#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:03:36 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268869 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/03/7060340.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_7060340
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         'C34 H42 Co2 F6 N4'
_chemical_formula_sum            'C40 H48 Co2 F6 N4'
_chemical_formula_weight         816.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/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                 95.84(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.153(5)
_cell_length_b                   18.523(5)
_cell_length_c                   12.963(3)
_cell_measurement_reflns_used    2192
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.3
_cell_volume                     3858.4(18)
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'STOE IPDS 1'
_diffrn_measurement_method       rotation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21863
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.891
_diffrn_reflns_theta_max         25.891
_diffrn_reflns_theta_min         2.199
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3624
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0359
_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)+(0.0501P)²+4.4546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3009
_reflns_number_total             3624
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj06137a2.cif
_cod_data_source_block           compound_14
_cod_depositor_comments
'Adding full bibliography for 7060330--7060340.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7060340
_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.
;
_shelx_estimated_absorpt_t_min   0.866
_shelx_estimated_absorpt_t_max   0.920
_exptl_absorpt_special_details   none
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'
'-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
Co1 Co 0.12291(2) 0.36440(2) 0.15775(2) 0.02383(12) Uani 1 1 d . . . . .
F1 F 0.08399(10) 0.18679(8) 0.27973(16) 0.0564(5) Uani 1 1 d . . . . .
F3 F 0.14265(8) 0.31114(8) 0.37198(11) 0.0369(3) Uani 1 1 d . . . . .
F4 F 0.07102(8) 0.43887(7) 0.33518(11) 0.0297(3) Uani 1 1 d . . . . .
N1 N 0.28073(11) 0.39847(10) 0.28709(16) 0.0283(4) Uani 1 1 d . . . . .
N2 N 0.21598(12) 0.49456(10) 0.23055(15) 0.0266(4) Uani 1 1 d . . . . .
C1 C 0.21011(13) 0.42089(11) 0.22869(17) 0.0234(5) Uani 1 1 d . . . . .
C2 C 0.32796(15) 0.45688(13) 0.3248(2) 0.0377(6) Uani 1 1 d . . . . .
H2 H 0.379352 0.454885 0.367439 0.045 Uiso 1 1 calc R U . . .
C3 C 0.28777(16) 0.51676(13) 0.2900(2) 0.0365(6) Uani 1 1 d . . . . .
H3 H 0.305096 0.565158 0.303474 0.044 Uiso 1 1 calc R U . . .
C4 C 0.30991(15) 0.32235(12) 0.2986(2) 0.0335(6) Uani 1 1 d . . . . .
H4 H 0.263016 0.289897 0.272101 0.040 Uiso 1 1 calc R U . . .
C5 C 0.38133(18) 0.31130(16) 0.2315(3) 0.0553(9) Uani 1 1 d . . . . .
H5A H 0.361893 0.321679 0.158914 0.083 Uiso 1 1 calc R U . . .
H5B H 0.400702 0.261197 0.237708 0.083 Uiso 1 1 calc R U . . .
H5C H 0.427229 0.343918 0.254784 0.083 Uiso 1 1 calc R U . . .
C6 C 0.33483(18) 0.30400(14) 0.4113(2) 0.0460(7) Uani 1 1 d . . . . .
H6A H 0.350180 0.252874 0.417255 0.069 Uiso 1 1 calc R U . . .
H6B H 0.287984 0.313459 0.451822 0.069 Uiso 1 1 calc R U . . .
H6C H 0.382464 0.333798 0.437735 0.069 Uiso 1 1 calc R U . . .
C7 C 0.15756(16) 0.54432(12) 0.17076(19) 0.0307(5) Uani 1 1 d . . . . .
H7 H 0.111230 0.514937 0.135050 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2025(2) 0.58220(17) 0.0878(3) 0.0546(8) Uani 1 1 d . . . . .
H8A H 0.228880 0.546060 0.046655 0.082 Uiso 1 1 calc R U . . .
H8B H 0.245075 0.614617 0.121106 0.082 Uiso 1 1 calc R U . . .
H8C H 0.162260 0.610216 0.042323 0.082 Uiso 1 1 calc R U . . .
C9 C 0.12006(19) 0.59866(14) 0.2403(2) 0.0455(7) Uani 1 1 d . . . . .
H9A H 0.078665 0.628054 0.198704 0.068 Uiso 1 1 calc R U . . .
H9B H 0.164085 0.629978 0.272946 0.068 Uiso 1 1 calc R U . . .
H9C H 0.093210 0.573047 0.294024 0.068 Uiso 1 1 calc R U . . .
C20 C 0.1851(2) 0.3250(3) 0.0341(3) 0.0716(12) Uani 1 1 d . . . . .
H20 H 0.244636 0.309396 0.038776 0.086 Uiso 1 1 calc R U . . .
C21 C 0.1564(3) 0.3926(2) 0.0110(3) 0.0735(13) Uani 1 1 d . . . . .
H21 H 0.191823 0.434821 -0.003800 0.088 Uiso 1 1 calc R U . . .
C22 C 0.0718(3) 0.3936(2) 0.0074(2) 0.0648(10) Uani 1 1 d . . . . .
H22 H 0.034940 0.436078 -0.010983 0.078 Uiso 1 1 calc R U . . .
C23 C 0.04553(19) 0.3243(2) 0.0323(2) 0.0631(11) Uani 1 1 d . . . . .
H23 H -0.013274 0.307634 0.033159 0.076 Uiso 1 1 calc R U . . .
C24 C 0.1180(3) 0.28104(18) 0.0479(3) 0.0710(11) Uani 1 1 d . . . . .
H24 H 0.119969 0.228063 0.062781 0.085 Uiso 1 1 calc R U . . .
C30 C 0.04058(15) 0.24995(12) 0.2636(2) 0.0335(6) Uani 1 1 d . . . . .
C32 C 0.08902(13) 0.31660(12) 0.28008(18) 0.0259(5) Uani 1 1 d . . . . .
C33 C 0.04575(13) 0.38479(11) 0.26290(18) 0.0223(4) Uani 1 1 d . . . . .
C50 C 0.0539(4) -0.0117(6) 0.4239(6) 0.0468(13) Uani 0.624(9) 1 d . U P A 1
H50 H 0.090718 -0.018960 0.372117 0.056 Uiso 0.624(9) 1 calc R U P A 1
C51 C 0.0118(6) 0.0539(5) 0.4308(6) 0.0481(12) Uani 0.624(9) 1 d . U P A 1
H51 H 0.019761 0.091152 0.382437 0.058 Uiso 0.624(9) 1 calc R U P A 1
C52 C -0.0408(5) 0.0656(4) 0.5058(8) 0.0449(12) Uani 0.624(9) 1 d . U P A 1
H52 H -0.068172 0.110726 0.509402 0.054 Uiso 0.624(9) 1 calc R U P A 1
C50B C 0.0373(8) 0.0314(10) 0.4170(8) 0.0462(14) Uani 0.376(9) 1 d . U P A 2
H50B H 0.063645 0.051491 0.361337 0.055 Uiso 0.376(9) 1 calc R U P A 2
C51B C -0.0206(10) 0.0688(6) 0.4649(14) 0.0459(16) Uani 0.376(9) 1 d . U P A 2
H51B H -0.036449 0.116038 0.442353 0.055 Uiso 0.376(9) 1 calc R U P A 2
C52B C 0.0557(7) -0.0374(9) 0.4541(13) 0.0477(16) Uani 0.376(9) 1 d . U P A 2
H52B H 0.095314 -0.064837 0.421235 0.057 Uiso 0.376(9) 1 calc R U P A 2
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'
Co Co 0.3494 0.9721 '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'
N N 0.0061 0.0033 '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 Co1 C32 96.41(10) . . ?
C1 Co1 C33 92.82(9) . . ?
C32 Co1 C33 43.43(9) . . ?
C1 Co1 C23 157.44(12) . . ?
C32 Co1 C23 106.15(12) . . ?
C33 Co1 C23 103.66(11) . . ?
C1 Co1 C21 93.16(13) . . ?
C32 Co1 C21 166.99(13) . . ?
C33 Co1 C21 144.89(16) . . ?
C23 Co1 C21 64.52(14) . . ?
C1 Co1 C24 134.79(15) . . ?
C32 Co1 C24 102.97(13) . . ?
C33 Co1 C24 128.81(15) . . ?
C23 Co1 C24 39.58(15) . . ?
C21 Co1 C24 64.03(15) . . ?
C1 Co1 C20 99.81(12) . . ?
C32 Co1 C20 131.20(16) . . ?
C33 Co1 C20 167.07(13) . . ?
C23 Co1 C20 65.01(13) . . ?
C21 Co1 C20 37.71(17) . . ?
C24 Co1 C20 38.38(16) . . ?
C1 Co1 C22 120.26(15) . . ?
C32 Co1 C22 139.02(15) . . ?
C33 Co1 C22 111.93(13) . . ?
C23 Co1 C22 39.00(16) . . ?
C21 Co1 C22 37.82(16) . . ?
C24 Co1 C22 64.97(14) . . ?
C20 Co1 C22 63.78(15) . . ?
C1 N1 C2 110.91(18) . . ?
C1 N1 C4 125.47(19) . . ?
C2 N1 C4 123.18(19) . . ?
C1 N2 C3 110.97(19) . . ?
C1 N2 C7 124.93(19) . . ?
C3 N2 C7 123.93(19) . . ?
N1 C1 N2 103.93(18) . . ?
N1 C1 Co1 129.17(16) . . ?
N2 C1 Co1 126.89(16) . . ?
C3 C2 N1 107.3(2) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
C2 C3 N2 106.9(2) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
N1 C4 C6 111.1(2) . . ?
N1 C4 C5 108.7(2) . . ?
C6 C4 C5 112.2(2) . . ?
N1 C4 H4 108.3 . . ?
C6 C4 H4 108.3 . . ?
C5 C4 H4 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 111.9(2) . . ?
N2 C7 C8 109.4(2) . . ?
C9 C7 C8 111.1(2) . . ?
N2 C7 H7 108.1 . . ?
C9 C7 H7 108.1 . . ?
C8 C7 H7 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 . . ?
C21 C20 C24 108.4(3) . . ?
C21 C20 Co1 70.73(18) . . ?
C24 C20 Co1 70.44(19) . . ?
C21 C20 H20 125.8 . . ?
C24 C20 H20 125.8 . . ?
Co1 C20 H20 125.8 . . ?
C20 C21 C22 109.9(3) . . ?
C20 C21 Co1 71.6(2) . . ?
C22 C21 Co1 71.60(19) . . ?
C20 C21 H21 125.0 . . ?
C22 C21 H21 125.0 . . ?
Co1 C21 H21 125.0 . . ?
C21 C22 C23 107.7(3) . . ?
C21 C22 Co1 70.6(2) . . ?
C23 C22 Co1 69.57(18) . . ?
C21 C22 H22 126.1 . . ?
C23 C22 H22 126.1 . . ?
Co1 C22 H22 126.1 . . ?
C22 C23 C24 106.7(3) . . ?
C22 C23 Co1 71.43(18) . . ?
C24 C23 Co1 70.68(17) . . ?
C22 C23 H23 126.6 . . ?
C24 C23 H23 126.6 . . ?
Co1 C23 H23 126.6 . . ?
C20 C24 C23 107.2(3) . . ?
C20 C24 Co1 71.18(18) . . ?
C23 C24 Co1 69.74(17) . . ?
C20 C24 H24 126.4 . . ?
C23 C24 H24 126.4 . . ?
Co1 C24 H24 126.4 . . ?
C30 C30 F1 121.27(13) 2 . ?
C30 C30 C32 122.61(12) 2 . ?
F1 C30 C32 116.1(2) . . ?
F3 C32 C33 116.07(19) . . ?
F3 C32 C30 109.70(19) . . ?
C33 C32 C30 118.01(19) . . ?
F3 C32 Co1 121.65(15) . . ?
C33 C32 Co1 69.46(12) . . ?
C30 C32 Co1 117.11(17) . . ?
F4 C33 C32 114.60(19) . . ?
F4 C33 C33 111.49(16) . 2 ?
C32 C33 C33 119.27(12) . 2 ?
F4 C33 Co1 115.85(13) . . ?
C32 C33 Co1 67.12(12) . . ?
C33 C33 Co1 122.0(2) 2 . ?
C52 C50 C51 118.4(6) 5_556 . ?
C52 C50 H50 120.8 5_556 . ?
C51 C50 H50 120.8 . . ?
C52 C51 C50 121.5(6) . . ?
C52 C51 H51 119.2 . . ?
C50 C51 H51 119.2 . . ?
C51 C52 C50 120.1(6) . 5_556 ?
C51 C52 H52 120.0 . . ?
C50 C52 H52 120.0 5_556 . ?
C51B C50B C52B 116.3(11) . . ?
C51B C50B H50B 121.8 . . ?
C52B C50B H50B 121.8 . . ?
C50B C51B C52B 119.4(11) . 5_556 ?
C50B C51B H51B 120.3 . . ?
C52B C51B H51B 120.3 5_556 . ?
C51B C52B C50B 124.3(11) 5_556 . ?
C51B C52B H52B 117.8 5_556 . ?
C50B C52B H52B 117.8 . . ?
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
Co1 C1 1.913(2) . ?
Co1 C32 1.943(2) . ?
Co1 C33 1.975(2) . ?
Co1 C23 2.085(3) . ?
Co1 C21 2.096(3) . ?
Co1 C24 2.097(3) . ?
Co1 C20 2.106(3) . ?
Co1 C22 2.109(3) . ?
F1 C30 1.369(3) . ?
F3 C32 1.404(3) . ?
F4 C33 1.404(2) . ?
N1 C1 1.368(3) . ?
N1 C2 1.384(3) . ?
N1 C4 1.489(3) . ?
N2 C1 1.368(3) . ?
N2 C3 1.388(3) . ?
N2 C7 1.481(3) . ?
C2 C3 1.340(4) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C6 1.514(4) . ?
C4 C5 1.527(4) . ?
C4 H4 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 1.518(4) . ?
C7 C8 1.528(4) . ?
C7 H7 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 . ?
C20 C21 1.358(6) . ?
C20 C24 1.382(6) . ?
C20 H20 1.0000 . ?
C21 C22 1.363(6) . ?
C21 H21 1.0000 . ?
C22 C23 1.400(6) . ?
C22 H22 1.0000 . ?
C23 C24 1.416(5) . ?
C23 H23 1.0000 . ?
C24 H24 1.0000 . ?
C30 C30 1.323(5) 2 ?
C30 C32 1.466(3) . ?
C32 C33 1.450(3) . ?
C33 C33 1.482(4) 2 ?
C50 C52 1.383(8) 5_556 ?
C50 C51 1.399(10) . ?
C50 H50 0.9500 . ?
C51 C52 1.371(9) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C50B C51B 1.363(15) . ?
C50B C52B 1.384(15) . ?
C50B H50B 0.9500 . ?
C51B C52B 1.373(15) 5_556 ?
C51B H51B 0.9500 . ?
C52B H52B 0.9500 . ?
