# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_p21n _database_code_depnum_ccdc_archive 'CCDC 912716' #TrackingRef '9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 O2' _chemical_formula_weight 266.32 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 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 8.517(6) _cell_length_b 10.598(7) _cell_length_c 16.662(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.570(7) _cell_angle_gamma 90.00 _cell_volume 1499.3(17) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2074 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 21.33 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9843 _exptl_absorpt_correction_T_max 0.9888 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6977 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2770 _reflns_number_gt 1517 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+0.0000P] 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_number_reflns 2770 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0985 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0964(2) 0.4041(2) 0.92319(13) 0.0616(6) Uani 1 1 d . . . C2 C 1.0630(3) 0.2703(2) 0.94364(12) 0.0664(6) Uani 1 1 d . . . H2 H 0.9638 0.2681 0.9696 0.080 Uiso 1 1 calc R . . C3 C 1.0354(2) 0.20904(18) 0.86170(12) 0.0559(6) Uani 1 1 d . . . H3 H 1.1387 0.1870 0.8438 0.067 Uiso 1 1 calc R . . C4 C 0.9682(2) 0.31862(16) 0.80740(11) 0.0459(5) Uani 1 1 d . . . C5 C 0.7904(2) 0.32864(17) 0.80400(11) 0.0482(5) Uani 1 1 d . . . C6 C 0.7151(3) 0.3969(2) 0.86057(13) 0.0647(6) Uani 1 1 d . . . H6 H 0.7740 0.4413 0.9006 0.078 Uiso 1 1 calc R . . C7 C 0.5516(3) 0.3992(2) 0.85755(16) 0.0804(7) Uani 1 1 d . . . H7 H 0.5020 0.4442 0.8962 0.096 Uiso 1 1 calc R . . C8 C 0.4633(3) 0.3367(3) 0.79886(19) 0.0860(8) Uani 1 1 d . . . H8 H 0.3539 0.3395 0.7970 0.103 Uiso 1 1 calc R . . C9 C 0.5364(3) 0.2694(2) 0.74248(15) 0.0770(7) Uani 1 1 d . . . H9 H 0.4765 0.2265 0.7021 0.092 Uiso 1 1 calc R . . C10 C 0.6981(2) 0.2652(2) 0.74518(13) 0.0628(6) Uani 1 1 d . . . H10 H 0.7463 0.2187 0.7067 0.075 Uiso 1 1 calc R . . C11 C 1.0266(2) 0.32379(19) 0.72366(11) 0.0489(5) Uani 1 1 d . . . C12 C 1.0901(2) 0.2225(2) 0.68691(13) 0.0674(6) Uani 1 1 d . . . H12 H 1.0992 0.1455 0.7137 0.081 Uiso 1 1 calc R . . C13 C 1.1414(3) 0.2332(3) 0.61000(15) 0.0853(8) Uani 1 1 d . . . H13 H 1.1826 0.1633 0.5852 0.102 Uiso 1 1 calc R . . C14 C 1.1312(3) 0.3456(4) 0.57123(16) 0.0939(9) Uani 1 1 d . . . H14 H 1.1675 0.3531 0.5203 0.113 Uiso 1 1 calc R . . C15 C 1.0681(3) 0.4475(3) 0.60647(16) 0.0927(8) Uani 1 1 d . . . H15 H 1.0604 0.5244 0.5795 0.111 Uiso 1 1 calc R . . C16 C 1.0156(3) 0.4363(2) 0.68221(13) 0.0701(7) Uani 1 1 d . . . H16 H 0.9719 0.5061 0.7059 0.084 Uiso 1 1 calc R . . C17 C 1.1904(3) 0.2127(3) 1.00108(16) 0.1148(10) Uani 1 1 d . . . H17A H 1.1984 0.2593 1.0506 0.172 Uiso 1 1 calc R . . H17B H 1.2894 0.2158 0.9773 0.172 Uiso 1 1 calc R . . H17C H 1.1642 0.1265 1.0116 0.172 Uiso 1 1 calc R . . C18 C 0.9380(3) 0.0887(2) 0.86049(14) 0.0783(7) Uani 1 1 d . . . H18A H 0.8387 0.1057 0.8818 0.117 Uiso 1 1 calc R . . H18B H 0.9935 0.0255 0.8928 0.117 Uiso 1 1 calc R . . H18C H 0.9201 0.0589 0.8061 0.117 Uiso 1 1 calc R . . O1 O 1.03635(15) 0.43086(12) 0.84808(8) 0.0563(4) Uani 1 1 d . . . O2 O 1.16663(19) 0.48255(17) 0.96322(9) 0.0907(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 0.0510(13) 0.0842(18) 0.0499(14) -0.0124(13) 0.0060(10) -0.0120(12) C2 0.0654(14) 0.0836(17) 0.0498(13) 0.0075(12) 0.0020(10) -0.0044(12) C3 0.0576(13) 0.0558(13) 0.0544(13) 0.0041(11) 0.0050(9) 0.0023(10) C4 0.0485(11) 0.0411(11) 0.0475(11) -0.0050(9) 0.0001(9) -0.0059(9) C5 0.0479(11) 0.0464(12) 0.0499(12) 0.0011(10) 0.0023(9) -0.0020(9) C6 0.0599(14) 0.0710(15) 0.0634(14) -0.0044(12) 0.0059(11) 0.0050(11) C7 0.0620(16) 0.094(2) 0.0875(18) 0.0056(16) 0.0207(14) 0.0139(14) C8 0.0475(14) 0.104(2) 0.107(2) 0.0212(18) 0.0089(15) -0.0007(14) C9 0.0571(15) 0.0848(18) 0.0866(18) 0.0086(15) -0.0096(13) -0.0178(13) C10 0.0549(14) 0.0671(15) 0.0654(14) -0.0030(12) -0.0009(10) -0.0102(11) C11 0.0435(11) 0.0539(13) 0.0488(12) -0.0014(11) 0.0007(9) -0.0010(9) C12 0.0727(15) 0.0695(15) 0.0604(14) -0.0040(12) 0.0083(11) 