# Electronic Supplementary Material (ESI) for Chemical Science # 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_120809_s2_2304 _database_code_depnum_ccdc_archive 'CCDC 906804' #TrackingRef '14785_web_deposit_cif_file_0_BoLiu_1350627676.3k.cif' _audit_creation_date 2012-08-09 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C14 H12 N2' _chemical_formula_sum 'C14 H12 N2' _chemical_formula_weight 208.26 _chemical_absolute_configuration unk _chemical_melting_point ? _chemical_oxdiff_formula C12H10N4O3 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' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_length_a 12.1824(8) _cell_length_b 7.5600(4) _cell_length_c 12.3739(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.815(6) _cell_angle_gamma 90.00 _cell_volume 1090.89(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1348 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.1637 _cell_measurement_theta_min 3.1903 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.98431 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.30 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0143 _diffrn_reflns_av_unetI/netI 0.0332 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4512 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.20 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -70.00 -44.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -178.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -5.00 85.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 20.0174 37.0000 -180.0000 90 #__ type_ start__ end____ width___ exp.time_ 3 omega -41.00 58.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 20.0174 -19.0000 150.0000 99 #__ type_ start__ end____ width___ exp.time_ 4 omega -52.00 -27.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 20.0174 -37.0000 30.0000 25 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0099567000 _diffrn_orient_matrix_UB_12 -0.0260164000 _diffrn_orient_matrix_UB_13 -0.0571182000 _diffrn_orient_matrix_UB_21 -0.0573520000 _diffrn_orient_matrix_UB_22 0.0307910000 _diffrn_orient_matrix_UB_23 -0.0125221000 _diffrn_orient_matrix_UB_31 0.0177119000 _diffrn_orient_matrix_UB_32 0.0846996000 _diffrn_orient_matrix_UB_33 -0.0129528000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2521 _reflns_number_total 3195 _reflns_odcompleteness_completeness 99.79 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.117 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.027 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(3) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 291 _refine_ls_number_reflns 3195 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0444 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.0102P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1024 _refine_ls_wR_factor_ref 0.1145 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.19531(17) 0.3158(3) 0.66556(17) 0.0528(6) Uani 1 1 d . . . N2 N 0.2102(2) 0.3213(4) 0.43606(19) 0.0760(8) Uani 1 1 d . . . N3 N 0.55064(16) 0.2633(3) 0.15397(17) 0.0500(6) Uani 1 1 d . . . N4 N 0.51963(19) 0.4011(4) 0.36957(19) 0.0703(7) Uani 1 1 d . . . C1 C 0.1134(2) 0.2404(4) 0.5747(2) 0.0505(7) Uani 1 1 d . . . C2 C 0.0246(2) 0.1799(4) 0.6102(2) 0.0570(7) Uani 1 1 d . . . H2 H -0.0407 0.1235 0.5656 0.068 Uiso 1 1 calc R . . C3 C 0.0490(2) 0.2176(4) 0.7266(2) 0.0543(7) Uani 1 1 d . . . C4 C 0.1555(2) 0.3023(4) 0.7584(2) 0.0525(7) Uani 1 1 d . . . C5 C 0.2046(2) 0.3622(4) 0.8686(2) 0.0637(8) Uani 1 1 d . . . H5 H 0.2758 0.4175 0.8894 0.076 Uiso 1 1 calc R . . C6 C 0.1441(3) 0.3366(5) 0.9449(2) 0.0742(9) Uani 1 1 d . . . H6 H 0.1745 0.3778 1.0184 0.089 Uiso 1 1 calc R . . C7 C 0.0387(3) 0.2511(5) 0.9160(3) 0.0777(10) Uani 1 1 d . . . H7 H 0.0001 0.2351 0.9700 0.093 Uiso 1 1 calc R . . C8 C -0.0085(2) 0.1901(5) 0.8083(3) 0.0706(9) Uani 1 1 d . . . H8 H -0.0784 0.1308 0.7895 0.085 Uiso 1 1 calc R . . C9 C 0.1223(2) 0.2386(4) 0.4582(2) 0.0533(7) Uani 1 1 d . . . C10 C 0.0382(3) 0.1565(4) 0.3737(2) 0.0712(9) Uani 1 1 d . . . H10 H -0.0238 0.1033 0.3903 0.085 Uiso 1 1 calc R . . C11 C 0.0461(3) 0.1534(5) 0.2655(3) 0.0862(11) Uani 1 1 d . . . H11 H -0.0111 0.1007 0.2079 0.103 Uiso 1 1 calc R . . C12 C 0.1387(3) 0.2284(6) 0.2438(3) 0.0921(12) Uani 1 1 d . . . H12 H 0.1488 0.2225 0.1723 0.111 Uiso 1 1 calc R . . C13 C 0.2170(3) 0.3133(6) 0.3307(3) 0.0961(14) Uani 1 1 d . . . H13 H 0.2787 0.3689 0.3149 0.115 Uiso 1 1 calc R . . C14 C 0.3118(2) 0.3702(5) 0.6735(2) 0.0738(9) Uani 1 1 d . . . H14A H 0.3445 0.2894 0.6316 0.111 Uiso 1 1 calc R . . H14B H 0.3570 0.3700 0.7513 0.111 Uiso 1 1 calc R . . H14C H 0.3109 0.4872 0.6431 0.111 Uiso 1 1 calc R . . C15 C 0.6342(2) 0.3383(4) 0.2443(2) 0.0515(7) Uani 1 1 d . . . C16 C 0.7269(2) 0.3792(4) 0.2090(2) 0.0588(8) Uani 1 1 d . . . H16 H 0.7945 0.4300 0.2532 0.071 Uiso 1 1 calc R . . C17 C 0.7031(2) 0.3314(4) 0.0935(2) 0.0543(7) Uani 1 1 d . . . C18 C 0.5926(2) 0.2560(4) 0.0625(2) 0.0493(7) Uani 1 1 d . . . C19 C 0.5432(2) 0.1863(4) -0.0447(2) 0.0600(8) Uani 1 1 d . . . H19 H 0.4705 0.1360 -0.0641 0.072 Uiso 1 1 calc R . . C20 C 0.6062(3) 0.1947(4) -0.1213(3) 0.0708(9) Uani 1 1 d . . . H20 H 0.5755 0.1491 -0.1935 0.085 Uiso 1 1 calc R . . C21 C 0.7151(3) 0.2704(5) -0.0918(3) 0.0734(9) Uani 1 1 d . . . H21 H 0.7557 0.2744 -0.1449 0.088 Uiso 1 1 calc R . . C22 C 0.7637(2) 0.3393(4) 0.0137(3) 0.0655(9) Uani 1 1 d . . . H22 H 0.8362 0.3906 0.0318 0.079 Uiso 1 1 calc R . . C23 C 0.6222(2) 0.3608(4) 0.3579(2) 0.0543(7) Uani 1 1 d . . . C24 C 0.7186(3) 0.3436(5) 0.4503(2) 0.0722(9) Uani 1 1 d . . . H24 H 0.7894 0.3173 0.4398 0.087 Uiso 1 1 calc R . . C25 C 0.7088(3) 0.3656(5) 0.5566(3) 0.0854(11) Uani 1 1 d . . . H25 H 0.7727 0.3538 0.6192 0.102 Uiso 1 1 calc R . . C26 C 0.6039(3) 0.4052(5) 0.5700(3) 0.0841(11) Uani 1 1 d . . . H26 H 0.5946 0.4199 0.6415 0.101 Uiso 1 1 calc R . . C27 C 0.5133(3) 0.4223(6) 0.4749(3) 0.0834(11) Uani 1 1 d . . . H27 H 0.4423 0.4508 0.4841 0.100 Uiso 