# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Py _audit_creation_date 2012-09-13T14:52:08-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Bis(benzoylacetonato)bis(pyridine)manganese(II) ; _chemical_formula_sum 'C30 H28 Mn N2 O4' _chemical_formula_moiety 'C30 H28 Mn N2 O4' _chemical_formula_weight 535.48 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.6425(7) _cell_length_b 17.5482(9) _cell_length_c 11.5193(8) _cell_angle_alpha 90 _cell_angle_beta 141.110(3) _cell_angle_gamma 90 _cell_volume 1350.65(17) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2407 _cell_measurement_theta_min 3.8193 _cell_measurement_theta_max 39.7072 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 558 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.526 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_unetI/netI 0.0464 _diffrn_reflns_number 6161 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.96 _diffrn_reflns_theta_max 27 _diffrn_reflns_theta_full 27 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _reflns_number_total 2906 _reflns_number_gt 1857 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_cell_refinement ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_data_reduction ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_structure_solution ; 'SIR-92 (Altomare, Cascanaro, Giacovazzo, Gualardi, 1993)' ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ; WinGX (Farrugia, 1999) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0473P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2906 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.058 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0834 _refine_ls_wR_factor_gt 0.079 _refine_ls_goodness_of_fit_ref 0.844 _refine_ls_restrained_S_all 0.844 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.278 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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_ _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 0 0 0.04636(14) Uani 1 2 d S . . O2 O 0.04929(18) -0.05613(7) 0.19539(15) 0.0533(3) Uani 1 1 d . . . C12 C 0.6231(3) -0.09702(13) 0.4150(3) 0.0656(6) Uani 1 1 d . . . H12 H 0.7222 -0.1074 0.5407 0.079 Uiso 1 1 calc R . . C10 C 0.0294(3) -0.21599(11) 0.3726(2) 0.0494(5) Uani 1 1 d . . . H10 H -0.0319 -0.2521 0.2813 0.059 Uiso 1 1 calc R . . C14 C 0.5094(3) -0.09144(14) 0.1407(3) 0.0717(7) Uani 1 1 d . . . H14 H 0.5298 -0.0977 0.0761 0.086 Uiso 1 1 calc R . . C8 C 0.2018(3) -0.18522(14) 0.6714(3) 0.0670(6) Uani 1 1 d . . . H8 H 0.2579 -0.2001 0.782 0.08 Uiso 1 1 calc R . . C11 C 0.4404(3) -0.07055(12) 0.3180(2) 0.0580(5) Uani 1 1 d . . . H11 H 0.4182 -0.0632 0.381 0.07 Uiso 1 1 calc R . . C15 C 0.3301(3) -0.06548(13) 0.0530(3) 0.0622(6) Uani 1 1 d . . . H15 H 0.2294 -0.0548 -0.0727 0.075 Uiso 1 1 calc R . . C7 C 0.2070(3) -0.11013(14) 0.6425(3) 0.0683(6) Uani 1 1 d . . . H7 H 0.2658 -0.0742 0.7334 0.082 Uiso 1 1 calc R . . C6 C 0.1256(3) -0.08759(12) 0.4797(2) 0.0548(5) Uani 1 1 d . . . H6 H 0.1317 -0.0367 0.462 0.066 Uiso 1 1 calc R . . C5 C 0.0347(2) -0.14030(10) 0.3418(2) 0.0412(4) Uani 1 1 d . . . N1 N 0.2917(2) -0.05462(9) 0.13740(19) 0.0522(4) Uani 1 1 d . . . C9 C 0.1146(3) -0.23827(12) 0.5381(2) 0.0586(5) Uani 1 1 d . . . H9 H 0.1124 -0.2893 0.5585 0.07 Uiso 1 1 calc R . . C13 C 0.6582(3) -0.10802(14) 0.3250(3) 0.0689(6) Uani 1 1 d . . . H13 H 0.7811 -0.1265 0.3878 0.083 Uiso 1 1 calc R . . C4 C -0.0407(2) -0.11406(10) 0.1715(2) 0.0419(4) Uani 1 1 d . . . C2 C -0.2624(2) -0.14187(10) -0.1564(2) 0.0439(4) Uani 1 1 d . . . C3 C -0.1965(2) -0.15260(10) 0.0061(2) 0.0468(4) Uani 1 1 d . . . H3 H -0.2638 -0.1889 0.0019 0.056 Uiso 1 1 calc R . . O1 O -0.18717(18) -0.09572(7) -0.17341(15) 0.0517(3) Uani 1 1 d . . . C1 C -0.4299(3) -0.19108(12) -0.3207(2) 0.0605(6) Uani 1 1 d . . . H1A H -0.5368 -0.1594 -0.4254 0.091 Uiso 1 1 calc R . . H1B H -0.4783 -0.2227 -0.2936 0.091 Uiso 1 1 calc R . . H1C H -0.3819 -0.2226 -0.3484 0.091 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0545(2) 0.0449(2) 0.0460(2) 0.00187(18) 0.0407(2) -0.00385(19) O2 0.0605(8) 0.0552(8) 0.0459(7) -0.0019(6) 0.0418(7) -0.0137(7) C12 0.0552(13) 0.0756(15) 0.0469(11) 0.0001(10) 0.0348(11) -0.0013(11) C10 0.0434(10) 0.0530(12) 0.0491(10) 0.0018(9) 0.0353(9) -0.0054(8) C14 0.0737(15) 0.0905(18) 0.0641(13) -0.0016(12) 0.0569(13) 0.0094(12) C8 0.0629(13) 0.0883(17) 0.0495(11) 0.0129(12) 0.0437(11) -0.0022(12) C11 0.0626(13) 0.0659(14) 0.0509(11) 0.0005(10) 0.0455(11) -0.0004(10) C15 0.0646(13) 0.0729(14) 0.0492(10) 0.0043(10) 0.0443(11) 0.0096(11) C7 0.0810(15) 0.0752(16) 0.0526(11) -0.0067(10) 0.0529(12) -0.0123(12) C6 0.0668(13) 0.0515(12) 0.0547(11) 0.0008(9) 0.0494(11) -0.0053(9) C5 0.0376(9) 0.0481(11) 0.0430(9) 0.0033(8) 0.0326(8) -0.0003(8) N1 0.0595(9) 0.0520(10) 0.0496(8) 0.0009(7) 0.0435(8) 0.0004(8) C9 0.0531(12) 0.0598(13) 0.0612(12) 0.0149(11) 0.0440(11) -0.0024(10) C13 0.0586(13) 0.0762(16) 0.0678(13) -0.0030(11) 0.0482(12) 0.0041(11) C4 0.0423(9) 0.0446(10) 0.0462(9) 0.0049(8) 0.0363(9) 0.0036(8) C2 0.0403(9) 0.0434(10) 0.0447(9) 0.0015(8) 0.0322(9) 0.0041(8) C3 0.0435(10) 0.0523(11) 0.0457(9) 0.0003(8) 0.0350(9) -0.0050(8) O1 0.0593(8) 0.0527(8) 0.0456(7) -0.0043(6) 0.0415(7) -0.0075(6) C1 0.0493(11) 0.0679(14) 0.0460(10) -0.0059(10) 0.0325(10) -0.0089(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.1150(11) 3 ? Mn1 O2 2.1150(11) . ? Mn1 O1 2.1413(12) . ? Mn1 O1 2.1413(12) 3 ? Mn1 N1 2.3262(16) . ? Mn1 N1 2.3262(16) 3 ? O2 C4 1.271(2) . ? C12 C13 1.362(3) . ? C12 C11 1.365(3) . ? C12 H12 0.93 . ? C10 C9 1.385(2) . ? C10 C5 1.387(2) . ? C10 H10 0.93 . ? C14 C13 1.366(3) . ? C14 C15 1.367(3) . ? C14 H14 0.93 . ? C8 C9 1.366(3) . ? C8 C7 1.371(3) . ? C8 H8 0.93 . ? C11 N1 1.336(2) . ? C11 H11 0.93 . ? C15 N1 1.329(5) . ? C15 H15 0.93 . ? C7 C6 1.377(3) . ? C7 H7 0.93 . ? C6 C5 1.386(2) . ? C6 H6 0.93 . ? C5 C4 1.502(2) . ? C9 H9 0.93 . ? C13 H13 0.93 . ? C4 C3 1.385(2) . ? C2 O1 1.257(2) . ? C2 C3 1.410(2) . ? C2 C1 1.502(2) . ? C3 H3 0.93 . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? 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 180 3 . ? O2 Mn1 O1 95.31(4) 3 . ? O2 Mn1 O1 84.69(4) . . ? O2 Mn1 O1 84.69(4) 3 3 ? O2 Mn1 O1 95.31(4) . 3 ? O1 Mn1 O1 180 . 3 ? O2 Mn1 N1 90.59(5) 3 . ? O2 Mn1 N1 89.41(5) . . ? O1 Mn1 N1 95.24(5) . . ? O1 Mn1 N1 84.76(5) 3 . ? O2 Mn1 N1 89.41(5) 3 3 ? O2 Mn1 N1 90.59(5) . 3 ? O1 Mn1 N1 84.76(5) . 3 ? O1 Mn1 N1 95.24(5) 3 3 ? N1 Mn1 N1 180 . 3 ? C4 O2 Mn1 128.39(11) . . ? C13 C12 C11 119.07(18) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C9 C10 C5 120.58(18) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? C13 C14 C15 118.9(2) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C9 C8 C7 120.22(18) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? N1 C11 C12 123.46(19) . . ? N1 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? N1 C15 C14 123.65(18) . . ? N1 C15 H15 118.2 . . ? C14 C15 H15 118.2 . . ? C8 C7 C6 120.3(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C6 C5 120.45(19) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C5 C10 118.51(16) . . ? C6 C5 C4 118.60(16) . . ? C10 C5 C4 122.74(16) . . ? C15 N1 C11 116.30(17) . . ? C15 N1 Mn1 124.65(12) . . ? C11 N1 Mn1 118.79(13) . . ? C8 C9 C10 119.89(19) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C12 C13 C14 118.6(2) . . ? C12 C13 H13 120.7 . . ? C14 C13 H13 120.7 . . ? O2 C4 C3 125.58(15) . . ? O2 C4 C5 114.58(14) . . ? C3 C4 C5 119.83(16) . . ? O1 C2 C3 125.06(16) . . ? O1 C2 C1 116.70(15) . . ? C3 C2 C1 118.20(17) . . ? C4 C3 C2 125.92(17) . . ? C4 C3 H3 117 . . ? C2 C3 H3 117 . . ? C2 O1 Mn1 127.07(11) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _database_code_depnum_ccdc_archive 'CCDC 938354' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4MePy _audit_creation_date 2012-09-18T15:56:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Bis(benzoylacetonato)bis(pyridine)manganese(II) ; _chemical_formula_sum 'C32 H32 Mn N2 O4' _chemical_formula_moiety 'C32 H32 Mn N2 O4' _chemical_formula_weight 563.54 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5507(19) _cell_length_b 17.045(3) _cell_length_c 9.6962(18) _cell_angle_alpha 90 _cell_angle_beta 110.425(18) _cell_angle_gamma 90 _cell_volume 1479.