# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email ycheng2@bnu.edu.cn _publ_contact_author_name 'Ying Cheng' loop_ _publ_author_name 'Huan-Rui Pan' 'Xiao-Rong Wang' 'Ying Cheng' # Attachment '5m.CIF' data_m100123b _database_code_depnum_ccdc_archive 'CCDC 791270' #TrackingRef '5m.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H23 Br N2 O6' _chemical_formula_weight 515.35 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 8.5580(12) _cell_length_b 15.813(2) _cell_length_c 16.673(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.473(5) _cell_angle_gamma 90.00 _cell_volume 2231.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 8459 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 1.886 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6602 _exptl_absorpt_correction_T_max 0.7276 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'Rigaku Saturn 724 CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18766 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.93 _reflns_number_total 5327 _reflns_number_gt 4049 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r2' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r2' _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^)+(0.0298P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5327 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _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 0.35267(2) 0.561407(13) 0.208463(11) 0.02276(7) Uani 1 1 d . . . N1 N 0.48713(17) 0.69685(9) 0.64114(8) 0.0134(3) Uani 1 1 d . . . N2 N 0.43508(19) 0.87310(10) 0.49582(9) 0.0195(4) Uani 1 1 d . . . O1 O 0.73751(17) 0.80754(9) 0.51139(8) 0.0185(3) Uani 1 1 d . . . H1 H 0.677(3) 0.8403(14) 0.5014(14) 0.033(8) Uiso 1 1 d . . . O2 O 0.29718(14) 0.53109(8) 0.51358(7) 0.0141(3) Uani 1 1 d . . . O3 O 0.10113(15) 0.40813(8) 0.51534(8) 0.0179(3) Uani 1 1 d . . . O4 O 0.04775(17) 0.43936(8) 0.64061(8) 0.0258(3) Uani 1 1 d . . . O5 O 0.25548(16) 0.52422(9) 0.76839(8) 0.0223(3) Uani 1 1 d . . . O6 O 0.19024(18) 0.65823(9) 0.73472(9) 0.0309(4) Uani 1 1 d . . . C1 C 0.6471(2) 0.73564(11) 0.52876(11) 0.0147(4) Uani 1 1 d . . . H1A H 0.7232 0.6935 0.5571 0.018 Uiso 1 1 calc R . . C2 C 0.5671(2) 0.69381(12) 0.45149(11) 0.0138(4) Uani 1 1 d . . . C3 C 0.6126(2) 0.71672(12) 0.37745(11) 0.0165(4) Uani 1 1 d . . . H3 H 0.6871 0.7611 0.3765 0.020 Uiso 1 1 calc R . . C4 C 0.5531(2) 0.67714(12) 0.30528(11) 0.0170(4) Uani 1 1 d . . . H4 H 0.5876 0.6930 0.2558 0.020 Uiso 1 1 calc R . . C5 C 0.4425(2) 0.61395(12) 0.30721(10) 0.0154(4) Uani 1 1 d . . . C6 C 0.3918(2) 0.58897(11) 0.37829(11) 0.0144(4) Uani 1 1 d . . . H6 H 0.3149 0.5456 0.3779 0.017 Uiso 1 1 calc R . . C7 C 0.4554(2) 0.62861(11) 0.45168(11) 0.0134(4) Uani 1 1 d . . . C8 C 0.3985(2) 0.59967(11) 0.52520(11) 0.0124(4) Uani 1 1 d . . . C9 C 0.4071(2) 0.62841(11) 0.60388(10) 0.0129(4) Uani 1 1 d . . . C10 C 0.5364(2) 0.76383(11) 0.59102(10) 0.0134(4) Uani 1 1 d . . . H10 H 0.6018 0.8029 0.6295 0.016 Uiso 1 1 calc R . . C11 C 0.3983(2) 0.81694(11) 0.55127(10) 0.0133(4) Uani 1 1 d . . . C12 C 0.2474(2) 0.81122(12) 0.57139(12) 0.0179(4) Uani 1 1 d . . . H12 H 0.2255 0.7730 0.6122 0.021 Uiso 1 1 calc R . . C13 C 0.1287(2) 0.86190(12) 0.53134(12) 0.0221(5) Uani 1 1 d . . . H13 H 0.0239 0.8579 0.5435 0.027 Uiso 1 1 calc R . . C14 C 0.1645(2) 0.91820(13) 0.47366(12) 0.0242(5) Uani 1 1 d . . . H14 H 0.0851 0.9533 0.4449 0.029 Uiso 1 1 calc R . . C15 C 0.3196(2) 0.92227(13) 0.45868(12) 0.0251(5) Uani 1 1 d . . . H15 H 0.3450 0.9621 0.4200 0.030 Uiso 1 1 calc R . . C16 C 0.5788(2) 0.68435(12) 0.72292(11) 0.0193(4) Uani 1 1 d . . . H16 H 0.5352 0.6328 0.7464 0.023 Uiso 1 1 calc R . . C17 C 0.7541(2) 0.66746(14) 0.72084(12) 0.0262(5) Uani 1 1 d . . . H17A H 0.7654 0.6173 0.6877 0.039 Uiso 1 1 calc R . . H17B H 0.8080 0.6578 0.7761 0.039 Uiso 1 1 calc R . . H17C H 0.8011 0.7164 0.6974 0.039 Uiso 1 1 calc R . . C18 C 0.5540(3) 0.75817(13) 0.77863(12) 0.0291(5) Uani 1 1 d . . . H18A H 0.5902 0.8106 0.7560 0.044 Uiso 1 1 calc R . . H18B H 0.6143 0.7483 0.8325 0.044 Uiso 1 1 calc R . . H18C H 0.4415 0.7630 0.7831 0.044 Uiso 1 1 calc R . . C19 C 0.1205(2) 0.45125(11) 0.58546(12) 0.0178(4) Uani 1 1 d . . . C20 C 0.2419(2) 0.51699(11) 0.58529(11) 0.0145(4) Uani 1 1 d . . . C21 C 0.3028(2) 0.57418(11) 0.64161(11) 0.0135(4) Uani 1 1 d . . . C22 C 0.2447(2) 0.59098(12) 0.71956(11) 0.0173(4) Uani 1 1 d . . . C23 C -0.0050(2) 0.33673(12) 0.51125(12) 0.0226(5) Uani 1 1 d . . . H23A H 0.0483 0.2892 0.5416 0.034 Uiso 1 1 calc R . . H23B H -0.0359 0.3202 0.4545 0.034 Uiso 1 1 calc R . . H23C H -0.0993 0.3523 0.5348 0.034 Uiso 1 1 calc R . . C24 C 0.1768(3) 0.53310(14) 0.83904(14) 0.0388(7) Uani 1 1 d . . . H24A H 0.2380 0.5711 0.8781 0.058 Uiso 1 1 calc R . . H24B H 0.1681 0.4776 0.8641 0.058 Uiso 1 1 calc R . . H24C H 0.0709 0.5567 0.8228 0.058 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 0.02956(12) 0.02404(12) 0.01409(11) -0.00387(9) 0.00125(8) -0.00050(9) N1 0.0168(8) 0.0117(8) 0.0115(8) -0.0007(6) 0.0018(6) -0.0025(6) N2 0.0220(9) 0.0175(9) 0.0199(9) 0.0044(7) 0.0062(7) 0.0035(7) O1 0.0155(8) 0.0165(8) 0.0241(8) -0.0004(6) 0.0049(6) -0.0048(6) O2 0.0170(7) 0.0119(7) 0.0144(7) -0.0001(5) 0.0055(5) -0.0023(5) O3 0.0181(7) 0.0129(7) 0.0233(7) -0.0026(6) 0.0053(6) -0.0036(5) O4 0.0290(8) 0.0268(8) 0.0244(8) 0.0015(7) 0.0129(7) -0.0093(6) O5 0.0313(9) 0.0198(8) 0.0180(7) 0.0062(6) 0.0107(6) 0.0059(6) O6 0.0495(10) 0.0176(8) 0.0311(9) 0.0024(7) 0.0243(8) 0.0096(7) C1 0.0140(10) 0.0132(10) 0.0174(10) 0.0007(8) 0.0040(7) -0.0016(7) C2 0.0129(10) 0.0139(10) 0.0151(9) -0.0014(8) 0.0033(7) 0.0030(7) C3 0.0147(10) 0.0157(10) 0.0196(10) 0.0034(8) 0.0047(8) -0.0015(8) C4 0.0186(10) 0.0195(11) 0.0140(9) 0.0029(8) 0.0055(8) 0.0015(8) C5 0.0182(10) 0.0153(10) 0.0123(9) -0.0026(8) 0.0005(7) 0.0033(8) C6 0.0150(10) 0.0118(9) 0.0165(10) 0.0002(8) 0.0024(7) -0.0004(7) C7 0.0130(9) 0.0133(10) 0.0143(9) 0.0016(8) 0.0034(7) 0.0038(7) C8 0.0124(9) 0.0092(9) 0.0158(9) -0.0006(7) 0.0030(7) -0.0019(7) C9 0.0133(10) 0.0105(9) 0.0150(9) 0.0004(8) 0.0025(7) 0.0027(7) C10 0.0149(10) 0.0114(9) 0.0142(9) -0.0007(7) 0.0033(7) -0.0020(7) C11 0.0169(10) 0.0102(9) 0.0129(9) -0.0027(7) 0.0027(7) -0.0009(7) C12 0.0182(10) 0.0127(10) 0.0230(10) -0.0014(8) 0.0038(8) -0.0011(8) C13 0.0159(11) 0.0181(11) 0.0328(12) -0.0048(9) 0.0051(9) 0.0004(8) C14 0.0242(12) 0.0231(12) 0.0245(11) 0.0023(9) 0.0008(9) 0.0083(9) C15 0.0306(13) 0.0237(12) 0.0218(11) 0.0085(9) 0.0072(9) 0.0066(9) C16 0.0228(11) 0.0204(11) 0.0140(10) 0.0025(8) -0.0001(8) -0.0034(8) C17 0.0262(12) 0.0268(12) 0.0234(11) 0.0035(9) -0.0042(9) -0.0015(9) C18 0.0396(14) 0.0310(13) 0.0167(10) -0.0065(9) 0.0046(9) -0.0082(10) C19 0.0165(10) 0.0136(10) 0.0228(11) 0.0018(8) 0.0012(8) 0.0008(8) C20 0.0160(10) 0.0135(10) 0.0152(9) 0.0038(8) 0.0056(8) 0.0017(7) C21 0.0166(10) 0.0102(9) 0.0143(9) 0.0012(7) 0.0049(7) 0.0020(7) C22 0.0180(10) 0.0164(10) 0.0180(10) 0.0007(8) 0.0050(8) -0.0017(8) C23 0.0193(11) 0.0134(10) 0.0347(12) -0.0027(9) 0.0022(9) -0.0047(8) C24 0.0589(17) 0.0370(14) 0.0269(13) 0.0113(11) 0.0271(12) 0.0123(12) _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 C5 1.9023(18) . ? N1 C9 1.379(2) . ? N1 C10 1.450(2) . ? N1 C16 1.483(2) . ? N2 C15 1.336(2) . ? N2 C11 1.352(2) . ? O1 C1 1.429(2) . ? O1 H1 0.73(2) . ? O2 C20 1.367(2) . ? O2 C8 1.384(2) . ? O3 C19 1.342(2) . ? O3 C23 1.444(2) . ? O4 C19 1.199(2) . ? O5 C22 1.328(2) . ? O5 C24 1.447(2) . ? O6 C22 1.203(2) . ? C1 C2 1.519(3) . ? C1 C10 1.570(2) . ? C1 H1A 1.0000 . ? C2 C3 1.396(2) . ? C2 C7 1.406(2) . ? C3 C4 1.385(3) . ? C3 H3 0.9500 . ? C4 C5 1.380(2) . ? C4 H4 0.9500 . ? C5 C6 1.378(2) . ? C6 C7 1.411(2) . ? C6 H6 0.9500 . ? C7 C8 1.458(2) . ? C8 C9 1.380(2) . ? C9 C21 1.447(2) . ? C10 C11 1.520(2) . ? C10 H10 1.0000 . ? C11 C12 1.384(2) . ? C12 C13 1.386(3) . ? C12 H12 0.9500 . ? C13 C14 1.378(3) . ? C13 H13 0.9500 . ? C14 C15 1.388(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C18 1.526(3) . ? C16 C17 1.529(3) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.470(2) . ? C20 C21 1.351(3) . ? C21 C22 1.482(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C10 118.75(14) . . ? C9 N1 C16 118.04(15) . . ? C10 N1 C16 117.90(15) . . ? C15 N2 C11 