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_1558263
_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         'C27 H31 Co N2 O5, C24 H20 P, C4 H10 O'
_chemical_formula_sum            'C55 H61 Co N2 O6 P'
_chemical_formula_weight         935.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-31
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2017.10.03 svn.r3461 for OlexSys, GUI svn.r5395)
;
_audit_update_record
;
2020-03-04 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.0538(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.10757(17)
_cell_length_b                   22.2355(3)
_cell_length_c                   16.9979(2)
_cell_measurement_reflns_used    41192
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      38.2400
_cell_measurement_theta_min      1.8160
_cell_volume                     4862.18(11)
_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 (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      101(2)
_diffrn_detector                 HyPix
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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 23.00 48.50 0.50 13.84 -- 22.26-142.00 -3.00 51 2 \w 35.00 61.50 0.50 13.84 -- 22.26-128.00 168.00 53 3 \w 11.00 86.50 0.50 13.84 -- 22.26 57.00 0.00 151 4 \w 3.00 93.50 0.50 13.84 -- 22.26 77.00 90.00 181 5 \w 43.00 69.50 0.50 13.84 -- 22.26 178.00 -30.00 53 6 \w 39.00 92.50 0.50 13.84 -- 22.26 178.00 120.00 107 7 \w -48.00 9.00 0.50 13.84 -- 22.26 -38.00 -90.00 114 8 \w -90.00 -6.50 0.50 13.84 -- -22.26 -77.00-150.00 167 9 \w -87.00 -54.50 0.50 13.84 -- -22.26 -38.00 -60.00 65'
_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      0.0233395000
_diffrn_orient_matrix_UB_12      -0.0285358000
_diffrn_orient_matrix_UB_13      0.0095435000
_diffrn_orient_matrix_UB_21      -0.0485010000
_diffrn_orient_matrix_UB_22      -0.0141642000
_diffrn_orient_matrix_UB_23      -0.0141967000
_diffrn_orient_matrix_UB_31      0.0118808000
_diffrn_orient_matrix_UB_32      -0.0018125000
_diffrn_orient_matrix_UB_33      -0.0389223000
_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  0.0494
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            97339
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.318
_diffrn_reflns_theta_min         1.804
_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    0.438
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.460
_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            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       prism
_exptl_crystal_F_000             1980
_exptl_crystal_recrystallization_method
'Layering of diethyl ether with a concentrated solution of the sample in acetonitrile'
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.294
_exptl_crystal_size_min          0.178
_refine_diff_density_max         1.520
_refine_diff_density_min         -1.487
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         23500
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+1.9087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18590
_reflns_number_total             23500
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02066d2.cif
_cod_data_source_block           el-01-180
_cod_depositor_comments
;Adding full bibliography for 1558259--1558265.cif.

 Adding full bibliography for 1558259--1558265.cif.
;
_cod_original_cell_volume        4862.18(12)
_cod_database_code               1558263
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C216 H232 Co4 N8 O24 S4 '
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.23
_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. Restrained distances
 C2S_2-C1S_2
 1.518 with sigma of 0.002
 C1S_2-C3S_2
 2.374 with sigma of 0.008
 C4S_1-C3S_1
 1.518 with sigma of 0.005
 O1S_1-C3S_1 = O1S_1-C1S_1
 O1S_2-C3S_2 = O1S_2-C1S_2
 1.419 with sigma of 0.002
 C1S_1-C3S_1
 C1S_2-C3S_2
 2.374 with sigma of 0.004
 C2S_2-C1S_2 \\sim C4S_2-C3S_2
 with sigma of 0.002
 O1S_1-C3S_1 \\sim O1S_1-C1S_1
 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C3S_2) \\sim Ueq, Uanis(C1S_2) \\sim Ueq: with sigma of 0.002 and sigma
for terminal atoms of 0.004
Uanis(C1S_1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C4S_1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(O1S_1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
Uanis(C3S_2) = Uanis(C3S_1)
Uanis(O1S_1) = Uanis(O1S_2)
Uanis(C1S_2) = Uanis(C1S_1)
Uanis(C2S_1) = Uanis(C2S_2)
Uanis(C4S_1) = Uanis(C4S_2)
4. Rigid body (RIGU) restrains
 C10, C11, C12, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C1S_2, C2S_2
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C3S_2, C4S_2
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O1S_2, C1S_2, C3S_2
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O1S_1, C1S_1, C2S_1, C3S_1, C4S_1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O1S_1, C1S_1, C2S_1, C3S_1, C4S_1, H2SA_1, H2SB_1, H2SC_1, H4SA_1, H4SB_1,
 H4SC_1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1S_1, C2S_1
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C3S_1, C4S_1
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 O1S_1, C1S_1, C3S_1
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C1S_1, C3S_1, O1S_2, C2S_2, C4S_2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Same fragment restrains
{O1S_2, C1S_2, C2S_2, C3S_2, C4S_2}
as
{O1S_1, C1S_1, C2S_1, C3S_1, C4S_1} sigma for 1-2: 0.002 1-3: 0.004
6. Others
 Sof(O1S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=
 Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(H4SC)=1-FVAR(1)
 Sof(O1S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=
 Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(H4SC)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C3S(H3SA,H3SB), C1S(H1SA,H1SB), C3S(H3SA,H3SB)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C48(H48), C49(H49),
  C50(H50), C51(H51), C52(H52), C54(H54), C55(H55), C56(H56), C57(H57),
 C58(H58), C60(H60), C61(H61), C62(H62), C63(H63), C64(H64)
7.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C33(H33A,H33B,
 H33C), C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C2S(H2SA,
 H2SB,H2SC), C4S(H4SA,H4SB,H4SC), C2S(H2SA,H2SB,H2SC), C4S(H4SA,H4SB,H4SC)
;
_shelx_res_checksum              91277
_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-01-180
_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.792