#------------------------------------------------------------------------------ #$Date: 2020-05-01 04:34:16 +0300 (Fri, 01 May 2020) $ #$Revision: 251350 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240438.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_7240438 loop_ _publ_author_name 'Verpekin, Victor V.' 'Semeikin, Oleg V.' 'Vasiliev, Alexander D.' 'Kondrasenko, Alexander A.' 'Belousov, Yuri A.' 'Ustynyuk, Nikolai A.' _publ_section_title ; Catalyzed M--C coupling reactions in the synthesis of \s-(pyridylethynyl)dicarbonylcyclopentadienyliron complexes ; _journal_issue 29 _journal_name_full 'RSC Advances' _journal_page_first 17014 _journal_paper_doi 10.1039/D0RA02333G _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C14 H9 Fe N O2' _chemical_formula_sum 'C14 H9 Fe N O2' _chemical_formula_weight 279.07 _chemical_name_systematic dicarbonyl(2-pyridylethynyl)(\h^5^-cyclopentadienyl)iron _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-12-23 deposited with the CCDC. 2020-04-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.8340(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.4756(2) _cell_length_b 9.7388(2) _cell_length_c 13.6391(3) _cell_measurement_reflns_used 5131 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 30.47 _cell_measurement_theta_min 2.27 _cell_volume 1191.24(4) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker PHOTON 2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL (Sheldrick 2015)' _computing_structure_solution 'SHELXT (Sheldrick 2015)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker PHOTON-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_unetI/netI 0.0228 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 16740 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.997 _diffrn_reflns_theta_min 2.309 _exptl_absorpt_coefficient_mu 1.256 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_correction_T_min 0.6669 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10. ; _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.556 _exptl_crystal_description prism _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.560 _exptl_crystal_size_mid 0.410 _exptl_crystal_size_min 0.400 _refine_diff_density_max 0.264 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 3475 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0310 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.2647P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0751 _refine_ls_wR_factor_ref 0.0821 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2754 _reflns_number_total 3475 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02333g2.cif _cod_data_source_block v477_a _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240438 _shelx_shelxl_version_number 2014/7 _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 0.540 _shelx_estimated_absorpt_t_max 0.633 _shelx_res_file ; v477_a.res created by SHELXL-2014/7 TITL v477_a.res in P2(1)/n REM Old TITL v477 in P2/n REM SHELXT solution in P2(1)/n REM R1 0.109, Rweak 0.004, Alpha 0.051, Orientation as input REM Formula found by SHELXT: C13 N2 O2 Fe CELL 0.71073 9.4756 9.7388 13.6391 90.000 108.834 90.000 ZERR 