# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email vr.chepuri@ncl.res.in _publ_contact_author_name 'Cehpuri Ramana' loop_ _publ_author_name 'Cehpuri Ramana' 'Pitambar Patel' data_ptmb10 _database_code_depnum_ccdc_archive 'CCDC 795522' #TrackingRef 'ptmb10.cif' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 14.476(8) _cell_length_b 5.258(3) _cell_length_c 17.353(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.049(10) _cell_angle_gamma 90.00 _cell_volume 1315.7 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z O1 O 0.0980(3) 0.5041(10) 0.8324(3) O2 O 0.1997(3) 0.1460(9) 0.8553(3) O3 O 0.1897(4) 0.6379(12) 0.9975(3) O4 O 0.6228(4) 0.4468(13) 0.7953(3) O5 O 0.6439(4) 0.7848(12) 0.8775(3) C1 C 0.1476(4) 0.3478(13) 0.8898(4) C2 C 0.0718(5) 0.2070(15) 0.9339(4) H2A H 0.0905 0.0339 0.9468 H2B H 0.0602 0.2965 0.9810 C3 C -0.0134(5) 0.2113(15) 0.8759(5) H3A H -0.0143 0.0649 0.8418 H3B H -0.0699 0.2133 0.9020 C4 C -0.0024(5) 0.4551(16) 0.8315(5) H4A H -0.0299 0.4376 0.7787 H4B H -0.0328 0.5944 0.8558 C5 C 0.2160(5) 0.5232(14) 0.9402(4) C6 C 0.3134(4) 0.5469(13) 0.9159(4) C7 C 0.3371(4) 0.4017(12) 0.8501(3) C8 C 0.4298(5) 0.4246(13) 0.8271(4) H8 H 0.4471 0.3314 0.7851 C9 C 0.4940(5) 0.5853(14) 0.8671(4) C10 C 0.4694(5) 0.7346(18) 0.9304(5) H10 H 0.5124 0.8444 0.9557 C11 C 0.3788(5) 0.7144(16) 0.9545(5) H11 H 0.3620 0.8115 0.9958 C12 C 0.5939(5) 0.5943(16) 0.8423(4) C13 C 0.7405(6) 0.820(2) 0.8555(6) H13A H 0.7767 0.6718 0.8703 H13B H 0.7677 0.9663 0.8815 H13C H 0.7393 0.8435 0.8005 N1 N 0.2682(4) 0.2553(11) 0.8070(3) H1 H 0.2667 0.2328 0.7578 #END data_ptmb15 _database_code_depnum_ccdc_archive 'CCDC 836106' #TrackingRef 'PATEL-OBC-2BB.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N O2' _chemical_formula_sum 'C13 H15 N O2' _chemical_formula_weight 217.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.863(4) _cell_length_b 9.081(3) _cell_length_c 10.470(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.446(6) _cell_angle_gamma 90.00 _cell_volume 1126.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2820 _cell_measurement_theta_min 2.825 _cell_measurement_theta_max 26.99 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9613 _exptl_absorpt_correction_T_max 0.9957 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7790 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1983 _reflns_number_gt 1729 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Ortep32' _computing_publication_material SHELXTL _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^)+(0.0502P)^2^+0.3234P] 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 1983 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1194 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.18010(10) 0.18065(14) 0.26219(11) 0.0498(4) Uani 1 1 d . . . O2 O 0.27518(12) 0.45812(15) 0.32114(12) 0.0587(4) Uani 1 1 d . . . N1 N 0.29940(12) 0.18544(16) 