#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:03:36 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268869 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/03/7060333.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_7060333
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         'C21 H21 Co F7 N2'
_chemical_formula_sum            'C21 H21 Co F7 N2'
_chemical_formula_weight         493.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 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                 100.734(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.119(15)
_cell_length_b                   26.21(4)
_cell_length_c                   9.776(16)
_cell_measurement_reflns_used    5320
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.76
_cell_volume                     2296(6)
_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 0.996
_diffrn_measured_fraction_theta_max 0.987
_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 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2535
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.180
_diffrn_reflns_theta_min         2.629
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs-2008/1 (Bruker, 2008)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         2535
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0329
_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)+(0.0547P)²+0.9345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0856
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2417
_reflns_number_total             2535
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj06137a2.cif
_cod_data_source_block           compound_8
_cod_depositor_comments
'Adding full bibliography for 7060330--7060340.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7060333
_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+1/2'
'x+1/2, y+1/2, 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 0.47678(4) 0.17175(2) 0.10424(6) 0.02607(12) Uani 1 1 d . . . . .
C1 C 0.6316(4) 0.11720(12) 0.1343(3) 0.0261(6) Uani 1 1 d . . . . .
N1 N 0.6403(3) 0.07426(11) 0.2208(3) 0.0289(6) Uani 1 1 d . . . . .
N2 N 0.7562(3) 0.11372(11) 0.0725(3) 0.0300(6) Uani 1 1 d . . . . .
C2 C 0.7697(4) 0.04450(14) 0.2126(4) 0.0350(8) Uani 1 1 d . . . . .
H2A H 0.799732 0.013775 0.261454 0.042 Uiso 1 1 calc R U . . .
C3 C 0.8425(4) 0.06929(14) 0.1195(4) 0.0344(8) Uani 1 1 d . . . . .
H3A H 0.932536 0.058840 0.092116 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5317(4) 0.06322(14) 0.3181(4) 0.0329(7) Uani 1 1 d . . . . .
H4A H 0.445947 0.087422 0.294885 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4689(6) 0.00747(17) 0.2967(6) 0.0530(11) Uani 1 1 d . . . . .
H5A H 0.423421 0.002439 0.198655 0.079 Uiso 1 1 calc R U . . .
H5B H 0.393541 0.002147 0.354847 0.079 Uiso 1 1 calc R U . . .
H5C H 0.550525 -0.016994 0.323267 0.079 Uiso 1 1 calc R U . . .
C6 C 0.6111(5) 0.07359(17) 0.4725(4) 0.0453(10) Uani 1 1 d . . . . .
H6A H 0.658293 0.107319 0.478621 0.068 Uiso 1 1 calc R U . . .
H6B H 0.687357 0.047442 0.501639 0.068 Uiso 1 1 calc R U . . .
H6C H 0.537213 0.072481 0.533483 0.068 Uiso 1 1 calc R U . . .
C7 C 0.7978(4) 0.15321(15) -0.0276(4) 0.0358(8) Uani 1 1 d . . . . .
H7A H 0.720940 0.180853 -0.037914 0.043 Uiso 1 1 calc R U . . .
C8 C 0.7936(6) 0.1290(2) -0.1744(5) 0.0523(11) Uani 1 1 d . . . . .
H8A H 0.691552 0.118125 -0.213275 0.078 Uiso 1 1 calc R U . . .
H8B H 0.860448 0.099447 -0.165794 0.078 Uiso 1 1 calc R U . . .
H8C H 0.826183 0.154342 -0.236208 0.078 Uiso 1 1 calc R U . . .
C9 C 0.9535(5) 0.17791(18) 0.0372(6) 0.0505(11) Uani 1 1 d . . . . .
H9A H 0.947877 0.193061 0.127679 0.076 Uiso 1 1 calc R U . . .
H9B H 0.978080 0.204446 -0.025495 0.076 Uiso 1 1 calc R U . . .
H9C H 1.030978 0.151521 0.049404 0.076 Uiso 1 1 calc R U . . .
C11 C 0.3473(4) 0.21224(16) 0.2342(4) 0.0397(8) Uani 1 1 d . . . . .
H11A H 0.257847 0.198726 0.267860 0.048 Uiso 1 1 calc R U . . .
C12 C 0.5018(4) 0.20722(15) 0.3053(4) 0.0381(8) Uani 1 1 d . . . . .
H12A H 0.536576 0.189973 0.396838 0.046 Uiso 1 1 calc R U . . .
C13 C 0.5973(5) 0.23370(15) 0.2225(5) 0.0416(9) Uani 1 1 d . . . . .
H13A H 0.708209 0.237364 0.247135 0.050 Uiso 1 1 calc R U . . .
C14 C 0.5021(6) 0.25444(14) 0.1010(6) 0.0470(11) Uani 1 1 d . . . . .
H14A H 0.535363 0.274793 0.025825 0.056 Uiso 1 1 calc R U . . .
C15 C 0.3459(5) 0.23974(15) 0.1063(4) 0.0420(9) Uani 1 1 d . . . . .
H15A H 0.255281 0.249138 0.036506 0.050 Uiso 1 1 calc R U . . .
C21 C 0.3684(4) 0.14378(12) -0.0762(4) 0.0274(6) Uani 1 1 d . . . . .
C22 C 0.2688(4) 0.10164(13) -0.0861(4) 0.0297(7) Uani 1 1 d . . . . .
C23 C 0.1826(4) 0.08233(13) -0.2128(4) 0.0332(7) Uani 1 1 d . . . . .
C24 C 0.1938(4) 0.10429(14) -0.3429(4) 0.0336(7) Uani 1 1 d . . . . .
C25 C 0.2947(4) 0.14690(15) -0.3374(4) 0.0340(7) Uani 1 1 d . . . . .
C26 C 0.3778(4) 0.16515(13) -0.2090(4) 0.0319(7) Uani 1 1 d . . . . .
C27 C 0.1025(5) 0.08598(17) -0.4846(4) 0.0434(9) Uani 1 1 d . . . . .
F1 F 0.2483(3) 0.07639(9) 0.0350(3) 0.0437(6) Uani 1 1 d . . . . .
F2 F 0.0883(3) 0.04070(9) -0.2063(3) 0.0476(6) Uani 1 1 d . . . . .
F3 F 0.3099(3) 0.17120(11) -0.4599(3) 0.0525(7) Uani 1 1 d . . . . .
F4 F 0.4705(3) 0.20718(9) -0.2178(3) 0.0437(5) Uani 1 1 d . . . . .
F5 F 0.1885(4) 0.0775(2) -0.5793(4) 0.1119(18) Uani 1 1 d . . . . .
F6 F -0.0027(4) 0.12120(14) -0.5415(4) 0.0917(13) Uani 1 1 d . . . . .
F7 F 0.0226(5) 0.04211(13) -0.4764(4) 0.0869(12) 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 95.03(15) . . ?
C1 Co C15 166.94(15) . . ?
C21 Co C15 97.40(16) . . ?
C1 Co C12 102.94(16) . . ?
C21 Co C12 156.85(15) . . ?
C15 Co C12 66.20(16) . . ?
C1 Co C11 135.53(17) . . ?
C21 Co C11 117.68(17) . . ?
C15 Co C11 39.02(18) . . ?
C12 Co C11 39.46(16) . . ?
C1 Co C13 100.58(18) . . ?
C21 Co C13 149.86(17) . . ?
C15 Co C13 66.48(19) . . ?
C12 Co C13 39.77(16) . . ?
C11 Co C13 66.30(18) . . ?
C1 Co C14 129.90(18) . . ?
C21 Co C14 112.88(18) . . ?
C15 Co C14 40.1(2) . . ?
C12 Co C14 65.77(19) . . ?
C11 Co C14 65.94(18) . . ?
C13 Co C14 38.69(19) . . ?
N2 C1 N1 104.6(3) . . ?
N2 C1 Co 126.8(2) . . ?
N1 C1 Co 128.6(3) . . ?
C1 N1 C2 111.1(3) . . ?
C1 N1 C4 124.0(3) . . ?
C2 N1 C4 124.8(3) . . ?
C1 N2 C3 111.1(3) . . ?
C1 N2 C7 124.0(3) . . ?
C3 N2 C7 124.9(3) . . ?
C3 C2 N1 106.4(3) . . ?
C2 C3 N2 106.9(3) . . ?
N1 C4 C5 110.9(3) . . ?
N1 C4 C6 109.3(3) . . ?
C5 C4 C6 112.4(3) . . ?
N2 C7 C8 110.4(3) . . ?
N2 C7 C9 109.5(3) . . ?
C8 C7 C9 113.6(4) . . ?
C15 C11 C12 108.1(4) . . ?
C15 C11 Co 69.8(2) . . ?
C12 C11 Co 69.6(2) . . ?
C11 C12 C13 108.3(4) . . ?
C11 C12 Co 70.9(2) . . ?
C13 C12 Co 70.9(2) . . ?
C14 C13 C12 107.7(4) . . ?
C14 C13 Co 71.1(2) . . ?
C12 C13 Co 69.3(2) . . ?
C13 C14 C15 107.9(4) . . ?
C13 C14 Co 70.3(2) . . ?
C15 C14 Co 68.7(2) . . ?
C11 C15 C14 107.9(4) . . ?
C11 C15 Co 71.2(2) . . ?
C14 C15 Co 71.1(2) . . ?
C22 C21 C26 112.8(3) . . ?
C22 C21 Co 123.4(3) . . ?
C26 C21 Co 123.7(3) . . ?
F1 C22 C21 119.6(3) . . ?
F1 C22 C23 115.3(3) . . ?
C21 C22 C23 125.1(3) . . ?
F2 C23 C24 120.4(3) . . ?
F2 C23 C22 118.7(3) . . ?
C24 C23 C22 120.9(3) . . ?
C23 C24 C25 115.7(3) . . ?
C23 C24 C27 124.0(4) . . ?
C25 C24 C27 120.3(4) . . ?
F3 C25 C26 119.0(3) . . ?
F3 C25 C24 119.3(3) . . ?
C26 C25 C24 121.6(3) . . ?
F4 C26 C25 116.0(3) . . ?
F4 C26 C21 120.1(3) . . ?
C25 C26 C21 123.8(3) . . ?
F5 C27 F7 106.7(4) . . ?
F5 C27 F6 106.7(4) . . ?
F7 C27 F6 104.4(4) . . ?
F5 C27 C24 112.5(4) . . ?
F7 C27 C24 114.1(4) . . ?
F6 C27 C24 111.8(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 1.992(4) . ?
Co C21 1.994(4) . ?
Co C15 2.147(5) . ?
Co C12 2.148(5) . ?
Co C11 2.166(4) . ?
Co C13 2.169(4) . ?
Co C14 2.180(5) . ?
C1 N2 1.386(5) . ?
C1 N1 1.401(5) . ?
N1 C2 1.429(5) . ?
N1 C4 1.523(5) . ?
N2 C3 1.432(5) . ?
N2 C7 1.520(5) . ?
C2 C3 1.385(6) . ?
C4 C5 1.569(6) . ?
C4 C6 1.571(6) . ?
C7 C8 1.563(6) . ?
C7 C9 1.581(6) . ?
C11 C15 1.441(7) . ?
C11 C12 1.456(6) . ?
C12 C13 1.469(6) . ?
C13 C14 1.441(7) . ?
C14 C15 1.485(7) . ?
C21 C22 1.422(5) . ?
C21 C26 1.431(5) . ?
C22 F1 1.399(5) . ?
C22 C23 1.430(5) . ?
C23 F2 1.398(5) . ?
C23 C24 1.417(6) . ?
C24 C25 1.441(6) . ?
C24 C27 1.553(5) . ?
C25 F3 1.386(5) . ?
C25 C26 1.423(5) . ?
C26 F4 1.401(4) . ?
C27 F5 1.339(6) . ?
C27 F7 1.371(6) . ?
C27 F6 1.372(6) . ?
