# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email kms@iisertvm.ac.in _publ_contact_author_name 'Kana Sureshan' loop_ _publ_author_name K.Sureshan S.Kota A.Vidyasagar R.Gonnade A.Naidu data_kms4 _database_code_depnum_ccdc_archive 'CCDC 795697' #TrackingRef '- kms4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H11 N O S' _chemical_formula_sum 'C16 H11 N O S' _chemical_formula_weight 265.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.359(3) _cell_length_b 11.451(3) _cell_length_c 9.571(2) _cell_angle_alpha 90.00 _cell_angle_beta 117.517(4) _cell_angle_gamma 90.00 _cell_volume 1298.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1481 _cell_measurement_theta_min 2.474 _cell_measurement_theta_max 25.452 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9436 _exptl_absorpt_correction_T_max 0.9835 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3233 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1676 _reflns_number_gt 1600 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.1057P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(9) _refine_ls_number_reflns 1676 _refine_ls_number_parameters 176 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.133 _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 0.73064(8) 0.79212(6) 0.76078(9) 0.0575(2) Uani 1 1 d . . . O1 O 0.8361(2) 0.9401(2) 1.0265(2) 0.0690(7) Uani 1 1 d . . . N1 N 0.59681(19) 0.93750(19) 0.5325(3) 0.0460(6) Uani 1 1 d . . . C2 C 0.6715(2) 0.9303(2) 0.6807(3) 0.0437(7) Uani 1 1 d . . . C3 C 0.7101(2) 1.0308(2) 0.7834(3) 0.0449(7) Uani 1 1 d . . . C4 C 0.6655(2) 1.1366(2) 0.7209(3) 0.0494(7) Uani 1 1 d . . . H4 H 0.6890 1.2027 0.7844 0.059 Uiso 1 1 calc R . . C5 C 0.5357(3) 1.2559(3) 0.4889(4) 0.0600(8) Uani 1 1 d . . . H5 H 0.5568 1.3245 0.5474 0.072 Uiso 1 1 calc R . . C6 C 0.4587(3) 1.2598(3) 0.3343(4) 0.0617(8) Uani 1 1 d . . . H6 H 0.4272 1.3307 0.2874 0.074 Uiso 1 1 calc R . . C7 C 0.4269(3) 1.1575(3) 0.2465(4) 0.0606(8) Uani 1 1 d . . . H7 H 0.3736 1.1609 0.1409 0.073 Uiso 1 1 calc R . . C8 C 0.4721(3) 1.0524(3) 0.3114(3) 0.0557(8) Uani 1 1 d . . . H8 H 0.4499 0.9853 0.2496 0.067 Uiso 1 1 calc R . . C9 C 0.5523(2) 1.0444(2) 0.4717(3) 0.0429(6) Uani 1 1 d . . . C10 C 0.5846(2) 1.1479(2) 0.5623(3) 0.0465(7) Uani 1 1 d . . . C11 C 0.7935(3) 1.0264(3) 0.9515(3) 0.0531(7) Uani 1 1 d . . . C12 C 0.6804(3) 0.7008(2) 0.5904(3) 0.0502(7) Uani 1 1 d . . . C13 C 0.7606(3) 0.6507(3) 0.5560(4) 0.0658(9) Uani 1 1 d . . . H13 H 0.8362 0.6712 0.6138 0.079 Uiso 1 1 calc R . . C14 C 0.7279(4) 0.5700(3) 0.4352(5) 0.0785(11) Uani 1 1 d . . . H14 H 0.7820 0.5352 0.4131 0.094 Uiso 1 1 calc R . . C15 C 0.6164(4) 0.5411(3) 0.3480(4) 0.0711(10) Uani 1 1 d . . . H15 H 0.5948 0.4869 0.2668 0.085 Uiso 1 1 calc R . . C16 C 0.5371(3) 0.5919(3) 0.3804(4) 0.0641(9) Uani 1 1 d . . . H16 H 0.4614 0.5731 0.3196 0.077 Uiso 1 1 calc R . . C17 C 0.5680(3) 0.6714(2) 0.5028(3) 0.0535(7) Uani 1 1 d . . . H17 H 0.5137 0.7044 0.5258 0.064 Uiso 1 1 calc R . . H11 H 0.817(3) 1.105(3) 1.004(4) 0.069(10) Uiso 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 0.0618(5) 0.0462(3) 0.0465(4) 0.0093(3) 0.0098(3) 0.0029(4) O1 0.0694(16) 0.0797(15) 0.0417(12) 0.0103(11) 0.0118(11) 0.0164(12) N1 0.0449(14) 0.0446(12) 0.0414(13) 0.0043(10) 0.0139(11) -0.0005(10) C2 0.0422(16) 0.0442(14) 0.0418(16) 0.0051(10) 0.0171(13) 0.0005(11) C3 0.0447(17) 0.0489(14) 0.0395(15) 0.0024(12) 0.0180(12) -0.0014(12) C4 0.0562(18) 0.0485(15) 0.0407(15) -0.0055(12) 0.0201(13) -0.0043(13) C5 0.072(2) 0.0498(16) 0.0557(18) 0.0036(14) 0.0274(16) 0.0093(15) C6 0.068(2) 0.0544(17) 0.061(2) 0.0143(14) 0.0285(17) 0.0191(15) C7 0.0527(18) 0.0710(19) 0.0467(17) 0.0122(15) 0.0134(14) 0.0128(15) C8 0.054(2) 0.0566(17) 0.0452(17) -0.0012(13) 0.0136(14) 0.0026(13) C9 0.0387(16) 0.0455(14) 0.0408(15) 0.0038(11) 0.0152(12) 0.0015(11) C10 0.0525(17) 0.0441(14) 0.0417(14) 0.0013(11) 0.0208(13) 0.0004(12) C11 0.0523(19) 0.0637(18) 0.0385(16) -0.0028(14) 0.0170(13) -0.0025(15) C12 0.0616(19) 0.0335(13) 0.0519(17) 0.0139(11) 0.0232(15) 0.0063(12) C13 0.058(2) 0.0494(16) 0.086(2) 0.0131(16) 0.0293(18) 0.0152(15) C14 0.097(3) 0.0557(19) 0.100(3) 0.0093(19) 0.060(3) 0.0241(19) C15 0.108(3) 0.0462(16) 0.063(2) -0.0003(14) 0.042(2) 