# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Yimin Hu' _publ_contact_author_email YIMINHU@MAIL.AHNU.EDU.CN _publ_section_title ; Rapid construction of five contiguous stereocenters in a mult-cascade reaction ; loop_ _publ_author_name 'Yimin Hu' 'Qiong Hu' 'Ying Ouyang' 'Yuan Qu' 'Hao Yao' # Attachment '715801cif.txt' data_CCDC-715801 _database_code_depnum_ccdc_archive 'CCDC 715801' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Ethyl _chemical_melting_point 398K _chemical_formula_moiety 'C31 H31 N O3' _chemical_formula_sum 'C31 H31 N O3' _chemical_formula_weight 465.57 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' N N 0.0061 0.0033 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4744(12) _cell_length_b 11.3260(18) _cell_length_c 12.1119(14) _cell_angle_alpha 101.212(2) _cell_angle_beta 114.341(3) _cell_angle_gamma 98.914(1) _cell_volume 1239.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4104 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 23.37 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _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 9750 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4799 _reflns_number_gt 3754 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.05P)^2^+0.22P] 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 4799 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.2624(2) 0.80572(16) 0.20343(17) 0.0469(4) Uani 1 1 d . . . H1 H -0.1643 0.8378 0.2603 0.056 Uiso 1 1 calc R . . C2 C -0.3341(2) 0.87445(17) 0.12707(17) 0.0478(4) Uani 1 1 d . . . H2 H -0.2845 0.9529 0.1331 0.057 Uiso 1 1 calc R . . C3 C -0.47824(19) 0.82711(16) 0.04261(16) 0.0442(4) Uani 1 1 d . . . H3 H -0.5265 0.8744 -0.0072 0.053 Uiso 1 1 calc R . . C4 C -0.5516(2) 0.71098(17) 0.03094(18) 0.0485(4) Uani 1 1 d . . . H4 H -0.6488 0.6782 -0.0280 0.058 Uiso 1 1 calc R . . C5 C -0.4804(2) 0.64314(18) 0.10708(18) 0.0526(5) Uani 1 1 d . . . H5 H -0.5304 0.5641 0.0990 0.063 Uiso 1 1 calc R . . C6 C -0.3358(2) 0.68965(16) 0.19558(17) 0.0460(4) Uani 1 1 d . . . C7 C -0.2670(2) 0.61211(16) 0.27976(18) 0.0457(4) Uani 1 1 d . . . H7A H -0.2985 0.6194 0.3452 0.055 Uiso 1 1 calc R . . H7B H -0.3025 0.5253 0.2298 0.055 Uiso 1 1 calc R . . C8 C -0.01631(19) 0.73720(15) 0.46466(16) 0.0418(4) Uani 1 1 d . . . H8 H -0.0548 0.8103 0.4723 0.050 Uiso 1 1 calc R . . C9 C 0.0018(2) 0.68336(16) 0.57453(16) 0.0455(4) Uani 1 1 d . . . H9A H -0.0828 0.6820 0.5890 0.055 Uiso 1 1 calc R . . H9B H 0.0079 0.5981 0.5527 0.055 Uiso 1 1 calc R . . C10 C 0.13734(19) 0.75919(16) 0.69533(17) 0.0444(4) Uani 1 1 d . . . H10A H 0.1285 0.8429 0.7208 0.053 Uiso 1 1 calc R . . H10B H 0.1465 0.7212 0.7625 0.053 Uiso 1 1 calc R . . C11 C 0.2725(2) 0.76566(16) 0.67590(17) 0.0451(4) Uani 1 1 d . . . H11A H 0.2818 0.6819 0.6513 0.054 Uiso 1 1 calc R . . H11B H 0.3576 0.8117 0.7549 0.054 Uiso 1 1 calc R . . C12 C 0.26495(19) 0.82936(16) 0.57398(16) 0.0414(4) Uani 1 1 d . . . H12 H 0.2671 0.9164 0.6061 0.050 Uiso 1 1 calc R . . C13 C 0.12379(19) 0.77141(16) 0.45371(16) 0.0417(4) Uani 1 1 d . . . H13 H 0.1122 0.8295 0.4021 0.050 Uiso 1 1 calc R . . C14 C 0.12521(19) 0.64855(16) 0.37652(17) 0.0440(4) Uani 1 1 d . . . H14 H 0.1556 0.5960 0.4329 0.053 Uiso 1 1 calc R . . C15 C -0.03452(19) 0.59233(15) 0.28544(16) 0.0405(4) Uani 1 1 d . . . C16 C 0.23282(19) 0.66830(16) 0.32330(16) 0.0430(4) Uani 1 1 d . . . H16 H 0.1922 0.7067 0.2551 0.052 Uiso 1 1 calc R . . C17 C 0.25732(19) 0.54719(16) 0.26747(16) 0.0436(4) Uani 1 1 d . . . C18 C 0.2137(2) 0.50241(17) 0.13917(18) 0.0476(4) Uani 1 1 d . . . H18 H 0.1638 0.5452 0.0845 0.057 Uiso 1 1 calc R . . C19 C 0.2436(2) 0.39461(16) 0.09156(17) 0.0482(4) Uani 1 1 d . . . H19 H 0.2145 0.3661 0.0053 0.058 Uiso 1 1 calc R . . C20 C 0.31533(19) 0.32969(17) 0.16988(17) 0.0469(4) Uani 1 1 d . . . H20 H 0.3358 0.2577 0.1374 0.056 Uiso 1 1 calc R . . C21 C 0.3571(2) 0.37134(16) 0.29714(17) 0.0452(4) Uani 1 1 d . . . H21 H 0.4047 0.3267 0.3508 0.054 Uiso 1 1 calc R . . C22 C 0.3286(2) 0.47944(17) 0.34570(18) 0.0470(4) Uani 1 1 d . . . H22 H 0.3578 0.5071 0.4320 0.056 Uiso 1 1 calc R . . C23 C 0.37562(19) 0.76019(15) 0.42600(15) 0.0385(4) Uani 1 1 d . . . C24 C 0.39131(19) 0.83088(15) 0.54250(16) 0.0402(4) Uani 1 1 d . . . C25 C 0.52836(19) 0.90740(15) 0.63173(17) 0.0426(4) Uani 1 1 d . . . H25 H 0.5393 0.9547 0.7086 0.051 Uiso 1 1 calc R . . C26 C 0.6485(2) 0.91504(15) 0.60936(16) 0.0436(4) Uani 1 1 d . . . C27 C 0.6303(2) 0.84926(15) 0.49239(16) 0.0417(4) Uani 1 1 d . . . H27 H 0.7088 0.8561 0.4744 0.050 Uiso 1 1 calc R . . C28 C 0.4961(2) 0.77390(17) 0.40297(18) 0.0484(4) Uani 1 1 d . . . H28 H 0.4855 0.7308 0.3247 0.058 Uiso 1 1 calc R . . C29 C 0.7965(2) 0.98909(17) 0.70680(18) 0.0463(4) Uani 1 1 d . . . C30 C 0.93672(19) 1.12804(16) 0.91361(16) 0.0429(4) Uani 1 1 d . . . H30A H 0.9769 1.1949 0.8884 0.051 Uiso 1 1 calc R . . H30B H 1.0044 1.0769 0.9358 0.051 Uiso 1 1 calc R . . C31 C 0.9119(2) 1.17991(17) 1.02264(17) 0.0499(5) Uani 1 1 d . . . H31A H 0.8467 1.2319 1.0002 0.075 Uiso 1 1 calc R . . H31B H 1.0026 1.2286 1.0931 0.075 Uiso 1 1 calc R . . H31C H 0.8701 1.1129 1.0455 0.075 Uiso 1 1 calc R . . N1 N -0.10954(16) 0.64596(13) 0.33972(14) 0.0455(4) Uani 1 1 d . . . O1 O -0.08883(13) 0.51326(11) 0.18300(12) 0.0468(3) Uani 1 1 d . . . O2 O 0.90454(13) 0.99129(11) 0.69335(11) 0.0434(3) Uani 1 1 d . . . O3 O 0.79724(13) 1.05334(11) 0.81143(12) 0.0478(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 C1 0.0482(10) 0.0404(9) 0.0389(9) 0.0057(7) 0.0113(8) 0.0080(8) C2 0.0459(10) 0.0408(9) 0.0442(10) 0.0054(8) 0.0109(8) 0.0143(8) C3 0.0430(10) 0.0449(9) 0.0403(9) 0.0078(7) 0.0152(8) 0.0168(8) C4 0.0392(10) 0.0458(10) 0.0445(10) -0.0032(8) 0.0114(8) 0.0110(8) C5 0.0438(10) 0.0462(10) 0.0476(11) -0.0013(8) 0.0099(9) 0.0075(8) C6 0.0417(10) 0.0413(9) 0.0435(10) 0.0027(7) 0.0131(8) 0.0102(7) C7 0.0445(10) 0.0390(9) 0.0449(10) 0.0083(7) 0.0152(8) 0.0078(7) C8 0.0397(9) 0.0390(8) 0.0415(9) 0.0095(7) 0.0127(8) 0.0158(7) C9 0.0488(10) 0.0398(9) 0.0426(10) 0.0105(7) 0.0167(8) 0.0107(8) C10 0.0412(9) 0.0438(9) 0.0476(10) 0.0146(8) 0.0170(8) 0.0173(8) C11 0.0423(10) 0.0437(9) 0.0466(10) 0.0159(8) 0.0138(8) 0.0190(8) C12 0.0406(9) 0.0416(9) 0.0372(9) 0.0088(7) 0.0127(8) 0.0152(7) C13 0.0437(10) 0.0419(9) 0.0386(9) 0.0159(7) 0.0133(8) 0.0190(7) C14 0.0449(10) 0.0408(9) 0.0432(10) 0.0147(7) 0.0135(8) 0.0182(8) C15 0.0398(9) 0.0366(8) 0.0411(9) 0.0130(7) 0.0120(8) 0.0159(7) C16 0.0454(10) 0.0418(9) 0.0397(9) 0.0162(7) 0.0129(8) 0.0183(8) C17 0.0412(10) 0.0403(9) 0.0420(10) 0.0101(7) 0.0127(8) 0.0117(7) C18 0.0418(10) 0.0448(9) 0.0440(10) 0.0055(8) 0.0133(8) 0.0056(8) C19 0.0463(10) 0.0396(9) 0.0362(9) -0.0082(7) 0.0113(8) -0.0033(8) C20 0.0375(9) 0.0463(10) 0.0479(10) -0.0030(8) 0.0182(8) 0.0110(8) C21 0.0431(10) 0.0395(9) 0.0486(10) 0.0145(8) 0.0151(8) 0.0131(7) C22 0.0472(10) 0.0483(10) 0.0395(9) 0.0094(8) 0.0150(8) 0.0145(8) C23 0.0402(9) 0.0365(8) 0.0379(9) 0.0164(7) 0.0123(7) 0.0167(7) C24 0.0446(10) 0.0364(8) 0.0387(9) 0.0148(7) 0.0147(8) 0.0157(7) C25 0.0438(10) 0.0376(8) 0.0406(9) 0.0103(7) 0.0131(8) 0.0145(7) C26 0.0480(10) 0.0366(8) 0.0415(9) 0.0147(7) 0.0146(8) 0.0105(7) C27 0.0430(9) 0.0399(8) 0.0418(9) 0.0177(7) 0.0153(8) 0.0138(7) C28 0.0461(10) 0.0482(10) 0.0469(10) 0.0127(8) 0.0170(9) 0.0149(8) C29 0.0422(10) 0.0440(9) 0.0472(10) 0.0136(8) 0.0144(8) 0.0137(8) C30 0.0398(9) 0.0449(9) 0.0423(9) 0.0145(8) 0.0178(8) 0.0067(7) C31 0.0484(11) 0.0457(10) 0.0377(9) -0.0028(7) 0.0131(8) 0.0020(8) N1 0.0431(8) 0.0417(8) 0.0427(8) 0.0068(6) 0.0125(7) 0.0141(6) O1 0.0435(7) 0.0437(6) 0.0454(7) 0.0114(6) 0.0126(6) 0.0144(5) O2 0.0417(7) 0.0415(6) 0.0442(7) 0.0191(5) 0.0141(6) 0.0105(5) O3 0.0411(7) 0.0399(6) 0.0479(7) 0.0033(5) 0.0123(6) 0.0062(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.381(3) . ? C1 C2 1.384(2) . ? C1 H1 0.9300 . ? C2 C3 1.369(2) . ? C2 H2 0.9300 . ? C3 C4 1.366(3) . ? C3 H3 0.9300 . ? C4 C5 1.372(3) . ? C4 H4 0.9300 . ? C5 C6 1.384(3) . ? C5 H5 0.9300 . ? C6 C7 1.506(2) . ? C7 N1 1.451(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.474(2) . ? C8 C9 1.524(2) . ? C8 C13 1.525(3) . ? C8 H8 0.9800 . ? C9 C10 1.522(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.521(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.528(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.514(2) . ? C12 C24 1.520(3) . ? C12 H12 0.9800 . ? C13 C14 1.524(2) . ? C13 H13 0.9800 . ? C14 C15 1.516(2) . ? C14 C16 1.521(3) . ? C14 H14 0.9800 . ? C15 O1 1.222(2) . ? C15 N1 1.355(2) . ? C16 C17 1.515(2) . ? C16 C23 1.532(2) . ? C16 H16 0.9800 . ? C17 C18 1.385(3) . ? C17 C22 1.386(2) . ? C18 C19 1.384(3) . ? C18 H18 0.9300 . ? C19 C20 1.364(3) . ? C19 H19 0.9300 . ? C20 C21 1.374(3) . ? C20 H20 0.9300 . ? C21 C22 1.383(2) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C28 1.393(3) . ? C23 C24 1.410(2) . ? C24 C25 1.397(2) . ? C25 C26 1.385(3) . ? C25 H25 0.9300 . ? C26 C27 1.386(2) . ? C26 C29 1.484(3) . ? C27 C28 1.375(3) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 O2 1.206(2) . ? C29 O3 1.329(2) . ? C30 O3 1.450(2) . ? C30 C31 1.479(3) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.24(17) . . ? C6 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C3 C2 C1 120.06(17) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 120.52(17) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 119.33(17) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 121.54(18) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C1 C6 C5 118.28(18) . . ? C1 C6 C7 123.28(16) . . ? C5 C6 C7 118.43(17) . . ? N1 C7 C6 114.70(15) . . ? N1 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? N1 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? N1 C8 C9 113.31(14) . . ? N1 C8 C13 99.99(14) . . ? C9 C8 C13 113.27(14) . . ? N1 C8 H8 110.0 . . ? C9 C8 H8 110.0 . . ? C13 C8 H8 110.0 . . ? C10 C9 C8 111.76(15) . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? C11 C10 C9 110.92(16) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C12 111.13(14) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C24 109.18(14) . . ? C13 C12 C11 111.45(15) . . ? C24 C12 C11 114.15(14) . . ? C13 C12 H12 107.2 . . ? C24 C12 H12 107.2 . . ? C11 C12 H12 107.2 . . ? C12 C13 C14 111.94(14) . . ? C12 C13 C8 118.45(15) . . ? C14 C13 C8 103.00(14) . . ? C12 C13 H13 107.6 . . ? C14 C13 H13 107.6 . . ? C8 C13 H13 107.6 . . ? C15 C14 C16 118.84(15) . . ? C15 C14 C13 102.03(14) . . ? C16 C14 C13 111.65(15) . . ? C15 C14 H14 107.9 . . ? C16 C14 H14 107.9 . . ? C13 C14 H14 107.9 . . ? O1 C15 N1 125.20(16) . . ? O1 C15 C14 128.10(16) . . ? N1 C15 C14 106.70(14) . . ? C17 C16 C14 112.69(15) . . ? C17 C16 C23 111.59(14) . . ? C14 C16 C23 109.53(15) . . ? C17 C16 H16 107.6 . . ? C14 C16 H16 107.6 . . ? C23 C16 H16 107.6 . . ? C18 C17 C22 118.01(16) . . ? C18 C17 C16 121.88(15) . . ? C22 C17 C16 120.08(15) . . ? C19 C18 C17 120.65(18) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 120.67(17) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 119.55(16) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C20 C21 C22 120.18(17) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C17 120.92(17) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? C28 C23 C24 118.48(16) . . ? C28 C23 C16 118.13(16) . . ? C24 C23 C16 123.38(16) . . ? C25 C24 C23 118.52(17) . . ? C25 C24 C12 118.66(16) . . ? C23 C24 C12 122.81(16) . . ? C26 C25 C24 122.06(17) . . ? C26 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? C25 C26 C27 118.81(17) . . ? C25 C26 C29 122.47(17) . . ? C27 C26 C29 118.71(18) . . ? C28 C27 C26 120.00(18) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C23 122.00(18) . . ? C27 C28 H28 119.0 . . ? C23 C28 H28 119.0 . . ? O2 C29 O3 123.33(17) . . ? O2 C29 C26 124.15(18) . . ? O3 C29 C26 112.51(17) . . ? O3 C30 C31 107.13(14) . . ? O3 C30 H30A 110.3 . . ? C31 C30 H30A 110.3 . . ? O3 C30 H30B 110.3 . . ? C31 C30 H30B 110.3 . . ? H30A C30 H30B 108.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C15 N1 C7 121.98(15) . . ? C15 N1 C8 113.73(14) . . ? C7 N1 C8 124.27(15) . . ? C29 O3 C30 117.16(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.5(3) . . . . ? C1 C2 C3 C4 -1.4(3) . . . . ? C2 C3 C4 C5 1.6(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C2 C1 C6 C5 2.1(3) . . . . ? C2 C1 C6 C7 -176.98(18) . . . . ? C4 C5 C6 C1 -1.9(3) . . . . ? C4 C5 C6 C7 177.25(18) . . . . ? C1 C6 C7 N1 -19.7(3) . . . . ? C5 C6 C7 N1 161.21(17) . . . . ? N1 C8 C9 C10 158.57(15) . . . . ? C13 C8 C9 C10 45.6(2) . . . . ? C8 C9 C10 C11 -57.86(19) . . . . ? C9 C10 C11 C12 61.23(18) . . . . ? C10 C11 C12 C13 -51.52(19) . . . . ? C10 C11 C12 C24 -175.78(14) . . . . ? C24 C12 C13 C14 48.89(19) . . . . ? C11 C12 C13 C14 -78.13(19) . . . . ? C24 C12 C13 C8 168.50(14) . . . . ? C11 C12 C13 C8 41.5(2) . . . . ? N1 C8 C13 C12 -159.71(14) . . . . ? C9 C8 C13 C12 -38.8(2) . . . . ? N1 C8 C13 C14 -35.57(15) . . . . ? C9 C8 C13 C14 85.31(16) . . . . ? C12 C13 C14 C15 164.57(15) . . . . ? C8 C13 C14 C15 36.25(16) . . . . ? C12 C13 C14 C16 -67.46(19) . . . . ? C8 C13 C14 C16 164.21(14) . . . . ? C16 C14 C15 O1 34.6(2) . . . . ? C13 C14 C15 O1 157.84(17) . . . . ? C16 C14 C15 N1 -145.98(15) . . . . ? C13 C14 C15 N1 -22.75(17) . . . . ? C15 C14 C16 C17 -72.45(18) . . . . ? C13 C14 C16 C17 169.22(13) . . . . ? C15 C14 C16 C23 162.70(13) . . . . ? C13 C14 C16 C23 44.37(17) . . . . ? C14 C16 C17 C18 113.33(19) . . . . ? C23 C16 C17 C18 -122.95(18) . . . . ? C14 C16 C17 C22 -68.4(2) . . . . ? C23 C16 C17 C22 55.3(2) . . . . ? C22 C17 C18 C19 -1.4(3) . . . . ? C16 C17 C18 C19 176.91(17) . . . . ? C17 C18 C19 C20 0.7(3) . . . . ? C18 C19 C20 C21 0.6(3) . . . . ? C19 C20 C21 C22 -1.0(3) . . . . ? C20 C21 C22 C17 0.3(3) . . . . ? C18 C17 C22 C21 0.9(3) . . . . ? C16 C17 C22 C21 -177.41(17) . . . . ? C17 C16 C23 C28 43.5(2) . . . . ? C14 C16 C23 C28 169.02(14) . . . . ? C17 C16 C23 C24 -136.16(16) . . . . ? C14 C16 C23 C24 -10.7(2) . . . . ? C28 C23 C24 C25 -2.7(2) . . . . ? C16 C23 C24 C25 176.97(14) . . . . ? C28 C23 C24 C12 175.99(15) . . . . ? C16 C23 C24 C12 -4.3(2) . . . . ? C13 C12 C24 C25 163.96(14) . . . . ? C11 C12 C24 C25 -70.57(19) . . . . ? C13 C12 C24 C23 -14.7(2) . . . . ? C11 C12 C24 C23 110.72(17) . . . . ? C23 C24 C25 C26 -0.4(2) . . . . ? C12 C24 C25 C26 -179.18(15) . . . . ? C24 C25 C26 C27 3.2(2) . . . . ? C24 C25 C26 C29 -175.60(15) . . . . ? C25 C26 C27 C28 -2.8(2) . . . . ? C29 C26 C27 C28 176.07(15) . . . . ? C26 C27 C28 C23 -0.4(3) . . . . ? C24 C23 C28 C27 3.2(2) . . . . ? C16 C23 C28 C27 -176.52(15) . . . . ? C25 C26 C29 O2 175.00(17) . . . . ? C27 C26 C29 O2 -3.8(3) . . . . ? C25 C26 C29 O3 -5.0(2) . . . . ? C27 C26 C29 O3 176.19(14) . . . . ? O1 C15 N1 C7 0.8(3) . . . . ? C14 C15 N1 C7 -178.62(15) . . . . ? O1 C15 N1 C8 179.11(16) . . . . ? C14 C15 N1 C8 -0.32(19) . . . . ? C6 C7 N1 C15 -90.9(2) . . . . ? C6 C7 N1 C8 91.0(2) . . . . ? C9 C8 N1 C15 -97.78(18) . . . . ? C13 C8 N1 C15 23.06(18) . . . . ? C9 C8 N1 C7 80.5(2) . . . . ? C13 C8 N1 C7 -158.68(15) . . . . ? O2 C29 O3 C30 -0.7(2) . . . . ? C26 C29 O3 C30 179.33(13) . . . . ? C31 C30 O3 C29 -174.51(15) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.309 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.034 ##################END # Attachment '715802cif.txt' data_CCDC-715802 _database_code_depnum_ccdc_archive 'CCDC 715802' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 4-Benzyl-9-chloro-6-(4-chlorophenyl)-1,2,3,3a,4,5a,6,10b- octahydronaphtho(3,2,1- ; _chemical_melting_point 435K _chemical_formula_moiety 'C28 H25 Cl2 N O' _chemical_formula_sum 'C28 H25 Cl2 N O' _chemical_formula_weight 462.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.0332(12) _cell_length_b 11.057(2) _cell_length_c 11.4123(18) _cell_angle_alpha 64.521(2) _cell_angle_beta 67.143(3) _cell_angle_gamma 70.442(2) _cell_volume 1134.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3927 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 25.49 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.308 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_T_max 0.943 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _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 8252 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.27 _reflns_number_total 4126 _reflns_number_gt 3146 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.05P)^2^+0.88P] 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 4126 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1206 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4059(3) 0.8143(3) 0.1296(3) 0.0415(7) Uani 1 1 d . . . H1 H 0.4209 0.7387 0.1060 0.050 Uiso 1 1 calc R . . C2 C 0.2774(3) 0.8966(3) 0.1519(3) 0.0390(7) Uani 1 1 d . . . H2 H 0.2079 0.8768 0.1407 0.047 Uiso 1 1 calc R . . C3 C 0.2539(3) 1.0041(3) 0.1894(3) 0.0415(7) Uani 1 1 d . . . H3 H 0.1675 1.0566 0.2061 0.050 Uiso 1 1 calc R . . C4 C 0.3531(3) 1.0367(3) 0.2031(3) 0.0436(7) Uani 1 1 d . . . H4 H 0.3362 1.1120 0.2278 0.052 Uiso 1 1 calc R . . C5 C 0.4819(3) 0.9563(3) 0.1798(3) 0.0402(7) Uani 1 1 d . . . H5 H 0.5501 0.9792 0.1900 0.048 Uiso 1 1 calc R . . C6 C 0.5117(3) 0.8453(3) 0.1426(3) 0.0434(7) Uani 1 1 d . . . C7 C 0.6456(3) 0.7614(3) 0.1162(3) 0.0397(7) Uani 1 1 d . . . H7A H 0.6415 0.6729 0.1214 0.048 Uiso 1 1 calc R . . H7B H 0.7011 0.8058 0.0269 0.048 Uiso 1 1 calc R . . C8 C 0.8067(3) 0.8015(3) 0.1879(3) 0.0398(7) Uani 1 1 d . . . C9 C 0.8357(3) 0.7621(3) 0.3198(3) 0.0337(6) Uani 1 1 d . . . H9 H 0.8988 0.6738 0.3341 0.040 Uiso 1 1 calc R . . C10 C 0.7031(3) 0.7395(3) 0.4236(3) 0.0357(6) Uani 1 1 d . . . H10 H 0.6473 