# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_bl46 _database_code_depnum_ccdc_archive 'CCDC 751391' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H23 N3 O4, H2 O' _chemical_formula_sum 'C13 H25 N3 O5' _chemical_formula_weight 303.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pca2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 10.1904(8) _cell_length_b 17.6150(12) _cell_length_c 9.4373(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1694.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 810 _cell_measurement_theta_min 3.16 _cell_measurement_theta_max 21.35 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9775 _exptl_absorpt_correction_T_max 0.9945 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker-AXS APEX- CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4537 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0862 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2321 _reflns_number_gt 1647 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT, (Bruker, 2004)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3(Farrugia,1997) _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0351P)^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 0.2(9) _refine_ls_number_reflns 2321 _refine_ls_number_parameters 215 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1011 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5822(3) 0.34268(17) 0.8414(3) 0.0522(9) Uani 1 1 d . A . O2 O 0.4936(3) 0.3811(2) 0.6315(3) 0.0659(11) Uani 1 1 d . . . O3 O 0.7074(2) 0.15686(14) 0.2663(2) 0.0247(6) Uani 1 1 d . . . O4 O 0.5174(2) 0.03007(15) 0.4118(3) 0.0356(7) Uani 1 1 d . . . N1 N 0.6231(3) 0.27632(19) 0.6487(3) 0.0314(9) Uani 1 1 d . . . H1 H 0.6723 0.2543 0.7105 0.038 Uiso 1 1 d R . . N2 N 0.4998(3) 0.18446(19) 0.2024(3) 0.0245(8) Uani 1 1 d . . . H2 H 0.5173 0.1705 0.1169 0.029 Uiso 1 1 d R . . N3 N 0.6184(3) 0.12375(18) 0.5366(3) 0.0201(7) Uani 1 1 d . . . H3 H 0.6785 0.1282 0.6134 0.024 Uiso 1 1 d R . . C1 C 0.4123(3) 0.1921(3) 0.4861(4) 0.0317(10) Uani 1 1 d . . . H1A H 0.3733 0.1406 0.4887 0.038 Uiso 1 1 calc R . . H1B H 0.3985 0.2159 0.5800 0.038 Uiso 1 1 calc R . . C2 C 0.3434(4) 0.2392(3) 0.3729(4) 0.0388(12) Uani 1 1 d . . . H2B H 0.2486 0.2429 0.3949 0.047 Uiso 1 1 calc R . . H2A H 0.3803 0.2912 0.3715 0.047 Uiso 1 1 calc R . . C3 C 0.3620(3) 0.2025(3) 0.2310(4) 0.0350(11) Uani 1 1 d . . . H3B H 0.3096 0.1552 0.2270 0.042 Uiso 1 1 calc R . . H3A H 0.3290 0.2371 0.1563 0.042 Uiso 1 1 calc R . . C4 C 0.5914(3) 0.1736(2) 0.2987(3) 0.0188(9) Uani 1 1 d . . . C5 C 0.5594(3) 0.1857(2) 0.4572(3) 0.0197(9) Uani 1 1 d . . . C6 C 0.5933(3) 0.0503(2) 0.5075(4) 0.0274(10) Uani 1 1 d . . . C7 C 0.6651(4) -0.0070(2) 0.5974(4) 0.0357(11) Uani 1 1 d . . . H7A H 0.6045 -0.0287 0.6671 0.054 Uiso 1 1 calc R . . H7C H 0.7379 0.0180 0.6467 0.054 Uiso 1 1 calc R . . H7B H 0.6996 -0.0475 0.5368 0.054 Uiso 1 1 calc R . . C8 C 0.6323(3) 0.2596(2) 0.4990(3) 0.0261(9) Uani 1 1 d . . . H8B H 0.7260 0.2547 0.4726 0.031 Uiso 1 1 calc R . . H8A H 0.5950 0.3025 0.4446 0.031 Uiso 1 1 calc R . . C9 C 0.5587(4) 0.3384(3) 0.7007(4) 0.0400(11) Uani 1 1 d . . . C10 C 0.5398(5) 0.4087(3) 0.9255(5) 0.0526(14) Uani 1 1 d . . . C11 C 0.394(2) 0.4249(19) 0.909(3) 0.075(7) Uani 0.52(4) 1 d P A 1 H11A H 0.3716 0.4267 0.8085 0.113 Uiso 0.52(4) 1 calc PR A 1 H11B H 0.3734 0.4738 0.9534 0.113 Uiso 0.52(4) 1 calc PR A 1 H11C H 0.3436 0.3847 0.9557 0.113 Uiso 0.52(4) 1 calc PR A 1 C12 C 0.618(3) 0.4045(17) 1.065(4) 0.054(5) Uani 0.52(4) 1 d P A 1 H12A H 0.6129 0.3530 1.1041 0.080 Uiso 0.52(4) 1 calc PR A 1 H12B H 0.5814 0.4406 1.1338 0.080 Uiso 0.52(4) 1 calc PR A 1 H12C H 0.7103 0.4174 1.0470 0.080 Uiso 0.52(4) 1 calc PR A 1 C11A C 0.396(2) 0.396(2) 0.959(3) 0.068(7) Uani 0.48(4) 1 d P A 2 H11D H 0.3429 0.4116 0.8777 0.102 Uiso 0.48(4) 1 calc PR A 2 H11E H 0.3719 0.4257 1.0422 0.102 Uiso 0.48(4) 1 calc PR A 2 H11F H 0.3816 0.3418 0.9779 0.102 Uiso 0.48(4) 1 calc PR A 2 C12A C 0.572(5) 0.382(2) 1.069(4) 0.088(11) Uani 0.48(4) 1 d P A 2 H12D H 0.5236 0.3353 1.0888 0.132 Uiso 0.48(4) 1 calc PR A 2 H12E H 0.5483 0.4211 1.1379 0.132 Uiso 0.48(4) 1 calc PR A 2 H12F H 0.6667 0.3720 1.0747 0.132 Uiso 0.48(4) 1 calc PR A 2 C13 C 0.5967(6) 0.4803(3) 0.8624(7) 0.097(2) Uani 1 1 d . A . H13A H 0.6904 0.4729 0.8437 0.145 Uiso 1 1 calc R . . H13B H 0.5851 0.5225 0.9290 0.145 Uiso 1 1 calc R . . H13C H 0.5514 0.4921 0.7734 0.145 Uiso 1 1 calc R . . O1W O 0.4475(2) -0.12578(15) 0.4240(3) 0.0355(7) Uani 1 1 d . . . H2W H 0.3620 -0.1251 0.3756 0.043 Uiso 1 1 d R . . H1W H 0.4866 -0.0749 0.4080 0.043 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.095(2) 0.034(2) 0.0275(15) -0.0112(16) -0.0122(16) 0.0305(18) O2 0.098(2) 0.055(2) 0.0449(18) -0.0098(19) -0.0278(19) 0.048(2) O3 0.0190(13) 0.0362(16) 0.0189(11) 0.0015(13) 0.0064(11) -0.0007(11) O4 0.0405(15) 0.0367(18) 0.0295(13) -0.0003(14) -0.0128(14) -0.0093(14) N1 0.0440(19) 0.027(2) 0.0227(16) -0.0020(17) -0.0124(15) 0.0148(18) N2 0.0256(16) 0.033(2) 0.0153(14) -0.0026(16) -0.0059(14) 0.0043(16) N3 0.0212(15) 0.025(2) 0.0141(14) -0.0011(15) -0.0050(12) -0.0012(16) C1 0.0221(19) 0.046(3) 0.027(2) -0.004(2) 0.0001(17) 0.0045(19) C2 0.028(2) 0.054(3) 0.035(2) -0.008(2) -0.0043(19) 0.009(2) C3 0.021(2) 0.051(3) 0.034(2) -0.003(2) -0.0052(19) 0.007(2) C4 0.022(2) 0.016(2) 0.0191(19) 0.0027(17) 0.0038(16) -0.0063(17) C5 0.0179(17) 0.026(2) 0.0151(17) -0.0006(17) -0.0030(15) 0.0009(18) C6 0.026(2) 0.038(3) 0.0180(18) 0.0021(19) 0.0029(18) -0.002(2) C7 0.044(2) 0.030(3) 0.033(2) 0.004(2) -0.0032(19) -0.002(2) C8 0.032(2) 0.025(3) 0.0212(18) -0.002(2) -0.0057(17) 0.0026(18) C9 0.055(3) 0.033(3) 0.031(2) -0.008(2) -0.012(2) 0.012(2) C10 0.080(3) 0.041(3) 0.037(3) -0.022(3) -0.008(3) 0.026(3) C11 0.090(11) 0.088(17) 0.048(11) -0.010(10) 0.011(9) 0.020(11) C12 0.082(11) 0.038(14) 0.041(8) -0.025(10) -0.026(8) 0.019(9) C11A 0.041(8) 0.12(2) 0.048(12) -0.014(12) 0.001(9) -0.002(11) C12A 0.17(4) 0.042(17) 0.051(9) -0.027(12) -0.01(2) 0.027(15) C13 0.157(6) 0.059(4) 0.075(4) -0.020(4) -0.004(4) -0.013(4) O1W 0.0382(13) 0.0414(19) 0.0269(14) 0.0073(15) -0.0076(13) -0.0109(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.352(5) . ? O1 C10 1.473(5) . ? O2 C9 1.197(5) . ? O3 C4 1.256(4) . ? O4 C6 1.241(4) . ? N1 C9 1.366(5) . ? N1 C8 1.447(5) . ? N2 C4 1.317(4) . ? N2 C3 1.465(4) . ? N3 C6 1.348(5) . ? N3 C5 1.453(4) . ? C1 C2 1.524(5) . ? C1 C5 1.528(4) . ? C2 C3 1.500(5) . ? C4 C5 1.545(4) . ? C5 C8 1.550(5) . ? C6 C7 