# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Steve Archibald' _publ_contact_author_email S.J.ARCHIBALD@HULL.AC.UK _publ_section_title ; Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives ; loop_ _publ_author_name 'Steve Archibald' 'Ross Boyle' 'Sushil C Jha' 'Jon D Silversides' # Attachment '1.cif' data_sja13_06 _database_code_depnum_ccdc_archive 'CCDC 756015' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H8 N2 O S' _chemical_formula_sum 'C6 H8 N2 O S' _chemical_formula_weight 156.20 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' 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' 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 9.3380(13) _cell_length_b 6.3930(5) _cell_length_c 13.1620(18) _cell_angle_alpha 90.00 _cell_angle_beta 108.753(11) _cell_angle_gamma 90.00 _cell_volume 744.03(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 233 _cell_measurement_theta_min 7.99 _cell_measurement_theta_max 61.82 _exptl_crystal_description lathe _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.364 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS-II image plate' _diffrn_measurement_method '\w scans, 135 frames at 1\% intervals, exposure time 1 minute' _diffrn_reflns_number 7718 _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 34.74 _reflns_number_total 3169 _reflns_number_gt 2073 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'SHELXL97(Sheldrick, 1997) and WinGX (Farrugia, 1999)' _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^)+(0.0517P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3169 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.004 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 C1 C 0.13780(13) 0.1999(2) 0.07463(8) 0.0200(2) Uani 1 1 d . . . C2 C 0.29213(13) -0.0241(2) 0.02251(9) 0.0223(2) Uani 1 1 d . . . C3 C 0.27105(14) 0.1703(2) -0.04563(10) 0.0257(3) Uani 1 1 d . . . H3A H 0.3688 0.2405 -0.0367 0.031 Uiso 1 1 calc R . . H3B H 0.2211 0.1379 -0.1225 0.031 Uiso 1 1 calc R . . C4 C 0.19422(14) -0.1506(2) 0.16710(10) 0.0234(2) Uani 1 1 d . . . H4A H 0.1968 -0.2904 0.1355 0.028 Uiso 1 1 calc R . . H4B H 0.0942 -0.1343 0.1772 0.028 Uiso 1 1 calc R . . C5 C 0.31408(15) -0.1412(2) 0.27440(10) 0.0263(2) Uani 1 1 d . . . H5 H 0.3064 -0.2392 0.3267 0.032 Uiso 1 1 calc R . . C6 C 0.42817(18) -0.0120(3) 0.30344(11) 0.0357(3) Uani 1 1 d . . . H6A H 0.4409 0.0890 0.2541 0.043 Uiso 1 1 calc R . . H6B H 0.4985 -0.0189 0.3739 0.043 Uiso 1 1 calc R . . N1 N 0.20949(12) 0.00770(16) 0.09194(8) 0.02023(19) Uani 1 1 d . . . N2 N 0.17443(12) 0.29727(18) -0.00304(8) 0.0246(2) Uani 1 1 d . . . H2 H 0.1436 0.4240 -0.0259 0.030 Uiso 1 1 calc R . . O1 O 0.36503(11) -0.17892(16) 0.01976(7) 0.0295(2) Uani 1 1 d . . . S1 S 0.02430(4) 0.28840(6) 0.14060(2) 0.02541(9) 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 C1 0.0187(4) 0.0224(5) 0.0187(4) -0.0002(4) 0.0060(4) 0.0004(4) C2 0.0216(5) 0.0276(6) 0.0176(4) -0.0008(4) 0.0062(4) 0.0029(4) C3 0.0259(5) 0.0316(7) 0.0224(5) 0.0063(5) 0.0117(4) 0.0071(5) C4 0.0274(6) 0.0197(5) 0.0237(5) 0.0024(4) 0.0091(4) -0.0028(5) C5 0.0335(6) 0.0260(6) 0.0198(5) 0.0040(4) 0.0091(4) 0.0040(5) C6 0.0390(8) 0.0341(8) 0.0266(6) -0.0024(5) 0.0001(5) 0.0000(6) N1 0.0230(4) 0.0210(5) 0.0177(4) 0.0014(3) 0.0078(3) 0.0018(4) N2 0.0270(5) 0.0249(5) 0.0247(4) 0.0070(4) 0.0121(4) 0.0054(4) O1 0.0306(5) 0.0320(5) 0.0268(4) 0.0003(4) 0.0102(3) 0.0111(4) S1 0.02727(15) 0.02810(16) 0.02446(14) 0.00076(12) 0.01335(11) 0.00524(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 C1 N2 1.3320(15) . ? C1 N1 1.3827(16) . ? C1 S1 1.6700(11) . ? C2 O1 1.2082(15) . ? C2 N1 1.3876(14) . ? C2 C3 1.5081(18) . ? C3 N2 1.4535(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.4537(15) . ? C4 C5 1.4948(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.304(2) . ? C5 H5 0.9500 . ? C6 H6A 0.9500 . ? C6 H6B 0.9500 . ? N2 H2 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 108.15(10) . . ? N2 C1 S1 127.10(10) . . ? N1 C1 S1 124.75(9) . . ? O1 C2 N1 125.31(12) . . ? O1 C2 C3 128.62(11) . . ? N1 C2 C3 106.07(10) . . ? N2 C3 C2 102.09(9) . . ? N2 C3 H3A 111.4 . . ? C2 C3 H3A 111.4 . . ? N2 C3 H3B 111.4 . . ? C2 C3 H3B 111.4 . . ? H3A C3 H3B 109.2 . . ? N1 C4 C5 114.05(11) . . ? N1 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? N1 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C4 126.52(12) . . ? C6 C5 H5 116.7 . . ? C4 C5 H5 116.7 . . ? C5 C6 H6A 120.0 . . ? C5 C6 H6B 120.0 . . ? H6A C6 H6B 120.0 . . ? C1 N1 C2 111.35(10) . . ? C1 N1 C4 125.62(9) . . ? C2 N1 C4 122.89(10) . . ? C1 N2 C3 112.29(11) . . ? C1 N2 H2 123.9 . . ? C3 N2 H2 123.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 N2 -179.32(13) . . . . ? N1 C2 C3 N2 0.64(13) . . . . ? N1 C4 C5 C6 -1.9(2) . . . . ? N2 C1 N1 C2 -1.44(14) . . . . ? S1 C1 N1 C2 178.04(9) . . . . ? N2 C1 N1 C4 -177.32(11) . . . . ? S1 C1 N1 C4 2.16(17) . . . . ? O1 C2 N1 C1 -179.61(12) . . . . ? C3 C2 N1 C1 0.43(14) . . . . ? O1 C2 N1 C4 -3.6(2) . . . . ? C3 C2 N1 C4 176.44(11) . . . . ? C5 C4 N1 C1 -94.53(14) . . . . ? C5 C4 N1 C2 90.05(14) . . . . ? N1 C1 N2 C3 1.91(14) . . . . ? S1 C1 N2 C3 -177.56(10) . . . . ? C2 C3 N2 C1 -1.58(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 S1 0.88 2.57 3.4026(12) 158.6 3_565 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 34.74 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.397 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.067 # Attachment '2.cif' data_sja14_06 _database_code_depnum_ccdc_archive 'CCDC 756016' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; __chemical_formula_moiety 'C13 H16 N2 O S' _chemical_formula_sum 'C13 H16 N2 O S' _chemical_formula_weight 248.34 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' 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' 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 5.0267(9) _cell_length_b 11.2601(12) _cell_length_c 22.199(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.545(14) _cell_angle_gamma 90.00 _cell_volume 1252.