# 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_email qians@mail.sioc.ac.cn loop_ _publ_author_name 'Gang Zhao' 'Shan Qian' data_cd211194 _database_code_depnum_ccdc_archive 'CCDC 839420' #TrackingRef 'cd211194.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 O2' _chemical_formula_weight 246.34 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 P2(1)2(1)2(1) 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 7.0704(14) _cell_length_b 9.5189(19) _cell_length_c 20.411(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1373.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2947 _cell_measurement_theta_min 4.722 _cell_measurement_theta_max 47.840 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.369 _exptl_crystal_size_mid 0.311 _exptl_crystal_size_min 0.269 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.81112 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 7496 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2691 _reflns_number_gt 2428 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0688P)^2^+0.0256P] 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 1.8(13) _chemical_absolute_configuration ad _refine_ls_number_reflns 2691 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.016 _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 O1 O 1.15636(16) 0.43721(12) 0.90479(6) 0.0525(3) Uani 1 1 d . . . O2 O 1.00990(17) 0.64383(11) 0.90074(6) 0.0550(3) Uani 1 1 d . . . C1 C 0.6244(2) 0.04071(16) 0.86831(7) 0.0396(3) Uani 1 1 d . . . C2 C 0.5498(2) -0.05734(18) 0.81436(7) 0.0493(4) Uani 1 1 d . . . H2 H 0.4178 -0.0472 0.8005 0.059 Uiso 1 1 calc R . . C3 C 0.6462(3) -0.19404(18) 0.80229(9) 0.0551(4) Uani 1 1 d . . . H3A H 0.5740 -0.2677 0.7810 0.066 Uiso 1 1 calc R . . H3B H 0.7357 -0.2267 0.8349 0.066 Uiso 1 1 calc R . . C4 C 0.7005(2) -0.06854(18) 0.76204(7) 0.0510(4) Uani 1 1 d . . . H4 H 0.6623 -0.0651 0.7159 0.061 Uiso 1 1 calc R . . C5 C 0.8625(2) 0.02169(16) 0.78430(6) 0.0415(4) Uani 1 1 d . . . C6 C 0.7767(2) 0.12509(15) 0.83124(7) 0.0380(3) Uani 1 1 d . . . H6 H 0.7061 0.1912 0.8037 0.046 Uiso 1 1 calc R . . C7 C 0.8975(2) 0.21603(16) 0.87509(7) 0.0399(3) Uani 1 1 d . . . H7A H 0.9884 0.2677 0.8489 0.048 Uiso 1 1 calc R . . H7B H 0.9667 0.1576 0.9058 0.048 Uiso 1 1 calc R . . C8 C 0.7717(2) 0.31807(15) 0.91232(7) 0.0388(3) Uani 1 1 d . . . C9 C 0.5803(2) 0.26213(17) 0.93512(9) 0.0506(4) Uani 1 1 d . . . H9A H 0.4945 0.3413 0.9386 0.061 Uiso 1 1 calc R . . H9B H 0.5965 0.2242 0.9789 0.061 Uiso 1 1 calc R . . C10 C 0.4834(2) 0.14944(17) 0.89325(8) 0.0489(4) Uani 1 1 d . . . H10A H 0.3870 0.1028 0.9192 0.059 Uiso 1 1 calc R . . H10B H 0.4216 0.1939 0.8562 0.059 Uiso 1 1 calc R . . C11 C 0.7055(3) -0.04209(17) 0.92607(7) 0.0493(4) Uani 1 1 d . . . H11A H 0.8157 -0.0928 0.9120 0.074 Uiso 1 1 calc R . . H11B H 0.6123 -0.1071 0.9419 0.074 Uiso 1 1 calc R . . H11C H 0.7396 0.0217 0.9606 0.074 Uiso 1 1 calc R . . C12 C 1.0393(2) 0.0162(2) 0.76458(8) 0.0548(5) Uani 1 1 d . . . H12A H 1.1265 0.0814 0.7800 0.066 Uiso 1 1 calc R . . H12B H 1.0772 -0.0529 0.7352 0.066 Uiso 1 1 calc R . . C13 C 0.8221(2) 0.44949(16) 0.92683(7) 0.0407(3) Uani 1 1 d . . . C14 C 0.6940(3) 0.55140(18) 0.96217(9) 0.0567(4) Uani 1 1 d . . . H14A H 0.6008 0.5868 0.9322 0.085 Uiso 1 1 calc R . . H14B H 0.7677 0.6281 