# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © 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 ramsc@uohyd.ernet.in _publ_contact_author_name 'Dhevalapally B. Ramachary' loop_ _publ_author_name 'Dhevalapally B. Ramachary' 'Y. Vijayendar Reddy' data_yvr-v-106 _database_code_depnum_ccdc_archive 'CCDC 828199' #TrackingRef 'DBR-26.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H31 Br N2 O8' _chemical_formula_sum 'C25 H31 Br N2 O8' _chemical_formula_weight 567.43 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.5256(2) _cell_length_b 12.1392(2) _cell_length_c 20.3601(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2601.46(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4796 _cell_measurement_theta_min 3.6381 _cell_measurement_theta_max 58.8247 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 2.590 _exptl_absorpt_correction_T_min 0.50514 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.3291 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4127 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0088 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.24 _diffrn_reflns_theta_max 58.90 _reflns_number_total 2927 _reflns_number_gt 2922 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+2.5159P] 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 0.110(19) _refine_ls_number_reflns 2927 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.008 _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 C21 C 0.3255(3) 0.9992(3) 1.07633(18) 0.0179(8) Uani 1 1 d . . . C23 C 0.3396(3) 0.8580(3) 0.98454(17) 0.0140(7) Uani 1 1 d . . . H23 H 0.4029 0.8146 1.0104 0.017 Uiso 1 1 calc R . . C20 C 0.4095(4) 1.0780(3) 1.03885(18) 0.0210(8) Uani 1 1 d . . . H20A H 0.4635 1.1190 1.0703 0.025 Uiso 1 1 calc R . . H20B H 0.3556 1.1321 1.0154 0.025 Uiso 1 1 calc R . . C22 C 0.2551(3) 0.9160(3) 1.03544(17) 0.0179(8) Uani 1 1 d . . . H22A H 0.1846 0.9535 1.0123 0.021 Uiso 1 1 calc R . . H22B H 0.2176 0.8599 1.0649 0.021 Uiso 1 1 calc R . . C19 C 0.4941(3) 1.0187(3) 0.98933(17) 0.0176(8) Uani 1 1 d . . . H19 H 0.5517 0.9704 1.0156 0.021 Uiso 1 1 calc R . . O3 O 0.4629(3) 0.9365(2) 0.74009(11) 0.0270(6) Uani 1 1 d . . . O2 O 0.2488(2) 1.0620(2) 0.91720(12) 0.0195(6) Uani 1 1 d . . . O1 O 0.5963(2) 0.8176(2) 0.93724(12) 0.0202(6) Uani 1 1 d . . . O8 O 0.1496(2) 0.7789(2) 0.78808(12) 0.0193(6) Uani 1 1 d . . . O7 O 0.2797(3) 0.5622(2) 0.88468(12) 0.0219(6) Uani 1 1 d . . . O4 O 0.3100(3) 1.0059(2) 1.13512(12) 0.0226(6) Uani 1 1 d . . . C30 C 0.4009(4) 0.5243(3) 0.9076(2) 0.0294(9) Uani 1 1 d . . . H30A H 0.4414 0.5823 0.9337 0.044 Uiso 1 1 calc R . . H30B H 0.4549 0.5063 0.8699 0.044 Uiso 1 1 calc R . . H30C H 0.3891 0.4585 0.9348 0.044 Uiso 1 1 calc R . . C33 C 0.0741(4) 0.5889(3) 0.80045(19) 0.0265(9) Uani 1 1 d . . . H33A H 0.1075 0.5756 0.7562 0.040 Uiso 