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 179 _cell_measurement_theta_min 6.68 _cell_measurement_theta_max 50.98 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.244 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS-II image plate' _diffrn_measurement_method '\w scans, 146 frames at 2\% intervals, exposure time 3 minutes' _diffrn_reflns_number 27326 _diffrn_reflns_av_R_equivalents 0.1370 _diffrn_reflns_av_sigmaI/netI 0.1539 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 34.76 _reflns_number_total 5327 _reflns_number_gt 2035 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'SHELXL97(Sheldrick, 1997) and WinGX (Farrugia, 1999)' _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^)+(0.0581P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.023(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5327 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1815 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 0.853 _refine_ls_restrained_S_all 0.853 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.002 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 C1 C 0.2053(4) 0.45686(18) 0.41568(8) 0.0243(4) Uani 1 1 d . . . C2 C -0.1402(4) 0.3279(2) 0.39580(9) 0.0267(4) Uani 1 1 d . . . C3 C -0.0351(4) 0.3105(2) 0.46097(8) 0.0263(4) Uani 1 1 d . . . H3 H -0.1708 0.3410 0.4877 0.032 Uiso 1 1 calc R . . C4 C -0.0524(5) 0.4711(2) 0.31309(8) 0.0275(5) Uani 1 1 d . . . H4A H -0.0537 0.5586 0.3172 0.033 Uiso 1 1 calc R . . H4B H -0.2340 0.4461 0.2977 0.033 Uiso 1 1 calc R . . C5 C 0.1405(4) 0.4376(2) 0.26746(8) 0.0257(4) Uani 1 1 d . . . C6 C 0.2286(5) 0.5235(2) 0.22935(9) 0.0308(5) Uani 1 1 d . . . H6 H 0.1698 0.6032 0.2327 0.037 Uiso 1 1 calc R . . C7 C 0.4023(5) 0.4942(2) 0.18623(10) 0.0367(6) Uani 1 1 d . . . H7 H 0.4627 0.5540 0.1604 0.044 Uiso 1 1 calc R . . C8 C 0.4877(5) 0.3788(3) 0.18064(9) 0.0377(6) Uani 1 1 d . . . H8 H 0.6075 0.3589 0.1512 0.045 Uiso 1 1 calc R . . C9 C 0.3979(5) 0.2925(2) 0.21817(10) 0.0361(5) Uani 1 1 d . . . H9 H 0.4543 0.2126 0.2142 0.043 Uiso 1 1 calc R . . C10 C 0.2267(5) 0.3217(2) 0.26140(9) 0.0303(5) Uani 1 1 d . . . H10 H 0.1672 0.2617 0.2873 0.036 Uiso 1 1 calc R . . C11 C 0.0282(5) 0.1807(2) 0.47779(9) 0.0282(5) Uani 1 1 d . . . H11 H -0.1443 0.1362 0.4754 0.034 Uiso 1 1 calc R . . C12 C 0.2058(5) 0.1229(2) 0.43395(11) 0.0358(5) Uani 1 1 d . . . H12A H 0.1212 0.1292 0.3928 0.054 Uiso 1 1 calc R . . H12B H 0.2314 0.0389 0.4445 0.054 Uiso 1 1 calc R . . H12C H 0.3792 0.1631 0.4363 0.054 Uiso 1 1 calc R . . C13 C 0.1496(6) 0.1732(2) 0.54259(10) 0.0417(6) Uani 1 1 d . . . H13A H 0.0299 0.2114 0.5695 0.062 Uiso 1 1 calc R . . H13B H 0.3226 0.2138 0.5460 0.062 Uiso 1 1 calc R . . H13C H 0.1744 0.0897 0.5541 0.062 Uiso 1 1 calc R . . N1 N 0.0096(4) 0.41817(16) 0.37311(7) 0.0248(4) Uani 1 1 d . . . N2 N 0.1922(4) 0.39063(16) 0.46497(7) 0.0262(4) Uani 1 1 d . . . H2 H 0.3087 0.3949 0.4966 0.031 Uiso 1 1 calc R . . O1 O -0.3186(3) 0.27485(15) 0.36817(7) 0.0347(4) Uani 1 1 d . . . S1 S 0.41270(12) 0.56913(5) 0.40554(2) 0.02792(15) 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 C1 0.0254(11) 0.0260(11) 0.0216(8) -0.0021(7) 0.0027(7) 0.0013(8) C2 0.0245(11) 0.0285(11) 0.0272(9) 0.0002(8) 0.0028(8) -0.0023(9) C3 0.0272(11) 0.0298(11) 0.0224(9) -0.0002(8) 0.0043(8) -0.0031(9) C4 0.0272(11) 0.0299(11) 0.0250(9) 0.0035(8) -0.0005(8) 0.0007(9) C5 0.0247(10) 0.0294(10) 0.0220(8) 0.0004(8) -0.0039(7) -0.0030(10) C6 0.0351(13) 0.0302(12) 0.0270(9) 0.0026(8) 0.0009(9) 0.0015(10) C7 0.0393(15) 0.0456(15) 0.0255(10) 0.0087(9) 0.0050(9) -0.0008(12) C8 0.0351(14) 0.0551(16) 0.0229(10) -0.0049(9) 0.0026(9) 0.0073(12) C9 0.0383(14) 0.0351(13) 0.0339(11) -0.0083(9) -0.0024(10) 0.0059(11) C10 0.0339(13) 0.0278(11) 0.0286(10) 0.0009(8) -0.0016(9) -0.0047(10) C11 0.0284(11) 0.0279(11) 0.0282(9) 0.0037(8) 0.0019(8) -0.0068(9) C12 0.0364(14) 0.0304(12) 0.0410(12) -0.0002(9) 0.0060(10) -0.0030(10) C13 0.0557(17) 0.0362(13) 0.0318(11) 0.0084(10) -0.0046(11) -0.0088(13) N1 0.0238(9) 0.0281(9) 0.0225(7) 0.0000(7) 0.0013(6) -0.0030(8) N2 0.0302(10) 0.0272(9) 0.0209(7) 0.0009(6) -0.0010(7) -0.0071(8) O1 0.0304(9) 0.0396(10) 0.0330(8) 0.0023(7) -0.0048(7) -0.0114(8) S1 0.0330(3) 0.0268(3) 0.0238(2) 0.0006(2) 0.00149(18) -0.0076(3) _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 C1 N2 1.330(3) . ? C1 N1 1.380(3) . ? C1 S1 1.665(2) . ? C2 O1 1.204(3) . ? C2 N1 1.383(3) . ? C2 C3 1.513(3) . ? C3 N2 1.453(3) . ? C3 C11 1.536(3) . ? C3 H3 1.0000 . ? C4 N1 1.470(2) . ? C4 C5 1.505(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.381(3) . ? C5 C10 1.385(3) . ? C6 C7 1.385(3) . ? C6 H6 0.9500 . ? C7 C8 1.377(4) . ? C7 H7 0.9500 . ? C8 C9 1.379(4) . ? C8 H8 0.9500 . ? C9 C10 1.379(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.518(3) . ? C11 C13 1.520(3) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N2 H2 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 107.89(18) . . ? N2 C1 S1 127.54(16) . . ? N1 C1 S1 124.56(15) . . ? O1 C2 N1 125.74(18) . . ? O1 C2 C3 127.7(2) . . ? N1 C2 C3 106.52(17) . . ? N2 C3 C2 101.04(16) . . ? N2 C3 C11 115.41(18) . . ? C2 C3 C11 113.93(17) . . ? N2 C3 H3 108.7 . . ? C2 C3 H3 108.7 . . ? C11 C3 H3 108.7 . . ? N1 C4 C5 114.01(18) . . ? N1 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? N1 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C10 118.8(2) . . ? C6 C5 C4 119.5(2) . . ? C10 C5 C4 121.65(19) . . ? C5 C6 C7 120.4(2) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.4(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 119.4(2) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C5 120.6(2) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? C12 C11 C13 111.8(2) . . ? C12 C11 C3 111.94(17) . . ? C13 C11 C3 110.05(18) . . ? C12 C11 H11 107.6 . . ? C13 C11 H11 107.6 . . ? C3 C11 H11 107.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C1 N1 C2 111.21(16) . . ? C1 N1 C4 125.53(18) . . ? C2 N1 C4 123.05(17) . . ? C1 N2 C3 112.83(17) . . ? C1 N2 H2 123.6 . . ? C3 N2 H2 123.