# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Young Keun Chung' _publ_contact_author_address ; School of Chemistry, Seoul National University, Seoul 151-747 N60, Korea ; _publ_contact_author_email ykchung@plaza.snu.ac.kr _publ_contact_author_phone 82-2-880-6662 _publ_contact_author_fax 82-2-889-0310 loop_ _publ_author_name _publ_author_address 'Young Keun Chung' ; School of Chemistry, Seoul National University, Seoul 151-747 N60, Korea ; 'Do Han Kim' ; School of Chemistry, Seoul National University, Seoul 151-747 N60, Korea ; _publ_section_title ; Tandem Pauson-Khand reaction and Diels-Alder reaction for access to polycycles in a one-pot reaction ; data_1a _database_code_depnum_ccdc_archive 'CCDC 247698' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 O5' _chemical_formula_weight 372.44 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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 17.0589(6) _cell_length_b 7.3377(3) _cell_length_c 17.2860(7) _cell_angle_alpha 90.00 _cell_angle_beta 118.849(2) _cell_angle_gamma 90.00 _cell_volume 1895.21(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour none _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7660 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4349 _reflns_number_gt 3097 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1235P)^2^+0.1237P] 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 4349 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.2004 _refine_ls_wR_factor_gt 0.1776 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.006 _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 0.53186(16) 1.3512(4) 0.33629(18) 0.0593(6) Uani 1 1 d . . . H1A H 0.4999 1.4240 0.2833 0.089 Uiso 1 1 calc R . . H1B H 0.5929 1.3951 0.3693 0.089 Uiso 1 1 calc R . . C2 C 0.48423(16) 1.3558(3) 0.39354(17) 0.0587(6) Uani 1 1 d . . . H2A H 0.5243 1.3992 0.4528 0.088 Uiso 1 1 calc R . . H2B H 0.4316 1.4332 0.3670 0.088 Uiso 1 1 calc R . . C3 C 0.45848(13) 1.1558(3) 0.39470(14) 0.0460(5) Uani 1 1 d . . . H3 H 0.4461 1.1244 0.4429 0.069 Uiso 1 1 calc R . . C4 C 0.38271(12) 1.1068(3) 0.30157(12) 0.0358(4) Uani 1 1 d . . . H4 H 0.3370 1.2025 0.2787 0.054 Uiso 1 1 calc R . . C5 C 0.33957(11) 0.9172(2) 0.29432(12) 0.0325(4) Uani 1 1 d . . . H5 H 0.3746 0.8555 0.3511 0.049 Uiso 1 1 calc R . . C6 C 0.24193(11) 0.9145(2) 0.27377(12) 0.0330(4) Uani 1 1 d . . . H6 H 0.2391 0.9660 0.3247 0.049 Uiso 1 1 calc R . . C7 C 0.20931(12) 0.7151(3) 0.26265(12) 0.0339(4) Uani 1 1 d . . . H7 H 0.1448 0.7210 0.2420 0.051 Uiso 1 1 calc R . . C8 C 0.22018(12) 0.6107(3) 0.19054(11) 0.0352(4) Uani 1 1 d . . . H8 H 0.2309 0.4826 0.2087 0.053 Uiso 1 1 calc R . . C9 C 0.13278(13) 0.6180(3) 0.10111(13) 0.0439(5) Uani 1 1 d . . . H9A H 0.0843 0.5666 0.1083 0.066 Uiso 1 1 calc R . . H9B H 0.1181 0.7442 0.0832 0.066 Uiso 1 1 calc R . . C10 C 0.14071(15) 0.5137(3) 0.02873(13) 0.0454(5) Uani 1 1 d . . . H10A H 0.1502 0.3853 0.0439 0.068 Uiso 1 1 calc R . . H10B H 0.0855 0.5257 -0.0266 0.068 Uiso 1 1 calc R . . C11 C 0.21776(15) 0.5867(3) 0.01806(13) 0.0454(5) Uani 1 1 d . . . H11A H 0.2057 0.7122 -0.0019 0.068 Uiso 1 1 calc R . . H11B H 0.2232 0.5162 -0.0266 0.068 Uiso 1 1 calc R . . C12 C 0.30569(15) 0.5772(3) 0.10487(14) 0.0460(5) Uani 1 1 d . . . H12A H 0.3216 0.4507 0.1210 0.069 Uiso 1 1 calc R . . H12B H 0.3529 0.6331 0.0970 0.069 Uiso 1 1 calc R . . C13 C 0.29843(12) 0.6734(3) 0.17839(12) 0.0340(4) Uani 1 1 d . . . C14 C 0.35161(11) 0.8105(3) 0.22586(12) 0.0337(4) Uani 1 1 d . . . C15 C 0.42293(12) 0.9019(3) 0.21375(12) 0.0384(5) Uani 1 1 d . . . C16 C 0.43315(12) 1.0963(3) 0.24706(13) 0.0381(5) Uani 1 1 d . . . H16 H 0.4078 1.1826 0.1977 0.057 Uiso 1 1 calc R . . C17 C 0.52956(13) 1.1491(3) 0.31383(14) 0.0466(5) Uani 1 1 d . . . H17 H 0.5746 1.1120 0.2971 0.070 Uiso 1 1 calc R . . C18 C 0.53909(14) 1.0573(4) 0.39781(14) 0.0518(6) Uani 1 1 d . . . H18A H 0.5312 0.9262 0.3919 0.078 Uiso 1 1 calc R . . H18B H 0.5950 1.0872 0.4500 0.078 Uiso 1 1 calc R . . C19 C 0.18062(12) 1.0257(3) 0.19326(13) 0.0357(4) Uani 1 1 d . . . C20 C 0.03182(15) 1.1351(4) 0.11348(19) 0.0692(8) Uani 1 1 d . . . H20A H 0.0343 1.2628 0.1265 0.104 Uiso 1 1 calc R . . H20B H -0.0257 1.0876 0.1004 0.104 Uiso 1 1 calc R . . H20C H 0.0410 1.1176 0.0634 0.104 Uiso 1 1 calc R . . C21 C 0.25087(13) 0.6256(3) 0.35325(12) 0.0381(5) Uani 1 1 d . . . C22 C 0.28092(16) 0.3518(3) 0.43376(14) 0.0525(6) Uani 1 1 d . . . H22A H 0.3422 0.3834 0.4729 0.079 Uiso 1 1 calc R . . H22B H 0.2761 0.2224 0.4243 0.079 Uiso 1 1 calc R . . H22C H 0.2445 0.3882 0.4595 0.079 Uiso 1 1 calc R . . O1 O 0.46801(10) 0.8357(2) 0.18329(11) 0.0581(5) Uani 1 1 d . . . O2 O 0.19915(9) 1.0917(2) 0.14091(10) 0.0535(4) Uani 1 1 d . . . O3 O 0.10030(9) 1.0411(2) 0.18838(11) 0.0527(4) Uani 1 1 d . . . O4 O 0.27825(15) 0.7070(2) 0.42179(10) 0.0732(6) Uani 1 1 d . . . O5 O 0.25059(10) 0.44461(18) 0.34995(9) 0.0446(4) 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 0.0522(13) 0.0658(16) 0.0640(15) -0.0106(12) 0.0313(12) -0.0195(11) C2 0.0555(13) 0.0631(15) 0.0625(15) -0.0195(12) 0.0325(12) -0.0205(12) C3 0.0422(11) 0.0596(13) 0.0370(11) -0.0074(9) 0.0199(9) -0.0105(10) C4 0.0323(9) 0.0403(10) 0.0363(10) 0.0001(8) 0.0177(8) -0.0003(8) C5 0.0320(9) 0.0370(10) 0.0294(9) 0.0013(7) 0.0157(7) 0.0030(7) C6 0.0354(9) 0.0347(10) 0.0349(10) -0.0025(8) 0.0219(8) -0.0004(7) C7 0.0358(9) 0.0374(10) 0.0315(9) -0.0003(7) 0.0186(8) -0.0018(7) C8 0.0432(10) 0.0342(10) 0.0294(9) 0.0004(7) 0.0184(8) 