# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1471850'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.
2016-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 O4'
_chemical_formula_sum            'C17 H14 O4'
_chemical_formula_weight         282.28

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_space_group_name_Hall           '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1218(5)
_cell_length_b                   27.7422(16)
_cell_length_c                   12.2315(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.062(2)
_cell_angle_gamma                90.00
_cell_volume                     2745.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9486
_cell_measurement_theta_min      3.96
_cell_measurement_theta_max      68.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8447
_exptl_absorpt_correction_T_max  0.9441
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 VENTURE'
_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            32969
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         68.29
_reflns_number_total             5019
_reflns_number_gt                4507
_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)+(0.0656P)²+0.3931P] 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_number_reflns         5019
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
O2 O 0.75326(10) 0.30893(3) 0.87085(6) 0.0423(2) Uani 1 1 d . . .
O6 O 0.70063(10) 0.29882(3) 0.42422(6) 0.0425(2) Uani 1 1 d . . .
O3 O 0.79216(11) 0.23154(3) 0.84747(7) 0.0500(2) Uani 1 1 d . . .
O7 O 0.70711(12) 0.21989(3) 0.41995(7) 0.0519(2) Uani 1 1 d . . .
O1 O 0.68687(11) 0.47835(3) 0.90692(8) 0.0541(2) Uani 1 1 d . . .
O5 O 0.68889(12) 0.47061(3) 0.41357(8) 0.0565(3) Uani 1 1 d . . .
O8 O 0.39516(12) 0.24931(4) 0.74044(8) 0.0586(3) Uani 1 1 d . . .
H8A H 0.3433 0.2499 0.7950 0.088 Uiso 1 1 calc R . .
O4 O 0.45814(13) 0.23198(3) 1.16447(8) 0.0600(3) Uani 1 1 d . . .
H4A H 0.4071 0.2278 1.2186 0.090 Uiso 1 1 calc R . .
C28 C 0.55387(13) 0.34192(4) 0.55640(9) 0.0372(3) Uani 1 1 d . . .
C11 C 0.59969(13) 0.33920(4) 1.01606(9) 0.0373(3) Uani 1 1 d . . .
C12 C 0.68944(13) 0.34679(4) 0.92597(9) 0.0365(2) Uani 1 1 d . . .
C14 C 0.57225(13) 0.29008(4) 1.04917(9) 0.0365(2) Uani 1 1 d . . .
C29 C 0.64986(14) 0.34143(4) 0.46715(9) 0.0378(3) Uani 1 1 d . . .
C31 C 0.51204(13) 0.29634(4) 0.60391(9) 0.0366(2) Uani 1 1 d . . .
C16 C 0.72757(14) 0.26165(4) 0.90033(9) 0.0386(3) Uani 1 1 d . . .
C32 C 0.56435(14) 0.25512(4) 0.56078(9) 0.0400(3) Uani 1 1 d . . .
H32A H 0.5385 0.2259 0.5925 0.048 Uiso 1 1 calc R . .
C34 C 0.40670(15) 0.29607(4) 0.69866(9) 0.0431(3) Uani 1 1 d . . .
H34A H 0.4545 0.3173 0.7559 0.052 Uiso 1 1 calc R . .
H34B H 0.2971 0.3079 0.6746 0.052 Uiso 1 1 calc R . .
C15 C 0.63070(14) 0.25365(4) 0.99147(9) 0.0403(3) Uani 1 1 d . . .
H15A H 0.6077 0.2221 1.0112 0.048 Uiso 1 1 calc R . .
C13 C 0.72110(14) 0.39219(4) 0.88544(10) 0.0423(3) Uani 1 1 d . . .
H13A H 0.7809 0.3959 0.8245 0.051 Uiso 1 1 calc R . .
C27 C 0.50527(15) 0.38732(4) 0.59265(10) 0.0448(3) Uani 1 1 d . . .
H27A H 0.4402 0.3892 0.6514 0.054 Uiso 1 1 calc R . .
C33 C 0.65960(14) 0.25488(4) 0.46652(9) 0.0404(3) Uani 1 1 d . . .
C10 C 0.53950(15) 0.38054(4) 1.06601(10) 0.0445(3) Uani 1 1 d . . .
