data_org_lett_3g _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H26 N2 O6 S' _chemical_formula_weight 506.56 _chemical_absolute_configuration ad 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.945(3) _cell_length_b 17.2536(5) _cell_length_c 20.6291(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2471.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16776 _cell_measurement_theta_min 3.3366 _cell_measurement_theta_max 61.1163 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 1.551 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8357 _exptl_absorpt_correction_T_max 0.8860 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; CheckCIF Alert THETM01_ALERT_3_B arises because of the restriction placed on the maximum two-theta achievable on the Gemini Enhance Ultra copper source when the Moly collimator is installed The crystal itself appears to have fractured at low temperature during the experiment and been held together by the frozen oil drop - on returning to room temperature, the crystal consisted of a series of much smaller crystals. As a result, the diffraction data quality is not particularly high-quality, as evidenced by the large R(int) and several level C alerts that are rleated to the structure. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator 'mirror' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _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 41878 _diffrn_reflns_av_R_equivalents 0.1525 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 60.83 _reflns_number_total 3681 _reflns_number_gt 3329 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^ > 2\s(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^)+(0.0444P)^2^+0.0289P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.022(17) _refine_ls_number_reflns 3681 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 -0.23222(9) -0.02561(3) 0.06860(3) 0.02498(16) Uani 1 1 d . . . O1 O -0.2743(3) -0.05346(9) 0.13252(7) 0.0328(4) Uani 1 1 d . . . O2 O -0.3607(2) 0.02790(9) 0.03694(8) 0.0293(4) Uani 1 1 d . . . O5 O -0.1288(3) 0.16404(11) 0.25383(9) 0.0490(5) Uani 1 1 d . . . O4 O 0.3925(3) 0.18041(11) -0.05773(10) 0.0486(5) Uani 1 1 d . . . N2 N 0.2496(4) 0.18329(10) -0.02475(9) 0.0298(5) Uani 1 1 d . . . C6 C 0.2296(4) 0.12672(11) 0.03112(11) 0.0240(5) Uani 1 1 d . . . H6 H 0.3444 0.0918 0.0316 0.029 Uiso 1 1 calc R . . C1 C 0.0481(4) 0.07779(12) 0.01720(11) 0.0223(5) Uani 1 1 d . . . H1 H -0.0613 0.1148 0.0112 0.027 Uiso 1 1 calc R . . O3 O 0.1205(3) 0.23005(11) -0.03320(10) 0.0520(5) Uani 1 1 d . . . C12 C 0.0753(3) 0.03523(12) -0.04712(11) 0.0245(5) Uani 1 1 d . . . C20 C 0.2650(4) -0.05373(13) -0.11322(13) 0.0370(6) Uani 1 1 d . . . H20 H 0.3699 -0.0889 -0.1164 0.044 Uiso 1 1 calc R . . C13 C -0.0466(4) 