# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name 'Vladimir Khodorkovsky' 'Vladimir A. Lokshin' 'Anatoly Metelitsa' 'Gerard Pepe' 'Andre Samat' 'Magali Vales' _publ_contact_author_name 'Prof Vladimir Khodorkovsky' _publ_contact_author_address ; Department of Chemistry Ben Gurion University POB 653 Beer Sheva 84105 ISRAEL ; _publ_contact_author_email HODOR@BGUMAIL.BGU.AC.IL _publ_section_title ; A novel photoreversible photochromic system involving hydrogen transfer/cyclization sequence ; data_vla281 _database_code_CSD 197132 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H21 N O2' _chemical_formula_weight 367.43 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.382(1) _cell_length_b 28.831(4) _cell_length_c 9.248(1) _cell_angle_alpha 90.00 _cell_angle_beta 97.670(1) _cell_angle_gamma 90.00 _cell_volume 1950.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'pseudo hexagonal platelets' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _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 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2253 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.3291 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 32.89 _reflns_number_total 2253 _reflns_number_gt 952 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0450P)^2^] 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 SHELXL _refine_ls_extinction_coef 0.38(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2253 _refine_ls_number_parameters 338 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0934 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.3623 _refine_ls_wR_factor_gt 0.1645 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 C1 C 0.2930(4) 0.11336(12) 0.2706(3) 0.0374(9) Uani 1 1 d . . . C2 C 0.4387(5) 0.10934(14) 0.3845(4) 0.0497(10) Uani 1 1 d . . . C3 C 0.4329(6) 0.13084(17) 0.5157(4) 0.0629(12) Uani 1 1 d . . . C4 C 0.2816(6) 0.15702(17) 0.5341(4) 0.0632(12) Uani 1 1 d . . . C5 C 0.1337(5) 0.16106(14) 0.4256(4) 0.0516(10) Uani 1 1 d . . . C6 C 0.1334(4) 0.13858(12) 0.2905(3) 0.0363(8) Uani 1 1 d . . . N7 N -0.0135(3) 0.14112(10) 0.1804(3) 0.0367(7) Uani 1 1 d . . . C8 C -0.0235(4) 0.10626(11) 0.0605(3) 0.0320(7) Uani 1 1 d . . . C9 C 0.1645(4) 0.10676(12) 0.0082(3) 0.0323(7) Uani 1 1 d . . . C10 C 0.3136(4) 0.09320(12) 0.1280(4) 0.0387(8) Uani 1 1 d . . . C11 C -0.1832(6) 0.16150(19) 0.2164(5) 0.0636(12) Uani 1 1 d . . . C12 C -0.0711(5) 0.05845(13) 0.1187(4) 0.0409(8) Uani 1 1 d . . . O13 O 0.4426(3) 0.06948(10) 0.1051(3) 0.0572(8) Uani 1 1 d . . . C14 C -0.1675(4) 0.12092(10) -0.0698(3) 0.0315(8) Uani 1 1 d . . . C15 C -0.1239(4) 0.16836(11) -0.1258(3) 0.0337(7) Uani 1 1 d . . . C16 C 0.0555(4) 0.18424(10) -0.1157(3) 0.0356(8) Uani 1 1 d . . . C17 C 0.2092(4) 0.15477(12) -0.0479(3) 0.0366(8) Uani 1 1 d . . . O18 O 0.3670(3) 0.16760(11) -0.0380(3) 0.0630(8) Uani 1 1 d . . . C19 C -0.2631(5) 0.19673(12) -0.1927(4) 0.0430(9) Uani 1 1 d . . . C20 C -0.2239(6) 0.23919(13) -0.2492(5) 