1.507(5) . ? C10 C12A 1.47(4) . ? C10 C13 1.511(7) . ? C10 C11A 1.51(2) . ? C10 C11 1.52(3) . ? C10 C12 1.55(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 C9 O1 C10 121.4(4) . . ? C9 N1 C8 123.0(3) . . ? C4 N2 C3 125.7(3) . . ? C6 N3 C5 122.5(3) . . ? C2 C1 C5 111.5(3) . . ? C3 C2 C1 109.5(3) . . ? N2 C3 C2 112.3(3) . . ? O3 C4 N2 122.2(3) . . ? O3 C4 C5 117.8(3) . . ? N2 C4 C5 120.0(3) . . ? N3 C5 C1 111.7(3) . . ? N3 C5 C4 108.0(3) . . ? C1 C5 C4 112.9(3) . . ? N3 C5 C8 107.5(3) . . ? C1 C5 C8 111.3(3) . . ? C4 C5 C8 105.1(3) . . ? O4 C6 N3 122.8(4) . . ? O4 C6 C7 121.3(4) . . ? N3 C6 C7 115.8(3) . . ? N1 C8 C5 112.9(3) . . ? O2 C9 O1 126.8(4) . . ? O2 C9 N1 125.0(4) . . ? O1 C9 N1 108.2(4) . . ? C12A C10 O1 100.2(15) . . ? C12A C10 C13 122.9(18) . . ? O1 C10 C13 109.5(4) . . ? C12A C10 C11A 89(3) . . ? O1 C10 C11A 106.1(12) . . ? C13 C10 C11A 125.3(15) . . ? C12A C10 C11 112(3) . . ? O1 C10 C11 112.4(11) . . ? C13 C10 C11 100.3(13) . . ? C11A C10 C11 26.5(11) . . ? C12A C10 C12 23.3(18) . . ? O1 C10 C12 105.7(12) . . ? C13 C10 C12 100.3(11) . . ? C11A C10 C12 108.4(19) . . ? C11 C10 C12 126.9(17) . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.206 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.043 data_yl250406 _database_code_depnum_ccdc_archive 'CCDC 761459' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H31 N3 O8' _chemical_formula_weight 441.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 17.2196(7) _cell_length_b 27.2811(13) _cell_length_c 10.2859(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4832.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.1 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1888 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9618 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 'Stoe IPDS' _diffrn_measurement_method '\f oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 6 _diffrn_standards_decay_% ? _diffrn_reflns_number 43838 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.10 _reflns_number_total 5312 _reflns_number_gt 4011 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'X-RED (Stoe, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1022P)^2^+0.4575P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5312 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1686 _refine_ls_wR_factor_gt 0.1629 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.50866(10) 0.17413(5) 0.49198(16) 0.0387(4) Uani 1 1 d . . . C2 C 0.46202(11) 0.14387(6) 0.59239(19) 0.0458(4) Uani 1 1 d . A . C3 C 0.45334(10) 0.18956(6) 0.38192(18) 0.0412(4) Uani 1 1 d . . . C4 C 0.54170(11) 0.22098(6) 0.55576(16) 0.0416(4) Uani 1 1 d . . . H4A H 0.4994 0.2381 0.6026 0.050 Uiso 1 1 calc R . . H4B H 0.5816 0.2116 0.6204 0.050 Uiso 1 1 calc R . . C5 C 0.57758(11) 0.25590(6) 0.45727(16) 0.0425(4) Uani 1 1 d . . . H5A H 0.5389 0.2633 0.3888 0.051 Uiso 1 1 calc R . . H5B H 0.6226 0.2397 0.4154 0.051 Uiso 1 1 calc R . . C6 C 0.60440(11) 0.30386(6) 0.51999(17) 0.0418(4) Uani 1 1 d . . . H6A H 0.5612 0.3183 0.5705 0.050 Uiso 1 1 calc R . . H6B H 0.6478 0.2972 0.5805 0.050 Uiso 1 1 calc R . . C7 C 0.63078(11) 0.33995(6) 0.41614(17) 0.0415(4) Uani 1 1 d . . . H7A H 0.5878 0.3445 0.3533 0.050 Uiso 1 1 calc R . . H7B H 0.6750 0.3253 0.3683 0.050 Uiso 1 1 calc R . . C8 C 0.65591(10) 0.39101(6) 0.46719(15) 0.0370(3) Uani 1 1 d . . . C9 C 0.58894(10) 0.41150(6) 0.55048(16) 0.0399(4) Uani 1 1 d . . . C10 C 0.72510(11) 0.38554(6) 0.55273(17) 0.0428(4) Uani 1 1 d . . . C11 C 0.3980(2) 0.06617(13) 0.6179(4) 0.0567(8) Uani 0.80 1 d P A 1 H11A H 0.3617 0.0485 0.5598 0.068 Uiso 0.80 1 calc PR A 1 H11B H 0.3672 0.0845 0.6831 0.068 Uiso 0.80 1 calc PR A 1 C12 C 0.4508(2) 0.03050(13) 0.6844(4) 0.0776(9) Uani 0.80 1 d P A 1 H12A H 0.4811 0.0126 0.6191 0.116 Uiso 0.80 1 calc PR A 1 H12B H 0.4199 0.0073 0.7353 0.116 Uiso 0.80 1 calc PR A 1 H12C H 0.4862 0.0483 0.7423 0.116 Uiso 0.80 1 calc PR A 1 C12B C 0.4150(14) 0.0207(5) 0.6158(15) 0.095(5) Uani 0.20 1 d P A 2 H12D H 0.4009 0.0226 0.5237 0.114 Uiso 0.20 1 calc PR A 2 H12E H 0.3754 0.0020 0.6629 0.114 Uiso 0.20 1 calc PR A 2 H12F H 0.4654 0.0044 0.6248 0.114 Uiso 0.20 1 calc PR A 2 C11B C 0.4197(10) 0.0691(6) 0.6686(16) 0.067(4) Uani 0.20 1 d P A 2 H11C H 0.4590 0.0712 0.7387 0.081 Uiso 0.20 1 calc PR A 2 H11D H 0.3689 0.0803 0.7023 0.081 Uiso 0.20 1 calc PR A 2 C13 C 0.34322(12) 0.23830(8) 0.3344(3) 0.0659(6) Uani 1 1 d . . . H13A H 0.3115 0.2124 0.2927 0.079 Uiso 1 1 calc R . . H13B H 0.3727 0.2558 0.2661 0.079 Uiso 1 1 calc R . . C14 C 0.29249(16) 0.27311(11) 0.4072(4) 0.0944(9) Uani 1 1 d . . . H14A H 0.2639 0.2553 0.4746 0.142 Uiso 1 1 calc R . . H14B H 0.2556 0.2884 0.3470 0.142 Uiso 1 1 calc R . . H14C H 0.3246 0.2985 0.4477 0.142 Uiso 1 1 calc R . . C15 C 0.62074(10) 0.11971(6) 0.50467(17) 0.0427(4) Uani 1 1 d . . . C16 C 0.68063(14) 0.09035(9) 0.4327(2) 0.0642(6) Uani 1 1 d . . . H16A H 0.7088 0.1118 0.3724 0.096 Uiso 1 1 calc R . . H16B H 0.6550 0.0641 0.3837 0.096 Uiso 1 1 calc R . . H16C H 0.7172 0.0760 0.4949 0.096 Uiso 1 1 calc R . . C17 C 0.45892(12) 0.44027(9) 0.5360(3) 0.0668(6) Uani 1 1 d . . . H17A H 0.4348 0.4686 0.4915 0.080 Uiso 1 1 calc R . . H17B H 0.4675 0.4492 0.6282 0.080 Uiso 1 1 calc R . . C18 C 0.40626(13) 0.39709(9) 0.5281(3) 0.0683(6) Uani 1 1 d . . . H18A H 0.4006 0.3871 0.4371 0.102 Uiso 1 1 calc R . . H18B H 0.3553 0.4058 0.5635 0.102 Uiso 1 1 calc R . . H18C H 0.4283 0.3700 0.5785 0.102 Uiso 1 1 calc R . . C19 C 0.68923(10) 0.46989(6) 0.37222(17) 0.0409(4) Uani 1 1 d . . . C20 C 0.69897(14) 0.49871(7) 0.2487(2) 0.0578(5) Uani 1 1 d . . . H20A H 0.6861 0.5332 0.2649 0.087 Uiso 1 1 calc R . . H20B H 0.6642 0.4855 0.1818 0.087 Uiso 1 1 calc R . . H20C H 0.7529 0.4962 0.2190 0.087 Uiso 1 1 calc R . . N1 N 0.56945(8) 0.14450(5) 0.43240(13) 0.0378(3) Uani 1 1 d . . . H1 H 0.5725 0.1429 0.3471 0.045 Uiso 1 1 calc R . . N2 N 0.67401(9) 0.42154(5) 0.35599(13) 0.0405(3) Uani 1 1 d . . . H2 H 0.6751 0.4086 0.2776 0.049 Uiso 1 1 calc R . . N3 N 0.77803(11) 0.37914(6) 0.61670(19) 0.0600(4) Uani 1 1 d . . . O1 O 0.44222(10) 0.15891(5) 0.69601(15) 0.0646(4) Uani 1 1 d . . . O2 O 0.44563(8) 0.09979(5) 0.54298(15) 0.0558(4) Uani 1 1 d . . . O3 O 0.46354(8) 0.18012(5) 0.26986(13) 0.0520(3) Uani 1 1 d . . . O4 O 0.39620(8) 0.21685(5) 0.42932(14) 0.0515(3) Uani 1 1 d . . . O5 O 0.61890(9) 0.12144(5) 0.62404(12) 0.0533(4) Uani 1 1 d . . . O6 O 0.58666(9) 0.40843(5) 0.66627(13) 0.0532(3) Uani 1 1 d . . . O7 O 0.53340(7) 0.42847(5) 0.47445(14) 0.0516(3) Uani 