# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title ;Indium Tribromide-promoted Arene Terminated Epoxy Olefin Cyclization ; _publ_contact_author_name 'Prof. Teck-Peng Loh' _publ_contact_author_email TECKPENG@NTU.EDU.SG loop_ _publ_author_name 'Teck-Peng Loh' 'Jun-Feng Zhao' 'Yu-Jun Zhao' # Attachment 'CIF_of_2h.txt' data_ltp56m _database_code_depnum_ccdc_archive 'CCDC 669258' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H32 O' _chemical_formula_weight 312.48 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 Cc 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' _cell_length_a 46.416(3) _cell_length_b 7.2645(4) _cell_length_c 10.9433(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.816(5) _cell_angle_gamma 90.00 _cell_volume 3598.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6264 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 29.71 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9832 _exptl_absorpt_correction_T_max 0.9865 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 21178 _diffrn_reflns_av_R_equivalents 0.0804 _diffrn_reflns_av_sigmaI/netI 0.0869 _diffrn_reflns_limit_h_min -56 _diffrn_reflns_limit_h_max 56 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 0.90 _diffrn_reflns_theta_max 25.50 _reflns_number_total 6661 _reflns_number_gt 5755 _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, 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^)+(0.1427P)^2^+14.3321P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(3) _refine_ls_number_reflns 6661 _refine_ls_number_parameters 425 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1034 _refine_ls_R_factor_gt 0.0936 _refine_ls_wR_factor_ref 0.2685 _refine_ls_wR_factor_gt 0.2570 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 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 0.59444(10) 0.5518(7) 0.5112(5) 0.0252(11) Uani 1 1 d . . . H1 H 0.5911 0.5043 0.5927 0.030 Uiso 1 1 calc R . . C2 C 0.58172(11) 0.7501(7) 0.4927(5) 0.0247(10) Uani 1 1 d . . . C3 C 0.59618(12) 0.8619(8) 0.6093(6) 0.0323(12) Uani 1 1 d . . . H3A H 0.5902 0.9912 0.5968 0.048 Uiso 1 1 calc R . . H3B H 0.6177 0.8526 0.6229 0.048 Uiso 1 1 calc R . . H3C H 0.5898 0.8131 0.6825 0.048 Uiso 1 1 calc R . . C4 C 0.58958(13) 0.8421(8) 0.3784(6) 0.0380(13) Uani 1 1 d . . . H4A H 0.5798 0.9623 0.3642 0.057 Uiso 1 1 calc R . . H4B H 0.5829 0.7642 0.3044 0.057 Uiso 1 1 calc R . . H4C H 0.6110 0.8587 0.3935 0.057 Uiso 1 1 calc R . . C5 C 0.54791(10) 0.7333(6) 0.4876(4) 0.0201(10) Uani 1 1 d . . . H5 H 0.5468 0.6754 0.5694 0.024 Uiso 1 1 calc R . . C6 C 0.53170(11) 0.9175(6) 0.4868(5) 0.0240(10) Uani 1 1 d . . . H6A H 0.5437 1.0018 0.5489 0.029 Uiso 1 1 calc R . . H6B H 0.5290 0.9750 0.4030 0.029 Uiso 1 1 calc R . . C7 C 0.50149(11) 0.8883(6) 0.5188(5) 0.0222(10) Uani 1 1 d . . . H7A H 0.4916 1.0091 0.5177 0.027 Uiso 1 1 calc R . . H7B H 0.5046 0.8386 0.6050 0.027 Uiso 1 1 calc R . . C8 C 0.46886(13) 0.8538(7) 0.3014(5) 0.0303(12) Uani 1 1 d . . . H8A H 0.4556 0.7706 0.2446 0.045 Uiso 1 1 calc R . . H8B H 0.4854 0.8883 0.2642 0.045 Uiso 1 1 calc R . . H8C H 0.4580 0.9647 0.3153 0.045 Uiso 1 1 calc R . . C9 C 0.48073(10) 0.7557(6) 0.4280(4) 0.0193(9) Uani 1 1 d . . . C10 C 0.45410(10) 0.7051(8) 0.4825(4) 0.0244(11) Uani 1 1 d . . . C11 C 0.43931(11) 0.8408(8) 0.5358(5) 0.0319(12) Uani 1 1 d . . . H11 H 0.4460 0.9644 0.5370 0.038 Uiso 1 1 calc R . . C12 C 0.41529(12) 0.8015(10) 0.5866(6) 0.0407(15) Uani 1 1 d . . . H12 H 0.4059 0.8965 0.6233 0.049 Uiso 1 1 calc R . . C13 C 0.40484(13) 0.6200(11) 0.5834(6) 0.0474(17) Uani 1 1 d . . . H13 H 0.3887 0.5899 0.6198 0.057 Uiso 1 1 calc R . . C14 C 0.41799(11) 0.4898(10) 0.5284(5) 0.0382(14) Uani 1 1 d . . . H14 H 0.4103 0.3682 0.5249 0.046 Uiso 1 1 calc R . . C15 C 