# Supplementary Material (ESI) for Chemical Science # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Chemical Science' _journal_coden_Cambridge 1475 _publ_contact_author_name 'Takimiya, Kazuo' _publ_contact_author_email ktakimi@hiroshima-u.ac.jp _publ_section_title ; Unique Three-Dimensional (3D) Molecular Array in Dimethyl-DNTT Crystals: a New Approach to 3D Organic Semiconductors ; loop_ _publ_author_name K.Takimiya E.Miyazaki M.J.Kang T.Yamamoto S.Shinamura # Attachment '- DMeDNTTs_rev.cif' data_2,9-DMeDNTT _database_code_depnum_ccdc_archive 'CCDC 763568' #TrackingRef '- DMeDNTTs_rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,8-DMeDNTT ; _chemical_name_common 2,8-DMeDNTT _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 S2' _chemical_formula_sum 'C24 H16 S2' _chemical_formula_weight 368.49 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' 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 1' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.686(12) _cell_length_b 7.737(7) _cell_length_c 10.674(11) _cell_angle_alpha 90 _cell_angle_beta 114.187(5) _cell_angle_gamma 90 _cell_volume 880.4(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2572 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description Platelet _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.020 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.307 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.71 _diffrn_standards_number 7119 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7063 _diffrn_reflns_av_R_equivalents 0.1069 _diffrn_reflns_av_sigmaI/netI 0.1569 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3857 _reflns_number_gt 1949 _reflns_threshold_expression >2sigma(I) _computing_data_collection CRYSTALCLEAR _computing_cell_refinement CRYSTALCLEAR _computing_data_reduction 'teXsan Ver. 1.11' _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^)+(0.0789P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.52(19) _refine_ls_number_reflns 3857 _refine_ls_number_parameters 235 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1027 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1929 _refine_ls_wR_factor_gt 0.1702 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _refine_ls_shift/su_max 0.045 _refine_ls_shift/su_mean 0.002 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 0.67123(12) 0.5761(2) 0.92480(16) 0.0504(4) Uani 1 1 d . . . S2 S 1.01682(13) 0.7934(2) 0.97358(16) 0.0529(4) Uani 1 1 d . . . C1 C 0.6604(4) 0.6220(7) 0.7587(6) 0.0423(14) Uani 1 1 d . . . C2 C 0.5629(4) 0.5883(8) 0.6384(6) 0.0420(12) Uani 1 1 d . . . C3 C 0.5681(4) 0.6297(6) 0.5118(6) 0.0386(13) Uani 1 1 d . . . C4 C 0.4716(5) 0.5902(8) 0.3833(6) 0.0473(13) Uani 1 1 d . . . C5 C 0.4753(5) 0.6271(7) 0.2608(7) 0.0526(15) Uani 1 1 d . . . C6 C 0.5851(6) 0.7147(8) 0.2646(6) 0.0519(15) Uani 1 1 d . . . C7 C 0.6809(5) 0.7522(8) 0.3842(7) 0.0499(15) Uani 1 1 d . . . C8 C 0.6778(4) 0.7118(6) 0.5116(6) 0.0399(12) Uani 1 1 d . . . C9 C 0.7807(5) 0.7480(7) 0.6404(6) 0.0437(14) Uani 1 1 d . . . C10 C 0.7736(5) 0.7009(6) 0.7632(6) 0.0411(12) Uani 1 1 d . . . C11 C 1.0280(4) 0.7447(6) 1.1385(6) 0.0419(13) Uani 1 1 d . . . C12 C 1.1308(4) 0.7690(7) 1.2588(6) 0.0440(13) Uani 1 1 d . . . C13 C 1.1255(5) 0.7204(7) 1.3851(6) 0.0416(12) Uani 1 1 d . . . C14 C 1.2285(5) 0.7509(7) 1.5144(6) 0.0454(14) Uani 1 1 d . . . C15 C 1.2229(5) 0.7037(7) 1.6345(6) 0.0465(13) Uani 1 1 d . . . C16 C 1.1131(6) 0.6258(8) 1.6332(7) 0.0536(16) Uani 1 1 d . . . C17 C 1.0130(5) 0.5959(8) 1.5131(6) 0.0478(14) Uani 1 1 d . . . C18 C 1.0142(5) 0.6437(7) 1.3839(6) 0.0417(13) Uani 1 1 d . . . C19 C 0.9100(4) 0.6183(7) 1.2585(6) 0.0445(14) Uani 1 1 d . . . C20 C 0.9138(4) 0.6692(6) 1.1364(6) 0.0410(13) Uani 1 1 d . . . C21 C 0.8238(4) 0.6587(7) 0.9967(6) 0.0442(13) Uani 1 1 d . . . C22 C 0.8631(4) 0.7179(7) 0.9014(6) 0.0421(13) Uani 1 1 d . . . C23 C 0.3708(6) 0.5793(9) 0.1252(7) 0.0646(16) Uani 1 1 d . . . C24 C 1.3314(5) 0.7368(8) 1.7704(7) 0.0592(17) Uani 1 1 d . . . H1 H 0.4885 0.5339 0.6379 0.051 Uiso 1 1 d . . . H2 H 0.3987 0.5317 0.3835 0.059 Uiso 1 1 d . . . H3 H 0.5910 0.7463 0.1808 0.063 Uiso 1 1 d . . . H4 H 0.7529 0.8096 0.3806 0.060 Uiso 1 1 d . . . H5 H 0.8526 0.8041 0.6409 0.054 Uiso 1 1 d . . . H6 H 1.2058 0.8160 1.2567 0.054 Uiso 1 1 d . . . H7 H 1.3029 0.8053 1.5145 0.055 Uiso 1 1 d . . . H8 H 1.1108 0.5940 1.7199 0.063 Uiso 1 1 d . . . H9 H 0.9388 0.5439 1.5141 0.059 Uiso 1 1 d . . . H10 H 0.8348 0.5674 1.2582 0.052 Uiso 1 1 d . . . H11 H 0.3634 0.4555 0.1198 0.076 Uiso 1 1 d . . . H12 H 0.2959 0.6292 0.1160 0.076 Uiso 1 1 d . . . H13 H 0.3932 0.6167 0.0521 0.076 Uiso 1 1 d . . . H14 H 1.3987 0.7922 1.7563 0.074 Uiso 1 1 d . . . H15 H 1.3063 0.8135 1.8261 0.074 Uiso 1 1 d . . . H16 H 1.3613 0.6329 1.8196 0.074 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 S1 0.0429(7) 0.0558(8) 0.0544(9) 0.0040(8) 0.0218(6) -0.0068(6) S2 0.0474(7) 0.0575(10) 0.0558(10) 0.0046(7) 0.0232(6) -0.0102(7) C1 0.037(3) 0.041(3) 0.057(4) 0.010(3) 0.027(3) -0.002(2) C2 0.036(2) 0.041(3) 0.052(3) 0.005(3) 0.021(2) -0.001(2) C3 0.036(2) 0.033(3) 0.050(4) 0.004(2) 0.021(2) 0.002(2) C4 0.054(3) 0.042(3) 0.051(4) -0.001(3) 0.026(3) -0.002(3) C5 0.062(4) 0.046(3) 0.055(4) -0.001(3) 0.028(3) -0.001(3) C6 0.062(3) 0.057(4) 0.045(4) 0.001(3) 0.030(3) 0.004(3) C7 0.054(3) 0.045(4) 0.063(4) 0.001(3) 0.037(3) 0.003(3) C8 0.038(2) 0.034(3) 0.051(4) 0.005(2) 0.022(2) 0.001(2) C9 0.046(3) 0.040(3) 0.052(4) 0.000(3) 0.027(3) 0.001(2) C10 0.043(3) 0.029(2) 0.056(4) 0.003(3) 0.025(3) -0.002(2) C11 0.038(3) 0.040(3) 0.052(3) 0.005(2) 0.023(2) -0.004(2) C12 0.037(2) 0.043(3) 0.056(4) 0.005(3) 0.023(2) -0.005(2) C13 0.042(3) 0.034(3) 0.051(4) 0.000(2) 0.022(3) 