# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name _publ_author_address M.Morimoto ; Department of Chemistry and Research Center for Smart Molecules Rikkyo University Nishi-Ikebukuro 3-34-1, Toshima-ku, Tokyo 171-8501, Japan ; M.Irie ; Department of Chemistry and Research Center for Smart Molecules Rikkyo University Nishi-Ikebukuro 3-34-1, Toshima-ku, Tokyo 171-8501, Japan ; _publ_contact_author_name 'Masakazu Morimoto' _publ_contact_author_address ; Nishi-Ikebukuro 3-34-1 Toshima-ku Tokyo 171-8501 ; _publ_contact_author_email m-morimoto@rikkyo.ac.jp _publ_contact_author_fax ; +81-3-3985-2397 ; _publ_contact_author_phone ; +81-3-3985-2397 ; _publ_section_title ; Photochemical control of dielectric properties based on intermolecular proton transfer in a hydrogen-bonded diarylethene crystal ; # Attachment '- morimoto_1o.cif' data_1o _database_code_depnum_ccdc_archive 'CCDC 805211' _publ_section_abstract ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H26 F6 N4 S2' _chemical_formula_weight 656.70 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 11.0597(8) _cell_length_b 29.913(2) _cell_length_c 9.2876(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3072.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 8404 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.46 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8892 _exptl_absorpt_correction_T_max 0.9881 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; _exptl_special_details ; The single crystal was obtained by recrystallization of compound 1o from chloroform. ; _diffrn_ambient_temperature 93(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 'omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 237 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.7 _diffrn_reflns_number 23470 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3136 _reflns_number_gt 2959 _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. The asymmetric unit contains a half of 1o molecule. 1o molecule lies on a two-fold axis, and a symmetry operation of C2 builds the entire structure of the molecule. The hexafluorocyclopentene ring is disordered in the ratio of 50 : 50. The N-H proton in the imidazoline ring occupies the two sites (H51 and H52) on the nitrogen atoms in the ratio of 50 : 50. ; _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^)+(0.0785P)^2^+2.6229P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3136 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1521 _refine_ls_wR_factor_gt 0.1496 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 0.71840(18) 0.05681(7) 0.1571(2) 0.0281(4) Uani 1 1 d . . . C2 C 0.79406(17) 0.05141(6) 0.2733(2) 0.0242(4) Uani 1 1 d . A . C3 C 0.89848(18) 0.07941(6) 0.2661(2) 0.0254(4) Uani 1 1 d . . . H3 H 0.9591 0.0799 0.3385 0.030 Uiso 1 1 calc R . . C4 C 0.90286(18) 0.10528(6) 0.1456(2) 0.0264(4) Uani 1 1 d . . . C5 C 0.77096(18) 0.02130(7) 0.3943(2) 0.0260(4) Uani 1 1 d . . . C7 C 0.7500 0.0000 0.6441(3) 0.0355(7) Uani 1 2 d S . . C8 C 0.59903(19) 0.03568(8) 0.1243(3) 0.0361(5) Uani 1 1 d . . . H8A H 0.6115 0.0093 0.0637 0.054 Uiso 1 1 calc R . . H8B H 0.5476 0.0572 0.0734 0.054 Uiso 1 1 calc R . . H8C H 0.5597 0.0267 0.2144 0.054 Uiso 1 1 calc R . . C9 C 0.99202(18) 0.13925(6) 0.1054(2) 0.0293(5) Uani 1 1 d . . . C10 C 1.0800(2) 0.15261(7) 0.2039(3) 0.0358(5) Uani 1 1 d . . . H10 H 1.0847 0.1383 0.2951 0.043 Uiso 1 1 calc R . . C11 C 1.1603(2) 0.18640(8) 0.1704(3) 0.0421(6) Uani 1 1 d . . . H11 H 1.2193 0.1950 0.2394 0.051 Uiso 1 1 calc R . . C12 C 1.1569(2) 0.20791(7) 0.0395(3) 0.0407(6) Uani 1 1 d . . . C13 C 1.0709(2) 0.19460(9) -0.0586(3) 0.0508(7) Uani 1 1 d . . . H13 H 1.0669 0.2091 -0.1495 0.061 Uiso 1 1 calc R . . C14 C 0.9897(2) 0.16043(8) -0.0275(3) 0.0428(6) Uani 1 1 d . . . H14 H 0.9322 0.1515 -0.0978 0.051 Uiso 1 1 calc R . . C15 C 1.2411(3) 0.24546(9) 0.0085(4) 0.0592(9) Uani 1 1 d . . . C16 C 