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 590 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.484 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_unetI/netI 0.0464 _diffrn_reflns_number 6825 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.43 _diffrn_reflns_theta_max 27 _diffrn_reflns_theta_full 27 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 3176 _reflns_number_gt 2427 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_cell_refinement ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_data_reduction ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_structure_solution ; 'SIR-92 (Altomare, Cascanaro, Giacovazzo, Gualardi, 1993)' ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ; WinGX (Farrugia, 1999) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0958P)^2^+1.1137P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3176 _refine_ls_number_parameters 180 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.2106 _refine_ls_wR_factor_gt 0.1943 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.173 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.776 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.067 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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_ _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 0.5 0.5 0.0435(3) Uani 1 2 d S . . O2 O -0.0857(3) 0.54871(16) 0.6557(3) 0.0468(6) Uani 1 1 d . . . C4 C -0.2142(4) 0.5747(2) 0.6385(4) 0.0397(8) Uani 1 1 d . . . N1 N 0.0831(4) 0.6235(2) 0.4557(5) 0.0674(8) Uani 1 1 d U . . C5 C -0.2375(4) 0.6023(2) 0.7744(4) 0.0436(8) Uani 1 1 d . . . C6 C -0.1676(5) 0.5615(2) 0.9041(4) 0.0509(9) Uani 1 1 d . . . H6 H -0.1108 0.5174 0.9029 0.061 Uiso 1 1 calc R . . C8 C -0.2607(7) 0.6519(3) 1.0379(6) 0.0777(15) Uani 1 1 d . . . H8 H -0.2674 0.6689 1.1265 0.093 Uiso 1 1 calc R . . C10 C -0.3211(5) 0.6682(3) 0.7784(5) 0.0618(11) Uani 1 1 d . . . H10 H -0.3707 0.6957 0.6923 0.074 Uiso 1 1 calc R . . C7 C -0.1808(6) 0.5854(3) 1.0339(5) 0.0673(12) Uani 1 1 d . . . H7 H -0.1357 0.5565 1.1193 0.081 Uiso 1 1 calc R . . C9 C -0.3306(6) 0.6931(3) 0.9105(7) 0.0809(16) Uani 1 1 d . . . H9 H -0.3847 0.738 0.9133 0.097 Uiso 1 1 calc R . . C15 C 0.0230(6) 0.6887(3) 0.4775(6) 0.0750(9) Uani 1 1 d U . . H15 H -0.0589 0.6852 0.508 0.09 Uiso 1 1 calc R . . C3 C -0.3333(4) 0.5765(2) 0.5061(4) 0.0469(9) Uani 1 1 d . . . H3 H -0.4228 0.5974 0.5072 0.056 Uiso 1 1 calc R . . C13 C 0.1872(6) 0.7722(3) 0.4094(7) 0.0768(9) Uani 1 1 d U . . C16 C 0.2413(6) 0.8523(3) 0.3839(8) 0.0909(18) Uani 1 1 d . . . H16A H 0.1716 0.8746 0.2957 0.136 Uiso 1 1 calc R . . H16B H 0.3374 0.8475 0.3738 0.136 Uiso 1 1 calc R . . H16C H 0.2493 0.8858 0.466 0.136 Uiso 1 1 calc R . . C11 C 0.1957(6) 0.6318(3) 0.4095(7) 0.0769(9) Uani 1 1 d U . . H11 H 0.2423 0.5869 0.3923 0.092 Uiso 1 1 calc R . . C14 C 0.0720(6) 0.7620(3) 0.4586(7) 0.0794(10) Uani 1 1 d U . . H14 H 0.0251 0.8057 0.48 0.095 Uiso 1 1 calc R . . C12 C 0.2488(6) 0.7035(3) 0.3850(7) 0.0797(9) Uani 1 1 d U . . H12 H 0.3285 0.7054 0.351 0.096 Uiso 1 1 calc R . . C2 C -0.3301(4) 0.5496(2) 0.3711(4) 0.0480(9) Uani 1 1 d . . . C1 C -0.4736(5) 0.5507(4) 0.2411(5) 0.0775(15) Uani 1 1 d . . . H1A H -0.4643 0.5864 0.1682 0.116 Uiso 1 1 calc R . . H1B H -0.5538 0.5673 0.2724 0.116 Uiso 1 1 calc R . . H1C H -0.4943 0.4989 0.1998 0.116 Uiso 1 1 calc R . . O1 O -0.2179(3) 0.52445(18) 0.3479(3) 0.0529(7) Uani 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 0.0380(4) 0.0591(5) 0.0390(4) 0.0001(4) 0.0205(3) 0.0032(3) O2 0.0384(13) 0.0681(17) 0.0373(12) -0.0042(12) 0.0173(10) 0.0063(12) C4 0.0376(17) 0.0460(18) 0.0411(18) 0.0036(15) 0.0209(14) 0.0007(14) N1 0.0647(16) 0.0588(14) 0.0977(19) 0.0060(14) 0.0521(15) 0.0058(13) C5 0.0421(18) 0.049(2) 0.0486(19) 0.0000(16) 0.0273(16) -0.0029(15) C6 0.060(2) 0.054(2) 0.047(2) -0.0012(18) 0.0291(18) -0.0002(18) C8 0.098(4) 0.088(4) 0.069(3) -0.017(3) 0.057(3) -0.007(3) C10 0.070(3) 0.058(2) 0.070(3) 0.004(2) 0.040(2) 0.014(2) C7 0.084(3) 0.080(3) 0.049(2) -0.002(2) 0.038(2) -0.004(3) C9 0.090(4) 0.075(3) 0.102(4) -0.011(3) 0.064(3) 0.016(3) C15 0.0711(17) 0.0629(16) 0.106(2) 0.0078(16) 0.0498(16) 0.0101(14) C3 0.0367(18) 0.064(2) 0.0423(18) 0.0073(17) 0.0172(15) 0.0070(16) C13 0.0714(18) 0.0602(16) 0.108(2) 0.0098(16) 0.0421(17) 0.0053(15) C16 0.072(3) 0.065(3) 0.118(5) 0.015(3) 0.010(3) -0.008(3) C11 0.0734(17) 0.0638(16) 0.110(2) 0.0039(16) 0.0536(16) 0.0031(15) C14 0.0756(18) 0.0625(16) 0.110(2) 0.0080(17) 0.0448(17) 0.0114(15) C12 0.0741(18) 0.0658(16) 0.114(2) 0.0069(17) 0.0511(17) 0.0005(15) C2 0.0381(18) 0.065(2) 0.0402(18) 0.0090(17) 0.0128(15) -0.0048(17) C1 0.045(2) 0.134(5) 0.048(2) 0.006(3) 0.0090(19) -0.004(3) O1 0.0443(14) 0.0798(19) 0.0358(13) 0.0028(13) 0.0155(11) 0.0029(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.121(2) 3_566 ? Mn1 O2 2.121(2) . ? Mn1 O1 2.130(3) 3_566 ? Mn1 O1 2.130(3) . ? Mn1 N1 2.342(4) . ? Mn1 N1 2.342(4) 3_566 ? O2 C4 1.259(4) . ? C4 C3 1.387(5) . ? C4 C5 1.488(5) . ? N1 C15 1.301(6) . ? N1 C11 1.309(6) . ? C5 C6 1.387(5) . ? C5 C10 1.387(5) . ? C6 C7 1.369(5) . ? C6 H6 0.93 . ? C8 C9 1.374(8) . ? C8 C7 1.375(7) . ? C8 H8 0.93 . ? C10 C9 1.382(7) . ? C10 H10 0.93 . ? C7 H7 0.93 . ? C9 H9 0.93 . ? C15 C14 1.368(7) . ? C15 H15 0.93 . ? C3 C2 1.397(5) . ? C3 H3 0.93 . ? C13 C14 1.355(7) . ? C13 C12 1.367(7) . ? C13 C16 1.510(7) . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C11 C12 1.375(7) . ? C11 H11 0.93 . ? C14 H14 0.93 . ? C12 H12 0.93 . ? C2 O1 1.245(4) . ? C2 C1 1.504(5) . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? 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 180.00(10) 3_566 . ? O2 Mn1 O1 83.66(10) 3_566 3_566 ? O2 Mn1 O1 96.34(10) . 3_566 ? O2 Mn1 O1 96.34(10) 3_566 . ? O2 Mn1 O1 83.66(10) . . ? O1 Mn1 O1 180.00(10) 3_566 . ? O2 Mn1 N1 88.95(12) 3_566 . ? O2 Mn1 N1 91.05(12) . . ? O1 Mn1 N1 89.49(13) 3_566 . ? O1 Mn1 N1 90.51(13) . . ? O2 Mn1 N1 91.05(12) 3_566 3_566 ? O2 Mn1 N1 88.95(12) . 3_566 ? O1 Mn1 N1 90.51(13) 3_566 3_566 ? O1 Mn1 N1 89.49(13) . 3_566 ? N1 Mn1 N1 180 . 3_566 ? C4 O2 Mn1 130.0(2) . . ? O2 C4 C3 125.2(3) . . ? O2 C4 C5 115.8(3) . . ? C3 C4 C5 119.0(3) . . ? C15 N1 C11 115.1(4) . . ? C15 N1 Mn1 122.7(3) . . ? C11 N1 Mn1 122.1(3) . . ? C6 C5 C10 118.7(4) . . ? C6 C5 C4 118.1(3) . . ? C10 C5 C4 123.2(4) . . ? C7 C6 C5 121.0(4) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C9 C8 C7 119.7(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C9 C10 C5 119.9(4) . . ? C9 C10 H10 120 . . ? C5 C10 H10 120 . . ? C6 C7 C8 120.1(5) . . ? C6 C7 H7 120 . . ? C8 C7 H7 120 . . ? C8 C9 C10 120.5(5) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? N1 C15 C14 124.5(5) . . ? N1 C15 H15 117.7 . . ? C14 C15 H15 117.7 . . ? C4 C3 C2 125.5(3) . . ? C4 C3 H3 117.2 . . ? C2 C3 H3 117.2 . . ? C14 C13 C12 113.6(5) . . ? C14 C13 C16 122.7(5) . . ? C12 C13 C16 123.6(5) . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C11 C12 123.5(5) . . ? N1 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C13 C14 C15 121.5(5) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C13 C12 C11 121.7(5) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? O1 C2 C3 125.7(3) . . ? O1 C2 C1 116.3(4) . . ? C3 C2 C1 118.0(4) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 O1 Mn1 129.6(2) . . ? _database_code_depnum_ccdc_archive 'CCDC 938355' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_35-DMePy _audit_creation_date 2012-09-18T15:32:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Bis(benzoylacetonato)bis(3,5-dimethylpyridine)manganese(II) ; _chemical_formula_sum 'C34 H36 Mn N2 O4' _chemical_formula_moiety 'C34 H36 Mn N2 O4' _chemical_formula_weight 591.59 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.5786(8) _cell_length_b 13.5686(12) _cell_length_c 18.240(2) _cell_angle_alpha 90 _cell_angle_beta 104.845(8) _cell_angle_gamma 90 _cell_volume 3248.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3833 _cell_measurement_theta_min 3.7250 _cell_measurement_theta_max 39.1383 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.21 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.444 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_unetI/netI 0.0476 _diffrn_reflns_number 10147 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 27 _diffrn_reflns_theta_full 27 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 3523 _reflns_number_gt 2133 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_cell_refinement ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_data_reduction ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_structure_solution ; 'SIR-92 (Altomare, Cascanaro, Giacovazzo, Gualardi, 1993)' ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ; WinGX (Farrugia, 1999) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0559P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3523 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.095 _refine_ls_wR_factor_gt 0.0876 _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_restrained_S_all 0.874 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.202 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.045 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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_ _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 0.75 0.25 0.5 0.05115(15) Uani 1 2 d S . . O2 O 0.89726(8) 0.28625(10) 0.56802(6) 0.0539(3) Uani 1 1 d U . . O1 O 0.81237(10) 0.28574(11) 0.40682(6) 0.0637(4) Uani 1 1 d . . . C4 C 0.97148(12) 0.32480(13) 0.54867(9) 0.0452(4) Uani 1 1 d U . . N1 N 0.70054(12) 0.41206(13) 0.50217(8) 0.0602(4) Uani 1 1 d . . . C2 C 0.89630(15) 0.32458(15) 0.40867(9) 0.0558(5) Uani 1 1 d . . . C5 C 1.06391(12) 0.34581(14) 0.61232(9) 0.0481(4) Uani 1 1 d . . . C3 C 0.97339(14) 0.34586(16) 0.47404(9) 0.0580(5) Uani 1 1 d . . . H3 H 1.0314 0.377 0.4671 0.07 Uiso 1 1 calc R . . C6 C 1.07235(14) 0.29905(19) 0.68076(10) 0.0730(6) Uani 1 1 d . . . H6 H 1.0213 0.2562 0.6863 0.088 Uiso 1 1 calc R . . C1 C 0.91611(17) 0.3483(2) 0.33229(10) 0.0832(7) Uani 1 1 d . . . H1A H 0.9506 0.2938 0.3161 0.125 Uiso 1 1 calc R . . H1B H 0.9578 0.4062 0.3368 0.125 Uiso 1 1 calc R . . H1C H 0.8525 0.3597 0.2956 0.125 Uiso 1 1 calc R . . C10 C 1.14218(15) 0.40792(17) 0.60625(11) 0.0698(6) Uani 1 1 d . . . H10 H 1.1395 0.4395 0.5605 0.084 Uiso 1 1 calc R . . C12 C 0.58676(15) 0.54135(18) 0.44499(12) 0.0684(6) Uani 1 1 d . . . C11 C 0.62139(15) 0.44574(17) 0.44828(11) 0.0651(6) Uani 1 1 d . . . H11 H 0.5879 0.402 0.4109 0.078 Uiso 1 1 calc R . . C8 C 1.23108(15) 0.3771(2) 0.73468(12) 0.0845(8) Uani 1 1 d . . . H8 H 1.2869 0.3881 0.7756 0.101 Uiso 1 1 calc R . . C15 C 0.74728(14) 0.47555(17) 0.55544(11) 0.0633(6) Uani 1 1 d . . . H15 H 