# 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 'Prof Hitoshi Yamamoto' _publ_contact_author_email MATSU@CHEM.SCI.OSAKA-U.AC.JP _publ_section_title ; Novel photosystem involving protonation and deprotonation process modeled on PYP photocycle ; _publ_contact_author_address ; Science Osaka University Machikaneyamacho1-1 Toyonaka 560-0043 ; loop_ _publ_author_name 'Hitoshi Yamamoto' 'Takashi Matsuhira' 'Taka-aki Okamura' 'Kazuki Tsuchihashi' 'Norikazu Ueyama' # Attachment 'Z-1.cif' data_shelxl_2 _database_code_depnum_ccdc_archive 'CCDC 684897' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C13 H17 N O2' _chemical_formula_sum ' C13 H17 N O2' _chemical_formula_weight 219.28 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.000(6) _cell_length_b 12.348(6) _cell_length_c 9.398(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.58(2) _cell_angle_gamma 90.00 _cell_volume 1240.8(13) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 5348 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.079 _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(2) _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 11384 _diffrn_reflns_av_R_equivalents 0.0885 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2835 _reflns_number_gt 1705 _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^)+(0.0367P)^2^+0.4805P] 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 2835 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1291 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.1290 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 O01 O 0.55974(14) 0.43812(12) 0.17240(18) 0.0413(4) Uani 1 1 d . . . H01 H 0.507(2) 0.3819(19) 0.144(3) 0.050 Uiso 1 1 d . . . O02 O 0.43006(14) 0.27946(11) 0.05640(17) 0.0416(4) Uani 1 1 d . . . N1 N 0.37465(17) 0.10782(14) 0.0982(2) 0.0366(5) Uani 1 1 d . . . H1 H 0.396(2) 0.0493(18) 0.153(3) 0.044 Uiso 1 1 d . . . C1 C 0.6739(2) 0.40946(17) 0.1509(2) 0.0350(5) Uani 1 1 d . . . C2 C 0.7391(2) 0.48731(18) 0.0923(3) 0.0414(6) Uani 1 1 d . . . H2 H 0.7010 0.5552 0.0624 0.050 Uiso 1 1 calc R . . C3 C 0.8579(2) 0.4669(2) 0.0774(3) 0.0489(6) Uani 1 1 d . . . H3 H 0.9018 0.5207 0.0374 0.059 Uiso 1 1 calc R . . C4 C 0.9143(2) 0.3680(2) 0.1202(3) 0.0492(6) Uani 1 1 d . . . H4 H 0.9962 0.3532 0.1087 0.059 Uiso 1 1 calc R . . C5 C 0.8499(2) 0.29157(18) 0.1798(3) 0.0407(6) Uani 1 1 d . . . H5 H 0.8898 0.2247 0.2118 0.049 Uiso 1 1 calc R . . C6 C 0.72794(19) 0.30855(16) 0.1949(2) 0.0337(5) Uani 1 1 d . . . C7 C 0.6727(2) 0.22474(17) 0.2733(3) 0.0388(5) Uani 1 1 d . . . H7 H 0.7296 0.1990 0.3589 0.047 Uiso 1 1 calc R . . C8 C 0.5607(2) 0.17742(17) 0.2505(3) 0.0381(5) Uani 1 1 d . . . H8 H 0.5505 0.1266 0.3227 0.046 Uiso 1 1 calc R . . C9 C 0.4507(2) 0.19342(17) 0.1280(2) 0.0345(5) Uani 1 1 d . . . C10 C 0.2603(2) 0.10082(18) -0.0204(2) 0.0385(5) Uani 1 1 d . . . C11 C 0.1652(2) 0.1835(2) 0.0044(3) 0.0533(7) Uani 1 1 d . . . H11A H 0.1458 0.1703 0.0995 0.064 Uiso 1 1 calc R . . H11B H 0.0886 0.1770 -0.0734 0.064 Uiso 1 1 calc R . . H11C H 0.1998 0.2565 0.0029 0.064 Uiso 1 1 calc R . . C12 C 0.2077(2) -0.01303(19) -0.0148(3) 0.0558(7) Uani 1 1 d . . . H12A H 0.2691 -0.0664 -0.0308 