# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _audit_creation_date 'Fri Apr 19 07:18:46 2002' _audit_creation_method 'by teXsan' _audit_update_record ? #---------------------------------------------------------------- _journal_coden_Cambridge 207 loop_ _publ_author_name 'Yagi, Shigeyuki' 'Fujie, Yoshihiko' 'Hirose, Msahiko' 'Hyodo, Yutaka' 'Murayama, Shin' 'Nakazumi, Hiroyuki' # SUBMISSION DETAILS _publ_contact_author_name 'Dr Shigeyuki Yagi' _publ_contact_author_address ; Department of Applied Materials Science, Graduate School of Engineering Osaka Prefecture University 1-1 Gakuen-cho, Sakai Osaka 599-8531 Japan ; _publ_contact_author_email ' yagi@ams.osakafu-u.ac.jp ' _publ_contact_author_fax ' +81-72-254-9913 ' _publ_contact_author_phone ' +81-72-254-9324 ' _publ_contact_letter ; ? ; _publ_requested_journal ' J. Chem.Soc. Perkin Trans. I, Commun' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #---------------------------------------------------------------- # TITLE AND AUTHOR LIST _publ_section_title ; Synthesis of novel fluorescent bisquaraine dyes with largely extended ?- conjugation systems ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (1999). teXsan. Single Crystal Structure Analysis Software. Version 1.10. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. ; _publ_section_exptl_refinement ; For the refinement, the TEXSAN program was used, and all non-hydrogen atoms were refined using anisotropic thermal parameters. ; #---------------------------------------------------------------- data_afc5r.xtl_master_file _database_code_CSD 184342 #---------------------------------------------------------------- # CHEMICAL DATA _chemical_formula_sum 'C44 H44 N2 O4 ' _chemical_formula_moiety 'C44 H44 N2 O4 ' _chemical_formula_weight 664.84 _chemical_melting_point '280-281 degree' #---------------------------------------------------------------- # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 8.277(6) _cell_length_b 18.29(6) _cell_length_c 12.121(10) _cell_angle_alpha 90 _cell_angle_beta 106.71(7) _cell_angle_gamma 90 _cell_volume 1757(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6 _cell_measurement_theta_min 11.5 _cell_measurement_theta_max 12.4 _cell_measurement_temperature 296.2 #---------------------------------------------------------------- _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none #---------------------------------------------------------------- # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 2970 _diffrn_reflns_av_R_equivalents 0.164 _diffrn_reflns_theta_max 25.01 _diffrn_measured_fraction_theta_max 0.8245 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.8245 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.22 #---------------------------------------------------------------- # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2553 _reflns_number_gt 1145 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1731 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2549 _refine_ls_number_parameters 226 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0003 _refine_diff_density_max 0.59 _refine_diff_density_min -0.47 