0.0031(12) C13 0.0821(18) 0.107(2) 0.0687(18) -0.0164(17) 0.0169(14) 0.0100(16) C14 0.0841(19) 0.138(3) 0.0622(17) 0.007(2) 0.0218(14) -0.0037(18) C15 0.105(2) 0.104(2) 0.0709(18) 0.0275(17) 0.0184(15) -0.0030(18) C16 0.0813(16) 0.0686(16) 0.0605(15) 0.0102(13) 0.0071(12) 0.0068(12) C17 0.124(2) 0.139(3) 0.0759(19) 0.0157(18) -0.0300(17) 0.015(2) C18 0.0937(18) 0.0535(15) 0.0876(17) 0.0140(13) 0.0075(14) -0.0086(12) O1 0.0620(9) 0.0537(9) 0.0526(9) -0.0051(7) -0.0002(7) -0.0146(7) O2 0.0851(11) 0.1149(14) 0.0711(11) -0.0299(10) 0.0002(9) -0.0384(10) _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 O2 1.196(2) . ? C1 O1 1.344(2) . ? C1 C2 1.491(3) . ? C2 C3 1.513(3) . ? C2 C17 1.517(3) . ? C2 H2 0.9800 . ? C3 C18 1.521(3) . ? C3 C4 1.553(3) . ? C3 H3 0.9800 . ? C4 O1 1.466(2) . ? C4 C5 1.515(3) . ? C4 C11 1.519(3) . ? C5 C10 1.381(3) . ? C5 C6 1.385(3) . ? C6 C7 1.389(3) . ? C6 H6 0.9300 . ? C7 C8 1.358(3) . ? C7 H7 0.9300 . ? C8 C9 1.368(4) . ? C8 H8 0.9300 . ? C9 C10 1.375(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.368(3) . ? C11 C16 1.377(3) . ? C12 C13 1.391(3) . ? C12 H12 0.9300 . ? C13 C14 1.354(4) . ? C13 H13 0.9300 . ? C14 C15 1.361(4) . ? C14 H14 0.9300 . ? C15 C16 1.377(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 O2 C1 O1 120.6(2) . . ? O2 C1 C2 129.0(2) . . ? O1 C1 C2 110.38(19) . . ? C1 C2 C3 102.75(17) . . ? C1 C2 C17 112.8(2) . . ? C3 C2 C17 116.6(2) . . ? C1 C2 H2 108.1 . . ? C3 C2 H2 108.1 . . ? C17 C2 H2 108.1 . . ? C2 C3 C18 114.67(18) . . ? C2 C3 C4 103.20(16) . . ? C18 C3 C4 116.36(17) . . ? C2 C3 H3 107.4 . . ? C18 C3 H3 107.4 . . ? C4 C3 H3 107.4 . . ? O1 C4 C5 108.56(14) . . ? O1 C4 C11 104.40(14) . . ? C5 C4 C11 111.27(15) . . ? O1 C4 C3 102.91(15) . . ? C5 C4 C3 113.27(15) . . ? C11 C4 C3 115.44(16) . . ? C10 C5 C6 117.98(19) . . ? C10 C5 C4 120.19(17) . . ? C6 C5 C4 121.79(18) . . ? C5 C6 C7 120.1(2) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.9(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 119.5(2) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C10 120.3(2) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C5 121.2(2) . . ? C9 C10 H10 119.4 . . ? C5 C10 H10 119.4 . . ? C12 C11 C16 117.91(19) . . ? C12 C11 C4 123.55(18) . . ? C16 C11 C4 118.53(18) . . ? C11 C12 C13 120.8(2) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 119.9(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.3(2) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C16 119.7(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C11 C16 C15 121.4(2) . . ? C11 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C2 C17 H17A 109.5 . . ? C2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C3 C18 H18A 109.5 . . ? C3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C1 O1 C4 111.50(16) . . ? 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 O2 C1 C2 C3 -157.0(2) . . . . ? O1 C1 C2 C3 22.1(2) . . . . ? O2 C1 C2 C17 -30.5(3) . . . . ? O1 C1 C2 C17 148.6(2) . . . . ? C1 C2 C3 C18 -157.04(18) . . . . ? C17 C2 C3 C18 79.1(3) . . . . ? C1 C2 C3 C4 -29.48(19) . . . . ? C17 C2 C3 C4 -153.4(2) . . . . ? C2 C3 C4 O1 27.23(18) . . . . ? C18 C3 C4 O1 153.71(17) . . . . ? C2 C3 C4 C5 -89.78(18) . . . . ? C18 C3 C4 C5 36.7(2) . . . . ? C2 C3 C4 C11 140.28(17) . . . . ? C18 C3 C4 C11 -93.2(2) . . . . ? O1 C4 C5 C10 155.42(17) . . . . ? C11 C4 C5 C10 41.1(2) . . . . ? C3 C4 C5 C10 -90.9(2) . . . . ? O1 C4 C5 C6 -26.9(2) . . . . ? C11 C4 C5 C6 -141.28(19) . . . . ? C3 C4 C5 C6 86.7(2) . . . . ? C10 C5 C6 C7 0.6(3) . . . . ? C4 C5 C6 C7 -177.08(19) . . . . ? C5 C6 C7 C8 -1.0(3) . . . . ? C6 C7 C8 C9 0.7(4) . . . . ? C7 C8 C9 C10 0.0(4) . . . . ? C8 C9 C10 C5 -0.4(3) . . . . ? C6 C5 C10 C9 0.1(3) . . . . ? C4 C5 C10 C9 177.82(19) . . . . ? O1 C4 C11 C12 132.94(19) . . . . ? C5 C4 C11 C12 -110.1(2) . . . . ? C3 C4 C11 C12 20.7(3) . . . . ? O1 C4 C11 C16 -47.0(2) . . . . ? C5 C4 C11 C16 70.0(2) . . . . ? C3 C4 C11 C16 -159.15(17) . . . . ? C16 C11 C12 C13 -0.2(3) . . . . ? C4 C11 C12 C13 179.9(2) . . . . ? C11 C12 C13 C14 1.2(4) . . . . ? C12 C13 C14 C15 -1.3(4) . . . . ? C13 C14 C15 C16 0.5(4) . . . . ? C12 C11 C16 C15 -0.6(3) . . . . ? C4 C11 C16 C15 179.3(2) . . . . ? C14 C15 C16 