1 1 calc R . . C28 C 0.4403(2) 0.1901(4) 0.1547(2) 0.0677(9) Uani 1 1 d . . . H28A H 0.3816 0.2777 0.1283 0.102 Uiso 1 1 calc R . . H28B H 0.4433 0.1556 0.2302 0.102 Uiso 1 1 calc R . . H28C H 0.4232 0.0886 0.1060 0.102 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 0.0442(12) 0.0538(16) 0.0559(13) -0.0020(12) 0.0071(10) -0.0042(11) N2 0.0673(16) 0.103(2) 0.0556(15) -0.0005(15) 0.0138(12) -0.0191(17) N3 0.0425(12) 0.0497(13) 0.0531(13) 0.0014(11) 0.0062(10) -0.0067(11) N4 0.0597(15) 0.090(2) 0.0583(14) 0.0022(14) 0.0130(12) 0.0026(15) C1 0.0455(14) 0.0436(16) 0.0574(16) -0.0022(13) 0.0067(12) 0.0001(14) C2 0.0450(15) 0.0584(18) 0.0627(18) -0.0064(15) 0.0079(13) -0.0030(15) C3 0.0466(15) 0.0538(19) 0.0607(17) 0.0012(15) 0.0128(13) 0.0053(14) C4 0.0516(16) 0.0476(17) 0.0557(16) 0.0006(14) 0.0114(13) 0.0053(13) C5 0.0642(17) 0.064(2) 0.0558(17) 0.0015(16) 0.0060(14) -0.0045(17) C6 0.078(2) 0.086(3) 0.0528(17) 0.0058(18) 0.0106(16) 0.011(2) C7 0.072(2) 0.099(3) 0.0643(19) 0.014(2) 0.0231(16) 0.012(2) C8 0.0512(17) 0.082(2) 0.078(2) 0.0102(19) 0.0185(16) 0.0027(17) C9 0.0532(16) 0.0506(17) 0.0517(15) 0.0037(14) 0.0080(13) -0.0005(15) C10 0.076(2) 0.068(2) 0.0618(19) -0.0017(17) 0.0079(15) -0.0167(18) C11 0.105(3) 0.083(3) 0.059(2) -0.005(2) 0.0056(18) -0.024(2) C12 0.108(3) 0.111(3) 0.0527(19) 0.008(2) 0.0166(19) -0.006(3) C13 0.083(2) 0.142(4) 0.061(2) 0.001(2) 0.0171(17) -0.029(2) C14 0.0591(18) 0.090(3) 0.0672(18) -0.0048(19) 0.0110(14) -0.0293(19) C15 0.0424(14) 0.0503(17) 0.0554(16) -0.0013(14) 0.0041(12) -0.0002(14) C16 0.0433(15) 0.060(2) 0.0661(18) -0.0066(16) 0.0056(13) -0.0085(15) C17 0.0470(15) 0.0507(17) 0.0641(17) -0.0013(15) 0.0144(13) 0.0018(14) C18 0.0506(15) 0.0397(15) 0.0542(16) -0.0018(13) 0.0097(12) 0.0031(14) C19 0.0596(17) 0.0507(17) 0.0634(18) -0.0005(15) 0.0077(14) -0.0011(15) C20 0.080(2) 0.065(2) 0.0652(19) -0.0060(17) 0.0172(17) 0.0091(19) C21 0.071(2) 0.081(2) 0.075(2) -0.0003(19) 0.0320(17) 0.013(2) C22 0.0521(16) 0.069(2) 0.078(2) -0.0010(18) 0.0224(16) 0.0038(16) C23 0.0553(16) 0.0497(17) 0.0539(16) 0.0005(14) 0.0097(13) -0.0035(15) C24 0.0615(18) 0.084(2) 0.0618(18) -0.0076(19) 0.0036(14) -0.0005(18) C25 0.088(3) 0.092(3) 0.059(2) -0.004(2) -0.0053(17) -0.007(2) C26 0.093(2) 0.100(3) 0.0570(19) -0.0129(19) 0.0183(18) -0.012(2) C27 0.079(2) 0.109(3) 0.067(2) -0.003(2) 0.0277(17) -0.003(2) C28 0.0502(16) 0.078(2) 0.0693(19) 0.0031(18) 0.0083(14) -0.0162(17) _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 C1 1.391(3) . ? N1 C4 1.375(3) . ? N1 C14 1.453(3) . ? N2 C9 1.336(3) . ? N2 C13 1.332(4) . ? N3 C15 1.396(3) . ? N3 C18 1.371(3) . ? N3 C28 1.456(3) . ? N4 C23 1.334(3) . ? N4 C27 1.337(3) . ? C1 C2 1.359(4) . ? C1 C9 1.476(3) . ? C2 H2 0.9300 . ? C2 C3 1.414(4) . ? C3 C4 1.398(3) . ? C3 C8 1.402(4) . ? C4 C5 1.396(4) . ? C5 H5 0.9300 . ? C5 C6 1.369(4) . ? C6 H6 0.9300 . ? C6 C7 1.388(4) . ? C7 H7 0.9300 . ? C7 C8 1.369(4) . ? C8 H8 0.9300 . ? C9 C10 1.381(4) . ? C10 H10 0.9300 . ? C10 C11 1.369(4) . ? C11 H11 0.9300 . ? C11 C12 1.357(4) . ? C12 H12 0.9300 . ? C12 C13 1.372(5) . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.358(3) . ? C15 C23 1.465(3) . ? C16 H16 0.9300 . ? C16 C17 1.421(4) . ? C17 C18 1.409(3) . ? C17 C22 1.395(4) . ? C18 C19 1.392(4) . ? C19 H19 0.9300 . ? C19 C20 1.383(4) . ? C20 H20 0.9300 . ? C20 C21 1.393(4) . ? C21 H21 0.9300 . ? C21 C22 1.371(4) . ? C22 H22 0.9300 . ? C23 C24 1.388(3) . ? C24 H24 0.9300 . ? C24 C25 1.364(4) . ? C25 H25 0.9300 . ? C25 C26 1.369(4) . ? C26 H26 0.9300 . ? C26 C27 1.367(4) . ? C27 H27 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 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 C1 N1 C14 129.0(2) . . ? C4 N1 C1 107.5(2) . . ? C4 N1 C14 122.6(2) . . ? C13 N2 C9 117.4(3) . . ? C15 N3 C28 127.6(2) . . ? C18 N3 C15 108.5(2) . . ? C18 N3 C28 123.7(2) . . ? C23 N4 C27 116.9(3) . . ? N1 C1 C9 123.7(2) . . ? C2 C1 N1 109.2(2) . . ? C2 C1 C9 127.0(2) . . ? C1 C2 H2 126.0 . . ? C1 C2 C3 108.0(2) . . ? C3 C2 H2 126.0 . . ? C4 C3 C2 106.5(2) . . ? C4 C3 C8 118.8(3) . . ? C8 C3 C2 134.7(3) . . ? N1 C4 C3 108.8(2) . . ? N1 C4 C5 129.6(3) . . ? C5 C4 C3 121.6(3) . . ? C4 C5 H5 121.2 . . ? C6 C5 C4 117.6(3) . . ? C6 C5 H5 121.2 . . ? C5 C6 H6 119.0 . . ? C5 C6 C7 122.0(3) . . ? C7 C6 H6 119.0 . . ? C6 C7 H7 119.8 . . ? C8 C7 C6 120.3(3) . . ? C8 C7 H7 119.8 . . ? C3 C8 H8 120.2 . . ? C7 C8 C3 119.6(3) . . ? C7 C8 H8 120.2 . . ? N2 C9 C1 119.1(2) . . ? N2 C9 C10 121.1(3) . . ? C10 C9 C1 119.8(3) . . ? C9 C10 H10 119.9 . . ? C11 C10 C9 120.2(3) . . ? C11 C10 H10 119.9 . . ? C10 C11 H11 120.6 . . ? C12 C11 C10 118.9(3) . . ? C12 C11 H11 120.6 . . ? C11 C12 H12 121.0 . . ? C11 C12 C13 118.0(3) . . ? C13 C12 H12 121.0 . . ? N2 C13 C12 124.2(3) . . ? N2 C13 H13 117.9 . . ? C12 C13 H13 117.9 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 C23 124.3(2) . . ? C16 C15 N3 108.5(2) . . ? C16 C15 C23 127.2(2) . . ? C15 C16 H16 125.7 . . ? C15 C16 C17 108.6(2) . . ? C17 C16 H16 125.7 . . ? C18 C17 C16 106.0(2) . . ? C22 C17 C16 134.9(3) . . ? C22 C17 C18 119.0(3) . . ? N3 C18 C17 108.3(2) . . ? N3 C18 C19 129.8(2) . . ? C19 C18 C17 121.8(3) . . ? C18 C19 H19 121.2 . . ? C20 C19 C18 117.6(3) . . ? C20 C19 H19 121.2 . . ? C19 C20 H20 119.5 . . ? C19 C20 C21 121.0(3) . . ? C21 C20 H20 119.5 . . ? C20 C21 H21 119.3 . . ? C22 C21 C20 121.5(3) . . ? C22 C21 H21 119.3 . . ? C17 C22 H22 120.5 . . ? C21 C22 C17 119.1(3) . . ? C21 C22 H22 120.5 . . ? N4 C23 C15 119.1(2) . . ? N4 C23 C24 121.9(3) . . ? C24 C23 C15 119.0(3) . . ? C23 C24 H24 120.2 . . ? C25 C24 C23 119.6(3) . . ? C25 C24 H24 120.2 . . ? C24 C25 H25 120.4 . . ? C24 C25 C26 119.3(3) . . ? C26 C25 H25 120.4 . . ? C25 C26 H26 121.1 . . ? C27 C26 C25 117.7(3) . . ? C27 C26 H26 121.1 . . ? N4 C27 C26 124.6(3) . . ? N4 C27 H27 117.7 . . ? C26 C27 H27 117.7 . . ? N3 C28 H28A 109.5 . . ? N3 C28 H28B 109.5 . . ? N3 C28 H28C 109.5 . . ? H28A C28 H28B 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? data_120809_s4_2230 _database_code_depnum_ccdc_archive 'CCDC 906805' #TrackingRef '14786_web_deposit_cif_file_1_BoLiu_1350627676.3o.cif' _audit_creation_date 2012-08-09 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H17 N5 O2' _chemical_formula_sum 'C15 H17 N5 O2' _chemical_formula_weight 299.34 _chemical_melting_point ? _chemical_oxdiff_formula C12H10N4O3 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 10.8034(5) _cell_length_b 6.9959(3) _cell_length_c 19.4702(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.269(5) _cell_angle_gamma 90.00 _cell_volume 1437.95(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1431 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.0419 _cell_measurement_theta_min 2.9058 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.76276 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.32 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_unetI/netI 0.0469 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 6064 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.10 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -10.00 24.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -99.0000 -180.0000 34 #__ type_ start__ end____ width___ exp.time_ 2 omega -48.00 42.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 -37.0000 120.0000 90 #__ type_ start__ end____ width___ exp.time_ 3 omega -22.00 81.00 1.0000 8.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 19.0000 -39.0000 103 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0277287000 _diffrn_orient_matrix_UB_12 0.0137805000 _diffrn_orient_matrix_UB_13 0.0295449000 _diffrn_orient_matrix_UB_21 -0.0605378000 _diffrn_orient_matrix_UB_22 -0.0209885000 _diffrn_orient_matrix_UB_23 -0.0210568000 _diffrn_orient_matrix_UB_31 0.0090527000 _diffrn_orient_matrix_UB_32 -0.0981865000 _diffrn_orient_matrix_UB_33 0.0086414000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1973 _reflns_number_total 2938 _reflns_odcompleteness_completeness 99.81 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.203 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.073 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 2938 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0546 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0705P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1281 _refine_ls_wR_factor_ref 0.1519 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.51363(13) 0.7261(2) 0.04789(9) 0.0625(5) Uani 1 1 d . . . O2 O 0.90969(14) 0.7945(2) 0.00302(8) 0.0602(5) Uani 1 1 d . . . N1 N 0.71264(15) 0.7617(2) 0.02682(9) 0.0428(4) Uani 1 1 d . . . N2 N 0.67896(14) 0.7077(2) 0.14114(9) 0.0374(4) Uani 1 1 d . . . N3 N 1.00758(14) 0.76605(19) 0.16440(8) 0.0333(4) Uani 1 1 d . . . N4 N 0.86830(14) 0.71208(19) 0.23313(9) 0.0341(4) Uani 1 1 d . . . N5 N 1.21037(15) 0.7219(2) 0.29268(9) 0.0403(4) Uani 1 1 d . . . C1 C 0.62755(18) 0.7315(2) 0.07115(12) 0.0409(5) Uani 1 1 d . . . C2 C 0.84504(19) 0.7728(2) 0.04704(11) 0.0386(5) Uani 1 1 d . . . C3 C 0.88835(17) 0.7567(2) 0.12146(11) 0.0332(4) Uani 1 1 d . . . C4 C 0.80763(17) 0.7250(2) 0.16551(10) 0.0320(4) Uani 1 1 d . . . C5 C 0.99058(17) 0.7384(2) 0.23106(10) 0.0315(4) Uani 1 1 d . . . C6 C 0.6537(2) 0.7855(3) -0.04783(12) 0.0649(7) Uani 1 1 d . . . H6A H 0.6063 0.6728 -0.0647 0.097 Uiso 1 1 calc R . . H6B H 0.7183 0.8056 -0.0741 0.097 Uiso 1 1 calc R . . H6C H 0.5979 0.8939 -0.0535 0.097 Uiso 1 1 calc R . . C7 C 0.59567(17) 0.6590(3) 0.18900(11) 0.0445(5) Uani 1 1 d . . . H7A H 0.6434 0.5854 0.2280 0.053 Uiso 1 1 calc R . . H7B H 0.5272 0.5790 0.1642 0.053 Uiso 1 1 calc R . . C8 C 0.5405(2) 0.8303(3) 0.21735(14) 0.0696(8) Uani 1 1 d . . . H8A H 0.4910 0.9021 0.1792 0.104 Uiso 1 1 calc R . . H8B H 0.6076 0.9091 0.2427 0.104 Uiso 1 1 calc R . . H8C H 0.4874 0.7896 0.2484 0.104 Uiso 1 1 calc R . . C9 C 1.12415(17) 0.8149(3) 0.13979(11) 0.0440(5) Uani 1 1 d . . . H9A H 1.1815 0.8838 0.1766 0.053 Uiso 1 1 calc R . . H9B H 1.1027 0.8982 0.0992 0.053 Uiso 1 1 calc R . . C10 C 1.18951(19) 0.6390(3) 0.12045(13) 0.0591(6) Uani 1 1 d . . . H10A H 1.1325 0.5696 0.0845 0.089 Uiso 1 1 calc R . . H10B H 1.2146 0.5593 0.1612 0.089 Uiso 1 1 calc R . . H10C H 1.2631 0.6760 0.1034 0.089 Uiso 1 1 calc R . . C11 C 1.08854(17) 0.7387(2) 0.29635(10) 0.0325(4) Uani 1 1 d . . . C12 C 1.05006(19) 0.7535(2) 0.35961(11) 0.0397(5) Uani 1 1 d . . . H12 H 0.9644 0.7626 0.3602 0.048 Uiso 1 1 calc R . . C13 C 1.1393(2) 0.7546(3) 0.42129(12) 0.0483(5) Uani 1 1 d . . . H13 H 1.1150 0.7649 0.4642 0.058 Uiso 1 1 calc R . . C14 C 1.2654(2) 0.7403(2) 0.41882(12) 0.0468(6) Uani 1 1 d . . . H14 H 1.3283 0.7424 0.4596 0.056 Uiso 1 1 calc R . . C15 C 1.29480(19) 0.7229(3) 0.35372(12) 0.0442(5) Uani 1 1 d . . . H15 H 1.3799 0.7109 0.3521 0.053 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 0.0298(8) 0.0956(12) 0.0555(11) -0.0032(8) -0.0059(8) 0.0014(7) O2 0.0474(9) 0.0998(11) 0.0344(9) 0.0033(8) 0.0107(7) -0.0026(8) N1 0.0345(9) 0.0564(10) 0.0339(10) -0.0014(8) -0.0011(8) 0.0032(7) N2 0.0262(8) 0.0470(9) 0.0374(10) 0.0019(8) 0.0036(7) 0.0006(6) N3 0.0260(8) 0.0430(9) 0.0309(9) 0.0001(7) 0.0057(7) -0.0005(6) N4 0.0282(8) 0.0410(8) 0.0322(9) 0.0004(7) 0.0041(7) -0.0006(6) N5 0.0303(9) 0.0520(9) 0.0364(10) 0.0012(8) 0.0023(7) 0.0014(7) C1 0.0308(11) 0.0473(11) 0.0423(12) -0.0040(10) 0.0027(9) 0.0029(8) C2 0.0344(11) 0.0464(11) 0.0342(11) -0.0004(9) 0.0058(9) 0.0016(8) C3 0.0272(10) 0.0384(10) 0.0331(11) 0.0013(8) 0.0043(8) 0.0005(7) C4 0.0275(10) 0.0327(9) 0.0342(11) 0.0014(8) 0.0025(8) 0.0022(7) C5 0.0301(10) 0.0325(9) 0.0309(10) 0.0002(8) 0.0040(8) 0.0003(7) C6 0.0500(15) 0.1047(18) 0.0339(13) -0.0011(13) -0.0046(11) 0.0070(12) C7 0.0324(11) 0.0520(11) 0.0506(13) 0.0049(10) 0.0118(9) -0.0037(8) C8 0.0745(18) 0.0671(14) 0.080(2) -0.0081(14) 0.0440(16) -0.0013(12) C9 0.0318(11) 0.0619(12) 0.0388(12) 0.0042(10) 0.0085(9) -0.0072(9) C10 0.0433(13) 0.0822(15) 0.0550(15) 0.0000(13) 0.0174(11) 