# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # 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_k10farm2 _database_code_depnum_ccdc_archive 'CCDC 926530' #TrackingRef 'bigcif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 N4 S' _chemical_formula_weight 282.36 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7950(2) _cell_length_b 14.7280(3) _cell_length_c 10.0360(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.768(1) _cell_angle_gamma 90.00 _cell_volume 1378.74(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 14347 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description colorless _exptl_crystal_colour block _exptl_crystal_size_max .35 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.230 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.716 _exptl_absorpt_correction_T_max 0.938 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24456 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3152 _reflns_number_gt 2385 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick 1997)' _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. H1A and H1B located and refined at a distance of 0.98\%A from N1. ; _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^+0.4856P] 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 3152 _refine_ls_number_parameters 189 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.46282(4) 0.17783(3) 1.07454(4) 0.03050(14) Uani 1 1 d . . . N1 N 0.23668(15) 0.24736(10) 0.88053(15) 0.0291(3) Uani 1 1 d D . . N2 N 0.45409(13) 0.27819(9) 0.85211(13) 0.0214(3) Uani 1 1 d . . . N3 N 0.38110(13) 0.32553(8) 0.73077(13) 0.0205(3) Uani 1 1 d . . . N4 N 0.48978(14) 0.35498(9) 0.43074(13) 0.0235(3) Uani 1 1 d . . . C1 C 0.37905(16) 0.23688(10) 0.92880(16) 0.0219(3) Uani 1 1 d . . . C2 C 0.60912(15) 0.27330(10) 0.87030(16) 0.0205(3) Uani 1 1 d . . . H2 H 0.6473 0.2117 0.9040 0.025 Uiso 1 1 calc R . . C3 C 0.69237(16) 0.34632(10) 0.96889(16) 0.0207(3) Uani 1 1 d . . . C4 C 0.62794(18) 0.40475(11) 1.03987(16) 0.0268(4) Uani 1 1 d . . . H4 H 0.5280 0.3999 1.0268 0.032 Uiso 1 1 calc R . . C5 C 0.7078(2) 0.47040(13) 1.12989(18) 0.0349(4) Uani 1 1 d . . . H5 H 0.6621 0.5101 1.1775 0.042 Uiso 1 1 calc R . . C6 C 0.8530(2) 0.47811(13) 1.1503(2) 0.0389(5) Uani 1 1 d . . . H6 H 0.9078 0.5224 1.2130 0.047 Uiso 1 1 calc R . . C7 C 0.91851(19) 0.42095(12) 1.0789(2) 0.0357(4) Uani 1 1 d . . . H7 H 1.0184 0.4264 1.0918 0.043 Uiso 1 1 calc R . . C8 C 0.83876(17) 0.35582(11) 0.98865(18) 0.0273(4) Uani 1 1 d . . . H8 H 0.8845 0.3171 0.9396 0.033 Uiso 1 1 calc R . . C9 C 