# Supplementary Material (ESI) for Green Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global #TrackingRef 'C0GC00442A_ccdc_776454_776455_cif.txt' _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _publ_contact_author_email a-shaabani@cc.sbu.ac.ir _publ_contact_author_name 'Shaabani, Ahmad' _publ_section_title ; An environmentally benign approach for the synthesis of bifunctional sulfonamide-amide compounds via isocyanide-based multicomponent reactions ; loop_ _publ_author_name A.Shaabani A.Sarvary S.Ghasemi A.H.Rezayan R.Ghadari data_4a _database_code_depnum_ccdc_archive 'CCDC 776454' #TrackingRef '4a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H36 N2 O6 S' _chemical_formula_weight 480.61 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.818(2) _cell_length_b 10.459(2) _cell_length_c 16.684(4) _cell_angle_alpha 73.495(3) _cell_angle_beta 82.566(4) _cell_angle_gamma 65.165(3) _cell_volume 1338.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9689 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 10652 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_sigmaI/netI 0.1062 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4721 _reflns_number_gt 2169 _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^)+(0.1287P)^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 4721 _refine_ls_number_parameters 299 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.1706 _refine_ls_R_factor_gt 0.0722 _refine_ls_wR_factor_ref 0.2562 _refine_ls_wR_factor_gt 0.1940 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.002 _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 0.19178(17) 0.76495(15) 0.33048(9) 0.0557(5) Uani 1 1 d . . . N1 N 0.2324(4) 0.6199(4) 0.4061(2) 0.0441(10) Uani 1 1 d . . . H1 H 0.2426 0.6236 0.4559 0.053 Uiso 1 1 calc R . . N2 N 0.4369(6) 0.3781(5) 0.2035(3) 0.0623(13) Uani 1 1 d . . . O1 O 0.1465(5) 0.8829(4) 0.3677(3) 0.0758(12) Uani 1 1 d . . . O2 O 0.0774(4) 0.7647(4) 0.2768(2) 0.0713(11) Uani 1 1 d . . . O3 O 0.2597(4) 0.2552(4) 0.4690(2) 0.0579(10) Uani 1 1 d . . . O4 O 0.1838(5) 0.4252(4) 0.5398(2) 0.0640(11) Uani 1 1 d . . . O5 O 0.7065(4) 0.3239(4) 0.3475(2) 0.0560(10) Uani 1 1 d . . . O6 O 0.5682(4) 0.3695(4) 0.4661(2) 0.0561(10) Uani 1 1 d . . . C1 C 0.3785(7) 0.7508(5) 0.2729(3) 0.0509(13) Uani 1 1 d . . . C2 C 0.5209(7) 0.7234(6) 0.3123(3) 0.0583(14) Uani 1 1 d . . . H2 H 0.5189 0.7116 0.3697 0.070 Uiso 1 1 calc R . . C3 C 0.6646(7) 0.7133(6) 