# Electronic Supplementary Material (ESI) for RSC Advances # 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_global data_ss005 #TrackingRef 'ss005.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 N O3 S' _chemical_formula_weight 285.31 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 12.6212(3) _cell_length_b 6.9825(2) _cell_length_c 15.3469(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.991(3) _cell_angle_gamma 90.00 _cell_volume 1322.97(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5623 _cell_measurement_theta_min 2.9137 _cell_measurement_theta_max 32.4100 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.250 _exptl_absorpt_correction_T_min 0.9446 _exptl_absorpt_correction_T_max 0.9682 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Micro-Focus (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8823 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2319 _reflns_number_gt 2075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0397P)^2^+0.7603P] 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 RIDING _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2319 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 -0.18591(3) 0.22510(7) 0.45538(3) 0.03002(15) Uani 1 1 d . . . O1 O -0.18432(10) 0.3980(2) 0.50441(8) 0.0406(3) Uani 1 1 d . . . O2 O -0.17059(10) 0.0502(2) 0.50332(8) 0.0403(3) Uani 1 1 d . . . O3 O -0.09644(9) 0.24262(18) 0.39415(7) 0.0311(3) Uani 1 1 d . . . N1 N -0.29389(11) 0.2155(2) 0.37456(9) 0.0292(3) Uani 1 1 d . . . C1 C -0.26498(13) 0.2205(2) 0.29791(11) 0.0235(4) Uani 1 1 d . . . C2 C -0.14811(13) 0.2308(2) 0.30381(10) 0.0221(3) Uani 1 1 d . . . C3 C -0.09034(12) 0.2222(2) 0.23947(10) 0.0219(3) Uani 1 1 d . . . H3 H -0.1319 0.2083 0.1807 0.026 Uiso 1 1 calc R . . C4 C 0.02665(12) 0.2312(2) 0.24657(11) 0.0228(3) Uani 1 1 d . . . C5 C 0.10253(13) 0.2578(2) 0.32716(12) 0.0270(4) Uani 1 1 d . . . H5 H 0.0787 0.2696 0.3817 0.032 Uiso 1 1 calc R . . C6 C 0.21170(14) 0.2668(2) 0.32631(13) 0.0320(4) Uani 1 1 d . . . H6 H 0.2624 0.2864 0.3806 0.038 Uiso 1 1 calc R . . C7 C 0.24854(14) 0.2479(2) 0.24799(13) 0.0325(4) Uani 1 1 d . . . H7 H 0.3240 0.2522 0.2489 0.039 Uiso 1 1 calc R . . C8 C 0.17541(14) 0.2228(2) 0.16854(13) 0.0318(4) Uani 1 1 d . . . H8 H 0.2004 0.2113 0.1145 0.038 Uiso 1 1 calc R . . C9 C 0.06540(13) 0.2145(2) 0.16759(11) 0.0276(4) Uani 1 1 d . . . H9 H 0.0155 0.1972 0.1126 0.033 Uiso 1 1 calc R . . C10 C -0.34946(12) 0.2150(2) 0.21526(11) 0.0231(3) Uani 1 1 d . . . C11 C -0.33907(13) 0.3127(2) 0.13906(11) 0.0265(4) Uani 1 1 d . . . H11 H -0.2751 0.3839 0.1382 0.032 Uiso 1 1 calc R . . C12 C -0.42161(14) 0.3070(3) 0.06410(12) 0.0341(4) Uani 1 1 d . . . H12 H -0.4145 0.3754 0.0121 0.041 Uiso 1 1 calc R . . C13 C -0.51476(15) 0.2017(3) 0.06450(13) 0.0416(5) Uani 1 1 d . . . H13 H -0.5709 0.1967 0.0127 0.050 Uiso 1 1 calc R . . C14 C -0.52564(13) 0.1035(3) 0.14102(13) 0.0377(4) Uani 1 1 d . . . H14 H -0.5893 0.0312 0.1415 0.045 Uiso 1 1 calc R . . C15 C -0.44393(13) 0.1114(2) 0.21606(12) 0.0298(4) Uani 1 1 d . . . H15 H -0.4519 0.0459 0.2686 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0328(3) 0.0399(3) 0.0179(2) 0.00165(17) 0.00643(18) 0.00337(18) O1 0.0493(8) 0.0474(8) 0.0261(6) -0.0074(6) 0.0099(6) 0.0019(6) O2 0.0466(7) 0.0484(8) 0.0270(6) 0.0123(6) 0.0097(6) 0.0077(6) O3 0.0269(6) 0.0481(8) 0.0179(6) -0.0006(5) 0.0036(5) -0.0001(5) N1 0.0299(8) 0.0352(8) 0.0228(7) 0.0023(6) 0.0065(6) 0.0029(6) C1 0.0257(8) 0.0206(8) 0.0248(8) -0.0002(6) 0.0068(7) 0.0020(6) C2 0.0257(8) 0.0216(8) 0.0174(8) 0.0010(6) 0.0005(6) -0.0003(6) C3 0.0228(8) 0.0213(8) 0.0200(8) -0.0003(6) 0.0013(6) 0.0004(6) C4 0.0208(8) 0.0172(8) 0.0299(9) 