# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_exp_735 _audit_creation_date 2012-12-21 _audit_creation_method ; Olex2 1.2 (compiled Nov 5 2012 18:22:26, GUI svn.r4372) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H8 N2 O2 S2' _chemical_formula_sum 'C8 H8 N2 O2 S2' _chemical_formula_weight 228.28 _chemical_melting_point ? _chemical_oxdiff_formula C7H4O2N2S2 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 triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 10.3197(9) _cell_length_b 10.5653(9) _cell_length_c 10.8549(9) _cell_angle_alpha 117.738(9) _cell_angle_beta 104.820(7) _cell_angle_gamma 102.452(7) _cell_volume 931.99(14) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2115 _cell_measurement_temperature 180.00(10) _cell_measurement_theta_max 30.1558 _cell_measurement_theta_min 3.1579 _exptl_absorpt_coefficient_mu 0.543 _exptl_absorpt_correction_T_max 0.94700 _exptl_absorpt_correction_T_min 0.87800 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_unetI/netI 0.0956 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 5748 _diffrn_reflns_theta_full 26.02 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_min 3.16 _diffrn_ambient_temperature 180.00(10) _diffrn_detector_area_resol_mean 10.3914 _diffrn_measured_fraction_theta_full 0.9886 _diffrn_measured_fraction_theta_max 0.9836 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -10.00 79.00 1.0000 7.2200 omega____ theta____ kappa____ phi______ frames - 13.6605 57.0000 -150.0000 89 #__ type_ start__ end____ width___ exp.time_ 2 omega -85.00 12.00 1.0000 7.2200 omega____ theta____ kappa____ phi______ frames - -14.4417 -57.0000 -90.0000 97 #__ type_ start__ end____ width___ exp.time_ 3 omega -32.00 52.00 1.0000 7.2200 omega____ theta____ kappa____ phi______ frames - -14.4417 57.0000 60.0000 84 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0276601000 _diffrn_orient_matrix_UB_12 -0.0632681000 _diffrn_orient_matrix_UB_13 0.0062873000 _diffrn_orient_matrix_UB_21 0.0646333000 _diffrn_orient_matrix_UB_22 0.0321974000 _diffrn_orient_matrix_UB_23 0.0658097000 _diffrn_orient_matrix_UB_31 -0.0320205000 _diffrn_orient_matrix_UB_32 0.0418704000 _diffrn_orient_matrix_UB_33 0.0468505000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2505 _reflns_number_total 3640 _reflns_odcompleteness_completeness 98.86 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 27.42 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _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 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.379 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.088 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 263 _refine_ls_number_reflns 3640 