Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Hitoshi Yamamoto' _publ_contact_author_email JIN@CHEM.SCI.OSAKA-U.AC.JP _publ_section_title ; Photoinduced switching of intramolecular hydrogen bond between amide NH and carboxyl oxygen ; loop_ _publ_author_name 'Norikazu Ueyama' 'Takashi Matsuhira' 'Takaaki Okamura' # Attachment 'E-1.cif' data_shelxl1 _database_code_depnum_ccdc_archive 'CCDC 603981' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H17 N O3' _chemical_formula_sum 'C14 H17 N O3' _chemical_formula_weight 247.29 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 triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.334(4) _cell_length_b 9.149(7) _cell_length_c 13.947(13) _cell_angle_alpha 74.60(3) _cell_angle_beta 80.12(3) _cell_angle_gamma 82.77(2) _cell_volume 644.1(9) _cell_formula_units_Z 2 _cell_measurement_temperature 200 _cell_measurement_reflns_used 3846 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.090 _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 200 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6236 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0823 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2883 _reflns_number_gt 1441 _reflns_threshold_expression I>2\s(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0220P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2883 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 O01 O 1.3610(2) 0.68460(13) 0.46347(10) 0.0516(4) Uani 1 1 d . . . H01 H 1.4842 0.6203 0.4547 0.062 Uiso 1 1 calc R . . O02 O 1.2257(2) 0.48600(13) 0.58459(9) 0.0464(4) Uani 1 1 d . . . O03 O 0.02543(19) 0.47214(12) 0.84455(9) 0.0367(3) Uani 1 1 d . . . N1 N 0.4322(2) 0.54338(13) 0.80844(9) 0.0287(3) Uani 1 1 d . . . H1 H 0.5920 0.5104 0.8152 0.034 Uiso 1 1 calc R . . C1 C 1.1988(3) 0.62377(19) 0.53797(13) 0.0338(4) Uani 1 1 d . . . C2 C 0.9799(3) 0.72306(18) 0.56694(12) 0.0356(4) Uani 1 1 d . . . H2 H 0.9708 0.8274 0.5317 0.043 Uiso 1 1 calc R . . C3 C 0.7933(3) 0.67500(17) 0.63981(12) 0.0311(4) Uani 1 1 d . . . H3 H 0.8067 0.5696 0.6723 0.037 Uiso 1 1 calc R . . C4 C 0.5687(3) 0.76474(17) 0.67645(12) 0.0274(4) Uani 1 1 d . . . C5 C 0.5233(3) 0.92034(18) 0.63151(13) 0.0352(4) Uani 1 1 d . . . H5 H 0.6464 0.9689 0.5788 0.042 Uiso 1 1 calc R . . C6 C 0.3060(3) 1.00476(18) 0.66135(13) 0.0378(5) Uani 1 1 d . . . H6 H 0.2794 1.1097 0.6291 0.045 Uiso 1 1 calc R . . C7 C 0.1269(3) 0.93603(17) 0.73848(13) 0.0372(5) Uani 1 1 d . . . H7 H -0.0250 0.9932 0.7586 0.045 Uiso 1 1 calc R . . C8 C 0.1685(3) 0.78405(17) 0.78651(12) 0.0328(4) Uani 1 1 d . . . H8 H 0.0464 0.7379 0.8405 0.039 Uiso 1 1 calc R . . C9 C 0.3869(3) 0.69811(16) 0.75663(11) 0.0258(4) Uani 