# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_C13-a _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 O5' _chemical_formula_sum 'C21 H18 O5' _chemical_formula_weight 350.35 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_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 11.6513(11) _cell_length_b 10.1496(9) _cell_length_c 14.4797(14) _cell_angle_alpha 90.00 _cell_angle_beta 102.588(2) _cell_angle_gamma 90.00 _cell_volume 1671.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1265 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 25.41 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9823 _exptl_absorpt_correction_T_max 0.9882 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 10313 _diffrn_reflns_av_R_equivalents 0.0993 _diffrn_reflns_av_sigmaI/netI 0.1094 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.03 _reflns_number_total 3291 _reflns_number_gt 1519 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0593P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3291 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1596 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1716 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 C1 C 0.8849(3) -0.0439(3) 0.3422(3) 0.0292(9) Uani 1 1 d . . . C2 C 0.8591(3) -0.0019(4) 0.4268(3) 0.0336(9) Uani 1 1 d . . . O1 O 0.8399(3) -0.0872(2) 0.49386(18) 0.0429(8) Uani 1 1 d . . . H1 H 0.8444 -0.1649 0.4749 0.064 Uiso 1 1 calc R . . C3 C 0.8500(3) 0.1353(4) 0.4478(3) 0.0343(10) Uani 1 1 d . . . C4 C 0.8188(3) 0.1778(4) 0.5314(3) 0.0408(11) Uani 1 1 d . . . H4 H 0.8032 0.1146 0.5755 0.049 Uiso 1 1 calc R . . C5 C 0.8107(4) 0.3090(4) 0.5500(3) 0.0471(12) Uani 1 1 d . . . H5 H 0.7885 0.3364 0.6064 0.057 Uiso 1 1 calc R . . C6 C 0.8347(4) 0.4031(4) 0.4865(3) 0.0459(11) Uani 1 1 d . . . H6 H 0.8304 0.4941 0.5008 0.055 Uiso 1 1 calc R . . C7 C 0.8645(3) 0.3658(4) 0.4040(3) 0.0378(10) Uani 1 1 d . . . H7 H 0.8813 0.4308 0.3616 0.045 Uiso 1 1 calc R . . C8 C 0.8703(3) 0.2310(4) 0.3817(3) 0.0333(9) Uani 1 1 d . . . C9 C 0.8959(3) 0.1838(4) 0.2969(3) 0.0306(9) Uani 1 1 d . . . O2 O 0.9160(2) 0.2689(2) 0.22742(18) 0.0365(7) Uani 1 1 d . . . C10 C 0.9169(3) 0.1867(3) 0.1453(3) 0.0329(10) Uani 1 1 d . . . H10 H 0.8388 0.1921 0.1001 0.040 Uiso 1 1 calc R . . C11 C 0.9397(3) 0.0437(3) 0.1808(3) 0.0290(9) Uani 1 1 d . . . H11 H 0.8853 -0.0173 0.1379 0.035 Uiso 1 1 calc R . . C12 C 0.9032(3) 0.0538(3) 0.2751(3) 0.0295(9) Uani 1 1 d . . . C13 C 0.8917(3) -0.1861(4) 0.3256(3) 0.0329(10) Uani 1 1 d . . . O3 O 0.8783(2) -0.2713(2) 0.38291(19) 0.0421(7) Uani 1 1 d . . . O4 O 0.9130(2) -0.2166(2) 