# 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_exp_3413
_database_code_depnum_ccdc_archive 'CCDC 1555526'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 O4'
_chemical_formula_weight         281.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9865(17)
_cell_length_b                   8.511(2)
_cell_length_c                   11.9757(18)
_cell_angle_alpha                88.053(17)
_cell_angle_beta                 77.077(18)
_cell_angle_gamma                84.50(2)
_cell_volume                     690.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    608
_cell_measurement_theta_min      3.7950
_cell_measurement_theta_max      63.4710

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             294
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9245
_exptl_absorpt_correction_T_max  0.9612
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3842
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.79
_diffrn_reflns_theta_max         65.00
_reflns_number_total             2291
_reflns_number_gt                1105
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1572P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.1013(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2291
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2777
_refine_ls_wR_factor_gt          0.2063
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.000
_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 0.4674(4) 0.6696(4) 0.7662(3) 0.0872(11) Uani 1 1 d . . .
O2 O 0.7735(4) 0.5650(4) 0.6474(3) 0.0853(11) Uani 1 1 d . . .
O3 O 0.2161(4) 0.2933(4) 0.6451(3) 0.0930(12) Uani 1 1 d . . .
C1 C -0.7891(7) 0.8657(6) 1.2083(4) 0.0833(14) Uani 1 1 d . . .
H1 H -0.9156 0.8801 1.2541 0.100 Uiso 1 1 calc R . .
C2 C -0.6474(7) 0.9578(6) 1.2224(4) 0.0845(14) Uani 1 1 d . . .
H2 H -0.6777 1.0370 1.2768 0.101 Uiso 1 1 calc R . .
C3 C -0.4576(7) 0.9333(5) 1.1553(4) 0.0770(13) Uani 1 1 d . . .
H3 H -0.3613 0.9961 1.1658 0.092 Uiso 1 1 calc R . .
C4 C -0.4094(6) 0.8173(5) 1.0735(3) 0.0647(11) Uani 1 1 d . . .
C5 C -0.5549(6) 0.7284(6) 1.0584(4) 0.0758(13) Uani 1 1 d . . .
H5 H -0.5270 0.6517 1.0021 0.091 Uiso 1 1 calc R . .
C6 C -0.7443(7) 0.7523(6) 1.1267(4) 0.0843(15) Uani 1 1 d . . .
H6 H -0.8413 0.6901 1.1165 0.101 Uiso 1 1 calc R . .
C7 C -0.2067(6) 0.7950(6) 1.0049(4) 0.0710(12) Uani 1 1 d . . .
H7 H -0.1210 0.8650 1.0193 0.085 Uiso 1 1 calc R . .
C8 C -0.1294(6) 0.6886(6) 0.9254(4) 0.0739(13) Uani 1 1 d . . .
H8 H -0.2119 0.6190 0.9067 0.089 Uiso 1 1 calc R . .
C9 C 0.0750(6) 0.6741(6) 0.8660(3) 0.0711(12) Uani 1 1 d . . .
H9 H 0.1540 0.7471 0.8840 0.085 Uiso 1 1 calc R . .
C10 C 0.1614(6) 0.5678(6) 0.7888(4) 0.0736(13) Uani 1 1 d . . .
H10 H 0.0868 0.4949 0.7663 0.088 Uiso 1 1 calc R . .
C11 C 0.3733(6) 0.5626(5) 0.7377(3) 0.0660(12) Uani 1 1 d . . .
C12 C 0.4792(5) 0.4464(5) 0.6574(3) 0.0602(11) Uani 1 1 d . . .
C13 C 0.6840(6) 0.4528(6) 0.6157(4) 0.0677(12) Uani 1 1 d . . .
C14 C 0.7924(6) 0.3406(6) 0.5357(4) 0.0737(13) Uani 1 1 d . . .
H14 H 0.9268 0.3467 0.5075 0.088 Uiso 1 1 calc R . .
C15 C 0.7037(6) 0.2273(6) 0.5008(4) 0.0706(12) Uani 1 1 d . . .
O4 O 0.5067(4) 0.2166(4) 0.5386(3) 0.0764(9) Uani 1 1 d . . .
C16 C 0.3879(6) 0.3216(6) 0.6189(4) 0.0714(12) Uani 1 1 d . . .
C17 C 0.7961(7) 0.1006(6) 0.4194(4) 0.0932(16) Uani 1 1 d . . .
H17A H 0.7822 -0.0001 0.4574 0.140 Uiso 1 1 calc R . .
H17B H 0.9336 0.1144 0.3919 0.140 Uiso 1 1 calc R . .
H17C H 0.7325 0.1053 0.3559 0.140 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0609(19) 0.108(3) 0.091(2) -0.0323(19) -0.0018(16) -0.0242(18)
O2 0.0539(18) 0.109(3) 0.093(2) -0.0224(19) -0.0055(15) -0.0282(17)
O3 0.0463(18) 0.110(3) 0.120(3) -0.034(2) -0.0010(17) -0.0198(17)
C1 0.062(3) 0.096(4) 0.079(3) -0.005(3) 0.007(2) 0.001(3)
C2 0.079(3) 0.089(3) 0.075(3) -0.020(3) 0.005(2) 0.001(3)
C3 0.071(3) 0.081(3) 0.077(3) -0.012(3) -0.008(2) -0.012(2)
C4 0.054(2) 0.072(3) 0.063(2) -0.007(2) -0.0033(19) -0.004(2)
C5 0.060(3) 0.091(3) 0.071(3) -0.017(2) -0.002(2) -0.008(2)
C6 0.061(3) 0.099(4) 0.091(3) -0.012(3) -0.009(2) -0.016(3)
C7 0.058(2) 0.083(3) 0.071(3) -0.008(2) -0.006(2) -0.015(2)
C8 0.059(3) 0.092(3) 0.068(3) -0.008(2) -0.003(2) -0.015(2)
C9 0.059(3) 0.083(3) 0.067(3) -0.008(2) -0.002(2) -0.017(2)
C10 0.055(2) 0.092(3) 0.072(3) -0.015(3) -0.003(2) -0.020(2)
C11 0.052(2) 0.083(3) 0.063(2) -0.004(2) -0.0076(19) -0.018(2)
C12 0.048(2) 0.075(3) 0.056(2) -0.004(2) -0.0056(18) -0.013(2)
C13 0.052(2) 0.089(3) 0.064(2) -0.003(2) -0.0108(19) -0.015(2)
C14 0.049(2) 0.098(3) 0.070(3) -0.008(3) -0.001(2) -0.015(2)
C15 0.055(2) 0.086(3) 0.068(3) -0.009(2) -0.005(2) -0.009(2)
O4 0.0526(17) 0.091(2) 0.083(2) -0.0221(17) -0.0043(14) -0.0131(15)
C16 0.057(3) 0.084(3) 0.072(3) -0.010(2) -0.009(2) -0.010(2)
C17 0.077(3) 0.098(4) 0.097(4) -0.025(3) 0.000(3) -0.007(3)