1 1 d . . . O8 O 0.69422(8) 0.48798(4) 0.48081(12) 0.0473(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0466(9) 0.0324(7) 0.0372(8) 0.0035(6) 0.0035(7) 0.0020(6) C2 0.0492(10) 0.0405(8) 0.0478(10) 0.0082(7) 0.0065(8) 0.0049(7) C3 0.0426(9) 0.0336(7) 0.0472(10) 0.0066(7) 0.0016(7) -0.0038(6) C4 0.0557(10) 0.0333(7) 0.0359(8) -0.0016(6) 0.0025(7) 0.0009(7) C5 0.0540(10) 0.0345(8) 0.0390(8) -0.0027(6) 0.0025(7) -0.0040(7) C6 0.0549(10) 0.0329(8) 0.0375(8) -0.0013(6) 0.0005(7) -0.0022(7) C7 0.0531(10) 0.0341(8) 0.0374(8) -0.0025(6) 0.0015(7) -0.0035(7) C8 0.0439(8) 0.0327(7) 0.0343(8) -0.0012(6) -0.0010(7) -0.0018(6) C9 0.0484(9) 0.0314(7) 0.0399(9) -0.0021(6) 0.0014(7) -0.0043(6) C10 0.0491(9) 0.0352(8) 0.0441(9) -0.0005(6) -0.0007(8) 0.0006(7) C11 0.060(2) 0.0469(15) 0.063(2) 0.0167(16) -0.0017(16) -0.0113(13) C12 0.091(2) 0.0629(18) 0.079(2) 0.0267(18) -0.0176(19) -0.0181(16) C12B 0.162(17) 0.062(8) 0.061(8) -0.003(6) 0.002(10) -0.035(9) C11B 0.069(10) 0.072(9) 0.061(10) 0.047(8) -0.011(6) -0.021(7) C13 0.0477(11) 0.0568(12) 0.0933(17) 0.0234(11) -0.0061(11) 0.0045(9) C14 0.0609(15) 0.0701(15) 0.152(3) 0.0020(18) -0.0078(17) 0.0195(12) C15 0.0492(9) 0.0393(8) 0.0396(9) 0.0011(7) -0.0008(7) 0.0024(7) C16 0.0643(13) 0.0772(14) 0.0511(11) -0.0012(10) -0.0001(10) 0.0288(11) C17 0.0472(11) 0.0654(13) 0.0878(16) -0.0141(12) 0.0043(11) 0.0078(9) C18 0.0527(12) 0.0674(13) 0.0848(16) 0.0107(12) 0.0038(11) 0.0005(10) C19 0.0423(9) 0.0386(8) 0.0419(9) 0.0002(7) -0.0020(7) -0.0058(7) C20 0.0790(14) 0.0472(9) 0.0473(11) 0.0040(8) 0.0005(10) -0.0162(9) N1 0.0450(7) 0.0346(6) 0.0338(7) 0.0006(5) 0.0028(6) 0.0026(5) N2 0.0523(8) 0.0369(7) 0.0324(7) -0.0014(5) 0.0007(6) -0.0056(6) N3 0.0587(10) 0.0542(9) 0.0672(11) 0.0001(8) -0.0153(9) 0.0051(7) O1 0.0861(10) 0.0530(8) 0.0547(8) 0.0081(7) 0.0296(8) 0.0024(7) O2 0.0616(8) 0.0381(6) 0.0675(9) 0.0082(6) 0.0118(7) -0.0069(6) O3 0.0545(8) 0.0579(7) 0.0435(7) 0.0059(6) -0.0049(6) 0.0032(6) O4 0.0467(7) 0.0439(6) 0.0640(8) 0.0064(6) 0.0015(6) 0.0054(5) O5 0.0704(9) 0.0541(7) 0.0354(7) 0.0032(5) -0.0037(6) 0.0156(6) O6 0.0692(9) 0.0498(7) 0.0406(7) -0.0031(5) 0.0095(6) -0.0001(6) O7 0.0448(7) 0.0519(7) 0.0581(8) -0.0013(6) -0.0011(6) 0.0050(5) O8 0.0614(8) 0.0385(6) 0.0422(7) -0.0031(5) -0.0036(6) -0.0060(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.458(2) . ? C1 C3 1.538(2) . ? C1 C4 1.545(2) . ? C1 C2 1.547(2) . ? C2 O1 1.192(2) . ? C2 O2 1.335(2) . ? C3 O3 1.194(2) . ? C3 O4 1.327(2) . ? C4 C5 1.522(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.530(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.522(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.550(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N2 1.449(2) . ? C8 C10 1.489(2) . ? C8 C9 1.542(2) . ? C9 O6 1.195(2) . ? C9 O7 1.319(2) . ? C10 N3 1.138(2) . ? C11 O2 1.452(4) . ? C11 C12 1.498(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C12B C11B 1.43(2) . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C11B O2 1.603(14) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C13 O4 1.459(3) . ? C13 C14 1.492(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O5 1.229(2) . ? C15 N1 1.338(2) . ? C15 C16 1.501(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 O7 1.466(3) . ? C17 C18 1.489(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 O8 1.224(2) . ? C19 N2 1.355(2) . ? C19 C20 1.503(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? 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 N1 C1 C3 106.68(13) . . ? N1 C1 C4 111.89(14) . . ? C3 C1 C4 108.31(13) . . ? N1 C1 C2 110.95(12) . . ? C3 C1 C2 108.41(14) . . ? C4 C1 C2 110.43(14) . . ? O1 C2 O2 126.15(17) . . ? O1 C2 C1 124.17(16) . . ? O2 C2 C1 109.64(15) . . ? O3 C3 O4 125.80(17) . . ? O3 C3 C1 124.07(16) . . ? O4 C3 C1 110.02(15) . . ? C5 C4 C1 112.62(13) . . ? C5 C4 H4A 109.1 . . ? C1 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C1 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C4 C5 C6 112.16(14) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 110.32(14) . . ? C7 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? C7 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C6 C7 C8 115.26(14) . . ? C6 C7 H7A 108.5 . . ? C8 C7 H7A 108.5 . . ? C6 C7 H7B 108.5 . . ? C8 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? N2 C8 C10 110.61(14) . . ? N2 C8 C9 113.03(13) . . ? C10 C8 C9 107.85(13) . . ? N2 C8 C7 108.01(13) . . ? C10 C8 C7 109.49(13) . . ? C9 C8 C7 107.77(13) . . ? O6 C9 O7 126.28(17) . . ? O6 C9 C8 123.59(16) . . ? O7 C9 C8 109.89(14) . . ? N3 C10 C8 176.86(18) . . ? O2 C11 C12 108.1(3) . . ? O2 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? O2 C11 H11B 110.1 . . ? C12 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? C11B C12B H12D 109.5 . . ? C11B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C11B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? C12B C11B O2 101.1(13) . . ? C12B C11B H11C 111.6 . . ? O2 C11B H11C 111.6 . . ? C12B C11B H11D 111.6 . . ? O2 C11B H11D 111.6 . . ? H11C C11B H11D 109.4 . . ? O4 C13 C14 106.6(2) . . ? O4 C13 H13A 110.4 . . ? C14 C13 H13A 110.4 . . ? O4 C13 H13B 110.4 . . ? C14 C13 H13B 110.4 . . ? H13A C13 H13B 108.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O5 C15 N1 121.23(16) . . ? O5 C15 C16 122.07(16) . . ? N1 C15 C16 116.69(16) . . ? 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 . . ? O7 C17 C18 109.58(18) . . ? O7 C17 H17A 109.8 . . ? C18 C17 H17A 109.8 . . ? O7 C17 H17B 109.8 . . ? C18 C17 H17B 109.8 . . ? H17A C17 H17B 108.2 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O8 C19 N2 121.22(15) . . ? O8 C19 C20 123.53(15) . . ? N2 C19 C20 115.25(15) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C15 N1 C1 121.39(13) . . ? C15 N1 H1 119.3 . . ? C1 N1 H1 119.3 . . ? C19 N2 C8 120.26(13) . . ? C19 N2 H2 119.9 . . ? C8 N2 H2 119.9 . . ? C2 O2 C11 119.1(2) . . ? C2 O2 C11B 102.8(7) . . ? C11 O2 C11B 23.8(5) . . ? C3 O4 C13 116.29(16) . . ? C9 O7 C17 117.07(17) . . ? 