# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 1145/174 data_global _publ_contact_author ; Dr Marc Fourmigu\'e Institut des Mat\'eriaux Jean Rouxel UMR 6502 CNRS-Universit\'e de Nantes 2; rue de la Houssini\`ere, BP32229 44322 Nantes cedex 3, France ; _publ_contact_author_email fourmigue@cnrs-imn.fr _publ_contact_letter ; Please find enclosed , in CIF format, data corresponding to four crystal structures reported in a paper we are submitting to J. Mater. Chem entitled: A delicate balance of N-H...O, C-H...O hydrogen bonds and S...S van der Waals interactions. The crystal chemistry of amide- functionalized ethylendithiotetrathiafulvalenes: EDT-TTF-CONRR' (R, R' = H, Me) by Karine Heuze, Marc Fourmigue and Patrick Batail The original manuscript has been sent by post today. With best regards Marc Fourmigue ; data_acid _audit_creation_method SHELXL _chemical_name_systematic ; 4-(4',5'-ethylenedithiotetrathiafulvalenyl)carboxylic acid ; _chemical_name_common 'EDT-TTF-CO2H' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C9 H6 O2 S6' _chemical_formula_weight 338.50 _chemical_melting_point ? _chemical_compound_source ? 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.3720(8) _cell_length_b 27.142(6) _cell_length_c 14.238(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.29(2) _cell_angle_gamma 90.00 _cell_volume 2460.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 2109 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 24.9 _exptl_crystal_description 'needle' _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.828 _exptl_crystal_density_method ? _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'area detector' _diffrn_detector_area_resol_mean 6.66 _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method 'Oscillation, phi incr. 0.9' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19288 _diffrn_reflns_av_R_equivalents 0.4439 _diffrn_reflns_av_sigmaI/netI 0.5141 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.90 _reflns_number_total 4613 _reflns_number_observed 1035 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'EXPOSE (Stoe IPDS)' _computing_cell_refinement 'CELL (Stoe IPDS)' _computing_data_reduction 'INTEGRATE (Stoe IPDS)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0000P)^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_number_reflns 4612 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2866 _refine_ls_R_factor_obs 0.0819 _refine_ls_wR_factor_all 0.1902 _refine_ls_wR_factor_obs 0.1232 _refine_ls_goodness_of_fit_all 0.712 _refine_ls_goodness_of_fit_obs 1.040 _refine_ls_restrained_S_all 0.716 _refine_ls_restrained_S_obs 1.040 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.9112(7) 0.1188(2) 0.1604(3) 0.0422(13) Uani 1 d . . S2 S 0.4784(7) 0.1128(2) 0.2263(3) 0.0410(12) Uani 1 d . . S3 S 1.0444(7) 0.1856(2) 0.3386(3) 0.0449(13) Uani 1 d . . S4 S 0.6154(7) 0.1778(2) 0.4090(3) 0.0398(12) Uani 1 d . . S5 S 1.1858(7) 0.2583(2) 0.4819(3) 0.0522(14) Uani 1 d . . S6 S 0.6958(7) 0.2466(2) 0.5674(3) 0.0505(13) Uani 1 d . . C1 C 0.7977(31) 0.0642(7) 0.0059(12) 0.051(5) Uiso 1 d . . C2 C 0.7206(28) 0.0882(6) 0.0906(11) 0.046(5) Uiso 1 d . . C3 C 0.5206(28) 0.0860(6) 0.1198(11) 0.045(4) Uiso 1 d . . H3 H 0.4133(28) 0.0708(6) 0.0843(11) 0.054 Uiso 1 calc R . C4 C 0.7364(24) 0.1374(5) 0.2458(9) 0.030(4) Uiso 1 d . . C5 C 0.7911(25) 0.1650(5) 0.3194(10) 0.032(4) Uiso 1 d . . C6 C 0.9808(25) 0.2232(6) 0.4353(10) 0.034(4) Uiso 1 d . . C7 C 0.7855(24) 0.2185(5) 0.4651(9) 0.031(4) Uiso 1 d . . C8 C 1.1147(45) 0.2651(10) 0.5951(17) 0.110(9) Uiso 1 d . . H8A H 1.2253(45) 0.2491(10) 0.6326(17) 0.131 Uiso 1 calc R . H8B H 1.1292(45) 0.3001(10) 0.6080(17) 0.131 Uiso 1 calc R . C9 C 0.9283(31) 0.2513(8) 0.6366(13) 0.067(6) Uiso 1 d . . H9A H 0.9033(31) 0.2748(8) 0.6863(13) 0.080 Uiso 1 calc R . H9B H 0.9527(31) 0.2196(8) 0.6665(13) 0.080 Uiso 1 calc R . O1 O 0.6483(19) 0.0442(4) -0.0497(7) 0.049(3) Uiso 1 d . . O2 O 0.9872(20) 0.0620(4) -0.0077(8) 0.056(3) Uiso 1 d . . S7 S 1.1163(7) 0.0464(2) 0.3725(3) 0.0380(12) Uani 1 d . . S8 S 0.6791(7) 0.0389(2) 0.4336(3) 0.0402(13) Uani 1 d . . S9 S 1.2420(7) 0.1067(2) 0.5612(3) 0.0398(12) Uani 1 d . . S10 S 0.8076(7) 0.0988(2) 0.6223(3) 0.0446(13) Uani 1 d . . S11 S 1.4057(8) 0.1515(3) 0.7350(4) 0.092(2) Uani 1 d . . S12 S 0.8928(7) 0.1421(2) 0.8095(3) 0.058(2) Uani 1 d . . C10 C 1.0006(26) -0.0046(6) 0.2139(11) 0.037(4) Uiso 1 d . . C11 C 0.9321(24) 0.0144(6) 0.3019(10) 0.032(4) Uiso 1 d . . C12 C 0.7389(28) 0.0127(6) 0.3326(11) 0.045(4) Uiso 1 d . . H12 H 0.6345(28) -0.0034(6) 0.2969(11) 0.054 Uiso 1 calc R . C13 C 0.9398(24) 0.0611(6) 0.4580(10) 0.031(4) Uiso 1 d . . C14 C 0.9903(22) 0.0849(5) 0.5347(9) 0.022(3) Uiso 1 d . . C15 C 1.1853(26) 0.1259(6) 0.6738(10) 0.040(4) Uiso 1 d . . C16 C 0.9851(24) 0.1223(6) 0.7003(10) 0.034(4) Uiso 1 d . . C17 C 1.3218(29) 0.1450(7) 0.8545(11) 0.055(5) Uiso 1 d . . H17A H 1.3157(29) 0.1102(7) 0.8702(11) 0.066 Uiso 1 calc R . H17B H 1.4247(29) 0.1603(7) 0.8971(11) 0.066 Uiso 1 calc R . C18 C 1.1144(28) 0.1674(6) 0.8679(11) 0.047(5) Uiso 1 d . . H18A H 1.1230(28) 0.2018(6) 0.8494(11) 0.057 Uiso 1 calc R . H18B H 1.0898(28) 0.1669(6) 0.9347(11) 0.057 Uiso 1 calc R . O3 O 0.8633(19) -0.0236(4) 0.1566(7) 0.049(3) Uiso 1 d . . O4 