C11 0.5(4) . . . . ? O2 C1 O1 C4 174.70(18) . . . . ? C2 C1 O1 C4 -4.5(2) . . . . ? C5 C4 O1 C1 105.64(16) . . . . ? C11 C4 O1 C1 -135.58(16) . . . . ? C3 C4 O1 C1 -14.66(18) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.224 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.030 data_zhangjj1026 _database_code_depnum_ccdc_archive 'CCDC 912717' #TrackingRef 'Sacidumlignan A.cif' _audit_creation_date 2012-10-26 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H24 O6' _chemical_formula_sum 'C22 H24 O6' _chemical_formula_weight 384.41 _chemical_melting_point ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.460 0.250 185 23 ' ' 2 0.500 0.540 0.750 185 23 ' ' _platon_squeeze_details ; ; 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' _space_group_crystal_system monoclinic _space_group_IT_number 13 _space_group_name_H-M_alt 'P 1 2/c 1' _space_group_name_Hall '-P 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 '-x, -y, -z' 4 'x, -y, z-1/2' _cell_length_a 12.3947(7) _cell_length_b 8.5143(4) _cell_length_c 21.6771(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.571(6) _cell_angle_gamma 90.00 _cell_volume 2214.1(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1269 _cell_measurement_temperature 294.50(14) _cell_measurement_theta_max 28.4643 _cell_measurement_theta_min 2.9471 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59743 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light orange' _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_unetI/netI 0.1028 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 10782 _diffrn_reflns_theta_full 25.68 _diffrn_reflns_theta_max 25.68 _diffrn_reflns_theta_min 2.95 _diffrn_ambient_temperature 294.50(14) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.9975 _diffrn_measured_fraction_theta_max 0.9753 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -58.00 -31.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -19.3492 118.0000 88.0000 27 #__ type_ start__ end____ width___ exp.time_ 2 omega 54.00 91.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 57.0000 -150.0000 37 #__ type_ start__ end____ width___ exp.time_ 3 omega 4.00 96.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 38.0000 120.0000 92 #__ type_ start__ end____ width___ exp.time_ 4 omega 0.00 33.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 -57.0000 -120.0000 33 #__ type_ start__ end____ width___ exp.time_ 5 omega -8.00 18.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 -77.0000 120.0000 26 #__ type_ start__ end____ width___ exp.time_ 6 omega -8.00 89.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 22.6305 77.0000 -30.0000 97 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0310823000 _diffrn_orient_matrix_UB_12 0.0016093000 _diffrn_orient_matrix_UB_13 0.0233401000 _diffrn_orient_matrix_UB_21 -0.0491103000 _diffrn_orient_matrix_UB_22 0.0168575000 _diffrn_orient_matrix_UB_23 -0.0240597000 _diffrn_orient_matrix_UB_31 -0.0107803000 _diffrn_orient_matrix_UB_32 -0.0815835000 _diffrn_orient_matrix_UB_33 -0.0044776000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1810 _reflns_number_total 4210 _reflns_odcompleteness_completeness 99.75 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.501 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.072 _refine_ls_extinction_coef 0.007(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 4210 _refine_ls_number_restraints 168 _refine_ls_R_factor_all 0.1775 _refine_ls_R_factor_gt 0.0973 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1668P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2672 _refine_ls_wR_factor_ref 0.3319 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 0.1187(4) 0.4492(5) 0.70579(19) 0.0997(14) Uani 1 1 d U . . O2 O 0.1928(4) 0.7389(5) 0.75848(16) 0.0971(14) Uani 1 1 d U . . H2 H 0.1469 0.6827 0.7692 0.146 Uiso 1 1 calc R . . O3 O 0.2681(3) 0.9514(4) 0.69294(15) 0.0799(11) Uani 1 1 d U . . O4 O 0.1284(3) 0.9929(4) 0.33710(14) 0.0681(10) Uani 1 1 d U . . O5 O 0.3420(3) 1.0311(5) 0.34725(18) 0.0919(13) Uani 1 1 d U . . H5 H 0.4101 1.0301 0.3538 0.138 Uiso 1 1 calc R . . O6 O 0.4983(3) 0.8793(5) 0.43309(19) 0.0934(13) Uani 1 1 d U . . C1 C 0.2059(3) 0.5960(5) 