0.0046(18) C16 0.076(2) 0.0470(16) 0.063(2) -0.0011(14) 0.0260(17) -0.0050(16) C17 0.0532(18) 0.0504(15) 0.0541(17) 0.0001(13) 0.0224(14) -0.0007(13) _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 C2 1.777(3) . ? S1 C12 1.787(3) . ? O1 C11 1.200(3) . ? N1 C2 1.306(3) . ? N1 C9 1.368(3) . ? C2 C3 1.445(4) . ? C3 C4 1.361(4) . ? C3 C11 1.475(4) . ? C4 C10 1.405(4) . ? C4 H4 0.9300 . ? C5 C6 1.357(4) . ? C5 C10 1.424(4) . ? C5 H5 0.9300 . ? C6 C7 1.389(4) . ? C6 H6 0.9300 . ? C7 C8 1.360(4) . ? C7 H7 0.9300 . ? C8 C9 1.411(4) . ? C8 H8 0.9300 . ? C9 C10 1.412(4) . ? C11 H11 1.01(3) . ? C12 C17 1.382(4) . ? C12 C13 1.382(4) . ? C13 C14 1.384(5) . ? C13 H13 0.9300 . ? C14 C15 1.370(6) . ? C14 H14 0.9300 . ? C15 C16 1.364(5) . ? C15 H15 0.9300 . ? C16 C17 1.387(4) . ? C16 H16 0.9300 . ? C17 H17 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 C2 S1 C12 102.89(12) . . ? C2 N1 C9 118.8(2) . . ? N1 C2 C3 122.8(2) . . ? N1 C2 S1 119.3(2) . . ? C3 C2 S1 117.90(19) . . ? C4 C3 C2 117.6(2) . . ? C4 C3 C11 117.8(2) . . ? C2 C3 C11 124.6(2) . . ? C3 C4 C10 121.2(3) . . ? C3 C4 H4 119.4 . . ? C10 C4 H4 119.4 . . ? C6 C5 C10 120.7(3) . . ? C6 C5 H5 119.7 . . ? C10 C5 H5 119.7 . . ? C5 C6 C7 119.9(3) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 121.5(3) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 120.5(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? N1 C9 C8 118.9(2) . . ? N1 C9 C10 122.6(2) . . ? C8 C9 C10 118.5(2) . . ? C4 C10 C9 116.8(2) . . ? C4 C10 C5 124.1(3) . . ? C9 C10 C5 119.0(3) . . ? O1 C11 C3 126.2(3) . . ? O1 C11 H11 119.1(17) . . ? C3 C11 H11 114.7(17) . . ? C17 C12 C13 120.0(3) . . ? C17 C12 S1 122.7(2) . . ? C13 C12 S1 117.1(3) . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 119.9(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 120.9(3) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 119.2(3) . . ? C12 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? 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 C9 N1 C2 C3 -0.5(4) . . . . ? C9 N1 C2 S1 -179.59(19) . . . . ? C12 S1 C2 N1 9.2(3) . . . . ? C12 S1 C2 C3 -169.9(2) . . . . ? N1 C2 C3 C4 0.1(4) . . . . ? S1 C2 C3 C4 179.2(2) . . . . ? N1 C2 C3 C11 179.5(3) . . . . ? S1 C2 C3 C11 -1.5(4) . . . . ? C2 C3 C4 C10 0.1(4) . . . . ? C11 C3 C4 C10 -179.2(3) . . . . ? C10 C5 C6 C7 0.0(5) . . . . ? C5 C6 C7 C8 -0.5(5) . . . . ? C6 C7 C8 C9 0.6(5) . . . . ? C2 N1 C9 C8 179.6(3) . . . . ? C2 N1 C9 C10 0.6(4) . . . . ? C7 C8 C9 N1 -179.3(3) . . . . ? C7 C8 C9 C10 -0.2(5) . . . . ? C3 C4 C10 C9 0.0(4) . . . . ? C3 C4 C10 C5 -179.1(3) . . . . ? N1 C9 C10 C4 -0.3(4) . . . . ? C8 C9 C10 C4 -179.4(3) . . . . ? N1 C9 C10 C5 178.8(3) . . . . ? C8 C9 C10 C5 -0.2(4) . . . . ? C6 C5 C10 C4 179.4(3) . . . . ? C6 C5 C10 C9 0.4(5) . . . . ? C4 C3 C11 O1 175.7(3) . . . . ? C2 C3 C11 O1 -3.6(5) . . . . ? C2 S1 C12 C17 -68.0(2) . . . . ? C2 S1 C12 C13 117.8(2) . . . . ? C17 C12 C13 C14 -0.9(4) . . . . ? S1 C12 C13 C14 173.5(2) . . . . ? C12 C13 C14 C15 1.1(5) . . . . ? C13 C14 C15 C16 -0.1(5) . . . . ? C14 C15 C16 C17 -1.2(5) . . . . ? C13 C12 C17 C16 -0.4(4) . . . . ? S1 C12 C17 C16 -174.4(2) . . . . ? C15 C16 C17 C12 1.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.204 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.034 # Attachment '- kms5.cif' data_kms5 _database_code_depnum_ccdc_archive 'CCDC 795698' #TrackingRef '- kms5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H13 N O2' _chemical_formula_sum 'C17 H13 N O2' _chemical_formula_weight 263.28 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.738(2) _cell_length_b 9.523(5) _cell_length_c 14.954(7) _cell_angle_alpha 91.602(9) _cell_angle_beta 96.669(9) _cell_angle_gamma 94.446(9) _cell_volume 667.