#------------------------------------------------------------------------------ #$Date: 2020-05-01 04:34:16 +0300 (Fri, 01 May 2020) $ #$Revision: 251350 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240437.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_7240437 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(3-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 ; 2019-12-24 deposited with the CCDC. 2020-04-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 109.5340(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.4258(5) _cell_length_b 9.5785(5) _cell_length_c 13.8330(7) _cell_measurement_reflns_used 2859 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.975 _cell_measurement_theta_min 2.302 _cell_volume 1177.03(11) _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 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.0654 _diffrn_reflns_av_unetI/netI 0.0470 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 15154 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.997 _diffrn_reflns_theta_min 2.303 _exptl_absorpt_coefficient_mu 1.271 _exptl_absorpt_correction_T_max 0.7459 _exptl_absorpt_correction_T_min 0.6196 _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 1.575 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.510 _exptl_crystal_size_mid 0.420 _exptl_crystal_size_min 0.360 _refine_diff_density_max 0.296 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 3115 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_gt 0.0395 _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^)+(0.0304P)^2^+0.2701P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0798 _refine_ls_wR_factor_ref 0.0895 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2287 _reflns_number_total 3115 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02333g2.cif _cod_data_source_block Ant20 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_crystal_density_meas' value 'none' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240437 _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 0.563 _shelx_estimated_absorpt_t_max 0.657 _shelx_res_file ; Ant20.res created by SHELXL-2014/7 TITL Ant20_0m_a.res in P2(1)/n REM Old TITL Ant20_0m in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.102, Rweak 0.005, Alpha 0.044, Orientation as input REM Formula found by SHELXT: C13 N2 O2 Fe CELL 0.71073 9.4258 9.5785 13.8330 90.000 109.534 90.000 ZERR 4.000 0.0005 0.0005 0.0007 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 L.S. 10 omit -2 58 acta BOND $H LIST 6 FMAP 2 PLAN 20 WGHT 0.030400 0.270100 FVAR 0.54988 FE 5 0.229950 0.608334 0.348681 11.00000 0.03571 0.03540 = 0.03231 -0.00012 0.01635 -0.00208 O1 4 0.055443 0.685835 0.140148 11.00000 0.06709 0.05946 = 0.04267 0.00554 0.00319 0.00183 O2 4 0.378515 0.876527 0.404837 11.00000 0.07131 0.05122 = 0.06014 -0.00313 0.01934 -0.02298 N 3 0.686316 0.572339 0.073850 11.00000 0.07865 0.05852 = 0.07876 0.01469 0.05535 0.01246 C1 1 0.123389 0.656930 0.222310 11.00000 0.04169 0.03612 = 0.04363 -0.00243 0.01647 -0.00273 C2 1 0.318021 0.772841 0.381929 11.00000 0.04275 0.04797 = 0.03548 0.00150 0.01613 -0.00200 C3 1 0.277931 0.439533 0.451829 11.00000 0.06313 0.05677 = 0.06538 0.02691 0.03534 0.01036 AFIX 43 H3 2 0.364409 0.384892 0.469452 11.00000 -1.20000 AFIX 0 C4 1 0.144918 0.414562 0.370578 11.00000 0.08678 0.03959 = 0.06260 -0.00663 0.04868 -0.01910 AFIX 43 H4 2 0.127504 0.341449 0.323810 11.00000 -1.20000 AFIX 0 C5 1 0.041954 0.520237 0.372345 11.00000 0.04299 0.07085 = 0.05208 0.00204 0.02340 -0.01750 AFIX 43 H5 2 -0.056366 0.528151 0.327508 11.00000 -1.20000 AFIX 0 C6 1 0.112125 0.610191 0.452177 11.00000 0.06888 0.05007 = 0.05620 0.00043 0.04404 0.00050 AFIX 43 H6 2 0.069941 0.689747 0.469978 11.00000 -1.20000 AFIX 0 C7 1 0.258662 0.559884 0.501634 11.00000 0.06687 0.07206 = 0.03258 0.00620 0.01922 -0.01616 AFIX 43 H7 2 0.330386 0.600428 0.558103 11.00000 -1.20000 AFIX 0 C8 1 0.385246 0.554208 0.295255 11.00000 0.03648 0.04127 = 0.03394 0.00397 0.01248 -0.00165 C9 1 0.474746 0.525345 0.253823 11.00000 0.04131 0.04185 = 0.03665 -0.00001 0.01543 -0.00090 C10 1 0.576299 0.494195 0.199001 11.00000 0.03369 0.04185 = 0.03723 -0.00414 0.01333 -0.00335 C11 1 0.655500 0.369820 0.208610 11.00000 0.04670 0.04167 = 0.05282 0.00297 0.02115 0.00052 AFIX 43 H11 2 0.647632 0.301640 0.254416 11.00000 -1.20000 AFIX 0 C12 1 0.746067 0.348357 0.149482 11.00000 0.04898 0.04551 = 0.06610 -0.00523 0.02559 0.01001 AFIX 43 H12 2 0.798677 0.265058 0.154286 11.00000 -1.20000 AFIX 0 C13 1 0.757485 0.451043 0.083773 11.00000 0.05870 0.06142 = 0.06391 0.00040 0.04052 0.00518 AFIX 43 H13 2 0.818273 0.434948 0.044033 11.00000 -1.20000 AFIX 0 C14 1 0.598544 0.590852 0.130274 11.00000 0.06314 0.04428 = 0.06617 0.00942 0.03938 0.01108 AFIX 43 H14 2 0.547607 0.675403 0.123384 11.00000 -1.20000 AFIX 0 HKLF 4 REM Ant20_0m_a.res in P2(1)/n REM R1 = 0.0395 for 2287 Fo > 4sig(Fo) and 0.0612 for all 3115 data REM 163 parameters refined using 0 restraints END WGHT 0.0273 0.3329 REM Highest difference peak 0.296, deepest hole -0.350, 1-sigma level 0.060 Q1 1 0.6133 0.4389 0.1975 11.00000 0.05 0.30 Q2 1 0.2538 0.6569 0.2836 11.00000 0.05 0.28 Q3 1 0.0731 0.4383 0.3879 11.00000 0.05 0.28 Q4 1 0.3110 0.7034 0.4014 11.00000 0.05 0.27 Q5 1 0.3703 0.6043 0.3933 11.00000 0.05 0.27 Q6 1 0.5629 0.5182 0.1562 11.00000 0.05 0.25 Q7 1 0.1421 0.6982 0.2947 11.00000 0.05 0.25 Q8 1 0.2082 0.3996 0.4266 11.00000 0.05 0.25 Q9 1 0.8013 0.4232 0.1530 11.00000 0.05 0.23 Q10 1 0.2204 0.4854 0.4788 11.00000 0.05 0.23 Q11 1 0.5410 0.5172 0.2256 11.00000 0.05 0.22 Q12 1 0.3019 0.8956 0.3864 11.00000 0.05 0.22 Q13 1 0.2931 0.9392 0.3112 11.00000 0.05 0.22 Q14 1 0.5127 0.4774 0.1982 11.00000 0.05 0.21 Q15 1 0.7148 0.3798 0.1871 11.00000 0.05 0.21 Q16 1 0.2803 0.5499 0.3242 11.00000 0.05 0.21 Q17 1 0.7775 0.3284 