# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Kenneth Hardcastle' _publ_contact_author_email khardca@emory.edu loop_ _publ_author_name 'Daniel Morton' 'Allison R. Dick' 'Debashis Ghosh' 'Huw M. L. Davies' data_dmr251 _database_code_depnum_ccdc_archive 'CCDC 829542' #TrackingRef 'DMR251.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H32 O3' _chemical_formula_sum 'C23 H32 O3' _chemical_formula_weight 356.49 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 P2(1)2(1)2(1) _chemical_absolute_configuration ad 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' _cell_length_a 11.061(4) _cell_length_b 11.333(4) _cell_length_c 16.323(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2046.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 685 _cell_measurement_theta_min 6.74 _cell_measurement_theta_max 33.02 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.587 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7907 _exptl_absorpt_correction_T_max 0.9657 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8524 _diffrn_reflns_av_R_equivalents 0.1431 _diffrn_reflns_av_sigmaI/netI 0.1772 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.83 _diffrn_reflns_theta_max 66.59 _reflns_number_total 3211 _reflns_number_gt 936 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0310P)^2^+1.9000P] 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 SHELXL _refine_ls_extinction_coef 0.0131(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(9) _refine_ls_number_reflns 3211 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2368 _refine_ls_R_factor_gt 0.0810 _refine_ls_wR_factor_ref 0.1970 _refine_ls_wR_factor_gt 0.1480 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 C1 C 0.5192(9) 0.0574(13) -0.0009(9) 0.115(4) Uani 1 1 d . . . C2 C 0.4757(8) 0.0860(11) -0.0796(7) 0.101(3) Uani 1 1 d . . . H2 H 0.4666 0.0262 -0.1199 0.121 Uiso 1 1 calc R . . C3 C 0.4467(9) 0.1995(11) -0.0972(6) 0.098(3) Uani 1 1 d . . . H3A H 0.4166 0.2176 -0.1502 0.117 Uiso 1 1 calc R . . C4 C 0.4605(8) 0.2980(10) -0.0358(6) 0.085(3) Uani 1 1 d . . . C5 C 0.5533(8) 0.3879(8) -0.0721(6) 0.081(3) Uani 1 1 d . . . H5A H 0.6324 0.3461 -0.0785 0.098 Uiso 1 1 calc R . . C6 C 0.5168(8) 0.4364(8) -0.1560(5) 0.096(3) Uani 1 1 d . . . H6A H 0.4358 0.4731 -0.1516 0.115 Uiso 1 1 calc R . . H6B H 0.5107 0.3701 -0.1953 0.115 Uiso 1 1 calc R . . C7 C 0.6076(9) 0.5297(8) -0.1905(5) 0.098(3) Uani 1 1 d . . . H7A H 0.6869 0.4922 -0.2013 0.118 Uiso 1 1 calc R . . H7B H 0.5767 0.5627 -0.2426 0.118 Uiso 1 1 calc R . . C8 C 0.6214(9) 0.6268(9) -0.1277(7) 0.092(3) Uani 1 1 d . . . C9 C 0.7192(11) 0.7127(11) -0.1469(8) 0.113(4) Uani 1 1 d . . . C10 C 0.7771(8) 0.7565(8) -0.0689(6) 0.107(3) Uani 1 1 d . . . H10A H 0.7638 0.8423 -0.0619 