# Electronic Supplementary Material (ESI) for Chemical Science # 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_n0680_0m #TrackingRef 'web_deposit_cif_file_0_KarlScheidt_1360620968.RBFStructure1_MW_edit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 O3' _chemical_formula_sum 'C13 H14 O3' _chemical_formula_weight 218.24 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 Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.27380(10) _cell_length_b 11.20700(10) _cell_length_c 19.0373(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2191.93(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description tabular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9519 _exptl_absorpt_correction_T_max 0.9892 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43646 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 30.23 _reflns_number_total 3245 _reflns_number_gt 2664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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 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^)+(0.0578P)^2^+0.2704P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3245 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.04799(6) 0.49535(6) 0.32759(3) 0.02037(15) Uani 1 1 d . . . O3 O 0.16533(6) 0.27568(6) 0.62821(4) 0.02571(17) Uani 1 1 d . . . O2 O 0.25147(6) 0.44320(6) 0.54966(4) 0.02132(15) Uani 1 1 d . . . C1 C 0.15536(8) 0.46998(7) 0.43839(5) 0.01641(17) Uani 1 1 d . . . C2 C 0.16126(8) 0.40789(8) 0.50227(5) 0.01662(17) Uani 1 1 d . . . C3 C 0.07631(8) 0.31120(7) 0.51608(5) 0.01705(17) Uani 1 1 d . . . C4 C 0.06169(8) 0.43556(8) 0.38911(5) 0.01672(17) Uani 1 1 d . . . C5 C -0.02649(8) 0.34317(8) 0.40240(5) 0.01892(18) Uani 1 1 d . . . C6 C -0.01752(8) 0.28178(8) 0.46497(5) 0.01836(18) Uani 1 1 d . . . C7 C 0.08624(8) 0.24538(8) 0.58224(5) 0.01951(18) Uani 1 1 d . . . C8 C 0.23655(9) 0.61793(8) 0.35727(5) 0.02085(19) Uani 1 1 d . . . C9 C 0.16164(8) 0.55817(8) 0.29901(5) 0.01929(18) Uani 1 1 d . . . C10 C 0.00100(10) 0.13832(9) 0.59469(5) 0.0247(2) Uani 1 1 d . . . C11 C 0.23610(8) 0.57350(8) 0.42236(5) 0.01944(18) Uani 1 1 d . . . C12 C 0.10427(10) 0.64754(9) 0.24766(5) 0.0244(2) Uani 1 1 d . . . C13 C 0.24702(10) 0.46690(9) 0.26159(5) 0.0251(2) Uani 1 1 d . . . H1 H -0.0801(11) 0.2177(10) 0.4754(6) 0.019(3) Uiso 1 1 d . . . H4 H 0.2872(13) 0.6096(11) 0.4610(6) 0.028(3) Uiso 1 1 d . . . H8 H 0.1754(14) 0.6934(12) 0.2262(7) 0.039(4) Uiso 1 1 d . . . H9 H 0.0576(13) 0.6053(11) 0.2100(7) 0.031(3) Uiso 1 1 d . . . H3 H 0.2925(13) 0.6900(11) 0.3427(6) 0.028(3) Uiso 1 1 d . . . H2 H -0.0928(12) 0.3237(10) 0.3671(7) 0.027(3) Uiso 1 1 d . . . H5 H 0.1988(13) 0.4251(10) 0.2261(6) 0.028(3) Uiso 1 1 d . . . H7 H 0.2808(12) 0.4085(11) 0.2942(7) 0.029(3) Uiso 1 1 d . . . H10 H 0.0449(13) 0.7036(11) 0.2726(7) 0.032(3) Uiso 1 1 d . . . H6 H 0.3211(14) 0.5064(12) 0.2389(7) 0.033(3) Uiso 1 1 d . . . H11 H 0.2367(15) 0.3963(15) 0.5887(8) 0.053(5) Uiso 1 1 d . . . H14 H 0.0149(14) 0.1067(12) 0.6414(8) 0.042(4) Uiso 1 1 d . . . H12 H 0.0210(14) 0.0729(13) 0.5617(8) 0.044(4) Uiso 1 1 d . . . H13 H -0.0916(14) 0.1573(13) 0.5893(7) 0.039(4) Uiso 1 1 d . . . 