data_ull2235 _audit_creation_method SHELXL-97 _publ_contact_author_name "Professor Catalina Ruiz-P\'erez" _publ_contact_author_address ;Laboratorio de Rayos X y Materiales Moleculares Dpto. F\'isica Fundamental II. Facultad de F\'isica Universidad de La Laguna E-38204. La Laguna. Tenerife Spain ; _publ_contact_author_email caruiz@ull.es _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Mn N2 O5' _chemical_formula_weight 319.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnnm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z' '-x-1/2, y-1/2, z-1/2' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.2570(3) _cell_length_b 25.9657(10) _cell_length_c 7.5506(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1422.78(10) _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 Prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 7.746 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_min 0.3177 _exptl_absorpt_correction_T_max 0.3874 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator 'mirror' _diffrn_radiation_probe x-ray _diffrn_source ? _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.5953 _diffrn_measurement_device ? _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3427 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 75.71 _reflns_number_total 1563 _reflns_number_gt 1370 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1414P)^2^+2.1592P] 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 0.0029(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1563 _refine_ls_number_parameters 117 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.2403 _refine_ls_wR_factor_gt 0.2326 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 Mn1 Mn 0.01636(14) 0.78175(4) 1.0000 0.0363(4) Uani 1 2 d S . . O2 O -0.1557(5) 0.74154(14) 0.8140(4) 0.0506(9) Uani 1 1 d . . . O1 O -0.3412(5) 0.68092(13) 0.7152(5) 0.0499(9) Uani 1 1 d . . . O1W O 0.2230(8) 0.71891(19) 1.0000 0.0460(12) Uani 1 2 d SD . . N1 N -0.1783(8) 0.8512(2) 1.0000 0.0487(14) Uani 1 2 d S . . N2 N -0.5357(10) 0.9786(3) 1.0000 0.070(2) Uani 1 2 d S . . C11 C -0.1117(11) 0.8983(3) 1.0000 0.065(2) Uani 1 2 d S . . H11 H 0.0157 0.9024 1.0000 0.078 Uiso 1 2 calc SR . . C7 C -0.3603(11) 0.8460(3) 1.0000 0.067(3) Uani 1 2 d S . . H7 H -0.4102 0.8130 1.0000 0.080 Uiso 1 2 calc SR . . C8 C -0.4795(11) 0.8880(4) 1.0000 0.081(4) Uani 1 2 d S . . H8 H -0.6064 0.8829 1.0000 0.097 Uiso 1 2 calc SR . . C2 C -0.2031(11) 0.6677(3) 1.0000 0.0462(16) Uani 1 2 d S . . H2 H -0.0701 0.6612 1.0000 0.055 Uiso 1 2 calc SR . . C1 C -0.2397(6) 0.69925(17) 0.8311(6) 0.0381(10) Uani 1 1 d . . . C9 C -0.4093(11) 0.9366(3) 1.0000 0.060(2) Uani 1 2 d S . . C10 C -0.2195(11) 0.9422(3) 1.0000 0.064(2) Uani 1 2 d S . . H10 H -0.1658 0.9748 1.0000 0.076 Uiso 1 2 calc SR . . C3 C -0.2914(15) 0.6152(3) 1.0000 0.062(2) Uani 1 2 d S . . H3A H -0.2503 0.5964 0.8963 0.075 Uiso 0.50 1 d PR . . C4 C -0.505(3) 0.6170(7) 1.0000 0.123(6) Uani 1 2 d S . . H4A H -0.5461 0.6357 0.8962 0.148 Uiso 0.50 1 d PR . . C5 C -0.599(4) 0.5630(9) 1.0000 0.195(12) Uani 1 2 d S . . H5A H -0.5536 0.5447 0.8967 