# 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_d:\dyanne\2012\struct~1\007\sadabs\newp21c _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-6(-Methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)- pyridine-2-amine ; _chemical_name_common MMP _chemical_melting_point 467.5 _chemical_formula_moiety 'C18 H17 N3 O3 S' _chemical_formula_sum 'C18 H17 N3 O3 S' _chemical_formula_weight 355.41 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 14.0063(3) _cell_length_b 16.8616(4) _cell_length_c 7.8007(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.4020(10) _cell_angle_gamma 90.00 _cell_volume 1776.12(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3628 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 26.43 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9546 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method 'phi-, omega-scans of 1.0 deg' _diffrn_reflns_number 31335 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 26.43 _reflns_number_total 3628 _reflns_number_gt 2769 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT 2000' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2007)' _computing_molecular_graphics 'POV-ray for Windows v3.6' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0507P)^2^+0.6031P] 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 3628 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0913 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 S22 S 0.39051(3) 0.11566(3) 1.23841(5) 0.03660(14) Uani 1 1 d . . . O2 O -0.40514(9) 0.31746(7) 0.16337(19) 0.0476(3) Uani 1 1 d . . . O23 O 0.34687(10) 0.08648(8) 1.37248(16) 0.0509(4) Uani 1 1 d . . . O24 O 0.48098(9) 0.08028(7) 1.22250(16) 0.0436(3) Uani 1 1 d . . . N4 N -0.23477(10) 0.30746(8) 0.26247(19) 0.0372(3) Uani 1 1 d . . . C12 C 0.10238(12) 0.04057(10) 0.3954(2) 0.0342(4) Uani 1 1 d . . . H12 H 0.1598 0.0080 0.4230 0.041 Uiso 1 1 calc R . . N15 N -0.10078(11) 0.07129(8) 0.02366(18) 0.0405(4) Uani 1 1 d . . . H15A H -0.0840 0.0385 -0.0512 0.049 Uiso 1 1 calc R . . H15B H -0.1554 0.0995 -0.0108 0.049 Uiso 1 1 calc R . . C1 C -0.39337(15) 0.40216(11) 0.1811(3) 0.0579(6) Uani 1 1 d . . . H1A H -0.3610 0.4155 0.3053 0.087 Uiso 1 1 calc R . . H1B H -0.4585 0.4277 0.1453 0.087 Uiso 1 1 calc R . . H1C H -0.3526 0.4210 0.1050 0.087 Uiso 1 1 calc R . . C3 C -0.32170(12) 0.27293(10) 0.2015(2) 0.0351(4) Uani 1 1 d . . . C5 C -0.15482(12) 0.25972(10) 0.2955(2) 0.0351(4) Uani 1 1 d . . . H5 H -0.0916 0.2838 0.3380 0.042 Uiso 1 1 calc R . . C6 C -0.15753(12) 0.17869(9) 0.2725(2) 0.0303(4) Uani 1 1 d . . . C7 C -0.25171(12) 0.14475(10) 0.2111(2) 0.0374(4) Uani 1 1 d . . . H7 H -0.2582 0.0890 0.1949 0.045 Uiso 1 1 calc R . . C8 C -0.33410(13) 0.19154(10) 0.1745(2) 0.0403(4) Uani 1 1 d . . . H8 H -0.3983 0.1692 0.1317 0.048 Uiso 1 1 calc R . . C9 C -0.06537(12) 0.13107(9) 0.3169(2) 0.0314(4) Uani 1 1 d . . . C10 C 0.00244(12) 0.13723(10) 0.4812(2) 0.0337(4) Uani 1 1 d . . . H10 H -0.0105 0.1729 0.5665 0.040 Uiso 1 1 calc R . . C11 C 0.08967(12) 0.09237(10) 0.5255(2) 0.0323(4) Uani 1 1 d . . . N13 N 0.03962(10) 0.03315(8) 0.23365(17) 0.0340(3) Uani 1 1 d . . . C14 C -0.04254(12) 0.07833(9) 0.1917(2) 0.0310(4) Uani 1 1 d . . . C16 C 0.16323(12) 0.09845(10) 0.7011(2) 0.0321(4) Uani 1 1 d . . . C17 C 0.26273(12) 0.08113(10) 0.7189(2) 0.0344(4) Uani 1 1 d . . . H17 H 0.2833 0.0659 0.6170 0.041 Uiso 1 1 calc R . . C18 C 0.33227(12) 0.08573(10) 0.8827(2) 0.0338(4) Uani 1 1 d . . . H18 H 0.3997 0.0732 0.8931 0.041 Uiso 1 1 calc R . . C19 C 0.30229(12) 0.10878(9) 1.0309(2) 0.0322(4) Uani 1 1 d . . . C20 C 0.20375(13) 0.12594(11) 1.0168(2) 0.0403(4) Uani 1 1 d . . . H20 H 0.1835 0.1415 1.1189 0.048 Uiso 1 1 calc R . . C21 C 0.13528(13) 0.12031(11) 0.8532(2) 0.0405(4) Uani 1 1 d . . . H21 H 0.0677 0.1316 0.8441 0.049 Uiso 1 1 calc R . . C25 C 0.41024(15) 0.21803(11) 1.2746(3) 0.0501(5) Uani 1 1 d . . . H25A H 0.3481 0.2436 1.2789 0.075 Uiso 1 1 calc R . . H25B H 0.4334 0.2410 1.1774 0.075 Uiso 1 1 calc R . . H25C H 0.4602 0.2266 1.3876 0.075 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 S22 0.0401(3) 0.0435(3) 0.0248(2) 0.00129(17) 0.00608(17) -0.00663(19) O2 0.0333(6) 0.0378(7) 0.0656(9) -0.0051(6) 0.0023(6) 0.0056(5) O23 0.0524(8) 0.0723(9) 0.0285(7) 0.0094(6) 0.0117(6) -0.0088(7) O24 0.0376(7) 0.0515(8) 0.0384(7) 0.0008(6) 0.0041(5) -0.0025(6) N4 0.0327(8) 0.0316(7) 0.0447(9) -0.0061(6) 0.0057(6) -0.0006(6) C12 0.0350(9) 0.0372(9) 0.0296(8) 0.0002(7) 0.0072(7) 0.0049(7) N15 0.0478(9) 0.0409(8) 0.0276(7) -0.0056(6) 0.0009(6) 0.0169(7) C1 0.0505(12) 0.0374(11) 0.0738(15) -0.0071(10) -0.0044(11) 0.0112(9) C3 0.0310(9) 0.0351(9) 0.0378(9) -0.0026(7) 0.0066(7) 0.0011(7) C5 0.0287(8) 0.0356(9) 0.0391(10) -0.0059(7) 0.0060(7) -0.0022(7) C6 0.0325(8) 0.0319(9) 0.0271(8) -0.0025(6) 0.0087(7) -0.0007(7) C7 0.0395(9) 0.0291(8) 0.0434(10) -0.0026(7) 0.0106(8) -0.0040(7) C8 0.0306(9) 0.0368(10) 0.0514(11) -0.0053(8) 0.0068(8) -0.0063(7) C9 0.0340(9) 0.0302(8) 0.0301(9) -0.0016(6) 0.0088(7) -0.0001(7) C10 0.0351(9) 0.0373(9) 0.0293(8) -0.0062(7) 0.0093(7) 0.0001(7) C11 0.0348(9) 0.0362(9) 0.0261(8) -0.0014(7) 0.0083(7) -0.0006(7) N13 0.0380(8) 0.0349(8) 0.0269(7) -0.0028(6) 0.0048(6) 0.0066(6) C14 0.0363(9) 0.0296(8) 0.0263(8) -0.0006(6) 0.0067(7) 0.0019(7) C16 0.0351(9) 0.0345(9) 0.0259(8) -0.0018(7) 0.0069(7) -0.0011(7) C17 0.0387(9) 0.0396(9) 0.0261(8) -0.0028(7) 0.0109(7) -0.0014(7) C18 0.0321(8) 0.0387(9) 0.0303(9) 0.0004(7) 0.0080(7) -0.0032(7) C19 0.0365(9) 0.0342(9) 0.0252(8) 0.0006(7) 0.0068(7) -0.0053(7) C20 0.0407(10) 0.0534(11) 0.0283(9) -0.0078(8) 0.0118(8) -0.0025(8) C21 0.0344(9) 0.0554(12) 0.0314(9) -0.0060(8) 0.0085(7) 0.0013(8) C25 0.0599(12) 0.0481(11) 0.0391(10) -0.0123(9) 0.0076(9) -0.0101(9) _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 S22 O23 1.4314(13) . ? S22 O24 1.4353(13) . ? S22 C25 1.7590(19) . ? S22 C19 1.7603(16) . ? O2 C3 1.354(2) . ? O2 C1 1.440(2) . ? N4 C3 1.319(2) . ? N4 C5 1.347(2) . ? C12 N13 1.338(2) . ? C12 C11 1.386(2) . ? C12 H12 0.9500 . ? N15 C14 1.352(2) . ? N15 H15A 0.8800 . ? N15 H15B 0.8800 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3 C8 1.392(2) . ? C5 C6 1.377(2) . ? C5 H5 0.9500 . ? C6 C7 1.400(2) . ? C6 C9 1.481(2) . ? C7 C8 1.364(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.381(2) . ? C9 C14 1.419(2) . ? C10 C11 1.400(2) . ? C10 H10 0.9500 . ? C11 C16 1.483(2) . ? N13 C14 1.346(2) . ? C16 C21 1.394(2) . ? C16 C17 1.394(2) . ? C17 C18 1.388(2) . ? C17 H17 0.9500 . ? C18 C19 1.386(2) . ? C18 H18 0.9500 . ? C19 C20 1.386(2) . ? C20 C21 1.381(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? 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 O23 S22 O24 118.58(8) . . ? O23 S22 C25 107.42(9) . . ? O24 S22 C25 108.48(9) . . ? O23 S22 C19 108.53(8) . . ? O24 S22 C19 108.25(8) . . ? C25 S22 C19 104.73(9) . . ? C3 O2 C1 117.30(14) . . ? C3 N4 C5 116.48(14) . . ? N13 C12 C11 124.70(15) . . ? N13 C12 H12 117.6 . . ? C11 C12 H12 117.6 . . ? C14 N15 H15A 120.0 . . ? C14 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N4 C3 O2 119.65(15) . . ? N4 C3 C8 123.76(15) . . ? O2 C3 C8 116.59(15) . . ? N4 C5 C6 125.11(15) . . ? N4 C5 H5 117.4 . . ? C6 C5 H5 117.4 . . ? C5 C6 C7 116.16(15) . . ? C5 C6 C9 121.01(14) . . ? C7 C6 C9 122.80(15) . . ? C8 C7 C6 120.19(16) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C3 118.29(15) . . ? C7 C8 H8 120.9 . . ? C3 C8 H8 120.9 . . ? C10 C9 C14 117.43(15) . . ? C10 C9 C6 121.21(14) . . ? C14 C9 C6 121.35(14) . . ? C9 C10 C11 121.89(15) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C12 C11 C10 115.67(15) . . ? C12 C11 C16 121.82(15) . . ? C10 C11 C16 122.50(14) . . ? C12 N13 C14 118.79(13) . . ? N13 C14 N15 116.27(14) . . ? N13 C14 C9 121.44(14) . . ? N15 C14 C9 122.28(14) . . ? C21 C16 C17 118.02(15) . . ? C21 C16 C11 121.42(15) . . ? C17 C16 C11 120.55(14) . . ? C18 C17 C16 121.22(15) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C17 119.31(16) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 120.57(15) . . ? C18 C19 S22 119.43(13) . . ? C20 C19 S22 119.99(13) . . ? C21 C20 C19 119.41(16) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C16 121.45(16) . . ? C20 C21 H21 119.3 . . ? C16 C21 H21 119.3 . . ? S22 C25 H25A 109.5 . . ? S22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N4 C3 O2 -179.21(15) . . . . ? C5 N4 C3 C8 1.5(3) . . . . ? C1 O2 C3 N4 4.0(2) . . . . ? C1 O2 C3 C8 -176.66(17) . . . . ? C3 N4 C5 C6 -0.8(3) . . . . ? N4 C5 C6 C7 -0.5(3) . . . . ? N4 C5 C6 C9 -178.46(15) . . . . ? C5 C6 C7 C8 1.2(3) . . . . ? C9 C6 C7 C8 179.11(16) . . . . ? C6 C7 C8 C3 -0.6(3) . . . . ? N4 C3 C8 C7 -0.8(3) . . . . ? O2 C3 C8 C7 179.86(16) . . . . ? C5 C6 C9 C10 52.0(2) . . . . ? C7 C6 C9 C10 -125.77(18) . . . . ? C5 C6 C9 C14 -126.96(18) . . . . ? C7 C6 C9 C14 55.2(2) . . . . ? C14 C9 C10 C11 -1.3(2) . . . . ? C6 C9 C10 C11 179.71(15) . . . . ? N13 C12 C11 C10 2.1(2) . . . . ? N13 C12 C11 C16 -178.95(15) . . . . ? C9 C10 C11 C12 -1.2(2) . . . . ? C9 C10 C11 C16 179.89(16) . . . . ? C11 C12 N13 C14 -0.4(2) . . . . ? C12 N13 C14 N15 176.80(15) . . . . ? C12 N13 C14 C9 -2.3(2) . . . . ? C10 C9 C14 N13 3.1(2) . . . . ? C6 C9 C14 N13 -177.88(15) . . . . ? C10 C9 C14 N15 -175.96(15) . . . . ? C6 C9 C14 N15 3.1(2) . . . . ? C12 C11 C16 C21 -151.09(17) . . . . ? C10 C11 C16 C21 27.8(2) . . . . ? C12 C11 C16 C17 27.9(2) . . . . ? C10 C11 C16 C17 -153.20(16) . . . . ? C21 C16 C17 C18 -0.3(2) . . . . ? C11 C16 C17 C18 -179.30(15) . . . . ? C16 C17 C18 C19 -0.7(2) . . . . ? C17 C18 C19 C20 1.0(2) . . . . ? C17 C18 C19 S22 -179.35(12) . . . . ? O23 S22 C19 C18 -140.75(14) . . . . ? O24 S22 C19 C18 -10.82(16) . . . . ? C25 S22 C19 C18 104.76(15) . . . . ? O23 S22 C19 C20 38.92(16) . . . . ? O24 S22 C19 C20 168.84(14) . . . . ? C25 S22 C19 C20 -75.57(16) . . . . ? C18 C19 C20 C21 -0.3(3) . . . . ? S22 C19 C20 C21 180.00(14) . . . . ? C19 C20 C21 C16 -0.6(3) . . . . ? C17 C16 C21 C20 0.9(3) . . . . ? C11 C16 C21 C20 179.96(17) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.213 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 959474' ####################################################################### # # 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_d:\dyanne\2012\struct~1\007adi~1\007adiap1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-6(-Methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)- pyridine-2-amine. hexanedioic acid ; _chemical_name_common ? _chemical_melting_point 417 _chemical_formula_moiety '2(C18 H17 N3 O3 S1), C6 H10 O4' _chemical_formula_sum 'C42 H44 N6 O10 S2' _chemical_formula_weight 856.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4542(7) _cell_length_b 10.7365(7) _cell_length_c 19.2796(12) _cell_angle_alpha 92.4070(10) _cell_angle_beta 96.173(2) _cell_angle_gamma 105.2470(10) _cell_volume 2070.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7830 _cell_measurement_theta_min 1.97 _cell_measurement_theta_max 25.70 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 0.195 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9431 _exptl_absorpt_correction_T_max 0.9777 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II Duo diffractometer' _diffrn_measurement_method 'phi- and omega-scans of 0.5 deg.' _diffrn_reflns_number 20933 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.70 _reflns_number_total 7830 _reflns_number_gt 5045 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXH-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury (Macrae at al., 2006) and POV-RAY (Cason, 2003) ; _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0574P)^2^+1.1805P] 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 7830 _refine_ls_number_parameters 551 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0918 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1131 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 1.001 _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 S22A S 0.78388(8) 0.31577(8) -0.08025(4) 0.0365(2) Uani 1 1 d . . . S22B S 0.73363(8) 0.79207(7) -0.08508(3) 0.03053(19) Uani 1 1 d . . . O1C O 0.68199(19) 0.40448(17) 0.49587(9) 0.0306(5) Uani 1 1 d . . . O2A O 0.0823(2) -0.36052(19) 0.32197(10) 0.0406(5) Uani 1 1 d . . . O2B O 0.0770(2) 0.12928(19) 0.32072(10) 0.0415(5) Uani 1 1 d . . . O3C O 0.8144(2) 0.45897(18) 0.41298(10) 0.0376(5) Uani 1 1 d . . . H3C H 0.7636 0.3901 0.3928 0.045 Uiso 1 1 calc R . . O9C O 1.32273(19) 1.09548(17) 0.50444(9) 0.0307(5) Uani 1 1 d . . . O10C O 1.18523(19) 1.04838(18) 0.58575(9) 0.0339(5) Uani 1 1 d . . . H10C H 1.2387 1.1152 0.6066 0.041 Uiso 1 1 calc R . . O23A O 0.6681(2) 0.2581(3) -0.12931(11) 0.0570(7) Uani 1 1 d . . . O23B O 0.6334(2) 0.69628(19) -0.13006(10) 0.0393(5) Uani 1 1 d . . . O24A O 0.8450(3) 0.4534(2) -0.07856(12) 0.0644(8) Uani 1 1 d . . . O24B O 0.7435(2) 0.92699(19) -0.09351(10) 0.0416(5) Uani 1 1 d . . . N4A N 0.1689(2) -0.1776(2) 0.26474(11) 0.0318(6) Uani 1 1 d . . . N4B N 0.1576(2) 0.3190(2) 0.26790(11) 0.0320(6) Uani 1 1 d . . . N13A N 0.6724(2) 0.2593(2) 0.33259(11) 0.0300(5) Uani 1 1 d . . . N13B N 0.6699(2) 0.7517(2) 0.33429(11) 0.0261(5) Uani 1 1 d . . . N15A N 0.55884(18) 0.14196(18) 0.41390(10) 0.0266(5) Uani 1 1 d D . . N15B N 0.55363(19) 0.63993(18) 0.41892(9) 0.0270(5) Uani 1 1 d D . . C1A C -0.0409(4) -0.3744(4) 0.27830(19) 0.0686(12) Uani 1 1 d . . . H1A1 H -0.0602 -0.2900 0.2761 0.103 Uiso 1 1 calc R . . H1A2 H -0.1132 -0.4352 0.2977 0.103 Uiso 1 1 