0.05026(12) -0.10202(11) 0.0259(6) Uani 1 1 d . . . O6 O -0.3266(4) 0.23702(13) 0.19458(10) 0.0727(8) Uani 1 1 d . . . N1 N 0.2528(4) -0.08041(11) 0.10583(11) 0.0407(5) Uani 1 1 d . . . C22 C -0.2009(3) -0.10619(12) 0.01755(11) 0.0252(6) Uani 1 1 d . . . C2 C 0.0003(3) 0.02733(12) 0.07779(11) 0.0227(5) Uani 1 1 d . . . C3 C -0.0132(3) 0.07761(12) 0.14163(11) 0.0254(5) Uani 1 1 d . . . H3 H -0.0302 0.0414 0.1790 0.030 Uiso 1 1 calc R . . C27 C -0.2533(4) -0.09973(12) -0.04745(11) 0.0276(5) Uani 1 1 d . . . H27 H -0.3027 -0.0523 -0.0639 0.033 Uiso 1 1 calc R . . C15 C -0.3210(4) 0.11044(14) -0.15474(12) 0.0352(7) Uani 1 1 d . . . H15 H -0.4291 0.1441 -0.1526 0.042 Uiso 1 1 calc R . . C5 C 0.2258(4) 0.17334(13) 0.09375(10) 0.0272(5) Uani 1 1 d . . . H5A H 0.1268 0.2145 0.0908 0.033 Uiso 1 1 calc R . . H5B H 0.3524 0.1984 0.1007 0.033 Uiso 1 1 calc R . . C24 C -0.1187(4) -0.23952(14) 0.00232(15) 0.0406(7) Uani 1 1 d . . . H24 H -0.0755 -0.2878 0.0190 0.049 Uiso 1 1 calc R . . C17 C -0.1270(4) 0.02325(15) -0.21609(12) 0.0363(6) Uani 1 1 d . . . H17 H -0.0998 -0.0029 -0.2555 0.044 Uiso 1 1 calc R . . C7 C -0.1851(4) 0.13365(13) 0.14118(12) 0.0306(6) Uani 1 1 d . . . H2A H -0.1702 0.1704 0.1047 0.037 Uiso 1 1 calc R . . H2B H -0.3049 0.1038 0.1339 0.037 Uiso 1 1 calc R . . C18 C -0.0067(4) 0.01111(13) -0.16188(11) 0.0290(6) Uani 1 1 d . . . C11 C 0.1440(4) -0.03352(13) 0.09158(12) 0.0265(5) Uani 1 1 d . . . C23 C -0.1348(4) -0.17611(13) 0.04318(14) 0.0330(6) Uani 1 1 d . . . H23 H -0.1015 -0.1802 0.0877 0.040 Uiso 1 1 calc R . . C14 C -0.2082(4) 0.10089(13) -0.10103(12) 0.0291(6) Uani 1 1 d . . . H14 H -0.2382 0.1285 -0.0625 0.035 Uiso 1 1 calc R . . C8 C -0.2042(4) 0.17893(14) 0.20345(12) 0.0357(7) Uani 1 1 d . . . C19 C 0.1508(4) -0.04031(14) -0.16573(13) 0.0370(7) Uani 1 1 d . . . H19 H 0.1775 -0.0659 -0.2055 0.044 Uiso 1 1 calc R . . C26 C -0.2325(4) -0.16336(13) -0.08763(12) 0.0357(6) Uani 1 1 d . . . H26 H -0.2641 -0.1594 -0.1323 0.043 Uiso 1 1 calc R . . C4 C 0.1801(3) 0.11962(13) 0.15052(12) 0.0284(6) Uani 1 1 d . . . H4A H 0.1761 0.1503 0.1910 0.034 Uiso 1 1 calc R . . H4B H 0.2842 0.0807 0.1548 0.034 Uiso 1 1 calc R . . C16 C -0.2807(4) 0.07161(14) -0.21291(12) 0.0380(7) Uani 1 1 d . . . H16 H -0.3605 0.0791 -0.2498 0.046 Uiso 1 1 calc R . . C21 C 0.2280(4) -0.01566(12) -0.05440(12) 0.0304(5) Uani 1 1 d . . . H21 H 0.3102 -0.0251 -0.0185 0.036 Uiso 1 1 calc R . . C25 C -0.1652(4) -0.23300(14) -0.06254(14) 0.0374(7) Uani 1 1 d . . . H25 H -0.1510 -0.2766 -0.0903 0.045 Uiso 1 1 calc R . . C9 C -0.3634(6) 0.2905(2) 0.24980(16) 0.0728(12) Uani 1 1 d . . . H9A H -0.2567 0.2875 0.2815 0.087 Uiso 1 1 calc R . . H9B H -0.3732 0.3446 0.2341 0.087 Uiso 1 1 calc R . . C10 C -0.5447(6) 0.2668(2) 0.28028(18) 0.0771(12) Uani 1 1 d . . . H10A H -0.6483 0.2680 0.2480 0.116 Uiso 1 1 calc R . . H10B H -0.5756 0.3025 0.3158 0.116 Uiso 1 1 calc R . . H10C H -0.5315 0.2141 0.2974 0.116 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 0.0248(3) 0.0246(3) 0.0255(3) 0.0017(2) -0.0001(3) -0.0011(3) O1 0.0355(10) 0.0385(9) 0.0244(8) 0.0049(7) 0.0011(8) -0.0067(9) O2 0.0240(9) 0.0302(8) 0.0337(9) 0.0026(7) -0.0041(7) 0.0058(8) O5 0.0673(14) 0.0513(12) 0.0285(11) -0.0048(9) -0.0009(10) 0.0186(11) O4 0.0435(12) 0.0509(11) 0.0515(12) 0.0072(9) 0.0206(11) -0.0050(10) N2 0.0360(13) 0.0245(9) 0.0288(11) -0.0022(8) 0.0051(12) -0.0079(11) C6 0.0282(14) 0.0189(9) 0.0249(12) 0.0026(8) 0.0010(12) 0.0020(11) C1 0.0233(13) 0.0204(11) 0.0232(13) 0.0014(9) -0.0007(11) 0.0042(10) O3 0.0593(14) 0.0447(11) 0.0521(13) 0.0240(10) 0.0134(11) 0.0189(11) C12 0.0242(14) 0.0224(11) 0.0269(13) -0.0015(10) 0.0006(10) -0.0033(10) C20 0.0367(16) 0.0316(13) 0.0427(15) -0.0106(11) 0.0021(14) 0.0066(13) C13 0.0309(14) 0.0208(11) 0.0259(13) 0.0009(9) 0.0013(11) -0.0050(10) O6 0.116(2) 0.0672(14) 0.0352(11) -0.0101(10) 0.0026(12) 0.0580(14) N1 0.0388(13) 0.0254(10) 0.0578(14) 0.0007(9) -0.0122(13) 0.0017(12) C22 0.0211(14) 0.0217(10) 0.0327(13) 0.0022(10) 0.0011(10) -0.0029(10) C2 0.0220(13) 0.0203(10) 0.0257(13) 0.0010(10) -0.0019(10) 0.0004(10) C3 0.0313(15) 0.0246(12) 0.0201(12) 0.0007(9) 0.0003(11) -0.0003(11) C27 0.0269(14) 0.0253(10) 0.0306(13) 0.0012(9) 0.0001(12) -0.0055(11) C15 0.0393(17) 0.0365(13) 0.0299(14) 0.0005(11) -0.0029(12) 0.0049(12) C5 0.0295(14) 0.0231(10) 0.0291(12) -0.0017(9) -0.0018(12) 0.0001(12) C24 0.0310(16) 0.0234(12) 0.067(2) 0.0016(12) -0.0045(14) -0.0017(11) C17 0.0476(17) 0.0351(14) 0.0262(13) -0.0064(11) 0.0003(12) -0.0040(14) C7 0.0366(17) 0.0293(12) 0.0259(13) 0.0000(10) 0.0014(11) 0.0040(11) C18 0.0367(16) 0.0249(12) 0.0253(13) -0.0015(10) 0.0025(11) -0.0058(11) C11 0.0273(14) 0.0204(12) 0.0318(14) 0.0011(10) -0.0031(11) -0.0023(12) C23 0.0287(15) 0.0264(12) 0.0439(15) 0.0061(11) -0.0060(12) -0.0054(11) C14 0.0343(16) 0.0256(11) 0.0274(13) 0.0003(10) 0.0006(11) 0.0017(11) C8 0.053(2) 0.0262(12) 0.0284(14) 0.0007(10) 0.0056(13) 0.0085(13) C19 0.0452(17) 0.0332(14) 0.0324(15) -0.0109(11) 0.0044(13) -0.0004(13) C26 0.0362(16) 0.0348(13) 0.0360(14) -0.0056(10) 0.0029(13) -0.0119(13) C4 0.0313(16) 0.0279(12) 0.0262(13) -0.0003(10) -0.0042(11) 0.0011(11) C16 0.0467(18) 0.0408(14) 0.0264(14) 0.0011(10) -0.0085(13) -0.0011(14) C21 0.0275(14) 0.0289(11) 0.0346(13) -0.0017(10) -0.0007(11) 0.0010(12) C25 0.0336(16) 0.0278(12) 0.0509(17) -0.0076(12) 0.0039(13) -0.0039(11) C9 0.106(3) 0.069(2) 0.0437(19) -0.0007(16) 0.021(2) 0.052(2) C10 0.108(3) 0.065(2) 0.059(2) -0.0112(18) -0.016(2) 0.024(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.4336(16) . ? S1 O2 