# Electronic Supplementary Material (ESI) for Photochemical and Photobiological Science # This journal is © The Royal Society of Chemistry and Owner Societies 2011 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_cambridge 0171 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Miguel A Garcia-Garibay' _publ_contact_author_email MGG@CHEM.UCLA.EDU loop_ _publ_author_name M.A.Garcia-Garibay A.Natarajan S.Shiraki data_gg0307s _database_code_depnum_ccdc_archive 'CCDC 814323' #TrackingRef '- CCDC 814323.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 N2 O' _chemical_formula_sum 'C19 H16 N2 O' _chemical_formula_weight 288.34 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.154(2) _cell_length_b 7.971(2) _cell_length_c 12.393(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.930(3) _cell_angle_gamma 90.00 _cell_volume 778.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4571 _cell_measurement_theta_min 4.26 _cell_measurement_theta_max 28.26 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9462 _exptl_absorpt_correction_T_max 0.9847 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Phi and Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6915 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.26 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2050 _reflns_number_gt 1960 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0493P)^2^+0.0939P] 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 ? _refine_ls_number_reflns 2050 _refine_ls_number_parameters 201 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0803 _refine_ls_wR_factor_gt 0.0789 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.53312(14) 0.40134(16) 0.59127(10) 0.0291(3) Uani 1 1 d . . . N1 N 0.81373(17) 0.3089(2) 0.95535(11) 0.0262(3) Uani 1 1 d . . . N2 N 1.07527(16) 0.51927(19) 0.76221(11) 0.0259(3) Uani 1 1 d . . . C1 C 0.64986(17) 0.4049(2) 0.67298(11) 0.0183(3) Uani 1 1 d . . . C2 C 0.74671(17) 0.57143(18) 0.70875(11) 0.0166(3) Uani 1 1 d . . . C3 C 0.68637(17) 0.64798(18) 0.80555(11) 0.0165(3) Uani 1 1 d . . . C4 C 0.51550(18) 0.63684(19) 0.80559(12) 0.0198(3) Uani 1 1 d . . . H4 H 0.4381 0.5776 0.7477 0.024 Uiso 1 1 calc R . . C5 C 0.45851(19) 0.7125(2) 0.89055(13) 0.0234(3) Uani 1 1 d . . . H5 H 0.3428 0.7027 0.8915 0.028 Uiso 1 1 calc R . . C6 C 0.5704(2) 0.8022(2) 0.97374(13) 0.0253(3) Uani 1 1 d . . . H6 H 0.5311 0.8550 1.0311 0.030 Uiso 1 1 calc R . . C7 C 0.7401(2) 0.8149(2) 0.97315(13) 0.0250(3) Uani 1 1 d . . . H7 H 0.8166 0.8767 1.0301 0.030 Uiso 1 1 calc R . . C8 C 0.79841(19) 0.7376(2) 0.88967(12) 0.0206(3) Uani 1 1 d . . . H8 H 0.9147 0.7458 0.8899 0.025 Uiso 1 1 calc R . . C9 C 0.93180(18) 