# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. You Huang' _publ_contact_author_email hyou@nankai.edu.cn _publ_section_title ; Bifunctional Phosphine-Catalyzed Cross-Rauhut-Currier/Michael/Aldol Condensation Triple Domino Reaction: Synthesis of Functionalized Cyclohexenes ; loop_ _publ_author_name 'You Huang' 'Peizhong Xie' 'Wenqing Lai' 'Xiangtai Meng' 'Ruyu Chen' # Attachment 'trans-3ashelxl.cif' data_shelxlb _database_code_depnum_ccdc_archive 'CCDC 769828' #TrackingRef 'trans-3ashelxl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Cl2 N O3' _chemical_formula_weight 364.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 9.823(2) _cell_length_b 11.349(2) _cell_length_c 15.262(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.43(3) _cell_angle_gamma 90.00 _cell_volume 1687.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 3.602 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.3130 _exptl_absorpt_correction_T_max 0.3571 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\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 16620 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.54 _diffrn_reflns_theta_max 72.28 _reflns_number_total 3187 _reflns_number_gt 3119 _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^)+(0.1022P)^2^+1.4636P] 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 0.0098(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3187 _refine_ls_number_parameters 281 _refine_ls_number_restraints 38 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1539 _refine_ls_wR_factor_gt 0.1533 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.134 _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 1.04623(6) 0.40881(6) 0.30395(4) 0.0287(3) Uani 1 1 d . A . Cl2 Cl 1.11978(6) 0.13316(5) 0.03083(4) 0.0228(2) Uani 1 1 d . A . O1 O 0.35621(17) 0.47345(15) 0.44280(11) 0.0212(4) Uani 1 1 d . . . C1 C 0.4269(2) 0.3862(2) 0.44760(14) 0.0168(5) Uani 1 1 d . . . H1 H 0.4154 0.3304 0.4925 0.020 Uiso 1 1 calc R . . C2 C 0.5299(2) 0.3608(2) 0.38797(14) 0.0155(5) Uani 1 1 d . A . C3 C 0.5957(2) 0.2571(2) 0.39470(14) 0.0184(5) Uani 1 1 d . . . H3 H 0.5747 0.2030 0.4385 0.022 Uiso 1 1 calc R . . C4 C 0.6983(2) 0.2233(2) 0.33781(14) 0.0179(5) Uani 1 1 d . A . C5 C 0.7435(2) 0.32228(19) 0.28097(14) 0.0155(5) Uani 1 1 d D . . H5A H 0.7952 0.3772 0.3199 0.019 Uiso 0.489(6) 1 d PR A 1 H5B H 0.8021 0.3703 0.3217 0.019 Uiso 0.511(6) 1 d PR A 2 C7 C 0.5528(2) 0.4525(2) 0.32007(15) 0.0200(5) Uani 1 1 d D . . H7A H 0.6194 0.5091 0.3450 0.024 Uiso 0.489(6) 1 d PR A 1 H7B H 0.4686 0.4931 0.3006 0.024 Uiso 0.489(6) 1 d PR A 1 H7C H 0.6065 0.5155 0.3487 0.024 Uiso 0.511(6) 1 d PR A 2 H7D H 0.4657 0.4845 0.2956 0.024 Uiso 0.511(6) 1 d PR A 2 C8 C 0.7466(3) 0.1135(2) 0.33955(17) 0.0291(6) Uani 1 1 d . . . H8A H 0.7145 0.0568 0.3778 0.035 Uiso 1 1 calc R A . H8B H 0.8132 0.0920 0.3025 0.035 Uiso 1 1 calc R . . C9 C 0.8354(2) 0.28261(19) 0.21384(14) 0.0140(4) Uani 1 1 d . A . C10 C 0.9737(2) 0.3135(2) 0.22148(13) 