1 1 d . . . C10 C 0.2547(3) 0.43981(17) 0.84900(12) 0.0270(4) Uani 1 1 d . . . C11 C 0.3669(3) 0.28240(16) 0.90049(12) 0.0262(4) Uani 1 1 d . . . C12 C 0.5725(3) 0.22041(18) 0.82704(13) 0.0374(5) Uani 1 1 d . . . H12A H 0.7166 0.2840 0.8086 0.045 Uiso 1 1 calc R . . H12B H 0.5010 0.2218 0.7666 0.045 Uiso 1 1 calc R . . H12C H 0.6315 0.1157 0.8590 0.045 Uiso 1 1 calc R . . C13 C 0.4755(3) 0.29588(17) 0.99253(12) 0.0340(4) Uani 1 1 d . . . H13A H 0.6177 0.3609 0.9704 0.041 Uiso 1 1 calc R . . H13B H 0.5367 0.1946 1.0297 0.041 Uiso 1 1 calc R . . H13C H 0.3415 0.3407 1.0363 0.041 Uiso 1 1 calc R . . C14 C 0.1585(3) 0.17203(17) 0.93610(13) 0.0398(5) Uani 1 1 d . . . H14A H 0.1024 0.1522 0.8777 0.048 Uiso 1 1 calc R . . H14B H 0.0133 0.2167 0.9754 0.048 Uiso 1 1 calc R . . H14C H 0.2260 0.0763 0.9781 0.048 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 O01 0.0412(8) 0.0478(8) 0.0506(9) -0.0042(7) 0.0197(7) -0.0009(6) O02 0.0450(8) 0.0382(7) 0.0429(8) -0.0001(6) 0.0084(6) 0.0029(6) O03 0.0233(6) 0.0376(7) 0.0458(8) -0.0037(6) -0.0067(5) -0.0020(5) N1 0.0198(7) 0.0289(7) 0.0330(9) -0.0014(6) -0.0022(6) -0.0020(6) C1 0.0294(9) 0.0434(11) 0.0271(11) -0.0081(9) 0.0013(8) -0.0062(9) C2 0.0343(9) 0.0327(9) 0.0343(11) -0.0043(8) 0.0021(9) -0.0015(8) C3 0.0306(9) 0.0310(9) 0.0283(10) -0.0037(8) -0.0013(8) -0.0021(8) C4 0.0250(8) 0.0327(9) 0.0239(10) -0.0067(8) -0.0024(7) -0.0021(8) C5 0.0364(10) 0.0337(10) 0.0315(11) -0.0017(8) -0.0023(8) -0.0046(9) C6 0.0425(11) 0.0275(9) 0.0415(12) -0.0060(8) -0.0088(9) 0.0020(9) C7 0.0336(9) 0.0343(10) 0.0453(13) -0.0176(9) -0.0038(9) 0.0054(9) C8 0.0304(9) 0.0362(10) 0.0317(11) -0.0128(8) 0.0028(8) -0.0036(9) C9 0.0256(8) 0.0283(9) 0.0249(10) -0.0078(8) -0.0062(7) -0.0014(8) C10 0.0239(9) 0.0321(9) 0.0253(10) -0.0087(7) -0.0005(7) -0.0043(8) C11 0.0203(8) 0.0259(8) 0.0319(10) -0.0064(7) -0.0031(7) -0.0025(7) C12 0.0311(9) 0.0387(10) 0.0445(12) -0.0164(9) -0.0039(9) 0.0004(8) C13 0.0318(9) 0.0330(9) 0.0343(11) -0.0041(8) -0.0045(8) -0.0023(8) C14 0.0288(9) 0.0305(9) 0.0573(13) -0.0041(9) -0.0071(9) -0.0051(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 O01 C1 1.2820(19) . ? O01 H01 0.8400 . ? O02 C1 1.258(2) . ? O03 C10 1.2297(18) . ? N1 C10 1.3679(18) . ? N1 C9 1.419(2) . ? N1 H1 0.8800 . ? C1 C2 1.455(2) . ? C2 C3 1.320(2) . ? C2 H2 0.9500 . ? C3 C4 1.462(2) . ? C3 H3 0.9500 . ? C4 C5 1.403(2) . ? C4 C9 1.406(2) . ? C5 C6 1.376(2) . ? C5 H5 0.9500 . ? C6 C7 1.380(2) . ? C6 H6 0.9500 . ? C7 C8 1.382(2) . ? C7 H7 0.9500 . ? C8 C9 1.388(2) . ? C8 H8 0.9500 . ? C10 C11 1.526(2) . ? C11 C14 1.526(2) . ? C11 C12 1.530(2) . ? C11 C13 1.535(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 C1 