117.93(16) . . ? C1 O1 H1 103.0(19) . . ? C20 O2 C8 107.19(13) . . ? C19 O3 C23 115.75(14) . . ? C22 O5 C24 115.03(15) . . ? O1 C1 C2 111.39(14) . . ? O1 C1 C10 107.81(14) . . ? C2 C1 C10 116.37(15) . . ? O1 C1 H1A 106.9 . . ? C2 C1 H1A 106.9 . . ? C10 C1 H1A 106.9 . . ? C3 C2 C7 118.08(17) . . ? C3 C2 C1 119.16(16) . . ? C7 C2 C1 122.63(15) . . ? C4 C3 C2 122.42(17) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C5 C4 C3 118.19(16) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C6 C5 C4 122.10(17) . . ? C6 C5 Br1 118.74(14) . . ? C4 C5 Br1 119.15(13) . . ? C5 C6 C7 119.23(17) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C2 C7 C6 119.96(16) . . ? C2 C7 C8 122.92(17) . . ? C6 C7 C8 117.11(16) . . ? C9 C8 O2 109.63(14) . . ? C9 C8 C7 135.90(17) . . ? O2 C8 C7 114.10(15) . . ? N1 C9 C8 129.83(15) . . ? N1 C9 C21 124.50(15) . . ? C8 C9 C21 105.55(16) . . ? N1 C10 C11 112.43(14) . . ? N1 C10 C1 115.40(14) . . ? C11 C10 C1 112.01(14) . . ? N1 C10 H10 105.3 . . ? C11 C10 H10 105.3 . . ? C1 C10 H10 105.3 . . ? N2 C11 C12 121.87(17) . . ? N2 C11 C10 114.63(15) . . ? C12 C11 C10 123.46(16) . . ? C11 C12 C13 119.30(17) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C14 C13 C12 119.18(18) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 118.19(19) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? N2 C15 C14 123.47(18) . . ? N2 C15 H15 118.3 . . ? C14 C15 H15 118.3 . . ? N1 C16 C18 110.82(16) . . ? N1 C16 C17 112.98(14) . . ? C18 C16 C17 111.87(17) . . ? N1 C16 H16 106.9 . . ? C18 C16 H16 106.9 . . ? C17 C16 H16 106.9 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O4 C19 O3 125.21(18) . . ? O4 C19 C20 124.03(18) . . ? O3 C19 C20 110.75(15) . . ? C21 C20 O2 110.55(15) . . ? C21 C20 C19 132.21(16) . . ? O2 C20 C19 116.91(16) . . ? C20 C21 C9 107.08(15) . . ? C20 C21 C22 125.77(16) . . ? C9 C21 C22 125.67(16) . . ? O6 C22 O5 124.62(16) . . ? O6 C22 C21 122.22(17) . . ? O5 C22 C21 113.14(16) . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O5 C24 H24A 109.5 . . ? O5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 12.6(2) . . . . ? C10 C1 C2 C3 136.67(17) . . . . ? O1 C1 C2 C7 -171.65(16) . . . . ? C10 C1 C2 C7 -47.5(2) . . . . ? C7 C2 C3 C4 -0.7(3) . . . . ? C1 C2 C3 C4 175.32(16) . . . . ? C2 C3 C4 C5 1.3(3) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C3 C4 C5 Br1 177.62(14) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? Br1 C5 C6 C7 -178.82(13) . . . . ? C3 C2 C7 C6 -0.6(3) . . . . ? C1 C2 C7 C6 -176.40(16) . . . . ? C3 C2 C7 C8 -179.68(17) . . . . ? C1 C2 C7 C8 4.5(3) . . . . ? C5 C6 C7 C2 1.1(3) . . . . ? C5 C6 C7 C8 -179.74(16) . . . . ? C20 O2 C8 C9 0.13(19) . . . . ? C20 O2 C8 C7 -173.98(15) . . . . ? C2 C7 C8 C9 12.2(3) . . . . ? C6 C7 C8 C9 -166.9(2) . . . . ? C2 C7 C8 O2 -175.78(16) . . . . ? C6 C7 C8 O2 5.1(2) . . . . ? C10 N1 C9 C8 19.1(3) . . . . ? C16 N1 C9 C8 -134.63(19) . . . . ? C10 N1 C9 C21 -156.29(17) . . . . ? C16 N1 C9 C21 49.9(2) . . . . ? O2 C8 C9 N1 -176.82(17) . . . . ? C7 C8 C9 N1 -4.6(4) . . . . ? O2 C8 C9 C21 -0.72(19) . . . . ? C7 C8 C9 C21 171.5(2) . . . . ? C9 N1 C10 C11 72.12(19) . . . . ? C16 N1 C10 C11 -134.07(16) . . . . ? C9 N1 C10 C1 -58.0(2) . . . . ? C16 N1 C10 C1 95.78(18) . . . . ? O1 C1 C10 N1 -154.96(15) . . . . ? C2 C1 C10 N1 79.1(2) . . . . ? O1 C1 C10 C11 74.68(19) . . . . ? C2 C1 C10 C11 -51.2(2) . . . . ? C15 N2 C11 C12 -1.8(3) . . . . ? C15 N2 C11 C10 -179.68(17) . . . . ? N1 C10 C11 N2 -171.84(15) . . . . ? C1 C10 C11 N2 -40.0(2) . . . . ? N1 C10 C11 C12 10.3(2) . . . . ? C1 C10 C11 C12 142.14(17) . . . . ? N2 C11 C12 C13 2.7(3) . . . . ? C10 C11 C12 C13 -179.54(17) . . . . ? C11 C12 C13 C14 -1.5(3) . . . . ? C12 C13 C14 C15 -0.6(3) . . . . ? C11 N2 C15 C14 -0.5(3) . . . . ? C13 C14 C15 N2 1.7(3) . . . . ? C9 N1 C16 C18 -137.00(16) . . . . ? C10 N1 C16 C18 69.01(19) . . . . ? C9 N1 C16 C17 96.55(19) . . . . ? C10 N1 C16 C17 -57.4(2) . . . . ? C23 O3 C19 O4 -6.6(3) . . . . ? C23 O3 C19 C20 174.57(15) . . . . ? C8 O2 C20 C21 0.6(2) . . . . ? C8 O2 C20 C19 174.78(16) . . . . ? O4 C19 C20 C21 2.3(3) . . . . ? O3 C19 C20 C21 -178.83(19) . . . . ? O4 C19 C20 O2 -170.35(18) . . . . ? O3 C19 C20 O2 8.5(2) . . . . ? O2 C20 C21 C9 -1.0(2) . . . . ? C19 C20 C21 C9 -174.0(2) . . . . ? O2 C20 C21 C22 165.69(17) . . . . ? C19 C20 C21 C22 -7.3(3) . . . . ? N1 C9 C21 C20 177.41(17) . . . . ? C8 C9 C21 C20 1.0(2) . . . . ? N1 C9 C21 C22 10.7(3) . . . . ? C8 C9 C21 C22 -165.67(18) . . . . ? C24 O5 C22 O6 8.0(3) . . . . ? C24 O5 C22 C21 -170.24(18) . . . . ? C20 C21 C22 O6 -116.3(2) . . . . ? C9 C21 C22 O6 48.0(3) . . . . ? C20 C21 C22 O5 61.9(3) . . . . ? C9 C21 C22 O5 -133.77(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N2 0.73(2) 2.13(2) 2.765(2) 146(2) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.343 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.074 # Attachment '6m.cif' #1.Name of contact person #Ying Cheng #2.E-mail address of contact person #ycheng2@bnu.edu.cn #3.Authors'names #Huan-Rui Pan, Xiao-Rong Wang, Ying Cheng #4.Name of the journal to which the paper will be submitted #Org. Biomol. Chem. #5. Compound name #(5S,6R)-Dimethyl 8-bromo-6-hydroxyl-4-isopropyl-5-(2-pyridyl)- #5,6-dihydrobenzo[d]furo[3,2-b]azepine-2,3-dicarboxylate #6. Compound synonym #7. Formula C24 H23 Br N2 O6 #8. Formula weight 515.35 #9. Colour Colourless #10. Melting point 140-141 oC #11.Crystallization solvent acetone, ethyl ether and n-butane data_101126b_0m _database_code_depnum_ccdc_archive 'CCDC 802475' #TrackingRef '6m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ?(5S,6R)-Dimethyl 8-bromo-6-hydroxyl-4-isopropyl-5-(2-pyridyl)- 5,6-dihydrobenzo[d]furo[3,2-b]azepine-2,3-dicarboxylate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H23 Br N2 O6' _chemical_formula_sum 'C24 H23 Br N2 O6' _chemical_formula_weight 515.35 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 Tetragonal _symmetry_space_group_name_H-M P-4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' _cell_length_a 29.5080(10) _cell_length_b 29.5080(10) _cell_length_c 12.1390(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10569.7(10) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9899 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 21.81 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4224 _exptl_absorpt_coefficient_mu 1.593 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5277 _exptl_absorpt_correction_T_max 0.5682 _exptl_absorpt_process_details SADABS _exptl_special_details ; Melting point 140-141 oC Crystallization solvent acetone, ethyl ether and n-butane ; _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 19871 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0680 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.64 _reflns_number_total 19871 _reflns_number_gt 14156 _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^)+(0.0488P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.003(5) _refine_ls_number_reflns 19871 _refine_ls_number_parameters 1231 _refine_ls_number_restraints 1280 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0964 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.500 47 3 ' ' 2 0.000 0.500 0.978 40 6 ' ' 3 0.251 0.259 0.258 381 48 ' ' 4 0.259 0.749 0.742 381 48 ' ' 5 0.500 0.000 0.022 40 6 ' ' 6 0.500 0.500 0.500 50 6 ' ' 7 0.749 0.741 0.258 381 48 ' ' 8 0.741 0.251 0.742 381 48 ' ' _platon_squeeze_details ; ; 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 0.416605(13) 0.382435(12) 0.51428(3) 0.05712(10) Uani 1 1 d . . . Br2 Br 0.390846(15) 0.087827(14) -0.01019(3) 0.07042(11) Uani 1 1 d . . . Br3 Br 0.090561(14) 0.105897(14) 1.50948(3) 0.06906(12) Uani 1 1 d . . . Br4 Br 0.109056(15) 0.404737(18) 0.02364(3) 0.08364(14) Uani 1 1 d . . . C1 C 0.40905(10) 0.41299(11) 0.3779(2) 0.0402(8) Uani 1 1 d U . . C2 C 0.41004(10) 0.38851(10) 0.2828(2) 0.0374(7) Uani 1 1 d U . . H2 H 0.4145 0.3573 0.2859 0.045 Uiso 1 1 calc R . . C3 C 0.40443(9) 0.40961(9) 0.1811(2) 0.0322(7) Uani 1 1 d U . . C4 C 0.39742(9) 0.45699(9) 0.1777(2) 0.0340(7) Uani 1 1 d U . . C5 C 0.39535(11) 0.47989(11) 0.2780(3) 0.0472(9) Uani 1 1 d U . . H5 H 0.3894 0.5108 0.2773 0.057 Uiso 1 1 calc R . . C6 C 0.40165(12) 0.45906(11) 0.3778(3) 