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 N2 174.3(2) . . . . ? N1 C2 C3 N2 -5.7(2) . . . . ? O1 C2 C3 C11 49.9(3) . . . . ? N1 C2 C3 C11 -130.1(2) . . . . ? N1 C4 C5 C6 -137.2(2) . . . . ? N1 C4 C5 C10 44.7(3) . . . . ? C10 C5 C6 C7 -0.6(3) . . . . ? C4 C5 C6 C7 -178.8(2) . . . . ? C5 C6 C7 C8 0.4(4) . . . . ? C6 C7 C8 C9 0.3(4) . . . . ? C7 C8 C9 C10 -0.8(4) . . . . ? C8 C9 C10 C5 0.6(4) . . . . ? C6 C5 C10 C9 0.1(3) . . . . ? C4 C5 C10 C9 178.2(2) . . . . ? N2 C3 C11 C12 -65.0(2) . . . . ? C2 C3 C11 C12 51.3(3) . . . . ? N2 C3 C11 C13 59.9(2) . . . . ? C2 C3 C11 C13 176.2(2) . . . . ? N2 C1 N1 C2 2.2(2) . . . . ? S1 C1 N1 C2 -176.60(16) . . . . ? N2 C1 N1 C4 177.06(19) . . . . ? S1 C1 N1 C4 -1.7(3) . . . . ? O1 C2 N1 C1 -177.5(2) . . . . ? C3 C2 N1 C1 2.5(2) . . . . ? O1 C2 N1 C4 7.5(4) . . . . ? C3 C2 N1 C4 -172.52(18) . . . . ? C5 C4 N1 C1 77.6(3) . . . . ? C5 C4 N1 C2 -108.1(2) . . . . ? N1 C1 N2 C3 -6.3(2) . . . . ? S1 C1 N2 C3 172.41(16) . . . . ? C2 C3 N2 C1 7.4(2) . . . . ? C11 C3 N2 C1 130.82(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 S1 0.88 2.52 3.3925(19) 170.3 3_666 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 34.76 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.490 _refine_diff_density_min -0.845 _refine_diff_density_rms 0.091 # Attachment '3.cif' data_sja15_06 _database_code_depnum_ccdc_archive 'CCDC 756017' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C9 H8 N2 O S' _chemical_formula_sum 'C9 H8 N2 O S' _chemical_formula_weight 192.23 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' 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' 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 12.377(4) _cell_length_b 5.6900(12) _cell_length_c 12.515(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.27(3) _cell_angle_gamma 90.00 _cell_volume 881.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 292 _cell_measurement_theta_min 8.69 _cell_measurement_theta_max 67.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.323 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS-II image plate' _diffrn_measurement_method '\w scans, 65 frames at 2\% intervals, exposure time 2 minutes' _diffrn_reflns_number 8162 _diffrn_reflns_av_R_equivalents 0.0992 _diffrn_reflns_av_sigmaI/netI 0.0935 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 34.75 _reflns_number_total 3714 _reflns_number_gt 1498 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'SHELXL97(Sheldrick, 1997) and WinGX (Farrugia, 1999)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.43(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3714 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2063 _refine_ls_R_factor_gt 0.1199 _refine_ls_wR_factor_ref 0.4126 _refine_ls_wR_factor_gt 0.3058 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 C1 C 0.1333(3) -0.1950(8) 0.5927(3) 0.0504(10) Uani 1 1 d . . . C2 C 0.2446(4) -0.5016(8) 0.5502(3) 0.0485(10) Uani 1 1 d . . . C3 C 0.1627(4) -0.4737(8) 0.4613(3) 0.0516(10) Uani 1 1 d . . . H3A H 0.1975 -0.4371 0.3928 0.062 Uiso 1 1 calc R . . H3B H 0.1179 -0.6168 0.4525 0.062 Uiso 1 1 calc R . . C4 C 0.2877(3) -0.2945(8) 0.7194(3) 0.0448(9) Uani 1 1 d . . . C5 C 0.2879(4) -0.4674(8) 0.7974(3) 0.0503(10) Uani 1 1 d . . . H5 H 0.2417 -0.6002 0.7906 0.060 Uiso 1 1 calc R . . C6 C 0.3567(4) -0.4429(8) 0.8853(3) 0.0509(10) Uani 1 1 d . . . H6 H 0.3579 -0.5595 0.9396 0.061 Uiso 1 1 calc R . . C7 C 0.4232(4) -0.2505(9) 0.8943(3) 0.0529(10) Uani 1 1 d . . . H7 H 0.4700 -0.2347 0.9551 0.063 Uiso 1 1 calc R . . C8 C 0.4229(3) -0.0788(9) 0.8153(3) 0.0512(10) Uani 1 1 d . . . H8 H 0.4694 0.0534 0.8221 0.061 Uiso 1 1 calc R . . C9 C 0.3547(4) -0.1011(8) 0.7271(3) 0.0490(9) Uani 1 1 d . . . H9 H 0.3539 0.0150 0.6725 0.059 Uiso 1 1 calc R . . N1 N 0.2220(3) -0.3284(6) 0.6249(2) 0.0474(8) Uani 1 1 d . . . N2 N 0.0993(3) -0.2774(7) 0.4983(3) 0.0509(9) Uani 1 1 d . . . H2 H 0.0439 -0.2184 0.4621 0.061 Uiso 1 1 calc R . . O1 O 0.3185(3) -0.6414(6) 0.5579(2) 0.0547(8) Uani 1 1 d . . . S1 S 0.08109(10) 0.0243(2) 0.66314(8) 0.0555(5) 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 C1 0.047(2) 0.061(3) 0.0426(17) 0.0101(17) -0.0075(15) -0.0007(18) C2 0.054(2) 0.053(2) 0.0383(17) 0.0008(15) -0.0003(16) 0.0043(17) C3 0.061(3) 0.058(3) 0.0354(16) -0.0004(16) -0.0036(16) 0.0012(19) C4 0.0470(19) 0.051(2) 0.0364(15) 0.0008(15) -0.0036(13) 0.0050(16) C5 0.063(3) 0.049(2) 0.0392(18) 0.0042(15) -0.0017(17) 0.0007(19) C6 0.060(2) 0.056(3) 0.0366(17) 0.0069(16) -0.0024(16) 0.0016(19) C7 0.058(2) 0.063(3) 0.0376(16) -0.0026(17) -0.0061(15) 0.005(2) C8 0.054(2) 0.056(2) 0.0440(19) -0.0014(18) -0.0042(16) -0.0005(18) C9 0.056(2) 0.053(2) 0.0379(17) 0.0043(16) -0.0033(15) 0.0036(19) N1 0.0510(18) 0.052(2) 0.0387(14) 0.0026(14) -0.0051(13) 0.0030(15) N2 0.0528(18) 0.059(2) 0.0406(15) -0.0011(14) -0.0095(13) 0.0061(16) O1 0.0633(19) 0.059(2) 0.0415(14) -0.0005(12) -0.0042(12) 0.0086(15) S1 0.0607(8) 0.0647(9) 0.0407(6) -0.0028(4) -0.0089(5) 0.0115(5) _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 C1 N2 1.331(5) . ? C1 N1 1.387(5) . ? C1 S1 1.666(5) . ? C2 O1 1.214(5) . ? C2 N1 1.391(5) . ? C2 C3 1.497(6) . ? C3 N2 1.447(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C9 1.380(6) . ? C4 C5 1.386(6) . ? C4 N1 1.434(5) . ? C5 C6 1.383(6) . ? C5 H5 0.9500 . ? C6 C7 1.373(7) . ? C6 H6 0.9500 . ? C7 C8 1.389(6) . ? C7 H7 0.9500 . ? C8 C9 1.380(5) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? N2 H2 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 107.3(4) . . ? N2 C1 S1 127.9(3) . . ? N1 C1 S1 124.7(3) . . ? O1 C2 N1 125.0(4) . . ? O1 C2 C3 128.7(4) . . ? N1 C2 C3 106.3(4) . . ? N2 C3 C2 102.0(3) . . ? N2 C3 H3A 111.4 . . ? C2 C3 H3A 111.4 . . ? N2 C3 H3B 111.4 . . ? C2 C3 H3B 111.4 . . ? H3A C3 H3B 109.2 . . ? C9 C4 C5 121.7(4) . . ? C9 C4 N1 119.6(3) . . ? C5 C4 N1 118.5(4) . . ? C6 C5 C4 118.6(4) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C7 C6 C5 120.2(4) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.7(4) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 119.8(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C4 C9 C8 119.0(4) . . ? C4 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C1 N1 C2 111.3(3) . . ? C1 N1 C4 126.7(4) . . ? C2 N1 C4 122.0(3) . . ? C1 N2 C3 113.2(3) . . ? C1 N2 H2 123.4 . . ? C3 N2 H2 123.4 . . ? 