# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email kotukamoto@huhs.ac.jp _publ_contact_author_name 'K. Tsukamoto' loop_ _publ_author_name K.Tsukamoto Y.Shinohara S.Iwasaki H.Maeda data_ac5 _database_code_depnum_ccdc_archive 'CCDC 803556' #TrackingRef 'web_deposit_cif_file_0_KojiTsukamoto_1297836831.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O4 S, H2 O' _chemical_formula_sum 'C12 H12 N2 O5 S' _chemical_formula_weight 296.31 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' S S 0.3331 0.5567 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 5.6878(1) _cell_length_b 9.3529(8) _cell_length_c 24.3327(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.498(1) _cell_angle_gamma 90.00 _cell_volume 1294.39(12) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9784 _cell_measurement_theta_min 7.27 _cell_measurement_theta_max 136.21 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 2.448 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.611 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details '(NUMABS; Higashi, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14331 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 68.16 _reflns_number_total 2369 _reflns_number_gt 1481 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 2003)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson et al., 1996)' _computing_publication_material SHELXL-97 _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^)+(0.0989P)^2^+1.4021P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2369 _refine_ls_number_parameters 194 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.2058 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 S1 S -0.26804(19) 0.34740(12) 0.04001(5) 0.0639(4) Uani 1 1 d . . . O1 O 0.5366(5) 0.3919(3) 0.17572(11) 0.0563(7) Uani 1 1 d . . . O2 O 0.4160(5) 0.6043(3) 0.15007(14) 0.0699(9) Uani 1 1 d . . . O3 O 0.8457(5) -0.0495(3) 0.23380(13) 0.0689(9) Uani 1 1 d . . . H3O H 0.8326 -0.1351 0.2270 0.103 Uiso 1 1 calc R . . O4 O -0.0022(6) 0.7904(4) 0.08530(16) 0.0883(11) Uani 1 1 d . . . N1 N 0.0387(6) 0.5119(4) 0.09549(15) 0.0570(9) Uani 1 1 d . . . H1N H 0.077(8) 0.596(5) 0.1018(19) 0.068 Uiso 1 1 d . . . N2 N -0.2449(6) 0.6267(4) 0.04476(15) 0.0588(9) Uani 1 1 d . . . H2N H -0.370(9) 0.617(5) 0.024(2) 0.071 Uiso 1 1 d . . . C1 C 0.3803(7) 0.4771(4) 0.14871(17) 0.0566(10) Uani 1 1 d . . . C2 C 0.1817(7) 0.4089(4) 0.12048(16) 0.0534(10) Uani 1 1 d . . . C3 C 0.1591(7) 0.2653(4) 0.12131(16) 0.0553(10) Uani 1 1 d . . . H3 H 0.0320 0.2223 0.1036 0.066 Uiso 1 1 calc R . . C4 C 0.3294(7) 0.1788(4) 0.14923(16) 0.0531(10) Uani 1 1 d . . . C5 C 0.3208(7) 0.0289(5) 0.15202(19) 0.0620(11) Uani 1 1 d . . . H5 H 0.1979 -0.0197 0.1348 0.074 Uiso 1 1 calc R . . C6 C 0.4910(8) -0.0469(5) 0.17974(19) 0.0668(12) Uani 1 1 d . . . H6 H 0.4829 -0.1462 0.1810 0.080 Uiso 1 1 calc R . . C7 C 0.6766(7) 0.0243(5) 0.20611(17) 0.0570(10) Uani 1 1 d . . . C8 C 0.6883(7) 0.1712(4) 0.20449(17) 0.0579(10) Uani 1 1 d . . . H8 H 0.8101 0.2197 0.2221 0.069 Uiso 1 1 calc R . . C9 C 0.5163(7) 0.2446(4) 0.17632(16) 0.0534(9) Uani 1 1 d . . . C10 C -0.1468(7) 0.4985(5) 0.06211(16) 0.0535(9) Uani 1 1 d . . . C11 C -0.1730(8) 0.7649(5) 0.05664(19) 0.0676(12) Uani 1 1 d . . . C12 C -0.3193(10) 0.8779(5) 0.0301(2) 0.0871(17) Uani 1 1 d . . . H12A H -0.2644 0.9703 0.0416 0.131 Uiso 1 1 calc R . . H12B H -0.4803 0.8662 0.0407 0.131 Uiso 1 1 calc R . . H12C H -0.3074 0.8701 -0.0091 0.131 Uiso 1 1 calc R . . O5 O 0.1479(6) 0.1529(3) 0.28767(16) 0.0765(10) Uani 1 1 d D . . H5OA H 0.275(6) 0.131(6) 0.304(2) 0.115 Uiso 1 1 d D . . H5OB H 0.073(9) 0.087(4) 0.272(2) 0.115 Uiso 1 1 d 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 S1 0.0546(7) 0.0655(7) 0.0711(7) 0.0015(5) -0.0264(5) -0.0061(5) O1 0.0501(16) 0.0518(16) 