Electronic Supplementary MAterial for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Edward R. T. Tiekink' 'Ryan Phillip Anthony Bettens' 'Grant A. Broker' _publ_contact_author_name 'Edward R. T. Tiekink' _publ_contact_author_address ; Department of Chemistry The University of Texas at San Antonio One UTSA Circle San Antonio Texas 78249-0698 UNITED STATES OF AMERICA ; _publ_contact_author_email EDWARD.TIEKINK@UTSA.EDU _publ_requested_journal CrystEngComm _publ_section_title ; Co-crystallisation of 2,2'-dithiodibenzoic acid with the isomeric n-pyridinealdazines, n = 2, 3 and 4: supramolecular polymers and the influence of steric factors upon aggregation patterns ; data_shelxl _database_code_depnum_ccdc_archive 'CCDC 675039' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 O4 S2, 1.5(C12 H10 N4)' _chemical_formula_sum 'C32 H25 N6 O4 S2' _chemical_formula_weight 621.70 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7631(16) _cell_length_b 12.907(3) _cell_length_c 15.690(3) _cell_angle_alpha 100.40(3) _cell_angle_beta 103.54(3) _cell_angle_gamma 98.97(3) _cell_volume 1470.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5250 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 30.4 _exptl_crystal_description fragment _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 646 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.888 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 29076 _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_av_sigmaI/netI 0.024 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.3 _diffrn_reflns_theta_max 26.5 _reflns_number_total 6074 _reflns_number_gt 5945 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0361P)^2^+0.5114P] 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 6074 _refine_ls_number_parameters 403 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.037 _refine_ls_R_factor_gt 0.036 _refine_ls_wR_factor_ref 0.088 _refine_ls_wR_factor_gt 0.088 _refine_ls_goodness_of_fit_ref 1.10 _refine_ls_restrained_S_all 1.10 _refine_ls_shift/su_max 0.001 _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 0.21940(5) 0.90749(3) 0.29474(2) 0.02929(9) Uani 1 1 d . . . S2 S 0.14748(4) 0.74491(3) 0.24097(2) 0.02961(9) Uani 1 1 d . . . O1 O 0.35214(18) 1.21262(9) 0.49500(8) 0.0467(3) Uani 1 1 d D . . H1O H 0.3743 1.2630 0.4694 0.070 Uiso 1 1 d D . . O2 O 0.34415(16) 1.11693(8) 0.36017(7) 0.0393(3) Uani 1 1 d . . . O3 O -0.19068(14) 0.44241(8) 0.06630(8) 0.0396(3) Uani 1 1 d D . . H3O H -0.1250 0.3989 0.0544 0.059 Uiso 1 1 d D . . O4 O 0.07331(14) 0.54288(9) 0.15230(9) 0.0481(3) Uani 1 1 d . . . N1 N 0.39403(17) 1.37743(10) 0.41469(9) 0.0347(3) Uani 1 1 d . . . N2 N 0.05566(19) 1.51019(11) 0.47172(9) 0.0402(3) Uani 1 1 d . . . N3 N 0.02590(16) 0.30536(9) 0.03071(8) 0.0299(3) Uani 1 1 d . . . N4 N -0.26871(16) 0.05679(10) -0.09071(8) 0.0325(3) Uani 1 1 d . . . N5 N -0.45768(16) 0.02024(9) -0.11374(8) 0.0315(3) Uani 1 1 d . . . N6 N -0.72330(18) -0.23963(10) -0.21786(10) 0.0402(3) Uani 1 1 d . . . C1 C 0.21633(18) 0.92127(11) 0.41014(9) 0.0281(3) Uani 1 1 d . . . C2 C 0.26910(19) 1.02429(11) 0.46811(9) 0.0301(3) Uani 1 1 d . . . C3 C 0.2653(2) 1.03522(13) 0.55776(10) 0.0410(4) Uani 1 1 d . . . H3 H 0.3005 1.1047 0.5970 0.049 Uiso 1 1 calc R . . C4 C 0.2115(3) 0.94697(15) 0.59018(11) 0.0499(4) Uani 1 1 d . . . H4 H 0.2105 0.9554 0.6515 0.060 Uiso 1 1 calc R . . C5 C 0.1592(3) 0.84627(14) 0.53325(12) 0.0457(4) Uani 1 1 d . . . H5 H 0.1220 0.7853 0.5556 0.055 Uiso 1 1 calc R . . C6 C 0.1602(2) 0.83311(12) 0.44407(11) 0.0364(3) Uani 1 1 d . . . H6 H 0.1223 0.7633 0.4055 0.044 Uiso 1 1 calc R . . C7 C 0.32540(19) 1.12115(11) 0.43518(10) 0.0313(3) Uani 1 1 d . . . C8 C -0.09513(18) 0.71456(10) 0.20689(9) 0.0255(3) Uani 1 1 d . . . C9 C -0.18970(18) 0.61371(10) 0.15168(9) 0.0266(3) Uani 1 1 d . . . C10 C -0.37849(19) 0.59247(11) 0.12308(9) 