PPh<sub>3</sub> Mediated Reductive Annulation Reaction between Isatins and Electron Deficient Dienes to Construct Spirooxindole Compounds.
Zhang, Lei; Lu, Hong; Xu, Guo-Qiang; Wang, Zhu-Yin; Xu, Peng-Fei; The Journal of organic chemistry 82 (2017) 5782–5789; doi:10.1021/acs.joc.7b00595

data_4037492
_publ_section_title
;
 PPh<sub>3</sub> Mediated Reductive Annulation Reaction between Isatins
 and Electron Deficient Dienes to Construct Spirooxindole Compounds.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5782
_journal_page_last               5789
_journal_paper_doi               10.1021/acs.joc.7b00595
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C30 H23 N3 O5 S'
_chemical_formula_sum            'C30 H23 N3 O5 S'
_chemical_formula_weight         537.57
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.452(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5227(5)
_cell_length_b                   13.8588(4)
_cell_length_c                   15.9556(6)
_cell_measurement_reflns_used    1758
_cell_measurement_temperature    292.78(10)
_cell_measurement_theta_max      22.1220
_cell_measurement_theta_min      3.7310
_cell_volume                     2713.96(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.78(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -18.00   15.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   60.0000 22

  2 omega  -44.00   28.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000  -90.0000 48

  3 omega  -52.00   62.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000  -30.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0510806000
_diffrn_orient_matrix_UB_12      -0.0127406000
_diffrn_orient_matrix_UB_13      -0.0255348000
_diffrn_orient_matrix_UB_21      0.0264396000
_diffrn_orient_matrix_UB_22      -0.0145583000
_diffrn_orient_matrix_UB_23      -0.0333460000
_diffrn_orient_matrix_UB_31      0.0056289000
_diffrn_orient_matrix_UB_32      -0.0473758000
_diffrn_orient_matrix_UB_33      0.0171286000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10470
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1120
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0092(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+0.0616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1636
_reflns_number_gt                3008
_reflns_number_total             5334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00595_si_002.cif
_cod_data_source_block           zhanglei0319
_cod_original_cell_volume        2713.96(16)
_cod_database_code               4037492
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C25(H25), C26(H26), C28(H28), C29(H29)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
;
_olex2_date_sample_data_collection 2015-03-19
_olex2_submission_special_instructions 'No special instructions were received'