# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 440/118 data_mkf49 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H7 N O4 S Zn' _chemical_formula_weight 314.61 _chemical_melting_point ? _chemical_compound_source ? 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' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 7.853(1) _cell_length_b 15.937(1) _cell_length_c 9.993(1) _cell_angle_alpha 90.00 _cell_angle_beta 95.65(1) _cell_angle_gamma 90.00 _cell_volume 1244.6(1) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Prismatic crystal fragment' _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method ? _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 2.144 _exptl_absorpt_correction_type Sadabs _exptl_absorpt_correction_T_min 0.612 _exptl_absorpt_correction_T_max 0.928 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7058 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 26.34 _reflns_number_total 2517 _reflns_number_observed 2147 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+0.2807P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2517 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_obs 0.0250 _refine_ls_wR_factor_all 0.0677 _refine_ls_wR_factor_obs 0.0650 _refine_ls_goodness_of_fit_all 1.038 _refine_ls_goodness_of_fit_obs 1.085 _refine_ls_restrained_S_all 1.038 _refine_ls_restrained_S_obs 1.085 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn1 Zn 0.15306(3) 0.973921(13) 0.59506(2) 0.02976(9) Uani 1 d . . S1 S 0.19268(7) 1.25979(3) 0.24308(6) 0.03694(14) Uani 1 d . . O1 O 0.2024(2) 0.89755(10) 0.4368(2) 0.0468(4) Uani 1 d . . O2 O 0.0291(2) 1.06412(11) 0.6986(2) 0.0529(5) Uani 1 d . . O3 O -0.0218(2) 0.88687(10) 0.6417(2) 0.0473(4) Uani 1 d . . O4 O 0.2491(2) 1.07233(10) 0.4973(2) 0.0468(4) Uani 1 d . . N1 N 0.3495(2) 0.94774(12) 0.7373(2) 0.0362(4) Uani 1 d . . C2 C 0.3367(4) 0.8868(2) 0.8282(3) 0.0543(7) Uani 1 d . . H2B H 0.2359(4) 0.8559(2) 0.8251(3) 0.065 Uiso 1 calc R . C3 C 0.4670(5) 0.8683(2) 0.9259(3) 0.0689(9) Uani 1 d . . H3B H 0.4546(5) 0.8254(2) 0.9872(3) 0.083 Uiso 1 calc R . C4 C 0.6139(4) 0.9135(2) 0.9318(3) 0.0702(9) Uani 1 d . . H4A H 0.7026(4) 0.9025(2) 0.9982(3) 0.084 Uiso 1 calc R . C5 C 0.6305(4) 0.9753(2) 0.8397(3) 0.0616(8) Uani 1 d . . H5A H 0.7309(4) 1.0064(2) 0.8419(3) 0.074 Uiso 1 calc R . C6 C 0.4971(3) 0.9909(2) 0.7436(3) 0.0451(6) Uani 1 d . . H6A H 0.5093(3) 1.0329(2) 0.6806(3) 0.054 Uiso 1 calc R . C7 C 0.1727(3) 1.12026(13) 0.4111(2) 0.0353(5) Uani 1 d . . C8 C 0.2742(3) 1.19265(13) 0.3684(2) 0.0340(5) Uani 1 d . . C9 C 0.4368(3) 1.2137(2) 0.4167(2) 0.0482(6) Uani 1 d . . H9A H 0.5016(3) 1.1841(2) 0.4840(2) 0.058 Uiso 1 calc R . C10 C 0.4953(3) 1.2855(2) 0.3529(3) 0.0521(7) Uani 1 d . . H10A H 0.6035(3) 1.3085(2) 0.3739(3) 0.062 Uiso 1 calc R . C11 C 0.3777(3) 1.31778(13) 0.2573(2) 0.0368(5) Uani 1 d . . C12 C 0.4022(3) 1.38998(13) 0.1649(2) 0.0376(5) Uani 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 Zn1 0.03783(15) 0.01856(13) 0.03451(15) 0.00264(9) 0.01173(10) 0.00226(9) S1 0.0403(3) 0.0276(3) 0.0438(3) 0.0102(2) 0.0085(2) -0.0043(2) O1 0.0574(10) 0.0355(9) 0.0489(10) -0.0155(7) 0.0127(8) 0.0047(7) O2 0.0649(12) 0.0387(10) 0.0574(11) -0.0075(8) 0.0173(9) 0.0208(9) O3 0.0454(10) 0.0337(9) 0.0643(11) 0.0135(8) 0.0135(8) -0.0066(7) O4 0.0633(11) 0.0303(8) 0.0478(10) 0.0131(8) 0.0104(8) -0.0082(8) N1 0.0449(10) 0.0295(9) 0.0358(10) 0.0042(8) 0.0121(8) 0.0059(8) C2 0.071(2) 0.0438(15) 0.049(2) 0.0146(12) 0.0131(13) -0.0032(13) C3 0.094(2) 0.063(2) 0.050(2) 0.0263(14) 0.006(2) 0.013(2) C4 0.070(2) 0.086(2) 0.053(2) 0.008(2) -0.0040(15) 0.026(2) C5 0.049(2) 0.077(2) 0.059(2) 0.004(2) 0.0052(13) 0.0040(14) C6 0.0469(13) 0.0456(14) 0.0443(13) 0.0058(11) 0.0116(11) 0.0032(11) C7 0.0524(14) 0.0203(10) 0.0361(11) 0.0008(9) 0.0185(10) -0.0028(9) C8 0.0466(12) 0.0235(10) 0.0332(11) 0.0043(9) 0.0106(9) -0.0037(9) C9 0.060(2) 0.0378(13) 0.0451(14) 0.0125(11) -0.0040(11) -0.0115(11) C10 0.0532(15) 0.0412(14) 0.060(2) 0.0097(12) -0.0046(12) -0.0201(12) C11 0.0471(13) 0.0249(10) 0.0399(12) 0.0043(9) 0.0115(10) -0.0074(9) C12 0.0490(13) 0.0228(10) 0.0449(13) 0.0015(9) 0.0244(11) -0.0051(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 Zn1 O4 2.0321(15) . ? Zn1 N1 2.035(2) . ? Zn1 O3 2.038(2) . ? Zn1 O1 2.062(2) . ? Zn1 O2 2.069(2) . ? Zn1 Zn1 3.0300(5) 3_576 ? S1 C11 1.716(2) . ? S1 C8 1.722(2) . ? O1 C12 1.248(3) 2_545 ? O2 C12 1.255(3) 4_586 ? O3 C7 1.254(3) 3_576 ? O4 C7 1.259(3) . ? N1 C2 1.340(3) . ? N1 C6 1.344(3) . ? C2 C3 1.375(4) . ? C3 C4 1.357(5) . ? C4 C5 1.363(4) . ? C5 C6 1.373(4) . ? C7 O3 1.254(3) 3_576 ? C7 C8 1.488(3) . ? C8 C9 1.362(3) . ? C9 C10 1.409(3) . ? C10 C11 1.363(3) . ? C11 C12 1.500(3) . ? C12 O1 1.248(3) 2 ? C12 O2 1.255(3) 4_685 ? 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 O4 Zn1 N1 101.68(7) . . ? O4 Zn1 O3 157.80(7) . . ? N1 Zn1 O3 100.49(7) . . ? O4 Zn1 O1 88.87(7) . . ? N1 Zn1 O1 103.17(7) . . ? O3 Zn1 O1 87.43(7) . . ? O4 Zn1 O2 85.38(7) . . ? N1 Zn1 O2 98.91(7) . . ? O3 Zn1 O2 89.87(8) . . ? O1 Zn1 O2 157.88(7) . . ? O4 Zn1 Zn1 78.22(5) . 