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 N1 C1 C2 O1 137.70(19) . . . . ? C3 C1 C2 O1 -105.5(2) . . . . ? C4 C1 C2 O1 13.0(3) . . . . ? N1 C1 C2 O2 -44.46(19) . . . . ? C3 C1 C2 O2 72.37(17) . . . . ? C4 C1 C2 O2 -169.12(15) . . . . ? N1 C1 C3 O3 -3.5(2) . . . . ? C4 C1 C3 O3 117.09(18) . . . . ? C2 C1 C3 O3 -123.07(18) . . . . ? N1 C1 C3 O4 -179.96(13) . . . . ? C4 C1 C3 O4 -59.35(17) . . . . ? C2 C1 C3 O4 60.50(17) . . . . ? N1 C1 C4 C5 64.58(18) . . . . ? C3 C1 C4 C5 -52.74(19) . . . . ? C2 C1 C4 C5 -171.31(14) . . . . ? C1 C4 C5 C6 175.56(15) . . . . ? C4 C5 C6 C7 -173.19(15) . . . . ? C5 C6 C7 C8 177.34(15) . . . . ? C6 C7 C8 N2 -176.19(15) . . . . ? C6 C7 C8 C10 63.29(19) . . . . ? C6 C7 C8 C9 -53.76(19) . . . . ? N2 C8 C9 O6 -143.72(16) . . . . ? C10 C8 C9 O6 -21.1(2) . . . . ? C7 C8 C9 O6 97.00(18) . . . . ? N2 C8 C9 O7 41.64(18) . . . . ? C10 C8 C9 O7 164.24(13) . . . . ? C7 C8 C9 O7 -77.64(16) . . . . ? N2 C8 C10 N3 -114(4) . . . . ? C9 C8 C10 N3 122(4) . . . . ? C7 C8 C10 N3 5(4) . . . . ? O5 C15 N1 C1 -0.7(3) . . . . ? C16 C15 N1 C1 179.87(17) . . . . ? C3 C1 N1 C15 -170.49(14) . . . . ? C4 C1 N1 C15 71.22(18) . . . . ? C2 C1 N1 C15 -52.6(2) . . . . ? O8 C19 N2 C8 5.9(3) . . . . ? C20 C19 N2 C8 -173.90(16) . . . . ? C10 C8 N2 C19 -67.65(19) . . . . ? C9 C8 N2 C19 53.4(2) . . . . ? C7 C8 N2 C19 172.54(15) . . . . ? O1 C2 O2 C11 1.4(3) . . . . ? C1 C2 O2 C11 -176.4(2) . . . . ? O1 C2 O2 C11B -17.3(7) . . . . ? C1 C2 O2 C11B 164.9(7) . . . . ? C12 C11 O2 C2 -99.2(3) . . . . ? C12 C11 O2 C11B -48(2) . . . . ? C12B C11B O2 C2 -171.0(12) . . . . ? C12B C11B O2 C11 52.9(18) . . . . ? O3 C3 O4 C13 -2.2(3) . . . . ? C1 C3 O4 C13 174.15(14) . . . . ? C14 C13 O4 C3 -171.35(18) . . . . ? O6 C9 O7 C17 -6.4(3) . . . . ? C8 C9 O7 C17 168.08(14) . . . . ? C18 C17 O7 C9 -93.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.327 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.051 data_yl200406 _database_code_depnum_ccdc_archive 'CCDC 761460' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H22 Br N O5' _chemical_formula_weight 352.23 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 monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.996(3) _cell_length_b 10.0702(11) _cell_length_c 9.3258(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.477(13) _cell_angle_gamma 90.00 _cell_volume 1682.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 4286 _cell_measurement_theta_min 4.93 _cell_measurement_theta_max 128.06 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 3.489 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4310 _exptl_absorpt_correction_T_max 0.9321 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS 2T' _diffrn_measurement_method '\o oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 7.5 _diffrn_standards_decay_% ? _diffrn_reflns_number 10736 _diffrn_reflns_av_R_equivalents 0.0855 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 58.91 _reflns_number_total 2353 _reflns_number_gt 1867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe, 2005)' _computing_cell_refinement 'X-Area (Stoe, 2005)' _computing_data_reduction 'X-RED32 (Stoe, 2005)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1249P)^2^+1.8738P] 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 0.019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2353 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.2413 _refine_ls_wR_factor_gt 0.2050 _refine_ls_goodness_of_fit_ref 1.215 _refine_ls_restrained_S_all 1.215 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2860(3) 0.4234(5) 0.9058(5) 0.0485(12) Uani 1 1 d . . . C2 C 0.3336(3) 0.5147(5) 0.8193(6) 0.0497(13) Uani 1 1 d . . . C3 C 0.2579(3) 0.5067(6) 1.0291(6) 0.0507(13) Uani 1 1 d . . . C4 C 0.2179(3) 0.3731(6) 0.8076(5) 0.0508(13) Uani 1 1 d . . . H4A H 0.1918 0.4503 0.7603 0.061 Uiso 1 1 calc R . . H4B H 0.2358 0.3165 0.7312 0.061 Uiso 1 1 calc R . . C5 C 0.1625(3) 0.2940(6) 0.8875(5) 0.0560(14) Uani 1 1 d . . . H5A H 0.1335 0.3554 0.9435 0.067 Uiso 1 1 calc R . . H5B H 0.1900 0.2322 0.9560 0.067 Uiso 1 1 calc R . . C6 C 0.1090(3) 0.2149(6) 0.7819(5) 0.0569(14) Uani 1 1 d . . . H6A H 0.0857 0.2758 0.7073 0.068 Uiso 1 1 calc R . . H6B H 0.1377 0.1474 0.7332 0.068 Uiso 1 1 calc R . . C7 C 0.0489(4) 0.1471(7) 0.8555(7) 0.0756(18) Uani 1 1 d . . . H7A H 0.0184 0.2145 0.9004 0.091 Uiso 1 1 calc R . . H7B H 0.0719 0.0886 0.9327 0.091 Uiso 1 1 calc R . . C11 C 0.4491(3) 0.6303(6) 0.8275(8) 0.0721(17) Uani 1 1 d . . . H11A H 0.4506 0.6022 0.7261 0.087 Uiso 1 1 calc R . . H11B H 0.5000 0.6211 0.8769 0.087 Uiso 1 1 calc R . . C12 C 0.4251(4) 0.7725(7) 0.8318(10) 0.089(2) Uani 1 1 d . . . H12C H 0.4203 0.7985 0.9317 0.107 Uiso 1 1 calc R . . H12B H 0.3769 0.7832 0.7747 0.107 Uiso 1 1 calc R . . H12A H 0.4625 0.8287 0.7917 0.107 Uiso 1 1 calc R . . C13 C 0.1924(3) 0.7036(6) 1.0784(6) 0.0691(17) Uani 1 1 d . . . H13A H 0.2302 0.7305 1.1572 0.083 Uiso 1 1 calc R . . H13B H 0.1515 0.6567 1.1210 0.083 Uiso 1 1 calc R . . C14 C 0.1629(4) 0.8226(7) 0.9961(7) 0.083(2) Uani 1 1 d . . . H14C H 0.1280 0.7942 0.9147 0.100 Uiso 1 1 calc R . . H14B H 0.2044 0.8715 0.9601 0.100 Uiso 1 1 calc R . . H14A H 0.1368 0.8803 1.0595 0.100 Uiso 1 1 calc R . . C15 C 0.3691(3) 0.2366(5) 0.8869(5) 0.0501(13) Uani 1 1 d . . . C16 C 0.4025(3) 0.1136(6) 0.9546(6) 0.0619(15) Uani 1 1 d . . . H16A H 0.3724 0.0367 0.9209 0.074 Uiso 1 1 calc R . . H16B H 0.4036 0.1205 1.0596 0.074 Uiso 1 1 calc R . . H16C H 0.4535 0.1029 0.9277 0.074 Uiso 1 1 calc R . . N1 N 0.3293(2) 0.3140(4) 0.9697(4) 0.0469(10) Uani 1 1 d . . . H1A H 0.3298 0.2979 1.0625 0.056 Uiso 1 1 calc R . . O1 O 0.3151(2) 0.5573(4) 0.7017(4) 0.0561(10) Uani 1 1 d . . . O2 O 0.3976(2) 0.5440(3) 0.8977(4) 0.0584(11) Uani 1 1 d . . . O3 O 0.2625(2) 0.4721(4) 1.1527(4) 0.0614(11) Uani 1 1 d . . . O4 O 0.2262(2) 0.6168(4) 0.9760(4) 0.0594(10) Uani 1 1 d . . . O5 O 0.3757(2) 0.2655(4) 0.7599(3) 0.0543(10) Uani 1 1 d . . . Br1 Br -0.01458(5) 0.04275(9) 0.71918(10) 0.1022(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.051(3) 0.054(3) 0.042(2) -0.002(2) 0.008(2) -0.001(2) C2 0.054(3) 0.045(3) 0.051(3) -0.003(2) 0.010(2) -0.002(2) C3 0.047(3) 0.052(3) 0.053(3) -0.006(3) 0.009(2) -0.001(2) C4 0.050(3) 0.058(3) 0.044(3) 0.000(2) 0.003(2) -0.006(2) C5 0.052(3) 0.065(4) 0.052(3) 0.002(3) 0.008(2) -0.005(3) C6 0.057(3) 0.059(4) 0.054(3) -0.009(2) 0.004(2) -0.006(3) C7 0.068(4) 0.083(5) 0.077(4) 0.001(3) 0.017(3) -0.011(3) C11 0.062(3) 0.068(4) 0.089(4) 0.003(3) 0.022(3) -0.013(3) C12 0.083(5) 0.061(4) 0.124(6) -0.002(4) 0.014(4) -0.016(3) C13 0.071(4) 0.070(4) 0.068(3) -0.022(3) 0.012(3) 0.010(3) C14 0.094(5) 0.072(4) 0.083(4) -0.012(4) -0.002(4) 0.021(4) C15 0.049(3) 0.059(3) 0.042(3) -0.005(2) 0.006(2) -0.006(2) C16 0.073(4) 0.061(4) 0.053(3) 0.005(3) 0.014(3) 0.016(3) N1 0.050(2) 0.052(2) 0.0383(19) 0.0009(18) 0.0051(16) 0.0048(19) O1 0.060(2) 0.061(2) 0.048(2) 0.0082(16) 0.0070(16) -0.0026(17) O2 0.053(2) 0.063(3) 0.059(2) -0.0023(17) 