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_7133160
_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         'C27 H29 N O4 S2'
_chemical_formula_sum            'C27 H29 N O4 S2'
_chemical_formula_weight         495.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-02
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-09-09 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.178(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.24180(10)
_cell_length_b                   19.5215(3)
_cell_length_c                   14.0366(2)
_cell_measurement_reflns_used    5512
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      73.4210
_cell_measurement_theta_min      4.5270
_cell_volume                     2499.98(6)
_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      100.0(6)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_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    -33.00  28.00   0.50    0.50    --    0.00 -82.00 -60.00  122
  2  \w    -33.00  20.00   0.50    0.50    --    0.00 -82.00-150.00  106
  3  \w    -28.00  12.00   0.50    0.50    --    0.00 -82.00  60.00   80
  4  \w    -31.00  -6.00   0.50    0.50    --    0.00 -82.00  30.00   50
  5  \w     71.00  97.00   0.50    0.80    --   95.80 -45.00  60.00   52
  6  \w      6.00 119.00   0.50    0.80    --   95.80 -61.00  30.00  226
  7  \w     79.00 121.00   0.50    0.80    --   95.80  30.00-180.00   84
  8  \w      6.00  67.00   0.50    0.80    --   95.80 -45.00  60.00  122
  9  \w     54.00  98.00   0.50    0.80    --   95.80 -30.00 150.00   88
 10  \w      6.00 127.00   0.50    0.80    --   95.80 -82.00  30.00  242
 11  \w     73.00 134.00   0.50    0.80    --   95.80  61.00-180.00  122
 12  \w     83.00 173.00   0.50    0.80    --   95.80  30.00-120.00  180
;
_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      -0.0159102000
_diffrn_orient_matrix_UB_12      0.0065130000
_diffrn_orient_matrix_UB_13      -0.1105695000
_diffrn_orient_matrix_UB_21      0.0401946000
_diffrn_orient_matrix_UB_22      0.0764894000
_diffrn_orient_matrix_UB_23      0.0105428000
_diffrn_orient_matrix_UB_31      0.1632127000
_diffrn_orient_matrix_UB_32      -0.0183144000
_diffrn_orient_matrix_UB_33      0.0049832000
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13621
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.432
_diffrn_reflns_theta_min         3.912
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55758
_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    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0543P)^2^+1.0073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4124
_reflns_number_total             4968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01851f2.cif
_cod_data_source_block           lsh-87
_cod_depositor_comments
'Adding full bibliography for 7133159--7133161.cif.'
_cod_database_code               7133160
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16),
 C22(H22), C23(H23), C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              16630
_shelx_hkl_checksum              88654
_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 1.742
_oxdiff_exptl_absorpt_empirical_full_min 0.541