# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Shi, Min' _publ_contact_author_email mshi@mail.sioc.ac.cn _publ_section_title ; Phosphine-catalyzed Highly Diastereoselective [3+2] Cyclization of Isatin Derived Electron-deficient Alkenes with -Allenic Esters ; loop_ _publ_author_name 'Min Shi' 'Xiu-Chun Zhang' 'Yin Wei' # Attachment '- cd201367.cif' data_cd201367 _database_code_depnum_ccdc_archive 'CCDC 783106' #TrackingRef '- cd201367.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H27 N O4' _chemical_formula_weight 465.53 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5001(12) _cell_length_b 10.6998(11) _cell_length_c 24.381(3) _cell_angle_alpha 81.545(2) _cell_angle_beta 83.868(2) _cell_angle_gamma 64.481(2) _cell_volume 2442.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1697 _cell_measurement_theta_min 4.700 _cell_measurement_theta_max 41.112 _exptl_crystal_description prisamatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.390 _exptl_crystal_size_mid 0.318 _exptl_crystal_size_min 0.157 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6515 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13419 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.1267 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 26.00 _reflns_number_total 9407 _reflns_number_gt 3623 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9407 _refine_ls_number_parameters 635 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1437 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_restrained_S_all 0.842 _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 O1 O 0.0281(2) 0.7543(2) 0.22700(10) 0.0670(7) Uani 1 1 d . . . O2 O 0.2312(3) 0.4326(2) 0.06594(10) 0.0757(8) Uani 1 1 d . . . O3 O 0.1589(3) 0.1561(2) 0.15127(13) 0.1007(10) Uani 1 1 d . . . O4 O 0.3204(2) 0.2251(2) 0.16796(10) 0.0655(7) Uani 1 1 d . . . O5 O 0.5940(2) 0.9168(2) 0.28206(9) 0.0650(7) Uani 1 1 d . . . O6 O 0.7619(3) 0.4773(2) 0.42551(10) 0.0784(8) Uani 1 1 d . . . O7 O 0.6978(2) 0.2639(2) 0.34753(10) 0.0789(8) Uani 1 1 d . . . O8 O 0.8650(3) 0.3407(2) 0.31838(10) 0.0679(7) Uani 1 1 d . . . N1 N -0.0424(3) 0.8757(2) 0.14165(11) 0.0466(7) Uani 1 1 d . . . N2 N 0.4924(3) 0.9654(2) 0.36934(11) 0.0485(7) Uani 1 1 d . . . C1 C -0.0068(3) 0.7622(3) 0.18018(15) 0.0488(8) Uani 1 1 d . . . C2 C -0.0165(3) 0.6422(3) 0.15387(12) 0.0439(8) Uani 1 1 d . . . C3 C -0.0658(3) 0.7115(3) 0.09691(13) 0.0449(8) Uani 1 1 d . . . C4 C -0.0776(3) 0.8492(3) 0.09167(13) 0.0466(8) Uani 1 1 d . . . C5 C -0.1195(3) 0.9393(3) 0.04410(14) 0.0578(9) Uani 1 1 d . . . H5 H -0.1276 1.0300 0.0413 0.069 Uiso 1 1 calc R . . C6 C -0.1493(4) 0.8876(4) 0.00020(14) 0.0693(11) Uani 1 1 d . . . H6 H -0.1782 0.9455 -0.0327 0.083 Uiso 1 1 calc R . . C7 C -0.1369(4) 0.7526(4) 0.00431(15) 0.0716(11) Uani 1 1 d . . . H7 H -0.1575 0.7215 -0.0258 0.086 Uiso 1 1 calc R . . C8 C -0.0944(3) 0.6630(3) 0.05258(14) 0.0595(10) Uani 1 1 d . . . H8 H -0.0853 0.5720 0.0550 0.071 Uiso 1 1 calc R . . C9 C -0.1151(3) 0.5826(3) 0.18890(13) 0.0531(9) Uani 1 1 d . . . H9 H -0.1074 0.5907 0.2278 0.064 Uiso 1 1 calc R . . C10 C -0.0424(4) 0.4311(3) 0.18207(12) 0.0529(9) Uani 1 1 d . . . H10 H -0.0857 0.3704 0.1902 0.063 Uiso 1 1 calc R . . C11 C 0.0897(4) 0.3925(3) 0.16325(13) 0.0472(8) Uani 1 1 d . . . C12 C 0.1307(3) 0.5119(3) 0.15283(12) 0.0452(8) Uani 1 1 d . . . H12 H 0.1844 0.5090 0.1838 0.054 Uiso 1 1 calc R . . C13 C 0.2181(3) 0.5116(3) 0.09901(14) 0.0509(9) Uani 1 1 d . . . C14 C 0.2889(3) 0.6085(3) 0.08762(15) 0.0534(9) Uani 1 1 d . . . C15 C 0.3455(4) 0.6252(4) 0.03404(17) 0.0824(12) Uani 1 1 d . . . H15 H 0.3344 0.5807 0.0061 0.099 Uiso 1 1 calc R . . C16 C 0.4193(5) 0.7096(5) 0.0224(2) 0.1127(17) Uani 1 1 d . . . H16 H 0.4584 0.7196 -0.0132 0.135 Uiso 1 1 calc R . . C17 C 0.4334(5) 0.7749(4) 0.0619(3) 0.1074(18) Uani 1 1 d . . . H17 H 0.4823 0.8306 0.0537 0.129 Uiso 1 1 calc R . . C18 C 0.3781(4) 0.7621(4) 0.1142(2) 0.0839(13) Uani 1 1 d . . . H18 H 0.3899 0.8087 0.1412 0.101 Uiso 1 1 calc R . . C19 C 0.3061(3) 0.6826(3) 0.12748(15) 0.0622(10) Uani 1 1 d . . . H19 H 0.2673 0.6765 0.1633 0.075 Uiso 1 1 calc R . . C20 C -0.2709(3) 0.6564(3) 0.17749(14) 0.0705(11) Uani 1 1 d . . . H20A H -0.2837 0.6503 0.1397 0.106 Uiso 1 1 calc R . . H20B H -0.3061 0.7525 0.1835 0.106 Uiso 1 1 calc R . . H20C H -0.3217 0.6130 0.2020 0.106 Uiso 1 1 calc R . . C21 C 0.1905(4) 0.2483(3) 0.15993(14) 0.0597(10) Uani 1 1 d . . . C22 C 0.4318(4) 0.0880(3) 0.16410(16) 0.0756(11) Uani 1 1 d . . . H22A H 0.3929 0.0195 0.1709 0.091 Uiso 1 1 calc R . . H22B H 0.4995 0.0670 0.1921 0.091 Uiso 1 1 calc R . . C23 C 0.5032(4) 0.0805(4) 0.10859(17) 0.1000(14) Uani 1 1 d . . . H23A H 0.4339 0.1203 0.0809 0.150 Uiso 1 1 calc R . . H23B H 0.5621 -0.0151 0.1034 0.150 Uiso 1 1 calc R . . H23C H 0.5604 0.1315 0.1052 0.150 Uiso 1 1 calc R . . C24 C -0.0238(3) 0.9976(3) 0.14915(14) 0.0586(9) Uani 1 1 d . . . H24A H 0.0266 1.0207 0.1165 0.070 Uiso 1 1 calc R . . H24B H 0.0348 0.9756 0.1805 0.070 Uiso 1 1 calc R . . C25 C -0.1586(3) 1.1231(3) 0.15882(14) 0.0477(8) Uani 1 1 d . . . C26 C -0.2020(4) 1.2413(4) 0.12090(14) 0.0668(10) Uani 1 1 d . . . H26 H -0.1474 1.2438 0.0884 0.080 Uiso 1 1 calc R . . C27 C -0.3265(5) 1.3560(4) 0.13115(18) 0.0796(12) Uani 1 1 d . . . H27 H -0.3558 1.4354 0.1056 0.096 Uiso 1 1 calc R . . C28 C -0.4062(4) 1.3521(4) 0.1790(2) 0.0844(13) Uani 1 1 d . . . H28 H -0.4894 1.4297 0.1859 0.101 Uiso 1 1 calc R . . C29 C -0.3650(4) 1.2351(4) 0.21693(16) 0.0788(12) Uani 1 1 d . . . H29 H -0.4197 1.2328 0.2494 0.095 Uiso 1 1 calc R . . C30 C -0.2423(4) 1.1223(3) 0.20618(15) 0.0630(10) Uani 1 1 d . . . H30 H -0.2146 1.0426 0.2316 0.076 Uiso 1 1 calc R . . C31 C 0.5434(3) 0.8852(3) 0.32639(15) 0.0533(9) Uani 1 1 d . . . C32 C 0.5284(3) 0.7452(3) 0.34318(13) 0.0475(8) Uani 1 1 d . . . C33 C 0.4595(3) 0.7651(3) 0.40095(13) 0.0467(8) Uani 1 1 d . . . C34 C 0.4402(3) 0.8978(3) 0.41355(13) 0.0484(8) Uani 1 1 d . . . C35 C 0.3753(3) 0.9487(3) 0.46244(14) 0.0593(9) Uani 1 1 d . . . H35 H 0.3613 1.0365 0.4701 0.071 Uiso 1 1 calc R . . C36 C 0.3314(4) 0.8617(5) 0.50016(14) 0.0755(12) Uani 1 1 d . . . H36 H 0.2877 0.8927 0.5339 0.091 Uiso 1 1 calc R . . C37 C 0.3510(4) 0.7266(4) 0.48899(15) 0.0704(11) Uani 1 1 d . . . H37 H 0.3206 0.6708 0.5148 0.084 Uiso 1 1 calc R . . C38 C 0.4162(4) 0.6818(3) 0.43895(14) 0.0621(10) Uani 1 1 d . . . H38 H 0.4309 0.5942 0.4309 0.075 Uiso 1 1 calc R . . C39 C 0.4426(3) 0.7176(3) 0.30237(13) 0.0546(9) Uani 1 1 d . . . H39 H 0.4687 0.7491 0.2649 0.065 Uiso 1 1 calc R . . C40 C 0.5089(4) 0.5621(3) 0.30841(13) 0.0564(9) Uani 1 1 d . . . H40 H 0.4653 0.5093 0.2990 0.068 Uiso 1 1 calc R . . C41 C 0.6345(4) 0.5078(3) 0.32819(13) 0.0509(9) Uani 1 1 d . . . C42 C 0.6756(3) 0.6171(3) 0.34126(12) 0.0462(8) Uani 1 1 d . . . H42 H 0.7350 0.6361 0.3104 0.055 Uiso 1 1 calc R . . C43 C 0.7527(3) 0.5782(3) 0.39465(14) 0.0511(9) Uani 1 1 d . . . C44 C 