# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Baiwang Sun' _publ_contact_author_email chmsunbw@seu.edu.cn loop_ _publ_author_name 'Yang-Hui Luo' 'Chen-Guang Zhang' 'Bing Xu' 'Baiwang Sun' data_lyh1 _database_code_depnum_ccdc_archive 'CCDC 877952' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O3, 0.5(C6 H8 N2)' _chemical_formula_sum 'C10 H10 N O3' _chemical_formula_weight 192.19 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.875(4) _cell_length_b 13.254(3) _cell_length_c 14.054(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.04(4) _cell_angle_gamma 90.000 _cell_volume 1914.9(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1568 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 24.41 _exptl_crystal_description block _exptl_crystal_colour White _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCXmini diffractometer' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count 2 _diffrn_standards_interval_time 150 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7386 _diffrn_reflns_av_R_equivalents 0.1690 _diffrn_reflns_av_sigmaI/netI 0.1080 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 24.41 _reflns_number_total 1570 _reflns_number_gt 704 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0849P)^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 1568 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1779 _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.2005 _refine_ls_wR_factor_gt 0.1543 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.1972(3) 0.1307(2) 0.0217(2) 0.0890(12) Uani 1 1 d . . . O2 O 0.1894(3) -0.0353(2) 0.0510(2) 0.0748(10) Uani 1 1 d . . . H2 H 0.1535 -0.0370 -0.0101 0.112 Uiso 1 1 calc R . . O3 O 0.2988(4) 0.2531(2) 0.1729(2) 0.0977(13) Uani 1 1 d . . . H3 H 0.2728 0.2375 0.1132 0.147 Uiso 1 1 calc R . . C1 C 0.4015(5) 0.0978(4) 0.3935(3) 0.0828(15) Uani 1 1 d . . . H1 H 0.4403 0.1065 0.4625 0.099 Uiso 1 1 calc R . . C2 C 0.3686(5) 0.0014(4) 0.3561(3) 0.0831(16) Uani 1 1 d . . . H2A H 0.3850 -0.0538 0.3993 0.100 Uiso 1 1 calc R . . C3 C 0.3112(4) -0.0112(3) 0.2544(3) 0.0671(13) Uani 1 1 d . . . H3A H 0.2879 -0.0755 0.2283 0.081 Uiso 1 1 calc R . . C4 C 0.2874(4) 0.0720(3) 0.1895(3) 0.0528(11) Uani 1 1 d . . . C5 C 0.3214(4) 0.1690(3) 0.2295(3) 0.0651(13) Uani 1 1 d . . . C6 C 0.3790(5) 0.1807(4) 0.3324(3) 0.0787(15) Uani 1 1 d . . . H6 H 0.4022 0.2446 0.3598 0.094 Uiso 1 1 calc R . . C7 C 0.2209(5) 0.0596(3) 0.0799(3) 0.0621(13) Uani 1 1 d . . . N1 N 0.0585(3) 0.0500(2) 0.3532(2) 0.0551(10) Uani 1 1 d . . . C8 C 0.0596(5) 0.2336(3) 0.3633(3) 0.0812(16) Uani 1 1 d . . . H8A H 0.0913 0.2173 0.4337 0.122 Uiso 1 1 calc R . . H8B H -0.0177 0.2739 0.3493 0.122 Uiso 1 1 calc R . . H8C H 0.1248 0.2707 0.3457 0.122 Uiso 1 1 calc R . . C9 C 0.0286(4) 0.1377(3) 0.3025(3) 0.0522(11) Uani 1 1 d . . . C12 C 0.0301(4) -0.0353(3) 0.3016(3) 0.0651(13) Uani 1 1 d . . . H12 H 0.0509 -0.0965 0.3355 0.078 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 0.139(3) 0.061(2) 0.0525(18) 0.0031(17) 0.012(2) -0.008(2) O2 0.109(3) 0.0555(19) 0.0488(18) -0.0097(14) 