# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. #============================================================================== # SUBMISSION DETAILS _journal_coden_Cambridge 0177 _publ_contact_author_name 'David Parker' _publ_contact_author_address ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; _publ_contact_author_email David.Parker@durham.ac.uk _publ_contact_author_phone '0191 334 2033' _publ_contact_author_fax '0191 384 4737' _publ_section_title_footnote ; ? ; loop_ _publ_author_name _publ_author_address P.Atkinson ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; K.S.Findlay ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; F.Kielar ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; R.Pal ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; D.Parker ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; R.A.Poole ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; ; H.Puschmann ; ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; S.Richardson ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; 'Stenson. Philip A.' ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; A.L.Thompson ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; J.Yu ;Department of Chemistry, University of Durham, South Rd., Durham. DH1 3LE ; _publ_section_title ; Azaxanthones and Azathioxanthones as Sensitisers for Europium and Terbium Luminescence ; _publ_section_abstract ; Several azaxanthone? and azathioxanthone sensitising chromophores have been incorporated into macrocyclic ligands and form well-defined Eu and Tb complexes in polar media. Excitation of the heterocyclic chromophore in the rnage 330 to 375 nm leads to modest amounts of aromatic fluorescence and relatively efficient metal-based luminescence, with absolute metal-based quantum yields of up to 24% in aqueous media. ; #============================================================================== data_5b _database_code_depnum_ccdc_archive 'CCDC 296391' #============================================================================== _chemical_name_systematic ; 9-methoxy-2-methyl-1-azaxanthone ; _chemical_name_common 9-methoxy-2-methyl-1-azaxanthone _chemical_melting_point 'not measured' _chemical_formula_moiety 'C14 H11 N O3' _chemical_formula_sum 'C14 H11 N O3' _chemical_formula_weight 241.24 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z _cell_length_a 3.8200(6) _cell_length_b 9.5681(16) _cell_length_c 14.756(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.579(4) _cell_angle_gamma 90.00 _cell_volume 538.30(15) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2114 _cell_measurement_theta_min 2.539 _cell_measurement_theta_max 28.000 _exptl_crystal_description needle _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type Integration _exptl_absorpt_correction_T_min 0.9814 _exptl_absorpt_correction_T_max 0.9961 _exptl_absorpt_process_details 'XPREP (SHELXTL,1997)' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 0.00 0.00 0.6000 -1.00 0.00 0.00 0.6000 0.00 1.00 0.00 0.0200 0.00 -1.00 0.00 0.0200 0.00 0.00 1.00 0.0200 0.00 0.00 -1.00 0.0200 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 3 sets of \w scans each set at different \f and/or 2\q angles and each scan (40s exposure) covering 0.3\% in \w. Crystal to detector distance 5.965 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus X-ray source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker ProteumM with Bede Microsource' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 1380 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.538 _diffrn_reflns_theta_max 28.272 _reflns_number_total 1380 _reflns_number_gt 904 _reflns_threshold_expression I>3.00u(I) _computing_data_collection 'SMART-NT V6.1 (Bruker, 2000)' _computing_cell_refinement 'SMART-NT V6.1 (Bruker, 2000)' _computing_data_reduction 'SAINT-NT V6.45A (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _refine_special_details ; Because the data were collected with molybdenum radiation, there were no measurable anomalous differences, as a consequence of which it was admissible to merge Friedel pairs of reflections. Hydrogen atoms were placed geometrically after each cycle. The crystal was found to be a non-merohedral twin byt rotation around the 1 0 0, so the structure was refined with the twin law: 1 0 0 0 -1 0 -0.482 0 -1. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.311 0.196 0.171 ; _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 . _chemical_absolute_configuration unk _refine_ls_number_reflns 904 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0276 _refine_ls_R_factor_ref 0.0276 _refine_ls_wR_factor_all 0.0411 _refine_ls_wR_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0297 _refine_ls_goodness_of_fit_ref 1.0770 _refine_ls_shift/su_max 0.000103 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _oxford_refine_ls_scale 0.5306(13) loop_ _oxford_twin_element_scale_factors 0.6805(18) 0.3195(18) 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N -0.2503(7) 0.6950(2) 0.07088(16) 0.0186 1.0000 Uani . . . . . . O1 O 0.3435(6) 0.4828(2) 0.32984(13) 0.0252 1.0000 Uani . . . . . . O2 O -0.1259(5) 0.8181(2) 0.19790(12) 0.0181 1.0000 Uani . . . . . . O3 O -0.1787(7) 1.0625(2) 0.27016(12) 0.0230 1.0000 Uani . . . . . . C1 C -0.3951(9) 0.5814(3) -0.07301(19) 0.0235 1.0000 Uani . . . . . . C2 C -0.2398(8) 0.5779(3) 0.02261(18) 0.0199 1.0000 Uani . . . . . . C3 C -0.0895(8) 0.4539(3) 0.05794(19) 0.0206 1.0000 Uani . . . . . . C4 C 0.0553(8) 0.4536(3) 0.1455(2) 0.0207 1.0000 Uani . . . . . . C5 C 0.0480(8) 0.5754(3) 0.19776(17) 0.0165 1.0000 Uani . . . . . . C6 C -0.1051(8) 0.6921(3) 0.15514(18) 0.0167 1.0000 Uani . . . . . . C7 C 0.2024(8) 0.5823(3) 0.29151(19) 0.0182 1.0000 Uani . . . . . . C8 C 0.1669(8) 0.7210(3) 0.33426(19) 0.0166 1.0000 Uani . . . . . . C9 C 0.0094(8) 0.8300(3) 0.28588(19) 0.0170 1.0000 Uani . . . . . . C10 C 0.2945(7) 0.7435(3) 0.42492(18) 0.0203 1.0000 Uani . . . . . . C11 C 0.2590(8) 0.8731(3) 0.46334(19) 0.0223 1.0000 Uani . . . . . . C12 C 0.0982(8) 0.9827(3) 0.41420(18) 0.0194 1.0000 Uani . . . . . . C13 C -0.0222(8) 0.9637(3) 0.32575(19) 0.0181 1.0000 Uani . . . . . . C14 C -0.2419(8) 1.1951(3) 0.31103(19) 0.0227 1.0000 Uani . . . . . . H1A H -0.5289 0.6665 -0.0819 0.0342 1.0000 Uiso R . . . . . H1B H -0.2056 0.5786 -0.1155 0.0353 1.0000 Uiso R . . . . . H1C H -0.5379 0.4977 -0.0874 0.0351 1.0000 Uiso R . . . . . H3 H -0.0923 0.3720 0.0238 0.0242 1.0000 Uiso R . . . . . H4 H 0.1699 0.3695 0.1745 0.0246 1.0000 Uiso R . . . . . H10 H 0.4028 0.6644 0.4554 0.0241 1.0000 Uiso R . . . . . H11 H 0.3385 0.8873 0.5205 0.0249 1.0000 Uiso R . . . . . H12 H 0.0758 1.0685 0.4441 0.0221 1.0000 Uiso R . . . . . H14A H -0.3693 1.2463 0.2646 0.0328 1.0000 Uiso R . . . . . H14B H -0.0181 1.2428 0.3288 0.0336 1.0000 Uiso R . . . . . H14C H -0.3867 1.1853 0.3666 0.0335 1.0000 Uiso 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 0.0203(12) 0.0190(11) 0.0168(11) 0.0020(10) 0.0019(10) -0.0012(11) O1 0.0321(12) 0.0191(10) 0.0235(10) 0.0047(9) -0.0054(9) 0.0054(10) O2 0.0250(12) 0.0133(9) 0.0157(10) 0.0007(8) -0.0027(8) 0.0059(9) O3 0.0338(12) 0.0162(10) 0.0183(10) -0.0027(9) -0.0037(9) 0.0059(9) C1 0.0290(17) 0.0225(15) 0.0182(13) -0.0023(12) -0.0040(12) 0.0005(14) C2 0.0203(15) 0.0238(14) 0.0155(12) 0.0004(12) 0.0007(12) -0.0046(14) C3 0.0250(16) 0.0150(14) 0.0219(14) -0.0035(12) 0.0016(12) 0.0012(13) C4 0.0209(15) 0.0164(14) 0.0250(14) 0.0008(12) 0.0037(12) -0.0011(13) C5 0.0180(14) 0.0159(12) 0.0160(12) 0.0024(11) 0.0033(11) 0.0023(13) C6 0.0189(15) 0.0136(13) 0.0177(14) -0.0012(11) 0.0028(11) -0.0025(13) C7 0.0161(16) 0.0185(14) 0.0202(13) 0.0003(12) 0.0020(11) 0.0006(13) C8 0.0141(14) 0.0179(15) 0.0180(13) 0.0002(10) 0.0027(11) -0.0014(12) C9 0.0174(15) 0.0193(15) 0.0142(12) -0.0001(11) 0.0008(11) -0.0032(12) C10 0.0179(16) 0.0260(16) 0.0168(14) 0.0075(12) -0.0009(12) -0.0004(13) C11 0.0218(15) 0.0309(16) 0.0136(12) 0.0007(12) -0.0039(12) -0.0035(13) C12 0.0209(14) 0.0194(14) 0.0175(13) -0.0028(13) -0.0009(12) -0.0032(14) C13 0.0181(14) 0.0159(14) 0.0207(13) 0.0053(12) 0.0032(11) 0.0015(12) C14 0.0245(16) 0.0174(13) 0.0257(15) -0.0025(12) -0.0030(12) 0.0007(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C2 . 1.330(4) yes N1 . C6 . 1.330(4) yes O1 . C7 . 1.216(4) yes O2 . C6 . 1.365(4) yes O2 . C9 . 1.372(3) yes O3 . C13 . 1.365(4) yes O3 . C14 . 1.431(3) yes C1 . C2 . 1.497(4) yes C1 . H1A . 0.966 no C1 . H1B . 0.988 no C1 . H1C . 0.985 no C2 . C3 . 1.404(4) yes C3 . C4 . 1.374(4) yes C3 . H3 . 0.931 no C4 . C5 . 1.399(4) yes C4 . H4 . 0.999 no C5 . C6 . 1.392(4) yes C5 . C7 . 1.471(4) yes C7 . C8 . 1.479(4) yes C8 . C9 . 1.380(4) yes C8 . C10 . 1.411(4) yes C9 . C13 . 1.417(4) yes C10 . C11 . 1.373(4) yes C10 . H10 . 0.961 no C11 . C12 . 1.396(4) yes C11 . H11 . 0.889 no C12 . C13 . 1.369(4) yes C12 . H12 . 0.938 no C14 . H14A . 0.951 no C14 . H14B . 0.990 no C14 . H14C . 1.022 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C6 . 117.3(3) yes C6 . O2 . C9 . 118.8(2) yes C13 . O3 . C14 . 116.1(2) yes C2 . C1 . H1A . 108.8 no C2 . C1 . H1B . 109.6 no H1A . C1 . H1B . 109.8 no C2 . C1 . H1C . 111.5 no H1A . C1 . H1C . 112.0 no H1B . C1 . H1C . 105.0 no C1 . C2 . N1 . 117.5(3) yes C1 . C2 . C3 . 119.9(3) yes N1 . C2 . C3 . 