1.3887(3) 0.29638(10) 0.0313(5) 0.0780(13) Uani 1 1 d . . . H16A H 1.4774 0.2922 0.0266 0.094 Uiso 1 1 calc R . . H16B H 1.3708 0.3237 0.0877 0.094 Uiso 1 1 calc R . . C6A C 0.7746(6) 0.04068(19) 0.5448(5) 0.0294(13) Uiso 0.50 1 d P A 1 F1A F 0.6883(4) 0.07181(11) 0.5691(3) 0.0484(8) Uani 0.50 1 d P A 1 F2A F 0.8806(4) 0.05931(13) 0.5781(3) 0.0480(8) Uani 0.50 1 d P A 1 C6B C 0.8093(6) 0.03429(19) 0.5452(6) 0.0327(14) Uiso 0.50 1 d P A 2 F1B F 0.7732(4) 0.07702(10) 0.5748(3) 0.0511(9) Uani 0.50 1 d P A 2 F2B F 0.9313(3) 0.03413(15) 0.5633(3) 0.0491(8) Uani 0.50 1 d P A 2 C17 C 1.3359(5) 0.29920(15) -0.1146(6) 0.1088(17) Uani 1 1 d . . . H17A H 1.3118 0.3303 -0.1372 0.131 Uiso 1 1 calc R . . H17B H 1.3946 0.2889 -0.1879 0.131 Uiso 1 1 calc R . . F3 F 0.6442(3) 0.01710(14) 0.6929(4) 0.0495(9) Uani 0.50 1 d P . . F4 F 0.8184(4) -0.00939(14) 0.7586(4) 0.0514(10) Uani 0.50 1 d P . . N1 N 1.3292(2) 0.25697(8) 0.0947(5) 0.0652(10) Uani 1 1 d . . . N2 N 1.2293(3) 0.26963(10) -0.1107(4) 0.0762(10) Uani 1 1 d . . . S1 S 0.77635(5) 0.095798(18) 0.03991(6) 0.0321(2) Uani 1 1 d . . . H52 H 1.241(5) 0.251(2) -0.181(6) 0.044(18) Uiso 0.50 1 d P . . H51 H 1.328(8) 0.257(3) 0.174(8) 0.08(3) Uiso 0.50 1 d P . . 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 0.0252(10) 0.0232(10) 0.0357(11) 0.0038(8) 0.0018(8) 0.0011(8) C2 0.0216(9) 0.0191(9) 0.0320(10) -0.0022(7) 0.0032(8) 0.0003(7) C3 0.0237(10) 0.0194(9) 0.0330(10) -0.0026(8) 0.0026(8) 0.0003(7) C4 0.0230(10) 0.0194(9) 0.0368(11) -0.0026(8) 0.0038(8) 0.0030(7) C5 0.0233(10) 0.0266(10) 0.0283(10) -0.0015(8) 0.0003(8) -0.0025(7) C7 0.0350(16) 0.0444(18) 0.0270(15) 0.000 0.000 -0.0091(14) C8 0.0254(11) 0.0353(11) 0.0474(13) 0.0110(10) -0.0093(10) -0.0031(9) C9 0.0239(10) 0.0204(9) 0.0437(12) 0.0014(8) 0.0122(9) 0.0032(7) C10 0.0386(12) 0.0273(10) 0.0416(12) -0.0035(9) 0.0122(10) -0.0067(9) C11 0.0383(13) 0.0314(11) 0.0566(15) -0.0090(10) 0.0143(11) -0.0091(10) C12 0.0295(12) 0.0226(10) 0.0700(17) 0.0064(10) 0.0193(11) 0.0032(9) C13 0.0358(13) 0.0451(14) 0.0714(18) 0.0318(13) 0.0119(13) 0.0044(11) C14 0.0271(11) 0.0432(13) 0.0582(16) 0.0187(11) 0.0027(11) 0.0024(10) C15 0.0422(15) 0.0292(12) 0.106(2) 0.0095(15) 0.0360(17) 0.0014(11) C16 0.0446(17) 0.0378(15) 0.152(4) 0.0089(19) 0.039(2) -0.0095(13) F1A 0.062(2) 0.0381(17) 0.0451(17) -0.0135(13) 0.0101(17) 0.0050(16) F2A 0.052(2) 0.055(2) 0.0369(16) -0.0053(16) -0.0068(16) -0.0323(18) F1B 0.081(3) 0.0314(17) 0.0404(17) -0.0114(12) 0.0112(18) -0.0120(17) F2B 0.0389(19) 0.074(2) 0.0344(15) 0.0044(17) -0.0076(14) -0.0284(17) C17 0.129(4) 0.080(3) 0.117(4) 0.021(3) 0.043(3) -0.060(3) F3 0.046(2) 0.056(2) 0.046(2) -0.0055(19) 0.0154(17) -0.0120(16) F4 0.058(2) 0.064(2) 0.0315(17) 0.0079(17) -0.0142(16) -0.0240(19) N1 0.0339(13) 0.0281(12) 0.134(3) 0.0026(16) 0.0214(17) -0.0073(9) N2 0.072(2) 0.0493(16) 0.107(3) 0.0354(18) 0.0309(19) -0.0114(14) S1 0.0272(3) 0.0299(3) 0.0393(3) 0.0107(2) -0.0016(2) -0.0005(2) _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 1.375(3) . ? C1 C8 1.495(3) . ? C1 S1 1.719(2) . ? C2 C3 1.428(3) . ? C2 C5 1.462(3) . ? C3 C4 1.362(3) . ? C3 H3 0.9500 . ? C4 C9 1.464(3) . ? C4 S1 1.733(2) . ? C5 C5 1.356(4) 2_655 ? C5 C6A 1.513(5) . ? C5 C6B 1.514(6) . ? C7 F4 1.334(4) 2_655 ? C7 F4 1.334(4) . ? C7 F3 1.355(4) . ? C7 F3 1.355(4) 2_655 ? C7 C6B 1.525(6) . ? C7 C6B 1.526(6) 2_655 ? C7 C6A 1.551(5) . ? C7 C6A 1.551(5) 2_655 ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.387(3) . ? C9 C10 1.393(3) . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? C11 C12 1.376(4) . ? C11 H11 0.9500 . ? C12 C13 1.375(4) . ? C12 C15 1.487(3) . ? C13 C14 1.391(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N1 1.307(5) . ? C15 N2 1.329(5) . ? C16 N1 1.473(4) . ? C16 C17 1.478(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C6A F2A 1.334(6) . ? C6A F1A 1.353(7) . ? C6B F2B 1.361(8) . ? C6B F1B 1.367(7) . ? C17 N2 1.474(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? F3 F4 0.772(4) 2_655 ? F4 F3 0.772(4) 2_655 ? F4 F4 1.614(9) 2_655 ? N1 H51 0.74(7) . ? N2 H52 0.86(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 C8 130.36(19) . . ? C2 C1 S1 110.47(15) . . ? C8 C1 S1 119.13(16) . . ? C1 C2 C3 112.73(18) . . ? C1 C2 C5 124.68(18) . . ? C3 C2 C5 122.58(18) . . ? C4 C3 C2 113.61(19) . . ? C4 C3 H3 123.2 . . ? C2 C3 H3 123.2 . . ? C3 C4 C9 128.9(2) . . ? C3 C4 S1 110.12(15) . . ? C9 C4 S1 120.86(16) . . ? C5 C5 C2 129.68(11) 2_655 . ? C5 C5 C6A 111.7(2) 2_655 . ? C2 C5 C6A 118.0(2) . . ? C5 C5 C6B 109.7(2) 2_655 . ? C2 C5 C6B 120.3(3) . . ? F4 C7 F4 74.4(4) 2_655 . ? F4 C7 F3 107.6(4) . . ? F4 C7 F3 107.6(4) 2_655 2_655 ? F3 C7 F3 140.9(4) . 2_655 ? F4 C7 C6B 125.6(3) 2_655 . ? F4 C7 C6B 112.2(3) . . ? F3 C7 C6B 108.6(3) . . ? F3 C7 C6B 94.8(3) 2_655 . ? F4 C7 C6B 112.2(3) 2_655 2_655 ? F4 C7 C6B 125.6(3) . 2_655 ? F3 C7 C6B 94.8(3) . 2_655 ? F3 C7 C6B 108.6(3) 2_655 2_655 ? C6B C7 C6B 105.9(4) . 2_655 ? F4 C7 C6A 114.1(3) 2_655 . ? F4 C7 C6A 122.7(3) . . ? F3 C7 C6A 93.1(3) . . ? F3 C7 C6A 110.1(3) 2_655 . ? C6B C7 C6A 104.1(3) 2_655 . ? F4 C7 C6A 122.7(3) 2_655 2_655 ? F4 C7 C6A 114.1(3) . 2_655 ? F3 C7 C6A 110.1(3) . 2_655 ? F3 C7 C6A 93.1(3) 2_655 2_655 ? C6B C7 C6A 104.1(3) . 2_655 ? C6A C7 C6A 107.0(4) . 2_655 ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 117.8(2) . . ? C14 C9 C4 122.1(2) . . ? C10 C9 C4 120.1(2) . . ? C11 C10 C9 120.7(2) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C10 121.5(2) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C13 C12 C11 118.0(2) . . ? C13 C12 C15 121.6(3) . . ? C11 C12 C15 120.4(3) . . ? C12 C13 C14 121.4(2) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C9 C14 C13 120.5(3) . . ? C9 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? N1 C15 N2 116.1(3) . . ? N1 C15 C12 123.2(3) . . ? N2 C15 C12 120.7(3) . . ? N1 C16 C17 103.6(3) . . ? N1 C16 H16A 111.0 . . ? C17 C16 H16A 111.0 . . ? N1 C16 H16B 111.0 . . ? C17 C16 H16B 111.0 . . ? H16A C16 H16B 109.0 . . ? F2A C6A F1A 107.1(5) . . ? F2A C6A C5 113.4(4) . . ? F1A C6A C5 113.5(4) . . ? F2A C6A C7 110.1(4) . . ? F1A C6A C7 108.5(4) . . ? C5 C6A C7 104.1(3) . . ? F2B C6B F1B 105.5(5) . . ? F2B C6B C5 113.0(4) . . ? F1B C6B C5 110.2(4) . . ? F2B C6B C7 110.5(4) . . ? F1B C6B C7 112.4(4) . . ? C5 C6B C7 105.4(4) . . ? N2 C17 C16 105.1(3) . . ? N2 C17 H17A 110.7 . . ? C16 C17 H17A 110.7 . . ? N2 C17 H17B 110.7 . . ? C16 C17 H17B 110.7 . . ? H17A C17 H17B 108.8 . . ? F4 F3 C7 71.9(5) 2_655 . ? F3 F4 C7 74.8(4) 2_655 . ? F3 F4 F4 127.3(5) 2_655 2_655 ? C7 F4 F4 52.8(2) . 2_655 ? C15 N1 C16 107.4(4) . . ? C15 N1 H51 127(7) . . ? C16 N1 H51 115(7) . . ? C15 N2 C17 105.5(4) . . ? C15 N2 H52 106(4) . . ? C17 N2 H52 104(4) . . ? C1 S1 C4 93.06(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.647 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.068 data_1o-UV _database_code_depnum_ccdc_archive 'CCDC 805212' _publ_section_abstract ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H26 F6 N4 S2' _chemical_formula_weight 656.70 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 11.0788(12) _cell_length_b 29.771(3) _cell_length_c 9.3271(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3076.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6842 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 27.33 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8893 _exptl_absorpt_correction_T_max 0.9881 _exptl_absorpt_process_details ; SADABS; Scheldrick 1996 ; _exptl_special_details ; The single crystal of 1o was irradiated with 400 nm light for 15 min. ; _diffrn_ambient_temperature 93(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 'omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 184 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.2 _diffrn_reflns_number 22712 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3036 _reflns_number_gt 2784 _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. The asymmetric unit contains a half of 1o molecule. 