0.9790 0.085 Uiso 1 1 calc R . . H14C H 0.6322 0.5041 0.9978 0.085 Uiso 1 1 calc R . . C15 C 1.0130(2) 0.50414(15) 0.90962(7) 0.0401(3) Uani 1 1 d . . . C16 C 1.1861(3) 0.7073(2) 0.88243(11) 0.0674(5) Uani 1 1 d . . . H16A H 1.2774 0.6923 0.9165 0.101 Uiso 1 1 calc R . . H16B H 1.1680 0.8063 0.8761 0.101 Uiso 1 1 calc R . . H16C H 1.2307 0.6657 0.8425 0.101 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 O1 0.0426(6) 0.0505(6) 0.0645(7) -0.0030(5) -0.0026(5) 0.0068(6) O2 0.0507(7) 0.0390(6) 0.0752(7) 0.0033(5) 0.0036(6) 0.0005(6) C1 0.0342(7) 0.0397(8) 0.0447(7) 0.0040(6) 0.0016(6) 0.0022(6) C2 0.0362(8) 0.0559(9) 0.0557(9) -0.0005(8) -0.0048(7) -0.0037(8) C3 0.0549(10) 0.0512(9) 0.0592(9) -0.0075(8) -0.0020(8) -0.0071(8) C4 0.0498(10) 0.0609(10) 0.0422(8) -0.0033(7) -0.0052(7) -0.0059(9) C5 0.0433(8) 0.0468(8) 0.0345(7) 0.0017(6) -0.0025(6) 0.0006(7) C6 0.0342(8) 0.0413(8) 0.0385(7) 0.0062(6) -0.0002(6) 0.0036(6) C7 0.0357(8) 0.0393(7) 0.0447(7) -0.0010(6) 0.0037(6) 0.0037(6) C8 0.0393(8) 0.0386(8) 0.0385(7) 0.0071(6) 0.0040(6) 0.0080(6) C9 0.0455(9) 0.0444(9) 0.0621(9) 0.0004(7) 0.0156(8) 0.0070(7) C10 0.0357(8) 0.0488(9) 0.0622(9) 0.0067(7) 0.0084(7) 0.0042(7) C11 0.0583(10) 0.0456(8) 0.0440(8) 0.0058(6) 0.0037(7) 0.0060(8) C12 0.0483(10) 0.0624(11) 0.0538(9) -0.0149(8) 0.0058(7) 0.0008(8) C13 0.0448(9) 0.0399(8) 0.0373(7) 0.0035(6) 0.0035(6) 0.0091(7) C14 0.0596(11) 0.0439(9) 0.0667(10) -0.0029(8) 0.0140(9) 0.0091(8) C15 0.0457(9) 0.0397(8) 0.0349(7) -0.0025(6) -0.0033(6) 0.0054(7) C16 0.0580(12) 0.0510(10) 0.0932(14) -0.0066(10) 0.0067(11) -0.0125(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 O1 C15 1.2011(18) . ? O2 C15 1.3421(19) . ? O2 C16 1.434(2) . ? C1 C10 1.524(2) . ? C1 C11 1.530(2) . ? C1 C2 1.537(2) . ? C1 C6 1.542(2) . ? C2 C3 1.489(2) . ? C2 C4 1.512(2) . ? C2 H2 0.9800 . ? C3 C4 1.500(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.502(2) . ? C4 H4 0.9800 . ? C5 C12 1.315(2) . ? C5 C6 1.502(2) . ? C6 C7 1.510(2) . ? C6 H6 0.9800 . ? C7 C8 1.521(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C13 1.334(2) . ? C8 C9 1.527(2) . ? C9 C10 1.533(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9300 . ? C12 H12B 0.9300 . ? C13 C15 1.489(2) . ? C13 C14 1.510(2) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 C15 O2 C16 115.99(14) . . ? C10 C1 C11 109.74(12) . . ? C10 C1 C2 115.30(13) . . ? C11 C1 C2 111.59(13) . . ? C10 C1 C6 105.48(12) . . ? C11 C1 C6 112.61(13) . . ? C2 C1 C6 101.79(12) . . ? C3 C2 C4 59.95(11) . . ? C3 C2 C1 119.49(14) . . ? C4 C2 C1 107.90(13) . . ? C3 C2 H2 118.3 . . ? C4 C2 H2 118.3 . . ? C1 C2 H2 118.3 . . ? C2 C3 C4 60.78(11) . . ? C2 C3 H3A 117.7 . . ? C4 C3 H3A 117.7 . . ? C2 C3 H3B 117.7 . . ? C4 C3 H3B 117.7 . . ? H3A C3 H3B 114.8 . . ? C3 C4 C5 119.01(14) . . ? C3 C4 C2 59.27(11) . . ? C5 C4 C2 106.46(13) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C2 C4 H4 118.8 . . ? C12 C5 C6 127.29(15) . . ? C12 C5 C4 127.58(15) . . ? C6 C5 C4 105.05(13) . . ? C5 C6 C7 121.69(12) . . ? C5 C6 C1 104.70(12) . . ? C7 C6 C1 113.77(12) . . ? C5 C6 H6 105.1 . . ? C7 C6 H6 105.1 . . ? C1 C6 H6 105.1 . . ? C6 C7 C8 109.35(12) . . ? C6 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? C6 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? C13 C8 C7 123.62(14) . . ? C13 