# Electronic Supplementary Material (ESI) for CrystEngComm # 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_shelx #TrackingRef 'crystal1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 N4 O7 S' _chemical_formula_weight 472.48 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.924(8) _cell_length_b 9.781(6) _cell_length_c 22.976(16) _cell_angle_alpha 90.00 _cell_angle_beta 102.64(3) _cell_angle_gamma 90.00 _cell_volume 2176(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17978 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0844 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.01 _reflns_number_total 5195 _reflns_number_gt 2742 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0717P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5195 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0878 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1574 _refine_ls_wR_factor_gt 0.1228 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _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 0.75193(5) 0.41328(6) -0.11539(3) 0.04227(19) Uani 1 1 d . . . O1 O 0.74232(16) 0.43441(18) -0.05431(8) 0.0555(5) Uani 1 1 d . . . O2 O 0.85078(15) 0.5070(2) -0.13195(9) 0.0657(6) Uani 1 1 d . . . O3 O 0.7778(2) 0.27370(19) -0.12851(10) 0.0805(7) Uani 1 1 d . . . C1 C 0.5895(2) 0.4552(2) -0.16062(10) 0.0355(5) Uani 1 1 d . . . C2 C 0.5419(2) 0.3873(2) -0.21394(11) 0.0456(6) Uani 1 1 d . . . H2 H 0.5942 0.3175 -0.2254 0.055 Uiso 1 1 calc R . . C3 C 0.4180(2) 0.4228(2) -0.24996(11) 0.0478(6) Uani 1 1 d . . . H3 H 0.3870 0.3774 -0.2860 0.057 Uiso 1 1 calc R . . C4 C 0.3384(2) 0.5257(2) -0.23328(10) 0.0395(5) Uani 1 1 d . . . O4 O 0.21620(16) 0.55669(19) -0.26982(8) 0.0577(5) Uani 1 1 d . . . H4 H 0.199(4) 0.645(4) -0.2495(18) 0.141(16) Uiso 1 1 d . . . C5 C 0.3854(2) 0.5960(2) -0.17955(9) 0.0343(5) Uani 1 1 d . . . O5 O 0.34194(17) 0.76301(18) -0.11130(8) 0.0593(5) Uani 1 1 d . . . O6 O 0.18909(17) 0.73673(19) -0.19526(9) 0.0672(6) Uani 1 1 d . . . C6 C 0.51141(19) 0.5584(2) -0.14395(10) 0.0354(5) Uani 1 1 d . . . H6 H 0.5439 0.6038 -0.1081 0.042 Uiso 1 1 calc R . . C7 C 0.2999(2) 0.7049(3) -0.16067(11) 0.0442(6) Uani 1 1 d . . . C8 C 0.1523(2) 1.3220(3) -0.15692(10) 0.0438(6) Uani 1 1 d . . . C9 C 0.2797(2) 1.2733(2) -0.12724(12) 0.0448(6) Uani 1 1 d . . . N1 N 0.31115(19) 1.3424(2) -0.07388(9) 0.0502(5) Uani 1 1 d . . . H1 H 0.3859 1.3328 -0.0471 0.060 Uiso 1 1 d R . . C10 C 0.2102(2) 1.4249(3) -0.07060(11) 0.0484(6) Uani 1 1 d . . . H10 H 0.2071 1.4811 -0.0383 0.058 Uiso 1 1 calc R . . N2 N 0.11349(18) 1.4172(2) -0.11954(9) 0.0465(5) Uani 1 1 d . . . H2N H 0.0382 1.4637 -0.1271 0.056 Uiso 1 1 d R . . C11 C 0.0851(3) 1.2766(4) -0.21219(13) 0.0689(9) Uani 1 1 d . . . H11 H -0.0002 1.3114 -0.2315 0.083 Uiso 1 1 calc R . . C12 C 0.1497(5) 1.1792(5) -0.23664(18) 0.1008(14) Uani 1 1 d . . . H12 H 0.1079 1.1463 -0.2742 0.121 Uiso 1 1 calc R . . C13 C 0.2751(5) 1.1257(4) -0.2086(2) 0.0999(14) Uani 1 1 d . . . H13 H 0.3140 1.0566 -0.2273 0.120 Uiso 1 1 calc R . . C14 C 0.3463(3) 1.1721(3) -0.15262(19) 0.0798(10) Uani 1 1 d . . . H14 H 0.4321 1.1376 -0.1338 0.096 Uiso 1 1 calc R . . C15 C 0.1773(2) 1.0198(2) -0.04022(12) 0.0441(6) Uani 1 1 d . . . C16 C 0.0650(2) 1.1083(2) -0.04540(12) 0.0451(6) Uani 1 1 d . . . N3 N -0.02020(19) 1.0794(2) -0.09953(10) 0.0497(6) Uani 1 1 d . . . H3N H -0.0982 1.1181 -0.1139 0.060 Uiso 1 1 d R . . C17 C 0.0362(2) 0.9819(3) -0.12564(12) 0.0491(6) Uani 1 1 d . . . H17 H -0.0020 0.9455 -0.1630 0.059 Uiso 1 1 calc R . . N4 N 0.15431(18) 0.9429(2) -0.09140(10) 0.0475(5) Uani 1 1 d . . . H4N H 0.2078 0.8802 -0.0997 0.057 Uiso 1 1 d R . . C18 C 0.2856(3) 1.0229(3) 0.00932(13) 0.0603(7) Uani 1 1 d . . . H18 H 0.3611 0.9646 0.0132 0.072 Uiso 1 1 calc R . . C19 C 0.2754(4) 1.1168(3) 0.05231(15) 0.0770(9) Uani 1 1 d . . . H19 H 0.3467 1.1230 0.0860 0.092 Uiso 1 1 calc R . . C20 C 0.1615(4) 1.2035(3) 0.04723(16) 0.0750(9) Uani 1 1 d . . . H20 H 0.1586 1.2646 0.0780 0.090 Uiso 1 1 calc R . . C21 C 0.0550(3) 1.2014(3) -0.00128(15) 0.0628(8) Uani 1 1 d . . . H21 H -0.0205 1.2594 -0.0046 0.075 Uiso 1 1 calc R . . O1W O 0.4465(2) 0.6992(3) 0.00274(12) 0.0863(9) Uani 1 1 d . . . H1W H 0.386(3) 0.673(4) 0.0163(16) 0.095(14) Uiso 1 1 d . . . H2W H 0.416(3) 0.718(3) -0.0348(15) 0.064(9) 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 S1 0.0351(3) 0.0496(4) 0.0402(4) -0.0002(3) 0.0043(2) 0.0138(2) O1 0.0456(9) 0.0842(14) 0.0338(10) 0.0012(9) 0.0020(7) 0.0112(8) O2 0.0321(9) 0.0912(14) 0.0749(15) 0.0198(11) 0.0140(8) 0.0056(9) O3 0.0804(13) 0.0592(13) 0.0856(17) -0.0213(11) -0.0174(11) 0.0416(10) C1 0.0335(11) 0.0383(12) 0.0345(13) 0.0009(10) 0.0071(8) 0.0043(9) C2 0.0459(13) 0.0472(14) 0.0438(15) -0.0062(12) 0.0102(10) 0.0084(10) C3 0.0543(14) 0.0526(15) 0.0335(14) -0.0087(11) 0.0030(10) -0.0031(11) C4 0.0369(12) 0.0443(13) 0.0344(13) 0.0046(10) 0.0012(9) -0.0006(10) O4 0.0453(10) 0.0667(12) 0.0483(12) 0.0006(10) -0.0179(8) 0.0029(9) C5 0.0327(11) 0.0384(12) 0.0310(12) 0.0033(9) 0.0052(8) 0.0032(9) O5 0.0590(11) 0.0681(13) 0.0449(12) -0.0087(9) -0.0014(8) 0.0331(9) O6 0.0498(11) 0.0798(13) 0.0606(14) -0.0044(10) -0.0128(9) 0.0313(9) C6 0.0343(11) 0.0412(13) 0.0287(12) -0.0015(9) 0.0028(8) 0.0041(9) C7 0.0363(12) 0.0506(14) 0.0426(15) 0.0063(12) 0.0016(10) 0.0117(10) C8 0.0372(12) 0.0611(16) 0.0320(13) -0.0006(12) 0.0053(9) -0.0146(10) C9 0.0397(13) 0.0508(15) 0.0461(16) 0.0035(12) 0.0143(10) -0.0037(10) N1 0.0329(10) 0.0713(15) 0.0411(13) 0.0089(11) -0.0031(8) -0.0058(10) C10 0.0488(14) 0.0597(17) 0.0380(15) -0.0049(12) 0.0123(11) -0.0109(12) N2 0.0343(10) 0.0589(14) 0.0461(13) 0.0051(10) 0.0083(8) 0.0029(9) C11 0.0707(19) 0.097(2) 0.0367(16) -0.0051(16) 0.0066(13) -0.0406(17) C12 0.131(3) 0.110(3) 0.070(3) -0.035(2) 0.041(3) -0.063(3) C13 0.139(4) 0.067(2) 0.121(4) -0.036(3) 0.086(3) -0.019(2) C14 0.070(2) 0.069(2) 0.114(3) 0.012(2) 0.052(2) 0.0097(16) C15 0.0426(13) 0.0419(13) 0.0501(16) 0.0071(12) 0.0151(10) 0.0056(10) C16 0.0465(13) 0.0391(13) 0.0559(17) 0.0090(12) 0.0250(11) 0.0048(10) N3 0.0408(11) 0.0473(13) 0.0623(16) 0.0119(11) 0.0145(10) 0.0134(9) C17 0.0484(14) 0.0503(15) 0.0477(16) 0.0075(12) 0.0086(11) 0.0032(11) N4 0.0426(11) 0.0496(12) 0.0499(14) 0.0005(10) 0.0090(9) 0.0141(9) C18 0.0553(16) 0.0624(18) 0.060(2) 0.0073(15) 0.0065(13) 0.0045(13) C19 0.098(2) 0.078(2) 0.052(2) 0.0009(18) 0.0092(16) -0.0214(19) C20 0.116(3) 0.0494(18) 0.071(2) -0.0093(16) 0.046(2) -0.0141(18) C21 0.077(2) 0.0447(16) 0.078(2) 0.0039(16) 0.0411(17) 0.0035(13) O1W 0.0449(12) 0.155(2) 0.0513(15) 0.0342(15) -0.0053(10) -0.0044(13) _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 O3 1.4333(19) . ? S1 O1 1.442(2) . ? S1 O2 1.4530(19) . ? S1 C1 1.764(2) . ? C1 C6 1.377(3) . ? C1 C2 1.383(3) . ? C2 C3 1.368(3) . ? C2 H2 0.9300 . ? C3 C4 1.384(3) . ? C3 H3 0.9300 . ? C4 O4 1.350(3) . ? C4 C5 1.401(3) . ? O4 H4 1.02(4) . ? C5 C6 1.386(3) . ? C5 C7 1.484(3) . ? O5 C7 1.256(3) . ? O6 C7 1.247(3) . ? C6 H6 0.9300 . ? C8 C11 1.372(4) . ? C8 N2 1.378(3) . ? C8 C9 1.383(3) . ? C9 N1 1.375(3) . ? C9 C14 1.388(4) . ? N1 C10 1.301(3) . ? N1 H1 0.8600 . ? C10 N2 1.311(3) . ? C10 H10 0.9300 . ? N2 H2N 0.8592 . ? C11 C12 1.339(5) . ? C11 H11 0.9300 . ? C12 C13 1.373(6) . ? C12 H12 0.9300 . ? C13 C14 1.400(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 N4 1.372(3) . ? C15 C18 1.384(4) . ? C15 C16 1.395(3) . ? C16 N3 1.372(3) . ? C16 C21 1.383(4) . ? N3 C17 1.315(3) . ? N3 H3N 0.8600 . ? C17 N4 1.317(3) . ? C17 H17 0.9300 . ? N4 H4N 0.8594 . ? C18 C19 1.368(4) . ? C18 H18 0.9300 . ? C19 C20 1.398(5) . ? C19 H19 0.9300 . ? C20 C21 1.358(5) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? O1W H1W 0.78(3) . ? O1W H2W 0.87(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 O3 S1 O1 113.22(13) . . ? O3 S1 O2 112.55(14) . . ? O1 S1 O2 110.90(12) . . ? O3 S1 C1 106.26(11) . . ? O1 S1 C1 107.07(11) . . ? O2 S1 C1 