Mg(ClO4)2-Promoted [4 + 3] Cycloaddition of Oxindole Derivatives with Conjugated Dienes: Concise Synthesis of Spirocycloheptane Oxindole Derivatives
Liu, Yun; Sun, Zhou; Li, Song; Xiang, Kuirong; Zhang, Yuan; Li, Ying; RSC Adv.  (2016) –; doi:10.1039/C6RA03259A

data_7224525
_publ_section_title
;
 Mg(ClO4)2-Promoted [4 + 3] Cycloaddition of Oxindole Derivatives with
 Conjugated Dienes: Concise Synthesis of Spirocycloheptane Oxindole
 Derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA03259A
_journal_year                    2016
_chemical_formula_moiety         'C19 H17 N O2'
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
2015-10-31 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.426(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.9806(5)
_cell_length_b                   8.6168(2)
_cell_length_c                   20.4475(6)
_cell_measurement_reflns_used    4221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6710
_cell_measurement_theta_min      5.2550
_cell_volume                     2959.55(14)
_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
;
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
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9355
_diffrn_measured_fraction_theta_max 0.9938
_diffrn_measurement_details
;
  1 omega   27.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000    0.0000 26

  2 omega  -22.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000    0.0000 46

  3 omega  -52.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 42

  4 omega   34.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -150.0000 90

  5 omega   39.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -30.0000 64

  6 omega   23.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000   60.0000 93

  7 omega   34.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  150.0000 66

  8 omega   42.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -180.0000 32

  9 omega   46.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   60.0000 26

 10 omega   96.00  166.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000 -180.0000 70

 11 omega   38.00   94.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -90.0000 56

 12 omega   52.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   60.0000 51

 13 omega  104.00  130.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   30.0000 26

 14 omega   50.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -150.0000 43

 15 omega   41.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -180.0000 63

 16 omega   90.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 26

 17 omega   61.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000    0.0000 32

 18 omega   71.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  120.0000 37

 19 omega  131.00  157.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000 -150.0000 26

 20 omega   39.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000    0.0000 52

 21 omega   82.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  150.0000 26

 22 omega  111.00  137.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   12.0000  150.0000 26

 23 omega   69.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -60.0000 26

 24 omega  121.00  147.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -60.0000 26

 25 omega   86.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000 -180.0000 45

 26 omega   71.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 37

 27 omega   45.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -107.0000   67.0000 68

 28 omega  134.00  162.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   30.0000 28

 29 omega   86.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000 -150.0000 26

 30 omega   40.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -91.0000  -30.0000 73

 31 omega   50.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   60.0000 25

 32 omega   97.00  147.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -80.0000   60.1860 50

 33 omega  102.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -30.0000 30

 34 omega   46.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -80.0000   60.1860 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0818971000
_diffrn_orient_matrix_UB_12      -0.0763350000
_diffrn_orient_matrix_UB_13      -0.0006349000
_diffrn_orient_matrix_UB_21      0.0411157000
_diffrn_orient_matrix_UB_22      0.1556192000
_diffrn_orient_matrix_UB_23      0.0203052000
_diffrn_orient_matrix_UB_31      0.0032304000
_diffrn_orient_matrix_UB_32      -0.0436939000
_diffrn_orient_matrix_UB_33      0.0734287000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8182
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.05
_diffrn_reflns_theta_min         5.27
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69320
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.3400
_exptl_crystal_size_mid          0.1200
_exptl_crystal_size_min          0.0800
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0639
_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^)+(0.1264P)^2^+0.8583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.1780
_reflns_number_gt                2526
_reflns_number_total             2808
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra03259a2.cif
_cod_data_source_block           liuy1031
_cod_original_cell_volume        2959.57(14)
_cod_database_code               7224525
_reflns_odcompleteness_completeness 93.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C14(H14), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C)
;