# 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 'Jun-An Ma' _publ_contact_author_address ; Department of Chemistry, Tianjin University Tianjin 300072, CHINA ; _publ_contact_author_email 'MAJUN AN68@TJU.EDU.CN' _publ_section_title ; Stereoselective Construction of Fluorinated Indanone Derivatives via a Triple Cascade Lewis Acid-Catalyzed Reaction ; loop_ _publ_author_name 'Jun-An Ma.' 'Han-Feng Cui.' 'Ke-Yan Dong.' 'Lian Wang.' 'Guang-Wu Zhang.' # Attachment 'CCDC635729.cif' data_061017b _database_code_depnum_ccdc_archive 'CCDC 635729' _audit_creation_date 2007-03-08 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H12 Cl F O3' _chemical_formula_sum 'C17 H12 Cl F O3' _chemical_formula_weight 318.72 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' F F 0.0171 0.0103 '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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 17.213(4) _cell_length_b 8.458(2) _cell_length_c 10.468(2) _cell_angle_alpha 90.0 _cell_angle_beta 96.925(4) _cell_angle_gamma 90.0 _cell_volume 1512.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2162 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 24.15 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method none _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker AXS (2004)' _exptl_absorpt_correction_T_min 0.9375 _exptl_absorpt_correction_T_max 0.9733 _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 8209 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3082 _reflns_number_gt 1861 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART software Bruker' _computing_cell_refinement 'SMART software Bruker' _computing_data_reduction 'SAINT software Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _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^)+(0.0465P)^2^+0.2026P] 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_number_reflns 3082 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 -0.03335(4) 0.31214(10) 0.15135(7) 0.0808(3) Uani 1 1 d . . . F1 F 0.34796(8) 0.68745(15) 0.35412(12) 0.0660(4) Uani 1 1 d . . . O1 O 0.43292(10) 0.62506(19) 0.59974(17) 0.0737(5) Uani 1 1 d . . . O2 O 0.22179(10) 0.7557(2) 0.46457(16) 0.0685(5) Uani 1 1 d . . . O3 O 0.23896(9) 0.53836(18) 0.58835(14) 0.0567(4) Uani 1 1 d . . . C1 C 0.32419(12) 0.5695(2) 0.43420(19) 0.0450(5) Uani 1 1 d . . . C2 C 0.30558(12) 0.4147(2) 0.35799(19) 0.0452(5) Uani 1 1 d . . . H2 H 0.3333 0.4214 0.2818 0.054 Uiso 1 1 calc R . . C3 C 0.22048(12) 0.3873(2) 0.30895(18) 0.0428(5) Uani 1 1 d . . . C4 C 0.18933(13) 0.4530(3) 0.19187(19) 0.0512(6) Uani 1 1 d . . . H4 H 0.2216 0.5114 0.1444 0.061 Uiso 1 1 calc R . . C5 C 0.11163(14) 