H10A H 0.4781 0.3770 1.1262 0.053 Uiso 1 1 calc R . .
C30 C 0.69898(15) 0.38288(4) 0.41588(10) 0.0434(3) Uani 1 1 d . . .
H30A H 0.7632 0.3812 0.3567 0.052 Uiso 1 1 calc R . .
C18 C 0.82344(16) 0.52332(4) 0.29697(10) 0.0473(3) Uani 1 1 d . . .
C8 C 0.66165(14) 0.43189(4) 0.93770(11) 0.0433(3) Uani 1 1 d . . .
C17 C 0.47919(16) 0.28159(5) 1.14793(10) 0.0456(3) Uani 1 1 d . . .
H17A H 0.5395 0.2956 1.2122 0.055 Uiso 1 1 calc R . .
H17B H 0.3720 0.2971 1.1376 0.055 Uiso 1 1 calc R . .
C1 C 0.81638(16) 0.53784(4) 0.80077(11) 0.0470(3) Uani 1 1 d . . .
C25 C 0.64987(15) 0.42690(4) 0.45516(10) 0.0447(3) Uani 1 1 d . . .
C26 C 0.55143(16) 0.42896(5) 0.54368(11) 0.0482(3) Uani 1 1 d . . .
H26A H 0.5175 0.4586 0.5691 0.058 Uiso 1 1 calc R . .
C19 C 0.76068(17) 0.54345(5) 0.19887(11) 0.0539(3) Uani 1 1 d . . .
H19A H 0.6933 0.5251 0.1495 0.065 Uiso 1 1 calc R . .
C21 C 0.89542(16) 0.61815(5) 0.24513(12) 0.0542(3) Uani 1 1 d . . .
H21A H 0.9203 0.6498 0.2275 0.065 Uiso 1 1 calc R . .
C9 C 0.56902(16) 0.42581(5) 1.02824(11) 0.0473(3) Uani 1 1 d . . .
H9A H 0.5277 0.4526 1.0626 0.057 Uiso 1 1 calc R . .
C7 C 0.78622(18) 0.48495(5) 0.81643(12) 0.0544(3) Uani 1 1 d . . .
H7A H 0.7298 0.4715 0.7501 0.065 Uiso 1 1 calc R . .
H7B H 0.8908 0.4683 0.8311 0.065 Uiso 1 1 calc R . .
C24 C 0.78987(18) 0.47154(5) 0.32327(12) 0.0546(3) Uani 1 1 d . . .
H24A H 0.7332 0.4557 0.2600 0.066 Uiso 1 1 calc R . .
H24B H 0.8930 0.4547 0.3426 0.066 Uiso 1 1 calc R . .
C20 C 0.79697(18) 0.59071(5) 0.17316(12) 0.0585(4) Uani 1 1 d . . .
H20A H 0.7542 0.6038 0.1067 0.070 Uiso 1 1 calc R . .
C4 C 0.88895(19) 0.63397(5) 0.76418(13) 0.0608(4) Uani 1 1 d . . .
H4B H 0.9139 0.6661 0.7518 0.073 Uiso 1 1 calc R . .
C2 C 0.74778(19) 0.56129(5) 0.70907(13) 0.0626(4) Uani 1 1 d . . .
H2A H 0.6766 0.5448 0.6584 0.075 Uiso 1 1 calc R . .
C23 C 0.92114(19) 0.55161(5) 0.36914(12) 0.0602(4) Uani 1 1 d . . .
H23A H 0.9635 0.5388 0.4361 0.072 Uiso 1 1 calc R . .
C22 C 0.95693(19) 0.59882(5) 0.34304(13) 0.0626(4) Uani 1 1 d . . .
H22A H 1.0232 0.6175 0.3924 0.075 Uiso 1 1 calc R . .
C3 C 0.7835(2) 0.60927(5) 0.69115(14) 0.0686(4) Uani 1 1 d . . .
H3A H 0.7353 0.6248 0.6290 0.082 Uiso 1 1 calc R . .
C6 C 0.9209(2) 0.56298(5) 0.87432(12) 0.0639(4) Uani 1 1 d . . .
H6A H 0.9676 0.5477 0.9373 0.077 Uiso 1 1 calc R . .