0.44243(11) 0.5227(8) 0.4755(4) 0.0252(10) Uani 1 1 d . . . C16 C 0.45594(12) 0.3692(8) 0.4173(5) 0.0310(12) Uani 1 1 d . . . H16A H 0.4400 0.2992 0.3615 0.037 Uiso 1 1 calc R . . H16B H 0.4659 0.2846 0.4844 0.037 Uiso 1 1 calc R . . C17 C 0.47817(12) 0.4301(7) 0.3421(5) 0.0282(11) Uani 1 1 d . . . H17A H 0.4677 0.4833 0.2611 0.034 Uiso 1 1 calc R . . H17B H 0.4898 0.3230 0.3247 0.034 Uiso 1 1 calc R . . C18 C 0.49892(10) 0.5757(6) 0.4187(4) 0.0181(9) Uani 1 1 d . . . H18 H 0.5036 0.5256 0.5061 0.022 Uiso 1 1 calc R . . C19 C 0.52974(11) 0.6003(6) 0.3860(4) 0.0200(10) Uani 1 1 d . . . C20 C 0.52692(12) 0.6611(8) 0.2489(5) 0.0306(12) Uani 1 1 d . . . H20A H 0.5086 0.6119 0.1971 0.046 Uiso 1 1 calc R . . H20B H 0.5438 0.6143 0.2181 0.046 Uiso 1 1 calc R . . H20C H 0.5266 0.7959 0.2443 0.046 Uiso 1 1 calc R . . C21 C 0.54555(11) 0.4109(6) 0.4032(5) 0.0230(10) Uani 1 1 d . . . H21A H 0.5426 0.3543 0.4818 0.028 Uiso 1 1 calc R . . H21B H 0.5362 0.3294 0.3331 0.028 Uiso 1 1 calc R . . C22 C 0.57901(12) 0.4218(7) 0.4080(5) 0.0287(11) Uani 1 1 d . . . H22A H 0.5878 0.2975 0.4232 0.034 Uiso 1 1 calc R . . H22B H 0.5821 0.4657 0.3262 0.034 Uiso 1 1 calc R . . C23 C 0.17847(10) 0.9469(7) 0.3591(4) 0.0215(10) Uani 1 1 d . . . H23 H 0.1797 0.9974 0.4451 0.026 Uiso 1 1 calc R . . C24 C 0.19147(10) 0.7487(7) 0.3727(5) 0.0230(10) Uani 1 1 d . . . C25 C 0.18633(13) 0.6499(8) 0.2462(6) 0.0350(13) Uani 1 1 d . . . H25A H 0.1660 0.6042 0.2238 0.053 Uiso 1 1 calc R . . H25B H 0.2001 0.5462 0.2520 0.053 Uiso 1 1 calc R . . H25C H 0.1896 0.7360 0.1818 0.053 Uiso 1 1 calc R . . C26 C 0.17492(12) 0.6415(7) 0.4573(5) 0.0320(12) Uani 1 1 d . . . H26A H 0.1816 0.6833 0.5442 0.048 Uiso 1 1 calc R . . H26B H 0.1790 0.5097 0.4523 0.048 Uiso 1 1 calc R . . H26C H 0.1536 0.6635 0.4294 0.048 Uiso 1 1 calc R . . C27 C 0.22510(9) 0.7708(6) 0.4408(4) 0.0172(9) Uani 1 1 d . . . H27 H 0.2248 0.8320 0.5223 0.021 Uiso 1 1 calc R . . C28 C 0.24123(11) 0.5878(6) 0.4772(5) 0.0218(10) Uani 1 1 d . . . H28A H 0.2286 0.5053 0.5150 0.026 Uiso 1 1 calc R . . H28B H 0.2450 0.5271 0.4012 0.026 Uiso 1 1 calc R . . C29 C 0.27044(11) 0.6194(6) 0.5702(5) 0.0218(10) Uani 1 1 d . . . H29A H 0.2803 0.4992 0.5922 0.026 Uiso 1 1 calc R . . H29B H 0.2664 0.6733 0.6478 0.026 Uiso 1 1 calc R . . C30 C 0.29178(10) 0.7490(6) 0.5192(4) 0.0185(9) Uani 1 1 d . . . C31 C 0.30512(12) 0.6463(7) 0.4202(5) 0.0300(11) Uani 1 1 d . . . H31A H 0.3179 0.5466 0.4610 0.045 Uiso 1 1 calc R . . H31B H 0.3167 0.7327 0.3817 0.045 Uiso 1 1 calc R . . H31C H 0.2891 0.5948 0.3554 0.045 Uiso 1 1 calc R . . C32 C 0.31821(10) 0.8007(7) 0.6271(4) 0.0206(10) Uani 1 1 d . . . C33 C 0.33176(11) 0.6671(7) 0.7117(5) 0.0264(11) Uani 1 1 d . . . H33 H 0.3241 0.5454 0.7035 0.032 Uiso 1 1 calc R . . C34 C 0.35614(11) 0.7047(8) 0.8078(5) 0.0312(12) Uani 1 1 d . . . H34 H 0.3648 0.6099 0.8638 0.037 Uiso 1 1 calc R . . C35 C 0.36775(12) 0.8825(9) 0.8215(6) 0.0377(13) Uani 1 1 d . . . H35 H 0.3843 0.9109 0.8872 0.045 Uiso 1 1 calc R . . C36 C 0.35455(11) 1.0181(8) 0.7365(5) 0.0295(11) Uani 1 1 d . . . H36 H 0.3624 1.1395 0.7456 0.035 Uiso 1 1 calc R . . C37 C 0.33022(10) 0.9807(7) 0.6386(5) 0.0233(10) Uani 1 1 d . . . C38 C 0.31700(11) 1.1364(7) 0.5530(6) 0.0294(12) Uani 1 1 d . . . H38A H 0.3331 1.2057 0.5281 0.035 Uiso 1 1 calc R . . H38B H 0.3067 1.2216 0.5998 0.035 Uiso 1 1 calc R . . C39 C 0.29512(11) 1.0719(7) 0.4348(5) 0.0248(11) Uani 1 1 d . . . H39A H 0.3060 1.0172 0.3753 0.030 Uiso 1 1 calc R . . H39B H 0.2836 1.1780 0.3933 0.030 Uiso 1 1 calc R . . C40 C 0.27414(10) 0.9270(6) 0.4719(4) 0.0177(9) Uani 1 1 d . . . H40 H 0.2687 0.9794 0.5482 0.021 Uiso 1 1 calc R . . C41 C 0.24396(10) 0.9000(6) 0.3765(4) 0.0197(9) Uani 1 1 d . . . C42 C 0.24851(13) 0.8351(8) 0.2475(5) 