122.6(2) yes C2 . C3 . C4 . 118.8(3) yes C2 . C3 . H3 . 121.3 no C4 . C3 . H3 . 119.9 no C3 . C4 . C5 . 119.8(3) yes C3 . C4 . H4 . 122.9 no C5 . C4 . H4 . 117.3 no C4 . C5 . C6 . 116.2(2) yes C4 . C5 . C7 . 122.3(3) yes C6 . C5 . C7 . 121.4(3) yes C5 . C6 . O2 . 122.3(2) yes C5 . C6 . N1 . 125.3(3) yes O2 . C6 . N1 . 112.4(3) yes C5 . C7 . O1 . 122.8(3) yes C5 . C7 . C8 . 113.5(3) yes O1 . C7 . C8 . 123.6(3) yes C7 . C8 . C9 . 120.4(2) yes C7 . C8 . C10 . 120.4(3) yes C9 . C8 . C10 . 119.3(2) yes C8 . C9 . O2 . 123.6(2) yes C8 . C9 . C13 . 120.9(2) yes O2 . C9 . C13 . 115.5(2) yes C8 . C10 . C11 . 119.5(3) yes C8 . C10 . H10 . 115.9 no C11 . C10 . H10 . 124.6 no C10 . C11 . C12 . 121.0(3) yes C10 . C11 . H11 . 119.6 no C12 . C11 . H11 . 119.4 no C11 . C12 . C13 . 120.4(3) yes C11 . C12 . H12 . 117.6 no C13 . C12 . H12 . 122.0 no C9 . C13 . C12 . 118.9(3) yes C9 . C13 . O3 . 114.9(2) yes C12 . C13 . O3 . 126.1(3) yes O3 . C14 . H14A . 104.2 no O3 . C14 . H14B . 110.8 no H14A . C14 . H14B . 110.4 no O3 . C14 . H14C . 111.8 no H14A . C14 . H14C . 110.3 no H14B . C14 . H14C . 109.3 no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_site_symmetry_1 _geom_torsion_atom_site_label_2 _geom_torsion_site_symmetry_2 _geom_torsion_atom_site_label_3 _geom_torsion_site_symmetry_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 . N1 . C2 . C3 . 1.0(4) no C6 . N1 . C2 . C1 . -178.4(3) no N1 . C2 . C3 . C4 . -0.6(5) no C1 . C2 . C3 . C4 . 179.2(3) no C2 . C3 . C4 . C5 . 0.8(4) no C3 . C4 . C5 . C6 . -1.4(4) no C3 . C4 . C5 . C7 . -179.5(3) no C2 . N1 . C6 . O2 . 179.3(3) no C2 . N1 . C6 . C5 . -1.8(5) no C9 . O2 . C6 . N1 . 179.2(2) no C9 . O2 . C6 . C5 . 0.3(4) no C7 . C5 . C6 . N1 . -180.0(3) no C4 . C5 . C6 . O2 . -179.2(3) no C7 . C5 . C6 . O2 . -1.1(5) no C6 . C5 . C7 . O1 . -178.5(4) no C4 . C5 . C7 . O1 . -0.5(5) no C6 . C5 . C7 . C8 . 1.7(4) no C4 . C5 . C7 . C8 . 179.7(3) no O1 . C7 . C8 . C9 . 178.7(3) no C5 . C7 . C8 . C9 . -1.6(4) no O1 . C7 . C8 . C10 . -1.2(5) no C5 . C7 . C8 . C10 . 178.5(3) no C10 . C8 . C9 . C13 . 0.6(4) no C7 . C8 . C9 . C13 . -179.3(3) no C10 . C8 . C9 . O2 . -179.3(3) no C7 . C8 . C9 . O2 . 0.9(5) no C6 . O2 . C9 . C13 . -180.0(3) no C6 . O2 . C9 . C8 . -0.1(4) no C9 . C8 . C10 . C11 . 0.3(5) no C7 . C8 . C10 . C11 . -179.9(3) no C11 . C12 . C13 . O3 . -178.9(3) no C8 . C10 . C11 . C12 . -0.2(5) no C14 . O3 . C13 . C9 . 174.5(3) no C14 . O3 . C13 . C12 . -4.4(5) no C10 . C11 . C12 . C13 . -0.8(5) no O3 . C13 . C9 . C8 . 178.9(3) no C8 . C9 . C13 . C12 . -1.5(5) no O2 . C9 . C13 . C12 . 178.3(3) no C11 . C12 . C13 . C9 . 1.6(5) no _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.424 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.20 _refine_diff_density_min -0.16 #============================================================================== data_5a _database_code_depnum_ccdc_archive 'CCDC 296392' #============================================================================== _chemical_name_systematic ; 7-methoxy-2-methyl-1-azaxanthone ; _chemical_name_common 7-methoxy-2-methyl-1-azaxanthone _chemical_melting_point 'not measured' _chemical_formula_moiety 'C14 H11 N O3' _chemical_formula_sum 'C14 H11 N O3' _chemical_formula_weight 241.24 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 P2(1)/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 12.191(2) _cell_length_b 3.8876(8) _cell_length_c 22.922(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.223(6) _cell_angle_gamma 90.00 _cell_volume 1086.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 756 _cell_measurement_theta_min 3.141 _cell_measurement_theta_max 22.400 _exptl_crystal_description needle _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type Integration _exptl_absorpt_correction_T_min 0.9774 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details 'XPREP (SHELXTL,1997)' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 1.00 0.0100 0.00 0.00 -1.00 0.0100 1.00 0.00 0.00 0.0200 -1.00 0.00 0.00 0.0200 0.00 1.00 0.00 0.2000 0.00 -1.00 0.00 0.2000 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 3 sets of \w scans each set at different \f and/or 2\q angles and each scan (60s exposure) covering 0.3\% in \w. Crystal to detector distance 4.965 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus X-ray source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker ProteumM with Bede Microsource' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 9590 _diffrn_reflns_av_R_equivalents 0.1274 _diffrn_reflns_av_sigmaI/netI 0.1374 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 0.89 