Activator-free single-component Co(i)-catalysts for regio- and enantioselective heterodimerization and hydroacylation reactions of 1,3-dienes. New reduction procedures for synthesis of [L]Co(i)-complexes and comparison to in situ generated catalysts
Parsutkar, Mahesh M.; Moore, Curtis E.; RajanBabu, T. V.; Dalton Transactions  (2022) –; doi:10.1039/D2DT01484J

data_7710553
_publ_section_title
;
 Activator-free single-component Co(i)-catalysts for regio- and
 enantioselective heterodimerization and hydroacylation reactions of
 1,3-dienes. New reduction procedures for synthesis of [L]Co(i)-complexes
 and comparison to in situ generated catalysts
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01484J
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H28 Co D6 N2 P2, C32 H12 B F24'
_chemical_formula_sum            'C56 H40 B Co D6 F24 N2 P2'
_chemical_formula_weight         1340.66
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-07-13
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2020-07-13 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                106.052(2)
_cell_angle_beta                 102.166(2)
_cell_angle_gamma                111.9630(10)
_cell_formula_units_Z            2
_cell_length_a                   13.7516(7)
_cell_length_b                   14.4882(7)
_cell_length_c                   17.3962(9)
_cell_measurement_reflns_used    9716
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.348
_cell_measurement_theta_min      2.933
_cell_volume                     2890.8(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 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_temperature      100.0
_diffrn_detector                 'Bruker Photon II area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Curved-Graphite, Bruker TRIUMPH'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            124192
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.433
_diffrn_reflns_theta_min         2.915
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              fine-focus
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_T_max  0.0932
_exptl_absorpt_correction_T_min  0.0678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0632 before and 0.0606 after correction.
The Ratio of minimum to maximum transmission is 0.7275.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Purple
_exptl_crystal_colour_primary    Purple
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       Block
_exptl_crystal_F_000             1348
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 9458 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1662
_refine_ls_number_reflns         23621
_refine_ls_number_restraints     156
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0319P)^2^+1.1261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0763
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                21042
_reflns_number_total             23621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01484j2.cif
_cod_data_source_block           RBabu_MP-05-156
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7710553
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.866
_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. Restrained distances
 F6B-C32' = F5C-C32' = F6'-C32' = F5B-C32' = F4'-C32' = F5D-C32' = F4B-C32' =
 F5'-C32'
 1.3 with sigma of 0.02
 F6B-F4B
 2.1 with sigma of 0.02
 F4'-F5'
 2.1 with sigma of 0.02
 F6B-F5B
 2.1 with sigma of 0.02
 F6'-F4'
 2.1 with sigma of 0.02
 F6'-F5'
 2.1 with sigma of 0.02
 F4B-F5B
 2.1 with sigma of 0.02
 F3-C31 = F3A-C31 = F2-C31 = F2A-C31 = F1-C31 = F1A-C31
 1.3 with sigma of 0.02
 F3A-F2A
 2.1 with sigma of 0.02
 F1A-F2A
 2.1 with sigma of 0.02
 F3-F1
 2.1 with sigma of 0.02
 F2-F3
 2.1 with sigma of 0.02
 F2-F1
 2.1 with sigma of 0.02
 F1A-F3A
 2.1 with sigma of 0.02
 F14A-F15A
 2.1 with sigma of 0.02
 F15-F14
 2.1 with sigma of 0.02
 F15A-C47 = F15-C47 = F13A-C47 = F13-C47 = F14-C47 = F14A-C47
 1.3 with sigma of 0.02
 F13A-F14A
 2.1 with sigma of 0.02
 F15A-F13A
 2.1 with sigma of 0.02
 F15-F13
 2.1 with sigma of 0.02
 F14-F13
 2.1 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F5C) = Uanis(F5D)
Uanis(F5B) = Uanis(F5')
4. Rigid body (RIGU) restrains
 F4', F5', F6', F4B, F5B, F6B, F5D, F5C, C32'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F1, F2, F3, C31, F3A, F1A, F2A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F13, F14, F15, C47, F14A, F15A, F13A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 1*[Sof(F6B)]+1*[Sof(F5')]+1*[Sof(F4')]+1*[Sof(F5C)]+1*[Sof(F4B)]+1*[Sof(F6')]+
 1*[Sof(F5B)]+1*[Sof(F5D)]=3 with esd of 0
 Sof(F3A)=Sof(F1A)=Sof(F2A)=1-FVAR(9)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(9)
 Sof(F14A)=Sof(F15A)=Sof(F13A)=1-FVAR(10)
 Sof(F13)=Sof(F14)=Sof(F15)=FVAR(10)
6.a Aromatic/amide H refined with riding coordinates:
 C1(D1), C2(D2), C3(D3), C4(D4), C5(D5), C6(D6), C21(H21), C22(H22), C23(H23),
 C24(H24), C1'(D1'), C2'(D2'), C3'(D3'), C4'(D4'), C5'(D5'), C6'(D6'),
 C21'(H21'), C22'(H22'), C23'(H23'), C24'(H24'), C26(H26), C28(H28), C30(H30),
 C34(H34), C36(H36), C38(H38), C42(H42), C44(H44), C46(H46), C50(H50), C52(H52),
  C54(H54), C26'(H26'), C28'(H28'), C30'(H30'), C34'(H34'), C36'(H36'),
 C38'(H38'), C42'(H42'), C44'(H44'), C46'(H46'), C50'(H50'), C52'(H52'),
 C54'(H54')
6.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,
 H18B,H18C), C9'(H9'A,H9'B,H9'C), C11'(H11D,H11E,H11F), C12'(H12D,H12E,H12F),
 C13'(H13D,H13E,H13F), C14'(H14D,H14E,H14F), C16'(H16D,H16E,H16F), C17'(H17D,
 H17E,H17F), C18'(H18D,H18E,H18F)
;
_shelx_res_checksum              13473
_shelx_hkl_checksum              3672
_olex2_submission_special_instructions 'No special instructions were received'