#------------------------------------------------------------------------------
#$Date: 2021-09-06 14:03:36 +0200 (Mon 06 de Sep de 2021) $
#$Revision: 268869 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/03/7060334.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_7060334
loop_
_publ_author_name
'Ertler, Daniel'
'Kuntze-Fechner, Maximilian W.'
'Dürr, Simon'
'Lubitz, Katharina'
'Radius, Udo'
_publ_section_title
;
 C--F bond activation of perfluorinated arenes using NHC-stabilized cobalt
 half-sandwich complexes
;
_journal_issue                   33
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14999
_journal_page_last               15016
_journal_paper_doi               10.1039/D0NJ06137A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C20 H21 Co F5 N2'
_chemical_formula_sum            'C20 H21 Co F5 N2'
_chemical_formula_weight         443.32
_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
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2020-12-15 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.2220(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1832(13)
_cell_length_b                   24.615(3)
_cell_length_c                   9.5495(13)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.08
_cell_measurement_theta_min      2.52
_cell_volume                     1936.5(4)
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_collection       'Smart-NT v. 5.63'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3836
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.086
_diffrn_reflns_theta_min         2.517
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs-2008/1 (Bruker, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.052
_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     257
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0281
_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/[σ²(Fo²)+(0.0400P)²+0.7663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3525
_reflns_number_total             3836
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj06137a2.cif
_cod_data_source_block           compound_7
_cod_depositor_comments
'Adding full bibliography for 7060330--7060340.cif.'
_cod_original_cell_volume        1936.5(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7060334
_shelx_shelxl_version_number     2018/1
_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.
;
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
Co Co 0.73393(2) 0.15168(2) 0.47111(2) 0.02317(8) Uani 1 1 d . . . . .
F1 F 0.84365(13) 0.07392(4) 0.76808(12) 0.0401(3) Uani 1 1 d . . . . .
F2 F 1.13578(15) 0.05806(5) 1.00710(12) 0.0490(3) Uani 1 1 d . . . . .
F3 F 1.40178(14) 0.11080(6) 1.01880(14) 0.0601(4) Uani 1 1 d . . . . .
F4 F 1.36739(14) 0.18325(6) 0.78929(15) 0.0607(4) Uani 1 1 d . . . . .
F5 F 1.07529(14) 0.20204(5) 0.55384(13) 0.0461(3) Uani 1 1 d . . . . .
C1 C 0.75979(17) 0.10390(6) 0.32371(17) 0.0217(3) Uani 1 1 d . . . . .
N1 N 0.71899(16) 0.05058(5) 0.30012(16) 0.0256(3) Uani 1 1 d . . . . .
N2 N 0.81235(16) 0.11551(5) 0.21432(15) 0.0241(3) Uani 1 1 d . . . . .
C2 C 0.7445(2) 0.02981(7) 0.1781(2) 0.0341(4) Uani 1 1 d . . . . .
H2A H 0.723937 -0.006350 0.139394 0.041 Uiso 1 1 calc R U . . .
C3 C 0.8036(2) 0.07043(7) 0.1248(2) 0.0324(4) Uani 1 1 d . . . . .
H3A H 0.833649 0.068563 0.041682 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6597(2) 0.01814(7) 0.3942(2) 0.0290(3) Uani 1 1 d . . . . .
H4A H 0.641834 0.043425 0.467133 0.035 Uiso 1 1 calc R U . . .
C5 C 0.7860(3) -0.02335(8) 0.4921(2) 0.0427(4) Uani 1 1 d . . . . .
H5A H 0.888259 -0.004781 0.556803 0.064 Uiso 1 1 calc R U . . .
H5B H 0.803304 -0.049376 0.423241 0.064 Uiso 1 1 calc R U . . .
H5C H 0.747850 -0.042677 0.559357 0.064 Uiso 1 1 calc R U . . .
C6 C 0.4976(2) -0.00768(8) 0.2893(2) 0.0434(5) Uani 1 1 d . . . . .
H6A H 0.420026 0.020706 0.229808 0.065 Uiso 1 1 calc R U . . .
H6B H 0.456227 -0.027468 0.353305 0.065 Uiso 1 1 calc R U . . .
H6C H 0.511821 -0.032946 0.216976 0.065 Uiso 1 1 calc R U . . .
C7 C 0.87705(19) 0.16870(6) 0.19663(19) 0.0265(3) Uani 1 1 d . . . . .
H7A H 0.864821 0.194895 0.270773 0.032 Uiso 1 1 calc R U . . .