106.34(11) . . ? C6 C1 C2 119.6(2) . . ? C6 C1 S1 120.24(17) . . ? C2 C1 S1 120.10(17) . . ? C3 C2 C1 120.1(2) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 120.6(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? O4 C4 C3 118.7(2) . . ? O4 C4 C5 121.2(2) . . ? C3 C4 C5 120.07(19) . . ? C4 O4 H4 97(2) . . ? C6 C5 C4 118.2(2) . . ? C6 C5 C7 121.2(2) . . ? C4 C5 C7 120.58(19) . . ? C1 C6 C5 121.4(2) . . ? C1 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? O6 C7 O5 122.3(2) . . ? O6 C7 C5 118.3(2) . . ? O5 C7 C5 119.41(19) . . ? C11 C8 N2 130.6(3) . . ? C11 C8 C9 123.4(3) . . ? N2 C8 C9 106.0(2) . . ? N1 C9 C8 106.0(2) . . ? N1 C9 C14 133.6(3) . . ? C8 C9 C14 120.5(3) . . ? C10 N1 C9 109.21(19) . . ? C10 N1 H1 125.5 . . ? C9 N1 H1 125.3 . . ? N1 C10 N2 110.0(2) . . ? N1 C10 H10 125.0 . . ? N2 C10 H10 125.0 . . ? C10 N2 C8 108.8(2) . . ? C10 N2 H2N 125.7 . . ? C8 N2 H2N 125.5 . . ? C12 C11 C8 116.0(3) . . ? C12 C11 H11 122.0 . . ? C8 C11 H11 122.0 . . ? C11 C12 C13 122.8(4) . . ? C11 C12 H12 118.6 . . ? C13 C12 H12 118.6 . . ? C12 C13 C14 122.1(3) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C9 C14 C13 115.2(3) . . ? C9 C14 H14 122.4 . . ? C13 C14 H14 122.4 . . ? N4 C15 C18 132.1(2) . . ? N4 C15 C16 106.7(2) . . ? C18 C15 C16 121.2(3) . . ? N3 C16 C21 132.2(2) . . ? N3 C16 C15 105.8(2) . . ? C21 C16 C15 122.0(3) . . ? C17 N3 C16 108.9(2) . . ? C17 N3 H3N 125.6 . . ? C16 N3 H3N 125.5 . . ? N3 C17 N4 110.4(2) . . ? N3 C17 H17 124.8 . . ? N4 C17 H17 124.8 . . ? C17 N4 C15 108.2(2) . . ? C17 N4 H4N 125.9 . . ? C15 N4 H4N 125.8 . . ? C19 C18 C15 116.2(3) . . ? C19 C18 H18 121.9 . . ? C15 C18 H18 121.9 . . ? C18 C19 C20 122.2(3) . . ? C18 C19 H19 118.9 . . ? C20 C19 H19 118.9 . . ? C21 C20 C19 121.9(3) . . ? C21 C20 H20 119.0 . . ? C19 C20 H20 119.0 . . ? C20 C21 C16 116.4(3) . . ? C20 C21 H21 121.8 . . ? C16 C21 H21 121.8 . . ? H1W O1W H2W 110(3) . . ? 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 O3 S1 C1 C6 155.3(2) . . . . ? O1 S1 C1 C6 34.0(2) . . . . ? O2 S1 C1 C6 -84.6(2) . . . . ? O3 S1 C1 C2 -26.7(2) . . . . ? O1 S1 C1 C2 -148.0(2) . . . . ? O2 S1 C1 C2 93.4(2) . . . . ? C6 C1 C2 C3 0.1(4) . . . . ? S1 C1 C2 C3 -177.88(19) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 O4 -179.4(2) . . . . ? C2 C3 C4 C5 1.0(4) . . . . ? O4 C4 C5 C6 179.6(2) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? O4 C4 C5 C7 1.5(3) . . . . ? C3 C4 C5 C7 -179.0(2) . . . . ? C2 C1 C6 C5 0.1(3) . . . . ? S1 C1 C6 C5 178.06(17) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C7 C5 C6 C1 178.4(2) . . . . ? C6 C5 C7 O6 178.2(2) . . . . ? C4 C5 C7 O6 -3.7(4) . . . . ? C6 C5 C7 O5 -0.7(4) . . . . ? C4 C5 C7 O5 177.4(2) . . . . ? C11 C8 C9 N1 -179.6(2) . . . . ? N2 C8 C9 N1 -0.4(3) . . . . ? C11 C8 C9 C14 -0.8(4) . . . . ? N2 C8 C9 C14 178.4(2) . . . . ? C8 C9 N1 C10 1.1(3) . . . . ? C14 C9 N1 C10 -177.5(3) . . . . ? C9 N1 C10 N2 -1.3(3) . . . . ? N1 C10 N2 C8 1.1(3) . . . . ? C11 C8 N2 C10 178.7(3) . . . . ? C9 C8 N2 C10 -0.3(3) . . . . ? N2 C8 C11 C12 -178.3(3) . . . . ? C9 C8 C11 C12 0.6(4) . . . . ? C8 C11 C12 C13 0.6(5) . . . . ? C11 C12 C13 C14 -1.6(6) . . . . ? N1 C9 C14 C13 178.2(3) . . . . ? C8 C9 C14 C13 -0.2(4) . . . . ? C12 C13 C14 C9 1.4(5) . . . . ? N4 C15 C16 N3 0.3(3) . . . . ? C18 C15 C16 N3 179.0(2) . . . . ? N4 C15 C16 C21 -179.8(2) . . . . ? C18 C15 C16 C21 -1.1(4) . . . . ? C21 C16 N3 C17 179.5(3) . . . . ? C15 C16 N3 C17 -0.6(3) . . . . ? C16 N3 C17 N4 0.7(3) . . . . ? N3 C17 N4 C15 -0.5(3) . . . . ? C18 C15 N4 C17 -178.4(3) . . . . ? C16 C15 N4 C17 0.1(3) . . . . ? N4 C15 C18 C19 178.5(3) . . . . ? C16 C15 C18 C19 0.2(4) . . . . ? C15 C18 C19 C20 0.9(4) . . . . ? C18 C19 C20 C21 -1.1(5) . . . . ? C19 C20 C21 C16 0.2(5) . . . . ? N3 C16 C21 C20 -179.2(3) . . . . ? C15 C16 C21 C20 0.