0.0294(11) Uani 1 1 d . . . H42A H 0.2671 0.8850 0.2335 0.044 Uiso 1 1 calc R . . H42B H 0.2321 0.8787 0.1814 0.044 Uiso 1 1 calc R . . H42C H 0.2492 0.7003 0.2459 0.044 Uiso 1 1 calc R . . C43 C 0.22782(11) 1.0892(6) 0.3566(5) 0.0233(10) Uani 1 1 d . . . H43A H 0.2293 1.1481 0.4393 0.028 Uiso 1 1 calc R . . H43B H 0.2382 1.1696 0.3071 0.028 Uiso 1 1 calc R . . C44 C 0.19534(11) 1.0768(7) 0.2901(5) 0.0249(11) Uani 1 1 d . . . H44A H 0.1938 1.0318 0.2034 0.030 Uiso 1 1 calc R . . H44B H 0.1864 1.2009 0.2853 0.030 Uiso 1 1 calc R . . O1 O 0.62570(8) 0.5460(6) 0.5162(4) 0.0396(10) Uani 1 1 d . . . H1A H 0.6285 0.5441 0.4431 0.059 Uiso 1 1 calc R . . O2 O 0.14767(8) 0.9468(6) 0.2936(4) 0.0348(9) Uani 1 1 d . . . H2 H 0.1445 1.0364 0.2439 0.052 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 0.023(2) 0.023(3) 0.031(3) 0.000(2) 0.008(2) 0.0006(19) C2 0.027(2) 0.020(2) 0.027(3) -0.002(2) 0.0057(19) 0.0018(18) C3 0.025(2) 0.025(3) 0.044(3) -0.006(2) 0.002(2) -0.003(2) C4 0.036(3) 0.032(3) 0.049(4) 0.002(3) 0.016(3) -0.007(2) C5 0.027(2) 0.017(2) 0.018(2) -0.0005(18) 0.0074(18) 0.0029(18) C6 0.029(2) 0.014(2) 0.028(3) -0.0014(19) 0.004(2) 0.0021(18) C7 0.028(2) 0.016(2) 0.022(2) -0.0075(19) 0.0033(19) 0.0043(18) C8 0.038(3) 0.023(3) 0.028(3) 0.008(2) 0.002(2) 0.012(2) C9 0.025(2) 0.015(2) 0.016(2) 0.0003(18) 0.0014(17) 0.0054(18) C10 0.020(2) 0.041(3) 0.012(2) 0.000(2) 0.0024(17) 0.004(2) C11 0.025(2) 0.041(3) 0.029(3) -0.005(2) 0.004(2) 0.011(2) C12 0.027(3) 0.064(4) 0.033(3) -0.008(3) 0.010(2) 0.010(3) C13 0.022(3) 0.083(5) 0.037(3) -0.014(3) 0.006(2) -0.009(3) C14 0.016(2) 0.058(4) 0.039(3) -0.001(3) 0.002(2) -0.010(2) C15 0.024(2) 0.033(3) 0.016(2) 0.001(2) -0.0001(18) -0.002(2) C16 0.025(2) 0.030(3) 0.035(3) -0.008(2) 0.001(2) -0.002(2) C17 0.032(3) 0.021(3) 0.028(3) -0.008(2) -0.002(2) 0.003(2) C18 0.030(2) 0.015(2) 0.011(2) -0.0036(17) 0.0074(18) 0.0010(18) C19 0.033(3) 0.015(2) 0.013(2) -0.0038(18) 0.0073(18) 0.0032(18) C20 0.035(3) 0.030(3) 0.027(3) -0.003(2) 0.006(2) -0.003(2) C21 0.029(2) 0.018(2) 0.024(2) -0.004(2) 0.010(2) 0.0002(19) C22 0.032(3) 0.021(3) 0.034(3) -0.002(2) 0.009(2) 0.007(2) C23 0.017(2) 0.024(2) 0.023(2) 0.000(2) 0.0021(18) 0.0043(18) C24 0.020(2) 0.025(3) 0.023(2) 0.000(2) 0.0021(18) -0.0007(19) C25 0.033(3) 0.029(3) 0.040(3) -0.005(2) 0.003(2) -0.001(2) C26 0.032(3) 0.025(3) 0.037(3) 0.007(2) 0.003(2) -0.003(2) C27 0.021(2) 0.017(2) 0.015(2) 0.0000(17) 0.0056(17) 0.0014(17) C28 0.025(2) 0.016(2) 0.025(2) 0.0019(19) 0.0087(19) -0.0006(18) C29 0.028(2) 0.014(2) 0.025(3) 0.0090(19) 0.010(2) 0.0049(18) C30 0.022(2) 0.016(2) 0.020(2) 0.0038(18) 0.0086(17) 0.0037(17) C31 0.039(3) 0.025(3) 0.029(3) -0.004(2) 0.014(2) 0.005(2) C32 0.016(2) 0.022(2) 0.028(3) 0.002(2) 0.0133(19) 0.0025(18) C33 0.022(2) 0.030(3) 0.029(3) 0.001(2) 0.010(2) 0.004(2) C34 0.017(2) 0.038(3) 0.038(3) 0.007(2) 0.007(2) 0.005(2) C35 0.025(3) 0.047(3) 0.040(3) 0.001(3) 0.004(2) 0.005(2) C36 0.020(2) 0.034(3) 0.037(3) -0.002(2) 0.012(2) 0.000(2) C37 0.021(2) 0.023(2) 0.028(3) -0.008(2) 0.0094(19) 0.0008(19) C38 0.023(2) 0.022(3) 0.045(3) 0.004(2) 0.011(2) -0.0011(19) C39 0.027(2) 0.017(2) 0.033(3) 0.008(2) 0.012(2) 0.0011(18) C40 0.023(2) 0.018(2) 0.016(2) 0.0043(18) 0.0125(18) 0.0020(17) C41 0.024(2) 0.016(2) 0.021(2) 0.0031(18) 0.0070(18) 0.0027(18) C42 0.040(3) 0.030(3) 0.019(2) 0.007(2) 0.009(2) 0.004(2) C43 0.032(3) 0.016(2) 0.023(2) 0.0044(19) 0.008(2) 0.0013(19) C44 0.023(2) 0.022(2) 0.029(3) 0.006(2) 0.004(2) 0.0085(18) O1 0.0250(18) 0.054(3) 0.041(2) -0.009(2) 0.0103(16) 0.0023(17) O2 0.0197(17) 0.040(2) 0.042(2) 0.0063(18) 0.0006(15) 0.0055(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 O1 1.440(6) . ? C1 C22 1.524(7) . ? C1 C2 1.553(7) . ? C2 C4 1.531(8) . ? C2 C3 1.536(7) . ? C2 