0.8201(3) 0.6708(3) 0.40836(15) 0.0532(9) Uani 1 1 d . . . C45 C 0.8615(4) 0.6564(4) 0.46279(16) 0.0796(12) Uani 1 1 d . . . H45 H 0.8427 0.5946 0.4897 0.096 Uiso 1 1 calc R . . C46 C 0.9289(5) 0.7308(5) 0.4772(2) 0.1043(17) Uani 1 1 d . . . H46 H 0.9564 0.7191 0.5133 0.125 Uiso 1 1 calc R . . C47 C 0.9545(5) 0.8207(5) 0.4384(3) 0.1060(18) Uani 1 1 d . . . H47 H 1.0000 0.8716 0.4480 0.127 Uiso 1 1 calc R . . C48 C 0.9157(4) 0.8393(4) 0.3857(2) 0.0848(13) Uani 1 1 d . . . H48 H 0.9351 0.9024 0.3596 0.102 Uiso 1 1 calc R . . C49 C 0.8490(3) 0.7673(3) 0.37017(15) 0.0611(10) Uani 1 1 d . . . H49 H 0.8221 0.7822 0.3338 0.073 Uiso 1 1 calc R . . C50 C 0.2834(3) 0.7891(4) 0.30952(15) 0.0762(12) Uani 1 1 d . . . H50A H 0.2421 0.7670 0.2812 0.114 Uiso 1 1 calc R . . H50B H 0.2533 0.8881 0.3065 0.114 Uiso 1 1 calc R . . H50C H 0.2537 0.7574 0.3454 0.114 Uiso 1 1 calc R . . C51 C 0.7331(4) 0.3599(4) 0.33342(14) 0.0590(10) Uani 1 1 d . . . C52 C 0.9734(4) 0.1995(4) 0.32407(17) 0.0804(12) Uani 1 1 d . . . H52A H 1.0507 0.1915 0.2971 0.096 Uiso 1 1 calc R . . H52B H 0.9350 0.1362 0.3167 0.096 Uiso 1 1 calc R . . C53 C 1.0269(4) 0.1604(4) 0.38050(17) 0.0974(14) Uani 1 1 d . . . H53A H 1.0818 0.2100 0.3851 0.146 Uiso 1 1 calc R . . H53B H 1.0851 0.0619 0.3858 0.146 Uiso 1 1 calc R . . H53C H 0.9487 0.1837 0.4073 0.146 Uiso 1 1 calc R . . C54 C 0.5169(3) 1.0859(3) 0.37249(14) 0.0582(9) Uani 1 1 d . . . H54A H 0.5927 1.0850 0.3458 0.070 Uiso 1 1 calc R . . H54B H 0.5478 1.0805 0.4092 0.070 Uiso 1 1 calc R . . C55 C 0.3896(3) 1.2208(3) 0.36140(14) 0.0471(8) Uani 1 1 d . . . C56 C 0.3495(4) 1.3213(4) 0.39637(15) 0.0692(11) Uani 1 1 d . . . H56 H 0.3970 1.3025 0.4288 0.083 Uiso 1 1 calc R . . C57 C 0.2380(4) 1.4522(4) 0.38405(18) 0.0853(13) Uani 1 1 d . . . H57 H 0.2119 1.5213 0.4075 0.102 Uiso 1 1 calc R . . C58 C 0.1682(4) 1.4760(4) 0.3363(2) 0.0820(13) Uani 1 1 d . . . H58 H 0.0944 1.5625 0.3272 0.098 Uiso 1 1 calc R . . C59 C 0.2054(4) 1.3756(4) 0.30280(16) 0.0762(12) Uani 1 1 d . . . H59 H 0.1555 1.3919 0.2712 0.091 Uiso 1 1 calc R . . C60 C 0.3155(4) 1.2505(3) 0.31490(14) 0.0612(10) Uani 1 1 d . . . H60 H 0.3414 1.1830 0.2908 0.073 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 0.0877(18) 0.0619(16) 0.0542(16) -0.0093(12) -0.0226(14) -0.0289(14) O2 0.0974(19) 0.0747(18) 0.0737(18) -0.0365(14) 0.0200(14) -0.0506(16) O3 0.0724(19) 0.0527(18) 0.184(3) -0.0180(17) -0.0194(18) -0.0287(16) O4 0.0530(15) 0.0425(15) 0.103(2) -0.0157(12) -0.0121(14) -0.0182(13) O5 0.0748(17) 0.0618(16) 0.0523(16) 0.0102(12) 0.0053(13) -0.0301(14) O6 0.103(2) 0.0643(18) 0.0768(18) 0.0300(13) -0.0279(15) -0.0505(16) O7 0.0706(17) 0.0599(17) 0.110(2) -0.0118(14) 0.0026(15) -0.0320(15) O8 0.0561(16) 0.0420(15) 0.103(2) -0.0046(12) 0.0065(14) -0.0216(13) N1 0.0536(17) 0.0332(16) 0.0568(18) -0.0071(13) -0.0081(14) -0.0202(14) N2 0.0576(18) 0.0334(16) 0.0524(18) -0.0053(13) 0.0006(14) -0.0179(14) C1 0.045(2) 0.043(2) 0.055(2) -0.0118(18) -0.0033(17) -0.0135(17) C2 0.052(2) 0.0366(19) 0.048(2) -0.0089(15) -0.0049(16) -0.0215(17) C3 0.045(2) 0.039(2) 0.051(2) -0.0060(16) -0.0069(16) -0.0166(16) C4 0.0392(19) 0.048(2) 0.050(2) -0.0071(17) 0.0006(16) -0.0159(17) C5 0.070(2) 0.046(2) 0.055(2) -0.0002(18) -0.0079(19) -0.0226(19) C6 0.076(3) 0.066(3) 0.054(2) 0.005(2) -0.010(2) -0.021(2) C7 0.084(3) 0.079(3) 0.053(3) -0.011(2) -0.013(2) -0.033(2) C8 0.072(2) 0.055(2) 0.056(2) -0.0082(19) -0.0140(19) -0.027(2) C9 0.054(2) 0.054(2) 0.052(2) -0.0066(16) 0.0033(17) -0.0245(19) C10 0.059(2) 0.045(2) 0.062(2) -0.0015(16) -0.0095(19) -0.0283(19) C11 0.052(2) 0.030(2) 0.061(2) -0.0071(15) -0.0068(18) -0.0181(17) C12 0.050(2) 0.0351(19) 0.053(2) -0.0081(15) -0.0076(17) -0.0181(17) C13 0.048(2) 0.044(2) 0.061(2) -0.0052(17) -0.0027(18) -0.0196(18) C14 0.042(2) 0.042(2) 0.067(3) 0.0036(17) -0.0029(18) -0.0120(17) C15 0.096(3) 0.068(3) 0.076(3) 0.003(2) 0.000(2) -0.033(2) C16 0.136(4) 0.100(4) 0.115(4) 0.019(3) 0.024(3) -0.078(4) C17 0.110(4) 0.067(3) 0.164(6) 0.011(3) -0.006(4) -0.062(3) C18 0.075(3) 0.055(3) 0.137(4) -0.007(3) -0.010(3) -0.042(2) C19 0.053(2) 0.053(2) 0.083(3) -0.009(2) -0.008(2) -0.024(2) C20 0.055(2) 0.060(2) 0.087(3) -0.0093(19) 0.009(2) -0.019(2) C21 0.066(3) 0.044(2) 0.081(3) -0.0066(18) -0.008(2) -0.034(2) C22 0.062(3) 0.047(2) 0.105(3) -0.002(2) -0.010(2) -0.013(2) C23 0.089(3) 0.081(3) 0.104(4) -0.014(3) 0.016(3) -0.015(3) C24 0.059(2) 0.045(2) 0.081(3) -0.0134(18) -0.0046(19) -0.0276(19) C25 0.053(2) 0.032(2) 0.061(2) -0.0102(17) -0.0079(19) -0.0182(18) C26 0.085(3) 0.049(2) 0.067(3) -0.009(2) -0.006(2) -0.027(2) C27 0.100(3) 0.044(3) 0.083(3) 0.001(2) -0.032(3) -0.015(3) C28 0.070(3) 0.065(3) 0.099(4) -0.038(3) -0.015(3) 0.001(2) C29 0.079(3) 0.064(3) 0.080(3) -0.014(2) 0.003(2) -0.017(3) C30 0.068(3) 0.044(2) 0.068(3) -0.0044(18) -0.005(2) -0.015(2) C31 0.044(2) 0.050(2) 0.055(2) 0.0093(19) -0.0107(18) -0.0127(18) C32 0.055(2) 0.037(2) 0.051(2) -0.0020(15) 0.0001(17) -0.0206(17) C33 0.050(2) 0.042(2) 0.049(2) -0.0019(16) -0.0051(17) -0.0207(17) C34 0.043(2) 0.048(2) 0.049(2) 0.0021(17) -0.0057(17) -0.0158(17) C35 0.068(2) 0.054(2) 0.055(2) -0.0118(19) 0.000(2) -0.023(2) C36 0.061(3) 0.110(4) 0.044(2) -0.007(2) 0.0010(19) -0.026(3) C37 0.079(3) 0.075(3) 0.062(3) 0.002(2) 0.001(2) -0.042(2) C38 0.075(3) 0.057(2) 0.061(3) -0.0060(19) 0.009(2) -0.037(2) C39 0.055(2) 0.050(2) 0.059(2) -0.0095(17) -0.0073(18) -0.0204(19) C40 0.059(2) 0.050(2) 0.070(3) -0.0155(18) -0.0013(19) -0.029(2) C41 0.054(2) 0.036(2) 0.066(2) -0.0071(16) -0.0005(18) -0.0218(18) C42 0.051(2) 0.0374(19) 0.051(2) -0.0027(15) -0.0006(16) -0.0210(17) C43 0.050(2) 0.046(2) 0.056(2) -0.0040(17) -0.0001(18) -0.0193(18) C44 0.043(2) 0.043(2) 0.062(2) -0.0080(17) -0.0022(18) -0.0071(17) C45 0.082(3) 0.081(3) 0.059(3) -0.006(2) -0.006(2) -0.019(2) C46 0.118(4) 0.102(4) 0.117(4) -0.042(3) -0.037(3) -0.053(3) C47 0.094(4) 0.068(3) 0.173(6) -0.029(3) -0.023(4) -0.042(3) C48 0.077(3) 0.053(3) 0.136(4) -0.002(3) -0.023(3) -0.037(2) C49 0.054(2) 0.044(2) 0.083(3) -0.0008(19) -0.009(2) -0.0185(19) C50 0.060(3) 0.075(3) 0.091(3) -0.020(2) -0.014(2) -0.020(2) C51 0.071(3) 0.050(3) 0.071(3) -0.0060(18) 0.000(2) -0.041(2) C52 0.066(3) 0.055(3) 0.109(4) -0.006(2) -0.003(2) -0.017(2) C53 0.092(3) 0.073(3) 0.103(4) 0.005(2) -0.011(3) -0.016(3) C54 0.063(2) 0.034(2) 0.079(3) 0.0004(16) -0.0154(19) -0.0205(18) C55 0.048(2) 0.034(2) 0.060(2) -0.0062(17) 0.0012(18) -0.0188(17) C56 0.078(3) 0.059(3) 0.066(3) -0.002(2) -0.010(2) -0.025(2) C57 0.087(3) 0.053(3) 0.095(3) -0.024(2) 0.024(3) -0.012(3) C58 0.051(3) 0.067(3) 0.098(4) 0.025(3) -0.004(2) -0.008(2) C59 0.083(3) 0.065(3) 0.070(3) -0.001(2) -0.013(2) -0.021(3) C60 0.061(2) 0.043(2) 0.067(3) 0.0026(18) -0.011(2) -0.011(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.216(3) . ? O2 C13 1.208(3) . ? O3 C21 1.219(3) . ? O4 C21 1.308(4) . ? O4 C22 1.438(3) . ? O5 C31 1.220(4) . ? O6 C43 1.196(4) . ? O7 