0.0009(8) C9 0.0413(10) 0.0516(12) 0.0362(10) -0.0048(9) 0.0168(9) -0.0033(9) C10 0.0543(12) 0.0434(11) 0.0311(10) -0.0040(8) 0.0147(9) -0.0023(9) C11 0.0614(13) 0.0431(11) 0.0344(10) -0.0006(9) 0.0253(10) 0.0024(10) C12 0.0532(12) 0.0493(12) 0.0405(11) -0.0062(9) 0.0267(10) 0.0055(10) C13 0.0378(9) 0.0368(10) 0.0293(9) 0.0033(8) 0.0176(7) 0.0099(8) C14 0.0313(9) 0.0411(10) 0.0295(9) 0.0036(8) 0.0153(7) 0.0084(7) C15 0.0301(9) 0.0551(12) 0.0308(9) 0.0016(8) 0.0153(8) 0.0050(8) C16 0.0329(9) 0.0484(11) 0.0344(10) 0.0043(8) 0.0173(8) -0.0009(8) C17 0.0328(9) 0.0646(14) 0.0439(11) -0.0018(10) 0.0198(9) -0.0045(9) C18 0.0364(11) 0.0720(16) 0.0381(11) 0.0022(10) 0.0109(9) -0.0023(10) C19 0.0348(9) 0.0326(9) 0.0421(10) -0.0045(8) 0.0206(8) -0.0008(7) C20 0.0437(13) 0.0828(19) 0.0773(18) 0.0215(15) 0.0261(13) 0.0226(12) C21 0.0443(10) 0.0421(11) 0.0334(10) -0.0003(8) 0.0231(9) -0.0051(8) C22 0.0675(14) 0.0501(13) 0.0413(12) 0.0127(10) 0.0274(11) 0.0023(11) O1 0.0493(8) 0.0793(12) 0.0616(10) -0.0116(9) 0.0393(8) 0.0017(8) O2 0.0454(8) 0.0669(10) 0.0554(10) 0.0249(8) 0.0300(8) 0.0127(7) O3 0.0374(7) 0.0636(10) 0.0657(10) 0.0149(8) 0.0317(7) 0.0133(7) O4 0.1260(16) 0.0538(10) 0.0365(9) -0.0056(7) 0.0367(10) -0.0109(10) O5 0.0604(9) 0.0403(8) 0.0347(8) 0.0053(6) 0.0242(7) 0.0004(6) _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 C17 1.529(4) . ? C1 C2 1.555(3) . ? C2 C3 1.535(3) . ? C3 C18 1.531(3) . ? C3 C4 1.544(3) . ? C4 C5 1.550(3) . ? C4 C16 1.555(3) . ? C5 C14 1.513(2) . ? C5 C6 1.526(2) . ? C6 C19 1.514(3) . ? C6 C7 1.544(3) . ? C7 C21 1.522(3) . ? C7 C8 1.549(2) . ? C8 C13 1.519(2) . ? C8 C9 1.546(3) . ? C9 C10 1.527(3) . ? C10 C11 1.511(3) . ? C11 C12 1.528(3) . ? C12 C13 1.510(3) . ? C13 C14 1.338(3) . ? C14 C15 1.490(3) . ? C15 O1 1.223(2) . ? C15 C16 1.517(3) . ? C16 C17 1.535(3) . ? C17 C18 1.536(3) . ? C19 O2 1.196(2) . ? C19 O3 1.336(2) . ? C20 O3 1.434(3) . ? C21 O4 1.202(2) . ? C21 O5 1.329(2) . ? C22 O5 1.452(2) . ? 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 C17 C1 C2 103.04(18) . . ? C3 C2 C1 103.19(19) . . ? C18 C3 C2 101.18(17) . . ? C18 C3 C4 102.26(16) . . ? C2 C3 C4 108.07(18) . . ? C3 C4 C5 114.79(16) . . ? C3 C4 C16 102.34(14) . . ? C5 C4 C16 106.67(15) . . ? C14 C5 C6 110.85(15) . . ? C14 C5 C4 106.80(14) . . ? C6 C5 C4 116.91(15) . . ? C19 C6 C5 113.54(15) . . ? C19 C6 C7 110.40(15) . . ? C5 C6 C7 109.18(14) . . ? C21 C7 C6 108.68(15) . . ? C21 C7 C8 115.94(16) . . ? C6 C7 C8 113.14(14) . . ? C13 C8 C9 109.82(15) . . ? C13 C8 C7 114.57(15) . . ? C9 C8 C7 110.82(15) . . ? C10 C9 C8 112.20(17) . . ? C11 C10 C9 110.41(17) . . ? C10 C11 C12 111.33(17) . . ? C13 C12 C11 111.42(17) . . ? C14 C13 C12 124.12(17) . . ? C14 C13 C8 121.59(16) . . ? C12 C13 C8 114.15(16) . . ? C13 C14 C15 127.60(16) . . ? C13 C14 C5 124.12(16) . . ? C15 C14 C5 107.78(16) . . ? O1 C15 C14 127.4(2) . . ? O1 C15 C16 123.77(18) . . ? C14 C15 C16 108.78(15) . . ? C15 C16 C17 114.08(16) . . ? C15 C16 C4 106.30(15) . . ? C17 C16 C4 103.74(15) . . ? C1 C17 C16 108.82(18) . . ? C1 C17 C18 101.96(19) . . ? C16 C17 C18 100.75(16) . . ? C3 C18 C17 94.37(17) . . ? O2 C19 O3 123.74(18) . . ? O2 C19 C6 126.61(16) . . ? O3 C19 C6 109.65(16) . . ? O4 C21 O5 122.03(18) . . ? O4 C21 C7 124.49(19) . . ? O5 C21 C7 113.41(16) . . ? C19 O3 C20 117.49(17) . . ? C21 O5 C22 115.71(16) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.328 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.124 data_1b _database_code_depnum_ccdc_archive 'CCDC 247699' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 O5' _chemical_formula_weight 372.44 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 P21/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 10.8847(4) _cell_length_b 9.8634(5) _cell_length_c 18.9142(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.398(2) _cell_angle_gamma 90.00 _cell_volume 1975.37(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour none _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7780 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4503 _reflns_number_gt 3320 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1020P)^2^+0.1206P] 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 4503 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1783 _refine_ls_wR_factor_gt 0.1475 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_restrained_S_all 1.148 _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 0.3294(2) 0.8146(2) 0.32058(11) 0.0602(5) Uani 1 1 d . . . H1A H 0.3789 0.7401 0.3460 0.090 Uiso 1 1 calc R . . H1B H 0.2497 0.8196 0.3351 0.090 Uiso 1 1 calc R . . C2 C 0.4028(2) 0.9505(2) 0.33530(10) 0.0589(5) Uani 1 1 d . . . H2A H 0.3578 1.0156 0.3584 0.088 Uiso 1 1 calc R . . H2B H 0.4865 0.9367 0.3660 0.088 Uiso 1 1 calc R . . C3 C 0.41002(16) 0.99853(18) 0.25886(9) 0.0463(4) Uani 1 1 d . . . H3 H 0.4233 1.0962 0.2548 0.069 Uiso 1 1 calc R . . C4 C 0.50554(14) 0.90899(17) 0.23216(8) 0.0367(4) Uani 1 1 d . . . H4 H 0.5855 0.9033 0.2688 0.055 Uiso 1 1 calc R . . C5 C 0.52835(14) 0.94965(16) 0.15702(8) 0.0334(3) Uani 1 1 d . . . H5 H 0.4599 1.0105 0.1334 0.050 Uiso 1 1 calc R . . C6 C 0.65424(14) 1.02102(17) 0.15845(8) 0.0357(4) Uani 1 1 d . . . H6 H 0.7231 0.9646 0.1859 0.054 Uiso 1 1 calc R . . C7 C 0.66739(14) 1.03105(17) 0.07937(8) 0.0369(4) Uani 1 1 d . . . H7 H 0.5900 1.0732 0.0510 0.055 Uiso 1 1 calc R . . C8 C 0.67755(15) 0.88877(18) 0.04696(8) 0.0392(4) Uani 1 1 d . . . H8 H 0.6579 0.8990 -0.0060 0.059 Uiso 1 1 calc R . . C9 C 0.81009(16) 0.8245(2) 0.06943(10) 0.0493(4) Uani 1 1 d . . . H9A H 0.8714 0.8848 0.0560 0.074 Uiso 1 1 calc R . . H9B H 0.8330 0.8129 0.1218 0.074 Uiso 1 1 calc R . . C10 C 0.8139(2) 0.6875(2) 0.03283(11) 0.0601(5) Uani 1 1 d . . . H10A H 0.7999 0.7005 -0.0193 0.090 Uiso 1 1 calc R . . H10B H 0.8969 0.6476 0.0500 0.090 Uiso 1 1 calc R . . C11 C 0.71486(19) 0.5911(2) 0.04850(11) 0.0589(5) Uani 1 1 d . . . H11A H 0.7356 0.5679 0.0997 0.088 Uiso 1 1 calc R . . H11B H 0.7153 0.5082 0.0209 0.088 Uiso 1 1 calc R . . C12 C 0.58289(18) 0.65428(19) 0.02851(10) 0.0514(5) Uani 1 1 d . . . H12A H 0.5565 0.6648 -0.0238 0.077 Uiso 1 1 calc R . . H12B H 0.5232 0.5947 0.0440 0.077 Uiso 1 1 calc R . . C13 C 0.58323(15) 0.79021(18) 0.06450(8) 0.0380(4) Uani 1 1 d . . . C14 C 0.51602(14) 0.81988(16) 0.11355(8) 0.0350(3) Uani 1 1 d . . . C15 C 0.43404(15) 0.72580(17) 0.14390(9) 0.0396(4) Uani 1 1 d . . . C16 C 0.43789(15) 0.76934(17) 0.22135(9) 0.0406(4) Uani 1 1 d . . . H16 H 0.4847 0.7030 0.2558 0.061 Uiso 1 1 calc R . . C17 C 0.30839(17) 0.79871(19) 0.23821(10) 0.0478(4) Uani 1 1 d . . . H17 H 0.2414 0.7348 0.2163 0.072 Uiso 1 1 calc R . . C18 C 0.28398(17) 0.9458(2) 0.21255(11) 0.0507(4) Uani 1 1 d . . . H18A H 0.2112 0.9854 0.2262 0.076 Uiso 1 1 calc R . . H18B H 0.2771 0.9565 0.1608 0.076 Uiso 1 1 calc R . . C19 C 0.65703(15) 1.15567(17) 0.19664(8) 0.0400(4) Uani 1 1 d . . . C20 C 0.5653(2) 1.3748(2) 0.18795(12) 0.0671(6) Uani 1 1 d . . . H20A H 0.5478 1.3616 0.2349 0.101 Uiso 1 1 calc R . . H20B H 0.4970 1.4237 0.1574 0.101 Uiso 1 1 calc R . . H20C H 0.6422 1.4255 0.1930 0.101 Uiso 1 1 calc R . . C21 C 0.77688(16) 1.1198(2) 0.07190(9) 0.0454(4) Uani 1 1 d . . . C22 C 0.8805(2) 1.2197(3) -0.01141(13) 0.0702(6) Uani 1 1 d . . . H22A H 0.8686 1.3122 0.0013 0.105 Uiso 1 1 calc R . . H22B H 0.8809 1.2144 -0.0620 0.105 Uiso 1 1 calc R . . H22C H 0.9596 1.1870 0.0172 0.105 Uiso 1 1 calc R . . O1 O 0.37306(12) 0.63024(14) 0.11391(7) 0.0555(4) Uani 1 1 d . . . O2 O 0.71575(13) 1.17959(15) 0.25724(7) 0.0591(4) Uani 1 1 d . . . O3 O 0.57895(12) 1.24467(12) 0.15562(6) 0.0509(3) Uani 1 1 d . . . O4 O 0.85353(16) 1.1672(2) 0.12104(8) 0.0873(6) Uani 1 1 d . . . O5 O 0.77916(12) 1.13773(15) 0.00262(7) 0.0570(4) 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 0.0656(12) 0.0624(13) 0.0625(12) 0.0026(10) 0.0353(10) -0.0033(10) C2 0.0686(13) 0.0627(13) 0.0541(10) -0.0091(9) 0.0319(9) -0.0018(10) C3 0.0501(10) 0.0393(9) 0.0553(10) -0.0039(8) 0.0242(8) 0.0010(8) C4 0.0370(8) 0.0365(8) 0.0381(7) -0.0001(6) 0.0115(6) 0.0010(6) C5 0.0320(7) 0.0313(8) 0.0369(7) -0.0003(6) 0.0080(6) 0.0005(6) C6 0.0329(7) 0.0380(9) 0.0355(7) 0.0005(6) 0.0066(6) -0.0014(6) C7 0.0328(7) 0.0413(9) 0.0361(7) 0.0026(6) 0.0073(6) -0.0022(6) C8 0.0406(8) 0.0461(10) 0.0314(7) -0.0014(7) 0.0097(6) -0.0005(7) C9 0.0406(9) 0.0556(11) 0.0549(10) 0.0015(8) 0.0180(8) 0.0040(8) C10 0.0611(12) 0.0606(13) 0.0669(12) -0.0013(10) 0.0316(10) 0.0117(10) C11 0.0712(13) 0.0467(11) 0.0654(11) -0.0087(9) 0.0290(10) 0.0066(10) C12 0.0585(11) 0.0500(11) 0.0483(9) -0.0171(8) 0.0173(8) -0.0063(9) C13 0.0381(8) 0.0414(9) 0.0330(7) -0.0036(6) 0.0052(6) -0.0005(6) C14 0.0340(7) 0.0341(8) 0.0357(7) -0.0013(6) 0.0057(6) -0.0002(6) C15 0.0393(8) 0.0304(8) 0.0500(9) 0.0002(7) 0.0123(7) 0.0021(6) C16 0.0433(9) 0.0342(8) 0.0467(9) 0.0049(7) 0.0156(7) 0.0011(7) C17 0.0453(9) 0.0460(10) 0.0573(10) -0.0011(8) 0.0227(8) -0.0056(8) C18 0.0408(9) 0.0500(11) 0.0660(11) 0.0034(9) 0.0217(8) 0.0065(8) C19 0.0403(8) 0.0397(9) 0.0400(8) -0.0004(7) 0.0092(7) -0.0072(7) C20 0.0857(15) 0.0377(10) 0.0709(13) -0.0089(9) 0.0037(11) 0.0028(10) C21 0.0402(9) 0.0529(11) 0.0440(9) 0.0006(8) 0.0118(7) -0.0071(8) C22 0.0583(12) 0.0841(17) 0.0745(13) 0.0144(12) 0.0285(10) -0.0194(11) O1 0.0600(8) 0.0409(7) 0.0688(8) -0.0120(6) 0.0213(6) -0.0149(6) O2 0.0704(9) 0.0562(8) 0.0426(7) -0.0092(6) -0.0031(6) -0.0025(7) O3 0.0627(8) 0.0350(7) 0.0486(7) -0.0036(5) -0.0002(6) 0.0013(6) O4 0.0722(10) 0.1328(17) 0.0578(8) -0.0164(9) 0.0170(7) -0.0598(10) O5 0.0499(7) 0.0744(10) 0.0485(7) 0.0115(6) 0.0151(5) -0.0172(6) _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 C17 1.529(3) . ? C1 C2 1.552(3) . ? C2 C3 1.541(2) . ? C3 C4 1.536(2) . ? C3 C18 1.537(3) . ? C4 C5 1.551(2) . ? C4 C16 1.553(2) . ? C5 C14 1.510(2) . ? C5 C6 1.535(2) . ? C6 C19 1.509(2) . ? C6 C7 1.538(2) . ? C7 C21 1.512(2) . ? C7 C8 1.546(2) . ? C8 C13 1.506(2) . ? C8 C9 1.543(2) . ? C9 C10 1.523(3) . ? C10 C11 1.517(3) . ? C11 C12 1.531(3) . ? C12 C13 1.503(2) . ? C13 C14 1.340(2) . ? C14 C15 1.491(2) . ? C15 O1 1.215(2) . ? C15 C16 1.518(2) . ? C16 C17 1.543(2) . ? C17 C18 1.534(3) . ? C19 O2 1.1992(19) . ? C19 O3 1.338(2) . ? C20 O3 1.444(2) . ? C21 O4 1.191(2) . ? C21 O5 1.328(2) . ? C22 O5 1.441(2) . ? 