0.0111(11) C11 0.0323(10) 0.0309(9) 0.0323(11) 0.0010(8) 0.0026(8) 0.0000(7) C12 0.0341(11) 0.0501(11) 0.0347(11) 0.0010(9) 0.0070(9) 0.0001(8) C13 0.0477(13) 0.0626(13) 0.0339(12) -0.0017(10) 0.0069(10) -0.0039(9) C14 0.0434(12) 0.0527(12) 0.0377(12) 0.0023(10) -0.0062(10) -0.0045(9) C15 0.0298(10) 0.0566(12) 0.0431(13) 0.0020(10) 0.0005(9) -0.0002(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.218(2) . ? O2 C2 1.225(2) . ? N1 C1 1.404(3) . ? N1 C2 1.403(2) . ? N1 C6 1.467(3) . ? N2 C1 1.368(3) . ? N2 C4 1.375(2) . ? N2 C7 1.466(2) . ? N3 C3 1.380(2) . ? N3 C5 1.363(3) . ? N3 C9 1.480(2) . ? N4 C4 1.343(2) . ? N4 C5 1.343(2) . ? N5 C11 1.338(2) . ? N5 C15 1.336(3) . ? C2 C3 1.429(3) . ? C3 C4 1.365(3) . ? C5 C11 1.471(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.495(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.506(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.385(3) . ? C12 H12 0.9300 . ? C12 C13 1.371(3) . ? C13 H13 0.9300 . ? C13 C14 1.377(3) . ? C14 H14 0.9300 . ? C14 C15 1.376(3) . ? C15 H15 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 C1 N1 C6 115.02(17) . . ? C2 N1 C1 126.70(18) . . ? C2 N1 C6 118.28(18) . . ? C1 N2 C4 119.97(18) . . ? C1 N2 C7 119.15(16) . . ? C4 N2 C7 120.86(17) . . ? C3 N3 C9 124.32(16) . . ? C5 N3 C3 105.84(15) . . ? C5 N3 C9 129.61(16) . . ? C5 N4 C4 103.87(16) . . ? C15 N5 C11 116.45(18) . . ? O1 C1 N1 121.2(2) . . ? O1 C1 N2 122.1(2) . . ? N2 C1 N1 116.76(17) . . ? O2 C2 N1 120.6(2) . . ? O2 C2 C3 127.36(19) . . ? N1 C2 C3 112.01(17) . . ? N3 C3 C2 132.28(18) . . ? C4 C3 N3 105.41(17) . . ? C4 C3 C2 122.32(18) . . ? N4 C4 N2 125.39(18) . . ? N4 C4 C3 112.52(17) . . ? C3 C4 N2 122.09(19) . . ? N3 C5 C11 127.23(17) . . ? N4 C5 N3 112.37(17) . . ? N4 C5 C11 120.40(18) . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7A 108.9 . . ? N2 C7 H7B 108.9 . . ? N2 C7 C8 113.28(16) . . ? H7A C7 H7B 107.7 . . ? C8 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 H9A 109.3 . . ? N3 C9 H9B 109.3 . . ? N3 C9 C10 111.63(15) . . ? H9A C9 H9B 108.0 . . ? C10 C9 H9A 109.3 . . ? C10 C9 H9B 109.3 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N5 C11 C5 119.26(18) . . ? N5 C11 C12 122.59(18) . . ? C12 C11 C5 118.15(17) . . ? C11 C12 H12 120.3 . . ? C13 C12 C11 119.43(19) . . ? C13 C12 H12 120.3 . . ? C12 C13 H13 120.5 . . ? C12 C13 C14 119.1(2) . . ? C14 C13 H13 120.5 . . ? C13 C14 H14 121.2 . . ? C15 C14 C13 117.6(2) . . ? C15 C14 H14 121.2 . . ? N5 C15 C14 124.90(19) . . ? N5 C15 H15 117.5 . . ? C14 C15 H15 117.5 . . ? data_120809_s5_2128 _database_code_depnum_ccdc_archive 'CCDC 906806' #TrackingRef '14787_web_deposit_cif_file_2_BoLiu_1350627676.3f.cif' _audit_creation_date 2012-08-09 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H11 N O S' _chemical_formula_sum 'C16 H11 N O S' _chemical_formula_weight 265.32 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula C12H10N4O3 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' _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_H-M_alt 'P n a 21' _space_group_name_Hall 'P 2c -2n' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z+1/2' 3 '-x+1/2, y+1/2, z+1/2' 4 'x+1/2, -y+1/2, z' _cell_length_a 23.0013(19) _cell_length_b 5.0777(3) _cell_length_c 11.1540(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1302.71(18) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1043 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.8656 _cell_measurement_theta_min 3.2177 _exptl_absorpt_coefficient_mu 0.238 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.97294 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_unetI/netI 0.0395 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 3695 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.54 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -15.00 24.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -99.0000 -180.0000 39 #__ type_ start__ end____ width___ exp.time_ 2 omega -30.00 7.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -37.0000 120.0000 37 #__ type_ start__ end____ width___ exp.time_ 3 omega -41.00 40.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 -57.0000 60.0000 81 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0276012000 _diffrn_orient_matrix_UB_12 -0.0097594000 _diffrn_orient_matrix_UB_13 0.0280145000 _diffrn_orient_matrix_UB_21 -0.0137401000 _diffrn_orient_matrix_UB_22 0.0127094000 _diffrn_orient_matrix_UB_23 -0.0566456000 _diffrn_orient_matrix_UB_31 0.0006700000 _diffrn_orient_matrix_UB_32 -0.1387384000 _diffrn_orient_matrix_UB_33 -0.0071765000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1519 _reflns_number_total 2019 _reflns_odcompleteness_completeness 99.63 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.232 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.034 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.09(12) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2019 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0419 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0451P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0912 _refine_ls_wR_factor_ref 0.1053 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 -0.04254(4) -0.18109(14) -0.17514(9) 0.0558(3) Uani 1 1 d . . . O1 O -0.13651(14) 0.1711(6) -0.2483(2) 0.0772(9) Uani 1 1 d . . . N1 N 0.05644(13) -0.5347(6) -0.1992(3) 0.0682(9) Uani 1 1 d . . . C1 C -0.07485(15) 0.0632(6) -0.0912(3) 0.0533(8) Uani 1 1 d . . . C2 C -0.04480(16) 0.1056(7) 0.0131(3) 0.0592(10) Uani 1 1 d . . . H2 H -0.0554 0.2307 0.0699 0.071 Uiso 1 1 calc R . . C3 C 0.00376(17) -0.0600(7) 0.0251(3) 0.0625(10) Uani 1 1 d . . . H3 H 0.0285 -0.0560 0.0909 0.075 Uiso 1 1 calc R . . C4 C 0.01099(16) -0.2272(6) -0.0694(3) 0.0538(9) Uani 1 1 d . . . C5 C 0.05584(15) -0.4260(6) -0.0899(3) 0.0525(8) Uani 1 1 d . . . C6 C 0.09456(18) -0.4956(8) -0.0019(4) 0.0740(11) Uani 1 1 d . . . H6 H 0.0933 -0.4153 0.0730 0.089 Uiso 1 1 calc R . . C7 C 