0.0081(17) -0.0104(17) O3 0.071(3) 0.073(3) 0.041(2) -0.0028(17) 0.0111(17) 0.0080(19) O4 0.063(2) 0.061(2) 0.055(2) -0.0054(18) 0.0106(16) 0.0107(19) O5 0.065(2) 0.058(2) 0.0409(19) -0.0015(15) 0.0105(15) -0.0018(17) Br1 0.0836(8) 0.1028(9) 0.1186(10) -0.0228(5) 0.0016(5) -0.0354(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.445(7) . ? C1 C2 1.537(7) . ? C1 C4 1.543(7) . ? C1 C3 1.546(7) . ? C2 O1 1.194(6) . ? C2 O2 1.337(7) . ? C3 O3 1.200(6) . ? C3 O4 1.321(7) . ? C4 C5 1.526(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.532(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.500(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 Br1 1.936(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C11 O2 1.469(6) . ? C11 C12 1.497(10) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12C 0.9800 . ? C12 H12B 0.9800 . ? C12 H12A 0.9800 . ? C13 O4 1.469(6) . ? C13 C14 1.493(9) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14C 0.9800 . ? C14 H14B 0.9800 . ? C14 H14A 0.9800 . ? C15 O5 1.236(6) . ? C15 N1 1.349(6) . ? C15 C16 1.490(8) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1 H1A 0.8800 . ? 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 N1 C1 C2 111.5(4) . . ? N1 C1 C4 111.2(4) . . ? C2 C1 C4 109.6(4) . . ? N1 C1 C3 108.0(4) . . ? C2 C1 C3 107.7(4) . . ? C4 C1 C3 108.8(4) . . ? O1 C2 O2 125.0(5) . . ? O1 C2 C1 125.2(5) . . ? O2 C2 C1 109.8(4) . . ? O3 C3 O4 126.2(5) . . ? O3 C3 C1 124.1(5) . . ? O4 C3 C1 109.7(4) . . ? C5 C4 C1 113.6(4) . . ? C5 C4 H4A 108.8 . . ? C1 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C1 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 110.9(4) . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 112.3(4) . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C6 C7 Br1 110.7(4) . . ? C6 C7 H7A 109.5 . . ? Br1 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? Br1 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? O2 C11 C12 111.0(5) . . ? O2 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? O2 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 H12C 109.5 . . ? C11 C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? C11 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? H12B C12 H12A 109.5 . . ? O4 C13 C14 107.0(5) . . ? O4 C13 H13A 110.3 . . ? C14 C13 H13A 110.3 . . ? O4 C13 H13B 110.3 . . ? C14 C13 H13B 110.3 . . ? H13A C13 H13B 108.6 . . ? C13 C14 H14C 109.5 . . ? C13 C14 H14B 109.5 . . ? H14C C14 H14B 109.5 . . ? C13 C14 H14A 109.5 . . ? H14C C14 H14A 109.5 . . ? H14B C14 H14A 109.5 . . ? O5 C15 N1 121.1(5) . . ? O5 C15 C16 122.0(5) . . ? N1 C15 C16 116.9(4) . . ? 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 N1 C1 120.0(4) . . ? C15 N1 H1A 120.0 . . ? C1 N1 H1A 120.0 . . ? C2 O2 C11 115.7(4) . . ? C3 O4 C13 116.5(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 O1 134.5(5) . . . . ? C4 C1 C2 O1 11.0(7) . . . . ? C3 C1 C2 O1 -107.2(6) . . . . ? N1 C1 C2 O2 -48.2(5) . . . . ? C4 C1 C2 O2 -171.6(4) . . . . ? C3 C1 C2 O2 70.2(5) . . . . ? N1 C1 C3 O3 -10.4(7) . . . . ? C2 C1 C3 O3 -130.9(5) . . . . ? C4 C1 C3 O3 110.4(6) . . . . ? N1 C1 C3 O4 172.0(4) . . . . ? C2 C1 C3 O4 51.5(5) . . . . ? C4 C1 C3 O4 -67.2(5) . . . . ? N1 C1 C4 C5 62.7(5) . . . . ? C2 C1 C4 C5 -173.6(4) . . . . ? C3 C1 C4 C5 -56.1(6) . . . . ? C1 C4 C5 C6 -164.1(5) . . . . ? C4 C5 C6 C7 -174.1(5) . . . . ? C5 C6 C7 Br1 -177.6(4) . . . . ? O5 C15 N1 C1 7.7(7) . . . . ? C16 C15 N1 C1 -170.6(5) . . . . ? C2 C1 N1 C15 -52.5(6) . . . . ? C4 C1 N1 C15 70.1(5) . . . . ? C3 C1 N1 C15 -170.7(4) . . . . ? O1 C2 O2 C11 -3.1(8) . . . . ? C1 C2 O2 C11 179.6(4) . . . . ? C12 C11 O2 C2 78.7(7) . . . . ? O3 C3 O4 C13 -1.1(8) . . . . ? C1 C3 O4 C13 176.4(4) . . . . ? C14 C13 O4 C3 178.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 58.91 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.467 _refine_diff_density_min -0.670 _refine_diff_density_rms 0.090 data_yl040506 _database_code_depnum_ccdc_archive 'CCDC 761461' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H43 N3 O10' _chemical_formula_weight 545.62 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 8.8810(11) _cell_length_b 20.9682(19) _cell_length_c 16.241(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.327(10) _cell_angle_gamma 90.00 _cell_volume 2965.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 25349 _cell_measurement_theta_min 4.21 _cell_measurement_theta_max 129.68 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 0.787 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8557 _exptl_absorpt_correction_T_max 0.9372 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS 2T' _diffrn_measurement_method '\o oscillation scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 50-200 _diffrn_standards_interval_count 'every image' _diffrn_standards_interval_time 7.5 _diffrn_standards_decay_% ? _diffrn_reflns_number 30674 _diffrn_reflns_av_R_equivalents 0.0957 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 58.99 _reflns_number_total 4152 _reflns_number_gt 2962 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area (Stoe, 2005)' _computing_cell_refinement 'X-Area (Stoe, 2005)' _computing_data_reduction 'X-RED32 (Stoe, 2005)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1159P)^2^+2.1814P] 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 0.0049(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4152 _refine_ls_number_parameters 362 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.2198 _refine_ls_wR_factor_gt 0.1751 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6446(4) 0.35310(16) 0.1300(2) 0.0378(9) Uani 1 1 d . . . C2 C 0.5311(4) 0.35810(17) 0.0465(2) 0.0397(9) Uani 1 1 d . . . C3 C 0.7915(4) 0.38804(19) 0.1162(3) 0.0450(10) Uani 1 1 d . . . C4 C 0.5878(4) 0.38516(17) 0.2031(2) 0.0419(9) Uani 1 1 d . . . H4A H 0.6651 0.3783 0.2552 0.050 Uiso 1 1 calc R . . H4B H 0.5803 0.4317 0.1926 0.050 Uiso 1 1 calc R . . C5 C 0.4328(4) 0.36119(19) 0.2171(2) 0.0438(9) Uani 1 1 d . . . H5A H 0.4253 0.3147 0.2061 0.053 Uiso 1 1 calc R . . H5B H 0.3500 0.3824 0.1767 0.053 Uiso 1 1 calc R . . C6 C 0.4096(4) 0.37410(18) 0.3062(2) 0.0442(9) Uani 1 1 d . . . H6A H 0.4849 0.3488 0.3464 0.053 Uiso 1 1 calc R . . H6B H 0.4289 0.4198 0.3196 0.053 Uiso 1 1 calc R . . C7 C 0.2481(4) 0.35700(19) 0.3167(2) 0.0430(9) Uani 1 1 d . . . H7A H 0.2140 0.3192 0.2814 0.052 Uiso 1 1 calc R . . H7B H 0.1790 0.3927 0.2945 0.052 Uiso 1 1 calc R . . C8 C 0.2271(4) 0.34250(17) 0.4073(2) 0.0399(9) Uani 1 1 