0.0295(3) Uani 1 1 d . . . H10 H -0.4418 0.5246 0.0853 0.035 Uiso 1 1 calc R . . C11 C -0.47528(19) 0.66824(12) 0.14864(10) 0.0316(3) Uani 1 1 d . . . H11 H -0.6038 0.6530 0.1283 0.038 Uiso 1 1 calc R . . C12 C -0.3821(2) 0.76676(12) 0.20437(10) 0.0316(3) Uani 1 1 d . . . H12 H -0.4474 0.8191 0.2229 0.038 Uiso 1 1 calc R . . C13 C -0.19453(19) 0.78986(11) 0.23339(9) 0.0293(3) Uani 1 1 d . . . H13 H -0.1329 0.8577 0.2718 0.035 Uiso 1 1 calc R . . C14 C -0.08919(19) 0.53051(11) 0.12367(9) 0.0296(3) Uani 1 1 d . . . C15 C 0.2948(2) 1.45409(11) 0.41611(10) 0.0330(3) Uani 1 1 d . . . C16 C 0.3108(2) 1.53253(14) 0.36766(12) 0.0450(4) Uani 1 1 d . . . H16 H 0.2401 1.5863 0.3700 0.054 Uiso 1 1 calc R . . C17 C 0.4313(3) 1.53129(16) 0.31588(13) 0.0538(5) Uani 1 1 d . . . H17 H 0.4453 1.5848 0.2822 0.065 Uiso 1 1 calc R . . C18 C 0.5315(2) 1.45240(16) 0.31302(12) 0.0482(4) Uani 1 1 d . . . H18 H 0.6147 1.4502 0.2773 0.058 Uiso 1 1 calc R . . C19 C 0.5086(2) 1.37674(13) 0.36301(11) 0.0410(4) Uani 1 1 d . . . H19 H 0.5769 1.3218 0.3607 0.049 Uiso 1 1 calc R . . C20 C 0.1666(2) 1.44698(12) 0.47102(10) 0.0349(3) Uani 1 1 d . . . H20 H 0.1660 1.3947 0.5066 0.042 Uiso 1 1 calc R . . C21 C -0.02243(18) 0.20091(11) -0.01245(9) 0.0269(3) Uani 1 1 d . . . C22 C 0.1046(2) 0.13895(11) -0.02481(10) 0.0319(3) Uani 1 1 d . . . H22 H 0.0663 0.0651 -0.0549 0.038 Uiso 1 1 calc R . . C23 C 0.2864(2) 0.18533(12) 0.00684(10) 0.0331(3) Uani 1 1 d . . . H23 H 0.3750 0.1446 -0.0024 0.040 Uiso 1 1 calc R . . C24 C 0.3376(2) 0.29206(12) 0.05231(10) 0.0340(3) Uani 1 1 d . . . H24 H 0.4619 0.3259 0.0760 0.041 Uiso 1 1 calc R . . C25 C 0.2035(2) 0.34868(12) 0.06253(10) 0.0341(3) Uani 1 1 d . . . H25 H 0.2392 0.4221 0.0938 0.041 Uiso 1 1 calc R . . C26 C -0.21671(19) 0.15353(11) -0.04477(9) 0.0293(3) Uani 1 1 d . . . H26 H -0.3028 0.1944 -0.0316 0.035 Uiso 1 1 calc R . . C27 C -0.50519(19) -0.07557(11) -0.16200(10) 0.0314(3) Uani 1 1 d . . . H27 H -0.4168 -0.1104 -0.1808 0.038 Uiso 1 1 calc R . . C28 C -0.69521(19) -0.13244(11) -0.18874(9) 0.0293(3) Uani 1 1 d . . . C29 C -0.8948(2) -0.29398(14) -0.23826(12) 0.0456(4) Uani 1 1 d . . . H29 H -0.9182 -0.3701 -0.2582 0.055 Uiso 1 1 calc R . . C30 C -1.0397(2) -0.24589(15) -0.23201(11) 0.0442(4) Uani 1 1 d . . . H30 H -1.1586 -0.2883 -0.2466 0.053 Uiso 1 1 calc R . . C31 C -1.0092(2) -0.13587(14) -0.20445(10) 0.0406(4) Uani 1 1 d . . . H31 H -1.1067 -0.1006 -0.2008 0.049 Uiso 1 1 calc R . . C32 C -0.8337(2) -0.07777(12) -0.18211(10) 0.0333(3) Uani 1 1 d . . . H32 H -0.8081 -0.0016 -0.1625 0.040 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 0.03276(18) 0.02308(17) 0.02966(18) 0.00060(13) 0.01020(14) 0.00234(13) S2 0.02504(17) 0.02346(17) 0.03651(19) -0.00203(13) 0.00752(14) 0.00526(13) O1 0.0684(8) 0.0251(5) 0.0431(6) -0.0018(5) 0.0179(6) 0.0064(5) O2 0.0511(7) 0.0263(5) 0.0376(6) 0.0026(4) 0.0137(5) 0.0026(5) O3 0.0298(5) 0.0267(5) 0.0515(7) -0.0104(5) 0.0052(5) 0.0057(4) O4 0.0292(6) 0.0321(6) 0.0677(8) -0.0147(5) 0.0012(5) 0.0098(4) N1 0.0336(6) 0.0260(6) 0.0379(7) -0.0019(5) 0.0053(5) 0.0039(5) N2 0.0439(7) 0.0411(7) 0.0395(7) 0.0088(6) 0.0155(6) 0.0139(6) N3 0.0304(6) 0.0255(6) 0.0327(6) 0.0019(5) 0.0098(5) 0.0065(5) N4 0.0275(6) 0.0288(6) 0.0396(7) 0.0038(5) 0.0104(5) 0.0044(5) N5 0.0262(6) 0.0293(6) 0.0382(7) 0.0056(5) 0.0093(5) 0.0052(5) N6 0.0339(7) 0.0303(6) 0.0500(8) 0.0016(6) 0.0062(6) 0.0040(5) C1 0.0260(6) 0.0275(7) 0.0306(7) 0.0047(5) 0.0068(5) 0.0087(5) C2 0.0291(7) 0.0288(7) 0.0307(7) 0.0028(6) 0.0054(5) 0.0095(5) C3 0.0514(10) 0.0393(8) 0.0298(7) 0.0021(6) 0.0074(7) 0.0141(7) C4 0.0701(12) 0.0548(11) 0.0300(8) 0.0138(7) 0.0158(8) 0.0195(9) C5 0.0578(11) 0.0433(9) 0.0440(9) 0.0208(8) 0.0178(8) 0.0149(8) C6 0.0414(8) 0.0296(7) 0.0394(8) 0.0082(6) 0.0118(7) 0.0089(6) C7 0.0302(7) 0.0258(7) 0.0336(7) 0.0002(6) 0.0047(6) 0.0067(5) C8 0.0260(6) 0.0248(6) 0.0267(6) 0.0055(5) 