Direct Displacement of Alkoxy Groups of Vinylogous Esters by Grignard Reagents
Anthony J. Brockway; Marcos González-López; James C. Fettinger; Jared T. Shaw; Journal of Organic Chemistry 76 (2011) 3515–3518; doi:10.1021/jo102537n

data_4026230
_publ_section_title
;
 Direct Displacement of Alkoxy Groups of Vinylogous Esters by Grignard
 Reagents
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3515
_journal_page_last               3518
_journal_paper_doi               10.1021/jo102537n
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C21 H18 O4'
_chemical_formula_sum            'C21 H18 O4'
_chemical_formula_weight         334.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.9700(18)
_cell_angle_beta                 110.6151(16)
_cell_angle_gamma                90.8135(18)
_cell_formula_units_Z            4
_cell_length_a                   10.5715(13)
_cell_length_b                   10.8354(13)
_cell_length_c                   15.3212(19)
_cell_measurement_reflns_used    4571
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.76
_cell_volume                     1642.4(3)
_computing_cell_refinement       'SAINT (7.46A) (Bruker, 2006)'
_computing_data_collection       'Apex2 (2.2-0) (Bruker, 2007)'
_computing_data_reduction        'SAINT (7.46A) (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL 5.1, XP (Sheldrick, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7506
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9399
_exptl_absorpt_correction_type   'Twinabs, multi-scan'
_exptl_absorpt_process_details   'TWINABS V2008/3 (Sheldrick, 2008)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       Plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         7506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0722P)^2^+0.2156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1142
_reflns_number_gt                6431
_reflns_number_total             7506
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102537n_si_001.cif
_cod_data_source_block           tw51
_cod_database_code               4026230