#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/33/2013373.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2013373 loop_ _publ_author_name 'Liang Shen' _publ_section_title ; Diaqua(2,2'-bipyridine)malonatomanganese(II) ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first m128 _journal_page_last m129 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac '[Mn (C3 H2 O4) (C10 H8 N2) (H2 O)2]' _chemical_formula_moiety 'C13 H14 Mn N2 O6' _chemical_formula_sum 'C13 H14 Mn N2 O6' _chemical_formula_weight 349.20 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 97.75(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.834(2) _cell_length_b 9.408(2) _cell_length_c 20.532(4) _cell_measurement_reflns_used 26 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 14.77 _cell_measurement_theta_min 3.66 _cell_volume 1499.4(6) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS User's Manual (Siemens, 1991)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990a)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990b)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0100 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 3153 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.00 _diffrn_standards_decay_% 2.56 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.910 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_correction_T_min 0.8432 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 716 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.38 _refine_diff_density_max 0.565 _refine_diff_density_min -0.378 _refine_ls_extinction_coef 0.0055(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 216 _refine_ls_number_reflns 2647 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0311 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.4939P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0772 _refine_ls_wR_factor_ref 0.0797 _reflns_number_gt 2210 _reflns_number_total 2647 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sq1008.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2013373 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Mn 0.18242(4) 0.41635(4) 0.328984(15) 0.03395(14) Uani d . 1 . . Mn O1 0.1359(2) 0.53713(19) 0.23848(7) 0.0452(4) Uani d . 1 . . O O2 0.1992(3) 0.6244(2) 0.14481(8) 0.0577(5) Uani d . 1 . . O O3 0.4472(2) 0.43297(19) 0.31814(8) 0.0505(4) Uani d . 1 . . O O4 0.6497(2) 0.5458(3) 0.27577(11) 0.0861(8) Uani d . 