Green and rapid acid-catalyzed ynamide skeletal rearrangement and stereospecific functionalization with anisole derivatives
Mutra, Mohana Reddy; Chandana, T. L.; Wang, Yun-Jou; Wang, Jeh-Jeng; Green Chemistry 25 (2023) 8124–8133; doi:10.1039/D3GC02460A

data_7247337
_publ_section_title
;
 Green and rapid acid-catalyzed ynamide skeletal rearrangement and
 stereospecific functionalization with anisole derivatives
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              8124
_journal_page_last               8133
_journal_paper_doi               10.1039/D3GC02460A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C36 H29 N O3 S'
_chemical_formula_sum            'C36 H29 N O3 S'
_chemical_formula_weight         555.66
_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     dual
_audit_creation_date             2022-07-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-07-08 deposited with the CCDC.	2023-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.505(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7910(4)
_cell_length_b                   18.1795(10)
_cell_length_c                   17.9329(10)
_cell_measurement_reflns_used    6285
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      25.8940
_cell_measurement_theta_min      2.2390
_cell_volume                     2852.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -79.00  38.00   0.50   33.78    --   10.60 -82.00-150.00  234
  2  \w    -15.00 100.00   0.50   33.78    --   10.60  77.00  90.00  230
  3  \w    -20.00 100.00   0.50   33.78    --   10.60  57.00  90.00  240
  4  \w    -79.00  36.00   0.50   33.78    --   10.60 -77.00  60.00  230
  5  \w    -79.00  36.00   0.50   33.78    --   10.60 -77.00 -30.00  230
  6  \w    -70.00  15.00   0.50   33.78    --  -10.90 -82.00 -60.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0037751000
_diffrn_orient_matrix_UB_12      0.0314966000
_diffrn_orient_matrix_UB_13      0.0235992000
_diffrn_orient_matrix_UB_21      -0.0349918000
_diffrn_orient_matrix_UB_22      0.0212964000
_diffrn_orient_matrix_UB_23      -0.0299425000
_diffrn_orient_matrix_UB_31      -0.0729934000
_diffrn_orient_matrix_UB_32      -0.0087039000
_diffrn_orient_matrix_UB_33      0.0113017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29164
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         1.599
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         5003
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0756
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1175P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.2127
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3073
_reflns_number_total             5003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02460a2.cif
_cod_data_source_block           k11107-jjw-a(mr-y-tf)_auto
_cod_depositor_comments          'Adding full bibliography for 7247337.cif.'
_cod_database_code               7247337
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C N S O'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
N1 \\sim O1 \\sim O2 \\sim O3 \\sim S1: within 3.8A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 3.8A
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29), C31(H31), C32(H32), C34(H34), C35(H35)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              78192
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.384
_oxdiff_exptl_absorpt_empirical_full_min 0.455