# Electronic Supplementary Material (ESI) for Molecular BioSystems # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_co397 _database_code_depnum_ccdc_archive 'CCDC 903661' #TrackingRef 'web_deposit_cif_file_0_CristinaRodriguez-Rodriguez_1348862163.co397.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 N2 O3' _chemical_formula_weight 272.30 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9251(4) _cell_length_b 8.3409(4) _cell_length_c 11.1686(6) _cell_angle_alpha 97.746(3) _cell_angle_beta 110.719(3) _cell_angle_gamma 95.600(3) _cell_volume 675.77(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6462 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 28.26 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.903 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details ? _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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12110 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3322 _reflns_number_gt 2665 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0630P)^2^+0.2032P] 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 3322 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.16144(18) 0.85429(16) 0.07540(12) 0.0214(3) Uani 1 1 d . . . H1A H 0.0324 0.8592 0.0277 0.032 Uiso 1 1 calc R . . H1B H 0.2378 0.9422 0.0594 0.032 Uiso 1 1 calc R . . H1C H 0.1855 0.8678 0.1688 0.032 Uiso 1 1 calc R . . C2 C 0.20533(16) 0.69137(15) 0.02986(11) 0.0172(3) Uani 1 1 d . . . C3 C 0.23402(16) 0.57011(15) 0.10199(11) 0.0174(3) Uani 1 1 d . . . C4 C 0.27212(16) 0.41065(16) 0.05951(12) 0.0181(3) Uani 1 1 d . . . C5 C 0.28282(17) 0.39269(16) -0.06821(12) 0.0198(3) Uani 1 1 d . . . H5 H 0.3085 0.2925 -0.1042 0.024 Uiso 1 1 calc R . . C6 C 0.25705(17) 0.51560(16) -0.13748(12) 0.0192(3) Uani 1 1 d . . . H6 H 0.2680 0.4997 -0.2201 0.023 Uiso 1 1 calc R . . C7 C 0.19202(17) 0.78829(15) -0.17285(11) 0.0178(3) Uani 1 1 d . . . C8 C 0.01724(18) 0.81770(17) -0.24180(12) 0.0216(3) Uani 1 1 d . . . H8 H -0.0870 0.7569 -0.2367 0.026 Uiso 1 1 calc R . . C9 C -0.00141(19) 0.93882(17) -0.31881(12) 0.0238(3) Uani 1 1 d . . . H9 H -0.1196 0.9600 -0.3675 0.029 Uiso 1 1 calc R . . C10 C 0.15231(19) 1.02856(16) -0.32452(12) 0.0226(3) Uani 1 1 d . . . H10 H 0.1387 1.1118 -0.3760 0.027 Uiso 1 1 calc R . . C11 C 0.32544(19) 0.99672(16) -0.25509(13) 0.0229(3) Uani 1 1 d . . . H11 H 0.4299 1.0579 -0.2597 0.028 Uiso 1 1 calc R . . C12 C 0.34682(18) 0.87539(16) -0.17862(12) 0.0209(3) Uani 1 1 d . . . H12 H 0.4650 0.8527 -0.1314 0.025 Uiso 1 1 calc R . . C13 C 0.38003(17) 0.64185(15) 0.32853(11) 0.0178(3) Uani 1 1 d . . . C14 C 0.5115(2) 0.71737(19) 0.56266(12) 0.0275(3) Uani 1 1 d . . . H14A H 0.6216 0.6915 0.5484 0.041 Uiso 1 1 calc R . . H14B H 0.4958 0.6611 0.6305 0.041 Uiso 1 1 calc R . . H14C H 0.5236 0.8359 0.5902 0.041 Uiso 1 1 calc R . . C15 C 0.1744(2) 0.6315(2) 0.45207(14) 0.0299(3) Uani 1 1 d . . . H15A H 0.0780 0.6267 0.3668 0.045 Uiso 1 1 calc R . . H15B H 0.1636 0.7198 0.5151 0.045 Uiso 1 1 calc R . . H15C H 0.1619 0.5268 0.4812 0.045 Uiso 1 1 calc R . . N1 N 0.21566(14) 0.66233(13) -0.09260(10) 0.0175(2) Uani 1 1 d . . . N2 N 0.35245(15) 0.66296(14) 0.44172(10) 0.0225(3) Uani 1 1 d . . . O1 O 0.29409(13) 0.30097(11) 0.12748(9) 0.0232(2) Uani 1 1 d . . . O2 O 0.21648(12) 0.59698(11) 0.22358(8) 0.0199(2) Uani 1 1 d . . . O3 O 0.52718(12) 0.66193(12) 0.31685(9) 0.0231(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0259(7) 0.0218(6) 0.0173(6) 0.0027(5) 0.0085(5) 0.0062(5) C2 0.0151(6) 0.0224(6) 0.0129(5) 0.0011(4) 0.0048(4) 0.0019(5) C3 0.0165(6) 0.0239(6) 0.0115(5) 0.0023(5) 0.0052(4) 0.0023(5) C4 0.0135(6) 0.0224(6) 0.0174(6) 0.0045(5) 0.0042(5) 0.0020(5) C5 0.0203(6) 0.0206(6) 0.0170(6) 0.0005(5) 0.0062(5) 0.0040(5) C6 0.0198(6) 0.0238(6) 0.0129(5) 0.0006(5) 0.0058(5) 0.0031(5) C7 0.0223(6) 0.0198(6) 0.0113(5) 0.0031(4) 0.0058(5) 0.0044(5) C8 0.0209(6) 0.0285(7) 0.0163(6) 0.0053(5) 0.0076(5) 0.0034(5) C9 0.0236(7) 0.0314(7) 0.0173(6) 0.0068(5) 0.0067(5) 0.0092(6) C10 0.0321(7) 0.0215(6) 0.0166(6) 0.0047(5) 0.0106(5) 0.0070(5) C11 0.0261(7) 0.0209(6) 0.0233(6) 0.0040(5) 0.0117(5) 0.0012(5) C12 0.0197(6) 0.0220(6) 0.0200(6) 0.0032(5) 0.0063(5) 0.0043(5) C13 0.0208(6) 0.0176(6) 0.0144(6) 0.0038(4) 0.0056(5) 0.0031(5) C14 0.0283(7) 0.0353(8) 0.0147(6) 0.0002(5) 0.0043(5) 0.0060(6) C15 0.0271(7) 0.0430(9) 0.0216(7) 0.0000(6) 0.0140(6) 0.0033(6) N1 0.0193(5) 0.0209(5) 0.0125(5) 0.0040(4) 0.0058(4) 0.0037(4) N2 0.0216(6) 0.0313(6) 0.0136(5) 0.0011(4) 