3_576 ? N1 Zn1 Zn1 173.81(5) . 3_576 ? O3 Zn1 Zn1 79.60(5) . 3_576 ? O1 Zn1 Zn1 83.02(5) . 3_576 ? O2 Zn1 Zn1 74.91(5) . 3_576 ? C11 S1 C8 91.33(11) . . ? C12 O1 Zn1 121.54(14) 2_545 . ? C12 O2 Zn1 132.1(2) 4_586 . ? C7 O3 Zn1 126.55(14) 3_576 . ? C7 O4 Zn1 128.5(2) . . ? C2 N1 C6 117.5(2) . . ? C2 N1 Zn1 121.3(2) . . ? C6 N1 Zn1 121.2(2) . . ? N1 C2 C3 122.4(3) . . ? C4 C3 C2 119.2(3) . . ? C3 C4 C5 119.4(3) . . ? C4 C5 C6 119.1(3) . . ? N1 C6 C5 122.4(2) . . ? O3 C7 O4 126.9(2) 3_576 . ? O3 C7 C8 117.4(2) 3_576 . ? O4 C7 C8 115.7(2) . . ? C9 C8 C7 126.8(2) . . ? C9 C8 S1 111.9(2) . . ? C7 C8 S1 121.3(2) . . ? C8 C9 C10 112.0(2) . . ? C11 C10 C9 113.3(2) . . ? C10 C11 C12 127.0(2) . . ? C10 C11 S1 111.4(2) . . ? C12 C11 S1 121.4(2) . . ? O1 C12 O2 127.1(2) 2 4_685 ? O1 C12 C11 117.5(2) 2 . ? O2 C12 C11 115.4(2) 4_685 . ? _refine_diff_density_max 0.557 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.065 data_cbl12 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 N2 O6.50 S Zn' _chemical_formula_weight 436.73 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' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting P(-1) _symmetry_space_group_name_H-M Triclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.595(3) _cell_length_b 9.491(3) _cell_length_c 12.748(6) _cell_angle_alpha 69.31(3) _cell_angle_beta 85.99(3) _cell_angle_gamma 67.59(2) _cell_volume 896.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 446 _exptl_absorpt_coefficient_mu 1.524 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4111 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.56 _reflns_number_total 3850 _reflns_number_gt 3044 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0517P)^2^+0.2425P] 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 3850 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0984 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.006 _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 Zn Zn 0.47708(4) 0.40345(4) 0.69919(3) 0.03572(13) Uani 1 1 d . . . S1 S 1.02446(10) -0.07988(9) 0.66933(7) 0.03901(19) Uani 1 1 d . . . N1 N 0.5957(3) 0.3788(3) 0.8498(2) 0.0450(7) Uani 1 1 d . . . N2 N 0.3590(4) 0.2771(3) 0.8269(2) 0.0431(6) Uani 1 1 d . . . O1 O 0.7057(3) 0.3624(2) 0.62574(17) 0.0431(5) Uani 1 1 d . . . O2 O 0.6902(3) 0.1240(3) 0.7157(2) 0.0557(6) Uani 1 1 d . . . O3 O 0.3174(3) 0.6373(2) 0.66243(18) 0.0447(5) Uani 1 1 d . . . O4 O 1.4782(3) -0.2288(3) 0.5691(2) 0.0555(6) Uani 1 1 d . . . O5 O 0.3531(3) 0.3866(3) 0.57188(19) 0.0402(5) Uani 1 1 d . . . H5A H 0.316(4) 0.470(4) 0.528(3) 0.031(9) Uiso 1 1 d . . . H5B H 0.415(6) 0.322(6) 0.541(4) 0.087(16) Uiso 1 1 d . . . O6 O 0.3468(5) 0.1638(5) 0.2806(3) 0.0823(10) Uani 1 1 d . . . H6A H 0.394(8) 0.060(8) 0.299(5) 0.12(3) Uiso 1 1 d . . . H6B H 0.405(8) 0.162(7) 0.343(5) 0.12(2) Uiso 1 1 d . . . C1 C 0.7675(4) 0.2081(4) 0.6594(2) 0.0392(7) Uani 1 1 d . . . C2 C 0.9421(4) 0.1277(3) 0.6306(2) 0.0338(6) Uani 1 1 d . . . C3 C 1.0542(4) 0.1937(4) 0.5753(3) 0.0410(7) Uani 1 1 d . . . H3A H 1.0327 0.3081 0.5476 0.080 Uiso 1 1 d R . . C4 C 1.2075(4) 0.0745(4) 0.5659(3) 0.0439(8) Uani 1 1 d . . . H4A H 1.3003 0.0987 0.5289 0.080 Uiso 1 1 d R . . C5 C 1.2108(4) -0.0795(3) 0.6119(2) 0.0332(6) Uani 1 1 d . . . C6 C 1.3472(4) -0.2358(4) 0.6141(2) 0.0370(7) Uani 1 1 d . . . C7 C 0.7158(5) 0.4331(5) 0.8528(3) 0.0584(10) Uani 1 1 d . . . H7A H 0.7546 0.4861 0.7833 0.080 Uiso 1 1 d R . . C8 C 0.7867(5) 0.4150(6) 0.9549(4) 0.0713(12) Uani 1 1 d . . . H8A H 0.8712 0.4578 0.9556 0.080 Uiso 1 1 d R . . C9 C 0.7280(6) 0.3387(5) 1.0527(3) 0.0751(14) Uani 1 1 d . . . H9A H 0.7774 0.3231 1.1232 0.080 Uiso 1 1 d R . . C10 C 0.6041(6) 0.2820(5) 1.0496(3) 0.0614(11) Uani 1 1 d . . . H10A H 0.5623 0.2298 1.1180 0.080 Uiso 1 1 d R . . C11 C 0.5390(5) 0.3037(4) 0.9463(2) 0.0476(9) Uani 1 1 d . . . C12 C 0.4070(4) 0.2472(4) 0.9332(3) 0.0455(8) Uani 1 1 d . . . C13 C 0.3347(6) 0.1649(5) 1.0236(3) 0.0655(11) Uani 1 1 d . . . H13A H 0.3698 0.1472 1.0986 0.080 Uiso 1 1 d R . . C14 C 0.2171(6) 0.1122(5) 1.0040(4) 0.0732(12) Uani 1 1 d . . . H14A H 0.1675 0.0566 1.0664 0.080 Uiso 1 1 d R . . C15 C 0.1690(6) 0.1401(5) 0.8957(4) 0.0678(11) Uani 1 1 d . . . H15A H 0.0876 0.1029 0.8789 0.080 Uiso 1 1 d R . . C16 C 0.2428(5) 0.2236(4) 0.8102(3) 0.0544(9) Uani 1 1 d . . . H16A H 0.2109 0.2443 0.7338 0.080 Uiso 1 1 d R . . O7 O 0.0047(12) 0.4280(10) 0.2450(12) 0.131(6) Uani 0.50 1 d P . . H7BA H 0.027(11) 0.400(10) 0.197(6) 0.02(2) Uiso 0.50 1 d P . . H7BB H 0.017(9) 0.433(8) 0.312(4) 0.005(14) Uiso 0.50 1 d P . . 