Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (c) The Royal Society of Chemistry 2004 data_global # Submission details _publ_requested_journal 'Journal of Materials Chemistry' _publ_requested_category 'full paper' _publ_contact_author_name 'Prof. Jean-Marc Fabre' _publ_contact_author_address ; Laboratoire de Chimie Organique, Heterochimie et Materiaux Organiques, UMR 5076, ENSCM, 8 rue de l'Ecole Normale, F 34296 Montpellier cedex-5, FRANCE ; _publ_contact_author_email 'jmfabre@cit.enscm.fr ' _publ_contact_author_phone '+33 (0)4 67 14 43 60 ' _publ_contact_author_fax '+33 (0)4 67 14 43 19 ' _publ_section_title ; Structural study and electrical conductivity of salts based on functionalised TTF containing peripheral selenium atoms ; loop_ _publ_author_name _publ_author_address 'Lakhemici Kaboub' ; Laboratoire de Chimie des Materiaux Organiques, Centre universitaire de Tebessa, Route de Constantine, 12000 Tebessa, ALGERIE ; 'Jean-Pierre Legros' ; Laboratoire de Chimie de Coordination du CNRS, CNRS-UPR 8241, 205 route de Narbonne, F 31077 Toulouse cedex-4, FRANCE ; 'Bruno Donnadieu' ; Laboratoire de Chimie de Coordination du CNRS, CNRS-UPR 8241, 205 route de Narbonne, F 31077 Toulouse cedex-4, FRANCE ; 'Abdel-Krim Gouasmia' ; Laboratoire de Chimie des Materiaux Organiques, Centre universitaire de Tebessa, Route de Constantine, 12000 Tebessa ALGERIE ; 'Louiza Boudiba' ; Laboratoire de Chimie des Materiaux Organiques, Centre universitaire de Tebessa, Route de Constantine, 12000 Tebessa ALGERIE ; 'Jean-Marc Fabre' ; Laboratoire de Chimie Organique, Heterochimie et Materiaux Organiques, UMR 5076, ENSCM, 8 rue de l'Ecole Normale, F 34296 Montpellier cedex-5, FRANCE ; #=== data_AcOPM-BTTF _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-acetoxyphenyl)-5-methyl-4',5'benzotetrathiafulvalene ; _chemical_name_common AcOPM-BTTF _chemical_melting_point 161 _chemical_formula_moiety 'C19 H14 O2 S4' _chemical_formula_sum 'C19 H14 O2 S4' _chemical_formula_weight 402.54 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' 'O' 'O' 0.0106 0.0060 '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 'P 1 21/c 1' 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 15.013(1) _cell_length_b 9.462(1) _cell_length_c 13.355(1) _cell_angle_alpha 90.00 _cell_angle_beta 109.64(1) _cell_angle_gamma 90.00 _cell_volume 1786.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 28.0 _exptl_crystal_id 'Ie' _exptl_crystal_description 'plate' _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.70 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.542 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.6711 _exptl_absorpt_correction_T_max 0.8330 _exptl_absorpt_process_details ; Xabs2 - Parkin S., Moezzi B., Hope H., J. Appl. Cryst. 1995, 28, 53-56 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id X _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur Oxford Instrument CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30356 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4272 _reflns_number_gt 3855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis Oxford Instruments' _computing_cell_refinement 'CrysAlis Oxford Instruments' _computing_data_reduction 'CrysAlis Oxford Instruments' _computing_structure_solution ; SHELXS-97 (Sheldrick, 1997) SIR92 - A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi J. Appl. Cryst., 1993, 26, 343-350 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3 for Windows - L. J. Farrugia J. Appl. Cryst., 1997, 30, 565 ; _computing_publication_material ; WINGX - L. J. Farrugia J. Appl. Cryst., 1999, 32, 837-838 ; _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^)+(0.0668P)^2^+2.5879P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4272 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1332 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 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 S1 S 0.31290(4) 0.07054(6) 0.41167(5) 0.02755(16) Uani 1 1 d . . . S2 S 0.40900(4) 0.31845(6) 0.53857(5) 0.02761(16) Uani 1 1 d . . . S3 S 0.48335(4) 0.03046(6) 0.32082(4) 0.02341(15) Uani 1 1 d . . . S4 S 0.58171(4) 0.27824(6) 0.44266(5) 0.02372(15) Uani 1 1 d . . . O1 O 0.98791(11) 0.40982(19) 0.36667(14) 0.0282(4) Uani 1 1 d . . . O2 O 1.01155(16) 0.2556(3) 0.2494(2) 0.0565(7) Uani 1 1 d . . . C1 C 0.25523(16) 0.1520(2) 0.49048(17) 0.0230(4) Uani 1 1 d . . . C2 C 0.29983(15) 0.2692(2) 0.54989(17) 0.0218(4) Uani 1 1 d . . . C3 C 0.41115(15) 0.1839(2) 0.44873(17) 0.0213(4) Uani 1 1 d . . . C4 C 0.48297(15) 0.1665(2) 0.41073(17) 0.0206(4) Uani 1 1 d . . . C5 C 0.59144(14) 0.0774(2) 0.30663(17) 0.0205(4) Uani 1 1 d . . . C6 C 0.63630(14) 0.1902(2) 0.36198(16) 0.0197(4) Uani 1 1 d . . . C7 C 0.72817(14) 0.2470(2) 0.36229(17) 0.0188(4) Uani 1 1 d . . . C8 C 0.74350(16) 0.2743(3) 0.26694(17) 0.0248(4) Uani 1 1 d . . . H8 H 0.6941 0.2576 0.2015 0.030 Uiso 1 1 calc R . . C9 C 0.83010(16) 0.3258(3) 0.26596(18) 0.0256(5) Uani 1 1 d . . . H9 H 0.8400 0.3445 0.2006 0.031 Uiso 1 1 calc R . . C10 C 0.90160(15) 0.3491(2) 0.36205(18) 0.0225(4) Uani 1 1 d . . . C11 C 0.88759(16) 0.3268(3) 0.45807(18) 0.0260(5) Uani 1 1 d . . . H11 H 0.9368 0.3455 0.5233 0.031 Uiso 1 1 calc R . . C12 C 0.80055(15) 0.2765(2) 