0.0574(11) Uani 1 1 d . . . C21 C -0.0451(6) 0.25456(16) -0.2393(6) 0.0660(12) Uani 1 1 d . . . C22 C 0.0943(5) 0.22733(14) -0.1711(4) 0.0536(10) Uani 1 1 d . . . C23 C -0.1903(4) 0.08547(11) -0.1932(3) 0.0361(8) Uani 1 1 d . . . C24 C -0.3239(5) 0.05139(13) -0.1962(4) 0.0482(9) Uani 1 1 d . . . C25 C -0.3490(6) 0.01936(15) -0.3091(5) 0.0626(12) Uani 1 1 d . . . C26 C -0.2454(6) 0.02096(18) -0.4187(5) 0.0677(13) Uani 1 1 d . . . C27 C -0.1130(6) 0.05458(18) -0.4194(4) 0.0621(12) Uani 1 1 d . . . C28 C -0.0864(5) 0.08697(14) -0.3075(4) 0.0460(9) Uani 1 1 d . . . H29 H 0.552(6) 0.0917(15) 0.367(4) 0.064(12) Uiso 1 1 d . . . H30 H 0.539(7) 0.1269(19) 0.605(6) 0.093(16) Uiso 1 1 d . . . H31 H 0.271(6) 0.1703(18) 0.631(6) 0.079(13) Uiso 1 1 d . . . H32 H 0.034(5) 0.1782(15) 0.449(4) 0.053(11) Uiso 1 1 d . . . H33 H 0.168(4) 0.0848(11) -0.078(3) 0.029(8) Uiso 1 1 d . . . H34 H -0.134(11) 0.200(3) 0.237(8) 0.14(2) Uiso 1 1 d . . . H35 H -0.289(7) 0.164(2) 0.131(6) 0.088(15) Uiso 1 1 d . . . H36 H -0.231(9) 0.154(3) 0.315(8) 0.13(2) Uiso 1 1 d . . . H37 H 0.018(6) 0.0491(15) 0.203(4) 0.061(11) Uiso 1 1 d . . . H38 H -0.193(6) 0.0556(15) 0.148(4) 0.059(11) Uiso 1 1 d . . . H39 H -0.060(6) 0.033(2) 0.043(5) 0.084(14) Uiso 1 1 d . . . H40 H -0.288(5) 0.1224(10) -0.042(3) 0.030(8) Uiso 1 1 d . . . H41 H -0.404(5) 0.1844(12) -0.203(4) 0.043(9) Uiso 1 1 d . . . H42 H -0.317(6) 0.2543(13) -0.303(4) 0.047(11) Uiso 1 1 d . . . H43 H -0.014(7) 0.284(2) -0.272(5) 0.082(13) Uiso 1 1 d . . . H44 H 0.212(6) 0.2385(14) -0.163(4) 0.050(11) Uiso 1 1 d . . . H45 H -0.404(4) 0.0528(13) -0.112(4) 0.039(8) Uiso 1 1 d . . . H46 H -0.443(7) -0.0028(19) -0.307(6) 0.088(15) Uiso 1 1 d . . . H47 H -0.259(6) -0.001(2) -0.494(6) 0.090(15) Uiso 1 1 d . . . H48 H -0.047(6) 0.0571(17) -0.483(5) 0.061(13) Uiso 1 1 d . . . H49 H 0.002(5) 0.1102(14) -0.310(4) 0.041(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(2) 0.0415(18) 0.0339(18) 0.0025(15) 0.0007(13) -0.0047(14) C2 0.044(2) 0.054(2) 0.047(2) 0.0048(18) -0.0074(16) -0.0040(16) C3 0.061(3) 0.080(3) 0.042(2) 0.002(2) -0.0129(19) -0.009(2) C4 0.074(3) 0.082(3) 0.032(2) -0.013(2) 0.0023(17) -0.014(2) C5 0.059(3) 0.058(3) 0.039(2) -0.0082(17) 0.0119(16) -0.0057(18) C6 0.0387(17) 0.0393(19) 0.0310(17) 0.0022(13) 0.0050(11) -0.0075(14) N7 0.0348(13) 0.0408(16) 0.0348(15) -0.0071(12) 0.0054(10) 0.0034(11) C8 0.0326(17) 0.0315(15) 0.0319(17) -0.0020(12) 0.0035(12) -0.0002(12) C9 0.0269(17) 0.0386(16) 0.0315(17) -0.0045(14) 0.0045(11) 0.0022(12) C10 0.0301(19) 0.0397(18) 0.047(2) 0.0014(14) 0.0059(13) 0.0019(12) C11 0.044(2) 0.088(4) 0.059(2) -0.025(2) 0.0084(19) 0.019(2) C12 0.037(2) 0.0383(18) 0.047(2) 0.0066(17) 0.0022(15) -0.0041(13) O13 0.0392(14) 0.0700(18) 0.0621(16) -0.0025(14) 0.0056(10) 0.0206(12) C14 0.0245(18) 0.0309(16) 0.0390(18) 0.0002(12) 0.0044(13) -0.0016(10) C15 0.0354(18) 0.0316(16) 0.0345(16) -0.0042(13) 0.0065(11) -0.0009(12) C16 0.0326(18) 0.0343(17) 0.0403(18) -0.0002(14) 0.0068(12) -0.0030(11) C17 0.0270(19) 