1 . . O O5 -0.0881(2) 0.3901(2) 0.33636(10) 0.0518(5) Uani d D 1 . . O O6 0.1673(2) 0.1952(2) 0.29776(10) 0.0509(5) Uani d D 1 . . O N1 0.1735(3) 0.6162(2) 0.39192(9) 0.0419(5) Uani d . 1 . . N N2 0.2592(2) 0.3530(2) 0.43586(9) 0.0408(5) Uani d . 1 . . N C1 0.1257(4) 0.7445(3) 0.36856(13) 0.0572(7) Uani d . 1 . . C H1 0.1061 0.7571 0.3232 0.069 Uiso calc R 1 . . H C2 0.1042(4) 0.8591(3) 0.40821(16) 0.0696(9) Uani d . 1 . . C H2 0.0697 0.9469 0.3902 0.084 Uiso calc R 1 . . H C3 0.1349(4) 0.8405(3) 0.47485(15) 0.0704(9) Uani d . 1 . . C H3 0.1219 0.9160 0.5030 0.085 Uiso calc R 1 . . H C4 0.1846(4) 0.7102(3) 0.49965(13) 0.0593(7) Uani d . 1 . . C H4 0.2055 0.6963 0.5449 0.071 Uiso calc R 1 . . H C5 0.2040(3) 0.5984(2) 0.45720(11) 0.0394(5) Uani d . 1 . . C C6 0.2613(3) 0.4555(3) 0.48113(10) 0.0388(5) Uani d . 1 . . C C7 0.3198(4) 0.4287(3) 0.54682(12) 0.0578(7) Uani d . 1 . . C H7 0.3232 0.5013 0.5777 0.069 Uiso calc R 1 . . H C8 0.3725(4) 0.2948(3) 0.56571(13) 0.0702(9) Uani d . 1 . . C H8 0.4118 0.2755 0.6096 0.084 Uiso calc R 1 . . H C9 0.3670(4) 0.1897(3) 0.51982(15) 0.0717(9) Uani d . 1 . . C H9 0.4006 0.0975 0.5319 0.086 Uiso calc R 1 . . H C10 0.3108(4) 0.2230(3) 0.45527(13) 0.0590(7) Uani d . 1 . . C H10 0.3087 0.1516 0.4238 0.071 Uiso calc R 1 . . H C11 0.2343(3) 0.5513(2) 0.19476(11) 0.0391(5) Uani d . 1 . . C C12 0.4020(4) 0.4679(4) 0.20319(13) 0.0615(8) Uani d . 1 . . C H12A 0.3760 0.3680 0.1956 0.074 Uiso calc R 1 . . H H12B 0.4714 0.4989 0.1701 0.074 Uiso calc R 1 . . H C13 0.5063(3) 0.4845(3) 0.27045(12) 0.0493(6) Uani d . 1 . . C H5A -0.124(3) 0.3108(15) 0.3425(13) 0.053(9) Uiso d D 1 . . H H5B -0.167(3) 0.439(3) 0.3190(13) 0.062(9) Uiso d D 1 . . H H6A 0.231(3) 0.156(3) 0.2750(13) 0.071(10) Uiso d D 1 . . H H6B 0.073(2) 0.156(3) 0.2896(15) 0.083(11) Uiso d D 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Mn 0.0348(2) 0.0395(2) 0.02761(19) -0.00011(15) 0.00448(13) -0.00203(15) O1 0.0401(9) 0.0640(11) 0.0321(8) 0.0119(8) 0.0071(7) 0.0093(8) O2 0.0779(13) 0.0587(11) 0.0378(10) 0.0101(10) 0.0124(9) 0.0138(8) O3 0.0337(8) 0.0704(12) 0.0465(10) -0.0058(8) 0.0027(7) 0.0120(9) O4 0.0374(11) 0.1198(19) 0.0992(17) -0.0124(12) 0.0022(10) 0.0655(15) O5 0.0355(10) 0.0494(12) 0.0714(13) 0.0032(9) 0.0109(9) 0.0057(10) O6 0.0392(10) 0.0502(11) 0.0656(12) -0.0043(9) 0.0153(9) -0.0233(9) N1 0.0512(12) 0.0383(11) 0.0351(10) 0.0015(9) 0.0015(9) -0.0021(8) N2 0.0480(11) 0.0391(11) 0.0345(10) 0.0000(9) 0.0030(8) 0.0006(9) C1 0.0738(19) 0.0442(15) 0.0488(15) 0.0077(14) -0.0088(13) 0.0011(12) C2 0.084(2) 0.0421(15) 0.078(2) 0.0154(15) -0.0073(17) -0.0045(15) C3 0.090(2) 0.0525(18) 0.068(2) 0.0141(16) 0.0091(17) -0.0224(15) C4 0.079(2) 0.0584(18) 0.0418(14) 0.0069(15) 0.0118(13) -0.0115(13) C5 0.0419(12) 0.0435(13) 0.0332(12) -0.0008(10) 0.0072(10) -0.0056(10) C6 0.0406(12) 0.0462(14) 0.0304(11) -0.0059(10) 0.0081(9) -0.0009(10) C7 0.0784(19) 0.0616(18) 0.0323(13) -0.0012(15) 0.0033(12) -0.0002(12) C8 0.095(2) 0.074(2) 0.0389(15) -0.0011(18) -0.0034(15) 0.0157(15) C9 0.094(2) 0.0554(18) 0.0608(18) 0.0082(17) -0.0074(16) 0.0188(15) C10 0.0780(19) 0.0466(16) 0.0492(15) 0.0066(14) -0.0030(14) 0.0005(12) C11 0.0452(13) 0.0416(13) 0.0300(11) -0.0010(10) 0.0029(10) -0.0045(10) C12 0.0579(17) 0.086(2) 0.0446(14) 0.0178(15) 0.0210(13) 0.0049(14) C13 0.0332(13) 0.0615(16) 0.0537(15) 0.0086(12) 0.0072(11) 0.0185(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Mn O3 . 2.1215(17) yes Mn O5 . 2.1595(19) yes Mn O1 . 2.1667(16) yes Mn O6 . 2.1757(19) yes Mn N2 . 2.2751(19) yes Mn N1 . 2.2877(19) yes O1 C11 . 1.267(3) yes O2 C11 . 1.235(3) yes O3 C13 . 1.237(3) yes O4 C13 . 1.255(3) yes O5 H5A . 0.814(10) ? O5 H5B . 0.816(10) ? O6 H6A . 0.816(10) ? O6 H6B . 0.820(10) ? N1 C1 . 1.334(3) ? N1 C5 . 1.340(3) ? N2 C10 . 1.333(3) ? N2 C6 . 1.338(3) ? C1 C2 . 1.375(4) ? C1 H1 . 0.9300 ? C2 C3 . 1.368(4) ? C2 H2 . 0.9300 ? C3 C4 . 1.364(4) ? C3 H3 . 0.9300 ? C4 C5 . 1.387(3) ? C4 H4 . 0.9300 ? C5 C6 . 1.480(3) ? C6 C7 . 1.388(3) ? C7 C8 . 1.365(4) ? C7 H7 . 0.9300 ? C8 C9 . 1.363(4) ? C8 H8 . 0.9300 ? C9 C10 . 1.375(4) ? C9 H9 . 0.9300 ? C10 H10 . 0.9300 ? C11 C12 . 1.520(3) ? C12 C13 . 1.515(4) ? C12 H12A . 0.9700 ? C12 H12B . 0.9700 ? 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O3 Mn O5 176.94(7) yes O3 Mn O1 85.70(6) yes O5 Mn O1 93.85(7) yes O3 Mn O6 93.13(7) yes O5 Mn O6 84.04(7) yes O1 Mn O6 104.64(7) yes O3 Mn N2 89.17(7) yes O5 Mn N2 92.09(8) yes O1 Mn N2 163.06(7) yes O6 Mn N2 91.74(7) yes O3 Mn N1 95.95(7) yes O5 Mn N1 87.10(7) yes O1 Mn N1 92.24(7) yes O6 Mn N1 161.39(7) yes N2 Mn N1 72.22(7) yes C11 O1 Mn 127.96(15) ? C13 O3 Mn 125.98(16) ? Mn O5 H5A 119(2) ? Mn O5 H5B 127(2) ? H5A O5 H5B 109(3) ? Mn O6 H6A 126(2) ? Mn O6 H6B 120(2) ? H6A O6 H6B 107(3) ? C1 N1 C5 118.4(2) ? C1 N1 Mn 124.69(16) ? C5 N1 Mn 116.59(15) ? C10 N2 C6 118.6(2) ? C10 N2 Mn 123.99(16) ? C6 N2 Mn 117.26(15) ? N1 C1 C2 123.2(2) ? N1 C1 H1 118.4 ? C2 C1 H1 118.4 ? C3 C2 C1 118.2(3) ? C3 C2 H2 120.9 ? C1 C2 H2 120.9 ? C4 C3 