Palladium-Catalyzed β-Arylation of Silyl Ketene Acetals and Application to the Synthesis of Benzo-Fused δ-Lactones.
Aspin, Sam; López-Suárez, Laura; Larini, Paolo; Goutierre, Anne-Sophie; Jazzar, Rodolphe; Baudoin, Olivier; Organic letters 15 (2013) 5056–5059; doi:10.1021/ol402398s

data_1512377
_publ_section_title
;
 Palladium-Catalyzed \b-Arylation of Silyl Ketene Acetals and Application
 to the Synthesis of Benzo-Fused \d-Lactones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5056
_journal_page_last               5059
_journal_paper_doi               10.1021/ol402398s
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C11 H9 Cl1 O4'
_chemical_formula_sum            'C11 H9 Cl O4'
_chemical_formula_weight         240.64
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 96.940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6739(9)
_cell_length_b                   8.2420(10)
_cell_length_c                   16.537(2)
_cell_measurement_reflns_used    3321
_cell_measurement_temperature    150
_cell_measurement_theta_max      66.8600
_cell_measurement_theta_min      5.3760
_cell_volume                     1038.3(2)
_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    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7189
_diffrn_reflns_theta_full        66.987
_diffrn_reflns_theta_max         67.128
_diffrn_reflns_theta_min         5.389
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.256
_exptl_absorpt_correction_T_max  0.494
_exptl_absorpt_correction_T_min  0.390
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.299
_refine_diff_density_max         0.75
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1809
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0835
_refine_ls_shift/su_max          0.0001809
_refine_ls_shift/su_mean         0.0000183
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.19P)^2^ + 0.52P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2352
_refine_ls_wR_factor_gt          0.2294
_refine_ls_wR_factor_ref         0.2352
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                1656
_reflns_number_total             1818
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.58
_oxford_diffrn_Wilson_scale      0.12
_oxford_refine_ls_r_factor_ref   0.0858
_oxford_refine_ls_scale          3.50(17)
_oxford_reflns_number_all        1809
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            ol402398s_si_002.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C11 H9 Cl1 O4'
_cod_database_code               1512377
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  14,X'S) H   ( 143,X'S) H   ( 142,X'S) H   ( 141,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;