0.61005(16) 0.28849(11) 0.71863(16) 0.0220(3) Uani 1 1 d . . . H9A H 0.6905 0.3280 0.7147 0.026 Uiso 1 1 calc R . . H9B H 0.6150 0.2303 0.6708 0.026 Uiso 1 1 calc R . . C10 C 0.46755(15) 0.33459(10) 0.65744(15) 0.0187(3) Uani 1 1 d . . . C11 C 0.41951(15) 0.37995(10) 0.52084(15) 0.0186(3) Uani 1 1 d . . . C12 C 0.44274(18) 0.38974(11) 0.30101(17) 0.0279(4) Uani 1 1 d . . . H12 H 0.4889 0.3712 0.2349 0.033 Uiso 1 1 calc R . . C13 C 0.33097(18) 0.45098(11) 0.25817(17) 0.0277(4) Uani 1 1 d . . . H13 H 0.3018 0.4739 0.1653 0.033 Uiso 1 1 calc R . . C14 C 0.26263(17) 0.47816(11) 0.35308(17) 0.0266(4) Uani 1 1 d . . . H14 H 0.1868 0.5212 0.3272 0.032 Uiso 1 1 calc R . . C15 C 0.30629(16) 0.44174(10) 0.48662(17) 0.0236(3) Uani 1 1 d . . . H15 H 0.2601 0.4585 0.5535 0.028 Uiso 1 1 calc R . . H1A H 0.1791(19) 0.2159(13) 0.930(2) 0.055(6) Uiso 1 1 d D . . H1B H 0.1915(19) 0.2747(13) 0.7894(11) 0.047(6) 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 S1 0.0282(2) 0.0362(3) 0.0246(2) 0.01002(18) 0.00435(17) -0.00527(18) N1 0.0208(7) 0.0419(8) 0.0252(8) 0.0079(6) 0.0080(6) -0.0041(6) N2 0.0170(6) 0.0273(7) 0.0197(7) 0.0044(5) 0.0052(5) -0.0010(5) N3 0.0213(6) 0.0226(6) 0.0163(6) 0.0004(5) 0.0039(5) -0.0019(5) N4 0.0251(7) 0.0275(7) 0.0202(7) 0.0010(5) 0.0104(6) 0.0002(6) C1 0.0215(8) 0.0249(8) 0.0194(8) -0.0011(6) 0.0064(6) -0.0052(6) C2 0.0164(7) 0.0233(8) 0.0219(8) 0.0025(6) 0.0060(6) 0.0005(6) C3 0.0219(8) 0.0225(8) 0.0169(7) 0.0060(6) 0.0044(6) 0.0005(6) C4 0.0275(8) 0.0330(9) 0.0205(8) 0.0009(7) 0.0085(7) -0.0016(7) C5 0.0426(10) 0.0363(10) 0.0261(9) -0.0074(8) 0.0107(8) -0.0007(8) C6 0.0402(11) 0.0334(10) 0.0349(10) -0.0054(8) -0.0007(9) -0.0077(8) C7 0.0237(9) 0.0317(9) 0.0437(11) 0.0022(8) -0.0015(8) -0.0044(7) C8 0.0238(8) 0.0239(8) 0.0325(9) 0.0031(7) 0.0060(7) 0.0022(7) C9 0.0208(8) 0.0249(8) 0.0211(8) -0.0017(6) 0.0072(6) 0.0000(6) C10 0.0195(7) 0.0194(7) 0.0179(7) -0.0029(6) 0.0066(6) -0.0019(6) C11 0.0193(7) 0.0203(7) 0.0170(8) -0.0026(6) 0.0065(6) -0.0048(6) C12 0.0326(9) 0.0334(9) 0.0205(8) 0.0013(7) 0.0126(7) 0.0000(7) C13 0.0312(9) 0.0285(9) 0.0210(8) 0.0065(7) 0.0043(7) -0.0024(7) C14 0.0233(8) 0.0240(8) 0.0292(9) 0.0020(7) 0.0032(7) 0.0011(6) C15 0.0239(8) 0.0237(8) 0.0245(8) -0.0031(6) 0.0093(7) -0.0013(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.6842(16) . ? N1 C1 1.338(2) . ? N1 H1A 0.974(5) . ? N1 H1B 0.974(5) . ? N2 C1 1.359(2) . ? N2 N3 1.3960(17) . ? N2 C2 1.4748(19) . ? N3 C10 1.2871(19) . ? N4 C12 1.343(2) . ? N4 C11 1.3441(19) . ? C2 C3 1.519(2) . ? C2 C9 1.541(2) . ? C2 H2 1.0000 . ? C3 C4 