# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Zhang, Junliang' _publ_contact_author_email jlzhang@chem.ecnu.edu.cn _publ_section_title ; Product-Selectivity Control by the Nature of Catalyst: Lewis Acid-Catalyzed Selective Formations of Ring-fused Tetrahydroquinolines and Tetrahydroazepines via Intramolecular Redox Reaction ; loop_ _publ_author_name 'Junliang Zhang' 'Guanghua Zhou' # Attachment '- 2n.cif' data_2n _database_code_depnum_ccdc_archive 'CCDC 772731' #TrackingRef '- 2n.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H40 Br2 N2 O4' _chemical_formula_weight 820.60 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5738(8) _cell_length_b 10.0161(8) _cell_length_c 20.1161(16) _cell_angle_alpha 93.144(2) _cell_angle_beta 92.573(2) _cell_angle_gamma 107.028(2) _cell_volume 1837.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 2.253 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5419 _exptl_absorpt_correction_T_max 0.5814 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21034 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6398 _reflns_number_gt 5382 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+2.6897P] 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 6398 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N -0.6265(3) -0.2260(3) 0.07216(13) 0.0276(6) Uani 1 1 d . . . Br2 Br -0.35354(4) 0.17298(4) 0.254150(18) 0.04310(12) Uani 1 1 d . . . N1 N -0.1188(3) -0.2642(3) 0.41452(13) 0.0262(6) Uani 1 1 d . . . Br1 Br 0.20524(4) 0.10808(3) 0.266275(17) 0.03351(11) Uani 1 1 d . . . O1 O -0.1829(2) -0.5390(2) 0.45915(13) 0.0376(6) Uani 1 1 d . . . O2 O -0.3578(3) -0.3168(3) 0.58564(12) 0.0390(6) Uani 1 1 d . . . O3 O -0.6876(2) -0.5107(2) 0.02609(11) 0.0314(5) Uani 1 1 d . . . O4 O -0.8581(3) -0.3092(3) -0.11360(12) 0.0406(6) Uani 1 1 d . . . C1 C -0.1004(3) 0.1071(3) 0.40484(16) 0.0257(7) Uani 1 1 d . . . H1A H -0.1467 0.1714 0.4231 0.031 Uiso 1 1 calc R . . C2 C 0.0004(3) 0.1506(3) 0.35729(16) 0.0288(7) Uani 1 1 d . . . H2A H 0.0240 0.2430 0.3430 0.035 Uiso 1 1 calc R . . C3 C 0.0649(3) 0.0549(3) 0.33167(15) 0.0253(6) Uani 1 1 d . . . C4 C 0.0298(3) -0.0812(3) 0.35060(15) 0.0246(6) Uani 1 1 d . . . H4A H 0.0760 -0.1449 0.3315 0.029 Uiso 1 1 calc R . . C5 C -0.0741(3) -0.1250(3) 0.39820(15) 0.0226(6) Uani 1 1 d . . . C6 C -0.1361(3) -0.0265(3) 0.42669(15) 0.0225(6) Uani 1 1 d . . . C7 C -0.2360(3) -0.0633(3) 0.48283(16) 0.0253(6) Uani 1 1 d . . . H7A H -0.3066 -0.0082 0.4813 0.030 Uiso 1 1 calc R . . H7B H -0.1774 -0.0374 0.5259 0.030 Uiso 1 1 calc R . . C8 C -0.3206(3) -0.2201(3) 0.47897(15) 0.0218(6) Uani 1 1 d . . . C9 C -0.2099(3) -0.3044(3) 0.47140(15) 0.0234(6) Uani 1 1 d . . . H9A H -0.1440 -0.2857 0.5130 0.028 Uiso 1 1 calc R . . C10 C -0.2865(4) -0.4617(3) 0.46184(18) 0.0316(7) Uani 1 1 d . . . H10A H -0.3498 -0.4911 0.4992 0.038 Uiso 1 1 calc R . . H10B H -0.3496 -0.4825 0.4199 0.038 Uiso 1 1 calc R . . C11 C -0.0968(4) -0.5016(4) 0.4038(2) 0.0429(9) Uani 1 1 d . . . H11A H -0.1608 -0.5265 0.3622 0.051 Uiso 1 1 calc R . . H11B H -0.0250 -0.5553 0.4019 0.051 Uiso 1 1 calc R . . C12 C -0.0165(4) -0.3470(4) 0.4082(2) 0.0402(9) Uani 1 1 d . . . H12A H 0.0551 -0.3236 0.4473 0.048 Uiso 1 1 calc R . . H12B H 0.0381 -0.3235 0.3677 0.048 Uiso 1 1 calc R . . C13 C -0.4358(3) -0.2558(3) 0.42372(15) 0.0237(6) Uani 1 1 d . . . C14 C -0.5330(3) -0.2865(3) 0.38113(15) 0.0261(7) Uani 1 1 d . . . C15 C -0.6452(3) -0.3272(3) 0.32713(15) 0.0236(6) Uani 1 1 d . . . C16 C -0.7219(4) -0.4673(3) 0.31279(17) 0.0329(7) Uani 1 1 d . . . H16A H -0.7018 -0.5365 0.3389 0.039 Uiso 1 1 calc R . . C17 C -0.8277(4) -0.5060(4) 0.26051(18) 0.0383(8) Uani 1 1 d . . . H17A H -0.8820 -0.6017 0.2515 0.046 Uiso 1 1 calc R . . C18 C -0.8546(3) -0.4058(4) 0.22136(16) 0.0306(7) Uani 1 1 d . . . H18A H -0.9264 -0.4330 0.1851 0.037 Uiso 1 1 calc R . . C19 C -0.7773(4) -0.2664(3) 0.23496(16) 0.0308(7) Uani 1 1 d . . . H19A H -0.7960 -0.1978 0.2081 0.037 Uiso 1 1 calc R . . C20 