# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email xiaohua@sioc.ac.cn _publ_author_name 'Gang Zhao' data_cd201394 _database_code_depnum_ccdc_archive 'CCDC 860051' #TrackingRef 'cd201394.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 Br N O6' _chemical_formula_weight 478.33 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.1070(11) _cell_length_b 12.1050(16) _cell_length_c 11.6138(16) _cell_angle_alpha 90.00 _cell_angle_beta 101.055(2) _cell_angle_gamma 90.00 _cell_volume 1118.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2144 _cell_measurement_theta_min 4.909 _cell_measurement_theta_max 44.472 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.357 _exptl_crystal_size_mid 0.128 _exptl_crystal_size_min 0.124 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 1.874 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0946 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6158 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.0735 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4065 _reflns_number_gt 2675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0774P)^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 SHELXL _refine_ls_extinction_coef 0.014(3) _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 0.017(13) _chemical_absolute_configuration ad _refine_ls_number_reflns 4065 _refine_ls_number_parameters 285 _refine_ls_number_restraints 29 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1386 _refine_ls_wR_factor_gt 0.1301 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.949 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.002 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 -0.02566(9) 0.50074(6) 1.29440(5) 0.0874(3) Uani 1 1 d . . . N1 N 0.1609(7) 0.9379(4) 1.0208(4) 0.0729(13) Uani 1 1 d . . . O1 O 0.4193(6) 0.7307(4) 1.1341(6) 0.1096(18) Uani 1 1 d . . . O2 O 0.2774(5) 0.5739(3) 1.1409(4) 0.0747(11) Uani 1 1 d . . . O3 O 0.2111(6) 0.7574(4) 0.7976(4) 0.0889(14) Uani 1 1 d . . . O4 O 0.2824(5) 0.5852(4) 0.8590(4) 0.0820(12) Uani 1 1 d . . . O5 O -0.0869(8) 0.6171(5) 0.7002(4) 0.0998(17) Uani 1 1 d . . . O6 O -0.2843(6) 0.7423(5) 0.6943(4) 0.0965(16) Uani 1 1 d . B . C1 C -0.0163(6) 0.7074(4) 1.1220(4) 0.0525(12) Uani 1 1 d . . . H1 H -0.0460 0.6289 1.1151 0.063 Uiso 1 1 calc R . . C2 C 0.1259(6) 0.7256(4) 1.0525(4) 0.0473(12) Uani 1 1 d . . . C3 C 0.0676(6) 0.6655(4) 0.9310(4) 0.0491(12) Uani 1 1 d . . . H3 H 0.0564 0.5867 0.9469 0.059 Uiso 1 1 calc R . . C4 C -0.1045(6) 0.7082(4) 0.8744(4) 0.0523(12) Uani 1 1 d . . . C5 C -0.2087(7) 0.7564(5) 0.9337(5) 0.0619(15) Uani 1 1 d . . . H5 H -0.3108 0.7822 0.8918 0.074 Uiso 1 1 calc R . . C6 C -0.1722(7) 0.7721(5) 1.0650(4) 0.0608(14) Uani 1 1 d . . . H6A H -0.2679 0.7474 1.0970 0.073 Uiso 1 1 calc R . . H6B H -0.1550 0.8500 1.0830 0.073 Uiso 1 1 calc R . . C7 C 0.0357(7) 0.7326(5) 1.2521(4) 0.0584(13) Uani 1 1 d . . . C8 C 0.0740(9) 0.8375(6) 1.2919(6) 0.0708(17) Uani 1 1 d . . . H8 H 0.0701 0.8946 1.2379 0.085 Uiso 1 1 calc R . . C9 C 0.1183(10) 0.8612(6) 1.4103(5) 0.089(2) Uani 1 1 d . . . H9 H 0.1455 0.9333 1.4347 0.106 Uiso 1 1 calc R . . C10 C 0.1224(11) 0.7792(7) 1.4918(6) 0.091(2) Uani 1 1 d . . . H10 H 0.1524 0.7953 1.5714 0.110 Uiso 1 1 calc R . . C11 C 0.0817(9) 0.6723(7) 1.4553(5) 0.086(2) Uani 1 1 d . . . H11 H 0.0849 0.6163 1.5104 0.103 Uiso 1 1 calc R . . C12 C 0.0361(8) 0.6484(5) 1.3364(5) 0.0646(15) Uani 1 1 d . . . C13 C 0.1481(7) 0.8456(5) 1.0330(4) 0.0548(13) Uani 1 1 d . . . C14 C 0.2934(8) 0.6784(5) 1.1129(5) 0.0598(14) Uani 1 1 d . . . C15 C 0.4207(10) 0.5189(7) 1.2039(6) 0.096(2) Uani 1 1 d D . . H15A H 0.4828 0.5692 1.2614 0.116 Uiso 1 1 calc R . . H15B H 0.3846 0.4569 1.2459 0.116 Uiso 1 1 calc R . . C16 C 0.5255(15) 0.4810(13) 1.1319(11) 0.174(4) Uani 1 1 d DU . . H16A H 0.4621 0.4709 1.0539 0.261 Uiso 1 1 calc R . . H16B H 0.5741 0.4118 1.1612 0.261 Uiso 1 1 calc R . . H16C H 0.6133 0.5339 1.1304 0.261 Uiso 1 1 calc R . . C17 C 0.1951(8) 0.6770(5) 0.8545(5) 0.0625(14) Uani 1 1 d . . . C18 C 0.4126(13) 0.5862(9) 0.7853(10) 0.138(4) Uani 1 1 d D . . H18A H 0.3779 0.6345 0.7185 0.165 Uiso 1 1 calc R . . H18B H 0.5175 0.6140 0.8305 0.165 Uiso 1 1 calc R . . C19 C 0.4351(14) 0.4816(10) 0.7475(10) 0.150(4) Uani 1 1 d DU . . H19A H 0.4130 0.4294 0.8049 0.225 Uiso 1 1 calc R . . H19B H 0.5489 0.4732 0.7366 0.225 Uiso 1 1 calc R . . H19C H 0.3594 0.4687 0.6744 0.225 Uiso 1 1 calc R . . C20 C -0.1570(9) 0.6843(6) 0.7474(5) 0.0693(16) Uani 1 1 d . . . C21 C -0.3506(12) 0.7176(10) 0.5721(6) 0.136(4) Uani 1 1 d D . . H21A H -0.4220 0.6527 0.5648 0.163 Uiso 1 1 calc R A 1 H21B H -0.2604 0.7051 0.5296 0.163 Uiso 1 1 calc R A 1 H21C H -0.4613 0.6863 0.5623 0.163 Uiso 1 1 d R A 2 H21D H -0.2751 0.6678 0.5440 0.163 Uiso 1 1 d R A 2 C22 C -0.453(3) 0.8211(19) 0.526(2) 0.163(9) Uani 0.50 1 d PDU B 1 H22A H -0.5272 0.8397 0.5781 0.245 Uiso 0.50 1 calc PR B 1 H22B H -0.5169 0.8065 0.4492 0.245 Uiso 0.50 1 calc PR B 1 H22C H -0.3773 0.8816 0.5222 0.245 Uiso 0.50 1 calc PR B 1 C22' C -0.339(3) 0.8183(17) 0.5059(19) 0.137(7) Uani 0.50 1 d PDU B 2 H22D H -0.3785 0.8796 0.5459 0.206 Uiso 0.50 1 calc PR B 2 H22E H -0.4077 0.8113 0.4291 0.206 Uiso 0.50 1 calc PR B 2 H22F H -0.2247 0.8307 0.4992 0.206 Uiso 0.50 1 calc PR B 2 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 0.1342(6) 