Synthesis of <i>N</i>-(acyloxy)-<i>N</i>-alkynylamides <i>via</i> generation of "C<sub>2</sub>" from hypervalent alkynyliodane and a weak base.
Kagami, Kentaro; Liang, Xueying; Ishibashi, Nanako; Ohrui, Sayaka; Tayu, Masanori; Saito, Nozomi; Chemical communications (Cambridge, England) 59 (2023) 8274–8277; doi:10.1039/d3cc01403g

data_7131800
_publ_section_title
;
 Synthesis of <i>N</i>-(acyloxy)-<i>N</i>-alkynylamides <i>via</i>
 generation of "C<sub>2</sub>" from hypervalent alkynyliodane and a weak
 base.
;
_journal_issue                   53
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8274
_journal_page_last               8277
_journal_paper_doi               10.1039/d3cc01403g
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C20 H15 N O4 S'
_chemical_formula_sum            'C20 H15 N O4 S'
_chemical_formula_weight         365.40
_chemical_melting_point          371(2)
_chemical_name_systematic
N-[(1-naphthoyl)oxy]-N-ethynyl-N-p-toluenesulfonamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2cmzbb
_audit_update_record
;
2022-08-01 deposited with the CCDC.	2023-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.096(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   15.1494(16)
_cell_length_b                   15.0265(16)
_cell_length_c                   7.6701(8)
_cell_measurement_reflns_used    7000
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      2.94
_cell_volume                     1713.4(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1198
_diffrn_reflns_av_unetI/netI     0.0881
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            19514
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         2.973
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.907
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             760.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/cyclohexane'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0773
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1105P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2045
_refine_ls_wR_factor_ref         0.2292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2029
_reflns_number_total             3100
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d3cc01403g2.cif
_cod_data_source_block           03KK038B2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '369-373' was changed to
'371(2)' -- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7131800
_shelx_res_checksum              58244
_shelx_hkl_checksum              27558