# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Yawen Zhang' _publ_contact_author_address ; College of Chemistry and Chemical Engineering, Suzhou University Suzhou University Dushu Lake Higher Education Zone Suzhou 215123 CHINA ; _publ_contact_author_email ZHANGYW@SUDA.EDU.CN _publ_section_title ; Dynamic kinetic resolution of 2-oxo-3-aryl-succinic acid esters by organocatalyzed aldolization ; loop_ _publ_author_name 'Ya-Wen Zhang' 'Bin Li' 'Zongxuan Shen' 'Yajun Wang' 'Yong Zhang' # Attachment 'cif-B.cif' data_shelxl_b _database_code_depnum_ccdc_archive 'CCDC 621996' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 O7' _chemical_formula_sum 'C18 H24 O7' _chemical_formula_weight 352.37 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 5.5529(6) _cell_length_b 14.4502(16) _cell_length_c 22.426(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1799.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 7252 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9443 _exptl_absorpt_correction_T_max 0.9706 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17443 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.35 _reflns_number_total 1929 _reflns_number_gt 1898 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _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^)+(0.0464P)^2^+0.5239P] 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 1929 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 O1 O -0.1468(3) 0.56184(12) 0.33146(7) 0.0311(4) Uani 1 1 d . . . O2 O 0.1149(3) 0.52645(10) 0.25885(6) 0.0243(3) Uani 1 1 d . . . O3 O 0.0010(3) 0.35564(10) 0.37467(6) 0.0234(3) Uani 1 1 d . . . H3 H -0.0699 0.3343 0.3446 0.035 Uiso 1 1 calc R . . O4 O 0.1278(3) 0.31774(10) 0.26415(6) 0.0238(3) Uani 1 1 d . . . O5 O 0.5143(3) 0.36131(9) 0.27935(6) 0.0198(3) Uani 1 1 d . . . O6 O 0.3730(4) 0.19912(10) 0.36397(8) 0.0394(4) Uani 1 1 d . . . O7 O 0.2166(3) 0.66768(9) 0.58463(6) 0.0250(3) Uani 1 1 d . . . C1 C 0.2428(4) 0.49528(13) 0.35646(8) 0.0180(4) Uani 1 1 d . . . H1 H 0.4002 0.5132 0.3381 0.022 Uiso 1 1 calc R . . C2 C 0.0451(4) 0.53199(13) 0.31572(9) 0.0204(4) Uani 1 1 d . . . C3 C -0.0561(4) 0.55952(14) 0.21416(9) 0.0270(5) Uani 1 1 d . . . H3A H -0.0802 0.6271 0.2181 0.032 Uiso 1 1 calc R . . H3B H -0.2136 0.5283 0.2190 0.032 Uiso 1 1 calc R . . C4 C 0.0513(6) 0.53670(18) 0.15468(10) 0.0428(7) Uani 1 1 d . . . H4A H 0.2076 0.5676 0.1507 0.064 Uiso 1 1 calc R . . H4B H -0.0568 0.5580 0.1230 0.064 Uiso 1 1 calc R . . H4C H 0.0733 0.4696 0.1514 0.064 Uiso 1 1 calc R . . C5 C 0.2349(4) 0.38675(14) 0.35808(8) 0.0186(4) Uani 1 1 d . . . C6 C 0.2849(4) 0.34974(13) 0.29499(9) 0.0183(4) Uani 1 1 d . . . C7 C 0.5744(4) 0.33268(14) 0.21853(8) 0.0224(4) Uani 1 1 d . . . H7A H 0.7260 0.3631 0.2060 0.027 Uiso 1 1 calc R . . H7B H 0.4452 0.3529 0.1910 0.027 Uiso 1 1 calc R . . C8 C 0.6034(4) 0.22930(15) 0.21444(10) 0.0292(5) Uani 1 1 d . . . H8A H 0.7230 0.2087 0.2437 0.044 Uiso 1 1 calc R . . H8B H 0.6575 0.2126 0.1743 0.044 Uiso 1 1 calc R . . H8C H 0.4486 0.1993 0.2227 0.044 Uiso 1 1 calc R . . C9 C 0.4173(4) 0.35152(13) 0.40342(8) 0.0204(4) Uani 1 1 d . . . H9A H 0.5727 0.3833 0.3964 0.025 Uiso 1 1 calc R . . H9B H 0.3614 0.3687 0.4439 0.025 Uiso 1 1 calc R . . C10 C 0.4594(4) 0.24827(14) 0.40177(9) 0.0253(5) Uani 1 1 d . . . C11 C 0.6251(5) 0.21028(16) 0.44906(10) 0.0323(5) Uani 1 1 d . . . H11A H 0.5996 0.1434 0.4529 0.048 Uiso 1 1 calc R . . H11B H 0.5907 0.2405 0.4872 0.048 Uiso 1 1 calc R . . H11C H 0.7927 0.2222 0.4377 0.048 Uiso 1 1 calc R . . C12 C 0.2332(4) 0.54010(13) 0.41775(8) 0.0185(4) Uani 1 1 d . . . C13 C 0.0434(4) 0.52636(14) 0.45803(9) 0.0216(4) Uani 1 1 d . . . H13 H -0.0874 0.4874 0.4473 0.026 Uiso 1 1 calc R . . C14 C 0.0451(4) 0.56895(14) 0.51318(9) 0.0215(4) Uani 1 1 d . . . H14 H -0.0834 0.5582 0.5403 0.026 Uiso 1 1 calc R . . C15 C 0.2338(4) 0.62765(13) 0.52950(8) 0.0198(4) Uani 1 1 d . . . C16 C 0.4220(4) 0.64288(14) 0.48975(9) 0.0225(4) Uani 1 1 d . . . H16 H 0.5504 0.6833 0.5000 0.027 Uiso 1 1 calc R . . C17 C 0.4205(4) 0.59820(13) 0.43468(9) 0.0211(4) Uani 1 1 d . . . H17 H 0.5510 0.6077 0.4080 0.025 Uiso 1 1 calc R . . C18 C 0.4137(4) 0.72480(15) 0.60301(10) 0.0290(5) Uani 1 1 d . . . H18A H 0.5631 0.6887 0.6019 0.044 Uiso 1 1 calc R . . H18B H 0.3854 0.7469 0.6437 0.044 Uiso 1 1 calc R . . H18C H 0.4276 0.7779 