0.0070(4) 0.0020(5) O1 0.0242(5) 0.0252(5) 0.0223(5) 0.0099(4) 0.0089(4) 0.0058(4) O2 0.0196(5) 0.0290(5) 0.0119(4) 0.0042(3) 0.0064(3) 0.0039(4) O3 0.0205(5) 0.0298(5) 0.0185(4) 0.0037(4) 0.0080(4) -0.0002(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5025(17) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.3633(17) . ? C2 N1 1.3891(15) . ? C3 O2 1.4040(13) . ? C3 C4 1.4474(18) . ? C4 O1 1.2523(15) . ? C4 C5 1.4474(17) . ? C5 C6 1.3543(17) . ? C5 H5 0.9500 . ? C6 N1 1.3734(16) . ? C6 H6 0.9500 . ? C7 C12 1.3898(18) . ? C7 C8 1.3908(18) . ? C7 N1 1.4545(15) . ? C8 C9 1.3984(18) . ? C8 H8 0.9500 . ? C9 C10 1.3922(19) . ? C9 H9 0.9500 . ? C10 C11 1.389(2) . ? C10 H10 0.9500 . ? C11 C12 1.3951(18) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 O3 1.2167(15) . ? C13 N2 1.3491(15) . ? C13 O2 1.3806(15) . ? C14 N2 1.4620(17) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 N2 1.4575(17) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 N1 118.31(11) . . ? C3 C2 C1 123.42(11) . . ? N1 C2 C1 118.26(11) . . ? C2 C3 O2 118.33(11) . . ? C2 C3 C4 124.68(11) . . ? O2 C3 C4 116.91(10) . . ? O1 C4 C5 124.11(11) . . ? O1 C4 C3 122.89(11) . . ? C5 C4 C3 113.00(11) . . ? C6 C5 C4 121.45(11) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 N1 122.37(11) . . ? C5 C6 H6 118.8 . . ? N1 C6 H6 118.8 . . ? C12 C7 C8 121.93(12) . . ? C12 C7 N1 118.36(11) . . ? C8 C7 N1 119.70(11) . . ? C7 C8 C9 118.45(12) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? C10 C9 C8 120.37(12) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 120.15(12) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.34(12) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C7 C12 C11 118.75(12) . . ? C7 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? O3 C13 N2 125.96(11) . . ? O3 C13 O2 122.96(11) . . ? N2 C13 O2 111.06(10) . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6 N1 C2 120.13(10) . . ? C6 N1 C7 118.72(10) . . ? C2 N1 C7 121.08(10) . . ? C13 N2 C15 124.33(11) . . ? C13 N2 C14 118.18(11) . . ? C15 N2 C14 117.47(11) . . ? C13 O2 C3 114.48(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 O2 -177.52(10) . . . . ? C1 C2 C3 O2 1.90(18) . . . . ? N1 C2 C3 C4 -1.00(18) . . . . ? C1 C2 C3 C4 178.43(12) . . . . ? C2 C3 C4 O1 -178.50(12) . . . . ? O2 C3 C4 O1 -1.93(17) . . . . ? C2 C3 C4 C5 1.82(17) . . . . ? O2 C3 C4 C5 178.38(10) . . . . ? O1 C4 C5 C6 179.73(12) . . . . ? C3 C4 C5 C6 -0.59(17) . . . . ? C4 C5 C6 N1 -1.42(19) . . . . ? C12 C7 C8 C9 -0.02(19) . . . . ? N1 C7 C8 C9 -179.60(11) . . . . ? C7 C8 C9 C10 -0.74(19) . . . . ? C8 C9 C10 C11 0.92(19) . . . . ? C9 C10 C11 C12 -0.35(19) . . . . ? C8 C7 C12 C11 0.58(19) . . . . ? N1 C7 C12 C11 -179.84(11) . . . . ? C10 C11 C12 C7 -0.39(19) . . . . ? C5 C6 N1 C2 2.36(18) . . . . ? C5 C6 N1 C7 179.39(11) . . . . ? C3 C2 N1 C6 -1.13(17) . . . . ? C1 C2 N1 C6 179.41(11) . . . . ? C3 C2 N1 C7 -178.09(11) . . . . ? C1 C2 N1 C7 2.45(17) . . . . ? C12 C7 N1 C6 -75.52(15) . . . . ? C8 C7 N1 C6 104.07(14) . . . . ? C12 C7 N1 C2 101.48(14) . . . . ? C8 C7 N1 C2 -78.93(15) . . . . ? O3 C13 N2 C15 -177.50(13) . . . . ? O2 C13 N2 C15 3.93(18) . . . . ? O3 C13 N2 C14 1.0(2) . . . . ? O2 C13 N2 C14 -177.54(11) . . . . ? O3 C13 O2 C3 2.34(17) . . . . ? N2 C13 O2 C3 -179.04(10) . . . . ? C2 C3 O2 C13 -100.14(13) . . . . ? C4 C3 O2 C13 83.07(13) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.369 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.048 data_co407 _database_code_depnum_ccdc_archive 'CCDC 903662' #TrackingRef 'web_deposit_cif_file_1_CristinaRodriguez-Rodriguez_1348862163.co407.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N2 O3' _chemical_formula_weight 282.29 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/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2499(4) _cell_length_b 17.8481(7) _cell_length_c 9.1282(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.0460(10) _cell_angle_gamma 90.00 _cell_volume 1365.30(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(2) _cell_measurement_reflns_used 9974 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 30.14 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.901 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details 'SADABS, Sheldrick (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23774 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 30.18 _reflns_number_total 4018 _reflns_number_gt 3200 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0426P)^2^+0.3632P] 