0.0146(5) Uani 1 1 d . . . C11 C 1.0618(2) 0.2699(2) 0.16460(13) 0.0156(5) Uani 1 1 d . A . H11 H 1.1561 0.2913 0.1719 0.019 Uiso 1 1 calc R . . C12 C 1.0089(2) 0.19506(19) 0.09757(14) 0.0144(5) Uani 1 1 d . . . C13 C 0.8707(2) 0.1653(2) 0.08481(14) 0.0163(5) Uani 1 1 d . A . H13 H 0.8347 0.1163 0.0369 0.020 Uiso 1 1 calc R . . C14 C 0.7860(2) 0.2088(2) 0.14369(15) 0.0165(5) Uani 1 1 d . . . H14 H 0.6917 0.1877 0.1359 0.020 Uiso 1 1 calc R A . O2 O 0.5643(5) 0.4789(4) 0.0911(3) 0.0370(13) Uani 0.489(6) 1 d PD A 1 O3 O 0.7365(5) 0.5469(4) 0.1910(4) 0.0245(12) Uani 0.489(6) 1 d PD A 1 N1 N 0.4154(5) 0.2430(6) 0.1661(4) 0.0215(12) Uani 0.489(6) 1 d PD A 1 C15 C 0.4988(8) 0.3035(7) 0.1966(5) 0.0143(17) Uani 0.489(6) 1 d PDU A 1 C6 C 0.6062(7) 0.3872(7) 0.2397(5) 0.0146(9) Uani 0.489(6) 1 d PD A 1 C16 C 0.6312(6) 0.4747(5) 0.1645(4) 0.0187(12) Uani 0.489(6) 1 d PD A 1 C17 C 0.7787(7) 0.6250(5) 0.1239(4) 0.0325(16) Uani 0.489(6) 1 d PD A 1 H17A H 0.8265 0.6944 0.1526 0.039 Uiso 0.489(6) 1 calc PR A 1 H17B H 0.6967 0.6531 0.0850 0.039 Uiso 0.489(6) 1 calc PR A 1 C18 C 0.8737(19) 0.561(3) 0.0690(19) 0.040(2) Uani 0.489(6) 1 d PDU A 1 H18A H 0.9536 0.5312 0.1077 0.059 Uiso 0.489(6) 1 calc PR A 1 H18B H 0.9043 0.6155 0.0257 0.059 Uiso 0.489(6) 1 calc PR A 1 H18C H 0.8246 0.4948 0.0380 0.059 Uiso 0.489(6) 1 calc PR A 1 O2' O 0.7597(5) 0.5785(4) 0.2404(3) 0.0298(11) Uani 0.511(6) 1 d PD A 2 O3' O 0.6572(4) 0.4978(3) 0.1129(2) 0.0194(11) Uani 0.511(6) 1 d PD A 2 N1' N 0.4348(6) 0.2908(6) 0.1459(4) 0.0254(12) Uani 0.511(6) 1 d PD A 2 C15' C 0.5193(7) 0.3381(6) 0.1887(5) 0.0099(14) Uani 0.511(6) 1 d PDU A 2 C6' C 0.6256(7) 0.4045(6) 0.2454(5) 0.0146(9) Uani 0.511(6) 1 d PD A 2 C16' C 0.6886(7) 0.5057(5) 0.2005(3) 0.0149(11) Uani 0.511(6) 1 d PD A 2 C17' C 0.7273(5) 0.5836(4) 0.0637(3) 0.0225(12) Uani 0.511(6) 1 d PD A 2 H17C H 0.7282 0.6611 0.0936 0.027 Uiso 0.511(6) 1 calc PR A 2 H17D H 0.6769 0.5925 0.0036 0.027 Uiso 0.511(6) 1 calc PR A 2 C18' C 0.8736(17) 0.546(3) 0.0571(19) 0.040(2) Uani 0.511(6) 1 d PD A 2 H18D H 0.9304 0.5588 0.1139 0.059 Uiso 0.511(6) 1 calc PR A 2 H18E H 0.9101 0.5916 0.0110 0.059 Uiso 0.511(6) 1 calc PR A 2 H18F H 0.8749 0.4616 0.0420 0.059 Uiso 0.511(6) 1 calc PR 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 Cl1 0.0238(4) 0.0449(4) 0.0176(3) -0.0181(2) 0.0031(2) -0.0138(2) Cl2 0.0203(3) 0.0302(4) 0.0197(3) -0.0099(2) 0.0094(2) -0.0038(2) O1 0.0173(8) 0.0244(9) 0.0225(8) -0.0016(7) 0.0047(6) 0.0023(7) C1 0.0171(11) 0.0222(11) 0.0108(10) -0.0026(8) 0.0007(8) -0.0024(9) C2 0.0167(11) 0.0194(11) 0.0100(10) -0.0026(8) 0.0006(8) -0.0015(8) C3 0.0228(11) 0.0234(12) 0.0095(10) 0.0014(8) 0.0035(8) 0.0030(9) C4 0.0201(11) 0.0235(12) 0.0097(10) 0.0012(8) 0.0003(8) 0.0041(9) C5 0.0157(10) 0.0169(11) 0.0142(10) -0.0055(8) 0.0031(8) -0.0009(8) C7 0.0260(12) 0.0139(11) 0.0224(12) 0.0007(9) 0.0118(9) 0.0034(9) C8 0.0400(16) 0.0302(14) 0.0195(12) 0.0086(10) 0.0135(11) 0.0168(11) C9 0.0160(10) 0.0147(10) 0.0114(10) -0.0012(8) 