0.1353(2) -0.6868(9) -0.0265(5) 0.0838(14) Uani 1 1 d . . . H7 H 0.1619 -0.7387 0.0316 0.101 Uiso 1 1 calc R . . C8 C 0.13604(19) -0.7987(8) -0.1375(6) 0.0872(17) Uani 1 1 d . . . H8 H 0.1633 -0.9268 -0.1570 0.105 Uiso 1 1 calc R . . C9 C 0.09586(19) -0.7185(8) -0.2192(4) 0.0818(13) Uani 1 1 d . . . H9 H 0.0962 -0.7986 -0.2942 0.098 Uiso 1 1 calc R . . C10 C -0.12514(18) 0.1971(7) -0.1416(4) 0.0575(10) Uani 1 1 d . . . C11 C -0.16419(16) 0.3569(6) -0.0648(3) 0.0556(9) Uani 1 1 d . . . C12 C -0.17575(18) 0.2948(7) 0.0541(4) 0.0668(10) Uani 1 1 d . . . H12 H -0.1565 0.1547 0.0903 0.080 Uiso 1 1 calc R . . C13 C -0.21600(18) 0.4410(9) 0.1194(4) 0.0783(12) Uani 1 1 d . . . H13 H -0.2236 0.3981 0.1990 0.094 Uiso 1 1 calc R . . C14 C -0.2442(2) 0.6460(9) 0.0671(5) 0.0797(13) Uani 1 1 d . . . H14 H -0.2714 0.7418 0.1108 0.096 Uiso 1 1 calc R . . C15 C -0.23287(19) 0.7123(8) -0.0493(5) 0.0737(12) Uani 1 1 d . . . H15 H -0.2516 0.8556 -0.0841 0.088 Uiso 1 1 calc R . . C16 C -0.19386(16) 0.5672(6) -0.1146(3) 0.0631(10) Uani 1 1 d . . . H16 H -0.1872 0.6111 -0.1944 0.076 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 0.0617(5) 0.0653(5) 0.0403(5) -0.0025(5) -0.0045(5) -0.0007(4) O1 0.090(2) 0.095(2) 0.0466(17) -0.0013(14) -0.0106(17) 0.0158(16) N1 0.071(2) 0.0742(19) 0.060(2) -0.0126(19) 0.000(2) 0.0052(15) C1 0.0578(19) 0.0573(18) 0.0448(19) 0.0030(19) 0.0022(19) -0.0042(16) C2 0.073(3) 0.063(2) 0.042(2) -0.0065(19) 0.000(2) -0.0024(18) C3 0.069(2) 0.077(2) 0.041(2) -0.003(2) -0.013(2) -0.008(2) C4 0.061(2) 0.0603(19) 0.040(2) 0.0045(19) -0.0026(19) -0.0103(16) C5 0.0518(19) 0.0536(18) 0.052(2) 0.005(2) -0.003(2) -0.0080(15) C6 0.076(3) 0.079(3) 0.067(3) -0.001(2) -0.018(3) -0.001(2) C7 0.070(3) 0.089(3) 0.093(4) 0.010(3) -0.019(3) 0.005(2) C8 0.065(3) 0.079(3) 0.118(5) -0.005(3) 0.005(3) 0.008(2) C9 0.072(3) 0.093(3) 0.080(3) -0.020(3) -0.006(3) 0.013(2) C10 0.066(2) 0.0586(19) 0.048(2) 0.0043(18) 0.005(2) -0.0054(17) C11 0.060(2) 0.0569(19) 0.050(2) -0.0003(19) 0.000(2) -0.0069(16) C12 0.075(3) 0.072(2) 0.054(2) 0.011(2) 0.006(2) 0.000(2) C13 0.076(3) 0.103(3) 0.056(3) -0.002(3) 0.015(2) -0.016(3) C14 0.064(3) 0.092(3) 0.084(3) -0.022(3) 0.012(3) -0.006(2) C15 0.065(3) 0.073(2) 0.083(3) -0.009(2) 0.000(3) 0.005(2) C16 0.067(2) 0.066(2) 0.056(2) 0.004(2) -0.003(2) -0.0016(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.722(3) . ? S1 C4 1.721(4) . ? O1 C10 1.225(4) . ? N1 C5 1.339(5) . ? N1 C9 1.320(4) . ? C1 C2 1.370(5) . ? C1 C10 1.455(5) . ? C2 H2 0.9300 . ? C2 C3 1.404(5) . ? C3 H3 0.9300 . ? C3 C4 1.364(5) . ? C4 C5 1.461(5) . ? C5 C6 1.372(5) . ? C6 H6 0.9300 . ? C6 C7 1.378(6) . ? C7 H7 0.9300 . ? C7 C8 1.362(7) . ? C8 H8 0.9300 . ? C8 C9 1.360(6) . ? C9 H9 0.9300 . ? C10 C11 1.483(5) . ? C11 C12 1.388(5) . ? C11 C16 1.384(5) . ? C12 H12 0.9300 . ? C12 C13 1.393(5) . ? C13 H13 0.9300 . ? C13 C14 1.359(6) . ? C14 H14 0.9300 . ? C14 C15 1.367(6) . ? C15 H15 0.9300 . ? C15 C16 1.371(5) . ? C16 H16 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 C4 S1 C1 91.97(17) . . ? C9 N1 C5 116.9(4) . . ? C2 C1 S1 110.9(3) . . ? C2 C1 C10 131.0(3) . . ? C10 C1 S1 118.0(3) . . ? C1 C2 H2 123.6 . . ? C1 C2 C3 112.8(3) . . ? C3 C2 H2 123.6 . . ? C2 C3 H3 123.3 . . ? C4 C3 C2 113.3(3) . . ? C4 C3 H3 123.3 . . ? C3 C4 S1 111.0(3) . . ? C3 C4 C5 129.6(4) . . ? C5 C4 S1 119.5(3) . . ? N1 C5 C4 115.7(3) . . ? N1 C5 C6 122.6(3) . . ? C6 C5 C4 121.7(3) . . ? C5 C6 H6 120.6 . . ? C5 C6 C7 118.8(4) . . ? C7 C6 H6 120.6 . . ? C6 C7 H7 120.6 . . ? C8 C7 C6 118.9(5) . . ? C8 C7 H7 120.6 . . ? C7 C8 H8 120.8 . . ? C9 C8 C7 118.4(4) . . ? C9 C8 H8 120.8 . . ? N1 C9 C8 124.4(4) . . ? N1 C9 H9 117.8 . . ? C8 C9 H9 117.8 . . ? O1 C10 C1 119.7(4) . . ? O1 C10 C11 119.4(4) . . ? C1 C10 C11 120.9(3) . . ? C12 C11 C10 122.9(3) . . ? C16 C11 C10 119.3(3) . . ? C16 C11 C12 117.7(4) . . ? C11 C12 H12 119.8 . . ? C11 C12 C13 120.4(4) . . ? C13 C12 H12 119.8 . . ? C12 C13 H13 119.9 . . ? C14 C13 C12 120.1(4) . . ? C14 C13 H13 119.9 . . ? C13 C14 H14 119.8 . . ? C13 C14 C15 120.3(4) . . ? C15 C14 H14 119.8 . . ? C14 C15 H15 120.1 . . ? C14 C15 C16 119.9(4) . . ? C16 C15 H15 120.1 . . ? C11 C16 H16 119.2 . . ? C15 C16 C11 121.6(4) . . ? C15 C16 H16 119.2 . . ? data_120810_s2_2244 _database_code_depnum_ccdc_archive 'CCDC 906807' #TrackingRef '14788_web_deposit_cif_file_3_BoLiu_1350627676.4f.cif' _audit_creation_date 2012-08-10 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H5 F N2 S' _chemical_formula_sum 'C10 H5 F N2 S' _chemical_formula_weight 204.22 _chemical_melting_point ? _chemical_oxdiff_formula C12H10N4O3S1F1 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.7553(3) _cell_length_b 9.2885(5) _cell_length_c 14.5501(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.168(4) _cell_angle_gamma 90.00 _cell_volume 909.26(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1489 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.1801 _cell_measurement_theta_min 3.0217 _exptl_absorpt_coefficient_mu 0.326 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.99392 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 416 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_unetI/netI 0.0387 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 4062 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.22 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -25.00 23.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -16.7361 -99.0000 -90.0000 48 #__ type_ start__ end____ width___ exp.time_ 2 omega -91.00 -47.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -16.7361 -178.0000 120.0000 44 #__ type_ start__ end____ width___ exp.time_ 3 omega -34.00 84.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.8611 0.0000 -150.0000 118 #__ type_ start__ end____ width___ exp.time_ 4 omega -43.00 -18.