1.386(2) . ? C3 C8 1.393(2) . ? C4 C5 1.390(2) . ? C4 H4 0.9500 . ? C5 C6 1.379(3) . ? C5 H5 0.9500 . ? C6 C7 1.384(3) . ? C6 H6 0.9500 . ? C7 C8 1.385(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.504(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.468(2) . ? C11 C15 1.394(2) . ? C12 C13 1.382(2) . ? C12 H12 0.9500 . ? C13 C14 1.380(2) . ? C13 H13 0.9500 . ? C14 C15 1.385(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 H1A 117.5(13) . . ? C1 N1 H1B 120.9(12) . . ? H1A N1 H1B 120.4(17) . . ? C1 N2 N3 119.73(12) . . ? C1 N2 C2 128.48(13) . . ? N3 N2 C2 111.48(11) . . ? C10 N3 N2 107.42(12) . . ? C12 N4 C11 116.95(14) . . ? N1 C1 N2 115.29(14) . . ? N1 C1 S1 123.48(12) . . ? N2 C1 S1 121.23(12) . . ? N2 C2 C3 111.95(12) . . ? N2 C2 C9 100.77(11) . . ? C3 C2 C9 112.13(12) . . ? N2 C2 H2 110.5 . . ? C3 C2 H2 110.5 . . ? C9 C2 H2 110.5 . . ? C4 C3 C8 118.34(15) . . ? C4 C3 C2 122.43(14) . . ? C8 C3 C2 119.23(14) . . ? C3 C4 C5 120.80(16) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 120.29(17) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 119.55(17) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C8 120.13(16) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C3 120.87(16) . . ? C7 C8 H8 119.6 . . ? C3 C8 H8 119.6 . . ? C10 C9 C2 100.62(12) . . ? C10 C9 H9A 111.6 . . ? C2 C9 H9A 111.6 . . ? C10 C9 H9B 111.6 . . ? C2 C9 H9B 111.6 . . ? H9A C9 H9B 109.4 . . ? N3 C10 C11 120.14(13) . . ? N3 C10 C9 114.21(13) . . ? C11 C10 C9 125.44(13) . . ? N4 C11 C15 123.04(14) . . ? N4 C11 C10 114.83(13) . . ? C15 C11 C10 122.10(13) . . ? N4 C12 C13 123.73(15) . . ? N4 C12 H12 118.1 . . ? C13 C12 H12 118.1 . . ? C14 C13 C12 118.66(15) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C15 118.96(15) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C14 C15 C11 118.60(14) . . ? C14 C15 H15 120.7 . . ? C11 C15 H15 120.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N2 N3 C10 -161.42(14) . . . . ? C2 N2 N3 C10 12.75(16) . . . . ? N3 N2 C1 N1 -1.3(2) . . . . ? C2 N2 C1 N1 -174.40(14) . . . . ? N3 N2 C1 S1 179.10(11) . . . . ? C2 N2 C1 S1 6.0(2) . . . . ? C1 N2 C2 C3 -89.28(18) . . . . ? N3 N2 C2 C3 97.19(14) . . . . ? C1 N2 C2 C9 151.37(15) . . . . ? N3 N2 C2 C9 -22.16(15) . . . . ? N2 C2 C3 C4 4.7(2) . . . . ? C9 C2 C3 C4 117.11(16) . . . . ? N2 C2 C3 C8 -174.87(13) . . . . ? C9 C2 C3 C8 -62.45(18) . . . . ? C8 C3 C4 C5 -0.8(2) . . . . ? C2 C3 C4 C5 179.62(15) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C4 C5 C6 C7 1.0(3) . . . . ? C5 C6 C7 C8 -0.7(3) . . . . ? C6 C7 C8 C3 -0.4(3) . . . . ? C4 