0.45779(18) 0.0235(4) Uani 1 1 d . . . H12 H 0.7901 0.2620 0.5234 0.028 Uiso 1 1 calc R . . C13 C 1.03716(17) 0.3559(3) 0.3061(2) 0.0309(5) Uani 1 1 d . . . C14 C 1.12526(18) 0.4392(3) 0.3225(2) 0.0345(6) Uani 1 1 d . . . H14A H 1.1289 0.5158 0.3731 0.041 Uiso 1 1 calc R . . H14B H 1.1244 0.4792 0.2545 0.041 Uiso 1 1 calc R . . H14C H 1.1804 0.3773 0.3507 0.041 Uiso 1 1 calc R . . C15 C 0.62589(17) -0.0170(3) 0.23699(19) 0.0268(5) Uani 1 1 d . . . H15A H 0.5789 -0.0910 0.2064 0.032 Uiso 1 1 calc R . . H15B H 0.6859 -0.0606 0.2795 0.032 Uiso 1 1 calc R . . H15C H 0.6354 0.0389 0.1796 0.032 Uiso 1 1 calc R . . C16 C 0.25754(18) 0.3411(3) 0.61389(19) 0.0278(5) Uani 1 1 d . . . H16 H 0.2872 0.4217 0.6537 0.033 Uiso 1 1 calc R . . C17 C 0.17173(19) 0.2928(3) 0.6183(2) 0.0337(5) Uani 1 1 d . . . H17 H 0.1428 0.3401 0.6621 0.040 Uiso 1 1 calc R . . C18 C 0.12767(18) 0.1762(3) 0.5594(2) 0.0355(6) Uani 1 1 d . . . H18 H 0.0687 0.1448 0.5631 0.043 Uiso 1 1 calc R . . C19 C 0.16851(17) 0.1046(3) 0.4951(2) 0.0288(5) Uani 1 1 d . . . H19 H 0.1380 0.0248 0.4549 0.035 Uiso 1 1 calc R . . 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 S1 0.0295(3) 0.0279(3) 0.0287(3) -0.0109(2) 0.0144(2) -0.0085(2) S2 0.0292(3) 0.0254(3) 0.0318(3) -0.0109(2) 0.0150(2) -0.0068(2) S3 0.0220(3) 0.0240(3) 0.0241(3) -0.0075(2) 0.0076(2) -0.0036(2) S4 0.0225(3) 0.0221(3) 0.0270(3) -0.0080(2) 0.0088(2) -0.0023(2) O1 0.0221(8) 0.0321(9) 0.0324(9) -0.0082(7) 0.0117(7) -0.0060(7) O2 0.0411(11) 0.0659(15) 0.0752(16) -0.0436(13) 0.0363(12) -0.0234(11) C1 0.0238(10) 0.0243(10) 0.0211(10) 0.0030(8) 0.0079(8) 0.0032(8) C2 0.0235(10) 0.0210(10) 0.0212(10) 0.0028(8) 0.0081(8) 0.0030(8) C3 0.0233(10) 0.0214(10) 0.0194(10) -0.0013(8) 0.0076(8) 0.0006(8) C4 0.0209(9) 0.0214(10) 0.0181(10) -0.0002(8) 0.0049(8) 0.0005(8) C5 0.0182(9) 0.0240(10) 0.0177(10) 0.0009(8) 0.0037(7) 0.0031(8) C6 0.0175(9) 0.0214(10) 0.0190(10) 0.0003(8) 0.0046(7) 0.0040(8) C7 0.0176(9) 0.0176(9) 0.0190(10) 0.0007(7) 0.0030(7) 0.0019(7) C8 0.0215(10) 0.0329(12) 0.0164(10) 0.0002(8) 0.0017(8) 0.0013(9) C9 0.0242(10) 0.0320(12) 0.0197(10) 0.0026(9) 0.0063(8) -0.0009(9) C10 0.0185(9) 0.0226(10) 0.0255(11) -0.0022(8) 0.0063(8) 0.0006(8) C11 0.0220(10) 0.0310(12) 0.0209(10) -0.0046(9) 0.0019(8) -0.0017(9) C12 0.0226(10) 0.0271(11) 0.0191(10) -0.0002(8) 0.0046(8) 0.0001(8) C13 0.0256(11) 0.0382(13) 0.0309(12) -0.0070(10) 0.0120(9) -0.0048(10) C14 0.0256(11) 0.0427(14) 0.0370(14) -0.0048(11) 0.0132(10) -0.0094(10) C15 0.0255(11) 0.0304(12) 0.0228(11) -0.0081(9) 0.0057(9) 0.0021(9) C16 0.0321(12) 0.0260(11) 0.0258(11) 0.0007(9) 0.0105(9) 0.0068(9) C17 0.0353(13) 0.0353(13) 0.0364(14) 0.0028(10) 0.0200(11) 0.0113(11) C18 0.0270(12) 0.0381(14) 0.0458(15) 0.0039(12) 0.0179(11) 0.0028(10) C19 0.0274(11) 0.0258(11) 0.0327(12) 0.0002(9) 0.0094(9) -0.0011(9) _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 S1 C1 1.750(2) . ? S1 C3 1.755(2) . ? S2 C3 1.757(2) . ? S2 C2 1.759(2) . ? S3 C5 1.753(2) . ? S3 C4 1.761(2) . ? S4 C4 1.753(2) . ? S4 C6 1.766(2) . ? O1 C13 1.366(3) . ? O1 C10 1.399(3) . ? O2 C13 1.193(3) . ? C1 C2 1.396(3) . ? C1 C19 1.397(3) . ? C2 C16 1.401(3) . ? C3 C4 1.347(3) . ? C5 C6 1.343(3) . ? C5 C15 1.501(3) . ? C6 C7 1.479(3) . ? C7 C8 1.392(3) . ? C7 C12 1.398(3) . ? C8 C9 1.392(3) . ? C9 C10 1.386(3) . ? C10 C11 1.384(3) . ? C11 C12 1.389(3) . ? C13 C14 1.491(3) . ? C16 C17 1.387(4) . ? C17 C18 1.387(4) . ? C18 C19 1.388(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 C1 S1 C3 95.75(11) . . ? C3 S2 C2 95.65(10) . . ? C5 S3 C4 95.97(10) . . ? C4 S4 C6 95.45(10) . . ? C13 O1 C10 119.90(19) . . ? C2 C1 C19 120.3(2) . . ? C2 C1 S1 116.85(17) . . ? C19 C1 S1 122.83(19) . . ? C1 C2 C16 120.2(2) . . ? C1 C2 S2 116.37(16) . . ? C16 C2 S2 123.38(18) . . ? C4 C3 S1 121.46(17) . . ? C4 C3 S2 123.16(18) . . ? S1 C3 S2 115.38(12) . . ? C3 C4 S4 123.56(18) . . ? C3 C4 S3 122.20(17) . . ? S4 C4 S3 114.22(12) . . ? C6 C5 C15 126.9(2) . . ? C6 C5 S3 116.92(16) . . ? C15 C5 S3 116.13(16) . . ? C5 C6 C7 125.79(19) . . ? C5 C6 S4 117.44(16) . . ? C7 C6 S4 116.76(15) . . ? C8 C7 C12 118.7(2) . . ? C8 C7 C6 120.37(19) . . ? C12 C7 C6 120.88(19) . . ? C7 C8 C9 121.0(2) . . ? C10 C9 C8 118.8(2) . . ? C11 C10 C9 121.5(2) . . ? C11 C10 O1 116.7(2) . . ? C9 C10 O1 121.6(2) . . ? C10 C11 C12 119.1(2) . . ? C11 C12 C7 120.8(2) . . ? O2 C13 O1 123.3(2) . . ? O2 C13 C14 126.5(2) . . ? O1 C13 C14 110.2(2) . . ? C17 C16 C2 118.9(2) . . ? C16 C17 C18 120.7(2) . . ? C17 C18 C19 120.9(2) . . ? C18 C19 C1 118.9(2) . . ? 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 C3 S1 C1 C2 0.82(19) . . . . ? C3 S1 C1 C19 -179.4(2) . . . . ? C19 C1 C2 C16 -0.6(3) . . . . ? S1 C1 C2 C16 179.20(17) . . . . ? C19 C1 C2 S2 179.60(18) . . . . ? S1 C1 C2 S2 -0.6(2) . . . . ? C3 S2 C2 C1 0.06(19) . . . . ? C3 S2 C2 C16 -179.7(2) . . . . ? C1 S1 C3 C4 178.7(2) . . . . ? C1 S1 C3 S2 -0.76(15) . . . . ? C2 S2 C3 C4 -178.9(2) . . . . ? C2 S2 C3 S1 0.50(14) . . . . ? S1 C3 C4 S4 178.66(12) . . . . ? S2 C3 C4 S4 -1.9(3) . . . . ? S1 C3 C4 S3 0.5(3) . . . . ? S2 C3 C4 S3 179.92(12) . . . . ? C6 S4 C4 C3 -178.4(2) . . . . ? C6 S4 C4 S3 -0.16(14) . . . . ? C5 S3 C4 C3 178.5(2) . . . . ? C5 S3 C4 S4 0.18(14) . . . . ? C4 S3 C5 C6 -0.13(19) . . . . ? C4 S3 C5 C15 177.42(17) . . . . ? C15 C5 C6 C7 2.2(4) . . . . ? S3 C5 C6 C7 179.49(16) . . . . ? C15 C5 C6 S4 -177.21(18) . . . . ? S3 C5 C6 S4 0.0(2) . . . . ? C4 S4 C6 C5 0.07(19) . . . . ? C4 S4 C6 C7 -179.43(16) . . . . ? C5 C6 C7 C8 50.5(3) . . . . ? S4 C6 C7 C8 -130.1(2) . . . . ? C5 C6 C7 C12 -130.6(2) . . . . ? S4 C6 C7 C12 48.9(3) . . . . ? C12 C7 C8 C9 2.0(3) . . . . ? C6 C7 C8 C9 -179.0(2) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? C8 C9 C10 C11 -2.1(4) . . . . ? C8 C9 C10 O1 -175.5(2) . . . . ? C13 O1 C10 C11 135.2(2) . . . . ? C13 O1 C10 C9 -51.1(3) . . . . ? C9 C10 C11 C12 1.6(4) . . . . ? O1 C10 C11 C12 175.3(2) . . . . ? C10 C11 C12 C7 0.8(4) . . . . ? C8 C7 C12 C11 -2.5(3) . . . . ? C6 C7 C12 C11 178.5(2) . . . . ? C10 O1 C13 O2 -1.6(4) . . . . ? C10 O1 C13 C14 178.8(2) . . . . ? C1 C2 C16 C17 0.9(3) . . . . ? S2 C2 C16 C17 -179.30(19) . . . . ? C2 C16 C17 C18 -0.8(4) . . . . ? C16 C17 C18 C19 0.3(4) . . . . ? C17 C18 C19 C1 0.0(4) . . . . ? C2 C1 C19 C18 0.1(4) . . . . ? S1 C1 C19 C18 -179.67(19) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.655 _refine_diff_density_min -0.711 _refine_diff_density_rms 0.091 #===END data_AcOPM-PDSTTF _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-acetoxyphenyl)-5-methyl-4',5'propylenediselenotetrathiafulvalene ; _chemical_name_common AcOPM-PDSTTF _chemical_melting_point 193 _chemical_formula_moiety 'C18 H16 O2 S4 Se2' _chemical_formula_sum 'C18 H16 O2 S4 Se2' _chemical_formula_weight 550.47 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' 'O' 'O' 0.0106 0.0060 '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' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' 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 6.641(2) _cell_length_b 23.033(5) _cell_length_c 13.830(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.19(2) _cell_angle_gamma 90.00 _cell_volume 2075.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 14 _exptl_crystal_id 'Id' _exptl_crystal_description 'block' _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 3.976 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.8458 _exptl_absorpt_correction_T_max 0.9990 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength_id 'X' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method 'omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 3.8 _diffrn_reflns_number 4428 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0682 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.97 _reflns_number_total 4071 _reflns_number_gt 2102 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4-Express' _computing_cell_refinement 'CAD4-Express' _computing_data_reduction ; WINGX - L. J. Farrugia J. Appl. Cryst., 1999, 32, 837-838 ; _computing_structure_solution ; SHELXS-97 (Sheldrick, 1997) SIR92 - A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi J. Appl. Cryst., 1993, 26, 343-350 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3 for Windows - L. J. Farrugia J. Appl. Cryst., 1997, 30, 565 ; _computing_publication_material ; WINGX - L. J. Farrugia J. Appl. Cryst., 1999, 32, 837-838 ; _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^)+(0.0796P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4071 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1229 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_restrained_S_all 0.964 _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 Se1 Se 0.20303(8) 0.22228(2) 0.38032(4) 0.05466(19) Uani 1 1 d . . . Se2 Se 0.66405(9) 0.28619(2) 0.33389(5) 0.0649(2) Uani 1 1 d . . . S1 S 0.2879(2) 0.12804(5) 0.23343(10) 0.0487(3) Uani 1 1 d . . . S2 S 0.6683(2) 0.18018(7) 0.19519(10) 0.0535(4) Uani 1 1 d . . . S3 S 0.2297(2) 0.05830(6) 0.02376(10) 0.0522(4) Uani 1 1 d . . . S4 S 0.6178(2) 0.10642(6) -0.00921(10) 0.0501(3) Uani 1 1 d . . . O1 O 0.7243(8) 0.0724(2) -0.4735(3) 0.0849(14) Uani 1 1 d . . . O2 O 1.0475(10) 0.0882(4) -0.4185(5) 0.168(3) Uani 1 1 d . . . C1 C 0.3681(7) 0.1936(2) 0.2938(3) 0.0434(11) Uani 1 1 d . . . C2 C 0.5393(8) 0.21710(19) 0.2753(4) 0.0447(12) Uani 1 1 d . . . C3 C 0.4632(8) 0.1320(2) 0.1530(4) 0.0462(12) Uani 1 1 d . . . C4 C 0.4405(8) 0.1034(2) 0.0676(3) 0.0415(11) Uani 1 1 d . . . C5 C 0.2785(8) 0.0521(2) -0.0957(3) 0.0441(12) Uani 1 1 d . . . C6 C 0.4557(7) 0.0737(2) -0.1115(3) 0.0395(11) Uani 1 1 d . . . C7 C 0.5365(7) 0.0728(2) -0.2035(3) 0.0422(11) Uani 1 1 d . . . C8 C 0.5165(8) 0.0235(2) -0.2630(4) 0.0464(12) Uani 1 1 d . . . H8 H 0.4551 -0.0096 -0.2435 0.056 Uiso 1 1 calc R . . C9 C 0.5870(9) 0.0234(2) -0.3503(4) 0.0557(14) Uani 1 1 d . . . H9 H 0.5733 -0.0096 -0.3898 0.067 Uiso 1 1 calc R . . C10 C 0.6781(9) 0.0727(3) -0.3784(4) 0.0552(14) Uani 1 1 d . . . C11 C 0.7079(9) 0.1210(2) -0.3202(4) 0.0558(14) Uani 1 1 d . . . H11 H 0.7761 0.1532 -0.3384 0.067 Uiso 1 1 calc R . . C12 C 0.6335(8) 0.1207(2) -0.2328(4) 0.0507(13) Uani 1 1 d . . . H12 H 0.6498 0.1536 -0.1931 0.061 Uiso 1 1 calc R . . C13 C 0.9102(13) 0.0789(3) -0.4873(6) 0.080(2) Uani 1 1 d . . . C14 C 0.9379(13) 0.0743(3) -0.5892(5) 0.085(2) Uani 1 1 d . . . H14A H 0.8080 0.0666 -0.6314 0.102 Uiso 1 1 calc R . . H14B H 1.0316 0.0432 -0.5946 0.102 Uiso 1 1 calc R . . H14C H 0.9924 0.1101 -0.6087 0.102 Uiso 1 1 calc R . . C15 C 0.1136(8) 0.0228(3) -0.1699(4) 0.0560(14) Uani 1 1 d . . . H15A H 0.0034 0.0113 -0.1383 0.067 Uiso 1 1 calc R . . H15B H 0.1699 -0.0108 -0.1960 0.067 Uiso 1 1 calc R . . H15C H 0.0625 0.0494 -0.2224 0.067 Uiso 1 1 calc R . . C16 C 0.7297(9) 0.2595(3) 0.4700(5) 0.0711(18) Uani 1 1 d . . . H16A H 0.7755 0.2194 0.4699 0.085 Uiso 1 1 calc R . . H16B H 0.8444 0.2822 0.5044 0.085 Uiso 1 1 calc R . . C17 C 0.3985(10) 0.2159(3) 0.5063(4) 0.0700(17) Uani 1 1 d . . . H17A H 0.3210 0.2156 0.5589 0.084 Uiso 1 1 calc R . . H17B H 0.4680 0.1787 0.5076 0.084 Uiso 1 1 calc R . . C18 C 0.5589(11) 0.2626(3) 0.5284(5) 0.0774(19) Uani 1 1 d . . . H18A H 0.6199 0.2608 0.5980 0.093 Uiso 1 1 calc R . . H18B H 0.4914 0.3000 0.5161 0.093 Uiso 1 1 calc R . . 