0.0021(6) 0.0039(7) 0.0007(6) C5 0.0258(8) 0.0264(9) 0.0276(9) 0.0010(7) 0.0027(7) 0.0013(6) C6 0.0223(8) 0.0290(9) 0.0408(10) -0.0022(7) -0.0027(7) 0.0007(7) C7 0.0220(8) 0.0236(9) 0.0529(12) 0.0003(8) 0.0098(8) 0.0003(7) C8 0.0305(9) 0.0275(9) 0.0415(10) 0.0013(7) 0.0172(8) 0.0004(7) C9 0.0286(9) 0.0273(9) 0.0265(9) 0.0011(7) 0.0046(7) 0.0011(7) C10 0.0195(7) 0.0229(8) 0.0269(8) -0.0037(6) 0.0048(6) 0.0029(6) C11 0.0233(8) 0.0293(9) 0.0264(8) -0.0019(7) 0.0039(7) 0.0027(7) C12 0.0309(9) 0.0447(11) 0.0256(9) 0.0014(8) 0.0037(7) 0.0080(8) C13 0.0262(9) 0.0561(13) 0.0364(10) -0.0127(9) -0.0073(8) 0.0065(9) C14 0.0203(8) 0.0382(10) 0.0533(12) -0.0105(9) 0.0045(8) -0.0045(7) C15 0.0254(8) 0.0295(9) 0.0354(9) -0.0005(7) 0.0084(7) 0.0017(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 S1 O2 1.4180(13) . ? S1 O1 1.4205(13) . ? S1 O3 1.6168(12) . ? S1 N1 1.6425(14) . ? O3 C2 1.4067(19) . ? N1 C1 1.302(2) . ? C1 C2 1.461(2) . ? C1 C10 1.478(2) . ? C2 C3 1.345(2) . ? C3 C4 1.459(2) . ? C3 H3 0.9500 . ? C4 C9 1.403(2) . ? C4 C5 1.410(2) . ? C5 C6 1.382(2) . ? C5 H5 0.9500 . ? C6 C7 1.382(3) . ? C6 H6 0.9500 . ? C7 C8 1.379(3) . ? C7 H7 0.9500 . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.383(2) . ? C10 C15 1.397(2) . ? C11 C12 1.383(2) . ? C11 H11 0.9500 . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 C14 1.391(3) . ? C13 H13 0.9500 . ? C14 C15 1.378(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 O2 S1 O1 118.13(8) . . ? O2 S1 O3 109.29(7) . . ? O1 S1 O3 107.99(7) . . ? O2 S1 N1 111.05(8) . . ? O1 S1 N1 110.66(8) . . ? O3 S1 N1 97.72(6) . . ? C2 O3 S1 109.36(10) . . ? C1 N1 S1 109.68(12) . . ? N1 C1 C2 114.47(14) . . ? N1 C1 C10 119.14(14) . . ? C2 C1 C10 126.40(14) . . ? C3 C2 O3 121.00(14) . . ? C3 C2 C1 130.30(14) . . ? O3 C2 C1 108.63(13) . . ? C2 C3 C4 129.62(15) . . ? C2 C3 H3 115.2 . . ? C4 C3 H3 115.2 . . ? C9 C4 C5 118.26(15) . . ? C9 C4 C3 117.45(15) . . ? C5 C4 C3 124.29(15) . . ? C6 C5 C4 119.63(16) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 121.34(17) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 119.78(16) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 119.97(17) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C4 121.02(16) . . ? C8 C9 H9 119.5 . . ? C4 C9 H9 119.5 . . ? C11 C10 C15 119.60(15) . . ? C11 C10 C1 122.31(14) . . ? C15 C10 C1 118.06(15) . . ? C12 C11 C10 120.11(16) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.27(17) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 119.82(16) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 119.86(16) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C10 120.33(17) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? 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 O2 S1 O3 C2 112.21(11) . . . . ? O1 S1 O3 C2 -118.08(11) . . . . ? N1 S1 O3 C2 -3.35(11) . . . . ? O2 S1 N1 C1 -112.55(12) . . . . ? O1 S1 N1 C1 114.21(12) . . . . ? O3 S1 N1 C1 1.62(13) . . . . ? S1 N1 C1 C2 0.62(17) . . . . ? S1 N1 C1 C10 -179.52(11) . . . . ? S1 O3 C2 C3 -173.26(12) . . . . ? S1 O3 C2 C1 3.97(15) . . . . ? N1 C1 C2 C3 173.87(16) . . . . ? C10 C1 C2 C3 -6.0(3) . . . . ? N1 C1 C2 O3 -3.01(19) . . . . ? C10 C1 C2 O3 177.15(14) . . . . ? O3 C2 C3 C4 -2.9(3) . . . . ? C1 C2 C3 C4 -179.45(15) . . . . ? C2 C3 C4 C9 178.69(16) . . . . ? C2 C3 C4 C5 -2.2(3) . . . . ? C9 C4 C5 C6 0.0(2) . . . . ? C3 C4 C5 C6 -179.12(15) . . . . ? C4 C5 C6 C7 -0.8(3) . . . . ? C5 C6 C7 C8 1.1(3) . . . . ? C6 C7 C8 C9 -0.7(2) . . . . ? C7 C8 C9 C4 0.0(2) . . . . ? C5 C4 C9 C8 0.4(2) . . . . ? C3 C4 C9 C8 179.56(15) . . . . ? N1 C1 C10 C11 145.70(16) . . . . ? C2 C1 C10 C11 -34.5(2) . . . . ? N1 C1 C10 C15 -32.4(2) . . . . ? C2 