O 1.1944(17) -0.0025(4) 0.1950(7) 0.041(3) Uiso 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 0.032(3) 0.063(3) 0.032(2) -0.015(2) 0.010(2) -0.001(2) S2 0.036(3) 0.053(3) 0.035(2) -0.009(2) 0.012(2) -0.003(2) S3 0.027(3) 0.071(4) 0.038(2) -0.016(2) 0.013(2) -0.006(2) S4 0.030(3) 0.056(3) 0.035(2) -0.007(2) 0.014(2) -0.002(2) S5 0.036(3) 0.077(4) 0.044(2) -0.007(2) 0.004(2) -0.015(3) S6 0.037(3) 0.081(4) 0.033(2) -0.022(2) 0.008(2) 0.009(3) S7 0.029(3) 0.051(3) 0.035(2) -0.008(2) 0.010(2) -0.005(2) S8 0.024(3) 0.065(4) 0.032(2) -0.007(2) 0.007(2) -0.006(2) S9 0.031(3) 0.054(3) 0.035(2) -0.007(2) 0.010(2) -0.004(2) S10 0.023(2) 0.069(4) 0.042(2) -0.015(2) 0.007(2) -0.006(2) S11 0.034(3) 0.181(7) 0.062(3) -0.064(4) 0.019(3) -0.031(4) S12 0.034(3) 0.097(4) 0.045(3) -0.030(3) 0.013(2) -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 1.75(2) . ? S1 C4 1.755(14) . ? S2 C3 1.71(2) . ? S2 C4 1.78(2) . ? S3 C5 1.72(2) . ? S3 C6 1.774(15) . ? S4 C7 1.72(2) . ? S4 C5 1.765(14) . ? S5 C8 1.70(2) . ? S5 C6 1.73(2) . ? S6 C9 1.75(2) . ? S6 C7 1.760(14) . ? C1 O2 1.23(2) . ? C1 O1 1.33(2) . ? C1 C2 1.47(2) . ? C2 C3 1.36(2) . ? C4 C5 1.32(2) . ? C6 C7 1.34(2) . ? C8 C9 1.40(3) . ? S7 C13 1.736(14) . ? S7 C11 1.75(2) . ? S8 C12 1.66(2) . ? S8 C13 1.79(2) . ? S9 C14 1.737(15) . ? S9 C15 1.738(14) . ? S10 C16 1.68(2) . ? S10 C14 1.780(13) . ? S11 C15 1.77(2) . ? S11 C17 1.81(2) . ? S12 C18 1.75(2) . ? S12 C16 1.767(14) . ? C10 O4 1.28(2) . ? C10 O3 1.28(2) . ? C10 C11 1.44(2) . ? C11 C12 1.32(2) . ? C13 C14 1.30(2) . ? C15 C16 1.35(2) . ? C17 C18 1.47(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C4 94.8(8) . . ? C3 S2 C4 96.9(8) . . ? C5 S3 C6 93.9(7) . . ? C7 S4 C5 93.2(7) . . ? C8 S5 C6 101.4(11) . . ? C9 S6 C7 101.6(8) . . ? O2 C1 O1 124.8(16) . . ? O2 C1 C2 120.7(17) . . ? O1 C1 C2 114.5(15) . . ? C3 C2 C1 125.4(17) . . ? C3 C2 S1 119.1(13) . . ? C1 C2 S1 115.4(13) . . ? C2 C3 S2 115.8(14) . . ? C5 C4 S1 123.8(12) . . ? C5 C4 S2 123.1(11) . . ? S1 C4 S2 113.0(8) . . ? C4 C5 S3 121.7(11) . . ? C4 C5 S4 122.0(12) . . ? S3 C5 S4 116.1(8) . . ? C7 C6 S5 129.0(12) . . ? C7 C6 S3 115.9(12) . . ? S5 C6 S3 115.0(8) . . ? C6 C7 S4 119.4(11) . . ? C6 C7 S6 124.0(12) . . ? S4 C7 S6 116.3(8) . . ? C9 C8 S5 129.3(21) . . ? C8 C9 S6 119.7(17) . . ? C13 S7 C11 94.5(7) . . ? C12 S8 C13 93.9(8) . . ? C14 S9 C15 94.5(7) . . ? C16 S10 C14 95.8(7) . . ? C15 S11 C17 99.6(8) . . ? C18 S12 C16 104.3(8) . . ? O4 C10 O3 121.6(14) . . ? O4 C10 C11 119.9(15) . . ? O3 C10 C11 118.5(14) . . ? C12 C11 C10 126.4(16) . . ? C12 C11 S7 116.1(13) . . ? C10 C11 S7 117.4(11) . . ? C11 C12 S8 121.3(15) . . ? C14 C13 S7 123.9(12) . . ? C14 C13 S8 121.9(11) . . ? S7 C13 S8 114.2(8) . . ? C13 C14 S9 123.2(11) . . ? C13 C14 S10 123.2(11) . . ? S9 C14 S10 113.6(8) . . ? C16 C15 S9 118.1(13) . . ? C16 C15 S11 129.3(12) . . ? S9 C15 S11 112.5(9) . . ? C15 C16 S10 117.5(11) . . ? C15 C16 S12 125.2(13) . . ? S10 C16 S12 117.3(9) . . ? C18 C17 S11 112.3(13) . . ? C17 C18 S12 119.1(13) . . ? _refine_diff_density_max 0.563 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.100 #===END data_AMI _audit_creation_method SHELXL _chemical_name_systematic ; 3-amido-3',4'-ethylenedithiotetrathiafulvalene, THF solvate ; _chemical_name_common 'EDT-TTF-CONH2, 0.75 THF' _chemical_formula_moiety 'C9 H7 N O S6, 0.75(C4 H8 O)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H13 N O1.75 S6' _chemical_formula_weight 391.59 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.3477(6) _cell_length_b 30.765(3) _cell_length_c 16.438(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.681(11) _cell_angle_gamma 90.00 _cell_volume 3194.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 25.7 _exptl_crystal_description 'needle' _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.628 _exptl_crystal_density_method ? _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.855 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'area detector' _diffrn_measurement_device_type 'Stoe-IPDS' _diffrn_detector_area_resol_mean 6.66 _diffrn_measurement_method 'Oscillation, phi incr. 0.7' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23683 _diffrn_reflns_av_R_equivalents 0.2173 _diffrn_reflns_av_sigmaI/netI 0.2480 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.91 _reflns_number_total 6153 _reflns_number_observed 2399 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'EXPOSE (Stoe-IPDS)' _computing_cell_refinement 'SELECT (Stoe-IPDS)' _computing_data_reduction 'INTEGRATE (Stoe-IPDS)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0427P)^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_number_reflns 6153 _refine_ls_number_parameters 378 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1899 _refine_ls_R_factor_obs 0.0689 _refine_ls_wR_factor_all 0.1512 _refine_ls_wR_factor_obs 0.1173 _refine_ls_goodness_of_fit_all 0.827 _refine_ls_goodness_of_fit_obs 1.074 _refine_ls_restrained_S_all 0.827 _refine_ls_restrained_S_obs 1.074 _refine_ls_shift/esd_max 0.019 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.7691(3) 0.14574(6) 0.35970(11) 0.0297(5) Uani 1 d . . S2 S 0.3115(3) 0.15539(7) 0.30930(12) 0.0340(5) Uani 1 d . . S3 S 0.8689(3) 0.21927(7) 0.22873(12) 0.0353(5) Uani 1 d . . S4 S 