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 Zn 0.0372(2) 0.03043(18) 0.03010(18) -0.01206(13) 0.00593(13) -0.00241(14) S1 0.0324(4) 0.0274(3) 0.0460(4) -0.0113(3) 0.0064(3) -0.0019(3) N1 0.0408(15) 0.0483(15) 0.0365(14) -0.0204(12) 0.0016(11) -0.0019(12) N2 0.0536(17) 0.0344(13) 0.0315(13) -0.0118(11) 0.0087(11) -0.0073(12) O1 0.0435(12) 0.0287(10) 0.0366(11) -0.0101(8) 0.0052(9) 0.0059(9) O2 0.0471(14) 0.0430(13) 0.0635(15) -0.0171(11) 0.0172(12) -0.0069(11) O3 0.0417(12) 0.0283(11) 0.0536(13) -0.0166(10) 0.0035(10) -0.0005(9) O4 0.0433(14) 0.0549(14) 0.0788(17) -0.0453(13) 0.0234(12) -0.0129(11) O5 0.0453(13) 0.0341(12) 0.0331(11) -0.0142(10) 0.0060(10) -0.0050(10) O6 0.115(3) 0.090(3) 0.0587(19) -0.0208(18) 0.0027(18) -0.061(2) C1 0.0379(17) 0.0345(15) 0.0312(14) -0.0139(12) 0.0007(12) 0.0031(13) C2 0.0367(16) 0.0248(13) 0.0290(13) -0.0103(11) 0.0012(11) 0.0005(11) C3 0.0460(18) 0.0270(14) 0.0456(17) -0.0154(12) 0.0065(14) -0.0076(13) C4 0.0430(18) 0.0372(16) 0.0511(18) -0.0219(14) 0.0135(15) -0.0108(14) C5 0.0307(15) 0.0323(14) 0.0324(14) -0.0154(11) 0.0020(11) -0.0040(12) C6 0.0362(17) 0.0352(16) 0.0386(15) -0.0229(13) 0.0012(13) -0.0031(13) C7 0.047(2) 0.072(3) 0.060(2) -0.038(2) 0.0080(17) -0.0137(19) C8 0.050(2) 0.080(3) 0.084(3) -0.049(3) -0.008(2) -0.004(2) C9 0.079(3) 0.067(3) 0.052(2) -0.029(2) -0.022(2) 0.013(2) C10 0.073(3) 0.052(2) 0.0409(19) -0.0164(16) -0.0084(18) -0.0022(19) C11 0.056(2) 0.0359(16) 0.0310(15) -0.0139(13) -0.0002(14) 0.0062(15) C12 0.053(2) 0.0306(15) 0.0345(15) -0.0113(12) 0.0071(14) 0.0024(14) C13 0.082(3) 0.055(2) 0.0367(18) -0.0088(16) 0.0145(18) -0.011(2) C14 0.079(3) 0.056(2) 0.065(3) -0.007(2) 0.026(2) -0.023(2) C15 0.072(3) 0.053(2) 0.070(3) -0.013(2) 0.028(2) -0.027(2) C16 0.063(2) 0.049(2) 0.0482(19) -0.0185(16) 0.0110(17) -0.0182(18) O7 0.078(6) 0.048(5) 0.229(18) -0.016(9) 0.035(10) -0.020(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 Zn O3 2.015(2) . ? Zn O1 2.075(2) . ? Zn O5 2.086(2) . ? Zn N2 2.106(3) . ? Zn N1 2.135(3) . ? S1 C2 1.710(3) . ? S1 C5 1.714(3) . ? N1 C7 1.326(5) . ? N1 C11 1.349(4) . ? N2 C16 1.339(5) . ? N2 C12 1.344(4) . ? O1 C1 1.267(4) . ? O2 C1 1.235(4) . ? O3 C6 1.258(4) 1_465 ? O4 C6 1.241(4) . ? C1 C2 1.489(4) . ? C2 C3 1.368(4) . ? C3 C4 1.403(4) . ? C4 C5 1.358(4) . ? C5 C6 1.492(4) . ? C6 O3 1.258(4) 1_645 ? C7 C8 1.402(5) . ? C8 C9 1.373(7) . ? C9 C10 1.372(7) . ? C10 C11 1.384(5) . ? C11 C12 1.468(5) . ? C12 C13 1.399(5) . ? C13 C14 1.357(6) . ? C14 C15 1.373(6) . ? C15 C16 1.377(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn O1 117.01(9) . . ? O3 Zn O5 90.08(10) . . ? O1 Zn O5 94.64(9) . . ? O3 Zn N2 102.40(10) . . ? O1 Zn N2 139.77(9) . . ? O5 Zn N2 92.98(11) . . ? O3 Zn N1 96.76(10) . . ? O1 Zn N1 90.26(10) . . ? O5 Zn N1 168.70(10) . . ? N2 Zn N1 76.79(12) . . ? C2 S1 C5 91.79(14) . . ? C7 N1 C11 120.2(3) . . ? C7 N1 Zn 124.4(2) . . ? C11 N1 Zn 115.4(2) . . ? C16 N2 C12 118.2(3) . . ? C16 N2 Zn 125.3(2) . . ? C12 N2 Zn 116.5(2) . . ? C1 O1 Zn 100.7(2) . . ? C6 O3 Zn 128.1(2) 1_465 . ? O2 C1 O1 122.8(3) . . ? O2 C1 C2 119.8(3) . . ? O1 C1 C2 117.5(3) . . ? C3 C2 C1 130.2(3) . . ? C3 C2 S1 111.5(2) . . ? C1 C2 S1 118.3(2) . . ? C2 C3 C4 112.2(3) . . ? C5 C4 C3 113.4(3) . . ? C4 C5 C6 129.0(3) . . ? C4 C5 S1 111.1(2) . . ? C6 C5 S1 119.9(2) . . ? O4 C6 O3 126.4(3) . 1_645 ? O4 C6 C5 117.5(3) . . ? O3 C6 C5 116.1(3) 1_645 . ? N1 C7 C8 121.5(4) . . ? C9 C8 C7 118.0(4) . . ? C10 C9 C8 120.5(4) . . ? C9 C10 C11 118.8(4) . . ? N1 C11 C10 121.0(4) . . ? N1 C11 C12 115.6(3) . . ? C10 C11 C12 123.4(3) . . ? N2 C12 C13 120.5(4) . . ? N2 C12 C11 115.7(3) . . ? C13 C12 C11 123.7(3) . . ? C14 C13 C12 119.8(4) . . ? C13 C14 C15 120.1(4) . . ? C14 C15 C16 117.5(4) . . ? N2 C16 C15 123.8(4) . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.710 _refine_diff_density_min -0.514 _refine_diff_density_rms 0.070 data_mok10 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H12 N2 O5 S Zn' _chemical_formula_weight 433.73 _chemical_melting_point ? _chemical_compound_source ? 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' 'Zn' 'Zn' 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.977(2) _cell_length_b 15.558(2) _cell_length_c 11.376(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.36(3) _cell_angle_gamma 90.00 _cell_volume 1740.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method ? _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 1.564 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5289 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 24.93 _reflns_number_total 2990 _reflns_number_observed 2770 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+1.2671P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0213(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2990 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0262 _refine_ls_R_factor_obs 0.0235 _refine_ls_wR_factor_all 0.0671 _refine_ls_wR_factor_obs 0.0646 _refine_ls_goodness_of_fit_all 0.932 _refine_ls_goodness_of_fit_obs 0.936 _refine_ls_restrained_S_all 0.932 _refine_ls_restrained_S_obs 0.936 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn1 Zn 0.40613(2) 0.014327(14) 0.19840(2) 0.02422(11) Uani 1 d . . S1 S 0.71318(5) -0.22383(3) 0.24632(5) 0.02764(14) Uani 1 d . . O1 O 0.53720(14) -0.08174(9) 0.23468(13) 0.0306(3) Uani 1 d . . O2 O 0.5882(2) -0.07266(10) 0.44535(15) 0.0405(4) Uani 1 d . . O3 O 0.50740(14) 0.09868(9) 0.13247(14) 0.0337(3) Uani 1 d . . O4 O 0.8639(2) -0.34538(11) 0.17015(14) 