Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _audit_creation_method 'SHELXL and manual editing' # SUBMISSION DETAILS _publ_contact_author ; Prof. J. D. Wallis ; _publ_contact_author_email john.wallis@ntu.ac.uk _publ_contact_author_fax 0115-948-6636 _publ_contact_author_phone 0115-848-3149 _publ_section_title ; Synthesis of Bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) Derivatives Functionalised with Two, Four or Eight Hydroxyl Groups. ; loop_ _publ_author_name _publ_author_address 'Jon-Paul Griffiths' ; School of Biomedical and Natural Sciences Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; 'R. James Brown' ; School of Biomedical and Natural Sciences Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; 'Andrew C. Brooks' ; School of Biomedical and Natural Sciences Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; 'Bertrand Vital' ; School of Biomedical and Natural Sciences Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; P.Day ; Davy-Faraday Research Laboratory The Royal Institution of Great Britain 21 Albemarle St London W1S 4BS, UK. ; 'John D. Wallis' ; School of Biomedical and Natural Sciences Nottingham Trent University Clifton Lane Nottingham UK NG11 8NS ; # TEXT _publ_section_references ; Blessing, R.H. (1995). Acta Cryst., A51, 33-38. Hooft, R. (1998). Data Collection Software, Nonius B.V., Delft, The Netherlands. Johnson, C.K., Burnett, M.N. (1996). ORTEPIII Report ORNL-6895, Oak Ridge National Laboratory, Tennessee, USA Otwinowski, M., Minor W. (1997). Methods in Enzymology 276: macromolecular crystallography A, ed. Carter, C.W. Jr, Sweet, R.M., Academic Press, 307-326. Sheldrick, G.M. (1990). Acta Cryst. A46, 467-473. Sheldrick, G.M. (1997). SHELXL-97 Program for the Refinement of Crystal Structures, University of G\"ottingen, Germany. ; _publ_section_exptl_refinement ; The structures were solved using direct methods and refined with the full-matrix least-squares technique. All non-hydrogen atoms were refined with anisotropic displacement parameters, all hydrogen atoms were located in diffence fourier maps and their positions and isotropic displacement parameters refined unless otherwise stated. ; _publ_contact_author_name 'Prof. J. D. Wallis' # DATA data_minorthione _database_code_depnum_ccdc_archive 'CCDC 230196' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5S,6S-5,6-bis((4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl)-5,6-dihydro-1,3- dithiolo[4,5-b]1,4-dithiin-2-thione ; _chemical_name_common ; 5S,6S-5,6-bis((4'R)-2',2'-dimethyl-1,3-dioxolan-4'-yl)-5,6- dihydro-1,3-dithiolo(4,5-b)1,4-dithiin-2-thione ; _chemical_melting_point 369-371 _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 O4 S5' _chemical_formula_weight 424.61 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 orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.3614(7) _cell_length_b 10.3321(4) _cell_length_c 20.0889(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1943.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12408 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.612 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R. H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12408 _diffrn_reflns_av_R_equivalents 0.1078 _diffrn_reflns_av_sigmaI/netI 0.1712 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4282 _reflns_number_gt 2239 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_cell_refinement ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_data_reduction ; 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Johnson and