Mechanistic details of the cobalt-mediated dehydrogenative dimerization of aminoquinoline-directed benzamides.
Xu, Li-Ping; Liu, Elaine E. L.-N.; Bacsa, John; MacBeth, Cora E.; Musaev, Djamaladdin G.; Chemical science 11 (2020) 6085–6096; doi:10.1039/d0sc02066d

data_1558265
_publ_section_title
;
 Mechanistic details of the cobalt-mediated dehydrogenative dimerization
 of aminoquinoline-directed benzamides.
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              6085
_journal_page_last               6096
_journal_paper_doi               10.1039/d0sc02066d
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C39 H33 Co N4 O4, 1(C6 H6)'
_chemical_formula_sum            'C45 H39 Co N4 O4'
_chemical_formula_weight         758.73
_chemical_properties_physical    Air-sensitive
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-09
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2018.05.31 svn.r3508 for OlexSys, GUI svn.r5510)
;
_audit_update_record
;
2020-03-04 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                77.378(2)
_cell_angle_beta                 74.686(2)
_cell_angle_gamma                89.375(2)
_cell_formula_units_Z            2
_cell_length_a                   10.9148(2)
_cell_length_b                   12.2160(2)
_cell_length_c                   14.5150(3)
_cell_measurement_reflns_used    39960
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.1140
_cell_measurement_theta_min      1.7210
_cell_volume                     1819.28(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 HyPix
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -21.00  44.00   0.50   20.00    --  -29.66  38.00 -30.00  130
  2  \w      1.00 104.00   0.50   20.00    --   29.51  77.00 -90.00  206
  3  \w     62.00  88.00   0.50   20.00    --   29.51 178.00   0.00   52
  4  \w     39.00 108.00   0.50   20.00    --   29.51 178.00  90.00  138
  5  \w      1.00 104.00   0.50   20.00    --   29.51  77.00 -60.00  206
  6  \w     -6.00  72.00   0.50   20.00    --   29.51-105.00  65.00  156
  7  \w    -48.00  44.00   0.50   20.00    --   29.51 -38.00  30.00  184
  8  \w    -48.00  52.00   0.50   20.00    --   29.51 -38.00 120.00  200
  9  \w    -46.00  -2.00   0.50   20.00    --  -29.66 -77.00-120.00   88
 10  \w    -26.00  69.00   0.50   20.00    --   29.51 -99.00-180.00  190
 11  \w    -72.00 -15.00   0.50   20.00    --  -29.66 105.00 165.00  114
 12  \w   -108.00 -82.00   0.50   20.00    --  -29.66 178.00 -30.00   52
 13  \w   -104.00 -82.50   0.50   20.00    --  -29.66 178.00-150.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0513771000
_diffrn_orient_matrix_UB_12      0.0031519000
_diffrn_orient_matrix_UB_13      -0.0217323000
_diffrn_orient_matrix_UB_21      -0.0427857000
_diffrn_orient_matrix_UB_22      0.0040124000
_diffrn_orient_matrix_UB_23      0.0452294000
_diffrn_orient_matrix_UB_31      0.0089877000
_diffrn_orient_matrix_UB_32      0.0593561000
_diffrn_orient_matrix_UB_33      -0.0135685000
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            58610
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.318
_diffrn_reflns_theta_min         1.710
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.601
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of diethyl ether and benzene  by solvent layering'
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.182
_refine_diff_density_max         2.096
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         17570
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.6963P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15583
_reflns_number_total             17570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02066d2.cif
_cod_data_source_block           el-01-82
_cod_depositor_comments
;Adding full bibliography for 1558259--1558265.cif.

 Adding full bibliography for 1558259--1558265.cif.
;
_cod_database_code               1558265
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C90 H78 Co2 N8 O8'
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.23
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C40B) \\sim Ueq, Uanis(C41A) \\sim Ueq, Uanis(C42A) \\sim Ueq,
Uanis(C44A) \\sim Ueq, Uanis(C43A) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(C43B) = Uanis(C43A)
3. Rigid body (RIGU) restrains
 C45A, C40A, C41A, C42A, C44A, C43A
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C45B, C40B, C41B, C42B, C44B, C43B
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
4. Same fragment restrains
{C40B, C41B, C42B, C43B, C44B, C45B} sigma for 1-2: 0.002, 1-3: 0.002
as
{C40A, C41A, C42A, C43A, C44A, C45A}
5. Others
 Sof(C40B)=Sof(H40B)=Sof(C41B)=Sof(H41B)=Sof(C42B)=Sof(H42B)=Sof(C43B)=
 Sof(H43B)=Sof(C44B)=Sof(H44B)=Sof(C45B)=Sof(H45B)=1-FVAR(1)
 Sof(C40A)=Sof(H40A)=Sof(C41A)=Sof(H41A)=Sof(C42A)=Sof(H42A)=Sof(C43A)=
 Sof(H43A)=Sof(C44A)=Sof(H44A)=Sof(C45A)=Sof(H45A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C28(H28), C40A(H40A), C41A(H41A), C42A(H42A), C43A(H43A), C44A(H44A),
 C45A(H45A), C20(H20), C40B(H40B), C41B(H41B), C42B(H42B), C43B(H43B),
 C44B(H44B), C45B(H45B), C1(H1), C2(H2), C3(H3), C19(H19), C5(H5), C21(H21),
 C6(H6), C7(H7), C27(H27), C29(H29), C31(H31), C33(H33), C13(H13), C14(H14),
 C15(H15), C32(H32)
6.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C38(H38A,H38B,H38C), C17(H17A,H17B,H17C), C37(H37A,H37B,
 H37C), C39(H39A,H39B,H39C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id EL-01-82
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.804