0.001(2) C14 0.038(3) 0.047(4) 0.051(4) -0.003(3) 0.018(2) 0.002(2) C15 0.045(3) 0.043(3) 0.048(4) -0.003(3) 0.016(2) 0.005(2) C16 0.054(3) 0.057(4) 0.055(4) 0.008(3) 0.028(3) 0.006(3) C17 0.052(3) 0.047(3) 0.051(3) 0.006(3) 0.028(3) -0.002(3) C18 0.044(3) 0.038(3) 0.051(4) -0.004(2) 0.027(3) -0.002(2) C19 0.036(3) 0.041(3) 0.061(4) 0.004(3) 0.023(2) -0.004(2) C20 0.042(3) 0.030(3) 0.058(4) 0.002(2) 0.027(3) 0.005(2) C21 0.037(3) 0.044(3) 0.054(4) 0.001(3) 0.022(2) 0.004(2) C22 0.038(2) 0.041(3) 0.050(4) 0.003(3) 0.021(2) 0.003(2) C23 0.084(4) 0.052(3) 0.056(4) 0.007(4) 0.027(3) 0.011(4) C24 0.051(3) 0.067(4) 0.057(4) -0.006(3) 0.019(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C21 1.748(5) . yes S1 C1 1.761(6) . yes S2 C22 1.740(5) . yes S2 C11 1.752(6) . yes C1 C2 1.347(7) . yes C1 C10 1.440(6) . yes C2 C3 1.414(8) . yes C3 C4 1.407(8) . yes C3 C8 1.432(6) . yes C4 C5 1.357(8) . yes C5 C6 1.437(8) . yes C5 C23 1.508(8) . yes C6 C7 1.340(8) . yes C7 C8 1.410(8) . yes C8 C9 1.435(7) . yes C9 C10 1.396(8) . yes C10 C22 1.422(8) . yes C11 C12 1.365(7) . yes C11 C20 1.448(6) . yes C12 C13 1.426(8) . yes C13 C18 1.425(7) . yes C13 C14 1.430(7) . yes C14 C15 1.361(8) . yes C15 C16 1.412(8) . yes C15 C24 1.507(8) . yes C16 C17 1.355(8) . yes C17 C18 1.434(8) . yes C18 C19 1.406(8) . yes C19 C20 1.380(8) . yes C20 C21 1.432(7) . yes C21 C22 1.357(6) . yes 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 C21 S1 C1 90.5(3) . . yes C22 S2 C11 90.6(3) . . yes C2 C1 C10 121.4(5) . . yes C2 C1 S1 127.2(4) . . yes C10 C1 S1 111.4(4) . . yes C1 C2 C3 121.1(5) . . yes C4 C3 C2 123.4(5) . . yes C4 C3 C8 117.1(5) . . yes C2 C3 C8 119.4(5) . . yes C5 C4 C3 124.3(5) . . yes C4 C5 C6 116.9(5) . . yes C4 C5 C23 122.7(5) . . yes C6 C5 C23 120.3(6) . . yes C7 C6 C5 121.1(6) . . yes C6 C7 C8 122.0(5) . . yes C7 C8 C3 118.5(5) . . yes C7 C8 C9 122.6(5) . . yes C3 C8 C9 119.0(5) . . yes C10 C9 C8 120.0(5) . . yes C9 C10 C22 130.4(5) . . yes C9 C10 C1 119.1(5) . . yes C22 C10 C1 110.5(5) . . yes C12 C11 C20 121.4(5) . . yes C12 C11 S2 126.1(4) . . yes C20 C11 S2 112.5(4) . . yes C11 C12 C13 119.4(5) . . yes C12 C13 C18 119.6(5) . . yes C12 C13 C14 121.6(5) . . yes C18 C13 C14 118.8(5) . . yes C15 C14 C13 121.2(5) . . yes C14 C15 C16 120.0(5) . . yes C14 C15 C24 121.0(5) . . yes C16 C15 C24 119.0(5) . . yes C17 C16 C15 120.7(6) . . yes C16 C17 C18 121.4(5) . . yes C19 C18 C13 119.9(5) . . yes C19 C18 C17 122.2(5) . . yes C13 C18 C17 117.8(5) . . yes C20 C19 C18 120.5(5) . . yes C19 C20 C21 132.3(5) . . yes C19 C20 C11 119.1(5) . . yes C21 C20 C11 108.6(5) . . yes C22 C21 C20 115.6(4) . . yes C22 C21 S1 113.1(4) . . yes C20 C21 S1 131.3(4) . . yes C21 C22 C10 114.5(4) . . yes C21 C22 S2 112.8(4) . . yes C10 C22 S2 132.7(4) . . yes 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 C21 S1 C1 C2 178.2(6) . . . . yes C21 S1 C1 C10 -0.6(4) . . . . yes C10 C1 C2 C3 -0.2(9) . . . . yes S1 C1 C2 C3 -178.8(4) . . . . yes C1 C2 C3 C4 177.0(5) . . . . yes C1 C2 C3 C8 -1.2(8) . . . . yes C2 C3 C4 C5 -179.2(5) . . . . yes C8 C3 C4 C5 -1.1(9) . . . . yes C3 C4 C5 C6 -1.0(9) . . . . yes C3 C4 C5 C23 178.7(5) . . . . yes C4 C5 C6 C7 2.3(9) . . . . yes C23 C5 C6 C7 -177.4(6) . . . . yes C5 C6 C7 C8 -1.5(10) . . . . yes C6 C7 C8 C3 -0.6(8) . . . . yes C6 C7 C8 C9 178.7(5) . . . . yes C4 C3 C8 C7 1.8(7) . . . . yes C2 C3 C8 C7 -179.9(5) . . . . yes C4 C3 C8 C9 -177.5(5) . . . . yes C2 C3 C8 C9 0.8(8) . . . . yes C7 C8 C9 C10 -178.3(5) . . . . yes C3 C8 C9 C10 1.0(8) . . . . yes C8 C9 C10 C22 177.9(5) . . . . yes C8 C9 C10 C1 -2.3(8) . . . . yes C2 C1 C10 C9 2.0(8) . . . . yes S1 C1 C10 C9 -179.2(4) . . . . yes C2 C1 C10 C22 -178.2(5) . . . . yes S1 C1 C10 C22 0.6(6) . . . . yes C22 S2 C11 C12 179.3(5) . . . . yes C22 S2 C11 C20 0.6(4) . . . . yes C20 C11 C12 C13 -0.5(8) . . . . yes S2 C11 C12 C13 -179.1(4) . . . . yes C11 C12 C13 C18 1.4(8) . . . . yes C11 C12 C13 C14 -176.9(5) . . . . yes C12 C13 C14 C15 -179.8(5) . . . . yes C18 C13 C14 C15 1.9(8) . . . . yes C13 C14 C15 C16 -1.2(9) . . . . yes C13 C14 C15 C24 -179.7(5) . . . . yes C14 C15 C16 C17 0.6(10) . . . . yes C24 C15 C16 C17 179.1(6) . . . . yes C15 C16 C17 C18 -0.7(10) . . . . yes C12 C13 C18 C19 -0.7(8) . . . . yes C14 C13 C18 C19 177.6(5) . . . . yes C12 C13 C18 C17 179.7(5) . . . . yes C14 C13 C18 C17 -2.0(7) . . . . yes C16 C17 C18 C19 -178.2(6) . . . . yes C16 C17 C18 C13 1.4(9) . . . . yes C13 C18 C19 C20 -0.9(8) . . . . yes C17 C18 C19 C20 178.7(5) . . . . yes C18 C19 C20 C21 179.7(5) . . . . yes C18 C19 C20 C11 1.8(7) . . . . yes C12 C11 C20 C19 -1.1(8) . . . . yes S2 C11 C20 C19 177.7(4) . . . . yes C12 C11 C20 C21 -179.4(5) . . . . yes S2 C11 C20 C21 -0.6(5) . . . . yes C19 C20 C21 C22 -177.7(5) . . . . yes C11 C20 C21 C22 0.3(6) . . . . yes C19 C20 C21 S1 0.1(9) . . . . yes C11 C20 C21 S1 178.1(4) . . . . yes C1 S1 C21 C22 0.4(4) . . . . yes C1 S1 C21 C20 -177.4(5) . . . . yes C20 C21 C22 C10 178.0(5) . . . . yes S1 C21 C22 C10 -0.1(6) . . . . yes C20 C21 C22 S2 0.1(5) . . . . yes S1 C21 C22 S2 -178.1(3) . . . . yes C9 C10 C22 C21 179.5(5) . . . . yes C1 C10 C22 C21 -0.3(6) . . . . yes C9 C10 C22 S2 -3.2(9) . . . . yes C1 C10 C22 S2 177.1(4) . . . . yes C11 S2 C22 C21 -0.4(4) . . . . yes C11 S2 C22 C10 -177.8(5) . . . . yes _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.492 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.077 # END data_3,10-DMeDNTT _database_code_depnum_ccdc_archive 'CCDC 763569' #TrackingRef '- DMeDNTTs_rev.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,10-DMeDNTT ; _chemical_name_common 3,10-DMeDNTT _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 S2' _chemical_formula_sum 'C24 H16 S2' _chemical_formula_weight 368.49 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' 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/n 1' _symmetry_Int_Tables_number 14 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 6.148(2) _cell_length_b 7.535(3) _cell_length_c 18.559(7) _cell_angle_alpha 90 _cell_angle_beta 97.9240(10) _cell_angle_gamma 90 _cell_volume 851.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2149 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.150 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.317 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.71 _diffrn_standards_number 6211 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1839 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1839 _reflns_number_gt 1469 _reflns_threshold_expression >2sigma(I) _computing_data_collection CRYSTALCLEAR _computing_cell_refinement CRYSTALCLEAR _computing_data_reduction 'teXsan Ver. 1.11' _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^)+(0.0657P)^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 1839 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1146 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _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 S1 S 0.19899(7) -0.12150(6) 0.46100(2) 0.04057(18) Uani 1 1 d . . . C1 C 0.3336(3) -0.0819(2) 0.38542(9) 0.0339(4) Uani 1 1 d . . . C2 C 0.2553(3) -0.12327(19) 0.31444(9) 0.0358(4) Uani 1 1 d . . . C3 C 0.3827(3) -0.0828(2) 0.25953(9) 0.0339(4) Uani 1 1 d . . . C4 C 0.3101(3) -0.1233(2) 0.18518(9) 0.0398(4) Uani 1 1 d . . . C5 C 0.4349(3) -0.0824(2) 0.13263(9) 0.0427(4) Uani 1 1 d . . . C6 C 0.6432(3) 0.0003(2) 0.14903(9) 0.0382(4) Uani 1 1 d . . . C7 C 0.7173(3) 0.0401(2) 0.22029(9) 0.0369(4) Uani 1 1 d . . . C8 C 0.5928(2) 0.00010(19) 0.27731(8) 0.0331(4) Uani 1 1 d . . . C9 C 0.6693(2) 0.0411(2) 0.35066(8) 0.0346(4) Uani 1 1 d . . . C10 C 0.5437(2) 0.00154(19) 0.40443(8) 0.0332(3) Uani 1 1 d . . . C11 C 0.4174(2) -0.0287(2) 0.51819(8) 0.0352(4) Uani 1 1 d . . . C12 C 0.7758(3) 0.0434(3) 0.08918(10) 0.0486(4) Uani 1 1 d . . . H1 H 0.1159 -0.1798 0.3036 0.043 Uiso 1 1 d . . . H2 H 0.1708 -0.1783 0.1722 0.047 Uiso 1 1 d . . . H3 H 0.3843 -0.1127 0.0826 0.051 Uiso 1 1 d . . . H4 H 0.8587 0.0941 0.2321 0.045 Uiso 1 1 d . . . H5 H 0.8090 0.0961 0.3632 0.041 Uiso 1 1 d . . . H6 H 0.9074 0.1034 0.1089 0.058 Uiso 1 1 d . . . H7 H 0.8135 -0.0633 0.0664 0.058 Uiso 1 1 d . . . H8 H 0.6932 0.1174 0.0542 0.058 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 S1 0.0329(3) 0.0501(3) 0.0369(3) -0.00116(17) -0.00168(18) -0.00971(16) C1 0.0304(8) 0.0324(8) 0.0369(8) 0.0015(6) -0.0020(6) -0.0002(6) C2 0.0291(8) 0.0356(9) 0.0404(9) -0.0010(6) -0.0034(7) -0.0037(6) C3 0.0323(8) 0.0310(7) 0.0360(8) -0.0008(6) -0.0036(6) 0.0018(6) C4 0.0359(9) 0.0409(9) 0.0394(9) -0.0042(7) -0.0058(7) -0.0033(6) C5 0.0470(10) 0.0444(9) 0.0342(9) -0.0045(7) -0.0034(7) 