0.067 Uiso 1 1 calc R . . H12B H 0.1305 -0.0206 -0.0914 0.067 Uiso 1 1 calc R . . H12C H 0.1897 -0.0252 0.0812 0.067 Uiso 1 1 calc R . . C13 C 0.2931(2) 0.1181(2) -0.1674(3) 0.0538(7) Uani 1 1 d . . . H13A H 0.3545 0.0637 -0.1803 0.065 Uiso 1 1 calc R . . H13B H 0.3286 0.1907 -0.1702 0.065 Uiso 1 1 calc R . . H13C H 0.2175 0.1111 -0.2463 0.065 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 0.0388(9) 0.0343(9) 0.0525(11) -0.0055(7) 0.0143(8) -0.0017(7) O02 0.0465(9) 0.0349(8) 0.0403(10) 0.0061(7) 0.0042(8) -0.0021(7) N1 0.0394(11) 0.0332(10) 0.0350(11) 0.0034(8) 0.0045(9) -0.0032(9) C1 0.0358(12) 0.0370(12) 0.0313(12) -0.0038(9) 0.0061(10) -0.0013(10) C2 0.0441(14) 0.0386(12) 0.0405(14) 0.0037(10) 0.0080(11) -0.0011(11) C3 0.0449(14) 0.0520(15) 0.0508(16) 0.0082(12) 0.0132(12) -0.0076(13) C4 0.0365(13) 0.0586(16) 0.0537(17) 0.0008(12) 0.0132(12) -0.0016(12) C5 0.0380(13) 0.0401(12) 0.0412(15) -0.0017(10) 0.0034(11) 0.0016(11) C6 0.0359(12) 0.0370(12) 0.0261(12) -0.0038(9) 0.0032(10) -0.0037(10) C7 0.0422(13) 0.0384(12) 0.0328(13) 0.0040(10) 0.0025(10) 0.0005(11) C8 0.0439(13) 0.0372(12) 0.0332(13) 0.0045(10) 0.0091(10) -0.0018(11) C9 0.0367(12) 0.0358(12) 0.0332(13) -0.0008(9) 0.0128(10) 0.0017(10) C10 0.0398(12) 0.0411(12) 0.0321(13) -0.0003(10) 0.0033(10) -0.0037(11) C11 0.0446(15) 0.0578(16) 0.0539(18) -0.0079(12) 0.0046(13) 0.0009(12) C12 0.0614(17) 0.0483(15) 0.0504(17) 0.0007(12) -0.0014(13) -0.0136(13) C13 0.0592(16) 0.0674(17) 0.0333(14) -0.0009(12) 0.0080(12) -0.0050(14) _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 1.365(3) . ? O01 H01 0.91(2) . ? O02 C9 1.250(2) . ? N1 C9 1.336(3) . ? N1 C10 1.474(3) . ? N1 H1 0.88(2) . ? C1 C2 1.387(3) . ? C1 C6 1.401(3) . ? C2 C3 1.371(3) . ? C2 H2 0.9500 . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.375(3) . ? C4 H4 0.9500 . ? C5 C6 1.397(3) . ? C5 H5 0.9500 . ? C6 C7 1.481(3) . ? C7 C8 1.334(3) . ? C7 H7 0.9500 . ? C8 C9 1.474(3) . ? C8 H8 0.9500 . ? C10 C11 1.518(3) . ? C10 C13 1.523(3) . ? C10 C12 1.526(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 108.1(14) . . ? C9 N1 C10 125.86(19) . . ? C9 N1 H1 117.0(15) . . ? C10 N1 H1 117.1(15) . . ? O01 C1 C2 117.26(19) . . ? O01 C1 C6 121.87(19) . . ? C2 C1 C6 120.7(2) . . ? C3 C2 C1 120.4(2) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.3(2) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.0(2) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 122.5(2) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C5 C6 C1 117.00(19) . . ? C5 C6 C7 117.50(19) . . ? C1 C6 C7 125.00(19) . . ? C8 C7 C6 134.2(2) . . ? C8 C7 H7 112.9 . . ? C6 C7 H7 112.9 . . ? C7 C8 C9 128.6(2) . . ? C7 C8 H8 115.7 . . ? C9 C8 H8 115.7 . . ? O02 C9 N1 122.3(2) . . ? O02 C9 C8 123.1(2) . . ? N1 C9 C8 114.60(19) . . ? N1 C10 C11 109.93(19) . . ? N1 C10 C13 109.60(19) . . ? C11 C10 C13 111.3(2) . . ? N1 C10 C12 106.94(18) . . ? C11 C10 C12 109.5(2) . . ? C13 C10 C12 109.5(2) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 O01 C1 C2 C3 175.4(2) . . . . ? C6 C1 C2 C3 -0.4(3) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C3 C4 C5 C6 1.9(4) . . . . ? C4 C5 C6 C1 -2.1(3) . . . . ? C4 C5 C6 C7 -174.3(2) . . . . ? O01 C1 C6 C5 -174.3(2) . . . . ? C2 C1 C6 C5 1.3(3) . . . . ? O01 C1 C6 C7 -2.6(3) . . . . ? C2 C1 C6 C7 172.9(2) . . . . ? C5 C6 C7 C8 -137.4(3) . . . . ? C1 C6 C7 C8 51.1(4) . . . . ? C6 C7 C8 C9 2.1(4) . . . . ? C10 N1 C9 O02 1.0(3) . . . . ? C10 N1 C9 C8 -178.33(19) . . . . ? C7 C8 C9 O02 -27.0(4) . . . . ? C7 C8 C9 N1 152.3(2) . . . . ? C9 N1 C10 C11 -63.2(3) . . . . ? C9 N1 C10 C13 59.5(3) . . . . ? C9 N1 C10 C12 178.0(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 0.190 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.039 # Attachment 'E-1.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 684898' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C13 H17 N O2' _chemical_formula_sum ' C13 H17 N O2' _chemical_formula_weight 219.28 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 12.940(5) _cell_length_b 9.252(5) _cell_length_c 20.599(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2466(2) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 5771 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 27.5 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.020 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.600 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _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 17209 _diffrn_reflns_av_R_equivalents 0.1264 _diffrn_reflns_av_sigmaI/netI 0.0638 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2161 _reflns_number_gt 1396 _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^)+(0.0518P)^2^+0.5737P] 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 2161 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1008 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1276 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 O01 O 0.47568(13) 0.2211(2) 0.21052(9) 0.0440(5) Uani 1 1 d . . . H01 H 0.4194(19) 0.276(3) 0.2052(12) 0.053 Uiso 1 1 d . . . O02 O 0.69529(12) -0.13874(19) 0.32092(8) 0.0436(5) Uani 1 1 d . . . N1 N 0.85926(14) -0.0563(2) 0.33126(10) 0.0353(5) Uani 1 1 d . . . H1 H 0.9015(18) 0.010(3) 0.3166(11) 0.042 Uiso 1 1 d . . . C1 C 0.55291(17) 0.2640(3) 0.16920(12) 0.0353(6) Uani 1 1 d . . . C2 C 0.53655(19) 0.3691(3) 0.12271(12) 0.0425(7) Uani 1 1 d . . . H2 H 0.4706 0.4134 0.1189 0.051 Uiso 1 1 calc R . . C3 C 0.6158(2) 0.4101(3) 0.08173(12) 0.0470(7) Uani 1 1 d . . . H3 H 0.6043 0.4831 0.0501 0.056 Uiso 1 1 calc R . . C4 C 0.7114(2) 0.3453(3) 0.08657(13) 0.0451(7) Uani 1 1 d . . . H4 H 0.7661 0.3739 0.0586 0.054 Uiso 1 1 calc R . . C5 C 0.72707(18) 0.2392(3) 0.13220(12) 0.0402(7) Uani 1 1 d . . . H5 H 0.7930 0.1944 0.1348 0.048 Uiso 1 1 calc R . . C6 C 0.64930(17) 0.1950(3) 0.17491(12) 0.0329(6) Uani 1 1 d . . . C7 C 0.66612(17) 0.0852(3) 0.22453(11) 0.0339(6) Uani 1 1 d . . . H7 H 0.6064 0.0427 0.2434 0.041 Uiso 1 1 calc R . . C8 C 0.75724(17) 0.0389(3) 0.24576(12) 0.0343(6) Uani 1 1 d . . . H8 H 0.8181 0.0711 0.2244 0.041 Uiso 1 1 calc R . . C9 C 0.76702(17) -0.0608(3) 0.30134(11) 0.0328(6) Uani 1 1 d . . . C10 C 0.88743(17) -0.1268(3) 0.39327(11) 0.0354(6) Uani 1 1 d . . . C11 C 0.8183(2) -0.0721(4) 0.44735(13) 0.0632(9) Uani 1 1 d . . . H11A H 0.7466 -0.0999 0.4385 0.076 Uiso 1 1 calc R . . H11B H 0.8232 0.0335 0.4499 0.076 Uiso 1 1 calc R . . H11C H 0.8404 -0.1144 0.4887 0.076 Uiso 1 1 calc R . . C12 C 0.9987(2) -0.0849(4) 0.40702(14) 0.0689(10) Uani 1 1 d . . . H12A H 1.0037 0.0204 0.4113 0.083 Uiso 1 1 calc R . . H12B H 1.0428 -0.1173 0.3712 0.083 Uiso 1 1 calc R . . H12C H 1.0214 -0.1306 0.4475 0.083 Uiso 1 1 calc R . . C13 C 0.8805(2) -0.2891(3) 0.38698(14) 0.0631(9) Uani 1 1 d . . . H13A H 0.8088 -0.3169 0.3782 0.076 Uiso 1 1 calc R . . H13B H 0.9036 -0.3343 0.4275 0.076 Uiso 1 1 calc R . . H13C H 0.9246 -0.3214 0.3512 0.076 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 0.0309(9) 0.0396(12) 0.0615(12) 0.0103(10) 0.0022(9) 0.0057(8) O02 0.0358(9) 0.0401(11) 0.0549(11) 0.0053(9) -0.0054(8) -0.0081(8) N1 0.0325(11) 0.0342(13) 0.0391(12) 0.0040(10) -0.0024(9) -0.0036(9) C1 0.0347(13) 0.0277(15) 0.0435(14) -0.0034(12) -0.0017(12) -0.0018(11) C2 0.0417(14) 0.0329(16) 0.0530(17) 0.0015(14) -0.0072(13) 0.0064(12) C3 0.0563(17) 0.0408(18) 0.0439(16) 0.0087(14) -0.0052(14) -0.0004(14) C4 0.0469(16) 0.0457(18) 0.0427(16) 0.0044(14) 0.0042(13) -0.0051(13) C5 0.0371(14) 0.0416(17) 0.0418(14) -0.0027(13) -0.0010(12) 0.0034(12) C6 0.0339(13) 0.0279(14) 0.0369(13) -0.0040(12) -0.0009(11) 0.0014(11) C7 0.0298(12) 0.0296(15) 0.0424(15) -0.0058(12) 0.0011(11) -0.0036(10) C8 0.0309(12) 0.0343(15) 0.0376(13) -0.0033(12) 0.0034(11) -0.0007(11) C9 0.0308(13) 0.0283(14) 0.0392(14) -0.0057(11) -0.0010(11) 0.0024(11) C10 0.0369(13) 0.0337(16) 0.0354(14) 0.0018(11) -0.0049(11) -0.0011(11) C11 0.081(2) 0.068(2) 0.0408(16) -0.0013(16) 0.0012(15) 0.0217(18) C12 0.0549(18) 0.086(3) 0.066(2) 0.0274(19) -0.0224(16) -0.0170(17) C13 0.093(2) 0.0371(19) 0.0598(19) 0.0014(15) -0.0266(17) 0.0083(16) _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 1.371(3) . ? O01 H01 0.90(3) . ? O02 C9 1.243(3) . ? N1 C9 1.344(3) . ? N1 C10 1.480(3) . ? N1 H1 0.87(3) . ? C1 C2 1.381(3) . ? C1 C6 1.406(3) . ? C2 C3 1.381(3) . ? C2 H2 0.9500 . ? C3 C4 1.379(3) . ? C3 H3 0.9500 . ? C4 C5 1.374(4) . ? C4 H4 0.9500 . ? C5 C6 1.398(3) . ? C5 H5 0.9500 . ? C6 C7 1.458(3) . ? C7 C8 1.328(3) . ? C7 H7 0.9500 . ? C8 C9 1.476(3) . ? C8 H8 0.9500 . ? C10 C13 1.510(4) . ? C10 C11 1.516(4) . ? C10 C12 1.518(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 110.7(17) . . ? C9 N1 C10 127.0(2) . . ? C9 N1 H1 114.8(16) . . ? C10 N1 H1 116.9(16) . . ? O01 C1 C2 121.5(2) . . ? O01 C1 C6 117.6(2) . . ? C2 C1 C6 120.9(2) . . ? C3 C2 C1 120.2(2) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.5(2) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 122.2(2) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 116.9(2) . . ? C5 C6 C7 122.5(2) . . ? C1 C6 C7 120.5(2) . . ? C8 C7 C6 126.0(2) . . ? C8 C7 H7 117.0 . . ? C6 C7 H7 117.0 . . ? C7 C8 C9 122.2(2) . . ? C7 C8 H8 118.9 . . ? C9 C8 H8 118.9 . . ? O02 C9 N1 122.2(2) . . ? O02 C9 C8 123.4(2) . . ? N1 C9 C8 114.4(2) . . ? N1 C10 C13 110.4(2) . . ? N1 C10 C11 110.0(2) . . ? C13 C10 C11 111.1(2) . . ? N1 C10 C12 106.40(19) . . ? C13 C10 C12 109.1(2) . . ? C11 C10 C12 109.7(2) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.165 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.040