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -16.7361 37.0000 90.0000 25 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0526070000 _diffrn_orient_matrix_UB_12 -0.0096567000 _diffrn_orient_matrix_UB_13 0.0440291000 _diffrn_orient_matrix_UB_21 -0.0305963000 _diffrn_orient_matrix_UB_22 -0.0730273000 _diffrn_orient_matrix_UB_23 0.0001279000 _diffrn_orient_matrix_UB_31 0.0860358000 _diffrn_orient_matrix_UB_32 -0.0200698000 _diffrn_orient_matrix_UB_33 -0.0214559000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1432 _reflns_number_total 1868 _reflns_odcompleteness_completeness 99.80 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.201 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1868 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0394 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0901 _refine_ls_wR_factor_ref 0.1007 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.52525(7) 0.28949(6) 0.50556(3) 0.0451(2) Uani 1 1 d . . . F1 F 0.87262(17) 0.12076(14) 0.77035(8) 0.0612(4) Uani 1 1 d . . . N1 N 0.8999(2) 0.38526(19) 0.59164(10) 0.0448(4) Uani 1 1 d . . . N2 N 0.0422(3) 0.1668(3) 0.38124(15) 0.0817(7) Uani 1 1 d . . . C1 C 1.0773(3) 0.4408(2) 0.61854(14) 0.0489(5) Uani 1 1 d . . . H1 H 1.1243 0.5157 0.5841 0.059 Uiso 1 1 calc R . . C2 C 1.1953(3) 0.3931(2) 0.69484(14) 0.0462(5) Uani 1 1 d . . . H2 H 1.3193 0.4340 0.7107 0.055 Uiso 1 1 calc R . . C3 C 1.1259(3) 0.2847(2) 0.74661(13) 0.0453(5) Uani 1 1 d . . . H3 H 1.2007 0.2501 0.7987 0.054 Uiso 1 1 calc R . . C4 C 0.9429(3) 0.2286(2) 0.71938(13) 0.0392(5) Uani 1 1 d . . . C5 C 0.8306(2) 0.2774(2) 0.64140(12) 0.0354(4) Uani 1 1 d . . . C6 C 0.6378(3) 0.2175(2) 0.60620(12) 0.0359(4) Uani 1 1 d . . . C7 C 0.5270(3) 0.1094(2) 0.63849(13) 0.0444(5) Uani 1 1 d . . . H7 H 0.5642 0.0584 0.6923 0.053 Uiso 1 1 calc R . . C8 C 0.3515(3) 0.0828(2) 0.58262(14) 0.0472(5) Uani 1 1 d . . . H8 H 0.2596 0.0125 0.5951 0.057 Uiso 1 1 calc R . . C9 C 0.3306(3) 0.1714(2) 0.50810(14) 0.0435(5) Uani 1 1 d . . . C10 C 0.1704(3) 0.1705(3) 0.43755(15) 0.0541(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0387(3) 0.0509(4) 0.0437(3) 0.0060(2) -0.0082(2) -0.0074(2) F1 0.0594(8) 0.0648(9) 0.0564(7) 0.0224(7) -0.0113(6) -0.0086(6) N1 0.0408(9) 0.0508(11) 0.0415(9) 0.0047(8) -0.0029(7) -0.0087(8) N2 0.0544(12) 0.0941(19) 0.0900(16) 0.0008(13) -0.0307(11) -0.0085(12) C1 0.0431(11) 0.0526(14) 0.0507(12) 0.0009(11) 0.0028(9) -0.0127(10) C2 0.0356(10) 0.0506(13) 0.0509(12) -0.0146(11) -0.0036(9) -0.0052(9) C3 0.0409(11) 0.0510(14) 0.0416(11) -0.0072(10) -0.0091(9) 0.0058(9) C4 0.0395(10) 0.0406(12) 0.0369(10) 0.0004(9) -0.0006(8) 0.0025(9) C5 0.0320(9) 0.0397(11) 0.0338(10) -0.0029(9) -0.0005(8) -0.0003(8) C6 0.0319(9) 0.0427(12) 0.0324(10) -0.0006(8) -0.0015(7) 0.0022(8) C7 0.0401(11) 0.0475(13) 0.0448(11) 0.0055(10) -0.0004(9) -0.0052(9) C8 0.0376(10) 0.0483(13) 0.0557(13) -0.0037(11) 0.0034(9) -0.0096(9) C9 0.0322(10) 0.0496(13) 0.0477(11) -0.0094(10) -0.0023(9) -0.0018(9) C10 0.0389(11) 0.0595(14) 0.0616(14) -0.0046(12) -0.0077(10) -0.0069(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C6 1.7230(18) . ? S1 C9 1.715(2) . ? F1 C4 1.357(2) . ? N1 C1 1.331(2) . ? N1 C5 1.345(2) . ? N2 C10 1.138(3) . ? C1 H1 0.9300 . ? C1 C2 1.380(3) . ? C2 H2 0.9300 . ? C2 C3 1.366(3) . ? C3 H3 0.9300 . ? C3 C4 1.366(3) . ? C4 C5 1.384(3) . ? C5 C6 1.465(2) . ? C6 C7 1.361(3) . ? C7 H7 0.9300 . ? C7 C8 1.398(3) . ? C8 H8 0.9300 . ? C8 C9 1.358(3) . ? C9 C10 1.423(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 S1 C6 90.80(9) . . ? C1 N1 C5 118.60(17) . . ? N1 C1 H1 118.3 . . ? N1 C1 C2 123.5(2) . . ? C2 C1 H1 118.3 . . ? C1 C2 H2 120.7 . . ? C3 C2 C1 118.58(18) . . ? C3 C2 H2 120.7 . . ? C2 C3 H3 121.1 . . ? C2 C3 C4 117.89(19) . . ? C4 C3 H3 121.1 . . ? F1 C4 C3 118.36(18) . . ? F1 C4 C5 119.79(17) . . ? C3 C4 C5 121.85(19) . . ? N1 C5 C4 119.59(17) . . ? N1 C5 C6 115.87(16) . . ? C4 C5 C6 124.53(18) . . ? C5 C6 S1 117.38(14) . . ? C7 C6 S1 111.44(14) . . ? C7 C6 C5 131.18(17) . . ? C6 C7 H7 123.4 . . ? C6 C7 C8 113.17(18) . . ? C8 C7 H7 123.4 . . ? C7 C8 H8 123.9 . . ? C9 C8 C7 112.28(18) . . ? C9 C8 H8 123.9 . . ? C8 C9 S1 112.31(15) . . ? C8 C9 C10 126.17(19) . . ? C10 C9 S1 121.52(16) . . ? N2 C10 C9 178.6(3) . . ? data_1 _database_code_depnum_ccdc_archive 'CCDC 906808' #TrackingRef '14789_web_deposit_cif_file_4_BoLiu_1350627676.4c.cif' _audit_creation_date 2012-09-04 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H12 N O2 S' _chemical_formula_sum 'C16 H12 N O2 S' _chemical_formula_weight 282.33 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula C12H10N4O3S1 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' _space_group_crystal_system triclinic _space_group_IT_number 1 _space_group_name_H-M_alt 'P 1' _space_group_name_Hall 'P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' _cell_length_a 6.0479(4) _cell_length_b 8.1021(5) _cell_length_c 14.5564(10) _cell_angle_alpha 81.543(6) _cell_angle_beta 83.748(5) _cell_angle_gamma 72.375(6) _cell_volume 670.83(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1465 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.8920 _cell_measurement_theta_min 3.1530 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.98593 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 294 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_unetI/netI 0.0446 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 5668 _diffrn_reflns_theta_full 26.36 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_min 3.16 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -24.00 19.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -99.0000 -90.0000 43 #__ type_ start__ end____ width___ exp.time_ 2 omega -90.00 -35.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -178.0000 -120.0000 55 #__ type_ start__ end____ width___ exp.time_ 3 omega -25.00 21.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -99.0000 30.0000 46 #__ type_ start__ end____ width___ exp.time_ 4 omega -92.00 -53.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -178.0000 150.0000 39 #__ type_ start__ end____ width___ exp.time_ 5 omega -5.00 90.