C1 C10 C15 147.40(16) . . . . ? C15 C10 C11 C12 -0.3(2) . . . . ? C1 C10 C11 C12 -178.36(15) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? C13 C14 C15 C10 -1.0(3) . . . . ? C11 C10 C15 C14 1.1(2) . . . . ? C1 C10 C15 C14 179.29(15) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.164 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 913688' ####################################################################### # # 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_global # Attachment 'ss008.cif' data_ss008 #TrackingRef 'ss008.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 N O5 S' _chemical_formula_weight 403.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P 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 9.8446(3) _cell_length_b 14.2440(3) _cell_length_c 15.0095(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.378(2) _cell_angle_gamma 90.00 _cell_volume 2087.30(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8473 _cell_measurement_theta_min 2.9947 _cell_measurement_theta_max 32.4927 _exptl_crystal_description block _exptl_crystal_colour color _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.186 _exptl_absorpt_correction_T_min 0.9584 _exptl_absorpt_correction_T_max 0.9780 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Micro-Focus (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17195 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3671 _reflns_number_gt 3227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0469P)^2^+0.8205P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3671 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.42388(5) 0.06443(3) 0.36008(3) 0.04210(15) Uani 1 1 d . . . O3 O 0.47095(15) 0.10415(10) 0.28320(9) 0.0542(4) Uani 1 1 d . . . O1 O 0.26394(13) 0.05704(9) 0.34051(8) 0.0454(3) Uani 1 1 d . . . O2 O 0.48108(15) -0.02139(9) 0.39357(9) 0.0561(4) Uani 1 1 d . . . O4 O 0.64781(15) 0.16834(11) 0.45506(11) 0.0638(4) Uani 1 1 d . . . O5 O 0.50798(15) 0.25061(9) 0.53656(9) 0.0535(4) Uani 1 1 d . . . N1 N 0.41870(16) 0.14205(10) 0.44167(10) 0.0434(4) Uani 1 1 d . . . C1 C 0.2035(2) 0.07052(12) 0.42504(12) 0.0435(4) Uani 1 1 d . . . H1 H 0.2224 0.0154 0.4637 0.052 Uiso 1 1 calc R . . C2 C 0.2819(2) 0.15615(12) 0.46868(12) 0.0423(4) Uani 1 1 d . . . H2 H 0.2880 0.1507 0.5342 0.051 Uiso 1 1 calc R . . C3 C 0.5383(2) 0.18700(13) 0.47769(13) 0.0471(5) Uani 1 1 d . . . C4 C 0.6055(2) 0.32718(14) 0.56684(14) 0.0570(5) Uani 1 1 d . . . C5 C 0.5262(3) 0.38277(19) 0.6284(2) 0.0895(9) Uani 1 1 d . . . H5A H 0.5078 0.3439 0.6777 0.134 Uiso 1 1 calc R . . H5B H 0.4412 0.4035 0.5957 0.134 Uiso 1 1 calc R . . H5C H 0.5790 0.4363 0.6510 0.134 Uiso 1 1 calc R . . C6 C 0.6297(3) 0.38418(19) 0.48562(19) 0.0883(9) Uani 1 1 d . . . H6A H 0.5433 0.4008 0.4522 0.132 Uiso 1 1 calc R . . H6B H 0.6819 0.3478 0.4483 0.132 Uiso 1 1 calc R . . H6C H 0.6794 0.4402 0.5047 0.132 Uiso 1 1 calc R . . C7 C 0.7362(3) 0.2878(2) 0.6145(2) 0.0992(11) Uani 1 1 d . . . H7A H 0.7155 0.2431 0.6587 0.149 Uiso 1 1 calc R . . H7B H 0.7905 0.3377 0.6435 0.149 Uiso 1 1 calc R . . H7C H 0.7862 0.2574 0.5718 0.149 Uiso 1 1 calc R . . C14 C 0.0515(2) 0.08189(13) 0.40117(14) 0.0501(5) Uani 1 1 d . . . H14A H 0.0355 0.1348 0.3604 0.060 Uiso 1 1 calc R . . H14B H 0.0129 0.0980 0.4555 0.060 Uiso 1 1 calc R . . C15 C -0.02628(19) -0.00146(13) 0.35848(13) 0.0447(4) Uani 1 1 d . . . C16 C 0.0330(2) -0.08664(14) 0.34170(16) 0.0581(5) Uani 1 1 d . . . H16 H 0.1267 -0.0949 0.3574 0.070 Uiso 1 1 calc R . . C17 C -0.0452(2) -0.15982(14) 0.30187(16) 0.0590(6) Uani 1 1 d . . . H17 H -0.0027 -0.2164 0.2916 0.071 Uiso 1 1 calc R . . C18 C -0.1841(2) -0.15104(14) 