0.50807(17) 0.0453(10) Uani 1 1 d U . . C2 C 0.1667(3) 0.4491(5) 0.48217(18) 0.0482(11) Uani 1 1 d U . . C3 C 0.1291(3) 0.3391(5) 0.52012(18) 0.0478(11) Uani 1 1 d U . . C4 C 0.1298(4) 0.3726(5) 0.58123(19) 0.0507(11) Uani 1 1 d U . . H4 H 0.1059 0.2967 0.6057 0.061 Uiso 1 1 calc R . . C5 C 0.1658(3) 0.5199(5) 0.60892(19) 0.0467(10) Uani 1 1 d U . . C6 C 0.1643(4) 0.5585(5) 0.67244(19) 0.0605(12) Uani 1 1 d U . . C7 C 0.1954(4) 0.7031(5) 0.69708(19) 0.0597(12) Uani 1 1 d U . . C8 C 0.2364(4) 0.8150(5) 0.6608(2) 0.0561(12) Uani 1 1 d U . . C9 C 0.2405(4) 0.7819(5) 0.59968(19) 0.0530(11) Uani 1 1 d U . . H9 H 0.2668 0.8570 0.5759 0.064 Uiso 1 1 calc R . . C10 C 0.2048(3) 0.6339(4) 0.57255(17) 0.0440(10) Uani 1 1 d U . . C11 C 0.1674(4) 0.4074(6) 0.4150(2) 0.0702(14) Uani 1 1 d U . . H11A H 0.0954 0.4287 0.3872 0.105 Uiso 1 1 calc R . . H11B H 0.1844 0.2978 0.4128 0.105 Uiso 1 1 calc R . . H11C H 0.2228 0.4689 0.4021 0.105 Uiso 1 1 calc R . . C12 C 0.0862(4) 0.1773(6) 0.4932(2) 0.0695(14) Uani 1 1 d U . . H12A H 0.0219 0.1907 0.4581 0.104 Uiso 1 1 calc R . . H12B H 0.0663 0.1163 0.5259 0.104 Uiso 1 1 calc R . . H12C H 0.1436 0.1240 0.4788 0.104 Uiso 1 1 calc R . . C13 C 0.1824(8) 0.3750(11) 0.7535(3) 0.161(4) Uani 1 1 d U . . H13A H 0.2363 0.3142 0.7389 0.242 Uiso 1 1 calc R . . H13B H 0.1379 0.3064 0.7722 0.242 Uiso 1 1 calc R . . H13C H 0.2202 0.4494 0.7848 0.242 Uiso 1 1 calc R . . C14 C 0.3340(6) 1.0560(6) 0.6671(3) 0.097(2) Uani 1 1 d U . . H14A H 0.2879 1.1080 0.6306 0.146 Uiso 1 1 calc R . . H14B H 0.3915 0.9982 0.6546 0.146 Uiso 1 1 calc R . . H14C H 0.3673 1.1326 0.6986 0.146 Uiso 1 1 calc R . . C15 C 0.2452(3) 0.7126(5) 0.46764(17) 0.0446(10) Uani 1 1 d U . . C16 C 0.1656(3) 0.7972(4) 0.42243(17) 0.0479(11) Uani 1 1 d U . . H16 H 0.0901 0.7822 0.4191 0.058 Uiso 1 1 calc R . . C17 C 0.1996(4) 0.9023(5) 0.38293(18) 0.0543(12) Uani 1 1 d U . . C18 C 0.3099(4) 0.9264(6) 0.3870(2) 0.0621(13) Uani 1 1 d U . . C19 C 0.3900(4) 0.8456(6) 0.4328(2) 0.0642(13) Uani 1 1 d U . . C20 C 0.3558(4) 0.7381(5) 0.4727(2) 0.0560(12) Uani 1 1 d U . . H20 H 0.4090 0.6833 0.5030 0.067 Uiso 1 1 calc R . . C21 C 0.0137(4) 0.9762(6) 0.3311(2) 0.0738(15) Uani 1 1 d U . . H21A H -0.0267 1.0421 0.2971 0.111 Uiso 1 1 calc R . . H21B H -0.0033 1.0064 0.3703 0.111 Uiso 1 1 calc R . . H21C H -0.0075 0.8686 0.3217 0.111 Uiso 1 1 calc R . . C22 C 0.5836(5) 0.8036(8) 0.4798(3) 0.104(2) Uani 1 1 d U . . H22A H 0.5806 0.6925 0.4720 0.156 Uiso 1 1 calc R . . H22B H 0.5729 0.8239 0.5214 0.156 Uiso 1 1 calc R . . H22C H 0.6550 0.8433 0.4774 0.156 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 0.144(4) 0.092(3) 0.065(2) 0.010(2) 0.029(2) -0.032(3) O2 0.160(4) 0.085(3) 0.056(2) -0.011(2) 0.044(2) -0.012(2) O3 0.108(3) 0.063(2) 0.067(2) -0.0193(17) 0.019(2) -0.0156(19) O4 0.060(2) 0.081(2) 0.0610(19) 0.0233(17) 0.0121(16) 0.0031(16) O5 0.079(3) 0.115(3) 0.084(2) 0.044(2) 0.024(2) -0.017(2) O6 0.049(2) 0.123(3) 0.108(3) 0.034(2) 0.0181(19) -0.0084(19) C1 0.045(2) 0.048(2) 0.041(2) 0.0012(18) 0.0074(17) 0.0023(17) C2 0.042(2) 0.054(2) 0.045(2) -0.004(2) 0.0052(18) 0.0017(18) C3 0.051(3) 0.048(2) 0.043(2) -0.0046(19) 0.0095(18) -0.0081(18) C4 0.060(3) 0.041(2) 0.052(2) -0.0024(19) 0.0159(19) -0.0116(18) C5 0.046(2) 0.048(2) 0.046(2) 0.0011(19) 0.0109(17) 0.0017(18) C6 0.085(3) 0.056(3) 0.043(2) 0.000(2) 0.022(2) -0.005(2) C7 0.076(3) 0.064(3) 0.041(2) -0.006(2) 0.018(2) 0.004(2) C8 0.062(3) 0.049(3) 0.053(2) -0.002(2) 0.008(2) -0.0016(19) C9 0.060(3) 0.048(2) 0.048(2) -0.0030(19) 0.008(2) -0.0030(19) C10 0.048(2) 0.043(2) 0.040(2) -0.0007(18) 0.0085(17) -0.0004(17) C11 0.086(4) 0.077(3) 0.048(2) -0.013(2) 0.019(2) -0.006(3) C12 0.075(3) 0.065(3) 0.070(3) -0.018(2) 0.021(2) -0.021(2) C13 0.230(10) 0.155(7) 0.085(5) 0.014(5) 0.013(6) -0.054(7) C14 0.127(6) 0.059(3) 0.104(4) -0.013(3) 0.026(4) -0.026(3) C15 0.044(2) 0.049(2) 0.041(2) -0.0015(18) 0.0105(17) -0.0041(17) C16 0.050(3) 0.050(2) 0.044(2) 0.0038(19) 0.0137(18) 0.0012(18) C17 0.059(3) 0.059(3) 0.041(2) 0.006(2) 0.006(2) 0.003(2) C18 0.061(3) 0.074(3) 0.050(2) 0.015(2) 0.012(2) -0.007(2) C19 0.056(3) 0.075(3) 0.062(3) 0.012(2) 0.017(2) -0.007(2) C20 0.053(3) 0.063(3) 0.052(2) 0.011(2) 