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 4018 _refine_ls_number_parameters 268 _refine_ls_number_restraints 329 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0985 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.15410(12) 0.00801(5) -0.19451(12) 0.0223(2) Uani 1 1 d U A . C2 C 0.23368(12) -0.00111(6) -0.02693(12) 0.0232(2) Uani 1 1 d U . . C3 C 0.17407(13) -0.05507(6) 0.04500(13) 0.0273(2) Uani 1 1 d U A . H3 H 0.2260 -0.0625 0.1586 0.033 Uiso 1 1 calc R . . C4 C 0.04169(14) -0.09759(6) -0.04573(14) 0.0290(2) Uani 1 1 d U . . H4 H 0.0037 -0.1342 0.0051 0.035 Uiso 1 1 calc R A . C5 C -0.03562(14) -0.08670(6) -0.21144(14) 0.0293(2) Uani 1 1 d U A . H5 H -0.1275 -0.1155 -0.2743 0.035 Uiso 1 1 calc R . . C6 C 0.02104(13) -0.03382(6) -0.28552(13) 0.0263(2) Uani 1 1 d U . . H6 H -0.0320 -0.0264 -0.3991 0.032 Uiso 1 1 calc R A . C7 C 0.19250(11) 0.13107(5) -0.26521(11) 0.01968(18) Uani 1 1 d U A . C8 C 0.26793(14) 0.25154(6) -0.32509(15) 0.0321(2) Uani 1 1 d U . . H8A H 0.1779 0.2672 -0.3024 0.048 Uiso 1 1 calc R . . H8B H 0.2563 0.2731 -0.4282 0.048 Uiso 1 1 calc R . . H8C H 0.3679 0.2691 -0.2383 0.048 Uiso 1 1 calc R . . C9 C 0.39352(13) 0.13823(6) -0.37483(14) 0.0288(2) Uani 1 1 d U . . H9A H 0.4966 0.1406 -0.2801 0.043 Uiso 1 1 calc R . . H9B H 0.3997 0.1665 -0.4640 0.043 Uiso 1 1 calc R . . H9C H 0.3671 0.0859 -0.4075 0.043 Uiso 1 1 calc R . . N11 N 0.4380(9) 0.0923(6) 0.0203(9) 0.0247(16) Uani 0.531(9) 1 d PDU A 1 C12 C 0.364(2) 0.0422(12) 0.064(2) 0.0228(11) Uani 0.531(9) 1 d PDU A 1 O13 O 0.4255(11) 0.0303(5) 0.2292(10) 0.0248(10) Uani 0.531(9) 1 d PDU A 1 C14 C 0.5484(7) 0.0795(3) 0.2941(7) 0.0195(8) Uani 0.531(9) 1 d PDU A 1 C15 C 0.5574(12) 0.1193(6) 0.1686(8) 0.0215(10) Uani 0.531(9) 1 d PDU A 1 C16 C 0.6704(7) 0.1748(3) 0.1963(6) 0.0341(10) Uani 0.531(9) 1 d PDU A 1 H16 H 0.6761 0.2025 0.1101 0.041 Uiso 0.531(9) 1 calc PR A 1 C17 C 0.7749(5) 0.1882(3) 0.3563(7) 0.0383(9) Uani 0.531(9) 1 d PDU A 1 H17 H 0.8538 0.2261 0.3809 0.046 Uiso 0.531(9) 1 calc PR A 1 C18 C 0.7655(5) 0.1467(3) 0.4806(6) 0.0374(9) Uani 0.531(9) 1 d PDU A 1 H18 H 0.8390 0.1569 0.5888 0.045 Uiso 0.531(9) 1 calc PR A 1 C19 C 0.6531(5) 0.0910(3) 0.4528(5) 0.0318(8) Uani 0.531(9) 1 d PDU A 1 H19 H 0.6484 0.0623 0.5384 0.038 Uiso 0.531(9) 1 calc PR A 1 N11B N 0.4478(15) 0.0422(7) 0.2460(12) 0.0295(17) Uani 0.469(9) 1 d PDU A 2 C12B C 0.379(2) 0.0454(14) 0.089(2) 0.0228(11) Uani 0.469(9) 1 d PDU A 2 O13B O 0.4439(9) 0.0973(6) 0.0230(8) 0.0238(16) Uani 0.469(9) 1 d PDU A 2 C14B C 0.5673(14) 0.1297(7) 0.1511(9) 0.0247(15) Uani 0.469(9) 1 d PDU A 2 C15B C 0.5703(10) 0.0964(4) 0.2889(10) 0.0276(12) Uani 0.469(9) 1 d PDU A 2 C16B C 0.6807(6) 0.1174(3) 0.4438(5) 0.0331(10) Uani 0.469(9) 1 d PDU A 2 H16B H 0.6836 0.0946 0.5391 0.040 Uiso 0.469(9) 1 calc PR A 2 C17B C 0.7849(5) 0.1735(3) 0.4483(5) 0.0359(10) Uani 0.469(9) 1 d PDU A 2 H17B H 0.8627 0.1900 0.5502 0.043 Uiso 0.469(9) 1 calc PR A 2 C18B C 0.7799(6) 0.2069(3) 0.3079(6) 0.0354(10) Uani 0.469(9) 1 d PDU A 2 H18B H 0.8540 0.2455 0.3171 0.042 Uiso 0.469(9) 1 calc PR A 2 C19B C 0.6703(7) 0.1854(4) 0.1562(6) 0.0275(10) Uani 0.469(9) 1 d PDU A 2 H19B H 0.6668 0.2081 0.0606 0.033 Uiso 0.469(9) 1 calc PR A 2 N1 N 0.27051(10) 0.17046(5) -0.33453(10) 0.02247(18) Uani 1 1 d U . . O1 O 0.21319(9) 0.05558(4) -0.27784(8) 0.02344(16) Uani 1 1 d U . . O2 O 0.10844(8) 0.15624(4) -0.20493(8) 0.02327(16) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0293(5) 0.0199(4) 0.0248(5) 0.0045(4) 0.0184(4) 0.0033(4) C2 0.0259(5) 0.0236(5) 0.0240(4) 0.0044(4) 0.0145(4) 0.0075(4) C3 0.0341(5) 0.0281(5) 0.0261(5) 0.0100(4) 0.0189(4) 0.0114(4) C4 0.0363(6) 0.0245(5) 0.0361(6) 0.0099(4) 0.0247(5) 0.0050(4) C5 0.0336(6) 0.0256(5) 0.0343(6) 0.0025(4) 0.0199(5) -0.0021(4) C6 0.0329(5) 0.0253(5) 0.0250(5) 0.0026(4) 0.0163(4) -0.0003(4) C7 0.0194(4) 0.0221(4) 0.0161(4) 0.0027(3) 0.0061(3) 0.0009(3) C8 0.0370(6) 0.0230(5) 0.0430(6) 0.0045(4) 0.0234(5) -0.0005(4) C9 0.0286(5) 0.0325(6) 0.0326(5) 0.0063(4) 0.0201(4) 0.0039(4) N11 0.016(2) 0.028(2) 0.019(2) 0.0002(17) -0.0039(18) 0.0019(16) C12 0.022(2) 0.0271(15) 0.019(4) -0.001(3) 0.008(2) 0.0083(12) O13 0.0187(15) 0.032(2) 0.0192(16) -0.0014(13) 0.0042(12) 0.0020(11) C14 0.0156(17) 0.025(2) 0.0171(11) -0.0009(13) 0.0058(10) 0.0041(13) C15 0.0148(13) 0.024(2) 0.024(2) -0.0017(16) 0.0067(16) 0.0026(12) C16 0.0272(15) 0.0330(17) 0.043(2) 0.0022(17) 0.0157(18) 0.0023(12) C17 0.0222(12) 0.041(2) 0.045(2) -0.0104(17) 0.0075(16) -0.0025(12) C18 0.0224(14) 