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1193 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 23.7 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9750 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4834 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2333 _reflns_number_gt 1712 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.0771P] 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 2333 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1334 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 1.1126(3) 0.51355(16) 0.20200(10) 0.0734(5) Uani 1 1 d . . . O2 O 1.2920(4) 0.32939(19) -0.02380(12) 0.0929(6) Uani 1 1 d . . . N1 N 0.7928(3) 0.33408(18) 0.23523(11) 0.0585(5) Uani 1 1 d . . . C2 C 0.9713(4) 0.3843(2) 0.18239(14) 0.0573(5) Uani 1 1 d . . . C3 C 1.0368(4) 0.3165(2) 0.10215(13) 0.0568(5) Uani 1 1 d . . . C4 C 0.9057(4) 0.1860(2) 0.08138(14) 0.0594(6) Uani 1 1 d . . . H4 H 0.9432 0.1375 0.0298 0.071 Uiso 1 1 calc R . . C5 C 0.5754(5) -0.0143(2) 0.12002(15) 0.0654(6) Uani 1 1 d . . . H5 H 0.6118 -0.0688 0.0707 0.078 Uiso 1 1 calc R . . C6 C 0.3905(5) -0.0666(3) 0.17542(17) 0.0723(7) Uani 1 1 d . . . H6 H 0.3001 -0.1565 0.1639 0.087 Uiso 1 1 calc R . . C7 C 0.3342(5) 0.0138(3) 0.24993(16) 0.0722(7) Uani 1 1 d . . . H7 H 0.2046 -0.0227 0.2872 0.087 Uiso 1 1 calc R . . C8 C 0.4669(5) 0.1446(3) 0.26854(14) 0.0655(6) Uani 1 1 d . . . H8 H 0.4284 0.1966 0.3186 0.079 Uiso 1 1 calc R . . C9 C 0.6617(4) 0.2022(2) 0.21278(13) 0.0543(5) Uani 1 1 d . . . C10 C 0.7137(4) 0.1223(2) 0.13638(13) 0.0553(5) Uani 1 1 d . . . C11 C 1.2381(5) 0.3821(3) 0.04501(16) 0.0697(6) Uani 1 1 d . . . H11 H 1.3290 0.4699 0.0635 0.084 Uiso 1 1 calc R . . C12 C 1.0711(5) 0.5826(2) 0.28335(15) 0.0615(6) Uani 1 1 d . . . C13 C 1.2314(5) 0.5532(3) 0.36076(18) 0.0797(7) Uani 1 1 d . . . H13 H 1.3637 0.4859 0.3607 0.096 Uiso 1 1 calc R . . C14 C 1.1948(6) 0.6246(3) 0.43924(18) 0.0861(8) Uani 1 1 d . . . H14 H 1.3016 0.6032 0.4925 0.103 Uiso 1 1 calc R . . C15 C 1.0054(6) 0.7268(3) 0.44155(16) 0.0717(7) Uani 1 1 d . . . C16 C 0.8518(6) 0.7553(3) 0.36137(17) 0.0773(7) Uani 1 1 d . . . H16 H 0.7238 0.8246 0.3606 0.093 Uiso 1 1 calc R . . C17 C 0.8825(5) 0.6837(3) 0.28185(16) 0.0725(7) Uani 1 1 d . . . H17 H 0.7763 0.7042 0.2282 0.087 Uiso 1 1 calc R . . C18 C 0.9652(7) 0.8026(3) 0.52823(18) 0.1065(10) Uani 1 1 d . . . H18A H 0.9642 0.7366 0.5756 0.160 Uiso 1 1 calc R . . H18B H 0.7873 0.8452 0.5212 0.160 Uiso 1 1 calc R . . H18C H 1.1186 0.8743 0.5433 0.160 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 0.0816(11) 0.0661(10) 0.0738(10) -0.0040(8) 0.0286(8) -0.0136(8) O2 0.1083(14) 0.0999(14) 0.0771(12) 0.0018(10) 0.0463(11) -0.0020(11) N1 0.0547(10) 0.0621(12) 0.0600(11) 0.0042(9) 0.0148(9) 0.0002(9) C2 0.0515(12) 0.0577(13) 0.0628(13) 0.0048(11) 0.0082(10) 0.0023(10) C3 0.0502(12) 0.0656(14) 0.0562(12) 0.0072(11) 0.0100(10) 0.0073(11) C4 0.0533(12) 0.0730(15) 0.0536(12) 0.0011(11) 0.0092(10) 0.0123(11) C5 0.0642(14) 0.0633(15) 0.0672(14) -0.0028(11) 0.0044(11) 0.0035(12) C6 0.0689(15) 0.0631(15) 0.0818(17) 0.0083(13) 0.0025(13) -0.0072(12) C7 0.0623(14) 0.0785(17) 0.0752(16) 0.0132(13) 0.0123(12) -0.0078(13) C8 0.0600(13) 0.0771(16) 0.0604(13) 0.0061(12) 0.0137(11) 0.0013(12) C9 0.0474(11) 0.0624(14) 0.0532(12) 0.0065(10) 0.0057(9) 0.0038(10) C10 0.0482(12) 0.0631(14) 0.0542(12) 0.0043(10) 0.0026(10) 0.0069(10) C11 0.0688(15) 0.0763(17) 0.0673(15) 0.0086(12) 0.0221(12) 0.0025(12) C12 0.0640(14) 0.0552(13) 0.0654(14) 0.0040(11) 0.0175(12) -0.0104(11) C13 0.0818(18) 0.0722(17) 0.0839(18) 0.0029(14) 0.0029(15) 0.0092(13) C14 0.095(2) 0.0844(19) 0.0743(18) 0.0028(15) -0.0058(14) 0.0013(16) C15 0.0845(17) 0.0618(15) 0.0679(16) 0.0038(12) 0.0187(13) -0.0148(13) C16 0.0859(17) 0.0713(16) 0.0789(17) 0.0080(13) 0.0238(14) 0.0104(13) C17 0.0763(16) 0.0741(17) 0.0683(16) 0.0110(13) 0.0119(12) 0.0056(13) C18 0.143(3) 0.094(2) 0.0819(19) -0.0117(16) 0.0293(18) -0.0062(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 C2 1.362(2) . ? O1 C12 1.408(3) . ? O2 C11 1.195(2) . ? N1 C2 1.297(2) . ? N1 C9 1.373(3) . ? C2 C3 1.424(3) . ? C3 C4 1.357(3) . ? C3 C11 1.469(3) . ? C4 C10 1.410(3) . ? C4 H4 0.9300 . ? C5 C6 1.351(3) . ? C5 C10 1.412(3) . ? C5 H5 0.9300 . ? C6 C7 1.397(3) . ? C6 H6 0.9300 . ? C7 C8 1.358(3) . ? C7 H7 0.9300 . ? C8 C9 1.405(3) . ? C8 H8 0.9300 . ? C9 C10 1.411(3) . ? C11 H11 0.9300 . ? C12 C13 1.357(3) . ? C12 C17 1.362(3) . ? C13 C14 1.375(3) . ? C13 H13 0.9300 . ? C14 C15 1.376(4) . ? C14 H14 0.9300 . ? C15 C16 1.374(3) . ? C15 C18 1.504(3) . ? C16 C17 1.382(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 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 C2 O1 C12 117.45(16) . . ? C2 N1 C9 116.81(18) . . ? N1 C2 O1 119.63(19) . . ? N1 C2 C3 125.8(2) . . ? O1 C2 C3 114.55(18) . . ? C4 C3 C2 116.39(19) . . ? C4 C3 C11 121.2(2) . . ? C2 C3 C11 122.4(2) . . ? C3 C4 C10 121.4(2) . . ? C3 C4 H4 119.3 . . ? C10 C4 H4 119.3 . . ? C6 C5 C10 120.6(2) . . ? C6 C5 H5 119.7 . . ? C10 C5 H5 119.7 . . ? C5 C6 C7 120.4(2) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.7(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 120.6(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? N1 C9 C8 118.29(19) . . ? N1 C9 C10 122.97(18) . . ? C8 C9 C10 118.7(2) . . ? C4 C10 C9 116.6(2) . . ? C4 C10 C5 124.4(2) . . ? C9 C10 C5 119.05(19) . . ? O2 C11 C3 123.9(2) . . ? O2 C11 H11 118.0 . . ? C3 C11 H11 118.0 . . ? C13 C12 C17 121.3(2) . . ? C13 C12 O1 119.4(2) . . ? C17 C12 O1 119.2(2) . . ? C12 C13 C14 118.8(2) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C13 C14 C15 122.2(3) . . ? C13 C14 H14 118.9 . . ? C15 C14 H14 118.9 . . ? C16 C15 C14 117.0(2) . . ? C16 C15 C18 121.4(3) . . ? C14 C15 C18 121.5(3) . . ? C15 C16 C17 121.7(3) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C12 C17 C16 118.9(2) . . ? C12 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C9 N1 C2 O1 -178.72(17) . . . . ? C9 N1 C2 C3 1.9(3) . . . . ? C12 O1 C2 N1 4.4(3) . . . . ? C12 O1 C2 C3 -176.16(19) . . . . ? N1 C2 C3 C4 -2.1(3) . . . . ? O1 C2 C3 C4 178.45(17) . . . . ? N1 C2 C3 C11 178.8(2) . . . . ? O1 C2 C3 C11 -0.7(3) . . . . ? C2 C3 C4 C10 0.4(3) . . . . ? C11 C3 C4 C10 179.58(19) . . . . ? C10 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 -0.9(3) . . . . ? C6 C7 C8 C9 0.5(3) . . . . ? C2 N1 C9 C8 -179.94(19) . . . . ? C2 N1 C9 C10 0.0(3) . . . . ? C7 C8 C9 N1 -179.15(19) . . . . ? C7 C8 C9 C10 0.9(3) . . . . ? C3 C4 C10 C9 1.1(3) . . . . ? C3 C4 C10 C5 -178.39(19) . . . . ? N1 C9 C10 C4 -1.4(3) . . . . ? C8 C9 C10 C4 178.51(18) . . . . ? N1 C9 C10 C5 178.13(18) . . . . ? C8 C9 C10 C5 -2.0(3) . . . . ? C6 C5 C10 C4 -178.9(2) . . . . ? C6 C5 C10 C9 1.6(3) . . . . ? C4 C3 C11 O2 2.8(4) . . . . ? C2 C3 C11 O2 -178.1(2) . . . . ? C2 O1 C12 C13 84.9(2) . . . . ? C2 O1 C12 C17 -99.0(2) . . . . ? C17 C12 C13 C14 1.9(4) . . . . ? O1 C12 C13 C14 178.0(2) . . . . ? C12 C13 C14 C15 -1.3(4) . . . . ? C13 C14 C15 C16 0.0(4) . . . . ? C13 C14 C15 C18 179.2(2) . . . . ? C14 C15 C16 C17 0.8(3) . . . . ? C18 C15 C16 C17 -178.4(2) . . . . ? C13 C12 C17 C16 -1.2(3) . . . . ? O1 C12 C17 C16 -177.26(19) . . . . ? C15 C16 C17 C12 -0.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.124 _refine_diff_density_min -0.097 _refine_diff_density_rms 0.027 # Attachment '- kms6.cif' data_kms6 _database_code_depnum_ccdc_archive 'CCDC 795699' #TrackingRef '- kms6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H10 N2 S' _chemical_formula_sum 'C16 H10 N2 S' _chemical_formula_weight 262.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 3.9434(11) _cell_length_b 21.648(6) _cell_length_c 14.748(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.449(5) _cell_angle_gamma 90.00 _cell_volume 1251.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1776 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 26.96 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8859 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8909 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2209 _reflns_number_gt 1930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+1.7067P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2209 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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 1.1162(2) 0.33779(4) 0.78932(5) 0.0181(2) Uani 1 1 d . . . N1 N 0.7712(6) 0.43190(11) 0.70159(17) 0.0157(6) Uani 1 1 d . . . N2 N 1.4450(7) 0.41799(12) 0.99322(19) 0.0256(7) Uani 1 1 d . . . C4 C 0.9922(8) 0.51813(15) 0.8387(2) 0.0185(7) Uani 1 1 d . . . C3 C 1.0800(8) 0.45677(14) 0.8471(2) 0.0168(7) Uani 1 1 d . . . C2 C 0.9678(8) 0.41487(14) 0.7744(2) 0.0161(7) Uani 1 1 d . . . C8 C 0.4658(8) 0.51100(15) 0.6136(2) 0.0176(7) Uani 1 1 d . . . C7 C 0.3828(8) 0.57181(15) 0.5992(2) 0.0184(7) Uani 1 1 d . . . C6 C 0.4974(8) 0.61693(15) 0.6643(2) 0.0199(7) Uani 1 1 d . . . C5 C 0.6919(8) 0.60046(14) 0.7430(2) 0.0179(7) Uani 1 1 d . . . C10 C 0.7881(8) 0.53816(14) 0.7591(2) 0.0161(7) Uani 1 1 d . . . C9 C 0.6771(8) 0.49280(14) 0.6925(2) 0.0148(7) Uani 1 1 d . . . C11 C 1.2835(8) 0.43488(14) 0.9283(2) 0.0189(7) Uani 1 1 d . . . C12 C 0.9987(8) 0.30247(14) 0.6816(2) 0.0156(7) Uani 1 1 d . . . C13 C 0.8250(8) 0.24658(15) 0.6807(2) 0.0201(7) Uani 1 1 d . . . C14 C 0.7607(9) 0.21342(16) 0.6002(2) 0.0231(8) Uani 1 1 d . . . C15 C 0.8634(9) 0.23645(15) 0.5203(2) 0.0230(8) Uani 1 1 d . . . C16 C 1.0355(8) 0.29279(15) 0.5208(2) 0.0215(7) Uani 1 1 d . . . C17 C 1.1085(8) 0.32547(15) 0.6012(2) 0.0182(7) Uani 1 1 d . . . H4 H 1.068(8) 0.5479(14) 0.886(2) 0.016(8) Uiso 1 1 d . . . H8 H 0.393(9) 0.4811(17) 0.573(2) 0.032(10) Uiso 1 1 d . . . H7 H 0.243(8) 0.5835(14) 0.547(2) 0.016(8) Uiso 1 1 d . . . H6 H 0.434(7) 0.6566(15) 0.652(2) 0.010(8) Uiso 1 1 d . . . H5 H 0.780(8) 0.6289(15) 0.787(2) 0.019(9) Uiso 1 1 d . . . H13 H 0.752(8) 0.2328(14) 0.738(2) 0.018(8) Uiso 1 1 d . . . H14 H 0.652(9) 0.1764(17) 0.599(2) 0.026(10) Uiso 1 1 d . . . H15 H 0.815(8) 0.2131(15) 0.465(2) 0.018(8) Uiso 1 1 d . . . H16 H 1.126(9) 0.3070(15) 0.467(2) 0.026(9) Uiso 1 1 d . . . H17 H 1.235(8) 0.3624(16) 0.605(2) 0.020(9) Uiso 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 0.0243(4) 0.0124(4) 0.0171(4) 0.0013(3) -0.0002(3) 0.0025(3) N1 0.0178(14) 0.0121(13) 0.0175(14) 0.0002(11) 0.0039(11) 0.0007(11) N2 0.0323(17) 0.0186(15) 0.0243(16) 0.0003(13) -0.0035(13) -0.0005(13) C4 0.0213(17) 0.0201(18) 0.0150(16) -0.0061(14) 0.0052(14) -0.0080(14) C3 0.0161(16) 0.0186(17) 0.0155(16) 0.0018(13) 0.0008(13) -0.0013(13) C2 0.0173(16) 0.0125(16) 0.0192(17) 0.0019(13) 0.0056(13) -0.0028(12) C8 0.0199(17) 0.0169(17) 0.0163(17) -0.0018(14) 0.0031(14) -0.0004(14) C7 0.0205(17) 0.0172(17) 0.0178(17) 0.0025(13) 0.0037(14) 0.0050(14) C6 0.0210(18) 0.0150(18) 0.0248(18) 0.0026(14) 0.0071(14) 0.0044(14) C5 0.0209(17) 0.0131(16) 0.0206(17) -0.0050(14) 0.0063(14) -0.0016(13) C10 0.0152(16) 0.0156(16) 0.0185(17) -0.0018(13) 0.0061(13) -0.0017(13) C9 0.0138(16) 0.0123(16) 0.0195(16) 0.0020(13) 0.0063(13) 0.0011(12) C11 0.0216(17) 0.0141(16) 0.0208(18) -0.0046(14) 0.0018(14) -0.0039(13) C12 0.0174(16) 0.0133(16) 0.0159(16) 0.0016(12) 0.0009(13) 0.0065(13) C13 0.0232(18) 0.0155(17) 0.0222(18) 0.0018(14) 0.0056(14) 0.0027(13) C14 0.0216(18) 0.0126(17) 0.035(2) -0.0018(15) 0.0008(15) -0.0023(14) C15 0.0252(18) 0.0187(18) 0.0243(19) -0.0094(15) -0.0008(14) 0.0066(15) C16 0.0223(18) 0.0216(18) 0.0206(18) 0.0034(14) 0.0029(14) 0.0066(14) C17 0.0192(17) 0.0122(17) 0.0232(18) -0.0002(13) 0.0019(14) 0.0010(13) _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 C2 1.774(3) . ? S1 C12 1.777(3) . ? N1 C2 1.305(4) . ? N1 C9 1.372(4) . ? N2 C11 1.149(4) . ? C4 C3 1.375(4) . ? C4 C10 1.415(4) . ? C4 H4 0.97(3) . ? C3 C2 1.436(4) . ? C3 C11 1.444(4) . ? C8 C7 1.367(4) . ? C8 C9 1.410(4) . ? C8 H8 0.91(4) . ? C7 C6 1.408(5) . ? C7 H7 0.93(3) . ? C6 C5 1.364(5) . ? C6 H6 0.91(3) . ? C5 C10 1.414(4) . ? C5 H5 0.93(3) . ? C10 C9 1.423(4) . ? C12 C13 1.389(4) . ? C12 C17 1.399(4) . ? C13 C14 1.386(5) . ? C13 H13 0.96(3) . ? C14 C15 1.381(5) . ? C14 H14 0.91(4) . ? C15 C16 1.395(5) . ? C15 H15 0.97(3) . ? C16 C17 1.384(4) . ? C16 H16 0.96(3) . ? C17 H17 0.94(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 C2 S1 C12 104.16(14) . . ? C2 N1 C9 118.7(3) . . ? C3 C4 C10 119.0(3) . . ? C3 C4 H4 121.4(18) . . ? C10 C4 H4 119.6(18) . . ? C4 C3 C2 119.3(3) . . ? C4 C3 C11 120.2(3) . . ? C2 C3 C11 120.5(3) . . ? N1 C2 C3 122.7(3) . . ? N1 C2 S1 121.7(2) . . ? C3 C2 S1 115.6(2) . . ? C7 C8 C9 120.4(3) . . ? C7 C8 H8 122(2) . . ? C9 C8 H8 118(2) . . ? C8 C7 C6 120.6(3) . . ? C8 C7 H7 119.9(19) . . ? C6 C7 H7 119.4(19) . . ? C5 C6 C7 120.3(3) . . ? C5 C6 H6 122.0(19) . . ? C7 C6 H6 117.6(19) . . ? C6 C5 C10 120.5(3) . . ? C6 C5 H5 123(2) . . ? C10 C5 H5 116(2) . . ? C5 C10 C4 123.3(3) . . ? C5 C10 C9 119.1(3) . . ? C4 C10 C9 117.6(3) . . ? N1 C9 C8 118.5(3) . . ? N1 C9 C10 122.5(3) . . ? C8 C9 C10 119.0(3) . . ? N2 C11 C3 179.3(4) . . ? C13 C12 C17 120.0(3) . . ? C13 C12 S1 117.6(2) . . ? C17 C12 S1 122.0(2) . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13 122.8(19) . . ? C12 C13 H13 117.0(19) . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 119(2) . . ? C13 C14 H14 121(2) . . ? C14 C15 C16 120.0(3) . . ? C14 C15 H15 119.2(19) . . ? C16 C15 H15 120.7(19) . . ? C17 C16 C15 120.3(3) . . ? C17 C16 H16 119(2) . . ? C15 C16 H16 120(2) . . ? C16 C17 C12 119.4(3) . . ? C16 C17 H17 123(2) . . ? C12 C17 H17 118(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C4 C3 C2 1.1(4) . . . . ? C10 C4 C3 C11 -179.0(3) . . . . ? C9 N1 C2 C3 2.3(4) . . . . ? C9 N1 C2 S1 -177.3(2) . . . . ? C4 C3 C2 N1 -3.2(5) . . . . ? C11 C3 C2 N1 176.9(3) . . . . ? C4 C3 C2 S1 176.4(2) . . . . ? C11 C3 C2 S1 -3.5(4) . . . . ? C12 S1 C2 N1 9.6(3) . . . . ? C12 S1 C2 C3 -170.0(2) . . . . ? C9 C8 C7 C6 -2.1(5) . . . . ? C8 C7 C6 C5 -0.3(5) . . . . ? C7 C6 C5 C10 1.6(5) . . . . ? C6 C5 C10 C4 179.3(3) . . . . ? C6 C5 C10 C9 -0.4(5) . . . . ? C3 C4 C10 C5 -178.2(3) . . . . ? C3 C4 C10 C9 1.5(4) . . . . ? C2 N1 C9 C8 179.8(3) . . . . ? C2 N1 C9 C10 0.5(4) . . . . ? C7 C8 C9 N1 -176.1(3) . . . . ? C7 C8 C9 C10 3.2(4) . . . . ? C5 C10 C9 N1 177.3(3) . . . . ? C4 C10 C9 N1 -2.4(4) . . . . ? C5 C10 C9 C8 -1.9(4) . . . . ? C4 C10 C9 C8 178.3(3) . . . . ? C2 S1 C12 C13 -129.7(2) . . . . ? C2 S1 C12 C17 57.6(3) . . . . ? C17 C12 C13 C14 0.1(5) . . . . ? S1 C12 C13 C14 -172.7(3) . . . . ? C12 C13 C14 C15 -1.2(5) . . . . ? C13 C14 C15 C16 0.7(5) . . . . ? C14 C15 C16 C17 0.9(5) . . . . ? C15 C16 C17 C12 -2.0(5) . . . . ? C13 C12 C17 C16 1.5(5) . . . . ? S1 C12 C17 C16 174.0(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.372 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.065 # Attachment '- kms7.cif' data_kms7 _database_code_depnum_ccdc_archive 'CCDC 795700' #TrackingRef '- kms7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 N2 O' _chemical_formula_sum 'C11 H8 N2 O' _chemical_formula_weight 184.19 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 P21/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 3.989(2) _cell_length_b 21.214(11) _cell_length_c 11.076(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.855(9) _cell_angle_gamma 90.00 _cell_volume 928.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1553 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 23.60 _exptl_crystal_description 'thin needle' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9734 _exptl_absorpt_correction_T_max 0.9969 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8496 _diffrn_reflns_av_R_equivalents 0.1589 _diffrn_reflns_av_sigmaI/netI 0.0914 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1634 _reflns_number_gt 1077 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1159P)^2^+1.2770P] 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 1634 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1519 _refine_ls_R_factor_gt 0.1078 _refine_ls_wR_factor_ref 0.2789 _refine_ls_wR_factor_gt 0.2525 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.6647(9) 0.04828(15) 0.9011(3) 0.0499(10) Uani 1 1 d . . . N1 N 0.4051(9) 0.14236(18) 0.8428(3) 0.0374(10) Uani 1 1 d . . . N2 N 0.5238(15) -0.0614(3) 0.6667(5) 0.0859(18) Uani 1 1 d . . . C4 C 0.1553(12) 0.0879(2) 0.6172(4) 0.0481(13) Uani 1 1 d . . . H4 H 0.0725 0.0691 0.5433 0.058 Uiso 1 1 calc R . . C3 C 0.3568(12) 0.0542(2) 0.7051(4) 0.0447(12) Uani 1 1 d . . . C2 C 0.4710(11) 0.0842(2) 0.8172(4) 0.0391(11) Uani 1 1 d . . . C8 C 0.1384(12) 0.2400(2) 0.7791(4) 0.0465(12) Uani 1 1 d . . . H8 H 0.2249 0.2578 0.8536 0.056 Uiso 1 1 calc R . . C7 C -0.0568(13) 0.2755(3) 0.6920(5) 0.0562(14) Uani 1 1 d . . . H7 H -0.1026 0.3173 0.7095 0.067 Uiso 1 1 calc R . . C6 C -0.1874(13) 0.2511(3) 0.5788(5) 0.0543(14) Uani 1 1 d . . . H6 H -0.3150 0.2763 0.5211 0.065 Uiso 1 1 calc R . . C5 C -0.1258(12) 0.1896(2) 0.5537(4) 0.0483(13) Uani 1 1 d . . . H5 H -0.2168 0.1726 0.4789 0.058 Uiso 1 1 calc R . . C10 C 0.0751(11) 0.1511(2) 0.6400(4) 0.0395(12) Uani 1 1 d . . . C9 C 0.2056(10) 0.1763(2) 0.7541(4) 0.0361(11) Uani 1 1 d . . . C11 C 0.4514(14) -0.0104(3) 0.6855(5) 0.0552(14) Uani 1 1 d . . . C12 C 0.7887(13) 0.0773(2) 1.0148(4) 0.0504(13) Uani 1 1 d . . . H12A H 0.9226 0.1134 1.0006 0.076 Uiso 1 1 calc R . . H12B H 0.9254 0.0477 1.0653 0.076 Uiso 1 1 calc R . . H12C H 0.6013 0.0902 1.0549 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 O1 0.054(2) 0.048(2) 0.045(2) -0.0034(15) -0.0036(16) 