0.014(2) 0.001(2) C21 0.067(3) 0.101(4) 0.050(3) 0.009(3) 0.008(2) 0.027(3) C22 0.061(4) 0.129(5) 0.115(5) 0.031(4) 0.006(3) -0.003(3) _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 C6 1.383(6) . ? O1 C13 1.297(8) . ? O2 H2 0.8200 . ? O2 C7 1.374(5) . ? O3 C8 1.360(5) . ? O3 C14 1.415(7) . ? O4 C17 1.385(5) . ? O4 C21 1.402(6) . ? O5 H5 0.8200 . ? O5 C18 1.367(5) . ? O6 C19 1.371(6) . ? O6 C22 1.421(6) . ? C1 C2 1.407(6) . ? C1 C10 1.438(5) . ? C1 C15 1.486(6) . ? C2 C3 1.401(6) . ? C2 C11 1.501(6) . ? C3 C4 1.353(6) . ? C3 C12 1.538(6) . ? C4 H4 0.9300 . ? C4 C5 1.413(5) . ? C5 C6 1.420(6) . ? C5 C10 1.411(5) . ? C6 C7 1.359(6) . ? C7 C8 1.409(6) . ? C8 C9 1.368(6) . ? C9 H9 0.9300 . ? C9 C10 1.414(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.402(5) . ? C15 C20 1.365(6) . ? C16 H16 0.9300 . ? C16 C17 1.376(6) . ? C17 C18 1.363(7) . ? C18 C19 1.396(6) . ? C19 C20 1.396(6) . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 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 C13 O1 C6 119.9(6) . . ? C7 O2 H2 109.5 . . ? C8 O3 C14 117.1(4) . . ? C17 O4 C21 117.3(4) . . ? C18 O5 H5 109.5 . . ? C19 O6 C22 117.4(4) . . ? C2 C1 C10 120.1(4) . . ? C2 C1 C15 119.4(3) . . ? C10 C1 C15 120.6(3) . . ? C1 C2 C11 120.8(4) . . ? C3 C2 C1 119.5(4) . . ? C3 C2 C11 119.7(4) . . ? C2 C3 C12 120.7(4) . . ? C4 C3 C2 120.8(4) . . ? C4 C3 C12 118.5(4) . . ? C3 C4 H4 119.1 . . ? C3 C4 C5 121.8(4) . . ? C5 C4 H4 119.1 . . ? C4 C5 C6 122.5(4) . . ? C10 C5 C4 119.3(4) . . ? C10 C5 C6 118.2(4) . . ? O1 C6 C5 117.2(4) . . ? C7 C6 O1 121.2(4) . . ? C7 C6 C5 121.2(4) . . ? O2 C7 C8 119.4(4) . . ? C6 C7 O2 120.5(4) . . ? C6 C7 C8 120.0(4) . . ? O3 C8 C7 112.9(4) . . ? O3 C8 C9 126.6(4) . . ? C9 C8 C7 120.5(4) . . ? C8 C9 H9 119.9 . . ? C8 C9 C10 120.2(4) . . ? C10 C9 H9 119.9 . . ? C5 C10 C1 118.5(3) . . ? C5 C10 C9 119.8(4) . . ? C9 C10 C1 121.7(4) . . ? C2 C11 H11A 109.5 . . ? C2 C11 H11B 109.5 . . ? C2 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C3 C12 H12A 109.5 . . ? C3 C12 H12B 109.5 . . ? C3 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C1 118.5(4) . . ? C20 C15 C1 122.1(3) . . ? C20 C15 C16 119.4(4) . . ? C15 C16 H16 120.1 . . ? C17 C16 C15 119.8(4) . . ? C17 C16 H16 120.1 . . ? C16 C17 O4 124.7(4) . . ? C18 C17 O4 114.2(4) . . ? C18 C17 C16 121.1(4) . . ? O5 C18 C19 120.1(5) . . ? C17 C18 O5 120.2(4) . . ? C17 C18 C19 119.6(4) . . ? O6 C19 C18 114.8(4) . . ? O6 C19 C20 125.7(4) . . ? C20 C19 C18 119.4(4) . . ? C15 C20 C19 120.6(4) . . ? C15 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? O4 C21 H21A 109.5 . . ? O4 C21 H21B 109.5 . . ? O4 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O6 C22 H22A 109.5 . . ? O6 C22 H22B 109.5 . . ? O6 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 O1 C6 C7 O2 6.5(7) . . . . ? O1 C6 C7 C8 -176.8(4) . . . . ? O2 C7 C8 O3 -0.9(7) . . . . ? O2 C7 C8 C9 179.7(4) . . . . ? O3 C8 C9 C10 179.8(4) . . . . ? O4 C17 C18 O5 -0.9(7) . . . . ? O4 C17 C18 C19 178.0(4) . . . . ? O5 C18 C19 O6 -0.7(7) . . . . ? O5 C18 C19 C20 -179.5(5) . . . . ? O6 C19 C20 C15 -179.2(5) . . . . ? C1 C2 C3 C4 0.2(6) . . . . ? C1 C2 C3 C12 -179.8(4) . . . . ? C1 C15 C16 C17 -177.9(4) . . . . ? C1 C15 C20 C19 178.3(4) . . . . ? C2 C1 C10 C5 1.1(6) . . . . ? C2 C1 C10 C9 -178.2(4) . . . . ? C2 C1 C15 C16 77.3(5) . . . . ? C2 C1 C15 C20 -101.9(5) . . . . ? C2 C3 C4 C5 1.4(7) . . . . ? C3 C4 C5 C6 178.3(4) . . . . ? C3 C4 C5 C10 -1.7(6) . . . . ? C4 C5 C6 O1 -4.2(7) . . . . ? C4 C5 C6 C7 -177.5(4) . . . . ? C4 C5 C10 C1 0.4(6) . . . . ? C4 C5 C10 C9 179.7(4) . . . . ? C5 C6 C7 O2 179.6(5) . . . . ? C5 C6 C7 C8 -3.8(7) . . . . ? C6 C5 C10 C1 -179.6(4) . . . . ? C6 C5 C10 C9 -0.3(6) . . . . ? C6 C7 C8 O3 -177.6(4) . . . . ? C6 C7 C8 C9 3.0(7) . . . . ? C7 C8 C9 C10 -0.8(7) . . . . ? C8 C9 C10 C1 178.8(4) . . . . ? C8 C9 C10 C5 -0.5(6) . . . . ? C10 C1 C2 C3 -1.4(6) . . . . ? C10 C1 C2 C11 -179.8(4) . . . . ? C10 C1 C15 C16 -101.0(4) . . . . ? C10 C1 C15 C20 79.8(5) . . . . ? C10 C5 C6 O1 175.7(4) . . . . ? C10 C5 C6 C7 2.5(7) . . . . ? C11 C2 C3 C4 178.6(4) . . . . ? C11 C2 C3 C12 -1.3(6) . . . . ? C12 C3 C4 C5 -178.7(4) . . . . ? C13 O1 C6 C5 111.2(7) . . . . ? C13 O1 C6 C7 -75.5(8) . . . . ? C14 