1.4405(16) . ? S1 C22 1.758(2) . ? S1 C2 1.865(2) . ? O5 C8 1.192(3) . ? O4 N2 1.204(3) . ? N2 O3 1.219(3) . ? N2 C6 1.517(3) . ? C6 C5 1.522(3) . ? C6 C1 1.544(3) . ? C1 C12 1.528(3) . ? C1 C2 1.559(3) . ? C12 C21 1.385(3) . ? C12 C13 1.437(3) . ? C20 C19 1.363(4) . ? C20 C21 1.404(3) . ? C13 C14 1.423(3) . ? C13 C18 1.434(3) . ? O6 C8 1.327(3) . ? O6 C9 1.488(4) . ? N1 C11 1.146(3) . ? C22 C27 1.394(3) . ? C22 C23 1.395(3) . ? C2 C11 1.476(3) . ? C2 C3 1.580(3) . ? C3 C7 1.536(3) . ? C3 C4 1.537(3) . ? C27 C26 1.383(3) . ? C15 C14 1.367(3) . ? C15 C16 1.403(3) . ? C5 C4 1.527(3) . ? C24 C25 1.381(4) . ? C24 C23 1.386(4) . ? C17 C16 1.357(4) . ? C17 C18 1.412(4) . ? C7 C8 1.509(3) . ? C18 C19 1.411(4) . ? C26 C25 1.389(4) . ? C9 C10 1.465(5) . ? 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 120.35(11) . . ? O1 S1 C22 108.14(10) . . ? O2 S1 C22 108.18(10) . . ? O1 S1 C2 104.32(10) . . ? O2 S1 C2 105.58(10) . . ? C22 S1 C2 109.94(10) . . ? O4 N2 O3 123.6(2) . . ? O4 N2 C6 118.6(2) . . ? O3 N2 C6 117.9(2) . . ? N2 C6 C5 107.84(15) . . ? N2 C6 C1 106.58(18) . . ? C5 C6 C1 115.6(2) . . ? C12 C1 C6 108.84(18) . . ? C12 C1 C2 117.01(17) . . ? C6 C1 C2 109.26(18) . . ? C21 C12 C13 118.7(2) . . ? C21 C12 C1 119.6(2) . . ? C13 C12 C1 121.6(2) . . ? C19 C20 C21 120.1(2) . . ? C14 C13 C18 117.0(2) . . ? C14 C13 C12 124.3(2) . . ? C18 C13 C12 118.7(2) . . ? C8 O6 C9 118.2(2) . . ? C27 C22 C23 121.3(2) . . ? C27 C22 S1 118.74(16) . . ? C23 C22 S1 119.85(19) . . ? C11 C2 C1 114.08(19) . . ? C11 C2 C3 105.67(18) . . ? C1 C2 C3 111.99(17) . . ? C11 C2 S1 104.86(15) . . ? C1 C2 S1 112.10(15) . . ? C3 C2 S1 107.58(15) . . ? C7 C3 C4 112.51(18) . . ? C7 C3 C2 112.76(19) . . ? C4 C3 C2 107.84(18) . . ? C26 C27 C22 119.0(2) . . ? C14 C15 C16 121.4(2) . . ? C6 C5 C4 109.50(17) . . ? C25 C24 C23 120.4(2) . . ? C16 C17 C18 121.2(2) . . ? C8 C7 C3 112.9(2) . . ? C19 C18 C17 120.5(2) . . ? C19 C18 C13 119.6(2) . . ? C17 C18 C13 119.9(2) . . ? N1 C11 C2 176.2(3) . . ? C24 C23 C22 118.6(3) . . ? C15 C14 C13 121.0(2) . . ? O5 C8 O6 124.4(2) . . ? O5 C8 C7 126.3(2) . . ? O6 C8 C7 109.3(2) . . ? C20 C19 C18 120.9(2) . . ? C27 C26 C25 119.9(2) . . ? C5 C4 C3 112.1(2) . . ? C17 C16 C15 119.5(2) . . ? C12 C21 C20 122.1(2) . . ? C24 C25 C26 120.7(2) . . ? C10 C9 O6 107.6(3) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 60.83 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.264 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.039 #===END data_org_lett_3j _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 N2 O6 S' _chemical_formula_weight 470.53 _chemical_absolute_configuration ad 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 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.52030(10) _cell_length_b 11.50070(10) _cell_length_c 