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2132 _reflns_number_gt 1084 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V6.1 (Bruker, 2000)' _computing_cell_refinement 'SMART-NT V6.1 (Bruker, 2000)' _computing_data_reduction 'SAINT-NT V6.45A (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. The crystal was found to be a merohedral twin, with monoclinic emulating orthorhombic, so the structure was refined using a twin law: 1 0 0 0 -1 0 0 0 -1. ; _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^)+(0.0795P)^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 2132 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1239 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1608 _refine_ls_wR_factor_gt 0.1416 _refine_ls_goodness_of_fit_ref 0.850 _refine_ls_restrained_S_all 0.850 _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 O1 O 0.4765(3) -0.2683(9) 0.22093(13) 0.0286(8) Uani 1 1 d . . . O2 O 0.4557(3) 0.2504(9) 0.06470(13) 0.0244(8) Uani 1 1 d . . . O3 O 0.8681(3) -0.1622(9) 0.13517(13) 0.0274(9) Uani 1 1 d . . . N1 N 0.2720(3) 0.2985(10) 0.06973(15) 0.0210(9) Uani 1 1 d . . . C1 C 0.0758(4) 0.3674(14) 0.0655(2) 0.0297(13) Uani 1 1 d . . . H1A H 0.0828 0.3181 0.0246 0.045 Uiso 1 1 calc R . . H1B H 0.0671 0.6107 0.0709 0.045 Uiso 1 1 calc R . . H1C H 0.0129 0.2497 0.0807 0.045 Uiso 1 1 calc R . . C2 C 0.1780(4) 0.2468(12) 0.09740(19) 0.0214(11) Uani 1 1 d . . . C3 C 0.1711(4) 0.0916(12) 0.1521(2) 0.0276(13) Uani 1 1 d . . . H3 H 0.1039 0.0676 0.1708 0.033 Uiso 1 1 calc R . . C4 C 0.2666(4) -0.0253(12) 0.1779(2) 0.0259(12) Uani 1 1 d . . . H4 H 0.2640 -0.1326 0.2141 0.031 Uiso 1 1 calc R . . C5 C 0.3673(4) 0.0172(13) 0.14959(18) 0.0190(11) Uani 1 1 d . . . C6 C 0.3639(4) 0.1832(12) 0.09671(18) 0.0196(10) Uani 1 1 d . . . C7 C 0.4714(4) -0.1084(12) 0.17497(19) 0.0193(11) Uani 1 1 d . . . C8 C 0.5669(4) -0.0330(12) 0.13968(19) 0.0196(11) Uani 1 1 d . . . C9 C 0.5569(4) 0.1371(12) 0.08624(19) 0.0192(11) Uani 1 1 d . . . C10 C 0.6733(4) -0.1379(12) 0.1572(2) 0.0230(11) Uani 1 1 d . . . H10 H 0.6834 -0.2529 0.1924 0.028 Uiso 1 1 calc R . . C11 C 0.7610(4) -0.0693(12) 0.12214(19) 0.0233(11) Uani 1 1 d . . . C12 C 0.7478(4) 0.1058(12) 0.06953(18) 0.0224(11) Uani 1 1 d . . . H12 H 0.8088 0.1525 0.0466 0.027 Uiso 1 1 calc R . . C13 C 0.6451(4) 0.2105(12) 0.05112(18) 0.0232(11) Uani 1 1 d . . . H13 H 0.6358 0.3272 0.0160 0.028 Uiso 1 1 calc R . . C14 C 0.8863(4) -0.3331(12) 0.18932(19) 0.0268(12) Uani 1 1 d . . . H14A H 0.9628 -0.3863 0.1934 0.040 Uiso 1 1 calc R . . H14B H 0.8443 -0.5420 0.1903 0.040 Uiso 1 1 calc R . . H14C H 0.8640 -0.1862 0.2208 0.040 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 0.0224(19) 0.038(2) 0.0255(17) 0.0073(16) -0.0075(14) -0.0050(17) O2 0.0152(18) 0.0303(19) 0.0276(16) 0.0050(16) -0.0119(15) -0.0002(16) O3 0.0149(19) 0.036(2) 0.0309(18) 0.0052(15) -0.0090(15) 0.0042(16) N1 0.015(2) 0.022(2) 0.0250(19) -0.0003(18) -0.0099(18) 0.0030(18) C1 0.019(3) 0.033(3) 0.038(3) 0.001(2) -0.011(2) 0.005(2) C2 0.019(3) 0.020(3) 0.025(2) -0.003(2) -0.008(2) -0.003(2) C3 0.016(3) 0.029(3) 0.037(3) -0.003(2) -0.003(2) -0.001(2) C4 0.030(3) 0.022(3) 0.026(2) -0.002(2) -0.013(2) 0.001(2) C5 0.017(3) 0.021(3) 0.019(2) -0.0047(19) -0.002(2) -0.002(2) C6 0.015(2) 0.021(3) 0.023(2) -0.002(2) -0.006(2) 0.000(2) C7 0.019(3) 0.018(2) 0.021(2) -0.003(2) -0.005(2) -0.004(2) C8 0.018(3) 0.016(3) 0.024(3) -0.003(2) -0.008(2) -0.002(2) C9 0.014(3) 0.023(3) 0.021(2) -0.005(2) -0.0055(19) 0.002(2) C10 0.021(3) 0.021(3) 0.026(2) 0.000(2) -0.009(2) 0.004(2) C11 0.017(3) 0.020(3) 0.033(3) -0.004(2) -0.006(2) 0.006(2) C12 0.019(3) 0.027(3) 0.021(2) 0.002(2) 0.000(2) 0.002(2) C13 0.019(3) 0.027(3) 0.023(2) 0.004(2) -0.009(2) -0.002(2) C14 0.024(3) 0.027(3) 0.030(3) 0.003(2) -0.011(2) 0.002(2) _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 C7 1.225(5) . ? O2 C6 1.365(6) . ? O2 C9 1.398(5) . ? O3 C11 1.386(5) . ? O3 C14 1.425(5) . ? N1 C2 1.328(6) . ? N1 C6 1.354(5) . ? C1 C2 1.516(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.395(6) . ? C3 C4 1.380(7) . ? C3 H3 0.9300 . ? C4 C5 1.401(7) . ? C4 H4 0.9300 . ? C5 C6 1.374(6) . ? C5 C7 1.477(7) . ? C7 C8 1.451(6) . ? C8 C9 1.397(6) . ? C8 C10 1.416(6) . ? C9 C13 1.376(6) . ? C10 C11 1.366(7) . ? C10 H10 0.9300 . ? C11 C12 1.394(6) . ? C12 C13 1.381(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 C6 O2 C9 118.3(3) . . ? C11 O3 C14 116.9(4) . . ? C2 N1 C6 116.5(4) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 123.4(4) . . ? N1 C2 C1 115.6(4) . . ? C3 C2 C1 121.0(4) . . ? C4 C3 C2 118.3(5) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C3 C4 C5 120.1(4) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 116.2(4) . . ? C6 C5 C7 121.7(4) . . ? C4 C5 C7 122.1(4) . . ? N1 C6 O2 111.7(4) . . ? N1 C6 C5 125.5(4) . . ? O2 C6 C5 122.9(4) . . ? O1 C7 C8 122.9(4) . . ? O1 C7 C5 123.2(4) . . ? C8 C7 C5 113.8(4) . . ? C9 C8 C10 117.5(4) . . ? C9 C8 C7 121.1(4) . . ? C10 C8 C7 121.3(4) . . ? C13 C9 C8 123.0(4) . . ? C13 C9 O2 114.8(4) . . ? C8 C9 O2 122.2(4) . . ? C11 C10 C8 119.7(4) . . ? C11 C10 H10 120.2 . . ? C8 C10 H10 120.2 . . ? C10 C11 O3 124.2(4) . . ? C10 C11 C12 121.1(4) . . ? O3 C11 C12 114.8(4) . . ? C13 C12 C11 120.6(4) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C9 C13 C12 118.0(4) . . ? C9 C13 H13 121.0 . . ? C12 C13 H13 121.0 . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C6 N1 C2 C3 1.8(7) . . . . ? C6 N1 C2 C1 -178.1(4) . . . . ? N1 C2 C3 C4 -2.4(7) . . . . ? C1 C2 C3 C4 177.4(4) . . . . ? C2 C3 C4 C5 0.9(7) . . . . ? C3 C4 C5 C6 1.0(7) . . . . ? C3 C4 C5 C7 -179.0(5) . . . . ? C2 N1 C6 O2 -179.8(4) . . . . ? C2 N1 C6 C5 0.4(7) . . . . ? C9 O2 C6 N1 -178.2(4) . . . . ? C9 O2 C6 C5 1.6(6) . . . . ? C4 C5 C6 N1 -1.8(7) . . . . ? C7 C5 C6 N1 178.3(4) . . . . ? C4 C5 C6 O2 178.5(4) . . . . ? C7 C5 C6 O2 -1.5(7) . . . . ? C6 C5 C7 O1 -177.2(5) . . . . ? C4 C5 C7 O1 2.8(7) . . . . ? C6 C5 C7 C8 1.2(6) . . . . ? C4 C5 C7 C8 -178.7(4) . . . . ? O1 C7 C8 C9 177.2(4) . . . . ? C5 C7 C8 C9 -1.3(6) . . . . ? O1 C7 C8 C10 -0.9(7) . . . . ? C5 C7 C8 C10 -179.4(4) . . . . ? C10 C8 C9 C13 -1.2(7) . . . . ? C7 C8 C9 C13 -179.3(4) . . . . ? C10 C8 C9 O2 179.7(4) . . . . ? C7 C8 C9 O2 1.6(7) . . . . ? C6 O2 C9 C13 179.2(4) . . . . ? C6 O2 C9 C8 -1.7(6) . . . . ? C9 C8 C10 C11 0.3(6) . . . . ? C7 C8 C10 C11 178.5(5) . . . . ? C8 C10 C11 O3 -179.7(4) . . . . ? C8 C10 C11 C12 0.6(7) . . . . ? C14 O3 C11 C10 -1.4(6) . . . . ? C14 O3 C11 C12 178.2(4) . . . . ? C10 C11 C12 C13 -0.9(7) . . . . ? O3 C11 C12 C13 179.5(4) . . . . ? C8 C9 C13 C12 1.0(7) . . . . ? O2 C9 C13 C12 -179.9(4) . . . . ? C11 C12 C13 C9 0.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.267 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.068 #============================================================================== data_6 _database_code_depnum_ccdc_archive 'CCDC 296393' #============================================================================== _chemical_name_systematic ; 6-Ethylamino-2-methyl-1-azaxanthone ; _chemical_name_common 6-Ethylamino-2-methyl-1-azaxanthone _chemical_melting_point 'not measured' _chemical_formula_moiety 'C15 H14 N2 O2' _chemical_formula_sum 'C15 H14 N2 O2' _chemical_formula_weight 254.28 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 P2(1)/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 4.5840(3) _cell_length_b 11.1889(7) _cell_length_c 24.2034(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.953(3) _cell_angle_gamma 90.00 _cell_volume 1241.22(14) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1124 _cell_measurement_theta_min 2.480 _cell_measurement_theta_max 26.054 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.708511 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of \w scans at different \f and/or 2\q angles, each scan covering 0.3\% in \w. Crystal to detector distance 4.51 \ 5.81 \ 4.965cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 7428 _diffrn_reflns_av_R_equivalents 0.1251 _diffrn_reflns_av_sigmaI/netI 0.1399 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.07 _reflns_number_total 2722 _reflns_number_gt 1112 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V6.1 (Bruker, 2000)' _computing_cell_refinement 'SMART-NT V6.1 (Bruker, 2000)' _computing_data_reduction 'SAINT-NT V6.45A (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0559P)^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 SHELXL _refine_ls_extinction_coef 0.013(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2722 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1531 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1502 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 0.867 _refine_ls_restrained_S_all 0.867 _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 O1 O 0.2076(5) 0.15916(19) 0.32019(8) 0.0381(6) Uani 1 1 d . . . O2 O 0.4535(5) 0.42802(18) 0.42751(7) 0.0341(6) Uani 1 1 d . . . N1 N 0.7531(6) 0.5108(2) 0.36615(9) 0.0343(7) Uani 1 1 d . . . N2 N -0.1483(6) 0.0756(2) 0.39775(10) 0.0363(7) Uani 1 1 d . . . H2 H -0.0829 0.0713 0.3638 0.044 Uiso 1 1 calc R . . C1 C 1.0799(8) 0.6146(3) 0.30458(12) 0.0383(8) Uani 1 1 d . . . H1A H 0.9796 0.6765 0.2829 0.058 Uiso 1 1 calc R . . H1B H 1.2460 0.5841 0.2839 0.058 Uiso 1 1 calc R . . H1C H 1.1498 0.6486 0.3397 