0.4331(3) 0.1451(2) 0.0567(6) Uani 1 1 d . . . H5 H 0.0915 0.4790 0.0674 0.068 Uiso 1 1 calc R . . C6 C 0.06430(13) 0.3451(3) 0.2138(2) 0.0523(6) Uani 1 1 d . . . C7 C 0.09256(13) 0.2803(3) 0.3304(2) 0.0571(6) Uani 1 1 d . . . H7 H 0.0598 0.2225 0.3773 0.069 Uiso 1 1 calc R . . C8 C 0.17048(13) 0.3021(3) 0.3773(2) 0.0520(6) Uani 1 1 d . . . H8 H 0.1897 0.2586 0.4564 0.062 Uiso 1 1 calc R . . C9 C 0.34746(11) 0.2890(2) 0.44404(19) 0.0447(5) Uani 1 1 d . . . C10 C 0.34445(14) 0.1262(3) 0.4292(2) 0.0596(6) Uani 1 1 d . . . H10 H 0.3110 0.0802 0.3632 0.072 Uiso 1 1 calc R . . C11 C 0.39200(14) 0.0336(3) 0.5143(3) 0.0648(7) Uani 1 1 d . . . H11 H 0.3903 -0.0758 0.5052 0.078 Uiso 1 1 calc R . . C12 C 0.44226(13) 0.1002(3) 0.6133(2) 0.0612(6) Uani 1 1 d . . . H12 H 0.4738 0.0353 0.6694 0.073 Uiso 1 1 calc R . . C13 C 0.44577(12) 0.2605(3) 0.6290(2) 0.0550(6) Uani 1 1 d . . . H13 H 0.4795 0.3055 0.6951 0.066 Uiso 1 1 calc R . . C14 C 0.39789(12) 0.3546(2) 0.5442(2) 0.0447(5) Uani 1 1 d . . . C15 C 0.39279(13) 0.5268(3) 0.5391(2) 0.0496(5) Uani 1 1 d . . . C16 C 0.25561(13) 0.6357(3) 0.4955(2) 0.0472(5) Uani 1 1 d . . . C17 C 0.17179(16) 0.5783(3) 0.6533(3) 0.0754(8) Uani 1 1 d . . . H17A H 0.1266 0.5912 0.5909 0.113 Uiso 1 1 calc R . . H17B H 0.1819 0.6752 0.7002 0.113 Uiso 1 1 calc R . . H17C H 0.1624 0.4951 0.7119 0.113 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 0.0516(4) 0.1091(6) 0.0778(5) 0.0013(4) -0.0087(3) 0.0021(4) F1 0.0758(9) 0.0507(8) 0.0737(9) 0.0111(7) 0.0182(7) -0.0124(7) O1 0.0694(11) 0.0527(10) 0.0930(13) -0.0118(10) -0.0152(10) -0.0128(9) O2 0.0791(12) 0.0525(10) 0.0743(11) 0.0078(9) 0.0104(9) 0.0198(9) O3 0.0608(10) 0.0552(10) 0.0568(9) 0.0056(8) 0.0188(7) 0.0081(8) C1 0.0494(12) 0.0364(11) 0.0503(12) 0.0054(10) 0.0103(9) -0.0049(10) C2 0.0482(12) 0.0472(12) 0.0418(11) -0.0046(10) 0.0118(9) -0.0039(10) C3 0.0512(13) 0.0388(11) 0.0386(11) -0.0056(9) 0.0071(9) 0.0000(10) C4 0.0630(15) 0.0496(14) 0.0415(12) 0.0009(10) 0.0091(10) -0.0045(11) C5 0.0665(16) 0.0603(15) 0.0411(12) 0.0033(11) -0.0025(11) 0.0084(12) C6 0.0469(12) 0.0573(14) 0.0508(13) -0.0038(12) -0.0013(10) 0.0040(11) C7 0.0503(13) 0.0649(15) 0.0558(14) 0.0115(12) 0.0049(10) -0.0044(12) C8 0.0501(13) 0.0597(14) 0.0453(12) 0.0108(11) 0.0029(10) -0.0033(11) C9 0.0392(11) 0.0441(13) 0.0520(12) -0.0037(10) 0.0110(9) -0.0004(10) C10 0.0529(14) 0.0459(14) 0.0794(17) -0.0155(13) 0.0055(12) -0.0005(11) C11 0.0554(15) 0.0408(13) 0.100(2) -0.0022(14) 0.0164(14) 0.0059(12) C12 0.0486(14) 0.0569(16) 0.0787(17) 0.0134(14) 0.0098(12) 0.0104(12) C13 0.0446(12) 0.0553(15) 0.0644(14) 0.0003(12) 0.0042(10) 0.0015(11) C14 0.0388(11) 0.0427(12) 0.0531(12) -0.0014(10) 