# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Chun-Jiang Wang' _publ_contact_author_email CJWANG@WHU.EDU.CN _publ_section_title ; Exo-Selective Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with Alkylidene Malonates Catalyzed by AgOAc/TF-BiphamPhos ; loop_ _publ_author_name 'Chun-Jiang Wang' 'He Huang' 'Tang-Lin Liu' 'Zhi-Yong Xue' # Attachment '90605xzy1_0m.cif' data_90605xzy1_0m _database_code_depnum_ccdc_archive 'CCDC 739450' #TrackingRef '90605xzy1_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_absolute_configuration 2S,3S,5S _chemical_formula_sum 'C29 H36 Br N O7' _chemical_formula_weight 590.50 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.7742(8) _cell_length_b 15.7902(13) _cell_length_c 18.9829(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2929.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 176 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 1.448 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5883 _exptl_absorpt_correction_T_max 0.6388 _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 ? _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 16920 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5717 _reflns_number_gt 4283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.5312P] 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 0.0100(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(9) _refine_ls_number_reflns 5717 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1127 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.57599(6) 0.84707(3) 0.79853(3) 0.0826(2) Uani 1 1 d . . . C1 C 0.6335(4) 0.7474(2) 0.75108(19) 0.0541(9) Uani 1 1 d . . . C2 C 0.7535(4) 0.7468(2) 0.7130(2) 0.0573(9) Uani 1 1 d . . . H2 H 0.8061 0.7957 0.7091 0.069 Uiso 1 1 calc R . . C3 C 0.7948(4) 0.6727(2) 0.68080(18) 0.0526(9) Uani 1 1 d . . . H3 H 0.8759 0.6723 0.6552 0.063 Uiso 1 1 calc R . . C4 C 0.7186(3) 0.5986(2) 0.68542(16) 0.0413(7) Uani 1 1 d . . . C5 C 0.5979(3) 0.6022(2) 0.72435(18) 0.0516(8) Uani 1 1 d . . . H5 H 0.5439 0.5539 0.7284 0.062 Uiso 1 1 calc R . . C6 C 0.5568(4) 0.6760(3) 0.7570(2) 0.0598(10) Uani 1 1 d . . . H6 H 0.4764 0.6769 0.7832 0.072 Uiso 1 1 calc R . . C7 C 0.7610(3) 0.5150(2) 0.65323(16) 0.0390(7) Uani 1 1 d . . . H7 H 0.6930 0.4720 0.6658 0.047 Uiso 1 1 calc R . . C8 C 0.9025(3) 0.4861(2) 0.68072(16) 0.0447(8) Uani 1 1 d . . . H8 H 0.9251 0.5207 0.7220 0.054 Uiso 1 1 calc R . . C9 C 0.9370(3) 0.5319(2) 0.56122(16) 0.0437(7) Uani 1 1 d . . . H9 H 0.9485 0.5935 0.5587 0.052 Uiso 1 1 calc R . . C10 C 0.7791(3) 0.51508(19) 0.57162(15) 0.0353(7) Uani 1 1 d . . . C11 C 0.9095(4) 0.3938(3) 0.7027(2) 0.0633(10) Uani 1 1 d . . . C12 C 0.8061(7) 0.2880(4) 0.7715(5) 0.144(3) Uani 1 1 d . . . H12A H 0.7714 0.2532 0.7341 0.216 Uiso 1 1 calc R . . H12B H 0.7463 0.2841 0.8115 0.216 Uiso 1 1 calc R . . H12C H 0.8959 0.2688 0.7845 0.216 Uiso 1 1 calc R . . C13 C 0.6925(3) 0.5827(2) 0.53565(17) 0.0414(7) Uani 1 1 d . . . C14 C 0.4529(3) 0.6283(2) 0.5276(2) 0.0566(9) Uani 1 1 d . . . C15 C 0.4402(6) 0.6223(4) 0.4487(3) 0.0957(16) Uani 1 1 d . . . H15A H 0.5225 0.6430 0.4272 0.143 Uiso 1 1 calc R . . H15B H 0.3639 0.6557 0.4332 0.143 Uiso 1 1 calc R . . H15C H 0.4261 0.5642 0.4355 0.143 Uiso 1 1 calc R . . C16 C 0.4804(5) 0.7166(3) 0.5531(3) 0.0886(15) Uani 1 1 d . . . H16A H 0.5049 0.7150 0.6020 0.133 Uiso 1 1 calc R . . H16B H 0.3997 0.7505 0.5471 0.133 Uiso 1 1 calc R . . H16C H 0.5542 0.7407 0.5264 0.133 Uiso 1 1 calc R . . C17 C 0.3270(4) 0.5911(4) 0.5629(3) 0.0890(16) Uani 1 1 d . . . H17A H 0.3160 0.5333 0.5485 0.133 Uiso 1 1 calc R . . H17B H 0.2477 0.6231 0.5494 0.133 Uiso 1 1 calc R . . H17C H 0.3379 0.5936 0.6131 0.133 Uiso 1 1 calc R . . C18 C 0.7394(3) 0.4284(2) 0.54255(15) 0.0361(7) Uani 1 1 d . . . C19 C 0.6424(3) 0.3619(2) 0.43635(17) 0.0454(8) Uani 1 1 d . . . C20 C 0.5121(4) 0.3337(3) 0.4719(2) 0.0622(10) Uani 1 1 d . . . H20A H 0.5335 0.3080 0.5164 0.093 Uiso 1 1 calc R . . H20B H 0.4659 0.2933 0.4425 0.093 Uiso 1 1 calc R . . H20C H 0.4538 0.3818 0.4794 0.093 Uiso 1 1 calc R . . C21 C 0.7470(4) 0.2920(2) 0.4299(2) 0.0592(9) Uani 1 1 d . . . H21A H 0.8312 0.3149 0.4121 0.089 Uiso 1 1 calc R . . H21B H 0.7137 0.2495 0.3981 0.089 Uiso 1 1 calc R . . H21C H 0.7627 0.2672 0.4753 0.089 Uiso 1 1 calc R . . C22 C 0.6149(5) 0.4014(3) 0.3652(2) 0.0696(11) Uani 1 1 d . . . H22A H 0.5433 0.4427 0.3696 0.104 Uiso 1 1 calc R . . H22B H 0.5873 0.3582 0.3326 0.104 Uiso 1 1 calc R . . H22C H 0.6966 0.4284 0.3484 0.104 Uiso 1 1 calc R . . C23 C 1.0061(3) 0.4957(2) 0.49671(17) 0.0407(7) Uani 1 1 d . . . C24 C 1.0571(3) 0.4137(2) 0.49404(19) 0.0503(8) Uani 1 1 d . . . H24 H 1.0411 0.3773 0.5317 0.060 Uiso 1 1 calc R . . C25 C 1.1305(3) 0.3849(2) 0.4373(2) 0.0545(9) Uani 1 1 d . . . H25 H 1.1640 0.3298 0.4370 0.065 Uiso 1 1 calc R . . C26 C 1.1546(3) 0.4376(2) 0.38080(19) 0.0492(8) Uani 1 1 d . . . C27 C 1.1024(4) 0.5178(2) 0.38135(19) 0.0538(9) Uani 1 1 d . . . H27 H 1.1167 0.5535 0.3431 0.065 Uiso 1 1 calc R . . C28 C 1.0283(3) 0.5459(2) 0.43884(18) 0.0494(8) Uani 1 1 d . . . H28 H 0.9926 0.6005 0.4383 0.059 Uiso 1 1 calc R . . C29 C 1.2763(4) 0.4563(3) 0.27468(19) 0.0638(11) Uani 1 1 d . . . H29A H 1.1980 0.4777 0.2499 0.096 Uiso 1 1 calc R . . H29B H 1.3335 0.4253 0.2426 0.096 Uiso 1 1 calc R . . H29C H 1.3271 0.5027 0.2943 0.096 Uiso 1 1 calc R . . N1 N 1.0010(3) 0.5046(2) 0.62668(16) 0.0645(9) Uani 1 1 d . . . H1 H 1.0879 0.5000 0.6323 0.077 