0.234 Uiso 0.50 1 d PR . . C6 C -0.817(4) 0.5617(11) 1.0000 0.226(15) Uani 1 2 d S . . H6A H -0.8522 0.5261 1.0000 0.339 Uiso 1 2 d SR . . H6B H -0.8653 0.5782 0.8962 0.339 Uiso 0.50 1 d PR . . H1WB H 0.297(8) 0.727(3) 0.911(7) 0.08(2) Uiso 1 1 d 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 0.0354(6) 0.0421(7) 0.0315(6) 0.000 0.000 0.0024(4) O2 0.061(2) 0.054(2) 0.0365(17) 0.0054(15) -0.0116(16) -0.0132(17) O1 0.058(2) 0.0481(18) 0.0437(18) 0.0016(15) -0.0151(17) -0.0053(16) O1W 0.049(3) 0.050(3) 0.040(3) 0.000 0.000 0.007(2) N1 0.042(3) 0.046(3) 0.058(4) 0.000 0.000 0.013(2) N2 0.045(4) 0.049(3) 0.115(7) 0.000 0.000 0.013(3) C11 0.039(4) 0.050(4) 0.105(7) 0.000 0.000 0.005(3) C7 0.041(4) 0.046(4) 0.114(8) 0.000 0.000 0.005(3) C8 0.038(4) 0.049(5) 0.155(12) 0.000 0.000 0.003(3) C2 0.059(4) 0.044(3) 0.036(3) 0.000 0.000 0.008(3) C1 0.042(2) 0.042(2) 0.0309(19) -0.0033(18) 0.0011(18) 0.0031(18) C9 0.042(4) 0.047(4) 0.092(6) 0.000 0.000 0.009(3) C10 0.045(4) 0.044(4) 0.102(7) 0.000 0.000 0.005(3) C3 0.086(6) 0.045(4) 0.057(5) 0.000 0.000 0.004(4) C4 0.144(16) 0.094(10) 0.133(15) 0.000 0.000 -0.007(9) C5 0.21(3) 0.117(15) 0.26(3) 0.000 0.000 -0.057(18) C6 0.20(3) 0.23(3) 0.26(4) 0.000 0.000 -0.11(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 Mn1 O2 2.150(3) . ? Mn1 O2 2.150(3) 6_557 ? Mn1 O1 2.156(4) 8_676 ? Mn1 O1 2.156(4) 3_566 ? Mn1 O1W 2.216(5) . ? Mn1 N1 2.290(6) . ? O2 C1 1.262(6) . ? O1 C1 1.239(6) . ? O1 Mn1 2.156(3) 3_466 ? N1 C11 1.316(10) . ? N1 C7 1.328(10) . ? N2 N2 1.228(16) 5_477 ? N2 C9 1.424(10) . ? C11 C10 1.383(11) . ? C7 C8 1.392(12) . ? C8 C9 1.362(12) . ? C2 C3 1.506(11) . ? C2 C1 1.539(6) . ? C2 C1 1.539(6) 6_557 ? C9 C10 1.385(11) . ? C3 C4 1.548(19) . ? C4 C5 1.56(3) . ? C5 C6 1.58(4) . ? 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 Mn1 O2 81.6(2) . 6_557 ? O2 Mn1 O1 171.55(15) . 8_676 ? O2 Mn1 O1 90.26(15) 6_557 8_676 ? O2 Mn1 O1 90.26(15) . 3_566 ? O2 Mn1 O1 171.55(15) 6_557 3_566 ? O1 Mn1 O1 97.8(2) 8_676 3_566 ? O2 Mn1 O1W 92.04(16) . . ? O2 Mn1 O1W 92.04(16) 6_557 . ? O1 Mn1 O1W 90.38(14) 8_676 . ? O1 Mn1 O1W 90.38(14) 3_566 . ? O2 Mn1 N1 91.36(17) . . ? O2 Mn1 N1 91.36(17) 6_557 . ? O1 Mn1 N1 86.67(14) 8_676 . ? O1 Mn1 N1 86.67(14) 3_566 . ? O1W Mn1 N1 175.5(2) . . ? C1 O2 Mn1 129.5(3) . . ? C1 O1 Mn1 130.1(3) . 3_466 ? C11 N1 C7 117.4(7) . . ? C11 N1 Mn1 120.4(5) . . ? C7 N1 Mn1 122.3(5) . . ? N2 N2 C9 114.9(9) 5_477 . ? N1 C11 C10 124.0(8) . . ? N1 C7 C8 122.6(8) . . ? C9 C8 C7 119.6(8) . . ? C3 C2 C1 114.1(4) . . ? C3 C2 C1 114.1(4) . 6_557 ? C1 C2 C1 111.9(5) . 6_557 ? O1 C1 O2 123.3(4) . . ? O1 C1 C2 118.9(5) . . ? O2 C1 C2 117.7(4) . . ? C8 C9 C10 118.0(7) . . ? C8 C9 N2 117.9(7) . . ? C10 C9 N2 124.1(8) . . ? C11 C10 C9 118.4(8) . . ? C2 C3 C4 113.5(9) . . ? C3 C4 C5 114.3(17) . . ? C4 C5 C6 117(2) . . ? 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 O1W H1WB O2 0.89(2) 1.91(4) 2.730(4) 152(7) 3_566 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 75.71 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.088 _refine_diff_density_min -0.688 _refine_diff_density_rms 0.131