Cationic Co(I) Catalysts for Regiodivergent Hydroalkenylation of 1,6-Enynes: An Uncommon cis-β-C‒H Activation Leads to Z-Selective Coupling of Acrylates
Herbort, James H.; Lalisse, Remy F.; Hadad, Christopher M.; RajanBabu, T. V.; ACS Catalysis  (2021) 9605–9617; doi:10.1021/acscatal.1c02530

data_4518901
_publ_section_title
;
 Cationic Co(I) Catalysts for Regiodivergent Hydroalkenylation of
 1,6-Enynes: An Uncommon cis-\b-C--H Activation Leads to Z-Selective
 Coupling of Acrylates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9605
_journal_page_last               9617
_journal_paper_doi               10.1021/acscatal.1c02530
_journal_year                    2021
_chemical_formula_moiety         'C24 H26 F N O4 S'
_chemical_formula_sum            'C24 H26 F N O4 S'
_chemical_formula_weight         443.52
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-11-09
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.05 svn.r0a1fe1be for OlexSys, GUI svn.r6182)
;
_cell_angle_alpha                109.2290(10)
_cell_angle_beta                 111.1650(10)
_cell_angle_gamma                92.2160(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6410(4)
_cell_length_b                   10.3467(5)
_cell_length_c                   13.3148(5)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.125
_cell_measurement_theta_min      3.412
_cell_volume                     1150.61(9)
_computing_cell_refinement       'SAINT v8.40A (Bruker, 2019)'
_computing_data_collection       'APEX3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.992
_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  0.0223
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37824
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.127
_diffrn_reflns_theta_min         2.946
_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    0.178
_exptl_absorpt_correction_T_max  0.0943
_exptl_absorpt_correction_T_min  0.0693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0432 before and 0.0401 after correction.
The Ratio of minimum to maximum transmission is 0.7349.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       Block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.524
_exptl_crystal_size_mid          0.434
_exptl_crystal_size_min          0.232
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0343P)^2^+0.7028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4665
_reflns_number_total             5047
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02530_si_003.cif
_cod_data_source_block           RBabu_JHH-3191-3
_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/ACS/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               4518901
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.912
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(C4B)
Uanis(C3B) = Uanis(C3)
3. Others
 Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(H12C)=Sof(H12D)=1-FVAR(1)
 Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H12A)=Sof(H12B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C3B(H3B)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C4B(H4BA,H4BB), C12(H12A,H12B), C12(H12C,H12D)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C19(H19), C20(H20),
 C22(H22), C23(H23)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              74750
_shelx_hkl_checksum              15578
_olex2_submission_special_instructions 'No special instructions were received'