O3 C8 C7 165.5(4) . . . . ? C14 O3 C8 C9 -15.1(7) . . . . ? C15 C1 C2 C3 -179.8(4) . . . . ? C15 C1 C2 C11 1.8(6) . . . . ? C15 C1 C10 C5 179.4(3) . . . . ? C15 C1 C10 C9 0.1(6) . . . . ? C15 C16 C17 O4 -179.4(4) . . . . ? C15 C16 C17 C18 -0.2(6) . . . . ? C16 C15 C20 C19 -0.9(6) . . . . ? C16 C17 C18 O5 179.8(4) . . . . ? C16 C17 C18 C19 -1.3(7) . . . . ? C17 C18 C19 O6 -179.6(4) . . . . ? C17 C18 C19 C20 1.7(8) . . . . ? C18 C19 C20 C15 -0.6(7) . . . . ? C20 C15 C16 C17 1.3(6) . . . . ? C21 O4 C17 C16 0.4(6) . . . . ? C21 O4 C17 C18 -178.9(4) . . . . ? C22 O6 C19 C18 178.4(5) . . . . ? C22 O6 C19 C20 -2.9(8) . . . . ? data_c2c _database_code_depnum_ccdc_archive 'CCDC 912718' #TrackingRef 'Sacidumlignan D.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 O7' _chemical_formula_weight 404.44 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 C2/c 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' '-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 12.701(9) _cell_length_b 13.483(10) _cell_length_c 24.743(18) _cell_angle_alpha 90.00 _cell_angle_beta 95.229(6) _cell_angle_gamma 90.00 _cell_volume 4220(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3758 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 22.59 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9731 _exptl_absorpt_correction_T_max 0.9795 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14943 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3936 _reflns_number_gt 2621 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3936 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1754 _refine_ls_wR_factor_gt 0.1482 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.11991(17) 0.82614(15) 0.67888(9) 0.0371(5) Uani 1 1 d . . . C2 C 0.07076(18) 0.73576(15) 0.66854(10) 0.0438(6) Uani 1 1 d . . . H2 H 0.0116 0.7322 0.6435 0.053 Uiso 1 1 calc R . . C3 C 0.10825(19) 0.65022(16) 0.69491(11) 0.0477(6) Uani 1 1 d . . . C4 C 0.19648(18) 0.65390(16) 0.73204(10) 0.0433(6) Uani 1 1 d . . . C5 C 0.24516(18) 0.74483(16) 0.74282(9) 0.0427(6) Uani 1 1 d . . . C6 C 0.20795(18) 0.83005(16) 0.71686(9) 0.0420(6) Uani 1 1 d . . . H6 H 0.2416 0.8903 0.7247 0.050 Uiso 1 1 calc R . . C7 C -0.0284(3) 0.5500(2) 0.65270(17) 0.0966(13) Uani 1 1 d . . . H7A H -0.0803 0.5947 0.6648 0.145 Uiso 1 1 calc R . . H7B H -0.0543 0.4832 0.6537 0.145 Uiso 1 1 calc R . . H7C H -0.0149 0.5666 0.6162 0.145 Uiso 1 1 calc R . . C8 C 0.3847(2) 0.8291(2) 0.79406(13) 0.0735(9) Uani 1 1 d . . . H8A H 0.4087 0.8580 0.7619 0.110 Uiso 1 1 calc R . . H8B H 0.4442 0.8161 0.8198 0.110 Uiso 1 1 calc R . . H8C H 0.3373 0.8741 0.8096 0.110 Uiso 1 1 calc R . . C9 C 0.17102(16) 0.95226(15) 0.61118(8) 0.0370(5) Uani 1 1 d . . . C10 C 0.18636(17) 1.05178(16) 0.60018(9) 0.0400(5) Uani 1 1 d . . . H10 H 0.1480 1.0995 0.6171 0.048 Uiso 1 1 calc R . . C11 C 0.25802(18) 1.08117(18) 0.56432(9) 0.0453(6) Uani 1 1 d . . . C12 C 0.31647(18) 1.0105(2) 0.53958(10) 0.0506(6) Uani 1 1 d . . . C13 C 0.30301(19) 0.9115(2) 0.55119(10) 0.0518(6) Uani 1 1 d . . . C14 C 0.23073(18) 0.88163(18) 0.58638(9) 0.0460(6) Uani 1 1 d . . . H14 H 0.2219 0.8146 0.5935 0.055 Uiso 1 1 calc R . . C15 C 0.2189(3) 1.2510(2) 0.57529(14) 0.0809(10) Uani 1 1 d . . . H15A H 0.1450 1.2375 0.5668 0.121 Uiso 1 1 calc R . . H15B H 0.2355 1.3148 0.5610 0.121 Uiso 1 1 calc R . . H15C H 0.2350 1.2510 0.6140 0.121 Uiso 1 1 calc R . . C16 C 0.3851(3) 0.7536(3) 0.54821(14) 0.0942(12) Uani 1 1 d . . . H16A H 0.3999 0.7594 0.5868 0.141 Uiso 1 1 calc R . . H16B H 0.4443 0.7236 0.5330 0.141 Uiso 1 1 calc R . . H16C H 0.3235 0.7130 0.5403 0.141 Uiso 1 1 calc R . . C17 C 0.08632(16) 0.92085(14) 0.64785(9) 0.0352(5) Uani 1 1 d . . . C18 C -0.02521(17) 0.91623(16) 0.61625(9) 0.0388(5) Uani 1 1 d . . . H18 H -0.0678 0.8698 0.6355 0.047 Uiso 1 1 calc R . . C19 C -0.06963(18) 1.01977(17) 0.62380(10) 0.0466(6) Uani 1 1 d . . . H19 H -0.0385 1.0655 0.5989 0.056 Uiso 1 1 calc R . . C20 C -0.02605(19) 1.04282(19) 0.68093(10) 0.0517(6) Uani 1 1 d . . . H20A H -0.0229 1.1139 0.6867 0.062 Uiso 1 1 calc R . . H20B H -0.0701 1.0137 0.7068 0.062 Uiso 1 1 calc R . . C21 C -0.0293(2) 0.8819(2) 0.55743(10) 0.0557(7) Uani 1 1 d . . . H21A H -0.1006 