C -0.6730(3) -0.2268(3) 0.28754(16) 0.0280(7) Uani 1 1 d . . . H20A H -0.6199 -0.1309 0.2968 0.034 Uiso 1 1 calc R . . C21 C -0.3953(3) -0.2471(3) 0.54583(16) 0.0268(7) Uani 1 1 d . . . C22 C -0.5101(4) -0.1765(4) 0.56003(18) 0.0363(8) Uani 1 1 d . . . H22A H -0.5489 -0.2020 0.6034 0.054 Uiso 1 1 calc R . . H22B H -0.5897 -0.2067 0.5251 0.054 Uiso 1 1 calc R . . H22C H -0.4668 -0.0748 0.5610 0.054 Uiso 1 1 calc R . . C23 C -0.6194(3) 0.1452(3) 0.08387(16) 0.0291(7) Uani 1 1 d . . . H23A H -0.6609 0.2058 0.0605 0.035 Uiso 1 1 calc R . . C24 C -0.5318(3) 0.1982(3) 0.14151(17) 0.0312(7) Uani 1 1 d . . . H24A H -0.5120 0.2932 0.1577 0.037 Uiso 1 1 calc R . . C25 C -0.4746(3) 0.1068(3) 0.17437(16) 0.0290(7) Uani 1 1 d . . . C26 C -0.5028(3) -0.0319(3) 0.15204(16) 0.0278(7) Uani 1 1 d . . . H26A H -0.4620 -0.0916 0.1764 0.033 Uiso 1 1 calc R . . C27 C -0.5912(3) -0.0847(3) 0.09361(15) 0.0239(6) Uani 1 1 d . . . C28 C -0.6490(3) 0.0076(3) 0.05877(15) 0.0252(7) Uani 1 1 d . . . C29 C -0.7418(3) -0.0449(3) -0.00510(15) 0.0263(7) Uani 1 1 d . . . H29A H -0.6782 -0.0345 -0.0431 0.032 Uiso 1 1 calc R . . H29B H -0.8095 0.0119 -0.0120 0.032 Uiso 1 1 calc R . . C30 C -0.8311(3) -0.2010(3) -0.00262(15) 0.0233(6) Uani 1 1 d . . . C31 C -0.7200(3) -0.2822(3) 0.01142(15) 0.0236(6) Uani 1 1 d . . . H31A H -0.6561 -0.2743 -0.0270 0.028 Uiso 1 1 calc R . . C32 C -0.7932(3) -0.4370(3) 0.01944(16) 0.0273(7) Uani 1 1 d . . . H32A H -0.8511 -0.4471 0.0594 0.033 Uiso 1 1 calc R . . H32B H -0.8611 -0.4781 -0.0199 0.033 Uiso 1 1 calc R . . C33 C -0.5936(4) -0.4569(3) 0.08427(17) 0.0324(7) Uani 1 1 d . . . H33A H -0.5186 -0.5068 0.0877 0.039 Uiso 1 1 calc R . . H33B H -0.6515 -0.4740 0.1242 0.039 Uiso 1 1 calc R . . C34 C -0.5187(4) -0.3015(3) 0.08273(17) 0.0311(7) Uani 1 1 d . . . H34A H -0.4609 -0.2657 0.1254 0.037 Uiso 1 1 calc R . . H34B H -0.4506 -0.2851 0.0464 0.037 Uiso 1 1 calc R . . C35 C -0.9383(3) -0.2165(3) 0.04936(15) 0.0239(6) Uani 1 1 d . . . C36 C -1.0257(3) -0.2303(3) 0.09052(16) 0.0270(7) Uani 1 1 d . . . C37 C -1.1250(3) -0.2531(3) 0.14351(15) 0.0242(6) Uani 1 1 d . . . C38 C -1.1990(3) -0.3885(4) 0.15880(16) 0.0306(7) Uani 1 1 d . . . H38A H -1.1910 -0.4664 0.1318 0.037 Uiso 1 1 calc R . . C39 C -1.2840(4) -0.4098(4) 0.21297(17) 0.0391(8) Uani 1 1 d . . . H39A H -1.3318 -0.5026 0.2238 0.047 Uiso 1 1 calc R . . C40 C -1.3002(4) -0.2985(4) 0.25140(17) 0.0389(9) Uani 1 1 d . . . H40A H -1.3592 -0.3142 0.2886 0.047 Uiso 1 1 calc R . . C41 C -1.2310(4) -0.1639(4) 0.23596(17) 0.0390(9) Uani 1 1 d . . . H41A H -1.2431 -0.0869 0.2623 0.047 Uiso 1 1 calc R . . C42 C -1.1435(3) -0.1401(4) 0.18208(16) 0.0315(7) Uani 1 1 d . . . H42A H -1.0963 -0.0471 0.1715 0.038 Uiso 1 1 calc R . . C43 C -0.9096(3) -0.2484(3) -0.07270(15) 0.0259(7) Uani 1 1 d . . . C44 C -1.0478(4) -0.2124(4) -0.08735(17) 0.0346(8) Uani 1 1 d . . . H44A H -1.0867 -0.2481 -0.1329 0.052 Uiso 1 1 calc R . . H44B H -1.0278 -0.1104 -0.0831 0.052 Uiso 1 1 calc R . . H44C H -1.1198 -0.2549 -0.0557 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N2 0.0273(14) 0.0277(14) 0.0280(15) 0.0007(11) -0.0045(11) 0.0098(11) Br2 0.0502(2) 0.0396(2) 0.0325(2) -0.00476(15) -0.01185(16) 0.00589(16) N1 0.0260(13) 0.0218(13) 0.0328(15) 0.0083(11) 0.0080(11) 0.0082(11) Br1 0.03365(19) 0.03072(18) 0.0351(2) 0.00747(14) 0.01249(14) 0.00551(14) O1 0.0337(13) 0.0290(12) 0.0550(16) 0.0158(11) 0.0103(11) 0.0136(10) O2 0.0405(14) 0.0493(15) 0.0294(13) 0.0175(11) 0.0040(11) 0.0138(12) O3 0.0283(12) 0.0294(11) 0.0374(13) -0.0003(10) -0.0034(10) 0.0112(10) O4 0.0425(14) 0.0554(16) 0.0272(13) -0.0048(11) -0.0004(11) 0.0214(12) C1 0.0212(15) 0.0215(15) 0.0336(18) 0.0010(13) -0.0004(13) 0.0054(12) C2 0.0293(17) 0.0232(15) 0.0329(18) 0.0044(13) 0.0040(14) 0.0054(13) C3 0.0215(15) 0.0280(16) 0.0235(16) 0.0042(13) 0.0024(12) 0.0022(12) C4 0.0237(15) 0.0251(15) 0.0248(17) 0.0007(13) 0.0013(12) 0.0072(12) C5 0.0200(15) 0.0228(15) 0.0233(16) 0.0031(12) -0.0037(12) 0.0042(12) C6 