C2 119.4(3) ? C4 C3 H3 120.3 ? C2 C3 H3 120.3 ? C3 C4 C5 119.8(3) ? C3 C4 H4 120.1 ? C5 C4 H4 120.1 ? N1 C5 C4 120.9(2) ? N1 C5 C6 116.79(19) ? C4 C5 C6 122.3(2) ? N2 C6 C7 121.0(2) ? N2 C6 C5 116.70(19) ? C7 C6 C5 122.2(2) ? C8 C7 C6 119.4(3) ? C8 C7 H7 120.3 ? C6 C7 H7 120.3 ? C9 C8 C7 119.5(3) ? C9 C8 H8 120.2 ? C7 C8 H8 120.2 ? C8 C9 C10 118.5(3) ? C8 C9 H9 120.7 ? C10 C9 H9 120.7 ? N2 C10 C9 122.8(3) ? N2 C10 H10 118.6 ? C9 C10 H10 118.6 ? O2 C11 O1 123.9(2) ? O2 C11 C12 118.3(2) ? O1 C11 C12 117.7(2) ? C13 C12 C11 113.7(2) ? C13 C12 H12A 108.8 ? C11 C12 H12A 108.8 ? C13 C12 H12B 108.8 ? C11 C12 H12B 108.8 ? H12A C12 H12B 107.7 ? O3 C13 O4 122.5(2) ? O3 C13 C12 117.9(2) ? O4 C13 C12 119.5(2) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O5 H5A O2 2_545 0.81(2) 1.88(2) 2.692(3) 178(2) yes O5 H5B O4 1_455 0.81(3) 1.88(3) 2.688(3) 177(3) yes O6 H6A O2 2_645 0.82(3) 1.82(3) 2.626(3) 171(3) yes O6 H6B O4 2_545 0.82(2) 2.00(2) 2.816(3) 179(3) yes 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 O3 Mn O1 C11 21.2(2) O5 Mn O1 C11 -155.8(2) O6 Mn O1 C11 -70.9(2) N2 Mn O1 C11 93.9(3) N1 Mn O1 C11 117.0(2) O5 Mn O3 C13 75.8(14) O1 Mn O3 C13 -5.9(2) O6 Mn O3 C13 98.6(2) N2 Mn O3 C13 -169.7(2) N1 Mn O3 C13 -97.7(2) O3 Mn N1 C1 94.7(2) O5 Mn N1 C1 -84.9(2) O1 Mn N1 C1 8.8(2) O6 Mn N1 C1 -146.5(2) N2 Mn N1 C1 -178.1(2) O3 Mn N1 C5 -91.46(17) O5 Mn N1 C5 88.89(17) O1 Mn N1 C5 -177.36(17) O6 Mn N1 C5 27.3(3) N2 Mn N1 C5 -4.24(16) O3 Mn N2 C10 -79.3(2) O5 Mn N2 C10 98.0(2) O1 Mn N2 C10 -151.5(2) O6 Mn N2 C10 13.9(2) N1 Mn N2 C10 -175.8(2) O3 Mn N2 C6 96.83(17) O5 Mn N2 C6 -85.96(17) O1 Mn N2 C6 24.6(3) O6 Mn N2 C6 -170.06(16) N1 Mn N2 C6 0.32(16) C5 N1 C1 C2 -0.8(4) Mn N1 C1 C2 172.9(2) N1 C1 C2 C3 0.6(5) C1 C2 C3 C4 -0.2(5) C2 C3 C4 C5 0.2(5) C1 N1 C5 C4 0.7(4) Mn N1 C5 C4 -173.5(2) C1 N1 C5 C6 -178.4(2) Mn N1 C5 C6 7.4(3) C3 C4 C5 N1 -0.4(4) C3 C4 C5 C6 178.6(3) C10 N2 C6 C7 1.6(4) Mn N2 C6 C7 -174.75(19) C10 N2 C6 C5 179.6(2) Mn N2 C6 C5 3.3(3) N1 C5 C6 N2 -7.2(3) C4 C5 C6 N2 173.7(2) N1 C5 C6 C7 170.8(2) C4 C5 C6 C7 -8.3(4) N2 C6 C7 C8 -1.5(4) C5 C6 C7 C8 -179.4(3) C6 C7 C8 C9 0.1(5) C7 C8 C9 C10 1.1(5) C6 N2 C10 C9 -0.3(4) Mn N2 C10 C9 175.7(2) C8 C9 C10 N2 -1.0(5) Mn O1 C11 O2 -178.73(17) Mn O1 C11 C12 4.0(3) O2 C11 C12 C13 132.2(3) O1 C11 C12 C13 -50.4(3) Mn O3 C13 O4 149.2(2) Mn O3 C13 C12 -32.8(3) C11 C12 C13 O3 67.8(3) C11 C12 C13 O4 -114.1(3) _cod_database_fobs_code 2013373 _journal_paper_doi 10.1107/S0108270103004244