0.1518 11.00000 0.05 0.21 Q18 1 0.1289 0.5017 0.3550 11.00000 0.05 0.21 Q19 1 0.1319 0.5132 0.2910 11.00000 0.05 0.21 Q20 1 0.1855 0.5943 0.2813 11.00000 0.05 0.20 ; _shelx_res_checksum 44743 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 0.22995(4) 0.60833(3) 0.34868(2) 0.03322(11) Uani 1 1 d . . . . . O1 O 0.0554(2) 0.6858(2) 0.14015(14) 0.0602(5) Uani 1 1 d . . . . . O2 O 0.3785(2) 0.8765(2) 0.40484(16) 0.0616(6) Uani 1 1 d . . . . . N N 0.6863(3) 0.5723(3) 0.0738(2) 0.0647(7) Uani 1 1 d . . . . . C1 C 0.1234(3) 0.6569(3) 0.2223(2) 0.0399(6) Uani 1 1 d . . . . . C2 C 0.3180(3) 0.7728(3) 0.38193(18) 0.0413(6) Uani 1 1 d . . . . . C3 C 0.2779(4) 0.4395(3) 0.4518(2) 0.0583(8) Uani 1 1 d . . . . . H3 H 0.3644 0.3849 0.4695 0.070 Uiso 1 1 calc R U . . . C4 C 0.1449(4) 0.4146(3) 0.3706(2) 0.0570(8) Uani 1 1 d . . . . . H4 H 0.1275 0.3414 0.3238 0.068 Uiso 1 1 calc R U . . . C5 C 0.0420(3) 0.5202(3) 0.3723(2) 0.0534(7) Uani 1 1 d . . . . . H5 H -0.0564 0.5282 0.3275 0.064 Uiso 1 1 calc R U . . . C6 C 0.1121(3) 0.6102(3) 0.4522(2) 0.0526(7) Uani 1 1 d . . . . . H6 H 0.0699 0.6897 0.4700 0.063 Uiso 1 1 calc R U . . . C7 C 0.2587(3) 0.5599(3) 0.5016(2) 0.0565(8) Uani 1 1 d . . . . . H7 H 0.3304 0.6004 0.5581 0.068 Uiso 1 1 calc R U . . . C8 C 0.3852(3) 0.5542(3) 0.29525(18) 0.0371(5) Uani 1 1 d . . . . . C9 C 0.4747(3) 0.5253(3) 0.25382(18) 0.0393(5) Uani 1 1 d . . . . . C10 C 0.5763(3) 0.4942(3) 0.19900(18) 0.0372(5) Uani 1 1 d . . . . . C11 C 0.6555(3) 0.3698(3) 0.2086(2) 0.0459(6) Uani 1 1 d . . . . . H11 H 0.6476 0.3016 0.2544 0.055 Uiso 1 1 calc R U . . . C12 C 0.7461(3) 0.3484(3) 0.1495(2) 0.0519(7) Uani 1 1 d . . . . . H12 H 0.7987 0.2651 0.1543 0.062 Uiso 1 1 calc R U . . . C13 C 0.7575(3) 0.4510(3) 0.0838(2) 0.0563(7) Uani 1 1 d . . . . . H13 H 0.8183 0.4349 0.0440 0.068 Uiso 1 1 calc R U . . . C14 C 0.5985(3) 0.5909(3) 0.1303(2) 0.0534(7) Uani 1 1 d . . . . . H14 H 0.5476 0.6754 0.1234 0.064 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 0.03571(19) 0.03540(19) 0.03231(18) -0.00012(14) 0.01635(14) -0.00208(15) O1 0.0671(13) 0.0595(13) 0.0427(11) 0.0055(9) 0.0032(10) 0.0018(10) O2 0.0713(14) 0.0512(12) 0.0601(13) -0.0031(10) 0.0193(11) -0.0230(10) N 0.0786(18) 0.0585(15) 0.0788(18) 0.0147(13) 0.0553(16) 0.0125(13) C1 0.0417(13) 0.0361(13) 0.0436(14) -0.0024(11) 0.0165(12) -0.0027(11) C2 0.0427(13) 0.0480(15) 0.0355(13) 0.0015(11) 0.0161(11) -0.0020(12) C3 0.0631(19) 0.0568(17) 0.065(2) 0.0269(15) 0.0353(17) 0.0104(15) C4 0.087(2) 0.0396(15) 0.0626(19) -0.0066(13) 0.0487(18) -0.0191(15) C5 0.0430(15) 0.071(2) 0.0521(16) 0.0020(14) 0.0234(13) -0.0175(14) C6 0.0689(19) 0.0501(16) 0.0562(17) 0.0004(13) 0.0440(15) 0.0005(14) C7 0.067(2) 0.072(2) 0.0326(14) 0.0062(13) 0.0192(14) -0.0162(16) C8 0.0365(13) 0.0413(13) 0.0339(12) 0.0040(10) 0.0125(10) -0.0017(10) C9 0.0413(13) 0.0419(13) 0.0367(13) 0.0000(10) 0.0154(11) -0.0009(11) C10 0.0337(12) 0.0419(13) 