# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_section_title ; Photochromism of Single Crystals Composed of Dioxazolylethene and Dithiazolylethene ; _publ_section_abstract ' ' _publ_contact_author_name 'Masahiro Irie' _publ_contact_author_address ; Dept. of Chemistry & Biochemistry Kyushu University Graduate School of Engineering 6-10-1 Hakozaki Higashi-ku Fukuoka 812-8581 JAPAN ; _publ_contact_author_phone ' 81(92)6423556 ' _publ_contact_author_fax ' 81(92)6423568 ' _publ_contact_author_email irie@cstf.kyushu-u.ac.jp loop_ _publ_author_name _publ_author_address 'Lumi Kuroki' ;Department of Chemistry and Biochemistry Graduate School of Engineering, Kyushu University Hakozaki 6-10-1, Higashi-ku, Fukuoka, Japan ; 'Shizuka Takami' ;Department of Chemistry and Biochemistry Graduate School of Engineering, Kyushu University Hakozaki 6-10-1, Higashi-ku, Fukuoka 812-8581, Japan ; 'Katsunori Shibata' ;Department of Chemistry and Biochemistry Graduate School of Engineering, Kyushu University Hakozaki 6-10-1, Higashi-ku, Fukuoka 812-8581, Japan ; 'Masahiro Irie' ;Department of Chemistry and Biochemistry Graduate School of Engineering, Kyushu University Hakozaki 6-10-1, Higashi-ku, Fukuoka 812-8581, Japan ; data_2a _database_code_depnum_ccdc_archive 'CCDC 282860' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1,2-bis(5-methyl-2-phenyl-4-thiazolyl)perfluorocyclopentene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H16 F6 N2 S2' _chemical_formula_weight 522.52 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.236(2) _cell_length_b 25.752(8) _cell_length_c 12.611(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.432(5) _cell_angle_gamma 90.00 _cell_volume 2295.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 935 _cell_measurement_theta_min 2.289 _cell_measurement_theta_max 27.298 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.298 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.707363 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'sadabs sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 detactor' _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_% 1.6 _diffrn_reflns_number 11529 _diffrn_reflns_av_R_equivalents 0.0944 _diffrn_reflns_av_sigmaI/netI 0.1092 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.26 _reflns_number_total 4662 _reflns_number_gt 2752 _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^)+(0.0762P)^2^+0.0000P] 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 calculated _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4662 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1149 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1530 _refine_ls_wR_factor_gt 0.1261 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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 0.1214(5) 0.27327(14) 0.7034(3) 0.0219(8) Uani 1 1 d . . . C2 C 0.2178(5) 0.30304(13) 0.7876(3) 0.0185(8) Uani 1 1 d . . . C3 C 0.1466(4) 0.35109(14) 0.8249(3) 0.0186(8) Uani 1 1 d . . . C4 C 0.1481(5) 0.36046(14) 0.9438(3) 0.0245(8) Uani 1 1 d . . . C5 C 0.0806(5) 0.41659(15) 0.9477(3) 0.0272(9) Uani 1 1 d . . . C6 C -0.0274(5) 0.42716(14) 0.8314(3) 0.0225(8) Uani 1 1 d . . . C7 C 0.0630(4) 0.39110(14) 0.7644(3) 0.0180(8) Uani 1 1 d . . . C8 C 0.0604(5) 0.40133(13) 0.6498(3) 0.0181(8) Uani 1 1 d . . . C9 C 0.2139(4) 0.39616(13) 0.6036(3) 0.0170(7) Uani 1 1 d . . . C10 C -0.0729(5) 0.28024(16) 0.6325(3) 0.0315(9) Uani 1 1 d . . . H10A H -0.1512 0.3008 0.6713 0.047 Uiso 1 1 calc R . . H10B H -0.1314 0.2462 0.6143 0.047 Uiso 1 1 calc R . . H10C H -0.0626 0.2983 0.5656 0.047 Uiso 1 1 calc R . . C11 C 0.4127(5) 0.38059(15) 0.6536(3) 0.0246(9) Uani 1 1 d . . . H11A H 0.4407 0.3892 0.7311 0.037 Uiso 1 1 calc R . . H11B H 0.5003 0.3993 0.6178 0.037 Uiso 1 1 calc R . . H11C H 0.4274 0.3431 0.6446 0.037 Uiso 1 1 calc R . . C12 C 0.4393(5) 0.24284(14) 0.7906(3) 0.0225(8) Uani 1 1 d . . . C13 C 0.6232(5) 0.21727(14) 0.8193(3) 0.0226(8) Uani 1 1 d . . . C14 C 0.7551(5) 0.23401(14) 0.9106(3) 0.0261(9) Uani 1 1 d . . . H14 H 0.7216 0.2609 0.9546 0.031 Uiso 1 1 calc R . . C15 C 0.9321(5) 0.21237(15) 0.9379(3) 0.0313(10) Uani 1 1 d . . . H15 H 1.0203 0.2244 1.0000 0.038 Uiso 1 1 calc R . . C16 C 0.9825(6) 0.17286(16) 0.8748(3) 0.0352(10) Uani 1 1 d . . . H16 H 1.1048 0.1576 0.8939 0.042 Uiso 1 1 calc R . . C17 C 0.8544(6) 0.15584(15) 0.7842(3) 0.0348(10) Uani 1 1 d . . . H17 H 0.8888 0.1290 0.7406 0.042 Uiso 1 1 calc R . . C18 C 0.6757(6) 0.17775(15) 0.7566(3) 0.0297(9) Uani 1 1 d . . . H18 H 0.5881 0.1657 0.6943 0.036 Uiso 1 1 calc R . . C19 C -0.0788(4) 0.42541(13) 0.4828(3) 0.0172(7) Uani 1 1 d . . . C20 C -0.2258(4) 0.44298(13) 0.3895(3) 0.0166(7) Uani 1 1 d . . . C21 C -0.2020(5) 0.43729(15) 0.2837(3) 0.0270(9) Uani 1 1 d . . . H21 H -0.0906 0.4214 0.2706 0.032 Uiso 1 1 calc R . . C22 C -0.3397(5) 0.45470(16) 0.1973(3) 0.0305(9) Uani 1 1 d . . . H22 H -0.3226 0.4505 0.1252 0.037 Uiso 1 1 calc R . . C23 C -0.5008(5) 0.47795(14) 0.2153(3) 0.0234(8) Uani 1 1 d . . . H23 H -0.5939 0.4905 0.1559 0.028 Uiso 1 1 calc R . . C24 C -0.5273(5) 0.48301(14) 0.3210(3) 0.0241(8) Uani 1 1 d . . . H24 H -0.6396 0.4985 0.3339 0.029 