0.047(2) 0.0338(16) -0.0153(15) 0.0035(12) 0.0049(15) C19 0.0228(14) 0.043(2) 0.0255(13) -0.0067(13) 0.0059(9) 0.0074(13) N11B 0.032(4) 0.038(4) 0.016(2) 0.005(2) 0.008(2) 0.014(3) C12B 0.022(2) 0.0271(15) 0.019(4) -0.001(3) 0.008(2) 0.0083(12) O13B 0.025(3) 0.027(2) 0.025(3) -0.0016(17) 0.017(2) 0.0027(17) C14B 0.022(3) 0.032(4) 0.0176(15) 0.0013(15) 0.0061(14) 0.012(2) C15B 0.020(2) 0.031(3) 0.0314(18) 0.0010(17) 0.0100(14) 0.0065(17) C16B 0.030(2) 0.043(2) 0.0208(12) -0.0014(16) 0.0058(13) 0.0096(18) C17B 0.0242(15) 0.046(2) 0.0297(18) -0.0102(17) 0.0034(13) 0.0078(16) C18B 0.0232(14) 0.042(2) 0.0349(19) -0.0063(15) 0.0063(13) 0.0068(14) C19B 0.0183(13) 0.034(2) 0.0261(17) -0.0008(15) 0.0058(13) 0.0029(12) N1 0.0233(4) 0.0219(4) 0.0253(4) 0.0049(3) 0.0133(3) 0.0016(3) O1 0.0325(4) 0.0207(3) 0.0247(3) 0.0027(3) 0.0194(3) 0.0000(3) O2 0.0235(3) 0.0262(4) 0.0229(3) 0.0032(3) 0.0126(3) 0.0035(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.3772(15) . ? C1 O1 1.3965(11) . ? C1 C2 1.3982(14) . ? C2 C12 1.377(7) . ? C2 C3 1.4033(14) . ? C2 C12B 1.549(8) . ? C3 C4 1.3793(17) . ? C3 H3 0.9500 . ? C4 C5 1.3862(16) . ? C4 H4 0.9500 . ? C5 C6 1.3866(14) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O2 1.2130(12) . ? C7 N1 1.3424(12) . ? C7 O1 1.3725(12) . ? C8 N1 1.4505(14) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 N1 1.4544(13) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N11 C12 1.286(19) . ? N11 C15 1.420(9) . ? C12 O13 1.386(19) . ? O13 C14 1.357(7) . ? C14 C19 1.375(7) . ? C14 C15 1.380(5) . ? C15 C16 1.384(8) . ? C16 C17 1.389(5) . ? C16 H16 0.9500 . ? C17 C18 1.389(5) . ? C17 H17 0.9500 . ? C18 C19 1.382(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? N11B C12B 1.30(2) . ? N11B C15B 1.414(10) . ? C12B O13B 1.38(2) . ? O13B C14B 1.369(9) . ? C14B C19B 1.365(9) . ? C14B C15B 1.380(5) . ? C15B C16B 1.400(8) . ? C16B C17B 1.379(5) . ? C16B H16B 0.9500 . ? C17B C18B 1.396(5) . ? C17B H17B 0.9500 . ? C18B C19B 1.380(6) . ? C18B H18B 0.9500 . ? C19B H19B 0.9500 . ? 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 C6 C1 O1 117.19(9) . . ? C6 C1 C2 121.27(9) . . ? O1 C1 C2 121.36(9) . . ? C12 C2 C1 121.0(9) . . ? C12 C2 C3 121.5(9) . . ? C1 C2 C3 117.55(10) . . ? C12 C2 C12B 5.1(18) . . ? C1 C2 C12B 125.9(9) . . ? C3 C2 C12B 116.5(9) . . ? C4 C3 C2 121.43(10) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 119.65(10) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 120.05(11) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 120.04(10) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? O2 C7 N1 126.55(9) . . ? O2 C7 O1 122.72(9) . . ? N1 C7 O1 110.66(8) . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C12 N11 C15 104.0(8) . . ? N11 C12 C2 130.6(15) . . ? N11 C12 O13 114.6(5) . . ? C2 C12 O13 114.8(14) . . ? C14 O13 C12 104.9(7) . . ? O13 C14 C19 130.0(5) . . ? O13 C14 C15 107.7(7) . . ? C19 C14 C15 122.3(5) . . ? C14 C15 C16 121.5(6) . . ? C14 C15 N11 108.7(7) . . ? C16 C15 N11 129.7(6) . . ? C15 C16 C17 116.8(4) . . ? C15 C16 H16 121.6 . . ? C17 C16 H16 121.6 . . ? C16 C17 C18 120.8(4) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 122.4(3) . . ? C19 C18 H18 118.8 . . ? C17 C18 H18 118.8 . . ? C14 C19 C18 116.1(4) . . ? C14 C19 H19 121.9 . . ? C18 C19 H19 121.9 . . ? C12B N11B C15B 103.8(10) . . ? N11B C12B O13B 114.1(6) . . ? N11B C12B C2 127.4(16) . . ? O13B C12B C2 118.5(14) . . ? C14B O13B C12B 105.9(8) . . ? C19B C14B O13B 130.8(7) . . ? C19B C14B C15B 122.6(7) . . ? O13B C14B C15B 106.6(8) . . ? C14B C15B C16B 122.0(6) . . ? C14B C15B N11B 109.7(8) . . ? C16B C15B N11B 128.3(7) . . ? C17B C16B C15B 115.2(4) . . ? C17B C16B H16B 122.4 . . ? C15B C16B H16B 122.4 . . ? C16B C17B C18B 122.1(4) . . ? C16B C17B H17B 118.9 . . ? C18B C17B H17B 118.9 . . ? C19B C18B C17B 121.9(4) . . ? C19B C18B H18B 119.1 . . ? C17B C18B H18B 119.1 . . ? C14B C19B C18B 116.2(5) . . ? C14B C19B H19B 121.9 . . ? C18B C19B H19B 121.9 . . ? C7 N1 C8 117.97(9) . . ? C7 N1 C9 123.11(9) . . ? C8 N1 C9 116.35(8) . . ? C7 O1 C1 116.77(7) . . ? 