0.0087(5) 0.0062(5) C9 0.0289(7) 0.0241(6) 0.0272(6) 0.0044(5) 0.0090(5) 0.0067(5) C10 0.0287(7) 0.0277(7) 0.0297(7) 0.0036(5) 0.0081(5) 0.0020(5) C11 0.0259(7) 0.0374(8) 0.0346(7) 0.0102(6) 0.0114(6) 0.0084(6) C12 0.0331(7) 0.0329(7) 0.0345(7) 0.0079(6) 0.0151(6) 0.0138(6) C13 0.0321(7) 0.0247(6) 0.0321(7) 0.0030(5) 0.0115(6) 0.0085(5) C14 0.0297(7) 0.0234(6) 0.0332(7) 0.0012(5) 0.0077(6) 0.0056(5) C15 0.0346(7) 0.0278(7) 0.0307(7) -0.0007(6) 0.0038(6) 0.0054(6) C16 0.0531(10) 0.0435(9) 0.0456(9) 0.0155(7) 0.0169(8) 0.0195(8) C17 0.0616(12) 0.0577(11) 0.0527(11) 0.0248(9) 0.0239(9) 0.0166(9) C18 0.0414(9) 0.0605(11) 0.0437(9) 0.0084(8) 0.0166(7) 0.0097(8) C19 0.0337(8) 0.0407(9) 0.0429(9) -0.0015(7) 0.0076(7) 0.0079(7) C20 0.0392(8) 0.0290(7) 0.0325(7) 0.0014(6) 0.0073(6) 0.0055(6) C21 0.0305(7) 0.0262(6) 0.0265(6) 0.0060(5) 0.0115(5) 0.0071(5) C22 0.0343(7) 0.0261(7) 0.0363(7) 0.0024(6) 0.0137(6) 0.0081(6) C23 0.0317(7) 0.0336(7) 0.0393(8) 0.0092(6) 0.0149(6) 0.0128(6) C24 0.0276(7) 0.0341(8) 0.0392(8) 0.0066(6) 0.0087(6) 0.0056(6) C25 0.0316(7) 0.0276(7) 0.0398(8) 0.0013(6) 0.0091(6) 0.0046(6) C26 0.0302(7) 0.0274(7) 0.0324(7) 0.0053(6) 0.0116(6) 0.0085(5) C27 0.0294(7) 0.0294(7) 0.0363(7) 0.0059(6) 0.0108(6) 0.0080(6) C28 0.0292(7) 0.0305(7) 0.0269(7) 0.0049(5) 0.0074(5) 0.0051(6) C29 0.0392(9) 0.0364(8) 0.0502(10) 0.0011(7) 0.0042(7) -0.0028(7) C30 0.0296(8) 0.0583(11) 0.0352(8) 0.0031(7) 0.0049(6) -0.0039(7) C31 0.0300(8) 0.0569(10) 0.0337(8) 0.0059(7) 0.0085(6) 0.0112(7) C32 0.0330(7) 0.0368(8) 0.0308(7) 0.0055(6) 0.0106(6) 0.0093(6) _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 1.7932(15) . ? S1 S2 2.0498(8) . ? S2 C8 1.7914(14) . ? O1 C7 1.3230(18) . ? O1 H1O 0.8401 . ? O2 C7 1.2120(18) . ? O3 C14 1.3202(18) . ? O3 H3O 0.8402 . ? O4 C14 1.2102(18) . ? N1 C19 1.336(2) . ? N1 C15 1.3458(19) . ? N2 C20 1.276(2) . ? N2 N2 1.406(3) 2_586 ? N3 C25 1.3417(19) . ? N3 C21 1.3455(18) . ? N4 C26 1.2741(19) . ? N4 N5 1.4070(17) . ? N5 C27 1.2757(19) . ? N6 C29 1.340(2) . ? N6 C28 1.3422(19) . ? C1 C6 1.393(2) . ? C1 C2 1.408(2) . ? C2 C3 1.396(2) . ? C2 C7 1.480(2) . ? C3 C4 1.375(2) . ? C3 H3 0.9500 . ? C4 C5 1.378(3) . ? C4 H4 0.9500 . ? C5 C6 1.381(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C13 1.3968(19) . ? C8 C9 1.4074(19) . ? C9 C10 1.3953(19) . ? C9 C14 1.4855(19) . ? C10 C11 1.382(2) . ? C10 H10 0.9500 . ? C11 C12 1.386(2) . ? C11 H11 0.9500 . ? C12 C13 1.386(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C15 C16 1.379(2) . ? C15 C20 1.463(2) . ? C16 C17 1.375(3) . ? C16 H16 0.9500 . ? C17 C18 1.375(3) . ? C17 H17 0.9500 . ? C18 C19 1.374(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.3887(19) . ? C21 C26 1.466(2) . ? C22 C23 1.378(2) . ? C22 H22 0.9500 . ? C23 C24 1.381(2) . ? C23 H23 0.9500 . ? C24 C25 1.384(2) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.467(2) . ? C27 H27 0.9500 . ? C28 C32 1.388(2) . ? C29 C30 1.381(3) . ? C29 H29 0.9500 . ? C30 C31 1.373(3) . ? C30 H30 0.9500 . ? C31 C32 1.379(2) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? 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 S1 S2 104.73(6) . . ? C8 S2 S1 105.32(6) . . ? C7 O1 H1O 107.4 . . ? C14 O3 H3O 109.5 . . ? C19 N1 C15 118.45(14) . . ? C20 N2 N2 111.76(16) . 2_586 ? C25 N3 C21 117.53(12) . . ? C26 N4 N5 113.05(12) . . ? C27 N5 N4 111.29(12) . . ? C29 N6 C28 116.39(14) . . ? C6 C1 C2 118.75(13) . . ? C6 C1 S1 121.96(11) . . ? C2 C1 S1 119.28(11) . . ? C3 C2 C1 119.33(14) . . ? C3 C2 C7 119.56(13) . . ? C1 C2 C7 121.10(13) . . ? C4 C3 C2 120.99(15) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.59(15) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 120.70(16) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 120.63(15) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O2 C7 O1 123.22(14) . . ? O2 C7 C2 123.03(13) . . ? O1 C7 C2 113.74(13) . . ? C13 