1 1 calc R . . H33B H -0.0171 0.6046 0.7978 0.040 Uiso 1 1 calc R . . H33C H 0.0878 0.5234 0.8277 0.040 Uiso 1 1 calc R . . C32 C 0.0300(4) 0.8194(3) 0.76540(19) 0.0294(9) Uani 1 1 d . . . H32A H -0.0246 0.8359 0.8031 0.044 Uiso 1 1 calc R . . H32B H -0.0108 0.7635 0.7378 0.044 Uiso 1 1 calc R . . H32C H 0.0433 0.8866 0.7397 0.044 Uiso 1 1 calc R . . C31 C 0.3680(4) 0.6547(3) 0.78780(17) 0.0195(8) Uani 1 1 d . . . H31A H 0.4549 0.6371 0.8014 0.029 Uiso 1 1 calc R . . H31B H 0.3674 0.7254 0.7646 0.029 Uiso 1 1 calc R . . H31C H 0.3363 0.5968 0.7585 0.029 Uiso 1 1 calc R . . C34 C 0.2631(4) 1.0568(3) 0.78695(19) 0.0281(9) Uani 1 1 d . . . H34A H 0.2755 1.1364 0.7918 0.042 Uiso 1 1 calc R . . H34B H 0.1764 1.0374 0.8000 0.042 Uiso 1 1 calc R . . H34C H 0.2768 1.0358 0.7410 0.042 Uiso 1 1 calc R . . C35 C 0.6530(4) 0.8400(4) 0.8100(2) 0.0298(10) Uani 1 1 d . . . H35A H 0.6387 0.7603 0.8074 0.045 Uiso 1 1 calc R . . H35B H 0.7290 0.8546 0.8364 0.045 Uiso 1 1 calc R . . H35C H 0.6650 0.8696 0.7656 0.045 Uiso 1 1 calc R . . Br1 Br 0.96407(4) 1.10468(3) 0.90643(2) 0.02628(13) Uani 1 1 d . . . O6 O 0.0744(2) 0.71424(19) 0.88882(11) 0.0187(5) Uani 1 1 d . . . N2 N 0.5425(3) 0.8929(2) 0.84066(13) 0.0181(6) Uani 1 1 d . . . O5 O 0.3343(2) 0.74788(18) 0.88703(11) 0.0146(5) Uani 1 1 d . . . C13 C 0.3336(3) 1.0051(3) 0.89572(17) 0.0140(8) Uani 1 1 d . . . N1 N 0.3543(3) 0.9979(2) 0.82896(14) 0.0155(6) Uani 1 1 d . . . C5 C 0.5793(3) 1.0965(3) 0.95188(16) 0.0147(7) Uani 1 1 d . . . C8 C 0.1299(3) 0.8044(3) 0.92402(17) 0.0173(8) Uani 1 1 d . . . H8A H 0.0775 0.8219 0.9630 0.021 Uiso 1 1 calc R . . H8B H 0.1330 0.8704 0.8956 0.021 Uiso 1 1 calc R . . C1 C 0.7870(3) 1.1388(3) 0.90990(18) 0.0170(8) Uani 1 1 d . . . C15 C 0.4533(4) 0.9414(3) 0.79916(16) 0.0178(8) Uani 1 1 d . . . C7 C 0.2624(3) 0.7731(3) 0.94518(17) 0.0155(7) Uani 1 1 d . . . H7 H 0.2564 0.7044 0.9721 0.019 Uiso 1 1 calc R . . C3 C 0.6145(4) 1.2555(3) 0.88249(17) 0.0183(8) Uani 1 1 d . . . H3 H 0.5816 1.3183 0.8605 0.022 Uiso 1 1 calc R . . C2 C 0.7430(4) 1.2300(3) 0.87660(17) 0.0183(8) Uani 1 1 d . . . H2 H 0.7983 1.2738 0.8506 0.022 Uiso 1 1 calc R . . C10 C 0.1425(4) 0.6868(3) 0.83092(17) 0.0176(8) Uani 1 1 d . . . C6 C 0.7083(3) 1.0720(3) 0.94664(17) 0.0155(8) Uani 1 1 d . . . H6 H 0.7420 1.0093 0.9684 0.019 Uiso 1 1 calc R . . C11 C 0.2837(4) 0.6620(3) 0.84766(17) 0.0153(7) Uani 1 1 d . . . C4 C 0.5347(4) 1.1909(3) 0.91968(15) 0.0166(7) Uani 1 1 d . . . H4 H 0.4477 1.2106 0.9236 0.020 Uiso 1 1 calc R . . C17 C 0.5247(3) 0.8758(3) 0.90691(16) 0.0143(7) Uani 1 1 d . . . C18 C 0.4191(3) 0.9396(3) 0.94138(16) 0.0126(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C21 0.0188(18) 0.0148(16) 0.0201(19) -0.0001(15) 0.0029(16) 0.0009(16) C23 0.0171(18) 0.0126(16) 0.0123(16) 0.0001(13) 0.0016(15) -0.0010(15) C20 0.0219(18) 0.0219(19) 