C8 C9 119.74(13) . . ? C7 C8 C9 116.62(13) . . ? C8 C9 C10 118.05(13) . . ? C8 C9 H9A 107.8 . . ? C10 C9 H9A 107.8 . . ? C8 C9 H9B 107.8 . . ? C10 C9 H9B 107.8 . . ? H9A C9 H9B 107.1 . . ? C1 C10 C9 111.65(13) . . ? C1 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C1 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C5 C12 H12A 120.0 . . ? C5 C12 H12B 120.0 . . ? H12A C12 H12B 120.0 . . ? C8 C13 C15 121.16(13) . . ? C8 C13 C14 123.24(15) . . ? C15 C13 C14 115.59(14) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 C15 O2 121.89(16) . . ? O1 C15 C13 126.80(14) . . ? O2 C15 C13 111.29(14) . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 -159.52(14) . . . . ? C11 C1 C2 C3 -33.4(2) . . . . ? C6 C1 C2 C3 86.89(16) . . . . ? C10 C1 C2 C4 135.44(14) . . . . ? C11 C1 C2 C4 -98.49(15) . . . . ? C6 C1 C2 C4 21.84(15) . . . . ? C1 C2 C3 C4 -94.63(16) . . . . ? C2 C3 C4 C5 92.71(16) . . . . ? C1 C2 C4 C3 114.26(15) . . . . ? C3 C2 C4 C5 -114.37(15) . . . . ? C1 C2 C4 C5 -0.12(17) . . . . ? C3 C4 C5 C12 96.9(2) . . . . ? C2 C4 C5 C12 160.47(17) . . . . ? C3 C4 C5 C6 -86.14(17) . . . . ? C2 C4 C5 C6 -22.60(16) . . . . ? C12 C5 C6 C7 -15.6(2) . . . . ? C4 C5 C6 C7 167.46(13) . . . . ? C12 C5 C6 C1 -146.27(17) . . . . ? C4 C5 C6 C1 36.79(14) . . . . ? C10 C1 C6 C5 -156.44(12) . . . . ? C11 C1 C6 C5 83.89(14) . . . . ? C2 C1 C6 C5 -35.72(14) . . . . ? C10 C1 C6 C7 68.40(14) . . . . ? C11 C1 C6 C7 -51.27(16) . . . . ? C2 C1 C6 C7 -170.88(12) . . . . ? C5 C6 C7 C8 175.06(12) . . . . ? C1 C6 C7 C8 -58.23(15) . . . . ? C6 C7 C8 C13 -144.15(14) . . . . ? C6 C7 C8 C9 37.48(17) . . . . ? C13 C8 C9 C10 150.35(14) . . . . ? C7 C8 C9 C10 -31.21(19) . . . . ? C11 C1 C10 C9 65.60(16) . . . . ? C2 C1 C10 C9 -167.38(13) . . . . ? C6 C1 C10 C9 -55.95(15) . . . . ? C8 C9 C10 C1 41.11(19) . . . . ? C7 C8 C13 C15 -2.8(2) . . . . ? C9 C8 C13 C15 175.54(13) . . . . ? C7 C8 C13 C14 178.21(14) . . . . ? C9 C8 C13 C14 -3.5(2) . . . . ? C16 O2 C15 O1 2.6(2) . . . . ? C16 O2 C15 C13 -178.62(14) . . . . ? C8 C13 C15 O1 -28.8(2) . . . . ? C14 C13 C15 O1 150.25(15) . . . . ? C8 C13 C15 O2 152.43(14) . . . . ? C14 C13 C15 O2 -28.50(18) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.157 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.033 # Attachment 'cd211334.cif' data_cd211334 _database_code_depnum_ccdc_archive 'CCDC 839421' #TrackingRef 'cd211334.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H32 O4' _chemical_formula_weight 456.56 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 P2(1)2(1)2(1) 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 11.7192(9) _cell_length_b 12.3720(9) _cell_length_c 16.8928(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2449.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4700 _cell_measurement_theta_min 4.788 _cell_measurement_theta_max 55.136 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.316 _exptl_crystal_size_mid 0.198 _exptl_crystal_size_min 0.157 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.49276 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 13321 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4813 _reflns_number_gt 4216 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0612P)^2^+0.0936P] 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(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 