Diyne-steered switchable regioselectivity in cobalt(II)-catalysed C(sp<sup>2</sup>)-H activation of amides with unsymmetrical 1,3-diynes.
Dhillon, Prakriti; Anaspure, Prasad; Wiklander, Jesper G.; Kathiravan, Subban; Nicholls, Ian A.; Organic & biomolecular chemistry 21 (2023) 1942–1951; doi:10.1039/d2ob02193e

data_7159157
_publ_section_title
;
 Diyne-steered switchable regioselectivity in cobalt(II)-catalysed
 C(sp<sup>2</sup>)-H activation of amides with unsymmetrical 1,3-diynes.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1942
_journal_page_last               1951
_journal_paper_doi               10.1039/d2ob02193e
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C29 H22 N2 O3'
_chemical_formula_weight         446.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-11-02 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.7888(12)
_cell_length_b                   10.0222(4)
_cell_length_c                   12.1293(8)
_cell_measurement_reflns_used    2190
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.17
_cell_measurement_theta_min      2.74
_cell_volume                     2284.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8565
_diffrn_reflns_point_group_measured_fraction_full 0.819
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.168
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       Square
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
; 
 Flack x determined using 922 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.1(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0803P)^2^+0.6130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1438
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_full    0.619
_reflns_Friedel_fraction_max     0.619
_reflns_number_gt                2636
_reflns_number_total             3300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02193e2.cif
_cod_data_source_block           ch5
_cod_depositor_comments
'Adding full bibliography for 7159156--7159161.cif.'
_cod_database_code               7159157
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              54270