0.0102(19) -0.0031(18) O3 0.156(4) 0.058(2) 0.069(2) -0.0017(17) 0.024(3) -0.024(2) C1 0.077(4) 0.108(4) 0.047(3) -0.012(3) -0.003(3) -0.003(3) C2 0.098(4) 0.081(4) 0.055(3) 0.002(3) 0.005(3) 0.019(3) C3 0.080(3) 0.061(3) 0.058(3) 0.001(2) 0.019(3) 0.013(3) C4 0.055(3) 0.057(3) 0.044(2) -0.002(2) 0.011(2) 0.002(2) C5 0.079(4) 0.056(3) 0.056(3) -0.001(2) 0.016(3) -0.010(3) C6 0.094(4) 0.075(3) 0.058(3) -0.012(3) 0.012(3) -0.016(3) C7 0.077(3) 0.054(3) 0.052(3) -0.006(2) 0.018(3) 0.002(2) N1 0.063(2) 0.045(2) 0.050(2) -0.0015(17) 0.0081(19) 0.0054(19) C8 0.118(5) 0.055(3) 0.063(3) -0.008(2) 0.018(3) 0.006(3) C9 0.055(3) 0.045(2) 0.057(2) -0.001(2) 0.020(2) 0.004(2) C12 0.075(4) 0.042(2) 0.068(3) 0.006(2) 0.011(3) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.219(5) . ? O2 C7 1.332(4) . ? O2 H2 0.8200 . ? O3 C5 1.344(5) . ? O3 H3 0.8200 . ? C1 C6 1.366(6) . ? C1 C2 1.383(6) . ? C1 H1 0.9300 . ? C2 C3 1.371(5) . ? C2 H2A 0.9300 . ? C3 C4 1.400(5) . ? C3 H3A 0.9300 . ? C4 C5 1.404(5) . ? C4 C7 1.482(6) . ? C5 C6 1.384(6) . ? C6 H6 0.9300 . ? N1 C9 1.347(4) . ? N1 C12 1.324(4) . ? C8 C9 1.507(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C9 1.403(7) 2 ? C12 C12 1.384(8) 2 ? C12 H12 0.9300 . ? 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 O2 H2 109.5 . . ? C5 O3 H3 109.5 . . ? C6 C1 C2 122.2(4) . . ? C6 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 118.8(5) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C2 C3 C4 120.5(5) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 119.5(4) . . ? C5 C4 C7 119.6(4) . . ? C3 C4 C7 120.9(4) . . ? O3 C5 C6 117.3(4) . . ? O3 C5 C4 123.3(4) . . ? C6 C5 C4 119.4(4) . . ? C1 C6 C5 119.6(5) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? O1 C7 O2 123.3(4) . . ? O1 C7 C4 122.4(4) . . ? O2 C7 C4 114.3(4) . . ? C9 N1 C12 118.3(3) . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C9 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C9 120.3(2) . 2 ? N1 C9 C8 117.2(3) . . ? C9 C9 C8 122.5(2) 2 . ? N1 C12 C12 121.4(2) . 2 ? N1 C12 H12 119.3 . . ? C12 C12 H12 119.3 2 . ? 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 C6 C1 C2 C3 -0.1(8) . . . . ? C1 C2 C3 C4 0.5(7) . . . . ? C2 C3 C4 C5 -0.7(7) . . . . ? C2 C3 C4 C7 -177.7(4) . . . . ? C3 C4 C5 O3 -178.2(4) . . . . ? C7 C4 C5 O3 -1.2(7) . . . . ? C3 C4 C5 C6 0.6(7) . . . . ? C7 C4 C5 C6 177.6(4) . . . . ? C2 C1 C6 C5 -0.1(8) . . . . ? O3 C5 C6 C1 178.7(5) . . . . ? C4 C5 C6 C1 -0.2(7) . . . . ? C5 C4 C7 O1 2.0(7) . . . . ? C3 C4 C7 O1 179.0(4) . . . . ? C5 C4 C7 O2 -177.8(4) . . . . ? C3 C4 C7 O2 -0.8(6) . . . . ? C12 N1 C9 C9 -1.4(7) . . . 2 ? C12 N1 C9 C8 178.8(4) . . . . ? C9 N1 C12 C12 -0.6(8) . . . 2 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.41 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.210 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.067 # Attachment '- 3.cif' data_lyh3 _database_code_depnum_ccdc_archive 'CCDC 877953' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O3, C6 H8 N2, H2 O' _chemical_formula_sum 'C13 H16 N2 O4' _chemical_formula_weight 264.28 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 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 7.2391(14) _cell_length_b 8.0130(16) _cell_length_c 13.094(3) _cell_angle_alpha 106.01(3) _cell_angle_beta 102.96(3) _cell_angle_gamma 94.23(3) _cell_volume 704.