0.0665(17) -0.0010(12) -0.0226(13) -0.0025(12) O2 0.0630(19) 0.0550(17) 0.091(2) -0.0013(15) -0.0303(16) -0.0054(14) O3 0.0601(18) 0.0579(17) 0.088(2) 0.0067(15) -0.0251(16) 0.0040(14) O4 0.089(2) 0.063(2) 0.111(3) -0.0131(18) -0.056(2) 0.0042(17) N1 0.050(2) 0.054(2) 0.066(2) 0.0035(16) -0.0215(16) -0.0029(16) N2 0.051(2) 0.063(2) 0.062(2) 0.0040(16) -0.0228(16) 0.0025(16) C1 0.050(2) 0.060(3) 0.060(2) -0.0012(19) -0.0181(18) -0.0008(19) C2 0.044(2) 0.062(2) 0.054(2) -0.0012(18) -0.0150(17) -0.0062(18) C3 0.046(2) 0.063(2) 0.057(2) 0.0004(19) -0.0153(18) -0.0054(18) C4 0.045(2) 0.060(2) 0.054(2) -0.0017(18) -0.0123(17) -0.0036(18) C5 0.053(2) 0.057(2) 0.076(3) 0.003(2) -0.022(2) -0.0044(19) C6 0.060(3) 0.063(3) 0.077(3) 0.003(2) -0.015(2) -0.005(2) C7 0.047(2) 0.063(3) 0.061(2) 0.0077(19) -0.0122(18) 0.0023(18) C8 0.047(2) 0.066(3) 0.060(2) 0.0028(19) -0.0172(19) -0.0012(19) C9 0.046(2) 0.058(2) 0.056(2) 0.0000(18) -0.0102(17) -0.0035(17) C10 0.041(2) 0.066(2) 0.054(2) 0.0030(18) -0.0132(17) 0.0000(17) C11 0.066(3) 0.060(3) 0.076(3) -0.005(2) -0.024(2) 0.005(2) C12 0.093(4) 0.064(3) 0.103(4) -0.008(3) -0.042(3) 0.011(3) O5 0.067(2) 0.073(2) 0.089(2) 0.0047(17) -0.0307(17) 0.0065(17) _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 S1 C10 1.660(4) . ? O1 C1 1.359(5) . ? O1 C9 1.382(5) . ? O2 C1 1.207(5) . ? O3 C7 1.358(4) . ? O3 H3O 0.8200 . ? O4 C11 1.214(5) . ? N1 C10 1.332(5) . ? N1 C2 1.397(5) . ? N1 H1N 0.83(5) . ? N2 C10 1.387(5) . ? N2 C11 1.385(6) . ? N2 H2N 0.87(5) . ? C1 C2 1.463(5) . ? C2 C3 1.350(6) . ? C3 C4 1.429(5) . ? C3 H3 0.9300 . ? C4 C9 1.390(5) . ? C4 C5 1.405(6) . ? C5 C6 1.373(6) . ? C5 H5 0.9300 . ? C6 C7 1.399(6) . ? C6 H6 0.9300 . ? C7 C8 1.376(6) . ? C8 C9 1.374(5) . ? C8 H8 0.9300 . ? C11 C12 1.489(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? O5 H5OA 0.845(10) . ? O5 H5OB 0.845(10) . ? 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 C1 O1 C9 122.3(3) . . ? C7 O3 H3O 109.5 . . ? C10 N1 C2 131.0(4) . . ? C10 N1 H1N 114(3) . . ? C2 N1 H1N 115(3) . . ? C10 N2 C11 128.7(3) . . ? C10 N2 H2N 114(3) . . ? C11 N2 H2N 117(3) . . ? O2 C1 O1 117.1(3) . . ? O2 C1 C2 124.8(4) . . ? O1 C1 C2 118.1(4) . . ? C3 C2 N1 129.6(3) . . ? C3 C2 C1 120.0(4) . . ? N1 C2 C1 110.4(3) . . ? C2 C3 C4 120.4(4) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C9 C4 C5 116.5(4) . . ? C9 C4 C3 119.2(4) . . ? C5 C4 C3 124.3(4) . . ? C6 C5 C4 121.0(4) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 120.4(4) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? O3 C7 C8 119.2(4) . . ? O3 C7 C6 120.9(4) . . ? C8 C7 C6 119.9(4) . . ? C9 C8 C7 118.6(4) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C8 C9 O1 116.4(3) . . ? C8 C9 C4 123.6(4) . . ? O1 C9 C4 120.0(3) . . ? N1 C10 N2 114.8(4) . . ? N1 C10 S1 127.0(3) . . ? N2 C10 S1 118.2(3) . . ? O4 C11 N2 122.4(4) . . ? O4 C11 C12 123.4(4) . . ? N2 C11 C12 114.1(4) . . ? 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 . . ? H5OA O5 H5OB 118(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 68.16 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.299 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.080 # Attachment 'web_deposit_cif_file_1_KojiTsukamoto_1297836831.cif' data_et5 _database_code_depnum_ccdc_archive 'CCDC 803557' #TrackingRef 'web_deposit_cif_file_1_KojiTsukamoto_1297836831.