# 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 'Uriel, Santiago' _publ_contact_author_email suriel@unizar.es loop_ _publ_author_name S.Uriel S.Graus J.Serrano data_est10 _database_code_depnum_ccdc_archive 'CCDC 855299' #TrackingRef '- Compound1 revised.CIF' _audit_creation_date ; 'Thu May 21 08:42:02 2009' ; _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET) (compiled Feb 28 2008,12:10:31) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET) (compiled Feb 28 2008,12:10:31) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET) (compiled Feb 28 2008,12:10:31) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET) (compiled Feb 28 2008,12:10:31) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O3' _chemical_formula_weight 260.29 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 Cc 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 7.0111(4) _cell_length_b 10.3913(3) _cell_length_c 17.7538(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.186(6) _cell_angle_gamma 90.00 _cell_volume 1289.99(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_min 0.9743 _exptl_absorpt_correction_T_max 1.0195 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET) (compiled Feb 28 2008,12:10:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.3990 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6677 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2475 _reflns_number_gt 2106 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXTL Bruker' _computing_structure_refinement 'SHELXTL Bruker' _computing_molecular_graphics 'SHELXTL Bruker' _computing_publication_material 'SHELXTL Bruker' _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^)+(0.0292P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.2(9) _refine_ls_number_reflns 2475 _refine_ls_number_parameters 236 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0537 _refine_ls_wR_factor_gt 0.0521 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.927 _refine_ls_shift/su_max 0.002 _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 O1 O 1.55783(16) 0.37632(10) 0.79487(7) 0.0335(3) Uani 1 1 d . . . N1 N 1.3712(2) 0.28934(13) 0.69481(7) 0.0269(3) Uani 1 1 d . . . HN1 H 1.289(2) 0.3505(15) 0.6879(9) 0.021(4) Uiso 1 1 d . . . C1 C 1.5138(2) 0.29182(15) 0.74904(9) 0.0251(4) Uani 1 1 d . . . O2 O 1.59341(17) -0.00622(10) 0.67203(7) 0.0370(3) Uani 1 1 d . . . N2 N 1.6129(2) 0.17639(13) 0.74494(8) 0.0280(4) Uani 1 1 d . . . HN2 H 1.712(3) 0.1602(16) 0.7731(10) 0.033(5) Uiso 1 1 d . . . C2 C 1.5377(2) 0.09965(15) 0.68919(9) 0.0261(4) Uani 1 1 d . . . O3 O 0.46487(15) 0.38299(12) 0.32543(6) 0.0294(3) Uani 1 1 d . . . HO3 H 0.489(3) 0.461(2) 0.3169(11) 0.050(6) Uiso 1 1 d . . . C3 C 1.3717(2) 0.17344(13) 0.64869(8) 0.0226(4) Uani 1 1 d . . . C4 C 1.4237(2) 0.20237(17) 0.56800(10) 0.0278(4) Uani 1 1 d . . . H4B H 1.452(2) 0.1211(17) 0.5472(9) 0.025(4) Uiso 1 1 d . . . H4A H 1.541(3) 0.2577(17) 0.5716(10) 0.034(5) Uiso 1 1 d . . . C5 C 1.2596(2) 0.26723(17) 0.52196(10) 0.0273(4) Uani 1 1 d . . . H5B H 1.239(2) 0.3556(18) 0.5465(9) 0.033(4) Uiso 1 1 d . . . H5A H 1.303(2) 0.2842(15) 0.4722(10) 0.029(4) Uiso 1 1 d . . . C6 C 1.0792(2) 0.18564(15) 0.51955(9) 0.0230(4) Uani 1 1 d . . . H6A H 1.113(2) 0.1030(15) 0.4992(8) 0.016(4) Uiso 1 1 d . . . C7 C 1.0223(2) 0.16308(16) 0.60028(9) 0.0252(4) Uani 1 1 d . . . H7B H 0.907(3) 0.1141(16) 0.6001(8) 0.028(5) Uiso 1 1 d . . . H7A H 0.986(2) 0.2474(17) 0.6234(8) 0.026(4) Uiso 1 1 d . . . C8 C 1.1857(2) 0.09737(17) 0.64783(10) 0.0266(4) Uani 1 1 d . . . H8B H 1.215(2) 0.0118(17) 0.6270(9) 0.028(4) Uiso 1 1 d . . . H8A H 1.149(3) 0.0895(17) 0.6999(11) 0.040(5) Uiso 1 1 d . . . C9 C 0.9161(2) 0.23970(15) 0.46769(8) 0.0216(3) Uani 1 1 d . . . C10 C 0.9008(2) 0.36988(15) 0.45157(9) 0.0284(4) Uani 1 1 d . . . H10 H 0.990(2) 0.4265(16) 0.4744(9) 0.026(4) Uiso 1 1 d . . . C11 C 0.7533(2) 0.41896(16) 0.40411(9) 0.0265(4) Uani 1 1 d . . . H11 H 0.743(2) 0.5098(16) 0.3909(8) 0.019(4) Uiso 1 1 d . . . C12 C 0.6155(2) 0.33692(14) 0.37185(8) 0.0222(3) Uani 1 1 d . . . C13 C 0.6279(2) 0.20617(14) 0.38561(9) 0.0270(4) Uani 1 1 d . . . H13 H 0.526(2) 0.1495(16) 0.3597(9) 0.027(4) Uiso 1 1 d . . . C14 C 0.7778(2) 0.15897(16) 0.43313(9) 0.0253(4) Uani 1 1 d . . . H14 H 0.788(2) 0.0641(18) 0.4427(9) 0.028(4) 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 0.0360(7) 0.0280(6) 0.0352(7) -0.0099(6) -0.0071(5) 0.0032(5) N1 0.0262(8) 0.0227(7) 0.0304(8) -0.0051(6) -0.0085(6) 0.0110(6) C1 0.0225(9) 0.0243(8) 0.0280(9) -0.0003(7) -0.0021(7) 0.0026(7) O2 0.0361(7) 0.0263(7) 0.0466(8) -0.0081(5) -0.0105(6) 