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 C12 -178.4(13) . . . . ? O1 C1 C2 C12 6.6(13) . . . . ? C6 C1 C2 C3 0.70(15) . . . . ? O1 C1 C2 C3 -174.29(9) . . . . ? C6 C1 C2 C12B -176.6(14) . . . . ? O1 C1 C2 C12B 8.4(14) . . . . ? C12 C2 C3 C4 179.0(13) . . . . ? C1 C2 C3 C4 -0.12(15) . . . . ? C12B C2 C3 C4 177.5(13) . . . . ? C2 C3 C4 C5 -0.55(16) . . . . ? C3 C4 C5 C6 0.64(16) . . . . ? O1 C1 C6 C5 174.58(9) . . . . ? C2 C1 C6 C5 -0.62(16) . . . . ? C4 C5 C6 C1 -0.07(16) . . . . ? C15 N11 C12 C2 177(2) . . . . ? C15 N11 C12 O13 -2(2) . . . . ? C1 C2 C12 N11 -3(3) . . . . ? C3 C2 C12 N11 178(2) . . . . ? C12B C2 C12 N11 -166(28) . . . . ? C1 C2 C12 O13 176.3(12) . . . . ? C3 C2 C12 O13 -3(3) . . . . ? C12B C2 C12 O13 13(24) . . . . ? N11 C12 O13 C14 1(2) . . . . ? C2 C12 O13 C14 -178.3(15) . . . . ? C12 O13 C14 C19 -178.6(13) . . . . ? C12 O13 C14 C15 0.3(16) . . . . ? O13 C14 C15 C16 179.1(11) . . . . ? C19 C14 C15 C16 -1.9(16) . . . . ? O13 C14 C15 N11 -1.5(13) . . . . ? C19 C14 C15 N11 177.5(8) . . . . ? C12 N11 C15 C14 2.1(17) . . . . ? C12 N11 C15 C16 -178.6(17) . . . . ? C14 C15 C16 C17 0.5(15) . . . . ? N11 C15 C16 C17 -178.8(11) . . . . ? C15 C16 C17 C18 0.5(10) . . . . ? C16 C17 C18 C19 -0.3(7) . . . . ? O13 C14 C19 C18 -179.2(8) . . . . ? C15 C14 C19 C18 2.0(10) . . . . ? C17 C18 C19 C14 -0.9(7) . . . . ? C15B N11B C12B O13B 0(3) . . . . ? C15B N11B C12B C2 -179(2) . . . . ? C12 C2 C12B N11B -168(28) . . . . ? C1 C2 C12B N11B 174(2) . . . . ? C3 C2 C12B N11B -3(3) . . . . ? C12 C2 C12B O13B 13(23) . . . . ? C1 C2 C12B O13B -5(3) . . . . ? C3 C2 C12B O13B 178.0(16) . . . . ? N11B C12B O13B C14B 0(3) . . . . ? C2 C12B O13B C14B 179.7(18) . . . . ? C12B O13B C14B C19B -178.5(19) . . . . ? C12B O13B C14B C15B -0.5(19) . . . . ? C19B C14B C15B C16B -0.5(19) . . . . ? O13B C14B C15B C16B -178.7(9) . . . . ? C19B C14B C15B N11B 178.7(13) . . . . ? O13B C14B C15B N11B 0.5(15) . . . . ? C12B N11B C15B C14B 0(2) . . . . ? C12B N11B C15B C16B 178.9(17) . . . . ? C14B C15B C16B C17B 0.2(12) . . . . ? N11B C15B C16B C17B -178.8(10) . . . . ? C15B C16B C17B C18B 0.1(8) . . . . ? C16B C17B C18B C19B -0.2(8) . . . . ? O13B C14B C19B C18B 178.1(12) . . . . ? C15B C14B C19B C18B 0.4(18) . . . . ? C17B C18B C19B C14B -0.1(12) . . . . ? O2 C7 N1 C8 6.09(15) . . . . ? O1 C7 N1 C8 -176.99(9) . . . . ? O2 C7 N1 C9 167.23(10) . . . . ? O1 C7 N1 C9 -15.85(13) . . . . ? O2 C7 O1 C1 -10.20(13) . . . . ? N1 C7 O1 C1 172.75(8) . . . . ? C6 C1 O1 C7 108.82(10) . . . . ? C2 C1 O1 C7 -75.99(12) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.18 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.313 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.039 data_co410 _database_code_depnum_ccdc_archive 'CCDC 903663' #TrackingRef 'web_deposit_cif_file_2_CristinaRodriguez-Rodriguez_1348862163.co410.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N2 O2 S' _chemical_formula_weight 298.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' S S 0.1246 0.1234 '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' 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 9.7184(4) _cell_length_b 13.6885(6) _cell_length_c 10.8658(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.839(3) _cell_angle_gamma 90.00 _cell_volume 1383.50(10) _cell_formula_units_Z 4 _cell_measurement_temperature 90.0(1) _cell_measurement_reflns_used 9957 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 30.1 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.813 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details 'SADABS, Sheldrick (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(1) _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 APEX DUO' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21989 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 30.10 _reflns_number_total 4066 _reflns_number_gt 3256 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0344P)^2^+1.1247P] 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 4066 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.69948(14) 0.94302(9) 0.98859(13) 0.0141(2) Uani 1 1 d . . . C2 C 0.60684(14) 0.89799(9) 1.04821(13) 0.0140(2) Uani 1 1 d . . . C3 C 0.62031(16) 0.92370(10) 1.17608(14) 0.0170(3) Uani 1 1 d . . . H3 H 0.5588 0.8942 1.2193 0.020 Uiso 1 1 calc R . . C4 C 0.72162(16) 0.99129(10) 1.24039(14) 0.0190(3) Uani 1 1 d . . . H4 H 0.7293 1.0079 1.3270 0.023 Uiso 1 1 calc R . . C5 C 0.81195(15) 1.03478(10) 1.17823(14) 0.0185(3) Uani 1 1 d . . . H5 H 0.8812 1.0814 1.2224 0.022 Uiso 1 1 calc R . . C6 C 0.80158(15) 1.01060(10) 1.05236(14) 0.0166(3) Uani 1 1 d . . . H6 H 0.8638 1.0400 1.0099 0.020 Uiso 1 1 calc R . . C7 C 0.78712(15) 0.87895(10) 0.82290(14) 0.0172(3) Uani 1 1 d . . . C8 C 0.62686(17) 0.91623(12) 0.60572(14) 0.0230(3) Uani 1 1 d . . . H8A H 0.5522 0.9264 0.6487 0.035 Uiso 1 1 calc R . . H8B H 0.5891 0.8746 0.5300 0.035 Uiso 1 1 calc R . . H8C H 0.6559 0.9794 0.5789 