# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'I. Fleming' 'Thomas Butler' 'Sabine Gonsior' 'Bo-Hye Kim' 'D. D. Sung' 'Hee-Gweon Woo' _publ_contact_author_name 'Prof I Fleming' _publ_contact_author_address ; University Chemistry Laboratory University of Cambridge Lensfield Road CAMBRIDGE CB2 1EW ; _publ_contact_author_email IF10000@CAM.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; A synthesis of (+-)-sparteine ; data_if0102 _database_code_depnum_ccdc_archive 'CCDC 263438' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 Br O4' _chemical_formula_weight 357.24 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' Br Br -0.2901 2.4595 '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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.3004(5) _cell_length_b 14.8301(9) _cell_length_c 11.6244(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.528(3) _cell_angle_gamma 90.00 _cell_volume 1520.20(13) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5361 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 2.717 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_process_details ; Sortav Blessing (1995) multi-scan from symmetry-related measurements (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method 'fine slice omega/phi scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8450 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2640 _reflns_number_gt 2121 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution ; TEXSAN: Molecular Structure Corporation (1995). Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA' ; _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0557P)^2^+1.9938P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2640 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.009 _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 0.1280(4) 0.3279(2) 0.4927(3) 0.0228(8) Uani 1 1 d . . . C2 C -0.0064(4) 0.3775(3) 0.5134(4) 0.0318(9) Uani 1 1 d . . . H2A H 0.0290 0.4181 0.5844 0.038 Uiso 1 1 calc R . . H2B H -0.0609 0.4137 0.4412 0.038 Uiso 1 1 calc R . . C3 C -0.1068(4) 0.3061(3) 0.5353(4) 0.0344(9) Uani 1 1 d . . . H3A H -0.1955 0.2968 0.4620 0.041 Uiso 1 1 calc R . . H3B H -0.1437 0.3234 0.6033 0.041 Uiso 1 1 calc R . . C4 C -0.0116(4) 0.2190(3) 0.5668(4) 0.0329(9) Uani 1 1 d . . . H4A H 0.0540 0.2181 0.6526 0.039 Uiso 1 1 calc R . . H4B H -0.0759 0.1643 0.5492 0.039 Uiso 1 1 calc R . . C5 C 0.0809(4) 0.2292(2) 0.4793(3) 0.0242(8) Uani 1 1 d . . . H5 H 0.0098 0.2207 0.3950 0.029 Uiso 1 1 calc R . . C6 C 0.2214(4) 0.1697(2) 0.4926(3) 0.0230(8) Uani 1 1 d . . . H6 H 0.2014 0.1312 0.4185 0.028 Uiso 1 1 calc R . . C7 C 0.3604(4) 0.2310(2) 0.5024(3) 0.0223(8) Uani 1 1 d . . . C8 C 0.3194(4) 0.2946(2) 0.3885(3) 0.0238(8) Uani 1 1 d . . . H8 H 0.2882 0.2570 0.3133 0.029 Uiso 1 1 calc R . . C9 C 0.4472(4) 0.3594(3) 0.3835(4) 0.0314(9) Uani 1 1 d . . . H9A H 0.5196 0.3699 0.4656 0.038 Uiso 1 1 calc R . . H9B H 0.5031 0.3349 0.3307 0.038 Uiso 1 1 calc R . . C10 C 0.3641(5) 0.4461(3) 0.3307(4) 0.0343(9) Uani 1 1 d . . . H10A H 0.3176 0.4416 0.2416 0.041 Uiso 1 1 calc R . . H10B H 0.4334 0.4986 0.3500 0.041 Uiso 1 1 calc R . . C11 C 0.2432(5) 0.4532(3) 0.3935(4) 0.0326(9) Uani 1 1 d . . . H11A H 0.1609 0.4948 0.3492 0.039 Uiso 1 1 calc R . . H11B H 0.2875 0.4746 0.4781 0.039 Uiso 1 1 calc R . . C12 C 0.1847(4) 0.3564(2) 0.3898(3) 0.0245(8) Uani 1 1 d . . . H12 H 0.1007 0.3477 0.3117 0.029 Uiso 1 1 calc R . . O13 O 0.2563(3) 0.33812(17) 0.6076(2) 0.0258(6) Uani 1 1 d . . . C14 C 0.3839(4) 0.2938(2) 0.6092(3) 0.0231(8) Uani 1 1 d . . . O15 O 0.5013(3) 0.30900(18) 0.6885(2) 0.0304(6) Uani 1 1 d . . . C16 C 0.5070(4) 0.1785(3) 0.5197(3) 0.0303(9) Uani 1 1 d . . . H16A H 0.5286 0.1409 0.5937 0.036 Uiso 1 1 calc R . . H16B H 0.5919 0.2215 0.5318 0.036 Uiso 1 1 calc R . . Br17 Br 0.49573(6) 0.10095(3) 0.38122(4) 0.0525(2) Uani 1 1 d . . . C18 C 0.2480(4) 0.1085(2) 0.6027(3) 0.0270(8) Uani 1 1 d . . . O19 O 0.3331(3) 0.1237(2) 0.7022(2) 0.0411(7) Uani 1 1 d . . . O20 O 0.1563(3) 0.03732(17) 0.5745(2) 0.0309(6) Uani 1 1 d . . . C21 C 0.1547(5) -0.0197(3) 0.6755(4) 0.0363(9) Uani 1 1 d . . . H21A H 0.0712 -0.0630 