4813 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.011 _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 0.90541(14) 0.75346(13) -0.02017(9) 0.0705(4) Uani 1 1 d . . . O2 O 0.86141(9) 0.63019(9) 0.07108(7) 0.0387(3) Uani 1 1 d . . . O3 O 0.89699(14) 0.23184(12) -0.03449(9) 0.0719(4) Uani 1 1 d . . . O4 O 0.91247(10) 0.34763(9) 0.06695(7) 0.0446(3) Uani 1 1 d . . . C1 C 0.93424(15) 0.67722(14) 0.01790(10) 0.0455(4) Uani 1 1 d . . . C2 C 1.04461(15) 0.62197(14) 0.02151(10) 0.0432(4) Uani 1 1 d . . . C3 C 1.03779(14) 0.54427(13) 0.07567(10) 0.0383(4) Uani 1 1 d . . . C4 C 0.91819(13) 0.54083(12) 0.10822(9) 0.0348(3) Uani 1 1 d . . . C5 C 0.90528(13) 0.53320(13) 0.20014(9) 0.0359(3) Uani 1 1 d . . . H5 H 0.8637 0.5951 0.2221 0.043 Uiso 1 1 calc R . . C6 C 1.02163(14) 0.51673(13) 0.24051(10) 0.0397(4) Uani 1 1 d . . . C7 C 1.09286(14) 0.43546(14) 0.19125(10) 0.0416(4) Uani 1 1 d . . . H7 H 1.0402 0.3764 0.1785 0.050 Uiso 1 1 calc R . . C8 C 1.13194(14) 0.47927(15) 0.11182(11) 0.0445(4) Uani 1 1 d . . . H8A H 1.1989 0.5243 0.1190 0.053 Uiso 1 1 calc R . . H8B H 1.1521 0.4199 0.0770 0.053 Uiso 1 1 calc R . . C9 C 1.01515(16) 0.45966(16) 0.32092(11) 0.0497(4) Uani 1 1 d . . . H9 H 0.9403 0.4367 0.3406 0.060 Uiso 1 1 calc R . . C10 C 1.10921(19) 0.47710(19) 0.37943(12) 0.0647(6) Uani 1 1 d . . . H10A H 1.0923 0.4646 0.4349 0.078 Uiso 1 1 calc R . . H10B H 1.1623 0.5356 0.3693 0.078 Uiso 1 1 calc R . . C11 C 1.11383(17) 0.38068(16) 0.32581(11) 0.0548(5) Uani 1 1 d . . . H11 H 1.0998 0.3091 0.3486 0.066 Uiso 1 1 calc R . . C12 C 1.17683(16) 0.38772(14) 0.24936(11) 0.0486(4) Uani 1 1 d . . . C13 C 1.28109(17) 0.35480(18) 0.23479(13) 0.0622(5) Uani 1 1 d . . . H13A H 1.3241 0.3229 0.2748 0.075 Uiso 1 1 calc R . . H13B H 1.3121 0.3633 0.1845 0.075 Uiso 1 1 calc R . . C14 C 1.07948(16) 0.62795(15) 0.24609(11) 0.0486(4) Uani 1 1 d . . . H14A H 1.0431 0.6700 0.2866 0.073 Uiso 1 1 calc R . . H14B H 1.0728 0.6646 0.1962 0.073 Uiso 1 1 calc R . . H14C H 1.1587 0.6187 0.2589 0.073 Uiso 1 1 calc R . . C15 C 1.14315(18) 0.6590(2) -0.02608(14) 0.0694(6) Uani 1 1 d . . . H15A H 1.2027 0.6833 0.0086 0.104 Uiso 1 1 calc R . . H15B H 1.1198 0.7173 -0.0598 0.104 Uiso 1 1 calc R . . H15C H 1.1708 0.6002 -0.0579 0.104 Uiso 1 1 calc R . . C16 C 0.85654(15) 0.30476(15) 0.00271(11) 0.0477(4) Uani 1 1 d . . . C17 C 0.74705(14) 0.36108(14) -0.00653(10) 0.0425(4) Uani 1 1 d . . . C18 C 0.73902(13) 0.43536(13) 0.04954(9) 0.0374(4) Uani 1 1 d . . . C19 C 0.84596(13) 0.43430(12) 0.09953(10) 0.0362(4) Uani 1 1 d . . . C20 C 0.82814(14) 0.43241(13) 0.19101(10) 0.0377(4) Uani 1 1 d . . . H20 H 0.8620 0.3681 0.2155 0.045 Uiso 1 1 calc R . . C21 C 0.70172(14) 0.44559(14) 0.21283(10) 0.0424(4) Uani 1 1 d . . . C22 C 0.64767(14) 0.53377(13) 0.15912(10) 0.0390(4) Uani 1 1 d . . . H22 H 0.7011 0.5947 0.1594 0.047 Uiso 1 1 calc R . . C23 C 0.63586(14) 0.49974(14) 0.07347(11) 0.0413(4) Uani 1 1 d . . . H23A H 0.5676 0.4563 0.0669 0.050 Uiso 1 1 calc R . . H23B H 0.6290 0.5632 0.0400 0.050 Uiso 1 1 calc R . . C24 C 0.68153(17) 0.49341(17) 0.29539(11) 0.0544(5) Uani 1 1 d . . . H24 H 0.7480 0.5138 0.3273 0.065 Uiso 1 1 calc R . . C25 C 0.5712(2) 0.4711(2) 0.33699(13) 0.0723(6) Uani 1 1 d . . . H25A H 0.5229 0.4143 0.3158 0.087 Uiso 