0.035 Uiso 1 1 calc R . . C9 C 0.85139(19) 0.82122(13) 0.63771(17) 0.0284(4) Uani 1 1 d . . . H9A H 0.8990 0.8703 0.5986 0.043 Uiso 1 1 calc R . . H9B H 0.7994 0.7750 0.5716 0.043 Uiso 1 1 calc R . . H9C H 0.9237 0.7860 0.7048 0.043 Uiso 1 1 calc R . . C12 C 0.49465(14) 0.82741(9) 0.98458(13) 0.0129(2) Uani 1 1 d . . . C14 C 0.32970(14) 0.71293(9) 0.84252(13) 0.0131(2) Uani 1 1 d . . . C15 C 0.30733(14) 0.72968(9) 0.96266(13) 0.0135(2) Uani 1 1 d . . . C16 C 0.19233(16) 0.68422(10) 0.99301(14) 0.0178(3) Uani 1 1 d . . . H16 H 0.1765 0.6944 1.0743 0.021 Uiso 1 1 calc R . . C17 C 0.10243(16) 0.62438(10) 0.90266(14) 0.0187(3) Uani 1 1 d . . . H17 H 0.0231 0.5940 0.9216 0.022 Uiso 1 1 calc R . . C18 C 0.12630(16) 0.60774(10) 0.78339(14) 0.0178(3) Uani 1 1 d . . . H18 H 0.0629 0.5661 0.7228 0.021 Uiso 1 1 calc R . . C19 C 0.24037(15) 0.65073(10) 0.75232(13) 0.0160(3) Uani 1 1 d . . . H19 H 0.2575 0.6383 0.6720 0.019 Uiso 1 1 calc R . . N1 N 0.75076(14) 0.86911(9) 0.69418(12) 0.0203(3) Uani 1 1 d . . . N11 N 0.40340(13) 0.79402(8) 1.04163(11) 0.0140(2) Uani 1 1 d . . . O1 O 0.67812(10) 0.92568(7) 0.85821(9) 0.0156(2) Uani 1 1 d . . . O2 O 0.89574(12) 0.85061(8) 0.90006(11) 0.0237(2) Uani 1 1 d . . . S13 S 0.47378(4) 0.78209(2) 0.82945(3) 0.01402(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0149(6) 0.0121(5) 0.0141(6) 0.0015(5) 0.0025(5) 0.0028(5) C2 0.0150(6) 0.0104(5) 0.0155(6) 0.0007(5) 0.0028(5) 0.0019(5) C3 0.0190(7) 0.0151(6) 0.0168(6) -0.0010(5) 0.0048(5) 0.0004(5) C4 0.0206(7) 0.0166(6) 0.0175(7) -0.0036(5) 0.0017(5) 0.0018(5) C5 0.0161(6) 0.0133(6) 0.0225(7) -0.0025(5) -0.0002(5) 0.0006(5) C6 0.0138(6) 0.0122(6) 0.0218(7) 0.0025(5) 0.0021(5) 0.0003(5) C7 0.0177(6) 0.0130(6) 0.0220(7) -0.0016(5) 0.0074(5) -0.0030(5) C8 0.0260(8) 0.0251(7) 0.0166(7) -0.0010(6) 0.0040(6) -0.0065(6) C9 0.0278(8) 0.0307(8) 0.0307(9) -0.0134(7) 0.0148(7) -0.0073(7) C12 0.0152(6) 0.0096(5) 0.0130(6) 0.0000(4) 0.0029(5) 0.0011(4) C14 0.0147(6) 0.0104(5) 0.0141(6) 0.0017(5) 0.0043(5) 0.0004(4) C15 0.0146(6) 0.0114(5) 0.0139(6) 0.0002(5) 0.0031(5) 0.0012(5) C16 0.0196(7) 0.0175(6) 0.0177(7) -0.0008(5) 0.0079(5) -0.0012(5) C17 0.0181(7) 0.0169(6) 0.0227(7) 0.0003(5) 0.0083(5) -0.0028(5) C18 0.0184(7) 0.0141(6) 0.0200(7) -0.0013(5) 0.0040(5) -0.0027(5) C19 0.0196(7) 0.0130(6) 0.0154(6) -0.0006(5) 0.0051(5) -0.0009(5) N1 0.0236(6) 0.0193(6) 0.0197(6) -0.0025(5) 0.0091(5) -0.0028(5) N11 0.0149(5) 0.0131(5) 0.0142(5) -0.0006(4) 0.0043(4) -0.0002(4) O1 0.0153(5) 0.0170(4) 0.0147(5) 0.0011(4) 0.0046(4) 0.0006(4) O2 0.0200(5) 0.0240(5) 0.0264(6) -0.0016(4) 0.0055(4) 0.0038(4) S13 0.01709(16) 0.01217(14) 0.01355(15) -0.00119(11) 0.00561(12) -0.00253(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.3864(19) . ? C1 O1 1.3915(16) . ? C1 C2 1.3957(19) . ? C2 C3 1.4022(19) . ? C2 C12 1.4709(18) . ? C3 C4 1.384(2) . ? C3 H3 0.9500 . ? C4 C5 1.387(2) . ? C4 H4 0.9500 . ? C5 C6 1.382(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O2 1.2062(18) . ? C7 N1 1.3465(19) . ? C7 O1 1.3834(17) . ? C8 N1 1.456(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 N1 1.453(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C12 N11 1.3032(17) . ? C12 S13 1.7519(13) . ? C14 C19 1.3952(19) . ? C14 C15 1.4030(18) . ? C14 S13 1.7298(13) . ? C15 N11 1.3855(17) . ? C15 C16 1.3995(19) . ? C16 C17 1.379(2) . ? C16 H16 0.9500 . ? C17 C18 1.400(2) . ? C17 H17 0.9500 . ? C18 C19 1.3806(19) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? 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 C6 C1 O1 119.79(12) . . ? C6 C1 C2 121.82(13) . . ? O1 C1 C2 118.11(12) . . ? C1 C2 C3 117.48(12) . . ? C1 C2 C12 124.19(12) . . ? C3 C2 C12 118.32(12) . . ? C4 C3 C2 121.11(13) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.94(14) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.26(13) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 119.39(13) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? O2 C7 N1 127.11(14) . . ? O2 C7 O1 122.83(13) . . ? N1 C7 O1 110.04(12) . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N11 C12 C2 121.38(12) . . ? N11 C12 S13 115.37(10) . . ? C2 C12 S13 123.25(10) . . ? C19 C14 C15 121.39(12) . . ? C19 C14 S13 129.06(11) . . ? C15 C14 S13 109.53(10) . . ? N11 C15 C16 125.28(12) . . ? N11 C15 C14 114.95(12) . . ? C16 C15 C14 119.75(12) . . ? C17 C16 C15 118.75(13) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 121.00(13) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C19 C18 C17 121.14(13) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C14 117.95(13) . . ? C18 C19 H19 121.0 . . ? C14 C19 H19 121.0 . . ? C7 N1 C9 118.53(14) . . ? C7 N1 C8 124.02(13) . . ? C9 N1 C8 116.77(13) . . ? C12 N11 C15 110.96(11) . . ? C7 O1 C1 117.44(11) . . ? C14 S13 C12 89.18(6) . . ? 