0.0138(5) N2 0.0220(8) 0.0291(8) 0.0310(9) -0.0026(6) -0.0114(7) 0.0084(6) C2 0.0236(10) 0.0261(9) 0.0279(10) 0.0004(7) -0.0035(7) 0.0055(7) O3 0.0234(7) 0.0300(7) 0.0329(6) 0.0075(5) -0.0120(5) -0.0058(5) C3 0.0219(9) 0.0207(7) 0.0243(10) -0.0012(6) -0.0048(7) 0.0064(7) C4 0.0199(9) 0.0327(10) 0.0306(10) -0.0010(8) 0.0002(7) 0.0031(8) C5 0.0223(9) 0.0389(10) 0.0205(10) 0.0049(8) -0.0007(7) -0.0001(8) C6 0.0210(9) 0.0220(8) 0.0255(9) -0.0026(7) -0.0013(7) 0.0046(7) C7 0.0194(9) 0.0275(9) 0.0282(9) 0.0040(7) -0.0014(7) -0.0006(7) C8 0.0257(9) 0.0257(9) 0.0277(10) 0.0036(7) -0.0035(7) 0.0016(7) C9 0.0217(9) 0.0246(8) 0.0181(8) -0.0025(7) 0.0002(6) 0.0026(7) C10 0.0257(10) 0.0252(9) 0.0325(10) -0.0042(7) -0.0108(8) -0.0012(8) C11 0.0285(10) 0.0223(8) 0.0278(9) -0.0016(7) -0.0048(7) 0.0014(7) C12 0.0183(8) 0.0303(8) 0.0177(8) 0.0015(7) -0.0008(6) -0.0005(7) C13 0.0236(9) 0.0279(8) 0.0286(9) -0.0004(8) -0.0042(7) -0.0065(8) C14 0.0250(9) 0.0222(8) 0.0288(9) 0.0017(7) 0.0022(7) -0.0009(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2213(18) . ? N1 C1 1.337(2) . ? N1 C3 1.4566(19) . ? C1 N2 1.391(2) . ? O2 C2 1.2135(17) . ? N2 C2 1.348(2) . ? C2 C3 1.529(2) . ? O3 C12 1.3770(18) . ? C3 C8 1.524(2) . ? C3 C4 1.533(2) . ? C4 C5 1.519(2) . ? C5 C6 1.521(2) . ? C6 C9 1.522(2) . ? C6 C7 1.534(2) . ? C7 C8 1.533(2) . ? C9 C10 1.385(2) . ? C9 C14 1.390(2) . ? C10 C11 1.383(2) . ? C11 C12 1.381(2) . ? C12 C13 1.382(2) . ? C13 C14 1.388(2) . ? 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 N1 C3 112.85(13) . . ? O1 C1 N1 129.28(15) . . ? O1 C1 N2 123.51(15) . . ? N1 C1 N2 107.21(13) . . ? C2 N2 C1 112.26(13) . . ? O2 C2 N2 127.23(14) . . ? O2 C2 C3 125.76(14) . . ? N2 C2 C3 106.97(12) . . ? N1 C3 C8 113.40(14) . . ? N1 C3 C2 100.57(11) . . ? C8 C3 C2 111.47(12) . . ? N1 C3 C4 111.94(13) . . ? C8 C3 C4 110.72(13) . . ? C2 C3 C4 108.24(12) . . ? C5 C4 C3 111.56(13) . . ? C4 C5 C6 111.30(14) . . ? C5 C6 C9 113.45(13) . . ? C5 C6 C7 109.37(13) . . ? C9 C6 C7 112.73(13) . . ? C8 C7 C6 110.34(14) . . ? C3 C8 C7 112.28(13) . . ? C10 C9 C14 117.19(14) . . ? C10 C9 C6 121.93(14) . . ? C14 C9 C6 120.87(14) . . ? C11 C10 C9 121.96(15) . . ? C12 C11 C10 119.63(15) . . ? O3 C12 C11 121.08(14) . . ? O3 C12 C13 118.91(13) . . ? C11 C12 C13 120.01(14) . . ? C12 C13 C14 119.35(14) . . ? C13 C14 C9 121.84(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.130 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.029 # Attachment '- compound2 revised.CIF' data_est8 _database_code_depnum_ccdc_archive 'CCDC 855300' #TrackingRef '- compound2 revised.CIF' _audit_creation_date ; 'Tue May 19 11:45:32 2009' ; _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET) (compiled Feb 28 2008,12:10:31) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET) (compiled Feb 28 2008,12:10:31) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET) (compiled Feb 28 2008,12:10:31) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET) (compiled Feb 28 2008,12:10:31) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 N2 O3' _chemical_formula_weight 274.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C2/c 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 36.189(5) _cell_length_b 7.5131(5) _cell_length_c 10.3712(16) _cell_angle_alpha 90.00 _cell_angle_beta 102.949(13) _cell_angle_gamma 90.00 _cell_volume 2748.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 1.0210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET) (compiled Feb 28 2008,12:10:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.3990 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23495 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2798 _reflns_number_gt 2238 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXTL Bruker' _computing_structure_refinement 'SHELXTL Bruker' _computing_molecular_graphics 'SHELXTL Bruker' _computing_publication_material 'SHELXTL Bruker' _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^)+(0.0501P)^2^+0.5044P] 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 2798 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0837 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.005 _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 O1 O -0.03341(2) 0.29244(11) 0.86062(8) 0.0270(2) Uani 1 1 d . . . N1 N 0.03211(3) 0.28274(14) 0.91441(10) 0.0250(2) Uani 1 1 d . . . HN1 H 0.0359(4) 0.2841(18) 0.8318(16) 0.036(4) Uiso 1 1 d . . . C1 C -0.00262(3) 0.28370(15) 0.93909(11) 0.0219(2) Uani 1 1 d . . . O2 O 0.05184(2) 0.26378(12) 1.25848(8) 0.0310(2) Uani 1 1 d . . . C2 C 0.03924(3) 0.26712(16) 1.13914(11) 