Uiso 1 1 calc R . . C25 C -0.3900(5) 0.46544(13) 0.4068(3) 0.0217(8) Uani 1 1 d . . . H25 H -0.4086 0.4688 0.4788 0.026 Uiso 1 1 calc R . . F1 F 0.3199(3) 0.35369(9) 1.00984(15) 0.0388(6) Uani 1 1 d . . . F2 F 0.0277(3) 0.32842(9) 0.98070(16) 0.0408(6) Uani 1 1 d . . . F3 F -0.0198(3) 0.42485(10) 1.02323(17) 0.0464(7) Uani 1 1 d . . . F4 F 0.2332(3) 0.44863(9) 0.97062(17) 0.0413(6) Uani 1 1 d . . . F5 F -0.2135(3) 0.41559(8) 0.82364(16) 0.0312(5) Uani 1 1 d . . . F6 F -0.0220(3) 0.47789(8) 0.80506(16) 0.0313(5) Uani 1 1 d . . . N1 N 0.3960(4) 0.28524(11) 0.8373(2) 0.0217(7) Uani 1 1 d . . . N2 N -0.1058(4) 0.41854(11) 0.5813(2) 0.0172(6) Uani 1 1 d . . . S1 S 0.25942(14) 0.22120(4) 0.68490(7) 0.0259(3) Uani 1 1 d . . . S2 S 0.14986(12) 0.41276(4) 0.46903(7) 0.0218(2) Uani 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 0.0254(19) 0.023(2) 0.0155(17) 0.0036(16) 0.0003(15) -0.0012(16) C2 0.0256(19) 0.0175(18) 0.0109(16) 0.0007(15) 0.0010(14) 0.0019(15) C3 0.0180(17) 0.024(2) 0.0107(16) 0.0007(15) -0.0028(13) 0.0028(15) C4 0.031(2) 0.027(2) 0.0119(17) 0.0001(16) -0.0035(16) 0.0032(17) C5 0.032(2) 0.033(2) 0.0157(18) -0.0037(17) 0.0021(16) 0.0066(18) C6 0.0219(19) 0.025(2) 0.0185(18) 0.0000(16) -0.0009(15) 0.0030(16) C7 0.0150(17) 0.0216(19) 0.0145(17) -0.0020(15) -0.0032(14) 0.0000(15) C8 0.0210(18) 0.0187(19) 0.0122(17) -0.0019(14) -0.0018(14) 0.0014(15) C9 0.0173(17) 0.0179(18) 0.0142(17) 0.0001(14) -0.0002(14) -0.0013(15) C10 0.031(2) 0.032(2) 0.026(2) -0.0038(18) -0.0067(17) -0.0041(18) C11 0.0187(19) 0.032(2) 0.0212(19) 0.0020(17) 0.0008(15) -0.0010(16) C12 0.033(2) 0.022(2) 0.0124(17) 0.0024(16) 0.0036(15) 0.0015(16) C13 0.033(2) 0.0205(19) 0.0162(18) 0.0040(16) 0.0087(16) 0.0050(17) C14 0.033(2) 0.022(2) 0.0231(19) -0.0012(16) 0.0060(16) 0.0053(17) C15 0.027(2) 0.031(2) 0.035(2) 0.0079(19) 0.0032(17) 0.0065(18) C16 0.033(2) 0.028(2) 0.047(3) 0.016(2) 0.014(2) 0.0127(19) C17 0.051(3) 0.028(2) 0.032(2) 0.0079(19) 0.024(2) 0.014(2) C18 0.046(2) 0.027(2) 0.0179(19) 0.0049(17) 0.0131(17) 0.0068(19) C19 0.0184(17) 0.0166(18) 0.0155(17) 0.0005(15) 0.0011(14) 0.0002(14) C20 0.0195(17) 0.0156(18) 0.0121(16) 0.0013(14) -0.0019(14) -0.0034(15) C21 0.024(2) 0.042(2) 0.0145(18) 0.0019(17) 0.0029(15) 0.0035(18) C22 0.036(2) 0.042(2) 0.0125(18) 0.0044(18) 0.0022(16) -0.0002(19) C23 0.026(2) 0.025(2) 0.0146(17) 0.0038(16) -0.0060(15) -0.0005(16) C24 0.024(2) 0.027(2) 0.0190(18) -0.0040(16) -0.0016(15) 0.0057(16) C25 0.028(2) 0.023(2) 0.0130(17) 0.0015(15) 0.0007(15) 0.0093(16) F1 0.0428(14) 0.0496(15) 0.0148(11) -0.0073(10) -0.0139(9) 0.0188(12) F2 0.0673(16) 0.0384(15) 0.0190(11) -0.0014(11) 0.0148(11) -0.0107(12) F3 0.0618(16) 0.0605(18) 0.0186(12) -0.0036(12) 0.0123(11) 0.0245(13) F4 0.0499(15) 0.0325(13) 0.0296(12) -0.0070(11) -0.0176(10) -0.0055(12) F5 0.0198(11) 0.0437(14) 0.0289(12) -0.0046(11) 0.0026(9) 0.0037(10) F6 0.0417(13) 0.0246(12) 0.0247(11) -0.0017(10) 0.0004(10) 0.0045(10) N1 0.0279(17) 0.0211(17) 0.0138(14) 0.0032(13) -0.0008(12) 0.0077(14) N2 0.0177(15) 0.0202(16) 0.0125(14) -0.0002(12) 0.0006(12) 0.0001(13) S1 0.0374(6) 0.0221(5) 0.0154(4) -0.0023(4) -0.0009(4) 0.0005(4) S2 0.0188(4) 0.0299(5) 0.0159(4) 0.0029(4) 0.0022(3) 0.0010(4) _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 1.372(5) . ? C1 C10 1.506(5) . ? C1 S1 1.718(4) . ? C2 N1 1.385(4) . ? C2 C3 1.457(5) . ? C3 C7 1.345(5) . ? C3 C4 1.517(5) . ? C4 F1 1.350(4) . ? C4 F2 1.353(4) . ? C4 C5 1.530(5) . ? C5 F3 1.333(4) . ? C5 F4 1.358(4) . ? C5 C6 1.531(5) . ? C6 F6 1.351(4) . ? C6 F5 1.362(4) . ? C6 C7 1.498(5) . ? C7 C8 1.465(4) . ? C8 C9 1.367(5) . ? C8 N2 1.394(4) . ? C9 C11 1.496(4) . ? C9 S2 1.714(3) . ? C12 N1 1.311(4) . ? C12 C13 1.459(5) . ? C12 S1 1.742(3) . ? C13 C18 1.391(5) . ? C13 C14 1.396(5) . ? C14 C15 1.371(5) . ? C15 C16 1.388(5) . ? C16 C17 1.378(6) . ? C17 C18 1.385(5) . ? C19 N2 1.310(4) . ? C19 C20 1.477(4) . ? C19 S2 1.731(3) . ? C20 C25 1.381(5) . ? C20 C21 1.390(4) . ? C21 C22 1.383(5) . ? C22 C23 1.373(5) . ? C23 C24 1.394(5) . ? C24 C25 1.378(5) . ? 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 C10 130.3(3) . . ? C2 C1 S1 109.1(3) . . ? C10 C1 S1 120.5(3) . . ? C1 C2 N1 115.7(3) . . ? C1 C2 C3 124.6(3) . . ? N1 C2 C3 119.6(3) . . ? C7 C3 C2 127.9(3) . . ? C7 C3 C4 110.2(3) . . ? C2 C3 C4 121.8(3) . . ? F1 C4 F2 106.5(3) . . ? F1 C4 C3 113.5(3) . . ? F2 C4 C3 112.0(3) . . ? F1 C4 C5 111.1(3) . . ? F2 C4 C5 109.3(3) . . ? C3 C4 C5 104.4(3) . . ? F3 C5 F4 107.1(3) . . ? F3 C5 C4 113.6(3) . . ? F4 C5 C4 109.3(3) . . ? F3 C5 C6 114.3(3) . . ? F4 C5 C6 108.6(3) . . ? C4 C5 C6 103.8(3) . . ? F6 C6 F5 105.9(3) . . ? F6 C6 C7 114.9(3) . . ? F5 C6 C7 111.6(3) . . ? F6 C6 C5 111.9(3) . . ? F5 C6 C5 108.9(3) . . ? C7 C6 C5 103.6(3) . . ? C3 C7 C8 127.3(3) . . ? C3 C7 C6 110.6(3) . . ? C8 C7 C6 122.1(3) . . ? C9 C8 N2 116.0(3) . . ? C9 C8 C7 124.3(3) . . ? N2 C8 C7 119.7(3) . . ? C8 C9 C11 130.0(3) . . ? C8 C9 S2 109.0(2) . . ? C11 C9 S2 120.9(2) . . ? N1 C12 C13 123.9(3) . . ? N1 C12 S1 113.5(3) . . ? C13 C12 S1 122.5(3) . . ? C18 C13 C14 118.2(3) . . ? C18 C13 C12 122.4(3) . . ? C14 C13 C12 119.4(3) . . ? C15 C14 C13 121.1(4) . . ? C14 C15 C16 120.1(4) . . ? C17 C16 C15 119.7(4) . . ? C16 C17 C18 120.3(4) . . ? C17 C18 C13 120.7(4) . . ? N2 C19 C20 124.6(3) . . ? N2 C19 S2 114.3(2) . . ? C20 C19 S2 121.2(2) . . ? C25 C20 C21 119.0(3) . . ? C25 C20 C19 119.9(3) . . ? C21 C20 C19 121.1(3) . . ? C22 C21 C20 120.3(3) . . ? C23 C22 C21 120.3(3) . . ? C22 C23 C24 119.7(3) . . ? C25 C24 C23 119.7(3) . . ? C24 C25 C20 120.9(3) . . ? C12 N1 C2 111.2(3) . . ? C19 N2 C8 110.2(3) . . ? C1 S1 C12 90.39(17) . . ? C9 S2 C19 90.46(16) . . ? 