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0506 _refine_ls_restrained_S_all 1.003 _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^)+(0.0231P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0941 _refine_ls_wR_factor_ref 0.1109 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: {H10A,H10B} of C10, {H3A,H3B} of C3, {H2A,H2B} of C2, {H11A,H11B} of C11 At 1.5 times of: {H8A,H8B,H8C} of C8, {H16A,H16B,H16C} of C16 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C10(H10A,H10B), C11(H11A,H11B) 2.b Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C16(H16A,H16B,H16C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _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 0.9019(3) 0.9492(3) 0.2771(4) 0.0177(7) Uani 1 1 d . . . C2 C 0.8176(4) 0.9157(3) 0.1236(4) 0.0225(7) Uani 1 1 d . . . H2A H 0.8139 1.0139 0.1368 0.027 Uiso 1 1 calc R . . H2B H 0.7164 0.8438 0.0847 0.027 Uiso 1 1 calc R . . C3 C 0.8757(4) 0.8453(3) 0.0025(4) 0.0231(7) Uani 1 1 d . . . H3A H 0.8429 0.8707 -0.0741 0.028 Uiso 1 1 calc R . . H3B H 0.9834 0.8930 0.0514 0.028 Uiso 1 1 calc R . . C4 C 0.8264(4) 0.6722(3) -0.0776(4) 0.0210(7) Uani 1 1 d . . . C5 C 0.8385(3) 0.6104(3) 0.0173(4) 0.0181(7) Uani 1 1 d . . . C6 C 0.8840(3) 0.6774(3) 0.1707(4) 0.0171(7) Uani 1 1 d . . . C7 C 0.8464(4) 0.4382(3) 0.1041(4) 0.0213(7) Uani 1 1 d . . . C8 C 0.9362(4) 0.3752(4) 0.3170(4) 0.0344(9) Uani 1 1 d . . . H8A H 1.0339 0.4461 0.3476 0.052 Uiso 1 1 calc R . . H8B H 0.9438 0.2982 0.3418 0.052 Uiso 1 1 calc R . . H8C H 0.8863 0.4345 0.3719 0.052 Uiso 1 1 calc R . . C9 C 0.5487(3) 0.5391(3) 0.2194(4) 0.0185(7) Uani 1 1 d . . . C10 C 0.5696(4) 0.5599(3) 0.3700(4) 0.0238(8) Uani 1 1 d . . . H10A H 0.5524 0.4575 0.3565 0.029 Uiso 1 1 calc R . . H10B H 0.4944 0.5940 0.4000 0.029 Uiso 1 1 calc R . . C11 C 0.7177(4) 0.6747(3) 0.5005(4) 0.0237(8) Uani 1 1 d . . . H11A H 0.7356 0.6471 0.5771 0.028 Uiso 1 1 calc R . . H11B H 0.7936 0.6651 0.4605 0.028 Uiso 1 1 calc R . . C12 C 0.7321(4) 0.8411(3) 0.5783(4) 0.0208(7) Uani 1 1 d . . . C13 C 0.6736(4) 0.8921(3) 0.4806(4) 0.0199(7) Uani 1 1 d . . . C14 C 0.6067(3) 0.8200(3) 0.3262(4) 0.0170(7) Uani 1 1 d . . . C15 C 0.6227(4) 1.0541(3) 0.3920(4) 0.0218(7) Uani 1 1 d . . . C16 C 0.4939(4) 1.1081(4) 0.1793(4) 0.0368(10) Uani 1 1 d . . . H16A H 0.5277 1.0310 0.1184 0.055 Uiso 1 1 calc R . . H16B H 0.4959 1.1823 0.1489 0.055 Uiso 1 1 calc R . . H16C H 0.3941 1.0555 0.1619 0.055 Uiso 1 1 calc R . . N1 N 0.9278(3) 0.8316(3) 0.2870(3) 0.0186(6) Uani 1 1 d . . . N2 N 0.8902(3) 0.5806(2) 0.2219(3) 0.0194(6) Uani 1 1 d . . . N3 N 0.5688(3) 0.6667(3) 0.2111(3) 0.0182(6) Uani 1 1 d . . . N4 N 0.5774(3) 0.9117(2) 0.2743(3) 0.0188(6) Uani 1 1 d . . . O1 O 0.9452(2) 