# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Hong, Bor-Cherng' _publ_contact_author_email chebch@ccu.edu.tw _publ_section_title ; Enantioselective Organocatalytic Domino Michael-Acetalization-Henry Reactions of 2-Hydroxynitrostyrene and Aldehyde for the Synthesis of Tetrahydro-6H-benzo[c]chromenones ; loop_ _publ_author_name B.-C.Hong P.Kotame J.-H.Liao # Attachment '3a.cif' data_pmk0223 _database_code_depnum_ccdc_archive 'CCDC 794373' #TrackingRef '3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N O4' _chemical_absolute_configuration syn _chemical_formula_weight 235.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.6540(9) _cell_length_b 7.4586(12) _cell_length_c 13.100(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.649(3) _cell_angle_gamma 90.00 _cell_volume 544.62(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 586 _cell_measurement_theta_min -23.529 _cell_measurement_theta_max 23.529 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9929 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Smart Apex' _diffrn_measurement_method 'phi-omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5325 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.25 _reflns_number_total 1960 _reflns_number_gt 1759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep-3 _computing_publication_material 'Wingx publication routines (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^)+(0.0446P)^2^+0.0563P] 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 -0.6(13) _refine_ls_number_reflns 1960 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 O1 O 0.4710(3) 0.7116(2) 0.13997(11) 0.0195(4) Uani 1 1 d . . . O2 O 0.6099(3) 0.9757(2) 0.19217(12) 0.0234(4) Uani 1 1 d . . . O3 O 0.6371(3) 0.6838(3) 0.37246(14) 0.0361(5) Uani 1 1 d . . . O4 O 0.5219(3) 0.4232(2) 0.41492(14) 0.0381(5) Uani 1 1 d . . . N1 N 0.4827(4) 0.5806(3) 0.39161(14) 0.0216(4) Uani 1 1 d . . . C1 C 0.1235(4) 0.5779(3) 0.19827(15) 0.0154(5) Uani 1 1 d . . . C2 C -0.0463(4) 0.4409(3) 0.18495(17) 0.0179(5) Uani 1 1 d . . . H2 H -0.1671 0.4380 0.2273 0.021 Uiso 1 1 calc R . . C3 C -0.0420(4) 0.3085(3) 0.11078(17) 0.0204(5) Uani 1 1 d . . . H3 H -0.1595 0.2163 0.1024 0.025 Uiso 1 1 calc R . . C4 C 0.1345(4) 0.3113(3) 0.04891(17) 0.0206(5) Uani 1 1 d . . . H4 H 0.1393 0.2199 -0.0012 0.025 Uiso 1 1 calc R . . C5 C 0.3040(4) 0.4473(3) 0.06025(17) 0.0195(5) Uani 1 1 d . . . H5 H 0.4249 0.4504 0.0179 0.023 Uiso 1 1 calc R . . C6 C 0.2945(4) 0.5783(3) 0.13387(17) 0.0173(5) Uani 1 1 d . . . C7 C 0.4522(4) 0.8683(3) 0.19313(17) 0.0182(5) Uani 1 1 d . . . C8 C 0.2326(4) 0.8969(3) 0.24235(17) 0.0159(5) Uani 1 1 d . . . H8 H 0.1070 0.9444 0.1859 0.019 Uiso 1 1 calc R . . C9 C 0.1272(4) 0.7220(3) 0.27916(16) 0.0164(5) Uani 1 1 d . . . H9 H -0.0448 0.7488 0.2822 0.020 Uiso 1 1 calc R . . C10 C 0.2354(4) 0.6520(3) 