0.8026 0.453 0.5931 0.076 Uiso 1 1 calc R . . C9 C 1.22424(16) 0.4232(2) 0.66773(13) 0.0871(8) Uani 1 1 d . . . H9 H 1.2758 0.466 0.6631 0.104 Uiso 1 1 calc R . . C14 C 0.71855(16) 0.57282(18) 0.55805(11) 0.0708(6) Uani 1 1 d . . . C13 C 0.63620(17) 0.60410(18) 0.50095(13) 0.0748(6) Uani 1 1 d . . . H13 H 0.6142 0.669 0.5007 0.09 Uiso 1 1 calc R . . C7 C 1.15634(16) 0.3153(2) 0.74153(11) 0.0912(9) Uani 1 1 d . . . H7 H 1.161 0.2831 0.7873 0.109 Uiso 1 1 calc R . . C16 C 0.49792(18) 0.5731(2) 0.38066(13) 0.0979(8) Uani 1 1 d . . . H16A H 0.4506 0.6104 0.4007 0.147 Uiso 1 1 calc R . . H16C H 0.4644 0.5159 0.3548 0.147 Uiso 1 1 calc R . . H16B H 0.5224 0.6132 0.3457 0.147 Uiso 1 1 calc R . . C17 C 0.7740(2) 0.6401(2) 0.62012(15) 0.1139(10) Uani 1 1 d . . . H17C H 0.8324 0.6067 0.6508 0.171 Uiso 1 1 calc R . . H17A H 0.7294 0.6588 0.651 0.171 Uiso 1 1 calc R . . H17B H 0.7957 0.698 0.5983 0.171 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0416(2) 0.0623(3) 0.0425(2) -0.00158(19) -0.00209(15) 0.0044(2) O2 0.0429(6) 0.0757(9) 0.0381(6) 0.0011(6) 0.0009(5) -0.0010(6) O1 0.0596(8) 0.0866(11) 0.0379(7) -0.0022(6) 0.0000(6) -0.0003(7) C4 0.0458(8) 0.0458(11) 0.0414(9) -0.0022(8) 0.0062(7) 0.0088(8) N1 0.0559(9) 0.0646(11) 0.0551(9) -0.0001(8) 0.0054(7) 0.0107(9) C2 0.0620(12) 0.0619(13) 0.0401(10) 0.0033(9) 0.0069(9) 0.0115(10) C5 0.0434(9) 0.0574(12) 0.0405(9) -0.0044(8) 0.0052(7) 0.0036(9) C3 0.0557(10) 0.0736(15) 0.0411(10) 0.0031(9) 0.0061(8) -0.0034(10) C6 0.0540(11) 0.1147(19) 0.0445(11) 0.0086(11) 0.0019(9) -0.0162(12) C1 0.0918(16) 0.112(2) 0.0418(11) 0.0093(12) 0.0103(10) -0.0055(15) C10 0.0665(12) 0.0837(17) 0.0546(11) 0.0028(11) 0.0075(10) -0.0139(12) C12 0.0591(12) 0.0756(16) 0.0707(13) 0.0105(12) 0.0170(10) 0.0185(12) C11 0.0595(11) 0.0719(16) 0.0577(12) 0.0010(10) 0.0038(9) 0.0090(11) C8 0.0519(12) 0.132(2) 0.0597(14) -0.0164(14) -0.0028(10) -0.0140(14) C15 0.0572(11) 0.0734(16) 0.0562(12) -0.0015(11) 0.0092(9) 0.0134(11) C9 0.0610(13) 0.118(2) 0.0779(15) -0.0112(15) 0.0094(12) -0.0338(14) C14 0.0660(12) 0.0735(17) 0.0734(14) -0.0110(12) 0.0190(11) 0.0079(12) C13 0.0749(13) 0.0645(15) 0.0871(15) 0.0000(13) 0.0248(12) 0.0180(12) C7 0.0669(13) 0.149(3) 0.0476(12) 0.0110(13) -0.0033(10) -0.0206(16) C16 0.0822(15) 0.103(2) 0.0981(18) 0.0203(15) 0.0037(13) 0.0363(15) C17 0.107(2) 0.102(2) 0.121(2) -0.0479(18) 0.0082(17) 0.0063(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.1232(11) . ? Mn1 O2 2.1233(11) 7_656 ? Mn1 O1 2.1397(14) 7_656 ? Mn1 O1 2.1398(14) . ? Mn1 N1 2.3025(17) 7_656 ? Mn1 N1 2.3026(17) . ? O2 C4 1.263(2) . ? O1 C2 1.248(2) . ? C4 C3 1.398(2) . ? C4 C5 1.503(2) . ? N1 C15 1.331(2) . ? N1 C11 1.337(2) . ? C2 C3 1.400(2) . ? C2 C1 1.519(3) . ? C5 C6 1.379(2) . ? C5 C10 1.383(3) . ? C3 H3 0.93 . ? C6 C7 1.389(2) . ? C6 H6 0.93 . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C10 C9 1.379(3) . ? C10 H10 0.93 . ? C12 C13 1.366(3) . ? C12 C11 1.376(3) . ? C12 C16 1.514(3) . ? C11 H11 0.93 . ? C8 C7 1.347(3) . ? C8 C9 1.354(3) . ? C8 H8 0.93 . ? C15 C14 1.381(3) . ? C15 H15 0.93 . ? C9 H9 0.93 . ? C14 C13 1.385(3) . ? C14 C17 1.498(3) . ? C13 H13 0.93 . ? C7 H7 0.93 . ? C16 H16A 0.96 . ? C16 H16C 0.96 . ? C16 H16B 0.96 . ? C17 H17C 0.96 . ? C17 H17A 0.96 . ? C17 H17B 0.96 . ? 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 180 . 7_656 ? O2 Mn1 O1 95.37(5) . 7_656 ? O2 Mn1 O1 84.64(5) 7_656 7_656 ? O2 Mn1 O1 84.63(5) . . ? O2 Mn1 O1 95.36(5) 7_656 . ? O1 Mn1 O1 180 7_656 . ? O2 Mn1 N1 89.78(5) . 7_656 ? O2 Mn1 N1 90.22(5) 7_656 7_656 ? O1 Mn1 N1 88.49(6) 7_656 7_656 ? O1 Mn1 N1 91.50(6) . 7_656 ? O2 Mn1 N1 90.22(5) . . ? O2 Mn1 N1 89.78(5) 7_656 . ? O1 Mn1 N1 91.50(6) 7_656 . ? O1 Mn1 N1 88.50(6) . . ? N1 Mn1 N1 180.00(8) 7_656 . ? C4 O2 Mn1 129.20(10) . . ? C2 O1 Mn1 128.22(11) . . ? O2 C4 C3 124.88(15) . . ? O2 C4 C5 115.53(14) . . ? C3 C4 C5 119.56(16) . . ? C15 N1 C11 117.28(18) . . ? C15 N1 Mn1 122.94(12) . . ? C11 N1 Mn1 119.78(13) . . ? O1 C2 C3 126.03(17) . . ? O1 C2 C1 116.06(16) . . ? C3 C2 C1 117.89(19) . . ? C6 C5 C10 117.75(16) . . ? C6 C5 C4 118.13(17) . . ? C10 C5 C4 124.11(16) . . ? C4 C3 C2 126.21(18) . . ? C4 C3 H3 116.9 . . ? C2 C3 H3 116.9 . . ? C5 C6 C7 120.7(2) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C9 C10 C5 120.27(19) . . ? C9 C10 H10 119.9 . . ? C5 C10 H10 119.9 . . ? C13 C12 C11 117.26(18) . . ? C13 C12 C16 122.9(2) . . ? C11 C12 C16 119.9(2) . . ? N1 C11 C12 123.74(19) . . ? N1 C11 H11 118.1 . . ? C12 C11 H11 118.1 . . ? C7 C8 C9 119.49(18) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? N1 C15 C14 123.89(17) . . ? N1 C15 H15 118.1 . . ? C14 C15 H15 118.1 . . ? C8 C9 C10 121.2(2) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C15 C14 C13 116.60(19) . . ? C15 C14 C17 121.1(2) . . ? C13 C14 C17 122.3(2) . . ? C12 C13 C14 121.2(2) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C8 C7 C6 120.6(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? H16C C16 H16B 109.5 . . ? C14 C17 H17C 109.5 . . ? C14 C17 H17A 109.5 . . ? H17C C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17C C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? _database_code_depnum_ccdc_archive 'CCDC 938356' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3AmPy _audit_creation_date 2013-01-03T16:13:47-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Bis(benzoylacetonato)bis(3-aminopyridine)manganese(II) ; _chemical_formula_sum 'C30 H30 Mn N4 O4' _chemical_formula_moiety 'C30 H30 Mn N4 O4' _chemical_formula_weight 565.52 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 7.5573(3) _cell_length_b 17.7535(7) _cell_length_c 10.6145(4) _cell_angle_alpha 90 _cell_angle_beta 101.146(3) _cell_angle_gamma 90 _cell_volume 1397.27(9) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4954 _cell_measurement_theta_min 3.8080 _cell_measurement_theta_max 40.0943 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour orange _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 590 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.514 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_unetI/netI 0.0446 _diffrn_reflns_number 13272 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 26.99 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 3025 _reflns_number_gt 2011 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_cell_refinement ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_data_reduction ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_structure_solution ; 'SIR-92 (Altomare, Cascanaro, Giacovazzo, Gualardi, 1993)' ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ; WinGX (Farrugia, 1999) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0388P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3025 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0712 _refine_ls_wR_factor_gt 0.0668 _refine_ls_goodness_of_fit_ref 0.907 _refine_ls_restrained_S_all 0.907 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.209 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.033 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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_ _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 0.5 0 0.5 0.03768(12) Uani 1 2 d S . . O1 O 0.66917(14) 0.09512(7) 0.48555(11) 0.0433(3) Uani 1 1 d . . . O2 O 0.30501(14) 0.05857(7) 0.36753(11) 0.0438(3) Uani 1 1 d . . . N1 N 0.38130(18) 0.05197(8) 0.66807(14) 0.0430(4) Uani 1 1 d . . . C12 C 0.1239(2) 0.09927(9) 0.74504(16) 0.0391(4) Uani 1 1 d . . . C5 C 0.1617(2) 0.13939(9) 0.20515(15) 0.0361(4) Uani 1 1 d . . . C10 C 0.1307(2) 0.21362(10) 0.16593(16) 0.0436(4) Uani 1 1 d . . . H10 H 0.218 0.25 0.1939 0.052 Uiso 1 1 calc R . . C4 C 0.3273(2) 0.11506(9) 0.29845(15) 0.0359(4) Uani 1 1 d . . . C11 C 0.2082(2) 0.07234(10) 0.64902(16) 0.0435(4) Uani 1 1 d . . . H11 H 0.14 0.0682 0.5664 0.052 Uiso 1 1 calc R . . C3 C 0.4893(2) 0.15384(10) 0.30418(16) 0.0405(4) Uani 1 1 d . . . H3 H 0.4918 0.1905 0.2419 0.049 Uiso 1 1 calc R . . C2 C 0.6487(2) 0.14286(10) 0.39481(16) 0.0385(4) Uani 1 1 d . . . C13 C 0.2288(2) 0.10460(10) 0.86711(17) 0.0471(5) Uani 1 1 d . . . H13 H 0.1789 0.1225 0.9348 0.057 Uiso 1 1 calc R . . C9 C -0.0288(2) 0.23386(11) 0.08555(18) 0.0518(5) Uani 1 1 d . . . H9 H -0.0496 0.2839 0.0615 0.062 Uiso 1 1 calc R . . C6 C 0.0306(2) 0.08609(11) 0.16103(18) 0.0472(5) Uani 1 1 d . . . H6 H 0.0488 0.0362 0.1873 0.057 Uiso 1 1 calc R . . C8 C -0.1564(2) 0.18025(13) 0.04130(19) 0.0574(5) Uani 1 1 d . . . H8 H -0.2628 0.1939 -0.0137 0.069 Uiso 1 1 calc R . . C1 C 0.8084(2) 0.19237(12) 0.38937(19) 0.0539(5) Uani 1 1 d . . . H1A H 0.8392 0.2206 0.4677 0.081 Uiso 1 1 calc R . . H1C H 0.779 0.2265 0.3182 0.081 Uiso 1 1 calc R . . H1B H 0.9091 0.1617 0.3787 0.081 Uiso 1 1 calc R . . C14 C 0.4056(2) 0.08335(11) 0.88750(18) 0.0532(5) Uani 1 1 d . . . H14 H 0.4766 0.0864 0.9693 0.064 Uiso 1 1 calc R . . C15 C 0.4777(2) 0.05764(11) 0.78715(18) 0.0511(5) Uani 1 1 d . . . H15 H 0.5985 0.0435 0.8023 0.061 Uiso 1 1 calc R . . C7 C -0.1268(2) 0.10619(12) 0.0784(2) 0.0595(5) Uani 1 1 d . . . H7 H -0.2128 0.0697 0.0479 0.071 Uiso 1 1 calc R . . N2 N -0.0540(2) 0.12061(12) 0.72029(18) 0.0617(5) Uani 1 1 d . . . H16 H -0.102(3) 0.1310(14) 0.787(3) 0.093 Uiso 1 1 d . . . H17 H -0.118(3) 0.1111(14) 0.651(3) 0.093 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 0.03505(19) 0.0437(2) 0.0334(2) 0.00567(18) 0.00451(14) 0.00313(18) O1 0.0356(6) 0.0517(7) 0.0404(7) 0.0037(6) 0.0017(5) -0.0037(6) O2 0.0367(6) 0.0508(7) 0.0422(7) 0.0142(6) 0.0035(5) -0.0010(6) N1 0.0383(7) 0.0503(9) 0.0399(8) -0.0017(7) 0.0066(6) 0.0018(7) C12 0.0381(9) 0.0391(10) 0.0390(10) -0.0024(7) 0.0046(7) 0.0012(8) C5 0.0369(9) 0.0434(10) 0.0285(8) 0.0045(7) 0.0080(7) 0.0009(8) C10 0.0437(10) 0.0473(11) 0.0401(10) 0.0066(8) 0.0089(8) -0.0039(9) C4 0.0400(9) 0.0419(9) 0.0266(8) -0.0013(7) 0.0088(7) 0.0030(8) C11 0.0436(10) 0.0491(11) 0.0349(10) -0.0032(8) 0.0005(8) 0.0037(9) C3 0.0401(9) 0.0476(10) 0.0344(9) 0.0063(8) 0.0087(7) -0.0039(8) C2 0.0385(9) 0.0432(10) 0.0360(9) -0.0051(8) 0.0128(7) -0.0006(8) C13 0.0453(10) 0.0568(12) 0.0396(10) -0.0104(9) 0.0090(8) -0.0018(9) C9 0.0541(11) 0.0525(12) 0.0503(11) 0.0209(9) 0.0135(9) 0.0102(10) C6 0.0447(10) 0.0441(10) 0.0496(11) 0.0076(8) 0.0012(8) -0.0004(9) C8 0.0405(10) 0.0760(15) 0.0514(12) 0.0191(10) -0.0021(9) 0.0070(11) C1 0.0431(10) 0.0641(13) 0.0560(12) 0.0022(10) 0.0134(9) -0.0088(10) C14 0.0440(10) 0.0736(13) 0.0374(10) -0.0090(9) -0.0033(8) 0.0010(10) C15 0.0354(9) 0.0679(13) 0.0474(11) -0.0049(10) 0.0017(8) 0.0025(9) C7 0.0448(10) 0.0642(14) 0.0626(13) 0.0061(11) -0.0068(9) -0.0058(10) N2 0.0431(9) 0.0885(13) 0.0505(11) -0.0155(10) 0.0016(8) 0.0172(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.1044(10) . ? Mn1 O2 2.1044(10) 3_656 ? Mn1 O1 2.1413(11) 3_656 ? Mn1 O1 2.1414(11) . ? Mn1 N1 2.3361(14) 3_656 ? Mn1 N1 2.3361(14) . ? O1 C2 1.2699(19) . ? O2 C4 1.2727(19) . ? N1 C11 1.335(2) . ? N1 C15 1.335(2) . ? C12 N2 1.373(2) . ? C12 C13 1.385(2) . ? C12 C11 1.387(2) . ? C5 C6 1.384(2) . ? C5 C10 1.388(2) . ? C5 C4 1.501(2) . ? C10 C9 1.383(2) . ? C10 H10 0.93 . ? C4 C3 1.396(2) . ? C11 H11 0.93 . ? C3 C2 1.402(2) . ? C3 H3 0.93 . ? C2 C1 1.503(2) . ? C13 C14 1.365(2) . ? C13 H13 0.93 . ? C9 C8 1.372(3) . ? C9 H9 0.93 . ? C6 C7 1.381(2) . ? C6 H6 0.93 . ? C8 C7 1.379(3) . ? C8 H8 0.93 . ? C1 H1A 0.96 . ? C1 H1C 0.96 . ? C1 H1B 0.96 . ? C14 C15 1.365(3) . ? C14 H14 0.93 . ? C15 H15 0.93 . ? C7 H7 0.93 . ? N2 H16 0.87(3) . ? N2 H17 0.82(2) . ? 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 180 . 3_656 ? O2 Mn1 O1 94.98(4) . 3_656 ? O2 Mn1 O1 85.02(4) 3_656 3_656 ? O2 Mn1 O1 85.02(4) . . ? O2 Mn1 O1 94.98(4) 3_656 . ? O1 Mn1 O1 180.00(4) 3_656 . ? O2 Mn1 N1 90.43(5) . 3_656 ? O2 Mn1 N1 89.57(5) 3_656 3_656 ? O1 Mn1 N1 93.78(5) 3_656 3_656 ? O1 Mn1 N1 86.22(5) . 3_656 ? O2 Mn1 N1 89.57(5) . . ? O2 Mn1 N1 90.43(5) 3_656 . ? O1 Mn1 N1 86.22(5) 3_656 . ? O1 Mn1 N1 93.78(5) . . ? N1 Mn1 N1 180 3_656 . ? C2 O1 Mn1 126.44(10) . . ? C4 O2 Mn1 128.37(10) . . ? C11 N1 C15 117.55(15) . . ? C11 N1 Mn1 120.08(11) . . ? C15 N1 Mn1 122.21(11) . . ? N2 C12 C13 121.48(17) . . ? N2 C12 C11 121.76(16) . . ? C13 C12 C11 116.76(15) . . ? C6 C5 C10 118.64(15) . . ? C6 C5 C4 118.50(15) . . ? C10 C5 C4 122.79(15) . . ? C9 C10 C5 120.53(17) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? O2 C4 C3 125.19(15) . . ? O2 C4 C5 114.86(14) . . ? C3 C4 C5 119.95(15) . . ? N1 C11 C12 123.91(15) . . ? N1 C11 H11 118 . . ? C12 C11 H11 118 . . ? C4 C3 C2 126.25(16) . . ? C4 C3 H3 116.9 . . ? C2 C3 H3 116.9 . . ? O1 C2 C3 125.14(15) . . ? O1 C2 C1 116.01(15) . . ? C3 C2 C1 118.81(16) . . ? C14 C13 C12 119.66(16) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C8 C9 C10 120.15(17) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C7 C6 C5 120.69(17) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C9 C8 C7 119.96(16) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? H1C C1 H1B 109.5 . . ? C13 C14 C15 119.65(17) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? N1 C15 C14 122.47(16) . . ? N1 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C8 C7 C6 120.01(18) . . ? C8 C7 H7 120 . . ? C6 C7 H7 120 . . ? C12 N2 H16 116.7(16) . . ? C12 N2 H17 120.3(17) . . ? H16 N2 H17 120(2) . . ? _database_code_depnum_ccdc_archive 'CCDC 938357' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2Am3MePy _audit_creation_date 2012-09-18T17:05:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Bis(benzoylacetonato)bis(2-amino-3-methylpyridine)manganese(II) ; _chemical_formula_sum 'C32 H34 Mn N4 O4' _chemical_formula_moiety 'C32 H34 Mn N4 O4' _chemical_formula_weight 593.57 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3008(6) _cell_length_b 17.1487(10) _cell_length_c 13.0737(13) _cell_angle_alpha 90 _cell_angle_beta 113.591(7) _cell_angle_gamma 90 _cell_volume 1500.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2699 _cell_measurement_theta_min 3.6946 _cell_measurement_theta_max 38.6769 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 622 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.482 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_unetI/netI 0.0559 _diffrn_reflns_number 7284 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.978 _diffrn_measured_fraction_theta_max 0.978 _reflns_number_total 2577 _reflns_number_gt 1525 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_cell_refinement ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_data_reduction ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_structure_solution ; 'SIR-92 (Altomare, Cascanaro, Giacovazzo, Gualardi, 1993)' ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ; WinGX (Farrugia, 1999) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0442P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2577 _refine_ls_number_parameters 197 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_restrained_S_all 0.924 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.208 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.038 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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_ _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 H2 H 0.629(3) 0.0486(13) 0.1269(19) 0.023(7) Uiso 1 1 d . . . H1 H 0.423(4) 0.0479(16) 0.053(2) 0.048(9) Uiso 1 1 d . . . O2 O -0.1387(2) -0.09062(10) 0.04905(14) 0.0387(5) Uani 1 1 d . . . O1 O 0.1169(2) -0.09047(11) -0.07212(15) 0.0418(5) Uani 1 1 d . . . C11 C 0.4777(3) 0.00757(16) 0.1994(2) 0.0352(6) Uani 1 1 d . . . C3 C 0.0032(4) -0.19906(14) -0.0015(3) 0.0499(7) Uani 1 1 d . . . H3 H 0.0147 -0.253 0.0047 0.06 Uiso 1 1 calc R . . C12 C 0.6306(3) -0.00123(19) 0.3067(2) 0.0444(6) Uani 1 1 d U . . C2 C 0.1065(4) -0.16278(17) -0.0586(2) 0.0424(7) Uani 1 1 d . . . C1 C 0.2159(5) -0.21471(18) -0.1096(3) 0.0648(10) Uani 1 1 d . . . H1A H 0.1327 -0.2236 -0.1869 0.097 Uiso 1 1 calc R . . H1B H 0.2467 -0.2637 -0.0708 0.097 Uiso 1 1 calc R . . H1C H 0.3375 -0.1897 -0.1035 0.097 Uiso 1 1 calc R . . C4 C -0.1132(3) -0.16451(16) 0.0464(2) 0.0363(7) Uani 1 1 d . . . C5 C -0.2180(4) -0.21294(15) 0.1016(2) 0.0369(6) Uani 1 1 d U . . N1 N 0.2885(3) -0.01667(11) 0.17384(17) 0.0354(6) Uani 1 1 d . . . C13 C 0.5826(4) -0.03749(17) 0.3853(2) 0.0519(7) Uani 1 1 d U . . H13 H 0.6803 -0.0444 0.4569 0.062 Uiso 1 1 calc R . . C15 C 0.2528(4) -0.05200(15) 0.2562(2) 0.0446(7) Uani 1 1 d . . . H15 H 0.1234 -0.0692 0.2399 0.053 Uiso 1 1 calc R . . C10 C -0.2191(4) -0.29354(16) 0.1008(3) 0.0547(8) Uani 1 1 d U . . H10 H -0.155 -0.3202 0.0626 0.066 Uiso 1 1 calc R . . C14 C 0.3914(4) -0.06417(16) 0.3604(2) 0.0500(7) Uani 1 1 d . . . H14 H 0.359 -0.0897 0.4137 0.06 Uiso 1 1 calc R . . C8 C -0.4104(5) -0.29794(19) 0.2112(3) 0.0689(9) Uani 1 1 d U . . H8 H -0.4733 -0.3265 0.2483 0.083 Uiso 1 1 calc R . . C9 C -0.3139(5) -0.33479(17) 0.1556(3) 0.0710(10) Uani 1 1 d U . . H9 H -0.3117 -0.389 0.1544 0.085 Uiso 1 1 calc R . . C6 C -0.3185(5) -0.17667(16) 0.1570(3) 0.0653(9) Uani 1 1 d U . . H6 H -0.3227 -0.1225 0.1578 0.078 Uiso 1 1 calc R . . C16 C 0.8378(4) 0.0304(2) 0.3318(3) 0.0783(11) Uani 1 1 d . . . H16A H 0.9245 0.0179 0.4073 0.117 Uiso 1 1 calc R . . H16B H 0.8312 0.086 0.3224 0.117 Uiso 1 1 calc R . . H16C H 0.8891 0.0074 0.2817 0.117 Uiso 1 1 calc R . . C7 C -0.4142(5) -0.21868(19) 0.2120(3) 0.0788(10) Uani 1 1 d U . . H7 H -0.4809 -0.1926 0.2494 0.095 Uiso 1 1 calc R . . N2 N 0.5156(4) 0.04121(15) 0.1170(2) 0.0468(6) Uani 1 1 d . . . Mn1 Mn 0 0 0 0.03659(18) Uani 1 2 d S . . 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 O2 0.0416(10) 0.0242(11) 0.0577(13) 0.0039(9) 0.0276(10) -0.0001(8) O1 0.0442(11) 0.0356(12) 0.0540(12) 0.0019(9) 0.0284(10) -0.0013(8) C11 0.0398(15) 0.0300(14) 0.0397(15) -0.0029(14) 0.0199(12) 0.0034(12) C3 0.0629(16) 0.0279(13) 0.0736(19) 0.0031(18) 0.0428(15) -0.0002(17) C12 0.0407(14) 0.0519(15) 0.0412(15) -0.0022(17) 0.0172(12) 0.0031(16) C2 0.0419(17) 0.036(2) 0.051(2) -0.0012(14) 0.0198(16) 0.0013(13) C1 0.084(2) 0.046(2) 0.088(3) -0.0020(18) 0.060(2) 0.0038(17) C4 0.0350(16) 0.0299(18) 0.0429(18) 0.0020(13) 0.0145(14) -0.0008(12) C5 0.0405(15) 0.0288(12) 0.0433(17) 0.0051(12) 0.0187(12) -0.0013(12) N1 0.0369(12) 0.0335(15) 0.0410(13) -0.0023(9) 0.0210(10) -0.0017(8) C13 0.0566(19) 0.0559(18) 0.0376(17) 0.0010(14) 0.0129(15) 0.0064(14) C15 0.0515(17) 0.0374(16) 0.0528(19) -0.0042(14) 0.0293(16) -0.0071(13) C10 0.074(2) 0.0310(12) 0.077(2) 0.0034(15) 0.0491(17) 0.0024(14) C14 0.070(2) 0.0469(17) 0.0404(18) 0.0022(14) 0.0293(17) -0.0046(15) C8 0.098(2) 0.0470(14) 0.088(3) 0.0097(17) 0.065(2) -0.0116(17) C9 0.102(3) 0.0290(15) 0.108(3) 0.0116(16) 0.069(2) -0.0030(15) C6 0.101(2) 0.0283(14) 0.100(3) 0.0045(16) 0.075(2) 0.0002(15) C16 0.0450(19) 0.119(3) 0.059(2) 0.011(2) 0.0090(17) -0.0077(17) C7 0.116(3) 0.0518(15) 0.110(3) -0.0002(18) 0.090(2) -0.0052(17) N2 0.0321(16) 0.0663(17) 0.0439(17) 0.0063(14) 0.0170(14) -0.0041(12) Mn1 0.0406(3) 0.0259(3) 0.0497(4) 0.0029(3) 0.0249(3) -0.0025(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2 C4 1.283(3) . ? O2 Mn1 2.0909(16) . ? O1 C2 1.259(3) . ? O1 Mn1 2.1608(17) . ? C11 N2 1.346(3) . ? C11 N1 1.350(3) . ? C11 C12 1.408(3) . ? C3 C4 1.375(3) . ? C3 C2 1.401(3) . ? C3 H3 0.93 . ? C12 C13 1.361(4) . ? C12 C16 1.514(4) . ? C2 C1 1.518(3) . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C4 C5 1.497(3) . ? C5 C6 1.369(3) . ? C5 C10 1.382(4) . ? N1 C15 1.348(3) . ? N1 Mn1 2.419(2) . ? C13 C14 1.379(4) . ? C13 H13 0.93 . ? C15 C14 1.349(4) . ? C15 H15 0.93 . ? C10 C9 1.374(4) . ? C10 H10 0.93 . ? C14 H14 0.93 . ? C8 C9 1.355(4) . ? C8 C7 1.360(4) . ? C8 H8 0.93 . ? C9 H9 0.93 . ? C6 C7 1.388(4) . ? C6 H6 0.93 . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C7 H7 0.93 . ? N2 H2 0.79(2) . ? N2 H1 0.84(3) . ? Mn1 O2 2.0909(16) 3 ? Mn1 O1 2.1609(17) 3 ? Mn1 N1 2.419(2) 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 C4 O2 Mn1 129.19(15) . . ? C2 O1 Mn1 126.10(17) . . ? N2 C11 N1 116.9(2) . . ? N2 C11 C12 120.6(2) . . ? N1 C11 C12 122.6(2) . . ? C4 C3 C2 127.8(2) . . ? C4 C3 H3 116.1 . . ? C2 C3 H3 116.1 . . ? C13 C12 C11 117.4(2) . . ? C13 C12 C16 122.5(3) . . ? C11 C12 C16 120.2(2) . . ? O1 C2 C3 126.0(2) . . ? O1 C2 C1 116.4(2) . . ? C3 C2 C1 117.6(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C4 C3 124.1(2) . . ? O2 C4 C5 115.3(2) . . ? C3 C4 C5 120.6(3) . . ? C6 C5 C10 117.1(2) . . ? C6 C5 C4 119.3(2) . . ? C10 C5 C4 123.6(2) . . ? C15 N1 C11 116.5(2) . . ? C15 N1 Mn1 115.44(16) . . ? C11 N1 Mn1 128.04(16) . . ? C12 C13 C14 121.1(3) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? N1 C15 C14 124.7(2) . . ? N1 C15 H15 117.6 . . ? C14 C15 H15 117.6 . . ? C9 C10 C5 120.9(3) . . ? C9 C10 H10 119.6 . . ? C5 C10 H10 119.6 . . ? C15 C14 C13 117.8(3) . . ? C15 C14 H14 121.1 . . ? C13 C14 H14 121.1 . . ? C9 C8 C7 119.2(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 121.2(3) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C5 C6 C7 121.7(3) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C8 C7 C6 119.9(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C11 N2 H2 118.2(17) . . ? C11 N2 H1 120.6(18) . . ? H2 N2 H1 121(2) . . ? O2 Mn1 O2 180 3 . ? O2 Mn1 O1 94.32(6) 3 . ? O2 Mn1 O1 85.68(6) . . ? O2 Mn1 O1 85.67(6) 3 3 ? O2 Mn1 O1 94.32(6) . 3 ? O1 Mn1 O1 180 . 3 ? O2 Mn1 N1 91.69(6) 3 . ? O2 Mn1 N1 88.31(6) . . ? O1 Mn1 N1 88.72(7) . . ? O1 Mn1 N1 91.28(7) 3 . ? O2 Mn1 N1 88.31(6) 3 3 ? O2 Mn1 N1 91.69(6) . 3 ? O1 Mn1 N1 91.28(7) . 3 ? O1 Mn1 N1 88.72(7) 3 3 ? N1 Mn1 N1 180 . 3 ? _database_code_depnum_ccdc_archive 'CCDC 938358' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_trans-2Am5MePy _audit_creation_date 2013-01-03T17:07:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Bis(benzoylacetonato)bis(2-amino-5-methylpyridine)manganese(II) ; _chemical_formula_sum 'C32 H34 Mn N4 O4' _chemical_formula_moiety 'C32 H34 Mn N4 O4' _chemical_formula_weight 593.57 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3129(16) _cell_length_b 8.752(2) _cell_length_c 24.543(7) _cell_angle_alpha 90 _cell_angle_beta 90.83(2) _cell_angle_gamma 90 _cell_volume 1570.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3548 _cell_measurement_theta_min 3.7397 _cell_measurement_theta_max 26.9999 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 622 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.461 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_unetI/netI 0.0587 _diffrn_reflns_number 12765 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 27.13 _diffrn_reflns_theta_full 27.13 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 3437 _reflns_number_gt 1791 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_cell_refinement ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_data_reduction ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_structure_solution ; 'SIR-92 (Altomare, Cascanaro, Giacovazzo, Gualardi, 1993)' ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ; WinGX (Farrugia, 1999) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0512P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3437 _refine_ls_number_parameters 197 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0945 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 0.832 _refine_ls_restrained_S_all 0.847 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.215 _refine_diff_density_min -0.14 _refine_diff_density_rms 0.031 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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_ _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 0.5 0.5 0.5 0.06466(19) Uani 1 2 d SU . . O2 O 0.33253(15) 0.38792(18) 0.55637(6) 0.0709(4) Uani 1 1 d . . . N1 N 0.3482(2) 0.3784(2) 0.42571(7) 0.0690(5) Uani 1 1 d U . . C12 C 0.3964(3) 0.2945(3) 0.33328(11) 0.0863(7) Uani 1 1 d U . . C11 C 0.4525(3) 0.3543(3) 0.38165(11) 0.0789(7) Uani 1 1 d U . . H11 H 0.5752 0.3814 0.3848 0.095 Uiso 1 1 calc R . . C5 C 0.2216(2) 0.2228(2) 0.62323(8) 0.0598(5) Uani 1 1 d DU . . C15 C 0.1705(3) 0.3366(3) 0.42082(11) 0.0673(6) Uani 1 1 d U . . C9 C 0.1054(4) 0.0664(4) 0.69521(11) 0.1060(9) Uani 1 1 d DU . . H9 H 0.1194 -0.017 0.7184 0.127 Uiso 1 1 calc R . . C4 C 0.3612(2) 0.2634(2) 0.58189(9) 0.0573(5) Uani 1 1 d . . . C3 C 0.5089(3) 0.1677(3) 0.57260(10) 0.0746(7) Uani 1 1 d . . . H3 H 0.5142 0.0789 0.5934 0.09 Uiso 1 1 calc R . . C6 C 0.0664(3) 0.3127(3) 0.62748(10) 0.0856(7) Uani 1 1 d DU . . H6 H 0.0528 0.3974 0.6049 0.103 Uiso 1 1 calc R . . C10 C 0.2384(3) 0.0988(3) 0.65770(9) 0.0842(7) Uani 1 1 d DU . . H10 H 0.3409 0.0363 0.6556 0.101 Uiso 1 1 calc R . . C7 C -0.0679(3) 0.2793(3) 0.66427(11) 0.1030(9) Uani 1 1 d DU . . H7 H -0.1722 0.3398 0.666 0.124 Uiso 1 1 calc R . . C8 C -0.0470(4) 0.1562(3) 0.69852(11) 0.1021(9) Uani 1 1 d DU . . H8 H -0.1363 0.134 0.7239 0.123 Uiso 1 1 calc R . . C13 C 0.2138(4) 0.2530(3) 0.32976(11) 0.0959(8) Uani 1 1 d U . . H13 H 0.1678 0.2106 0.2976 0.115 Uiso 1 1 calc R . . C14 C 0.1008(3) 0.2736(3) 0.37282(12) 0.0896(8) Uani 1 1 d U . . H14 H -0.0217 0.2457 0.3701 0.108 Uiso 1 1 calc R . . N2 N 0.0657(3) 0.3605(3) 0.46444(12) 0.0815(7) Uani 1 1 d . . . C16 C 0.5266(4) 0.2763(4) 0.28613(12) 0.1247(11) Uani 1 1 d . . . H16C H 0.5072 0.3577 0.2605 0.187 Uiso 1 1 calc R . . H16B H 0.5046 0.18 0.2685 0.187 Uiso 1 1 calc R . . H16A H 0.6505 0.2796 0.2996 0.187 Uiso 1 1 calc R . . C2 C 0.6508(2) 0.1890(3) 0.53567(10) 0.0654(6) Uani 1 1 d . . . C1 C 0.7901(3) 0.0616(3) 0.53095(12) 0.0992(9) Uani 1 1 d . . . H1C H 0.7722 0.0095 0.4969 0.149 Uiso 1 1 calc R . . H1B H 0.7751 -0.0092 0.5604 0.149 Uiso 1 1 calc R . . H1A H 0.9111 0.104 0.5326 0.149 Uiso 1 1 calc R . . O1 O 0.67303(15) 0.30304(18) 0.50588(6) 0.0675(4) Uani 1 1 d . . . H17 H -0.041(3) 0.330(3) 0.4638(9) 0.082(8) Uiso 1 1 d . . . H18 H 0.109(3) 0.383(3) 0.4958(9) 0.075(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 0.0406(2) 0.0657(3) 0.0882(4) 0.0185(3) 0.0165(2) 0.0149(2) O2 0.0460(7) 0.0729(11) 0.0943(11) 0.0252(9) 0.0197(7) 0.0151(7) N1 0.0482(9) 0.0735(14) 0.0857(13) 0.0085(10) 0.0131(8) 0.0134(9) C12 0.0854(15) 0.094(2) 0.0794(17) 0.0087(15) 0.0109(14) 0.0189(14) C11 0.0586(12) 0.0878(19) 0.0908(18) 0.0126(15) 0.0156(12) 0.0155(12) C5 0.0545(9) 0.0623(13) 0.0629(13) -0.0021(9) 0.0063(9) -0.0037(9) C15 0.0507(11) 0.0621(15) 0.0894(17) 0.0055(13) 0.0091(12) 0.0140(10) C9 0.1148(19) 0.109(2) 0.0953(19) 0.0270(16) 0.0351(15) -0.0048(14) C4 0.0456(10) 0.0582(14) 0.0681(14) 0.0068(12) 0.0023(9) 0.0018(10) C3 0.0656(12) 0.0589(15) 0.0999(18) 0.0255(13) 0.0205(12) 0.0166(11) C6 0.0734(13) 0.0900(18) 0.0943(18) 0.0152(13) 0.0317(12) 0.0164(11) C10 0.0813(14) 0.0846(17) 0.0873(18) 0.0190(13) 0.0178(11) 0.0048(12) C7 0.0822(15) 0.114(2) 0.115(2) 0.0030(15) 0.0457(14) 0.0095(14) C8 0.1011(16) 0.114(2) 0.092(2) -0.0004(14) 0.0467(15) -0.0174(14) C13 0.1027(18) 0.095(2) 0.0900(19) -0.0071(16) -0.0023(15) 0.0057(16) C14 0.0698(14) 0.094(2) 0.105(2) 0.0009(17) -0.0040(14) 0.0007(14) N2 0.0437(11) 0.0984(18) 0.103(2) -0.0052(14) 0.0107(13) 0.0035(10) C16 0.123(2) 0.155(3) 0.098(2) 0.006(2) 0.0352(18) 0.033(2) C2 0.0471(10) 0.0594(15) 0.0898(17) 0.0035(13) 0.0077(11) 0.0131(10) C1 0.0781(15) 0.0739(17) 0.147(2) 0.0167(17) 0.0335(15) 0.0329(13) O1 0.0421(7) 0.0672(10) 0.0937(12) 0.0156(9) 0.0157(7) 0.0169(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.1037(14) . ? Mn1 O2 2.1037(14) 3_666 ? Mn1 O1 2.1420(14) . ? Mn1 O1 2.1420(14) 3_666 ? Mn1 N1 2.3727(19) 3_666 ? Mn1 N1 2.3727(19) . ? O2 C4 1.273(2) . ? N1 C11 1.349(3) . ? N1 C15 1.354(2) . ? C12 C11 1.355(3) . ? C12 C13 1.386(3) . ? C12 C16 1.518(3) . ? C11 H11 0.93 . ? C5 C10 1.380(2) . ? C5 C6 1.386(2) . ? C5 C4 1.493(3) . ? C15 N2 1.342(3) . ? C15 C14 1.391(3) . ? C9 C8 1.368(3) . ? C9 C10 1.379(2) . ? C9 H9 0.93 . ? C4 C3 1.389(3) . ? C3 C2 1.400(3) . ? C3 H3 0.93 . ? C6 C7 1.375(2) . ? C6 H6 0.93 . ? C10 H10 0.93 . ? C7 C8 1.373(3) . ? C7 H7 0.93 . ? C8 H8 0.93 . ? C13 C14 1.363(3) . ? C13 H13 0.93 . ? C14 H14 0.93 . ? N2 H17 0.82(2) . ? N2 H18 0.85(2) . ? C16 H16C 0.96 . ? C16 H16B 0.96 . ? C16 H16A 0.96 . ? C2 O1 1.249(2) . ? C2 C1 1.515(3) . ? C1 H1C 0.96 . ? C1 H1B 0.96 . ? C1 H1A 0.96 . ? 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 180 . 3_666 ? O2 Mn1 O1 85.95(5) . . ? O2 Mn1 O1 94.05(5) 3_666 . ? O2 Mn1 O1 94.05(5) . 3_666 ? O2 Mn1 O1 85.95(5) 3_666 3_666 ? O1 Mn1 O1 180 . 3_666 ? O2 Mn1 N1 88.51(6) . 3_666 ? O2 Mn1 N1 91.49(6) 3_666 3_666 ? O1 Mn1 N1 92.28(6) . 3_666 ? O1 Mn1 N1 87.72(6) 3_666 3_666 ? O2 Mn1 N1 91.49(6) . . ? O2 Mn1 N1 88.51(6) 3_666 . ? O1 Mn1 N1 87.72(6) . . ? O1 Mn1 N1 92.28(6) 3_666 . ? N1 Mn1 N1 180 3_666 . ? C4 O2 Mn1 129.03(12) . . ? C11 N1 C15 116.1(2) . . ? C11 N1 Mn1 114.99(14) . . ? C15 N1 Mn1 128.84(15) . . ? C11 C12 C13 115.8(2) . . ? C11 C12 C16 121.5(2) . . ? C13 C12 C16 122.6(3) . . ? N1 C11 C12 126.5(2) . . ? N1 C11 H11 116.7 . . ? C12 C11 H11 116.7 . . ? C10 C5 C6 117.8(2) . . ? C10 C5 C4 123.24(18) . . ? C6 C5 C4 118.98(18) . . ? N2 C15 N1 116.5(2) . . ? N2 C15 C14 122.1(2) . . ? N1 C15 C14 121.4(2) . . ? C8 C9 C10 120.3(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? O2 C4 C3 123.97(19) . . ? O2 C4 C5 115.42(17) . . ? C3 C4 C5 120.60(19) . . ? C4 C3 C2 127.7(2) . . ? C4 C3 H3 116.1 . . ? C2 C3 H3 116.1 . . ? C7 C6 C5 121.5(2) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C9 C10 C5 120.9(2) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? C8 C7 C6 119.6(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C9 C8 C7 119.9(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 119.4(2) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C15 N2 H17 119.1(16) . . ? C15 N2 H18 123.4(14) . . ? H17 N2 H18 115(2) . . ? C12 C16 H16C 109.5 . . ? C12 C16 H16B 109.5 . . ? H16C C16 H16B 109.5 . . ? C12 C16 H16A 109.5 . . ? H16C C16 H16A 109.5 . . ? H16B C16 H16A 109.5 . . ? O1 C2 C3 126.11(18) . . ? O1 C2 C1 116.71(19) . . ? C3 C2 C1 117.2(2) . . ? C2 C1 H1C 109.5 . . ? C2 C1 H1B 109.5 . . ? H1C C1 H1B 109.5 . . ? C2 C1 H1A 109.5 . . ? H1C C1 H1A 109.5 . . ? H1B C1 H1A 109.5 . . ? C2 O1 Mn1 126.91(12) . . ? _database_code_depnum_ccdc_archive 'CCDC 938359' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cis-2Am5MePy _audit_creation_date 2013-01-03T16:25:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; cis-bis(Benzoylacetonato)bis(2-amino-5-methylpyridine)manganese(II) ; _chemical_formula_sum 'C32 H34 Mn N4 O4' _chemical_formula_moiety 'C32 H34 Mn N4 O4' _chemical_formula_weight 593.57 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1610(4) _cell_length_b 12.6475(5) _cell_length_c 12.9842(6) _cell_angle_alpha 85.849(4) _cell_angle_beta 73.618(4) _cell_angle_gamma 74.865(4) _cell_volume 1545.34(11) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5534 _cell_measurement_theta_min 4.005 _cell_measurement_theta_max 39.0601 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 622 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.468 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_av_unetI/netI 0.0491 _diffrn_reflns_number 11979 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.01 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _reflns_number_total 5965 _reflns_number_gt 4081 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_cell_refinement ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_data_reduction ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_structure_solution ; 'SIR-92 (Altomare, Cascanaro, Giacovazzo, Gualardi, 1993)' ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ; WinGX (Farrugia, 1999) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0965P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5965 _refine_ls_number_parameters 388 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.096 _refine_diff_density_min -0.793 _refine_diff_density_rms 0.061 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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_ _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 0.77055(5) 0.76470(4) 0.51015(4) 0.03783(18) Uani 1 1 d . . . O4 O 0.6052(2) 0.84779(17) 0.64561(16) 0.0440(5) Uani 1 1 d . . . O3 O 0.8875(2) 0.72225(18) 0.62993(17) 0.0463(5) Uani 1 1 d . . . O2 O 0.9643(2) 0.70196(18) 0.38885(17) 0.0472(6) Uani 1 1 d . . . O1 O 0.8286(2) 0.91887(18) 0.46607(19) 0.0503(6) Uani 1 1 d . . . N3 N 0.7014(3) 0.6021(2) 0.5411(2) 0.0414(6) Uani 1 1 d . . . N1 N 0.6365(3) 0.7944(2) 0.3846(2) 0.0427(6) Uani 1 1 d . . . C12 C 0.8502(3) 0.7442(3) 0.7281(3) 0.0464(8) Uani 1 1 d . . . N2 N 0.4303(4) 0.8976(3) 0.4944(3) 0.0607(9) Uani 1 1 d . . . C31 C 0.5725(3) 0.6122(3) 0.6131(3) 0.0483(8) Uani 1 1 d . . . H31 H 0.5243 0.6816 0.6412 0.058 Uiso 1 1 calc R . . C14 C 0.6000(3) 0.8489(2) 0.7449(2) 0.0387(7) Uani 1 1 d . . . C4 C 1.0389(3) 0.7524(3) 0.3159(2) 0.0438(8) Uani 1 1 d . . . C2 C 0.9302(3) 0.9400(3) 0.3921(3) 0.0478(8) Uani 1 1 d . . . C25 C 0.7052(4) 0.7462(3) 0.2886(3) 0.0516(8) Uani 1 1 d . . . H25 H 0.7982 0.7053 0.2796 0.062 Uiso 1 1 calc R . . C27 C 0.7698(3) 0.5021(3) 0.4998(3) 0.0443(8) Uani 1 1 d . . . C15 C 0.4602(4) 0.9028(4) 0.8200(3) 0.0600(6) Uani 1 1 d U . . C21 C 0.5018(4) 0.8522(3) 0.3983(3) 0.0470(8) Uani 1 1 d . . . C30 C 0.5077(4) 0.5298(3) 0.6478(3) 0.0547(9) Uani 1 1 d . . . C28 C 0.7099(4) 0.4130(3) 0.5319(3) 0.0596(10) Uani 1 1 d . . . H28 H 0.7585 0.3439 0.5032 0.072 Uiso 1 1 calc R . . C13 C 0.7151(3) 0.8036(3) 0.7852(3) 0.0528(9) Uani 1 1 d . . . H13 H 0.7012 0.8137 0.8581 0.063 Uiso 1 1 calc R . . C11 C 0.9600(4) 0.7013(4) 0.7889(3) 0.0711(12) Uani 1 1 d . . . H11A H 0.962 0.6264 0.8088 0.107 Uiso 1 1 calc R . . H11B H 0.9363 0.7446 0.8524 0.107 Uiso 1 1 calc R . . H11C H 1.0515 0.7056 0.7442 0.107 Uiso 1 1 calc R . . C20 C 0.4401(4) 0.9153(4) 0.9290(3) 0.0653(7) Uani 1 1 d U . . H20 H 0.5162 0.8882 0.9581 0.078 Uiso 1 1 calc R . . C22 C 0.4359(4) 0.8619(3) 0.3154(3) 0.0627(10) Uani 1 1 d . . . H22 H 0.3422 0.9017 0.3263 0.075 Uiso 1 1 calc R . . C6 C 1.1899(4) 0.5743(4) 0.2309(3) 0.0728(7) Uani 1 1 d U . . H6 H 1.1661 0.5408 0.2973 0.087 Uiso 1 1 calc R . . C5 C 1.1355(4) 0.6866(4) 0.2210(3) 0.0709(7) Uani 1 1 d U . . C3 C 1.0303(4) 0.8635(3) 0.3194(3) 0.0542(9) Uani 1 1 d . . . H3 H 1.0987 0.8896 0.2679 0.065 Uiso 1 1 calc R . . C24 C 0.6491(5) 0.7522(3) 0.2023(3) 0.0653(11) Uani 1 1 d . . . C16 C 0.3448(4) 0.9480(4) 0.7823(3) 0.0674(7) Uani 1 1 d U . . H16 H 0.3538 0.9426 0.7094 0.081 Uiso 1 1 calc R . . C1 C 0.9381(5) 1.0580(3) 0.3805(4) 0.0705(11) Uani 1 1 d . . . H1A H 0.8713 1.0982 0.3433 0.106 Uiso 1 1 calc R . . H1B H 1.0321 1.0614 0.3405 0.106 Uiso 1 1 calc R . . H1C H 0.9159 1.0894 0.4503 0.106 Uiso 1 1 calc R . . C18 C 0.1987(4) 1.0080(4) 0.9571(3) 0.0712(7) Uani 1 1 d U . . H18 H 0.1108 1.0407 1.0028 0.085 Uiso 1 1 calc R . . C29 C 0.5820(4) 0.4270(3) 0.6043(3) 0.0619(10) Uani 1 1 d . . . H29 H 0.5431 0.3673 0.6253 0.074 Uiso 1 1 calc R . . C23 C 0.5090(5) 0.8132(4) 0.2197(3) 0.0724(12) Uani 1 1 d . . . H23 H 0.4652 0.8205 0.1647 0.087 Uiso 1 1 calc R . . C7 C 1.2785(5) 0.5124(4) 0.1434(3) 0.0801(7) Uani 1 1 d U . . H7 H 1.316 0.4379 0.1514 0.096 Uiso 1 1 calc R . . C19 C 0.3097(4) 0.9671(4) 0.9957(3) 0.0696(7) Uani 1 1 d U . . H19 H 0.2996 0.9734 1.0686 0.084 Uiso 1 1 calc R . . C32 C 0.3651(5) 0.5493(4) 0.7282(3) 0.0815(13) Uani 1 1 d . . . H32A H 0.3753 0.5162 0.7954 0.122 Uiso 1 1 calc R . . H32B H 0.3042 0.5176 0.7025 0.122 Uiso 1 1 calc R . . H32C H 0.3245 0.6267 0.7383 0.122 Uiso 1 1 calc R . . C17 C 0.2156(4) 1.0012(4) 0.8488(3) 0.0725(7) Uani 1 1 d U . . H17 H 0.14 1.0325 0.8203 0.087 Uiso 1 1 calc R . . C8 C 1.3121(5) 0.5613(4) 0.0432(3) 0.0864(7) Uani 1 1 d U . . H8 H 1.372 0.5197 -0.0159 0.104 Uiso 1 1 calc R . . C26 C 0.7372(6) 0.6982(5) 0.0971(3) 0.0979(17) Uani 1 1 d . . . H26A H 0.7853 0.7483 0.053 0.147 Uiso 1 1 calc R . . H26B H 0.677 0.6776 0.0612 0.147 Uiso 1 1 calc R . . H26C H 0.8057 0.634 0.11 0.147 Uiso 1 1 calc R . . C10 C 1.1687(5) 0.7343(4) 0.1210(3) 0.0823(7) Uani 1 1 d U . . H10 H 1.1325 0.809 0.1128 0.099 Uiso 1 1 calc R . . C9 C 1.2566(5) 0.6705(4) 0.0323(4) 0.0880(7) Uani 1 1 d U . . H9 H 1.2775 0.703 -0.035 0.106 Uiso 1 1 calc R . . N4 N 0.8951(3) 0.4915(3) 0.4243(3) 0.0603(9) Uani 1 1 d . . . H34 H 0.464(4) 0.900(3) 0.541(3) 0.062(14) Uiso 1 1 d . . . H33 H 0.366(4) 0.950(3) 0.501(3) 0.063(13) Uiso 1 1 d . . . H35 H 0.939(5) 0.543(4) 0.411(4) 0.094 Uiso 1 1 d . . . H36 H 0.944(5) 0.432(4) 0.415(4) 0.094 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 0.0389(3) 0.0333(3) 0.0350(3) -0.00283(18) -0.00575(19) -0.00224(19) O4 0.0440(11) 0.0417(12) 0.0377(12) -0.0061(9) -0.0083(10) 0.0027(10) O3 0.0430(12) 0.0457(13) 0.0428(12) -0.0068(10) -0.0108(10) 0.0022(10) O2 0.0446(12) 0.0402(12) 0.0443(12) 0.0014(10) 0.0001(10) -0.0027(10) O1 0.0493(13) 0.0366(12) 0.0602(15) -0.0024(10) -0.0108(12) -0.0062(10) N3 0.0433(14) 0.0352(14) 0.0433(14) 0.0006(11) -0.0114(12) -0.0062(11) N1 0.0498(15) 0.0386(14) 0.0413(14) 0.0023(11) -0.0167(12) -0.0097(12) C12 0.0473(18) 0.0464(19) 0.0422(18) -0.0014(15) -0.0130(15) -0.0045(15) N2 0.056(2) 0.057(2) 0.062(2) -0.0103(17) -0.0231(18) 0.0096(17) C31 0.0510(19) 0.0451(19) 0.0469(19) -0.0016(15) -0.0114(16) -0.0107(16) C14 0.0458(16) 0.0304(15) 0.0362(16) -0.0036(12) -0.0065(14) -0.0075(13) C4 0.0349(15) 0.053(2) 0.0397(17) 0.0051(15) -0.0089(14) -0.0078(14) C2 0.0462(18) 0.0453(19) 0.056(2) 0.0055(16) -0.0208(17) -0.0135(15) C25 0.062(2) 0.054(2) 0.0401(18) 0.0030(15) -0.0137(17) -0.0171(17) C27 0.0506(18) 0.0359(17) 0.0472(18) -0.0003(14) -0.0195(16) -0.0056(14) C15 0.0460(10) 0.0835(15) 0.0421(11) -0.0076(11) -0.0090(9) -0.0030(10) C21 0.058(2) 0.0345(17) 0.052(2) 0.0069(15) -0.0232(17) -0.0100(15) C30 0.058(2) 0.066(2) 0.047(2) 0.0036(17) -0.0163(17) -0.0268(19) C28 0.078(3) 0.0367(19) 0.070(2) -0.0020(17) -0.030(2) -0.0131(18) C13 0.0495(18) 0.066(2) 0.0347(17) -0.0074(15) -0.0123(15) 0.0033(17) C11 0.058(2) 0.090(3) 0.057(2) -0.006(2) -0.0233(19) 0.005(2) C20 0.0504(11) 0.0880(15) 0.0449(11) -0.0074(11) -0.0066(9) -0.0009(11) C22 0.071(2) 0.057(2) 0.071(3) 0.012(2) -0.041(2) -0.014(2) C6 0.0782(13) 0.0791(15) 0.0479(11) -0.0086(11) 0.0009(11) -0.0145(12) C5 