Uiso 1 1 calc R . . O1 O 0.9955(4) 0.3448(2) 0.6825(2) 0.1033(11) Uani 1 1 d . . . O2 O 0.8135(3) 0.3753(2) 0.74796(18) 0.0861(10) Uani 1 1 d . . . O3 O 0.7360(3) 0.63851(16) 0.49955(14) 0.0622(7) Uani 1 1 d . . . O4 O 0.5615(2) 0.56955(13) 0.55190(12) 0.0439(5) Uani 1 1 d . . . O5 O 0.7444(3) 0.36419(15) 0.57658(12) 0.0532(6) Uani 1 1 d . . . O6 O 0.7008(2) 0.43471(13) 0.47593(11) 0.0408(5) Uani 1 1 d . . . O7 O 1.2340(3) 0.40359(18) 0.32792(14) 0.0675(7) 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 Br1 0.1132(4) 0.0645(3) 0.0699(3) 0.0002(2) 0.0119(3) 0.0300(2) C1 0.061(2) 0.059(2) 0.042(2) 0.0047(17) 0.0024(17) 0.0136(19) C2 0.065(2) 0.051(2) 0.056(2) -0.0008(18) 0.0016(19) -0.0085(17) C3 0.0497(19) 0.058(2) 0.050(2) -0.0057(16) 0.0083(16) -0.0073(17) C4 0.0362(16) 0.0539(19) 0.0339(18) 0.0001(14) -0.0042(13) -0.0052(14) C5 0.0426(18) 0.058(2) 0.054(2) -0.0006(16) 0.0087(16) -0.0052(16) C6 0.0477(19) 0.073(3) 0.058(2) 0.0049(19) 0.0147(18) 0.0083(19) C7 0.0331(15) 0.0455(18) 0.0385(17) 0.0030(13) -0.0017(13) -0.0050(13) C8 0.0362(16) 0.059(2) 0.0385(18) -0.0010(14) -0.0075(14) -0.0046(14) C9 0.0292(14) 0.0597(19) 0.0423(18) 0.0009(15) -0.0004(14) -0.0114(14) C10 0.0283(14) 0.0404(16) 0.0372(16) 0.0027(13) -0.0043(13) -0.0044(12) C11 0.050(2) 0.071(2) 0.069(3) 0.005(2) -0.018(2) -0.001(2) C12 0.125(5) 0.110(5) 0.197(8) 0.092(5) -0.042(5) -0.031(4) C13 0.0384(17) 0.0437(18) 0.0422(18) 0.0012(15) -0.0026(14) -0.0070(14) C14 0.043(2) 0.061(2) 0.066(2) 0.0051(18) -0.0138(17) 0.0100(16) C15 0.089(3) 0.122(4) 0.076(3) 0.004(3) -0.036(3) 0.030(3) C16 0.078(3) 0.059(3) 0.129(4) -0.009(3) -0.032(3) 0.023(2) C17 0.041(2) 0.103(4) 0.123(4) 0.023(3) -0.005(2) 0.004(2) C18 0.0261(14) 0.0453(18) 0.0370(17) 0.0063(14) -0.0030(13) -0.0012(12) C19 0.0470(18) 0.052(2) 0.0372(18) -0.0059(15) -0.0057(14) -0.0058(15) C20 0.0475(19) 0.069(3) 0.070(3) -0.014(2) -0.0041(18) -0.0149(18) C21 0.066(2) 0.059(2) 0.053(2) -0.0095(18) -0.0007(18) 0.0002(18) C22 0.088(3) 0.076(3) 0.045(2) -0.0040(19) -0.021(2) 0.004(2) C23 0.0273(14) 0.0493(18) 0.0457(19) 0.0035(15) -0.0017(14) -0.0063(13) C24 0.0421(18) 0.056(2) 0.053(2) 0.0117(16) 0.0065(16) -0.0010(16) C25 0.0443(18) 0.049(2) 0.070(3) 0.0043(19) 0.0061(18) 0.0063(15) C26 0.0395(18) 0.061(2) 0.047(2) -0.0066(17) 0.0035(15) -0.0040(16) C27 0.062(2) 0.058(2) 0.0409(19) 0.0065(16) 0.0073(17) -0.0063(18) C28 0.051(2) 0.0445(19) 0.053(2) 0.0027(16) 0.0014(16) 0.0030(15) C29 0.044(2) 0.099(3) 0.049(2) -0.007(2) 0.0085(17) -0.0041(19) N1 0.0341(14) 0.113(3) 0.0461(18) -0.0006(18) -0.0046(14) -0.0050(16) O1 0.088(2) 0.091(2) 0.131(3) 0.002(2) -0.030(2) 0.035(2) O2 0.0767(19) 0.088(2) 0.094(2) 0.0405(18) -0.0066(18) -0.0048(16) O3 0.0536(14) 0.0563(15) 0.0767(17) 0.0284(14) 0.0050(13) -0.0071(12) O4 0.0319(10) 0.0452(12) 0.0545(13) 0.0071(10) -0.0066(10) -0.0013(9) O5 0.0711(15) 0.0454(14) 0.0432(13) 0.0073(11) -0.0125(12) -0.0037(11) O6 0.0469(12) 0.0429(12) 0.0327(11) 0.0026(9) -0.0060(9) -0.0043(10) O7 0.0624(16) 0.0769(18) 0.0632(17) -0.0095(14) 0.0203(14) -0.0011(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.899(4) . ? C1 C6 1.358(5) . ? C1 C2 1.377(5) . ? C2 C3 1.381(5) . ? C2 H2 0.9300 . ? C3 C4 1.390(5) . ? C3 H3 0.9300 . ? C4 C5 1.394(4) . ? C4 C7 1.512(5) . ? C5 C6 1.381(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.547(4) . ? C7 C10 1.559(4) . ? C7 H7 0.9800 . ? C8 N1 1.436(4) . ? C8 C11 1.517(5) . ? C8 H8 0.9800 . ? C9 N1 1.457(4) . ? C9 C23 1.511(5) . ? C9 C10 1.578(4) . ? C9 H9 0.9800 . ? C10 C13 1.524(4) . ? C10 C18 1.526(4) . ? C11 O1 1.206(5) . ? C11 O2 1.305(5) . ? C12 O2 1.451(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O3 1.194(4) . ? C13 O4 1.333(4) . ? C14 O4 1.484(4) . ? C14 C16 1.499(6) . ? C14 C15 1.504(6) . ? C14 C17 1.519(6) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 O5 1.203(4) . ? C18 O6 1.324(4) . ? C19 O6 1.487(4) . ? C19 C21 1.509(5) . ? C19 C20 1.509(5) . ? C19 C22 1.511(5) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C28 1.373(5) . ? C23 C24 1.388(5) . ? C24 C25 1.371(5) . ? C24 H24 0.9300 . ? C25 C26 1.378(5) . ? C25 H25 0.9300 . ? C26 C27 1.366(5) . ? C26 O7 1.378(4) . ? C27 C28 1.383(5) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 O7 1.373(5) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? N1 H1 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.5(3) . . ? C6 C1 Br1 119.0(3) . . ? C2 C1 Br1 120.4(3) . . ? C1 C2 C3 119.1(3) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 122.0(3) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C3 C4 C5 116.9(3) . . ? C3 C4 C7 124.2(3) . . ? C5 C4 C7 118.8(3) . . ? C6 C5 C4 121.3(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C1 C6 C5 120.2(3) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C4 C7 C8 111.5(2) . . ? C4 C7 C10 115.6(3) . . ? C8 C7 C10 103.6(2) . . ? C4 C7 H7 108.6 . . ? C8 C7 H7 108.6 . . ? C10 C7 H7 108.6 . . ? N1 C8 C11 111.2(3) . . ? N1 C8 C7 107.3(3) . . ? C11 C8 C7 114.6(3) . . ? N1 C8 H8 107.8 . . ? C11 C8 H8 107.8 . . ? C7 C8 H8 107.8 . . ? N1 C9 C23 112.8(3) . . ? N1 C9 C10 105.3(2) . . ? C23 C9 C10 118.3(3) . . ? N1 C9 H9 106.6 . . ? C23 C9 H9 106.6 . . ? C10 C9 H9 106.6 . . ? C13 C10 C18 109.0(2) . . ? C13 C10 C7 112.5(3) . . ? C18 C10 C7 109.3(2) . . ? C13 C10 C9 111.7(2) . . ? C18 C10 C9 110.7(2) . . ? C7 C10 C9 103.6(2) . . ? O1 C11 O2 124.6(4) . . ? O1 C11 C8 124.1(4) . . ? O2 C11 C8 111.3(4) . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 O4 126.1(3) . . ? O3 C13 C10 125.2(3) . . ? O4 C13 C10 108.7(3) . . ? O4 C14 C16 110.6(3) . . ? O4 C14 C15 109.2(3) . . ? C16 C14 C15 113.3(4) . . ? O4 C14 C17 101.5(3) . . ? C16 C14 C17 111.2(4) . . ? C15 C14 C17 110.4(4) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O5 C18 O6 126.0(3) . . ? O5 C18 C10 123.5(3) . . ? O6 C18 C10 110.5(2) . . ? O6 C19 C21 110.3(3) . . ? O6 C19 C20 109.0(3) . . ? C21 C19 C20 113.1(3) . . ? O6 C19 C22 101.6(3) . . ? C21 C19 C22 110.5(3) . . ? C20 C19 C22 111.8(3) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C28 C23 C24 116.9(3) . . ? C28 C23 C9 120.0(3) . . ? C24 C23 C9 122.9(3) . . ? C25 C24 C23 121.7(3) . . ? C25 C24 H24 119.2 . . ? C23 C24 H24 119.2 . . ? C24 C25 C26 120.1(3) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C27 C26 O7 125.3(3) . . ? C27 C26 C25 119.3(3) . . ? O7 C26 C25 115.4(3) . . ? C26 C27 C28 120.0(3) . . ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 . . ? C23 C28 C27 121.9(3) . . ? C23 C28 H28 119.0 . . ? C27 C28 H28 119.0 . . ? O7 C29 H29A 109.5 . . ? O7 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O7 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C8 N1 C9 112.5(3) . . ? C8 N1 H1 123.8 . . ? C9 N1 H1 123.8 . . ? C11 O2 C12 116.8(5) . . ? C13 O4 C14 121.2(3) . . ? C18 O6 C19 122.3(2) . . ? C29 O7 C26 118.0(3) . . ? 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 0.2(6) . . . . ? Br1 C1 C2 C3 178.1(3) . . . . ? C1 C2 C3 C4 0.2(6) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C2 C3 C4 C7 -177.9(3) . . . . ? C3 C4 C5 C6 -0.4(5) . . . . ? C7 C4 C5 C6 177.6(3) . . . . ? C2 C1 C6 C5 -0.6(6) . . . . ? Br1 C1 C6 C5 -178.6(3) . . . . ? C4 C5 C6 C1 0.7(6) . . . . ? C3 C4 C7 C8 57.4(4) . . . . ? C5 C4 C7 C8 -120.5(3) . . . . ? C3 C4 C7 C10 -60.5(4) . . . . ? C5 C4 C7 C10 121.6(3) . . . . ? C4 C7 C8 N1 -102.1(3) . . . . ? C10 C7 C8 N1 22.9(3) . . . . ? C4 C7 C8 C11 133.9(3) . . . . ? C10 C7 C8 C11 -101.2(3) . . . . ? C4 C7 C10 C13 -26.1(3) . . . . ? C8 C7 C10 C13 -148.4(2) . . . . ? C4 C7 C10 C18 -147.3(2) . . . . ? C8 C7 C10 C18 90.4(3) . . . . ? C4 C7 C10 C9 94.6(3) . . . . ? C8 C7 C10 C9 -27.6(3) . . . . ? N1 C9 C10 C13 144.6(3) . . . . ? C23 C9 C10 C13 -88.3(3) . . . . ? N1 C9 C10 C18 -93.7(3) . . . . ? C23 C9 C10 C18 33.4(4) . . . . ? N1 C9 C10 C7 23.3(3) . . . . ? C23 C9 C10 C7 150.4(3) . . . . ? N1 C8 C11 O1 7.0(5) . . . . ? C7 C8 C11 O1 128.9(4) . . . . ? N1 C8 C11 O2 -175.3(3) . . . . ? C7 C8 C11 O2 -53.3(4) . . . . ? C18 C10 C13 O3 -117.5(4) . . . . ? C7 C10 C13 O3 121.1(4) . . . . ? C9 C10 C13 O3 5.2(5) . . . . ? C18 C10 C13 O4 63.1(3) . . . . ? C7 C10 C13 O4 -58.2(3) . . . . ? C9 C10 C13 O4 -174.2(2) . . . . ? C13 C10 C18 O5 -148.7(3) . . . . ? C7 C10 C18 O5 -25.4(4) . . . . ? C9 C10 C18 O5 88.1(3) . . . . ? C13 C10 C18 O6 31.7(3) . . . . ? C7 C10 C18 O6 155.0(2) . . . . ? C9 C10 C18 O6 -91.5(3) . . . . ? N1 C9 C23 C28 -137.9(3) . . . . ? C10 C9 C23 C28 98.7(4) . . . . ? N1 C9 C23 C24 38.0(4) . . . . ? C10 C9 C23 C24 -85.4(4) . . . . ? C28 C23 C24 C25 2.2(5) . . . . ? C9 C23 C24 C25 -173.9(3) . . . . ? C23 C24 C25 C26 -0.4(5) . . . . ? C24 C25 C26 C27 -1.3(5) . . . . ? C24 C25 C26 O7 177.5(3) . . . . ? O7 C26 C27 C28 -177.5(3) . . . . ? C25 C26 C27 C28 1.2(5) . . . . ? C24 C23 C28 C27 -2.3(5) . . . . ? C9 C23 C28 C27 173.8(3) . . . . ? C26 C27 C28 C23 0.7(5) . . . . ? C11 C8 N1 C9 117.7(3) . . . . ? C7 C8 N1 C9 -8.4(4) . . . . ? C23 C9 N1 C8 -140.1(3) . . . . ? C10 C9 N1 C8 -9.6(4) . . . . ? O1 C11 O2 C12 -4.2(7) . . . . ? C8 C11 O2 C12 178.0(4) . . . . ? O3 C13 O4 C14 -2.6(5) . . . . ? C10 C13 O4 C14 176.7(3) . . . . ? C16 C14 O4 C13 -58.0(4) . . . . ? C15 C14 O4 C13 67.4(4) . . . . ? C17 C14 O4 C13 -176.1(3) . . . . ? O5 C18 O6 C19 7.1(4) . . . . ? C10 C18 O6 C19 -173.3(2) . . . . ? C21 C19 O6 C18 -63.4(4) . . . . ? C20 C19 O6 C18 61.4(4) . . . . ? C22 C19 O6 C18 179.5(3) . . . . ? C27 C26 O7 C29 7.0(5) . . . . ? C25 C26 O7 C29 -171.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.564 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.077 # Attachment '90907_0m.cif' data_90907_0m _database_code_depnum_ccdc_archive 'CCDC 747638' #TrackingRef '90907_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H37 N O6' _chemical_formula_weight 531.63 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 10.0784(12) _cell_length_b 12.2383(14) _cell_length_c 12.8767(15) _cell_angle_alpha 91.535(2) _cell_angle_beta 95.552(2) _cell_angle_gamma 111.887(2) _cell_volume 1463.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 201 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9740 _exptl_absorpt_correction_T_max 0.9788 _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 ? _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 8536 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5649 _reflns_number_gt 4300 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.5345P] 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 0.0309(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5649 _refine_ls_number_parameters 360 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.92473(17) 0.83150(14) 0.42146(12) 0.0425(4) Uani 1 1 d . . . C2 C 0.99589(19) 0.81612(17) 0.51192(13) 0.0538(4) Uani 1 1 d . . . H2 H 1.0958 0.8428 0.5189 0.065 Uiso 1 1 calc R . . C3 C 0.9218(2) 0.76092(19) 0.59498(15) 0.0654(5) Uani 1 1 d . . . H3 H 0.9728 0.7520 0.6561 0.079 Uiso 1 1 calc R . . C4 C 0.7763(2) 0.72076(19) 