0.0077(9) -0.0010(10) C15 0.0457(12) 0.0467(13) 0.0563(13) -0.0040(11) 0.0059(10) -0.0078(11) C16 0.0536(13) 0.0411(12) 0.0454(12) -0.0037(11) -0.0002(10) 0.0004(11) C17 0.0726(18) 0.0844(19) 0.0746(17) -0.0004(15) 0.0309(14) 0.0082(15) _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 C6 1.751(2) . y F1 C1 1.395(2) . y O1 C15 1.210(2) . y O2 C16 1.195(2) . y O3 C16 1.331(2) . y O3 C17 1.450(3) . y C1 C16 1.517(3) . y C1 C2 1.547(3) . y C1 C15 1.555(3) . y C2 C3 1.511(3) . y C2 C9 1.518(3) . y C2 H2 0.9800 . N C3 C8 1.386(3) . y C3 C4 1.393(3) . y C4 C5 1.378(3) . y C4 H4 0.9300 . N C5 C6 1.370(3) . y C5 H5 0.9300 . N C6 C7 1.372(3) . y C7 C8 1.384(3) . y C7 H7 0.9300 . N C8 H8 0.9300 . N C9 C10 1.386(3) . y C9 C14 1.393(3) . y C10 C11 1.379(3) . y C10 H10 0.9300 . N C11 C12 1.387(3) . y C11 H11 0.9300 . N C12 C13 1.366(3) . y C12 H12 0.9300 . N C13 C14 1.388(3) . y C13 H13 0.9300 . N C14 C15 1.460(3) . y C17 H17A 0.9600 . N C17 H17B 0.9600 . N C17 H17C 0.9600 . N 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 C16 O3 C17 116.89(18) . . y F1 C1 C16 106.86(16) . . y F1 C1 C2 110.65(16) . . y C16 C1 C2 114.03(17) . . y F1 C1 C15 109.72(16) . . y C16 C1 C15 110.52(17) . . y C2 C1 C15 105.06(16) . . y C3 C2 C9 117.75(17) . . y C3 C2 C1 115.94(17) . . y C9 C2 C1 103.47(16) . . y C3 C2 H2 106.3 . . N C9 C2 H2 106.3 . . N C1 C2 H2 106.3 . . N C8 C3 C4 117.7(2) . . y C8 C3 C2 122.80(18) . . y C4 C3 C2 119.50(18) . . y C5 C4 C3 121.2(2) . . y C5 C4 H4 119.4 . . N C3 C4 H4 119.4 . . N C6 C5 C4 119.5(2) . . y C6 C5 H5 120.2 . . N C4 C5 H5 120.2 . . N C5 C6 C7 121.0(2) . . y C5 C6 Cl1 119.70(17) . . y C7 C6 Cl1 119.33(18) . . y C6 C7 C8 119.1(2) . . y C6 C7 H7 120.4 . . N C8 C7 H7 120.4 . . N C7 C8 C3 121.5(2) . . y C7 C8 H8 119.3 . . N C3 C8 H8 119.3 . . N C10 C9 C14 119.4(2) . . y C10 C9 C2 128.37(19) . . y C14 C9 C2 112.06(18) . . y C11 C10 C9 118.7(2) . . y C11 C10 H10 120.6 . . N C9 C10 H10 120.6 . . N C10 C11 C12 121.3(2) . . y C10 C11 H11 119.3 . . N C12 C11 H11 119.3 . . N C13 C12 C11 120.5(2) . . y C13 C12 H12 119.7 . . N C11 C12 H12 119.7 . . N C12 C13 C14 118.6(2) . . y C12 C13 H13 120.7 . . N C14 C13 H13 120.7 . . N C13 C14 C9 121.4(2) . . y C13 C14 C15 128.6(2) . . y C9 C14 C15 109.93(19) . . y O1 C15 C14 129.6(2) . . y O1 C15 C1 123.2(2) . . y C14 C15 C1 107.15(17) . . y O2 C16 O3 125.6(2) . . y O2 C16 C1 125.2(2) . . y O3 C16 C1 109.14(17) . . y O3 C17 H17A 109.5 . . N O3 C17 H17B 109.5 . . N H17A C17 H17B 109.5 . . N O3 C17 H17C 109.5 . . N H17A C17 H17C 109.5 . . N H17B C17 H17C 109.5 . . N 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 F1 C1 C2 C3 -96.4(2) . . . . y C16 C1 C2 C3 