0.53909(19) 0.74205(11) 0.0182(3) Uani 1 1 d . . . C10 C 0.7099(2) 0.6950(2) 0.60996(12) 0.0232(3) Uani 1 1 d . . . H10A H 0.7718 0.7999 0.6330 0.035 Uiso 1 1 calc R . . H10B H 0.5878 0.7182 0.5863 0.035 Uiso 1 1 calc R . . H10C H 0.7466 0.6457 0.5476 0.035 Uiso 1 1 calc R . . C11 C 0.70282(17) 0.24188(19) 0.74202(12) 0.0181(3) Uani 1 1 d . . . C12 C 0.84242(18) 0.15393(19) 0.69896(13) 0.0195(3) Uani 1 1 d . . . C13 C 0.8200(2) 0.1353(2) 0.58445(14) 0.0252(3) Uani 1 1 d . . . H13 H 0.7222 0.1808 0.5340 0.030 Uiso 1 1 calc R . . C14 C 0.9406(2) 0.0504(2) 0.54366(16) 0.0328(4) Uani 1 1 d . . . H14 H 0.9251 0.0380 0.4654 0.039 Uiso 1 1 calc R . . C15 C 1.0831(2) -0.0160(2) 0.61730(17) 0.0345(4) Uani 1 1 d . . . H15 H 1.1655 -0.0739 0.5895 0.041 Uiso 1 1 calc R . . C16 C 1.1060(2) 0.0018(2) 0.73122(17) 0.0316(4) Uani 1 1 d . . . H16 H 1.2038 -0.0442 0.7815 0.038 Uiso 1 1 calc R . . C17 C 0.98588(19) 0.0869(2) 0.77239(14) 0.0241(3) Uani 1 1 d . . . H17 H 1.0019 0.0992 0.8507 0.029 Uiso 1 1 calc R . . C18 C 0.76699(18) 0.28217(19) 0.86240(12) 0.0200(3) Uani 1 1 d . . . C19 C 0.54654(19) 0.1260(2) 0.72725(15) 0.0255(3) Uani 1 1 d . . . H19A H 0.5791 0.0241 0.7719 0.038 Uiso 1 1 calc R . . H19B H 0.5042 0.0957 0.6483 0.038 Uiso 1 1 calc R . . H19C H 0.4573 0.1848 0.7522 0.038 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 0.0314(6) 0.0214(5) 0.0260(6) -0.0033(5) -0.0077(4) 0.0013(5) N1 0.0243(6) 0.0317(7) 0.0233(6) 0.0053(6) 0.0072(5) 0.0035(6) N2 0.0229(6) 0.0268(7) 0.0290(7) 0.0013(6) 0.0082(5) -0.0016(6) C1 0.0199(6) 0.0165(6) 0.0184(6) -0.0008(5) 0.0047(5) 0.0015(5) C2 0.0170(6) 0.0165(6) 0.0158(6) 0.0004(5) 0.0035(5) 0.0004(5) C3 0.0197(6) 0.0143(6) 0.0154(6) 0.0009(5) 0.0044(5) 0.0010(5) C4 0.0186(6) 0.0180(7) 0.0221(7) -0.0005(6) 0.0042(5) -0.0007(5) C5 0.0217(6) 0.0226(7) 0.0284(7) 0.0016(6) 0.0108(6) 0.0012(6) C6 0.0324(8) 0.0231(7) 0.0229(7) -0.0009(6) 0.0116(6) 0.0027(7) C7 0.0288(7) 0.0239(7) 0.0212(7) -0.0046(6) 0.0044(6) -0.0013(6) C8 0.0204(7) 0.0203(7) 0.0206(7) -0.0011(6) 0.0044(5) -0.0017(6) C9 0.0207(6) 0.0170(7) 0.0176(6) 0.0003(5) 0.0061(5) -0.0020(5) C10 0.0310(8) 0.0191(7) 0.0201(7) 0.0045(5) 0.0078(6) 0.0022(6) C11 0.0177(6) 0.0167(6) 0.0196(6) 0.0012(5) 0.0044(5) -0.0006(5) C12 0.0201(6) 0.0129(6) 0.0274(7) 0.0011(5) 0.0094(5) -0.0014(5) C13 0.0304(7) 0.0214(7) 0.0262(7) 0.0025(6) 0.0118(6) -0.0006(6) C14 0.0433(9) 0.0266(9) 0.0365(9) -0.0020(7) 0.0247(8) -0.0025(7) C15 0.0350(8) 0.0231(8) 0.0547(11) -0.0026(8) 0.0281(8) 0.0009(7) C16 0.0241(7) 0.0219(8) 0.0505(10) 0.0034(7) 0.0128(7) 0.0035(6) C17 0.0215(7) 0.0194(7) 0.0312(8) 0.0012(6) 0.0067(6) 0.0005(6) C18 0.0177(6) 0.0194(7) 0.0236(7) 