C5 1.563(7) . ? C5 C6 1.534(6) . ? C5 C19 1.570(6) . ? C6 C7 1.534(7) . ? C7 C9 1.555(6) . ? C8 C9 1.547(7) . ? C9 C10 1.532(7) . ? C9 C18 1.572(6) . ? C10 C11 1.400(7) . ? C10 C15 1.427(8) . ? C11 C12 1.381(8) . ? C12 C13 1.403(10) . ? C13 C14 1.339(9) . ? C14 C15 1.403(7) . ? C15 C16 1.490(8) . ? C16 C17 1.521(8) . ? C17 C18 1.546(7) . ? C18 C19 1.560(7) . ? C19 C20 1.541(7) . ? C19 C21 1.551(6) . ? C21 C22 1.544(7) . ? C23 O2 1.450(6) . ? C23 C44 1.529(7) . ? C23 C24 1.556(7) . ? C24 C25 1.530(8) . ? C24 C26 1.539(7) . ? C24 C27 1.582(6) . ? C27 C28 1.534(6) . ? C27 C41 1.554(6) . ? C28 C29 1.521(7) . ? C29 C30 1.557(6) . ? C30 C32 1.548(7) . ? C30 C31 1.553(7) . ? C30 C40 1.556(6) . ? C32 C33 1.392(7) . ? C32 C37 1.416(7) . ? C33 C34 1.390(7) . ? C34 C35 1.395(8) . ? C35 C36 1.399(8) . ? C36 C37 1.400(7) . ? C37 C38 1.509(7) . ? C38 C39 1.530(8) . ? C39 C40 1.548(6) . ? C40 C41 1.563(6) . ? C41 C42 1.546(7) . ? C41 C43 1.557(6) . ? C43 C44 1.525(7) . ? 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 C22 108.3(4) . . ? O1 C1 C2 112.5(4) . . ? C22 C1 C2 112.1(4) . . ? C4 C2 C3 108.0(4) . . ? C4 C2 C1 111.0(4) . . ? C3 C2 C1 107.4(4) . . ? C4 C2 C5 115.1(4) . . ? C3 C2 C5 108.7(4) . . ? C1 C2 C5 106.4(4) . . ? C6 C5 C2 114.8(4) . . ? C6 C5 C19 110.3(4) . . ? C2 C5 C19 116.8(4) . . ? C7 C6 C5 110.5(4) . . ? C6 C7 C9 114.1(4) . . ? C10 C9 C8 107.5(4) . . ? C10 C9 C7 109.8(4) . . ? C8 C9 C7 109.5(4) . . ? C10 C9 C18 108.5(4) . . ? C8 C9 C18 114.5(4) . . ? C7 C9 C18 106.9(4) . . ? C11 C10 C15 117.4(5) . . ? C11 C10 C9 120.4(5) . . ? C15 C10 C9 122.1(4) . . ? C12 C11 C10 122.4(6) . . ? C11 C12 C13 119.3(6) . . ? C14 C13 C12 119.0(6) . . ? C13 C14 C15 123.8(6) . . ? C14 C15 C10 117.9(5) . . ? C14 C15 C16 120.3(5) . . ? C10 C15 C16 121.8(5) . . ? C15 C16 C17 114.4(5) . . ? C16 C17 C18 108.7(4) . . ? C17 C18 C19 116.5(4) . . ? C17 C18 C9 109.0(4) . . ? C19 C18 C9 116.9(4) . . ? C20 C19 C21 107.9(4) . . ? C20 C19 C18 111.9(4) . . ? C21 C19 C18 107.7(4) . . ? C20 C19 C5 115.4(4) . . ? C21 C19 C5 107.1(4) . . ? C18 C19 C5 106.5(3) . . ? C22 C21 C19 113.8(4) . . ? C1 C22 C21 111.1(4) . . ? O2 C23 C44 108.2(4) . . ? O2 C23 C24 111.5(4) . . ? C44 C23 C24 112.8(4) . . ? C25 C24 C26 108.0(4) . . ? C25 C24 C23 111.6(4) . . ? C26 C24 C23 106.9(4) . . ? C25 C24 C27 114.4(4) . . ? C26 C24 C27 109.9(4) . . ? C23 C24 C27 105.8(4) . . ? C28 C27 C41 110.5(4) . . ? C28 C27 C24 114.1(4) . . ? C41 C27 C24 116.4(4) . . ? C29 C28 C27 110.8(4) . . ? C28 C29 C30 113.3(4) . . ? C32 C30 C31 106.1(4) . . ? C32 C30 C40 108.8(4) . . ? C31 C30 C40 115.4(4) . . ? C32 C30 C29 109.4(4) . . ? C31 C30 C29 110.1(4) . . ? C40 C30 C29 107.0(3) . . ? C33 C32 C37 118.3(4) . . ? C33 C32 C30 120.2(4) . . ? C37 C32 C30 121.4(4) . . ? C34 C33 C32 122.5(5) . . ? C33 C34 C35 119.6(5) . . ? C34 C35 C36 118.6(5) . . ? C35 C36 C37 122.2(5) . . ? C36 C37 C32 118.8(5) . . ? C36 C37 C38 118.5(5) . . ? C32 C37 C38 122.6(4) . . ? C37 C38 C39 113.4(4) . . ? C38 C39 C40 108.9(4) . . ? C39 C40 C30 109.7(4) . . ? C39 C40 C41 115.7(4) . . ? C30 C40 C41 116.4(4) . . ? C42 C41 C27 115.7(4) . . ? C42 C41 C43 107.5(4) . . ? C27 C41 C43 107.1(4) . . ? C42 C41 C40 111.4(4) . . ? C27 C41 C40 106.6(4) . . ? C43 C41 C40 108.3(4) . . ? C44 C43 C41 114.1(4) . . ? C43 C44 C23 111.2(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.467 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.097 # Attachment 'CIF_of_2i.txt' data_ltp67o _database_code_depnum_ccdc_archive 'CCDC 669259' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_absolute_configuration unk _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H34 O' _chemical_formula_sum 'C23 H34 O' _chemical_formula_weight 326.50 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 Pna2(1) 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' _cell_length_a 10.9577(3) _cell_length_b 7.2339(2) _cell_length_c 46.7378(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3704.76(18) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6255 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 26.