0.5760 0.044 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 0.0217(8) 0.0460(9) 0.0257(8) -0.0018(7) 0.0004(7) 0.0113(8) O2 0.0262(8) 0.0274(7) 0.0193(7) 0.0018(6) 0.0000(6) 0.0052(7) O3 0.0149(7) 0.0276(7) 0.0277(7) -0.0037(6) 0.0032(6) -0.0051(6) O4 0.0188(7) 0.0272(7) 0.0253(7) -0.0047(6) -0.0037(6) -0.0011(7) O5 0.0158(7) 0.0233(7) 0.0203(7) -0.0051(6) 0.0015(6) -0.0007(6) O6 0.0518(11) 0.0245(7) 0.0419(9) -0.0032(7) -0.0171(9) 0.0015(9) O7 0.0269(8) 0.0297(7) 0.0184(7) -0.0046(6) 0.0015(6) -0.0022(7) C1 0.0140(9) 0.0199(9) 0.0200(9) 0.0006(8) 0.0031(9) 0.0000(8) C2 0.0212(11) 0.0194(9) 0.0206(9) -0.0029(8) -0.0002(9) -0.0013(9) C3 0.0318(12) 0.0253(10) 0.0239(10) 0.0016(8) -0.0072(10) 0.0053(10) C4 0.0567(18) 0.0477(14) 0.0239(11) 0.0013(10) -0.0040(12) 0.0154(15) C5 0.0140(10) 0.0213(9) 0.0206(9) -0.0017(8) 0.0009(9) -0.0012(9) C6 0.0154(9) 0.0166(9) 0.0230(10) 0.0000(8) -0.0020(9) 0.0021(8) C7 0.0206(10) 0.0293(10) 0.0174(9) -0.0035(8) 0.0023(8) -0.0012(10) C8 0.0257(12) 0.0297(11) 0.0321(11) -0.0081(9) 0.0032(11) 0.0004(10) C9 0.0178(10) 0.0242(9) 0.0193(9) 0.0001(8) 0.0008(8) -0.0005(9) C10 0.0246(11) 0.0264(10) 0.0249(10) 0.0032(9) 0.0026(10) -0.0001(9) C11 0.0328(13) 0.0338(12) 0.0303(11) 0.0059(9) -0.0037(11) 0.0059(11) C12 0.0170(10) 0.0181(8) 0.0204(9) 0.0003(7) 0.0001(8) 0.0030(8) C13 0.0186(10) 0.0222(9) 0.0241(9) -0.0023(8) 0.0006(9) -0.0015(9) C14 0.0191(10) 0.0259(10) 0.0195(9) 0.0002(8) 0.0042(9) -0.0001(9) C15 0.0215(10) 0.0193(9) 0.0186(9) -0.0007(7) -0.0014(8) 0.0038(9) C16 0.0215(11) 0.0224(9) 0.0238(9) -0.0019(8) -0.0024(9) -0.0031(9) C17 0.0178(10) 0.0242(10) 0.0214(9) 0.0002(8) 0.0026(9) 0.0000(9) C18 0.0322(13) 0.0310(11) 0.0239(10) -0.0067(9) -0.0012(10) -0.0051(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 O1 C2 1.203(3) . ? O2 C2 1.335(2) . ? O2 C3 1.461(2) . ? O3 C5 1.424(2) . ? O3 H3 0.8400 . ? O4 C6 1.205(2) . ? O5 C6 1.332(3) . ? O5 C7 1.464(2) . ? O6 C10 1.205(3) . ? O7 C15 1.368(2) . ? O7 C18 1.432(3) . ? C1 C12 1.520(3) . ? C1 C2 1.523(3) . ? C1 C5 1.569(3) . ? C1 H1 1.0000 . ? C3 C4 1.498(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C9 1.523(3) . ? C5 C6 1.538(3) . ? C7 C8 1.505(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.511(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.507(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C17 1.389(3) . ? C12 C13 1.402(3) . ? C13 C14 1.381(3) . ? C13 H13 0.9500 . ? C14 C15 1.397(3) . ? C14 H14 0.9500 . ? C15 C16 1.391(3) . ? C16 C17 1.394(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 C3 116.55(17) . . ? C5 O3 H3 109.5 . . ? C6 O5 C7 115.35(16) . . ? C15 O7 C18 116.76(17) . . ? C12 C1 C2 111.63(16) . . ? C12 C1 C5 113.82(15) . . ? C2 C1 C5 109.97(16) . . ? C12 C1 H1 107.0 . . ? C2 C1 H1 107.0 . . ? C5 C1 H1 107.0 . . ? O1 C2 O2 124.0(2) . . ? O1 C2 C1 125.96(18) . . ? O2 C2 C1 110.05(17) . . ? O2 C3 C4 106.27(19) . . ? O2 C3 H3A 110.5 . . ? C4 C3 H3A 110.5 . . ? O2 C3 H3B 110.5 . . ? C4 C3 H3B 110.5 . . ? H3A C3 H3B 108.7 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O3 C5 C9 109.06(15) . . ? O3 C5 C6 107.18(16) . . ? C9 C5 C6 112.21(16) . . ? O3 C5 C1 110.32(16) . . ? C9 C5 C1 109.32(16) . . ? C6 C5 C1 108.74(15) . . ? O4 C6 O5 126.08(18) . . ? O4 C6 C5 122.06(18) . . ? O5 C6 C5 111.80(17) . . ? O5 C7 C8 111.19(17) . . ? O5 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? O5 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C5 114.63(17) . . ? C10 C9 H9A 108.6 . . ? C5 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C5 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? O6 C10 C11 121.53(19) . . ? O6 C10 C9 122.5(2) . . ? C11 C10 C9 115.91(18) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 118.17(18) . . ? C17 C12 C1 118.57(18) . . ? C13 C12 C1 123.26(18) . . ? C14 C13 C12 120.6(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.67(19) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? O7 C15 C16 124.39(19) . . ? O7 C15 C14 116.16(18) . . ? C16 C15 C14 119.45(17) . . ? C15 C16 C17 119.33(19) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C12 C17 C16 121.79(19) . . ? C12 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? O7 C18 H18A 109.5 . . ? O7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C3 O2 C2 O1 0.2(3) . . . . ? C3 O2 C2 C1 -179.81(15) . . . . ? C12 C1 C2 O1 -27.8(3) . . . . ? C5 C1 C2 O1 99.5(2) . . . . ? C12 C1 C2 O2 152.24(16) . . . . ? C5 C1 C2 O2 -80.4(2) . . . . ? C2 O2 C3 C4 -174.01(19) . . . . ? C12 C1 C5 O3 71.4(2) . . . . ? C2 C1 C5 O3 -54.7(2) . . . . ? C12 C1 C5 C9 -48.5(2) . . . . ? C2 C1 C5 C9 -174.64(16) . . . . ? C12 C1 C5 C6 -171.35(16) . . . . ? C2 C1 C5 C6 62.5(2) . . . . ? C7 O5 C6 O4 0.7(3) . . . . ? C7 O5 C6 C5 -176.67(15) . . . . ? O3 C5 C6 O4 13.3(2) . . . . ? C9 C5 C6 O4 133.0(2) . . . . ? C1 C5 C6 O4 -105.9(2) . . . . ? O3 C5 C6 O5 -169.16(15) . . . . ? C9 C5 C6 O5 -49.5(2) . . . . ? C1 C5 C6 O5 71.6(2) . . . . ? C6 O5 C7 C8 -79.0(2) . . . . ? O3 C5 C9 C10 69.5(2) . . . . ? C6 C5 C9 C10 -49.1(2) . . . . ? C1 C5 C9 C10 -169.77(17) . . . . ? C5 C9 C10 O6 6.7(3) . . . . ? C5 C9 C10 C11 -175.66(18) . . . . ? C2 C1 C12 C17 -112.8(2) . . . . ? C5 C1 C12 C17 122.0(2) . . . . ? C2 C1 C12 C13 66.7(2) . . . . ? C5 C1 C12 C13 -58.6(3) . . . . ? C17 C12 C13 C14 -0.6(3) . . . . ? C1 C12 C13 C14 179.91(18) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? C18 O7 C15 C16 -3.6(3) . . . . ? C18 O7 C15 C14 177.34(18) . . . . ? C13 C14 C15 O7 178.90(18) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? O7 C15 C16 C17 -179.98(18) . . . . ? C14 C15 C16 C17 -0.9(3) . . . . ? C13 C12 C17 C16 -0.6(3) . . . . ? C1 C12 C17 C16 178.93(17) . . . . ? C15 C16 C17 C12 1.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C17 H17 O1 0.95 2.49 3.378(3) 155.5 1_655 C7 H7B O7 0.99 2.57 3.410(2) 143.0 4_564 O3 H3 O4 0.84 2.13 2.634(2) 118.8 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.173 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.039 # Attachment 'cif-A.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 621997' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H25 Cl O6' _chemical_formula_sum 'C27 H25 Cl O6' _chemical_formula_weight 480.92 _chemical_absolute_configuration ad 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.7585(11) _cell_length_b 12.377(2) _cell_length_c 17.297(3) _cell_angle_alpha 97.499(19) _cell_angle_beta 97.56(2) _cell_angle_gamma 103.09(2) _cell_volume 1173.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 4457 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8787 _exptl_absorpt_correction_T_max 0.9899 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11389 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0822 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.35 _reflns_number_total 7036 _reflns_number_gt 5326 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _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^)+(0.0507P)^2^+0.4578P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.13(9) _refine_ls_number_reflns 7036 _refine_ls_number_parameters 618 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1555 _refine_ls_wR_factor_gt 0.1378 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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 Cl1 Cl 0.3154(3) 0.70280(14) 0.84106(10) 0.0496(4) Uani 1 1 d . . . Cl2 Cl 0.2476(3) 0.69921(14) 0.33851(10) 0.0530(5) Uani 1 1 d . . . O1 O 0.4751(7) 1.0287(3) 0.7219(3) 0.0462(11) Uani 1 1 d . . . O2 O 0.2235(6) 0.9231(3) 0.6163(2) 0.0320(9) Uani 1 1 d . . . O3 O 0.6740(7) 0.8247(3) 0.5933(2) 0.0345(9) Uani 1 1 d . . . H3 H 0.8122 0.8291 0.6166 0.052 Uiso 1 1 calc R . . O4 O 0.4933(9) 0.5721(4) 0.5085(3) 0.0570(12) Uani 1 1 d . . . O5 O 0.8337(6) 0.6753(3) 0.6702(2) 0.0400(10) Uani 1 1 d . . . O6 O 0.4552(6) 0.5895(3) 0.6847(2) 0.0338(9) Uani 1 1 d . . . O7 O 0.0710(7) 0.8611(3) 0.0950(2) 0.0408(10) Uani 1 1 d . . . O8 O 0.3651(7) 0.9861(3) 0.1793(2) 0.0418(10) Uani 1 1 d . . . O9 O 0.5728(6) 0.7820(3) 0.0774(2) 0.0358(9) Uani 1 1 d . . . H9 H 0.7149 0.7860 0.0967 0.054 Uiso 1 1 calc R . . O10 O 0.4408(10) 0.5274(4) 0.0102(3) 0.0664(14) Uani 1 1 d . . . O11 O 0.7630(7) 0.6496(3) 0.1678(2) 0.0415(10) Uani 1 1 d . . . O12 O 0.3945(6) 0.5611(3) 0.1869(2) 0.0374(10) Uani 1 1 d . . . C1 C 0.6280(10) 0.8493(4) 0.7741(3) 0.0323(13) Uani 1 1 d . . . C2 C 0.5910(11) 0.7954(5) 0.8397(3) 0.0386(14) Uani 1 1 d . . . C3 C 0.7738(11) 0.8127(5) 0.9052(4) 0.0427(15) Uani 1 1 d . . . H3A H 0.7468 0.7755 0.9484 0.051 Uiso 1 1 calc R . . C4 C 0.9940(12) 0.8851(6) 0.9052(4) 0.0487(16) Uani 1 1 d . . . H4 H 1.1175 0.8974 0.9491 0.058 Uiso 1 1 calc R . . C5 C 1.0367(11) 0.9395(5) 0.8426(4) 0.0436(15) Uani 