0.08444(15) 0.0434(4) Uani 1 1 d . . . C2 C 0.22446(14) 0.26887(19) 0.16407(15) 0.0396(4) Uani 1 1 d . . . C3 C 0.30415(15) 0.38073(19) 0.23282(16) 0.0426(4) Uani 1 1 d . . . C4 C 0.41100(15) 0.36962(19) 0.17363(15) 0.0405(4) Uani 1 1 d . . . C5 C 0.40394(14) 0.25436(18) 0.08580(15) 0.0371(4) Uani 1 1 d . . . C6 C 0.13094(16) 0.3487(2) 0.08777(19) 0.0484(5) Uani 1 1 d . . . C7 C 0.03900(19) 0.2440(3) 0.0385(2) 0.0622(6) Uani 1 1 d . . . C8 C -0.00046(19) 0.1503(3) 0.1474(2) 0.0643(6) Uani 1 1 d . . . C9 C 0.09895(19) 0.0755(3) 0.2138(2) 0.0600(6) Uani 1 1 d . . . C10 C 0.51168(17) 0.4487(2) 0.19153(18) 0.0520(5) Uani 1 1 d . . . C11 C 0.60192(17) 0.4113(2) 0.12184(19) 0.0553(5) Uani 1 1 d . . . C12 C 0.59543(15) 0.2948(2) 0.03309(18) 0.0476(5) Uani 1 1 d . . . C13 C 0.49608(15) 0.2171(2) 0.01480(17) 0.0422(4) Uani 1 1 d . . . C14 C 0.69689(17) 0.2544(3) -0.0411(2) 0.0690(6) Uani 1 1 d . . . H14A H 0.6980 0.1498 -0.0546 0.103 Uiso 1 1 calc R . . H14B H 0.7643 0.2837 0.0061 0.103 Uiso 1 1 calc R . . H14C H 0.6930 0.3038 -0.1222 0.103 Uiso 1 1 calc R . . H1 H 0.2704(17) 0.146(2) 0.011(2) 0.059(6) Uiso 1 1 d . . . H6A H 0.1623(17) 0.403(2) 0.021(2) 0.057(6) Uiso 1 1 d . . . H6B H 0.1001(16) 0.421(2) 0.1449(18) 0.049(5) Uiso 1 1 d . . . H7A H 0.0697(19) 0.183(2) -0.029(2) 0.065(6) Uiso 1 1 d . . . H7B H -0.024(2) 0.303(2) -0.004(2) 0.074(7) Uiso 1 1 d . . . H8A H -0.0389(17) 0.210(2) 0.209(2) 0.059(6) Uiso 1 1 d . . . H8B H -0.055(2) 0.077(3) 0.118(2) 0.079(7) Uiso 1 1 d . . . H9A H 0.0775(18) 0.021(2) 0.287(2) 0.066(6) Uiso 1 1 d . . . H9B H 0.1360(17) 0.006(2) 0.152(2) 0.062(6) Uiso 1 1 d . . . H10 H 0.5145(18) 0.528(3) 0.252(2) 0.068(6) Uiso 1 1 d . . . H11 H 0.6733(19) 0.464(2) 0.1332(19) 0.065(6) Uiso 1 1 d . . . H13 H 0.4885(15) 0.139(2) -0.0446(18) 0.050(5) 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 0.0519(8) 0.0556(8) 0.0424(7) 0.0069(6) 0.0086(6) -0.0084(6) O2 0.0717(9) 0.0591(8) 0.0460(7) -0.0154(6) 0.0119(7) -0.0019(7) N1 0.0409(8) 0.0460(9) 0.0438(9) -0.0098(7) 0.0073(7) -0.0064(7) C2 0.0419(10) 0.0432(9) 0.0342(9) 0.0005(7) 0.0088(7) -0.0009(7) C3 0.0534(11) 0.0414(9) 0.0332(9) 0.0009(7) 0.0036(8) 0.0004(8) C4 0.0467(10) 0.0411(9) 0.0335(9) 0.0022(7) -0.0002(7) -0.0029(8) C5 0.0400(9) 0.0372(9) 0.0340(9) 0.0058(7) 0.0008(7) -0.0006(7) C6 0.0472(11) 0.0541(12) 0.0442(10) 0.0043(9) 0.0057(9) 0.0015(9) C7 0.0456(12) 0.0821(16) 0.0586(13) 0.0016(12) -0.0026(10) -0.0010(11) C8 0.0451(12) 0.0762(16) 0.0722(15) -0.0075(12) 0.0095(11) -0.0139(11) C9 0.0599(13) 0.0582(13) 0.0632(13) 0.0042(11) 0.0175(11) -0.0143(10) C10 0.0578(12) 0.0540(12) 0.0436(11) -0.0021(9) -0.0029(9) -0.0142(9) C11 0.0429(11) 0.0652(13) 0.0571(12) 0.0098(10) -0.0051(9) -0.0148(10) C12 0.0406(10) 0.0512(11) 0.0510(11) 0.0137(9) 0.0035(8) 0.0016(8) C13 0.0451(10) 0.0395(10) 0.0423(10) 0.0037(8) 0.0052(8) 0.0029(8) C14 0.0463(12) 0.0744(15) 0.0875(16) 