0.6485 0.055 Uiso 1 1 calc R . . H21B H 0.1408 0.0177 0.7407 0.055 Uiso 1 1 calc R . . H21C H 0.2511 -0.0523 0.7057 0.055 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 0.0186(18) 0.0286(19) 0.0191(17) 0.0004(15) 0.0028(14) 0.0004(15) C2 0.031(2) 0.035(2) 0.031(2) 0.0019(17) 0.0122(17) 0.0112(17) C3 0.0152(19) 0.038(2) 0.048(2) -0.012(2) 0.0075(17) 0.0061(16) C4 0.029(2) 0.038(2) 0.038(2) 0.0012(19) 0.0191(17) -0.0027(17) C5 0.0195(18) 0.031(2) 0.0208(18) 0.0009(15) 0.0043(14) -0.0017(15) C6 0.0228(19) 0.0250(18) 0.0194(18) -0.0030(15) 0.0040(14) -0.0055(15) C7 0.0186(18) 0.0255(19) 0.0216(18) 0.0020(15) 0.0048(14) -0.0005(15) C8 0.0216(19) 0.0294(19) 0.0199(17) -0.0023(16) 0.0059(14) 0.0007(15) C9 0.027(2) 0.037(2) 0.034(2) -0.0001(18) 0.0142(17) -0.0011(17) C10 0.035(2) 0.034(2) 0.037(2) 0.0071(18) 0.0165(18) -0.0044(18) C11 0.036(2) 0.028(2) 0.038(2) 0.0059(17) 0.0164(18) 0.0030(17) C12 0.0228(19) 0.031(2) 0.0196(18) 0.0001(15) 0.0058(14) 0.0022(15) O13 0.0232(13) 0.0320(14) 0.0208(13) -0.0046(11) 0.0048(10) -0.0018(11) C14 0.021(2) 0.0271(19) 0.0213(18) 0.0047(16) 0.0069(15) -0.0002(15) O15 0.0230(14) 0.0378(16) 0.0251(13) 0.0019(12) 0.0003(11) -0.0067(11) C16 0.023(2) 0.036(2) 0.031(2) 0.0015(17) 0.0085(16) 0.0049(16) Br17 0.0562(3) 0.0570(4) 0.0486(3) -0.0083(2) 0.0230(2) 0.0218(2) C18 0.0201(19) 0.033(2) 0.026(2) 0.0027(17) 0.0045(16) -0.0015(16) O19 0.0380(17) 0.0505(18) 0.0258(15) 0.0092(13) -0.0025(13) -0.0183(14) O20 0.0317(15) 0.0270(14) 0.0316(14) 0.0051(12) 0.0068(11) -0.0074(12) C21 0.040(2) 0.033(2) 0.038(2) 0.0094(18) 0.0154(18) -0.0039(19) _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 O13 1.489(4) . ? C1 C12 1.513(5) . ? C1 C5 1.521(5) . ? C1 C2 1.533(5) . ? C2 C3 1.487(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.542(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.534(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.544(5) . ? C5 H5 1.0000 . ? C6 C18 1.524(5) . ? C6 C7 1.554(5) . ? C6 H6 1.0000 . ? C7 C14 1.511(5) . ? C7 C16 1.527(5) . ? C7 C8 1.570(5) . ? C8 C9 1.544(5) . ? C8 C12 1.555(5) . ? C8 H8 1.0000 . ? C9 C10 1.525(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.527(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.532(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12 1.0000 . ? O13 C14 1.352(4) . ? C14 O15 1.205(4) . ? C16 Br17 1.954(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C18 O19 1.198(4) . ? C18 O20 1.331(4) . ? O20 C21 1.451(5) . ? 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 O13 C1 C12 107.4(3) . . ? O13 C1 C5 108.2(3) . . ? C12 C1 C5 110.4(3) . . ? O13 C1 C2 105.7(3) . . ? C12 C1 C2 119.7(3) . . ? C5 C1 C2 104.8(3) . . ? C3 C2 C1 105.9(3) . . ? C3 C2 H2A 110.6 . . ? C1 C2 H2A 110.6 . . ? C3 C2 H2B 110.6 . . ? C1 C2 H2B 110.6 . . ? H2A C2 H2B 108.7 . . ? C2 C3 C4 107.0(3) . . ? C2 C3 H3A 110.3 . . ? C4 C3 H3A 110.3 . . ? C2 C3 H3B 110.3 . . ? C4 C3 H3B 110.3 . . ? H3A C3 H3B 108.6 . . ? C5 C4 C3 99.3(3) . . ? C5 C4 H4A 111.9 . . ? C3 C4 H4A 111.9 . . ? C5 C4 H4B 111.9 . . ? C3 C4 H4B 111.9 . . ? H4A C4 H4B 109.6 . . ? C1 C5 C4 103.3(3) . . ? C1 C5 C6 109.4(3) . . ? C4 C5 C6 120.8(3) . . ? C1 C5 H5 107.5 . . ? C4 C5 H5 107.5 . . ? C6 C5 H5 107.5 . . ? C18 C6 C5 109.3(3) . . ? C18 C6 C7 112.2(3) . . ? C5 C6 C7 109.3(3) . . ? C18 C6 H6 108.6 . . ? C5 C6 H6 108.6 . . ? C7 C6 H6 108.6 . . ? C14 C7 C16 108.4(3) . . ? C14 C7 C6 108.7(3) . . ? C16 C7 C6 113.4(3) . . ? C14 C7 C8 104.8(3) . . ? C16 C7 C8 112.7(3) . . ? C6 C7 C8 108.4(3) . . ? C9 C8 C12 105.4(3) . . ? C9 C8 C7 114.9(3) . . ? C12 C8 C7 109.1(3) . . ? C9 C8 H8 109.1 . . ? C12 C8 H8 109.1 . . ? C7 C8 H8 109.1 . . ? C10 C9 C8 104.0(3) . . ? C10 C9 H9A 111.0 . . ? C8 C9 H9A 111.0 . . ? C10 C9 H9B 111.0 . . ? C8 C9 H9B 111.0 . . ? H9A C9 H9B 109.0 . . ? C9 C10 C11 102.8(3) . . ? C9 C10 H10A 111.2 . . ? C11 C10 H10A 111.2 . . ? C9 C10 H10B 111.2 . . ? C11 C10 H10B 111.2 . . ? H10A C10 H10B 109.1 . . ? C10 C11 C12 103.3(3) . . ? C10 C11 H11A 111.1 . . ? C12 C11 H11A 111.1 . . ? C10 C11 H11B 111.1 . . ? C12 C11 H11B 111.1 . . ? H11A C11 H11B 109.1 . . ? C1 C12 C11 116.7(3) . . ? C1 C12 C8 109.1(3) . . ? C11 