0.0017(8) 0.0007(8) C10 0.0181(11) 0.0175(11) 0.0076(9) 0.0002(8) -0.0009(8) -0.0025(8) C11 0.0128(10) 0.0228(11) 0.0109(10) 0.0014(8) 0.0005(8) -0.0029(8) C12 0.0176(11) 0.0152(10) 0.0107(9) 0.0007(8) 0.0029(8) 0.0003(8) C13 0.0179(11) 0.0175(10) 0.0130(10) -0.0051(8) 0.0000(8) -0.0017(8) C14 0.0130(10) 0.0179(11) 0.0183(11) -0.0052(8) 0.0007(8) -0.0012(8) O2 0.031(3) 0.052(3) 0.025(2) 0.0235(18) -0.0085(18) -0.010(2) O3 0.035(3) 0.019(2) 0.021(3) 0.001(2) 0.009(2) -0.0126(18) N1 0.018(2) 0.021(3) 0.024(3) -0.004(2) -0.0001(19) 0.000(2) C15 0.019(3) 0.014(3) 0.011(3) 0.008(2) 0.004(2) 0.000(2) C6 0.0173(19) 0.0101(19) 0.0181(13) 0.0036(12) 0.0083(13) -0.0013(14) C16 0.021(3) 0.019(3) 0.018(3) 0.003(2) 0.006(3) 0.006(2) C17 0.047(4) 0.020(3) 0.033(3) 0.006(2) 0.016(3) -0.010(2) C18 0.0379(17) 0.044(6) 0.040(6) 0.021(4) 0.019(2) 0.005(2) O2' 0.051(3) 0.024(2) 0.014(2) -0.0054(16) 0.0042(17) -0.0188(17) O3' 0.025(2) 0.0227(18) 0.0098(19) 0.0014(14) 0.0002(15) 0.0003(14) N1' 0.024(3) 0.029(3) 0.023(3) -0.007(2) -0.001(2) -0.003(2) C15' 0.013(2) 0.008(3) 0.009(2) 0.004(2) 0.0046(19) 0.002(2) C6' 0.0173(19) 0.0101(19) 0.0181(13) 0.0036(12) 0.0083(13) -0.0013(14) C16' 0.018(3) 0.018(3) 0.008(3) -0.003(2) 0.001(2) 0.000(2) C17' 0.030(3) 0.027(3) 0.011(2) 0.0072(19) 0.0043(19) 0.002(2) C18' 0.0379(17) 0.044(6) 0.040(6) 0.021(4) 0.019(2) 0.005(2) _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 C10 1.741(2) . ? Cl2 C12 1.733(2) . ? O1 C1 1.206(3) . ? C1 C2 1.475(3) . ? C1 H1 0.9500 . ? C2 C3 1.340(3) . ? C2 C7 1.505(3) . ? C3 C4 1.464(3) . ? C3 H3 0.9500 . ? C4 C8 1.332(4) . ? C4 C5 1.520(3) . ? C5 C9 1.519(3) . ? C5 C6' 1.531(7) . ? C5 C6 1.593(7) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C7 C6' 1.522(7) . ? C7 C6 1.580(7) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C7 H7D 0.9600 . ? C8 H8A 0.9500 . ? C8 H8B 0.9500 . ? C9 C10 1.393(3) . ? C9 C14 1.396(3) . ? C10 C11 1.394(3) . ? C11 C12 1.379(3) . ? C11 H11 0.9500 . ? C12 C13 1.388(3) . ? C13 C14 1.392(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? O2 C16 1.225(7) . ? O3 C16 1.341(6) . ? O3 C17 1.455(6) . ? N1 C15 1.122(7) . ? C15 C6 1.507(7) . ? C6 C16 1.560(8) . ? C17 C18 1.517(10) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O2' C16' 1.196(7) . ? O3' C16' 1.337(6) . ? O3' C17' 1.456(5) . ? N1' C15' 1.124(7) . ? C15' C6' 1.475(7) . ? C6' C16' 1.509(8) . ? C17' C18' 1.516(10) . ? C17' H17C 0.9900 . ? C17' H17D 0.9900 . ? C18' H18D 0.9800 . ? C18' H18E 0.9800 . ? C18' H18F 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 O1 C1 C2 123.9(2) . . ? O1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C3 C2 C1 119.1(2) . . ? C3 C2 C7 123.1(2) . . ? C1 C2 C7 117.74(19) . . ? C2 C3 C4 123.2(2) . . ? C2 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? C8 C4 C3 120.3(2) . . ? C8 C4 C5 125.0(2) . . ? C3 C4 C5 114.7(2) . . ? C9 C5 C4 114.12(18) . . ? C9 C5 C6' 115.5(3) . . ? C4 C5 C6' 112.9(3) . . ? C9 C5 C6 114.6(3) . . ? C4 C5 C6 105.9(3) . . ? C6' C5 