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9810 _exptl_absorpt_correction_T_max 0.9932 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 21949 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -58 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 0.87 _diffrn_reflns_theta_max 26.38 _reflns_number_total 6949 _reflns_number_gt 5900 _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, 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^)+(0.0656P)^2^+0.1625P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(14) _refine_ls_number_reflns 6949 _refine_ls_number_parameters 445 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1097 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.105 _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 0.9394(2) 0.1976(3) 0.54202(5) 0.0212(5) Uani 1 1 d . . . H1 H 1.0240 0.2494 0.5428 0.025 Uiso 1 1 calc R . . C2 C 0.8558(2) 0.3257(3) 0.55843(5) 0.0243(6) Uani 1 1 d . . . H2A H 0.7710 0.2790 0.5572 0.029 Uiso 1 1 calc R . . H2B H 0.8580 0.4501 0.5496 0.029 Uiso 1 1 calc R . . C3 C 0.8932(2) 0.3403(3) 0.58984(5) 0.0220(5) Uani 1 1 d . . . H3A H 0.8342 0.4207 0.6000 0.026 Uiso 1 1 calc R . . H3B H 0.9744 0.3999 0.5910 0.026 Uiso 1 1 calc R . . C4 C 0.8990(2) 0.1504(3) 0.60531(5) 0.0168(5) Uani 1 1 d . . . C5 C 0.7676(2) 0.0826(3) 0.61003(5) 0.0237(5) Uani 1 1 d . . . H5A H 0.7163 0.1225 0.5940 0.036 Uiso 1 1 calc R . . H5B H 0.7357 0.1347 0.6279 0.036 Uiso 1 1 calc R . . H5C H 0.7670 -0.0526 0.6112 0.036 Uiso 1 1 calc R . . C6 C 0.9801(2) 0.0208(3) 0.58657(5) 0.0164(5) Uani 1 1 d . . . H6 H 1.0615 0.0832 0.5860 0.020 Uiso 1 1 calc R . . C7 C 0.9426(2) -0.0017(3) 0.55444(5) 0.0193(5) Uani 1 1 d . . . C8 C 0.8211(2) -0.1021(3) 0.54966(6) 0.0274(6) Uani 1 1 d . . . H8A H 0.8141 -0.1379 0.5295 0.041 Uiso 1 1 calc R . . H8B H 0.7535 -0.0198 0.5547 0.041 Uiso 1 1 calc R . . H8C H 0.8181 -0.2130 0.5617 0.041 Uiso 1 1 calc R . . C9 C 1.0423(3) -0.1088(3) 0.53833(5) 0.0286(6) Uani 1 1 d . . . H9A H 1.0380 -0.2399 0.5435 0.043 Uiso 1 1 calc R . . H9B H 1.1226 -0.0596 0.5435 0.043 Uiso 1 1 calc R . . H9C H 1.0298 -0.0952 0.5177 0.043 Uiso 1 1 calc R . . C10 C 1.0036(2) -0.1618(3) 0.60211(5) 0.0204(5) Uani 1 1 d . . . H10A H 0.9248 -0.2245 0.6058 0.025 Uiso 1 1 calc R . . H10B H 1.0533 -0.2436 0.5898 0.025 Uiso 1 1 calc R . . C11 C 1.0699(2) -0.1306(3) 0.63041(5) 0.0190(5) Uani 1 1 d . . . H11A H 1.1513 -0.0772 0.6264 0.023 Uiso 1 1 calc R . . H11B H 1.0825 -0.2515 0.6399 0.023 Uiso 1 1 calc R . . C12 C 1.0007(2) -0.0007(3) 0.65123(5) 0.0168(5) Uani 1 1 d . . . C13 C 0.8908(2) -0.1062(3) 0.66398(5) 0.0231(5) Uani 1 1 d . . . H13A H 0.9203 -0.2030 0.6769 0.035 Uiso 1 1 calc R . . H13B H 0.8433 -0.1625 0.6485 0.035 Uiso 1 1 calc R . . H13C H 0.8390 -0.0199 0.6746 0.035 Uiso 1 1 calc R . . C14 C 0.9678(2) 0.1779(3) 0.63421(5) 0.0157(5) Uani 1 1 d . . . H14 H 1.0485 0.2313 0.6286 0.019 Uiso 1 1 calc R . . C15 C 0.9125(2) 0.3216(3) 0.65468(5) 0.0220(5) Uani 1 1 d . . . H15A H 0.8809 0.4280 0.6436 0.026 Uiso 1 1 calc R . . H15B H 0.8437 0.2659 0.6654 0.026 Uiso 1 1 calc R . . C16 C 1.0100(2) 0.3868(3) 0.67550(5) 0.0235(6) Uani 1 1 d . . . H16A H 1.0653 0.4733 0.6654 0.028 Uiso 1 1 calc R . . H16B H 0.9702 0.4558 0.6912 0.028 Uiso 1 1 calc R . . C17 C 1.0852(2) 0.2319(3) 0.68823(5) 0.0198(5) Uani 1 1 d . . . C18 C 1.0833(2) 0.0522(3) 0.67638(5) 0.0173(5) Uani 1 1 d . . . C19 C 1.1572(2) -0.0806(3) 0.68966(5) 0.0229(5) Uani 1 1 d . . . H19 