0.0046(5) 0.0067(5) 0.0009(5) C19 0.0216(7) 0.0217(8) 0.0336(8) -0.0003(6) 0.0079(6) -0.0050(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.1982(18) . ? N1 C18 1.136(2) . ? N2 C9 1.142(2) . ? C1 C2 1.550(2) . ? C1 C11 1.554(2) . ? C2 C9 1.4810(19) . ? C2 C3 1.5356(19) . ? C2 C10 1.540(2) . ? C3 C8 1.393(2) . ? C3 C4 1.3961(19) . ? C4 C5 1.393(2) . ? C4 H4 0.9500 . ? C5 C6 1.386(2) . ? C5 H5 0.9500 . ? C6 C7 1.389(2) . ? C6 H6 0.9500 . ? C7 C8 1.389(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C18 1.483(2) . ? C11 C12 1.544(2) . ? C11 C19 1.546(2) . ? C12 C13 1.391(2) . ? C12 C17 1.391(2) . ? C13 C14 1.392(2) . ? C13 H13 0.9500 . ? C14 C15 1.385(3) . ? C14 H14 0.9500 . ? C15 C16 1.383(3) . ? C15 H15 0.9500 . ? C16 C17 1.392(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 O1 C1 C2 119.81(14) . . ? O1 C1 C11 119.54(14) . . ? C2 C1 C11 120.65(11) . . ? C9 C2 C3 111.10(11) . . ? C9 C2 C10 108.00(11) . . ? C3 C2 C10 109.32(12) . . ? C9 C2 C1 109.76(12) . . ? C3 C2 C1 108.76(11) . . ? C10 C2 C1 109.88(11) . . ? C8 C3 C4 119.63(13) . . ? C8 C3 C2 120.53(12) . . ? C4 C3 C2 119.71(12) . . ? C5 C4 C3 119.99(14) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 120.11(14) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 119.95(14) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C8 120.26(14) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C3 120.05(14) . . ? C7 C8 H8 120.0 . . ? C3 C8 H8 120.0 . . ? N2 C9 C2 175.92(15) . . ? C2 C10 H10A 109.5 . . ? C2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C18 C11 C12 110.21(12) . . ? C18 C11 C19 108.35(12) . . ? C12 C11 C19 110.26(13) . . ? C18 C11 C1 110.40(12) . . ? C12 C11 C1 108.31(11) . . ? C19 C11 C1 109.30(12) . . ? C13 C12 C17 119.59(14) . . ? C13 C12 C11 119.09(13) . . ? C17 C12 C11 121.26(14) . . ? C12 C13 C14 120.21(16) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.87(16) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 120.20(15) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.14(16) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 120.00(16) . . ? C12 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? N1 C18 C11 177.97(16) . . ? C11 C19 H19A 109.5 . . ? C11 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C11 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 O1 C1 C2 C9 -136.66(15) . . . . ? C11 C1 C2 C9 43.23(17) . . . . ? O1 C1 C2 C3 101.60(16) . . . . ? C11 C1 C2 C3 -78.51(15) . . . . ? O1 C1 C2 C10 -18.03(19) . . . . ? C11 C1 C2 C10 161.86(12) . . . . ? C9 C2 C3 C8 25.23(18) . . . . ? C10 C2 C3 C8 -93.87(16) . . . . ? C1 C2 C3 C8 146.15(13) . . . . ? C9 C2 C3 C4 -158.84(13) . . . . ? C10 C2 C3 