C8 C9 118.54(12) . . ? C13 C8 S2 121.26(11) . . ? C9 C8 S2 120.19(10) . . ? C10 C9 C8 119.60(12) . . ? C10 C9 C14 120.17(12) . . ? C8 C9 C14 120.23(12) . . ? C11 C10 C9 121.31(13) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 119.00(13) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C12 C13 120.73(13) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C8 120.79(13) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? O4 C14 O3 122.97(13) . . ? O4 C14 C9 122.08(13) . . ? O3 C14 C9 114.94(12) . . ? N1 C15 C16 122.06(15) . . ? N1 C15 C20 115.39(13) . . ? C16 C15 C20 122.53(14) . . ? C17 C16 C15 118.57(16) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? C18 C17 C16 119.78(17) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C19 C18 C17 118.53(16) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? N1 C19 C18 122.59(16) . . ? N1 C19 H19 118.7 . . ? C18 C19 H19 118.7 . . ? N2 C20 C15 120.77(14) . . ? N2 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? N3 C21 C22 122.15(13) . . ? N3 C21 C26 117.12(12) . . ? C22 C21 C26 120.71(13) . . ? C23 C22 C21 119.51(13) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 118.81(13) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C23 C24 C25 118.48(14) . . ? C23 C24 H24 120.8 . . ? C25 C24 H24 120.8 . . ? N3 C25 C24 123.50(13) . . ? N3 C25 H25 118.3 . . ? C24 C25 H25 118.3 . . ? N4 C26 C21 119.15(13) . . ? N4 C26 H26 120.4 . . ? C21 C26 H26 120.4 . . ? N5 C27 C28 120.54(13) . . ? N5 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? N6 C28 C32 123.29(14) . . ? N6 C28 C27 115.29(13) . . ? C32 C28 C27 121.42(13) . . ? N6 C29 C30 123.86(16) . . ? N6 C29 H29 118.1 . . ? C30 C29 H29 118.1 . . ? C31 C30 C29 118.98(15) . . ? C31 C30 H30 120.5 . . ? C29 C30 H30 120.5 . . ? C30 C31 C32 118.50(15) . . ? C30 C31 H31 120.7 . . ? C32 C31 H31 120.7 . . ? C31 C32 C28 118.94(15) . . ? C31 C32 H32 120.5 . . ? C28 C32 H32 120.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 S1 S2 C8 85.90(7) . . . . ? C26 N4 N5 C27 177.96(13) . . . . ? S2 S1 C1 C6 -4.31(13) . . . . ? S2 S1 C1 C2 176.81(10) . . . . ? C6 C1 C2 C3 0.5(2) . . . . ? S1 C1 C2 C3 179.47(11) . . . . ? C6 C1 C2 C7 -178.40(13) . . . . ? S1 C1 C2 C7 0.52(18) . . . . ? C1 C2 C3 C4 0.2(2) . . . . ? C7 C2 C3 C4 179.19(15) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C4 C5 C6 C1 0.8(3) . . . . ? C2 C1 C6 C5 -1.1(2) . . . . ? S1 C1 C6 C5 -179.95(12) . . . . ? C3 C2 C7 O2 174.60(14) . . . . ? C1 C2 C7 O2 -6.4(2) . . . . ? C3 C2 C7 O1 -5.8(2) . . . . ? C1 C2 C7 O1 173.14(13) . . . . ? S1 S2 C8 C13 -11.60(12) . . . . ? S1 S2 C8 C9 167.81(10) . . . . ? C13 C8 C9 C10 1.6(2) . . . . ? S2 C8 C9 C10 -177.79(10) . . . . ? C13 C8 C9 C14 -178.64(12) . . . . ? S2 C8 C9 C14 1.93(18) . . . . ? C8 C9 C10 C11 -0.7(2) . . . . ? C14 C9 C10 C11 179.58(13) . . . . ? C9 C10 C11 C12 -0.5(2) . . . . ? C10 C11 C12 C13 0.7(2) . . . . ? C11 C12 C13 C8 0.2(2) . . . . ? C9 C8 C13 C12 -1.4(2) . . . . ? S2 C8 C13 C12 178.00(11) . . . . ? C10 C9 C14 O4 -174.50(15) . . . . ? C8 C9 C14 O4 5.8(2) . . . . ? C10 C9 C14 O3 4.9(2) . . . . ? C8 C9 C14 O3 -174.87(13) . . . . ? C19 N1 C15 C16 -1.4(2) . . . . ? C19 N1 C15 C20 177.40(13) . . . . ? N1 C15 C16 C17 0.5(3) . . . . ? C20 C15 C16 C17 -178.21(16) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C16 C17 C18 C19 -0.4(3) . . . . ? C15 N1 C19 C18 1.4(2) . . . . ? C17 C18 C19 N1 -0.5(3) . . . . ? N2 N2 C20 C15 179.74(15) 2_586 . . . ? N1 C15 C20 N2 -174.47(14) . . . . ? C16 C15 C20 N2 4.3(2) . . . . ? C25 N3 C21 C22 -0.4(2) . . . . ? C25 N3 C21 C26 178.35(12) . . . . ? N3 C21 C22 C23 -0.8(2) . . . . ? C26 C21 C22 C23 -179.51(13) . . . . ? C21 C22 C23 C24 1.7(2) . . . . ? C22 C23 C24 C25 -1.3(2) . . . . ? C21 N3 C25 C24 0.7(2) . . . . ? C23 C24 C25 N3 0.1(2) . . . . ? N5 N4 C26 C21 177.28(12) . . . . ? N3 C21 C26 N4 175.78(13) . . . . ? C22 C21 C26 N4 -5.5(2) . . . . ? N4 N5 C27 C28 175.90(12) . . . . ? C29 N6 C28 C32 -2.1(2) . . . . ? C29 N6 C28 C27 176.66(14) . . . . ? N5 C27 C28 N6 -162.94(14) . . . . ? N5 C27 C28 C32 15.8(2) . . . . ? C28 N6 C29 C30 0.9(3) . . . . ? N6 C29 C30 C31 0.8(3) . . . . ? C29 C30 C31 C32 -1.4(2) . . . . ? C30 C31 C32 C28 0.3(2) . . . . ? N6 C28 C32 C31 1.5(2) . . . . ? C27 C28 C32 C31 -177.16(13) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.20 _refine_diff_density_min -0.22 _refine_diff_density_rms 0.040 # Attachment '3-PA.CIF' data_3-PA _database_code_depnum_ccdc_archive 'CCDC 675040' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 O4 S2, C12 H10 N4' _chemical_formula_sum 'C26 H20 N4 O4 S2' _chemical_formula_weight 516.58 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 'P 2/n' _symmetry_space_group_name_Hall '-P 2yac ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y, -z-1/2' _cell_length_a 12.115(9) _cell_length_b 5.258(4) _cell_length_c 18.704(15) _cell_angle_alpha 90 _cell_angle_beta 92.55(2) _cell_angle_gamma 90 _cell_volume 1190.2(15) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2992 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description blade _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15652 _diffrn_reflns_av_R_equivalents 0.090 _diffrn_reflns_av_sigmaI/netI 0.053 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.4 _diffrn_reflns_theta_max 25.0 _reflns_number_total 2097 _reflns_number_gt 1938 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006' _computing_publication_material SHELXL97 _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^)+(0.0429P)^2^+3.4511P] 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 2097 _refine_ls_number_parameters 166 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.098 _refine_ls_R_factor_gt 0.088 _refine_ls_wR_factor_ref 0.174 _refine_ls_wR_factor_gt 0.169 _refine_ls_goodness_of_fit_ref 1.22 _refine_ls_restrained_S_all 1.22 _refine_ls_shift/su_max <0.001 _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 0.69037(9) -0.1094(2) 0.20932(6) 0.0308(3) Uani 1 1 d . . . O1 O 0.3409(3) -0.1071(6) 0.13923(17) 0.0338(8) Uani 1 1 d D . . H1O H 0.3268 -0.0029 0.1060 0.051 Uiso 1 1 d D . . O2 O 0.5168(3) -0.0124(6) 0.11827(16) 0.0345(8) Uani 1 1 d . . . N1 N 0.2966(3) 0.2618(7) 0.04824(19) 0.0263(8) Uani 1 1 d . . . N2 N 0.0491(3) 0.9456(7) -0.01218(18) 0.0255(8) Uani 1 1 d . . . C1 C 0.5890(4) -0.3324(8) 0.2373(2) 0.0266(10) Uani 1 1 d . . . C2 C 0.4809(4) -0.3251(9) 0.2061(2) 0.0275(10) Uani 1 1 d . . . C3 C 0.4038(4) -0.5041(9) 0.2268(2) 0.0289(10) Uani 1 1 d . . . H3 H 0.3309 -0.4997 0.2059 0.035 Uiso 1 1 calc R . . C4 C 0.4314(4) -0.6886(9) 0.2775(2) 0.0291(10) Uani 1 1 d . . . H4 H 0.3788 -0.8128 0.2901 0.035 Uiso 1 1 calc R . . C5 C 0.5363(4) -0.6898(9) 0.3094(2) 0.0305(10) Uani 1 1 d . . . H5 H 0.5549 -0.8126 0.3452 0.037 Uiso 1 1 calc R . . C6 C 0.6148(4) -0.5138(9) 0.2899(2) 0.0285(10) Uani 1 1 d . . . H6 H 0.6866 -0.5170 0.3124 0.034 Uiso 1 1 calc R . . C7 C 0.4493(4) -0.1333(8) 0.1506(2) 0.0266(10) Uani 1 1 d . . . C8 C 0.2058(4) 0.4020(8) 0.0546(2) 0.0255(10) Uani 1 1 d . . . H8 H 0.1552 0.3525 0.0894 0.031 Uiso 1 1 calc R . . C9 C 0.1807(3) 0.6154(8) 0.0135(2) 0.0237(9) Uani 1 1 d . . . C10 C 0.2548(3) 0.6877(9) -0.0382(2) 0.0270(10) Uani 1 1 d . . . H10 H 0.2411 0.8336 -0.0672 0.032 Uiso 1 1 calc R . . C11 C 0.3484(4) 0.5414(9) -0.0459(2) 0.0297(10) Uani 1 1 d . . . H11 H 0.3996 0.5842 -0.0810 0.036 Uiso 1 1 calc R . . C12 C 0.3669(4) 0.3315(9) -0.0019(2) 0.0295(10) Uani 1 1 d . . . H12 H 0.4317 0.2332 -0.0075 0.035 Uiso 1 1 calc R . . C13 C 0.0801(3) 0.7562(8) 0.0274(2) 0.0257(10) Uani 1 1 d . . . H13 H 0.0369 0.7075 0.0663 0.031 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 0.0292(6) 0.0305(6) 0.0330(7) 0.0038(5) 0.0043(5) -0.0008(5) O1 0.0307(18) 0.0353(19) 0.0352(19) 0.0079(15) -0.0033(14) -0.0003(14) O2 