0.0410(4) Uani 1 d . . O5 O 0.4023(2) 0.10830(10) 0.3219(2) 0.0339(3) Uani 1 d . . N1 N 0.2580(2) -0.05973(11) 0.2336(2) 0.0289(4) Uani 1 d . . C2 C 0.2612(2) -0.08424(15) 0.3466(2) 0.0371(5) Uani 1 d . . H2 H 0.3322(2) -0.06517(15) 0.4243(2) 0.045 Uiso 1 calc R . C3 C 0.1623(2) -0.1376(2) 0.3533(2) 0.0444(6) Uani 1 d . . H3 H 0.1678(2) -0.1538(2) 0.4342(2) 0.053 Uiso 1 calc R . C4 C 0.0579(2) -0.1654(2) 0.2403(3) 0.0451(6) Uani 1 d . . H4 H -0.0089(2) -0.2006(2) 0.2437(3) 0.054 Uiso 1 calc R . C5 C -0.0561(2) -0.1665(2) -0.0055(3) 0.0463(6) Uani 1 d . . H5 H -0.1258(2) -0.2015(2) -0.0077(3) 0.056 Uiso 1 calc R . C6 C -0.0574(2) -0.1409(2) -0.1184(3) 0.0470(6) Uani 1 d . . H6 H -0.1282(2) -0.1583(2) -0.1974(3) 0.056 Uiso 1 calc R . C7 C 0.0538(2) -0.0595(2) -0.2348(2) 0.0448(6) Uani 1 d . . H7 H -0.0138(2) -0.0757(2) -0.3164(2) 0.054 Uiso 1 calc R . C8 C 0.1586(3) -0.0085(2) -0.2265(2) 0.0439(6) Uani 1 d . . H8 H 0.1632(3) 0.0098(2) -0.3023(2) 0.053 Uiso 1 calc R . C9 C 0.2592(2) 0.01588(13) -0.1030(2) 0.0332(5) Uani 1 d . . H9 H 0.3304(2) 0.05051(13) -0.0981(2) 0.040 Uiso 1 calc R . N10 N 0.2562(2) -0.00875(10) 0.0068(2) 0.0267(3) Uani 1 d . . C11 C 0.0505(2) -0.14112(14) 0.1185(2) 0.0358(5) Uani 1 d . . C12 C 0.1539(2) -0.08733(12) 0.1202(2) 0.0278(4) Uani 1 d . . C13 C 0.1527(2) -0.05984(12) -0.0004(2) 0.0280(4) Uani 1 d . . C14 C 0.0482(2) -0.08710(14) -0.1203(2) 0.0361(5) Uani 1 d . . C15 C 0.5990(2) -0.10670(12) 0.3520(2) 0.0253(4) Uani 1 d . . C16 C 0.6927(2) -0.18102(12) 0.3754(2) 0.0253(4) Uani 1 d . . C17 C 0.7732(2) -0.22151(13) 0.4903(2) 0.0314(4) Uani 1 d . . H17 H 0.7749(2) -0.20739(13) 0.5704(2) 0.038 Uiso 1 calc R . C18 C 0.8538(2) -0.28700(13) 0.4749(2) 0.0303(4) Uani 1 d . . H18 H 0.9143(2) -0.32068(13) 0.5436(2) 0.036 Uiso 1 calc R . C19 C 0.8332(2) -0.29541(12) 0.3482(2) 0.0247(4) Uani 1 d . . C20 C 0.9004(2) -0.35246(12) 0.2904(2) 0.0276(4) Uani 1 d . . H5A H 0.4750(30) 0.1275(18) 0.3430(26) 0.046(8) Uiso 1 d . . H5B H 0.3995(29) 0.0941(20) 0.3940(32) 0.062(9) Uiso 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 Zn1 0.02139(14) 0.0220(2) 0.0292(2) -0.00147(8) 0.01115(10) -0.00152(8) S1 0.0305(3) 0.0299(3) 0.0239(2) 0.0038(2) 0.0134(2) 0.0094(2) O1 0.0330(7) 0.0311(7) 0.0303(8) 0.0033(6) 0.0163(6) 0.0097(6) O2 0.0542(9) 0.0388(8) 0.0358(8) -0.0033(7) 0.0265(7) 0.0113(7) O3 0.0353(8) 0.0320(7) 0.0369(8) -0.0061(6) 0.0188(7) -0.0126(6) O4 0.0397(8) 0.0512(10) 0.0310(8) 0.0006(7) 0.0148(7) 0.0163(7) O5 0.0372(9) 0.0329(8) 0.0356(8) -0.0048(7) 0.0196(7) -0.0039(7) N1 0.0252(8) 0.0292(9) 0.0319(9) -0.0019(7) 0.0123(7) -0.0044(7) C2 0.0347(11) 0.0435(12) 0.0345(11) 0.0027(9) 0.0166(9) -0.0011(9) C3 0.0475(13) 0.0460(13) 0.0479(14) 0.0079(11) 0.0286(12) -0.0040(11) C4 0.0397(12) 0.0399(13) 0.065(2) 0.0029(12) 0.0319(12) -0.0105(10) C5 0.0318(12) 0.0460(13) 0.060(2) -0.0113(12) 0.0194(11) -0.0160(10) C6 0.0278(11) 0.0521(14) 0.0493(14) -0.0154(12) 0.0064(10) -0.0095(10) C7 0.0384(12) 0.0510(14) 0.0318(11) -0.0069(10) 0.0035(10) 0.0030(11) C8 0.0516(14) 0.0472(13) 0.0309(12) 0.0037(10) 0.0164(11) 0.0065(11) C9 0.0340(11) 0.0308(11) 0.0353(11) 0.0042(9) 0.0159(9) 0.0029(8) N10 0.0242(8) 0.0245(8) 0.0310(9) 0.0003(7) 0.0119(7) 0.0008(6) C11 0.0281(10) 0.0308(11) 0.0496(13) -0.0046(9) 0.0184(9) -0.0057(8) C12 0.0228(9) 0.0229(9) 0.0382(11) -0.0020(8) 0.0141(8) 0.0000(7) C13 0.0229(9) 0.0236(9) 0.0352(11) -0.0029(8) 0.0108(8) 0.0012(7) C14 0.0273(10) 0.0378(12) 0.0360(11) -0.0073(9) 0.0075(9) 0.0000(9) C15 0.0250(9) 0.0240(9) 0.0306(10) -0.0011(8) 0.0156(8) -0.0016(7) C16 0.0281(9) 0.0238(9) 0.0263(9) -0.0016(7) 0.0141(8) 0.0000(8) C17 0.0356(11) 0.0330(11) 0.0244(10) -0.0017(8) 0.0122(9) 0.0020(8) C18 0.0293(10) 0.0283(10) 0.0287(10) 0.0057(8) 0.0088(8) 0.0047(8) C19 0.0216(9) 0.0218(9) 0.0299(10) 0.0028(7) 0.0107(8) 0.0015(7) C20 0.0253(9) 0.0229(9) 0.0366(11) 0.0004(8) 0.0154(8) 0.0005(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.9866(13) . ? Zn1 O5 2.0413(15) . ? Zn1 O3 2.0641(14) . ? Zn1 N10 2.098(2) . ? Zn1 N1 2.171(2) . ? S1 C16 1.715(2) . ? S1 C19 1.721(2) . ? O1 C15 1.261(2) . ? O2 C15 1.239(2) . ? O3 C20 1.258(2) 4_766 ? O4 C20 1.248(2) . ? N1 C2 1.325(3) . ? N1 C12 1.358(3) . ? C2 C3 1.395(3) . ? C3 C4 1.358(4) . ? C4 C11 1.404(3) . ? C5 C6 1.339(4) . ? C5 C11 1.431(3) . ? C6 C14 1.437(3) . ? C7 C8 1.366(4) . ? C7 C14 1.399(3) . ? C8 C9 1.400(3) . ? C9 N10 1.321(3) . ? N10 C13 1.359(3) . ? C11 C12 1.403(3) . ? C12 C13 1.432(3) . ? C13 C14 1.402(3) . ? C15 C16 1.491(3) . ? C16 C17 1.364(3) . ? C17 C18 1.410(3) . ? C18 C19 1.362(3) . ? C19 C20 1.482(3) . ? C20 O3 1.258(2) 4_756 ? 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 O1 Zn1 O5 129.07(6) . . ? O1 Zn1 O3 95.55(6) . . ? O5 Zn1 O3 88.50(6) . . ? O1 Zn1 N10 104.40(6) . . ? O5 Zn1 N10 126.25(6) . . ? O3 Zn1 N10 91.82(6) . . ? O1 Zn1 N1 95.46(6) . . ? O5 Zn1 N1 90.40(7) . . ? O3 Zn1 N1 166.66(6) . . ? N10 Zn1 N1 78.15(6) . . ? C16 S1 C19 91.53(9) . . ? C15 O1 Zn1 116.84(12) . . ? C20 O3 Zn1 121.80(13) 4_766 . ? C2 N1 C12 118.6(2) . . ? C2 N1 Zn1 129.17(14) . . ? C12 N1 Zn1 112.06(13) . . ? N1 C2 C3 122.5(2) . . ? C4 C3 C2 119.2(2) . . ? C3 C4 C11 120.2(2) . . ? C6 C5 C11 121.2(2) . . ? C5 C6 C14 121.5(2) . . ? C8 C7 C14 119.9(2) . . ? C7 C8 C9 119.5(2) . . ? N10 C9 C8 122.0(2) . . ? C9 N10 C13 118.9(2) . . ? C9 N10 Zn1 126.53(14) . . ? C13 N10 Zn1 114.32(13) . . ? C12 C11 C4 117.0(2) . . ? C12 C11 C5 118.7(2) . . ? C4 C11 C5 124.2(2) . . ? N1 C12 C11 122.4(2) . . ? N1 C12 C13 117.5(2) . . ? C11 C12 C13 120.1(2) . . ? N10 C13 C14 122.5(2) . . ? N10 C13 C12 117.7(2) . . ? C14 C13 C12 119.8(2) . . ? C7 C14 C13 117.2(2) . . ? C7 C14 C6 124.2(2) . . ? C13 C14 C6 118.6(2) . . ? O2 C15 O1 124.4(2) . . ? O2 C15 C16 120.0(2) . . ? O1 C15 C16 115.6(2) . . ? C17 C16 C15 129.1(2) . . ? C17 C16 S1 111.42(15) . . ? C15 C16 S1 119.40(14) . . ? C16 C17 C18 113.0(2) . . ? C19 C18 C17 112.4(2) . . ? C18 C19 C20 130.2(2) . . ? C18 C19 S1 111.62(14) . . ? C20 C19 S1 118.14(14) . . ? O4 C20 O3 125.8(2) . 4_756 ? O4 C20 C19 116.9(2) . . ? O3 C20 C19 117.2(2) 4_756 . ? _refine_diff_density_max 0.282 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.081 data_cbl2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H12 Co N2 O5 S' _chemical_formula_weight 427.29 _chemical_melting_point ? _chemical_compound_source ? 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' 'Co' 'Co' 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting P2(1)/n _symmetry_space_group_name_H-M Monoclinic 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 10.917(2) _cell_length_b 15.711(2) _cell_length_c 11.330(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.01(3) _cell_angle_gamma 90.00 _cell_volume 1746.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method ? _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 1.136 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2928 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.88 _reflns_number_total 2272 _reflns_number_observed 1629 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0396P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0011(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2272 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_obs 0.0419 _refine_ls_wR_factor_all 0.0932 _refine_ls_wR_factor_obs 0.0865 _refine_ls_goodness_of_fit_all 0.915 _refine_ls_goodness_of_fit_obs 1.028 _refine_ls_restrained_S_all 0.915 _refine_ls_restrained_S_obs 1.028 _refine_ls_shift/esd_max -0.019 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Co1 Co 0.09432(6) 0.98529(4) 0.30252(6) 0.0337(2) Uani 1 d . . N1 N 0.2434(4) 1.0078(2) 0.4925(4) 0.0343(10) Uani 1 d . . C2 C 0.2411(5) 0.9830(3) 0.6036(5) 0.0433(13) Uani 1 d . . H2A H 0.1669(5) 0.9476(3) 0.5978(5) 0.080 Uiso 1 d R . C3 C 0.3415(6) 1.0064(3) 0.7265(5) 0.0528(15) Uani 1 d . . H3A H 0.3363(6) 0.9869(3) 0.8045(5) 0.080 Uiso 1 d R . C4 C 0.4466(5) 1.0566(4) 0.7356(5) 0.0527(15) Uani 1 d . . H4A H 0.5166(5) 1.0723(4) 0.8202(5) 0.080 Uiso 1 d R . C5 C 0.4531(5) 1.0857(3) 0.6203(5) 0.0406(13) Uani 1 d . . C6 C 0.3468(4) 1.0595(3) 0.5005(4) 0.0308(11) Uani 1 d . . C7 C 0.3445(5) 1.0874(3) 0.3781(5) 0.0358(12) Uani 1 d . . N8 N 0.2394(4) 1.0604(2) 0.2665(4) 0.0351(10) Uani 1 d . . C9 C 0.2364(5) 1.0855(3) 0.1536(5) 0.0427(13) Uani 1 d . . H9A H 0.1625(5) 1.0665(3) 0.0735(5) 0.080 Uiso 1 d R . C10 C 0.3362(5) 1.1380(3) 0.1471(5) 0.0515(14) Uani 1 d . . H10A H 0.3308(5) 1.1541(3) 0.0632(5) 0.080 Uiso 1 d R . C11 C 0.4409(6) 1.1669(3) 0.2584(5) 0.0529(15) Uani 1 d . . H11A H 0.5093(6) 1.2037(3) 0.2546(5) 0.080 Uiso 1 d R . C12 C 0.4476(5) 1.1415(3) 0.3811(5) 0.0405(13) Uani 1 d . . C13 C 0.5540(5) 1.1669(4) 0.5040(6) 0.055(2) Uani 1 d . . H13A H 0.6251(5) 1.2033(4) 0.5052(6) 0.080 Uiso 1 d R . C14 C 0.5557(5) 1.1402(3) 0.6180(6) 0.054(2) Uani 1 d . . H14A H 0.6276(5) 1.1588(3) 0.6998(6) 0.080 Uiso 1 d R . S1 S -0.20975(12) 1.22566(8) 0.25831(11) 0.0361(3) Uani 1 d . . C15 C -0.0987(5) 1.1082(3) 0.1507(5) 0.0340(12) Uani 1 d . . C16 C -0.1899(4) 1.1822(3) 0.1293(4) 0.0287(11) Uani 1 d . . C17 C -0.2721(5) 1.2223(3) 0.0143(4) 0.0376(12) Uani 1 d . . H17A H -0.2744(5) 1.2073(3) -0.0688(4) 0.080 Uiso 1 d R . C18 C -0.3522(5) 1.2872(3) 0.0291(4) 0.0369(12) Uani 1 d . . H18A H -0.4159(5) 1.3211(3) -0.0417(4) 0.080 Uiso 1 d R . C19 C -0.3289(4) 1.2969(3) 0.1578(4) 0.0306(11) Uani 1 d . . C20 C -0.3976(5) 1.3536(3) 0.2154(5) 0.0346(11) Uani 1 d . . O1 O -0.0294(3) 1.0855(2) 0.2690(3) 0.0399(8) Uani 1 d . . O2 O -0.0940(3) 1.0711(2) 0.0561(3) 0.0504(10) Uani 1 d . . O3 O -0.4864(3) 1.4043(2) 0.1377(3) 0.0423(9) Uani 1 d . . O4 O -0.3659(3) 1.3456(2) 0.3334(3) 0.0480(9) Uani 1 d . . O5 O 0.1015(4) 0.8942(3) 0.1777(4) 0.0445(11) Uani 1 d . . H5A H -0.0039(84) 0.8601(49) 0.1515(69) 0.161(32) Uiso 1 d . . H5B H 0.0959(63) 0.9060(40) 0.1202(52) 0.060(26) Uiso 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 Co1 0.0327(4) 0.0256(4) 0.0442(4) -0.0032(3) 0.0181(3) -0.0015(3) N1 0.033(2) 0.027(2) 0.045(2) 0.003(2) 0.020(2) 0.005(2) C2 0.051(3) 0.036(3) 0.050(3) 0.007(3) 0.029(3) 0.006(3) C3 0.059(4) 0.059(4) 0.038(3) 0.004(3) 0.019(3) 0.007(3) C4 0.045(3) 0.061(4) 0.042(3) -0.008(3) 0.010(3) 0.009(3) C5 0.037(3) 0.037(3) 0.042(3) -0.003(2) 0.011(3) 0.002(3) C6 0.030(3) 0.022(2) 0.044(3) -0.002(2) 0.019(2) 0.006(2) C7 0.035(3) 0.028(3) 0.045(3) -0.002(2) 0.019(3) 0.005(2) N8 0.032(2) 0.032(2) 0.039(2) -0.001(2) 0.013(2) -0.001(2) C9 0.041(3) 0.043(3) 0.042(3) 0.003(3) 0.018(3) -0.001(3) C10 0.052(4) 0.051(4) 0.063(4) 0.011(3) 0.036(3) -0.001(3) C11 0.049(4) 0.050(4) 0.069(4) 0.004(3) 0.035(3) -0.009(3) C12 0.032(3) 0.037(3) 0.053(3) -0.006(3) 0.019(3) -0.005(3) C13 0.038(3) 0.049(4) 0.077(4) -0.011(3) 0.025(3) -0.010(3) C14 0.039(3) 0.053(4) 0.059(4) -0.017(3) 0.010(3) -0.003(3) S1 0.0416(8) 0.0344(7) 0.0364(7) 0.0029(6) 0.0208(6) 0.0091(6) C15 0.032(3) 0.033(3) 0.044(3) 0.000(3) 0.024(3) -0.004(2) C16 0.030(3) 0.026(3) 0.033(3) 0.000(2) 0.017(2) 0.000(2) C17 0.043(3) 0.035(3) 0.036(3) 0.000(2) 0.018(2) 0.004(3) C18 0.038(3) 0.037(3) 0.035(3) 0.005(2) 0.016(2) 0.007(3) C19 0.027(3) 0.022(2) 0.046(3) 0.001(2) 0.019(2) 0.001(2) C20 0.034(3) 0.023(3) 0.048(3) 0.003(3) 0.019(3) 0.000(2) O1 0.046(2) 0.039(2) 0.041(2) 0.006(2) 0.024(2) 0.013(2) O2 0.070(3) 0.042(2) 0.050(2) -0.006(2) 0.036(2) 0.008(2) O3 0.046(2) 0.032(2) 0.055(2) 0.007(2) 0.028(2) 0.010(2) O4 0.049(2) 0.055(2) 0.041(2) 0.000(2) 0.020(2) 0.015(2) O5 0.056(3) 0.041(2) 0.043(3) -0.006(2) 0.028(2) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.000(3) . ? Co1 O5 2.038(4) . ? Co1 O3 2.042(3) 2_445 ? Co1 N1 2.082(4) . ? Co1 N8 2.152(4) . ? N1 C2 1.328(5) . ? N1 C6 1.361(5) . ? C2 C3 1.393(7) . ? C3 C4 1.359(7) . ? C4 C5 1.414(7) . ? C5 C6 1.407(6) . ? C5 C14 1.420(7) . ? C6 C7 1.443(6) . ? C7 N8 1.351(6) . ? C7 C12 1.399(6) . ? N8 C9 1.325(5) . ? C9 C10 1.394(6) . ? C10 C11 1.357(7) . ? C11 C12 1.418(6) . ? C12 C13 1.425(7) . ? C13 C14 1.349(7) . ? S1 C16 1.711(4) . ? S1 C19 1.715(4) . ? C15 O2 1.241(5) . ? C15 O1 1.267(5) . ? C15 C16 1.479(6) . ? C16 C17 1.370(6) . ? C17 C18 1.400(6) . ? C18 C19 1.374(6) . ? C19 C20 1.488(6) . ? C20 O4 1.232(5) . ? C20 O3 1.264(5) . ? O3 Co1 2.042(3) 2_455 ? 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 O1 Co1 O5 130.5(2) . . ? O1 Co1 O3 96.56(13) . 2_445 ? O5 Co1 O3 89.8(2) . 2_445 ? O1 Co1 N1 102.67(14) . . ? O5 Co1 N1 125.9(2) . . ? O3 Co1 N1 93.77(14) 2_445 . ? O1 Co1 N8 91.37(14) . . ? O5 Co1 N8 89.9(2) . . ? O3 Co1 N8 169.85(14) 2_445 . ? N1 Co1 N8 78.26(15) . . ? C2 N1 C6 118.2(4) . . ? C2 N1 Co1 126.8(3) . . ? C6 N1 Co1 114.8(3) . . ? N1 C2 C3 122.4(5) . . ? C4 C3 C2 119.8(5) . . ? C3 C4 C5 120.0(5) . . ? C6 C5 C4 116.3(5) . . ? C6 C5 C14 118.8(5) . . ? C4 C5 C14 124.9(5) . . ? N1 C6 C5 123.2(4) . . ? N1 C6 C7 117.0(4) . . ? C5 C6 C7 119.8(4) . . ? N8 C7 C12 123.9(4) . . ? N8 C7 C6 116.9(4) . . ? C12 C7 C6 119.1(4) . . ? C9 N8 C7 117.5(4) . . ? C9 N8 Co1 129.6(3) . . ? C7 N8 Co1 112.9(3) . . ? N8 C9 C10 122.6(5) . . ? C11 C10 C9 120.6(5) . . ? C10 C11 C12 118.5(5) . . ? C7 C12 C11 117.0(5) . . ? C7 C12 C13 119.7(5) . . ? C11 C12 C13 123.3(5) . . ? C14 C13 C12 120.8(5) . . ? C13 C14 C5 121.7(5) . . ? C16 S1 C19 92.1(2) . . ? O2 C15 O1 123.3(4) . . ? O2 C15 C16 120.5(4) . . ? O1 C15 C16 116.2(4) . . ? C17 C16 C15 129.1(4) . . ? C17 C16 S1 110.7(3) . . ? C15 C16 S1 120.1(3) . . ? C16 C17 C18 113.8(4) . . ? C19 C18 C17 111.9(4) . . ? C18 C19 C20 129.6(4) . . ? C18 C19 S1 111.5(3) . . ? C20 C19 S1 118.8(3) . . ? O4 C20 O3 125.8(4) . . ? O4 C20 C19 117.3(4) . . ? O3 C20 C19 116.8(4) . . ? C15 O1 Co1 117.6(3) . . ? C20 O3 Co1 122.6(3) . 2_455 ? _refine_diff_density_max 0.244 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.066 data_mkf39 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H10 Mn N2 O4 S' _chemical_formula_weight 405.28 _chemical_melting_point ? _chemical_compound_source ? 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' 'Mn' 'Mn' 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.031(2) _cell_length_b 18.113(6) _cell_length_c 21.755(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3165(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'Prismatic crystal fragment' _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method ? _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 0.995 _exptl_absorpt_correction_type Sadabs _exptl_absorpt_correction_T_min 0.709 _exptl_absorpt_correction_T_max 0.935 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16945 _diffrn_reflns_av_R_equivalents 0.0663 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 26.40 _reflns_number_total 3233 _reflns_number_observed 2192 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+2.2115P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3232 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_obs 0.0428 _refine_ls_wR_factor_all 0.1052 _refine_ls_wR_factor_obs 0.0874 _refine_ls_goodness_of_fit_all 1.054 _refine_ls_goodness_of_fit_obs 1.085 _refine_ls_restrained_S_all 1.058 _refine_ls_restrained_S_obs 1.085 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Mn Mn 0.74434(6) -0.00371(2) 0.69293(2) 0.02544(15) Uani 1 d . . S1 S 0.34896(11) -0.25849(4) 0.73543(4) 0.0319(2) Uani 1 d . . O1 O 0.5037(3) -0.05979(11) 0.69196(10) 0.0329(5) Uani 1 d . . O2 O 0.8363(3) -0.10135(11) 0.73358(11) 0.0400(6) Uani 1 d . . O3 O 0.9870(3) 0.05078(11) 0.67643(10) 0.0322(5) Uani 1 d . . O4 O 0.6901(3) 0.08064(11) 0.75771(10) 0.0355(6) Uani 1 d . . N1 N 0.8095(3) -0.05024(14) 0.59590(12) 0.0312(6) Uani 1 d . . C2 C 0.9024(4) -0.1095(2) 0.5844(2) 0.0374(9) Uani 1 d . . H2A H 0.9394(4) -0.1378(2) 0.6174(2) 0.045 Uiso 1 calc R . C3 C 0.9466(5) -0.1311(2) 0.5250(2) 0.0443(10) Uani 1 d . . H3A H 1.0111(5) -0.1731(2) 0.5189(2) 0.053 Uiso 1 calc R . C4 C 0.8946(5) -0.0902(2) 0.4761(2) 0.0429(9) Uani 1 d . . H4A H 0.9232(5) -0.1041(2) 0.4363(2) 0.051 Uiso 1 calc R . C5 C 0.7379(4) 0.0181(2) 0.4368(2) 0.0414(9) Uani 1 d . . H5A H 0.7630(4) 0.0059(2) 0.3963(2) 0.050 Uiso 1 calc R . C6 C 0.6454(5) 0.0782(2) 0.4490(2) 0.0443(9) Uani 1 d . . H6A H 0.6081(5) 0.1073(2) 0.4165(2) 0.053 Uiso 1 calc R . C7 C 0.5015(5) 0.1598(2) 0.5249(2) 0.0457(10) Uani 1 d . . H7A H 0.4635(5) 0.1908(2) 0.4939(2) 0.055 Uiso 1 calc R . C8 C 0.4594(5) 0.1734(2) 0.5845(2) 0.0469(10) Uani 1 d . . H8A H 0.3909(5) 0.2131(2) 0.5944(2) 0.056 Uiso 1 calc R . C9 C 0.5205(4) 0.1270(2) 0.6306(2) 0.0369(8) Uani 1 d . . H9A H 0.4899(4) 0.1363(2) 0.6711(2) 0.044 Uiso 1 calc R . N10 N 0.6197(3) 0.07038(14) 0.61926(12) 0.0293(6) Uani 1 d . . C11 C 0.6587(4) 0.0553(2) 0.55975(14) 0.0278(7) Uani 1 d . . C12 C 0.7585(4) -0.0093(2) 0.54685(14) 0.0289(7) Uani 1 d . . C13 C 0.7980(4) -0.0273(2) 0.4860(2) 0.0353(8) Uani 1 d . . C14 C 0.6027(4) 0.0987(2) 0.5103(2) 0.0341(8) Uani 1 d . . C15 C 0.4309(4) -0.1098(2) 0.72060(15) 0.0276(7) Uani 1 d . . C16 C 0.4545(4) -0.1878(2) 0.69978(13) 0.0251(7) Uani 1 d . . C17 C 0.5599(4) -0.2139(2) 0.65580(14) 0.0267(7) Uani 1 d . . H17A H 0.6264(4) -0.1837(2) 0.63142(14) 0.032 Uiso 1 calc R . C18 C 0.5577(4) -0.2916(2) 0.65111(13) 0.0275(7) Uani 1 d . . H18A H 0.6223(4) -0.3180(2) 0.62327(13) 0.033 Uiso 1 calc R . C19 C 0.4507(4) -0.3240(2) 0.69174(13) 0.0248(7) Uani 1 d . . C20 C 0.4231(4) -0.4041(2) 0.70448(14) 0.0259(7) Uani 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 Mn 0.0342(3) 0.0172(2) 0.0249(3) 0.0004(2) 0.0000(2) 0.0003(2) S1 0.0436(5) 0.0187(4) 0.0335(5) 0.0000(3) 0.0148(4) 0.0002(4) O1 0.0378(14) 0.0216(11) 0.0393(13) 0.0039(10) -0.0009(11) -0.0051(10) O2 0.056(2) 0.0219(11) 0.0421(15) 0.0065(10) -0.0191(13) -0.0023(11) O3 0.0388(14) 0.0219(11) 0.0359(13) -0.0051(9) 0.0026(11) -0.0053(10) O4 0.0464(15) 0.0233(11) 0.0368(13) -0.0077(10) 0.0117(12) -0.0016(11) N1 0.039(2) 0.0244(14) 0.030(2) -0.0018(12) 0.0023(13) -0.0031(13) C2 0.042(2) 0.028(2) 0.042(2) 0.001(2) 0.004(2) 0.000(2) C3 0.048(2) 0.033(2) 0.052(3) -0.008(2) 0.010(2) 0.007(2) C4 0.047(2) 0.047(2) 0.035(2) -0.012(2) 0.008(2) -0.006(2) C5 0.043(2) 0.058(2) 0.023(2) 0.000(2) 0.000(2) -0.008(2) C6 0.049(2) 0.052(2) 0.032(2) 0.010(2) -0.006(2) -0.003(2) C7 0.057(3) 0.039(2) 0.041(2) 0.010(2) -0.012(2) 0.004(2) C8 0.053(3) 0.034(2) 0.053(3) 0.002(2) -0.010(2) 0.013(2) C9 0.040(2) 0.032(2) 0.038(2) -0.004(2) 0.000(2) 0.006(2) N10 0.035(2) 0.0249(14) 0.0285(15) -0.0016(11) 0.0009(13) -0.0005(13) C11 0.029(2) 0.024(2) 0.030(2) 0.0003(13) -0.0019(15) -0.0046(15) C12 0.029(2) 0.029(2) 0.029(2) 0.0005(14) 0.000(2) -0.0082(15) C13 0.034(2) 0.038(2) 0.034(2) -0.003(2) 0.003(2) -0.007(2) C14 0.034(2) 0.036(2) 0.032(2) 0.004(2) -0.006(2) -0.004(2) C15 0.031(2) 0.021(2) 0.030(2) 0.0018(13) -0.003(2) -0.0010(14) C16 0.031(2) 0.0198(15) 0.025(2) 0.0022(12) 0.0030(15) -0.0027(13) C17 0.029(2) 0.026(2) 0.025(2) 0.0042(13) 0.0010(14) -0.0030(14) C18 0.032(2) 0.029(2) 0.022(2) -0.0046(13) 0.0055(14) 0.0016(15) C19 0.030(2) 0.0218(15) 0.023(2) -0.0033(12) 0.0021(14) 0.0021(13) C20 0.035(2) 0.020(2) 0.023(2) 0.0003(13) -0.0077(15) 0.0004(14) _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 Mn O2 2.111(2) . ? Mn O4 2.124(2) . ? Mn O1 2.183(2) . ? Mn O3 2.214(2) . ? Mn N10 2.317(3) . ? Mn N1 2.332(3) . ? S1 C16 1.721(3) . ? S1 C19 1.726(3) . ? O1 C15 1.245(4) . ? O2 C15 1.262(4) 6_657 ? O3 C20 1.250(4) 8_765 ? O4 C20 1.256(4) 3_656 ? N1 C2 1.331(4) . ? N1 C12 1.362(4) . ? C2 C3 1.396(5) . ? C3 C4 1.362(5) . ? C4 C13 1.395(5) . ? C5 C6 1.345(5) . ? C5 C13 1.434(5) . ? C6 C14 1.426(5) . ? C7 C8 1.363(5) . ? C7 C14 1.410(5) . ? C8 C9 1.398(5) . ? C9 N10 1.322(4) . ? N10 C11 1.360(4) . ? C11 C14 1.406(4) . ? C11 C12 1.447(4) . ? C12 C13 1.399(4) . ? C15 O2 1.262(4) 6_557 ? C15 C16 1.496(4) . ? C16 C17 1.363(4) . ? C17 C18 1.412(4) . ? C18 C19 1.365(4) . ? C19 C20 1.494(4) . ? C20 O3 1.250(4) 8_755 ? C20 O4 1.256(4) 3_646 ? 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 Mn O4 113.36(9) . . ? O2 Mn O1 85.64(9) . . ? O4 Mn O1 99.18(9) . . ? O2 Mn O3 97.67(9) . . ? O4 Mn O3 88.13(9) . . ? O1 Mn O3 170.08(8) . . ? O2 Mn N10 157.82(9) . . ? O4 Mn N10 87.35(9) . . ? O1 Mn N10 83.14(9) . . ? O3 Mn N10 90.56(9) . . ? O2 Mn N1 89.88(9) . . ? O4 Mn N1 155.03(9) . . ? O1 Mn N1 91.25(9) . . ? O3 Mn N1 79.45(9) . . ? N10 Mn N1 71.35(9) . . ? C16 S1 C19 91.75(15) . . ? C15 O1 Mn 138.5(2) . . ? C15 O2 Mn 130.0(2) 6_657 . ? C20 O3 Mn 136.1(2) 8_765 . ? C20 O4 Mn 137.8(2) 3_656 . ? C2 N1 C12 117.4(3) . . ? C2 N1 Mn 126.0(2) . . ? C12 N1 Mn 116.4(2) . . ? N1 C2 C3 122.9(3) . . ? C4 C3 C2 119.5(3) . . ? C3 C4 C13 119.6(3) . . ? C6 C5 C13 120.2(3) . . ? C5 C6 C14 121.8(3) . . ? C8 C7 C14 120.0(3) . . ? C7 C8 C9 119.0(3) . . ? N10 C9 C8 123.0(3) . . ? C9 N10 C11 118.2(3) . . ? C9 N10 Mn 125.5(2) . . ? C11 N10 Mn 116.3(2) . . ? N10 C11 C14 122.9(3) . . ? N10 C11 C12 118.3(3) . . ? C14 C11 C12 118.8(3) . . ? N1 C12 C13 123.1(3) . . ? N1 C12 C11 117.1(3) . . ? C13 C12 C11 119.8(3) . . ? C4 C13 C12 117.5(3) . . ? C4 C13 C5 122.7(3) . . ? C12 C13 C5 119.8(3) . . ? C11 C14 C7 116.8(3) . . ? C11 C14 C6 119.6(3) . . ? C7 C14 C6 123.6(3) . . ? O1 C15 O2 126.2(3) . 6_557 ? O1 C15 C16 118.4(3) . . ? O2 C15 C16 115.4(3) 6_557 . ? C17 C16 C15 128.3(3) . . ? C17 C16 S1 111.3(2) . . ? C15 C16 S1 120.3(2) . . ? C16 C17 C18 112.9(3) . . ? C19 C18 C17 112.9(3) . . ? C18 C19 C20 129.1(3) . . ? C18 C19 S1 111.1(2) . . ? C20 C19 S1 119.7(2) . . ? O3 C20 O4 126.5(3) 8_755 3_646 ? O3 C20 C19 117.3(3) 8_755 . ? O4 C20 C19 116.2(3) 3_646 . ? _refine_diff_density_max 0.344 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.071 data_mkf44a _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C6 H6 Mn O6 S' _chemical_formula_weight 261.11 _chemical_melting_point ? _chemical_compound_source ? 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' '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' 'Mn' 'Mn' 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Pnma _symmetry_space_group_name_H-M Orthorhombic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 7.349(1) _cell_length_b 18.165(1) _cell_length_c 6.721(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 897.3(1) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.933 _exptl_crystal_density_method ? _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 1.703 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4703 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.35 _reflns_number_total 947 _reflns_number_observed 873 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.2343P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 947 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_obs 0.0238 _refine_ls_wR_factor_all 0.0612 _refine_ls_wR_factor_obs 0.0602 _refine_ls_goodness_of_fit_all 1.108 _refine_ls_goodness_of_fit_obs 1.139 _refine_ls_restrained_S_all 1.108 _refine_ls_restrained_S_obs 1.139 _refine_ls_shift/esd_max 0.003 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Mn1 Mn 0.5000 0.5000 0.0000 0.02023(14) Uani 1 d S . S1 S 0.71127(8) 0.7500 0.16003(8) 0.0226(2) Uani 1 d S . O3 O 0.6738(2) 0.58879(6) 0.1061(2) 0.0294(3) Uani 1 d . . O2 O 0.4868(2) 0.55882(8) -0.2846(2) 0.0318(3) Uani 1 d . . H2A H 0.5746(35) 0.5659(14) -0.3627(37) 0.052(7) Uiso 1 d . . H2B H 0.4154(51) 0.5495(20) -0.3583(50) 0.096(13) Uiso 1 d . . O1 O 0.25177(15) 0.55620(6) 0.0851(2) 0.0252(3) Uani 1 d . . C1 C 0.7226(2) 0.60401(8) 0.2801(2) 0.0192(3) Uani 1 d . . C2 C 0.7418(2) 0.68271(8) 0.3354(2) 0.0210(3) Uani 1 d . . C3 C 0.7739(3) 0.71134(10) 0.5214(2) 0.0282(4) Uani 1 d . . H3A H 0.8014(30) 0.6811(12) 0.6398(34) 0.045(6) Uiso 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 Mn1 0.0231(2) 0.0151(2) 0.0225(2) -0.00262(11) 0.00399(12) 0.00031(11) S1 0.0333(3) 0.0144(3) 0.0202(3) 0.000 -0.0063(2) 0.000 O3 0.0438(7) 0.0186(6) 0.0258(6) -0.0017(4) -0.0062(5) -0.0048(5) O2 0.0318(7) 0.0393(8) 0.0244(6) 0.0020(5) -0.0007(5) -0.0034(5) O1 0.0280(6) 0.0166(6) 0.0311(6) -0.0058(4) 0.0048(5) 0.0017(4) C1 0.0183(6) 0.0143(7) 0.0251(7) 0.0000(6) -0.0008(6) 0.0010(5) C2 0.0236(7) 0.0150(7) 0.0242(8) 0.0019(6) -0.0042(6) 0.0002(5) C3 0.0399(9) 0.0203(9) 0.0245(8) 0.0025(6) -0.0076(7) 0.0003(7) _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 Mn1 O1 2.1672(11) . ? Mn1 O1 2.1673(11) 5_665 ? Mn1 O3 2.1776(11) . ? Mn1 O3 2.1776(11) 5_665 ? Mn1 O2 2.1931(14) . ? Mn1 O2 2.1931(14) 5_665 ? S1 C2 1.7129(15) . ? S1 C2 1.7129(15) 7_575 ? O3 C1 1.254(2) . ? O1 C1 1.273(2) 6_556 ? C1 O1 1.274(2) 6_656 ? C1 C2 1.484(2) . ? C2 C3 1.374(2) . ? C3 C3 1.405(3) 7_575 ? 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 O1 Mn1 O1 180.0 . 5_665 ? O1 Mn1 O3 93.35(4) . . ? O1 Mn1 O3 86.65(4) 5_665 . ? O1 Mn1 O3 86.65(4) . 5_665 ? O1 Mn1 O3 93.35(4) 5_665 5_665 ? O3 Mn1 O3 180.0 . 5_665 ? O1 Mn1 O2 87.90(5) . . ? O1 Mn1 O2 92.10(5) 5_665 . ? O3 Mn1 O2 87.17(5) . . ? O3 Mn1 O2 92.83(5) 5_665 . ? O1 Mn1 O2 92.10(5) . 5_665 ? O1 Mn1 O2 87.90(5) 5_665 5_665 ? O3 Mn1 O2 92.83(5) . 5_665 ? O3 Mn1 O2 87.17(5) 5_665 5_665 ? O2 Mn1 O2 180.0 . 5_665 ? C2 S1 C2 91.05(10) . 7_575 ? C1 O3 Mn1 129.54(10) . . ? C1 O1 Mn1 130.59(10) 6_556 . ? O3 C1 O1 124.15(14) . 6_656 ? O3 C1 C2 118.25(13) . . ? O1 C1 C2 117.57(14) 6_656 . ? C3 C2 C1 127.51(14) . . ? C3 C2 S1 112.24(12) . . ? C1 C2 S1 120.17(11) . . ? C2 C3 C3 112.24(9) . 7_575 ? _refine_diff_density_max 0.277 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.070