C51 1.227(4) . ? O8 C51 1.328(4) . ? O8 C52 1.445(3) . ? N1 C1 1.358(4) . ? N1 C4 1.411(3) . ? N1 C24 1.439(3) . ? N2 C31 1.367(4) . ? N2 C34 1.404(4) . ? N2 C54 1.433(3) . ? C1 C2 1.562(4) . ? C2 C3 1.505(4) . ? C2 C9 1.558(4) . ? C2 C12 1.575(4) . ? C3 C8 1.376(4) . ? C3 C4 1.412(4) . ? C4 C5 1.372(4) . ? C5 C6 1.394(4) . ? C5 H5 0.9300 . ? C6 C7 1.383(4) . ? C6 H6 0.9300 . ? C7 C8 1.384(4) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.492(4) . ? C9 C20 1.515(4) . ? C9 H9 0.9800 . ? C10 C11 1.316(4) . ? C10 H10 0.9300 . ? C11 C21 1.456(4) . ? C11 C12 1.495(4) . ? C12 C13 1.518(4) . ? C12 H12 0.9800 . ? C13 C14 1.497(4) . ? C14 C15 1.396(5) . ? C14 C19 1.411(4) . ? C15 C16 1.406(5) . ? C15 H15 0.9300 . ? C16 C17 1.327(5) . ? C16 H16 0.9300 . ? C17 C18 1.356(6) . ? C17 H17 0.9300 . ? C18 C19 1.350(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C22 C23 1.471(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.499(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C30 1.376(4) . ? C25 C26 1.383(4) . ? C26 C27 1.384(4) . ? C26 H26 0.9300 . ? C27 C28 1.368(5) . ? C27 H27 0.9300 . ? C28 C29 1.374(5) . ? C28 H28 0.9300 . ? C29 C30 1.366(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C32 1.564(4) . ? C32 C33 1.513(4) . ? C32 C39 1.548(4) . ? C32 C42 1.564(4) . ? C33 C38 1.370(4) . ? C33 C34 1.420(4) . ? C34 C35 1.371(4) . ? C35 C36 1.397(5) . ? C35 H35 0.9300 . ? C36 C37 1.433(5) . ? C36 H36 0.9300 . ? C37 C38 1.377(4) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C39 C40 1.492(4) . ? C39 C50 1.512(4) . ? C39 H39 0.9800 . ? C40 C41 1.305(4) . ? C40 H40 0.9300 . ? C41 C51 1.467(4) . ? C41 C42 1.493(4) . ? C42 C43 1.516(4) . ? C42 H42 0.9800 . ? C43 C44 1.531(4) . ? C44 C49 1.397(4) . ? C44 C45 1.407(4) . ? C45 C46 1.371(5) . ? C45 H45 0.9300 . ? C46 C47 1.338(6) . ? C46 H46 0.9300 . ? C47 C48 1.352(6) . ? C47 H47 0.9300 . ? C48 C49 1.354(4) . ? C48 H48 0.9300 . ? C49 H49 0.9300 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? C52 C53 1.475(4) . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C53 H53A 0.9600 . ? C53 H53B 0.9600 . ? C53 H53C 0.9600 . ? C54 C55 1.498(4) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C55 C60 1.364(4) . ? C55 C56 1.365(4) . ? C56 C57 1.401(4) . ? C56 H56 0.9300 . ? C57 C58 1.375(5) . ? C57 H57 0.9300 . ? C58 C59 1.343(5) . ? C58 H58 0.9300 . ? C59 C60 1.356(4) . ? C59 H59 0.9300 . ? C60 H60 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 C21 O4 C22 119.5(3) . . ? C51 O8 C52 117.5(3) . . ? C1 N1 C4 111.4(3) . . ? C1 N1 C24 122.7(3) . . ? C4 N1 C24 125.2(3) . . ? C31 N2 C34 110.4(3) . . ? C31 N2 C54 123.4(3) . . ? C34 N2 C54 125.0(3) . . ? O1 C1 N1 126.1(3) . . ? O1 C1 C2 125.6(3) . . ? N1 C1 C2 108.3(3) . . ? C3 C2 C9 114.7(2) . . ? C3 C2 C1 102.0(2) . . ? C9 C2 C1 112.7(2) . . ? C3 C2 C12 113.4(2) . . ? C9 C2 C12 103.3(2) . . ? C1 C2 C12 111.1(2) . . ? C8 C3 C4 119.5(3) . . ? C8 C3 C2 131.9(3) . . ? C4 C3 C2 108.5(3) . . ? C5 C4 N1 127.6(3) . . ? C5 C4 C3 122.6(3) . . ? N1 C4 C3 109.8(3) . . ? C4 C5 C6 116.5(3) . . ? C4 C5 H5 121.8 . . ? C6 C5 H5 121.8 . . ? C7 C6 C5 121.8(3) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C8 121.0(3) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C3 C8 C7 118.6(3) . . ? C3 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C10 C9 C20 117.0(3) . . ? C10 C9 C2 102.8(2) . . ? C20 C9 C2 116.6(3) . . ? C10 C9 H9 106.6 . . ? C20 C9 H9 106.6 . . ? C2 C9 H9 106.6 . . ? C11 C10 C9 112.7(3) . . ? C11 C10 H10 123.7 . . ? C9 C10 H10 123.7 . . ? C10 C11 C21 124.2(3) . . ? C10 C11 C12 112.2(3) . . ? C21 C11 C12 123.1(3) . . ? C11 C12 C13 113.3(2) . . ? C11 C12 C2 102.6(2) . . ? C13 C12 C2 113.5(2) . . ? C11 C12 H12 109.1 . . ? C13 C12 H12 109.1 . . ? C2 C12 H12 109.1 . . ? O2 C13 C14 120.4(3) . . ? O2 C13 C12 120.0(3) . . ? C14 C13 C12 119.6(3) . . ? C15 C14 C19 117.0(3) . . ? C15 C14 C13 118.1(3) . . ? C19 C14 C13 124.9(3) . . ? C14 C15 C16 119.9(4) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 120.1(5) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 121.4(5) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C19 C18 C17 120.8(4) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C14 120.8(4) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? C9 C20 H20A 109.5 . . ? C9 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C9 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21 O4 122.3(3) . . ? O3 C21 C11 124.2(3) . . ? O4 C21 C11 113.5(3) . . ? O4 C22 C23 110.0(3) . . ? O4 C22 H22A 109.7 . . ? C23 C22 H22A 109.7 . . ? O4 C22 H22B 109.7 . . ? C23 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N1 C24 C25 114.5(3) . . ? N1 C24 H24A 108.6 . . ? C25 C24 H24A 108.6 . . ? N1 C24 H24B 108.6 . . ? C25 C24 H24B 108.6 . . ? H24A C24 H24B 107.6 . . ? C30 C25 C26 118.5(3) . . ? C30 C25 C24 120.1(3) . . ? C26 C25 C24 121.4(3) . . ? C25 C26 C27 120.1(4) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C28 C27 C26 119.8(4) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C27 C28 C29 120.8(4) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C30 C29 C28 118.8(4) . . ? C30 C29 H29 120.6 . . ? C28 C29 H29 120.6 . . ? C29 C30 C25 121.9(3) . . ? C29 C30 H30 119.0 . . ? C25 C30 H30 119.0 . . ? O5 C31 N2 125.6(3) . . ? O5 C31 C32 125.1(3) . . ? N2 C31 C32 109.3(3) . . ? C33 C32 C39 114.0(3) . . ? C33 C32 C31 101.5(2) . . ? C39 C32 C31 113.3(3) . . ? C33 C32 C42 113.8(2) . . ? C39 C32 C42 103.5(2) . . ? C31 C32 C42 111.2(3) . . ? C38 C33 C34 119.9(3) . . ? C38 C33 C32 131.9(3) . . ? C34 C33 C32 108.2(3) . . ? C35 C34 N2 127.0(3) . . ? C35 C34 C33 122.3(3) . . ? N2 C34 C33 110.7(3) . . ? C34 C35 C36 116.4(3) . . ? C34 C35 H35 121.8 . . ? C36 C35 H35 121.8 . . ? C35 C36 C37 122.7(3) . . ? C35 C36 H36 118.7 . . ? C37 C36 H36 118.7 . . ? C38 C37 C36 118.1(3) . . ? C38 C37 H37 121.0 . . ? C36 C37 H37 121.0 . . ? C33 C38 C37 120.7(3) . . ? C33 C38 H38 119.7 . . ? C37 C38 H38 119.7 . . ? C40 C39 C50 116.9(3) . . ? C40 C39 C32 100.6(2) . . ? C50 C39 C32 117.1(3) . . ? C40 C39 H39 107.2 . . ? C50 C39 H39 107.2 . . ? C32 C39 H39 107.2 . . ? C41 C40 C39 113.0(3) . . ? C41 C40 H40 123.5 . . ? C39 C40 H40 123.5 . . ? C40 C41 C51 126.4(3) . . ? C40 C41 C42 111.8(3) . . ? C51 C41 C42 121.6(3) . . ? C41 C42 C43 113.4(3) . . ? C41 C42 C32 101.1(2) . . ? C43 C42 C32 113.8(2) . . ? C41 C42 H42 109.4 . . ? C43 C42 H42 109.4 . . ? C32 C42 H42 109.4 . . ? O6 C43 C42 121.1(3) . . ? O6 C43 C44 120.3(3) . . ? C42 C43 C44 118.6(3) . . ? C49 C44 C45 116.2(3) . . ? C49 C44 C43 125.0(3) . . ? C45 C44 C43 118.8(3) . . ? C46 C45 C44 121.8(4) . . ? C46 C45 H45 119.1 . . ? C44 C45 H45 119.1 . . ? C47 C46 C45 118.9(5) . . ? C47 C46 H46 120.6 . . ? C45 C46 H46 120.6 . . ? C46 C47 C48 121.6(5) . . ? C46 C47 H47 119.2 . . ? C48 C47 H47 119.2 . . ? C47 C48 C49 120.9(4) . . ? C47 C48 H48 119.6 . . ? C49 C48 H48 119.6 . . ? C48 C49 C44 120.6(4) . . ? C48 C49 H49 119.7 . . ? C44 C49 