0.0770(14) 0.0782(15) 0.0463(11) -0.0069(11) 0.0008(11) -0.0173(12) C3 0.0477(18) 0.054(2) 0.057(2) 0.0059(17) -0.0067(17) -0.0164(17) C24 0.098(3) 0.061(2) 0.042(2) 0.0039(17) -0.023(2) -0.025(2) C16 0.0505(10) 0.0914(15) 0.0470(11) -0.0080(11) -0.0077(10) 0.0008(11) C1 0.075(3) 0.053(2) 0.092(3) 0.006(2) -0.029(2) -0.026(2) C18 0.0531(11) 0.0929(15) 0.0502(11) -0.0084(11) -0.0018(10) 0.0006(11) C29 0.077(3) 0.057(2) 0.063(2) 0.0123(19) -0.025(2) -0.033(2) C23 0.102(3) 0.073(3) 0.061(3) 0.012(2) -0.050(3) -0.025(3) C7 0.0855(14) 0.0833(15) 0.0530(12) -0.0101(12) 0.0043(11) -0.0120(12) C19 0.0538(11) 0.0914(15) 0.0476(11) -0.0080(11) -0.0029(10) -0.0004(11) C32 0.080(3) 0.103(4) 0.066(3) -0.002(2) -0.003(2) -0.048(3) C17 0.0535(11) 0.0954(15) 0.0513(11) -0.0080(11) -0.0048(10) 0.0028(11) C8 0.0928(14) 0.0880(15) 0.0555(12) -0.0094(12) 0.0078(11) -0.0112(13) C26 0.142(5) 0.112(4) 0.043(2) -0.008(2) -0.025(3) -0.036(4) C10 0.0908(14) 0.0844(15) 0.0521(12) -0.0050(12) 0.0056(11) -0.0144(13) C9 0.0960(14) 0.0891(15) 0.0553(12) -0.0059(12) 0.0083(11) -0.0127(13) N4 0.0513(18) 0.0403(17) 0.078(2) -0.0115(17) -0.0064(17) -0.0008(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.145(2) . ? Mn1 O4 2.168(2) . ? Mn1 O3 2.170(2) . ? Mn1 O1 2.174(2) . ? Mn1 N3 2.315(3) . ? Mn1 N1 2.356(3) . ? O4 C14 1.276(3) . ? O3 C12 1.252(4) . ? O2 C4 1.280(4) . ? O1 C2 1.268(4) . ? N3 C27 1.341(4) . ? N3 C31 1.359(4) . ? N1 C21 1.341(4) . ? N1 C25 1.345(4) . ? C12 C13 1.403(4) . ? C12 C11 1.511(5) . ? N2 C21 1.338(5) . ? N2 H34 0.78(4) . ? N2 H33 0.79(4) . ? C31 C30 1.357(5) . ? C31 H31 0.93 . ? C14 C13 1.386(5) . ? C14 C15 1.497(4) . ? C4 C3 1.389(5) . ? C4 C5 1.488(5) . ? C2 C3 1.391(5) . ? C2 C1 1.510(5) . ? C25 C24 1.383(5) . ? C25 H25 0.93 . ? C27 N4 1.351(5) . ? C27 C28 1.401(5) . ? C15 C16 1.369(5) . ? C15 C20 1.387(5) . ? C21 C22 1.402(5) . ? C30 C29 1.391(6) . ? C30 C32 1.499(5) . ? C28 C29 1.349(5) . ? C28 H28 0.93 . ? C13 H13 0.93 . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? C20 C19 1.384(5) . ? C20 H20 0.93 . ? C22 C23 1.352(6) . ? C22 H22 0.93 . ? C6 C7 1.378(5) . ? C6 C5 1.393(6) . ? C6 H6 0.93 . ? C5 C10 1.382(6) . ? C3 H3 0.93 . ? C24 C23 1.394(6) . ? C24 C26 1.503(6) . ? C16 C17 1.381(5) . ? C16 H16 0.93 . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C18 C19 1.329(5) . ? C18 C17 1.373(5) . ? C18 H18 0.93 . ? C29 H29 0.93 . ? C23 H23 0.93 . ? C7 C8 1.390(6) . ? C7 H7 0.93 . ? C19 H19 0.93 . ? C32 H32A 0.96 . ? C32 H32B 0.96 . ? C32 H32C 0.96 . ? C17 H17 0.93 . ? C8 C9 1.363(6) . ? C8 H8 0.93 . ? C26 H26A 0.96 . ? C26 H26B 0.96 . ? C26 H26C 0.96 . ? C10 C9 1.398(6) . ? C10 H10 0.93 . ? C9 H9 0.93 . ? N4 H35 0.86(5) . ? N4 H36 0.78(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 O2 Mn1 O4 166.47(9) . . ? O2 Mn1 O3 88.75(8) . . ? O4 Mn1 O3 82.20(8) . . ? O2 Mn1 O1 82.29(9) . . ? O4 Mn1 O1 88.46(8) . . ? O3 Mn1 O1 94.92(9) . . ? O2 Mn1 N3 96.35(9) . . ? O4 Mn1 N3 93.82(9) . . ? O3 Mn1 N3 90.77(9) . . ? O1 Mn1 N3 174.11(9) . . ? O2 Mn1 N1 92.10(9) . . ? O4 Mn1 N1 97.90(8) . . ? O3 Mn1 N1 174.29(9) . . ? O1 Mn1 N1 90.79(9) . . ? N3 Mn1 N1 83.52(9) . . ? C14 O4 Mn1 130.96(19) . . ? C12 O3 Mn1 130.5(2) . . ? C4 O2 Mn1 130.1(2) . . ? C2 O1 Mn1 130.0(2) . . ? C27 N3 C31 117.0(3) . . ? C27 N3 Mn1 129.7(2) . . ? C31 N3 Mn1 113.3(2) . . ? C21 N1 C25 117.4(3) . . ? C21 N1 Mn1 127.8(2) . . ? C25 N1 Mn1 114.9(2) . . ? O3 C12 C13 125.2(3) . . ? O3 C12 C11 116.7(3) . . ? C13 C12 C11 118.1(3) . . ? C21 N2 H34 125(3) . . ? C21 N2 H33 122(3) . . ? H34 N2 H33 106(4) . . ? C30 C31 N3 125.8(3) . . ? C30 C31 H31 117.1 . . ? N3 C31 H31 117.1 . . ? O4 C14 C13 123.7(3) . . ? O4 C14 C15 116.8(3) . . ? C13 C14 C15 119.6(3) . . ? O2 C4 C3 123.8(3) . . ? O2 C4 C5 116.6(3) . . ? C3 C4 C5 119.5(3) . . ? O1 C2 C3 124.8(3) . . ? O1 C2 C1 116.7(3) . . ? C3 C2 C1 118.4(3) . . ? N1 C25 C24 125.5(4) . . ? N1 C25 H25 117.3 . . ? C24 C25 H25 117.3 . . ? N3 C27 N4 117.9(3) . . ? N3 C27 C28 120.5(3) . . ? N4 C27 C28 121.6(3) . . ? C16 C15 C20 115.9(3) . . ? C16 C15 C14 120.7(3) . . ? C20 C15 C14 123.3(3) . . ? N2 C21 N1 118.2(3) . . ? N2 C21 C22 120.7(4) . . ? N1 C21 C22 121.1(3) . . ? C31 C30 C29 115.9(3) . . ? C31 C30 C32 121.7(4) . . ? C29 C30 C32 122.4(4) . . ? C29 C28 C27 120.3(3) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C14 C13 C12 127.1(3) . . ? C14 C13 H13 116.4 . . ? C12 C13 H13 116.4 . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C19 C20 C15 121.7(4) . . ? C19 C20 H20 119.2 . . ? C15 C20 H20 119.2 . . ? C23 C22 C21 119.8(4) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C7 C6 C5 120.8(4) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C10 C5 C6 118.8(4) . . ? C10 C5 C4 120.9(4) . . ? C6 C5 C4 120.3(3) . . ? C4 C3 C2 126.8(3) . . ? C4 C3 H3 116.6 . . ? C2 C3 H3 116.6 . . ? C25 C24 C23 115.3(4) . . ? C25 C24 C26 121.0(4) . . ? C23 C24 C26 123.6(4) . . ? C15 C16 C17 122.2(4) . . ? C15 C16 H16 118.9 . . ? C17 C16 H16 118.9 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C19 C18 C17 119.1(4) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C28 C29 C30 120.6(3) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C22 C23 C24 120.9(4) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C6 C7 C8 120.0(5) . . ? C6 C7 H7 120 . . ? C8 C7 H7 120 . . ? C18 C19 C20 121.0(4) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C18 C17 C16 120.1(4) . . ? C18 C17 H17 120 . . ? C16 C17 H17 120 . . ? C9 C8 C7 119.6(4) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C5 C10 C9 120.1(5) . . ? C5 C10 H10 120 . . ? C9 C10 H10 120 . . ? C8 C9 C10 120.7(4) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C27 N4 H35 122(3) . . ? C27 N4 H36 115(4) . . ? H35 N4 H36 116(5) . . ? _database_code_depnum_ccdc_archive 'CCDC 938360' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2AmPy _audit_creation_date 2012-09-18T18:45:47-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; cis-bis(benzoylacetonato)bis(2-aminopyridine)manganese(II) ; _chemical_formula_sum 'C30 H30 Mn N4 O4' _chemical_formula_moiety 'C30 H30 Mn N4 O4' _chemical_formula_weight 565.52 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0001(7) _cell_length_b 12.7277(10) _cell_length_c 14.1367(14) _cell_angle_alpha 66.042(9) _cell_angle_beta 76.101(7) _cell_angle_gamma 73.393(7) _cell_volume 1403.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2230 _cell_measurement_theta_min 3.762 _cell_measurement_theta_max 38.6781 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 590 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.512 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 295(2) _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur CCD diffractometer ; _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_unetI/netI 0.108 _diffrn_reflns_number 7777 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.966 _diffrn_measured_fraction_theta_max 0.966 _reflns_number_total 4790 _reflns_number_gt 2409 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_cell_refinement ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_data_reduction ; CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003) ; _computing_structure_solution ; 'SIR-92 (Altomare, Cascanaro, Giacovazzo, Gualardi, 1993)' ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material ; WinGX (Farrugia, 1999) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0267P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4790 _refine_ls_number_parameters 370 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0908 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0677 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 0.731 _refine_ls_restrained_S_all 0.732 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.219 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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_ _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 0.54759(5) 0.50977(4) 0.74032(3) 0.04662(15) Uani 1 1 d . . . O2 O 0.4686(2) 0.66142(16) 0.78648(13) 0.0498(5) Uani 1 1 d . . . O4 O 0.6682(2) 0.37179(15) 0.68163(12) 0.0517(5) Uani 1 1 d . . . O3 O 0.7605(2) 0.45822(16) 0.81044(12) 0.0507(5) Uani 1 1 d . . . O1 O 0.6297(2) 0.64041(17) 0.59389(13) 0.0501(5) Uani 1 1 d . . . N1 N 0.3133(2) 0.54343(19) 0.67867(15) 0.0460(6) Uani 1 1 d U . . N3 N 0.4318(3) 0.3824(2) 0.89664(16) 0.0482(6) Uani 1 1 d . . . C2 C 0.6238(3) 0.7481(3) 0.5712(2) 0.0513(8) Uani 1 1 d U . . C12 C 0.8789(3) 0.3760(3) 0.8090(2) 0.0482(7) Uani 1 1 d . . . C22 C 0.0486(4) 0.6544(3) 0.6809(3) 0.0754(10) Uani 1 1 d . . . H22 H -0.0292 0.7089 0.7032 0.09 Uiso 1 1 calc R . . C26 C 0.4516(4) 0.2717(3) 0.8995(2) 0.0625(9) Uani 1 1 d . . . H26 H 0.5095 0.255 0.8413 0.075 Uiso 1 1 calc R . . C25 C 0.2814(4) 0.4946(3) 0.6204(2) 0.0534(8) Uani 1 1 d U . . C21 C 0.1951(3) 0.6223(2) 0.7077(2) 0.0596(8) Uani 1 1 d . . . H21 H 0.215 0.657 0.7487 0.072 Uiso 1 1 calc R . . C30 C 0.3464(3) 0.4043(3) 0.9806(2) 0.0524(8) Uani 1 1 d . . . C4 C 0.4762(3) 0.7687(3) 0.7372(2) 0.0454(7) Uani 1 1 d . . . C11 C 1.0078(3) 0.3617(2) 0.8679(2) 0.0667(9) Uani 1 1 d . . . H11A H 1.029 0.4373 0.8519 0.1 Uiso 1 1 calc R . . H11B H 1.1009 0.3115 0.8474 0.1 Uiso 1 1 calc R . . H11C H 0.9752 0.3272 0.9417 0.1 Uiso 1 1 calc R . . N4 N 0.3227(4) 0.5142(3) 0.9804(2) 0.0731(9) Uani 1 1 d . . . C24 C 0.1335(4) 0.5246(3) 0.5891(2) 0.0714(10) Uani 1 1 d . . . H24 H 0.1147 0.4902 0.5475 0.086 Uiso 1 1 calc R . . C3 C 0.5516(3) 0.8123(2) 0.6360(2) 0.0537(8) Uani 1 1 d U . . H5 H 0.5543 0.8917 0.6087 0.064 