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_1558260
_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         'C34 H24 Co N4 O2'
_chemical_formula_sum            'C34 H24 Co N4 O2'
_chemical_formula_weight         579.50
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-20
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2018.05.31 svn.r3508 for OlexSys, GUI svn.r5510)
;
_audit_update_record
;
2018-06-20 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.257(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1539(3)
_cell_length_b                   16.6946(4)
_cell_length_c                   14.6989(3)
_cell_measurement_reflns_used    5274
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.8710
_cell_measurement_theta_min      4.0150
_cell_volume                     2701.43(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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     50.00  77.00   0.50    5.05    --   18.43  57.00  30.00   54
  2  \w      1.00  42.00   0.50    5.05    --   18.43  57.00  30.00   82
  3  \w     68.00 138.00   0.50   20.20    --  110.00 164.00 -26.00  140
  4  \w    120.00 147.00   0.50   20.20    --  110.00 116.00-174.00   54
  5  \w    135.00 136.00   0.50   20.20    --  110.00  30.00 -60.00    2
  6  \w    105.00 177.00   0.50   20.20    --  110.00  30.00   0.00  144
  7  \w    115.00 140.00   0.50   12.00    --  110.00-166.00 -48.00   50
  8  \w    -92.00 -40.00   0.50    5.05    --  -18.43-178.00  90.00  104
  9  \w    -55.00   7.00   0.50    5.05    --  -18.43 -77.00-150.00  124
 10  \w    -89.00 -40.00   0.50    5.05    --  -18.43-178.00-120.00   98
 11  \w      1.00  46.00   0.50    5.05    --   18.43  57.00-180.00   90
 12  \w   -161.00 -66.00   0.50   12.00    --  -88.50 -15.00  90.00  190
 13  \w    -99.00 -42.00   0.50   12.00    --  -88.50  45.00-180.00  114
 14  \w     45.00 106.00   0.50   12.00    --  110.00 -95.00 120.00  122
 15  \w     40.00  76.00   0.50   12.00    --  110.00-125.00 -30.00   72
 16  \w     43.00  69.00   0.50   12.00    --  110.00 -61.00  60.00   52
 17  \w    127.00 178.00   0.50   12.00    --  110.00 125.00-150.00  102
 18  \w    127.00 177.00   0.50   12.00    --  110.00  61.00-180.00  100
 19  \w     40.00 125.00   0.50   12.00    --  110.00 -61.00-120.00  170
 20  \w     87.00 130.00   0.50   12.00    --  110.00 -61.00  60.00   86
;
_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      -0.0218553000
_diffrn_orient_matrix_UB_12      -0.0722194000
_diffrn_orient_matrix_UB_13      -0.0658190000
_diffrn_orient_matrix_UB_21      0.0073166000
_diffrn_orient_matrix_UB_22      0.0556382000
_diffrn_orient_matrix_UB_23      -0.0826040000
_diffrn_orient_matrix_UB_31      0.1379527000
_diffrn_orient_matrix_UB_32      -0.0144484000
_diffrn_orient_matrix_UB_33      0.0112657000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11024
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        65.069
_diffrn_reflns_theta_max         65.069
_diffrn_reflns_theta_min         4.016
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    5.297
_exptl_absorpt_correction_T_max  0.69716
_exptl_absorpt_correction_T_min  0.67847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       needle
_exptl_crystal_F_000             1196
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4486
_refine_ls_number_restraints     375
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1079P)^2^+1.3749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1669
_refine_ls_wR_factor_ref         0.1800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3700
_reflns_number_total             4486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02066d2.cif
_cod_data_source_block           el-01-86a
_cod_depositor_comments
;Adding full bibliography for 1558259--1558265.cif.

 Adding full bibliography for 1558259--1558265.cif.
;
_cod_original_cell_volume        2701.42(11)
_cod_database_code               1558260
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C136 H96 Co4 N16 O8'
_reflns_odcompleteness_completeness 96.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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(C12) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3. Rigid body (RIGU) restrains
 C5, C4
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C5, C6
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C6, C7
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C7, C8
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C8, N2
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 N2, C10
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C10, O1
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C10, C11
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C11, C12
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C12, C17
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C12, C13
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C13, C14
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C14, C15
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C15, C16
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C16, C33
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C33, C32, C31, C30, C29, C28, C27, C34
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C28, C27, O2, N4
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 N4, C25, C26, C21, C22, C23, C24
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 N3, C18, C19, C20, C21, C26, C25
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 N1, C9, C8, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C9, C4
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C9, N1
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C9, C8
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C4, C9
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
 C12, Co1, N1, N3, N4, N2, C9, C1, C26, C18, C27, C25, C8, C10, C4, C2, C21,
 C19, O2, C28, C24, C7, O1, C11, C3, C5, C22, C20, C33, C29, C23, C6, C16, C32,
 C34, C30, C17, C13, C15, C31, C14
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0002
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C22(H22), C18(H18), C32(H32), C3(H3), C6(H6), C15(H15), C31(H31),
 C5(H5), C14(H14), C13(H13), C23(H23), C2(H2), C7(H7), C20(H20), C24(H24),
 C30(H30), C19(H19)
4.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C)
;
_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-01-86A
_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 6.063
_oxdiff_exptl_absorpt_empirical_full_min 0.149