0.2680(4) 0.0666(16) Uani 1 1 d . . . H3 H 0.7594 0.6952 0.2956 0.080 Uiso 1 1 calc R . . C4 C 0.6716(8) 0.7296(7) 0.1828(4) 0.0716(17) Uani 1 1 d . . . C5 C 0.5279(9) 0.7576(8) 0.1444(4) 0.089(2) Uani 1 1 d . . . H5 H 0.5296 0.7705 0.0869 0.107 Uiso 1 1 calc R . . C6 C 0.3818(8) 0.7674(7) 0.1882(3) 0.0750(18) Uani 1 1 d . . . H6 H 0.2868 0.7850 0.1609 0.090 Uiso 1 1 calc R . . C7 C 0.8323(9) 0.7181(9) 0.1337(4) 0.108(3) Uani 1 1 d . . . H7A H 0.8891 0.7605 0.1564 0.162 Uiso 1 1 calc R . . H7B H 0.8065 0.7690 0.0762 0.162 Uiso 1 1 calc R . . H7C H 0.9028 0.6174 0.1376 0.162 Uiso 1 1 calc R . . C8 C 0.2521(6) 0.4822(5) 0.3919(3) 0.0425(12) Uani 1 1 d . . . H8 H 0.1615 0.5024 0.3556 0.051 Uiso 1 1 calc R . . C9 C 0.2295(6) 0.3860(6) 0.4768(3) 0.0478(12) Uani 1 1 d . . . C10 C 0.2349(9) 0.1550(7) 0.5451(4) 0.085(2) Uani 1 1 d . . . H10A H 0.3103 0.1388 0.5879 0.102 Uiso 1 1 calc R . . H10B H 0.1212 0.1967 0.5655 0.102 Uiso 1 1 calc R . . C11 C 0.2669(9) 0.0174(7) 0.5274(5) 0.110(3) Uani 1 1 d . . . H11A H 0.2511 -0.0488 0.5776 0.164 Uiso 1 1 calc R . . H11B H 0.3797 -0.0236 0.5075 0.164 Uiso 1 1 calc R . . H11C H 0.1909 0.0339 0.4856 0.164 Uiso 1 1 calc R . . C12 C 0.4161(6) 0.4090(5) 0.3498(3) 0.0428(12) Uani 1 1 d . . . C13 C 0.5699(6) 0.3659(5) 0.3943(3) 0.0462(12) Uani 1 1 d . . . C14 C 0.8639(6) 0.2888(7) 0.3855(4) 0.0713(17) Uani 1 1 d . . . H14A H 0.8519 0.3643 0.4117 0.086 Uiso 1 1 calc R . . H14B H 0.8948 0.1972 0.4280 0.086 Uiso 1 1 calc R . . C15 C 0.9903(8) 0.2780(9) 0.3218(4) 0.098(2) Uani 1 1 d . . . H15A H 1.0954 0.2514 0.3464 0.147 Uiso 1 1 calc R . . H15B H 0.9613 0.3703 0.2812 0.147 Uiso 1 1 calc R . . H15C H 0.9992 0.2051 0.2950 0.147 Uiso 1 1 calc R . . C16 C 0.4247(6) 0.3879(5) 0.2738(3) 0.0499(13) Uani 1 1 d . . . C17 C 0.4515(9) 0.2560(8) 0.1713(4) 0.083(2) Uani 1 1 d . . . C18 C 0.4671(11) 0.1251(8) 0.2419(5) 0.112(3) Uani 1 1 d . . . H18A H 0.5756 0.0837 0.2664 0.168 Uiso 1 1 calc R . . H18B H 0.4532 0.0541 0.2211 0.168 Uiso 1 1 calc R . . H18C H 0.3826 0.1536 0.2835 0.168 Uiso 1 1 calc R . . C19 C 0.2766(12) 0.3095(11) 0.1295(5) 0.145(4) Uani 1 1 d . . . H19A H 0.2631 0.3909 0.0821 0.218 Uiso 1 1 calc R . . H19B H 0.1885 0.3384 0.1694 0.218 Uiso 1 1 calc R . . H19C H 0.2723 0.2315 0.1117 0.218 Uiso 1 1 calc R . . C20 C 0.5759(9) 0.2469(10) 0.0985(5) 0.130(3) Uani 1 1 d D . . H20A H 0.5219 0.3337 0.0544 0.156 Uiso 1 1 calc R . . H20B H 0.5832 0.1655 0.0790 0.156 Uiso 1 1 calc R . . C21 C 0.7551(7) 0.2313(7) 0.1004(4) 0.0734(17) Uani 1 1 d D . . C22 C 0.8187(12) 0.2081(12) 0.0162(5) 0.168(4) Uani 1 1 d DU . . H22A H 0.9328 0.1974 0.0097 0.252 Uiso 1 1 calc R . . H22B H 0.7520 0.2904 -0.0261 0.252 Uiso 1 1 calc R . . H22C H 0.8121 0.1216 0.0109 0.252 Uiso 1 1 calc R . . C23 C 0.8494(14) 0.1128(10) 0.1681(6) 0.209(6) Uani 1 1 d DU . . H23A H 0.9592 0.1106 0.1686 0.313 Uiso 1 1 calc R . . H23B H 0.8581 0.0223 0.1606 0.313 Uiso 1 1 calc R . . H23C H 0.7935 0.1268 0.2203 0.313 Uiso 1 1 calc R . . C24 C 0.7537(8) 0.3703(7) 0.1085(4) 0.095(2) Uani 1 1 d DU . . H24A H 0.8664 0.3597 0.1118 0.143 Uiso 1 1 calc R . . H24B H 0.6930 0.3930 0.1582 0.143 Uiso 1 1 calc R . . H24C H 0.7007 0.4475 0.0606 0.143 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 0.0563(9) 0.0467(9) 0.0553(9) -0.0082(7) -0.0028(7) -0.0150(7) N1 0.052(2) 0.039(2) 0.039(2) -0.0125(18) 0.0023(18) -0.0146(19) N2 0.072(3) 0.076(3) 0.045(3) -0.028(2) 0.006(2) -0.029(3) O1 0.082(3) 0.041(2) 0.094(3) -0.024(2) 0.014(2) -0.0146(19) O2 0.060(2) 0.076(3) 0.066(2) 0.006(2) -0.024(2) -0.025(2) O3 0.065(2) 0.043(2) 0.066(2) -0.0130(18) 0.0091(18) -0.0261(18) O4 0.080(3) 0.072(3) 0.047(2) -0.0218(19) 0.0157(19) -0.037(2) O5 0.044(2) 0.072(3) 0.050(2) -0.0248(18) 0.0067(17) -0.0187(18) O6 0.057(2) 0.068(2) 0.045(2) -0.0227(18) -0.0032(17) -0.0216(18) C1 0.065(4) 0.046(3) 0.045(3) -0.006(2) 0.000(3) -0.030(3) C2 0.068(4) 0.068(4) 0.046(3) -0.011(3) 0.000(3) -0.037(3) C3 0.067(4) 0.075(4) 0.068(4) -0.020(3) 0.000(3) -0.037(3) C4 0.086(5) 0.078(4) 0.068(4) -0.030(3) 0.021(4) -0.047(4) C5 0.113(6) 0.128(6) 0.046(4) -0.028(4) 0.017(4) -0.069(5) C6 0.081(4) 0.108(5) 0.043(3) -0.012(3) -0.004(3) -0.050(4) C7 0.112(6) 0.139(7) 0.100(5) -0.051(5) 0.044(5) -0.076(5) C8 0.048(3) 0.045(3) 0.036(3) -0.014(2) -0.002(2) -0.018(2) C9 0.039(3) 0.049(3) 0.056(3) -0.016(3) -0.001(2) -0.017(2) C10 0.103(5) 0.060(4) 0.091(5) -0.009(4) 0.018(4) -0.045(4) C11 0.117(6) 0.070(5) 0.143(7) -0.021(5) 0.010(5) -0.045(4) C12 0.045(3) 0.043(3) 0.045(3) -0.016(2) 0.002(2) -0.019(2) C13 0.049(3) 0.044(3) 0.047(3) -0.015(2) 0.004(2) -0.019(2) C14 0.050(4) 0.088(5) 0.076(4) -0.021(3) -0.004(3) -0.026(3) C15 0.060(4) 0.156(7) 0.089(5) -0.049(5) 0.014(4) -0.046(4) C16 0.049(3) 0.050(3) 0.049(3) -0.016(3) 0.004(2) -0.017(2) C17 0.112(6) 0.097(5) 0.068(4) -0.046(4) 0.029(4) -0.060(4) C18 0.164(8) 0.082(5) 0.101(6) -0.039(5) 0.021(5) -0.055(5) C19 0.179(10) 0.201(11) 