Polar [3 + 2] cycloaddition of ketones with electrophilically activated carbonyl ylides. Synthesis of spirocyclic dioxolane indolinones
Bentabed-Ababsa, Ghenia; Derdour, Aicha; Roisnel, Thierry; Sáez, Jose A.; Domingo, Luis R.; Mongin, Florence; Organic & Biomolecular Chemistry 6 (2008) 3144–3157; doi:10.1039/b804856h

data_7150945
_publ_section_title
;
 Polar [3 + 2] cycloaddition of ketones with electrophilically
 activated carbonyl ylides. Synthesis of spirocyclic dioxolane
 indolinones
;
_journal_issue                   17
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              3144
_journal_page_last               3157
_journal_paper_doi               10.1039/b804856h
_journal_volume                  6
_journal_year                    2008
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H8 Cl2 N3 O3, C3 H7 O1'
_chemical_formula_sum            'C21 H15 Cl2 N3 O4'
_chemical_formula_weight         444.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.608(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2556(6)
_cell_length_b                   6.9193(3)
_cell_length_c                   22.4721(10)
_cell_measurement_reflns_used    9718
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3
_cell_measurement_wavelength     0.71073
_cell_volume                     2051.26(16)
_computing_cell_refinement       'Bruker SMART, 2006'
_computing_data_collection       'Bruker SMART, 2006'
_computing_data_reduction        'Bruker SAINT, 2006'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            31570
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_correction_T_min  0.786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.036
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0264P)^2^+1.3432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                4579
_reflns_number_total             4692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b804856h.txt
_cod_data_source_block           10b
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7150945