# Electronic Supplementary Material (ESI) for RSC Advances # 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_phphs _database_code_depnum_ccdc_archive 'CCDC 890285' #TrackingRef 'phphs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C15 H11 N3 S' _chemical_formula_sum 'C15 H11 N3 S' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _diffrn_ambient_temperature 110(2) _chemical_formula_weight 265.33 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _chemical_absolute_configuration unk loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.9527(3) _cell_length_b 10.0187(5) _cell_length_c 20.8776(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1245.10(11) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2237 _cell_measurement_theta_min 2.8123 _cell_measurement_theta_max 29.1187 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98875 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6204 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 29.18 _reflns_number_total 2869 _reflns_number_gt 2614 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0384P)^2^+0.1825P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.09(8) _refine_ls_number_reflns 2869 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0834 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 S S 0.25058(8) 0.56286(5) 0.99533(2) 0.02076(12) Uani 1 1 d . . . N1 N -0.1680(3) 0.52717(15) 1.16283(7) 0.0177(3) Uani 1 1 d . . . N2 N -0.3261(3) 0.62137(17) 1.14981(8) 0.0228(4) Uani 1 1 d . . . N3 N -0.3028(3) 0.65516(16) 1.08933(8) 0.0224(4) Uani 1 1 d . . . C1 C 0.2844(3) 0.42677(17) 1.04879(8) 0.0168(4) Uani 1 1 d . . . C2 C 0.4682(3) 0.34323(19) 1.03973(9) 0.0202(4) Uani 1 1 d . . . H2B H 0.5656 0.3574 1.0043 0.024 Uiso 1 1 calc R . . C3 C 0.5105(3) 0.23939(19) 1.08200(9) 0.0224(4) Uani 1 1 d . . . H3B H 0.6405 0.1855 1.0767 0.027 Uiso 1 1 calc R . . C4 C 0.3626(3) 0.21432(19) 1.13204(9) 0.0202(4) Uani 1 1 d . . . H4A H 0.3885 0.1410 1.1599 0.024 Uiso 1 1 calc R . . C5 C 0.1782(3) 0.29565(19) 1.14144(9) 0.0192(4) Uani 1 1 d . . . H5A H 0.0762 0.2767 1.1753 0.023 Uiso 1 1 calc R . . C6 C 0.1400(3) 0.40595(17) 1.10147(8) 0.0156(4) Uani 1 1 d . . . C7 C -0.0434(3) 0.50031(18) 1.10973(8) 0.0168(4) Uani 1 1 d . . . C8 C -0.1320(3) 0.58276(19) 1.06364(8) 0.0184(4) Uani 1 1 d . . . C9 C -0.0519(3) 0.58750(18) 0.99603(9) 0.0206(4) Uani 1 1 d . . . H9A H -0.0896 0.6749 0.9767 0.025 Uiso 1 1 calc R . . H9B H -0.1263 0.5167 0.9706 0.025 Uiso 1 1 calc R . . C10 C -0.1432(3) 0.47880(18) 1.22706(8) 0.0167(4) Uani 1 1 d . . . C11 C 0.0553(3) 0.5065(2) 1.25987(9) 0.0196(4) Uani 1 1 d . . . H11A H 0.1693 0.5596 1.2408 0.024 Uiso 1 1 calc R . . C12 C 0.0828(3) 0.4549(2) 1.32097(9) 0.0231(4) Uani 1 1 d . . . H12A H 0.2171 0.4725 1.3440 0.028 Uiso 1 1 calc R . . C13 C -0.0839(3) 0.3779(2) 1.34859(9) 0.0227(4) Uani 1 1 d . . . H13A H -0.0630 0.3424 1.3904 0.027 Uiso 1 1 calc R . . C14 C -0.2803(3) 0.3523(2) 1.31576(9) 0.0234(4) Uani 1 1 d . . . H14A H -0.3950 0.3003 1.3352 0.028 Uiso 1 1 calc R . . C15 C -0.3109(3) 0.40270(19) 1.25418(9) 