C4 82.05(16) . . . . ? C1 C2 C3 C4 -37.92(17) . . . . ? C8 C3 C4 C5 -1.2(2) . . . . ? C2 C3 C4 C5 -177.11(13) . . . . ? C3 C4 C5 C6 1.5(2) . . . . ? C4 C5 C6 C7 -0.8(2) . . . . ? C5 C6 C7 C8 -0.2(2) . . . . ? C6 C7 C8 C3 0.5(2) . . . . ? C4 C3 C8 C7 0.2(2) . . . . ? C2 C3 C8 C7 176.09(14) . . . . ? O1 C1 C11 C18 -146.61(15) . . . . ? C2 C1 C11 C18 33.50(17) . . . . ? O1 C1 C11 C12 92.64(17) . . . . ? C2 C1 C11 C12 -87.26(15) . . . . ? O1 C1 C11 C19 -27.52(19) . . . . ? C2 C1 C11 C19 152.59(12) . . . . ? C18 C11 C12 C13 -167.47(14) . . . . ? C19 C11 C12 C13 72.96(17) . . . . ? C1 C11 C12 C13 -46.60(18) . . . . ? C18 C11 C12 C17 15.4(2) . . . . ? C19 C11 C12 C17 -104.21(16) . . . . ? C1 C11 C12 C17 136.23(14) . . . . ? C17 C12 C13 C14 -0.1(2) . . . . ? C11 C12 C13 C14 -177.32(14) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C14 C15 C16 C17 -0.2(3) . . . . ? C13 C12 C17 C16 0.0(2) . . . . ? C11 C12 C17 C16 177.15(14) . . . . ? C15 C16 C17 C12 0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.288 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.036 # Attachment '- CCDC 814324.cif' data_gg2407s _database_code_depnum_ccdc_archive 'CCDC 814324' #TrackingRef '- CCDC 814324.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H20 N2 O' _chemical_formula_sum 'C21 H20 N2 O' _chemical_formula_weight 316.39 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 7.3178(14) _cell_length_b 14.158(3) _cell_length_c 17.191(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.227(2) _cell_angle_gamma 90.00 _cell_volume 1770.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3181 _cell_measurement_theta_min 4.13 _cell_measurement_theta_max 25.69 _exptl_crystal_description block _exptl_crystal_colour clear _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9461 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8678 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 30.68 _reflns_number_total 2606 _reflns_number_gt 2267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0530P)^2^+0.1724P] 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 ? _refine_ls_number_reflns 2606 _refine_ls_number_parameters 219 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.25687(17) 0.52382(9) 0.27090(9) 0.0540(3) Uani 1 1 d . . . C9 C 0.5840(3) 0.69767(14) 0.33977(12) 0.0511(4) Uani 1 1 d . . . C3 C 0.3947(2) 0.72393(12) 0.21331(10) 0.0399(3) Uani 1 1 d . . . C1 C 0.4018(2) 0.56396(12) 0.27505(10) 0.0400(3) Uani 1 1 d . . . C19 C 0.5277(3) 0.42048(14) 0.20911(12) 0.0517(4) Uani 1 1 d . . . H19A H 0.6356 0.3809 0.2084 0.062 Uiso 1 1 calc R . . H19B H 0.4344 0.3836 0.2313 0.062 Uiso 1 1 calc R . . C10 C 0.2485(3) 0.69994(14) 