0.58630(15) 0.0654(5) Uani 1 1 d . . . H4 H 0.7281 0.6843 0.6416 0.078 Uiso 1 1 calc R . . C5 C 0.69718(19) 0.73358(17) 0.49463(15) 0.0572(5) Uani 1 1 d . . . C6 C 0.5451(2) 0.6907(2) 0.4834(2) 0.0806(7) Uani 1 1 d . . . H6 H 0.4960 0.6531 0.5379 0.097 Uiso 1 1 calc R . . C7 C 0.4696(2) 0.7033(3) 0.3950(2) 0.0960(9) Uani 1 1 d . . . H7 H 0.3696 0.6736 0.3887 0.115 Uiso 1 1 calc R . . C8 C 0.5422(2) 0.7608(3) 0.3136(2) 0.0881(8) Uani 1 1 d . . . H8 H 0.4899 0.7707 0.2535 0.106 Uiso 1 1 calc R . . C9 C 0.6882(2) 0.80258(19) 0.32035(16) 0.0628(5) Uani 1 1 d . . . H9 H 0.7340 0.8396 0.2643 0.075 Uiso 1 1 calc R . . C10 C 0.77145(18) 0.79088(15) 0.41057(13) 0.0475(4) Uani 1 1 d . . . C11 C 1.00860(17) 0.89307(14) 0.33370(12) 0.0416(4) Uani 1 1 d . . . H11 H 0.9585 0.9400 0.3000 0.050 Uiso 1 1 calc R . . C12 C 1.03359(16) 0.81199(13) 0.24541(12) 0.0377(3) Uani 1 1 d . . . C13 C 1.19684(16) 0.87714(13) 0.23242(12) 0.0405(4) Uani 1 1 d . . . H13 H 1.2493 0.8411 0.2789 0.049 Uiso 1 1 calc R . . C14 C 1.23122(18) 1.00111(14) 0.28150(13) 0.0456(4) Uani 1 1 d . . . H14 H 1.1878 1.0437 0.2348 0.055 Uiso 1 1 calc R . . C15 C 1.39037(19) 1.07234(16) 0.30682(14) 0.0519(4) Uani 1 1 d . . . C16 C 1.6097(2) 1.0796(2) 0.3955(2) 0.0942(8) Uani 1 1 d . . . H16A H 1.6576 1.0902 0.3335 0.141 Uiso 1 1 calc R . . H16B H 1.6446 1.0335 0.4416 0.141 Uiso 1 1 calc R . . H16C H 1.6286 1.1553 0.4300 0.141 Uiso 1 1 calc R . . C17 C 1.24363(17) 0.86981(14) 0.12493(13) 0.0442(4) Uani 1 1 d . . . C18 C 1.2583(2) 0.95623(17) 0.05512(15) 0.0624(5) Uani 1 1 d . . . H18 H 1.2343 1.0203 0.0723 0.075 Uiso 1 1 calc R . . C19 C 1.3084(3) 0.9485(2) -0.04046(17) 0.0777(7) Uani 1 1 d . . . H19 H 1.3175 1.0073 -0.0867 0.093 Uiso 1 1 calc R . . C20 C 1.3445(2) 0.8558(2) -0.06688(18) 0.0766(7) Uani 1 1 d . . . H20 H 1.3793 0.8515 -0.1305 0.092 Uiso 1 1 calc R . . C21 C 1.3291(2) 0.7684(2) 0.00089(18) 0.0735(6) Uani 1 1 d . . . H21 H 1.3532 0.7046 -0.0171 0.088 Uiso 1 1 calc R . . C22 C 1.27789(19) 0.77458(17) 0.09595(15) 0.0565(5) Uani 1 1 d . . . H22 H 1.2664 0.7142 0.1408 0.068 Uiso 1 1 calc R . . C23 C 0.94306(17) 0.81084(14) 0.14234(12) 0.0407(4) Uani 1 1 d . . . C24 C 0.8331(2) 0.69385(17) -0.02313(13) 0.0580(5) Uani 1 1 d . . . C25 C 0.9143(3) 0.7844(2) -0.09513(15) 0.0785(7) Uani 1 1 d . . . H25A H 0.9286 0.8619 -0.0671 0.118 Uiso 1 1 calc R . . H25B H 0.8598 0.7696 -0.1630 0.118 Uiso 1 1 calc R . . H25C H 1.0059 0.7791 -0.1011 0.118 Uiso 1 1 calc R . . C26 C 0.8249(4) 0.5719(2) -0.05742(18) 0.1010(9) Uani 1 1 d . . . H26A H 0.9204 0.5721 -0.0558 0.151 Uiso 1 1 calc R . . H26B H 0.7766 0.5504 -0.1273 0.151 Uiso 1 1 calc R . . H26C H 0.7723 0.5159 -0.0109 0.151 Uiso 1 1 calc R . . C27 C 0.6851(2) 0.6953(2) -0.01165(18) 0.0860(7) Uani 1 1 d . . . H27A H 0.6405 0.6406 0.0385 0.129 Uiso 1 1 calc R . . H27B H 0.6266 0.6729 -0.0780 0.129 Uiso 1 1 calc R . . H27C H 0.6946 0.7733 0.0118 0.129 Uiso 1 1 calc R . . C28 C 1.00422(17) 0.68725(14) 0.28027(12) 0.0418(4) Uani 1 1 d . . . C29 C 0.8033(2) 0.49948(14) 0.29514(14) 0.0538(5) Uani 1 1 d . . . C30 C 0.8679(3) 0.42966(19) 0.2318(2) 0.0871(7) Uani 1 1 d . . . H30A H 0.8631 0.4490 0.1601 0.131 Uiso 1 1 calc R . . H30B H 0.8150 0.3468 0.2359 0.131 Uiso 1 1 calc R . . H30C H 0.9666 0.4491 0.2592 0.131 Uiso 1 1 calc R . . C31 C 0.6456(2) 0.46650(19) 0.2592(2) 0.0844(7) Uani 1 1 d . . . H31A H 0.6096 0.5161 0.2971 0.127 Uiso 1 1 calc R . . H31B H 0.5936 0.3855 0.2719 0.127 Uiso 1 1 calc R . . H31C H 0.6331 0.4769 0.1858 0.127 Uiso 1 1 calc R . . C32 C 0.8291(3) 0.49006(19) 0.41118(16) 0.0764(6) Uani 1 1 d . . . H32A H 0.9308 0.5179 0.4326 0.115 Uiso 1 1 calc R . . H32B H 0.7848 0.4091 0.4272 0.115 Uiso 1 1 calc R . . H32C H 0.7883 0.5371 0.4477 0.115 Uiso 1 1 calc R . . N1 N 1.15500(15) 0.97311(12) 0.37364(11) 0.0506(4) Uani 1 1 d . . . H1 H 1.1885 0.9980 0.4375 0.061 Uiso 1 1 calc R . . O1 O 1.44990(16) 1.16608(12) 0.27349(12) 0.0777(5) Uani 1 1 d . . . O2 O 1.45627(14) 1.01926(14) 0.36740(13) 0.0825(5) Uani 1 1 d . . . O3 O 0.90836(14) 0.89179(11) 0.11901(9) 0.0575(3) Uani 1 1 d . . . O4 O 0.91839(12) 0.71491(10) 0.08127(8) 0.0478(3) Uani 1 1 d . . . O5 O 1.09662(14) 0.65386(11) 0.31390(12) 0.0659(4) Uani 1 1 d . . . O6 O 0.86380(11) 0.62523(9) 0.27179(9) 0.0445(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0381(9) 0.0465(9) 0.0394(8) -0.0017(7) 0.0068(7) 0.0116(7) C2 0.0419(10) 0.0686(12) 0.0442(10) 0.0028(8) 0.0043(8) 0.0134(9) C3 0.0663(13) 0.0853(14) 0.0410(10) 0.0093(9) 0.0061(9) 0.0240(11) C4 0.0630(13) 0.0772(14) 0.0485(11) 0.0085(9) 0.0220(9) 0.0140(11) C5 0.0457(10) 0.0643(12) 0.0543(11) -0.0023(9) 0.0154(8) 0.0104(9) C6 0.0476(12) 0.1009(18) 0.0813(16) -0.0001(13) 0.0253(11) 0.0102(12) C7 0.0385(12) 0.138(2) 0.099(2) -0.0043(17) 0.0107(13) 0.0193(14) C8 0.0485(13) 0.132(2) 0.0810(16) 0.0023(15) -0.0046(11) 0.0339(14) C9 0.0453(11) 0.0849(14) 0.0583(11) 0.0039(10) 0.0042(9) 0.0252(10) C10 0.0404(9) 0.0523(10) 0.0469(9) -0.0037(7) 0.0077(7) 0.0140(8) C11 0.0380(8) 0.0411(8) 0.0415(8) 0.0005(7) 0.0059(7) 0.0101(7) C12 0.0331(8) 0.0366(8) 0.0393(8) 0.0037(6) 0.0047(6) 0.0082(6) C13 0.0340(8) 0.0388(8) 0.0440(9) 0.0036(7) 0.0057(7) 0.0078(7) C14 0.0421(9) 0.0405(9) 0.0472(9) 0.0020(7) 0.0096(7) 0.0066(7) C15 0.0485(10) 0.0465(10) 0.0483(10) -0.0033(8) 0.0130(8) 0.0025(8) C16 0.0412(12) 0.1054(19) 0.1056(19) 0.0088(15) -0.0036(12) -0.0042(12) C17 0.0331(8) 0.0455(9) 0.0474(9) -0.0017(7) 0.0069(7) 0.0071(7) C18 