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 C17 C1 C2 102.75(15) . . ? C3 C2 C1 103.48(15) . . ? C4 C3 C18 101.59(13) . . ? C4 C3 C2 108.51(15) . . ? C18 C3 C2 101.41(15) . . ? C3 C4 C5 114.64(13) . . ? C3 C4 C16 102.52(13) . . ? C5 C4 C16 106.28(12) . . ? C14 C5 C6 111.38(12) . . ? C14 C5 C4 105.47(12) . . ? C6 C5 C4 115.73(12) . . ? C19 C6 C5 109.32(12) . . ? C19 C6 C7 114.38(13) . . ? C5 C6 C7 107.23(11) . . ? C21 C7 C6 112.40(12) . . ? C21 C7 C8 111.01(13) . . ? C6 C7 C8 111.01(13) . . ? C13 C8 C9 108.41(14) . . ? C13 C8 C7 112.57(13) . . ? C9 C8 C7 114.34(13) . . ? C10 C9 C8 111.21(15) . . ? C11 C10 C9 111.81(15) . . ? C10 C11 C12 111.44(17) . . ? C13 C12 C11 110.33(15) . . ? C14 C13 C12 124.31(16) . . ? C14 C13 C8 121.39(15) . . ? C12 C13 C8 113.98(14) . . ? C13 C14 C15 127.00(15) . . ? C13 C14 C5 124.61(14) . . ? C15 C14 C5 107.66(12) . . ? O1 C15 C14 127.86(15) . . ? O1 C15 C16 124.06(15) . . ? C14 C15 C16 108.08(13) . . ? C15 C16 C17 115.49(14) . . ? C15 C16 C4 106.51(13) . . ? C17 C16 C4 103.55(13) . . ? C1 C17 C18 101.50(16) . . ? C1 C17 C16 107.55(16) . . ? C18 C17 C16 102.23(14) . . ? C17 C18 C3 94.21(14) . . ? O2 C19 O3 123.47(16) . . ? O2 C19 C6 125.30(15) . . ? O3 C19 C6 111.12(13) . . ? O4 C21 O5 123.23(16) . . ? O4 C21 C7 125.38(15) . . ? O5 C21 C7 111.38(13) . . ? C19 O3 C20 116.83(14) . . ? C21 O5 C22 116.50(15) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.763 _refine_diff_density_min -0.734 _refine_diff_density_rms 0.258 data_7c _database_code_depnum_ccdc_archive 'CCDC 257082' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 Cl2 O3' _chemical_formula_weight 507.42 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4991(6) _cell_length_b 15.8252(13) _cell_length_c 16.8571(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.267(5) _cell_angle_gamma 90.00 _cell_volume 2507.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour none _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.290 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9746 _diffrn_reflns_av_R_equivalents 0.0789 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 22.50 _reflns_number_total 3258 _reflns_number_gt 1847 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0965P)^2^+2.0252P] 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 SHELXL _refine_ls_extinction_coef 0.0025(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3258 _refine_ls_number_parameters 336 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1377 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.2124 _refine_ls_wR_factor_gt 0.1769 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.033 _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 0.2383(6) 0.7880(4) 0.1650(3) 0.0769(17) Uani 1 1 d . . . C2 C 0.3155(5) 0.7246(3) 0.2233(3) 0.0645(14) Uani 1 1 d . . . H2 H 0.2549 0.7044 0.2618 0.097 Uiso 1 1 calc R . . C3 C 0.4597(6) 0.7570(4) 0.2658(4) 0.0817(18) Uani 1 1 d . . . H3 H 0.4589 0.8150 0.2861 0.123 Uiso 1 1 calc R . . C4 C 0.5161(6) 0.6914(5) 0.3271(4) 0.0881(19) Uani 1 1 d . . . C5 C 0.5240(7) 0.6848(7) 0.4091(4) 0.119(3) Uani 1 1 d . . . H5 H 0.4959 0.7292 0.4393 0.143 Uiso 1 1 calc R . . C6 C 0.5745(10) 0.6108(9) 0.4450(5) 0.154(4) Uani 1 1 d . . . H6 H 0.5829 0.6057 0.5004 0.184 Uiso 1 1 calc R . . C7 C 0.6131(10) 0.5437(8) 0.4004(6) 0.145(3) Uani 1 1 d . . . H7 H 0.6440 0.4936 0.4260 0.174 Uiso 1 1 calc R . . C8 C 0.6062(7) 0.5500(5) 0.3162(4) 0.106(2) Uani 1 1 d . . . H8 H 0.6329 0.5054 0.2857 0.127 Uiso 1 1 calc R . . C9 C 0.5583(6) 0.6251(5) 0.2818(3) 0.0780(17) Uani 1 1 d . . . C10 C 0.5240(5) 0.6532(4) 0.1962(3) 0.0692(15) Uani 1 1 d . . . H10 H 0.5787 0.6248 0.1589 0.104 Uiso 1 1 calc R . . C11 C 0.3626(5) 0.6509(3) 0.1717(3) 0.0552(13) Uani 1 1 d . . . H11 H 0.3222 0.5968 0.1854 0.083 Uiso 1 1 calc R . . C12 C 0.3130(5) 0.6751(3) 0.0824(3) 0.0533(13) Uani 1 1 d . . . H12 H 0.3981 0.6884 0.0581 0.080 Uiso 1 1 calc R . . C13 C 0.2331(5) 0.6050(3) 0.0328(3) 0.0488(12) Uani 1 1 d . . . H13 H 0.1701 0.5748 0.0643 0.073 Uiso 1 1 calc R . . C14 C 0.3395(5) 0.5436(3) 0.0024(3) 0.0543(13) Uani 1 1 d . . . H14 H 0.4229 0.5305 0.0418 0.081 Uiso 1 1 calc R . . C15 C 0.2627(5) 0.4666(3) -0.0358(3) 0.0517(12) Uani 1 1 d . . . C16 C 0.2553(6) 0.3830(4) -0.0151(3) 0.0667(15) Uani 1 1 d . . . H16 H 0.3039 0.3626 0.0329 0.080 Uiso 1 1 calc R . . C17 C 0.1720(7) 0.3298(4) -0.0689(4) 0.0782(17) Uani 1 1 d . . . H17 H 0.1660 0.2728 -0.0565 0.094 Uiso 1 1 calc R . . C18 C 0.0997(6) 0.3591(4) -0.1387(4) 0.0782(17) Uani 1 1 d . . . H18 H 0.0450 0.3220 -0.1732 0.094 Uiso 1 1 calc R . . C19 C 0.1063(5) 0.4432(4) -0.1593(3) 0.0666(15) Uani 1 1 d . . . H19 H 0.0558 0.4633 -0.2070 0.080 Uiso 1 1 calc R . . C20 C 0.1890(5) 0.4969(3) -0.1079(3) 0.0545(13) Uani 1 1 d . . . C21 C 0.2267(5) 0.5894(3) -0.1089(3) 0.0576(13) Uani 1 1 d . . . H21 H 0.2154 0.6149 -0.1624 0.086 Uiso 1 1 calc R . . C22 C 0.1488(5) 0.6372(3) -0.0476(3) 0.0518(12) Uani 1 1 d . . . H22 H 0.0504 0.6170 -0.0523 0.078 Uiso 1 1 calc R . . C23 C 0.1484(5) 0.7336(3) -0.0604(3) 0.0576(13) Uani 1 1 d . . . H23 H 0.2362 0.7476 -0.0818 0.086 Uiso 1 1 calc R . . C24 C 0.0244(7) 0.7580(4) -0.1248(3) 0.0824(18) Uani 1 1 d . . . H24A H 0.0414 0.7338 -0.1755 0.124 Uiso 1 1 calc R . . H24B H -0.0618 0.7327 -0.1111 0.124 Uiso 1 1 calc R . . C25 C 0.0002(10) 0.8493(5) -0.1362(4) 0.125(3) Uani 1 1 d . . . H25A H -0.0839 0.8589 -0.1751 0.187 Uiso 1 1 calc R . . H25B H 0.0809 0.8750 -0.1562 0.187 Uiso 1 1 calc R . . C26 C -0.0194(15) 0.8886(6) -0.0560(5) 0.216(7) Uani 1 1 d . . . H26A H -0.0182 0.9495 -0.0622 0.323 Uiso 1 1 calc R . . H26B H -0.1135 0.8733 -0.0448 0.323 Uiso 1 1 calc R . . C27 C 0.0753(9) 0.8684(4) 0.0093(4) 0.107(2) Uani 1 1 d . . . H27A H 0.0261 0.8738 0.0557 0.161 Uiso 1 1 calc R . . H27B H 0.1488 0.9114 0.0145 0.161 Uiso 1 1 calc R . . C28 C 0.1495(6) 0.7839(3) 0.0159(3) 0.0610(14) Uani 1 1 d . . . C29 C 0.2263(5) 0.7551(3) 0.0828(3) 0.0600(14) Uani 1 1 d . . . O1 O 0.1944(7) 0.8553(3) 0.1873(3) 0.138(2) Uani 1 1 d . . . O2 O 0.5492(4) 0.7436(3) 0.2045(2) 0.0859(13) Uani 1 1 d . . . O3 O 0.3719(3) 0.5880(2) -0.06814(18) 0.0588(9) Uani 1 1 d . . . Cl1 Cl 0.2443(3) 0.41652(14) 0.19527(12) 