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.323 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 921356' ####################################################################### # # 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_mono_2 #TrackingRef 'crystal2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 N4 O6 S' _chemical_formula_weight 454.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 21.4632(18) _cell_length_b 5.7527(5) _cell_length_c 18.1385(15) _cell_angle_alpha 90.00 _cell_angle_beta 114.205(6) _cell_angle_gamma 90.00 _cell_volume 2042.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 1.838 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8609 _exptl_absorpt_correction_T_max 0.9334 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10384 _diffrn_reflns_av_R_equivalents 0.0713 _diffrn_reflns_av_sigmaI/netI 0.1227 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 66.61 _reflns_number_total 3397 _reflns_number_gt 1715 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0672P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3397 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1382 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1629 _refine_ls_wR_factor_gt 0.1315 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 0.66463(5) 0.00361(18) 0.26457(6) 0.0510(3) Uani 1 1 d . . . O4 O 0.89546(14) 0.0136(5) 0.58537(16) 0.0659(8) Uani 1 1 d . . . H4A H 0.885(2) 0.146(7) 0.610(3) 0.099 Uiso 1 1 d . . . O1 O 0.65477(13) -0.2363(4) 0.24064(16) 0.0744(9) Uani 1 1 d . . . O2 O 0.68497(14) 0.1448(5) 0.21241(15) 0.0823(9) Uani 1 1 d . . . O3 O 0.60672(12) 0.1027(4) 0.27569(14) 0.0655(8) Uani 1 1 d . . . O5 O 0.74644(14) 0.5215(4) 0.53240(15) 0.0609(8) Uani 1 1 d . . . O6 O 0.84529(14) 0.3778(5) 0.61832(16) 0.0645(8) Uani 1 1 d . . . N1 N 0.37226(15) 0.1880(6) 0.07828(18) 0.0532(8) Uani 1 1 d . . . H1 H 0.3306 0.1442 0.0524 0.064 Uiso 1 1 calc R . . N2 N 0.47679(16) 0.1943(6) 0.16578(18) 0.0548(9) Uani 1 1 d . . . H2 H 0.5140 0.1564 0.2060 0.066 Uiso 1 1 calc R . . N3 N 0.16450(19) 0.2565(7) 0.2967(2) 0.0594(10) Uani 1 1 d . . . C12 C 0.4877(2) 0.7236(7) 0.0572(3) 0.0670(12) Uani 1 1 d . . . H12 H 0.5161 0.8433 0.0553 0.080 Uiso 1 1 calc R . . C13 C 0.4200(3) 0.7195(7) 0.0001(3) 0.0656(12) Uani 1 1 d . . . H13 H 0.4049 0.8350 -0.0392 0.079 Uiso 1 1 calc R . . C14 C 0.3755(2) 0.5500(7) 0.0004(2) 0.0575(11) Uani 1 1 d . . . H14 H 0.3303 0.5476 -0.0372 0.069 Uiso 1 1 calc R . . C9 C 0.4016(2) 0.3817(6) 0.0601(2) 0.0467(10) Uani 1 1 d . . . C10 C 0.4186(2) 0.0804(7) 0.1420(2) 0.0547(10) Uani 1 1 d . . . H10 H 0.4112 -0.0536 0.1660 0.066 Uiso 1 1 calc R . . C11 C 0.5137(2) 0.5568(7) 0.1162(3) 0.0606(12) Uani 1 1 d . . . H11 H 0.5589 0.5598 0.1540 0.073 Uiso 1 1 calc R . . C8 C 0.4689(2) 0.3843(7) 0.1161(2) 0.0487(10) Uani 1 1 d . . . C4 C 0.8419(2) 0.0207(7) 0.5126(2) 0.0484(10) Uani 1 1 d . . . C5 C 0.79247(18) 0.1925(6) 0.4915(2) 0.0432(9) Uani 1 1 d . . . C6 C 0.73963(18) 0.1864(6) 0.4146(2) 0.0486(10) Uani 1 1 d . . . H6A H 0.7077 0.3059 0.3989 0.058 Uiso 1 1 calc R . . C1 C 0.73306(18) 0.0083(6) 0.3606(2) 0.0420(9) Uani 1 1 d . . . C7 C 0.7939(2) 0.3783(7) 0.5495(2) 0.0539(10) Uani 1 1 d . . . C3 C 0.8360(2) -0.1596(7) 0.4592(2) 0.0557(11) Uani 1 1 d . . . H3A H 0.8687 -0.2769 0.4741 0.067 Uiso 1 1 calc R . . C2 C 0.7821(2) -0.1657(7) 0.3845(2) 0.0528(10) Uani 1 1 d . . . H2A H 0.7784 -0.2882 0.3495 0.063 Uiso 1 1 calc R . . C17 C 0.2242(2) 0.1619(8) 0.3150(2) 0.0594(11) Uani 1 1 d . . . H17 H 0.2652 0.2223 0.3523 0.071 Uiso 1 1 calc R . . C15 C 0.1151(2) 0.1200(7) 0.2388(2) 0.0546(11) Uani 1 1 d . . . C18 C 0.0452(2) 0.1428(8) 0.1997(3) 0.0791(14) Uani 1 1 d . . . H18 H 0.0222 0.2676 0.2096 0.095 Uiso 1 1 calc R . . C19 C 0.0114(3) -0.0287(9) 0.1453(3) 0.0966(17) Uani 1 1 d . . . H19 H -0.0360 -0.0231 0.1189 0.116 Uiso 1 1 calc R . . C16 C 0.1503(2) -0.0638(7) 0.2241(2) 0.0527(10) Uani 1 1 d . . . C21 C 0.1158(2) -0.2353(7) 0.1678(3) 0.0693(13) Uani 1 1 d . . . H21 H 0.1388 -0.3593 0.1573 0.083 Uiso 1 1 calc R . . C20 C 0.0468(3) -0.2117(8) 0.1290(3) 0.0883(15) Uani 