C3 C8 C7 1.1(2) . . . . ? C2 C3 C8 C7 -179.28(15) . . . . ? N2 C2 C9 C10 21.41(14) . . . . ? C3 C2 C9 C10 -97.81(14) . . . . ? N2 N3 C10 C11 178.38(12) . . . . ? N2 N3 C10 C9 3.42(17) . . . . ? C2 C9 C10 N3 -16.74(16) . . . . ? C2 C9 C10 C11 168.61(13) . . . . ? C12 N4 C11 C15 -2.5(2) . . . . ? C12 N4 C11 C10 175.33(13) . . . . ? N3 C10 C11 N4 -154.21(14) . . . . ? C9 C10 C11 N4 20.1(2) . . . . ? N3 C10 C11 C15 23.7(2) . . . . ? C9 C10 C11 C15 -161.97(14) . . . . ? C11 N4 C12 C13 2.2(2) . . . . ? N4 C12 C13 C14 -0.3(3) . . . . ? C12 C13 C14 C15 -1.4(2) . . . . ? C13 C14 C15 C11 1.0(2) . . . . ? N4 C11 C15 C14 1.0(2) . . . . ? C10 C11 C15 C14 -176.75(14) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.249 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.051 data_k11farm1 _database_code_depnum_ccdc_archive 'CCDC 926531' #TrackingRef 'bigcif.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H23 N3 O4' _chemical_formula_weight 417.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 6.9770(1) _cell_length_b 22.0950(2) _cell_length_c 26.6010(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4100.73(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 58101 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.093 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.893 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 56599 _diffrn_reflns_av_R_equivalents 0.0645 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4679 _reflns_number_gt 3531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski, Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick 1990)' _computing_structure_refinement 'SHELXL-97/2 (Sheldrick 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick 1997)' _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^)+(0.0350P)^2^+1.8185P] 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 4679 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0882 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 O1 O 0.86723(15) 0.19850(5) 0.71459(4) 0.0340(3) Uani 1 1 d . . . O2 O 1.36455(14) 0.04409(5) 0.66980(4) 0.0322(3) Uani 1 1 d . . . O3 O 1.22421(14) -0.01949(4) 0.59359(4) 0.0290(2) Uani 1 1 d . . . O4 O 0.87694(16) 0.00323(5) 0.55560(4) 0.0362(3) Uani 1 1 d . . . N1 N 0.63942(17) 0.20160(5) 0.65636(4) 0.0246(3) Uani 1 1 d . . . N2 N 0.54087(17) 0.18154(5) 0.61424(4) 0.0246(3) Uani 1 1 d . . . N3 N 0.09815(18) 0.23822(6) 0.56785(5) 0.0309(3) Uani 1 1 d . . . C1 C 0.8030(2) 0.17629(6) 0.67563(5) 0.0246(3) Uani 1 1 d . . . C2 C 0.9030(2) 0.12352(6) 0.65138(5) 0.0231(3) Uani 1 1 d . . . C3 