# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Emiko Koyama' _publ_contact_author_address ; National Institute of Advanced Industrial Science and Technology, Nanoarchitectonics Research Center Tsukuba Central 4, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8562, Japan ; _publ_contact_author_email e-koyama@aist.go.jp _publ_contact_author_fax ' +81-298-61-3029 ' _publ_contact_author_phone ' +81-298-61-2443 ' _publ_section_title ; STM-based Molecular Detection of "Catch-and-Release" of Protons for Bipyridine Bound to Phenylene-ethynylene Thiol ; loop_ _publ_author_name E.Koyama T.Ishida H.Tokuhisa A.Belaissaoui Y.Nagawa M.Kanesato #============================================================================== data_ek30829a _database_code_depnum_ccdc_archive 'CCDC 231280' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C25 H24 Br F3 N2 O3 S2 ' _chemical_formula_moiety 'C25 H24 Br F3 N2 O3 S2 ' _chemical_formula_weight 601.50 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z #------------------------------------------------------------------------------ _cell_length_a 10.500(10) _cell_length_b 11.15(2) _cell_length_c 12.58(2) _cell_angle_alpha 98.96(7) _cell_angle_beta 93.25(6) _cell_angle_gamma 106.31(5) _cell_volume 1388.4(36) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3103 _cell_measurement_theta_min 4.0 _cell_measurement_theta_max 26.7 _cell_measurement_temperature 193.1 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612.00 _exptl_absorpt_coefficient_mu 1.683 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 11489 _diffrn_reflns_av_R_equivalents 0.110 _diffrn_reflns_theta_max 27.29 _diffrn_measured_fraction_theta_max 1.0000 _diffrn_reflns_theta_full 27.29 _diffrn_measured_fraction_theta_full 1.0000 _diffrn_reflns_limit_h_min 13 _diffrn_reflns_limit_h_max -13 _diffrn_reflns_limit_k_min 14 _diffrn_reflns_limit_k_max -14 _diffrn_reflns_limit_l_min 16 _diffrn_reflns_limit_l_max -16 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 11489 _reflns_number_gt 2389 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0770 _refine_ls_wR_factor_ref 0.1460 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2843 _refine_ls_number_parameters 349 _refine_ls_goodness_of_fit_ref 1.512 _refine_ls_weighting_scheme unit _refine_ls_weighting_details 'w = 1.0' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.81 _refine_diff_density_min -0.52 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Br Br -0.290 2.459 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.017 0.010 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.22510(10) -0.54520(10) -0.01590(10) 0.0465(4) Uani 1.00 1 d . . . S2 S 0.5828(3) 0.8855(3) 0.9219(2) 0.0465(10) Uani 1.00 1 d . . . S3 S -0.0678(3) -0.1273(3) 0.2805(3) 0.0562(10) Uani 1.00 1 d . . . F1 F -0.0090(10) -0.1355(9) 0.4889(7) 0.153(4) Uani 1.00 1 d . . . F2 F -0.1481(8) -0.3044(8) 0.4113(8) 0.110(4) Uani 1.00 1 d . . . F3 F 