0.24149(19) 0.0397(7) Uani 1 1 d . . . C14 C 0.9263(4) -0.3551(3) 0.2223(3) 0.0471(12) Uani 1 1 d . . . H14A H 0.9902 -0.3923 0.2707 0.071 Uiso 1 1 calc R . . H14B H 0.9449 -0.3652 0.1599 0.071 Uiso 1 1 calc R . . H14C H 0.8528 -0.4015 0.2234 0.071 Uiso 1 1 calc R . . O5 O 1.0043(2) 0.2294(2) 0.10101(18) 0.0372(7) Uani 1 1 d . . . C15 C 0.9807(3) 0.3542(4) 0.0565(3) 0.0399(10) Uani 1 1 d . . . H15A H 0.9041 0.3517 0.0120 0.060 Uiso 1 1 calc R . . H15B H 1.0421 0.3751 0.0221 0.060 Uiso 1 1 calc R . . H15C H 0.9796 0.4219 0.1046 0.060 Uiso 1 1 calc R . . C16 C 1.0654(3) -0.0018(3) 0.1901(3) 0.0282(9) Uani 1 1 d . . . C17 C 1.1546(3) 0.0436(3) 0.2622(3) 0.0315(9) Uani 1 1 d . . . H17 H 1.1369 0.1050 0.3066 0.038 Uiso 1 1 calc R . . C18 C 1.2693(3) 0.0010(4) 0.2709(3) 0.0413(11) Uani 1 1 d . . . H18 H 1.3296 0.0339 0.3206 0.050 Uiso 1 1 calc R . . C19 C 1.2961(4) -0.0892(4) 0.2073(3) 0.0448(11) Uani 1 1 d . . . H19 H 1.3746 -0.1195 0.2137 0.054 Uiso 1 1 calc R . . C20 C 1.2086(4) -0.1348(4) 0.1347(3) 0.0422(11) Uani 1 1 d . . . H20 H 1.2268 -0.1967 0.0908 0.051 Uiso 1 1 calc R . . C21 C 1.0933(3) -0.0908(4) 0.1254(3) 0.0373(10) Uani 1 1 d . . . H21 H 1.0335 -0.1217 0.0745 0.045 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 C1 0.028(2) 0.026(2) 0.034(2) 0.0022(17) 0.0077(19) -0.0017(16) C2 0.032(2) 0.036(2) 0.035(2) 0.0080(19) 0.011(2) -0.0059(19) O1 0.0559(19) 0.0384(17) 0.0388(17) 0.0062(14) 0.0202(16) -0.0040(15) C3 0.032(2) 0.039(2) 0.033(2) -0.0023(19) 0.009(2) 0.0010(18) C4 0.040(2) 0.045(3) 0.039(3) 0.000(2) 0.012(2) -0.001(2) C5 0.052(3) 0.055(3) 0.038(3) -0.009(2) 0.018(2) 0.002(2) C6 0.055(3) 0.040(3) 0.045(3) -0.008(2) 0.016(2) 0.005(2) C7 0.047(3) 0.032(2) 0.037(3) 0.0008(19) 0.014(2) 0.0038(19) C8 0.034(2) 0.035(2) 0.032(2) -0.0008(19) 0.010(2) -0.0002(18) C9 0.031(2) 0.031(2) 0.031(2) 0.0045(18) 0.010(2) -0.0027(17) O2 0.0543(18) 0.0258(14) 0.0346(16) 0.0011(12) 0.0209(15) 0.0004(13) C10 0.039(2) 0.031(2) 0.031(2) 0.0006(18) 0.013(2) -0.0007(18) C11 0.030(2) 0.030(2) 0.026(2) -0.0020(16) 0.0027(18) 0.0004(17) C12 0.032(2) 0.025(2) 0.032(2) 0.0026(17) 0.0094(19) -0.0001(17) C13 0.029(2) 0.033(2) 0.037(3) 0.004(2) 0.008(2) -0.0007(18) O3 0.0502(18) 0.0360(16) 0.0426(18) 0.0087(14) 0.0153(15) -0.0034(14) O4 0.0489(18) 0.0280(15) 0.0458(18) -0.0031(13) 0.0179(16) -0.0011(13) C14 0.061(3) 0.020(2) 0.063(3) -0.004(2) 0.020(3) 0.002(2) O5 0.0465(17) 0.0298(15) 0.0398(17) 0.0080(12) 0.0195(15) 0.0029(13) C15 0.049(3) 0.032(2) 0.039(3) 0.0052(19) 0.010(2) -0.001(2) C16 0.033(2) 0.025(2) 0.029(2) 0.0034(17) 0.0101(19) 0.0016(17) C17 0.034(2) 0.033(2) 0.027(2) 