C12 C8 105.8(3) . . ? C1 C12 H12 108.3 . . ? C11 C12 H12 108.3 . . ? C8 C12 H12 108.3 . . ? C14 O13 C1 114.3(3) . . ? O15 C14 O13 119.8(3) . . ? O15 C14 C7 127.1(3) . . ? O13 C14 C7 113.0(3) . . ? C7 C16 Br17 112.3(2) . . ? C7 C16 H16A 109.1 . . ? Br17 C16 H16A 109.1 . . ? C7 C16 H16B 109.1 . . ? Br17 C16 H16B 109.1 . . ? H16A C16 H16B 107.9 . . ? O19 C18 O20 124.2(3) . . ? O19 C18 C6 125.5(3) . . ? O20 C18 C6 110.2(3) . . ? C18 O20 C21 115.7(3) . . ? O20 C21 H21A 109.5 . . ? O20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O20 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 O13 C1 C2 C3 -103.3(3) . . . . ? C12 C1 C2 C3 135.4(3) . . . . ? C5 C1 C2 C3 11.0(4) . . . . ? C1 C2 C3 C4 17.1(4) . . . . ? C2 C3 C4 C5 -37.8(4) . . . . ? O13 C1 C5 C4 77.6(3) . . . . ? C12 C1 C5 C4 -165.1(3) . . . . ? C2 C1 C5 C4 -34.9(4) . . . . ? O13 C1 C5 C6 -52.3(3) . . . . ? C12 C1 C5 C6 65.0(4) . . . . ? C2 C1 C5 C6 -164.8(3) . . . . ? C3 C4 C5 C1 43.8(3) . . . . ? C3 C4 C5 C6 166.5(3) . . . . ? C1 C5 C6 C18 117.6(3) . . . . ? C4 C5 C6 C18 -2.1(4) . . . . ? C1 C5 C6 C7 -5.6(4) . . . . ? C4 C5 C6 C7 -125.3(3) . . . . ? C18 C6 C7 C14 -63.8(4) . . . . ? C5 C6 C7 C14 57.6(4) . . . . ? C18 C6 C7 C16 56.8(4) . . . . ? C5 C6 C7 C16 178.3(3) . . . . ? C18 C6 C7 C8 -177.2(3) . . . . ? C5 C6 C7 C8 -55.7(3) . . . . ? C14 C7 C8 C9 64.9(4) . . . . ? C16 C7 C8 C9 -52.8(4) . . . . ? C6 C7 C8 C9 -179.2(3) . . . . ? C14 C7 C8 C12 -53.2(3) . . . . ? C16 C7 C8 C12 -170.9(3) . . . . ? C6 C7 C8 C12 62.7(4) . . . . ? C12 C8 C9 C10 -22.6(4) . . . . ? C7 C8 C9 C10 -142.8(3) . . . . ? C8 C9 C10 C11 40.3(4) . . . . ? C9 C10 C11 C12 -42.4(4) . . . . ? O13 C1 C12 C11 -59.6(4) . . . . ? C5 C1 C12 C11 -177.4(3) . . . . ? C2 C1 C12 C11 60.9(4) . . . . ? O13 C1 C12 C8 60.2(4) . . . . ? C5 C1 C12 C8 -57.6(4) . . . . ? C2 C1 C12 C8 -179.3(3) . . . . ? C10 C11 C12 C1 149.6(3) . . . . ? C10 C11 C12 C8 28.1(4) . . . . ? C9 C8 C12 C1 -129.8(3) . . . . ? C7 C8 C12 C1 -5.8(4) . . . . ? C9 C8 C12 C11 -3.4(4) . . . . ? C7 C8 C12 C11 120.5(3) . . . . ? C12 C1 O13 C14 -54.7(4) . . . . ? C5 C1 O13 C14 64.5(3) . . . . ? C2 C1 O13 C14 176.3(3) . . . . ? C1 O13 C14 O15 167.9(3) . . . . ? C1 O13 C14 C7 -9.7(4) . . . . ? C16 C7 C14 O15 7.9(5) . . . . ? C6 C7 C14 O15 131.6(4) . . . . ? C8 C7 C14 O15 -112.7(4) . . . . ? C16 C7 C14 O13 -174.8(3) . . . . ? C6 C7 C14 O13 -51.0(4) . . . . ? C8 C7 C14 O13 64.7(3) . . . . ? C14 C7 C16 Br17 -175.8(2) . . . . ? C6 C7 C16 Br17 63.3(3) . . . . ? C8 C7 C16 Br17 -60.4(4) . . . . ? C5 C6 C18 O19 -95.6(4) . . . . ? C7 C6 C18 O19 25.8(5) . . . . ? C5 C6 C18 O20 80.8(4) . . . . ? C7 C6 C18 O20 -157.8(3) . . . . ? O19 C18 O20 C21 4.9(5) . . . . ? C6 C18 O20 C21 -171.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.901 _refine_diff_density_min -0.970 _refine_diff_density_rms 0.135 data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 263439' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H24 O4' _chemical_formula_sum 'C17 H24 O4' _chemical_formula_weight 292.36 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6393(2) _cell_length_b 9.6637(2) _cell_length_c 17.7208(4) _cell_angle_alpha 78.7280(10) _cell_angle_beta 79.0190(10) _cell_angle_gamma 76.7810(10) _cell_volume 1557.50(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6981 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 20.39 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Although the cell dimensions suggest a C-centred monoclinic cell, R(merge) in this setting clearly indicates that this structure is triclinic (JED)! ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 9537 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 20.39 _reflns_number_total 3046 _reflns_number_gt 2790 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0376P)^2^+0.9436P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3046 _refine_ls_number_parameters 383 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0904 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.019 _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_1 C 0.2203(3) 0.2913(2) 0.62341(12) 0.0342(6) Uani 1 1 d . . . H1A_1 H 0.3177 0.2767 0.6377 0.041 Uiso 1 1 calc R . . H1B_1 H 0.1529 0.2623 0.6704 0.041 Uiso 1 1 calc R . . C2_1 C 0.1692(3) 0.4472(3) 0.58789(13) 0.0463(7) Uani 1 1 d . . . H2A_1 H 0.2010 0.5143 0.6136 0.056 Uiso 1 1 calc R . . H2B_1 H 0.0629 0.4717 0.5917 0.056 Uiso 1 1 calc R . . C3A_1 C 0.2288(2) 0.3089(2) 0.48198(12) 0.0305(6) Uani 1 1 d . . . H3A_1 H 0.1351 0.3233 0.4623 0.037 Uiso 1 1 calc R . . C3_1 C 0.2418(3) 0.4514(3) 0.50333(13) 0.0478(7) Uani 1 1 d . . . H3B_1 H 0.3443 0.4582 0.4981 0.057 Uiso 1 1 calc R . . H3C_1 H 0.1922 0.5346 0.4695 0.057 Uiso 1 1 calc R . . C4_1 C 0.3510(2) 0.2530(2) 0.41985(12) 0.0278(6) Uani 1 1 d . . . H4_1 H 0.4401 0.2145 0.4445 0.033 Uiso 1 1 calc R . . C5_1 C 0.3224(2) 0.1340(2) 0.38302(12) 0.0294(6) Uani 1 1 d . . . H5A_1 H 0.3957 0.1207 0.3362 0.035 Uiso 1 1 calc R . . H5B_1 H 0.2270 0.1669 0.3654 0.035 Uiso 1 1 calc R . . C6A_1 C 0.2053(2) -0.0137(2) 0.50639(12) 0.0276(6) Uani 1 1 d . . . H6A_1 H 0.1110 0.0295 0.4876 0.033 Uiso 1 1 calc R . . C6_1 C 0.3242(2) -0.0126(2) 0.43554(12) 0.0284(6) Uani 1 1 d . . . H6_1 H 0.4190 -0.0425 0.4551 0.034 Uiso 1 1 calc R . . C7_1 C 0.1973(3) -0.1673(2) 0.54999(13) 0.0344(6) Uani 1 1 d . . . H7A_1 H 0.1305 -0.2088 0.5290 0.041 Uiso 1 1 calc R . . H7B_1 H 0.2937 -0.2311 0.5450 0.041 Uiso 1 1 calc R . . C8_1 C 0.1418(3) -0.1496(2) 0.63477(13) 0.0380(6) Uani 1 1 d . . . H8A_1 H 0.0354 -0.1193 0.6437 0.046 Uiso 1 1 calc R . . H8B_1 H 0.1703 -0.2404 0.6702 0.046 Uiso 1 1 calc R . . C9_1 C 0.2138(3) -0.0329(2) 0.64636(13) 0.0357(6) Uani 1 1 d . . . H9A_1 H 0.1572 0.0180 0.6892 0.043 Uiso 1 1 calc R . . H9B_1 H 0.3124 -0.0741 0.6585 0.043 Uiso 1 1 calc R . . C10_1 C 0.2181(2) 0.0682(2) 0.56922(12) 0.0258(5) Uani 1 1 d . . . C11_1 C 0.2228(2) 0.2066(2) 0.55945(12) 0.0261(6) Uani 1 1 d . . . O12_1 O 0.29308(17) 0.44890(17) 0.31581(9) 0.0388(4) Uani 1 1 d . . . C12_1 C 0.3806(3) 0.3739(2) 0.35443(13) 0.0282(6) Uani 1 1 d . . . O13_1 O 0.51909(16) 0.38504(16) 0.34243(8) 0.0346(4) Uani 1 1 d . . . C13_1 C 0.5606(3) 0.4945(2) 0.27916(13) 0.0378(6) Uani 1 1 d . . . H13A_1 H 0.6632 0.4946 0.2759 0.057 Uiso 1 1 calc R . . H13B_1 H 0.5035 0.5891 0.2887 0.057 Uiso 1 1 calc R . . H13C_1 H 0.5431 0.4742 0.2301 0.057 Uiso 1 1 calc R . . O14_1 O 0.19266(18) -0.09371(17) 0.35983(10) 0.0479(5) Uani 1 1 d . . . C14_1 C 0.1755(3) -0.1844(3) 0.30792(16) 0.0559(8) Uani 1 1 d . . . H14A_1 H 0.0811 -0.1499 0.2906 0.084 Uiso 1 1 calc R . . H14B_1 H 0.1822 -0.2836 0.3352 0.084 Uiso 1 1 calc R . . H14C_1 H 0.2517 -0.1812 0.2626 0.084 Uiso 1 1 calc R . . O15_1 O 0.4123(2) -0.2171(2) 0.36977(14) 0.0840(8) Uani 1 1 d . . . C15_1 C 0.3178(3) -0.1195(3) 0.38557(13) 0.0334(6) Uani 1 1 d . . . C1_2 C 0.4625(2) 0.2277(3) 0.16391(12) 0.0357(6) Uani 1 1 d . . . H1A_2 H 0.4193 0.3283 0.1713 0.043 Uiso 1 1 calc R . . H1B_2 H 0.5133 0.1789 0.2084 0.043 Uiso 1 1 calc R . . C2_2 C 0.3475(2) 0.1483(3) 0.15642(13) 0.0382(6) Uani 1 1 d . . . H2A_2 H 0.2561 0.1787 0.1907 0.046 Uiso 1 1 calc R . . H2B_2 H 0.3800 0.0427 0.1692 0.046 Uiso 1 1 calc R . . C3A_2 C 0.4838(2) 0.1985(2) 0.02702(12) 0.0282(6) Uani 1 1 d . . . H3A_2 H 0.5282 0.1014 0.0125 0.034 Uiso 1 1 calc R . . C3_2 C 0.3301(2) 0.1933(3) 0.07075(12) 0.0329(6) Uani 1 1 d . . . H3C_2 H 0.2658 0.2889 0.0622 0.039 Uiso 1 1 calc R . . H3D_2 H 0.2892 0.1224 0.0529 0.039 Uiso 1 1 calc R . . C4_2 C 0.4862(2) 0.3093(2) -0.04767(12) 0.0290(6) Uani 1 1 d . . . H4_2 H 0.4593 0.4072 -0.0322 0.035 Uiso 1 1 calc R . . C5_2 C 0.6333(2) 0.2985(2) -0.10014(12) 0.0283(6) Uani 1 1 d . . . H5A_2 H 0.6641 0.1997 -0.1129 0.034 Uiso 1 1 calc R . . H5B_2 H 0.6211 0.3653 -0.1495 0.034 Uiso 1 1 calc R . . C6_2 C 0.7542(2) 0.3322(2) -0.06636(12) 0.0291(6) Uani 1 1 d . . . H6_2 H 0.7178 0.4265 -0.0471 0.035 Uiso 1 1 calc R . . C6A_2 C 0.8067(2) 0.2199(3) 0.00093(12) 0.0318(6) Uani 1 1 d . . . H6A_2 H 0.8183 0.1221 -0.0131 0.038 Uiso 1 1 calc R . . C7_2 C 0.9511(3) 0.2338(3) 0.02101(13) 0.0467(7) Uani 1 1 d . . . H7A_2 H 1.0333 0.1766 -0.0095 0.056 Uiso 1 1 calc R . . H7B_2 H 0.9616 0.3357 0.0102 0.056 Uiso 1 1 calc R . . C8_2 C 0.9436(3) 0.1755(3) 0.10766(13) 0.0474(7) Uani 1 1 d . . . H8A_2 H 0.9646 0.0689 