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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd16106
_database_code_depnum_ccdc_archive 'CCDC 1557770'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 O3'
_chemical_formula_weight         302.31

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   7.2027(13)
_cell_length_b                   18.296(3)
_cell_length_c                   22.189(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2924.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3226
_cell_measurement_theta_min      4.453
_cell_measurement_theta_max      45.796

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6522
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16358
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.836
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2868
_reflns_number_gt                2198
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+0.4642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0048(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2868
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1256
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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 0.04522(17) 1.01228(6) 0.35947(5) 0.0487(3) Uani 1 1 d . . . . .
O2 O -0.0738(2) 0.83228(7) 0.21855(6) 0.0784(5) Uani 1 1 d . . . . .
O3 O -0.00014(18) 0.78724(6) 0.56870(5) 0.0549(4) Uani 1 1 d . . . . .
C1 C 0.0840(3) 1.12015(11) 0.12927(9) 0.0702(6) Uani 1 1 d . . . . .
H1 H 0.1146 1.1689 0.1225 0.084 Uiso 1 1 calc R U . . .
C2 C 0.0492(3) 1.07598(13) 0.08157(10) 0.0779(7) Uani 1 1 d . . . . .
H2 H 0.0557 1.0946 0.0426 0.093 Uiso 1 1 calc R U . . .
C3 C 0.0040(3) 1.00346(12) 0.09060(9) 0.0697(6) Uani 1 1 d . . . . .
H3 H -0.0219 0.9737 0.0577 0.084 Uiso 1 1 calc R U . . .
C4 C -0.0029(3) 0.97510(10) 0.14713(8) 0.0559(5) Uani 1 1 d . . . . .
H4 H -0.0309 0.9259 0.1523 0.067 Uiso 1 1 calc R U . . .
C5 C 0.0315(2) 1.01893(9) 0.19793(7) 0.0442(4) Uani 1 1 d . . . . .
C6 C 0.0749(3) 1.09389(9) 0.18871(8) 0.0528(4) Uani 1 1 d . . . . .
C7 C 0.1046(3) 1.14116(9) 0.23827(9) 0.0605(5) Uani 1 1 d . . . . .
H7 H 0.1328 1.1900 0.2309 0.073 Uiso 1 1 calc R U . . .
C8 C 0.0934(3) 1.11780(9) 0.29579(8) 0.0566(5) Uani 1 1 d . . . . .
H8 H 0.1108 1.1492 0.3283 0.068 Uiso 1 1 calc R U . . .
C9 C 0.0545(2) 1.04406(8) 0.30370(7) 0.0450(4) Uani 1 1 d . . . . .
C10 C 0.0256(2) 0.99397(8) 0.25890(7) 0.0413(4) Uani 1 1 d . . . . .
C11 C -0.0048(2) 0.92540(8) 0.29012(7) 0.0422(4) Uani 1 1 d . . . . .
C12 C 0.0127(2) 0.94009(8) 0.35027(7) 0.0437(4) Uani 1 1 d . . . . .
C13 C 0.0093(2) 0.89663(8) 0.40549(7) 0.0441(4) Uani 1 1 d . . . . .
C14 C 0.0919(2) 0.82854(9) 0.40977(7) 0.0481(4) Uani 1 1 d . . . . .
H14 H 0.1491 0.8085 0.3760 0.058 Uiso 1 1 calc R U . . .
C15 C 0.0910(3) 0.78990(9) 0.46316(7) 0.0485(4) Uani 1 1 d . . . . .
H15 H 0.1449 0.7438 0.4650 0.058 Uiso 1 1 calc R U . . .
C16 C 0.0099(2) 0.81984(9) 0.51373(7) 0.0433(4) Uani 1 1 d . . . . .
C17 C -0.0714(3) 0.88836(9) 0.51025(7) 0.0493(4) Uani 1 1 d . . . . .
H17 H -0.1265 0.9088 0.5442 0.059 Uiso 1 1 calc R U . . .
C18 C -0.0709(3) 0.92596(8) 0.45716(7) 0.0484(4) Uani 1 1 d . . . . .
H18 H -0.1252 0.9720 0.4555 0.058 Uiso 1 1 calc R U . . .
C19 C -0.0595(3) 0.85352(9) 0.26961(8) 0.0541(5) Uani 1 1 d . . . . .
H19 H -0.0869 0.8196 0.2995 0.065 Uiso 1 1 calc R U . . .
C20 C 0.0787(3) 0.71698(10) 0.57585(8) 0.0624(5) Uani 1 1 d . . . . .
H20A H 0.0181 0.6832 0.5492 0.094 Uiso 1 1 calc R U . . .
H20B H 0.0627 0.7011 0.6168 0.094 Uiso 1 1 calc R U . . .
H20C H 0.2087 0.7189 0.5664 0.094 Uiso 1 1 calc R U . . .


