Pd-catalyzed 5-<i>exo-dig</i> cyclization/etherification cascade of <i>N</i>-propargyl arylamines for the synthesis of polysubstituted furans.
Li, Meng-Ru; Zheng, Meng-Yao; Wang, Dong-Chao; Guo, Hai-Ming; Chemical communications (Cambridge, England) 60 (2024) 7721–7724; doi:10.1039/d4cc02255f

data_7133288
_publ_section_title
;
 Pd-catalyzed 5-<i>exo-dig</i> cyclization/etherification cascade of
 <i>N</i>-propargyl arylamines for the synthesis of polysubstituted
 furans.
;
_journal_issue                   60
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7721
_journal_page_last               7724
_journal_paper_doi               10.1039/d4cc02255f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C25 H27 N O5 S'
_chemical_formula_sum            'C25 H27 N O5 S'
_chemical_formula_weight         453.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-18
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-04-04 deposited with the CCDC.	2024-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.428(4)
_cell_angle_beta                 111.448(4)
_cell_angle_gamma                105.959(4)
_cell_formula_units_Z            2
_cell_length_a                   10.6593(4)
_cell_length_b                   11.0723(5)
_cell_length_c                   11.3540(5)
_cell_measurement_reflns_used    5118
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9330
_cell_measurement_theta_min      4.1760
_cell_volume                     1190.40(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_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    -80.00 -31.00   1.00    1.00    --  -35.62 116.00-173.00   49
  2  \w    -79.00 -53.00   1.00    1.00    --  -35.62-165.00 -49.00   26
  3  \w    -25.00   0.00   1.00    1.00    --  -35.62 116.00-173.00   25
  4  \w     25.00  80.00   1.00    1.00    --   35.62-116.00  97.00   55
  5  \w     55.00  80.00   1.00    1.00    --   35.62-165.00 -49.00   25
  6  \w     67.00 108.00   1.00    1.01    --  106.81-116.00  97.00   41
  7  \w     70.00  95.00   1.00    1.01    --  106.81-165.00 -49.00   25
  8  \w     87.00 125.00   1.00    1.01    --  106.81 165.00 -26.00   38
  9  \w    105.00 132.00   1.00    1.01    --  106.81 116.00-173.00   27
 10  \w    -53.00 -19.00   1.00    1.00    --  -35.62 -38.00 -60.00   34
 11  \w    -95.00 -17.00   1.00    1.00    --  -35.62 -38.00-150.00   78
 12  \w    -97.00 -62.00   1.00    1.00    --  -35.62 -38.00 -60.00   35
 13  \w    -93.00 -68.00   1.00    1.00    --  -35.62 165.00 -26.00   25
 14  \w     48.00  73.00   1.00    1.00    --   35.62 -99.00 -90.00   25
 15  \w     65.00 106.00   1.00    1.00    --   35.62 178.00  60.00   41
 16  \w     26.00 102.00   1.00    1.00    --   35.62  57.00 120.00   76
 17  \w     16.00  51.00   1.00    1.00    --   35.62 -57.00 120.00   35
 18  \w      7.00 102.00   1.00    1.00    --   35.62  19.00  60.00   95
 19  \w    129.00 174.00   1.00    1.01    --  106.81  61.00 -30.00   45
 20  \w     89.00 118.00   1.00    1.01    --  106.81  61.00 -30.00   29
 21  \w     51.00  77.00   1.00    1.01    --  106.81-111.00-180.00   26
 22  \w     49.00 123.00   1.00    1.01    --  106.81 -61.00-120.00   74
 23  \w    108.00 155.00   1.00    1.01    --  106.81 111.00  30.00   47
 24  \w     79.00 106.00   1.00    1.01    --  106.81-111.00 -30.00   27
 25  \w     40.00  72.00   1.00    1.01    --  106.81-111.00 -30.00   32
 26  \w     85.00 177.00   1.00    1.01    --  106.81  30.00  30.00   92
 27  \w     68.00 107.00   1.00    1.01    --  106.81 -95.00   0.00   39
 28  \w     87.00 127.00   1.00    1.01    --  106.81  30.00 120.00   40
 29  \w    134.00 161.00   1.00    1.01    --  106.81  30.00 120.00   27
 30  \w     39.00 107.00   1.00    1.01    --  106.81 -95.00-150.00   68
 31  \w     56.00 107.00   1.00    1.01    --  106.81 -95.00 120.00   51
 32  \w     42.00 114.00   1.00    1.01    --  106.81 -45.00 -30.00   72
 33  \w     40.00 110.00   1.00    1.01    --  106.81 -45.00  60.00   70
 34  \w     94.00 177.00   1.00    1.01    --  106.81  30.00 -60.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0594760000
_diffrn_orient_matrix_UB_12      -0.1140637000
_diffrn_orient_matrix_UB_13      0.0611309000
_diffrn_orient_matrix_UB_21      -0.0340839000
_diffrn_orient_matrix_UB_22      0.0879969000
_diffrn_orient_matrix_UB_23      0.0818638000
_diffrn_orient_matrix_UB_31      -0.1475417000
_diffrn_orient_matrix_UB_32      -0.0223053000
_diffrn_orient_matrix_UB_33      -0.1054845000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8739
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.381
_diffrn_reflns_theta_min         4.183
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.500
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
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    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0698P)^2^+0.3192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3960
_reflns_number_total             4526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02255f2.cif
_cod_data_source_block           lmr-20231010_auto
_cod_depositor_comments          'Adding full bibliography for 7133288.cif.'
_cod_database_code               7133288
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
_shelx_estimated_absorpt_t_max   0.662
_shelx_estimated_absorpt_t_min   0.521
_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 riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C7(H7), C31(H31), C4(H4), C5(H5), C27(H27), C6(H6), C30(H30),
 C28(H28)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C32(H32A,H32B,H32C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              8019
_shelx_hkl_checksum              8716
_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 1.255
_oxdiff_exptl_absorpt_empirical_full_min 0.760