620(2) 0.840 1.801 164.6 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"4,4',4'',4'''-(dibenzo[g,p]chrysene-2,7,10,15-tetrayl)tetrabenzoic acid"
_chemical_name_common            CPDBC
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 5-tert-butyl-m-xylen and N,N-dimethylformamide'
####################################################################### 
# 
# 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_CPDBC-2
_database_code_depnum_ccdc_archive 'CCDC 2027310'
loop_
_audit_author_name
_audit_author_address
'Ichiro Hisaki'
;Osaka University
Japan
;
_audit_update_record             
;
2020-09-04 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;

#==============================================================================



# start Validation Reply Form
_vrf_PLAT707_CPDBC               
;
PROBLEM: D...A Calc 45.260(2), Rep 2.451(2), Dev.. 21404.50 Sigma
RESPONSE: Due to disorder of the carboxy group.
;
_vrf_PLAT420_CPDBC               
;
PROBLEM: D-H Without Acceptor O1 --H1O . Please Check
RESPONSE: Due to disorder of the carboxy group.
;
# end Validation Reply Form

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C54 H32 O8'
_chemical_formula_moiety         'C54 H32 O8'
_chemical_formula_weight         808.80
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'I 41/a c d'
_space_group_name_Hall           '-I 4bd 2c'
_space_group_IT_number           142
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, z+1/2'
'y+1/4, x+1/4, z+1/4'
'-y+3/4, x+1/4, z+3/4'
'x, -y+1/2, z+1/2'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+3/4'
'-y+3/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'y+3/4, x+3/4, z+3/4'
'-y+5/4, x+3/4, z+5/4'
'x+1/2, -y+1, z+1'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+5/4'
'-y+5/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, -y, -z-1/2'
'-y-1/4, -x-1/4, -z-1/4'
'y-3/4, -x-1/4, -z-3/4'
'-x, y-1/2, -z-1/2'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-3/4'
'y-3/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-y+1/4, -x+1/4, -z+1/4'
'y-1/4, -x+1/4, -z-1/4'
'-x+1/2, y, -z'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z-1/4'
'y-1/4, x+1/4, -z+1/4'
#------------------------------------------------------------------------------
_cell_length_a                   47.5006(10)
_cell_length_b                   47.5006(10)
_cell_length_c                   7.4170(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     16735.0(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12291
_cell_measurement_theta_min      1.94
_cell_measurement_theta_max      31.59
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    0.661
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3456.00
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.447
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.81106
_diffrn_measurement_device_type  'SPring-8 BL40XU, Pilatus100K, DECTRIS'
_diffrn_reflns_number            98361
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.1742
_diffrn_reflns_theta_max         33.422
_diffrn_reflns_theta_min         1.957
_diffrn_reflns_theta_full        29.120
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_h_max       60
_diffrn_reflns_limit_k_min       -60
_diffrn_reflns_limit_k_max       60
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5222
_reflns_number_gt                3367
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0917
_refine_ls_wR_factor_ref         0.2920
_refine_ls_wR_factor_gt          0.2698
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5222
_refine_ls_number_parameters     141
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.29076(4) 0.18464(6) 0.3898(4) 0.1402(11) Uani 1 1 d D . . . .
H1O H 0.273645 0.183292 0.362763 0.168 Uiso 0.5 1 calc DR U P . .
O2 O 0.27369(3) 0.21746(5) 0.5653(2) 0.0936(7) Uani 1 1 d . . . . .
H2O H 0.258362 0.211812 0.522006 0.112 Uiso 0.5 1 calc DR U P . .
C1 C 0.48959(3) 0.26041(3) 0.875000 0.0294(5) Uani 1 2 d S T P . .
C2 C 0.46049(3) 0.25213(3) 0.8366(2) 0.0308(4) Uani 1 1 d . . . . .