0.0330(18) 0.0386(19) 0.0326(18) 0.0073(15) 0.0096(14) 0.0047(15) N1 0.0262(19) 0.026(2) 0.0267(19) -0.0009(16) 0.0009(15) 0.0036(15) N2 0.0204(19) 0.032(2) 0.0244(19) -0.0033(16) 0.0029(14) 0.0037(15) C1 0.026(2) 0.031(2) 0.023(2) -0.0005(19) 0.0069(18) 0.0021(19) C2 0.032(2) 0.031(2) 0.020(2) -0.0028(19) 0.0054(18) 0.0101(19) C3 0.030(2) 0.029(2) 0.029(2) -0.004(2) 0.0072(19) 0.0033(19) C4 0.032(3) 0.032(2) 0.023(2) -0.004(2) 0.0101(19) -0.002(2) C5 0.035(3) 0.031(3) 0.026(2) 0.005(2) 0.0045(19) 0.005(2) C6 0.029(2) 0.032(2) 0.025(2) 0.0033(19) 0.0040(18) 0.0028(19) C7 0.028(2) 0.028(2) 0.023(2) -0.0054(19) 0.0004(19) 0.0049(19) C8 0.027(2) 0.028(2) 0.021(2) 0.0014(18) 0.0012(17) -0.0018(19) C9 0.022(2) 0.028(2) 0.021(2) -0.0037(18) -0.0008(17) 0.0032(18) C10 0.025(2) 0.029(2) 0.027(2) -0.0018(19) 0.0032(18) -0.0006(19) C11 0.025(2) 0.037(3) 0.027(2) -0.001(2) 0.0065(18) 0.004(2) C12 0.026(2) 0.031(3) 0.032(3) -0.007(2) 0.0016(19) 0.0053(19) C13 0.026(2) 0.028(2) 0.023(2) -0.0048(19) 0.0022(18) -0.0009(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 C1 1.793(5) . ? S1 S1 2.051(3) 4_756 ? O1 C7 1.328(5) . ? O1 H1O 0.8400 . ? O2 C7 1.217(5) . ? N1 C8 1.334(5) . ? N1 C12 1.346(6) . ? N2 C13 1.287(5) . ? N2 N2 1.413(6) 3_575 ? C1 C6 1.395(6) . ? C1 C2 1.410(6) . ? C2 C3 1.393(6) . ? C2 C7 1.486(6) . ? C3 C4 1.387(6) . ? C3 H3 0.9500 . ? C4 C5 1.379(6) . ? C4 H4 0.9500 . ? C5 C6 1.388(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.386(6) . ? C8 H8 0.9500 . ? C9 C10 1.401(6) . ? C9 C13 1.459(6) . ? C10 C11 1.383(6) . ? C10 H10 0.9500 . ? C11 C12 1.389(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 S1 S1 104.59(16) . 4_756 ? C7 O1 H1O 110.7 . . ? C8 N1 C12 117.5(4) . . ? C13 N2 N2 110.9(4) . 3_575 ? C6 C1 C2 119.0(4) . . ? C6 C1 S1 121.2(3) . . ? C2 C1 S1 119.8(3) . . ? C3 C2 C1 119.2(4) . . ? C3 C2 C7 119.9(4) . . ? C1 C2 C7 120.9(4) . . ? C4 C3 C2 121.2(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C5 C4 C3 119.3(4) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.8(4) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 120.4(4) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? O2 C7 O1 123.2(4) . . ? O2 C7 C2 122.9(4) . . ? O1 C7 C2 113.8(4) . . ? N1 C8 C9 124.0(4) . . ? N1 C8 H8 118.0 . . ? C9 C8 H8 118.0 . . ? C8 C9 C10 118.1(4) . . ? C8 C9 C13 118.4(4) . . ? C10 C9 C13 123.5(4) . . ? C11 C10 C9 118.4(4) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C10 C11 C12 119.4(4) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? N1 C12 C11 122.6(4) . . ? N1 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? N2 C13 C9 121.0(4) . . ? N2 C13 H13 119.5 . . ? C9 C13 H13 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 S1 C1 C6 -19.2(4) 4_756 . . . ? S1 S1 C1 C2 160.6(3) 4_756 . . . ? C6 C1 C2 C3 -2.0(6) . . . . ? S1 C1 C2 C3 178.1(3) . . . . ? C6 C1 C2 C7 179.3(4) . . . . ? S1 C1 C2 C7 -0.5(6) . . . . ? C1 C2 C3 C4 0.0(6) . . . . ? C7 C2 C3 C4 178.7(4) . . . . ? C2 C3 C4 C5 1.9(6) . . . . ? C3 C4 C5 C6 -1.9(6) . . . . ? C4 C5 C6 C1 -0.1(7) . . . . ? C2 C1 C6 C5 2.1(6) . . . . ? S1 C1 C6 C5 -178.1(3) . . . . ? C3 C2 C7 O2 -162.4(4) . . . . ? C1 C2 C7 O2 16.3(6) . . . . ? C3 C2 C7 O1 17.3(6) . . . . ? C1 C2 C7 O1 -164.0(4) . . . . ? C12 N1 C8 C9 -0.9(6) . . . . ? N1 C8 C9 C10 0.4(6) . . . . ? N1 C8 C9 C13 -178.1(4) . . . . ? C8 C9 C10 C11 0.6(6) . . . . ? C13 C9 C10 C11 179.0(4) . . . . ? C9 C10 C11 C12 -1.0(6) . . . . ? C8 N1 C12 C11 0.5(6) . . . . ? C10 C11 C12 N1 0.5(7) . . . . ? N2 N2 C13 C9 -179.0(4) 3_575 . . . ? C8 C9 C13 N2 -175.4(4) . . . . ? C10 C9 C13 N2 6.