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 C10 C1 C2 N1 179.3(3) . . . . ? S1 C1 C2 N1 -0.5(4) . . . . ? C10 C1 C2 C3 -1.7(6) . . . . ? S1 C1 C2 C3 178.5(3) . . . . ? C1 C2 C3 C7 -45.9(6) . . . . ? N1 C2 C3 C7 133.0(4) . . . . ? C1 C2 C3 C4 129.9(4) . . . . ? N1 C2 C3 C4 -51.2(5) . . . . ? C7 C3 C4 F1 -130.0(3) . . . . ? C2 C3 C4 F1 53.6(5) . . . . ? C7 C3 C4 F2 109.3(3) . . . . ? C2 C3 C4 F2 -67.2(4) . . . . ? C7 C3 C4 C5 -8.9(4) . . . . ? C2 C3 C4 C5 174.6(3) . . . . ? F1 C4 C5 F3 -90.5(4) . . . . ? F2 C4 C5 F3 26.8(4) . . . . ? C3 C4 C5 F3 146.9(3) . . . . ? F1 C4 C5 F4 29.1(4) . . . . ? F2 C4 C5 F4 146.4(3) . . . . ? C3 C4 C5 F4 -93.6(3) . . . . ? F1 C4 C5 C6 144.8(3) . . . . ? F2 C4 C5 C6 -97.8(3) . . . . ? C3 C4 C5 C6 22.2(4) . . . . ? F3 C5 C6 F6 84.4(4) . . . . ? F4 C5 C6 F6 -35.1(4) . . . . ? C4 C5 C6 F6 -151.3(3) . . . . ? F3 C5 C6 F5 -32.3(4) . . . . ? F4 C5 C6 F5 -151.8(3) . . . . ? C4 C5 C6 F5 92.0(3) . . . . ? F3 C5 C6 C7 -151.2(3) . . . . ? F4 C5 C6 C7 89.2(3) . . . . ? C4 C5 C6 C7 -27.0(4) . . . . ? C2 C3 C7 C8 -14.6(6) . . . . ? C4 C3 C7 C8 169.1(3) . . . . ? C2 C3 C7 C6 167.2(3) . . . . ? C4 C3 C7 C6 -9.0(4) . . . . ? F6 C6 C7 C3 145.4(3) . . . . ? F5 C6 C7 C3 -94.0(3) . . . . ? C5 C6 C7 C3 23.0(4) . . . . ? F6 C6 C7 C8 -32.9(4) . . . . ? F5 C6 C7 C8 87.8(4) . . . . ? C5 C6 C7 C8 -155.2(3) . . . . ? C3 C7 C8 C9 -42.9(5) . . . . ? C6 C7 C8 C9 135.0(4) . . . . ? C3 C7 C8 N2 138.5(4) . . . . ? C6 C7 C8 N2 -43.6(5) . . . . ? N2 C8 C9 C11 177.7(3) . . . . ? C7 C8 C9 C11 -1.0(6) . . . . ? N2 C8 C9 S2 -0.5(4) . . . . ? C7 C8 C9 S2 -179.2(3) . . . . ? N1 C12 C13 C18 -168.9(3) . . . . ? S1 C12 C13 C18 7.8(5) . . . . ? N1 C12 C13 C14 8.7(5) . . . . ? S1 C12 C13 C14 -174.6(3) . . . . ? C18 C13 C14 C15 0.3(6) . . . . ? C12 C13 C14 C15 -177.4(3) . . . . ? C13 C14 C15 C16 -0.5(6) . . . . ? C14 C15 C16 C17 0.5(6) . . . . ? C15 C16 C17 C18 -0.4(6) . . . . ? C16 C17 C18 C13 0.3(6) . . . . ? C14 C13 C18 C17 -0.2(5) . . . . ? C12 C13 C18 C17 177.4(3) . . . . ? N2 C19 C20 C25 16.0(5) . . . . ? S2 C19 C20 C25 -163.3(3) . . . . ? N2 C19 C20 C21 -164.0(3) . . . . ? S2 C19 C20 C21 16.8(5) . . . . ? C25 C20 C21 C22 1.1(5) . . . . ? C19 C20 C21 C22 -179.0(3) . . . . ? C20 C21 C22 C23 0.2(6) . . . . ? C21 C22 C23 C24 -1.3(6) . . . . ? C22 C23 C24 C25 1.1(5) . . . . ? C23 C24 C25 C20 0.2(6) . . . . ? C21 C20 C25 C24 -1.3(5) . . . . ? C19 C20 C25 C24 178.7(3) . . . . ? C13 C12 N1 C2 175.0(3) . . . . ? S1 C12 N1 C2 -1.9(4) . . . . ? C1 C2 N1 C12 1.6(4) . . . . ? C3 C2 N1 C12 -177.4(3) . . . . ? C20 C19 N2 C8 179.4(3) . . . . ? S2 C19 N2 C8 -1.3(4) . . . . ? C9 C8 N2 C19 1.2(4) . . . . ? C7 C8 N2 C19 179.9(3) . . . . ? C2 C1 S1 C12 -0.5(3) . . . . ? C10 C1 S1 C12 179.7(3) . . . . ? N1 C12 S1 C1 1.4(3) . . . . ? C13 C12 S1 C1 -175.5(3) . . . . ? C8 C9 S2 C19 -0.2(3) . . . . ? C11 C9 S2 C19 -178.6(3) . . . . ? N2 C19 S2 C9 0.9(3) . . . . ? C20 C19 S2 C9 -179.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 27.26 _diffrn_measured_fraction_theta_full 0.907 _refine_diff_density_max 0.449 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.091 #===END data_Mixed _database_code_depnum_ccdc_archive 'CCDC 282861' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Mixed crystal of dioxazolylethene and dithiazolylethene' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H32 F12 N4 O2 S2' _chemical_formula_weight 1012.92 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' 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.202(2) _cell_length_b 25.771(7) _cell_length_c 12.589(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.302(4) _cell_angle_gamma 90.00 _cell_volume 2282.7(11) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 845 _cell_measurement_theta_min 3.000 _cell_measurement_theta_max 21.426 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.884726 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'sadabs sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 are 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_% 0.0061 _diffrn_reflns_number 12804 _diffrn_reflns_av_R_equivalents 0.0638 _diffrn_reflns_av_sigmaI/netI 0.1084 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4782 _reflns_number_gt 2478 _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^)+(0.0707P)^2^+0.0000P] 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 calculated _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4782 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1306 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1530 _refine_ls_wR_factor_gt 0.1268 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 0.2842(5) 0.10363(13) 0.8973(3) 