d . . . C9 C 0.2903(4) 0.39813(19) 0.4649(2) 0.0463(10) Uani 1 1 d . . . C10 C 0.3144(4) 0.28182(18) 0.4424(3) 0.0474(10) Uani 1 1 d . . . H10A H 0.4249 0.2873 0.4419 0.057 Uiso 1 1 calc R . . H10B H 0.3038 0.2757 0.5015 0.057 Uiso 1 1 calc R . . C11 C 0.3744(5) 0.4287(2) -0.0489(3) 0.0588(12) Uani 1 1 d . . . H11A H 0.3140 0.4678 -0.0449 0.071 Uiso 1 1 calc R . . H11B H 0.3019 0.3925 -0.0609 0.071 Uiso 1 1 calc R . . C12 C 0.4587(6) 0.4357(2) -0.1192(3) 0.0631(12) Uani 1 1 d . . . H12A H 0.5348 0.4699 -0.1061 0.095 Uiso 1 1 calc R . . H12B H 0.3858 0.4462 -0.1710 0.095 Uiso 1 1 calc R . . H12C H 0.5108 0.3955 -0.1269 0.095 Uiso 1 1 calc R . . C13 C 1.0128(5) 0.3778(3) 0.0556(4) 0.0823(16) Uani 1 1 d D . . H13A H 1.0601 0.4054 0.1032 0.099 Uiso 1 1 calc R A 1 H13B H 1.0016 0.4026 0.0029 0.099 Uiso 1 1 calc R A 1 C14 C 1.1114(7) 0.3167(4) 0.0516(5) 0.078(2) Uani 0.70 1 d P B 1 H14A H 1.1087 0.2899 0.1007 0.117 Uiso 0.70 1 calc PR B 1 H14B H 1.2177 0.3290 0.0513 0.117 Uiso 0.70 1 calc PR B 1 H14C H 1.0696 0.2928 0.0003 0.117 Uiso 0.70 1 calc PR B 1 C14B C 0.966(2) 0.4439(8) -0.0006(12) 0.091(6) Uani 0.30 1 d PD B 2 H14D H 1.0594 0.4653 -0.0095 0.136 Uiso 0.30 1 calc PR B 2 H14E H 0.9084 0.4725 0.0296 0.136 Uiso 0.30 1 calc PR B 2 H14F H 0.9020 0.4327 -0.0550 0.136 Uiso 0.30 1 calc PR B 2 C15 C 0.7975(4) 0.2659(2) 0.2019(2) 0.0484(10) Uani 1 1 d . . . C16 C 0.8201(5) 0.1960(2) 0.2138(3) 0.0665(13) Uani 1 1 d . . . H16C H 0.9293 0.1858 0.2192 0.080 Uiso 1 1 calc R . . H16B H 0.7606 0.1735 0.1654 0.080 Uiso 1 1 calc R . . H16A H 0.7854 0.1828 0.2649 0.080 Uiso 1 1 calc R . . C17 C 0.2434(6) 0.50229(19) 0.5115(3) 0.0642(13) Uani 1 1 d . . . H17A H 0.1866 0.5408 0.4874 0.077 Uiso 1 1 calc R . . H17B H 0.3542 0.5100 0.5142 0.077 Uiso 1 1 calc R . . C18 C 0.2152(6) 0.4910(2) 0.5978(3) 0.0769(15) Uani 1 1 d . . . H18A H 0.1084 0.4778 0.5945 0.115 Uiso 1 1 calc R . . H18B H 0.2346 0.5304 0.6306 0.115 Uiso 1 1 calc R . . H18C H 0.2841 0.4574 0.6250 0.115 Uiso 1 1 calc R . . C19 C -0.0039(4) 0.32790(17) 0.4692(2) 0.0407(9) Uani 1 1 d . . . C20 C -0.1740(4) 0.31629(19) 0.4510(2) 0.0460(10) Uani 1 1 d . . . H20A H -0.1995 0.2848 0.4907 0.069 Uiso 1 1 calc R . . H20B H -0.2057 0.3001 0.3936 0.069 Uiso 1 1 calc R . . H20C H -0.2278 0.3563 0.4568 0.069 Uiso 1 1 calc R . . C21 C 0.3402(5) 0.19514(19) 0.3436(3) 0.0502(10) Uani 1 1 d . . . C22 C 0.3211(6) 0.1049(2) 0.2467(3) 0.0676(13) Uani 1 1 d . . . C23 C 0.2000(8) 0.0528(3) 0.2256(4) 0.105(2) Uani 1 1 d . . . H23A H 0.1972 0.0275 0.2759 0.157 Uiso 1 1 calc R . . H23B H 0.2256 0.0252 0.1817 0.157 Uiso 1 1 calc R . . H23C H 0.0993 0.0724 0.2056 0.157 Uiso 1 1 calc R . . C24 C 0.4785(8) 0.0778(3) 0.2817(5) 0.118(2) Uani 1 1 d . . . H24A H 0.5531 0.1126 0.2935 0.177 Uiso 1 1 calc R . . H24B H 0.5086 0.0487 0.2405 0.177 Uiso 1 1 calc R . . H24C H 0.4757 0.0544 0.3336 0.177 Uiso 1 1 calc R . . C25 C 0.3219(8) 0.1460(3) 0.1713(4) 0.0964(19) Uani 1 1 d . . . H25A H 0.2188 0.1633 0.1510 0.145 Uiso 1 1 calc R . . H25B H 0.3525 0.1203 0.1268 0.145 Uiso 1 1 calc R . . H25C H 0.3948 0.1811 0.1866 0.145 Uiso 1 1 calc R . . N1 N 0.6750(3) 0.28533(13) 0.14468(18) 0.0389(8) Uani 1 1 d . . . H1 H 0.6130 0.2569 0.1160 0.047 Uiso 1 1 calc R . . N2 N 0.0626(3) 0.33377(14) 0.4019(2) 0.0432(8) Uani 1 1 d . . . H2 H 0.0033 0.3323 0.3517 0.052 Uiso 1 1 calc R . . N3 N 0.2583(4) 0.22578(15) 0.3946(2) 0.0514(9) Uani 1 1 d . . . H3 H 0.1674 0.2107 0.3984 0.062 Uiso 1 1 calc R . . O1 O 0.4944(3) 0.31408(12) -0.00080(17) 0.0535(8) Uani 1 1 d . . . O2 O 0.4801(3) 0.41766(12) 0.03161(16) 0.0508(7) Uani 1 1 d . . . O3 O 0.8290(3) 0.44042(14) 0.1427(2) 0.0693(9) Uani 1 1 d . . . O4 O 0.8650(3) 0.35347(13) 0.06736(18) 0.0540(8) Uani 1 1 d . B . O5 O 0.8867(3) 0.30577(14) 0.24194(17) 0.0589(8) Uani 1 1 d . . . O6 O 0.4164(3) 0.39759(15) 0.5089(2) 0.0661(9) Uani 1 1 d . . . O7 O 0.1940(3) 0.44761(12) 0.45734(17) 0.0545(8) Uani 1 1 d . . . O8 O 0.0723(3) 0.33206(12) 0.54165(16) 0.0475(7) Uani 1 1 d . . . O9 O 0.4626(4) 0.21411(15) 0.3306(2) 0.0704(9) Uani 1 1 d . . . O10 O 0.2646(4) 0.14248(13) 0.31152(19) 0.0631(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0384(19) 0.039(2) 0.037(2) -0.0046(15) 0.0088(15) -0.0032(15) C2 0.042(2) 0.036(2) 0.043(2) 0.0025(17) 0.0132(17) 0.0040(16) C3 0.042(2) 0.047(2) 0.047(2) 0.0029(18) 0.0106(18) -0.0050(17) C4 0.047(2) 0.044(2) 0.037(2) -0.0052(16) 0.0133(17) -0.0033(16) C5 0.044(2) 0.053(2) 0.036(2) -0.0047(17) 0.0121(16) -0.0047(17) C6 0.047(2) 0.047(2) 0.041(2) -0.0020(17) 0.0136(17) -0.0027(17) C7 0.048(2) 0.051(2) 0.031(2) 0.0015(16) 0.0120(16) -0.0051(17) C8 0.038(2) 0.047(2) 0.036(2) -0.0040(16) 0.0124(16) -0.0072(16) C9 0.047(2) 0.054(3) 0.040(2) -0.0020(17) 0.0146(19) -0.0097(19) C10 0.053(2) 0.047(2) 0.043(2) -0.0014(17) 0.0130(18) -0.0028(18) C11 0.065(3) 0.053(3) 0.054(3) 0.009(2) 0.002(2) 0.012(2) C12 0.083(3) 0.056(3) 0.052(3) 0.004(2) 0.017(2) 0.008(2) C13 0.052(3) 0.116(4) 0.087(4) -0.009(3) 0.034(3) -0.026(3) C14 0.046(4) 0.096(6) 0.093(6) -0.033(4) 0.018(3) -0.009(3) C14B 0.104(14) 0.085(13) 0.104(16) -0.018(11) 0.074(12) -0.008(10) C15 0.046(2) 0.057(2) 0.041(2) 0.0020(19) 0.0058(18) -0.0004(19) C16 0.070(3) 0.058(3) 0.064(3) 0.014(2) -0.008(2) 0.008(2) C17 0.090(3) 0.042(2) 0.063(3) -0.015(2) 0.021(2) -0.010(2) C18 0.101(4) 0.070(3) 0.062(4) -0.020(2) 0.022(3) -0.009(3) C19 0.047(2) 0.040(2) 0.036(2) -0.0040(16) 0.0099(19) -0.0025(16) C20 0.044(2) 0.054(2) 0.041(2) 0.0012(18) 0.0106(17) -0.0022(17) C21 0.061(3) 0.043(2) 0.049(3) 0.0001(18) 0.016(2) -0.001(2) C22 0.092(4) 0.052(3) 0.069(3) -0.011(2) 0.044(3) -0.001(2) C23 0.160(6) 0.064(3) 0.115(5) -0.045(3) 0.087(5) -0.036(3) C24 0.124(5) 0.081(4) 0.159(7) -0.004(4) 0.051(5) 0.041(4) C25 0.149(6) 0.091(4) 0.060(4) -0.011(3) 0.044(4) -0.019(4) N1 0.0387(16) 0.0366(17) 0.0401(19) 0.0041(13) 0.0042(13) -0.0017(12) N2 0.0391(17) 0.0521(19) 0.038(2) -0.0006(14) 0.0057(14) -0.0061(14) N3 0.057(2) 0.0459(18) 0.056(2) -0.0078(16) 0.0225(17) -0.0020(15) O1 0.0617(17) 0.0424(15) 0.0505(18) -0.0021(13) -0.0039(13) 0.0008(12) O2 0.0643(17) 0.0437(16) 0.0434(17) 0.0036(12) 0.0085(13) 0.0088(13) O3 0.0662(19) 0.0524(19) 0.096(3) -0.0137(16) 0.0316(17) -0.0189(15) O4 0.0443(15) 0.0677(18) 0.0550(18) -0.0111(14) 0.0220(13) -0.0115(13) O5 0.0546(17) 0.0719(19) 0.0452(17) -0.0046(14) -0.0023(13) -0.0068(14) O6 0.0478(17) 0.080(2) 0.066(2) -0.0236(16) 0.0011(15) -0.0083(14) O7 0.0699(18) 0.0435(16) 0.0492(18) -0.0057(12) 0.0093(14) -0.0024(14) O8 0.0519(15) 0.0499(16) 