H49 119.7 . . ? C39 C50 H50A 109.5 . . ? C39 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C39 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? O7 C51 O8 123.4(3) . . ? O7 C51 C41 124.3(3) . . ? O8 C51 C41 112.2(3) . . ? O8 C52 C53 110.7(3) . . ? O8 C52 H52A 109.5 . . ? C53 C52 H52A 109.5 . . ? O8 C52 H52B 109.5 . . ? C53 C52 H52B 109.5 . . ? H52A C52 H52B 108.1 . . ? C52 C53 H53A 109.5 . . ? C52 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C52 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? N2 C54 C55 113.7(3) . . ? N2 C54 H54A 108.8 . . ? C55 C54 H54A 108.8 . . ? N2 C54 H54B 108.8 . . ? C55 C54 H54B 108.8 . . ? H54A C54 H54B 107.7 . . ? C60 C55 C56 118.0(3) . . ? C60 C55 C54 121.6(3) . . ? C56 C55 C54 120.3(3) . . ? C55 C56 C57 120.9(4) . . ? C55 C56 H56 119.6 . . ? C57 C56 H56 119.6 . . ? C58 C57 C56 118.2(4) . . ? C58 C57 H57 120.9 . . ? C56 C57 H57 120.9 . . ? C59 C58 C57 120.7(4) . . ? C59 C58 H58 119.7 . . ? C57 C58 H58 119.7 . . ? C58 C59 C60 120.1(4) . . ? C58 C59 H59 119.9 . . ? C60 C59 H59 119.9 . . ? C59 C60 C55 122.0(3) . . ? C59 C60 H60 119.0 . . ? C55 C60 H60 119.0 . . ? 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 C4 N1 C1 O1 -179.9(3) . . . . ? C24 N1 C1 O1 9.2(5) . . . . ? C4 N1 C1 C2 0.7(3) . . . . ? C24 N1 C1 C2 -170.2(3) . . . . ? O1 C1 C2 C3 179.2(3) . . . . ? N1 C1 C2 C3 -1.4(3) . . . . ? O1 C1 C2 C9 55.7(4) . . . . ? N1 C1 C2 C9 -124.9(3) . . . . ? O1 C1 C2 C12 -59.7(4) . . . . ? N1 C1 C2 C12 119.7(3) . . . . ? C9 C2 C3 C8 -58.4(4) . . . . ? C1 C2 C3 C8 179.5(3) . . . . ? C12 C2 C3 C8 59.9(4) . . . . ? C9 C2 C3 C4 123.7(3) . . . . ? C1 C2 C3 C4 1.6(3) . . . . ? C12 C2 C3 C4 -118.0(3) . . . . ? C1 N1 C4 C5 179.5(3) . . . . ? C24 N1 C4 C5 -9.9(5) . . . . ? C1 N1 C4 C3 0.3(4) . . . . ? C24 N1 C4 C3 171.0(3) . . . . ? C8 C3 C4 C5 1.3(5) . . . . ? C2 C3 C4 C5 179.5(3) . . . . ? C8 C3 C4 N1 -179.5(3) . . . . ? C2 C3 C4 N1 -1.3(3) . . . . ? N1 C4 C5 C6 -179.6(3) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C4 C5 C6 C7 -0.1(5) . . . . ? C5 C6 C7 C8 0.1(6) . . . . ? C4 C3 C8 C7 -1.3(5) . . . . ? C2 C3 C8 C7 -179.0(3) . . . . ? C6 C7 C8 C3 0.7(5) . . . . ? C3 C2 C9 C10 99.9(3) . . . . ? C1 C2 C9 C10 -143.9(3) . . . . ? C12 C2 C9 C10 -23.9(3) . . . . ? C3 C2 C9 C20 -29.4(4) . . . . ? C1 C2 C9 C20 86.7(3) . . . . ? C12 C2 C9 C20 -153.3(3) . . . . ? C20 C9 C10 C11 145.6(3) . . . . ? C2 C9 C10 C11 16.5(3) . . . . ? C9 C10 C11 C21 171.2(3) . . . . ? C9 C10 C11 C12 -1.0(4) . . . . ? C10 C11 C12 C13 -137.5(3) . . . . ? C21 C11 C12 C13 50.2(4) . . . . ? C10 C11 C12 C2 -14.8(3) . . . . ? C21 C11 C12 C2 172.9(3) . . . . ? C3 C2 C12 C11 -101.3(3) . . . . ? C9 C2 C12 C11 23.4(3) . . . . ? C1 C2 C12 C11 144.5(3) . . . . ? C3 C2 C12 C13 21.3(3) . . . . ? C9 C2 C12 C13 146.0(3) . . . . ? C1 C2 C12 C13 -92.9(3) . . . . ? C11 C12 C13 O2 10.2(4) . . . . ? C2 C12 C13 O2 -106.3(3) . . . . ? C11 C12 C13 C14 -169.1(3) . . . . ? C2 C12 C13 C14 74.5(3) . . . . ? O2 C13 C14 C15 12.7(5) . . . . ? C12 C13 C14 C15 -168.0(3) . . . . ? O2 C13 C14 C19 -165.8(3) . . . . ? C12 C13 C14 C19 13.5(4) . . . . ? C19 C14 C15 C16 1.9(5) . . . . ? C13 C14 C15 C16 -176.7(3) . . . . ? C14 C15 C16 C17 -1.0(7) . . . . ? C15 C16 C17 C18 0.2(8) . . . . ? C16 C17 C18 C19 -0.3(7) . . . . ? C17 C18 C19 C14 1.3(6) . . . . ? C15 C14 C19 C18 -2.0(5) . . . . ? C13 C14 C19 C18 176.4(3) . . . . ? C22 O4 C21 O3 2.9(5) . . . . ? C22 O4 C21 C11 -178.0(3) . . . . ? C10 C11 C21 O3 32.1(5) . . . . ? C12 C11 C21 O3 -156.5(3) . . . . ? C10 C11 C21 O4 -147.0(3) . . . . ? C12 C11 C21 O4 24.4(4) . . . . ? C21 O4 C22 C23 97.0(4) . . . . ? C1 N1 C24 C25 -109.3(3) . . . . ? C4 N1 C24 C25 81.1(4) . . . . ? N1 C24 C25 C30 65.4(4) . . . . ? N1 C24 C25 C26 -114.5(3) . . . . ? C30 C25 C26 C27 0.6(5) . . . . ? C24 C25 C26 C27 -179.5(3) . . . . ? C25 C26 C27 C28 0.2(6) . . . . ? C26 C27 C28 C29 -0.6(6) . . . . ? C27 C28 C29 C30 0.2(6) . . . . ? C28 C29 C30 C25 0.6(6) . . . . ? C26 C25 C30 C29 -1.0(5) . . . . ? C24 C25 C30 C29 179.1(3) . . . . ? C34 N2 C31 O5 179.1(3) . . . . ? C54 N2 C31 O5 -13.0(5) . . . . ? C34 N2 C31 C32 -1.5(3) . . . . ? C54 N2 C31 C32 166.4(3) . . . . ? O5 C31 C32 C33 -179.7(3) . . . . ? N2 C31 C32 C33 1.0(3) . . . . ? O5 C31 C32 C39 -57.0(4) . . . . ? N2 C31 C32 C39 123.6(3) . . . . ? O5 C31 C32 C42 59.0(4) . . . . ? N2 C31 C32 C42 -120.4(3) . . . . ? C39 C32 C33 C38 57.2(5) . . . . ? C31 C32 C33 C38 179.3(3) . . . . ? C42 C32 C33 C38 -61.2(5) . . . . ? C39 C32 C33 C34 -122.2(3) . . . . ? C31 C32 C33 C34 0.0(3) . . . . ? C42 C32 C33 C34 119.4(3) . . . . ? C31 N2 C34 C35 -176.9(3) . . . . ? C54 N2 C34 C35 15.4(5) . . . . ? C31 N2 C34 C33 1.6(4) . . . . ? C54 N2 C34 C33 -166.2(3) . . . . ? C38 C33 C34 C35 -1.8(5) . . . . ? C32 C33 C34 C35 177.6(3) . . . . ? C38 C33 C34 N2 179.7(3) . . . . ? C32 C33 C34 N2 -0.9(3) . . . . ? N2 C34 C35 C36 179.6(3) . . . . ? C33 C34 C35 C36 1.3(5) . . . . ? C34 C35 C36 C37 -0.5(5) . . . . ? C35 C36 C37 C38 0.2(5) . . . . ? C34 C33 C38 C37 1.4(5) . . . . ? C32 C33 C38 C37 -177.9(3) . . . . ? C36 C37 C38 C33 -0.6(5) . . . . ? C33 C32 C39 C40 -94.2(3) . . . . ? C31 C32 C39 C40 150.5(3) . . . . ? C42 C32 C39 C40 30.0(3) . . . . ? C33 C32 C39 C50 33.6(4) . . . . ? C31 C32 C39 C50 -81.8(4) . . . . ? C42 C32 C39 C50 157.8(3) . . . . ? C50 C39 C40 C41 -148.8(3) . . . . ? C32 C39 C40 C41 -20.9(4) . . . . ? C39 C40 C41 C51 -173.0(3) . . . . ? C39 C40 C41 C42 1.9(4) . . . . ? C40 C41 C42 C43 140.0(3) . . . . ? C51 C41 C42 C43 -44.8(4) . . . . ? C40 C41 C42 C32 17.8(4) . . . . ? C51 C41 C42 C32 -167.0(3) . . . . ? C33 C32 C42 C41 95.0(3) . . . . ? C39 C32 C42 C41 -29.3(3) . . . . ? C31 C32 C42 C41 -151.1(3) . . . . ? C33 C32 C42 C43 -26.9(4) . . . . ? C39 C32 C42 C43 -151.2(3) . . . . ? C31 C32 C42 C43 86.9(3) . . . . ? C41 C42 C43 O6 -8.7(5) . . . . ? C32 C42 C43 O6 106.2(4) . . . . ? C41 C42 C43 C44 170.9(3) . . . . ? C32 C42 C43 C44 -74.2(3) . . . . ? O6 C43 C44 C49 162.2(3) . . . . ? C42 C43 C44 C49 -17.4(5) . . . . ? O6 C43 C44 C45 -15.4(5) . . . . ? C42 C43 C44 C45 164.9(3) . . . . ? C49 C44 C45 C46 -1.2(5) . . . . ? C43 C44 C45 C46 176.6(3) . . . . ? C44 C45 C46 C47 0.7(7) . . . . ? C45 C46 C47 C48 -0.1(8) . . . . ? C46 C47 C48 C49 0.1(7) . . . . ? C47 C48 C49 C44 -0.7(6) . . . . ? C45 C44 C49 C48 1.2(5) . . . . ? C43 C44 C49 C48 -176.5(3) . . . . ? C52 O8 C51 O7 -6.0(5) . . . . ? C52 O8 C51 C41 177.2(3) . . . . ? C40 C41 C51 O7 -39.2(6) . . . . ? C42 C41 C51 O7 146.3(3) . . . . ? C40 C41 C51 O8 137.6(4) . . . . ? C42 C41 C51 O8 -36.9(4) . . . . ? C51 O8 C52 C53 -86.5(4) . . . . ? C31 N2 C54 C55 106.6(3) . . . . ? C34 N2 C54 C55 -87.3(4) . . . . ? N2 C54 C55 C60 -52.3(4) . . . . ? N2 C54 C55 C56 131.6(3) . . . . ? C60 C55 C56 C57 -1.6(5) . . . . ? C54 C55 C56 C57 174.6(3) . . . . ? C55 C56 C57 C58 1.2(6) . . . . ? C56 C57 C58 C59 0.6(6) . . . . ? C57 C58 C59 C60 -2.0(6) . . . . ? C58 C59 C60 C55 1.6(6) . . . . ? C56 C55 C60 C59 0.2(5) . . . . ? C54 C55 C60 C59 -175.