data_mao3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 N6 O2 S' _chemical_formula_sum 'C6 H4 N6 O2 S' _chemical_formula_weight 224.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.9024(9) _cell_length_b 12.0310(12) _cell_length_c 7.4151(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.371(2) _cell_angle_gamma 90.00 _cell_volume 877.95(13) _cell_formula_units_Z 4 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 1178 _cell_measurement_theta_min 2.674 _cell_measurement_theta_max 26.341 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.358 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.860042 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 108(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5254 _diffrn_reflns_av_R_equivalents 0.0604 _diffrn_reflns_av_sigmaI/netI 0.0727 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1548 _reflns_number_gt 1074 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEX _computing_cell_refinement APEX _computing_data_reduction APEX _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics XP _computing_publication_material CIFTAB _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^)+(0.0289P)^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 1548 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0704 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_restrained_S_all 0.896 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.65819(6) 0.52901(6) 0.21031(8) 0.01759(19) Uani 1 1 d . . . N1 N 0.79669(19) 0.59418(18) 0.3080(2) 0.0175(5) Uani 1 1 d . . . O1 O 0.70438(16) 0.42683(14) 0.1451(2) 0.0226(4) Uani 1 1 d . . . O2 O 0.55802(16) 0.53742(15) 0.3316(2) 0.0235(5) Uani 1 1 d . . . N2 N 0.7773(2) 0.69468(17) 0.3958(3) 0.0228(5) Uani 1 1 d . . . N3 N 0.8952(2) 0.73729(18) 0.4456(3) 0.0226(5) Uani 1 1 d . . . C3A C 0.9952(2) 0.6673(2) 0.3905(3) 0.0170(6) Uani 1 1 d . . . N4 N 0.6136(2) 0.60437(18) 0.0249(3) 0.0203(5) Uani 1 1 d . . . C4 C 1.1367(2) 0.6782(2) 0.4162(3) 0.0224(6) Uani 1 1 d . . . H4 H 1.1794 0.7401 0.4786 0.027 Uiso 1 1 calc R . . N5 N 0.5443(2) 0.6892(2) 0.0599(3) 0.0219(5) Uani 1 1 d . . . C5 C 1.2108(3) 0.5952(2) 0.3469(3) 0.0230(6) Uani 1 1 d . . . H5 H 1.3072 0.5999 0.3613 0.028 Uiso 1 1 calc R . . C6 C 1.1480(2) 0.5033(2) 0.2550(3) 0.0220(7) Uani 1 1 d . . . H6 H 1.2034 0.4482 0.2084 0.026 Uiso 1 1 calc R . . N6 N 0.4819(2) 0.7656(2) 0.0754(3) 0.0358(7) Uani 1 1 d . . . C7A C 0.9345(2) 0.5759(2) 0.3000(3) 0.0150(6) Uani 1 1 d . . . C7 C 1.0089(2) 0.4907(2) 0.2303(3) 0.0181(6) Uani 1 1 d . . . H7 H 0.9665 0.4282 0.1697 0.022 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0129(3) 0.0189(4) 0.0209(3) 0.0014(3) 0.0011(3) -0.0011(3) N1 0.0128(11) 0.0177(13) 0.0220(10) -0.0029(10) 0.0017(9) 0.0008(9) O1 0.0160(10) 0.0169(11) 0.0342(10) -0.0030(8) -0.0007(8) 0.0009(8) O2 0.0163(10) 0.0307(12) 0.0246(9) 0.0035(9) 0.0069(8) -0.0007(9) N2 0.0216(13) 0.0174(14) 0.0298(12) -0.0051(11) 0.0038(10) 0.0019(11) N3 0.0213(13) 0.0189(14) 0.0266(12) -0.0026(10) -0.0018(10) -0.0006(11) C3A 0.0161(14) 0.0187(16) 0.0154(12) 0.0021(12) -0.0023(11) -0.0022(12) N4 0.0174(12) 0.0217(14) 0.0222(11) 0.0019(10) 0.0036(9) 0.0030(10) C4 0.0226(15) 0.0203(17) 0.0230(14) 0.0023(12) -0.0032(12) -0.0071(13) N5 0.0163(13) 0.0259(15) 0.0227(12) 0.0054(11) -0.0010(10) -0.0028(12) C5 0.0125(14) 0.0303(18) 0.0259(13) 0.0054(13) 0.0000(12) -0.0040(13) C6 0.0185(15) 0.0289(18) 0.0195(13) 0.0029(12) 0.0057(12) 0.0049(12) N6 0.0326(15) 0.0305(17) 0.0449(15) 0.0088(13) 0.0061(12) 0.0118(13) C7A 0.0120(13) 0.0198(16) 0.0130(11) 0.0032(11) -0.0002(10) 0.0003(12) C7 0.0188(14) 0.0210(16) 0.0144(12) -0.0008(11) 0.0016(11) 0.0001(12) _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 O2 1.4147(16) . ? S1 O1 1.4152(18) . ? S1 N4 1.665(2) . ? S1 N1 1.673(2) . ? N1 C7A 1.390(3) . ? N1 N2 1.397(3) . ? N2 N3 1.291(3) . ? N3 C3A 1.394(3) . ? C3A C7A 1.390(3) . ? C3A C4 1.400(3) . ? N4 N5 1.273(3) . ? C4 C5 1.373(3) . ? C4 H4 0.9500 . ? N5 N6 1.121(3) . ? C5 C6 1.407(3) . ? C5 H5 0.9500 . ? C6 C7 1.378(3) . ? C6 H6 0.9500 . ? C7A C7 1.394(3) . ? C7 H7 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 123.73(11) . . ? O2 S1 N4 110.24(10) . . ? O1 S1 N4 104.90(10) . . ? O2 S1 N1 106.86(10) . . ? O1 S1 N1 105.92(10) . . ? N4 S1 N1 103.39(11) . . ? C7A N1 N2 110.08(19) . . ? C7A N1 S1 131.98(17) . . ? N2 N1 S1 117.31(16) . . ? N3 N2 N1 108.07(19) . . ? N2 N3 C3A 109.0(2) . . ? C7A C3A N3 109.7(2) . . ? C7A C3A C4 120.8(2) . . ? N3 C3A C4 129.5(2) . . ? N5 N4 S1 111.59(16) . . ? C5 C4 C3A 116.7(2) . . ? C5 C4 H4 121.6 . . ? C3A C4 H4 121.6 . . ? N6 N5 N4 174.2(3) . . ? C4 C5 C6 121.8(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 122.2(2) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C3A C7A N1 103.2(2) . . ? C3A C7A C7 122.9(2) . . ? N1 C7A C7 133.9(2) . . ? C6 C7 C7A 115.5(2) . . ? C6 C7 H7 122.2 . . ? C7A C7 H7 122.2 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.278 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.068