13.57270(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.4960(10) _cell_angle_gamma 90.00 _cell_volume 1154.24(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 27251 _cell_measurement_theta_min 3.3089 _cell_measurement_theta_max 62.1524 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.614 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8553 _exptl_absorpt_correction_T_max 0.8954 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; CheckCIF Alert THETM01_ALERT_3_B arises because of the restriction placed on the maximum two-theta achievable on the Gemini Enhance Ultra copper source when the Moly collimator is installed ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator 'mirror' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 36285 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36207 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0131 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 62.24 _reflns_number_total 3636 _reflns_number_gt 3578 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^ > 2\s(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. ; _publ_section_exptl_refinement ; ; _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^)+(0.0431P)^2^+0.1531P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.019(11) _refine_ls_number_reflns 3636 _refine_ls_number_parameters 300 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0243 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0649 _refine_ls_wR_factor_gt 0.0644 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.23670(5) 0.13588(3) 0.34094(3) 0.03098(10) Uani 1 1 d . . . O6 O 0.82798(16) 0.02002(11) 0.56635(8) 0.0388(3) Uani 1 1 d . . . O1 O 0.25109(15) 0.15921(10) 0.44591(8) 0.0397(3) Uani 1 1 d . . . O2 O 0.37188(16) 0.17817(10) 0.28818(10) 0.0404(3) Uani 1 1 d . . . O5 O 0.58829(18) -0.05173(13) 0.62180(9) 0.0494(3) Uani 1 1 d . . . O4 O 0.5678(2) -0.17821(15) 0.13775(12) 0.0635(4) Uani 1 1 d . . . N1 N -0.0697(2) -0.10765(14) 0.33988(12) 0.0461(4) Uani 1 1 d . . . C2 C 0.2517(2) -0.02693(13) 0.33213(12) 0.0290(3) Uani 1 1 d . . . O3 O 0.3797(3) -0.31953(16) 0.10602(14) 0.0787(5) Uani 1 1 d . . . C1 C 0.3245(2) -0.06440(14) 0.23650(12) 0.0310(3) Uani 1 1 d . . . H1 H 0.4483 -0.0303 0.2423 0.037 Uiso 1 1 calc R . . C21 C -0.2910(2) 0.30276(14) 0.19638(13) 0.0364(4) Uani 1 1 d . . . C19 C -0.0009(3) 0.22149(15) 0.18131(13) 0.0376(4) Uani 1 1 d . . . H19 H 0.0891 0.2062 0.1422 0.045 Uiso 1 1 calc R . . C18 C 0.0247(2) 0.18855(13) 0.28146(13) 0.0322(4) Uani 1 1 d . . . C3 C 0.3793(2) -0.06961(15) 0.42915(12) 0.0325(3) Uani 1 1 d . . . H3 H 0.3217 -0.0483 0.4875 0.039 Uiso 1 1 calc R . . C24 C -0.4605(3) 0.36606(18) 0.15065(15) 0.0465(4) Uani 1 1 d . . . H24A H -0.4287 0.4399 0.1222 0.070 Uiso 1 1 calc