C 1.0824(2) 0.10960(6) 0.67190(5) 0.0235(3) Uani 1 1 d . . . H3 H 1.1325 0.1333 0.6987 0.028 Uiso 1 1 calc R . . C4 C 1.18701(19) 0.06134(6) 0.65322(5) 0.0234(3) Uani 1 1 d . . . C5 C 1.1148(2) 0.02633(6) 0.61396(5) 0.0240(3) Uani 1 1 d . . . C6 C 0.9351(2) 0.03993(6) 0.59406(5) 0.0258(3) Uani 1 1 d . . . C7 C 0.8287(2) 0.08817(6) 0.61263(5) 0.0256(3) Uani 1 1 d . . . H7 H 0.7060 0.0970 0.5990 0.031 Uiso 1 1 calc R . . C8 C 1.4362(2) 0.07279(7) 0.71388(6) 0.0317(3) Uani 1 1 d . . . H8A H 1.4436 0.1166 0.7083 0.048 Uiso 1 1 calc R . . H8B H 1.5643 0.0571 0.7215 0.048 Uiso 1 1 calc R . . H8C H 1.3502 0.0645 0.7422 0.048 Uiso 1 1 calc R . . C9 C 1.1790(2) -0.07770(7) 0.61383(7) 0.0380(4) Uani 1 1 d . . . H9A H 1.2140 -0.0789 0.6495 0.057 Uiso 1 1 calc R . . H9B H 1.2509 -0.1089 0.5956 0.057 Uiso 1 1 calc R . . H9C H 1.0413 -0.0853 0.6103 0.057 Uiso 1 1 calc R . . C10 C 0.6969(2) 0.01707(8) 0.53283(7) 0.0413(4) Uani 1 1 d . . . H10A H 0.5941 0.0115 0.5575 0.062 Uiso 1 1 calc R . . H10B H 0.6755 -0.0100 0.5042 0.062 Uiso 1 1 calc R . . H10C H 0.6975 0.0591 0.5212 0.062 Uiso 1 1 calc R . . C11 C 0.53850(19) 0.25144(6) 0.68342(5) 0.0243(3) Uani 1 1 d . . . H11 H 0.5175 0.2400 0.7194 0.029 Uiso 1 1 calc R . . C12 C 0.3449(2) 0.25297(6) 0.65510(6) 0.0263(3) Uani 1 1 d . . . H12A H 0.2385 0.2393 0.6769 0.032 Uiso 1 1 calc R . . H12B H 0.3162 0.2941 0.6424 0.032 Uiso 1 1 calc R . . C13 C 0.3785(2) 0.20956(6) 0.61262(5) 0.0235(3) Uani 1 1 d . . . C14 C 0.2400(2) 0.19749(6) 0.57205(5) 0.0247(3) Uani 1 1 d . . . C15 C 0.2544(2) 0.14686(7) 0.54095(6) 0.0293(3) Uani 1 1 d . . . H15 H 0.3561 0.1187 0.5452 0.035 Uiso 1 1 calc R . . C16 C 0.1184(2) 0.13824(7) 0.50388(6) 0.0337(4) Uani 1 1 d . . . H16 H 0.1248 0.1040 0.4823 0.040 Uiso 1 1 calc R . . C17 C -0.0269(2) 0.18019(7) 0.49879(6) 0.0338(4) Uani 1 1 d . . . H17 H -0.1215 0.1758 0.4734 0.041 Uiso 1 1 calc R . . C18 C -0.0314(2) 0.22863(7) 0.53147(6) 0.0353(4) Uani 1 1 d . . . H18 H -0.1328 0.2570 0.5280 0.042 Uiso 1 1 calc R . . C19 C 0.6439(2) 0.31110(6) 0.68039(6) 0.0256(3) Uani 1 1 d . . . C20 C 0.7541(2) 0.32646(7) 0.63880(7) 0.0366(4) Uani 1 1 d . . . H20 H 0.7736 0.2978 0.6126 0.044 Uiso 1 1 calc R . . C21 C 0.8358(2) 0.38355(8) 0.63544(9) 0.0511(5) Uani 1 1 d . . . H21 H 0.9110 0.3938 0.6069 0.061 Uiso 1 1 calc R . . C22 C 0.8092(3) 0.42551(8) 0.67297(10) 0.0583(6) Uani 1 1 d . . . H22 H 0.8646 0.4646 0.6702 0.070 Uiso 1 1 calc R . . C23 C 0.7013(3) 0.41038(8) 0.71470(9) 0.0550(6) Uani 1 1 d . . . H23 H 0.6833 0.4391 0.7408 0.066 Uiso 1 1 calc R . . C24 C 0.6190(2) 0.35325(7) 