0.0631(4) 0.0713(4) 0.0134(4) 0.0359(3) -0.0093(4) N1 0.100(4) 0.052(3) 0.071(3) 0.003(2) 0.029(3) -0.005(3) O1 0.068(3) 0.077(3) 0.172(5) 0.010(4) -0.006(3) -0.005(3) O2 0.084(3) 0.055(2) 0.080(3) 0.006(2) 0.004(2) 0.004(2) O3 0.136(4) 0.071(3) 0.074(3) 0.004(2) 0.056(3) -0.015(3) O4 0.091(3) 0.078(3) 0.089(3) -0.001(2) 0.050(2) 0.007(2) O5 0.139(4) 0.104(4) 0.053(3) -0.012(3) 0.009(3) 0.008(4) O6 0.098(3) 0.128(4) 0.053(3) 0.012(3) -0.011(2) 0.019(3) C1 0.065(3) 0.051(3) 0.043(3) 0.002(2) 0.014(2) -0.001(3) C2 0.056(3) 0.044(3) 0.041(3) 0.004(2) 0.008(2) -0.001(2) C3 0.068(3) 0.041(3) 0.041(3) 0.004(2) 0.018(2) 0.001(2) C4 0.059(3) 0.054(3) 0.042(3) 0.002(2) 0.006(2) -0.003(3) C5 0.055(3) 0.070(4) 0.059(3) 0.011(3) 0.007(3) -0.001(3) C6 0.060(3) 0.074(4) 0.053(3) -0.005(3) 0.020(3) -0.002(3) C7 0.076(3) 0.061(4) 0.042(3) 0.001(3) 0.021(2) 0.003(3) C8 0.097(5) 0.065(4) 0.052(4) -0.003(3) 0.016(3) 0.003(3) C9 0.141(6) 0.072(4) 0.052(4) -0.007(3) 0.016(4) -0.004(4) C10 0.141(6) 0.088(5) 0.045(3) -0.003(3) 0.018(4) 0.011(5) C11 0.121(5) 0.091(5) 0.049(3) 0.021(3) 0.024(4) 0.016(4) C12 0.087(4) 0.064(4) 0.048(3) 0.008(3) 0.025(3) 0.010(3) C13 0.063(3) 0.057(4) 0.047(3) 0.001(2) 0.017(2) 0.002(3) C14 0.063(4) 0.059(4) 0.058(3) -0.003(3) 0.011(3) 0.002(3) C15 0.116(5) 0.071(5) 0.091(4) 0.000(4) -0.007(4) 0.015(4) C16 0.153(7) 0.166(9) 0.195(8) 0.014(8) 0.009(7) -0.013(7) C17 0.091(4) 0.053(3) 0.048(3) -0.011(3) 0.024(3) -0.002(3) C18 0.136(7) 0.119(8) 0.193(10) -0.036(7) 0.119(7) -0.011(6) C19 0.167(7) 0.143(8) 0.167(7) -0.024(7) 0.100(6) 0.011(6) C20 0.091(4) 0.066(4) 0.049(3) -0.003(3) 0.008(3) -0.003(3) C21 0.123(6) 0.203(11) 0.077(5) 0.024(7) 0.005(5) 0.036(7) C22 0.163(12) 0.180(13) 0.145(12) 0.014(9) 0.026(9) 0.016(9) C22' 0.145(11) 0.147(11) 0.118(10) 0.034(9) 0.021(8) -0.007(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 C12 1.895(6) . ? N1 C13 1.134(7) . ? O1 C14 1.187(7) . ? O2 C14 1.319(7) . ? O2 C15 1.415(7) . ? O3 C17 1.197(7) . ? O4 C17 1.313(7) . ? O4 C18 1.480(8) . ? O5 C20 1.185(8) . ? O6 C20 1.301(8) . ? O6 C21 1.448(9) . ? C1 C7 1.520(7) . ? C1 C6 1.526(7) . ? C1 C2 1.544(7) . ? C1 H1 0.9800 . ? C2 C13 1.486(8) . ? C2 C14 1.516(8) . ? C2 C3 1.577(7) . ? C3 C17 1.493(8) . ? C3 C4 1.515(7) . ? C3 H3 0.9800 . ? C4 C5 1.323(8) . ? C4 C20 1.483(8) . ? C5 C6 1.509(8) . ? C5 H5 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.367(9) . ? C7 C12 1.413(8) . ? C8 C9 1.383(9) . ? C8 H8 0.9300 . ? C9 C10 1.368(10) . ? C9 H9 0.9300 . ? C10 C11 1.381(10) . ? C10 H10 0.9300 . ? C11 C12 1.390(9) . ? C11 H11 0.9300 . ? C15 C16 1.381(13) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C18 C19 1.364(12) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C21 C22' 1.454(16) . ? C21 C22 1.539(17) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9600 . ? C21 H21D 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C22' H22D 0.9600 . ? C22' H22E 0.9600 . ? C22' H22F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O2 C15 118.0(5) . . ? C17 O4 C18 114.1(6) . . ? C20 O6 C21 117.7(6) . . ? C7 C1 C6 112.1(4) . . ? C7 C1 C2 113.5(4) . . ? C6 C1 C2 109.9(4) . . ? C7 C1 H1 107.0 . . ? C6 C1 H1 107.0 . . ? C2 C1 H1 107.0 . . ? C13 C2 C14 108.4(4) . . ? C13 C2 C1 110.0(4) . . ? C14 C2 C1 113.4(4) . . ? C13 C2 C3 109.8(4) . . ? C14 C2 C3 109.2(4) . . ? C1 C2 C3 106.0(4) . . ? C17 C3 C4 113.3(4) . . ? C17 C3 C2 111.5(4) . . ? C4 C3 C2 108.9(4) . . ? C17 C3 H3 107.6 . . ? C4 C3 H3 107.6 . . ? C2 C3 H3 107.6 . . ? C5 C4 C20 120.9(5) . . ? C5 C4 C3 123.5(5) . . ? C20 C4 C3 115.5(5) . . ? C4 C5 C6 124.1(5) . . ? C4 C5 H5 117.9 . . ? C6 C5 H5 117.9 . . ? C5 C6 C1 111.0(5) . . ? C5 C6 H6A 109.4 . . ? C1 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? C1 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C12 117.8(5) . . ? C8 C7 C1 121.6(5) . . ? C12 C7 C1 120.5(5) . . ? C7 C8 C9 121.9(6) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C10 C9 C8 120.3(7) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 119.6(6) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 120.2(6) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 120.2(6) . . ? C11 C12 Br1 117.3(5) . . ? C7 C12 Br1 122.5(4) . . ? N1 C13 C2 177.5(6) . . ? O1 C14 O2 125.6(5) . . ? O1 C14 C2 123.6(5) . . ? O2 C14 C2 110.7(5) . . ? C16 C15 O2 112.5(8) . . ? C16 C15 H15A 109.1 . . ? O2 C15 H15A 109.1 . . ? C16 C15 H15B 109.1 . . ? O2 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? 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 . . ? O3 C17 O4 126.6(6) . . ? O3 C17 C3 124.4(6) . . ? O4 C17 C3 109.1(5) . . ? C19 C18 O4 109.5(8) . . ? C19 C18 H18A 109.8 . . ? O4 C18 H18A 109.8 . . ? C19 C18 H18B 109.8 . . ? O4 C18 H18B 109.8 . . ? H18A C18 H18B 108.2 . . ? 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 . . ? O5 C20 O6 123.9(6) . . ? O5 C20 C4 121.5(6) . . ? O6 C20 C4 114.6(6) . . ? O6 C21 C22' 107.2(13) . . ? O6 C21 C22 104.2(13) . . ? C22' C21 C22 38.5(12) . . ? O6 C21 H21A 110.9 . . ? C22' C21 H21A 136.9 . . ? C22 C21 H21A 110.9 . . ? O6 C21 H21B 110.9 . . ? C22' C21 H21B 74.4 . . ? C22 C21 H21B 110.9 . . ? H21A C21 H21B 108.9 . . ? O6 C21 H21C 111.1 . . ? C22' C21 H21C 114.8 . . ? C22 C21 H21C 81.5 . . ? H21A C21 H21C 30.9 . . ? H21B C21 H21C 131.0 . . ? O6 C21 H21D 108.8 . . ? C22' C21 H21D 103.7 . . ? C22 C21 H21D 136.7 . . ? H21A C21 H21D 82.6 . . ? H21B C21 H21D 30.2 . . ? H21C C21 H21D 110.