24.1(2) . . . . y C15 C1 C2 C3 145.24(17) . . . . y F1 C1 C2 C9 133.13(16) . . . . y C16 C1 C2 C9 -106.38(19) . . . . y C15 C1 C2 C9 14.8(2) . . . . y C9 C2 C3 C8 30.2(3) . . . . y C1 C2 C3 C8 -93.0(2) . . . . y C9 C2 C3 C4 -151.54(19) . . . . y C1 C2 C3 C4 85.2(2) . . . . y C8 C3 C4 C5 -0.5(3) . . . . y C2 C3 C4 C5 -178.8(2) . . . . y C3 C4 C5 C6 -1.0(3) . . . . y C4 C5 C6 C7 1.9(3) . . . . y C4 C5 C6 Cl1 -177.17(17) . . . . y C5 C6 C7 C8 -1.3(3) . . . . y Cl1 C6 C7 C8 177.78(18) . . . . y C6 C7 C8 C3 -0.2(4) . . . . y C4 C3 C8 C7 1.1(3) . . . . y C2 C3 C8 C7 179.3(2) . . . . y C3 C2 C9 C10 43.7(3) . . . . y C1 C2 C9 C10 173.1(2) . . . . y C3 C2 C9 C14 -140.49(18) . . . . y C1 C2 C9 C14 -11.1(2) . . . . y C14 C9 C10 C11 -0.3(3) . . . . y C2 C9 C10 C11 175.3(2) . . . . y C9 C10 C11 C12 -0.1(4) . . . . y C10 C11 C12 C13 0.1(4) . . . . y C11 C12 C13 C14 0.2(3) . . . . y C12 C13 C14 C9 -0.5(3) . . . . y C12 C13 C14 C15 -178.1(2) . . . . y C10 C9 C14 C13 0.5(3) . . . . y C2 C9 C14 C13 -175.67(18) . . . . y C10 C9 C14 C15 178.53(19) . . . . y C2 C9 C14 C15 2.3(2) . . . . y C13 C14 C15 O1 6.7(4) . . . . y C9 C14 C15 O1 -171.1(2) . . . . y C13 C14 C15 C1 -174.6(2) . . . . y C9 C14 C15 C1 7.6(2) . . . . y F1 C1 C15 O1 45.7(3) . . . . y C16 C1 C15 O1 -71.9(3) . . . . y C2 C1 C15 O1 164.6(2) . . . . y F1 C1 C15 C14 -133.11(17) . . . . y C16 C1 C15 C14 109.3(2) . . . . y C2 C1 C15 C14 -14.1(2) . . . . y C17 O3 C16 O2 2.9(3) . . . . y C17 O3 C16 C1 -176.68(18) . . . . y F1 C1 C16 O2 10.5(3) . . . . y C2 C1 C16 O2 -112.1(2) . . . . y C15 C1 C16 O2 129.9(2) . . . . y F1 C1 C16 O3 -169.89(16) . . . . y C2 C1 C16 O3 67.5(2) . . . . y C15 C1 C16 O3 -50.6(2) . . . . y _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.167 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.040 # Attachment 'CCDC635730.cif' data_061229c _database_code_depnum_ccdc_archive 'CCDC 635730' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H13 Cl O3' _chemical_formula_sum 'C17 H13 Cl O3' _chemical_formula_weight 300.72 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 16.228(4) _cell_length_b 8.599(2) _cell_length_c 10.594(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.122(5) _cell_angle_gamma 90.00 _cell_volume 1463.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1576 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 23.43 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9386 _exptl_absorpt_correction_T_max 0.9737 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 8103 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.0657 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 26.36 _reflns_number_total 2968 _reflns_number_gt 