_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 C12 1.3570(18) . ?
O1 C9 1.3689(19) . ?
O2 C19 1.2022(19) . ?
O3 C16 1.3598(18) . ?
O3 C20 1.414(2) . ?
C1 C2 1.355(3) . ?
C1 C6 1.405(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.421(2) . ?
C5 C10 1.429(2) . ?
C6 C7 1.415(3) . ?
C7 C8 1.348(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(2) . ?
C10 C11 1.450(2) . ?
C11 C12 1.367(2) . ?
C11 C19 1.446(2) . ?
C12 C13 1.461(2) . ?
C13 C14 1.384(2) . ?
C13 C18 1.392(2) . ?
C14 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(2) . ?
C17 C18 1.364(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C12 O1 C9 106.61(12) . . ?
C16 O3 C20 118.56(13) . . ?
C2 C1 C6 121.36(19) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C1 C2 C3 120.23(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.08(18) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.29(15) . . ?
C4 C5 C10 124.88(15) . . ?
C6 C5 C10 116.83(15) . . ?
C1 C6 C7 120.88(17) . . ?
C1 C6 C5 118.38(17) . . ?
C7 C6 C5 120.73(15) . . ?
C8 C7 C6 122.20(16) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 116.07(16) . . ?
C7 C8 H8 122.0 . . ?
C9 C8 H8 122.0 . . ?
C10 C9 O1 111.40(13) . . ?
C10 C9 C8 126.13(15) . . ?
O1 C9 C8 122.45(14) . . ?
C9 C10 C5 118.00(14) . . ?
C9 C10 C11 104.81(14) . . ?
C5 C10 C11 137.20(14) . . ?
C12 C11 C19 120.73(14) . . ?
C12 C11 C10 106.40(13) . . ?
C19 C11 C10 132.66(15) . . ?
O1 C12 C11 110.74(13) . . ?
O1 C12 C13 113.97(13) . . ?
C11 C12 C13 135.26(14) . . ?
C14 C13 C18 117.99(15) . . ?
C14 C13 C12 122.71(14) . . ?
C18 C13 C12 119.21(14) . . ?
C15 C14 C13 121.20(15) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 119.84(15) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
O3 C16 C15 125.34(15) . . ?
O3 C16 C17 115.10(14) . . ?
C15 C16 C17 119.56(14) . . ?
C18 C17 C16 120.20(15) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 121.21(15) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
O2 C19 C11 127.87(16) . . ?
O2 C19 H19 116.1 . . ?
C11 C19 H19 116.1 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 -0.2(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C3 C4 C5 C10 179.40(17) . . . . ?
C2 C1 C6 C7 -177.6(2) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C4 C5 C6 C1 -1.0(2) . . . . ?
C10 C5 C6 C1 179.29(16) . . . . ?
C4 C5 C6 C7 177.83(17) . . . . ?
C10 C5 C6 C7 -1.9(2) . . . . ?
C1 C6 C7 C8 178.78(19) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C9 1.2(3) . . . . ?
C12 O1 C9 C10 0.97(18) . . . . ?
C12 O1 C9 C8 -177.52(16) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 O1 177.75(17) . . . . ?
O1 C9 C10 C5 -179.83(13) . . . . ?
C8 C9 C10 C5 -1.4(3) . . . . ?
O1 C9 C10 C11 0.23(18) . . . . ?
C8 C9 C10 C11 178.65(17) . . . . ?
C4 C5 C10 C9 -177.20(16) . . . . ?
C6 C5 C10 C9 2.5(2) . . . . ?
C4 C5 C10 C11 2.7(3) . . . . ?
C6 C5 C10 C11 -177.57(18) . . . . ?
C9 C10 C11 C12 -1.33(17) . . . . ?
C5 C10 C11 C12 178.74(18) . . . . ?
C9 C10 C11 C19 173.30(19) . . . . ?
C5 C10 C11 C19 -6.6(3) . . . . ?
C9 O1 C12 C11 -1.87(18) . . . . ?
C9 O1 C12 C13 176.61(13) . . . . ?
C19 C11 C12 O1 -173.40(15) . . . . ?
C10 C11 C12 O1 2.01(18) . . . . ?
C19 C11 C12 C13 8.6(3) . . . . ?
C10 C11 C12 C13 -176.02(17) . . . . ?
O1 C12 C13 C14 -138.08(16) . . . . ?
C11 C12 C13 C14 39.9(3) . . . . ?
O1 C12 C13 C18 38.3(2) . . . . ?
C11 C12 C13 C18 -143.7(2) . . . . ?
C18 C13 C14 C15 1.6(2) . . . . ?
C12 C13 C14 C15 178.04(16) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C20 O3 C16 C15 0.3(2) . . . . ?
C20 O3 C16 C17 179.63(16) . . . . ?
C14 C15 C16 O3 179.89(15) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
O3 C16 C17 C18 -179.51(15) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C13 0.4(3) . . . . ?
C14 C13 C18 C17 -1.2(3) . . . . ?
C12 C13 C18 C17 -177.72(16) . . . . ?
C12 C11 C19 O2 -177.11(19) . . . . ?
C10 C11 C19 O2 8.9(3) . . . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4