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #---------------------------------------------------------------- # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.1726(4) -0.2048(2) 1.1999(3) 0.063(1) Uani 1.00 d . . . O2 O 1.4100(4) 0.0139(2) 1.3328(3) 0.064(1) Uani 1.00 d . . . N1 N 1.6629(4) -0.2209(2) 1.5863(3) 0.044(1) Uani 1.00 d . . . C1 C 1.5353(5) -0.2117(2) 1.4908(4) 0.043(1) Uani 1.00 d . . . C2 C 1.4528(5) -0.2854(2) 1.4507(4) 0.043(1) Uani 1.00 d . . . C3 C 1.5504(6) -0.3352(2) 1.5480(4) 0.047(1) Uani 1.00 d . . . C4 C 1.5340(6) -0.4082(3) 1.5676(4) 0.058(2) Uani 1.00 d . . . C5 C 1.6472(7) -0.4399(3) 1.6636(5) 0.065(2) Uani 1.00 d . . . C6 C 1.7728(7) -0.3990(3) 1.7365(4) 0.064(2) Uani 1.00 d . . . C7 C 1.7904(6) -0.3257(3) 1.7191(4) 0.055(2) Uani 1.00 d . . . C8 C 1.6762(5) -0.2951(2) 1.6239(4) 0.043(1) Uani 1.00 d . . . C9 C 1.4945(5) -0.1425(2) 1.4398(4) 0.045(1) Uani 1.00 d . . . C10 C 1.3754(5) -0.1212(2) 1.3419(4) 0.043(1) Uani 1.00 d . . . C11 C 1.2357(5) -0.1456(3) 1.2369(4) 0.048(2) Uani 1.00 d . . . C12 C 1.2116(5) -0.0707(2) 1.1981(4) 0.043(1) Uani 1.00 d . . . C13 C 1.3432(6) -0.0453(3) 1.2970(4) 0.049(2) Uani 1.00 d . . . C14 C 1.1040(5) -0.0353(2) 1.0982(4) 0.043(1) Uani 1.00 d . . . C15 C 0.9780(6) -0.0743(2) 1.0157(4) 0.049(1) Uani 1.00 d . . . C16 C 1.1222(5) 0.0394(2) 1.0803(4) 0.049(1) Uani 1.00 d . . . C17 C 1.4856(6) -0.3075(3) 1.3371(4) 0.061(2) Uani 1.00 d . . . C18 C 1.2639(6) -0.2862(2) 1.4430(4) 0.058(2) Uani 1.00 d . . . C19 C 1.7844(6) -0.1647(2) 1.6426(4) 0.048(1) Uani 1.00 d . . . C20 C 1.9173(6) -0.1521(3) 1.5808(4) 0.056(2) Uani 1.00 d . . . C21 C 2.0437(6) -0.0935(3) 1.6356(5) 0.071(2) Uani 1.00 d . . . C22 C 2.1745(7) -0.0813(3) 1.5738(5) 0.085(2) Uani 1.00 d . . . H4 H 1.4475 -0.4365 1.5171 0.0695 Uiso 1.00 calc . . . H5 H 1.6376 -0.4905 1.6788 0.0780 Uiso 1.00 calc . . . H6 H 1.8494 -0.4222 1.8006 0.0763 Uiso 1.00 calc . . . H7 H 1.8766 -0.2974 1.7699 0.0657 Uiso 1.00 calc . . . H9 H 1.5619 -0.1038 1.4809 0.0534 Uiso 1.00 calc . . . H15 H 0.9624 -0.1249 1.0265 0.0587 Uiso 1.00 calc . . . H16 H 1.2053 0.0666 1.1354 0.0585 Uiso 1.00 calc . . . H171 H 1.4342 -0.3534 1.3127 0.0734 Uiso 1.00 calc . . . H172 H 1.6037 -0.3111 1.3481 0.0734 Uiso 1.00 calc . . . H173 H 1.4393 -0.2716 1.2801 0.0734 Uiso 1.00 calc . . . H181 H 1.2492 -0.2695 1.5137 0.0698 Uiso 1.00 calc . . . H182 H 1.2215 -0.3346 1.4282 0.0698 Uiso 1.00 calc . . . H183 H 1.2043 -0.2549 1.3822 0.0698 Uiso 1.00 calc . . . H191 H 1.7257 -0.1202 1.6436 0.0577 Uiso 1.00 calc . . . H192 H 1.8386 -0.1797 1.7194 0.0577 Uiso 1.00 calc . . . H201 H 1.9764 -0.1966 1.5808 0.0674 Uiso 1.00 calc . . . H202 H 1.8622 -0.1381 1.5037 0.0674 Uiso 1.00 calc . . . H211 H 1.9847 -0.0489 1.6356 0.0857 Uiso 1.00 calc . . . H212 H 2.0990 -0.1075 1.7127 0.0857 Uiso 1.00 calc . . . H221 H 2.2351 -0.1254 1.5736 0.1015 Uiso 1.00 calc . . . H222 H 2.2503 -0.0442 1.6120 0.1015 Uiso 1.00 calc . . . H223 H 2.1210 -0.0667 1.4967 0.1015 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.072(2) 0.047(2) 0.053(2) -0.009(2) -0.008(2) 0.000(2) O2 0.063(2) 0.037(2) 0.071(2) 0.002(2) -0.013(2) -0.008(2) N1 0.042(2) 0.040(2) 0.042(2) 0.000(2) -0.001(2) 0.003(2) C1 0.036(3) 0.046(3) 0.042(3) -0.002(2) 0.003(2) 0.002(2) C2 0.048(3) 0.039(3) 0.038(3) -0.006(2) 0.007(2) -0.003(2) C3 0.051(3) 0.039(3) 0.051(3) 0.002(2) 0.014(3) 0.002(2) C4 0.071(4) 0.036(3) 0.061(4) -0.004(3) 0.009(3) -0.003(2) C5 0.080(4) 0.044(3) 0.071(4) 0.013(3) 0.020(3) 0.019(3) C6 0.071(4) 0.059(4) 0.054(3) 0.020(3) 0.007(3) 0.013(3) C7 0.059(3) 0.047(3) 0.051(3) 0.008(2) 0.003(3) 0.009(3) C8 0.044(3) 0.038(3) 0.043(3) 0.004(2) 0.009(2) 0.006(2) C9 0.037(3) 0.036(3) 0.054(3) 0.002(2) 0.004(2) 0.002(2) C10 0.045(3) 0.039(3) 0.041(3) 0.001(2) 0.004(2) 0.001(2) C11 0.045(3) 0.045(3) 0.047(3) 0.000(2) 0.001(2) -0.001(2) C12 0.044(3) 0.036(3) 0.043(3) 0.001(2) 0.005(2) 0.000(2) C13 0.047(3) 0.046(3) 0.050(3) 0.003(3) 0.005(2) -0.001(2) C14 0.036(3) 0.044(3) 0.044(3) 0.008(2) 0.005(2) 0.009(2) C15 0.046(3) 0.048(3) 0.044(3) -0.002(2) -0.001(3) 0.004(2) C16 0.046(3) 0.041(3) 0.050(3) -0.003(2) -0.001(2) 0.002(2) C17 0.069(4) 0.051(3) 0.058(3) -0.002(3) 0.010(3) 0.001(3) C18 0.051(3) 0.055(3) 0.061(3) -0.010(3) 0.005(3) 0.011(3) C19 0.044(3) 0.042(3) 0.046(3) -0.004(2) -0.005(2) 0.002(2) C20 0.048(3) 0.055(3) 0.058(3) 0.001(3) 0.003(3) 0.000(3) C21 0.057(4) 0.061(4) 0.085(4) -0.008(3) 0.004(3) -0.008(3) C22 0.067(4) 0.095(5) 0.095(5) -0.023(3) 0.028(4) -0.012(4) #---------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #---------------------------------------------------------------- _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.230(5) . . yes O2 C13 1.236(5) . . yes N1 C1 1.334(5) . . yes N1 C8 1.426(5) . . yes N1 C19 1.462(5) . . yes C1 C2 1.526(5) . . yes C1 C9 1.406(6) . . yes C2 C3 1.525(6) . . yes C2 C17 1.532(7) . . yes C2 C18 1.539(6) . . yes C3 C4 1.371(6) . . yes C3 C8 1.385(6) . . yes C4 C5 1.393(6) . . yes C4 H4 0.946 . . no C5 C6 1.376(7) . . yes C5 H5 0.949 . . no C6 C7 1.373(6) . . yes C6 H6 0.950 . . no C7 C8 1.382(6) . . yes C7 H7 0.953 . . no C9 C10 1.364(6) . . yes C9 H9 0.952 . . no C10 C11 1.520(6) . . yes C10 C13 1.485(6) . . yes C11 C12 1.444(6) . . yes C12 C13 1.445(6) . . yes C12 C14 1.434(6) . . yes C14 C15 1.413(6) . . yes C14 C16 1.399(6) . . yes C15 C16 1.376(6) . 3_757 yes C15 H15 0.975 . . no C16 H16 0.982 . . no C17 H171 0.950 . . no C17 H172 0.952 . . no C17 H173 0.951 . . no C18 H181 0.947 . . no C18 H182 0.950 . . no C18 H183 0.949 . . no C19 C20 1.516(6) . . yes C19 H191 0.953 . . no C19 H192 0.955 . . no C20 C21 1.512(6) . . yes C20 H201 0.950 . . no C20 H202 0.943 . . no C21 C22 1.499(7) . . yes C21 H211 0.953 . . no C21 H212 0.960 . . no C22 H221 0.937 . . no C22 H222 0.954 . . no C22 H223 0.950 . . no #---------------------------------------------------------------- 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C8 111.5(4) . 1_555 1_555 yes C1 N1 C19 125.7(4) . 1_555 1_555 yes C8 N1 C19 122.7(3) . 1_555 1_555 yes N1 C1 C2 109.6(4) . 1_555 1_555 yes N1 C1 C9 121.6(4) . 1_555 1_555 yes C2 C1 C9 128.8(4) . 1_555 1_555 yes C1 C2 C3 101.1(3) . 1_555 1_555 yes C1 C2 C17 109.9(4) . 1_555 1_555 yes C1 C2 C18 112.4(4) . 1_555 1_555 yes C3 C2 C17 110.2(4) . 1_555 1_555 yes C3 C2 C18 110.2(4) . 1_555 1_555 yes C17 C2 C18 112.5(4) . 1_555 1_555 yes C2 C3 C4 131.3(4) . 1_555 1_555 yes C2 C3 C8 109.1(4) . 1_555 1_555 yes C4 C3 C8 119.6(4) . 1_555 1_555 yes C3 C4 C5 118.3(4) . 1_555 1_555 yes C3 C4 H4 121.4 . 1_555 1_555 no C5 C4 H4 120.3 . 1_555 1_555 no C4 C5 C6 120.8(5) . 1_555 1_555 yes C4 C5 H5 120.5 . 1_555 1_555 no C6 C5 H5 118.7 . 1_555 1_555 no C5 C6 C7 121.8(4) . 1_555 1_555 yes C5 C6 H6 119.6 . 1_555 1_555 no C7 C6 H6 118.6 . 1_555 1_555 no C6 C7 C8 116.5(4) . 1_555 1_555 yes C6 C7 H7 121.9 . 1_555 1_555 no C8 C7 H7 121.6 . 1_555 1_555 no N1 C8 C3 108.5(4) . 1_555 1_555 yes N1 C8 C7 128.6(4) . 1_555 1_555 yes C3 C8 C7 122.9(4) . 1_555 1_555 yes C1 C9 C10 131.5(4) . 1_555 1_555 yes C1 C9 H9 114.4 . 1_555 1_555 no C10 C9 H9 114.2 . 1_555 1_555 no C9 C10 C11 146.1(4) . 1_555 1_555 yes C9 C10 C13 126.5(4) . 1_555 1_555 yes C11 C10 C13 87.4(3) . 1_555 1_555 yes O1 C11 C10 134.8(4) . 1_555 1_555 yes O1 C11 C12 135.5(4) . 1_555 1_555 yes C10 C11 C12 89.7(3) . 1_555 1_555 yes C11 C12 C13 91.9(4) . 1_555 1_555 yes C11 C12 C14 134.2(4) . 1_555 1_555 yes C13 C12 C14 133.9(4) . 1_555 1_555 yes O2 C13 C10 132.4(4) . 1_555 1_555 yes O2 C13 C12 136.6(4) . 1_555 1_555 yes C10 C13 C12 91.0(4) . 1_555 1_555 yes C12 C14 C15 121.5(4) . 1_555 1_555 yes C12 C14 C16 120.2(4) . 1_555 1_555 yes C15 C14 C16 118.2(4) . 1_555 1_555 yes C14 C15 C16 120.5(4) . 1_555 3_757 yes C14 C15 H15 116.0 . 1_555 1_555 no C16 C15 H15 123.4 . 3_757 1_555 no C14 C16 C15 121.2(4) . 1_555 3_757 yes C14 C16 H16 115.4 . 1_555 1_555 no C15 C16 H16 123.4 . 3_757 1_555 no C2 C17 H171 109.8 . 1_555 1_555 no C2 C17 H172 109.5 . 1_555 1_555 no C2 C17 H173 109.6 . 1_555 1_555 no H171 C17 H172 109.3 . 1_555 1_555 no H171 C17 H173 109.4 . 1_555 1_555 no H172 C17 H173 109.3 . 1_555 1_555 no C2 C18 H181 109.2 . 1_555 1_555 no C2 C18 H182 109.1 . 1_555 1_555 no C2 C18 H183 109.3 . 1_555 1_555 no H181 C18 H182 109.7 . 1_555 1_555 no H181 C18 H183 109.8 . 1_555 1_555 no H182 C18 H183 109.6 . 1_555 1_555 no N1 C19 C20 112.1(4) . 1_555 1_555 yes N1 C19 H191 108.9 . 1_555 1_555 no N1 C19 H192 109.1 . 1_555 1_555 no C20 C19 H191 108.9 . 1_555 1_555 no C20 C19 H192 109.0 . 1_555 1_555 no H191 C19 H192 108.7 . 1_555 1_555 no C19 C20 C21 113.6(4) . 1_555 1_555 yes C19 C20 H201 108.3 . 1_555 1_555 no C19 C20 H202 108.7 . 1_555 1_555 no C21 C20 H201 108.0 . 1_555 1_555 no C21 C20 H202 108.1 . 1_555 1_555 no H201 C20 H202 110.1 . 1_555 1_555 no C20 C21 C22 113.2(5) . 1_555 1_555 yes C20 C21 H211 108.8 . 1_555 1_555 no C20 C21 H212 108.7 . 1_555 1_555 no C22 C21 H211 109.4 . 1_555 1_555 no C22 C21 H212 108.4 . 1_555 1_555 no H211 C21 H212 108.4 . 1_555 1_555 no C21 C22 H221 109.4 . 1_555 1_555 no C21 C22 H222 108.3 . 1_555 1_555 no C21 C22 H223 109.2 . 1_555 1_555 no H221 C22 H222 110.2 . 1_555 1_555 no H221 C22 H223 110.6 . 1_555 1_555 no H222 C22 H223 109.1 . 1_555 1_555 no #---------------------------------------------------------------- loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C7 3.285(6) . 4_444 ? O1 C20 3.413(6) . 4_444 ? O1 C18 3.414(6) . 4_544 ? O2 C19 3.251(6) . 3_858 ? O2 C5 3.494(6) . 4_544 ? O2 C22 3.520(7) . 3_958 ? O2 C9 3.536(6) . 3_858 ? C4 C12 3.492(7) . 4_545 ? C5 C13 3.370(7) . 4_545 ? C6 C15 3.592(7) . 4_645 ? #-----------------------------------------------------------------