0.0730(13) 0.0553(11) 0.0596(12) 0.0104(9) 0.0286(10) 0.0196(10) C19 0.0860(16) 0.0757(15) 0.0604(13) 0.0116(11) 0.0335(12) 0.0115(12) C20 0.0627(14) 0.0916(17) 0.0607(13) -0.0123(12) 0.0270(11) 0.0085(12) C21 0.0651(13) 0.0821(15) 0.0735(14) -0.0237(12) 0.0097(11) 0.0294(12) C22 0.0513(11) 0.0585(11) 0.0584(11) -0.0056(9) 0.0042(9) 0.0203(9) C23 0.0377(8) 0.0402(8) 0.0411(8) 0.0057(7) 0.0079(7) 0.0101(7) C24 0.0641(12) 0.0627(12) 0.0374(9) -0.0015(8) -0.0050(8) 0.0157(9) C25 0.0932(17) 0.0948(17) 0.0424(11) 0.0131(10) 0.0087(11) 0.0287(14) C26 0.158(3) 0.0766(16) 0.0572(14) -0.0196(12) -0.0182(15) 0.0405(17) C27 0.0561(13) 0.1107(19) 0.0709(15) 0.0000(13) -0.0134(11) 0.0137(13) C28 0.0395(9) 0.0406(8) 0.0409(9) 0.0049(7) 0.0041(7) 0.0102(7) C29 0.0575(11) 0.0348(9) 0.0566(11) 0.0100(7) 0.0056(9) 0.0031(8) C30 0.112(2) 0.0462(12) 0.0975(18) 0.0003(11) 0.0229(15) 0.0215(12) C31 0.0592(13) 0.0589(13) 0.1022(18) 0.0198(12) -0.0061(12) -0.0126(10) C32 0.0830(16) 0.0646(13) 0.0644(13) 0.0248(10) 0.0061(11) 0.0075(11) N1 0.0427(8) 0.0514(8) 0.0420(8) -0.0070(6) 0.0079(6) -0.0002(6) O1 0.0657(9) 0.0538(8) 0.0898(11) 0.0139(7) 0.0201(8) -0.0082(7) O2 0.0410(8) 0.0769(10) 0.1036(12) 0.0230(9) -0.0072(8) -0.0049(7) O3 0.0718(9) 0.0548(7) 0.0509(7) 0.0067(6) -0.0004(6) 0.0310(7) O4 0.0552(7) 0.0476(7) 0.0379(6) 0.0001(5) -0.0005(5) 0.0180(6) O5 0.0471(7) 0.0574(8) 0.0928(10) 0.0274(7) 0.0026(7) 0.0189(6) O6 0.0393(6) 0.0359(6) 0.0501(7) 0.0079(5) 0.0045(5) 0.0046(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.363(2) . ? C1 C10 1.427(2) . ? C1 C11 1.521(2) . ? C2 C3 1.405(3) . ? C3 C4 1.354(3) . ? C4 C5 1.405(3) . ? C5 C6 1.414(3) . ? C5 C10 1.425(2) . ? C6 C7 1.351(3) . ? C7 C8 1.391(4) . ? C8 C9 1.359(3) . ? C9 C10 1.409(3) . ? C11 N1 1.466(2) . ? C11 C12 1.588(2) . ? C12 C28 1.531(2) . ? C12 C23 1.533(2) . ? C12 C13 1.566(2) . ? C13 C17 1.516(2) . ? C13 C14 1.528(2) . ? C14 N1 1.455(2) . ? C14 C15 1.510(2) . ? C15 O1 1.193(2) . ? C15 O2 1.312(2) . ? C16 O2 1.447(2) . ? C17 C18 1.381(2) . ? C17 C22 1.385(2) . ? C18 C19 1.389(3) . ? C19 C20 1.359(3) . ? C20 C21 1.372(3) . ? C21 C22 1.384(3) . ? C23 O3 1.2034(19) . ? C23 O4 1.3243(19) . ? C24 O4 1.485(2) . ? C24 C25 1.511(3) . ? C24 C26 1.515(3) . ? C24 C27 1.520(3) . ? C28 O5 1.1987(19) . ? C28 O6 1.3250(19) . ? C29 O6 1.4804(19) . ? C29 C31 1.508(3) . ? C29 C32 1.507(3) . ? C29 C30 1.517(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C10 119.40(15) . . ? C2 C1 C11 120.10(15) . . ? C10 C1 C11 120.49(14) . . ? C1 C2 C3 121.53(17) . . ? C4 C3 C2 120.22(18) . . ? C3 C4 C5 120.74(17) . . ? C4 C5 C6 121.63(19) . . ? C4 C5 C10 119.45(17) . . ? C6 C5 C10 118.92(19) . . ? C7 C6 C5 121.4(2) . . ? C6 C7 C8 119.7(2) . . ? C9 C8 C7 121.1(2) . . ? C8 C9 C10 121.2(2) . . ? C9 C10 C1 123.69(16) . . ? C9 C10 C5 117.66(16) . . ? C1 C10 C5 118.64(16) . . ? N1 C11 C1 111.56(13) . . ? N1 C11 C12 103.36(12) . . ? C1 C11 C12 117.22(13) . . ? C28 C12 C23 111.95(12) . . ? C28 C12 C13 110.70(12) . . ? C23 C12 C13 109.11(12) . . ? C28 C12 C11 111.36(12) . . ? C23 C12 C11 110.52(12) . . ? C13 C12 C11 102.82(11) . . ? C17 C13 C14 116.32(13) . . ? C17 C13 C12 117.82(13) . . ? C14 C13 C12 103.01(12) . . ? N1 C14 C15 113.44(14) . . ? N1 C14 C13 100.55(12) . . ? C15 C14 C13 113.70(14) . . ? O1 C15 O2 123.75(18) . . ? O1 C15 C14 123.31(19) . . ? O2 C15 C14 112.92(15) . . ? C18 C17 C22 118.06(17) . . ? C18 C17 C13 122.85(16) . . ? C22 C17 C13 119.05(16) . . ? C17 C18 C19 120.8(2) . . ? C20 C19 C18 120.5(2) . . ? C19 C20 C21 119.6(2) . . ? C20 C21 C22 120.4(2) . . ? C21 C22 C17 120.7(2) . . ? O3 C23 O4 125.42(15) . . ? O3 C23 C12 122.93(14) . . ? O4 C23 C12 111.48(13) . . ? O4 C24 C25 109.64(15) . . ? O4 C24 C26 101.78(15) . . ? C25 C24 C26 110.96(19) . . ? O4 C24 C27 109.72(16) . . ? C25 C24 C27 112.45(19) . . ? C26 C24 C27 111.8(2) . . ? O5 C28 O6 125.86(15) . . ? O5 C28 C12 123.83(15) . . ? O6 C28 C12 110.26(13) . . ? O6 C29 C31 101.66(14) . . ? O6 C29 C32 109.22(15) . . ? C31 C29 C32 111.49(18) . . ? O6 C29 C30 109.73(15) . . ? C31 C29 C30 111.48(19) . . ? C32 C29 C30 112.69(19) . . ? C14 N1 C11 104.87(12) . . ? C15 O2 C16 117.33(17) . . ? C23 O4 C24 121.51(13) . . ? C28 O6 C29 122.38(13) . . ? 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 C10 C1 C2 C3 0.1(3) . . . . ? C11 C1 C2 C3 179.21(17) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 179.1(2) . . . . ? C3 C4 C5 C10 -0.8(3) . . . . ? C4 C5 C6 C7 -180.0(2) . . . . ? C10 C5 C6 C7 -0.1(4) . . . . ? C5 C6 C7 C8 -0.8(4) . . . . ? C6 C7 C8 C9 1.4(4) . . . . ? C7 C8 C9 C10 -1.0(4) . . . . ? C8 C9 C10 C1 179.1(2) . . . . ? C8 C9 C10 C5 0.0(3) . . . . ? C2 C1 C10 C9 -179.98(18) . . . . ? C11 C1 C10 C9 0.9(3) . . . . ? C2 C1 C10 C5 -0.9(3) . . . . ? C11 C1 C10 C5 179.94(15) . . . . ? C4 C5 C10 C9 -179.61(18) . . . . ? C6 C5 C10 C9 0.5(3) . . . . ? C4 C5 C10 C1 1.3(3) . . . . ? C6 C5 C10 C1 -178.57(18) . . . . ? C2 C1 C11 N1 -25.4(2) . . . . ? C10 C1 C11 N1 153.76(15) . . . . ? C2 C1 C11 C12 93.50(19) . . . . ? C10 C1 C11 C12 -87.38(19) . . . . ? N1 C11 C12 C28 107.29(14) . . . . ? C1 C11 C12 C28 -15.86(19) . . . . ? N1 C11 C12 C23 -127.61(13) . . . . ? C1 C11 C12 C23 109.23(15) . . . . ? N1 C11 C12 C13 -11.28(15) . . . . ? C1 C11 C12 C13 -134.43(14) . . . . ? C28 C12 C13 C17 92.93(16) . . . . ? C23 C12 C13 C17 -30.69(18) . . . . ? C11 C12 C13 C17 -148.03(14) . . . . ? C28 C12 C13 C14 -137.53(13) . . . . ? C23 C12 C13 C14 