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_7159160
_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_absolute_configuration unk
_chemical_formula_moiety         'C28 H20 N2 O2'
_chemical_formula_sum            'C28 H20 N2 O2'
_chemical_formula_weight         416.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 99.423(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0317(4)
_cell_length_b                   18.8318(12)
_cell_length_c                   8.3435(6)
_cell_measurement_reflns_used    4230
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.14
_cell_measurement_theta_min      2.47
_cell_volume                     1089.93(12)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16022
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.071
_diffrn_reflns_theta_min         2.163
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  07455
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(8)
_refine_ls_extinction_coef       0.038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4777
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0767P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1502
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2644
_reflns_number_total             4777
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02193e2.cif
_cod_data_source_block           S2
_cod_depositor_comments
'Adding full bibliography for 7159156--7159161.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159160
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              9610