R . . H24B H -0.5331 0.3814 0.2023 0.070 Uiso 1 1 calc R . . H24C H -0.5304 0.3182 0.0975 0.070 Uiso 1 1 calc R . . C6 C 0.3474(2) -0.19731(15) 0.23863(13) 0.0369(4) Uani 1 1 d . . . H6 H 0.2252 -0.2343 0.2296 0.044 Uiso 1 1 calc R . . C22 C -0.2604(2) 0.27041(15) 0.29686(13) 0.0367(4) Uani 1 1 d . . . H22 H -0.3483 0.2885 0.3366 0.044 Uiso 1 1 calc R . . N2 N 0.4382(2) -0.23343(14) 0.15306(12) 0.0460(4) Uani 1 1 d . . . C20 C -0.1598(2) 0.27687(15) 0.13998(13) 0.0394(4) Uani 1 1 d . . . H20 H -0.1798 0.2978 0.0711 0.047 Uiso 1 1 calc R . . C12 C 0.2164(2) -0.02355(15) 0.13692(13) 0.0353(4) Uani 1 1 d . . . C5 C 0.4632(2) -0.24435(15) 0.33443(14) 0.0400(4) Uani 1 1 d . . . H5A H 0.4624 -0.3304 0.3328 0.048 Uiso 1 1 calc R . . H5B H 0.5897 -0.2179 0.3388 0.048 Uiso 1 1 calc R . . C23 C -0.1048(2) 0.21253(15) 0.33982(13) 0.0350(4) Uani 1 1 d . . . H23 H -0.0865 0.1894 0.4081 0.042 Uiso 1 1 calc R . . C11 C 0.0691(2) -0.07160(14) 0.33505(12) 0.0327(4) Uani 1 1 d . . . C4 C 0.3911(2) -0.20220(16) 0.42588(14) 0.0382(4) Uani 1 1 d . . . H4A H 0.4714 -0.2302 0.4873 0.046 Uiso 1 1 calc R . . H4B H 0.2694 -0.2356 0.4247 0.046 Uiso 1 1 calc R . . C7 C 0.5690(2) -0.01447(15) 0.44622(12) 0.0342(4) Uani 1 1 d . . . H7A H 0.6448 -0.0558 0.4050 0.041 Uiso 1 1 calc R . . H7B H 0.5590 0.0677 0.4242 0.041 Uiso 1 1 calc R . . C13 C 0.2991(3) 0.04870(17) 0.07650(13) 0.0427(4) Uani 1 1 d . . . H13 H 0.4217 0.0710 0.0978 0.051 Uiso 1 1 calc R . . C9 C 0.9277(2) 0.02083(16) 0.66853(13) 0.0405(4) Uani 1 1 d . . . H9A H 0.9436 -0.0596 0.6947 0.049 Uiso 1 1 calc R . . H9B H 0.8610 0.0660 0.7121 0.049 Uiso 1 1 calc R . . C10 C 1.1085(3) 0.07550(19) 0.66743(15) 0.0513(5) Uani 1 1 d . . . H10A H 1.1720 0.0313 0.6227 0.077 Uiso 1 1 calc R . . H10B H 1.1802 0.0751 0.7354 0.077 Uiso 1 1 calc R . . H10C H 1.0913 0.1558 0.6434 0.077 Uiso 1 1 calc R . . C17 C 0.0379(2) -0.05822(17) 0.10288(14) 0.0421(4) Uani 1 1 d . . . H17 H -0.0193 -0.1101 0.1417 0.050 Uiso 1 1 calc R . . C8 C 0.6585(2) -0.01975(14) 0.55388(13) 0.0333(4) Uani 1 1 d . . . C14 C 0.2046(3) 0.0885(2) -0.01431(14) 0.0537(5) Uani 1 1 d . . . H14 H 0.2626 0.1377 -0.0550 0.064 Uiso 1 1 calc R . . C15 C 0.0272(3) 0.0570(2) -0.04580(14) 0.0592(6) Uani 1 1 d . . . H15 H -0.0383 0.0859 -0.1074 0.071 Uiso 1 1 calc R . . C16 C -0.0560(3) -0.0166(2) 0.01198(15) 0.0543(5) Uani 1 1 d . . . H16 H -0.1783 -0.0390 -0.0105 0.065 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 0.02770(19) 0.02877(18) 0.03553(19) -0.00115(16) 0.00327(14) -0.00153(15) O6 0.0338(6) 0.0475(7) 0.0331(6) 0.0012(5) 0.0005(5) -0.0043(5) O1 0.0373(6) 0.0399(7) 0.0391(6) -0.0057(5) -0.0009(5) -0.0002(5) O2 0.0332(6) 0.0348(6) 0.0536(7) 0.0031(5) 0.0087(5) -0.0052(5) O5 0.0458(7) 0.0658(9) 0.0359(7) 0.0059(6) 0.0057(6) -0.0121(6) O4 