0.0471(19) 0.0368(17) -0.0020(14) 0.0083(11) -0.0042(13) O18 0.0334(15) 0.077(2) 0.0791(19) 0.0247(16) 0.0078(11) -0.0099(12) C19 0.0384(19) 0.0401(18) 0.050(2) 0.0028(15) 0.0033(14) 0.0004(14) C20 0.055(3) 0.044(2) 0.070(3) 0.0114(19) -0.0009(19) 0.0084(18) C21 0.068(3) 0.039(2) 0.092(3) 0.021(2) 0.013(2) -0.0030(17) C22 0.049(2) 0.042(2) 0.070(3) 0.0085(18) 0.0095(17) -0.0105(16) C23 0.0367(18) 0.0338(17) 0.0350(18) 0.0013(13) -0.0054(13) 0.0002(12) C24 0.051(2) 0.041(2) 0.048(2) 0.0028(17) -0.0110(16) -0.0098(14) C25 0.069(3) 0.042(2) 0.069(3) -0.002(2) -0.022(2) -0.0077(19) C26 0.080(3) 0.057(2) 0.058(3) -0.021(2) -0.022(2) 0.014(2) C27 0.067(3) 0.075(3) 0.043(2) -0.013(2) 0.002(2) 0.012(2) C28 0.048(2) 0.049(2) 0.040(2) -0.0066(16) 0.0022(14) -0.0009(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 C1 C2 1.406(5) . ? C1 C6 1.417(5) . ? C1 C10 1.468(5) . ? C2 C3 1.368(6) . ? C3 C4 1.377(7) . ? C4 C5 1.386(6) . ? C5 C6 1.407(5) . ? C6 N7 1.387(4) . ? N7 C11 1.461(4) . ? N7 C8 1.491(4) . ? C8 C9 1.529(5) . ? C8 C12 1.537(5) . ? C8 C14 1.556(4) . ? C9 C10 1.505(5) . ? C9 C17 1.530(5) . ? C10 O13 1.213(4) . ? C14 C15 1.512(4) . ? C14 C23 1.525(4) . ? C15 C16 1.392(4) . ? C15 C19 1.392(5) . ? C16 C22 1.388(5) . ? C16 C17 1.487(4) . ? C17 O18 1.214(4) . ? C19 C20 1.377(5) . ? C20 C21 1.383(6) . ? C21 C22 1.378(6) . ? C23 C28 1.386(5) . ? C23 C24 1.390(5) . ? C24 C25 1.388(6) . ? C25 C26 1.350(7) . ? C26 C27 1.377(7) . ? C27 C28 1.389(6) . ? 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 C2 C1 C6 120.8(3) . . ? C2 C1 C10 118.6(3) . . ? C6 C1 C10 120.5(3) . . ? C3 C2 C1 121.0(4) . . ? C2 C3 C4 118.7(3) . . ? C3 C4 C5 122.0(4) . . ? C4 C5 C6 120.8(4) . . ? N7 C6 C5 122.4(3) . . ? N7 C6 C1 120.9(3) . . ? C5 C6 C1 116.7(3) . . ? C6 N7 C11 117.7(3) . . ? C6 N7 C8 117.8(3) . . ? C11 N7 C8 118.8(3) . . ? N7 C8 C9 105.8(2) . . ? N7 C8 C12 109.6(3) . . ? C9 C8 C12 112.2(3) . . ? N7 C8 C14 110.7(2) . . ? C9 C8 C14 107.9(2) . . ? C12 C8 C14 110.5(2) . . ? C10 C9 C8 111.7(2) . . ? C10 C9 C17 108.4(2) . . ? C8 C9 C17 111.2(3) . . ? O13 C10 C1 123.9(3) . . ? O13 C10 C9 122.1(3) . . ? C1 C10 C9 113.9(3) . . ? C15 C14 C23 110.9(2) . . ? C15 C14 C8 110.9(2) . . ? C23 C14 C8 113.2(2) . . ? C16 C15 C19 118.4(3) . . ? C16 C15 C14 121.2(3) . . ? C19 C15 C14 120.3(3) . . ? C22 C16 C15 120.7(3) . . ? C22 C16 C17 118.9(3) . . ? C15 C16 C17 120.4(3) . . ? O18 C17 C16 121.9(3) . . ? O18 C17 C9 119.9(3) . . ? C16 C17 C9 118.2(3) . . ? C20 C19 C15 120.7(3) . . ? C19 C20 C21 120.4(4) . . ? C22 C21 C20 119.7(4) . . ? C21 C22 C16 120.0(4) . . ? C28 C23 C24 118.1(3) . . ? C28 C23 C14 122.2(3) . . ? C24 C23 C14 119.7(3) . . ? C25 C24 C23 120.6(4) . . ? C26 C25 C24 120.7(4) . . ? C25 C26 C27 120.1(4) . . ? C26 C27 C28 120.0(4) . . ? C23 C28 C27 120.6(4) . . ? _diffrn_measured_fraction_theta_max 0.165 _diffrn_reflns_theta_full 32.89 _diffrn_measured_fraction_theta_full 0.165 _refine_diff_density_max 0.200 _refine_diff_density_min -0.127 _refine_diff_density_rms 0.031