0.0193(17) -0.0064(15) -0.0006(16) -0.0013(16) C22 0.0175(18) 0.0178(18) 0.0183(17) 0.0037(15) 0.0020(16) 0.0005(16) C19 0.018(2) 0.0221(17) 0.0129(16) -0.0005(14) -0.0010(14) -0.0012(16) O3 0.0423(16) 0.0249(13) 0.0139(12) -0.0001(10) 0.0038(14) -0.0090(14) O2 0.0145(12) 0.0189(12) 0.0251(14) 0.0025(11) 0.0010(12) 0.0040(11) O1 0.0167(12) 0.0202(12) 0.0238(13) 0.0033(11) -0.0023(12) 0.0046(11) O8 0.0187(13) 0.0199(12) 0.0193(12) 0.0033(11) -0.0021(11) 0.0031(11) O7 0.0302(15) 0.0129(11) 0.0226(13) 0.0022(10) -0.0012(12) 0.0000(11) O4 0.0301(14) 0.0231(13) 0.0146(13) -0.0011(10) 0.0050(12) 0.0025(13) C30 0.041(2) 0.0245(19) 0.0232(19) 0.0059(17) 0.000(2) 0.0169(19) C33 0.025(2) 0.025(2) 0.030(2) -0.0058(17) 0.0003(17) -0.0058(18) C32 0.028(2) 0.035(2) 0.0254(19) 0.0048(17) -0.006(2) 0.011(2) C31 0.0232(19) 0.0152(16) 0.0201(18) -0.0033(15) 0.0030(17) 0.0024(17) C34 0.030(2) 0.032(2) 0.0220(19) 0.0074(18) -0.0081(18) -0.005(2) C35 0.025(2) 0.034(2) 0.030(2) -0.0010(19) 0.0158(19) 0.002(2) Br1 0.0150(2) 0.0264(2) 0.0374(2) 0.00409(18) 0.00299(18) 0.00189(17) O6 0.0178(13) 0.0171(12) 0.0212(12) -0.0032(10) 0.0021(10) -0.0047(11) N2 0.0187(15) 0.0149(13) 0.0206(15) -0.0012(13) 0.0080(14) 0.0012(16) O5 0.0152(12) 0.0125(11) 0.0160(12) -0.0020(9) 0.0023(10) -0.0008(10) C13 0.0157(18) 0.0113(15) 0.0151(17) 0.0012(15) 0.0002(15) -0.0016(16) N1 0.0180(15) 0.0121(14) 0.0165(14) -0.0005(12) -0.0024(13) -0.0014(13) C5 0.0146(17) 0.0166(17) 0.0129(15) -0.0048(15) -0.0014(14) -0.0042(15) C8 0.0163(18) 0.0144(16) 0.0213(18) -0.0049(14) 0.0019(15) -0.0036(15) C1 0.0074(16) 0.0222(18) 0.0214(18) -0.0055(16) 0.0002(16) 0.0017(14) C15 0.025(2) 0.0096(15) 0.0187(18) -0.0006(14) 0.0027(17) -0.0089(17) C7 0.0185(18) 0.0114(16) 0.0166(18) 0.0007(14) 0.0030(16) -0.0032(15) C3 0.026(2) 0.0115(16) 0.0179(17) 0.0000(14) -0.0041(16) 0.0020(17) C2 0.023(2) 0.0122(16) 0.0200(17) -0.0013(15) 0.0005(16) -0.0062(16) C10 0.0195(19) 0.0141(16) 0.0193(17) 0.0012(15) 0.0007(16) -0.0026(16) C6 0.0186(19) 0.0126(16) 0.0154(17) 0.0002(14) -0.0055(15) -0.0012(15) C11 0.0220(19) 0.0075(15) 0.0165(17) -0.0019(14) 0.0009(16) -0.0002(15) C4 0.0136(17) 0.0162(16) 0.0202(17) -0.0065(14) 0.0031(16) -0.0013(16) C17 0.0154(16) 0.0111(15) 0.0165(16) -0.0005(14) 0.0000(17) -0.0026(15) C18 0.0129(16) 0.0125(15) 0.0123(16) 0.0004(14) 0.0018(15) 0.0001(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C21 O4 1.211(4) . ? C21 C22 1.503(5) . ? C21 C20 1.510(5) . ? C23 C22 1.536(5) . ? C23 C7 1.537(5) . ? C23 C18 1.566(5) . ? C23 H23 1.0000 . ? C20 C19 1.525(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C19 C5 1.509(5) . ? C19 C18 1.580(5) . ? C19 H19 1.0000 . ? O3 C15 1.208(4) . ? O2 C13 1.210(4) . ? O1 C17 1.204(4) . ? O8 C10 1.420(4) . ? O8 C32 1.428(5) . ? O7 C11 1.427(4) . ? O7 C30 1.433(5) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C33 