# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 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_I
_database_code_depnum_ccdc_archive 'CCDC 1832271'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H22.20 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         510.76

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.538(2)
_cell_length_b                   9.367(3)
_cell_length_c                   18.374(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.039(4)
_cell_angle_gamma                90
_cell_volume                     1277.5(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1954
_cell_measurement_theta_min      2.4485
_cell_measurement_theta_max      26.3816
_cell_measurement_temperature    90.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      90.0

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6578
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             2616
_reflns_number_gt                1934
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_gt          0.1853
_refine_ls_wR_factor_ref         0.2043
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         2616
_refine_ls_number_parameters     60
_refine_ls_number_restraints     150
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0865P)²+1.9110P] 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          0.011
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.499
_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 0.0033 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'

_computing_data_collection       'Bruker SMART APEXII'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1B 0.2393(18) 0.3231(16) 0.0231(7) 0.033(5) Uani d U P G 0.100(4) A 2
C C5B 0.4144(19) 0.3714(17) 0.0462(8) 0.024(4) Uani d U P G 0.100(4) A 2
C C4B 0.5112(17) 0.3275(19) 0.1139(9) 0.028(3) Uani d U P G 0.100(4) A 2
H H4B 0.6309 0.3605 0.1297 0.033 Uiso calc U P R 0.100(4) A 2
C C3B 0.433(2) 0.2353(19) 0.1584(7) 0.027(3) Uani d U P G 0.100(4) A 2
H H3B 0.4991 0.2053 0.2047 0.032 Uiso calc U P R 0.100(4) A 2
C C2B 0.258(2) 0.1870(17) 0.1353(8) 0.026(2) Uani d U P G 0.100(4) A 2
C C1B 0.1610(16) 0.2309(17) 0.0676(8) 0.025(3) Uani d U P G 0.100(4) A 2
C C6B 0.1493 0.0961 0.1782 0.029 Uani d U P . 0.1004 A 2
C C7B 0.2648 0.0562 0.247 0.05 Uani d U P . 0.1004 A 2
H H7B 0.3856 0.0882 0.2606 0.06 Uiso calc U P R 0.100(4) A 2
C C8B 0.167 -0.0488 0.2986 0.034 Uani d U P . 0.1004 A 2
H H8B 0.2203 -0.0857 0.3455 0.041 Uiso calc U P R 0.100(4) A 2
C C9B -0.1236 -0.0394 0.1998 0.022 Uani d U P . 0.1004 A 2
H H9B -0.2448 -0.0712 0.1875 0.026 Uiso calc U P R 0.100(4) A 2
C C10B -0.0381 0.0588 0.1504 0.043 Uani d U P . 0.1004 A 2
C C11B -0.0177 -0.0768 0.2604 0.017 Uani d U P . 0.1004 A 2
H H11B -0.0771 -0.1412 0.288 0.021 Uiso calc U P R 0.100(4) A 2
C C12B -0.1296 0.1009 0.0844 0.042 Uani d U P . 0.1004 A 2
H H12B -0.2514 0.0749 0.067 0.051 Uiso calc U P R 0.100(4) A 2
C C13B -0.0071 0.206 0.0343 0.054 Uani d U P . 0.1004 A 2
H H13B -0.0557 0.2431 -0.0131 0.065 Uiso calc U P R 0.100(4) A 2
C C1A -0.0795 -0.0767 0.2424 0.031 Uani d . P . 0.8996 A 1
H H1A -0.14 -0.1366 0.2719 0.038 Uiso calc U P R 0.900(4) A 1
C C2A 0.0977 -0.0354 0.2679 0.028 Uani d . P . 0.8996 A 1
H H2A 0.1586 -0.0679 0.3146 0.034 Uiso calc U P R 0.900(4) A 1
C C3A -0.1686 -0.0297 0.1729 0.031 Uani d . P . 0.8996 A 1
H H3A -0.2896 -0.0584 0.1558 0.037 Uiso calc U P R 0.900(4) A 1
C C4A -0.0837 0.0576 0.1291 0.027 Uani d . P . 0.8996 A 1
C C5A 0.0961 0.1033 0.1528 0.019 Uani d . P . 0.8996 A 1
C C6A 0.1874 0.0548 0.2246 0.022 Uani d . P . 0.8996 A 1
C C7A 0.3691 0.0993 0.2502 0.024 Uani d . P . 0.8996 A 1
H H7A 0.4304 0.068 0.297 0.029 Uiso calc U P R 0.900(4) A 1
C C8A 0.4553 0.1863 0.2079 0.021 Uani d . P . 0.8996 A 1
H H8A 0.5759 0.2155 0.2254 0.025 Uiso calc U P R 0.900(4) A 1
C C9A 0.3642 0.2327 0.1379 0.017 Uani d . P . 0.8996 A 1
C C10A 0.1901 0.1918 0.11 0.017 Uani d . P . 0.8996 A 1
C C11A 0.1118 0.2446 0.0362 0.022 Uani d . P . 0.8996 A 1
H H11A -0.006 0.2152 0.0142 0.026 Uiso calc U P R 0.900(4) A 1
C C12A 0.2026 0.3328 -0.0003 0.021 Uani d . P . 0.8996 A 1
H H12A 0.1482 0.3617 -0.0486 0.025 Uiso calc U P R 0.900(4) A 1
C C13A 0.3887 0.3898 0.0308 0.017 Uani d . P . 0.8996 A 1
O O1A 0.467 0.3173 0.1008 0.02 Uani d . P . 0.8996 A 1
C C8 0.5188 0.3523 -0.0203 0.018 Uani d . . . 1.0 . .