0.0211(4) Uani 1 1 d . . . H15A H -0.4454 0.3848 1.2312 0.025 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 S 0.0248(2) 0.0189(2) 0.0185(2) 0.00457(18) 0.0006(2) -0.0043(2) N1 0.0184(7) 0.0171(8) 0.0177(7) 0.0004(6) 0.0002(6) 0.0040(7) N2 0.0214(8) 0.0243(9) 0.0226(8) -0.0003(7) -0.0027(7) 0.0052(8) N3 0.0233(8) 0.0197(8) 0.0242(8) 0.0006(7) -0.0050(7) 0.0024(7) C1 0.0211(9) 0.0142(8) 0.0153(8) -0.0012(7) -0.0017(7) -0.0049(8) C2 0.0204(9) 0.0200(9) 0.0201(10) -0.0044(8) 0.0038(7) -0.0037(8) C3 0.0226(9) 0.0199(10) 0.0248(10) -0.0056(8) 0.0008(8) 0.0018(9) C4 0.0274(10) 0.0145(9) 0.0186(9) 0.0001(8) -0.0015(8) 0.0035(8) C5 0.0238(9) 0.0166(9) 0.0173(9) 0.0004(7) 0.0021(7) -0.0009(8) C6 0.0181(8) 0.0139(9) 0.0146(8) -0.0026(7) -0.0017(7) -0.0021(7) C7 0.0198(9) 0.0159(8) 0.0147(8) -0.0021(7) -0.0015(7) -0.0036(8) C8 0.0203(8) 0.0158(9) 0.0189(9) 0.0009(7) -0.0037(7) -0.0021(8) C9 0.0250(9) 0.0174(9) 0.0194(9) 0.0008(8) -0.0051(8) -0.0011(8) C10 0.0191(9) 0.0167(9) 0.0145(8) -0.0026(7) 0.0001(7) 0.0042(8) C11 0.0166(9) 0.0229(10) 0.0194(9) -0.0006(8) 0.0017(7) -0.0004(8) C12 0.0192(9) 0.0291(11) 0.0210(9) -0.0013(9) -0.0017(7) 0.0013(9) C13 0.0275(10) 0.0222(10) 0.0183(9) 0.0010(8) 0.0020(8) 0.0038(9) C14 0.0242(10) 0.0205(9) 0.0253(10) 0.0007(8) 0.0080(8) -0.0043(9) C15 0.0167(8) 0.0234(10) 0.0232(9) -0.0044(8) -0.0002(7) -0.0012(8) _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 S C1 1.7735(18) . ? S C9 1.8176(19) . ? N1 N2 1.360(2) . ? N1 C7 1.360(2) . ? N1 C10 1.433(2) . ? N2 N3 1.315(2) . ? N3 C8 1.359(2) . ? C1 C2 1.390(3) . ? C1 C6 1.411(2) . ? C2 C3 1.387(3) . ? C2 H2B 0.9500 . ? C3 C4 1.389(3) . ? C3 H3B 0.9500 . ? C4 C5 1.381(3) . ? C4 H4A 0.9500 . ? C5 C6 1.403(2) . ? C5 H5A 0.9500 . ? C6 C7 1.454(2) . ? C7 C8 1.374(3) . ? C8 C9 1.491(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C15 1.378(3) . ? C10 C11 1.394(3) . ? C11 C12 1.386(3) . ? C11 H11A 0.9500 . ? C12 C13 1.382(3) . ? C12 H12A 0.9500 . ? C13 C14 1.380(3) . ? C13 H13A 0.9500 . ? C14 C15 1.393(3) . ? C14 H14A 0.9500 . ? C15 H15A 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 C1 S C9 102.24(8) . . ? N2 N1 C7 110.58(14) . . ? N2 N1 C10 119.52(14) . . ? C7 N1 C10 129.73(15) . . ? N3 N2 N1 107.32(15) . . ? N2 N3 C8 108.69(15) . . ? C2 C1 C6 119.76(17) . . ? C2 C1 S 117.81(13) . . ? C6 C1 S 122.33(13) . . ? C1 C2 C3 120.50(17) . . ? C1 C2 H2B 119.7 . . ? C3 C2 H2B 119.7 . . ? C2 C3 C4 119.95(18) . . ? C2 C3 H3B 120.0 . . ? C4 C3 H3B 120.0 . . ? C5 C4 C3 120.26(17) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? C4 C5 C6 120.58(17) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C5 C6 C1 118.76(16) . . ? C5 C6 C7 124.25(16) . . ? C1 C6 C7 116.97(15) . . ? N1 C7 C8 104.04(16) . . ? N1 C7 C6 129.37(16) . . ? C8 C7 C6 126.59(16) . . ? N3 C8 C7 109.38(16) . . ? N3 C8 C9 126.58(16) . . ? C7 C8 C9 124.03(17) . . ? C8 C9 S 108.67(12) . . ? C8 C9 H9A 110.0 . . ? S C9 H9A 110.0 . . ? C8 C9 H9B 110.0 . . ? S C9 H9B 110.0 . . ? H9A C9 H9B 108.3 . . ? C15 C10 C11 121.51(17) . . ? C15 C10 N1 119.79(16) . . ? C11 