# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_BD15m
_database_code_depnum_ccdc_archive 'CCDC 1524575'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H18 O5'
_chemical_formula_sum            'C25 H18 O5'
_chemical_formula_weight         398.39

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.5463(10)
_cell_length_b                   21.489(3)
_cell_length_c                   12.4234(17)
_cell_angle_alpha                90
_cell_angle_beta                 105.179(2)
_cell_angle_gamma                90
_cell_volume                     1944.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9681
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      28.07

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22589
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.945
_diffrn_reflns_theta_max         28.262
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4691
_reflns_number_gt                3919
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0739P)²+0.3350P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4691
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
C1 C 0.66547(17) 0.58770(7) 0.25194(11) 0.0470(3) Uani 1 1 d . . . . .
C2 C 0.60497(17) 0.48806(6) 0.15791(10) 0.0449(3) Uani 1 1 d . . . . .
C3 C 0.6801(2) 0.43797(7) 0.11520(13) 0.0552(3) Uani 1 1 d . . . . .
H3 H 0.8054 0.4365 0.1208 0.066 Uiso 1 1 calc R U . . .
C4 C 0.5669(2) 0.39049(7) 0.06451(14) 0.0595(4) Uani 1 1 d . . . . .
H4 H 0.6166 0.3566 0.0360 0.071 Uiso 1 1 calc R U . . .
C5 C 0.3796(2) 0.39216(7) 0.05512(14) 0.0594(4) Uani 1 1 d . . . . .
H5 H 0.3052 0.3595 0.0210 0.071 Uiso 1 1 calc R U . . .
C6 C 0.3038(2) 0.44216(6) 0.09631(12) 0.0514(3) Uani 1 1 d . . . . .
H6 H 0.1782 0.4435 0.0893 0.062 Uiso 1 1 calc R U . . .
C7 C 0.41631(17) 0.49081(6) 0.14854(10) 0.0426(3) Uani 1 1 d . . . . .
C8 C 0.36978(16) 0.64308(6) 0.28036(10) 0.0393(3) Uani 1 1 d . . . . .
H8 H 0.3925 0.6824 0.2463 0.047 Uiso 1 1 calc R U . . .
C9 C 0.35724(16) 0.54611(6) 0.19289(10) 0.0402(3) Uani 1 1 d . . . . .
C10 C 0.16849(16) 0.62073(5) 0.22433(10) 0.0398(3) Uani 1 1 d . . . . .
H10 H 0.0930 0.6235 0.2775 0.048 Uiso 1 1 calc R U . . .
C11 C 0.47317(16) 0.59166(6) 0.24146(10) 0.0411(3) Uani 1 1 d . . . . .
C12 C 0.08438(16) 0.65955(6) 0.12091(10) 0.0406(3) Uani 1 1 d . . . . .
C13 C 0.03489(16) 0.72454(6) 0.13814(9) 0.0400(3) Uani 1 1 d . . . . .
C14 C -0.0060(2) 0.76483(6) 0.04758(11) 0.0501(3) Uani 1 1 d . . . . .
H14 H -0.0094 0.7495 -0.0229 0.060 Uiso 1 1 calc R U . . .
C15 C -0.0416(2) 0.82687(7) 0.05941(11) 0.0528(3) Uani 1 1 d . . . . .
H15 H -0.0680 0.8531 -0.0022 0.063 Uiso 1 1 calc R U . . .
C16 C -0.03778(18) 0.84974(6) 0.16416(11) 0.0474(3) Uani 1 1 d . . . . .
C17 C -0.0025(2) 0.81014(7) 0.25529(11) 0.0530(3) Uani 1 1 d . . . . .
H17 H -0.0034 0.8254 0.3252 0.064 Uiso 1 1 calc R U . . .
C18 C 0.0338(2) 0.74838(6) 0.24252(10) 0.0479(3) Uani 1 1 d . . . . .
H18 H 0.0580 0.7221 0.3041 0.057 Uiso 1 1 calc R U . . .
C19 C -0.0792(3) 0.95423(8) 0.10008(17) 0.0774(5) Uani 1 1 d . . . . .
H19A H 0.0243 0.9498 0.0694 0.116 Uiso 1 1 calc R U . . .
H19B H -0.0802 0.9955 0.1297 0.116 Uiso 1 1 calc R U . . .
H19C H -0.1904 0.9474 0.0426 0.116 Uiso 1 1 calc R U . . .
C20 C 0.41357(17) 0.65107(7) 0.40588(10) 0.0462(3) Uani 1 1 d . . . . .
C21 C 0.4647(2) 0.70850(8) 0.45375(14) 0.0652(4) Uani 1 1 d . . . . .