0.71865(7) 0.0380(4) Uani 1 1 d . . . H24 H 0.5456 0.3430 0.7475 0.046 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 O1 0.0357(6) 0.0344(6) 0.0319(6) -0.0100(5) -0.0104(5) 0.0088(5) O2 0.0223(5) 0.0352(6) 0.0390(6) -0.0096(5) -0.0069(5) 0.0068(4) O3 0.0264(5) 0.0275(5) 0.0330(6) -0.0042(4) 0.0028(4) 0.0053(4) O4 0.0343(6) 0.0370(6) 0.0374(6) -0.0152(5) -0.0137(5) 0.0110(5) N1 0.0244(6) 0.0219(5) 0.0276(6) -0.0035(5) -0.0028(5) 0.0034(5) N2 0.0254(6) 0.0240(6) 0.0244(6) 0.0008(5) -0.0030(5) 0.0005(5) N3 0.0305(7) 0.0333(7) 0.0289(7) 0.0005(5) -0.0037(5) 0.0089(5) C1 0.0254(7) 0.0221(6) 0.0263(7) 0.0002(6) -0.0015(6) 0.0006(6) C2 0.0243(7) 0.0211(6) 0.0239(7) 0.0018(5) 0.0004(6) 0.0002(6) C3 0.0233(7) 0.0225(6) 0.0245(7) 0.0004(6) -0.0008(6) -0.0018(5) C4 0.0184(7) 0.0252(7) 0.0264(7) 0.0032(6) 0.0003(5) 0.0002(5) C5 0.0233(7) 0.0225(6) 0.0262(7) 0.0001(6) 0.0039(6) 0.0020(5) C6 0.0278(8) 0.0249(7) 0.0246(7) -0.0022(6) -0.0020(6) 0.0002(6) C7 0.0246(7) 0.0247(7) 0.0276(7) -0.0005(6) -0.0043(6) 0.0037(6) C8 0.0217(7) 0.0358(8) 0.0377(9) -0.0057(7) -0.0054(6) 0.0011(6) C9 0.0308(8) 0.0246(7) 0.0586(11) -0.0029(7) -0.0006(8) 0.0027(6) C10 0.0384(9) 0.0439(9) 0.0416(9) -0.0151(8) -0.0175(8) 0.0112(8) C11 0.0232(7) 0.0230(7) 0.0268(7) -0.0009(6) 0.0028(6) 0.0026(6) C12 0.0233(7) 0.0224(6) 0.0332(8) -0.0016(6) 0.0002(6) 0.0004(6) C13 0.0231(7) 0.0210(6) 0.0265(7) 0.0039(6) 0.0022(6) 0.0000(5) C14 0.0225(7) 0.0254(7) 0.0260(7) 0.0056(6) 0.0018(6) 0.0011(6) C15 0.0275(8) 0.0256(7) 0.0346(8) 0.0007(6) -0.0028(6) 0.0032(6) C16 0.0365(9) 0.0290(7) 0.0355(9) -0.0019(7) -0.0053(7) 0.0002(6) C17 0.0321(8) 0.0380(8) 0.0312(8) 0.0020(7) -0.0085(7) 0.0021(7) C18 0.0344(9) 0.0401(9) 0.0316(8) 0.0012(7) -0.0063(7) 0.0124(7) C19 0.0202(7) 0.0229(7) 0.0338(8) -0.0014(6) -0.0036(6) 0.0027(5) C20 0.0276(8) 0.0324(8) 0.0499(10) 0.0028(7) 0.0077(7) 0.0012(7) C21 0.0278(9) 0.0434(10) 0.0821(15) 0.0193(10) 0.0023(9) -0.0068(8) C22 0.0431(11) 0.0289(9) 0.1028(18) 0.0070(10) -0.0264(12) -0.0114(8) C23 0.0582(12) 0.0297(9) 0.0771(15) -0.0170(9) -0.0256(11) 0.0031(9) C24 0.0385(9) 0.0324(8) 0.0432(10) -0.0111(7) -0.0069(8) 0.0054(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 O1 C1 1.2310(17) . ? O2 C4 1.3690(17) . ? O2 C8 1.4238(18) . ? O3 C5 1.3787(16) . ? O3 C9 1.4294(18) . ? O4 C6 1.3670(17) . ? O4 C10 1.4276(19) . ? N1 C1 1.3705(18) . ? N1 N2 1.3873(16) . ? N1 C11 1.4921(17) . ? N2 C13 1.2918(18) . ? N3 C18 1.341(2) . ? N3 C14 1.3421(18) . ? C1 C2 1.5041(19) . ? C2 C7 1.393(2) . ? C2 C3 1.400(2) . ? C3 C4 1.3843(19) . ? C3 H3 0.9500 . ? C4 C5 1.394(2) . ? C5 C6 1.394(2) . ? C6 C7 1.389(2) . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C19 1.5117(19) . ? C11 C12 1.5468(19) . ? C11 H11 1.0000 . ? C12 C13 1.500(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.473(2) . ? C14 C15 1.395(2) . ? C15 C16 1.381(2) . ? C15 H15 0.9500 . ? C16 C17 1.380(2) . ? C16 H16 0.9500 . ? C17 C18 1.379(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.389(2) . ? C19 C24 1.391(2) . ? C20 C21 1.387(2) . ? C20 H20 0.9500 . ? C21 C22 1.375(3) . ? C21 H21 0.9500 . ? C22 C23 1.382(3) . ? C22 H22 0.9500 . ? C23 C24 1.391(3) . ? C23 H23 0.9500 . ? C24 H24 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 C4 O2 C8 117.34(11) . . ? C5 O3 C9 113.00(11) . . ? C6 O4 C10 116.84(11) . . ? C1 N1 N2 125.76(11) . . ? C1 N1 C11 120.92(11) . . ? N2 N1 C11 113.05(11) . . ? C13 N2 N1 107.96(11) . . ? C18 N3 C14 116.80(13) . . ? O1 C1 N1 117.08(12) . . ? O1 C1 C2 120.08(13) . . ? N1 C1 C2 122.84(12) . . ? C7 C2 C3 119.87(13) . . ? C7 C2 C1 125.41(13) . . ? C3 C2 C1 114.70(12) . . ? C4 C3 C2 120.04(13) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? O2 C4 C3 125.15(13) . . ? O2 C4 C5 114.44(12) . . ? C3 C4 C5 120.40(13) . . ? O3 C5 C4 120.14(12) . . ? O3 C5 C6 120.46(13) . . ? C4 C5 C6 119.33(12) . . ? O4 C6 C7 124.25(13) . . ? O4 C6 C5 115.03(12) . . ? C7 C6 C5 120.71(13) . . ? C6 C7 C2 119.63(13) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O3 C9 H9A 109.5 . . ? O3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O4 C10 H10A 109.5 . . ? O4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C19 112.84(11) . . ? N1 C11 C12 101.14(11) . . ? C19 C11 C12 112.32(11) . . ? N1 C11 H11 110.1 . . ? C19 C11 H11 110.1 . . ? C12 C11 H11 110.1 . . ? C13 C12 C11 102.50(11) . . ? C13 C12 H12A 111.3 . . ? C11 C12 H12A 111.3 . . ? C13 C12 H12B 111.3 . . ? C11 C12 H12B 111.3 . . ? H12A C12 H12B 109.2 . . ? N2 C13 C14 120.86(13) . . ? N2 C13 C12 114.72(12) . . ? C14 C13 C12 124.40(12) . . ? N3 C14 C15 122.79(13) . . ? N3 C14 C13 115.03(13) . . ? C15 C14 C13 122.17(13) . . ? C16 C15 C14 118.97(14) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C17 C16 C15 118.79(14) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C18 C17 C16 118.43(14) . . ? C18 C17 H17 120.8 . . ? C16 C17 H17 120.8 . . ? N3 C18 C17 124.20(14) . . ? N3 C18 H18 117.9 . . ? C17 C18 H18 117.9 . . ? C20 C19 C24 119.25(14) . . ? C20 C19 C11 121.66(13) . . ? C24 C19 C11 118.94(14) . . ? C21 C20 C19 120.06(17) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C22 C21 C20 120.71(19) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C23 119.58(17) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C22 C23 C24 120.34(18) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C19 C24 C23 120.05(18) . . ? C19 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C13 169.20(13) . . . . ? C11 N1 N2 C13 -4.79(15) . . . . ? N2 N1 C1 O1 -177.09(13) . . . . ? C11 N1 C1 O1 -3.5(2) . . . . ? N2 N1 C1 C2 2.6(2) . . . . ? C11 N1 C1 C2 176.19(12) . . . . ? O1 C1 C2 C7 168.54(14) . . . . ? N1 C1 C2 C7 -11.2(2) . . . . ? O1 C1 C2 C3 -9.42(19) . . . . ? N1 C1 C2 C3 170.87(13) . . . . ? C7 C2 C3 C4 0.9(2) . . . . ? C1 C2 C3 C4 179.01(12) . . . . ? C8 O2 C4 C3 8.8(2) . . . . ? C8 O2 C4 C5 -172.17(12) . . . . ? C2 C3 C4 O2 179.03(13) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C9 O3 C5 C4 97.25(16) . . . . ? C9 O3 C5 C6 -85.70(16) . . . . ? O2 C4 C5 O3 -2.82(19) . . . . ? C3 C4 C5 O3 176.28(12) . . . . ? O2 C4 C5 C6 -179.90(12) . . . . ? C3 C4 C5 C6 -0.8(2) . . . . ? C10 O4 C6 C7 1.5(2) . . . . ? C10 O4 C6 C5 -177.62(14) . . . . ? O3 C5 C6 O4 2.7(2) . . . . ? C4 C5 C6 O4 179.79(13) . . . . ? O3 C5 C6 C7 -176.46(13) . . . . ? C4 C5 C6 C7 0.6(2) . . . . ? O4 C6 C7 C2 -178.76(14) . . . . ? C5 C6 C7 C2 0.3(2) . . . . ? C3 C2 C7 C6 -1.1(2) . . . . ? C1 C2 C7 C6 -178.97(13) . . . . ? C1 N1 C11 C19 73.16(16) . . . . ? N2 N1 C11 C19 -112.52(13) . . . . ? C1 N1 C11 C12 -166.64(12) . . . . ? N2 N1 C11 C12 7.68(14) . . . . ? N1 C11 C12 C13 -7.14(13) . . . . ? C19 C11 C12 C13 113.43(13) . . . . ? N1 N2 C13 C14 -179.52(12) . . . . ? N1 N2 C13 C12 -0.65(16) . . . . ? C11 C12 C13 N2 5.34(16) . . . . ? C11 C12 C13 C14 -175.84(12) . . . . ? C18 N3 C14 C15 -0.7(2) . . . . ? C18 N3 C14 C13 -179.71(13) . . . . ? N2 C13 C14 N3 -165.69(13) . . . . ? C12 C13 C14 N3 15.6(2) . . . . ? N2 C13 C14 C15 15.3(2) . . . . ? C12 C13 C14 C15 -163.49(14) . . . . ? N3 C14 C15 C16 0.6(2) . . . . ? C13 C14 C15 C16 179.55(14) . . . . ? C14 C15 C16 C17 0.2(2) . . . . ? C15 C16 C17 C18 -0.8(2) . . . . ? C14 N3 C18 C17 0.0(2) . . . . ? C16 C17 C18 N3 0.8(3) . . . . ? N1 C11 C19 C20 31.53(19) . . . . ? C12 C11 C19 C20 -82.02(17) . . . . ? N1 C11 C19 C24 -153.00(13) . . . . ? C12 C11 C19 C24 93.45(16) . . . . ? C24 C19 C20 C21 -0.8(2) . . . . ? C11 C19 C20 C21 174.63(15) . . . . ? C19 C20 C21 C22 0.0(3) . . . . ? C20 C21 C22 C23 0.6(3) . . . . ? C21 C22 C23 C24 -0.4(3) . . . . ? C20 C19 C24 C23 1.0(2) . . . . ? C11 C19 C24 C23 -174.57(15) . . . . ? C22 C23 C24 C19 -0.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.182 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.042