Three-component regioselective carboamidation of 1,3-enynes <i>via</i> rhodium(III)-catalyzed C-H activation.
Kong, Lingheng; Han, Xi; Hu, Panjie; Wang, Fen; Li, Xingwei; Chemical communications (Cambridge, England) 59 (2023) 6690–6693; doi:10.1039/d3cc01666h

data_7131603
_publ_section_title
;
 Three-component regioselective carboamidation of 1,3-enynes <i>via</i>
 rhodium(III)-catalyzed C-H activation.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6690
_journal_page_last               6693
_journal_paper_doi               10.1039/d3cc01666h
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H28 N4 O'
_chemical_formula_sum            'C28 H28 N4 O'
_chemical_formula_weight         436.54
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2023-02-02 deposited with the CCDC.	2023-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.946(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9949(13)
_cell_length_b                   8.8643(11)
_cell_length_c                   14.6922(19)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    211.0
_cell_measurement_theta_max      68.248
_cell_measurement_theta_min      3.162
_cell_volume                     1238.4(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      211.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15593
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.739
_diffrn_reflns_theta_min         3.162
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1218 before and 0.0740 after correction.
The Ratio of minimum to maximum transmission is 0.8450.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 1321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.29(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4310
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0668P)^2^+0.1059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                3412
_reflns_number_total             4310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01666h2.cif
_cod_data_source_block           s_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7131602--7131603.cif.'
_cod_database_code               7131603
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.848
_shelx_estimated_absorpt_t_min   0.764
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4A)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C8(H8), C12(H12), C14(H14), C16(H16), C20(H20), C26(H26), C15(H15),
 C17(H17), C9(H9), C19(H19), C5(H5), C11(H11), C23(H23), C13(H13)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              38518
_shelx_hkl_checksum              69005
_olex2_submission_special_instructions 'No special instructions were received'