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 N2 O3 S' _chemical_formula_sum 'C12 H12 N2 O3 S' _chemical_formula_weight 264.31 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' S S 0.3331 0.5567 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.9012(1) _cell_length_b 16.4201(3) _cell_length_c 9.3473(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.804(1) _cell_angle_gamma 90.00 _cell_volume 1211.25(4) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 12381 _cell_measurement_theta_min 9.47 _cell_measurement_theta_max 136.47 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 2.416 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.353 _exptl_absorpt_correction_T_max 0.718 _exptl_absorpt_process_details '(NUMABS; Higashi, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13375 _diffrn_reflns_av_R_equivalents 0.0851 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.39 _diffrn_reflns_theta_max 68.23 _reflns_number_total 2217 _reflns_number_gt 2030 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 2003)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson et al., 1996)' _computing_publication_material SHELXL-97 _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^)+(0.0546P)^2^+0.2697P] 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 SHELXL _refine_ls_extinction_coef 0.0266(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2217 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 S1 S 0.61358(5) 0.23506(2) 0.40177(5) 0.0433(2) Uani 1 1 d . . . O1 O 0.86994(16) -0.04404(9) 0.59176(16) 0.0604(4) Uani 1 1 d . . . O2 O 0.65404(13) -0.05561(7) 0.72827(12) 0.0406(3) Uani 1 1 d . . . O3 O 0.19722(16) -0.09216(8) 1.03300(15) 0.0524(4) Uani 1 1 d . . . H3O H 0.248(3) -0.1363(17) 1.052(3) 0.079 Uiso 1 1 d . . . N1 N 0.78481(18) 0.09937(8) 0.48504(16) 0.0411(4) Uani 1 1 d . . . H1N H 0.867(2) 0.0701(13) 0.476(2) 0.049 Uiso 1 1 d . . . N2 N 0.91388(18) 0.18004(8) 0.33069(16) 0.0406(4) Uani 1 1 d . . . H2N H 0.995(2) 0.1445(13) 0.343(2) 0.049 Uiso 1 1 d . . . C1 C 0.7404(2) -0.01334(10) 0.63259(18) 0.0400(4) Uani 1 1 d . . . C2 C 0.6761(2) 0.06526(9) 0.58240(18) 0.0363(4) Uani 1 1 d . . . C3 C 0.5305(2) 0.09441(10) 0.63279(19) 0.0415(4) Uani 1 1 d . . . H3 H 0.4889 0.1447 0.6018 0.050 Uiso 1 1 calc R . . C4 C 0.4406(2) 0.04792(9) 0.73376(18) 0.0385(4) Uani 1 1 d . . . C5 C 0.2884(2) 0.07231(11) 0.7916(2) 0.0513(5) Uani 1 1 d . . . H5 H 0.2404 0.1219 0.7635 0.062 Uiso 1 1 calc R . . C6 C 0.2085(2) 0.02497(11) 0.8885(2) 0.0513(5) Uani 1 1 d . . . H6 H 0.1071 0.0424 0.9248 0.062 Uiso 1 1 calc R . . C7 C 0.2792(2) -0.04928(10) 0.93272(19) 0.0403(4) Uani 1 1 d . . . C8 C 0.4283(2) -0.07606(9) 0.87724(18) 0.0373(4) Uani 1 1 d . . . H8 H 0.4757 -0.1258 0.9049 0.045 Uiso 1 1 calc R . . C9 C 0.50467(18) -0.02700(9) 0.77994(17) 0.0341(4) Uani 1 1 d . . . C10 C 0.7768(2) 0.16913(9) 0.40614(17) 0.0345(4) Uani 1 1 d . . . C11 C 0.9423(2) 0.24750(11) 0.2342(2) 0.0454(4) Uani 1 1 d . . . H11A H 0.9600 0.2973 0.2887 0.054 Uiso 1 1 calc R . . H11B H 0.8437 0.2549 0.1695 0.054 Uiso 1 1 calc R . . C12 C 1.0955(3) 0.22995(12) 0.1496(2) 0.0542(5) Uani 1 1 d . . . H12A H 1.1927 0.2227 0.2141 0.081 Uiso 1 1 calc R . . H12B H 1.1151 0.2747 0.0865 0.081 Uiso 1 1 calc R . . H12C H 1.0765 0.1812 0.0943 0.081 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 S1 0.0448(3) 0.0333(3) 0.0522(3) 0.00468(16) 0.0063(2) 0.00578(16) O1 0.0497(8) 0.0525(8) 0.0818(10) 0.0270(7) 0.0336(7) 0.0196(6) O2 0.0381(6) 0.0331(6) 0.0518(7) 0.0087(5) 0.0161(5) 0.0066(4) O3 0.0468(7) 0.0451(7) 0.0672(9) 0.0117(6) 0.0243(6) 0.0006(5) N1 0.0406(7) 0.0338(7) 0.0500(9) 0.0083(6) 0.0136(6) 0.0065(6) N2 0.0411(7) 0.0359(7) 0.0454(9) 0.0094(6) 0.0081(6) 0.0029(6) C1 0.0366(8) 0.0379(9) 0.0463(10) 0.0063(7) 0.0103(7) 0.0023(7) C2 0.0368(8) 0.0313(8) 0.0413(9) 0.0017(6) 0.0067(7) -0.0006(6) C3 0.0430(9) 0.0319(8) 0.0501(10) 0.0057(7) 0.0080(8) 0.0051(7) C4 0.0374(8) 0.0330(8) 0.0457(10) 0.0025(7) 0.0081(7) 0.0030(6) C5 0.0448(10) 0.0413(9) 0.0691(13) 0.0121(9) 0.0178(9) 0.0133(8) C6 0.0411(9) 0.0468(10) 0.0675(13) 0.0068(9) 0.0201(9) 0.0094(8) C7 0.0365(8) 0.0370(9) 0.0480(10) -0.0008(7) 0.0094(7) -0.0047(7) C8 0.0375(8) 0.0296(8) 0.0453(10) 0.0009(7) 0.0059(7) -0.0005(6) C9 0.0309(8) 0.0323(8) 0.0396(9) -0.0017(6) 