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 O1 C2 C3 N2 -178.9(5) . . . . ? N1 C2 C3 N2 -0.2(5) . . . . ? C9 C4 C5 C6 0.5(6) . . . . ? N1 C4 C5 C6 175.7(4) . . . . ? C4 C5 C6 C7 -0.1(7) . . . . ? C5 C6 C7 C8 -0.3(7) . . . . ? C6 C7 C8 C9 0.2(7) . . . . ? C5 C4 C9 C8 -0.6(7) . . . . ? N1 C4 C9 C8 -175.7(4) . . . . ? C7 C8 C9 C4 0.2(6) . . . . ? N2 C1 N1 C2 -0.7(5) . . . . ? S1 C1 N1 C2 178.6(3) . . . . ? N2 C1 N1 C4 176.8(4) . . . . ? S1 C1 N1 C4 -3.9(6) . . . . ? O1 C2 N1 C1 179.4(4) . . . . ? C3 C2 N1 C1 0.6(5) . . . . ? O1 C2 N1 C4 1.7(7) . . . . ? C3 C2 N1 C4 -177.0(4) . . . . ? C9 C4 N1 C1 -69.8(6) . . . . ? C5 C4 N1 C1 114.9(5) . . . . ? C9 C4 N1 C2 107.4(5) . . . . ? C5 C4 N1 C2 -67.9(5) . . . . ? N1 C1 N2 C3 0.6(5) . . . . ? S1 C1 N2 C3 -178.8(4) . . . . ? C2 C3 N2 C1 -0.2(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 S1 0.88 2.44 3.308(4) 168.1 3_556 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 34.75 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.763 _refine_diff_density_min -0.820 _refine_diff_density_rms 0.173 # Attachment '4 revised.cif' data_sja8_06m _database_code_depnum_ccdc_archive 'CCDC 756018' #TrackingRef '4 revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N2 O S' _chemical_formula_weight 282.35 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' 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' 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 C2/c 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' '-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 28.380(6) _cell_length_b 5.0073(6) _cell_length_c 20.811(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.952(16) _cell_angle_gamma 90.00 _cell_volume 2828.9(9) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 202 _cell_measurement_theta_min 8.55 _cell_measurement_theta_max 55.39 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS-II image plate' _diffrn_measurement_method '\w scans, 150 frames at 1\% intervals, exposure time 2 minutes' _diffrn_reflns_number 11195 _diffrn_reflns_av_R_equivalents 0.0839 _diffrn_reflns_av_sigmaI/netI 0.0805 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4096 _reflns_number_gt 1720 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'SHELXL97(Sheldrick, 1997) and WinGX (Farrugia, 1999)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.006(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4096 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1901 _refine_ls_R_factor_gt 0.1072 _refine_ls_wR_factor_ref 0.3591 _refine_ls_wR_factor_gt 0.3080 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 C1 C 0.20124(14) 1.0648(8) 0.0597(2) 0.0463(9) Uani 1 1 d . . . C2 C 0.21288(19) 0.7278(14) 0.1353(3) 0.088(2) Uani 1 1 d . . . C3 C 0.26194(18) 0.7598(11) 0.1212(3) 0.0648(12) Uani 1 1 d . . . H3 H 0.2694 0.6009 0.0968 0.078 Uiso 1 1 calc R . . C4 C 0.12857(15) 0.9334(9) 0.0987(2) 0.0539(10) Uani 1 1 d . . . C5 C 0.0958(2) 0.7611(15) 0.0617(5) 0.115(3) Uani 1 1 d . . . H5 H 0.1054 0.6329 0.0343 0.138 Uiso 1 1 calc R . . C6 C 0.0468(2) 0.7730(15) 0.0641(7) 0.145(4) Uani 1 1 d . . . H6 H 0.0230 0.6512 0.0385 0.174 Uiso 1 1 calc R . . C7 C 0.0341(3) 0.9532(17) 0.1020(5) 0.112(3) Uani 1 1 d . . . H7 H 0.0007 0.9648 0.1020 0.135 Uiso 1 1 calc R . . C8 C 0.0676(3) 1.122(2) 0.1408(4) 0.110(3) Uani 1 1 d . . . H8 H 0.0580 1.2463 0.1691 0.131 Uiso 1 1 calc R . . C9 C 0.1158(3) 1.1131(15) 0.1392(3) 0.0923(19) Uani 1 1 d . . . H9 H 0.1397 1.2314 0.1661 0.111 Uiso 1 1 calc R . . C10 C 0.30081(18) 0.8073(15) 0.1824(3) 0.0838(18) Uani 1 1 d . . . H10A H 0.3049 0.6440 0.2103 0.101 Uiso 1 1 calc R . . H10B H 0.2900 0.9518 0.2074 0.101 Uiso 1 1 calc R . . C11 C 0.35085(17) 0.8828(12) 0.1754(3) 0.0683(14) Uani 1 1 d . . . C12 C 0.37776(19) 1.0828(15) 0.2129(3) 0.0843(17) Uani 1 1 d . . . H12 H 0.3649 1.1805 0.2432 0.101 Uiso 1 1 calc R . . C13 C 0.4233(2) 1.1434(18) 0.2070(5) 0.110(3) Uani 1 1 d . . . H13 H 0.4413 1.2864 0.2329 0.132 Uiso 1 1 calc R . . C14 C 0.4433(2) 1.0097(19) 0.1666(5) 0.106(3) Uani 1 1 d . . . H14 H 0.4760 1.0483 0.1662 0.128 Uiso 1 1 calc R . . C15 C 0.4167(3) 0.816(2) 0.1256(5) 0.115(3) Uani 1 1 d . . . H15 H 0.4299 0.7307 0.0939 0.138 Uiso 1 1 calc R . . C16 C 0.3697(2) 0.7432(15) 0.1300(4) 0.093(2) Uani 1 1 d . . . H16 H 0.3514 0.6038 0.1029 0.111 Uiso 1 1 calc R . . N1 N 0.17967(12) 0.9151(8) 0.09942(18) 0.0551(9) Uani 1 1 d . . . N2 N 0.24879(13) 0.9932(9) 0.0762(2) 0.0611(11) Uani 1 1 d . . . H2 H 0.271(2) 1.056(11) 0.055(3) 0.073 Uiso 1 1 d . . . O1 O 0.20418(14) 0.5592(12) 0.1738(3) 0.118(2) Uani 1 1 d . . . S1 S 0.17297(5) 1.2763(3) 0.00174(8) 0.0782(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 C1 0.046(2) 0.049(2) 0.050(2) 0.0018(17) 0.0240(17) 0.0003(16) C2 0.047(3) 0.129(5) 0.080(3) 0.053(3) 0.006(2) -0.020(3) C3 0.057(3) 0.074(3) 0.066(3) 0.012(2) 0.023(2) -0.007(2) C4 0.048(2) 0.061(3) 0.060(2) 0.004(2) 0.0262(19) -0.0016(19) C5 0.048(3) 0.112(5) 0.196(8) -0.069(5) 0.051(4) -0.013(3) C6 0.049(3) 0.103(5) 0.292(14) -0.063(7) 0.065(5) -0.019(3) C7 0.071(4) 0.109(5) 0.186(9) 0.057(6) 0.082(5) 0.032(4) C8 0.103(6) 0.138(7) 0.107(5) 0.019(5) 0.059(5) 0.051(5) C9 0.090(4) 0.110(5) 0.076(4) -0.009(3) 0.023(3) 0.026(4) C10 0.048(3) 0.138(5) 0.072(3) 0.035(3) 0.026(2) 0.003(3) C11 0.042(2) 0.096(4) 0.072(3) 0.038(3) 0.024(2) 0.016(2) C12 0.049(3) 0.118(5) 0.087(4) 0.006(4) 0.020(3) -0.002(3) C13 0.052(3) 0.127(6) 0.146(7) 0.018(5) 0.023(4) -0.003(4) C14 0.038(3) 0.152(7) 0.134(6) 0.063(5) 0.034(3) 0.011(4) C15 0.064(4) 0.157(7) 0.144(7) 0.046(6) 0.060(4) 0.041(5) C16 0.064(3) 0.113(5) 0.113(5) 0.012(4) 0.043(3) 0.013(3) N1 0.0451(18) 0.069(2) 0.0521(19) 0.0162(17) 0.0149(16) -0.0094(16) N2 0.0380(17) 0.087(3) 0.059(2) 0.032(2) 0.0155(16) -0.0036(17) O1 0.057(2) 0.174(5) 0.116(3) 0.089(4) 0.013(2) -0.017(3) S1 0.0577(7) 0.0873(10) 0.1062(12) 0.0520(8) 0.0498(7) 0.0289(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.341(5) . ? C1 N1 1.384(5) . ? C1 S1 1.630(4) . ? C2 O1 1.237(6) . ? C2 N1 1.384(7) . ? C2 C3 1.512(7) . ? C3 C10 1.441(8) . ? C3 N2 1.477(6) . ? C3 H3 1.0000 . ? C4 C5 1.336(8) . ? C4 C9 1.353(8) . ? C4 N1 1.449(5) . ? C5 C6 1.407(8) . ? C5 H5 0.9500 . ? C6 C7 1.315(12) . ? C6 H6 0.9500 . ? C7 C8 1.350(12) . ? C7 H7 0.9500 . ? C8 C9 1.381(10) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.517(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.359(9) . ? C11 C16 1.401(9) . ? C12 C13 1.368(8) . ? C12 H12 0.9500 . ? C13 C14 1.326(12) . ? C13 H13 0.9500 . ? C14 C15 1.363(13) . ? C14 H14 0.9500 . ? C15 C16 1.414(9) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N2 H2 0.93(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 106.8(3) . . ? N2 C1 S1 127.2(3) . . ? N1 C1 S1 125.9(3) . . ? O1 C2 N1 125.4(5) . . ? O1 C2 C3 124.5(5) . . ? N1 C2 C3 110.1(4) . . ? C10 C3 N2 114.6(5) . . ? C10 C3 C2 110.9(5) . . ? N2 C3 C2 97.5(4) . . ? C10 C3 H3 111.0 . . ? N2 C3 H3 111.0 . . ? C2 C3 H3 111.0 . . ? C5 C4 C9 121.4(5) . . ? C5 C4 N1 119.5(4) . . ? C9 C4 N1 119.0(5) . . ? C4 C5 C6 118.8(6) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C7 C6 C5 119.8(7) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 121.4(6) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C7 C8 C9 119.6(7) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C4 C9 C8 119.0(7) . . ? C4 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C3 C10 C11 116.9(5) . . ? C3 C10 H10A 108.1 . . ? C11 C10 H10A 108.1 . . ? C3 C10 H10B 108.1 . . ? C11 C10 H10B 108.1 . . ? H10A C10 H10B 107.3 . . ? C12 C11 C16 119.6(5) . . ? C12 C11 C10 120.9(5) . . ? C16 C11 C10 119.5(6) . . ? C11 C12 C13 120.0(7) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 122.4(8) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C13 C14 C15 119.6(6) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 120.3(7) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C11 C16 C15 117.9(8) . . ? C11 C16 H16 121.1 . . ? C15 C16 H16 121.1 . . ? C1 N1 C2 109.8(4) . . ? C1 N1 C4 125.1(4) . . ? C2 N1 C4 124.8(4) . . ? C1 N2 C3 115.1(3) . . ? C1 N2 H2 125(3) . . ? C3 N2 H2 119(3) . . ? 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 O1 C2 C3 C10 -57.3(9) . . . . ? N1 C2 C3 C10 122.2(6) . . . . ? O1 C2 C3 N2 -177.4(7) . . . . ? N1 C2 C3 N2 2.2(6) . . . . ? C9 C4 C5 C6 1.6(13) . . . . ? N1 C4 C5 C6 176.9(8) . . . . ? C4 C5 C6 C7 0.5(16) . . . . ? C5 C6 C7 C8 -2.5(16) . . . . ? C6 C7 C8 C9 2.4(14) . . . . ? C5 C4 C9 C8 -1.7(11) . . . . ? N1 C4 C9 C8 -177.0(6) . . . . ? C7 C8 C9 C4 -0.3(11) . . . . ? N2 C3 C10 C11 -62.3(7) . . . . ? C2 C3 C10 C11 -171.5(5) . . . . ? C3 C10 C11 C12 136.4(6) . . . . ? C3 C10 C11 C16 -44.1(8) . . . . ? C16 C11 C12 C13 -1.2(9) . . . . ? C10 C11 C12 C13 178.4(6) . . . . ? C11 C12 C13 C14 -1.4(11) . . . . ? C12 C13 C14 C15 4.7(12) . . . . ? C13 C14 C15 C16 -5.2(11) . . . . ? C12 C11 C16 C15 0.6(9) . . . . ? C10 C11 C16 C15 -179.0(6) . . . . ? C14 C15 C16 C11 2.6(10) . . . . ? N2 C1 N1 C2 -6.8(6) . . . . ? S1 C1 N1 C2 170.5(4) . . . . ? N2 C1 N1 C4 178.8(4) . . . . ? S1 C1 N1 C4 -3.8(7) . . . . ? O1 C2 N1 C1 -177.8(7) . . . . ? C3 C2 N1 C1 2.6(7) . . . . ? O1 C2 N1 C4 -3.4(11) . . . . ? C3 C2 N1 C4 177.0(4) . . . . ? C5 C4 N1 C1 96.3(7) . . . . ? C9 C4 N1 C1 -88.3(7) . . . . ? C5 C4 N1 C2 -77.3(8) . . . . ? C9 C4 N1 C2 98.1(7) . . . . ? N1 C1 N2 C3 8.8(5) . . . . ? S1 C1 N2 C3 -168.5(4) . . . . ? C10 C3 N2 C1 -123.9(5) . . . . ? C2 C3 N2 C1 -6.8(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 S1 0.93(6) 2.39(6) 3.316(4) 178(5) 7_575 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.370 _refine_diff_density_min -0.644 _refine_diff_density_rms 0.091 # Attachment '5.cif' data_sja10_06 _database_code_depnum_ccdc_archive 'CCDC 756019' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C9 H14 N2 O S' _chemical_formula_sum 'C9 H14 N2 O S' _chemical_formula_weight 198.28 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' 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' 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 9.5863(11) _cell_length_b 9.2632(7) _cell_length_c 11.9253(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.960(9) _cell_angle_gamma 90.00 _cell_volume 1053.24(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 309 _cell_measurement_theta_min 7.78 _cell_measurement_theta_max 64.84 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS-II image plate' _diffrn_measurement_method '\w scans, 155 frames at 1\% intervals, exposure time 1 minute' _diffrn_reflns_number 12811 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 34.77 _reflns_number_total 4526 _reflns_number_gt 3342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'SHELXL97(Sheldrick, 1997) and WinGX (Farrugia, 1999)' _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^)+(0.0911P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.041(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4526 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1487 _refine_ls_wR_factor_gt 0.1373 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _refine_ls_shift/su_max 0.038 _refine_ls_shift/su_mean 0.004 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 C1 C 0.67551(11) -0.04611(12) 0.00151(9) 0.0246(2) Uani 1 1 d . . . C2 C 0.64248(13) -0.15165(13) -0.17211(10) 0.0276(2) Uani 1 1 d . . . C3 C 0.63538(12) -0.26971(12) -0.08481(9) 0.0271(2) Uani 1 1 d . . . H3 H 0.5399(18) -0.3094(19) -0.0908(15) 0.032 Uiso 1 1 d . . . C4 C 0.68172(13) 0.11365(14) -0.17006(11) 0.0310(2) Uani 1 1 d . . . H4A H 0.6433 0.1898 -0.1238 0.037 Uiso 1 1 calc R . . H4B H 0.6242 0.1117 -0.2440 0.037 Uiso 1 1 calc R . . C5 C 0.82934(16) 0.15216(16) -0.18817(13) 0.0388(3) Uani 1 1 d . . . H5 H 0.8422 0.2364 -0.2314 0.047 Uiso 1 1 calc R . . C6 C 0.94270(17) 0.08069(18) -0.15006(15) 0.0437(3) Uani 1 1 d . . . H6A H 0.9352 -0.0042 -0.1064 0.052 Uiso 1 1 calc R . . H6B H 1.0323 0.1139 -0.1661 0.052 Uiso 1 1 calc R . . C7 C 0.73892(15) -0.39385(14) -0.09944(11) 0.0320(2) Uani 1 1 d . . . H7 H 0.7171 -0.4329 -0.1775 0.038 Uiso 1 1 calc R . . C8 C 0.89040(16) -0.34311(17) -0.08808(16) 0.0443(3) Uani 1 1 d . . . H8A H 0.9010 -0.2651 -0.1421 0.066 Uiso 1 1 calc R . . H8B H 0.9517 -0.4238 -0.1035 0.066 Uiso 1 1 calc R . . H8C H 0.9162 -0.3077 -0.0113 0.066 Uiso 1 1 calc R . . C9 C 0.7166(2) -0.51565(15) -0.01738(14) 0.0441(3) Uani 1 1 d . . . H9A H 0.6181 -0.5457 -0.0270 0.066 Uiso 1 1 calc R . . H9B H 0.7410 -0.4819 0.0601 0.066 Uiso 1 1 calc R . . H9C H 0.7764 -0.5977 -0.0324 0.066 Uiso 1 1 calc R . . N1 N 0.66906(11) -0.02478(11) -0.11482(8) 0.02621(19) Uani 1 1 d . . . N2 N 0.66193(11) -0.18728(11) 0.01906(8) 0.02696(19) Uani 1 1 d . . . H2 H 0.6552(19) -0.225(2) 0.0813(16) 0.032 Uiso 1 1 d . . . O1 O 0.62834(12) -0.16440(11) -0.27427(8) 0.0368(2) Uani 1 1 d . . . S1 S 0.69663(3) 0.08394(3) 0.09715(3) 0.03076(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 C1 0.0250(4) 0.0273(5) 0.0211(4) -0.0025(4) 0.0013(3) 0.0023(3) C2 0.0314(5) 0.0300(5) 0.0214(5) -0.0017(4) 0.0022(4) 0.0016(4) C3 0.0321(5) 0.0272(5) 0.0221(5) -0.0022(4) 0.0032(4) -0.0003(4) C4 0.0340(6) 0.0300(5) 0.0282(5) 0.0053(4) -0.0009(4) 0.0026(4) C5 0.0395(6) 0.0406(7) 0.0361(7) 0.0133(5) 0.0034(5) -0.0029(5) C6 0.0343(6) 0.0522(9) 0.0447(8) 0.0110(6) 0.0043(6) -0.0019(5) C7 0.0422(6) 0.0270(5) 0.0273(5) -0.0034(4) 0.0063(5) 0.0040(4) C8 0.0390(7) 0.0410(7) 0.0544(9) -0.0003(6) 0.0126(6) 0.0086(5) C9 0.0609(9) 0.0278(6) 0.0457(8) 0.0041(5) 0.0152(7) 0.0078(6) N1 0.0302(4) 0.0267(4) 0.0214(4) 0.0004(3) 0.0017(3) 0.0010(3) N2 0.0345(5) 0.0271(4) 0.0195(4) -0.0006(3) 0.0041(3) 0.0013(3) O1 0.0512(6) 0.0388(5) 0.0201(4) -0.0027(3) 0.0021(4) 0.0022(4) S1 0.03699(17) 0.02856(15) 0.02585(16) -0.00601(10) -0.00095(11) 0.00322(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 C1 N2 1.3328(15) . ? C1 N1 1.3963(14) . ? C1 S1 1.6568(11) . ? C2 O1 1.2175(14) . ? C2 N1 1.3700(15) . ? C2 C3 1.5163(17) . ? C3 N2 1.4549(15) . ? C3 C7 1.5408(17) . ? C3 H3 0.982(17) . ? C4 N1 1.4524(15) . ? C4 C5 1.497(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.313(2) . ? C5 H5 0.9500 . ? C6 H6A 0.9500 . ? C6 H6B 0.9500 . ? C7 C8 1.519(2) . ? C7 C9 1.523(2) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N2 H2 0.830(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 107.45(9) . . ? N2 C1 S1 127.75(9) . . ? N1 C1 S1 124.80(9) . . ? O1 C2 N1 125.30(11) . . ? O1 C2 C3 127.51(11) . . ? N1 C2 C3 107.19(9) . . ? N2 C3 C2 100.94(9) . . ? N2 C3 C7 115.49(10) . . ? C2 C3 C7 112.65(9) . . ? N2 C3 H3 109.7(10) . . ? C2 C3 H3 109.2(10) . . ? C7 C3 H3 108.6(10) . . ? N1 C4 C5 113.62(10) . . ? N1 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? N1 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 126.23(13) . . ? C6 C5 H5 116.9 . . ? C4 C5 H5 116.9 . . ? C5 C6 H6A 120.0 . . ? C5 C6 H6B 120.0 . . ? H6A C6 H6B 120.0 . . ? C8 C7 C9 111.64(13) . . ? C8 C7 C3 112.34(11) . . ? C9 C7 C3 110.18(11) . . ? C8 C7 H7 107.5 . . ? C9 C7 H7 107.5 . . ? C3 C7 H7 107.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C2 N1 C1 111.15(10) . . ? C2 N1 C4 123.44(10) . . ? C1 N1 C4 125.34(10) . . ? C1 N2 C3 113.11(9) . . ? C1 N2 H2 125.1(13) . . ? C3 N2 H2 121.0(13) . . ? 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 O1 C2 C3 N2 179.30(12) . . . . ? N1 C2 C3 N2 -0.35(12) . . . . ? O1 C2 C3 C7 55.55(17) . . . . ? N1 C2 C3 C7 -124.10(11) . . . . ? N1 C4 C5 C6 -6.8(2) . . . . ? N2 C3 C7 C8 -54.66(15) . . . . ? C2 C3 C7 C8 60.60(15) . . . . ? N2 C3 C7 C9 70.50(15) . . . . ? C2 C3 C7 C9 -174.24(12) . . . . ? O1 C2 N1 C1 178.31(12) . . . . ? C3 C2 N1 C1 -2.03(13) . . . . ? O1 C2 N1 C4 1.05(19) . . . . ? C3 C2 N1 C4 -179.30(10) . . . . ? N2 C1 N1 C2 3.81(13) . . . . ? S1 C1 N1 C2 -176.29(9) . . . . ? N2 C1 N1 C4 -178.99(10) . . . . ? S1 C1 N1 C4 0.91(16) . . . . ? C5 C4 N1 C2 -93.10(15) . . . . ? C5 C4 N1 C1 90.03(15) . . . . ? N1 C1 N2 C3 -4.11(13) . . . . ? S1 C1 N2 C3 175.98(9) . . . . ? C2 C3 N2 C1 2.78(12) . . . . ? C7 C3 N2 C1 124.56(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.830(18) 2.042(19) 2.8688(14) 174.2(18) 4_556 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 34.77 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.580 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.077 # Attachment '6.cif' data_sja11_06 _database_code_depnum_ccdc_archive 'CCDC 756020' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H10 N2 O S' _chemical_formula_sum 'C10 H10 N2 O S' _chemical_formula_weight 206.26 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' 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' 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 C2/c 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' '-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 21.9470(19) _cell_length_b 8.5282(8) _cell_length_c 11.4242(9) _cell_angle_alpha 90.00 _cell_angle_beta 115.115(6) _cell_angle_gamma 90.00 _cell_volume 1936.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 455 _cell_measurement_theta_min 7.66 _cell_measurement_theta_max 67.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS-II image plate' _diffrn_measurement_method '\w scans, 135 frames at 1\% intervals, exposure time 1 minute' _diffrn_reflns_number 10104 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 34.78 _reflns_number_total 4002 _reflns_number_gt 3315 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'SHELXL97(Sheldrick, 1997) and WinGX (Farrugia, 1999)' _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^)+(0.0670P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.020(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4002 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.383 _refine_ls_restrained_S_all 1.383 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.005 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 C1 C 0.07535(5) 0.68227(11) 0.57133(9) 0.01921(16) Uani 1 1 d . . . C2 C 0.08683(6) 0.63752(11) 0.77682(10) 0.02364(19) Uani 1 1 d . . . C3 C 0.09266(7) 0.48201(12) 0.71897(11) 0.0276(2) Uani 1 1 d . . . H3A H 0.1371 0.4327 0.7690 0.033 Uiso 1 1 calc R . . H3B H 0.0567 0.4087 0.7142 0.033 Uiso 1 1 calc R . . C4 C 0.07106(5) 0.91730(11) 0.70406(10) 0.02122(17) Uani 1 1 d . . . H4A H 0.0568 0.9301 0.7750 0.025 Uiso 1 1 calc R . . H4B H 0.0349 0.9601 0.6243 0.025 Uiso 1 1 calc R . . C5 C 0.13456(5) 1.01132(10) 0.73593(10) 0.02010(17) Uani 1 1 d . . . C6 C 0.18719(6) 1.00535(13) 0.85951(11) 0.0266(2) Uani 1 1 d . . . H6 H 0.1839 0.9384 0.9231 0.032 Uiso 1 1 calc R . . C7 C 0.24452(6) 1.09697(15) 0.89029(12) 0.0315(2) Uani 1 1 d . . . H7 H 0.2803 1.0916 0.9744 0.038 Uiso 1 1 calc R . . C8 C 0.24941(6) 1.19609(14) 0.79836(13) 0.0305(2) Uani 1 1 d . . . H8 H 0.2882 1.2598 0.8198 0.037 Uiso 1 1 calc R . . C9 C 0.19740(6) 1.20173(13) 0.67497(13) 0.0291(2) Uani 1 1 d . . . H9 H 0.2009 1.2684 0.6115 0.035 Uiso 1 1 calc R . . C10 C 0.14000(5) 1.11000(12) 0.64377(10) 0.02464(19) Uani 1 1 d . . . H10 H 0.1045 1.1149 0.5593 0.030 Uiso 1 1 calc R . . N1 N 0.07887(4) 0.74967(10) 0.68537(8) 0.01955(15) Uani 1 1 d . . . N2 N 0.08476(5) 0.52852(10) 0.59133(9) 0.02364(17) Uani 1 1 d . . . H2 H 0.0860 0.4624 0.5333 0.028 Uiso 1 1 calc R . . O1 O 0.08803(6) 0.66288(10) 0.88280(9) 0.0346(2) Uani 1 1 d . . . S1 S 0.061663(15) 0.77939(3) 0.43695(2) 0.02713(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 C1 0.0201(3) 0.0205(4) 0.0181(4) -0.0014(3) 0.0091(3) -0.0016(3) C2 0.0327(4) 0.0207(4) 0.0207(4) -0.0007(3) 0.0144(4) -0.0032(3) C3 0.0454(6) 0.0185(4) 0.0227(4) -0.0005(3) 0.0182(4) -0.0014(4) C4 0.0228(4) 0.0190(4) 0.0253(4) -0.0007(3) 0.0136(3) 0.0014(3) C5 0.0229(4) 0.0175(3) 0.0225(4) -0.0013(3) 0.0122(3) 0.0014(3) C6 0.0283(4) 0.0277(4) 0.0240(4) 0.0007(3) 0.0113(4) 0.0003(4) C7 0.0255(4) 0.0342(5) 0.0299(5) -0.0035(4) 0.0070(4) -0.0015(4) C8 0.0249(4) 0.0276(5) 0.0406(6) -0.0048(4) 0.0154(4) -0.0041(4) C9 0.0327(5) 0.0239(4) 0.0351(6) 0.0009(4) 0.0187(5) -0.0041(4) C10 0.0284(4) 0.0219(4) 0.0242(4) 0.0009(3) 0.0117(4) -0.0017(3) N1 0.0234(3) 0.0184(3) 0.0190(3) -0.0003(3) 0.0110(3) -0.0008(2) N2 0.0337(4) 0.0194(3) 0.0203(4) -0.0018(3) 0.0139(3) -0.0011(3) O1 0.0623(6) 0.0251(4) 0.0240(4) -0.0016(3) 0.0258(4) -0.0035(4) S1 0.03945(17) 0.02391(14) 0.01925(13) 0.00238(8) 0.01364(11) 0.00218(9) _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 C1 N2 1.3319(13) . ? C1 N1 1.3958(12) . ? C1 S1 1.6557(10) . ? C2 O1 1.2192(13) . ? C2 N1 1.3717(13) . ? C2 C3 1.5113(15) . ? C3 N2 1.4488(14) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.4662(13) . ? C4 C5 1.5124(13) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.3920(14) . ? C5 C6 1.3949(15) . ? C6 C7 1.3935(16) . ? C6 H6 0.9500 . ? C7 C8 1.3873(19) . ? C7 H7 0.9500 . ? C8 C9 1.3880(18) . ? C8 H8 0.9500 . ? C9 C10 1.3946(15) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? N2 H2 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 107.59(8) . . ? N2 C1 S1 127.26(8) . . ? N1 C1 S1 125.15(7) . . ? O1 C2 N1 125.08(10) . . ? O1 C2 C3 128.30(10) . . ? N1 C2 C3 106.61(8) . . ? N2 C3 C2 101.75(8) . . ? N2 C3 H3A 111.4 . . ? C2 C3 H3A 111.4 . . ? N2 C3 H3B 111.4 . . ? C2 C3 H3B 111.4 . . ? H3A C3 H3B 109.3 . . ? N1 C4 C5 113.53(8) . . ? N1 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? N1 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C10 C5 C6 119.19(9) . . ? C10 C5 C4 120.30(9) . . ? C6 C5 C4 120.46(9) . . ? C7 C6 C5 120.40(10) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 120.15(11) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 119.70(10) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C8 C9 C10 120.29(10) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C5 C10 C9 120.26(10) . . ? C5 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C2 N1 C1 111.25(8) . . ? C2 N1 C4 123.63(8) . . ? C1 N1 C4 125.02(8) . . ? C1 N2 C3 112.69(8) . . ? C1 N2 H2 123.7 . . ? C3 N2 H2 123.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 N2 177.63(12) . . . . ? N1 C2 C3 N2 -1.68(12) . . . . ? N1 C4 C5 C10 106.52(11) . . . . ? N1 C4 C5 C6 -76.21(12) . . . . ? C10 C5 C6 C7 -0.04(16) . . . . ? C4 C5 C6 C7 -177.34(10) . . . . ? C5 C6 C7 C8 0.59(18) . . . . ? C6 C7 C8 C9 -1.02(18) . . . . ? C7 C8 C9 C10 0.92(18) . . . . ? C6 C5 C10 C9 -0.06(15) . . . . ? C4 C5 C10 C9 177.24(9) . . . . ? C8 C9 C10 C5 -0.38(17) . . . . ? O1 C2 N1 C1 -176.20(11) . . . . ? C3 C2 N1 C1 3.14(11) . . . . ? O1 C2 N1 C4 0.38(17) . . . . ? C3 C2 N1 C4 179.72(9) . . . . ? N2 C1 N1 C2 -3.41(11) . . . . ? S1 C1 N1 C2 176.44(8) . . . . ? N2 C1 N1 C4 -179.93(9) . . . . ? S1 C1 N1 C4 -0.08(13) . . . . ? C5 C4 N1 C2 102.00(11) . . . . ? C5 C4 N1 C1 -81.89(12) . . . . ? N1 C1 N2 C3 2.22(12) . . . . ? S1 C1 N2 C3 -177.62(8) . . . . ? C2 C3 N2 C1 -0.35(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.88 2.04 2.9137(12) 171.7 6_565 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.450 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.063 # Attachment '7.cif' data_sja12_06 _database_code_depnum_ccdc_archive 'CCDC 756021' #TrackingRef '7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H16 N2 O S' _chemical_formula_sum 'C17 H16 N2 O S' _chemical_formula_weight 296.38 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' 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' 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0344(11) _cell_length_b 17.331(3) _cell_length_c 9.5981(11) _cell_angle_alpha 90.00 _cell_angle_beta 101.028(10) _cell_angle_gamma 90.00 _cell_volume 1475.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 385 _cell_measurement_theta_min 6.45 _cell_measurement_theta_max 65.73 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS-II image plate' _diffrn_measurement_method '\w scans, 96 frames at 2\% intervals, exposure time 1.5 minutes' _diffrn_reflns_number 20656 _diffrn_reflns_av_R_equivalents 0.1200 _diffrn_reflns_av_sigmaI/netI 0.0846 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 34.78 _reflns_number_total 6254 _reflns_number_gt 3616 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997)' _computing_publication_material 'SHELXL97(Sheldrick, 1997) and WinGX (Farrugia, 1999)' _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^)+(0.1372P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.094(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6254 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1185 _refine_ls_R_factor_gt 0.0733 _refine_ls_wR_factor_ref 0.2366 _refine_ls_wR_factor_gt 0.1926 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.002 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 C1 C 0.27187(19) 0.16068(10) 0.64482(19) 0.0308(3) Uani 1 1 d . . . C2 C 0.45373(19) 0.25252(10) 0.70973(18) 0.0287(3) Uani 1 1 d . . . C3 C 0.3510(2) 0.28004(10) 0.57538(19) 0.0312(3) Uani 1 1 d . . . H3 H 0.2940 0.3262 0.5987 0.037 Uiso 1 1 calc R . . C4 C 0.4661(2) 0.13693(10) 0.86668(19) 0.0310(3) Uani 1 1 d . . . H4A H 0.3852 0.1069 0.8981 0.037 Uiso 1 1 calc R . . H4B H 0.5089 0.1726 0.9446 0.037 Uiso 1 1 calc R . . C5 C 0.58871(19) 0.08167(9) 0.84218(19) 0.0287(3) Uani 1 1 d . . . C6 C 0.6688(2) 0.04147(10) 0.9588(2) 0.0316(3) Uani 1 1 d . . . H6 H 0.6452 0.0493 1.0501 0.038 Uiso 1 1 calc R . . C7 C 0.7823(2) -0.00979(11) 0.9430(2) 0.0369(4) Uani 1 1 d . . . H7 H 0.8373 -0.0359 1.0235 0.044 Uiso 1 1 calc R . . C8 C 0.8157(2) -0.02300(12) 0.8094(2) 0.0407(4) Uani 1 1 d . . . H8 H 0.8927 -0.0584 0.7980 0.049 Uiso 1 1 calc R . . C9 C 0.7354(3) 0.01600(12) 0.6932(2) 0.0414(4) Uani 1 1 d . . . H9 H 0.7575 0.0070 0.6017 0.050 Uiso 1 1 calc R . . C10 C 0.6227(2) 0.06825(11) 0.7088(2) 0.0355(4) Uani 1 1 d . . . H10 H 0.5688 0.0948 0.6283 0.043 Uiso 1 1 calc R . . C11 C 0.4334(2) 0.30147(11) 0.4548(2) 0.0344(4) Uani 1 1 d . . . H11A H 0.3579 0.3105 0.3670 0.041 Uiso 1 1 calc R . . H11B H 0.4893 0.3503 0.4794 0.041 Uiso 1 1 calc R . . C12 C 0.5420(2) 0.24028(11) 0.4266(2) 0.0335(4) Uani 1 1 d . . . C13 C 0.6928(2) 0.24484(12) 0.4915(2) 0.0380(4) Uani 1 1 d . . . H13 H 0.7273 0.2880 0.5498 0.046 Uiso 1 1 calc R . . C14 C 0.7940(3) 0.18735(14) 0.4726(3) 0.0523(6) Uani 1 1 d . . . H14 H 0.8968 0.1911 0.5181 0.063 Uiso 1 1 calc R . . C15 C 0.7446(4) 0.12469(14) 0.3874(4) 0.0644(9) Uani 1 1 d . . . H15 H 0.8138 0.0856 0.3730 0.077 Uiso 1 1 calc R . . C16 C 0.5938(4) 0.11890(14) 0.3228(3) 0.0621(8) Uani 1 1 d . . . H16 H 0.5597 0.0754 0.2654 0.074 Uiso 1 1 calc R . . C17 C 0.4926(3) 0.17662(13) 0.3417(2) 0.0460(5) Uani 1 1 d . . . H17 H 0.3896 0.1726 0.2968 0.055 Uiso 1 1 calc R . . N1 N 0.39998(16) 0.18221(8) 0.74319(16) 0.0290(3) Uani 1 1 d . . . N2 N 0.24727(17) 0.21564(10) 0.54562(17) 0.0342(3) Uani 1 1 d . . . H2 H 0.1753 0.2130 0.4697 0.041 Uiso 1 1 calc R . . O1 O 0.56296(15) 0.28609(8) 0.77542(14) 0.0343(3) Uani 1 1 d . . . S1 S 0.17115(6) 0.08193(3) 0.65420(6) 0.04048(17) 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 C1 0.0287(7) 0.0347(8) 0.0294(8) -0.0026(6) 0.0063(6) 0.0011(6) C2 0.0289(7) 0.0312(7) 0.0257(7) -0.0005(6) 0.0043(5) 0.0018(6) C3 0.0317(8) 0.0327(8) 0.0281(8) 0.0011(6) 0.0032(6) 0.0034(6) C4 0.0327(8) 0.0332(8) 0.0274(8) 0.0030(6) 0.0066(6) 0.0036(6) C5 0.0284(7) 0.0289(7) 0.0289(8) 0.0012(6) 0.0058(6) -0.0015(5) C6 0.0334(8) 0.0316(7) 0.0295(8) 0.0025(6) 0.0051(6) -0.0010(6) C7 0.0331(8) 0.0362(9) 0.0403(10) 0.0077(7) 0.0045(7) 0.0041(7) C8 0.0403(10) 0.0380(9) 0.0465(11) 0.0038(8) 0.0150(8) 0.0092(7) C9 0.0473(11) 0.0418(10) 0.0382(10) 0.0023(8) 0.0162(8) 0.0090(8) C10 0.0405(9) 0.0361(8) 0.0309(9) 0.0040(7) 0.0090(7) 0.0054(7) C11 0.0376(9) 0.0348(8) 0.0303(8) 0.0053(6) 0.0050(6) 0.0033(7) C12 0.0394(9) 0.0331(8) 0.0297(8) 0.0028(6) 0.0107(7) -0.0016(7) C13 0.0373(9) 0.0389(9) 0.0406(10) 0.0057(7) 0.0141(7) -0.0012(7) C14 0.0464(11) 0.0517(12) 0.0666(16) 0.0214(11) 0.0303(11) 0.0115(10) C15 0.091(2) 0.0390(11) 0.083(2) 0.0130(12) 0.0649(18) 0.0146(12) C16 0.102(2) 0.0374(11) 0.0613(16) -0.0106(10) 0.0527(16) -0.0105(12) C17 0.0618(13) 0.0447(11) 0.0349(10) -0.0063(8) 0.0180(9) -0.0109(10) N1 0.0286(6) 0.0308(6) 0.0271(7) 0.0002(5) 0.0036(5) 0.0011(5) N2 0.0287(7) 0.0430(8) 0.0287(7) 0.0015(6) -0.0004(5) -0.0008(6) O1 0.0345(6) 0.0385(7) 0.0282(6) -0.0003(5) 0.0019(5) -0.0044(5) S1 0.0391(3) 0.0397(3) 0.0425(3) -0.00287(19) 0.0077(2) -0.00909(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 C1 N2 1.335(2) . ? C1 N1 1.397(2) . ? C1 S1 1.6523(19) . ? C2 O1 1.213(2) . ? C2 N1 1.372(2) . ? C2 C3 1.515(2) . ? C3 N2 1.450(2) . ? C3 C11 1.537(3) . ? C3 H3 1.0000 . ? C4 N1 1.451(2) . ? C4 C5 1.516(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.392(3) . ? C5 C6 1.397(2) . ? C6 C7 1.387(3) . ? C6 H6 0.9500 . ? C7 C8 1.391(3) . ? C7 H7 0.9500 . ? C8 C9 1.384(3) . ? C8 H8 0.9500 . ? C9 C10 1.392(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.504(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.388(3) . ? C12 C17 1.393(3) . ? C13 C14 1.387(3) . ? C13 H13 0.9500 . ? C14 C15 1.381(5) . ? C14 H14 0.9500 . ? C15 C16 1.388(5) . ? C15 H15 0.9500 . ? C16 C17 1.391(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? N2 H2 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 107.14(16) . . ? N2 C1 S1 127.58(15) . . ? N1 C1 S1 125.27(14) . . ? O1 C2 N1 126.39(16) . . ? O1 C2 C3 126.63(16) . . ? N1 C2 C3 106.98(14) . . ? N2 C3 C2 101.13(14) . . ? N2 C3 C11 115.18(15) . . ? C2 C3 C11 114.26(15) . . ? N2 C3 H3 108.6 . . ? C2 C3 H3 108.6 . . ? C11 C3 H3 108.6 . . ? N1 C4 C5 114.43(14) . . ? N1 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? N1 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C10 C5 C6 118.82(16) . . ? C10 C5 C4 122.99(16) . . ? C6 C5 C4 118.19(16) . . ? C7 C6 C5 120.79(18) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 120.12(18) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 119.29(18) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 120.83(19) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C5 C10 C9 120.15(18) . . ? C5 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C3 113.07(15) . . ? C12 C11 H11A 109.0 . . ? C3 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? C3 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C17 119.0(2) . . ? C13 C12 C11 119.81(18) . . ? C17 C12 C11 121.12(19) . . ? C14 C13 C12 121.0(2) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C13 119.7(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.0(2) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 120.2(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 120.1(3) . . ? C16 C17 H17 120.0 . . ? C12 C17 H17 120.0 . . ? C2 N1 C1 111.32(15) . . ? C2 N1 C4 124.22(15) . . ? C1 N1 C4 124.45(15) . . ? C1 N2 C3 113.30(15) . . ? C1 N2 H2 123.3 . . ? C3 N2 H2 123.3 . . ? 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 O1 C2 C3 N2 178.09(17) . . . . ? N1 C2 C3 N2 -1.84(17) . . . . ? O1 C2 C3 C11 53.7(2) . . . . ? N1 C2 C3 C11 -126.19(16) . . . . ? N1 C4 C5 C10 -7.6(2) . . . . ? N1 C4 C5 C6 173.73(15) . . . . ? C10 C5 C6 C7 1.3(3) . . . . ? C4 C5 C6 C7 -179.93(16) . . . . ? C5 C6 C7 C8 -1.4(3) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C7 C8 C9 C10 0.3(3) . . . . ? C6 C5 C10 C9 -0.5(3) . . . . ? C4 C5 C10 C9 -179.16(18) . . . . ? C8 C9 C10 C5 -0.3(3) . . . . ? N2 C3 C11 C12 -67.0(2) . . . . ? C2 C3 C11 C12 49.5(2) . . . . ? C3 C11 C12 C13 -94.0(2) . . . . ? C3 C11 C12 C17 82.7(2) . . . . ? C17 C12 C13 C14 0.2(3) . . . . ? C11 C12 C13 C14 176.99(18) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 -0.9(4) . . . . ? C14 C15 C16 C17 1.0(4) . . . . ? C15 C16 C17 C12 -0.5(4) . . . . ? C13 C12 C17 C16 -0.2(3) . . . . ? C11 C12 C17 C16 -176.87(19) . . . . ? O1 C2 N1 C1 179.86(17) . . . . ? C3 C2 N1 C1 -0.21(19) . . . . ? O1 C2 N1 C4 1.1(3) . . . . ? C3 C2 N1 C4 -178.99(15) . . . . ? N2 C1 N1 C2 2.4(2) . . . . ? S1 C1 N1 C2 -176.88(13) . . . . ? N2 C1 N1 C4 -178.82(15) . . . . ? S1 C1 N1 C4 1.9(3) . . . . ? C5 C4 N1 C2 -89.3(2) . . . . ? C5 C4 N1 C1 92.1(2) . . . . ? N1 C1 N2 C3 -3.8(2) . . . . ? S1 C1 N2 C3 175.49(14) . . . . ? C2 C3 N2 C1 3.49(19) . . . . ? C11 C3 N2 C1 127.21(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.88 1.95 2.801(2) 163.9 4_565 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 34.78 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.738 _refine_diff_density_min -0.821 _refine_diff_density_rms 0.120