0.0236(3) Uani 1 1 d . . . N2 N 0.00196(3) 0.27436(13) 1.07614(9) 0.0238(2) Uani 1 1 d . . . HN2 H -0.0172(4) 0.2747(18) 1.1139(15) 0.035(4) Uiso 1 1 d . . . O3 O 0.24004(2) 0.17161(12) 0.62264(9) 0.0326(2) Uani 1 1 d . . . C3 C 0.06223(3) 0.25969(15) 1.03299(11) 0.0224(3) Uani 1 1 d . . . C4 C 0.09207(3) 0.40721(17) 1.05094(12) 0.0269(3) Uani 1 1 d . . . H4B H 0.0793(3) 0.5239(18) 1.0438(12) 0.029(3) Uiso 1 1 d . . . H4A H 0.1080(4) 0.3957(17) 1.1418(13) 0.027(3) Uiso 1 1 d . . . C5 C 0.11718(3) 0.39116(16) 0.95173(13) 0.0271(3) Uani 1 1 d . . . H5B H 0.1018(4) 0.4123(19) 0.8593(13) 0.033(4) Uiso 1 1 d . . . H5A H 0.1371(4) 0.4826(19) 0.9715(13) 0.034(3) Uiso 1 1 d . . . C6 C 0.13614(3) 0.20815(16) 0.95846(11) 0.0227(3) Uani 1 1 d . . . H6A H 0.1509(4) 0.1885(17) 1.0500(13) 0.027(3) Uiso 1 1 d . . . C7 C 0.10530(3) 0.06453(16) 0.93348(12) 0.0237(3) Uani 1 1 d . . . H7B H 0.0892(3) 0.0732(17) 0.8423(12) 0.025(3) Uiso 1 1 d . . . H7A H 0.1172(4) -0.0551(19) 0.9375(12) 0.031(3) Uiso 1 1 d . . . C8 C 0.08093(3) 0.07631(16) 1.03506(12) 0.0257(3) Uani 1 1 d . . . H8B H 0.0609(4) -0.0149(17) 1.0211(12) 0.030(3) Uiso 1 1 d . . . H8A H 0.0973(4) 0.0559(17) 1.1250(13) 0.030(3) Uiso 1 1 d . . . C9 C 0.16352(3) 0.19205(15) 0.86900(11) 0.0220(3) Uani 1 1 d . . . C10 C 0.20084(3) 0.14301(17) 0.91943(12) 0.0281(3) Uani 1 1 d . . . H10 H 0.2087(4) 0.1138(18) 1.0132(14) 0.037(4) Uiso 1 1 d . . . C11 C 0.22735(3) 0.13088(17) 0.84155(13) 0.0295(3) Uani 1 1 d . . . H11 H 0.2526(4) 0.0953(18) 0.8813(13) 0.034(3) Uiso 1 1 d . . . C12 C 0.21643(3) 0.17071(15) 0.70872(12) 0.0239(3) Uani 1 1 d . . . C13 C 0.17879(3) 0.21481(16) 0.65454(13) 0.0271(3) Uani 1 1 d . . . H13 H 0.1714(4) 0.2426(17) 0.5605(15) 0.034(4) Uiso 1 1 d . . . C14 C 0.15283(3) 0.22576(16) 0.73335(12) 0.0251(3) Uani 1 1 d . . . H14 H 0.1274(4) 0.2577(17) 0.6950(13) 0.028(3) Uiso 1 1 d . . . C15 C 0.27943(4) 0.1439(2) 0.67522(16) 0.0379(3) Uani 1 1 d . . . H15C H 0.2896(5) 0.241(2) 0.7457(17) 0.058(5) Uiso 1 1 d . . . H15B H 0.2914(4) 0.156(2) 0.6006(16) 0.050(4) Uiso 1 1 d . . . H15A H 0.2844(4) 0.027(3) 0.7152(16) 0.063(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 0.0221(4) 0.0421(5) 0.0175(4) -0.0011(3) 0.0059(3) -0.0001(3) N1 0.0219(5) 0.0408(6) 0.0139(5) 0.0012(4) 0.0076(4) 0.0007(4) C1 0.0240(6) 0.0262(6) 0.0172(6) -0.0009(5) 0.0084(5) -0.0002(4) O2 0.0258(4) 0.0531(6) 0.0152(5) 0.0005(4) 0.0070(3) 0.0027(4) C2 0.0241(6) 0.0302(6) 0.0177(6) -0.0002(4) 0.0073(5) 0.0009(4) N2 0.0205(5) 0.0378(6) 0.0155(5) -0.0010(4) 0.0095(4) -0.0013(4) O3 0.0270(4) 0.0437(5) 0.0317(5) -0.0034(4) 0.0164(4) -0.0030(4) C3 0.0214(5) 0.0319(6) 0.0153(6) -0.0001(4) 0.0073(4) -0.0002(4) C4 0.0260(6) 0.0297(7) 0.0271(7) -0.0064(5) 0.0106(5) -0.0009(5) C5 0.0280(6) 0.0255(6) 0.0315(7) -0.0050(5) 0.0148(5) -0.0050(5) C6 0.0205(5) 0.0310(6) 0.0172(6) -0.0011(5) 0.0054(5) -0.0004(4) C7 0.0251(6) 0.0244(6) 0.0236(7) -0.0011(5) 0.0093(5) -0.0003(5) C8 0.0265(6) 0.0291(6) 0.0238(7) 0.0022(5) 0.0102(5) -0.0016(5) C9 0.0217(5) 0.0230(6) 0.0226(6) -0.0019(4) 0.0080(5) -0.0019(4) C10 0.0249(6) 0.0362(7) 0.0244(7) 0.0068(5) 0.0076(5) 0.0033(5) C11 0.0219(6) 0.0353(7) 0.0324(7) 0.0073(5) 0.0082(5) 0.0058(5) C12 0.0248(6) 0.0225(6) 0.0283(7) -0.0030(5) 0.0141(5) -0.0025(4) C13 0.0283(6) 0.0328(7) 0.0208(7) -0.0007(5) 0.0070(5) -0.0029(5) C14 0.0202(6) 0.0326(6) 0.0225(6) -0.0012(5) 0.0046(5) 0.0007(5) C15 0.0290(7) 0.0426(8) 0.0484(9) 0.0116(7) 0.0221(6) 0.0077(6) _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 1.2254(14) . ? N1 C1 1.3378(14) . ? N1 C3 1.4593(15) . ? C1 N2 1.3955(15) . ? O2 C2 1.2196(14) . ? C2 N2 1.3619(15) . ? C2 C3 1.5224(16) . ? O3 C12 1.3671(14) . ? O3 C15 1.4229(15) . ? C3 C4 1.5293(16) . ? C3 C8 1.5330(16) . ? C4 C5 1.5225(17) . ? C5 C6 1.5313(16) . ? C6 C9 1.5064(15) . ? C6 C7 1.5322(16) . ? C7 C8 1.5205(16) . ? C9 C10 1.3844(15) . ? C9 C14 1.3961(16) . ? C10 C11 1.3886(17) . ? C11 C12 1.3782(18) . ? C12 C13 1.3923(17) . ? C13 C14 1.3790(17) . ? 