0.0001(17) 0.006(2) -0.0016(18) C18 0.034(2) 0.047(3) 0.043(3) 0.006(2) 0.007(2) 0.004(2) C19 0.043(3) 0.041(3) 0.057(3) 0.013(2) 0.025(3) 0.009(2) C20 0.038(3) 0.040(2) 0.052(3) -0.006(2) 0.016(2) 0.006(2) C21 0.042(3) 0.037(2) 0.035(2) -0.0026(19) 0.014(2) -0.001(2) _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 C2 1.390(5) . ? C1 C12 1.436(5) . ? C1 C13 1.469(5) . ? C2 O1 1.355(4) . ? C2 C3 1.434(5) . ? O1 H1 0.8400 . ? C3 C4 1.406(5) . ? C3 C8 1.420(5) . ? C4 C5 1.366(5) . ? C4 H4 0.9500 . ? C5 C6 1.396(5) . ? C5 H5 0.9500 . ? C6 C7 1.368(5) . ? C6 H6 0.9500 . ? C7 C8 1.411(5) . ? C7 H7 0.9500 . ? C8 C9 1.409(5) . ? C9 C12 1.364(5) . ? C9 O2 1.383(4) . ? O2 C10 1.454(4) . ? C10 O5 1.385(4) . ? C10 C11 1.543(5) . ? C10 H10 1.0000 . ? C11 C16 1.514(5) . ? C11 C12 1.519(5) . ? C11 H11 1.0000 . ? C13 O3 1.232(4) . ? C13 O4 1.331(4) . ? O4 C14 1.447(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O5 C15 1.421(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.381(5) . ? C16 C21 1.391(5) . ? C17 C18 1.384(5) . ? C17 H17 0.9500 . ? C18 C19 1.381(5) . ? C18 H18 0.9500 . ? C19 C20 1.376(5) . ? C19 H19 0.9500 . ? C20 C21 1.394(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? 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 C2 C1 C12 118.5(3) . . ? C2 C1 C13 118.4(3) . . ? C12 C1 C13 123.1(3) . . ? O1 C2 C1 122.5(3) . . ? O1 C2 C3 115.9(3) . . ? C1 C2 C3 121.6(3) . . ? C2 O1 H1 109.5 . . ? C4 C3 C8 118.9(4) . . ? C4 C3 C2 121.7(4) . . ? C8 C3 C2 119.4(3) . . ? C5 C4 C3 120.7(4) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.4(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 120.7(4) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 120.1(4) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 124.0(3) . . ? C9 C8 C3 116.9(3) . . ? C7 C8 C3 119.1(3) . . ? C12 C9 O2 114.0(3) . . ? C12 C9 C8 124.5(3) . . ? O2 C9 C8 121.5(3) . . ? C9 O2 C10 105.6(3) . . ? O5 C10 O2 109.7(3) . . ? O5 C10 C11 111.0(3) . . ? O2 C10 C11 107.4(3) . . ? O5 C10 H10 109.6 . . ? O2 C10 H10 109.6 . . ? C11 C10 H10 109.6 . . ? C16 C11 C12 113.3(3) . . ? C16 C11 C10 114.2(3) . . ? C12 C11 C10 100.1(3) . . ? C16 C11 H11 109.6 . . ? C12 C11 H11 109.6 . . ? C10 C11 H11 109.6 . . ? C9 C12 C1 119.0(3) . . ? C9 C12 C11 108.5(3) . . ? C1 C12 C11 132.3(3) . . ? O3 C13 O4 122.0(3) . . ? O3 C13 C1 124.0(4) . . ? O4 C13 C1 113.9(3) . . ? C13 O4 C14 116.8(3) . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 O5 C15 113.6(3) . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 118.6(3) . . ? C17 C16 C11 121.3(3) . . ? C21 C16 C11 120.1(3) . . ? C16 C17 C18 121.1(4) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C19 C18 C17 120.1(4) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 119.6(4) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 120.3(4) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C16 C21 C20 120.3(4) . . ? C16 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? 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 C12 C1 C2 O1 179.6(3) . . . . ? C13 C1 C2 O1 -0.2(6) . . . . ? C12 C1 C2 C3 0.3(6) . . . . ? C13 C1 C2 C3 -179.5(3) . . . . ? O1 C2 C3 C4 -2.2(5) . . . . ? C1 C2 C3 C4 177.1(4) . . . . ? O1 C2 C3 C8 179.2(3) . . . . ? C1 C2 C3 C8 -1.4(6) . . . . ? C8 C3 C4 C5 -1.5(6) . . . . ? C2 C3 C4 C5 180.0(4) . . . . ? C3 C4 C5 C6 -0.8(6) . . . . ? C4 C5 C6 C7 1.3(7) . . . . ? C5 C6 C7 C8 0.5(6) . . . . ? C6 C7 C8 C9 177.5(4) . . . . ? C6 C7 C8 C3 -2.8(6) . . . . ? C4 C3 C8 C9 -177.1(4) . . . . ? C2 C3 C8 C9 1.5(5) . . . . ? C4 C3 C8 C7 3.2(6) . . . . ? C2 C3 C8 C7 -178.2(3) . . . . ? C7 C8 C9 C12 179.1(4) . . . . ? C3 C8 C9 C12 -0.6(6) . . . . ? C7 C8 C9 O2 -0.9(6) . . . . ? C3 C8 C9 O2 179.4(3) . . . . ? C12 C9 O2 C10 10.4(4) . . . . ? C8 C9 O2 C10 -169.6(3) . . . . ? C9 O2 C10 O5 -140.4(3) . . . . ? C9 O2 C10 C11 -19.8(4) . . . . ? O5 C10 C11 C16 19.3(4) . . . . ? O2 C10 C11 C16 -100.6(3) . . . . ? O5 C10 C11 C12 140.6(3) . . . . ? O2 C10 C11 C12 20.8(4) . . . . ? O2 C9 C12 C1 179.5(3) . . . . ? C8 C9 C12 C1 -0.5(6) . . . . ? O2 C9 C12 C11 3.5(4) . . . . ? C8 C9 C12 C11 -176.5(4) . . . . ? C2 C1 C12 C9 0.6(6) . . . . ? C13 C1 C12 C9 -179.6(3) . . . . ? C2 C1 C12 C11 175.5(4) . . . . ? C13 C1 C12 C11 -4.7(6) . . . . ? C16 C11 C12 C9 107.2(4) . . . . ? C10 C11 C12 C9 -14.8(4) . . . . ? C16 C11 C12 C1 -68.1(5) . . . . ? C10 C11 C12 C1 170.0(4) . . . . ? C2 C1 C13 O3 -1.5(6) . . . . ? C12 C1 C13 O3 178.7(4) . . . . ? C2 C1 C13 O4 177.9(3) . . . . ? C12 C1 C13 O4 -1.9(5) . . . . ? O3 C13 O4 C14 -3.4(5) . . . . ? C1 C13 O4 C14 177.2(3) . . . . ? O2 C10 O5 C15 -68.9(4) . . . . ? C11 C10 O5 C15 172.6(3) . . . . ? C12 C11 C16 C17 -40.7(5) . . . . ? C10 C11 C16 C17 73.0(4) . . . . ? C12 C11 C16 C21 139.4(3) . . . . ? C10 C11 C16 C21 -106.9(4) . . . . ? C21 C16 C17 C18 -0.5(5) . . . . ? C11 C16 C17 C18 179.5(3) . . . . ? C16 C17 C18 C19 -0.6(6) . . . . ? C17 C18 C19 C20 1.0(6) . . . . ? C18 C19 C20 C21 -0.2(6) . . . . ? C17 C16 C21 C20 1.3(5) . . . . ? C11 C16 C21 C20 -178.8(3) . . . . ? C19 C20 C21 C16 -1.