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_1576298
_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         'C29 H31 N O4 S2'
_chemical_formula_sum            'C29 H31 N O4 S2'
_chemical_formula_weight         521.67
_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     iterative
_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                100.526(6)
_cell_angle_beta                 106.290(6)
_cell_angle_gamma                104.294(6)
_cell_formula_units_Z            2
_cell_length_a                   9.8038(17)
_cell_length_b                   10.5470(18)
_cell_length_c                   14.691(2)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.82
_cell_measurement_theta_min      2.31
_cell_volume                     1360.1(4)
_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      296.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            52794
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.566
_diffrn_reflns_theta_min         2.070
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6983
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0987 before and 0.0609 after correction. The Ratio of minimum to maximum transmission is 0.9366. 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    1.274
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0902P)^2^+0.3274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5223
_reflns_number_total             6255
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc07853a2.cif
_cod_data_source_block           aks086_0m
_cod_database_code               1576298
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.955
_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.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C9(H9A,H9B), C11(H11A,H11B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C26(H26), C16(H16), C24(H24), C20(H20), C25(H25), C8(H8), C1(H1),
 C19(H19), C18(H18), C17(H17), C5(H5), C2(H2), C4(H4)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              70059
_olex2_submission_special_instructions 'No special instructions were received'