0.0509(9) Uani 1 1 d U . . H6 H 0.4010 0.4755 0.4432 0.061 Uiso 1 1 calc R . . C7 C 0.40543(10) 0.38252(9) 0.0813(2) 0.0325(7) Uani 1 1 d U . . C8 C 0.41492(10) 0.31667(9) 0.0012(2) 0.0417(7) Uani 1 1 d U . . C9 C 0.42689(13) 0.26782(10) -0.0050(3) 0.0552(9) Uani 1 1 d U . . C10 C 0.4621(2) 0.20665(13) 0.0876(4) 0.137(3) Uani 1 1 d U . . H10A H 0.4377 0.1884 0.0597 0.205 Uiso 1 1 calc R . . H10B H 0.4686 0.1980 0.1622 0.205 Uiso 1 1 calc R . . H10C H 0.4886 0.2021 0.0430 0.205 Uiso 1 1 calc R . . C11 C 0.39945(10) 0.34380(10) -0.0776(2) 0.0342(7) Uani 1 1 d U . . C12 C 0.38863(12) 0.32851(10) -0.1913(3) 0.0443(8) Uani 1 1 d U . . C13 C 0.32888(15) 0.30469(17) -0.3092(4) 0.0923(15) Uani 1 1 d U . . H13A H 0.3280 0.3298 -0.3594 0.138 Uiso 1 1 calc R . . H13B H 0.2991 0.2920 -0.3022 0.138 Uiso 1 1 calc R . . H13C H 0.3493 0.2820 -0.3367 0.138 Uiso 1 1 calc R . . C14 C 0.39351(9) 0.38792(9) -0.0282(3) 0.0321(7) Uani 1 1 d U . . C15 C 0.38321(12) 0.43351(11) -0.1978(3) 0.0526(9) Uani 1 1 d U . . H15 H 0.3966 0.4057 -0.2273 0.063 Uiso 1 1 calc R . . C16 C 0.33777(16) 0.43900(17) -0.2531(4) 0.1015(17) Uani 1 1 d U . . H16A H 0.3172 0.4165 -0.2256 0.152 Uiso 1 1 calc R . . H16B H 0.3412 0.4353 -0.3313 0.152 Uiso 1 1 calc R . . H16C H 0.3260 0.4687 -0.2377 0.152 Uiso 1 1 calc R . . C17 C 0.41585(17) 0.47184(13) -0.2255(3) 0.0835(14) Uani 1 1 d U . . H17A H 0.4043 0.4998 -0.1965 0.125 Uiso 1 1 calc R . . H17B H 0.4189 0.4743 -0.3040 0.125 Uiso 1 1 calc R . . H17C H 0.4449 0.4656 -0.1933 0.125 Uiso 1 1 calc R . . C18 C 0.35910(9) 0.46330(9) -0.0115(3) 0.0381(7) Uani 1 1 d U . . H18 H 0.3524 0.4879 -0.0632 0.046 Uiso 1 1 calc R . . C19 C 0.31426(10) 0.45155(12) 0.0420(3) 0.0499(9) Uani 1 1 d U . . C20 C 0.29097(14) 0.41230(15) 0.0235(5) 0.1035(18) Uani 1 1 d U . . H20 H 0.3018 0.3907 -0.0258 0.124 Uiso 1 1 calc R . . C21 C 0.25051(16) 0.40535(19) 0.0804(6) 0.143(3) Uani 1 1 d U . . H21 H 0.2337 0.3791 0.0692 0.172 Uiso 1 1 calc R . . C22 C 0.23578(16) 0.43795(18) 0.1535(5) 0.113(2) Uani 1 1 d U . . H22 H 0.2095 0.4339 0.1947 0.135 Uiso 1 1 calc R . . C23 C 0.26084(13) 0.47581(16) 0.1629(4) 0.0809(13) Uani 1 1 d U . . H23 H 0.2502 0.4986 0.2090 0.097 Uiso 1 1 calc R . . C24 C 0.39262(10) 0.48348(10) 0.0728(2) 0.0356(7) Uani 1 1 d U . . H24 H 0.3799 0.5129 0.0943 0.043 Uiso 1 1 calc R . . C25 C 0.42386(12) 0.09491(11) 0.1241(3) 0.0467(8) Uani 1 1 d U . . C26 C 0.40026(12) 0.10068(10) 0.2185(2) 0.0443(8) Uani 1 1 d U . . H26 H 0.3688 0.1019 0.2163 0.053 Uiso 1 1 calc R . . C27 C 0.42294(10) 0.10486(9) 0.3205(2) 0.0370(7) Uani 1 1 d U . . C28 C 0.46988(10) 0.10380(9) 0.3211(3) 0.0398(8) Uani 1 1 d U . . C29 C 0.49279(13) 0.09897(11) 0.2192(3) 0.0563(10) Uani 1 1 d U . . H29 H 0.5243 0.0993 0.2184 0.068 Uiso 1 1 calc R . . C30 C 0.47008(13) 0.09383(12) 0.1226(3) 0.0571(10) Uani 1 1 d U . . H30 H 0.4857 0.0897 0.0569 0.069 Uiso 1 1 calc R . . C31 C 0.39608(10) 0.11060(11) 0.4190(3) 0.0396(8) Uani 1 1 d U . . C32 C 0.32886(10) 0.11660(11) 0.4968(3) 0.0512(8) Uani 1 1 d U . . C33 C 0.27931(11) 0.11838(13) 0.5002(3) 0.0631(10) Uani 1 1 d U . . C34 C 0.21213(14) 0.1124(2) 0.3984(5) 0.142(3) Uani 1 1 d U . . H34A H 0.2010 0.1343 0.4500 0.213 Uiso 1 1 calc R . . H34B H 0.2009 0.0829 0.4177 0.213 Uiso 1 1 calc R . . H34C H 0.2020 0.1201 0.3256 0.213 Uiso 1 1 calc R . . C35 C 0.35944(11) 0.12109(10) 0.5793(3) 0.0421(8) Uani 1 1 d U . . C36 C 0.34602(10) 0.12969(12) 0.6967(3) 0.0433(8) Uani 1 1 d U . . C37 C 0.32662(16) 0.18665(14) 0.8241(4) 0.0844(14) Uani 1 1 d U . . H37A H 0.2963 0.1759 0.8353 0.127 Uiso 1 1 calc R . . H37B H 0.3272 0.2190 0.8314 0.127 Uiso 1 1 calc R . . H37C H 0.3463 0.1733 0.8779 0.127 Uiso 1 1 calc R . . C38 C 0.40332(10) 0.11665(9) 0.5301(3) 0.0346(7) Uani 1 1 d U . . C39 C 0.45084(11) 0.10835(12) 0.6990(3) 0.0487(9) Uani 1 1 d U . . H39 H 0.4211 0.0986 0.7264 0.058 Uiso 1 1 calc R . . C40 C 0.46471(15) 0.14971(14) 0.7670(3) 0.0762(12) Uani 1 1 d U . . H40A H 0.4941 0.1599 0.7437 0.114 Uiso 1 1 calc R . . H40B H 0.4658 0.1416 0.8436 0.114 Uiso 1 1 calc R . . H40C H 0.4430 0.1735 0.7565 0.114 Uiso 1 1 calc R . . C41 C 0.48327(12) 0.06872(13) 0.7166(3) 0.0626(10) Uani 1 1 d U . . H41A H 0.4740 0.0436 0.6716 0.094 Uiso 1 1 calc R . . H41B H 0.4828 0.0599 0.7927 0.094 Uiso 1 1 calc R . . H41C H 0.5134 0.0777 0.6966 0.094 Uiso 1 1 calc R . . C42 C 0.48308(10) 0.13584(9) 0.5184(3) 0.0412(7) Uani 1 1 d U . . H42 H 0.5086 0.1364 0.5700 0.049 Uiso 1 1 calc R . . C43 C 0.47727(10) 0.18454(10) 0.4793(3) 0.0475(8) Uani 1 1 d U . . C44 C 0.44814(14) 0.21408(12) 0.5286(4) 0.0822(14) Uani 1 1 d U . . H44 H 0.4288 0.2040 0.5840 0.099 Uiso 1 1 calc R . . C45 C 0.44722(16) 0.25858(14) 0.4970(5) 0.1089(19) Uani 1 1 d U . . H45 H 0.4290 0.2795 0.5333 0.131 Uiso 1 1 calc R . . C46 C 0.47408(16) 0.27158(13) 0.4099(4) 0.0960(16) Uani 1 1 d U . . H46 H 0.4728 0.3010 0.3824 0.115 Uiso 1 1 calc R . . C47 C 0.50267(15) 0.24011(14) 0.3646(4) 0.0815(14) Uani 1 1 d U . . H47 H 0.5214 0.2491 0.3070 0.098 Uiso 1 1 calc R . . C48 C 0.49821(11) 0.10450(10) 0.4229(3) 0.0434(8) Uani 1 1 d U . . H48 H 0.5284 0.1149 0.4004 0.052 Uiso 1 1 calc R . . C49 C 0.05906(12) 0.10570(11) 1.3739(3) 0.0509(9) Uani 1 1 d U . . C50 C 0.08201(11) 0.11482(10) 1.2787(3) 0.0436(8) Uani 1 1 d U . . H50 H 0.1130 0.1204 1.2816 0.052 Uiso 1 1 calc R . . C51 C 0.05972(10) 0.11596(10) 1.1771(3) 0.0410(8) Uani 1 1 d U . . C52 C 0.01329(11) 0.10886(10) 1.1734(3) 0.0447(8) Uani 1 1 d U . . C53 C -0.00983(12) 0.10061(12) 1.2723(3) 0.0594(11) Uani 1 1 d U . . H53 H -0.0410 0.0963 1.2705 0.071 Uiso 1 1 calc R . . C54 C 0.01242(13) 0.09873(12) 1.3724(3) 0.0640(11) Uani 1 1 d U . . H54 H -0.0034 0.0929 1.4371 0.077 Uiso 1 1 calc R . . C55 C 0.08648(11) 0.12530(11) 1.0794(3) 0.0431(8) Uani 1 1 d U A . C56 C 0.15310(10) 0.13793(11) 1.0046(3) 0.0525(9) Uani 1 1 d U A . C57 C 0.20280(12) 0.14163(15) 1.0033(3) 0.0701(11) Uani 1 1 d U . . C58 C 0.26984(14) 0.1239(3) 1.0984(5) 0.155(3) Uani 1 1 d U . . H58A H 0.2818 0.1372 1.0324 0.233 Uiso 1 1 calc R . . H58B H 0.2804 0.0932 1.1046 0.233 Uiso 1 1 calc R . . H58C H 0.2798 0.1410 1.1611 0.233 Uiso 1 1 calc R . . C59 C 0.12205(11) 0.14497(12) 0.9243(3) 0.0505(9) Uani 1 1 d U . . C60 C 0.1388(2) 0.1506(2) 0.8018(6) 0.0563(17) Uani 0.659(3) 1 d PU A 1 C61 C 0.1656(3) 0.2052(3) 0.6804(7) 0.111(3) Uani 0.659(3) 1 d PU A 1 H61A H 0.1662 0.2373 0.6686 0.166 Uiso 0.659(3) 1 calc PR A 1 H61B H 0.1483 0.1910 0.6230 0.166 Uiso 0.659(3) 1 calc PR A 1 H61C H 0.1960 0.1936 0.6794 0.166 Uiso 0.659(3) 1 calc PR A 1 C62 C 0.07837(10) 0.13634(10) 0.9717(3) 0.0450(8) Uani 1 1 d U A . C63 C 0.03240(13) 0.13850(15) 0.7993(3) 0.0710(11) Uani 1 1 d U A . H63 H 0.0627 0.1324 0.7700 0.085 Uiso 1 1 calc R . . C64 C 0.0177(2) 0.1836(2) 0.7522(4) 0.130(2) Uani 1 1 d U . . H64A H -0.0139 0.1882 0.7672 0.195 Uiso 1 1 calc R . . H64B H 0.0226 0.1837 0.6741 0.195 Uiso 1 1 calc R . . H64C H 0.0351 0.2074 0.7856 0.195 Uiso 1 1 calc R . . C65 C 0.00267(15) 0.0993(2) 0.7633(4) 0.1129(19) Uani 1 1 d U . . H65A H 0.0145 0.0716 0.7928 0.169 Uiso 1 1 calc R . . H65B H 0.0023 0.0977 0.6843 0.169 Uiso 1 1 calc R . . H65C H -0.0276 0.1040 0.7899 0.169 Uiso 1 1 calc R . . C66 C -0.00379(10) 0.14676(10) 0.9850(3) 0.0457(8) Uani 1 1 d U A . H66 H -0.0289 0.1459 0.9323 0.055 Uiso 1 1 calc R . . C67 C -0.00643(11) 0.19316(11) 1.0400(3) 0.0490(8) Uani 1 1 d U . . C68 C 0.02522(14) 0.22630(12) 1.0290(4) 0.0735(12) Uani 1 1 d U . . H68 H 0.0514 0.2214 0.9880 0.088 Uiso 1 1 calc R . . C69 C 0.01783(17) 0.26690(14) 1.0795(4) 0.0898(15) Uani 1 1 d U . . H69 H 0.0391 0.2900 1.0728 0.108 Uiso 1 1 calc R . . C70 C -0.02019(18) 0.27366(16) 1.1390(4) 0.0951(15) Uani 1 1 d U . . H70 H -0.0255 0.3013 1.1733 0.114 Uiso 1 1 calc R . . C71 C -0.05095(15) 0.23881(15) 1.1481(4) 0.0855(14) Uani 1 1 d U . . H71 H -0.0768 0.2429 1.1908 0.103 Uiso 1 1 calc R . . C72 C -0.01350(10) 0.10848(11) 1.0691(3) 0.0462(9) Uani 1 1 d U . . H72 H -0.0452 0.1124 1.0913 0.055 Uiso 1 1 calc R . . C73 C 0.07738(12) 0.39711(12) 0.1595(3) 0.0523(9) Uani 1 1 d U . . C74 C 0.10225(11) 0.39436(11) 0.2547(3) 0.0449(8) Uani 1 1 d U . . H74 H 0.1337 0.3955 0.2518 0.054 Uiso 1 1 calc R . . C75 C 0.08021(10) 0.38985(9) 0.3564(3) 0.0359(7) Uani 1 1 d U . . C76 C 0.03320(10) 0.38696(10) 0.3589(3) 0.0402(7) Uani 1 1 d U . . C77 C 0.00974(11) 0.38795(12) 0.2584(3) 0.0504(9) Uani 1 1 d U . . H77 H -0.0216 0.3844 0.2590 0.060 Uiso 1 1 calc R . . C78 C 0.03129(12) 0.39393(12) 0.1589(3) 0.0574(10) Uani 1 1 d U . . H78 H 0.0150 0.3958 0.0935 0.069 Uiso 1 1 calc R . . C79 C 0.10814(10) 0.38716(10) 0.4537(2) 0.0377(7) Uani 1 1 d U B . C80 C 0.17592(10) 0.38785(12) 0.5298(3) 0.0508(8) Uani 1 1 d U B . C81 C 0.22537(12) 0.39157(13) 0.5310(3) 0.0611(10) Uani 1 1 d U . . C82 C 0.28985(14) 0.4076(2) 0.4265(4) 0.140(3) Uani 1 1 d U . . H82A H 0.3007 0.4336 0.4664 0.210 Uiso 1 1 calc R . . H82B H 0.2984 0.4103 0.3505 0.210 Uiso 1 1 calc R . . H82C H 0.3029 0.3806 0.4571 0.210 Uiso 1 1 calc R . . C83 C 0.14712(11) 0.37697(11) 0.6116(3) 0.0452(8) Uani 1 1 d U B . C84 C 0.16323(12) 0.36712(14) 0.7257(3) 0.0582(10) Uani 1 1 d DU . . C85 C 0.1948(5) 0.3149(5) 0.8465(9) 0.161(5) Uani 0.729(13) 1 d PDU B 1 H85A H 0.2049 0.2840 0.8491 0.242 Uiso 0.729(13) 1 calc PR B 1 H85B H 0.1721 0.3197 0.9019 0.242 Uiso 0.729(13) 1 calc PR B 1 H85C H 0.2200 0.3348 0.8597 0.242 Uiso 0.729(13) 1 calc PR B 1 O22 O 0.1753(3) 0.32465(17) 0.7359(5) 0.0769(18) Uani 0.729(13) 1 d PDU B 1 C85' C 0.1738(15) 0.3027(14) 0.859(2) 0.161(5) Uani 0.271(13) 1 d PDU B 2 H85D H 0.1715 0.2703 0.8524 0.242 Uiso 0.271(13) 1 calc PR B 2 H85E H 0.1543 0.3130 0.9170 0.242 Uiso 0.271(13) 1 calc PR B 2 H85F H 0.2046 0.3108 0.8757 0.242 Uiso 0.271(13) 1 calc PR B 2 O22' O 0.1599(8) 0.3245(5) 0.7518(17) 0.0769(18) Uani 0.271(13) 1 d PDU B 2 C86 C 0.10217(10) 0.37665(10) 0.5639(3) 0.0401(8) Uani 1 1 d U . . C87 C 0.05764(13) 0.36873(14) 0.7345(3) 0.0648(11) Uani 1 1 d U . . H87 H 0.0863 0.3809 0.7627 0.078 Uiso 1 1 calc R B . C88 C 0.0517(2) 0.32209(19) 0.7849(4) 0.128(2) Uani 1 1 d U B . H88A H 0.0227 0.3101 0.7642 0.193 Uiso 1 1 calc R . . H88B H 0.0535 0.3243 0.8636 0.193 Uiso 1 1 calc R . . H88C H 0.0752 0.3024 0.7586 0.193 Uiso 1 1 calc R . . C89 C 0.02034(15) 0.4014(2) 0.7696(4) 0.1043(18) Uani 1 1 d U B . H89A H 0.0253 0.4303 0.7355 0.156 Uiso 1 1 calc R . . H89B H 0.0208 0.4048 0.8482 0.156 Uiso 1 1 calc R . . H89C H -0.0085 0.3896 0.7471 0.156 Uiso 1 1 calc R . . C90 C 0.02334(11) 0.35104(10) 0.5518(3) 0.0448(8) Uani 1 1 d U . . H90 H -0.0014 0.3488 0.6053 0.054 Uiso 1 1 calc R B . C91 C 0.02740(11) 0.30397(10) 0.5026(3) 0.0503(8) Uani 1 1 d U B . C92 C 0.06650(14) 0.27955(12) 0.4977(4) 0.0831(14) Uani 1 1 d U . . H92 H 0.0931 0.2908 0.5282 0.100 Uiso 1 1 calc R B . C93 C 0.06585(19) 0.23713(15) 0.4458(6) 0.113(2) Uani 1 1 d U B . H93 H 0.0923 0.2202 0.4399 0.136 Uiso 1 1 calc R . . C94 C 0.02707(19) 0.22136(14) 0.4052(5) 0.1014(17) Uani 1 1 d U . . H94 H 0.0261 0.1934 0.3701 0.122 Uiso 1 1 calc R B . C95 C -0.01115(17) 0.24681(15) 0.4157(4) 0.0886(14) Uani 1 1 d U B . H95 H -0.0384 0.2353 0.3890 0.106 Uiso 1 1 calc R . . C96 C 0.00602(10) 0.38454(10) 0.4632(3) 0.0435(8) Uani 1 1 d U B . H96 H -0.0240 0.3736 0.4416 0.052 Uiso 1 1 calc R . . C60' C 0.1305(5) 0.1738(5) 0.8318(11) 0.0563(17) Uani 0.341(3) 1 d PU A 2 C61' C 0.1741(7) 0.1761(6) 0.6645(15) 0.111(3) Uani 0.341(3) 1 d PU A 2 H61D H 0.1894 0.1546 0.6184 0.166 Uiso 0.341(3) 1 calc PR A 2 H61E H 0.1956 0.1980 0.6912 0.166 Uiso 0.341(3) 1 calc PR A 2 H61F H 0.1511 0.1913 0.6228 0.166 Uiso 0.341(3) 1 calc PR A 2 N1 N 0.37798(8) 0.42667(8) -0.0786(2) 0.0388(6) Uani 1 1 d . . . N2 N 0.29999(10) 0.48296(10) 0.1104(3) 0.0641(9) Uani 1 1 d . . . N3 N 0.44501(8) 0.11940(8) 0.5808(2) 0.0381(6) Uani 1 1 d . . . N4 N 0.50519(10) 0.19688(9) 0.3991(3) 0.0615(8) Uani 1 1 d . . . N5 N 0.03692(9) 0.14035(9) 0.9203(2) 0.0474(7) Uani 1 1 d . . . N6 N -0.04445(10) 0.19901(11) 1.0965(3) 0.0680(9) Uani 1 1 d . . . N7 N 0.06190(9) 0.36616(9) 0.6147(2) 0.0490(7) Uani 1 1 d . B . N8 N -0.01104(11) 0.28789(10) 0.4630(3) 0.0674(9) Uani 1 1 d . . . O1 O 0.41931(7) 0.33806(6) 0.09843(16) 0.0402(5) Uani 1 1 d . . . O2 O 0.44901(12) 0.25471(8) 0.0844(2) 0.0857(10) Uani 1 1 d . . . O3 O 0.41711(9) 0.24498(8) -0.0816(2) 0.0664(7) Uani 1 1 d . . . O4 O 0.34450(8) 0.32029(9) -0.2016(2) 0.0671(7) Uani 1 1 d . . . O5 O 0.41549(9) 0.32408(9) -0.26413(19) 0.0643(7) Uani 1 1 d . . . O6 O 0.43510(6) 0.49322(7) 0.0236(2) 0.0458(5) Uani 1 1 d . . . H6A H 0.4472 0.4695 0.0043 0.069 Uiso 1 1 calc R . . O7 O 0.34986(7) 0.11063(8) 0.39885(18) 0.0509(6) Uani 1 1 d . . . O8 O 0.26141(8) 0.11195(13) 0.4010(2) 0.0972(11) Uani 1 1 d . . . O9 O 0.25830(8) 0.12498(12) 0.5819(2) 0.0866(9) Uani 1 1 d . . . O10 O 0.34188(9) 0.17399(8) 0.7136(2) 0.0634(7) Uani 1 1 d . . . O11 O 0.33969(8) 0.10135(8) 0.76347(19) 0.0593(7) Uani 1 1 d . . . O12 O 0.50388(7) 0.05957(7) 0.4657(2) 0.0490(6) Uani 1 1 d . . . H12 H 0.4792 0.0469 0.4686 0.073 Uiso 1 1 calc R . . O13 O 0.13254(7) 0.12592(8) 1.09876(19) 0.0515(6) Uani 1 1 d . . . O14 O 0.22029(9) 0.12414(13) 1.0937(2) 0.0966(11) Uani 1 1 d . . . O15 O 0.22351(9) 0.15720(12) 0.9290(3) 0.0989(11) Uani 1 1 d . . . O16 O 0.14420(19) 0.19512(18) 0.7905(4) 0.0858(14) Uani 0.659(3) 1 d PU A 1 O17 O 0.14329(15) 0.12368(16) 0.7360(3) 0.0675(10) Uani 0.659(3) 1 d PU A 1 O16' O 0.1547(4) 0.1541(4) 0.7520(9) 0.0858(14) Uani 0.341(3) 1 d PU A 2 O17' O 0.1183(3) 0.2135(3) 0.8164(7) 0.0675(10) Uani 0.341(3) 1 d PU A 2 O18 O -0.01141(7) 0.06545(7) 1.0148(2) 0.0625(7) Uani 1 1 d . . . H18A H 0.0149 0.0600 0.9975 0.094 Uiso 1 1 calc R . . O19 O 0.15377(7) 0.39419(8) 0.43397(18) 0.0480(6) Uani 1 1 d . . . O20 O 0.24099(8) 0.40532(13) 0.4350(2) 0.0922(11) Uani 1 1 d . . . O21 O 0.24774(8) 0.38298(11) 0.6103(2) 0.0771(8) Uani 1 1 d . . . O23 O 0.16878(11) 0.39584(11) 0.7942(2) 0.0922(10) Uani 1 1 d . B . O24 O -0.00116(7) 0.42822(7) 0.5115(2) 0.0527(6) Uani 1 1 d . . . H24A H 0.0227 0.4425 0.5113 0.079 Uiso 1 1 calc R B . 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 0.0792(2) 0.0598(2) 0.03231(17) -0.00045(16) -0.00524(17) 0.00651(18) Br2 0.0909(3) 0.0797(3) 0.04070(17) -0.00366(19) -0.0001(2) 0.0017(2) Br3 0.0806(3) 0.0788(3) 0.0477(2) 0.0111(2) 0.0036(2) 0.0034(2) Br4 0.0790(3) 0.1293(4) 0.04270(18) 0.0046(3) -0.0047(2) -0.0012(3) C1 0.0415(18) 0.046(2) 0.0335(17) 0.0052(15) -0.0046(14) -0.0019(15) C2 0.0374(17) 0.0361(17) 0.0386(18) -0.0021(14) -0.0010(14) -0.0032(14) C3 0.0282(15) 0.0292(16) 0.0392(17) -0.0044(13) 0.0036(13) -0.0025(13) C4 0.0288(16) 0.0318(17) 0.0414(17) -0.0032(14) 0.0022(13) 0.0014(13) C5 0.057(2) 0.0333(18) 0.051(2) -0.0072(16) 0.0027(17) 0.0018(16) C6 0.068(2) 0.046(2) 0.0386(19) -0.0143(16) 0.0018(17) -0.0013(18) C7 0.0344(16) 0.0241(16) 0.0391(17) 0.0027(13) 0.0005(13) -0.0017(13) C8 0.0568(19) 0.0296(15) 0.0387(19) -0.0045(14) -0.0020(16) -0.0031(14) C9 0.086(3) 0.0304(17) 0.050(2) -0.0032(17) 0.000(2) 0.0028(16) C10 0.276(8) 0.042(3) 0.091(4) -0.003(2) -0.037(4) 0.059(3) C11 0.0364(17) 0.0326(17) 0.0334(16) 0.0001(13) -0.0006(14) -0.0032(14) C12 0.056(2) 0.0351(18) 0.0422(19) -0.0027(15) -0.0044(17) 0.0005(16) C13 0.080(3) 0.126(4) 0.071(3) -0.004(3) -0.037(2) -0.035(3) C14 0.0278(14) 0.0351(16) 0.0335(16) -0.0016(14) -0.0003(13) -0.0002(12) C15 0.078(3) 0.046(2) 0.0332(17) 0.0019(15) -0.0086(17) 0.0208(19) C16 0.104(4) 0.135(4) 0.066(3) 0.003(3) -0.043(3) 0.049(3) C17 0.155(4) 0.050(2) 0.045(2) 0.0038(19) 0.027(3) 0.003(3) C18 0.0387(16) 0.0363(16) 0.0392(17) 0.0004(14) -0.0048(15) 0.0093(13) C19 0.0295(17) 0.056(2) 0.065(2) -0.0013(18) -0.0027(16) 0.0071(16) C20 0.057(2) 0.089(3) 0.165(5) -0.058(3) 0.028(3) -0.018(2) C21 0.061(3) 0.108(4) 0.261(8) -0.062(5) 0.049(4) -0.037(3) C22 0.060(3) 0.096(4) 0.182(6) -0.012(4) 0.045(3) -0.009(3) C23 0.055(3) 0.082(3) 0.105(4) -0.015(3) 0.020(2) 0.015(2) C24 0.0347(17) 0.0313(16) 0.0409(17) -0.0006(13) 0.0024(14) 0.0067(13) C25 0.059(2) 0.0392(19) 0.0419(19) -0.0012(15) -0.0002(16) 0.0061(17) C26 0.052(2) 0.0430(19) 0.0379(17) 0.0022(15) 0.0007(16) 0.0024(15) C27 0.0395(18) 0.0307(16) 0.0407(18) 0.0029(14) 0.0070(14) 0.0034(14) C28 0.0433(19) 0.0270(16) 0.0491(19) 0.0046(14) 0.0081(16) -0.0005(14) C29 0.055(2) 0.056(2) 0.058(2) 0.0043(18) 0.0151(19) 0.0072(18) C30 0.071(3) 0.061(2) 0.040(2) 0.0026(17) 0.0210(19) 0.016(2) C31 0.0269(17) 0.0476(19) 0.0442(18) 0.0038(15) 0.0031(15) -0.0012(14) C32 0.0391(18) 0.068(2) 0.046(2) 0.0010(18) 0.0039(17) 0.0036(16) C33 0.0379(19) 0.087(3) 0.065(3) -0.004(2) 0.000(2) 0.0067(18) C34 0.034(3) 0.266(8) 0.126(5) -0.024(5) -0.024(3) 0.003(3) C35 0.0434(19) 0.0388(18) 0.0442(19) 0.0046(15) 0.0041(16) 0.0013(15) C36 0.0380(18) 0.045(2) 0.0470(19) -0.0004(17) 0.0080(15) 0.0003(15) C37 0.104(3) 0.076(3) 0.074(3) -0.021(2) 0.026(3) 0.000(3) C38 0.0342(17) 0.0272(15) 0.0425(17) 0.0028(14) 0.0032(14) 0.0003(12) C39 0.044(2) 0.062(2) 0.0405(18) 0.0028(17) 0.0025(15) -0.0082(17) C40 0.095(3) 0.070(3) 0.063(3) -0.015(2) 0.003(2) -0.017(2) C41 0.057(2) 0.080(3) 0.051(2) 0.015(2) -0.0091(18) 0.002(2) C42 0.0378(16) 0.0346(16) 0.0513(19) 0.0042(16) -0.0015(16) -0.0028(13) C43 0.0470(18) 0.0325(16) 0.063(2) 0.0038(16) 0.0063(18) -0.0044(14) C44 0.094(3) 0.041(2) 0.111(4) 0.004(2) 0.053(3) -0.003(2) C45 0.118(4) 0.049(2) 0.160(5) 0.019(3) 0.076(4) 0.012(2) C46 0.106(4) 0.039(2) 0.143(4) 0.033(3) 0.046(3) 0.011(2) C47 0.091(3) 0.056(3) 0.097(3) 0.015(2) 0.036(3) -0.013(2) C48 0.0398(18) 0.0334(18) 0.057(2) 0.0048(15) 0.0079(16) 0.0004(14) C49 0.059(2) 0.0401(19) 0.053(2) 0.0050(16) 0.0094(18) 0.0010(17) C50 0.0441(19) 0.0386(18) 0.048(2) -0.0009(15) 0.0060(16) -0.0002(15) C51 0.0405(18) 0.0326(17) 0.0500(19) -0.0027(15) 0.0044(16) 0.0014(14) C52 0.0428(19) 0.0313(17) 0.060(2) -0.0055(16) 0.0125(17) -0.0002(15) C53 0.045(2) 0.065(2) 0.069(3) 0.003(2) 0.0141(19) -0.0090(19) C54 0.065(3) 0.066(3) 0.061(3) 0.013(2) 0.019(2) -0.013(2) C55 0.0373(19) 0.0418(19) 0.050(2) -0.0038(16) -0.0004(16) -0.0007(15) C56 0.0443(19) 0.066(2) 0.048(2) -0.0016(18) 0.0094(17) -0.0102(16) C57 0.042(2) 0.114(3) 0.054(3) 0.000(2) 0.000(2) -0.008(2) C58 0.035(3) 0.321(10) 0.109(4) 0.022(5) -0.009(3) -0.012(4) C59 0.047(2) 0.060(2) 0.044(2) -0.0003(17) 0.0026(17) -0.0122(17) C60 0.058(3) 0.049(4) 0.062(4) 0.003(3) -0.005(3) -0.011(3) C61 0.130(5) 0.112(6) 0.090(4) 0.028(5) 0.028(4) -0.020(5) C62 0.0376(18) 0.0420(18) 0.055(2) -0.0068(17) 0.0042(17) -0.0048(14) C63 0.056(2) 0.105(3) 0.051(2) -0.012(2) -0.0057(19) 0.005(2) C64 0.159(5) 0.158(5) 0.072(3) 0.031(3) -0.009(3) 0.058(4) C65 0.069(3) 0.196(5) 0.073(3) -0.065(3) 0.010(2) -0.031(3) C66 0.0356(16) 0.0522(18) 0.0494(19) -0.0094(16) -0.0025(16) 0.0049(14) C67 0.048(2) 0.0467(19) 0.052(2) -0.0048(16) 0.0001(17) 0.0114(16) C68 0.087(3) 0.046(2) 0.087(3) -0.003(2) 0.025(2) -0.0003(19) C69 0.106(3) 0.047(2) 0.117(4) -0.012(2) 0.021(3) -0.011(2) C70 0.105(4) 0.067(3) 0.113(4) -0.032(3) 0.002(3) 0.018(3) C71 0.072(3) 0.081(3) 0.103(4) -0.037(3) 0.009(3) 0.020(2) C72 0.0281(17) 0.0448(19) 0.066(2) -0.0078(17) 0.0026(16) -0.0008(15) C73 0.054(2) 0.055(2) 0.047(2) -0.0019(17) -0.0053(17) 0.0014(17) C74 0.0387(18) 0.049(2) 0.0473(18) 0.0020(15) -0.0012(15) 0.0015(15) C75 0.0323(16) 0.0290(16) 0.0465(18) 0.0015(14) -0.0053(14) 0.0041(13) C76 0.0360(17) 0.0309(17) 0.0537(18) -0.0043(14) -0.0093(15) 0.0051(14) C77 0.0345(18) 0.053(2) 0.064(2) -0.0059(17) -0.0111(16) 0.0064(16) C78 0.051(2) 0.074(3) 0.047(2) -0.0089(18) -0.0161(17) 0.0087(19) C79 0.0295(16) 0.0397(18) 0.0440(17) -0.0041(14) 0.0005(14) -0.0010(14) C80 0.0330(17) 0.074(2) 0.0456(19) -0.0011(18) -0.0099(16) 0.0031(16) C81 0.0404(19) 0.087(3) 0.056(2) 0.003(2) -0.0078(19) -0.0028(19) C82 0.041(3) 0.288(8) 0.090(4) 0.039(4) 0.003(2) -0.029(4) C83 0.0428(19) 0.051(2) 0.0418(18) -0.0038(15) -0.0094(15) 0.0072(16) C84 0.050(2) 0.071(3) 0.053(2) 0.006(2) -0.0047(18) 0.0080(19) C85 0.218(13) 0.158(9) 0.107(5) 0.056(5) -0.030(7) 0.044(8) O22 0.091(5) 0.077(2) 0.062(3) 0.0196(17) -0.017(3) 0.012(2) C85' 0.218(13) 0.158(9) 0.107(5) 0.056(5) -0.030(7) 0.044(8) O22' 0.091(5) 0.077(2) 0.062(3) 0.0196(17) -0.017(3) 0.012(2) C86 0.0345(17) 0.0369(18) 0.0490(18) -0.0035(15) -0.0016(15) 0.0022(14) C87 0.056(2) 0.094(3) 0.044(2) 0.000(2) 0.0036(18) -0.012(2) C88 0.189(6) 0.130(4) 0.065(3) 0.033(3) -0.006(4) -0.043(4) C89 0.060(3) 0.192(5) 0.061(3) -0.049(3) 0.010(2) 0.002(3) C90 0.0396(18) 0.0452(19) 0.050(2) -0.0072(15) 0.0033(15) -0.0080(15) C91 0.057(2) 0.0406(17) 0.054(2) 0.0062(17) 0.0043(18) -0.0037(16) C92 0.066(2) 0.049(2) 0.134(4) -0.007(3) -0.018(3) 0.0065(19) C93 0.101(3) 0.050(3) 0.190(6) -0.009(3) 0.000(4) 0.021(2) C94 0.119(4) 0.041(2) 0.145(5) -0.022(3) -0.007(4) 0.005(3) C95 0.098(3) 0.059(3) 0.109(4) -0.010(3) -0.024(3) -0.003(2) C96 0.0345(17) 0.0347(17) 0.061(2) -0.0073(15) -0.0016(15) -0.0001(13) C60' 0.058(3) 0.049(4) 0.062(4) 0.003(3) -0.005(3) -0.011(3) C61' 0.130(5) 0.112(6) 0.090(4) 0.028(5) 0.028(4) -0.020(5) N1 0.0428(15) 0.0389(15) 0.0347(14) 0.0027(12) -0.0037(12) 0.0097(12) N2 0.0449(18) 0.065(2) 0.082(2) -0.0086(18) 0.0202(17) 0.0081(16) N3 0.0366(15) 0.0357(14) 0.0419(15) 0.0078(12) 0.0035(12) -0.0108(12) N4 0.069(2) 0.0404(17) 0.075(2) 0.0163(15) 0.0255(17) -0.0052(15) N5 0.0375(16) 0.0575(18) 0.0472(17) -0.0040(14) 0.0017(13) 0.0010(13) N6 0.056(2) 0.066(2) 0.082(2) -0.0218(18) 0.0090(18) 0.0084(17) N7 0.0451(17) 0.0565(18) 0.0453(16) -0.0048(14) 0.0047(13) -0.0046(14) N8 0.068(2) 0.0510(18) 0.083(2) -0.0191(17) -0.0119(18) -0.0033(15) O1 0.0642(14) 0.0245(11) 0.0318(11) -0.0007(9) -0.0020(10) 0.0013(10) O2 0.171(3) 0.0363(14) 0.0494(16) 0.0047(12) -0.0219(18) 0.0269(16) O3 0.101(2) 0.0360(14) 0.0624(17) -0.0160(12) -0.0067(15) -0.0035(13) O4 0.0548(16) 0.0894(19) 0.0571(15) -0.0087(14) -0.0129(13) -0.0157(14) O5 0.0702(17) 0.0818(19) 0.0409(14) -0.0130(13) 0.0040(13) -0.0023(14) O6 0.0382(12) 0.0430(12) 0.0564(14) 0.0088(12) 0.0077(11) 0.0000(9) O7 0.0339(13) 0.0810(17) 0.0377(12) -0.0005(12) 0.0003(10) 0.0009(12) O8 0.0381(15) 0.185(3) 0.0688(19) -0.005(2) -0.0095(14) 0.0063(18) O9 0.0378(15) 0.149(3) 0.073(2) -0.0106(19) 0.0120(14) 0.0119(16) O10 0.0812(18) 0.0529(16) 0.0562(15) -0.0046(12) 0.0274(14) -0.0033(13) O11 0.0734(17) 0.0571(15) 0.0473(14) 0.0084(13) 0.0123(12) -0.0032(13) O12 0.0455(12) 0.0339(12) 0.0676(15) 0.0075(11) -0.0012(12) 0.0028(10) O13 0.0359(13) 0.0732(17) 0.0454(13) 0.0046(12) -0.0009(11) -0.0038(11) O14 0.0386(15) 0.183(3) 0.0678(19) 0.013(2) -0.0044(14) -0.0009(18) O15 0.0541(17) 0.157(3) 0.085(2) 0.029(2) 0.0156(16) -0.0294(19) O16 0.103(3) 0.078(3) 0.076(3) 0.006(2) 0.017(2) -0.005(3) O17 0.078(2) 0.066(2) 0.058(2) -0.0019(19) 0.0133(18) -0.002(2) O16' 0.103(3) 0.078(3) 0.076(3) 0.006(2) 0.017(2) -0.005(3) O17' 0.078(2) 0.066(2) 0.058(2) -0.0019(19) 0.0133(18) -0.002(2) O18 0.0492(13) 0.0526(14) 0.0858(19) -0.0157(14) -0.0018(15) -0.0019(11) O19 0.0263(12) 0.0735(16) 0.0443(13) 0.0055(11) -0.0027(10) -0.0017(11) O20 0.0332(14) 0.183(3) 0.0599(18) 0.0160(19) -0.0083(13) -0.0191(17) O21 0.0389(14) 0.120(2) 0.0719(18) 0.0091(17) -0.0248(14) -0.0003(15) O23 0.108(2) 0.108(2) 0.0605(17) -0.0232(18) -0.0281(17) 0.0063(19) O24 0.0385(12) 0.0413(12) 0.0784(17) -0.0130(13) 0.0119(13) -0.0022(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.898(3) . ? Br2 C25 1.910(3) . ? Br3 C49 1.891(4) . ? Br4 C73 1.909(3) . ? C1 C2 1.362(4) . ? C1 C6 1.377(4) . ? C2 C3 1.392(4) . ? C2 H2 0.9300 . ? C3 C4 1.414(4) . ? C3 C7 1.452(4) . ? C4 C5 1.394(4) . ? C4 C24 1.500(4) . ? C5 C6 1.371(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C14 1.385(4) . ? C7 O1 1.390(3) . ? C8 C11 1.328(4) . ? C8 O1 1.345(3) . ? C8 C9 1.486(4) . ? C9 O3 1.183(4) . ? C9 O2 1.324(4) . ? C10 O2 1.470(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C14 1.444(4) . ? C11 C12 1.486(4) . ? C12 O5 1.195(4) . ? C12 O4 1.331(4) . ? C13 O4 1.460(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N1 1.375(4) . ? C15 N1 1.469(4) . ? C15 C16 1.508(5) . ? C15 C17 1.523(5) . ? C15 H15 0.9800 . ? 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 N1 1.464(4) . ? C18 C19 1.514(4) . ? C18 C24 1.544(4) . ? C18 H18 0.9800 . ? C19 N2 1.314(4) . ? C19 C20 1.365(5) . ? C20 C21 1.394(6) . ? C20 H20 0.9300 . ? C21 C22 1.379(7) . ? C21 H21 0.9300 . ? C22 C23 1.345(6) . ? C22 H22 0.9300 . ? C23 N2 1.336(5) . ? C23 H23 0.9300 . ? C24 O6 1.418(3) . ? C24 H24 0.9800 . ? C25 C26 1.352(4) . ? C25 C30 1.364(5) . ? C26 C27 1.413(4) . ? C26 H26 0.9300 . ? C27 C28 1.385(4) . ? C27 C31 1.444(4) . ? C28 C29 1.417(5) . ? C28 C48 1.492(5) . ? C29 C30 1.359(5) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C38 1.377(4) . ? C31 O7 1.386(4) . ? C32 O7 1.352(4) . ? C32 C35 1.355(4) . ? C32 C33 1.464(4) . ? C33 O9 1.186(4) . ? C33 O8 1.328(5) . ? C34 O8 1.455(5) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C38 1.432(4) . ? C35 C36 1.501(4) . ? C36 O11 1.180(4) . ? C36 O10 1.329(4) . ? C37 O10 1.463(4) . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 N3 1.378(4) . ? C39 N3 1.480(4) . ? C39 C41 1.526(5) . ? C39 C40 1.529(5) . ? C39 H39 0.9800 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 N3 1.440(4) . ? C42 C43 1.523(4) . ? C42 C48 1.549(4) . ? C42 H42 0.9800 . ? C43 N4 1.326(4) . ? C43 C44 1.363(5) . ? C44 C45 1.369(5) . ? C44 H44 0.9300 . ? C45 C46 1.376(6) . ? C45 H45 0.9300 . ? C46 C47 1.370(6) . ? C46 H46 0.9300 . ? C47 N4 1.345(5) . ? C47 H47 0.9300 . ? C48 O12 1.434(3) . ? C48 H48 0.9800 . ? C49 C50 1.365(4) . ? C49 C54 1.392(5) . ? C50 C51 1.398(4) . ? C50 H50 0.9300 . ? C51 C52 1.387(4) . ? C51 C55 1.451(4) . ? C52 C53 1.402(5) . ? C52 C72 1.493(5) . ? C53 C54 1.382(5) . ? C53 H53 0.9300 . ? C54 H54 0.9300 . ? C55 C62 1.369(5) . ? C55 O13 1.379(4) . ? C56 O13 1.341(4) . ? C56 C59 1.354(5) . ? C56 C57 1.471(5) . ? C57 O15 1.182(4) . ? C57 O14 1.318(5) . ? C58 O14 1.463(5) . ? C58 H58A 0.9600 . ? C58 H58B 0.9600 . ? C58 H58C 0.9600 . ? C59 C60' 1.432(15) . ? C59 C62 1.434(4) . ? C59 C60 1.575(8) . ? C60 O17 1.135(8) . ? C60 O16 1.330(8) . ? C61 O16 1.508(9) . ? C61 H61A 0.9600 . ? C61 H61B 0.9600 . ? C61 H61C 0.9600 . ? C62 N5 1.378(4) . ? C63 N5 1.476(4) . ? C63 C64 1.511(6) . ? C63 C65 1.515(6) . ? C63 H63 0.9800 . ? C64 H64A 0.9600 . ? C64 H64B 0.9600 . ? C64 H64C 0.9600 . ? C65 H65A 0.9600 . ? C65 H65B 0.9600 . ? C65 H65C 0.9600 . ? C66 N5 1.448(4) . ? C66 C67 1.526(4) . ? C66 C72 1.549(5) . ? C66 H66 0.9800 . ? C67 N6 1.326(4) . ? C67 C68 1.359(5) . ? C68 C69 1.363(5) . ? C68 H68 0.9300 . ? C69 C70 1.350(6) . ? C69 H69 0.9300 . ? C70 C71 1.376(6) . ? C70 H70 0.9300 . ? C71 N6 1.345(5) . ? C71 H71 0.9300 . ? C72 O18 1.432(4) . ? C72 H72 0.9800 . ? C73 C78 1.363(5) . ? C73 C74 1.371(4) . ? C74 C75 1.401(4) . ? C74 H74 0.9300 . ? C75 C76 1.390(4) . ? C75 C79 1.443(4) . ? C76 C77 1.403(5) . ? C76 C96 1.500(5) . ? C77 C78 1.376(5) . ? C77 H77 0.9300 . ? C78 H78 0.9300 . ? C79 O19 1.383(3) . ? C79 C86 1.384(4) . ? C80 C83 1.346(5) . ? C80 O19 1.347(4) . ? C80 C81 1.464(5) . ? C81 O21 1.195(4) . ? C81 O20 1.317(5) . ? C82 O20 1.447(5) . ? C82 H82A 0.9600 . ? C82 H82B 0.9600 . ? C82 H82C 0.9600 . ? C83 C86 1.447(4) . ? C83 C84 1.493(5) . ? C84 O23 1.199(4) . ? C84 O22' 1.302(13) . ? C84 O22 1.309(6) . ? C85 O22 1.489(8) . ? C85 H85A 0.9600 . ? C85 H85B 0.9600 . ? C85 H85C 0.9600 . ? C85' O22' 1.508(16) . ? C85' H85D 0.9600 . ? C85' H85E 0.9600 . ? C85' H85F 0.9600 . ? C86 N7 1.374(4) . ? C87 N7 1.461(4) . ? C87 C88 1.516(6) . ? C87 C89 1.524(6) . ? C87 H87 0.9800 . ? C88 H88A 0.9600 . ? C88 H88B 0.9600 . ? C88 H88C 0.9600 . ? C89 H89A 0.9600 . ? C89 H89B 0.9600 . ? C89 H89C 0.9600 . ? C90 N7 1.441(4) . ? C90 C91 1.516(4) . ? C90 C96 1.547(4) . ? C90 H90 0.9800 . ? C91 N8 1.320(4) . ? C91 C92 1.362(5) . ? C92 C93 1.401(6) . ? C92 H92 0.9300 . ? C93 C94 1.330(7) . ? C93 H93 0.9300 . ? C94 C95 1.361(6) . ? C94 H94 0.9300 . ? C95 N8 1.342(5) . ? C95 H95 0.9300 . ? C96 O24 1.432(3) . ? C96 H96 0.9800 . ? C60' O17' 1.240(15) . ? C60' O16' 1.337(18) . ? C61' O16' 1.371(18) . ? C61' H61D 0.9600 . ? C61' H61E 0.9600 . ? C61' H61F 0.9600 . ? O6 H6A 0.8200 . ? O12 H12 0.8200 . ? O18 H18A 0.8200 . ? O24 H24A 0.8200 . ? 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 121.8(3) . . ? C2 C1 Br1 119.0(2) . . ? C6 C1 Br1 119.2(2) . . ? C1 C2 C3 120.8(3) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C2 C3 C4 119.1(3) . . ? C2 C3 C7 119.4(3) . . ? C4 C3 C7 121.5(3) . . ? C5 C4 C3 117.4(3) . . ? C5 C4 C24 119.0(3) . . ? C3 C4 C24 123.6(3) . . ? C6 C5 C4 123.3(3) . . ? C6 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? C5 C6 C1 117.7(3) . . ? C5 C6 H6 121.1 . . ? C1 C6 H6 121.1 . . ? C14 C7 O1 109.1(2) . . ? C14 C7 C3 137.1(3) . . ? O1 C7 C3 113.6(2) . . ? C11 C8 O1 112.5(2) . . ? C11 C8 C9 129.1(3) . . ? O1 C8 C9 118.5(3) . . ? O3 C9 O2 126.7(3) . . ? O3 C9 C8 122.3(3) . . ? O2 C9 C8 111.1(3) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 C14 106.6(3) . . ? C8 C11 C12 124.0(3) . . ? C14 C11 C12 129.3(3) . . ? O5 C12 O4 124.0(3) . . ? O5 C12 C11 125.3(3) . . ? O4 C12 C11 110.7(3) . . ? O4 C13 H13A 109.5 . . ? O4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 C7 127.4(3) . . ? N1 C14 C11 127.3(3) . . ? C7 C14 C11 105.3(2) . . ? N1 C15 C16 111.1(3) . . ? N1 C15 C17 112.7(3) . . ? C16 C15 C17 112.6(3) . . ? N1 C15 H15 106.7 . . ? C16 C15 H15 106.7 . . ? C17 C15 H15 106.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C18 C19 113.7(2) . . ? N1 C18 C24 114.2(2) . . ? C19 C18 C24 111.3(3) . . ? N1 C18 H18 105.5 . . ? C19 C18 H18 105.5 . . ? C24 C18 H18 105.5 . . ? N2 C19 C20 122.7(3) . . ? N2 C19 C18 112.9(3) . . ? C20 C19 C18 124.3(3) . . ? C19 C20 C21 118.3(4) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? C22 C21 C20 119.1(5) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C23 C22 C21 117.4(5) . . ? C23 C22 H22 121.3 . . ? C21 C22 H22 121.3 . . ? N2 C23 C22 124.5(4) . . ? N2 C23 H23 117.7 . . ? C22 C23 H23 117.7 . . ? O6 C24 C4 112.3(2) . . ? O6 C24 C18 111.4(2) . . ? C4 C24 C18 115.0(2) . . ? O6 C24 H24 105.8 . . ? C4 C24 H24 105.8 . . ? C18 C24 H24 105.8 . . ? C26 C25 C30 121.9(3) . . ? C26 C25 Br2 118.3(3) . . ? C30 C25 Br2 119.7(3) . . ? C25 C26 C27 120.7(3) . . ? C25 C26 H26 119.7 . . ? C27 C26 H26 119.7 . . ? C28 C27 C26 118.4(3) . . ? C28 C27 C31 123.2(3) . . ? C26 C27 C31 118.4(3) . . ? C27 C28 C29 118.4(3) . . ? C27 C28 C48 124.3(3) . . ? C29 C28 C48 117.2(3) . . ? C30 C29 C28 121.9(3) . . ? C30 C29 H29 119.0 . . ? C28 C29 H29 119.0 . . ? C29 C30 C25 118.6(3) . . ? C29 C30 H30 120.7 . . ? C25 C30 H30 120.7 . . ? C38 C31 O7 109.0(3) . . ? C38 C31 C27 137.8(3) . . ? O7 C31 C27 113.2(3) . . ? O7 C32 C35 110.9(3) . . ? O7 C32 C33 119.2(3) . . ? C35 C32 C33 129.9(3) . . ? O9 C33 O8 125.0(3) . . ? O9 C33 C32 123.5(4) . . ? O8 C33 C32 111.5(3) . . ? O8 C34 H34A 109.5 . . ? O8 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O8 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 C38 106.6(3) . . ? C32 C35 C36 122.9(3) . . ? C38 C35 C36 130.5(3) . . ? O11 C36 O10 125.2(3) . . ? O11 C36 C35 125.1(3) . . ? O10 C36 C35 109.7(3) . . ? O10 C37 H37A 109.5 . . ? O10 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O10 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C31 C38 N3 125.7(3) . . ? C31 C38 C35 106.3(3) . . ? N3 C38 C35 128.0(3) . . ? N3 C39 C41 112.2(3) . . ? N3 C39 C40 112.2(3) . . ? C41 C39 C40 111.6(3) . . ? N3 C39 H39 106.8 . . ? C41 C39 H39 106.8 . . ? C40 C39 H39 106.8 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? N3 C42 C43 113.2(2) . . ? N3 C42 C48 114.7(2) . . ? C43 C42 C48 111.3(3) . . ? N3 C42 H42 105.6 . . ? C43 C42 H42 105.6 . . ? C48 C42 H42 105.6 . . ? N4 C43 C44 122.6(3) . . ? N4 C43 C42 114.7(3) . . ? C44 C43 C42 122.5(3) . . ? C43 C44 C45 120.2(4) . . ? C43 C44 H44 119.9 . . ? C45 C44 H44 119.9 . . ? C44 C45 C46 118.2(4) . . ? C44 C45 H45 120.9 . . ? C46 C45 H45 120.9 . . ? C47 C46 C45 118.3(4) . . ? C47 C46 H46 120.9 . . ? C45 C46 H46 120.9 . . ? N4 C47 C46 123.5(4) . . ? N4 C47 H47 118.2 . . ? C46 C47 H47 118.2 . . ? O12 C48 C28 110.7(2) . . ? O12 C48 C42 108.3(2) . . ? C28 C48 C42 117.8(3) . . ? O12 C48 H48 106.5 . . ? C28 C48 H48 106.5 . . ? C42 C48 H48 106.5 . . ? C50 C49 C54 120.6(3) . . ? C50 C49 Br3 119.5(3) . . ? C54 C49 Br3 119.9(3) . . ? C49 C50 C51 121.2(3) . . ? C49 C50 H50 119.4 . . ? C51 C50 H50 119.4 . . ? C52 C51 C50 119.3(3) . . ? C52 C51 C55 122.7(3) . . ? C50 C51 C55 118.0(3) . . ? C51 C52 C53 118.6(3) . . ? C51 C52 C72 123.5(3) . . ? C53 C52 C72 117.9(3) . . ? C54 C53 C52 121.9(3) . . ? C54 C53 H53 119.1 . . ? C52 C53 H53 119.1 . . ? C53 C54 C49 118.4(3) . . ? C53 C54 H54 120.8 . . ? C49 C54 H54 120.8 . . ? C62 C55 O13 109.4(3) . . ? C62 C55 C51 137.0(3) . . ? O13 C55 C51 113.6(3) . . ? O13 C56 C59 110.4(3) . . ? O13 C56 C57 118.7(3) . . ? C59 C56 C57 130.9(3) . . ? O15 C57 O14 125.8(3) . . ? O15 C57 C56 123.5(4) . . ? O14 C57 C56 110.6(3) . . ? O14 C58 H58A 109.5 . . ? O14 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? O14 