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.241 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.042 # Attachment '- cd201427.cif' data_cd201427 _database_code_depnum_ccdc_archive 'CCDC 789405' #TrackingRef '- cd201427.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H29 N O4' _chemical_formula_weight 503.57 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5777(9) _cell_length_b 12.4273(15) _cell_length_c 14.6322(18) _cell_angle_alpha 81.787(2) _cell_angle_beta 77.390(2) _cell_angle_gamma 80.671(2) _cell_volume 1318.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2369 _cell_measurement_theta_min 5.560 _cell_measurement_theta_max 53.163 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.415 _exptl_crystal_size_mid 0.360 _exptl_crystal_size_min 0.301 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3171 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6955 _diffrn_reflns_av_R_equivalents 0.0965 _diffrn_reflns_av_sigmaI/netI 0.0845 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4835 _reflns_number_gt 3402 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0940P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4835 _refine_ls_number_parameters 357 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1672 _refine_ls_wR_factor_gt 0.1536 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 1.025 _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 N1 N 0.2177(2) 0.67776(13) 0.59361(11) 0.0381(4) Uani 1 1 d . . . O1 O -0.0165(2) 0.67618(14) 0.72271(12) 0.0591(5) Uani 1 1 d . . . O2 O 0.4460(3) 0.32328(18) 0.98337(14) 0.0885(7) Uani 1 1 d . . . O3 O 0.2428(3) 0.27647(17) 0.91257(16) 0.0887(7) Uani 1 1 d . A . O4 O 0.0006(2) 0.40499(15) 0.73518(11) 0.0624(5) Uani 1 1 d . . . C1 C 0.1409(3) 0.64900(17) 0.68534(15) 0.0410(5) Uani 1 1 d . . . C2 C 0.4036(3) 0.63523(15) 0.57360(13) 0.0336(4) Uani 1 1 d . . . C3 C 0.5268(3) 0.64228(15) 0.48931(14) 0.0378(5) Uani 1 1 d . . . H3 H 0.4913 0.6782 0.4346 0.045 Uiso 1 1 calc R . . C4 C 0.7055(3) 0.59410(16) 0.48845(14) 0.0399(5) Uani 1 1 d . . . H4 H 0.7912 0.5982 0.4323 0.048 Uiso 1 1 calc R . . C5 C 0.7585(3) 0.54024(17) 0.56925(15) 0.0427(5) Uani 1 1 d . . . H5 H 0.8796 0.5098 0.5675 0.051 Uiso 1 1 calc R . . C6 C 0.6317(3) 0.53131(17) 0.65333(14) 0.0417(5) Uani 1 1 d . . . H6 H 0.6664 0.4935 0.7076 0.050 Uiso 1 1 calc R . . C7 C 0.4545(3) 0.57893(16) 0.65544(13) 0.0351(5) Uani 1 1 d . . . C8 C 0.2899(3) 0.58210(17) 0.73399(13) 0.0394(5) Uani 1 1 d . . . C9 C 0.2502(3) 0.46345(17) 0.77787(13) 0.0400(5) Uani 1 1 d . . . H9 H 0.3233 0.4110 0.7357 0.048 Uiso 1 1 calc R . . C10 C 0.3280(3) 0.4498(2) 0.86659(14) 0.0464(5) Uani 1 1 d . . . C11 C 0.3616(3) 0.5432(2) 0.88670(15) 0.0498(6) Uani 1 1 d . . . H11 H 0.4127 0.5490 0.9378 0.060 Uiso 1 1 calc R . . C12 C 0.3094(3) 0.63883(19) 0.81950(15) 0.0480(6) Uani 1 1 d . . . H12 H 0.1876 0.6734 0.8475 0.058 Uiso 1 1 calc R . . C13 C 0.4354(4) 0.7270(2) 0.79675(18) 0.0633(7) Uani 1 1 d . . . H13A H 0.4349 0.7581 0.8532 0.095 Uiso 1 1 calc R . . H13B H 0.3935 0.7835 0.7514 0.095 Uiso 1 1 calc R . . H13C H 0.5571 0.6950 0.7713 0.095 Uiso 1 1 calc R . . C14 C 0.3497(4) 0.3452(2) 0.92728(17) 0.0599(7) Uani 1 1 d . . . C15 C 0.2382(7) 0.1743(4) 0.9748(4) 0.1349(18) Uani 1 1 d D . . H15A H 0.2910 0.1130 0.9389 0.162 Uiso 0.566(19) 1 calc PR A 1 H15B H 0.3100 0.1745 1.0222 0.162 Uiso 0.566(19) 1 calc PR A 1 H15C H 0.1858 0.1880 1.0392 0.162 Uiso 0.434(19) 1 d PR A 2 H15D H 0.3598 0.1350 0.9692 0.162 Uiso 0.434(19) 1 d PR A 2 C16 C 0.0534(13) 0.1621(10) 1.0198(12) 0.168(6) Uani 0.566(19) 1 d PDU A 1 H16A H -0.0246 0.1854 0.9750 0.251 Uiso 0.566(19) 1 calc PR A 1 H16B H 0.0157 0.2061 1.0712 0.251 Uiso 0.566(19) 1 calc PR A 1 H16C H 0.0454 0.0864 1.0432 0.251 Uiso 0.566(19) 1 calc PR A 1 C16' C 0.102(3) 0.1174(14) 0.9503(17) 0.166(8) Uani 0.434(19) 1 d PDU A 2 H6D H 0.0542 0.0685 1.0036 0.254 Uiso 0.434(19) 1 calc PR A 2 H6E H 0.1583 0.0762 0.8983 0.254 Uiso 0.434(19) 1 calc PR A 2 H6F H 0.0043 0.1704 0.9330 0.254 Uiso 0.434(19) 1 calc PR A 2 C17 C 0.0493(3) 0.44649(19) 0.79331(15) 0.0466(6) Uani 1 1 d . . . C18 C -0.0814(4) 0.4802(2) 0.87936(17) 0.0672(7) Uani 1 1 d . . . H18A H -0.2026 0.4961 0.8667 0.101 Uiso 1 1 calc R . . H18B H -0.0485 0.5445 0.8972 0.101 Uiso 1 1 calc R . . H18C H -0.0775 0.4218 0.9298 0.101 Uiso 1 1 calc R . . C19 C 0.1121(3) 0.74451(17) 0.52757(16) 0.0446(5) Uani 1 1 d . . . H19A H -0.0108 0.7656 0.5617 0.054 Uiso 1 1 calc R . . H19B H 0.1036 0.6995 0.4801 0.054 Uiso 1 1 calc R . . C20 C 0.1896(3) 0.84719(17) 0.47835(17) 0.0460(6) Uani 1 1 d . . . C21 C 0.2383(3) 0.86261(19) 0.37908(18) 0.0525(6) Uani 1 1 d . . . C22 C 0.2241(4) 0.7845(2) 0.31920(19) 0.0635(7) Uani 1 1 d . . . H22 H 0.1851 0.7179 0.3464 0.076 Uiso 1 1 calc R . . C23 C 0.2656(5) 0.8045(3) 0.2242(2) 0.0853(9) Uani 1 1 d . . . H23 H 0.2550 0.7518 0.1872 0.102 Uiso 1 1 calc R . . C24 C 0.3247(5) 0.9041(4) 0.1810(3) 0.1043(12) Uani 1 1 d . . . H24 H 0.3512 0.9173 0.1156 0.125 Uiso 1 1 calc R . . C25 C 0.3431(5) 0.9798(3) 0.2323(3) 0.0942(11) Uani 1 1 d . . . H25 H 0.3836 1.0450 0.2022 0.113 Uiso 1 1 calc R . . C26 C 0.3019(4) 0.9630(2) 0.3335(2) 0.0691(8) Uani 1 1 d . . . C27 C 0.3186(4) 1.0418(2) 0.3875(3) 0.0763(9) Uani 1 1 d . . . H27 H 0.3624 1.1061 0.3574 0.092 Uiso 1 1 calc R . . C28 C 0.2728(3) 1.02844(19) 0.4845(3) 0.0674(8) Uani 1 1 d . . . C29 C 0.2882(4) 1.1106(2) 0.5393(4) 0.0904(12) Uani 1 1 d . . . H29 H 0.3349 1.1740 0.5088 0.108 Uiso 1 1 calc R . . C30 C 0.2377(5) 1.1002(3) 0.6336(4) 0.0977(13) Uani 1 1 d . . . H30 H 0.2508 1.1549 0.6678 0.117 Uiso 1 1 calc R . . C31 C 0.1642(4) 1.0045(2) 0.6800(3) 0.0825(10) Uani 1 1 d . . . H31 H 0.1266 0.9976 0.7452 0.099 Uiso 1 1 calc R . . C32 C 0.1472(4) 0.9226(2) 0.6315(2) 0.0634(7) Uani 1 1 d . . . H32 H 0.0985 0.8607 0.6641 0.076 Uiso 1 1 calc R . . C33 C 0.2025(3) 0.92997(18) 0.5316(2) 0.0530(6) 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 N1 0.0364(9) 0.0393(9) 0.0403(9) -0.0023(7) -0.0114(8) -0.0068(7) O1 0.0366(9) 0.0768(12) 0.0579(10) -0.0030(8) -0.0021(8) -0.0041(8) O2 0.1134(18) 0.0968(15) 0.0679(13) 0.0142(11) -0.0552(13) -0.0214(13) O3 0.0942(16) 0.0817(14) 0.0986(16) 0.0356(11) -0.0444(13) -0.0426(12) O4 0.0594(11) 0.0868(13) 0.0513(10) -0.0086(9) -0.0171(8) -0.0313(9) C1 0.0356(12) 0.0467(12) 0.0424(12) -0.0079(9) -0.0058(9) -0.0106(9) C2 0.0347(11) 0.0327(10) 0.0374(10) -0.0045(8) -0.0115(8) -0.0101(8) C3 0.0468(12) 0.0373(11) 0.0316(10) -0.0024(8) -0.0093(9) -0.0113(9) C4 0.0417(12) 0.0437(11) 0.0339(11) -0.0054(9) -0.0007(9) -0.0128(9) C5 0.0328(11) 0.0502(13) 0.0449(12) -0.0062(10) -0.0065(9) -0.0058(9) C6 0.0381(11) 0.0538(13) 0.0344(11) 0.0000(9) -0.0114(9) -0.0089(10) C7 0.0349(11) 0.0415(11) 0.0308(10) -0.0026(8) -0.0079(8) -0.0106(9) C8 0.0368(11) 0.0495(12) 0.0337(11) -0.0057(9) -0.0064(9) -0.0113(9) C9 0.0391(11) 0.0531(13) 