Regio-reversed alkenyl-arylation of ynamides <i>via</i> 1,3-olefin shift.
Verma, Saumya; Sethi, Manoj; Sahoo, Akhila K.; Chemical science  (2025) –; doi:10.1039/d5sc07853a

data_1576299
_publ_section_title
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 Regio-reversed alkenyl-arylation of ynamides <i>via</i> 1,3-olefin shift.
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_journal_name_full               'Chemical science'
_journal_paper_doi               10.1039/d5sc07853a
_journal_year                    2025
_chemical_formula_moiety         'C40 H40 N2 O2 S'
_chemical_formula_sum            'C40 H40 N2 O2 S'
_chemical_formula_weight         612.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-03-21
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2025-03-21 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.001(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.356(2)
_cell_length_b                   9.5997(12)
_cell_length_c                   22.018(3)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      21.82
_cell_measurement_theta_min      2.31
_cell_volume                     3457.1(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      297.0
_diffrn_measured_fraction_theta_full 1.000
_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  0.0938
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            102943
_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         27.559
_diffrn_reflns_theta_min         1.551
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6941
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1233 before and 0.0727 after correction. The Ratio of minimum to maximum transmission is 0.9309. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.179
_refine_diff_density_min         -1.239
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         7985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0942
_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^)+(0.1480P)^2^+2.2530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2678
_refine_ls_wR_factor_ref         0.3072
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4449
_reflns_number_total             7985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07853a2.cif
_cod_data_source_block           aks101_0m_a
_cod_original_cell_volume        3457.1(9)
_cod_database_code               1576299
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) = Uanis(C18) = Uanis(C19)
Uanis(C12) = Uanis(C10) = Uanis(C11) = Uanis(C13)
Uanis(C10) = Uanis(C11)
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C20(H20A,H20B), C12(H12A,H12B), C17(H17A,H17B), C10(H10A,
 H10B), C18(H18A,H18B), C19(H19A,H19B), C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C25(H25), C22(H22), C23(H23), C37(H37), C4(H4), C9(H9), C28(H28),
 C34(H34), C6(H6), C31(H31), C1(H1), C16(H16), C35(H35), C36(H36), C3(H3),
 C29(H29), C30(H30)
3.c Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C39(H39A,H39B,H39C)
;
_shelx_res_checksum              91300
_olex2_submission_special_instructions 'No special instructions were received'