1 1 d . . . H5 H 1.1881 0.9886 0.8435 0.052 Uiso 1 1 calc R . . C6 C 0.8567(10) 0.9218(5) 0.7783(3) 0.0378(14) Uani 1 1 d . . . H6 H 0.8878 0.9597 0.7356 0.045 Uiso 1 1 calc R . . C7 C 0.3880(10) 0.9386(5) 0.6814(3) 0.0313(13) Uani 1 1 d . . . C8 C 0.4359(9) 0.8281(4) 0.7008(3) 0.0285(12) Uani 1 1 d . . . H8 H 0.2842 0.7837 0.7136 0.034 Uiso 1 1 calc R . . C9 C 0.1596(10) 1.0252(5) 0.5981(4) 0.0384(14) Uani 1 1 d . . . H9A H 0.1453 1.0705 0.6473 0.046 Uiso 1 1 calc R . . H9B H 0.0012 1.0047 0.5639 0.046 Uiso 1 1 calc R . . C10 C 0.3422(10) 1.0961(5) 0.5574(3) 0.0359(14) Uani 1 1 d . . . C11 C 0.3416(11) 1.2078(5) 0.5581(3) 0.0407(15) Uani 1 1 d . . . H11 H 0.2336 1.2386 0.5848 0.049 Uiso 1 1 calc R . . C12 C 0.5018(12) 1.2751(5) 0.5192(4) 0.0493(17) Uani 1 1 d . . . H12 H 0.5015 1.3511 0.5201 0.059 Uiso 1 1 calc R . . C13 C 0.6580(11) 1.2309(5) 0.4800(4) 0.0486(17) Uani 1 1 d . . . H13 H 0.7666 1.2766 0.4545 0.058 Uiso 1 1 calc R . . C14 C 0.6564(11) 1.1182(5) 0.4780(4) 0.0471(16) Uani 1 1 d . . . H14 H 0.7616 1.0868 0.4502 0.057 Uiso 1 1 calc R . . C15 C 0.4996(10) 1.0528(5) 0.5171(4) 0.0409(15) Uani 1 1 d . . . H15 H 0.5004 0.9767 0.5161 0.049 Uiso 1 1 calc R . . C16 C 0.5019(9) 0.7548(4) 0.6286(3) 0.0277(12) Uani 1 1 d . . . C17 C 0.2790(9) 0.6971(4) 0.5660(3) 0.0311(13) Uani 1 1 d . . . H17A H 0.1411 0.6747 0.5931 0.037 Uiso 1 1 calc R . . H17B H 0.2430 0.7524 0.5335 0.037 Uiso 1 1 calc R . . C18 C 0.2995(11) 0.5947(5) 0.5116(3) 0.0403(14) Uani 1 1 d . . . C19 C 0.0670(11) 0.5224(6) 0.4654(4) 0.058(2) Uani 1 1 d . . . H19A H 0.1000 0.4719 0.4227 0.087 Uiso 1 1 calc R . . H19B H -0.0297 0.5694 0.4435 0.087 Uiso 1 1 calc R . . H19C H -0.0207 0.4788 0.4998 0.087 Uiso 1 1 calc R . . C20 C 0.6200(9) 0.6686(4) 0.6618(3) 0.0292(12) Uani 1 1 d . . . C21 C 0.5520(10) 0.5100(5) 0.7250(4) 0.0444(16) Uani 1 1 d . . . H21A H 0.6487 0.5482 0.7762 0.053 Uiso 1 1 calc R . . H21B H 0.6571 0.4781 0.6933 0.053 Uiso 1 1 calc R . . C22 C 0.3488(10) 0.4183(4) 0.7370(3) 0.0332(13) Uani 1 1 d . . . C23 C 0.1144(11) 0.4002(5) 0.6973(4) 0.0395(14) Uani 1 1 d . . . H23 H 0.0771 0.4498 0.6635 0.047 Uiso 1 1 calc R . . C24 C -0.0662(11) 0.3093(5) 0.7067(4) 0.0462(16) Uani 1 1 d . . . H24 H -0.2242 0.2977 0.6792 0.055 Uiso 1 1 calc R . . C25 C -0.0143(11) 0.2362(5) 0.7563(4) 0.0438(15) Uani 1 1 d . . . H25 H -0.1371 0.1750 0.7626 0.053 Uiso 1 1 calc R . . C26 C 0.2132(12) 0.2522(5) 0.7961(4) 0.0493(17) Uani 1 1 d . . . H26 H 0.2480 0.2024 0.8300 0.059 Uiso 1 1 calc R . . C27 C 0.3985(12) 0.3442(5) 0.7865(4) 0.0433(15) Uani 1 1 d . . . H27 H 0.5563 0.3549 0.8139 0.052 Uiso 1 1 calc R . . C28 C 0.5356(10) 0.8322(5) 0.2571(3) 0.0333(13) Uani 1 1 d . . . C29 C 0.5170(11) 0.7916(5) 0.3273(3) 0.0379(14) Uani 1 1 d . . . C30 C 0.7021(12) 0.8180(5) 0.3906(4) 0.0458(16) Uani 1 1 d . . . H30 H 0.6832 0.7876 0.4370 0.055 Uiso 1 1 calc R . . C31 C 0.9177(12) 0.8909(6) 0.3841(4) 0.0527(18) Uani 1 1 d . . . H31 H 1.0464 0.9104 0.4269 0.063 Uiso 1 1 calc R . . C32 C 0.9456(11) 0.9347(5) 0.3163(4) 0.0457(16) Uani 1 1 d . . . H32 H 1.0931 0.9835 0.3126 0.055 Uiso 1 1 calc R . . C33 C 0.7567(11) 0.9071(5) 0.2534(3) 0.0397(14) Uani 1 1 d . . . H33 H 0.7760 0.9387 0.2074 0.048 Uiso 1 1 calc R . . C34 C 0.3385(9) 0.7925(4) 0.1846(3) 0.0278(12) Uani 1 1 d . . . H34 H 0.1991 0.7446 0.2019 0.033 Uiso 1 1 calc R . . C35 C 0.2431(10) 0.8807(5) 0.1472(3) 0.0324(13) Uani 1 1 d . . . C36 C 0.2772(12) 1.0750(5) 0.1452(4) 0.0451(15) Uani 1 1 d . . . H36A H 0.2983 1.1398 0.1870 0.054 Uiso 1 1 calc R . . H36B H 0.1039 1.0473 0.1245 0.054 Uiso 1 1 calc R . . C37 C 0.4090(10) 1.1127(4) 0.0793(3) 0.0370(14) Uani 1 1 d . . . C38 C 0.3804(12) 1.2114(5) 0.0549(4) 0.0500(17) Uani 1 1 d . . . H38 H 0.2778 1.2502 0.0782 0.060 Uiso 1 1 calc R . . C39 C 0.4982(14) 1.2540(6) -0.0026(4) 0.061(2) Uani 1 1 d . . . H39 H 0.4810 1.3226 -0.0173 0.074 Uiso 1 1 calc R . . C40 C 0.6449(13) 1.1936(6) -0.0390(4) 0.060(2) Uani 1 1 d . . . H40 H 0.7237 1.2203 -0.0796 0.072 Uiso 1 1 calc R . . C41 C 0.6719(13) 1.0955(6) -0.0147(4) 0.0545(18) Uani 1 1 d . . . H41 H 0.7723 1.0557 -0.0385 0.065 Uiso 1 1 calc R . . C42 C 0.5559(11) 1.0538(5) 0.0435(4) 0.0477(16) Uani 1 1 d . . . H42 H 0.5756 0.9860 0.0591 0.057 Uiso 1 1 calc R . . C43 C 0.4150(9) 0.7148(4) 0.1178(3) 0.0292(12) Uani 1 1 d . . . C44 C 0.1965(10) 0.6457(5) 0.0561(3) 