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(2) . . . . ? O1 C1 C2 C3 -173.75(12) . . . . ? C6 C1 C2 C12 178.68(12) . . . . ? O1 C1 C2 C12 4.82(19) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C12 C2 C3 C4 -178.58(13) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? C4 C5 C6 C1 0.4(2) . . . . ? O1 C1 C6 C5 173.39(12) . . . . ? C2 C1 C6 C5 -0.4(2) . . . . ? C1 C2 C12 N11 -174.10(13) . . . . ? C3 C2 C12 N11 4.47(19) . . . . ? C1 C2 C12 S13 6.13(19) . . . . ? C3 C2 C12 S13 -175.31(10) . . . . ? C19 C14 C15 N11 -179.26(12) . . . . ? S13 C14 C15 N11 -1.02(15) . . . . ? C19 C14 C15 C16 -0.7(2) . . . . ? S13 C14 C15 C16 177.52(11) . . . . ? N11 C15 C16 C17 177.75(13) . . . . ? C14 C15 C16 C17 -0.6(2) . . . . ? C15 C16 C17 C18 1.0(2) . . . . ? C16 C17 C18 C19 -0.1(2) . . . . ? C17 C18 C19 C14 -1.3(2) . . . . ? C15 C14 C19 C18 1.6(2) . . . . ? S13 C14 C19 C18 -176.22(11) . . . . ? O2 C7 N1 C9 -1.3(2) . . . . ? O1 C7 N1 C9 -179.76(12) . . . . ? O2 C7 N1 C8 -171.55(14) . . . . ? O1 C7 N1 C8 9.98(19) . . . . ? C2 C12 N11 C15 179.31(11) . . . . ? S13 C12 N11 C15 -0.90(15) . . . . ? C16 C15 N11 C12 -177.21(13) . . . . ? C14 C15 N11 C12 1.24(16) . . . . ? O2 C7 O1 C1 2.38(19) . . . . ? N1 C7 O1 C1 -179.07(11) . . . . ? C6 C1 O1 C7 68.96(16) . . . . ? C2 C1 O1 C7 -117.06(13) . . . . ? C19 C14 S13 C12 178.48(13) . . . . ? C15 C14 S13 C12 0.42(10) . . . . ? N11 C12 S13 C14 0.28(11) . . . . ? C2 C12 S13 C14 -179.93(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.392 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.062 data_co412 _database_code_depnum_ccdc_archive 'CCDC 903664' #TrackingRef 'web_deposit_cif_file_3_CristinaRodriguez-Rodriguez_1348862163.co412.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 N O3' _chemical_formula_weight 233.26 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5969(11) _cell_length_b 9.6007(14) _cell_length_c 9.9994(15) _cell_angle_alpha 100.928(4) _cell_angle_beta 111.838(3) _cell_angle_gamma 107.261(3) _cell_volume 608.35(15) _cell_formula_units_Z 2 _cell_measurement_temperature 90.0(1) _cell_measurement_reflns_used 5812 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.73 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.788 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details 'SADABS, Sheldrick (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90.0(1) _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 APEX DUO' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13793 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 28.78 _reflns_number_total 3135 _reflns_number_gt 2250 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0749P)^2^+0.2121P] 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 3135 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1473 _refine_ls_wR_factor_gt 0.1314 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 C1 C 0.1244(2) 0.0503(2) 0.79775(19) 0.0275(4) Uani 1 1 d . . . H1A H 0.0598 0.1248 0.7970 0.041 Uiso 1 1 calc R . . H1B H 0.1220 0.0063 0.8781 0.041 Uiso 1 1 calc R . . H1C H 0.0476 -0.0329 0.6981 0.041 Uiso 1 1 calc R . . C2 C 0.3444(2) 0.13108(17) 0.82830(16) 0.0173(3) Uani 1 1 d . . . C3 C 0.4081(2) 0.10473(17) 0.71827(16) 0.0176(3) Uani 1 1 d . . . C4 C 0.6206(2) 0.17497(17) 0.74907(17) 0.0180(3) Uani 1 1 d . . . C5 C 0.7610(2) 0.27107(19) 0.90210(18) 0.0231(3) Uani 1 1 d . . . H5 H 0.9046 0.3180 0.9306 0.028 Uiso 1 1 calc R . . C6 C 0.6944(2) 0.29752(18) 1.00917(17) 0.0212(3) Uani 1 1 d . . . H6 H 0.7920 0.3643 1.1107 0.025 Uiso 1 1 calc R . . C7 C 0.4333(2) 0.26793(17) 1.09450(17) 0.0182(3) Uani 1 1 d . . . C8 C 0.4934(3) 0.2118(2) 1.21433(19) 0.0280(4) Uani 1 1 d . . . H8 H 0.5682 0.1480 1.2158 0.034 Uiso 1 1 calc R . . C9 C 0.4431(3) 0.2501(2) 1.3322(2) 0.0340(4) Uani 1 1 d . . . H9 H 0.4832 0.2125 1.4151 0.041 Uiso 1 1 calc R . . C10 C 0.3346(3) 0.3429(2) 1.32867(19) 0.0304(4) Uani 1 1 d . . . H10 H 0.2983 0.3675 1.4087 0.036 Uiso 1 1 calc R . . C11 C 0.2781(2) 0.4007(2) 1.20967(19) 0.0270(4) Uani 1 1 d . . . H11 H 0.2056 0.4662 1.2093 0.032 Uiso 1 1 calc R . . C12 C 0.3274(2) 0.36284(19) 1.09057(17) 0.0221(3) Uani 1 1 d . . . H12 H 0.2890 0.4016 1.0083 0.027 Uiso 1 1 calc R . . C13 C 1.1034(3) 0.3599(2) 0.5984(2) 