0.0134(13) 0.0273(15) 0.0250(16) 0.0008(12) -0.0013(11) 0.0040(12) C7 0.0224(15) 0.0243(15) 0.0284(17) 0.0016(13) 0.0008(13) 0.0059(12) C8 0.0184(14) 0.0240(15) 0.0217(16) 0.0032(12) -0.0008(12) 0.0043(12) C9 0.0179(14) 0.0253(15) 0.0257(17) 0.0055(12) -0.0015(12) 0.0040(12) C10 0.0290(17) 0.0242(16) 0.042(2) 0.0073(14) 0.0037(14) 0.0073(13) C11 0.053(2) 0.0284(18) 0.052(2) 0.0065(16) 0.0168(19) 0.0173(17) C12 0.0363(19) 0.0324(18) 0.058(2) 0.0112(17) 0.0187(17) 0.0160(15) C13 0.0219(15) 0.0283(16) 0.0224(16) 0.0067(13) 0.0045(13) 0.0083(12) C14 0.0234(16) 0.0324(16) 0.0247(17) 0.0057(13) 0.0049(13) 0.0105(13) C15 0.0184(15) 0.0343(16) 0.0206(16) 0.0051(13) 0.0030(12) 0.0111(13) C16 0.0366(18) 0.0320(17) 0.0309(19) 0.0110(14) -0.0041(14) 0.0107(15) C17 0.042(2) 0.0318(18) 0.037(2) 0.0029(15) -0.0057(16) 0.0049(15) C18 0.0262(16) 0.0434(19) 0.0236(17) 0.0019(14) -0.0060(13) 0.0135(14) C19 0.0317(17) 0.0366(18) 0.0288(18) 0.0075(14) -0.0011(14) 0.0170(14) C20 0.0252(16) 0.0297(16) 0.0288(18) 0.0025(13) 0.0008(13) 0.0076(13) C21 0.0234(16) 0.0265(16) 0.0257(17) 0.0026(13) -0.0003(13) 0.0000(13) C22 0.0368(19) 0.042(2) 0.033(2) 0.0042(16) 0.0131(15) 0.0143(16) C23 0.0210(16) 0.0302(17) 0.0351(19) 0.0075(14) 0.0014(13) 0.0053(13) C24 0.0286(17) 0.0264(16) 0.0351(19) 0.0020(14) 0.0028(14) 0.0030(13) C25 0.0281(17) 0.0329(17) 0.0211(16) 0.0018(13) 0.0016(13) 0.0014(14) C26 0.0267(16) 0.0298(16) 0.0266(17) 0.0073(13) 0.0022(13) 0.0068(13) C27 0.0165(14) 0.0276(16) 0.0264(17) 0.0060(13) 0.0041(12) 0.0036(12) C28 0.0167(14) 0.0312(16) 0.0260(17) 0.0043(13) 0.0035(12) 0.0038(12) C29 0.0233(16) 0.0298(16) 0.0246(17) 0.0077(13) 0.0024(13) 0.0048(13) C30 0.0152(14) 0.0315(16) 0.0223(16) 0.0027(13) 0.0015(12) 0.0050(12) C31 0.0194(15) 0.0301(16) 0.0217(16) 0.0029(12) 0.0020(12) 0.0077(12) C32 0.0212(15) 0.0305(16) 0.0297(17) -0.0001(13) 0.0016(13) 0.0072(13) C33 0.0300(17) 0.0339(18) 0.0341(19) 0.0003(14) -0.0049(14) 0.0119(14) C34 0.0278(17) 0.0322(17) 0.0328(19) 0.0027(14) -0.0053(14) 0.0094(14) C35 0.0172(14) 0.0278(15) 0.0248(17) 0.0011(13) -0.0028(13) 0.0044(12) C36 0.0240(16) 0.0318(16) 0.0248(17) 0.0015(13) -0.0023(13) 0.0084(13) C37 0.0167(14) 0.0347(17) 0.0214(16) 0.0025(13) -0.0002(12) 0.0081(13) C38 0.0232(16) 0.0384(18) 0.0301(18) -0.0028(14) -0.0014(13) 0.0102(14) C39 0.0291(18) 0.053(2) 0.030(2) 0.0089(17) 0.0026(15) 0.0042(16) C40 0.0286(18) 0.068(3) 0.0195(18) 0.0045(17) 0.0063(14) 0.0120(17) C41 0.0308(18) 0.064(2) 0.0272(18) -0.0149(17) -0.0060(14) 0.0252(18) C42 0.0280(17) 0.0366(18) 0.0291(18) -0.0037(14) -0.0048(14) 0.0104(14) C43 0.0238(16) 0.0268(15) 0.0240(17) 0.0063(13) 0.0001(13) 0.0020(13) C44 0.0282(17) 0.0429(19) 0.0329(19) 0.0036(15) -0.0055(14) 0.0117(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C27 1.394(4) . ? N2 C34 1.462(4) . ? N2 C31 1.464(4) . ? Br2 C25 1.904(3) . ? N1 C5 1.396(4) . ? N1 C12 1.463(4) . ? N1 C9 1.472(4) . ? Br1 C3 1.907(3) . ? O1 C11 1.417(4) . ? O1 C10 1.428(4) . ? O2 C21 1.200(4) . ? O3 C32 1.422(4) . ? O3 C33 1.422(4) . ? O4 C43 1.203(4) . ? C1 C6 1.382(4) . ? C1 C2 1.385(4) . ? C1 H1A 0.9500 . ? C2 C3 1.373(4) . ? C2 H2A 0.9500 . ? C3 C4 1.385(4) . ? C4 C5 1.405(4) . ? C4 H4A 0.9500 . ? C5 C6 1.402(4) . ? C6 C7 1.504(4) . ? C7 C8 1.538(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.481(4) . ? C8 C9 1.545(4) . ? C8 C21 1.551(4) . ? C9 C10 1.528(4) . ? C9 H9A 1.0000 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.509(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.194(4) . ? C14 C15 1.446(4) . ? C15 C16 1.387(4) . ? C15 C20 1.393(4) . ? C16 C17 1.382(5) . ? C16 H16A 0.9500 . ? C17 C18 1.383(5) . ? C17 H17A 0.9500 . ? C18 C19 1.381(5) . ? C18 H18A 0.9500 . ? C19 C20 1.379(4) . ? C19 H19A 0.9500 . ? C20 H20A 0.9500 . ? C21 C22 1.500(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.383(5) . ? C23 C28 1.385(4) . ? C23 H23A 0.9500 . ? C24 C25 1.380(5) . ? C24 H24A 0.9500 . ? C25 C26 1.380(4) . ? C26 C27 1.399(4) . ? C26 