Uiso 1 1 calc R . . C5 C 0.3933(3) 0.8521(2) 0.7932(2) 0.0468(7) Uani 1 1 d . . . N2 N 0.3923(4) 0.4114(3) 0.5943(3) 0.0889(11) Uani 1 1 d . . . C29 C 0.2804(4) 0.3181(3) 1.0663(2) 0.0701(9) Uani 1 1 d U . . H29 H 0.2205 0.3359 1.1235 0.084 Uiso 1 1 calc R . . C27 C 0.3944(4) 0.1831(3) 0.9797(3) 0.0730(10) Uani 1 1 d . . . H27 H 0.4143 0.1081 0.9778 0.088 Uiso 1 1 calc R . . C13 C 0.8988(3) 0.2960(2) 0.7595(2) 0.0532(8) Uani 1 1 d . . . H13 H 0.9917 0.2395 0.7647 0.064 Uiso 1 1 calc R . . C1 C 0.7031(4) 0.8122(3) 0.4629(2) 0.0795(10) Uani 1 1 d . . . H1A H 0.6584 0.8053 0.411 0.119 Uiso 1 1 calc R . . H1B H 0.8132 0.7779 0.457 0.119 Uiso 1 1 calc R . . H1C H 0.6878 0.8938 0.4524 0.119 Uiso 1 1 calc R . . C14 C 0.7934(3) 0.2928(2) 0.70362(19) 0.0456(7) Uani 1 1 d . . . C15 C 0.8215(3) 0.1914(2) 0.6695(2) 0.0484(7) Uani 1 1 d U . . C6 C 0.2751(4) 0.8220(3) 0.8748(2) 0.0659(9) Uani 1 1 d . . . H6 H 0.2478 0.75 0.8946 0.079 Uiso 1 1 calc R . . C8 C 0.2334(4) 1.0032(3) 0.8992(3) 0.0772(10) Uani 1 1 d . . . H8 H 0.1802 1.0537 0.9348 0.093 Uiso 1 1 calc R . . C10 C 0.4297(4) 0.9599(3) 0.7659(2) 0.0617(9) Uani 1 1 d . . . H10 H 0.5099 0.982 0.7116 0.074 Uiso 1 1 calc R . . C9 C 0.3492(4) 1.0356(3) 0.8180(2) 0.0709(10) Uani 1 1 d . . . H9 H 0.374 1.1085 0.7976 0.085 Uiso 1 1 calc R . . C7 C 0.1957(4) 0.8971(3) 0.9282(3) 0.0813(10) Uani 1 1 d . . . H7 H 0.117 0.8748 0.9837 0.098 Uiso 1 1 calc R . . C28 C 0.3049(4) 0.2097(3) 1.0649(3) 0.0770(10) Uani 1 1 d U . . H28 H 0.2615 0.152 1.1212 0.092 Uiso 1 1 calc R . . C23 C 0.0191(4) 0.6036(3) 0.6198(3) 0.0814(11) Uani 1 1 d . . . H23 H -0.0796 0.6238 0.5999 0.098 Uiso 1 1 calc R . . C16 C 0.7502(3) 0.2028(3) 0.5881(2) 0.0579(8) Uani 1 1 d . . . H16 H 0.6868 0.2744 0.5541 0.069 Uiso 1 1 calc R . . C18 C 0.8639(4) 0.0028(3) 0.6061(3) 0.0756(10) Uani 1 1 d . . . H18 H 0.8774 -0.0602 0.5852 0.091 Uiso 1 1 calc R . . C20 C 0.9141(3) 0.0835(3) 0.7173(2) 0.0692(9) Uani 1 1 d U . . H20 H 0.9633 0.0737 0.7721 0.083 Uiso 1 1 calc R . . C17 C 0.7724(4) 0.1090(3) 0.5569(2) 0.0688(9) Uani 1 1 d . . . H17 H 0.7243 0.1182 0.5018 0.083 Uiso 1 1 calc R . . C19 C 0.9360(4) -0.0103(3) 0.6865(3) 0.0809(10) Uani 1 1 d . . . H19 H 0.9994 -0.082 0.7201 0.097 Uiso 1 1 calc R . . H3 H 0.301(3) 0.526(2) 1.041(2) 0.075(10) Uiso 1 1 d . . . H1 H 0.479(3) 0.393(2) 0.612(2) 0.060(10) Uiso 1 1 d . . . H4 H 0.387(4) 0.571(3) 0.935(3) 0.139(17) Uiso 1 1 d . . . H2 H 0.387(3) 0.391(3) 0.542(2) 0.095(12) 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 0.0456(3) 0.0485(3) 0.0492(3) -0.0245(2) -0.0063(2) -0.0054(2) O2 0.0587(13) 0.0402(13) 0.0502(12) -0.0209(11) 0.0015(10) -0.0111(10) O4 0.0445(12) 0.0564(14) 0.0577(12) -0.0321(11) -0.0139(10) 0.0067(10) O3 0.0450(13) 0.0596(14) 0.0519(11) -0.0292(11) -0.0070(10) -0.0042(10) O1 0.0524(13) 0.0539(14) 0.0465(11) -0.0233(11) -0.0062(9) -0.0080(11) N1 0.0407(15) 0.0533(16) 0.0454(13) -0.0220(12) -0.0070(11) -0.0054(12) N3 0.0513(16) 0.0504(18) 0.0465(14) -0.0224(14) -0.0070(12) -0.0088(12) C2 0.047(2) 0.055(2) 0.0437(18) -0.0114(18) -0.0098(15) -0.0066(17) C12 0.044(2) 0.048(2) 0.0482(17) -0.0136(16) -0.0046(15) -0.0118(15) C22 0.043(2) 0.069(3) 0.093(3) -0.019(2) -0.0059(19) 0.0013(17) C26 0.071(2) 0.059(3) 0.063(2) -0.026(2) -0.0046(18) -0.0215(19) C25 0.053(2) 0.064(2) 0.0458(18) -0.0197(16) -0.0100(16) -0.0139(16) C21 0.046(2) 0.057(2) 0.072(2) -0.0236(18) -0.0022(17) -0.0101(16) C30 0.051(2) 0.058(2) 0.0471(19) -0.0186(19) -0.0101(16) -0.0082(17) C4 0.0479(19) 0.043(2) 0.0479(18) -0.0160(17) -0.0140(15) -0.0090(15) C11 0.058(2) 0.074(2) 0.072(2) -0.0252(19) -0.0232(17) -0.0111(17) N4 0.104(3) 0.065(2) 0.0508(18) -0.0306(18) 0.0064(17) -0.0190(18) C24 0.059(2) 0.093(3) 0.066(2) -0.020(2) -0.0255(19) -0.024(2) C3 0.069(2) 0.042(2) 0.0459(17) -0.0153(16) -0.0038(16) -0.0097(15) C5 0.058(2) 0.039(2) 0.0432(17) -0.0153(16) -0.0105(15) -0.0073(15) N2 0.068(2) 0.126(3) 0.109(3) -0.087(2) -0.032(2) 0.007(2) C29 0.077(2) 0.078(2) 0.0459(18) -0.010(2) -0.0030(17) -0.026(2) C27 0.088(3) 0.058(3) 0.078(2) -0.020(2) -0.021(2) -0.022(2) C13 0.0423(18) 0.047(2) 0.0674(19) -0.0227(17) -0.0117(15) 0.0008(14) C1 0.097(3) 0.071(3) 0.0503(19) -0.0093(19) 0.0004(19) -0.015(2) C14 0.0424(18) 0.044(2) 0.0438(16) -0.0150(15) 0.0012(14) -0.0069(14) C15 0.0435(18) 0.0459(18) 0.0525(18) -0.0202(15) 0.0029(14) -0.0092(12) C6 0.067(2) 0.054(2) 0.080(2) -0.035(2) 0.0056(19) -0.0135(18) C8 0.088(3) 0.067(3) 0.077(3) -0.041(2) -0.013(2) 0.006(2) C10 0.082(2) 0.051(2) 0.0490(18) -0.0161(18) -0.0086(16) -0.0137(18) C9 0.102(3) 0.051(2) 0.066(2) -0.026(2) -0.020(2) -0.012(2) C7 0.077(3) 0.068(3) 0.098(3) -0.046(2) 0.015(2) -0.012(2) C28 0.087(3) 0.077(2) 0.064(2) -0.006(2) -0.018(2) -0.035(2) C23 0.047(2) 0.090(3) 0.085(3) 0.000(2) -0.025(2) -0.016(2) C16 0.058(2) 0.053(2) 0.0600(19) -0.0270(18) -0.0036(16) -0.0028(16) C18 0.077(3) 0.057(3) 0.096(3) -0.042(2) 0.008(2) -0.016(2) C20 0.073(2) 0.050(2) 0.084(2) -0.0264(19) -0.0206(18) -0.0004(15) C17 0.076(3) 0.070(3) 0.067(2) -0.039(2) -0.0012(18) -0.013(2) C19 0.083(3) 0.049(2) 0.106(3) -0.030(2) -0.026(2) 0.0054(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O4 2.1476(16) . ? Mn1 O2 2.1616(17) . ? Mn1 O3 2.1792(17) . ? Mn1 O1 2.184(2) . ? Mn1 N1 2.335(2) . ? Mn1 N3 2.355(2) . ? O2 C4 1.270(3) . ? O4 C14 1.282(3) . ? O3 C12 1.265(3) . ? O1 C2 1.263(3) . ? N1 C25 1.334(3) . ? N1 C21 1.350(3) . ? N3 C30 1.336(3) . ? N3 C26 1.354(3) . ? C2 C3 1.395(3) . ? C2 C1 1.520(4) . ? C12 C13 1.404(3) . ? C12 C11 1.514(3) . ? C22 C21 1.362(4) . ? C22 C23 1.377(4) . ? C22 H22 0.93 . ? C26 C27 1.355(4) . ? C26 H26 0.93 . ? C25 N2 1.338(4) . ? C25 C24 1.404(4) . ? C21 H21 0.93 . ? C30 N4 1.351(3) . ? C30 C29 1.405(4) . ? C4 C3 1.386(3) . ? C4 C5 1.502(3) . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? N4 H3 0.89(3) . ? N4 H4 0.97(4) . ? C24 C23 1.344(4) . ? C24 H24 0.93 . ? C3 H5 0.93 . ? C5 C6 1.376(4) . ? C5 C10 1.380(3) . ? N2 H1 0.82(2) . ? N2 H2 0.89(3) . ? C29 C28 1.342(4) . ? C29 H29 0.93 . ? C27 C28 1.386(4) . ? C27 H27 0.93 . ? C13 C14 1.391(3) . ? C13 H13 0.93 . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C14 C15 1.491(3) . ? C15 C20 1.378(3) . ? C15 C16 1.386(3) . ? C6 C7 1.389(3) . ? C6 H6 0.93 . ? C8 C7 1.362(4) . ? C8 C9 1.364(4) . ? C8 H8 0.93 . ? C10 C9 1.384(3) . ? C10 H10 0.93 . ? C9 H9 0.93 . ? C7 H7 0.93 . ? C28 H28 0.93 . ? C23 H23 0.93 . ? C16 C17 1.382(3) . ? C16 H16 0.93 . ? C18 C17 1.366(4) . ? C18 C19 1.371(4) . ? C18 H18 0.93 . ? C20 C19 1.379(4) . ? C20 H20 0.93 . ? C17 H17 0.93 . ? C19 H19 0.93 . ? 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 Mn1 O2 168.63(7) . . ? O4 Mn1 O3 82.19(6) . . ? O2 Mn1 O3 90.71(6) . . ? O4 Mn1 O1 90.32(7) . . ? O2 Mn1 O1 81.59(7) . . ? O3 Mn1 O1 96.17(7) . . ? O4 Mn1 N1 95.24(7) . . ? O2 Mn1 N1 92.76(7) . . ? O3 Mn1 N1 173.23(8) . . ? O1 Mn1 N1 90.09(7) . . ? O4 Mn1 N3 93.91(8) . . ? O2 Mn1 N3 94.83(8) . . ? O3 Mn1 N3 88.96(7) . . ? O1 Mn1 N3 173.75(8) . . ? N1 Mn1 N3 84.96(7) . . ? C4 O2 Mn1 132.03(16) . . ? C14 O4 Mn1 131.58(15) . . ? C12 O3 Mn1 129.78(16) . . ? C2 O1 Mn1 129.91(17) . . ? C25 N1 C21 116.7(2) . . ? C25 N1 Mn1 128.76(19) . . ? C21 N1 Mn1 114.58(16) . . ? C30 N3 C26 115.9(3) . . ? C30 N3 Mn1 129.7(2) . . ? C26 N3 Mn1 114.39(19) . . ? O1 C2 C3 126.0(3) . . ? O1 C2 C1 116.1(3) . . ? C3 C2 C1 117.9(3) . . ? O3 C12 C13 125.5(2) . . ? O3 C12 C11 116.8(2) . . ? C13 C12 C11 117.7(2) . . ? C21 C22 C23 118.0(3) . . ? C21 C22 H22 121 . . ? C23 C22 H22 121 . . ? N3 C26 C27 125.6(3) . . ? N3 C26 H26 117.2 . . ? C27 C26 H26 117.2 . . ? N1 C25 N2 118.9(3) . . ? N1 C25 C24 122.0(3) . . ? N2 C25 C24 119.1(3) . . ? N1 C21 C22 124.3(3) . . ? N1 C21 H21 117.9 . . ? C22 C21 H21 117.9 . . ? N3 C30 N4 117.7(3) . . ? N3 C30 C29 122.1(3) . . ? N4 C30 C29 120.2(3) . . ? O2 C4 C3 124.2(3) . . ? O2 C4 C5 116.6(2) . . ? C3 C4 C5 119.2(3) . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C30 N4 H3 119.7(18) . . ? C30 N4 H4 124(2) . . ? H3 N4 H4 104(3) . . ? C23 C24 C25 119.4(3) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C4 C3 C2 126.1(3) . . ? C4 C3 H5 116.9 . . ? C2 C3 H5 116.9 . . ? C6 C5 C10 117.6(3) . . ? C6 C5 C4 119.7(3) . . ? C10 C5 C4 122.7(3) . . ? C25 N2 H1 120.5(18) . . ? C25 N2 H2 121(2) . . ? H1 N2 H2 115(3) . . ? C28 C29 C30 119.2(3) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C26 C27 C28 116.8(3) . . ? C26 C27 H27 121.6 . . ? C28 C27 H27 121.6 . . ? C14 C13 C12 126.5(2) . . ? C14 C13 H13 116.8 . . ? C12 C13 H13 116.8 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O4 C14 C13 123.4(2) . . ? O4 C14 C15 117.0(2) . . ? C13 C14 C15 119.6(2) . . ? C20 C15 C16 117.4(3) . . ? C20 C15 C14 122.6(2) . . ? C16 C15 C14 119.9(2) . . ? C5 C6 C7 121.3(3) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C7 C8 C9 120.0(3) . . ? C7 C8 H8 120 . . ? C9 C8 H8 120 . . ? C5 C10 C9 121.3(3) . . ? C5 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 120 . . ? C10 C9 H9 120 . . ? C8 C7 C6 119.9(3) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C29 C28 C27 120.3(3) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C24 C23 C22 119.7(3) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C17 C16 C15 120.7(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C17 C18 C19 119.5(3) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C15 C20 C19 122.0(3) . . ? C15 C20 H20 119 . . ? C19 C20 H20 119 . . ? C18 C17 C16 120.8(3) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C18 C19 C20 119.7(3) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 938361'