C10 N1 118.67(17) . . ? C12 C11 C10 118.54(18) . . ? C12 C11 H11A 120.7 . . ? C10 C11 H11A 120.7 . . ? C13 C12 C11 120.50(18) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C14 C13 C12 120.31(18) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C15 120.13(18) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? C10 C15 C14 119.01(17) . . ? C10 C15 H15A 120.5 . . ? C14 C15 H15A 120.5 . . ? _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.306 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.049 data_tmaphn _database_code_depnum_ccdc_archive 'CCDC 890286' #TrackingRef 'tmaphn.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C18 H16 N4 O3' _chemical_formula_sum 'C18 H16 N4 O3' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour red _diffrn_ambient_temperature 110(2) _chemical_formula_weight 336.35 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 9.5689(5) _cell_length_b 14.0410(7) _cell_length_c 11.5099(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.885(5) _cell_angle_gamma 90.00 _cell_volume 1545.60(14) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1739 _cell_measurement_theta_min 2.7190 _cell_measurement_theta_max 29.1263 _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91079 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6758 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 29.19 _reflns_number_total 3564 _reflns_number_gt 2670 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0583P)^2^+0.5275P] 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 3564 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 0.98883(13) 0.35727(10) 0.21686(11) 0.0264(3) Uani 1 1 d . . . O2 O 0.97420(12) 0.22303(9) 0.05131(10) 0.0214(3) Uani 1 1 d . . . O3 O 0.79129(13) 0.07979(9) 0.05925(10) 0.0215(3) Uani 1 1 d . . . N1 N 0.51732(15) 0.04483(11) 0.70774(12) 0.0219(3) Uani 1 1 d . . . N2 N 0.45602(15) 0.26133(11) 0.53288(13) 0.0230(3) Uani 1 1 d . . . N3 N 0.52356(16) 0.27842(11) 0.43874(13) 0.0231(3) Uani 1 1 d . . . N4 N 0.61584(15) 0.20461(11) 0.42207(12) 0.0200(3) Uani 1 1 d . . . C1 C 0.62329(18) 0.00828(13) 0.64133(14) 0.0196(4) Uani 1 1 d . . . C2 C 0.68236(19) -0.07903(13) 0.67774(15) 0.0224(4) Uani 1 1 d . . . H2B H 0.6470 -0.1105 0.7437 0.027 Uiso 1 1 calc R . . C3 C 0.7902(2) -0.11929(14) 0.61932(15) 0.0252(4) Uani 1 1 d . . . H3B H 0.8289 -0.1782 0.6452 0.030 Uiso 1 1 calc R . . C4 C 0.84369(19) -0.07416(14) 0.52188(16) 0.0245(4) Uani 1 1 d . . . H4A H 0.9192 -0.1022 0.4826 0.029 Uiso 1 1 calc R . . C5 C 0.78743(18) 0.01050(14) 0.48282(15) 0.0223(4) Uani 1 1 d . . . H5A H 0.8243 0.0407 0.4166 0.027 Uiso 1 1 calc R . . C6 C 0.67556(18) 0.05267(13) 0.54026(15) 0.0192(4) Uani 1 1 d . . . C7 C 0.60623(17) 0.13968(13) 0.50906(14) 0.0186(4) Uani 1 1 d . . . C8 C 0.50278(18) 0.17634(13) 0.57820(15) 0.0202(4) Uani 1 1 d . . . C9 C 0.46074(18) 0.12641(13) 0.67779(15) 0.0216(4) Uani 1 1 d . . . H9A H 0.3899 0.1527 0.7240 0.026 Uiso 1 1 calc R . . C10 C 0.70628(18) 0.20920(13) 0.32457(14) 0.0188(4) Uani 1 1 d . . . C11 C 0.79867(18) 0.28457(13) 0.32059(15) 