# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full MedChemComm _journal_coden_cambridge 1476 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email thomas.webb@stjude.org _publ_contact_author_name 'Thomas Webb' loop_ _publ_author_name 'Mahesh Gundluru' 'Alan Pourpak' 'Xiaoli Cui' 'Stephan Morris' 'Thomas Webb' data_sj10_003 _database_code_depnum_ccdc_archive 'CCDC 805182' #TrackingRef 'Compound-16.cif' _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C10 H14 O3' _chemical_formula_sum 'C10 H14 O3' _chemical_formula_weight 182.21 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 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 9.4612(5) _cell_length_b 13.0067(6) _cell_length_c 14.8753(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1830.54(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9856 _cell_measurement_theta_min 6.50 _cell_measurement_theta_max 65.67 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.000 -1.000 -2.000 0.02300 0.000 1.000 2.000 0.04200 2.000 1.000 2.000 0.11200 -2.000 -1.000 -2.000 0.08500 0.000 -2.000 -1.000 0.02200 0.000 2.000 1.000 0.03200 0.000 -1.000 1.000 0.03700 0.000 1.000 -1.000 0.01700 2.000 0.000 -1.000 0.12000 -2.000 0.000 1.000 0.12000 _exptl_absorpt_coefficient_mu 0.795 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7571 _exptl_absorpt_correction_T_max 0.9182 _exptl_absorpt_process_details 'SADABS 2008/1 (Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source 'rotating-anode x-ray generator' _diffrn_source_type FR-591 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_collimation 'focusing mirrors' _diffrn_measurement_device 'four-circle kappa goniometer' _diffrn_measurement_device_type 'Bruker X8 Kappa' _diffrn_measurement_method '\w scans' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker Platinum-135' _diffrn_detector_area_resol_mean 10.73 _diffrn_reflns_number 28866 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.95 _diffrn_reflns_theta_full 63.00 _diffrn_reflns_theta_max 66.12 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.961 _reflns_number_total 1532 _reflns_number_gt 1474 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Apex2 (Bruker, 2009)' _computing_cell_refinement 'Apex2 (Bruker, 2009)' _computing_data_reduction 'SAINT 7.68A (Bruker, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Platon (Spek, 2010)' _computing_publication_material ? _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ' w=[\s^2^(Fo^2^)+(0.0300P)^2^+0.7500P]^-1^ where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1532 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0680 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.118 _refine_ls_shift/su_mean 0.019 _refine_diff_density_max 0.231 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.030 