0.058 Uiso 1 1 calc R . . C2 C 0.8732(7) 0.5147(3) 0.31577(12) 0.0326(8) Uani 1 1 d . . . C3 C 0.8011(7) 0.4295(3) 0.27473(12) 0.0357(8) Uani 1 1 d . . . H3 H 0.8865 0.4343 0.2393 0.043 Uiso 1 1 calc R . . C4 C 0.6073(7) 0.3396(3) 0.28616(11) 0.0333(8) Uani 1 1 d . . . H4 H 0.5592 0.2817 0.2588 0.040 Uiso 1 1 calc R . . C5 C 0.4819(7) 0.3340(3) 0.33802(11) 0.0281(7) Uani 1 1 d . . . C6 C 0.5656(7) 0.4229(3) 0.37578(11) 0.0301(7) Uani 1 1 d . . . C7 C 0.2758(7) 0.2406(3) 0.35338(11) 0.0329(8) Uani 1 1 d . . . C8 C 0.1555(7) 0.2499(3) 0.40896(12) 0.0288(7) Uani 1 1 d . . . C9 C 0.2535(7) 0.3435(3) 0.44409(12) 0.0333(8) Uani 1 1 d . . . C10 C -0.0511(7) 0.1674(3) 0.43021(11) 0.0309(7) Uani 1 1 d . . . C11 C -0.1547(7) 0.1828(3) 0.48397(11) 0.0352(8) Uani 1 1 d . . . H11 H -0.2957 0.1295 0.4984 0.042 Uiso 1 1 calc R . . C12 C -0.0477(7) 0.2775(3) 0.51603(11) 0.0359(8) Uani 1 1 d . . . H12 H -0.1187 0.2871 0.5524 0.043 Uiso 1 1 calc R . . C13 C 0.1559(7) 0.3574(3) 0.49723(11) 0.0352(8) Uani 1 1 d . . . H13 H 0.2269 0.4203 0.5202 0.042 Uiso 1 1 calc R . . C14 C -0.3524(8) -0.0155(3) 0.41534(12) 0.0359(8) Uani 1 1 d . . . H14A H -0.5419 0.0220 0.4239 0.043 Uiso 1 1 calc R . . H14B H -0.2766 -0.0547 0.4493 0.043 Uiso 1 1 calc R . . C15 C -0.3958(9) -0.1079(3) 0.37028(13) 0.0525(10) Uani 1 1 d . . . H15A H -0.4712 -0.0690 0.3367 0.079 Uiso 1 1 calc R . . H15B H -0.5356 -0.1684 0.3825 0.079 Uiso 1 1 calc R . . H15C H -0.2089 -0.1464 0.3625 0.079 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 0.0524(16) 0.0313(13) 0.0304(11) -0.0040(10) -0.0082(10) -0.0059(11) O2 0.0452(15) 0.0342(13) 0.0226(10) 0.0004(9) -0.0032(10) -0.0057(11) N1 0.0427(18) 0.0308(16) 0.0291(14) 0.0033(12) -0.0080(13) -0.0001(14) N2 0.0456(19) 0.0321(16) 0.0310(14) -0.0016(11) -0.0043(13) -0.0062(14) C1 0.047(2) 0.035(2) 0.0333(17) 0.0062(15) -0.0041(15) -0.0031(17) C2 0.037(2) 0.0304(19) 0.0300(16) 0.0046(14) -0.0083(14) 0.0034(15) C3 0.042(2) 0.038(2) 0.0269(15) 0.0006(14) -0.0030(15) 0.0046(17) C4 0.041(2) 0.0334(19) 0.0257(15) -0.0009(13) -0.0041(14) 0.0003(16) C5 0.0344(19) 0.0247(17) 0.0249(15) 0.0020(13) -0.0057(13) 0.0000(14) C6 0.0341(19) 0.0288(18) 0.0269(15) -0.0020(13) -0.0077(14) 0.0050(15) C7 0.040(2) 0.0301(18) 0.0281(16) -0.0016(13) -0.0129(15) 0.0053(15) C8 0.0314(19) 0.0266(17) 0.0281(14) 0.0023(13) -0.0051(13) 0.0016(14) C9 0.039(2) 0.0296(19) 0.0311(16) 0.0038(14) -0.0062(14) 0.0002(16) C10 0.0336(19) 0.0276(17) 0.0312(16) 0.0022(14) -0.0064(14) 0.0009(15) C11 0.039(2) 0.034(2) 0.0322(16) 0.0038(14) -0.0008(15) 0.0001(16) C12 0.043(2) 0.039(2) 0.0262(15) 0.0010(14) -0.0041(15) -0.0009(17) C13 0.044(2) 0.036(2) 0.0254(16) -0.0038(14) -0.0055(15) 0.0023(17) C14 0.042(2) 0.0274(18) 0.0376(17) 0.0030(14) -0.0068(15) -0.0001(16) C15 0.067(3) 0.036(2) 0.054(2) -0.0051(17) -0.0060(19) -0.0134(19) _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 C7 1.251(3) . ? O2 C6 1.362(3) . ? O2 C9 1.381(4) . ? N1 C6 1.329(4) . ? N1 C2 1.347(4) . ? N2 C10 1.363(4) . ? N2 C14 1.452(4) . ? N2 H2 0.8800 . ? C1 C2 1.493(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.412(4) . ? C3 C4 1.372(4) . ? C3 H3 0.9500 . ? C4 C5 1.391(4) . ? C4 H4 0.9500 . ? C5 C6 1.400(4) . ? C5 C7 1.461(4) . ? C7 C8 1.466(4) . ? C8 C9 1.418(4) . ? C8 C10 1.425(4) . ? C9 C13 1.378(4) . ? C10 C11 1.403(4) . ? C11 C12 1.397(4) . ? C11 H11 0.9500 . ? C12 C13 1.376(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.514(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 C6 O2 C9 120.1(2) . . ? C6 N1 C2 117.3(3) . . ? C10 N2 C14 124.4(3) . . ? C10 N2 H2 117.8 . . ? C14 N2 H2 117.8 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.3(3) . . ? N1 C2 C1 117.3(3) . . ? C3 C2 C1 121.3(3) . . ? C4 C3 C2 119.8(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.6(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 116.3(3) . . ? C4 C5 C7 122.7(3) . . ? C6 C5 C7 120.9(3) . . ? N1 C6 O2 112.7(3) . . ? N1 C6 C5 125.6(3) . . ? O2 C6 C5 121.7(3) . . ? O1 C7 C5 120.9(3) . . ? O1 C7 C8 123.2(3) . . ? C5 C7 C8 115.9(3) . . ? C9 C8 C10 117.9(3) . . ? C9 C8 C7 118.9(3) . . ? C10 C8 C7 123.2(3) . . ? C13 C9 O2 114.9(3) . . ? C13 C9 C8 122.6(3) . . ? O2 C9 C8 122.5(3) . . ? N2 C10 C11 121.0(3) . . ? N2 C10 C8 119.5(3) . . ? C11 C10 C8 119.5(3) . . ? C12 C11 C10 119.1(3) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C13 C12 C11 122.9(3) . . ? C13 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? C12 C13 C9 117.9(3) . . ? C12 C13 H13 121.1 . . ? C9 C13 H13 121.1 . . ? N2 C14 C15 110.2(3) . . ? N2 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? N2 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C6 