98.84(14) . . . . ? C11 C12 C13 C14 -18.50(15) . . . . ? C17 C13 C14 N1 172.56(13) . . . . ? C12 C13 C14 N1 42.12(15) . . . . ? C17 C13 C14 C15 -65.86(19) . . . . ? C12 C13 C14 C15 163.70(14) . . . . ? N1 C14 C15 O1 -122.75(19) . . . . ? C13 C14 C15 O1 123.14(19) . . . . ? N1 C14 C15 O2 58.5(2) . . . . ? C13 C14 C15 O2 -55.6(2) . . . . ? C14 C13 C17 C18 -27.1(2) . . . . ? C12 C13 C17 C18 95.93(19) . . . . ? C14 C13 C17 C22 150.74(15) . . . . ? C12 C13 C17 C22 -86.23(19) . . . . ? C22 C17 C18 C19 -1.1(3) . . . . ? C13 C17 C18 C19 176.73(18) . . . . ? C17 C18 C19 C20 -0.2(3) . . . . ? C18 C19 C20 C21 0.9(4) . . . . ? C19 C20 C21 C22 -0.3(3) . . . . ? C20 C21 C22 C17 -1.1(3) . . . . ? C18 C17 C22 C21 1.8(3) . . . . ? C13 C17 C22 C21 -176.19(17) . . . . ? C28 C12 C23 O3 152.86(15) . . . . ? C13 C12 C23 O3 -84.26(18) . . . . ? C11 C12 C23 O3 28.1(2) . . . . ? C28 C12 C23 O4 -31.68(18) . . . . ? C13 C12 C23 O4 91.21(15) . . . . ? C11 C12 C23 O4 -156.43(12) . . . . ? C23 C12 C28 O5 136.51(17) . . . . ? C13 C12 C28 O5 14.5(2) . . . . ? C11 C12 C28 O5 -99.20(19) . . . . ? C23 C12 C28 O6 -46.08(17) . . . . ? C13 C12 C28 O6 -168.06(12) . . . . ? C11 C12 C28 O6 78.21(15) . . . . ? C15 C14 N1 C11 -173.39(14) . . . . ? C13 C14 N1 C11 -51.62(16) . . . . ? C1 C11 N1 C14 166.03(13) . . . . ? C12 C11 N1 C14 39.21(16) . . . . ? O1 C15 O2 C16 0.7(3) . . . . ? C14 C15 O2 C16 179.37(18) . . . . ? O3 C23 O4 C24 -4.6(2) . . . . ? C12 C23 O4 C24 -179.88(13) . . . . ? C25 C24 O4 C23 66.9(2) . . . . ? C26 C24 O4 C23 -175.60(18) . . . . ? C27 C24 O4 C23 -57.1(2) . . . . ? O5 C28 O6 C29 -5.7(3) . . . . ? C12 C28 O6 C29 176.99(13) . . . . ? C31 C29 O6 C28 -172.16(16) . . . . ? C32 C29 O6 C28 69.9(2) . . . . ? C30 C29 O6 C28 -54.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.452 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.030 # Attachment '91218xzy_0m.cif' data_91218xzy_0m _database_code_depnum_ccdc_archive 'CCDC 761891' #TrackingRef '91218xzy_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_absolute_configuration 7S,8S,9S _chemical_formula_sum 'C29 H36 Br N O6' _chemical_formula_weight 574.50 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.202(2) _cell_length_b 11.863(2) _cell_length_c 22.167(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2945.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.435 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6566 _exptl_absorpt_correction_T_max 0.7430 _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 ? _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 17768 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 26.50 _reflns_number_total 6077 _reflns_number_gt 4688 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0658P)^2^+1.6081P] 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 0.0072(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.008(12) _refine_ls_number_reflns 6077 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1460 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.025 _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 Br1 Br 0.77495(6) 1.00987(6) 1.00554(3) 0.1091(3) Uani 1 1 d . . . C1 C 0.6523(4) 0.9369(4) 0.96050(17) 0.0601(10) Uani 1 1 d . . . C2 C 0.5906(4) 0.8501(4) 0.98654(18) 0.0660(11) Uani 1 1 d . . . H2 H 0.6070 0.8281 1.0259 0.079 Uiso 1 1 calc R . . C3 C 0.5033(4) 0.7957(4) 0.95330(16) 0.0543(9) Uani 1 1 d . . . H3 H 0.4596 0.7378 0.9710 0.065 Uiso 1 1 calc R . . C4 C 0.4799(3) 0.8260(3) 0.89430(14) 0.0396(7) Uani 1 1 d . . . C5 C 0.5445(3) 0.9133(3) 0.86922(16) 0.0472(8) Uani 1 1 d . . . H5 H 0.5300 0.9345 0.8295 0.057 Uiso 1 1 calc R . . C6 C 0.6307(3) 0.9701(3) 0.90239(17) 0.0541(9) Uani 1 1 d . . . H6 H 0.6730 1.0296 0.8854 0.065 Uiso 1 1 calc R . . C7 C 0.3882(3) 0.7585(3) 0.85864(15) 0.0386(7) Uani 1 1 d . . . H7 H 0.3476 0.7063 0.8861 0.046 Uiso 1 1 calc R . . C8 C 0.4462(3) 0.6897(3) 0.80646(16) 0.0436(8) Uani 1 1 d . . . C9 C 0.3391(3) 0.8448(3) 0.75930(15) 0.0444(8) Uani 1 1 d . . . H9 H 0.3781 0.9186 0.7568 0.053 Uiso 1 1 calc R . . C10 C 0.2924(3) 0.8324(3) 0.82615(14) 0.0379(7) Uani 1 1 d . . . C11 C 0.2448(3) 0.8425(3) 0.70974(15) 0.0447(8) Uani 1 1 d . . . C12 C 0.2204(4) 0.7480(4) 0.67516(18) 0.0607(10) Uani 1 1 d . . . H12 H 0.2614 0.6812 0.6826 0.073 Uiso 1 1 calc R . . C13 C 0.1361(5) 0.7516(4) 0.6297(2) 0.0705(13) Uani 1 1 d . . . H13 H 0.1218 0.6876 0.6065 0.085 Uiso 1 1 calc R . . C14 C 0.0738(5) 0.8479(4) 0.6185(2) 0.0708(13) Uani 1 1 d . . . H14 H 0.0176 0.8498 0.5876 0.085 Uiso 1 1 calc R . . C15 C 0.0941(4) 0.9414(4) 0.6526(2) 0.0680(12) Uani 1 1 d . . . H15 H 0.0499 1.0065 0.6459 0.082 Uiso 1 1 calc R . . C16 C 0.1810(4) 0.9397(3) 0.69750(18) 0.0578(10) Uani 1 1 d . . . H16 H 0.1963 1.0048 0.7196 0.069 Uiso 1 1 calc R . . C17 C 0.1699(3) 0.7737(3) 0.82781(15) 0.0414(7) Uani 1 1 d . . . C18 C -0.0444(3) 0.8185(3) 0.81729(17) 0.0491(9) Uani 1 1 d . . . C19 C -0.0669(4) 0.7358(4) 0.7662(2) 0.0595(10) Uani 1 1 d . . . H19A H -0.0338 0.7652 0.7295 0.089 Uiso 1 1 calc R . . H19B H -0.1513 0.7251 0.7613 0.089 Uiso 1 1 calc R . . H19C H -0.0299 0.6650 0.7756 0.089 Uiso 1 1 calc R . . C20 C -0.1022(4) 0.9313(4) 0.8043(2) 0.0729(13) Uani 1 1 d . . . H20A H -0.0883 0.9815 0.8376 0.109 Uiso 1 1 calc R . . H20B H -0.1865 0.9211 0.7989 0.109 Uiso 1 1 calc R . . H20C H -0.0684 0.9628 0.7683 0.109 Uiso 1 1 calc R . . C21 C -0.0826(4) 0.7739(4) 0.87815(19) 0.0626(11) Uani 1 1 d . . . H21A H -0.0456 0.7021 0.8852 0.094 Uiso 1 1 calc R . . H21B H -0.1678 0.7655 0.8789 0.094 Uiso 1 1 calc R . . H21C H -0.0586 0.8259 0.9091 0.094 Uiso 1 1 calc R . . C22 C 0.2760(3) 0.9479(3) 0.85545(15) 0.0420(7) Uani 1 1 d . . . C23 C 0.2271(4) 1.0323(3) 0.95401(18) 0.0569(10) Uani 1 1 d . . . C24 C 0.1210(6) 1.0987(5) 0.9320(3) 0.0966(19) Uani 1 1 d . . . H24A H 0.1375 1.1281 0.8925 0.145 Uiso 1 1 calc R . . H24B H 0.1056 1.1599 0.9592 0.145 Uiso 1 1 calc R . . H24C H 0.0523 1.0504 0.9302 0.145 Uiso 1 1 calc R . . C25 C 0.2016(6) 0.9765(5) 1.0138(2) 0.0898(17) Uani 1 1 d . . . H25A H 0.1371 0.9239 1.0091 0.135 Uiso 1 1 calc R . . H25B H 0.1797 1.0328 1.0429 0.135 Uiso 1 1 calc R . . H25C H 0.2716 0.9374 1.0274 0.135 Uiso 1 1 calc R . . C26 C 0.3385(5) 1.1016(4) 0.9573(2) 0.0759(13) Uani 1 1 d . . . H26A H 0.4035 1.0553 0.9708 0.114 Uiso 1 1 calc R . . H26B H 0.3269 1.1626 0.9852 0.114 Uiso 1 1 calc R . . H26C H 0.3565 1.1313 0.9181 0.114 Uiso 1 1 calc R . . C27 C 0.5795(4) 0.6617(4) 0.8154(2) 0.0672(12) Uani 1 1 d . . . H27A H 0.6073 0.6175 0.7819 0.101 Uiso 1 1 calc R . . H27B H 0.5895 0.6197 0.8520 0.101 Uiso 1 1 calc R . . H27C H 0.6246 0.7303 0.8177 0.101 Uiso 1 1 calc R . . C28 C 0.3850(3) 0.5756(3) 0.79722(18) 0.0526(9) Uani 1 1 d . . . C29 C 0.3298(7) 0.4047(4) 0.8413(3) 0.098(2) Uani 1 1 d . . . H29A H 0.2449 0.4110 0.8366 0.147 Uiso 1 1 calc R . . H29B H 0.3473 0.3616 0.8769 0.147 Uiso 1 1 calc R . . H29C H 0.3632 0.3677 0.8067 0.147 Uiso 1 1 calc R . . N1 N 0.4332(3) 0.7607(3) 0.75380(14) 0.0556(9) Uani 1 1 d . . . H1 H 0.4771 0.7539 0.7222 0.067 Uiso 1 1 calc R . . O1 O 0.1574(2) 0.6735(2) 0.83436(14) 0.0564(7) Uani 1 1 d . . . O2 O 0.0842(2) 0.84838(19) 0.81944(12) 0.0450(6) Uani 1 1 d . . . O3 O 0.2885(3) 1.0363(2) 0.83056(12) 0.0588(7) Uani 1 1 d . . . O4 O 0.2456(2) 0.93429(19) 0.91306(10) 0.0469(6) Uani 1 1 d . . . O5 O 0.3811(3) 0.5158(2) 0.84705(13) 0.0694(8) Uani 1 1 d . . . O6 O 0.3548(3) 0.5407(3) 0.74886(13) 0.0668(8) 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 Br1 0.0962(4) 0.1529(6) 0.0781(4) -0.0132(4) -0.0327(3) -0.0519(4) C1 0.048(2) 0.085(3) 0.047(2) -0.012(2) -0.0137(17) -0.013(2) C2 0.065(3) 0.096(3) 0.0376(19) 0.006(2) -0.0121(18) -0.009(2) C3 0.053(2) 0.068(2) 0.0428(19) 0.0106(17) -0.0002(17) -0.0070(19) C4 0.0314(16) 0.0498(19) 0.0376(16) -0.0019(14) -0.0003(13) 0.0015(14) C5 0.044(2) 0.061(2) 0.0373(17) 0.0023(15) -0.0020(14) -0.0030(16) C6 0.048(2) 0.064(2) 0.050(2) -0.0007(18) 0.0002(16) -0.0150(18) C7 0.0341(16) 0.0416(18) 0.0402(17) 0.0001(14) -0.0002(13) 0.0015(13) C8 0.0324(17) 0.051(2) 0.0470(19) -0.0062(16) 0.0021(14) 0.0042(15) C9 0.0400(19) 0.051(2) 0.0420(17) 0.0018(15) 0.0039(14) -0.0041(16) C10 0.0338(17) 0.0430(17) 0.0369(16) 0.0005(13) -0.0016(13) -0.0003(13) C11 0.047(2) 0.049(2) 0.0378(16) 0.0068(14) 0.0049(15) -0.0041(16) C12 0.070(3) 0.058(2) 0.054(2) -0.0056(18) -0.012(2) 0.001(2) C13 0.086(3) 0.070(3) 0.056(2) -0.013(2) -0.012(2) -0.007(3) C14 0.075(3) 0.091(3) 0.046(2) 0.011(2) -0.016(2) -0.016(3) C15 0.077(3) 0.059(2) 0.068(3) 0.018(2) -0.016(2) -0.004(2) C16 0.066(3) 0.051(2) 0.056(2) 0.0058(18) -0.0103(19) -0.0072(19) C17 0.0359(17) 0.047(2) 0.0410(17) -0.0011(15) -0.0003(13) 0.0000(14) C18 0.0318(17) 0.060(2) 0.055(2) 0.0051(17) -0.0027(15) -0.0017(16) C19 0.045(2) 0.074(3) 0.060(2) 0.001(2) -0.0085(18) -0.012(2) C20 0.051(2) 0.078(3) 0.090(3) 0.010(3) -0.008(2) 0.020(2) C21 0.045(2) 0.082(3) 0.061(3) 0.007(2) 0.0051(19) 0.000(2) C22 0.0359(17) 0.0432(19) 0.0470(18) -0.0001(15) -0.0060(14) 0.0012(14) C23 0.061(2) 0.051(2) 0.058(2) -0.0139(17) -0.0005(18) 0.0071(19) C24 0.092(4) 0.092(4) 0.106(4) -0.042(3) -0.017(3) 0.041(3) C25 0.119(5) 0.086(3) 0.064(3) -0.023(3) 0.023(3) -0.003(3) C26 0.085(3) 0.073(3) 0.070(3) -0.026(2) -0.002(3) -0.012(3) C27 0.040(2) 0.084(3) 0.077(3) -0.029(2) 0.0001(19) 0.013(2) C28 0.045(2) 0.057(2) 0.055(2) -0.0085(19) 0.0080(17) 0.0066(17) C29 0.156(6) 0.050(3) 0.087(4) -0.008(2) 0.027(4) -0.010(3) N1 0.0475(18) 0.071(2) 0.0486(18) -0.0025(15) 0.0126(14) 0.0009(17) O1 0.0414(14) 0.0432(15) 0.0845(19) 0.0037(13) -0.0022(13) 0.0002(11) O2 0.0331(12) 0.0435(13) 0.0584(15) 0.0002(11) -0.0041(11) 0.0031(10) O3 0.0743(19) 0.0444(15) 0.0576(15) 0.0037(12) -0.0047(13) -0.0031(13) O4 0.0514(14) 0.0424(12) 0.0469(13) -0.0074(10) 0.0018(11) 0.0040(11) O5 0.102(2) 0.0447(15) 0.0614(16) -0.0058(13) 0.0059(15) 0.0046(15) O6 0.074(2) 0.0677(18) 0.0589(17) -0.0201(14) 0.0005(13) -0.0042(16) _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 C1 1.907(4) . ? C1 C2 1.367(6) . ? C1 C6 1.368(6) . ? C2 C3 1.384(6) . ? C2 H2 0.9300 . ? C3 C4 1.381(5) . ? C3 H3 0.9300 . ? C4 C5 1.380(5) . ? C4 C7 1.524(5) . ? C5 C6 1.388(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C10 1.561(5) . ? C7 C8 1.558(5) . ? C7 H7 0.9800 . ? C8 N1 1.447(5) . ? C8 C28 1.532(6) . ? C8 C27 1.542(5) . ? C9 N1 1.456(5) . ? C9 C11 1.524(5) . ? C9 C10 1.578(5) . ? C9 H9 0.9800 . ? C10 C22 1.528(5) . ? C10 C17 1.539(5) . ? C11 C12 1.385(5) . ? C11 C16 1.384(5) . ? C12 C13 1.382(6) . ? C12 H12 0.9300 . ? C13 C14 1.362(7) . ? C13 H13 0.9300 . ? C14 C15 1.362(7) . ? C14 H14 0.9300 . ? C15 C16 1.392(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O1 1.206(4) . ? C17 O2 1.320(4) . ? C18 O2 1.484(4) . ? C18 C21 1.511(6) . ? C18 C20 1.514(6) . ? C18 C19 1.519(6) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O3 1.194(4) . ? C22 O4 1.332(4) . ? C23 O4 1.489(4) . ? C23 C26 1.496(7) . ? C23 C25 