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 0.04824(7) 0.63172(6) 0.14665(5) 0.0184(2) Uani 1 1 d . . . C2 C -0.00476(11) 0.66610(8) 0.06893(7) 0.0181(2) Uani 1 1 d . . . O3 O -0.13275(8) 0.67556(6) 0.06515(5) 0.0234(2) Uani 1 1 d . . . C4 C 0.08785(12) 0.69325(9) -0.00984(8) 0.0219(3) Uani 1 1 d . . . H4A H 0.0236(14) 0.7218(10) -0.0550(9) 0.024(3) Uiso 1 1 d . . . H4B H 0.1535(14) 0.7466(10) 0.0087(8) 0.021(3) Uiso 1 1 d . . . C5 C 0.16959(12) 0.60338(10) -0.05149(8) 0.0233(3) Uani 1 1 d . . . H5A H 0.1042(14) 0.5467(11) -0.0636(9) 0.027(3) Uiso 1 1 d . . . H5B H 0.2049(14) 0.6283(10) -0.1103(10) 0.028(3) Uiso 1 1 d . . . C6 C 0.29345(12) 0.56406(9) 0.00396(8) 0.0224(3) Uani 1 1 d . . . H6A H 0.3637(13) 0.6195(10) 0.0093(8) 0.019(3) Uiso 1 1 d . . . H6B H 0.3390(13) 0.5074(11) -0.0279(9) 0.023(3) Uiso 1 1 d . . . C7 C 0.25206(12) 0.52488(9) 0.09693(7) 0.0202(3) Uani 1 1 d . . . H7A H 0.1815(13) 0.4700(10) 0.0922(8) 0.018(3) Uiso 1 1 d . . . H7B H 0.3367(14) 0.4937(10) 0.1252(9) 0.025(3) Uiso 1 1 d . . . C8 C 0.19784(11) 0.60466(8) 0.16370(7) 0.0182(3) Uani 1 1 d . . . C9 C 0.28879(12) 0.70011(9) 0.17042(8) 0.0225(3) Uani 1 1 d . . . H9A H 0.2930(13) 0.7387(11) 0.1128(9) 0.027(3) Uiso 1 1 d . . . H9B H 0.3851(15) 0.6794(10) 0.1860(9) 0.027(3) Uiso 1 1 d . . . H9C H 0.2528(15) 0.7456(11) 0.2178(9) 0.030(3) Uiso 1 1 d . . . C10 C 0.18946(12) 0.55542(9) 0.25828(7) 0.0196(3) Uani 1 1 d . . . H10 H 0.2848(13) 0.5339(9) 0.2724(8) 0.014(3) Uiso 1 1 d . . . O11 O 0.14039(9) 0.62685(6) 0.32365(5) 0.0247(2) Uani 1 1 d . . . H11 H 0.2153(19) 0.6446(13) 0.3553(12) 0.051(5) Uiso 1 1 d . . . C12 C 0.09817(12) 0.46371(9) 0.25982(7) 0.0212(3) Uani 1 1 d . . . C13 C 0.02781(13) 0.38813(10) 0.26171(8) 0.0265(3) Uani 1 1 d . . . H13 H -0.0290(16) 0.3275(12) 0.2620(10) 0.041(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 0.0138(4) 0.0244(4) 0.0170(4) 0.0025(3) -0.0007(3) 0.0016(3) C2 0.0181(6) 0.0179(5) 0.0184(6) 0.0014(4) -0.0015(4) 0.0008(4) O3 0.0150(4) 0.0328(5) 0.0223(4) 0.0071(3) -0.0002(3) 0.0028(3) C4 0.0178(6) 0.0280(6) 0.0199(6) 0.0061(5) -0.0001(5) 0.0006(5) C5 0.0218(6) 0.0315(6) 0.0167(6) 0.0012(5) 0.0017(5) -0.0006(5) C6 0.0201(6) 0.0267(6) 0.0203(6) -0.0028(5) 0.0029(4) 0.0023(5) C7 0.0192(5) 0.0224(6) 0.0191(6) -0.0011(4) -0.0012(5) 0.0024(5) C8 0.0121(5) 0.0234(6) 0.0191(6) -0.0004(4) -0.0024(4) 0.0026(4) C9 0.0169(6) 0.0246(6) 0.0260(6) -0.0034(5) -0.0006(5) -0.0006(5) C10 0.0162(6) 0.0255(6) 0.0173(6) -0.0020(4) -0.0020(4) 0.0050(4) O11 0.0208(4) 0.0339(5) 0.0193(4) -0.0082(3) -0.0025(3) 0.0046(3) C12 0.0200(5) 0.0278(6) 0.0157(6) 0.0026(4) 0.0001(4) 0.0074(5) C13 0.0256(6) 0.0271(6) 0.0268(7) 0.0034(5) 0.0037(5) 0.0032(5) _geom_special_details ; All esds 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. ; 