0.112(7) -0.054(7) -0.020(6) -0.116(8) C20 0.149(8) 0.158(8) 0.125(7) -0.091(6) 0.062(6) -0.084(7) C21 0.061(4) 0.089(5) 0.070(4) -0.030(4) 0.000(3) -0.023(3) C22 0.188(9) 0.225(11) 0.122(7) -0.105(7) 0.059(7) -0.090(8) C23 0.270(13) 0.121(8) 0.211(11) -0.019(8) -0.104(10) -0.041(8) C24 0.094(5) 0.099(5) 0.104(5) -0.035(4) 0.015(4) -0.049(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.423(4) . ? S1 O2 1.434(4) . ? S1 N1 1.611(4) . ? S1 C1 1.768(5) . ? N1 C8 1.460(6) . ? N2 C16 1.194(6) . ? N2 C17 1.473(7) . ? O3 C9 1.322(6) . ? O3 C10 1.457(6) . ? O4 C9 1.196(5) . ? O5 C13 1.326(5) . ? O5 C14 1.459(6) . ? O6 C13 1.208(5) . ? C1 C6 1.371(7) . ? C1 C2 1.376(7) . ? C2 C3 1.361(7) . ? C3 C4 1.379(8) . ? C4 C5 1.376(8) . ? C4 C7 1.518(8) . ? C5 C6 1.376(8) . ? C8 C12 1.511(6) . ? C8 C9 1.530(7) . ? C10 C11 1.455(8) . ? C12 C16 1.335(7) . ? C12 C13 1.466(7) . ? C14 C15 1.428(8) . ? C17 C18 1.500(9) . ? C17 C20 1.524(9) . ? C17 C19 1.584(10) . ? C20 C21 1.522(7) . ? C21 C23 1.444(7) . ? C21 C22 1.490(7) . ? C21 C24 1.492(7) . ? 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 120.2(3) . . ? O1 S1 N1 106.6(2) . . ? O2 S1 N1 106.7(2) . . ? O1 S1 C1 107.1(2) . . ? O2 S1 C1 107.6(2) . . ? N1 S1 C1 108.1(2) . . ? C8 N1 S1 121.4(3) . . ? C16 N2 C17 129.8(5) . . ? C9 O3 C10 114.9(4) . . ? C13 O5 C14 116.4(4) . . ? C6 C1 C2 119.7(5) . . ? C6 C1 S1 119.8(4) . . ? C2 C1 S1 120.5(4) . . ? C3 C2 C1 120.6(5) . . ? C2 C3 C4 121.1(6) . . ? C5 C4 C3 117.5(6) . . ? C5 C4 C7 121.7(6) . . ? C3 C4 C7 120.8(6) . . ? C4 C5 C6 122.3(6) . . ? C1 C6 C5 118.9(6) . . ? N1 C8 C12 113.2(4) . . ? N1 C8 C9 106.9(4) . . ? C12 C8 C9 112.5(4) . . ? O4 C9 O3 125.1(5) . . ? O4 C9 C8 125.3(5) . . ? O3 C9 C8 109.6(4) . . ? C11 C10 O3 109.4(6) . . ? C16 C12 C13 120.0(4) . . ? C16 C12 C8 122.6(4) . . ? C13 C12 C8 117.4(4) . . ? O6 C13 O5 124.9(5) . . ? O6 C13 C12 122.0(4) . . ? O5 C13 C12 113.1(4) . . ? C15 C14 O5 108.8(5) . . ? N2 C16 C12 174.6(5) . . ? N2 C17 C18 110.6(5) . . ? N2 C17 C20 107.7(5) . . ? C18 C17 C20 121.7(6) . . ? N2 C17 C19 104.4(6) . . ? C18 C17 C19 106.4(6) . . ? C20 C17 C19 104.6(6) . . ? C17 C20 C21 126.6(6) . . ? C23 C21 C22 113.3(6) . . ? C23 C21 C24 109.3(6) . . ? C22 C21 C24 110.6(6) . . ? C23 C21 C20 112.6(7) . . ? C22 C21 C20 101.7(5) . . ? C24 C21 C20 109.2(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O6 0.86 2.28 2.986(5) 139.4 2_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.796 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.105 # Attachment 'B.CIF' data_b _database_code_depnum_ccdc_archive 'CCDC 776455' #TrackingRef 'B.