C C9 0.6205 0.455 -0.0492 0.018 Uani d . . . 1.0 . .
C C17 0.7367 0.4132 -0.0976 0.023 Uani d . . . 1.0 . .
C C18 0.5347 0.2096 -0.0399 0.026 Uani d . . . 1.0 . .
C C19 0.649 0.1683 -0.0881 0.03 Uani d . . . 1.0 . .
C C20 0.7507 0.2713 -0.1169 0.027 Uani d . . . 1.0 . .
H H10 0.8080(15) 0.4745(12) -0.1141(6) 0.033(8) Uiso d . . . 1.0 . .
H H7 0.464(4) 0.140(3) -0.0197(16) 0.031(8) Uiso d . . . 1.0 . .
H H8 0.651(4) 0.059(4) -0.1010(19) 0.045(9) Uiso d . . . 1.0 . .
H H20 0.838(4) 0.241(3) -0.1502(17) 0.032(8) Uiso d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1B C5B . 1.39 ?
O1B C1B . 1.39 ?
C5B C4B . 1.39 ?
C5B C8 . 1.575(15) ?
C5B C9 3_665 1.649(17) ?
C4B C3B . 1.39 ?
C4B H4B . 0.95 ?
C3B C2B . 1.39 ?
C3B H3B . 0.95 ?
C2B C1B . 1.39 ?
C2B C6B . 1.497(10) ?
C1B C13B . 1.328(11) ?
C6B C7B . 1.4536 ?
C6B C10B . 1.4583 ?
C7B C8B . 1.6294 ?
C7B H7B . 0.95 ?
C8B C11B . 1.4693 ?
C8B H8B . 0.95 ?
C9B C11B . 1.2992 ?
C9B C10B . 1.5135 ?
C9B H9B . 0.95 ?
C10B C12B . 1.3449 ?
C11B H11B . 0.95 ?
C12B C13B . 1.7219 ?
C12B H12B . 0.95 ?
C13B H13B . 0.95 ?
C1A C2A . 1.3912 ?
C1A C3A . 1.4062 ?
C1A H1A . 0.95 ?
C2A C6A . 1.4104 ?
C2A H2A . 0.95 ?
C3A C4A . 1.3815 ?
C3A H3A . 0.95 ?
C4A C5A . 1.415 ?
C5A C10A . 1.4152 ?
C5A C6A . 1.4513 ?
C6A C7A . 1.4304 ?
C7A C8A . 1.3652 ?
C7A H7A . 0.95 ?
C8A C9A . 1.4172 ?
C8A H8A . 0.95 ?
C9A O1A . 1.3697 ?
C9A C10A . 1.3779 ?
C10A C11A . 1.467 ?
C11A C12A . 1.3273 ?
C11A H11A . 0.95 ?
C12A C13A . 1.5165 ?
C12A H12A . 0.95 ?
C13A O1A . 1.4834 ?
C13A C9 3_665 1.4964 ?
C13A C8 . 1.5132 ?
C8 C9 . 1.3924 ?
C8 C18 . 1.3956 ?
C9 C17 . 1.4072 ?
C9 C13A 3_665 1.4963 ?
C9 C5B 3_665 1.65(4) ?
C17 C20 . 1.3841 ?
C17 H10 . 0.877(11) ?
C18 C19 . 1.393 ?
C18 H7 . 0.95(3) ?
C19 C20 . 1.3931 ?
C19 H8 . 1.05(3) ?
C20 H20 . 1.01(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5B O1B C1B . . 120.0 ?
C4B C5B O1B . . 120.0 ?
C4B C5B C8 . . 113.9(9) ?
O1B C5B C8 . . 107.6(9) ?
C4B C5B C9 . 3_665 108.9(8) ?
O1B C5B C9 . 3_665 100.5(9) ?
C8 C5B C9 . 3_665 104.0(6) ?
C5B C4B C3B . . 120.0 ?
C5B C4B H4B . . 120.0 ?
C3B C4B H4B . . 120.0 ?
C2B C3B C4B . . 120.0 ?
C2B C3B H3B . . 120.0 ?
C4B C3B H3B . . 120.0 ?
C1B C2B C3B . . 120.0 ?
C1B C2B C6B . . 112.9(9) ?
C3B C2B C6B . . 126.9(9) ?
C13B C1B C2B . . 132.0(9) ?
C13B C1B O1B . . 107.9(9) ?
C2B C1B O1B . . 120.0 ?
C7B C6B C10B . . 129.8 ?
C7B C6B C2B . . 107.8(6) ?
C10B C6B C2B . . 122.5(6) ?
C6B C7B C8B . . 113.5 ?
C6B C7B H7B . . 123.2 ?
C8B C7B H7B . . 123.2 ?
C11B C8B C7B . . 108.4 ?
C11B C8B H8B . . 125.8 ?
C7B C8B H8B . . 125.8 ?
C11B C9B C10B . . 114.5 ?
C11B C9B H9B . . 122.7 ?
C10B C9B H9B . . 122.7 ?
C12B C10B C6B . . 124.0 ?
C12B C10B C9B . . 120.9 ?
C6B C10B C9B . . 115.0 ?
C9B C11B C8B . . 138.7 ?
C9B C11B H11B . . 110.7 ?
C8B C11B H11B . . 110.7 ?
C10B C12B C13B . . 114.2 ?
C10B C12B H12B . . 122.9 ?
C13B C12B H12B . . 122.9 ?
C1B C13B C12B . . 114.4(6) ?
C1B C13B H13B . . 122.8 ?
C12B C13B H13B . . 122.8 ?
C2A C1A C3A . . 119.8 ?
C2A C1A H1A . . 120.1 ?
C3A C1A H1A . . 120.1 ?
C1A C2A C6A . . 120.2 ?
C1A C2A H2A . . 119.9 ?
C6A C2A H2A . . 119.9 ?
C4A C3A C1A . . 121.2 ?
C4A C3A H3A . . 119.4 ?
C1A C3A H3A . . 119.4 ?
C3A C4A C5A . . 121.0 ?
C4A C5A C10A . . 123.5 ?
C4A C5A C6A . . 117.5 ?
C10A C5A C6A . . 119.0 ?
C2A C6A C7A . . 121.0 ?
C2A C6A C5A . . 120.2 ?
C7A C6A C5A . . 118.8 ?
C8A C7A C6A . . 120.7 ?
C8A C7A H7A . . 119.6 ?
C6A C7A H7A . . 119.6 ?
C7A C8A C9A . . 119.7 ?
C7A C8A H8A . . 120.1 ?
C9A C8A H8A . . 120.1 ?
O1A C9A C10A . . 124.1 ?
O1A C9A C8A . . 113.7 ?
C10A C9A C8A . . 122.2 ?
C9A C10A C5A . . 119.5 ?
C9A C10A C11A . . 117.0 ?
C5A C10A C11A . . 123.5 ?
C12A C11A C10A . . 121.1 ?
C12A C11A H11A . . 119.4 ?
C10A C11A H11A . . 119.4 ?
C11A C12A C13A . . 123.6 ?
C11A C12A H12A . . 118.2 ?
C13A C12A H12A . . 118.2 ?
O1A C13A C9 . 3_665 106.0 ?
O1A C13A C8 . . 103.2 ?
C9 C13A C8 3_665 . 115.2 ?
O1A C13A C12A . . 111.6 ?
C9 C13A C12A 3_665 . 110.6 ?
C8 C13A C12A . . 109.9 ?
C9A O1A C13A . . 121.5 ?
C9 C8 C18 . . 119.0 ?
C9 C8 C13A . . 122.4 ?
C18 C8 C13A . . 118.5 ?
C9 C8 C5B . . 126.9(5) ?
C18 C8 C5B . . 112.7(5) ?
C8 C9 C17 . . 119.6 ?
C8 C9 C13A . 3_665 122.3 ?
C17 C9 C13A . 3_665 118.1 ?
C8 C9 C5B . 3_665 124.5(11) ?
C17 C9 C5B . 3_665 114.6(11) ?
C20 C17 C9 . . 120.8 ?
C20 C17 H10 . . 117.5(7) ?
C9 C17 H10 . . 121.6(7) ?
C19 C18 C8 . . 121.4 ?
C19 C18 H7 . . 120.2(18) ?
C8 C18 H7 . . 118.4(18) ?
C18 C19 C20 . . 119.4 ?
C18 C19 H8 . . 116.5(17) ?
C20 C19 H8 . . 124.1(17) ?
C17 C20 C19 . . 119.8 ?
C17 C20 H20 . . 120.5(17) ?
C19 C20 H20 . . 119.7(17) ?