H21 H 0.4734 0.7422 0.4086 0.078 Uiso 1 1 calc R U . . .
C22 C 0.5030(3) 0.71658(12) 0.56807(16) 0.0902(7) Uani 1 1 d . . . . .
H22 H 0.5382 0.7555 0.5990 0.108 Uiso 1 1 calc R U . . .
C23 C 0.4897(3) 0.66846(16) 0.63459(16) 0.0993(8) Uani 1 1 d . . . . .
H23 H 0.5151 0.6742 0.7113 0.119 Uiso 1 1 calc R U . . .
C24 C 0.4389(3) 0.61107(15) 0.58959(18) 0.0998(8) Uani 1 1 d . . . . .
H24 H 0.4285 0.5780 0.6359 0.120 Uiso 1 1 calc R U . . .
C25 C 0.4021(3) 0.60152(10) 0.47396(14) 0.0723(5) Uani 1 1 d . . . . .
H25 H 0.3704 0.5622 0.4438 0.087 Uiso 1 1 calc R U . . .
O1 O 0.72378(12) 0.53427(5) 0.20881(8) 0.0524(3) Uani 1 1 d . . . . .
O2 O 0.78183(14) 0.62522(6) 0.29475(10) 0.0673(3) Uani 1 1 d . . . . .
O3 O 0.18045(11) 0.55653(4) 0.18966(8) 0.0458(2) Uani 1 1 d . . . . .
O4 O 0.07019(15) 0.63784(5) 0.02888(8) 0.0580(3) Uani 1 1 d . . . . .
O5 O -0.06659(17) 0.91023(5) 0.18624(9) 0.0640(3) Uani 1 1 d . . . . .


_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
C1 O2 1.2081(17) . ?
C1 O1 1.3864(17) . ?
C1 C11 1.4252(17) . ?
C2 O1 1.3758(16) . ?
C2 C3 1.3855(19) . ?
C2 C7 1.3991(17) . ?
C3 C4 1.373(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.3949(19) . ?
C6 H6 0.9300 . ?
C7 C9 1.4293(17) . ?
C8 C11 1.5035(17) . ?
C8 C20 1.5167(17) . ?
C8 C10 1.5712(16) . ?
C8 H8 0.9800 . ?
C9 O3 1.3430(14) . ?
C9 C11 1.3458(17) . ?
C10 O3 1.4551(15) . ?
C10 C12 1.5240(17) . ?
C10 H10 0.9800 . ?
C12 O4 1.2134(15) . ?
C12 C13 1.4756(17) . ?
C13 C14 1.3887(17) . ?
C13 C18 1.3963(17) . ?
C14 C15 1.375(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.3842(19) . ?
C15 H15 0.9300 . ?
C16 O5 1.3576(16) . ?
C16 C17 1.3853(19) . ?
C17 C18 1.3728(19) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O5 1.413(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C25 1.377(2) . ?
C20 C21 1.380(2) . ?
C21 C22 1.384(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.344(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.367(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.405(3) . ?
C24 H24 0.9300 . ?
C25 H25 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
O2 C1 O1 117.08(12) . . ?
O2 C1 C11 127.28(13) . . ?
O1 C1 C11 115.64(11) . . ?
O1 C2 C3 117.00(12) . . ?
O1 C2 C7 122.29(11) . . ?
C3 C2 C7 120.71(13) . . ?
C4 C3 C2 119.00(13) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 121.13(14) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 120.12(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 119.75(13) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 119.27(12) . . ?
C6 C7 C9 126.10(12) . . ?
C2 C7 C9 114.60(11) . . ?
C11 C8 C20 114.96(10) . . ?
C11 C8 C10 98.96(9) . . ?
C20 C8 C10 114.53(10) . . ?
C11 C8 H8 109.3 . . ?
C20 C8 H8 109.3 . . ?
C10 C8 H8 109.3 . . ?
O3 C9 C11 114.60(11) . . ?
O3 C9 C7 122.32(11) . . ?
C11 C9 C7 123.08(11) . . ?
O3 C10 C12 108.30(10) . . ?
O3 C10 C8 107.06(9) . . ?
C12 C10 C8 110.31(10) . . ?
O3 C10 H10 110.4 . . ?
C12 C10 H10 110.4 . . ?
C8 C10 H10 110.4 . . ?
C9 C11 C1 121.62(12) . . ?
C9 C11 C8 110.34(10) . . ?
C1 C11 C8 128.04(11) . . ?
O4 C12 C13 122.50(12) . . ?
O4 C12 C10 119.89(11) . . ?
C13 C12 C10 117.47(10) . . ?
C14 C13 C18 118.01(12) . . ?
C14 C13 C12 118.92(11) . . ?
C18 C13 C12 123.03(11) . . ?