0.1388(9) Uani 1 1 d D . . C01A C 0.203(2) 0.3807(9) 0.2861(9) 0.118(6) Uani 0.594(9) 1 d PD A 1 H01A H 0.2665 0.3345 0.3053 0.177 Uiso 0.594(9) 1 calc PR A 1 H01B H 0.1066 0.3597 0.2792 0.177 Uiso 0.594(9) 1 calc PR A 1 Cl2A Cl 0.2216(7) 0.4621(5) 0.3561(3) 0.185(3) Uani 0.594(9) 1 d PD A 1 C01B C 0.282(2) 0.417(2) 0.3021(10) 0.128(10) Uani 0.406(9) 1 d PD A 2 H01C H 0.3196 0.4708 0.3228 0.193 Uiso 0.406(9) 1 calc PR A 2 H01D H 0.3463 0.3719 0.3223 0.193 Uiso 0.406(9) 1 calc PR A 2 Cl2B Cl 0.1028(10) 0.3988(5) 0.3247(5) 0.160(5) Uani 0.406(9) 1 d PD A 2 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 0.102(4) 0.058(4) 0.065(4) -0.018(3) -0.006(3) 0.015(3) C2 0.065(3) 0.075(4) 0.051(3) -0.014(3) 0.000(3) 0.008(3) C3 0.079(4) 0.092(5) 0.072(4) -0.026(4) 0.001(3) -0.005(3) C4 0.072(4) 0.129(6) 0.058(4) -0.022(4) -0.009(3) 0.008(4) C5 0.076(4) 0.211(10) 0.064(5) -0.024(5) -0.015(4) 0.026(5) C6 0.115(7) 0.268(14) 0.071(6) 0.025(8) -0.011(5) 0.042(8) C7 0.130(7) 0.194(11) 0.098(7) 0.031(7) -0.028(6) 0.029(7) C8 0.086(5) 0.135(7) 0.086(6) 0.003(5) -0.022(4) 0.025(4) C9 0.062(3) 0.110(5) 0.056(4) -0.003(4) -0.012(3) 0.009(3) C10 0.068(4) 0.077(4) 0.063(4) -0.014(3) 0.008(3) -0.003(3) C11 0.055(3) 0.064(3) 0.045(3) -0.005(3) 0.002(2) 0.000(2) C12 0.060(3) 0.056(3) 0.043(3) -0.001(2) 0.003(2) 0.001(3) C13 0.057(3) 0.049(3) 0.040(3) -0.004(2) 0.004(2) 0.004(2) C14 0.056(3) 0.063(3) 0.042(3) 0.000(3) 0.002(2) 0.007(3) C15 0.062(3) 0.051(3) 0.043(3) -0.007(3) 0.012(2) 0.006(3) C16 0.087(4) 0.059(4) 0.058(3) 0.003(3) 0.022(3) 0.013(3) C17 0.096(4) 0.056(4) 0.088(5) -0.011(4) 0.032(4) -0.010(3) C18 0.081(4) 0.069(5) 0.085(5) -0.021(4) 0.012(4) -0.011(3) C19 0.065(3) 0.075(5) 0.058(3) -0.019(3) 0.001(3) 0.006(3) C20 0.064(3) 0.054(3) 0.046(3) -0.008(3) 0.010(3) 0.004(3) C21 0.069(3) 0.065(4) 0.038(3) 0.001(2) 0.006(2) 0.006(3) C22 0.058(3) 0.055(3) 0.042(3) 0.000(2) 0.005(2) 0.002(2) C23 0.070(3) 0.051(3) 0.051(3) 0.005(3) 0.004(3) 0.007(3) C24 0.112(5) 0.071(4) 0.058(4) 0.004(3) -0.008(3) 0.024(3) C25 0.189(8) 0.096(6) 0.081(5) 0.003(4) -0.008(5) 0.060(5) C26 0.420(19) 0.126(8) 0.083(6) -0.014(5) -0.022(8) 0.167(10) C27 0.165(7) 0.061(4) 0.086(5) -0.011(4) -0.017(5) 0.041(4) C28 0.083(4) 0.042(3) 0.056(3) -0.001(3) 0.006(3) 0.003(3) C29 0.077(3) 0.047(3) 0.053(3) -0.005(3) 0.000(3) -0.003(3) O1 0.224(6) 0.091(4) 0.082(3) -0.034(3) -0.030(3) 0.066(4) O2 0.076(3) 0.092(3) 0.091(3) -0.020(2) 0.015(2) -0.024(2) O3 0.058(2) 0.067(2) 0.054(2) -0.0030(17) 0.0151(16) -0.0008(17) Cl1 0.206(2) 0.1154(17) 0.0963(15) 0.0145(12) 0.0264(14) 0.0115(15) C01A 0.142(16) 0.077(12) 0.144(14) 0.004(9) 0.055(13) 0.015(10) Cl2A 0.217(6) 0.225(6) 0.109(3) -0.051(4) 0.012(3) 0.008(5) C01B 0.16(3) 0.11(2) 0.13(2) -0.003(16) 0.057(17) 0.053(18) Cl2B 0.198(8) 0.147(7) 0.147(6) 0.019(5) 0.061(6) 0.046(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.222(6) . ? C1 C29 1.469(7) . ? C1 C2 1.518(7) . ? C2 C3 1.540(7) . ? C2 C11 1.559(6) . ? C3 O2 1.444(7) . ? C3 C4 1.508(9) . ? C4 C5 1.377(9) . ? C4 C9 1.391(8) . ? C5 C6 1.373(12) . ? C6 C7 1.381(12) . ? C7 C8 1.414(11) . ? C8 C9 1.371(9) . ? C9 C10 1.500(8) . ? C10 O2 1.454(6) . ? C10 C11 1.530(7) . ? C11 C12 1.558(6) . ? C12 C29 1.512(7) . ? C12 C13 1.524(6) . ? C13 C14 1.542(6) . ? C13 C22 1.558(6) . ? C14 O3 1.452(5) . ? C14 C15 1.515(6) . ? C15 C16 1.372(7) . ? C15 C20 1.398(6) . ? C16 C17 1.397(8) . ? C17 C18 1.356(8) . ? C18 C19 1.380(8) . ? C19 C20 1.376(7) . ? C20 C21 1.508(7) . ? C21 O3 1.449(5) . ? C21 C22 1.551(6) . ? C22 C23 1.540(6) . ? C23 C28 1.511(7) . ? C23 C24 1.532(7) . ? C24 C25 1.471(8) . ? C25 C26 1.524(10) . ? C26 C27 1.356(10) . ? C27 C28 1.508(7) . ? C28 C29 1.333(7) . ? Cl1 C01A 1.728(13) . ? Cl1 C01B 1.785(17) . ? C01A Cl2A 1.738(13) . ? C01B Cl2B 1.816(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C29 127.9(5) . . ? O1 C1 C2 122.1(5) . . ? C29 C1 C2 110.0(5) . . ? C1 C2 C3 113.3(5) . . ? C1 C2 C11 106.5(4) . . ? C3 C2 C11 101.6(4) . . ? O2 C3 C4 101.6(5) . . ? O2 C3 C2 101.2(4) . . ? C4 C3 C2 107.1(5) . . ? C5 C4 C9 121.0(7) . . ? C5 C4 C3 134.7(7) . . ? C9 C4 C3 104.2(5) . . ? C6 C5 C4 118.2(8) . . ? C5 C6 C7 121.3(8) . . ? C6 C7 C8 120.9(9) . . ? C9 C8 C7 116.8(8) . . ? C8 C9 C4 121.8(6) . . ? C8 C9 C10 132.6(6) . . ? C4 C9 C10 105.3(6) . . ? O2 C10 C9 100.9(4) . . ? O2 C10 C11 101.1(4) . . ? C9 C10 C11 108.9(4) . . ? C10 C11 C12 114.0(4) . . ? C10 C11 C2 100.9(4) . . ? C12 C11 C2 106.6(4) . . ? C29 C12 C13 112.6(4) . . ? C29 C12 C11 106.8(4) . . ? C13 C12 C11 114.1(4) . . ? C12 C13 C14 110.0(4) . . ? C12 C13 C22 113.1(4) . . ? C14 C13 C22 101.3(3) . . ? O3 C14 C15 100.8(3) . . ? O3 C14 C13 101.2(3) . . ? C15 C14 C13 110.5(4) . . ? C16 C15 C20 120.9(5) . . ? C16 C15 C14 135.0(5) . . ? C20 C15 C14 104.1(4) . . ? C15 C16 C17 117.5(5) . . ? C18 C17 C16 121.8(6) . . ? C17 C18 C19 120.8(6) . . ? C20 C19 C18 118.7(5) . . ? C19 C20 C15 120.3(5) . . ? C19 C20 C21 135.0(5) . . ? C15 C20 C21 104.6(4) . . ? O3 C21 C20 101.0(4) . . ? O3 C21 C22 101.8(3) . . ? C20 C21 C22 109.2(4) . . ? C23 C22 C21 112.4(4) . . ? C23 C22 C13 115.9(4) . . ? C21 C22 C13 100.6(4) . . ? C28 C23 C24 112.4(4) . . ? C28 C23 C22 113.7(4) . . ? C24 C23 C22 109.6(4) . . ? C25 C24 C23 115.5(5) . . ? C24 C25 C26 108.8(6) . . ? C27 C26 C25 118.2(8) . . ? C26 C27 C28 121.1(6) . . ? C29 C28 C27 123.9(5) . . ? C29 C28 C23 118.5(4) . . ? C27 C28 C23 117.3(5) . . ? C28 C29 C1 129.5(5) . . ? C28 C29 C12 121.0(4) . . ? C1 C29 C12 109.4(4) . . ? C3 O2 C10 96.2(4) . . ? C21 O3 C14 95.5(3) . . ? C01A Cl1 C01B 31.2(7) . . ? Cl1 C01A Cl2A 110.2(8) . . ? Cl1 C01B Cl2B 98.9(10) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.389 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.056 data_7a _database_code_depnum_ccdc_archive 'CCDC 257083' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H25 O6' _chemical_formula_weight 421.