1.0776(2) 0.3954(2) 0.0209(5) Uani 1 1 d . . . O2 O 0.7816(3) 0.5850(2) -0.2164(3) 0.0305(6) Uani 1 1 d . . . O3 O 0.5102(2) 0.4115(2) 0.1019(2) 0.0242(5) Uani 1 1 d . . . O4 O 0.7905(3) 0.9313(2) 0.7169(3) 0.0290(6) Uani 1 1 d . . . S1 S 0.79746(9) 0.41261(8) -0.07116(9) 0.0242(2) Uani 1 1 d . . . S2 S 0.83538(11) 0.27865(8) 0.11687(11) 0.0318(2) Uani 1 1 d . . . S3 S 0.69956(9) 1.08692(8) 0.56853(9) 0.0226(2) Uani 1 1 d . . . S4 S 0.61055(10) 1.20921(8) 0.37729(10) 0.0281(2) Uani 1 1 d . . . H1 H 0.961(3) 0.849(3) 0.370(4) 0.007(7) Uiso 1 1 d . . . H3 H 0.557(4) 0.653(3) 0.131(4) 0.013(8) 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 0.0181(19) 0.0201(15) 0.0144(17) 0.0100(14) 0.0076(16) 0.0041(13) C2 0.030(2) 0.0201(15) 0.0131(17) 0.0092(14) 0.0041(17) 0.0083(14) C3 0.022(2) 0.0307(16) 0.0135(17) 0.0150(15) 0.0028(16) 0.0042(14) C4 0.0158(19) 0.0316(16) 0.0134(17) 0.0118(15) 0.0048(16) 0.0083(14) C5 0.0154(19) 0.0212(15) 0.0133(17) 0.0074(14) 0.0051(16) 0.0055(13) C6 0.0146(19) 0.0179(14) 0.0126(17) 0.0056(13) 0.0047(15) 0.0037(12) C7 0.019(2) 0.0214(15) 0.0176(18) 0.0086(14) 0.0068(16) 0.0048(13) C8 0.044(3) 0.0300(17) 0.026(2) 0.0175(17) 0.009(2) 0.0125(17) C9 0.0160(19) 0.0207(15) 0.0142(17) 0.0082(14) 0.0033(16) 0.0065(13) C10 0.032(2) 0.0228(15) 0.0162(18) 0.0121(15) 0.0083(18) 0.0096(15) C11 0.030(2) 0.0271(16) 0.0168(18) 0.0149(15) 0.0073(18) 0.0123(15) C12 0.0158(19) 0.0313(16) 0.0107(17) 0.0107(15) 0.0045(16) 0.0047(14) C13 0.024(2) 0.0194(15) 0.0124(17) 0.0073(14) 0.0059(16) 0.0076(14) C14 0.0192(19) 0.0195(14) 0.0128(16) 0.0088(13) 0.0078(16) 0.0074(13) C15 0.027(2) 0.0202(15) 0.0211(19) 0.0116(15) 0.0144(18) 0.0087(14) C16 0.057(3) 0.0318(18) 0.020(2) 0.0145(17) 0.010(2) 0.0197(19) N1 0.0276(18) 0.0174(13) 0.0059(14) 0.0057(12) 0.0032(14) 0.0071(11) N2 0.0203(17) 0.0200(13) 0.0158(15) 0.0100(12) 0.0052(14) 0.0069(11) N3 0.0258(18) 0.0184(13) 0.0059(14) 0.0051(12) 0.0047(14) 0.0071(11) N4 0.0235(17) 0.0188(12) 0.0112(14) 0.0073(12) 0.0055(13) 0.0077(11) O1 0.0277(14) 0.0156(10) 0.0110(12) 0.0042(9) 0.0041(11) 0.0061(9) O2 0.0356(17) 0.0342(12) 0.0128(13) 0.0099(11) 0.0075(13) 0.0092(11) O3 0.0326(16) 0.0205(10) 0.0135(12) 0.0069(10) 0.0061(12) 0.0102(10) O4 0.0302(16) 0.0325(12) 0.0114(13) 0.0095(11) 0.0019(12) 0.0048(11) S1 0.0286(6) 0.0196(4) 0.0120(4) 0.0028(3) 0.0041(4) 0.0079(4) S2 0.0414(6) 0.0176(4) 0.0252(5) 0.0094(4) 0.0054(5) 0.0087(4) S3 0.0282(6) 0.0186(4) 0.0109(4) 0.0037(3) 0.0055(4) 0.0060(3) S4 0.0385(6) 0.0198(4) 0.0217(5) 0.0102(4) 0.0094(5) 0.0106(4) _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 C1 C2 1.495(4) . ? C1 N1 1.371(3) . ? C1 O1 1.230(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.525(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.501(4) . ? C4 