1 1 calc R . . H25B H 0.5700 0.4777 0.3942 0.087 Uiso 1 1 calc R . . C26 C 0.58288(17) 0.57197(18) 0.28989(12) 0.0588(5) Uani 1 1 d . . . H26 H 0.5881 0.6414 0.3176 0.071 Uiso 1 1 calc R . . C27 C 0.54513(15) 0.57039(14) 0.20544(11) 0.0472(4) Uani 1 1 d . . . C28 C 0.44304(17) 0.59348(16) 0.17729(14) 0.0589(5) Uani 1 1 d . . . H28A H 0.3847 0.6135 0.2116 0.071 Uiso 1 1 calc R . . H28B H 0.4294 0.5897 0.1231 0.071 Uiso 1 1 calc R . . C29 C 0.64386(16) 0.33538(15) 0.20186(13) 0.0571(5) Uani 1 1 d . . . H29A H 0.6705 0.3026 0.1538 0.086 Uiso 1 1 calc R . . H29B H 0.5627 0.3450 0.1991 0.086 Uiso 1 1 calc R . . H29C H 0.6621 0.2895 0.2459 0.086 Uiso 1 1 calc R . . C30 C 0.65980(17) 0.32574(18) -0.06523(12) 0.0570(5) Uani 1 1 d . . . H30A H 0.6152 0.2681 -0.0431 0.085 Uiso 1 1 calc R . . H30B H 0.6972 0.3009 -0.1124 0.085 Uiso 1 1 calc R . . H30C H 0.6109 0.3855 -0.0780 0.085 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 O1 0.0735(10) 0.0660(9) 0.0719(10) 0.0333(8) 0.0216(8) 0.0166(8) O2 0.0372(6) 0.0367(6) 0.0422(6) 0.0063(5) 0.0048(5) 0.0027(5) O3 0.0690(10) 0.0683(9) 0.0784(10) -0.0323(8) -0.0104(8) 0.0190(8) O4 0.0374(6) 0.0404(6) 0.0560(7) -0.0090(5) -0.0055(5) 0.0058(5) C1 0.0493(10) 0.0430(9) 0.0441(9) 0.0043(8) 0.0080(8) -0.0009(8) C2 0.0397(9) 0.0468(9) 0.0430(9) -0.0015(8) 0.0059(7) -0.0054(8) C3 0.0335(8) 0.0416(9) 0.0399(8) -0.0064(7) 0.0005(7) -0.0030(7) C4 0.0323(8) 0.0341(8) 0.0378(8) 0.0013(6) -0.0006(7) 0.0013(6) C5 0.0328(8) 0.0354(8) 0.0393(8) 0.0019(7) -0.0001(7) -0.0007(7) C6 0.0361(9) 0.0408(8) 0.0424(9) -0.0028(7) -0.0034(7) 0.0004(7) C7 0.0340(8) 0.0410(9) 0.0498(10) -0.0030(8) -0.0067(7) -0.0004(7) C8 0.0334(9) 0.0502(10) 0.0500(10) -0.0031(8) -0.0001(8) 0.0029(8) C9 0.0461(10) 0.0579(11) 0.0452(10) 0.0032(8) -0.0047(8) 0.0040(8) C10 0.0656(14) 0.0790(14) 0.0494(11) 0.0004(10) -0.0183(10) 0.0094(12) C11 0.0555(11) 0.0553(11) 0.0534(11) 0.0076(9) -0.0123(9) 0.0073(9) C12 0.0446(10) 0.0448(9) 0.0563(11) -0.0036(9) -0.0145(8) 0.0036(8) C13 0.0505(11) 0.0694(13) 0.0667(13) -0.0071(11) -0.0166(10) 0.0141(10) C14 0.0422(9) 0.0478(9) 0.0559(11) -0.0079(9) -0.0054(8) -0.0034(8) C15 0.0501(12) 0.0877(16) 0.0704(13) 0.0136(12) 0.0170(10) -0.0069(11) C16 0.0459(10) 0.0404(9) 0.0570(11) -0.0087(8) -0.0028(8) 0.0019(8) C17 0.0381(9) 0.0414(9) 0.0480(9) -0.0006(8) -0.0024(7) -0.0058(7) C18 0.0335(8) 0.0367(8) 0.0420(9) 0.0047(7) 0.0008(7) -0.0041(7) C19 0.0309(8) 0.0332(8) 0.0445(9) -0.0012(7) 0.0017(7) 0.0012(6) C20 0.0363(8) 0.0338(8) 0.0429(9) 0.0076(7) -0.0036(7) -0.0006(7) C21 0.0364(9) 0.0435(10) 0.0473(9) 0.0092(8) 0.0021(7) -0.0054(7) C22 0.0325(8) 0.0384(9) 0.0462(9) 0.0031(7) 0.0028(7) -0.0006(7) C23 0.0317(8) 0.0450(9) 0.0473(9) 0.0027(7) -0.0038(7) 0.0015(7) C24 0.0485(11) 0.0702(13) 0.0446(10) 0.0069(9) 0.0038(8) -0.0069(9) C25 0.0644(14) 0.0975(17) 0.0549(12) 0.0123(12) 0.0145(11) -0.0110(13) C26 0.0529(11) 0.0710(13) 0.0525(11) -0.0043(10) 0.0135(9) -0.0011(10) C27 0.0406(9) 0.0453(9) 0.0557(11) 0.0026(8) 0.0105(8) -0.0003(8) C28 0.0458(11) 0.0599(12) 0.0711(13) 0.0017(10) 0.0120(9) 0.0116(9) C29 0.0489(11) 0.0501(11) 0.0724(13) 0.0158(10) 0.0003(10) -0.0110(9) C30 0.0520(11) 0.0625(12) 0.0563(11) -0.0129(10) -0.0094(9) -0.0036(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 O1 C1 1.191(2) . ? O2 C1 