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 N1 C3 113.31(10) . . ? O1 C1 N1 128.81(11) . . ? O1 C1 N2 124.20(10) . . ? N1 C1 N2 106.99(10) . . ? O2 C2 N2 126.34(11) . . ? O2 C2 C3 126.33(10) . . ? N2 C2 C3 107.32(10) . . ? C2 N2 C1 111.69(9) . . ? C12 O3 C15 117.91(10) . . ? N1 C3 C2 100.32(9) . . ? N1 C3 C4 112.97(10) . . ? C2 C3 C4 111.76(9) . . ? N1 C3 C8 111.25(9) . . ? C2 C3 C8 109.50(9) . . ? C4 C3 C8 110.62(9) . . ? C5 C4 C3 111.86(10) . . ? C4 C5 C6 111.69(10) . . ? C9 C6 C5 113.20(10) . . ? C9 C6 C7 113.21(9) . . ? C5 C6 C7 108.82(9) . . ? C8 C7 C6 110.83(10) . . ? C7 C8 C3 111.43(10) . . ? C10 C9 C14 117.11(11) . . ? C10 C9 C6 120.62(10) . . ? C14 C9 C6 122.28(10) . . ? C9 C10 C11 122.70(11) . . ? C12 C11 C10 119.11(11) . . ? O3 C12 C11 124.94(10) . . ? O3 C12 C13 115.68(11) . . ? C11 C12 C13 119.37(11) . . ? C14 C13 C12 120.66(11) . . ? C13 C14 C9 120.98(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.219 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.034 # Attachment '- compund5 revised.CIF' data_est _database_code_depnum_ccdc_archive 'CCDC 855301' #TrackingRef '- compund5 revised.CIF' _audit_creation_date ; 'Fri Feb 08 16:52:54 2008' ; _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 N2 O6' _chemical_formula_weight 348.35 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' O O 0.0106 0.0060 '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' _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 7.823(3) _cell_length_b 9.608(5) _cell_length_c 12.6865(15) _cell_angle_alpha 102.052(7) _cell_angle_beta 90.957(17) _cell_angle_gamma 113.86(2) _cell_volume 847.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_min 0.9506 _exptl_absorpt_correction_T_max 1.0375 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur Oxford Diffraction' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.3990 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15532 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_sigmaI/netI 0.1294 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3401 _reflns_number_gt 1458 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXTL Bruker' _computing_structure_refinement 'SHELXTL Bruker' _computing_molecular_graphics 'SHELXTL Bruker' _computing_publication_material 'SHELXTL Bruker' _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^)+(0.0172P)^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 3401 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1358 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0594 _refine_ls_wR_factor_gt 0.0506 _refine_ls_goodness_of_fit_ref 0.772 _refine_ls_restrained_S_all 0.772 _refine_ls_shift/su_max 0.002 _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 0.82673(19) 0.51283(17) 0.59410(10) 0.0571(4) Uani 1 1 d . . . N1 N 0.7736(2) 0.3643(2) 0.42006(13) 0.0420(5) Uani 1 1 d . . . HN1 H 0.895(3) 0.398(2) 0.4055(14) 0.056(7) Uiso 1 1 d . . . C1 C 0.7257(3) 0.4093(3) 0.51809(18) 0.0430(6) Uani 1 1 d . . . O2 O 0.3074(2) 0.1027(2) 0.40271(12) 0.0975(7) Uani 1 1 d . . . N2 N 0.5378(2) 0.3145(2) 0.51838(15) 0.0551(6) Uani 1 1 d . . . HN2 H 0.478(3) 0.320(3) 0.5752(18) 0.092(9) Uiso 1 1 d . . . C2 C 0.4647(3) 0.2042(3) 0.42356(18) 0.0578(7) Uani 1 1 d . . . O3 O 0.91742(16) 0.19175(16) 0.07810(10) 0.0508(4) Uani 1 1 d . . . O4 O 0.7253(2) 0.10730(18) -0.07642(10) 0.0604(5) Uani 1 1 d . . . C3 C 0.6200(3) 0.2322(2) 0.34993(15) 0.0404(6) Uani 1 1 d . . . C4 C 0.6658(4) 0.0908(3) 0.31705(19) 0.0513(7) Uani 1 1 d . . . H4B H 0.550(2) 0.002(2) 0.2830(12) 0.041(6) Uiso 1 1 d . . . H4A H 0.703(2) 0.067(2) 0.3800(13) 0.048(6) Uiso 1 1 d . . . O5 O 1.21557(17) 0.27948(16) -0.34553(10) 0.0479(4) Uani 1 1 d . . . C5 C 0.8188(3) 0.1200(3) 0.24116(18) 0.0468(6) Uani 1 1 d . . . H5A H 0.945(2) 0.215(2) 0.2784(13) 0.051(6) Uiso 1 1 d . . . H5B H 0.849(2) 0.032(2) 0.2241(13) 0.045(6) Uiso 1 1 d . . . O6 O 1.53099(18) 0.36217(16) -0.23902(9) 0.0510(4) Uani 1 1 d . . . C6 C 0.7589(3) 0.1588(3) 0.14238(17) 0.0432(6) Uani 1 1 d . . . H6 H 0.652(2) 0.069(2) 0.1022(13) 0.046(6) Uiso 1 1 d . . . C7 C 0.7165(3) 0.3000(3) 0.17227(19) 0.0478(6) Uani 1 1 d . . . H7B H 0.831(2) 0.387(2) 0.2086(12) 0.044(6) Uiso 1 1 d . . . H7A H 0.673(2) 0.324(2) 0.1099(15) 0.062(7) Uiso 1 1 d . . . C8 C 0.5655(3) 0.2751(3) 0.24967(18) 0.0508(7) Uani 1 1 d . . . H8B H 0.455(3) 0.193(2) 0.2137(13) 0.055(7) Uiso 1 1 d . . . H8A H 0.537(2) 0.371(2) 0.2715(14) 0.061(7) Uiso 1 1 d . . . C9\'I C 0.8801(3) 0.1612(2) -0.02994(17) 0.0414(6) Uani 1 1 d . . . C10 C 1.0559(3) 0.2098(2) -0.08251(15) 0.0357(5) Uani 1 1 d . . . C11 C 1.0463(3) 0.2168(2) -0.19059(16) 0.0361(5) Uani 1 1 d . . . H11 H 0.929(2) 0.1865(17) -0.2272(10) 0.022(5) Uiso 1 1 d . . . C12 C 1.2064(3) 0.2673(2) -0.24031(15) 0.0349(5) Uani 1 1 d . . . C13 C 1.3804(3) 0.3110(2) -0.18265(15) 0.0380(5) Uani 1 1 d . . . C14 C 1.3896(3) 0.2985(3) -0.07704(17) 0.0515(7) Uani 1 1 d . . . H14 H 1.511(2) 0.3259(19) -0.0366(12) 0.046(6) Uiso 1 1 d . . . C15 C 1.2272(3) 0.2489(3) -0.02727(17) 0.0491(7) Uani 1 1 d . . . H15 H 1.231(2) 0.2365(19) 0.0447(13) 0.041(6) Uiso 1 1 d . . . C16 C 1.0429(3) 0.2252(4) -0.4127(2) 0.0553(7) Uani 1 1 d . . . H16C H 1.080(2) 0.242(2) -0.4817(14) 0.052(6) Uiso 1 1 d . . . H16B H 0.972(3) 0.292(2) -0.3833(15) 0.083(8) Uiso 1 1 d . . . H16A H 0.962(3) 0.116(2) -0.4115(14) 0.068(8) Uiso 1 1 d . . . C17 C 1.7121(3) 0.4012(5) -0.1848(2) 0.0691(8) Uani 1 1 d . . . H17C H 1.797(3) 0.437(2) -0.2379(15) 0.073(7) Uiso 1 1 d . . . H17B H 1.709(3) 0.308(3) -0.1631(19) 0.114(12) Uiso 1 1 d . . . H17A H 1.742(4) 0.493(3) -0.123(2) 0.140(13) 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 0.0442(9) 0.0600(11) 0.0360(9) -0.0091(9) 0.0090(7) 0.0002(9) N1 0.0316(11) 0.0470(13) 0.0287(11) -0.0024(9) 0.0114(9) 0.0029(10) C1 0.0387(15) 0.0436(16) 0.0352(15) 0.0049(12) 0.0124(12) 0.0075(13) O2 0.0512(11) 0.0945(15) 0.0708(11) -0.0252(10) 0.0278(9) -0.0248(10) N2 0.0387(12) 0.0592(14) 0.0368(12) -0.0057(11) 0.0192(10) -0.0025(10) C2 0.0414(15) 0.0545(18) 0.0456(15) -0.0060(14) 0.0138(12) -0.0037(13) O3 0.0380(9) 0.0698(12) 0.0305(9) 0.0055(8) 0.0125(6) 0.0114(8) O4 0.0380(10) 0.0884(13) 0.0373(9) 0.0085(8) 0.0049(7) 0.0118(9) C3 0.0314(12) 0.0425(15) 0.0288(13) -0.0016(11) 0.0088(10) 0.0017(11) C4 0.0613(18) 0.0414(18) 0.0386(16) 0.0093(14) 0.0146(13) 0.0087(15) O5 0.0364(9) 0.0720(11) 0.0331(9) 0.0201(8) 0.0080(7) 0.0164(8) C5 0.0591(17) 0.0430(17) 0.0448(16) 0.0130(13) 0.0212(13) 0.0261(15) O6 0.0324(9) 0.0741(12) 0.0457(8) 0.0189(8) 0.0130(7) 0.0188(8) C6 0.0365(14) 0.0506(17) 0.0292(13) 0.0041(12) 0.0128(11) 0.0072(13) C7 0.0493(16) 0.063(2) 0.0343(15) 0.0181(14) 0.0073(12) 0.0235(15) C8 0.0392(15) 0.063(2) 0.0406(15) -0.0002(14) 0.0041(12) 0.0180(15) C9\'I 0.0458(15) 0.0471(16) 0.0273(14) 0.0072(11) 0.0092(11) 0.0159(13) C10 0.0349(13) 0.0433(15) 0.0273(12) 0.0059(11) 0.0104(10) 0.0155(11) C11 0.0304(14) 0.0431(15) 0.0341(14) 0.0071(11) 0.0041(11) 0.0156(12) C12 0.0372(13) 0.0415(15) 0.0289(13) 0.0103(11) 0.0082(10) 0.0181(11) C13 0.0343(13) 0.0469(16) 0.0341(14) 0.0109(12) 0.0139(10) 0.0173(12) C14 0.0347(14) 0.0823(19) 0.0368(14) 0.0160(13) 0.0053(12) 0.0226(14) C15 0.0473(15) 0.075(2) 0.0277(14) 0.0176(13) 0.0104(11) 0.0258(14) C16 0.0432(16) 0.080(2) 0.0356(16) 0.0186(16) 0.0074(12) 0.0162(16) C17 0.0356(16) 0.108(3) 0.065(2) 0.031(2) 0.0155(14) 0.0260(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.217(2) . ? N1 C1 1.340(2) . ? N1 C3 1.451(2) . ? C1 N2 1.381(2) . ? O2 C2 1.203(2) . ? N2 C2 1.361(2) . ? C2 C3 1.517(2) . ? O3 C9\'I 1.341(2) . ? O3 C6 1.458(2) . ? O4 C9\'I 1.193(2) . ? C3 C4 1.520(3) . ? C3 C8 1.521(3) . ? C4 C5 1.522(3) . ? O5 C12 1.3647(18) . ? O5 C16 1.425(2) . ? C5 C6 1.498(3) . ? O6 C13 1.3593(19) . ? O6 C17 1.432(3) . ? C6 C7 1.499(3) . ? C7 C8 1.525(3) . ? C9\'I C10 1.482(3) . ? C10 C15 1.371(2) . ? C10 C11 1.389(2) . ? C11 C12 1.365(2) . ? C12 C13 1.393(2) . ? C13 C14 1.373(2) . ? C14 C15 1.380(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 C1 N1 C3 112.92(17) . . ? O1 C1 N1 127.34(19) . . ? O1 C1 N2 125.4(2) . . ? N1 C1 N2 107.21(19) . . ? C2 N2 C1 111.98(18) . . ? O2 C2 N2 126.45(18) . . ? O2 C2 C3 126.6(2) . . ? N2 C2 C3 106.98(19) . . ? C9\'I O3 C6 117.81(16) . . ? N1 C3 C2 100.85(16) . . ? N1 C3 C4 111.89(18) . . ? C2 C3 C4 111.94(18) . . ? N1 C3 C8 111.55(19) . . ? C2 C3 C8 110.17(17) . . ? C4 C3 C8 110.15(18) . . ? C3 C4 C5 111.1(2) . . ? C12 O5 C16 117.75(15) . . ? C6 C5 C4 110.2(2) . . ? C13 O6 C17 117.23(17) . . ? O3 C6 C5 105.90(17) . . ? O3 C6 C7 109.64(18) . . ? C5 C6 C7 111.24(19) . . ? C6 C7 C8 110.7(2) . . ? C3 C8 C7 111.61(19) . . ? O4 C9\'I O3 123.96(17) . . ? O4 C9\'I C10 124.9(2) . . ? O3 C9\'I C10 111.08(19) . . ? C15 C10 C11 119.31(18) . . ? C15 C10 C9\'I 121.83(19) . . ? C11 C10 C9\'I 118.86(19) . . ? C12 C11 C10 120.4(2) . . ? O5 C12 C11 126.01(18) . . ? O5 C12 C13 114.14(16) . . ? C11 C12 C13 119.86(18) . . ? O6 C13 C14 124.99(19) . . ? O6 C13 C12 115.18(17) . . ? C14 C13 C12 119.82(18) . . ? C13 C14 C15 119.8(2) . . ? C10 C15 C14 120.7(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.121 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.032 # Attachment '- compound3 revised.CIF' data_strz71 _database_code_depnum_ccdc_archive 'CCDC 855302' #TrackingRef '- compound3 revised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 N2 O5.50' _chemical_formula_weight 327.