0.0042(16) N1 0.029(2) 0.047(2) 0.034(2) 0.0001(17) -0.0005(16) -0.0041(16) N2 0.101(4) 0.062(3) 0.093(4) -0.027(3) 0.011(3) 0.003(3) C4 0.042(3) 0.065(3) 0.038(3) -0.010(2) 0.004(2) -0.021(2) C3 0.039(3) 0.052(3) 0.045(3) -0.008(2) 0.009(2) -0.012(2) C2 0.030(2) 0.046(3) 0.041(3) 0.005(2) 0.004(2) -0.007(2) C8 0.041(3) 0.058(3) 0.039(3) -0.004(2) 0.001(2) 0.002(2) C7 0.047(3) 0.060(3) 0.060(4) 0.011(3) 0.002(3) 0.006(2) C6 0.041(3) 0.068(4) 0.051(3) 0.014(3) -0.005(2) 0.000(2) C5 0.047(3) 0.069(4) 0.026(3) 0.005(2) -0.008(2) -0.015(2) C10 0.030(2) 0.058(3) 0.032(3) -0.001(2) 0.0058(19) -0.015(2) C9 0.023(2) 0.050(3) 0.036(3) 0.007(2) 0.0060(19) -0.0029(19) C11 0.055(3) 0.055(3) 0.056(3) -0.016(3) 0.008(3) -0.007(3) C12 0.047(3) 0.059(3) 0.043(3) 0.000(2) -0.001(2) 0.003(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 C2 1.358(5) . ? O1 C12 1.428(6) . ? N1 C2 1.301(6) . ? N1 C9 1.380(5) . ? N2 C11 1.146(7) . ? C4 C3 1.375(7) . ? C4 C10 1.410(7) . ? C4 H4 0.9300 . ? C3 C2 1.414(6) . ? C3 C11 1.445(7) . ? C8 C7 1.379(6) . ? C8 C9 1.411(6) . ? C8 H8 0.9300 . ? C7 C6 1.390(7) . ? C7 H7 0.9300 . ? C6 C5 1.364(7) . ? C6 H6 0.9300 . ? C5 C10 1.418(6) . ? C5 H5 0.9300 . ? C10 C9 1.405(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C2 O1 C12 117.3(4) . . ? C2 N1 C9 117.0(4) . . ? C3 C4 C10 119.6(4) . . ? C3 C4 H4 120.2 . . ? C10 C4 H4 120.2 . . ? C4 C3 C2 118.3(4) . . ? C4 C3 C11 121.7(4) . . ? C2 C3 C11 120.0(4) . . ? N1 C2 O1 119.7(4) . . ? N1 C2 C3 124.6(4) . . ? O1 C2 C3 115.6(4) . . ? C7 C8 C9 119.4(4) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C7 C6 122.2(5) . . ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? C5 C6 C7 119.0(5) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C6 C5 C10 120.9(4) . . ? C6 C5 H5 119.5 . . ? C10 C5 H5 119.5 . . ? C9 C10 C4 117.2(4) . . ? C9 C10 C5 119.5(4) . . ? C4 C10 C5 123.2(4) . . ? N1 C9 C10 123.2(4) . . ? N1 C9 C8 117.8(4) . . ? C10 C9 C8 118.9(4) . . ? N2 C11 C3 178.2(6) . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C10 C4 C3 C2 1.3(6) . . . . ? C10 C4 C3 C11 -178.8(4) . . . . ? C9 N1 C2 O1 -179.6(4) . . . . ? C9 N1 C2 C3 0.9(6) . . . . ? C12 O1 C2 N1 -0.3(6) . . . . ? C12 O1 C2 C3 179.2(4) . . . . ? C4 C3 C2 N1 -1.5(7) . . . . ? C11 C3 C2 N1 178.7(4) . . . . ? C4 C3 C2 O1 179.0(4) . . . . ? C11 C3 C2 O1 -0.8(6) . . . . ? C9 C8 C7 C6 -0.8(8) . . . . ? C8 C7 C6 C5 1.2(8) . . . . ? C7 C6 C5 C10 -1.5(7) . . . . ? C3 C4 C10 C9 -0.7(6) . . . . ? C3 C4 C10 C5 178.9(4) . . . . ? C6 C5 C10 C9 1.6(7) . . . . ? C6 C5 C10 C4 -178.0(5) . . . . ? C2 N1 C9 C10 -0.2(6) . . . . ? C2 N1 C9 C8 -178.5(4) . . . . ? C4 C10 C9 N1 0.1(6) . . . . ? C5 C10 C9 N1 -179.5(4) . . . . ? C4 C10 C9 C8 178.3(4) . . . . ? C5 C10 C9 C8 -1.2(6) . . . . ? C7 C8 C9 N1 179.2(4) . . . . ? C7 C8 C9 C10 0.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.363 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.076 # Attachment '- kms11.cif' data_kms11 _database_code_depnum_ccdc_archive 'CCDC 795701' #TrackingRef '- kms11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H5 N5' _chemical_formula_sum 'C10 H5 N5' _chemical_formula_weight 195.19 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 7.353(4) _cell_length_b 13.472(8) _cell_length_c 9.327(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.714(10) _cell_angle_gamma 90.00 _cell_volume 875.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 437 _cell_measurement_theta_min 2.757 _cell_measurement_theta_max 19.06 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9702 _exptl_absorpt_correction_T_max 0.9966 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4260 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1545 _reflns_number_gt 994 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+0.1648P] 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 1545 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1240 _refine_ls_R_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.1688 _refine_ls_wR_factor_gt 0.1505 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.7528(4) 0.8514(2) 0.4778(3) 0.0342(8) Uani 1 1 d . . . N2 N 0.6259(5) 0.7373(2) 0.3107(3) 0.0466(9) Uani 1 1 d . . . N3 N 0.7465(5) 0.6961(2) 0.4390(4) 0.0521(9) Uani 1 1 d . . . N4 N 0.8244(4) 0.7630(2) 0.5413(3) 0.0450(8) Uani 1 1 d . . . N5 N 0.3042(5) 0.8810(3) -0.0206(4) 0.0627(11) Uani 1 1 d . . . C2 C 0.6318(5) 0.8336(3) 0.3372(4) 0.0358(9) Uani 1 1 d . . . C3 C 0.5396(5) 0.9158(3) 0.2451(4) 0.0342(9) Uani 1 1 d . . . C4 C 0.5775(5) 1.0082(3) 0.3020(4) 0.0398(9) Uani 1 1 d . . . H4 H 0.5196 1.0620 0.2422 0.048 Uiso 1 1 calc R . . C5 C 0.7471(5) 1.1209(3) 0.5149(4) 0.0457(10) Uani 1 1 d . . . H5 H 0.6911 1.1760 0.4574 0.055 Uiso 1 1 calc R . . C6 C 0.8694(6) 1.1342(3) 0.6592(4) 0.0499(11) Uani 1 1 d . . . H6 H 0.8959 1.1980 0.6985 0.060 Uiso 1 1 calc R . . C7 C 0.9538(5) 1.0533(3) 0.7474(4) 0.0477(11) Uani 1 1 d . . . H7 H 1.0353 1.0634 0.8456 0.057 Uiso 1 1 calc R . . C8 C 0.9187(5) 0.9581(3) 0.6914(4) 0.0418(10) Uani 1 1 d . . . H8 H 0.9763 0.9038 0.7500 0.050 Uiso 1 1 calc R . . C9 C 0.7953(5) 0.9455(2) 0.5453(4) 0.0346(9) Uani 1 1 d . . . C10 C 0.7051(5) 1.0259(2) 0.4526(4) 0.0339(9) Uani 1 1 d . . . C11 C 0.4091(5) 0.8962(3) 0.0961(4) 0.0428(10) 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 N1 0.0329(18) 0.0331(18) 0.0343(17) 0.0035(13) 0.0077(14) 0.0024(13) N2 0.056(2) 0.0337(19) 0.0453(19) -0.0022(15) 0.0086(17) -0.0022(15) N3 0.063(2) 0.0325(19) 0.055(2) 0.0059(16) 0.0108(18) 0.0014(16) N4 0.049(2) 0.0367(19) 0.0474(19) 0.0073(16) 0.0121(16) 0.0073(16) N5 0.061(2) 0.072(3) 0.042(2) 0.0018(18) -0.0032(19) 0.0009(19) C2 0.036(2) 0.035(2) 0.037(2) -0.0023(16) 0.0109(17) -0.0069(16) C3 0.030(2) 0.039(2) 0.0308(19) 0.0039(16) 0.0058(16) -0.0020(16) C4 0.044(2) 0.037(2) 0.037(2) 0.0061(17) 0.0112(18) 0.0020(18) C5 0.048(3) 0.033(2) 0.056(3) -0.0010(18) 0.017(2) -0.0045(18) C6 0.049(3) 0.049(3) 0.052(3) -0.017(2) 0.018(2) -0.010(2) C7 0.041(3) 0.061(3) 0.039(2) -0.010(2) 0.0101(19) -0.005(2) C8 0.034(2) 0.046(2) 0.040(2) -0.0015(18) 0.0042(18) 0.0046(18) C9 0.027(2) 0.036(2) 0.039(2) -0.0008(17) 0.0086(17) -0.0026(16) C10 0.031(2) 0.035(2) 0.036(2) 0.0027(16) 0.0121(17) -0.0020(16) C11 0.041(2) 0.045(2) 0.038(2) 0.0049(18) 0.008(2) 0.0040(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 N1 C2 1.349(4) . ? N1 N4 1.358(4) . ? N1 C9 1.406(4) . ? N2 C2 1.320(4) . ? N2 N3 1.358(4) . ? N3 N4 1.304(4) . ? N5 C11 1.133(4) . ? C2 C3 1.431(5) . ? C3 C4 1.347(5) . ? C3 C11 1.437(5) . ? C4 C10 1.437(5) . ? C5 C6 1.370(5) . ? C5 C10 1.399(5) . ? C6 C7 1.387(5) . ? C7 C8 1.377(5) . ? C8 C9 1.384(5) . ? C9 C10 1.411(5) . ? 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 C2 N1 N4 108.1(3) . . ? C2 N1 C9 125.3(3) . . ? N4 N1 C9 126.6(3) . . ? C2 N2 N3 105.3(3) . . ? N4 N3 N2 111.8(3) . . ? N3 N4 N1 105.6(3) . . ? N2 C2 N1 109.2(3) . . ? N2 C2 C3 131.9(3) . . ? N1 C2 C3 118.9(3) . . ? C4 C3 C2 118.7(3) . . ? C4 C3 C11 122.7(3) . . ? C2 C3 C11 118.6(3) . . ? C3 C4 C10 121.7(3) . . ? C6 C5 C10 121.0(4) . . ? C5 C6 C7 120.5(4) . . ? C8 C7 C6 120.9(4) . . ? C7 C8 C9 118.1(3) . . ? C8 C9 N1 122.2(3) . . ? C8 C9 C10 122.7(3) . . ? N1 C9 C10 115.1(3) . . ? C5 C10 C9 116.8(3) . . ? C5 C10 C4 123.0(3) . . ? C9 C10 C4 120.2(3) . . ? N5 C11 C3 179.0(4) . . ? 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 C2 N2 N3 N4 0.1(4) . . . . ? N2 N3 N4 N1 -0.2(4) . . . . ? C2 N1 N4 N3 0.2(4) . . . . ? C9 N1 N4 N3 -180.0(3) . . . . ? N3 N2 C2 N1 0.1(4) . . . . ? N3 N2 C2 C3 178.6(4) . . . . ? N4 N1 C2 N2 -0.2(4) . . . . ? C9 N1 C2 N2 -180.0(3) . . . . ? N4 N1 C2 C3 -178.9(3) . . . . ? C9 N1 C2 C3 1.3(5) . . . . ? N2 C2 C3 C4 -178.1(4) . . . . ? N1 C2 C3 C4 0.2(5) . . . . ? N2 C2 C3 C11 2.3(6) . . . . ? N1 C2 C3 C11 -179.3(3) . . . . ? C2 C3 C4 C10 -1.0(5) . . . . ? C11 C3 C4 C10 178.5(3) . . . . ? C10 C5 C6 C7 -0.3(6) . . . . ? C5 C6 C7 C8 0.8(6) . . . . ? C6 C7 C8 C9 -0.7(6) . . . . ? C7 C8 C9 N1 179.1(3) . . . . ? C7 C8 C9 C10 0.0(5) . . . . ? C2 N1 C9 C8 178.9(3) . . . . ? N4 N1 C9 C8 -0.9(5) . . . . ? C2 N1 C9 C10 -2.0(5) . . . . ? N4 N1 C9 C10 178.3(3) . . . . ? C6 C5 C10 C9 -0.3(5) . . . . ? C6 C5 C10 C4 179.9(3) . . . . ? C8 C9 C10 C5 0.4(5) . . . . ? N1 C9 C10 C5 -178.7(3) . . . . ? C8 C9 C10 C4 -179.7(3) . . . . ? N1 C9 C10 C4 1.1(5) . . . . ? C3 C4 C10 C5 -179.9(4) . . . . ? C3 C4 C10 C9 0.3(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.231 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.051