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_7133161
_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         'C20 H21 N O5 S'
_chemical_formula_sum            'C20 H21 N O5 S'
_chemical_formula_weight         387.44
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-06
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-01-12 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                92.274(6)
_cell_angle_beta                 107.728(8)
_cell_angle_gamma                106.033(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0093(9)
_cell_length_b                   9.9303(10)
_cell_length_c                   13.0524(6)
_cell_measurement_reflns_used    3513
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      73.5200
_cell_measurement_theta_min      3.5840
_cell_volume                     941.63(17)
_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      99.97(15)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.921
_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    -14.00  12.00   0.50    0.50    --    0.00 -82.00  30.00   52
  2  \w    -45.00   3.00   0.50    0.50    --    0.00 -77.00  60.00   96
  3  \w    -33.00  26.00   0.50    0.50    --    0.00 -82.00 -60.00  118
  4  \w    -29.00  15.00   0.50    0.50    --    0.00 -82.00-180.00   88
  5  \w    -27.00  21.00   0.50    0.50    --    0.00 -82.00 120.00   96
  6  \w     -6.00  19.00   0.50    0.50    --    0.00 -82.00-120.00   50
  7  \w      6.00  32.00   0.50    0.50    --   95.80 -82.00-150.00   52
  8  \w     14.00 112.00   0.50    0.50    --   95.80 -30.00-180.00  196
  9  \w     34.00  70.00   0.50    0.50    --   95.80 -77.00-120.00   72
 10  \w      7.00  93.00   0.50    0.50    --   95.80 -61.00 -30.00  172
 11  \w     14.00 107.00   0.50    0.50    --   95.80 -61.00  60.00  186
 12  \w     53.00 117.00   0.50    0.50    --   95.80 -82.00-180.00  128
 13  \w      8.00 106.00   0.50    0.50    --   95.80 -30.00  90.00  196
 14  \w     45.00  75.00   0.50    0.50    --   95.80 -82.00-150.00   60
 15  \w      9.00  34.00   0.50    0.50    --   95.80 -82.00-180.00   50
 16  \w     79.00 173.00   0.50    0.50    --   95.80  15.00 -60.00  188
 17  \w     88.00 118.00   0.50    0.50    --   95.80 -82.00-150.00   60
 18  \w     28.00 123.00   0.50    0.50    --   95.80 -82.00 -30.00  190
 19  \w     24.00 118.00   0.50    0.50    --   95.80 -82.00  60.00  188
 20  \w     93.00 118.00   0.50    0.50    --   95.80  82.00-180.00   50
 21  \w     97.00 122.00   0.50    0.50    --   95.80 -82.00-120.00   50
 22  \w    110.00 184.00   0.50    0.50    --   95.80   0.00  30.00  148
;
_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      0.1212996000
_diffrn_orient_matrix_UB_12      0.1393241000
_diffrn_orient_matrix_UB_13      -0.0204071000
_diffrn_orient_matrix_UB_21      0.0544561000
_diffrn_orient_matrix_UB_22      0.0603984000
_diffrn_orient_matrix_UB_23      0.1201411000
_diffrn_orient_matrix_UB_31      0.1649758000
_diffrn_orient_matrix_UB_32      -0.0590025000
_diffrn_orient_matrix_UB_33      0.0281083000
_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  0.0590
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7837
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.073
_diffrn_reflns_theta_min         3.588
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68900
_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    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.017
_refine_diff_density_min         -1.269
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3580
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0793
_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^)+(0.1534P)^2^+0.7797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2277
_refine_ls_wR_factor_ref         0.2536
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2948
_reflns_number_total             3580
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01851f2.cif
_cod_data_source_block           lsh-130
_cod_depositor_comments
'Adding full bibliography for 7133159--7133161.cif.'
_cod_original_cell_volume        941.63(16)
_cod_database_code               7133161
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N  S'
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              53189
_shelx_hkl_checksum              74949
_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 1.986
_oxdiff_exptl_absorpt_empirical_full_min 0.617