0.38676(17) 0.0175(5) Uani 1 1 d . . . H10A H 0.2386 0.7505 0.4376 0.021 Uiso 1 1 calc R . . H10B H 0.1312 0.5558 0.4066 0.021 Uiso 1 1 calc R . . C11 C 0.2777(4) 1.0468(3) 0.32295(17) 0.0191(5) Uani 1 1 d . . . H11A H 0.4125 1.0110 0.3775 0.023 Uiso 1 1 calc R . . H11B H 0.3272 1.1561 0.2892 0.023 Uiso 1 1 calc R . . C12 C 0.0616(4) 1.0920(3) 0.37381(18) 0.0227(5) Uani 1 1 d . . . H12A H 0.0204 0.9881 0.4131 0.034 Uiso 1 1 calc R . . H12B H -0.0752 1.1229 0.3203 0.034 Uiso 1 1 calc R . . H12C H 0.1005 1.1941 0.4207 0.034 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 O1 0.0190(8) 0.0180(8) 0.0232(8) -0.0030(7) 0.0085(6) -0.0024(7) O2 0.0245(9) 0.0217(9) 0.0248(9) 0.0014(7) 0.0065(7) -0.0083(8) O3 0.0236(9) 0.0456(12) 0.0418(11) 0.0209(10) 0.0138(8) 0.0075(9) O4 0.0430(11) 0.0170(10) 0.0468(12) -0.0010(9) -0.0139(9) 0.0086(8) N1 0.0278(11) 0.0222(12) 0.0146(10) 0.0000(9) 0.0032(8) 0.0034(9) C1 0.0158(11) 0.0126(11) 0.0170(11) 0.0022(10) 0.0005(9) 0.0039(10) C2 0.0171(12) 0.0148(12) 0.0216(12) 0.0032(10) 0.0028(10) 0.0003(9) C3 0.0199(12) 0.0139(12) 0.0255(13) 0.0000(10) -0.0017(10) -0.0030(10) C4 0.0258(13) 0.0146(12) 0.0199(12) -0.0036(10) -0.0004(10) 0.0050(10) C5 0.0218(12) 0.0207(13) 0.0157(11) 0.0005(10) 0.0028(9) 0.0060(10) C6 0.0158(11) 0.0155(11) 0.0200(12) 0.0047(10) 0.0006(9) 0.0006(9) C7 0.0237(13) 0.0171(13) 0.0134(11) 0.0043(9) 0.0018(10) -0.0006(10) C8 0.0185(11) 0.0114(11) 0.0174(11) 0.0020(9) 0.0024(9) -0.0013(9) C9 0.0168(11) 0.0143(11) 0.0189(11) -0.0007(10) 0.0053(9) 0.0004(9) C10 0.0202(11) 0.0138(11) 0.0198(11) 0.0002(9) 0.0074(10) -0.0023(9) C11 0.0223(12) 0.0151(13) 0.0197(12) 0.0004(10) 0.0025(9) -0.0029(9) C12 0.0285(13) 0.0154(13) 0.0243(12) -0.0029(10) 0.0050(10) -0.0004(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 O1 C7 1.374(3) . ? O1 C6 1.401(3) . ? O2 C7 1.200(3) . ? O3 N1 1.221(3) . ? O4 N1 1.224(3) . ? N1 C10 1.488(3) . ? C1 C6 1.386(3) . ? C1 C2 1.393(3) . ? C1 C9 1.507(3) . ? C2 C3 1.388(3) . ? C2 H2 0.9500 . ? C3 C4 1.387(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C4 H4 0.9500 . ? C5 C6 1.380(3) . ? C5 H5 0.9500 . ? C7 C8 1.507(3) . ? C8 C11 1.529(3) . ? C8 C9 1.545(3) . ? C8 H8 1.0000 . ? C9 C10 1.531(3) . ? C9 H9 1.0000 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.524(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 C7 O1 C6 121.18(17) . . ? O3 N1 O4 123.4(2) . . ? O3 N1 C10 117.69(19) . . ? O4 N1 C10 118.9(2) . . ? C6 C1 C2 117.5(2) . . ? C6 C1 C9 119.83(19) . . ? C2 C1 C9 122.63(19) . . ? C3 C2 C1 121.1(2) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.0(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 119.1(2) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C1 122.4(2) . . ? C5 C6 O1 115.57(19) . . ? C1 C6 O1 122.0(2) . . ? O2 C7 O1 116.21(19) . . ? O2 C7 C8 125.2(2) . . ? O1 C7 C8 118.45(18) . . ? C7 