0.0289(10) -0.0033(9) -0.0058(9) -0.0119(10) C10 0.0416(12) 0.0676(15) 0.0319(11) -0.0002(10) -0.0091(9) -0.0147(11) C11 0.0476(13) 0.0744(16) 0.0326(11) -0.0070(10) -0.0112(10) -0.0183(12) C12 0.0489(13) 0.0613(14) 0.0379(12) -0.0140(10) -0.0075(10) -0.0133(11) C13 0.0796(19) 0.0645(16) 0.0563(15) -0.0096(12) -0.0192(14) -0.0305(14) C14 0.0579(16) 0.0788(18) 0.0450(14) 0.0037(12) -0.0149(12) -0.0175(14) C15 0.134(4) 0.105(3) 0.165(4) 0.069(3) -0.052(3) -0.056(3) C16 0.149(7) 0.117(6) 0.176(9) 0.042(6) 0.061(6) -0.021(5) C16' 0.196(12) 0.136(9) 0.179(12) 0.026(7) -0.062(8) -0.069(8) C17 0.0456(13) 0.0612(14) 0.0350(11) 0.0031(10) -0.0091(10) -0.0191(11) C18 0.0490(15) 0.107(2) 0.0444(14) -0.0073(13) 0.0019(11) -0.0220(14) C19 0.0431(12) 0.0411(12) 0.0547(13) 0.0021(10) -0.0215(10) -0.0109(9) C20 0.0357(11) 0.0378(12) 0.0677(15) 0.0042(10) -0.0219(11) -0.0074(9) C21 0.0422(13) 0.0480(13) 0.0662(16) 0.0108(11) -0.0180(11) -0.0079(10) C22 0.0628(16) 0.0651(16) 0.0604(16) 0.0071(13) -0.0154(13) -0.0105(13) C23 0.090(2) 0.098(2) 0.0626(19) 0.0041(16) -0.0140(17) -0.0092(19) C24 0.102(3) 0.123(3) 0.072(2) 0.027(2) -0.005(2) -0.019(2) C25 0.075(2) 0.092(2) 0.099(3) 0.042(2) -0.007(2) -0.0230(19) C26 0.0477(15) 0.0598(16) 0.096(2) 0.0222(15) -0.0188(14) -0.0176(13) C27 0.0467(15) 0.0514(16) 0.128(3) 0.0227(17) -0.0245(17) -0.0168(12) C28 0.0399(14) 0.0386(14) 0.131(3) -0.0035(15) -0.0366(16) -0.0065(11) C29 0.0573(18) 0.0455(16) 0.184(4) -0.019(2) -0.054(2) -0.0076(13) C30 0.075(2) 0.065(2) 0.176(4) -0.052(2) -0.058(3) 0.0023(17) C31 0.0716(19) 0.070(2) 0.120(3) -0.0409(18) -0.0429(19) 0.0103(16) C32 0.0545(15) 0.0510(15) 0.092(2) -0.0190(14) -0.0306(15) 0.0028(12) C33 0.0371(12) 0.0391(13) 0.0878(19) -0.0043(12) -0.0274(12) -0.0025(10) _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 N1 C1 1.363(3) . ? N1 C2 1.404(2) . ? N1 C19 1.468(3) . ? O1 C1 1.214(3) . ? O2 C14 1.189(3) . ? O3 C14 1.336(3) . ? O3 C15 1.454(4) . ? O4 C17 1.204(3) . ? C1 C8 1.533(3) . ? C2 C3 1.376(3) . ? C2 C7 1.395(3) . ? C3 C4 1.388(3) . ? C3 H3 0.9300 . ? C4 C5 1.379(3) . ? C4 H4 0.9300 . ? C5 C6 1.389(3) . ? C5 H5 0.9300 . ? C6 C7 1.372(3) . ? C6 H6 0.9300 . ? C7 C8 1.500(3) . ? C8 C12 1.566(3) . ? C8 C9 1.570(3) . ? C9 C10 1.517(3) . ? C9 C17 1.534(3) . ? C9 H9 0.9800 . ? C10 C11 1.313(3) . ? C10 C14 1.473(3) . ? C11 C12 1.490(3) . ? C11 H11 0.9300 . ? C12 C13 1.522(3) . ? C12 H12 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C15 C16 1.434(9) . ? C15 C16' 1.472(12) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15C 0.9671 . ? C15 H15D 0.9623 . ? C16 H15C 1.2032 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C16' H6D 0.9600 . ? C16' H6E 0.9600 . ? C16' H6F 0.9600 . ? C17 C18 1.488(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.512(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C33 1.404(3) . ? C20 C21 1.411(3) . ? C21 C22 1.428(4) . ? C21 C26 1.432(3) . ? C22 C23 1.353(4) . ? C22 H22 0.9300 . ? C23 C24 1.401(5) . ? C23 H23 0.9300 . ? C24 C25 1.326(5) . ? C24 H24 0.9300 . ? C25 C26 1.436(5) . ? C25 H25 0.9300 . ? C26 C27 1.381(4) . ? C27 C28 1.377(4) . ? C27 H27 0.9300 . ? C28 C29 1.419(5) . ? C28 C33 1.438(4) . ? C29 C30 1.342(5) . ? C29 H29 0.9300 . ? C30 C31 1.416(5) . ? C30 H30 0.9300 . ? C31 C32 1.358(4) . ? C31 H31 0.9300 . ? C32 C33 1.424(4) . ? C32 H32 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 C1 N1 C2 111.20(16) . . ? C1 N1 C19 122.08(17) . . ? C2 N1 C19 126.71(17) . . ? C14 O3 C15 116.2(3) . . ? O1 C1 N1 125.6(2) . . ? O1 C1 C8 126.12(19) . . ? N1 C1 C8 108.21(17) . . ? C3 C2 C7 121.40(18) . . ? C3 C2 N1 129.15(18) . . ? C7 C2 N1 109.44(17) . . ? C2 C3 C4 117.92(18) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C5 C4 C3 121.25(19) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 119.25(19) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C2 119.94(18) . . ? C6 C7 C8 131.27(18) . . ? C2 C7 C8 108.78(17) . . ? C7 C8 C1 102.33(16) . . ? C7 C8 C12 114.08(16) . . ? C1 C8 C12 110.38(17) . . ? C7 C8 C9 111.48(16) . . ? C1 C8 C9 114.53(16) . . ? C12 C8 C9 104.38(16) . . ? C10 C9 C17 115.30(17) . . ? C10 C9 C8 101.67(16) . . ? C17 C9 C8 114.34(17) . . ? C10 C9 H9 108.4 . . ? C17 C9 H9 108.4 . . ? C8 C9 H9 108.4 . . ? C11 C10 C14 123.8(2) . . ? C11 C10 C9 112.3(2) . . ? C14 C10 C9 123.7(2) . . ? C10 C11 C12 113.23(19) . . ? C10 C11 H11 123.4 . . ? C12 C11 H11 123.4 . . ? C11 C12 C13 115.6(2) . . ? C11 C12 C8 102.22(17) . . ? C13 C12 C8 116.00(18) . . ? C11 C12 H12 107.5 . . ? C13 C12 H12 107.5 . . ? C8 C12 H12 107.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 O3 123.3(3) . . ? O2 C14 C10 125.9(3) . . ? O3 C14 C10 110.8(2) . . ? C16 C15 O3 109.9(5) . . ? C16 C15 C16' 48.2(8) . . ? O3 C15 C16' 106.1(6) . . ? C16 C15 H15A 109.7 . . ? O3 C15 H15A 109.7 . . ? C16' C15 H15A 66.2 . . ? C16 C15 H15B 109.7 . . ? O3 C15 H15B 109.7 . . ? C16' C15 H15B 143.2 . . ? H15A C15 H15B 108.2 . . ? C16 C15 H15C 56.2 . . ? O3 C15 H15C 110.9 . . ? C16' C15 H15C 102.9 . . ? H15A C15 H15C 139.4 . . ? H15B C15 H15C 56.3 . . ? C16 C15 H15D 140.8 . . ? O3 C15 H15D 109.2 . . ? C16' C15 H15D 116.0 . . ? H15A C15 H15D 52.4 . . ? H15B C15 H15D 58.9 . . ? H15C C15 H15D 111.5 . . ? C15 C16 H15C 41.9 . . ? C15 C16 H16A 109.5 . . ? H15C C16 H16A 138.7 . . ? C15 C16 H16B 109.5 . . ? H15C C16 H16B 70.7 . . ? C15 C16 H16C 109.5 . . ? H15C C16 H16C 108.9 . . ? C15 C16' H6D 109.5 . . ? C15 C16' H6E 109.5 . . ? H6D C16' H6E 109.5 . . ? C15 C16' H6F 109.5 . . ? H6D C16' H6F 109.5 . . ? H6E C16' H6F 109.5 . . ? O4 C17 C18 121.1(2) . . ? O4 C17 C9 118.9(2) . . ? C18 C17 C9 120.0(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 C20 115.02(17) . . ? N1 C19 H19A 108.5 . . ? C20 C19 H19A 108.5 . . ? N1 C19 H19B 108.5 . . ? C20 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? C33 C20 C21 120.1(2) . . ? C33 C20 C19 119.6(2) . . ? C21 C20 C19 120.2(2) . . ? C20 C21 C22 124.0(2) . . ? C20 C21 C26 119.4(2) . . ? C22 C21 C26 116.6(3) . . ? C23 C22 C21 122.0(3) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C22 C23 C24 120.4(4) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C25 C24 C23 120.8(3) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C24 C25 C26 121.3(3) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C27 C26 C21 119.3(3) . . ? C27 C26 C25 121.7(3) . . ? C21 C26 C25 118.9(3) . . ? C28 C27 C26 122.3(3) . . ? C28 C27 H27 118.8 . . ? C26 C27 H27 118.8 . . ? C27 C28 C29 121.8(3) . . ? C27 C28 C33 119.3(3) . . ? C29 C28 C33 118.9(3) . . ? C30 C29 C28 122.3(3) . . ? C30 C29 H29 118.8 . . ? C28 C29 H29 118.8 . . ? C29 C30 C31 119.0(3) . . ? C29 C30 H30 120.5 . . ? C31 C30 H30 120.5 . . ? C32 C31 C30 121.5(4) . . ? C32 C31 H31 119.3 . . ? C30 C31 H31 119.3 . . ? C31 C32 C33 121.1(3) . . ? C31 C32 H32 119.5 . . ? C33 C32 H32 119.5 . . ? C20 C33 C32 123.3(2) . . ? C20 C33 C28 119.4(3) . . ? C32 C33 C28 117.2(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 C2 N1 