4.000 0.0002 0.0002 0.0003 0.000 0.001 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O FE UNIT 56 36 4 8 4 TEMP 23.000 SIZE 0.40 0.41 0.56 L.S. 20 BOND $H ACTA OMIT -2 60 LIST 6 FMAP 2 PLAN 20 WGHT 0.035900 0.264700 FVAR 0.86818 FE 5 0.226448 0.396083 0.348257 11.00000 0.04026 0.04747 = 0.03581 -0.00148 0.01830 0.00222 N 3 0.644522 0.644599 0.221433 11.00000 0.06455 0.05968 = 0.08840 -0.00574 0.03444 -0.00815 C1 1 0.315353 0.234835 0.380052 11.00000 0.04517 0.05692 = 0.03836 -0.00313 0.01818 0.00261 O1 4 0.374920 0.133001 0.402446 11.00000 0.07340 0.06247 = 0.06255 0.00042 0.01987 0.01942 C2 1 0.122098 0.347993 0.219996 11.00000 0.04842 0.05124 = 0.04662 0.00138 0.01925 0.00270 O2 4 0.057317 0.319369 0.137155 11.00000 0.07437 0.07198 = 0.04541 -0.00439 0.00638 -0.00211 C3 1 0.273420 0.559797 0.454082 11.00000 0.07441 0.06630 = 0.06887 -0.02810 0.03672 -0.00942 AFIX 43 H3 2 0.360492 0.611647 0.472742 11.00000 -1.20000 AFIX 0 C4 1 0.249569 0.441202 0.503153 11.00000 0.07076 0.08072 = 0.03925 -0.00781 0.02211 0.01775 AFIX 43 H4 2 0.318092 0.400166 0.560482 11.00000 -1.20000 AFIX 0 C5 1 0.104840 0.393832 0.451700 11.00000 0.06615 0.06731 = 0.05548 0.00209 0.04052 0.00562 AFIX 43 H5 2 0.060945 0.315719 0.468414 11.00000 -1.20000 AFIX 0 C6 1 0.038519 0.484588 0.371102 11.00000 0.05233 0.08538 = 0.05847 -0.00084 0.02829 0.02133 AFIX 43 H6 2 -0.058088 0.478199 0.325075 11.00000 -1.20000 AFIX 0 C7 1 0.142773 0.587740 0.371198 11.00000 0.09757 0.05314 = 0.06829 0.00789 0.05136 0.02202 AFIX 43 H7 2 0.128012 0.660777 0.325044 11.00000 -1.20000 AFIX 0 C8 1 0.380733 0.452616 0.294482 11.00000 0.04423 0.04793 = 0.04169 -0.00336 0.01742 -0.00081 C9 1 0.472780 0.484260 0.254998 11.00000 0.04521 0.05176 = 0.04571 -0.00088 0.01825 0.00008 C10 1 0.575666 0.521626 0.201902 11.00000 0.03892 0.04841 = 0.04471 0.00464 0.01545 0.00165 C11 1 0.603076 0.430748 0.133902 11.00000 0.09642 0.06492 = 0.09050 -0.02483 0.06613 -0.02500 AFIX 43 H11 2 0.557834 0.344822 0.123661 11.00000 -1.20000 AFIX 0 C12 1 0.697016 0.467217 0.081474 11.00000 0.12338 0.10558 = 0.11885 -0.03534 0.09546 -0.02293 AFIX 43 H12 2 0.715571 0.405683 0.034940 11.00000 -1.20000 AFIX 0 C13 1 0.763681 0.590766 0.095675 11.00000 0.06342 0.10090 = 0.08287 0.01452 0.04576 -0.00320 AFIX 43 H13 2 0.825853 0.616742 0.058295 11.00000 -1.20000 AFIX 0 C14 1 0.737464 0.676110 0.166060 11.00000 0.06071 0.06454 = 0.10479 0.01139 0.02919 -0.01316 AFIX 43 H14 2 0.785247 0.760858 0.177430 11.00000 -1.20000 AFIX 0 HKLF 4 REM v477_a.res in P2(1)/n REM R1 = 0.0310 for 2754 Fo > 4sig(Fo) and 0.0440 for all 3475 data REM 163 parameters refined using 0 restraints END WGHT 0.0354 0.2658 REM Highest difference peak 0.264, deepest hole -0.265, 1-sigma level 0.045 Q1 1 0.6206 0.3986 0.1478 11.00000 0.05 0.26 Q2 1 0.6643 0.4463 0.1282 11.00000 0.05 0.26 Q3 1 0.6376 0.4512 0.1840 11.00000 0.05 0.25 Q4 1 0.5749 0.5014 0.1097 11.00000 0.05 0.23 Q5 1 0.6192 0.7315 0.2536 11.00000 0.05 0.21 Q6 1 0.2594 0.5199 0.5004 11.00000 0.05 0.20 Q7 1 0.7584 0.5158 0.1147 11.00000 0.05 0.19 Q8 1 0.2029 0.5874 0.4296 11.00000 0.05 0.18 Q9 1 0.1251 0.3625 0.2845 11.00000 0.05 0.18 Q10 1 0.5422 0.4151 0.1035 