1o molecule lies on a two-fold axis, and a symmetry operation of C2 builds the entire structure of the molecule. The hexafluorocyclopentene ring is disordered in the ratio of 50 : 50. The N-H proton in the imidazoline ring occupies the two sites (H51 and H52) on the nitrogen atoms in the ratio of 50 : 50. After irradiation with 400 nm light, residual high electron-density peaks were observed near the thiophene rings of the open-ring isomer 1o. The peaks are reasonably assigned to the sulfur and carbon atoms of the photogenerated closed-ring isomer 1c (S1B and C1B). The occupancy ratio for these atoms is 9%. ; _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^)+(0.0849P)^2^+3.2241P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3036 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0676 _refine_ls_wR_factor_ref 0.1751 _refine_ls_wR_factor_gt 0.1717 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 C2 C 0.7946(2) 0.05131(8) 0.2745(3) 0.0303(5) Uani 1 1 d . . . C3 C 0.8981(2) 0.07968(7) 0.2670(3) 0.0297(5) Uani 1 1 d . C . H3 H 0.9579 0.0808 0.3400 0.036 Uiso 1 1 calc R . . C4 C 0.9032(2) 0.10503(8) 0.1456(3) 0.0322(6) Uani 1 1 d . . . C5 C 0.7712(2) 0.02140(8) 0.3945(3) 0.0323(6) Uani 1 1 d . . . C7 C 0.7500 0.0000 0.6436(4) 0.0429(9) Uani 1 2 d S . . C8 C 0.5997(2) 0.03602(10) 0.1252(4) 0.0451(7) Uani 1 1 d . . . H8A H 0.6116 0.0096 0.0641 0.068 Uiso 1 1 calc R A 3 H8B H 0.5481 0.0578 0.0756 0.068 Uiso 1 1 calc R A 3 H8C H 0.5611 0.0269 0.2151 0.068 Uiso 1 1 calc R A 3 C9 C 0.9922(2) 0.13917(8) 0.1057(3) 0.0339(6) Uani 1 1 d . C . C10 C 1.0803(3) 0.15235(9) 0.2029(3) 0.0418(7) Uani 1 1 d . . . H10 H 1.0854 0.1379 0.2935 0.050 Uiso 1 1 calc R C . C11 C 1.1604(3) 0.18624(10) 0.1694(4) 0.0487(8) Uani 1 1 d . C . H11 H 1.2196 0.1947 0.2379 0.058 Uiso 1 1 calc R . . C12 C 1.1568(3) 0.20788(9) 0.0402(4) 0.0477(8) Uani 1 1 d . . . C13 C 1.0705(3) 0.19491(12) -0.0567(4) 0.0617(10) Uani 1 1 d . C . H13 H 1.0662 0.2096 -0.1470 0.074 Uiso 1 1 calc R . . C14 C 0.9892(3) 0.16069(11) -0.0258(4) 0.0519(8) Uani 1 1 d . . . H14 H 0.9311 0.1520 -0.0954 0.062 Uiso 1 1 calc R C . C15 C 1.2413(3) 0.24569(11) 0.0091(5) 0.0687(12) Uani 1 1 d . C . C16 C 1.3874(4) 0.29693(13) 0.0319(7) 0.0914(18) Uani 1 1 d . C . H16A H 1.3690 0.3245 0.0873 0.110 Uiso 1 1 calc R . . H16B H 1.4761 0.2929 0.0281 0.110 Uiso 1 1 calc R . . C6A C 0.7759(7) 0.0407(2) 0.5435(7) 0.0346(16) Uiso 0.50 1 d P B 1 F1A F 0.6880(5) 0.07192(13) 0.5686(4) 0.0573(10) Uani 0.50 1 d P B 1 F2A F 0.8798(5) 0.05996(17) 0.5786(4) 0.0565(11) Uani 0.50 1 d P B 1 C6B C 0.8106(8) 0.0339(3) 0.5466(8) 0.044(2) Uiso 0.50 1 d P B 2 F1B F 0.7735(6) 0.07757(13) 0.5744(5) 0.0627(12) Uani 0.50 1 d P B 2 F2B F 0.9309(4) 0.03414(18) 0.5632(4) 0.0586(11) Uani 0.50 1 d P B 2 C17 C 1.3365(6) 0.29955(19) -0.1123(8) 0.126(2) Uani 1 1 d . C . H17A H 1.3961 0.2895 -0.1846 0.151 Uiso 1 1 calc R . . H17B H 1.3121 0.3307 -0.1350 0.151 Uiso 1 1 calc R . . F3 F 0.6443(4) 0.01768(19) 0.6909(5) 0.0594(12) Uani 0.50 1 d P . . F4 F 0.8178(5) -0.00944(19) 0.7566(5) 0.0618(13) Uani 0.50 1 d P . . N1 N 1.3286(3) 0.25746(10) 0.0965(6) 0.0764(12) Uani 1 1 d . . . N2 N 1.2305(4) 0.26951(13) -0.1110(6) 0.0905(14) Uani 1 1 d . . . C1A C 0.7187(2) 0.05702(9) 0.1570(3) 0.0299(6) Uani 0.913(3) 1 d P C 3 S1A S 0.77694(6) 0.09606(2) 0.04008(8) 0.0346(3) Uani 0.913(3) 1 d P C 3 C1B C 0.754(4) 0.0284(14) 0.184(4) 0.050(9) Uiso 0.087(3) 1 d P . 4 S1B S 0.8355(11) 0.0533(4) 0.0399(13) 0.068(4) Uiso 0.087(3) 1 d P C 4 H52 H 1.246(7) 0.247(3) -0.177(7) 0.07(3) Uiso 0.50 1 d P . . H51 H 1.321(8) 0.249(4) 0.181(8) 0.08(3) Uiso 0.50 1 d P . . 