# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_rtfdd2 _audit_creation_date 2012-09-05 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.08.08 svn.r2439, GUI svn.r4300) ; _chemical_name_common 'oxobenzene bisdithiazolyl' _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H N2 O S4' _chemical_formula_sum 'C6 H N2 O S4' _chemical_formula_weight 245.33 _chemical_absolute_configuration ad _chemical_melting_point ? 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' _space_group_crystal_system orthorhombic _space_group_IT_number 43 _space_group_name_H-M_alt 'F d d 2' _space_group_name_Hall 'F 2 -2d' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z' 3 'x+1/4, -y+1/4, z+1/4' 4 '-x+1/4, y+1/4, z+1/4' 5 'x, y+1/2, z+1/2' 6 '-x, -y+1/2, z+1/2' 7 'x+1/4, -y+3/4, z+3/4' 8 '-x+1/4, y+3/4, z+3/4' 9 'x+1/2, y, z+1/2' 10 '-x+1/2, -y, z+1/2' 11 'x+3/4, -y+1/4, z+3/4' 12 '-x+3/4, y+1/4, z+3/4' 13 'x+1/2, y+1/2, z' 14 '-x+1/2, -y+1/2, z' 15 'x+3/4, -y+3/4, z+1/4' 16 '-x+3/4, y+3/4, z+1/4' _cell_length_a 27.876(3) _cell_length_b 31.252(4) _cell_length_c 4.0004(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3485.2(7) _cell_formula_units_Z 16 _cell_measurement_reflns_used 6808 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.89 _cell_measurement_theta_min 2.99 _exptl_absorpt_coefficient_mu 1.042 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_correction_T_min 0.6924 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details sadabs _exptl_crystal_colour black _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1968 _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.010 _exptl_crystal_size_min 0.002 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_unetI/netI 0.0274 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 14327 _diffrn_reflns_theta_full 26.93 _diffrn_reflns_theta_max 26.93 _diffrn_reflns_theta_min 1.96 _diffrn_ambient_temperature 296.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type Synchrotron _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator 'fine-focus mirrors' _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.6889 _diffrn_source synchrotron _diffrn_standards_number 0 _reflns_number_gt 1771 _reflns_number_total 1873 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Rigaku CrystalClear' _computing_data_collection 'Rigaku CrystalClear' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.227 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.044 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(8) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 122 _refine_ls_number_reflns 1873 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0256 _refine_ls_R_factor_gt 0.0235 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0274P)^2^+0.1323P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.0533 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C1 C 0.36277(8) 0.58561(6) 0.0273(6) 0.0301(5) Uani 1 1 d . . . C2 C 0.38117(7) 0.54100(6) 0.1232(6) 0.0280(4) Uani 1 1 d . . . C3 C 0.34999(7) 0.51071(6) 0.3071(5) 0.0287(5) Uani 1 1 d . . . C4 C 0.30280(7) 0.52163(6) 0.4160(6) 0.0296(4) Uani 1 1 d . . . C5 C 0.28504(7) 0.56411(6) 0.3462(5) 0.0273(4) Uani 1 1 d . . . C6 C 0.31325(7) 0.59640(6) 0.1662(5) 0.0271(4) Uani 1 1 d . . . N1 N 0.29427(6) 0.63650(5) 0.1175(5) 0.0360(4) Uani 1 1 d . . . N2 N 0.42624(6) 0.52893(6) 0.0322(5) 0.0393(5) Uani 1 1 d . . . O1 O 0.38648(6) 0.61060(5) -0.1582(5) 0.0466(4) Uani 1 1 d . . . S1 S 0.23902(2) 0.644890(16) 0.27687(16) 0.03775(15) Uani 1 1 d . . . S2 S 0.226415(19) 0.581719(17) 0.47338(15) 0.03392(14) Uani 1 1 d . . . S3 S 0.376853(19) 0.459296(16) 0.37644(16) 0.03613(14) Uani 1 1 d . . . S4 S 0.44209(2) 0.478976(18) 0.13848(17) 0.04133(16) Uani 1 1 d . . . H4 H 0.2818(8) 0.5009(7) 0.548(6) 0.033(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0263(11) 0.0266(11) 0.0373(11) 0.0011(9) 0.0010(9) -0.0042(8) C2 0.0215(11) 0.0288(10) 0.0338(10) -0.0016(9) -0.0005(9) -0.0009(8) C3 0.0261(11) 0.0253(9) 0.0348(12) -0.0001(8) -0.0047(9) -0.0001(8) C4 0.0269(11) 0.0272(9) 0.0348(11) 0.0048(9) 0.0028(10) -0.0041(8) C5 0.0221(10) 0.0307(10) 0.0291(10) -0.0013(9) 0.0009(9) -0.0010(8) C6 0.0230(11) 0.0259(9) 0.0325(11) -0.0012(9) -0.0007(9) -0.0008(8) N1 0.0311(10) 0.0283(8) 0.0484(11) 0.0019(8) 0.0040(9) -0.0001(7) N2 0.0279(10) 0.0333(10) 0.0567(13) 0.0009(9) 0.0025(10) 0.0011(8) O1 0.0368(9) 0.0358(8) 0.0672(12) 0.0130(8) 0.0174(9) -0.0012(7) S1 0.0326(3) 0.0311(3) 0.0496(3) 0.0021(2) 0.0059(3) 0.0058(2) S2 0.0261(3) 0.0346(3) 0.0410(3) 0.0013(2) 0.0069(2) 0.0007(2) S3 0.0288(3) 0.0284(3) 0.0511(3) 0.0057(2) -0.0021(3) 0.0015(2) S4 0.0271(3) 0.0361(3) 0.0608(4) 0.0031(3) 0.0030(3) 0.0053(2) _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 S3 S4 2.1427(8) . ? S3 C3 1.7944(19) . ? S4 N2 1.6774(19) . ? S1 S2 2.1539(8) . ? S1 N1 1.6872(19) . ? S2 C5 1.798(2) . ? C2 C1 1.534(3) . ? C2 N2 1.361(3) . ? C2 C3 1.481(3) . ? C1 O1 1.264(2) . ? C1 C6 1.526(3) . ? C4 C3 1.427(3) . ? C4 C5 1.444(3) . ? N1 C6 1.374(2) . ? C6 C5 1.468(3) . ? 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 S3 S4 91.63(7) . . ? N2 S4 S3 98.99(7) . . ? N1 S1 S2 98.30(6) . . ? C5 S2 S1 91.66(7) . . ? N2 C2 C1 119.56(18) . . ? N2 C2 C3 119.83(17) . . ? C3 C2 C1 120.59(17) . . ? O1 C1 C2 122.24(19) . . ? O1 C1 C6 123.40(17) . . ? C6 C1 C2 114.34(17) . . ? C3 C4 C5 118.48(18) . . ? C6 N1 S1 116.08(14) . . ? N1 C6 C1 119.89(17) . . ? N1 C6 C5 119.34(17) . . ? C5 C6 C1 120.76(17) . . ? C2 N2 S4 115.67(15) . . ? C2 C3 S3 113.85(15) . . ? C4 C3 S3 123.48(15) . . ? C4 C3 C2 122.67(17) . . ? C4 C5 S2 122.57(15) . . ? C4 C5 C6 122.88(18) . . ? C6 C5 S2 114.55(14) . . ? _database_code_depnum_ccdc_archive 'CCDC 957990'