data_mha91_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 N4 S' _chemical_formula_weight 208.29 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 ? _symmetry_space_group_name_H-M ? 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 8.7849(3) _cell_length_b 7.5662(3) _cell_length_c 15.4579(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.734(2) _cell_angle_gamma 90.00 _cell_volume 988.96(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8917 _exptl_absorpt_correction_T_max 0.9397 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13353 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 32.69 _reflns_number_total 3598 _reflns_number_gt 3052 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0354P)^2^+0.5044P] 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_number_reflns 3598 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.13201(3) 1.04175(4) 0.132350(18) 0.01294(7) Uani 1 1 d . . . N1 N 0.33066(11) 0.68401(14) 0.02551(6) 0.01473(19) Uani 1 1 d . . . N2 N 0.73382(11) 0.79609(13) 0.11663(6) 0.01196(17) Uani 1 1 d . . . N3 N 0.85425(11) 0.88006(13) 0.09177(6) 0.01252(18) Uani 1 1 d . . . N4 N 1.01031(11) 0.83201(13) 0.23519(6) 0.01234(18) Uani 1 1 d . . . C1 C 0.20882(13) 0.61524(17) 0.05103(8) 0.0174(2) Uani 1 1 d . . . H1A H 0.1074 0.6155 0.0090 0.021 Uiso 1 1 calc R . . C2 C 0.22280(14) 0.54390(16) 0.13530(8) 0.0163(2) Uani 1 1 d . . . H2A H 0.1335 0.4952 0.1503 0.020 Uiso 1 1 calc R . . C3 C 0.37053(14) 0.54519(16) 0.19751(8) 0.0155(2) Uani 1 1 d . . . H3A H 0.3841 0.4966 0.2558 0.019 Uiso 1 1 calc R . . C4 C 0.49802(13) 0.61849(15) 0.17333(7) 0.0133(2) Uani 1 1 d . . . H4A H 0.5998 0.6227 0.2149 0.016 Uiso 1 1 calc R . . C5 C 0.47313(12) 0.68608(14) 0.08616(7) 0.01105(19) Uani 1 1 d . . . C6 C 0.60294(12) 0.76932(14) 0.05527(7) 0.01100(19) Uani 1 1 d . . . C7 C 0.99346(12) 0.90965(15) 0.15598(7) 0.01093(19) Uani 1 1 d . . . C8 C 1.15311(13) 0.84674(16) 0.30947(7) 0.0144(2) Uani 1 1 d . . . H8A H 1.1462 0.7656 0.3577 0.022 Uiso 1 1 calc R . . H8B H 1.1638 0.9682 0.3323 0.022 Uiso 1 1 calc R . . H8C H 1.2454 0.8163 0.2884 0.022 Uiso 1 1 calc R . . C9 C 0.57533(13) 0.81858(16) -0.04166(7) 0.0146(2) Uani 1 1 d . . . H9A H 0.6067 0.9418 -0.0460 0.022 Uiso 1 1 calc R . . H9B H 0.4629 0.8046 -0.0728 0.022 Uiso 1 1 calc R . . H9C H 0.6383 0.7415 -0.0695 0.022 Uiso 1 1 calc R . . H1N4 H 0.9326(19) 0.771(2) 0.2425(11) 0.019(4) Uiso 1 1 d . . . H1N3 H 0.8473(19) 0.922(2) 0.0388(11) 0.021(4) 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 0.01165(12) 0.01653(14) 0.01071(12) -0.00074(9) 0.00315(9) -0.00436(9) N1 0.0116(4) 0.0185(5) 0.0132(4) 0.0001(4) 0.0020(3) -0.0031(3) N2 0.0105(4) 0.0124(4) 0.0133(4) 0.0004(3) 0.0036(3) -0.0019(3) N3 0.0103(4) 0.0169(5) 0.0097(4) 0.0014(3) 0.0016(3) -0.0037(3) N4 0.0107(4) 0.0151(4) 0.0105(4) 0.0006(3) 0.0015(3) -0.0028(3) C1 0.0116(5) 0.0228(6) 0.0175(5) -0.0001(4) 0.0033(4) -0.0048(4) C2 0.0157(5) 0.0156(5) 0.0201(5) -0.0005(4) 0.0090(4) -0.0029(4) C3 0.0189(5) 0.0143(5) 0.0149(5) 0.0017(4) 0.0074(4) -0.0001(4) C4 0.0139(5) 0.0131(5) 0.0125(5) 0.0012(4) 0.0030(4) 0.0003(4) C5 0.0112(4) 0.0104(4) 0.0117(4) -0.0002(4) 0.0033(3) -0.0008(4) C6 0.0115(4) 0.0108(5) 0.0108(4) 0.0001(4) 0.0033(3) 0.0002(4) C7 0.0107(4) 0.0113(4) 0.0106(4) -0.0018(4) 0.0027(3) -0.0006(4) C8 0.0132(4) 0.0171(5) 0.0109(4) 0.0007(4) -0.0002(4) -0.0007(4) C9 0.0129(4) 0.0198(5) 0.0112(5) 0.0005(4) 0.0033(4) -0.0029(4) _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 C7 1.6896(11) . ? N1 C1 1.3420(14) . ? N1 C5 1.3451(14) . ? N2 C6 1.2928(14) . ? N2 N3 1.3752(12) . ? N3 C7 1.3685(14) . ? N3 H1N3 0.865(17) . ? N4 C7 1.3297(14) . ? N4 C8 1.4572(14) . ? N4 H1N4 0.856(16) . ? C1 C2 1.3844(17) . ? C1 H1A 0.9500 . ? C2 C3 1.3901(17) . ? C2 H2A 0.9500 . ? C3 C4 1.3888(15) . ? C3 H3A 0.9500 . ? C4 C5 1.4019(15) . ? C4 H4A 0.9500 . ? C5 C6 1.4901(14) . ? C6 C9 1.4985(15) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 117.72(10) . . ? C6 N2 N3 117.77(9) . . ? C7 N3 N2 118.48(9) . . ? C7 N3 H1N3 116.5(11) . . ? N2 N3 H1N3 124.9(11) . . ? C7 N4 C8 123.29(9) . . ? C7 N4 H1N4 117.8(11) . . ? C8 N4 H1N4 118.9(11) . . ? N1 C1 C2 123.60(11) . . ? N1 C1 H1A 118.2 . . ? C2 C1 H1A 118.2 . . ? C1 C2 C3 118.44(10) . . ? C1 C2 H2A 120.8 . . ? C3 C2 H2A 120.8 . . ? C4 C3 C2 119.10(10) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 118.52(10) . . ? C3 C4 H4A 120.7 . . ? C5 C4 H4A 120.7 . . ? N1 C5 C4 122.60(10) . . ? N1 C5 C6 115.46(9) . . ? C4 C5 C6 121.92(10) . . ? N2 C6 C5 115.89(9) . . ? N2 C6 C9 124.42(10) . . ? C5 C6 C9 119.68(9) . . ? N4 C7 N3 116.74(9) . . ? N4 C7 S1 123.61(8) . . ? N3 C7 S1 119.64(8) . . ? N4 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N2 N3 C7 179.89(10) . . . . ? C5 N1 C1 C2 -1.27(19) . . . . ? N1 C1 C2 C3 0.82(19) . . . . ? C1 C2 C3 C4 0.38(18) . . . . ? C2 C3 C4 C5 -1.03(17) . . . . ? C1 N1 C5 C4 0.56(17) . . . . ? C1 N1 C5 C6 -178.03(10) . . . . ? C3 C4 C5 N1 0.58(17) . . . . ? C3 C4 C5 C6 179.08(10) . . . . ? N3 N2 C6 C5 -177.06(9) . . . . ? N3 N2 C6 C9 1.97(16) . . . . ? N1 C5 C6 N2 169.97(10) . . . . ? C4 C5 C6 N2 -8.63(16) . . . . ? N1 C5 C6 C9 -9.11(15) . . . . ? C4 C5 C6 C9 172.29(10) . . . . ? C8 N4 C7 N3 178.28(10) . . . . ? C8 N4 C7 S1 -2.50(16) . . . . ? N2 N3 C7 N4 9.52(15) . . . . ? N2 N3 C7 S1 -169.73(8) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 32.69 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.475 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.081