0.1172 0.057 Uiso 1 1 calc R . . H8B_2 H 1.0118 0.2108 0.1309 0.057 Uiso 1 1 calc R . . C9_2 C 0.7881(2) 0.2355(3) 0.13963(13) 0.0344(6) Uani 1 1 d . . . H9A_2 H 0.7563 0.1766 0.1895 0.041 Uiso 1 1 calc R . . H9B_2 H 0.7766 0.3361 0.1480 0.041 Uiso 1 1 calc R . . C10_2 C 0.7036(2) 0.2280(2) 0.07741(12) 0.0264(5) Uani 1 1 d . . . C11_2 C 0.5643(2) 0.2230(2) 0.08800(12) 0.0262(5) Uani 1 1 d . . . O12_2 O 0.27054(19) 0.38829(18) -0.10716(10) 0.0473(5) Uani 1 1 d . . . C12_2 C 0.3749(2) 0.2973(3) -0.09430(12) 0.0289(6) Uani 1 1 d . . . O13_2 O 0.40534(16) 0.17139(18) -0.12072(9) 0.0405(4) Uani 1 1 d . . . C13_2 C 0.3080(3) 0.1511(3) -0.16868(15) 0.0453(7) Uani 1 1 d . . . H13D_2 H 0.3354 0.0528 -0.1807 0.068 Uiso 1 1 calc R . . H13E_2 H 0.3135 0.2200 -0.2172 0.068 Uiso 1 1 calc R . . H13F_2 H 0.2092 0.1668 -0.1406 0.068 Uiso 1 1 calc R . . O14_2 O 0.88608(16) 0.48838(17) -0.15435(8) 0.0366(4) Uani 1 1 d . . . C14_2 C 0.9906(3) 0.5203(3) -0.22214(14) 0.0447(7) Uani 1 1 d . . . H14D_2 H 0.9873 0.6243 -0.2337 0.067 Uiso 1 1 calc R . . H14E_2 H 0.9682 0.4882 -0.2668 0.067 Uiso 1 1 calc R . . H14F_2 H 1.0873 0.4700 -0.2119 0.067 Uiso 1 1 calc R . . O15_2 O 0.94931(17) 0.25444(18) -0.16607(9) 0.0397(4) Uani 1 1 d . . . C15_2 C 0.8750(2) 0.3506(3) -0.13337(13) 0.0289(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1_1 0.0415(15) 0.0363(15) 0.0260(13) -0.0053(11) -0.0037(11) -0.0112(11) C2_1 0.0747(19) 0.0328(16) 0.0319(15) -0.0085(12) -0.0044(13) -0.0117(13) C3A_1 0.0385(14) 0.0263(13) 0.0262(13) -0.0036(11) -0.0042(11) -0.0064(11) C3_1 0.082(2) 0.0300(15) 0.0308(15) -0.0050(11) -0.0012(13) -0.0164(14) C4_1 0.0308(13) 0.0281(13) 0.0249(13) -0.0004(11) -0.0064(10) -0.0078(10) C5_1 0.0323(14) 0.0305(14) 0.0244(12) -0.0043(11) -0.0014(10) -0.0067(11) C6A_1 0.0273(13) 0.0250(13) 0.0305(13) -0.0024(10) -0.0044(10) -0.0069(10) C6_1 0.0284(13) 0.0265(13) 0.0310(13) -0.0048(11) -0.0055(10) -0.0056(10) C7_1 0.0370(14) 0.0262(14) 0.0399(15) -0.0027(11) -0.0054(11) -0.0086(11) C8_1 0.0406(15) 0.0299(14) 0.0380(15) 0.0052(11) -0.0015(12) -0.0085(12) C9_1 0.0407(15) 0.0336(14) 0.0295(14) 0.0005(11) -0.0033(11) -0.0068(12) C10_1 0.0237(13) 0.0273(15) 0.0248(13) -0.0017(11) -0.0030(9) -0.0044(10) C11_1 0.0259(13) 0.0297(15) 0.0222(13) -0.0028(11) -0.0037(10) -0.0054(10) O12_1 0.0362(10) 0.0402(10) 0.0383(10) 0.0053(8) -0.0116(8) -0.0092(8) C12_1 0.0310(16) 0.0295(14) 0.0255(13) -0.0075(11) -0.0040(12) -0.0061(12) O13_1 0.0316(11) 0.0367(10) 0.0330(9) 0.0056(8) -0.0047(7) -0.0113(7) C13_1 0.0369(15) 0.0366(15) 0.0366(14) 0.0042(12) 0.0009(11) -0.0148(12) O14_1 0.0452(12) 0.0446(11) 0.0626(12) -0.0308(9) -0.0227(9) 0.0045(8) C14_1 0.0632(19) 0.0516(18) 0.0654(19) -0.0298(15) -0.0253(15) -0.0066(14) O15_1 0.0454(13) 0.0839(16) 0.139(2) -0.0801(16) -0.0279(12) 0.0186(12) C15_1 0.0303(16) 0.0327(15) 0.0380(15) -0.0116(12) -0.0018(12) -0.0057(13) C1_2 0.0330(14) 0.0472(15) 0.0272(13) -0.0063(11) -0.0009(11) -0.0114(12) C2_2 0.0291(14) 0.0496(16) 0.0324(14) -0.0026(12) 0.0032(11) -0.0106(12) C3A_2 0.0258(13) 0.0311(14) 0.0273(13) -0.0036(11) -0.0026(10) -0.0067(10) C3_2 0.0261(13) 0.0408(15) 0.0315(14) -0.0039(11) -0.0010(10) -0.0105(11) C4_2 0.0251(13) 0.0323(14) 0.0296(13) -0.0049(11) -0.0028(11) -0.0069(10) C5_2 0.0271(13) 0.0318(13) 0.0250(13) -0.0006(10) -0.0042(10) -0.0068(10) C6_2 0.0267(13) 0.0352(14) 0.0264(13) -0.0078(11) 0.0001(11) -0.0093(11) C6A_2 0.0278(14) 0.0391(14) 0.0288(14) -0.0062(11) -0.0045(11) -0.0062(11) C7_2 0.0267(14) 0.081(2) 0.0328(15) -0.0080(14) -0.0039(11) -0.0137(13) C8_2 0.0330(16) 0.0734(19) 0.0375(15) -0.0086(14) -0.0104(12) -0.0104(13) C9_2 0.0345(15) 0.0438(15) 0.0274(13) -0.0034(11) -0.0063(11) -0.0137(12) C10_2 0.0283(15) 0.0265(13) 0.0244(13) -0.0027(10) -0.0047(11) -0.0061(10) C11_2 0.0281(15) 0.0279(13) 0.0222(13) -0.0024(10) -0.0025(10) -0.0071(10) O12_2 0.0383(11) 0.0404(11) 0.0630(12) -0.0048(9) -0.0211(9) 0.0007(9) C12_2 0.0246(15) 0.0340(16) 0.0257(13) 0.0009(11) -0.0006(11) -0.0087(13) O13_2 0.0356(10) 0.0427(11) 0.0487(10) -0.0152(9) -0.0211(8) 0.0000(8) C13_2 0.0461(16) 0.0480(16) 0.0488(16) -0.0085(13) -0.0230(13) -0.0100(13) O14_2 