# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Srinivasan Natarajan' _publ_contact_author_address ; Solid State and Structural Chemistry Unit Indian Institute of Science C.V. Raman Avenue Bangalore 560 012 INDIA ; _publ_contact_author_email SNATARAJAN@SSCU.IISC.ERNET.IN _publ_section_title ; The role of temperature on the structure and dimensionality of MOFs: An illustrative study of the formation of Manganese Oxy-bis(benzoate) structures ; loop_ _publ_author_name 'Srinivasan Natarajan' 'Partha Mahata' 'A. Sundaresan' #=============================================================================== data_compound(III) _database_code_depnum_ccdc_archive 'CCDC 637649' #=============================================================================== _chemical_name_systematic ; ? ; _chemical_name_common 'Manganese carboxylate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 Mn2 N0 O7' _chemical_formula_weight 400.1 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 29.135(8) _cell_length_b 7.461(2) _cell_length_c 6.1111(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1328.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1582 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 27.97 _exptl_crystal_description 'Plate like' _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.001 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 1.938 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7731 _exptl_absorpt_correction_T_max 0.8449 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _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 'Bruker SMART CCD area dtector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10371 _diffrn_reflns_av_R_equivalents 0.0687 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 27.97 _reflns_number_total 1582 _reflns_number_gt 1227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction SAINT _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0224P)^2^+6.7647P] 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 1582 _refine_ls_number_parameters 109 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1183 _refine_ls_goodness_of_fit_ref 1.292 _refine_ls_restrained_S_all 1.292 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.50255(3) 0.15595(9) 0.18421(11) 0.0138(2) Uani 1 1 d . . . O1 O 0.52474(11) -0.1172(4) 0.1445(5) 0.0128(7) Uani 1 1 d D . . O2 O 0.43379(12) 0.0563(5) 0.2840(6) 0.0222(9) Uani 1 1 d . . . O3 O 0.45186(11) -0.1607(5) 0.5190(5) 0.0156(7) Uani 1 1 d . . . O4 O 0.2500 0.0000 0.8405(9) 0.0281(13) Uani 1 2 d S . . C1 C 0.37872(17) -0.0182(6) 0.5511(8) 0.0156(11) Uani 1 1 d . . . C2 C 0.34364(18) 0.0734(7) 0.4452(9) 0.0210(11) Uani 1 1 d . . . H2 H 0.3496 0.1312 0.3134 0.025 Uiso 1 1 calc R . . C3 C 0.29988(18) 0.0797(8) 0.5335(10) 0.0249(12) Uani 1 1 d . . . H3 H 0.2764 0.1391 0.4605 0.030 Uiso 1 1 calc R . . C4 C 0.29163(17) -0.0046(7) 0.7339(9) 0.0169(11) Uani 1 1 d . . . C5 C 0.32661(18) -0.0869(7) 0.8448(9) 0.0223(11) Uani 1 1 d . . . H5 H 0.3211 -0.1384 0.9809 0.027 Uiso 1 1 calc R . . C6 C 0.36971(17) -0.0933(7) 