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 Se1 0.0459(3) 0.0515(3) 0.0691(4) -0.0069(3) 0.0176(3) 0.0054(2) Se2 0.0514(3) 0.0506(3) 0.0915(5) -0.0095(3) 0.0106(3) -0.0095(3) S1 0.0600(9) 0.0482(7) 0.0417(8) -0.0037(5) 0.0189(6) -0.0124(6) S2 0.0478(8) 0.0669(9) 0.0475(8) -0.0048(6) 0.0139(6) -0.0079(7) S3 0.0542(8) 0.0597(8) 0.0460(8) -0.0041(6) 0.0174(7) -0.0121(6) S4 0.0461(7) 0.0615(8) 0.0454(8) -0.0102(6) 0.0155(6) -0.0077(6) O1 0.096(4) 0.108(4) 0.059(3) -0.019(2) 0.036(3) -0.033(3) O2 0.087(4) 0.336(11) 0.090(5) -0.012(6) 0.037(4) -0.020(6) C1 0.043(3) 0.045(3) 0.042(3) 0.000(2) 0.005(2) 0.002(2) C2 0.039(3) 0.037(3) 0.055(3) 0.004(2) 0.002(2) -0.002(2) C3 0.049(3) 0.053(3) 0.037(3) 0.005(2) 0.011(2) -0.004(2) C4 0.049(3) 0.041(3) 0.036(3) 0.003(2) 0.013(2) 0.003(2) C5 0.049(3) 0.046(3) 0.038(3) -0.001(2) 0.012(2) 0.001(2) C6 0.042(3) 0.044(3) 0.032(3) -0.001(2) 0.006(2) 0.002(2) C7 0.040(3) 0.049(3) 0.037(3) -0.001(2) 0.006(2) 0.002(2) C8 0.045(3) 0.051(3) 0.045(3) -0.003(2) 0.012(2) -0.004(2) C9 0.065(4) 0.061(3) 0.046(3) -0.012(3) 0.022(3) -0.006(3) C10 0.060(3) 0.071(4) 0.039(3) -0.001(3) 0.020(3) 0.001(3) C11 0.068(4) 0.055(3) 0.049(3) 0.000(3) 0.020(3) -0.013(3) C12 0.060(3) 0.053(3) 0.042(3) -0.008(2) 0.018(3) -0.006(3) C13 0.090(6) 0.086(5) 0.070(5) -0.007(4) 0.031(4) -0.012(4) C14 0.129(6) 0.075(4) 0.066(4) -0.006(3) 0.058(4) -0.019(4) C15 0.040(3) 0.077(4) 0.050(3) -0.004(3) 0.006(3) -0.010(3) C16 0.056(4) 0.068(4) 0.083(5) -0.033(3) -0.003(3) 0.001(3) C17 0.087(5) 0.074(4) 0.051(4) -0.021(3) 0.016(3) 0.004(3) C18 0.073(4) 0.086(5) 0.072(4) -0.034(4) 0.009(4) 0.005(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 Se1 C1 1.891(5) . ? Se1 C17 1.965(6) . ? Se2 C2 1.902(5) . ? Se2 C16 1.947(7) . ? S1 C1 1.758(5) . ? S1 C3 1.761(5) . ? S2 C2 1.746(5) . ? S2 C3 1.767(5) . ? S3 C5 1.750(5) . ? S3 C4 1.756(5) . ? S4 C4 1.734(5) . ? S4 C6 1.773(5) . ? O1 C13 1.295(8) . ? O1 C10 1.407(6) . ? O2 C13 1.203(9) . ? C1 C2 1.329(7) . ? C3 C4 1.336(7) . ? C5 C6 1.335(7) . ? C5 C15 1.508(7) . ? C6 C7 1.474(6) . ? C7 C12 1.378(7) . ? C7 C8 1.393(7) . ? C8 C9 1.377(7) . ? C9 C10 1.379(7) . ? C10 C11 1.366(7) . ? C11 C12 1.392(7) . ? C13 C14 1.460(8) . ? C16 C18 1.516(9) . ? C17 C18 1.505(9) . ? 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 C1 Se1 C17 99.8(2) . . ? C2 Se2 C16 98.3(2) . . ? C1 S1 C3 94.4(2) . . ? C2 S2 C3 94.2(2) . . ? C5 S3 C4 95.3(2) . . ? C4 S4 C6 95.3(2) . . ? C13 O1 C10 121.7(6) . . ? C2 C1 S1 116.9(4) . . ? C2 C1 Se1 127.0(4) . . ? S1 C1 Se1 116.1(3) . . ? C1 C2 S2 117.8(4) . . ? C1 C2 Se2 125.4(4) . . ? S2 C2 Se2 116.8(3) . . ? C4 C3 S1 123.8(4) . . ? C4 C3 S2 123.3(4) . . ? S1 C3 S2 112.8(3) . . ? C3 C4 S4 123.2(4) . . ? C3 C4 S3 123.0(4) . . ? S4 C4 S3 113.8(3) . . ? C6 C5 C15 127.1(4) . . ? C6 C5 S3 117.1(4) . . ? C15 C5 S3 115.8(4) . . ? C5 C6 C7 128.1(5) . . ? C5 C6 S4 116.5(4) . . ? C7 C6 S4 115.3(3) . . ? C12 C7 C8 118.4(4) . . ? C12 C7 C6 120.9(4) . . ? C8 C7 C6 120.7(4) . . ? C9 C8 C7 120.6(5) . . ? C8 C9 C10 119.3(5) . . ? C11 C10 C9 121.8(5) . . ? C11 C10 O1 121.4(5) . . ? C9 C10 O1 116.7(5) . . ? C10 C11 C12 118.1(5) . . ? C7 C12 C11 121.7(5) . . ? O2 C13 O1 120.2(7) . . ? O2 C13 C14 124.0(8) . . ? O1 C13 C14 115.9(7) . . ? C18 C16 Se2 116.7(5) . . ? C18 C17 Se1 116.6(5) . . ? C17 C18 C16 115.6(5) . . ? 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 C3 S1 C1 C2 -11.0(4) . . . . ? C3 S1 C1 Se1 170.1(3) . . . . ? C17 Se1 C1 C2 -64.0(5) . . . . ? C17 Se1 C1 S1 114.7(3) . . . . ? S1 C1 C2 S2 -1.0(6) . . . . ? Se1 C1 C2 S2 177.7(3) . . . . ? S1 C1 C2 Se2 -177.9(3) . . . . ? Se1 C1 C2 Se2 0.8(7) . . . . ? C3 S2 C2 C1 12.4(4) . . . . ? C3 S2 C2 Se2 -170.5(3) . . . . ? C16 Se2 C2 C1 63.6(5) . . . . ? C16 Se2 C2 S2 -113.3(3) . . . . ? C1 S1 C3 C4 -159.0(5) . . . . ? C1 S1 C3 S2 18.8(3) . . . . ? C2 S2 C3 C4 158.7(5) . . . . ? C2 S2 C3 S1 -19.2(3) . . . . ? S1 C3 C4 S4 -178.4(3) . . . . ? S2 C3 C4 S4 4.0(7) . . . . ? S1 C3 C4 S3 0.7(7) . . . . ? S2 C3 C4 S3 -176.9(3) . . . . ? C6 S4 C4 C3 -167.4(4) . . . . ? C6 S4 C4 S3 13.4(3) . . . . ? C5 S3 C4 C3 167.2(4) . . . . ? C5 S3 C4 S4 -13.7(3) . . . . ? C4 S3 C5 C6 8.6(4) . . . . ? C4 S3 C5 C15 -171.3(4) . . . . ? C15 C5 C6 C7 -2.0(9) . . . . ? S3 C5 C6 C7 178.2(4) . . . . ? C15 C5 C6 S4 179.3(4) . . . . ? S3 C5 C6 S4 -0.5(5) . . . . ? C4 S4 C6 C5 -8.0(4) . . . . ? C4 S4 C6 C7 173.2(4) . . . . ? C5 C6 C7 C12 138.9(6) . . . . ? S4 C6 C7 C12 -42.4(6) . . . . ? C5 C6 C7 C8 -41.2(8) . . . . ? S4 C6 C7 C8 