1.508(7) . ? C23 C24 1.507(7) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 O6 1.198(5) . ? C28 O5 1.313(5) . ? C29 O5 1.443(6) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? N1 H1 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.6(4) . . ? C2 C1 Br1 119.0(3) . . ? C6 C1 Br1 119.3(3) . . ? C1 C2 C3 118.9(4) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 121.1(4) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 118.5(3) . . ? C3 C4 C7 118.9(3) . . ? C5 C4 C7 122.6(3) . . ? C4 C5 C6 121.0(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 118.8(4) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C4 C7 C10 114.1(3) . . ? C4 C7 C8 112.3(3) . . ? C10 C7 C8 103.8(3) . . ? C4 C7 H7 108.8 . . ? C10 C7 H7 108.8 . . ? C8 C7 H7 108.8 . . ? N1 C8 C28 111.2(3) . . ? N1 C8 C27 109.0(3) . . ? C28 C8 C27 105.1(3) . . ? N1 C8 C7 104.6(3) . . ? C28 C8 C7 112.1(3) . . ? C27 C8 C7 115.0(3) . . ? N1 C9 C11 115.4(3) . . ? N1 C9 C10 104.8(3) . . ? C11 C9 C10 116.4(3) . . ? N1 C9 H9 106.5 . . ? C11 C9 H9 106.5 . . ? C10 C9 H9 106.5 . . ? C22 C10 C17 106.7(3) . . ? C22 C10 C7 113.0(3) . . ? C17 C10 C7 110.4(3) . . ? C22 C10 C9 110.8(3) . . ? C17 C10 C9 111.1(3) . . ? C7 C10 C9 104.9(3) . . ? C12 C11 C16 117.6(4) . . ? C12 C11 C9 123.4(3) . . ? C16 C11 C9 119.0(3) . . ? C13 C12 C11 120.9(4) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 C12 120.6(4) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 119.8(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.1(4) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C11 C16 C15 120.9(4) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? O1 C17 O2 126.4(3) . . ? O1 C17 C10 123.5(3) . . ? O2 C17 C10 110.0(3) . . ? O2 C18 C21 109.3(3) . . ? O2 C18 C20 102.1(3) . . ? C21 C18 C20 111.0(4) . . ? O2 C18 C19 109.8(3) . . ? C21 C18 C19 113.1(3) . . ? C20 C18 C19 111.0(4) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O3 C22 O4 125.5(3) . . ? O3 C22 C10 125.3(3) . . ? O4 C22 C10 109.3(3) . . ? O4 C23 C26 110.1(3) . . ? O4 C23 C25 102.7(3) . . ? C26 C23 C25 110.9(4) . . ? O4 C23 C24 108.7(3) . . ? C26 C23 C24 112.7(4) . . ? C25 C23 C24 111.4(5) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C8 C27 H27A 109.5 . . ? C8 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C8 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O6 C28 O5 123.8(4) . . ? O6 C28 C8 123.5(4) . . ? O5 C28 C8 112.3(3) . . ? O5 C29 H29A 109.5 . . ? O5 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O5 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C8 N1 C9 113.8(3) . . ? C8 N1 H1 123.1 . . ? C9 N1 H1 123.1 . . ? C17 O2 C18 123.4(3) . . ? C22 O4 C23 121.7(3) . . ? C28 O5 C29 115.6(4) . . ? 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 -0.7(7) . . . . ? Br1 C1 C2 C3 -178.7(3) . . . . ? C1 C2 C3 C4 1.5(6) . . . . ? C2 C3 C4 C5 -1.0(6) . . . . ? C2 C3 C4 C7 176.3(4) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C7 C4 C5 C6 -177.4(3) . . . . ? C2 C1 C6 C5 -0.5(6) . . . . ? Br1 C1 C6 C5 177.4(3) . . . . ? C4 C5 C6 C1 1.0(6) . . . . ? C3 C4 C7 C10 130.2(3) . . . . ? C5 C4 C7 C10 -52.6(4) . . . . ? C3 C4 C7 C8 -112.1(4) . . . . ? C5 C4 C7 C8 65.1(4) . . . . ? C4 C7 C8 N1 -95.4(3) . . . . ? C10 C7 C8 N1 28.2(3) . . . . ? C4 C7 C8 C28 144.0(3) . . . . ? C10 C7 C8 C28 -92.4(3) . . . . ? C4 C7 C8 C27 24.1(5) . . . . ? C10 C7 C8 C27 147.7(3) . . . . ? C4 C7 C10 C22 -23.7(4) . . . . ? C8 C7 C10 C22 -146.2(3) . . . . ? C4 C7 C10 C17 -143.1(3) . . . . ? C8 C7 C10 C17 94.4(3) . . . . ? C4 C7 C10 C9 97.1(3) . . . . ? C8 C7 C10 C9 -25.4(3) . . . . ? N1 C9 C10 C22 135.7(3) . . . . ? C11 C9 C10 C22 -95.5(3) . . . . ? N1 C9 C10 C17 -105.8(3) . . . . ? C11 C9 C10 C17 23.0(4) . . . . ? N1 C9 C10 C7 13.4(3) . . . . ? C11 C9 C10 C7 142.2(3) . . . . ? N1 C9 C11 C12 23.1(5) . . . . ? C10 C9 C11 C12 -100.3(4) . . . . ? N1 C9 C11 C16 -155.8(3) . . . . ? C10 C9 C11 C16 80.8(4) . . . . ? C16 C11 C12 C13 0.7(6) . . . . ? C9 C11 C12 C13 -178.2(4) . . . . ? C11 C12 C13 C14 -1.0(7) . . . . ? C12 C13 C14 C15 -0.4(8) . . . . ? C13 C14 C15 C16 2.1(7) . . . . ? C12 C11 C16 C15 1.0(6) . . . . ? C9 C11 C16 C15 180.0(4) . . . . ? C14 C15 C16 C11 -2.4(7) . . . . ? C22 C10 C17 O1 -145.8(3) . . . . ? C7 C10 C17 O1 -22.7(5) . . . . ? C9 C10 C17 O1 93.3(4) . . . . ? C22 C10 C17 O2 35.9(4) . . . . ? C7 C10 C17 O2 159.0(3) . . . . ? C9 C10 C17 O2 -85.0(3) . . . . ? C17 C10 C22 O3 -116.4(4) . . . . ? C7 C10 C22 O3 122.2(4) . . . . ? C9 C10 C22 O3 4.8(5) . . . . ? C17 C10 C22 O4 63.7(3) . . . . ? C7 C10 C22 O4 -57.8(4) . . . . ? C9 C10 C22 O4 -175.2(3) . . . . ? N1 C8 C28 O6 15.6(5) . . . . ? C27 C8 C28 O6 -102.2(4) . . . . ? C7 C8 C28 O6 132.3(4) . . . . ? N1 C8 C28 O5 -171.2(3) . . . . ? C27 C8 C28 O5 71.0(4) . . . . ? C7 C8 C28 O5 -54.5(4) . . . . ? C28 C8 N1 C9 99.9(3) . . . . ? C27 C8 N1 C9 -144.7(3) . . . . ? C7 C8 N1 C9 -21.3(4) . . . . ? C11 C9 N1 C8 -124.4(3) . . . . ? C10 C9 N1 C8 5.0(4) . . . . ? O1 C17 O2 C18 0.5(6) . . . . ? C10 C17 O2 C18 178.7(3) . . . . ? C21 C18 O2 C17 64.8(4) . . . . ? C20 C18 O2 C17 -177.7(3) . . . . ? C19 C18 O2 C17 -59.8(4) . . . . ? O3 C22 O4 C23 -1.9(5) . . . . ? C10 C22 O4 C23 178.0(3) . . . . ? C26 C23 O4 C22 -58.9(5) . . . . ? C25 C23 O4 C22 -176.9(4) . . . . ? C24 C23 O4 C22 65.0(5) . . . . ? O6 C28 O5 C29 -4.0(6) . . . . ? C8 C28 O5 C29 -177.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.182 _refine_diff_density_min -1.160 _refine_diff_density_rms 0.057