C8 C11 110.16(18) . . ? C7 C8 C9 113.76(17) . . ? C11 C8 C9 115.48(17) . . ? C7 C8 H8 105.5 . . ? C11 C8 H8 105.5 . . ? C9 C8 H8 105.5 . . ? C1 C9 C10 111.12(18) . . ? C1 C9 C8 110.09(17) . . ? C10 C9 C8 117.38(18) . . ? C1 C9 H9 105.8 . . ? C10 C9 H9 105.8 . . ? C8 C9 H9 105.8 . . ? N1 C10 C9 112.89(17) . . ? N1 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? N1 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C8 114.23(19) . . ? C12 C11 H11A 108.7 . . ? C8 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C8 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.200 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.041 # Attachment '3b.cif' data_pmk02364 _database_code_depnum_ccdc_archive 'CCDC 794374' #TrackingRef '3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 Br N O4' _chemical_formula_sum 'C12 H12 Br N O4' _chemical_absolute_configuration ad _chemical_formula_weight 314.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 6.8992(8) _cell_length_b 6.9979(8) _cell_length_c 24.978(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1205.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 526 _cell_measurement_theta_min -23.529 _cell_measurement_theta_max 23.529 _exptl_crystal_description chunky _exptl_crystal_colour colorless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.730 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 3.415 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9929 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Smart Apex' _diffrn_measurement_method 'phi-omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13963 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 28.32 _reflns_number_total 2924 _reflns_number_gt 2621 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep-3 _computing_publication_material 'Wingx publication routines (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^)+(0.0235P)^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 0.006(8) _refine_ls_number_reflns 2924 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0500 _refine_ls_wR_factor_gt 0.0492 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.35629(3) -0.14477(3) -0.067187(9) 0.02299(7) Uani 1 1 d . . . O1 O 0.3560(2) 0.46166(19) 0.10429(6) 0.0191(3) Uani 1 1 d . . . O2 O 0.3522(3) 0.5579(2) 0.18763(6) 0.0255(4) Uani 1 1 d . . . O3 O 0.8318(2) -0.0124(2) 0.14393(6) 0.0230(4) Uani 1 1 d . . . O4 O 0.6719(3) 0.2496(2) 0.15467(7) 0.0241(4) Uani 1 1 d . . . N1 N 0.6806(3) 0.0756(3) 0.15139(7) 0.0157(4) Uani 1 1 d . . . C1 C 0.3338(3) -0.0133(3) 0.04027(8) 0.0158(5) Uani 1 1 d . . . H1 H 0.3214 -0.1423 0.0485 0.019 Uiso 1 1 calc R . . C2 C 0.3535(4) 0.0430(3) -0.01213(8) 0.0183(5) Uani 1 1 d . . . C3 C 0.3667(4) 0.2342(3) -0.02588(9) 0.0196(5) Uani 1 1 d . . . H3A H 0.3764 0.2702 -0.0616 0.024 Uiso 1 1 calc R . . C4 C 0.3653(3) 