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1738 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour White _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCXmini diffractometer' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count 2 _diffrn_standards_interval_time 150 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5971 _diffrn_reflns_av_R_equivalents 0.1658 _diffrn_reflns_av_sigmaI/netI 0.2360 _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 -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2478 _reflns_number_gt 1738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1293P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2478 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1462 _refine_ls_R_factor_gt 0.0881 _refine_ls_wR_factor_ref 0.2523 _refine_ls_wR_factor_gt 0.2044 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 1.1066(6) 0.2180(7) 0.1089(4) 0.0761(16) Uani 1 1 d . . . O2 O 1.1870(6) 0.3750(7) 0.2900(4) 0.0768(16) Uani 1 1 d . . . H2 H 1.2911 0.3986 0.2785 0.115 Uiso 1 1 calc R . . N1 N 0.8395(7) 0.6055(7) 0.1839(5) 0.0585(16) Uani 1 1 d . . . O3 O 0.3750(6) -0.0206(6) 0.2718(4) 0.0843(17) Uani 1 1 d . . . H3A H 0.3054 -0.0906 0.2157 0.126 Uiso 1 1 calc R . . C2 C 0.8914(9) 0.1767(9) 0.2223(6) 0.0547(18) Uani 1 1 d . . . C11 C 0.6512(10) 0.6330(9) 0.3172(6) 0.0606(19) Uani 1 1 d . . . C9 C 0.8222(9) 0.6748(9) 0.2862(5) 0.0560(18) Uani 1 1 d . . . N2 N 0.5061(7) 0.5161(8) 0.2438(5) 0.0631(17) Uani 1 1 d . . . C5 C 0.6726(10) 0.1695(10) 0.3378(6) 0.073(2) Uani 1 1 d . . . H5A H 0.6440 0.2080 0.4055 0.087 Uiso 1 1 calc R . . C3 C 0.7600(9) 0.0483(9) 0.1335(6) 0.062(2) Uani 1 1 d . . . H3B H 0.7871 0.0103 0.0654 0.074 Uiso 1 1 calc R . . C7 C 0.5877(9) -0.0212(9) 0.1499(6) 0.068(2) Uani 1 1 d . . . H7A H 0.5035 -0.1091 0.0931 0.081 Uiso 1 1 calc R . . C6 C 0.5435(9) 0.0401(9) 0.2494(6) 0.062(2) Uani 1 1 d . . . C4 C 0.8461(8) 0.2399(9) 0.3224(6) 0.058(2) Uani 1 1 d . . . H4A H 0.9297 0.3282 0.3792 0.069 Uiso 1 1 calc R . . C10 C 0.9973(10) 0.8036(10) 0.3649(6) 0.085(2) Uani 1 1 d . . . H10A H 1.0953 0.8114 0.3270 0.128 Uiso 1 1 calc R . . H10B H 1.0456 0.7624 0.4266 0.128 Uiso 1 1 calc R . . H10C H 0.9603 0.9174 0.3902 0.128 Uiso 1 1 calc R . . C14 C 0.6911(9) 0.4870(9) 0.1111(6) 0.063(2) Uani 1 1 d . . . H14A H 0.6991 0.4349 0.0397 0.076 Uiso 1 1 calc R . . C1 C 1.0708(9) 0.2600(9) 0.1988(7) 0.060(2) Uani 1 1 d . . . C13 C 0.5258(9) 0.4429(9) 0.1433(6) 0.066(2) Uani 1 1 d . . . H13A H 0.4272 0.3601 0.0926 0.079 Uiso 1 1 calc R . . C12 C 0.6285(10) 0.7101(11) 0.4326(6) 0.088(3) Uani 1 1 d . . . H12A H 0.5039 0.6661 0.4362 0.132 Uiso 1 1 calc R . . H12B H 0.6423 0.8357 0.4506 0.132 Uiso 1 1 calc R . . H12C H 0.7249 0.6773 0.4839 0.132 Uiso 1 1 calc R . . O4 O 0.1306(8) 0.7456(8) 