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#$Date: 2020-10-06 14:10:24 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240439.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_7240439
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
 σ-(pyridylethynyl)dicarbonylcyclopentadienyliron complexes
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              17014
_journal_page_last               17025
_journal_paper_doi               10.1039/D0RA02333G
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C15 H8 Fe N2 O2 S'
_chemical_formula_sum            'C15 H8 Fe N2 O2 S'
_chemical_formula_weight         336.14
_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
;
2020-02-07 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.765(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4302(5)
_cell_length_b                   11.8451(10)
_cell_length_c                   17.9823(15)
_cell_measurement_reflns_used    2151
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.44
_cell_measurement_theta_min      2.27
_cell_volume                     1366.69(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker PHOTON II'
_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       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14867
_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         26.963
_diffrn_reflns_theta_min         2.060
_exptl_absorpt_coefficient_mu    1.260
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6461
_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            dark-yellow
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0496
_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/[σ²(Fo²)+(0.0442P)²+0.2917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2227
_reflns_number_total             2964
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra02333g2.cif
_cod_data_source_block           Ant19
_cod_depositor_comments
'Adding full bibliography for 7240436--7240439.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7240439
_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   0.607
_shelx_estimated_absorpt_t_max   0.843
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 0.54770(7) 0.27329(4) 0.51452(2) 0.03574(16) Uani 1 1 d . . . . .
S S -0.29236(17) 0.27855(11) 0.24146(6) 0.0719(3) Uani 1 1 d . . . . .
O1 O 0.2841(4) 0.0741(2) 0.50313(15) 0.0619(7) Uani 1 1 d . . . . .
O2 O 0.2647(4) 0.4089(2) 0.59715(16) 0.0620(7) Uani 1 1 d . . . . .
N1 N -0.0804(5) 0.2843(3) 0.29411(16) 0.0494(7) Uani 1 1 d . . . . .
N2 N -0.2620(5) 0.3824(3) 0.18651(18) 0.0684(10) Uani 1 1 d . . . . .
C1 C 0.3887(5) 0.1522(3) 0.50835(18) 0.0425(8) Uani 1 1 d . . . . .
C2 C 0.3729(5) 0.3546(3) 0.56391(19) 0.0434(8) Uani 1 1 d . . . . .
C3 C 0.4129(5) 0.3252(3) 0.42259(18) 0.0412(8) Uani 1 1 d . . . . .
C4 C 0.8015(5) 0.3781(3) 0.5460(2) 0.0497(9) Uani 1 1 d . . . . .
H4 H 0.7909 0.4548 0.5563 0.060 Uiso 1 1 calc R U . . .
C5 C 0.8330(5) 0.3302(3) 0.4767(2) 0.0505(9) Uani 1 1 d . . . . .
H5 H 0.8495 0.3699 0.4328 0.061 Uiso 1 1 calc R U . . .
C6 C 0.8358(5) 0.2115(3) 0.4841(2) 0.0547(10) Uani 1 1 d . . . . .
H6 H 0.8518 0.1594 0.4463 0.066 Uiso 1 1 calc R U . . .
C7 C 0.8099(5) 0.1866(3) 0.5601(2) 0.0533(9) Uani 1 1 d . . . . .
H7 H 0.8076 0.1149 0.5811 0.064 Uiso 1 1 calc R U . . .
C8 C 0.7885(5) 0.2883(3) 0.5978(2) 0.0536(10) Uani 1 1 d . . . . .
H8 H 0.7690 0.2961 0.6484 0.064 Uiso 1 1 calc R U . . .
C9 C 0.3256(5) 0.3594(3) 0.36550(19) 0.0436(8) Uani 1 1 d . . . . .
C10 C 0.2263(5) 0.4106(3) 0.30016(18) 0.0427(8) Uani 1 1 d . . . . .
C11 C 0.3099(6) 0.5010(3) 0.26395(19) 0.0504(9) Uani 1 1 d . . . . .
H11 H 0.4418 0.5260 0.2808 0.060 Uiso 1 1 calc R U . . .
C12 C 0.2075(7) 0.5580(3) 0.2028(2) 0.0582(10) Uani 1 1 d . . . . .
H12 H 0.2714 0.6193 0.1814 0.070 Uiso 1 1 calc R U . . .
C13 C 0.0161(7) 0.5234(3) 0.1753(2) 0.0606(11) Uani 1 1 d . . . . .
H13 H -0.0527 0.5609 0.1355 0.073 Uiso 1 1 calc R U . . .
C14 C -0.0756(6) 0.4301(3) 0.20796(18) 0.0485(9) Uani 1 1 d . . . . .