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.33 _refine_diff_density_min -0.36 _refine_diff_density_rms 0.081 # Attachment '4-PA.CIF' data_4-PA _database_code_depnum_ccdc_archive 'CCDC 675041' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 O4 S2, C12 H10 N4, C H2 Cl2' _chemical_formula_sum 'C27 H22 Cl2 N4 O4 S2' _chemical_formula_weight 601.53 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' Cl Cl 0.1484 0.1585 '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 c c n' _symmetry_space_group_name_Hall '-P 2ab 2ac ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 27.672(6) _cell_length_b 5.0086(10) _cell_length_c 19.107(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2648.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1838 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30.1 _exptl_crystal_description block _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.446 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.863 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 9389 _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_av_sigmaI/netI 0.019 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.6 _diffrn_reflns_theta_max 25.0 _reflns_number_total 2326 _reflns_number_gt 2173 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0823P)^2^+9.171P] 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 2326 _refine_ls_number_parameters 180 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.077 _refine_ls_R_factor_gt 0.072 _refine_ls_wR_factor_ref 0.191 _refine_ls_wR_factor_gt 0.187 _refine_ls_goodness_of_fit_ref 1.16 _refine_ls_restrained_S_all 1.16 _refine_ls_shift/su_max <0.001 _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 0.27345(3) -0.5926(2) 0.25605(5) 0.0240(3) Uani 1 1 d . . . O1 O 0.41367(10) -0.1992(6) 0.22815(15) 0.0286(7) Uani 1 1 d D . . H1O H 0.4192 -0.0737 0.2562 0.043 Uiso 1 1 d D . . O2 O 0.34111(9) -0.2263(6) 0.27873(14) 0.0249(6) Uani 1 1 d . . . N1 N 0.43114(11) 0.1831(6) 0.31782(16) 0.0232(7) Uani 1 1 d . . . N2 N 0.50009(12) 0.9001(7) 0.47413(17) 0.0259(8) Uani 1 1 d . . . C1 C 0.31642(13) -0.6686(7) 0.18926(18) 0.0189(8) Uani 1 1 d . . . C2 C 0.35932(13) -0.5195(8) 0.18462(19) 0.0199(8) Uani 1 1 d . . . C3 C 0.39237(13) -0.5780(8) 0.1318(2) 0.0235(8) Uani 1 1 d . . . H3 H 0.4215 -0.4780 0.1285 0.028 Uiso 1 1 calc R . . C4 C 0.38350(14) -0.7789(9) 0.0841(2) 0.0268(9) Uani 1 1 d . . . H4 H 0.4063 -0.8165 0.0482 0.032 Uiso 1 1 calc R . . C5 C 0.34152(14) -0.9245(9) 0.0887(2) 0.0271(9) Uani 1 1 d . . . H5 H 0.3354 -1.0639 0.0562 0.033 Uiso 1 1 calc R . . C6 C 0.30783(14) -0.8685(8) 0.1410(2) 0.0237(8) Uani 1 1 d . . . H6 H 0.2787 -0.9687 0.1435 0.028 Uiso 1 1 calc R . . C7 C 0.36985(13) -0.3013(8) 0.23490(19) 0.0208(8) Uani 1 1 d . . . C8 C 0.39590(14) 0.2835(8) 0.3575(2) 0.0243(9) Uani 1 1 d . . . H8 H 0.3643 0.2113 0.3533 0.029 Uiso 1 1 calc R . . C9 C 0.40364(14) 0.4887(8) 0.4045(2) 0.0231(8) Uani 1 1 d . . . H9 H 0.3776 0.5575 0.4315 0.028 Uiso 1 1 calc R . . C10 C 0.44978(14) 0.5931(8) 0.41194(19) 0.0214(8) Uani 1 1 d . . . C11 C 0.48652(13) 0.4879(8) 0.3707(2) 0.0223(8) Uani 1 1 d . . . H11 H 0.5186 0.5546 0.3742 0.027 Uiso 1 1 calc R . . C12 C 0.47562(14) 0.2854(8) 0.3246(2) 0.0249(9) Uani 1 1 d . . . H12 H 0.5008 0.2149 0.2963 0.030 Uiso 1 1 calc R . . C13 C 0.45809(14) 0.8056(8) 0.46319(19) 0.0229(8) Uani 1 1 d . . . H13 H 0.4315 0.8746 0.4889 0.028 Uiso 1 1 calc R . . C14 C 0.7500 0.2500 0.5836(6) 0.168(9) Uani 1 2 d S . . H14A H 0.7701 0.1357 0.6142 0.202 Uiso 0.50 1 calc PR . . H14B H 0.7299 0.3643 0.6142 0.202 Uiso 0.50 1 calc PR . . Cl1 Cl 0.71244(12) 0.0479(6) 0.53450(15) 0.1323(12) 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 S1 0.0199(5) 0.0259(6) 0.0262(5) -0.0045(4) 0.0022(4) -0.0041(4) O1 0.0220(14) 0.0307(17) 0.0330(16) -0.0099(13) 0.0012(12) -0.0093(12) O2 0.0214(13) 0.0280(15) 0.0251(14) -0.0063(12) 0.0012(11) -0.0027(12) N1 0.0253(17) 0.0227(18) 0.0217(16) 0.0002(13) -0.0037(13) -0.0033(13) N2 0.0283(17) 0.0263(18) 0.0231(16) -0.0051(14) -0.0015(14) -0.0030(15) C1 0.0167(17) 0.0197(19) 0.0201(17) 0.0010(15) -0.0015(14) 0.0038(14) C2 0.0201(18) 0.0200(19) 