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 C2 0.0246(11) 0.0243(11) 0.0420(14) -0.0068(10) 0.0056(10) -0.0018(9) C3 0.0263(11) 0.0202(10) 0.0426(13) -0.0027(10) 0.0005(10) -0.0009(9) C4 0.0252(12) 0.0280(12) 0.0435(14) -0.0032(10) 0.0039(10) 0.0029(9) C5 0.0262(12) 0.0298(12) 0.0407(14) -0.0039(11) 0.0016(10) -0.0034(9) C7 0.039(2) 0.050(2) 0.040(2) 0.000 0.000 -0.0115(18) C8 0.0305(14) 0.0417(15) 0.0631(18) 0.0165(13) -0.0091(13) -0.0029(12) C9 0.0263(12) 0.0277(12) 0.0478(14) 0.0021(11) 0.0128(11) 0.0032(9) C10 0.0439(15) 0.0346(14) 0.0470(15) -0.0017(12) 0.0121(13) -0.0091(12) C11 0.0440(16) 0.0391(15) 0.0629(19) -0.0071(14) 0.0155(14) -0.0115(12) C12 0.0336(15) 0.0296(13) 0.080(2) 0.0084(13) 0.0212(15) 0.0047(11) C13 0.0432(17) 0.056(2) 0.085(2) 0.0410(19) 0.0151(17) 0.0069(15) C14 0.0313(14) 0.0568(19) 0.068(2) 0.0228(16) 0.0010(14) 0.0038(13) C15 0.051(2) 0.0367(16) 0.119(3) 0.016(2) 0.043(2) 0.0057(15) C16 0.054(2) 0.0435(19) 0.177(6) 0.012(3) 0.047(3) -0.0098(17) F1A 0.069(3) 0.044(2) 0.059(2) -0.0162(17) 0.015(2) 0.003(2) F2A 0.057(3) 0.061(3) 0.051(2) -0.009(2) -0.006(2) -0.038(2) F1B 0.093(4) 0.036(2) 0.059(2) -0.0160(17) 0.019(3) -0.016(2) F2B 0.045(2) 0.085(3) 0.046(2) 0.001(2) -0.0053(18) -0.034(2) C17 0.151(6) 0.084(3) 0.141(5) 0.026(4) 0.058(5) -0.058(4) F3 0.051(3) 0.066(3) 0.061(3) -0.003(3) 0.021(2) -0.012(2) F4 0.064(3) 0.073(3) 0.048(3) 0.006(2) -0.019(2) -0.029(3) N1 0.0401(16) 0.0349(15) 0.154(4) 0.004(2) 0.025(2) -0.0091(12) N2 0.083(3) 0.060(2) 0.129(3) 0.045(2) 0.040(3) -0.0070(19) C1A 0.0240(13) 0.0242(13) 0.0415(15) 0.0039(11) -0.0002(11) 0.0000(10) S1A 0.0282(4) 0.0309(4) 0.0446(5) 0.0123(3) -0.0033(3) -0.0024(3) _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 C2 C1B 1.18(4) . ? C2 C1A 1.391(4) . ? C2 C3 1.426(3) . ? C2 C5 1.453(4) . ? C3 C4 1.362(4) . ? C3 H3 0.9500 . ? C4 C9 1.464(3) . ? C4 S1A 1.731(3) . ? C4 S1B 1.977(12) . ? C5 C5 1.358(5) 2_655 ? C5 C6A 1.505(7) . ? C5 C6B 1.531(8) . ? C7 F4 1.325(6) 2_655 ? C7 F4 1.325(6) . ? C7 F3 1.357(5) 2_655 ? C7 F3 1.357(5) . ? C7 C6B 1.512(8) . ? C7 C6B 1.512(8) 2_655 ? C7 C6A 1.557(7) . ? C7 C6A 1.557(7) 2_655 ? C8 C1A 1.489(4) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.384(4) . ? C9 C10 1.389(4) . ? C10 C11 1.380(4) . ? C10 H10 0.9500 . ? C11 C12 1.367(5) . ? C11 H11 0.9500 . ? C12 C13 1.371(5) . ? C12 C15 1.492(4) . ? C13 C14 1.391(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N1 1.312(6) . ? C15 N2 1.331(6) . ? C16 C17 1.461(8) . ? C16 N1 1.472(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C6A F2A 1.326(8) . ? C6A F1A 1.366(9) . ? C6B F2B 1.341(10) . ? C6B F1B 1.389(9) . ? C17 N2 1.476(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? F3 F4 0.782(5) 2_655 ? F4 F3 0.782(5) 2_655 ? F4 F4 1.604(12) 2_655 ? N1 H51 0.83(7) . ? N2 H52 0.92(8) . ? C1A S1A 1.719(3) . ? C1B C1B 1.69(8) 2_655 ? C1B S1B 1.78(4) . ? 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 C1B C2 C3 128.3(18) . . ? C1A C2 C3 112.0(2) . . ? C1B C2 C5 97.4(19) . . ? C1A C2 C5 125.0(2) . . ? C3 C2 C5 122.9(2) . . ? C4 C3 C2 113.7(2) . . ? C4 C3 H3 123.1 . . ? C2 C3 H3 123.1 . . ? C3 C4 C9 128.6(2) . . ? C3 C4 S1A 110.69(18) . . ? C9 C4 S1A 120.4(2) . . ? C3 C4 S1B 88.1(4) . . ? C9 C4 S1B 132.1(4) . . ? C5 C5 C2 129.53(14) 2_655 . ? C5 C5 C6A 111.8(3) 2_655 . ? C2 C5 C6A 118.1(3) . . ? C5 C5 C6B 109.0(3) 2_655 . ? C2 C5 C6B 121.0(3) . . ? F4 C7 F4 74.5(6) 2_655 . ? F4 C7 F3 108.2(5) 2_655 2_655 ? F4 C7 F3 108.2(5) . . ? F3 C7 F3 142.1(6) 2_655 . ? F4 C7 C6B 125.9(4) 2_655 . ? F4 C7 C6B 111.4(4) . . ? F3 C7 C6B 94.0(4) 2_655 . ? F3 C7 C6B 108.6(4) . . ? F4 C7 C6B 111.4(4) 2_655 2_655 ? F4 C7 C6B 125.9(4) . 2_655 ? F3 C7 C6B 108.6(4) 2_655 2_655 ? F3 C7 C6B 94.0(4) . 2_655 ? C6B C7 C6B 106.5(6) . 2_655 ? F4 C7 C6A 114.6(4) 2_655 . ? F4 C7 C6A 122.5(3) . . ? F3 C7 C6A 109.7(4) 2_655 . ? F3 C7 C6A 93.0(4) . . ? C6B C7 C6A 104.0(3) 2_655 . ? F4 C7 C6A 122.5(3) 2_655 2_655 ? F4 C7 C6A 114.6(4) . 2_655 ? F3 C7 C6A 93.0(4) 2_655 2_655 ? F3 C7 C6A 109.7(4) . 2_655 ? C6B C7 C6A 104.0(3) . 2_655 ? C6A C7 C6A 106.3(5) . 