0.0286(9) Uani 1 1 d . . . C2 C 0.4378(5) 0.09832(13) 0.8500(3) 0.0254(8) Uani 1 1 d . A . C4 C 0.5778(5) 0.07426(13) 1.0153(3) 0.0255(8) Uani 1 1 d . . . C5 C 0.4316(5) 0.10793(14) 0.7348(3) 0.0272(8) Uani 1 1 d . . . C6 C 0.5245(5) 0.07269(14) 0.6681(3) 0.0317(9) Uani 1 1 d . A . C7 C 0.4149(6) 0.08172(16) 0.5516(3) 0.0405(10) Uani 1 1 d . . . C8 C 0.3405(5) 0.13752(15) 0.5548(3) 0.0327(9) Uani 1 1 d . A . C9 C 0.3442(5) 0.14729(14) 0.6727(3) 0.0286(9) Uani 1 1 d . A . C10 C 0.3609(5) 0.22531(14) 0.7937(3) 0.0288(9) Uani 1 1 d . . . C11 C 0.2690(5) 0.19539(14) 0.7098(3) 0.0275(8) Uani 1 1 d . A . C13 C 0.0465(5) 0.25485(14) 0.7059(3) 0.0302(9) Uani 1 1 d . . . C14 C 0.0837(5) 0.11867(14) 0.8508(3) 0.0386(10) Uani 1 1 d . A . H14A H 0.0679 0.1551 0.8616 0.058 Uiso 1 1 calc R . . H14B H 0.0003 0.0995 0.8864 0.058 Uiso 1 1 calc R . . H14C H 0.0536 0.1111 0.7744 0.058 Uiso 1 1 calc R . . C15 C 0.5539(5) 0.21985(15) 0.8661(3) 0.0377(10) Uani 1 1 d . A . H15A H 0.5428 0.2028 0.9323 0.057 Uiso 1 1 calc R . . H15B H 0.6090 0.2536 0.8825 0.057 Uiso 1 1 calc R . . H15C H 0.6337 0.1996 0.8299 0.057 Uiso 1 1 calc R . . C16 C 0.7200(5) 0.05696(12) 1.1093(3) 0.0233(8) Uani 1 1 d . A . C17 C 0.8864(5) 0.03411(13) 1.0936(3) 0.0269(8) Uani 1 1 d . . . H17 H 0.9063 0.0304 1.0233 0.032 Uiso 1 1 calc R A . C18 C 1.0220(5) 0.01685(13) 1.1800(3) 0.0319(9) Uani 1 1 d . A . H18 H 1.1320 0.0012 1.1679 0.038 Uiso 1 1 calc R . . C19 C 0.9961(5) 0.02264(14) 1.2848(3) 0.0337(9) Uani 1 1 d . . . H19 H 1.0875 0.0105 1.3432 0.040 Uiso 1 1 calc R A . C20 C 0.8356(6) 0.04636(16) 1.3026(3) 0.0427(11) Uani 1 1 d . A . H20 H 0.8193 0.0511 1.3732 0.051 Uiso 1 1 calc R . . C21 C 0.6967(5) 0.06340(15) 1.2152(3) 0.0353(9) Uani 1 1 d . . . H21 H 0.5874 0.0792 1.2278 0.042 Uiso 1 1 calc R A . C22 C -0.1372(6) 0.28091(14) 0.6777(3) 0.0334(9) Uani 1 1 d . A . C23 C -0.2699(5) 0.26356(15) 0.5886(3) 0.0398(10) Uani 1 1 d . . . H23 H -0.2389 0.2365 0.5467 0.048 Uiso 1 1 calc R A . C24 C -0.4471(6) 0.28590(17) 0.5612(4) 0.0519(12) Uani 1 1 d . A . H24 H -0.5334 0.2737 0.5006 0.062 Uiso 1 1 calc R . . C25 C -0.4988(7) 0.32495(19) 0.6196(5) 0.0628(14) Uani 1 1 d . . . H25 H -0.6195 0.3394 0.5994 0.075 Uiso 1 1 calc R A . C26 C -0.3744(7) 0.34316(16) 0.7081(4) 0.0536(13) Uani 1 1 d . A . H26 H -0.4104 0.3701 0.7485 0.064 Uiso 1 1 calc R . . C27 C -0.1896(7) 0.32140(15) 0.7396(3) 0.0517(13) Uani 1 1 d . . . H27 H -0.1045 0.3339 0.8004 0.062 Uiso 1 1 calc R A . F1 F 0.7108(3) 0.08500(9) 0.67536(17) 0.0437(6) Uani 1 1 d . . . F2 F 0.5254(3) 0.02199(8) 0.69546(18) 0.0458(6) Uani 1 1 d . . . F3 F 0.5151(4) 0.07415(10) 0.47538(19) 0.0639(8) Uani 1 1 d . A . F4 F 0.2664(3) 0.04852(9) 0.52978(18) 0.0584(7) Uani 1 1 d . A . F5 F 0.4545(4) 0.17061(9) 0.51486(18) 0.0567(7) Uani 1 1 d . . . F6 F 0.1678(3) 0.14202(9) 0.48962(17) 0.0529(7) Uani 1 1 d . . . N3 N 0.6039(4) 0.08086(10) 0.9172(2) 0.0268(7) Uani 1 1 d . A . N12 N 0.0901(4) 0.21268(11) 0.6590(2) 0.0296(7) Uani 1 1 d . A . S1 S 0.34510(18) 0.08778(4) 1.03224(10) 0.0257(4) Uiso 0.846(5) 1 d P A 1 S2 S 0.22172(17) 0.27834(6) 0.81159(10) 0.0306(4) Uiso 0.846(5) 1 d P A 1 O1 O 0.418(4) 0.0797(9) 1.004(2) 0.063(6) Uiso 0.154(5) 1 d P A 2 O2 O 0.215(3) 0.2536(12) 0.789(2) 0.068(7) Uiso 0.154(5) 1 d P A 2 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) 0.026(2) 0.0224(19) 0.0018(15) 0.0022(17) -0.0058(17) C2 0.0239(19) 0.024(2) 0.0237(19) 0.0027(15) -0.0049(16) -0.0040(15) C4 0.022(2) 0.028(2) 0.025(2) 0.0015(16) 0.0017(16) -0.0042(15) C5 0.0203(19) 0.033(2) 0.026(2) -0.0011(17) 0.0003(16) -0.0035(16) C6 0.026(2) 0.034(2) 0.032(2) 0.0050(17) -0.0009(17) 0.0006(17) C7 0.034(2) 0.056(3) 0.029(2) -0.005(2) 0.0001(19) 0.007(2) C8 0.031(2) 0.043(2) 0.020(2) 0.0034(17) -0.0055(17) 0.0046(19) C9 0.025(2) 0.039(2) 0.0204(19) 0.0015(17) 0.0015(16) 0.0003(17) C10 0.031(2) 0.032(2) 0.0227(19) 0.0077(17) 0.0051(17) 0.0002(18) C11 0.026(2) 0.036(2) 0.0193(19) 0.0056(16) 0.0034(16) 0.0029(17) C13 0.036(2) 0.033(2) 0.0215(19) 0.0038(17) 0.0076(18) -0.0065(18) C14 0.033(2) 0.039(2) 0.046(3) 0.0016(19) 0.015(2) -0.0043(18) C15 0.041(2) 0.037(2) 0.030(2) -0.0011(18) -0.0039(18) -0.0020(19) C16 0.0260(19) 0.0201(19) 0.0236(19) -0.0001(15) 0.0047(16) -0.0014(15) C17 0.034(2) 0.029(2) 0.0183(19) 0.0000(15) 0.0060(16) 0.0047(16) C18 0.034(2) 0.030(2) 0.027(2) -0.0011(17) -0.0030(17) 0.0074(17) C19 0.037(2) 0.039(2) 0.020(2) 0.0006(17) -0.0073(17) 0.0000(19) C20 0.046(3) 0.062(3) 0.021(2) 0.0036(19) 0.009(2) -0.004(2) C21 0.033(2) 0.049(2) 0.026(2) -0.0008(18) 0.0112(18) 0.0014(19) C22 0.044(2) 0.029(2) 0.031(2) 0.0097(18) 0.0168(19) 0.0083(19) C23 0.038(2) 0.037(2) 0.046(3) 0.0094(19) 0.013(2) 0.0145(19) C24 0.043(3) 0.043(3) 0.070(3) 0.015(2) 0.012(2) 0.016(2) C25 0.059(3) 0.057(3) 0.078(4) 0.028(3) 0.027(3) 0.013(3) C26 0.077(4) 0.028(2) 0.071(3) 0.017(2) 0.050(3) 0.026(2) C27 0.091(4) 0.035(3) 0.037(2) 0.008(2) 0.032(3) 0.002(2) F1 0.0260(12) 0.0633(16) 0.0404(14) 0.0008(11) 0.0039(10) 0.0068(11) F2 0.0525(15) 0.0383(14) 0.0421(14) -0.0034(11) 0.0000(11) 0.0047(11) F3 0.0760(19) 0.084(2) 0.0335(14) 0.0014(13) 0.0148(13) 0.0344(15) F4 0.0604(17) 0.0574(17) 