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C56 C59 C60' 122.6(6) . . ? C56 C59 C62 107.0(3) . . ? C60' C59 C62 125.2(6) . . ? C56 C59 C60 119.0(3) . . ? C60' C59 C60 30.9(5) . . ? C62 C59 C60 132.7(4) . . ? O17 C60 O16 127.1(7) . . ? O17 C60 C59 128.9(6) . . ? O16 C60 C59 103.9(6) . . ? C55 C62 N5 127.4(3) . . ? C55 C62 C59 105.6(3) . . ? N5 C62 C59 126.9(3) . . ? N5 C63 C64 111.7(4) . . ? N5 C63 C65 111.5(4) . . ? C64 C63 C65 113.4(4) . . ? N5 C63 H63 106.6 . . ? C64 C63 H63 106.6 . . ? C65 C63 H63 106.6 . . ? C63 C64 H64A 109.5 . . ? C63 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? C63 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? C63 C65 H65A 109.5 . . ? C63 C65 H65B 109.5 . . ? H65A C65 H65B 109.5 . . ? C63 C65 H65C 109.5 . . ? H65A C65 H65C 109.5 . . ? H65B C65 H65C 109.5 . . ? N5 C66 C67 113.4(3) . . ? N5 C66 C72 114.6(2) . . ? C67 C66 C72 110.9(3) . . ? N5 C66 H66 105.7 . . ? C67 C66 H66 105.7 . . ? C72 C66 H66 105.7 . . ? N6 C67 C68 122.6(3) . . ? N6 C67 C66 112.7(3) . . ? C68 C67 C66 124.6(3) . . ? C67 C68 C69 118.6(4) . . ? C67 C68 H68 120.7 . . ? C69 C68 H68 120.7 . . ? C70 C69 C68 120.2(4) . . ? C70 C69 H69 119.9 . . ? C68 C69 H69 119.9 . . ? C69 C70 C71 118.7(4) . . ? C69 C70 H70 120.6 . . ? C71 C70 H70 120.6 . . ? N6 C71 C70 121.4(4) . . ? N6 C71 H71 119.3 . . ? C70 C71 H71 119.3 . . ? O18 C72 C52 112.0(3) . . ? O18 C72 C66 109.6(3) . . ? C52 C72 C66 117.1(3) . . ? O18 C72 H72 105.8 . . ? C52 C72 H72 105.8 . . ? C66 C72 H72 105.8 . . ? C78 C73 C74 122.3(3) . . ? C78 C73 Br4 119.5(3) . . ? C74 C73 Br4 118.2(3) . . ? C73 C74 C75 120.0(3) . . ? C73 C74 H74 120.0 . . ? C75 C74 H74 120.0 . . ? C76 C75 C74 119.3(3) . . ? C76 C75 C79 123.2(3) . . ? C74 C75 C79 117.5(3) . . ? C75 C76 C77 118.1(3) . . ? C75 C76 C96 123.7(3) . . ? C77 C76 C96 118.1(3) . . ? C78 C77 C76 122.5(3) . . ? C78 C77 H77 118.7 . . ? C76 C77 H77 118.7 . . ? C73 C78 C77 117.7(3) . . ? C73 C78 H78 121.1 . . ? C77 C78 H78 121.1 . . ? O19 C79 C86 109.0(3) . . ? O19 C79 C75 113.9(3) . . ? C86 C79 C75 137.0(3) . . ? C83 C80 O19 111.3(3) . . ? C83 C80 C81 129.8(3) . . ? O19 C80 C81 118.8(3) . . ? O21 C81 O20 125.8(3) . . ? O21 C81 C80 122.9(4) . . ? O20 C81 C80 111.3(3) . . ? O20 C82 H82A 109.5 . . ? O20 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? O20 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? C80 C83 C86 106.6(3) . . ? C80 C83 C84 122.0(3) . . ? C86 C83 C84 131.4(3) . . ? O23 C84 O22' 121.7(10) . . ? O23 C84 O22 125.0(5) . . ? O22' C84 O22 21.8(11) . . ? O23 C84 C83 123.4(4) . . ? O22' C84 C83 113.0(10) . . ? O22 C84 C83 111.1(4) . . ? C84 O22 C85 112.0(8) . . ? O22' C85' H85D 109.5 . . ? O22' C85' H85E 109.5 . . ? H85D C85' H85E 109.5 . . ? O22' C85' H85F 109.5 . . ? H85D C85' H85F 109.5 . . ? H85E C85' H85F 109.5 . . ? C84 O22' C85' 127(2) . . ? N7 C86 C79 126.5(3) . . ? N7 C86 C83 127.9(3) . . ? C79 C86 C83 105.6(3) . . ? N7 C87 C88 111.3(4) . . ? N7 C87 C89 111.9(3) . . ? C88 C87 C89 112.2(4) . . ? N7 C87 H87 107.0 . . ? C88 C87 H87 107.0 . . ? C89 C87 H87 107.0 . . ? C87 C88 H88A 109.5 . . ? C87 C88 H88B 109.5 . . ? H88A C88 H88B 109.5 . . ? C87 C88 H88C 109.5 . . ? H88A C88 H88C 109.5 . . ? H88B C88 H88C 109.5 . . ? C87 C89 H89A 109.5 . . ? C87 C89 H89B 109.5 . . ? H89A C89 H89B 109.5 . . ? C87 C89 H89C 109.5 . . ? H89A C89 H89C 109.5 . . ? H89B C89 H89C 109.5 . . ? N7 C90 C91 115.5(3) . . ? N7 C90 C96 115.5(3) . . ? C91 C90 C96 109.8(3) . . ? N7 C90 H90 104.9 . . ? C91 C90 H90 104.9 . . ? C96 C90 H90 104.9 . . ? N8 C91 C92 121.5(3) . . ? N8 C91 C90 113.9(3) . . ? C92 C91 C90 124.7(3) . . ? C91 C92 C93 118.7(4) . . ? C91 C92 H92 120.6 . . ? C93 C92 H92 120.6 . . ? C94 C93 C92 119.4(4) . . ? C94 C93 H93 120.3 . . ? C92 C93 H93 120.3 . . ? C93 C94 C95 119.0(4) . . ? C93 C94 H94 120.5 . . ? C95 C94 H94 120.5 . . ? N8 C95 C94 122.5(4) . . ? N8 C95 H95 118.8 . . ? C94 C95 H95 118.8 . . ? O24 C96 C76 112.5(3) . . ? O24 C96 C90 109.9(3) . . ? C76 C96 C90 116.1(2) . . ? O24 C96 H96 105.9 . . ? C76 C96 H96 105.9 . . ? C90 C96 H96 105.9 . . ? O17' C60' O16' 117.3(13) . . ? O17' C60' C59 129.0(12) . . ? O16' C60' C59 113.7(11) . . ? O16' C61' H61D 109.5 . . ? O16' C61' H61E 109.5 . . ? H61D C61' H61E 109.5 . . ? O16' C61' H61F 109.5 . . ? H61D C61' H61F 109.5 . . ? H61E C61' H61F 109.5 . . ? C14 N1 C18 119.6(2) . . ? C14 N1 C15 121.2(2) . . ? C18 N1 C15 119.1(2) . . ? C19 N2 C23 117.8(3) . . ? C38 N3 C42 118.8(2) . . ? C38 N3 C39 121.6(2) . . ? C42 N3 C39 119.6(2) . . ? C43 N4 C47 117.1(3) . . ? C62 N5 C66 120.1(3) . . ? C62 N5 C63 121.8(3) . . ? C66 N5 C63 118.0(3) . . ? C67 N6 C71 118.4(3) . . ? C86 N7 C90 120.9(3) . . ? C86 N7 C87 120.6(3) . . ? C90 N7 C87 118.4(3) . . ? C91 N8 C95 118.9(3) . . ? C8 O1 C7 106.5(2) . . ? C9 O2 C10 115.7(3) . . ? C12 O4 C13 116.8(3) . . ? C24 O6 H6A 109.5 . . ? C32 O7 C31 107.2(2) . . ? C33 O8 C34 114.6(3) . . ? C36 O10 C37 114.9(3) . . ? C48 O12 H12 109.5 . . ? C56 O13 C55 107.7(3) . . ? C57 O14 C58 115.2(4) . . ? C60 O16 C61 109.7(6) . . ? C60' O16' C61' 125.3(14) . . ? C72 O18 H18A 109.5 . . ? C80 O19 C79 107.6(2) . . ? C81 O20 C82 115.2(3) . . ? C96 O24 H24A 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.64 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.506 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.052 # Attachment '7m.cif' #1.Name of contact person #Ying Cheng #2.E-mail address of contact person #ycheng2@bnu.edu.cn #3.Authors'names #Huan-Rui Pan, Xiao-Rong Wang, Ying Cheng #4.Name of the journal to which the paper will be submitted #Org. Biomol. Chem. #5. Compound name #(5S,6S)-Dimethyl 8-bromo-6-hydroxyl-4-isopropyl-5- #(2-pyridyl)-5,6-dihydrobenzo[d]furo[3,2-b]azepine-2,3-dicarboxylate #6. Compound synonym #7. Formula C24 H23 Br N2 O6 #8. Formula weight 515.35 #9. Colour Colourless #10. Melting point 161-162 oC #11.Crystallization solvent Dichloromethane and n-butane data_101125c_0m _database_code_depnum_ccdc_archive 'CCDC 802476' #TrackingRef '7m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5S,6S)-Dimethyl 8-bromo-6-hydroxyl-4-isopropyl-5- (2-pyridyl)-5,6-dihydrobenzo[d]furo[3,2-b]azepine-2,3-dicarboxylate ; _chemical_name_common ; 5S,6S)-Dimethyl 8-bromo-6-hydroxyl-4-isopropyl-5-(2-pyridyl)- 5,6-dihydrobenzo(d)furo(3,2-b)azepine-2,3-dicarboxylate ; _chemical_melting_point ? _chemical_formula_moiety 'C24 H23 Br N2 O6' _chemical_formula_sum 'C24 H23 Br N2 O6' _chemical_formula_weight 515.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9953(17) _cell_length_b 12.083(3) _cell_length_c 13.275(3) _cell_angle_alpha 65.855(3) _cell_angle_beta 88.718(4) _cell_angle_gamma 84.251(4) _cell_volume 1164.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2300 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.01 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 1.808 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4837 _exptl_absorpt_correction_T_max 0.7732 _exptl_absorpt_process_details SADABS _exptl_special_details ; Melting point 161-162 oC Crystallization solvent Dichloromethane and n-butane ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 5905 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.25 _reflns_number_total 4184 _reflns_number_gt 3252 _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^)+(0.0343P)^2^+0.5980P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4184 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 0.90982(5) 0.82873(3) 0.67517(2) 0.07314(14) Uani 1 1 d . . . C1 C 0.8909(3) 0.7509(2) 0.5781(2) 0.0443(6) Uani 1 1 d . . . C2 C 0.8055(3) 0.6486(2) 0.6101(2) 0.0470(6) Uani 1 1 d . . . H2 H 0.7600 0.6156 0.6800 0.056 Uiso 1 1 calc R . . C3 C 0.7888(3) 0.5963(2) 0.53678(19) 0.0432(6) Uani 1 1 d . . . H3 H 0.7295 0.5282 0.5573 0.052 Uiso 1 1 calc R . . C4 C 0.8598(3) 0.6438(2) 0.43121(18) 0.0345(5) Uani 1 1 d . . . C5 C 0.9514(3) 0.7452(2) 0.40244(18) 0.0350(5) Uani 1 1 d . . . C6 C 0.9633(3) 0.7986(2) 0.47671(19) 0.0411(6) Uani 1 1 d . . . H6 H 1.0209 0.8673 0.4574 0.049 Uiso 1 1 calc R . . C7 C 1.0437(3) 0.7956(2) 0.29421(19) 0.0397(5) Uani 1 1 d . . . H7 H 1.1372 0.7349 0.2982 0.048 Uiso 1 1 calc R . . C8 C 0.9354(3) 0.81979(19) 0.19016(18) 0.0341(5) Uani 1 1 d . . . H8 H 0.9963 0.8750 0.1279 0.041 Uiso 1 1 calc R . . C9 C 0.7677(3) 0.89116(19) 0.18943(18) 0.0364(5) Uani 1 1 d . . . C10 C 0.6179(3) 0.8700(2) 0.1553(2) 0.0531(7) Uani 1 1 d . . . H10 H 0.6134 0.8074 0.1320 0.064 Uiso 1 1 calc R . . C11 C 0.4743(4) 0.9431(3) 0.1561(3) 0.0727(9) Uani 1 1 d . . . H11 H 0.3714 0.9303 0.1336 0.087 Uiso 1 1 calc R . . C12 C 0.4849(4) 1.0345(3) 0.1902(3) 0.0703(9) Uani 1 1 d . . . H12 H 0.3891 1.0839 0.1924 0.084 Uiso 1 1 calc R . . C13 C 0.6378(4) 1.0521(2) 0.2211(2) 0.0625(8) Uani 1 1 d . . . H13 H 0.6445 1.1157 0.2427 0.075 Uiso 1 1 calc R . . C14 C 1.0313(3) 0.7003(2) 0.0807(2) 0.0448(6) Uani 1 1 d . . . H14 H 1.0105 0.6233 0.0774 0.054 Uiso 1 1 calc R . . C15 C 1.2174(4) 0.6906(3) 0.1086(3) 0.0758(10) Uani 1 1 d . . . H15A H 1.2433 0.7650 0.1118 0.114 Uiso 1 1 calc R . . H15B H 1.2833 0.6768 0.0527 0.114 Uiso 1 1 calc R . . H15C H 1.2430 0.6239 0.1788 0.114 Uiso 1 1 calc R . . C16 C 0.9838(5) 0.8004(3) -0.0316(2) 0.0748(10) Uani 1 1 d . . . H16A H 0.8650 0.8059 -0.0444 0.112 Uiso 1 1 calc R . . H16B H 1.0432 0.7823 -0.0876 0.112 Uiso 1 1 calc R . . H16C H 1.0132 0.8767 -0.0343 0.112 Uiso 1 1 calc R . . C17 C 0.8550(3) 0.61384(19) 0.24587(17) 0.0319(5) Uani 1 1 d . . . C18 C 0.7863(3) 0.51896(19) 0.22552(18) 0.0343(5) Uani 1 1 d . . . C19 C 0.7708(3) 0.5090(2) 0.1176(2) 0.0412(6) Uani 1 1 d . . . C20 C 0.6577(5) 0.6093(3) -0.0631(2) 0.0757(10) Uani 1 1 d . . . H20A H 0.7638 0.6256 -0.0988 0.114 Uiso 1 1 calc R . . H20B H 0.5731 0.6734 -0.1043 0.114 Uiso 1 1 calc R . . H20C H 0.6271 0.5330 -0.0598 0.114 Uiso 1 1 calc R . . C21 C 0.7304(3) 0.4410(2) 0.32340(19) 0.0375(5) Uani 1 1 d . . . C22 C 0.6472(3) 0.3290(2) 0.3528(2) 0.0435(6) Uani 1 1 d . . . C23 C 0.5716(5) 0.1517(3) 0.5014(3) 0.0820(11) Uani 1 1 d . . . H23A H 0.4571 0.1639 0.4758 0.123 Uiso 1 1 calc R . . H23B H 0.5754 0.1156 0.5807 0.123 Uiso 1 1 calc R . . H23C H 0.6362 0.0987 0.4743 0.123 Uiso 1 1 calc R . . C24 C 0.8331(3) 0.58615(19) 0.35665(18) 0.0336(5) Uani 1 1 d . . . N1 N 0.7793(3) 0.98170(18) 0.22174(17) 0.0482(5) Uani 1 1 d . . . N2 N 0.9199(2) 0.71477(16) 0.16575(15) 0.0347(4) Uani 1 1 d . . . O1 O 1.1140(3) 0.9049(2) 0.27860(17) 0.0571(5) Uani 1 1 d . . . H1 H 1.033(4) 0.951(3) 0.267(3) 0.081(14) Uiso 1 1 d . . . O2 O 0.8389(3) 0.42972(18) 0.09556(16) 0.0704(6) Uani 1 1 d . . . O3 O 0.6713(2) 0.60295(16) 0.04818(14) 0.0527(5) Uani 1 1 d . . . O4 O 0.5932(3) 0.29864(17) 0.28551(16) 0.0637(5) Uani 1 1 d . . . O5 O 0.6411(2) 0.26808(16) 0.46143(15) 0.0582(5) Uani 1 1 d . . . O6 O 0.7553(2) 0.47987(13) 0.40388(12) 0.0390(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1105(3) 0.0783(2) 0.05270(19) -0.04670(17) 0.00687(16) -0.02127(19) C1 0.0539(15) 0.0484(15) 0.0372(13) -0.0255(12) -0.0057(11) 0.0018(12) C2 0.0630(17) 0.0474(15) 0.0312(12) -0.0173(11) 0.0041(11) -0.0035(13) C3 0.0550(15) 0.0377(13) 0.0366(13) -0.0146(11) 0.0040(11) -0.0070(11) C4 0.0382(13) 0.0332(12) 0.0326(12) -0.0148(10) 0.0002(10) 0.0001(10) C5 0.0339(12) 0.0383(13) 0.0361(12) -0.0189(10) -0.0014(9) -0.0018(10) C6 0.0441(14) 0.0434(14) 0.0418(13) -0.0233(11) -0.0025(11) -0.0051(11) C7 0.0389(13) 0.0422(14) 0.0470(14) -0.0262(12) 0.0086(11) -0.0110(11) C8 0.0427(13) 0.0293(12) 0.0343(12) -0.0160(10) 0.0107(10) -0.0106(10) C9 0.0479(14) 0.0273(12) 0.0329(12) -0.0108(10) 0.0102(10) -0.0070(10) C10 0.0513(17) 0.0433(15) 0.0684(18) -0.0267(14) 0.0029(14) -0.0045(13) C11 0.0506(18) 0.061(2) 0.104(3) -0.0324(19) 0.0030(17) -0.0013(15) C12 0.062(2) 0.0556(19) 0.083(2) -0.0218(17) 0.0180(17) 0.0113(16) C13 0.088(2) 0.0375(15) 0.0646(19) -0.0263(14) 0.0150(16) 0.0047(15) C14 0.0576(16) 0.0421(14) 0.0454(14) -0.0275(12) 0.0204(12) -0.0142(12) C15 0.059(2) 0.092(2) 0.109(3) -0.073(2) 0.0336(18) -0.0178(17) C16 0.125(3) 0.0579(19) 0.0424(16) -0.0204(14) 0.0275(17) -0.0206(19) C17 0.0369(12) 0.0269(11) 0.0322(11) -0.0128(9) 0.0036(9) -0.0016(9) C18 0.0425(13) 0.0280(11) 0.0344(12) -0.0150(10) -0.0002(10) -0.0021(10) C19 0.0530(15) 0.0358(13) 0.0406(13) -0.0201(11) 0.0052(11) -0.0115(12) C20 0.121(3) 0.070(2) 0.0397(16) -0.0226(15) -0.0115(17) -0.019(2) C21 0.0476(14) 0.0309(12) 0.0368(12) -0.0163(10) -0.0019(10) -0.0054(10) C22 0.0490(15) 0.0320(13) 0.0474(15) -0.0134(12) -0.0006(11) -0.0068(11) C23 0.090(2) 0.0461(18) 0.084(2) 0.0067(16) -0.0111(19) -0.0328(17) C24 0.0391(13) 0.0272(11) 0.0346(12) -0.0122(10) 0.0033(10) -0.0063(10) N1 0.0645(14) 0.0344(11) 0.0506(13) -0.0227(10) 0.0089(10) -0.0045(10) N2 0.0474(11) 0.0271(10) 0.0341(10) -0.0164(8) 0.0109(8) -0.0085(8) O1 0.0590(14) 0.0662(14) 0.0640(13) -0.0390(11) 0.0182(10) -0.0355(12) O2 0.1084(17) 0.0553(12) 0.0595(12) -0.0400(11) -0.0035(11) 0.0127(12) O3 0.0737(12) 0.0458(10) 0.0391(9) -0.0189(8) -0.0108(9) 0.0009(9) O4 0.0898(15) 0.0497(11) 0.0619(12) -0.0289(10) -0.0043(11) -0.0246(10) O5 0.0702(13) 0.0442(11) 0.0499(11) -0.0041(9) -0.0035(9) -0.0258(9) O6 0.0524(10) 0.0321(8) 0.0329(8) -0.0121(7) 0.0041(7) -0.0116(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.897(2) . ? C1 C6 1.370(3) . ? C1 C2 1.378(4) . ? C2 C3 1.375(3) . ? C2 H2 0.9300 . ? C3 C4 1.410(3) . ? C3 H3 0.9300 . ? C4 C5 1.403(3) . ? C4 C24 1.453(3) . ? C5 C6 1.391(3) . ? C5 C7 1.518(3) . ? C6 H6 0.9300 . ? C7 O1 1.423(3) . ? C7 C8 1.554(3) . ? C7 H7 0.9800 . ? C8 N2 1.449(3) . ? C8 C9 1.518(3) . ? C8 H8 0.9800 . ? C9 N1 1.340(3) . ? C9 C10 1.373(4) . ? C10 C11 1.380(4) . ? C10 H10 0.9300 . ? C11 C12 1.364(5) . ? C11 H11 0.9300 . ? C12 C13 1.361(5) . ? C12 H12 0.9300 . ? C13 N1 1.344(4) . ? C13 H13 0.9300 . ? C14 N2 1.478(3) . ? C14 C16 1.513(4) . ? C14 C15 1.523(4) . ? C14 H14 0.9800 . ? 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 C24 1.380(3) . ? C17 N2 1.389(3) . ? C17 C18 1.440(3) . ? C18 C21 1.354(3) . ? C18 C19 1.495(3) . ? C19 O2 1.190(3) . ? C19 O3 1.329(3) . ? C20 O3 1.454(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O6 1.357(3) . ? C21 C22 1.470(3) . ? C22 O4 1.198(3) . ? C22 O5 1.327(3) . ? C23 O5 1.449(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 O6 1.383(3) . ? O1 H1 0.79(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 C6 C1 C2 121.4(2) . . ? C6 C1 Br1 118.60(19) . . ? C2 C1 Br1 120.04(18) . . ? C3 C2 C1 118.9(2) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 121.3(2) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 118.6(2) . . ? C5 C4 C24 123.0(2) . . ? C3 C4 C24 118.5(2) . . ? C6 C5 C4 119.2(2) . . ? C6 C5 C7 118.9(2) . . ? C4 C5 C7 121.90(19) . . ? C1 C6 C5 120.6(2) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? O1 C7 C5 111.73(18) . . ? O1 C7 C8 108.4(2) . . ? C5 C7 C8 114.59(18) . . ? O1 C7 H7 107.3 . . ? C5 C7 H7 107.3 . . ? C8 C7 H7 107.3 . . ? N2 C8 C9 113.15(18) . . ? N2 C8 C7 115.76(18) . . ? C9 C8 C7 111.51(18) . . ? N2 C8 H8 105.1 . . ? C9 C8 H8 105.1 . . ? C7 C8 H8 105.1 . . ? N1 C9 C10 122.2(2) . . ? N1 C9 C8 113.5(2) . . ? C10 C9 C8 124.3(2) . . ? C9 C10 C11 118.8(3) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C12 C11 C10 119.3(3) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C13 C12 C11 119.0(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? N1 C13 C12 122.9(3) . . ? N1 C13 H13 118.5 . . ? C12 C13 H13 118.5 . . ? N2 C14 C16 110.3(2) . . ? N2 C14 C15 113.2(2) . . ? C16 C14 C15 112.2(3) . . ? N2 C14 H14 106.9 . . ? C16 C14 H14 106.9 . . ? C15 C14 H14 106.9 . . ? 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 . . ? C24 C17 N2 128.84(19) . . ? C24 C17 C18 106.03(18) . . ? N2 C17 C18 125.04(19) . . ? C21 C18 C17 106.67(19) . . ? C21 C18 C19 125.5(2) . . ? C17 C18 C19 127.72(19) . . ? O2 C19 O3 124.4(2) . . ? O2 C19 C18 125.4(2) . . ? O3 C19 C18 110.18(19) . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 O6 110.70(19) . . ? C18 C21 C22 131.1(2) . . ? O6 C21 C22 118.1(2) . . ? O4 C22 O5 125.5(2) . . ? O4 C22 C21 123.2(2) . . ? O5 C22 C21 111.3(2) . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C17 C24 O6 109.05(18) . . ? C17 C24 C4 136.4(2) . . ? O6 C24 C4 114.36(18) . . ? C9 N1 C13 117.8(2) . . ? C17 N2 C8 118.44(17) . . ? C17 N2 C14 120.06(17) . . ? C8 N2 C14 117.00(17) . . ? C7 O1 H1 101(3) . . ? C19 O3 C20 115.4(2) . . ? C22 O5 C23 116.9(2) . . ? C21 O6 C24 107.54(16) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.295 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.047