H26A 0.9500 . ? C27 C28 1.409(4) . ? C28 C29 1.505(4) . ? C29 C30 1.552(4) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C35 1.481(4) . ? C30 C31 1.542(4) . ? C30 C43 1.549(4) . ? C31 C32 1.524(4) . ? C31 H31A 1.0000 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.514(4) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.188(4) . ? C36 C37 1.443(4) . ? C37 C38 1.392(5) . ? C37 C42 1.396(4) . ? C38 C39 1.378(5) . ? C38 H38A 0.9500 . ? C39 C40 1.372(5) . ? C39 H39A 0.9500 . ? C40 C41 1.376(5) . ? C40 H40A 0.9500 . ? C41 C42 1.388(5) . ? C41 H41A 0.9500 . ? C42 H42A 0.9500 . ? C43 C44 1.492(4) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C27 N2 C34 119.5(2) . . ? C27 N2 C31 121.1(2) . . ? C34 N2 C31 111.0(2) . . ? C5 N1 C12 118.7(2) . . ? C5 N1 C9 120.2(2) . . ? C12 N1 C9 110.9(2) . . ? C11 O1 C10 109.4(2) . . ? C32 O3 C33 109.9(2) . . ? C6 C1 C2 122.4(3) . . ? C6 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C3 C2 C1 117.3(3) . . ? C3 C2 H2A 121.3 . . ? C1 C2 H2A 121.3 . . ? C2 C3 C4 122.4(3) . . ? C2 C3 Br1 119.6(2) . . ? C4 C3 Br1 118.0(2) . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? N1 C5 C6 120.9(3) . . ? N1 C5 C4 120.8(3) . . ? C6 C5 C4 118.2(3) . . ? C1 C6 C5 119.7(3) . . ? C1 C6 C7 119.8(3) . . ? C5 C6 C7 120.5(3) . . ? C6 C7 C8 112.1(2) . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C13 C8 C7 110.8(2) . . ? C13 C8 C9 112.3(2) . . ? C7 C8 C9 108.4(2) . . ? C13 C8 C21 108.6(2) . . ? C7 C8 C21 106.2(2) . . ? C9 C8 C21 110.4(2) . . ? N1 C9 C10 107.9(3) . . ? N1 C9 C8 112.2(2) . . ? C10 C9 C8 111.7(2) . . ? N1 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9A 108.3 . . ? O1 C10 C9 111.2(3) . . ? O1 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? O1 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? O1 C11 C12 111.5(3) . . ? O1 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? O1 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? N1 C12 C11 110.8(3) . . ? N1 C12 H12A 109.5 . . ? C11 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C14 C13 C8 177.2(3) . . ? C13 C14 C15 176.6(3) . . ? C16 C15 C20 119.6(3) . . ? C16 C15 C14 120.1(3) . . ? C20 C15 C14 120.3(3) . . ? C17 C16 C15 119.9(3) . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C16 C17 C18 120.2(3) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? C19 C18 C17 120.1(3) . . ? C19 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? C20 C19 C18 120.1(3) . . ? C20 C19 H19A 120.0 . . ? C18 C19 H19A 120.0 . . ? C19 C20 C15 120.2(3) . . ? C19 C20 H20A 119.9 . . ? C15 C20 H20A 119.9 . . ? O2 C21 C22 121.6(3) . . ? O2 C21 C8 121.0(3) . . ? C22 C21 C8 117.3(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 122.8(3) . . ? C24 C23 H23A 118.6 . . ? C28 C23 H23A 118.6 . . ? C25 C24 C23 117.0(3) . . ? C25 C24 H24A 121.5 . . ? C23 C24 H24A 121.5 . . ? C24 C25 C26 122.5(3) . . ? C24 C25 Br2 119.1(2) . . ? C26 C25 Br2 118.4(2) . . ? C25 C26 C27 120.2(3) . . ? C25 C26 H26A 119.9 . . ? C27 C26 H26A 119.9 . . ? N2 C27 C26 120.8(3) . . ? N2 C27 C28 120.9(3) . . ? C26 C27 C28 118.2(3) . . ? C23 C28 C27 119.4(3) . . ? C23 C28 C29 121.0(3) . . ? C27 C28 C29 119.6(3) . . ? C28 C29 C30 110.6(2) . . ? C28 C29 H29A 109.5 . . ? C30 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 108.1 . . ? C35 C30 C31 112.0(2) . . ? C35 C30 C43 111.0(2) . . ? C31 C30 C43 110.1(2) . . ? C35 C30 C29 110.3(2) . . ? C31 C30 C29 106.9(2) . . ? C43 C30 C29 106.4(2) . . ? N2 C31 C32 106.9(2) . . ? N2 C31 C30 112.2(2) . . ? C32 C31 C30 112.8(2) . . ? N2 C31 H31A 108.2 . . ? C32 C31 H31A 108.2 . . ? C30 C31 H31A 108.2 . . ? O3 C32 C31 111.1(2) . . ? O3 C32 H32A 109.4 . . ? C31 C32 H32A 109.4 . . ? O3 C32 H32B 109.4 . . ? C31 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? O3 C33 C34 111.5(3) . . ? O3 C33 H33A 109.3 . . ? C34 C33 H33A 109.3 . . ? O3 C33 H33B 109.3 . . ? C34 C33 H33B 109.3 . . ? H33A C33 H33B 108.0 . . ? N2 C34 C33 110.6(3) . . ? N2 C34 H34A 109.5 . . ? C33 C34 H34A 