0.0432(15) -0.0075(12) -0.0210(13) -0.0042(14) F5 0.080(2) 0.0608(17) 0.0327(14) 0.0030(12) 0.0204(13) -0.0124(14) F6 0.0465(15) 0.0760(18) 0.0264(13) -0.0082(11) -0.0142(11) 0.0200(13) N3 0.0265(17) 0.0288(18) 0.0219(16) 0.0048(13) -0.0023(13) -0.0038(13) N12 0.0288(18) 0.0366(19) 0.0219(16) 0.0084(14) 0.0020(14) 0.0056(14) _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 1.370(5) . ? C1 C14 1.489(5) . ? C1 O1 1.60(2) . ? C1 S1 1.711(4) . ? C2 N3 1.385(4) . ? C2 C5 1.462(5) . ? C4 O1 1.14(3) . ? C4 N3 1.300(4) . ? C4 C16 1.460(5) . ? C4 S1 1.769(4) . ? C5 C9 1.351(5) . ? C5 C6 1.489(5) . ? C6 F2 1.351(4) . ? C6 F1 1.363(4) . ? C6 C7 1.528(5) . ? C7 F3 1.332(4) . ? C7 F4 1.352(4) . ? C7 C8 1.538(5) . ? C8 F6 1.341(4) . ? C8 F5 1.353(4) . ? C8 C9 1.500(5) . ? C9 C11 1.468(5) . ? C10 O2 1.27(3) . ? C10 C11 1.360(5) . ? C10 C15 1.498(5) . ? C10 S2 1.738(4) . ? C11 N12 1.384(4) . ? C11 O2 1.89(3) . ? C13 N12 1.307(4) . ? C13 O2 1.42(2) . ? C13 C22 1.458(5) . ? C13 S2 1.736(4) . ? C16 C17 1.387(5) . ? C16 C21 1.388(5) . ? C17 C18 1.373(5) . ? C18 C19 1.379(5) . ? C19 C20 1.367(5) . ? C20 C21 1.391(5) . ? C22 C23 1.384(5) . ? C22 C27 1.401(5) . ? C23 C24 1.375(5) . ? C24 C25 1.345(6) . ? C25 C26 1.356(6) . ? C26 C27 1.421(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 C14 131.4(3) . . ? C2 C1 O1 85.8(12) . . ? C14 C1 O1 142.3(12) . . ? C2 C1 S1 110.3(3) . . ? C14 C1 S1 118.3(3) . . ? O1 C1 S1 25.1(12) . . ? C1 C2 N3 116.1(3) . . ? C1 C2 C5 123.8(3) . . ? N3 C2 C5 120.0(3) . . ? O1 C4 N3 102.0(13) . . ? O1 C4 C16 131.1(13) . . ? N3 C4 C16 126.3(3) . . ? O1 C4 S1 14.6(13) . . ? N3 C4 S1 114.9(3) . . ? C16 C4 S1 118.8(3) . . ? C9 C5 C2 127.8(3) . . ? C9 C5 C6 110.0(3) . . ? C2 C5 C6 122.2(3) . . ? F2 C6 F1 104.9(3) . . ? F2 C6 C5 115.1(3) . . ? F1 C6 C5 112.0(3) . . ? F2 C6 C7 111.4(3) . . ? F1 C6 C7 109.2(3) . . ? C5 C6 C7 104.3(3) . . ? F3 C7 F4 106.7(3) . . ? F3 C7 C6 114.9(3) . . ? F4 C7 C6 108.8(3) . . ? F3 C7 C8 113.7(3) . . ? F4 C7 C8 109.4(3) . . ? C6 C7 C8 103.2(3) . . ? F6 C8 F5 105.9(3) . . ? F6 C8 C9 114.2(3) . . ? F5 C8 C9 112.2(3) . . ? F6 C8 C7 110.3(3) . . ? F5 C8 C7 109.7(3) . . ? C9 C8 C7 104.5(3) . . ? C5 C9 C11 127.4(3) . . ? C5 C9 C8 110.7(3) . . ? C11 C9 C8 121.8(3) . . ? O2 C10 C11 91.6(14) . . ? O2 C10 C15 137.2(14) . . ? C11 C10 C15 130.9(3) . . ? O2 C10 S2 20.0(14) . . ? C11 C10 S2 110.4(3) . . ? C15 C10 S2 118.7(3) . . ? C10 C11 N12 115.3(3) . . ? C10 C11 C9 125.0(3) . . ? N12 C11 C9 119.6(3) . . ? C10 C11 O2 42.3(8) . . ? N12 C11 O2 73.2(8) . . ? C9 C11 O2 166.2(8) . . ? N12 C13 O2 93.7(13) . . ? N12 C13 C22 124.4(3) . . ? O2 C13 C22 140.9(13) . . ? N12 C13 S2 115.5(3) . . ? O2 C13 S2 22.8(13) . . ? C22 C13 S2 120.0(3) . . ? C17 C16 C21 118.2(3) . . ? C17 C16 C4 119.5(3) . . ? C21 C16 C4 122.3(3) . . ? C18 C17 C16 121.0(3) . . ? C17 C18 C19 120.4(3) . . ? C20 C19 C18 119.7(3) . . ? C19 C20 C21 120.2(3) . . ? C16 C21 C20 120.5(4) . . ? C23 C22 C27 118.0(4) . . ? C23 C22 C13 118.9(3) . . ? C27 C22 C13 123.0(4) . . ? C24 C23 C22 120.8(4) . . ? C25 C24 C23 121.8(5) . . ? C24 C25 C26 119.8(5) . . ? C25 C26 C27 120.5(4) . . ? C22 C27 C26 119.1(4) . . ? C4 N3 C2 110.0(3) . . ? C13 N12 C11 110.4(3) . . ? C1 S1 C4 88.65(18) . . ? C13 S2 C10 88.36(19) . . ? C4 O1 C1 125(2) . . ? C10 O2 C13 128(2) . . ? C10 O2 C11 46.1(11) . . ? C13 O2 C11 82.5(15) . . ? 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 C14 C1 C2 N3 -176.8(3) . . . . ? O1 C1 C2 N3 -4.1(8) . . . . ? S1 C1 C2 N3 1.3(4) . . . . ? C14 C1 C2 C5 0.7(6) . . . . ? O1 C1 C2 C5 173.4(8) . . . . ? S1 C1 C2 C5 178.8(3) . . . . ? C1 C2 C5 C9 42.4(6) . . . . ? N3 C2 C5 C9 -140.2(4) . . . . ? C1 C2 C5 C6 -136.6(4) . . . . ? N3 C2 C5 C6 40.8(5) . . . . ? C9 C5 C6 F2 -145.9(3) . . . . ? C2 C5 C6 F2 33.3(5) . . . . ? C9 C5 C6 F1 94.4(4) . . . . ? C2 C5 C6 F1 -86.5(4) . . . . ? C9 C5 C6 C7 -23.5(4) . . . . ? C2 C5 C6 C7 155.6(3) . . . . ? F2 C6 C7 F3 -84.2(4) . . . . ? F1 C6 C7 F3 31.2(5) . . . . ? C5 C6 C7 F3 151.1(3) . . . . ? F2 C6 C7 F4 35.4(4) . . . . ? F1 C6 C7 F4 150.8(3) . . . . ? C5 C6 C7 F4 -89.4(4) . . . . ? F2 C6 C7 C8 151.5(3) . . . . ? F1 C6 C7 C8 -93.1(4) . . . . ? C5 C6 C7 C8 26.8(4) . . . . ? F3 C7 C8 F6 90.4(4) . . . . ? F4 C7 C8 F6 -28.8(4) . . . . ? C6 C7 C8 F6 -144.5(3) . . . . ? F3 C7 C8 F5 -25.9(4) . . . . ? F4 C7 C8 F5 -145.1(3) . . . . ? C6 C7 C8 F5 99.2(3) . . . . ? F3 C7 C8 C9 -146.4(3) . . . . ? F4 C7 C8 C9 94.4(3) . . . . ? C6 C7 C8 C9 -21.3(4) . . . . ? C2 C5 C9 C11 13.9(6) . . . . ? C6 C5 C9 C11 -167.0(3) . . . . ? C2 C5 C9 C8 -169.2(3) . . . . ? C6 C5 C9 C8 9.9(4) . . . . ? F6 C8 C9 C5 128.5(3) . . . . ? F5 C8 C9 C5 -111.0(3) . . . . ? C7 C8 C9 C5 7.8(4) . . . . ? F6 C8 C9 C11 -54.4(5) . . . . ? F5 C8 C9 C11 66.1(4) . . . . ? C7 C8 C9 C11 -175.1(3) . . . . ? O2 C10 C11 N12 6.6(11) . . . . ? C15 C10 C11 N12 -179.0(3) . . . . ? S2 C10 C11 N12 -0.4(4) . . . . ? O2 C10 C11 C9 -172.4(11) . . . . ? C15 C10 C11 C9 1.9(6) . . . . ? S2 C10 C11 C9 -179.5(3) . . . . ? C15 C10 C11 O2 174.4(12) . . . . ? S2 C10 C11 O2 -7.0(10) . . . . ? C5 C9 C11 C10 44.8(6) . . . . ? C8 C9 C11 C10 -131.8(4) . . . . ? C5 C9 C11 N12 -134.2(4) . . . . ? C8 C9 C11 N12 49.2(5) . . . . ? C5 C9 C11 