# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Partha Basu' 'Eranda Perera' _publ_contact_author_name 'Partha Basu' _publ_contact_author_email BASU@DUQ.EDU _publ_section_title ; Synthesis, characterization and structure of a Low coordinate Desoxomolybdenum cluster stabilized by a Dithione Ligand ; # Attachment 'Dalton_cif_combined.cif' data_test_0m _database_code_depnum_ccdc_archive 'CCDC 722174' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C40H72Mo4N8S8C4H6N2B4F16 _chemical_formula_sum 'C44 H78 B4 F16 Mo4 N10 S8' _chemical_formula_weight 1734.64 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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' Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7098(10) _cell_length_b 12.6842(13) _cell_length_c 13.9239(14) _cell_angle_alpha 88.556(2) _cell_angle_beta 79.629(2) _cell_angle_gamma 83.0930(10) _cell_volume 1674.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8013 _cell_measurement_theta_min 4.39 _cell_measurement_theta_max 50.38 _exptl_crystal_description Plates _exptl_crystal_colour Bronze _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 1.066 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.664 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker smart Apex2' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15774 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.56 _reflns_number_total 6216 _reflns_number_gt 5582 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0667P)^2^+8.2823P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6216 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1397 _refine_ls_wR_factor_gt 0.1318 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 Mo1 Mo 0.44066(4) 0.18284(3) 0.08275(3) 0.02388(13) Uani 1 1 d . . . Mo2 Mo 0.42459(4) -0.04603(3) 0.14465(3) 0.02716(14) Uani 1 1 d . . . S1 S 0.53903(13) 0.23850(10) -0.08000(9) 0.0261(3) Uani 1 1 d . . . S2 S 0.21898(13) 0.08982(10) 0.15564(10) 0.0304(3) Uani 1 1 d . . . S3 S 0.48051(13) 0.18037(11) 0.25328(10) 0.0318(3) Uani 1 1 d . . . S4 S 0.68811(15) -0.06836(11) 0.12589(12) 0.0383(3) Uani 1 1 d . . . N2 N 0.0683(4) 0.1838(3) 0.3141(3) 0.0297(9) Uani 1 1 d . . . C4 C 0.0491(6) 0.2304(5) 0.4113(4) 0.0350(12) Uani 1 1 d . . . H4A H -0.0474 0.2285 0.4445 0.042 Uiso 1 1 calc R . . H4B H 0.0679 0.3040 0.4057 0.042 Uiso 1 1 calc R . . N1 N 0.2940(5) 0.1688(4) 0.4140(3) 0.0316(10) Uani 1 1 d . . . C10 C 0.1956(5) 0.1491(4) 0.2676(4) 0.0261(10) Uani 1 1 d . . . C3 C -0.1249(6) 0.0751(5) 0.3179(5) 0.0456(15) Uani 1 1 d . . . H3A H -0.0523 0.0159 0.3124 0.068 Uiso 1 1 calc R . . H3B H -0.1977 0.0594 0.2839 0.068 Uiso 1 1 calc R . . H3C H -0.1641 0.0878 0.3855 