0.8864 0.5410 0.084 Uiso 1 1 calc R . . H21B H -0.0056 0.8144 0.5563 0.084 Uiso 1 1 calc R . . H21C H 0.0157 0.9233 0.5379 0.084 Uiso 1 1 calc R . . C22 C -0.18975(19) 1.0274(2) 0.61509(13) 0.0665(8) Uani 1 1 d . . . H22A H -0.2209 0.9804 0.6380 0.100 Uiso 1 1 calc R . . H22B H -0.2126 1.0134 0.5778 0.100 Uiso 1 1 calc R . . H22C H -0.2114 1.0932 0.6240 0.100 Uiso 1 1 calc R . . O1 O 0.06528(15) 0.55818(12) 0.68677(9) 0.0742(7) Uani 1 1 d . . . O2 O 0.23187(14) 0.56773(11) 0.75631(8) 0.0600(5) Uani 1 1 d . . . H2A H 0.2894 0.5774 0.7733 0.090 Uiso 1 1 calc R . . O3 O 0.33171(14) 0.73990(12) 0.78057(7) 0.0607(5) Uani 1 1 d . . . O4 O 0.07777(12) 1.00078(10) 0.68714(6) 0.0401(4) Uani 1 1 d . . . O5 O 0.27904(15) 1.17754(13) 0.55201(8) 0.0672(6) Uani 1 1 d . . . O6 O 0.38974(15) 1.04055(16) 0.50547(8) 0.0752(6) Uani 1 1 d . . . H6A H 0.4288 0.9940 0.4999 0.113 Uiso 1 1 calc R . . O7 O 0.36672(17) 0.84816(16) 0.52555(9) 0.0793(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 0.0372(12) 0.0337(12) 0.0400(13) 0.0021(9) 0.0025(10) 0.0008(9) C2 0.0373(12) 0.0385(13) 0.0534(14) 0.0045(11) -0.0070(11) -0.0010(10) C3 0.0446(14) 0.0315(12) 0.0651(16) 0.0044(11) -0.0051(12) -0.0037(10) C4 0.0447(14) 0.0307(12) 0.0535(14) 0.0066(10) -0.0008(11) 0.0030(9) C5 0.0437(13) 0.0368(12) 0.0454(14) 0.0017(10) -0.0077(11) 0.0020(10) C6 0.0471(14) 0.0305(11) 0.0468(13) 0.0013(10) -0.0043(11) -0.0042(9) C7 0.084(2) 0.0510(18) 0.143(3) 0.0097(19) -0.053(2) -0.0187(15) C8 0.0668(18) 0.0582(18) 0.089(2) 0.0040(15) -0.0297(16) -0.0144(14) C9 0.0358(12) 0.0370(12) 0.0373(12) 0.0032(9) -0.0008(9) -0.0004(9) C10 0.0407(12) 0.0396(13) 0.0397(12) 0.0029(10) 0.0038(10) 0.0026(10) C11 0.0417(13) 0.0479(14) 0.0455(14) 0.0111(11) 0.0000(11) -0.0034(11) C12 0.0404(13) 0.0696(17) 0.0424(14) 0.0110(12) 0.0077(11) 0.0021(12) C13 0.0479(14) 0.0616(17) 0.0466(14) 0.0001(12) 0.0084(12) 0.0139(12) C14 0.0485(14) 0.0415(13) 0.0482(14) 0.0009(11) 0.0056(12) 0.0054(10) C15 0.104(3) 0.0437(16) 0.099(2) 0.0105(15) 0.034(2) -0.0079(16) C16 0.110(3) 0.089(3) 0.086(2) -0.0057(19) 0.019(2) 0.054(2) C17 0.0380(12) 0.0309(11) 0.0364(12) -0.0018(9) 0.0012(9) 0.0003(9) C18 0.0368(12) 0.0390(12) 0.0398(12) 0.0035(10) -0.0005(10) -0.0007(9) C19 0.0432(13) 0.0454(14) 0.0506(15) 0.0058(11) 0.0015(11) 0.0056(11) C20 0.0470(14) 0.0540(15) 0.0538(16) -0.0081(12) 0.0024(12) 0.0116(11) C21 0.0525(15) 0.0656(17) 0.0475(15) -0.0069(12) -0.0041(12) 0.0002(13) C22 0.0466(15) 0.0700(18) 0.081(2) -0.0016(15) -0.0065(14) 0.0121(13) O1 0.0658(12) 0.0359(10) 0.1125(17) 0.0117(10) -0.0372(12) -0.0114(8) O2 0.0569(11) 0.0358(9) 0.0823(14) 0.0147(8) -0.0213(10) 0.0005(8) O3 0.0645(11) 0.0406(10) 0.0704(12) 0.0051(8) -0.0295(10) -0.0034(8) O4 0.0428(9) 0.0368(8) 0.0402(9) -0.0035(6) 0.0005(7) 0.0046(7) O5 0.0722(13) 0.0516(11) 0.0812(14) 0.0206(9) 0.0261(11) -0.0025(9) O6 0.0619(13) 0.0961(16) 0.0723(14) 0.0234(12) 0.0318(11) 0.0111(11) O7 0.0837(14) 0.0812(15) 0.0790(14) 0.0030(11) 0.0404(12) 0.0272(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.382(3) . ? C1 C6 1.395(3) . ? C1 C17 1.530(3) . ? C2 C3 1.388(3) . ? C2 H2 0.9300 . ? C3 O1 1.363(3) . ? C3 C4 1.384(3) . ? C4 O2 1.365(3) . ? C4 C5 1.388(3) . ? C5 O3 1.378(3) . ? C5 C6 1.379(3) . ? C6 H6 0.9300 . ? C7 O1 1.398(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 O3 1.403(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.386(3) . ? C9 C14 1.394(3) . ? C9 C17 1.529(3) . ? C10 C11 1.386(3) . ? C10 H10 0.9300 . ? C11 O5 1.366(3) . ? C11 C12 1.385(3) . ? C12 O6 1.373(3) . ? C12 C13 1.380(4) . ? C13 O7 1.371(3) . ? C13 C14 1.381(3) . ? C14 H14 0.9300 . ? C15 O5 1.407(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 O7 1.404(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O4 1.462(3) . ? C17 C18 1.556(3) . ? C18 C19 1.524(3) . ? C18 C21 1.524(3) . ? C18 H18 0.9800 . ? C19 C20 1.503(3) . ? C19 C22 1.525(4) . ? C19 H19 0.9800 . ? C20 O4 1.431(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? O2 H2A 0.8200 . ? O6 H6A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.60(19) . . ? C2 C1 C17 122.8(2) . . ? C6 C1 C17 118.44(18) . . ? C1 C2 C3 121.1(2) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? O1 C3 C4 