0.0360(14) Uani 1 1 d . . . H44A H 0.0657 0.6146 0.0839 0.043 Uiso 1 1 calc R . . H44B H 0.1392 0.6965 0.0234 0.043 Uiso 1 1 calc R . . C45 C 0.2462(13) 0.5507(5) 0.0025(4) 0.0484(17) Uani 1 1 d . . . C46 C 0.0357(13) 0.4865(6) -0.0591(4) 0.066(2) Uani 1 1 d . . . H46A H 0.0879 0.4337 -0.0953 0.099 Uiso 1 1 calc R . . H46B H -0.0276 0.5384 -0.0882 0.099 Uiso 1 1 calc R . . H46C H -0.0895 0.4458 -0.0339 0.099 Uiso 1 1 calc R . . C47 C 0.5461(10) 0.6394(4) 0.1585(3) 0.0317(13) Uani 1 1 d . . . C48 C 0.5004(11) 0.4899(5) 0.2330(4) 0.0484(17) Uani 1 1 d . . . H48A H 0.5972 0.5345 0.2825 0.058 Uiso 1 1 calc R . . H48B H 0.6064 0.4553 0.2034 0.058 Uiso 1 1 calc R . . C49 C 0.2990(10) 0.4001(5) 0.2504(3) 0.0369(14) Uani 1 1 d . . . C50 C 0.0709(11) 0.3709(5) 0.2059(4) 0.0483(17) Uani 1 1 d . . . H50 H 0.0362 0.4090 0.1639 0.058 Uiso 1 1 calc R . . C51 C -0.1096(11) 0.2848(5) 0.2228(4) 0.0518(18) Uani 1 1 d . . . H51 H -0.2657 0.2657 0.1927 0.062 Uiso 1 1 calc R . . C52 C -0.0575(13) 0.2282(5) 0.2836(4) 0.0504(17) Uani 1 1 d . . . H52 H -0.1769 0.1692 0.2946 0.060 Uiso 1 1 calc R . . C53 C 0.1664(13) 0.2577(6) 0.3276(4) 0.0545(18) Uani 1 1 d . . . H53 H 0.2006 0.2196 0.3696 0.065 Uiso 1 1 calc R . . C54 C 0.3474(11) 0.3437(5) 0.3118(4) 0.0463(16) Uani 1 1 d . . . H54 H 0.5021 0.3632 0.3429 0.056 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 Cl1 0.0511(11) 0.0575(10) 0.0497(10) 0.0214(8) 0.0262(9) 0.0155(8) Cl2 0.0535(11) 0.0723(11) 0.0441(9) 0.0263(8) 0.0230(9) 0.0199(9) O1 0.043(2) 0.034(2) 0.059(3) 0.003(2) 0.000(2) 0.014(2) O2 0.030(2) 0.035(2) 0.038(2) 0.0113(17) 0.0079(18) 0.0158(17) O3 0.031(2) 0.042(2) 0.037(2) 0.0149(18) 0.0142(18) 0.0122(18) O4 0.063(3) 0.061(3) 0.058(3) 0.005(2) 0.018(3) 0.037(3) O5 0.026(2) 0.050(2) 0.053(3) 0.022(2) 0.0147(19) 0.0163(19) O6 0.028(2) 0.036(2) 0.046(2) 0.0201(18) 0.0138(18) 0.0146(17) O7 0.034(2) 0.050(2) 0.039(2) 0.012(2) 0.003(2) 0.0119(19) O8 0.041(2) 0.041(2) 0.048(3) 0.013(2) 0.013(2) 0.0150(19) O9 0.030(2) 0.048(2) 0.037(2) 0.0182(19) 0.0183(19) 0.0101(19) O10 0.063(3) 0.074(3) 0.065(3) -0.009(3) 0.008(3) 0.035(3) O11 0.024(2) 0.054(3) 0.051(3) 0.015(2) 0.0103(18) 0.0139(18) O12 0.031(2) 0.042(2) 0.048(3) 0.020(2) 0.0126(19) 0.0157(18) C1 0.031(3) 0.037(3) 0.034(3) 0.008(3) 0.012(3) 0.015(3) C2 0.044(4) 0.039(3) 0.038(3) 0.006(3) 0.017(3) 0.015(3) C3 0.049(4) 0.054(4) 0.036(3) 0.014(3) 0.013(3) 0.027(3) C4 0.047(4) 0.069(4) 0.036(4) 0.002(3) 0.006(3) 0.030(4) C5 0.034(3) 0.052(4) 0.044(4) 0.001(3) 0.005(3) 0.013(3) C6 0.035(3) 0.045(3) 0.038(3) 0.005(3) 0.008(3) 0.019(3) C7 0.030(3) 0.035(3) 0.034(3) 0.010(3) 0.014(3) 0.011(3) C8 0.022(3) 0.038(3) 0.032(3) 0.008(2) 0.013(2) 0.013(2) C9 0.030(3) 0.047(3) 0.050(4) 0.018(3) 0.017(3) 0.022(3) C10 0.038(3) 0.037(3) 0.039(3) 0.013(3) 0.011(3) 0.016(3) C11 0.044(4) 0.043(3) 0.041(4) 0.009(3) 0.013(3) 0.018(3) C12 0.059(4) 0.044(4) 0.053(4) 0.022(3) 0.015(4) 0.019(3) C13 0.047(4) 0.044(4) 0.060(4) 0.029(3) 0.013(3) 0.007(3) C14 0.037(3) 0.064(4) 0.054(4) 0.023(3) 0.026(3) 0.024(3) C15 0.038(3) 0.044(3) 0.047(4) 0.010(3) 0.018(3) 0.015(3) C16 0.024(3) 0.031(3) 0.033(3) 0.010(2) 0.016(2) 0.008(2) C17 0.026(3) 0.031(3) 0.038(3) 0.005(3) 0.007(3) 0.010(2) C18 0.048(4) 0.039(3) 0.036(3) 0.008(3) 0.012(3) 0.012(3) C19 0.051(4) 0.051(4) 0.058(5) -0.003(4) 0.014(4) -0.012(3) C20 0.025(3) 0.032(3) 0.033(3) 0.009(2) 0.011(2) 0.007(2) C21 0.032(3) 0.047(4) 0.066(4) 0.032(3) 0.018(3) 0.017(3) C22 0.029(3) 0.030(3) 0.046(3) 0.011(3) 0.012(3) 0.013(2) C23 0.042(4) 0.041(3) 0.045(4) 0.017(3) 0.013(3) 0.022(3) C24 0.031(3) 0.052(4) 0.055(4) 0.012(3) 0.003(3) 0.010(3) C25 0.037(3) 0.042(3) 0.051(4) 0.007(3) 0.007(3) 0.008(3) C26 0.062(5) 0.040(4) 0.046(4) 0.017(3) 0.004(3) 0.011(3) C27 0.044(4) 0.041(3) 0.052(4) 0.018(3) 0.010(3) 0.019(3) C28 0.032(3) 0.042(3) 0.029(3) 0.004(3) 0.009(3) 0.014(3) C29 0.042(4) 0.045(3) 0.034(3) 0.008(3) 0.015(3) 0.020(3) C30 0.051(4) 0.058(4) 0.036(4) 0.010(3) 0.006(3) 0.028(3) C31 0.046(4) 0.077(5) 0.035(4) -0.005(3) -0.005(3) 0.029(4) C32 0.028(3) 0.056(4) 0.050(4) -0.001(3) 0.001(3) 0.013(3) C33 0.039(3) 0.047(3) 0.039(3) 0.009(3) 0.015(3) 0.018(3) C34 0.021(3) 0.037(3) 0.028(3) 0.010(2) 0.009(2) 0.008(2) C35 0.029(3) 0.037(3) 0.033(3) 0.009(3) 0.013(3) 0.006(3) C36 0.054(4) 0.039(3) 0.050(4) 0.010(3) 0.013(3) 0.021(3) C37 0.040(3) 0.031(3) 