1 1 d . . . H20 H 0.0223 -0.3211 0.0902 0.106 Uiso 1 1 calc R . . N4 N 0.21841(18) -0.0323(6) 0.2732(2) 0.0583(9) Uani 1 1 d . . . H4 H 0.2513 -0.1225 0.2763 0.070 Uiso 1 1 calc R . . H3 H 0.161(2) 0.401(7) 0.323(3) 0.084(15) 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 S1 0.0419(6) 0.0642(8) 0.0450(6) -0.0084(5) 0.0159(5) -0.0071(5) O4 0.0544(19) 0.076(2) 0.0507(18) 0.0020(15) 0.0045(15) 0.0150(16) O1 0.0623(19) 0.0577(19) 0.083(2) -0.0307(16) 0.0094(16) -0.0090(15) O2 0.073(2) 0.119(3) 0.0482(16) 0.0110(17) 0.0179(16) -0.0340(18) O3 0.0388(17) 0.097(2) 0.0536(16) -0.0061(15) 0.0116(14) 0.0134(15) O5 0.0471(18) 0.0702(19) 0.0547(17) -0.0120(14) 0.0102(14) 0.0090(15) O6 0.0541(18) 0.073(2) 0.0496(17) -0.0089(15) 0.0039(15) 0.0073(16) N1 0.035(2) 0.066(2) 0.052(2) -0.0014(18) 0.0115(17) 0.0032(18) N2 0.045(2) 0.064(2) 0.052(2) -0.0050(19) 0.0167(17) 0.0028(19) N3 0.057(3) 0.067(3) 0.052(2) -0.010(2) 0.020(2) 0.000(2) C12 0.069(3) 0.069(3) 0.074(3) -0.014(3) 0.040(3) -0.015(3) C13 0.084(4) 0.058(3) 0.064(3) -0.004(2) 0.039(3) -0.005(3) C14 0.058(3) 0.061(3) 0.056(3) 0.000(2) 0.026(2) 0.006(2) C9 0.043(3) 0.046(3) 0.056(3) -0.007(2) 0.025(2) -0.005(2) C10 0.045(3) 0.065(3) 0.050(2) 0.000(2) 0.015(2) -0.003(2) C11 0.052(3) 0.071(3) 0.061(3) -0.020(3) 0.024(2) -0.009(3) C8 0.044(3) 0.057(3) 0.049(2) -0.008(2) 0.022(2) 0.000(2) C4 0.046(3) 0.056(3) 0.041(2) 0.000(2) 0.015(2) -0.001(2) C5 0.035(2) 0.052(2) 0.039(2) -0.0002(19) 0.0111(18) 0.006(2) C6 0.041(2) 0.055(3) 0.043(2) 0.003(2) 0.0109(19) 0.002(2) C1 0.031(2) 0.052(2) 0.041(2) -0.003(2) 0.0119(18) -0.0038(19) C7 0.045(3) 0.065(3) 0.046(3) 0.001(2) 0.013(2) 0.001(2) C3 0.053(3) 0.056(3) 0.052(3) 0.010(2) 0.016(2) 0.012(2) C2 0.056(3) 0.052(3) 0.051(2) -0.005(2) 0.021(2) 0.007(2) C17 0.057(3) 0.070(3) 0.047(3) 0.000(2) 0.017(2) -0.006(3) C15 0.055(3) 0.061(3) 0.050(3) -0.006(2) 0.023(2) -0.002(3) C18 0.052(3) 0.086(4) 0.093(3) -0.023(3) 0.024(3) 0.008(3) C19 0.049(3) 0.110(4) 0.113(4) -0.042(4) 0.014(3) -0.007(3) C16 0.050(3) 0.060(3) 0.053(3) 0.003(2) 0.026(2) 0.002(2) C21 0.059(3) 0.066(3) 0.077(3) -0.015(3) 0.023(3) 0.003(3) C20 0.064(4) 0.085(4) 0.102(4) -0.038(3) 0.021(3) -0.012(3) N4 0.050(2) 0.067(2) 0.061(2) 0.008(2) 0.025(2) 0.0114(19) _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 O1 1.436(3) . ? S1 O2 1.444(2) . ? S1 O3 1.455(2) . ? S1 C1 1.759(4) . ? O4 C4 1.350(4) . ? O4 H4A 0.96(4) . ? O5 C7 1.246(4) . ? O6 C7 1.283(4) . ? N1 C10 1.329(4) . ? N1 C9 1.385(4) . ? N1 H1 0.8600 . ? N2 C10 1.317(4) . ? N2 C8 1.382(4) . ? N2 H2 0.8600 . ? N3 C17 1.304(5) . ? N3 C15 1.389(5) . ? N3 H3 0.98(4) . ? C12 C11 1.374(5) . ? C12 C13 1.396(5) . ? C12 H12 0.9300 . ? C13 C14 1.368(5) . ? C13 H13 0.9300 . ? C14 C9 1.388(5) . ? C14 H14 0.9300 . ? C9 C8 1.383(5) . ? C10 H10 0.9300 . ? C11 C8 1.382(5) . ? C11 H11 0.9300 . ? C4 C5 1.384(5) . ? C4 C3 1.389(5) . ? C5 C6 1.392(4) . ? C5 C7 1.491(5) . ? C6 C1 1.384(4) . ? C6 H6A 0.9300 . ? C1 C2 1.386(5) . ? C3 C2 1.375(5) . ? C3 H3A 0.9300 . ? C2 H2A 0.9300 . ? C17 N4 1.327(4) . ? C17 H17 0.9300 . ? C15 C18 1.378(5) . ? C15 C16 1.387(5) . ? C18 C19 1.373(5) . ? C18 H18 0.9300 . ? C19 C20 1.399(6) . ? C19 H19 0.9300 . ? C16 N4 1.378(5) . ? C16 C21 1.394(5) . ? C21 C20 1.361(6) . ? C21 H21 0.9300 . ? C20 H20 0.9300 . ? N4 H4 0.8600 . ? 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 O1 S1 O2 112.91(17) . . ? O1 S1 O3 112.96(17) . . ? O2 S1 O3 112.06(17) . . ? O1 S1 C1 105.89(17) . . ? O2 S1 C1 106.65(15) . . ? O3 S1 C1 105.70(16) . . ? C4 O4 H4A 99(3) . . ? C10 N1 C9 109.3(3) . . ? C10 N1 H1 125.4 . . ? C9 N1 H1 125.4 . . ? C10 N2 C8 109.5(3) . . ? C10 N2 H2 125.3 . . ? C8 N2 H2 125.3 . . ? C17 N3 C15 108.8(4) . . ? C17 N3 H3 120(2) . . ? C15 N3 H3 131(2) . . ? C11 C12 C13 122.3(4) . . ? C11 C12 H12 118.9 . . ? C13 C12 H12 118.9 . . ? C14 C13 C12 121.7(4) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C9 116.2(4) . . ? C13 C14 H14 121.9 . . ? C9 C14 H14 