0.068 Uiso 1 1 calc R . . C5 C 0.1481(6) 0.1688(5) 0.4682(4) 0.0385(13) Uani 1 1 d . . . H5A H 0.1394 0.2007 0.5319 0.046 Uiso 1 1 calc R . . H5B H 0.1252 0.0964 0.4775 0.046 Uiso 1 1 calc R . . C9 C 0.3186(5) 0.1660(4) 0.3181(4) 0.0274(11) Uani 1 1 d . . . C6 C 0.4062(6) 0.1748(5) 0.4730(4) 0.0348(12) Uani 1 1 d . . . H6 H 0.4959 0.1453 0.4336 0.042 Uiso 1 1 calc R . . C2 C -0.0622(6) 0.1739(5) 0.2730(4) 0.0355(12) Uani 1 1 d . . . H2 H -0.0354 0.1638 0.2022 0.043 Uiso 1 1 calc R . . C7 C 0.4167(7) 0.2904(5) 0.4929(5) 0.0471(15) Uani 1 1 d . . . H7A H 0.4391 0.3273 0.4320 0.071 Uiso 1 1 calc R . . H7B H 0.4894 0.2946 0.5306 0.071 Uiso 1 1 calc R . . H7C H 0.3282 0.3224 0.5285 0.071 Uiso 1 1 calc R . . C8 C 0.3817(7) 0.1085(6) 0.5646(5) 0.0504(17) Uani 1 1 d . . . H8A H 0.3057 0.1438 0.6106 0.076 Uiso 1 1 calc R . . H8B H 0.4658 0.0990 0.5925 0.076 Uiso 1 1 calc R . . H8C H 0.3580 0.0404 0.5488 0.076 Uiso 1 1 calc R . . C1 C -0.1657(6) 0.2740(5) 0.2923(5) 0.0450(15) Uani 1 1 d . . . H1A H -0.2081 0.2769 0.3602 0.068 Uiso 1 1 calc R . . H1B H -0.2378 0.2733 0.2534 0.068 Uiso 1 1 calc R . . H1C H -0.1168 0.3352 0.2756 0.068 Uiso 1 1 calc R . . C11 C 0.3825(5) 0.2746(4) -0.1206(4) 0.0263(10) Uani 1 1 d . . . C12 C 0.7307(5) -0.2001(4) 0.1101(4) 0.0283(11) Uani 1 1 d . . . N5 N 0.3557(5) 0.3673(3) -0.1610(3) 0.0304(9) Uani 1 1 d . . . N4 N 0.8631(5) -0.2460(4) 0.0926(3) 0.0309(10) Uani 1 1 d . . . C13 C 0.2130(6) 0.3974(5) -0.1853(4) 0.0347(12) Uani 1 1 d . . . H24A H 0.2057 0.3637 -0.2456 0.042 Uiso 1 1 calc R . . H24B H 0.1964 0.4738 -0.1938 0.042 Uiso 1 1 calc R . . C14 C 0.8931(6) -0.3620(4) 0.1034(4) 0.0340(12) Uani 1 1 d . . . H19A H 0.9874 -0.3801 0.1174 0.041 Uiso 1 1 calc R . . H19B H 0.8873 -0.3971 0.0434 0.041 Uiso 1 1 calc R . . C15 C 0.4551(6) 0.4495(4) -0.1784(4) 0.0356(12) Uani 1 1 d . . . H22 H 0.5476 0.4171 -0.1669 0.043 Uiso 1 1 calc R . . C16 C 1.1012(7) -0.2374(6) -0.0067(5) 0.0495(16) Uani 1 1 d . . . H16A H 1.1502 -0.2988 0.0191 0.074 Uiso 1 1 calc R . . H16B H 1.1666 -0.1877 -0.0308 0.074 Uiso 1 1 calc R . . H16C H 1.0583 -0.2584 -0.0591 0.074 Uiso 1 1 calc R . . C20 C 0.4705(7) 0.4868(5) -0.2844(5) 0.0487(16) Uani 1 1 d . . . H23A H 0.5065 0.4276 -0.3269 0.073 Uiso 1 1 calc R . . H23B H 0.5344 0.5398 -0.2955 0.073 Uiso 1 1 calc R . . H23C H 0.3801 0.5166 -0.2976 0.073 Uiso 1 1 calc R . . C18 C 0.9855(6) -0.1845(5) 0.0749(5) 0.0393(13) Uani 1 1 d . . . H18 H 0.9541 -0.1130 0.0531 0.047 Uiso 1 1 calc R . . C19 C 0.4036(7) 0.5396(5) -0.1064(5) 0.0439(14) Uani 1 1 d . . . H21A H 0.3183 0.5774 -0.1214 0.066 Uiso 1 1 calc R . . H21B H 0.4743 0.5871 -0.1108 0.066 Uiso 1 1 calc R . . H21C H 0.3856 0.5111 -0.0414 0.066 Uiso 1 1 calc R . . C17 C 1.0393(7) -0.1751(6) 0.1703(6) 0.0540(18) Uani 1 1 d . . . H17A H 0.9641 -0.1432 0.2190 0.081 Uiso 1 1 calc R . . H17B H 1.1151 -0.1316 0.1601 0.081 Uiso 1 1 calc R . . H17C H 1.0726 -0.2444 0.1918 0.081 Uiso 1 1 calc R . . F1 F 0.0401(4) 0.4215(3) 0.1427(3) 0.0482(9) Uani 1 1 d . . . F4 F 0.2035(4) 0.5325(3) 0.1524(3) 0.0450(8) Uani 1 1 d . . . F2 F 0.1971(5) 0.3835(3) 0.2461(3) 0.0525(10) Uani 1 1 d . . . F3 F 0.2697(4) 0.3707(3) 0.0820(3) 0.0478(9) Uani 1 1 d . . . B1 B 0.1784(7) 0.4276(5) 0.1565(5) 0.0322(13) Uani 1 1 d . . . F5 F 0.7229(5) 0.1867(5) 0.5301(3) 0.0798(16) Uani 1 1 d . . . F6 F 0.8858(5) 0.1616(5) 0.6235(4) 0.0844(16) Uani 1 1 d . . . F7 F 0.6595(7) 0.2154(6) 0.6873(4) 0.115(2) Uani 1 1 d . . . F8 F 0.7169(8) 0.0541(4) 0.6364(7) 0.137(3) Uani 1 1 d . . . B2 B 0.7480(7) 0.1536(6) 0.6190(5) 0.0374(14) Uani 1 1 d . . . C21 C 0.8223(9) 0.4320(7) 0.6046(7) 0.068(2) Uani 1 1 d . . . H26A H 0.7817 0.5048 0.6038 0.102 Uiso 1 1 calc R . . H26B H 0.7772 0.3973 0.6618 0.102 Uiso 1 1 calc R . . H26C H 0.8089 0.3968 0.5473 0.102 Uiso 1 1 calc R . . C22 C 0.9721(9) 0.4276(7) 0.6060(6) 0.064(2) Uani 1 1 d . . . N7 N 1.0882(9) 0.4254(9) 0.6072(6) 0.101(3) 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 Mo1 0.0217(2) 0.0261(2) 0.0223(2) 0.00347(16) -0.00193(16) -0.00059(16) Mo2 0.0202(2) 0.0208(2) 0.0375(3) -0.00520(17) -0.00220(18) 0.00589(16) S1 0.0213(6) 0.0272(6) 0.0294(6) -0.0009(5) -0.0049(5) -0.0008(5) S2 0.0223(6) 0.0307(6) 0.0379(7) -0.0068(5) -0.0056(5) -0.0002(5) S3 0.0216(6) 0.0409(7) 0.0330(7) 0.0002(6) -0.0044(5) -0.0052(5) S4 0.0295(7) 0.0242(6) 0.0626(10) -0.0082(6) -0.0125(6) -0.0010(5) N2 0.023(2) 0.031(2) 0.033(2) 0.0031(18) -0.0023(18) -0.0007(17) C4 0.028(3) 0.042(3) 0.031(3) -0.003(2) 0.003(2) -0.002(2) N1 0.027(2) 0.035(2) 0.033(2) 0.0035(19) -0.0061(19) -0.0046(18) C10 0.022(2) 0.021(2) 0.033(3) 0.0037(19) -0.002(2) -0.0013(18) C3 0.030(3) 0.043(3) 0.065(4) -0.013(3) -0.007(3) -0.006(3) C5 0.028(3) 0.052(4) 0.033(3) 0.003(3) -0.001(2) -0.006(2) C9 0.026(3) 0.021(2) 0.035(3) 0.001(2) -0.006(2) 0.0005(19) C6 0.029(3) 0.042(3) 0.035(3) 0.004(2) -0.010(2) -0.004(2) C2 0.022(3) 0.052(3) 0.032(3) -0.002(2) -0.006(2) 0.000(2) C7 0.043(4) 0.048(4) 0.054(4) -0.006(3) -0.019(3) -0.004(3) C8 0.038(3) 0.075(5) 0.041(3) 0.015(3) -0.014(3) -0.010(3) C1 0.025(3) 0.050(4) 0.058(4) 0.016(3) -0.006(3) 0.002(3) C11 0.026(3) 0.024(2) 0.027(3) -0.0035(19) -0.002(2) 0.0010(19) C12 0.026(3) 0.030(3) 0.030(3) -0.002(2) -0.008(2) -0.001(2) N5 0.026(2) 0.030(2) 0.036(2) 0.0008(18) -0.0093(19) -0.0002(18) N4 0.024(2) 0.029(2) 0.040(3) -0.0029(19) -0.0074(19) 0.0013(17) C13 0.032(3) 0.035(3) 0.040(3) 