O01 H01 109.5 . . ? C10 N1 C9 127.18(13) . . ? C10 N1 H1 116.4 . . ? C9 N1 H1 116.4 . . ? O02 C1 O01 122.45(16) . . ? O02 C1 C2 121.13(15) . . ? O01 C1 C2 116.43(15) . . ? C3 C2 C1 123.11(16) . . ? C3 C2 H2 118.4 . . ? C1 C2 H2 118.4 . . ? C2 C3 C4 127.71(15) . . ? C2 C3 H3 116.1 . . ? C4 C3 H3 116.1 . . ? C5 C4 C9 117.37(15) . . ? C5 C4 C3 121.22(14) . . ? C9 C4 C3 121.40(14) . . ? C6 C5 C4 122.04(15) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C7 119.57(16) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C8 120.03(17) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 120.69(15) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C4 120.24(14) . . ? C8 C9 N1 120.32(14) . . ? C4 C9 N1 119.41(15) . . ? O03 C10 N1 122.51(15) . . ? O03 C10 C11 123.49(13) . . ? N1 C10 C11 113.99(13) . . ? C10 C11 C14 110.15(13) . . ? C10 C11 C12 110.29(14) . . ? C14 C11 C12 108.13(14) . . ? C10 C11 C13 108.19(13) . . ? C14 C11 C13 108.55(13) . . ? C12 C11 C13 111.52(14) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 O02 C1 C2 C3 -2.8(3) . . . . ? O01 C1 C2 C3 177.55(16) . . . . ? C1 C2 C3 C4 178.57(15) . . . . ? C2 C3 C4 C5 2.6(2) . . . . ? C2 C3 C4 C9 -178.71(16) . . . . ? C9 C4 C5 C6 -2.3(2) . . . . ? C3 C4 C5 C6 176.39(15) . . . . ? C4 C5 C6 C7 0.7(2) . . . . ? C5 C6 C7 C8 1.2(2) . . . . ? C6 C7 C8 C9 -1.4(2) . . . . ? C7 C8 C9 C4 -0.3(2) . . . . ? C7 C8 C9 N1 177.97(14) . . . . ? C5 C4 C9 C8 2.1(2) . . . . ? C3 C4 C9 C8 -176.60(14) . . . . ? C5 C4 C9 N1 -176.18(13) . . . . ? C3 C4 C9 N1 5.1(2) . . . . ? C10 N1 C9 C8 36.5(2) . . . . ? C10 N1 C9 C4 -145.24(16) . . . . ? C9 N1 C10 O03 -0.1(3) . . . . ? C9 N1 C10 C11 -179.63(14) . . . . ? O03 C10 C11 C14 4.8(2) . . . . ? N1 C10 C11 C14 -175.65(14) . . . . ? O03 C10 C11 C12 124.10(17) . . . . ? N1 C10 C11 C12 -56.38(18) . . . . ? O03 C10 C11 C13 -113.68(17) . . . . ? N1 C10 C11 C13 65.84(17) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.206 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.041 # Attachment 'Z-2.cif' data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 603982' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H28 N2 O3' _chemical_formula_sum 'C18 H28 N2 O3' _chemical_formula_weight 320.42 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 hexagonal _symmetry_space_group_name_H-M 'P 63 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' _cell_length_a 21.127(5) _cell_length_b 21.127(5) _cell_length_c 7.5223(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2907.8(12) _cell_formula_units_Z 6 _cell_measurement_temperature 200 _cell_measurement_reflns_used 18890 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.098 