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 N2 O7 S' _chemical_formula_weight 490.56 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 21/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 11.2071(8) _cell_length_b 23.3231(15) _cell_length_c 11.1208(8) _cell_angle_alpha 90.00 _cell_angle_beta 117.989(1) _cell_angle_gamma 90.00 _cell_volume 2566.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5768 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25.2 _exptl_crystal_description Irregular _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9428 _exptl_absorpt_correction_T_max 0.9586 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24249 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5904 _reflns_number_gt 4121 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 software (Bruker, 2008)' _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'publCIF (Westrip, 2009)' _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^)+(0.0547P)^2^+2.6886P] 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 5904 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0912 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1768 _refine_ls_wR_factor_gt 0.1576 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.001 _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 0.23322(7) 0.58029(3) 0.51711(7) 0.0451(2) Uani 1 1 d . . . O1 O 0.0928(2) 0.57305(10) 0.4793(3) 0.0631(6) Uani 1 1 d . . . O2 O 0.3257(3) 0.59846(10) 0.6517(2) 0.0632(6) Uani 1 1 d . . . O3 O 0.2222(2) 0.42561(10) 0.2158(2) 0.0573(6) Uani 1 1 d . . . O4 O 0.4080(2) 0.47492(10) 0.3540(2) 0.0558(6) Uani 1 1 d . . . O5 O -0.0549(2) 0.43502(11) 0.1918(2) 0.0679(7) Uani 1 1 d . . . O6 O 0.0238(3) 0.35082(11) 0.2937(3) 0.0775(8) Uani 1 1 d . . . O7 O 0.3336(2) 0.38593(11) 0.5243(2) 0.0651(7) Uani 1 1 d . . . N1 N 0.2865(2) 0.51882(9) 0.4955(2) 0.0392(5) Uani 1 1 d . . . H1 H 0.3639 0.5062 0.5554 0.047 Uiso 1 1 calc R . . N2 N 0.1964(2) 0.38594(10) 0.6206(2) 0.0448(5) Uani 1 1 d . . . H2 H 0.1193 0.3968 0.6115 0.054 Uiso 1 1 calc R . . C1 C 0.2419(3) 0.62818(11) 0.3993(3) 0.0413(6) Uani 1 1 d . . . C2 C 0.1309(3) 0.66075(14) 0.3150(3) 0.0589(8) Uani 1 1 d . . . H2A H 0.0491 0.6559 0.3162 0.071 Uiso 1 1 calc R . . C3 C 0.1424(4) 0.70048(16) 0.2291(4) 0.0695(10) Uani 1 1 d . . . H3 