#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:10:52 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257959 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240440.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7240440 loop_ _publ_author_name 'Rayati, Saeed' 'Khodaei, Elham' 'Nafarieh, Parinaz' 'Jafarian, Majid' 'Elmi, Bahareh' 'Wojtczak, Andrzej' _publ_section_title ; A manganese(iii) Schiff base complex immobilized on silica-coated magnetic nanoparticles showing enhanced electrochemical catalytic performance toward sulfide and alkene oxidation ; _journal_issue 29 _journal_name_full 'RSC Advances' _journal_page_first 17026 _journal_page_last 17036 _journal_paper_doi 10.1039/D0RA02728F _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C23 H27 Mn N2 O6' _chemical_formula_sum 'C23 H27 Mn N2 O6' _chemical_formula_weight 482.40 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2020-01-13 deposited with the CCDC. 2020-04-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.859(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.1400(9) _cell_length_b 12.8784(12) _cell_length_c 19.5628(19) _cell_measurement_reflns_used 6094 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.8450 _cell_measurement_theta_min 2.6110 _cell_volume 2290.7(4) _computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_publication_material 'CIFTAB-2017 (Sheldrick, 2017)' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXS 2017/1 (Sheldrick, 2017)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.2564 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.886 _diffrn_measurement_device_type 'Oxford Sapphire CCD' _diffrn_measurement_method \q/2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_unetI/netI 0.0412 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.886 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 15348 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.886 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.656 _diffrn_reflns_theta_min 2.240 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.617 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_correction_T_min 0.747 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.399 _exptl_crystal_description plate _exptl_crystal_F_000 1008 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH2Cl2 - MeOH' _exptl_crystal_size_max 0.611 _exptl_crystal_size_mid 0.411 _exptl_crystal_size_min 0.146 _refine_diff_density_max 0.379 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.127 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 5222 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0418 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.6899P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0949 _refine_ls_wR_factor_ref 0.1020 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4172 _reflns_number_total 5222 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02728f2.cif _cod_data_source_block e1375a _cod_depositor_comments 'Adding full bibliography for 7240440.