#------------------------------------------------------------------------------
#$Date: 2020-10-06 08:47:45 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257208 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/75/1557595.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_1557595
loop_
_publ_author_name
'Anandababu, Karunanithi'
'Muthuramalingam, Sethuraman'
'Velusamy, Marappan'
'Mayilmurugan, Ramasamy'
_publ_section_title
;
 Single-step benzene hydroxylation by cobalt(ii) catalysts via a
 cobalt(iii)-hydroperoxo intermediate
;
_journal_issue                   8
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              2540
_journal_page_last               2548
_journal_paper_doi               10.1039/C9CY02601K
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C17 H22 Cl2 Co N4 O4'
_chemical_formula_weight         476.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2019-09-18 deposited with the CCDC.	2020-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.779(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2832(8)
_cell_length_b                   7.3066(5)
_cell_length_c                   22.5865(14)
_cell_measurement_temperature    293(2)
_cell_volume                     2016.8(2)
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7540
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.326
_exptl_absorpt_coefficient_mu    1.147
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             980
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.064
_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     253
_refine_ls_number_reflns         4104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0475
_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)+(0.0539P)²+1.9203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3333
_reflns_number_total             4104
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cy02601k2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
;Adding full bibliography for 1557594--1557597.cif.

 Adding full bibliography for 1557594--1557597.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1557595
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.28411(3) 0.08469(6) 0.37140(2) 0.03413(15) Uani 1 1 d . . . . .
Cl1 Cl 0.42895(8) -0.10445(12) 0.38770(4) 0.0545(3) Uani 1 1 d . . . . .
C12 C 0.4313(3) 0.3942(5) 0.39183(15) 0.0461(8) Uani 1 1 d . . . . .
H12A H 0.4993 0.3267 0.3995 0.055 Uiso 1 1 calc R U . . .
H12B H 0.4442 0.5191 0.4052 0.055 Uiso 1 1 calc R U . . .
C3 C 0.0146(4) -0.3652(6) 0.3065(2) 0.0740(13) Uani 1 1 d . . . . .
H3 H -0.0368 -0.4570 0.2973 0.089 Uiso 1 1 calc R U . . .
C9 C 0.3936(3) 0.2514(6) 0.48460(15) 0.0549(10) Uani 1 1 d . . . . .
H9A H 0.4299 0.3543 0.5053 0.066 Uiso 1 1 calc R U . . .
H9B H 0.4480 0.1570 0.4807 0.066 Uiso 1 1 calc R U . . .
N3 N 0.3473(2) 0.3107(4) 0.42472(11) 0.0371(6) Uani 1 1 d . . . . .
C2 C 0.1020(4) -0.3458(6) 0.27383(19) 0.0642(11) Uani 1 1 d . . . . .
H2 H 0.1103 -0.4227 0.2418 0.077 Uiso 1 1 calc R U . . .
C4 C 0.0036(3) -0.2492(6) 0.3525(2) 0.0691(12) Uani 1 1 d . . . . .
H4 H -0.0557 -0.2605 0.3748 0.083 Uiso 1 1 calc R U . . .
N2 N 0.1689(2) 0.1256(4) 0.43306(13) 0.0497(7) Uani 1 1 d . . . . .
C15 C 0.4032(4) 0.5008(6) 0.22747(19) 0.0665(12) Uani 1 1 d . . . . .
H15 H 0.4303 0.5814 0.2007 0.080 Uiso 1 1 calc R U . . .
C14 C 0.4365(3) 0.5142(5) 0.28704(18) 0.0564(10) Uani 1 1 d . . . . .
H14 H 0.4864 0.6038 0.3010 0.068 Uiso 1 1 calc R U . . .
C16 C 0.3302(4) 0.3687(6) 0.20779(16) 0.0616(11) Uani 1 1 d . . . . .
H16 H 0.3072 0.3571 0.1675 0.074 Uiso 1 1 calc R U . . .
C5 C 0.0805(3) -0.1150(5) 0.36602(17) 0.0490(9) Uani 1 1 d . . . . .
N1 N 0.1668(2) -0.0965(4) 0.33460(12) 0.0415(6) Uani 1 1 d . . . . .
C11 C 0.1488(3) 0.3236(6) 0.43500(18) 0.0612(11) Uani 1 1 d . . . . .
H11A H 0.1213 0.3546 0.4725 0.073 Uiso 1 1 calc R U . . .
H11B H 0.0932 0.3565 0.4032 0.073 Uiso 1 1 calc R U . . .
C13 C 0.3953(3) 0.3931(4) 0.32627(15) 0.0385(7) Uani 1 1 d . . . . .
N4 N 0.3232(2) 0.2648(4) 0.30710(11) 0.0359(6) Uani 1 1 d . . . . .
C7 C 0.2221(4) 0.0548(7) 0.49009(19) 0.0699(13) Uani 1 1 d . . . . .
H7A H 0.2561 -0.0618 0.4828 0.084 Uiso 1 1 calc R U . . .
H7B H 0.1662 0.0325 0.5166 0.084 Uiso 1 1 calc R U . . .
C6 C 0.0692(4) 0.0202(8) 0.4144(2) 0.0842(16) Uani 1 1 d . . . . .
H6A H 0.0111 0.1052 0.4012 0.101 Uiso 1 1 calc R U . . .
H6B H 0.0471 -0.0445 0.4487 0.101 Uiso 1 1 calc R U . . .
C1 C 0.1766(3) -0.2109(5) 0.28936(16) 0.0500(9) Uani 1 1 d . . . . .
H1 H 0.2366 -0.1984 0.2676 0.060 Uiso 1 1 calc R U . . .
C17 C 0.2913(3) 0.2530(5) 0.24861(14) 0.0470(8) Uani 1 1 d . . . . .
H17 H 0.2411 0.1631 0.2353 0.056 Uiso 1 1 calc R U . . .
C10 C 0.2524(3) 0.4328(5) 0.42839(16) 0.0499(9) Uani 1 1 d . . . . .
H10A H 0.2419 0.5072 0.3927 0.060 Uiso 1 1 calc R U . . .
H10B H 0.2669 0.5142 0.4622 0.060 Uiso 1 1 calc R U . . .
C8 C 0.3064(4) 0.1787(7) 0.52050(17) 0.0710(13) Uani 1 1 d . . . . .
H8A H 0.3424 0.1136 0.5544 0.085 Uiso 1 1 calc R U . . .
H8B H 0.2689 0.2825 0.5359 0.085 Uiso 1 1 calc R U . . .
Cl2 Cl 0.21087(8) -0.33780(14) 0.60615(4) 0.0544(3) Uani 1 1 d . . . . .
O2 O 0.1328(4) -0.3839(8) 0.5585(2) 0.147(2) Uani 1 1 d . . . . .
O4 O 0.3009(3) -0.2930(9) 0.5788(3) 0.169(3) Uani 1 1 d . . . . .
O1 O 0.1722(5) -0.1849(9) 0.6321(2) 0.180(3) Uani 1 1 d . . . . .
O3 O 0.2304(7) -0.4743(10) 0.6433(3) 0.227(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'
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
N4 Co1 N1 109.22(11) . . ?
N4 Co1 N2 126.73(12) . . ?
N1 Co1 N2 82.48(11) . . ?
N4 Co1 N3 78.82(10) . . ?
N1 Co1 N3 156.53(11) . . ?
N2 Co1 N3 75.42(11) . . ?
N4 Co1 Cl1 105.77(8) . . ?
N1 Co1 Cl1 100.36(8) . . ?
N2 Co1 Cl1 123.46(10) . . ?
N3 Co1 Cl1 98.36(8) . . ?
N3 C12 C13 110.2(3) . . ?
N3 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
N3 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
N3 C9 C8 111.5(3) . . ?
N3 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N3 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C12 N3 C10 112.2(3) . . ?
C12 N3 C9 111.1(3) . . ?
C10 N3 C9 111.0(3) . . ?
C12 N3 Co1 105.65(19) . . ?
C10 N3 Co1 104.7(2) . . ?
C9 N3 Co1 111.9(2) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C11 N2 C6 112.7(4) . . ?
C11 N2 C7 112.3(3) . . ?
C6 N2 C7 110.4(4) . . ?
C11 N2 Co1 106.6(2) . . ?
C6 N2 Co1 109.4(2) . . ?
C7 N2 Co1 105.1(2) . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C14 C13 119.4(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C15 C16 C17 118.7(4) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
N1 C5 C4 121.1(4) . . ?
N1 C5 C6 117.3(3) . . ?
C4 C5 C6 121.6(4) . . ?
C1 N1 C5 118.7(3) . . ?
C1 N1 Co1 126.5(2) . . ?
C5 N1 Co1 114.1(2) . . ?
N2 C11 C10 111.6(3) . . ?
N2 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N4 C13 C14 121.1(3) . . ?
N4 C13 C12 116.4(3) . . ?
C14 C13 C12 122.5(3) . . ?
C13 N4 C17 118.9(3) . . ?
C13 N4 Co1 114.6(2) . . ?
C17 N4 Co1 126.1(2) . . ?
N2 C7 C8 114.5(4) . . ?
N2 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
N2 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N2 C6 C5 114.9(3) . . ?
N2 C6 H6A 108.5 . . ?
C5 C6 H6A 108.5 . . ?
N2 C6 H6B 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
N1 C1 C2 122.5(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
N4 C17 C16 122.3(4) . . ?
N4 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
N3 C10 C11 111.2(3) . . ?
N3 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
N3 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C7 C8 C9 117.8(3) . . ?
C7 C8 H8A 107.9 . . ?
C9 C8 H8A 107.9 . . ?
C7 C8 H8B 107.9 . . ?
C9 C8 H8B 107.9 . . ?
H8A C8 H8B 107.2 . . ?
O3 Cl2 O4 111.7(4) . . ?
O3 Cl2 O1 113.3(5) . . ?
O4 Cl2 O1 109.4(5) . . ?
O3 Cl2 O2 112.0(5) . . ?
O4 Cl2 O2 103.4(4) . . ?
O1 Cl2 O2 106.5(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
Co1 N4 2.053(3) . ?
Co1 N1 2.069(3) . ?
Co1 N2 2.104(3) . ?
Co1 N3 2.143(3) . ?
Co1 Cl1 2.2536(10) . ?
C12 N3 1.464(4) . ?
C12 C13 1.502(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C3 C4 1.358(6) . ?
C3 C2 1.370(6) . ?
C3 H3 0.9300 . ?
C9 N3 1.478(4) . ?
C9 C8 1.504(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N3 C10 1.476(4) . ?
C2 C1 1.368(5) . ?
C2 H2 0.9300 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
N2 C11 1.469(5) . ?
N2 C6 1.472(5) . ?
N2 C7 1.478(5) . ?
C15 C16 1.361(6) . ?
C15 C14 1.370(6) . ?
C15 H15 0.9300 . ?
C14 C13 1.384(5) . ?
C14 H14 0.9300 . ?
C16 C17 1.372(5) . ?
C16 H16 0.9300 . ?
C5 N1 1.341(4) . ?
C5 C6 1.489(6) . ?
N1 C1 1.335(4) . ?
C11 C10 1.523(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 N4 1.331(4) . ?
N4 C17 1.342(4) . ?
C7 C8 1.491(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C1 H1 0.9300 . ?
C17 H17 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
Cl2 O3 1.311(5) . ?
Cl2 O4 1.360(4) . ?
Cl2 O1 1.369(5) . ?
Cl2 O2 1.409(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C12 N3 C10 -74.8(3) . . . . ?
C13 C12 N3 C9 160.2(3) . . . . ?
C13 C12 N3 Co1 38.7(3) . . . . ?
C8 C9 N3 C12 175.6(3) . . . . ?
C8 C9 N3 C10 50.1(4) . . . . ?
C8 C9 N3 Co1 -66.5(4) . . . . ?
C4 C3 C2 C1 1.0(7) . . . . ?
C2 C3 C4 C5 -0.5(7) . . . . ?
C16 C15 C14 C13 0.0(6) . . . . ?
C14 C15 C16 C17 0.5(6) . . . . ?
C3 C4 C5 N1 -0.2(7) . . . . ?
C3 C4 C5 C6 177.4(5) . . . . ?
C4 C5 N1 C1 0.4(6) . . . . ?
C6 C5 N1 C1 -177.3(4) . . . . ?
C4 C5 N1 Co1 -170.3(3) . . . . ?
C6 C5 N1 Co1 12.1(5) . . . . ?
C6 N2 C11 C10 -156.1(3) . . . . ?
C7 N2 C11 C10 78.5(4) . . . . ?
Co1 N2 C11 C10 -36.0(4) . . . . ?
C15 C14 C13 N4 -0.5(6) . . . . ?
C15 C14 C13 C12 177.5(4) . . . . ?
N3 C12 C13 N4 -25.0(4) . . . . ?
N3 C12 C13 C14 156.9(3) . . . . ?
C14 C13 N4 C17 0.6(5) . . . . ?
C12 C13 N4 C17 -177.5(3) . . . . ?
C14 C13 N4 Co1 174.4(3) . . . . ?
C12 C13 N4 Co1 -3.7(4) . . . . ?
C11 N2 C7 C8 -38.6(5) . . . . ?
C6 N2 C7 C8 -165.3(4) . . . . ?
Co1 N2 C7 C8 76.9(4) . . . . ?
C11 N2 C6 C5 130.2(4) . . . . ?
C7 N2 C6 C5 -103.3(5) . . . . ?
Co1 N2 C6 C5 11.8(5) . . . . ?
N1 C5 C6 N2 -16.4(6) . . . . ?
C4 C5 C6 N2 166.0(4) . . . . ?
C5 N1 C1 C2 0.1(5) . . . . ?
Co1 N1 C1 C2 169.5(3) . . . . ?
C3 C2 C1 N1 -0.8(6) . . . . ?
C13 N4 C17 C16 -0.2(5) . . . . ?
Co1 N4 C17 C16 -173.1(3) . . . . ?
C15 C16 C17 N4 -0.4(6) . . . . ?
C12 N3 C10 C11 153.2(3) . . . . ?
C9 N3 C10 C11 -81.8(4) . . . . ?
Co1 N3 C10 C11 39.1(3) . . . . ?
N2 C11 C10 N3 -2.8(4) . . . . ?
N2 C7 C8 C9 -50.6(6) . . . . ?
N3 C9 C8 C7 43.1(5) . . . . ?