_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 C11 1.271(5) . ?
O2 C13 1.301(5) . ?
O3 C16 1.217(5) . ?
C1 C6 1.362(6) . ?
C1 C2 1.363(7) . ?
C2 C3 1.389(6) . ?
C3 C4 1.380(6) . ?
C4 C5 1.370(6) . ?
C4 C7 1.468(6) . ?
C5 C6 1.391(6) . ?
C7 C8 1.324(6) . ?
C8 C9 1.441(6) . ?
C9 C10 1.320(6) . ?
C10 C11 1.467(5) . ?
C11 C12 1.434(6) . ?
C12 C13 1.411(5) . ?
C12 C16 1.428(6) . ?
C13 C14 1.415(6) . ?
C14 C15 1.321(6) . ?
C15 O4 1.360(5) . ?
C15 C17 1.479(6) . ?
O4 C16 1.404(5) . ?

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
C6 C1 C2 119.6(5) . . ?
C1 C2 C3 119.9(4) . . ?
C4 C3 C2 121.1(4) . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 C7 122.5(4) . . ?
C3 C4 C7 119.3(4) . . ?
C4 C5 C6 120.4(4) . . ?
C1 C6 C5 120.7(4) . . ?
C8 C7 C4 128.7(4) . . ?
C7 C8 C9 123.9(4) . . ?
C10 C9 C8 126.6(4) . . ?
C9 C10 C11 121.1(4) . . ?
O1 C11 C12 118.4(4) . . ?
O1 C11 C10 117.2(4) . . ?
C12 C11 C10 124.3(4) . . ?
C13 C12 C16 118.1(4) . . ?
C13 C12 C11 118.8(4) . . ?
C16 C12 C11 123.1(4) . . ?
O2 C13 C12 120.4(4) . . ?
O2 C13 C14 119.4(4) . . ?
C12 C13 C14 120.2(4) . . ?
C15 C14 C13 120.4(4) . . ?
C14 C15 O4 121.4(4) . . ?
C14 C15 C17 126.9(4) . . ?
O4 C15 C17 111.7(4) . . ?
C15 O4 C16 122.1(3) . . ?
O3 C16 O4 113.6(4) . . ?
O3 C16 C12 128.7(4) . . ?
O4 C16 C12 117.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        65.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.063