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240440 _shelx_shelxl_version_number 2017/1 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.704 _shelx_estimated_absorpt_t_max 0.915 _exptl_absorpt_special_details ; CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _shelx_res_file ; TITL e1375a in P2(1)/c e1375a.res created by SHELXL-2017/1 at 18:29:58 on 29-Jul-2019 REM P2(1)/c (#14 in standard setting) CELL 0.71073 9.140049 12.878420 19.562820 90.0000 95.8593 90.0000 ZERR 4.00 0.000940 0.001229 0.001925 0.0000 0.0108 0.0000 LATT 1 SYMM -x, y+1/2,-z+1/2 SFAC C H N O Mn UNIT 92.00 108.00 8.00 24.00 4.00 TEMP 20 SIZE 0.611 0.411 0.146 L.S. 15 BOND $H FMAP 2 PLAN 10 OMIT -3 OMIT 0 0 2 CONF HTAB EQIV $1 -x+1, -y, -z+1 EQIV $2 -x+1, y+1/2, -z+1/2 HTAB C7 O5_$1 HTAB C10 O5 HTAB C18 O6_$2 HTAB C21 O2 ACTA WGHT 0.043600 0.689900 FVAR 2.68738 MOLE 1 MN1 5 0.427569 0.010524 0.334451 11.00000 0.03328 0.02762 = 0.02765 0.00030 0.00717 0.00347 O1 4 0.393520 0.140610 0.371365 11.00000 0.04166 0.02892 = 0.04250 -0.00080 0.01718 0.00263 C1 1 0.279083 0.161871 0.404819 11.00000 0.03267 0.02894 = 0.02981 -0.00486 0.00319 0.00002 C2 1 0.218649 0.263537 0.398436 11.00000 0.04144 0.03035 = 0.04046 -0.00323 0.00848 0.00062 C3 1 0.104761 0.291378 0.434946 11.00000 0.05195 0.03646 = 0.06063 -0.00610 0.01704 0.01061 AFIX 43 H3A 2 0.063422 0.357144 0.428928 11.00000 -1.20000 AFIX 0 C4 1 0.050078 0.222692 0.480884 11.00000 0.05120 0.04748 = 0.06919 -0.00936 0.03130 0.00578 AFIX 43 H4A 2 -0.025888 0.243101 0.506120 11.00000 -1.20000 AFIX 0 C5 1 0.108279 0.124792 0.488952 11.00000 0.04663 0.04198 = 0.04687 -0.00615 0.02127 -0.00341 AFIX 43 H5A 2 0.072899 0.079717 0.520567 11.00000 -1.20000 AFIX 0 C6 1 0.220256 0.091787 0.450229 11.00000 0.03455 0.03223 = 0.03059 -0.00604 0.00506 -0.00157 C7 1 0.280183 -0.011377 0.462842 11.00000 0.03794 0.03452 = 0.02492 -0.00170 0.00520 -0.00547 AFIX 43 H7A 2 0.252363 -0.046584 0.500956 11.00000 -1.20000 AFIX 0 N1 3 0.367509 -0.058305 0.426509 11.00000 0.03382 0.02862 = 0.02779 -0.00151 0.00107 0.00055 C8 1 0.431336 -0.157395 0.452107 11.00000 0.04196 0.03482 = 0.03130 0.00301 -0.00279 0.00429 AFIX 23 H8A 2 0.375933 -0.182366 0.488519 11.00000 -1.20000 H8B 2 0.531435 -0.145025 0.471975 11.00000 -1.20000 AFIX 0 C9 1 0.433293 -0.242498 0.397468 11.00000 0.03373 0.02778 = 0.03600 0.00222 0.00241 0.00337 C10 1 0.527830 -0.210436 0.340325 11.00000 0.03246 0.03145 = 0.04668 0.00123 0.00709 0.00611 AFIX 23 H10A 2 0.622158 -0.185553 0.361201 11.00000 -1.20000 H10B 2 0.545835 -0.271089 0.313002 11.00000 -1.20000 AFIX 0 N2 3 0.459481 -0.129111 0.294699 11.00000 0.03244 0.02941 = 0.03304 -0.00015 0.00698 0.00221 C11 1 0.423915 -0.150647 0.230602 11.00000 0.04141 0.03312 = 0.04083 -0.00551 0.01498 -0.00148 AFIX 43 H11A 2 0.457525 -0.213319 0.214492 11.00000 -1.20000 AFIX 0 C12 1 0.336553 -0.085945 0.181780 11.00000 0.03880 0.04014 = 0.03199 -0.00247 0.00701 -0.00746 C13 1 0.325178 -0.112568 0.111499 11.00000 0.05492 0.05155 = 0.03696 -0.00871 0.01282 -0.01032 AFIX 43 H13A 2 0.381234 -0.166957 0.096874 11.00000 -1.20000 AFIX 0 C14 1 0.232051 -0.058927 0.064379 11.00000 0.05774 0.07030 = 0.03042 -0.00411 0.00303 -0.01771 AFIX 43 H14A 2 0.227563 -0.075266 0.017906 11.00000 -1.20000 AFIX 0 C15 1 0.145071 0.019562 0.086686 11.00000 0.04184 0.06554 = 0.03976 0.01041 -0.00531 -0.01459 AFIX 43 H15A 2 0.081162 0.054986 0.054761 11.00000 -1.20000 AFIX 0 C16 1 0.150911 0.046418 0.154955 11.00000 0.03006 0.05229 = 0.04080 0.00552 0.00210 -0.00790 C17 1 0.249878 -0.004310 0.204815 11.00000 0.02996 0.04300 = 0.03307 0.00082 0.00539 -0.00599 O2 4 0.254263 0.022256 0.270187 11.00000 0.03779 0.05205 = 0.03314 -0.00411 0.00411 0.01044 O3 4 0.283398 0.326745 0.354559 11.00000 0.06577 0.02879 = 0.06052 0.00611 0.02589 0.00806 C18 1 0.235467 0.431529 0.349530 11.00000 0.11787 0.03662 = 0.11240 0.02008 0.06034 0.02141 AFIX 33 H18A 2 0.289071 0.467773 0.317186 11.00000 -1.20000 H18B 2 0.132292 0.433510 0.334269 11.00000 -1.20000 H18C 2 0.252613 0.464188 0.393735 11.00000 -1.20000 AFIX 0 C19 1 0.277306 -0.269565 0.367329 11.00000 0.03812 0.03952 = 0.05024 -0.00476 0.00662 -0.00597 AFIX 33 H19A 2 0.281055 -0.322917 0.333281 11.00000 -1.20000 H19B 2 0.221908 -0.293902 0.403269 11.00000 -1.20000 H19C 2 0.230855 -0.208898 0.346485 11.00000 -1.20000 AFIX 0 C20 1 0.510191 -0.337357 0.432700 11.00000 0.05532 0.03812 = 0.05744 0.01075 0.00903 0.01293 AFIX 33 H20A 2 0.607892 -0.318501 0.451218 11.00000 -1.20000 H20B 2 0.455538 -0.360702 0.469166 11.00000 -1.20000 H20C 2 0.515170 -0.392113 0.399719 11.00000 -1.20000 AFIX 0 O4 4 0.051489 0.117857 0.173947 11.00000 0.03485 0.06248 = 0.06133 0.00417 -0.00071 0.00427 C21 1 0.109084 0.210235 0.205050 11.00000 0.04280 0.05982 = 0.09700 0.00451 0.01359 0.00293 AFIX 33 H21A 2 0.029697 0.253968 0.216025 11.00000 -1.20000 H21B 2 0.170437 0.193496 0.246364 11.00000 -1.20000 H21C 2 0.166241 0.245992 0.173889 11.00000 -1.20000 AFIX 0 O5 4 0.652559 0.013017 0.373335 11.00000 0.04673 0.04825 = 0.03488 0.00280 0.00895 -0.00429 O6 4 0.599921 0.081574 0.271519 11.00000 0.05064 0.04657 = 0.03932 0.00382 0.00526 -0.00053 C22 1 0.693025 0.060023 0.321209 11.00000 0.03966 0.04648 = 0.03758 -0.00360 0.01270 -0.00584 C23 1 0.850858 