1669 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method none _refine_ls_number_reflns 2968 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0998 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.002 _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 0.16511(3) 1.21663(7) 0.18877(6) 0.0536(2) Uani 1 1 d . . . O1 O 0.08171(8) 1.14031(17) -0.08646(15) 0.0534(4) Uani 1 1 d . . . O2 O 0.31301(10) 1.23968(19) 0.06181(17) 0.0698(5) Uani 1 1 d . . . O3 O 0.28240(8) 1.03888(17) -0.07074(14) 0.0497(4) Uani 1 1 d . . . C1 C 0.19468(12) 1.0727(2) 0.08289(18) 0.0348(5) Uani 1 1 d . . . C2 C 0.21110(11) 0.9137(2) 0.15320(19) 0.0340(5) Uani 1 1 d . . . H2 H 0.1803 0.9170 0.2263 0.041 Uiso 1 1 calc R . . C3 C 0.30110(12) 0.8832(2) 0.2070(2) 0.0365(5) Uani 1 1 d . . . C4 C 0.33134(13) 0.9429(3) 0.3261(2) 0.0507(6) Uani 1 1 d . . . H4 H 0.2956 0.9963 0.3720 0.061 Uiso 1 1 calc R . . C5 C 0.41383(16) 0.9243(3) 0.3776(2) 0.0660(7) Uani 1 1 d . . . H5 H 0.4335 0.9664 0.4570 0.079 Uiso 1 1 calc R . . C6 C 0.46662(15) 0.8438(3) 0.3114(3) 0.0671(8) Uani 1 1 d . . . H6 H 0.5220 0.8302 0.3463 0.081 Uiso 1 1 calc R . . C7 C 0.43799(14) 0.7836(3) 0.1945(3) 0.0638(7) Uani 1 1 d . . . H7 H 0.4742 0.7294 0.1497 0.077 Uiso 1 1 calc R . . C8 C 0.35524(13) 0.8023(3) 0.1414(2) 0.0498(6) Uani 1 1 d . . . H8 H 0.3363 0.7604 0.0616 0.060 Uiso 1 1 calc R . . C9 C 0.16612(11) 0.7976(2) 0.06038(19) 0.0347(5) Uani 1 1 d . . . C10 C 0.16549(13) 0.6365(3) 0.0679(2) 0.0473(6) Uani 1 1 d . . . H10 H 0.1999 0.5851 0.1324 0.057 Uiso 1 1 calc R . . C11 C 0.11286(13) 0.5537(3) -0.0221(2) 0.0538(6) Uani 1 1 d . . . H11 H 0.1117 0.4457 -0.0171 0.065 Uiso 1 1 calc R . . C12 C 0.06173(13) 0.6284(3) -0.1195(2) 0.0508(6) Uani 1 1 d . . . H12 H 0.0272 0.5702 -0.1792 0.061 Uiso 1 1 calc R . . C13 C 0.06183(12) 0.7871(3) -0.1283(2) 0.0437(5) Uani 1 1 d . . . H13 H 0.0276 0.8377 -0.1934 0.052 Uiso 1 1 calc R . . C14 C 0.11427(12) 0.8711(2) -0.0378(2) 0.0357(5) Uani 1 1 d . . . C15 C 0.12222(12) 1.0399(3) -0.0260(2) 0.0379(5) Uani 1 1 d . . . C16 C 0.27073(13) 1.1312(3) 0.0261(2) 0.0408(5) Uani 1 1 d . . . C17 C 0.35530(14) 1.0712(3) -0.1325(2) 0.0705(8) Uani 1 1 d . . . H17A H 0.3488 1.1703 -0.1744 0.106 Uiso 1 1 calc R . . H17B H 0.3611 0.9916 -0.1942 0.106 Uiso 1 1 calc R . . H17C H 0.4041 1.0730 -0.0696 0.106 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 0.0601(4) 0.0451(4) 0.0556(4) -0.0124(3) 0.0079(3) 0.0072(3) O1 0.0522(10) 0.0445(10) 0.0596(11) 0.0115(8) -0.0054(8) 0.0081(8) O2 0.0687(12) 0.0635(13) 0.0792(13) -0.0125(10) 0.0170(10) -0.0328(10) O3 0.0456(10) 0.0546(11) 0.0521(10) -0.0025(8) 0.0180(8) -0.0041(7) C1 0.0379(13) 0.0283(13) 