0.8289 0.4263 0.043 Uiso 1 1 calc R . . C11 C 0.6431(3) 0.6834(3) 0.3620(3) 0.0435(7) Uani 1 1 d . . . H11 H 0.5449 0.7107 0.3879 0.052 Uiso 1 1 calc R . . C12 C 0.6864(3) 0.5301(3) 0.3972(3) 0.0417(7) Uani 1 1 d . . . H12A H 0.6306 0.4981 0.3731 0.050 Uiso 1 1 calc R . . H12B H 0.7785 0.5084 0.3441 0.050 Uiso 1 1 calc R . . C13 C 0.6762(3) 0.4563(3) 0.5454(3) 0.0436(8) Uani 1 1 d . . . H13A H 0.5835 0.4745 0.5987 0.052 Uiso 1 1 calc R . . H13B H 0.7042 0.3585 0.5634 0.052 Uiso 1 1 calc R . . C14 C 0.7626(3) 0.5016(3) 0.5864(3) 0.0462(8) Uani 1 1 d . . . H14A H 0.8554 0.4802 0.5347 0.055 Uiso 1 1 calc R . . H14B H 0.7561 0.4504 0.6815 0.055 Uiso 1 1 calc R . . C15 C 0.7242(3) 0.6535(3) 0.5646(3) 0.0445(7) Uani 1 1 d . . . H15 H 0.6359 0.6670 0.6299 0.053 Uiso 1 1 calc R . . C16 C 0.8107(3) 0.7108(3) 0.5900(3) 0.0390(7) Uani 1 1 d . . . C17 C 0.8256(3) 0.6639(4) 0.7179(3) 0.0525(9) Uani 1 1 d . . . H17 H 0.7759 0.6003 0.7875 0.063 Uiso 1 1 calc R . . C18 C 0.9108(3) 0.7072(3) 0.7478(3) 0.0440(7) Uani 1 1 d . . . C19 C 0.9826(3) 0.8022(3) 0.6477(3) 0.0391(7) Uani 1 1 d . . . H19 H 1.0379 0.8345 0.6669 0.047 Uiso 1 1 calc R . . C20 C 0.9728(3) 0.8492(3) 0.5208(3) 0.0495(8) Uani 1 1 d . . . H20 H 1.0227 0.9137 0.4533 0.059 Uiso 1 1 calc R . . C21 C 0.8924(3) 0.8055(3) 0.4878(3) 0.0443(7) Uani 1 1 d . . . C22 C 0.8916(3) 0.8601(3) 0.3382(3) 0.0389(7) Uani 1 1 d . . . H22 H 0.9853 0.8559 0.2820 0.047 Uiso 1 1 calc R . . C23 C 0.8183(3) 1.0082(3) 0.2911(3) 0.0445(7) Uani 1 1 d . . . C24 C 0.8664(3) 1.0909(3) 0.1566(3) 0.0402(7) Uani 1 1 d . . . H24 H 0.9456 1.0561 0.1014 0.048 Uiso 1 1 calc R . . C25 C 0.8001(3) 1.2215(3) 0.1043(3) 0.0425(7) Uani 1 1 d . . . H25 H 0.8339 1.2742 0.0144 0.051 Uiso 1 1 calc R . . C26 C 0.6827(3) 1.2749(3) 0.1853(3) 0.0463(8) Uani 1 1 d . . . C27 C 0.6417(3) 1.1933(3) 0.3207(3) 0.0425(7) Uani 1 1 d . . . H27 H 0.5661 1.2298 0.3781 0.051 Uiso 1 1 calc R . . C28 C 0.7058(3) 1.0645(3) 0.3728(3) 0.0440(7) Uani 1 1 d . . . H28 H 0.6739 1.0138 0.4638 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.92190(8) 0.64720(9) 0.90982(9) 0.0549(2) Uani 1 1 d . . . Cl2 Cl 0.59571(8) 1.43880(8) 0.11738(8) 0.0518(2) Uani 1 1 d . . . N1 N 0.6990(2) 0.7462(3) 0.2194(2) 0.0405(6) Uani 1 1 d . . . O1 O 0.8756(2) 0.8558(2) 0.0740(2) 0.0433(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0510(18) 0.0368(16) 0.0384(16) -0.0205(13) -0.0128(14) -0.0010(13) C2 0.0249(14) 0.0415(17) 0.0482(17) -0.0008(14) -0.0170(12) -0.0157(12) C3 0.0271(14) 0.0410(17) 0.0316(15) -0.0011(13) -0.0052(11) 0.0036(12) C4 0.0531(19) 0.0334(15) 0.0392(16) -0.0204(13) -0.0100(14) 0.0041(13) C5 0.0255(14) 0.0449(17) 0.0468(17) -0.0020(14) -0.0166(12) -0.0145(12) C6 0.0328(15) 0.0366(16) 0.0428(17) 0.0024(13) -0.0132(13) -0.0042(13) C7 0.0378(16) 0.0331(15) 0.0399(16) -0.0087(13) -0.0061(12) -0.0087(12) C8 0.0335(15) 0.0432(17) 0.0320(15) -0.0087(13) -0.0048(12) -0.0060(13) C9 0.0367(15) 0.0297(14) 0.0298(14) -0.0086(11) -0.0105(11) -0.0020(11) C10 0.0392(16) 0.0309(14) 0.0381(15) -0.0144(12) -0.0088(12) -0.0078(12) C11 0.0427(17) 0.0475(18) 0.0420(17) -0.0159(14) -0.0133(14) -0.0089(14) C12 0.0324(15) 0.0520(18) 0.0340(15) -0.0133(14) -0.0067(12) -0.0059(13) C13 0.0310(15) 0.0325(15) 0.0466(18) 0.0086(13) -0.0116(13) -0.0111(12) C14 0.0461(18) 0.0488(19) 0.0452(18) -0.0264(15) -0.0145(14) 0.0039(14) C15 0.0409(17) 0.0489(18) 0.0403(17) -0.0226(15) -0.0070(13) -0.0008(14) C16 0.0376(15) 0.0361(16) 0.0426(17) -0.0203(13) -0.0102(13) 0.0010(12) C17 0.0471(19) 0.0509(19) 0.0466(19) 0.0029(15) -0.0132(15) -0.0213(16) C18 0.0404(17) 0.0461(18) 0.0486(18) -0.0230(15) -0.0130(14) -0.0032(14) C19 0.0377(16) 0.0289(14) 0.0523(18) -0.0179(13) -0.0154(13) -0.0005(12) C20 0.0461(18) 0.0477(18) 0.0439(18) -0.0007(15) -0.0102(14) -0.0202(15) C21 0.0480(18) 0.0444(17) 0.0423(17) -0.0211(14) -0.0141(14) -0.0019(14) C22 0.0337(15) 0.0385(16) 0.0372(15) -0.0187(13) -0.0018(12) -0.0010(12) C23 0.0360(16) 0.0328(15) 0.0496(18) -0.0064(14) -0.0062(13) -0.0066(13) C24 0.0409(16) 0.0457(17) 0.0380(16) -0.0205(14) -0.0153(13) -0.0008(13) C25 0.0398(16) 0.0387(16) 0.0320(16) -0.0012(13) -0.0096(13) -0.0034(13) C26 0.0320(15) 0.0318(15) 0.0416(17) 0.0063(13) -0.0041(13) 0.0001(12) C27 0.0530(19) 0.0410(17) 0.0301(15) -0.0165(13) -0.0089(13) -0.0034(14) C28 0.0391(16) 0.0467(18) 0.0269(14) 0.0018(13) -0.0026(12) -0.0132(14) Cl1 0.0484(5) 0.0487(5) 0.0476(5) 0.0011(4) -0.0106(4) -0.0136(4) Cl2 0.0372(4) 0.0357(4) 0.0497(5) 0.0004(3) -0.0107(3) 0.0091(3) N1 0.0301(12) 0.0468(15) 0.0372(13) -0.0103(11) -0.0064(10) -0.0084(11) O1 0.0382(11) 0.0371(11) 0.0413(12) -0.0120(9) 0.0073(9) -0.0159(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.396(4) . ? C1 C2 1.399(4) . ? C1 H1 0.9300 . ? C2 C3 1.345(4) . ? C2 H2 0.9300 . ? C3 C4 1.341(5) . ? C3 H3 0.9300 . ? C4 C5 1.395(4) . ? C4 H4 0.9300 . ? C5 C6 1.365(5) . ? C5 H5 0.9300 . ? C6 C7 1.452(4) . ? C7 N1 1.437(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O1 1.222(3) . ? C8 N1 1.372(4) . ? C8 C9 1.508(4) . ? C9 C10 1.500(4) . ? C9 C22 1.530(4) . ? C9 H9 0.9800 . ? C10 C11 1.526(4) . ? C10 C15 1.541(4) . ? C10 H10 0.9800 . ? C11 N1 1.431(4) . ? C11 C12 1.512(4) . ? C11 H11 0.9800 . ? C12 C13 1.505(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.499(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.520(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.474(4) . ? C15 H15 0.9800 . ? C16 C17 1.380(4) . ? C16 C21 1.426(5) . ? C17 C18 1.386(5) . ? C17 H17 0.9300 . ? C18 C19 1.363(4) . ? C18 Cl1 1.715(3) . ? C19 C20 1.347(4) . ? C19 H19 0.9300 . ? C20 C21 1.366(5) . ? C20 H20 0.9300 . ? C21 C22 1.550(4) . ? C22 C23 1.523(4) . ? C22 H22 0.9800 . ? C23 C28 1.371(4) . ? C23 C24 1.400(4) . ? C24 C25 1.366(4) . ? C24 H24 0.9300 . ? C25 C26 1.383(4) . ? C25 H25 0.9300 . ? C26 C27 1.392(4) . ? C26 Cl2 1.735(3) . ? C27 C28 1.343(4) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? 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 C6 C1 C2 120.2(3) . . ? C6 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 121.0(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.1(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 122.6(3) . . ? C6 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C5 C6 C1 116.7(3) . . ? C5 C6 C7 123.3(3) . . ? C1 C6 C7 120.0(3) . . ? N1 C7 C6 105.7(3) . . ? N1 C7 H7A 110.6 . . ? C6 C7 H7A 110.6 . . ? N1 C7 H7B 110.6 . . ? C6 C7 H7B 110.6 . . ? H7A C7 H7B 108.7 . . ? O1 C8 N1 126.2(3) . . ? O1 C8 C9 126.9(3) . . ? N1 C8 C9 106.2(2) . . ? C10 C9 C8 103.3(2) . . ? C10 C9 C22 110.7(2) . . ? C8 C9 C22 118.9(2) . . ? C10 C9 H9 107.8 . . ? C8 C9 H9 107.8 . . ? C22 C9 H9 107.8 . . ? C9 C10 C11 102.7(2) . . ? C9 C10 C15 109.8(2) . . ? C11 C10 C15 119.3(3) . . ? C9 C10 H10 108.1 . . ? C11 C10 H10 108.1 . . ? C15 C10 H10 108.1 . . ? N1 C11 C12 108.1(2) . . ? N1 C11 C10 103.2(2) . . ? C12 C11 C10 113.0(3) . . ? N1 C11 H11 110.7 . . ? C12 C11 H11 110.7 . . ? C10 C11 H11 110.7 . . ? C13 C12 C11 112.3(3) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 110.8(3) . . ? C14 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C13 C14 C15 113.3(3) . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 117.5(3) . . ? C16 C15 C10 109.9(3) . . ? C14 C15 C10 111.4(2) . . ? C16 C15 H15 105.7 . . ? C14 C15 H15 105.7 . . ? C10 C15 H15 105.7 . . ? C17 C16 C21 115.3(3) . . ? C17 C16 C15 119.8(3) . . ? C21 C16 C15 124.6(3) . . ? C16 C17 C18 123.2(3) . . ? C16 C17 H17 118.4 . . ? C18 C17 H17 118.4 . . ? C19 C18 C17 119.3(3) . . ? C19 C18 Cl1 120.0(3) . . ? C17 C18 Cl1 120.7(3) . . ? C20 C19 C18 119.6(3) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 122.3(3) . . ? C19 C20 H20 118.8 . . ? C21 C20 H20 118.8 . . ? C20 C21 C16 120.3(3) . . ? C20 C21 C22 119.1(3) . . ? C16 C21 C22 120.7(3) . . ? C23 C22 C9 113.0(3) . . ? C23 C22 C21 113.5(2) . . ? C9 C22 C21 108.2(2) . . ? C23 C22 H22 107.3 . . ? C9 C22 H22 107.3 . . ? C21 C22 H22 107.3 . . ? C28 C23 C24 118.0(3) . . ? C28 C23 C22 123.5(3) . . ? C24 C23 C22 118.5(3) . . ? C25 C24 C23 121.8(3) . . ? C25 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? C24 C25 C26 119.8(3) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C25 C26 C27 117.1(3) . . ? C25 C26 Cl2 119.8(2) . . ? C27 C26 Cl2 123.1(2) . . ? C28 C27 C26 123.4(3) . . ? C28 C27 H27 118.3 . . ? C26 C27 H27 118.3 . . ? C27 C28 C23 119.8(3) . . ? C27 C28 H28 120.1 . . ? C23 C28 H28 120.1 . . ? C8 N1 C11 113.2(2) . . ? C8 N1 C7 121.4(2) . . ? C11 N1 C7 125.3(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.7(4) . . . . ? C1 C2 C3 C4 1.6(4) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C3 C4 C5 C6 0.4(5) . . . . ? C4 C5 C6 C1 -0.5(4) . . . . ? C4 C5 C6 C7 179.2(3) . . . . ? C2 C1 C6 C5 1.1(4) . . . . ? C2 C1 C6 C7 -178.5(3) . . . . ? C5 C6 C7 N1 