0.4159(3) 0.22872(7) 0.17741(12) 0.0388(6) Uani 1 d . . S5 S 0.9835(4) 0.30535(8) 0.1687(2) 0.0529(7) Uani 1 d . . S6 S 0.4721(4) 0.31688(8) 0.10267(15) 0.0504(7) Uani 1 d . . C1 C 0.6945(13) 0.0815(2) 0.4661(4) 0.028(2) Uani 1 d . . C2 C 0.5918(12) 0.1123(2) 0.4047(4) 0.026(2) Uani 1 d . . C3 C 0.3859(13) 0.1169(2) 0.3807(4) 0.030(2) Uani 1 d . . H3 H 0.2858(13) 0.0994(2) 0.4024(4) 0.036 Uiso 1 calc R . C4 C 0.5697(11) 0.1717(2) 0.2965(4) 0.024(2) Uani 1 d . . C5 C 0.6129(12) 0.2023(2) 0.2417(4) 0.031(2) Uani 1 d . . C6 C 0.7851(12) 0.2687(3) 0.1824(4) 0.030(2) Uani 1 d . . C7 C 0.5808(13) 0.2728(3) 0.1587(4) 0.034(2) Uani 1 d . . C9 C 0.6793(14) 0.3240(3) 0.0387(6) 0.059(3) Uani 1 d . . H9A H 0.6919(14) 0.2975(3) 0.0077(6) 0.071 Uiso 1 calc R . H9B H 0.6378(14) 0.3470(3) -0.0001(6) 0.071 Uiso 1 calc R . C8 C 0.8837(15) 0.3345(4) 0.0784(6) 0.069(3) Uani 1 d . . H8A H 0.8824(15) 0.3651(4) 0.0925(6) 0.082 Uiso 1 calc R . H8B H 0.9852(15) 0.3310(4) 0.0385(6) 0.082 Uiso 1 calc R . O1 O 0.8836(9) 0.0854(2) 0.4866(3) 0.0366(14) Uani 1 d . . N1 N 0.5760(10) 0.0510(2) 0.4952(3) 0.033(2) Uani 1 d . . H1A H 0.6318(10) 0.0326(2) 0.5303(3) 0.040 Uiso 1 calc R . H1B H 0.4432(10) 0.0495(2) 0.4789(3) 0.040 Uiso 1 calc R . S7 S 0.0622(3) 0.05694(7) 0.23828(11) 0.0331(5) Uani 1 d . . S8 S -0.3988(3) 0.06391(7) 0.19427(11) 0.0336(5) Uani 1 d . . S9 S 0.1391(3) 0.12586(8) 0.09349(12) 0.0417(6) Uani 1 d . . S10 S -0.3217(3) 0.13306(8) 0.05339(13) 0.0441(6) Uani 1 d . . S11A S 0.2303(8) 0.2015(3) -0.0115(4) 0.062(3) Uani 0.74(2) d P . S11B S 0.2436(19) 0.1727(8) -0.0490(12) 0.060(7) Uani 0.26(2) d P . S12 S -0.2859(4) 0.20523(9) -0.06630(15) 0.0603(8) Uani 1 d . . C10 C 0.0066(13) 0.0039(2) 0.3682(4) 0.028(2) Uani 1 d . . C11 C -0.1064(12) 0.0290(2) 0.2986(4) 0.028(2) Uani 1 d . . C12 C -0.3126(12) 0.0326(2) 0.2777(4) 0.028(2) Uani 1 d . . H12 H -0.4090(12) 0.0185(2) 0.3076(4) 0.033 Uiso 1 calc R . C13 C -0.1454(12) 0.0814(2) 0.1752(4) 0.028(2) Uani 1 d . . C14 C -0.1137(12) 0.1105(2) 0.1174(4) 0.029(2) Uani 1 d . . C15 C 0.0415(16) 0.1663(3) 0.0234(5) 0.060(3) Uani 1 d . . C16 C -0.1612(14) 0.1690(3) 0.0046(5) 0.039(2) Uani 1 d . . C17A C 0.1210(40) 0.2272(10) -0.0914(15) 0.067(4) Uiso 0.44(2) d P . C17B C 0.1167(32) 0.2002(8) -0.1196(12) 0.067(4) Uiso 0.56(2) d P . C18 C -0.0871(22) 0.2180(6) -0.1297(8) 0.140(7) Uani 1 d . . N2 N -0.1077(11) -0.0271(2) 0.3991(3) 0.038(2) Uani 1 d . . H2A H -0.0533(11) -0.0427(2) 0.4394(3) 0.045 Uiso 1 calc R . H2B H -0.2360(11) -0.0316(2) 0.3789(3) 0.045 Uiso 1 calc R . O2 O 0.1915(8) 0.0129(2) 0.3929(3) 0.0334(13) Uani 1 d . . O3 O -0.4354(10) -0.0714(2) 0.2974(3) 0.055(2) Uani 1 d . . C19 C -0.6535(17) -0.0733(4) 0.2699(7) 0.079(4) Uani 1 d . . H19A H -0.7094(17) -0.0441(4) 0.2615(7) 0.095 Uiso 1 calc R . H19B H -0.7301(17) -0.0875(4) 0.3106(7) 0.095 Uiso 1 calc R . C20 C -0.6819(25) -0.0978(5) 0.1926(8) 0.126(6) Uani 1 d . . H20A H -0.8016(25) -0.0871(5) 0.1569(8) 0.151 Uiso 1 calc R . H20B H -0.6993(25) -0.1287(5) 0.2020(8) 0.151 Uiso 1 calc R . C21 C -0.3245(16) -0.0844(3) 0.2316(5) 0.075(3) Uani 1 d . . H21A H -0.2558(16) -0.1122(3) 0.2435(5) 0.090 Uiso 1 calc R . H21B H -0.2167(16) -0.0631(3) 0.2223(5) 0.090 Uiso 1 calc R . C22 C -0.4761(16) -0.0881(3) 0.1591(5) 0.144(7) Uani 1 d R . H22A H -0.4369(16) -0.1115(3) 0.1239(5) 0.172 Uiso 1 calc R . H22B H -0.4845(16) -0.0612(3) 0.1283(5) 0.172 Uiso 1 calc R . O4 O 0.0544(42) 0.0225(7) 0.9407(11) 0.096(6) Uiso 0.50 d P . C23 C 0.1871(48) -0.0057(12) 1.0169(21) 0.076(8) Uiso 0.50 d P . C24 C 0.0714(100) -0.0300(16) 1.0354(30) 0.165(17) Uiso 0.50 d P . C25 C -0.1859(78) -0.0142(16) 1.0142(33) 0.149(17) Uiso 0.50 d P . C26 C -0.1595(51) 0.0054(10) 0.9340(19) 0.097(9) Uiso 0.50 d P . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0285(12) 0.0282(11) 0.0325(11) 0.0120(9) 0.0028(9) -0.0002(9) S2 0.0309(13) 0.0344(12) 0.0365(12) 0.0151(9) 0.0016(9) -0.0006(10) S3 0.0303(13) 0.0327(12) 0.0447(12) 0.0175(10) 0.0124(10) 0.0055(10) S4 0.0349(13) 0.0366(13) 0.0437(13) 0.0207(10) -0.0013(10) -0.0032(11) S5 0.0385(14) 0.049(2) 0.069(2) 0.0337(12) -0.0045(12) -0.0099(12) S6 0.0397(14) 0.0497(15) 0.064(2) 0.0374(12) 0.0171(12) 0.0120(12) C1 0.038(5) 0.022(4) 0.023(4) -0.008(3) -0.001(4) -0.001(4) C2 0.038(5) 0.022(4) 0.017(4) 0.004(3) 0.002(3) -0.002(4) C3 0.038(5) 0.028(4) 0.025(4) -0.003(3) 0.010(4) -0.004(4) C4 0.025(4) 0.021(4) 0.025(4) -0.004(3) -0.002(3) 0.001(3) C5 0.039(5) 0.022(4) 0.034(4) -0.001(3) 0.010(4) -0.006(4) C6 0.028(5) 0.036(5) 0.027(4) 0.008(3) 0.011(3) -0.003(4) C7 0.034(5) 0.036(5) 0.031(4) 0.010(4) 0.007(4) 0.004(4) C9 0.042(6) 0.074(7) 0.064(6) 0.036(5) 0.017(5) 0.015(6) C8 0.045(6) 0.096(9) 0.063(7) 0.043(6) -0.003(5) -0.007(6) O1 0.037(4) 0.034(3) 0.035(3) 0.017(2) -0.014(3) -0.008(3) N1 0.037(4) 0.029(4) 0.031(4) 0.018(3) -0.007(3) -0.011(3) S7 0.0283(12) 0.0424(13) 0.0286(11) 0.0151(9) 0.0029(9) -0.0007(10) S8 0.0305(12) 0.0404(12) 0.0288(11) 0.0136(9) -0.0030(9) -0.0007(10) S9 0.0361(13) 0.0575(15) 0.0317(11) 0.0214(10) 0.0046(10) -0.0009(12) S10 0.0340(13) 0.0564(15) 0.0418(13) 0.0296(11) 0.0032(10) 0.0004(12) S11A 0.057(3) 0.080(5) 0.046(3) 0.037(3) -0.002(2) -0.025(3) S11B 0.040(6) 0.082(14) 0.061(10) 0.044(10) 0.027(6) 0.021(7) S12 0.058(2) 0.064(2) 0.057(2) 0.0381(13) -0.0014(13) 0.0001(14) C10 0.036(5) 0.027(4) 0.021(4) 0.003(3) -0.003(4) -0.001(4) C11 0.035(5) 0.031(5) 0.018(4) -0.003(3) 0.003(3) -0.001(4) C12 0.031(5) 0.033(5) 0.019(4) 0.009(3) -0.001(3) -0.007(4) C13 0.036(5) 0.026(4) 0.023(4) -0.002(3) 0.004(3) -0.006(4) C14 0.036(5) 0.032(5) 0.019(4) 0.006(3) 0.008(3) -0.004(4) C15 0.050(7) 0.087(8) 0.043(6) 0.037(5) 0.004(5) -0.011(6) C16 0.037(5) 0.049(6) 0.032(4) 0.025(4) 0.006(4) 0.002(4) C18 0.076(10) 0.248(21) 0.100(10) 0.100(12) 0.025(8) -0.007(12) N2 0.045(4) 0.042(4) 0.023(3) 0.016(3) -0.006(3) -0.008(4) O2 0.032(3) 0.036(3) 0.029(3) 0.004(2) -0.010(2) -0.004(3) O3 0.062(5) 0.053(4) 0.048(4) -0.017(3) 0.004(3) -0.016(4) C19 0.062(8) 0.076(9) 0.098(9) -0.023(7) -0.004(7) -0.007(6) C20 0.146(15) 0.120(13) 0.098(11) -0.021(9) -0.058(10) -0.017(11) C21 0.100(9) 0.068(8) 0.058(7) -0.020(6) 0.018(7) -0.024(7) C22 0.126(14) 0.231(21) 0.075(10) -0.025(11) 0.012(10) -0.061(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.742(8) . ? S1 C4 1.749(7) . ? S2 C3 1.701(7) . ? S2 C4 1.747(8) . ? S3 C5 1.740(8) . ? S3 C6 1.760(8) . ? S4 C5 1.754(8) . ? S4 C7 1.758(8) . ? S5 C6 1.721(8) . ? S5 C8 1.795(9) . ? S6 C7 1.744(8) . ? S6 C9 1.777(9) . ? C1 O1 1.220(9) . ? C1 N1 1.323(9) . ? C1 C2 1.487(10) . ? C2 C3 1.335(10) . ? C4 C5 1.350(10) . ? C6 C7 1.322(10) . ? C9 C8 1.431(12) . ? S7 C11 1.754(8) . ? S7 C13 1.762(7) . ? S8 C12 1.719(7) . ? S8 C13 1.754(8) . ? S9 C14 1.754(8) . ? S9 C15 1.765(9) . ? S10 C14 1.748(7) . ? S10 C16 1.750(8) . ? S11A C17A 1.63(2) . ? S11A C15 1.754(10) . ? S11B C17B 1.59(2) . ? S11B C15 1.846(14) . ? S12 C16 1.746(8) . ? S12 C18 1.759(13) . ? C10 O2 1.235(9) . ? C10 N2 1.329(9) . ? C10 C11 1.503(10) . ? C11 C12 1.325(10) . ? C13 C14 1.337(9) . ? C15 C16 1.296(12) . ? C17A C18 1.43(3) . ? C17B C18 1.40(2) . ? O3 C21 1.407(10) . ? O3 C19 1.415(11) . ? C19 C20 1.47(2) . ? C20 C22 1.50(2) . ? C21 C22 1.46 . ? O4 C24 0.95(5) 3_557 ? O4 C25 1.09(5) 3_557 ? O4 C26 1.45(4) . ? O4 C23 1.68(4) . ? O4 C23 1.82(4) 3_557 ? C23 C25 0.80(5) 3_557 ? C23 C26 0.84(4) 3_557 ? C23 C24 1.11(5) . ? C23 O4 1.82(4) 3_557 ? C24 O4 0.95(5) 3_557 ? C24 C26 1.04(5) 3_557 ? C24 C25 1.71(6) . ? C24 C25 1.78(6) 3_557 ? C25 C23 0.80(5) 3_557 ? C25 O4 1.09(5) 3_557 ? C25 C26 1.47(6) . ? C25 C24 1.78(6) 3_557 ? C26 C23 0.84(4) 3_557 ? C26 C24 1.04(5) 3_557 ? 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 C4 93.5(3) . . ? C3 S2 C4 94.8(4) . . ? C5 S3 C6 93.8(4) . . ? C5 S4 C7 93.5(4) . . ? C6 S5 C8 103.5(4) . . ? C7 S6 C9 97.6(4) . . ? O1 C1 N1 123.3(7) . . ? O1 C1 C2 118.5(7) . . ? N1 C1 C2 118.1(7) . . ? C3 C2 C1 128.2(7) . . ? C3 C2 S1 117.9(6) . . ? C1 C2 S1 113.9(6) . . ? C2 C3 S2 118.3(6) . . ? C5 C4 S2 122.4(6) . . ? C5 C4 S1 122.1(6) . . ? S2 C4 S1 115.5(4) . . ? C4 C5 S3 123.0(6) . . ? C4 C5 S4 123.0(6) . . ? S3 C5 S4 114.0(4) . . ? C7 C6 S5 127.5(6) . . ? C7 C6 S3 117.0(6) . . ? S5 C6 S3 115.4(4) . . ? C6 C7 S6 123.6(6) . . ? C6 C7 S4 117.4(6) . . ? S6 C7 S4 118.8(4) . . ? C8 C9 S6 116.6(7) . . ? C9 C8 S5 119.6(7) . . ? C11 S7 C13 94.5(4) . . ? C12 S8 C13 95.1(4) . . ? C14 S9 C15 93.8(4) . . ? C14 S10 C16 95.0(4) . . ? C17A S11A C15 108.3(10) . . ? C17B S11B C15 101.2(10) . . ? C16 S12 C18 103.6(6) . . ? O2 C10 N2 124.9(7) . . ? O2 C10 C11 120.0(7) . . ? N2 C10 C11 115.0(7) . . ? C12 C11 C10 128.7(7) . . ? C12 C11 S7 117.0(6) . . ? C10 C11 S7 114.3(6) . . ? C11 C12 S8 118.9(6) . . ? C14 C13 S8 122.5(6) . . ? C14 C13 S7 123.2(6) . . ? S8 C13 S7 114.2(4) . . ? C13 C14 S10 122.4(6) . . ? C13 C14 S9 123.0(6) . . ? S10 C14 S9 114.3(4) . . ? C16 C15 S11A 125.2(7) . . ? C16 C15 S9 118.5(7) . . ? S11A C15 S9 116.2(6) . . ? C16 C15 S11B 125.2(8) . . ? S11A C15 S11B 35.1(6) . . ? S9 C15 S11B 106.0(6) . . ? C15 C16 S12 125.0(7) . . ? C15 C16 S10 117.4(6) . . ? S12 C16 S10 117.6(5) . . ? C18 C17A S11A 124.0(19) . . ? C18 C17B S11B 133.7(16) . . ? C17B C18 C17A 39.1(11) . . ? C17B C18 S12 123.4(12) . . ? C17A C18 S12 117.9(13) . . ? C21 O3 C19 106.9(7) . . ? O3 C19 C20 109.3(10) . . ? C19 C20 C22 100.3(10) . . ? O3 C21 C22 108.1(5) . . ? C21 C22 C20 104.2(6) . . ? C24 O4 C25 113.1(42) 3_557 3_557 ? C24 O4 C26 45.8(33) 3_557 . ? C25 O4 C26 127.9(32) 3_557 . ? C24 O4 C23 101.3(34) 3_557 . ? C25 O4 C23 22.8(27) 3_557 . ? C26 O4 C23 105.4(19) . . ? C24 O4 C23 30.6(33) 3_557 3_557 ? C25 O4 C23 106.8(28) 3_557 3_557 ? C26 O4 C23 27.0(13) . 3_557 ? C23 O4 C23 87.0(15) . 3_557 ? C25 C23 C26 128.1(66) 3_557 3_557 ? C25 C23 C24 136.7(62) 3_557 . ? C26 C23 C24 62.7(37) 3_557 . ? C25 C23 O4 32.1(42) 3_557 . ? C26 C23 O4 124.9(38) 3_557 . ? C24 C23 O4 104.8(32) . . ? C25 C23 O4 120.6(49) 3_557 3_557 ? C26 C23 O4 51.3(33) 3_557 3_557 ? C24 C23 O4 25.9(28) . 3_557 ? O4 C23 O4 93.0(15) . 3_557 ? O4 C24 C26 93.2(52) 3_557 3_557 ? O4 C24 C23 123.6(55) 3_557 . ? C26 C24 C23 46.0(32) 3_557 . ? O4 C24 C25 36.0(28) 3_557 . ? C26 C24 C25 110.4(46) 3_557 . ? C23 C24 C25 113.4(39) . . ? O4 C24 C25 113.7(43) 3_557 3_557 ? C26 C24 C25 56.0(43) 3_557 3_557 ? C23 C24 C25 17.9(28) . 3_557 ? C25 C24 C25 96.6(29) . 3_557 ? C23 C25 O4 125.0(64) 3_557 3_557 ? C23 C25 C26 26.8(36) 3_557 . ? O4 C25 C26 123.8(39) 3_557 . ? C23 C25 C24 107.3(51) 3_557 . ? O4 C25 C24 30.9(24) 3_557 . ? C26 C25 C24 96.2(34) . . ? C23 C25 C24 25.4(37) 3_557 3_557 ? O4 C25 C24 99.8(36) 3_557 3_557 ? C26 C25 C24 35.9(20) . 3_557 ? C24 C25 C24 83.4(29) . 3_557 ? C23 C26 C24 71.4(38) 3_557 3_557 ? C23 C26 C25 25.2(33) 3_557 . ? C24 C26 C25 88.1(45) 3_557 . ? C23 C26 O4 101.8(39) 3_557 . ? C24 C26 O4 41.0(37) 3_557 . ? C25 C26 O4 105.6(25) . . ? _refine_diff_density_max 0.590 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.103 #===END data_AMII _audit_creation_method SHELXL _chemical_name_systematic ; 3-methylamido-3',4'ethylenedithiotetrathiafulvalene ; _chemical_name_common 'EDT-TTF(CONHMe)' _chemical_formula_moiety 'C10 H9 N O S6' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H9 N O S6' _chemical_formula_weight 351.54 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P (2)1 (2)1 (2)1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.6636(15) _cell_length_b 17.584(4) _cell_length_c 21.553(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2904.5(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 24.04 _exptl_crystal_description 'plate' _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.045 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method ? _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.927 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'area detector' _diffrn_measurement_device_type 'Stoe-IPDS' _diffrn_detector_area_resol_mean 6.66 _diffrn_measurement_method 'Oscillation, phi incr. 1.2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13914 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 24.04 _reflns_number_total 4459 _reflns_number_observed 3082 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'EXPOSE (STOE)' _computing_cell_refinement 'CELL (STOE)' _computing_data_reduction 'INTEGRATE (STOE)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP (XTAL 3.4)' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0282P)^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 0.00(9) _refine_ls_number_reflns 4459 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_obs 0.0360 _refine_ls_wR_factor_all 0.0705 _refine_ls_wR_factor_obs 0.0643 _refine_ls_goodness_of_fit_all 0.910 _refine_ls_goodness_of_fit_obs 1.017 _refine_ls_restrained_S_all 0.910 _refine_ls_restrained_S_obs 1.017 _refine_ls_shift/esd_max -0.196 _refine_ls_shift/esd_mean 0.023 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.6783(2) 0.47470(7) 0.15442(5) 0.0697(4) Uani 1 d . . S2 S 0.4171(2) 0.59497(6) 0.17666(6) 0.0717(4) Uani 1 d . . S3 S 0.1479(2) 0.51456(7) 0.08491(6) 0.0690(4) Uani 1 d . . S4 S 0.4055(2) 0.39509(8) 0.05521(6) 0.0811(4) Uani 1 d . . S5 S -0.1159(2) 0.46112(12) -0.00292(7) 0.1141(6) Uani 1 d . . S6 S 0.1805(3) 0.31662(9) -0.03518(7) 0.0985(5) Uani 1 d . . N1 N 0.9356(6) 0.5838(2) 0.2878(2) 0.0703(12) Uani 1 d . . H1 H 0.8691(6) 0.6225(2) 0.2938(2) 0.084 Uiso 1 calc R . O1 O 0.9780(5) 0.4750(2) 0.23518(13) 0.0753(10) Uani 1 d . . C1 C 1.0935(8) 0.5775(3) 0.3232(2) 0.088(2) Uani 1 d . . H1A H 1.1143(26) 0.6243(7) 0.3449(13) 0.133 Uiso 1 calc R . H1B H 1.1895(10) 0.5673(20) 0.2958(3) 0.133 Uiso 1 calc R . H1C H 1.0824(19) 0.5368(13) 0.3525(11) 0.133 Uiso 1 calc R . C2 C 0.8875(7) 0.5315(2) 0.2454(2) 0.0588(12) Uani 1 d . . C3 C 0.7209(7) 0.5420(2) 0.2120(2) 0.0535(12) Uani 1 d . . C4 C 0.6027(7) 0.5951(2) 0.2210(2) 0.0621(13) Uani 1 d . . H4 H 0.6197(7) 0.6324(2) 0.2511(2) 0.074 Uiso 1 calc R . C5 C 0.4691(6) 0.5104(2) 0.1373(2) 0.0552(12) Uani 1 d . . C6 C 0.3576(6) 0.4775(3) 0.0983(2) 0.0593(12) Uani 1 d . . C7 C 0.0906(7) 0.4464(3) 0.0292(2) 0.0683(14) Uani 1 d . . C8 C 0.2048(7) 0.3922(3) 0.0167(2) 0.0630(13) Uani 1 d . . C9A C -0.0881(54) 0.4073(15) -0.0702(14) 0.119(10) Uani 0.50 d P . H9A H -0.1989(54) 0.4052(15) -0.0918(14) 0.143 Uiso 0.50 calc PR . H9B H -0.0060(54) 0.4335(15) -0.0969(14) 0.143 Uiso 0.50 calc PR . C9B C -0.1485(39) 0.3836(25) -0.0577(13) 0.124(14) Uani 0.50 d P . H9C H -0.1961(39) 0.3398(25) -0.0362(13) 0.148 Uiso 0.50 calc PR . H9D H -0.2311(39) 0.3990(25) -0.0894(13) 0.148 Uiso 0.50 calc PR . C10A C -0.0236(43) 0.3266(11) -0.0608(14) 0.109(7) Uani 0.50 d P . H10A H -0.0336(43) 0.3000(11) -0.1000(14) 0.131 Uiso 0.50 calc PR . H10B H -0.1011(43) 0.3016(11) -0.0316(14) 0.131 Uiso 0.50 calc PR . C10B C 0.0185(32) 0.3634(20) -0.0865(8) 0.106(6) Uani 0.50 d P . H10C H 0.0706(32) 0.4094(20) -0.1031(8) 0.127 Uiso 0.50 calc PR . H10D H -0.0048(32) 0.3298(20) -0.1213(8) 0.127 Uiso 0.50 calc PR . S7 S 0.5480(2) 0.28223(6) 0.24655(6) 0.0646(3) Uani 1 d . . S8 S 0.4955(2) 0.42495(7) 0.31649(6) 0.0771(4) Uani 1 d . . S9 S 0.9110(2) 0.25297(7) 0.32276(6) 0.0782(4) Uani 1 d . . S10 S 0.8587(2) 0.39812(8) 0.38842(7) 0.0995(5) Uani 1 d . . S11 S 1.2098(3) 0.20671(11) 0.39773(9) 0.1259(7) Uani 1 d . . S12 S 1.1536(2) 0.38046(10) 0.47244(7) 0.0986(5) Uani 1 d . . O2 O 0.2508(4) 0.2250(2) 0.17975(12) 0.0602(8) Uani 1 d . . N2 N 0.0837(5) 0.3300(2) 0.17741(15) 0.0586(9) Uani 1 d . . H2 H 0.0709(5) 0.3763(2) 0.18938(15) 0.070 Uiso 1 calc R . C11 C -0.0455(7) 0.2967(3) 0.1372(2) 0.0683(13) Uani 1 d . . H11A H -0.1109(25) 0.3363(3) 0.1173(10) 0.102 Uiso 1 calc R . H11B H -0.1231(23) 0.2655(13) 0.1612(3) 0.102 Uiso 1 calc R . H11C H 0.0112(7) 0.2660(13) 0.1064(8) 0.102 Uiso 1 calc R . C12 C 0.2213(6) 0.2913(3) 0.1963(2) 0.0533(12) Uani 1 d . . C13 C 0.3479(6) 0.3299(2) 0.2381(2) 0.0535(11) Uani 1 d . . C14 C 0.3282(7) 0.3942(3) 0.2696(2) 0.0634(13) Uani 1 d . . H14 H 0.2255(7) 0.4221(3) 0.2664(2) 0.076 Uiso 1 calc R . C15 C 0.6291(7) 0.3456(2) 0.3030(2) 0.0600(12) Uani 1 d . . C16 C 0.7779(7) 0.3335(2) 0.3332(2) 0.0651(13) Uani 1 d . . C17 C 1.0496(7) 0.2742(3) 0.3840(2) 0.0682(14) Uani 1 d . . C18 C 1.0292(7) 0.3401(3) 0.4129(2) 0.0688(14) Uani 1 d . . C19A C 1.3237(34) 0.2493(16) 0.4574(10) 0.136(8) Uani 0.50 d P . H19A H 1.2886(34) 0.2218(16) 0.4944(10) 0.163 Uiso 0.50 calc PR . H19B H 1.4446(34) 0.2355(16) 0.4502(10) 0.163 Uiso 0.50 calc PR . C19B C 1.3756(21) 0.2656(12) 0.4253(7) 0.085(5) Uani 0.50 d P . H19C H 1.4758(21) 0.2341(12) 0.4351(7) 0.102 Uiso 0.50 calc PR . H19D H 1.4098(21) 0.2997(12) 0.3921(7) 0.102 Uiso 0.50 calc PR . C20A C 1.3290(45) 0.3248(26) 0.4754(17) 0.151(18) Uani 0.50 d P . H20A H 1.4184(45) 0.3492(26) 0.4505(17) 0.181 Uiso 0.50 calc PR . H20B H 1.3701(45) 0.3257(26) 0.5180(17) 0.181 Uiso 0.50 calc PR . C20B C 1.3339(45) 0.3119(31) 0.4804(17) 0.136(14) Uani 0.50 d P . H20C H 1.4380(45) 0.3397(31) 0.4922(17) 0.164 Uiso 0.50 calc PR . H20D H 1.3060(45) 0.2776(31) 0.5143(17) 0.164 Uiso 0.50 calc PR . 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 0.0621(9) 0.0649(8) 0.0820(8) -0.0247(6) -0.0124(7) 0.0129(7) S2 0.0624(9) 0.0565(7) 0.0963(9) -0.0179(7) -0.0122(7) 0.0099(6) S3 0.0568(10) 0.0667(8) 0.0835(8) -0.0091(6) -0.0051(6) 0.0027(7) S4 0.0653(10) 0.0779(9) 0.1000(9) -0.0330(7) -0.0106(7) 0.0077(8) S5 0.0776(14) 0.155(2) 0.1099(11) -0.0305(11) -0.0346(9) 0.0166(12) S6 0.1099(15) 0.0966(11) 0.0889(10) -0.0360(8) -0.0053(9) -0.0122(10) N1 0.070(3) 0.055(3) 0.086(3) -0.020(2) -0.017(2) 0.012(2) O1 0.074(3) 0.064(2) 0.087(2) -0.023(2) -0.020(2) 0.022(2) C1 0.079(4) 0.079(4) 0.108(4) -0.025(3) -0.036(3) 0.006(3) C2 0.067(4) 0.045(3) 0.064(3) -0.001(2) 0.002(2) 0.007(3) C3 0.059(4) 0.041(3) 0.061(2) 0.001(2) -0.003(2) 0.009(2) C4 0.068(4) 0.042(3) 0.076(3) -0.010(2) -0.007(2) -0.004(3) C5 0.056(4) 0.052(3) 0.057(2) -0.003(2) 0.002(2) -0.004(2) C6 0.054(3) 0.055(3) 0.069(3) -0.002(2) 0.002(2) -0.002(2) C7 0.066(4) 0.080(4) 0.059(3) 0.005(2) -0.010(3) -0.008(3) C8 0.059(4) 0.072(3) 0.058(3) 0.004(2) 0.006(2) -0.013(3) C9A 0.113(25) 0.113(18) 0.131(17) 0.030(13) -0.070(17) -0.015(17) C9B 0.083(18) 0.188(31) 0.100(12) -0.077(15) 0.000(11) -0.071(18) C10A 0.120(19) 0.110(15) 0.097(13) 0.012(10) -0.056(13) -0.013(14) C10B 0.125(19) 0.132(21) 0.060(9) 0.000(10) -0.025(11) -0.029(15) S7 0.0573(9) 0.0540(7) 0.0826(8) -0.0071(6) -0.0066(7) 0.0027(6) S8 0.0830(11) 0.0516(7) 0.0967(9) -0.0095(7) -0.0261(8) 0.0039(7) S9 0.0651(11) 0.0719(8) 0.0976(9) -0.0144(7) -0.0137(7) 0.0033(7) S10 0.0983(14) 0.0639(9) 0.1363(11) -0.0217(8) -0.0523(10) 0.0154(9) S11 0.104(2) 0.1226(14) 0.1507(15) -0.0506(12) -0.0429(12) 0.0587(13) S12 0.0890(14) 0.1108(13) 0.0959(9) -0.0291(9) -0.0302(9) 0.0172(10) O2 0.067(2) 0.043(2) 0.071(2) -0.0039(14) 0.002(2) 0.0062(15) N2 0.067(3) 0.043(2) 0.066(2) -0.005(2) -0.011(2) 0.005(2) C11 0.068(4) 0.064(3) 0.073(3) -0.004(2) -0.004(3) -0.003(3) C12 0.065(4) 0.049(3) 0.046(2) 0.007(2) 0.005(2) 0.004(3) C13 0.057(3) 0.048(3) 0.055(2) 0.007(2) -0.003(2) 0.002(2) C14 0.072(4) 0.047(3) 0.071(3) -0.001(2) -0.006(2) 0.009(3) C15 0.060(4) 0.048(3) 0.072(3) 0.010(2) -0.001(3) -0.001(2) C16 0.060(4) 0.060(3) 0.075(3) 0.010(2) -0.011(3) 0.000(3) C17 0.065(4) 0.079(4) 0.061(3) 0.001(3) 0.000(2) 0.011(3) C18 0.056(4) 0.084(4) 0.066(3) 0.002(3) 0.007(2) 0.003(3) C19A 0.096(20) 0.171(23) 0.141(21) 0.016(17) -0.018(14) 0.059(19) C19B 0.041(9) 0.114(13) 0.101(12) -0.003(10) 0.007(8) 0.013(8) C20A 0.125(26) 0.127(26) 0.199(27) -0.059(18) -0.124(22) 0.025(18) C20B 0.092(21) 0.128(24) 0.190(28) -0.046(19) -0.013(17) 0.065(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 C3 1.746(4) . ? S1 C5 1.760(5) . ? S2 C4 1.714(5) . ? S2 C5 1.758(4) . ? S3 C7 1.753(5) . ? S3 C6 1.759(5) . ? S4 C8 1.748(5) . ? S4 C6 1.760(5) . ? S5 C9A 1.74(4) . ? S5 C7 1.746(5) . ? S5 C9B 1.82(3) . ? S6 C10A 1.67(2) . ? S6 C8 1.747(5) . ? S6 C10B 1.86(3) . ? N1 C2 1.347(5) . ? N1 C1 1.435(6) . ? N1 H1 0.86 . ? O1 C2 1.231(5) . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C2 C3 1.477(6) . ? C3 C4 1.316(6) . ? C4 H4 0.93 . ? C5 C6 1.331(6) . ? C7 C8 1.322(6) . ? C9A C10A 1.51(4) . ? C9A H9A 0.97 . ? C9A H9B 0.97 . ? C9B C10B 1.47(5) . ? C9B H9C 0.97 . ? C9B H9D 0.97 . ? C10A H10A 0.97 . ? C10A H10B 0.97 . ? C10B H10C 0.97 . ? C10B H10D 0.97 . ? S7 C13 1.757(5) . ? S7 C15 1.762(5) . ? S8 C14 1.720(5) . ? S8 C15 1.756(5) . ? S9 C17 1.735(5) . ? S9 C16 1.760(5) . ? S10 C18 1.740(5) . ? S10 C16 1.757(5) . ? S11 C19A 1.72(3) . ? S11 C17 1.733(5) . ? S11 C19B 1.74(2) . ? S12 C20A 1.66(4) . ? S12 C18 1.750(5) . ? S12 C20B 1.84(4) . ? O2 C12 1.241(5) . ? N2 C12 1.319(5) . ? N2 C11 1.440(5) . ? N2 H2 0.86 . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? C12 C13 1.486(6) . ? C13 C14 1.328(6) . ? C14 H14 0.93 . ? C15 C16 1.331(6) . ? C17 C18 1.324(7) . ? C19A C20A 1.38(5) . ? C19A H19A 0.97 . ? C19A H19B 0.97 . ? C19B C20B 1.47(4) . ? C19B H19C 0.97 . ? C19B H19D 0.97 . ? C20A H20A 0.97 . ? C20A H20B 0.97 . ? C20B H20C 0.97 . ? C20B H20D 0.97 . ? 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 S1 C5 94.5(2) . . ? C4 S2 C5 94.7(2) . . ? C7 S3 C6 95.0(2) . . ? C8 S4 C6 95.3(2) . . ? C9A S5 C7 97.9(12) . . ? C9A S5 C9B 21.8(11) . . ? C7 S5 C9B 105.7(14) . . ? C10A S6 C8 103.4(10) . . ? C10A S6 C10B 29.3(8) . . ? C8 S6 C10B 96.7(9) . . ? C2 N1 C1 122.6(4) . . ? C2 N1 H1 118.7(3) . . ? C1 N1 H1 118.7(2) . . ? N1 C1 H1A 109.5(2) . . ? N1 C1 H1B 109.5(3) . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5(3) . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 N1 121.2(4) . . ? O1 C2 C3 120.1(4) . . ? N1 C2 C3 118.8(4) . . ? C4 C3 C2 127.7(4) . . ? C4 C3 S1 117.2(4) . . ? C2 C3 S1 115.1(3) . . ? C3 C4 S2 119.2(3) . . ? C3 C4 H4 120.4(3) . . ? S2 C4 H4 120.4(2) . . ? C6 C5 S2 121.8(4) . . ? C6 C5 S1 124.2(3) . . ? S2 C5 S1 114.0(2) . . ? C5 C6 S3 122.0(3) . . ? C5 C6 S4 123.9(4) . . ? S3 C6 S4 114.1(3) . . ? C8 C7 S5 128.8(4) . . ? C8 C7 S3 117.8(4) . . ? S5 C7 S3 113.4(3) . . ? C7 C8 S6 127.5(4) . . ? C7 C8 S4 117.7(4) . . ? S6 C8 S4 114.8(3) . . ? C10A C9A S5 116.0(20) . . ? C10A C9A H9A 108.1(14) . . ? S5 C9A H9A 108.2(12) . . ? C10A C9A H9B 108.6(30) . . ? S5 C9A H9B 108.3(11) . . ? H9A C9A H9B 107.4 . . ? C10B C9B S5 109.7(14) . . ? C10B C9B H9C 109.4(29) . . ? S5 C9B H9C 109.6(11) . . ? C10B C9B H9D 110.1(21) . . ? S5 C9B H9D 109.9(16) . . ? H9C C9B H9D 108.2 . . ? C9A C10A S6 116.7(20) . . ? C9A C10A H10A 108.1(16) . . ? S6 C10A H10A 108.0(12) . . ? C9A C10A H10B 108.3(30) . . ? S6 C10A H10B 108.2(12) . . ? H10A C10A H10B 107.3 . . ? C9B C10B S6 116.0(25) . . ? C9B C10B H10C 108.0(28) . . ? S6 C10B H10C 108.4(8) . . ? C9B C10B H10D 108.3(10) . . ? S6 C10B H10D 108.4(8) . . ? H10C C10B H10D 107.4 . . ? C13 S7 C15 94.5(2) . . ? C14 S8 C15 95.0(2) . . ? C17 S9 C16 94.8(2) . . ? C18 S10 C16 95.2(3) . . ? C19A S11 C17 100.9(9) . . ? C19A S11 C19B 28.3(7) . . ? C17 S11 C19B 99.7(7) . . ? C20A S12 C18 103.3(10) . . ? C20A S12 C20B 6.0(32) . . ? C18 S12 C20B 102.2(12) . . ? C12 N2 C11 121.8(4) . . ? C12 N2 H2 119.1(2) . . ? C11 N2 H2 119.1(2) . . ? N2 C11 H11A 109.5(2) . . ? N2 C11 H11B 109.5(2) . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5(2) . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 N2 122.7(4) . . ? O2 C12 C13 118.9(4) . . ? N2 C12 C13 118.3(4) . . ? C14 C13 C12 128.6(4) . . ? C14 C13 S7 116.9(4) . . ? C12 C13 S7 114.6(3) . . ? C13 C14 S8 118.9(4) . . ? C13 C14 H14 120.5(3) . . ? S8 C14 H14 120.5(2) . . ? C16 C15 S8 123.0(4) . . ? C16 C15 S7 122.7(4) . . ? S8 C15 S7 114.3(3) . . ? C15 C16 S10 122.1(4) . . ? C15 C16 S9 124.2(4) . . ? S10 C16 S9 113.8(3) . . ? C18 C17 S9 118.2(4) . . ? C18 C17 S11 127.1(4) . . ? S9 C17 S11 114.6(3) . . ? C17 C18 S12 129.5(4) . . ? C17 C18 S10 117.4(4) . . ? S12 C18 S10 113.1(3) . . ? C20A C19A S11 129.8(20) . . ? C20A C19A H19A 104.7(22) . . ? S11 C19A H19A 104.8(8) . . ? C20A C19A H19B 104.9(20) . . ? S11 C19A H19B 104.8(9) . . ? H19A C19A H19B 105.8 . . ? C20B C19B S11 116.4(20) . . ? C20B C19B H19C 108.2(16) . . ? S11 C19B H19C 108.2(6) . . ? C20B C19B H19D 108.2(23) . . ? S11 C19B H19D 108.2(5) . . ? H19C C19B H19D 107.3 . . ? C19A C20A S12 122.0(21) . . ? C19A C20A H20A 106.8(22) . . ? S12 C20A H20A 106.8(17) . . ? C19A C20A H20B 107.0(17) . . ? S12 C20A H20B 106.8(11) . . ? H20A C20A H20B 106.7 . . ? C19B C20B S12 116.6(23) . . ? C19B C20B H20C 108.1(17) . . ? S12 C20B H20C 108.1(15) . . ? C19B C20B H20D 108.2(23) . . ? S12 C20B H20D 108.2(15) . . ? H20C C20B H20D 107.3 . . ? _refine_diff_density_max 0.264 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.042 #===END data_AMIII _audit_creation_method SHELXL _chemical_name_systematic ; 3-dimethylamido-3',4'-ethylenedithiotetrathiafulvalene ; _chemical_name_common 'EDT-TTF-CONMe2' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H11 N O S6' _chemical_formula_weight 365.57 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 2(1) 2(1) 2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.2990(13) _cell_length_b 7.886(2) _cell_length_c 29.631(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1471.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.07 _cell_measurement_theta_max 14.5 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method ? _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.918 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius Mach3' _diffrn_measurement_method 'Omega-2 Theta' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3802 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.1958 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.96 _reflns_number_total 2845 _reflns_number_observed 1369 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 EXPRESS' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4 (Harms, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP (XTAL 3.4)' _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 13 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0840P)^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 0.71(27) _refine_ls_number_reflns 2832 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1987 _refine_ls_R_factor_obs 0.0470 _refine_ls_wR_factor_all 0.1998 _refine_ls_wR_factor_obs 0.1092 _refine_ls_goodness_of_fit_all 0.921 _refine_ls_goodness_of_fit_obs 0.936 _refine_ls_restrained_S_all 1.154 _refine_ls_restrained_S_obs 0.936 _refine_ls_shift/esd_max -0.354 _refine_ls_shift/esd_mean 0.050 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.1320(3) 0.5108(3) 0.08879(9) 0.0525(6) Uani 1 d . . S2 S 0.5730(3) 0.4679(3) 0.11974(9) 0.0605(7) Uani 1 d . . S3 S 0.0066(3) 0.1552(3) 0.13761(9) 0.0618(8) Uani 1 d . . S4 S 0.4442(3) 0.1234(3) 0.17161(9) 0.0540(6) Uani 1 d . . S5 S -0.1437(3) -0.1649(3) 0.17538(10) 0.0586(7) Uani 1 d . . S6 S 0.3658(4) -0.1950(4) 0.22055(12) 0.0873(11) Uani 1 d . . O1 O 0.0107(10) 0.7901(7) 0.0435(2) 0.072(2) Uani 1 d . . N1 N 0.3000(11) 0.9555(9) 0.0395(2) 0.051(2) Uani 1 d . . C1 C 0.1761(18) 1.0814(12) 0.0141(4) 0.077(3) Uani 1 d . . H1A H 0.2171(82) 1.0785(63) -0.0171(6) 0.116 Uiso 1 calc R . H1B H 0.2026(85) 1.1924(16) 0.0262(16) 0.116 Uiso 1 calc R . H1C H 0.0276(19) 1.0556(52) 0.0167(19) 0.116 Uiso 1 calc R . C2 C 0.5225(16) 0.9927(12) 0.0469(4) 0.075(3) Uani 1 d . . H2A H 0.5620(34) 1.0907(61) 0.0296(21) 0.112 Uiso 1 calc R . H2B H 0.6067(17) 0.8974(41) 0.0376(24) 0.112 Uiso 1 calc R . H2C H 0.5462(26) 1.0146(93) 0.0783(6) 0.112 Uiso 1 calc R . C3 C 0.2016(15) 0.8124(11) 0.0515(3) 0.052(2) Uani 1 d . . C4 C 0.3136(11) 0.6742(10) 0.0766(3) 0.040(2) Uani 1 d . . C5 C 0.5106(12) 0.6510(10) 0.0894(3) 0.049(2) Uani 1 d . . H5 H 0.6149(12) 0.7303(10) 0.0824(3) 0.059 Uiso 1 calc R . C6 C 0.3145(11) 0.3847(10) 0.1190(3) 0.041(2) Uani 1 d . . C7 C 0.2628(11) 0.2414(10) 0.1398(3) 0.038(2) Uani 1 d . . C8 C 0.0692(12) -0.0258(8) 0.1683(3) 0.038(2) Uani 1 d . . C9 C 0.2673(12) -0.0400(10) 0.1844(3) 0.042(2) Uani 1 d . . C10A C -0.0465(71) -0.3045(69) 0.2226(12) 0.092(16) Uani 0.50 d P . H10A H -0.1487(71) -0.2961(69) 0.2470(12) 0.111 Uiso 0.50 calc PR . H10B H -0.0508(71) -0.4206(69) 0.2118(12) 0.111 Uiso 0.50 calc PR . C10B C -0.0318(76) -0.3278(54) 0.2030(10) 0.063(11) Uani 0.50 d P . H10C H -0.1236(76) -0.3461(54) 0.2288(10) 0.075 Uiso 0.50 calc PR . H10D H -0.0543(76) -0.4246(54) 0.1834(10) 0.075 Uiso 0.50 calc PR . C11A C 0.1301(44) -0.2809(26) 0.2389(7) 0.042(5) Uani 0.50 d P . H11A H 0.1712(44) -0.3929(26) 0.2493(7) 0.051 Uiso 0.50 calc PR . H11B H 0.0999(44) -0.2171(26) 0.2662(7) 0.051 Uiso 0.50 calc PR . C11B C 0.1600(49) -0.3493(28) 0.2189(10) 0.069(7) Uani 0.50 d P . H11C H 0.2183(49) -0.4449(28) 0.2024(10) 0.082 Uiso 0.50 calc PR . H11D H 0.1418(49) -0.3872(28) 0.2498(10) 0.082 Uiso 0.50 calc PR . 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 0.0359(11) 0.0408(13) 0.081(2) 0.0169(12) -0.0073(11) -0.0019(10) S2 0.0375(11) 0.0504(14) 0.094(2) 0.0293(14) -0.0129(13) -0.0093(11) S3 0.0380(11) 0.0537(14) 0.094(2) 0.0345(14) -0.0126(12) -0.0096(11) S4 0.0367(11) 0.0535(13) 0.072(2) 0.0271(12) -0.0133(12) -0.0091(10) S5 0.0418(11) 0.0445(13) 0.090(2) 0.0179(13) -0.0058(13) -0.0095(10) S6 0.0446(13) 0.086(2) 0.131(3) 0.073(2) -0.005(2) -0.0011(14) O1 0.057(4) 0.053(4) 0.105(6) 0.024(4) -0.026(4) -0.006(3) N1 0.062(5) 0.035(4) 0.057(5) 0.010(4) 0.010(4) 0.002(4) C1 0.112(9) 0.049(6) 0.071(9) 0.028(5) -0.007(6) 0.009(6) C2 0.086(7) 0.050(6) 0.088(8) 0.023(5) 0.006(6) -0.025(6) C3 0.058(6) 0.037(5) 0.062(7) 0.002(5) -0.004(5) 0.010(5) C4 0.039(4) 0.027(4) 0.053(6) 0.008(4) 0.005(4) -0.003(4) C5 0.037(4) 0.044(5) 0.068(6) 0.021(5) -0.009(4) -0.018(4) C6 0.037(4) 0.038(5) 0.047(6) -0.003(4) 0.004(4) 0.000(4) C7 0.030(4) 0.038(4) 0.047(6) 0.013(4) -0.001(4) -0.002(3) C8 0.040(4) 0.031(4) 0.044(5) -0.001(4) 0.013(4) 0.002(4) C9 0.036(4) 0.049(5) 0.041(5) 0.015(4) 0.002(4) 0.002(4) C10A 0.051(18) 0.140(34) 0.086(32) 0.093(29) 0.016(24) 0.008(19) C10B 0.074(23) 0.061(14) 0.054(22) 0.045(16) -0.025(19) -0.040(15) C11A 0.068(15) 0.032(12) 0.027(13) 0.010(8) -0.013(12) 0.001(12) C11B 0.094(21) 0.040(14) 0.072(20) -0.003(12) -0.002(19) -0.012(15) _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 C6 1.764(8) . ? S1 C4 1.760(7) . ? S2 C5 1.746(8) . ? S2 C6 1.756(7) . ? S3 C7 1.752(7) . ? S3 C8 1.738(8) . ? S4 C9 1.746(8) . ? S4 C7 1.750(8) . ? S5 C10B 1.68(4) . ? S5 C8 1.745(7) . ? S5 C10A 1.88(4) . ? S6 C11A 1.72(3) . ? S6 C9 1.739(8) . ? S6 C11B 1.78(3) . ? O1 C3 1.238(10) . ? N1 C3 1.335(10) . ? N1 C2 1.449(11) . ? N1 C1 1.470(11) . ? C3 C4 1.496(11) . ? C4 C5 1.311(10) . ? C6 C7 1.327(10) . ? C8 C9 1.340(11) . ? C10A C11A 1.23(5) . ? C10B C11B 1.31(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 C6 S1 C4 95.4(4) . . ? C5 S2 C6 95.4(4) . . ? C7 S3 C8 95.2(4) . . ? C9 S4 C7 95.3(4) . . ? C10B S5 C8 102.5(14) . . ? C10B S5 C10A 18.8(24) . . ? C8 S5 C10A 101.9(14) . . ? C11A S6 C9 99.4(8) . . ? C11A S6 C11B 27.2(8) . . ? C9 S6 C11B 101.7(10) . . ? C3 N1 C2 125.5(8) . . ? C3 N1 C1 117.4(8) . . ? C2 N1 C1 117.0(8) . . ? O1 C3 N1 121.3(8) . . ? O1 C3 C4 116.7(8) . . ? N1 C3 C4 121.9(8) . . ? C5 C4 C3 133.8(8) . . ? C5 C4 S1 117.0(6) . . ? C3 C4 S1 109.2(6) . . ? C4 C5 S2 118.5(6) . . ? C7 C6 S1 123.8(6) . . ? C7 C6 S2 122.7(6) . . ? S1 C6 S2 113.6(5) . . ? C6 C7 S3 122.6(6) . . ? C6 C7 S4 122.8(6) . . ? S3 C7 S4 114.5(4) . . ? C9 C8 S5 128.3(6) . . ? C9 C8 S3 117.8(6) . . ? S5 C8 S3 113.8(4) . . ? C8 C9 S4 117.1(6) . . ? C8 C9 S6 127.6(6) . . ? S4 C9 S6 115.1(4) . . ? C11A C10A S5 120.0(30) . . ? C11B C10B S5 131.5(28) . . ? C10A C11A S6 135.8(21) . . ? C10B C11B S6 126.5(24) . . ? _refine_diff_density_max 0.351 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.091