0.003(2) -0.014(2) -0.001(2) C14 0.026(3) 0.030(3) 0.047(3) -0.004(2) -0.010(2) 0.003(2) C15 0.030(3) 0.030(3) 0.046(3) 0.006(2) -0.006(2) -0.003(2) C16 0.031(3) 0.065(4) 0.051(4) 0.003(3) -0.004(3) -0.006(3) C20 0.047(4) 0.049(4) 0.045(4) 0.010(3) 0.004(3) -0.005(3) C18 0.025(3) 0.033(3) 0.060(4) 0.001(3) -0.009(3) -0.003(2) C19 0.049(4) 0.035(3) 0.049(4) 0.000(3) -0.011(3) -0.012(3) C17 0.037(3) 0.059(4) 0.070(5) -0.028(4) -0.013(3) -0.008(3) F1 0.0318(18) 0.0418(19) 0.071(3) -0.0048(17) -0.0068(17) -0.0047(15) F4 0.043(2) 0.0298(17) 0.064(2) 0.0052(16) -0.0133(17) -0.0069(14) F2 0.073(3) 0.042(2) 0.040(2) 0.0046(16) -0.0105(18) 0.0015(18) F3 0.043(2) 0.047(2) 0.046(2) -0.0037(16) 0.0018(16) 0.0115(16) B1 0.029(3) 0.029(3) 0.035(3) 0.001(2) -0.001(2) 0.000(2) F5 0.048(2) 0.145(5) 0.041(2) 0.025(3) -0.0061(19) 0.001(3) F6 0.045(3) 0.148(5) 0.062(3) 0.018(3) -0.012(2) -0.021(3) F7 0.092(4) 0.169(7) 0.073(4) -0.060(4) 0.024(3) -0.014(4) F8 0.134(6) 0.051(3) 0.245(9) 0.056(4) -0.082(6) -0.030(3) B2 0.040(4) 0.044(4) 0.030(3) 0.004(3) -0.009(3) -0.009(3) C21 0.062(5) 0.059(5) 0.081(6) -0.021(4) -0.007(4) -0.005(4) C22 0.058(5) 0.080(6) 0.048(4) -0.011(4) -0.010(4) 0.020(4) N7 0.056(5) 0.181(10) 0.056(4) -0.013(5) -0.011(4) 0.032(5) _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 Mo1 S1 2.4183(13) . ? Mo1 S3 2.4724(14) . ? Mo1 S2 2.6114(14) . ? Mo1 Mo2 3.0214(7) . ? Mo2 S2 2.4605(13) . ? Mo2 S4 2.5068(15) . ? Mo2 S1 2.5854(13) 2_655 ? S1 C11 1.723(5) . ? S1 Mo2 2.5854(13) 2_655 ? S2 C10 1.714(5) . ? S3 C9 1.694(5) . ? S4 C12 1.683(5) . ? N2 C10 1.317(7) . ? N2 C4 1.463(7) . ? N2 C2 1.501(7) . ? C4 C5 1.492(8) . ? N1 C9 1.314(7) . ? N1 C5 1.480(7) . ? N1 C6 1.487(7) . ? C10 C9 1.529(7) . ? C3 C2 1.529(9) . ? C6 C8 1.508(8) . ? C6 C7 1.518(9) . ? C2 C1 1.520(8) . ? C11 N5 1.308(7) . ? C11 C12 1.519(7) 2_655 ? C12 N4 1.328(7) . ? C12 C11 1.519(7) 2_655 ? N5 C13 1.488(7) . ? N5 C15 1.491(7) . ? N4 C14 1.475(7) . ? N4 C18 1.480(7) . ? C13 C14 1.492(8) 2_655 ? C14 C13 1.492(8) 2_655 ? C15 C19 1.517(8) . ? C15 C20 1.526(9) . ? C16 C18 1.549(9) . ? C18 C17 1.525(9) . ? F1 B1 1.401(7) . ? F4 B1 1.379(7) . ? F2 B1 1.387(7) . ? F3 B1 1.391(7) . ? F5 B2 1.351(8) . ? F6 B2 1.368(8) . ? F7 B2 1.356(9) . ? F8 B2 1.338(9) . ? C21 C22 1.453(12) . ? C22 N7 1.127(11) . ? 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 S1 Mo1 S3 141.97(5) . . ? S1 Mo1 S2 133.77(5) . . ? S3 Mo1 S2 84.26(4) . . ? S1 Mo1 Mo2 124.18(3) . . ? S3 Mo1 Mo2 76.36(4) . . ? S2 Mo1 Mo2 51.17(3) . . ? S2 Mo2 S4 142.39(5) . . ? S2 Mo2 S1 130.19(4) . 2_655 ? S4 Mo2 S1 84.17(4) . 2_655 ? S2 Mo2 Mo1 55.77(3) . . ? S4 Mo2 Mo1 87.94(4) . . ? S1 Mo2 Mo1 143.40(3) 2_655 . ? C11 S1 Mo1 97.78(18) . . ? C11 S1 Mo2 95.75(17) . 2_655 ? Mo1 S1 Mo2 92.09(4) . 2_655 ? C10 S2 Mo2 107.43(17) . . ? C10 S2 Mo1 94.47(17) . . ? Mo2 S2 Mo1 73.06(4) . . ? C9 S3 Mo1 102.66(19) . . ? C12 S4 Mo2 103.05(18) . . ? C10 N2 C4 120.2(5) . . ? C10 N2 C2 122.6(5) . . ? C4 N2 C2 117.2(4) . . ? N2 C4 C5 109.0(5) . . ? C9 N1 C5 119.8(5) . . ? C9 N1 C6 123.2(5) . . ? C5 N1 C6 117.0(4) . . ? N2 C10 C9 116.6(5) . . ? N2 C10 S2 120.7(4) . . ? C9 C10 S2 122.7(4) . . ? N1 C5 C4 109.0(5) . . ? N1 C9 C10 117.4(5) . . ? N1 C9 S3 121.1(4) . . ? C10 C9 S3 121.4(4) . . ? N1 C6 C8 111.2(5) . . ? N1 C6 C7 109.2(5) . . ? C8 C6 C7 113.3(6) . . ? N2 C2 C1 110.6(5) . . ? N2 C2 C3 108.0(5) . . ? C1 C2 C3 112.4(5) . . ? N5 C11 C12 117.3(4) . 2_655 ? N5 C11 S1 121.6(4) . . ? C12 C11 S1 121.1(4) 2_655 . ? N4 C12 C11 115.9(4) . 2_655 ? N4 C12 S4 122.9(4) . . ? C11 C12 S4 121.1(4) 2_655 . ? C11 N5 C13 118.6(4) . . ? C11 N5 C15 124.6(4) . . ? C13 N5 C15 116.7(4) . . ? C12 N4 C14 119.8(4) . . ? C12 N4 C18 122.7(4) . . ? C14 N4 C18 116.9(4) . . ? N5 C13 C14 108.2(4) . 2_655 ? N4 C14 C13 108.2(4) . 2_655 ? N5 C15 C19 109.4(5) . . ? N5 C15 C20 109.6(5) . . ? C19 C15 C20 112.7(5) . . ? N4 C18 C17 109.1(5) . . ? N4 C18 C16 110.2(5) . . ? C17 C18 C16 112.2(5) . . ? F4 B1 F2 110.3(5) . . ? F4 B1 F3 109.9(5) . . ? F2 B1 F3 109.6(5) . . ? F4 B1 F1 109.2(5) . . ? F2 B1 F1 109.8(5) . . ? F3 B1 F1 108.0(5) . . ? F8 B2 F5 110.7(7) . . ? F8 B2 F7 106.4(7) . . ? F5 B2 F7 108.1(6) . . ? F8 B2 F6 111.5(6) . . ? F5 B2 F6 109.0(5) . . ? F7 B2 F6 111.2(6) . . ? N7 C22 C21 179.2(11) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.56 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.214 _refine_diff_density_min -1.004 _refine_diff_density_rms 0.170 data_c2cfinal _database_code_depnum_ccdc_archive 'CCDC 722175' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Piperazenedithione _chemical_melting_point 164-166 _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 N2 S2' _chemical_formula_weight 230.38 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 C2/c loop_ _symmetry_equiv_pos_as_xyz '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, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.5301(7) _cell_length_b 7.0919(3) _cell_length_c 9.7843(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.344(3) _cell_angle_gamma 90.00 _cell_volume 1275.24(9) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2224 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.2 _exptl_crystal_description Needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.386 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.861431 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker smart Apex2' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16707 _diffrn_reflns_av_R_equivalents 0.0945 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.20 _reflns_number_total 1420 _reflns_number_gt 607 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker sAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1414P)^2^+4.5477P] 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 1420 _refine_ls_number_parameters 66 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2021 _refine_ls_R_factor_gt 0.0876 _refine_ls_wR_factor_ref 0.3081 _refine_ls_wR_factor_gt 0.2133 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 0.06644(11) 1.1908(3) 0.65287(19) 0.0787(8) Uani 1 1 d . . . N1 N 0.0741(3) 0.8373(6) 0.7423(5) 0.0546(13) Uani 1 1 d . . . C1 C 0.0386(3) 0.6671(7) 0.7824(6) 0.0577(15) Uani 1 1 d . . . H1A H 0.0407 0.6623 0.8819 0.069 Uiso 1 1 calc R . . H1B H 0.0635 0.5570 0.7527 0.069 Uiso 1 1 calc R . . C2 C 0.0369(3) 0.9963(7) 0.7251(5) 0.0530(14) Uani 1 1 d . . . C3 C 0.1492(4) 0.8176(11) 0.7074(8) 0.079(2) Uani 1 1 d . . . H3 H 0.1683 0.9449 0.6969 0.095 Uiso 1 1 calc R . . C4 C 0.1477(5) 0.7192(13) 0.5707(9) 0.108(3) Uani 1 1 d . . . H4A H 0.1302 0.5926 0.5781 0.162 Uiso 1 1 calc R . . H4B H 0.1960 0.7160 0.5448 0.162 Uiso 1 1 calc R . . H4C H 0.1161 0.7861 0.5019 0.162 Uiso 1 1 calc R . . C5 C 0.1969(5) 0.7244(16) 0.8234(10) 0.120(3) Uani 1 1 d . . . H5A H 0.1917 0.7880 0.9082 0.179 Uiso 1 1 calc R . . H5B H 0.2467 0.7309 0.8063 0.179 Uiso 1 1 calc R . . H5C H 0.1828 0.5948 0.8300 0.179 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 0.1015(16) 0.0580(11) 0.0792(12) 0.0097(8) 0.0221(10) -0.0163(9) N1 0.059(3) 0.045(3) 0.060(3) 0.000(2) 0.009(2) 0.002(2) C1 0.077(4) 0.038(3) 0.058(3) 0.005(2) 0.012(3) 0.004(3) C2 0.070(4) 0.045(3) 0.043(3) -0.001(2) 0.005(2) -0.007(3) C3 0.054(4) 0.086(5) 0.099(5) -0.006(4) 0.016(4) -0.001(4) C4 0.100(6) 0.136(8) 0.099(6) -0.006(5) 0.051(5) 0.006(5) C5 0.069(5) 0.158(9) 0.126(7) -0.003(7) -0.009(5) 0.024(5) _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 1.674(5) . ? N1 C2 1.321(7) . ? N1 C1 1.452(7) . ? N1 C3 1.482(8) . ? C1 C1 1.491(12) 2_556 ? C2 C2 1.509(11) 2_556 ? C3 C5 1.500(11) . ? C3 C4 1.506(10) . ? 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 N1 C1 119.9(5) . . ? C2 N1 C3 122.8(5) . . ? C1 N1 C3 117.0(5) . . ? N1 C1 C1 109.1(4) . 2_556 ? N1 C2 C2 116.0(3) . 2_556 ? N1 C2 S1 124.3(4) . . ? C2 C2 S1 119.7(3) 2_556 . ? N1 C3 C5 110.3(6) . . ? N1 C3 C4 109.7(6) . . ? C5 C3 C4 114.2(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.20 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.2 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.083