C5 1.448(4) . ? C4 O2 1.225(4) . ? C5 C6 1.362(4) . ? C5 S1 1.735(3) . ? C6 N1 1.388(3) . ? C6 N2 1.379(3) . ? C7 N2 1.312(4) . ? C7 S1 1.708(3) . ? C7 S2 1.737(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C8 S2 1.779(4) . ? C9 C10 1.494(4) . ? C9 N3 1.368(3) . ? C9 O3 1.229(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C11 1.519(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.505(4) . ? C12 C13 1.457(4) . ? C12 O4 1.220(4) . ? C13 C14 1.363(4) . ? C13 S3 1.738(2) . ? C14 N3 1.389(3) . ? C14 N4 1.377(3) . ? C15 N4 1.310(4) . ? C15 S3 1.705(3) . ? C15 S4 1.746(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16 S4 1.787(4) . ? N1 H1 0.79(3) . ? N3 H3 0.78(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 N1 C1 C2 118.9(2) . . ? O1 C1 C2 122.2(2) . . ? O1 C1 N1 118.8(3) . . ? C1 C2 H2A 108.2 . . ? C1 C2 H2B 108.2 . . ? C1 C2 C3 116.2(3) . . ? H2A C2 H2B 107.4 . . ? C3 C2 H2A 108.2 . . ? C3 C2 H2B 108.2 . . ? C2 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C4 C3 C2 113.0(2) . . ? C4 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C5 C4 C3 117.0(3) . . ? O2 C4 C3 122.6(3) . . ? O2 C4 C5 120.3(3) . . ? C4 C5 S1 117.8(2) . . ? C6 C5 C4 133.1(3) . . ? C6 C5 S1 109.0(2) . . ? C5 C6 N1 129.8(3) . . ? C5 C6 N2 116.6(2) . . ? N2 C6 N1 113.5(3) . . ? N2 C7 S1 116.5(2) . . ? N2 C7 S2 124.2(2) . . ? S1 C7 S2 119.31(17) . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? S2 C8 H8A 109.5 . . ? S2 C8 H8B 109.5 . . ? S2 C8 H8C 109.5 . . ? N3 C9 C10 118.6(2) . . ? O3 C9 C10 122.7(2) . . ? O3 C9 N3 118.7(3) . . ? C9 C10 H10A 108.3 . . ? C9 C10 H10B 108.3 . . ? C9 C10 C11 116.1(2) . . ? H10A C10 H10B 107.4 . . ? C11 C10 H10A 108.3 . . ? C11 C10 H10B 108.3 . . ? C10 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C12 C11 C10 113.7(3) . . ? C12 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C13 C12 C11 117.1(3) . . ? O4 C12 C11 122.4(3) . . ? O4 C12 C13 120.5(3) . . ? C12 C13 S3 117.5(2) . . ? C14 C13 C12 133.3(2) . . ? C14 C13 S3 109.1(2) . . ? C13 C14 N3 129.2(3) . . ? C13 C14 N4 116.5(2) . . ? N4 C14 N3 114.2(3) . . ? N4 C15 S3 117.0(2) . . ? N4 C15 S4 123.9(3) . . ? S3 C15 S4 119.16(17) . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? S4 C16 H16A 109.5 . . ? S4 C16 H16B 109.5 . . ? S4 C16 H16C 109.5 . . ? C1 N1 C6 128.7(3) . . ? C1 N1 H1 116.4(18) . . ? C6 N1 H1 114.1(18) . . ? C7 N2 C6 108.9(3) . . ? C9 N3 C14 128.9(3) . . ? C9 N3 H3 116.9(19) . . ? C14 N3 H3 114.3(19) . . ? C15 N4 C14 108.8(3) . . ? C7 S1 C5 89.00(13) . . ? C7 S2 C8 99.90(15) . . ? C15 S3 C13 88.70(14) . . ? C15 S4 C16 100.74(15) . . ? _database_code_depnum_ccdc_archive 'CCDC 969335'