C6 10.0(5) . . ? C9 C5 H5A 107.3 . . ? C4 C5 H5A 107.3 . . ? C6' C5 H5A 98.0 . . ? C6 C5 H5A 107.3 . . ? C9 C5 H5B 104.2 . . ? C4 C5 H5B 104.2 . . ? C6' C5 H5B 104.2 . . ? C6 C5 H5B 113.5 . . ? H5A C5 H5B 6.3 . . ? C2 C7 C6' 113.2(3) . . ? C2 C7 C6 107.7(3) . . ? C6' C7 C6 10.1(5) . . ? C2 C7 H7A 110.1 . . ? C6' C7 H7A 100.0 . . ? C6 C7 H7A 110.1 . . ? C2 C7 H7B 110.2 . . ? C6' C7 H7B 114.2 . . ? C6 C7 H7B 110.1 . . ? H7A C7 H7B 108.5 . . ? C2 C7 H7C 108.9 . . ? C6' C7 H7C 108.9 . . ? C6 C7 H7C 119.0 . . ? H7A C7 H7C 9.7 . . ? H7B C7 H7C 100.6 . . ? C2 C7 H7D 109.0 . . ? C6' C7 H7D 109.0 . . ? C6 C7 H7D 104.1 . . ? H7A C7 H7D 115.4 . . ? H7B C7 H7D 7.5 . . ? H7C C7 H7D 107.8 . . ? C4 C8 H8A 120.0 . . ? C4 C8 H8B 120.0 . . ? H8A C8 H8B 120.0 . . ? C10 C9 C14 117.0(2) . . ? C10 C9 C5 121.83(19) . . ? C14 C9 C5 121.14(19) . . ? C9 C10 C11 122.4(2) . . ? C9 C10 Cl1 121.36(17) . . ? C11 C10 Cl1 116.20(17) . . ? C12 C11 C10 118.4(2) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C13 121.4(2) . . ? C11 C12 Cl2 118.75(17) . . ? C13 C12 Cl2 119.76(17) . . ? C12 C13 C14 118.6(2) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? C13 C14 C9 122.1(2) . . ? C13 C14 H14 119.0 . . ? C9 C14 H14 119.0 . . ? C16 O3 C17 116.0(5) . . ? N1 C15 C6 177.6(9) . . ? C15 C6 C16 104.4(5) . . ? C15 C6 C7 110.5(6) . . ? C16 C6 C7 111.8(5) . . ? C15 C6 C5 112.9(6) . . ? C16 C6 C5 112.3(5) . . ? C7 C6 C5 105.0(4) . . ? O2 C16 O3 123.7(5) . . ? O2 C16 C6 125.5(5) . . ? O3 C16 C6 110.9(5) . . ? O3 C17 C18 110.5(16) . . ? O3 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? O3 C17 H17B 109.6 . . ? C18 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C16' O3' C17' 114.1(4) . . ? N1' C15' C6' 177.3(8) . . ? C15' C6' C16' 115.0(6) . . ? C15' C6' C7 104.9(5) . . ? C16' C6' C7 109.1(5) . . ? C15' C6' C5 110.0(5) . . ? C16' C6' C5 106.8(4) . . ? C7 C6' C5 111.1(5) . . ? O2' C16' O3' 126.8(6) . . ? O2' C16' C6' 122.8(5) . . ? O3' C16' C6' 110.4(6) . . ? O3' C17' C18' 111.1(15) . . ? O3' C17' H17C 109.4 . . ? C18' C17' H17C 109.4 . . ? O3' C17' H17D 109.4 . . ? C18' C17' H17D 109.4 . . ? H17C C17' H17D 108.0 . . ? C17' C18' H18D 109.5 . . ? C17' C18' H18E 109.5 . . ? H18D C18' H18E 109.5 . . ? C17' C18' H18F 109.5 . . ? H18D C18' H18F 109.5 . . ? H18E C18' H18F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -175.0(2) . . . . ? O1 C1 C2 C7 3.1(3) . . . . ? C1 C2 C3 C4 179.2(2) . . . . ? C7 C2 C3 C4 1.2(4) . . . . ? C2 C3 C4 C8 -171.0(2) . . . . ? C2 C3 C4 C5 10.2(3) . . . . ? C8 C4 C5 C9 8.8(3) . . . . ? C3 C4 C5 C9 -172.43(18) . . . . ? C8 C4 C5 C6' 143.3(4) . . . . ? C3 C4 C5 C6' -37.9(4) . . . . ? C8 C4 C5 C6 135.8(4) . . . . ? C3 C4 C5 C6 -45.4(3) . . . . ? C3 C2 C7 C6' 15.8(4) . . . . ? C1 C2 C7 C6' -162.3(3) . . . . ? C3 C2 C7 C6 24.8(4) . . . . ? C1 C2 C7 C6 -153.2(3) . . . . ? C4 C5 C9 C10 -110.9(2) . . . . ? C6' C5 C9 C10 115.8(3) . . . . ? C6 C5 C9 C10 126.8(4) . . . . ? C4 C5 C9 C14 66.2(3) . . . . ? C6' C5 C9 C14 -67.1(4) . . . . ? C6 C5 C9 