0.0358(10) 0.0377(11) 0.0337(9) -0.0042(8) 0.0063(7) -0.0127(8) C14_2 0.0383(15) 0.0551(17) 0.0360(15) 0.0022(13) 0.0087(12) -0.0196(13) O15_2 0.0346(10) 0.0428(11) 0.0412(10) -0.0133(9) 0.0034(8) -0.0084(8) C15_2 0.0248(14) 0.0378(17) 0.0270(13) -0.0079(12) -0.0061(11) -0.0081(12) _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_1 C11_1 1.516(3) . ? C1_1 C2_1 1.523(3) . ? C1_1 H1A_1 0.9900 . ? C1_1 H1B_1 0.9900 . ? C2_1 C3_1 1.525(3) . ? C2_1 H2A_1 0.9900 . ? C2_1 H2B_1 0.9900 . ? C3A_1 C11_1 1.527(3) . ? C3A_1 C4_1 1.529(3) . ? C3A_1 C3_1 1.535(3) . ? C3A_1 H3A_1 1.0000 . ? C3_1 H3B_1 0.9900 . ? C3_1 H3C_1 0.9900 . ? C4_1 C12_1 1.512(3) . ? C4_1 C5_1 1.527(3) . ? C4_1 H4_1 1.0000 . ? C5_1 C6_1 1.534(3) . ? C5_1 H5A_1 0.9900 . ? C5_1 H5B_1 0.9900 . ? C6A_1 C10_1 1.524(3) . ? C6A_1 C6_1 1.531(3) . ? C6A_1 C7_1 1.545(3) . ? C6A_1 H6A_1 1.0000 . ? C6_1 C15_1 1.504(3) . ? C6_1 H6_1 1.0000 . ? C7_1 C8_1 1.525(3) . ? C7_1 H7A_1 0.9900 . ? C7_1 H7B_1 0.9900 . ? C8_1 C9_1 1.516(3) . ? C8_1 H8A_1 0.9900 . ? C8_1 H8B_1 0.9900 . ? C9_1 C10_1 1.516(3) . ? C9_1 H9A_1 0.9900 . ? C9_1 H9B_1 0.9900 . ? C10_1 C11_1 1.325(3) . ? O12_1 C12_1 1.205(3) . ? C12_1 O13_1 1.337(3) . ? O13_1 C13_1 1.448(3) . ? C13_1 H13A_1 0.9800 . ? C13_1 H13B_1 0.9800 . ? C13_1 H13C_1 0.9800 . ? O14_1 C15_1 1.324(3) . ? O14_1 C14_1 1.442(3) . ? C14_1 H14A_1 0.9800 . ? C14_1 H14B_1 0.9800 . ? C14_1 H14C_1 0.9800 . ? O15_1 C15_1 1.188(3) . ? C1_2 C11_2 1.508(3) . ? C1_2 C2_2 1.523(3) . ? C1_2 H1A_2 0.9900 . ? C1_2 H1B_2 0.9900 . ? C2_2 C3_2 1.526(3) . ? C2_2 H2A_2 0.9900 . ? C2_2 H2B_2 0.9900 . ? C3A_2 C11_2 1.526(3) . ? C3A_2 C4_2 1.531(3) . ? C3A_2 C3_2 1.543(3) . ? C3A_2 H3A_2 1.0000 . ? C3_2 H3C_2 0.9900 . ? C3_2 H3D_2 0.9900 . ? C4_2 C12_2 1.510(3) . ? C4_2 C5_2 1.534(3) . ? C4_2 H4_2 1.0000 . ? C5_2 C6_2 1.529(3) . ? C5_2 H5A_2 0.9900 . ? C5_2 H5B_2 0.9900 . ? C6_2 C15_2 1.511(3) . ? C6_2 C6A_2 1.526(3) . ? C6_2 H6_2 1.0000 . ? C6A_2 C10_2 1.524(3) . ? C6A_2 C7_2 1.541(3) . ? C6A_2 H6A_2 1.0000 . ? C7_2 C8_2 1.523(3) . ? C7_2 H7A_2 0.9900 . ? C7_2 H7B_2 0.9900 . ? C8_2 C9_2 1.520(3) . ? C8_2 H8A_2 0.9900 . ? C8_2 H8B_2 0.9900 . ? C9_2 C10_2 1.512(3) . ? C9_2 H9A_2 0.9900 . ? C9_2 H9B_2 0.9900 . ? C10_2 C11_2 1.331(3) . ? O12_2 C12_2 1.201(3) . ? C12_2 O13_2 1.339(3) . ? O13_2 C13_2 1.447(3) . ? C13_2 H13D_2 0.9800 . ? C13_2 H13E_2 0.9800 . ? C13_2 H13F_2 0.9800 . ? O14_2 C15_2 1.334(3) . ? O14_2 C14_2 1.446(3) . ? C14_2 H14D_2 0.9800 . ? C14_2 H14E_2 0.9800 . ? C14_2 H14F_2 0.9800 . ? O15_2 C15_2 1.209(3) . ? 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 C11_1 C1_1 C2_1 104.04(18) . . ? C11_1 C1_1 H1A_1 110.9 . . ? C2_1 C1_1 H1A_1 110.9 . . ? C11_1 C1_1 H1B_1 110.9 . . ? C2_1 C1_1 H1B_1 110.9 . . ? H1A_1 C1_1 H1B_1 109.0 . . ? C1_1 C2_1 C3_1 102.60(19) . . ? C1_1 C2_1 H2A_1 111.2 . . ? C3_1 C2_1 H2A_1 111.2 . . ? C1_1 C2_1 H2B_1 111.2 . . ? C3_1 C2_1 H2B_1 111.2 . . ? H2A_1 C2_1 H2B_1 109.2 . . ? C11_1 C3A_1 C4_1 113.13(18) . . ? C11_1 C3A_1 C3_1 104.09(18) . . ? C4_1 C3A_1 C3_1 113.47(19) . . ? C11_1 C3A_1 H3A_1 108.6 . . ? C4_1 C3A_1 H3A_1 108.6 . . ? C3_1 C3A_1 H3A_1 108.6 . . ? C2_1 C3_1 C3A_1 104.52(19) . . ? C2_1 C3_1 H3B_1 110.8 . . ? C3A_1 C3_1 H3B_1 110.8 . . ? C2_1 C3_1 H3C_1 110.8 . . ? C3A_1 C3_1 H3C_1 110.8 . . ? H3B_1 C3_1 H3C_1 108.9 . . ? C12_1 C4_1 C5_1 107.05(17) . . ? C12_1 C4_1 C3A_1 110.56(18) . . ? C5_1 C4_1 C3A_1 114.47(18) . . ? C12_1 C4_1 H4_1 108.2 . . ? C5_1 C4_1 H4_1 108.2 . . ? C3A_1 C4_1 H4_1 108.2 . . ? C4_1 C5_1 C6_1 115.88(17) . . ? C4_1 C5_1 H5A_1 108.3 . . ? C6_1 C5_1 H5A_1 108.3 . . ? C4_1 C5_1 H5B_1 108.3 . . ? C6_1 C5_1 H5B_1 108.3 . . ? H5A_1 C5_1 H5B_1 107.4 . . ? C10_1 C6A_1 C6_1 115.89(17) . . ? C10_1 C6A_1 C7_1 104.29(17) . . ? C6_1 C6A_1 C7_1 112.63(18) . . ? C10_1 C6A_1 H6A_1 107.9 . . ? C6_1 C6A_1 H6A_1 107.9 . . ? C7_1 C6A_1 H6A_1 107.9 . . ? C15_1 C6_1 C6A_1 111.19(18) . . ? C15_1 C6_1 C5_1 107.60(17) . . ? C6A_1 C6_1 C5_1 114.81(18) . . ? C15_1 C6_1 H6_1 107.7 . . ? C6A_1 C6_1 H6_1 107.7 . . ? C5_1 C6_1 H6_1 107.7 . . ? C8_1 C7_1 C6A_1 105.15(18) . . ? C8_1 C7_1 H7A_1 110.7 . . ? C6A_1 C7_1 H7A_1 110.7 . . ? C8_1 C7_1 H7B_1 110.7 . . ? C6A_1 C7_1 H7B_1 110.7 . . ? H7A_1 C7_1 H7B_1 108.8 . . ? C9_1 C8_1 C7_1 103.36(18) . . ? C9_1 C8_1 H8A_1 111.1 . . ? C7_1 C8_1 H8A_1 111.1 . . ? C9_1 C8_1 H8B_1 111.1 . . ? C7_1 C8_1 H8B_1 111.1 . . ? H8A_1 C8_1 H8B_1 109.1 . . ? C10_1 C9_1 C8_1 104.45(18) . . ? C10_1 C9_1 H9A_1 110.9 . . ? C8_1 C9_1 H9A_1 110.9 . . ? C10_1 C9_1 H9B_1 110.9 . . ? C8_1 C9_1 H9B_1 110.9 . . ? H9A_1 C9_1 H9B_1 108.9 . . ? C11_1 C10_1 C9_1 125.4(2) . . ? C11_1 C10_1 C6A_1 126.00(19) . . ? C9_1 C10_1 C6A_1 108.45(18) . . ? C10_1 C11_1 C1_1 125.88(19) . . ? C10_1 C11_1 C3A_1 125.84(19) . . ? C1_1 C11_1 C3A_1 108.27(18) . . ? O12_1 C12_1 O13_1 123.4(2) . . ? O12_1 C12_1 C4_1 125.2(2) . . ? O13_1 C12_1 C4_1 111.42(19) . . ? C12_1 O13_1 C13_1 116.06(17) . . ? O13_1 C13_1 H13A_1 109.5 . . ? O13_1 C13_1 H13B_1 109.5 . . ? H13A_1 C13_1 H13B_1 109.5 . . ? O13_1 C13_1 H13C_1 109.5 . . ? H13A_1 C13_1 H13C_1 109.5 . . ? H13B_1 C13_1 H13C_1 109.5 . . ? C15_1 O14_1 C14_1 117.83(19) . . ? O14_1 C14_1 H14A_1 109.5 . . ? O14_1 C14_1 H14B_1 109.5 . . ? H14A_1 C14_1 H14B_1 109.5 . . ? O14_1 C14_1 H14C_1 109.5 . . ? H14A_1 C14_1 H14C_1 109.5 . . ? H14B_1 C14_1 H14C_1 109.5 . . ? O15_1 C15_1 O14_1 122.2(2) . . ? O15_1 C15_1 C6_1 125.3(2) . . ? O14_1 C15_1 C6_1 112.4(2) . . ? C11_2 C1_2 C2_2 104.45(18) . . ? C11_2 C1_2 H1A_2 110.9 . . ? C2_2 C1_2 H1A_2 110.9 . . ? C11_2 C1_2 H1B_2 110.9 . . ? C2_2 C1_2 H1B_2 110.9 . . ? H1A_2 C1_2 H1B_2 108.9 . . ? C1_2 C2_2 C3_2 102.79(18) . . ? C1_2 C2_2 H2A_2 111.2 . . ? C3_2 C2_2 H2A_2 111.2 . . ? C1_2 C2_2 H2B_2 111.2 . . ? C3_2 C2_2 H2B_2 111.2 . . ? H2A_2 C2_2 H2B_2 109.1 . . ? C11_2 C3A_2 C4_2 115.18(17) . . ? C11_2 C3A_2 C3_2 104.23(17) . . ? C4_2 C3A_2 C3_2 113.04(17) . . ? C11_2 C3A_2 H3A_2 108.0 . . ? C4_2 C3A_2 H3A_2 108.0 . . ? C3_2 C3A_2 H3A_2 108.0 . . ? C2_2 C3_2 C3A_2 105.02(17) . . ? C2_2 C3_2 H3C_2 110.7 . . ? C3A_2 C3_2 H3C_2 110.7 . . ? C2_2 C3_2 H3D_2 110.7 . . ? C3A_2 C3_2 H3D_2 110.7 . . ? H3C_2 C3_2 H3D_2 108.8 . . ? C12_2 C4_2 C3A_2 110.41(17) . . ? C12_2 C4_2 C5_2 108.86(17) . . ? C3A_2 C4_2 C5_2 114.37(18) . . ? C12_2 C4_2 H4_2 107.7 . . ? C3A_2 C4_2 H4_2 107.7 . . ? C5_2 C4_2 H4_2 107.7 . . ? C6_2 C5_2 C4_2 115.89(18) . . ? C6_2 C5_2 H5A_2 108.3 . . ? C4_2 C5_2 H5A_2 108.3 . . ? C6_2 C5_2 H5B_2 108.3 . . ? C4_2 C5_2 H5B_2 108.3 . . ? H5A_2 C5_2 H5B_2 107.4 . . ? C15_2 C6_2 C6A_2 111.48(18) . . ? C15_2 C6_2 C5_2 106.41(17) . . ? C6A_2 C6_2 C5_2 114.57(18) . . ? C15_2 C6_2 H6_2 108.1 . . ? C6A_2 C6_2 H6_2 108.1 . . ? C5_2 C6_2 H6_2 108.1 . . ? C10_2 C6A_2 C6_2 113.25(18) . . ? C10_2 C6A_2 C7_2 103.86(17) . . ? C6_2 C6A_2 C7_2 114.06(19) . . ? C10_2 C6A_2 H6A_2 108.5 . . ? C6_2 C6A_2 H6A_2 108.5 . . ? C7_2 C6A_2 H6A_2 108.5 . . ? C8_2 C7_2 C6A_2 104.60(19) . . ? C8_2 C7_2 H7A_2 110.8 . . ? C6A_2 C7_2 H7A_2 110.8 . . ? C8_2 C7_2 H7B_2 110.8 . . ? C6A_2 C7_2 H7B_2 110.8 . . ? H7A_2 C7_2 H7B_2 108.9 . . ? C9_2 C8_2 C7_2 102.48(19) . . ? C9_2 C8_2 H8A_2 111.3 . . ? C7_2 C8_2 H8A_2 111.3 . . ? C9_2 C8_2 H8B_2 111.3 . . ? C7_2 C8_2 H8B_2 111.3 . . ? H8A_2 C8_2 H8B_2 109.2 . . ? C10_2 C9_2 C8_2 104.23(18) . . ? C10_2 C9_2 H9A_2 110.9 . . ? C8_2 C9_2 H9A_2 110.9 . . ? C10_2 C9_2 H9B_2 110.9 . . ? C8_2 C9_2 H9B_2 110.9 . . ? H9A_2 C9_2 H9B_2 108.9 . . ? C11_2 C10_2 C9_2 126.01(19) . . ? C11_2 C10_2 C6A_2 125.57(19) . . ? C9_2 C10_2 C6A_2 108.36(18) . . ? C10_2 C11_2 C1_2 125.83(19) . . ? C10_2 C11_2 C3A_2 125.59(19) . . ? C1_2 C11_2 C3A_2 108.39(18) . . ? O12_2 C12_2 O13_2 122.7(2) . . ? O12_2 C12_2 C4_2 125.2(2) . . ? O13_2 C12_2 C4_2 112.1(2) . . ? C12_2 O13_2 C13_2 116.51(18) . . ? O13_2 C13_2 H13D_2 109.5 . . ? O13_2 C13_2 H13E_2 109.5 . . ? H13D_2 C13_2 H13E_2 109.5 . . ? O13_2 C13_2 H13F_2 109.5 . . ? H13D_2 C13_2 H13F_2 109.5 . . ? H13E_2 C13_2 H13F_2 109.5 . . ? C15_2 O14_2 C14_2 116.11(18) . . ? O14_2 C14_2 H14D_2 109.5 . . ? O14_2 C14_2 H14E_2 109.5 . . ? H14D_2 C14_2 H14E_2 109.5 . . ? O14_2 C14_2 H14F_2 109.5 . . ? H14D_2 C14_2 H14F_2 109.5 . . ? H14E_2 C14_2 H14F_2 109.5 . . ? O15_2 C15_2 O14_2 123.8(2) . . ? O15_2 C15_2 C6_2 124.9(2) . . ? O14_2 C15_2 C6_2 111.3(2) . . ? 