Highly Regio- and Diastereoselective Synthesis of CF3-Substituted Lactones via Photoredox-Catalyzed Carbolactonization of Alkenoic Acids.
Yasu, Yusuke; Arai, Yusuke; Tomita, Ren; Koike, Takashi; Akita, Munetaka; Organic letters 16 (2014) 780–783; doi:10.1021/ol403500y

data_1513462
_publ_section_title
;
 Highly Regio- and Diastereoselective Synthesis of CF3-Substituted
 Lactones via Photoredox-Catalyzed Carbolactonization of Alkenoic Acids.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              780
_journal_page_last               783
_journal_paper_doi               10.1021/ol403500y
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C14 H15 F3 O2'
_chemical_formula_weight         272.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 109.730(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.664(2)
_cell_length_b                   10.003(2)
_cell_length_c                   14.245(3)
_cell_measurement_temperature    90(2)
_cell_volume                     1296.2(5)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.910
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0759
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7730
_diffrn_reflns_point_group_measured_fraction_full 0.860
_diffrn_reflns_point_group_measured_fraction_max 0.753
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.873
_diffrn_reflns_theta_min         1.519
_exptl_absorpt_coefficient_mu    0.120
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1254 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -1.4(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5127
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0520P)^2^+0.4162P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1238
_reflns_Friedel_coverage         0.568
_reflns_Friedel_fraction_full    0.711
_reflns_Friedel_fraction_max     0.577
_reflns_number_gt                4001
_reflns_number_total             5127
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol403500y_si_003.cif
_cod_data_source_block           2425_0m
_cod_original_cell_volume        1296.3(5)
_cod_database_code               1513462
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2013-2
_shelx_res_checksum              71828
_shelx_hkl_checksum              26989