1.369(2) . ? O2 C4 1.4348(19) . ? O3 C16 1.197(2) . ? O4 C16 1.374(2) . ? O4 C19 1.4353(19) . ? C1 C2 1.464(3) . ? C2 C3 1.329(2) . ? C2 C15 1.480(3) . ? C3 C8 1.496(2) . ? C3 C4 1.506(2) . ? C4 C5 1.563(2) . ? C4 C19 1.573(2) . ? C5 C6 1.538(2) . ? C5 C20 1.548(2) . ? C5 H5 0.9800 . ? C6 C9 1.533(3) . ? C6 C14 1.537(2) . ? C6 C7 1.549(2) . ? C7 C12 1.510(2) . ? C7 C8 1.518(2) . ? C7 H7 0.9800 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.496(3) . ? C9 C11 1.516(3) . ? C9 H9 0.9800 . ? C10 C11 1.499(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.490(3) . ? C11 H11 0.9800 . ? C12 C13 1.311(3) . ? C13 H13A 0.9300 . ? C13 H13B 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.468(2) . ? C17 C18 1.323(2) . ? C17 C30 1.490(2) . ? C18 C23 1.503(2) . ? C18 C19 1.511(2) . ? C19 C20 1.560(2) . ? C20 C21 1.535(2) . ? C20 H20 0.9800 . ? C21 C24 1.533(3) . ? C21 C29 1.534(3) . ? C21 C22 1.554(2) . ? C22 C27 1.504(2) . ? C22 C23 1.513(3) . ? C22 H22 0.9800 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.498(3) . ? C24 C26 1.513(3) . ? C24 H24 0.9800 . ? C25 C26 1.487(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.494(3) . ? C26 H26 0.9800 . ? C27 C28 1.319(3) . ? C28 H28A 0.9300 . ? C28 H28B 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? 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 C1 O2 C4 108.99(12) . . ? C16 O4 C19 109.40(13) . . ? O1 C1 O2 120.95(17) . . ? O1 C1 C2 130.02(17) . . ? O2 C1 C2 108.96(14) . . ? C3 C2 C1 108.25(15) . . ? C3 C2 C15 130.13(18) . . ? C1 C2 C15 121.49(16) . . ? C2 C3 C8 128.71(15) . . ? C2 C3 C4 109.13(14) . . ? C8 C3 C4 121.48(14) . . ? O2 C4 C3 104.48(12) . . ? O2 C4 C5 115.86(13) . . ? C3 C4 C5 117.03(13) . . ? O2 C4 C19 110.80(12) . . ? C3 C4 C19 119.36(13) . . ? C5 C4 C19 89.43(12) . . ? C6 C5 C20 117.08(13) . . ? C6 C5 C4 111.26(13) . . ? C20 C5 C4 90.35(12) . . ? C6 C5 H5 112.1 . . ? C20 C5 H5 112.1 . . ? C4 C5 H5 112.1 . . ? C9 C6 C14 112.33(14) . . ? C9 C6 C5 114.21(14) . . ? C14 C6 C5 107.44(13) . . ? C9 C6 C7 101.76(13) . . ? C14 C6 C7 112.10(14) . . ? C5 C6 C7 109.00(13) . . ? C12 C7 C8 121.18(15) . . ? C12 C7 C6 104.82(14) . . ? C8 C7 C6 113.93(14) . . ? C12 C7 H7 105.2 . . ? C8 C7 H7 105.2 . . ? C6 C7 H7 105.2 . . ? C3 C8 C7 109.29(14) . . ? C3 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? C3 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? C10 C9 C11 59.67(13) . . ? C10 C9 C6 118.85(17) . . ? C11 C9 C6 107.90(15) . . ? C10 C9 H9 118.5 . . ? C11 C9 H9 118.5 . . ? C6 C9 H9 118.5 . . ? C9 C10 C11 60.83(13) . . ? C9 C10 H10A 117.7 . . ? C11 C10 H10A 117.7 . . ? C9 C10 H10B 117.7 . . ? C11 C10 H10B 117.7 . . ? H10A C10 H10B 114.8 . . ? C12 C11 C10 119.68(18) . . ? C12 C11 C9 107.04(15) . . ? C10 C11 C9 59.50(12) . . ? C12 C11 H11 118.4 . . ? C10 C11 H11 118.4 . . ? C9 C11 H11 118.4 . . ? C13 C12 C11 127.31(18) . . ? C13 C12 C7 127.35(19) . . ? C11 C12 C7 105.27(15) . . ? C12 C13 H13A 120.0 . . ? C12 C13 H13B 120.0 . . ? H13A C13 H13B 120.0 . . ? C6 C14 H14A 109.5 . . ? C6 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C6 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C2 C15 H15A 109.5 . . ? C2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 O4 121.09(17) . . ? O3 C16 C17 130.37(18) . . ? O4 C16 C17 108.51(14) . . ? C18 C17 C16 