Burnett, 1996)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0436P)^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 0.07(12) _refine_ls_number_reflns 4282 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1543 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1153 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 0.870 _refine_ls_restrained_S_all 0.870 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration syn 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 0.86627(15) 0.94305(12) 0.20255(9) 0.0522(5) Uani 1 1 d . . . S2 S 0.68578(15) 0.71312(11) 0.17263(7) 0.0387(4) Uani 1 1 d . . . S3 S 0.83493(17) 0.72611(12) 0.29835(8) 0.0497(4) Uani 1 1 d . . . S4 S 0.53795(14) 0.46012(12) 0.20908(7) 0.0360(3) Uani 1 1 d . . . S5 S 0.70596(17) 0.47145(13) 0.34638(7) 0.0451(4) Uani 1 1 d . . . O1 O 0.8086(4) 0.3562(3) 0.14198(16) 0.0313(8) Uani 1 1 d . . . O2 O 0.6661(4) 0.2875(5) 0.05951(18) 0.0693(14) Uani 1 1 d . . . O3 O 0.6601(3) 0.1829(3) 0.36383(16) 0.0325(9) Uani 1 1 d . . . O4 O 0.8280(4) 0.2080(3) 0.44271(16) 0.0447(10) Uani 1 1 d . . . C1 C 0.7973(6) 0.8027(4) 0.2242(3) 0.0377(13) Uani 1 1 d . . . C2 C 0.6537(5) 0.5880(4) 0.2288(3) 0.0330(13) Uani 1 1 d . . . C3 C 0.7203(6) 0.5945(4) 0.2869(3) 0.0362(13) Uani 1 1 d . . . C4 C 0.6464(5) 0.3192(4) 0.2332(2) 0.0263(12) Uani 1 1 d . . . H4 H 0.5786 0.2519 0.2500 0.032 Uiso 1 1 calc R . . C5 C 0.7560(5) 0.3428(4) 0.2886(3) 0.0284(12) Uani 1 1 d . . . H5 H 0.8474 0.3692 0.2668 0.034 Uiso 1 1 calc R . . C6 C 0.7207(5) 0.2618(4) 0.1720(2) 0.0310(12) Uani 1 1 d . . . H6 H 0.7810 0.1868 0.1862 0.037 Uiso 1 1 calc R . . C7 C 0.6177(6) 0.2172(5) 0.1158(3) 0.0433(15) Uani 1 1 d . . . H7A H 0.6250 0.1227 0.1083 0.052 Uiso 1 1 calc R . . H7B H 0.5174 0.2393 0.1266 0.052 Uiso 1 1 calc R . . C8 C 0.8065(6) 0.3328(6) 0.0723(3) 0.0480(16) Uani 1 1 d . . . C9 C 0.8255(7) 0.4602(7) 0.0362(3) 0.0683(19) Uani 1 1 d . . . H9A H 0.9222 0.4931 0.0439 0.102 Uiso 0.50 1 calc PR . . H9B H 0.7555 0.5229 0.0528 0.102 Uiso 0.50 1 calc PR . . H9C H 0.8109 0.4469 -0.0117 0.102 Uiso 0.50 1 calc PR . . H9D H 0.7369 0.4822 0.0128 0.102 Uiso 0.50 1 calc PR . . H9E H 0.9036 0.4524 0.0039 0.102 Uiso 0.50 1 calc PR . . H9F H 0.8482 0.5283 0.0684 0.102 Uiso 0.50 1 calc PR . . C10 C 0.9177(7) 0.2302(6) 0.0543(3) 0.064(2) Uani 1 1 d . . . H10A H 1.0136 0.2640 0.0633 0.096 Uiso 0.50 1 calc PR . . H10B H 0.9093 0.2085 0.0070 0.096 Uiso 0.50 1 calc PR . . H10C H 0.9015 0.1524 0.0812 0.096 Uiso 0.50 1 calc PR . . H10D H 0.8693 0.1526 0.0377 0.096 Uiso 0.50 1 calc PR . . H10E H 0.9737 0.2081 0.0939 0.096 Uiso 0.50 1 calc PR . . H10F H 0.9814 0.2642 0.0198 0.096 Uiso 0.50 1 calc PR . . C11 C 0.7858(5) 0.2180(5) 0.3279(2) 0.0310(12) Uani 1 1 d . . . H11 H 0.8120 0.1469 0.2964 0.037 Uiso 1 1 calc R . . C12 C 0.9000(5) 0.2297(6) 0.3818(3) 0.0444(15) Uani 1 1 d . . . H12A H 0.9760 0.1643 0.3751 0.053 Uiso 1 1 calc R . . H12B H 0.9437 0.3169 0.3812 0.053 Uiso 1 1 calc R . . C13 C 0.7051(6) 0.1325(5) 0.4267(3) 0.0344(13) Uani 1 1 d . . . C14 C 0.7456(6) -0.0099(5) 0.4202(3) 0.0456(15) Uani 1 1 d . . . H14A H 0.6603 -0.0608 0.4098 0.068 Uiso 0.50 1 calc PR . . H14B H 0.7867 -0.0402 0.4623 0.068 Uiso 0.50 1 calc PR . . H14C H 0.8160 -0.0201 0.3845 0.068 Uiso 0.50 1 calc PR . . H14D H 0.8484 -0.0199 0.4279 0.068 Uiso 0.50 1 calc PR . . H14E H 0.7219 -0.0405 0.3754 0.068 Uiso 0.50 1 calc PR . . H14F H 0.6927 -0.0607 0.4532 0.068 Uiso 0.50 1 calc PR . . C15 C 0.5923(7) 0.1580(6) 0.4777(3) 0.0623(19) Uani 1 1 d . . . H15A H 0.5070 0.1068 0.4673 0.094 Uiso 0.50 1 calc PR . . H15B H 0.5677 0.2502 0.4775 0.094 Uiso 0.50 1 calc PR . . H15C H 0.6281 0.1338 0.5218 0.094 Uiso 0.50 1 calc PR . . H15D H 0.6282 0.2204 0.5104 0.094 Uiso 0.50 1 calc PR . . H15E H 0.5675 0.0770 0.5003 0.094 Uiso 0.50 1 calc PR . . H15F H 0.5072 0.1934 0.4559 0.094 Uiso 0.50 1 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 0.0395(9) 0.0263(7) 0.0906(13) -0.0009(8) 0.0133(9) 0.0028(6) S2 0.0329(8) 0.0291(7) 0.0543(9) 0.0063(6) 0.0032(7) 0.0023(6) S3 0.0636(11) 0.0318(7) 0.0536(10) -0.0120(7) -0.0017(9) -0.0046(7) S4 0.0255(7) 0.0319(7) 0.0505(9) 0.0038(7) 0.0000(7) 0.0021(6) S5 0.0674(11) 0.0372(8) 0.0308(8) -0.0062(6) 0.0064(8) 0.0003(7) O1 0.032(2) 0.0378(19) 0.024(2) -0.0002(15) 0.0018(18) -0.0024(17) O2 0.049(3) 0.130(4) 0.030(2) 0.008(2) -0.013(2) -0.039(3) O3 0.026(2) 0.0348(19) 0.037(2) 0.0076(15) -0.0016(17) -0.0011(15) O4 0.054(3) 0.055(2) 0.026(2) 0.0023(17) -0.008(2) -0.019(2) C1 0.030(3) 0.026(3) 0.058(4) -0.006(2) 0.011(3) 0.006(2) C2 0.028(3) 0.034(3) 0.037(4) -0.002(2) 0.007(3) 0.006(2) C3 0.041(3) 0.030(3) 0.038(4) -0.014(2) 0.003(3) -0.003(2) C4 0.023(3) 0.022(3) 0.033(3) 0.009(2) -0.001(2) -0.004(2) C5 0.027(3) 0.031(3) 0.027(3) -0.005(2) 0.005(3) 0.001(2) C6 0.036(3) 0.029(3) 0.029(3) -0.002(2) -0.002(3) -0.001(2) C7 0.043(4) 0.054(3) 0.033(3) -0.004(3) -0.001(3) -0.012(3) C8 0.034(4) 0.081(4) 0.030(4) -0.005(3) 0.001(3) -0.013(3) C9 0.067(5) 0.095(5) 0.042(4) 0.029(4) 0.002(4) -0.007(4) C10 0.077(5) 0.070(5) 0.047(4) -0.021(3) 0.021(4) -0.015(4) C11 0.030(3) 0.034(3) 0.029(3) 0.002(2) 0.003(3) 0.001(2) C12 0.027(3) 0.063(4) 0.043(4) 0.025(3) -0.004(3) -0.007(3) C13 0.033(3) 0.041(3) 0.029(3) 0.006(2) -0.003(3) -0.003(3) C14 0.047(4) 0.040(3) 0.050(4) 0.013(3) -0.010(3) -0.003(3) C15 0.063(5) 0.067(4) 0.057(5) 0.006(4) 0.032(4) 0.003(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 C1 1.646(5) . ? S2 C1 1.738(5) . ? S2 C2 1.742(5) . ? S3 C1 1.723(6) . ? S3 C3 1.747(5) . ? S4 C2 1.754(5) . ? S4 C4 1.839(5) . ? S5 C3 1.750(6) . ? S5 C5 1.827(5) . ? O1 C6 1.411(5) . ? O1 C8 1.420(6) . ? O2 C7 1.419(6) . ? O2 C8 1.419(6) . ? O3 C11 1.427(5) . ? O3 C13 1.429(6) . ? O4 C12 1.414(6) . ? O4 C13 1.427(6) . ? C2 C3 1.326(7) . ? C4 C6 1.532(6) . ? C4 C5 1.533(7) . ? C5 C11 1.538(7) . ? C6 C7 1.555(7) . ? C8 C9 1.513(8) . ? C8 C10 1.529(8) . ? C11 C12 1.526(7) . ? C13 C15 1.496(7) . ? C13 C14 1.525(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S2 C2 96.5(3) . . ? C1 S3 C3 96.8(3) . . ? C2 S4 C4 101.3(2) . . ? C3 S5 C5 94.3(2) . . ? C6 O1 C8 107.2(4) . . ? C7 O2 C8 108.7(4) . . ? C11 O3 C13 107.2(4) . . ? C12 O4 C13 106.0(4) . . ? S1 C1 S3 123.6(3) . . ? S1 C1 S2 123.2(3) . . ? S3 C1 S2 113.2(3) . . ? C3 C2 S2 116.9(4) . . ? C3 C2 S4 121.9(4) . . ? S2 C2 S4 121.3(3) . . ? C2 C3 S3 116.4(4) . . ? C2 C3 S5 121.9(4) . . ? S3 C3 S5 121.6(3) . . ? C6 C4 C5 109.9(4) . . ? C6 C4 S4 110.3(3) . . ? C5 C4 S4 115.8(3) . . ? C4 C5 C11 111.2(4) . . ? C4 C5 S5 113.9(3) . . ? C11 C5 S5 109.3(3) . . ? O1 C6 C4 109.8(4) . . ? O1 C6 C7 104.9(4) . . ? C4 C6 C7 114.5(4) . . ? O2 C7 C6 103.2(4) . . ? O2 C8 O1 104.3(4) . . ? O2 C8 C9 108.0(5) . . ? O1 C8 C9 108.9(5) . . ? O2 C8 C10 111.0(5) . . ? O1 C8 C10 110.0(5) . . ? C9 C8 C10 114.2(5) . . ? O3 C11 C12 103.8(4) . . ? O3 C11 C5 108.8(4) . . ? C12 C11 C5 115.2(4) . . ? O4 C12 C11 105.5(4) . . ? O4 C13 O3 103.8(4) . . ? O4 C13 C15 108.5(4) . . ? O3 C13 C15 109.5(5) . . ? O4 C13 C14 110.2(4) . . ? O3 C13 C14 110.5(4) . . ? C15 C13 C14 113.8(5) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.330 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.077