121.9 . . ? C8 C9 N1 105.9(3) . . ? C8 C9 C14 122.1(4) . . ? N1 C9 C14 132.0(4) . . ? N2 C10 N1 108.9(4) . . ? N2 C10 H10 125.5 . . ? N1 C10 H10 125.5 . . ? C12 C11 C8 116.1(4) . . ? C12 C11 H11 122.0 . . ? C8 C11 H11 122.0 . . ? C11 C8 N2 131.9(4) . . ? C11 C8 C9 121.7(4) . . ? N2 C8 C9 106.4(3) . . ? O4 C4 C5 122.7(3) . . ? O4 C4 C3 117.2(4) . . ? C5 C4 C3 120.1(4) . . ? C4 C5 C6 118.4(4) . . ? C4 C5 C7 121.7(3) . . ? C6 C5 C7 119.9(3) . . ? C1 C6 C5 122.2(4) . . ? C1 C6 H6A 118.9 . . ? C5 C6 H6A 118.9 . . ? C6 C1 C2 118.0(3) . . ? C6 C1 S1 120.9(3) . . ? C2 C1 S1 121.1(3) . . ? O5 C7 O6 122.2(4) . . ? O5 C7 C5 121.3(4) . . ? O6 C7 C5 116.4(4) . . ? C2 C3 C4 120.3(4) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C3 C2 C1 120.9(4) . . ? C3 C2 H2A 119.5 . . ? C1 C2 H2A 119.5 . . ? N3 C17 N4 110.7(4) . . ? N3 C17 H17 124.6 . . ? N4 C17 H17 124.6 . . ? C18 C15 C16 122.5(4) . . ? C18 C15 N3 131.9(4) . . ? C16 C15 N3 105.7(4) . . ? C19 C18 C15 116.4(4) . . ? C19 C18 H18 121.8 . . ? C15 C18 H18 121.8 . . ? C18 C19 C20 121.3(4) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? N4 C16 C15 107.0(4) . . ? N4 C16 C21 132.1(4) . . ? C15 C16 C21 120.9(4) . . ? C20 C21 C16 116.5(4) . . ? C20 C21 H21 121.8 . . ? C16 C21 H21 121.8 . . ? C21 C20 C19 122.4(4) . . ? C21 C20 H20 118.8 . . ? C19 C20 H20 118.8 . . ? C17 N4 C16 107.9(3) . . ? C17 N4 H4 126.1 . . ? C16 N4 H4 126.1 . . ? 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 C11 C12 C13 C14 0.9(6) . . . . ? C12 C13 C14 C9 -0.7(5) . . . . ? C10 N1 C9 C8 0.7(4) . . . . ? C10 N1 C9 C14 -179.8(3) . . . . ? C13 C14 C9 C8 -0.1(5) . . . . ? C13 C14 C9 N1 -179.6(3) . . . . ? C8 N2 C10 N1 0.0(4) . . . . ? C9 N1 C10 N2 -0.4(4) . . . . ? C13 C12 C11 C8 -0.3(6) . . . . ? C12 C11 C8 N2 -179.2(3) . . . . ? C12 C11 C8 C9 -0.5(5) . . . . ? C10 N2 C8 C11 179.2(4) . . . . ? C10 N2 C8 C9 0.4(4) . . . . ? N1 C9 C8 C11 -179.6(3) . . . . ? C14 C9 C8 C11 0.8(5) . . . . ? N1 C9 C8 N2 -0.7(3) . . . . ? C14 C9 C8 N2 179.7(3) . . . . ? O4 C4 C5 C6 179.2(3) . . . . ? C3 C4 C5 C6 -3.6(5) . . . . ? O4 C4 C5 C7 -2.2(5) . . . . ? C3 C4 C5 C7 175.0(3) . . . . ? C4 C5 C6 C1 3.6(5) . . . . ? C7 C5 C6 C1 -175.1(3) . . . . ? C5 C6 C1 C2 -1.4(5) . . . . ? C5 C6 C1 S1 178.8(3) . . . . ? O1 S1 C1 C6 -154.4(3) . . . . ? O2 S1 C1 C6 85.1(3) . . . . ? O3 S1 C1 C6 -34.3(3) . . . . ? O1 S1 C1 C2 25.7(3) . . . . ? O2 S1 C1 C2 -94.8(3) . . . . ? O3 S1 C1 C2 145.8(3) . . . . ? C4 C5 C7 O5 -174.3(3) . . . . ? C6 C5 C7 O5 4.2(5) . . . . ? C4 C5 C7 O6 3.7(5) . . . . ? C6 C5 C7 O6 -177.7(3) . . . . ? O4 C4 C3 C2 178.9(3) . . . . ? C5 C4 C3 C2 1.6(5) . . . . ? C4 C3 C2 C1 0.7(6) . . . . ? C6 C1 C2 C3 -0.8(5) . . . . ? S1 C1 C2 C3 179.1(3) . . . . ? C15 N3 C17 N4 -0.4(4) . . . . ? C17 N3 C15 C18 -179.9(4) . . . . ? C17 N3 C15 C16 0.0(4) . . . . ? C16 C15 C18 C19 0.7(6) . . . . ? N3 C15 C18 C19 -179.5(4) . . . . ? C15 C18 C19 C20 -2.1(8) . . . . ? C18 C15 C16 N4 -179.8(4) . . . . ? N3 C15 C16 N4 0.4(4) . . . . ? C18 C15 C16 C21 0.4(6) . . . . ? N3 C15 C16 C21 -179.5(3) . . . . ? N4 C16 C21 C20 -179.9(4) . . . . ? C15 C16 C21 C20 -0.1(6) . . . . ? C16 C21 C20 C19 -1.4(7) . . . . ? C18 C19 C20 C21 2.6(8) . . . . ? N3 C17 N4 C16 0.6(4) . . . . ? C15 C16 N4 C17 -0.6(4) . . . . ? C21 C16 N4 C17 179.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 66.61 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.239 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 921357' ####################################################################### # # 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_1 #TrackingRef '1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 N2 O6 S' _chemical_formula_weight 336.33 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8714(5) _cell_length_b 16.5514(11) _cell_length_c 13.6543(7) _cell_angle_alpha 90.00 _cell_angle_beta 124.464(3) _cell_angle_gamma 90.00 _cell_volume 1466.69(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8985 