Catalytic formal cycloadditions between anhydrides and ketones: excellent enantio and diastereocontrol, controllable decarboxylation and the formation of adjacent quaternary stereocentres.
Cornaggia, Claudio; Gundala, Sivaji; Manoni, Francesco; Gopalasetty, Nagaraju; Connon, Stephen J.; Organic & biomolecular chemistry 14 (2016) 3040–3046; doi:10.1039/c6ob00089d

data_7154980
_publ_section_title
;
 Catalytic formal cycloadditions between anhydrides and ketones: excellent
 enantio and diastereocontrol, controllable decarboxylation and the
 formation of adjacent quaternary stereocentres.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3040
_journal_page_last               3046
_journal_paper_doi               10.1039/c6ob00089d
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C17 H14 O6 S'
_chemical_formula_weight         346.35
_chemical_name_systematic
'3 S ,4 R )-3-(Ethoxycarbonyl)-1-oxo-3-(thiophen-2-yl)isochro mane-4-carboxylic acid'
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-01-12 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5357(3)
_cell_length_b                   12.3308(4)
_cell_length_c                   14.9954(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1578.30(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6216
_diffrn_reflns_theta_full        64.87
_diffrn_reflns_theta_max         64.87
_diffrn_reflns_theta_min         4.64
_exptl_absorpt_coefficient_mu    8.837
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             806
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(4)
_refine_ls_extinction_coef       0.0004(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1001P)^2^+1.5854P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                2506
_reflns_number_total             2574
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00089d2.cif
_cod_data_source_block           cu_cc210_0m
_cod_depositor_comments
;
Adding full bibliography for 7154979--7154981.cif.

2018-02-05
Z value changed, the orginal one is absurd and inconsistent with given formula
                 miguel
;
_cod_original_formula_sum        'C17 H14 O6 S '
_cod_original_formula_units_Z    26
_cod_original_formula_weight     61.08
_cod_database_code               7154980