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1044 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_correction_T_max 0.985 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27887 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4440 _reflns_number_gt 3638 _reflns_threshold_expression I>2\s(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0483P)^2^+0.2749P] 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 noref _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 -0.2(10) _refine_ls_number_reflns 4440 _refine_ls_number_parameters 211 _refine_ls_number_restraints 139 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.014 _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 0.54729(7) 0.65887(6) 0.46508(18) 0.0551(3) Uani 1 1 d U . . O2 O 0.45663(7) 0.57856(6) 0.63470(18) 0.0557(3) Uani 1 1 d U . . O3 O 0.70876(7) 0.92278(7) 0.3694(2) 0.0646(4) Uani 1 1 d U . . N1 N 0.62335(7) 0.80383(7) 0.39782(18) 0.0421(3) Uani 1 1 d U . . H1 H 0.6091(10) 0.7602(10) 0.443(2) 0.051 Uiso 1 1 d . . . N2 N 0.58756(7) 0.60589(6) 0.02001(18) 0.0367(3) Uani 1 1 d U . . C1 C 0.49445(8) 0.64054(8) 0.56867(19) 0.0359(3) Uani 1 1 d U . . C2 C 0.47385(9) 0.69586(8) 0.6262(2) 0.0406(3) Uani 1 1 d U . . H2 H 0.4583 0.6921 0.7461 0.049 Uiso 1 1 calc R . . C3 C 0.47440(8) 0.74951(8) 0.5321(2) 0.0405(3) Uani 1 1 d U . . H3 H 0.4570 0.7770 0.5941 0.049 Uiso 1 1 calc R . . C4 C 0.49766(9) 0.77336(8) 0.3468(2) 0.0389(3) Uani 1 1 d U . . C5 C 0.44542(11) 0.77147(9) 0.2289(3) 0.0586(5) Uani 1 1 d U . . H5 H 0.3965 0.7528 0.2679 0.070 Uiso 1 1 calc R . . C6 C 0.46461(16) 0.79682(11) 0.0540(3) 0.0750(7) Uani 1 1 d U . . H6 H 0.4283 0.7933 -0.0265 0.090 Uiso 1 1 calc R . . C7 C 0.53538(16) 0.82647(11) -0.0007(3) 0.0714(7) Uani 1 1 d U . . H7 H 0.5483 0.8444 -0.1187 0.086 Uiso 1 1 calc R . . C8 C 0.58781(13) 0.83070(9) 0.1125(2) 0.0555(5) Uani 1 1 d U . . H8 H 0.6370 0.8521 0.0734 0.067 Uiso 1 1 calc R . . C9 C 0.56937(9) 0.80363(8) 0.28578(19) 0.0394(3) Uani 1 1 d U . . C10 C 0.69042(9) 0.86148(9) 0.4263(2) 0.0446(4) Uani 1 1 d U . . C11 C 0.74233(9) 0.84688(10) 0.5384(3) 0.0535(4) Uani 1 1 d U . . C12 C 0.71986(15) 0.84416(17) 0.7332(3) 0.0865(7) Uani 1 1 d U . . H12A H 0.7228 0.8905 0.7652 0.104 Uiso 1 1 calc R . . H12B H 0.7528 0.8362 0.8096 0.104 Uiso 1 1 calc R . . H12C H 0.6696 0.8041 0.7495 0.104 Uiso 1 1 calc R . . C13 C 0.73680(16) 0.77454(15) 0.4927(4) 0.0962(9) Uani 1 1 d U . . H13A H 0.6862 0.7351 0.5081 0.115 Uiso 1 1 calc R . . H13B H 0.7689 0.7662 0.5715 0.115 Uiso 1 1 calc R . . H13C H 0.7518 0.7755 0.3690 0.115 Uiso 1 1 calc R . . C14 C 0.81961(13) 0.90952(17) 0.5173(5) 0.1174(12) Uani 1 1 d U . . H14A H 0.8214 0.9555 0.5473 0.141 Uiso 1 1 calc