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 8.6130(6) _cell_length_b 23.0367(9) _cell_length_c 10.7028(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.494(2) _cell_angle_gamma 90.00 _cell_volume 2113.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour none _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4392 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4383 _reflns_number_gt 3667 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0506P)^2^+0.6783P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(10) _refine_ls_number_reflns 4383 _refine_ls_number_parameters 284 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.238 _refine_ls_shift/su_mean 0.002 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 0.1098(3) 0.23099(10) 0.6463(2) 0.0389(5) Uani 1 1 d . . . C2 C 0.0449(3) 0.28813(9) 0.6921(2) 0.0345(5) Uani 1 1 d . . . H2 H -0.0424 0.3025 0.6350 0.052 Uiso 1 1 calc R . . C3 C 0.1725(3) 0.33451(11) 0.7194(2) 0.0449(6) Uani 1 1 d . . . H3 H 0.2417 0.3397 0.6527 0.067 Uiso 1 1 calc R . . C4 C 0.0954(3) 0.38932(10) 0.7597(2) 0.0419(6) Uani 1 1 d . . . C5 C 0.0503(4) 0.44051(11) 0.7007(3) 0.0562(7) Uani 1 1 d . . . H5 H 0.0705 0.4476 0.6182 0.067 Uiso 1 1 calc R . . C6 C -0.0263(4) 0.48120(12) 0.7684(3) 0.0649(9) Uani 1 1 d . . . H6 H -0.0552 0.5165 0.7311 0.078 Uiso 1 1 calc R . . C7 C -0.0605(3) 0.47051(12) 0.8890(3) 0.0569(7) Uani 1 1 d . . . H7 H -0.1110 0.4987 0.9323 0.068 Uiso 1 1 calc R . . C8 C -0.0205(3) 0.41802(11) 0.9470(2) 0.0476(6) Uani 1 1 d . . . H8 H -0.0462 0.4101 1.0277 0.057 Uiso 1 1 calc R . . C9 C 0.0589(3) 0.37780(10) 0.8811(2) 0.0390(5) Uani 1 1 d . . . C10 C 0.1118(3) 0.31605(10) 0.9063(2) 0.0391(5) Uani 1 1 d . . . H10 H 0.1298 0.3055 0.9952 0.059 Uiso 1 1 calc R . . C11 C -0.0041(2) 0.27624(9) 0.82626(19) 0.0308(4) Uani 1 1 d . . . H11 H -0.1128 0.2873 0.8335 0.046 Uiso 1 1 calc R . . C12 C 0.0232(2) 0.21077(9) 0.85114(18) 0.0284(4) Uani 1 1 d . . . H12 H 0.1134 0.2074 0.9138 0.043 Uiso 1 1 calc R . . C13 C -0.1106(2) 0.17728(8) 0.90151(19) 0.0289(4) Uani 1 1 d . . . H13 H -0.1236 0.1924 0.9855 0.043 Uiso 1 1 calc R . . C14 C -0.0608(2) 0.11309(9) 0.91625(19) 0.0310(4) Uani 1 1 d . . . H14 H -0.1497 0.0913 0.9427 0.046 Uiso 1 1 calc R . . C15 C -0.0160(3) 0.08565(9) 0.7933(2) 0.0347(5) Uani 1 1 d . . . H15 H 0.0619 0.0556 0.8167 0.052 Uiso 1 1 calc R . . C16 C -0.1565(3) 0.05521(11) 0.7204(2) 0.0493(6) Uani 1 1 d . . . H16A H -0.1997 0.0269 0.7746 0.074 Uiso 1 1 calc R . . H16B H -0.2368 0.0837 0.6966 0.074 Uiso 1 1 calc R . . C17 C -0.1104(4) 0.02473(12) 0.6026(3) 0.0578(7) Uani 1 1 d . . . H17A H -0.0382 -0.0065 0.6268 0.087 Uiso 1 1 calc R . . H17B H -0.2025 0.0079 0.5572 0.087 Uiso 1 1 calc R . . C18 C -0.0353(4) 0.06646(12) 0.5183(3) 0.0523(7) Uani 1 1 d . . . H18A H -0.1125 0.0944 0.4845 0.078 Uiso 1 1 calc R . . H18B H 0.0010 0.0452 0.4485 0.078 Uiso 1 1 calc R . . C19 C 0.1017(3) 0.09876(11) 0.5876(2) 0.0442(6) Uani 1 1 d . . . H19A H 0.1864 0.0717 0.6088 0.066 Uiso 1 1 calc R . . H19B H 0.1386 0.1282 0.5328 0.066 Uiso 1 1 calc R . . C20 C 0.0562(3) 0.12708(9) 0.7058(2) 0.0334(5) Uani 1 1 d . . . C21 C 0.0689(2) 0.18383(9) 0.73166(18) 0.0318(5) Uani 1 1 d . . . C22 C -0.2654(3) 0.18409(9) 0.8229(2) 0.0330(5) Uani 1 1 d . . . C23 C -0.5350(3) 0.16517(14) 0.8197(3) 0.0659(8) Uani 1 1 d . . . H23A H -0.5646 0.2051 0.8280 0.099 Uiso 1 1 calc R . . H23B H -0.6053 0.1408 0.8604 0.099 Uiso 1 1 calc R . . H23C H -0.5396 0.1552 0.7323 0.099 Uiso 1 1 calc R . . C24 C 0.0713(3) 0.10845(10) 1.0204(2) 0.0370(5) Uani 1 1 d . . . C25 C 0.1375(4) 0.13048(15) 1.2356(3) 0.0643(8) Uani 1 1 d . . . H25A H 0.1572 0.0919 1.2669 0.096 Uiso 1 1 calc R . . H25B H 0.0977 0.1538 1.2996 0.096 Uiso 1 1 calc R . . H25C H 0.2328 0.1471 1.2123 0.096 Uiso 1 1 calc R . . O1 O 0.1830(3) 0.22745(9) 0.55517(19) 0.0656(6) Uani 1 1 d . . . O2 O 0.24825(19) 0.31328(7) 0.83728(17) 0.0475(4) Uani 1 1 d . . . O3 O -0.2879(2) 0.21099(8) 0.72643(15) 0.0489(4) Uani 1 1 d . . . O4 O -0.37783(18) 0.15681(8) 0.87731(16) 0.0457(4) Uani 1 1 d . . . O5 O 0.1983(2) 0.09027(11) 1.01045(19) 0.0690(6) Uani 1 1 d . . . O6 O 0.0247(2) 0.12837(8) 1.12751(15) 0.0460(4) 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 0.0442(13) 0.0396(13) 0.0344(12) -0.0016(10) 0.0122(10) -0.0074(10) C2 0.0403(12) 0.0346(11) 0.0292(10) 0.0032(9) 0.0060(9) -0.0049(9) C3 0.0465(14) 0.0459(14) 0.0447(14) -0.0019(11) 0.0166(11) -0.0125(11) C4 0.0404(13) 0.0351(13) 0.0508(14) -0.0017(10) 0.0073(11) -0.0121(10) C5 0.0693(19) 0.0401(14) 0.0592(17) 0.0080(13) 0.0059(14) -0.0158(14) C6 0.069(2) 0.0373(15) 0.086(2) 0.0056(14) -0.0054(18) -0.0080(14) C7 0.0509(16) 0.0417(15) 0.077(2) -0.0138(14) 0.0026(15) -0.0009(12) C8 0.0504(15) 0.0416(14) 0.0511(15) -0.0073(11) 0.0061(12) -0.0066(11) C9 0.0369(12) 0.0363(12) 0.0432(13) -0.0035(9) 0.0011(10) -0.0075(9) C10 0.0423(13) 0.0389(12) 0.0355(12) -0.0022(10) 0.0013(10) -0.0006(10) C11 0.0323(11) 0.0343(11) 0.0263(10) 0.0026(8) 0.0058(8) -0.0001(9) C12 0.0267(10) 0.0315(11) 0.0269(10) 0.0016(8) 0.0024(8) -0.0006(8) C13 0.0306(11) 0.0312(11) 0.0251(10) 0.0017(8) 