2_655 ? C14 C9 C10 117.7(2) . . ? C14 C9 C4 122.0(3) . . ? C10 C9 C4 120.2(2) . . ? C11 C10 C9 120.7(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C10 121.7(3) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 118.0(3) . . ? C11 C12 C15 120.5(3) . . ? C13 C12 C15 121.5(3) . . ? C12 C13 C14 121.4(3) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C9 C14 C13 120.5(3) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? N1 C15 N2 116.5(4) . . ? N1 C15 C12 122.9(4) . . ? N2 C15 C12 120.5(4) . . ? C17 C16 N1 104.4(4) . . ? C17 C16 H16A 110.9 . . ? N1 C16 H16A 110.9 . . ? C17 C16 H16B 110.9 . . ? N1 C16 H16B 110.9 . . ? H16A C16 H16B 108.9 . . ? F2A C6A F1A 106.4(6) . . ? F2A C6A C5 115.0(5) . . ? F1A C6A C5 113.2(5) . . ? F2A C6A C7 110.4(5) . . ? F1A C6A C7 107.1(5) . . ? C5 C6A C7 104.5(4) . . ? F2B C6B F1B 105.5(6) . . ? F2B C6B C7 112.1(6) . . ? F1B C6B C7 112.4(6) . . ? F2B C6B C5 113.1(6) . . ? F1B C6B C5 108.4(6) . . ? C7 C6B C5 105.4(5) . . ? C16 C17 N2 105.5(4) . . ? C16 C17 H17A 110.6 . . ? N2 C17 H17A 110.6 . . ? C16 C17 H17B 110.6 . . ? N2 C17 H17B 110.6 . . ? H17A C17 H17B 108.8 . . ? F4 F3 C7 70.8(7) 2_655 . ? F3 F4 C7 75.3(6) 2_655 . ? F3 F4 F4 127.7(6) 2_655 2_655 ? C7 F4 F4 52.7(3) . 2_655 ? C15 N1 C16 106.6(4) . . ? C15 N1 H51 116(7) . . ? C16 N1 H51 132(7) . . ? C15 N2 C17 105.0(5) . . ? C15 N2 H52 99(5) . . ? C17 N2 H52 107(5) . . ? C2 C1A C8 129.8(2) . . ? C2 C1A S1A 110.84(18) . . ? C8 C1A S1A 119.3(2) . . ? C1A S1A C4 92.69(13) . . ? C2 C1B C1B 127(3) . 2_655 ? C2 C1B S1B 96(2) . . ? C1B C1B S1B 116(2) 2_655 . ? C1B S1B C4 98.1(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.510 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.067 # Attachment '- morimoto_1o-Vis.cif' data_1o-Vis _database_code_depnum_ccdc_archive 'CCDC 805213' _publ_section_abstract ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H26 F6 N4 S2' _chemical_formula_weight 656.70 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 11.0607(10) _cell_length_b 29.907(3) _cell_length_c 9.2892(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3072.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 5787 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.34 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8892 _exptl_absorpt_correction_T_max 0.9881 _exptl_absorpt_process_details ; SADABS; Scheldrick 1996 ; _exptl_special_details ; The single crystal of 1o-UV was irradiated with visible (> 520 nm) light for 60 min. ; _diffrn_ambient_temperature 93(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 'omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 159 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.6 _diffrn_reflns_number 22902 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3036 _reflns_number_gt 2843 _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. The asymmetric unit contains a half of 1o molecule. 1o molecule lies on a two-fold axis, and a symmetry operation of C2 builds the entire structure of the molecule. The hexafluorocyclopentene ring is disordered in the ratio of 50 : 50. The N-H proton in the imidazoline ring occupies the two sites (H51 and H52) on the nitrogen atoms in the ratio of 50 : 50. After irradiation with visible light, the residual electron density peaks for the sulfur and carbon atoms of 1c disappeared. ; _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^)+(0.0676P)^2^+3.7425P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3036 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.1600 _refine_ls_wR_factor_gt 0.1573 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _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 0.7183(2) 0.05679(8) 0.1571(3) 0.0273(6) Uani 1 1 d . . . C2 C 0.7939(2) 0.05144(8) 0.2736(3) 0.0233(5) Uani 1 1 d . A . C3 C 0.8984(2) 0.07945(8) 0.2663(3) 0.0242(5) Uani 1 1 d . . . H3 H 0.9590 0.0800 0.3387 0.029 Uiso 1 1 calc R . . C4 C 0.9028(2) 0.10530(8) 0.1456(3) 0.0259(5) Uani 1 1 d . . . C5 C 0.7709(2) 0.02124(8) 0.3944(3) 0.0257(5) Uani 1 1 d . . . C7 C 0.7500 0.0000 0.6442(4) 0.0359(9) Uani 1 2 d S . . C8 C 0.5990(2) 0.03569(9) 0.1244(3) 0.0347(6) Uani 1 1 d . . . H8A H 0.6113 0.0095 0.0627 0.052 Uiso 1 1 calc R . . H8B H 0.5472 0.0573 0.0747 0.052 Uiso 1 1 calc R . . H8C H 0.5602 0.0264 0.2144 0.052 Uiso 1 1 calc R . . C9 C 0.9920(2) 0.13936(8) 0.1055(3) 0.0279(6) Uani 1 1 d . . . C10 C 1.0798(3) 0.15259(9) 0.2041(3) 0.0351(6) Uani 1 1 d . . . H10 H 1.0845 0.1383 0.2953 0.042 Uiso 1 1 calc R . . C11 C 1.1600(3) 0.18636(9) 0.1699(4) 0.0410(7) Uani 1 1 d . . . H11 H 1.2193 0.1949 0.2387 0.049 Uiso 1 1 calc R . . C12 C 1.1566(3) 0.20790(9) 0.0395(4) 0.0402(8) Uani 1 1 d . . . C13 C 1.0708(3) 0.19457(11) -0.0585(4) 0.0502(9) Uani 1 1 d . . . H13 H 1.0668 0.2090 -0.1496 0.060 Uiso 1 1 calc R . . C14 C 0.9896(3) 0.16038(10) -0.0269(4) 0.0414(7) Uani 1 1 d . . . H14 H 0.9321 0.1514 -0.0971 0.050 Uiso 1 1 calc R . . C15 C 1.2413(3) 0.24549(11) 0.0083(5) 0.0574(10) Uani 1 1 d . . . C16 C 1.3887(4) 0.29638(12) 0.0313(6) 0.0773(15) Uani 1 1 d . . . H16A H 1.4774 0.2922 0.0266 0.093 Uiso 1 1 calc R . . H16B H 1.3708 0.3237 0.0878 0.093 Uiso 1 1 calc R . . C6A C 0.7742(7) 0.0407(2) 0.5455(7) 0.0292(16) Uiso 0.50 1 d P A 1 F1A F 0.6884(5) 0.07178(13) 0.5690(4) 0.0477(9) Uani 0.50 1 d P A 1 F2A F 0.8805(4) 0.05935(16) 0.5780(4) 0.0468(10) Uani 0.50 1 d P A 1 C6B C 0.8098(7) 0.0342(2) 0.5448(7) 0.0320(17) Uiso 0.50 1 d P A 2 F1B F 0.7739(5) 0.07709(12) 0.5750(4) 0.0502(11) Uani 0.50 1 d P A 2 F2B F 0.9315(4) 0.03398(17) 0.5630(4) 0.0477(10) Uani 0.50 1 d P A 2 C17 C 1.3359(6) 0.29920(18) -0.1141(7) 0.109(2) Uani 1 1 d . . . H17A H 1.3946 0.2889 -0.1875 0.131 Uiso 1 1 calc R . . H17B H 1.3119 0.3303 -0.1366 0.131 Uiso 1 1 calc R . . F3 F 0.6447(4) 0.01697(17) 0.6935(5) 0.0485(11) Uani 0.50 1 d P . . F4 F 0.8181(5) -0.00948(18) 0.7591(5) 0.0516(12) Uani 0.50 1 d P . . N1 N 1.3292(3) 0.25706(10) 0.0941(6) 0.0642(11) Uani 1 1 d . . . N2 N 1.2291(3) 0.26962(12) -0.1107(5) 0.0756(11) Uani 1 1 d . . . S1 S 0.77631(6) 0.09578(2) 0.04002(7) 0.0312(2) Uani 1 1 d . . . H52 H 1.243(6) 0.249(2) -0.179(6) 0.037(19) Uiso 0.50 1 d P . . H51 H 1.326(7) 0.253(3) 0.174(7) 0.04(2) Uiso 0.50 1 d P . . 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 0.0246(13) 0.0226(12) 0.0348(14) 0.0031(10) 0.0019(11) 0.0014(10) C2 0.0214(11) 0.0191(11) 0.0295(13) -0.0024(9) 0.0032(10) 0.0011(9) C3 0.0238(12) 0.0184(11) 0.0306(12) -0.0032(10) 0.0031(10) -0.0002(9) C4 0.0237(12) 0.0181(11) 0.0359(13) -0.0024(10) 0.0048(11) 0.0037(9) C5 0.0232(12) 0.0268(12) 0.0271(12) -0.0023(10) 0.0007(10) -0.0025(9) C7 0.035(2) 0.047(2) 0.0258(18) 0.000 0.000 -0.0083(18) C8 0.0247(13) 0.0341(14) 0.0452(16) 0.0105(12) -0.0094(12) -0.0033(11) C9 0.0230(12) 0.0187(11) 0.0421(14) 0.0008(10) 0.0113(11) 0.0039(9) C10 0.0401(15) 0.0257(13) 0.0395(15) -0.0038(11) 0.0116(13) -0.0069(11) C11 0.0368(16) 0.0305(14) 0.0558(18) -0.0089(13) 0.0140(14) -0.0086(12) C12 0.0284(15) 0.0224(13) 0.070(2) 0.0057(13) 0.0191(14) 0.0035(11) C13 0.0361(16) 0.0439(17) 0.071(2) 0.0331(17) 0.0118(16) 0.0051(14) C14 0.0258(14) 0.0409(16) 0.0573(19) 0.0199(14) 0.0028(13) 0.0025(12) C15 0.0410(19) 0.0288(15) 0.102(3) 0.0103(18) 0.035(2) 0.0015(14) C16 0.045(2) 0.0374(18) 0.150(5) 0.008(2) 0.038(3) -0.0098(16) F1A 0.062(3) 0.037(2) 0.044(2) -0.0136(16) 0.011(2) 0.004(2) F2A 0.050(3) 0.056(3) 0.035(2) -0.0074(19) -0.0059(19) -0.031(2) F1B 0.081(3) 0.031(2) 0.039(2) -0.0114(15) 0.012(2) -0.012(2) F2B 0.037(2) 0.073(3) 0.0331(19) 0.003(2) -0.0078(17) -0.027(2) C17 0.131(5) 0.082(3) 0.115(4) 0.018(3) 0.046(4) -0.062(3) F3 0.044(3) 0.055(3) 0.046(3) -0.007(2) 0.017(2) -0.012(2) F4 0.059(3) 0.064(3) 0.031(2) 0.009(2) -0.013(2) -0.024(2) N1 0.0346(16) 0.0281(15) 0.130(4) 0.004(2) 0.021(2) -0.0072(11) N2 0.072(2) 0.0480(19) 0.107(3) 0.035(2) 