N1 C2 C3 0.4(4) . . . . ? C6 N1 C2 C1 179.0(3) . . . . ? N1 C2 C3 C4 -0.7(5) . . . . ? C1 C2 C3 C4 -179.2(3) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C3 C4 C5 C7 -179.5(3) . . . . ? C2 N1 C6 O2 -179.0(3) . . . . ? C2 N1 C6 C5 0.0(5) . . . . ? C9 O2 C6 N1 179.6(3) . . . . ? C9 O2 C6 C5 0.5(4) . . . . ? C4 C5 C6 N1 -0.1(4) . . . . ? C7 C5 C6 N1 179.2(3) . . . . ? C4 C5 C6 O2 178.8(3) . . . . ? C7 C5 C6 O2 -1.8(4) . . . . ? C4 C5 C7 O1 1.5(5) . . . . ? C6 C5 C7 O1 -177.9(3) . . . . ? C4 C5 C7 C8 -177.9(3) . . . . ? C6 C5 C7 C8 2.7(4) . . . . ? O1 C7 C8 C9 178.1(3) . . . . ? C5 C7 C8 C9 -2.5(4) . . . . ? O1 C7 C8 C10 -0.3(5) . . . . ? C5 C7 C8 C10 179.0(3) . . . . ? C6 O2 C9 C13 179.8(3) . . . . ? C6 O2 C9 C8 -0.4(4) . . . . ? C10 C8 C9 C13 -0.3(4) . . . . ? C7 C8 C9 C13 -178.8(3) . . . . ? C10 C8 C9 O2 180.0(3) . . . . ? C7 C8 C9 O2 1.5(4) . . . . ? C14 N2 C10 C11 -2.5(5) . . . . ? C14 N2 C10 C8 178.3(3) . . . . ? C9 C8 C10 N2 -179.4(3) . . . . ? C7 C8 C10 N2 -1.0(4) . . . . ? C9 C8 C10 C11 1.4(4) . . . . ? C7 C8 C10 C11 179.9(3) . . . . ? N2 C10 C11 C12 179.5(3) . . . . ? C8 C10 C11 C12 -1.4(4) . . . . ? C10 C11 C12 C13 0.2(5) . . . . ? C11 C12 C13 C9 1.0(5) . . . . ? O2 C9 C13 C12 178.9(3) . . . . ? C8 C9 C13 C12 -0.9(5) . . . . ? C10 N2 C14 C15 -176.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.88 1.98 2.676(3) 135.6 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.07 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.209 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.057 #============================================================================== data_15a _database_code_depnum_ccdc_archive 'CCDC 296394' #============================================================================== _chemical_name_systematic ; 2-Methyl-1-azathioxanthone ; _chemical_name_common 2-Methyl-1-azathioxanthone _chemical_melting_point 'not measured' _chemical_formula_moiety 'C13 H9 N O S' _chemical_formula_sum 'C13 H9 N O S' _chemical_formula_weight 227.27 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 3.8693(5) _cell_length_b 12.3848(16) _cell_length_c 10.4698(13) _cell_angle_alpha 90.00 _cell_angle_beta 95.015(2) _cell_angle_gamma 90.00 _cell_volume 499.80(11) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3188 _cell_measurement_theta_min 2.508 _cell_measurement_theta_max 28.993 _exptl_crystal_description block _exptl_crystal_colour clear_intense_yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 236 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type Integration _exptl_absorpt_correction_T_min 0.93407 _exptl_absorpt_correction_T_max 0.95158 _exptl_absorpt_process_details 'XPREP (SHELXTL,1997)' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1.00 0.00 0.00 0.1000 -1.00 0.00 0.00 0.1000 0.00 1.00 -1.00 0.1100 0.00 -1.00 1.00 0.1100 0.00 1.00 1.00 0.1100 0.00 -1.00 -1.00 0.1100 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (15s exposure) covering 0.3\% in \w. Crystal to detector distance 4.50 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD 1K area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 8 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 5541 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 29.11 _reflns_number_total 2632 _reflns_number_gt 2259 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT V6.1 (Bruker, 2000)' _computing_cell_refinement 'SMART-NT V6.1 (Bruker, 2000)' _computing_data_reduction 'SAINT-NT V6.02 (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0963P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881; 1232 Friedel pairs' _refine_ls_abs_structure_Flack 0.14(13) _refine_ls_number_reflns 2632 _refine_ls_number_parameters 147 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1587 _refine_ls_wR_factor_gt 0.1510 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.77508(19) 0.13766(8) 0.89969(7) 0.0195(2) Uani 1 1 d . . . O1 O 0.1156(7) 0.1877(2) 0.5366(3) 0.0302(6) Uani 1 1 d . . . N1 N 0.7204(7) -0.0578(2) 0.8234(3) 0.0179(6) Uani 1 1 d . . . C1 C 0.7366(10) -0.2503(3) 0.7866(4) 0.0254(7) Uani 1 1 d . . . H1A H 0.9849 -0.2490 0.8148 0.038 Uiso 1 1 calc R . . H1B H 0.6949 -0.3006 0.7146 0.038 Uiso 1 1 calc R . . H1C H 0.6059 -0.2739 0.8576 0.038 Uiso 1 1 calc R . . C2 C 0.6207(9) -0.1393(3) 0.7447(3) 0.0186(6) Uani 1 1 d . . . C3 C 0.4150(9) -0.1236(3) 0.6299(3) 0.0217(7) Uani 1 1 d . . . H3 H 0.3427 -0.1834 0.5773 0.026 Uiso 1 1 calc R . . C4 C 0.3189(9) -0.0208(3) 0.5943(3) 0.0201(7) Uani 1 1 d . . . H4 H 0.1843 -0.0084 0.5154 0.024 Uiso 1 1 calc R . . C5 C 0.4193(8) 0.0659(3) 0.6744(3) 0.0153(6) Uani 1 1 d . . . C6 C 0.6208(9) 0.0414(2) 