C10 1.522(5) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C31 C11 1.510(5) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C34 N1 1.471(5) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 N2 1.469(5) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? Br1 C1 1.910(3) . ? O6 C10 1.419(4) . ? O6 C8 1.432(4) . ? N2 C17 1.378(4) . ? N2 C15 1.393(5) . ? O5 C11 1.419(4) . ? O5 C7 1.438(4) . ? C13 N1 1.379(5) . ? C13 C18 1.518(5) . ? N1 C15 1.387(5) . ? C5 C6 1.394(5) . ? C5 C4 1.401(5) . ? C8 C7 1.509(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C1 C2 1.379(5) . ? C1 C6 1.379(5) . ? C7 H7 1.0000 . ? C3 C4 1.377(5) . ? C3 C2 1.392(6) . ? C3 H3 0.9500 . ? C2 H2 0.9500 . ? C10 C11 1.554(5) . ? C6 H6 0.9500 . ? C4 H4 0.9500 . ? C17 C18 1.526(5) . ? 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 O4 C21 C22 121.8(3) . . ? O4 C21 C20 122.4(3) . . ? C22 C21 C20 115.7(3) . . ? C22 C23 C7 110.7(3) . . ? C22 C23 C18 113.4(3) . . ? C7 C23 C18 114.4(3) . . ? C22 C23 H23 105.8 . . ? C7 C23 H23 105.8 . . ? C18 C23 H23 105.8 . . ? C21 C20 C19 112.1(3) . . ? C21 C20 H20A 109.2 . . ? C19 C20 H20A 109.2 . . ? C21 C20 H20B 109.2 . . ? C19 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C21 C22 C23 113.4(3) . . ? C21 C22 H22A 108.9 . . ? C23 C22 H22A 108.9 . . ? C21 C22 H22B 108.9 . . ? C23 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? C5 C19 C20 112.7(3) . . ? C5 C19 C18 111.4(3) . . ? C20 C19 C18 113.8(3) . . ? C5 C19 H19 106.1 . . ? C20 C19 H19 106.1 . . ? C18 C19 H19 106.1 . . ? C10 O8 C32 115.1(3) . . ? C11 O7 C30 114.8(3) . . ? O7 C30 H30A 109.5 . . ? O7 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O7 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C10 C33 H33A 109.5 . . ? C10 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C10 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O8 C32 H32A 109.5 . . ? O8 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O8 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C11 C31 H31A 109.5 . . ? C11 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C11 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N1 C34 H34A 109.5 . . ? N1 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N1 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N2 C35 H35A 109.5 . . ? N2 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N2 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C10 O6 C8 112.9(3) . . ? C17 N2 C15 124.5(3) . . ? C17 N2 C35 117.3(3) . . ? C15 N2 C35 117.4(3) . . ? C11 O5 C7 115.1(3) . . ? O2 C13 N1 120.6(3) . . ? O2 C13 C18 120.9(3) . . ? N1 C13 C18 118.5(3) . . ? C13 N1 C15 125.5(3) . . ? C13 N1 C34 116.1(3) . . ? C15 N1 C34 118.4(3) . . ? C6 C5 C4 117.7(3) . . ? C6 C5 C19 119.0(3) . . ? C4 C5 C19 123.3(3) . . ? O6 C8 C7 109.2(3) . . ? O6 C8 H8A 109.8 . . ? C7 C8 H8A 109.8 . . ? O6 C8 H8B 109.8 . . ? C7 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? C2 C1 C6 122.4(3) . . ? C2 C1 Br1 118.9(3) . . ? C6 C1 Br1 118.6(3) . . ? O3 C15 N1 121.5(4) . . ? O3 C15 N2 121.8(4) . . ? N1 C15 N2 116.7(3) . . ? O5 C7 C8 107.7(3) . . ? O5 C7 C23 107.1(3) . . ? C8 C7 C23 118.0(3) . . ? O5 C7 H7 107.9 . . ? C8 C7 H7 107.9 . . ? C23 C7 H7 107.9 . . ? C4 C3 C2 120.9(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C1 C2 C3 117.6(3) . . ? C1 C2 H2 121.2 . . ? C3 C2 H2 121.2 . . ? O8 C10 O6 110.6(3) . . ? O8 C10 C33 112.9(3) . . ? O6 C10 C33 106.4(3) . . ? O8 C10 C11 103.7(3) . . ? O6 C10 C11 110.3(3) . . ? C33 C10 C11 113.0(3) . . ? C1 C6 C5 120.1(3) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? O5 C11 O7 109.6(3) . . ? O5 C11 C31 106.2(3) . . ? O7 C11 C31 113.2(3) . . ? O5 C11 C10 109.9(3) . . ? O7 C11 C10 104.6(3) . . ? C31 C11 C10 113.3(3) . . ? C3 C4 C5 121.2(3) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? O1 C17 N2 120.4(3) . . ? O1 C17 C18 121.2(3) . . ? N2 C17 C18 118.2(3) . . ? C13 C18 C17 114.6(3) . . ? C13 C18 C23 111.0(3) . . ? C17 C18 C23 109.0(3) . . ? C13 C18 C19 110.9(3) . . ? C17 C18 C19 103.2(3) . . ? C23 C18 C19 107.7(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 58.90 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.594 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.067 # Attachment 'dbr24.cif' data_yvr-v-151 _database_code_depnum_ccdc_archive 'CCDC 828200' #TrackingRef 'dbr24.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 Br N2 O6' _chemical_formula_weight 493.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.6547(9) _cell_length_b 10.4150(9) _cell_length_c 13.3157(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.10 _cell_angle_gamma 90.00 _cell_volume 1061.58(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5211 _cell_measurement_theta_min 3.3163 _cell_measurement_theta_max 69.6075 _chemical_absolute_configuration rm _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 3.008 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3792 _exptl_absorpt_correction_T_max 0.7332 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5241 _diffrn_reflns_av_R_equivalents 0.0819 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 65.05 _reflns_number_total 3117 _reflns_number_gt 3010 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0727P)^2^+7.0849P] 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 0.14(4) _refine_ls_number_reflns 3117 _refine_ls_number_parameters 285 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1686 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.22835(13) -0.45221(8) 0.19748(7) 0.0423(3) Uani 1 1 d . . . C1 C 0.0476(12) 0.1136(8) 0.4800(6) 0.0305(18) Uani 1 1 d . . . C2 C 0.2132(10) 0.1883(8) 0.4728(6) 0.0266(16) Uani 1 1 d . . . H2A H 0.3073 0.1393 0.5065 0.032 Uiso 1 1 calc R . . H2B H 0.1984 0.2701 0.5096 0.032 Uiso 1 1 calc R . . C3 C 0.2715(11) 0.2188(7) 0.3638(6) 0.0292(17) Uani 1 1 d . . . H3 H 0.1801 0.2784 0.3372 0.035 Uiso 1 1 calc R . . C4 C 0.2662(9) 0.1011(7) 0.2926(5) 0.0182(14) Uani 1 1 d . . . C5 C 0.0769(9) 0.0353(8) 0.3019(5) 0.0219(15) Uani 1 1 d . . . H5 H -0.0091 0.1020 0.2801 0.026 Uiso 1 1 calc R . . C6 C 0.0298(12) 0.0021(7) 0.4085(6) 0.0288(17) Uani 1 1 d . . . H6A H 0.1060 -0.0688 0.4318 0.035 Uiso 1 1 calc R . . H6B H -0.0924 -0.0291 0.4101 0.035 Uiso 1 1 calc R . . C7 C 0.0598(10) -0.0747(6) 0.2265(5) 0.0189(14) Uani 1 1 d . . . C8 C -0.0161(10) -0.0498(8) 0.1347(6) 0.0290(17) Uani 1 1 d . . . H8 H -0.0627 0.0329 0.1207 0.035 Uiso 1 1 calc R . . C9 C -0.0238(13) -0.1448(8) 0.0637(7) 0.038(2) Uani 1 1 d . . . H9 H -0.0807 -0.1287 0.0015 0.045 Uiso 1 1 calc R . . C10 C 0.0516(13) -0.2669(8) 0.0818(8) 0.040(2) Uani 1 1 d . . . H10 H 0.0537 -0.3306 0.0307 0.048 Uiso 1 1 calc R . . C11 C 0.1220(10) -0.2908(8) 0.1751(6) 0.0304(17) Uani 1 1 d . . . C12 C 0.1270(10) -0.1963(6) 0.2470(5) 0.0196(15) Uani 1 1 d . . . H12 H 0.1765 -0.2138 0.3110 0.024 Uiso 1 1 calc R . . C13 C 0.2795(9) 0.1472(7) 0.1852(5) 0.0187(14) Uani 1 1 d . . . C14 C 0.4873(10) -0.0215(7) 0.1410(6) 0.0219(15) Uani 1 1 d . . . C15 C 0.4034(11) -0.0026(7) 0.3169(6) 0.0231(16) Uani 1 1 d . . . C16 C 0.3880(11) 0.1282(9) 0.0136(5) 0.034(2) Uani 1 1 d . . . H16A H 0.2790 0.1021 -0.0192 0.052 Uiso 1 1 calc R . . H16B H 0.4871 0.0876 -0.0204 0.052 Uiso 1 1 calc R . . H16C H 0.4001 0.2217 0.0100 0.052 Uiso 1 1 calc R . . C17 C 0.5978(12) -0.1719(8) 0.2637(7) 0.0326(19) Uani 1 1 d . . . H17A H 0.6497 -0.1634 0.3307 0.049 Uiso 1 1 calc R . . H17B H 0.6908 -0.1796 0.2136 0.049 Uiso 1 1 calc R . . H17C H 0.5239 -0.2487 0.2615 0.049 Uiso 1 1 calc R . . C18 C 0.4395(11) 0.2978(8) 0.3646(6) 0.0294(17) Uani 1 1 d . . . H18 H 0.4164 0.3817 0.3985 0.035 Uiso 1 1 calc R . . C19 C 0.6064(11) 0.2357(9) 0.4118(6) 0.0321(18) Uani 1 1 d . . . H19A H 0.6503 0.2877 0.4687 0.039 Uiso 1 1 calc R . . H19B H 0.5819 0.1475 0.4357 0.039 Uiso 1 1 calc R . . C20 C 0.6711(13) 0.3344(9) 0.2613(7) 0.038(2) Uani 1 1 d . . . C21 C 0.7421(12) 0.2962(10) 0.1577(8) 0.046(2) Uani 1 1 d . . . H21A H 0.6984 0.2108 0.1398 0.069 Uiso 1 1 calc R . . H21B H 0.8701 0.2946 0.1599 0.069 Uiso 1 1 calc R . . H21C H 0.7033 0.3588 0.1075 0.069 Uiso 1 1 calc R . . C22 C 0.7356(13) 0.4679(10) 0.2944(9) 0.053(3) Uani 1 1 d . . . H22A H 0.6990 0.5322 0.2449 0.080 Uiso 1 1 calc R . . H22B H 0.8634 0.4673 0.2993 0.080 Uiso 1 1 calc R . . H22C H 0.6856 0.4891 0.3600 0.080 Uiso 1 1 calc R . . N1 N 0.3850(9) 0.0875(6) 0.1199(4) 0.0230(14) Uani 1 1 d . . . N2 N 0.4907(8) -0.0573(6) 0.2414(5) 0.0249(13) Uani 1 1 d . . . O1 O -0.0615(9) 0.1387(7) 0.5421(5) 0.0454(16) Uani 1 1 d . . . O2 O 0.4177(9) -0.0393(5) 0.4037(4) 0.0350(14) Uani 1 1 d . . . O3 O 0.5622(10) -0.0788(6) 0.0776(5) 0.0465(17) Uani 1 1 d . . . O4 O 0.4922(7) 0.3215(5) 0.2640(4) 0.0259(11) Uani 1 1 d . . . O5 O 0.7298(9) 0.2342(7) 0.3311(5) 0.0466(16) Uani 1 1 d . . . O6 O 0.1810(7) 0.2334(5) 0.1556(4) 0.0280(12) 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 0.0572(6) 0.0167(4) 0.0529(5) -0.0012(4) 0.0124(4) 0.0038(5) C1 0.048(5) 0.024(4) 0.019(4) -0.001(3) -0.002(3) 0.011(4) C2 0.029(4) 0.028(4) 0.022(4) -0.007(3) -0.002(3) 0.000(3) C3 0.036(4) 0.015(3) 0.037(4) -0.009(3) -0.002(3) -0.006(3) C4 0.021(4) 0.010(3) 0.024(4) -0.003(3) 0.004(3) -0.005(3) C5 0.025(3) 0.008(3) 0.032(3) -0.007(3) -0.002(3) 0.010(3) C6 0.034(4) 0.019(3) 0.033(4) -0.003(3) -0.002(3) -0.001(3) C7 0.030(4) 0.010(3) 0.017(3) 0.003(3) -0.001(3) 0.003(3) C8 0.028(4) 0.024(4) 0.035(4) 0.002(3) -0.001(3) -0.008(3) C9 0.050(6) 0.028(4) 0.036(4) 0.017(4) -0.017(4) -0.004(4) C10 0.047(5) 0.015(4) 0.058(6) -0.016(4) 0.010(4) -0.004(4) C11 0.026(4) 0.031(4) 0.034(4) 0.001(3) 0.006(3) -0.015(3) C12 0.023(4) 0.010(3) 0.026(4) 0.008(3) 0.005(3) -0.001(3) C13 0.021(3) 0.010(3) 0.024(4) 0.005(3) 0.000(3) -0.008(3) C14 0.021(4) 0.013(3) 0.032(4) -0.006(3) -0.003(3) 0.003(3) C15 0.034(4) 0.006(3) 0.030(4) 0.001(3) -0.005(3) -0.009(3) C16 0.038(5) 0.052(5) 0.014(4) 0.012(3) 0.011(3) 0.013(4) C17 0.030(5) 0.025(4) 0.043(5) 0.009(3) 0.001(4) 0.011(4) C18 0.033(4) 0.022(4) 0.033(4) -0.012(3) 0.007(3) -0.003(3) C19 0.036(4) 0.035(5) 0.026(4) -0.002(3) 0.002(3) 0.002(4) C20 0.049(6) 0.029(5) 0.036(4) -0.003(4) -0.001(4) 0.009(4) C21 0.030(5) 0.049(6) 0.059(6) 0.005(5) 0.033(4) -0.002(4) C22 0.033(5) 0.046(6) 0.081(8) -0.022(5) 0.001(5) -0.022(5) N1 0.036(4) 0.024(3) 0.008(3) 0.002(2) 0.004(2) -0.004(3) N2 0.028(3) 0.017(3) 0.029(3) 0.000(2) 0.003(3) 0.009(3) O1 0.042(4) 0.060(4) 0.034(3) -0.014(3) 0.009(3) 0.002(3) O2 0.059(4) 0.024(3) 0.022(3) 0.007(2) -0.002(3) 0.005(3) O3 0.058(4) 0.042(4) 0.040(4) -0.006(3) 0.011(3) 0.011(3) O4 0.020(3) 0.022(3) 0.036(3) 0.001(2) -0.003(2) 0.006(2) O5 0.046(4) 0.048(4) 0.046(4) 0.008(3) 0.005(3) 0.014(3) O6 0.035(3) 0.022(3) 0.027(3) 0.015(2) 0.002(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C11 1.891(9) . ? C1 O1 1.205(11) . ? C1 C2 1.490(12) . ? C1 C6 1.508(11) . ? C2 C3 1.551(11) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C18 1.527(11) . ? C3 C4 1.550(10) . ? C3 H3 1.0000 . ? C4 C13 1.512(10) . ? C4 C15 1.541(10) . ? C4 C5 1.607(10) . ? C5 C6 1.506(11) . ? C5 C7 1.530(10) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.377(11) . ? C7 C12 1.393(9) . ? C8 C9 1.370(13) . ? C8 H8 0.9500 . ? C9 C10 1.417(13) . ? C9 H9 0.9500 . ? C10 C11 1.377(13) . ? C10 H10 0.9500 . ? C11 C12 1.373(11) . ? C12 H12 0.9500 . ? C13 O6 1.237(9) . ? C13 N1 1.341(10) . ? C14 O3 1.183(10) . ? C14 