# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'John Wallis' 'Andrew C. Brooks' 'Peter Day' 'Peter Horton' 'Hongchao Li.' 'Louise Male' 'Lee Martin' 'Songjie Yang.' _publ_contact_author_name 'John Wallis' _publ_contact_author_email JOHN.WALLIS@NTU.AC.UK _publ_section_title ; Novel Enantiopure Bis(pyrrolo)tetrathiafulvalene Donors Exhibiting Chiral Crystal Packing Arrangements. ; data_f:\pyrrol~1\sy1\sy1 _database_code_depnum_ccdc_archive 'CCDC 705462' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(S-N-(1-phenylethyl)-2,5-dihdyropyrrolo)tetrathiafulvalene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 N2 S4' _chemical_formula_weight 494.73 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.9951(12) _cell_length_b 6.5877(13) _cell_length_c 15.830(3) _cell_angle_alpha 86.69(3) _cell_angle_beta 83.08(3) _cell_angle_gamma 76.01(3) _cell_volume 602.0(2) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 37149 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour orange _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.412 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12173 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.58 _reflns_number_total 5201 _reflns_number_gt 4924 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _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^)+(0.0750P)^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 constr _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 0.11(6) _chemical_absolute_configuration syn _refine_ls_number_reflns 5201 _refine_ls_number_parameters 291 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1250 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.302 _refine_ls_restrained_S_all 1.301 _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 S1 S -0.89316(9) 0.59672(9) 0.39258(4) 0.01889(16) Uani 1 1 d . . . S2 S -0.78288(9) 0.14100(8) 0.35057(4) 0.01862(17) Uani 1 1 d . . . S21 S -0.47744(9) 0.51278(9) 0.50699(4) 0.01955(17) Uani 1 1 d . . . S22 S -0.35333(9) 0.05435(8) 0.46860(4) 0.01787(17) Uani 1 1 d . . . N1 N -1.2556(4) 0.4917(4) 0.20964(15) 0.0193(5) Uani 1 1 d . . . N21 N 0.0030(4) 0.1893(4) 0.64947(15) 0.0209(5) Uani 1 1 d . . . C1 C -0.7146(5) 0.3421(4) 0.40515(18) 0.0171(5) Uani 1 1 d . . . C2 C -1.0547(5) 0.5162(5) 0.32236(18) 0.0193(5) Uani 1 1 d . . . C3 C -1.0057(5) 0.3129(4) 0.30353(17) 0.0179(5) Uani 1 1 d . . . C4 C -1.2499(5) 0.6400(5) 0.27624(19) 0.0214(6) Uani 1 1 d . . . H4B H -1.3970 0.6723 0.3142 0.026 Uiso 1 1 calc R . . H4A H -1.2165 0.7719 0.2509 0.026 Uiso 1 1 calc R . . C5 C -1.1637(5) 0.2751(5) 0.24274(18) 0.0183(6) Uani 1 1 d . . . H5A H -1.0780 0.1822 0.1967 0.022 Uiso 1 1 calc R . . H5B H -1.2888 0.2144 0.2723 0.022 Uiso 1 1 calc R . . C6 C -1.4815(5) 0.5200(5) 0.17654(18) 0.0233(6) Uani 1 1 d . . . H6 H -1.5931 0.4755 0.2217 0.028 Uiso 1 1 calc R . . C7 C -1.5760(6) 0.7503(5) 0.1514(2) 0.0373(8) Uani 1 1 d . . . H7A H -1.5922 0.8370 0.2010 0.056 Uiso 1 1 calc R . . H7B H -1.7274 0.7673 0.1308 0.056 Uiso 1 1 calc R . . H7C H -1.4688 0.7938 0.1062 0.056 Uiso 1 1 calc R . . C8 C -1.4549(4) 0.3872(4) 0.09933(16) 0.0196(5) Uani 1 1 d . . . C9 C -1.6310(5) 0.2942(5) 0.08442(17) 0.0248(6) Uani 1 1 d . . . H9 H -1.7661 0.3112 0.1240 0.030 Uiso 1 1 calc R . . C10 C -1.6130(5) 0.1770(5) 0.01280(19) 0.0292(6) Uani 1 1 d . . . H10 H -1.7351 0.1148 0.0036 0.035 Uiso 1 1 calc R . . C11 C -1.4168(5) 0.1505(4) -0.04540(18) 0.0279(6) Uani 1 1 d . . . H11 H -1.4028 0.0693 -0.0943 0.034 Uiso 1 1 calc R . . C12 C -1.2403(5) 0.2445(5) -0.03131(17) 0.0282(6) Uani 1 1 d . . . H12 H -1.1056 0.2277 -0.0711 0.034 Uiso 1 1 calc R . . C13 C -1.2593(4) 0.3623(5) 0.04008(17) 0.0251(6) Uani 1 1 d . . . H13 H -1.1382 0.4264 0.0487 0.030 Uiso 1 1 calc R . . C21 C -0.5370(5) 0.3059(4) 0.45419(18) 0.0173(5) Uani 1 1 d . . . C22 C -0.2544(5) 0.3476(4) 0.55553(18) 0.0188(5) Uani 1 1 d . . . C23 C -0.1982(5) 0.1429(4) 0.53949(17) 0.0183(5) Uani 1 1 d . . . C24 C -0.0992(5) 0.3987(5) 0.6143(2) 0.0213(6) Uani 1 1 d . . . H24A H 0.0206 0.4633 0.5830 0.026 Uiso 1 1 calc R . . H24B H -0.1879 0.4931 0.6594 0.026 Uiso 1 1 calc R . . C25 C -0.0002(5) 0.0306(5) 0.58724(17) 0.0185(6) Uani 1 1 d . . . H10B H -0.0300 -0.0992 0.6161 0.022 Uiso 1 1 calc R . . H25A H 0.1466 -0.0039 0.5492 0.022 Uiso 1 1 calc R . . C26 C 0.2283(5) 0.1614(5) 0.68209(18) 0.0224(6) Uani 1 1 d . . . H26 H 0.3532 0.1382 0.6333 0.027 Uiso 1 1 calc R . . C27 C 0.2386(6) 0.3553(5) 0.7296(2) 0.0296(6) Uani 1 1 d . . . H27A H 0.2248 0.4762 0.6898 0.044 Uiso 1 1 calc R . . H27B H 0.3864 0.3298 0.7536 0.044 Uiso 1 1 calc R . . H27C H 0.1113 0.3835 0.7755 0.044 Uiso 1 1 calc R . . C28 C 0.2715(4) -0.0247(4) 0.74373(17) 0.0198(5) Uani 1 1 d . . . C29 C 0.4968(5) -0.1397(5) 0.75243(18) 0.0262(6) Uani 1 1 d . . . H29 H 0.6209 -0.1150 0.7131 0.031 Uiso 1 1 calc R . . C30 C 0.5422(5) -0.2888(5) 0.81724(19) 0.0290(6) Uani 1 1 d . . . H30 H 0.6963 -0.3660 0.8220 0.035 Uiso 1 1 calc R . . C31 C 0.3618(5) -0.3257(5) 0.87566(19) 0.0291(6) Uani 1 1 d . . . H31 H 0.3929 -0.4239 0.9216 0.035 Uiso 1 1 calc R . . C32 C 0.1361(5) -0.2177(5) 0.86614(18) 0.0266(6) Uani 1 1 d . . . H32 H 0.0118 -0.2456 0.9046 0.032 Uiso 1 1 calc R . . C33 C 0.0917(4) -0.0690(4) 0.80053(17) 0.0222(5) Uani 1 1 d . . . H33 H -0.0633 0.0034 0.7943 0.027 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 0.0192(3) 0.0167(3) 0.0207(3) -0.0023(3) -0.0030(3) -0.0031(3) S2 0.0180(3) 0.0157(3) 0.0219(3) -0.0018(3) -0.0032(3) -0.0027(3) S21 0.0187(3) 0.0164(4) 0.0239(4) -0.0025(3) -0.0033(3) -0.0039(3) S22 0.0163(3) 0.0167(3) 0.0206(3) -0.0029(3) -0.0024(3) -0.0030(3) N1 0.0209(11) 0.0176(11) 0.0178(11) -0.0001(8) -0.0041(9) -0.0003(9) N21 0.0210(11) 0.0214(11) 0.0223(12) -0.0020(9) -0.0060(9) -0.0067(9) C1 0.0146(12) 0.0171(12) 0.0186(13) -0.0014(10) 0.0016(10) -0.0032(10) C2 0.0180(13) 0.0199(13) 0.0186(14) 0.0000(11) -0.0010(10) -0.0027(11) C3 0.0158(12) 0.0184(13) 0.0188(13) 0.0012(10) -0.0015(10) -0.0032(10) C4 0.0213(14) 0.0216(14) 0.0212(14) -0.0015(11) -0.0055(11) -0.0034(11) C5 0.0166(13) 0.0197(14) 0.0176(13) -0.0004(11) -0.0010(10) -0.0027(11) C6 0.0192(14) 0.0298(16) 0.0181(13) -0.0030(11) -0.0028(10) 0.0002(11) C7 0.0400(18) 0.0317(17) 0.0338(17) -0.0075(13) -0.0191(14) 0.0127(13) C8 0.0179(12) 0.0214(13) 0.0171(12) 0.0018(10) -0.0031(9) -0.0001(10) C9 0.0217(13) 0.0320(15) 0.0217(13) 0.0029(11) -0.0021(10) -0.0095(11) C10 0.0299(15) 0.0297(15) 0.0309(15) 0.0002(12) -0.0089(12) -0.0104(12) C11 0.0334(15) 0.0242(14) 0.0242(13) -0.0042(11) -0.0063(11) -0.0004(11) C12 0.0236(13) 0.0367(16) 0.0196(13) -0.0053(11) 0.0008(10) 0.0013(12) C13 0.0183(12) 0.0327(15) 0.0239(13) -0.0017(11) -0.0035(10) -0.0042(11) C21 0.0155(12) 0.0194(13) 0.0171(13) -0.0027(10) -0.0005(10) -0.0045(10) C22 0.0185(13) 0.0195(13) 0.0188(13) -0.0011(10) -0.0010(10) -0.0057(11) C23 0.0164(13) 0.0215(13) 0.0177(13) -0.0011(11) -0.0008(10) -0.0063(11) C24 0.0232(15) 0.0214(15) 0.0199(14) -0.0021(11) -0.0018(11) -0.0063(12) C25 0.0187(14) 0.0197(14) 0.0175(13) -0.0017(11) -0.0024(11) -0.0051(11) C26 0.0190(14) 0.0314(16) 0.0191(13) -0.0002(12) -0.0032(11) -0.0103(12) C27 0.0355(16) 0.0287(15) 0.0295(15) -0.0008(12) -0.0116(12) -0.0132(12) C28 0.0195(12) 0.0239(14) 0.0171(11) -0.0052(10) -0.0010(9) -0.0068(10) C29 0.0202(13) 0.0333(15) 0.0245(13) -0.0060(11) -0.0021(10) -0.0042(11) C30 0.0243(14) 0.0275(15) 0.0341(15) -0.0062(12) -0.0077(11) -0.0005(11) C31 0.0374(16) 0.0233(14) 0.0270(14) -0.0008(11) -0.0096(12) -0.0053(12) C32 0.0281(14) 0.0276(14) 0.0235(13) -0.0002(11) -0.0008(11) -0.0068(11) C33 0.0182(12) 0.0254(14) 0.0213(12) -0.0022(10) -0.0005(9) -0.0021(10) _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 C2 1.741(3) . ? S1 C1 1.773(3) . ? S2 C3 1.741(3) . ? S2 C1 1.775(3) . ? S21 C22 1.735(3) . ? S21 C21 1.767(3) . ? S22 C23 1.748(3) . ? S22 C21 1.773(3) . ? N1 C6 1.477(4) . ? N1 C4 1.487(4) . ? N1 C5 1.489(4) . ? N21 C26 1.471(3) . ? N21 C24 1.474(4) . ? N21 C25 1.482(4) . ? C1 C21 1.360(3) . ? C2 C3 1.343(4) . ? C2 C4 1.498(4) . ? C3 C5 1.499(4) . ? C6 C8 1.514(4) . ? C6 C7 1.533(4) . ? C8 C9 1.391(4) . ? C8 C13 1.394(4) . ? C9 C10 1.387(4) . ? C10 C11 1.386(4) . ? C11 C12 1.394(4) . ? C12 C13 1.385(4) . ? C22 C23 1.340(4) . ? C22 C24 1.496(4) . ? C23 C25 1.501(4) . ? C26 C28 1.514(4) . ? C26 C27 1.536(4) . ? C28 C33 1.394(4) . ? C28 C29 1.398(4) . ? C29 C30 1.383(4) . ? C30 C31 1.394(4) . ? C31 C32 1.390(4) . ? C32 C33 1.390(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 C2 S1 C1 93.31(14) . . ? C3 S2 C1 93.38(14) . . ? C22 S21 C21 92.97(14) . . ? C23 S22 C21 93.16(14) . . ? C6 N1 C4 115.0(2) . . ? C6 N1 C5 113.2(2) . . ? C4 N1 C5 108.1(2) . . ? C26 N21 C24 116.7(2) . . ? C26 N21 C25 113.4(2) . . ? C24 N21 C25 108.8(2) . . ? C21 C1 S1 121.22(18) . . ? C21 C1 S2 122.73(18) . . ? S1 C1 S2 116.05(16) . . ? C3 C2 C4 111.1(3) . . ? C3 C2 S1 118.7(2) . . ? C4 C2 S1 130.2(2) . . ? C2 C3 C5 110.6(2) . . ? C2 C3 S2 118.5(2) . . ? C5 C3 S2 130.9(2) . . ? N1 C4 C2 101.0(2) . . ? N1 C5 C3 101.1(2) . . ? N1 C6 C8 109.8(2) . . ? N1 C6 C7 110.3(3) . . ? C8 C6 C7 109.2(2) . . ? C9 C8 C13 118.6(2) . . ? C9 C8 C6 120.3(2) . . ? C13 C8 C6 121.1(2) . . ? C10 C9 C8 121.2(3) . . ? C11 C10 C9 120.0(3) . . ? C10 C11 C12 119.2(3) . . ? C13 C12 C11 120.7(3) . . ? C12 C13 C8 120.4(3) . . ? C1 C21 S21 120.63(18) . . ? C1 C21 S22 122.90(18) . . ? S21 C21 S22 116.47(16) . . ? C23 C22 C24 111.0(3) . . ? C23 C22 S21 119.5(2) . . ? C24 C22 S21 129.4(2) . . ? C22 C23 C25 110.5(2) . . ? C22 C23 S22 117.8(2) . . ? C25 C23 S22 131.7(2) . . ? N21 C24 C22 101.3(2) . . ? N21 C25 C23 101.3(2) . . ? N21 C26 C28 110.9(2) . . ? N21 C26 C27 110.9(2) . . ? C28 C26 C27 107.7(2) . . ? C33 C28 C29 118.2(2) . . ? C33 C28 C26 120.7(2) . . ? C29 C28 C26 120.5(2) . . ? C30 C29 C28 121.2(3) . . ? C29 C30 C31 120.0(3) . . ? C32 C31 C30 119.5(3) . . ? C31 C32 C33 120.2(3) . . ? C32 C33 C28 120.9(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.122 _refine_diff_density_min -1.157 _refine_diff_density_rms 0.378 #===END data_f:\pyrrol~1\tetrag\tetragl _database_code_depnum_ccdc_archive 'CCDC 705463' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(S-N-(1-phenylethyl)pyrrolo)tetrathiafulvalene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 N2 S4' _chemical_formula_weight 490.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P43212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+3/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+1/4' 'x+1/2, -y+1/2, -z+1/4' '-x+1/2, y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 7.4847(4) _cell_length_b 7.4847(4) _cell_length_c 42.565(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2384.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 16426 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.416 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12539 _diffrn_reflns_av_R_equivalents 0.0966 _diffrn_reflns_av_sigmaI/netI 0.1141 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 55 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.57 _reflns_number_total 2670 _reflns_number_gt 1765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _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^)+(0.0000P)^2^+6.5855P] 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 constr _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 0.0(3) _chemical_absolute_configuration syn _refine_ls_number_reflns 2670 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1479 _refine_ls_R_factor_gt 0.0893 _refine_ls_wR_factor_ref 0.1486 _refine_ls_wR_factor_gt 0.1303 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _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 S2 S 0.8538(2) 0.1437(2) 0.01231(3) 0.0272(3) Uani 1 1 d . . . S1 S 1.1440(2) 0.4232(2) 0.01324(3) 0.0288(3) Uani 1 1 d . . . C1 C 1.0811(7) 0.1985(7) 0.00556(11) 0.0250(12) Uani 1 1 d . . . N1 N 0.7087(6) 0.5806(6) 0.05758(9) 0.0260(10) Uani 1 1 d . . . C4 C 0.8808(8) 0.6198(8) 0.04843(12) 0.0270(13) Uani 1 1 d . . . H4 H 0.9447 0.7266 0.0528 0.032 Uiso 1 1 calc R . . C3 C 0.8046(7) 0.3470(8) 0.03101(11) 0.0219(12) Uani 1 1 d . . . C5 C 0.6607(8) 0.4162(7) 0.04655(12) 0.0266(13) Uani 1 1 d . . . H5 H 0.5478 0.3601 0.0492 0.032 Uiso 1 1 calc R . . C2 C 0.9418(8) 0.4765(7) 0.03196(13) 0.0248(13) Uani 1 1 d . . . C6 C 0.5949(8) 0.7071(8) 0.07579(11) 0.0287(13) Uani 1 1 d . . . H6 H 0.6761 0.7882 0.0878 0.034 Uiso 1 1 calc R . . C8 C 0.4863(9) 0.6003(8) 0.09945(13) 0.0320(15) Uani 1 1 d . . . C9 C 0.3102(9) 0.5534(8) 0.09400(15) 0.0417(18) Uani 1 1 d . . . H9 H 0.2515 0.5918 0.0754 0.050 Uiso 1 1 calc R . . C13 C 0.5678(11) 0.5460(9) 0.12705(15) 0.0497(19) Uani 1 1 d . . . H13 H 0.6883 0.5788 0.1310 0.060 Uiso 1 1 calc R . . C11 C 0.3029(17) 0.3948(10) 0.1431(2) 0.084(4) Uani 1 1 d . . . H11 H 0.2403 0.3226 0.1577 0.101 Uiso 1 1 calc R . . C12 C 0.4763(15) 0.4447(12) 0.14887(17) 0.074(3) Uani 1 1 d . . . H12 H 0.5331 0.4096 0.1679 0.089 Uiso 1 1 calc R . . C10 C 0.2203(11) 0.4502(10) 0.1158(2) 0.070(3) Uani 1 1 d . . . H10 H 0.0998 0.4169 0.1120 0.084 Uiso 1 1 calc R . . C7 C 0.4867(9) 0.8206(9) 0.05367(13) 0.0467(18) Uani 1 1 d . . . H7A H 0.5672 0.8905 0.0403 0.070 Uiso 1 1 calc R . . H7B H 0.4104 0.9015 0.0658 0.070 Uiso 1 1 calc R . . H7C H 0.4120 0.7435 0.0405 0.070 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 S2 0.0224(8) 0.0239(8) 0.0354(6) -0.0059(7) 0.0038(7) -0.0027(6) S1 0.0228(8) 0.0232(8) 0.0405(7) -0.0064(8) 0.0048(8) -0.0029(7) C1 0.027(3) 0.025(3) 0.023(3) -0.001(2) -0.003(2) -0.001(2) N1 0.024(3) 0.021(3) 0.032(2) -0.007(2) 0.004(2) 0.000(2) C4 0.028(4) 0.021(3) 0.033(3) 0.002(3) -0.005(3) -0.007(3) C3 0.022(3) 0.021(3) 0.023(3) -0.005(3) -0.001(2) 0.001(3) C5 0.022(3) 0.023(3) 0.034(3) -0.003(2) -0.003(3) 0.004(3) C2 0.023(3) 0.017(3) 0.034(3) -0.002(3) 0.001(3) -0.006(3) C6 0.032(4) 0.025(3) 0.029(3) 0.001(3) 0.010(3) 0.002(3) C8 0.046(4) 0.024(4) 0.026(3) -0.006(3) 0.010(3) 0.002(3) C9 0.050(5) 0.034(4) 0.042(3) -0.010(3) 0.012(3) -0.012(3) C13 0.071(5) 0.043(5) 0.035(3) -0.011(4) 0.001(4) 0.022(4) C11 0.165(11) 0.017(5) 0.070(6) 0.004(4) 0.074(7) 0.009(5) C12 0.138(10) 0.060(6) 0.025(4) 0.012(4) 0.022(5) 0.041(6) C10 0.085(7) 0.034(5) 0.090(6) -0.023(5) 0.051(5) -0.017(4) C7 0.049(5) 0.046(5) 0.045(3) 0.019(3) 0.018(3) 0.019(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 S2 C3 1.756(5) . ? S2 C1 1.773(6) . ? S1 C2 1.756(6) . ? S1 C1 1.777(6) . ? C1 C1 1.329(10) 7_645 ? N1 C5 1.365(7) . ? N1 C4 1.377(7) . ? N1 C6 1.491(6) . ? C4 C2 1.360(8) . ? C3 C5 1.366(7) . ? C3 C2 1.413(7) . ? C6 C7 1.504(7) . ? C6 C8 1.521(8) . ? C8 C9 1.383(9) . ? C8 C13 1.385(9) . ? C9 C10 1.383(9) . ? C13 C12 1.381(10) . ? C11 C12 1.373(13) . ? C11 C10 1.378(12) . ? 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 C3 S2 C1 94.3(3) . . ? C2 S1 C1 94.0(3) . . ? C1 C1 S2 122.61(18) 7_645 . ? C1 C1 S1 121.06(18) 7_645 . ? S2 C1 S1 116.3(3) . . ? C5 N1 C4 109.9(4) . . ? C5 N1 C6 126.9(5) . . ? C4 N1 C6 123.1(5) . . ? C2 C4 N1 107.0(5) . . ? C5 C3 C2 107.4(5) . . ? C5 C3 S2 135.5(5) . . ? C2 C3 S2 117.1(4) . . ? N1 C5 C3 107.5(5) . . ? C4 C2 C3 108.2(5) . . ? C4 C2 S1 134.6(4) . . ? C3 C2 S1 117.2(4) . . ? N1 C6 C7 109.9(4) . . ? N1 C6 C8 108.4(5) . . ? C7 C6 C8 115.0(5) . . ? C9 C8 C13 119.2(6) . . ? C9 C8 C6 122.1(6) . . ? C13 C8 C6 118.7(6) . . ? C10 C9 C8 119.5(7) . . ? C12 C13 C8 120.9(8) . . ? C12 C11 C10 119.6(8) . . ? C11 C12 C13 119.8(8) . . ? C11 C10 C9 121.0(8) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.438 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.089 #===END data_f:\pyrrol~1\nap\nap _database_code_depnum_ccdc_archive 'CCDC 705464' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(R-N-(1-naphthyl)ethyl-2,5-dihydropyrrolo)tetrathiafulvalene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H30 N2 S4' _chemical_formula_weight 594.84 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' 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.705(3) _cell_length_b 6.1713(12) _cell_length_c 19.492(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.72(3) _cell_angle_gamma 90.00 _cell_volume 1447.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 54885 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.356 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 4096x4096pixels/62x62mm _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19829 _diffrn_reflns_av_R_equivalents 0.0785 _diffrn_reflns_av_sigmaI/netI 0.0961 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 28.06 _reflns_number_total 6504 _reflns_number_gt 4594 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _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^)+(0.0000P)^2^+3.6159P] 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 constr _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 -0.11(16) _chemical_absolute_configuration syn _refine_ls_number_reflns 6504 _refine_ls_number_parameters 363 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1236 _refine_ls_R_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.1555 _refine_ls_wR_factor_gt 0.1344 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 S1 S 0.88004(11) 0.0180(3) 0.06302(8) 0.0324(4) Uani 1 1 d . . . S2 S 0.63582(11) -0.0185(3) 0.04044(8) 0.0346(4) Uani 1 1 d . . . S21 S 0.86622(11) -0.4157(3) -0.03440(8) 0.0334(4) Uani 1 1 d . . . S22 S 0.62185(11) -0.4433(3) -0.05628(8) 0.0343(4) Uani 1 1 d . . . N1 N 0.7750(4) 0.4829(10) 0.1729(2) 0.0345(13) Uani 1 1 d . . . N21 N 0.7124(4) -0.8540(10) -0.1860(3) 0.0375(14) Uani 1 1 d . . . C1 C 0.7551(4) -0.1304(12) 0.0233(3) 0.0289(14) Uani 1 1 d . . . C2 C 0.8190(4) 0.2068(12) 0.1051(3) 0.0310(15) Uani 1 1 d . . . C3 C 0.7102(5) 0.1895(13) 0.0946(3) 0.0329(15) Uani 1 1 d . . . C4 C 0.8702(5) 0.3830(13) 0.1566(3) 0.0351(15) Uani 1 1 d . . . H4A H 0.9251 0.3245 0.2011 0.042 Uiso 1 1 calc R . . H4B H 0.9076 0.4895 0.1343 0.042 Uiso 1 1 calc R . . C5 C 0.6724(5) 0.3542(13) 0.1372(3) 0.0390(17) Uani 1 1 d . . . H5A H 0.6442 0.2844 0.1736 0.047 Uiso 1 1 calc R . . H5B H 0.6132 0.4468 0.1052 0.047 Uiso 1 1 calc R . . C6 C 0.7943(4) 0.5176(10) 0.2498(3) 0.0320(12) Uani 1 1 d . . . H6 H 0.7944 0.3735 0.2733 0.038 Uiso 1 1 calc R . . C7 C 0.7008(5) 0.6560(13) 0.2611(3) 0.0426(17) Uani 1 1 d . . . H7A H 0.6940 0.7913 0.2337 0.064 Uiso 1 1 calc R . . H7B H 0.7182 0.6891 0.3127 0.064 Uiso 1 1 calc R . . H7C H 0.6306 0.5760 0.2440 0.064 Uiso 1 1 calc R . . C8 C 0.9056(5) 0.6264(11) 0.2861(3) 0.0350(16) Uani 1 1 d . . . C9 C 0.9307(5) 0.8063(12) 0.2525(4) 0.0415(17) Uani 1 1 d . . . H9 H 0.8790 0.8552 0.2083 0.050 Uiso 1 1 calc R . . C10 C 1.0318(6) 0.9198(13) 0.2826(4) 0.0499(18) Uani 1 1 d . . . H10 H 1.0477 1.0428 0.2583 0.060 Uiso 1 1 calc R . . C11 C 1.1054(5) 0.8535(13) 0.3456(4) 0.048(2) Uani 1 1 d . . . H11 H 1.1729 0.9314 0.3651 0.057 Uiso 1 1 calc R . . C12 C 1.0854(5) 0.6729(12) 0.3832(3) 0.0378(16) Uani 1 1 d . . . C13 C 1.1639(5) 0.6017(14) 0.4470(4) 0.058(2) Uani 1 1 d . . . H13 H 1.2324 0.6768 0.4660 0.070 Uiso 1 1 calc R . . C14 C 1.1426(5) 0.4228(15) 0.4828(4) 0.062(2) Uani 1 1 d . . . H14 H 1.1973 0.3753 0.5259 0.075 Uiso 1 1 calc R . . C15 C 1.0425(6) 0.3096(15) 0.4571(4) 0.056(2) Uani 1 1 d . . . H15 H 1.0281 0.1902 0.4835 0.067 Uiso 1 1 calc R . . C16 C 0.9636(5) 0.3740(12) 0.3920(3) 0.0425(15) Uani 1 1 d . . . H16 H 0.8965 0.2942 0.3736 0.051 Uiso 1 1 calc R . . C17 C 0.9820(5) 0.5565(13) 0.3530(3) 0.0354(15) Uani 1 1 d . . . C21 C 0.7488(4) -0.3062(12) -0.0168(3) 0.0309(15) Uani 1 1 d . . . C22 C 0.7882(5) -0.6147(12) -0.0935(3) 0.0301(14) Uani 1 1 d . . . C23 C 0.6796(5) -0.6253(11) -0.1022(3) 0.0298(14) Uani 1 1 d . . . C24 C 0.8221(5) -0.7909(12) -0.1349(3) 0.0322(15) Uani 1 1 d . . . H24A H 0.8723 -0.7360 -0.1607 0.039 Uiso 1 1 calc R . . H24B H 0.8583 -0.9128 -0.1031 0.039 Uiso 1 1 calc R . . C25 C 0.6262(5) -0.8030(13) -0.1526(3) 0.0365(16) Uani 1 1 d . . . H25A H 0.6102 -0.9293 -0.1262 0.044 Uiso 1 1 calc R . . H26B H 0.5565 -0.7539 -0.1892 0.044 Uiso 1 1 calc R . . C26 C 0.7034(5) -1.0741(11) -0.2149(3) 0.0397(15) Uani 1 1 d . . . H26 H 0.7091 -1.1765 -0.1741 0.048 Uiso 1 1 calc R . . C27 C 0.7992(5) -1.1254(15) -0.2444(4) 0.055(2) Uani 1 1 d . . . H27A H 0.8026 -1.0140 -0.2795 0.082 Uiso 1 1 calc R . . H27B H 0.7867 -1.2673 -0.2683 0.082 Uiso 1 1 calc R . . H27C H 0.8695 -1.1277 -0.2044 0.082 Uiso 1 1 calc R . . C28 C 0.5893(5) -1.1112(12) -0.2734(3) 0.0382(16) Uani 1 1 d . . . C29 C 0.5268(6) -1.2875(12) -0.2664(4) 0.0454(17) Uani 1 1 d . . . H29 H 0.5556 -1.3794 -0.2256 0.055 Uiso 1 1 calc R . . C30 C 0.4242(6) -1.3375(14) -0.3159(4) 0.0495(18) Uani 1 1 d . . . H30 H 0.3849 -1.4623 -0.3092 0.059 Uiso 1 1 calc R . . C31 C 0.3798(6) -1.2058(13) -0.3746(4) 0.052(2) Uani 1 1 d . . . H31 H 0.3087 -1.2374 -0.4081 0.062 Uiso 1 1 calc R . . C32 C 0.4399(5) -1.0218(12) -0.3855(3) 0.0372(16) Uani 1 1 d . . . C33 C 0.3970(5) -0.8882(11) -0.4450(4) 0.0454(16) Uani 1 1 d . . . H33 H 0.3264 -0.9211 -0.4790 0.055 Uiso 1 1 calc R . . C34 C 0.4530(6) -0.7118(15) -0.4561(4) 0.055(2) Uani 1 1 d . . . H34 H 0.4222 -0.6227 -0.4974 0.065 Uiso 1 1 calc R . . C35 C 0.5563(5) -0.6625(12) -0.4061(3) 0.0476(17) Uani 1 1 d . . . H35 H 0.5949 -0.5384 -0.4142 0.057 Uiso 1 1 calc R . . C36 C 0.6038(5) -0.7840(11) -0.3465(3) 0.0409(15) Uani 1 1 d . . . H36 H 0.6740 -0.7450 -0.3133 0.049 Uiso 1 1 calc R . . C37 C 0.5459(5) -0.9749(13) -0.3339(3) 0.0351(15) 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 S1 0.0179(6) 0.0445(11) 0.0366(8) -0.0032(8) 0.0111(6) -0.0021(7) S2 0.0179(7) 0.0429(11) 0.0440(9) -0.0091(8) 0.0114(6) -0.0017(7) S21 0.0186(7) 0.0419(11) 0.0419(9) -0.0010(8) 0.0128(6) 0.0022(7) S22 0.0206(7) 0.0382(10) 0.0468(9) -0.0108(8) 0.0144(6) -0.0016(8) N1 0.023(2) 0.049(4) 0.031(3) -0.008(3) 0.0077(19) 0.002(2) N21 0.028(2) 0.047(4) 0.038(3) -0.004(3) 0.011(2) 0.003(2) C1 0.015(3) 0.035(4) 0.035(3) 0.002(3) 0.007(2) -0.005(3) C2 0.015(3) 0.045(4) 0.033(3) 0.002(3) 0.009(2) -0.005(3) C3 0.026(3) 0.041(4) 0.027(3) 0.003(3) 0.002(2) 0.003(3) C4 0.026(3) 0.041(4) 0.038(3) -0.003(3) 0.010(3) 0.006(3) C5 0.023(3) 0.055(5) 0.036(4) -0.009(4) 0.005(3) -0.002(3) C6 0.027(3) 0.034(3) 0.035(3) -0.003(3) 0.008(2) -0.006(2) C7 0.036(3) 0.052(4) 0.042(4) -0.014(3) 0.016(3) -0.006(3) C8 0.030(3) 0.043(4) 0.035(3) -0.009(3) 0.015(3) -0.002(3) C9 0.037(3) 0.048(5) 0.039(4) 0.001(3) 0.012(3) 0.002(3) C10 0.047(4) 0.046(5) 0.062(5) -0.003(4) 0.024(4) -0.004(4) C11 0.033(3) 0.057(6) 0.053(4) -0.024(4) 0.012(3) -0.016(4) C12 0.036(3) 0.050(5) 0.026(3) -0.013(3) 0.008(3) 0.008(3) C13 0.034(3) 0.090(7) 0.047(4) -0.017(4) 0.008(3) -0.006(4) C14 0.035(4) 0.094(7) 0.052(5) 0.015(5) 0.006(3) 0.014(4) C15 0.066(5) 0.067(6) 0.038(4) 0.010(4) 0.023(4) 0.006(5) C16 0.047(4) 0.042(4) 0.041(4) 0.005(3) 0.017(3) 0.001(3) C17 0.035(3) 0.040(4) 0.031(3) -0.008(3) 0.011(2) 0.008(3) C21 0.016(3) 0.039(4) 0.037(3) -0.003(3) 0.008(2) 0.001(3) C22 0.024(3) 0.033(4) 0.033(3) 0.001(3) 0.009(2) 0.002(3) C23 0.028(3) 0.028(3) 0.034(3) -0.004(3) 0.011(3) 0.010(3) C24 0.028(3) 0.036(4) 0.036(3) 0.004(3) 0.014(3) 0.012(3) C25 0.027(3) 0.044(4) 0.042(4) 0.000(4) 0.017(3) 0.006(3) C26 0.036(3) 0.046(4) 0.038(4) -0.007(3) 0.013(3) 0.009(3) C27 0.040(4) 0.075(6) 0.045(4) -0.015(4) 0.009(3) 0.019(4) C28 0.046(4) 0.039(4) 0.032(3) -0.002(3) 0.016(3) 0.008(3) C29 0.054(4) 0.036(4) 0.047(4) 0.004(3) 0.018(4) 0.000(4) C30 0.060(4) 0.050(5) 0.043(4) -0.003(4) 0.022(3) -0.013(4) C31 0.052(4) 0.055(5) 0.056(5) -0.009(4) 0.027(4) -0.003(4) C32 0.037(3) 0.045(4) 0.030(3) -0.009(3) 0.012(3) 0.006(3) C33 0.051(4) 0.047(4) 0.040(4) -0.004(3) 0.017(3) 0.006(3) C34 0.054(4) 0.068(6) 0.041(4) 0.006(4) 0.015(3) 0.010(5) C35 0.047(4) 0.057(5) 0.042(4) 0.003(4) 0.019(3) 0.002(4) C36 0.038(3) 0.050(4) 0.039(4) -0.003(3) 0.019(3) 0.003(3) C37 0.034(3) 0.044(4) 0.035(3) -0.007(3) 0.021(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 C2 1.743(7) . ? S1 C1 1.780(6) . ? S2 C3 1.736(7) . ? S2 C1 1.792(6) . ? S21 C22 1.756(7) . ? S21 C21 1.769(6) . ? S22 C23 1.739(6) . ? S22 C21 1.764(6) . ? N1 C6 1.454(7) . ? N1 C4 1.480(7) . ? N1 C5 1.495(8) . ? N21 C26 1.461(8) . ? N21 C25 1.477(7) . ? N21 C24 1.481(7) . ? C1 C21 1.325(6) . ? C2 C3 1.336(7) . ? C2 C4 1.481(9) . ? C3 C5 1.486(9) . ? C6 C8 1.519(8) . ? C6 C7 1.535(8) . ? C8 C9 1.377(9) . ? C8 C17 1.420(8) . ? C9 C10 1.414(9) . ? C10 C11 1.347(9) . ? C11 C12 1.401(10) . ? C12 C13 1.393(9) . ? C12 C17 1.446(9) . ? C13 C14 1.378(11) . ? C14 C15 1.395(11) . ? C15 C16 1.398(9) . ? C16 C17 1.420(9) . ? C22 C23 1.336(8) . ? C22 C24 1.499(9) . ? C23 C25 1.483(10) . ? C26 C27 1.538(8) . ? C26 C28 1.547(8) . ? C28 C29 1.379(10) . ? C28 C37 1.409(9) . ? C29 C30 1.384(9) . ? C30 C31 1.368(10) . ? C31 C32 1.422(9) . ? C32 C33 1.384(9) . ? C32 C37 1.428(8) . ? C33 C34 1.355(11) . ? C34 C35 1.395(10) . ? C35 C36 1.351(9) . ? C36 C37 1.451(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 C2 S1 C1 94.6(3) . . ? C3 S2 C1 94.0(3) . . ? C22 S21 C21 93.4(3) . . ? C23 S22 C21 93.2(3) . . ? C6 N1 C4 113.8(4) . . ? C6 N1 C5 113.1(5) . . ? C4 N1 C5 109.2(5) . . ? C26 N21 C25 113.0(5) . . ? C26 N21 C24 116.4(5) . . ? C25 N21 C24 108.6(5) . . ? C21 C1 S1 123.7(4) . . ? C21 C1 S2 122.0(4) . . ? S1 C1 S2 114.2(4) . . ? C3 C2 C4 111.8(6) . . ? C3 C2 S1 118.0(5) . . ? C4 C2 S1 130.1(4) . . ? C2 C3 C5 111.3(6) . . ? C2 C3 S2 119.2(5) . . ? C5 C3 S2 129.4(4) . . ? N1 C4 C2 103.9(5) . . ? C3 C5 N1 103.5(5) . . ? N1 C6 C8 111.7(4) . . ? N1 C6 C7 110.3(4) . . ? C8 C6 C7 109.5(5) . . ? C9 C8 C17 119.1(6) . . ? C9 C8 C6 117.2(6) . . ? C17 C8 C6 123.6(6) . . ? C8 C9 C10 121.4(6) . . ? C11 C10 C9 120.0(7) . . ? C10 C11 C12 121.9(6) . . ? C13 C12 C11 121.3(7) . . ? C13 C12 C17 120.2(7) . . ? C11 C12 C17 118.4(6) . . ? C14 C13 C12 120.2(7) . . ? C13 C14 C15 121.6(7) . . ? C14 C15 C16 119.2(8) . . ? C15 C16 C17 121.3(6) . . ? C8 C17 C16 123.5(6) . . ? C8 C17 C12 119.2(6) . . ? C16 C17 C12 117.4(6) . . ? C1 C21 S22 121.6(3) . . ? C1 C21 S21 122.1(4) . . ? S22 C21 S21 116.3(4) . . ? C23 C22 C24 111.0(6) . . ? C23 C22 S21 117.4(5) . . ? C24 C22 S21 131.4(4) . . ? C22 C23 C25 110.8(5) . . ? C22 C23 S22 119.4(5) . . ? C25 C23 S22 129.8(4) . . ? N21 C24 C22 100.5(4) . . ? N21 C25 C23 101.7(5) . . ? N21 C26 C27 111.2(6) . . ? N21 C26 C28 111.2(5) . . ? C27 C26 C28 111.2(5) . . ? C29 C28 C37 118.0(6) . . ? C29 C28 C26 118.5(6) . . ? C37 C28 C26 123.4(6) . . ? C28 C29 C30 123.4(7) . . ? C31 C30 C29 119.5(8) . . ? C30 C31 C32 120.2(7) . . ? C33 C32 C31 121.0(6) . . ? C33 C32 C37 119.9(6) . . ? C31 C32 C37 119.1(6) . . ? C34 C33 C32 121.8(7) . . ? C33 C34 C35 119.2(7) . . ? C36 C35 C34 122.7(7) . . ? C35 C36 C37 119.0(6) . . ? C28 C37 C32 119.7(6) . . ? C28 C37 C36 122.9(6) . . ? C32 C37 C36 117.4(6) . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.422 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.087 #===END data_f:\pyrrol~1\soln6\soln6 _database_code_depnum_ccdc_archive 'CCDC 705465' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(R-N-(1-naphthyl)ethylpyrrolo)tetrathiafulvalene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H26 N2 S4' _chemical_formula_weight 590.3 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M C2221 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, -z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z+1/2' _cell_length_a 10.8652(2) _cell_length_b 10.8969(2) _cell_length_c 47.0032(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5565.04(19) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 52065 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description slab _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 0.370 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46634 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -61 _diffrn_reflns_limit_l_max 60 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6318 _reflns_number_gt 5904 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _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^)+(0.0447P)^2^+25.5188P] 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 constr _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 0.10(11) _chemical_absolute_configuration syn _refine_ls_number_reflns 6318 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1558 _refine_ls_wR_factor_gt 0.1539 _refine_ls_goodness_of_fit_ref 1.208 _refine_ls_restrained_S_all 1.208 _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 -0.22380(9) 1.36601(11) 0.98775(2) 0.0279(2) Uani 1 1 d . . . S2 S 0.05426(10) 1.36052(11) 0.98724(2) 0.0286(2) Uani 1 1 d . . . N1 N -0.0923(4) 1.0774(3) 0.94750(7) 0.0261(7) Uani 1 1 d . . . C1 C -0.0818(4) 1.4423(4) 0.99472(8) 0.0263(9) Uani 1 1 d . . . C2 C -0.1542(4) 1.2423(4) 0.97055(9) 0.0254(9) Uani 1 1 d . . . C3 C -0.0238(4) 1.2396(4) 0.97035(8) 0.0249(9) Uani 1 1 d . . . C4 C -0.1946(4) 1.1398(5) 0.95653(8) 0.0290(9) Uani 1 1 d . . . H4 H -0.2778 1.1164 0.9536 0.035 Uiso 1 1 calc R . . C5 C 0.0126(4) 1.1365(4) 0.95601(8) 0.0240(8) Uani 1 1 d . . . H5 H 0.0949 1.1109 0.9526 0.029 Uiso 1 1 calc R . . C6 C -0.0972(5) 0.9493(4) 0.93640(9) 0.0275(9) Uani 1 1 d . . . H6 H -0.1795 0.9374 0.9273 0.033 Uiso 1 1 calc R . . C7 C -0.0892(6) 0.8611(5) 0.96172(10) 0.0398(11) Uani 1 1 d . . . H7A H -0.1489 0.8857 0.9763 0.060 Uiso 1 1 calc R . . H7B H -0.0060 0.8638 0.9697 0.060 Uiso 1 1 calc R . . H7C H -0.1075 0.7775 0.9553 0.060 Uiso 1 1 calc R . . C8 C 0.0002(4) 0.9310(4) 0.91354(9) 0.0263(9) Uani 1 1 d . . . C9 C 0.1018(4) 0.8602(5) 0.91829(10) 0.0344(10) Uani 1 1 d . . . H9 H 0.1124 0.8226 0.9364 0.041 Uiso 1 1 calc R . . C10 C 0.1920(4) 0.8414(5) 0.89682(11) 0.0375(12) Uani 1 1 d . . . H10 H 0.2617 0.7912 0.9005 0.045 Uiso 1 1 calc R . . C11 C 0.1778(4) 0.8953(4) 0.87131(11) 0.0341(11) Uani 1 1 d . . . H11 H 0.2393 0.8839 0.8572 0.041 Uiso 1 1 calc R . . C12 C 0.0745(5) 0.9681(4) 0.86482(9) 0.0305(9) Uani 1 1 d . . . C13 C 0.0585(5) 1.0231(5) 0.83777(10) 0.0358(11) Uani 1 1 d . . . H13 H 0.1184 1.0096 0.8234 0.043 Uiso 1 1 calc R . . C14 C -0.0403(5) 1.0942(5) 0.83198(10) 0.0400(12) Uani 1 1 d . . . H14 H -0.0487 1.1306 0.8137 0.048 Uiso 1 1 calc R . . C15 C -0.1306(5) 1.1143(5) 0.85284(10) 0.0345(10) Uani 1 1 d . . . H15 H -0.2003 1.1635 0.8486 0.041 Uiso 1 1 calc R . . C16 C -0.1187(4) 1.0635(4) 0.87931(10) 0.0297(10) Uani 1 1 d . . . H16 H -0.1799 1.0789 0.8933 0.036 Uiso 1 1 calc R . . C17 C -0.0164(4) 0.9880(4) 0.88629(9) 0.0249(9) Uani 1 1 d . . . S1' S 0.14206(10) 0.98956(10) 0.76090(2) 0.0259(2) Uani 1 1 d . . . S2' S 0.13678(11) 1.26671(10) 0.76136(2) 0.0273(2) Uani 1 1 d . . . N1' N 0.4225(3) 1.1315(4) 0.80300(7) 0.0248(7) Uani 1 1 d . . . C1' C 0.0590(4) 1.1272(4) 0.75470(8) 0.0243(8) Uani 1 1 d . . . C2' C 0.2614(4) 1.0651(4) 0.77872(8) 0.0228(8) Uani 1 1 d . . . C3' C 0.2602(4) 1.1943(4) 0.77891(9) 0.0254(9) Uani 1 1 d . . . C4' C 0.3643(4) 1.0292(4) 0.79347(9) 0.0260(9) Uani 1 1 d . . . H4' H 0.3903 0.9469 0.7965 0.031 Uiso 1 1 calc R . . C5' C 0.3604(4) 1.2349(4) 0.79394(9) 0.0250(8) Uani 1 1 d . . . H5' H 0.3827 1.3178 0.7974 0.030 Uiso 1 1 calc R . . C6' C 0.5481(4) 1.1362(5) 0.81543(8) 0.0258(8) Uani 1 1 d . . . H6' H 0.5567 1.2164 0.8256 0.031 Uiso 1 1 calc R . . C7' C 0.6412(5) 1.1348(6) 0.79126(10) 0.0417(11) Uani 1 1 d . . . H7'A H 0.6290 1.2071 0.7792 0.063 Uiso 1 1 calc R . . H7'B H 0.6299 1.0603 0.7799 0.063 Uiso 1 1 calc R . . H7'C H 0.7247 1.1359 0.7991 0.063 Uiso 1 1 calc R . . C8' C 0.5627(4) 1.0342(4) 0.83738(9) 0.0253(9) Uani 1 1 d . . . C9' C 0.6323(5) 0.9323(5) 0.83183(11) 0.0367(11) Uani 1 1 d . . . H9' H 0.6715 0.9254 0.8138 0.044 Uiso 1 1 calc R . . C10' C 0.6480(5) 0.8371(5) 0.85184(12) 0.0423(12) Uani 1 1 d . . . H10' H 0.6959 0.7670 0.8471 0.051 Uiso 1 1 calc R . . C11' C 0.5941(5) 0.8460(5) 0.87810(12) 0.0411(12) Uani 1 1 d . . . H11' H 0.6038 0.7817 0.8916 0.049 Uiso 1 1 calc R . . C12' C 0.5234(5) 0.9519(5) 0.88519(10) 0.0331(11) Uani 1 1 d . . . C13' C 0.4694(5) 0.9624(5) 0.91243(10) 0.0414(12) Uani 1 1 d . . . H13' H 0.4844 0.9008 0.9263 0.050 Uiso 1 1 calc R . . C14' C 0.3958(5) 1.0603(5) 0.91907(10) 0.0421(13) Uani 1 1 d . . . H14' H 0.3594 1.0660 0.9374 0.051 Uiso 1 1 calc R . . C15' C 0.3739(5) 1.1529(5) 0.89865(10) 0.0351(11) Uani 1 1 d . . . H15' H 0.3223 1.2206 0.9031 0.042 Uiso 1 1 calc R . . C16' C 0.4278(4) 1.1439(4) 0.87230(9) 0.0298(9) Uani 1 1 d . . . H16' H 0.4129 1.2068 0.8587 0.036 Uiso 1 1 calc R . . C17' C 0.5044(4) 1.0451(4) 0.86464(9) 0.0257(9) 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 S1 0.0285(5) 0.0265(5) 0.0287(5) -0.0054(5) -0.0017(4) 0.0019(5) S2 0.0301(5) 0.0271(5) 0.0286(5) -0.0048(5) -0.0039(4) 0.0018(5) N1 0.0330(19) 0.0256(17) 0.0197(16) -0.0037(14) 0.0008(15) -0.0022(16) C1 0.035(2) 0.023(2) 0.0211(19) -0.0026(15) -0.0057(18) 0.0022(19) C2 0.031(2) 0.025(2) 0.0199(19) 0.0028(16) 0.0007(17) 0.0031(18) C3 0.035(2) 0.023(2) 0.0171(18) -0.0003(16) -0.0021(17) 0.0003(18) C4 0.038(2) 0.029(2) 0.0198(19) 0.0014(18) -0.0022(17) 0.000(2) C5 0.0250(19) 0.025(2) 0.0217(18) 0.0023(18) -0.0026(15) 0.0001(19) C6 0.035(2) 0.025(2) 0.022(2) -0.0022(16) 0.0048(18) -0.0016(19) C7 0.058(3) 0.031(2) 0.031(2) 0.002(2) 0.008(2) -0.002(3) C8 0.032(2) 0.024(2) 0.023(2) -0.0050(17) -0.0015(17) -0.0017(18) C9 0.037(2) 0.036(2) 0.031(2) -0.009(2) -0.0051(18) 0.004(2) C10 0.025(2) 0.039(3) 0.048(3) -0.007(2) -0.003(2) 0.006(2) C11 0.029(2) 0.032(3) 0.041(3) -0.007(2) 0.0045(19) -0.0008(19) C12 0.029(2) 0.037(2) 0.026(2) -0.0093(18) 0.0052(19) -0.005(2) C13 0.035(3) 0.044(3) 0.028(2) -0.004(2) 0.013(2) -0.007(2) C14 0.052(3) 0.048(3) 0.020(2) 0.0052(19) 0.000(2) -0.004(2) C15 0.034(2) 0.041(3) 0.028(2) 0.002(2) -0.0054(19) 0.008(2) C16 0.028(2) 0.036(2) 0.024(2) -0.0052(18) 0.0008(17) -0.0076(19) C17 0.028(2) 0.025(2) 0.0218(19) -0.0040(17) -0.0014(16) -0.0040(17) S1' 0.0255(5) 0.0261(5) 0.0261(5) -0.0030(4) -0.0032(4) 0.0012(4) S2' 0.0256(5) 0.0259(5) 0.0303(5) -0.0015(4) -0.0067(5) 0.0012(4) N1' 0.0224(16) 0.0305(17) 0.0214(15) -0.0027(15) -0.0013(13) 0.0022(18) C1' 0.0222(19) 0.030(2) 0.0211(18) -0.0005(17) 0.0010(14) -0.0051(19) C2' 0.023(2) 0.027(2) 0.0184(19) -0.0014(16) -0.0020(16) 0.0022(17) C3' 0.026(2) 0.029(2) 0.021(2) -0.0002(17) 0.0031(17) 0.0044(18) C4' 0.0243(19) 0.034(2) 0.0194(19) -0.0007(17) -0.0021(17) 0.0028(19) C5' 0.027(2) 0.024(2) 0.024(2) 0.0013(16) -0.0021(18) 0.0005(19) C6' 0.0213(18) 0.033(2) 0.0233(19) 0.0024(18) -0.0020(15) -0.0005(19) C7' 0.031(2) 0.066(3) 0.028(2) 0.006(3) 0.0000(19) -0.001(3) C8' 0.021(2) 0.027(2) 0.028(2) -0.0002(16) -0.0081(17) -0.0017(17) C9' 0.027(2) 0.045(3) 0.038(3) -0.009(2) -0.010(2) 0.003(2) C10' 0.037(3) 0.033(3) 0.057(3) -0.004(2) -0.016(3) 0.006(2) C11' 0.045(3) 0.031(3) 0.047(3) 0.013(2) -0.017(2) -0.004(2) C12' 0.033(2) 0.034(3) 0.033(2) 0.003(2) -0.005(2) -0.011(2) C13' 0.053(3) 0.045(3) 0.027(2) 0.012(2) -0.007(2) -0.015(3) C14' 0.053(3) 0.052(3) 0.021(2) 0.001(2) 0.001(2) -0.011(3) C15' 0.042(3) 0.037(3) 0.026(2) -0.0046(19) 0.0019(19) -0.007(2) C16' 0.032(2) 0.032(2) 0.025(2) 0.0045(18) -0.0044(18) -0.003(2) C17' 0.026(2) 0.028(2) 0.023(2) 0.0008(17) -0.0055(16) -0.0076(18) _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 C2 1.744(4) . ? S1 C1 1.783(5) . ? S2 C3 1.757(5) . ? S2 C1 1.761(5) . ? N1 C5 1.369(6) . ? N1 C4 1.371(6) . ? N1 C6 1.491(5) . ? C1 C1 1.351(8) 3_587 ? C2 C4 1.369(7) . ? C2 C3 1.417(6) . ? C3 C5 1.368(6) . ? C6 C8 1.522(6) . ? C6 C7 1.532(6) . ? C8 C9 1.365(7) . ? C8 C17 1.435(6) . ? C9 C10 1.422(7) . ? C10 C11 1.344(7) . ? C11 C12 1.408(7) . ? C12 C13 1.416(7) . ? C12 C17 1.428(6) . ? C13 C14 1.352(8) . ? C14 C15 1.404(7) . ? C15 C16 1.368(6) . ? C16 C17 1.421(6) . ? S1' C2' 1.750(4) . ? S1' C1' 1.774(5) . ? S2' C3' 1.761(5) . ? S2' C1' 1.768(5) . ? N1' C4' 1.358(6) . ? N1' C5' 1.381(6) . ? N1' C6' 1.485(5) . ? C1' C1' 1.356(8) 4_556 ? C2' C4' 1.373(6) . ? C2' C3' 1.408(6) . ? C3' C5' 1.371(6) . ? C6' C7' 1.521(6) . ? C6' C8' 1.525(6) . ? C8' C9' 1.368(7) . ? C8' C17' 1.434(6) . ? C9' C10' 1.410(7) . ? C10' C11' 1.370(8) . ? C11' C12' 1.426(7) . ? C12' C13' 1.413(7) . ? C12' C17' 1.417(6) . ? C13' C14' 1.369(8) . ? C14' C15' 1.413(7) . ? C15' C16' 1.373(6) . ? C16' C17' 1.407(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C1 94.0(2) . . ? C3 S2 C1 93.7(2) . . ? C5 N1 C4 110.5(3) . . ? C5 N1 C6 124.9(4) . . ? C4 N1 C6 123.0(4) . . ? C1 C1 S2 122.96(15) 3_587 . ? C1 C1 S1 120.08(14) 3_587 . ? S2 C1 S1 117.0(2) . . ? C4 C2 C3 107.5(4) . . ? C4 C2 S1 135.6(4) . . ? C3 C2 S1 117.0(3) . . ? C5 C3 C2 108.0(4) . . ? C5 C3 S2 134.3(4) . . ? C2 C3 S2 117.6(3) . . ? C2 C4 N1 107.1(4) . . ? C3 C5 N1 106.8(4) . . ? N1 C6 C8 110.1(4) . . ? N1 C6 C7 108.2(4) . . ? C8 C6 C7 115.3(4) . . ? C9 C8 C17 119.5(4) . . ? C9 C8 C6 121.4(4) . . ? C17 C8 C6 119.1(4) . . ? C8 C9 C10 121.5(5) . . ? C11 C10 C9 119.4(5) . . ? C10 C11 C12 122.1(4) . . ? C11 C12 C13 122.0(4) . . ? C11 C12 C17 118.9(4) . . ? C13 C12 C17 119.1(5) . . ? C14 C13 C12 121.4(5) . . ? C13 C14 C15 120.2(4) . . ? C16 C15 C14 120.4(5) . . ? C15 C16 C17 121.2(4) . . ? C16 C17 C12 117.7(4) . . ? C16 C17 C8 123.7(4) . . ? C12 C17 C8 118.6(4) . . ? C2' S1' C1' 93.3(2) . . ? C3' S2' C1' 93.5(2) . . ? C4' N1' C5' 109.9(3) . . ? C4' N1' C6' 125.9(4) . . ? C5' N1' C6' 122.8(4) . . ? C1' C1' S2' 120.66(14) 4_556 . ? C1' C1' S1' 122.31(13) 4_556 . ? S2' C1' S1' 117.0(2) . . ? C4' C2' C3' 106.9(4) . . ? C4' C2' S1' 135.3(4) . . ? C3' C2' S1' 117.8(4) . . ? C5' C3' C2' 108.5(4) . . ? C5' C3' S2' 134.6(4) . . ? C2' C3' S2' 116.9(4) . . ? N1' C4' C2' 108.2(4) . . ? C3' C5' N1' 106.5(4) . . ? N1' C6' C7' 108.5(3) . . ? N1' C6' C8' 109.7(4) . . ? C7' C6' C8' 115.4(4) . . ? C9' C8' C17' 118.8(4) . . ? C9' C8' C6' 121.4(4) . . ? C17' C8' C6' 119.8(4) . . ? C8' C9' C10' 122.5(5) . . ? C11' C10' C9' 119.8(5) . . ? C10' C11' C12' 119.9(4) . . ? C13' C12' C17' 120.0(5) . . ? C13' C12' C11' 120.1(5) . . ? C17' C12' C11' 120.0(5) . . ? C14' C13' C12' 120.8(5) . . ? C13' C14' C15' 120.0(5) . . ? C16' C15' C14' 119.3(5) . . ? C15' C16' C17' 122.5(4) . . ? C16' C17' C12' 117.4(4) . . ? C16' C17' C8' 123.6(4) . . ? C12' C17' C8' 119.0(4) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.510 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.111