H 1.1560 -0.2036 0.6825 0.028 Uiso 1 1 calc R . . C20 C 1.2314(2) -0.0402(4) 0.71261(5) 0.0261(6) Uani 1 1 d . . . H20 H 1.2805 -0.1347 0.7208 0.031 Uiso 1 1 calc R . . C21 C 1.2353(2) 0.1386(4) 0.72401(5) 0.0261(6) Uani 1 1 d . . . C22 C 1.3196(3) 0.1867(5) 0.74823(6) 0.0392(7) Uani 1 1 d . . . H22A H 1.4013 0.2121 0.7407 0.059 Uiso 1 1 calc R . . H22B H 1.3236 0.0829 0.7617 0.059 Uiso 1 1 calc R . . H22C H 1.2888 0.2966 0.7582 0.059 Uiso 1 1 calc R . . C23 C 1.1607(2) 0.2699(3) 0.71128(5) 0.0242(6) Uani 1 1 d . . . H23 H 1.1613 0.3920 0.7188 0.029 Uiso 1 1 calc R . . C24 C 0.8276(2) 0.6977(3) 0.96094(5) 0.0236(5) Uani 1 1 d . . . H24 H 0.7426 0.7448 0.9583 0.028 Uiso 1 1 calc R . . C25 C 0.9133(2) 0.8293(3) 0.94581(5) 0.0257(6) Uani 1 1 d . . . H25A H 0.9984 0.7872 0.9486 0.031 Uiso 1 1 calc R . . H25B H 0.9055 0.9538 0.9544 0.031 Uiso 1 1 calc R . . C26 C 0.8869(2) 0.8418(3) 0.91393(5) 0.0220(5) Uani 1 1 d . . . H26A H 0.9486 0.9231 0.9049 0.026 Uiso 1 1 calc R . . H26B H 0.8060 0.9004 0.9112 0.026 Uiso 1 1 calc R . . C27 C 0.8874(2) 0.6535(3) 0.89836(5) 0.0176(5) Uani 1 1 d . . . C28 C 1.0206(2) 0.5896(3) 0.89520(6) 0.0250(5) Uani 1 1 d . . . H28A H 1.0237 0.4542 0.8950 0.037 Uiso 1 1 calc R . . H28B H 1.0688 0.6364 0.9113 0.037 Uiso 1 1 calc R . . H28C H 1.0543 0.6375 0.8772 0.037 Uiso 1 1 calc R . . C29 C 0.8049(2) 0.5190(3) 0.91593(5) 0.0166(5) Uani 1 1 d . . . H29 H 0.7223 0.5775 0.9153 0.020 Uiso 1 1 calc R . . C30 C 0.8331(2) 0.5002(3) 0.94850(5) 0.0199(5) Uani 1 1 d . . . C31 C 0.9552(3) 0.4061(4) 0.95551(6) 0.0326(6) Uani 1 1 d . . . H31A H 0.9588 0.3788 0.9760 0.049 Uiso 1 1 calc R . . H31B H 1.0226 0.4886 0.9503 0.049 Uiso 1 1 calc R . . H31C H 0.9620 0.2907 0.9446 0.049 Uiso 1 1 calc R . . C32 C 0.7307(3) 0.3871(4) 0.96264(5) 0.0297(6) Uani 1 1 d . . . H32A H 0.7383 0.2570 0.9570 0.045 Uiso 1 1 calc R . . H32B H 0.6513 0.4346 0.9564 0.045 Uiso 1 1 calc R . . H32C H 0.7371 0.3976 0.9835 0.045 Uiso 1 1 calc R . . C33 C 0.7883(2) 0.3362(3) 0.90008(5) 0.0204(5) Uani 1 1 d . . . H33A H 0.8690 0.2779 0.8970 0.025 Uiso 1 1 calc R . . H33B H 0.7384 0.2513 0.9119 0.025 Uiso 1 1 calc R . . C34 C 0.7261(2) 0.3663(3) 0.87130(5) 0.0200(5) Uani 1 1 d . . . H34A H 0.6433 0.4164 0.8746 0.024 Uiso 1 1 calc R . . H34B H 0.7171 0.2454 0.8616 0.024 Uiso 1 1 calc R . . C35 C 0.7957(2) 0.4987(3) 0.85140(5) 0.0168(5) Uani 1 1 d . . . C36 C 0.9089(2) 0.3977(3) 0.83911(5) 0.0250(6) Uani 1 1 d . . . H36A H 0.8822 0.2996 0.8261 0.037 Uiso 1 1 calc R . . H36B H 0.9561 0.3436 0.8548 0.037 Uiso 1 1 calc R . . H36C H 0.9599 0.4862 0.8287 0.037 Uiso 1 1 calc R . . C37 C 0.8244(2) 0.6781(3) 0.86870(5) 0.0165(5) Uani 1 1 d . . . H37 H 0.7423 0.7302 0.8734 0.020 Uiso 1 1 calc R . . C38 C 0.8820(2) 0.8232(3) 0.84883(5) 0.0218(5) Uani 1 1 d . . . H38A H 0.9109 0.9301 0.8602 0.026 Uiso 1 1 calc R . . H38B H 0.9530 0.7690 0.8387 0.026 Uiso 1 1 calc R . . C39 C 0.7872(2) 0.8860(3) 0.82730(5) 0.0255(6) Uani 1 1 d . . . H39A H 0.7306 0.9732 0.8368 0.031 Uiso 1 1 calc R . . H39B H 0.8288 0.9539 0.8117 0.031 Uiso 1 1 calc R . . C40 C 0.7136(2) 0.7305(3) 0.81437(5) 0.0215(5) Uani 1 1 d . . . C41 C 0.7152(2) 0.5517(3) 0.82570(5) 0.0188(5) Uani 1 1 d . . . C42 C 0.6420(2) 0.4185(3) 0.81244(5) 0.0231(5) Uani 1 1 d . . . H42 H 0.6429 0.2956 0.8196 0.028 Uiso 1 1 calc R . . C43 C 0.5686(2) 0.4592(4) 0.78937(5) 0.0262(6) Uani 1 1 d . . . H43 H 0.5207 0.3645 0.7809 0.031 Uiso 1 1 calc R . . C44 C 0.5640(2) 0.6384(4) 0.77835(5) 0.0274(6) Uani 1 1 d . . . C45 C 0.4787(3) 0.6863(4) 0.75407(6) 0.0371(7) Uani 1 1 d . . . H45A H 0.3948 0.6932 0.7613 0.056 Uiso 1 1 calc R . . H45B H 0.4838 0.5908 0.7393 0.056 Uiso 1 1 calc R . . H45C H 0.5020 0.8060 0.7459 0.056 Uiso 1 1 calc R . . C46 C 0.6383(2) 0.7701(4) 0.79100(5) 0.0252(6) Uani 