C8 C 1.0575(2) 0.16315(8) 0.2400(2) 0.0385(4) Uani 1 1 d . . . . .
H8A H 1.113916 0.147438 0.344726 0.058 Uiso 1 1 calc R U . . .
H8B H 1.102924 0.199059 0.238620 0.058 Uiso 1 1 calc R U . . .
H8C H 1.071473 0.139392 0.164478 0.058 Uiso 1 1 calc R U . . .
C9 C 0.7817(2) 0.19031(8) 0.0319(2) 0.0393(4) Uani 1 1 d . . . . .
H9A H 0.666485 0.192779 0.007773 0.059 Uiso 1 1 calc R U . . .
H9B H 0.794760 0.165654 -0.042363 0.059 Uiso 1 1 calc R U . . .
H9C H 0.822220 0.226436 0.023863 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4820(2) 0.15921(9) 0.3716(3) 0.0477(5) Uani 1 1 d . . . . .
H11A H 0.401741 0.132656 0.298893 0.057 Uiso 1 1 calc R U . . .
C12 C 0.5500(2) 0.20398(8) 0.3274(2) 0.0432(5) Uani 1 1 d . . . . .
H12A H 0.526061 0.214459 0.218153 0.052 Uiso 1 1 calc R U . . .
C13 C 0.6517(3) 0.23193(7) 0.4626(2) 0.0434(5) Uani 1 1 d . . . . .
H13A H 0.714393 0.265703 0.467660 0.052 Uiso 1 1 calc R U . . .
C14 C 0.6515(3) 0.20362(8) 0.5915(2) 0.0436(5) Uani 1 1 d . . . . .
H14A H 0.712860 0.214304 0.703580 0.052 Uiso 1 1 calc R U . . .
C15 C 0.5423(3) 0.15991(9) 0.5343(3) 0.0481(5) Uani 1 1 d . . . . .
H15A H 0.513931 0.133703 0.598476 0.058 Uiso 1 1 calc R U . . .
C21 C 0.9454(2) 0.13740(6) 0.64519(18) 0.0266(3) Uani 1 1 d . . . . .
C22 C 0.9711(2) 0.10218(7) 0.76658(19) 0.0299(4) Uani 1 1 d . . . . .
C23 C 1.1202(2) 0.09318(7) 0.8923(2) 0.0353(4) Uani 1 1 d . . . . .
C24 C 1.2545(2) 0.11967(8) 0.8990(2) 0.0395(4) Uani 1 1 d . . . . .
C25 C 1.2368(2) 0.15562(8) 0.7822(2) 0.0393(4) Uani 1 1 d . . . . .
C26 C 1.0851(2) 0.16412(7) 0.6614(2) 0.0329(4) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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 Co C21 96.60(6) . . ?
C1 Co C14 166.92(7) . . ?
C21 Co C14 96.23(7) . . ?
C1 Co C12 102.79(7) . . ?
C21 Co C12 152.16(8) . . ?
C14 Co C12 66.18(7) . . ?
C1 Co C11 101.03(7) . . ?
C21 Co C11 152.96(8) . . ?
C14 Co C11 66.07(9) . . ?
C12 Co C11 39.83(9) . . ?
C1 Co C13 134.65(7) . . ?
C21 Co C13 114.03(8) . . ?
C14 Co C13 39.60(8) . . ?
C12 Co C13 38.93(8) . . ?
C11 Co C13 65.91(9) . . ?
C1 Co C15 130.96(8) . . ?
C21 Co C15 114.59(8) . . ?
C14 Co C15 39.30(9) . . ?
C12 Co C15 65.99(8) . . ?
C11 Co C15 39.02(9) . . ?
C13 Co C15 65.79(8) . . ?
N1 C1 N2 103.98(12) . . ?
N1 C1 Co 126.70(11) . . ?
N2 C1 Co 129.22(11) . . ?
C1 N1 C2 111.12(13) . . ?
C1 N1 C4 124.91(13) . . ?
C2 N1 C4 123.95(13) . . ?
C1 N2 C3 111.27(13) . . ?
C1 N2 C7 124.80(13) . . ?
C3 N2 C7 123.89(13) . . ?
C3 C2 N1 106.94(14) . . ?
C3 C2 H2A 126.5 . . ?
N1 C2 H2A 126.5 . . ?
C2 C3 N2 106.70(14) . . ?
C2 C3 H3A 126.7 . . ?
