Metal-free stereoselective addition of propiolic acids to ynamides: a concise synthetic route to highly substituted enediyne/dienyne-(E)-N,O-acetals
Prasad, Rangu; Kanikarapu, Suresh; Dutta, Shubham; Vangara, Srinivas; Sahoo, Akhila K.; New Journal of Chemistry 46 (2022) 13981–13986; doi:10.1039/D2NJ01907H

data_7061619
_publ_section_title
;
 Metal-free stereoselective addition of propiolic acids to ynamides: a
 concise synthetic route to highly substituted
 enediyne/dienyne-(E)-N,O-acetals
;
_journal_issue                   29
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13981
_journal_page_last               13986
_journal_paper_doi               10.1039/D2NJ01907H
_journal_volume                  46
_journal_year                    2022
_chemical_formula_sum            'C27 H23 N O4 S'
_chemical_formula_weight         457.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-11-04 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.793(3)
_cell_length_b                   15.899(5)
_cell_length_c                   17.594(6)
_cell_measurement_reflns_used    196
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      10.90
_cell_measurement_theta_min      2.56
_cell_volume                     2459.6(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker APEX3'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon III detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26882
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_min         2.315
_diffrn_source                   'micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6806
_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    1.236
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1059 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         6113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.0227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3288
_reflns_number_total             6113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj01907h2.cif
_cod_data_source_block           mo_AKS_18022021_VS_7_82_4_1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7061618--7061619.cif.'
_cod_database_code               7061619
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              50666