0.7873(3) 0.0156(6) Uani 1 1 d . . . C7 C 0.3034(9) 0.1751(3) 0.6351(3) 0.0193(6) Uani 1 1 d . . . C8 C 0.4161(8) 0.2681(2) 0.7163(3) 0.0171(7) Uani 1 1 d . . . C9 C 0.6192(8) 0.2588(3) 0.8328(3) 0.0166(6) Uani 1 1 d . . . C10 C 0.3100(9) 0.3706(3) 0.6738(3) 0.0211(7) Uani 1 1 d . . . H10 H 0.1719 0.3779 0.5947 0.025 Uiso 1 1 calc R . . C11 C 0.4016(9) 0.4610(3) 0.7444(4) 0.0248(8) Uani 1 1 d . . . H11 H 0.3284 0.5303 0.7139 0.030 Uiso 1 1 calc R . . C12 C 0.6022(9) 0.4510(3) 0.8608(4) 0.0232(7) Uani 1 1 d . . . H12 H 0.6621 0.5134 0.9106 0.028 Uiso 1 1 calc R . . C13 C 0.7136(9) 0.3511(3) 0.9038(3) 0.0218(7) Uani 1 1 d . . . H13 H 0.8556 0.3448 0.9822 0.026 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 0.0275(4) 0.0142(3) 0.0150(3) -0.0008(3) -0.0084(3) -0.0004(4) O1 0.0426(14) 0.0196(12) 0.0243(13) 0.0015(11) -0.0210(11) 0.0012(11) N1 0.0207(13) 0.0141(12) 0.0175(14) 0.0011(11) -0.0069(11) -0.0002(10) C1 0.0333(19) 0.0129(14) 0.0285(17) 0.0010(14) -0.0057(14) 0.0013(14) C2 0.0242(15) 0.0151(14) 0.0161(15) -0.0001(12) -0.0006(12) -0.0011(13) C3 0.0252(17) 0.0185(17) 0.0208(17) -0.0028(13) -0.0019(14) -0.0038(13) C4 0.0253(15) 0.0196(15) 0.0144(14) 0.0002(12) -0.0044(13) -0.0013(13) C5 0.0181(14) 0.0135(14) 0.0136(15) -0.0007(11) -0.0026(11) -0.0013(12) C6 0.0173(15) 0.0159(16) 0.0125(14) -0.0019(12) -0.0048(12) -0.0013(11) C7 0.0200(14) 0.0174(15) 0.0202(15) 0.0011(12) -0.0001(12) -0.0013(12) C8 0.0185(14) 0.0155(17) 0.0165(15) 0.0011(11) -0.0023(12) 0.0002(12) C9 0.0161(14) 0.0172(16) 0.0159(15) 0.0008(12) -0.0022(12) 0.0020(13) C10 0.0241(16) 0.0175(16) 0.0212(18) 0.0039(13) -0.0003(14) 0.0037(13) C11 0.0298(17) 0.0131(16) 0.0307(19) 0.0019(13) -0.0018(15) 0.0028(13) C12 0.0293(17) 0.0134(15) 0.0262(19) -0.0031(12) -0.0007(14) -0.0020(13) C13 0.0261(16) 0.0212(17) 0.0176(17) -0.0018(13) -0.0016(13) -0.0022(14) _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 C9 1.741(3) . ? S1 C6 1.743(3) . ? O1 C7 1.219(4) . ? N1 C6 1.333(4) . ? N1 C2 1.338(4) . ? C1 C2 1.500(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.396(5) . ? C3 C4 1.370(5) . ? C3 H3 0.9500 . ? C4 C5 1.396(5) . ? C4 H4 0.9500 . ? C5 C6 1.391(4) . ? C5 C7 1.472(4) . ? C7 C8 1.475(5) . ? C8 C10 1.395(5) . ? C8 C9 1.397(5) . ? C9 C13 1.394(5) . ? C10 C11 1.370(5) . ? C10 H10 0.9500 . ? C11 C12 1.392(5) . ? C11 H11 0.9500 . ? C12 C13 1.373(5) . ? C12 H12 0.9500 . ? C13 H13 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 C9 S1 C6 103.40(18) . . ? C6 N1 C2 117.4(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 122.5(3) . . ? N1 C2 C1 116.7(3) . . ? C3 C2 C1 120.8(3) . . ? C4 C3 C2 119.0(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 116.7(3) . . ? C6 C5 C7 124.9(3) . . ? C4 C5 C7 118.4(3) . . ? N1 C6 C5 124.7(3) . . ? N1 C6 S1 111.4(2) . . ? C5 C6 S1 123.9(3) . . ? O1 C7 C5 119.9(3) . . ? O1 C7 C8 120.8(3) . . ? C5 C7 C8 119.3(3) . . ? C10 C8 C9 118.8(3) . . ? C10 C8 C7 117.6(3) . . ? C9 C8 C7 123.7(3) . . ? C13 C9 C8 119.9(3) . . ? C13 C9 S1 115.3(3) . . ? C8 C9 S1 124.8(3) . . ? C11 C10 C8 121.1(3) . . ? C11 C10 H10 119.5 . . ? C8 C10 H10 119.5 . . ? C10 C11 C12 119.8(3) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 120.1(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C9 120.2(3) . . ? C12 C13 H13 119.9 . . ? C9 C13 H13 119.9 . . ? 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 C6 N1 C2 C3 -1.2(5) . . . . ? C6 N1 C2 C1 179.7(3) . . . . ? N1 C2 C3 C4 1.9(5) . . . . ? C1 C2 C3 C4 -179.1(3) . . . . ? C2 C3 C4 C5 -1.7(5) . . . . ? C3 C4 C5 C6 1.1(5) . . . . ? C3 C4 C5 C7 -178.3(3) . . . . ? C2 N1 C6 C5 0.5(5) . . . . ? C2 N1 C6 S1 -179.5(2) . . . . ? C4 C5 C6 N1 -0.4(5) . . . . ? C7 C5 C6 N1 178.9(3) . . . . ? C4 C5 C6 S1 179.6(2) . . . . ? C7 C5 C6 S1 -1.1(5) . . . . ? C9 S1 C6 N1 179.5(2) . . . . ? C9 S1 C6 C5 -0.5(3) . . . . ? C6 C5 C7 O1 -177.1(3) . . . . ? C4 C5 C7 O1 2.2(5) . . . . ? C6 C5 C7 C8 2.7(5) . . . . ? C4 C5 C7 C8 -178.0(3) . . . . ? O1 C7 C8 C10 -2.2(5) . . . . ? C5 C7 C8 C10 178.0(3) . . . . ? O1 C7 C8 C9 177.3(3) . . . . ? C5 C7 C8 C9 -2.5(5) . . . . ? C10 C8 C9 C13 -0.4(5) . . . . ? C7 C8 C9 C13 -179.9(3) . . . . ? C10 C8 C9 S1 -179.7(2) . . . . ? C7 C8 C9 S1 0.8(5) . . . . ? C6 S1 C9 C13 -178.7(3) . . . . ? C6 S1 C9 C8 0.7(3) . . . . ? C9 C8 C10 C11 0.0(5) . . . . ? C7 C8 C10 C11 179.5(3) . . . . ? C8 C10 C11 C12 -0.4(6) . . . . ? C10 C11 C12 C13 1.2(6) . . . . ? C11 C12 C13 C9 -1.7(5) . . . . ? C8 C9 C13 C12 1.3(5) . . . . ? S1 C9 C13 C12 -179.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.11 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.907 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.125