0.088810 0.321077 11.00000 0.05070 0.13168 = 0.05860 0.00418 0.01108 -0.03311 AFIX 33 H23A 2 0.904604 0.066023 0.363126 11.00000 -1.20000 H23B 2 0.890337 0.056136 0.282850 11.00000 -1.20000 H23C 2 0.859342 0.162823 0.317169 11.00000 -1.20000 AFIX 0 HKLF 4 REM e1375a in P2(1)/c REM R1 = 0.0418 for 4172 Fo > 4sig(Fo) and 0.0591 for all 5222 data REM 289 parameters refined using 0 restraints END WGHT 0.0436 0.6899 REM Instructions for potential hydrogen bonds HTAB C7 O5_$1 HTAB C10 O5 HTAB C18 O6_$2 HTAB C21 O2 REM Highest difference peak 0.379, deepest hole -0.416, 1-sigma level 0.127 Q1 1 0.8871 0.0060 0.3199 11.00000 0.05 0.38 Q2 1 0.8932 0.1369 0.3672 11.00000 0.05 0.35 Q3 1 0.8763 0.1247 0.2716 11.00000 0.05 0.34 Q4 1 0.0905 0.2387 0.1437 11.00000 0.05 0.33 Q5 1 0.0643 0.1753 0.4831 11.00000 0.05 0.32 Q6 1 0.0660 0.2630 0.1771 11.00000 0.05 0.30 Q7 1 0.0847 0.1977 0.2794 11.00000 0.05 0.30 Q8 1 0.0019 0.1355 0.1316 11.00000 0.05 0.30 Q9 1 0.9497 0.0358 0.4291 11.00000 0.05 0.30 Q10 1 0.0273 0.0285 0.2015 11.00000 0.05 0.30 ; _shelx_res_checksum 47557 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.42757(3) 0.01052(2) 0.33445(2) 0.02924(10) Uani 1 1 d . . . . . O1 O 0.39352(16) 0.14061(10) 0.37136(7) 0.0368(3) Uani 1 1 d . . . . . C1 C 0.2791(2) 0.16187(15) 0.40482(10) 0.0305(4) Uani 1 1 d . . . . . C2 C 0.2186(2) 0.26354(16) 0.39844(11) 0.0371(5) Uani 1 1 d . . . . . C3 C 0.1048(3) 0.29138(18) 0.43495(13) 0.0489(6) Uani 1 1 d . . . . . H3A H 0.063422 0.357144 0.428928 0.059 Uiso 1 1 calc R U . . . C4 C 0.0501(3) 0.22269(19) 0.48088(14) 0.0542(7) Uani 1 1 d . . . . . H4A H -0.025888 0.243101 0.506120 0.065 Uiso 1 1 calc R U . . . C5 C 0.1083(3) 0.12479(18) 0.48895(12) 0.0440(5) Uani 1 1 d . . . . . H5A H 0.072899 0.079717 0.520567 0.053 Uiso 1 1 calc R U . . . C6 C 0.2203(2) 0.09179(15) 0.45023(10) 0.0323(4) Uani 1 1 d . . . . . C7 C 0.2802(2) -0.01138(15) 0.46284(10) 0.0323(4) Uani 1 1 d . . . . . H7A H 0.252363 -0.046584 0.500956 0.039 Uiso 1 1 calc R U . . . N1 N 0.36751(18) -0.05830(12) 0.42651(8) 0.0302(4) Uani 1 1 d . . . . . C8 C 0.4313(2) -0.15739(16) 0.45211(11) 0.0365(5) Uani 1 1 d . . . . . H8A H 0.375933 -0.182366 0.488519 0.044 Uiso 1 1 calc R U . . . H8B H 0.531435 -0.145025 0.471975 0.044 Uiso 1 1 calc R U . . . C9 C 0.4333(2) -0.24250(15) 0.39747(10) 0.0326(4) Uani 1 1 d . . . . . C10 C 0.5278(2) -0.21044(16) 0.34033(11) 0.0367(5) Uani 1 1 d . . . . . H10A H 0.622158 -0.185553 0.361201 0.044 Uiso 1 1 calc R U . . . H10B H 0.545835 -0.271089 0.313002 0.044 Uiso 1 1 calc R U . . . N2 N 0.45948(18) -0.12911(12) 0.29470(9) 0.0314(4) Uani 1 1 d . . . . . C11 C 0.4239(2) -0.15065(16) 0.23060(11) 0.0377(5) Uani 1 1 d . . . . . H11A H 0.457525 -0.213319 0.214492 0.045 Uiso 1 1 calc R U . . . C12 C 0.3366(2) -0.08594(17) 0.18178(11) 0.0367(5) Uani 1 1 d . . . . . C13 C 0.3252(3) -0.11257(19) 0.11150(12) 0.0472(6) Uani 1 1 d . . . . . H13A H 0.381234 -0.166957 0.096874 0.057 Uiso 1 1 calc R U . . . C14 C 0.2321(3) -0.0589(2) 0.06438(12) 0.0529(7) Uani 1 1 d . . . . . H14A H 0.227563 -0.075266 0.017906 0.064 Uiso 1 1 calc R U . . . C15 C 0.1451(3) 0.0196(2) 0.08669(12) 0.0497(6) Uani 1 1 d . . . . . H15A H 0.081162 0.054986 0.054761 0.060 Uiso 1 1 calc R U . . . C16 C 0.1509(2) 0.04642(19) 0.15496(12) 0.0412(5) Uani 1 1 d . . . . . C17 C 0.2499(2) -0.00431(16) 0.20481(11) 0.0352(5) Uani 1 1 d . . . . . O2 O 0.25426(16) 0.02226(12) 0.27019(8) 0.0410(4) Uani 1 1 d . . . . . O3 O 0.28340(19) 0.32674(11) 0.35456(9) 0.0504(4) Uani 1 1 d . . . . . C18 C 0.2355(4) 0.4315(2) 0.34953(19) 0.0856(11) Uani 1 1 d . . . . . H18A H 0.289071 0.467773 0.317186 0.103 Uiso 1 1 calc R U . . . H18B H 0.132292 0.433510 0.334269 0.103 Uiso 1 1 calc R U . . . H18C H 0.252613 0.464188 0.393735 0.103 Uiso 1 1 calc R U . . . C19 C 0.2773(2) -0.26956(17) 0.36733(12) 0.0425(5) Uani 1 1 d . . . . . H19A H 0.281055 -0.322917 0.333281 0.051 Uiso 1 1 calc R U . . . H19B H 0.221908 -0.293902 0.403269 0.051 Uiso 1 1 calc R U . . . H19C H 0.230855 -0.208898 0.346485 0.051 Uiso 1 1 calc R U . . . C20 C 0.5102(3) -0.33736(18) 0.43270(13) 0.0501(6) Uani 1 1 d . . . . . H20A H 0.607892 -0.318501 0.451218 0.060 Uiso 1 1 calc R U . . . H20B H 0.455538 -0.360702 0.469166 0.060 Uiso 1 1 calc R U . . . H20C H 0.515170 -0.392113 0.399719 0.060 Uiso 1 1 calc R U . . . O4 O 0.05149(17) 0.11786(14) 0.17395(9) 0.0533(4) Uani 1 1 d . . . . . C21 C 0.1091(3) 0.2102(2) 0.20505(17) 0.0661(8) Uani 1 1 d . . . . . H21A H 0.029697 0.253968 0.216025 0.079 Uiso 1 1 calc R U . . . H21B H 0.170437 0.193496 0.246364 0.079 Uiso 1 1 calc R U . . . H21C H 0.166241 0.245992 0.173889 0.079 Uiso 1 1 calc R U . . . O5 O 0.65256(17) 0.01302(12) 0.37333(8) 0.0430(4) Uani 1 1 d . . . . . O6 O 0.59992(18) 0.08157(12) 0.27152(8) 0.0455(4) Uani 1 1 d . . . . . C22 C 0.6930(2) 0.06002(18) 0.32121(12) 0.0406(5) Uani 1 1 d . . . . . C23 C 0.8509(3) 0.0888(3) 0.32108(16) 0.0799(10) Uani 1 1 d . . . . . H23A H 0.904604 0.066023 0.363126 0.096 Uiso 1 1 calc R U . . . H23B H 0.890337 0.056136 0.282850 0.096 Uiso 1 1 calc R U . . . H23C H 0.859342 0.162823 0.317169 0.096 Uiso 1 1 calc R U . . . 