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.268 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 948207' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_T14 _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 O5' _chemical_formula_sum 'C21 H18 O5' _chemical_formula_weight 350.35 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' 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' '-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 18.757(2) _cell_length_b 10.0250(13) _cell_length_c 19.754(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.543(3) _cell_angle_gamma 90.00 _cell_volume 3378.8(7) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 3922 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 28.24 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 12307 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.34 _reflns_number_total 4212 _reflns_number_gt 2137 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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/[\s^2^(Fo^2^)+(0.0676P)^2^+2.0152P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4212 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1676 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 C1 C 0.04958(12) 0.0332(2) 0.09215(12) 0.0342(5) Uani 1 1 d . . . C2 C 0.03309(13) -0.0957(2) 0.10744(13) 0.0369(5) Uani 1 1 d . . . O1 O 0.07019(10) -0.20398(16) 0.09739(11) 0.0491(5) Uani 1 1 d . . . H1 H 0.1062 -0.1797 0.0853 0.074 Uiso 1 1 calc R . . C3 C -0.02584(13) -0.1215(2) 0.13364(12) 0.0363(5) Uani 1 1 d . . . C4 C -0.04184(14) -0.2518(2) 0.15052(14) 0.0454(6) Uani 1 1 d . . . H4 H -0.0133 -0.3250 0.1437 0.054 Uiso 1 1 calc R . . C5 C -0.09790(15) -0.2738(3) 0.17660(14) 0.0500(7) Uani 1 1 d . . . H5 H -0.1078 -0.3622 0.1879 0.060 Uiso 1 1 calc R . . C6 C -0.14098(15) -0.1674(3) 0.18688(14) 0.0487(7) Uani 1 1 d . . . H6 H -0.1795 -0.1838 0.2054 0.058 Uiso 1 1 calc R . . C7 C -0.12756(14) -0.0397(3) 0.17016(13) 0.0413(6) Uani 1 1 d . . . H7 H -0.1575 0.0318 0.1764 0.050 Uiso 1 1 calc R . . C8 C -0.06990(13) -0.0137(2) 0.14390(12) 0.0362(5) Uani 1 1 d . . . C9 C -0.05215(13) 0.1147(2) 0.12584(13) 0.0351(5) Uani 1 1 d . . . O2 O -0.09199(9) 0.22653(15) 0.13197(9) 0.0414(4) Uani 1 1 d . . . C10 C -0.06830(14) 0.3337(2) 0.09707(13) 0.0388(6) Uani 1 1 d . . . H10 H -0.0589 0.4169 0.1275 0.047 Uiso 1 1 calc R . . C11 C 0.00748(13) 0.2898(2) 0.09117(13) 0.0366(5) Uani 1 1 d . . . H11 H 0.0026 0.3075 0.0396 0.044 Uiso 1 1 calc R . . C12 C 0.00502(13) 0.1403(2) 0.10257(12) 0.0342(5) Uani 1 1 d . . . C13 C 0.11209(13) 0.0528(2) 0.06722(13) 0.0362(5) Uani 1 1 d . . . O3 O 0.15276(10) -0.03712(17) 0.05985(10) 0.0499(5) Uani 1 1 d . . . O4 O 0.12194(9) 0.17900(16) 0.05280(10) 0.0442(4) Uani 1 1 d . . . C14 C 0.18574(15) 0.2071(3) 0.03303(15) 0.0505(7) Uani 1 1 d . . . H14A H 0.2351 0.1787 0.0734 0.076 Uiso 1 1 calc R . . H14B H 0.1877 0.3032 0.0247 0.076 Uiso 1 1 calc R . . H14C H 0.1781 0.1587 -0.0126 0.076 Uiso 1 1 calc R . . O5 O -0.12525(10) 0.35584(17) 0.02548(10) 0.0475(5) Uani 1 1 d . . . C15 C -0.19633(15) 0.4097(3) 0.02437(17) 0.0581(8) Uani 1 1 d . . . H15A H -0.2206 0.3443 0.0451 0.087 Uiso 1 1 calc R . . H15B H -0.2324 0.4303 -0.0270 0.087 Uiso 1 1 calc R . . H15C H -0.1847 0.4914 0.0543 0.087 Uiso 1 1 calc R . . C16 C 0.08031(14) 0.3601(2) 0.14702(13) 0.0369(5) Uani 1 1 d . . . C17 C 0.11693(15) 0.3186(3) 0.21958(14) 0.0477(6) Uani 1 1 d . . . H17 H 0.0970 0.2437 0.2357 0.057 Uiso 1 1 calc R . . C18 C 0.18267(17) 0.3845(3) 0.26975(16) 0.0551(7) Uani 1 1 d . . . H18 H 0.2077 0.3544 0.3198 0.066 Uiso 1 1 calc R . . C19 C 0.21161(16) 0.4936(3) 0.24686(17) 0.0543(7) Uani 1 1 d . . . H19 H 0.2569 0.5385 0.2810 0.065 Uiso 1 1 calc R . . C20 C 0.17496(15) 0.5372(3) 0.17487(17) 0.0529(7) Uani 1 1 d . . . H20 H 0.1944 0.6130 0.1591 0.063 Uiso 1 1 calc R . . C21 C 0.10960(15) 0.4705(2) 0.12510(15) 0.0468(6) Uani 1 1 d . . . H21 H 0.0845 0.5011 0.0752 0.056 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 C1 0.0285(12) 0.0377(13) 0.0353(12) -0.0023(10) 0.0121(10) 0.0029(10) C2 0.0332(12) 0.0336(13) 0.0428(14) -0.0003(10) 0.0146(11) 0.0041(10) O1 0.0459(11) 0.0387(10) 0.0673(12) 0.0012(9) 0.0281(10) 0.0100(8) C3 0.0308(12) 0.0374(13) 0.0349(13) 0.0010(10) 0.0079(10) 0.0005(10) C4 0.0411(14) 0.0414(14) 0.0514(16) 0.0029(12) 0.0170(12) -0.0014(11) C5 0.0502(16) 0.0441(15) 0.0509(16) 0.0057(12) 0.0162(13) -0.0070(12) C6 0.0427(15) 0.0594(17) 0.0446(15) 0.0014(13) 0.0188(12) -0.0104(13) C7 0.0377(13) 0.0465(15) 0.0436(14) -0.0028(11) 0.0207(11) -0.0038(11) C8 0.0318(12) 0.0410(13) 0.0330(12) -0.0014(10) 0.0107(10) -0.0014(10) C9 0.0333(12) 0.0362(12) 0.0386(13) -0.0009(10) 0.0177(11) 0.0039(10) O2 0.0438(10) 0.0383(9) 0.0525(10) 0.0026(8) 0.0302(9) 0.0074(7) C10 0.0417(14) 0.0351(13) 0.0417(14) 0.0034(10) 0.0192(12) 0.0056(10) C11 0.0375(13) 0.0369(13) 0.0380(13) 0.0020(10) 0.0184(11) 0.0025(10) C12 0.0326(12) 0.0354(12) 0.0355(12) 0.0001(10) 0.0150(10) 0.0009(10) C13 0.0306(12) 0.0405(13) 0.0352(13) -0.0025(10) 0.0114(10) 0.0024(10) O3 0.0394(10) 0.0501(11) 0.0651(12) -0.0026(9) 0.0268(9) 0.0094(8) O4 0.0402(10) 0.0448(10) 0.0582(11) -0.0015(8) 0.0308(9) -0.0025(8) C14 0.0399(14) 0.0608(17) 0.0596(17) -0.0034(13) 0.0295(13) -0.0077(12) O5 0.0402(10) 0.0519(11) 0.0522(11) 0.0084(8) 0.0212(9) 0.0113(8) C15 0.0429(16) 0.0596(18) 0.072(2) 0.0067(15) 0.0243(15) 0.0192(13) C16 0.0398(13) 0.0328(12) 0.0421(14) 0.0001(10) 0.0208(11) 