N2 1.389(10) . ? C14 N1 1.407(9) . ? C15 O2 1.221(9) . ? C15 N2 1.336(10) . ? C16 N1 1.476(9) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 N2 1.478(9) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O4 1.421(10) . ? C18 C19 1.563(12) . ? C18 H18 1.0000 . ? C19 O5 1.431(11) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O4 1.377(12) . ? C20 O5 1.468(11) . ? C20 C21 1.535(13) . ? C20 C22 1.539(13) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 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 O1 C1 C2 121.5(8) . . ? O1 C1 C6 122.6(9) . . ? C2 C1 C6 115.9(7) . . ? C1 C2 C3 114.4(6) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C18 C3 C4 116.8(7) . . ? C18 C3 C2 110.4(6) . . ? C4 C3 C2 113.8(6) . . ? C18 C3 H3 104.9 . . ? C4 C3 H3 104.9 . . ? C2 C3 H3 104.9 . . ? C13 C4 C15 112.0(6) . . ? C13 C4 C3 109.1(6) . . ? C15 C4 C3 114.1(6) . . ? C13 C4 C5 105.7(5) . . ? C15 C4 C5 107.4(6) . . ? C3 C4 C5 108.2(6) . . ? C6 C5 C7 115.2(7) . . ? C6 C5 C4 112.9(6) . . ? C7 C5 C4 110.2(6) . . ? C6 C5 H5 105.9 . . ? C7 C5 H5 105.9 . . ? C4 C5 H5 105.9 . . ? C5 C6 C1 113.4(7) . . ? C5 C6 H6A 108.9 . . ? C1 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C1 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C12 120.0(7) . . ? C8 C7 C5 118.5(6) . . ? C12 C7 C5 121.4(6) . . ? C9 C8 C7 119.6(8) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 121.0(8) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C11 C10 C9 118.3(8) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C12 C11 C10 120.6(8) . . ? C12 C11 Br1 121.1(6) . . ? C10 C11 Br1 118.1(6) . . ? C11 C12 C7 120.3(7) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? O6 C13 N1 119.8(6) . . ? O6 C13 C4 119.3(7) . . ? N1 C13 C4 120.6(6) . . ? O3 C14 N2 122.9(7) . . ? O3 C14 N1 122.3(7) . . ? N2 C14 N1 114.8(6) . . ? O2 C15 N2 122.3(7) . . ? O2 C15 C4 118.6(7) . . ? N2 C15 C4 118.9(6) . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C18 C3 109.1(7) . . ? O4 C18 C19 102.6(6) . . ? C3 C18 C19 117.9(7) . . ? O4 C18 H18 109.0 . . ? C3 C18 H18 109.0 . . ? C19 C18 H18 109.0 . . ? O5 C19 C18 104.1(6) . . ? O5 C19 H19A 110.9 . . ? C18 C19 H19A 110.9 . . ? O5 C19 H19B 110.9 . . ? C18 C19 H19B 110.9 . . ? H19A C19 H19B 109.0 . . ? O4 C20 O5 102.5(7) . . ? O4 C20 C21 110.6(8) . . ? O5 C20 C21 106.0(7) . . ? O4 C20 C22 113.6(7) . . ? O5 C20 C22 111.3(8) . . ? C21 C20 C22 112.2(9) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C13 N1 C14 125.4(6) . . ? C13 N1 C16 120.0(6) . . ? C14 N1 C16 114.4(6) . . ? C15 N2 C14 127.0(6) . . ? C15 N2 C17 118.2(7) . . ? C14 N2 C17 114.8(6) . . ? C20 O4 C18 109.0(6) . . ? C19 O5 C20 105.4(7) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 65.05 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.939 _refine_diff_density_min -1.108 _refine_diff_density_rms 0.118