I2/O2-Promoted Domino Reactions of Isatins or 3-Hydroxyindolin-2-one Derivatives with Enaminones
Wen-Juan Hao; Jian-Qiang Wang; Xiao-Ping Xu; Shi-Lei Zhang; Shun-Yi Wang; Shun-Jun Ji; Journal of Organic Chemistry 78 (2013) 12362–12373; doi:10.1021/jo401773j

data_4028837
_publ_contact_author_name
;
;
_publ_section_title
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 I2/O2-Promoted Domino Reactions of Isatins or 3-Hydroxyindolin-2-one
 Derivatives with Enaminones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12362
_journal_page_last               12373
_journal_paper_doi               10.1021/jo401773j
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C23 H18 N2 O2'
_chemical_formula_sum            'C23 H18 N2 O2'
_chemical_formula_weight         354.39
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-03
_audit_creation_method
;
  Olex2 1.2
  (compiled Mar 21 2013 11:16:32, GUI svn.r4446)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.790(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.0418(8)
_cell_length_b                   11.3456(9)
_cell_length_c                   28.3218(19)
_cell_measurement_reflns_used    2534
_cell_measurement_temperature    200.01(10)
_cell_measurement_theta_max      23.9010
_cell_measurement_theta_min      3.3010
_cell_volume                     3540.3(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      200.01(10)
_diffrn_detector_area_resol_mean 10.4692
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_details
;
  1 omega  -43.00  -17.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9253   82.0000  -48.0000 26

  2 omega -102.00  -77.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9253 -178.0000 -120.0000 25

  3 omega  -29.00   23.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.9253  -82.0000 -169.0000 52

  4 omega  -25.00   18.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       12.0816  -99.0000   60.0000 43

  5 omega   49.00   97.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       12.0816  178.0000 -180.0000 48

  6 omega  -61.00   -7.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       12.0816  -57.0000  -30.0000 54
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0253276000
_diffrn_orient_matrix_UB_12      0.0541693000
_diffrn_orient_matrix_UB_13      -0.0070666000
_diffrn_orient_matrix_UB_21      0.0199766000
_diffrn_orient_matrix_UB_22      -0.0275592000
_diffrn_orient_matrix_UB_23      -0.0205695000
_diffrn_orient_matrix_UB_31      -0.0557227000
_diffrn_orient_matrix_UB_32      0.0147108000
_diffrn_orient_matrix_UB_33      -0.0125135000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.1212
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            20509
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.88
_diffrn_source                   'Enhance (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       prism
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         7228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.1456
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1962
_reflns_number_gt                3754
_reflns_number_total             7228
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401773j_si_002.cif
_cod_data_source_block           g130403a
_cod_original_cell_volume        3540.3(5)
_cod_database_code               4028837
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C19(H19), C25(H25), C26(H26), C28(H28), C29(H29), C34(H34), C35(H35), C36(H36),
  C37(H37), C42(H42)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C30(H30A,H30B,
 H30C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C)
;