0.129 Uiso 1 1 calc R . . H10B H 0.8651 0.7406 -0.0689 0.129 Uiso 1 1 calc R . . C11 C 0.7120(8) 0.6846(8) 0.0005(6) 0.097(3) Uani 1 1 d . . . H11A H 0.6436 0.7294 0.0243 0.116 Uiso 1 1 calc R . . H11B H 0.7688 0.6622 0.0447 0.116 Uiso 1 1 calc R . . C12 C 0.6668(8) 0.5737(8) -0.0484(5) 0.080(3) Uani 1 1 d . . . H12A H 0.7395 0.5249 -0.0618 0.095 Uiso 1 1 calc R . . C13 C 0.5723(8) 0.4913(8) -0.0112(6) 0.081(3) Uani 1 1 d . . . H13A H 0.4946 0.5346 -0.0026 0.098 Uiso 1 1 calc R . . C14 C 0.6188(7) 0.4403(8) 0.0714(5) 0.084(3) Uani 1 1 d . . . H14A H 0.7001 0.4061 0.0627 0.101 Uiso 1 1 calc R . . H14B H 0.6270 0.5056 0.1113 0.101 Uiso 1 1 calc R . . C15 C 0.5356(9) 0.3448(9) 0.1083(6) 0.091(3) Uani 1 1 d . . . H15A H 0.5752 0.3063 0.1565 0.109 Uiso 1 1 calc R . . C16 C 0.5061(8) 0.2554(13) 0.0442(6) 0.088(3) Uani 1 1 d . . . C17 C 0.5363(9) 0.1445(13) 0.0634(7) 0.097(3) Uani 1 1 d . . . H17 H 0.5670 0.1239 0.1159 0.117 Uiso 1 1 calc R . . C18 C 0.5069(8) 0.7037(8) -0.1198(5) 0.110(4) Uani 1 1 d . . . H18A H 0.4834 0.7329 -0.1740 0.165 Uiso 1 1 calc R . . H18B H 0.5235 0.7707 -0.0836 0.165 Uiso 1 1 calc R . . H18C H 0.4409 0.6564 -0.0969 0.165 Uiso 1 1 calc R . . C19 C 0.3341(7) 0.3514(8) -0.0285(5) 0.107(4) Uani 1 1 d . . . H19A H 0.2790 0.2931 -0.0046 0.160 Uiso 1 1 calc R . . H19B H 0.3051 0.3741 -0.0830 0.160 Uiso 1 1 calc R . . H19C H 0.3373 0.4213 0.0068 0.160 Uiso 1 1 calc R . . C20 C 0.3828(11) 0.3782(10) 0.2145(8) 0.110(3) Uani 1 1 d . . . C21 C 0.3573(10) 0.2459(8) 0.2242(6) 0.156(5) Uani 1 1 d . . . H21A H 0.2940 0.2222 0.1855 0.234 Uiso 1 1 calc R . . H21B H 0.3302 0.2298 0.2803 0.234 Uiso 1 1 calc R . . H21C H 0.4312 0.2011 0.2130 0.234 Uiso 1 1 calc R . . C22 C 0.4752(11) 0.4191(13) 0.2752(7) 0.183(6) Uani 1 1 d . . . H22A H 0.4869 0.5044 0.2696 0.274 Uiso 1 1 calc R . . H22B H 0.5520 0.3784 0.2650 0.274 Uiso 1 1 calc R . . H22C H 0.4473 0.4011 0.3308 0.274 Uiso 1 1 calc R . . C23 C 0.2690(11) 0.4472(10) 0.2227(8) 0.206(7) Uani 1 1 d . . . H23A H 0.2869 0.5316 0.2178 0.309 Uiso 1 1 calc R . . H23B H 0.2325 0.4316 0.2764 0.309 Uiso 1 1 calc R . . H23C H 0.2124 0.4239 0.1794 0.309 Uiso 1 1 calc R . . O1 O 0.5507(7) -0.0495(7) 0.0138(4) 0.118(2) Uani 1 1 d . . . O2 O 0.7503(7) 0.7477(6) -0.2161(5) 0.124(3) Uani 1 1 d . . . O3 O 0.4277(6) 0.4053(5) 0.1330(4) 0.095(2) Uani 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 C1 0.086(8) 0.133(12) 0.126(11) 0.040(11) -0.006(8) 0.025(8) C2 0.108(8) 0.103(10) 0.091(8) 0.009(8) -0.016(7) -0.008(7) C3 0.114(8) 0.103(9) 0.076(7) 0.005(7) -0.011(6) 0.003(8) C4 0.060(6) 0.106(8) 0.090(8) -0.007(7) 0.001(6) 0.008(6) C5 0.079(6) 0.077(7) 0.088(7) -0.016(6) -0.007(6) 0.008(5) C6 0.123(8) 0.084(7) 0.080(7) 0.010(6) -0.017(6) -0.006(7) C7 0.132(9) 0.093(8) 