0.0198(4) Uani 1 1 d . . . H11A H 0.8001 0.3326 0.3788 0.024 Uiso 1 1 calc R . . C12 C 0.88945(18) 0.28821(13) 0.22907(15) 0.0199(4) Uani 1 1 d . . . C13 C 0.88599(18) 0.21784(13) 0.14362(14) 0.0194(4) Uani 1 1 d . . . C14 C 0.78833(17) 0.14402(12) 0.14839(14) 0.0179(4) Uani 1 1 d . . . C15 C 0.69705(18) 0.13894(13) 0.23996(14) 0.0197(4) Uani 1 1 d . . . H15A H 0.6306 0.0889 0.2443 0.024 Uiso 1 1 calc R . . C16 C 0.9864(2) 0.43576(14) 0.29558(16) 0.0277(4) Uani 1 1 d . . . H16A H 1.0620 0.4801 0.2782 0.042 Uiso 1 1 calc R . . H16B H 0.9992 0.4124 0.3755 0.042 Uiso 1 1 calc R . . H16C H 0.8963 0.4687 0.2871 0.042 Uiso 1 1 calc R . . C17 C 1.11326(19) 0.19036(15) 0.07921(17) 0.0285(4) Uani 1 1 d . . . H17A H 1.1706 0.1960 0.0105 0.043 Uiso 1 1 calc R . . H17B H 1.1101 0.1236 0.1037 0.043 Uiso 1 1 calc R . . H17C H 1.1541 0.2291 0.1424 0.043 Uiso 1 1 calc R . . C18 C 0.6779(2) 0.01317(14) 0.05081(17) 0.0270(4) Uani 1 1 d . . . H18A H 0.6907 -0.0290 -0.0159 0.040 Uiso 1 1 calc R . . H18B H 0.5894 0.0478 0.0404 0.040 Uiso 1 1 calc R . . H18C H 0.6761 -0.0249 0.1221 0.040 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 0.0298(7) 0.0238(7) 0.0260(7) -0.0042(6) 0.0056(5) -0.0113(6) O2 0.0207(6) 0.0247(7) 0.0189(6) 0.0014(5) 0.0026(5) -0.0021(5) O3 0.0247(6) 0.0182(7) 0.0217(6) -0.0029(5) 0.0019(5) -0.0038(5) N1 0.0232(7) 0.0220(8) 0.0207(7) -0.0001(7) 0.0026(6) -0.0032(6) N2 0.0220(8) 0.0215(8) 0.0256(8) -0.0004(7) 0.0042(6) 0.0001(6) N3 0.0229(8) 0.0204(8) 0.0262(8) 0.0002(7) 0.0031(6) 0.0021(6) N4 0.0213(7) 0.0173(8) 0.0213(7) 0.0004(6) 0.0021(6) 0.0007(6) C1 0.0208(8) 0.0190(9) 0.0189(8) -0.0019(7) -0.0001(7) -0.0046(7) C2 0.0263(9) 0.0209(9) 0.0199(8) 0.0022(8) -0.0017(7) -0.0034(8) C3 0.0296(10) 0.0209(10) 0.0248(9) -0.0020(8) -0.0040(7) 0.0014(8) C4 0.0241(9) 0.0241(10) 0.0252(9) -0.0046(8) -0.0002(7) 0.0029(8) C5 0.0237(9) 0.0238(10) 0.0196(8) -0.0009(8) 0.0020(7) 0.0006(8) C6 0.0189(8) 0.0180(9) 0.0206(8) -0.0024(7) -0.0016(7) -0.0025(7) C7 0.0190(8) 0.0185(9) 0.0182(8) -0.0009(7) 0.0008(6) -0.0039(7) C8 0.0196(8) 0.0201(9) 0.0210(9) -0.0018(7) 0.0009(7) -0.0015(7) C9 0.0203(8) 0.0235(10) 0.0213(9) -0.0035(8) 0.0040(7) -0.0026(7) C10 0.0191(8) 0.0193(9) 0.0181(8) 0.0027(7) 0.0021(7) 0.0006(7) C11 0.0231(9) 0.0177(9) 0.0186(8) -0.0008(7) 0.0002(7) -0.0004(7) C12 0.0199(8) 0.0180(9) 0.0216(9) 0.0031(7) -0.0018(7) -0.0034(7) C13 0.0202(8) 0.0202(9) 0.0179(8) 0.0029(7) -0.0004(6) -0.0003(7) C14 0.0193(8) 0.0155(8) 0.0188(8) 0.0006(7) -0.0026(6) 0.0008(7) C15 0.0196(8) 0.0180(9) 0.0213(9) 0.0022(7) -0.0010(7) -0.0015(7) C16 0.0344(10) 0.0208(10) 0.0279(10) -0.0033(8) 0.0007(8) -0.0083(8) C17 0.0238(9) 0.0300(11) 0.0320(10) 0.0049(9) 0.0056(8) 0.0036(8) C18 0.0275(9) 0.0230(10) 0.0306(10) -0.0078(8) 0.0036(8) -0.0069(8) _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 C12 1.369(2) . ? O1 C16 1.427(2) . ? O2 C13 1.380(2) . ? O2 C17 1.434(2) . ? O3 C14 1.367(2) . ? O3 C18 1.433(2) . ? N1 C9 1.308(2) . ? N1 C1 1.388(2) . ? N2 N3 1.302(2) . ? N2 C8 1.371(2) . ? N3 N4 1.379(2) . ? N4 C7 1.360(2) . ? N4 