0.0971(6) 0.0798(18) Uani 1 1 d . . . H1 H 0.029(13) 0.689(12) 0.125(7) 0.14(3) Uiso 1 1 d . . . H1B H 0.057(9) 0.745(9) 0.044(5) 0.05(3) 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 0.063(3) 0.083(4) 0.076(4) 0.009(3) 0.030(3) -0.014(3) O2 0.051(3) 0.095(4) 0.073(4) 0.012(3) 0.022(3) -0.022(3) N1 0.051(4) 0.051(4) 0.073(4) 0.015(3) 0.024(3) -0.006(3) O3 0.053(3) 0.096(4) 0.099(4) 0.020(3) 0.033(3) -0.021(3) C2 0.044(4) 0.060(5) 0.064(5) 0.023(4) 0.018(3) 0.002(3) C11 0.050(5) 0.064(5) 0.066(5) 0.018(4) 0.016(4) 0.000(4) C9 0.053(4) 0.057(5) 0.055(5) 0.013(4) 0.015(3) -0.004(4) N2 0.050(4) 0.073(4) 0.059(4) 0.015(3) 0.015(3) -0.016(3) C5 0.066(5) 0.094(6) 0.059(5) 0.014(5) 0.032(4) -0.006(4) C3 0.053(4) 0.071(5) 0.059(5) 0.015(4) 0.021(4) -0.016(4) C7 0.066(5) 0.063(5) 0.068(5) 0.008(4) 0.026(4) -0.005(4) C6 0.046(4) 0.064(5) 0.072(5) 0.021(4) 0.012(4) -0.009(4) C4 0.045(4) 0.064(5) 0.064(5) 0.021(4) 0.017(3) -0.007(3) C10 0.078(6) 0.076(6) 0.087(6) 0.013(5) 0.019(5) -0.024(5) C14 0.055(5) 0.067(5) 0.055(5) 0.002(4) 0.013(4) -0.011(4) C1 0.045(5) 0.054(5) 0.084(6) 0.024(5) 0.019(4) -0.002(4) C13 0.047(4) 0.064(5) 0.083(6) 0.023(5) 0.013(4) -0.008(3) C12 0.081(6) 0.100(7) 0.077(6) 0.012(5) 0.035(4) -0.009(5) O4 0.056(4) 0.100(5) 0.081(4) 0.027(4) 0.023(3) -0.013(3) _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 1.223(7) . ? O2 C1 1.346(8) . ? O2 H2 0.8200 . ? N1 C9 1.339(7) . ? N1 C14 1.362(7) . ? O3 C6 1.401(7) . ? O3 H3A 0.8200 . ? C2 C4 1.390(8) . ? C2 C3 1.419(9) . ? C2 C1 1.547(9) . ? C11 N2 1.345(8) . ? C11 C9 1.432(8) . ? C11 C12 1.517(9) . ? C9 C10 1.539(9) . ? N2 C13 1.330(8) . ? C5 C6 1.414(9) . ? C5 C4 1.417(8) . ? C5 H5A 0.9300 . ? C3 C7 1.413(8) . ? C3 H3B 0.9300 . ? C7 C6 1.377(9) . ? C7 H7A 0.9300 . ? C4 H4A 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C14 C13 1.407(9) . ? C14 H14A 0.9300 . ? C13 H13A 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? O4 H1 1.02(10) . ? O4 H1B 0.78(6) . ? 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 H2 109.5 . . ? C9 N1 C14 117.5(6) . . ? C6 O3 H3A 109.5 . . ? C4 C2 C3 120.2(6) . . ? C4 C2 C1 121.6(6) . . ? C3 C2 C1 117.7(6) . . ? N2 C11 C9 119.8(6) . . ? N2 C11 C12 117.6(6) . . ? C9 C11 C12 122.5(6) . . ? N1 C9 C11 121.6(6) . . ? N1 C9 C10 114.7(6) . . ? C11 C9 C10 123.6(6) . . ? C13 N2 C11 118.5(6) . . ? C6 C5 C4 119.4(6) . . ? C6 C5 H5A 120.3 . . ? C4 C5 H5A 120.3 . . ? C7 C3 C2 119.2(6) . . ? C7 C3 H3B 120.4 . . ? C2 C3 H3B 120.4 . . ? C6 C7 C3 120.5(7) . . ? C6 C7 H7A 119.7 . . ? C3 C7 H7A 119.7 . . ? C7 C6 O3 124.0(6) . . ? C7 C6 C5 120.5(6) . . ? O3 C6 C5 115.4(6) . . ? C2 C4 C5 119.9(6) . . ? C2 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C14 C13 120.4(6) . . ? N1 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? O1 C1 O2 124.5(6) . . ? O1 C1 C2 123.4(7) . . ? O2 C1 C2 112.0(6) . . ? N2 C13 C14 122.1(7) . . ? N2 C13 H13A 119.0 . . ? C14 C13 H13A 119.0 . . ? 