#------------------------------------------------------------------------------
#$Date: 2021-09-06 14:03:36 +0200 (lun 06 de sep de 2021) $
#$Revision: 268869 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/03/7060339.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_7060339
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         'C25 H31 Co F5 N2'
_chemical_formula_sum            'C25 H31 Co F5 N2'
_chemical_formula_weight         513.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                88.611(16)
_cell_angle_beta                 80.883(18)
_cell_angle_gamma                81.458(16)
_cell_formula_units_Z            2
_cell_length_a                   10.152(14)
_cell_length_b                   10.299(14)
_cell_length_c                   11.324(15)
_cell_measurement_reflns_used    6316
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.63
_cell_measurement_theta_min      2.70
_cell_volume                     1156(3)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.969
_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     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.969
_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       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5806
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.758
_diffrn_reflns_theta_min         2.649
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs-2008/1 (Bruker, 2008)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             534
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.064
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0448
_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)+(0.0734P)²+1.5590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1490
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4989
_reflns_number_total             5806
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj06137a2.cif
_cod_data_source_block           compound_10
_cod_depositor_comments
'Adding full bibliography for 7060330--7060340.cif.'
_cod_database_code               7060339
_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, -y, -z'
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 0.75235(3) 0.79376(3) 0.74350(3) 0.01910(12) Uani 1 1 d . . . . .
C1 C 0.8736(3) 0.6390(3) 0.7637(2) 0.0225(5) Uani 1 1 d . . . . .
N1 N 1.0071(2) 0.6155(2) 0.7244(2) 0.0276(5) Uani 1 1 d . . . . .
N2 N 0.8499(2) 0.5286(2) 0.8237(2) 0.0256(5) Uani 1 1 d . . . . .
C2 C 1.0621(3) 0.4951(3) 0.7593(3) 0.0384(7) Uani 1 1 d . . . . .
H2A H 1.154357 0.457481 0.741910 0.046 Uiso 1 1 calc R U . . .
C3 C 0.9648(3) 0.4403(3) 0.8211(3) 0.0379(7) Uani 1 1 d . . . . .
H3A H 0.972494 0.355797 0.857028 0.046 Uiso 1 1 calc R U . . .
C4 C 1.0800(3) 0.7009(3) 0.6444(3) 0.0307(6) Uani 1 1 d . . . . .
H4A H 1.018683 0.784981 0.636460 0.037 Uiso 1 1 calc R U . . .
C5 C 1.1997(3) 0.7314(4) 0.6944(4) 0.0466(8) Uani 1 1 d . . . . .
H5A H 1.170353 0.768439 0.774828 0.070 Uiso 1 1 calc R U . . .
H5B H 1.243804 0.795133 0.642594 0.070 Uiso 1 1 calc R U . . .
H5C H 1.263520 0.650702 0.698614 0.070 Uiso 1 1 calc R U . . .
C6 C 1.1191(4) 0.6381(4) 0.5235(3) 0.0423(8) Uani 1 1 d . . . . .
H6A H 1.038149 0.619029 0.494327 0.064 Uiso 1 1 calc R U . . .
H6B H 1.180688 0.556135 0.529302 0.064 Uiso 1 1 calc R U . . .
H6C H 1.164120 0.697928 0.467773 0.064 Uiso 1 1 calc R U . . .
C7 C 0.7176(3) 0.5022(3) 0.8756(2) 0.0268(5) Uani 1 1 d . . . . .
H7A H 0.652132 0.583914 0.869772 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7135(4) 0.4669(3) 1.0054(3) 0.0396(7) Uani 1 1 d . . . . .
H8A H 0.744564 0.536175 1.047024 0.059 Uiso 1 1 calc R U . . .
H8B H 0.772301 0.383612 1.012871 0.059 Uiso 1 1 calc R U . . .
H8C H 0.620789 0.458002 1.041151 0.059 Uiso 1 1 calc R U . . .
C9 C 0.6779(3) 0.3968(3) 0.8065(3) 0.0360(7) Uani 1 1 d . . . . .
H9A H 0.687278 0.420676 0.721586 0.054 Uiso 1 1 calc R U . . .
H9B H 0.583875 0.386622 0.836042 0.054 Uiso 1 1 calc R U . . .
H9C H 0.736342 0.313869 0.816429 0.054 Uiso 1 1 calc R U . . .
C11 C 0.8021(3) 0.9673(3) 0.8019(3) 0.0289(6) Uani 1 1 d . . . . .
C12 C 0.7631(3) 0.8862(3) 0.8990(2) 0.0284(6) Uani 1 1 d . . . . .
C13 C 0.6277(3) 0.8702(3) 0.8973(2) 0.0282(6) Uani 1 1 d . . . . .
C14 C 0.5879(3) 0.9340(3) 0.7968(3) 0.0280(6) Uani 1 1 d . . . . .
C15 C 0.6960(3) 0.9944(3) 0.7378(3) 0.0274(5) Uani 1 1 d . . . . .
