Michael Addition-Lactonization of Arylacetyl Phosphonate to β,γ-Unsaturated α-Keto Esters for the Synthesis of Chiral syn-3,4-Dihydropyranones and 5,6-Dihydropyranones.
Zhang, Ming-Liang; Wu, Zhi-Jun; Zhao, Jian-Qiang; Luo, Yuan; Xu, Xiao-Ying; Zhang, Xiao-Mei; Yuan, Wei-Cheng; Organic letters 18 (2016) 5110–5113; doi:10.1021/acs.orglett.6b02558

data_1555817
_publ_section_title
;
 Michael Addition-Lactonization of Arylacetyl Phosphonate to
 \b,\g-Unsaturated \a-Keto Esters for the Synthesis of Chiral
 syn-3,4-Dihydropyranones and 5,6-Dihydropyranones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5110
_journal_page_last               5113
_journal_paper_doi               10.1021/acs.orglett.6b02558
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H15 Br O4'
_chemical_formula_sum            'C19 H15 Br O4'
_chemical_formula_weight         387.22
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8600(10)
_cell_length_b                   10.8272(16)
_cell_length_c                   22.448(3)
_cell_measurement_reflns_used    5812
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.99
_cell_measurement_theta_min      3.11
_cell_volume                     1667.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0501
_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       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17531
_diffrn_reflns_theta_full        29.64
_diffrn_reflns_theta_max         29.64
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    2.485
_exptl_absorpt_correction_T_max  0.8453
_exptl_absorpt_correction_T_min  0.1405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          1.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0190P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0610
_reflns_number_gt                3982
_reflns_number_total             4607
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02558_si_002.cif
_cod_data_source_block           mo_wlx_zml4_0m
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
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_cod_database_code               1555817