41.1(4) . . . . ? C1 C6 C7 N1 -139.3(3) . . . . ? O1 C8 C9 C10 164.1(3) . . . . ? N1 C8 C9 C10 -24.7(3) . . . . ? O1 C8 C9 C22 41.1(4) . . . . ? N1 C8 C9 C22 -147.8(2) . . . . ? C8 C9 C10 C11 33.2(3) . . . . ? C22 C9 C10 C11 161.5(2) . . . . ? C8 C9 C10 C15 161.1(2) . . . . ? C22 C9 C10 C15 -70.6(3) . . . . ? C9 C10 C11 N1 -30.0(3) . . . . ? C15 C10 C11 N1 -151.7(2) . . . . ? C9 C10 C11 C12 86.6(3) . . . . ? C15 C10 C11 C12 -35.1(4) . . . . ? N1 C11 C12 C13 159.8(2) . . . . ? C10 C11 C12 C13 46.2(3) . . . . ? C11 C12 C13 C14 -59.6(3) . . . . ? C12 C13 C14 C15 60.4(3) . . . . ? C13 C14 C15 C16 -174.5(3) . . . . ? C13 C14 C15 C10 -46.4(4) . . . . ? C9 C10 C15 C16 48.7(3) . . . . ? C11 C10 C15 C16 166.8(3) . . . . ? C9 C10 C15 C14 -83.4(3) . . . . ? C11 C10 C15 C14 34.7(4) . . . . ? C14 C15 C16 C17 -61.7(4) . . . . ? C10 C15 C16 C17 169.6(3) . . . . ? C14 C15 C16 C21 112.6(3) . . . . ? C10 C15 C16 C21 -16.2(4) . . . . ? C21 C16 C17 C18 1.5(5) . . . . ? C15 C16 C17 C18 176.3(3) . . . . ? C16 C17 C18 C19 1.1(5) . . . . ? C16 C17 C18 Cl1 178.7(3) . . . . ? C17 C18 C19 C20 -2.1(5) . . . . ? Cl1 C18 C19 C20 -179.7(2) . . . . ? C18 C19 C20 C21 0.3(5) . . . . ? C19 C20 C21 C16 2.5(5) . . . . ? C19 C20 C21 C22 -177.4(3) . . . . ? C17 C16 C21 C20 -3.3(4) . . . . ? C15 C16 C21 C20 -177.7(3) . . . . ? C17 C16 C21 C22 176.6(3) . . . . ? C15 C16 C21 C22 2.1(4) . . . . ? C10 C9 C22 C23 -73.9(3) . . . . ? C8 C9 C22 C23 45.4(3) . . . . ? C10 C9 C22 C21 52.6(3) . . . . ? C8 C9 C22 C21 171.9(2) . . . . ? C20 C21 C22 C23 -73.3(4) . . . . ? C16 C21 C22 C23 106.9(3) . . . . ? C20 C21 C22 C9 160.5(3) . . . . ? C16 C21 C22 C9 -19.4(4) . . . . ? C9 C22 C23 C28 87.9(4) . . . . ? C21 C22 C23 C28 -35.7(5) . . . . ? C9 C22 C23 C24 -90.7(3) . . . . ? C21 C22 C23 C24 145.7(3) . . . . ? C28 C23 C24 C25 -3.8(5) . . . . ? C22 C23 C24 C25 174.9(3) . . . . ? C23 C24 C25 C26 0.3(5) . . . . ? C24 C25 C26 C27 3.4(5) . . . . ? C24 C25 C26 Cl2 -178.0(3) . . . . ? C25 C26 C27 C28 -4.0(5) . . . . ? Cl2 C26 C27 C28 177.4(3) . . . . ? C26 C27 C28 C23 0.6(5) . . . . ? C24 C23 C28 C27 3.3(5) . . . . ? C22 C23 C28 C27 -175.3(3) . . . . ? O1 C8 N1 C11 176.8(3) . . . . ? C9 C8 N1 C11 5.6(3) . . . . ? O1 C8 N1 C7 -7.4(5) . . . . ? C9 C8 N1 C7 -178.7(2) . . . . ? C12 C11 N1 C8 -104.4(3) . . . . ? C10 C11 N1 C8 15.6(3) . . . . ? C12 C11 N1 C7 80.1(3) . . . . ? C10 C11 N1 C7 -160.0(3) . . . . ? C6 C7 N1 C8 -114.1(3) . . . . ? C6 C7 N1 C11 61.1(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.27 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.437 _refine_diff_density_min -0.540 _refine_diff_density_rms 0.047 ##################END # Attachment '715803cif.txt' data_CCDC-715803 _database_code_depnum_ccdc_archive 'CCDC 715803' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 4-Benzyl-9-chloro-6-phenyl-1,2,3,3a,4,5a,6,10b- octahydronaphtho(3,2,1-cd)indol-5 ; _chemical_melting_point 427K _chemical_formula_moiety 'C28 H26 Cl N O' _chemical_formula_sum 'C28 H26 Cl N O' _chemical_formula_weight 427.95 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' N N 0.0061 0.0033 '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 11.383(2) _cell_length_b 9.3090(19) _cell_length_c 21.432(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.41(3) _cell_angle_gamma 90.00 _cell_volume 2233.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3716 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 23.37 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex CCD' _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 8120 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0654 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.28 _reflns_number_total 4060 _reflns_number_gt 2951 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.048P)^2^+0.2891P] 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 4060 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0847(2) 1.0771(3) 0.13151(12) 0.0438(6) Uani 1 1 d . . . H1A H 1.1452 1.0519 0.1096 0.053 Uiso 1 1 calc R . . C2 C 1.0040(2) 0.9779(3) 0.14305(13) 0.0464(7) Uani 1 1 d . . . H2A H 1.0102 0.8842 0.1289 0.056 Uiso 1 1 calc R . . C3 C 0.9144(2) 1.0115(3) 0.17462(12) 0.0436(6) Uani 1 1 d . . . H3A H 0.8592 0.9420 0.1811 0.052 Uiso 1 1 calc R . . C4 C 0.9056(2) 1.1510(3) 0.19730(12) 0.0409(6) Uani 1 1 d . . . C5 C 0.9876(2) 1.2511(3) 0.18589(13) 0.0461(6) Uani 1 1 d . . . H5A H 0.9831 1.3443 0.2009 0.055 Uiso 1 1 calc R . . C6 C 1.0757(3) 1.2164(3) 0.15282(12) 0.0460(7) Uani 1 1 d . . . H6A H 1.1294 1.2861 0.1447 0.055 Uiso 1 1 calc R . . C7 C 0.8105(2) 1.1868(3) 0.23447(12) 0.0414(6) Uani 1 1 d . . . H7A H 0.8320 1.1474 0.2769 0.050 Uiso 1 1 calc R . . H7B H 0.8048 1.2903 0.2381 0.050 Uiso 1 1 calc R . . C8 C 0.6419(2) 1.0159(3) 0.22707(11) 0.0333(5) Uani 1 1 d . . . C9 C 0.5311(2) 0.9814(3) 0.17865(11) 0.0390(6) Uani 1 1 d . . . H9A H 0.4634 1.0311 0.1915 0.047 Uiso 1 1 calc R . . C10 C 0.5561(2) 1.0532(3) 0.11923(11) 0.0358(5) Uani 1 1 d . . . H10A H 0.6078 0.9890 0.1001 0.043 Uiso 1 1 calc R . . C11 C 0.6296(2) 1.1849(3) 0.14385(11) 0.0348(5) Uani 1 1 d . . . H11A H 0.6850 1.2092 0.1154 0.042 Uiso 1 1 calc R . . C12 C 0.4423(2) 1.0766(3) 0.07081(11) 0.0367(5) Uani 1 1 d . . . H12A H 0.4656 1.0917 0.0295 0.044 Uiso 1 1 calc R . . C13 C 0.3739(2) 1.2100(3) 0.08557(11) 0.0366(5) Uani 1 1 d . . . H13A H 0.3083 1.2285 0.0508 0.044 Uiso 1 1 calc R . . H13B H 0.3408 1.1935 0.1236 0.044 Uiso 1 1 calc R . . C14 C 0.4563(2) 1.3395(3) 0.09528(13) 0.0446(6) Uani 1 1 d . . . H14A H 0.4110 1.4249 0.1015 0.053 Uiso 1 1 calc R . . H14B H 0.4922 1.3539 0.0580 0.053 Uiso 1 1 calc R . . C15 C 0.5540(2) 1.3146(3) 0.15339(13) 0.0436(6) Uani 1 1 d . . . H15A H 0.6046 1.3990 0.1608 0.052 Uiso 1 1 calc R . . H15B H 0.5176 1.2997 0.1905 0.052 Uiso 1 1 calc R . . C16 C 0.4945(2) 0.8244(3) 0.16426(11) 0.0393(6) Uani 1 1 d . . . H16A H 0.4688 0.7842 0.2019 0.047 Uiso 1 1 calc R . . C17 C 0.3868(2) 0.8267(3) 0.11057(11) 0.0371(5) Uani 1 1 d . . . C18 C 0.3658(2) 0.9390(3) 0.06601(11) 0.0340(5) Uani 1 1 d . . . C19 C 0.2697(2) 0.9291(3) 0.01650(11) 0.0386(6) Uani 1 1 d . . . H19A H 0.2563 1.0029 -0.0132 0.046 Uiso 1 1 calc R . . C20 C 0.1932(2) 0.8130(3) 0.00981(11) 0.0366(5) Uani 1 1 d . . . H20A H 0.1302 0.8066 -0.0244 0.044 Uiso 1 1 calc R . . C21 C 0.2133(2) 0.7060(3) 0.05576(12) 0.0431(6) Uani 1 1 d . . . C22 C 0.3080(2) 0.7129(3) 0.10478(12) 0.0376(6) Uani 1 1 d . . . H22A H 0.3196 0.6396 0.1348 0.045 Uiso 1 1 calc R . . C23 C 0.5972(2) 0.7308(3) 0.14913(12) 0.0380(6) Uani 1 1 d . . . C24 C 0.6877(2) 0.6900(3) 0.19705(12) 0.0465(6) Uani 1 1 d . . . H24A H 0.6840 0.7136 0.2388 0.056 Uiso 1 1 calc R . . C25 C 0.7856(2) 0.6129(3) 0.18354(12) 0.0443(6) Uani 1 1 d . . . H25A H 0.8479 0.5882 0.2162 0.053 Uiso 1 1 calc R . . C26 C 0.7899(2) 0.5738(3) 0.12255(12) 0.0467(6) Uani 1 1 d . . . H26A H 0.8553 0.5230 0.1136 0.056 Uiso 1 1 calc R . . C27 C 0.6982(2) 0.6093(3) 0.07466(13) 0.0467(7) Uani 1 1 d . . . H27A H 0.6994 0.5796 0.0333 0.056 Uiso 1 1 calc R . . C28 C 0.6028(2) 0.6901(3) 0.08802(12) 0.0447(6) Uani 1 1 d . . . H28A H 0.5419 0.7170 0.0551 0.054 Uiso 1 1 calc R . . Cl1 Cl 0.11580(6) 0.56392(7) 0.04996(3) 0.04516(18) Uani 1 1 d . . . N1 N 0.69613(19) 1.1301(2) 0.20477(10) 0.0429(5) Uani 1 1 d . . . O1 O 0.67547(16) 0.9589(2) 0.27876(8) 0.0437(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0392(14) 0.0465(16) 0.0464(14) 0.0156(12) 0.0094(11) 0.0149(12) C2 0.0362(13) 0.0427(15) 0.0579(16) -0.0160(13) 0.0021(12) -0.0015(11) C3 0.0548(16) 0.0402(14) 0.0395(13) 0.0091(11) 0.0186(12) -0.0054(12) C4 0.0407(14) 0.0420(15) 0.0418(13) 0.0082(11) 0.0120(11) 0.0111(11) C5 0.0343(13) 0.0454(15) 0.0548(15) -0.0153(13) -0.0025(11) -0.0050(12) C6 0.0536(16) 0.0459(16) 0.0411(14) 0.0124(12) 0.0153(12) -0.0081(13) C7 0.0312(13) 0.0481(15) 0.0451(14) -0.0019(12) 0.0073(11) -0.0034(11) C8 0.0287(12) 0.0334(12) 0.0385(13) -0.0016(10) 0.0080(10) 0.0061(10) C9 0.0385(13) 0.0402(14) 0.0379(13) 0.0009(11) 0.0059(11) -0.0022(11) C10 0.0290(12) 0.0393(14) 0.0421(13) 0.0039(11) 0.0144(10) -0.0009(10) C11 0.0284(11) 0.0365(13) 0.0419(13) 0.0043(10) 0.0130(10) -0.0077(10) C12 0.0339(12) 0.0409(14) 0.0352(12) 0.0002(11) 0.0061(10) 0.0000(11) C13 0.0367(13) 0.0367(14) 0.0357(12) 0.0023(10) 0.0046(10) 0.0053(10) C14 0.0450(14) 0.0371(14) 0.0531(15) 0.0008(12) 0.0128(12) 0.0043(12) C15 0.0437(14) 0.0380(14) 0.0506(15) -0.0031(12) 0.0128(12) -0.0022(12) C16 0.0475(14) 0.0371(13) 0.0335(12) 0.0027(10) 0.0081(11) -0.0054(12) C17 0.0366(13) 0.0412(13) 0.0349(12) -0.0012(11) 0.0103(10) 0.0002(11) C18 0.0348(12) 0.0295(12) 0.0391(12) -0.0059(11) 0.0104(10) 0.0057(10) C19 0.0354(12) 0.0388(14) 0.0428(13) 0.0012(11) 0.0102(11) 0.0119(11) C20 0.0336(12) 0.0386(14) 0.0369(12) -0.0034(10) 0.0044(10) 0.0089(10) C21 0.0409(14) 0.0473(15) 0.0442(14) 0.0052(12) 