114.82(19) . . ? O1 C3 C2 124.9(2) . . ? C4 C3 C2 120.3(2) . . ? O2 C4 C3 118.4(2) . . ? O2 C4 C5 123.0(2) . . ? C3 C4 C5 118.6(2) . . ? O3 C5 C6 125.1(2) . . ? O3 C5 C4 113.68(18) . . ? C6 C5 C4 121.3(2) . . ? C5 C6 C1 120.2(2) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 118.9(2) . . ? C10 C9 C17 120.24(19) . . ? C14 C9 C17 120.83(19) . . ? C11 C10 C9 121.0(2) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? O5 C11 C12 115.6(2) . . ? O5 C11 C10 124.6(2) . . ? C12 C11 C10 119.8(2) . . ? O6 C12 C13 121.2(2) . . ? O6 C12 C11 119.3(2) . . ? C13 C12 C11 119.5(2) . . ? O7 C13 C12 114.6(2) . . ? O7 C13 C14 124.4(2) . . ? C12 C13 C14 121.0(2) . . ? C13 C14 C9 119.9(2) . . ? C13 C14 H14 120.1 . . ? C9 C14 H14 120.1 . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O7 C16 H16A 109.5 . . ? O7 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O7 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 C17 C9 106.82(16) . . ? O4 C17 C1 108.40(17) . . ? C9 C17 C1 110.47(17) . . ? O4 C17 C18 104.14(16) . . ? C9 C17 C18 111.75(18) . . ? C1 C17 C18 114.72(17) . . ? C19 C18 C21 114.50(19) . . ? C19 C18 C17 103.42(17) . . ? C21 C18 C17 116.28(19) . . ? C19 C18 H18 107.4 . . ? C21 C18 H18 107.4 . . ? C17 C18 H18 107.4 . . ? C20 C19 C18 101.30(18) . . ? C20 C19 C22 113.4(2) . . ? C18 C19 C22 114.9(2) . . ? C20 C19 H19 109.0 . . ? C18 C19 H19 109.0 . . ? C22 C19 H19 109.0 . . ? O4 C20 C19 106.03(18) . . ? O4 C20 H20A 110.5 . . ? C19 C20 H20A 110.5 . . ? O4 C20 H20B 110.5 . . ? C19 C20 H20B 110.5 . . ? H20A C20 H20B 108.7 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C3 O1 C7 117.89(19) . . ? C4 O2 H2A 109.5 . . ? C5 O3 C8 117.10(18) . . ? C20 O4 C17 110.13(16) . . ? C11 O5 C15 117.0(2) . . ? C12 O6 H6A 109.5 . . ? C13 O7 C16 117.7(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 C6 C1 C2 C3 -0.5(4) . . . . ? C17 C1 C2 C3 175.4(2) . . . . ? C1 C2 C3 O1 -179.3(2) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? O1 C3 C4 O2 0.3(4) . . . . ? C2 C3 C4 O2 -178.8(2) . . . . ? O1 C3 C4 C5 -179.9(2) . . . . ? C2 C3 C4 C5 1.0(4) . . . . ? O2 C4 C5 O3 -0.6(4) . . . . ? C3 C4 C5 O3 179.6(2) . . . . ? O2 C4 C5 C6 179.0(2) . . . . ? C3 C4 C5 C6 -0.8(4) . . . . ? O3 C5 C6 C1 179.4(2) . . . . ? C4 C5 C6 C1 -0.1(4) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? C17 C1 C6 C5 -175.4(2) . . . . ? C14 C9 C10 C11 1.4(3) . . . . ? C17 C9 C10 C11 -175.8(2) . . . . ? C9 C10 C11 O5 -178.8(2) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? O5 C11 C12 O6 0.2(3) . . . . ? C10 C11 C12 O6 -177.9(2) . . . . ? O5 C11 C12 C13 177.7(2) . . . . ? C10 C11 C12 C13 -0.3(4) . . . . ? O6 C12 C13 O7 -0.9(4) . . . . ? C11 C12 C13 O7 -178.4(2) . . . . ? O6 C12 C13 C14 178.7(2) . . . . ? C11 C12 C13 C14 1.2(4) . . . . ? O7 C13 C14 C9 178.8(2) . . . . ? C12 C13 C14 C9 -0.7(4) . . . . ? C10 C9 C14 C13 -0.5(3) . . . . ? C17 C9 C14 C13 176.7(2) . . . . ? C10 C9 C17 O4 -31.1(2) . . . . ? C14 C9 C17 O4 151.79(19) . . . . ? C10 C9 C17 C1 -148.77(19) . . . . ? C14 C9 C17 C1 34.1(3) . . . . ? C10 C9 C17 C18 82.2(2) . . . . ? C14 C9 C17 C18 -94.9(2) . . . . ? C2 C1 C17 O4 132.8(2) . . . . ? C6 C1 C17 O4 -51.2(2) . . . . ? C2 C1 C17 C9 -110.5(2) . . . . ? C6 C1 C17 C9 65.5(3) . . . . ? C2 C1 C17 C18 16.9(3) . . . . ? C6 C1 C17 C18 -167.10(19) . . . . ? O4 C17 C18 C19 23.6(2) . . . . ? C9 C17 C18 C19 -91.4(2) . . . . ? C1 C17 C18 C19 141.90(19) . . . . ? O4 C17 C18 C21 149.98(18) . . . . ? C9 C17 C18 C21 35.0(3) . . . . ? C1 C17 C18 C21 -91.7(2) . . . . ? C21 C18 C19 C20 -164.0(2) . . . . ? C17 C18 C19 C20 -36.5(2) . . . . ? C21 C18 C19 C22 73.4(3) . . . . ? C17 C18 C19 C22 -159.1(2) . . . . ? C18 C19 C20 O4 37.1(2) . . . . ? C22 C19 C20 O4 160.8(2) . . . . ? C4 C3 O1 C7 175.6(3) . . . . ? C2 C3 O1 C7 -5.4(4) . . . . ? C6 C5 O3 C8 1.1(4) . . . . ? C4 C5 O3 C8 -179.4(2) . . . . ? C19 C20 O4 C17 -23.2(2) . . . . ? C9 C17 O4 C20 117.75(19) . . . . ? C1 C17 O4 C20 -123.20(19) . . . . ? C18 C17 O4 C20 -0.6(2) . . . . ? C12 C11 O5 C15 178.3(2) . . . . ? C10 C11 O5 C15 -3.8(4) . . . . ? C12 C13 O7 C16 158.6(3) . . . . ? C14 C13 O7 C16 -21.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.192 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.038