0.0382(13) -0.0015(10) 0.0047(10) 0.0015(9) C2 0.0342(12) 0.0359(13) 0.0319(12) 0.0029(10) 0.0043(10) -0.0010(9) C3 0.0353(13) 0.0363(13) 0.0364(13) 0.0050(11) 0.0000(11) -0.0044(10) C4 0.0451(15) 0.0612(17) 0.0441(15) 0.0004(13) 0.0001(12) -0.0067(12) C5 0.0528(18) 0.089(2) 0.0501(16) 0.0010(15) -0.0121(14) -0.0187(15) C6 0.0384(16) 0.078(2) 0.078(2) 0.0159(17) -0.0158(15) -0.0067(14) C7 0.0435(16) 0.0626(18) 0.085(2) -0.0028(16) 0.0065(15) 0.0042(13) C8 0.0418(15) 0.0501(16) 0.0550(15) -0.0033(13) -0.0013(12) 0.0022(11) C9 0.0317(12) 0.0347(14) 0.0378(13) 0.0009(11) 0.0059(10) -0.0033(10) C10 0.0423(14) 0.0390(16) 0.0578(16) 0.0090(12) -0.0025(12) -0.0012(11) C11 0.0517(15) 0.0354(15) 0.0747(18) -0.0034(14) 0.0102(14) -0.0092(12) C12 0.0411(14) 0.0509(18) 0.0586(17) -0.0126(13) 0.0008(12) -0.0097(12) C13 0.0343(13) 0.0503(16) 0.0446(14) -0.0003(12) -0.0007(11) -0.0025(11) C14 0.0307(12) 0.0371(14) 0.0387(13) 0.0014(11) 0.0035(10) -0.0024(10) C15 0.0342(13) 0.0426(16) 0.0377(13) 0.0022(11) 0.0078(11) -0.0003(10) C16 0.0403(14) 0.0374(15) 0.0433(14) 0.0062(12) 0.0014(11) -0.0020(11) C17 0.0518(16) 0.089(2) 0.0786(19) 0.0035(16) 0.0355(15) -0.0017(14) _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 C1 1.781(2) . y O1 C15 1.212(2) . y O2 C16 1.187(2) . y O3 C16 1.332(2) . y O3 C17 1.457(2) . y C1 C16 1.532(3) . y C1 C15 1.552(3) . y C1 C2 1.562(3) . y C2 C3 1.514(3) . y C2 C9 1.515(3) . y C2 H2 0.9800 . y C3 C8 1.383(3) . y C3 C4 1.386(3) . y C4 C5 1.382(3) . y C4 H4 0.9300 . y C5 C6 1.369(3) . y C5 H5 0.9300 . y C6 C7 1.362(3) . y C6 H6 0.9300 . y C7 C8 1.390(3) . y C7 H7 0.9300 . y C8 H8 0.9300 . y C9 C10 1.387(3) . y C9 C14 1.393(3) . y C10 C11 1.384(3) . y C10 H10 0.9300 . y C11 C12 1.387(3) . y C11 H11 0.9300 . y C12 C13 1.368(3) . y C12 H12 0.9300 . y C13 C14 1.391(3) . y C13 H13 0.9300 . y C14 C15 1.461(3) . y C17 H17A 0.9600 . y C17 H17B 0.9600 . y C17 H17C 0.9600 . y 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 C16 O3 C17 116.43(17) . . y C16 C1 C15 109.62(16) . . y C16 C1 C2 112.47(15) . . y C15 C1 C2 104.79(15) . . y C16 C1 Cl1 108.82(14) . . y C15 C1 Cl1 110.56(13) . . y C2 C1 Cl1 110.55(13) . . y C3 C2 C9 118.76(17) . . y C3 C2 C1 114.95(15) . . y C9 C2 C1 103.50(16) . . y C3 C2 H2 106.2 . . y C9 C2 H2 106.2 . . y C1 C2 H2 106.2 . . y C8 C3 C4 118.4(2) . . y C8 C3 C2 123.05(19) . . y C4 C3 C2 118.5(2) . . y C5 C4 C3 121.0(2) . . y C5 C4 H4 119.5 . . y C3 C4 H4 119.5 . . y C6 C5 C4 119.8(2) . . y C6 C5 H5 120.1 . . y C4 C5 H5 120.1 . . y C7 C6 C5 120.0(2) . . y C7 C6 H6 120.0 . . y C5 C6 H6 120.0 . . y C6 C7 C8 120.7(2) . . y C6 C7 H7 119.7 . . y C8 C7 H7 119.7 . . y C3 C8 C7 120.0(2) . . y