109.5 . . ? N2 C34 H34B 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 108.1 . . ? C36 C35 C30 179.1(3) . . ? C35 C36 C37 175.4(3) . . ? C38 C37 C42 118.9(3) . . ? C38 C37 C36 120.4(3) . . ? C42 C37 C36 120.6(3) . . ? C39 C38 C37 120.2(3) . . ? C39 C38 H38A 119.9 . . ? C37 C38 H38A 119.9 . . ? C40 C39 C38 120.7(3) . . ? C40 C39 H39A 119.7 . . ? C38 C39 H39A 119.7 . . ? C39 C40 C41 119.9(3) . . ? C39 C40 H40A 120.0 . . ? C41 C40 H40A 120.0 . . ? C40 C41 C42 120.3(3) . . ? C40 C41 H41A 119.8 . . ? C42 C41 H41A 119.8 . . ? C41 C42 C37 119.9(3) . . ? C41 C42 H42A 120.1 . . ? C37 C42 H42A 120.1 . . ? O4 C43 C44 122.1(3) . . ? O4 C43 C30 120.6(3) . . ? C44 C43 C30 117.3(3) . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.3(5) . . . . ? C1 C2 C3 C4 1.5(5) . . . . ? C1 C2 C3 Br1 -179.7(2) . . . . ? C2 C3 C4 C5 -0.7(5) . . . . ? Br1 C3 C4 C5 -179.4(2) . . . . ? C12 N1 C5 C6 -154.2(3) . . . . ? C9 N1 C5 C6 -12.1(4) . . . . ? C12 N1 C5 C4 28.5(4) . . . . ? C9 N1 C5 C4 170.6(3) . . . . ? C3 C4 C5 N1 175.4(3) . . . . ? C3 C4 C5 C6 -2.0(4) . . . . ? C2 C1 C6 C5 -2.9(5) . . . . ? C2 C1 C6 C7 174.5(3) . . . . ? N1 C5 C6 C1 -173.7(3) . . . . ? C4 C5 C6 C1 3.7(4) . . . . ? N1 C5 C6 C7 8.9(4) . . . . ? C4 C5 C6 C7 -173.7(3) . . . . ? C1 C6 C7 C8 152.7(3) . . . . ? C5 C6 C7 C8 -29.9(4) . . . . ? C6 C7 C8 C13 -72.6(3) . . . . ? C6 C7 C8 C9 51.0(3) . . . . ? C6 C7 C8 C21 169.7(2) . . . . ? C5 N1 C9 C10 159.4(3) . . . . ? C12 N1 C9 C10 -55.9(3) . . . . ? C5 N1 C9 C8 35.9(4) . . . . ? C12 N1 C9 C8 -179.3(3) . . . . ? C13 C8 C9 N1 68.3(3) . . . . ? C7 C8 C9 N1 -54.4(3) . . . . ? C21 C8 C9 N1 -170.4(2) . . . . ? C13 C8 C9 C10 -52.9(3) . . . . ? C7 C8 C9 C10 -175.6(3) . . . . ? C21 C8 C9 C10 68.4(3) . . . . ? C11 O1 C10 C9 -61.7(4) . . . . ? N1 C9 C10 O1 59.9(3) . . . . ? C8 C9 C10 O1 -176.3(3) . . . . ? C10 O1 C11 C12 59.0(4) . . . . ? C5 N1 C12 C11 -159.9(3) . . . . ? C9 N1 C12 C11 54.8(4) . . . . ? O1 C11 C12 N1 -56.0(4) . . . . ? C7 C8 C13 C14 -120(6) . . . . ? C9 C8 C13 C14 118(6) . . . . ? C21 C8 C13 C14 -4(7) . . . . ? C8 C13 C14 C15 -138(6) . . . . ? C13 C14 C15 C16 72(6) . . . . ? C13 C14 C15 C20 -105(6) . . . . ? C20 C15 C16 C17 -1.6(5) . . . . ? C14 C15 C16 C17 -179.1(3) . . . . ? C15 C16 C17 C18 1.7(5) . . . . ? C16 C17 C18 C19 -0.9(5) . . . . ? C17 C18 C19 C20 0.1(5) . . . . ? C18 C19 C20 C15 0.0(5) . . . . ? C16 C15 C20 C19 0.8(5) . . . . ? C14 C15 C20 C19 178.2(3) . . . . ? C13 C8 C21 O2 128.6(3) . . . . ? C7 C8 C21 O2 -112.2(3) . . . . ? C9 C8 C21 O2 5.1(4) . . . . ? C13 C8 C21 C22 -54.5(3) . . . . ? C7 C8 C21 C22 64.7(3) . . . . ? C9 C8 C21 C22 -178.0(3) . . . . ? C28 C23 C24 C25 -0.6(5) . . . . ? C23 C24 C25 C26 -0.5(5) . . . . ? C23 C24 C25 Br2 -179.9(2) . . . . ? C24 C25 C26 C27 0.7(5) . . . . ? Br2 C25 C26 C27 -180.0(2) . . . . ? C34 N2 C27 C26 -35.2(4) . . . . ? C31 N2 C27 C26 179.4(3) . . . . ? C34 N2 C27 C28 147.7(3) . . . . ? C31 N2 C27 C28 2.4(4) . . . . ? C25 C26 C27 N2 -176.9(3) . . . . ? C25 C26 C27 C28 0.3(4) . . . . ? C24 C23 C28 C27 1.5(5) . . . . ? C24 C23 C28 C29 -178.5(3) . . . . ? N2 C27 C28 C23 175.8(3) . . . . ? C26 C27 C28 C23 -1.3(4) . . . . ? N2 C27 C28 C29 -4.2(4) . . . . ? C26 C27 C28 C29 178.6(3) . . . . ? C23 C28 C29 C30 -147.2(3) . . . . ? C27 C28 C29 C30 32.8(4) . . . . ? C28 C29 C30 C35 65.3(3) . . . . ? C28 C29 C30 C31 -56.7(3) . . . . ? C28 C29 C30 C43 -174.3(2) . . . . ? C27 N2 C31 C32 -153.9(3) . . . . ? C34 N2 C31 C32 58.1(3) . . . . ? C27 N2 C31 C30 -29.7(4) . . . . ? C34 N2 C31 C30 -177.8(2) . . . . ? C35 C30 C31 N2 -65.2(3) . . . . ? C43 C30 C31 N2 170.8(2) . . . . ? C29 C30 C31 N2 55.7(3) . . . . ? C35 C30 C31 C32 55.7(3) . . . . ? C43 C30 C31 C32 -68.3(3) . . . . ? C29 C30 C31 C32 176.5(2) . . . . ? C33 O3 C32 C31 61.8(3) . . . . ? N2 C31 C32 O3 -61.6(3) . . . . ? C30 C31 C32 O3 174.6(2) . . . . ? C32 O3 C33 C34 -57.3(3) . . . . ? C27 N2 C34 C33 155.7(3) . . . . ? C31 N2 C34 C33 -55.7(3) . . . . ? O3 C33 C34 N2 54.4(4) . . . . ? C31 C30 C35 C36 -97(23) . . . . ? C43 C30 C35 C36 27(23) . . . . ? C29 C30 C35 C36 144(23) . . . . ? C30 C35 C36 C37 103(22) . . . . ? C35 C36 C37 C38 -60(4) . . . . ? C35 C36 C37 C42 117(4) . . . . ? C42 C37 C38 C39 -2.8(4) . . . . ? C36 C37 C38 C39 174.5(3) . . . . ? C37 C38 C39 C40 1.9(5) . . . . ? C38 C39 C40 C41 -0.1(5) . . . . ? C39 C40 C41 C42 -0.6(5) . . . . ? C40 C41 C42 C37 -0.3(5) . . . . ? C38 C37 C42 C41 2.0(4) . . . . ? C36 C37 C42 C41 -175.2(3) . . . . ? C35 C30 C43 O4 -142.8(3) . . . . ? C31 C30 C43 O4 -18.3(4) . . . . ? C29 C30 C43 O4 97.2(3) . . . . ? C35 C30 C43 C44 38.7(4) . . . . ? C31 C30 C43 C44 163.2(3) . . . . ? C29 C30 C43 C44 -81.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.562 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.068 # Attachment '- 3g.cif' data_3g _database_code_depnum_ccdc_archive 'CCDC 772732' #TrackingRef '- 3g.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H23 N O' _chemical_formula_weight 329.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.7910(3) _cell_length_b 16.6191(5) _cell_length_c 8.9716(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.6170(10) _cell_angle_gamma 90.00 _cell_volume 1757.34(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.556 _exptl_crystal_size_mid 0.425 _exptl_crystal_size_min 0.318 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.877321 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20031 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0123 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3097 _reflns_number_gt 2802 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.5957P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0047(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3097 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1226 _refine_ls_wR_factor_gt 0.1176 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.15358(9) 0.20093(6) 0.74762(12) 0.0387(3) Uani 1 1 d . . . N1 N 0.35663(10) 0.43768(8) 0.85608(14) 0.0378(3) Uani 1 1 d . . . C1 C 0.57206(13) 0.28029(11) 0.79479(18) 0.0461(4) Uani 1 1 d . . . H1A H 0.5907 0.2295 0.8312 0.055 Uiso 1 1 calc R . . C2 C 0.63940(14) 0.31528(12) 0.6884(2) 0.0518(5) Uani 1 1 d . . . H2A H 0.7032 0.2886 0.6549 0.062 Uiso 1 1 calc R . . C3 C 0.61066(14) 0.38998(12) 0.63315(19) 0.0508(4) Uani 1 1 d . . . H3A H 0.6551 0.4138 0.5614 0.061 Uiso 1 1 calc R . . C4 C 0.51605(13) 0.42986(10) 0.68367(18) 0.0442(4) Uani 1 1 d . . . H4A H 0.4973 0.4802 0.6449 0.053 Uiso 1 1 calc R . . C5 C 0.44875(12) 0.39572(9) 0.79164(16) 0.0370(4) Uani 1 1 d . . . C6 C 0.47770(12) 0.31934(9) 0.84791(16) 0.0382(4) Uani 1 1 d . . . C7 C 0.40105(13) 0.28056(10) 0.95836(17) 0.0417(4) Uani 1 1 d . . . H7A H 0.4347 0.2312 0.9966 0.050 Uiso 1 1 calc R . . H7B H 0.3888 0.3166 1.0415 0.050 Uiso 1 1 calc R . . C8 C 0.29108(12) 0.26303(9) 0.87738(16) 0.0358(3) Uani 1 1 d . . . C9 C 0.22348(12) 0.32281(9) 0.80129(15) 0.0337(3) Uani 1 1 d . . . C10 C 0.23915(12) 0.41229(9) 0.81627(16) 0.0345(3) Uani 1 1 d . . . H10A H 0.2175 0.4371 0.7206 0.041 Uiso 1 1 calc R . . C11 C 0.16087(14) 0.44553(10) 0.93496(19) 0.0436(4) Uani 1 1 d . . . H11A H 0.0833 0.4300 0.9104 0.052 Uiso 1 1 calc R . . H11B H 0.1817 0.4220 1.0308 0.052 Uiso 1 1 calc R . . C12 C 0.16774(15) 0.53643(10) 0.9465(2) 0.0503(4) Uani 1 1 d . . . H12A H 0.1351 0.5605 0.8567 0.060 Uiso 1 1 calc R . . H12B H 0.1243 0.5546 1.0304 0.060 Uiso 1 1 calc R . . C13 C 0.29004(16) 0.56316(11) 0.9673(2) 0.0545(5) Uani 1 1 d . . . H13A H 0.2940 0.6213 0.9592 0.065 Uiso 1 1 calc R . . H13B H 0.3176 0.5482 1.0663 0.065 Uiso 1 1 calc R . . C14 C 0.36507(14) 0.52550(9) 0.8524(2) 0.0469(4) Uani 1 1 d . . . H14A H 0.3425 0.5448 0.7539 0.056 Uiso 1 1 calc R . . H14B H 0.4432 0.5415 0.8721 0.056 Uiso 1 1 calc R . . C15 C 0.24665(13) 0.19101(9) 0.84058(17) 0.0383(4) Uani 1 1 d . . . C16 C 0.14003(12) 0.28221(9) 0.72417(16) 0.0342(3) Uani 1 1 d . . . C17 C 0.04475(12) 0.30238(9) 0.62344(16) 0.0349(3) Uani 1 1 d . . . C18 C -0.01154(13) 0.24098(10) 0.54511(18) 0.0416(4) Uani 1 1 d . . . H18A H 0.0110 0.1879 0.5602 0.050 Uiso 1 1 calc R . . C19 C -0.09983(14) 0.25747(11) 0.44580(19) 0.0467(4) Uani 1 1 d . . . H19A H -0.1358 0.2156 0.3946 0.056 Uiso 1 1 calc R . . C20 C -0.13499(14) 0.33526(11) 0.4218(2) 0.0502(4) Uani 1 1 d . . . H20A H -0.1938 0.3463 0.3536 0.060 Uiso 1 1 calc R . . C21 C -0.08231(15) 0.39653(11) 0.4998(2) 0.0562(5) Uani 1 1 d . . . H21A H -0.1063 0.4493 0.4850 0.067 Uiso 1 1 calc R . . C22 C 0.00612(14) 0.38058(10) 0.6001(2) 0.0484(4) Uani 1 1 d . . . H22A H 0.0402 0.4228 0.6528 0.058 Uiso 1 1 calc R . . C23 C 0.27839(17) 0.10673(10) 0.8757(2) 0.0549(5) Uani 1 1 d . . . H23A H 0.2249 0.0709 0.8280 0.082 Uiso 1 1 calc R . . H23B H 0.2780 0.0987 0.9816 0.082 Uiso 1 1 calc R . . H23C H 0.3529 0.0960 0.8402 0.082 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0403(6) 0.0309(5) 0.0447(6) 0.0016(4) -0.0020(5) 0.0009(4) N1 0.0326(7) 0.0361(7) 0.0443(7) -0.0028(5) -0.0019(5) -0.0021(5) C1 0.0382(9) 0.0513(10) 0.0482(9) -0.0042(7) -0.0079(7) 0.0065(7) C2 0.0363(9) 0.0686(12) 0.0505(10) -0.0127(8) 0.0019(7) 0.0044(8) C3 0.0397(9) 0.0693(12) 0.0438(9) -0.0038(8) 0.0049(7) -0.0090(8) C4 0.0391(8) 0.0502(10) 0.0429(8) 0.0018(7) -0.0030(7) -0.0071(7) C5 0.0301(7) 0.0444(9) 0.0363(7) -0.0033(6) -0.0052(6) -0.0034(6) C6 0.0318(7) 0.0461(9) 0.0362(8) -0.0018(6) -0.0071(6) 0.0001(6) C7 0.0409(8) 0.0455(9) 0.0382(8) 0.0050(7) -0.0054(6) 0.0037(7) C8 0.0345(7) 0.0388(8) 0.0341(7) 0.0055(6) 0.0026(6) 0.0028(6) C9 0.0318(7) 0.0348(8) 0.0347(7) 0.0018(6) 0.0026(6) 0.0006(6) C10 0.0321(7) 0.0342(8) 0.0369(7) 0.0020(6) -0.0021(6) -0.0007(6) C11 0.0403(8) 0.0424(9) 0.0485(9) -0.0002(7) 0.0066(7) 0.0019(7) C12 0.0510(10) 0.0431(9) 0.0573(10) -0.0073(8) 0.0076(8) 0.0063(7) C13 0.0564(11) 0.0411(9) 0.0655(11) -0.0138(8) -0.0047(9) -0.0002(8) C14 0.0411(9) 0.0381(9) 0.0611(10) -0.0036(7) -0.0033(7) -0.0059(7) C15 0.0376(8) 0.0384(8) 0.0390(8) 0.0055(6) 0.0009(6) 0.0047(6) C16 0.0345(7) 0.0298(7) 0.0384(7) 0.0019(6) 0.0032(6) 0.0015(6) C17 0.0291(7) 0.0362(8) 0.0394(8) 0.0018(6) 0.0033(6) -0.0005(6) C18 0.0392(8) 0.0384(8) 0.0472(9) -0.0030(7) -0.0001(7) 0.0017(6) C19 0.0389(8) 0.0533(10) 0.0477(9) -0.0049(7) -0.0039(7) -0.0038(7) C20 0.0342(8) 0.0626(11) 0.0534(10) 0.0107(8) -0.0067(7) -0.0013(7) C21 0.0453(9) 0.0424(10) 0.0801(13) 0.0137(9) -0.0109(9) 0.0033(7) C22 0.0413(9) 0.0365(8) 0.0669(11) 0.0028(8) -0.0099(8) -0.0030(7) C23 0.0637(11) 0.0399(10) 0.0607(11) 0.0085(8) -0.0060(9) 0.0078(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 O1 C15 1.3694(18) . ? O1 C16 1.3757(17) . ? N1 C5 1.4268(19) . ? N1 C14 1.463(2) . ? N1 C10 1.4820(18) . ? C1 C6 1.384(2) . ? C1 C2 1.386(2) . ? C1 H1A 0.9300 . ? C2 C3 1.376(3) . ? C2 H2A 0.9300 . ? C3 C4 1.385(2) . ? C3 H3A 0.9300 . ? C4 C5 1.390(2) . ? C4 H4A 0.9300 . ? C5 C6 1.405(2) . ? C6 C7 1.505(2) . ? C7 C8 1.497(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C15 1.344(2) . ? C8 C9 1.434(2) . ? C9 C16 1.365(2) . ? C9 C10 1.504(2) . ? C10 C11 1.532(2) . ? C10 H10A 0.9800 . ? C11 C12 1.516(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.515(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.513(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C23 1.481(2) . ? C16 C17 1.461(2) . ? C17 C22 1.391(2) . ? C17 C18 1.396(2) . ? C18 C19 1.379(2) . ? C18 H18A 0.9300 . ? C19 C20 1.373(3) . ? C19 H19A 0.9300 . ? C20 C21 1.374(3) . ? C20 H20A 0.9300 . ? C21 C22 1.384(2) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 C15 O1 C16 107.40(11) . . ? C5 N1 C14 115.17(12) . . ? C5 N1 C10 118.70(12) . . ? C14 N1 C10 110.01(12) . . ? C6 C1 C2 121.46(16) . . ? C6 C1 H1A 119.3 . . ? C2 C1 H1A 119.3 . . ? C3 C2 C1 119.12(15) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 120.42(16) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C3 C4 C5 120.90(16) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C4 C5 C6 118.78(14) . . ? C4 C5 N1 122.60(14) . . ? C6 C5 N1 