0.0578(9) 0.0686(10) 0.0711(10) -0.0119(8) 0.0301(8) 0.0032(8) N1 0.0327(9) 0.0448(8) 0.0620(10) -0.0003(7) 0.0121(7) -0.0068(7) C2 0.0252(8) 0.0263(8) 0.0356(8) 0.0008(6) 0.0059(6) -0.0008(6) O3 0.0781(11) 0.0742(11) 0.0826(12) -0.0433(9) 0.0116(9) -0.0036(9) C1 0.0264(8) 0.0321(8) 0.0346(8) -0.0029(7) 0.0055(6) -0.0010(6) C21 0.0332(9) 0.0318(8) 0.0426(9) 0.0015(7) 0.0031(7) -0.0027(7) C19 0.0422(10) 0.0360(8) 0.0364(9) -0.0003(7) 0.0115(7) 0.0042(7) C18 0.0308(9) 0.0265(8) 0.0382(9) 0.0004(6) 0.0037(7) -0.0009(6) C3 0.0272(8) 0.0358(8) 0.0339(8) 0.0037(7) 0.0043(7) -0.0007(7) C24 0.0383(10) 0.0482(11) 0.0515(11) 0.0116(9) 0.0042(8) 0.0058(9) C6 0.0309(9) 0.0348(8) 0.0440(10) -0.0035(7) 0.0040(7) 0.0029(7) C22 0.0282(8) 0.0391(9) 0.0438(9) 0.0022(8) 0.0093(7) -0.0017(7) N2 0.0430(9) 0.0442(9) 0.0488(9) -0.0093(8) 0.0031(7) 0.0111(8) C20 0.0438(10) 0.0391(9) 0.0345(9) 0.0040(7) 0.0049(7) 0.0042(8) C12 0.0353(9) 0.0371(9) 0.0337(8) -0.0043(7) 0.0066(7) 0.0060(7) C5 0.0370(9) 0.0315(8) 0.0494(10) 0.0017(8) 0.0021(8) 0.0035(7) C23 0.0335(9) 0.0365(9) 0.0353(9) 0.0048(7) 0.0071(7) -0.0025(7) C11 0.0318(9) 0.0304(8) 0.0357(9) 0.0000(7) 0.0058(7) 0.0014(7) C4 0.0318(9) 0.0364(9) 0.0448(10) 0.0092(7) 0.0031(7) 0.0000(7) C7 0.0278(8) 0.0375(9) 0.0371(9) 0.0024(7) 0.0054(7) -0.0001(7) C13 0.0452(10) 0.0461(9) 0.0390(9) 0.0004(8) 0.0141(8) 0.0066(9) C9 0.0408(10) 0.0441(10) 0.0327(9) -0.0001(7) -0.0039(7) 0.0023(8) C10 0.0436(11) 0.0566(12) 0.0484(11) 0.0020(9) -0.0058(9) -0.0064(9) C17 0.0379(9) 0.0475(10) 0.0389(9) -0.0050(8) 0.0021(7) 0.0035(8) C8 0.0327(9) 0.0301(8) 0.0363(9) -0.0010(7) 0.0042(7) 0.0012(7) C14 0.0704(14) 0.0587(11) 0.0353(9) 0.0062(9) 0.0182(9) 0.0156(10) C15 0.0688(14) 0.0740(15) 0.0327(9) 0.0016(10) 0.0035(9) 0.0247(12) C16 0.0458(11) 0.0698(14) 0.0427(11) -0.0111(10) -0.0038(9) 0.0108(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 1.4311(12) . ? S1 O1 1.4343(12) . ? S1 C18 1.7582(17) . ? S1 C2 1.8810(16) . ? O6 C8 1.336(2) . ? O6 C9 1.452(2) . ? O5 C8 1.200(2) . ? O4 N2 1.213(2) . ? N1 C11 1.136(2) . ? C2 C11 1.474(2) . ? C2 C1 1.559(2) . ? C2 C3 1.560(2) . ? O3 N2 1.216(2) . ? C1 C12 1.519(2) . ? C1 C6 1.538(2) . ? C1 H1 1.0000 . ? C21 C20 1.387(3) . ? C21 C22 1.392(2) . ? C21 C24 1.501(2) . ? C19 C20 1.380(3) . ? C19 C18 1.390(2) . ? C19 H19 0.9500 . ? C18 C23 1.391(2) . ? C3 C4 1.529(2) . ? C3 C7 1.540(2) . ? C3 H3 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C6 N2 1.509(2) . ? C6 C5 1.526(2) . ? C6 H6 1.0000 . ? C22 C23 1.379(3) . ? C22 H22 0.9500 . ? C20 H20 0.9500 . ? C12 C13 1.391(3) . ? C12 C17 1.396(3) . ? C5 C4 1.522(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C23 H23 0.9500 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C7 C8 1.494(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C9 