1 1 d . . . H46 H 0.6380 0.8921 0.7835 0.030 Uiso 1 1 calc R . . O1 O 0.90069(17) 0.1951(3) 0.51244(4) 0.0309(4) Uani 1 1 d . . . H1A H 0.9598 0.2235 0.5019 0.046 Uiso 1 1 calc R . . O2 O 0.85472(17) 0.7028(3) 0.99090(4) 0.0324(4) Uani 1 1 d . . . H2 H 0.7896 0.6943 1.0003 0.049 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 0.0206(12) 0.0248(12) 0.0184(13) 0.0006(10) -0.0035(10) -0.0006(10) C2 0.0258(12) 0.0215(12) 0.0257(15) 0.0085(10) -0.0023(11) 0.0027(11) C3 0.0239(13) 0.0186(12) 0.0235(14) 0.0011(10) 0.0018(10) 0.0054(10) C4 0.0167(12) 0.0153(10) 0.0186(13) 0.0026(9) 0.0011(10) 0.0021(10) C5 0.0140(12) 0.0320(13) 0.0252(13) 0.0035(10) 0.0014(10) 0.0011(11) C6 0.0126(11) 0.0179(11) 0.0186(12) 0.0002(9) -0.0002(9) 0.0006(9) C7 0.0183(12) 0.0197(11) 0.0199(13) -0.0006(9) -0.0026(9) -0.0002(10) C8 0.0304(14) 0.0274(12) 0.0243(14) 0.0012(10) -0.0091(11) -0.0055(12) C9 0.0328(14) 0.0294(13) 0.0235(14) -0.0050(10) -0.0016(11) 0.0031(12) C10 0.0238(13) 0.0151(10) 0.0225(13) -0.0018(9) -0.0012(10) 0.0022(10) C11 0.0216(12) 0.0139(10) 0.0215(13) 0.0009(9) 0.0011(10) 0.0004(10) C12 0.0143(11) 0.0155(11) 0.0206(13) 0.0010(9) 0.0001(9) 0.0018(9) C13 0.0233(13) 0.0247(12) 0.0213(14) 0.0061(9) 0.0002(10) -0.0022(11) C14 0.0140(11) 0.0144(10) 0.0188(12) -0.0007(8) 0.0023(9) 0.0005(10) C15 0.0217(12) 0.0219(12) 0.0224(13) 0.0001(10) 0.0045(10) 0.0066(10) C16 0.0287(14) 0.0198(11) 0.0220(14) -0.0044(10) 0.0047(11) 0.0012(11) C17 0.0200(12) 0.0216(11) 0.0179(13) -0.0005(9) 0.0074(10) -0.0025(10) C18 0.0145(11) 0.0205(11) 0.0171(12) 0.0031(9) 0.0052(9) -0.0006(10) C19 0.0228(12) 0.0244(12) 0.0216(13) 0.0016(10) -0.0014(10) 0.0010(10) C20 0.0183(13) 0.0366(14) 0.0233(14) 0.0038(11) 0.0000(10) 0.0040(12) C21 0.0213(13) 0.0413(15) 0.0157(13) -0.0019(11) 0.0023(10) -0.0047(12) C22 0.0307(15) 0.0593(19) 0.0276(16) -0.0087(13) -0.0046(12) -0.0018(14) C23 0.0221(13) 0.0296(13) 0.0211(14) -0.0076(11) 0.0035(10) -0.0044(12) C24 0.0220(13) 0.0284(13) 0.0203(14) -0.0057(10) -0.0019(10) -0.0016(11) C25 0.0246(13) 0.0224(13) 0.0302(16) -0.0051(10) -0.0034(11) -0.0030(11) C26 0.0228(12) 0.0150(11) 0.0282(15) -0.0014(9) -0.0029(11) -0.0039(10) C27 0.0125(11) 0.0167(11) 0.0236(13) -0.0025(9) 0.0005(10) 0.0000(10) C28 0.0139(11) 0.0309(13) 0.0301(14) -0.0008(11) 0.0006(10) -0.0017(11) C29 0.0131(10) 0.0140(11) 0.0226(13) -0.0006(9) -0.0006(10) 0.0005(9) C30 0.0197(12) 0.0212(11) 0.0190(13) 0.0004(9) -0.0002(10) -0.0001(10) C31 0.0325(15) 0.0293(14) 0.0360(16) 0.0045(11) -0.0072(12) 0.0028(13) C32 0.0358(15) 0.0316(13) 0.0218(13) 0.0018(10) 0.0019(11) -0.0096(12) C33 0.0249(13) 0.0138(11) 0.0226(13) 0.0009(9) 0.0025(11) -0.0004(10) C34 0.0209(12) 0.0152(10) 0.0238(13) -0.0054(9) 0.0007(10) -0.0030(10) C35 0.0148(11) 0.0168(11) 0.0190(12) -0.0026(9) 0.0032(9) 0.0013(10) C36 0.0237(13) 0.0235(13) 0.0277(15) -0.0071(10) 0.0034(10) 0.0047(11) C37 0.0128(11) 0.0155(11) 0.0212(13) -0.0005(9) 0.0027(10) -0.0012(9) C38 0.0244(13) 0.0179(12) 0.0231(13) -0.0005(10) 0.0034(11) -0.0052(11) C39 0.0315(14) 0.0201(12) 0.0248(14) 0.0036(10) 0.0039(11) -0.0030(11) C40 0.0172(12) 0.0258(12) 0.0214(13) -0.0018(10) 0.0058(10) 0.0036(11) C41 0.0142(11) 0.0245(12) 0.0176(12) -0.0023(10) 0.0044(9) 0.0026(10) C42 0.0229(13) 0.0238(12) 0.0226(13) -0.0028(10) 0.0013(10) -0.0001(11) C43 0.0229(13) 0.0354(13) 0.0204(13) -0.0056(11) -0.0006(10) -0.0026(12) C44 0.0176(12) 0.0441(15) 0.0206(14) 0.0002(11) 0.0035(10) 0.0048(12) C45 0.0296(15) 0.0553(17) 0.0265(15) 0.0052(12) -0.0027(12) 0.0034(14) C46 0.0268(14) 0.0289(13) 0.0200(15) 0.0031(10) 0.0061(10) 0.0048(12) O1 0.0326(10) 0.0420(10) 0.0181(10) 0.0052(8) -0.0020(7) 0.0004(9) O2 0.0341(10) 0.0433(10) 0.0198(10) -0.0059(8) -0.0035(8) -0.0067(9) _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 