0.0158(12) -0.0078(12) C22 0.0352(13) 0.0344(13) 0.0449(13) 0.0012(11) 0.0112(11) 0.0071(10) C23 0.0310(12) 0.0382(14) 0.0433(14) 0.0065(11) 0.0029(10) -0.0020(10) C24 0.0464(15) 0.0549(17) 0.0389(13) 0.0115(12) 0.0100(11) 0.0102(13) C25 0.0419(14) 0.0385(14) 0.0450(15) 0.0035(11) -0.0123(11) 0.0111(12) C26 0.0470(15) 0.0469(16) 0.0464(15) 0.0085(12) 0.0092(12) 0.0174(12) C27 0.0442(15) 0.0559(17) 0.0413(14) 0.0104(12) 0.0109(11) 0.0059(13) C28 0.0451(14) 0.0358(14) 0.0462(15) 0.0022(11) -0.0105(12) 0.0087(12) Cl1 0.0457(4) 0.0422(4) 0.0485(3) -0.0044(3) 0.0107(3) -0.0051(3) N1 0.0391(11) 0.0418(12) 0.0453(12) 0.0033(10) 0.0008(9) -0.0054(10) O1 0.0442(10) 0.0431(10) 0.0409(10) -0.0029(8) -0.0001(8) -0.0035(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.356(4) . ? C1 C6 1.385(4) . ? C1 H1A 0.9300 . ? C2 C3 1.358(4) . ? C2 H2A 0.9300 . ? C3 C4 1.396(4) . ? C3 H3A 0.9300 . ? C4 C5 1.372(4) . ? C4 C7 1.493(3) . ? C5 C6 1.368(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 N1 1.442(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O1 1.225(3) . ? C8 N1 1.359(3) . ? C8 C9 1.516(3) . ? C9 C10 1.510(3) . ? C9 C16 1.536(4) . ? C9 H9A 0.9800 . ? C10 C12 1.522(3) . ? C10 C11 1.523(3) . ? C10 H10A 0.9800 . ? C11 N1 1.477(3) . ? C11 C15 1.517(3) . ? C11 H11A 0.9800 . ? C12 C13 1.529(3) . ? C12 C18 1.541(3) . ? C12 H12A 0.9800 . ? C13 C14 1.518(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.530(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.522(4) . ? C16 C23 1.539(4) . ? C16 H16A 0.9800 . ? C17 C22 1.379(3) . ? C17 C18 1.407(3) . ? C18 C19 1.382(3) . ? C19 C20 1.379(4) . ? C19 H19A 0.9300 . ? C20 C21 1.391(3) . ? C20 H20A 0.9300 . ? C21 C22 1.364(4) . ? C21 Cl1 1.716(3) . ? C22 H22A 0.9300 . ? C23 C24 1.370(4) . ? C23 C28 1.376(4) . ? C24 C25 1.399(4) . ? C24 H24A 0.9300 . ? C25 C26 1.366(4) . ? C25 H25A 0.9300 . ? C26 C27 1.366(4) . ? C26 H26A 0.9300 . ? C27 C28 1.392(4) . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.9(2) . . ? C2 C1 H1A 120.5 . . ? C6 C1 H1A 120.5 . . ? C1 C2 C3 121.9(3) . . ? C1 C2 H2A 119.1 . . ? C3 C2 H2A 119.1 . . ? C2 C3 C4 119.7(2) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C5 C4 C3 118.4(2) . . ? C5 C4 C7 121.7(2) . . ? C3 C4 C7 119.9(2) . . ? C6 C5 C4 121.2(3) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C5 C6 C1 119.8(2) . . ? C5 C6 H6A 120.1 . . ? C1 C6 H6A 120.1 . . ? N1 C7 C4 111.5(2) . . ? N1 C7 H7A 109.3 . . ? C4 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C4 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? O1 C8 N1 124.7(2) . . ? O1 C8 C9 127.7(2) . . ? N1 C8 C9 107.4(2) . . ? C10 C9 C8 102.89(19) . . ? C10 C9 C16 109.7(2) . . ? C8 C9 C16 120.1(2) . . ? C10 C9 H9A 107.9 . . ? C8 C9 H9A 107.9 . . ? C16 C9 H9A 107.9 . . ? C9 C10 C12 111.78(19) . . ? C9 C10 C11 103.9(2) . . ? C12 C10 C11 117.9(2) . . ? C9 C10 H10A 107.6 . . ? C12 C10 H10A 107.6 . . ? C11 C10 H10A 107.6 . . ? N1 C11 C15 111.6(2) . . ? N1 C11 C10 100.95(19) . . ? C15 C11 C10 113.47(19) . . ? N1 C11 H11A 110.2 . . ? C15 C11 H11A 110.2 . . ? C10 C11 H11A 110.2 . . ? C10 C12 C13 112.2(2) . . ? C10 C12 C18 109.1(2) . . ? C13 C12 C18 112.70(18) . . ? C10 C12 H12A 107.5 . . ? C13 C12 H12A 107.5 . . ? C18 C12 H12A 107.5 . . ? C14 C13 C12 110.38(19) . . ? C14 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? C14 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C13 C14 C15 109.4(2) . . ? C13 C14 H14A 109.8 . . ? C15 C14 H14A 109.8 . . ? C13 C14 H14B 109.8 . . ? C15 C14 H14B 109.8 . . ? H14A C14 H14B 108.2 . . ? C11 C15 C14 110.9(2) . . ? C11 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C11 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.0 . . ? C17 C16 C9 106.9(2) . . ? C17 C16 C23 112.80(19) . . ? C9 C16 C23 113.1(2) . . ? C17 C16 H16A 108.0 . . ? C9 C16 H16A 108.0 . . ? C23 C16 H16A 108.0 . . ? C22 C17 C18 118.8(2) . . ? C22 C17 C16 118.6(2) . . ? C18 C17 C16 122.6(2) . . ? C19 C18 C17 119.0(2) . . ? C19 C18 C12 117.8(2) . . ? C17 C18 C12 123.2(2) . . ? C20 C19 C18 122.0(2) . . ? C20 C19 H19A 119.0 . . ? C18 C19 H19A 119.0 . . ? C19 C20 C21 117.9(2) . . ? C19 C20 H20A 121.0 . . ? C21 C20 H20A 121.0 . . ? C22 C21 C20 121.2(2) . . ? C22 C21 Cl1 120.2(2) . . ? C20 C21 Cl1 118.7(2) . . ? C21 C22 C17 121.1(2) . . ? C21 C22 H22A 119.5 . . ? C17 C22 H22A 119.5 . . ? C24 C23 C28 118.7(2) . . ? C24 C23 C16 119.7(2) . . ? C28 C23 C16 121.6(2) . . ? C23 C24 C25 120.4(2) . . ? C23 C24 H24A 119.8 . . ? C25 C24 H24A 119.8 . . ? C26 C25 C24 120.2(2) . . ? C26 C25 H25A 119.9 . . ? C24 C25 H25A 119.9 . . ? C27 C26 C25 120.0(2) . . ? C27 C26 H26A 120.0 . . ? C25 C26 H26A 120.0 . . ? C26 C27 C28 119.7(3) . . ? C26 C27 H27A 120.2 . . ? C28 C27 H27A 120.2 . . ? C23 C28 C27 121.1(2) . . ? C23 C28 H28A 119.5 . . ? C27 C28 H28A 119.5 . . ? C8 N1 C7 124.2(2) . . ? C8 N1 C11 112.84(19) . . ? C7 N1 C11 122.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.3(4) . . . . ? C1 C2 C3 C4 -1.4(4) . . . . ? C2 C3 C4 C5 1.1(4) . . . . ? C2 C3 C4 C7 -177.3(3) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C7 C4 C5 C6 178.7(2) . . . . ? C4 C5 C6 C1 -1.5(4) . . . . ? C2 C1 C6 C5 1.1(4) . . . . ? C5 C4 C7 N1 135.7(3) . . . . ? C3 C4 C7 N1 -46.0(3) . . . . ? O1 C8 C9 C10 -164.3(2) . . . . ? N1 C8 C9 C10 19.5(3) . . . . ? O1 C8 C9 C16 -42.1(3) . . . . ? N1 C8 C9 C16 141.7(2) . . . . ? C8 C9 C10 C12 -160.7(2) . . . . ? C16 C9 C10 C12 70.4(3) . . . . ? C8 C9 C10 C11 -32.6(2) . . . . ? C16 C9 C10 C11 -161.5(2) . . . . ? C9 C10 C11 N1 33.1(2) . . . . ? C12 C10 C11 N1 157.31(19) . . . . ? C9 C10 C11 C15 -86.5(2) . . . . ? C12 C10 C11 C15 37.8(3) . . . . ? C9 C10 C12 C13 80.9(3) . . . . ? C11 C10 C12 C13 -39.3(3) . . . . ? C9 C10 C12 C18 -44.7(3) . . . . ? C11 C10 C12 C18 -164.90(19) . . . . ? C10 C12 C13 C14 51.5(3) . . . . ? C18 C12 C13 C14 175.19(19) . . . . ? C12 C13 C14 C15 -63.7(3) . . . . ? N1 C11 C15 C14 -161.1(2) . . . . ? C10 C11 C15 C14 -47.9(3) . . . . ? C13 C14 C15 C11 61.7(3) . . . . ? C10 C9 C16 C17 -56.8(3) . . . . ? C8 C9 C16 C17 -175.6(2) . . . . ? C10 C9 C16 C23 67.9(3) . . . . ? C8 C9 C16 C23 -50.9(3) . . . . ? C9 C16 C17 C22 -154.6(2) . . . . ? C23 C16 C17 C22 80.6(3) . . . . ? C9 C16 C17 C18 26.6(3) . . . . ? C23 C16 C17 C18 -98.2(3) . . . . ? C22 C17 C18 C19 -2.5(3) . . . . ? C16 C17 C18 C19 176.3(2) . . . . ? C22 C17 C18 C12 175.2(2) . . . . ? C16 C17 C18 C12 -6.0(3) . . . . ? C10 C12 C18 C19 -168.38(19) . . . . ? C13 C12 C18 C19 66.3(3) . . . . ? C10 C12 C18 C17 13.9(3) . . . . ? C13 C12 C18 C17 -111.5(2) . . . . ? C17 C18 C19 C20 0.6(3) . . . . ? C12 C18 C19 C20 -177.2(2) . . . . ? C18 C19 C20 C21 1.7(3) . . . . ? C19 C20 C21 C22 -2.2(4) . . . . ? C19 C20 C21 Cl1 177.59(17) . . . . ? C20 C21 C22 C17 0.3(4) . . . . ? Cl1 C21 C22 C17 -179.48(18) . . . . ? C18 C17 C22 C21 2.1(3) . . . . ? C16 C17 C22 C21 -176.8(2) . . . . ? C17 C16 C23 C24 -164.6(2) . . . . ? C9 C16 C23 C24 74.0(3) . . . . ? C17 C16 C23 C28 17.4(3) . . . . ? C9 C16 C23 C28 -104.1(3) . . . . ? C28 C23 C24 C25 2.3(4) . . . . ? C16 C23 C24 C25 -175.8(2) . . . . ? C23 C24 C25 C26 -2.1(4) . . . . ? C24 C25 C26 C27 -0.4(4) . . . . ? C25 C26 C27 C28 2.5(4) . . . . ? C24 C23 C28 C27 -0.1(4) . . . . ? C16 C23 C28 C27 177.9(2) . . . . ? C26 C27 C28 C23 -2.3(4) . . . . ? O1 C8 N1 C7 9.7(4) . . . . ? C9 C8 N1 C7 -173.9(2) . . . . ? O1 C8 N1 C11 -174.4(2) . . . . ? C9 C8 N1 C11 2.0(3) . . . . ? C4 C7 N1 C8 107.1(3) . . . . ? C4 C7 N1 C11 -68.4(3) . . . . ? C15 C11 N1 C8 98.6(2) . . . . ? C10 C11 N1 C8 -22.3(2) . . . . ? C15 C11 N1 C7 -85.4(3) . . . . ? C10 C11 N1 C7 153.7(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.172 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.042 ##################END # Attachment '715804cif.txt' data_CCDC-715804 _database_code_depnum_ccdc_archive 'CCDC 715804' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 11-Acetyl-6-benzyl-8-phenyl-1,2,3,4,5,5a,6,7a,8,12b- decahydrobenzo(f)cycloocta(c ; _chemical_melting_point 499K _chemical_formula_moiety 'C32 H33 N O2' _chemical_formula_sum 'C32 H33 N O2' _chemical_formula_weight 463.59 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' N N 0.0061 0.0033 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3312(15) _cell_length_b 11.398(2) _cell_length_c 11.5132(13) _cell_angle_alpha 78.511(2) _cell_angle_beta 83.442(3) _cell_angle_gamma 69.991(2) _cell_volume 1246.