O2 23(3) . . . . ? C8 C9 C11 O2 -154(3) . . . . ? O1 C4 C16 C17 154.5(16) . . . . ? N3 C4 C16 C17 -15.6(5) . . . . ? S1 C4 C16 C17 164.1(3) . . . . ? O1 C4 C16 C21 -26.8(17) . . . . ? N3 C4 C16 C21 163.2(3) . . . . ? S1 C4 C16 C21 -17.1(5) . . . . ? C21 C16 C17 C18 1.9(5) . . . . ? C4 C16 C17 C18 -179.2(3) . . . . ? C16 C17 C18 C19 -0.9(5) . . . . ? C17 C18 C19 C20 -0.9(6) . . . . ? C18 C19 C20 C21 1.6(6) . . . . ? C17 C16 C21 C20 -1.2(5) . . . . ? C4 C16 C21 C20 180.0(3) . . . . ? C19 C20 C21 C16 -0.6(6) . . . . ? N12 C13 C22 C23 -6.7(5) . . . . ? O2 C13 C22 C23 -172.2(16) . . . . ? S2 C13 C22 C23 175.7(3) . . . . ? N12 C13 C22 C27 170.3(4) . . . . ? O2 C13 C22 C27 4.8(17) . . . . ? S2 C13 C22 C27 -7.2(5) . . . . ? C27 C22 C23 C24 0.7(6) . . . . ? C13 C22 C23 C24 177.9(3) . . . . ? C22 C23 C24 C25 -0.4(6) . . . . ? C23 C24 C25 C26 0.0(7) . . . . ? C24 C25 C26 C27 0.1(7) . . . . ? C23 C22 C27 C26 -0.6(5) . . . . ? C13 C22 C27 C26 -177.6(3) . . . . ? C25 C26 C27 C22 0.2(6) . . . . ? O1 C4 N3 C2 8.6(12) . . . . ? C16 C4 N3 C2 -179.1(3) . . . . ? S1 C4 N3 C2 1.2(4) . . . . ? C1 C2 N3 C4 -1.6(4) . . . . ? C5 C2 N3 C4 -179.2(3) . . . . ? O2 C13 N12 C11 -4.3(10) . . . . ? C22 C13 N12 C11 -175.2(3) . . . . ? S2 C13 N12 C11 2.4(4) . . . . ? C10 C11 N12 C13 -1.3(4) . . . . ? C9 C11 N12 C13 177.8(3) . . . . ? O2 C11 N12 C13 3.4(8) . . . . ? C2 C1 S1 C4 -0.5(3) . . . . ? C14 C1 S1 C4 177.9(3) . . . . ? O1 C1 S1 C4 12.2(18) . . . . ? O1 C4 S1 C1 -30(4) . . . . ? N3 C4 S1 C1 -0.5(3) . . . . ? C16 C4 S1 C1 179.8(3) . . . . ? N12 C13 S2 C10 -2.3(3) . . . . ? O2 C13 S2 C10 15(2) . . . . ? C22 C13 S2 C10 175.4(3) . . . . ? O2 C10 S2 C13 -20(3) . . . . ? C11 C10 S2 C13 1.4(3) . . . . ? C15 C10 S2 C13 -179.8(3) . . . . ? N3 C4 O1 C1 -13(2) . . . . ? C16 C4 O1 C1 174.7(9) . . . . ? S1 C4 O1 C1 139(6) . . . . ? C2 C1 O1 C4 12(2) . . . . ? C14 C1 O1 C4 -177.3(11) . . . . ? S1 C1 O1 C4 -156(4) . . . . ? C11 C10 O2 C13 -12(2) . . . . ? C15 C10 O2 C13 174.7(10) . . . . ? S2 C10 O2 C13 149(5) . . . . ? C15 C10 O2 C11 -173.7(13) . . . . ? S2 C10 O2 C11 160(3) . . . . ? N12 C13 O2 C10 11(2) . . . . ? C22 C13 O2 C10 179.4(10) . . . . ? S2 C13 O2 C10 -153(4) . . . . ? N12 C13 O2 C11 3.0(7) . . . . ? C22 C13 O2 C11 171.0(8) . . . . ? S2 C13 O2 C11 -161(3) . . . . ? N12 C11 O2 C10 -173.8(10) . . . . ? C9 C11 O2 C10 27(4) . . . . ? C10 C11 O2 C13 170.8(16) . . . . ? N12 C11 O2 C13 -2.9(7) . . . . ? C9 C11 O2 C13 -162(2) . . . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 0.688 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.072 #===END #===END data_1a _database_code_depnum_ccdc_archive 'CCDC 282862' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1,2-bis(5-methyl-2-phenyl-4-oxazolyl)perfluorocyclopentene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H16 F6 N2 O2' _chemical_formula_weight 490.40 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.618(3) _cell_length_b 17.791(5) _cell_length_c 10.274(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.773(5) _cell_angle_gamma 90.00 _cell_volume 2112.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 988 _cell_measurement_theta_min 2.290 _cell_measurement_theta_max 26.769 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.763866 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'sadabs sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0005 _diffrn_reflns_number 11879 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.11 _reflns_number_total 4256 _reflns_number_gt 3696 _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^)+(0.0479P)^2^+0.8675P] 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 calculated _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4256 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0939 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _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 F6 F 0.74367(7) 1.17718(5) 0.62205(8) 0.0263(2) Uani 1 1 d . . . F5 F 0.87512(7) 1.20794(4) 0.77850(8) 0.0265(2) Uani 1 1 d . . . O1 O 0.83368(8) 0.82220(5) 0.81431(9) 0.0196(2) Uani 1 1 d . . . F3 F 0.75200(9) 1.16661(5) 0.95663(9) 0.0379(2) Uani 1 1 d . . . F1 F 0.66765(9) 1.03488(5) 0.95923(9) 0.0364(2) Uani 1 1 d . . . F2 F 0.58085(8) 1.04432(5) 0.76286(10) 0.0373(2) Uani 1 1 d . . . O2 O 1.11477(8) 1.07301(5) 0.56989(9) 0.0205(2) Uani 1 1 d . . . F4 F 0.61009(8) 1.18581(5) 0.80579(11) 0.0404(3) Uani 1 1 d . . . N12 N 1.02929(10) 1.00412(6) 0.71367(11) 0.0187(2) Uani 1 1 d . . . C11 C 0.95887(11) 1.06575(7) 0.67432(12) 0.0176(3) Uani 1 1 d . . . C1 C 0.85761(12) 0.89391(7) 0.86074(13) 0.0200(3) Uani 1 1 d . . . C23 C 1.31026(12) 0.97753(8) 0.57575(13) 0.0210(3) Uani 1 1 d . . . N3 N 0.72784(10) 0.90141(6) 0.68356(11) 0.0186(2) Uani 1 1 d . . . C2 C 0.79467(12) 0.94186(7) 0.78028(13) 0.0183(3) Uani 1 1 d . . . C22 C 1.22180(11) 0.96370(8) 0.65549(12) 0.0184(3) Uani 1 1 d . . . C4 C 0.75453(11) 0.83181(8) 0.70800(12) 0.0178(3) Uani 1 1 d . . . C14 C 0.94085(14) 0.90114(9) 0.97880(15) 0.0270(3) Uani 1 1 d . . . C13 C 1.11935(12) 1.01142(7) 0.65022(12) 0.0180(3) Uani 1 1 d . . . C17 C 0.64030(12) 0.77699(8) 0.51761(13) 0.0217(3) Uani 1 1 d . . . C16 C 0.70737(11) 