0.7548(9) 0.0189(11) Uani 1 1 d . . . H6 H 0.3933 -0.1489 0.8315 0.023 Uiso 1 1 calc R . . C7 C 0.42441(17) -0.0391(6) 0.4460(8) 0.0138(10) Uani 1 1 d . . . H10 H 0.5568(5) -0.138(7) 0.144(9) 0.021(15) 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 0.0185(4) 0.0122(3) 0.0108(3) -0.0009(3) -0.0001(3) -0.0001(3) O1 0.0176(17) 0.0082(16) 0.0126(17) -0.0006(13) 0.0000(13) -0.0005(13) O2 0.024(2) 0.020(2) 0.022(2) 0.0102(16) 0.0036(16) -0.0008(15) O3 0.0178(17) 0.0148(17) 0.0142(17) -0.0024(15) -0.0013(14) 0.0055(15) O4 0.013(3) 0.051(4) 0.021(3) 0.000 0.000 0.003(2) C1 0.014(2) 0.013(2) 0.020(3) 0.002(2) -0.001(2) -0.004(2) C2 0.023(3) 0.019(3) 0.022(3) 0.006(2) -0.001(2) 0.000(2) C3 0.018(3) 0.026(3) 0.031(3) 0.008(3) -0.004(2) 0.008(2) C4 0.012(3) 0.017(3) 0.022(3) -0.004(2) 0.000(2) -0.001(2) C5 0.024(3) 0.024(3) 0.019(3) 0.004(2) 0.000(2) 0.001(2) C6 0.014(2) 0.021(3) 0.022(3) 0.003(2) -0.002(2) 0.004(2) C7 0.015(2) 0.006(2) 0.020(3) -0.0045(19) -0.003(2) -0.0016(19) _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 2.143(3) 4_655 ? Mn1 O1 2.151(3) . ? Mn1 O1 2.180(3) 5_655 ? Mn1 O2 2.222(4) . ? Mn1 O3 2.248(3) 5_656 ? Mn1 O3 2.275(3) 4_655 ? O1 Mn1 2.143(3) 4_645 ? O1 Mn1 2.180(3) 5_655 ? O1 H10 0.947(10) . ? O2 C7 1.250(6) . ? O3 C7 1.289(6) . ? O3 Mn1 2.248(3) 5_656 ? O3 Mn1 2.275(3) 4_645 ? O4 C4 1.377(6) 2 ? O4 C4 1.377(6) . ? C1 C2 1.389(7) . ? C1 C6 1.390(7) . ? C1 C7 1.486(7) . ? C2 C3 1.385(7) . ? C2 H2 0.9300 . ? C3 C4 1.398(8) . ? C3 H3 0.9300 . ? C4 C5 1.369(7) . ? C5 C6 1.372(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? 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 156.15(7) 4_655 . ? O1 Mn1 O1 114.80(13) 4_655 5_655 ? O1 Mn1 O1 83.11(13) . 5_655 ? O1 Mn1 O2 78.22(13) 4_655 . ? O1 Mn1 O2 89.13(13) . . ? O1 Mn1 O2 83.08(13) 5_655 . ? O1 Mn1 O3 79.21(12) 4_655 5_656 ? O1 Mn1 O3 85.89(12) . 5_656 ? O1 Mn1 O3 163.96(12) 5_655 5_656 ? O2 Mn1 O3 108.45(13) . 5_656 ? O1 Mn1 O3 90.47(13) 4_655 4_655 ? O1 Mn1 O3 109.43(13) . 4_655 ? O1 Mn1 O3 77.87(12) 5_655 4_655 ? O2 Mn1 O3 151.29(13) . 4_655 ? O3 Mn1 O3 94.94(12) 5_656 4_655 ? Mn1 O1 Mn1 125.56(16) 4_645 . ? Mn1 O1 Mn1 102.11(13) 4_645 5_655 ? Mn1 O1 Mn1 96.89(13) . 5_655 ? Mn1 O1 H10 104(3) 4_645 . ? Mn1 O1 H10 117(3) . . ? Mn1 O1 H10 110(3) 5_655 . ? C7 O2 Mn1 127.2(3) . . ? C7 O3 Mn1 129.4(3) . 5_656 ? C7 O3 Mn1 126.6(3) . 4_645 ? Mn1 O3 Mn1 96.03(12) 5_656 4_645 ? C4 O4 C4 123.5(6) 2 . ? C2 C1 C6 118.5(5) . . ? C2 C1 C7 120.6(4) . . ? C6 C1 C7 120.9(5) . . ? C3 C2 C1 120.8(5) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 119.0(5) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 O4 115.6(5) . . ? C5 C4 C3 120.5(5) . . ? O4 C4 C3 123.7(5) . . ? C4 C5 C6 119.9(5) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 121.2(5) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? O2 C7 O3 122.6(5) . . ? O2 C7 C1 118.6(4) . . ? O3 C7 C1 118.7(4) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.681 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.126 #=============================================================================== # Attachment 'CIF.txt' data_compound(I) _database_code_depnum_ccdc_archive 'CCDC 648374' #=============================================================================== _chemical_name_systematic ; ? ; _chemical_name_common 'Manganese carboxylate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Mn N0 O9' _chemical_formula_weight 381.19 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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 16.902(6) _cell_length_b 10.506(4) _cell_length_c 9.062(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.524(5) _cell_angle_gamma 90.00 _cell_volume 1604.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3760 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 28.03 _exptl_crystal_description 'Block type' _exptl_crystal_colour 'Pale brown' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 0.868 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9030 _exptl_absorpt_correction_T_max 0.9182 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13544 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 28.03 _reflns_number_total 3760 _reflns_number_gt 3302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction SAINT _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0538P)^2^+2.3088P] 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 0.0226(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3760 _refine_ls_number_parameters 242 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.38752(2) 0.16805(3) 0.48515(4) 0.02361(14) Uani 1 1 d . . . O1 O 0.29236(10) 0.11953(18) 0.61427(19) 0.0310(4) Uani 1 1 d . . . O2 O 0.31965(11) 0.2549(2) 0.7980(2) 0.0393(5) Uani 1 1 d . . . O3 O -0.38314(10) 0.01681(17) 0.6211(2) 0.0332(4) Uani 1 1 d . . . O4 O 0.49544(10) 0.19729(18) 0.3702(2) 0.0318(4) Uani 1 1 d D . . O5 O 0.40675(14) 0.3654(2) 0.5669(2) 0.0434(5) Uani 1 1 d D . . O6 O 0.47018(10) 0.09532(17) 0.67330(19) 0.0286(4) Uani 1 1 d D . . O7 O -0.35883(13) 0.2008(2) 0.5142(3) 0.0579(7) Uani 1 1 d . . . O8 O -0.03665(11) 0.1240(3) 0.9084(2) 0.0578(7) Uani 1 1 d . . . O100 O 0.3864(4) 0.5615(3) 0.3709(5) 0.171(3) Uani 1 1 d . . . C1 C 0.19005(14) 0.1656(2) 0.7689(3) 0.0265(5) Uani 1 1 d . . . C2 C 0.15997(15) 0.2521(3) 0.8667(3) 0.0348(6) Uani 1 1 d . . . H2 H 0.1917 0.3182 0.9056 0.042 Uiso 1 1 calc R . . C3 C 0.08252(16) 0.2395(3) 0.9062(3) 0.0422(7) Uani 1 1 d . . . H3 H 0.0621 0.2979 0.9703 0.051 Uiso 1 1 calc R . . C4 C 0.03620(15) 0.1401(3) 0.8501(3) 0.0386(7) Uani 1 1 d . . . C5 C 0.06436(16) 0.0545(3) 0.7525(3) 0.0399(7) Uani 1 1 d . . . H5 H 0.0322 -0.0115 0.7144 0.048 Uiso 1 1 calc R . . C6 C 0.14169(15) 0.0675(3) 0.7112(3) 0.0332(6) Uani 1 1 d . . . H6 H 0.1611 0.0103 0.6446 0.040 Uiso 1 1 calc R . . C7 C 0.27333(13) 0.1810(2) 0.7253(3) 0.0244(5) Uani 1 1 d . . . C8 C -0.10623(14) 0.1159(3) 0.8178(3) 0.0358(6) Uani 1 1 d . . . C9 C -0.11987(17) 0.1839(3) 0.6887(4) 0.0457(8) Uani 1 1 d . . . H9 H -0.0794 0.2309 0.6511 0.055 Uiso 1 1 calc R . . C10 C -0.19529(17) 0.1809(3) 0.6152(4) 0.0431(7) Uani 1 