11.00000 0.05 0.18 Q11 1 0.2355 0.2707 0.3446 11.00000 0.05 0.16 Q12 1 0.2388 0.3598 0.2917 11.00000 0.05 0.16 Q13 1 0.7864 0.6614 0.1420 11.00000 0.05 0.16 Q14 1 0.3014 0.3167 0.3562 11.00000 0.05 0.16 Q15 1 0.4597 0.4361 0.2965 11.00000 0.05 0.16 Q16 1 0.8173 0.7694 0.2446 11.00000 0.05 0.16 Q17 1 0.4005 0.4636 0.2356 11.00000 0.05 0.15 Q18 1 0.4154 0.4952 0.2396 11.00000 0.05 0.15 Q19 1 0.3942 0.1887 0.4310 11.00000 0.05 0.15 Q20 1 0.7488 0.8133 0.2068 11.00000 0.05 0.15 ; _shelx_res_checksum 67727 loop_ _space_group_symop_operation_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' 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 Fe Fe 0.22645(3) 0.39608(2) 0.34826(2) 0.03974(9) Uani 1 1 d . . . . . N N 0.6445(2) 0.64460(19) 0.22143(17) 0.0685(5) Uani 1 1 d . . . . . C1 C 0.31535(19) 0.2348(2) 0.38005(13) 0.0457(4) Uani 1 1 d . . . . . O1 O 0.37492(18) 0.13300(16) 0.40245(12) 0.0666(4) Uani 1 1 d . . . . . C2 C 0.1221(2) 0.34799(19) 0.22000(14) 0.0478(4) Uani 1 1 d . . . . . O2 O 0.05732(17) 0.31937(17) 0.13716(11) 0.0670(4) Uani 1 1 d . . . . . C3 C 0.2734(3) 0.5598(2) 0.45408(18) 0.0666(6) Uani 1 1 d . . . . . H3 H 0.3605 0.6116 0.4727 0.080 Uiso 1 1 calc R U . . . C4 C 0.2496(2) 0.4412(3) 0.50315(15) 0.0625(5) Uani 1 1 d . . . . . H4 H 0.3181 0.4002 0.5605 0.075 Uiso 1 1 calc R U . . . C5 C 0.1048(2) 0.3938(2) 0.45170(16) 0.0580(5) Uani 1 1 d . . . . . H5 H 0.0609 0.3157 0.4684 0.070 Uiso 1 1 calc R U . . . C6 C 0.0385(2) 0.4846(2) 0.37110(16) 0.0629(5) Uani 1 1 d . . . . . H6 H -0.0581 0.4782 0.3251 0.075 Uiso 1 1 calc R U . . . C7 C 0.1428(3) 0.5877(2) 0.37120(19) 0.0671(6) Uani 1 1 d . . . . . H7 H 0.1280 0.6608 0.3250 0.081 Uiso 1 1 calc R U . . . C8 C 0.38073(19) 0.45262(19) 0.29448(13) 0.0438(4) Uani 1 1 d . . . . . C9 C 0.4728(2) 0.48426(19) 0.25500(14) 0.0467(4) Uani 1 1 d . . . . . C10 C 0.57567(18) 0.52163(18) 0.20190(13) 0.0435(4) Uani 1 1 d . . . . . C11 C 0.6031(3) 0.4307(3) 0.1339(2) 0.0753(7) Uani 1 1 d . . . . . H11 H 0.5578 0.3448 0.1237 0.090 Uiso 1 1 calc R U . . . C12 C 0.6970(4) 0.4672(3) 0.0815(3) 0.1024(11) Uani 1 1 d . . . . . H12 H 0.7156 0.4057 0.0349 0.123 Uiso 1 1 calc R U . . . C13 C 0.7637(3) 0.5908(3) 0.0957(2) 0.0771(7) Uani 1 1 d . . . . . H13 H 0.8259 0.6167 0.0583 0.092 Uiso 1 1 calc R U . . . C14 C 0.7375(3) 0.6761(3) 0.1661(2) 0.0761(7) Uani 1 1 d . . . . . H14 H 0.7852 0.7609 0.1774 0.091 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 Fe 0.04026(14) 0.04747(15) 0.03581(13) -0.00148(10) 0.01830(9) 0.00222(9) N 0.0646(11) 0.0597(10) 0.0884(14) -0.0057(10) 0.0344(10) -0.0082(8) C1 0.0452(9) 0.0569(10) 0.0384(8) -0.0031(7) 0.0182(7) 0.0026(8) O1 0.0734(10) 0.0625(9) 0.0626(9) 0.0004(7) 0.0199(7) 0.0194(7) C2 0.0484(10) 0.0512(10) 0.0466(9) 0.0014(8) 0.0192(8) 0.0027(8) O2 0.0744(10) 0.0720(10) 0.0454(7) -0.0044(7) 0.0064(7) -0.0021(8) C3 0.0744(14) 0.0663(13) 0.0689(14) -0.0281(11) 0.0367(12) -0.0094(11) C4 0.0708(13) 0.0807(14) 0.0393(9) -0.0078(10) 0.0221(9) 0.0178(11) C5 0.0662(12) 0.0673(12) 0.0555(11) 0.0021(9) 0.0405(10) 0.0056(10) C6 0.0523(11) 0.0854(15) 0.0585(11) -0.0008(11) 0.0283(9) 0.0213(10) C7 0.0976(18) 0.0531(11) 0.0683(13) 0.0079(10) 