0.0290(4) Uani 1 1 d . . . H13A H 1.2374 0.4443 0.6314 0.043 Uiso 1 1 calc R . . H13B H 1.0018 0.3573 0.5013 0.043 Uiso 1 1 calc R . . H13C H 1.1185 0.2610 0.5844 0.043 Uiso 1 1 calc R . . N1 N 0.49078(18) 0.23030(14) 0.97405(14) 0.0171(3) Uani 1 1 d . . . O1 O 0.67255(16) 0.14855(13) 0.64304(12) 0.0235(3) Uani 1 1 d . . . O2 O 0.26579(16) 0.00795(14) 0.57502(12) 0.0251(3) Uani 1 1 d . . . O3 O 1.0347(2) 0.38459(16) 0.71149(15) 0.0363(3) Uani 1 1 d . . . H2O H 0.331(3) -0.016(3) 0.516(3) 0.037(6) Uiso 1 1 d . . . H3O H 0.917(4) 0.298(3) 0.685(3) 0.054(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 C1 0.0169(7) 0.0287(9) 0.0201(8) -0.0073(7) 0.0071(6) -0.0011(6) C2 0.0145(6) 0.0138(7) 0.0143(7) -0.0024(6) 0.0029(5) 0.0029(5) C3 0.0139(6) 0.0144(7) 0.0129(7) -0.0040(6) 0.0011(5) 0.0026(5) C4 0.0155(6) 0.0159(7) 0.0147(7) -0.0017(6) 0.0045(5) 0.0037(6) C5 0.0134(6) 0.0255(8) 0.0169(7) -0.0045(6) 0.0038(6) 0.0017(6) C6 0.0146(6) 0.0219(8) 0.0138(7) -0.0038(6) 0.0013(5) 0.0029(6) C7 0.0165(6) 0.0157(7) 0.0128(7) -0.0030(6) 0.0051(5) 0.0009(5) C8 0.0366(9) 0.0224(8) 0.0225(8) 0.0059(7) 0.0129(7) 0.0105(7) C9 0.0444(10) 0.0300(9) 0.0210(8) 0.0080(8) 0.0155(8) 0.0063(8) C10 0.0254(8) 0.0304(9) 0.0187(8) -0.0060(7) 0.0123(7) -0.0041(7) C11 0.0185(7) 0.0306(9) 0.0202(8) -0.0059(7) 0.0077(6) 0.0054(7) C12 0.0181(7) 0.0252(8) 0.0155(7) 0.0002(6) 0.0052(6) 0.0062(6) C13 0.0247(8) 0.0263(9) 0.0248(9) -0.0018(7) 0.0122(7) 0.0013(7) N1 0.0151(6) 0.0162(6) 0.0123(6) -0.0018(5) 0.0038(5) 0.0037(5) O1 0.0178(5) 0.0234(6) 0.0167(5) -0.0056(5) 0.0072(4) 0.0009(4) O2 0.0142(5) 0.0283(6) 0.0135(5) -0.0100(5) 0.0022(4) -0.0002(4) O3 0.0278(6) 0.0310(7) 0.0278(7) -0.0124(6) 0.0163(5) -0.0075(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.500(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.368(2) . ? C2 N1 1.3810(18) . ? C3 O2 1.3532(17) . ? C3 C4 1.4356(19) . ? C4 O1 1.2699(17) . ? C4 C5 1.413(2) . ? C5 C6 1.357(2) . ? C5 H5 0.9500 . ? C6 N1 1.3604(18) . ? C6 H6 0.9500 . ? C7 C12 1.380(2) . ? C7 C8 1.385(2) . ? C7 N1 1.4464(18) . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 C10 1.378(3) . ? C9 H9 0.9500 . ? C10 C11 1.385(3) . ? C10 H10 0.9500 . ? C11 C12 1.393(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 O3 1.4211(19) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O2 H2O 0.94(2) . ? O3 H3O 0.92(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 N1 118.40(13) . . ? C3 C2 C1 122.29(13) . . ? N1 C2 C1 119.24(13) . . ? O2 C3 C2 118.83(13) . . ? O2 C3 C4 118.61(13) . . ? C2 C3 C4 122.55(13) . . ? O1 C4 C5 124.19(13) . . ? O1 C4 C3 120.44(13) . . ? C5 C4 C3 115.37(13) . . ? C6 C5 C4 121.20(13) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 N1 121.33(14) . . ? C5 C6 H6 119.3 . . ? N1 C6 H6 119.3 . . ? C12 C7 C8 121.67(14) . . ? C12 C7 N1 119.61(13) . . ? C8 C7 N1 118.68(13) . . ? C7 C8 C9 119.12(16) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 119.87(16) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.65(15) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C12 120.00(16) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C7 C12 C11 118.67(15) . . ? C7 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? O3 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C6 N1 C2 121.11(12) . . ? C6 N1 C7 117.52(12) . . ? C2 N1 C7 121.36(12) . . ? C3 O2 H2O 110.6(14) . . ? C13 O3 H3O 108.4(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 O2 -179.85(13) . . . . ? C1 C2 C3 O2 3.2(2) . . . . ? N1 C2 C3 C4 0.6(2) . . . . ? C1 C2 C3 C4 -176.40(15) . . . . ? O2 C3 C4 O1 1.2(2) . . . . ? C2 C3 C4 O1 -179.24(14) . . . . ? O2 C3 C4 C5 -178.29(14) . . . . ? C2 C3 C4 C5 1.3(2) . . . . ? O1 C4 C5 C6 178.35(15) . . . . ? C3 C4 C5 C6 -2.2(2) . . . . ? C4 C5 C6 N1 1.3(3) . . . . ? C12 C7 C8 C9 1.0(2) . . . . ? N1 C7 C8 C9 178.57(15) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C9 C10 C11 C12 1.2(2) . . . . ? C8 C7 C12 C11 -0.9(2) . . . . ? N1 C7 C12 C11 -178.43(13) . . . . ? C10 C11 C12 C7 -0.2(2) . . . . ? C5 C6 N1 C2 0.8(2) . . . . ? C5 C6 N1 C7 -178.61(14) . . . . ? C3 C2 N1 C6 -1.7(2) . . . . ? C1 C2 N1 C6 175.42(14) . . . . ? C3 C2 N1 C7 177.68(13) . . . . ? C1 C2 N1 C7 -5.2(2) . . . . ? C12 C7 N1 C6 107.45(16) . . . . ? C8 C7 N1 C6 -70.15(19) . . . . ? C12 C7 N1 C2 -71.92(19) . . . . ? C8 C7 N1 C2 110.48(16) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.78 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.379 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.059