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 20.0174 37.0000 -150.0000 95 #__ type_ start__ end____ width___ exp.time_ 6 omega -31.00 64.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 20.0174 -19.0000 0.0000 95 #__ type_ start__ end____ width___ exp.time_ 7 omega -52.00 10.00 1.0000 6.0000 omega____ theta____ kappa____ phi______ frames - 20.0174 -37.0000 150.0000 62 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0174768000 _diffrn_orient_matrix_UB_12 -0.0282825000 _diffrn_orient_matrix_UB_13 -0.0417749000 _diffrn_orient_matrix_UB_21 -0.1165453000 _diffrn_orient_matrix_UB_22 0.0544417000 _diffrn_orient_matrix_UB_23 0.0016238000 _diffrn_orient_matrix_UB_31 0.0364081000 _diffrn_orient_matrix_UB_32 0.0692686000 _diffrn_orient_matrix_UB_33 -0.0262769000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3238 _reflns_number_total 4305 _reflns_odcompleteness_completeness 99.78 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.626 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.089 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.22(13) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 363 _refine_ls_number_reflns 4305 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1016 _refine_ls_R_factor_gt 0.0796 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1494P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2035 _refine_ls_wR_factor_ref 0.2322 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 1.0028(3) 0.1471(2) 0.27745(13) 0.0624(6) Uani 1 1 d . . . S2 S 0.9533(3) 0.5080(2) 0.04170(12) 0.0613(6) Uani 1 1 d . . . O1 O 1.3544(10) -0.2465(8) -0.1733(4) 0.0861(16) Uani 1 1 d . . . O2 O 0.9650(8) -0.1240(6) -0.1504(3) 0.0624(12) Uani 1 1 d . . . O3 O 1.0786(10) 0.7461(7) 0.4740(4) 0.0752(15) Uani 1 1 d . . . O4 O 1.4627(9) 0.6202(6) 0.4660(3) 0.0787(15) Uani 1 1 d . . . N2 N 1.0321(9) 0.0227(7) 0.0992(3) 0.0480(13) Uani 1 1 d . . . N4 N 1.0414(9) 0.5924(7) 0.2160(3) 0.0484(13) Uani 1 1 d . . . C1 C 1.2567(10) 0.0341(7) 0.2241(4) 0.0388(13) Uani 1 1 d . . . C2 C 1.4777(9) -0.0070(6) 0.2704(3) 0.0312(11) Uani 1 1 d . . . C3 C 1.3863(10) 0.0794(7) 0.3606(4) 0.0447(14) Uani 1 1 d . . . C4 C 1.1508(10) 0.1623(7) 0.3708(4) 0.0422(13) Uani 1 1 d . . . C5 C 1.0514(13) 0.2482(9) 0.4464(4) 0.0544(17) Uani 1 1 d . . . H5 H 0.8926 0.3044 0.4514 0.065 Uiso 1 1 calc R . . C6 C 1.1910(13) 0.2496(10) 0.5145(4) 0.0650(19) Uani 1 1 d . . . H6 H 1.1267 0.3090 0.5656 0.078 Uiso 1 1 calc R . . C7 C 1.4235(13) 0.1644(10) 0.5077(4) 0.0621(18) Uani 1 1 d . . . H7 H 1.5141 0.1650 0.5553 0.075 Uiso 1 1 calc R . . C8 C 1.5275(12) 0.0779(9) 0.4328(4) 0.0597(17) Uani 1 1 d . . . H8 H 1.6860 0.0200 0.4294 0.072 Uiso 1 1 calc R . . C9 C 1.2438(10) -0.0219(7) 0.1325(4) 0.0411(13) Uani 1 1 d . . . C10 C 1.4429(10) -0.1119(7) 0.0836(4) 0.0492(14) Uani 1 1 d . . . H10 H 1.5873 -0.1396 0.1080 0.059 Uiso 1 1 calc R . . C11 C 1.4247(10) -0.1593(8) -0.0004(4) 0.0532(16) Uani 1 1 d . . . H11 H 1.5568 -0.2198 -0.0339 0.064 Uiso 1 1 calc R . . C12 C 1.2074(10) -0.1167(7) -0.0361(4) 0.0413(13) Uani 1 1 d . . . C13 C 1.0129(11) -0.0273(8) 0.0176(4) 0.0467(15) Uani 1 1 d . . . H13 H 0.8660 -0.0019 -0.0043 0.056 Uiso 1 1 calc R . . C14 C 1.1842(12) -0.1713(8) -0.1267(4) 0.0515(15) Uani 1 1 d . . . C15 C 0.9194(15) -0.1762(10) -0.2367(5) 0.077(2) Uani 1 1 d . . . H15A H 0.7662 -0.1932 -0.2308 0.092 Uiso 1 1 calc R . . H15B H 1.0332 -0.2856 -0.2489 0.092 Uiso 1 1 calc R . . C16 C 0.9321(16) -0.0406(10) -0.3141(5) 0.092(3) Uani 1 1 d . . . H16A H 0.8945 -0.0724 -0.3702 0.137 Uiso 1 1 calc R . . H16B H 1.0867 -0.0291 -0.3222 0.137 Uiso 1 1 calc R . . H16C H 0.8236 0.0685 -0.3007 0.137 Uiso 1 1 calc R . . C17 C 1.2245(9) 0.4482(7) 0.0848(4) 0.0405(13) Uani 1 1 d . . . C18 C 1.4218(9) 0.3501(5) 0.0267(3) 0.0299(11) Uani 1 1 d . . . C19 C 1.3033(10) 0.3312(7) -0.0573(4) 0.0438(13) Uani 1 1 d . . . C20 C 1.0612(10) 0.4099(7) -0.0561(4) 0.0445(14) Uani 1 1 d . . . C21 C 0.9358(12) 0.4022(8) -0.1290(4) 0.0544(17) Uani 1 1 d . . . H21 H 0.7761 0.4554 -0.1276 0.065 Uiso 1 1 calc R . . C22 C 1.0461(15) 0.3171(10) -0.2023(5) 0.072(2) Uani 1 1 d . . . H22 H 0.9613 0.3101 -0.2504 0.087 Uiso 1 1 calc R . . C23 C 1.2889(13) 0.2392(9) -0.2056(4) 0.0602(17) Uani 1 1 d . . . H23 H 1.3641 0.1835 -0.2567 0.072 Uiso 1 1 calc R . . C24 C 1.4134(10) 0.2449(8) -0.1347(4) 0.0536(15) Uani 1 1 d . . . H24 H 1.5731 0.1914 -0.1371 0.064 Uiso 1 1 calc R . . C25 C 1.2440(10) 0.5000(8) 0.1745(4) 0.0390(13) Uani 1 1 d . . . C26 C 1.4559(10) 0.4628(8) 0.2106(4) 0.0462(14) Uani 1 1 d . . . H26 H 1.5915 0.4038 0.1785 0.055 Uiso 1 1 calc R . . C27 C 1.4623(11) 0.5151(8) 0.2957(4) 0.0504(15) Uani 1 1 d . . . H27 H 1.6038 0.4873 0.3225 0.060 Uiso 1 1 calc R . . C28 C 1.2673(10) 0.6059(8) 0.3410(4) 0.0434(13) Uani 1 1 d . . . C29 C 1.0600(11) 0.6410(8) 0.3002(4) 0.0518(16) Uani 1 1 d . . . H29 H 0.9246 0.7014 0.3319 0.062 Uiso 1 1 calc R . . C30 C 1.2529(12) 0.6655(8) 0.4337(4) 0.0531(16) Uani 1 1 d . . . C31 C 1.470(3) 0.6698(12) 0.5580(6) 0.147(6) Uani 1 1 d . . . H31A H 1.5433 0.7626 0.5503 0.176 Uiso 1 1 calc R . . H31B H 1.3113 0.7174 0.5827 0.176 Uiso 1 1 calc R . . C32 C 1.574(3) 0.5517(14) 0.6177(7) 0.202(8) Uani 1 1 d . . . H32A H 1.5709 0.4405 0.6034 0.303 Uiso 1 1 calc R . . H32B H 1.4984 0.5713 0.6783 0.303 Uiso 1 1 calc R . . H32C H 1.7324 0.5529 0.6170 0.303 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 0.0502(10) 0.0735(12) 0.0584(11) -0.0175(9) -0.0027(8) -0.0065(8) S2 0.0498(10) 0.0744(12) 0.0582(11) -0.0111(9) -0.0096(8) -0.0124(9) O1 0.071(3) 0.109(4) 0.081(3) -0.057(3) 0.008(3) -0.013(3) O2 0.062(3) 0.067(3) 0.056(3) -0.017(2) -0.015(2) -0.008(2) O3 0.085(4) 0.074(3) 0.065(3) -0.030(3) 0.007(3) -0.014(3) O4 0.097(4) 0.078(3) 0.058(3) -0.028(3) -0.032(3) -0.002(3) N2 0.034(3) 0.058(3) 0.050(3) -0.012(2) -0.002(2) -0.008(2) N4 0.043(3) 0.057(3) 0.045(3) -0.011(2) -0.008(2) -0.011(2) C1 0.038(3) 0.039(3) 