Facile synthesis of 2-vinylindolines <i>via</i> a phosphine-mediated α-umpolung/Wittig olefination/cyclization cascade process.
Li, Shuhui; Xu, Dan; Yao, Hui; Tan, Mengting; Li, Xiaoxuan; Liu, Mingguo; Wang, Long; Huang, Nianyu; Wang, Nengzhong; Chemical communications (Cambridge, England) 60 (2024) 6773–6776; doi:10.1039/d4cc01851f

data_7133159
_publ_section_title
;
 Facile synthesis of 2-vinylindolines <i>via</i> a phosphine-mediated
 &#x3b1;-umpolung/Wittig olefination/cyclization cascade process.
;
_journal_issue                   53
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6773
_journal_page_last               6776
_journal_paper_doi               10.1039/d4cc01851f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C19 H19 N O4 S'
_chemical_formula_sum            'C19 H19 N O4 S'
_chemical_formula_weight         357.41
_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             2023-05-09
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-08-07 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.4680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.30100(10)
_cell_length_b                   11.06510(10)
_cell_length_c                   18.7113(2)
_cell_measurement_reflns_used    15158
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9050
_cell_measurement_theta_min      4.0340
_cell_volume                     1715.51(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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    -24.00   8.00   0.50    0.50    --    0.00 -82.00 -60.00   64
  2  \w    -70.00 -21.00   0.50    0.50    --    0.00 -38.00 -90.00   98
  3  \w    -88.00 -20.00   0.50    0.50    --    0.00 -57.00 -30.00  136
  4  \w    -27.00  31.00   0.50    0.50    --    0.00 -82.00-150.00  116
  5  \w    -33.00  29.00   0.50    0.50    --    0.00 -82.00  30.00  124
  6  \w     -7.00  22.00   0.50    0.50    --    0.00 -57.00 -30.00   58
  7  \w     21.00 104.00   0.50    0.56    --   95.80 -15.00 -60.00  166
  8  \w    156.00 181.00   0.50    0.56    --   95.80  64.00 -38.58   50
  9  \w     71.00  97.00   0.50    0.56    --   95.80  63.00 -69.18   52
 10  \w    120.00 170.00   0.50    0.56    --   95.80  53.00-118.51  100
 11  \w    128.00 184.00   0.50    0.56    --   95.80  62.00 -82.81  112
 12  \w      6.00 110.00   0.50    0.56    --   95.80 -30.00 -60.00  208
 13  \w     74.00 100.00   0.50    0.56    --   95.80  61.00 -60.00   52
 14  \w     72.00 160.00   0.50    0.56    --   95.80  66.00 -19.94  176
 15  \w     74.00 107.00   0.50    0.56    --   95.80  53.00-118.51   66
 16  \w     71.00 150.00   0.50    0.56    --   95.80  64.00 -38.58  158
 17  \w     77.00 102.00   0.50    0.56    --   95.80  45.00 -30.00   50
 18  \w     81.00 184.00   0.50    0.56    --   95.80  77.00  90.00  206
 19  \w     61.00 118.00   0.50    0.56    --   95.80 -77.00 -60.00  114
 20  \w     72.00  98.00   0.50    0.56    --   95.80  15.00 150.00   52
 21  \w    135.00 161.00   0.50    0.56    --   95.80  15.00 150.00   52
 22  \w     72.00  98.00   0.50    0.56    --   95.80  62.00 -82.81   52
 23  \w     89.00 143.00   0.50    0.56    --   95.80  61.00 120.00  108
 24  \w    122.00 185.00   0.50    0.56    --   95.80  63.00 -69.18  126
 25  \w     92.00 118.00   0.50    0.56    --   95.80  82.00  60.00   52
 26  \w    129.00 179.00   0.50    0.56    --   95.80  82.00  60.00  100
 27  \w     81.00 110.00   0.50    0.56    --   95.80  40.00 -70.72   58
 28  \w     76.00 105.00   0.50    0.56    --   95.80  45.00 -90.00   58
 29  \w    115.00 160.00   0.50    0.56    --   95.80  45.00 -90.00   90
 30  \w     76.00 102.00   0.50    0.56    --   95.80  52.00 -61.38   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB 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      -0.1452875000
_diffrn_orient_matrix_UB_12      0.0487743000
_diffrn_orient_matrix_UB_13      -0.0463289000
_diffrn_orient_matrix_UB_21      -0.1155667000
_diffrn_orient_matrix_UB_22      -0.0643879000
_diffrn_orient_matrix_UB_23      0.0488166000
_diffrn_orient_matrix_UB_31      -0.0031468000
_diffrn_orient_matrix_UB_32      0.1135324000
_diffrn_orient_matrix_UB_33      0.0477825000
_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  0.0211
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18184
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.395
_diffrn_reflns_theta_min         4.645
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.884
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0071(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+0.6821P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0772
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3401
_reflns_number_total             3454
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01851f2.cif
_cod_data_source_block           lsh-43
_cod_depositor_comments
'Adding full bibliography for 7133159--7133161.cif.'
_cod_database_code               7133159
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C76 H68 N4 O16 S4 '
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              73790
_shelx_hkl_checksum              78550
_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 2.518
_oxdiff_exptl_absorpt_empirical_full_min 0.827