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3345 _reflns_number_gt 3020 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0506P)^2^+0.9032P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3345 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 -0.64553(6) -0.46509(2) 0.20002(4) 0.03078(13) Uani 1 1 d . . . O1 O -0.7016(3) -0.42194(7) 0.09353(12) 0.0486(4) Uani 1 1 d . . . O2 O -0.4292(2) -0.49004(8) 0.26692(14) 0.0512(4) Uani 1 1 d . . . O3 O -0.7830(2) -0.53160(7) 0.17673(12) 0.0410(3) Uani 1 1 d . . . O4 O -0.6790(2) -0.11797(7) 0.38221(12) 0.0412(3) Uani 1 1 d . . . O5 O -0.6119(2) -0.15277(7) 0.24987(12) 0.0438(3) Uani 1 1 d . . . H2 H -0.5959 -0.1004 0.2478 0.066 Uiso 1 1 d R . . O6 O -0.7435(2) -0.23319(7) 0.49162(12) 0.0424(3) Uani 1 1 d . . . H3 H -0.7195 -0.1809 0.4793 0.064 Uiso 1 1 d R . . C5 C -0.6560(2) -0.31390(9) 0.27326(13) 0.0265(3) Uani 1 1 d . . . H5A H -0.6336 -0.2967 0.2166 0.032 Uiso 1 1 calc R . . C8 C -0.6692(2) -0.39540(9) 0.28930(14) 0.0273(3) Uani 1 1 d . . . C9 C -0.6762(2) -0.25700(9) 0.34164(13) 0.0259(3) Uani 1 1 d . . . C11 C -0.6575(2) -0.16992(9) 0.32671(14) 0.0294(3) Uani 1 1 d . . . C12 C -0.7034(3) -0.42160(10) 0.37388(15) 0.0356(4) Uani 1 1 d . . . H12A H -0.7108 -0.4766 0.3850 0.043 Uiso 1 1 calc R . . C14 C -0.7152(3) -0.28337(9) 0.42457(14) 0.0303(3) Uani 1 1 d . . . C19 C -0.7262(3) -0.36624(10) 0.44078(16) 0.0385(4) Uani 1 1 d . . . H19A H -0.7490 -0.3839 0.4970 0.046 Uiso 1 1 calc R . . N1 N -0.1628(2) -0.39588(9) 0.03166(13) 0.0359(3) Uani 1 1 d . . . H1A H -0.1308 -0.4096 -0.0167 0.043 Uiso 1 1 d R . . N2 N -0.2535(2) -0.40519(10) 0.15318(14) 0.0413(4) Uani 1 1 d . . . H2A H -0.2893 -0.4259 0.1967 0.050 Uiso 1 1 d R . . C15 C -0.1656(2) -0.31759(10) 0.06630(15) 0.0320(3) Uani 1 1 d . . . C16 C -0.2167(3) -0.44584(11) 0.08423(17) 0.0404(4) Uani 1 1 d . . . H16A H -0.2272 -0.5016 0.0742 0.049 Uiso 1 1 calc R . . C17 C -0.1231(3) -0.24388(12) 0.03660(19) 0.0458(4) Uani 1 1 d . . . H17A H -0.0821 -0.2401 -0.0151 0.055 Uiso 1 1 calc R . . C18 C -0.2250(3) -0.32356(11) 0.14417(15) 0.0362(4) Uani 1 1 d . . . C20 C -0.2450(3) -0.25488(15) 0.1957(2) 0.0547(6) Uani 1 1 d . . . H20A H -0.2845 -0.2583 0.2482 0.066 Uiso 1 1 calc R . . C21 C -0.1449(4) -0.17674(12) 0.0877(2) 0.0607(6) Uani 1 1 d . . . H21A H -0.1193 -0.1260 0.0694 0.073 Uiso 1 1 calc R . . C22 C -0.2040(4) -0.18244(14) 0.1659(2) 0.0632(7) Uani 1 1 d . . . H22A H -0.2160 -0.1354 0.1988 0.076 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 0.0453(2) 0.01828(19) 0.0408(2) -0.00363(14) 0.0317(2) -0.00044(14) O1 0.0911(11) 0.0279(6) 0.0531(8) -0.0008(5) 0.0566(8) -0.0009(6) O2 0.0497(8) 0.0396(7) 0.0674(9) -0.0097(7) 0.0350(7) 0.0085(6) O3 0.0631(8) 0.0259(6) 0.0502(7) -0.0099(5) 0.0418(7) -0.0119(5) O4 0.0634(8) 0.0227(6) 0.0507(7) -0.0079(5) 0.0402(7) -0.0023(5) O5 0.0742(9) 0.0234(6) 0.0564(8) -0.0067(5) 0.0505(8) -0.0120(6) O6 0.0686(9) 0.0309(6) 0.0505(7) -0.0096(5) 0.0472(7) -0.0049(6) C5 0.0328(7) 0.0216(7) 0.0313(7) -0.0018(6) 0.0218(6) -0.0017(6) C8 0.0350(8) 0.0199(6) 0.0322(7) -0.0029(6) 0.0221(7) 0.0003(6) C9 0.0301(7) 0.0204(7) 0.0304(7) -0.0033(5) 0.0190(6) -0.0022(5) C11 0.0340(8) 0.0222(7) 0.0341(8) -0.0041(6) 0.0206(7) -0.0036(6) C12 0.0549(10) 0.0212(7) 0.0411(9) 0.0004(6) 0.0334(8) -0.0021(7) C14 0.0386(8) 0.0262(7) 0.0329(8) -0.0057(6) 0.0242(7) -0.0027(6) C19 0.0614(11) 0.0295(8) 0.0406(9) -0.0012(7) 0.0385(9) -0.0045(7) N1 0.0426(8) 0.0317(7) 0.0419(8) -0.0088(6) 0.0290(7) -0.0015(6) N2 0.0423(8) 0.0477(9) 0.0417(8) -0.0033(7) 0.0285(7) -0.0084(7) C15 0.0296(7) 0.0299(8) 0.0358(8) -0.0064(6) 0.0180(7) -0.0007(6) C16 0.0430(10) 0.0313(8) 0.0462(10) -0.0057(7) 0.0248(8) -0.0058(7) C17 0.0440(10) 0.0391(10) 0.0522(11) 0.0025(8) 0.0259(9) -0.0028(8) C18 0.0311(8) 0.0414(9) 0.0371(8) -0.0095(7) 0.0198(7) -0.0022(7) C20 0.0448(11) 0.0663(14) 0.0533(12) -0.0247(10) 0.0279(10) 0.0027(10) C21 0.0514(12) 0.0303(10) 0.0767(16) -0.0039(10) 