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 C11_1 C1_1 C2_1 C3_1 -37.1(2) . . . . ? C1_1 C2_1 C3_1 C3A_1 40.4(3) . . . . ? C11_1 C3A_1 C3_1 C2_1 -27.5(3) . . . . ? C4_1 C3A_1 C3_1 C2_1 -150.9(2) . . . . ? C11_1 C3A_1 C4_1 C12_1 -162.83(18) . . . . ? C3_1 C3A_1 C4_1 C12_1 -44.5(3) . . . . ? C11_1 C3A_1 C4_1 C5_1 76.2(2) . . . . ? C3_1 C3A_1 C4_1 C5_1 -165.51(19) . . . . ? C12_1 C4_1 C5_1 C6_1 166.37(18) . . . . ? C3A_1 C4_1 C5_1 C6_1 -70.7(2) . . . . ? C10_1 C6A_1 C6_1 C15_1 168.63(19) . . . . ? C7_1 C6A_1 C6_1 C15_1 48.7(2) . . . . ? C10_1 C6A_1 C6_1 C5_1 -68.9(2) . . . . ? C7_1 C6A_1 C6_1 C5_1 171.11(18) . . . . ? C4_1 C5_1 C6_1 C15_1 -171.12(19) . . . . ? C4_1 C5_1 C6_1 C6A_1 64.5(3) . . . . ? C10_1 C6A_1 C7_1 C8_1 23.7(2) . . . . ? C6_1 C6A_1 C7_1 C8_1 150.11(19) . . . . ? C6A_1 C7_1 C8_1 C9_1 -37.1(2) . . . . ? C7_1 C8_1 C9_1 C10_1 35.8(2) . . . . ? C8_1 C9_1 C10_1 C11_1 154.5(2) . . . . ? C8_1 C9_1 C10_1 C6A_1 -21.4(2) . . . . ? C6_1 C6A_1 C10_1 C11_1 58.3(3) . . . . ? C7_1 C6A_1 C10_1 C11_1 -177.3(2) . . . . ? C6_1 C6A_1 C10_1 C9_1 -125.8(2) . . . . ? C7_1 C6A_1 C10_1 C9_1 -1.4(2) . . . . ? C9_1 C10_1 C11_1 C1_1 -1.9(3) . . . . ? C6A_1 C10_1 C11_1 C1_1 173.4(2) . . . . ? C9_1 C10_1 C11_1 C3A_1 179.3(2) . . . . ? C6A_1 C10_1 C11_1 C3A_1 -5.5(3) . . . . ? C2_1 C1_1 C11_1 C10_1 -158.6(2) . . . . ? C2_1 C1_1 C11_1 C3A_1 20.4(2) . . . . ? C4_1 C3A_1 C11_1 C10_1 -53.0(3) . . . . ? C3_1 C3A_1 C11_1 C10_1 -176.6(2) . . . . ? C4_1 C3A_1 C11_1 C1_1 128.0(2) . . . . ? C3_1 C3A_1 C11_1 C1_1 4.3(2) . . . . ? C5_1 C4_1 C12_1 O12_1 68.2(3) . . . . ? C3A_1 C4_1 C12_1 O12_1 -57.1(3) . . . . ? C5_1 C4_1 C12_1 O13_1 -109.7(2) . . . . ? C3A_1 C4_1 C12_1 O13_1 124.97(19) . . . . ? O12_1 C12_1 O13_1 C13_1 0.0(3) . . . . ? C4_1 C12_1 O13_1 C13_1 177.99(18) . . . . ? C14_1 O14_1 C15_1 O15_1 -3.0(4) . . . . ? C14_1 O14_1 C15_1 C6_1 176.9(2) . . . . ? C6A_1 C6_1 C15_1 O15_1 -121.0(3) . . . . ? C5_1 C6_1 C15_1 O15_1 112.4(3) . . . . ? C6A_1 C6_1 C15_1 O14_1 59.0(2) . . . . ? C5_1 C6_1 C15_1 O14_1 -67.5(2) . . . . ? C11_2 C1_2 C2_2 C3_2 -36.7(2) . . . . ? C1_2 C2_2 C3_2 C3A_2 38.0(2) . . . . ? C11_2 C3A_2 C3_2 C2_2 -24.4(2) . . . . ? C4_2 C3A_2 C3_2 C2_2 -150.18(19) . . . . ? C11_2 C3A_2 C4_2 C12_2 -165.88(19) . . . . ? C3_2 C3A_2 C4_2 C12_2 -46.2(3) . . . . ? C11_2 C3A_2 C4_2 C5_2 70.9(2) . . . . ? C3_2 C3A_2 C4_2 C5_2 -169.38(18) . . . . ? C12_2 C4_2 C5_2 C6_2 170.72(19) . . . . ? C3A_2 C4_2 C5_2 C6_2 -65.3(3) . . . . ? C4_2 C5_2 C6_2 C15_2 -166.53(19) . . . . ? C4_2 C5_2 C6_2 C6A_2 69.8(2) . . . . ? C15_2 C6_2 C6A_2 C10_2 163.17(19) . . . . ? C5_2 C6_2 C6A_2 C10_2 -75.9(2) . . . . ? C15_2 C6_2 C6A_2 C7_2 44.7(3) . . . . ? C5_2 C6_2 C6A_2 C7_2 165.57(19) . . . . ? C10_2 C6A_2 C7_2 C8_2 27.2(3) . . . . ? C6_2 C6A_2 C7_2 C8_2 150.9(2) . . . . ? C6A_2 C7_2 C8_2 C9_2 -40.2(3) . . . . ? C7_2 C8_2 C9_2 C10_2 37.3(2) . . . . ? C8_2 C9_2 C10_2 C11_2 156.5(2) . . . . ? C8_2 C9_2 C10_2 C6A_2 -20.9(2) . . . . ? C6_2 C6A_2 C10_2 C11_2 54.5(3) . . . . ? C7_2 C6A_2 C10_2 C11_2 178.8(2) . . . . ? C6_2 C6A_2 C10_2 C9_2 -128.1(2) . . . . ? C7_2 C6A_2 C10_2 C9_2 -3.9(2) . . . . ? C9_2 C10_2 C11_2 C1_2 1.6(4) . . . . ? C6A_2 C10_2 C11_2 C1_2 178.5(2) . . . . ? C9_2 C10_2 C11_2 C3A_2 -172.7(2) . . . . ? C6A_2 C10_2 C11_2 C3A_2 4.2(3) . . . . ? C2_2 C1_2 C11_2 C10_2 -153.1(2) . . . . ? C2_2 C1_2 C11_2 C3A_2 22.0(2) . . . . ? C4_2 C3A_2 C11_2 C10_2 -59.0(3) . . . . ? C3_2 C3A_2 C11_2 C10_2 176.6(2) . . . . ? C4_2 C3A_2 C11_2 C1_2 125.88(19) . . . . ? C3_2 C3A_2 C11_2 C1_2 1.4(2) . . . . ? C3A_2 C4_2 C12_2 O12_2 114.6(2) . . . . ? C5_2 C4_2 C12_2 O12_2 -119.1(2) . . . . ? C3A_2 C4_2 C12_2 O13_2 -65.5(2) . . . . ? C5_2 C4_2 C12_2 O13_2 60.8(2) . . . . ? O12_2 C12_2 O13_2 C13_2 2.1(3) . . . . ? C4_2 C12_2 O13_2 C13_2 -177.77(18) . . . . ? C14_2 O14_2 C15_2 O15_2 2.4(3) . . . . ? C14_2 O14_2 C15_2 C6_2 -175.15(18) . . . . ? C6A_2 C6_2 C15_2 O15_2 55.7(3) . . . . ? C5_2 C6_2 C15_2 O15_2 -69.9(3) . . . . ? C6A_2 C6_2 C15_2 O14_2 -126.9(2) . . . . ? C5_2 C6_2 C15_2 O14_2 107.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 20.39 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.193 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.040