0.069(7) -0.014(6) 0.008(6) -0.007(7) C8 0.094(8) 0.087(8) 0.094(9) -0.005(7) 0.008(7) 0.000(7) C9 0.120(10) 0.119(11) 0.100(10) 0.000(9) -0.004(9) 0.008(9) C10 0.108(8) 0.114(9) 0.100(8) 0.004(7) 0.007(7) -0.032(7) C11 0.108(7) 0.105(8) 0.077(7) -0.010(7) -0.005(6) -0.015(7) C12 0.071(6) 0.089(7) 0.079(7) 0.004(6) 0.000(5) -0.002(6) C13 0.064(6) 0.097(7) 0.083(7) -0.007(6) 0.001(5) 0.020(6) C14 0.089(6) 0.072(6) 0.091(7) -0.015(6) -0.011(6) 0.003(6) C15 0.076(7) 0.092(8) 0.105(8) 0.008(7) 0.009(6) 0.001(6) C16 0.063(6) 0.117(10) 0.082(9) 0.005(8) -0.005(6) 0.002(6) C17 0.092(7) 0.120(10) 0.080(8) -0.021(8) 0.001(6) -0.014(7) C18 0.101(8) 0.093(8) 0.136(9) 0.033(7) -0.010(6) 0.016(6) C19 0.073(6) 0.126(9) 0.122(9) 0.023(7) 0.009(6) 0.011(6) C20 0.122(9) 0.086(9) 0.123(10) 0.015(8) -0.010(9) 0.008(8) C21 0.225(13) 0.076(8) 0.166(11) 0.014(8) 0.081(10) -0.025(9) C22 0.175(12) 0.251(16) 0.122(10) -0.038(11) -0.003(10) -0.010(13) C23 0.214(14) 0.168(13) 0.235(16) 0.056(11) 0.132(12) 0.104(12) O1 0.164(6) 0.110(6) 0.079(5) -0.008(5) 0.005(5) 0.013(6) O2 0.165(7) 0.085(6) 0.122(6) 0.010(5) 0.004(6) -0.015(5) O3 0.105(5) 0.095(5) 0.086(5) 0.010(4) 0.016(4) 0.011(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 C1 O1 1.283(12) . ? C1 C2 1.409(13) . ? C1 C17 1.454(14) . ? C2 C3 1.357(11) . ? C3 C4 1.508(12) . ? C4 C16 1.481(11) . ? C4 C19 1.528(10) . ? C4 C5 1.562(11) . ? C5 C6 1.531(9) . ? C5 C13 1.551(9) . ? C6 C7 1.563(10) . ? C7 C8 1.512(11) . ? C8 C9 1.488(13) . ? C8 C12 1.513(11) . ? C8 C18 1.544(10) . ? C9 O2 1.246(11) . ? C9 C10 1.509(11) . ? C10 C11 1.570(10) . ? C11 C12 1.570(10) . ? C12 C13 1.527(10) . ? C13 C14 1.554(10) . ? C14 C15 1.543(10) . ? C15 O3 1.435(9) . ? C15 C16 1.492(12) . ? C16 C17 1.337(12) . ? C20 O3 1.453(12) . ? C20 C23 1.488(12) . ? C20 C22 1.496(12) . ? C20 C21 1.535(12) . ? 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 O1 C1 C2 118.7(14) . . ? O1 C1 C17 118.1(13) . . ? C2 C1 C17 123.1(12) . . ? C3 C2 C1 119.5(11) . . ? C2 C3 C4 122.5(9) . . ? C16 C4 C3 112.2(9) . . ? C16 C4 C19 111.9(8) . . ? C3 C4 C19 104.6(8) . . ? C16 C4 C5 108.9(8) . . ? C3 C4 C5 107.3(8) . . ? C19 C4 C5 111.9(8) . . ? C6 C5 C13 109.7(8) . . ? C6 C5 C4 113.6(8) . . ? C13 C5 C4 109.8(8) . . ? C5 C6 C7 113.3(8) . . ? C8 C7 C6 108.2(8) . . ? C9 C8 C7 114.0(9) . . ? C9 C8 C12 101.5(9) . . ? C7 C8 C12 109.0(8) . . ? C9 C8 C18 104.1(8) . . ? C7 C8 C18 112.6(9) . . ? C12 C8 C18 115.2(8) . . ? O2 C9 C8 126.9(12) . . ? O2 C9 C10 122.9(12) . . ? C8 C9 C10 110.2(10) . . ? C9 C10 C11 104.1(9) . . ? C10 C11 C12 101.2(7) . . ? C8 C12 C13 110.8(8) . . ? C8 C12 C11 102.8(7) . . ? C13 C12 C11 120.3(8) . . ? C12 C13 C5 107.5(7) . . ? C12 C13 C14 110.2(7) . . ? C5 C13 C14 108.6(7) . . ? C15 C14 C13 113.7(7) . . ? O3 C15 C16 109.9(8) . . ? O3 C15 C14 105.7(8) . . ? C16 C15 C14 109.5(9) . . ? C17 C16 C4 126.8(11) . . ? C17 C16 C15 114.8(10) . . ? C4 C16 C15 118.1(11) . . ? C16 C17 C1 115.8(11) . . ? O3 C20 C23 105.1(9) . . ? O3 C20 C22 107.9(9) . . ? C23 C20 C22 110.9(11) . . ? O3 C20 C21 111.3(10) . . ? C23 C20 C21 110.4(11) . . ? C22 C20 C21 111.1(11) . . ? C15 O3 C20 116.1(7) . . ? 