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? C21 C22' H22D 109.5 . . ? C21 C22' H22E 109.5 . . ? H22D C22' H22E 109.5 . . ? C21 C22' H22F 109.5 . . ? H22D C22' H22F 109.5 . . ? H22E C22' H22F 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 C7 C1 C2 C13 -76.6(5) . . . . ? C6 C1 C2 C13 49.9(5) . . . . ? C7 C1 C2 C14 44.9(6) . . . . ? C6 C1 C2 C14 171.4(4) . . . . ? C7 C1 C2 C3 164.7(4) . . . . ? C6 C1 C2 C3 -68.8(5) . . . . ? C13 C2 C3 C17 61.1(6) . . . . ? C14 C2 C3 C17 -57.6(6) . . . . ? C1 C2 C3 C17 179.9(4) . . . . ? C13 C2 C3 C4 -64.7(5) . . . . ? C14 C2 C3 C4 176.7(4) . . . . ? C1 C2 C3 C4 54.2(5) . . . . ? C17 C3 C4 C5 -145.9(5) . . . . ? C2 C3 C4 C5 -21.2(7) . . . . ? C17 C3 C4 C20 39.1(7) . . . . ? C2 C3 C4 C20 163.8(5) . . . . ? C20 C4 C5 C6 172.9(6) . . . . ? C3 C4 C5 C6 -1.8(9) . . . . ? C4 C5 C6 C1 -10.3(8) . . . . ? C7 C1 C6 C5 173.1(5) . . . . ? C2 C1 C6 C5 45.9(6) . . . . ? C6 C1 C7 C8 -58.5(7) . . . . ? C2 C1 C7 C8 66.8(7) . . . . ? C6 C1 C7 C12 117.7(6) . . . . ? C2 C1 C7 C12 -117.0(5) . . . . ? C12 C7 C8 C9 2.5(10) . . . . ? C1 C7 C8 C9 178.8(6) . . . . ? C7 C8 C9 C10 -1.0(12) . . . . ? C8 C9 C10 C11 -0.1(12) . . . . ? C9 C10 C11 C12 -0.3(12) . . . . ? C10 C11 C12 C7 1.8(10) . . . . ? C10 C11 C12 Br1 -177.7(6) . . . . ? C8 C7 C12 C11 -2.8(9) . . . . ? C1 C7 C12 C11 -179.2(6) . . . . ? C8 C7 C12 Br1 176.6(5) . . . . ? C1 C7 C12 Br1 0.3(8) . . . . ? C14 C2 C13 N1 -118(14) . . . . ? C1 C2 C13 N1 6(14) . . . . ? C3 C2 C13 N1 123(14) . . . . ? C15 O2 C14 O1 1.6(9) . . . . ? C15 O2 C14 C2 -176.6(5) . . . . ? C13 C2 C14 O1 -3.3(8) . . . . ? C1 C2 C14 O1 -125.8(6) . . . . ? C3 C2 C14 O1 116.2(6) . . . . ? C13 C2 C14 O2 174.8(4) . . . . ? C1 C2 C14 O2 52.4(6) . . . . ? C3 C2 C14 O2 -65.6(6) . . . . ? C14 O2 C15 C16 -82.2(10) . . . . ? C18 O4 C17 O3 0.5(9) . . . . ? C18 O4 C17 C3 179.5(6) . . . . ? C4 C3 C17 O3 43.3(8) . . . . ? C2 C3 C17 O3 -79.9(7) . . . . ? C4 C3 C17 O4 -135.7(5) . . . . ? C2 C3 C17 O4 101.0(5) . . . . ? C17 O4 C18 C19 -149.5(10) . . . . ? C21 O6 C20 O5 4.3(11) . . . . ? C21 O6 C20 C4 -175.4(7) . . . . ? C5 C4 C20 O5 -159.5(7) . . . . ? C3 C4 C20 O5 15.6(9) . . . . ? C5 C4 C20 O6 20.3(8) . . . . ? C3 C4 C20 O6 -164.6(5) . . . . ? C20 O6 C21 C22' -121.5(13) . . . . ? C20 O6 C21 C22 -161.4(13) . . . . ? 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 C10 H10 O3 0.93 2.62 3.496(8) 157.3 1_556 C16 H16B O3 0.96 2.54 3.447(15) 158.4 2_647 C6 H6A O1 0.97 2.66 3.589(8) 160.6 1_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.529 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.071