0.3705(3) 0.01388(8) 0.0184(4) Uani 1 1 d . . . H4A H 0.3755 0.4994 0.0052 0.022 Uiso 1 1 calc R . . C5 C 0.3486(3) 0.3142(3) 0.06685(9) 0.0171(4) Uani 1 1 d . . . C6 C 0.3322(3) 0.1228(3) 0.08121(8) 0.0143(4) Uani 1 1 d . . . C7 C 0.3159(3) 0.0654(3) 0.13940(9) 0.0144(5) Uani 1 1 d . . . H7 H 0.2121 -0.0301 0.1409 0.017 Uiso 1 1 calc R . . C8 C 0.2446(3) 0.2351(3) 0.17348(9) 0.0163(5) Uani 1 1 d . . . H8 H 0.1050 0.2436 0.1665 0.020 Uiso 1 1 calc R . . C9 C 0.3255(3) 0.4272(3) 0.15762(9) 0.0196(5) Uani 1 1 d . . . C10 C 0.2624(3) 0.2060(3) 0.23367(9) 0.0192(5) Uani 1 1 d . . . H10A H 0.2243 0.3229 0.2517 0.023 Uiso 1 1 calc R . . H10B H 0.3972 0.1816 0.2424 0.023 Uiso 1 1 calc R . . C11 C 0.1395(4) 0.0419(3) 0.25505(9) 0.0258(5) Uani 1 1 d . . . H11A H 0.0058 0.0643 0.2464 0.039 Uiso 1 1 calc R . . H11B H 0.1542 0.0338 0.2932 0.039 Uiso 1 1 calc R . . H11C H 0.1811 -0.0758 0.2390 0.039 Uiso 1 1 calc R . . C12 C 0.4987(3) -0.0374(3) 0.15829(9) 0.0160(5) Uani 1 1 d . . . H12A H 0.4840 -0.0691 0.1959 0.019 Uiso 1 1 calc R . . H12B H 0.5112 -0.1563 0.1386 0.019 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02735(11) 0.02398(10) 0.01763(10) -0.00038(10) -0.00185(11) 0.00098(11) O1 0.0221(8) 0.0108(7) 0.0245(8) 0.0030(6) -0.0001(8) -0.0016(8) O2 0.0280(9) 0.0152(7) 0.0333(9) -0.0087(7) 0.0045(9) -0.0059(8) O3 0.0160(9) 0.0253(8) 0.0277(9) -0.0013(7) -0.0004(8) 0.0016(8) O4 0.0234(10) 0.0117(8) 0.0371(10) -0.0002(7) -0.0001(8) -0.0039(7) N1 0.0157(10) 0.0177(9) 0.0136(9) 0.0007(7) -0.0032(8) -0.0034(8) C1 0.0117(11) 0.0133(10) 0.0224(12) 0.0027(8) 0.0000(10) 0.0007(9) C2 0.0147(11) 0.0210(11) 0.0191(11) -0.0011(9) -0.0037(11) -0.0014(12) C3 0.0138(11) 0.0268(11) 0.0181(11) 0.0086(9) -0.0024(11) -0.0021(12) C4 0.0133(10) 0.0148(10) 0.0273(11) 0.0078(9) -0.0007(10) -0.0003(12) C5 0.0121(9) 0.0142(9) 0.0250(11) 0.0024(9) -0.0014(14) -0.0006(8) C6 0.0083(10) 0.0160(10) 0.0187(11) 0.0043(8) -0.0028(8) -0.0010(9) C7 0.0092(12) 0.0130(9) 0.0209(12) 0.0010(9) -0.0025(9) -0.0020(8) C8 0.0158(12) 0.0137(10) 0.0194(12) -0.0017(9) 0.0004(10) -0.0035(9) C9 0.0118(12) 0.0168(10) 0.0302(13) 0.0002(10) 0.0007(10) 0.0003(9) C10 0.0188(12) 0.0175(11) 0.0213(13) -0.0028(9) -0.0035(10) 0.0000(9) C11 0.0294(13) 0.0286(12) 0.0194(12) 0.0021(10) 0.0018(12) -0.0022(13) C12 0.0140(11) 0.0135(11) 0.0204(12) 0.0030(9) 0.0008(9) -0.0025(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C2 1.902(2) . ? O1 C9 1.370(3) . ? O1 C5 1.393(2) . ? O2 C9 1.196(3) . ? O3 N1 1.225(2) . ? O4 N1 1.222(2) . ? N1 C12 1.493(3) . ? C1 C2 1.373(3) . ? C1 C6 1.398(3) . ? C1 H1 0.9300 . ? C2 C3 1.384(3) . ? C3 C4 1.377(3) . ? C3 H3A 0.9300 . ? C4 C5 1.385(3) . ? C4 H4A 0.9300 . ? C5 C6 1.391(3) . ? C6 C7 1.512(3) . ? C7 C12 1.526(3) . ? C7 C8 1.542(3) . ? C7 H7 0.9800 . ? C8 C9 1.509(3) . ? C8 C10 1.522(3) . ? C8 H8 0.9800 . ? C10 C11 1.524(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? 