Highly Stereocontrolled and Regiocontrolled Syntheses of 2,3,4-Trisubstituted Alkanoates and Lactones
Christopher P. Hencken; Douglas T. Genna; Maxime A. Siegler; Gary H. Posner; Journal of Organic Chemistry 76 (2011) 5149–5155; doi:10.1021/jo200795f

data_4026401
_publ_contact_author_address
;Department of Chemistry
Johns Hopkins University
Baltimore
MD 21218
USA
;
_publ_contact_author_email       ghp@jhu.edu
_publ_contact_author_name        'Gary H. Posner'
_publ_contact_author_phone       '(410) 516-4670'
_publ_section_title
;
 Highly Stereocontrolled and Regiocontrolled Syntheses of
 2,3,4-Trisubstituted Alkanoates and Lactones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5149
_journal_page_last               5155
_journal_paper_doi               10.1021/jo200795f
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C11 H11 Cl O3'
_chemical_formula_sum            'C11 H11 Cl O3'
_chemical_formula_weight         226.65
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.353(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8322(2)
_cell_length_b                   11.2780(3)
_cell_length_c                   11.6378(3)
_cell_measurement_reflns_used    5112
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      1.77
_cell_volume                     1017.08(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 15.9890
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8505
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
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    1.480
_exptl_crystal_description       rod
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0301P)^2^+0.4366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                1690
_reflns_number_total             1995
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo200795f_si_002_3.cif
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4026401