0.0195(18) 0.0013(15) -0.0050(14) 0.0016(15) C3 0.0199(18) 0.026(2) 0.0247(19) 0.0003(16) 0.0008(15) -0.0022(16) C4 0.027(2) 0.031(2) 0.0224(19) -0.0042(17) 0.0026(16) 0.0022(18) C5 0.029(2) 0.028(2) 0.024(2) -0.0069(17) -0.0032(16) 0.0007(17) C6 0.0219(19) 0.024(2) 0.0255(19) -0.0021(16) -0.0031(15) -0.0020(16) C7 0.0207(18) 0.022(2) 0.0201(18) 0.0035(15) -0.0038(15) 0.0005(15) C8 0.0206(18) 0.028(2) 0.0242(19) 0.0020(17) -0.0034(15) -0.0049(16) C9 0.0206(18) 0.025(2) 0.0236(19) -0.0001(16) 0.0006(15) -0.0008(16) C10 0.0262(19) 0.022(2) 0.0158(17) 0.0034(15) -0.0018(14) 0.0003(16) C11 0.0192(17) 0.025(2) 0.0225(18) -0.0005(16) -0.0016(14) -0.0055(16) C12 0.0226(19) 0.029(2) 0.0235(19) -0.0031(17) 0.0006(15) -0.0017(17) C13 0.0260(19) 0.024(2) 0.0186(18) -0.0007(16) 0.0003(15) -0.0001(16) C14 0.213(18) 0.26(2) 0.036(6) 0.000 0.000 0.092(19) Cl1 0.186(3) 0.1033(19) 0.1072(19) 0.0312(16) 0.0320(19) 0.066(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 S1 C1 1.785(4) . ? S1 S1 2.042(2) 2_535 ? O1 C7 1.323(5) . ? O1 H1O 0.8400 . ? O2 C7 1.214(5) . ? N1 C8 1.334(5) . ? N1 C12 1.340(5) . ? N2 C13 1.272(5) . ? N2 N2 1.407(7) 5_676 ? C1 C6 1.382(5) . ? C1 C2 1.405(5) . ? C2 C3 1.394(5) . ? C2 C7 1.484(5) . ? C3 C4 1.379(6) . ? C3 H3 0.9500 . ? C4 C5 1.374(6) . ? C4 H4 0.9500 . ? C5 C6 1.395(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.382(6) . ? C8 H8 0.9500 . ? C9 C10 1.387(5) . ? C9 H9 0.9500 . ? C10 C11 1.390(6) . ? C10 C13 1.465(5) . ? C11 C12 1.377(6) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 Cl1 1.727(7) . ? C14 Cl1 1.727(7) 2_655 ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 S1 S1 105.00(13) . 2_535 ? C7 O1 H1O 113.2 . . ? C8 N1 C12 118.2(3) . . ? C13 N2 N2 112.1(4) . 5_676 ? C6 C1 C2 119.2(3) . . ? C6 C1 S1 121.1(3) . . ? C2 C1 S1 119.6(3) . . ? C3 C2 C1 119.2(3) . . ? C3 C2 C7 119.7(3) . . ? C1 C2 C7 121.1(3) . . ? C4 C3 C2 121.0(4) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 119.7(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.3(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 120.5(4) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? O2 C7 O1 123.2(4) . . ? O2 C7 C2 123.1(3) . . ? O1 C7 C2 113.7(3) . . ? N1 C8 C9 122.5(3) . . ? N1 C8 H8 118.8 . . ? C9 C8 H8 118.8 . . ? C8 C9 C10 119.3(4) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C9 C10 C11 118.2(4) . . ? C9 C10 C13 119.1(3) . . ? C11 C10 C13 122.7(3) . . ? C12 C11 C10 118.8(3) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? N1 C12 C11 123.0(4) . . ? N1 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? N2 C13 C10 121.6(4) . . ? N2 C13 H13 119.2 . . ? C10 C13 H13 119.2 . . ? Cl1 C14 Cl1 114.3(7) . 2_655 ? Cl1 C14 H14A 108.7 . . ? Cl1 C14 H14A 108.7 2_655 . ? Cl1 C14 H14B 108.7 . . ? Cl1 C14 H14B 108.7 2_655 . ? H14A C14 H14B 107.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 S1 C1 C6 13.9(3) 2_535 . . . ? S1 S1 C1 C2 -167.4(3) 2_535 . . . ? C6 C1 C2 C3 -0.5(5) . . . . ? S1 C1 C2 C3 -179.2(3) . . . . ? C6 C1 C2 C7 179.4(3) . . . . ? S1 C1 C2 C7 0.7(5) . . . . ? C1 C2 C3 C4 0.2(6) . . . . ? C7 C2 C3 C4 -179.7(4) . . . . ? C2 C3 C4 C5 -0.2(6) . . . . ? C3 C4 C5 C6 0.5(6) . . . . ? C2 C1 C6 C5 0.8(6) . . . . ? S1 C1 C6 C5 179.5(3) . . . . ? C4 C5 C6 C1 -0.8(6) . . . . ? C3 C2 C7 O2 174.2(4) . . . . ? C1 C2 C7 O2 -5.7(6) . . . . ? C3 C2 C7 O1 -6.8(5) . . . . ? C1 C2 C7 O1 173.3(3) . . . . ? C12 N1 C8 C9 0.5(6) . . . . ? N1 C8 C9 C10 -0.9(6) . . . . ? C8 C9 C10 C11 0.7(6) . . . . ? C8 C9 C10 C13 -178.4(4) . . . . ? C9 C10 C11 C12 -0.1(6) . . . . ? C13 C10 C11 C12 179.0(4) . . . . ? C8 N1 C12 C11 0.2(6) . . . . ? C10 C11 C12 N1 -0.4(6) . . . . ? N2 N2 C13 C10 -179.4(4) 5_676 . . . ? C9 C10 C13 N2 176.9(4) . . . . ? C11 C10 C13 N2 -2.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.77 _refine_diff_density_min -1.17 # 0.91 A from CL1 _refine_diff_density_rms 0.091