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 C5 121.11(16) . . ? O4 N1 O3 123.57(19) . . ? O4 N1 C12 118.56(19) . . ? O3 N1 C12 117.84(17) . . ? C2 C1 C6 120.16(19) . . ? C2 C1 H1 119.9 . . ? C6 C1 H1 119.9 . . ? C1 C2 C3 121.3(2) . . ? C1 C2 Br1 119.46(16) . . ? C3 C2 Br1 119.18(16) . . ? C4 C3 C2 119.4(2) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C3 C4 C5 119.5(2) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C4 C5 C6 121.8(2) . . ? C4 C5 O1 115.30(17) . . ? C6 C5 O1 122.89(19) . . ? C5 C6 C1 117.84(19) . . ? C5 C6 C7 120.65(18) . . ? C1 C6 C7 121.51(18) . . ? C6 C7 C12 111.15(18) . . ? C6 C7 C8 110.46(17) . . ? C12 C7 C8 117.11(18) . . ? C6 C7 H7 105.7 . . ? C12 C7 H7 105.7 . . ? C8 C7 H7 105.7 . . ? C9 C8 C10 110.41(19) . . ? C9 C8 C7 115.04(18) . . ? C10 C8 C7 114.61(19) . . ? C9 C8 H8 105.2 . . ? C10 C8 H8 105.2 . . ? C7 C8 H8 105.2 . . ? O2 C9 O1 116.82(19) . . ? O2 C9 C8 125.0(2) . . ? O1 C9 C8 117.96(19) . . ? C8 C10 C11 113.70(19) . . ? C8 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C8 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 C7 114.18(18) . . ? N1 C12 H12A 108.7 . . ? C7 C12 H12A 108.7 . . ? N1 C12 H12B 108.7 . . ? C7 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.512 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.064 # Attachment '3m.cif' data_pmk02393 _database_code_depnum_ccdc_archive 'CCDC 794375' #TrackingRef '3m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 N O6' _chemical_absolute_configuration unk _chemical_formula_weight 281.26 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 monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall P2yb loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.331(2) _cell_length_b 7.848(3) _cell_length_c 14.735(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.877(6) _cell_angle_gamma 90.00 _cell_volume 613.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 839 _cell_measurement_theta_min -23.529 _cell_measurement_theta_max 23.529 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9848 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Smart Apex' _diffrn_measurement_method 'phi-omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7028 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 28.32 _reflns_number_total 2885 _reflns_number_gt 2823 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep-3 _computing_publication_material 'Wingx publication routines (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^)+(0.0499P)^2^+0.1669P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.6(8) _refine_ls_number_reflns 2885 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 O1 O 0.37202(18) 0.31234(15) 0.84498(7) 0.0168(2) Uani 1 1 d . . . O2 O 0.22375(19) 0.42468(14) 0.71494(7) 0.0185(2) Uani 1 