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 . . ? H1 O4 H1B 93(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.317 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.097 # Attachment '- 2.cif' data_lyh2 _database_code_depnum_ccdc_archive 'CCDC 877954' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N2 O3' _chemical_formula_sum 'C13 H14 N2 O3' _chemical_formula_weight 246.26 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 Orthorhombic _symmetry_space_group_name_H-M Pna21 _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 13.150(3) _cell_length_b 13.022(3) _cell_length_c 7.2410(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1239.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2125 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 24.71 _exptl_crystal_description clubbed _exptl_crystal_colour White _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku SCXmini diffractometer' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count 2 _diffrn_standards_interval_time 150 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9921 _diffrn_reflns_av_R_equivalents 0.1111 _diffrn_reflns_av_sigmaI/netI 0.0712 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2125 _reflns_number_gt 1216 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0525P)^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_number_reflns 2125 _refine_ls_number_parameters 167 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1216 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1395 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N2 N 0.2363(2) 0.0319(3) 0.7016(5) 0.0425(9) Uani 1 1 d . . . O3 O 0.65809(19) 0.0531(2) 0.6163(5) 0.0611(10) Uani 1 1 d . . . H3 H 0.5986 0.0435 0.6456 0.092 Uiso 1 1 calc R . . C4 C 0.2894(3) 0.1160(3) 0.7417(7) 0.0372(10) Uani 1 1 d . . . N1 N 0.4461(2) 0.0343(3) 0.6697(5) 0.0450(10) Uani 1 1 d . . . C7 C 0.6771(3) -0.1151(3) 0.7511(8) 0.0460(12) Uani 1 1 d . . . H7 H 0.6071 -0.1251 0.7536 0.055 Uiso 1 1 calc R . . O1 O 1.02925(19) 0.0182(2) 0.7069(6) 0.0638(10) Uani 1 1 d . . . H1 H 1.0914 0.0208 0.7149 0.096 Uiso 1 1 calc R . . C3 C 0.3950(3) 0.1175(3) 0.7232(7) 0.0433(11) Uani 1 1 d . . . C11 C 0.8458(3) -0.1780(3) 0.8105(6) 0.0486(13) Uani 1 1 d . . . H11 H 0.8886 -0.2298 0.8525 0.058 Uiso 1 1 calc R . . C9 C 0.8215(3) -0.0102(3) 0.6772(6) 0.0414(12) Uani 1 1 d . . . H9 H 0.8485 0.0503 0.6302 0.050 Uiso 1 1 calc R . . C13 C 0.9981(3) -0.0767(3) 0.7396(8) 0.0514(12) Uani 1 1 d . . . C10 C 0.8860(3) -0.0879(3) 0.7429(7) 0.0410(10) Uani 1 1 d . . . C8 C 0.7165(3) -0.0246(3) 0.6831(7) 0.0431(11) Uani 1 1 d . . . C1 C 0.2885(3) -0.0505(3) 0.6460(7) 0.0503(13) Uani 1 1 d . . . H1A H 0.2532 -0.1102 0.6165 0.060 Uiso 1 1 calc R . . O2 O 1.0559(2) -0.1469(2) 0.7619(7) 0.0895(14) Uani 1 1 d . . . C5 C 0.2292(3) 0.2067(3) 0.8057(8) 0.0574(14) Uani 1 1 d . . . H5A H 0.1583 0.1893 0.8077 0.086 Uiso 1 1 calc R . . H5B H 0.2400 0.2632 0.7228 0.086 Uiso 1 1 calc R . . H5C H 0.2508 0.2257 0.9276 0.086 Uiso 1 1 calc R . . C2 C 0.3920(3) -0.0497(3) 0.6314(7) 0.0552(14) Uani 1 1 d . . . H2 H 0.4255 -0.1090 0.5939 0.066 Uiso 1 1 calc R . . C6 C 0.4550(3) 0.2138(3) 0.7602(10) 0.0773(17) Uani 1 1 d . . . H6A H 0.5262 0.1999 