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 O1 C1 C2 C3 -177.3(10) . . . . ? C17 C1 C2 C3 -0.6(16) . . . . ? C1 C2 C3 C4 0.7(15) . . . . ? C2 C3 C4 C16 -1.1(14) . . . . ? C2 C3 C4 C19 -122.6(10) . . . . ? C2 C3 C4 C5 118.4(10) . . . . ? C16 C4 C5 C6 178.9(9) . . . . ? C3 C4 C5 C6 57.2(10) . . . . ? C19 C4 C5 C6 -57.0(10) . . . . ? C16 C4 C5 C13 -57.9(10) . . . . ? C3 C4 C5 C13 -179.6(8) . . . . ? C19 C4 C5 C13 66.2(10) . . . . ? C13 C5 C6 C7 54.6(10) . . . . ? C4 C5 C6 C7 177.9(7) . . . . ? C5 C6 C7 C8 -55.3(10) . . . . ? C6 C7 C8 C9 171.4(8) . . . . ? C6 C7 C8 C12 58.8(10) . . . . ? C6 C7 C8 C18 -70.3(10) . . . . ? C7 C8 C9 O2 34.9(16) . . . . ? C12 C8 C9 O2 151.8(11) . . . . ? C18 C8 C9 O2 -88.2(14) . . . . ? C7 C8 C9 C10 -146.4(9) . . . . ? C12 C8 C9 C10 -29.4(11) . . . . ? C18 C8 C9 C10 90.5(10) . . . . ? O2 C9 C10 C11 -178.0(10) . . . . ? C8 C9 C10 C11 3.2(11) . . . . ? C9 C10 C11 C12 23.3(9) . . . . ? C9 C8 C12 C13 173.5(8) . . . . ? C7 C8 C12 C13 -66.0(10) . . . . ? C18 C8 C12 C13 61.7(11) . . . . ? C9 C8 C12 C11 43.6(9) . . . . ? C7 C8 C12 C11 164.2(8) . . . . ? C18 C8 C12 C11 -68.2(10) . . . . ? C10 C11 C12 C8 -41.7(9) . . . . ? C10 C11 C12 C13 -165.5(7) . . . . ? C8 C12 C13 C5 63.4(9) . . . . ? C11 C12 C13 C5 -176.7(7) . . . . ? C8 C12 C13 C14 -178.4(7) . . . . ? C11 C12 C13 C14 -58.6(10) . . . . ? C6 C5 C13 C12 -56.5(9) . . . . ? C4 C5 C13 C12 178.0(7) . . . . ? C6 C5 C13 C14 -175.7(7) . . . . ? C4 C5 C13 C14 58.8(9) . . . . ? C12 C13 C14 C15 -173.1(7) . . . . ? C5 C13 C14 C15 -55.7(10) . . . . ? C13 C14 C15 O3 -68.8(9) . . . . ? C13 C14 C15 C16 49.4(10) . . . . ? C3 C4 C16 C17 1.6(15) . . . . ? C19 C4 C16 C17 118.9(11) . . . . ? C5 C4 C16 C17 -117.0(11) . . . . ? C3 C4 C16 C15 174.2(8) . . . . ? C19 C4 C16 C15 -68.6(12) . . . . ? C5 C4 C16 C15 55.6(11) . . . . ? O3 C15 C16 C17 -121.7(9) . . . . ? C14 C15 C16 C17 122.7(9) . . . . ? O3 C15 C16 C4 64.9(11) . . . . ? C14 C15 C16 C4 -50.7(11) . . . . ? C4 C16 C17 C1 -1.6(16) . . . . ? C15 C16 C17 C1 -174.3(8) . . . . ? O1 C1 C17 C16 177.7(10) . . . . ? C2 C1 C17 C16 1.0(15) . . . . ? C16 C15 O3 C20 108.9(10) . . . . ? C14 C15 O3 C20 -133.1(8) . . . . ? C23 C20 O3 C15 -177.3(9) . . . . ? C22 C20 O3 C15 64.4(11) . . . . ? C21 C20 O3 C15 -57.8(12) . . . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.289 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.063