C16 C 0.9316(4) 1.0193(4) 0.7772(4) 0.0475(9) Uani 1 1 d . . . . .
H16A H 0.922276 1.104679 0.816459 0.071 Uiso 1 1 calc R U . . .
H16B H 0.956954 1.029798 0.690682 0.071 Uiso 1 1 calc R U . . .
H16C H 1.001673 0.958019 0.807989 0.071 Uiso 1 1 calc R U . . .
C17 C 0.8448(4) 0.8372(4) 0.9918(3) 0.0455(8) Uani 1 1 d . . . . .
H17A H 0.835031 0.904459 1.053601 0.068 Uiso 1 1 calc R U . . .
H17B H 0.939792 0.817302 0.955509 0.068 Uiso 1 1 calc R U . . .
H17C H 0.813956 0.757430 1.027849 0.068 Uiso 1 1 calc R U . . .
C18 C 0.5405(4) 0.8047(3) 0.9892(3) 0.0421(8) Uani 1 1 d . . . . .
H18A H 0.479782 0.871018 1.040172 0.063 Uiso 1 1 calc R U . . .
H18B H 0.596480 0.747798 1.038297 0.063 Uiso 1 1 calc R U . . .
H18C H 0.487124 0.751630 0.950362 0.063 Uiso 1 1 calc R U . . .
C19 C 0.4540(3) 0.9458(3) 0.7623(4) 0.0423(8) Uani 1 1 d . . . . .
H19A H 0.399101 1.026645 0.796047 0.063 Uiso 1 1 calc R U . . .
H19B H 0.410844 0.870042 0.792804 0.063 Uiso 1 1 calc R U . . .
H19C H 0.462280 0.948566 0.674916 0.063 Uiso 1 1 calc R U . . .
C20 C 0.6921(4) 1.0782(3) 0.6307(3) 0.0427(8) Uani 1 1 d . . . . .
H20A H 0.657400 1.169088 0.655037 0.064 Uiso 1 1 calc R U . . .
H20B H 0.632904 1.047251 0.580415 0.064 Uiso 1 1 calc R U . . .
H20C H 0.783261 1.073867 0.585473 0.064 Uiso 1 1 calc R U . . .
C21 C 0.6360(3) 0.7153(3) 0.3692(3) 0.0324(6) Uani 1 1 d . . . . .
C22 C 0.7442(3) 0.7748(3) 0.3763(2) 0.0303(6) Uani 1 1 d . . . . .
C23 C 0.7790(3) 0.7919(3) 0.4853(3) 0.0280(6) Uani 1 1 d . . . . .
C24 C 0.7115(3) 0.7514(3) 0.5886(3) 0.0263(5) Uani 1 1 d . . . . .
C25 C 0.6060(3) 0.6932(3) 0.5770(2) 0.0274(6) Uani 1 1 d . . . . .
C26 C 0.5645(3) 0.6745(3) 0.4704(3) 0.0297(6) Uani 1 1 d . . . . .
F1 F 0.88502(18) 0.85456(19) 0.48405(16) 0.0371(4) Uani 1 1 d . . . . .
F2 F 0.8139(2) 0.8150(2) 0.27690(15) 0.0427(5) Uani 1 1 d . . . . .
F3 F 0.6010(2) 0.6975(2) 0.26318(16) 0.0460(5) Uani 1 1 d . . . . .
F4 F 0.45546(19) 0.62119(18) 0.46435(17) 0.0388(4) Uani 1 1 d . . . . .
F5 F 0.53094(18) 0.64818(17) 0.67443(15) 0.0325(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 C24 97.64(12) . . ?
C1 Co C12 98.10(13) . . ?
C24 Co C12 164.21(12) . . ?
C1 Co C14 154.21(12) . . ?
C24 Co C14 98.95(13) . . ?
C12 Co C14 66.77(13) . . ?
C1 Co C15 154.09(12) . . ?
C24 Co C15 98.14(12) . . ?
C12 Co C15 66.71(13) . . ?
C14 Co C15 39.98(12) . . ?
C1 Co C11 116.14(14) . . ?
C24 Co C11 129.42(12) . . ?
C12 Co C11 39.89(11) . . ?
C14 Co C11 66.25(14) . . ?
C15 Co C11 39.04(13) . . ?
C1 Co C13 116.18(13) . . ?
C24 Co C13 131.18(14) . . ?
C12 Co C13 39.97(13) . . ?
C14 Co C13 39.10(12) . . ?
C15 Co C13 66.28(12) . . ?
C11 Co C13 66.30(12) . . ?
N2 C1 N1 102.8(2) . . ?
N2 C1 Co 129.2(2) . . ?
N1 C1 Co 127.9(2) . . ?
C1 N1 C2 111.5(2) . . ?
C1 N1 C4 124.2(2) . . ?
C2 N1 C4 124.0(3) . . ?
C1 N2 C3 111.8(3) . . ?
C1 N2 C7 124.0(2) . . ?
C3 N2 C7 124.0(3) . . ?
C3 C2 N1 107.4(3) . . ?
C3 C2 H2A 126.3 . . ?
N1 C2 H2A 126.3 . . ?
C2 C3 N2 106.5(3) . . ?
C2 C3 H3A 126.8 . . ?
N2 C3 H3A 126.8 . . ?
N1 C4 C5 110.4(3) . . ?
N1 C4 C6 109.3(3) . . ?
C5 C4 C6 112.1(3) . . ?
N1 C4 H4A 108.3 . . ?
C5 C4 H4A 108.3 . . ?
C6 C4 H4A 108.3 . . ?
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 109.9(2) . . ?
N2 C7 C8 110.6(3) . . ?
C9 C7 C8 111.8(3) . . ?
N2 C7 H7A 108.1 . . ?
C9 C7 H7A 108.1 . . ?
C8 C7 H7A 108.1 . . ?
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 108.1(3) . . ?
C15 C11 C16 126.4(3) . . ?
C12 C11 C16 125.4(3) . . ?
C15 C11 Co 69.87(16) . . ?
C12 C11 Co 68.89(17) . . ?
C16 C11 Co 129.2(2) . . ?
C11 C12 C13 107.5(3) . . ?
C11 C12 C17 126.0(3) . . ?
C13 C12 C17 126.3(3) . . ?
C11 C12 Co 71.22(18) . . ?
C13 C12 Co 71.24(15) . . ?
C17 C12 Co 127.1(2) . . ?
C14 C13 C12 107.9(3) . . ?
C14 C13 C18 125.5(3) . . ?
C12 C13 C18 126.5(3) . . ?
C14 C13 Co 69.69(18) . . ?
C12 C13 Co 68.80(16) . . ?
C18 C13 Co 129.8(2) . . ?
C13 C14 C15 108.2(3) . . ?
C13 C14 C19 126.2(3) . . ?
C15 C14 C19 125.4(3) . . ?
C13 C14 Co 71.21(18) . . ?
C15 C14 Co 70.09(19) . . ?
C19 C14 Co 127.9(2) . . ?
C11 C15 C14 108.1(3) . . ?
C11 C15 C20 126.4(3) . . ?
C14 C15 C20 125.3(3) . . ?
C11 C15 Co 71.09(16) . . ?
C14 C15 Co 69.92(17) . . ?
C20 C15 Co 127.4(2) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F3 C21 C22 119.9(3) . . ?
F3 C21 C26 120.8(3) . . ?
C22 C21 C26 119.3(3) . . ?
F2 C22 C21 119.2(3) . . ?
F2 C22 C23 121.6(3) . . ?
C21 C22 C23 119.2(3) . . ?
F1 C23 C24 121.4(3) . . ?
F1 C23 C22 115.0(3) . . ?
C24 C23 C22 123.5(3) . . ?
C25 C24 C23 115.0(3) . . ?
C25 C24 Co 122.3(2) . . ?
C23 C24 Co 122.3(2) . . ?
C24 C25 F5 120.3(3) . . ?
C24 C25 C26 124.4(3) . . ?
F5 C25 C26 115.3(3) . . ?
F4 C26 C21 119.5(3) . . ?
F4 C26 C25 121.9(3) . . ?
C21 C26 C25 118.5(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
Co C1 1.896(3) . ?
Co C24 1.939(4) . ?
Co C12 2.048(3) . ?
Co C14 2.060(3) . ?
Co C15 2.063(4) . ?
Co C11 2.078(3) . ?
Co C13 2.080(3) . ?
C1 N2 1.344(4) . ?
C1 N1 1.345(4) . ?
N1 C2 1.359(4) . ?
N1 C4 1.444(4) . ?
N2 C3 1.365(4) . ?
N2 C7 1.440(4) . ?
C2 C3 1.308(5) . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?
C4 C5 1.496(5) . ?
C4 C6 1.499(5) . ?
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 1.491(4) . ?
C7 C8 1.501(4) . ?
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 1.384(4) . ?
C11 C12 1.408(4) . ?
C11 C16 1.476(5) . ?
C12 C13 1.411(5) . ?
C12 C17 1.474(5) . ?
C13 C14 1.386(4) . ?
C13 C18 1.475(4) . ?
C14 C15 1.410(4) . ?
C14 C19 1.460(5) . ?
C15 C20 1.474(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 F3 1.328(4) . ?
C21 C22 1.349(5) . ?
C21 C26 1.349(5) . ?
C22 F2 1.323(4) . ?
C22 C23 1.360(4) . ?
C23 F1 1.333(3) . ?
C23 C24 1.349(4) . ?
C24 C25 1.328(4) . ?
C25 F5 1.351(3) . ?
C25 C26 1.367(4) . ?
C26 F4 1.318(4) . ?