1 d . . . H10 H -0.2054 0.2275 0.5285 0.052 Uiso 1 1 calc R . . C11 C -0.25562(14) 0.1095(2) 0.6694(3) 0.0298(5) Uani 1 1 d . . . C12 C -0.23908(15) 0.0400(3) 0.7979(3) 0.0371(6) Uani 1 1 d . . . H12 H -0.2786 -0.0101 0.8340 0.044 Uiso 1 1 calc R . . C13 C -0.16493(16) 0.0436(3) 0.8734(3) 0.0389(6) Uani 1 1 d . . . H13 H -0.1548 -0.0022 0.9606 0.047 Uiso 1 1 calc R . . C14 C -0.33762(15) 0.1100(3) 0.5944(3) 0.0331(6) Uani 1 1 d . . . H51 H 0.390(3) 0.378(6) 0.663(3) 0.117(19) Uiso 1 1 d D . . H52 H 0.395(3) 0.437(3) 0.506(4) 0.095(16) Uiso 1 1 d D . . H41 H 0.5466(11) 0.189(4) 0.418(4) 0.065(12) Uiso 1 1 d D . . H42 H 0.493(2) 0.267(2) 0.305(3) 0.055(10) Uiso 1 1 d D . . H61 H 0.444(2) 0.033(3) 0.725(4) 0.066(12) Uiso 1 1 d D . . H62 H 0.5194(12) 0.058(3) 0.657(4) 0.058(11) 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 0.0176(2) 0.0271(2) 0.0262(2) 0.00186(13) 0.00175(13) 0.00125(13) O1 0.0230(9) 0.0395(10) 0.0312(9) -0.0068(7) 0.0073(7) -0.0051(7) O2 0.0222(9) 0.0575(13) 0.0380(10) -0.0146(9) 0.0016(7) -0.0114(8) O3 0.0182(8) 0.0335(9) 0.0477(11) -0.0113(8) 0.0017(7) -0.0022(7) O4 0.0205(9) 0.0390(10) 0.0359(10) 0.0086(8) 0.0029(7) 0.0002(7) O5 0.0611(14) 0.0328(10) 0.0375(11) -0.0002(9) 0.0118(10) 0.0026(10) O6 0.0230(8) 0.0308(9) 0.0320(9) -0.0003(7) 0.0023(7) 0.0047(7) O7 0.0343(12) 0.0485(13) 0.0863(18) 0.0195(12) -0.0242(11) -0.0052(10) O8 0.0168(9) 0.125(2) 0.0314(10) 0.0005(12) 0.0016(8) -0.0141(11) O100 0.382(8) 0.0433(17) 0.106(3) 0.0235(18) 0.138(4) 0.048(3) C1 0.0194(11) 0.0360(13) 0.0240(11) 0.0012(9) 0.0012(8) -0.0019(9) C2 0.0228(12) 0.0446(15) 0.0373(14) -0.0094(11) 0.0035(10) -0.0023(11) C3 0.0227(13) 0.0648(19) 0.0397(15) -0.0122(14) 0.0053(11) 0.0015(13) C4 0.0164(11) 0.0705(19) 0.0286(13) 0.0046(13) 0.0006(9) -0.0048(12) C5 0.0264(13) 0.0559(17) 0.0368(14) -0.0026(13) -0.0003(11) -0.0173(12) C6 0.0256(12) 0.0428(14) 0.0315(13) -0.0058(11) 0.0033(10) -0.0077(11) C7 0.0175(10) 0.0316(12) 0.0236(11) 0.0013(9) -0.0016(8) -0.0018(9) C8 0.0161(11) 0.0575(17) 0.0334(13) -0.0064(12) 0.0005(9) -0.0033(11) C9 0.0232(13) 0.064(2) 0.0495(17) 0.0106(14) 0.0005(12) -0.0167(13) C10 0.0289(14) 0.0503(17) 0.0485(17) 0.0141(13) -0.0070(12) -0.0108(12) C11 0.0177(11) 0.0289(12) 0.0423(14) -0.0030(10) -0.0004(10) -0.0013(9) C12 0.0225(12) 0.0471(16) 0.0413(15) 0.0047(12) 0.0006(10) -0.0101(11) C13 0.0263(13) 0.0547(17) 0.0353(14) 0.0069(12) -0.0010(10) -0.0041(12) C14 0.0206(12) 0.0326(13) 0.0448(15) -0.0064(11) -0.0053(10) 0.0005(10) _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 2.1244(17) . ? Mn1 O2 2.1306(19) 4_565 ? Mn1 O3 2.1666(19) 3_556 ? Mn1 O4 2.1925(19) . ? Mn1 O5 2.218(2) . ? Mn1 O6 2.2511(18) . ? O1 C7 1.258(3) . ? O2 C7 1.253(3) . ? O2 Mn1 2.1306(19) 4_566 ? O3 C14 1.280(3) . ? O3 Mn1 2.1666(19) 3_556 ? O7 C14 1.235(4) . ? O8 C8 1.383(3) . ? O8 C4 1.388(3) . ? C1 C6 1.392(4) . ? C1 C2 1.393(4) . ? C1 C7 1.501(3) . ? C2 C3 1.390(4) . ? C3 C4 1.378(4) . ? C4 C5 1.373(4) . ? C5 C6 1.394(4) . ? C8 C9 1.375(4) . ? C8 C13 1.376(4) . ? C9 C10 1.391(4) . ? C10 C11 1.386(4) . ? C11 C12 1.385(4) . ? C11 C14 1.495(3) . ? C12 C13 1.380(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 O1 Mn1 O2 98.40(8) . 