0.0066(6) 0.0005(6) C10 0.0409(8) 0.0301(7) 0.0325(8) -0.0014(6) 0.0008(6) -0.0026(6) C11 0.0503(10) 0.0404(9) 0.0461(11) 0.0114(7) 0.0086(8) -0.0012(7) C12 0.0617(12) 0.0504(10) 0.0519(12) 0.0045(8) 0.0172(10) -0.0066(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 S1 C10 1.6829(16) . ? O1 C1 1.2189(19) . ? O2 C1 1.3443(19) . ? O2 C9 1.3793(17) . ? O3 C7 1.362(2) . ? O3 H3O 0.84(3) . ? N1 C10 1.362(2) . ? N1 C2 1.399(2) . ? N1 H1N 0.81(2) . ? N2 C10 1.333(2) . ? N2 C11 1.453(2) . ? N2 H2N 0.87(2) . ? C1 C2 1.456(2) . ? C2 C3 1.352(2) . ? C3 C4 1.429(2) . ? C3 H3 0.9300 . ? C4 C9 1.391(2) . ? C4 C5 1.401(2) . ? C5 C6 1.371(2) . ? C5 H5 0.9300 . ? C6 C7 1.395(2) . ? C6 H6 0.9300 . ? C7 C8 1.382(2) . ? C8 C9 1.376(2) . ? C8 H8 0.9300 . ? C11 C12 1.506(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C9 121.87(13) . . ? C7 O3 H3O 110.4(17) . . ? C10 N1 C2 132.49(14) . . ? C10 N1 H1N 116.9(14) . . ? C2 N1 H1N 110.6(14) . . ? C10 N2 C11 125.82(15) . . ? C10 N2 H2N 116.9(13) . . ? C11 N2 H2N 117.2(13) . . ? O1 C1 O2 117.13(15) . . ? O1 C1 C2 123.42(15) . . ? O2 C1 C2 119.44(13) . . ? C3 C2 N1 130.17(15) . . ? C3 C2 C1 119.40(14) . . ? N1 C2 C1 110.42(13) . . ? C2 C3 C4 119.98(15) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C9 C4 C5 116.05(15) . . ? C9 C4 C3 119.49(14) . . ? C5 C4 C3 124.46(15) . . ? C6 C5 C4 121.67(16) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C7 119.99(16) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? O3 C7 C8 122.47(15) . . ? O3 C7 C6 117.28(15) . . ? C8 C7 C6 120.24(15) . . ? C9 C8 C7 118.10(15) . . ? C9 C8 H8 121.0 . . ? C7 C8 H8 121.0 . . ? C8 C9 O2 116.26(14) . . ? C8 C9 C4 123.94(14) . . ? O2 C9 C4 119.80(14) . . ? N2 C10 N1 112.47(14) . . ? N2 C10 S1 122.84(12) . . ? N1 C10 S1 124.70(12) . . ? N2 C11 C12 109.43(15) . . ? N2 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? N2 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? 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 1.000 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.225 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.046 # Attachment 'web_deposit_cif_file_2_KojiTsukamoto_1297836831.cif' data_meac6 _database_code_depnum_ccdc_archive 'CCDC 803558' #TrackingRef 'web_deposit_cif_file_2_KojiTsukamoto_1297836831.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H12 N2 O4 S, H2 O' _chemical_formula_sum 'C13 H14 N2 O5 S' _chemical_formula_weight 310.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' S S 0.3331 0.5567 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4591(1) _cell_length_b 9.1454(2) _cell_length_c 11.2359(2) _cell_angle_alpha 92.042(1) _cell_angle_beta 106.960(1) _cell_angle_gamma 94.588(1) _cell_volume 729.39(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8045 _cell_measurement_theta_min 8.24 _cell_measurement_theta_max 136.47 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 2.197 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.452 _exptl_absorpt_correction_T_max 0.622 _exptl_absorpt_process_details '(NUMABS; Higashi, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8353 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 68.23 _reflns_number_total 2599 _reflns_number_gt 2359 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 2003)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson et al., 1996)' _computing_publication_material SHELXL-97 _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^)+(0.0924P)^2^+0.1014P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2599 _refine_ls_number_parameters 201 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1308 _refine_ls_wR_factor_gt 0.1278 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 S1 S -0.12399(6) 0.21495(5) -0.00529(4) 0.0571(2) Uani 1 1 d . . . O1 O 0.22304(17) 0.30331(13) 0.38102(11) 0.0536(3) Uani 1 1 d . . . O2 O 0.2019(2) 0.09308(14) 0.27438(13) 0.0672(4) Uani 1 1 d . . . O3 O 0.2846(3) 0.74329(17) 0.63181(14) 0.0793(5) Uani 1 1 d . . . H3O H 0.2510 0.6853 0.6769 0.119 Uiso 1 1 calc R . . O4 O 0.3006(3) 0.29688(18) -0.17928(17) 0.0866(5) Uani 1 1 d . . . O5 O 0.8166(3) 0.4266(2) 0.21106(19) 0.0941(6) Uani 1 1 d D . . H5A H 0.843(5) 0.382(4) 0.158(3) 0.141 Uiso 1 1 d D . . H5B H 0.768(6) 0.494(4) 0.177(3) 0.141 Uiso 1 1 d D . . N1 N 0.2489(2) 0.22896(17) 0.06276(13) 0.0533(4) Uani 1 1 d . . . N2 N 0.0931(2) 0.12712(16) -0.13709(13) 0.0516(4) Uani 1 1 d . . . H2N H -0.004(3) 0.062(2) -0.173(2) 0.062 Uiso 1 1 d . . . C1 C 0.2235(2) 0.22589(19) 0.27529(16) 0.0519(4) Uani 1 1 d . . . C2 C 0.2522(2) 0.3105(2) 0.17450(15) 0.0502(4) Uani 1 1 d . . . C3 C 0.2930(2) 0.4570(2) 0.18909(15) 0.0514(4) Uani 1 1 d . . . H3 H 0.3192 0.5080 0.1251 0.062 Uiso 1 1 calc R . . C4 C 0.2962(2) 0.53490(19) 0.30199(15) 0.0497(4) Uani 1 1 d . . . C5 C 0.3330(3) 0.6883(2) 0.32475(17) 0.0590(5) Uani 1 1 d . . . H5 H 0.3610 0.7452 0.2643 0.071 Uiso 1 1 calc R . . C6 C 0.3281(3) 0.7546(2) 0.43414(18) 0.0619(5) Uani 1 1 d . . . H6 H 0.3530 0.8561 0.4479 0.074 Uiso 1 1 calc R . . C7 C 0.2858(3) 0.6711(2) 0.52568(17) 0.0575(4) Uani 1 1 d . . . C8 C 0.2493(2) 0.5190(2) 0.50666(16) 0.0535(4) Uani 1 1 d . . . H8 H 0.2211 0.4626 0.5672 0.064 Uiso 1 1 calc R . . C9 C 0.2560(2) 0.45446(18) 0.39574(15) 0.0470(4) Uani 1 1 d . . . C10 C 0.0851(2) 0.19305(17) -0.02484(14) 0.0462(4) Uani 1 1 d . . . C11 C 0.1926(3) 0.1850(2) -0.21177(18) 0.0617(5) Uani 1 1 d . . . C12 C 0.1613(4) 0.1004(3) -0.3335(2) 0.0828(7) Uani 1 1 d . . . H12A H 0.1829 0.1657 -0.3940 0.124 Uiso 1 1 calc R . . H12B H 0.0341 0.0556 -0.3619 0.124 Uiso 1 1 calc R . . H12C H 0.2468 0.0255 -0.3230 0.124 Uiso 1 1 calc R . . C13 C 0.4259(3) 0.1701(3) 0.0627(2) 0.0788(7) Uani 1 1 d . . . H13A H 0.4005 0.0899 0.0008 0.118 Uiso 1 1 calc R . . H13B H 0.4848 0.1358 0.1433 0.118 Uiso 1 1 calc R . . H13C H 0.5083 0.2459 0.0440 0.118 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 S1 0.0486(3) 0.0736(4) 0.0500(3) -0.0068(2) 0.0161(2) 0.0103(2) O1 0.0622(7) 0.0484(7) 0.0492(6) -0.0041(5) 0.0173(5) -0.0006(5) O2 0.0836(9) 0.0487(7) 0.0638(8) -0.0061(6) 0.0161(7) 0.0001(6) O3 0.1100(12) 0.0655(9) 0.0607(8) -0.0198(7) 0.0264(8) 0.0047(8) O4 0.1079(12) 0.0681(9) 0.0997(12) -0.0025(8) 0.0622(10) -0.0141(8) O5 0.1193(15) 0.0883(13) 0.0906(12) -0.0140(9) 0.0579(12) 0.0102(10) N1 0.0472(8) 0.0597(9) 0.0536(8) -0.0115(6) 0.0173(6) 0.0070(6) N2 0.0610(8) 0.0507(8) 0.0465(7) -0.0054(6) 0.0234(6) 0.0014(6) C1 0.0496(9) 0.0513(10) 0.0506(9) -0.0067(7) 0.0101(7) 0.0018(7) C2 0.0452(8) 0.0555(10) 0.0485(8) -0.0073(7) 0.0127(7) 0.0053(7) C3 0.0497(9) 0.0559(10) 0.0477(8) -0.0022(7) 0.0142(7) 0.0029(7) C4 0.0466(8) 0.0516(9) 0.0472(8) -0.0032(7) 0.0093(7) 0.0031(7) C5 0.0659(11) 0.0519(10) 0.0533(9) 0.0010(8) 0.0100(8) 0.0005(8) C6 0.0689(11) 0.0477(9) 0.0606(10) -0.0064(8) 0.0077(9) 0.0034(8) C7 0.0569(10) 0.0595(11) 0.0508(9) -0.0123(8) 0.0085(8) 0.0087(8) C8 0.0523(9) 0.0588(10) 0.0475(8) -0.0050(7) 0.0132(7) 0.0033(7) C9 0.0412(8) 0.0478(9) 0.0480(8) -0.0052(7) 0.0086(6) 0.0023(6) C10 0.0536(9) 0.0432(8) 0.0443(8) -0.0008(6) 0.0188(7) 0.0042(6) C11 0.0756(12) 0.0569(11) 0.0633(11) 0.0027(8) 0.0370(9) 0.0076(9) C12 0.1085(18) 0.0906(16) 0.0642(12) -0.0041(11) 0.0502(12) 0.0085(13) C13 0.0529(11) 0.0992(17) 0.0824(14) -0.0270(12) 0.0175(10) 0.0199(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 S1 C10 1.6635(16) . ? O1 C1 1.362(2) . ? O1 C9 1.380(2) . ? O2 C1 1.212(2) . ? O3 C7 1.345(2) . ? O3 H3O 0.8200 . ? O4 C11 1.224(2) . ? O5 H5A 0.78(3) . ? O5 H5B 0.80(3) . ? N1 C10 1.334(2) . ? N1 C2 1.430(2) . ? N1 C13 1.465(2) . ? N2 C11 1.367(2) . ? N2 C10 1.398(2) . ? N2 H2N 0.89(2) . ? C1 C2 1.450(3) . ? C2 C3 1.344(2) . ? C3 C4 1.425(2) . ? C3 H3 0.9300 . ? C4 C9 1.394(2) . ? C4 C5 1.408(2) . ? C5 C6 1.362(3) . ? C5 H5 0.9300 . ? C6 C7 1.395(3) . ? C6 H6 0.9300 . ? C7 C8 1.392(3) . ? C8 C9 1.376(2) . ? C8 H8 0.9300 . ? C11 C12 1.495(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C9 122.61(13) . . ? C7 O3 H3O 109.5 . . ? H5A O5 H5B 103(4) . . ? C10 N1 C2 119.58(14) . . ? C10 N1 C13 124.00(15) . . ? C2 N1 C13 115.64(14) . . ? C11 N2 C10 125.53(15) . . ? C11 N2 H2N 116.8(14) . . ? C10 N2 H2N 113.8(14) . . ? O2 C1 O1 117.23(16) . . ? O2 C1 C2 125.99(16) . . ? O1 C1 C2 116.77(15) . . ? C3 C2 N1 121.88(16) . . ? C3 C2 C1 121.34(15) . . ? N1 C2 C1 116.61(15) . . ? C2 C3 C4 120.48(16) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C9 C4 C5 117.40(16) . . ? C9 C4 C3 118.01(15) . . ? C5 C4 C3 124.58(16) . . ? C6 C5 C4 120.83(17) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 120.37(17) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? O3 C7 C8 122.24(17) . . ? O3 C7 C6 117.33(17) . . ? C8 C7 C6 120.43(16) . . ? C9 C8 C7 118.17(16) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C8 C9 O1 116.66(15) . . ? C8 C9 C4 122.80(16) . . ? O1 C9 C4 120.53(15) . . ? N1 C10 N2 116.81(14) . . ? N1 C10 S1 124.03(12) . . ? N2 C10 S1 119.10(12) . . ? O4 C11 N2 121.75(17) . . ? O4 C11 C12 123.26(18) . . ? N2 C11 C12 114.98(17) . . ? 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 . . ? N1 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.265 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.066 # Attachment 'web_deposit_cif_file_3_KojiTsukamoto_1297836831.cif' data_urea7 _database_code_depnum_ccdc_archive 'CCDC 803559' #TrackingRef 'web_deposit_cif_file_3_KojiTsukamoto_1297836831.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 O5, C3 H7 N O' _chemical_formula_sum 'C15 H17 N3 O6' _chemical_formula_weight 335.32 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 6.2937(7) _cell_length_b 18.5171(21) _cell_length_c 13.7626(16) _cell_angle_alpha 90.00 _cell_angle_beta 101.902(6) _cell_angle_gamma 90.00 _cell_volume 1569.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 7752 _cell_measurement_theta_min 6.56 _cell_measurement_theta_max 136.93 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.944 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.685 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_process_details '(NUMABS; Higashi, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17529 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.06 _diffrn_reflns_theta_max 68.24 _reflns_number_total 2875 _reflns_number_gt 1920 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO (Rigaku, 2003)' _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2004)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson et al., 1996)' _computing_publication_material SHELXL-97 _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^)+(0.0730P)^2^+0.0465P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2875 _refine_ls_number_parameters 274 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.080 _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 0.86698(19) 0.22634(6) 0.72418(10) 0.0596(4) Uani 1 1 d . . . O2 O 0.7206(2) 0.32399(7) 0.77451(11) 0.0695(4) Uani 1 1 d . . . O3 O 1.2049(2) 0.02806(7) 0.60813(12) 0.0821(5) Uani 1 1 d . . . H3O H 1.1989 -0.0161 0.6047 0.123 Uiso 1 1 calc R . . O4 O 0.2724(2) 0.16069(7) 0.92649(11) 0.0737(4) Uani 1 1 d . . . O5 O 0.2890(2) 0.38128(7) 0.89472(11) 0.0752(5) Uani 1 1 d . . . N1 N 0.4334(2) 0.25201(9) 0.85651(12) 0.0600(4) Uani 1 1 d . . . H1N H 0.443(3) 0.3017(11) 0.8592(15) 0.072 Uiso 1 1 d . . . N2 N 0.1722(3) 0.27621(8) 0.94993(12) 0.0583(4) Uani 1 1 d . . . H2N H 0.077(3) 0.2589(11) 0.9856(15) 0.070 Uiso 1 1 d . . . C1 C 0.7203(3) 