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 0.0163(3) 0.0235(3) 0.0214(3) 0.0049(2) -0.0024(2) -0.0037(2) O3 0.0236(3) 0.0322(4) 0.0213(3) 0.0017(3) -0.0029(3) 0.0013(3) O2 0.0186(3) 0.0248(3) 0.0206(3) -0.0025(3) -0.0048(2) -0.0021(2) C1 0.0141(4) 0.0153(4) 0.0198(4) -0.0022(3) -0.0001(3) 0.0001(3) C2 0.0137(3) 0.0175(4) 0.0187(4) -0.0039(3) -0.0010(3) 0.0020(3) C3 0.0154(4) 0.0171(4) 0.0187(4) -0.0013(3) 0.0010(3) 0.0020(3) C4 0.0154(4) 0.0171(4) 0.0176(4) -0.0008(3) 0.0000(3) 0.0014(3) C5 0.0163(4) 0.0202(4) 0.0202(4) -0.0016(3) -0.0022(3) -0.0027(3) C6 0.0169(4) 0.0172(4) 0.0210(4) -0.0017(3) 0.0010(3) -0.0012(3) C7 0.0171(4) 0.0211(4) 0.0203(4) 0.0004(3) 0.0025(3) 0.0049(3) C8 0.0187(4) 0.0178(4) 0.0260(4) -0.0008(3) 0.0014(3) -0.0024(3) C9 0.0173(4) 0.0191(4) 0.0214(4) 0.0020(3) 0.0016(3) -0.0017(3) C10 0.0235(4) 0.0242(5) 0.0264(5) 0.0057(4) 0.0022(4) 0.0006(4) C11 0.0172(4) 0.0171(4) 0.0241(4) -0.0036(3) -0.0010(3) -0.0022(3) C12 0.0257(4) 0.0240(5) 0.0236(4) 0.0055(4) 0.0013(4) 0.0001(4) C13 0.0215(4) 0.0271(5) 0.0269(5) -0.0048(4) 0.0002(4) 0.0017(4) _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 C4 1.3566(10) . ? O1 C9 1.4681(10) . ? O3 C7 1.2415(11) . ? O2 C2 1.3525(10) . ? C1 C4 1.3983(12) . ? C1 C2 1.4025(12) . ? C1 C11 1.4584(12) . ? C2 C3 1.4160(12) . ? C3 C6 1.4088(12) . ? C3 C7 1.4632(12) . ? C4 C5 1.3989(12) . ? C5 C6 1.3786(12) . ? C7 C10 1.5041(13) . ? C8 C11 1.3354(13) . ? C8 C9 1.5070(13) . ? C9 C12 1.5185(13) . ? C9 C13 1.5243(13) . ? 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 C4 O1 C9 118.32(6) . . ? C4 C1 C2 118.33(7) . . ? C4 C1 C11 118.07(8) . . ? C2 C1 C11 123.47(8) . . ? O2 C2 C1 117.57(8) . . ? O2 C2 C3 121.50(8) . . ? C1 C2 C3 120.93(7) . . ? C6 C3 C2 118.20(8) . . ? C6 C3 C7 121.62(8) . . ? C2 C3 C7 120.17(8) . . ? O1 C4 C1 120.95(7) . . ? O1 C4 C5 117.04(7) . . ? C1 C4 C5 121.91(8) . . ? C6 C5 C4 118.84(8) . . ? C5 C6 C3 121.72(8) . . ? O3 C7 C3 120.97(8) . . ? O3 C7 C10 119.22(8) . . ? C3 C7 C10 119.81(8) . . ? C11 C8 C9 121.03(8) . . ? O1 C9 C8 110.27(7) . . ? O1 C9 C12 104.26(7) . . ? C8 C9 C12 112.27(8) . . ? O1 C9 C13 108.00(7) . . ? C8 C9 C13 110.38(7) . . ? C12 C9 C13 111.42(8) . . ? C8 C11 C1 119.52(8) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.23 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.413 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 924171'