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_1558261
_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 H27 Co N4 O3, C4 H8 O'
_chemical_formula_sum            'C38 H35 Co N4 O4'
_chemical_formula_weight         670.63
_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   mixed
_audit_creation_date             2020-03-04
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-03-04 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                87.763(3)
_cell_angle_beta                 69.624(4)
_cell_angle_gamma                70.719(3)
_cell_formula_units_Z            4
_cell_length_a                   14.5135(5)
_cell_length_b                   16.2562(4)
_cell_length_c                   17.4421(8)
_cell_measurement_reflns_used    8867
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      54.8120
_cell_measurement_theta_min      3.5190
_cell_volume                     3627.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 HyPix
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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 93.00 122.00 0.50 5.00 -- 65.75 125.00 120.00 58
 2 \w -11.00 31.00 0.50 1.00 -- 0.47 94.00 10.00 84
 3 \w -93.00 -21.00 0.50 5.00 -- -64.81 94.00 10.00 144
 4 \w 46.00 126.00 0.50 5.00 -- 65.75 77.00 90.00 160
 5 \w -84.00 6.00 0.50 5.00 -- -64.81 77.00 0.00 180
 6 \w 29.00 65.00 0.50 1.00 -- 0.47 57.00 120.00 72
 7 \w -71.00 -38.00 0.50 5.00 -- -64.81 38.00-180.00 66
 8 \w -28.00 6.00 0.50 5.00 -- -64.81 38.00-180.00 68
 9 \w -11.00 23.00 0.50 1.00 -- 0.47 57.00 120.00 68
 10 \w 3.00 28.00 0.50 1.00 -- 0.47 38.00-180.00 50
 11 \w -62.00 -12.00 0.50 5.00 -- -64.81 38.00 -30.00 100
 12 \w -24.00 2.00 0.50 1.00 -- 0.47 -38.00 0.00 52
 13 \w -69.00 -44.00 0.50 1.00 -- 0.47 -38.00 0.00 50
 14 \w -136.00 -44.00 0.50 5.00 -- -64.81 -77.00 -90.00 184
 15 \w 19.00 94.00 0.50 5.00 -- 65.75 -94.00-100.00 150
 16 \w -132.00 -84.00 0.50 5.00 -- -64.81 -94.00-100.00 96
 17 \w -3.00 97.00 0.50 5.00 -- 65.75 -99.00-150.00 200
 18 \w -109.00 -83.00 0.50 5.00 -- -64.81 -99.00 0.00 52
 19 \w -137.00 -83.00 0.50 5.00 -- -64.81 -99.00-180.00 108
 20 \w -135.00 -84.00 0.50 5.00 -- -64.81 -99.00 60.00 102
 21 \w 34.00 103.00 0.50 5.00 -- 65.75-125.00-150.00 138
 22 \w 35.00 100.00 0.50 5.00 -- 65.75-125.00 150.00 130
 23 \w 36.00 63.00 0.50 5.00 -- 65.75-125.00 120.00 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SYNERGY diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0571104000
_diffrn_orient_matrix_UB_12      0.0163310000
_diffrn_orient_matrix_UB_13      -0.0617877000
_diffrn_orient_matrix_UB_21      -0.0891561000
_diffrn_orient_matrix_UB_22      -0.0260074000
_diffrn_orient_matrix_UB_23      0.0619818000
_diffrn_orient_matrix_UB_31      -0.0571378000
_diffrn_orient_matrix_UB_32      0.0959771000
_diffrn_orient_matrix_UB_33      0.0358293000
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29300
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        54.242
_diffrn_reflns_theta_max         54.242
_diffrn_reflns_theta_min         3.452
_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    4.052
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       needle
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.089
_refine_diff_density_max         1.145
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     863
_refine_ls_number_reflns         8867
_refine_ls_number_restraints     861
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0909
_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^)+(0.1262P)^2^+14.2508P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2336
_refine_ls_wR_factor_ref         0.2488
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6458
_reflns_number_total             8867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02066d2.cif
_cod_data_source_block           el-01-217
_cod_depositor_comments
;Adding full bibliography for 1558259--1558265.cif.

 Adding full bibliography for 1558259--1558265.cif.
;
_cod_original_cell_volume        3627.9(2)
_cod_database_code               1558261
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C152  H136  Co4  N14  O18  '
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     54.18
_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, All O(H,H) groups
2. Restrained distances
 C72-C71 = C70-C69
 1.52 with sigma of 0.001
 H1B-O1 = O1-H1A
 0.975 with sigma of 0.002
 H4A-O4 = O4-H4B
 0.975 with sigma of 0.002
 H1B-H1A
 1.557 with sigma of 0.005
 H4A-H4B
 1.557 with sigma of 0.005
 O7-C69 \\sim O7-C72
 with sigma of 0.002
 O6-H4A \\sim O3-H1B
 with sigma of 0.002
 Co1-H1A \\sim Co1-H1B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C71) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C70) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4. Rigid body (RIGU) restrains
 O7, C69, C70, C71, C72
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O8, C73, C74, C75, C76
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 N3, N1, O3, Co1, O1, N4, N2, C3, C27, C28, C1, C9, C11, C10, C26, C18, C2, C4,
  C31, C29, O2, C17, C12, C14, C34, C19, C7, C5, C30, C32, C16, C13, C15, C33,
 C24, C20, C8, C6, C23, C25, C21, C22
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O5, Co2, O4, N6, N7, N5, N8, C37, C44, C45, C52, C60, C35, C43, C61, C62, C36,
  C38, C48, C46, O6, C53, C68, C51, C65, C63, C41, C39, C47, C49, C54, C58, C67,
  C50, C64, C66, C40, C42, C55, C59, C57, C56
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
5.a Secondary CH2 refined with riding coordinates:
 C72(H72A,H72B), C73(H73A,H73B), C74(H74A,H74B), C76(H76A,H76B), C69(H69A,
 H69B), C75(H75A,H75B), C71(H71A,H71B), C70(H70A,H70B)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C34(H34), C13(H13), C38(H38), C46(H46), C64(H64), C40(H40),
 C28(H28), C63(H63), C12(H12), C62(H62), C45(H45), C30(H30), C39(H39), C24(H24),
  C5(H5), C68(H68), C47(H47), C67(H67), C29(H29), C17(H17), C32(H32), C4(H4),
 C51(H51), C66(H66), C33(H33), C49(H49), C58(H58), C55(H55), C16(H16), C6(H6),
 C50(H50), C15(H15), C22(H22), C23(H23), C21(H21), C57(H57), C56(H56)
5.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C42(H42A,H42B,H42C), C25(H25A,H25B,H25C), C59(H59A,H59B,H59C)
;
_shelx_res_checksum              62502
_shelx_fab_checksum              864
_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 1.494
_oxdiff_exptl_absorpt_empirical_full_min 0.541