4_565 ? O1 Mn1 O3 91.66(7) . 3_556 ? O2 Mn1 O3 89.38(8) 4_565 3_556 ? O1 Mn1 O4 171.81(7) . . ? O2 Mn1 O4 89.11(7) 4_565 . ? O3 Mn1 O4 85.11(7) 3_556 . ? O1 Mn1 O5 97.92(8) . . ? O2 Mn1 O5 88.08(9) 4_565 . ? O3 Mn1 O5 170.35(8) 3_556 . ? O4 Mn1 O5 85.54(8) . . ? O1 Mn1 O6 87.31(7) . . ? O2 Mn1 O6 174.16(7) 4_565 . ? O3 Mn1 O6 91.71(7) 3_556 . ? O4 Mn1 O6 85.27(7) . . ? O5 Mn1 O6 89.91(8) . . ? C7 O1 Mn1 124.72(16) . . ? C7 O2 Mn1 158.30(19) . 4_566 ? C14 O3 Mn1 126.98(17) . 3_556 ? C8 O8 C4 121.3(2) . . ? C6 C1 C2 119.3(2) . . ? C6 C1 C7 121.1(2) . . ? C2 C1 C7 119.6(2) . . ? C3 C2 C1 120.0(3) . . ? C4 C3 C2 119.7(3) . . ? C5 C4 C3 121.2(2) . . ? C5 C4 O8 121.9(3) . . ? C3 C4 O8 116.6(3) . . ? C4 C5 C6 119.2(3) . . ? C1 C6 C5 120.5(3) . . ? O2 C7 O1 123.4(2) . . ? O2 C7 C1 119.2(2) . . ? O1 C7 C1 117.4(2) . . ? C9 C8 C13 121.4(2) . . ? C9 C8 O8 123.5(3) . . ? C13 C8 O8 114.9(3) . . ? C8 C9 C10 118.8(3) . . ? C11 C10 C9 120.9(3) . . ? C12 C11 C10 118.6(2) . . ? C12 C11 C14 120.2(2) . . ? C10 C11 C14 121.2(2) . . ? C13 C12 C11 121.1(2) . . ? C8 C13 C12 119.1(3) . . ? O7 C14 O3 123.4(2) . . ? O7 C14 C11 119.1(2) . . ? O3 C14 C11 117.4(2) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.03 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 1.377 _refine_diff_density_min -1.278 _refine_diff_density_rms 0.073 #=============================================================================== data_compound(II) _database_code_depnum_ccdc_archive 'CCDC 648375' #=============================================================================== _chemical_name_systematic ; ? ; _chemical_name_common 'Manganese carboxylate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 Mn1 N0 O6' _chemical_formula_weight 329.16 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 14.399(3) _cell_length_b 6.3626(15) _cell_length_c 7.3555(18) _cell_angle_alpha 90.00 _cell_angle_beta 102.867(4) _cell_angle_gamma 90.00 _cell_volume 657.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1558 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 28.02 _exptl_crystal_description 'Plate like' _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 334 _exptl_absorpt_coefficient_mu 1.030 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9040 _exptl_absorpt_correction_T_max 0.9222 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _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 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5530 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 28.02 _reflns_number_total 1558 _reflns_number_gt 1269 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction SAINT _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0414P)^2^+0.0115P] 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 1558 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.5000 0.68325(7) 0.7500 0.02915(17) Uani 1 2 d S . . O1 O 0.36960(11) 0.4256(3) 1.0991(2) 0.0507(5) Uani 