C5 C 0.9573(2) 0.61070(5) 0.85585(14) 0.0704(4) Uani 1 1 d . . .
H5A H 1.0290 0.6272 0.9062 0.085 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
O2 C12 1.3740(13) . ?
O2 C16 1.3812(14) . ?
O6 C29 1.3718(13) . ?
O6 C33 1.3765(14) . ?
O3 C16 1.2045(14) . ?
O7 C33 1.2062(14) . ?
O1 C8 1.3632(14) . ?
O1 C7 1.4378(16) . ?
O5 C25 1.3632(14) . ?
O5 C24 1.4329(15) . ?
O8 C34 1.4005(15) . ?
O8 H8A 0.8200 . ?
O4 C17 1.4037(16) . ?
O4 H4A 0.8200 . ?
C28 C29 1.3963(15) . ?
C28 C27 1.4033(16) . ?
C28 C31 1.4448(16) . ?
C11 C12 1.3898(15) . ?
C11 C10 1.4073(16) . ?
C11 C14 1.4445(16) . ?
C12 C13 1.3859(16) . ?
C14 C15 1.3431(16) . ?
C14 C17 1.4990(15) . ?
C29 C30 1.3851(16) . ?
C31 C32 1.3438(16) . ?
C31 C34 1.5000(14) . ?
C16 C15 1.4373(16) . ?
C32 C33 1.4440(15) . ?
C32 H32A 0.9300 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C15 H15A 0.9300 . ?
C13 C8 1.3817(16) . ?
C13 H13A 0.9300 . ?
C27 C26 1.3688(17) . ?
C27 H27A 0.9300 . ?
C10 C9 1.3666(18) . ?
C10 H10A 0.9300 . ?
C30 C25 1.3839(17) . ?
C30 H30A 0.9300 . ?
C18 C23 1.3788(19) . ?
C18 C19 1.3796(18) . ?
C18 C24 1.5025(17) . ?
C8 C9 1.4029(17) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C1 C6 1.3714(19) . ?
C1 C2 1.3716(19) . ?
C1 C7 1.5027(17) . ?
C25 C26 1.4027(17) . ?
C26 H26A 0.9300 . ?
C19 C20 1.3861(19) . ?
C19 H19A 0.9300 . ?
C21 C22 1.366(2) . ?
C21 C20 1.367(2) . ?
C21 H21A 0.9300 . ?
C9 H9A 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C20 H20A 0.9300 . ?
C4 C3 1.366(2) . ?
C4 C5 1.368(2) . ?
C4 H4B 0.9300 . ?
C2 C3 1.384(2) . ?
C2 H2A 0.9300 . ?
C23 C22 1.385(2) . ?
C23 H23A 0.9300 . ?
C22 H22A 0.9300 . ?
C3 H3A 0.9300 . ?
C6 C5 1.380(2) . ?
C6 H6A 0.9300 . ?
C5 H5A 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
C12 O2 C16 121.71(9) . . ?
C29 O6 C33 121.89(9) . . ?
C8 O1 C7 116.19(9) . . ?
C25 O5 C24 118.12(10) . . ?
C34 O8 H8A 109.5 . . ?
C17 O4 H4A 109.5 . . ?
C29 C28 C27 116.60(10) . . ?
C29 C28 C31 118.25(10) . . ?
C27 C28 C31 125.15(10) . . ?
C12 C11 C10 116.57(11) . . ?
C12 C11 C14 118.03(10) . . ?
C10 C11 C14 125.38(10) . . ?
O2 C12 C13 115.42(10) . . ?
O2 C12 C11 121.34(10) . . ?
C13 C12 C11 123.25(10) . . ?
C15 C14 C11 119.48(10) . . ?
C15 C14 C17 122.13(11) . . ?
C11 C14 C17 118.38(10) . . ?
O6 C29 C30 115.70(10) . . ?
O6 C29 C28 121.00(10) . . ?
C30 C29 C28 123.29(10) . . ?
C32 C31 C28 119.55(10) . . ?
C32 C31 C34 121.39(10) . . ?
C28 C31 C34 119.04(10) . . ?
O3 C16 O2 115.82(10) . . ?
O3 C16 C15 127.11(11) . . ?
O2 C16 C15 117.05(10) . . ?
C31 C32 C33 121.84(11) . . ?
C31 C32 H32A 119.1 . . ?
C33 C32 H32A 119.1 . . ?
O8 C34 C31 110.33(10) . . ?
O8 C34 H34A 109.6 . . ?
C31 C34 H34A 109.6 . . ?
O8 C34 H34B 109.6 . . ?
C31 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
C14 C15 C16 122.30(11) . . ?
C14 C15 H15A 118.9 . . ?
C16 C15 H15A 118.9 . . ?
C8 C13 C12 118.39(11) . . ?
C8 C13 H13A 120.8 . . ?
C12 C13 H13A 120.8 . . ?
C26 C27 C28 121.57(11) . . ?
C26 C27 H27A 119.2 . . ?
C28 C27 H27A 119.2 . . ?
O7 C33 O6 115.91(10) . . ?
O7 C33 C32 126.66(11) . . ?
O6 C33 C32 117.42(10) . . ?
C9 C10 C11 121.61(11) . . ?
C9 C10 H10A 119.2 . . ?
C11 C10 H10A 119.2 . . ?
C29 C30 C25 118.16(11) . . ?
C29 C30 H30A 120.9 . . ?
C25 C30 H30A 120.9 . . ?
C23 C18 C19 118.30(12) . . ?
C23 C18 C24 120.81(12) . . ?
C19 C18 C24 120.87(12) . . ?
O1 C8 C13 123.96(11) . . ?
O1 C8 C9 115.84(10) . . ?
C13 C8 C9 120.20(11) . . ?
O4 C17 C14 110.29(10) . . ?
O4 C17 H17A 109.6 . . ?
C14 C17 H17A 109.6 . . ?
O4 C17 H17B 109.6 . . ?
C14 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C6 C1 C2 118.58(12) . . ?
C6 C1 C7 120.75(12) . . ?
C2 C1 C7 120.55(13) . . ?
O5 C25 C30 124.88(11) . . ?
O5 C25 C26 114.76(11) . . ?
C30 C25 C26 120.36(11) . . ?
C27 C26 C25 120.01(11) . . ?
C27 C26 H26A 120.0 . . ?
C25 C26 H26A 120.0 . . ?
C18 C19 C20 120.69(13) . . ?
C18 C19 H19A 119.7 . . ?
C20 C19 H19A 119.7 . . ?
C22 C21 C20 119.59(13) . . ?
C22 C21 H21A 120.2 . . ?
C20 C21 H21A 120.2 . . ?
C10 C9 C8 119.98(11) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
O1 C7 C1 109.35(10) . . ?
O1 C7 H7A 109.8 . . ?
C1 C7 H7A 109.8 . . ?
O1 C7 H7B 109.8 . . ?
C1 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
O5 C24 C18 108.01(10) . . ?
O5 C24 H24A 110.1 . . ?
C18 C24 H24A 110.1 . . ?
O5 C24 H24B 110.1 . . ?
C18 C24 H24B 110.1 . . ?
H24A C24 H24B 108.4 . . ?
C21 C20 C19 120.31(13) . . ?
C21 C20 H20A 119.8 . . ?
C19 C20 H20A 119.8 . . ?
C3 C4 C5 119.00(13) . . ?
C3 C4 H4B 120.5 . . ?
C5 C4 H4B 120.5 . . ?
C1 C2 C3 120.67(14) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C18 C23 C22 120.75(13) . . ?
C18 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C21 C22 C23 120.36(14) . . ?
C21 C22 H22A 119.8 . . ?
C23 C22 H22A 119.8 . . ?
C4 C3 C2 120.46(14) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C1 C6 C5 120.66(14) . . ?
C1 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C4 C5 C6 120.63(14) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15A O4 0.93 2.34 2.7068(14) 103.2 .
C32 H32A O8 0.93 2.33 2.6974(14) 103.2 .
O4 H4A O2 0.82 2.54 3.3422(11) 164.6 4_566
O4 H4A O3 0.82 2.21 2.8955(13) 141.0 4_566
O8 H8A O6 0.82 2.45 3.1557(12) 145.1 4_566
O8 H8A O7 0.82 2.14 2.9113(12) 157.9 4_566

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        68.29
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