C3 C8 H8 120.0 . . y C7 C8 H8 120.0 . . y C10 C9 C14 119.2(2) . . y C10 C9 C2 128.86(19) . . y C14 C9 C2 111.73(19) . . y C11 C10 C9 118.9(2) . . y C11 C10 H10 120.6 . . y C9 C10 H10 120.6 . . y C10 C11 C12 121.3(2) . . y C10 C11 H11 119.3 . . y C12 C11 H11 119.3 . . y C13 C12 C11 120.5(2) . . y C13 C12 H12 119.8 . . y C11 C12 H12 119.8 . . y C12 C13 C14 118.5(2) . . y C12 C13 H13 120.8 . . y C14 C13 H13 120.8 . . y C13 C14 C9 121.7(2) . . y C13 C14 C15 127.8(2) . . y C9 C14 C15 110.51(19) . . y O1 C15 C14 128.9(2) . . y O1 C15 C1 124.08(19) . . y C14 C15 C1 107.02(17) . . y O2 C16 O3 125.1(2) . . y O2 C16 C1 126.5(2) . . y O3 C16 C1 108.46(18) . . y O3 C17 H17A 109.5 . . y O3 C17 H17B 109.5 . . y H17A C17 H17B 109.5 . . y O3 C17 H17C 109.5 . . y H17A C17 H17C 109.5 . . y H17B C17 H17C 109.5 . . y 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 C16 C1 C2 C3 27.4(2) . . . . y C15 C1 C2 C3 146.37(17) . . . . y Cl1 C1 C2 C3 -94.50(18) . . . . y C16 C1 C2 C9 -103.75(18) . . . . y C15 C1 C2 C9 15.26(18) . . . . y Cl1 C1 C2 C9 134.39(13) . . . . y C9 C2 C3 C8 29.7(3) . . . . y C1 C2 C3 C8 -93.6(2) . . . . y C9 C2 C3 C4 -152.26(19) . . . . y C1 C2 C3 C4 84.4(2) . . . . y C8 C3 C4 C5 0.9(3) . . . . y C2 C3 C4 C5 -177.24(19) . . . . y C3 C4 C5 C6 -1.0(4) . . . . y C4 C5 C6 C7 0.7(4) . . . . y C5 C6 C7 C8 -0.3(4) . . . . y C4 C3 C8 C7 -0.5(3) . . . . y C2 C3 C8 C7 177.5(2) . . . . y C6 C7 C8 C3 0.3(4) . . . . y C3 C2 C9 C10 45.1(3) . . . . y C1 C2 C9 C10 173.87(19) . . . . y C3 C2 C9 C14 -140.72(18) . . . . y C1 C2 C9 C14 -11.9(2) . . . . y C14 C9 C10 C11 -0.4(3) . . . . y C2 C9 C10 C11 173.45(19) . . . . y C9 C10 C11 C12 0.6(3) . . . . y C10 C11 C12 C13 -0.4(3) . . . . y C11 C12 C13 C14 0.1(3) . . . . y C12 C13 C14 C9 0.1(3) . . . . y C12 C13 C14 C15 -177.50(19) . . . . y C10 C9 C14 C13 0.1(3) . . . . y C2 C9 C14 C13 -174.79(17) . . . . y C10 C9 C14 C15 178.04(17) . . . . y C2 C9 C14 C15 3.2(2) . . . . y C13 C14 C15 O1 5.2(4) . . . . y C9 C14 C15 O1 -172.6(2) . . . . y C13 C14 C15 C1 -175.01(18) . . . . y C9 C14 C15 C1 7.2(2) . . . . y C16 C1 C15 O1 -73.4(2) . . . . y C2 C1 C15 O1 165.69(19) . . . . y Cl1 C1 C15 O1 46.6(2) . . . . y C16 C1 C15 C14 106.83(18) . . . . y C2 C1 C15 C14 -14.08(19) . . . . y Cl1 C1 C15 C14 -133.21(14) . . . . y C17 O3 C16 O2 3.0(3) . . . . y C17 O3 C16 C1 -176.58(17) . . . . y C15 C1 C16 O2 133.6(2) . . . . y C2 C1 C16 O2 -110.2(2) . . . . y Cl1 C1 C16 O2 12.6(3) . . . . y C15 C1 C16 O3 -46.8(2) . . . . y C2 C1 C16 O3 69.4(2) . . . . y Cl1 C1 C16 O3 -167.79(14) . . . . y _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.174 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.044