0.33865(12) 0.0526(4) Uani 1 1 d . . . H10A H 0.2466 0.7682 0.3433 0.063 Uiso 1 1 calc R . . H10B H 0.1343 0.6808 0.3089 0.063 Uiso 1 1 calc R . . C2 C 0.4104(2) 0.67153(12) 0.29231(9) 0.0404(3) Uani 1 1 d . . . C11 C 0.5783(2) 0.50677(12) 0.26316(10) 0.0409(3) Uani 1 1 d . . . C12 C 0.6609(3) 0.47282(12) 0.34480(11) 0.0435(4) Uani 1 1 d . . . C8 C 0.2619(3) 0.69618(14) 0.15387(12) 0.0494(4) Uani 1 1 d . . . H8 H 0.1854 0.6453 0.1615 0.059 Uiso 1 1 calc R . . C13 C 0.8476(3) 0.48160(16) 0.36965(13) 0.0561(5) Uani 1 1 d . . . H13 H 0.9256 0.5104 0.3375 0.067 Uiso 1 1 calc R . . C18 C 0.7117(2) 0.56506(14) 0.22613(11) 0.0469(4) Uani 1 1 d . . . C17 C 0.5479(3) 0.42802(16) 0.39316(13) 0.0567(5) Uani 1 1 d . . . H17 H 0.4235 0.4203 0.3767 0.068 Uiso 1 1 calc R . . C4 C 0.5021(3) 0.80215(16) 0.20174(14) 0.0584(5) Uani 1 1 d . . . H4 H 0.5906 0.8221 0.2413 0.070 Uiso 1 1 calc R . . C7 C 0.2431(3) 0.74426(17) 0.08309(12) 0.0606(5) Uani 1 1 d . . . H7 H 0.1559 0.7244 0.0430 0.073 Uiso 1 1 calc R . . C6 C 0.3517(4) 0.82073(19) 0.07169(14) 0.0660(6) Uani 1 1 d . . . H6 H 0.3398 0.8520 0.0238 0.079 Uiso 1 1 calc R . . C16 C 0.6201(4) 0.39478(17) 0.46603(15) 0.0720(7) Uani 1 1 d . . . H16 H 0.5435 0.3655 0.4985 0.086 Uiso 1 1 calc R . . C15 C 0.8044(4) 0.40485(19) 0.49063(14) 0.0741(7) Uani 1 1 d . . . H15 H 0.8521 0.3829 0.5397 0.089 Uiso 1 1 calc R . . C5 C 0.4780(4) 0.8510(2) 0.13124(16) 0.0722(7) Uani 1 1 d . . . H5 H 0.5479 0.9046 0.1244 0.087 Uiso 1 1 calc R . . C14 C 0.9169(4) 0.4473(2) 0.44262(15) 0.0722(7) Uani 1 1 d . . . H14 H 1.0417 0.4532 0.4590 0.087 Uiso 1 1 calc R . . N2 N 0.8151(3) 0.60723(17) 0.19541(12) 0.0662(5) Uani 1 1 d . . . N1 N 0.7134(3) 0.72153(16) 0.37714(14) 0.0754(6) Uani 1 1 d . . . C20 C 0.4573(4) 0.4460(2) 0.12565(14) 0.0674(6) Uani 1 1 d . . . H20A H 0.3509 0.4856 0.1256 0.101 Uiso 1 1 calc R . . H20B H 0.4250 0.3894 0.0966 0.101 Uiso 1 1 calc R . . H20C H 0.5515 0.4791 0.1019 0.101 Uiso 1 1 calc R . . C21 C 0.2566(4) 0.65718(18) 0.42011(15) 0.0694(6) Uani 1 1 d . . . H21A H 0.2542 0.5896 0.4162 0.104 Uiso 1 1 calc R . . H21B H 0.1528 0.6783 0.4451 0.104 Uiso 1 1 calc R . . H21C H 0.3680 0.6767 0.4505 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 0.0414(7) 0.0464(7) 0.0754(9) -0.0029(7) 0.0123(6) -0.0021(6) C9 0.0598(11) 0.0463(9) 0.0455(9) -0.0025(8) -0.0018(8) -0.0012(8) C3 0.0414(8) 0.0397(8) 0.0386(8) 0.0000(6) 0.0051(6) 0.0027(7) C1 0.0392(8) 0.0397(7) 0.0418(8) 0.0009(7) 0.0078(6) 0.0018(6) C19 0.0561(10) 0.0474(9) 0.0526(10) -0.0100(8) 0.0107(8) 0.0048(8) C10 0.0644(12) 0.0466(9) 0.0498(10) 0.0003(8) 0.0191(8) 0.0120(9) C2 0.0436(8) 0.0396(7) 0.0377(8) -0.0003(6) 0.0033(6) 