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C2/c 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 20.003(4) _cell_length_b 13.847(3) _cell_length_c 12.636(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.540(10) _cell_angle_gamma 90.00 _cell_volume 3208.7(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2643 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2358 _reflns_number_gt 1645 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0602P)^2^+4.9889P] 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 2358 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 N1 N 0.20762(16) 0.04444(17) 0.6003(2) 0.0375(7) Uani 1 1 d . . . HN1 H 0.204(2) 0.035(3) 0.664(3) 0.058(11) Uiso 1 1 d . . . O1 O 0.25034(14) 0.20226(14) 0.63074(18) 0.0482(7) Uani 1 1 d . . . C1 C 0.22910(18) 0.1291(2) 0.5706(2) 0.0370(8) Uani 1 1 d . . . N2 N 0.22404(16) 0.11941(18) 0.4575(2) 0.0407(7) Uani 1 1 d . . . HN2 H 0.237(2) 0.170(3) 0.427(3) 0.068(12) Uiso 1 1 d . . . O2 O 0.19101(14) -0.00117(15) 0.31815(18) 0.0515(7) Uani 1 1 d . . . C2 C 0.19969(18) 0.0295(2) 0.4135(2) 0.0364(8) Uani 1 1 d . . . O3 O 0.09643(13) -0.25850(14) 0.49146(18) 0.0453(6) Uani 1 1 d . . . C3 C 0.18275(17) -0.02530(19) 0.5047(2) 0.0310(7) Uani 1 1 d . . . O4 O 0.07002(17) -0.72161(17) 0.4786(2) 0.0701(8) Uani 1 1 d . . . C4 C 0.2238(2) -0.1222(2) 0.5385(3) 0.0351(8) Uani 1 1 d . . . H4B H 0.2765(19) -0.111(2) 0.571(2) 0.033(9) Uiso 1 1 d . . . H4A H 0.2106(17) -0.159(2) 0.466(3) 0.042(9) Uiso 1 1 d . . . O5 O 0.10280(14) -0.68621(15) 0.6661(2) 0.0546(7) Uani 1 1 d . . . C5 C 0.20468(19) -0.1763(2) 0.6285(3) 0.0369(8) Uani 1 1 d . . . H5B H 0.2307(17) -0.240(2) 0.647(3) 0.046(9) Uiso 1 1 d . . . H5A H 0.2235(15) -0.138(2) 0.702(2) 0.033(8) Uiso 1 1 d . . . C6 C 0.1225(2) -0.1910(2) 0.5891(3) 0.0399(9) Uani 1 1 d . . . H6 H 0.1104(18) -0.220(2) 0.652(3) 0.058(10) Uiso 1 1 d . . . C7 C 0.0795(2) -0.0976(2) 0.5478(3) 0.0420(9) Uani 1 1 d . . . H7B H 0.0878(15) -0.054(2) 0.613(3) 0.030(7) Uiso 1 1 d . . . H7A H 0.025(2) -0.113(3) 0.514(3) 0.070(13) Uiso 1 1 d . . . C8 C 0.09979(19) -0.0426(2) 0.4590(3) 0.0396(8) Uani 1 1 d . . . H8B H 0.0702(18) 0.021(3) 0.436(3) 0.056(10) Uiso 1 1 d . . . H8A H 0.0856(19) -0.075(2) 0.387(3) 0.057(10) Uiso 1 1 d . . . C9 C 0.09984(18) -0.3563(2) 0.5145(3) 0.0383(8) Uani 1 1 d . . . C10 C 0.07603(19) -0.4167(2) 0.4181(3) 0.0419(9) Uani 1 1 d . . . H10 H 0.0602(19) -0.390(3) 0.342(3) 0.061(11) Uiso 1 1 d . . . C11 C 0.07375(19) -0.5164(2) 0.4322(3) 0.0435(9) Uani 1 1 d . . . H11 H 0.0566(18) -0.557(2) 0.360(3) 0.056(10) Uiso 1 1 d . . . C12 C 0.09561(18) -0.5567(2) 0.5428(3) 0.0389(8) Uani 1 1 d . . . C13 C 0.1206(2) -0.4957(2) 0.6374(3) 0.0485(9) Uani 1 1 d . . . H13 H 0.137(2) -0.524(3) 0.716(3) 0.069(11) Uiso 1 1 d . . . C14 C 0.1241(2) -0.3958(2) 0.6251(3) 0.0488(10) Uani 1 1 d . . . H14 H 0.1460(19) -0.354(3) 0.699(3) 0.061(10) Uiso 1 1 d . . . C15 C 0.08825(19) -0.6629(2) 0.5560(3) 0.0457(9) Uani 1 1 d . . . C16 C 0.0952(2) -0.7863(2) 0.6923(3) 0.0629(11) Uani 1 1 d . . . H16C H 0.1070 -0.7930 0.7734 0.094 Uiso 1 1 calc R . . H16B H 0.1276 -0.8255 0.6713 0.094 Uiso 1 1 calc R . . H16A H 0.0458 -0.8068 0.6494 0.094 Uiso 1 1 calc R . . O10 O 0.5000 -0.6816(5) 0.7500 0.164(3) Uiso 1 2 d S . . HO1 H 0.4738 -0.7032 0.6703 0.181 Uiso 0.50 1 d PR . . HO2 H 0.4600 -0.6873 0.7356 0.181 Uiso 0.50 1 d PR . . 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 N1 0.063(2) 0.0260(12) 0.0321(14) -0.0011(11) 0.0278(14) -0.0089(12) O1 0.0783(18) 0.0288(11) 0.0394(12) -0.0070(9) 0.0255(12) -0.0172(11) C1 0.052(2) 0.0284(15) 0.0336(16) -0.0006(13) 0.0200(15) -0.0055(15) N2 0.065(2) 0.0292(13) 0.0359(14) -0.0027(11) 0.0284(14) -0.0135(13) O2 0.085(2) 0.0430(13) 0.0364(12) -0.0059(10) 0.0350(12) -0.0083(12) C2 0.049(2) 0.0333(16) 0.0318(15) -0.0003(13) 0.0207(14) -0.0028(14) O3 0.0634(17) 0.0282(11) 0.0415(12) 0.0001(9) 0.0180(11) -0.0088(10) C3 0.043(2) 0.0250(14) 0.0289(14) -0.0025(11) 0.0190(14) -0.0045(13) O4 0.106(2) 0.0367(13) 0.0605(16) -0.0071(13) 0.0257(15) -0.0097(14) C4 0.039(3) 0.0289(15) 0.0404(18) -0.0016(13) 0.0189(16) -0.0006(15) O5 0.0724(19) 0.0310(12) 0.0573(15) 0.0051(11) 0.0225(13) -0.0004(11) C5 0.047(3) 0.0276(16) 0.0360(17) 0.0019(13) 0.0167(16) -0.0002(15) C6 0.053(3) 0.0317(16) 0.0422(18) -0.0008(14) 0.0262(17) -0.0058(15) C7 0.043(3) 0.0377(18) 0.053(2) -0.0044(16) 0.0261(18) -0.0011(16) C8 0.046(3) 0.0310(16) 0.0420(18) -0.0001(14) 0.0180(16) 0.0022(16) C9 0.036(2) 0.0321(16) 0.0469(19) 0.0039(14) 0.0169(15) -0.0040(14) C10 0.049(2) 0.0366(17) 0.0385(18) 0.0005(14) 0.0154(16) -0.0043(15) C11 0.048(2) 0.0382(17) 0.0458(19) -0.0044(15) 0.0201(17) -0.0046(16) C12 0.036(2) 0.0342(16) 0.0477(19) 0.0025(14) 0.0175(15) -0.0010(14) C13 0.058(3) 0.0381(18) 0.046(2) 0.0032(16) 0.0166(18) -0.0075(16) C14 0.062(3) 0.0343(17) 0.0426(19) -0.0040(15) 0.0130(18) -0.0131(16) C15 0.047(2) 0.0342(17) 0.053(2) 0.0008(16) 0.0168(17) -0.0013(16) C16 0.078(3) 0.0340(19) 0.073(3) 0.0148(17) 0.026(2) 0.0001(18) _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 N1 C1 1.352(4) . ? N1 C3 1.469(4) . ? O1 C1 1.236(3) . ? C1 N2 1.398(4) . ? N2 C2 1.371(4) . ? O2 C2 1.223(3) . ? C2 C3 1.527(4) . ? O3 C9 1.381(4) . ? O3 C6 1.467(4) . ? C3 C4 1.542(4) . ? C3 C8 1.543(5) . ? O4 C15 1.210(4) . ? C4 C5 1.533(4) . ? O5 C15 1.341(4) . ? O5 C16 1.447(4) . ? C5 C6 1.529(5) . ? C6 C7 1.526(5) . ? C7 C8 1.538(5) . ? C9 C10 1.395(4) . ? C9 C14 1.395(4) . ? C10 C11 1.396(4) . ? C11 C12 1.402(4) . ? C12 C13 1.384(5) . ? C12 C15 1.495(4) . ? C13 C14 1.397(4) . ? 