Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2002 data_pmr4 _database_code_CSD 191119 _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Peter Rentzepis' 'Yongchao Liang' _publ_contact_author_name 'Prof Peter Rentzepis' _publ_contact_author_address ; University of California, Irvine Departmentof Chemistry Irvine California 92697 UNITED STATES OF AMERICA ; _publ_contact_author_email 'PMRENTZE@UCI.EDU' _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; New Near Infrared Sensitive Photochromic Fluorescing Molecules ; _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H17 N3 O2' _chemical_formula_weight 343.38 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 8.9150(5) _cell_length_b 10.6693(7) _cell_length_c 11.0624(7) _cell_angle_alpha 107.4560(10) _cell_angle_beta 97.5000(10) _cell_angle_gamma 114.0340(10) _cell_volume 877.33(9) _cell_formula_units_Z 2 _cell_measurement_temperature 158(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular_plate _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9764 _exptl_absorpt_correction_T_max 0.9957 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 158(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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_% '< 1.0' _diffrn_reflns_number 9579 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.26 _reflns_number_total 4176 _reflns_number_gt 2615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART/SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0572P)^2^+0.4007P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXTL _refine_ls_extinction_coef 0.009(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4176 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1446 _refine_ls_wR_factor_gt 0.1169 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 0.31083(19) 0.88696(17) 0.01758(14) 0.0337(4) Uani 1 1 d . . . O2 O 0.3291(2) 0.73143(18) 0.11082(16) 0.0438(4) Uani 1 1 d . . . N1 N 0.2490(2) 1.37003(19) 0.41855(17) 0.0292(4) Uani 1 1 d . . . N2 N 0.1638(3) 1.2578(2) -0.0229(2) 0.0469(5) Uani 1 1 d . . . N3 N 0.2899(3) 0.9307(3) -0.2774(2) 0.0542(6) Uani 1 1 d . . . C1 C 0.2918(3) 1.4365(2) 0.5539(2) 0.0280(5) Uani 1 1 d . . . C2 C 0.2706(3) 1.5545(2) 0.6344(2) 0.0359(5) Uani 1 1 d . . . C3 C 0.3261(3) 1.5971(3) 0.7695(3) 0.0425(6) Uani 1 1 d . . . C4 C 0.3997(3) 1.5263(3) 0.8250(3) 0.0430(6) Uani 1 1 d . . . C5 C 0.4237(3) 1.4125(3) 0.7473(2) 0.0364(5) Uani 1 1 d . . . C6 C 0.3687(2) 1.3654(2) 0.6087(2) 0.0278(5) Uani 1 1 d . . . C7 C 0.3717(2) 1.2531(2) 0.5017(2) 0.0249(4) Uani 1 1 d . . . C8 C 0.2958(2) 1.2571(2) 0.3860(2) 0.0253(4) Uani 1 1 d . . . C9 C 0.2767(3) 1.1810(2) 0.2495(2) 0.0263(4) Uani 1 1 d . . . C10 C 0.2575(2) 1.0434(2) 0.18055(19) 0.0247(4) Uani 1 1 d . . . C11 C 0.2759(3) 1.0035(2) 0.0473(2) 0.0271(4) Uani 1 1 d . . . C12 C 0.2949(3) 0.8297(2) 0.1192(2) 0.0314(5) Uani 1 1 d . . . C13 C 0.2325(2) 0.9134(2) 0.21288(19) 0.0251(4) Uani 1 1 d . . . C14 C 0.1319(3) 0.8522(2) 0.2824(2) 0.0295(5) Uani 1 1 d . . . C15 C 0.0974(4) 0.7054(3) 0.2891(3) 0.0432(6) Uani 1 1 d . . . C16 C 0.0361(3) 0.9219(3) 0.3522(2) 0.0359(5) Uani 1 1 d . . . C17 C 0.1589(3) 1.4062(3) 0.3255(3) 0.0369(5) Uani 1 1 d . . . C18 C 0.4602(3) 1.1636(3) 0.5148(2) 0.0336(5) Uani 1 1 d . . . C19 C 0.2583(3) 1.0552(2) -0.0494(2) 0.0308(5) Uani 1 1 d . . . C20 C 0.2078(3) 1.1686(3) -0.0344(2) 0.0337(5) Uani 1 1 d . . . C21 C 0.2778(3) 0.9871(3) -0.1759(2) 0.0385(5) Uani 1 1 d . . . H2 H 0.221(3) 1.605(3) 0.592(2) 0.044(7) Uiso 1 1 d . . . H3 H 0.312(3) 1.678(3) 0.826(3) 0.050(7) Uiso 1 1 d . . . H4 H 0.431(3) 1.559(3) 0.922(3) 0.051(7) Uiso 1 1 d . . . H5 H 0.476(3) 1.362(3) 0.785(2) 0.045(7) Uiso 1 1 d . . . H9 H 0.281(3) 1.239(2) 0.198(2) 0.029(6) Uiso 1 1 d . . . H15A H -0.024(5) 0.634(4) 0.237(3) 0.085(10) Uiso 1 1 d . . . H15B H 0.116(4) 0.716(3) 0.385(3) 0.075(10) Uiso 1 1 d . . . H15C H 0.166(3) 0.662(3) 0.249(3) 0.053(8) Uiso 1 1 d . . . H16A H 0.089(4) 0.966(4) 0.454(3) 0.083(10) Uiso 1 1 d . . . H16B H -0.076(4) 0.847(3) 0.335(3) 0.050(7) Uiso 1 1 d . . . H16C H 0.023(3) 0.999(3) 0.322(3) 0.050(7) Uiso 1 1 d . . . H17A H 0.116(4) 1.473(4) 0.373(3) 0.086(10) Uiso 1 1 d . . . H17B H 0.223(4) 1.444(3) 0.269(3) 0.071(9) Uiso 1 1 d . . . H17C H 0.063(4) 1.319(4) 0.264(3) 0.079(10) Uiso 1 1 d . . . H18A H 0.548(4) 1.213(3) 0.602(3) 0.058(8) Uiso 1 1 d . . . H18B H 0.381(4) 1.059(3) 0.509(3) 0.060(8) Uiso 1 1 d . . . H18C H 0.521(4) 1.149(3) 0.445(3) 0.064(8) 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 O1 0.0437(9) 0.0359(9) 0.0292(8) 0.0112(7) 0.0172(7) 0.0247(7) O2 0.0591(11) 0.0380(10) 0.0467(10) 0.0148(8) 0.0188(8) 0.0342(9) N1 0.0353(10) 0.0244(9) 0.0318(10) 0.0105(8) 0.0134(8) 0.0170(8) N2 0.0542(13) 0.0427(12) 0.0375(12) 0.0131(10) -0.0015(10) 0.0234(11) N3 0.0676(15) 0.0666(16) 0.0355(12) 0.0203(11) 0.0248(11) 0.0349(13) C1 0.0271(10) 0.0199(10) 0.0327(12) 0.0073(9) 0.0142(9) 0.0076(8) C2 0.0352(12) 0.0227(11) 0.0462(14) 0.0085(10) 0.0201(10) 0.0116(9) C3 0.0393(13) 0.0247(12) 0.0441(15) -0.0027(11) 0.0200(11) 0.0066(10) C4 0.0378(13) 0.0377(14) 0.0303(13) -0.0003(11) 0.0123(10) 0.0059(11) C5 0.0315(12) 0.0352(13) 0.0301(12) 0.0072(10) 0.0088(9) 0.0087(10) C6 0.0252(10) 0.0206(10) 0.0289(11) 0.0053(8) 0.0103(8) 0.0053(8) C7 0.0242(10) 0.0197(10) 0.0276(11) 0.0072(8) 0.0082(8) 0.0088(8) C8 0.0267(10) 0.0186(10) 0.0294(11) 0.0078(8) 0.0106(8) 0.0100(8) C9 0.0290(10) 0.0268(11) 0.0261(11) 0.0116(9) 0.0100(8) 0.0144(9) C10 0.0231(9) 0.0267(11) 0.0240(10) 0.0094(9) 0.0083(8) 0.0113(8) C11 0.0268(10) 0.0237(10) 0.0276(11) 0.0068(9) 0.0093(8) 0.0109(8) C12 0.0345(11) 0.0288(12) 0.0311(12) 0.0100(9) 0.0090(9) 0.0165(10) C13 0.0264(10) 0.0232(10) 0.0229(10) 0.0063(8) 0.0060(8) 0.0113(8) C14 0.0271(10) 0.0267(11) 0.0290(11) 0.0099(9) 0.0046(8) 0.0093(9) C15 0.0411(14) 0.0353(14) 0.0566(18) 0.0264(13) 0.0151(13) 0.0149(12) C16 0.0291(12) 0.0414(14) 0.0359(14) 0.0161(11) 0.0150(10) 0.0131(11) C17 0.0427(14) 0.0362(14) 0.0433(14) 0.0191(12) 0.0161(12) 0.0254(12) C18 0.0330(12) 0.0324(13) 0.0328(13) 0.0086(10) 0.0046(10) 0.0173(10) C19 0.0299(11) 0.0331(12) 0.0273(11) 0.0114(9) 0.0104(9) 0.0127(9) C20 0.0348(12) 0.0352(13) 0.0238(11) 0.0111(10) 0.0041(9) 0.0116(10) C21 0.0390(13) 0.0464(14) 0.0316(13) 0.0177(11) 0.0124(10) 0.0193(11) _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 C11 1.359(2) . ? O1 C12 1.429(3) . ? O2 C12 1.187(2) . ? N1 C1 1.373(3) . ? N1 C8 1.394(2) . ? N1 C17 1.459(3) . ? N2 C20 1.149(3) . ? N3 C21 1.147(3) . ? C1 C2 1.407(3) . ? C1 C6 1.416(3) . ? C2 C3 1.378(4) . ? C3 C4 1.399(4) . ? C4 C5 1.375(3) . ? C5 C6 1.408(3) . ? C6 C7 1.422(3) . ? C7 C8 1.388(3) . ? C7 C18 1.490(3) . ? C8 C9 1.433(3) . ? C9 C10 1.362(3) . ? C10 C11 1.457(3) . ? C10 C13 1.472(3) . ? C11 C19 1.361(3) . ? C12 C13 1.477(3) . ? C13 C14 1.351(3) . ? C14 C16 1.491(3) . ? C14 C15 1.495(3) . ? C19 C20 1.427(3) . ? C19 C21 1.440(3) . ? 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 C11 O1 C12 109.81(15) . . ? C1 N1 C8 108.68(17) . . ? C1 N1 C17 125.00(18) . . ? C8 N1 C17 126.21(18) . . ? N1 C1 C2 130.3(2) . . ? N1 C1 C6 107.97(17) . . ? C2 C1 C6 121.7(2) . . ? C3 C2 C1 117.1(2) . . ? C2 C3 C4 121.8(2) . . ? C5 C4 C3 121.5(2) . . ? C4 C5 C6 118.6(2) . . ? C5 C6 C1 119.30(19) . . ? C5 C6 C7 133.3(2) . . ? C1 C6 C7 107.45(18) . . ? C8 C7 C6 106.81(17) . . ? C8 C7 C18 127.56(19) . . ? C6 C7 C18 125.22(19) . . ? C7 C8 N1 109.08(17) . . ? C7 C8 C9 132.23(18) . . ? N1 C8 C9 118.28(18) . . ? C10 C9 C8 132.3(2) . . ? C9 C10 C11 121.12(19) . . ? C9 C10 C13 134.16(19) . . ? C11 C10 C13 104.51(16) . . ? O1 C11 C19 116.97(18) . . ? O1 C11 C10 110.00(17) . . ? C19 C11 C10 132.96(19) . . ? O2 C12 O1 118.07(19) . . ? O2 C12 C13 135.4(2) . . ? O1 C12 C13 106.54(16) . . ? C14 C13 C10 129.63(18) . . ? C14 C13 C12 122.23(19) . . ? C10 C13 C12 105.64(17) . . ? C13 C14 C16 122.2(2) . . ? C13 C14 C15 123.6(2) . . ? C16 C14 C15 114.1(2) . . ? C11 C19 C20 122.36(19) . . ? C11 C19 C21 119.9(2) . . ? C20 C19 C21 117.5(2) . . ? N2 C20 C19 178.7(2) . . ? N3 C21 C19 178.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 C2 -179.9(2) . . . . ? C17 N1 C1 C2 -3.7(3) . . . . ? C8 N1 C1 C6 0.5(2) . . . . ? C17 N1 C1 C6 176.7(2) . . . . ? N1 C1 C2 C3 179.6(2) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 1.5(4) . . . . ? C3 C4 C5 C6 -1.5(3) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C4 C5 C6 C7 -179.3(2) . . . . ? N1 C1 C6 C5 -179.55(18) . . . . ? C2 C1 C6 C5 0.8(3) . . . . ? N1 C1 C6 C7 0.1(2) . . . . ? C2 C1 C6 C7 -179.50(18) . . . . ? C5 C6 C7 C8 178.9(2) . . . . ? C1 C6 C7 C8 -0.7(2) . . . . ? C5 C6 C7 C18 -8.0(4) . . . . ? C1 C6 C7 C18 172.3(2) . . . . ? C6 C7 C8 N1 1.1(2) . . . . ? C18 C7 C8 N1 -171.8(2) . . . . ? C6 C7 C8 C9 173.4(2) . . . . ? C18 C7 C8 C9 0.6(4) . . . . ? C1 N1 C8 C7 -1.0(2) . . . . ? C17 N1 C8 C7 -177.1(2) . . . . ? C1 N1 C8 C9 -174.60(17) . . . . ? C17 N1 C8 C9 9.3(3) . . . . ? C7 C8 C9 C10 32.1(4) . . . . ? N1 C8 C9 C10 -156.1(2) . . . . ? C8 C9 C10 C11 -167.2(2) . . . . ? C8 C9 C10 C13 6.8(4) . . . . ? C12 O1 C11 C19 -169.68(18) . . . . ? C12 O1 C11 C10 7.8(2) . . . . ? C9 C10 C11 O1 158.85(18) . . . . ? C13 C10 C11 O1 -16.7(2) . . . . ? C9 C10 C11 C19 -24.2(3) . . . . ? C13 C10 C11 C19 160.3(2) . . . . ? C11 O1 C12 O2 -176.62(19) . . . . ? C11 O1 C12 C13 4.4(2) . . . . ? C9 C10 C13 C14 41.9(4) . . . . ? C11 C10 C13 C14 -143.4(2) . . . . ? C9 C10 C13 C12 -156.1(2) . . . . ? C11 C10 C13 C12 18.6(2) . . . . ? O2 C12 C13 C14 -29.6(4) . . . . ? O1 C12 C13 C14 149.14(19) . . . . ? O2 C12 C13 C10 166.8(3) . . . . ? O1 C12 C13 C10 -14.5(2) . . . . ? C10 C13 C14 C16 -6.2(3) . . . . ? C12 C13 C14 C16 -165.5(2) . . . . ? C10 C13 C14 C15 169.7(2) . . . . ? C12 C13 C14 C15 10.3(3) . . . . ? O1 C11 C19 C20 174.73(18) . . . . ? C10 C11 C19 C20 -2.0(4) . . . . ? O1 C11 C19 C21 -0.4(3) . . . . ? C10 C11 C19 C21 -177.1(2) . . . . ? C11 C19 C20 N2 -81(10) . . . . ? C21 C19 C20 N2 94(10) . . . . ? C11 C19 C21 N3 82(12) . . . . ? C20 C19 C21 N3 -94(12) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.273 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.050