0.031(2) -0.0126(17) S1 0.0272(4) 0.0291(4) 0.0375(4) 0.0107(3) -0.0015(3) -0.0003(3) _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 1.377(4) . ? C1 C8 1.494(3) . ? C1 S1 1.719(3) . ? C2 C3 1.429(3) . ? C2 C5 1.463(3) . ? C3 C4 1.363(4) . ? C3 H3 0.9500 . ? C4 C9 1.466(3) . ? C4 S1 1.732(3) . ? C5 C5 1.352(5) 2_655 ? C5 C6B 1.513(7) . ? C5 C6A 1.520(7) . ? C7 F4 1.337(6) 2_655 ? C7 F4 1.337(6) . ? C7 F3 1.351(5) 2_655 ? C7 F3 1.351(5) . ? C7 C6B 1.529(7) . ? C7 C6B 1.529(7) 2_655 ? C7 C6A 1.547(7) . ? C7 C6A 1.547(7) 2_655 ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.382(4) . ? C9 C10 1.392(4) . ? C10 C11 1.382(4) . ? C10 H10 0.9500 . ? C11 C12 1.373(4) . ? C11 H11 0.9500 . ? C12 C13 1.374(5) . ? C12 C15 1.491(4) . ? C13 C14 1.392(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 N1 1.304(6) . ? C15 N2 1.327(5) . ? C16 N1 1.469(5) . ? C16 C17 1.474(8) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C6A F2A 1.336(8) . ? C6A F1A 1.347(9) . ? C6B F2B 1.357(9) . ? C6B F1B 1.371(8) . ? C17 N2 1.476(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? F3 F4 0.769(5) 2_655 ? F4 F3 0.769(5) 2_655 ? F4 F4 1.610(11) 2_655 ? N1 H51 0.75(6) . ? N2 H52 0.91(7) . ? 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 C8 130.3(2) . . ? C2 C1 S1 110.45(18) . . ? C8 C1 S1 119.2(2) . . ? C1 C2 C3 112.7(2) . . ? C1 C2 C5 124.7(2) . . ? C3 C2 C5 122.6(2) . . ? C4 C3 C2 113.6(2) . . ? C4 C3 H3 123.2 . . ? C2 C3 H3 123.2 . . ? C3 C4 C9 128.9(2) . . ? C3 C4 S1 110.09(18) . . ? C9 C4 S1 120.9(2) . . ? C5 C5 C2 129.78(13) 2_655 . ? C5 C5 C6B 109.8(3) 2_655 . ? C2 C5 C6B 120.0(3) . . ? C5 C5 C6A 111.6(3) 2_655 . ? C2 C5 C6A 117.9(3) . . ? F4 C7 F4 74.1(5) 2_655 . ? F4 C7 F3 107.2(5) 2_655 2_655 ? F4 C7 F3 107.2(5) . . ? F3 C7 F3 140.4(5) 2_655 . ? F4 C7 C6B 125.7(4) 2_655 . ? F4 C7 C6B 112.4(4) . . ? F3 C7 C6B 94.8(4) 2_655 . ? F3 C7 C6B 109.0(4) . . ? F4 C7 C6B 112.4(4) 2_655 2_655 ? F4 C7 C6B 125.7(4) . 2_655 ? F3 C7 C6B 109.0(4) 2_655 2_655 ? F3 C7 C6B 94.8(4) . 2_655 ? C6B C7 C6B 105.7(5) . 2_655 ? F4 C7 C6A 113.8(4) 2_655 . ? F4 C7 C6A 122.9(3) . . ? F3 C7 C6A 110.3(3) 2_655 . ? F3 C7 C6A 93.1(4) . . ? C6B C7 C6A 104.1(3) 2_655 . ? F4 C7 C6A 122.9(3) 2_655 2_655 ? F4 C7 C6A 113.8(4) . 2_655 ? F3 C7 C6A 93.1(4) 2_655 2_655 ? F3 C7 C6A 110.3(3) . 2_655 ? C6B C7 C6A 104.1(3) . 2_655 ? C6A C7 C6A 107.3(5) . 2_655 ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 118.0(2) . . ? C14 C9 C4 122.0(3) . . ? C10 C9 C4 120.0(2) . . ? C11 C10 C9 120.3(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 121.9(3) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 117.9(3) . . ? C11 C12 C15 120.5(3) . . ? C13 C12 C15 121.6(3) . . ? C12 C13 C14 121.2(3) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C9 C14 C13 120.7(3) . . ? C9 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? N1 C15 N2 116.1(3) . . ? N1 C15 C12 123.3(4) . . ? N2 C15 C12 120.5(4) . . ? N1 C16 C17 103.4(4) . . ? N1 C16 H16A 111.1 . . ? C17 C16 H16A 111.1 . . ? N1 C16 H16B 111.1 . . ? C17 C16 H16B 111.1 . . ? H16A C16 H16B 109.0 . . ? F2A C6A F1A 107.2(6) . . ? F2A C6A C5 112.9(5) . . ? F1A C6A C5 113.4(5) . . ? F2A C6A C7 110.3(5) . . ? F1A C6A C7 109.0(5) . . ? C5 C6A C7 104.1(4) . . ? F2B C6B F1B 105.5(6) . . ? F2B C6B C5 113.3(5) . . ? F1B C6B C5 110.3(5) . . ? F2B C6B C7 110.5(5) . . ? F1B C6B C7 112.1(5) . . ? C5 C6B C7 105.3(4) . . ? C16 C17 N2 105.2(4) . . ? C16 C17 H17A 110.7 . . ? N2 C17 H17A 110.7 . . ? C16 C17 H17B 110.7 . . ? N2 C17 H17B 110.7 . . ? H17A C17 H17B 108.8 . . ? F4 F3 C7 72.4(6) 2_655 . ? F3 F4 C7 74.4(5) 2_655 . ? F3 F4 F4 127.1(6) 2_655 2_655 ? C7 F4 F4 53.0(3) . 2_655 ? C15 N1 C16 107.7(4) . . ? C15 N1 H51 122(6) . . ? C16 N1 H51 122(6) . . ? C15 N2 C17 105.3(4) . . ? C15 N2 H52 101(4) . . ? C17 N2 H52 105(4) . . ? C1 S1 C4 93.13(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.685 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.069