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 0.03328(17) 0.02762(16) 0.02765(17) 0.00030(12) 0.00717(13) 0.00347(12) O1 0.0417(8) 0.0289(7) 0.0425(8) -0.0008(6) 0.0172(7) 0.0026(6) C1 0.0327(10) 0.0289(10) 0.0298(10) -0.0049(8) 0.0032(9) 0.0000(8) C2 0.0414(12) 0.0303(10) 0.0405(12) -0.0032(9) 0.0085(10) 0.0006(9) C3 0.0519(14) 0.0365(12) 0.0606(16) -0.0061(11) 0.0170(13) 0.0106(11) C4 0.0512(14) 0.0475(14) 0.0692(17) -0.0094(12) 0.0313(14) 0.0058(12) C5 0.0466(13) 0.0420(12) 0.0469(13) -0.0061(10) 0.0213(12) -0.0034(10) C6 0.0345(11) 0.0322(10) 0.0306(10) -0.0060(8) 0.0051(9) -0.0016(8) C7 0.0379(11) 0.0345(10) 0.0249(10) -0.0017(8) 0.0052(9) -0.0055(9) N1 0.0338(9) 0.0286(8) 0.0278(8) -0.0015(7) 0.0011(7) 0.0006(7) C8 0.0420(12) 0.0348(11) 0.0313(11) 0.0030(8) -0.0028(10) 0.0043(9) C9 0.0337(11) 0.0278(10) 0.0360(11) 0.0022(8) 0.0024(9) 0.0034(8) C10 0.0325(11) 0.0315(10) 0.0467(13) 0.0012(9) 0.0071(10) 0.0061(9) N2 0.0324(9) 0.0294(8) 0.0330(9) -0.0001(7) 0.0070(8) 0.0022(7) C11 0.0414(12) 0.0331(11) 0.0408(12) -0.0055(9) 0.0150(11) -0.0015(9) C12 0.0388(12) 0.0401(11) 0.0320(11) -0.0025(9) 0.0070(10) -0.0075(9) C13 0.0549(15) 0.0515(14) 0.0370(13) -0.0087(10) 0.0128(12) -0.0103(12) C14 0.0577(15) 0.0703(18) 0.0304(12) -0.0041(11) 0.0030(12) -0.0177(14) C15 0.0418(13) 0.0655(16) 0.0398(13) 0.0104(11) -0.0053(11) -0.0146(12) C16 0.0301(11) 0.0523(13) 0.0408(13) 0.0055(10) 0.0021(10) -0.0079(10) C17 0.0300(10) 0.0430(12) 0.0331(11) 0.0008(9) 0.0054(9) -0.0060(9) O2 0.0378(8) 0.0520(9) 0.0331(8) -0.0041(7) 0.0041(7) 0.0104(7) O3 0.0658(11) 0.0288(8) 0.0605(10) 0.0061(7) 0.0259(9) 0.0081(7) C18 0.118(3) 0.0366(14) 0.112(3) 0.0201(16) 0.060(2) 0.0214(16) C19 0.0381(12) 0.0395(12) 0.0502(14) -0.0048(10) 0.0066(11) -0.0060(10) C20 0.0553(15) 0.0381(12) 0.0574(15) 0.0108(11) 0.0090(13) 0.0129(11) O4 0.0349(9) 0.0625(11) 0.0613(11) 0.0042(9) -0.0007(8) 0.0043(8) C21 0.0428(14) 0.0598(17) 0.097(2) 0.0045(16) 0.0136(15) 0.0029(13) O5 0.0467(9) 0.0482(9) 0.0349(8) 0.0028(7) 0.0090(7) -0.0043(7) O6 0.0506(9) 0.0466(9) 0.0393(9) 0.0038(7) 0.0053(8) -0.0005(7) C22 0.0397(12) 0.0465(13) 0.0376(12) -0.0036(10) 0.0127(11) -0.0058(10) C23 0.0507(17) 0.132(3) 0.0586(18) 0.0042(18) 0.0111(15) -0.0331(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O2 91.36(7) . . ? O1 Mn1 N2 178.81(7) . . ? O2 Mn1 N2 87.67(7) . . ? O1 Mn1 O5 92.39(6) . . ? O2 Mn1 O5 159.56(6) . . ? N2 Mn1 O5 88.76(6) . . ? O1 Mn1 N1 88.79(6) . . ? O2 Mn1 N1 108.61(7) . . ? N2 Mn1 N1 90.86(6) . . ? O5 Mn1 N1 91.56(6) . . ? O1 Mn1 O6 90.02(6) . . ? O2 Mn1 O6 100.55(6) . . ? N2 Mn1 O6 90.84(6) . . ? O5 Mn1 O6 59.37(6) . . ? N1 Mn1 O6 150.84(6) . . ? O1 Mn1 C22 90.74(7) . . ? O2 Mn1 C22 130.00(7) . . ? N2 Mn1 C22 90.42(7) . . ? O5 Mn1 C22 29.90(6) . . ? N1 Mn1 C22 121.38(7) . . ? O6 Mn1 C22 29.49(6) . . ? C1 O1 Mn1 123.49(12) . . ? O1 C1 C6 123.54(18) . . ? O1 C1 C2 117.95(18) . . ? C6 C1 C2 118.35(18) . . ? O3 C2 C3 125.1(2) . . ? O3 C2 C1 114.59(18) . . ? C3 C2 C1 120.3(2) . . ? C2 C3 C4 120.9(2) . . ? C2 C3 H3A 119.6 . . ? C4 C3 H3A 119.6 . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H5A 119.6 . . ? C6 C5 H5A 119.6 . . ? C5 C6 C1 119.54(19) . . ? C5 C6 C7 118.09(19) . . ? C1 C6 C7 122.16(18) . . ? N1 C7 C6 125.98(19) . . ? N1 C7 H7A 117.0 . . ? C6 C7 H7A 117.0 . . ? C7 N1 C8 118.12(17) . . ? C7 N1 Mn1 120.31(14) . . ? C8 N1 Mn1 121.47(13) . . ? N1 C8 C9 114.57(16) . . ? N1 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? N1 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C19 C9 C8 110.84(17) . . ? C19 C9 C20 110.98(18) . . ? C8 C9 C20 107.04(17) . . ? C19 C9 C10 110.64(18) . . ? C8 C9 C10 111.26(17) . . ? C20 C9 C10 105.92(17) . . ? N2 C10 C9 113.35(16) . . ? N2 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? N2 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C11 N2 C10 118.96(17) . . ? C11 N2 Mn1 122.67(14) . . ? C10 N2 Mn1 118.37(13) . . ? N2 C11 C12 125.77(19) . . ? N2 C11 H11A 117.1 . . ? C12 C11 H11A 117.1 . . ? C13 C12 C17 120.1(2) . . ? C13 C12 C11 119.0(2) . . ? C17 C12 C11 120.44(19) . . ? C14 C13 C12 120.7(2) . . ? C14 C13 H13A 119.7 . . ? C12 C13 H13A 119.7 . . ? C13 C14 C15 119.5(2) . . ? C13 C14 H14A 120.3 . . ? C15 C14 H14A 120.3 . . ? C16 C15 C14 121.6(2) . . ? C16 C15 H15A 119.2 . . ? C14 C15 H15A 119.2 . . ? O4 C16 C15 118.1(2) . . ? O4 C16 C17 121.1(2) . . ? C15 C16 C17 120.7(2) . . ? O2 C17 C12 122.51(19) . . ? O2 C17 C16 120.02(19) . . ? C12 C17 C16 117.41(19) . . ? C17 O2 Mn1 123.62(13) . . ? C2 O3 C18 117.47(19) . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C9 C19 H19A 109.5 . . ? C9 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C9 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C9 C20 H20A 109.5 . . ? C9 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C9 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C16 O4 C21 116.97(18) . . ? O4 C21 H21A 109.5 . . ? O4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C22 O5 Mn1 94.03(14) . . ? C22 O6 Mn1 86.82(13) . . ? O6 C22 O5 119.7(2) . . ? O6 C22 C23 121.6(2) . . ? O5 C22 C23 118.7(2) . . ? O6 C22 Mn1 63.69(12) . . ? O5 C22 Mn1 56.07(11) . . ? C23 C22 Mn1 174.29(18) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 1.8630(14) . ? Mn1 O2 1.9251(15) . ? Mn1 N2 1.9925(16) . ? Mn1 O5 2.1188(16) . ? Mn1 N1 2.1289(17) . ? Mn1 O6 2.2870(16) . ? Mn1 C22 2.547(2) . ? O1 C1 1.318(2) . ? C1 C6 1.411(3) . ? C1 C2 1.422(3) . ? C2 O3 1.361(3) . ? C2 C3 1.369(3) . ? C3 C4 1.390(3) . ? C3 H3A 0.9300 . ? C4 C5 1.371(3) . ? C4 H4A 0.9300 . ? C5 C6 1.400(3) . ? C5 H5A 0.9300 . ? C6 C7 1.449(3) . ? C7 N1 1.274(3) . ? C7 H7A 0.9300 . ? N1 C8 1.470(2) . ? C8 C9 1.532(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C19 1.527(3) . ? C9 C20 1.537(3) . ? C9 C10 1.538(3) . ? C10 N2 1.473(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N2 C11 1.293(3) . ? C11 C12 1.445(3) . ? C11 H11A 0.9300 . ? C12 C13 