0.0575(9) -0.2664(9) 0.3846(8) 0.126(4) Uani 1.00 1 d . . . O1 O -0.1782(8) -0.0768(9) 0.3114(9) 0.092(4) Uani 1.00 1 d . . . O2 O -0.0970(10) -0.2250(10) 0.1885(7) 0.120(4) Uani 1.00 1 d . . . O4 O 0.0629(7) -0.0276(7) 0.2882(6) 0.047(3) Uani 1.00 1 d . . . N1 N 0.3321(8) 0.0039(8) 0.3439(7) 0.039(3) Uani 1.00 1 d . . . N2 N 0.2591(8) -0.2161(9) 0.2062(7) 0.046(3) Uani 1.00 1 d . . . C1 C 0.3940(10) -0.1660(10) 0.2288(8) 0.035(4) Uani 1.00 1 d . . . C2 C 0.5260(10) 0.4030(10) 0.5982(9) 0.045(4) Uani 1.00 1 d . . . C3 C 0.5450(10) 0.5180(10) 0.6794(9) 0.046(4) Uani 1.00 1 d . . . C4 C 0.6730(10) 0.6120(10) 0.7054(9) 0.053(4) Uani 1.00 1 d . . . C5 C 0.6900(10) 0.7220(10) 0.7823(8) 0.045(4) Uani 1.00 1 d . . . C6 C 0.5800(10) 0.7470(10) 0.8282(8) 0.037(4) Uani 1.00 1 d . . . C7 C 0.4490(10) 0.6560(10) 0.7966(9) 0.060(4) Uani 1.00 1 d . . . C8 C 0.3510(10) 0.1140(10) 0.4150(7) 0.038(4) Uani 1.00 1 d . . . C9 C 0.5700(10) 0.0270(10) 0.3527(8) 0.041(4) Uani 1.00 1 d . . . C10 C 0.4320(10) 0.5430(10) 0.7243(9) 0.049(4) Uani 1.00 1 d . . . C11 C 0.7650(10) 0.9650(10) 0.9623(9) 0.053(4) Uani 1.00 1 d . . . C12 C 0.2980(10) -0.3910(10) 0.0861(9) 0.043(4) Uani 1.00 1 d . . . C13 C 0.9260(10) 1.1630(10) 1.0805(9) 0.054(4) Uani 1.00 1 d . . . C14 C 0.5950(10) 0.1400(10) 0.4254(8) 0.044(4) Uani 1.00 1 d . . . C15 C 0.9460(10) 1.2890(10) 1.1639(9) 0.046(4) Uani 1.00 1 d . . . C16 C 0.9100(10) 1.2690(10) 1.2770(10) 0.074(5) Uani 1.00 1 d . . . C17 C 0.2130(10) -0.3240(10) 0.1351(9) 0.043(4) Uani 1.00 1 d . . . C18 C 0.4380(10) -0.0420(10) 0.3065(8) 0.036(4) Uani 1.00 1 d . . . C19 C 0.4390(10) -0.3370(10) 0.1108(9) 0.046(4) Uani 1.00 1 d . . . C20 C 0.9340(10) 1.3990(10) 1.3544(9) 0.070(5) Uani 1.00 1 d . . . C21 C 0.7800(10) 1.0850(10) 1.0498(9) 0.052(4) Uani 1.00 1 d . . . C22 C 0.4830(10) 0.1850(10) 0.4591(8) 0.033(3) Uani 1.00 1 d . . . C30 C 0.5090(10) 0.3060(10) 0.5351(9) 0.047(4) Uani 1.00 1 d . . . C31 C 0.4930(10) -0.2200(10) 0.1855(8) 0.039(4) Uani 1.00 1 d . . . C36 C -0.0400(10) -0.2090(10) 0.3910(10) 0.073(5) Uani 1.00 1 d . . . H1 H 0.2262 -0.0558 0.3231 0.044(3) Uiso 1.00 1 d . . . H3 H 0.3760 0.6680 0.8474 0.068 Uiso 1.00 1 c . . . H4 H 0.2680 0.1400 0.4462 0.047 Uiso 1.00 1 c . . . H5 H 0.3500 0.4760 0.7034 0.053 Uiso 1.00 1 c . . . H6 H 0.9710 1.1130 1.1132 0.062(4) Uiso 1.00 1 c . . . H7 H 0.5050 -0.3890 0.0686 0.056(4) Uiso 1.00 1 c . . . H8 H 0.9140 1.3850 1.4249 0.075(5) Uiso 1.00 1 c . . . H9 H 0.7420 1.0590 1.1124 0.058(4) Uiso 1.00 1 c . . . H10 H 0.6040 -0.1950 0.2209 0.046(4) Uiso 1.00 1 c . . . H11 H 0.8890 1.3330 1.1367 0.053(4) Uiso 1.00 1 c . . . H12 H 1.0250 1.4480 1.3575 0.076(5) Uiso 1.00 1 c . . . H13 H 0.8410 0.9320 0.9696 0.057(4) Uiso 1.00 1 c . . . H14 H 0.8030 1.2350 1.2710 0.083(5) Uiso 1.00 1 c . . . H15 H 0.1200 -0.3600 0.1172 0.047(4) Uiso 1.00 1 c . . . H17 H 0.7470 0.5970 0.6723 0.061(4) Uiso 1.00 1 c . . . H18 H 0.7760 0.7820 0.8019 0.049(4) Uiso 1.00 1 c . . . H19 H 0.8100 0.9980 0.8778 0.057(4) Uiso 1.00 1 c . . . H20 H 0.7320 1.1360 1.0219 0.058(4) Uiso 1.00 1 c . . . H21 H 0.9640 1.1820 1.0162 0.062(4) Uiso 1.00 1 c . . . H22 H 1.0360 1.3410 1.1694 0.053(4) Uiso 1.00 1 c . . . H23 H 0.9650 1.2430 1.3170 0.083(5) Uiso 1.00 1 c . . . H24 H 0.8780 1.4430 1.3271 0.076(5) Uiso 1.00 1 c . . . H25 H 0.6850 0.1890 0.4516 0.049(4) Uiso 1.00 1 c . . . H26 H 0.6650 0.0160 0.3221 0.048(4) Uiso 1.00 1 c . . . 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 Br1 0.0501(9) 0.0351(8) 0.0495(8) 0.0100(6) 0.0082(6) -0.0028(6) S2 0.035(2) 0.049(2) 0.049(2) 0.011(2) 0.006(2) -0.009(2) S3 0.034(2) 0.060(2) 0.064(2) 0.013(2) -0.008(2) -0.014(2) F1 0.260(10) 0.084(7) 0.084(7) 0.024(8) -0.009(8) -0.022(6) F2 0.074(6) 0.070(6) 0.178(9) -0.005(5) 0.035(6) 0.037(6) F3 0.110(7) 0.138(9) 0.190(10) 0.079(7) 0.090(7) 0.106(7) O1 0.027(5) 0.087(8) 0.170(10) 0.026(5) 0.021(6) 0.026(7) O2 0.140(10) 0.098(9) 0.071(7) -0.011(7) -0.018(7) -0.041(6) O4 0.025(5) 0.054(5) 0.066(5) 0.010(4) 0.011(4) 0.023(4) N1 0.022(5) 0.049(6) 0.040(6) 0.006(5) -0.002(4) 0.001(5) N2 0.022(6) 0.046(6) 0.060(7) 0.003(5) 0.002(5) -0.007(5) C1 0.033(7) 0.037(7) 0.042(7) 0.010(6) 0.013(6) 0.022(6) C2 0.033(7) 0.048(8) 0.049(8) 0.002(6) -0.005(6) 0.013(7) C3 0.044(8) 0.042(8) 0.048(8) 0.015(7) 0.002(6) -0.008(6) C4 0.037(8) 0.051(8) 0.064(9) 0.011(7) 0.000(6) -0.003(7) C5 0.043(8) 0.039(8) 0.039(7) 0.006(6) -0.001(6) -0.019(6) C6 0.029(7) 0.043(7) 0.036(7) 0.009(6) -0.002(5) 0.000(6) C7 0.039(8) 0.069(9) 0.063(9) 0.026(7) 0.007(6) -0.031(7) C8 0.058(8) 0.044(7) 0.017(6) 0.020(6) 0.023(5) 0.006(5) C9 0.019(7) 0.054(8) 0.046(7) 0.004(6) 0.009(5) 0.010(6) C10 0.032(7) 0.045(8) 0.056(8) -0.004(6) 0.008(6) -0.005(6) C11 0.016(7) 0.070(9) 0.057(8) 0.013(6) -0.013(6) -0.033(7) C12 0.047(8) 0.045(8) 0.038(7) 0.013(7) 0.006(6) 0.012(6) C13 0.049(8) 0.049(8) 0.056(8) 0.011(7) -0.006(6) -0.001(7) C14 0.030(7) 0.051(8) 0.042(7) 0.007(6) 0.004(5) -0.012(6) C15 0.043(8) 0.036(8) 0.053(8) 0.010(6) -0.001(6) -0.009(6) C16 0.080(10) 0.060(10) 0.062(9) 0.012(8) -0.011(8) -0.027(8) C17 0.037(7) 0.032(7) 0.048(7) -0.002(6) 0.012(6) -0.005(6) C18 0.024(7) 0.041(8) 0.040(7) 0.011(6) 0.001(5) 0.000(6) C19 0.041(8) 0.047(8) 0.053(8) 0.016(6) 0.011(6) 0.011(7) C20 0.065(9) 0.055(9) 0.069(9) 0.005(7) 0.010(7) -0.025(7) C21 0.035(8) 0.057(9) 0.054(8) 0.010(6) 0.004(6) -0.013(7) C22 0.021(7) 0.039(7) 0.033(6) -0.002(6) 0.009(5) 0.009(5) C30 0.050(8) 0.047(8) 0.037(7) 0.012(7) -0.008(6) -0.008(6) C31 0.019(6) 0.051(8) 0.044(7) 0.017(6) -0.002(5) -0.010(6) C36 0.070(10) 0.027(8) 0.120(10) 0.009(8) 0.042(9) 0.007(8) #============================================================================== _computing_data_collection PROCESS _computing_cell_refinement PROCESS _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure Ver. 3.10' _computing_molecular_graphics ? #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================