0.0030(7) C11 0.0410(8) 0.0410(8) 0.0417(8) 0.0009(7) 0.0093(6) 0.0040(7) C12 0.0507(9) 0.0384(8) 0.0425(9) 0.0017(7) 0.0107(7) 0.0087(7) C8 0.0522(10) 0.0467(9) 0.0478(10) -0.0003(8) -0.0015(8) -0.0027(8) C13 0.0560(11) 0.0568(11) 0.0548(11) 0.0090(9) 0.0024(9) 0.0047(9) C18 0.0422(8) 0.0565(10) 0.0425(8) 0.0048(8) 0.0068(7) 0.0048(8) C17 0.0638(12) 0.0538(11) 0.0561(11) 0.0092(9) 0.0234(9) 0.0111(9) C4 0.0506(11) 0.0592(11) 0.0644(13) 0.0116(10) 0.0015(9) -0.0116(9) C7 0.0718(14) 0.0630(12) 0.0447(10) 0.0003(9) -0.0040(9) 0.0049(11) C6 0.0732(14) 0.0775(15) 0.0494(11) 0.0188(10) 0.0156(10) 0.0103(12) C16 0.105(2) 0.0608(13) 0.0566(12) 0.0130(10) 0.0376(12) 0.0239(13) C15 0.108(2) 0.0684(14) 0.0447(11) 0.0048(10) 0.0053(12) 0.0258(14) C5 0.0650(13) 0.0742(15) 0.0784(16) 0.0262(13) 0.0114(12) -0.0138(12) C14 0.0779(16) 0.0719(15) 0.0620(13) 0.0067(12) -0.0140(11) 0.0111(12) N2 0.0549(10) 0.0867(14) 0.0592(10) 0.0124(10) 0.0160(8) -0.0072(9) N1 0.0783(14) 0.0760(13) 0.0657(12) -0.0068(10) -0.0202(10) -0.0098(11) C20 0.0695(14) 0.0764(15) 0.0549(12) -0.0151(11) 0.0003(10) 0.0064(12) C21 0.0971(18) 0.0624(13) 0.0537(12) 0.0055(10) 0.0309(11) 0.0107(13) _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 1.199(2) . ? C9 N1 1.137(3) . ? C9 C2 1.480(3) . ? C3 C4 1.385(3) . ? C3 C8 1.388(2) . ? C3 C2 1.541(2) . ? C1 C2 1.552(2) . ? C1 C11 1.556(2) . ? C19 C20 1.514(3) . ? C19 C11 1.555(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C10 C21 1.521(3) . ? C10 C2 1.551(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C18 1.474(2) . ? C11 C12 1.543(2) . ? C12 C17 1.388(3) . ? C12 C13 1.392(3) . ? C8 C7 1.388(3) . ? C8 H8 0.9300 . ? C13 C14 1.389(3) . ? C13 H13 0.9300 . ? C18 N2 1.138(3) . ? C17 C16 1.388(4) . ? C17 H17 0.9300 . ? C4 C5 1.390(3) . ? C4 H4 0.9300 . ? C7 C6 1.370(4) . ? C7 H7 0.9300 . ? C6 C5 1.371(4) . ? C6 H6 0.9300 . ? C16 C15 1.376(4) . ? C16 H16 0.9300 . ? C15 C14 1.366(4) . ? C15 H15 0.9300 . ? C5 H5 0.9300 . ? C14 H14 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 N1 C9 C2 176.8(2) . . ? C4 C3 C8 118.92(17) . . ? C4 C3 C2 121.50(16) . . ? C8 C3 C2 119.45(15) . . ? O1 C1 C2 119.60(15) . . ? O1 C1 C11 119.14(15) . . ? C2 C1 C11 121.26(14) . . ? C20 C19 C11 114.41(18) . . ? C20 C19 H19A 108.7 . . ? C11 C19 H19A 108.7 . . ? C20 C19 H19B 108.7 . . ? C11 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C21 C10 C2 114.46(17) . . ? C21 C10 H10A 108.6 . . ? C2 C10 H10A 108.6 . . ? C21 C10 H10B 108.6 . . ? C2 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C9 C2 C3 110.05(15) . . ? C9 C2 C10 108.04(16) . . ? C3 C2 C10 109.87(14) . . ? C9 C2 C1 111.42(14) . . ? C3 C2 C1 107.84(13) . . ? C10 C2 