H 0.0681 0.7229 0.1737 0.083 Uiso 1 1 calc R . . C4 C 0.2629(4) 0.70760(14) 0.2239(3) 0.0595(8) Uani 1 1 d . . . C5 C 0.3713(3) 0.67404(14) 0.3072(3) 0.0578(8) Uani 1 1 d . . . H5 H 0.4522 0.6778 0.3036 0.069 Uiso 1 1 calc R . . C6 C 0.3627(3) 0.63499(13) 0.3959(3) 0.0511(7) Uani 1 1 d . . . H6 H 0.4378 0.6134 0.4531 0.061 Uiso 1 1 calc R . . C7 C 0.2736(5) 0.75102(19) 0.1294(5) 0.0980(15) Uani 1 1 d . . . H7A H 0.3671 0.7584 0.1566 0.147 Uiso 1 1 calc R . . H7B H 0.2303 0.7860 0.1331 0.147 Uiso 1 1 calc R . . H7C H 0.2302 0.7364 0.0380 0.147 Uiso 1 1 calc R . . C8 C 0.2040(3) 0.48453(11) 0.3749(3) 0.0377(6) Uani 1 1 d . . . H8 H 0.1368 0.5099 0.3063 0.045 Uiso 1 1 calc R . . C9 C 0.1277(3) 0.43827(11) 0.4113(3) 0.0385(6) Uani 1 1 d . . . H9 H 0.0754 0.4582 0.4487 0.046 Uiso 1 1 calc R . . C10 C 0.2933(3) 0.46092(12) 0.3174(3) 0.0424(6) Uani 1 1 d . . . C11 C 0.2879(4) 0.39892(18) 0.1441(4) 0.0702(10) Uani 1 1 d . . . H11A H 0.3375 0.3651 0.1924 0.084 Uiso 1 1 calc R . . H11B H 0.3503 0.4255 0.1359 0.084 Uiso 1 1 calc R . . C12 C 0.1771(5) 0.3831(2) 0.0067(4) 0.0898(13) Uani 1 1 d . . . H12A H 0.2137 0.3613 -0.0415 0.135 Uiso 1 1 calc R . . H12B H 0.1355 0.4174 -0.0435 0.135 Uiso 1 1 calc R . . H12C H 0.1107 0.3605 0.0168 0.135 Uiso 1 1 calc R . . C13 C 0.0287(3) 0.40175(15) 0.2932(3) 0.0508(7) Uani 1 1 d . . . C14 C -0.1550(5) 0.4046(2) 0.0703(4) 0.1034(17) Uani 1 1 d . . . H14A H -0.1137 0.3715 0.0518 0.124 Uiso 1 1 calc R . . H14B H -0.2294 0.3914 0.0848 0.124 Uiso 1 1 calc R . . C15 C -0.2031(6) 0.4436(2) -0.0416(5) 0.131(2) Uani 1 1 d . . . H15A H -0.2673 0.4245 -0.1228 0.197 Uiso 1 1 calc R . . H15B H -0.1285 0.4569 -0.0541 0.197 Uiso 1 1 calc R . . H15C H -0.2457 0.4757 -0.0233 0.197 Uiso 1 1 calc R . . C16 C 0.2290(3) 0.40031(11) 0.5236(3) 0.0402(6) Uani 1 1 d . . . C17 C 0.2830(3) 0.35333(15) 0.7395(3) 0.0534(8) Uani 1 1 d . . . C18 C 0.2572(5) 0.29561(17) 0.7439(4) 0.0769(12) Uani 1 1 d . . . C19 C 0.3412(8) 0.2665(3) 0.8642(7) 0.123(2) Uani 1 1 d . . . H19 H 0.3278 0.2276 0.8717 0.148 Uiso 1 1 calc R . . C20 C 0.4422(7) 0.2945(4) 0.9704(7) 0.139(3) Uani 1 1 d . . . H20 H 0.4960 0.2743 1.0498 0.167 Uiso 1 1 calc R . . C21 C 0.4666(5) 0.3512(3) 0.9638(5) 0.115(2) Uani 1 1 d . . . H21 H 0.5372 0.3691 1.0376 0.138 Uiso 1 1 calc R . . C22 C 0.3861(4) 0.3823(2) 0.8467(4) 0.0777(12) Uani 1 1 d . . . C23 C 0.4083(6) 0.4452(3) 0.8391(5) 0.122(2) Uani 1 1 d . . . H23A H 0.3250 0.4654 0.8126 0.183 Uiso 