108.40(15) . . ? C18 C17 C30 129.16(17) . . ? C16 C17 C30 122.07(16) . . ? C17 C18 C23 128.15(15) . . ? C17 C18 C19 109.57(14) . . ? C23 C18 C19 121.42(14) . . ? O4 C19 C18 104.04(13) . . ? O4 C19 C20 116.20(13) . . ? C18 C19 C20 116.28(13) . . ? O4 C19 C4 111.68(12) . . ? C18 C19 C4 119.41(13) . . ? C20 C19 C4 89.54(12) . . ? C21 C20 C5 117.00(14) . . ? C21 C20 C19 111.44(13) . . ? C5 C20 C19 90.49(12) . . ? C21 C20 H20 112.1 . . ? C5 C20 H20 112.1 . . ? C19 C20 H20 112.1 . . ? C24 C21 C29 112.62(15) . . ? C24 C21 C20 114.10(15) . . ? C29 C21 C20 107.65(15) . . ? C24 C21 C22 101.37(14) . . ? C29 C21 C22 111.92(14) . . ? C20 C21 C22 109.13(13) . . ? C27 C22 C23 120.55(14) . . ? C27 C22 C21 103.50(14) . . ? C23 C22 C21 113.59(14) . . ? C27 C22 H22 106.1 . . ? C23 C22 H22 106.1 . . ? C21 C22 H22 106.1 . . ? C18 C23 C22 109.33(13) . . ? C18 C23 H23A 109.8 . . ? C22 C23 H23A 109.8 . . ? C18 C23 H23B 109.8 . . ? C22 C23 H23B 109.8 . . ? H23A C23 H23B 108.3 . . ? C25 C24 C26 59.16(14) . . ? C25 C24 C21 119.27(18) . . ? C26 C24 C21 108.05(15) . . ? C25 C24 H24 118.4 . . ? C26 C24 H24 118.4 . . ? C21 C24 H24 118.4 . . ? C26 C25 C24 60.93(14) . . ? C26 C25 H25A 117.7 . . ? C24 C25 H25A 117.7 . . ? C26 C25 H25B 117.7 . . ? C24 C25 H25B 117.7 . . ? H25A C25 H25B 114.8 . . ? C25 C26 C27 118.22(19) . . ? C25 C26 C24 59.90(14) . . ? C27 C26 C24 106.05(16) . . ? C25 C26 H26 119.1 . . ? C27 C26 H26 119.1 . . ? C24 C26 H26 119.1 . . ? C28 C27 C26 127.60(18) . . ? C28 C27 C22 127.06(18) . . ? C26 C27 C22 105.32(15) . . ? C27 C28 H28A 120.0 . . ? C27 C28 H28B 120.0 . . ? H28A C28 H28B 120.0 . . ? C21 C29 H29A 109.5 . . ? C21 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C21 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C17 C30 H30A 109.5 . . ? C17 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C17 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 C4 O2 C1 O1 -179.97(18) . . . . ? C4 O2 C1 C2 -2.65(18) . . . . ? O1 C1 C2 C3 176.8(2) . . . . ? O2 C1 C2 C3 -0.2(2) . . . . ? O1 C1 C2 C15 0.6(3) . . . . ? O2 C1 C2 C15 -176.41(17) . . . . ? C1 C2 C3 C8 -167.62(17) . . . . ? C15 C2 C3 C8 8.1(3) . . . . ? C1 C2 C3 C4 2.86(19) . . . . ? C15 C2 C3 C4 178.6(2) . . . . ? C1 O2 C4 C3 4.17(16) . . . . ? C1 O2 C4 C5 134.47(14) . . . . ? C1 O2 C4 C19 -125.61(14) . . . . ? C2 C3 C4 O2 -4.37(17) . . . . ? C8 C3 C4 O2 166.94(14) . . . . ? C2 C3 C4 C5 -133.97(15) . . . . ? C8 C3 C4 C5 37.3(2) . . . . ? C2 C3 C4 C19 120.11(16) . . . . ? C8 C3 C4 C19 -68.6(2) . . . . ? O2 C4 C5 C6 -130.89(14) . . . . ? C3 C4 C5 C6 -6.88(19) . . . . ? C19 C4 C5 C6 116.17(13) . . . . ? O2 C4 C5 C20 109.72(14) . . . . ? C3 C4 C5 C20 -126.28(14) . . . . ? C19 C4 C5 C20 -3.23(12) . . . . ? C20 C5 C6 C9 -52.15(19) . . . . ? C4 C5 C6 C9 -154.06(14) . . . . ? C20 C5 C6 C14 -177.45(14) . . . . ? C4 C5 C6 C14 80.64(16) . . . . ? C20 C5 C6 C7 60.87(18) . . . . ? C4 C5 C6 C7 -41.04(17) . . . . ? C9 C6 C7 C12 -34.93(17) . . . . ? C14 C6 C7 C12 85.30(17) . . . . ? C5 C6 C7 C12 -155.90(14) . . . . ? C9 C6 C7 C8 -169.61(14) . . . . ? C14 C6 C7 C8 -49.39(19) . . . . ? C5 C6 C7 C8 69.42(17) . . . . ? C2 C3 C8 C7 157.03(17) . . . . ? C4 C3 C8 C7 -12.4(2) . . . . ? C12 C7 C8 C3 -166.52(15) . . . . ? C6 C7 C8 C3 -39.97(19) . . . . ? C14 C6 C9 C10 -33.2(2) . . . . ? C5 C6 C9 C10 -155.87(17) . . . . ? C7 C6 C9 C10 86.87(18) . . . . ? C14 C6 C9 C11 -97.85(17) . . . . ? C5 C6 C9 C11 139.47(15) . . . . ? C7 C6 C9 C11 22.21(17) . . . . ? C6 C9 C10 C11 -94.83(18) . . . . ? C9 C10 C11 C12 93.19(18) . . . . ? C10 C9 C11 C12 -114.87(19) . . . . ? C6 C9 C11 C12 -1.4(2) . . . . ? C6 C9 C11 C10 113.48(18) . . . . ? C10 C11 C12 C13 97.8(2) . . . . ? C9 C11 C12 C13 162.0(2) . . . . ? C10 C11 C12 C7 -85.05(19) . . . . ? C9 C11 C12 C7 -20.91(19) . . . . ? C8 C7 C12 C13 -17.1(3) . . . . ? C6 C7 C12 C13 -147.67(19) . . . . ? C8 C7 C12 C11 165.79(16) . . . . ? C6 C7 C12 C11 35.22(18) . . . . ? C19 O4 C16 O3 179.21(18) . . . . ? C19 O4 C16 C17 -2.28(18) . . . . ? O3 C16 C17 C18 179.0(2) . . . . ? O4 C16 C17 C18 0.7(2) . . . . ? O3 C16 C17 C30 5.3(3) . . . . ? O4 C16 C17 C30 -173.01(16) . . . . ? C16 C17 C18 C23 -168.30(16) . . . . ? C30 C17 C18 C23 4.8(3) . . . . ? C16 C17 C18 C19 1.10(19) . . . . ? C30 C17 C18 C19 174.22(18) . . . . ? C16 O4 C19 C18 2.81(16) . . . . ? C16 O4 C19 C20 131.99(15) . . . . ? C16 O4 C19 C4 -127.29(14) . . . . ? C17 C18 C19 O4 -2.40(17) . . . . ? C23 C18 C19 O4 167.84(14) . . . . ? C17 C18 C19 C20 -131.53(15) . . . . ? C23 C18 C19 C20 38.7(2) . . . . ? C17 C18 C19 C4 122.91(16) . . . . ? C23 C18 C19 C4 -66.8(2) . . . . ? O2 C4 C19 O4 127.48(14) . . . . ? C3 C4 C19 O4 6.10(19) . . . . ? C5 C4 C19 O4 -114.96(13) . . . . ? O2 C4 C19 C18 5.89(19) . . . . ? C3 C4 C19 C18 -115.49(16) . . . . ? C5 C4 C19 C18 123.46(14) . . . . ? O2 C4 C19 C20 -114.36(13) . . . . ? C3 C4 C19 C20 124.26(14) . . . . ? C5 C4 C19 C20 3.20(12) . . . . ? C6 C5 C20 C21 134.53(15) . . . . ? C4 C5 C20 C21 -111.24(15) . . . . ? C6 C5 C20 C19 -110.98(14) . . . . ? C4 C5 C20 C19 3.25(12) . . . . ? O4 C19 C20 C21 -129.75(14) . . . . ? C18 C19 C20 C21 -6.8(2) . . . . ? C4 C19 C20 C21 116.19(14) . . . . ? O4 C19 C20 C5 110.83(14) . . . . ? C18 C19 C20 C5 -126.17(14) . . . . ? C4 C19 C20 C5 -3.23(12) . . . . ? C5 C20 C21 C24 -52.4(2) . . . . ? C19 C20 C21 C24 -154.50(14) . . . . ? C5 C20 C21 C29 -178.12(14) . . . . ? C19 C20 C21 C29 79.74(17) . . . . ? C5 C20 C21 C22 60.22(19) . . . . ? C19 C20 C21 C22 -41.93(18) . . . . ? C24 C21 C22 C27 -37.25(16) . . . . ? C29 C21 C22 C27 83.01(18) . . . . ? C20 C21 C22 C27 -157.95(14) . . . . ? C24 C21 C22 C23 -169.71(14) . . . . ? C29 C21 C22 C23 -49.46(19) . . . . ? C20 C21 C22 C23 69.58(18) . . . . ? C17 C18 C23 C22 153.97(17) . . . . ? C19 C18 C23 C22 -14.3(2) . . . . ? C27 C22 C23 C18 -162.26(14) . . . . ? C21 C22 C23 C18 -38.65(18) . . . . ? C29 C21 C24 C25 -32.8(2) . . . . ? C20 C21 C24 C25 -155.88(18) . . . . ? C22 C21 C24 C25 87.0(2) . . . . ? C29 C21 C24 C26 -96.97(18) . . . . ? C20 C21 C24 C26 139.92(16) . . . . ? C22 C21 C24 C26 22.79(18) . . . . ? C21 C24 C25 C26 -94.5(2) . . . . ? C24 C25 C26 C27 92.96(19) . . . . ? C21 C24 C26 C25 113.85(19) . . . . ? C25 C24 C26 C27 -113.7(2) . . . . ? C21 C24 C26 C27 0.1(2) . . . . ? C25 C26 C27 C28 90.2(3) . . . . ? C24 C26 C27 C28 154.2(2) . . . . ? C25 C26 C27 C22 -88.3(2) . . . . ? C24 C26 C27 C22 -24.25(19) . . . . ? C23 C22 C27 C28 -11.4(3) . . . . ? C21 C22 C27 C28 -139.7(2) . . . . ? C23 C22 C27 C26 167.09(16) . . . . ? C21 C22 C27 C26 38.80(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.168 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.031