0.0050(8) 0.0003(8) C14 0.0309(11) 0.0315(11) 0.0311(10) 0.0038(8) 0.0063(9) -0.0009(9) C15 0.0394(12) 0.0308(11) 0.0347(12) 0.0002(9) 0.0070(10) 0.0038(9) C16 0.0537(16) 0.0462(14) 0.0494(15) -0.0099(11) 0.0133(12) -0.0144(12) C17 0.0659(18) 0.0488(16) 0.0599(17) -0.0222(13) 0.0130(14) -0.0100(13) C18 0.0630(17) 0.0535(15) 0.0410(13) -0.0126(11) 0.0084(12) 0.0003(13) C19 0.0516(15) 0.0437(13) 0.0393(12) -0.0084(10) 0.0143(11) 0.0023(11) C20 0.0302(11) 0.0392(12) 0.0317(11) -0.0019(9) 0.0067(9) 0.0057(9) C21 0.0292(11) 0.0383(12) 0.0287(11) 0.0000(9) 0.0066(9) -0.0024(9) C22 0.0322(11) 0.0311(10) 0.0362(12) -0.0024(9) 0.0055(9) 0.0022(9) C23 0.0273(14) 0.083(2) 0.087(2) -0.0051(17) 0.0058(14) -0.0063(13) C24 0.0362(13) 0.0389(12) 0.0364(12) 0.0102(9) 0.0063(10) 0.0015(10) C25 0.0606(19) 0.090(2) 0.0393(15) 0.0031(14) -0.0114(13) -0.0021(16) O1 0.0959(16) 0.0521(11) 0.0573(12) -0.0032(9) 0.0515(12) -0.0112(10) O2 0.0349(9) 0.0482(9) 0.0594(12) -0.0080(8) 0.0039(8) -0.0028(7) O3 0.0444(10) 0.0609(11) 0.0395(10) 0.0100(8) -0.0054(8) 0.0018(8) O4 0.0271(8) 0.0550(10) 0.0555(11) 0.0029(8) 0.0065(7) -0.0031(7) O5 0.0435(11) 0.1106(18) 0.0524(12) 0.0059(11) 0.0025(9) 0.0272(11) O6 0.0425(9) 0.0621(11) 0.0323(8) -0.0015(7) -0.0013(7) 0.0069(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.214(3) . ? C1 C21 1.483(3) . ? C1 C2 1.529(3) . ? C2 C3 1.541(3) . ? C2 C11 1.559(3) . ? C3 O2 1.449(3) . ? C3 C4 1.509(4) . ? C4 C5 1.376(4) . ? C4 C9 1.392(3) . ? C5 C6 1.390(5) . ? C6 C7 1.374(4) . ? C7 C8 1.387(4) . ? C8 C9 1.384(4) . ? C9 C10 1.510(3) . ? C10 O2 1.448(3) . ? C10 C11 1.552(3) . ? C11 C12 1.546(3) . ? C12 C21 1.507(3) . ? C12 C13 1.527(3) . ? C13 C22 1.516(3) . ? C13 C14 1.544(3) . ? C14 C24 1.519(3) . ? C14 C15 1.542(3) . ? C15 C20 1.512(3) . ? C15 C16 1.544(3) . ? C16 C17 1.528(4) . ? C17 C18 1.506(4) . ? C18 C19 1.526(4) . ? C19 C20 1.509(3) . ? C20 C21 1.339(3) . ? C22 O3 1.204(3) . ? C22 O4 1.334(3) . ? C23 O4 1.446(3) . ? C24 O5 1.185(3) . ? C24 O6 1.331(3) . ? C25 O6 1.438(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 O1 C1 C21 128.2(2) . . ? O1 C1 C2 123.3(2) . . ? C21 C1 C2 108.50(18) . . ? C1 C2 C3 112.4(2) . . ? C1 C2 C11 106.47(17) . . ? C3 C2 C11 101.44(18) . . ? O2 C3 C4 101.95(19) . . ? O2 C3 C2 100.64(18) . . ? C4 C3 C2 108.0(2) . . ? C5 C4 C9 120.9(3) . . ? C5 C4 C3 134.3(2) . . ? C9 C4 C3 104.6(2) . . ? C4 C5 C6 117.8(3) . . ? C7 C6 C5 121.6(3) . . ? C6 C7 C8 120.7(3) . . ? C9 C8 C7 118.0(2) . . ? C8 C9 C4 121.0(2) . . ? C8 C9 C10 134.0(2) . . ? C4 C9 C10 104.8(2) . . ? O2 C10 C9 101.30(18) . . ? O2 C10 C11 101.71(17) . . ? C9 C10 C11 106.92(18) . . ? C12 C11 C10 113.71(17) . . ? C12 C11 C2 106.25(16) . . ? C10 C11 C2 100.84(17) . . ? C21 C12 C13 111.02(17) . . ? C21 C12 C11 107.67(16) . . ? C13 C12 C11 116.49(17) . . ? C22 C13 C12 113.91(16) . . ? C22 C13 C14 112.14(16) . . ? C12 C13 C14 107.96(17) . . ? C24 C14 C15 111.52(18) . . ? C24 C14 C13 108.88(17) . . ? C15 C14 C13 113.27(16) . . ? C20 C15 C14 114.91(17) . . ? C20 C15 C16 108.83(18) . . ? C14 C15 C16 111.66(18) . . ? C17 C16 C15 111.9(2) . . ? C18 C17 C16 111.2(2) . . ? C17 C18 C19 112.1(2) . . ? C20 C19 C18 111.6(2) . . ? C21 C20 C19 125.0(2) . . ? C21 C20 C15 121.27(18) . . ? C19 C20 C15 113.68(18) . . ? C20 C21 C1 127.41(19) . . ? C20 C21 C12 123.68(19) . . ? C1 C21 C12 108.52(18) . . ? O3 C22 O4 123.6(2) . . ? O3 C22 C13 126.2(2) . . ? O4 C22 C13 110.21(18) . . ? O5 C24 O6 123.8(2) . . ? O5 C24 C14 126.3(2) . . ? O6 C24 C14 109.97(19) . . ? C10 O2 C3 96.29(17) . . ? C22 O4 C23 116.1(2) . . ? C24 O6 C25 117.9(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.176 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.039 data_4 _database_code_depnum_ccdc_archive 'CCDC 257084' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N O3' _chemical_formula_weight 323.39 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 10.470(4) _cell_length_b 6.352(2) _cell_length_c 24.228(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.129(14) _cell_angle_gamma 90.00 _cell_volume 1604.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour none _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4213 _diffrn_reflns_av_R_equivalents 0.1355 _diffrn_reflns_av_sigmaI/netI 0.1221 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 21.50 _reflns_number_total 1444 _reflns_number_gt 727 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1871P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1444 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1853 _refine_ls_R_factor_gt 0.0913 _refine_ls_wR_factor_ref 0.3265 _refine_ls_wR_factor_gt 0.2502 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.3474(11) -0.0817(19) 0.4050(5) 0.073(3) Uani 1 1 d . . . C2 C 0.2235(10) -0.0561(18) 0.3784(5) 0.085(4) Uani 1 1 d . . . H2 H 0.2200 0.0675 0.3541 0.128 Uiso 1 1 calc R . . C3 C 0.1014(13) -0.049(2) 0.4209(6) 0.110(5) Uani 1 1 d . . . H3 H 0.1144 0.0445 0.4530 0.165 Uiso 1 1 calc R . . C4 C -0.0112(13) -0.019(3) 0.3872(7) 0.124(5) Uani 1 1 d . . . H4 H -0.0635 0.0994 0.3848 0.148 Uiso 1 1 calc R . . C5 C -0.0272(11) -0.195(3) 0.3595(6) 0.108(4) Uani 1 1 d . . . H5 H -0.0968 -0.2203 0.3338 0.129 Uiso 1 1 calc R . . C6 C 0.0764(10) -0.3507(18) 0.3732(4) 0.083(4) Uani 1 1 d . . . H6 H 0.0540 -0.4979 0.3649 0.125 Uiso 1 1 calc R . . C7 C 0.2022(9) -0.2598(19) 0.3441(4) 0.078(3) Uani 1 1 d . . . H7 H 0.1781 -0.2251 0.3052 0.117 Uiso 1 1 calc R . . C8 C 0.0887(10) -0.291(2) 0.4346(5) 0.103(4) Uani 