1 1 calc R . . H23B H 0.4392 0.4520 0.7731 0.183 Uiso 1 1 calc R . . H23C H 0.4750 0.4587 0.9266 0.183 Uiso 1 1 calc R . . C24 C 0.1461(6) 0.26576(19) 0.6246(6) 0.1130(18) Uani 1 1 d . . . H24A H 0.0713 0.2915 0.5791 0.170 Uiso 1 1 calc R . . H24B H 0.1173 0.2328 0.6558 0.170 Uiso 1 1 calc R . . H24C H 0.1786 0.2539 0.5625 0.170 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 0.0480(4) 0.0445(4) 0.0474(4) -0.0002(3) 0.0262(3) 0.0060(3) O1 0.0529(13) 0.0653(14) 0.0853(16) 0.0102(12) 0.0443(13) 0.0120(11) O2 0.0826(17) 0.0590(14) 0.0457(12) -0.0085(10) 0.0281(12) 0.0055(12) O3 0.0548(13) 0.0708(15) 0.0533(12) -0.0194(11) 0.0311(11) -0.0124(11) O4 0.0406(11) 0.0759(15) 0.0533(12) -0.0080(11) 0.0240(10) -0.0067(10) O5 0.0468(13) 0.0748(16) 0.0542(13) 0.0059(11) 0.0006(11) -0.0097(11) O6 0.0793(18) 0.0537(15) 0.0760(17) -0.0051(13) 0.0168(14) -0.0146(13) O7 0.0524(13) 0.0860(17) 0.0669(14) 0.0307(13) 0.0362(12) 0.0286(12) N1 0.0345(11) 0.0399(12) 0.0388(12) 0.0016(10) 0.0135(10) 0.0042(9) N2 0.0386(12) 0.0529(14) 0.0447(13) 0.0092(11) 0.0208(10) 0.0070(10) C1 0.0407(15) 0.0367(14) 0.0430(14) -0.0015(11) 0.0167(12) 0.0039(11) C2 0.0434(17) 0.060(2) 0.064(2) 0.0083(16) 0.0171(15) 0.0098(14) C3 0.062(2) 0.063(2) 0.063(2) 0.0207(18) 0.0132(18) 0.0174(17) C4 0.066(2) 0.0443(17) 0.0556(19) 0.0074(14) 0.0181(16) -0.0011(15) C5 0.0549(19) 0.0510(18) 0.067(2) 0.0067(16) 0.0285(16) -0.0069(15) C6 0.0448(16) 0.0456(16) 0.0597(18) 0.0085(14) 0.0218(14) 0.0061(13) C7 0.115(4) 0.075(3) 0.091(3) 0.035(2) 0.038(3) -0.005(3) C8 0.0327(13) 0.0411(14) 0.0360(13) 0.0041(11) 0.0134(11) 0.0035(11) C9 0.0329(13) 0.0438(14) 0.0378(13) 0.0013(11) 0.0157(11) 0.0020(11) C10 0.0443(16) 0.0460(15) 0.0360(14) 0.0053(12) 0.0181(12) 0.0025(12) C11 0.077(2) 0.081(3) 0.067(2) -0.0183(19) 0.045(2) -0.003(2) C12 0.105(3) 0.105(3) 0.072(3) -0.033(2) 0.051(3) -0.017(3) C13 0.0394(16) 0.059(2) 0.0484(17) 0.0027(14) 0.0159(13) -0.0033(14) C14 0.072(3) 0.104(3) 0.075(3) -0.002(3) -0.015(2) -0.024(2) C15 0.144(5) 0.114(4) 0.063(3) -0.005(3) -0.012(3) -0.014(4) C16 0.0373(14) 0.0398(14) 0.0431(14) 0.0020(11) 0.0187(12) 0.0032(11) C17 0.0493(17) 0.068(2) 0.0485(17) 0.0160(15) 0.0272(15) 0.0170(15) C18 0.109(3) 0.061(2) 0.082(3) 0.020(2) 0.063(3) 0.030(2) C19 0.188(6) 0.095(4) 0.114(4) 0.057(4) 0.093(5) 0.072(4) C20 0.142(6) 0.186(7) 0.093(4) 0.080(5) 0.057(4) 0.094(5) C21 0.068(3) 0.199(7) 0.065(3) 0.042(4) 0.019(2) 0.025(4) C22 0.055(2) 0.117(4) 0.053(2) 0.017(2) 0.0190(18) 0.001(2) C23 0.113(4) 0.143(5) 0.077(3) -0.015(3) 0.016(3) -0.066(4) C24 0.184(6) 0.055(2) 0.124(4) -0.015(3) 0.093(4) -0.015(3) 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 O2 1.428(2) . ? S1 O1 1.435(2) . ? S1 N1 1.614(2) . ? S1 C1 1.759(3) . ? O3 C10 1.321(3) . ? O3 C11 1.455(4) . ? O4 C10 1.197(3) . ? O5 C13 1.327(4) . ? O5 C14 1.471(4) . ? O6 C13 1.189(4) . ? O7 C16 1.216(3) . ? N1 C8 1.460(3) . ? N2 C16 1.333(3) . ? N2 C17 1.437(4) . ? C1 C6 1.381(4) . ? C1 C2 1.381(4) . ? C2 C3 1.380(5) . ? C3 C4 1.388(5) . ? C4 C5 1.375(5) . ? C4 C7 1.505(5) . ? C5 C6 1.379(4) . ? C8 C10 1.521(4) . ? C8 C9 1.544(4) . ? C9 C16 1.517(4) . ? C9 C13 1.521(4) . ? C11 C12 1.494(5) . ? C14 C15 1.428(7) . ? C17 C18 1.382(5) . ? C17 C22 1.386(5) . ? C18 C19 1.399(6) . ? C18 C24 1.498(7) . ? C19 C20 1.359(9) . ? C20 C21 1.359(10) . ? C21 C22 1.391(6) . ? C22 C23 1.497(7) . ? 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 O2 S1 O1 119.89(15) . . ? O2 S1 N1 106.40(13) . . ? O1 S1 N1 106.47(13) . . ? O2 S1 C1 109.02(14) . . ? O1 S1 C1 107.04(14) . . ? N1 S1 C1 107.43(12) . . ? C10 O3 C11 118.5(2) . . ? C13 O5 C14 115.4(3) . . ? C8 N1 S1 120.29(17) . . ? C16 N2 C17 123.7(2) . . ? C6 C1 C2 120.0(3) . . ? C6 C1 S1 119.4(2) . . ? C2 C1 S1 120.5(2) . . ? C3 C2 C1 119.5(3) . . ? C2 C3 C4 121.2(3) . . ? C5 C4 C3 118.3(3) . . ? C5 C4 C7 121.2(4) . . ? C3 C4 C7 120.5(3) . . ? C4 C5 C6 121.4(3) . . ? C5 C6 C1 119.6(3) . . ? N1 C8 C10 109.1(2) . . ? N1 C8 C9 109.4(2) . . ? C10 C8 C9 114.3(2) . . ? C16 C9 C13 110.2(2) . . ? C16 C9 C8 109.3(2) . . ? C13 C9 C8 115.7(2) . . ? O4 C10 O3 125.6(3) . . ? O4 C10 C8 124.9(3) . . ? O3 C10 C8 109.4(2) . . ? O3 C11 C12 105.9(3) . . ? O6 C13 O5 124.9(3) . . ? O6 C13 C9 124.9(3) . . ? O5 C13 C9 110.1(3) . . ? C15 C14 O5 107.8(4) . . ? O7 C16 N2 123.7(3) . . ? O7 C16 C9 120.9(2) . . ? N2 C16 C9 115.4(2) . . ? C18 C17 C22 123.3(3) . . ? C18 C17 N2 119.1(3) . . ? C22 C17 N2 117.6(3) . . ? C17 C18 C19 116.7(5) . . ? C17 C18 C24 121.5(4) . . ? C19 C18 C24 121.9(5) . . ? C20 C19 C18 120.7(6) . . ? C21 C20 C19 121.8(5) . . ? C20 C21 C22 120.0(6) . . ? C17 C22 C21 117.6(5) . . ? C17 C22 C23 121.5(4) . . ? C21 C22 C23 120.9(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.86 2.31 3.027(3) 141.3 3_666 N2 H2 O1 0.86 2.22 3.046(3) 162.0 3_566 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.335 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.046