C14 -56.1(4) . . . . ? C14 C9 C10 C11 -2.6(3) . . . . ? C5 C9 C10 C11 174.6(2) . . . . ? C14 C9 C10 Cl1 177.87(17) . . . . ? C5 C9 C10 Cl1 -5.0(3) . . . . ? C9 C10 C11 C12 1.1(3) . . . . ? Cl1 C10 C11 C12 -179.31(17) . . . . ? C10 C11 C12 C13 1.6(3) . . . . ? C10 C11 C12 Cl2 -176.00(16) . . . . ? C11 C12 C13 C14 -2.6(3) . . . . ? Cl2 C12 C13 C14 174.93(17) . . . . ? C12 C13 C14 C9 1.1(3) . . . . ? C10 C9 C14 C13 1.4(3) . . . . ? C5 C9 C14 C13 -175.8(2) . . . . ? N1 C15 C6 C16 -105(19) . . . . ? N1 C15 C6 C7 15(19) . . . . ? N1 C15 C6 C5 132(19) . . . . ? C2 C7 C6 C15 63.3(6) . . . . ? C6' C7 C6 C15 -172(3) . . . . ? C2 C7 C6 C16 179.1(4) . . . . ? C6' C7 C6 C16 -56(3) . . . . ? C2 C7 C6 C5 -58.8(4) . . . . ? C6' C7 C6 C5 66(3) . . . . ? C9 C5 C6 C15 76.2(6) . . . . ? C4 C5 C6 C15 -50.5(6) . . . . ? C6' C5 C6 C15 173(3) . . . . ? C9 C5 C6 C16 -41.5(6) . . . . ? C4 C5 C6 C16 -168.2(4) . . . . ? C6' C5 C6 C16 56(3) . . . . ? C9 C5 C6 C7 -163.3(3) . . . . ? C4 C5 C6 C7 70.0(4) . . . . ? C6' C5 C6 C7 -66(3) . . . . ? C17 O3 C16 O2 -6.4(8) . . . . ? C17 O3 C16 C6 174.1(5) . . . . ? C15 C6 C16 O2 7.4(8) . . . . ? C7 C6 C16 O2 -112.1(6) . . . . ? C5 C6 C16 O2 130.2(6) . . . . ? C15 C6 C16 O3 -173.0(5) . . . . ? C7 C6 C16 O3 67.5(6) . . . . ? C5 C6 C16 O3 -50.3(6) . . . . ? C16 O3 C17 C18 -82.7(12) . . . . ? N1' C15' C6' C16' -78(16) . . . . ? N1' C15' C6' C7 42(16) . . . . ? N1' C15' C6' C5 162(16) . . . . ? C2 C7 C6' C15' 76.5(5) . . . . ? C6 C7 C6' C15' 18(3) . . . . ? C2 C7 C6' C16' -159.8(4) . . . . ? C6 C7 C6' C16' 141(3) . . . . ? C2 C7 C6' C5 -42.3(5) . . . . ? C6 C7 C6' C5 -101(3) . . . . ? C9 C5 C6' C15' 72.4(6) . . . . ? C4 C5 C6' C15' -61.5(6) . . . . ? C6 C5 C6' C15' -15(3) . . . . ? C9 C5 C6' C16' -53.0(5) . . . . ? C4 C5 C6' C16' 173.1(3) . . . . ? C6 C5 C6' C16' -141(3) . . . . ? C9 C5 C6' C7 -172.0(3) . . . . ? C4 C5 C6' C7 54.2(5) . . . . ? C6 C5 C6' C7 100(3) . . . . ? C17' O3' C16' O2' 4.7(7) . . . . ? C17' O3' C16' C6' -172.9(4) . . . . ? C15' C6' C16' O2' 168.1(6) . . . . ? C7 C6' C16' O2' 50.6(7) . . . . ? C5 C6' C16' O2' -69.6(7) . . . . ? C15' C6' C16' O3' -14.2(7) . . . . ? C7 C6' C16' O3' -131.7(4) . . . . ? C5 C6' C16' O3' 108.1(5) . . . . ? C16' O3' C17' C18' 79.3(11) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 67.75 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.886 _refine_diff_density_min -0.810 _refine_diff_density_rms 0.112 # Attachment 'cis-3ashelxl.cif' data_shelxla _database_code_depnum_ccdc_archive 'CCDC 769829' #TrackingRef 'cis-3ashelxl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H15 Cl2 N O3' _chemical_formula_sum 'C18 H15 Cl2 N O3' _chemical_formula_weight 364.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9697(14) _cell_length_b 9.891(2) _cell_length_c 13.577(3) _cell_angle_alpha 91.10(3) _cell_angle_beta 103.89(3) _cell_angle_gamma 109.35(3) _cell_volume 852.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 834 _cell_measurement_theta_min 27.7 _cell_measurement_theta_max 72.1 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 3.565 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3950 _exptl_absorpt_correction_T_max 0.5993 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13359 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 72.12 _reflns_number_total 3157 _reflns_number_gt 3045 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0925P)^2^+0.2528P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0156(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3157 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _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 0.42973(7) 0.25187(4) 0.40058(3) 0.02748(18) Uani 1 1 d . . . Cl2 Cl 0.48398(8) 0.78766(4) 0.31842(4) 0.03435(19) Uani 1 1 d . . . O1 O 1.1306(2) 0.38573(14) -0.00789(10) 0.0338(3) Uani 1 1 d . . . O2 O 1.02821(18) 0.42938(12) 0.37420(9) 0.0248(3) Uani 1 1 d . . . O3 O 0.89082(18) 0.20069(12) 0.40936(8) 0.0222(3) Uani 1 1 d . . . N1 N 0.8592(2) -0.01384(15) 0.20113(10) 0.0263(3) Uani 1 1 d . . . C1 C 0.9443(3) 0.31852(18) -0.02467(13) 0.0267(4) Uani 1 1 d . . . H1 H 0.8670 0.2848 -0.0935 0.032 Uiso 1 1 calc R . . C2 C 0.8297(3) 0.28573(16) 0.05446(11) 0.0207(4) Uani 1 1 d . . . C3 C 0.6219(3) 0.20933(16) 0.02613(12) 0.0217(4) Uani 1 1 d . . . H3 H 0.5569 0.1792 -0.0444 0.026 Uiso 1 1 calc R . . C4 C 0.4916(3) 0.17044(16) 0.09697(11) 0.0199(3) Uani 1 1 d . . . C5 C 0.5952(2) 0.22555(16) 0.20925(11) 0.0182(3) Uani 1 1 d . . . H5 H 0.5248 0.1518 0.2507 0.022 Uiso 1 1 calc R . . C6 C 0.8344(2) 0.24100(16) 0.23555(11) 0.0178(3) Uani 1 1 d . . . C7 C 0.9497(2) 0.33606(16) 0.16408(11) 0.0198(3) Uani 1 1 d . . . H7A H 0.9638 0.4376 0.1799 0.024 Uiso 1 1 calc R . . H7B H 1.0929 0.3313 0.1753 0.024 Uiso 1 1 calc R . . C8 C 0.2871(3) 0.09135(19) 0.06602(13) 0.0278(4) Uani 1 1 d . . . H8A H 0.2229 0.0588 -0.0043 0.033 Uiso 1 1 calc R . . H8B H 0.2058 0.0676 0.1143 0.033 Uiso 1 1 calc R . . C9 C 0.5663(2) 0.36626(16) 0.23686(11) 0.0184(3) Uani 1 1 d . . . C10 C 0.4974(2) 0.38866(17) 0.32244(11) 0.0200(3) Uani 1 1 d . . . C11 C 0.4727(2) 0.51698(17) 0.34842(12) 0.0218(4) Uani 1 1 d . . . H11 H 0.4253 0.5290 0.4069 0.026 Uiso 1 1 calc R . . C12 C 0.5187(3) 0.62746(17) 0.28698(13) 0.0231(4) Uani 1 1 d . . . C13 C 0.5868(3) 0.61113(17) 0.20148(13) 0.0243(4) Uani 1 1 d . . . H13 H 0.6195 0.6880 0.1605 0.029 Uiso 1 1 calc R . . C14 C 0.6065(3) 0.48076(17) 0.17656(12) 0.0218(4) Uani 1 1 d . . . H14 H 0.6488 0.4685 0.1165 0.026 Uiso 1 1 calc R . . C15 C 0.9340(2) 0.30349(16) 0.34788(11) 0.0187(3) Uani 1 1 d . . . C16 C 0.9609(3) 0.2504(2) 0.51903(12) 0.0289(4) Uani 1 1 d . . . H16A H 0.9007 0.3239 0.5338 0.035 Uiso 1 1 calc R . . H16B H 1.1164 0.2939 0.5412 0.035 Uiso 1 1 calc R . . C17 C 0.8856(4) 0.1212(2) 0.57401(14) 0.0359(5) Uani 1 1 d . . . H17A H 0.7320 0.0774 0.5497 0.054 Uiso 1 1 calc R . . H17B H 0.9252 0.1509 0.6475 0.054 Uiso 1 1 calc R . . H17C H 0.9503 0.0510 0.5608 0.054 Uiso 1 1 calc R . . C18 C 0.8469(2) 0.09615(17) 0.21990(11) 0.0192(3) 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 Cl1 0.0373(3) 0.0213(3) 0.0276(3) 0.01033(16) 0.01689(18) 0.00861(18) Cl2 0.0485(3) 0.0206(3) 0.0415(3) 0.00556(18) 0.0184(2) 0.0168(2) O1 0.0381(8) 0.0326(7) 0.0349(7) 0.0145(5) 0.0186(6) 0.0107(6) O2 0.0269(6) 0.0169(6) 0.0251(6) 0.0002(4) 0.0048(5) 0.0019(5) O3 0.0280(6) 0.0194(6) 0.0150(5) 0.0045(4) 0.0025(4) 0.0048(5) N1 0.0382(8) 0.0190(7) 0.0223(7) 0.0056(5) 0.0069(6) 0.0110(6) C1 0.0390(10) 0.0209(8) 0.0232(8) 0.0082(6) 0.0113(7) 0.0115(7) C2 0.0304(8) 0.0132(7) 0.0192(7) 0.0070(6) 0.0062(6) 0.0085(6) C3 0.0311(9) 0.0139(7) 0.0179(7) 0.0042(6) 0.0016(6) 0.0081(6) C4 0.0246(8) 0.0128(7) 0.0189(7) 0.0020(5) 0.0007(6) 0.0056(6) C5 0.0194(7) 0.0140(7) 0.0180(7) 0.0036(5) 0.0038(6) 0.0020(6) C6 0.0208(7) 0.0124(7) 0.0171(7) 0.0044(5) 0.0033(6) 0.0028(6) C7 0.0225(8) 0.0141(7) 0.0203(7) 0.0050(6) 0.0058(6) 0.0029(6) C8 0.0260(8) 0.0266(9) 0.0254(8) -0.0019(7) 0.0018(6) 0.0059(7) C9 0.0175(7) 0.0141(7) 0.0193(7) 0.0026(6) 0.0014(6) 0.0022(6) C10 0.0183(7) 0.0172(7) 0.0192(7) 0.0038(6) 0.0020(6) 0.0013(6) C11 0.0197(8) 0.0201(8) 0.0222(7) 0.0013(6) 0.0046(6) 0.0033(6) C12 0.0242(8) 0.0148(7) 0.0284(8) 0.0012(6) 0.0038(6) 0.0064(6) C13 0.0287(8) 0.0178(8) 0.0268(8) 0.0086(6) 0.0073(7) 0.0081(6) C14 0.0265(8) 0.0179(8) 0.0208(7) 0.0060(6) 0.0065(6) 0.0071(6) C15 0.0185(7) 0.0172(7) 0.0181(7) 0.0029(6) 0.0028(6) 0.0045(6) C16 0.0336(9) 0.0330(9) 0.0151(7) 0.0008(7) 0.0023(6) 0.0082(8) C17 0.0570(13) 0.0408(11) 0.0234(8) 0.0140(8) 0.0154(8) 0.0303(10) C18 0.0228(8) 0.0167(8) 0.0154(7) 0.0058(5) 0.0032(6) 0.0045(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 Cl1 C10 1.7467(17) . ? Cl2 C12 1.7404(18) . ? O1 C1 1.209(2) . ? O2 C15 1.199(2) . ? O3 C15 1.3310(19) . ? O3 C16 1.4701(19) . ? N1 C18 1.148(2) . ? C1 C2 1.466(2) . ? C1 H1 0.9500 . ? C2 C3 1.346(2) . ? C2 C7 1.503(2) . ? C3 C4 1.449(2) . ? C3 H3 0.9500 . ? C4 C8 1.335(2) . ? C4 C5 1.524(2) . ? C5 C9 1.523(2) . ? C5 C6 1.572(2) . ? C5 H5 1.0000 . ? C6 C18 1.478(2) . ? C6 C15 1.537(2) . ? C6 C7 1.543(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9500 . ? C8 H8B 0.9500 . ? C9 C10 1.400(2) . ? C9 C14 1.402(2) . ? C10 C11 1.386(2) . ? C11 C12 1.387(2) . ? C11 H11 0.9500 . ? C12 C13 1.381(2) . ? C13 C14 1.385(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C16 C17 1.499(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 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 C15 O3 C16 115.42(13) . . ? O1 C1 C2 124.20(16) . . ? O1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C3 C2 C1 118.62(15) . . ? C3 C2 C7 122.63(14) . . ? C1 C2 C7 118.74(14) . . ? C2 C3 C4 123.82(14) . . ? C2 C3 H3 118.1 . . ? C4 C3 H3 118.1 . . ? C8 C4 C3 121.94(15) . . ? C8 C4 C5 120.43(15) . . ? C3 C4 C5 117.62(13) . . ? C9 C5 C4 111.53(13) . . ? C9 C5 C6 111.85(12) . . ? C4 C5 C6 109.85(13) . . ? C9 C5 H5 107.8 . . ? C4 C5 H5 107.8 . . ? C6 C5 H5 107.8 . . ? C18 C6 C15 110.33(12) . . ? C18 C6 C7 107.29(13) . . ? C15 C6 C7 111.53(12) . . ? C18 C6 C5 108.18(12) . . ? C15 C6 C5 107.86(13) . . ? C7 C6 C5 111.61(12) . . ? C2 C7 C6 110.35(12) . . ? C2 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? C2 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C4 C8 H8A 120.0 . . ? C4 C8 H8B 120.0 . . ? H8A C8 H8B 120.0 . . ? C10 C9 C14 116.30(15) . . ? C10 C9 C5 122.45(14) . . ? C14 C9 C5 121.25(14) . . ? C11 C10 C9 122.67(14) . . ? C11 C10 Cl1 116.32(12) . . ? C9 C10 Cl1 120.98(13) . . ? C10 C11 C12 118.45(15) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? C13 C12 C11 121.32(15) . . ? C13 C12 Cl2 120.16(13) . . ? C11 C12 Cl2 118.50(13) . . ? C12 C13 C14 118.86(15) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C13 C14 C9 122.35(15) . . ? C13 C14 H14 118.8 . . ? C9 C14 H14 118.8 . . ? O2 C15 O3 126.03(14) . . ? O2 C15 C6 123.20(14) . . ? O3 C15 C6 110.68(12) . . ? O3 C16 C17 107.11(14) . . ? O3 C16 H16A 110.3 . . ? C17 C16 H16A 110.3 . . ? O3 C16 H16B 110.3 . . ? C17 C16 H16B 110.3 . . ? H16A C16 H16B 108.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C18 C6 175.11(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -179.73(16) . . . . ? O1 C1 C2 C7 -1.0(3) . . . . ? C1 C2 C3 C4 -179.85(14) . . . . ? C7 C2 C3 C4 1.4(2) . . . . ? C2 C3 C4 C8 -178.24(16) . . . . ? C2 C3 C4 C5 2.9(2) . . . . ? C8 C4 C5 C9 -84.76(18) . . . . ? C3 C4 C5 C9 94.13(17) . . . . ? C8 C4 C5 C6 150.64(15) . . . . ? C3 C4 C5 C6 -30.46(18) . . . . ? C9 C5 C6 C18 172.28(12) . . . . ? C4 C5 C6 C18 -63.30(15) . . . . ? C9 C5 C6 C15 52.94(15) . . . . ? C4 C5 C6 C15 177.35(12) . . . . ? C9 C5 C6 C7 -69.91(16) . . . . ? C4 C5 C6 C7 54.50(16) . . . . ? C3 C2 C7 C6 23.0(2) . . . . ? C1 C2 C7 C6 -155.66(14) . . . . ? C18 C6 C7 C2 67.88(16) . . . . ? C15 C6 C7 C2 -171.18(13) . . . . ? C5 C6 C7 C2 -50.46(17) . . . . ? C4 C5 C9 C10 131.76(15) . . . . ? C6 C5 C9 C10 -104.77(16) . . . . ? C4 C5 C9 C14 -47.77(19) . . . . ? C6 C5 C9 C14 75.70(18) . . . . ? C14 C9 C10 C11 -1.1(2) . . . . ? C5 C9 C10 C11 179.38(13) . . . . ? C14 C9 C10 Cl1 176.94(11) . . . . ? C5 C9 C10 Cl1 -2.6(2) . . . . ? C9 C10 C11 C12 -0.1(2) . . . . ? Cl1 C10 C11 C12 -178.22(12) . . . . ? C10 C11 C12 C13 0.3(2) . . . . ? C10 C11 C12 Cl2 179.05(11) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? Cl2 C12 C13 C14 -177.95(12) . . . . ? C12 C13 C14 C9 -2.1(3) . . . . ? C10 C9 C14 C13 2.2(2) . . . . ? C5 C9 C14 C13 -178.25(14) . . . . ? C16 O3 C15 O2 2.3(2) . . . . ? C16 O3 C15 C6 -174.33(13) . . . . ? C18 C6 C15 O2 145.67(16) . . . . ? C7 C6 C15 O2 26.5(2) . . . . ? C5 C6 C15 O2 -96.36(18) . . . . ? C18 C6 C15 O3 -37.62(17) . . . . ? C7 C6 C15 O3 -156.76(13) . . . . ? C5 C6 C15 O3 80.35(15) . . . . ? C15 O3 C16 C17 176.34(15) . . . . ? C15 C6 C18 N1 -142.6(19) . . . . ? C7 C6 C18 N1 -21(2) . . . . ? C5 C6 C18 N1 99.6(19) . . . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 67.75 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.445 _refine_diff_density_min -0.627 _refine_diff_density_rms 0.076