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3319 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 23.91 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9776 _exptl_absorpt_correction_T_max 0.9924 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _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 9054 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.26 _reflns_number_total 4527 _reflns_number_gt 3380 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.04P)^2^+0.22P] 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 4527 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4522(2) -0.3298(2) 0.87027(19) 0.0567(5) Uani 1 1 d . . . H1A H 0.4845 -0.3854 0.8129 0.085 Uiso 1 1 calc R . . H1B H 0.4013 -0.3655 0.9341 0.085 Uiso 1 1 calc R . . H1C H 0.5296 -0.3196 0.9009 0.085 Uiso 1 1 calc R . . C2 C 0.3602(2) -0.20269(19) 0.81215(18) 0.0477(5) Uani 1 1 d . . . C3 C 0.29882(19) -0.09987(17) 0.88404(17) 0.0425(4) Uani 1 1 d . . . C4 C 0.35081(19) -0.09905(16) 0.98912(17) 0.0447(4) Uani 1 1 d . . . H4A H 0.4327 -0.1613 1.0140 0.054 Uiso 1 1 calc R . . C5 C 0.28334(19) -0.00747(16) 1.05772(16) 0.0422(4) Uani 1 1 d . . . H5A H 0.3209 -0.0076 1.1274 0.051 Uiso 1 1 calc R . . C6 C 0.15877(18) 0.08552(17) 1.02302(15) 0.0404(4) Uani 1 1 d . . . C7 C 0.10626(17) 0.08722(17) 0.91417(15) 0.0385(4) Uani 1 1 d . . . C8 C 0.17680(18) -0.00280(15) 0.84679(15) 0.0369(4) Uani 1 1 d . . . H8A H 0.1433 0.0001 0.7743 0.044 Uiso 1 1 calc R . . C9 C 0.0727(2) 0.18507(18) 1.09420(15) 0.0447(5) Uani 1 1 d . . . H9A H -0.0159 0.1696 1.1093 0.054 Uiso 1 1 calc R . . C11 C 0.03791(19) 0.31754(18) 1.01174(16) 0.0451(5) Uani 1 1 d . . . H11A H -0.0304 0.3796 1.0547 0.054 Uiso 1 1 calc R . . C12 C -0.0260(2) 0.31866(18) 0.89473(16) 0.0463(5) Uani 1 1 d . . . H12A H -0.1203 0.3786 0.8934 0.056 Uiso 1 1 calc R . . C13 C -0.03188(18) 0.18771(17) 0.88440(16) 0.0407(4) Uani 1 1 d . . . H13A H -0.1000 0.1690 0.9451 0.049 Uiso 1 1 calc R . . C14 C 0.05976(19) 0.36884(18) 0.79239(16) 0.0440(4) Uani 1 1 d . . . H14A H 0.1074 0.3009 0.7467 0.053 Uiso 1 1 calc R . . C15 C -0.0252(2) 0.48447(19) 0.70803(18) 0.0504(5) Uani 1 1 d . . . H15A H -0.0800 0.5478 0.7550 0.060 Uiso 1 1 calc R . . H15B H 0.0381 0.5199 0.6564 0.060 Uiso 1 1 calc R . . C16 C -0.12042(18) 0.46233(18) 0.63156(15) 0.0422(4) Uani 1 1 d . . . H16A H -0.0666 0.3961 0.5872 0.051 Uiso 1 1 calc R . . H16B H -0.1571 0.5391 0.5746 0.051 Uiso 1 1 calc R . . C17 C -0.2414(2) 0.42486(19) 0.69700(18) 0.0504(5) Uani 1 1 d . . . H17A H -0.3208 0.4656 0.6485 0.060 Uiso 1 1 calc R . . H17B H -0.2631 0.4598 0.7698 0.060 Uiso 1 1 calc R . . C18 C -0.22405(19) 0.28292(18) 0.72945(17) 0.0455(5) Uani 1 1 d . . . H18A H -0.2513 0.2585 0.6624 0.055 Uiso 1 1 calc R . . H18B H -0.2892 0.2727 0.7951 0.055 Uiso 1 1 calc R . . C19 C -0.08136(19) 0.18747(17) 0.76385(16) 0.0408(4) Uani 1 1 d . . . H19A H -0.0829 0.1030 0.7630 0.049 Uiso 1 1 calc R . . H19B H -0.0137 0.2038 0.7029 0.049 Uiso 1 1 calc R . . C20 C 0.11768(19) 0.17971(17) 1.21796(15) 0.0435(4) Uani 1 1 d . . . C21 C 0.02192(19) 0.16842(18) 1.31302(16) 0.0447(4) Uani 1 1 d . . . H21A H -0.0634 0.1645 1.2994 0.054 Uiso 1 1 calc R . . C22 C 0.0565(2) 0.16323(18) 1.42757(16) 0.0472(5) Uani 1 1 d . . . H22A H -0.0064 0.1563 1.4910 0.057 Uiso 1 1 calc R . . C23 C 0.1832(2) 0.16830(18) 1.44797(16) 0.0468(5) Uani 1 1 d . . . H23A H 0.2054 0.1649 1.5249 0.056 Uiso 1 1 calc R . . C24 C 0.2755(2) 0.17826(18) 1.35608(17) 0.0469(5) Uani 1 1 d . . . H24A H 0.3609 0.1813 1.3707 0.056 Uiso 1 1 calc R . . C25 C 0.2446(2) 0.18394(18) 1.24109(16) 0.0463(5) Uani 1 1 d . . . H25A H 0.3091 0.1906 1.1790 0.056 Uiso 1 1 calc R . . C26 C 0.1580(2) 0.36617(18) 0.97039(17) 0.0471(5) Uani 1 1 d . . . C27 C 0.27445(19) 0.43631(17) 0.78501(17) 0.0431(4) Uani 1 1 d . . . H27A H 0.3314 0.4475 0.8406 0.052 Uiso 1 1 calc R . . H27B H 0.2353 0.5174 0.7345 0.052 Uiso 1 1 calc R . . C28 C 0.36238(19) 0.34208(17) 0.71031(17) 0.0435(4) Uani 1 1 d . . . C29 C 0.3980(2) 0.21271(19) 0.74919(18) 0.0494(5) Uani 1 1 d . . . H29A H 0.3658 0.1824 0.8239 0.059 Uiso 1 1 calc R . . C30 C 0.48090(19) 0.12752(19) 0.67877(17) 0.0463(5) Uani 1 1 d . . . H30A H 0.5027 0.0409 0.7062 0.056 Uiso 1 1 calc R . . C31 C 0.53043(18) 0.16953(17) 0.57030(17) 0.0428(4) Uani 1 1 d . . . H31A H 0.5864 0.1119 0.5236 0.051 Uiso 1 1 calc R . . C32 C 0.49759(18) 0.29812(17) 0.52920(16) 0.0400(4) Uani 1 1 d . . . H32A H 0.5321 0.3275 0.4551 0.048 Uiso 1 1 calc R . . C33 C 0.41303(19) 0.38309(18) 0.59897(16) 0.0450(4) Uani 1 1 d . . . H33A H 0.3898 0.4696 0.5703 0.054 Uiso 1 1 calc R . . N1 N 0.16349(15) 0.39594(13) 0.85050(13) 0.0391(3) Uani 1 1 d . . . O1 O 0.33052(14) -0.18795(13) 0.71066(13) 0.0525(4) Uani 1 1 d . . . O2 O 0.23758(14) 0.38107(13) 1.03277(12) 0.0518(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0504(12) 0.0543(13) 0.0538(12) -0.0136(10) -0.0013(10) -0.0006(10) C2 0.0421(10) 0.0475(11) 0.0440(11) -0.0093(8) 0.0038(8) -0.0035(9) C3 0.0392(9) 0.0344(9) 0.0466(10) -0.0075(8) -0.0043(8) -0.0018(8) C4 0.0443(10) 0.0291(9) 0.0487(11) -0.0057(8) -0.0125(8) 0.0059(8) C5 0.0484(10) 0.0304(9) 0.0366(9) -0.0032(7) -0.0139(8) 0.0036(8) C6 0.0390(9) 0.0395(10) 0.0348(9) -0.0016(7) -0.0057(7) -0.0045(8) C7 0.0328(9) 0.0407(10) 0.0325(9) -0.0023(7) -0.0038(7) -0.0018(7) C8 0.0425(9) 0.0295(9) 0.0327(9) -0.0020(7) -0.0057(7) -0.0051(7) C9 0.0456(10) 0.0446(11) 0.0323(9) -0.0044(8) -0.0068(8) 0.0001(8) C11 0.0396(10) 0.0417(10) 0.0377(10) -0.0056(8) -0.0064(8) 0.0080(8) C12 0.0511(11) 0.0399(10) 0.0448(11) 0.0056(8) -0.0148(9) -0.0142(9) C13 0.0356(9) 0.0399(10) 0.0378(9) -0.0034(7) -0.0087(7) -0.0006(8) C14 0.0416(10) 0.0457(11) 0.0364(10) -0.0035(8) -0.0059(8) -0.0044(8) C15 0.0477(11) 0.0499(12) 0.0516(11) 0.0089(9) -0.0152(9) -0.0192(9) C16 0.0428(10) 0.0404(10) 0.0348(9) -0.0004(7) -0.0104(8) -0.0034(8) C17 0.0510(11) 0.0522(12) 0.0520(12) -0.0013(9) -0.0208(9) -0.0205(9) C18 0.0412(10) 0.0522(11) 0.0449(10) 0.0042(8) -0.0199(8) -0.0191(9) C19 0.0459(10) 0.0322(9) 0.0418(10) -0.0012(7) -0.0176(8) -0.0077(8) C20 0.0433(10) 0.0394(10) 0.0333(9) -0.0057(7) -0.0093(8) 0.0069(8) C21 0.0412(10) 0.0457(11) 0.0401(10) 0.0038(8) -0.0198(8) -0.0057(8) C22 0.0485(11) 0.0467(11) 0.0340(9) -0.0028(8) -0.0061(8) -0.0011(9) C23 0.0519(11) 0.0397(10) 0.0340(9) 0.0083(8) -0.0246(8) 0.0028(8) C24 0.0438(10) 0.0465(11) 0.0451(11) 0.0044(8) -0.0253(9) -0.0074(8) C25 0.0459(10) 0.0468(11) 0.0335(9) -0.0025(8) -0.0047(8) -0.0006(8) C26 0.0527(11) 0.0387(10) 0.0424(10) -0.0053(8) -0.0141(9) -0.0026(8) C27 0.0482(10) 0.0352(10) 0.0454(10) -0.0029(8) -0.0015(8) -0.0154(8) C28 0.0411(10) 0.0374(10) 0.0467(11) -0.0038(8) -0.0094(8) -0.0057(8) C29 0.0526(11) 0.0447(11) 0.0505(12) 0.0013(9) -0.0022(9) -0.0208(9) C30 0.0433(10) 0.0433(11) 0.0456(11) 0.0046(8) -0.0238(8) -0.0056(8) C31 0.0381(9) 0.0401(10) 0.0452(10) -0.0121(8) -0.0113(8) -0.0007(8) C32 0.0388(9) 0.0459(10) 0.0396(9) 0.0020(8) -0.0125(8) -0.0212(8) C33 0.0439(10) 0.0430(10) 0.0423(10) 0.0058(8) -0.0215(8) -0.0081(8) N1 0.0395(8) 0.0317(8) 0.0385(8) -0.0050(6) -0.0014(6) -0.0029(6) O1 0.0535(8) 0.0461(8) 0.0518(8) -0.0032(6) -0.0054(6) -0.0108(6) O2 0.0516(8) 0.0528(8) 0.0547(8) 0.0016(6) -0.0037(7) -0.0273(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.506(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 O1 1.207(2) . ? C2 C3 1.489(3) . ? C3 C4 1.382(3) . ? C3 C8 1.406(2) . ? C4 C5 1.380(2) . ? C4 H4A 0.9300 . ? C5 C6 1.398(2) . ? C5 H5A 0.9300 . ? C6 C7 1.415(2) . ? C6 C9 1.504(2) . ? C7 C8 1.365(2) . ? C7 C13 1.517(2) . ? C8 H8A 0.9300 . ? C9 C20 1.532(2) . ? C9 C11 1.564(3) . ? C9 H9A 0.9800 . ? C11 C26 1.517(3) . ? C11 C12 1.562(3) . ? C11 H11A 0.9800 . ? C12 C14 1.530(3) . ? C12 C13 1.543(3) . ? C12 H12A 0.9800 . ? C13 C19 1.534(2) . ? C13 H13A 0.9800 . ? C14 N1 1.471(2) . ? C14 C15 1.531(2) . ? C14 H14A 0.9800 . ? C15 C16 1.504(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.528(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.538(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.542(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C25 1.386(3) . ? C20 C21 1.406(3) . ? C21 C22 1.390(2) . ? C21 H21A 0.9300 . ? C22 C23 1.378(3) . ? C22 H22A 0.9300 . ? C23 C24 1.356(3) . ? C23 H23A 0.9300 . ? C24 C25 1.381(3) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C26 O2 1.225(2) . ? C26 N1 1.354(2) . ? C27 N1 1.456(2) . ? C27 C28 1.497(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C33 1.382(3) . ? C28 C29 1.383(3) . ? C29 C30 1.385(3) . ? C29 H29A 0.9300 . ? C30 C31 1.354(3) . ? C30 H30A 0.9300 . ? C31 C32 1.381(3) . ? C31 H31A 0.9300 . ? C32 C33 1.385(3) . ? C32 H32A 0.9300 . ? C33 H33A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 120.96(18) . . ? O1 C2 C1 119.73(18) . . ? C3 C2 C1 119.16(17) . . ? C4 C3 C8 118.30(16) . . ? C4 C3 C2 123.38(16) . . ? C8 C3 C2 118.20(17) . . ? C5 C4 C3 121.13(16) . . ? C5 C4 H4A 119.4 . . ? C3 C4 H4A 119.4 . . ? C4 C5 C6 120.35(17) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C5 C6 C7 118.92(16) . . ? C5 C6 C9 124.80(16) . . ? C7 C6 C9 116.27(15) . . ? C8 C7 C6 119.43(15) . . ? C8 C7 C13 124.46(16) . . ? C6 C7 C13 116.01(15) . . ? C7 C8 C3 121.76(16) . . ? C7 C8 H8A 119.1 . . ? C3 C8 