R . . H14B H 0.8354 0.9115 0.3939 0.141 Uiso 1 1 calc R . . H14C H 0.8521 0.9022 0.5968 0.141 Uiso 1 1 calc R . . C15 C 0.60481(14) 0.68295(10) 0.0150(3) 0.0644(5) Uani 1 1 d U . . H15A H 0.5910 0.6955 0.1283 0.077 Uiso 1 1 calc R . . H15B H 0.5775 0.6894 -0.0819 0.077 Uiso 1 1 calc R . . H15C H 0.6573 0.7149 -0.0047 0.077 Uiso 1 1 calc R . . C16 C 0.60858(10) 0.58626(11) -0.1516(2) 0.0523(4) Uani 1 1 d U . . H16A H 0.6611 0.6184 -0.1718 0.063 Uiso 1 1 calc R . . H16B H 0.5811 0.5922 -0.2488 0.063 Uiso 1 1 calc R . . H16C H 0.5974 0.5353 -0.1470 0.063 Uiso 1 1 calc R . . C17 C 0.62901(10) 0.59677(9) 0.1689(2) 0.0478(4) Uani 1 1 d U . . H17A H 0.6148 0.6095 0.2815 0.057 Uiso 1 1 calc R . . H17B H 0.6815 0.6289 0.1496 0.057 Uiso 1 1 calc R . . H17C H 0.6179 0.5459 0.1735 0.057 Uiso 1 1 calc R . . C18 C 0.50782(9) 0.55704(11) 0.0498(3) 0.0600(5) Uani 1 1 d U . . H18A H 0.4938 0.5696 0.1630 0.072 Uiso 1 1 calc R . . H18B H 0.4966 0.5061 0.0534 0.072 Uiso 1 1 calc R . . H18C H 0.4805 0.5633 -0.0472 0.072 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 0.0700(8) 0.0429(6) 0.0650(8) 0.0130(6) 0.0244(7) 0.0376(6) O2 0.0530(7) 0.0344(6) 0.0798(9) 0.0127(6) 0.0047(6) 0.0220(6) O3 0.0618(8) 0.0407(7) 0.0885(10) 0.0135(7) 0.0021(7) 0.0235(6) N1 0.0462(8) 0.0385(7) 0.0464(7) 0.0147(6) 0.0090(6) 0.0247(6) N2 0.0408(7) 0.0335(6) 0.0416(7) 0.0019(5) 0.0014(6) 0.0230(5) C1 0.0403(8) 0.0309(7) 0.0371(8) 0.0012(6) -0.0061(6) 0.0182(6) C2 0.0453(9) 0.0325(7) 0.0423(8) 0.0011(7) 0.0072(7) 0.0182(7) C3 0.0408(8) 0.0328(7) 0.0515(9) -0.0020(7) 0.0034(7) 0.0212(7) C4 0.0512(9) 0.0279(7) 0.0451(8) -0.0048(6) -0.0090(7) 0.0254(7) C5 0.0674(12) 0.0373(9) 0.0794(14) -0.0103(9) -0.0298(10) 0.0325(9) C6 0.125(2) 0.0500(11) 0.0660(14) -0.0173(10) -0.0551(15) 0.0553(13) C7 0.133(2) 0.0465(11) 0.0433(10) -0.0012(8) -0.0188(12) 0.0514(13) C8 0.0960(15) 0.0392(9) 0.0384(9) 0.0023(7) 0.0044(9) 0.0392(10) C9 0.0598(10) 0.0311(7) 0.0346(7) 0.0013(6) -0.0007(7) 0.0283(7) C10 0.0483(9) 0.0427(9) 0.0477(9) 0.0067(7) 0.0131(7) 0.0264(8) C11 0.0477(9) 0.0541(10) 0.0621(11) 0.0061(9) 0.0043(9) 0.0280(8) C12 0.0991(19) 0.111(2) 0.0614(14) 0.0063(13) -0.0052(13) 0.0611(17) C13 0.106(2) 0.1073(19) 0.122(2) -0.0338(17) -0.0435(17) 0.0876(18) C14 0.0499(13) 0.119(2) 0.161(3) 0.056(2) 0.0016(17) 0.0251(14) C15 0.1044(16) 0.0418(9) 0.0579(11) 0.0013(9) -0.0110(11) 0.0449(11) C16 0.0481(10) 0.0713(12) 0.0489(10) -0.0127(9) -0.0051(8) 0.0385(9) C17 0.0558(10) 0.0436(9) 0.0466(9) -0.0024(7) -0.0136(8) 0.0269(8) C18 0.0391(9) 0.0741(12) 0.0693(12) 0.0199(11) 0.0095(9) 0.0302(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 1.2535(19) . ? O2 C1 1.2463(18) . ? O3 C10 1.228(2) . ? N1 C10 1.346(2) . ? N1 C9 1.416(2) . ? N1 H1 0.882(19) . ? N2 C15 1.481(2) . ? N2 C18 1.488(2) . ? N2 C16 1.490(2) . ? N2 C17 1.492(2) . ? C1 C2 1.500(2) . ? C2 C3 1.331(2) . ? C2 H2 0.9500 . ? C3 C4 1.480(2) . ? C3 H3 0.9500 . ? C4 C9 1.395(2) . ? C4 C5 1.401(2) . ? C5 C6 1.402(3) . ? C5 H5 0.9500 . ? C6 C7 1.364(3) . ? C6 H6 0.9500 . ? C7 C8 1.364(3) . ? C7 H7 0.9500 . ? C8 C9 1.398(2) . ? C8 H8 0.9500 . ? C10 C11 1.532(3) . ? C11 C14 1.511(3) . ? C11 C13 1.513(3) . ? C11 C12 1.533(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 C10 N1 C9 125.38(13) . . ? C10 N1 H1 122.6(12) . . ? C9 N1 H1 111.9(12) . . ? C15 N2 C18 109.71(14) . . ? C15 N2 C16 109.90(14) . . ? C18 N2 C16 109.22(14) . . ? C15 N2 C17 108.86(13) . . ? C18 N2 C17 109.34(13) . . ? C16 N2 C17 109.79(12) . . ? O2 C1 O1 125.19(14) . . ? O2 C1 C2 114.85(14) . . ? O1 C1 C2 119.93(13) . . ? C3 C2 C1 128.86(15) . . ? C3 C2 H2 115.6 . . ? C1 C2 H2 115.6 . . ? C2 C3 C4 130.59(14) . . ? C2 C3 H3 114.7 . . ? C4 C3 H3 114.7 . . ? C9 C4 C5 117.69(16) . . ? C9 C4 C3 124.43(14) . . ? C5 C4 C3 117.63(16) . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 119.98(19) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.6(2) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C9 120.3(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C4 C9 C8 120.71(16) . . ? C4 C9 N1 119.60(13) . . ? C8 C9 N1 119.63(16) . . ? O3 C10 N1 122.24(16) . . ? O3 C10 C11 121.58(16) . . ? N1 C10 C11 116.16(14) . . ? C14 C11 C13 111.4(2) . . ? C14 C11 C10 109.54(17) . . ? C13 C11 C10 112.14(17) . . ? C14 C11 C12 108.2(2) . . ? C13 C11 C12 108.3(2) . . ? C10 C11 C12 107.14(15) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 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 O2 C1 C2 C3 -143.87(17) . . . . ? O1 C1 C2 C3 37.7(2) . . . . ? C1 C2 C3 C4 -2.7(3) . . . . ? C2 C3 C4 C9 -65.7(2) . . . . ? C2 C3 C4 C5 120.27(19) . . . . ? C9 C4 C5 C6 2.3(2) . . . . ? C3 C4 C5 C6 176.71(14) . . . . ? C4 C5 C6 C7 -2.8(3) . . . . ? C5 C6 C7 C8 1.1(3) . . . . ? C6 C7 C8 C9 0.9(3) . . . . ? C5 C4 C9 C8 -0.3(2) . . . . ? C3 C4 C9 C8 -174.28(14) . . . . ? C5 C4 C9 N1 -177.30(14) . . . . ? C3 C4 C9 N1 8.7(2) . . . . ? C7 C8 C9 C4 -1.3(2) . . . . ? C7 C8 C9 N1 175.69(15) . . . . ? C10 N1 C9 C4 -133.42(16) . . . . ? C10 N1 C9 C8 49.5(2) . . . . ? C9 N1 C10 O3 7.5(3) . . . . ? C9 N1 C10 C11 -174.16(14) . . . . ? O3 C10 C11 C14 -16.8(3) . . . . ? N1 C10 C11 C14 164.8(2) . . . . ? O3 C10 C11 C13 -141.0(2) . . . . ? N1 C10 C11 C13 40.6(2) . . . . ? O3 C10 C11 C12 100.4(2) . . . . ? N1 C10 C11 C12 -78.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.119 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.026