0.042(4) 0.005(3) 0.008(3) 0.014(3) C38 0.065(4) 0.044(4) 0.057(4) 0.018(3) 0.020(4) 0.033(3) C39 0.078(5) 0.052(4) 0.066(5) 0.025(4) 0.006(4) 0.036(4) C40 0.075(5) 0.059(4) 0.057(5) 0.027(4) 0.020(4) 0.022(4) C41 0.061(4) 0.051(4) 0.063(5) 0.014(4) 0.029(4) 0.025(4) C42 0.045(4) 0.043(3) 0.058(4) 0.013(3) 0.009(3) 0.016(3) C43 0.023(3) 0.039(3) 0.030(3) 0.009(3) 0.014(2) 0.010(2) C44 0.026(3) 0.053(4) 0.029(3) 0.001(3) 0.005(2) 0.013(3) C45 0.063(5) 0.049(4) 0.030(3) 0.001(3) 0.012(3) 0.009(4) C46 0.062(5) 0.070(5) 0.054(5) -0.002(4) 0.011(4) -0.001(4) C47 0.032(3) 0.032(3) 0.036(3) 0.006(3) 0.014(3) 0.011(2) C48 0.034(3) 0.053(4) 0.069(5) 0.033(4) 0.014(3) 0.016(3) C49 0.038(3) 0.036(3) 0.042(3) 0.018(3) 0.012(3) 0.012(3) C50 0.039(4) 0.056(4) 0.052(4) 0.023(3) -0.003(3) 0.015(3) C51 0.028(3) 0.049(4) 0.074(5) 0.015(4) 0.002(3) 0.001(3) C52 0.055(4) 0.045(4) 0.056(4) 0.013(3) 0.015(4) 0.016(3) C53 0.059(5) 0.057(4) 0.049(4) 0.018(3) 0.008(4) 0.013(4) C54 0.039(4) 0.039(3) 0.058(4) 0.013(3) 0.005(3) 0.004(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 Cl1 C2 1.740(6) . ? Cl2 C29 1.756(6) . ? O1 C7 1.199(6) . ? O2 C7 1.335(6) . ? O2 C9 1.455(6) . ? O3 C16 1.418(6) . ? O3 H3 0.8300 . ? O4 C18 1.216(7) . ? O5 C20 1.202(6) . ? O6 C20 1.341(6) . ? O6 C21 1.446(6) . ? O7 C35 1.207(6) . ? O8 C35 1.340(6) . ? O8 C36 1.468(7) . ? O9 C43 1.409(6) . ? O9 H9 0.8300 . ? O10 C45 1.214(8) . ? O11 C47 1.213(6) . ? O12 C47 1.341(6) . ? O12 C48 1.443(7) . ? C1 C6 1.403(7) . ? C1 C2 1.404(8) . ? C1 C8 1.521(7) . ? C2 C3 1.399(8) . ? C3 C4 1.377(9) . ? C3 H3A 0.9400 . ? C4 C5 1.369(9) . ? C4 H4 0.9400 . ? C5 C6 1.374(8) . ? C5 H5 0.9400 . ? C6 H6 0.9400 . ? C7 C8 1.525(7) . ? C8 C16 1.585(7) . ? C8 H8 0.9900 . ? C9 C10 1.519(7) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C10 C15 1.373(8) . ? C10 C11 1.381(7) . ? C11 C12 1.400(8) . ? C11 H11 0.9400 . ? C12 C13 1.361(9) . ? C12 H12 0.9400 . ? C13 C14 1.389(8) . ? C13 H13 0.9400 . ? C14 C15 1.378(8) . ? C14 H14 0.9400 . ? C15 H15 0.9400 . ? C16 C20 1.522(7) . ? C16 C17 1.532(7) . ? C17 C18 1.514(8) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 C19 1.491(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C21 C22 1.491(7) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C22 C27 1.384(8) . ? C22 C23 1.387(8) . ? C23 C24 1.392(8) . ? C23 H23 0.9400 . ? C24 C25 1.380(8) . ? C24 H24 0.9400 . ? C25 C26 1.356(8) . ? C25 H25 0.9400 . ? C26 C27 1.417(8) . ? C26 H26 0.9400 . ? C27 H27 0.9400 . ? C28 C29 1.383(8) . ? C28 C33 1.409(8) . ? C28 C34 1.521(7) . ? C29 C30 1.371(8) . ? C30 C31 1.386(9) . ? C30 H30 0.9400 . ? C31 C32 1.368(9) . ? C31 H31 0.9400 . ? C32 C33 1.381(8) . ? C32 H32 0.9400 . ? C33 H33 0.9400 . ? C34 C35 1.507(7) . ? C34 C43 1.578(7) . ? C34 H34 0.9900 . ? C36 C37 1.517(8) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C37 C38 1.381(8) . ? C37 C42 1.389(8) . ? C38 C39 1.370(9) . ? C38 H38 0.9400 . ? C39 C40 1.404(10) . ? C39 H39 0.9400 . ? C40 C41 1.371(9) . ? C40 H40 0.9400 . ? C41 C42 1.373(9) . ? C41 H41 0.9400 . ? C42 H42 0.9400 . ? C43 C47 1.512(7) . ? C43 C44 1.542(7) . ? C44 C45 1.503(8) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C45 C46 1.497(9) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C46 H46C 0.9700 . ? C48 C49 1.506(8) . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C49 C54 1.376(8) . ? C49 C50 1.377(8) . ? C50 C51 1.401(8) . ? C50 H50 0.9400 . ? C51 C52 1.376(9) . ? C51 H51 0.9400 . ? C52 C53 1.353(9) . ? C52 H52 0.9400 . ? C53 C54 1.394(9) . ? C53 H53 0.9400 . ? C54 H54 0.9400 . ? 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 C7 O2 C9 114.3(4) . . ? C16 O3 H3 109.5 . . ? C20 O6 C21 115.1(4) . . ? C35 O8 C36 115.2(5) . . ? C43 O9 H9 109.5 . . ? C47 O12 C48 117.1(4) . . ? C6 C1 C2 116.4(5) . . ? C6 C1 C8 121.0(5) . . ? C2 C1 C8 122.6(5) . . ? C3 C2 C1 121.6(5) . . ? C3 C2 Cl1 117.8(4) . . ? C1 C2 Cl1 120.6(5) . . ? C4 C3 C2 118.9(6) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C5 C4 C3 121.3(6) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 119.6(6) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 122.3(6) . . ? C5 C6 H6 118.8 . . ? C1 C6 H6 118.8 . . ? O1 C7 O2 123.1(5) . . ? O1 C7 C8 124.6(5) . . ? O2 C7 C8 112.2(4) . . ? C1 C8 C7 110.7(4) . . ? C1 C8 C16 111.5(4) . . ? C7 C8 C16 113.1(4) . . ? C1 C8 H8 107.1 . . ? C7 