0.0419(17) -0.0027(12) 0.0123(13) -0.0035(12) O9 0.066(2) 0.072(2) 0.081(2) -0.0150(17) 0.0342(17) -0.0086(16) O10 0.083(2) 0.0473(17) 0.069(2) -0.0138(14) 0.0396(17) -0.0085(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.457(5) . ? C1 C2 1.526(5) . ? C1 C4 1.534(5) . ? C1 C3 1.550(5) . ? C2 O1 1.204(4) . ? C2 O2 1.334(4) . ? C3 O3 1.202(5) . ? C3 O4 1.335(5) . ? C4 C5 1.523(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.526(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.520(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.549(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N2 1.458(5) . ? C8 C9 1.531(5) . ? C8 C10 1.540(5) . ? C9 O6 1.205(4) . ? C9 O7 1.335(5) . ? C10 N3 1.443(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O2 1.471(5) . ? C11 C12 1.490(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 O4 1.456(5) . ? C13 C14 1.560(9) . ? C13 C14B 1.667(15) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C14B H14D 0.9800 . ? C14B H14E 0.9800 . ? C14B H14F 0.9800 . ? C15 O5 1.245(5) . ? C15 N1 1.347(5) . ? C15 C16 1.486(6) . ? C16 H16C 0.9800 . ? C16 H16B 0.9800 . ? C16 H16A 0.9800 . ? C17 O7 1.459(5) . ? C17 C18 1.491(7) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 O8 1.240(4) . ? C19 N2 1.345(5) . ? C19 C20 1.501(5) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 O9 1.214(5) . ? C21 O10 1.343(5) . ? C21 N3 1.366(5) . ? C22 O10 1.480(5) . ? C22 C25 1.499(7) . ? C22 C24 1.512(8) . ? C22 C23 1.523(7) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? N3 H3 0.8800 . ? 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 N1 C1 C2 106.4(3) . . ? N1 C1 C4 112.3(3) . . ? C2 C1 C4 113.4(3) . . ? N1 C1 C3 110.5(3) . . ? C2 C1 C3 105.5(3) . . ? C4 C1 C3 108.6(3) . . ? O1 C2 O2 124.2(3) . . ? O1 C2 C1 124.3(3) . . ? O2 C2 C1 111.5(3) . . ? O3 C3 O4 125.1(4) . . ? O3 C3 C1 124.2(4) . . ? O4 C3 C1 110.6(3) . . ? C5 C4 C1 114.6(3) . . ? C5 C4 H4A 108.6 . . ? C1 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? C1 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? C4 C5 C6 112.2(3) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 111.7(3) . . ? C7 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? C7 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C6 C7 C8 116.4(3) . . ? C6 C7 H7A 108.2 . . ? C8 C7 H7A 108.2 . . ? C6 C7 H7B 108.2 . . ? C8 C7 H7B 108.2 . . ? H7A C7 H7B 107.3 . . ? N2 C8 C9 112.0(3) . . ? N2 C8 C10 110.1(3) . . ? C9 C8 C10 107.8(3) . . ? N2 C8 C7 105.9(3) . . ? C9 C8 C7 109.4(3) . . ? C10 C8 C7 111.6(3) . . ? O6 C9 O7 124.5(4) . . ? O6 C9 C8 122.8(4) . . ? O7 C9 C8 112.6(3) . . ? N3 C10 C8 112.2(3) . . ? N3 C10 H10A 109.2 . . ? C8 C10 H10A 109.2 . . ? N3 C10 H10B 109.2 . . ? C8 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? O2 C11 C12 111.6(4) . . ? O2 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? O2 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O4 C13 C14 104.2(5) . . ? O4 C13 C14B 103.2(7) . . ? C14 C13 C14B 137.9(7) . . ? O4 C13 H13A 110.9 . . ? C14 C13 H13A 110.9 . . ? C14B C13 H13A 88.0 . . ? O4 C13 H13B 110.9 . . ? C14 C13 H13B 110.9 . . ? C14B C13 H13B 28.1 . . ? H13A C13 H13B 108.9 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? C13 C14B H14D 109.5 . . ? C13 C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? C13 C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 109.5 . . ? O5 C15 N1 120.1(4) . . ? O5 C15 C16 122.6(4) . . ? N1 C15 C16 117.3(4) . . ? C15 C16 H16C 109.5 . . ? C15 C16 H16B 109.5 . . ? H16C C16 H16B 109.5 . . ? C15 C16 H16A 109.5 . . ? H16C C16 H16A 109.5 . . ? H16B C16 H16A 109.5 . . ? O7 C17 C18 110.8(4) . . ? O7 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? O7 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O8 C19 N2 121.3(3) . . ? O8 C19 C20 122.6(4) . . ? N2 C19 C20 116.1(3) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O9 C21 O10 126.8(4) . . ? O9 C21 N3 123.6(4) . . ? O10 C21 N3 109.7(4) . . ? O10 C22 C25 109.4(4) . . ? O10 C22 C24 110.5(5) . . ? C25 C22 C24 111.7(5) . . ? O10 C22 C23 102.7(4) . . ? C25 C22 C23 110.1(5) . . ? C24 C22 C23 112.1(5) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C15 N1 C1 120.5(3) . . ? C15 N1 H1 119.8 . . ? C1 N1 H1 119.8 . . ? C19 N2 C8 123.9(3) . . ? C19 N2 H2 118.1 . . ? C8 N2 H2 118.1 . . ? C21 N3 C10 122.7(3) . . ? C21 N3 H3 118.6 . . ? C10 N3 H3 118.6 . . ? C2 O2 C11 116.3(3) . . ? C3 O4 C13 116.5(3) . . ? C9 O7 C17 116.4(3) . . ? C21 O10 C22 120.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 O1 -9.2(5) . . . . ? C4 C1 C2 O1 -133.0(4) . . . . ? C3 C1 C2 O1 108.3(4) . . . . ? N1 C1 C2 O2 172.2(3) . . . . ? C4 C1 C2 O2 48.4(4) . . . . ? C3 C1 C2 O2 -70.3(4) . . . . ? N1 C1 C3 O3 -141.4(4) . . . . ? C2 C1 C3 O3 104.0(4) . . . . ? C4 C1 C3 O3 -17.9(5) . . . . ? N1 C1 C3 O4 42.0(4) . . . . ? C2 C1 C3 O4 -72.6(4) . . . . ? C4 C1 C3 O4 165.5(3) . . . . ? N1 C1 C4 C5 -64.7(4) . . . . ? C2 C1 C4 C5 55.9(4) . . . . ? C3 C1 C4 C5 172.8(3) . . . . ? C1 C4 C5 C6 158.1(3) . . . . ? C4 C5 C6 C7 173.4(3) . . . . ? C5 C6 C7 C8 156.9(3) . . . . ? C6 C7 C8 N2 174.6(3) . . . . ? C6 C7 C8 C9 53.7(4) . . . . ? C6 C7 C8 C10 -65.5(4) . . . . ? N2 C8 C9 O6 144.6(4) . . . . ? C10 C8 C9 O6 23.3(5) . . . . ? C7 C8 C9 O6 -98.3(4) . . . . ? N2 C8 C9 O7 -38.6(4) . . . . ? C10 C8 C9 O7 -159.9(3) . . . . ? C7 C8 C9 O7 78.5(4) . . . . ? N2 C8 C10 N3 54.8(4) . . . . ? C9 C8 C10 N3 177.3(3) . . . . ? C7 C8 C10 N3 -62.5(4) . . . . ? O5 C15 N1 C1 -0.9(5) . . . . ? C16 C15 N1 C1 179.5(4) . . . . ? C2 C1 N1 C15 163.7(3) . . . . ? C4 C1 N1 C15 -71.8(4) . . . . ? C3 C1 N1 C15 49.6(4) . . . . ? O8 C19 N2 C8 2.8(5) . . . . ? C20 C19 N2 C8 -177.3(3) . . . . ? C9 C8 N2 C19 -52.5(5) . . . . ? C10 C8 N2 C19 67.5(4) . . . . ? C7 C8 N2 C19 -171.7(3) . . . . ? O9 C21 N3 C10 -4.1(6) . . . . ? O10 C21 N3 C10 175.9(3) . . . . ? C8 C10 N3 C21 108.7(4) . . . . ? O1 C2 O2 C11 -1.0(5) . . . . ? C1 C2 O2 C11 177.6(3) . . . . ? C12 C11 O2 C2 -80.6(4) . . . . ? O3 C3 O4 C13 9.0(6) . . . . ? C1 C3 O4 C13 -174.4(4) . . . . ? C14 C13 O4 C3 144.3(4) . . . . ? C14B C13 O4 C3 -68.0(8) . . . . ? O6 C9 O7 C17 -4.6(6) . . . . ? C8 C9 O7 C17 178.6(3) . . . . ? C18 C17 O7 C9 -80.0(5) . . . . ? O9 C21 O10 C22 -6.9(6) . . . . ? N3 C21 O10 C22 173.1(4) . . . . ? C25 C22 O10 C21 -60.4(6) . . . . ? C24 C22 O10 C21 63.1(6) . . . . ? C23 C22 O10 C21 -177.