0.76558(8) 0.63646(13) 0.0191(3) Uani 1 1 d . . . C24 C 1.40597(12) 0.93068(8) 0.58412(14) 0.0238(3) Uani 1 1 d . . . C27 C 1.23106(12) 0.90347(8) 0.74348(14) 0.0224(3) Uani 1 1 d . . . C8 C 0.79684(12) 1.15393(8) 0.73913(13) 0.0196(3) Uani 1 1 d . . . C18 C 0.58812(13) 0.71627(9) 0.45066(14) 0.0249(3) Uani 1 1 d . . . C9 C 0.84986(11) 1.07703(7) 0.73042(12) 0.0177(3) Uani 1 1 d . . . C10 C 1.01163(12) 1.10769(8) 0.58633(13) 0.0201(3) Uani 1 1 d . . . C26 C 1.32740(13) 0.85762(8) 0.75121(14) 0.0238(3) Uani 1 1 d . . . C15 C 0.98717(15) 1.17638(9) 0.50587(16) 0.0273(3) Uani 1 1 d . . . C25 C 1.41510(12) 0.87088(8) 0.67132(14) 0.0233(3) Uani 1 1 d . . . C21 C 0.72332(13) 0.69278(8) 0.68633(14) 0.0240(3) Uani 1 1 d . . . C6 C 0.68129(12) 1.05959(8) 0.83701(14) 0.0238(3) Uani 1 1 d . . . C5 C 0.78415(12) 1.02465(8) 0.78248(12) 0.0187(3) Uani 1 1 d . . . C7 C 0.70532(13) 1.14478(8) 0.83704(14) 0.0241(3) Uani 1 1 d . . . C20 C 0.67053(14) 0.63237(8) 0.61807(15) 0.0277(3) Uani 1 1 d . . . C19 C 0.60256(13) 0.64402(9) 0.50053(15) 0.0267(3) Uani 1 1 d . . . H26 H 1.3363(14) 0.8158(10) 0.8120(17) 0.024(4) Uiso 1 1 d . . . H23 H 1.3028(14) 1.0176(10) 0.5148(17) 0.024(4) Uiso 1 1 d . . . H25 H 1.4827(15) 0.8379(10) 0.6757(17) 0.029(4) Uiso 1 1 d . . . H27 H 1.1675(15) 0.8944(10) 0.7962(17) 0.029(4) Uiso 1 1 d . . . H17 H 0.6307(14) 0.8282(10) 0.4835(16) 0.025(4) Uiso 1 1 d . . . H24 H 1.4667(16) 0.9385(10) 0.5305(17) 0.031(5) Uiso 1 1 d . . . H18 H 0.5419(14) 0.7255(9) 0.3701(17) 0.024(4) Uiso 1 1 d . . . H21 H 0.7693(15) 0.6850(10) 0.7690(18) 0.028(4) Uiso 1 1 d . . . H20 H 0.6826(15) 0.5827(11) 0.6534(18) 0.035(5) Uiso 1 1 d . . . H14A H 0.9347(17) 0.9500(12) 1.021(2) 0.046(6) Uiso 1 1 d . . . H14B H 1.0198(18) 0.8968(11) 0.9582(19) 0.039(5) Uiso 1 1 d . . . H15C H 0.910(2) 1.1932(12) 0.506(2) 0.050(6) Uiso 1 1 d . . . H14C H 0.9260(17) 0.8626(12) 1.045(2) 0.045(5) Uiso 1 1 d . . . H19 H 0.5631(14) 0.6027(10) 0.4540(17) 0.027(4) Uiso 1 1 d . . . H15A H 1.001(2) 1.1660(13) 0.415(2) 0.061(7) Uiso 1 1 d . . . H15B H 1.036(2) 1.2155(15) 0.535(2) 0.067(7) 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 F6 0.0313(5) 0.0234(4) 0.0234(4) 0.0051(3) -0.0003(3) 0.0061(4) F5 0.0280(5) 0.0170(4) 0.0344(5) -0.0050(3) 0.0033(3) -0.0044(3) O1 0.0212(5) 0.0162(5) 0.0208(5) 0.0002(4) -0.0012(4) -0.0004(4) F3 0.0601(7) 0.0297(5) 0.0259(5) -0.0084(4) 0.0143(4) -0.0095(4) F1 0.0535(6) 0.0241(5) 0.0357(5) 0.0050(4) 0.0253(4) 0.0030(4) F2 0.0196(5) 0.0338(5) 0.0582(6) -0.0100(5) 0.0034(4) -0.0013(4) O2 0.0210(5) 0.0191(5) 0.0214(5) 0.0038(4) 0.0030(4) 0.0011(4) F4 0.0320(5) 0.0266(5) 0.0661(7) 0.0135(5) 0.0215(5) 0.0117(4) N12 0.0197(6) 0.0170(6) 0.0193(5) -0.0002(4) 0.0011(4) 0.0013(4) C11 0.0195(6) 0.0147(6) 0.0179(6) -0.0012(5) -0.0011(5) 0.0004(5) C1 0.0217(7) 0.0161(7) 0.0225(7) -0.0012(5) 0.0029(5) -0.0022(5) C23 0.0238(7) 0.0197(7) 0.0194(6) 0.0027(5) 0.0015(5) -0.0007(5) N3 0.0211(6) 0.0172(6) 0.0176(5) -0.0003(4) 0.0025(4) -0.0005(4) C2 0.0193(6) 0.0168(6) 0.0191(6) -0.0003(5) 0.0029(5) -0.0015(5) C22 0.0199(7) 0.0181(7) 0.0170(6) -0.0021(5) 0.0003(5) -0.0001(5) C4 0.0184(6) 0.0185(7) 0.0167(6) 0.0007(5) 0.0027(5) 0.0006(5) C14 0.0294(8) 0.0230(8) 0.0269(8) 0.0005(6) -0.0059(6) -0.0023(6) C13 0.0215(7) 0.0158(6) 0.0161(6) 0.0002(5) -0.0009(5) -0.0013(5) C17 0.0241(7) 0.0208(7) 0.0208(7) -0.0015(5) 0.0044(5) 0.0012(6) C16 0.0190(6) 0.0184(7) 0.0206(6) -0.0024(5) 0.0052(5) 0.0006(5) C24 0.0214(7) 0.0265(8) 0.0241(7) 0.0020(6) 0.0058(5) 0.0002(6) C27 0.0235(7) 0.0231(7) 0.0214(7) 0.0030(5) 0.0055(5) 0.0013(6) C8 0.0212(7) 0.0162(6) 0.0209(6) 0.0001(5) 0.0002(5) -0.0012(5) C18 0.0240(7) 0.0288(8) 0.0216(7) -0.0051(6) 0.0012(6) 0.0005(6) C9 0.0198(6) 0.0166(6) 0.0159(6) -0.0009(5) -0.0021(5) 0.0004(5) C10 0.0194(7) 0.0188(7) 0.0215(6) 0.0000(5) 0.0000(5) 0.0011(5) C26 0.0273(7) 0.0216(7) 0.0227(7) 0.0054(6) 0.0035(5) 0.0039(6) C15 0.0281(8) 0.0230(8) 0.0310(8) 0.0099(6) 0.0041(6) 0.0026(6) C25 0.0209(7) 0.0251(7) 0.0239(7) 0.0012(6) 0.0024(5) 0.0047(6) C21 0.0265(7) 0.0201(7) 0.0252(7) -0.0002(6) 0.0007(6) 0.0020(6) C6 0.0238(7) 0.0213(7) 0.0270(7) 0.0011(6) 0.0061(6) -0.0007(6) C5 0.0201(7) 0.0178(7) 0.0176(6) -0.0011(5) -0.0006(5) 0.0001(5) C7 0.0261(7) 0.0204(7) 0.0267(7) -0.0007(6) 0.0071(6) 0.0039(6) C20 0.0315(8) 0.0180(7) 0.0339(8) -0.0013(6) 0.0041(6) 0.0001(6) C19 0.0258(8) 0.0234(8) 0.0314(8) -0.0092(6) 0.0049(6) -0.0031(6) _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 F6 C8 1.3602(16) . ? F5 C8 1.3566(16) . ? O1 C4 1.3660(16) . ? O1 C1 1.3806(16) . ? F3 C7 1.3492(18) . ? F1 C6 1.3546(17) . ? F2 C6 1.3553(18) . ? O2 C13 1.3696(16) . ? O2 C10 1.3733(17) . ? F4 C7 1.3375(17) . ? N12 C13 1.2938(18) . ? N12 C11 1.4030(17) . ? C11 C10 1.3642(19) . ? C11 C9 1.4571(19) . ? C1 C2 1.3506(19) . ? C1 C14 1.479(2) . ? C23 C24 1.385(2) . ? C23 C22 1.3991(19) . ? N3 C4 1.2948(18) . ? N3 C2 1.3975(17) . ? C2 C5 1.4783(19) . ? C22 C27 1.3991(19) . ? C22 C13 1.4586(19) . ? C4 C16 1.4655(19) . ? C17 C18 1.387(2) . ? C17 C16 1.3957(19) . ? C16 C21 1.398(2) . ? C24 C25 1.388(2) . ? C27 C26 1.381(2) . ? C8 C9 1.5067(19) . ? C8 C7 1.544(2) . ? C18 C19 1.388(2) . ? C9 C5 1.349(2) . ? C10 C15 1.487(2) . ? C26 C25 1.391(2) . ? C21 C20 1.392(2) . ? C6 C5 1.5044(19) . ? C6 C7 1.541(2) . ? C20 C19 1.390(2) . ? 