C3 C 0.45280(3) 0.22340(3) 0.8440(2) 0.0313(4) Uani 1 1 d . . . . .
C4 C 0.42565(3) 0.21528(3) 0.7899(2) 0.0348(4) Uani 1 1 d . . . . .
H5 H 0.420876 0.195862 0.791392 0.042 Uiso 1 1 calc R U . . .
C5 C 0.40567(3) 0.23454(3) 0.7345(2) 0.0348(4) Uani 1 1 d . . . . .
C6 C 0.41343(3) 0.26299(3) 0.7267(2) 0.0356(4) Uani 1 1 d . . . . .
H7 H 0.400085 0.276615 0.688114 0.043 Uiso 1 1 calc R U . . .
C7 C 0.44009(3) 0.27143(3) 0.7741(2) 0.0335(4) Uani 1 1 d . . . . .
H4 H 0.444941 0.290773 0.764545 0.040 Uiso 1 1 calc R U . . .
C8 C 0.37701(3) 0.22557(4) 0.6778(2) 0.0396(4) Uani 1 1 d . . . . .
C9 C 0.37266(4) 0.20110(4) 0.5781(2) 0.0464(5) Uani 1 1 d . . . . .
H10 H 0.388194 0.189489 0.546827 0.056 Uiso 1 1 calc R U . . .
C10 C 0.34566(4) 0.19364(4) 0.5243(3) 0.0541(5) Uani 1 1 d . . . . .
H15 H 0.342836 0.176904 0.456639 0.065 Uiso 1 1 calc R U . . .
C11 C 0.32275(4) 0.21044(4) 0.5687(3) 0.0548(5) Uani 1 1 d . . . . .
C12 C 0.32682(4) 0.23435(4) 0.6698(3) 0.0536(5) Uani 1 1 d . . . . .
H13 H 0.311133 0.245615 0.703137 0.064 Uiso 1 1 calc R U . . .
C13 C 0.35363(3) 0.24210(4) 0.7232(3) 0.0464(5) Uani 1 1 d . . . . .
H12 H 0.356222 0.258822 0.791525 0.056 Uiso 1 1 calc R U . . .
C14 C 0.29377(5) 0.20282(6) 0.5016(4) 0.0727(7) Uani 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C14 1.206(3) . ?
O1 H1O 0.8400 . ?
O2 C14 1.271(3) . ?
O2 H2O 0.8400 . ?
C1 C1 1.399(4) 6_655 ?
C1 C2 1.4650(17) . ?
C1 C2 1.4652(17) 19_667 ?
C2 C7 1.412(2) . ?
C2 C3 1.414(2) . ?
C3 C4 1.404(2) . ?
C3 C3 1.459(3) 24_657 ?
C4 C5 1.381(2) . ?
C4 H5 0.9500 . ?
C5 C6 1.402(2) . ?
C5 C8 1.487(2) . ?
C6 C7 1.374(2) . ?
C6 H7 0.9500 . ?
C7 H4 0.9500 . ?
C8 C9 1.393(2) . ?
C8 C13 1.401(2) . ?
C9 C10 1.389(2) . ?
C9 H10 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H15 0.9500 . ?
C11 C12 1.375(3) . ?
C11 C14 1.508(3) . ?
C12 C13 1.384(2) . ?
C12 H13 0.9500 . ?
C13 H12 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
C14 O1 H1O 109.5 . . ?
C14 O2 H2O 109.5 . . ?
C1 C1 C2 118.49(9) 6_655 . ?
C1 C1 C2 118.49(9) 6_655 19_667 ?
C2 C1 C2 123.01(18) . 19_667 ?
C7 C2 C3 117.52(13) . . ?
C7 C2 C1 122.45(13) . . ?
C3 C2 C1 119.72(14) . . ?
C4 C3 C2 119.42(14) . . ?
C4 C3 C3 121.47(9) . 24_657 ?
C2 C3 C3 119.11(9) . 24_657 ?