0.0123(12) 0.0167(11) 0.0026(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.4214(19) . ? O1 C9 1.433(2) . ? O2 C3 1.222(2) . ? N1 C5 1.389(2) . ? N1 C2 1.457(2) . ? C2 C6 1.523(3) . ? C2 C3 1.545(2) . ? C3 C4 1.438(2) . ? C4 C5 1.394(2) . ? C4 C10 1.399(3) . ? C5 C13 1.390(2) . ? C6 C7 1.521(3) . ? C7 C8 1.513(3) . ? C8 C9 1.505(3) . ? C10 C11 1.364(3) . ? C11 C12 1.408(3) . ? C12 C13 1.380(3) . ? C12 C14 1.506(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 O1 C9 112.57(14) . . ? C5 N1 C2 109.04(14) . . ? O1 C2 N1 111.98(14) . . ? O1 C2 C6 111.33(14) . . ? N1 C2 C6 113.33(14) . . ? O1 C2 C3 105.78(13) . . ? N1 C2 C3 103.44(13) . . ? C6 C2 C3 110.42(15) . . ? O2 C3 C4 130.38(17) . . ? O2 C3 C2 122.98(16) . . ? C4 C3 C2 106.63(14) . . ? C5 C4 C10 120.06(17) . . ? C5 C4 C3 107.93(15) . . ? C10 C4 C3 132.00(17) . . ? N1 C5 C13 127.39(16) . . ? N1 C5 C4 111.95(15) . . ? C13 C5 C4 120.62(16) . . ? C7 C6 C2 112.09(17) . . ? C8 C7 C6 109.66(18) . . ? C9 C8 C7 109.90(18) . . ? O1 C9 C8 111.34(19) . . ? C11 C10 C4 119.02(19) . . ? C10 C11 C12 121.21(18) . . ? C13 C12 C11 119.87(18) . . ? C13 C12 C14 120.04(19) . . ? C11 C12 C14 120.08(18) . . ? C12 C13 C5 119.21(18) . . ? 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 C9 O1 C2 N1 -71.24(19) . . . . ? C9 O1 C2 C6 56.8(2) . . . . ? C9 O1 C2 C3 176.76(15) . . . . ? C5 N1 C2 O1 -123.40(15) . . . . ? C5 N1 C2 C6 109.64(17) . . . . ? C5 N1 C2 C3 -9.95(17) . . . . ? O1 C2 C3 O2 -52.1(2) . . . . ? N1 C2 C3 O2 -170.00(16) . . . . ? C6 C2 C3 O2 68.4(2) . . . . ? O1 C2 C3 C4 126.96(14) . . . . ? N1 C2 C3 C4 9.09(17) . . . . ? C6 C2 C3 C4 -112.47(16) . . . . ? O2 C3 C4 C5 173.93(18) . . . . ? C2 C3 C4 C5 -5.07(18) . . . . ? O2 C3 C4 C10 -4.9(3) . . . . ? C2 C3 C4 C10 176.06(18) . . . . ? C2 N1 C5 C13 -174.59(16) . . . . ? C2 N1 C5 C4 7.50(19) . . . . ? C10 C4 C5 N1 177.77(15) . . . . ? C3 C4 C5 N1 -1.25(19) . . . . ? C10 C4 C5 C13 -0.3(3) . . . . ? C3 C4 C5 C13 -179.32(15) . . . . ? O1 C2 C6 C7 -52.4(2) . . . . ? N1 C2 C6 C7 74.9(2) . . . . ? C3 C2 C6 C7 -169.61(16) . . . . ? C2 C6 C7 C8 51.1(2) . . . . ? C6 C7 C8 C9 -53.6(3) . . . . ? C2 O1 C9 C8 -60.7(2) . . . . ? C7 C8 C9 O1 58.6(3) . . . . ? C5 C4 C10 C11 0.1(3) . . . . ? C3 C4 C10 C11 178.84(18) . . . . ? C4 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? C10 C11 C12 C14 -179.08(19) . . . . ? C11 C12 C13 C5 -0.7(3) . . . . ? C14 C12 C13 C5 178.89(17) . . . . ? N1 C5 C13 C12 -177.12(16) . . . . ? C4 C5 C13 C12 0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.262 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.034 # Attachment 'PATEL-OBC-2BD.cif' data_pp1 _database_code_depnum_ccdc_archive 'CCDC 836107' #TrackingRef 'PATEL-OBC-2BD.cif' # start Validation Reply Form _vrf_PLAT029_pp1 ; PROBLEM: _diffn_measured_fraction_theta_full Low.... RESPONSE: This is due to poor quality of the single crystals (very thin needles) which did not diffract to high angle. ; _vrf_REFLT03_pp1 ; PROBLEM: Reflection count < 90% complete (theta max?) RESPONSE: This is due to poor quality of the single crystals (very thin needles) which did not diffract to high angle. ; _vrf_PLAT022_pp1 ; PROBLEM: Ratio Unique / Expected Reflections (too) Low .. 