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 58.99 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.305 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.062 data_yl110708 _database_code_depnum_ccdc_archive 'CCDC 761462' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 N2 O7 Re' _chemical_formula_weight 459.42 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' Re Re -1.0185 7.2310 '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 6.7581(1) _cell_length_b 8.7934(2) _cell_length_c 11.4890(2) _cell_angle_alpha 86.1958(16) _cell_angle_beta 79.7708(16) _cell_angle_gamma 83.8740(17) _cell_volume 667.28(2) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 15985 _cell_measurement_theta_min 2.8718 _cell_measurement_theta_max 32.5592 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 9.139 _exptl_absorpt_correction_T_min 0.25846 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur Ruby' _diffrn_measurement_method '\o oscillation scan' _diffrn_detector_area_resol_mean 10.4498 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16418 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.99 _reflns_number_total 3211 _reflns_number_gt 3019 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis RED (Oxford, 2007)' _computing_cell_refinement 'CrysAlis RED (Oxford, 2007)' _computing_data_reduction 'CrysAlis RED (Oxford, 2007)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0337P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3211 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0192 _refine_ls_R_factor_gt 0.0177 _refine_ls_wR_factor_ref 0.0474 _refine_ls_wR_factor_gt 0.0469 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Re1 Re 0.669848(13) 0.449995(11) 0.240970(8) 0.02002(5) Uani 1 1 d . . . N1 N 0.7681(3) 0.6648(3) 0.2928(2) 0.0214(5) Uani 1 1 d . . . H1A H 0.6613 0.7313 0.3189 0.026 Uiso 1 1 calc R . . H1B H 0.8451 0.6460 0.3495 0.026 Uiso 1 1 calc R . . N2 N 0.6347(3) 0.6114(3) 0.0890(2) 0.0200(5) Uani 1 1 d . . . H2A H 0.6867 0.5649 0.0213 0.024 Uiso 1 1 calc R . . H2B H 0.5023 0.6378 0.0888 0.024 Uiso 1 1 calc R . . C1 C 0.6180(5) 0.2735(4) 0.1662(3) 0.0280(6) Uani 1 1 d . . . C2 C 0.3952(5) 0.4678(4) 0.3186(3) 0.0273(6) Uani 1 1 d . . . C3 C 0.7298(5) 0.3217(4) 0.3739(3) 0.0315(7) Uani 1 1 d . . . C4 C 1.0416(4) 0.5910(3) 0.1351(2) 0.0208(5) Uani 1 1 d . . . C5 C 0.7372(4) 0.7521(3) 0.0930(2) 0.0222(5) Uani 1 1 d . . . H5A H 0.6374 0.8365 0.1180 0.027 Uiso 1 1 calc R . . H5B H 0.8084 0.7791 0.0147 0.027 Uiso 1 1 calc R . . C6 C 0.8874(4) 0.7244(3) 0.1801(2) 0.0191(5) Uani 1 1 d . . . C7 C 0.9799(4) 0.8722(3) 0.1913(3) 0.0240(6) Uani 1 1 d . . . H7A H 0.8710 0.9517 0.2129 0.029 Uiso 1 1 calc R . . H7B H 1.0531 0.9023 0.1142 0.029 Uiso 1 1 calc R . . C8 C 1.1230(4) 0.8655(4) 0.2810(3) 0.0261(6) Uani 1 1 d . . . H8A H 1.0543 0.8308 0.3580 0.031 Uiso 1 1 calc R . . H8B H 1.2390 0.7925 0.2570 0.031 Uiso 1 1 calc R . . C9 C 1.1941(5) 1.0224(4) 0.2897(3) 0.0339(7) Uani 1 1 d . . . H9A H 1.2621 1.0572 0.2125 0.041 Uiso 1 1 calc R . . H9B H 1.0780 1.0951 0.3138 0.041 Uiso 1 1 calc R . . C10 C 1.3356(4) 1.0175(4) 0.3772(3) 0.0269(6) Uani 1 1 d . . . O1 O 0.5864(4) 0.1693(3) 0.1199(2) 0.0391(6) Uani 1 1 d . . . O2 O 0.2292(3) 0.4780(3) 0.3679(2) 0.0416(6) Uani 1 1 d . . . O3 O 0.7643(5) 0.2459(3) 0.4541(2) 0.0536(7) Uani 1 1 d . . . O4 O 0.9775(3) 0.4573(2) 0.15196(19) 0.0233(4) Uani 1 1 d . . . O5 O 1.2113(3) 0.6163(3) 0.08239(17) 0.0280(5) Uani 1 1 d . . . O6 O 1.4979(3) 0.9426(3) 0.36486(19) 0.0314(5) Uani 1 1 d . . . O7 O 1.2666(4) 1.1009(3) 0.4693(2) 0.0380(5) Uani 1 1 d . . . H7 H 1.3478 1.0904 0.5151 0.057 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 Re1 0.01734(7) 0.02246(7) 0.02090(7) -0.00130(4) -0.00448(4) -0.00260(4) N1 0.0184(10) 0.0266(13) 0.0196(11) -0.0057(9) -0.0026(8) -0.0028(9) N2 0.0125(10) 0.0270(13) 0.0218(11) -0.0041(9) -0.0055(8) -0.0014(9) C1 0.0259(14) 0.0300(16) 0.0284(15) -0.0006(12) -0.0048(11) -0.0048(12) C2 0.0278(14) 0.0281(16) 0.0255(14) 0.0010(12) -0.0033(11) -0.0043(12) C3 0.0367(17) 0.0319(17) 0.0287(15) 0.0010(13) -0.0109(13) -0.0093(14) C4 0.0145(11) 0.0309(15) 0.0192(12) -0.0065(11) -0.0077(9) -0.0013(10) C5 0.0179(12) 0.0245(14) 0.0256(13) 0.0008(11) -0.0078(10) -0.0035(10) C6 0.0151(11) 0.0219(13) 0.0210(12) -0.0015(10) -0.0047(9) -0.0028(10) C7 0.0191(12) 0.0248(14) 0.0297(14) -0.0015(11) -0.0067(10) -0.0049(11) C8 0.0245(13) 0.0293(15) 0.0275(14) -0.0035(12) -0.0097(11) -0.0069(12) C9 0.0324(16) 0.0271(16) 0.0480(19) -0.0032(14) -0.0209(14) -0.0050(13) C10 0.0246(14) 0.0247(15) 0.0338(15) -0.0053(12) -0.0074(11) -0.0063(12) O1 0.0533(15) 0.0270(12) 0.0413(13) -0.0032(10) -0.0135(11) -0.0130(11) O2 0.0255(11) 0.0488(16) 0.0465(14) -0.0021(12) 0.0067(10) -0.0070(11) O3 0.073(2) 0.0475(17) 0.0442(15) 0.0167(13) -0.0256(14) -0.0099(15) O4 0.0151(9) 0.0259(11) 0.0291(10) -0.0074(8) -0.0045(7) 0.0023(8) O5 0.0136(9) 0.0440(13) 0.0273(10) -0.0109(9) -0.0021(7) -0.0033(9) O6 0.0246(10) 0.0374(13) 0.0339(11) -0.0126(10) -0.0082(8) 0.0015(9) O7 0.0329(12) 0.0406(14) 0.0433(13) -0.0184(11) -0.0163(10) 0.0104(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C2 1.906(3) . ? Re1 C3 1.914(3) . ? Re1 C1 1.915(3) . ? Re1 O4 2.154(2) . ? Re1 N2 2.206(2) . ? Re1 N1 2.218(2) . ? N1 C6 1.493(3) . ? N2 C5 1.488(4) . ? C1 O1 1.147(4) . ? C2 O2 1.161(4) . ? C3 O3 1.144(4) . ? C4 O5 1.233(3) . ? C4 O4 1.287(4) . ? C4 C6 1.535(4) . ? C5 C6 1.539(4) . ? C6 C7 1.523(4) . ? C7 C8 1.528(4) . ? C8 C9 1.524(4) . ? C9 C10 1.501(4) . ? C10 O6 1.208(4) . ? C10 O7 1.315(4) . ? 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 Re1 C3 87.28(14) . . ? C2 Re1 C1 88.91(13) . . ? C3 Re1 C1 89.67(14) . . ? C2 Re1 O4 173.61(10) . . ? C3 Re1 O4 96.49(12) . . ? C1 Re1 O4 96.25(11) . . ? C2 Re1 N2 97.86(11) . . ? C3 Re1 N2 172.90(11) . . ? C1 Re1 N2 95.29(11) . . ? O4 Re1 N2 77.96(8) . . ? C2 Re1 N1 100.11(12) . . ? C3 Re1 N1 97.85(12) . . ? C1 Re1 N1 168.48(10) . . ? O4 Re1 N1 74.32(8) . . ? N2 Re1 N1 76.49(9) . . ? C6 N1 Re1 103.01(16) . . ? C5 N2 Re1 111.97(16) . . ? O1 C1 Re1 178.9(3) . . ? O2 C2 Re1 178.7(3) . . ? O3 C3 Re1 179.4(4) . . ? O5 C4 O4 124.3(3) . . ? O5 C4 C6 120.1(3) . . ? O4 C4 C6 115.5(2) . . ? N2 C5 C6 109.9(2) . . ? N1 C6 C7 114.2(2) . . ? N1 C6 C4 105.7(2) . . ? C7 C6 C4 114.3(2) . . ? N1 C6 C5 105.2(2) . . ? C7 C6 C5 109.7(2) . . ? C4 C6 C5 107.1(2) . . ? C6 C7 C8 115.9(2) . . ? C9 C8 C7 110.8(2) . . ? C10 C9 C8 111.4(3) . . ? O6 C10 O7 122.8(3) . . ? O6 C10 C9 123.1(3) . . ? O7 C10 C9 114.1(3) . . ? C4 O4 Re1 115.83(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.899 _refine_diff_density_min -0.623 _refine_diff_density_rms 0.120