C10 1.441(2) . ? C1 C2 1.408(3) . ? C1 C6 1.425(2) . ? C2 C3 1.372(3) . ? C2 H2B 0.9500 . ? C3 C4 1.400(3) . ? C3 H3B 0.9500 . ? C4 C5 1.374(3) . ? C4 H4A 0.9500 . ? C5 C6 1.407(2) . ? C5 H5A 0.9500 . ? C6 C7 1.430(2) . ? C7 C8 1.389(2) . ? C8 C9 1.413(2) . ? C9 H9A 0.9500 . ? C10 C15 1.387(2) . ? C10 C11 1.381(2) . ? C11 C12 1.388(2) . ? C11 H11A 0.9500 . ? C12 C13 1.394(3) . ? C13 C14 1.398(2) . ? C14 C15 1.393(2) . ? C15 H15A 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 C12 O1 C16 117.12(14) . . ? C13 O2 C17 113.40(13) . . ? C14 O3 C18 116.55(13) . . ? C9 N1 C1 118.83(16) . . ? N3 N2 C8 108.19(15) . . ? N2 N3 N4 108.35(14) . . ? C7 N4 N3 110.03(14) . . ? C7 N4 C10 131.33(15) . . ? N3 N4 C10 118.58(14) . . ? N1 C1 C2 116.84(16) . . ? N1 C1 C6 124.76(17) . . ? C2 C1 C6 118.40(16) . . ? C3 C2 C1 120.93(17) . . ? C3 C2 H2B 119.5 . . ? C1 C2 H2B 119.5 . . ? C2 C3 C4 120.45(18) . . ? C2 C3 H3B 119.8 . . ? C4 C3 H3B 119.8 . . ? C5 C4 C3 120.27(18) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? C4 C5 C6 120.40(18) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C5 C6 C1 119.50(17) . . ? C5 C6 C7 126.52(17) . . ? C1 C6 C7 113.97(16) . . ? N4 C7 C8 103.89(16) . . ? N4 C7 C6 135.70(16) . . ? C8 C7 C6 120.40(16) . . ? N2 C8 C7 109.53(16) . . ? N2 C8 C9 129.95(17) . . ? C7 C8 C9 120.52(17) . . ? N1 C9 C8 121.44(17) . . ? N1 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C15 C10 C11 123.23(16) . . ? C15 C10 N4 119.28(15) . . ? C11 C10 N4 117.50(15) . . ? C12 C11 C10 118.08(16) . . ? C12 C11 H11A 121.0 . . ? C10 C11 H11A 121.0 . . ? O1 C12 C11 123.93(16) . . ? O1 C12 C13 115.49(15) . . ? C11 C12 C13 120.56(16) . . ? O2 C13 C14 119.73(15) . . ? O2 C13 C12 120.31(16) . . ? C14 C13 C12 119.89(16) . . ? O3 C14 C15 124.28(16) . . ? O3 C14 C13 115.42(15) . . ? C15 C14 C13 120.29(16) . . ? C10 C15 C14 117.90(16) . . ? C10 C15 H15A 121.1 . . ? C14 C15 H15A 121.1 . . ? O1 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 H17A 109.5 . . ? O2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C8 N2 N3 N4 -0.28(19) . . . . ? N2 N3 N4 C7 -0.42(19) . . . . ? N2 N3 N4 C10 -177.99(14) . . . . ? C9 N1 C1 C2 179.16(16) . . . . ? C9 N1 C1 C6 -0.8(3) . . . . ? N1 C1 C2 C3 -178.22(16) . . . . ? C6 C1 C2 C3 1.7(3) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C4 C5 C6 C1 1.7(3) . . . . ? C4 C5 C6 C7 -179.48(17) . . . . ? N1 C1 C6 C5 177.43(16) . . . . ? C2 C1 C6 C5 -2.5(2) . . . . ? N1 C1 C6 C7 -1.5(2) . . . . ? C2 C1 C6 C7 178.51(15) . . . . ? N3 N4 C7 C8 0.91(18) . . . . ? C10 N4 C7 C8 178.07(17) . . . . ? N3 N4 C7 C6 -177.75(19) . . . . ? C10 N4 C7 C6 -0.6(3) . . . . ? C5 C6 C7 N4 2.7(3) . . . . ? C1 C6 C7 N4 -178.44(18) . . . . ? C5 C6 C7 C8 -175.81(17) . . . . ? C1 C6 C7 C8 3.1(2) . . . . ? N3 N2 C8 C7 0.9(2) . . . . ? N3 N2 C8 C9 -178.79(17) . . . . ? N4 C7 C8 N2 -1.08(19) . . . . ? C6 C7 C8 N2 177.84(15) . . . . ? N4 C7 C8 C9 178.62(15) . . . . ? C6 C7 C8 C9 -2.5(3) . . . . ? C1 N1 C9 C8 1.6(3) . . . . ? N2 C8 C9 N1 179.59(17) . . . . ? C7 C8 C9 N1 0.0(3) . . . . ? C7 N4 C10 C15 64.0(2) . . . . ? N3 