C1 O1 178.33(19) . . . . ? C19 N1 C1 O1 -1.9(3) . . . . ? C2 N1 C1 C8 1.4(2) . . . . ? C19 N1 C1 C8 -178.80(17) . . . . ? C1 N1 C2 C3 177.41(19) . . . . ? C19 N1 C2 C3 -2.4(3) . . . . ? C1 N1 C2 C7 -1.9(2) . . . . ? C19 N1 C2 C7 178.30(18) . . . . ? C7 C2 C3 C4 -1.8(3) . . . . ? N1 C2 C3 C4 179.00(18) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 C6 1.3(3) . . . . ? C4 C5 C6 C7 -1.6(3) . . . . ? C5 C6 C7 C2 0.2(3) . . . . ? C5 C6 C7 C8 179.32(19) . . . . ? C3 C2 C7 C6 1.5(3) . . . . ? N1 C2 C7 C6 -179.11(17) . . . . ? C3 C2 C7 C8 -177.79(16) . . . . ? N1 C2 C7 C8 1.6(2) . . . . ? C6 C7 C8 C1 -179.9(2) . . . . ? C2 C7 C8 C1 -0.7(2) . . . . ? C6 C7 C8 C12 60.9(3) . . . . ? C2 C7 C8 C12 -119.93(19) . . . . ? C6 C7 C8 C9 -57.1(3) . . . . ? C2 C7 C8 C9 122.15(18) . . . . ? O1 C1 C8 C7 -177.3(2) . . . . ? N1 C1 C8 C7 -0.4(2) . . . . ? O1 C1 C8 C12 -55.5(3) . . . . ? N1 C1 C8 C12 121.38(18) . . . . ? O1 C1 C8 C9 61.9(3) . . . . ? N1 C1 C8 C9 -121.18(18) . . . . ? C7 C8 C9 C10 100.91(18) . . . . ? C1 C8 C9 C10 -143.50(18) . . . . ? C12 C8 C9 C10 -22.7(2) . . . . ? C7 C8 C9 C17 -134.17(18) . . . . ? C1 C8 C9 C17 -18.6(2) . . . . ? C12 C8 C9 C17 102.21(19) . . . . ? C17 C9 C10 C11 -110.5(2) . . . . ? C8 C9 C10 C11 13.8(2) . . . . ? C17 C9 C10 C14 65.0(3) . . . . ? C8 C9 C10 C14 -170.8(2) . . . . ? C14 C10 C11 C12 -173.6(2) . . . . ? C9 C10 C11 C12 1.8(3) . . . . ? C10 C11 C12 C13 -143.6(2) . . . . ? C10 C11 C12 C8 -16.7(2) . . . . ? C7 C8 C12 C11 -98.1(2) . . . . ? C1 C8 C12 C11 147.32(17) . . . . ? C9 C8 C12 C11 23.8(2) . . . . ? C7 C8 C12 C13 28.6(3) . . . . ? C1 C8 C12 C13 -86.0(2) . . . . ? C9 C8 C12 C13 150.5(2) . . . . ? C15 O3 C14 O2 4.8(5) . . . . ? C15 O3 C14 C10 -174.2(3) . . . . ? C11 C10 C14 O2 -23.7(4) . . . . ? C9 C10 C14 O2 161.3(3) . . . . ? C11 C10 C14 O3 155.2(2) . . . . ? C9 C10 C14 O3 -19.8(3) . . . . ? C14 O3 C15 C16 124.8(10) . . . . ? C14 O3 C15 C16' 175.5(12) . . . . ? C10 C9 C17 O4 -145.1(2) . . . . ? C8 C9 C17 O4 97.6(2) . . . . ? C10 C9 C17 C18 34.4(3) . . . . ? C8 C9 C17 C18 -83.0(3) . . . . ? C1 N1 C19 C20 125.1(2) . . . . ? C2 N1 C19 C20 -55.1(3) . . . . ? N1 C19 C20 C33 -63.1(3) . . . . ? N1 C19 C20 C21 120.7(2) . . . . ? C33 C20 C21 C22 -178.0(2) . . . . ? C19 C20 C21 C22 -1.8(3) . . . . ? C33 C20 C21 C26 0.4(3) . . . . ? C19 C20 C21 C26 176.6(2) . . . . ? C20 C21 C22 C23 177.4(3) . . . . ? C26 C21 C22 C23 -1.0(4) . . . . ? C21 C22 C23 C24 0.0(5) . . . . ? C22 C23 C24 C25 0.9(6) . . . . ? C23 C24 C25 C26 -0.6(6) . . . . ? C20 C21 C26 C27 1.6(4) . . . . ? C22 C21 C26 C27 -180.0(2) . . . . ? C20 C21 C26 C25 -177.2(2) . . . . ? C22 C21 C26 C25 1.2(4) . . . . ? C24 C25 C26 C27 -179.2(3) . . . . ? C24 C25 C26 C21 -0.5(5) . . . . ? C21 C26 C27 C28 -1.3(4) . . . . ? C25 C26 C27 C28 177.4(3) . . . . ? C26 C27 C28 C29 -179.1(2) . . . . ? C26 C27 C28 C33 -0.9(4) . . . . ? C27 C28 C29 C30 177.5(3) . . . . ? C33 C28 C29 C30 -0.7(4) . . . . ? C28 C29 C30 C31 -0.9(5) . . . . ? C29 C30 C31 C32 1.3(5) . . . . ? C30 C31 C32 C33 -0.1(4) . . . . ? C21 C20 C33 C32 176.7(2) . . . . ? C19 C20 C33 C32 0.5(3) . . . . ? C21 C20 C33 C28 -2.6(3) . . . . ? C19 C20 C33 C28 -178.76(19) . . . . ? C31 C32 C33 C20 179.3(2) . . . . ? C31 C32 C33 C28 -1.4(3) . . . . ? C27 C28 C33 C20 2.8(3) . . . . ? C29 C28 C33 C20 -178.9(2) . . . . ? C27 C28 C33 C32 -176.5(2) . . . . ? C29 C28 C33 C32 1.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.277 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.054 # Attachment '- cd201470.cif' data_cd201470 _database_code_depnum_ccdc_archive 'CCDC 792765' #TrackingRef '- cd201470.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H16 Br N O2' _chemical_formula_weight 418.28 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 8.2650(17) _cell_length_b 13.415(3) _cell_length_c 16.413(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.032(4) _cell_angle_gamma 90.00 _cell_volume 1818.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3397 _cell_measurement_theta_min 4.967 _cell_measurement_theta_max 53.953 _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.401 _exptl_crystal_size_mid 0.256 _exptl_crystal_size_min 0.147 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 2.278 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.48225 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9725 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3572 _reflns_number_gt 2619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3572 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 Br1 Br 0.91041(4) 0.23605(2) 0.239103(16) 0.06374(15) Uani 1 1 d . . . N1 N 0.9175(2) 0.36429(15) 0.54645(11) 0.0408(5) Uani 1 1 d . . . O1 O 0.8706(2) 0.45942(15) 0.65938(9) 0.0578(5) Uani 1 1 d . . . O2 O 0.5371(2) 0.64022(13) 0.43329(9) 0.0505(5) Uani 1 1 d . . . C1 C 0.8502(3) 0.44198(19) 0.58709(14) 0.0424(6) Uani 1 1 d . . . C2 C 0.8706(3) 0.36783(18) 0.46364(13) 0.0379(6) Uani 1 1 d . . . C3 C 0.9145(3) 0.3027(2) 0.40324(14) 0.0428(6) Uani 1 1 d . . . H3 H 0.9825 0.2487 0.4143 0.051 Uiso 1 1 calc R . . C4 C 0.8524(3) 0.3216(2) 0.32542(14) 0.0455(6) Uani 1 1 d . . . C5 C 0.7508(3) 0.4006(2) 0.30741(14) 0.0475(6) Uani 1 1 d . . . H5 H 0.7116 0.4106 0.2542 0.057 Uiso 1 1 calc R . . C6 C 0.7075(3) 0.46483(19) 0.36867(13) 0.0435(6) Uani 1 1 d . . . H6 H 0.6382 0.5179 0.3570 0.052 Uiso 1 1 calc R . . C7 C 0.7682(3) 0.44973(17) 0.44790(12) 0.0356(5) Uani 1 1 d . . . C8 C 0.7503(3) 0.50148(18) 0.52517(13) 0.0364(5) Uani 1 1 d . . . C9 C 0.6758(3) 0.58325(18) 0.55194(13) 0.0411(6) Uani 1 1 d . . . H9 H 0.6883 0.5958 0.6075 0.049 Uiso 1 1 calc R . . C10 C 0.5769(3) 0.65561(18) 0.50516(13) 0.0392(6) Uani 1 1 d . . . C11 C 0.5253(3) 0.74893(18) 0.54553(14) 0.0388(6) Uani 1 1 d . . . C12 C 0.5561(4) 0.7705(2) 0.62760(16) 0.0541(7) Uani 1 1 d . . . H12 H 0.6134 0.7253 0.6605 0.065 Uiso 1 1 calc R . . C13 C 0.5023(4) 0.8584(2) 0.66037(16) 0.0632(8) Uani 1 1 d . . . H13 H 0.5234 0.8719 0.7153 0.076 Uiso 1 1 calc R . . C14 C 0.4188(4) 0.9255(2) 0.61339(19) 0.0634(8) Uani 1 1 d . . . H14 H 0.3835 0.9848 0.6361 0.076 Uiso 1 1 calc R . . C15 C 0.3867(4) 0.9058(2) 0.53269(18) 0.0643(8) Uani 1 1 d . . . H15 H 0.3288 0.9516 0.5007 0.077 Uiso 1 1 calc R . . C16 C 0.4397(3) 0.8187(2) 0.49878(16) 0.0524(7) Uani 1 1 d . . . H16 H 0.4179 0.8063 0.4437 0.063 Uiso 1 1 calc R . . C17 C 1.0391(3) 0.2975(2) 0.58318(15) 0.0455(6) Uani 1 1 d . . . H17A H 1.0901 0.3308 0.6298 0.055 Uiso 1 1 calc R . . H17B H 1.1220 0.2858 0.5439 0.055 Uiso 1 1 calc R . . C18 C 0.9758(3) 0.19817(19) 0.61063(13) 0.0396(6) Uani 1 1 d . . . C19 C 1.0509(3) 0.1111(2) 0.58779(15) 0.0531(7) Uani 1 1 d . . . H19 H 1.1365 0.1137 0.5526 0.064 Uiso 1 1 calc R . . C20 C 0.9997(4) 0.0204(2) 0.6168(2) 0.0647(8) Uani 1 1 d . . . H20 H 1.0516 -0.0377 0.6013 0.078 Uiso 1 1 calc R . . C21 C 0.8729(4) 0.0152(2) 0.66838(18) 0.0644(8) Uani 1 1 d . . . H21 H 0.8388 -0.0461 0.6880 0.077 Uiso 1 1 calc R . . C22 