137.6(4) . . . . ? C12 C7 C8 C9 -1.9(8) . . . . ? C6 C7 C8 C9 178.2(5) . . . . ? C7 C8 C9 C10 0.1(8) . . . . ? C8 C9 C10 C11 2.7(9) . . . . ? C8 C9 C10 O1 -172.5(5) . . . . ? C13 O1 C10 C11 64.2(9) . . . . ? C13 O1 C10 C9 -120.6(7) . . . . ? C9 C10 C11 C12 -3.5(9) . . . . ? O1 C10 C11 C12 171.5(5) . . . . ? C8 C7 C12 C11 1.1(8) . . . . ? C6 C7 C12 C11 -179.0(5) . . . . ? C10 C11 C12 C7 1.5(8) . . . . ? C10 O1 C13 O2 -3.5(12) . . . . ? C10 O1 C13 C14 176.4(5) . . . . ? C2 Se2 C16 C18 -82.9(5) . . . . ? C1 Se1 C17 C18 78.7(5) . . . . ? Se1 C17 C18 C16 -73.5(7) . . . . ? Se2 C16 C18 C17 77.0(7) . . . . ? _diffrn_measured_fraction_theta_max 1.001 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.568 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.125 #===END data_AcOPM-EDSTTF _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-acetoxyphenyl)-5-methyl-4',5'ethylenediselenotetrathiafulvalene ; _chemical_name_common AcOPM-EDSTTF _chemical_melting_point 164 _chemical_formula_moiety 'C17 H14 O2 S4 Se2' _chemical_formula_sum 'C17 H14 O2 S4 Se2' _chemical_formula_weight 536.44 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' 'O' 'O' 0.0106 0.0060 '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' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' 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 10.453(1) _cell_length_b 17.267(2) _cell_length_c 11.518(1) _cell_angle_alpha 90.00 _cell_angle_beta 112.10(1) _cell_angle_gamma 90.00 _cell_volume 1926.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 28.0 _exptl_crystal_id 'Ic' _exptl_crystal_description 'needle' _exptl_crystal_colour orange _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.850 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 4.282 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.2017 _exptl_absorpt_correction_T_max 0.6276 _exptl_absorpt_process_details ; Xabs2 - Parkin S., Moezzi B., Hope H., J. Appl. Cryst. 1995, 28, 53-56 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength_id 'X' _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 'Xcalibur Oxford Instrument CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33791 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4550 _reflns_number_gt 3582 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis Oxford Instruments' _computing_cell_refinement 'CrysAlis Oxford Instruments' _computing_data_reduction 'CrysAlis Oxford Instruments' _computing_structure_solution ; SHELXS-97 (Sheldrick, 1997) SIR92 - A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi J. Appl. Cryst., 1993, 26, 343-350 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3 for Windows - L. J. Farrugia J. Appl. Cryst., 1997, 30, 565 ; _computing_publication_material ; WINGX - L. J. Farrugia J. Appl. Cryst., 1999, 32, 837-838 ; _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^)+(0.0579P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4550 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 Se1 Se 0.06907(3) 0.166211(18) -0.01118(3) 0.02729(11) Uani 1 1 d . . . Se2 Se 0.38086(4) 0.21608(2) 0.22426(3) 0.03842(13) Uani 1 1 d . . . S1 S 0.08097(8) 0.02042(4) 0.15143(6) 0.02277(18) Uani 1 1 d . . . S2 S 0.34635(8) 0.05992(5) 0.35054(7) 0.0303(2) Uani 1 1 d . . . S3 S 0.01436(8) -0.09483(4) 0.35534(6) 0.02235(17) Uani 1 1 d . . . S4 S 0.28236(8) -0.05127(5) 0.54472(7) 0.02582(18) Uani 1 1 d . . . O1 O 0.3168(2) -0.12085(16) 1.1240(2) 0.0382(6) Uani 1 1 d . . . O2 O 0.5387(3) -0.1435(2) 1.1607(2) 0.0585(9) Uani 1 1 d . . . C1 C 0.1568(3) 0.10893(17) 0.1372(2) 0.0220(6) Uani 1 1 d . . . C2 C 0.2763(3) 0.12781(19) 0.2302(3) 0.0260(7) Uani 1 1 d . . . C3 C 0.1927(3) 0.00611(17) 0.3077(2) 0.0210(6) Uani 1 1 d . . . C4 C 0.1661(3) -0.04019(17) 0.3895(2) 0.0217(6) Uani 1 1 d . . . C5 C 0.0367(3) -0.10977(16) 0.5131(3) 0.0215(6) Uani 1 1 d . . . C6 C 0.1597(3) -0.09049(16) 0.6004(3) 0.0214(6) Uani 1 1 d . . . C7 C 0.2066(3) -0.09885(16) 0.7384(3) 0.0208(6) Uani 1 1 d . . . C8 C 0.1797(3) -0.16747(18) 0.7903(3) 0.0260(7) Uani 1 1 d . . . H8 H 0.1340 -0.2093 0.7372 0.031 Uiso 1 1 calc R . . C9 C 0.2200(3) -0.17433(19) 0.9196(3) 0.0280(7) Uani 1 1 d . . . H9 H 0.2017 -0.2206 0.9553 0.034 Uiso 1 1 calc R . . C10 C 0.2865(3) -0.1136(2) 0.9947(3) 0.0294(7) Uani 1 1 d . . . C11 C 0.3167(3) -0.0462(2) 0.9466(3) 0.0296(7) Uani 1 1 d . . . H11 H 0.3638 -0.0051 1.0006 0.036 Uiso 1 1 calc R . . C12 C 0.2769(3) -0.03931(19) 0.8172(3) 0.0284(7) Uani 1 1 d . . . H12 H 0.2983 0.0066 0.7828 0.034 Uiso 1 1 calc R . . C13 C 0.4485(4) -0.13717(19) 1.1987(3) 0.0283(7) Uani 1 1 d . . . C14 C 0.4622(4) -0.1457(2) 1.3315(3) 0.0381(9) Uani 1 1 d . . . H14A H 0.3719 -0.1378 1.3373 0.046 Uiso 1 1 calc R . . H14B H 0.5277 -0.1072 1.3833 0.046 Uiso 1 1 calc R . . H14C H 0.4959 -0.1978 1.3612 0.046 Uiso 1 1 calc R . . C15 C -0.0857(3) -0.14443(18) 0.5339(3) 0.0262(7) Uani 1 1 d . . . H15A H -0.1616 -0.1521 0.4529 0.031 Uiso 1 1 calc R . . H15B H -0.1154 -0.1093 0.5857 0.031 Uiso 1 1 calc R . . H15C H -0.0593 -0.1944 0.5765 0.031 Uiso 1 1 calc R . . C16 C 0.3678(4) 0.1944(2) 0.0538(3) 0.0373(9) Uani 1 1 d . . . H16A H 0.4345 0.2278 0.0349 0.045 Uiso 1 1 calc R . . H16B H 0.3949 0.1399 0.0494 0.045 Uiso 1 1 calc R . . C17 C 0.2296(4) 0.2070(3) -0.0425(3) 0.0485(11) Uani 1 1 d . . . H17A H 0.2282 0.1838 -0.1216 0.058 Uiso 1 1 calc R . . H17B H 0.2165 0.2635 -0.0565 0.058 Uiso 1 1 calc R . . 