0.27703(14) 0.0525(5) Uani 1 1 d . . . C19 C -0.2428(2) -0.06619(16) 0.29413(16) 0.0602(6) Uani 1 1 d . . . H19 H -0.3366 -0.0581 0.2783 0.072 Uiso 1 1 calc R . . C20 C -0.1660(2) 0.00716(15) 0.33419(14) 0.0554(5) Uani 1 1 d . . . H20 H -0.2090 0.0634 0.3450 0.066 Uiso 1 1 calc R . . C21 C -0.2692(3) -0.23155(18) 0.23599(19) 0.0766(7) Uani 1 1 d . . . H21A H -0.2238 -0.2603 0.1901 0.115 Uiso 1 1 calc R . . H21B H -0.3572 -0.2087 0.2101 0.115 Uiso 1 1 calc R . . H21C H -0.2809 -0.2770 0.2816 0.115 Uiso 1 1 calc R . . C22 C 0.22138(19) 0.25093(12) 0.44019(12) 0.0424(4) Uani 1 1 d . . . C23 C 0.2499(2) 0.29554(15) 0.36322(14) 0.0578(5) Uani 1 1 d . . . H23 H 0.3108 0.2684 0.3283 0.069 Uiso 1 1 calc R . . C24 C 0.1888(3) 0.38025(17) 0.33758(17) 0.0734(7) Uani 1 1 d . . . H24 H 0.2092 0.4096 0.2855 0.088 Uiso 1 1 calc R . . C25 C 0.0994(3) 0.42133(16) 0.38734(19) 0.0731(7) Uani 1 1 d . . . H25 H 0.0580 0.4781 0.3694 0.088 Uiso 1 1 calc R . . C26 C 0.0707(3) 0.37801(17) 0.4646(2) 0.0777(7) Uani 1 1 d . . . H26 H 0.0097 0.4056 0.4992 0.093 Uiso 1 1 calc R . . C27 C 0.1321(3) 0.29362(15) 0.49102(16) 0.0627(6) Uani 1 1 d . . . H27 H 0.1130 0.2653 0.5438 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 S1 0.0478(3) 0.0371(3) 0.0408(3) -0.00287(18) 0.00347(19) 0.00293(18) O3 0.0593(9) 0.0576(8) 0.0472(7) 0.0006(6) 0.0124(6) -0.0042(7) O1 0.0465(8) 0.0479(7) 0.0414(7) -0.0083(5) 0.0042(6) -0.0020(6) O2 0.0679(10) 0.0412(7) 0.0586(8) -0.0009(6) 0.0057(7) 0.0141(6) O4 0.0510(9) 0.0611(9) 0.0777(10) -0.0163(8) 0.0019(8) 0.0018(7) O5 0.0601(9) 0.0451(7) 0.0536(8) -0.0125(6) 0.0006(7) -0.0033(6) N1 0.0468(9) 0.0385(8) 0.0431(8) -0.0061(6) -0.0007(7) 0.0044(7) C1 0.0535(11) 0.0373(9) 0.0407(9) 0.0019(7) 0.0102(8) 0.0026(8) C2 0.0532(11) 0.0395(10) 0.0341(9) 0.0006(7) 0.0052(8) 0.0031(8) C3 0.0526(12) 0.0394(10) 0.0469(10) -0.0006(8) -0.0033(9) 0.0026(8) C4 0.0676(14) 0.0436(11) 0.0547(12) -0.0076(9) -0.0113(10) -0.0055(9) C5 0.111(2) 0.0698(17) 0.0888(19) -0.0358(15) 0.0178(17) -0.0164(15) C6 0.121(3) 0.0589(15) 0.0849(18) 0.0024(14) 0.0120(17) -0.0179(15) C7 0.095(2) 0.087(2) 0.101(2) -0.0144(17) -0.0470(18) 0.0023(16) C14 0.0526(12) 0.0387(10) 0.0602(12) -0.0014(8) 0.0120(9) 0.0030(8) C15 0.0466(11) 0.0387(9) 0.0506(10) 0.0020(8) 0.0136(8) 0.0023(8) C16 0.0427(11) 0.0451(11) 0.0881(16) -0.0064(11) 0.0140(10) 0.0026(9) C17 0.0531(12) 0.0406(11) 0.0860(15) -0.0105(10) 0.0193(11) 0.0010(9) C18 0.0522(12) 0.0520(12) 0.0553(11) -0.0036(9) 0.0152(9) -0.0064(9) C19 0.0438(11) 0.0646(14) 0.0717(14) -0.0074(11) 0.0051(10) 0.0041(10) C20 0.0509(12) 0.0482(11) 0.0675(13) -0.0040(10) 0.0091(10) 0.0108(9) C21 0.0704(16) 0.0706(16) 0.0902(18) -0.0165(14) 0.0157(14) -0.0187(13) C22 0.0491(11) 0.0355(9) 0.0420(9) -0.0041(7) 0.0039(8) 0.0012(8) C23 0.0755(15) 0.0518(12) 0.0470(11) 0.0081(9) 0.0120(10) 0.0151(10) C24 0.102(2) 0.0557(14) 0.0625(14) 0.0159(11) 0.0090(13) 0.0160(13) C25 0.0839(18) 0.0435(12) 0.0885(18) 0.0029(12) -0.0017(14) 0.0168(11) C26 0.0834(18) 0.0523(14) 0.102(2) -0.0126(13) 0.0289(15) 0.0199(12) C27 0.0805(16) 0.0466(12) 0.0659(13) -0.0031(10) 0.0281(12) 0.0071(11) _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 O2 1.4111(14) . ? S1 O3 1.4155(14) . ? S1 O1 1.5677(14) . ? S1 N1 1.6555(15) . ? O1 C1 1.482(2) . ? O4 C3 1.201(2) . ? O5 C3 1.326(2) . ? O5 C4 1.485(2) . ? N1 C3 1.387(2) . ? N1 C2 1.469(2) . ? C1 C14 1.502(3) . ? C1 C2 1.544(3) . ? C1 H1 0.9800 . ? C2 C22 1.515(2) . ? C2 H2 0.9800 . ? C4 C7 1.498(3) . ? C4 C5 1.509(3) . ? C4 C6 1.509(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C14 C15 1.510(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C20 1.382(3) . ? C15 C16 1.383(3) . ? C16 