C 0.7969(3) 0.1015(2) 0.69070(16) 0.0562(7) Uani 1 1 d . . . H22 H 0.7103 0.0986 0.7253 0.067 Uiso 1 1 calc R . . C23 C 0.8482(3) 0.1920(2) 0.66227(14) 0.0470(6) Uani 1 1 d . . . H23 H 0.7961 0.2500 0.6781 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0717(2) 0.0705(2) 0.0495(2) -0.01939(14) 0.00969(14) 0.00387(16) N1 0.0442(12) 0.0441(12) 0.0340(10) 0.0059(9) -0.0019(9) 0.0033(10) O1 0.0785(14) 0.0640(13) 0.0305(9) 0.0020(8) -0.0055(8) 0.0132(10) O2 0.0623(12) 0.0559(11) 0.0330(9) -0.0014(8) -0.0033(8) 0.0065(9) C1 0.0491(15) 0.0448(15) 0.0332(12) 0.0052(11) 0.0022(10) -0.0033(12) C2 0.0375(13) 0.0428(14) 0.0334(12) 0.0057(10) 0.0037(10) -0.0067(11) C3 0.0448(14) 0.0392(14) 0.0448(14) 0.0034(11) 0.0063(11) -0.0012(12) C4 0.0515(16) 0.0481(16) 0.0373(13) -0.0073(12) 0.0084(11) -0.0057(13) C5 0.0571(16) 0.0539(17) 0.0312(12) -0.0009(12) 0.0000(11) -0.0017(14) C6 0.0513(15) 0.0458(15) 0.0332(12) 0.0030(11) -0.0006(11) 0.0019(12) C7 0.0376(13) 0.0373(14) 0.0322(12) 0.0045(10) 0.0029(9) -0.0034(10) C8 0.0379(13) 0.0404(14) 0.0310(11) 0.0051(10) 0.0019(10) -0.0039(11) C9 0.0475(15) 0.0463(15) 0.0294(11) 0.0024(11) 0.0010(10) -0.0027(12) C10 0.0387(14) 0.0449(15) 0.0343(13) 0.0049(11) 0.0038(10) -0.0052(11) C11 0.0375(14) 0.0427(15) 0.0361(13) 0.0004(11) 0.0016(10) -0.0024(11) C12 0.070(2) 0.0530(17) 0.0382(14) -0.0040(12) -0.0068(13) 0.0109(14) C13 0.079(2) 0.064(2) 0.0469(16) -0.0129(15) -0.0054(15) 0.0028(17) C14 0.0665(19) 0.0522(18) 0.0717(19) -0.0167(16) 0.0026(15) 0.0090(15) C15 0.072(2) 0.0569(19) 0.0632(18) 0.0001(15) -0.0101(15) 0.0184(16) C16 0.0540(17) 0.0552(18) 0.0474(15) -0.0012(13) -0.0075(13) 0.0073(14) C17 0.0404(14) 0.0505(16) 0.0452(14) 0.0077(12) -0.0030(11) 0.0012(12) C18 0.0406(14) 0.0470(15) 0.0306(12) 0.0033(11) -0.0065(10) 0.0016(12) C19 0.0495(16) 0.0605(19) 0.0494(15) -0.0015(14) 0.0009(12) 0.0078(14) C20 0.066(2) 0.0459(18) 0.082(2) -0.0026(16) -0.0080(17) 0.0061(16) C21 0.067(2) 0.054(2) 0.070(2) 0.0171(16) -0.0115(16) -0.0106(16) C22 0.0569(17) 0.062(2) 0.0496(15) 0.0134(14) 0.0010(13) -0.0068(15) C23 0.0499(16) 0.0516(16) 0.0395(13) 0.0022(12) -0.0001(11) 0.0012(13) _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 Br1 C4 1.898(2) . ? N1 C1 1.366(3) . ? N1 C2 1.401(3) . ? N1 C17 1.461(3) . ? O1 C1 1.215(3) . ? O2 C10 1.231(3) . ? C1 C8 1.514(3) . ? C2 C3 1.380(3) . ? C2 C7 1.405(3) . ? C3 C4 1.383(3) . ? C3 H3 0.9300 . ? C4 C5 1.377(4) . ? C5 C6 1.381(3) . ? C5 H5 0.9300 . ? C6 C7 1.392(3) . ? C6 H6 0.9300 . ? C7 C8 1.458(3) . ? C8 C9 1.340(3) . ? C9 C10 1.468(3) . ? C9 H9 0.9300 . ? C10 C11 1.486(3) . ? C11 C16 1.388(4) . ? C11 C12 1.393(3) . ? C12 C13 1.376(4) . ? C12 H12 0.9300 . ? C13 C14 1.358(4) . ? C13 H13 0.9300 . ? C14 C15 1.367(4) . ? C14 H14 0.9300 . ? C15 C16 1.373(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.506(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C23 1.379(3) . ? C18 C19 1.380(4) . ? C19 C20 1.379(4) . ? C19 H19 0.9300 . ? C20 C21 1.372(4) . ? C20 H20 0.9300 . ? C21 C22 1.373(4) . ? C21 H21 0.9300 . ? C22 C23 1.373(4) . ? C22 H22 0.9300 . ? C23 H23 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 C1 N1 C2 110.16(19) . . ? C1 N1 C17 123.5(2) . . ? C2 N1 C17 125.7(2) . . ? O1 C1 N1 125.4(2) . . ? O1 C1 C8 127.4(2) . . ? N1 C1 C8 107.22(19) . . ? C3 C2 N1 127.2(2) . . ? C3 C2 C7 122.4(2) . . ? N1 C2 C7 110.4(2) . . ? C2 C3 C4 116.6(2) . . ? C2 C3 H3 121.7 . . ? C4 C3 H3 121.7 . . ? C5 C4 C3 122.9(2) . . ? C5 C4 Br1 118.24(18) . . ? C3 C4 Br1 118.9(2) . . ? C4 C5 C6 119.7(2) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C7 119.7(2) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C2 118.7(2) . . ? C6 C7 C8 134.3(2) . . ? C2 C7 C8 106.96(19) . . ? C9 C8 C7 137.5(2) . . ? C9 C8 C1 117.2(2) . . ? C7 C8 C1 105.2(2) . . ? C8 C9 C10 128.6(2) . . ? C8 C9 H9 115.7 . . ? C10 C9 H9 115.7 . . ? O2 C10 C9 121.0(2) . . ? O2 C10 C11 119.8(2) . . ? C9 C10 C11 119.1(2) . . ? C16 C11 C12 117.8(2) . . ? C16 C11 C10 118.1(2) . . ? C12 C11 C10 124.1(2) . . ? C13 C12 C11 120.4(3) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 120.7(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 120.0(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 120.2(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.9(2) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? N1 C17 C18 115.2(2) . . ? N1 C17 H17A 108.5 . . ? C18 C17 H17A 108.5 . . ? N1 C17 H17B 108.5 . . ? C18 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C23 C18 C19 118.5(3) . . ? C23 C18 C17 121.2(3) . . ? C19 C18 C17 120.2(2) . . ? C20 C19 C18 120.4(3) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 120.6(3) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 119.2(3) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C21 C22 C23 120.4(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C18 120.9(3) . . ? C22 C23 H23 119.6 . . ? C18 C23 H23 119.6 . . ? 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 C2 N1 C1 O1 -178.9(2) . . . . ? C17 N1 C1 O1 -7.3(4) . . . . ? C2 N1 C1 C8 0.1(3) . . . . ? C17 N1 C1 C8 171.7(2) . . . . ? C1 N1 C2 C3 179.6(2) . . . . ? C17 N1 C2 C3 8.2(4) . . . . ? C1 N1 C2 C7 -0.3(3) . . . . ? C17 N1 C2 C7 -171.7(2) . . . . ? N1 C2 C3 C4 180.0(2) . . . . ? C7 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? C2 C3 C4 Br1 179.10(18) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? Br1 C4 C5 C6 -179.35(19) . . . . ? C4 C5 C6 C7 0.6(4) . . . . ? C5 C6 C7 C2 -1.1(4) . . . . ? C5 C6 C7 C8 179.3(2) . . . . ? C3 C2 C7 C6 0.8(3) . . . . ? N1 C2 C7 C6 -179.3(2) . . . . ? C3 C2 C7 C8 -179.5(2) . . . . ? N1 C2 C7 C8 0.4(3) . . . . ? C6 C7 C8 C9 -2.4(5) . . . . ? C2 C7 C8 C9 177.9(3) . . . . ? C6 C7 C8 C1 179.3(3) . . . . ? C2 C7 C8 C1 -0.4(2) . . . . ? O1 C1 C8 C9 0.5(4) . . . . ? N1 C1 C8 C9 -178.5(2) . . . . ? O1 C1 C8 C7 179.2(2) . . . . ? N1 C1 C8 C7 0.2(3) . . . . ? C7 C8 C9 C10 -0.4(5) . . . . ? C1 C8 C9 C10 177.8(2) . . . . ? C8 C9 C10 O2 8.4(4) . . . . ? C8 C9 C10 C11 -171.3(2) . . . . ? O2 C10 C11 C16 -3.3(4) . . . . ? C9 C10 C11 C16 176.4(2) . . . . ? O2 C10 C11 C12 176.1(2) . . . . ? C9 C10 C11 C12 -4.1(4) . . . . ? C16 C11 C12 C13 0.2(4) . . . . ? C10 C11 C12 C13 -179.3(3) . . . . ? C11 C12 C13 C14 -0.2(5) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C13 C14 C15 C16 -0.5(5) . . . . ? C14 C15 C16 C11 0.5(5) . . . . ? C12 C11 C16 C15 -0.3(4) . . . . ? C10 C11 C16 C15 179.1(3) . . . . ? C1 N1 C17 C18 100.9(3) . . . . ? C2 N1 C17 C18 -88.8(3) . . . . ? N1 C17 C18 C23 -53.5(3) . . . . ? N1 C17 C18 C19 129.9(2) . . . . ? C23 C18 C19 C20 -0.6(4) . . . . ? C17 C18 C19 C20 176.0(2) . . . . ? C18 C19 C20 C21 0.4(4) . . . . ? C19 C20 C21 C22 0.2(4) . . . . ? C20 C21 C22 C23 -0.5(4) . . . . ? C21 C22 C23 C18 0.3(4) . . . . ? C19 C18 C23 C22 0.2(4) . . . . ? C17 C18 C23 C22 -176.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.634 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.057