0.880 RESPONSE: This is due to poor quality of the single crystals (very thin needles) which did not diffract to high angle. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 N O4' _chemical_formula_sum 'C14 H15 N O4' _chemical_formula_weight 261.27 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 P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.075(2) _cell_length_b 10.398(4) _cell_length_c 24.245(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.01 _cell_angle_gamma 90.00 _cell_volume 1272.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1030 _cell_measurement_theta_min 2.234 _cell_measurement_theta_max 20.714 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9753 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6487 _diffrn_reflns_av_R_equivalents 0.0831 _diffrn_reflns_av_sigmaI/netI 0.1103 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1966 _reflns_number_gt 1177 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Ortep32' _computing_publication_material SHELXTL _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^)+(0.0321P)^2^+0.0970P] 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 1966 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1332 _refine_ls_R_factor_gt 0.0742 _refine_ls_wR_factor_ref 0.1552 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.6090(5) 0.2329(2) 0.09518(10) 0.0495(7) Uani 1 1 d . . . O2 O 0.7218(7) -0.0310(3) 0.12527(13) 0.0686(9) Uani 1 1 d . . . O3 O 0.0125(8) 0.0030(3) 0.37015(13) 0.0912(12) Uani 1 1 d . . . O4 O -0.1692(8) 0.1747(2) 0.32749(12) 0.0666(10) Uani 1 1 d . . . N1 N 0.2341(7) 0.2011(3) 0.14501(13) 0.0506(9) Uani 1 1 d . . . H1 H 0.1412 0.2697 0.1387 0.061 Uiso 1 1 calc R . . C2 C 0.4069(8) 0.1451(3) 0.10711(16) 0.0434(10) Uani 1 1 d . . . C3 C 0.5509(9) 0.0356(3) 0.14154(18) 0.0500(11) Uani 1 1 d . . . C4 C 0.4314(8) 0.0286(3) 0.19350(16) 0.0434(10) Uani 1 1 d . . . C5 C 0.2418(8) 0.1271(3) 0.19284(15) 0.0416(9) Uani 1 1 d . . . C6 C 0.2563(10) 0.0933(4) 0.05440(16) 0.0561(12) Uani 1 1 d . . . H6A H 0.3718 0.0369 0.0360 0.067 Uiso 1 1 calc R . . H6B H 0.1074 0.0426 0.0641 0.067 Uiso 1 1 calc R . . C7 C 0.1547(11) 0.1985(4) 0.01449(18) 0.0678(13) Uani 1 1 d . . . H7A H 0.0856 0.1608 -0.0207 0.081 Uiso 1 1 calc R . . H7B H 0.0119 0.2446 0.0294 0.081 Uiso 1 1 calc R . . C8 C 0.3755(11) 0.2904(4) 0.00555(18) 0.0671(14) Uani 1 1 d . . . H8A H 0.3051 0.3628 -0.0165 0.080 Uiso 1 1 calc R . . H8B H 0.5054 0.2474 -0.0146 0.080 Uiso 1 1 calc R . . C9 C 0.5078(10) 0.3384(3) 0.06085(16) 0.0580(12) Uani 1 1 d . . . H9A H 0.6520 0.3959 