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 N1 C3 112.5(2) . . ? O1 C1 N1 127.6(3) . . ? O1 C1 N2 125.0(3) . . ? N1 C1 N2 107.4(2) . . ? C2 N2 C1 111.7(2) . . ? O2 C2 N2 127.1(3) . . ? O2 C2 C3 125.7(3) . . ? N2 C2 C3 107.2(2) . . ? C9 O3 C6 118.4(2) . . ? N1 C3 C2 100.9(2) . . ? N1 C3 C4 112.1(2) . . ? C2 C3 C4 112.8(3) . . ? N1 C3 C8 111.8(2) . . ? C2 C3 C8 108.9(2) . . ? C4 C3 C8 110.0(2) . . ? C5 C4 C3 111.6(3) . . ? C15 O5 C16 117.9(3) . . ? C6 C5 C4 112.2(3) . . ? O3 C6 C7 106.9(3) . . ? O3 C6 C5 109.5(3) . . ? C7 C6 C5 112.6(3) . . ? C6 C7 C8 113.1(3) . . ? C7 C8 C3 111.2(3) . . ? O3 C9 C10 115.6(3) . . ? O3 C9 C14 124.3(3) . . ? C10 C9 C14 120.0(3) . . ? C9 C10 C11 119.9(3) . . ? C10 C11 C12 120.5(3) . . ? C13 C12 C11 118.7(3) . . ? C13 C12 C15 121.5(3) . . ? C11 C12 C15 119.8(3) . . ? C12 C13 C14 121.7(3) . . ? C9 C14 C13 119.1(3) . . ? O4 C15 O5 123.2(3) . . ? O4 C15 C12 125.6(3) . . ? O5 C15 C12 111.2(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 HN1 O2 0.85(4) 2.12(4) 2.963(3) 175(4) 6_556 N2 HN2 O1 0.88(4) 1.98(4) 2.839(3) 167(4) 7_556 O10 HO1 O4 0.98 2.02 2.979(4) 166.4 7_536 _diffrn_measured_fraction_theta_max 0.833 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.833 _refine_diff_density_max 0.303 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.046 # Attachment '- Compund4 revised.CIF' data_rx006 _database_code_depnum_ccdc_archive 'CCDC 855303' #TrackingRef '- Compund4 revised.CIF' _audit_creation_method 'CrysAlis RED' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 N2 O4' _chemical_formula_weight 332.39 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 6.047(2) _cell_length_b 6.272(3) _cell_length_c 26.102(8) _cell_angle_alpha 89.21(4) _cell_angle_beta 85.91(3) _cell_angle_gamma 66.67(4) _cell_volume 906.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.3990 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15453 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 23.23 _reflns_number_total 2525 _reflns_number_gt 1737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD Oxford Diffraction Ltd.Version 1.171.29.10' _computing_cell_refinement 'CrysAlis RED Oxford Diffraction Ltd.Version 1.171.29.10' _computing_data_reduction 'CrysAlis RED Oxford Diffraction Ltd.Version 1.171.29.10' _computing_structure_solution 'BRUKER SHELXTL' _computing_structure_refinement 'BRUKER SHELXTL' _computing_molecular_graphics 'BRUKER SHELXTL' _computing_publication_material 'BRUKER 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^)+(0.1271P)^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 2525 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1911 _refine_ls_wR_factor_gt 0.1783 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 O1 O -0.2795(3) 0.6487(3) 0.53921(8) 0.0479(6) Uani 1 1 d . . . C1 C -0.3811(5) 0.7029(5) 0.49808(13) 0.0397(7) Uani 1 1 d . . . N1 N -0.2706(5) 0.6574(4) 0.45078(10) 0.0464(7) Uani 1 1 d . . . HN1 H -0.109(6) 0.578(5) 0.4489(11) 0.046(8) Uiso 1 1 d . . . N2 N -0.6498(4) 0.8285(4) 0.49284(10) 0.0399(7) Uani 1 1 d . . . HN2 H -0.779(6) 0.891(5) 0.5168(12) 0.052(9) Uiso 1 1 d . . . O2 O -0.9310(3) 0.9717(3) 0.42719(8) 0.0506(6) Uani 1 1 d . . . C2 C -0.7119(5) 0.8648(4) 0.44257(12) 0.0392(7) Uani 1 1 d . . . O3 O 0.0753(4) 0.5057(4) 0.27934(10) 0.0710(8) Uani 1 1 d . . . C3 C -0.4570(5) 0.7455(5) 0.41003(11) 0.0395(8) Uani 1 1 d . . . C4 C -0.4320(6) 0.9177(6) 0.37316(14) 0.0482(9) Uani 1 1 d . . . H4B H -0.590(5) 1.009(5) 0.3520(11) 0.045(7) Uiso 1 1 d . . . H4A H -0.448(5) 1.025(6) 0.3918(12) 0.046(9) Uiso 1 1 d . . . C5 C -0.1842(6) 0.7997(6) 0.33952(14) 0.0532(9) Uani 1 1 d . . . H5B H -0.024(7) 0.729(6) 0.3593(13) 0.068(10) Uiso 1 1 d . . . H5A H -0.180(6) 0.923(6) 0.3129(13) 0.070(10) Uiso 1 1 d . . . C6 C -0.1663(6) 0.6082(5) 0.30958(13) 0.0490(8) Uani 1 1 d . . . H6 H -0.301(6) 0.680(5) 0.2888(12) 0.051(9) Uiso 1 1 d . . . C7 C -0.1814(6) 0.4324(6) 0.34540(14) 0.0521(9) Uani 1 1 d . . . H7B H -0.168(5) 0.303(6) 0.3248(12) 0.056(9) Uiso 1 1 d . . . H7A H -0.024(6) 0.354(5) 0.3638(11) 0.049(8) Uiso 1 1 d . . . C8 C -0.4327(6) 0.5498(6) 0.37848(14) 0.0488(9) Uani 1 1 d . . . H8A H -0.577(6) 0.619(5) 0.3559(12) 0.056(9) Uiso 1 1 d . . . H8B H -0.452(5) 0.440(5) 0.4002(11) 0.042(8) Uiso 1 1 d . . . C9 C 0.1307(6) 0.3359(6) 0.24538(14) 0.0615(10) Uani 1 1 d . . . C10 C -0.0499(9) 0.3135(8) 0.22166(18) 0.0855(14) Uani 1 1 d . . . H10 H -0.211(8) 0.416(7) 0.2279(17) 0.097(14) Uiso 1 1 d . . . C11 C 0.0281(10) 0.1321(9) 0.1881(2) 0.0974(16) Uani 1 1 d . . . H11 H -0.089(8) 0.122(8) 0.1687(18) 0.103(15) Uiso 1 1 d . . . C12 C 0.2898(9) -0.0261(7) 0.17830(18) 0.0871(14) Uani 1 1 d . . . C13 C 0.4693(9) 0.0011(8) 0.20081(19) 0.0829(13) Uani 1 1 d . . . H13 H 0.660(10) -0.117(9) 0.189(2) 0.142(18) Uiso 1 1 d . . . C14 C 0.3926(8) 0.1783(7) 0.23405(17) 0.0722(11) Uani 1 1 d . . . H14 H 0.508(7) 0.201(7) 0.2549(15) 0.085(13) Uiso 1 1 d . . . O4 O 0.3861(7) -0.2114(6) 0.14681(14) 0.1284(14) Uani 1 1 d G . . C15 C 0.2181(6) -0.2597(7) 0.1273(2) 0.149(3) Uani 1 1 d G . . C16 C 0.3740(8) -0.4907(6) 0.09633(15) 0.161(3) Uani 1 1 d G . . C18 C 0.3507(16) -0.7737(10) 0.0456(2) 0.276(7) Uani 1 1 d G . . C17 C 0.2001(11) -0.5421(9) 0.0750(2) 0.230(5) Uani 1 1 d G . . 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 0.0459(12) 0.0545(13) 0.0475(14) -0.0009(10) -0.0045(11) -0.0241(10) C1 0.0398(17) 0.0369(16) 0.047(2) -0.0059(14) 0.0029(17) -0.0208(13) N1 0.0321(16) 0.0546(16) 0.0514(19) -0.0038(13) 0.0005(14) -0.0165(12) N2 0.0323(15) 0.0415(14) 0.0476(18) -0.0062(12) 0.0045(13) -0.0175(11) O2 0.0380(13) 0.0564(13) 0.0592(15) -0.0043(10) -0.0047(10) -0.0202(10) C2 0.0364(17) 0.0345(15) 0.052(2) -0.0039(13) 0.0000(14) -0.0198(13) O3 0.0684(16) 0.0870(17) 0.0731(18) -0.0331(15) 0.0274(13) -0.0516(14) C3 0.0363(16) 0.0387(16) 0.0470(18) -0.0031(14) -0.0002(14) -0.0189(12) C4 0.055(2) 0.0399(18) 0.057(2) -0.0091(17) 0.0011(18) -0.0263(16) C5 0.063(2) 0.055(2) 0.055(2) -0.0075(17) 0.0073(18) -0.0391(17) C6 0.0450(19) 0.0536(19) 0.053(2) -0.0073(16) 0.0056(17) -0.0259(15) C7 0.055(2) 0.0426(18) 0.060(2) -0.0105(17) 0.0089(18) -0.0229(16) C8 0.056(2) 0.0421(18) 0.057(2) -0.0018(17) 0.0047(18) -0.0295(16) C9 0.067(2) 0.066(2) 0.058(2) -0.0109(19) 0.0135(19) -0.0358(19) C10 0.071(3) 0.091(3) 0.098(3) -0.039(3) 0.017(3) -0.039(3) C11 0.099(4) 0.109(4) 0.097(4) -0.047(3) 0.016(3) -0.058(3) C12 0.110(4) 0.075(3) 0.082(3) -0.030(2) 0.032(3) -0.048(3) C13 0.081(3) 0.071(3) 0.091(3) -0.012(2) 0.020(3) -0.028(2) C14 0.069(3) 0.077(3) 0.071(3) -0.010(2) 0.010(2) -0.032(2) O4 0.147(3) 0.115(3) 0.133(3) -0.067(2) 0.046(3) -0.069(2) C15 0.194(7) 0.148(5) 0.139(5) -0.074(4) 0.026(5) -0.107(5) C16 0.216(8) 0.136(5) 0.150(6) -0.073(5) 0.024(5) -0.093(5) C18 0.54(2) 0.158(7) 0.175(8) -0.051(6) -0.003(11) -0.191(11) C17 0.366(14) 0.177(7) 0.195(8) -0.065(7) -0.009(9) -0.158(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.251(3) . ? C1 N1 1.339(4) . ? C1 N2 1.515(4) . ? N1 C3 1.539(4) . ? N2 C2 1.382(4) . ? O2 C2 1.316(3) . ? C2 C3 1.604(4) . ? O3 C9 1.317(4) . ? O3 C6 1.509(4) . ? C3 C8 1.440(4) . ? C3 C4 1.482(4) . ? C4 C5 1.586(5) . ? C5 C6 1.406(4) . ? C6 C7 1.463(5) . ? C7 C8 1.594(5) . ? C9 C10 1.348(6) . ? C9 C14 1.509(5) . ? C10 C11 1.352(6) . ? C11 C12 1.504(7) . ? C12 O4 1.337(5) . ? C12 C13 1.339(6) . ? C13 C14 1.328(6) . ? O4 C15 1.3061 . ? C15 C16 1.5751 . ? C16 C17 1.3691 . ? C18 C17 1.5535 . ? 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 O1 C1 N1 125.8(3) . . ? O1 C1 N2 126.3(3) . . ? N1 C1 N2 108.0(3) . . ? C1 N1 C3 110.4(3) . . ? C2 N2 C1 113.9(3) . . ? O2 C2 N2 126.4(3) . . ? O2 C2 C3 130.4(3) . . ? N2 C2 C3 103.2(2) . . ? C9 O3 C6 122.9(2) . . ? C8 C3 C4 104.6(3) . . ? C8 C3 N1 107.8(2) . . ? C4 C3 N1 117.2(2) . . ? C8 C3 C2 115.0(2) . . ? C4 C3 C2 108.1(2) . . ? N1 C3 C2 104.6(2) . . ? C3 C4 C5 108.7(3) . . ? C6 C5 C4 114.5(3) . . ? C5 C6 C7 106.7(3) . . ? C5 C6 O3 110.9(3) . . ? C7 C6 O3 107.7(3) . . ? C6 C7 C8 106.5(3) . . ? C3 C8 C7 115.3(3) . . ? O3 C9 C10 118.3(3) . . ? O3 C9 C14 118.7(3) . . ? C10 C9 C14 123.0(4) . . ? C9 C10 C11 113.0(5) . . ? C10 C11 C12 123.1(5) . . ? O4 C12 C13 108.2(4) . . ? O4 C12 C11 128.1(5) . . ? C13 C12 C11 123.7(4) . . ? C14 C13 C12 113.2(4) . . ? C13 C14 C9 124.0(4) . . ? C15 O4 C12 111.1(3) . . ? O4 C15 C16 101.2 . . ? C17 C16 C15 101.9 . . ? C16 C17 C18 102.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 HN1 O1 0.90(3) 2.26(3) 3.142(4) 168(3) 2_566 N2 HN2 O2 0.92(3) 2.10(4) 3.025(4) 179(3) 2_376 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 23.23 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.366 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.050