Stereoselective synthesis of spirocyclic oxindoles via Prins cyclizations.
Castaldi, M. Paola; Troast, Dawn M.; Porco, Jr, John A; Organic letters 11 (2009) 3362–3365; doi:10.1021/ol901201k

data_1504028
_publ_section_title
;
 Stereoselective synthesis of spirocyclic oxindoles via Prins
 cyclizations.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3362
_journal_page_last               3365
_journal_paper_doi               10.1021/ol901201k
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H23 N O3'
_chemical_formula_sum            'C22 H23 N O3'
_chemical_formula_weight         349.41
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.499(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3610(4)
_cell_length_b                   8.6154(3)
_cell_length_c                   12.8252(5)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.38
_cell_measurement_theta_min      2.36
_cell_volume                     915.94(7)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24000
_diffrn_reflns_theta_full        32.57
_diffrn_reflns_theta_max         32.57
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9514
_exptl_absorpt_correction_T_min  0.9514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.60
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.0711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                3189
_reflns_number_total             3465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901201k_si_002.cif
_cod_data_source_block           porco105
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        915.94(6)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1504028