0.0220(11) -0.0009(8) C22 0.0547(13) 0.0440(12) 0.0727(15) -0.0251(11) 0.0251(12) 0.0055(10) _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 O1 1.4467(13) . ? S1 O3 1.4474(12) . ? S1 O2 1.4640(14) . ? S1 C8 1.7630(15) . ? O4 C11 1.2196(19) . ? O5 C11 1.3179(19) . ? O5 H2 0.8790 . ? O6 C14 1.3450(18) . ? O6 H3 0.9214 . ? C5 C8 1.380(2) . ? C5 C9 1.3970(19) . ? C5 H5A 0.9300 . ? C8 C12 1.395(2) . ? C9 C14 1.400(2) . ? C9 C11 1.475(2) . ? C12 C19 1.375(2) . ? C12 H12A 0.9300 . ? C14 C19 1.400(2) . ? C19 H19A 0.9300 . ? N1 C16 1.313(2) . ? N1 C15 1.384(2) . ? N1 H1A 0.8600 . ? N2 C16 1.316(2) . ? N2 C18 1.386(2) . ? N2 H2A 0.8600 . ? C15 C17 1.385(2) . ? C15 C18 1.386(2) . ? C16 H16A 0.9300 . ? C17 C21 1.373(3) . ? C17 H17A 0.9300 . ? C18 C20 1.392(3) . ? C20 C22 1.363(4) . ? C20 H20A 0.9300 . ? C21 C22 1.388(4) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? 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 O1 S1 O3 112.95(8) . . ? O1 S1 O2 110.60(9) . . ? O3 S1 O2 112.55(8) . . ? O1 S1 C8 106.30(7) . . ? O3 S1 C8 106.92(7) . . ? O2 S1 C8 107.08(8) . . ? C11 O5 H2 110.3 . . ? C14 O6 H3 109.0 . . ? C8 C5 C9 120.38(14) . . ? C8 C5 H5A 119.8 . . ? C9 C5 H5A 119.8 . . ? C5 C8 C12 120.15(14) . . ? C5 C8 S1 118.88(11) . . ? C12 C8 S1 120.96(12) . . ? C5 C9 C14 119.36(13) . . ? C5 C9 C11 120.56(13) . . ? C14 C9 C11 120.08(13) . . ? O4 C11 O5 122.61(14) . . ? O4 C11 C9 122.92(15) . . ? O5 C11 C9 114.46(13) . . ? C19 C12 C8 120.10(15) . . ? C19 C12 H12A 119.9 . . ? C8 C12 H12A 119.9 . . ? O6 C14 C19 116.66(14) . . ? O6 C14 C9 123.69(14) . . ? C19 C14 C9 119.65(14) . . ? C12 C19 C14 120.32(15) . . ? C12 C19 H19A 119.8 . . ? C14 C19 H19A 119.8 . . ? C16 N1 C15 109.30(14) . . ? C16 N1 H1A 125.3 . . ? C15 N1 H1A 125.3 . . ? C16 N2 C18 108.82(15) . . ? C16 N2 H2A 125.6 . . ? C18 N2 H2A 125.6 . . ? C17 C15 N1 132.19(17) . . ? C17 C15 C18 121.98(16) . . ? N1 C15 C18 105.83(15) . . ? N2 C16 N1 109.82(16) . . ? N2 C16 H16A 125.1 . . ? N1 C16 H16A 125.1 . . ? C21 C17 C15 116.4(2) . . ? C21 C17 H17A 121.8 . . ? C15 C17 H17A 121.8 . . ? N2 C18 C15 106.22(14) . . ? N2 C18 C20 132.91(18) . . ? C15 C18 C20 120.88(19) . . ? C22 C20 C18 117.0(2) . . ? C22 C20 H20A 121.5 . . ? C18 C20 H20A 121.5 . . ? C17 C21 C22 121.9(2) . . ? C17 C21 H21A 119.1 . . ? C22 C21 H21A 119.1 . . ? C20 C22 C21 121.93(19) . . ? C20 C22 H22A 119.0 . . ? C21 C22 H22A 119.0 . . ? 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 C9 C5 C8 C12 0.2(2) . . . . ? C9 C5 C8 S1 179.35(12) . . . . ? O1 S1 C8 C5 -23.62(16) . . . . ? O3 S1 C8 C5 -144.52(13) . . . . ? O2 S1 C8 C5 94.63(14) . . . . ? O1 S1 C8 C12 155.54(15) . . . . ? O3 S1 C8 C12 34.64(16) . . . . ? O2 S1 C8 C12 -86.20(15) . . . . ? C8 C5 C9 C14 -1.6(2) . . . . ? C8 C5 C9 C11 178.60(14) . . . . ? C5 C9 C11 O4 178.13(16) . . . . ? C14 C9 C11 O4 -1.6(2) . . . . ? C5 C9 C11 O5 -3.0(2) . . . . ? C14 C9 C11 O5 177.19(15) . . . . ? C5 C8 C12 C19 0.7(3) . . . . ? S1 C8 C12 C19 -178.49(14) . . . . ? C5 C9 C14 O6 -177.79(15) . . . . ? C11 C9 C14 O6 2.0(2) . . . . ? C5 C9 C14 C19 2.2(2) . . . . ? C11 C9 C14 C19 -177.99(16) . . . . ? C8 C12 C19 C14 0.0(3) . . . . ? O6 C14 C19 C12 178.60(17) . . . . ? C9 C14 C19 C12 -1.4(3) . . . . ? C16 N1 C15 C17 -179.64(19) . . . . ? C16 N1 C15 C18 0.08(19) . . . . ? C18 N2 C16 N1 0.9(2) . . . . ? C15 N1 C16 N2 -0.6(2) . . . . ? N1 C15 C17 C21 179.09(19) . . . . ? C18 C15 C17 C21 -0.6(3) . . . . ? C16 N2 C18 C15 -0.8(2) . . . . ? C16 N2 C18 C20 179.2(2) . . . . ? C17 C15 C18 N2 -179.81(16) . . . . ? N1 C15 C18 N2 0.44(18) . . . . ? C17 C15 C18 C20 0.2(3) . . . . ? N1 C15 C18 C20 -179.57(16) . . . . ? N2 C18 C20 C22 -179.9(2) . . . . ? C15 C18 C20 C22 0.1(3) . . . . ? C15 C17 C21 C22 0.7(3) . . . . ? C18 C20 C22 C21 0.0(3) . . . . ? C17 C21 C22 C20 -0.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.717 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.105 _database_code_depnum_ccdc_archive 'CCDC 924303'