data_g24fasm _audit_creation_method SHELXL-97 _audit_update_record ; 2005-04-04 text and data added, roy 2006-12-19 text and data added, srw ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H32 O2' _chemical_formula_sum 'C21 H32 O2' _chemical_formula_structural ? _chemical_formula_weight 316.47 _chemical_absolute_configuration syn _chemical_formula_analytical ? _chemical_compound_source ? 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 0.0000 '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 0.0000 '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 21 21 21 ' _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' _cell_length_a 7.430(2) _cell_length_b 8.883(2) _cell_length_c 26.604(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1755.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 916 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 28.28 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_crystal_id g24fasm _exptl_crystal_preparation ; The data crystal was mounted using oil (Parantone-N, Exxon) to a 0.3 mm cryo-loop (Hampton Research) with the (0 1 -3) scattering planes roughly normal to the spindle axis. ; _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.9629 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details 'SHELXTL/XPREP (Bruker, 2001)' _exptl_special_details ; One distinct cell was identified using SMART (Bruker, 2001). Four frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2001) then corrected for absorption by integration using SHELXTL/XPREP (Bruker, 2001) before using SAINT/SADABS (Bruker, 2001) to sort, merge, and scale the combined data. A series of identical frames was collected twice during the experiment to monitor and correct for decay. ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id g24fasm _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type ? _diffrn_measurement_device 'Siemens Platform/CCD' _diffrn_measurement_method 'profile data from \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 298 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 306 _diffrn_standards_decay_% 15.9 _diffrn_reflns_number 11593 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.37 _reflns_number_total 1875 _reflns_number_gt 1530 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT V6.22 (Bruker, 2001)' _computing_structure_solution 'SHELXTL V6.12 (Bruker, 2001)' _computing_structure_refinement 'SHELXTL V6.12 (Bruker, 2001)' _computing_molecular_graphics 'SHELXTL V6.12 (Bruker, 2001)' _computing_publication_material 'XCIF (Bruker, 2001)' _refine_special_details ; Structure was phased by direct methods. Systematic conditions suggested the unambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F^2^. The highest peaks in the final difference Fourier map were in the vicinity of atoms C17, C21, and C19; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed no dependence on amplitude or resolution. ; _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^)+(0.1049P)^2^+0.0934P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.010(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack (1983), 1325 Friedels' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 1875 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1401 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 -0.1420(4) 0.1307(3) 0.17112(11) 0.0383(7) Uani 1 1 d . . . H1A H -0.1824 0.2156 0.1924 0.046 Uiso 1 1 calc R . . H1B H -0.2419 0.1050 0.1480 0.046 Uiso 1 1 calc R . . O1 O 0.2481(3) -0.1995(2) 0.18955(8) 0.0533(6) Uani 1 1 d . . . O2 O 0.4424(3) -0.0418(2) 0.15314(7) 0.0411(5) Uani 1 1 d . . . C2 C -0.1043(4) -0.0044(3) 0.20473(12) 0.0453(8) Uani 1 1 d . . . H2A H -0.0806 -0.0940 0.1836 0.054 Uiso 1 1 calc R . . H2B H -0.2112 -0.0255 0.2258 0.054 Uiso 1 1 calc R . . C3 C 0.0576(4) 0.0256(4) 0.23847(11) 0.0426(7) Uani 1 1 d . . . H3A H 0.0816 -0.0654 0.2589 0.051 Uiso 1 1 calc R . . H3B H 0.0278 0.1086 0.2618 0.051 Uiso 1 1 calc R . . C4 C 0.2290(4) 0.0670(3) 0.20950(10) 0.0347(6) Uani 1 1 d . . . C5 C 0.1855(4) 0.2046(3) 0.17502(9) 0.0305(6) Uani 1 1 d . . . H5A H 0.1456 0.2847 0.1990 0.037 Uiso 1 1 calc R . . C6 C 0.3440(4) 0.2763(3) 0.14673(11) 0.0373(7) Uani 1 1 d . . . H6A H 0.4499 0.2831 0.1692 0.045 Uiso 1 1 calc R . . H6B H 0.3769 0.2132 0.1175 0.045 Uiso 1 1 calc R . . C7 C 0.2904(4) 0.4337(3) 0.12891(11) 0.0384(7) Uani 1 1 d . . . H7A H 0.2658 0.4974 0.1587 0.046 Uiso 1 1 calc R . . H7B H 0.3930 0.4789 0.1106 0.046 Uiso 1 1 calc R . . C8 C 0.1251(4) 0.4350(3) 0.09474(10) 0.0323(6) Uani 1 1 d . . . C9 C -0.0285(4) 0.3410(3) 0.11817(10) 0.0316(6) Uani 1 1 d . . . H9A H -0.0678 0.4003 0.1482 0.038 Uiso 1 1 calc R . . C10 C 0.0213(4) 0.1827(3) 0.13955(9) 0.0317(6) Uani 1 1 d . . . C11 C -0.1948(4) 0.3412(4) 0.08257(10) 0.0406(7) Uani 1 1 d . . . H11A H -0.2151 0.2376 0.0701 0.049 Uiso 1 1 calc R . . H11B H -0.3024 0.3715 0.1020 0.049 Uiso 1 1 calc R . . C12 C -0.1743(4) 0.4458(3) 0.03807(11) 0.0421(7) Uani 1 1 d . . . H12A H -0.2820 0.4518 0.0156 0.051 Uiso 1 1 calc R . . C13 C -0.0651(4) 0.5880(3) 0.04114(10) 0.0380(7) Uani 1 1 d . . . C14 C 0.0525(4) 0.5963(3) 0.08751(11) 0.0372(7) Uani 1 1 d . . . H14A H -0.0186 0.6283 0.1171 0.045 Uiso 1 1 calc R . . H14B H 0.1526 0.6683 0.0825 0.045 Uiso 1 1 calc R . . C15 C 0.1617(4) 0.3879(3) 0.03967(10) 0.0414(7) Uani 1 1 d . . . H15A H 0.2772 0.4298 0.0275 0.050 Uiso 1 1 calc R . . H15B H 0.1644 0.2770 0.0362 0.050 Uiso 1 1 calc R . . C16 C 0.0047(5) 0.4544(4) 0.01125(10) 0.0431(7) Uani 1 1 d . . . H16A H 0.0083 0.4594 -0.0263 0.052 Uiso 1 1 calc R . . C17 C 0.3753(4) 0.1109(4) 0.24824(11) 0.0455(8) Uani 1 1 d . . . H17A H 0.3945 0.0271 0.2716 0.068 Uiso 1 1 calc R . . H17B H 0.3360 0.1999 0.2670 0.068 Uiso 1 1 calc R . . H17C H 0.4880 0.1334 0.2306 0.068 Uiso 1 1 calc R . . C18 C 0.3003(4) -0.0729(3) 0.18327(10) 0.0355(6) Uani 1 1 d . . . C19 C 0.0592(4) 0.0627(3) 0.09887(10) 0.0386(7) Uani 1 1 d . . . H19A H 0.0533 -0.0378 0.1140 0.058 Uiso 1 1 calc R . . H19B H 0.1794 0.0790 0.0847 0.058 Uiso 1 1 calc R . . H19C H -0.0310 0.0707 0.0721 0.058 Uiso 1 1 calc R . . C20 C -0.1316(5) 0.7303(4) 0.01708(12) 0.0455(8) Uani 1 1 d . . . H20A H -0.1916 0.7061 -0.0147 0.068 Uiso 1 1 calc R . . H20B H -0.0296 0.7975 0.0106 0.068 Uiso 1 1 calc R . . H20C H -0.2171 0.7802 0.0396 0.068 Uiso 1 1 calc R . . C21 C 0.5234(4) -0.1683(3) 0.12822(11) 0.0445(7) Uani 1 1 d . . . H21A H 0.6306 -0.1349 0.1099 0.067 Uiso 1 1 calc R . . H21B H 0.4370 -0.2122 0.1046 0.067 Uiso 1 1 calc R . . H21C H 0.5579 -0.2440 0.1532 0.067 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 0.0331(15) 0.0389(16) 0.0430(14) 0.0070(12) 0.0021(13) -0.0036(13) O1 0.0560(14) 0.0327(12) 0.0710(14) 0.0042(10) 0.0079(12) -0.0033(11) O2 0.0384(11) 0.0360(10) 0.0490(11) -0.0031(9) 0.0053(10) 0.0006(9) C2 0.0348(16) 0.0470(18) 0.0540(17) 0.0159(15) 0.0094(14) -0.0019(14) C3 0.0422(16) 0.0468(17) 0.0388(14) 0.0120(13) 0.0058(13) 0.0049(15) C4 0.0341(15) 0.0349(14) 0.0349(13) 0.0017(11) -0.0029(12) 0.0005(13) C5 0.0278(13) 0.0288(13) 0.0348(12) -0.0011(11) -0.0015(11) 0.0023(11) C6 0.0289(14) 0.0357(14) 0.0472(15) 0.0036(12) -0.0020(13) 0.0012(13) C7 0.0318(14) 0.0340(14) 0.0492(15) 0.0041(12) -0.0026(13) -0.0045(13) C8 0.0282(13) 0.0302(14) 0.0386(13) 0.0019(11) 0.0015(12) -0.0012(12) C9 0.0295(13) 0.0313(13) 0.0340(12) -0.0003(10) -0.0019(12) -0.0017(12) C10 0.0299(14) 0.0310(13) 0.0342(13) 0.0013(11) 0.0010(11) -0.0028(12) C11 0.0324(15) 0.0421(16) 0.0473(16) 0.0052(13) -0.0079(13) -0.0034(14) C12 0.0435(17) 0.0455(16) 0.0373(13) 0.0006(13) -0.0071(14) -0.0018(14) C13 0.0410(15) 0.0380(15) 0.0349(13) 0.0029(11) 0.0008(13) 0.0026(14) C14 0.0355(15) 0.0329(14) 0.0432(15) 0.0021(11) 0.0000(13) -0.0008(14) C15 0.0500(18) 0.0334(14) 0.0407(14) 0.0016(12) 0.0097(14) 0.0035(14) C16 0.0562(19) 0.0442(16) 0.0289(13) 0.0005(12) 0.0050(13) 0.0037(15) C17 0.0474(17) 0.0463(17) 0.0429(15) -0.0005(13) -0.0093(15) 0.0060(15) C18 0.0327(14) 0.0345(15) 0.0392(14) 0.0025(12) -0.0004(12) -0.0001(13) C19 0.0425(16) 0.0322(14) 0.0410(14) -0.0042(11) -0.0033(14) -0.0019(14) C20 0.0412(16) 0.0436(17) 0.0517(17) 0.0091(14) -0.0008(15) 0.0035(15) C21 0.0456(17) 0.0427(16) 0.0451(15) -0.0083(13) -0.0002(14) 0.0068(15) _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 1.522(4) . ? C1 C10 1.546(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? O1 C18 1.202(3) . ? O2 C18 1.353(3) . ? O2 C21 1.437(3) . ? C2 C3 1.524(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.533(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C18 1.521(4) . ? C4 C17 1.548(4) . ? C4 C5 1.562(4) . ? C5 C6 1.537(4) . ? C5 C10 1.554(3) . ? C5 H5A 1.0000 . ? C6 C7 1.529(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.528(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C14 1.543(4) . ? C8 C9 1.545(4) . ? C8 C15 1.548(4) . ? C9 C11 1.557(4) . ? C9 C10 1.561(4) . ? C9 H9A 1.0000 . ? C10 C19 1.545(4) . ? C11 C12 1.513(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.503(4) . ? C12 C16 1.511(4) . ? C12 H12A 1.0000 . ? C13 C20 1.501(4) . ? C13 C14 1.513(4) . ? C13 C16 1.520(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.510(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? 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 C10 114.2(2) . . ? C2 C1 H1A 108.7 . . ? C10 C1 H1A 108.7 . . ? C2 C1 H1B 108.7 . . ? C10 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C18 O2 C21 116.1(2) . . ? C1 C2 C3 110.7(3) . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 113.6(2) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C18 C4 C3 108.9(2) . . ? C18 C4 C17 105.5(2) . . ? C3 C4 C17 108.0(2) . . ? C18 C4 C5 116.2(2) . . ? C3 C4 C5 108.1(2) . . ? C17 C4 C5 109.9(2) . . ? C6 C5 C10 110.86(19) . . ? C6 C5 C4 117.0(2) . . ? C10 C5 C4 114.9(2) . . ? C6 C5 H5A 104.1 . . ? C10 C5 H5A 104.1 . . ? C4 C5 H5A 104.1 . . ? C7 C6 C5 109.4(2) . . ? C7 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? C7 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? C8 C7 C6 113.6(2) . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C14 111.2(2) . . ? C7 C8 C9 110.5(2) . . ? C14 C8 C9 107.1(2) . . ? C7 C8 C15 114.9(2) . . ? C14 C8 C15 101.2(2) . . ? C9 C8 C15 111.4(2) . . ? C8 C9 C11 109.9(2) . . ? C8 C9 C10 117.3(2) . . ? C11 C9 C10 114.3(2) . . ? C8 C9 H9A 104.7 . . ? C11 C9 H9A 104.7 . . ? C10 C9 H9A 104.7 . . ? C19 C10 C1 108.5(2) . . ? C19 C10 C5 111.6(2) . . ? C1 C10 C5 108.85(19) . . ? C19 C10 C9 114.2(2) . . ? C1 C10 C9 106.3(2) . . ? C5 C10 C9 107.1(2) . . ? C12 C11 C9 113.4(2) . . ? C12 C11 H11A 108.9 . . ? C9 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C9 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C16 60.5(2) . . ? C13 C12 C11 121.9(2) . . ? C16 C12 C11 119.3(3) . . ? C13 C12 H12A 114.8 . . ? C16 C12 H12A 114.8 . . ? C11 C12 H12A 114.8 . . ? C20 C13 C12 120.4(3) . . ? C20 C13 C14 119.8(3) . . ? C12 C13 C14 113.4(2) . . ? C20 C13 C16 123.2(2) . . ? C12 C13 C16 60.0(2) . . ? C14 C13 C16 105.5(2) . . ? C13 C14 C8 105.0(2) . . ? C13 C14 H14A 110.8 . . ? C8 C14 H14A 110.8 . . ? C13 C14 H14B 110.8 . . ? C8 C14 H14B 110.8 . . ? H14A C14 H14B 108.8 . . ? C16 C15 C8 103.5(2) . . ? C16 C15 H15A 111.1 . . ? C8 C15 H15A 111.1 . . ? C16 C15 H15B 111.1 . . ? C8 C15 H15B 111.1 . . ? H15A C15 H15B 109.0 . . ? C15 C16 C12 115.0(2) . . ? C15 C16 C13 107.9(2) . . ? C12 C16 C13 59.5(2) . . ? C15 C16 H16A 119.8 . . ? C12 C16 H16A 119.8 . . ? C13 C16 H16A 119.8 . . ? C4 C17 H17A 109.5 . . ? C4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O1 C18 O2 121.7(3) . . ? O1 C18 C4 126.1(3) . . ? O2 C18 C4 112.1(2) . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C13 C20 H20A 109.5 . . ? C13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 C10 C1 C2 C3 54.4(3) . . . . ? C1 C2 C3 C4 -56.4(4) . . . . ? C2 C3 C4 C18 -72.0(3) . . . . ? C2 C3 C4 C17 173.9(2) . . . . ? C2 C3 C4 C5 55.1(3) . . . . ? C18 C4 C5 C6 -63.8(3) . . . . ? C3 C4 C5 C6 173.5(2) . . . . ? C17 C4 C5 C6 55.8(3) . . . . ? C18 C4 C5 C10 68.9(3) . . . . ? C3 C4 C5 C10 -53.9(3) . . . . ? C17 C4 C5 C10 -171.5(2) . . . . ? C10 C5 C6 C7 63.3(3) . . . . ? C4 C5 C6 C7 -162.3(2) . . . . ? C5 C6 C7 C8 -58.3(3) . . . . ? C6 C7 C8 C14 167.5(2) . . . . ? C6 C7 C8 C9 48.7(3) . . . . ? C6 C7 C8 C15 -78.4(3) . . . . ? C7 C8 C9 C11 -179.1(2) . . . . ? C14 C8 C9 C11 59.6(3) . . . . ? C15 C8 C9 C11 -50.2(3) . . . . ? C7 C8 C9 C10 -46.4(3) . . . . ? C14 C8 C9 C10 -167.7(2) . . . . ? C15 C8 C9 C10 82.5(3) . . . . ? C2 C1 C10 C19 70.0(3) . . . . ? C2 C1 C10 C5 -51.7(3) . . . . ? C2 C1 C10 C9 -166.8(2) . . . . ? C6 C5 C10 C19 67.9(3) . . . . ? C4 C5 C10 C19 -67.6(3) . . . . ? C6 C5 C10 C1 -172.4(2) . . . . ? C4 C5 C10 C1 52.1(3) . . . . ? C6 C5 C10 C9 -57.8(3) . . . . ? C4 C5 C10 C9 166.7(2) . . . . ? C8 C9 C10 C19 -73.4(3) . . . . ? C11 C9 C10 C19 57.4(3) . . . . ? C8 C9 C10 C1 167.0(2) . . . . ? C11 C9 C10 C1 -62.2(3) . . . . ? C8 C9 C10 C5 50.8(3) . . . . ? C11 C9 C10 C5 -178.5(2) . . . . ? C8 C9 C11 C12 -6.9(3) . . . . ? C10 C9 C11 C12 -141.1(2) . . . . ? C9 C11 C12 C13 -30.8(4) . . . . ? C9 C11 C12 C16 40.8(4) . . . . ? C16 C12 C13 C20 113.1(3) . . . . ? C11 C12 C13 C20 -138.8(3) . . . . ? C16 C12 C13 C14 -95.0(3) . . . . ? C11 C12 C13 C14 13.1(4) . . . . ? C11 C12 C13 C16 108.1(3) . . . . ? C20 C13 C14 C8 -168.7(3) . . . . ? C12 C13 C14 C8 39.2(3) . . . . ? C16 C13 C14 C8 -24.3(3) . . . . ? C7 C8 C14 C13 161.7(2) . . . . ? C9 C8 C14 C13 -77.5(3) . . . . ? C15 C8 C14 C13 39.3(3) . . . . ? C7 C8 C15 C16 -158.9(2) . . . . ? C14 C8 C15 C16 -39.0(3) . . . . ? C9 C8 C15 C16 74.5(3) . . . . ? C8 C15 C16 C12 -38.8(3) . . . . ? C8 C15 C16 C13 25.2(3) . . . . ? C13 C12 C16 C15 96.8(3) . . . . ? C11 C12 C16 C15 -15.4(4) . . . . ? C11 C12 C16 C13 -112.2(3) . . . . ? C20 C13 C16 C15 142.2(3) . . . . ? C12 C13 C16 C15 -109.0(3) . . . . ? C14 C13 C16 C15 -0.7(3) . . . . ? C20 C13 C16 C12 -108.8(3) . . . . ? C14 C13 C16 C12 108.4(3) . . . . ? C21 O2 C18 O1 1.6(4) . . . . ? C21 O2 C18 C4 177.7(2) . . . . ? C3 C4 C18 O1 -9.8(4) . . . . ? C17 C4 C18 O1 105.9(3) . . . . ? C5 C4 C18 O1 -132.2(3) . . . . ? C3 C4 C18 O2 174.3(2) . . . . ? C17 C4 C18 O2 -70.0(3) . . . . ? C5 C4 C18 O2 51.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.299 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.048 _publ_requested_category FO _publ_section_references ; Bruker (2001). SAINT, SHELXTL, SMART, XCIF. Bruker AXS, Inc., Madison, Wisconsin, USA. Flack, H. D. (1983), Acta Cryst. A39, 876-881 ; _publ_section_figure_captions ; Figure 1. SHELXTL (Bruker, 2001) plot showing 35% probability ellipsoids for non-H atoms and circles of arbitrary size for H atoms. ; _publ_section_exptl_prep ; Crystals were grown by slow evaporation of solvent from a diethylether / hexane solution. ; _publ_section_exptl_refinement ; Methyl H atom positions, R-CH~3~, were optimized by rotation about R-C bonds with idealized C-H, R--H and H--H distances. Remaining H atoms were included as riding idealized contributors. Methyl H atom U's were assigned as 1.5 times U~eq~ of the carrier atom; remaining H atom U's were assigned as 1.2 times carrier U~eq~. On the basis of 1325 unmerged Friedel opposites, the fractional contribution of the racemic twin was not reliably determined (Flack, 1983). Friedels were merged for final calculations. ; _publ_contact_author ; Scott R. Wilson University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; _publ_contact_author_phone '1 217 244 1708' _publ_contact_author_fax '1 217 244 8068' _publ_contact_author_email srwilson@uiuc.edu _publ_contact_letter ; Please consider this CIF submission for publication as a structural paper in Acta Crystallographica E. ; _publ_requested_journal 'Acta Crystallographica E' _publ_requested_coeditor_name ? _publ_section_title ; ? ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_acknowledgements ; The Materials Chemistry Laboratory at the University of Illinois was supported in part by grants NSF CHE 95-03145 and NSF CHE 03-43032 from the National Science Foundation. ; loop_ _publ_author_name _publ_author_address 'Wilson, Scott R.' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Prussak-Wieckowska, Teresa' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Gao, Yi-Gui' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Ramesh, Maya' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 -1.00 0.1200 0.00 -1.00 2.00 0.1900 0.00 -1.00 -1.00 0.2500 -1.00 1.00 -1.00 0.2200 -1.00 0.00 2.00 0.1600 0.00 1.00 5.00 0.1600 1.00 0.00 -4.00 0.1600 0.00 1.00 -3.00 0.1400