0.0022(7) C6 0.0408(9) 0.0350(8) 0.0376(9) -0.0003(6) 0.0008(7) 0.0025(7) C7 0.0342(8) 0.0346(8) 0.0405(9) 0.0011(7) 0.0004(7) 0.0002(6) C8 0.0322(8) 0.0291(8) 0.0360(8) -0.0002(6) -0.0025(6) 0.0000(6) C9 0.0291(8) 0.0341(8) 0.0382(9) 0.0007(6) -0.0038(6) -0.0030(6) C10 0.0309(8) 0.0313(8) 0.0348(8) 0.0009(6) -0.0046(6) -0.0004(6) C11 0.0325(8) 0.0353(8) 0.0355(8) 0.0000(6) -0.0036(6) -0.0021(6) C12 0.0524(11) 0.0534(11) 0.0397(10) 0.0007(8) 0.0057(8) 0.0010(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 C11 1.7392(16) . yes S1 C1 1.7495(18) . yes C1 C2 1.374(2) . yes C1 C10 1.437(2) . yes C2 C3 1.402(2) . yes C3 C4 1.423(2) . yes C3 C8 1.431(2) . yes C4 C5 1.357(2) . yes C5 C6 1.419(2) . yes C6 C7 1.371(2) . yes C6 C12 1.501(2) . yes C7 C8 1.421(2) . yes C8 C9 1.412(2) . yes C9 C10 1.376(2) . yes C10 C11 1.438(2) 3_656 yes C11 C11 1.365(3) 3_656 yes C11 C10 1.438(2) 3_656 yes 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 C11 S1 C1 90.58(8) . . yes C2 C1 C10 121.24(15) . . yes C2 C1 S1 126.02(13) . . yes C10 C1 S1 112.74(12) . . yes C1 C2 C3 119.39(15) . . yes C2 C3 C4 121.74(15) . . yes C2 C3 C8 120.27(14) . . yes C4 C3 C8 117.99(15) . . yes C5 C4 C3 121.01(16) . . yes C4 C5 C6 121.91(15) . . yes C7 C6 C5 118.23(15) . . yes C7 C6 C12 121.61(15) . . yes C5 C6 C12 120.15(15) . . yes C6 C7 C8 122.02(15) . . yes C9 C8 C7 121.97(14) . . yes C9 C8 C3 119.20(14) . . yes C7 C8 C3 118.84(15) . . yes C10 C9 C8 120.41(13) . . yes C9 C10 C1 119.49(14) . . yes C9 C10 C11 131.38(14) . 3_656 yes C1 C10 C11 109.13(14) . 3_656 yes C11 C11 C10 114.59(17) 3_656 3_656 yes C11 C11 S1 112.96(16) 3_656 . yes C10 C11 S1 132.45(12) 3_656 . yes 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 C11 S1 C1 C2 179.97(15) . . . . yes C11 S1 C1 C10 0.03(12) . . . . yes C10 C1 C2 C3 -0.2(2) . . . . yes S1 C1 C2 C3 179.90(11) . . . . yes C1 C2 C3 C4 179.77(14) . . . . yes C1 C2 C3 C8 0.3(2) . . . . yes C2 C3 C4 C5 179.64(15) . . . . yes C8 C3 C4 C5 -0.8(2) . . . . yes C3 C4 C5 C6 0.7(3) . . . . yes C4 C5 C6 C7 -0.5(3) . . . . yes C4 C5 C6 C12 -179.93(16) . . . . yes C5 C6 C7 C8 0.4(2) . . . . yes C12 C6 C7 C8 179.89(14) . . . . yes C6 C7 C8 C9 179.97(14) . . . . yes C6 C7 C8 C3 -0.6(2) . . . . yes C2 C3 C8 C9 -0.2(2) . . . . yes C4 C3 C8 C9 -179.78(14) . . . . yes C2 C3 C8 C7 -179.69(14) . . . . yes C4 C3 C8 C7 0.8(2) . . . . yes C7 C8 C9 C10 179.57(14) . . . . yes C3 C8 C9 C10 0.1(2) . . . . yes C8 C9 C10 C1 -0.1(2) . . . . yes C8 C9 C10 C11 179.98(15) . . . 3_656 yes C2 C1 C10 C9 0.1(2) . . . . yes S1 C1 C10 C9 -179.99(12) . . . . yes C2 C1 C10 C11 -179.96(14) . . . 3_656 yes S1 C1 C10 C11 -0.02(17) . . . 3_656 yes C1 S1 C11 C11 -0.04(17) . . . 3_656 yes C1 S1 C11 C10 180.00(17) . . . 3_656 yes _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.316 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.048 # END