0.0545 0.070 Uiso 1 1 calc R . . H9B H 0.3804 0.3864 0.0798 0.070 Uiso 1 1 calc R . . C10 C 0.4736(9) -0.0546(3) 0.23829(17) 0.0517(11) Uani 1 1 d . . . H10 H 0.5991 -0.1198 0.2385 0.062 Uiso 1 1 calc R . . C11 C 0.3274(9) -0.0392(4) 0.28208(18) 0.0541(11) Uani 1 1 d . . . H11 H 0.3532 -0.0943 0.3124 0.065 Uiso 1 1 calc R . . C12 C 0.1378(9) 0.0600(3) 0.28145(16) 0.0457(10) Uani 1 1 d . . . C13 C 0.0949(8) 0.1436(3) 0.23678(15) 0.0444(10) Uani 1 1 d . . . H13 H -0.0299 0.2092 0.2366 0.053 Uiso 1 1 calc R . . C14 C -0.0080(10) 0.0737(4) 0.33074(18) 0.0528(11) Uani 1 1 d . . . C15 C -0.3074(12) 0.1993(4) 0.37494(19) 0.0801(16) Uani 1 1 d . . . H15A H -0.3807 0.1205 0.3872 0.120 Uiso 1 1 calc R . . H15B H -0.4477 0.2597 0.3652 0.120 Uiso 1 1 calc R . . H15C H -0.1866 0.2343 0.4042 0.120 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 0.0505(18) 0.0441(14) 0.0544(17) 0.0046(12) 0.0078(15) -0.0112(13) O2 0.068(2) 0.0571(17) 0.087(2) 0.0044(15) 0.035(2) 0.0144(17) O3 0.087(3) 0.122(3) 0.068(2) 0.048(2) 0.026(2) 0.034(2) O4 0.098(3) 0.0514(16) 0.0556(19) 0.0008(13) 0.0304(19) 0.0103(17) N1 0.062(2) 0.0442(17) 0.048(2) 0.0098(15) 0.0204(18) 0.0139(16) C2 0.046(2) 0.0407(19) 0.047(3) -0.0001(17) 0.018(2) -0.0069(18) C3 0.049(3) 0.040(2) 0.063(3) -0.0030(18) 0.014(2) -0.0029(19) C4 0.045(2) 0.0380(19) 0.047(2) 0.0011(17) 0.004(2) -0.0029(18) C5 0.044(2) 0.0395(19) 0.043(2) -0.0028(17) 0.009(2) -0.0045(18) C6 0.056(3) 0.062(2) 0.052(3) -0.007(2) 0.016(2) -0.014(2) C7 0.061(3) 0.091(3) 0.051(3) -0.003(2) 0.004(3) -0.007(3) C8 0.072(4) 0.078(3) 0.052(3) 0.012(2) 0.014(3) 0.002(3) C9 0.065(3) 0.045(2) 0.064(3) 0.0098(19) 0.009(3) -0.006(2) C10 0.047(3) 0.046(2) 0.063(3) 0.0039(19) 0.006(2) 0.005(2) C11 0.058(3) 0.049(2) 0.055(3) 0.0118(19) 0.004(2) 0.001(2) C12 0.047(2) 0.048(2) 0.041(2) -0.0017(17) 0.004(2) -0.0090(18) C13 0.047(2) 0.0423(19) 0.044(2) -0.0015(17) 0.006(2) 0.0004(18) C14 0.057(3) 0.050(2) 0.051(3) 0.004(2) 0.005(2) -0.002(2) C15 0.103(5) 0.085(3) 0.058(3) -0.012(2) 0.032(3) 0.008(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 C2 1.426(4) . ? O1 C9 1.438(4) . ? O2 C3 1.208(5) . ? O3 C14 1.202(4) . ? O4 C14 1.328(5) . ? O4 C15 1.432(5) . ? N1 C5 1.389(4) . ? N1 C2 1.457(5) . ? N1 H1 0.8600 . ? C2 C6 1.517(5) . ? C2 C3 1.549(5) . ? C3 C4 1.456(6) . ? C4 C10 1.388(5) . ? C4 C5 1.404(5) . ? C5 C13 1.373(5) . ? C6 C7 1.515(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.505(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.519(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.367(6) . ? C10 H10 0.9300 . ? C11 C12 1.409(6) . ? C11 H11 0.9300 . ? C12 C13 1.389(5) . ? C12 C14 1.477(6) . ? C13 H13 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 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 C2 O1 C9 112.6(3) . . ? C14 O4 C15 116.4(3) . . ? C5 N1 C2 109.8(3) . . ? C5 N1 H1 125.1 . . ? C2 N1 H1 125.1 . . ? O1 C2 N1 111.4(3) . . ? O1 C2 C6 111.5(3) . . ? N1 C2 C6 112.9(4) . . ? O1 C2 C3 105.8(3) . . ? N1 C2 C3 103.6(3) . . ? C6 C2 C3 111.2(3) . . ? O2 C3 C4 129.2(4) . . ? O2 C3 C2 124.0(4) . . ? C4 C3 C2 106.7(3) . . ? C10 C4 C5 120.9(4) . . ? C10 C4 C3 131.6(4) . . ? C5 C4 C3 107.5(3) . . ? C13 C5 N1 127.4(4) . . ? C13 C5 C4 120.6(3) . . ? N1 C5 C4 111.9(4) . . ? C7 C6 C2 112.9(3) . . ? C7 C6 H6A 109.0 . . ? C2 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? C2 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 110.0(4) . . ? C8 C7 H7A 109.7 . . ? C6 C7 H7A 109.7 . . ? C8 C7 H7B 109.7 . . ? C6 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C7 C8 C9 110.4(4) . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? O1 C9 C8 111.0(3) . . ? O1 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? O1 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C4 118.9(4) . . ? C11 C10 H10 120.6 . . ? C4 C10 H10 120.6 . . ? C10 C11 C12 120.2(4) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 121.2(4) . . ? C13 C12 C14 121.3(4) . . ? C11 C12 C14 117.5(4) . . ? C5 C13 C12 118.2(4) . . ? C5 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? O3 C14 O4 122.2(5) . . ? O3 C14 C12 125.1(4) . . ? O4 C14 C12 112.7(3) . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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 C9 O1 C2 N1 -70.8(4) . . . . ? C9 O1 C2 C6 56.3(4) . . . . ? C9 O1 C2 C3 177.3(3) . . . . ? C5 N1 C2 O1 -120.4(3) . . . . ? C5 N1 C2 C6 113.3(3) . . . . ? C5 N1 C2 C3 -7.1(4) . . . . ? O1 C2 C3 O2 -59.3(5) . . . . ? N1 C2 C3 O2 -176.6(4) . . . . ? C6 C2 C3 O2 61.8(5) . . . . ? O1 C2 C3 C4 123.1(3) . . . . ? N1 C2 C3 C4 5.8(4) . . . . ? C6 C2 C3 C4 -115.8(4) . . . . ? O2 C3 C4 C10 -0.9(7) . . . . ? C2 C3 C4 C10 176.6(4) . . . . ? O2 C3 C4 C5 -180.0(4) . . . . ? C2 C3 C4 C5 -2.5(4) . . . . ? C2 N1 C5 C13 -175.8(4) . . . . ? C2 N1 C5 C4 6.1(4) . . . . ? C10 C4 C5 C13 0.4(6) . . . . ? C3 C4 C5 C13 179.6(3) . . . . ? C10 C4 C5 N1 178.8(3) . . . . ? C3 C4 C5 N1 -2.0(4) . . . . ? O1 C2 C6 C7 -51.7(5) . . . . ? N1 C2 C6 C7 74.6(4) . . . . ? C3 C2 C6 C7 -169.4(4) . . . . ? C2 C6 C7 C8 50.2(5) . . . . ? C6 C7 C8 C9 -52.6(5) . . . . ? C2 O1 C9 C8 -60.0(5) . . . . ? C7 C8 C9 O1 57.8(5) . . . . ? C5 C4 C10 C11 -0.1(6) . . . . ? C3 C4 C10 C11 -179.1(4) . . . . ? C4 C10 C11 C12 -0.1(6) . . . . ? C10 C11 C12 C13 0.0(6) . . . . ? C10 C11 C12 C14 -178.3(4) . . . . ? N1 C5 C13 C12 -178.5(4) . . . . ? C4 C5 C13 C12 -0.5(5) . . . . ? C11 C12 C13 C5 0.3(5) . . . . ? C14 C12 C13 C5 178.5(4) . . . . ? C15 O4 C14 O3 3.4(6) . . . . ? C15 O4 C14 C12 -176.7(4) . . . . ? C13 C12 C14 O3 177.6(4) . . . . ? C11 C12 C14 O3 -4.1(6) . . . . ? C13 C12 C14 O4 -2.3(5) . . . . ? C11 C12 C14 O4 176.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.880 _refine_diff_density_max 0.169 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.035