0.7447 0.116 Uiso 1 1 calc R . . H6B H 0.4426 0.2365 0.8844 0.116 Uiso 1 1 calc R . . H6C H 0.4346 0.2665 0.6752 0.116 Uiso 1 1 calc R . . C12 C 0.7413(3) -0.1909(3) 0.8156(6) 0.0486(12) Uani 1 1 d . . . H12 H 0.7141 -0.2513 0.8630 0.058 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 N2 0.0272(17) 0.0479(19) 0.053(2) 0.005(2) 0.0003(19) -0.0012(17) O3 0.0262(15) 0.062(2) 0.096(3) 0.002(2) 0.0043(18) 0.0062(16) C4 0.029(2) 0.042(2) 0.041(3) 0.006(2) 0.002(2) 0.0010(19) N1 0.0256(18) 0.050(2) 0.060(3) 0.005(2) -0.002(2) 0.0031(18) C7 0.024(2) 0.057(3) 0.057(3) -0.008(3) 0.005(2) -0.006(2) O1 0.0256(14) 0.0566(17) 0.109(3) 0.010(2) -0.003(2) -0.0028(14) C3 0.032(2) 0.041(2) 0.058(3) 0.011(3) -0.002(3) -0.0011(19) C11 0.037(3) 0.051(3) 0.058(3) -0.007(2) -0.004(2) 0.004(2) C9 0.030(2) 0.040(2) 0.054(3) -0.003(3) 0.005(3) -0.0048(19) C13 0.030(3) 0.051(3) 0.073(3) -0.006(3) 0.000(3) 0.001(2) C10 0.028(2) 0.037(2) 0.057(3) -0.009(3) 0.001(2) -0.0014(18) C8 0.026(2) 0.046(2) 0.057(3) -0.012(2) 0.005(3) 0.002(2) C1 0.041(3) 0.041(3) 0.069(4) 0.002(3) -0.002(3) 0.000(2) O2 0.0320(17) 0.0582(19) 0.178(4) 0.011(3) -0.002(3) 0.0132(16) C5 0.051(3) 0.053(3) 0.068(4) -0.001(3) 0.002(3) 0.014(2) C2 0.044(3) 0.050(3) 0.071(4) 0.000(3) 0.002(3) 0.008(2) C6 0.044(3) 0.058(3) 0.130(5) 0.003(4) -0.010(4) -0.010(2) C12 0.051(3) 0.045(3) 0.049(3) -0.003(2) 0.002(3) -0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C4 1.331(4) . ? N2 C1 1.336(5) . ? O3 C8 1.359(4) . ? O3 H3 0.8200 . ? C4 C3 1.395(5) . ? C4 C5 1.495(5) . ? N1 C2 1.335(5) . ? N1 C3 1.332(4) . ? C7 C8 1.378(5) . ? C7 C12 1.380(5) . ? C7 H7 0.9300 . ? O1 C13 1.324(4) . ? O1 H1 0.8200 . ? C3 C6 1.506(5) . ? C11 C12 1.385(5) . ? C11 C10 1.377(5) . ? C11 H11 0.9300 . ? C9 C10 1.402(5) . ? C9 C8 1.393(5) . ? C9 H9 0.9300 . ? C13 O2 1.200(4) . ? C13 C10 1.482(5) . ? C1 C2 1.365(6) . ? C1 H1A 0.9300 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C2 H2 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C12 H12 0.9300 . ? 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 C4 N2 C1 117.2(3) . . ? C8 O3 H3 109.5 . . ? N2 C4 C3 120.9(4) . . ? N2 C4 C5 116.1(3) . . ? C3 C4 C5 123.0(4) . . ? C2 N1 C3 117.3(3) . . ? C8 C7 C12 120.2(4) . . ? C8 C7 H7 119.9 . . ? C12 C7 H7 119.9 . . ? C13 O1 H1 109.5 . . ? N1 C3 C4 121.2(3) . . ? N1 C3 C6 117.7(3) . . ? C4 C3 C6 121.1(4) . . ? C12 C11 C10 119.6(4) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C10 C9 C8 119.5(4) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? O2 C13 O1 122.7(3) . . ? O2 C13 C10 123.6(4) . . ? O1 C13 C10 113.7(4) . . ? C9 C10 C11 120.2(3) . . ? C9 C10 C13 121.7(4) . . ? C11 C10 C13 118.1(4) . . ? C7 C8 O3 123.4(3) . . ? C7 C8 C9 119.9(4) . . ? O3 C8 C9 116.7(4) . . ? N2 C1 C2 122.0(4) . . ? N2 C1 H1A 119.0 . . ? C2 C1 H1A 119.0 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C2 C1 121.4(4) . . ? N1 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C11 C12 C7 120.7(4) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.165 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.047