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 C4 O1 C1 104.86(10) . . ? C13 O2 C10 105.48(10) . . ? C13 N12 C11 104.73(11) . . ? C10 C11 N12 109.29(12) . . ? C10 C11 C9 130.78(12) . . ? N12 C11 C9 119.90(12) . . ? C2 C1 O1 107.13(12) . . ? C2 C1 C14 135.74(13) . . ? O1 C1 C14 117.13(12) . . ? C24 C23 C22 119.35(13) . . ? C4 N3 C2 104.45(11) . . ? C1 C2 N3 109.74(12) . . ? C1 C2 C5 131.33(12) . . ? N3 C2 C5 118.89(11) . . ? C27 C22 C23 119.99(13) . . ? C27 C22 C13 118.63(12) . . ? C23 C22 C13 121.38(12) . . ? N3 C4 O1 113.80(12) . . ? N3 C4 C16 126.98(12) . . ? O1 C4 C16 119.21(12) . . ? N12 C13 O2 113.54(12) . . ? N12 C13 C22 128.41(12) . . ? O2 C13 C22 118.05(12) . . ? C18 C17 C16 119.89(13) . . ? C17 C16 C21 119.80(13) . . ? C17 C16 C4 118.00(12) . . ? C21 C16 C4 122.14(12) . . ? C23 C24 C25 120.67(13) . . ? C26 C27 C22 119.92(13) . . ? F5 C8 F6 106.23(10) . . ? F5 C8 C9 113.27(11) . . ? F6 C8 C9 112.07(11) . . ? F5 C8 C7 111.43(11) . . ? F6 C8 C7 109.08(11) . . ? C9 C8 C7 104.80(11) . . ? C17 C18 C19 120.52(14) . . ? C5 C9 C11 127.64(13) . . ? C5 C9 C8 110.65(12) . . ? C11 C9 C8 121.69(12) . . ? C11 C10 O2 106.95(11) . . ? C11 C10 C15 138.12(14) . . ? O2 C10 C15 114.92(12) . . ? C27 C26 C25 120.23(13) . . ? C24 C25 C26 119.85(13) . . ? C20 C21 C16 119.69(13) . . ? F1 C6 F2 106.36(12) . . ? F1 C6 C5 112.49(12) . . ? F2 C6 C5 112.28(12) . . ? F1 C6 C7 110.92(12) . . ? F2 C6 C7 110.05(12) . . ? C5 C6 C7 104.81(11) . . ? C9 C5 C2 129.15(13) . . ? C9 C5 C6 111.39(12) . . ? C2 C5 C6 119.16(12) . . ? F4 C7 F3 107.97(12) . . ? F4 C7 C6 113.03(12) . . ? F3 C7 C6 109.85(12) . . ? F4 C7 C8 113.17(12) . . ? F3 C7 C8 108.84(12) . . ? C6 C7 C8 103.90(11) . . ? C19 C20 C21 120.37(14) . . ? C18 C19 C20 119.72(14) . . ? 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 C13 N12 C11 C10 0.35(14) . . . . ? C13 N12 C11 C9 -178.05(12) . . . . ? C4 O1 C1 C2 -1.11(14) . . . . ? C4 O1 C1 C14 179.12(12) . . . . ? O1 C1 C2 N3 1.40(15) . . . . ? C14 C1 C2 N3 -178.89(16) . . . . ? O1 C1 C2 C5 179.15(13) . . . . ? C14 C1 C2 C5 -1.1(3) . . . . ? C4 N3 C2 C1 -1.11(15) . . . . ? C4 N3 C2 C5 -179.18(12) . . . . ? C24 C23 C22 C27 0.6(2) . . . . ? C24 C23 C22 C13 -179.99(13) . . . . ? C2 N3 C4 O1 0.40(15) . . . . ? C2 N3 C4 C16 179.00(12) . . . . ? C1 O1 C4 N3 0.43(15) . . . . ? C1 O1 C4 C16 -178.29(11) . . . . ? C11 N12 C13 O2 -0.57(14) . . . . ? C11 N12 C13 C22 178.74(13) . . . . ? C10 O2 C13 N12 0.57(14) . . . . ? C10 O2 C13 C22 -178.82(11) . . . . ? C27 C22 C13 N12 -3.4(2) . . . . ? C23 C22 C13 N12 177.16(13) . . . . ? C27 C22 C13 O2 175.84(12) . . . . ? C23 C22 C13 O2 -3.56(18) . . . . ? C18 C17 C16 C21 1.1(2) . . . . ? C18 C17 C16 C4 -176.05(12) . . . . ? N3 C4 C16 C17 10.8(2) . . . . ? O1 C4 C16 C17 -170.62(12) . . . . ? N3 C4 C16 C21 -166.27(14) . . . . ? O1 C4 C16 C21 12.26(19) . . . . ? C22 C23 C24 C25 -0.6(2) . . . . ? C23 C22 C27 C26 -0.2(2) . . . . ? C13 C22 C27 C26 -179.60(13) . . . . ? C16 C17 C18 C19 -0.4(2) . . . . ? C10 C11 C9 C5 156.92(14) . . . . ? N12 C11 C9 C5 -25.1(2) . . . . ? C10 C11 C9 C8 -24.4(2) . . . . ? N12 C11 C9 C8 153.59(12) . . . . ? F5 C8 C9 C5 136.26(12) . . . . ? F6 C8 C9 C5 -103.57(13) . . . . ? C7 C8 C9 C5 14.59(15) . . . . ? F5 C8 C9 C11 -42.61(17) . . . . ? F6 C8 C9 C11 77.56(15) . . . . ? C7 C8 C9 C11 -164.27(12) . . . . ? N12 C11 C10 O2 -0.02(14) . . . . ? C9 C11 C10 O2 178.15(13) . . . . ? N12 C11 C10 C15 178.43(17) . . . . ? C9 C11 C10 C15 -3.4(3) . . . . ? C13 O2 C10 C11 -0.31(14) . . . . ? C13 O2 C10 C15 -179.16(12) . . . . ? C22 C27 C26 C25 -0.3(2) . . . . ? C23 C24 C25 C26 0.1(2) . . . . ? C27 C26 C25 C24 0.4(2) . . . . ? C17 C16 C21 C20 -1.1(2) . . . . ? C4 C16 C21 C20 175.98(13) . . . . ? C11 C9 C5 C2 -9.7(2) . . . . ? C8 C9 C5 C2 171.56(13) . . . . ? C11 C9 C5 C6 176.75(12) . . . . ? C8 C9 C5 C6 -2.04(15) . . . . ? C1 C2 C5 C9 86.9(2) . . . . ? N3 C2 C5 C9 -95.49(17) . . . . ? C1 C2 C5 C6 -99.90(18) . . . . ? N3 C2 C5 C6 77.68(16) . . . . ? F1 C6 C5 C9 -132.02(13) . . . . ? F2 C6 C5 C9 108.05(13) . . . . ? C7 C6 C5 C9 -11.40(15) . . . . ? F1 C6 C5 C2 53.67(17) . . . . ? F2 C6 C5 C2 -66.27(16) . . . . ? C7 C6 C5 C2 174.28(12) . . . . ? F1 C6 C7 F4 -95.93(15) . . . . ? F2 C6 C7 F4 21.49(17) . . . . ? C5 C6 C7 F4 142.42(12) . . . . ? F1 C6 C7 F3 24.72(16) . . . . ? F2 C6 C7 F3 142.14(12) . . . . ? C5 C6 C7 F3 -96.93(13) . . . . ? F1 C6 C7 C8 141.01(12) . . . . ? F2 C6 C7 C8 -101.57(13) . . . . ? C5 C6 C7 C8 19.36(14) . . . . ? F5 C8 C7 F4 93.68(14) . . . . ? F6 C8 C7 F4 -23.29(16) . . . . ? C9 C8 C7 F4 -143.46(12) . . . . ? F5 C8 C7 F3 -26.35(15) . . . . ? F6 C8 C7 F3 -143.32(11) . . . . ? C9 C8 C7 F3 96.51(12) . . . . ? F5 C8 C7 C6 -143.35(11) . . . . ? F6 C8 C7 C6 99.68(12) . . . . ? C9 C8 C7 C6 -20.49(14) . . . . ? C16 C21 C20 C19 0.3(2) . . . . ? C17 C18 C19 C20 -0.5(2) . . . . ? C21 C20 C19 C18 0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 27.12 _diffrn_measured_fraction_theta_full 0.913 _refine_diff_density_max 0.309 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.053