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 C2 1.3371(13) . ? O1 C8 1.4804(12) . ? C2 O3 1.2185(14) . ? C2 C4 1.5052(15) . ? C4 C5 1.5324(16) . ? C5 C6 1.5215(16) . ? C6 C7 1.5250(16) . ? C7 C8 1.5253(15) . ? C8 C9 1.5139(16) . ? C8 C10 1.5478(15) . ? C10 O11 1.4227(13) . ? C10 C12 1.4729(16) . ? C12 C13 1.1876(18) . ? C4 H4A 0.979(14) . ? C4 H4B 0.971(14) . ? C5 H5A 0.979(14) . ? C5 H5B 0.991(14) . ? C6 H6A 0.984(13) . ? C6 H6B 0.977(14) . ? C7 H7A 0.980(13) . ? C7 H7B 0.991(14) . ? C9 H9A 0.994(14) . ? C9 H9B 0.978(14) . ? C9 H9C 0.982(15) . ? C10 H10 0.968(12) . ? O11 H11 0.882(19) . ? C13 H13 0.954(16) . ? 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 O1 C8 125.89(8) . . ? O3 C2 O1 116.51(9) . . ? O3 C2 C4 121.26(10) . . ? O1 C2 C4 122.22(9) . . ? C2 C4 C5 115.44(10) . . ? C6 C5 C4 115.21(10) . . ? C5 C6 C7 113.96(9) . . ? C6 C7 C8 116.72(9) . . ? O1 C8 C9 111.08(9) . . ? O1 C8 C7 111.82(9) . . ? C9 C8 C7 114.19(9) . . ? O1 C8 C10 101.84(8) . . ? C9 C8 C10 107.96(9) . . ? C7 C8 C10 109.13(9) . . ? O11 C10 C12 109.08(9) . . ? O11 C10 C8 111.58(9) . . ? C12 C10 C8 112.29(9) . . ? C13 C12 C10 178.14(12) . . ? C2 C4 H4A 105.2(7) . . ? C5 C4 H4A 109.0(7) . . ? C2 C4 H4B 108.6(7) . . ? C5 C4 H4B 109.7(7) . . ? H4A C4 H4B 108.7(11) . . ? C6 C5 H5A 109.5(8) . . ? C4 C5 H5A 109.3(8) . . ? C6 C5 H5B 109.2(8) . . ? C4 C5 H5B 106.1(8) . . ? H5A C5 H5B 107.2(11) . . ? C5 C6 H6A 108.5(7) . . ? C7 C6 H6A 110.2(7) . . ? C5 C6 H6B 109.3(7) . . ? C7 C6 H6B 107.6(8) . . ? H6A C6 H6B 107.1(10) . . ? C6 C7 H7A 110.7(7) . . ? C8 C7 H7A 108.3(7) . . ? C6 C7 H7B 108.3(8) . . ? C8 C7 H7B 105.9(8) . . ? H7A C7 H7B 106.4(10) . . ? C8 C9 H9A 112.3(8) . . ? C8 C9 H9B 108.6(8) . . ? H9A C9 H9B 107.8(11) . . ? C8 C9 H9C 110.2(8) . . ? H9A C9 H9C 109.2(11) . . ? H9B C9 H9C 108.6(11) . . ? O11 C10 H10 110.2(7) . . ? C12 C10 H10 108.0(7) . . ? C8 C10 H10 105.6(7) . . ? C10 O11 H11 105.9(11) . . ? C12 C13 H13 178.9(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 C8 O1 C2 O3 173.58(9) . . . . ? C8 O1 C2 C4 -7.18(16) . . . . ? O3 C2 C4 C5 -115.89(12) . . . . ? O1 C2 C4 C5 64.91(14) . . . . ? C2 C4 C5 C6 -73.25(13) . . . . ? C4 C5 C6 C7 59.92(14) . . . . ? C5 C6 C7 C8 -67.12(13) . . . . ? C2 O1 C8 C9 73.48(13) . . . . ? C2 O1 C8 C7 -55.38(13) . . . . ? C2 O1 C8 C10 -171.78(9) . . . . ? C6 C7 C8 O1 79.12(12) . . . . ? C6 C7 C8 C9 -48.08(13) . . . . ? C6 C7 C8 C10 -168.99(9) . . . . ? O1 C8 C10 O11 -62.12(10) . . . . ? C9 C8 C10 O11 54.90(12) . . . . ? C7 C8 C10 O11 179.54(9) . . . . ? O1 C8 C10 C12 60.70(10) . . . . ? C9 C8 C10 C12 177.72(9) . . . . ? C7 C8 C10 C12 -57.64(12) . . . . ? O11 C10 C12 C13 -119(4) . . . . ? C8 C10 C12 C13 117(4) . . . . ? 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 O11 H11 O3 0.882(19) 1.905(19) 2.7829(11) 173.6(16) 6_656