H8A 119.1 . . ? C6 C9 C20 118.36(15) . . ? C6 C9 C11 108.60(15) . . ? C20 C9 C11 115.54(16) . . ? C6 C9 H9A 104.2 . . ? C20 C9 H9A 104.2 . . ? C11 C9 H9A 104.2 . . ? C26 C11 C12 104.53(15) . . ? C26 C11 C9 116.34(15) . . ? C12 C11 C9 111.92(16) . . ? C26 C11 H11A 107.9 . . ? C12 C11 H11A 107.9 . . ? C9 C11 H11A 107.9 . . ? C14 C12 C13 112.40(16) . . ? C14 C12 C11 106.56(15) . . ? C13 C12 C11 112.87(14) . . ? C14 C12 H12A 108.3 . . ? C13 C12 H12A 108.3 . . ? C11 C12 H12A 108.3 . . ? C7 C13 C19 113.63(15) . . ? C7 C13 C12 109.47(15) . . ? C19 C13 C12 112.11(14) . . ? C7 C13 H13A 107.1 . . ? C19 C13 H13A 107.1 . . ? C12 C13 H13A 107.1 . . ? N1 C14 C12 104.62(14) . . ? N1 C14 C15 112.54(16) . . ? C12 C14 C15 113.88(16) . . ? N1 C14 H14A 108.5 . . ? C12 C14 H14A 108.5 . . ? C15 C14 H14A 108.5 . . ? C16 C15 C14 116.67(17) . . ? C16 C15 H15A 108.1 . . ? C14 C15 H15A 108.1 . . ? C16 C15 H15B 108.1 . . ? C14 C15 H15B 108.1 . . ? H15A C15 H15B 107.3 . . ? C15 C16 C17 115.89(16) . . ? C15 C16 H16A 108.3 . . ? C17 C16 H16A 108.3 . . ? C15 C16 H16B 108.3 . . ? C17 C16 H16B 108.3 . . ? H16A C16 H16B 107.4 . . ? C16 C17 C18 117.97(17) . . ? C16 C17 H17A 107.8 . . ? C18 C17 H17A 107.8 . . ? C16 C17 H17B 107.8 . . ? C18 C17 H17B 107.8 . . ? H17A C17 H17B 107.2 . . ? C17 C18 C19 119.06(15) . . ? C17 C18 H18A 107.6 . . ? C19 C18 H18A 107.6 . . ? C17 C18 H18B 107.6 . . ? C19 C18 H18B 107.6 . . ? H18A C18 H18B 107.0 . . ? C13 C19 C18 116.84(15) . . ? C13 C19 H19A 108.1 . . ? C18 C19 H19A 108.1 . . ? C13 C19 H19B 108.1 . . ? C18 C19 H19B 108.1 . . ? H19A C19 H19B 107.3 . . ? C25 C20 C21 119.13(16) . . ? C25 C20 C9 124.55(17) . . ? C21 C20 C9 116.31(17) . . ? C22 C21 C20 119.12(18) . . ? C22 C21 H21A 120.4 . . ? C20 C21 H21A 120.4 . . ? C23 C22 C21 120.53(19) . . ? C23 C22 H22A 119.7 . . ? C21 C22 H22A 119.7 . . ? C24 C23 C22 120.11(17) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C23 C24 C25 120.95(18) . . ? C23 C24 H24A 119.5 . . ? C25 C24 H24A 119.5 . . ? C24 C25 C20 120.15(18) . . ? C24 C25 H25A 119.9 . . ? C20 C25 H25A 119.9 . . ? O2 C26 N1 123.32(19) . . ? O2 C26 C11 127.09(18) . . ? N1 C26 C11 109.56(16) . . ? N1 C27 C28 111.80(15) . . ? N1 C27 H27A 109.3 . . ? C28 C27 H27A 109.3 . . ? N1 C27 H27B 109.3 . . ? C28 C27 H27B 109.3 . . ? H27A C27 H27B 107.9 . . ? C33 C28 C29 117.55(18) . . ? C33 C28 C27 120.13(17) . . ? C29 C28 C27 122.31(18) . . ? C28 C29 C30 121.14(19) . . ? C28 C29 H29A 119.4 . . ? C30 C29 H29A 119.4 . . ? C31 C30 C29 120.45(18) . . ? C31 C30 H30A 119.8 . . ? C29 C30 H30A 119.8 . . ? C30 C31 C32 119.86(18) . . ? C30 C31 H31A 120.1 . . ? C32 C31 H31A 120.1 . . ? C31 C32 C33 119.61(17) . . ? C31 C32 H32A 120.2 . . ? C33 C32 H32A 120.2 . . ? C28 C33 C32 121.39(18) . . ? C28 C33 H33A 119.3 . . ? C32 C33 H33A 119.3 . . ? C26 N1 C27 121.90(16) . . ? C26 N1 C14 114.67(16) . . ? C27 N1 C14 122.99(14) . . ? 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 C2 C3 C4 -164.6(2) . . . . ? C1 C2 C3 C4 20.0(3) . . . . ? O1 C2 C3 C8 19.5(3) . . . . ? C1 C2 C3 C8 -155.94(18) . . . . ? C8 C3 C4 C5 1.7(3) . . . . ? C2 C3 C4 C5 -174.28(19) . . . . ? C3 C4 C5 C6 1.2(3) . . . . ? C4 C5 C6 C7 -2.6(3) . . . . ? C4 C5 C6 C9 176.37(19) . . . . ? C5 C6 C7 C8 1.1(3) . . . . ? C9 C6 C7 C8 -177.97(17) . . . . ? C5 C6 C7 C13 177.84(17) . . . . ? C9 C6 C7 C13 -1.2(2) . . . . ? C6 C7 C8 C3 1.8(3) . . . . ? C13 C7 C8 C3 -174.63(17) . . . . ? C4 C3 C8 C7 -3.2(3) . . . . ? C2 C3 C8 C7 172.95(17) . . . . ? C5 C6 C9 C20 -4.7(3) . . . . ? C7 C6 C9 C20 174.27(17) . . . . ? C5 C6 C9 C11 129.58(19) . . . . ? C7 C6 C9 C11 -51.4(2) . . . . ? C6 C9 C11 C26 -68.0(2) . . . . ? C20 C9 C11 C26 67.8(2) . . . . ? C6 C9 C11 C12 52.1(2) . . . . ? C20 C9 C11 C12 -172.16(16) . . . . ? C26 C11 C12 C14 -0.47(19) . . . . ? C9 C11 C12 C14 -127.22(16) . . . . ? C26 C11 C12 C13 123.36(17) . . . . ? C9 C11 C12 C13 -3.4(2) . . . . ? C8 C7 C13 C19 -5.2(3) . . . . ? C6 C7 C13 C19 178.26(16) . . . . ? C8 C7 C13 C12 -131.38(19) . . . . ? C6 C7 C13 C12 52.1(2) . . . . ? C14 C12 C13 C7 73.27(18) . . . . ? C11 C12 C13 C7 -47.3(2) . . . . ? C14 C12 C13 C19 -53.8(2) . . . . ? C11 C12 C13 C19 -174.33(15) . . . . ? C13 C12 C14 N1 -125.08(15) . . . . ? C11 C12 C14 N1 -0.96(18) . . . . ? C13 C12 C14 C15 111.64(18) . . . . ? C11 C12 C14 C15 -124.23(17) . . . . ? N1 C14 C15 C16 171.78(16) . . . . ? C12 C14 C15 C16 -69.4(2) . . . . ? C14 C15 C16 C17 66.6(2) . . . . ? C15 C16 C17 C18 -95.1(2) . . . . ? C16 C17 C18 C19 34.9(3) . . . . ? C7 C13 C19 C18 177.36(16) . . . . ? C12 C13 C19 C18 -57.9(2) . . . . ? C17 C18 C19 C13 71.3(2) . . . . ? C6 C9 C20 C25 58.2(3) . . . . ? C11 C9 C20 C25 -73.1(2) . . . . ? C6 C9 C20 C21 -121.15(19) . . . . ? C11 C9 C20 C21 107.6(2) . . . . ? C25 C20 C21 C22 0.7(3) . . . . ? C9 C20 C21 C22 -179.92(16) . . . . ? C20 C21 C22 C23 -0.4(3) . . . . ? C21 C22 C23 C24 -0.1(3) . . . . ? C22 C23 C24 C25 0.2(3) . . . . ? C23 C24 C25 C20 0.1(3) . . . . ? C21 C20 C25 C24 -0.6(3) . . . . ? C9 C20 C25 C24 -179.90(17) . . . . ? C12 C11 C26 O2 179.96(18) . . . . ? C9 C11 C26 O2 -56.1(3) . . . . ? C12 C11 C26 N1 1.9(2) . . . . ? C9 C11 C26 N1 125.84(16) . . . . ? N1 C27 C28 C33 141.88(17) . . . . ? N1 C27 C28 C29 -39.2(2) . . . . ? C33 C28 C29 C30 -0.3(3) . . . . ? C27 C28 C29 C30 -179.25(17) . . . . ? C28 C29 C30 C31 0.8(3) . . . . ? C29 C30 C31 C32 -0.4(3) . . . . ? C30 C31 C32 C33 -0.6(3) . . . . ? C29 C28 C33 C32 -0.7(3) . . . . ? C27 C28 C33 C32 178.27(16) . . . . ? C31 C32 C33 C28 1.2(3) . . . . ? O2 C26 N1 C27 6.5(3) . . . . ? C11 C26 N1 C27 -175.36(15) . . . . ? O2 C26 N1 C14 179.11(17) . . . . ? C11 C26 N1 C14 -2.7(2) . . . . ? C28 C27 N1 C26 114.01(18) . . . . ? C28 C27 N1 C14 -58.0(2) . . . . ? C12 C14 N1 C26 2.3(2) . . . . ? C15 C14 N1 C26 126.47(18) . . . . ? C12 C14 N1 C27 174.87(15) . . . . ? C15 C14 N1 C27 -61.0(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.26 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.150 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.032 ##################END # Attachment '715805cif.txt' data_CCDC-715805 _database_code_depnum_ccdc_archive 'CCDC 715805' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; 4-Benzyl-9-chloro-1,2,3,3a,4,5a,6,10b-octahydronaphtho(3,2,1- cd)indol-5(3a1H)-on ; _chemical_melting_point 437K _chemical_formula_moiety 'C22 H22 Cl N O' _chemical_formula_sum 'C22 H22 Cl N O' _chemical_formula_weight 351.86 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' N N 0.0061 0.0033 '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)/n ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4020(14) _cell_length_b 20.083(3) _cell_length_c 10.376(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.161(7) _cell_angle_gamma 90.00 _cell_volume 1787.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3875 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 23.18 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _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 6500 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.27 _reflns_number_total 3250 _reflns_number_gt 2233 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0552P)^2^] 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 3250 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1254 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1037(3) 0.41727(13) 0.0751(3) 0.0438(6) Uani 1 1 d . . . H1A H -0.1910 0.4037 -0.0035 0.053 Uiso 1 1 calc R . . C2 C 0.0365(3) 0.42019(14) 0.0686(3) 0.0481(7) Uani 1 1 d . . . H2A H 0.0447 0.4083 -0.0147 0.058 Uiso 1 1 calc R . . C3 C 0.1678(3) 0.44042(13) 0.1831(3) 0.0428(6) Uani 1 1 d . . . H3A H 0.2634 0.4429 0.1766 0.051 Uiso 1 1 calc R . . C4 C 0.1563(3) 0.45688(14) 0.3067(3) 0.0434(6) Uani 1 1 d . . . C5 C 0.0126(3) 0.45328(14) 0.3136(3) 0.0485(7) Uani 1 1 d . . . H5A H 0.0042 0.4638 0.3975 0.058 Uiso 1 1 calc R . . C6 C -0.1179(3) 0.43430(13) 0.1978(3) 0.0439(6) Uani 1 1 d . . . H6A H -0.2147 0.4330 0.2023 0.053 Uiso 1 1 calc R . . C7 C 0.3008(3) 0.47829(14) 0.4314(3) 0.0454(6) Uani 1 1 d . . . H7A H 0.3888 0.4769 0.4054 0.055 Uiso 1 1 calc R . . H7B H 0.2880 0.5240 0.4549 0.055 Uiso 1 1 calc R . . C8 C 0.3370(3) 0.36338(13) 0.5476(3) 0.0425(6) Uani 1 1 d . . . H8A H 0.2419 0.3471 0.4703 0.051 Uiso 1 1 calc R . . C9 C 0.3342(3) 0.34645(13) 0.6893(3) 0.0400(6) Uani 1 1 d . . . H9A H 0.2275 0.3528 0.6812 0.048 Uiso 1 1 calc R . . C10 C 0.4352(3) 0.40027(13) 0.7842(3) 0.0400(6) Uani 1 1 d . . . H10A H 0.5434 0.3887 0.8040 0.048 Uiso 1 1 calc R . . C11 C 0.3945(3) 0.45996(13) 0.6880(3) 0.0415(6) Uani 1 1 d . . . C12 C 0.4800(3) 0.33764(13) 0.5303(3) 0.0452(6) Uani 1 1 d . . . H12A H 0.5706 0.3633 0.5897 0.054 Uiso 1 1 calc R . . H12B H 0.4659 0.3432 0.4330 0.054 Uiso 1 1 calc R . . C13 C 0.5072(3) 0.26351(14) 0.5714(3) 0.0443(6) Uani 1 1 d . . . H13A H 0.4180 0.2376 