1 d . . . O3 O 0.9758(2) -0.17421(16) 0.75768(8) 0.0246(3) Uani 1 1 d . . . O4 O 0.6049(3) -0.28141(17) 0.76667(11) 0.0372(3) Uani 1 1 d . . . O5 O 0.8526(2) -0.00288(16) 0.58008(7) 0.0188(2) Uani 1 1 d . . . H5 H 0.9084 -0.1030 0.5834 0.028 Uiso 1 1 calc R . . O6 O 0.0663(2) 0.68451(16) 0.57912(9) 0.0259(3) Uani 1 1 d . . . N1 N 0.7452(3) -0.16406(17) 0.75098(9) 0.0192(3) Uani 1 1 d . . . C1 C 0.9527(3) 0.0781(2) 0.92453(10) 0.0164(3) Uani 1 1 d . . . H1 H 1.0907 0.0219 0.9015 0.020 Uiso 1 1 calc R . . C2 C 0.9389(3) 0.0847(2) 1.01800(10) 0.0178(3) Uani 1 1 d . . . H2 H 1.0659 0.0319 1.0584 0.021 Uiso 1 1 calc R . . C3 C 0.7391(3) 0.1686(2) 1.05263(10) 0.0183(3) Uani 1 1 d . . . H3A H 0.7302 0.1729 1.1167 0.022 Uiso 1 1 calc R . . C4 C 0.5532(3) 0.2459(2) 0.99406(10) 0.0175(3) Uani 1 1 d . . . H4 H 0.4168 0.3037 1.0172 0.021 Uiso 1 1 calc R . . C5 C 0.5703(3) 0.23707(19) 0.90098(10) 0.0150(3) Uani 1 1 d . . . C6 C 0.7660(3) 0.15306(19) 0.86385(9) 0.0138(3) Uani 1 1 d . . . C7 C 0.7687(3) 0.15278(19) 0.76153(9) 0.0127(3) Uani 1 1 d . . . H7 H 0.9477 0.1466 0.7471 0.015 Uiso 1 1 calc R . . C8 C 0.6518(3) 0.32020(18) 0.72244(9) 0.0135(3) Uani 1 1 d . . . H8 H 0.7694 0.4145 0.7440 0.016 Uiso 1 1 calc R . . C9 C 0.4009(3) 0.35736(19) 0.75775(10) 0.0145(3) Uani 1 1 d . . . C10 C 0.6266(3) 0.32304(19) 0.61821(10) 0.0157(3) Uani 1 1 d . . . H10A H 0.7965 0.3246 0.5967 0.019 Uiso 1 1 calc R . . H10B H 0.5372 0.4280 0.5961 0.019 Uiso 1 1 calc R . . C11 C 0.4809(3) 0.1669(2) 0.57864(10) 0.0181(3) Uani 1 1 d . . . H11A H 0.3074 0.1694 0.5969 0.022 Uiso 1 1 calc R . . H11B H 0.4693 0.1712 0.5112 0.022 Uiso 1 1 calc R . . C12 C 0.6092(3) 0.0017(2) 0.61180(9) 0.0162(3) Uani 1 1 d . . . H12 H 0.5074 -0.0978 0.5866 0.019 Uiso 1 1 calc R . . C13 C 0.6239(3) 0.00018(19) 0.71694(9) 0.0143(3) Uani 1 1 d . . . H13 H 0.4481 0.0030 0.7349 0.017 Uiso 1 1 calc R . . H6A H 0.089(4) 0.625(3) 0.5335(18) 0.034(6) Uiso 1 1 d . . . H6B H 0.107(5) 0.629(4) 0.6218(19) 0.038(7) Uiso 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 O1 0.0133(5) 0.0211(6) 0.0161(5) 0.0005(4) 0.0018(4) 0.0028(4) O2 0.0150(5) 0.0183(5) 0.0219(5) 0.0017(4) 0.0000(4) 0.0023(4) O3 0.0284(6) 0.0239(6) 0.0211(5) 0.0000(5) -0.0002(4) 0.0092(5) O4 0.0454(8) 0.0161(6) 0.0527(9) 0.0083(6) 0.0174(7) -0.0031(6) O5 0.0210(5) 0.0176(5) 0.0187(5) 0.0013(4) 0.0068(4) 0.0030(4) O6 0.0399(7) 0.0220(6) 0.0158(5) 0.0007(5) 0.0031(5) 0.0116(5) N1 0.0296(7) 0.0144(6) 0.0145(5) -0.0008(5) 0.0058(5) 0.0032(5) C1 0.0147(7) 0.0146(7) 0.0199(7) 0.0006(6) 0.0007(5) 0.0001(5) C2 0.0185(7) 0.0149(6) 0.0192(7) 0.0037(6) -0.0029(5) -0.0025(6) C3 0.0219(7) 0.0182(7) 0.0143(6) -0.0009(6) -0.0002(5) -0.0048(6) C4 0.0184(7) 0.0164(7) 0.0179(7) -0.0024(6) 0.0030(5) -0.0021(6) C5 0.0133(6) 0.0138(7) 0.0176(7) 0.0003(5) -0.0003(5) -0.0020(5) C6 0.0139(6) 0.0123(6) 0.0152(6) -0.0001(5) 