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 Se1 0.0289(2) 0.02799(17) 0.02369(16) 0.00579(12) 0.00840(14) -0.00197(13) Se2 0.0430(2) 0.0436(2) 0.02984(18) -0.00775(14) 0.01506(16) -0.02412(17) S1 0.0237(4) 0.0245(4) 0.0168(3) 0.0016(3) 0.0039(3) -0.0051(3) S2 0.0191(4) 0.0454(5) 0.0231(4) 0.0070(3) 0.0042(3) -0.0081(3) S3 0.0213(4) 0.0236(4) 0.0202(3) 0.0005(3) 0.0055(3) -0.0031(3) S4 0.0172(4) 0.0373(4) 0.0205(3) 0.0076(3) 0.0044(3) -0.0032(3) O1 0.0258(13) 0.0700(18) 0.0203(10) 0.0094(11) 0.0104(10) 0.0094(12) O2 0.0323(15) 0.112(3) 0.0353(14) 0.0117(16) 0.0169(13) 0.0263(17) C1 0.0262(17) 0.0234(14) 0.0182(13) 0.0001(11) 0.0102(12) -0.0036(12) C2 0.0229(17) 0.0334(17) 0.0231(14) 0.0002(12) 0.0102(13) -0.0071(13) C3 0.0163(15) 0.0266(15) 0.0184(13) 0.0017(11) 0.0045(11) -0.0001(11) C4 0.0187(15) 0.0261(15) 0.0172(12) 0.0017(11) 0.0031(11) -0.0004(12) C5 0.0214(15) 0.0198(13) 0.0250(14) 0.0006(11) 0.0108(12) -0.0007(12) C6 0.0240(16) 0.0202(14) 0.0220(13) 0.0021(11) 0.0108(12) 0.0009(12) C7 0.0225(16) 0.0210(14) 0.0219(13) 0.0035(11) 0.0120(12) 0.0036(12) C8 0.0263(17) 0.0270(16) 0.0276(15) 0.0028(12) 0.0136(14) 0.0030(13) C9 0.0252(17) 0.0329(17) 0.0300(16) 0.0106(13) 0.0151(14) 0.0053(13) C10 0.0212(17) 0.048(2) 0.0217(14) 0.0060(14) 0.0106(13) 0.0101(15) C11 0.0257(17) 0.0372(18) 0.0232(14) -0.0035(13) 0.0060(13) -0.0010(14) C12 0.0260(17) 0.0319(16) 0.0253(15) 0.0054(13) 0.0074(13) -0.0013(13) C13 0.0280(18) 0.0284(16) 0.0261(15) 0.0009(12) 0.0074(14) 0.0057(13) C14 0.041(2) 0.048(2) 0.0247(16) 0.0064(15) 0.0113(15) 0.0073(17) C15 0.0214(16) 0.0247(15) 0.0394(17) -0.0010(13) 0.0192(14) -0.0045(12) C16 0.042(2) 0.045(2) 0.0340(17) -0.0062(15) 0.0246(17) -0.0174(17) C17 0.041(2) 0.075(3) 0.0353(19) 0.0143(19) 0.0211(18) -0.008(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 Se1 C1 1.887(3) . ? Se1 C17 1.974(4) . ? Se2 C2 1.892(3) . ? Se2 C16 1.952(3) . ? S1 C3 1.756(3) . ? S1 C1 1.757(3) . ? S2 C2 1.752(3) . ? S2 C3 1.757(3) . ? S3 C4 1.758(3) . ? S3 C5 1.761(3) . ? S4 C4 1.753(3) . ? S4 C6 1.770(3) . ? O1 C13 1.350(4) . ? O1 C10 1.407(3) . ? O2 C13 1.185(4) . ? C1 C2 1.344(4) . ? C3 C4 1.342(4) . ? C5 C6 1.343(4) . ? C5 C15 1.511(4) . ? C6 C7 1.484(4) . ? C7 C12 1.385(4) . ? C7 C8 1.402(4) . ? C8 C9 1.392(4) . ? C9 C10 1.371(5) . ? C10 C11 1.375(5) . ? C11 C12 1.393(4) . ? C13 C14 1.489(4) . ? C16 C17 1.469(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 C1 Se1 C17 101.28(15) . . ? C2 Se2 C16 93.41(14) . . ? C3 S1 C1 93.93(13) . . ? C2 S2 C3 93.78(14) . . ? C4 S3 C5 95.13(13) . . ? C4 S4 C6 95.32(14) . . ? C13 O1 C10 117.6(3) . . ? C2 C1 S1 116.9(2) . . ? C2 C1 Se1 125.7(2) . . ? S1 C1 Se1 117.24(15) . . ? C1 C2 S2 117.1(2) . . ? C1 C2 Se2 122.9(2) . . ? S2 C2 Se2 119.52(16) . . ? C4 C3 S1 124.7(2) . . ? C4 C3 S2 121.8(2) . . ? S1 C3 S2 113.48(16) . . ? C3 C4 S4 122.2(2) . . ? C3 C4 S3 124.8(2) . . ? S4 C4 S3 112.98(16) . . ? C6 C5 C15 127.5(3) . . ? C6 C5 S3 117.0(2) . . ? C15 C5 S3 115.5(2) . . ? C5 C6 C7 128.0(3) . . ? C5 C6 S4 116.3(2) . . ? C7 C6 S4 115.7(2) . . ? C12 C7 C8 119.4(3) . . ? C12 C7 C6 120.6(3) . . ? C8 C7 C6 120.0(3) . . ? C9 C8 C7 119.9(3) . . ? C10 C9 C8 119.2(3) . . ? C9 C10 C11 122.1(3) . . ? C9 C10 O1 117.3(3) . . ? C11 C10 O1 120.5(3) . . ? C10 C11 C12 118.8(3) . . ? C7 C12 C11 120.5(3) . . ? O2 C13 O1 123.1(3) . . ? O2 C13 C14 126.0(3) . . ? O1 C13 C14 110.9(3) . . ? C17 C16 Se2 114.1(3) . . ? C16 C17 Se1 118.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 S1 C1 C2 10.7(3) . . . . ? C3 S1 C1 Se1 -172.80(18) . . . . ? C17 Se1 C1 C2 34.8(3) . . . . ? C17 Se1 C1 S1 -141.4(2) . . . . ? S1 C1 C2 S2 3.0(4) . . . . ? Se1 C1 C2 S2 -173.22(17) . . . . ? S1 C1 C2 Se2 174.34(17) . . . . ? Se1 C1 C2 Se2 -1.8(4) . . . . ? C3 S2 C2 C1 -14.9(3) . . . . ? C3 S2 C2 Se2 173.4(2) . . . . ? C16 Se2 C2 C1 -47.0(3) . . . . ? C16 Se2 C2 S2 124.2(2) . . . . ? C1 S1 C3 C4 158.8(3) . . . . ? C1 S1 C3 S2 -20.5(2) . . . . ? C2 S2 C3 C4 -157.6(3) . . . . ? C2 S2 C3 S1 21.7(2) . . . . ? S1 C3 C4 S4 -179.63(17) . . . . ? S2 C3 C4 S4 -0.5(4) . . . . ? S1 C3 C4 S3 -0.2(4) . . . . ? S2 C3 C4 S3 179.01(17) . . . . ? C6 S4 C4 C3 162.4(3) . . . . ? C6 S4 C4 S3 -17.16(19) . . . . ? C5 S3 C4 C3 -162.0(3) . . . . ? C5 S3 C4 S4 17.49(19) . . . . ? C4 S3 C5 C6 -11.2(3) . . . . ? C4 S3 C5 C15 169.8(2) . . . . ? C15 C5 C6 C7 0.5(5) . . . . ? S3 C5 C6 C7 -178.4(2) . . . . ? C15 C5 C6 S4 179.7(2) . . . . ? S3 C5 C6 S4 0.8(3) . . . . ? C4 S4 C6 C5 10.0(3) . . . . ? C4 S4 C6 C7 -170.7(2) . . . . ? C5 C6 C7 C12 -135.5(3) . . . . ? S4 C6 C7 C12 45.3(4) . . . . ? C5 C6 C7 C8 44.4(5) . . . . ? S4 C6 C7 C8 -134.8(3) . . . . ? C12 C7 C8 C9 1.9(5) . . . . ? C6 C7 C8 C9 -178.0(3) . . . . ? C7 C8 C9 C10 -0.3(5) . . . . ? C8 C9 C10 C11 -1.1(5) . . . . ? C8 C9 C10 O1 175.7(3) . . . . ? C13 O1 C10 C9 103.4(4) . . . . ? C13 O1 C10 C11 -79.8(4) . . . . ? C9 C10 C11 C12 0.8(5) . . . . ? O1 C10 C11 C12 -175.9(3) . . . . ? C8 C7 C12 C11 -2.2(5) . . . . ? C6 C7 C12 C11 177.8(3) . . . . ? C10 C11 C12 C7 0.9(5) . . . . ? C10 O1 C13 O2 2.0(5) . . . . ? C10 O1 C13 C14 -178.0(3) . . . . ? C2 Se2 C16 C17 71.1(3) . . . . ? Se2 C16 C17 Se1 -45.4(4) . . . . ? C1 Se1 C17 C16 -7.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.153 _refine_diff_density_min -1.155 _refine_diff_density_rms 0.101 #===END data_(AcOPM-EDSTTF)2-TCNQ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (AcOPM-EDSTTF)2-TCNQ _chemical_melting_point 210 _chemical_formula_moiety 'C23 H16 N2 O2 S4 Se2' _chemical_formula_sum 'C23 H16 N2 O2 S4 Se2' _chemical_formula_weight 638.54 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'I 1 2/a 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, 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 30.154(8) _cell_length_b 4.052(4) _cell_length_c 39.317(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.40(3) _cell_angle_gamma 90.00 _cell_volume 4802(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_id '(Ic)2TCNQ' _exptl_crystal_description 'plate' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.766 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 3.453 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166 ; _exptl_absorpt_correction_T_min 0.3287 _exptl_absorpt_correction_T_max 0.8414 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength_id 'X' _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 'Enraf-Nonius CAD4' _diffrn_measurement_method 'omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5512 _diffrn_reflns_av_R_equivalents 0.0757 _diffrn_reflns_av_sigmaI/netI 0.0814 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 21.98 _reflns_number_total 2945 _reflns_number_gt 1715 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4-Express' _computing_cell_refinement 'CAD4-Express' _computing_data_reduction ; WINGX - L. J. Farrugia J. Appl. Cryst., 1999, 32, 837-838 ; _computing_structure_solution ; SHELXS-97 (Sheldrick, 1997) SIR92 - A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi J. Appl. Cryst., 1993, 26, 343-350 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3 for Windows - L. J. Farrugia J. Appl. Cryst., 1997, 30, 565 ; _computing_publication_material ; WINGX - L. J. Farrugia J. Appl. Cryst., 1999, 32, 837-838 ; _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^)+(0.0691P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2945 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1073 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 Se1 Se 0.37981(3) 0.1408(3) 0.37289(2) 0.0492(3) Uani 1 1 d . . . Se2 Se 0.48579(3) 0.1563(3) 0.41111(2) 0.0533(3) Uani 1 1 d . . . S1 S 0.35158(6) 0.5121(6) 0.43740(5) 0.0445(6) Uani 1 1 d . . . S2 S 0.43949(6) 0.5036(6) 0.47086(5) 0.0447(6) Uani 1 1 d . . . S3 S 0.31128(6) 0.8375(7) 0.50606(5) 0.0485(6) Uani 1 1 d . . . S4 S 0.39896(6) 0.8077(6) 0.53855(5) 0.0446(6) Uani 1 1 d . . . O1 O 0.39942(16) 1.1435(16) 0.70225(11) 0.0492(15) Uani 1 1 d . . . O2 O 0.4637(2) 0.878(2) 0.70006(14) 0.092(3) Uani 1 1 d . . . C1 C 0.3946(2) 0.319(2) 0.41582(17) 0.0356(19) Uiso 1 1 d . . . C2 C 0.4338(2) 0.318(2) 0.43080(18) 0.039(2) Uiso 1 1 d . . . C3 C 0.3833(2) 0.598(2) 0.47391(18) 0.038(2) Uiso 1 1 d . . . C4 C 0.3665(2) 0.731(2) 0.50232(17) 0.0352(19) Uiso 1 1 d . . . C5 C 0.3145(2) 0.951(2) 0.54854(18) 0.042(2) Uiso 1 1 d . . . C6 C 0.3550(2) 0.934(2) 0.56421(17) 0.037(2) Uiso 1 1 d . . . C7 C 0.3667(2) 0.997(2) 0.59990(18) 0.0352(19) Uiso 1 1 d . . . C8 C 0.3411(2) 0.875(2) 0.62521(18) 0.042(2) Uiso 1 1 d . . . H8 H 0.3153 0.7614 0.6193 0.051 Uiso 1 1 calc R . . C9 C 0.3522(2) 0.915(2) 0.65948(18) 0.040(2) Uiso 1 1 d . . . H9 H 0.3343 0.8297 0.6763 0.048 Uiso 1 1 calc R . . C10 C 0.3905(2) 1.084(2) 0.66756(18) 0.039(2) Uiso 1 1 d . . . C11 C 0.4164(3) 1.210(2) 0.64347(17) 0.042(2) Uiso 1 1 d . . . H11 H 0.4421 1.3246 0.6496 0.050 Uiso 1 1 calc R . . C12 C 0.4047(2) 1.169(2) 0.60930(17) 0.0370(19) Uiso 1 1 d . . . H12 H 0.4225 1.2574 0.5926 0.044 Uiso 1 1 calc R . . C13 C 0.4378(3) 1.031(2) 0.7161(2) 0.043(2) Uiso 1 1 d . . . C14 C 0.4425(3) 1.122(2) 0.75242(19) 0.056(2) Uiso 1 1 d . . . H14A H 0.4167 1.2417 0.7591 0.067 Uiso 1 1 calc R . . H14B H 0.4683 1.2587 0.7557 0.067 Uiso 1 1 calc R . . H14C H 0.4457 0.9260 0.7660 0.067 Uiso 1 1 calc R . . C15 C 0.2725(2) 1.078(2) 0.5637(2) 0.052(2) Uiso 1 1 d . . . H15A H 0.2486 1.0611 0.5472 0.063 Uiso 1 1 calc R . . H15B H 0.2764 1.3040 0.5702 0.063 Uiso 1 1 calc R . . H15C H 0.2657 0.9482 0.5834 0.063 Uiso 1 1 calc R . . C16 C 0.4729(3) 0.344(3) 0.36652(19) 0.057(2) Uiso 1 1 d . . . H16A H 0.4719 0.5820 0.3691 0.068 Uiso 1 1 calc R . . H16B H 0.4979 0.2948 0.3523 0.068 Uiso 1 1 calc R . . C17 C 0.4327(3) 0.246(2) 0.3478(2) 0.058(3) Uiso 1 1 d . . . H17A H 0.4400 0.0538 0.3343 0.070 Uiso 1 1 calc R . . H17B H 0.4251 0.4221 0.3320 0.070 Uiso 1 1 calc R . . N1 N 0.3696(2) 0.857(2) 0.29552(17) 0.063(2) Uani 1 1 d . . . N2 N 0.2630(2) 0.598(3) 0.3633(2) 0.088(3) Uani 1 1 d . . . C20 C 0.2942(2) 0.581(2) 0.30426(18) 0.041(2) Uiso 1 1 d . . . C21 C 0.3365(3) 0.731(2) 0.29931(18) 0.044(2) Uiso 1 1 d . . . C22 C 0.2766(3) 0.594(2) 0.3371(2) 0.052(2) Uiso 1 1 d . . . C23 C 0.2728(2) 0.411(2) 0.27695(18) 0.041(2) Uiso 1 1 d . . . C24 C 0.2916(3) 0.379(2) 0.24447(18) 0.043(2) Uiso 1 1 d . . . H24 H 0.3196 0.4660 0.2408 0.052 Uiso 1 1 calc R . . C25 C 0.2299(2) 0.275(2) 0.28112(19) 0.045(2) Uiso 1 1 d . . . H25 H 0.2165 0.2934 0.3021 0.054 Uiso 1 1 calc R . . 