Organo-Catalyzed Regio- and Geometry-Specific Construction of β-Hydroxyl-α-vinyl Carboxylic Esters: Substrate Scope, Mechanistic Insights, and Applications.
Chai, Yonghai; Zhou, JinJin; Wu, Yanbin; Feng, Yingle; Wang, Panru; Chen, Yange; Wang, Xinying; Zhao, Beibei; Zhang, Qi; The Journal of organic chemistry 83 (2018) 10476–10486; doi:10.1021/acs.joc.8b01510

data_4035137
_publ_section_title
;
 Organo-Catalyzed Regio- and Geometry-Specific Construction of
 \b-Hydroxyl-\a-vinyl Carboxylic Esters: Substrate Scope, Mechanistic
 Insights, and Applications.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10476
_journal_page_last               10486
_journal_paper_doi               10.1021/acs.joc.8b01510
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C19 H19 Cl O3'
_chemical_formula_weight         330.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.598(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5703(4)
_cell_length_b                   8.1574(3)
_cell_length_c                   14.7938(5)
_cell_measurement_reflns_used    4759
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.16
_cell_measurement_theta_min      4.95
_cell_volume                     1701.57(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15606
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.493
_diffrn_reflns_theta_max         67.493
_diffrn_reflns_theta_min         3.805
_exptl_absorpt_coefficient_mu    2.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   1.00000
_exptl_transmission_factor_min   0.19397
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.6047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2462
_reflns_number_total             3065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01510_si_002.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035137
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.745
_shelx_estimated_absorpt_t_max   0.788
_shelx_res_checksum              23080
_shelx_hkl_checksum              52235