0.0514(13) 0.0220(11) C8 0.0442(9) 0.0479(9) 0.0417(8) -0.0034(7) 0.0174(7) -0.0008(7) C9 0.0452(9) 0.0518(10) 0.0457(9) -0.0009(8) 0.0182(7) 0.0001(7) C10 0.0389(8) 0.0484(9) 0.0447(8) 0.0046(7) 0.0155(7) 0.0016(7) C11 0.0964(18) 0.0649(13) 0.0905(17) -0.0248(12) 0.0661(15) -0.0250(12) C12 0.123(2) 0.106(2) 0.119(2) -0.0353(19) 0.095(2) -0.0229(19) C13 0.0634(14) 0.1009(19) 0.0829(17) 0.0145(14) 0.0458(13) -0.0032(12) C14 0.0607(13) 0.0645(14) 0.1048(19) 0.0114(14) 0.0292(13) -0.0132(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Fe Fe 0.3463 0.8444 '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 C1 Fe C2 94.43(8) . . ? C1 Fe C8 89.26(8) . . ? C2 Fe C8 87.11(8) . . ? C1 Fe C6 133.70(9) . . ? C2 Fe C6 91.46(9) . . ? C8 Fe C6 136.94(9) . . ? C1 Fe C7 158.39(9) . . ? C2 Fe C7 105.43(9) . . ? C8 Fe C7 100.01(8) . . ? C6 Fe C7 39.38(9) . . ? C1 Fe C5 98.51(8) . . ? C2 Fe C5 114.21(9) . . ? C8 Fe C5 156.42(8) . . ? C6 Fe C5 38.91(8) . . ? C7 Fe C5 65.79(8) . . ? C1 Fe C4 93.00(8) . . ? C2 Fe C4 153.20(9) . . ? C8 Fe C4 118.72(9) . . ? C6 Fe C4 65.21(8) . . ? C7 Fe C4 65.41(9) . . ? C5 Fe C4 39.10(9) . . ? C1 Fe C3 121.82(9) . . ? C2 Fe C3 143.72(10) . . ? C8 Fe C3 91.51(8) . . ? C6 Fe C3 65.55(9) . . ? C7 Fe C3 39.25(10) . . ? C5 Fe C3 65.46(9) . . ? C4 Fe C3 38.65(9) . . ? C10 N C14 116.6(2) . . ? O1 C1 Fe 178.29(17) . . ? O2 C2 Fe 178.38(18) . . ? C4 C3 C7 108.1(2) . . ? C4 C3 Fe 70.65(12) . . ? C7 C3 Fe 70.03(12) . . ? C4 C3 H3 126.0 . . ? C7 C3 H3 126.0 . . ? Fe C3 H3 125.0 . . ? C3 C4 C5 108.5(2) . . ? C3 C4 Fe 70.70(11) . . ? C5 C4 Fe 70.11(11) . . ? C3 C4 H4 125.7 . . ? C5 C4 H4 125.7 . . ? Fe C4 H4 125.0 . . ? C6 C5 C4 107.8(2) . . ? C6 C5 Fe 70.55(10) . . ? C4 C5 Fe 70.79(11) . . ? C6 C5 H5 126.1 . . ? C4 C5 H5 126.1 . . ? Fe C5 H5 124.2 . . ? C5 C6 C7 108.3(2) . . ? C5 C6 Fe 70.54(11) . . ? C7 C6 Fe 70.32(11) . . ? C5 C6 H6 125.8 . . ? C7 C6 H6 125.8 . . ? Fe C6 H6 124.9 . . ? C6 C7 C3 107.3(2) . . ? C6 C7 Fe 70.30(11) . . ? C3 C7 Fe 70.72(12) . . ? C6 C7 H7 126.3 . . ? C3 C7 H7 126.3 . . ? Fe C7 H7 124.3 . . ? C9 C8 Fe 175.94(16) . . ? C8 C9 C10 176.54(19) . . ? N C10 C11 121.57(17) . . ? N C10 C9 119.29(17) . . ? C11 C10 C9 119.14(17) . . ? C12 C11 C10 119.3(2) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C13 C12 C11 121.1(2) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 117.9(2) . . ? C12 C13 H13 121.1 . . ? C14 C13 H13 121.1 . . ? C13 C14 N 123.6(2) . . ? C13 C14 H14 118.2 . . ? N C14 H14 118.2 . . ? 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 Fe C1 1.7686(19) . ? Fe C2 1.7721(19) . ? Fe C8 1.9159(17) . ? Fe C6 2.0903(18) . ? Fe C7 2.091(2) . ? Fe C5 2.0901(18) . ? Fe C4 2.0989(18) . ? Fe C3 2.100(2) . ? N C10 1.349(2) . ? N C14 1.367(3) . ? C1 O1 1.133(2) . ? C2 O2 1.133(2) . ? C3 C4 1.389(3) . ? C3 C7 1.407(3) . ? C3 H3 0.9300 . ? C4 C5 1.402(3) . ? C4 H4 0.9300 . ? C5 C6 1.392(3) . ? C5 H5 0.9300 . ? C6 C7 1.409(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.204(2) . ? C9 C10 1.436(2) . ? C10 C11 1.366(3) . ? C11 C12 1.357(3) . ? C11 H11 0.9300 . ? C12 C13 1.344(4) . ? C12 H12 0.9300 . ? C13 C14 1.352(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ?