#------------------------------------------------------------------------------ #$Date: 2021-11-04 00:58:41 +0200 (Thu, 04 Nov 2021) $ #$Revision: 270270 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/91/7129190.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_7129190 loop_ _publ_author_name 'Mandal, Swadhin K.' 'Chakraborty, Soumi' 'Das, Arpan' _publ_section_title ; Redox-active Ligand Based Mn(I)-Catalyst for Hydrosilylative Ester Reduction ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D1CC05614J _journal_year 2021 _chemical_formula_moiety 'B F4, C22 H14 Mn N2 O4' _chemical_formula_sum 'C22 H14 B F4 Mn N2 O4' _chemical_formula_weight 512.10 _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 geom _atom_sites_solution_primary iterative _audit_creation_date 2021-07-16 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2021-08-05 deposited with the CCDC. 2021-11-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.311(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.7249(7) _cell_length_b 14.4773(7) _cell_length_c 13.6836(6) _cell_measurement_reflns_used 7163 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 65.9650 _cell_measurement_theta_min 4.1810 _cell_volume 2075.8(2) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'olex2.solve 1.3 (Bourhis et al., 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 7.9580 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -14.00 100.00 1.00 1.00 -- 24.33 57.00-180.00 114 2 \w 55.00 119.00 1.00 1.00 -- 24.33-178.00 150.00 64 3 \w 57.00 119.00 1.00 1.00 -- 24.33 178.00 -60.00 62 4 \w -14.00 100.00 1.00 1.00 -- 24.33 57.00 -60.00 114 5 \w 79.00 149.00 1.00 3.00 -- 66.17 151.00 -85.00 70 6 \w -10.00 103.00 1.00 3.00 -- 66.17 -61.00-120.00 113 7 \w -13.00 114.00 1.00 3.00 -- 66.17 -45.00-150.00 127 8 \w 100.00 152.00 1.00 3.00 -- 66.17 111.00 -30.00 52 9 \w 57.00 150.00 1.00 3.00 -- 66.17 178.00-180.00 93 10 \w 19.00 146.00 1.00 3.00 -- 66.17 45.00 -60.00 127 11 \w 65.00 178.00 1.00 3.00 -- 108.00 77.00 -60.00 113 12 \w 23.00 151.00 1.00 3.00 -- 108.00 -77.00-180.00 128 13 \w 86.00 178.00 1.00 3.00 -- 108.00 138.00 60.00 92 14 \w 71.00 178.00 1.00 3.00 -- 108.00 65.00 -30.00 107 15 \w 21.00 113.00 1.00 3.00 -- 108.00-104.00 90.00 92 16 \w 101.00 178.00 1.00 3.00 -- 108.00 104.00-180.00 77 17 \w 58.00 178.00 1.00 3.00 -- 108.00 43.00 -90.00 120 18 \w 101.00 178.00 1.00 3.00 -- 108.00 104.00 120.00 77 19 \w 71.00 178.00 1.00 3.00 -- 108.00 65.00-120.00 107 20 \w 21.00 113.00 1.00 3.00 -- 108.00-104.00-180.00 92 21 \w 26.00 120.00 1.00 3.00 -- 108.00-122.00 31.00 94 22 \w 23.00 151.00 1.00 3.00 -- 108.00 -77.00 30.00 128 23 \w 86.00 178.00 1.00 3.00 -- 108.00 138.00 90.00 92 24 \w 86.00 178.00 1.00 3.00 -- 108.00 138.00 150.00 92 25 \w 31.00 147.00 1.00 3.00 -- 108.00 -54.00 150.00 116 26 \w -57.00 80.00 1.00 1.00 -- 24.33 -38.00-150.00 137 27 \w -14.00 100.00 1.00 1.00 -- 24.33 57.00 60.00 114 28 \w -52.00 62.00 1.00 1.00 -- 24.33 -57.00 60.00 114 29 \w 19.00 146.00 1.00 3.00 -- 66.17 45.00 90.00 127 30 \w 22.00 49.00 1.00 3.00 -- 66.17 78.00 -0.49 27 31 \w 23.00 151.00 1.00 3.00 -- 66.17 77.00-150.00 128 32 \w 19.00 146.00 1.00 3.00 -- 66.17 45.00-180.00 127 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1376022000 _diffrn_orient_matrix_UB_12 0.0356878000 _diffrn_orient_matrix_UB_13 -0.0100933000 _diffrn_orient_matrix_UB_21 0.0470416000 _diffrn_orient_matrix_UB_22 0.0996420000 _diffrn_orient_matrix_UB_23 -0.0077308000 _diffrn_orient_matrix_UB_31 -0.0226723000 _diffrn_orient_matrix_UB_32 -0.0100083000 _diffrn_orient_matrix_UB_33 -0.1145277000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_unetI/netI 0.0306 _diffrn_reflns_Laue_measured_fraction_full 0.972 _diffrn_reflns_Laue_measured_fraction_max 0.972 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 16033 _diffrn_reflns_point_group_measured_fraction_full 0.972 _diffrn_reflns_point_group_measured_fraction_max 0.972 _diffrn_reflns_theta_full 67.280 _diffrn_reflns_theta_max 67.280 _diffrn_reflns_theta_min 4.219 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 5.816 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.34400 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear dark red' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.639 _exptl_crystal_description plate _exptl_crystal_F_000 1032 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.906 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.067 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 3630 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0402 _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^)+(0.0632P)^2^+1.3787P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1070 _refine_ls_wR_factor_ref 0.1124 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3209 _reflns_number_total 3630 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc05614j2.cif _cod_data_source_block sou_mnagbf4 _cod_database_code 7129190 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C H N O Mn B F' _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_max 0.594 _shelx_estimated_absorpt_t_min 0.389 _reflns_odcompleteness_completeness 97.76 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2.a Ternary CH refined with riding coordinates: N1(H1) 2.b Secondary CH2 refined with riding coordinates: C14(H14A,H14B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18), C19(H19) ; _shelx_res_file ; TITL sou_mnagbf4.res created by SHELXL-2018/3 at 12:27:42 on 16-Jul-2021 CELL 1.54184 10.72493 14.477283 13.683595 90 102.3112 90 ZERR 4 0.000678 0.000738 0.000649 0 0.005 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H B F Mn N O UNIT 88 56 4 16 4 8 16 L.S. 20 PLAN 5 SIZE 0.15 0.2 0.1 CONF MORE -1 BOND $H fmap 2 ACTA REM REM REM WGHT 0.063200 1.378700 FVAR 4.30363 B1 3 0.114096 0.232573 0.279426 11.00000 0.03735 0.02432 = 0.02580 0.00293 0.00166 -0.00407 F1 4 -0.018197 0.229036 0.269764 11.00000 0.03666 0.03934 = 0.02825 -0.00132 0.00118 0.00064 F2 4 0.133984 0.242911 0.182073 11.00000 0.06467 0.03598 = 0.04309 0.00721 0.02564 -0.00171 F3 4 0.168793 0.152916 0.320316 11.00000 0.05351 0.04777 = 0.07359 0.03465 0.00838 0.01270 F4 4 0.160064 0.309690 0.334920 11.00000 0.05606 0.05094 = 0.04626 -0.01209 -0.00345 -0.01412 C1 1 0.590112 0.270668 0.449113 11.00000 0.02949 0.02556 = 0.01421 -0.00278 0.00660 0.00378 MN1 5 0.726266 0.143207 0.607541 11.00000 0.02618 0.02233 = 0.01411 0.00060 0.00341 0.00120 N1 6 0.852521 0.233280 0.559670 11.00000 0.02539 0.02087 = 0.01490 -0.00092 0.00007 0.00296 AFIX 13 H1 2 0.928790 0.236994 0.613681 11.00000 -1.20000 AFIX 0 O1 7 0.601945 0.190684 0.485924 11.00000 0.02742 0.02228 = 0.01863 0.00060 0.00263 0.00140 C2 1 0.474202 0.292640 0.377745 11.00000 0.02885 0.03104 = 0.01986 -0.00161 0.00208 0.00121 AFIX 43 H2 2 0.417457 0.245654 0.352146 11.00000 -1.20000 AFIX 0 N2 6 0.787568 0.057819 0.508882 11.00000 0.02681 0.02092 = 0.01722 -0.00003 0.00190 0.00008 O2 7 0.670711 0.279192 0.753371 11.00000 0.03951 0.03207 = 0.02111 -0.00108 0.00702 0.00416 C3 1 0.447206 0.380264 0.347776 11.00000 0.03027 0.03504 = 0.01888 0.00191 0.00086 0.00835 AFIX 43 H3 2 0.370562 0.392771 0.303352 11.00000 -1.20000 AFIX 0 O3 7 0.522916 0.016353 0.640688 11.00000 0.03727 0.04518 = 0.03194 -0.00029 0.01057 -0.01016 C4 1 0.533598 0.455271 0.382515 11.00000 0.03210 0.02810 = 0.01809 0.00176 0.00615 0.00834 O4 7 0.896533 0.057843 0.782158 11.00000 0.04062 0.03825 = 0.02737 0.01150 -0.00098 0.00219 C5 1 0.504395 0.545241 0.351505 11.00000 0.03866 0.03196 = 0.02258 0.00382 0.00404 0.01235 AFIX 43 H5 2 0.426973 0.557773 0.308096 11.00000 -1.20000 AFIX 0 C6 1 0.589309 0.617423 0.384362 11.00000 0.04890 0.02376 = 0.02741 0.00472 0.00768 0.00960 AFIX 43 H6 2 0.568431 0.677312 0.362198 11.00000 -1.20000 AFIX 0 C7 1 0.703044 0.600478 0.448986 11.00000 0.04385 0.02222 = 0.02612 -0.00044 0.00898 0.00156 AFIX 43 H7 2 0.758527 0.649108 0.471176 11.00000 -1.20000 AFIX 0 C8 1 0.737094 0.509424 0.482440 11.00000 0.03757 0.02289 = 0.01821 -0.00019 0.00794 0.00314 C9 1 0.853866 0.489414 0.547686 11.00000 0.03566 0.02519 = 0.02084 -0.00191 0.00481 -0.00117 AFIX 43 H9 2 0.908630 0.537533 0.573230 11.00000 -1.20000 AFIX 0 C10 1 0.888690 0.400205 0.574458 11.00000 0.03053 0.02614 = 0.01936 -0.00191 0.00256 0.00084 AFIX 43 H10 2 0.967601 0.388241 0.616065 11.00000 -1.20000 AFIX 0 C11 1 0.805750 0.327256 0.539298 11.00000 0.02944 0.02051 = 0.01475 0.00044 0.00526 0.00249 C12 1 0.684744 0.343492 0.479777 11.00000 0.02890 0.02440 = 0.01336 -0.00157 0.00558 0.00340 C13 1 0.651083 0.436112 0.448317 11.00000 0.03367 0.02411 = 0.01528 0.00087 0.00815 0.00530 C14 1 0.894500 0.195775 0.469488 11.00000 0.02935 0.02124 = 0.02186 -0.00015 0.00821 0.00089 AFIX 23 H14A 2 0.854281 0.231106 0.411006 11.00000 -1.20000 H14B 2 0.986142 0.203155 0.478510 11.00000 -1.20000 AFIX 0 C15 1 0.861066 0.095935 0.452056 11.00000 0.02548 0.02075 = 0.01888 0.00086 0.00072 0.00236 C16 1 0.902689 0.046977 0.377994 11.00000 0.03088 0.02486 = 0.02189 -0.00040 0.00758 0.00174 AFIX 43 H16 2 0.954253 0.074946 0.339875 11.00000 -1.20000 AFIX 0 C17 1 0.866005 -0.044248 0.361950 11.00000 0.03346 0.02536 = 0.02456 -0.00493 0.00464 0.00297 AFIX 43 H17 2 0.890886 -0.078292 0.311713 11.00000 -1.20000 AFIX 0 C18 1 0.791718 -0.084227 0.421698 11.00000 0.03205 0.01989 = 0.03100 -0.00173 0.00371 0.00006 AFIX 43 H18 2 0.766904 -0.145726 0.412591 11.00000 -1.20000 AFIX 0 C19 1 0.755246 -0.032349 0.494203 11.00000 0.03003 0.02297 = 0.02487 0.00315 0.00577 0.00055 AFIX 43 H19 2 0.706568 -0.059885 0.534864 11.00000 -1.20000 AFIX 0 C20 1 0.834090 0.091689 0.712959 11.00000 0.03094 0.02335 = 0.02547 0.00056 0.00896 -0.00113 C21 1 0.602522 0.065474 0.629430 11.00000 0.03116 0.03152 = 0.01660 0.00028 0.00342 0.00161 C22 1 0.687917 0.227339 0.694161 11.00000 0.02618 0.02772 = 0.01747 0.00456 0.00195 0.00227 HKLF 4 REM REM wR2 = 0.1124, GooF = S = 1.069, Restrained GooF = 1.069 for all data REM R1 = 0.0402 for 3209 Fo > 4sig(Fo) and 0.0469 for all 3630 data REM 307 parameters refined using 0 restraints END WGHT 0.0632 1.3786 REM Highest difference peak 0.906, deepest hole -0.394, 1-sigma level 0.067 Q1 1 0.2216 0.2563 0.2269 11.00000 0.05 0.91 Q2 1 0.1724 0.2446 0.3867 11.00000 0.05 0.80 Q3 1 0.8128 0.1371 0.6262 11.00000 0.05 0.43 Q4 1 0.0354 0.2547 0.2306 11.00000 0.05 0.41 Q5 1 0.1257 0.1212 0.2631 11.00000 0.05 0.39 ; _shelx_res_checksum 92169 _olex2_date_sample_data_collection 2020-02-07 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.655 _oxdiff_exptl_absorpt_empirical_full_min 0.540 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 B1 B 0.1141(3) 0.2326(2) 0.2794(2) 0.0299(7) Uani 1 1 d . . . . . F1 F -0.01820(16) 0.22904(12) 0.26976(12) 0.0356(4) Uani 1 1 d . . . . . F2 F 0.1340(2) 0.24291(12) 0.18207(14) 0.0458(5) Uani 1 1 d . . . . . F3 F 0.1688(2) 0.15292(14) 0.32032(18) 0.0591(6) Uani 1 1 d . . . . . F4 F 0.1601(2) 0.30969(14) 0.33492(15) 0.0532(5) Uani 1 1 d . . . . . C1 C 0.5901(3) 0.27067(18) 0.44911(18) 0.0228(5) Uani 1 1 d . . . . . Mn1 Mn 0.72627(4) 0.14321(3) 0.60754(3) 0.02100(14) Uani 1 1 d . . . . . N1 N 0.8525(2) 0.23328(14) 0.55967(15) 0.0210(5) Uani 1 1 d . . . . . H1 H 0.928790 0.236994 0.613681 0.025 Uiso 1 1 calc R U . . . O1 O 0.60194(17) 0.19068(12) 0.48592(13) 0.0231(4) Uani 1 1 d . . . . . C2 C 0.4742(3) 0.2926(2) 0.37775(19) 0.0270(6) Uani 1 1 d . . . . . H2 H 0.417457 0.245654 0.352146 0.032 Uiso 1 1 calc R U . . . N2 N 0.7876(2) 0.05782(14) 0.50888(15) 0.0221(5) Uani 1 1 d . . . . . O2 O 0.67071(19) 0.27919(14) 0.75337(14) 0.0308(4) Uani 1 1 d . . . . . C3 C 0.4472(3) 0.3803(2) 0.3478(2) 0.0287(6) Uani 1 1 d . . . . . H3 H 0.370562 0.392771 0.303352 0.034 Uiso 1 1 calc R U . . . O3 O 0.5229(2) 0.01635(15) 0.64069(15) 0.0377(5) Uani 1 1 d . . . . . C4 C 0.5336(3) 0.45527(19) 0.38252(19) 0.0260(6) Uani 1 1 d . . . . . O4 O 0.8965(2) 0.05784(15) 0.78216(15) 0.0366(5) Uani 1 1 d . . . . . C5 C 0.5044(3) 0.5452(2) 0.3515(2) 0.0314(6) Uani 1 1 d . . . . . H5 H 0.426973 0.557773 0.308096 0.038 Uiso 1 1 calc R U . . . C6 C 0.5893(3) 0.6174(2) 0.3844(2) 0.0334(7) Uani 1 1 d . . . . . H6 H 0.568431 0.677312 0.362198 0.040 Uiso 1 1 calc R U . . . C7 C 0.7030(3) 0.60048(19) 0.4490(2) 0.0305(6) Uani 1 1 d . . . . . H7 H 0.758527 0.649108 0.471176 0.037 Uiso 1 1 calc R U . . . C8 C 0.7371(3) 0.50942(18) 0.48244(19) 0.0259(6) Uani 1 1 d . . . . . C9 C 0.8539(3) 0.48941(19) 0.54769(19) 0.0274(6) Uani 1 1 d . . . . . H9 H 0.908630 0.537533 0.573230 0.033 Uiso 1 1 calc R U . . . C10 C 0.8887(3) 0.40020(19) 0.57446(19) 0.0258(6) Uani 1 1 d . . . . . H10 H 0.967601 0.388241 0.616065 0.031 Uiso 1 1 calc R U . . . C11 C 0.8058(2) 0.32726(18) 0.53930(18) 0.0215(5) Uani 1 1 d . . . . . C12 C 0.6847(3) 0.34349(18) 0.47978(18) 0.0221(5) Uani 1 1 d . . . . . C13 C 0.6511(3) 0.43611(18) 0.44832(18) 0.0239(6) Uani 1 1 d . . . . . C14 C 0.8945(3) 0.19577(18) 0.46949(19) 0.0237(6) Uani 1 1 d . . . . . H14A H 0.854281 0.231106 0.411006 0.028 Uiso 1 1 calc R U . . . H14B H 0.986142 0.203155 0.478510 0.028 Uiso 1 1 calc R U . . . C15 C 0.8611(2) 0.09594(18) 0.45206(19) 0.0223(5) Uani 1 1 d . . . . . C16 C 0.9027(3) 0.04698(19) 0.3780(2) 0.0256(6) Uani 1 1 d . . . . . H16 H 0.954253 0.074946 0.339875 0.031 Uiso 1 1 calc R U . . . C17 C 0.8660(3) -0.04425(19) 0.3619(2) 0.0280(6) Uani 1 1 d . . . . . H17 H 0.890886 -0.078292 0.311713 0.034 Uiso 1 1 calc R U . . . C18 C 0.7917(3) -0.08423(19) 0.4217(2) 0.0281(6) Uani 1 1 d . . . . . H18 H 0.766904 -0.145726 0.412591 0.034 Uiso 1 1 calc R U . . . C19 C 0.7552(3) -0.03235(18) 0.4942(2) 0.0260(6) Uani 1 1 d . . . . . H19 H 0.706568 -0.059885 0.534864 0.031 Uiso 1 1 calc R U . . . C20 C 0.8341(3) 0.09169(18) 0.7130(2) 0.0261(6) Uani 1 1 d . . . . . C21 C 0.6025(3) 0.0655(2) 0.62943(19) 0.0267(6) Uani 1 1 d . . . . . C22 C 0.6879(2) 0.22734(19) 0.69416(19) 0.0242(6) 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 B1 0.0373(17) 0.0243(16) 0.0258(16) 0.0029(13) 0.0017(13) -0.0041(14) F1 0.0367(9) 0.0393(10) 0.0282(9) -0.0013(7) 0.0012(7) 0.0006(8) F2 0.0647(13) 0.0360(10) 0.0431(11) 0.0072(8) 0.0256(9) -0.0017(9) F3 0.0535(13) 0.0478(12) 0.0736(16) 0.0346(11) 0.0084(11) 0.0127(10) F4 0.0561(12) 0.0509(12) 0.0463(11) -0.0121(10) -0.0034(9) -0.0141(10) C1 0.0295(13) 0.0256(14) 0.0142(12) -0.0028(10) 0.0066(10) 0.0038(11) Mn1 0.0262(2) 0.0223(2) 0.0141(2) 0.00060(16) 0.00341(16) 0.00120(17) N1 0.0254(11) 0.0209(11) 0.0149(10) -0.0009(8) 0.0001(8) 0.0030(9) O1 0.0274(9) 0.0223(10) 0.0186(9) 0.0006(7) 0.0026(7) 0.0014(7) C2 0.0288(14) 0.0310(15) 0.0199(13) -0.0016(11) 0.0021(11) 0.0012(12) N2 0.0268(11) 0.0209(11) 0.0172(10) 0.0000(8) 0.0019(8) 0.0001(9) O2 0.0395(11) 0.0321(11) 0.0211(10) -0.0011(9) 0.0070(8) 0.0042(9) C3 0.0303(14) 0.0350(16) 0.0189(13) 0.0019(11) 0.0009(11) 0.0083(12) O3 0.0373(12) 0.0452(13) 0.0319(11) -0.0003(10) 0.0106(9) -0.0102(10) C4 0.0321(14) 0.0281(14) 0.0181(12) 0.0018(11) 0.0062(11) 0.0083(12) O4 0.0406(12) 0.0383(12) 0.0274(11) 0.0115(9) -0.0010(9) 0.0022(9) C5 0.0387(16) 0.0320(16) 0.0226(14) 0.0038(12) 0.0040(12) 0.0124(13) C6 0.0489(18) 0.0238(14) 0.0274(15) 0.0047(12) 0.0077(13) 0.0096(13) C7 0.0439(17) 0.0222(14) 0.0261(14) -0.0004(11) 0.0090(12) 0.0016(12) C8 0.0376(15) 0.0229(14) 0.0182(12) -0.0002(10) 0.0079(11) 0.0031(12) C9 0.0357(15) 0.0252(14) 0.0208(13) -0.0019(11) 0.0048(11) -0.0012(12) C10 0.0305(14) 0.0261(14) 0.0194(13) -0.0019(11) 0.0026(10) 0.0008(12) C11 0.0294(14) 0.0205(13) 0.0147(12) 0.0004(10) 0.0053(10) 0.0025(11) C12 0.0289(14) 0.0244(14) 0.0134(12) -0.0016(10) 0.0056(10) 0.0034(11) C13 0.0337(15) 0.0241(14) 0.0153(12) 0.0009(10) 0.0081(11) 0.0053(11) C14 0.0293(14) 0.0212(13) 0.0219(13) -0.0002(10) 0.0082(11) 0.0009(11) C15 0.0255(13) 0.0208(13) 0.0189(12) 0.0009(10) 0.0007(10) 0.0024(11) C16 0.0309(14) 0.0249(14) 0.0219(13) -0.0004(11) 0.0076(11) 0.0017(11) C17 0.0335(15) 0.0254(14) 0.0246(14) -0.0049(11) 0.0046(11) 0.0030(12) C18 0.0320(14) 0.0199(13) 0.0310(15) -0.0017(11) 0.0037(12) 0.0001(11) C19 0.0300(14) 0.0230(13) 0.0249(13) 0.0031(11) 0.0058(11) 0.0005(11) C20 0.0309(14) 0.0234(14) 0.0255(14) 0.0006(11) 0.0090(12) -0.0011(11) C21 0.0312(14) 0.0315(15) 0.0166(13) 0.0003(11) 0.0034(11) 0.0016(12) C22 0.0262(13) 0.0277(14) 0.0175(13) 0.0046(11) 0.0020(10) 0.0023(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 F1 B1 F2 105.7(2) . . ? F3 B1 F1 110.4(3) . . ? F3 B1 F2 110.0(3) . . ? F3 B1 F4 112.8(3) . . ? F4 B1 F1 108.5(3) . . ? F4 B1 F2 109.1(2) . . ? O1 C1 C2 118.2(2) . . ? O1 C1 C12 123.0(2) . . ? C2 C1 C12 118.7(2) . . ? O1 Mn1 N1 83.51(8) . . ? O1 Mn1 N2 84.85(8) . . ? N2 Mn1 N1 81.28(8) . . ? C20 Mn1 N1 99.27(10) . . ? C20 Mn1 O1 175.52(10) . . ? C20 Mn1 N2 92.09(10) . . ? C20 Mn1 C21 88.76(12) . . ? C20 Mn1 C22 87.19(12) . . ? C21 Mn1 N1 171.15(10) . . ? C21 Mn1 O1 88.25(10) . . ? C21 Mn1 N2 94.80(11) . . ? C22 Mn1 N1 92.20(10) . . ? C22 Mn1 O1 96.23(9) . . ? C22 Mn1 N2 173.25(11) . . ? C22 Mn1 C21 91.89(12) . . ? Mn1 N1 H1 106.9 . . ? C11 N1 Mn1 115.12(16) . . ? C11 N1 H1 106.9 . . ? C11 N1 C14 109.37(19) . . ? C14 N1 Mn1 111.14(15) . . ? C14 N1 H1 106.9 . . ? C1 O1 Mn1 129.49(17) . . ? C1 C2 H2 119.6 . . ? C3 C2 C1 120.8(3) . . ? C3 C2 H2 119.6 . . ? C15 N2 Mn1 116.58(17) . . ? C15 N2 C19 118.4(2) . . ? C19 N2 Mn1 125.01(18) . . ? C2 C3 H3 119.0 . . ? C2 C3 C4 121.9(3) . . ? C4 C3 H3 119.0 . . ? C5 C4 C3 121.3(3) . . ? C5 C4 C13 119.5(3) . . ? C13 C4 C3 119.1(2) . . ? C4 C5 H5 119.5 . . ? C4 C5 C6 121.1(3) . . ? C6 C5 H5 119.5 . . ? C5 C6 H6 119.8 . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.8 . . ? C6 C7 H7 119.7 . . ? C6 C7 C8 120.6(3) . . ? C8 C7 H7 119.7 . . ? C7 C8 C13 119.0(3) . . ? C9 C8 C7 122.0(3) . . ? C9 C8 C13 119.0(2) . . ? C8 C9 H9 119.4 . . ? C10 C9 C8 121.3(3) . . ? C10 C9 H9 119.4 . . ? C9 C10 H10 119.9 . . ? C9 C10 C11 120.1(3) . . ? C11 C10 H10 119.9 . . ? C10 C11 N1 118.2(2) . . ? C12 C11 N1 120.5(2) . . ? C12 C11 C10 121.1(2) . . ? C11 C12 C1 123.2(2) . . ? C11 C12 C13 118.5(2) . . ? C13 C12 C1 118.3(2) . . ? C4 C13 C8 119.5(2) . . ? C4 C13 C12 120.7(2) . . ? C8 C13 C12 119.8(2) . . ? N1 C14 H14A 109.2 . . ? N1 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C15 C14 N1 112.1(2) . . ? C15 C14 H14A 109.2 . . ? C15 C14 H14B 109.2 . . ? N2 C15 C14 117.2(2) . . ? N2 C15 C16 122.4(2) . . ? C16 C15 C14 120.5(2) . . ? C15 C16 H16 120.7 . . ? C17 C16 C15 118.7(3) . . ? C17 C16 H16 120.7 . . ? C16 C17 H17 120.5 . . ? C16 C17 C18 119.1(3) . . ? C18 C17 H17 120.5 . . ? C17 C18 H18 120.4 . . ? C19 C18 C17 119.3(3) . . ? C19 C18 H18 120.4 . . ? N2 C19 C18 122.2(3) . . ? N2 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? O4 C20 Mn1 176.0(2) . . ? O3 C21 Mn1 178.2(2) . . ? O2 C22 Mn1 175.6(2) . . ? 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 B1 F1 1.398(4) . ? B1 F2 1.401(4) . ? B1 F3 1.359(4) . ? B1 F4 1.381(4) . ? C1 O1 1.258(3) . ? C1 C2 1.443(4) . ? C1 C12 1.462(4) . ? Mn1 N1 2.084(2) . ? Mn1 O1 2.0183(18) . ? Mn1 N2 2.040(2) . ? Mn1 C20 1.806(3) . ? Mn1 C21 1.813(3) . ? Mn1 C22 1.807(3) . ? N1 H1 0.9800 . ? N1 C11 1.456(3) . ? N1 C14 1.502(3) . ? C2 H2 0.9300 . ? C2 C3 1.346(4) . ? N2 C15 1.339(3) . ? N2 C19 1.355(3) . ? O2 C22 1.148(3) . ? C3 H3 0.9300 . ? C3 C4 1.441(4) . ? O3 C21 1.146(3) . ? C4 C5 1.385(4) . ? C4 C13 1.411(4) . ? O4 C20 1.147(3) . ? C5 H5 0.9300 . ? C5 C6 1.396(4) . ? C6 H6 0.9300 . ? C6 C7 1.368(4) . ? C7 H7 0.9300 . ? C7 C8 1.417(4) . ? C8 C9 1.405(4) . ? C8 C13 1.418(4) . ? C9 H9 0.9300 . ? C9 C10 1.372(4) . ? C10 H10 0.9300 . ? C10 C11 1.398(4) . ? C11 C12 1.397(4) . ? C12 C13 1.431(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C15 1.496(4) . ? C15 C16 1.386(4) . ? C16 H16 0.9300 . ? C16 C17 1.382(4) . ? C17 H17 0.9300 . ? C17 C18 1.384(4) . ? C18 H18 0.9300 . ? C18 C19 1.366(4) . ? C19 H19 0.9300 . ? 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 C1 C2 C3 C4 2.0(4) . . . . ? C1 C12 C13 C4 -5.2(4) . . . . ? C1 C12 C13 C8 175.6(2) . . . . ? Mn1 N1 C11 C10 135.8(2) . . . . ? Mn1 N1 C11 C12 -48.9(3) . . . . ? Mn1 N1 C14 C15 -13.5(3) . . . . ? Mn1 N2 C15 C14 2.3(3) . . . . ? Mn1 N2 C15 C16 -176.1(2) . . . . ? Mn1 N2 C19 C18 175.0(2) . . . . ? N1 C11 C12 C1 10.9(4) . . . . ? N1 C11 C12 C13 -169.9(2) . . . . ? N1 C14 C15 N2 7.8(3) . . . . ? N1 C14 C15 C16 -173.9(2) . . . . ? O1 C1 C2 C3 169.5(2) . . . . ? O1 C1 C12 C11 11.3(4) . . . . ? O1 C1 C12 C13 -167.9(2) . . . . ? C2 C1 O1 Mn1 -164.33(17) . . . . ? C2 C1 C12 C11 -172.5(2) . . . . ? C2 C1 C12 C13 8.4(3) . . . . ? C2 C3 C4 C5 -179.7(3) . . . . ? C2 C3 C4 C13 1.3(4) . . . . ? N2 C15 C16 C17 0.5(4) . . . . ? C3 C4 C5 C6 -179.1(3) . . . . ? C3 C4 C13 C8 179.6(2) . . . . ? C3 C4 C13 C12 0.4(4) . . . . ? C4 C5 C6 C7 -0.7(4) . . . . ? C5 C4 C13 C8 0.6(4) . . . . ? C5 C4 C13 C12 -178.6(2) . . . . ? C5 C6 C7 C8 0.9(4) . . . . ? C6 C7 C8 C9 179.1(3) . . . . ? C6 C7 C8 C13 -0.3(4) . . . . ? C7 C8 C9 C10 -175.9(3) . . . . ? C7 C8 C13 C4 -0.4(4) . . . . ? C7 C8 C13 C12 178.8(2) . . . . ? C8 C9 C10 C11 -2.0(4) . . . . ? C9 C8 C13 C4 -179.8(2) . . . . ? C9 C8 C13 C12 -0.6(4) . . . . ? C9 C10 C11 N1 172.8(2) . . . . ? C9 C10 C11 C12 -2.4(4) . . . . ? C10 C11 C12 C1 -174.0(2) . . . . ? C10 C11 C12 C13 5.2(4) . . . . ? C11 N1 C14 C15 -141.7(2) . . . . ? C11 C12 C13 C4 175.6(2) . . . . ? C11 C12 C13 C8 -3.6(4) . . . . ? C12 C1 O1 Mn1 11.9(4) . . . . ? C12 C1 C2 C3 -6.9(4) . . . . ? C13 C4 C5 C6 -0.1(4) . . . . ? C13 C8 C9 C10 3.5(4) . . . . ? C14 N1 C11 C10 -98.2(3) . . . . ? C14 N1 C11 C12 77.0(3) . . . . ? C14 C15 C16 C17 -177.8(2) . . . . ? C15 N2 C19 C18 -2.1(4) . . . . ? C15 C16 C17 C18 -1.5(4) . . . . ? C16 C17 C18 C19 0.8(4) . . . . ? C17 C18 C19 N2 1.1(4) . . . . ? C19 N2 C15 C14 179.6(2) . . . . ? C19 N2 C15 C16 1.3(4) . . . . ?