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_7061618
_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_moiety         'C24 H21 N O4 S'
_chemical_formula_sum            'C24 H21 N O4 S'
_chemical_formula_weight         419.50
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-02-14
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-11-04 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.229(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2335(3)
_cell_length_b                   18.3922(8)
_cell_length_c                   14.6378(6)
_cell_measurement_reflns_used    8812
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.21
_cell_volume                     2148.63(15)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44337
_diffrn_reflns_theta_full        28.2978
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1169 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.9240.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2967
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       TRIANGULAR
_exptl_crystal_F_000             880.9287
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.3261
_refine_diff_density_min         -0.4031
_refine_diff_density_rms         0.0548
_refine_ls_d_res_high            0.7496
_refine_ls_d_res_low             9.1961
_refine_ls_goodness_of_fit_ref   1.0557
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0557
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.0182
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.5719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -7
_reflns_number_gt                3710
_reflns_number_total             5318
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2nj01907h2.cif
_cod_data_source_block           mo_aks_08022021_vs_7_81_1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7061618--7061619.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7061618
_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 Ternary CH refined with fixed occupancy and ADP/Uiso:
 C21J(H21J)
2.b Secondary CH2 refined with riding coordinates:
 C15B(H15a,H15b), C23N(H23a,H23b), C22R(H22a,H22b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6A(H6A), C3E(H3E), C7K(H7K), C17L(H17L), C10O(H10O), C12P(H12P),
 C8Q(H8Q), C24S(H24S), C9T(H9T)
2.d Idealised Me refined as rotating group:
 C1U(H1Ua,H1Ub,H1Uc)
2.e :
 C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'