N4 C10 C15 -119.05(18) . . . . ? C7 N4 C10 C11 -116.0(2) . . . . ? N3 N4 C10 C11 60.9(2) . . . . ? C15 C10 C11 C12 -2.0(3) . . . . ? N4 C10 C11 C12 177.99(15) . . . . ? C16 O1 C12 C11 -7.9(2) . . . . ? C16 O1 C12 C13 173.72(15) . . . . ? C10 C11 C12 O1 -177.90(16) . . . . ? C10 C11 C12 C13 0.4(3) . . . . ? C17 O2 C13 C14 -102.58(19) . . . . ? C17 O2 C13 C12 80.4(2) . . . . ? O1 C12 C13 O2 -3.1(2) . . . . ? C11 C12 C13 O2 178.45(15) . . . . ? O1 C12 C13 C14 179.91(15) . . . . ? C11 C12 C13 C14 1.4(3) . . . . ? C18 O3 C14 C15 10.8(2) . . . . ? C18 O3 C14 C13 -169.67(15) . . . . ? O2 C13 C14 O3 1.6(2) . . . . ? C12 C13 C14 O3 178.59(15) . . . . ? O2 C13 C14 C15 -178.84(15) . . . . ? C12 C13 C14 C15 -1.8(3) . . . . ? C11 C10 C15 C14 1.7(3) . . . . ? N4 C10 C15 C14 -178.37(15) . . . . ? O3 C14 C15 C10 179.86(15) . . . . ? C13 C14 C15 C10 0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.852 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.308 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.054 data_tmapho _database_code_depnum_ccdc_archive 'CCDC 890287' #TrackingRef 'tmapho.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C18 H17 N3 O4' _chemical_formula_sum 'C18 H17 N3 O4' _chemical_melting_point ? _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _diffrn_ambient_temperature 297(2) _chemical_formula_weight 339.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 9.7873(2) _cell_length_b 13.8510(3) _cell_length_c 11.8661(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.573(2) _cell_angle_gamma 90.00 _cell_volume 1608.53(6) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4450 _cell_measurement_theta_min 3.1880 _cell_measurement_theta_max 71.4744 _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.68 _exptl_crystal_size_min 0.58 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.837 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.78851 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6441 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.52 _diffrn_reflns_theta_max 71.61 _reflns_number_total 3056 _reflns_number_gt 2535 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0641P)^2^+0.2197P] 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 SHELXL _refine_ls_extinction_coef 0.0084(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3056 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1145 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.99487(14) 0.04353(10) 0.69337(12) 0.0743(4) Uani 1 1 d . . . O2 O 0.71318(10) 0.08012(8) 0.06791(8) 0.0453(3) Uani 1 1 d . . . O3 O 0.52641(10) 0.21993(8) 0.05563(8) 0.0478(3) Uani 1 1 d . . . O4 O 0.50412(12) 0.35330(9) 0.21713(10) 0.0619(4) Uani 1 1 d . . . N1 N 1.04243(14) 0.26737(10) 0.53015(11) 0.0525(4) Uani 1 1 d . . . N2 N 0.97002(15) 0.28416(10) 0.43821(12) 0.0536(4) Uani 1 1 d . . . N3 N 0.87990(12) 0.20995(9) 0.42554(10) 0.0424(3) Uani 1 1 d . . . C1 C 0.99936(14) 0.18350(11) 0.57479(12) 0.0414(3) Uani 1 1 d . . . C2 C 1.05225(17) 0.13570(13) 0.67809(13) 0.0508(4) Uani 1 1 d . . . H2B H 1.1508 0.1298 0.6733 0.061 Uiso 1 1 calc R . . H2C H 1.0318 0.1756 0.7430 0.061 Uiso 1 1 calc R . . C3 C 0.88203(15) 0.01072(12) 0.63724(13) 0.0452(4) Uani 1 1 d . . . C4 C 0.82644(18) -0.07469(13) 0.67524(15) 0.0566(4) Uani 1 1 d . . . H4A H 0.8639 -0.1053 0.7381 0.068 Uiso 1 1 calc R . . C5 C 0.71561(19) -0.11470(14) 0.62028(15) 0.0602(5) Uani 1 1 d . . . H5A H 0.6795 -0.1728 0.6456 0.072 Uiso 1 1 calc R . . C6 C 0.65776(19) -0.06936(14) 0.52807(15) 0.0606(5) Uani 1 1 d . . . H6A H 0.5824 -0.0965 0.4917 0.073 Uiso 1 1 calc R . . C7 C 0.71224(17) 0.01650(13) 0.48999(13) 0.0532(4) Uani 1 1 d . . . H7A H 0.6721 0.0474 0.4285 0.064 Uiso 1 1 calc R . . C8 C 0.82620(14) 0.05745(11) 0.54213(11) 0.0398(3) Uani 1 1 d . . . C9 C 0.89574(14) 0.14570(10) 0.51104(11) 0.0377(3) Uani 1 1 d . . . C10 C 0.78818(14) 0.21107(10) 0.32967(11) 0.0393(3) Uani 1 1 d . . . C11 C 0.80074(14) 0.14120(10) 0.24719(11) 0.0392(3) Uani 1 1 d . . . H11A H 0.8671 0.0934 0.2531 0.047 Uiso 1 1 calc R . . C12 C 0.71170(14) 0.14424(10) 0.15522(11) 0.0361(3) Uani 1 1 d . . . C13 C 0.61197(14) 0.21583(10) 0.14796(11) 0.0384(3) Uani 1 1 d . . . C14 C 0.60416(15) 0.28615(11) 0.23196(12) 0.0422(3) Uani 1 1 d . . . C15 C 0.69307(15) 0.28395(11) 0.32385(12) 0.0436(4) Uani 1 1 d . . . H15A H 0.6884 0.3306 0.3800 0.052 Uiso 1 1 calc R . . C16 C 0.82424(17) 0.01393(13) 0.06312(15) 0.0559(4) Uani 1 1 d . . . H16A H 0.8135 -0.0268 -0.0018 0.084 Uiso 1 1 calc R . . H16B H 0.8255 -0.0251 0.1300 0.084 Uiso 1 1 calc R . . H16C H 0.9085 0.0490 0.0580 0.084 Uiso 1 1 calc R . . C17 C 0.39346(18) 0.18296(17) 0.07400(17) 0.0702(6) Uani 1 1 d . . . H17A H 0.3403 0.1883 0.0059 0.105 Uiso 1 1 calc R . . H17B H 0.3504 0.2192 0.1328 0.105 Uiso 1 1 calc R . . H17C H 0.3996 0.1163 0.0958 0.105 Uiso 1 1 calc R . . C18 C 0.5072(2) 0.43554(14) 0.28770(17) 0.0693(5) Uani 1 1 d . . . H18A H 0.4316 0.4769 0.2692 0.104 Uiso 1 1 calc R . . H18B H 0.5913 0.4699 0.2769 0.104 Uiso 1 1 calc R . . H18C H 0.5009 0.4156 0.3650 0.104 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 0.0742(8) 0.0706(8) 0.0773(9) 0.0256(7) -0.0435(7) -0.0098(7) O2 0.0506(6) 0.0483(6) 0.0368(5) -0.0074(4) -0.0078(4) 0.0094(5) O3 0.0453(6) 0.0637(7) 0.0341(5) 0.0025(5) -0.0096(4) 0.0094(5) O4 0.0645(7) 0.0628(7) 0.0581(7) -0.0130(6) -0.0165(6) 0.0305(6) N1 0.0529(8) 0.0566(8) 0.0475(7) -0.0013(6) -0.0153(6) -0.0037(6) N2 0.0579(8) 0.0525(8) 0.0502(8) 0.0039(6) -0.0158(6) -0.0076(6) N3 0.0451(7) 0.0459(7) 0.0361(6) 0.0005(5) -0.0096(5) 0.0006(5) C1 0.0399(7) 0.0491(8) 0.0350(7) -0.0060(6) -0.0069(5) 0.0056(6) C2 0.0512(9) 0.0625(10) 0.0385(8) -0.0025(7) -0.0128(6) 0.0032(7) C3 0.0441(8) 0.0507(9) 0.0407(7) -0.0014(7) -0.0040(6) 0.0087(7) C4 0.0631(10) 0.0568(10) 0.0500(9) 0.0097(8) -0.0014(8) 0.0066(8) C5 0.0692(11) 0.0558(10) 0.0559(10) 0.0021(8) 0.0079(8) -0.0075(9) C6 0.0614(11) 0.0685(11) 0.0518(10) -0.0043(8) -0.0034(8) -0.0166(9) C7 0.0551(9) 0.0651(11) 0.0391(8) 0.0027(7) -0.0082(7) -0.0085(8) C8 0.0407(7) 0.0465(8) 0.0323(7) -0.0042(6) -0.0013(5) 0.0053(6) C9 0.0384(7) 0.0452(8) 0.0295(6) -0.0037(6) -0.0051(5) 0.0072(6) C10 0.0408(7) 0.0455(8) 0.0316(6) 0.0032(6) -0.0067(5) 0.0009(6) C11 0.0401(7) 0.0409(7) 0.0365(7) 0.0026(6) -0.0054(5) 0.0066(6) C12 0.0389(7) 0.0393(7) 0.0300(6) 0.0022(5) -0.0006(5) 0.0004(6) C13 0.0385(7) 0.0474(8) 0.0292(6) 0.0046(6) -0.0032(5) 0.0042(6) C14 0.0428(8) 0.0471(8) 0.0366(7) 0.0026(6) -0.0025(6) 0.0102(6) C15 0.0492(8) 0.0476(8) 0.0338(7) -0.0040(6) -0.0041(6) 0.0068(6) C16 0.0568(10) 0.0522(9) 0.0585(10) -0.0141(8) -0.0068(8) 0.0130(8) C17 0.0564(11) 0.0837(14) 0.0701(12) 0.0112(11) -0.0227(9) -0.0132(10) C18 0.0850(13) 0.0579(11) 0.0650(12) -0.0093(9) -0.0044(10) 0.0292(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 C3 1.3620(19) . ? O1 C2 1.407(2) . ? O2 C12 1.3649(16) . ? O2 C16 1.4235(18) . ? O3 C13 1.3735(16) . ? O3 C17 1.417(2) . ? O4 C14 1.3606(17) . ? O4 C18 1.414(2) . ? N1 N2 1.3157(18) . ? N1 C1 1.346(2) . ? N2 N3 1.3618(18) . ? N3 C9 1.3573(18) . ? N3 C10 1.4421(17) . ? C1 C9 1.3637(19) . ? C1 C2 1.482(2) . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? C3 C4 1.380(2) . ? C3 C8 1.407(2) . ? C4 C5 1.377(3) . ? C4 H4A 0.9300 . ? C5 C6 1.378(3) . ? C5 H5A 0.9300 . ? C6 C7 1.381(2) . ? C6 H6A 0.9300 . ? C7 C8 1.391(2) . ? C7 H7A 0.9300 . ? C8 C9 1.449(2) . ? C10 C15 1.374(2) . ? C10 C11 1.383(2) . ? C11 C12 1.3904(18) . ? C11 H11A 0.9300 . ? C12 C13 1.3934(19) . ? C13 C14 1.396(2) . ? C14 C15 1.389(2) . ? C15 H15A 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C3 O1 C2 124.22(12) . . ? C12 O2 C16 117.60(11) . . ? C13 O3 C17 114.56(12) . . ? C14 O4 C18 117.57(13) . . ? N2 N1 C1 108.10(12) . . ? N1 N2 N3 107.52(12) . . ? N2 N3 C9 110.08(11) . . ? N2 N3 C10 118.45(12) . . ? C9 N3 C10 131.47(12) . . ? N1 C1 C9 110.31(13) . . ? N1 C1 C2 127.08(14) . . ? C9 C1 C2 122.61(15) . . ? O1 C2 C1 112.05(13) . . ? O1 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? O1 C2 H2C 109.2 . . ? C1 C2 H2C 109.2 . . ? H2B C2 H2C 107.9 . . ? O1 C3 C4 116.54(14) . . ? O1 C3 C8 123.05(15) . . ? C4 C3 C8 120.36(15) . . ? C3 C4 C5 120.12(16) . . ? C3 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? C6 C5 C4 120.54(17) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C7 119.68(17) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? C6 C7 C8 121.07(16) . . ? C6 C7 H7A 119.5 . . ? C8 C7 H7A 119.5 . . ? C7 C8 C3 118.20(15) . . ? C7 C8 C9 127.41(14) . . ? C3 C8 C9 114.38(13) . . ? N3 C9 C1 103.98(13) . . ? N3 C9 C8 133.88(12) . . ? C1 C9 C8 122.10(13) . . ? C15 C10 C11 122.92(13) . . ? C15 C10 N3 117.62(12) . . ? C11 C10 N3 119.45(12) . . ? C10 C11 C12 118.35(13) . . ? C10 C11 H11A 120.8 . . ? C12 C11 H11A 120.8 . . ? O2 C12 C13 115.40(12) . . ? O2 C12 C11 124.38(12) . . ? C13 C12 C11 120.22(13) . . ? O3 C13 C12 119.99(12) . . ? O3 C13 C14 120.22(12) . . ? C12 C13 C14 119.71(13) . . ? O4 C14 C15 124.13(13) . . ? O4 C14 C13 115.41(13) . . ? C15 C14 C13 120.45(13) . . ? C10 C15 C14 118.32(13) . . ? C10 C15 H15A 120.8 . . ? C14 C15 H15A 120.8 . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.223 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.034