C15 C 0.0277(5) 0.3729(3) 0.26991(17) 0.0413(8) Uani 1 1 d . . . . .
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'
S S 0.1246 0.1234 '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 95.16(15) . . ?
C1 Fe C3 88.80(15) . . ?
C2 Fe C3 89.56(14) . . ?
C1 Fe C8 120.95(15) . . ?
C2 Fe C8 93.38(15) . . ?
C3 Fe C8 149.61(15) . . ?
C1 Fe C7 94.26(15) . . ?
C2 Fe C7 126.43(16) . . ?
C3 Fe C7 143.26(16) . . ?
C8 Fe C7 38.93(14) . . ?
C1 Fe C6 102.63(15) . . ?
C2 Fe C6 157.61(15) . . ?
C3 Fe C6 104.15(15) . . ?
C8 Fe C6 65.85(15) . . ?
C7 Fe C6 39.53(15) . . ?
C1 Fe C4 159.56(15) . . ?
C2 Fe C4 92.94(15) . . ?
C3 Fe C4 110.02(15) . . ?
C8 Fe C4 39.65(14) . . ?
C7 Fe C4 65.98(15) . . ?
C6 Fe C4 65.91(15) . . ?
C1 Fe C5 138.92(16) . . ?
C2 Fe C5 125.79(15) . . ?
C3 Fe C5 88.44(14) . . ?
C8 Fe C5 65.48(15) . . ?
C7 Fe C5 65.67(15) . . ?
C6 Fe C5 39.22(14) . . ?
C4 Fe C5 38.76(14) . . ?
N2 S N1 101.44(17) . . ?
C15 N1 S 106.1(2) . . ?
C14 N2 S 106.6(3) . . ?
O1 C1 Fe 178.8(3) . . ?
O2 C2 Fe 177.9(3) . . ?
C9 C3 Fe 178.6(3) . . ?
C5 C4 C8 107.4(3) . . ?
C5 C4 Fe 71.0(2) . . ?
C8 C4 Fe 69.85(19) . . ?
C5 C4 H4 126.3 . . ?
C8 C4 H4 126.3 . . ?
Fe C4 H4 124.5 . . ?
C4 C5 C6 108.7(3) . . ?
C4 C5 Fe 70.2(2) . . ?
C6 C5 Fe 70.0(2) . . ?
C4 C5 H5 125.6 . . ?
C6 C5 H5 125.6 . . ?
Fe C5 H5 125.8 . . ?
C5 C6 C7 107.3(3) . . ?
C5 C6 Fe 70.8(2) . . ?
C7 C6 Fe 70.1(2) . . ?
C5 C6 H6 126.3 . . ?
C7 C6 H6 126.3 . . ?
Fe C6 H6 124.3 . . ?
C8 C7 C6 108.1(3) . . ?
C8 C7 Fe 70.36(19) . . ?
C6 C7 Fe 70.3(2) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
Fe C7 H7 124.9 . . ?
C7 C8 C4 108.4(3) . . ?
C7 C8 Fe 70.71(19) . . ?
C4 C8 Fe 70.50(19) . . ?
C7 C8 H8 125.8 . . ?
C4 C8 H8 125.8 . . ?
Fe C8 H8 124.6 . . ?
C3 C9 C10 174.6(4) . . ?
C11 C10 C15 115.5(3) . . ?
C11 C10 C9 123.2(3) . . ?
C15 C10 C9 121.3(3) . . ?
C10 C11 C12 124.1(4) . . ?
C10 C11 H11 117.9 . . ?
C12 C11 H11 117.9 . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 118.8(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
N2 C14 C13 126.7(3) . . ?
N2 C14 C15 112.3(4) . . ?
C13 C14 C15 120.9(3) . . ?
N1 C15 C10 126.1(3) . . ?
N1 C15 C14 113.4(3) . . ?
C10 C15 C14 120.5(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 1.761(4) . ?
Fe C2 1.763(4) . ?
Fe C3 1.917(3) . ?
Fe C8 2.090(3) . ?
Fe C7 2.094(3) . ?
Fe C6 2.097(4) . ?
Fe C4 2.098(3) . ?
Fe C5 2.109(4) . ?
S N2 1.598(4) . ?
S N1 1.609(3) . ?
O1 C1 1.144(4) . ?
O2 C2 1.145(4) . ?
N1 C15 1.347(4) . ?
N2 C14 1.358(5) . ?
C3 C9 1.208(4) . ?
C4 C5 1.396(5) . ?
C4 C8 1.420(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.418(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.394(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.434(4) . ?
C10 C11 1.380(5) . ?
C10 C15 1.426(5) . ?
C11 C12 1.416(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.430(4) . ?