0.5102 0.053 Uiso 1 1 calc R . . H13B H 0.5983 0.2477 0.5590 0.053 Uiso 1 1 calc R . . C14 C 0.5313(3) 0.25423(14) 0.7252(3) 0.0429(6) Uani 1 1 d . . . H14A H 0.6216 0.2796 0.7861 0.052 Uiso 1 1 calc R . . H14B H 0.5513 0.2076 0.7507 0.052 Uiso 1 1 calc R . . C15 C 0.3872(3) 0.27728(13) 0.7481(3) 0.0403(6) Uani 1 1 d . . . H15A H 0.3021 0.2464 0.6966 0.048 Uiso 1 1 calc R . . C16 C 0.4125(3) 0.27540(12) 0.9028(3) 0.0400(6) Uani 1 1 d . . . C17 C 0.4351(3) 0.33301(13) 0.9848(3) 0.0436(6) Uani 1 1 d . . . C18 C 0.4229(3) 0.40244(13) 0.9225(3) 0.0410(6) Uani 1 1 d . . . H18A H 0.3239 0.4221 0.9100 0.049 Uiso 1 1 calc R . . H18B H 0.5054 0.4302 0.9876 0.049 Uiso 1 1 calc R . . C19 C 0.4099(3) 0.21371(13) 0.9631(3) 0.0468(7) Uani 1 1 d . . . H19A H 0.3893 0.1753 0.9084 0.056 Uiso 1 1 calc R . . C20 C 0.4378(3) 0.20961(14) 1.1039(3) 0.0461(6) Uani 1 1 d . . . C21 C 0.4684(3) 0.26479(15) 1.1869(3) 0.0449(6) Uani 1 1 d . . . H21A H 0.4895 0.2613 1.2823 0.054 Uiso 1 1 calc R . . C22 C 0.4676(3) 0.32652(14) 1.1261(3) 0.0444(6) Uani 1 1 d . . . H22A H 0.4897 0.3644 1.1825 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.43067(10) 0.13198(4) 1.17662(9) 0.0645(3) Uani 1 1 d . . . N1 N 0.3347(3) 0.43723(11) 0.5544(2) 0.0449(5) Uani 1 1 d . . . O1 O 0.4152(2) 0.51912(9) 0.72139(18) 0.0424(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0400(14) 0.0412(15) 0.0417(14) 0.0054(11) 0.0082(12) -0.0079(11) C2 0.0451(15) 0.0470(16) 0.0481(16) -0.0087(12) 0.0149(13) -0.0123(12) C3 0.0378(14) 0.0443(15) 0.0412(14) 0.0040(12) 0.0109(11) 0.0001(12) C4 0.0429(15) 0.0415(15) 0.0408(14) 0.0043(11) 0.0118(12) 0.0005(11) C5 0.0445(15) 0.0469(16) 0.0499(16) -0.0116(12) 0.0150(13) 0.0034(12) C6 0.0417(14) 0.0382(14) 0.0458(15) 0.0079(12) 0.0119(12) 0.0001(11) C7 0.0492(16) 0.0379(13) 0.0463(14) 0.0010(12) 0.0165(12) -0.0172(12) C8 0.0443(14) 0.0361(13) 0.0424(14) -0.0014(11) 0.0128(11) 0.0006(11) C9 0.0399(14) 0.0323(13) 0.0413(14) -0.0031(11) 0.0102(11) 0.0011(10) C10 0.0387(14) 0.0357(13) 0.0438(14) -0.0040(11) 0.0151(11) -0.0019(11) C11 0.0446(14) 0.0356(14) 0.0457(14) -0.0034(11) 0.0198(12) -0.0047(11) C12 0.0412(14) 0.0455(15) 0.0437(14) 0.0020(12) 0.0122(12) 0.0019(11) C13 0.0423(15) 0.0471(15) 0.0398(15) 0.0026(12) 0.0129(12) 0.0104(12) C14 0.0433(14) 0.0423(15) 0.0400(14) 0.0000(11) 0.0138(12) 0.0094(11) C15 0.0395(14) 0.0365(14) 0.0387(14) -0.0033(11) 0.0098(11) 0.0018(11) C16 0.0444(14) 0.0327(13) 0.0427(15) -0.0022(11) 0.0179(11) 0.0007(11) C17 0.0495(15) 0.0338(13) 0.0388(13) -0.0034(11) 0.0092(12) 0.0002(11) C18 0.0439(14) 0.0331(13) 0.0425(14) -0.0051(11) 0.0142(12) -0.0024(11) C19 0.0553(17) 0.0332(13) 0.0447(15) -0.0013(11) 0.0132(13) -0.0018(12) C20 0.0435(15) 0.0427(15) 0.0442(14) 0.0059(12) 0.0099(12) 0.0028(12) C21 0.0410(14) 0.0517(16) 0.0402(14) 0.0019(12) 0.0149(12) 0.0020(12) C22 0.0448(14) 0.0428(15) 0.0405(14) -0.0035(12) 0.0122(12) 0.0050(12) Cl1 0.0626(5) 0.0578(5) 0.0616(5) 0.0169(4) 0.0136(4) -0.0047(4) N1 0.0465(13) 0.0374(12) 0.0430(12) -0.0013(10) 0.0103(10) -0.0032(10) O1 0.0440(10) 0.0393(10) 0.0402(9) -0.0059(8) 0.0134(8) -0.0071(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.348(4) . ? C1 C6 1.377(4) . ? C1 H1A 0.9300 . ? C2 C3 1.379(4) . ? C2 H2A 0.9300 . ? C3 C4 1.370(4) . ? C3 H3A 0.9300 . ? C4 C5 1.384(4) . ? C4 C7 1.505(4) . ? C5 C6 1.374(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 N1 1.441(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.485(3) . ? C8 C12 1.518(4) . ? C8 C9 1.520(4) . ? C8 H8A 0.9800 . ? C9 C10 1.508(3) . ? C9 C15 1.517(3) . ? C9 H9A 0.9800 . ? C10 C18 1.487(4) . ? C10 C11 1.506(4) . ? C10 H10A 0.9800 . ? C11 O1 1.230(3) . ? C11 N1 1.345(3) . ? C12 C13 1.541(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.529(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.539(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.524(3) . ? C15 H15A 0.9800 . ? C16 C19 1.393(4) . ? C16 C17 1.400(4) . ? C17 C22 1.376(4) . ? C17 C18 1.521(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.376(4) . ? C19 H19A 0.9300 . ? C20 C21 1.360(4) . ? C20 Cl1 1.745(3) . ? C21 C22 1.389(4) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.2(3) . . ? C2 C1 H1A 119.9 . . ? C6 C1 H1A 119.9 . . ? C1 C2 C3 121.2(3) . . ? C1 C2 H2A 119.4 . . ? C3 C2 H2A 119.4 . . ? C4 C3 C2 119.5(3) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C3 C4 C5 119.2(2) . . ? C3 C4 C7 119.0(2) . . ? C5 C4 C7 121.8(2) . . ? C6 C5 C4 120.7(3) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C1 119.2(3) . . ? C5 C6 H6A 120.4 . . ? C1 C6 H6A 120.4 . . ? N1 C7 C4 113.1(2) . . ? N1 C7 H7A 109.0 . . ? C4 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C4 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N1 C8 C12 112.1(2) . . ? N1 C8 C9 99.8(2) . . ? C12 C8 C9 113.9(2) . . ? N1 C8 H8A 110.2 . . ? C12 C8 H8A 110.2 . . ? C9 C8 H8A 110.2 . . ? C10 C9 C15 112.2(2) . . ? C10 C9 C8 102.5(2) . . ? C15 C9 C8 117.5(2) . . ? C10 C9 H9A 108.1 . . ? C15 C9 H9A 108.1 . . ? C8 C9 H9A 108.1 . . ? C18 C10 C11 121.2(2) . . ? C18 C10 C9 112.0(2) . . ? C11 C10 C9 102.5(2) . . ? C18 C10 H10A 106.8 . . ? C11 C10 H10A 106.8 . . ? C9 C10 H10A 106.8 . . ? O1 C11 N1 124.7(2) . . ? O1 C11 C10 127.9(2) . . ? N1 C11 C10 107.4(2) . . ? C8 C12 C13 110.6(2) . . ? C8 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C14 C13 C12 110.1(2) . . ? C14 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? C14 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.2 . . ? C13 C14 C15 111.1(2) . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14B 109.4 . . ? C15 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C9 C15 C16 109.3(2) . . ? C9 C15 C14 112.2(2) . . ? C16 C15 C14 112.8(2) . . ? C9 C15 H15A 107.4 . . ? C16 C15 H15A 107.4 . . ? C14 C15 H15A 107.4 . . ? C19 C16 C17 119.2(2) . . ? C19 C16 C15 118.2(2) . . ? C17 C16 C15 122.6(2) . . ? C22 C17 C16 118.8(3) . . ? C22 C17 C18 119.0(2) . . ? C16 C17 C18 122.2(2) . . ? C10 C18 C17 111.2(2) . . ? C10 C18 H18A 109.4 . . ? C17 C18 H18A 109.4 . . ? C10 C18 H18B 109.4 . . ? C17 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C20 C19 C16 120.0(3) . . ? C20 C19 H19A 120.0 . . ? C16 C19 H19A 120.0 . . ? C21 C20 C19 121.5(3) . . ? C21 C20 Cl1 119.3(2) . . ? C19 C20 Cl1 119.2(2) . . ? C20 C21 C22 118.6(3) . . ? C20 C21 H21A 120.7 . . ? C22 C21 H21A 120.7 . . ? C17 C22 C21 121.7(3) . . ? C17 C22 H22A 119.1 . . ? C21 C22 H22A 119.1 . . ? C11 N1 C7 124.5(2) . . ? C11 N1 C8 112.3(2) . . ? C7 N1 C8 122.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.4(4) . . . . ? C1 C2 C3 C4 1.1(4) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C2 C3 C4 C7 179.4(3) . . . . ? C3 C4 C5 C6 -0.8(4) . . . . ? C7 C4 C5 C6 179.3(3) . . . . ? C4 C5 C6 C1 1.5(4) . . . . ? C2 C1 C6 C5 -0.9(4) . . . . ? C3 C4 C7 N1 -122.0(3) . . . . ? C5 C4 C7 N1 57.9(4) . . . . ? N1 C8 C9 C10 -37.2(2) . . . . ? C12 C8 C9 C10 82.4(3) . . . . ? N1 C8 C9 C15 -160.6(2) . . . . ? C12 C8 C9 C15 -41.0(3) . . . . ? C15 C9 C10 C18 -65.2(3) . . . . ? C8 C9 C10 C18 167.9(2) . . . . ? C15 C9 C10 C11 163.4(2) . . . . ? C8 C9 C10 C11 36.5(2) . . . . ? C18 C10 C11 O1 35.2(4) . . . . ? C9 C10 C11 O1 160.8(3) . . . . ? C18 C10 C11 N1 -147.1(2) . . . . ? C9 C10 C11 N1 -21.5(3) . . . . ? N1 C8 C12 C13 161.7(2) . . . . ? C9 C8 C12 C13 49.2(3) . . . . ? C8 C12 C13 C14 -59.8(3) . . . . ? C12 C13 C14 C15 60.7(3) . . . . ? C10 C9 C15 C16 48.4(3) . . . . ? C8 C9 C15 C16 166.8(2) . . . . ? C10 C9 C15 C14 -77.5(3) . . . . ? C8 C9 C15 C14 40.9(3) . . . . ? C13 C14 C15 C9 -50.3(3) . . . . ? C13 C14 C15 C16 -174.2(2) . . . . ? C9 C15 C16 C19 158.8(2) . . . . ? C14 C15 C16 C19 -75.6(3) . . . . ? C9 C15 C16 C17 -19.9(3) . . . . ? C14 C15 C16 C17 105.7(3) . . . . ? C19 C16 C17 C22 5.7(4) . . . . ? C15 C16 C17 C22 -175.6(3) . . . . ? C19 C16 C17 C18 -173.6(3) . . . . ? C15 C16 C17 C18 5.1(4) . . . . ? C11 C10 C18 C17 167.5(2) . . . . ? C9 C10 C18 C17 46.3(3) . . . . ? C22 C17 C18 C10 162.9(2) . . . . ? C16 C17 C18 C10 -17.8(4) . . . . ? C17 C16 C19 C20 -3.6(4) . . . . ? C15 C16 C19 C20 177.7(3) . . . . ? C16 C19 C20 C21 -0.1(5) . . . . ? C16 C19 C20 Cl1 178.9(2) . . . . ? C19 C20 C21 C22 1.5(4) . . . . ? Cl1 C20 C21 C22 -177.5(2) . . . . ? C16 C17 C22 C21 -4.3(4) . . . . ? C18 C17 C22 C21 175.0(2) . . . . ? C20 C21 C22 C17 0.7(4) . . . . ? O1 C11 N1 C7 6.5(4) . . . . ? C10 C11 N1 C7 -171.3(2) . . . . ? O1 C11 N1 C8 174.9(2) . . . . ? C10 C11 N1 C8 -3.0(3) . . . . ? C4 C7 N1 C11 -143.6(3) . . . . ? C4 C7 N1 C8 49.2(4) . . . . ? C12 C8 N1 C11 -95.2(3) . . . . ? C9 C8 N1 C11 25.7(3) . . . . ? C12 C8 N1 C7 73.5(3) . . . . ? C9 C8 N1 C7 -165.6(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.27 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.181 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.045 ##################END