1.411(3) . ? C12 C17 1.417(3) . ? C13 C14 1.375(4) . ? C13 H13A 0.9300 . ? C14 C15 1.384(4) . ? C14 H14A 0.9300 . ? C15 C16 1.375(3) . ? C15 H15A 0.9300 . ? C16 O4 1.371(3) . ? C16 C17 1.420(3) . ? C17 O2 1.320(3) . ? O3 C18 1.419(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? O4 C21 1.413(3) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? O5 C22 1.273(3) . ? O6 C22 1.256(3) . ? C22 C23 1.490(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C7 H7A O5 0.93 2.56 3.201(2) 126.4 3_656 yes C10 H10A O5 0.97 2.58 3.138(3) 116.7 . yes C18 H18A O6 0.96 2.56 3.512(3) 171.8 2_655 yes C21 H21B O2 0.96 2.37 2.983(3) 121.7 . yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Mn1 O1 C1 65.41(16) . . . . ? O5 Mn1 O1 C1 -134.69(15) . . . . ? N1 Mn1 O1 C1 -43.17(15) . . . . ? O6 Mn1 O1 C1 165.97(15) . . . . ? C22 Mn1 O1 C1 -164.55(16) . . . . ? Mn1 O1 C1 C6 38.2(3) . . . . ? Mn1 O1 C1 C2 -146.50(15) . . . . ? O1 C1 C2 O3 3.3(3) . . . . ? C6 C1 C2 O3 178.86(18) . . . . ? O1 C1 C2 C3 -176.5(2) . . . . ? C6 C1 C2 C3 -0.9(3) . . . . ? O3 C2 C3 C4 -177.1(2) . . . . ? C1 C2 C3 C4 2.6(4) . . . . ? C2 C3 C4 C5 -1.4(4) . . . . ? C3 C4 C5 C6 -1.5(4) . . . . ? C4 C5 C6 C1 3.2(3) . . . . ? C4 C5 C6 C7 178.0(2) . . . . ? O1 C1 C6 C5 173.39(19) . . . . ? C2 C1 C6 C5 -1.9(3) . . . . ? O1 C1 C6 C7 -1.2(3) . . . . ? C2 C1 C6 C7 -176.55(19) . . . . ? C5 C6 C7 N1 170.1(2) . . . . ? C1 C6 C7 N1 -15.2(3) . . . . ? C6 C7 N1 C8 172.47(19) . . . . ? C6 C7 N1 Mn1 -4.0(3) . . . . ? C7 N1 C8 C9 136.83(19) . . . . ? Mn1 N1 C8 C9 -46.7(2) . . . . ? N1 C8 C9 C19 -61.6(2) . . . . ? N1 C8 C9 C20 177.22(18) . . . . ? N1 C8 C9 C10 61.9(2) . . . . ? C19 C9 C10 N2 51.7(2) . . . . ? C8 C9 C10 N2 -72.0(2) . . . . ? C20 C9 C10 N2 172.00(18) . . . . ? C9 C10 N2 C11 -115.9(2) . . . . ? C9 C10 N2 Mn1 64.7(2) . . . . ? C10 N2 C11 C12 169.89(19) . . . . ? Mn1 N2 C11 C12 -10.8(3) . . . . ? N2 C11 C12 C13 170.7(2) . . . . ? N2 C11 C12 C17 -16.6(3) . . . . ? C17 C12 C13 C14 1.0(3) . . . . ? C11 C12 C13 C14 173.7(2) . . . . ? C12 C13 C14 C15 -2.2(4) . . . . ? C13 C14 C15 C16 0.9(4) . . . . ? C14 C15 C16 O4 -173.8(2) . . . . ? C14 C15 C16 C17 1.6(3) . . . . ? C13 C12 C17 O2 178.6(2) . . . . ? C11 C12 C17 O2 6.0(3) . . . . ? C13 C12 C17 C16 1.4(3) . . . . ? C11 C12 C17 C16 -171.17(19) . . . . ? O4 C16 C17 O2 -4.8(3) . . . . ? C15 C16 C17 O2 -180.0(2) . . . . ? O4 C16 C17 C12 172.5(2) . . . . ? C15 C16 C17 C12 -2.7(3) . . . . ? C12 C17 O2 Mn1 31.7(3) . . . . ? C16 C17 O2 Mn1 -151.18(15) . . . . ? C3 C2 O3 C18 4.2(4) . . . . ? C1 C2 O3 C18 -175.6(3) . . . . ? C15 C16 O4 C21 -119.9(3) . . . . ? C17 C16 O4 C21 64.7(3) . . . . ? Mn1 O6 C22 O5 2.1(2) . . . . ? Mn1 O6 C22 C23 -177.5(2) . . . . ? Mn1 O5 C22 O6 -2.3(2) . . . . ? Mn1 O5 C22 C23 177.3(2) . . . . ?