N2 C3 H3A 126.7 . . ?
N1 C4 C5 110.61(14) . . ?
N1 C4 C6 110.06(14) . . ?
C5 C4 C6 112.60(16) . . ?
N1 C4 H4A 107.8 . . ?
C5 C4 H4A 107.8 . . ?
C6 C4 H4A 107.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C9 110.58(14) . . ?
N2 C7 C8 109.44(13) . . ?
C9 C7 C8 111.86(14) . . ?
N2 C7 H7A 108.3 . . ?
C9 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C11 C12 108.07(19) . . ?
C15 C11 Co 71.35(12) . . ?
C12 C11 Co 70.05(11) . . ?
C15 C11 H11A 125.9 . . ?
C12 C11 H11A 125.9 . . ?
Co C11 H11A 125.9 . . ?
C13 C12 C11 108.05(18) . . ?
C13 C12 Co 71.27(11) . . ?
C11 C12 Co 70.12(11) . . ?
C13 C12 H12A 126.0 . . ?
C11 C12 H12A 126.0 . . ?
Co C12 H12A 126.0 . . ?
C12 C13 C14 107.72(19) . . ?
C12 C13 Co 69.80(10) . . ?
C14 C13 Co 69.04(10) . . ?
C12 C13 H13A 126.1 . . ?
C14 C13 H13A 126.1 . . ?
Co C13 H13A 126.1 . . ?
C15 C14 C13 108.32(18) . . ?
C15 C14 Co 71.68(11) . . ?
C13 C14 Co 71.36(10) . . ?
C15 C14 H14A 125.8 . . ?
C13 C14 H14A 125.8 . . ?
Co C14 H14A 125.8 . . ?
C11 C15 C14 107.72(18) . . ?
C11 C15 Co 69.63(11) . . ?
C14 C15 Co 69.02(11) . . ?
C11 C15 H15A 126.1 . . ?
C14 C15 H15A 126.1 . . ?
Co C15 H15A 126.1 . . ?
C22 C21 C26 113.39(15) . . ?
C22 C21 Co 124.39(13) . . ?
C26 C21 Co 122.17(13) . . ?
F1 C22 C21 119.90(15) . . ?
F1 C22 C23 115.68(16) . . ?
C21 C22 C23 124.42(17) . . ?
F2 C23 C24 119.67(16) . . ?
F2 C23 C22 121.01(17) . . ?
C24 C23 C22 119.31(17) . . ?
F3 C24 C23 120.44(19) . . ?
F3 C24 C25 120.48(18) . . ?
C23 C24 C25 119.08(16) . . ?
F4 C25 C24 119.83(17) . . ?
F4 C25 C26 120.76(19) . . ?
C24 C25 C26 119.39(17) . . ?
F5 C26 C25 116.22(16) . . ?
F5 C26 C21 119.41(16) . . ?
C25 C26 C21 124.36(18) . . ?
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
Co C1 1.9279(15) . ?
Co C21 1.9505(16) . ?
Co C14 2.0730(17) . ?
Co C12 2.0844(18) . ?
Co C11 2.0853(19) . ?
Co C13 2.1034(18) . ?
Co C15 2.1077(19) . ?
F1 C22 1.367(2) . ?
F2 C23 1.353(2) . ?
F3 C24 1.348(2) . ?
F4 C25 1.354(2) . ?
F5 C26 1.361(2) . ?
C1 N1 1.356(2) . ?
C1 N2 1.3607(19) . ?
N1 C2 1.384(2) . ?
N1 C4 1.474(2) . ?
N2 C3 1.381(2) . ?
N2 C7 1.478(2) . ?
C2 C3 1.341(2) . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?
C4 C5 1.518(2) . ?
C4 C6 1.519(2) . ?
C4 H4A 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C9 1.519(2) . ?
C7 C8 1.526(2) . ?
C7 H7A 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C15 1.400(3) . ?
C11 C12 1.420(3) . ?
C11 H11A 1.0000 . ?
C12 C13 1.396(3) . ?
C12 H12A 1.0000 . ?
C13 C14 1.415(3) . ?
C13 H13A 1.0000 . ?
C14 C15 1.406(3) . ?
C14 H14A 1.0000 . ?
C15 H15A 1.0000 . ?
C21 C22 1.382(2) . ?
C21 C26 1.389(2) . ?
C22 C23 1.383(2) . ?
C23 C24 1.372(3) . ?
C24 C25 1.376(3) . ?
C25 C26 1.377(3) . ?