1.446(3) . ? C1 C2 1.512(3) . ? C1 C7 1.555(3) . ? C2 C3 1.528(4) . ? C3 C4 1.553(3) . ? C4 C5 1.537(3) . ? C4 C14 1.560(3) . ? C4 C6 1.561(3) . ? C6 C10 1.530(3) . ? C6 C7 1.565(3) . ? C7 C8 1.533(3) . ? C7 C9 1.537(3) . ? C10 C11 1.526(3) . ? C11 C12 1.551(3) . ? C12 C18 1.532(3) . ? C12 C13 1.545(3) . ? C12 C14 1.559(3) . ? C14 C15 1.538(3) . ? C15 C16 1.520(4) . ? C16 C17 1.512(3) . ? C17 C23 1.386(3) . ? C17 C18 1.414(3) . ? C18 C19 1.401(3) . ? C19 C20 1.378(4) . ? C20 C21 1.400(4) . ? C21 C23 1.387(4) . ? C21 C22 1.501(4) . ? C24 O2 1.432(3) . ? C24 C25 1.513(4) . ? C24 C30 1.544(3) . ? C25 C26 1.521(4) . ? C26 C27 1.544(3) . ? C27 C28 1.538(3) . ? C27 C37 1.559(3) . ? C27 C29 1.561(3) . ? C29 C33 1.526(3) . ? C29 C30 1.559(3) . ? C30 C31 1.536(3) . ? C30 C32 1.538(3) . ? C33 C34 1.524(3) . ? C34 C35 1.537(3) . ? C35 C41 1.539(3) . ? C35 C36 1.549(3) . ? C35 C37 1.561(3) . ? C37 C38 1.537(3) . ? C38 C39 1.517(4) . ? C39 C40 1.509(3) . ? C40 C41 1.398(3) . ? C40 C46 1.399(4) . ? C41 C42 1.399(3) . ? C42 C43 1.377(4) . ? C43 C44 1.396(4) . ? C44 C46 1.385(4) . ? C44 C45 1.511(4) . ? 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 108.33(19) . . ? O1 C1 C7 110.60(18) . . ? C2 C1 C7 113.1(2) . . ? C1 C2 C3 111.5(2) . . ? C2 C3 C4 113.39(19) . . ? C5 C4 C3 108.14(19) . . ? C5 C4 C14 111.65(19) . . ? C3 C4 C14 108.07(18) . . ? C5 C4 C6 114.98(18) . . ? C3 C4 C6 107.04(19) . . ? C14 C4 C6 106.68(17) . . ? C10 C6 C4 110.39(18) . . ? C10 C6 C7 114.18(18) . . ? C4 C6 C7 116.83(18) . . ? C8 C7 C9 107.9(2) . . ? C8 C7 C1 111.45(19) . . ? C9 C7 C1 107.49(19) . . ? C8 C7 C6 114.67(19) . . ? C9 C7 C6 109.64(18) . . ? C1 C7 C6 105.51(18) . . ? C11 C10 C6 111.32(18) . . ? C10 C11 C12 113.62(19) . . ? C18 C12 C13 106.73(18) . . ? C18 C12 C11 110.10(18) . . ? C13 C12 C11 108.93(17) . . ? C18 C12 C14 108.71(17) . . ? C13 C12 C14 115.20(18) . . ? C11 C12 C14 107.15(18) . . ? C15 C14 C12 109.51(18) . . ? C15 C14 C4 115.75(18) . . ? C12 C14 C4 116.62(17) . . ? C16 C15 C14 109.32(19) . . ? C17 C16 C15 113.90(19) . . ? C23 C17 C18 119.7(2) . . ? C23 C17 C16 119.0(2) . . ? C18 C17 C16 121.3(2) . . ? C19 C18 C17 116.6(2) . . ? C19 C18 C12 120.7(2) . . ? C17 C18 C12 122.6(2) . . ? C20 C19 C18 122.7(2) . . ? C19 C20 C21 120.7(2) . . ? C23 C21 C20 116.8(2) . . ? C23 C21 C22 121.8(2) . . ? C20 C21 C22 121.3(2) . . ? C17 C23 C21 123.3(2) . . ? O2 C24 C25 108.2(2) . . ? O2 C24 C30 112.6(2) . . ? C25 C24 C30 112.5(2) . . ? C24 C25 C26 112.2(2) . . ? C25 C26 C27 114.1(2) . . ? C28 C27 C26 108.29(19) . . ? C28 C27 C37 111.7(2) . . ? C26 C27 C37 108.45(18) . . ? C28 C27 C29 114.37(18) . . ? C26 C27 C29 107.44(19) . . ? C37 C27 C29 106.42(17) . . ? C33 C29 C30 114.94(18) . . ? C33 C29 C27 110.70(18) . . ? C30 C29 C27 116.93(18) . . ? C31 C30 C32 107.9(2) . . ? C31 C30 C24 111.3(2) . . ? C32 C30 C24 107.6(2) . . ? C31 C30 C29 114.8(2) . . ? C32 C30 C29 108.72(19) . . ? C24 C30 C29 106.20(18) . . ? C34 C33 C29 110.98(18) . . ? C33 C34 C35 113.66(19) . . ? C34 C35 C41 110.05(18) . . ? C34 C35 C36 109.12(18) . . ? C41 C35 C36 106.68(18) . . ? C34 C35 C37 107.73(18) . . ? C41 C35 C37 108.21(17) . . ? C36 C35 C37 115.01(19) . . ? C38 C37 C27 115.69(18) . . ? C38 C37 C35 109.73(19) . . ? C27 C37 C35 117.05(17) . . ? C39 C38 C37 108.9(2) . . ? C40 C39 C38 114.1(2) . . ? C41 C40 C46 119.5(2) . . ? C41 C40 C39 122.1(2) . . ? C46 C40 C39 118.4(2) . . ? C40 C41 C42 117.6(2) . . ? C40 C41 C35 122.2(2) . . ? C42 C41 C35 120.2(2) . . ? C43 C42 C41 122.3(2) . . ? C42 C43 C44 120.6(2) . . ? C46 C44 C43 117.4(2) . . ? C46 C44 C45 121.7(2) . . ? C43 C44 C45 120.8(2) . . ? C44 C46 C40 122.6(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.281 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.067