0.0026(10) C17 0.0531(16) 0.0505(15) 0.0438(15) 0.0011(12) 0.0244(13) -0.0032(13) C18 0.0569(17) 0.0637(18) 0.0430(15) -0.0048(14) 0.0190(14) -0.0026(14) C19 0.0431(15) 0.0547(17) 0.0636(19) -0.0133(14) 0.0207(14) -0.0022(13) C20 0.0456(16) 0.0408(15) 0.070(2) 0.0043(14) 0.0219(15) -0.0025(12) C21 0.0444(15) 0.0401(14) 0.0555(16) 0.0085(12) 0.0204(13) 0.0033(12) _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 C2 1.390(3) . ? C1 C12 1.427(3) . ? C1 C13 1.461(3) . ? C2 O1 1.348(3) . ? C2 C3 1.425(3) . ? O1 H1 0.8400 . ? C3 C4 1.411(3) . ? C3 C8 1.425(3) . ? C4 C5 1.368(3) . ? C4 H4 0.9500 . ? C5 C6 1.404(4) . ? C5 H5 0.9500 . ? C6 C7 1.371(3) . ? C6 H6 0.9500 . ? C7 C8 1.405(3) . ? C7 H7 0.9500 . ? C8 C9 1.412(3) . ? C9 C12 1.355(3) . ? C9 O2 1.381(3) . ? O2 C10 1.443(3) . ? C10 O5 1.391(3) . ? C10 C11 1.538(3) . ? C10 H10 1.0000 . ? C11 C12 1.519(3) . ? C11 C16 1.526(3) . ? C11 H11 1.0000 . ? C13 O3 1.228(3) . ? C13 O4 1.327(3) . ? O4 C14 1.433(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O5 C15 1.430(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.372(3) . ? C16 C21 1.383(3) . ? C17 C18 1.387(4) . ? C17 H17 0.9500 . ? C18 C19 1.378(4) . ? C18 H18 0.9500 . ? C19 C20 1.369(4) . ? C19 H19 0.9500 . ? C20 C21 1.384(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? 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 C2 C1 C12 118.1(2) . . ? C2 C1 C13 118.7(2) . . ? C12 C1 C13 123.2(2) . . ? O1 C2 C1 122.8(2) . . ? O1 C2 C3 115.6(2) . . ? C1 C2 C3 121.6(2) . . ? C2 O1 H1 109.5 . . ? C4 C3 C8 118.4(2) . . ? C4 C3 C2 121.8(2) . . ? C8 C3 C2 119.8(2) . . ? C5 C4 C3 120.7(2) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 120.1(2) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.6(2) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C9 124.1(2) . . ? C7 C8 C3 119.5(2) . . ? C9 C8 C3 116.3(2) . . ? C12 C9 O2 114.16(19) . . ? C12 C9 C8 124.1(2) . . ? O2 C9 C8 121.68(19) . . ? C9 O2 C10 106.11(16) . . ? O5 C10 O2 110.23(19) . . ? O5 C10 C11 108.20(18) . . ? O2 C10 C11 107.53(17) . . ? O5 C10 H10 110.3 . . ? O2 C10 H10 110.3 . . ? C11 C10 H10 110.3 . . ? C12 C11 C16 114.93(19) . . ? C12 C11 C10 100.67(17) . . ? C16 C11 C10 113.03(19) . . ? C12 C11 H11 109.3 . . ? C16 C11 H11 109.3 . . ? C10 C11 H11 109.3 . . ? C9 C12 C1 120.0(2) . . ? C9 C12 C11 108.31(19) . . ? C1 C12 C11 131.7(2) . . ? O3 C13 O4 121.7(2) . . ? O3 C13 C1 124.5(2) . . ? O4 C13 C1 113.79(19) . . ? C13 O4 C14 116.93(19) . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 O5 C15 113.16(19) . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 118.6(2) . . ? C17 C16 C11 121.7(2) . . ? C21 C16 C11 119.7(2) . . ? C16 C17 C18 120.9(2) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 119.9(3) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C20 C19 C18 119.9(3) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 119.9(3) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C16 C21 C20 120.9(2) . . ? C16 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? 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 C12 C1 C2 O1 178.0(2) . . . . ? C13 C1 C2 O1 -2.7(3) . . . . ? C12 C1 C2 C3 -0.7(3) . . . . ? C13 C1 C2 C3 178.5(2) . . . . ? O1 C2 C3 C4 2.3(3) . . . . ? C1 C2 C3 C4 -178.8(2) . . . . ? O1 C2 C3 C8 -178.2(2) . . . . ? C1 C2 C3 C8 0.7(3) . . . . ? C8 C3 C4 C5 -0.5(4) . . . . ? C2 C3 C4 C5 179.1(2) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? C4 C5 C6 C7 0.5(4) . . . . ? C5 C6 C7 C8 -1.1(4) . . . . ? C6 C7 C8 C9 -179.6(2) . . . . ? C6 C7 C8 C3 0.9(3) . . . . ? C4 C3 C8 C7 -0.1(3) . . . . ? C2 C3 C8 C7 -179.6(2) . . . . ? C4 C3 C8 C9 -179.6(2) . . . . ? C2 C3 C8 C9 0.8(3) . . . . ? C7 C8 C9 C12 178.0(2) . . . . ? C3 C8 C9 C12 -2.5(3) . . . . ? C7 C8 C9 O2 -0.9(4) . . . . ? C3 C8 C9 O2 178.6(2) . . . . ? C12 C9 O2 C10 10.8(3) . . . . ? C8 C9 O2 C10 -170.2(2) . . . . ? C9 O2 C10 O5 100.2(2) . . . . ? C9 O2 C10 C11 -17.5(2) . . . . ? O5 C10 C11 C12 -101.9(2) . . . . ? O2 C10 C11 C12 17.1(2) . . . . ? O5 C10 C11 C16 135.0(2) . . . . ? O2 C10 C11 C16 -106.0(2) . . . . ? O2 C9 C12 C1 -178.52(19) . . . . ? C8 C9 C12 C1 2.5(4) . . . . ? O2 C9 C12 C11 0.7(3) . . . . ? C8 C9 C12 C11 -178.3(2) . . . . ? C2 C1 C12 C9 -0.8(3) . . . . ? C13 C1 C12 C9 180.0(2) . . . . ? C2 C1 C12 C11 -179.8(2) . . . . ? C13 C1 C12 C11 1.0(4) . . . . ? C16 C11 C12 C9 110.9(2) . . . . ? C10 C11 C12 C9 -10.9(2) . . . . ? C16 C11 C12 C1 -70.1(3) . . . . ? C10 C11 C12 C1 168.2(2) . . . . ? C2 C1 C13 O3 -1.3(4) . . . . ? C12 C1 C13 O3 177.8(2) . . . . ? C2 C1 C13 O4 178.7(2) . . . . ? C12 C1 C13 O4 -2.1(3) . . . . ? O3 C13 O4 C14 -4.1(3) . . . . ? C1 C13 O4 C14 175.81(19) . . . . ? O2 C10 O5 C15 68.4(2) . . . . ? C11 C10 O5 C15 -174.3(2) . . . . ? C12 C11 C16 C17 -33.6(3) . . . . ? C10 C11 C16 C17 81.2(3) . . . . ? C12 C11 C16 C21 148.0(2) . . . . ? C10 C11 C16 C21 -97.2(3) . . . . ? C21 C16 C17 C18 -1.0(4) . . . . ? C11 C16 C17 C18 -179.4(2) . . . . ? C16 C17 C18 C19 0.4(4) . . . . ? C17 C18 C19 C20 0.5(4) . . . . ? C18 C19 C20 C21 -0.8(4) . . . . ? C17 C16 C21 C20 0.7(4) . . . . ? C11 C16 C21 C20 179.2(2) . . . . ? C19 C20 C21 C16 0.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.267 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 948264'