118.43(13) . . ? C1 C6 C5 119.30(15) . . ? C1 C6 C7 121.97(15) . . ? C5 C6 C7 118.64(13) . . ? C8 C7 C6 106.97(12) . . ? C8 C7 H7A 110.3 . . ? C6 C7 H7A 110.3 . . ? C8 C7 H7B 110.3 . . ? C6 C7 H7B 110.3 . . ? H7A C7 H7B 108.6 . . ? C15 C8 C9 107.00(13) . . ? C15 C8 C7 128.23(14) . . ? C9 C8 C7 123.94(13) . . ? C16 C9 C8 106.37(13) . . ? C16 C9 C10 128.23(13) . . ? C8 C9 C10 125.24(13) . . ? N1 C10 C9 114.50(12) . . ? N1 C10 C11 107.89(12) . . ? C9 C10 C11 110.11(12) . . ? N1 C10 H10A 108.1 . . ? C9 C10 H10A 108.1 . . ? C11 C10 H10A 108.1 . . ? C12 C11 C10 112.02(13) . . ? C12 C11 H11A 109.2 . . ? C10 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C10 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C11 110.44(14) . . ? C13 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? C13 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? C14 C13 C12 111.57(14) . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? N1 C14 C13 110.84(14) . . ? N1 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C8 C15 O1 110.03(12) . . ? C8 C15 C23 134.06(15) . . ? O1 C15 C23 115.89(14) . . ? C9 C16 O1 109.19(12) . . ? C9 C16 C17 136.96(14) . . ? O1 C16 C17 113.82(12) . . ? C22 C17 C18 117.27(14) . . ? C22 C17 C16 123.38(14) . . ? C18 C17 C16 119.35(13) . . ? C19 C18 C17 121.30(15) . . ? C19 C18 H18A 119.3 . . ? C17 C18 H18A 119.3 . . ? C20 C19 C18 120.52(16) . . ? C20 C19 H19A 119.7 . . ? C18 C19 H19A 119.7 . . ? C19 C20 C21 119.20(16) . . ? C19 C20 H20A 120.4 . . ? C21 C20 H20A 120.4 . . ? C20 C21 C22 120.72(16) . . ? C20 C21 H21A 119.6 . . ? C22 C21 H21A 119.6 . . ? C21 C22 C17 120.95(16) . . ? C21 C22 H22A 119.5 . . ? C17 C22 H22A 119.5 . . ? C15 C23 H23A 109.5 . . ? C15 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C15 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.9(2) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 -0.6(2) . . . . ? C3 C4 C5 N1 174.33(14) . . . . ? C14 N1 C5 C4 -24.8(2) . . . . ? C10 N1 C5 C4 108.75(16) . . . . ? C14 N1 C5 C6 150.25(14) . . . . ? C10 N1 C5 C6 -76.25(17) . . . . ? C2 C1 C6 C5 0.7(2) . . . . ? C2 C1 C6 C7 177.30(14) . . . . ? C4 C5 C6 C1 0.1(2) . . . . ? N1 C5 C6 C1 -175.13(13) . . . . ? C4 C5 C6 C7 -176.61(13) . . . . ? N1 C5 C6 C7 8.2(2) . . . . ? C1 C6 C7 C8 -110.24(16) . . . . ? C5 C6 C7 C8 66.34(17) . . . . ? C6 C7 C8 C15 111.58(17) . . . . ? C6 C7 C8 C9 -56.59(19) . . . . ? C15 C8 C9 C16 1.01(16) . . . . ? C7 C8 C9 C16 171.32(13) . . . . ? C15 C8 C9 C10 176.78(13) . . . . ? C7 C8 C9 C10 -12.9(2) . . . . ? C5 N1 C10 C9 38.39(18) . . . . ? C14 N1 C10 C9 174.07(13) . . . . ? C5 N1 C10 C11 161.35(13) . . . . ? C14 N1 C10 C11 -62.97(15) . . . . ? C16 C9 C10 N1 -157.77(14) . . . . ? C8 C9 C10 N1 27.41(19) . . . . ? C16 C9 C10 C11 80.48(18) . . . . ? C8 C9 C10 C11 -94.35(16) . . . . ? N1 C10 C11 C12 58.34(17) . . . . ? C9 C10 C11 C12 -176.06(13) . . . . ? C10 C11 C12 C13 -52.42(19) . . . . ? C11 C12 C13 C14 50.3(2) . . . . ? C5 N1 C14 C13 -159.74(13) . . . . ? C10 N1 C14 C13 62.88(17) . . . . ? C12 C13 C14 N1 -56.0(2) . . . . ? C9 C8 C15 O1 -1.02(16) . . . . ? C7 C8 C15 O1 -170.78(13) . . . . ? C9 C8 C15 C23 177.17(17) . . . . ? C7 C8 C15 C23 7.4(3) . . . . ? C16 O1 C15 C8 0.64(16) . . . . ? C16 O1 C15 C23 -177.92(13) . . . . ? C8 C9 C16 O1 -0.63(15) . . . . ? C10 C9 C16 O1 -176.23(13) . . . . ? C8 C9 C16 C17 -178.79(16) . . . . ? C10 C9 C16 C17 5.6(3) . . . . ? C15 O1 C16 C9 0.03(15) . . . . ? C15 O1 C16 C17 178.65(12) . . . . ? C9 C16 C17 C22 -11.0(3) . . . . ? O1 C16 C17 C22 170.91(14) . . . . ? C9 C16 C17 C18 168.86(16) . . . . ? O1 C16 C17 C18 -9.23(19) . . . . ? C22 C17 C18 C19 1.7(2) . . . . ? C16 C17 C18 C19 -178.19(14) . . . . ? C17 C18 C19 C20 -0.2(3) . . . . ? C18 C19 C20 C21 -1.0(3) . . . . ? C19 C20 C21 C22 0.8(3) . . . . ? C20 C21 C22 C17 0.7(3) . . . . ? C18 C17 C22 C21 -1.9(2) . . . . ? C16 C17 C22 C21 177.95(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.353 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.034