1 1 d . . . O2 O 0.5000 1.0118(4) 0.7500 0.0571(8) Uani 1 2 d S . . O3 O 0.43534(10) 0.6986(2) 0.9909(2) 0.0357(4) Uani 1 1 d . . . O4 O 0.0000 0.9579(3) 0.7500 0.0424(6) Uani 1 2 d S . . C1 C 0.26591(14) 0.6860(3) 0.9410(3) 0.0287(5) Uani 1 1 d . . . C2 C 0.25462(15) 0.8817(3) 0.8551(3) 0.0334(5) Uani 1 1 d . . . H2 H 0.3081 0.9570 0.8418 0.040 Uiso 1 1 calc R . . C3 C 0.16547(15) 0.9654(3) 0.7898(3) 0.0350(5) Uani 1 1 d . . . H3 H 0.1587 1.0968 0.7331 0.042 Uiso 1 1 calc R . . C4 C 0.08597(14) 0.8540(3) 0.8086(3) 0.0322(5) Uani 1 1 d . . . C5 C 0.09508(16) 0.6593(3) 0.8941(3) 0.0371(5) Uani 1 1 d . . . H5 H 0.0413 0.5852 0.9075 0.044 Uiso 1 1 calc R . . C6 C 0.18515(15) 0.5761(4) 0.9597(3) 0.0341(5) Uani 1 1 d . . . H6 H 0.1917 0.4450 1.0170 0.041 Uiso 1 1 calc R . . C7 C 0.36277(15) 0.5961(4) 1.0137(3) 0.0317(5) Uani 1 1 d . . . H2A H 0.519(2) 1.092(4) 0.835(4) 0.061(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0221(3) 0.0271(2) 0.0373(3) 0.000 0.00467(19) 0.000 O1 0.0312(9) 0.0631(11) 0.0582(11) 0.0326(9) 0.0110(8) 0.0138(8) O2 0.093(2) 0.0270(13) 0.0423(17) 0.000 -0.0037(16) 0.000 O3 0.0227(8) 0.0449(9) 0.0381(9) -0.0087(7) 0.0040(7) -0.0019(7) O4 0.0204(11) 0.0390(12) 0.0604(16) 0.000 -0.0065(10) 0.000 C1 0.0237(10) 0.0359(11) 0.0253(11) 0.0013(9) 0.0032(8) 0.0015(9) C2 0.0209(11) 0.0388(12) 0.0397(13) 0.0043(10) 0.0047(9) -0.0039(9) C3 0.0303(12) 0.0332(11) 0.0388(13) 0.0077(10) 0.0021(10) -0.0009(9) C4 0.0195(10) 0.0391(12) 0.0343(12) -0.0012(9) -0.0017(9) 0.0026(9) C5 0.0239(11) 0.0443(13) 0.0414(13) 0.0057(10) 0.0039(10) -0.0078(10) C6 0.0307(12) 0.0358(12) 0.0339(13) 0.0069(10) 0.0033(9) -0.0015(10) C7 0.0278(12) 0.0445(12) 0.0221(11) -0.0013(9) 0.0040(9) 0.0049(10) _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 2.0760(16) 4_565 ? Mn1 O1 2.0760(16) 3_667 ? Mn1 O2 2.091(3) . ? Mn1 O3 2.1799(15) . ? Mn1 O3 2.1799(15) 2_656 ? O1 C7 1.246(3) . ? O1 Mn1 2.0760(16) 3_667 ? O3 C7 1.274(3) . ? O4 C4 1.385(2) 2_556 ? O4 C4 1.385(2) . ? C1 C2 1.389(3) . ? C1 C6 1.390(3) . ? C1 C7 1.492(3) . ? C2 C3 1.374(3) . ? C3 C4 1.379(3) . ? C4 C5 1.382(3) . ? C5 C6 1.384(3) . ? 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 141.03(11) 4_565 3_667 ? O1 Mn1 O2 109.49(6) 4_565 . ? O1 Mn1 O2 109.49(6) 3_667 . ? O1 Mn1 O3 87.17(6) 4_565 . ? O1 Mn1 O3 94.55(6) 3_667 . ? O2 Mn1 O3 87.43(4) . . ? O1 Mn1 O3 94.55(6) 4_565 2_656 ? O1 Mn1 O3 87.17(6) 3_667 2_656 ? O2 Mn1 O3 87.43(4) . 2_656 ? O3 Mn1 O3 174.85(8) . 2_656 ? C7 O1 Mn1 121.35(15) . 3_667 ? C7 O3 Mn1 126.52(13) . . ? C4 O4 C4 123.0(2) 2_556 . ? C2 C1 C6 118.69(19) . . ? C2 C1 C7 120.80(19) . . ? C6 C1 C7 120.51(19) . . ? C3 C2 C1 120.80(19) . . ? C2 C3 C4 119.8(2) . . ? C3 C4 C5 120.62(19) . . ? C3 C4 O4 115.32(19) . . ? C5 C4 O4 123.9(2) . . ? C4 C5 C6 119.2(2) . . ? C5 C6 C1 120.9(2) . . ? O1 C7 O3 122.5(2) . . ? O1 C7 C1 118.5(2) . . ? O3 C7 C1 119.02(19) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 28.02 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.314 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.061