0.037(3) -0.003(2) -0.001(2) -0.009(2) C2 0.049(3) 0.030(2) 0.019(2) 0.0057(19) -0.012(2) -0.019(2) C3 0.042(3) 0.047(3) 0.044(3) 0.001(3) -0.006(3) -0.013(3) C4 0.037(3) 0.052(3) 0.038(3) -0.004(3) -0.008(2) -0.011(3) C5 0.055(4) 0.071(4) 0.039(3) -0.012(3) 0.003(3) -0.021(4) C6 0.074(5) 0.087(5) 0.040(3) -0.013(3) 0.003(3) -0.033(4) C7 0.076(5) 0.086(5) 0.033(3) -0.004(3) -0.015(3) -0.033(4) C8 0.046(4) 0.071(4) 0.054(4) 0.011(3) -0.010(3) -0.011(3) C9 0.040(3) 0.040(3) 0.040(3) -0.003(2) -0.001(2) -0.009(3) C10 0.039(3) 0.052(4) 0.055(4) -0.008(3) -0.002(3) -0.011(3) C11 0.040(3) 0.059(4) 0.054(4) -0.006(3) -0.002(3) -0.005(3) C12 0.040(3) 0.041(3) 0.042(3) -0.005(2) -0.008(2) -0.008(2) C13 0.038(3) 0.052(4) 0.048(3) -0.007(3) -0.006(3) -0.008(3) C14 0.058(4) 0.049(4) 0.045(3) -0.008(3) -0.004(3) -0.012(3) C15 0.089(6) 0.083(5) 0.068(4) -0.024(4) -0.006(4) -0.033(5) C16 0.125(8) 0.095(6) 0.060(5) -0.026(4) -0.007(5) -0.031(6) C17 0.031(3) 0.045(3) 0.046(3) 0.000(3) -0.008(2) -0.012(2) C18 0.052(3) 0.024(2) 0.015(2) -0.0034(17) 0.0057(19) -0.015(2) C19 0.046(3) 0.042(3) 0.042(3) -0.001(3) -0.001(2) -0.015(3) C20 0.044(3) 0.048(4) 0.041(3) 0.002(3) -0.006(2) -0.015(3) C21 0.050(4) 0.063(4) 0.051(4) -0.008(3) -0.013(3) -0.013(3) C22 0.094(6) 0.072(5) 0.062(4) -0.003(4) -0.021(4) -0.037(5) C23 0.070(5) 0.068(4) 0.046(3) -0.014(3) -0.005(3) -0.021(4) C24 0.039(3) 0.060(4) 0.057(4) -0.015(3) 0.003(3) -0.007(3) C25 0.043(3) 0.040(3) 0.034(3) -0.001(2) -0.002(2) -0.013(2) C26 0.031(3) 0.060(4) 0.043(3) -0.006(3) -0.003(2) -0.008(3) C27 0.050(4) 0.061(4) 0.041(3) -0.004(3) -0.009(3) -0.017(3) C28 0.046(3) 0.044(3) 0.041(3) -0.007(2) 0.000(2) -0.014(3) C29 0.047(4) 0.050(4) 0.052(4) -0.014(3) 0.004(3) -0.005(3) C30 0.059(4) 0.050(4) 0.049(3) -0.009(3) -0.005(3) -0.013(3) C31 0.278(17) 0.086(6) 0.071(5) -0.035(5) -0.080(8) -0.008(8) C32 0.36(2) 0.111(8) 0.068(5) -0.044(5) -0.106(9) 0.086(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.702(5) . ? S1 C4 1.745(6) . ? S2 C17 1.724(6) . ? S2 C20 1.703(6) . ? O1 C14 1.217(8) . ? O2 C14 1.333(8) . ? O2 C15 1.461(8) . ? O3 C30 1.201(8) . ? O4 C30 1.328(8) . ? O4 C31 1.463(8) . ? N2 C9 1.345(8) . ? N2 C13 1.338(8) . ? N4 C25 1.357(8) . ? N4 C29 1.367(8) . ? C1 C2 1.487(8) . ? C1 C9 1.488(8) . ? C2 C3 1.548(8) . ? C3 C4 1.380(8) . ? C3 C8 1.422(8) . ? C4 C5 1.372(8) . ? C5 H5 0.9300 . ? C5 C6 1.374(10) . ? C6 H6 0.9300 . ? C6 C7 1.366(10) . ? C7 H7 0.9300 . ? C7 C8 1.373(10) . ? C8 H8 0.9300 . ? C9 C10 1.387(8) . ? C10 H10 0.9300 . ? C10 C11 1.359(9) . ? C11 H11 0.9300 . ? C11 C12 1.392(8) . ? C12 C13 1.404(7) . ? C12 C14 1.484(8) . ? C13 H13 0.9300 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C16 1.466(10) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.475(7) . ? C17 C25 1.456(8) . ? C18 C19 1.531(7) . ? C19 C20 1.408(8) . ? C19 C24 1.410(8) . ? C20 C21 1.389(8) . ? C21 H21 0.9300 . ? C21 C22 1.357(10) . ? C22 H22 0.9300 . ? C22 C23 1.411(11) . ? C23 H23 0.9300 . ? C23 C24 1.357(9) . ? C24 H24 0.9300 . ? C25 C26 1.370(8) . ? C26 H26 0.9300 . ? C26 C27 1.375(8) . ? C27 H27 0.9300 . ? C27 C28 1.347(8) . ? C28 C29 1.379(9) . ? C28 C30 1.484(8) . ? C29 H29 0.9300 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 C32 1.255(12) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 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 C1 S1 C4 90.6(3) . . ? C20 S2 C17 92.1(3) . . ? C14 O2 C15 118.1(5) . . ? C30 O4 C31 115.3(7) . . ? C13 N2 C9 118.6(5) . . ? C25 N4 C29 115.2(5) . . ? C2 C1 S1 119.8(4) . . ? C2 C1 C9 123.1(5) . . ? C9 C1 S1 117.2(4) . . ? C1 C2 C3 100.2(4) . . ? C4 C3 C2 117.1(5) . . ? C4 C3 C8 118.4(6) . . ? C8 C3 C2 124.5(5) . . ? C3 C4 S1 112.4(4) . . ? C5 C4 S1 125.4(5) . . ? C5 C4 C3 122.2(6) . . ? C4 C5 H5 120.6 . . ? C4 C5 C6 118.7(7) . . ? C6 C5 H5 120.6 . . ? C5 C6 H6 119.8 . . ? C7 C6 C5 120.5(7) . . ? C7 C6 H6 119.8 . . ? C6 C7 H7 119.0 . . ? C6 C7 C8 122.0(6) . . ? C8 C7 H7 119.0 . . ? C3 C8 H8 120.9 . . ? C7 C8 C3 118.1(6) . . ? C7 C8 H8 120.9 . . ? N2 C9 C1 116.8(5) . . ? N2 C9 C10 122.3(5) . . ? C10 C9 C1 120.9(5) . . ? C9 C10 H10 120.4 . . ? C11 C10 C9 119.2(6) . . ? C11 C10 H10 120.4 . . ? C10 C11 H11 120.1 . . ? C10 C11 C12 119.7(6) . . ? C12 C11 H11 120.1 . . ? C11 C12 C13 118.0(6) . . ? C11 C12 C14 120.3(6) . . ? C13 C12 C14 121.7(6) . . ? N2 C13 C12 122.1(6) . . ? N2 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? O1 C14 O2 125.7(6) . . ? O1 C14 C12 121.1(6) . . ? O2 C14 C12 113.1(5) . . ? O2 C15 H15A 109.8 . . ? O2 C15 H15B 109.8 . . ? O2 C15 C16 109.6(6) . . ? H15A C15 H15B 108.2 . . ? C16 C15 H15A 109.8 . . ? C16 C15 H15B 109.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 S2 117.1(4) . . ? C25 C17 S2 118.2(4) . . ? C25 C17 C18 124.6(5) . . ? C17 C18 C19 102.4(4) . . ? C20 C19 C18 115.8(5) . . ? C20 C19 C24 117.9(5) . . ? C24 C19 C18 126.3(5) . . ? C19 C20 S2 112.4(4) . . ? C21 C20 S2 126.7(5) . . ? C21 C20 C19 120.8(6) . . ? C20 C21 H21 120.0 . . ? C22 C21 C20 120.0(7) . . ? C22 C21 H21 120.0 . . ? C21 C22 H22 119.9 . . ? C21 C22 C23 120.2(7) . . ? C23 C22 H22 119.9 . . ? C22 C23 H23 119.8 . . ? C24 C23 C22 120.4(6) . . ? C24 C23 H23 119.8 . . ? C19 C24 H24 119.7 . . ? C23 C24 C19 120.7(6) . . ? C23 C24 H24 119.7 . . ? N4 C25 C17 115.3(5) . . ? N4 C25 C26 123.7(5) . . ? C26 C25 C17 121.0(5) . . ? C25 C26 H26 121.0 . . ? C25 C26 C27 118.1(5) . . ? C27 C26 H26 121.0 . . ? C26 C27 H27 119.4 . . ? C28 C27 C26 121.1(6) . . ? C28 C27 H27 119.4 . . ? C27 C28 C29 117.8(6) . . ? C27 C28 C30 125.7(6) . . ? C29 C28 C30 116.4(6) . . ? N4 C29 C28 124.0(6) . . ? N4 C29 H29 118.0 . . ? C28 C29 H29 118.0 . . ? O3 C30 O4 124.0(6) . . ? O3 C30 C28 125.6(7) . . ? O4 C30 C28 110.3(6) . . ? O4 C31 H31A 108.1 . . ? O4 C31 H31B 108.1 . . ? H31A C31 H31B 107.3 . . ? C32 C31 O4 116.9(8) . . ? C32 C31 H31A 108.1 . . ? C32 C31 H31B 108.1 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32B 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ?