Stereoselective Synthesis of Five-Membered Spirooxindoles through Tomita Zipper Cyclization.
Ramachary, D. B.; Venkaiah, Chintalapudi; Krishna, Patoju M.; Organic letters 15 (2013) 4714–4717; doi:10.1021/ol4020305

data_1512313
_publ_section_title
;
 Stereoselective Synthesis of Five-Membered Spirooxindoles through Tomita
 Zipper Cyclization.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4714
_journal_page_last               4717
_journal_paper_doi               10.1021/ol4020305
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C23 H15.59 Cl0.5 N3 O3, 0.5(Cl1)'
_chemical_formula_sum            'C23 H15.59 Cl N3 O3'
_chemical_formula_weight         417.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-08-27
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                82.920(6)
_cell_angle_beta                 86.494(5)
_cell_angle_gamma                82.129(6)
_cell_formula_units_Z            2
_cell_length_a                   7.5903(5)
_cell_length_b                   10.1053(7)
_cell_length_c                   13.3797(9)
_cell_measurement_temperature    293(2)
_cell_volume                     1007.81(12)
_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  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6311
_diffrn_reflns_theta_full        71.50
_diffrn_reflns_theta_max         71.50
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.935
_exptl_absorpt_correction_T_max  0.8010
_exptl_absorpt_correction_T_min  0.5426
_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            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             431
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.960
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.704
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      0.702
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0695
_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^)+(0.1518P)^2^+1.3759P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1873
_refine_ls_wR_factor_ref         0.1960
_reflns_number_gt                3309
_reflns_number_total             3836
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4020305_si_004.cif
_cod_data_source_block           dbr47a
_cod_database_code               1512313
_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. Uiso/Uaniso restraints and constraints
Cl1 \\sim Cl1A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C9 \\sim C9A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(Cl1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C4) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C3) = Uanis(C3A)
Uanis(C2) = Uanis(C2A)
3. Others
 Sof(C3A)=Sof(C2A)=Sof(H2A)=1-FVAR(1)
 Sof(C2)=Sof(H2)=Sof(C3)=FVAR(1)
 Sof(Cl1A)=1-FVAR(2)
 Sof(Cl1)=FVAR(2)
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=1-FVAR(3)
 Sof(C9)=Sof(H9)=FVAR(3)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9A(H9AA,H9AB)
4.b Me refined with riding coordinates:
 C10(H10A,H10B,H10C)
4.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C23(H23), C22(H22), C21(H21), C19(H19), C20(H20), C2(H2), C9(H9),
 C2A(H2A)
;