1 1 d . . . H8A H 0.1646 -0.3485 0.4550 0.154 Uiso 1 1 calc R . . H8B H 0.0127 -0.3235 0.4530 0.154 Uiso 1 1 calc R . . C9 C 0.4047(11) -0.2819(17) 0.3885(4) 0.071(3) Uani 1 1 d . . . C10 C 0.5207(11) -0.3658(18) 0.3986(4) 0.075(3) Uani 1 1 d . . . C11 C 0.6164(10) -0.2702(19) 0.4329(4) 0.093(4) Uani 1 1 d . . . H11A H 0.5792 -0.1670 0.4563 0.139 Uiso 1 1 calc R . . H11B H 0.6758 -0.1984 0.4108 0.139 Uiso 1 1 calc R . . C12 C 0.6825(12) -0.429(2) 0.4665(5) 0.107(4) Uani 1 1 d . . . H12A H 0.6429 -0.4347 0.5011 0.161 Uiso 1 1 calc R . . H12B H 0.7697 -0.3797 0.4752 0.161 Uiso 1 1 calc R . . C13 C 0.6902(13) -0.651(2) 0.4454(5) 0.119(5) Uani 1 1 d . . . H13A H 0.7698 -0.7140 0.4608 0.178 Uiso 1 1 calc R . . H13B H 0.6199 -0.7321 0.4579 0.178 Uiso 1 1 calc R . . C14 C 0.6839(11) -0.659(2) 0.3837(5) 0.113(5) Uani 1 1 d . . . H14A H 0.7499 -0.5724 0.3693 0.170 Uiso 1 1 calc R . . H14B H 0.6903 -0.8016 0.3702 0.170 Uiso 1 1 calc R . . C15 C 0.5539(11) -0.5691(17) 0.3699(5) 0.082(4) Uani 1 1 d . . . H15 H 0.4922 -0.6756 0.3798 0.123 Uiso 1 1 calc R . . C16 C 0.5372(11) -0.5463(19) 0.3058(4) 0.081(4) Uani 1 1 d . . . H16 H 0.5368 -0.6857 0.2884 0.122 Uiso 1 1 calc R . . C17 C 0.6343(14) -0.397(2) 0.2782(4) 0.075(3) Uani 1 1 d . . . C18 C 0.4450(14) -0.254(2) 0.2626(5) 0.094(4) Uani 1 1 d . . . C19 C 0.4072(10) -0.4466(19) 0.2953(5) 0.082(4) Uani 1 1 d . . . H19 H 0.3552 -0.5382 0.2697 0.123 Uiso 1 1 calc R . . C20 C 0.3226(10) -0.3977(17) 0.3490(4) 0.073(3) Uani 1 1 d . . . H20 H 0.3015 -0.5323 0.3657 0.110 Uiso 1 1 calc R . . O1 O 0.3860(8) 0.0453(13) 0.4370(4) 0.106(3) Uani 1 1 d . . . O2 O 0.3763(9) -0.119(2) 0.2455(4) 0.164(5) Uani 1 1 d . . . O3 O 0.7521(9) -0.4112(12) 0.2749(3) 0.100(3) Uani 1 1 d . . . N1 N 0.5749(11) -0.2342(18) 0.2561(4) 0.083(3) Uani 1 1 d . . . H1 H 0.613(9) -0.102(15) 0.230(4) 0.08(3) Uiso 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 0.072(8) 0.064(8) 0.079(8) -0.004(7) -0.015(6) 0.004(7) C2 0.068(8) 0.078(8) 0.103(9) -0.001(7) -0.031(7) 0.009(6) C3 0.082(11) 0.135(14) 0.112(11) -0.022(9) 0.000(9) 0.009(9) C4 0.080(11) 0.142(14) 0.141(14) -0.009(11) -0.030(9) 0.019(9) C5 0.057(8) 0.138(13) 0.123(11) 0.012(10) -0.019(7) 0.000(9) C6 0.056(8) 0.095(9) 0.095(9) -0.006(7) -0.015(6) -0.002(7) C7 0.044(7) 0.110(9) 0.076(7) 0.014(7) -0.020(5) 0.001(7) C8 0.068(8) 0.151(14) 0.086(9) 0.010(9) -0.012(6) -0.002(8) C9 0.075(8) 0.061(8) 0.072(7) 0.001(6) -0.021(6) 0.000(7) C10 0.073(8) 0.075(8) 0.072(7) -0.009(6) -0.017(6) 0.005(7) C11 0.077(8) 0.109(10) 0.085(8) -0.001(7) -0.033(6) -0.003(8) C12 0.104(10) 0.100(10) 0.109(10) -0.003(9) -0.040(8) 0.018(8) C13 0.149(12) 0.108(12) 0.088(10) 0.007(8) -0.046(8) 0.041(9) C14 0.087(9) 0.135(12) 0.111(11) -0.003(9) -0.029(7) 0.044(8) C15 0.084(9) 0.063(8) 0.096(9) 0.017(7) -0.011(7) 0.005(6) C16 0.076(9) 0.091(9) 0.070(8) -0.016(7) -0.024(6) 0.012(7) C17 0.069(10) 0.085(10) 0.070(8) -0.013(7) -0.002(7) -0.021(9) C18 0.066(11) 0.131(13) 0.083(9) 0.020(9) -0.002(7) 0.013(10) C19 0.067(8) 0.096(9) 0.077(9) -0.007(7) -0.029(7) -0.022(7) C20 0.061(7) 0.086(8) 0.068(7) 0.002(6) -0.017(6) -0.016(6) O1 0.103(7) 0.098(6) 0.110(7) -0.038(5) -0.029(5) -0.006(5) O2 0.071(7) 0.228(12) 0.192(10) 0.133(10) 0.006(6) 0.031(7) O3 0.063(6) 0.116(7) 0.118(7) 0.004(5) -0.005(5) -0.007(5) N1 0.067(9) 0.091(8) 0.086(7) 0.019(7) -0.013(5) 0.004(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.165(11) . ? C1 C2 1.405(13) . ? C1 C9 1.477(15) . ? C2 C7 1.543(14) . ? C2 C3 1.711(18) . ? C3 C4 1.385(16) . ? C3 C8 1.576(17) . ? C4 C5 1.306(16) . ? C5 C6 1.483(15) . ? C6 C8 1.530(14) . ? C6 C7 1.651(14) . ? C7 C20 1.531(13) . ? C9 C10 1.329(13) . ? C9 C20 1.431(12) . ? C10 C11 1.383(13) . ? C10 C15 1.521(14) . ? C11 C12 1.433(14) . ? C12 C13 1.503(16) . ? C13 C14 1.491(15) . ? C14 C15 1.486(14) . ? C15 C16 1.555(14) . ? C16 C19 1.502(14) . ? C16 C17 1.583(16) . ? C17 O3 1.247(13) . ? C17 N1 1.295(13) . ? C18 O2 1.170(13) . ? C18 N1 1.389(14) . ? C18 C19 1.529(16) . ? C19 C20 1.666(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 118.4(11) . . ? O1 C1 C9 130.6(10) . . ? C2 C1 C9 110.9(11) . . ? C1 C2 C7 103.5(9) . . ? C1 C2 C3 115.8(10) . . ? C7 C2 C3 105.3(9) . . ? C4 C3 C8 100.1(12) . . ? C4 C3 C2 107.0(12) . . ? C8 C3 C2 100.6(10) . . ? C5 C4 C3 104.3(14) . . ? C4 C5 C6 113.5(11) . . ? C5 C6 C8 92.6(10) . . ? C5 C6 C7 105.5(9) . . ? C8 C6 C7 109.0(8) . . ? C20 C7 C2 111.1(7) . . ? C20 C7 C6 116.7(9) . . ? C2 C7 C6 98.4(9) . . ? C6 C8 C3 92.2(10) . . ? C10 C9 C20 113.7(10) . . ? C10 C9 C1 133.0(10) . . ? C20 C9 C1 112.9(10) . . ? C9 C10 C11 122.3(10) . . ? C9 C10 C15 119.9(9) . . ? C11 C10 C15 117.7(10) . . ? C10 C11 C12 108.6(10) . . ? C11 C12 C13 120.2(10) . . ? C14 C13 C12 111.9(11) . . ? C15 C14 C13 99.7(11) . . ? C14 C15 C10 117.6(10) . . ? C14 C15 C16 106.2(10) . . ? C10 C15 C16 111.6(9) . . ? C19 C16 C15 103.1(9) . . ? C19 C16 C17 106.4(10) . . ? C15 C16 C17 117.3(9) . . ? O3 C17 N1 118.3(12) . . ? O3 C17 C16 131.2(12) . . ? N1 C17 C16 110.5(11) . . ? O2 C18 N1 118.0(14) . . ? O2 C18 C19 126.2(13) . . ? N1 C18 C19 115.6(12) . . ? C16 C19 C18 98.8(10) . . ? C16 C19 C20 119.0(9) . . ? C18 C19 C20 115.8(9) . . ? C9 C20 C7 101.5(9) . . ? C9 C20 C19 106.7(8) . . ? C7 C20 C19 122.6(8) . . ? C17 N1 C18 108.7(12) . . ? _diffrn_measured_fraction_theta_max 0.783 _diffrn_reflns_theta_full 21.50 _diffrn_measured_fraction_theta_full 0.783 _refine_diff_density_max 0.304 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.109