0.0372(13) -0.0041(10) 0.0133(10) -0.0033(10) C11 0.0467(15) 0.0417(14) 0.0528(16) 0.0030(12) 0.0211(13) 0.0005(11) C12 0.0490(16) 0.0455(15) 0.0661(18) -0.0052(14) 0.0256(14) 0.0100(12) C13 0.0587(18) 0.0614(18) 0.0639(19) 0.0004(15) 0.0405(16) 0.0052(15) C14 0.0631(18) 0.0443(15) 0.0662(19) 0.0094(13) 0.0394(15) 0.0111(13) 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 94.87(11) . . ? C1 Fe C8 86.82(11) . . ? C2 Fe C8 89.35(11) . . ? C1 Fe C4 105.07(12) . . ? C2 Fe C4 157.78(12) . . ? C8 Fe C4 101.27(11) . . ? C1 Fe C6 114.90(12) . . ? C2 Fe C6 97.20(11) . . ? C8 Fe C6 156.49(11) . . ? C4 Fe C6 65.71(11) . . ? C1 Fe C5 91.73(11) . . ? C2 Fe C5 132.02(12) . . ? C8 Fe C5 138.51(12) . . ? C4 Fe C5 39.49(12) . . ? C6 Fe C5 38.72(11) . . ? C1 Fe C7 154.04(12) . . ? C2 Fe C7 92.51(12) . . ? C8 Fe C7 118.16(11) . . ? C4 Fe C7 65.27(12) . . ? C6 Fe C7 39.32(11) . . ? C5 Fe C7 65.23(11) . . ? C1 Fe C3 142.92(13) . . ? C2 Fe C3 122.19(12) . . ? C8 Fe C3 92.00(11) . . ? C4 Fe C3 38.96(12) . . ? C6 Fe C3 65.40(12) . . ? C5 Fe C3 65.39(12) . . ? C7 Fe C3 38.56(12) . . ? C14 N C13 116.8(2) . . ? O1 C1 Fe 178.6(2) . . ? O2 C2 Fe 177.9(2) . . ? C7 C3 C4 108.1(3) . . ? C7 C3 Fe 70.34(16) . . ? C4 C3 Fe 69.76(16) . . ? C7 C3 H3 125.9 . . ? C4 C3 H3 125.9 . . ? Fe C3 H3 125.5 . . ? C3 C4 C5 107.5(3) . . ? C3 C4 Fe 71.27(16) . . ? C5 C4 Fe 70.31(15) . . ? C3 C4 H4 126.2 . . ? C5 C4 H4 126.2 . . ? Fe C4 H4 123.8 . . ? C6 C5 C4 108.3(3) . . ? C6 C5 Fe 70.63(15) . . ? C4 C5 Fe 70.20(15) . . ? C6 C5 H5 125.9 . . ? C4 C5 H5 125.9 . . ? Fe C5 H5 124.9 . . ? C5 C6 C7 107.8(3) . . ? C5 C6 Fe 70.64(15) . . ? C7 C6 Fe 70.67(15) . . ? C5 C6 H6 126.1 . . ? C7 C6 H6 126.1 . . ? Fe C6 H6 124.2 . . ? C3 C7 C6 108.3(3) . . ? C3 C7 Fe 71.10(16) . . ? C6 C7 Fe 70.01(15) . . ? C3 C7 H7 125.8 . . ? C6 C7 H7 125.9 . . ? Fe C7 H7 124.6 . . ? C9 C8 Fe 174.3(2) . . ? C8 C9 C10 176.8(3) . . ? C11 C10 C14 115.9(2) . . ? C11 C10 C9 124.0(2) . . ? C14 C10 C9 120.1(2) . . ? C12 C11 C10 119.3(2) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C13 C12 C11 119.2(3) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? N C13 C12 123.3(3) . . ? N C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? N C14 C10 125.4(3) . . ? N C14 H14 117.3 . . ? C10 C14 H14 117.3 . . ? 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 1.763(3) . ? Fe C2 1.769(3) . ? Fe C8 1.919(2) . ? Fe C4 2.084(3) . ? Fe C6 2.085(3) . ? Fe C5 2.085(3) . ? Fe C7 2.093(3) . ? Fe C3 2.103(3) . ? O1 C1 1.137(3) . ? O2 C2 1.136(3) . ? N C14 1.326(3) . ? N C13 1.326(4) . ? C3 C7 1.386(4) . ? C3 C4 1.396(4) . ? C3 H3 0.9300 . ? C4 C5 1.408(4) . ? C4 H4 0.9300 . ? C5 C6 1.382(4) . ? C5 H5 0.9300 . ? C6 C7 1.406(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.200(3) . ? C9 C10 1.437(3) . ? C10 C11 1.388(3) . ? C10 C14 1.392(3) . ? C11 C12 1.381(4) . ? C11 H11 0.9300 . ? C12 C13 1.368(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ?