#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:02:21 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/80/1558085.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_1558085
loop_
_publ_author_name
'Chen, Xin-Ran'
'Zhang, Shuo-Qing'
'Meyer, Tjark H.'
'Yang, Chun-Hui'
'Zhang, Qin-Hao'
'Liu, Ji-Ren'
'Xu, Hua-Jian'
'Cao, Fa-He'
'Ackermann, Lutz'
'Hong, Xin'
_publ_section_title
;
 Carboxylate breaks the arene C--H bond via a hydrogen-atom-transfer
 mechanism in electrochemical cobalt catalysis
;
_journal_issue                   22
_journal_name_full               'Chemical Science'
_journal_page_first              5790
_journal_page_last               5796
_journal_paper_doi               10.1039/D0SC01898H
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         '2(C22 H23 Co N2 O6), C H2 Cl2'
_chemical_formula_sum            'C45 H48 Cl2 Co2 N4 O12'
_chemical_formula_weight         1025.63
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-02 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.22(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.880(14)
_cell_length_b                   7.915(8)
_cell_length_c                   30.41(6)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.38
_cell_volume                     4498(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            35513
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.121
_diffrn_reflns_theta_min         2.396
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.924
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1241 before and 0.0739 after correction.
The Ratio of minimum to maximum transmission is 0.8212.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       plate
_exptl_crystal_F_000             2120
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.494
_refine_diff_density_min         -1.216
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.279
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.279
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.1113
_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)+134.7771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2499
_refine_ls_wR_factor_ref         0.2562
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4089
_reflns_number_total             4907
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc01898h2.cif
_cod_data_source_block           191128_cxr_191128_0m
_cod_depositor_comments
;Adding full bibliography for 1558085.cif.

 Adding full bibliography for 1558085.cif.
;
_cod_database_code               1558085
_shelx_shelxl_version_number     2016/6
_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_max   0.947
_shelx_estimated_absorpt_t_min   0.844
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H23A(0.5) H23B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C20(H20)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C22(H22A,H22B,
 H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.45675(6) 0.48612(13) 0.36633(4) 0.0243(3) Uani 1 1 d . . . . .
O1 O 0.4585(3) 0.5573(7) 0.30694(18) 0.0293(13) Uani 1 1 d . . . . .
O2 O 0.2465(3) 0.4483(8) 0.3638(2) 0.0378(15) Uani 1 1 d . . . . .
O3 O 0.4634(3) 0.4253(7) 0.42690(18) 0.0285(12) Uani 1 1 d . . . . .
O4 O 0.4214(3) 0.2745(7) 0.34318(19) 0.0300(13) Uani 1 1 d . . . . .
O5 O 0.5484(3) 0.3964(7) 0.36537(19) 0.0298(13) Uani 1 1 d . . . . .
O6 O 0.4885(3) 0.7056(7) 0.38589(19) 0.0287(12) Uani 1 1 d . . . . .
N1 N 0.3928(4) 0.6056(8) 0.2876(2) 0.0271(14) Uani 1 1 d . . . . .
N2 N 0.3569(3) 0.5621(8) 0.3565(2) 0.0226(13) Uani 1 1 d . . . . .
C1 C 0.3848(5) 0.6599(11) 0.2446(3) 0.0327(19) Uani 1 1 d . . . . .
H1 H 0.424796 0.656606 0.228920 0.039 Uiso 1 1 calc R . . . .
C2 C 0.3217(5) 0.7180(12) 0.2239(3) 0.037(2) Uani 1 1 d . . . . .
H2 H 0.317413 0.762428 0.194571 0.044 Uiso 1 1 calc R . . . .
C3 C 0.2622(5) 0.7104(11) 0.2472(3) 0.0340(19) Uani 1 1 d . . . . .
H3 H 0.216645 0.746319 0.232912 0.041 Uiso 1 1 calc R . . . .
C4 C 0.2689(5) 0.6522(10) 0.2903(3) 0.0305(18) Uani 1 1 d . . . . .
H4 H 0.228229 0.646465 0.305355 0.037 Uiso 1 1 calc R . . . .
C5 C 0.3374(4) 0.6004(9) 0.3120(3) 0.0240(16) Uani 1 1 d . . . . .
C6 C 0.3020(5) 0.5133(11) 0.3800(3) 0.0315(18) Uani 1 1 d . . . . .
C7 C 0.3145(5) 0.5556(10) 0.4293(3) 0.0293(18) Uani 1 1 d . . . . .
C8 C 0.3587(4) 0.6874(11) 0.4468(3) 0.0305(18) Uani 1 1 d . . . . .
H8 H 0.385570 0.748886 0.428015 0.037 Uiso 1 1 calc R . . . .
C9 C 0.3635(5) 0.7294(14) 0.4913(3) 0.042(2) Uani 1 1 d . . . . .
H9 H 0.393364 0.820225 0.502947 0.051 Uiso 1 1 calc R . . . .
C10 C 0.3253(7) 0.6396(16) 0.5188(3) 0.056(3) Uani 1 1 d . . . . .
H10 H 0.329436 0.667741 0.549454 0.068 Uiso 1 1 calc R . . . .
C11 C 0.2807(6) 0.5086(14) 0.5020(3) 0.050(3) Uani 1 1 d . . . . .
H11 H 0.254151 0.447486 0.521059 0.060 Uiso 1 1 calc R . . . .
C12 C 0.2749(5) 0.4668(12) 0.4571(3) 0.039(2) Uani 1 1 d . . . . .
H12 H 0.243997 0.377906 0.445486 0.046 Uiso 1 1 calc R . . . .
C13 C 0.4425(5) 0.2712(12) 0.4904(3) 0.0340(19) Uani 1 1 d . . . . .
H13A H 0.480837 0.344704 0.504607 0.051 Uiso 1 1 calc GR . . . .
H13B H 0.453573 0.153506 0.498697 0.051 Uiso 1 1 calc GR . . . .
H13C H 0.397142 0.303497 0.500235 0.051 Uiso 1 1 calc GR . . . .
C14 C 0.4361(4) 0.2896(10) 0.4405(3) 0.0252(16) Uani 1 1 d . . . . .
C15 C 0.4024(5) 0.1629(10) 0.4129(3) 0.0314(18) Uani 1 1 d . . . . .
H15 H 0.380108 0.073179 0.426509 0.038 Uiso 1 1 calc R . . . .
C16 C 0.3992(4) 0.1592(10) 0.3665(3) 0.0275(17) Uani 1 1 d . . . . .
C17 C 0.3692(5) 0.0055(11) 0.3408(3) 0.039(2) Uani 1 1 d . . . . .
H17A H 0.318776 0.025179 0.329010 0.059 Uiso 1 1 calc GR . . . .
H17B H 0.372961 -0.092879 0.360591 0.059 Uiso 1 1 calc GR . . . .
H17C H 0.396284 -0.015624 0.316187 0.059 Uiso 1 1 calc GR . . . .
C18 C 0.6726(5) 0.3916(12) 0.3626(3) 0.038(2) Uani 1 1 d . . . . .
H18A H 0.672197 0.276227 0.374284 0.057 Uiso 1 1 calc GR . . . .
H18B H 0.714067 0.452603 0.377964 0.057 Uiso 1 1 calc GR . . . .
H18C H 0.675522 0.387575 0.330699 0.057 Uiso 1 1 calc GR . . . .
C19 C 0.6043(4) 0.4820(11) 0.3701(2) 0.0266(16) Uani 1 1 d . . . . .
C20 C 0.6108(5) 0.6563(11) 0.3808(3) 0.0329(19) Uani 1 1 d . . . . .
H20 H 0.656761 0.707193 0.382987 0.040 Uiso 1 1 calc R . . . .
C21 C 0.5526(5) 0.7569(11) 0.3881(3) 0.0293(18) Uani 1 1 d . . . . .
C22 C 0.5649(5) 0.9421(10) 0.3989(3) 0.035(2) Uani 1 1 d . . . . .
H22A H 0.548675 1.009919 0.372346 0.053 Uiso 1 1 calc GR . . . .
H22B H 0.615970 0.962041 0.408392 0.053 Uiso 1 1 calc GR . . . .
H22C H 0.537841 0.974447 0.422767 0.053 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.42863(18) 0.0922(5) 0.22559(11) 0.0733(10) Uani 1 1 d . . . . .
C23 C 0.500000 0.2185(17) 0.250000 0.040(3) Uani 1 2 d S T P . .
H23A H 0.483661 0.291963 0.272915 0.048 Uiso 0.5 1 calc R . . . .
H23B H 0.516340 0.291952 0.227083 0.048 Uiso 0.5 1 calc R . . . .
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'
Cl Cl 0.1484 0.1585 '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'
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'
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
O1 Co1 O4 87.8(3) . . ?
O1 Co1 O6 88.8(3) . . ?
O1 Co1 N2 84.9(3) . . ?
O3 Co1 O1 174.6(3) . . ?
O3 Co1 O4 96.1(3) . . ?
O3 Co1 O6 87.4(3) . . ?
O3 Co1 N2 98.9(3) . . ?
O4 Co1 O6 175.9(3) . . ?
O4 Co1 N2 86.2(3) . . ?
O5 Co1 O1 87.5(3) . . ?
O5 Co1 O3 89.2(3) . . ?
O5 Co1 O4 86.4(3) . . ?
O5 Co1 O6 95.8(3) . . ?
O5 Co1 N2 169.5(3) . . ?
O6 Co1 N2 91.2(3) . . ?
N1 O1 Co1 111.0(4) . . ?
C14 O3 Co1 123.5(5) . . ?
C16 O4 Co1 123.8(5) . . ?
C19 O5 Co1 124.1(6) . . ?
C21 O6 Co1 124.3(5) . . ?
O1 N1 C1 118.4(7) . . ?
O1 N1 C5 118.9(7) . . ?
C1 N1 C5 122.7(7) . . ?
C5 N2 Co1 109.4(5) . . ?
C5 N2 C6 116.7(7) . . ?
C6 N2 Co1 127.2(6) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 N1 121.8(8) . . ?
C2 C1 H1 119.1 . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.6(8) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(9) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(8) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 N2 114.8(7) . . ?
N1 C5 C4 117.1(7) . . ?
N2 C5 C4 127.7(7) . . ?
O2 C6 N2 124.9(8) . . ?
O2 C6 C7 119.9(7) . . ?
N2 C6 C7 115.1(7) . . ?
C8 C7 C6 122.7(7) . . ?
C8 C7 C12 119.2(8) . . ?
C12 C7 C6 117.8(8) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.3(9) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(10) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(9) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(10) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.1(10) . . ?
C11 C12 H12 120.0 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
O3 C14 C13 115.1(7) . . ?
O3 C14 C15 125.1(8) . . ?
C15 C14 C13 119.8(7) . . ?
C14 C15 H15 117.7 . . ?
C14 C15 C16 124.6(8) . . ?
C16 C15 H15 117.7 . . ?
O4 C16 C15 125.4(8) . . ?
O4 C16 C17 114.9(7) . . ?
C15 C16 C17 119.7(7) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
O5 C19 C18 116.7(8) . . ?
O5 C19 C20 126.9(8) . . ?
C20 C19 C18 116.4(8) . . ?
C19 C20 H20 118.5 . . ?
C21 C20 C19 123.0(8) . . ?
C21 C20 H20 118.5 . . ?
O6 C21 C20 125.0(8) . . ?
O6 C21 C22 115.9(8) . . ?
C20 C21 C22 119.1(8) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl1 C23 Cl1 110.6(8) . 2_655 ?
Cl1 C23 H23A 109.5 . . ?
Cl1 C23 H23A 109.5 2_655 . ?
Cl1 C23 H23B 109.5 . . ?
Cl1 C23 H23B 109.5 2_655 . ?
H23A C23 H23B 108.1 . . ?
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 O1 1.897(7) . ?
Co1 O3 1.891(7) . ?
Co1 O4 1.901(6) . ?
Co1 O5 1.875(6) . ?
Co1 O6 1.905(6) . ?
Co1 N2 1.960(7) . ?
O1 N1 1.349(9) . ?
O2 C6 1.208(10) . ?
O3 C14 1.285(9) . ?
O4 C16 1.263(10) . ?
O5 C19 1.244(9) . ?
O6 C21 1.269(10) . ?
N1 C1 1.364(11) . ?
N1 C5 1.365(10) . ?
N2 C5 1.384(11) . ?
N2 C6 1.396(10) . ?
C1 H1 0.9500 . ?
C1 C2 1.347(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.415(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(13) . ?
C4 H4 0.9500 . ?
C4 C5 1.427(11) . ?
C6 C7 1.520(12) . ?
C7 C8 1.393(12) . ?
C7 C12 1.396(12) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(12) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(14) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C14 1.513(12) . ?
C14 C15 1.401(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.404(12) . ?
C16 C17 1.512(11) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C19 1.521(12) . ?
C19 C20 1.419(12) . ?
C20 H20 0.9500 . ?
C20 C21 1.401(12) . ?
C21 C22 1.512(11) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Cl1 C23 1.755(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