C17 1.385(3) . ? C16 H16 0.9300 . ? C17 C18 1.376(3) . ? C17 H17 0.9300 . ? C18 C19 1.378(3) . ? C18 C21 1.505(3) . ? C19 C20 1.382(3) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C27 1.377(3) . ? C22 C23 1.379(3) . ? C23 C24 1.381(3) . ? C23 H23 0.9300 . ? C24 C25 1.358(4) . ? C24 H24 0.9300 . ? C25 C26 1.374(4) . ? C25 H25 0.9300 . ? C26 C27 1.381(3) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O3 118.63(9) . . ? O2 S1 O1 110.72(8) . . ? O3 S1 O1 107.47(8) . . ? O2 S1 N1 111.33(8) . . ? O3 S1 N1 112.36(8) . . ? O1 S1 N1 93.32(7) . . ? C1 O1 S1 109.59(11) . . ? C3 O5 C4 120.93(17) . . ? C3 N1 C2 126.25(15) . . ? C3 N1 S1 119.43(13) . . ? C2 N1 S1 114.32(12) . . ? O1 C1 C14 107.89(15) . . ? O1 C1 C2 103.39(14) . . ? C14 C1 C2 116.41(15) . . ? O1 C1 H1 109.6 . . ? C14 C1 H1 109.6 . . ? C2 C1 H1 109.6 . . ? N1 C2 C22 112.66(15) . . ? N1 C2 C1 101.61(14) . . ? C22 C2 C1 115.27(15) . . ? N1 C2 H2 109.0 . . ? C22 C2 H2 109.0 . . ? C1 C2 H2 109.0 . . ? O4 C3 O5 128.80(19) . . ? O4 C3 N1 122.36(18) . . ? O5 C3 N1 108.83(17) . . ? O5 C4 C7 110.66(18) . . ? O5 C4 C5 102.01(19) . . ? C7 C4 C5 112.6(2) . . ? O5 C4 C6 108.11(17) . . ? C7 C4 C6 111.8(3) . . ? C5 C4 C6 111.1(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 C14 C15 116.85(16) . . ? C1 C14 H14A 108.1 . . ? C15 C14 H14A 108.1 . . ? C1 C14 H14B 108.1 . . ? C15 C14 H14B 108.1 . . ? H14A C14 H14B 107.3 . . ? C20 C15 C16 117.28(18) . . ? C20 C15 C14 118.37(17) . . ? C16 C15 C14 124.35(18) . . ? C15 C16 C17 121.0(2) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C18 C17 C16 121.75(19) . . ? C18 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C17 C18 C19 117.10(19) . . ? C17 C18 C21 121.6(2) . . ? C19 C18 C21 121.3(2) . . ? C18 C19 C20 121.6(2) . . ? C18 C19 H19 119.2 . . ? C20 C19 H19 119.2 . . ? C19 C20 C15 121.22(19) . . ? C19 C20 H20 119.4 . . ? C15 C20 H20 119.4 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C27 C22 C23 118.28(19) . . ? C27 C22 C2 119.54(17) . . ? C23 C22 C2 122.16(17) . . ? C22 C23 C24 120.5(2) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C25 C24 C23 120.9(2) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C24 C25 C26 119.2(2) . . ? C24 C25 H25 120.4 . . ? C26 C25 H25 120.4 . . ? C25 C26 C27 120.2(2) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C22 C27 C26 120.8(2) . . ? C22 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? 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 O2 S1 O1 C1 81.81(12) . . . . ? O3 S1 O1 C1 -147.18(11) . . . . ? N1 S1 O1 C1 -32.49(12) . . . . ? O2 S1 N1 C3 75.90(16) . . . . ? O3 S1 N1 C3 -59.90(16) . . . . ? O1 S1 N1 C3 -170.32(14) . . . . ? O2 S1 N1 C2 -104.21(13) . . . . ? O3 S1 N1 C2 119.99(13) . . . . ? O1 S1 N1 C2 9.57(13) . . . . ? S1 O1 C1 C14 169.07(12) . . . . ? S1 O1 C1 C2 45.19(15) . . . . ? C3 N1 C2 C22 70.7(2) . . . . ? S1 N1 C2 C22 -109.16(14) . . . . ? C3 N1 C2 C1 -165.35(16) . . . . ? S1 N1 C2 C1 14.77(16) . . . . ? O1 C1 C2 N1 -34.64(16) . . . . ? C14 C1 C2 N1 -152.73(16) . . . . ? O1 C1 C2 C22 87.50(18) . . . . ? C14 C1 C2 C22 -30.6(2) . . . . ? C4 O5 C3 O4 16.4(3) . . . . ? C4 O5 C3 N1 -162.68(15) . . . . ? C2 N1 C3 O4 176.25(18) . . . . ? S1 N1 C3 O4 -3.9(3) . . . . ? C2 N1 C3 O5 -4.6(2) . . . . ? S1 N1 C3 O5 175.29(12) . . . . ? C3 O5 C4 C7 -62.4(3) . . . . ? C3 O5 C4 C5 177.60(19) . . . . ? C3 O5 C4 C6 60.4(2) . . . . ? O1 C1 C14 C15 64.4(2) . . . . ? C2 C1 C14 C15 -179.97(16) . . . . ? C1 C14 C15 C20 -178.87(18) . . . . ? C1 C14 C15 C16 1.1(3) . . . . ? C20 C15 C16 C17 0.2(3) . . . . ? C14 C15 C16 C17 -179.7(2) . . . . ? C15 C16 C17 C18 0.3(4) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? C16 C17 C18 C21 -178.4(2) . . . . ? C17 