calc R . . H1A3 H -0.0337 -0.4074 0.2311 0.103 Uiso 1 1 calc R . . C1B C -0.0478(4) 0.1141(4) 0.27860(19) 0.0742(14) Uani 1 1 d . . . H1B1 H -0.0678 0.1981 0.2765 0.111 Uiso 1 1 calc R . . H1B2 H -0.1186 0.0534 0.2992 0.111 Uiso 1 1 calc R . . H1B3 H -0.0427 0.0803 0.2313 0.111 Uiso 1 1 calc R . . C2C C 0.7775(3) 0.4787(2) 0.47446(13) 0.0242(6) Uani 1 1 d . . . C3A C 0.1841(3) -0.2564(2) 0.31384(13) 0.0273(6) Uani 1 1 d . . . C3B C 0.1763(3) 0.2368(2) 0.31445(14) 0.0282(6) Uani 1 1 d . . . C4C C 0.8634(3) 0.5974(2) 0.51655(13) 0.0280(6) Uani 1 1 d . . . H4C1 H 0.9157 0.5697 0.5560 0.034 Uiso 1 1 calc R . . H4C2 H 0.8043 0.6439 0.5367 0.034 Uiso 1 1 calc R . . C5A C 0.2747(3) -0.0758(3) 0.25999(14) 0.0292(6) Uani 1 1 d . . . H5A H 0.2660 -0.0185 0.2247 0.035 Uiso 1 1 calc R . . C5B C 0.2604(3) 0.4235(3) 0.26456(14) 0.0291(6) Uani 1 1 d . . . H5B H 0.2486 0.4837 0.2314 0.035 Uiso 1 1 calc R . . C5C C 0.9602(3) 0.6921(2) 0.47723(13) 0.0266(6) Uani 1 1 d . . . H5C1 H 0.9091 0.7213 0.4379 0.032 Uiso 1 1 calc R . . H5C2 H 1.0208 0.6472 0.4574 0.032 Uiso 1 1 calc R . . C6A C 0.3947(3) -0.0491(2) 0.30275(13) 0.0235(6) Uani 1 1 d . . . C6B C 0.3824(3) 0.4497(2) 0.30604(13) 0.0228(6) Uani 1 1 d . . . C6C C 1.0432(3) 0.8099(2) 0.52408(13) 0.0272(6) Uani 1 1 d . . . H6C1 H 0.9826 0.8548 0.5442 0.033 Uiso 1 1 calc R . . H6C2 H 1.0948 0.7809 0.5633 0.033 Uiso 1 1 calc R . . C7A C 0.4054(3) -0.1348(2) 0.35465(13) 0.0261(6) Uani 1 1 d . . . H7A H 0.4856 -0.1199 0.3858 0.031 Uiso 1 1 calc R . . C7B C 0.3963(3) 0.3606(2) 0.35567(13) 0.0246(6) Uani 1 1 d . . . H7B H 0.4771 0.3751 0.3863 0.030 Uiso 1 1 calc R . . C7C C 1.1388(3) 0.9043(2) 0.48430(13) 0.0271(6) Uani 1 1 d . . . H7C1 H 1.1979 0.8578 0.4641 0.033 Uiso 1 1 calc R . . H7C2 H 1.0858 0.9310 0.4448 0.033 Uiso 1 1 calc R . . C8A C 0.3005(3) -0.2396(3) 0.36046(14) 0.0283(6) Uani 1 1 d . . . H8A H 0.3066 -0.2991 0.3950 0.034 Uiso 1 1 calc R . . C8B C 0.2934(3) 0.2529(3) 0.35981(14) 0.0282(6) Uani 1 1 d . . . H8B H 0.3016 0.1911 0.3926 0.034 Uiso 1 1 calc R . . C8C C 1.2251(3) 1.0244(2) 0.52568(13) 0.0244(6) Uani 1 1 d . . . C9A C 0.5062(3) 0.0627(2) 0.29056(13) 0.0223(6) Uani 1 1 d . . . C9B C 0.4938(3) 0.5611(2) 0.29353(13) 0.0220(6) Uani 1 1 d . . . C10A C 0.5396(3) 0.0840(2) 0.22381(13) 0.0249(6) Uani 1 1 d . . . H10A H 0.4939 0.0229 0.1863 0.030 Uiso 1 1 calc R . . C10B C 0.5213(3) 0.5839(2) 0.22610(13) 0.0245(6) Uani 1 1 d . . . H10B H 0.4700 0.5258 0.1886 0.029 Uiso 1 1 calc R . . C11A C 0.6390(3) 0.1929(2) 0.20971(13) 0.0253(6) Uani 1 1 d . . . C11B C 0.6227(3) 0.6904(2) 0.21131(13) 0.0251(6) Uani 1 1 d . . . C12A C 0.6995(3) 0.2774(3) 0.26658(14) 0.0324(7) Uani 1 1 d . . . H12A H 0.7650 0.3538 0.2587 0.039 Uiso 1 1 calc R . . C12B C 0.6931(3) 0.7706(3) 0.26783(13) 0.0281(6) Uani 1 1 d . . . H12B H 0.7621 0.8438 0.2594 0.034 Uiso 1 1 calc R . . C14A C 0.5789(3) 0.1538(2) 0.34591(13) 0.0234(6) Uani 1 1 d . . . C14B C 0.5728(3) 0.6502(2) 0.34853(13) 0.0222(6) Uani 1 1 d . . . C16A C 0.6767(3) 0.2202(2) 0.13852(13) 0.0262(6) Uani 1 1 d . . . C16B C 0.6535(3) 0.7154(2) 0.13900(13) 0.0250(6) Uani 1 1 d . . . C17A C 0.7954(3) 0.3107(3) 0.12896(15) 0.0355(7) Uani 1 1 d . . . H17A H 0.8557 0.3518 0.1688 0.043 Uiso 1 1 calc R . . C17B C 0.7000(3) 0.8414(3) 0.11963(14) 0.0307(7) Uani 1 1 d . . . H17B H 0.7128 0.9119 0.1534 0.037 Uiso 1 1 calc R . . C18A C 0.8275(3) 0.3422(3) 0.06286(15) 0.0365(7) Uani 1 1 d . . . H18A H 0.9073 0.4064 0.0576 0.044 Uiso 1 1 calc R . . C18B C 0.7280(3) 0.8660(3) 0.05215(14) 0.0322(7) Uani 1 1 d . . . H18B H 0.7604 0.9524 0.0399 0.039 Uiso 1 1 calc R . . C19A C 0.7429(3) 0.2796(3) 0.00468(14) 0.0288(6) Uani 1 1 d . . . C19B C 0.7080(3) 0.7625(3) 0.00256(13) 0.0269(6) Uani 1 1 d . . . C20A C 0.6267(3) 0.1865(3) 0.01258(15) 0.0362(7) Uani 1 1 d . . . H20A H 0.5695 0.1419 -0.0275 0.043 Uiso 1 1 calc R . . C20B C 0.6621(3) 0.6363(3) 0.02056(14) 0.0320(7) Uani 1 1 d . . . H20B H 0.6488 0.5660 -0.0134 0.038 Uiso 1 1 calc R . . C21A C 0.5939(3) 0.1582(3) 0.07893(14) 0.0341(7) Uani 1 1 d . . . H21A H 0.5132 0.0950 0.0838 0.041 Uiso 1 1 calc R . . C21B C 0.6359(3) 0.6134(3) 0.08837(14) 0.0307(7) Uani 1 1 d . . . H21B H 0.6053 0.5267 0.1007 0.037 Uiso 1 1 calc R . . C25A C 0.9081(3) 0.2378(3) -0.09294(14) 0.0362(7) Uani 1 1 d . . . H25A H 0.9288 0.2448 -0.1412 0.054 Uiso 1 1 calc R . . H25B H 0.8762 0.1463 -0.0840 0.054 Uiso 1 1 calc R . . H25C H 0.9888 0.2788 -0.0607 0.054 Uiso 1 1 calc R . . C25B C 0.8940(2) 0.7654(3) -0.09631(13) 0.0402(8) Uani 1 1 d . . . H25D H 0.8936 0.6771 -0.0851 0.060 Uiso 1 1 calc R . . H25E H 0.9641 0.8274 -0.0650 0.060 Uiso 1 1 calc R . . H25F H 0.9113 0.7771 -0.1449 0.060 Uiso 1 1 calc R . . H15A H 0.4824 0.0901 0.4222 0.037(8) Uiso 1 1 d RD . . H15C H 0.4772 0.5833 0.4256 0.061(11) Uiso 1 1 d RD . . H15B H 0.6007 0.2114 0.4412 0.026(7) Uiso 1 1 d RD . . H15D H 0.6030 0.7123 0.4433 0.071(12) Uiso 1 1 d RD . . 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 S22A 0.0460(5) 0.0429(5) 0.0256(4) 0.0133(3) 0.0121(3) 0.0159(4) S22B 0.0410(5) 0.0294(4) 0.0192(4) 0.0041(3) 0.0063(3) 0.0046(3) O1C 0.0337(11) 0.0289(10) 0.0227(10) 0.0019(8) 0.0060(8) -0.0040(9) O2A 0.0407(13) 0.0332(11) 0.0381(12) 0.0015(9) 0.0118(10) -0.0099(10) O2B 0.0422(13) 0.0329(11) 0.0378(12) 0.0010(9) 0.0116(10) -0.0127(10) O3C 0.0413(13) 0.0312(11) 0.0274(11) -0.0126(9) 0.0141(9) -0.0143(9) O9C 0.0338(11) 0.0292(10) 0.0227(10) 0.0011(8) 0.0063(8) -0.0035(9) O10C 0.0368(12) 0.0294(11) 0.0252(11) -0.0102(8) 0.0090(9) -0.0094(9) O23A 0.0396(14) 0.107(2) 0.0276(12) 0.0165(12) 0.0021(10) 0.0240(14) O23B 0.0454(13) 0.0415(12) 0.0228(10) -0.0053(9) -0.0010(9) 0.0010(10) O24A 0.107(2) 0.0405(14) 0.0548(15) 0.0226(12) 0.0398(15) 0.0218(14) O24B 0.0596(15) 0.0338(12) 0.0317(12) 0.0122(9) 0.0122(10) 0.0091(10) N4A 0.0311(14) 0.0352(14) 0.0209(12) 0.0015(10) 0.0029(10) -0.0051(11) N4B 0.0301(14) 0.0331(13) 0.0233(12) 0.0018(10) 0.0016(10) -0.0073(11) N13A 0.0327(14) 0.0280(13) 0.0233(12) -0.0031(10) 0.0083(10) -0.0036(11) N13B 0.0277(13) 0.0258(12) 0.0199(12) -0.0024(9) 0.0042(10) -0.0013(10) N15A 0.0297(14) 0.0238(12) 0.0201(12) -0.0033(10) 0.0019(10) -0.0026(11) N15B 0.0286(13) 0.0262(12) 0.0211(12) 0.0018(10) 0.0013(10) -0.0011(11) C1A 0.050(2) 0.075(3) 0.051(2) 0.016(2) -0.0015(19) -0.033(2) C1B 0.050(2) 0.086(3) 0.052(2) 0.017(2) -0.0068(19) -0.039(2) C2C 0.0269(15) 0.0241(14) 0.0196(14) 0.0021(11) 0.0020(11) 0.0034(12) C3A 0.0309(16) 0.0244(14) 0.0223(14) -0.0039(12) 0.0108(12) -0.0023(12) C3B 0.0317(17) 0.0227(14) 0.0250(15) -0.0040(12) 0.0111(12) -0.0038(12) C4C 0.0305(16) 0.0264(15) 0.0227(14) -0.0031(12) 0.0041(12) 0.0006(12) C5A 0.0317(17) 0.0295(15) 0.0210(14) 0.0033(12) 0.0022(12) -0.0007(13) C5B 0.0324(17) 0.0299(15) 0.0211(14) 0.0047(12) 0.0037(12) 0.0013(13) C5C 0.0297(16) 0.0224(14) 0.0223(14) -0.0034(11) 0.0025(12) -0.0013(12) C6A 0.0279(15) 0.0215(14) 0.0185(13) -0.0025(11) 0.0055(11) 0.0014(12) C6B 0.0281(15) 0.0201(13) 0.0191(13) -0.0014(11) 0.0056(11) 0.0039(11) C6C 0.0314(16) 0.0240(14) 0.0225(14) -0.0021(11) 0.0030(12) 0.0018(12) C7A 0.0279(16) 0.0262(15) 0.0235(14) 0.0015(11) 0.0029(12) 0.0060(12) C7B 0.0267(15) 0.0243(14) 0.0225(14) -0.0001(11) 0.0033(11) 0.0063(12) C7C 0.0286(16) 0.0259(15) 0.0220(14) -0.0030(11) 0.0042(12) -0.0010(12) C8A 0.0354(17) 0.0237(14) 0.0283(15) 0.0049(12) 0.0104(13) 0.0093(13) C8B 0.0361(17) 0.0238(14) 0.0261(15) 0.0042(12) 0.0105(13) 0.0077(13) C8C 0.0274(15) 0.0257(14) 0.0185(14) 0.0045(11) 0.0016(11) 0.0044(12) C9A 0.0238(15) 0.0207(13) 0.0204(14) -0.0002(11) 0.0014(11) 0.0036(11) C9B 0.0239(15) 0.0196(13) 0.0209(14) 0.0014(11) 0.0020(11) 0.0036(11) C10A 0.0263(15) 0.0241(14) 0.0216(14) -0.0017(11) 0.0014(11) 0.0032(12) C10B 0.0267(15) 0.0225(14) 0.0212(14) -0.0015(11) 0.0012(11) 0.0022(12) C11A 0.0239(15) 0.0248(14) 0.0242(14) -0.0014(11) 0.0052(11) 0.0006(12) C11B 0.0280(15) 0.0234(14) 0.0212(14) 0.0022(11) 0.0045(11) 0.0016(12) C12A 0.0343(17) 0.0278(15) 0.0285(16) -0.0011(12) 0.0110(13) -0.0055(13) C12B 0.0301(16) 0.0247(14) 0.0238(15) 0.0004(12) 0.0072(12) -0.0037(12) C14A 0.0253(15) 0.0239(14) 0.0206(14) 0.0009(11) 0.0041(11) 0.0058(12) C14B 0.0232(14) 0.0208(13) 0.0214(14) 0.0011(11) 0.0028(11) 0.0037(11) C16A 0.0275(16) 0.0250(14) 0.0246(15) -0.0002(12) 0.0076(12) 0.0027(12) C16B 0.0268(15) 0.0254(14) 0.0197(14) 0.0003(11) 0.0049(11) 0.0010(12) C17A 0.0349(18) 0.0366(17) 0.0264(15) -0.0022(13) 0.0064(13) -0.0058(14) C17B 0.0399(18) 0.0243(15) 0.0224(14) -0.0027(12) 0.0056(12) -0.0009(13) C18A 0.0346(18) 0.0360(17) 0.0337(17) 0.0040(14) 0.0129(14) -0.0034(14) C18B 0.0400(18) 0.0246(15) 0.0265(15) 0.0036(12) 0.0059(13) -0.0018(13) C19A 0.0327(17) 0.0310(15) 0.0239(15) 0.0055(12) 0.0074(12) 0.0087(13) C19B 0.0309(16) 0.0266(15) 0.0206(14) 0.0013(11) 0.0055(12) 0.0025(12) C20A 0.0350(18) 0.0440(18) 0.0238(15) -0.0001(13) 0.0022(13) 0.0015(14) C20B 0.0444(18) 0.0256(15) 0.0224(15) -0.0008(12) 0.0074(13) 0.0021(13) C21A 0.0313(17) 0.0350(16) 0.0281(16) -0.0001(13) 0.0062(13) -0.0054(13) C21B 0.0418(18) 0.0222(14) 0.0247(15) 0.0017(12) 0.0080(13) 0.0010(13) C25A 0.0381(18) 0.0456(18) 0.0238(15) 0.0040(13) 0.0065(13) 0.0080(15) C25B 0.0429(19) 0.0462(19) 0.0299(17) 0.0028(14) 0.0074(14) 0.0080(15) _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 S22A O23A 1.433(2) . ? S22A O24A 1.445(2) . ? S22A C25A 1.752(3) . ? S22A C19A 1.770(3) . ? S22B O23B 1.439(2) . ? S22B O24B 1.442(2) . ? S22B C19B 1.768(3) . ? S22B C25B 1.807(2) . ? O1C C2C 1.225(3) . ? O2A C3A 1.353(3) . ? O2A C1A 1.430(4) . ? O2B C3B 1.353(3) . ? O2B C1B 1.428(4) . ? O3C C2C 1.311(3) . ? O3C H3C 0.8400 . ? O9C C8C 1.224(3) . ? O10C C8C 1.310(3) . ? O10C H10C 0.8400 . ? N4A C3A 1.320(3) . ? N4A C5A 1.350(3) . ? N4B C3B 1.320(3) . ? N4B C5B 1.344(3) . ? N13A C14A 1.342(3) . ? N13A C12A 1.344(3) . ? N13B C14B 1.340(3) . ? N13B C12B 1.343(3) . ? N15A C14A 1.355(3) . ? N15A H15A 0.8807 . ? N15A H15B 0.8781 . ? N15B C14B 1.398(3) . ? N15B H15C 0.8936 . ? N15B H15D 0.8926 . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C1B H1B1 0.9800 . ? C1B H1B2 0.9800 . ? C1B H1B3 0.9800 . ? C2C C4C 1.498(4) . ? C3A C8A 1.399(4) . ? C3B C8B 1.393(4) . ? C4C C5C 1.524(3) . ? C4C H4C1 0.9900 . ? C4C H4C2 0.9900 . ? C5A C6A 1.380(4) . ? C5A H5A 0.9500 . ? C5B C6B 1.385(4) . ? C5B H5B 0.9500 . ? C5C C6C 1.525(4) . ? C5C H5C1 0.9900 . ? C5C H5C2 0.9900 . ? C6A C7A 1.402(3) . ? C6A C9A 1.484(3) . ? C6B C7B 1.404(3) . ? C6B C9B 1.482(3) . ? C6C C7C 1.521(3) . ? C6C H6C1 0.9900 . ? C6C H6C2 0.9900 . ? C7A C8A 1.367(4) . ? C7A H7A 0.9500 . ? C7B C8B 1.368(4) . ? C7B H7B 0.9500 . ? C7C C8C 1.503(4) . ? C7C H7C1 0.9900 . ? C7C H7C2 0.9900 . ? C8A H8A 0.9500 . ? C8B H8B 0.9500 . ? C9A C10A 1.382(3) . ? C9A C14A 1.421(4) . ? C9B C10B 1.379(3) . ? C9B C14B 1.426(4) . ? C10A C11A 1.403(3) . ? C10A H10A 0.9500 . ? C10B C11B 1.403(3) . ? C10B H10B 0.9500 . ? C11A C12A 1.375(4) . ? C11A C16A 1.488(3) . ? C11B C12B 1.373(4) . ? C11B C16B 1.484(3) . ? C12A H12A 0.9500 . ? C12B H12B 0.9500 . ? C16A C21A 1.390(4) . ? C16A C17A 1.396(4) . ? C16B C17B 1.393(4) . ? C16B C21B 1.397(4) . ? C17A C18A 1.386(4) . ? C17A H17A 0.9500 . ? C17B C18B 1.385(4) . ? C17B H17B 0.9500 . ? C18A C19A 1.380(4) . ? C18A H18A 0.9500 . ? C18B C19B 1.392(4) . ? C18B H18B 0.9500 . ? C19A C20A 1.383(4) . ? C19B C20B 1.386(4) . ? C20A C21A 1.385(4) . ? C20A H20A 0.9500 . ? C20B C21B 1.383(3) . ? C20B H20B 0.9500 . ? C21A H21A 0.9500 . ? C21B H21B 0.9500 . ? C25A H25A 0.9800 . ? C25A H25B 0.9800 . ? C25A H25C 0.9800 . ? C25B H25D 0.9800 . ? C25B H25E 0.9800 . ? C25B H25F 0.9800 . ? 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 O23A S22A O24A 119.39(15) . . ? O23A S22A C25A 108.97(15) . . ? O24A S22A C25A 107.25(15) . . ? O23A S22A C19A 108.06(13) . . ? O24A S22A C19A 107.62(14) . . ? C25A S22A C19A 104.58(13) . . ? O23B S22B O24B 118.56(13) . . ? O23B S22B C19B 108.11(12) . . ? O24B S22B C19B 107.80(12) . . ? O23B S22B C25B 107.64(14) . . ? O24B S22B C25B 107.77(13) . . ? C19B S22B C25B 106.33(13) . . ? C3A O2A C1A 116.8(2) . . ? C3B O2B C1B 117.5(2) . . ? C2C O3C H3C 109.5 . . ? C8C O10C H10C 109.5 . . ? C3A N4A C5A 116.4(2) . . ? C3B N4B C5B 116.6(2) . . ? C14A N13A C12A 119.7(2) . . ? C14B N13B C12B 120.1(2) . . ? C14A N15A H15A 116.8 . . ? C14A N15A H15B 113.4 . . ? H15A N15A H15B 122.5 . . ? C14B N15B H15C 113.6 . . ? C14B N15B H15D 108.6 . . ? H15C N15B H15D 132.4 . . ? O2A C1A H1A1 109.5 . . ? O2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? O2A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? O2B C1B H1B1 109.5 . . ? O2B C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? O2B C1B H1B3 109.5 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? O1C C2C O3C 122.4(2) . . ? O1C C2C C4C 123.1(2) . . ? O3C C2C C4C 114.5(2) . . ? N4A C3A O2A 119.9(3) . . ? N4A C3A C8A 124.3(2) . . ? O2A C3A C8A 115.8(2) . . ? N4B C3B O2B 119.8(3) . . ? N4B C3B C8B 124.3(2) . . ? O2B C3B C8B 115.9(2) . . ? C2C C4C C5C 116.0(2) . . ? C2C C4C H4C1 108.3 . . ? C5C C4C H4C1 108.3 . . ? C2C C4C H4C2 108.3 . . ? C5C C4C H4C2 108.3 . . ? H4C1 C4C H4C2 107.4 . . ? N4A C5A C6A 124.7(2) . . ? N4A C5A H5A 117.7 . . ? C6A C5A H5A 117.7 . . ? N4B C5B C6B 124.7(2) . . ? N4B C5B H5B 117.7 . . ? C6B C5B H5B 117.7 . . ? C4C C5C C6C 112.4(2) . . ? C4C C5C H5C1 109.1 . . ? C6C C5C H5C1 109.1 . . ? C4C C5C H5C2 109.1 . . ? C6C C5C H5C2 109.1 . . ? H5C1 C5C H5C2 107.9 . . ? C5A C6A C7A 116.8(2) . . ? C5A C6A C9A 119.8(2) . . ? C7A C6A C9A 123.4(2) . . ? C5B C6B C7B 116.5(2) . . ? C5B C6B C9B 120.3(2) . . ? C7B C6B C9B 123.0(2) . . ? C7C C6C C5C 112.0(2) . . ? C7C C6C H6C1 109.2 . . ? C5C C6C H6C1 109.2 . . ? C7C C6C H6C2 109.2 . . ? C5C C6C H6C2 109.2 . . ? H6C1 C6C H6C2 107.9 . . ? C8A C7A C6A 120.1(3) . . ? C8A C7A H7A 120.0 . . ? C6A C7A H7A 120.0 . . ? C8B C7B C6B 119.9(3) . . ? C8B C7B H7B 120.0 . . ? C6B C7B H7B 120.0 . . ? C8C C7C C6C 116.3(2) . . ? C8C C7C H7C1 108.2 . . ? C6C C7C H7C1 108.2 . . ? C8C C7C H7C2 108.2 . . ? C6C C7C H7C2 108.2 . . ? H7C1 C7C H7C2 107.4 . . ? C7A C8A C3A 117.8(2) . . ? C7A C8A H8A 121.1 . . ? C3A C8A H8A 121.1 . . ? C7B C8B C3B 118.0(2) . . ? C7B C8B H8B 121.0 . . ? C3B C8B H8B 121.0 . . ? O9C C8C O10C 122.7(2) . . ? O9C C8C C7C 122.9(2) . . ? O10C C8C C7C 114.4(2) . . ? C10A C9A C14A 117.7(2) . . ? C10A C9A C6A 120.5(2) . . ? C14A C9A C6A 121.8(2) . . ? C10B C9B C14B 117.5(2) . . ? C10B C9B C6B 119.7(2) . . ? C14B C9B C6B 122.7(2) . . ? C9A C10A C11A 122.1(2) . . ? C9A C10A H10A 119.0 . . ? C11A C10A H10A 119.0 . . ? C9B C10B C11B 121.9(2) . . ? C9B C10B H10B 119.0 . . ? C11B C10B H10B 119.0 . . ? C12A C11A C10A 115.5(2) . . ? C12A C11A C16A 120.7(2) . . ? C10A C11A C16A 123.7(2) . . ? C12B C11B C10B 116.1(2) . . ? C12B C11B C16B 121.5(2) . . ? C10B C11B C16B 122.3(2) . . ? N13A C12A C11A 124.5(2) . . ? N13A C12A H12A 117.8 . . ? C11A C12A H12A 117.8 . . ? N13B C12B C11B 123.9(2) . . ? N13B C12B H12B 118.1 . . ? C11B C12B H12B 118.1 . . ? N13A C14A N15A 116.0(2) . . ? N13A C14A C9A 120.5(2) . . ? N15A C14A C9A 123.5(2) . . ? N13B C14B N15B 116.2(2) . . ? N13B C14B C9B 120.5(2) . . ? N15B C14B C9B 123.3(2) . . ? C21A C16A C17A 117.4(2) . . ? C21A C16A C11A 121.2(2) . . ? C17A C16A C11A 121.3(2) . . ? C17B C16B C21B 118.2(2) . . ? C17B C16B C11B 120.9(2) . . ? C21B C16B C11B 121.0(2) . . ? C18A C17A C16A 121.7(3) . . ? C18A C17A H17A 119.2 . . ? C16A C17A H17A 119.2 . . ? C18B C17B C16B 121.4(3) . . ? C18B C17B H17B 119.3 . . ? C16B C17B H17B 119.3 . . ? C19A C18A C17A 119.5(3) . . ? C19A C18A H18A 120.2 . . ? C17A C18A H18A 120.2 . . ? C17B C18B C19B 119.2(2) . . ? C17B C18B H18B 120.4 . . ? C19B C18B H18B 120.4 . . ? C18A C19A C20A 120.0(2) . . ? C18A C19A S22A 120.3(2) . . ? C20A C19A S22A 119.7(2) . . ? C20B C19B C18B 120.5(2) . . ? C20B C19B S22B 119.5(2) . . ? C18B C19B S22B 119.9(2) . . ? C19A C20A C21A 120.0(3) . . ? C19A C20A H20A 120.0 . . ? C21A C20A H20A 120.0 . . ? C21B C20B C19B 119.5(3) . . ? C21B C20B H20B 120.2 . . ? C19B C20B H20B 120.2 . . ? C20A C21A C16A 121.4(3) . . ? C20A C21A H21A 119.3 . . ? C16A C21A H21A 119.3 . . ? C20B C21B C16B 121.2(2) . . ? C20B C21B H21B 119.4 . . ? C16B C21B H21B 119.4 . . ? S22A C25A H25A 109.5 . . ? S22A C25A H25B 109.5 . . ? H25A C25A H25B 109.5 . . ? S22A C25A H25C 109.5 . . ? H25A C25A H25C 109.5 . . ? H25B C25A H25C 109.5 . . ? S22B C25B H25D 109.5 . . ? S22B C25B H25E 109.5 . . ? H25D C25B H25E 109.5 . . ? S22B C25B H25F 109.5 . . ? H25D C25B H25F 109.5 . . ? H25E C25B H25F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5A N4A C3A O2A 179.8(2) . . . . ? C5A N4A C3A C8A 0.7(4) . . . . ? C1A O2A C3A N4A -3.6(4) . . . . ? C1A O2A C3A C8A 175.6(3) . . . . ? C5B N4B C3B O2B -180.0(2) . . . . ? C5B N4B C3B C8B 0.8(4) . . . . ? C1B O2B C3B N4B -3.6(4) . . . . ? C1B O2B C3B C8B 175.6(3) . . . . ? O1C C2C C4C C5C -168.5(2) . . . . ? O3C C2C C4C C5C 12.7(4) . . . . ? C3A N4A C5A C6A -0.6(4) . . . . ? C3B N4B C5B C6B 0.1(4) . . . . ? C2C C4C C5C C6C 179.9(2) . . . . ? N4A C5A C6A C7A -0.2(4) . . . . ? N4A C5A C6A C9A 177.4(2) . . . . ? N4B C5B C6B C7B -1.3(4) . . . . ? N4B C5B C6B C9B 174.1(2) . . . . ? C4C C5C C6C C7C -179.7(2) . . . . ? C5A C6A C7A C8A 0.8(4) . . . . ? C9A C6A C7A C8A -176.6(2) . . . . ? C5B C6B C7B C8B 1.7(4) . . . . ? C9B C6B C7B C8B -173.6(2) . . . . ? C5C C6C C7C C8C 179.7(2) . . . . ? C6A C7A C8A C3A -0.7(4) . . . . ? N4A C3A C8A C7A -0.1(4) . . . . ? O2A C3A C8A C7A -179.2(2) . . . . ? C6B C7B C8B C3B -0.9(4) . . . . ? N4B C3B C8B C7B -0.4(4) . . . . ? O2B C3B C8B C7B -179.7(2) . . . . ? C6C C7C C8C O9C 165.7(2) . . . . ? C6C C7C C8C O10C -15.9(4) . . . . ? C5A C6A C9A C10A -46.0(4) . . . . ? C7A C6A C9A C10A 131.3(3) . . . . ? C5A C6A C9A C14A 131.7(3) . . . . ? C7A C6A C9A C14A -51.0(4) . . . . ? C5B C6B C9B C10B -44.3(4) . . . . ? C7B C6B C9B C10B 130.8(3) . . . . ? C5B C6B C9B C14B 133.6(3) . . . . ? C7B C6B C9B C14B -51.3(4) . . . . ? C14A C9A C10A C11A -1.7(4) . . . . ? C6A C9A C10A C11A 176.1(2) . . . . ? C14B C9B C10B C11B -0.1(4) . . . . ? C6B C9B C10B C11B 177.9(2) . . . . ? C9A C10A C11A C12A -0.7(4) . . . . ? C9A C10A C11A C16A -179.1(3) . . . . ? C9B C10B C11B C12B 0.0(4) . . . . ? C9B C10B C11B C16B 179.7(3) . . . . ? C14A N13A C12A C11A -1.2(4) . . . . ? C10A C11A C12A N13A 2.3(4) . . . . ? C16A C11A C12A N13A -179.2(3) . . . . ? C14B N13B C12B C11B -0.5(4) . . . . ? C10B C11B C12B N13B 0.3(4) . . . . ? C16B C11B C12B N13B -179.4(3) . . . . ? C12A N13A C14A N15A 179.2(2) . . . . ? C12A N13A C14A C9A -1.4(4) . . . . ? C10A C9A C14A N13A 2.8(4) . . . . ? C6A C9A C14A N13A -174.9(2) . . . . ? C10A C9A C14A N15A -177.8(2) . . . . ? C6A C9A C14A N15A 4.4(4) . . . . ? C12B N13B C14B N15B -178.5(2) . . . . ? C12B N13B C14B C9B 0.4(4) . . . . ? C10B C9B C14B N13B -0.1(4) . . . . ? C6B C9B C14B N13B -178.0(2) . . . . ? C10B C9B C14B N15B 178.6(2) . . . . ? C6B C9B C14B N15B 0.7(4) . . . . ? C12A C11A C16A C21A -161.7(3) . . . . ? C10A C11A C16A C21A 16.7(4) . . . . ? C12A C11A C16A C17A 17.3(4) . . . . ? C10A C11A C16A C17A -164.4(3) . . . . ? C12B C11B C16B C17B -32.4(4) . . . . ? C10B C11B C16B C17B 147.9(3) . . . . ? C12B C11B C16B C21B 148.0(3) . . . . ? C10B C11B C16B C21B -31.7(4) . . . . ? C21A C16A C17A C18A 2.8(4) . . . . ? C11A C16A C17A C18A -176.2(3) . . . . ? C21B C16B C17B C18B 0.2(4) . . . . ? C11B C16B C17B C18B -179.4(3) . . . . ? C16A C17A C18A C19A -2.3(5) . . . . ? C16B C17B C18B C19B 0.6(4) . . . . ? C17A C18A C19A C20A 0.1(5) . . . . ? C17A C18A C19A S22A -178.6(2) . . . . ? O23A S22A C19A C18A -168.3(2) . . . . ? O24A S22A C19A C18A -38.1(3) . . . . ? C25A S22A C19A C18A 75.7(3) . . . . ? O23A S22A C19A C20A 13.0(3) . . . . ? O24A S22A C19A C20A 143.2(2) . . . . ? C25A S22A C19A C20A -103.0(3) . . . . ? C17B C18B C19B C20B -0.7(4) . . . . ? C17B C18B C19B S22B 176.3(2) . . . . ? O23B S22B C19B C20B 34.6(3) . . . . ? O24B S22B C19B C20B 163.9(2) . . . . ? C25B S22B C19B C20B -80.7(3) . . . . ? O23B S22B C19B C18B -142.4(2) . . . . ? O24B S22B C19B C18B -13.1(3) . . . . ? C25B S22B C19B C18B 102.2(3) . . . . ? C18A C19A C20A C21A 1.5(5) . . . . ? S22A C19A C20A C21A -179.7(2) . . . . ? C18B C19B C20B C21B 0.1(4) . . . . ? S22B C19B C20B C21B -176.9(2) . . . . ? C19A C20A C21A C16A -1.0(5) . . . . ? C17A C16A C21A C20A -1.1(4) . . . . ? C11A C16A C21A C20A 177.9(3) . . . . ? C19B C20B C21B C16B 0.7(5) . . . . ? C17B C16B C21B C20B -0.8(4) . . . . ? C11B C16B C21B C20B 178.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.70 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.725 _refine_diff_density_min -0.688 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 959475' ####################################################################### # # 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_c:\dyanne~1\2012\struct~1\007fap1_\bath\new _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-6(-Methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)- pyridine-2-amine.(E)-butenedioate methanolate ; _chemical_name_common ? _chemical_melting_point 460 _chemical_formula_moiety 'C18 H18 N3 O3 S, C4 H3 O4, C1 H4 O' _chemical_formula_sum 'C23 H25 N3 O8 S' _chemical_formula_weight 503.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.411(2) _cell_length_b 11.572(5) _cell_length_c 18.486(8) _cell_angle_alpha 87.456(8) _cell_angle_beta 89.447(7) _cell_angle_gamma 84.076(8) _cell_volume 1150.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4859 _cell_measurement_theta_min 1.77 _cell_measurement_theta_max 26.73 _exptl_crystal_description blocks _exptl_crystal_colour 'translucent yellow' _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9190 _exptl_absorpt_correction_T_max 0.9619 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II Duo diffractometer' _diffrn_measurement_method 'phi- and omega-scans of 0.5 deg.' _diffrn_reflns_number 23376 _diffrn_reflns_av_R_equivalents 0.0847 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.73 _reflns_number_total 4859 _reflns_number_gt 3835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXH-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury (Macrae at al., 2006) and POV-RAY (Cason, 2003) ; _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.1003P)^2^+5.4392P] 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 4859 _refine_ls_number_parameters 312 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_gt 0.1079 _refine_ls_wR_factor_ref 0.2707 _refine_ls_wR_factor_gt 0.2590 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.035 _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 S22 S 0.8999(2) 0.63783(11) 0.63925(6) 0.0316(3) Uani 1 1 d . . . O2 O 0.1667(8) 0.3372(4) 0.06011(18) 0.0486(10) Uani 1 1 d D . . O23 O 0.7878(7) 0.5342(3) 0.65756(18) 0.0421(9) Uani 1 1 d . . . O24 O 1.1546(7) 0.6426(4) 0.6590(2) 0.0472(10) Uani 1 1 d . . . O26A O 1.3148(16) 0.9121(7) 0.1396(3) 0.0239(17) Uiso 0.536(17) 1 d PD A 2 O28B O 1.2340(17) 0.8464(7) 0.0317(3) 0.029(2) Uiso 0.464(17) 1 d PD A 1 O30 O 0.4960(7) 0.9646(3) 0.3698(2) 0.0432(9) Uani 1 1 d . . . H30 H 0.5199 0.9838 0.3261 0.052 Uiso 1 1 calc R . . O32 O 0.8653(8) 1.0271(4) 0.3861(2) 0.0534(11) Uani 1 1 d . . . O34 O 1.5610(9) 1.0080(5) 0.2357(2) 0.0639(13) Uani 1 1 d . . . H34 H 1.4873 0.9839 0.2005 0.077 Uiso 1 1 calc R . . N4A N 0.4141(10) 0.3787(5) 0.1531(3) 0.0321(13) Uiso 0.722(7) 1 d P B 1 N13 N 0.9742(8) 0.7866(3) 0.20505(19) 0.0312(9) Uani 1 1 d . B . H13 H 1.0671 0.8348 0.1822 0.037 Uiso 1 1 calc R . . N15 N 0.8467(9) 0.7392(4) 0.0943(2) 0.0484(13) Uani 1 1 d . B . H15A H 0.9402 0.7901 0.0746 0.058 Uiso 1 1 calc R . . H15B H 0.7592 0.6990 0.0666 0.058 Uiso 1 1 calc R . . N4B N 0.194(3) 0.4509(13) 0.1519(9) 0.054(5) Uiso 0.278(7) 1 d PD B 2 C3 C 0.2989(9) 0.4089(5) 0.0961(2) 0.0357(11) Uani 1 1 d D B . C7B C 0.646(4) 0.5074(16) 0.1011(11) 0.052(5) Uiso 0.278(7) 1 d PD B 2 H7B H 0.8045 0.5224 0.0827 0.062 Uiso 0.278(7) 1 calc PR B 2 C5A C 0.5439(12) 0.4529(5) 0.1857(3) 0.0286(14) Uiso 0.722(7) 1 d P B 1 H5A H 0.6355 0.4257 0.2277 0.034 Uiso 0.722(7) 1 calc PR B 1 C6 C 0.5529(8) 0.5646(4) 0.1624(2) 0.0275(9) Uani 1 1 d D . . C7A C 0.4118(11) 0.6039(5) 0.0999(3) 0.0279(13) Uiso 0.722(7) 1 d P B 1 H7A H 0.4082 0.6825 0.0824 0.033 Uiso 0.722(7) 1 calc PR B 1 C8A C 0.2822(11) 0.5286(5) 0.0655(3) 0.0260(13) Uiso 0.722(7) 1 d P B 1 H8A H 0.1857 0.5521 0.0237 0.031 Uiso 0.722(7) 1 calc PR B 1 C9 C 0.6936(8) 0.6431(4) 0.2025(2) 0.0267(9) Uani 1 1 d . B . C10 C 0.7023(8) 0.6369(4) 0.2764(2) 0.0267(9) Uani 1 1 d . . . H10 H 0.6076 0.5833 0.3018 0.032 Uiso 1 1 calc R B . C11 C 0.8446(8) 0.7059(4) 0.3166(2) 0.0275(9) Uani 1 1 d . B . C12 C 0.9772(9) 0.7807(4) 0.2780(2) 0.0316(10) Uani 1 1 d . . . H12 H 1.0742 0.8300 0.3029 0.038 Uiso 1 1 calc R B . C14 C 0.8376(8) 0.7232(4) 0.1657(2) 0.0290(9) Uani 1 1 d . . . C16 C 0.8522(8) 0.6950(4) 0.3966(2) 0.0273(9) Uani 1 1 d . . . C17 C 1.0350(9) 0.7409(5) 0.4346(3) 0.0389(12) Uani 1 1 d . B . H17 H 1.1530 0.7832 0.4094 0.047 Uiso 1 1 calc R . . C18 C 1.0467(10) 0.7254(5) 0.5089(3) 0.0401(12) Uani 1 1 d . . . H18 H 1.1720 0.7576 0.5348 0.048 Uiso 1 1 calc R B . C19 C 0.8784(8) 0.6639(4) 0.5453(2) 0.0278(9) Uani 1 1 d . B . C20 C 0.6906(10) 0.6203(5) 0.5088(2) 0.0400(12) Uani 1 1 d . . . H20 H 0.5713 0.5793 0.5343 0.048 Uiso 1 1 calc R B . C21 C 0.6783(10) 0.6370(5) 0.4345(2) 0.0421(13) Uani 1 1 d . B . H21 H 0.5477 0.6082 0.4089 0.050 Uiso 1 1 calc R . . C25 C 0.7199(10) 0.7562(5) 0.6754(2) 0.0376(11) Uani 1 1 d . . . H25A H 0.5480 0.7578 0.6588 0.056 Uiso 1 1 calc R . . H25B H 0.7870 0.8285 0.6593 0.056 Uiso 1 1 calc R . . H25C H 0.7238 0.7484 0.7284 0.056 Uiso 1 1 calc R . . C5B C 0.325(3) 0.5275(14) 0.1852(10) 0.042(5) Uiso 0.278(7) 1 d PD B 2 H5B H 0.2552 0.5590 0.2284 0.051 Uiso 0.278(7) 1 calc PR B 2 C27 C 1.3083(8) 0.9223(4) 0.0707(2) 0.0352(10) Uiso 1 1 d D . . C8B C 0.516(5) 0.4302(19) 0.0665(14) 0.072(7) Uiso 0.278(7) 1 d PD B 2 H8B H 0.5770 0.3941 0.0239 0.087 Uiso 0.278(7) 1 calc PR B 2 C29A C 1.5086(18) 0.9837(8) 0.0358(4) 0.018(2) Uiso 0.536(17) 1 d PD . 2 H29A H 1.6474 1.0002 0.0632 0.022 Uiso 0.536(17) 1 calc PR A 2 C31 C 0.6735(10) 0.9984(5) 0.4096(3) 0.0394(11) Uani 1 1 d . . . C33 C 0.6142(9) 0.9999(5) 0.4872(3) 0.0402(11) Uani 1 1 d . . . H33 H 0.7464 1.0008 0.5205 0.048 Uiso 1 1 calc R . . C35 C 1.7294(12) 1.0865(6) 0.2101(4) 0.0560(16) Uani 1 1 d . . . H35A H 1.6379 1.1527 0.1839 0.084 Uiso 1 1 calc R . . H35B H 1.8507 1.0468 0.1774 0.084 Uiso 1 1 calc R . . H35C H 1.8162 1.1143 0.2511 0.084 Uiso 1 1 calc R . . C1B C 0.036(4) 0.2552(16) 0.1029(7) 0.051(5) Uiso 0.43(3) 1 d PD C 2 H1B1 H 0.1465 0.2167 0.1402 0.076 Uiso 0.43(3) 1 calc PR C 2 H1B2 H -0.0193 0.1969 0.0715 0.076 Uiso 0.43(3) 1 calc PR C 2 H1B3 H -0.1093 0.2966 0.1260 0.076 Uiso 0.43(3) 1 calc PR C 2 C1A C 0.142(3) 0.2293(8) 0.0952(5) 0.036(3) Uiso 0.57(3) 1 d PD C 1 H1A1 H 0.3062 0.1871 0.1030 0.054 Uiso 0.57(3) 1 calc PR C 1 H1A2 H 0.0423 0.1840 0.0653 0.054 Uiso 0.57(3) 1 calc PR C 1 H1A3 H 0.0584 0.2414 0.1420 0.054 Uiso 0.57(3) 1 calc PR C 1 O28A O 1.1394(16) 0.8871(8) 0.0352(4) 0.042(2) Uiso 0.536(17) 1 d PD A 2 O26B O 1.244(2) 0.9385(9) 0.1354(3) 0.031(2) Uiso 0.464(17) 1 d PD A 1 C29B C 1.442(3) 1.0071(12) 0.0323(7) 0.041(4) Uiso 0.464(17) 1 d PD . 1 H29B H 1.4499 1.0794 0.0541 0.049 Uiso 0.464(17) 1 calc PR A 1 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 S22 0.0330(6) 0.0391(7) 0.0229(5) 0.0032(4) -0.0068(4) -0.0057(5) O2 0.056(2) 0.065(3) 0.0296(17) -0.0097(17) -0.0092(16) -0.025(2) O23 0.052(2) 0.043(2) 0.0317(17) 0.0081(15) -0.0024(15) -0.0120(17) O24 0.038(2) 0.063(3) 0.0394(19) 0.0089(17) -0.0115(16) -0.0048(18) O30 0.037(2) 0.053(2) 0.0409(19) -0.0007(17) -0.0017(15) -0.0122(17) O32 0.041(2) 0.076(3) 0.046(2) 0.001(2) 0.0014(17) -0.021(2) O34 0.061(3) 0.098(4) 0.042(2) -0.002(2) -0.004(2) -0.051(3) N13 0.039(2) 0.035(2) 0.0215(17) 0.0021(15) 0.0044(15) -0.0156(17) N15 0.064(3) 0.064(3) 0.0228(19) 0.0115(19) -0.0113(19) -0.039(3) C3 0.034(3) 0.053(3) 0.022(2) -0.0085(19) -0.0050(18) -0.016(2) C6 0.025(2) 0.036(2) 0.0223(19) 0.0010(17) -0.0011(16) -0.0072(18) C9 0.024(2) 0.031(2) 0.024(2) 0.0022(16) 0.0010(16) -0.0030(17) C10 0.027(2) 0.029(2) 0.025(2) 0.0022(16) -0.0005(16) -0.0067(17) C11 0.030(2) 0.032(2) 0.0218(19) -0.0017(16) 0.0014(16) -0.0074(18) C12 0.034(2) 0.039(3) 0.024(2) -0.0050(18) 0.0015(17) -0.012(2) C14 0.030(2) 0.035(2) 0.0223(19) 0.0034(17) -0.0035(16) -0.0061(18) C16 0.031(2) 0.030(2) 0.022(2) -0.0027(16) 0.0002(16) -0.0081(18) C17 0.035(3) 0.057(3) 0.028(2) 0.004(2) 0.0002(19) -0.021(2) C18 0.040(3) 0.056(3) 0.027(2) 0.002(2) -0.006(2) -0.020(2) C19 0.031(2) 0.033(2) 0.0200(19) -0.0012(16) -0.0016(16) -0.0015(18) C20 0.043(3) 0.057(3) 0.024(2) -0.001(2) 0.003(2) -0.029(2) C21 0.047(3) 0.063(3) 0.022(2) -0.007(2) 0.001(2) -0.032(3) C25 0.045(3) 0.044(3) 0.024(2) -0.0049(19) -0.0015(19) -0.004(2) C31 0.034(3) 0.042(3) 0.042(3) -0.002(2) -0.005(2) -0.006(2) C33 0.031(2) 0.049(3) 0.041(3) 0.000(2) -0.007(2) -0.005(2) C35 0.050(4) 0.066(4) 0.057(4) -0.002(3) 0.002(3) -0.031(3) _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 S22 O23 1.425(4) . ? S22 O24 1.436(4) . ? S22 C25 1.750(5) . ? S22 C19 1.753(4) . ? O2 C3 1.351(6) . ? O2 C1A 1.400(7) . ? O2 C1B 1.446(9) . ? O26A C27 1.274(6) . ? O28B C27 1.259(6) . ? O30 C31 1.318(6) . ? O30 H30 0.8400 . ? O32 C31 1.194(6) . ? O34 C35 1.416(7) . ? O34 H34 0.8400 . ? N4A C3 1.248(7) . ? N4A C5A 1.331(8) . ? N13 C14 1.336(6) . ? N13 C12 1.348(5) . ? N13 H13 0.8800 . ? N15 C14 1.325(6) . ? N15 H15A 0.8800 . ? N15 H15B 0.8800 . ? N4B C3 1.264(19) . ? N4B C5B 1.36(3) . ? C3 C8B 1.33(3) . ? C3 C8A 1.467(8) . ? C7B C8B 1.37(3) . ? C7B C6 1.40(2) . ? C7B H7B 0.9500 . ? C5A C6 1.349(8) . ? C5A H5A 0.9500 . ? C6 C5B 1.40(2) . ? C6 C7A 1.422(7) . ? C6 C9 1.472(6) . ? C7A C8A 1.357(8) . ? C7A H7A 0.9500 . ? C8A H8A 0.9500 . ? C9 C10 1.366(6) . ? C9 C14 1.418(6) . ? C10 C11 1.405(6) . ? C10 H10 0.9500 . ? C11 C12 1.356(6) . ? C11 C16 1.479(6) . ? C12 H12 0.9500 . ? C16 C21 1.379(6) . ? C16 C17 1.381(6) . ? C17 C18 1.378(6) . ? C17 H17 0.9500 . ? C18 C19 1.367(7) . ? C18 H18 0.9500 . ? C19 C20 1.376(6) . ? C20 C21 1.380(6) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C5B H5B 0.9500 . ? C27 O28A 1.242(6) . ? C27 O26B 1.259(6) . ? C27 C29B 1.438(8) . ? C27 C29A 1.483(7) . ? C8B H8B 0.9500 . ? C29A C29A 1.363(16) 2_875 ? C29A H29A 0.9500 . ? C31 C33 1.467(7) . ? C33 C33 1.319(10) 2_676 ? C33 H33 0.9500 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C1B H1B1 0.9800 . ? C1B H1B2 0.9800 . ? C1B H1B3 0.9800 . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C29B C29B 1.35(2) 2_875 ? C29B H29B 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 O23 S22 O24 118.3(2) . . ? O23 S22 C25 109.0(2) . . ? O24 S22 C25 108.7(3) . . ? O23 S22 C19 108.1(2) . . ? O24 S22 C19 107.5(2) . . ? C25 S22 C19 104.4(2) . . ? C3 O2 C1A 115.5(5) . . ? C3 O2 C1B 117.3(7) . . ? C31 O30 H30 109.5 . . ? C35 O34 H34 109.5 . . ? C3 N4A C5A 120.5(6) . . ? C14 N13 C12 123.4(4) . . ? C14 N13 H13 118.3 . . ? C12 N13 H13 118.3 . . ? C14 N15 H15A 120.0 . . ? C14 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? C3 N4B C5B 114.0(16) . . ? N4A C3 N4B 66.8(7) . . ? N4A C3 C8B 87.6(9) . . ? N4B C3 C8B 128.8(16) . . ? N4A C3 O2 123.2(5) . . ? N4B C3 O2 115.1(10) . . ? C8B C3 O2 116.0(13) . . ? N4A C3 C8A 122.2(5) . . ? N4B C3 C8A 86.7(7) . . ? C8B C3 C8A 70.1(7) . . ? O2 C3 C8A 114.4(4) . . ? C8B C7B C6 122(2) . . ? C8B C7B H7B 118.8 . . ? C6 C7B H7B 118.8 . . ? N4A C5A C6 123.8(6) . . ? N4A C5A H5A 118.1 . . ? C6 C5A H5A 118.1 . . ? C5A C6 C7B 79.8(8) . . ? C5A C6 C5B 60.7(7) . . ? C7B C6 C5B 111.8(13) . . ? C5A C6 C7A 117.2(5) . . ? C7B C6 C7A 69.0(7) . . ? C5B C6 C7A 82.1(7) . . ? C5A C6 C9 120.9(4) . . ? C7B C6 C9 123.4(10) . . ? C5B C6 C9 124.4(9) . . ? C7A C6 C9 121.8(4) . . ? C8A C7A C6 119.6(5) . . ? C8A C7A H7A 120.2 . . ? C6 C7A H7A 120.2 . . ? C7A C8A C3 116.5(5) . . ? C7A C8A H8A 121.7 . . ? C3 C8A H8A 121.7 . . ? C10 C9 C14 117.4(4) . . ? C10 C9 C6 121.3(4) . . ? C14 C9 C6 121.1(4) . . ? C9 C10 C11 123.1(4) . . ? C9 C10 H10 118.4 . . ? C11 C10 H10 118.4 . . ? C12 C11 C10 116.3(4) . . ? C12 C11 C16 122.2(4) . . ? C10 C11 C16 121.4(4) . . ? N13 C12 C11 121.3(4) . . ? N13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? N15 C14 N13 117.4(4) . . ? N15 C14 C9 124.2(4) . . ? N13 C14 C9 118.3(4) . . ? C21 C16 C17 118.9(4) . . ? C21 C16 C11 120.3(4) . . ? C17 C16 C11 120.8(4) . . ? C18 C17 C16 120.2(4) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 120.1(4) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 120.6(4) . . ? C18 C19 S22 120.6(3) . . ? C20 C19 S22 118.8(3) . . ? C19 C20 C21 119.0(4) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C16 C21 C20 121.1(4) . . ? C16 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? S22 C25 H25A 109.5 . . ? S22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N4B C5B C6 126.6(17) . . ? N4B C5B H5B 116.7 . . ? C6 C5B H5B 116.7 . . ? O28A C27 O26B 111.9(6) . . ? O26B C27 O28B 125.4(6) . . ? O28A C27 O26A 122.1(5) . . ? O28B C27 O26A 123.1(5) . . ? O28A C27 C29B 114.2(7) . . ? O26B C27 C29B 119.1(7) . . ? O28B C27 C29B 114.6(7) . . ? O26A C27 C29B 120.6(7) . . ? O28A C27 C29A 122.1(6) . . ? O26B C27 C29A 121.3(6) . . ? O28B C27 C29A 112.9(5) . . ? O26A C27 C29A 115.7(5) . . ? C3 C8B C7B 116(2) . . ? C3 C8B H8B 121.8 . . ? C7B C8B H8B 121.8 . . ? C29A C29A C27 119.3(9) 2_875 . ? C29A C29A H29A 120.3 2_875 . ? C27 C29A H29A 120.3 . . ? O32 C31 O30 124.4(5) . . ? O32 C31 C33 121.8(5) . . ? O30 C31 C33 113.8(4) . . ? C33 C33 C31 123.1(6) 2_676 . ? C33 C33 H33 118.5 2_676 . ? C31 C33 H33 118.5 . . ? O34 C35 H35A 109.5 . . ? O34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O2 C1B H1B1 109.5 . . ? O2 C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? O2 C1B H1B3 109.5 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? O2 C1A H1A1 109.5 . . ? O2 C1A H1A2 109.5 . . ? O2 C1A H1A3 109.5 . . ? C29B C29B C27 125.6(15) 2_875 . ? C29B C29B H29B 117.2 2_875 . ? C27 C29B H29B 117.2 . . ? 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 C5A N4A C3 N4B -75.2(11) . . . . ? C5A N4A C3 C8B 59.3(12) . . . . ? C5A N4A C3 O2 179.1(5) . . . . ? C5A N4A C3 C8A -5.3(9) . . . . ? C5B N4B C3 N4A 65.9(6) . . . . ? C5B N4B C3 C8B -0.4(3) . . . . ? C5B N4B C3 O2 -176.9(6) . . . . ? C5B N4B C3 C8A -61.4(5) . . . . ? C1A O2 C3 N4A 7.3(10) . . . . ? C1B O2 C3 N4A 36.0(14) . . . . ? C1A O2 C3 N4B -70.5(10) . . . . ? C1B O2 C3 N4B -41.7(14) . . . . ? C1A O2 C3 C8B 112.6(9) . . . . ? C1B O2 C3 C8B 141.4(13) . . . . ? C1A O2 C3 C8A -168.7(8) . . . . ? C1B O2 C3 C8A -139.9(13) . . . . ? C3 N4A C5A C6 2.9(9) . . . . ? N4A C5A C6 C7B -59.1(10) . . . . ? N4A C5A C6 C5B 63.1(10) . . . . ? N4A C5A C6 C7A 0.8(8) . . . . ? N4A C5A C6 C9 177.9(5) . . . . ? C8B C7B C6 C5A 56.4(7) . . . . ? C8B C7B C6 C5B 3.8(10) . . . . ? C8B C7B C6 C7A -68.0(7) . . . . ? C8B C7B C6 C9 176.9(6) . . . . ? C5A C6 C7A C8A -2.0(8) . . . . ? C7B C6 C7A C8A 63.9(11) . . . . ? C5B C6 C7A C8A -53.2(9) . . . . ? C9 C6 C7A C8A -179.0(5) . . . . ? C6 C7A C8A C3 -0.2(8) . . . . ? N4A C3 C8A C7A 4.0(8) . . . . ? N4B C3 C8A C7A 63.8(10) . . . . ? C8B C3 C8A C7A -69.7(14) . . . . ? O2 C3 C8A C7A 179.9(5) . . . . ? C5A C6 C9 C10 -36.6(7) . . . . ? C7B C6 C9 C10 -135.1(8) . . . . ? C5B C6 C9 C10 37.1(8) . . . . ? C7A C6 C9 C10 140.3(5) . . . . ? C5A C6 C9 C14 139.5(5) . . . . ? C7B C6 C9 C14 41.0(9) . . . . ? C5B C6 C9 C14 -146.8(7) . . . . ? C7A C6 C9 C14 -43.6(7) . . . . ? C14 C9 C10 C11 0.4(7) . . . . ? C6 C9 C10 C11 176.6(4) . . . . ? C9 C10 C11 C12 -0.2(7) . . . . ? C9 C10 C11 C16 -179.0(4) . . . . ? C14 N13 C12 C11 2.1(7) . . . . ? C10 C11 C12 N13 -1.0(7) . . . . ? C16 C11 C12 N13 177.8(4) . . . . ? C12 N13 C14 N15 178.4(5) . . . . ? C12 N13 C14 C9 -1.8(7) . . . . ? C10 C9 C14 N15 -179.6(5) . . . . ? C6 C9 C14 N15 4.2(7) . . . . ? C10 C9 C14 N13 0.6(6) . . . . ? C6 C9 C14 N13 -175.6(4) . . . . ? C12 C11 C16 C21 166.4(5) . . . . ? C10 C11 C16 C21 -14.9(7) . . . . ? C12 C11 C16 C17 -14.6(7) . . . . ? C10 C11 C16 C17 164.1(5) . . . . ? C21 C16 C17 C18 2.0(8) . . . . ? C11 C16 C17 C18 -177.0(5) . . . . ? C16 C17 C18 C19 0.5(9) . . . . ? C17 C18 C19 C20 -2.3(8) . . . . ? C17 C18 C19 S22 177.0(4) . . . . ? O23 S22 C19 C18 -153.7(4) . . . . ? O24 S22 C19 C18 -25.0(5) . . . . ? C25 S22 C19 C18 90.3(5) . . . . ? O23 S22 C19 C20 25.6(5) . . . . ? O24 S22 C19 C20 154.3(4) . . . . ? C25 S22 C19 C20 -90.4(5) . . . . ? C18 C19 C20 C21 1.6(8) . . . . ? S22 C19 C20 C21 -177.7(4) . . . . ? C17 C16 C21 C20 -2.7(9) . . . . ? C11 C16 C21 C20 176.3(5) . . . . ? C19 C20 C21 C16 0.9(9) . . . . ? C3 N4B C5B C6 2.1(8) . . . . ? C5A C6 C5B N4B -67.5(8) . . . . ? C7B C6 C5B N4B -3.7(10) . . . . ? C7A C6 C5B N4B 59.9(8) . . . . ? C9 C6 C5B N4B -176.7(6) . . . . ? N4A C3 C8B C7B -56.7(6) . . . . ? N4B C3 C8B C7B 0.7(4) . . . . ? O2 C3 C8B C7B 177.1(6) . . . . ? C8A C3 C8B C7B 68.9(7) . . . . ? C6 C7B C8B C3 -2.5(8) . . . . ? O28A C27 C29A C29A 8.7(15) . . . 2_875 ? O26B C27 C29A C29A -145.1(11) . . . 2_875 ? O28B C27 C29A C29A 41.9(14) . . . 2_875 ? O26A C27 C29A C29A -168.6(10) . . . 2_875 ? C29B C27 C29A C29A -58(2) . . . 2_875 ? O32 C31 C33 C33 160.9(7) . . . 2_676 ? O30 C31 C33 C33 -18.2(10) . . . 2_676 ? O28A C27 C29B C29B -56(2) . . . 2_875 ? O26B C27 C29B C29B 168.4(19) . . . 2_875 ? O28B C27 C29B C29B -22(3) . . . 2_875 ? O26A C27 C29B C29B 143.8(19) . . . 2_875 ? C29A C27 C29B C29B 66(3) . . . 2_875 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.992 _refine_diff_density_min -0.858 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 959476' ####################################################################### # # 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_d:\dyanne\2012\struct~1\007oxa~1\oap21c _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-6(-Methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)- pyridine-2-amine.ethanedioate tetrahydrate ; _chemical_name_common '007 oxalic acid hydrate salt' _chemical_melting_point 482 _chemical_formula_moiety 'C18 H18 N3 O3 S, 0.5(C2 O4), 4(H2 O)' _chemical_formula_sum 'C19 H26 N3 O9 S' _chemical_formula_weight 472.49 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 18.581(2) _cell_length_b 5.1754(7) _cell_length_c 23.326(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.774(2) _cell_angle_gamma 90.00 _cell_volume 2147.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4051 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 25.66 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 996 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9550 _exptl_absorpt_correction_T_max 0.9823 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II Duo diffractometer' _diffrn_measurement_method 'phi-scan of 0.5 deg.' _diffrn_reflns_number 9436 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.66 _reflns_number_total 4051 _reflns_number_gt 3035 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXH-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury (Macrae at al., 2006) and POV-RAY (Cason, 2003) ; _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0608P)^2^+0.6000P] 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 4051 _refine_ls_number_parameters 327 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.054 _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 S22 S 0.52183(3) 0.07322(11) 0.37266(3) 0.02128(16) Uani 1 1 d . . . O1W O -0.01396(12) -0.8406(4) 0.33145(10) 0.0418(5) Uani 1 1 d D . . O2 O 0.31591(9) 0.9533(3) 0.77692(7) 0.0286(4) Uani 1 1 d . . . O2W O 0.13685(13) -0.4359(4) 0.37460(10) 0.0453(5) Uani 1 1 d D . . O3W O 0.08071(12) 0.3391(5) 0.69667(9) 0.0400(5) Uani 1 1 d D . . O4W O 0.13028(13) 0.4472(4) 0.82088(10) 0.0420(5) Uani 1 1 d D . . O23 O 0.53279(10) -0.1949(3) 0.36073(9) 0.0328(4) Uani 1 1 d . . . O24 O 0.58495(9) 0.2152(3) 0.40956(8) 0.0280(4) Uani 1 1 d . . . O26 O -0.00839(9) -0.7427(3) 0.44632(7) 0.0276(4) Uani 1 1 d . . . O28 O 0.06469(9) -0.3936(3) 0.46284(7) 0.0274(4) Uani 1 1 d . . . N4 N 0.34038(11) 0.6416(4) 0.71920(9) 0.0251(5) Uani 1 1 d . . . N13 N 0.16018(11) 0.0034(4) 0.50982(9) 0.0227(4) Uani 1 1 d D . . N15 N 0.10933(10) 0.1633(4) 0.58087(9) 0.0218(4) Uani 1 1 d . . . H15A H 0.0698 0.0647 0.5657 0.026 Uiso 1 1 calc R . . H15B H 0.1111 0.2633 0.6118 0.026 Uiso 1 1 calc R . . C1 C 0.26388(15) 1.1245(6) 0.79285(12) 0.0361(7) Uani 1 1 d . . . H1A H 0.2228 1.0236 0.8002 0.054 Uiso 1 1 calc R . . H1B H 0.2434 1.2463 0.7600 0.054 Uiso 1 1 calc R . . H1C H 0.2900 1.2202 0.8292 0.054 Uiso 1 1 calc R . . C3 C 0.28858(13) 0.8004(4) 0.72858(10) 0.0208(5) Uani 1 1 d . . . C5 C 0.31983(13) 0.4852(5) 0.67173(10) 0.0231(5) Uani 1 1 d . . . H5 H 0.3566 0.3707 0.6651 0.028 Uiso 1 1 calc R . . C6 C 0.24788(12) 0.4787(4) 0.63118(10) 0.0193(5) Uani 1 1 d . . . C7 C 0.19485(13) 0.6449(4) 0.64305(10) 0.0209(5) Uani 1 1 d . . . H7 H 0.1449 0.6469 0.6171 0.025 Uiso 1 1 calc R . . C8 C 0.21447(13) 0.8065(5) 0.69218(11) 0.0226(5) Uani 1 1 d . . . H8 H 0.1785 0.9185 0.7009 0.027 Uiso 1 1 calc R . . C9 C 0.23329(12) 0.3118(4) 0.57744(10) 0.0187(5) Uani 1 1 d . . . C10 C 0.28639(13) 0.2916(4) 0.54705(10) 0.0209(5) Uani 1 1 d . . . H10 H 0.3311 0.3911 0.5605 0.025 Uiso 1 1 calc R . . C11 C 0.27744(12) 0.1292(4) 0.49665(10) 0.0207(5) Uani 1 1 d . . . C12 C 0.21312(13) -0.0147(5) 0.48010(10) 0.0228(5) Uani 1 1 d . . . H12 H 0.2052 -0.1298 0.4471 0.027 Uiso 1 1 calc R . . C14 C 0.16642(12) 0.1612(4) 0.55718(10) 0.0186(5) Uani 1 1 d . . . C16 C 0.33573(12) 0.1152(4) 0.46447(10) 0.0205(5) Uani 1 1 d . . . C17 C 0.33715(14) -0.0825(5) 0.42452(12) 0.0314(6) Uani 1 1 d . . . H17 H 0.2991 -0.2112 0.4167 0.038 Uiso 1 1 calc R . . C18 C 0.39274(14) -0.0967(5) 0.39579(12) 0.0309(6) Uani 1 1 d . . . H18 H 0.3927 -0.2337 0.3687 0.037 Uiso 1 1 calc R . . C19 C 0.44827(13) 0.0896(4) 0.40689(10) 0.0217(5) Uani 1 1 d . . . C20 C 0.44664(15) 0.2907(6) 0.44477(13) 0.0385(7) Uani 1 1 d . . . H20 H 0.4838 0.4221 0.4514 0.046 Uiso 1 1 calc R . . C21 C 0.39082(15) 0.3031(6) 0.47356(13) 0.0376(7) Uani 1 1 d . . . H21 H 0.3905 0.4429 0.4999 0.045 Uiso 1 1 calc R . . C25 C 0.48682(14) 0.2338(5) 0.30411(11) 0.0252(5) Uani 1 1 d . . . H25A H 0.4416 0.1450 0.2800 0.038 Uiso 1 1 calc R . . H25B H 0.5250 0.2337 0.2826 0.038 Uiso 1 1 calc R . . H25C H 0.4742 0.4123 0.3114 0.038 Uiso 1 1 calc R . . C27 C 0.01619(12) -0.5392(4) 0.47376(10) 0.0210(5) Uani 1 1 d . . . H13 H 0.1216(10) -0.102(4) 0.4975(12) 0.037(8) Uiso 1 1 d D . . H3 H 0.1078(16) -0.431(8) 0.3952(14) 0.076(13) Uiso 1 1 d D . . H6 H 0.0554(19) 0.208(4) 0.6948(18) 0.077(13) Uiso 1 1 d D . . H9 H 0.0494(17) 0.454(5) 0.6850(17) 0.081(15) Uiso 1 1 d D . . H2 H -0.002(2) -0.809(8) 0.3674(4) 0.088(15) Uiso 1 1 d D . . H11 H 0.119(2) 0.444(8) 0.78419(13) 0.075(13) Uiso 1 1 d D . . H4 H 0.140(3) -0.586(3) 0.364(2) 0.104(17) Uiso 1 1 d D . . H14 H 0.122(4) 0.603(3) 0.822(4) 0.21(4) Uiso 1 1 d D . . H1 H 0.0291(8) -0.858(8) 0.3294(17) 0.071(13) Uiso 1 1 d 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 S22 0.0189(3) 0.0206(3) 0.0259(3) -0.0018(2) 0.0090(2) 0.0003(2) O1W 0.0386(12) 0.0509(13) 0.0382(13) -0.0062(10) 0.0149(10) -0.0050(10) O2 0.0269(9) 0.0321(10) 0.0253(9) -0.0093(8) 0.0054(7) 0.0012(8) O2W 0.0641(14) 0.0367(13) 0.0481(13) -0.0102(10) 0.0368(12) -0.0130(11) O3W 0.0405(12) 0.0422(13) 0.0395(12) 0.0003(10) 0.0151(10) -0.0016(11) O4W 0.0511(13) 0.0440(13) 0.0358(12) 0.0046(10) 0.0200(10) 0.0040(10) O23 0.0307(10) 0.0203(9) 0.0529(12) -0.0044(8) 0.0209(9) 0.0023(7) O24 0.0195(8) 0.0336(10) 0.0298(9) -0.0021(8) 0.0054(7) -0.0047(7) O26 0.0276(9) 0.0264(10) 0.0300(10) -0.0080(7) 0.0099(8) -0.0079(7) O28 0.0268(9) 0.0276(9) 0.0327(10) -0.0062(7) 0.0162(8) -0.0104(8) N4 0.0193(10) 0.0321(12) 0.0241(11) -0.0038(9) 0.0068(8) 0.0014(9) N13 0.0172(10) 0.0253(11) 0.0243(11) -0.0030(9) 0.0039(8) -0.0045(8) N15 0.0172(10) 0.0235(10) 0.0260(11) -0.0033(8) 0.0083(8) -0.0047(8) C1 0.0369(15) 0.0375(16) 0.0362(16) -0.0151(12) 0.0139(13) 0.0023(12) C3 0.0234(12) 0.0209(12) 0.0189(12) -0.0012(10) 0.0073(10) -0.0011(10) C5 0.0178(11) 0.0272(13) 0.0252(13) -0.0038(10) 0.0075(10) 0.0028(10) C6 0.0193(11) 0.0183(11) 0.0214(12) 0.0010(9) 0.0076(9) -0.0026(9) C7 0.0165(11) 0.0210(12) 0.0231(12) 0.0003(10) 0.0025(9) -0.0020(9) C8 0.0193(12) 0.0218(12) 0.0280(13) -0.0006(10) 0.0087(10) 0.0033(10) C9 0.0176(11) 0.0184(11) 0.0193(12) 0.0005(9) 0.0041(9) 0.0002(9) C10 0.0178(11) 0.0225(12) 0.0213(12) 0.0002(10) 0.0040(9) -0.0013(9) C11 0.0201(12) 0.0208(12) 0.0217(12) 0.0003(10) 0.0067(10) -0.0010(9) C12 0.0214(12) 0.0258(13) 0.0220(12) -0.0040(10) 0.0075(10) -0.0017(10) C14 0.0168(11) 0.0162(11) 0.0209(12) 0.0030(9) 0.0026(9) 0.0004(9) C16 0.0195(11) 0.0218(12) 0.0197(12) 0.0007(9) 0.0048(9) 0.0001(9) C17 0.0301(13) 0.0305(14) 0.0382(15) -0.0118(12) 0.0173(12) -0.0135(11) C18 0.0328(14) 0.0293(14) 0.0350(14) -0.0129(11) 0.0170(12) -0.0083(11) C19 0.0212(12) 0.0239(12) 0.0214(12) 0.0008(10) 0.0082(10) 0.0006(10) C20 0.0342(15) 0.0404(16) 0.0482(17) -0.0222(14) 0.0234(13) -0.0189(13) C21 0.0372(15) 0.0414(16) 0.0411(16) -0.0225(13) 0.0226(13) -0.0182(13) C25 0.0242(12) 0.0273(13) 0.0251(13) -0.0015(10) 0.0086(10) -0.0032(10) C27 0.0151(11) 0.0236(13) 0.0226(12) 0.0004(10) 0.0026(9) -0.0004(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 S22 O24 1.4400(17) . ? S22 O23 1.4413(18) . ? S22 C25 1.752(2) . ? S22 C19 1.773(2) . ? O1W H2 0.8202(11) . ? O1W H1 0.8202(11) . ? O2 C3 1.351(3) . ? O2 C1 1.437(3) . ? O2W H3 0.8202(10) . ? O2W H4 0.8201(11) . ? O3W H6 0.8201(11) . ? O3W H9 0.8201(11) . ? O4W H11 0.8201(11) . ? O4W H14 0.8201(12) . ? O26 C27 1.248(3) . ? O28 C27 1.256(3) . ? N4 C3 1.331(3) . ? N4 C5 1.335(3) . ? N13 C14 1.352(3) . ? N13 C12 1.360(3) . ? N13 H13 0.8800(11) . ? N15 C14 1.330(3) . ? N15 H15A 0.8800 . ? N15 H15B 0.8800 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3 C8 1.394(3) . ? C5 C6 1.398(3) . ? C5 H5 0.9500 . ? C6 C7 1.395(3) . ? C6 C9 1.481(3) . ? C7 C8 1.380(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.375(3) . ? C9 C14 1.427(3) . ? C10 C11 1.415(3) . ? C10 H10 0.9500 . ? C11 C12 1.366(3) . ? C11 C16 1.487(3) . ? C12 H12 0.9500 . ? C16 C21 1.383(3) . ? C16 C17 1.390(3) . ? C17 C18 1.386(3) . ? C17 H17 0.9500 . ? C18 C19 1.381(3) . ? C18 H18 0.9500 . ? C19 C20 1.371(3) . ? C20 C21 1.390(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C27 C27 1.565(5) 3_546 ? 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 O24 S22 O23 118.06(11) . . ? O24 S22 C25 109.11(11) . . ? O23 S22 C25 108.45(12) . . ? O24 S22 C19 107.89(11) . . ? O23 S22 C19 107.66(11) . . ? C25 S22 C19 104.89(11) . . ? H2 O1W H1 95(4) . . ? C3 O2 C1 117.26(19) . . ? H3 O2W H4 108(4) . . ? H6 O3W H9 104(4) . . ? H11 O4W H14 93(6) . . ? C3 N4 C5 117.6(2) . . ? C14 N13 C12 123.6(2) . . ? C14 N13 H13 120.7(19) . . ? C12 N13 H13 115.6(19) . . ? C14 N15 H15A 120.0 . . ? C14 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N4 C3 O2 112.5(2) . . ? N4 C3 C8 123.2(2) . . ? O2 C3 C8 124.2(2) . . ? N4 C5 C6 124.4(2) . . ? N4 C5 H5 117.8 . . ? C6 C5 H5 117.8 . . ? C7 C6 C5 116.3(2) . . ? C7 C6 C9 124.1(2) . . ? C5 C6 C9 119.5(2) . . ? C8 C7 C6 120.4(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C3 118.0(2) . . ? C7 C8 H8 121.0 . . ? C3 C8 H8 121.0 . . ? C10 C9 C14 118.3(2) . . ? C10 C9 C6 119.8(2) . . ? C14 C9 C6 121.9(2) . . ? C9 C10 C11 122.9(2) . . ? C9 C10 H10 118.5 . . ? C11 C10 H10 118.5 . . ? C12 C11 C10 116.2(2) . . ? C12 C11 C16 122.4(2) . . ? C10 C11 C16 121.3(2) . . ? N13 C12 C11 121.4(2) . . ? N13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? N15 C14 N13 117.0(2) . . ? N15 C14 C9 125.5(2) . . ? N13 C14 C9 117.5(2) . . ? C21 C16 C17 117.7(2) . . ? C21 C16 C11 120.2(2) . . ? C17 C16 C11 122.1(2) . . ? C18 C17 C16 121.6(2) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C19 C18 C17 119.5(2) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C20 C19 C18 119.8(2) . . ? C20 C19 S22 119.32(18) . . ? C18 C19 S22 120.90(18) . . ? C19 C20 C21 120.3(2) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C16 C21 C20 121.0(2) . . ? C16 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? S22 C25 H25A 109.5 . . ? S22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O26 C27 O28 125.4(2) . . ? O26 C27 C27 117.0(2) . 3_546 ? O28 C27 C27 117.6(3) . 3_546 ? 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 C5 N4 C3 O2 -178.6(2) . . . . ? C5 N4 C3 C8 1.3(4) . . . . ? C1 O2 C3 N4 -177.2(2) . . . . ? C1 O2 C3 C8 2.8(3) . . . . ? C3 N4 C5 C6 0.5(4) . . . . ? N4 C5 C6 C7 -1.5(4) . . . . ? N4 C5 C6 C9 175.1(2) . . . . ? C5 C6 C7 C8 0.7(3) . . . . ? C9 C6 C7 C8 -175.7(2) . . . . ? C6 C7 C8 C3 0.9(3) . . . . ? N4 C3 C8 C7 -2.0(4) . . . . ? O2 C3 C8 C7 177.9(2) . . . . ? C7 C6 C9 C10 136.8(2) . . . . ? C5 C6 C9 C10 -39.5(3) . . . . ? C7 C6 C9 C14 -45.8(3) . . . . ? C5 C6 C9 C14 138.0(2) . . . . ? C14 C9 C10 C11 0.2(3) . . . . ? C6 C9 C10 C11 177.8(2) . . . . ? C9 C10 C11 C12 -1.6(3) . . . . ? C9 C10 C11 C16 179.2(2) . . . . ? C14 N13 C12 C11 0.0(4) . . . . ? C10 C11 C12 N13 1.6(3) . . . . ? C16 C11 C12 N13 -179.3(2) . . . . ? C12 N13 C14 N15 178.4(2) . . . . ? C12 N13 C14 C9 -1.4(3) . . . . ? C10 C9 C14 N15 -178.5(2) . . . . ? C6 C9 C14 N15 4.0(4) . . . . ? C10 C9 C14 N13 1.3(3) . . . . ? C6 C9 C14 N13 -176.2(2) . . . . ? C12 C11 C16 C21 165.2(2) . . . . ? C10 C11 C16 C21 -15.6(3) . . . . ? C12 C11 C16 C17 -14.5(4) . . . . ? C10 C11 C16 C17 164.6(2) . . . . ? C21 C16 C17 C18 1.7(4) . . . . ? C11 C16 C17 C18 -178.5(2) . . . . ? C16 C17 C18 C19 0.0(4) . . . . ? C17 C18 C19 C20 -1.9(4) . . . . ? C17 C18 C19 S22 178.2(2) . . . . ? O24 S22 C19 C20 24.1(2) . . . . ? O23 S22 C19 C20 152.5(2) . . . . ? C25 S22 C19 C20 -92.1(2) . . . . ? O24 S22 C19 C18 -156.0(2) . . . . ? O23 S22 C19 C18 -27.6(2) . . . . ? C25 S22 C19 C18 87.8(2) . . . . ? C18 C19 C20 C21 2.1(4) . . . . ? S22 C19 C20 C21 -178.0(2) . . . . ? C17 C16 C21 C20 -1.5(4) . . . . ? C11 C16 C21 C20 178.7(3) . . . . ? C19 C20 C21 C16 -0.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.388 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 959477' ####################################################################### # # 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_c:\dyanne~1\2013\007\s2sacc~1\c2c _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-6(-Methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)- pyridine-2-amine. 2H-1lamda6,2-benzothiazol-1,1,3-trione salt hydrate ; _chemical_name_common ? _chemical_melting_point 477 _chemical_formula_moiety 'C18 H18 N3 O3 S1, C7 H3 N1 O3 S1, 2.48(H2 O1)' _chemical_formula_sum 'C25 H26.97 N4 O8.48 S2' _chemical_formula_weight 583.34 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 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.4221(6) _cell_length_b 16.7460(8) _cell_length_c 25.6251(12) _cell_angle_alpha 90.00 _cell_angle_beta 99.4440(10) _cell_angle_gamma 90.00 _cell_volume 5681.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7072 _cell_measurement_theta_min 1.96 _cell_measurement_theta_max 28.33 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2439 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9096 _exptl_absorpt_correction_T_max 0.9752 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II Duo diffractometer' _diffrn_measurement_method 'phi- and omega-scans of 0.5 deg.' _diffrn_reflns_number 51740 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.33 _reflns_number_total 7072 _reflns_number_gt 5869 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXH-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury (Macrae at al., 2006) and POV-RAY (Cason, 2003) ; _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0683P)^2^+10.2423P] 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 7072 _refine_ls_number_parameters 368 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1440 _refine_ls_wR_factor_gt 0.1365 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 S22 S 0.63024(4) 0.08219(3) 0.38372(2) 0.02795(13) Uani 1 1 d . . . S34 S 0.75475(4) 0.10943(3) 0.57717(2) 0.02756(13) Uani 1 1 d . . . O2 O 0.04422(13) -0.06707(11) 0.68693(6) 0.0391(4) Uani 1 1 d . . . O23 O 0.61544(14) 0.09851(12) 0.32775(6) 0.0445(4) Uani 1 1 d . . . O24 O 0.66090(12) 0.00266(9) 0.40128(7) 0.0377(4) Uani 1 1 d . . . O35 O 0.84176(12) 0.16134(10) 0.58799(7) 0.0373(4) Uani 1 1 d . . . O36 O 0.75491(14) 0.05594(11) 0.53315(7) 0.0435(4) Uani 1 1 d . . . O37 O 0.51224(12) 0.17068(10) 0.61077(7) 0.0395(4) Uani 1 1 d . . . N4 N 0.06870(14) -0.05234(11) 0.60034(7) 0.0307(4) Uani 1 1 d . . . N13 N 0.08498(12) 0.22528(10) 0.45470(7) 0.0256(3) Uani 1 1 d . . . H13 H 0.0452 0.2623 0.4382 0.031 Uiso 1 1 calc R . . N15 N -0.03662(13) 0.20554(11) 0.50705(7) 0.0297(4) Uani 1 1 d . . . H15A H -0.0736 0.2424 0.4886 0.036 Uiso 1 1 calc R . . H15B H -0.0592 0.1813 0.5333 0.036 Uiso 1 1 calc R . . N33 N 0.65091(13) 0.16074(10) 0.57002(7) 0.0274(4) Uani 1 1 d . . . C1 C 0.0405(3) -0.15166(17) 0.67803(12) 0.0545(7) Uani 1 1 d . . . H1A H -0.0207 -0.1651 0.6531 0.082 Uiso 1 1 calc R . . H1B H 0.0396 -0.1794 0.7116 0.082 Uiso 1 1 calc R . . H1C H 0.1001 -0.1683 0.6632 0.082 Uiso 1 1 calc R . . C3 C 0.05917(15) -0.01966(13) 0.64596(8) 0.0293(4) Uani 1 1 d . . . C5 C 0.08565(16) -0.00288(12) 0.56155(8) 0.0283(4) Uani 1 1 d . . . H5 H 0.0943 -0.0258 0.5287 0.034 Uiso 1 1 calc R . . C6 C 0.09143(14) 0.07943(12) 0.56627(8) 0.0240(4) Uani 1 1 d . . . C7 C 0.07816(18) 0.11214(14) 0.61493(9) 0.0353(5) Uani 1 1 d . . . H7 H 0.0799 0.1684 0.6200 0.042 Uiso 1 1 calc R . . C8 C 0.0625(2) 0.06206(15) 0.65534(9) 0.0393(5) Uani 1 1 d . . . H8 H 0.0542 0.0828 0.6889 0.047 Uiso 1 1 calc R . . C9 C 0.11939(14) 0.12727(11) 0.52205(8) 0.0234(4) Uani 1 1 d . . . C10 C 0.20927(14) 0.11231(11) 0.50464(8) 0.0239(4) Uani 1 1 d . . . H10 H 0.2530 0.0726 0.5222 0.029 Uiso 1 1 calc R . . C11 C 0.23934(14) 0.15370(11) 0.46156(8) 0.0229(4) Uani 1 1 d . . . C12 C 0.17397(14) 0.21059(11) 0.43791(8) 0.0248(4) Uani 1 1 d . . . H12 H 0.1912 0.2404 0.4091 0.030 Uiso 1 1 calc R . . C14 C 0.05387(14) 0.18632(11) 0.49528(8) 0.0237(4) Uani 1 1 d . . . C16 C 0.33607(14) 0.13712(11) 0.44281(8) 0.0228(4) Uani 1 1 d . . . C17 C 0.41704(14) 0.10209(12) 0.47648(8) 0.0241(4) Uani 1 1 d . . . H17 H 0.4104 0.0896 0.5119 0.029 Uiso 1 1 calc R . . C18 C 0.50712(14) 0.08539(12) 0.45849(8) 0.0245(4) Uani 1 1 d . . . H18 H 0.5615 0.0609 0.4813 0.029 Uiso 1 1 calc R . . C19 C 0.51673(14) 0.10497(11) 0.40687(8) 0.0240(4) Uani 1 1 d . . . C20 C 0.43806(16) 0.14086(13) 0.37315(8) 0.0286(4) Uani 1 1 d . . . H20 H 0.4457 0.1546 0.3381 0.034 Uiso 1 1 calc R . . C21 C 0.34798(15) 0.15652(13) 0.39122(8) 0.0281(4) Uani 1 1 d . . . H21 H 0.2937 0.1808 0.3682 0.034 Uiso 1 1 calc R . . C25 C 0.71794(16) 0.15041(14) 0.41602(10) 0.0358(5) Uani 1 1 d . . . H25A H 0.7836 0.1417 0.4049 0.054 Uiso 1 1 calc R . . H25B H 0.7246 0.1428 0.4544 0.054 Uiso 1 1 calc R . . H25C H 0.6948 0.2049 0.4069 0.054 Uiso 1 1 calc R . . C26 C 0.73726(15) 0.05718(12) 0.63481(8) 0.0282(4) Uani 1 1 d . . . C27 C 0.79881(18) 0.00340(14) 0.66564(11) 0.0412(6) Uani 1 1 d . . . H27 H 0.8619 -0.0127 0.6569 0.049 Uiso 1 1 calc R . . C28 C 0.7641(2) -0.02604(16) 0.71004(11) 0.0500(7) Uani 1 1 d . . . H28 H 0.8050 -0.0623 0.7327 0.060 Uiso 1 1 calc R . . C29 C 0.6713(2) -0.00360(18) 0.72189(10) 0.0518(7) Uani 1 1 d . . . H29 H 0.6492 -0.0251 0.7524 0.062 Uiso 1 1 calc R . . C30 C 0.6099(2) 0.04974(16) 0.69004(10) 0.0424(6) Uani 1 1 d . . . H30 H 0.5457 0.0646 0.6978 0.051 Uiso 1 1 calc R . . C31 C 0.64537(15) 0.08063(12) 0.64652(8) 0.0280(4) Uani 1 1 d . . . C32 C 0.59688(15) 0.14140(12) 0.60753(8) 0.0274(4) Uani 1 1 d . . . O1W O 0.1578(3) 0.3573(3) 0.34048(18) 0.0522(10) Uiso 0.45 1 d P A 1 O3W O 0.1839(4) 0.2439(4) 0.3024(2) 0.0508(13) Uiso 0.36 1 d P B 3 O4W O 0.3294(6) 0.2187(5) 0.2387(3) 0.0930(19) Uiso 0.46 1 d P C 1 O2W O 0.1505(8) 0.3232(6) 0.2987(4) 0.046(2) Uiso 0.19 1 d P D 2 O6W O 0.3742(9) 0.2869(7) 0.2231(5) 0.091(3) Uiso 0.26 1 d P E 2 O7W O 0.2855(9) 0.2606(8) 0.2389(5) 0.092(3) Uiso 0.28 1 d P F 5 O5W O 0.2109(6) 0.2380(4) 0.2796(3) 0.0508(16) Uiso 0.28 1 d P G 4 O8W O 0.2771(14) 0.2573(11) 0.2855(7) 0.100(5) Uiso 0.20 1 d P H 6 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 S22 0.0274(2) 0.0285(3) 0.0305(3) 0.00053(19) 0.01215(19) 0.00686(19) S34 0.0270(2) 0.0242(2) 0.0333(3) 0.00448(19) 0.01019(19) 0.00426(18) O2 0.0442(9) 0.0455(10) 0.0282(8) 0.0107(7) 0.0076(7) 0.0002(7) O23 0.0451(10) 0.0612(12) 0.0309(8) 0.0016(8) 0.0176(7) 0.0146(8) O24 0.0351(8) 0.0276(8) 0.0526(10) 0.0002(7) 0.0142(7) 0.0090(6) O35 0.0277(8) 0.0316(8) 0.0550(10) 0.0082(7) 0.0141(7) 0.0002(6) O36 0.0550(11) 0.0363(9) 0.0433(9) -0.0046(7) 0.0202(8) 0.0056(8) O37 0.0305(8) 0.0405(9) 0.0503(10) 0.0170(7) 0.0149(7) 0.0130(7) N4 0.0327(9) 0.0297(9) 0.0310(9) 0.0053(7) 0.0091(7) 0.0025(7) N13 0.0210(7) 0.0223(8) 0.0339(9) 0.0045(6) 0.0057(6) 0.0063(6) N15 0.0232(8) 0.0289(9) 0.0390(10) 0.0073(7) 0.0110(7) 0.0076(7) N33 0.0276(8) 0.0267(8) 0.0282(8) 0.0084(7) 0.0057(6) 0.0048(7) C1 0.073(2) 0.0450(15) 0.0474(15) 0.0190(12) 0.0156(14) -0.0037(14) C3 0.0225(9) 0.0370(11) 0.0284(10) 0.0080(8) 0.0040(7) 0.0028(8) C5 0.0313(10) 0.0269(10) 0.0285(10) 0.0009(8) 0.0098(8) 0.0029(8) C6 0.0186(8) 0.0264(9) 0.0275(9) 0.0026(7) 0.0054(7) 0.0038(7) C7 0.0446(12) 0.0294(11) 0.0334(11) -0.0037(9) 0.0106(9) 0.0005(9) C8 0.0513(14) 0.0423(13) 0.0257(10) -0.0027(9) 0.0107(9) 0.0010(11) C9 0.0227(9) 0.0205(8) 0.0276(9) 0.0002(7) 0.0055(7) 0.0013(7) C10 0.0229(9) 0.0209(8) 0.0279(9) 0.0003(7) 0.0046(7) 0.0038(7) C11 0.0209(8) 0.0212(9) 0.0267(9) 0.0000(7) 0.0045(7) 0.0018(7) C12 0.0221(9) 0.0230(9) 0.0302(10) 0.0034(7) 0.0070(7) 0.0017(7) C14 0.0206(8) 0.0207(8) 0.0302(9) -0.0009(7) 0.0057(7) 0.0010(7) C16 0.0217(8) 0.0203(8) 0.0272(9) -0.0003(7) 0.0067(7) 0.0022(7) C17 0.0237(9) 0.0247(9) 0.0250(9) 0.0022(7) 0.0070(7) 0.0029(7) C18 0.0225(9) 0.0252(9) 0.0260(9) 0.0016(7) 0.0048(7) 0.0034(7) C19 0.0234(9) 0.0228(9) 0.0272(9) -0.0004(7) 0.0084(7) 0.0027(7) C20 0.0299(10) 0.0314(10) 0.0256(9) 0.0045(8) 0.0078(8) 0.0066(8) C21 0.0254(9) 0.0310(10) 0.0284(10) 0.0047(8) 0.0052(7) 0.0069(8) C25 0.0267(10) 0.0304(11) 0.0525(14) 0.0020(10) 0.0132(9) 0.0010(8) C26 0.0267(9) 0.0244(9) 0.0323(10) 0.0070(8) 0.0012(8) -0.0002(8) C27 0.0304(11) 0.0328(11) 0.0565(15) 0.0129(10) -0.0047(10) 0.0033(9) C28 0.0538(15) 0.0421(14) 0.0469(14) 0.0202(12) -0.0135(12) 0.0009(12) C29 0.0687(18) 0.0514(16) 0.0346(13) 0.0210(11) 0.0058(12) -0.0048(14) C30 0.0459(13) 0.0453(14) 0.0379(12) 0.0141(10) 0.0128(10) 0.0008(11) C31 0.0280(10) 0.0277(10) 0.0279(10) 0.0073(8) 0.0032(7) 0.0013(8) C32 0.0260(9) 0.0261(9) 0.0299(10) 0.0066(8) 0.0038(7) 0.0032(7) _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 S22 O23 1.4415(17) . ? S22 O24 1.4438(16) . ? S22 C25 1.748(2) . ? S22 C19 1.7650(19) . ? S34 O36 1.4407(17) . ? S34 O35 1.4457(17) . ? S34 N33 1.6218(17) . ? S34 C26 1.765(2) . ? O2 C3 1.357(2) . ? O2 C1 1.434(3) . ? O37 C32 1.252(2) . ? N4 C3 1.316(3) . ? N4 C5 1.342(3) . ? N13 C14 1.351(3) . ? N13 C12 1.357(2) . ? N13 H13 0.8800 . ? N15 C14 1.338(2) . ? N15 H15A 0.8800 . ? N15 H15B 0.8800 . ? N33 C32 1.336(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3 C8 1.389(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.400(3) . ? C6 C9 1.485(3) . ? C7 C8 1.375(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.376(3) . ? C9 C14 1.423(3) . ? C10 C11 1.417(3) . ? C10 H10 0.9500 . ? C11 C12 1.368(3) . ? C11 C16 1.483(3) . ? C12 H12 0.9500 . ? C16 C21 1.396(3) . ? C16 C17 1.401(3) . ? C17 C18 1.391(3) . ? C17 H17 0.9500 . ? C18 C19 1.389(3) . ? C18 H18 0.9500 . ? C19 C20 1.387(3) . ? C20 C21 1.389(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C31 1.374(3) . ? C26 C27 1.380(3) . ? C27 C28 1.389(4) . ? C27 H27 0.9500 . ? C28 C29 1.382(4) . ? C28 H28 0.9500 . ? C29 C30 1.387(4) . ? C29 H29 0.9500 . ? C30 C31 1.382(3) . ? C30 H30 0.9500 . ? C31 C32 1.498(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 O23 S22 O24 118.08(11) . . ? O23 S22 C25 108.62(12) . . ? O24 S22 C25 108.66(11) . . ? O23 S22 C19 107.92(10) . . ? O24 S22 C19 108.20(9) . . ? C25 S22 C19 104.53(10) . . ? O36 S34 O35 114.78(11) . . ? O36 S34 N33 110.65(10) . . ? O35 S34 N33 110.81(9) . . ? O36 S34 C26 111.37(11) . . ? O35 S34 C26 110.59(10) . . ? N33 S34 C26 97.32(9) . . ? C3 O2 C1 117.42(19) . . ? C3 N4 C5 117.03(19) . . ? C14 N13 C12 123.78(16) . . ? C14 N13 H13 118.1 . . ? C12 N13 H13 118.1 . . ? C14 N15 H15A 120.0 . . ? C14 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? C32 N33 S34 110.38(14) . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N4 C3 O2 119.5(2) . . ? N4 C3 C8 123.9(2) . . ? O2 C3 C8 116.6(2) . . ? N4 C5 C6 124.32(19) . . ? N4 C5 H5 117.8 . . ? C6 C5 H5 117.8 . . ? C5 C6 C7 116.99(19) . . ? C5 C6 C9 119.20(18) . . ? C7 C6 C9 123.60(18) . . ? C8 C7 C6 119.3(2) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C3 118.4(2) . . ? C7 C8 H8 120.8 . . ? C3 C8 H8 120.8 . . ? C10 C9 C14 118.42(18) . . ? C10 C9 C6 119.58(17) . . ? C14 C9 C6 121.94(17) . . ? C9 C10 C11 122.70(17) . . ? C9 C10 H10 118.6 . . ? C11 C10 H10 118.6 . . ? C12 C11 C10 116.23(17) . . ? C12 C11 C16 121.27(17) . . ? C10 C11 C16 122.50(17) . . ? N13 C12 C11 121.34(18) . . ? N13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? N15 C14 N13 117.66(17) . . ? N15 C14 C9 124.81(18) . . ? N13 C14 C9 117.53(17) . . ? C21 C16 C17 118.88(17) . . ? C21 C16 C11 120.38(17) . . ? C17 C16 C11 120.73(17) . . ? C18 C17 C16 120.58(18) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C19 C18 C17 119.31(18) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C20 C19 C18 121.02(17) . . ? C20 C19 S22 119.69(15) . . ? C18 C19 S22 119.28(14) . . ? C19 C20 C21 119.32(18) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C20 C21 C16 120.87(18) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? S22 C25 H25A 109.5 . . ? S22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C31 C26 C27 122.4(2) . . ? C31 C26 S34 106.77(14) . . ? C27 C26 S34 130.79(18) . . ? C26 C27 C28 116.8(2) . . ? C26 C27 H27 121.6 . . ? C28 C27 H27 121.6 . . ? C29 C28 C27 121.3(2) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? C28 C29 C30 121.1(2) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? C31 C30 C29 117.8(2) . . ? C31 C30 H30 121.1 . . ? C29 C30 H30 121.1 . . ? C26 C31 C30 120.6(2) . . ? C26 C31 C32 110.85(18) . . ? C30 C31 C32 128.5(2) . . ? O37 C32 N33 123.93(18) . . ? O37 C32 C31 121.42(18) . . ? N33 C32 C31 114.64(17) . . ? 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 O36 S34 N33 C32 114.28(16) . . . . ? O35 S34 N33 C32 -117.23(16) . . . . ? C26 S34 N33 C32 -1.88(17) . . . . ? C5 N4 C3 O2 -178.51(18) . . . . ? C5 N4 C3 C8 2.1(3) . . . . ? C1 O2 C3 N4 0.6(3) . . . . ? C1 O2 C3 C8 180.0(2) . . . . ? C3 N4 C5 C6 -1.5(3) . . . . ? N4 C5 C6 C7 -0.2(3) . . . . ? N4 C5 C6 C9 174.73(18) . . . . ? C5 C6 C7 C8 1.4(3) . . . . ? C9 C6 C7 C8 -173.4(2) . . . . ? C6 C7 C8 C3 -0.8(4) . . . . ? N4 C3 C8 C7 -1.0(4) . . . . ? O2 C3 C8 C7 179.6(2) . . . . ? C5 C6 C9 C10 -57.2(3) . . . . ? C7 C6 C9 C10 117.4(2) . . . . ? C5 C6 C9 C14 120.0(2) . . . . ? C7 C6 C9 C14 -65.4(3) . . . . ? C14 C9 C10 C11 0.5(3) . . . . ? C6 C9 C10 C11 177.85(18) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? C9 C10 C11 C16 -179.74(18) . . . . ? C14 N13 C12 C11 0.2(3) . . . . ? C10 C11 C12 N13 -0.8(3) . . . . ? C16 C11 C12 N13 179.35(18) . . . . ? C12 N13 C14 N15 -178.63(19) . . . . ? C12 N13 C14 C9 0.8(3) . . . . ? C10 C9 C14 N15 178.25(19) . . . . ? C6 C9 C14 N15 1.0(3) . . . . ? C10 C9 C14 N13 -1.1(3) . . . . ? C6 C9 C14 N13 -178.36(18) . . . . ? C12 C11 C16 C21 -22.8(3) . . . . ? C10 C11 C16 C21 157.35(19) . . . . ? C12 C11 C16 C17 156.95(19) . . . . ? C10 C11 C16 C17 -22.9(3) . . . . ? C21 C16 C17 C18 -1.3(3) . . . . ? C11 C16 C17 C18 178.92(18) . . . . ? C16 C17 C18 C19 1.0(3) . . . . ? C17 C18 C19 C20 0.0(3) . . . . ? C17 C18 C19 S22 -178.90(15) . . . . ? O23 S22 C19 C20 -6.6(2) . . . . ? O24 S22 C19 C20 -135.45(17) . . . . ? C25 S22 C19 C20 108.88(19) . . . . ? O23 S22 C19 C18 172.35(17) . . . . ? O24 S22 C19 C18 43.51(19) . . . . ? C25 S22 C19 C18 -72.15(18) . . . . ? C18 C19 C20 C21 -0.8(3) . . . . ? S22 C19 C20 C21 178.18(16) . . . . ? C19 C20 C21 C16 0.4(3) . . . . ? C17 C16 C21 C20 0.6(3) . . . . ? C11 C16 C21 C20 -179.64(19) . . . . ? O36 S34 C26 C31 -113.84(17) . . . . ? O35 S34 C26 C31 117.28(16) . . . . ? N33 S34 C26 C31 1.75(17) . . . . ? O36 S34 C26 C27 67.2(2) . . . . ? O35 S34 C26 C27 -61.7(2) . . . . ? N33 S34 C26 C27 -177.2(2) . . . . ? C31 C26 C27 C28 -0.6(4) . . . . ? S34 C26 C27 C28 178.2(2) . . . . ? C26 C27 C28 C29 1.4(4) . . . . ? C27 C28 C29 C30 -0.6(5) . . . . ? C28 C29 C30 C31 -1.0(4) . . . . ? C27 C26 C31 C30 -0.9(4) . . . . ? S34 C26 C31 C30 179.99(19) . . . . ? C27 C26 C31 C32 178.0(2) . . . . ? S34 C26 C31 C32 -1.1(2) . . . . ? C29 C30 C31 C26 1.7(4) . . . . ? C29 C30 C31 C32 -177.0(2) . . . . ? S34 N33 C32 O37 -178.40(19) . . . . ? S34 N33 C32 C31 1.5(2) . . . . ? C26 C31 C32 O37 179.7(2) . . . . ? C30 C31 C32 O37 -1.5(4) . . . . ? C26 C31 C32 N33 -0.2(3) . . . . ? C30 C31 C32 N33 178.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.887 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 959478' ####################################################################### # # 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_c:\dyanne~1\2013\007\s1sali~1\p21c _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-6(-Methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)- pyridine-2-amine. 2-hydroxybenzoate salt hydrate ; _chemical_name_common ? _chemical_melting_point 452 _chemical_formula_moiety 'C18 H18 N3 O3 S, C7 H5 O3 S, H2 O1' _chemical_formula_sum 'C25 H25 N3 O7 S' _chemical_formula_weight 511.54 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 13.2320(8) _cell_length_b 11.6031(7) _cell_length_c 16.5449(10) _cell_angle_alpha 90.00 _cell_angle_beta 110.9770(10) _cell_angle_gamma 90.00 _cell_volume 2371.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7246 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 30.58 _exptl_crystal_description blocks _exptl_crystal_colour 'translucent yellow' _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8972 _exptl_absorpt_correction_T_max 0.9585 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II Duo diffractometer' _diffrn_measurement_method 'phi- and omega-scans of 0.5 deg.' _diffrn_reflns_number 44253 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 30.58 _reflns_number_total 7246 _reflns_number_gt 5872 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXH-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury (Macrae at al., 2006) and POV-RAY (Cason, 2003) ; _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0730P)^2^+1.2846P] 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 7246 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1464 _refine_ls_wR_factor_gt 0.1333 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 S22 S 0.65366(3) 0.99510(3) -0.14648(2) 0.03080(11) Uani 1 1 d . . . O2 O 0.23521(10) 0.60782(11) 0.36964(8) 0.0393(3) Uani 1 1 d . . . O23 O 0.64891(12) 0.96568(12) -0.23200(8) 0.0448(3) Uani 1 1 d . . . O24 O 0.61117(13) 1.10574(10) -0.13503(10) 0.0474(3) Uani 1 1 d . . . O26 O 0.17416(11) 0.26869(13) 0.17352(9) 0.0462(3) Uani 1 1 d . . . H26 H 0.2104 0.2355 0.2200 0.055 Uiso 1 1 calc R . . O34 O 0.23925(10) 0.22375(10) 0.33307(8) 0.0355(3) Uani 1 1 d . . . O35 O 0.15997(11) 0.30365(12) 0.41747(8) 0.0442(3) Uani 1 1 d . . . N4 N 0.21999(12) 0.67041(13) 0.23175(10) 0.0383(3) Uani 1 1 d . . . N13 N 0.32286(10) 0.44635(10) -0.05302(8) 0.0265(2) Uani 1 1 d . . . H13 H 0.3010 0.3853 -0.0863 0.032 Uiso 1 1 calc R . . N15 N 0.25397(11) 0.36094(11) 0.04128(8) 0.0307(3) Uani 1 1 d . . . H15A H 0.2335 0.3022 0.0054 0.037 Uiso 1 1 calc R . . H15B H 0.2409 0.3607 0.0898 0.037 Uiso 1 1 calc R . . C1 C 0.16460(18) 0.7005(2) 0.37135(16) 0.0525(5) Uani 1 1 d . . . H1A H 0.0951 0.6913 0.3237 0.079 Uiso 1 1 calc R . . H1B H 0.1975 0.7740 0.3650 0.079 Uiso 1 1 calc R . . H1C H 0.1529 0.6997 0.4266 0.079 Uiso 1 1 calc R . . C3 C 0.25815(12) 0.59559(14) 0.29671(10) 0.0305(3) Uani 1 1 d . . . C5 C 0.24712(15) 0.65306(14) 0.16138(11) 0.0358(3) Uani 1 1 d . . . H5 H 0.2205 0.7057 0.1145 0.043 Uiso 1 1 calc R . . C6 C 0.31146(12) 0.56308(13) 0.15379(9) 0.0281(3) Uani 1 1 d . . . C7 C 0.35000(13) 0.48646(14) 0.22367(10) 0.0305(3) Uani 1 1 d . . . H7 H 0.3945 0.4233 0.2212 0.037 Uiso 1 1 calc R . . C8 C 0.32314(12) 0.50296(13) 0.29580(9) 0.0297(3) Uani 1 1 d . . . H8 H 0.3487 0.4519 0.3438 0.036 Uiso 1 1 calc R . . C9 C 0.33768(12) 0.55102(12) 0.07434(9) 0.0264(3) Uani 1 1 d . . . C10 C 0.38723(12) 0.63793(12) 0.04589(9) 0.0266(3) Uani 1 1 d . . . H10 H 0.4083 0.7058 0.0799 0.032 Uiso 1 1 calc R . . C11 C 0.40808(11) 0.63027(12) -0.03216(9) 0.0239(2) Uani 1 1 d . . . C12 C 0.37300(12) 0.53155(12) -0.07994(9) 0.0266(3) Uani 1 1 d . . . H12 H 0.3843 0.5230 -0.1332 0.032 Uiso 1 1 calc R . . C14 C 0.30458(11) 0.44987(12) 0.02215(9) 0.0253(3) Uani 1 1 d . . . C16 C 0.46648(11) 0.72149(11) -0.06115(9) 0.0236(2) Uani 1 1 d . . . C17 C 0.52166(13) 0.80948(13) -0.00460(9) 0.0299(3) Uani 1 1 d . . . H17 H 0.5197 0.8121 0.0522 0.036 Uiso 1 1 calc R . . C18 C 0.57922(13) 0.89290(13) -0.03025(9) 0.0303(3) Uani 1 1 d . . . H18 H 0.6153 0.9530 0.0082 0.036 Uiso 1 1 calc R . . C19 C 0.58347(12) 0.88740(12) -0.11280(9) 0.0255(3) Uani 1 1 d . . . C20 C 0.52956(13) 0.80121(12) -0.16996(9) 0.0278(3) Uani 1 1 d . . . H20 H 0.5331 0.7980 -0.2262 0.033 Uiso 1 1 calc R . . C21 C 0.47047(12) 0.71981(12) -0.14455(9) 0.0268(3) Uani 1 1 d . . . H21 H 0.4320 0.6619 -0.1843 0.032 Uiso 1 1 calc R . . C25 C 0.78903(16) 0.98516(18) -0.07552(14) 0.0471(4) Uani 1 1 d . . . H25A H 0.8185 0.9099 -0.0824 0.071 Uiso 1 1 calc R . . H25B H 0.7923 0.9938 -0.0157 0.071 Uiso 1 1 calc R . . H25C H 0.8317 1.0463 -0.0889 0.071 Uiso 1 1 calc R . . C27 C 0.10231(14) 0.34222(17) 0.18788(12) 0.0421(4) Uani 1 1 d . . . C28 C 0.03334(17) 0.4056(3) 0.11754(16) 0.0653(7) Uani 1 1 d . . . H28 H 0.0363 0.3954 0.0615 0.078 Uiso 1 1 calc R . . C29 C -0.03841(18) 0.4826(3) 0.1301(2) 0.0756(9) Uani 1 1 d . . . H29 H -0.0840 0.5263 0.0824 0.091 Uiso 1 1 calc R . . C30 C -0.04563(18) 0.4975(2) 0.2102(2) 0.0690(8) Uani 1 1 d . . . H30 H -0.0963 0.5504 0.2178 0.083 Uiso 1 1 calc R . . C31 C 0.02172(16) 0.43458(17) 0.27982(16) 0.0513(5) Uani 1 1 d . . . H31 H 0.0169 0.4448 0.3353 0.062 Uiso 1 1 calc R . . C32 C 0.09649(13) 0.35654(14) 0.26975(12) 0.0364(4) Uani 1 1 d . . . C33 C 0.16950(13) 0.29109(13) 0.34605(11) 0.0330(3) Uani 1 1 d . . . O1W O 0.0456(4) 0.7906(4) 0.0848(3) 0.1104(12) Uiso 0.68 1 d P A 1 O2W O 0.9820(7) 1.1828(8) -0.0116(6) 0.102(2) Uiso 0.32 1 d P B 2 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 S22 0.0458(2) 0.02082(17) 0.03007(18) 0.00498(12) 0.01884(16) -0.00016(14) O2 0.0426(6) 0.0428(7) 0.0364(6) -0.0034(5) 0.0189(5) 0.0008(5) O23 0.0702(9) 0.0392(7) 0.0331(6) 0.0044(5) 0.0285(6) -0.0043(6) O24 0.0699(9) 0.0208(5) 0.0635(9) 0.0057(5) 0.0383(7) 0.0023(5) O26 0.0484(7) 0.0509(8) 0.0379(7) 0.0146(6) 0.0137(6) -0.0004(6) O34 0.0407(6) 0.0266(5) 0.0359(6) 0.0051(4) 0.0099(5) 0.0098(4) O35 0.0476(7) 0.0415(7) 0.0367(6) -0.0030(5) 0.0067(5) 0.0175(6) N4 0.0444(8) 0.0324(7) 0.0388(7) 0.0030(6) 0.0156(6) 0.0022(6) N13 0.0288(6) 0.0203(5) 0.0267(5) -0.0018(4) 0.0057(4) -0.0031(4) N15 0.0345(6) 0.0253(6) 0.0289(6) 0.0013(5) 0.0073(5) -0.0075(5) C1 0.0504(11) 0.0507(12) 0.0612(13) -0.0142(10) 0.0259(10) 0.0030(9) C3 0.0308(7) 0.0303(7) 0.0299(7) -0.0011(5) 0.0104(5) -0.0062(6) C5 0.0468(9) 0.0283(7) 0.0325(7) 0.0065(6) 0.0146(7) 0.0008(6) C6 0.0331(7) 0.0240(6) 0.0252(6) 0.0010(5) 0.0081(5) -0.0064(5) C7 0.0318(7) 0.0290(7) 0.0273(7) 0.0031(5) 0.0065(5) -0.0041(5) C8 0.0317(7) 0.0295(7) 0.0246(6) 0.0051(5) 0.0061(5) -0.0038(5) C9 0.0304(6) 0.0227(6) 0.0241(6) 0.0012(5) 0.0071(5) -0.0026(5) C10 0.0323(7) 0.0213(6) 0.0245(6) -0.0008(5) 0.0082(5) -0.0031(5) C11 0.0273(6) 0.0199(6) 0.0231(6) 0.0007(5) 0.0072(5) -0.0007(5) C12 0.0293(6) 0.0233(6) 0.0250(6) -0.0009(5) 0.0072(5) -0.0012(5) C14 0.0246(6) 0.0218(6) 0.0244(6) 0.0029(5) 0.0024(5) -0.0012(5) C16 0.0282(6) 0.0190(6) 0.0230(6) 0.0004(4) 0.0082(5) 0.0005(5) C17 0.0418(8) 0.0269(7) 0.0228(6) -0.0033(5) 0.0137(6) -0.0083(6) C18 0.0426(8) 0.0241(6) 0.0262(6) -0.0040(5) 0.0147(6) -0.0084(6) C19 0.0336(7) 0.0192(6) 0.0250(6) 0.0036(5) 0.0120(5) 0.0013(5) C20 0.0396(7) 0.0215(6) 0.0230(6) 0.0019(5) 0.0122(5) 0.0038(5) C21 0.0352(7) 0.0210(6) 0.0230(6) -0.0015(5) 0.0090(5) 0.0000(5) C25 0.0446(10) 0.0448(10) 0.0498(10) 0.0093(8) 0.0143(8) -0.0102(8) C27 0.0306(7) 0.0424(9) 0.0458(9) 0.0180(8) 0.0046(7) -0.0059(7) C28 0.0360(9) 0.0897(18) 0.0600(13) 0.0448(13) 0.0047(9) -0.0025(10) C29 0.0342(10) 0.0854(18) 0.091(2) 0.0574(16) 0.0029(11) 0.0106(11) C30 0.0386(10) 0.0541(14) 0.098(2) 0.0303(13) 0.0042(11) 0.0160(9) C31 0.0379(9) 0.0351(9) 0.0680(13) 0.0059(9) 0.0033(8) 0.0088(7) C32 0.0293(7) 0.0258(7) 0.0435(9) 0.0066(6) 0.0001(6) -0.0005(6) C33 0.0314(7) 0.0222(6) 0.0373(8) -0.0004(6) 0.0021(6) 0.0032(5) _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 S22 O23 1.4348(13) . ? S22 O24 1.4409(13) . ? S22 C25 1.759(2) . ? S22 C19 1.7623(14) . ? O2 C3 1.3528(19) . ? O2 C1 1.432(2) . ? O26 C27 1.360(3) . ? O26 H26 0.8400 . ? O34 C33 1.285(2) . ? O35 C33 1.241(2) . ? N4 C3 1.332(2) . ? N4 C5 1.351(2) . ? N13 C14 1.3499(18) . ? N13 C12 1.3518(19) . ? N13 H13 0.8800 . ? N15 C14 1.3286(18) . ? N15 H15A 0.8800 . ? N15 H15B 0.8800 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3 C8 1.380(2) . ? C5 C6 1.381(2) . ? C5 H5 0.9500 . ? C6 C7 1.402(2) . ? C6 C9 1.481(2) . ? C7 C8 1.375(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.3744(19) . ? C9 C14 1.430(2) . ? C10 C11 1.4166(19) . ? C10 H10 0.9500 . ? C11 C12 1.3747(19) . ? C11 C16 1.4875(19) . ? C12 H12 0.9500 . ? C16 C21 1.3997(19) . ? C16 C17 1.4006(19) . ? C17 C18 1.389(2) . ? C17 H17 0.9500 . ? C18 C19 1.3883(19) . ? C18 H18 0.9500 . ? C19 C20 1.386(2) . ? C20 C21 1.384(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C27 C32 1.394(3) . ? C27 C28 1.403(3) . ? C28 C29 1.372(4) . ? C28 H28 0.9500 . ? C29 C30 1.374(4) . ? C29 H29 0.9500 . ? C30 C31 1.385(3) . ? C30 H30 0.9500 . ? C31 C32 1.395(3) . ? C31 H31 0.9500 . ? C32 C33 1.493(2) . ? 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 O23 S22 O24 117.41(8) . . ? O23 S22 C25 108.50(10) . . ? O24 S22 C25 108.82(10) . . ? O23 S22 C19 107.52(7) . . ? O24 S22 C19 108.40(7) . . ? C25 S22 C19 105.57(8) . . ? C3 O2 C1 116.92(15) . . ? C27 O26 H26 109.5 . . ? C3 N4 C5 117.22(15) . . ? C14 N13 C12 123.53(12) . . ? C14 N13 H13 118.2 . . ? C12 N13 H13 118.2 . . ? C14 N15 H15A 120.0 . . ? C14 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N4 C3 O2 120.66(15) . . ? N4 C3 C8 123.81(14) . . ? O2 C3 C8 115.54(14) . . ? N4 C5 C6 123.63(15) . . ? N4 C5 H5 118.2 . . ? C6 C5 H5 118.2 . . ? C5 C6 C7 117.29(14) . . ? C5 C6 C9 120.00(13) . . ? C7 C6 C9 122.71(14) . . ? C8 C7 C6 119.79(15) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C3 118.27(14) . . ? C7 C8 H8 120.9 . . ? C3 C8 H8 120.9 . . ? C10 C9 C14 118.43(13) . . ? C10 C9 C6 121.77(13) . . ? C14 C9 C6 119.67(12) . . ? C9 C10 C11 122.59(13) . . ? C9 C10 H10 118.7 . . ? C11 C10 H10 118.7 . . ? C12 C11 C10 116.14(13) . . ? C12 C11 C16 120.99(12) . . ? C10 C11 C16 122.85(12) . . ? N13 C12 C11 121.63(13) . . ? N13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? N15 C14 N13 117.89(13) . . ? N15 C14 C9 124.42(13) . . ? N13 C14 C9 117.65(12) . . ? C21 C16 C17 118.29(13) . . ? C21 C16 C11 121.01(12) . . ? C17 C16 C11 120.67(12) . . ? C18 C17 C16 121.05(13) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 119.23(13) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C20 C19 C18 120.82(13) . . ? C20 C19 S22 119.79(11) . . ? C18 C19 S22 119.34(11) . . ? C21 C20 C19 119.60(13) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C16 120.98(13) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? S22 C25 H25A 109.5 . . ? S22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O26 C27 C32 121.99(15) . . ? O26 C27 C28 118.2(2) . . ? C32 C27 C28 119.8(2) . . ? C29 C28 C27 119.7(3) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C30 121.2(2) . . ? C28 C29 H29 119.4 . . ? C30 C29 H29 119.4 . . ? C29 C30 C31 119.3(2) . . ? C29 C30 H30 120.3 . . ? C31 C30 H30 120.3 . . ? C30 C31 C32 121.0(2) . . ? C30 C31 H31 119.5 . . ? C32 C31 H31 119.5 . . ? C27 C32 C31 118.81(17) . . ? C27 C32 C33 121.12(16) . . ? C31 C32 C33 120.07(18) . . ? O35 C33 O34 123.68(14) . . ? O35 C33 C32 119.33(15) . . ? O34 C33 C32 117.00(15) . . ? 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 C5 N4 C3 O2 179.45(15) . . . . ? C5 N4 C3 C8 0.2(2) . . . . ? C1 O2 C3 N4 3.0(2) . . . . ? C1 O2 C3 C8 -177.70(15) . . . . ? C3 N4 C5 C6 -0.1(3) . . . . ? N4 C5 C6 C7 0.0(2) . . . . ? N4 C5 C6 C9 -179.64(15) . . . . ? C5 C6 C7 C8 0.0(2) . . . . ? C9 C6 C7 C8 179.61(13) . . . . ? C6 C7 C8 C3 0.1(2) . . . . ? N4 C3 C8 C7 -0.2(2) . . . . ? O2 C3 C8 C7 -179.51(13) . . . . ? C5 C6 C9 C10 56.9(2) . . . . ? C7 C6 C9 C10 -122.65(16) . . . . ? C5 C6 C9 C14 -118.80(16) . . . . ? C7 C6 C9 C14 61.6(2) . . . . ? C14 C9 C10 C11 -1.0(2) . . . . ? C6 C9 C10 C11 -176.78(13) . . . . ? C9 C10 C11 C12 1.8(2) . . . . ? C9 C10 C11 C16 -176.90(13) . . . . ? C14 N13 C12 C11 -1.0(2) . . . . ? C10 C11 C12 N13 -0.9(2) . . . . ? C16 C11 C12 N13 177.88(13) . . . . ? C12 N13 C14 N15 179.67(13) . . . . ? C12 N13 C14 C9 1.8(2) . . . . ? C10 C9 C14 N15 -178.52(14) . . . . ? C6 C9 C14 N15 -2.6(2) . . . . ? C10 C9 C14 N13 -0.8(2) . . . . ? C6 C9 C14 N13 175.06(13) . . . . ? C12 C11 C16 C21 11.6(2) . . . . ? C10 C11 C16 C21 -169.71(13) . . . . ? C12 C11 C16 C17 -166.46(14) . . . . ? C10 C11 C16 C17 12.2(2) . . . . ? C21 C16 C17 C18 -0.2(2) . . . . ? C11 C16 C17 C18 177.95(14) . . . . ? C16 C17 C18 C19 -1.2(2) . . . . ? C17 C18 C19 C20 1.2(2) . . . . ? C17 C18 C19 S22 178.45(12) . . . . ? O23 S22 C19 C20 -5.06(15) . . . . ? O24 S22 C19 C20 122.80(13) . . . . ? C25 S22 C19 C20 -120.73(14) . . . . ? O23 S22 C19 C18 177.62(13) . . . . ? O24 S22 C19 C18 -54.52(15) . . . . ? C25 S22 C19 C18 61.95(15) . . . . ? C18 C19 C20 C21 0.2(2) . . . . ? S22 C19 C20 C21 -177.08(11) . . . . ? C19 C20 C21 C16 -1.6(2) . . . . ? C17 C16 C21 C20 1.6(2) . . . . ? C11 C16 C21 C20 -176.56(13) . . . . ? O26 C27 C28 C29 -178.5(2) . . . . ? C32 C27 C28 C29 0.9(3) . . . . ? C27 C28 C29 C30 -1.2(4) . . . . ? C28 C29 C30 C31 0.8(4) . . . . ? C29 C30 C31 C32 0.0(4) . . . . ? O26 C27 C32 C31 179.18(17) . . . . ? C28 C27 C32 C31 -0.2(3) . . . . ? O26 C27 C32 C33 -0.1(3) . . . . ? C28 C27 C32 C33 -179.43(17) . . . . ? C30 C31 C32 C27 -0.2(3) . . . . ? C30 C31 C32 C33 179.02(19) . . . . ? C27 C32 C33 O35 -178.01(16) . . . . ? C31 C32 C33 O35 2.8(2) . . . . ? C27 C32 C33 O34 1.7(2) . . . . ? C31 C32 C33 O34 -177.49(16) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.58 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.466 _refine_diff_density_min -0.717 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 959479' ####################################################################### # # 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_c:\dyanne~1\2013\007\s3sube~1\007suba _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-6(-Methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)- pyridine-2-amine. octanedioate salt ; _chemical_name_common ? _chemical_melting_point 419 _chemical_formula_moiety 'C18 H18 N3 O3 S1, C8 H13 O4' _chemical_formula_sum 'C26 H31 N3 O7 S' _chemical_formula_weight 529.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4192(7) _cell_length_b 12.1987(15) _cell_length_c 19.705(3) _cell_angle_alpha 75.627(2) _cell_angle_beta 88.814(2) _cell_angle_gamma 89.651(2) _cell_volume 1261.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6897 _cell_measurement_theta_min 1.72 _cell_measurement_theta_max 29.34 _exptl_crystal_description rods _exptl_crystal_colour 'translucent yellow' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9585 _exptl_absorpt_correction_T_max 0.9707 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex II Duo diffractometer' _diffrn_measurement_method 'phi- and omega-scans of 0.5 deg.' _diffrn_reflns_number 26058 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0654 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 29.34 _reflns_number_total 6897 _reflns_number_gt 4483 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXH-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury (Macrae at al., 2006) and POV-RAY (Cason, 2003) ; _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0439P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6897 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_restrained_S_all 0.905 _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 S22 S 0.55487(7) 0.70101(3) -0.12365(2) 0.02417(10) Uani 1 1 d . . . O1A O 0.3252(2) 0.62760(9) 0.45526(6) 0.0330(3) Uani 1 1 d . . . O1B O -0.0336(3) 0.88634(11) 0.26879(7) 0.0509(4) Uani 1 1 d . . . H1B H 0.0744 0.8436 0.2915 0.061 Uiso 1 1 calc R . . O2 O 1.5987(2) 0.15123(9) 0.37920(6) 0.0339(3) Uani 1 1 d . . . O3A O 0.2613(2) 0.74362(10) 0.35099(6) 0.0377(3) Uani 1 1 d . . . O3B O 0.1298(3) 0.82743(13) 0.18065(7) 0.0604(5) Uani 1 1 d . . . O23 O 0.6672(2) 0.60981(9) -0.14743(6) 0.0309(3) Uani 1 1 d . . . O24 O 0.29786(19) 0.72612(10) -0.13811(6) 0.0352(3) Uani 1 1 d . . . N4 N 1.2565(2) 0.22061(10) 0.31446(7) 0.0253(3) Uani 1 1 d . . . N13 N 0.5961(2) 0.62818(10) 0.30052(7) 0.0247(3) Uani 1 1 d . . . H13 H 0.5095 0.6666 0.3251 0.030 Uiso 1 1 calc R . . N15 N 0.7600(2) 0.53371(11) 0.40495(7) 0.0267(3) Uani 1 1 d . . . H15A H 0.6643 0.5747 0.4257 0.032 Uiso 1 1 calc R . . H15B H 0.8596 0.4829 0.4300 0.032 Uiso 1 1 calc R . . C1 C 1.6344(3) 0.07563(15) 0.33430(9) 0.0378(4) Uani 1 1 d . . . H1A H 1.4866 0.0289 0.3363 0.057 Uiso 1 1 calc R . . H1D H 1.7769 0.0267 0.3500 0.057 Uiso 1 1 calc R . . H1C H 1.6640 0.1197 0.2860 0.057 Uiso 1 1 calc R . . C2A C 0.2140(3) 0.70831(13) 0.41675(8) 0.0277(4) Uani 1 1 d . . . C2B C -0.0198(3) 0.88274(13) 0.20287(9) 0.0304(4) Uani 1 1 d . . . C3 C 1.4165(3) 0.22941(13) 0.36239(8) 0.0250(3) Uani 1 1 d . . . C4A C 0.0215(3) 0.77207(13) 0.44775(8) 0.0294(4) Uani 1 1 d . . . H4A1 H -0.0299 0.7265 0.4947 0.035 Uiso 1 1 calc R . . H4A2 H -0.1254 0.7847 0.4177 0.035 Uiso 1 1 calc R . . C4B C -0.2144(3) 0.95334(14) 0.15882(9) 0.0316(4) Uani 1 1 d . . . H4B1 H -0.1920 1.0332 0.1602 0.038 Uiso 1 1 calc R . . H4B2 H -0.3784 0.9287 0.1800 0.038 Uiso 1 1 calc R . . C5 C 1.0858(3) 0.30262(12) 0.29755(8) 0.0240(3) Uani 1 1 d . . . H5 H 0.9672 0.2963 0.2639 0.029 Uiso 1 1 calc R . . C5A C 0.1220(3) 0.88597(13) 0.45390(8) 0.0271(4) Uani 1 1 d . . . H5A1 H 0.2882 0.8746 0.4744 0.033 Uiso 1 1 calc R . . H5A2 H 0.1388 0.9373 0.4065 0.033 Uiso 1 1 calc R . . C5B C -0.2128(3) 0.94725(15) 0.08275(9) 0.0358(4) Uani 1 1 d . . . H5B1 H -0.3672 0.9820 0.0612 0.043 Uiso 1 1 calc R . . H5B2 H -0.2144 0.8666 0.0816 0.043 Uiso 1 1 calc R . . C6 C 1.0708(3) 0.39597(12) 0.32585(8) 0.0219(3) Uani 1 1 d . . . C6A C -0.0441(3) 0.94147(12) 0.49914(8) 0.0268(4) Uani 1 1 d . . . H6A1 H -0.2136 0.9472 0.4808 0.032 Uiso 1 1 calc R . . H6A2 H -0.0503 0.8929 0.5475 0.032 Uiso 1 1 calc R . . C6B C 0.0042(3) 1.00464(14) 0.03776(8) 0.0311(4) Uani 1 1 d . . . H6B1 H 0.0060 1.0856 0.0381 0.037 Uiso 1 1 calc R . . H6B2 H 0.1595 0.9701 0.0587 0.037 Uiso 1 1 calc R . . C7 C 1.2376(3) 0.39952(13) 0.37851(8) 0.0243(3) Uani 1 1 d . . . H7 H 1.2313 0.4601 0.4009 0.029 Uiso 1 1 calc R . . C8 C 1.4110(3) 0.31501(13) 0.39791(8) 0.0258(3) Uani 1 1 d . . . H8 H 1.5232 0.3151 0.4343 0.031 Uiso 1 1 calc R . . C9 C 0.8962(3) 0.48842(12) 0.29471(8) 0.0217(3) Uani 1 1 d . . . C10 C 0.8631(3) 0.51561(12) 0.22340(8) 0.0232(3) Uani 1 1 d . . . H10 H 0.9594 0.4767 0.1959 0.028 Uiso 1 1 calc R . . C11 C 0.6937(3) 0.59814(12) 0.18886(8) 0.0222(3) Uani 1 1 d . . . C12 C 0.5624(3) 0.65267(12) 0.23087(8) 0.0246(3) Uani 1 1 d . . . H12 H 0.4454 0.7089 0.2104 0.030 Uiso 1 1 calc R . . C14 C 0.7538(3) 0.54866(12) 0.33517(8) 0.0225(3) Uani 1 1 d . . . C16 C 0.6583(3) 0.62483(12) 0.11240(8) 0.0219(3) Uani 1 1 d . . . C17 C 0.4487(3) 0.68209(13) 0.08201(8) 0.0289(4) Uani 1 1 d . . . H17 H 0.3261 0.7045 0.1110 0.035 Uiso 1 1 calc R . . C18 C 0.4164(3) 0.70667(13) 0.01039(8) 0.0289(4) Uani 1 1 d . . . H18 H 0.2732 0.7462 -0.0095 0.035 Uiso 1 1 calc R . . C19 C 0.5930(3) 0.67356(13) -0.03232(8) 0.0234(3) Uani 1 1 d . . . C20 C 0.8039(3) 0.61811(14) -0.00323(8) 0.0309(4) Uani 1 1 d . . . H20 H 0.9268 0.5965 -0.0325 0.037 Uiso 1 1 calc R . . C21 C 0.8354(3) 0.59434(14) 0.06820(8) 0.0299(4) Uani 1 1 d . . . H21 H 0.9808 0.5564 0.0877 0.036 Uiso 1 1 calc R . . C25 C 0.7276(3) 0.82417(13) -0.15728(8) 0.0277(4) Uani 1 1 d . . . H25A H 0.9004 0.8102 -0.1440 0.042 Uiso 1 1 calc R . . H25B H 0.6618 0.8856 -0.1382 0.042 Uiso 1 1 calc R . . H25C H 0.7172 0.8456 -0.2085 0.042 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 S22 0.0237(2) 0.0305(2) 0.0186(2) -0.00682(16) -0.00262(15) 0.00487(16) O1A 0.0444(7) 0.0341(6) 0.0210(6) -0.0078(5) -0.0054(5) 0.0151(5) O1B 0.0670(10) 0.0580(9) 0.0278(7) -0.0111(6) -0.0064(6) 0.0378(7) O2 0.0366(7) 0.0385(7) 0.0275(7) -0.0096(5) -0.0086(5) 0.0191(5) O3A 0.0520(8) 0.0404(7) 0.0191(6) -0.0055(5) 0.0031(5) 0.0236(6) O3B 0.0707(10) 0.0779(10) 0.0328(8) -0.0149(7) -0.0063(7) 0.0523(8) O23 0.0391(7) 0.0301(6) 0.0256(6) -0.0111(5) 0.0002(5) 0.0049(5) O24 0.0229(6) 0.0558(8) 0.0262(6) -0.0088(6) -0.0052(5) 0.0057(5) N4 0.0284(7) 0.0267(7) 0.0204(7) -0.0054(5) -0.0017(6) 0.0081(6) N13 0.0308(7) 0.0252(7) 0.0190(7) -0.0077(5) 0.0009(6) 0.0088(6) N15 0.0309(7) 0.0314(7) 0.0193(7) -0.0095(6) -0.0021(6) 0.0104(6) C1 0.0413(11) 0.0389(10) 0.0346(10) -0.0119(8) -0.0032(8) 0.0184(8) C2A 0.0363(9) 0.0267(8) 0.0224(9) -0.0105(7) -0.0007(7) 0.0062(7) C2B 0.0345(10) 0.0287(8) 0.0269(9) -0.0052(7) 0.0004(7) 0.0063(7) C3 0.0254(8) 0.0283(8) 0.0189(8) -0.0016(6) 0.0008(6) 0.0074(7) C4A 0.0354(9) 0.0288(8) 0.0251(9) -0.0090(7) 0.0052(7) 0.0059(7) C4B 0.0273(9) 0.0322(9) 0.0334(10) -0.0043(7) -0.0017(7) 0.0052(7) C5 0.0256(8) 0.0285(8) 0.0183(8) -0.0064(6) -0.0027(6) 0.0043(6) C5A 0.0312(9) 0.0268(8) 0.0239(9) -0.0078(7) 0.0025(7) 0.0079(7) C5B 0.0304(10) 0.0400(10) 0.0363(11) -0.0075(8) -0.0073(8) 0.0014(8) C6 0.0232(8) 0.0256(8) 0.0160(7) -0.0036(6) 0.0002(6) 0.0055(6) C6A 0.0322(9) 0.0272(8) 0.0219(8) -0.0082(7) 0.0043(7) 0.0063(7) C6B 0.0308(9) 0.0328(9) 0.0298(9) -0.0076(7) -0.0082(7) 0.0035(7) C7 0.0263(8) 0.0267(8) 0.0205(8) -0.0073(6) 0.0012(6) 0.0023(6) C8 0.0254(8) 0.0325(9) 0.0187(8) -0.0047(7) -0.0033(6) 0.0017(7) C9 0.0224(8) 0.0226(7) 0.0202(8) -0.0055(6) -0.0001(6) 0.0034(6) C10 0.0248(8) 0.0247(8) 0.0206(8) -0.0068(6) 0.0014(6) 0.0054(6) C11 0.0239(8) 0.0229(7) 0.0192(8) -0.0041(6) 0.0004(6) 0.0024(6) C12 0.0281(9) 0.0247(8) 0.0204(8) -0.0044(6) -0.0015(7) 0.0065(6) C14 0.0237(8) 0.0229(7) 0.0211(8) -0.0061(6) -0.0014(6) 0.0023(6) C16 0.0243(8) 0.0213(7) 0.0194(8) -0.0040(6) -0.0006(6) 0.0039(6) C17 0.0271(9) 0.0376(9) 0.0228(9) -0.0093(7) 0.0011(7) 0.0107(7) C18 0.0260(9) 0.0371(9) 0.0237(9) -0.0075(7) -0.0042(7) 0.0126(7) C19 0.0247(8) 0.0270(8) 0.0184(8) -0.0053(6) -0.0017(6) 0.0041(6) C20 0.0285(9) 0.0432(10) 0.0205(8) -0.0075(7) 0.0009(7) 0.0146(8) C21 0.0276(9) 0.0403(9) 0.0210(8) -0.0063(7) -0.0025(7) 0.0145(7) C25 0.0303(9) 0.0312(9) 0.0217(8) -0.0069(7) -0.0029(7) 0.0049(7) _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 S22 O23 1.4377(10) . ? S22 O24 1.4432(11) . ? S22 C25 1.7520(17) . ? S22 C19 1.7633(16) . ? O1A C2A 1.2448(17) . ? O1B C2B 1.311(2) . ? O1B H1B 0.8400 . ? O2 C3 1.3559(16) . ? O2 C1 1.4375(18) . ? O3A C2A 1.2810(19) . ? O3B C2B 1.1954(18) . ? N4 C3 1.319(2) . ? N4 C5 1.3431(17) . ? N13 C12 1.3463(19) . ? N13 C14 1.3501(18) . ? N13 H13 0.8800 . ? N15 C14 1.3426(19) . ? N15 H15A 0.8800 . ? N15 H15B 0.8800 . ? C1 H1A 0.9800 . ? C1 H1D 0.9800 . ? C1 H1C 0.9800 . ? C2A C4A 1.505(2) . ? C2B C4B 1.505(2) . ? C3 C8 1.394(2) . ? C4A C5A 1.529(2) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C4B C5B 1.519(2) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5 C6 1.388(2) . ? C5 H5 0.9500 . ? C5A C6A 1.5239(19) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C5B C6B 1.522(2) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6 C7 1.399(2) . ? C6 C9 1.4871(19) . ? C6A C6A 1.517(3) 2_576 ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C6B C6B 1.522(3) 2_575 ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7 C8 1.378(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.377(2) . ? C9 C14 1.4247(19) . ? C10 C11 1.4120(19) . ? C10 H10 0.9500 . ? C11 C12 1.3700(19) . ? C11 C16 1.477(2) . ? C12 H12 0.9500 . ? C16 C21 1.393(2) . ? C16 C17 1.396(2) . ? C17 C18 1.383(2) . ? C17 H17 0.9500 . ? C18 C19 1.385(2) . ? C18 H18 0.9500 . ? C19 C20 1.385(2) . ? C20 C21 1.379(2) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? 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 O23 S22 O24 118.56(7) . . ? O23 S22 C25 108.54(7) . . ? O24 S22 C25 108.65(7) . . ? O23 S22 C19 108.04(7) . . ? O24 S22 C19 108.14(7) . . ? C25 S22 C19 103.94(8) . . ? C2B O1B H1B 109.5 . . ? C3 O2 C1 117.10(12) . . ? C3 N4 C5 116.96(13) . . ? C12 N13 C14 124.36(12) . . ? C12 N13 H13 117.8 . . ? C14 N13 H13 117.8 . . ? C14 N15 H15A 120.0 . . ? C14 N15 H15B 120.0 . . ? H15A N15 H15B 120.0 . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1D 109.5 . . ? H1A C1 H1D 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1D C1 H1C 109.5 . . ? O1A C2A O3A 122.93(13) . . ? O1A C2A C4A 119.88(14) . . ? O3A C2A C4A 117.14(13) . . ? O3B C2B O1B 123.21(15) . . ? O3B C2B C4B 123.81(16) . . ? O1B C2B C4B 112.97(13) . . ? N4 C3 O2 119.18(13) . . ? N4 C3 C8 123.99(13) . . ? O2 C3 C8 116.83(14) . . ? C2A C4A C5A 110.86(14) . . ? C2A C4A H4A1 109.5 . . ? C5A C4A H4A1 109.5 . . ? C2A C4A H4A2 109.5 . . ? C5A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 108.1 . . ? C2B C4B C5B 114.74(13) . . ? C2B C4B H4B1 108.6 . . ? C5B C4B H4B1 108.6 . . ? C2B C4B H4B2 108.6 . . ? C5B C4B H4B2 108.6 . . ? H4B1 C4B H4B2 107.6 . . ? N4 C5 C6 124.49(14) . . ? N4 C5 H5 117.8 . . ? C6 C5 H5 117.8 . . ? C6A C5A C4A 112.44(13) . . ? C6A C5A H5A1 109.1 . . ? C4A C5A H5A1 109.1 . . ? C6A C5A H5A2 109.1 . . ? C4A C5A H5A2 109.1 . . ? H5A1 C5A H5A2 107.8 . . ? C4B C5B C6B 115.78(14) . . ? C4B C5B H5B1 108.3 . . ? C6B C5B H5B1 108.3 . . ? C4B C5B H5B2 108.3 . . ? C6B C5B H5B2 108.3 . . ? H5B1 C5B H5B2 107.4 . . ? C5 C6 C7 116.59(13) . . ? C5 C6 C9 118.49(13) . . ? C7 C6 C9 124.72(13) . . ? C6A C6A C5A 112.67(16) 2_576 . ? C6A C6A H6A1 109.1 2_576 . ? C5A C6A H6A1 109.1 . . ? C6A C6A H6A2 109.1 2_576 . ? C5A C6A H6A2 109.1 . . ? H6A1 C6A H6A2 107.8 . . ? C6B C6B C5B 113.31(18) 2_575 . ? C6B C6B H6B1 108.9 2_575 . ? C5B C6B H6B1 108.9 . . ? C6B C6B H6B2 108.9 2_575 . ? C5B C6B H6B2 108.9 . . ? H6B1 C6B H6B2 107.7 . . ? C8 C7 C6 119.92(14) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C3 117.86(14) . . ? C7 C8 H8 121.1 . . ? C3 C8 H8 121.1 . . ? C10 C9 C14 117.70(13) . . ? C10 C9 C6 118.88(12) . . ? C14 C9 C6 123.39(13) . . ? C9 C10 C11 123.55(13) . . ? C9 C10 H10 118.2 . . ? C11 C10 H10 118.2 . . ? C12 C11 C10 115.74(14) . . ? C12 C11 C16 121.58(13) . . ? C10 C11 C16 122.68(13) . . ? N13 C12 C11 121.28(13) . . ? N13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? N15 C14 N13 116.40(12) . . ? N15 C14 C9 126.24(13) . . ? N13 C14 C9 117.36(13) . . ? C21 C16 C17 117.88(14) . . ? C21 C16 C11 120.76(13) . . ? C17 C16 C11 121.35(13) . . ? C18 C17 C16 121.09(14) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 119.92(14) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 C20 119.81(14) . . ? C18 C19 S22 121.13(11) . . ? C20 C19 S22 119.05(11) . . ? C21 C20 C19 119.93(14) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C16 121.34(14) . . ? C20 C21 H21 119.3 . . ? C16 C21 H21 119.3 . . ? S22 C25 H25A 109.5 . . ? S22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N4 C3 O2 -177.32(14) . . . . ? C5 N4 C3 C8 2.9(2) . . . . ? C1 O2 C3 N4 11.5(2) . . . . ? C1 O2 C3 C8 -168.70(15) . . . . ? O1A C2A C4A C5A 103.74(18) . . . . ? O3A C2A C4A C5A -73.78(19) . . . . ? O3B C2B C4B C5B 1.5(3) . . . . ? O1B C2B C4B C5B -177.25(15) . . . . ? C3 N4 C5 C6 1.4(2) . . . . ? C2A C4A C5A C6A -167.45(13) . . . . ? C2B C4B C5B C6B -70.48(19) . . . . ? N4 C5 C6 C7 -4.0(2) . . . . ? N4 C5 C6 C9 171.07(14) . . . . ? C4A C5A C6A C6A -175.56(16) . . . 2_576 ? C4B C5B C6B C6B 179.82(16) . . . 2_575 ? C5 C6 C7 C8 2.3(2) . . . . ? C9 C6 C7 C8 -172.40(14) . . . . ? C6 C7 C8 C3 1.5(2) . . . . ? N4 C3 C8 C7 -4.4(2) . . . . ? O2 C3 C8 C7 175.86(14) . . . . ? C5 C6 C9 C10 -36.4(2) . . . . ? C7 C6 C9 C10 138.26(16) . . . . ? C5 C6 C9 C14 141.53(16) . . . . ? C7 C6 C9 C14 -43.8(2) . . . . ? C14 C9 C10 C11 -1.1(2) . . . . ? C6 C9 C10 C11 176.95(14) . . . . ? C9 C10 C11 C12 0.9(2) . . . . ? C9 C10 C11 C16 -179.06(15) . . . . ? C14 N13 C12 C11 -1.2(2) . . . . ? C10 C11 C12 N13 0.2(2) . . . . ? C16 C11 C12 N13 -179.80(14) . . . . ? C12 N13 C14 N15 -178.60(14) . . . . ? C12 N13 C14 C9 1.1(2) . . . . ? C10 C9 C14 N15 179.71(15) . . . . ? C6 C9 C14 N15 1.8(3) . . . . ? C10 C9 C14 N13 0.1(2) . . . . ? C6 C9 C14 N13 -177.85(14) . . . . ? C12 C11 C16 C21 161.60(15) . . . . ? C10 C11 C16 C21 -18.4(2) . . . . ? C12 C11 C16 C17 -17.8(2) . . . . ? C10 C11 C16 C17 162.20(15) . . . . ? C21 C16 C17 C18 0.7(2) . . . . ? C11 C16 C17 C18 -179.88(15) . . . . ? C16 C17 C18 C19 0.5(3) . . . . ? C17 C18 C19 C20 -1.4(3) . . . . ? C17 C18 C19 S22 178.73(13) . . . . ? O23 S22 C19 C18 -147.01(13) . . . . ? O24 S22 C19 C18 -17.53(16) . . . . ? C25 S22 C19 C18 97.82(14) . . . . ? O23 S22 C19 C20 33.13(15) . . . . ? O24 S22 C19 C20 162.61(13) . . . . ? C25 S22 C19 C20 -82.05(14) . . . . ? C18 C19 C20 C21 1.1(3) . . . . ? S22 C19 C20 C21 -179.02(14) . . . . ? C19 C20 C21 C16 0.1(3) . . . . ? C17 C16 C21 C20 -1.0(2) . . . . ? C11 C16 C21 C20 179.58(16) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 29.34 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.272 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 959480'