Rhodium-catalyzed asymmetric one-pot transesterification and [2 + 2 + 2] cycloaddition leading to enantioenriched 3,3-disubstituted phthalides.
Tanaka, Ken; Osaka, Takuya; Noguchi, Keiichi; Hirano, Masao; Organic letters 9 (2007) 1307–1310; doi:10.1021/ol070179j

data_1556116
_publ_section_title
;
 Rhodium-catalyzed asymmetric one-pot transesterification and [2 + 2 + 2]
 cycloaddition leading to enantioenriched 3,3-disubstituted phthalides.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1307
_journal_page_last               1310
_journal_paper_doi               10.1021/ol070179j
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H23 N O4 S 0.5(C3 H6 O)'
_chemical_formula_sum            'C24.5 H26 N O4.5 S'
_chemical_formula_weight         438.52
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-12-27
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.637(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.446(2)
_cell_length_b                   5.8028(6)
_cell_length_c                   16.3488(15)
_cell_measurement_reflns_used    20633
_cell_measurement_temperature    193
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      3.7
_cell_volume                     2259.1(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      193
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21125
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         3.71
_exptl_absorpt_coefficient_mu    1.546
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.517
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881 1589 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.012(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3861
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+1.5129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                3672
_reflns_number_total             3861
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070179jsi20070124_024922.cif
_cod_data_source_block           global
_cod_depositor_comments
;
 Corrected the value of the '_refine_diff_density_rms' data item
 by removing an ASCII start of heading (SOH) symbol.

 Antanas Vaitkus,
 2019-12-11
;
_cod_original_formula_sum        'C24.50 H26 N O4.50 S'
_cod_database_code               1556116