C18 C19 C20 0.2(3) . . . . ? C21 C18 C19 C20 178.1(2) . . . . ? C18 C19 C20 C15 0.3(4) . . . . ? C16 C15 C20 C19 -0.5(3) . . . . ? C14 C15 C20 C19 179.4(2) . . . . ? N1 C2 C22 C27 -150.12(19) . . . . ? C1 C2 C22 C27 93.9(2) . . . . ? N1 C2 C22 C23 31.5(2) . . . . ? C1 C2 C22 C23 -84.4(2) . . . . ? C27 C22 C23 C24 -0.8(3) . . . . ? C2 C22 C23 C24 177.6(2) . . . . ? C22 C23 C24 C25 -0.1(4) . . . . ? C23 C24 C25 C26 0.6(4) . . . . ? C24 C25 C26 C27 -0.1(4) . . . . ? C23 C22 C27 C26 1.3(3) . . . . ? C2 C22 C27 C26 -177.1(2) . . . . ? C25 C26 C27 C22 -0.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.262 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 913689' ####################################################################### # # 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_global # Attachment 'ss009.cif' data_ss009 #TrackingRef 'ss009.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 N4 O2' _chemical_formula_weight 364.44 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 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 5.47870(10) _cell_length_b 21.0779(6) _cell_length_c 16.8942(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.526(2) _cell_angle_gamma 90.00 _cell_volume 1947.24(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4354 _cell_measurement_theta_min 3.0879 _cell_measurement_theta_max 32.5803 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_min 0.9935 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Micro-Focus (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13935 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3431 _reflns_number_gt 2786 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0640P)^2^+1.1608P] 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 RIDING _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3431 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1427 _refine_ls_wR_factor_gt 0.1321 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 N1 N 0.1724(3) 0.68203(9) 0.24195(10) 0.0276(4) Uani 1 1 d . . . N2 N 0.0622(3) 0.65294(9) 0.18752(11) 0.0282(4) Uani 1 1 d . . . N3 N -0.0600(4) 0.62662(10) 0.14178(13) 0.0406(5) Uani 1 1 d . . . N4 N 0.4553(3) 0.80471(8) 0.24609(10) 0.0267(4) Uani 1 1 d . . . H4 H 0.3074 0.8137 0.2563 0.032 Uiso 1 1 calc R . . O1 O 0.8563(3) 0.83036(7) 0.27111(9) 0.0344(4) Uani 1 1 d . . . O2 O 0.5502(3) 0.89016(7) 0.31711(9) 0.0291(4) Uani 1 1 d . . . C1 C 0.4425(3) 0.68683(10) 0.23445(12) 0.0233(5) Uani 1 1 d . . . H1 H 0.4929 0.6525 0.1998 0.028 Uiso 1 1 calc R . . C2 C 0.5680(4) 0.67706(11) 0.31690(12) 0.0279(5) Uani 1 1 d . . . C3 C 0.5231(4) 0.61078(10) 0.34732(12) 0.0251(5) Uani 1 1 d . . . C4 C 0.3186(4) 0.59752(10) 0.38913(12) 0.0285(5) Uani 1 1 d . . . H4A H 0.2121 0.6302 0.4006 0.034 Uiso 1 1 calc R . . C5 C 0.2709(4) 0.53641(11) 0.41406(12) 0.0295(5) Uani 1 1 d . . . H5 H 0.1333 0.5289 0.4423 0.035 Uiso 1 1 calc R . . C6 C 0.4224(4) 0.48633(10) 0.39809(12) 0.0280(5) Uani 1 1 d . . . C7 C 0.3595(5) 0.41981(11) 0.42186(14) 0.0382(6) Uani 1 1 d . . . H7A H 0.2894 0.4206 0.4725 0.057 Uiso 1 1 calc R . . H7B H 0.5051 0.3944 0.4252 0.057 Uiso 1 1 calc R . . H7C H 0.2439 0.4020 0.3830 0.057 Uiso 1 1 calc R . . C8 C 0.6287(4) 0.49949(11) 0.35743(13) 0.0317(5) Uani 1 1 d . . . H8 H 0.7358 0.4668 0.3467 0.038 Uiso 1 1 calc R . . C9 C 0.6781(4) 0.56076(11) 0.33233(13) 0.0304(5) Uani 1 1 d . . . H9 H 0.8175 0.5683 0.3050 0.037 Uiso 1 1 calc R . . C10 C 0.5012(4) 0.75097(9) 0.19547(12) 0.0244(5) Uani 1 1 d . . . H10 H 0.6766 0.7509 0.1871 0.029 Uiso 1 1 calc R . . C11 C 0.3676(4) 0.75468(9) 0.11428(12) 0.0237(5) Uani 1 1 d . . . C12 C 0.4541(4) 0.71818(10) 0.05260(12) 