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 Se1 0.0540(5) 0.0494(7) 0.0443(5) -0.0115(5) 0.0020(4) -0.0111(5) Se2 0.0489(5) 0.0476(7) 0.0634(6) -0.0126(5) 0.0024(4) 0.0113(5) S1 0.0387(11) 0.0556(16) 0.0391(11) -0.0066(11) -0.0028(9) -0.0003(12) S2 0.0391(11) 0.0539(16) 0.0408(11) -0.0074(12) -0.0041(9) 0.0034(12) S3 0.0397(12) 0.0667(17) 0.0386(11) -0.0074(13) -0.0061(9) 0.0067(13) S4 0.0354(11) 0.0635(17) 0.0349(10) -0.0049(12) -0.0002(9) 0.0050(12) O1 0.045(3) 0.068(4) 0.035(3) -0.012(3) -0.005(2) 0.009(3) O2 0.076(4) 0.150(8) 0.048(4) -0.027(5) -0.013(3) 0.059(5) N1 0.052(4) 0.073(6) 0.065(5) -0.013(5) 0.002(4) -0.018(5) N2 0.056(5) 0.128(9) 0.081(6) -0.027(6) 0.015(4) -0.001(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 Se1 C1 1.882(7) . ? Se1 C17 1.944(8) . ? Se2 C2 1.882(7) . ? Se2 C16 1.940(8) . ? S1 C3 1.741(7) . ? S1 C1 1.753(8) . ? S2 C3 1.744(7) . ? S2 C2 1.752(8) . ? S3 C4 1.729(7) . ? S3 C5 1.734(7) . ? S4 C4 1.738(7) . ? S4 C6 1.761(7) . ? O1 C13 1.345(9) . ? O1 C10 1.405(8) . ? O2 C13 1.190(9) . ? C1 C2 1.307(10) . ? C3 C4 1.351(10) . ? C5 C6 1.356(10) . ? C5 C15 1.503(10) . ? C6 C7 1.461(10) . ? C7 C8 1.365(10) . ? C7 C12 1.385(10) . ? C8 C9 1.390(10) . ? C9 C10 1.376(10) . ? C10 C11 1.344(10) . ? C11 C12 1.392(9) . ? C13 C14 1.480(11) . ? C16 C17 1.458(11) . ? N1 C21 1.134(9) . ? N2 C22 1.117(10) . ? C20 C22 1.408(11) . ? C20 C23 1.419(10) . ? C20 C21 1.432(11) . ? C23 C24 1.417(10) . ? C23 C25 1.420(10) . ? C24 C25 1.340(10) 7 ? C25 C24 1.340(10) 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 C1 Se1 C17 101.0(3) . . ? C2 Se2 C16 94.9(3) . . ? C3 S1 C1 95.2(3) . . ? C3 S2 C2 94.7(4) . . ? C4 S3 C5 96.7(4) . . ? C4 S4 C6 96.1(3) . . ? C13 O1 C10 118.4(6) . . ? C2 C1 S1 117.0(6) . . ? C2 C1 Se1 126.6(6) . . ? S1 C1 Se1 116.4(4) . . ? C1 C2 S2 118.2(6) . . ? C1 C2 Se2 124.6(6) . . ? S2 C2 Se2 117.1(4) . . ? C4 C3 S1 123.6(6) . . ? C4 C3 S2 121.9(6) . . ? S1 C3 S2 114.5(4) . . ? C3 C4 S3 123.4(6) . . ? C3 C4 S4 122.4(6) . . ? S3 C4 S4 114.2(4) . . ? C6 C5 C15 126.6(7) . . ? C6 C5 S3 117.0(6) . . ? C15 C5 S3 116.4(5) . . ? C5 C6 C7 128.3(7) . . ? C5 C6 S4 115.8(5) . . ? C7 C6 S4 115.8(5) . . ? C8 C7 C12 117.8(7) . . ? C8 C7 C6 120.6(7) . . ? C12 C7 C6 121.6(6) . . ? C7 C8 C9 122.5(7) . . ? C10 C9 C8 117.7(7) . . ? C11 C10 C9 121.8(7) . . ? C11 C10 O1 121.1(7) . . ? C9 C10 O1 116.8(6) . . ? C10 C11 C12 119.6(7) . . ? C7 C12 C11 120.7(7) . . ? O2 C13 O1 122.0(7) . . ? O2 C13 C14 126.5(8) . . ? O1 C13 C14 111.5(7) . . ? C17 C16 Se2 119.6(7) . . ? C16 C17 Se1 119.1(6) . . ? C22 C20 C23 122.5(7) . . ? C22 C20 C21 117.7(7) . . ? C23 C20 C21 119.7(7) . . ? N1 C21 C20 178.5(10) . . ? N2 C22 C20 178.4(12) . . ? C24 C23 C20 122.9(7) . . ? C24 C23 C25 117.0(7) . . ? C20 C23 C25 120.1(7) . . ? C25 C24 C23 121.6(7) 7 . ? C24 C25 C23 121.5(7) 7 . ? 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 C3 S1 C1 C2 -4.3(8) . . . . ? C3 S1 C1 Se1 176.9(5) . . . . ? C17 Se1 C1 C2 -37.0(9) . . . . ? C17 Se1 C1 S1 141.7(5) . . . . ? S1 C1 C2 S2 0.7(10) . . . . ? Se1 C1 C2 S2 179.4(4) . . . . ? S1 C1 C2 Se2 -174.9(4) . . . . ? Se1 C1 C2 Se2 3.9(13) . . . . ? C3 S2 C2 C1 3.3(8) . . . . ? C3 S2 C2 Se2 179.1(5) . . . . ? C16 Se2 C2 C1 41.4(9) . . . . ? C16 Se2 C2 S2 -134.2(5) . . . . ? C1 S1 C3 C4 -174.7(7) . . . . ? C1 S1 C3 S2 6.3(5) . . . . ? C2 S2 C3 C4 175.0(7) . . . . ? C2 S2 C3 S1 -6.0(5) . . . . ? S1 C3 C4 S3 -0.6(11) . . . . ? S2 C3 C4 S3 178.3(5) . . . . ? S1 C3 C4 S4 179.1(5) . . . . ? S2 C3 C4 S4 -2.0(11) . . . . ? C5 S3 C4 C3 175.3(7) . . . . ? C5 S3 C4 S4 -4.4(6) . . . . ? C6 S4 C4 C3 -174.7(7) . . . . ? C6 S4 C4 S3 5.0(5) . . . . ? C4 S3 C5 C6 1.7(8) . . . . ? C4 S3 C5 C15 178.3(7) . . . . ? C15 C5 C6 C7 7.4(15) . . . . ? S3 C5 C6 C7 -176.3(7) . . . . ? C15 C5 C6 S4 -174.6(7) . . . . ? S3 C5 C6 S4 1.6(10) . . . . ? C4 S4 C6 C5 -4.0(7) . . . . ? C4 S4 C6 C7 174.2(7) . . . . ? C5 C6 C7 C8 44.0(14) . . . . ? S4 C6 C7 C8 -134.0(7) . . . . ? C5 C6 C7 C12 -138.6(9) . . . . ? S4 C6 C7 C12 43.4(11) . . . . ? C12 C7 C8 C9 -0.8(12) . . . . ? C6 C7 C8 C9 176.6(8) . . . . ? C7 C8 C9 C10 0.0(13) . . . . ? C8 C9 C10 C11 0.6(13) . . . . ? C8 C9 C10 O1 175.2(7) . . . . ? C13 O1 C10 C11 -62.9(11) . . . . ? C13 O1 C10 C9 122.5(8) . . . . ? C9 C10 C11 C12 -0.4(13) . . . . ? O1 C10 C11 C12 -174.8(7) . . . . ? C8 C7 C12 C11 1.0(12) . . . . ? C6 C7 C12 C11 -176.4(8) . . . . ? C10 C11 C12 C7 -0.4(13) . . . . ? C10 O1 C13 O2 -1.8(13) . . . . ? C10 O1 C13 C14 178.5(7) . . . . ? C2 Se2 C16 C17 -60.4(8) . . . . ? Se2 C16 C17 Se1 33.3(11) . . . . ? C1 Se1 C17 C16 15.0(9) . . . . ? C22 C20 C21 N1 -66(33) . . . . ? C23 C20 C21 N1 117(33) . . . . ? C23 C20 C22 N2 83(40) . . . . ? C21 C20 C22 N2 -94(40) . . . . ? C22 C20 C23 C24 -175.9(8) . . . . ? C21 C20 C23 C24 0.9(13) . . . . ? C22 C20 C23 C25 6.4(13) . . . . ? C21 C20 C23 C25 -176.8(8) . . . . ? C20 C23 C24 C25 -178.2(8) . . . 7 ? C25 C23 C24 C25 -0.4(14) . . . 7 ? C24 C23 C25 C24 0.4(14) . . . 7 ? C20 C23 C25 C24 178.2(8) . . . 7 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 21.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.502 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.106