C5 C4 C3 122.30(14) . . ?
C5 C4 H5 118.9 . . ?
C3 C4 H5 118.9 . . ?
C4 C5 C6 118.04(14) . . ?
C4 C5 C8 121.58(14) . . ?
C6 C5 C8 120.33(15) . . ?
C7 C6 C5 120.85(15) . . ?
C7 C6 H7 119.6 . . ?
C5 C6 H7 119.6 . . ?
C6 C7 C2 121.81(14) . . ?
C6 C7 H4 119.1 . . ?
C2 C7 H4 119.1 . . ?
C9 C8 C13 118.54(15) . . ?
C9 C8 C5 121.65(15) . . ?
C13 C8 C5 119.80(15) . . ?
C10 C9 C8 120.13(17) . . ?
C10 C9 H10 119.9 . . ?
C8 C9 H10 119.9 . . ?
C11 C10 C9 120.60(18) . . ?
C11 C10 H15 119.7 . . ?
C9 C10 H15 119.7 . . ?
C12 C11 C10 119.58(17) . . ?
C12 C11 C14 120.44(19) . . ?
C10 C11 C14 119.96(19) . . ?
C11 C12 C13 120.36(17) . . ?
C11 C12 H13 119.8 . . ?
C13 C12 H13 119.8 . . ?
C12 C13 C8 120.76(18) . . ?
C12 C13 H12 119.6 . . ?
C8 C13 H12 119.6 . . ?
O1 C14 O2 124.0(2) . . ?
O1 C14 C11 120.4(2) . . ?
O2 C14 C11 115.5(2) . . ?

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 C7 -158.11(11) 6_655 . . . ?
C2 C1 C2 C7 21.89(11) 19_667 . . . ?
C1 C1 C2 C3 15.28(15) 6_655 . . . ?
C2 C1 C2 C3 -164.72(15) 19_667 . . . ?
C7 C2 C3 C4 0.0(2) . . . . ?
C1 C2 C3 C4 -173.73(12) . . . . ?
C7 C2 C3 C3 179.34(16) . . . 24_657 ?
C1 C2 C3 C3 5.6(2) . . . 24_657 ?
C2 C3 C4 C5 -2.1(2) . . . . ?
C3 C3 C4 C5 178.56(17) 24_657 . . . ?
C3 C4 C5 C6 2.4(2) . . . . ?
C3 C4 C5 C8 -179.93(14) . . . . ?
C4 C5 C6 C7 -0.5(2) . . . . ?
C8 C5 C6 C7 -178.23(14) . . . . ?
C5 C6 C7 C2 -1.6(2) . . . . ?
C3 C2 C7 C6 1.8(2) . . . . ?
C1 C2 C7 C6 175.38(13) . . . . ?
C4 C5 C8 C9 -38.5(2) . . . . ?
C6 C5 C8 C9 139.21(18) . . . . ?
C4 C5 C8 C13 142.24(17) . . . . ?
C6 C5 C8 C13 -40.1(2) . . . . ?
C13 C8 C9 C10 0.6(3) . . . . ?
C5 C8 C9 C10 -178.73(16) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C9 C10 C11 C14 177.0(2) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C14 C11 C12 C13 -176.60(19) . . . . ?
C11 C12 C13 C8 -1.0(3) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
C5 C8 C13 C12 179.13(17) . . . . ?
C12 C11 C14 O1 167.9(3) . . . . ?
C10 C11 C14 O1 -10.4(4) . . . . ?
C12 C11 C14 O2 -9.4(3) . . . . ?
C10 C11 C14 O2 172.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2O O2 . . 29_656 2.451(2) 0.820 1.694 152.5 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
"4,4',4'',4'''-(dibenzo[g,p]chrysene-2,7,10,15-tetrayl)tetrabenzoic acid"
_chemical_name_common            CPDBC
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 3-carene, N,N-dimethylformamide'