C15 C14 C13 121.73(12) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 119.21(12) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
O5 C16 C15 124.39(12) . . ?
O5 C16 C17 115.45(12) . . ?
C15 C16 C17 120.17(12) . . ?
C18 C17 C16 120.06(12) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.78(12) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.83(15) . . ?
C25 C20 C8 120.81(13) . . ?
C21 C20 C8 120.36(13) . . ?
C20 C21 C22 120.93(19) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.06(18) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 119.2(2) . . ?
C20 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C2 O1 C1 122.74(10) . . ?
C9 O3 C10 106.69(9) . . ?
C16 O5 C19 118.06(13) . . ?

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
O1 C2 C3 C4 179.45(13) . . . . ?
C7 C2 C3 C4 -0.8(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C5 C6 C7 C2 0.2(2) . . . . ?
C5 C6 C7 C9 178.48(13) . . . . ?
O1 C2 C7 C6 -179.71(12) . . . . ?
C3 C2 C7 C6 0.51(19) . . . . ?
O1 C2 C7 C9 1.83(18) . . . . ?
C3 C2 C7 C9 -177.94(12) . . . . ?
C6 C7 C9 O3 1.0(2) . . . . ?
C2 C7 C9 O3 179.30(11) . . . . ?
C6 C7 C9 C11 -179.34(13) . . . . ?
C2 C7 C9 C11 -1.01(18) . . . . ?
C11 C8 C10 O3 14.27(11) . . . . ?
C20 C8 C10 O3 -108.52(12) . . . . ?
C11 C8 C10 C12 -103.35(11) . . . . ?
C20 C8 C10 C12 133.86(11) . . . . ?
O3 C9 C11 C1 179.77(11) . . . . ?
C7 C9 C11 C1 0.06(19) . . . . ?
O3 C9 C11 C8 0.26(15) . . . . ?
C7 C9 C11 C8 -179.45(11) . . . . ?
O2 C1 C11 C9 -179.17(14) . . . . ?
O1 C1 C11 C9 0.14(18) . . . . ?
O2 C1 C11 C8 0.3(2) . . . . ?
O1 C1 C11 C8 179.56(11) . . . . ?
C20 C8 C11 C9 113.42(12) . . . . ?
C10 C8 C11 C9 -9.07(12) . . . . ?
C20 C8 C11 C1 -66.06(17) . . . . ?
C10 C8 C11 C1 171.46(12) . . . . ?
O3 C10 C12 O4 -12.72(15) . . . . ?
C8 C10 C12 O4 104.14(13) . . . . ?
O3 C10 C12 C13 171.47(10) . . . . ?
C8 C10 C12 C13 -71.68(13) . . . . ?
O4 C12 C13 C14 -8.83(19) . . . . ?
C10 C12 C13 C14 166.87(12) . . . . ?
O4 C12 C13 C18 173.69(13) . . . . ?
C10 C12 C13 C18 -10.62(18) . . . . ?
C18 C13 C14 C15 1.8(2) . . . . ?
C12 C13 C14 C15 -175.78(13) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 O5 178.45(14) . . . . ?
C14 C15 C16 C17 -1.4(2) . . . . ?
O5 C16 C17 C18 -178.11(13) . . . . ?
C15 C16 C17 C18 1.8(2) . . . . ?
C16 C17 C18 C13 -0.3(2) . . . . ?
C14 C13 C18 C17 -1.5(2) . . . . ?
C12 C13 C18 C17 176.04(13) . . . . ?
C11 C8 C20 C25 -53.27(17) . . . . ?
C10 C8 C20 C25 60.39(17) . . . . ?
C11 C8 C20 C21 127.15(14) . . . . ?
C10 C8 C20 C21 -119.19(14) . . . . ?
C25 C20 C21 C22 -0.3(2) . . . . ?
C8 C20 C21 C22 179.28(15) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C21 C20 C25 C24 1.3(3) . . . . ?
C8 C20 C25 C24 -178.29(16) . . . . ?
C23 C24 C25 C20 -1.5(3) . . . . ?
C3 C2 O1 C1 178.01(12) . . . . ?
C7 C2 O1 C1 -1.77(19) . . . . ?
O2 C1 O1 C2 -179.92(13) . . . . ?
C11 C1 O1 C2 0.70(18) . . . . ?
C11 C9 O3 C10 9.70(14) . . . . ?
C7 C9 O3 C10 -170.59(11) . . . . ?
C12 C10 O3 C9 103.83(11) . . . . ?
C8 C10 O3 C9 -15.10(12) . . . . ?
C15 C16 O5 C19 -8.1(2) . . . . ?
C17 C16 O5 C19 171.83(15) . . . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042