C8 H8 107.1 . . ? C16 C8 H8 107.1 . . ? O2 C9 C10 113.4(4) . . ? O2 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? O2 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C15 C10 C11 118.8(5) . . ? C15 C10 C9 122.9(5) . . ? C11 C10 C9 118.3(5) . . ? C10 C11 C12 120.1(6) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.3(6) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.7(6) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 119.5(6) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C10 C15 C14 121.5(6) . . ? C10 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? O3 C16 C20 107.9(4) . . ? O3 C16 C17 109.2(4) . . ? C20 C16 C17 111.0(4) . . ? O3 C16 C8 109.4(4) . . ? C20 C16 C8 107.3(4) . . ? C17 C16 C8 112.0(4) . . ? C18 C17 C16 115.9(5) . . ? C18 C17 H17A 108.3 . . ? C16 C17 H17A 108.3 . . ? C18 C17 H17B 108.3 . . ? C16 C17 H17B 108.3 . . ? H17A C17 H17B 107.4 . . ? O4 C18 C19 123.0(6) . . ? O4 C18 C17 121.4(5) . . ? C19 C18 C17 115.5(6) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O5 C20 O6 125.3(5) . . ? O5 C20 C16 124.0(5) . . ? O6 C20 C16 110.5(4) . . ? O6 C21 C22 109.3(5) . . ? O6 C21 H21A 109.8 . . ? C22 C21 H21A 109.8 . . ? O6 C21 H21B 109.8 . . ? C22 C21 H21B 109.8 . . ? H21A C21 H21B 108.3 . . ? C27 C22 C23 118.4(5) . . ? C27 C22 C21 118.7(5) . . ? C23 C22 C21 122.8(5) . . ? C22 C23 C24 120.7(5) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C25 C24 C23 120.2(6) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C26 C25 C24 120.2(6) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C27 119.9(6) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C22 C27 C26 120.5(6) . . ? C22 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C29 C28 C33 116.4(5) . . ? C29 C28 C34 122.7(5) . . ? C33 C28 C34 120.6(5) . . ? C30 C29 C28 123.4(6) . . ? C30 C29 Cl2 116.5(5) . . ? C28 C29 Cl2 120.1(5) . . ? C29 C30 C31 118.3(6) . . ? C29 C30 H30 120.9 . . ? C31 C30 H30 120.9 . . ? C32 C31 C30 120.9(6) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C31 C32 C33 119.9(6) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? C32 C33 C28 121.0(6) . . ? C32 C33 H33 119.5 . . ? C28 C33 H33 119.5 . . ? C35 C34 C28 117.7(4) . . ? C35 C34 C43 108.1(4) . . ? C28 C34 C43 111.8(4) . . ? C35 C34 H34 106.2 . . ? C28 C34 H34 106.2 . . ? C43 C34 H34 106.2 . . ? O7 C35 O8 122.0(5) . . ? O7 C35 C34 124.7(5) . . ? O8 C35 C34 113.3(5) . . ? O8 C36 C37 112.3(5) . . ? O8 C36 H36A 109.1 . . ? C37 C36 H36A 109.1 . . ? O8 C36 H36B 109.1 . . ? C37 C36 H36B 109.1 . . ? H36A C36 H36B 107.9 . . ? C38 C37 C42 119.3(6) . . ? C38 C37 C36 117.2(5) . . ? C42 C37 C36 123.5(5) . . ? C39 C38 C37 121.5(6) . . ? C39 C38 H38 119.3 . . ? C37 C38 H38 119.3 . . ? C38 C39 C40 119.0(6) . . ? C38 C39 H39 120.5 . . ? C40 C39 H39 120.5 . . ? C41 C40 C39 119.2(7) . . ? C41 C40 H40 120.4 . . ? C39 C40 H40 120.4 . . ? C40 C41 C42 121.6(7) . . ? C40 C41 H41 119.2 . . ? C42 C41 H41 119.2 . . ? C41 C42 C37 119.4(6) . . ? C41 C42 H42 120.3 . . ? C37 C42 H42 120.3 . . ? O9 C43 C47 109.5(4) . . ? O9 C43 C44 107.3(4) . . ? C47 C43 C44 111.4(5) . . ? O9 C43 C34 109.4(4) . . ? C47 C43 C34 107.0(4) . . ? C44 C43 C34 112.2(4) . . ? C45 C44 C43 114.9(5) . . ? C45 C44 H44A 108.5 . . ? C43 C44 H44A 108.5 . . ? C45 C44 H44B 108.5 . . ? C43 C44 H44B 108.5 . . ? H44A C44 H44B 107.5 . . ? O10 C45 C46 123.2(6) . . ? O10 C45 C44 122.2(6) . . ? C46 C45 C44 114.6(6) . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? O11 C47 O12 122.9(5) . . ? O11 C47 C43 125.2(5) . . ? O12 C47 C43 111.8(4) . . ? O12 C48 C49 108.3(5) . . ? O12 C48 H48A 110.0 . . ? C49 C48 H48A 110.0 . . ? O12 C48 H48B 110.0 . . ? C49 C48 H48B 110.0 . . ? H48A C48 H48B 108.4 . . ? C54 C49 C50 119.3(5) . . ? C54 C49 C48 118.6(6) . . ? C50 C49 C48 122.1(5) . . ? C49 C50 C51 120.3(6) . . ? C49 C50 H50 119.8 . . ? C51 C50 H50 119.8 . . ? C52 C51 C50 119.7(6) . . ? C52 C51 H51 120.1 . . ? C50 C51 H51 120.1 . . ? C53 C52 C51 119.7(6) . . ? C53 C52 H52 120.2 . . ? C51 C52 H52 120.2 . . ? C52 C53 C54 121.2(7) . . ? C52 C53 H53 119.4 . . ? C54 C53 H53 119.4 . . ? C49 C54 C53 119.8(6) . . ? C49 C54 H54 120.1 . . ? C53 C54 H54 120.1 . . ? 