C10 1.500(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C17 C16 1.390(3) . ? C17 H17 0.9500 . ? C14 C15 1.374(3) . ? C14 H14 0.9500 . ? C15 C16 1.379(3) . ? C15 H15 0.9500 . ? C16 H16 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 O2 S1 O1 120.10(7) . . ? O2 S1 C18 108.69(8) . . ? O1 S1 C18 106.84(7) . . ? O2 S1 C2 104.49(7) . . ? O1 S1 C2 104.76(7) . . ? C18 S1 C2 111.94(7) . . ? C8 O6 C9 116.00(13) . . ? C11 C2 C1 113.36(13) . . ? C11 C2 C3 107.49(12) . . ? C1 C2 C3 111.13(12) . . ? C11 C2 S1 106.16(10) . . ? C1 C2 S1 111.25(10) . . ? C3 C2 S1 107.11(10) . . ? C12 C1 C6 111.35(13) . . ? C12 C1 C2 116.30(13) . . ? C6 C1 C2 108.31(13) . . ? C12 C1 H1 106.8 . . ? C6 C1 H1 106.8 . . ? C2 C1 H1 106.8 . . ? C20 C21 C22 118.44(16) . . ? C20 C21 C24 120.80(16) . . ? C22 C21 C24 120.75(16) . . ? C20 C19 C18 118.59(16) . . ? C20 C19 H19 120.7 . . ? C18 C19 H19 120.7 . . ? C19 C18 C23 121.08(15) . . ? C19 C18 S1 119.68(13) . . ? C23 C18 S1 118.53(13) . . ? C4 C3 C7 110.99(14) . . ? C4 C3 C2 108.62(13) . . ? C7 C3 C2 114.07(13) . . ? C4 C3 H3 107.6 . . ? C7 C3 H3 107.6 . . ? C2 C3 H3 107.6 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N2 C6 C5 106.87(14) . . ? N2 C6 C1 108.90(14) . . ? C5 C6 C1 114.38(14) . . ? N2 C6 H6 108.9 . . ? C5 C6 H6 108.9 . . ? C1 C6 H6 108.9 . . ? C23 C22 C21 121.29(16) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? O4 N2 O3 124.16(18) . . ? O4 N2 C6 118.57(15) . . ? O3 N2 C6 117.21(18) . . ? C19 C20 C21 121.68(16) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C13 C12 C17 118.79(17) . . ? C13 C12 C1 119.01(16) . . ? C17 C12 C1 122.18(15) . . ? C4 C5 C6 110.42(14) . . ? C4 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C22 C23 C18 118.89(16) . . ? C22 C23 H23 120.6 . . ? C18 C23 H23 120.6 . . ? N1 C11 C2 177.98(18) . . ? C5 C4 C3 111.88(14) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C8 C7 C3 111.72(13) . . ? C8 C7 H7A 109.3 . . ? C3 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C3 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C14 C13 C12 120.72(19) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? O6 C9 C10 107.74(15) . . ? O6 C9 H9A 110.2 . . ? C10 C9 H9A 110.2 . . ? O6 C9 H9B 110.2 . . ? C10 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C17 C12 119.85(18) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? O5 C8 O6 123.40(16) . . ? O5 C8 C7 125.51(16) . . ? O6 C8 C7 111.05(13) . . ? C15 C14 C13 120.1(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 120.03(19) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 120.4(2) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 62.24 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.150 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.028 #===END