0.0274(5) Uani 1 1 d . . . H12 H 0.5995 0.6957 0.0610 0.033 Uiso 1 1 calc R . . C13 C 0.3273(4) 0.71497(11) -0.02031(13) 0.0314(5) Uani 1 1 d . . . H13 H 0.3868 0.6902 -0.0604 0.038 Uiso 1 1 calc R . . C14 C 0.1120(4) 0.74851(11) -0.03409(13) 0.0316(5) Uani 1 1 d . . . H14 H 0.0264 0.7464 -0.0833 0.038 Uiso 1 1 calc R . . C15 C 0.0250(4) 0.78523(10) 0.02575(13) 0.0300(5) Uani 1 1 d . . . H15 H -0.1192 0.8080 0.0165 0.036 Uiso 1 1 calc R . . C16 C 0.1508(4) 0.78840(10) 0.09956(13) 0.0274(5) Uani 1 1 d . . . H16 H 0.0900 0.8132 0.1394 0.033 Uiso 1 1 calc R . . C17 C 0.6410(4) 0.84121(10) 0.27774(12) 0.0262(5) Uani 1 1 d . . . C18 C 0.7139(4) 0.93825(10) 0.35696(12) 0.0273(5) Uani 1 1 d . . . C19 C 0.5327(5) 0.98661(13) 0.38415(17) 0.0463(7) Uani 1 1 d . . . H19A H 0.4401 1.0035 0.3389 0.070 Uiso 1 1 calc R . . H19B H 0.6192 1.0204 0.4118 0.070 Uiso 1 1 calc R . . H19C H 0.4240 0.9666 0.4190 0.070 Uiso 1 1 calc R . . C20 C 0.8770(4) 0.96889(12) 0.29898(14) 0.0361(6) Uani 1 1 d . . . H20A H 0.9961 0.9387 0.2834 0.054 Uiso 1 1 calc R . . H20B H 0.9589 1.0047 0.3237 0.054 Uiso 1 1 calc R . . H20C H 0.7797 0.9828 0.2530 0.054 Uiso 1 1 calc R . . C21 C 0.8570(5) 0.90826(13) 0.42608(15) 0.0450(7) Uani 1 1 d . . . H21A H 0.7470 0.8866 0.4590 0.068 Uiso 1 1 calc R . . H21B H 0.9434 0.9406 0.4565 0.068 Uiso 1 1 calc R . . H21C H 0.9720 0.8785 0.4069 0.068 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 N1 0.0257(9) 0.0282(10) 0.0288(9) 0.0005(8) 0.0018(7) -0.0029(8) N2 0.0229(9) 0.0233(9) 0.0385(11) 0.0072(9) 0.0025(8) 0.0013(8) N3 0.0327(11) 0.0363(12) 0.0513(13) -0.0028(10) -0.0094(10) -0.0025(9) N4 0.0261(9) 0.0258(10) 0.0281(9) -0.0043(8) 0.0020(7) -0.0028(7) O1 0.0293(8) 0.0317(9) 0.0421(9) -0.0080(7) 0.0001(7) -0.0011(7) O2 0.0319(8) 0.0242(8) 0.0311(8) -0.0095(7) 0.0009(6) -0.0060(6) C1 0.0230(10) 0.0223(11) 0.0246(10) -0.0018(9) 0.0026(8) -0.0010(8) C2 0.0329(11) 0.0264(11) 0.0240(11) 0.0019(9) -0.0019(9) -0.0047(9) C3 0.0268(10) 0.0286(11) 0.0194(10) 0.0013(9) -0.0035(8) -0.0022(9) C4 0.0323(11) 0.0272(12) 0.0261(11) -0.0001(9) 0.0032(9) 0.0035(9) C5 0.0294(11) 0.0331(12) 0.0261(11) 0.0025(9) 0.0030(9) -0.0030(9) C6 0.0349(11) 0.0267(12) 0.0216(10) 0.0000(9) -0.0047(9) -0.0029(9) C7 0.0505(15) 0.0263(12) 0.0371(13) 0.0022(10) -0.0023(11) -0.0055(11) C8 0.0328(12) 0.0306(12) 0.0316(12) -0.0001(10) 0.0007(9) 0.0067(9) C9 0.0257(11) 0.0356(13) 0.0301(11) 0.0051(10) 0.0030(9) 0.0010(9) C10 0.0256(10) 0.0215(11) 0.0263(11) -0.0008(9) 0.0040(8) -0.0019(8) C11 0.0259(10) 0.0185(10) 0.0268(11) 0.0038(8) 0.0039(8) -0.0047(8) C12 0.0280(11) 0.0251(11) 0.0296(11) -0.0001(9) 0.0056(9) 0.0018(9) C13 0.0401(13) 0.0286(12) 0.0260(11) -0.0022(9) 0.0064(9) 0.0022(10) C14 0.0388(12) 0.0297(12) 0.0259(11) 0.0032(10) -0.0009(9) -0.0018(10) C15 0.0292(11) 0.0243(11) 0.0364(12) 0.0030(10) -0.0002(9) 0.0008(9) C16 0.0306(11) 0.0205(11) 0.0316(11) -0.0002(9) 0.0053(9) -0.0006(9) C17 0.0328(12) 0.0226(11) 0.0235(10) 0.0016(9) 0.0025(9) -0.0024(9) C18 0.0310(11) 0.0236(11) 0.0267(11) -0.0056(9) -0.0026(9) -0.0073(9) C19 0.0446(14) 0.0396(15) 0.0548(16) -0.0211(13) 0.0034(12) -0.0036(12) C20 0.0407(13) 0.0321(13) 0.0350(12) -0.0001(10) -0.0014(10) -0.0108(10) C21 0.0574(16) 0.0404(15) 0.0354(13) 0.0068(12) -0.0134(12) -0.0125(12) _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 N1 N2 1.232(3) . ? N1 C1 1.497(3) . ? N2 N3 1.136(3) . ? N4 C17 1.359(3) . ? N4 C10 1.450(3) . ? N4 H4 0.8600 . ? O1 C17 1.213(3) . ? O2 C17 1.340(3) . ? O2 C18 1.487(2) . ? C1 C2 1.529(3) . ? C1 C10 1.546(3) . ? C1 H1 0.9800 . ? C2 C3 1.514(3) . ? C3 C9 1.387(3) . ? C3 C4 1.389(3) . ? C4 C5 1.385(3) . ? C4 H4A 0.9300 . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 C8 1.386(3) . ? C6 C7 1.504(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.391(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.517(3) . ? C10 H10 0.9800 . ? C11 C16 1.393(3) . ? C11 C12 1.401(3) . ? C12 C13 1.378(3) . ? C12 H12 0.9300 . ? C13 C14 1.383(3) . ? C13 H13 0.9300 . ? C14 C15 1.381(3) . ? C14 H14 0.9300 . ? C15 C16 1.389(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C18 C21 1.505(3) . ? C18 C20 1.511(3) . ? C18 C19 1.514(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 N2 N1 C1 114.33(16) . . ? N3 N2 N1 172.9(2) . . ? C17 N4 C10 121.44(17) . . ? C17 N4 H4 119.3 . . ? C10 N4 H4 119.3 . . ? C17 O2 C18 121.17(16) . . ? N1 C1 C2 107.77(16) . . ? N1 C1 C10 109.12(16) . . ? C2 C1 C10 114.35(17) . . ? N1 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? C10 C1 H1 108.5 . . ? C3 C2 C1 111.11(17) . . ? C9 C3 C4 117.5(2) . . ? C9 C3 C2 121.69(18) . . ? C4 C3 C2 120.75(19) . . ? C5 C4 C3 121.0(2) . . ? C5 C4 H4A 119.5 . . ? C3 C4 H4A 119.5 . . ? C6 C5 C4 121.7(2) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C8 117.5(2) . . ? C5 C6 C7 120.7(2) . . ? C8 C6 C7 121.7(2) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 C9 121.1(2) . . ? C6 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C3 C9 C8 121.1(2) . . ? C3 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? N4 C10 C11 113.68(17) . . ? N4 C10 C1 112.56(16) . . ? C11 C10 C1 109.20(16) . . ? N4 C10 H10 107.0 . . ? C11 C10 H10 107.0 . . ? C1 C10 H10 107.0 . . ? C16 C11 C12 118.10(19) . . ? C16 C11 C10 123.12(18) . . ? C12 C11 C10 118.55(18) . . ? C13 C12 C11 121.1(2) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 120.2(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.5(2) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.6(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 120.4(2) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? O1 C17 O2 125.72(19) . . ? O1 C17 N4 124.4(2) . . ? O2 C17 N4 109.84(18) . . ? O2 C18 C21 109.63(18) . . ? O2 C18 C20 111.23(16) . . ? C21 C18 C20 112.47(19) . . ? O2 C18 C19 101.99(16) . . ? C21 C18 C19 111.6(2) . . ? C20 C18 C19 109.5(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C1 N1 N2 N3 172.9(17) . . . . ? N2 N1 C1 C2 -139.47(18) . . . . ? N2 N1 C1 C10 95.8(2) . . . . ? N1 C1 C2 C3 64.4(2) . . . . ? C10 C1 C2 C3 -174.05(16) . . . . ? C1 C2 C3 C9 89.5(2) . . . . ? C1 C2 C3 C4 -88.2(2) . . . . ? C9 C3 C4 C5 -0.6(3) . . . . ? C2 C3 C4 C5 177.14(19) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C4 C5 C6 C8 1.4(3) . . . . ? C4 C5 C6 C7 -176.6(2) . . . . ? C5 C6 C8 C9 -1.3(3) . . . . ? C7 C6 C8 C9 176.7(2) . . . . ? C4 C3 C9 C8 0.8(3) . . . . ? C2 C3 C9 C8 -176.98(19) . . . . ? C6 C8 C9 C3 0.2(3) . . . . ? C17 N4 C10 C11 -123.0(2) . . . . ? C17 N4 C10 C1 112.2(2) . . . . ? N1 C1 C10 N4 67.7(2) . . . . ? C2 C1 C10 N4 -53.0(2) . . . . ? N1 C1 C10 C11 -59.5(2) . . . . ? C2 C1 C10 C11 179.71(17) . . . . ? N4 C10 C11 C16 -26.0(3) . . . . ? C1 C10 C11 C16 100.6(2) . . . . ? N4 C10 C11 C12 159.62(17) . . . . ? C1 C10 C11 C12 -73.8(2) . . . . ? C16 C11 C12 C13 -0.8(3) . . . . ? C10 C11 C12 C13 173.83(19) . . . . ? C11 C12 C13 C14 0.6(3) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C14 C15 C16 C11 0.2(3) . . . . ? C12 C11 C16 C15 0.4(3) . . . . ? C10 C11 C16 C15 -173.98(19) . . . . ? C18 O2 C17 O1 1.0(3) . . . . ? C18 O2 C17 N4 -179.30(17) . . . . ? C10 N4 C17 O1 -4.8(3) . . . . ? C10 N4 C17 O2 175.48(17) . . . . ? C17 O2 C18 C21 -67.9(2) . . . . ? C17 O2 C18 C20 57.2(2) . . . . ? C17 O2 C18 C19 173.82(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.752 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 913690'