# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1454862'
_audit_update_record             
;
2016-02-20 deposited with the CCDC.
2016-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 O3'
_chemical_formula_weight         328.35

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   11.353(7)
_cell_length_b                   16.909(12)
_cell_length_c                   8.235(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1580.8(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5690
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      28.03

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_T_max  0.8645
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10295
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         28.19
_reflns_number_total             3614
_reflns_number_gt                3351
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0363P)²+0.2053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(9)
_refine_ls_number_reflns         3614
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.04132(9) 0.69142(6) 1.24397(15) 0.0505(3) Uani 1 1 d . . .
O2 O 0.14716(9) 0.71417(5) 1.20386(14) 0.0437(2) Uani 1 1 d . . .
O3 O 0.33492(9) 0.67195(6) 1.24572(13) 0.0450(2) Uani 1 1 d . . .
H3 H 0.3697 0.7145 1.2433 0.068 Uiso 1 1 calc R . .
C6 C -0.00894(10) 0.53207(7) 1.10393(15) 0.0322(2) Uani 1 1 d . . .
C10 C 0.19778(10) 0.59032(7) 1.10509(16) 0.0311(2) Uani 1 1 d . . .
C11 C 0.27309(10) 0.52634(7) 1.04667(17) 0.0332(3) Uani 1 1 d . . .
C17 C 0.27741(12) 0.71186(7) 0.97771(18) 0.0373(3) Uani 1 1 d . . .
C8 C 0.05191(11) 0.66874(7) 1.19708(18) 0.0377(3) Uani 1 1 d . . .
C16 C 0.38295(11) 0.51406(8) 1.1137(2) 0.0455(3) Uani 1 1 d . . .
H16 H 0.4094 0.5463 1.1976 0.055 Uiso 1 1 calc R . .
C9 C 0.24567(11) 0.67273(7) 1.13540(18) 0.0365(3) Uani 1 1 d . . .
C7 C 0.08254(10) 0.59124(7) 1.12984(16) 0.0320(2) Uani 1 1 d . . .
C2 C -0.19983(13) 0.50086(11) 1.0055(2) 0.0520(4) Uani 1 1 d . . .
H2 H -0.2698 0.5168 0.9568 0.062 Uiso 1 1 calc R . .
C1 C -0.11329(11) 0.55493(9) 1.03402(18) 0.0413(3) Uani 1 1 d . . .
H1 H -0.1250 0.6076 1.0060 0.050 Uiso 1 1 calc R . .
C12 C 0.23645(13) 0.47712(8) 0.92480(17) 0.0409(3) Uani 1 1 d . . .
H12 H 0.1627 0.4847 0.8781 0.049 Uiso 1 1 calc R . .
C20 C 0.33307(16) 0.77533(10) 0.6797(2) 0.0560(4) Uani 1 1 d . . .
H20 H 0.3511 0.7960 0.5781 0.067 Uiso 1 1 calc R . .
C18 C 0.20656(13) 0.76740(9) 0.9068(2) 0.0521(4) Uani 1 1 d . . .
H18 H 0.1384 0.7839 0.9596 0.062 Uiso 1 1 calc R . .
C14 C 0.41554(15) 0.40597(10) 0.9365(2) 0.0562(4) Uani 1 1 d . . .
H14 H 0.4639 0.3654 0.8991 0.067 Uiso 1 1 calc R . .
C21 C 0.40480(16) 0.72119(10) 0.7500(2) 0.0588(4) Uani 1 1 d . . .
H21 H 0.4729 0.7052 0.6967 0.071 Uiso 1 1 calc R . .
C15 C 0.45317(12) 0.45417(10) 1.0564(3) 0.0575(5) Uani 1 1 d . . .
H15 H 0.5277 0.4467 1.1008 0.069 Uiso 1 1 calc R . .
C19 C 0.23503(16) 0.79886(11) 0.7593(2) 0.0615(5) Uani 1 1 d . . .
H19 H 0.1864 0.8370 0.7130 0.074 Uiso 1 1 calc R . .
C5 C 0.00566(11) 0.45386(8) 1.14657(17) 0.0389(3) Uani 1 1 d . . .
H5 H 0.0756 0.4373 1.1944 0.047 Uiso 1 1 calc R . .
C4 C -0.08274(14) 0.40051(9) 1.1186(2) 0.0505(4) Uani 1 1 d . . .
H4 H -0.0727 0.3479 1.1486 0.061 Uiso 1 1 calc R . .
C22 C 0.37812(13) 0.68986(9) 0.8984(2) 0.0506(4) Uani 1 1 d . . .
H22 H 0.4288 0.6533 0.9458 0.061 Uiso 1 1 calc R . .
C13 C 0.30708(15) 0.41667(9) 0.8704(2) 0.0528(4) Uani 1 1 d . . .
H13 H 0.2807 0.3832 0.7885 0.063 Uiso 1 1 calc R . .
C3 C -0.18485(13) 0.42372(11) 1.0475(2) 0.0549(4) Uani 1 1 d . . .
H3A H -0.2442 0.3871 1.0276 0.066 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
O1 C8 1.1902(18) . ?
O2 C8 1.3277(17) . ?
O2 C9 1.4351(17) . ?
O3 C9 1.3610(17) . ?
O3 H3 0.8200 . ?
C6 C1 1.3728(19) . ?
C6 C5 1.3782(19) . ?
C6 C7 1.4578(18) . ?
C10 C7 1.3242(19) . ?
C10 C11 1.4604(18) . ?
C10 C9 1.5164(18) . ?
C11 C12 1.369(2) . ?
C11 C16 1.3796(19) . ?
C17 C18 1.367(2) . ?
C17 C22 1.368(2) . ?
C17 C9 1.501(2) . ?
C8 C7 1.4645(19) . ?
C16 C15 1.372(2) . ?
C16 H16 0.9300 . ?
C2 C3 1.360(3) . ?
C2 C1 1.363(2) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C12 C13 1.374(2) . ?
C12 H12 0.9300 . ?
C20 C19 1.352(3) . ?
C20 C21 1.355(3) . ?
C20 H20 0.9300 . ?
C18 C19 1.365(3) . ?
C18 H18 0.9300 . ?
C14 C15 1.350(3) . ?
C14 C13 1.358(3) . ?
C14 H14 0.9300 . ?
C21 C22 1.365(3) . ?
C21 H21 0.9300 . ?
C15 H15 0.9300 . ?
C19 H19 0.9300 . ?
C5 C4 1.369(2) . ?
C5 H5 0.9300 . ?
C4 C3 1.357(3) . ?
C4 H4 0.9300 . ?
C22 H22 0.9300 . ?
C13 H13 0.9300 . ?
C3 H3A 0.9300 . ?

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
C8 O2 C9 109.62(11) . . ?
C9 O3 H3 109.5 . . ?
C1 C6 C5 118.74(12) . . ?
C1 C6 C7 118.88(12) . . ?
C5 C6 C7 122.38(11) . . ?
C7 C10 C11 129.63(11) . . ?
C7 C10 C9 108.55(11) . . ?
C11 C10 C9 121.67(11) . . ?
C12 C11 C16 118.46(13) . . ?
C12 C11 C10 120.94(12) . . ?
C16 C11 C10 120.60(13) . . ?
C18 C17 C22 118.32(15) . . ?
C18 C17 C9 122.05(14) . . ?
C22 C17 C9 119.59(12) . . ?
O1 C8 O2 121.62(13) . . ?
O1 C8 C7 128.48(12) . . ?
O2 C8 C7 109.89(11) . . ?
C15 C16 C11 119.91(16) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
O3 C9 O2 108.83(12) . . ?
O3 C9 C17 113.76(11) . . ?
O2 C9 C17 108.16(11) . . ?
O3 C9 C10 111.59(11) . . ?
O2 C9 C10 103.53(10) . . ?
C17 C9 C10 110.40(12) . . ?
C10 C7 C6 132.32(12) . . ?
C10 C7 C8 107.66(11) . . ?
C6 C7 C8 120.02(11) . . ?
C3 C2 C1 120.63(15) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C1 C6 120.38(15) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C11 C12 C13 120.94(14) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C19 C20 C21 119.11(17) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C19 C18 C17 120.55(17) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C15 C14 C13 119.96(14) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C20 C21 C22 120.74(17) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C14 C15 C16 120.88(15) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C20 C19 C18 120.79(16) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C4 C5 C6 120.08(13) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C3 C4 C5 120.55(15) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C21 C22 C17 120.46(15) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
C14 C13 C12 119.83(17) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C4 C3 C2 119.61(14) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?

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
C7 C10 C11 C12 39.7(2) . . . . ?
C9 C10 C11 C12 -135.27(14) . . . . ?
C7 C10 C11 C16 -140.12(15) . . . . ?
C9 C10 C11 C16 44.91(19) . . . . ?
C9 O2 C8 O1 -178.41(13) . . . . ?
C9 O2 C8 C7 2.84(16) . . . . ?
C12 C11 C16 C15 0.8(2) . . . . ?
C10 C11 C16 C15 -179.35(13) . . . . ?
C8 O2 C9 O3 -125.72(12) . . . . ?
C8 O2 C9 C17 110.23(12) . . . . ?
C8 O2 C9 C10 -6.92(15) . . . . ?
C18 C17 C9 O3 -131.67(14) . . . . ?
C22 C17 C9 O3 50.62(18) . . . . ?
C18 C17 C9 O2 -10.64(17) . . . . ?
C22 C17 C9 O2 171.65(13) . . . . ?
C18 C17 C9 C10 101.98(15) . . . . ?
C22 C17 C9 C10 -75.73(16) . . . . ?
C7 C10 C9 O3 125.82(13) . . . . ?
C11 C10 C9 O3 -58.26(18) . . . . ?
C7 C10 C9 O2 8.94(15) . . . . ?
C11 C10 C9 O2 -175.14(12) . . . . ?
C7 C10 C9 C17 -106.62(13) . . . . ?
C11 C10 C9 C17 69.30(15) . . . . ?
C11 C10 C7 C6 -2.3(2) . . . . ?
C9 C10 C7 C6 173.17(14) . . . . ?
C11 C10 C7 C8 177.08(13) . . . . ?
C9 C10 C7 C8 -7.43(15) . . . . ?
C1 C6 C7 C10 -136.07(15) . . . . ?
C5 C6 C7 C10 43.7(2) . . . . ?
C1 C6 C7 C8 44.59(19) . . . . ?
C5 C6 C7 C8 -135.64(13) . . . . ?
O1 C8 C7 C10 -175.49(15) . . . . ?
O2 C8 C7 C10 3.16(15) . . . . ?
O1 C8 C7 C6 4.0(2) . . . . ?
O2 C8 C7 C6 -177.35(12) . . . . ?
C3 C2 C1 C6 0.8(2) . . . . ?
C5 C6 C1 C2 -0.9(2) . . . . ?
C7 C6 C1 C2 178.84(14) . . . . ?
C16 C11 C12 C13 0.2(2) . . . . ?
C10 C11 C12 C13 -179.67(13) . . . . ?
C22 C17 C18 C19 1.1(2) . . . . ?
C9 C17 C18 C19 -176.62(15) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C11 C16 C15 C14 -1.1(2) . . . . ?
C21 C20 C19 C18 -1.6(3) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C1 C6 C5 C4 0.2(2) . . . . ?
C7 C6 C5 C4 -179.54(14) . . . . ?
C6 C5 C4 C3 0.6(2) . . . . ?
C20 C21 C22 C17 0.9(3) . . . . ?
C18 C17 C22 C21 -1.9(2) . . . . ?
C9 C17 C22 C21 175.94(14) . . . . ?
C15 C14 C13 C12 0.7(2) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
C5 C4 C3 C2 -0.8(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        28.19
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.032