0.0006(5) -0.0027(5) C7 0.0125(6) 0.0117(6) 0.0139(6) 0.0005(5) 0.0014(5) 0.0013(5) C8 0.0120(6) 0.0128(7) 0.0157(6) 0.0010(5) 0.0020(5) -0.0004(5) C9 0.0141(6) 0.0124(6) 0.0169(6) -0.0015(5) 0.0005(5) -0.0022(5) C10 0.0176(6) 0.0142(7) 0.0155(6) 0.0034(5) 0.0027(5) 0.0017(5) C11 0.0198(7) 0.0203(7) 0.0137(6) 0.0002(6) 0.0002(5) 0.0014(6) C12 0.0190(7) 0.0152(7) 0.0145(6) -0.0010(6) 0.0023(5) -0.0011(6) C13 0.0163(6) 0.0121(6) 0.0148(6) 0.0003(5) 0.0024(5) 0.0001(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 O1 C9 1.3569(18) . ? O1 C5 1.4029(17) . ? O2 C9 1.2030(18) . ? O3 N1 1.226(2) . ? O4 N1 1.223(2) . ? O5 C12 1.4240(18) . ? O5 H5 0.8400 . ? O6 H6A 0.84(3) . ? O6 H6B 0.78(3) . ? N1 C13 1.505(2) . ? C1 C2 1.388(2) . ? C1 C6 1.398(2) . ? C1 H1 0.9500 . ? C2 C3 1.393(2) . ? C2 H2 0.9500 . ? C3 C4 1.386(2) . ? C3 H3A 0.9500 . ? C4 C5 1.386(2) . ? C4 H4 0.9500 . ? C5 C6 1.393(2) . ? C6 C7 1.5092(19) . ? C7 C13 1.5355(19) . ? C7 C8 1.540(2) . ? C7 H7 1.0000 . ? C8 C9 1.512(2) . ? C8 C10 1.528(2) . ? C8 H8 1.0000 . ? C10 C11 1.534(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.523(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.5433(19) . ? C12 H12 1.0000 . ? C13 H13 1.0000 . ? 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 C5 121.00(11) . . ? C12 O5 H5 109.5 . . ? H6A O6 H6B 106(3) . . ? O4 N1 O3 124.29(14) . . ? O4 N1 C13 117.25(14) . . ? O3 N1 C13 118.39(13) . . ? C2 C1 C6 120.85(14) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C1 C2 C3 120.09(14) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.26(14) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 118.65(13) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C4 C5 C6 122.70(13) . . ? C4 C5 O1 116.06(12) . . ? C6 C5 O1 121.19(13) . . ? C5 C6 C1 117.44(13) . . ? C5 C6 C7 118.50(12) . . ? C1 C6 C7 124.03(13) . . ? C6 C7 C13 111.89(11) . . ? C6 C7 C8 109.11(11) . . ? C13 C7 C8 109.81(11) . . ? C6 C7 H7 108.7 . . ? C13 C7 H7 108.7 . . ? C8 C7 H7 108.7 . . ? C9 C8 C10 110.66(11) . . ? C9 C8 C7 111.96(11) . . ? C10 C8 C7 112.26(11) . . ? C9 C8 H8 107.2 . . ? C10 C8 H8 107.2 . . ? C7 C8 H8 107.2 . . ? O2 C9 O1 116.86(13) . . ? O2 C9 C8 125.37(13) . . ? O1 C9 C8 117.77(12) . . ? C8 C10 C11 111.08(12) . . ? C8 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C8 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 111.42(12) . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? O5 C12 C11 108.09(12) . . ? O5 C12 C13 112.02(12) . . ? C11 C12 C13 107.68(12) . . ? O5 C12 H12 109.7 . . ? C11 C12 H12 109.7 . . ? C13 C12 H12 109.7 . . ? N1 C13 C7 110.21(11) . . ? N1 C13 C12 108.49(11) . . ? C7 C13 C12 113.28(11) . . ? N1 C13 H13 108.2 . . ? C7 C13 H13 108.2 . . ? C12 C13 H13 108.2 . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.393 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.052