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 -0.6(8) . . . . ? C8 C1 C2 C3 177.3(5) . . . . ? C6 C1 C2 Cl1 -179.6(4) . . . . ? C8 C1 C2 Cl1 -1.6(7) . . . . ? C1 C2 C3 C4 0.6(9) . . . . ? Cl1 C2 C3 C4 179.6(5) . . . . ? C2 C3 C4 C5 -0.3(9) . . . . ? C3 C4 C5 C6 0.1(9) . . . . ? C4 C5 C6 C1 -0.1(9) . . . . ? C2 C1 C6 C5 0.4(8) . . . . ? C8 C1 C6 C5 -177.6(5) . . . . ? C9 O2 C7 O1 0.4(7) . . . . ? C9 O2 C7 C8 176.2(4) . . . . ? C6 C1 C8 C7 -55.8(6) . . . . ? C2 C1 C8 C7 126.3(5) . . . . ? C6 C1 C8 C16 71.0(6) . . . . ? C2 C1 C8 C16 -106.8(6) . . . . ? O1 C7 C8 C1 -5.5(7) . . . . ? O2 C7 C8 C1 178.7(4) . . . . ? O1 C7 C8 C16 -131.5(6) . . . . ? O2 C7 C8 C16 52.7(6) . . . . ? C7 O2 C9 C10 80.2(6) . . . . ? O2 C9 C10 C15 21.8(8) . . . . ? O2 C9 C10 C11 -161.2(5) . . . . ? C15 C10 C11 C12 -0.9(9) . . . . ? C9 C10 C11 C12 -178.0(5) . . . . ? C10 C11 C12 C13 0.3(10) . . . . ? C11 C12 C13 C14 0.7(10) . . . . ? C12 C13 C14 C15 -1.3(10) . . . . ? C11 C10 C15 C14 0.3(9) . . . . ? C9 C10 C15 C14 177.3(6) . . . . ? C13 C14 C15 C10 0.7(10) . . . . ? C1 C8 C16 O3 -79.8(5) . . . . ? C7 C8 C16 O3 45.7(6) . . . . ? C1 C8 C16 C20 37.0(6) . . . . ? C7 C8 C16 C20 162.5(4) . . . . ? C1 C8 C16 C17 159.1(4) . . . . ? C7 C8 C16 C17 -75.4(5) . . . . ? O3 C16 C17 C18 80.4(6) . . . . ? C20 C16 C17 C18 -38.4(6) . . . . ? C8 C16 C17 C18 -158.3(4) . . . . ? C16 C17 C18 O4 -12.7(8) . . . . ? C16 C17 C18 C19 165.0(5) . . . . ? C21 O6 C20 O5 2.2(8) . . . . ? C21 O6 C20 C16 -173.7(5) . . . . ? O3 C16 C20 O5 13.8(7) . . . . ? C17 C16 C20 O5 133.3(6) . . . . ? C8 C16 C20 O5 -104.0(6) . . . . ? O3 C16 C20 O6 -170.3(4) . . . . ? C17 C16 C20 O6 -50.7(6) . . . . ? C8 C16 C20 O6 72.0(5) . . . . ? C20 O6 C21 C22 -172.2(5) . . . . ? O6 C21 C22 C27 -168.8(5) . . . . ? O6 C21 C22 C23 15.1(8) . . . . ? C27 C22 C23 C24 -0.2(9) . . . . ? C21 C22 C23 C24 175.9(6) . . . . ? C22 C23 C24 C25 0.4(10) . . . . ? C23 C24 C25 C26 -0.2(10) . . . . ? C24 C25 C26 C27 -0.2(10) . . . . ? C23 C22 C27 C26 -0.2(9) . . . . ? C21 C22 C27 C26 -176.4(6) . . . . ? C25 C26 C27 C22 0.4(10) . . . . ? C33 C28 C29 C30 -1.9(9) . . . . ? C34 C28 C29 C30 173.4(5) . . . . ? C33 C28 C29 Cl2 179.2(4) . . . . ? C34 C28 C29 Cl2 -5.5(8) . . . . ? C28 C29 C30 C31 1.2(9) . . . . ? Cl2 C29 C30 C31 -179.9(5) . . . . ? C29 C30 C31 C32 -0.4(10) . . . . ? C30 C31 C32 C33 0.5(10) . . . . ? C31 C32 C33 C28 -1.3(9) . . . . ? C29 C28 C33 C32 2.0(8) . . . . ? C34 C28 C33 C32 -173.4(5) . . . . ? C29 C28 C34 C35 126.5(6) . . . . ? C33 C28 C34 C35 -58.4(7) . . . . ? C29 C28 C34 C43 -107.5(6) . . . . ? C33 C28 C34 C43 67.6(6) . . . . ? C36 O8 C35 O7 -1.2(7) . . . . ? C36 O8 C35 C34 -179.5(5) . . . . ? C28 C34 C35 O7 -171.9(5) . . . . ? C43 C34 C35 O7 60.3(6) . . . . ? C28 C34 C35 O8 6.3(6) . . . . ? C43 C34 C35 O8 -121.5(5) . . . . ? C35 O8 C36 C37 -93.0(6) . . . . ? O8 C36 C37 C38 -166.1(5) . . . . ? O8 C36 C37 C42 13.4(8) . . . . ? C42 C37 C38 C39 -1.6(10) . . . . ? C36 C37 C38 C39 177.9(6) . . . . ? C37 C38 C39 C40 2.1(11) . . . . ? C38 C39 C40 C41 -1.8(11) . . . . ? C39 C40 C41 C42 1.1(11) . . . . ? C40 C41 C42 C37 -0.5(10) . . . . ? C38 C37 C42 C41 0.7(9) . . . . ? C36 C37 C42 C41 -178.7(6) . . . . ? C35 C34 C43 O9 52.6(5) . . . . ? C28 C34 C43 O9 -78.5(5) . . . . ? C35 C34 C43 C47 171.1(4) . . . . ? C28 C34 C43 C47 40.0(5) . . . . ? C35 C34 C43 C44 -66.3(5) . . . . ? C28 C34 C43 C44 162.6(4) . . . . ? O9 C43 C44 C45 73.8(6) . . . . ? C47 C43 C44 C45 -46.0(6) . . . . ? C34 C43 C44 C45 -166.0(5) . . . . ? C43 C44 C45 O10 3.4(9) . . . . ? C43 C44 C45 C46 -177.9(5) . . . . ? C48 O12 C47 O11 2.5(8) . . . . ? C48 O12 C47 C43 -174.9(5) . . . . ? O9 C43 C47 O11 13.0(8) . . . . ? C44 C43 C47 O11 131.4(6) . . . . ? C34 C43 C47 O11 -105.5(6) . . . . ? O9 C43 C47 O12 -169.8(4) . . . . ? C44 C43 C47 O12 -51.3(6) . . . . ? C34 C43 C47 O12 71.8(5) . . . . ? C47 O12 C48 C49 -173.3(5) . . . . ? O12 C48 C49 C54 -160.9(6) . . . . ? O12 C48 C49 C50 20.8(9) . . . . ? C54 C49 C50 C51 0.0(10) . . . . ? C48 C49 C50 C51 178.3(6) . . . . ? C49 C50 C51 C52 -0.8(10) . . . . ? C50 C51 C52 C53 1.3(11) . . . . ? C51 C52 C53 C54 -0.9(11) . . . . ? C50 C49 C54 C53 0.4(10) . . . . ? C48 C49 C54 C53 -177.9(6) . . . . ? C52 C53 C54 C49 0.1(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O9 H9 O11 0.83 2.26 2.714(5) 114.7 . O9 H9 O7 0.83 2.06 2.775(5) 144.6 1_655 O3 H3 O2 0.83 2.39 3.075(5) 140.1 1_655 O3 H3 O5 0.83 2.24 2.669(5) 112.0 . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.229 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.058