Electrophilic aryl migration of <i>N</i>-benzyl propiolamides to functionalized-acrylamides.
Reddy, Chada Raji; Vinaya, Puthiya Purayil; Ajaykumar, Uprety; Nagendraprasad, Thallamapuram; Chemical communications (Cambridge, England) 61 (2025) 18669–18672; doi:10.1039/d5cc04709a

data_7135105
_publ_section_title
;
 Electrophilic aryl migration of <i>N</i>-benzyl propiolamides to
 functionalized-acrylamides.
;
_journal_issue                   94
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              18669
_journal_page_last               18672
_journal_paper_doi               10.1039/d5cc04709a
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H26 N O2 Se'
_chemical_formula_sum            'C27 H26 N O2 Se'
_chemical_formula_weight         475.45
_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
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-08-15 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.871(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4585(11)
_cell_length_b                   20.644(3)
_cell_length_c                   21.236(3)
_cell_measurement_reflns_used    8652
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.1135
_cell_measurement_theta_min      2.161
_cell_volume                     2387.5(7)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27955
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.755
_exptl_absorpt_coefficient_mu    1.595
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2037 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.047(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         8407
_refine_ls_number_restraints     398
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0617P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5604
_reflns_number_total             8407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04709a2.cif
_cod_data_source_block           KB1098_0m_a
_cod_depositor_comments          'Adding full bibliography for 7135105.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7135105
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.691
_shelx_estimated_absorpt_t_max   0.731
_shelx_res_checksum              83433
_shelx_hkl_checksum              11259