C1 109.61(14) . . ? C18 C11 C12 110.75(15) . . ? C18 C11 C19 107.92(15) . . ? C12 C11 C19 110.07(14) . . ? C18 C11 C1 111.29(14) . . ? C12 C11 C1 106.95(13) . . ? C19 C11 C1 109.87(15) . . ? C17 C12 C13 119.06(19) . . ? C17 C12 C11 119.11(18) . . ? C13 C12 C11 121.74(16) . . ? C7 C8 C3 120.08(19) . . ? C7 C8 H8 120.0 . . ? C3 C8 H8 120.0 . . ? C14 C13 C12 119.8(2) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? N2 C18 C11 177.2(2) . . ? C16 C17 C12 120.1(2) . . ? C16 C17 H17 119.9 . . ? C12 C17 H17 119.9 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C7 C8 120.6(2) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C6 C5 119.7(2) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C15 C16 C17 120.5(2) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C14 C15 C16 119.6(2) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C15 C14 C13 121.0(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C10 C21 H21A 109.5 . . ? C10 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C10 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C4 C3 C2 C9 -16.9(2) . . . . ? C8 C3 C2 C9 167.36(16) . . . . ? C4 C3 C2 C10 101.9(2) . . . . ? C8 C3 C2 C10 -73.8(2) . . . . ? C4 C3 C2 C1 -138.65(18) . . . . ? C8 C3 C2 C1 45.6(2) . . . . ? C21 C10 C2 C9 -56.2(2) . . . . ? C21 C10 C2 C3 -176.26(18) . . . . ? C21 C10 C2 C1 65.4(2) . . . . ? O1 C1 C2 C9 146.10(18) . . . . ? C11 C1 C2 C9 -33.8(2) . . . . ? O1 C1 C2 C3 -93.02(19) . . . . ? C11 C1 C2 C3 87.13(18) . . . . ? O1 C1 C2 C10 26.6(2) . . . . ? C11 C1 C2 C10 -153.28(16) . . . . ? C20 C19 C11 C18 -55.0(2) . . . . ? C20 C19 C11 C12 -175.99(17) . . . . ? C20 C19 C11 C1 66.5(2) . . . . ? O1 C1 C11 C18 147.44(17) . . . . ? C2 C1 C11 C18 -32.7(2) . . . . ? O1 C1 C11 C12 -91.5(2) . . . . ? C2 C1 C11 C12 88.38(18) . . . . ? O1 C1 C11 C19 28.0(2) . . . . ? C2 C1 C11 C19 -152.18(15) . . . . ? C18 C11 C12 C17 171.20(17) . . . . ? C19 C11 C12 C17 -69.5(2) . . . . ? C1 C11 C12 C17 49.8(2) . . . . ? C18 C11 C12 C13 -12.1(2) . . . . ? C19 C11 C12 C13 107.1(2) . . . . ? C1 C11 C12 C13 -133.54(18) . . . . ? C4 C3 C8 C7 2.5(3) . . . . ? C2 C3 C8 C7 178.36(17) . . . . ? C17 C12 C13 C14 -1.2(3) . . . . ? C11 C12 C13 C14 -177.90(19) . . . . ? C13 C12 C17 C16 1.6(3) . . . . ? C11 C12 C17 C16 178.38(18) . . . . ? C8 C3 C4 C5 -0.8(3) . . . . ? C2 C3 C4 C5 -176.5(2) . . . . ? C3 C8 C7 C6 -1.6(3) . . . . ? C8 C7 C6 C5 -1.1(4) . . . . ? C12 C17 C16 C15 -0.8(3) . . . . ? C17 C16 C15 C14 -0.5(4) . . . . ? C7 C6 C5 C4 2.9(4) . . . . ? C3 C4 C5 C6 -1.9(4) . . . . ? C16 C15 C14 C13 0.9(4) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.168 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.028