0.25888(10) 0.77027(14) 0.0545(5) Uani 1 1 d . . . C2 C 0.5745(3) 0.21196(10) 0.81148(14) 0.0538(5) Uani 1 1 d . . . C3 C 0.5842(3) 0.14007(10) 0.80231(14) 0.0575(5) Uani 1 1 d . . . H3 H 0.4888 0.1109 0.8281 0.069 Uiso 1 1 calc R . . C4 C 0.7391(3) 0.10786(9) 0.75343(14) 0.0522(4) Uani 1 1 d . . . C5 C 0.7609(3) 0.03361(9) 0.73993(15) 0.0613(5) Uani 1 1 d . . . H5 H 0.6690 0.0021 0.7640 0.074 Uiso 1 1 calc R . . C6 C 0.9133(3) 0.00589(10) 0.69237(15) 0.0615(5) Uani 1 1 d . . . H6 H 0.9247 -0.0438 0.6848 0.074 Uiso 1 1 calc R . . C7 C 1.0514(3) 0.05250(10) 0.65526(15) 0.0588(5) Uani 1 1 d . . . C8 C 1.0335(3) 0.12642(10) 0.66609(15) 0.0591(5) Uani 1 1 d . . . H8 H 1.1238 0.1579 0.6408 0.071 Uiso 1 1 calc R . . C9 C 0.8798(3) 0.15234(9) 0.71484(14) 0.0522(4) Uani 1 1 d . . . C10 C 0.2965(3) 0.22477(10) 0.91085(14) 0.0557(5) Uani 1 1 d . . . C11 C 0.1687(3) 0.34914(10) 0.94033(14) 0.0589(5) Uani 1 1 d . . . C12 C 0.0090(3) 0.38812(10) 0.98707(17) 0.0672(6) Uani 1 1 d . . . H12A H 0.0767 0.4299 1.0215 0.101 Uiso 1 1 calc R . . H12B H -0.0406 0.3567 1.0333 0.101 Uiso 1 1 calc R . . H12C H -0.1124 0.4029 0.9366 0.101 Uiso 1 1 calc R . . N3A N 0.246(2) 0.3780(3) 0.5925(13) 0.063(2) Uani 0.720(5) 1 d PDU A 1 O6A O 0.3674(15) 0.2656(3) 0.5692(9) 0.0801(13) Uani 0.720(5) 1 d PDU A 1 C13A C 0.2441(5) 0.30822(16) 0.5992(2) 0.0675(9) Uani 0.720(5) 1 d PDU A 1 H13A H 0.1393 0.2881 0.6297 0.081 Uiso 0.720(5) 1 calc PR A 1 C14A C 0.0930(6) 0.4227(2) 0.6318(3) 0.0871(12) Uani 0.720(5) 1 d PDU A 1 H14A H -0.0015 0.4470 0.5782 0.131 Uiso 0.720(5) 1 calc PR A 1 H14B H 0.1714 0.4577 0.6768 0.131 Uiso 0.720(5) 1 calc PR A 1 H14C H 0.0084 0.3928 0.6665 0.131 Uiso 0.720(5) 1 calc PR A 1 C15A C 0.4083(6) 0.41391(19) 0.5479(3) 0.0834(11) Uani 0.720(5) 1 d PDU A 1 H15A H 0.4751 0.4521 0.5908 0.125 Uiso 0.720(5) 1 calc PR A 1 H15B H 0.3400 0.4337 0.4847 0.125 Uiso 0.720(5) 1 calc PR A 1 H15C H 0.5170 0.3796 0.5389 0.125 Uiso 0.720(5) 1 calc PR A 1 N3B N 0.264(7) 0.3892(8) 0.594(3) 0.074(5) Uani 0.280(5) 1 d PDU A 2 O6B O 0.386(5) 0.2804(9) 0.559(3) 0.118(8) Uani 0.280(5) 1 d PDU A 2 C13B C 0.3763(14) 0.3469(6) 0.5495(7) 0.087(3) Uani 0.280(5) 1 d PDU A 2 H13B H 0.4561 0.3679 0.5071 0.104 Uiso 0.280(5) 1 calc PR A 2 C14B C 0.1090(16) 0.3597(8) 0.6477(8) 0.106(4) Uani 0.280(5) 1 d PDU A 2 H14D H 0.1201 0.3080 0.6491 0.159 Uiso 0.280(5) 1 calc PR A 2 H14E H -0.0352 0.3735 0.6152 0.159 Uiso 0.280(5) 1 calc PR A 2 H14F H 0.1392 0.3780 0.7144 0.159 Uiso 0.280(5) 1 calc PR A 2 C15B C 0.234(2) 0.4641(6) 0.5652(10) 0.144(5) Uani 0.280(5) 1 d PDU A 2 H15D H 0.3505 0.4791 0.5342 0.216 Uiso 0.280(5) 1 calc PR A 2 H15E H 0.2347 0.4933 0.6229 0.216 Uiso 0.280(5) 1 calc PR A 2 H15F H 0.0982 0.4698 0.5192 0.216 Uiso 0.280(5) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0579(7) 0.0453(7) 0.0839(9) -0.0045(6) 0.0339(7) -0.0046(5) O2 0.0734(9) 0.0477(7) 0.0960(10) -0.0081(7) 0.0373(8) -0.0052(6) O3 0.0785(9) 0.0570(8) 0.1299(14) -0.0064(7) 0.0658(9) 0.0006(6) O4 0.0861(10) 0.0573(9) 0.0907(11) 0.0039(7) 0.0483(8) 0.0053(7) O5 0.0863(10) 0.0544(8) 0.1005(11) 0.0005(7) 0.0552(9) -0.0033(7) N1 0.0624(9) 0.0506(9) 0.0760(11) -0.0019(8) 0.0349(8) 0.0023(7) N2 0.0641(10) 0.0515(9) 0.0682(11) 0.0000(7) 0.0343(8) 0.0020(7) C1 0.0514(10) 0.0492(10) 0.0676(12) -0.0045(9) 0.0230(9) -0.0009(8) C2 0.0502(10) 0.0543(10) 0.0615(11) 0.0004(8) 0.0223(8) 0.0009(8) C3 0.0577(11) 0.0521(10) 0.0701(12) 0.0017(9) 0.0304(9) -0.0023(8) C4 0.0502(10) 0.0492(9) 0.0619(11) 0.0007(8) 0.0226(9) -0.0005(7) C5 0.0628(11) 0.0478(10) 0.0811(14) 0.0035(9) 0.0333(10) -0.0041(8) C6 0.0625(11) 0.0482(10) 0.0810(14) -0.0013(9) 0.0312(10) 0.0004(8) C7 0.0536(10) 0.0525(10) 0.0773(13) -0.0021(9) 0.0298(10) 0.0009(8) C8 0.0535(10) 0.0522(10) 0.0789(13) -0.0025(9) 0.0304(10) -0.0050(8) C9 0.0506(10) 0.0438(9) 0.0655(12) -0.0039(8) 0.0195(9) -0.0023(7) C10 0.0584(11) 0.0523(10) 0.0621(12) 0.0006(9) 0.0255(9) 0.0026(8) C11 0.0637(11) 0.0550(10) 0.0630(12) -0.0039(9) 0.0245(10) -0.0011(9) C12 0.0695(12) 0.0595(11) 0.0799(14) -0.0069(10) 0.0322(11) 0.0076(9) N3A 0.063(4) 0.056(2) 0.079(4) -0.002(3) 0.033(4) 0.003(2) O6A 0.088(2) 0.067(2) 0.097(3) -0.003(2) 0.045(2) 0.0112(18) C13A 0.0665(18) 0.0637(18) 0.083(2) -0.0006(14) 0.0400(16) -0.0014(13) C14A 0.085(2) 0.072(2) 0.115(3) -0.011(2) 0.045(2) 0.0110(18) C15A 0.095(2) 0.073(2) 0.094(3) -0.0064(17) 0.047(2) -0.0193(18) N3B 0.070(9) 0.074(7) 0.080(11) -0.013(8) 0.019(6) -0.011(7) O6B 0.151(15) 0.091(7) 0.128(12) 0.004(9) 0.064(9) 0.029(9) C13B 0.082(6) 0.092(6) 0.096(7) 0.006(5) 0.042(5) -0.008(5) C14B 0.088(6) 0.153(10) 0.089(7) -0.008(7) 0.045(5) -0.004(7) C15B 0.201(15) 0.084(6) 0.144(11) 0.005(6) 0.027(10) 0.013(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.363(2) . ? O1 C9 1.3801(19) . ? O2 C1 1.207(2) . ? O3 C7 1.348(2) . ? O3 H3O 0.8200 . ? O4 C10 1.221(2) . ? O5 C11 1.232(2) . ? N1 C10 1.350(2) . ? N1 C2 1.397(2) . ? N1 H1N 0.92(2) . ? N2 C11 1.357(2) . ? N2 C10 1.408(2) . ? N2 H2N 0.91(2) . ? C1 C2 1.460(2) . ? C2 C3 1.340(2) . ? C3 C4 1.425(2) . ? C3 H3 0.9300 . ? C4 C9 1.393(2) . ? C4 C5 1.398(2) . ? C5 C6 1.368(2) . ? C5 H5 0.9300 . ? C6 C7 1.394(3) . ? C6 H6 0.9300 . ? C7 C8 1.384(2) . ? C8 C9 1.372(2) . ? C8 H8 0.9300 . ? C11 C12 1.487(2) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? N3A C13A 1.295(6) . ? N3A C14A 1.454(5) . ? N3A C15A 1.458(7) . ? O6A C13A 1.236(8) . ? C13A H13A 0.9300 . ? C14A H14A 0.9600 . ? C14A H14B 0.9600 . ? C14A H14C 0.9600 . ? C15A H15A 0.9600 . ? C15A H15B 0.9600 . ? C15A H15C 0.9600 . ? N3B C13B 1.293(14) . ? N3B C15B 1.444(16) . ? N3B C14B 1.445(15) . ? O6B C13B 1.238(16) . ? C13B H13B 0.9300 . ? C14B H14D 0.9600 . ? C14B H14E 0.9600 . ? C14B H14F 0.9600 . ? C15B H15D 0.9600 . ? C15B H15E 0.9600 . ? C15B H15F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C9 122.71(13) . . ? C7 O3 H3O 109.5 . . ? C10 N1 C2 125.78(17) . . ? C10 N1 H1N 113.4(13) . . ? C2 N1 H1N 120.2(13) . . ? C11 N2 C10 129.45(16) . . ? C11 N2 H2N 113.9(13) . . ? C10 N2 H2N 116.6(13) . . ? O2 C1 O1 118.00(16) . . ? O2 C1 C2 124.77(16) . . ? O1 C1 C2 117.23(15) . . ? C3 C2 N1 127.93(17) . . ? C3 C2 C1 120.68(16) . . ? N1 C2 C1 111.38(16) . . ? C2 C3 C4 120.61(16) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C9 C4 C5 116.32(16) . . ? C9 C4 C3 118.92(16) . . ? C5 C4 C3 124.75(16) . . ? C6 C5 C4 122.04(16) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C7 119.65(17) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? O3 C7 C8 117.79(16) . . ? O3 C7 C6 122.09(17) . . ? C8 C7 C6 120.12(16) . . ? C9 C8 C7 118.68(16) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C8 C9 O1 116.97(15) . . ? C8 C9 C4 123.18(16) . . ? O1 C9 C4 119.84(14) . . ? O4 C10 N1 125.28(17) . . ? O4 C10 N2 119.42(16) . . ? N1 C10 N2 115.30(16) . . ? O5 C11 N2 122.09(16) . . ? O5 C11 C12 121.82(18) . . ? N2 C11 C12 116.09(17) . . ? 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 . . ? C13A N3A C14A 121.8(5) . . ? C13A N3A C15A 120.0(4) . . ? C14A N3A C15A 118.2(5) . . ? O6A C13A N3A 126.9(6) . . ? O6A C13A H13A 116.6 . . ? N3A C13A H13A 116.6 . . ? C13B N3B C15B 120.2(16) . . ? C13B N3B C14B 120.4(14) . . ? C15B N3B C14B 116.2(16) . . ? O6B C13B N3B 124.8(18) . . ? O6B C13B H13B 117.6 . . ? N3B C13B H13B 117.6 . . ? N3B C14B H14D 109.5 . . ? N3B C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? N3B C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 109.5 . . ? N3B C15B H15D 109.5 . . ? N3B C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? N3B C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.177 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.056