Organocatalytic C(sp<sup>3</sup>)-H Functionalization of 5-Methyl-2,3-dihydrofuran Derivatives with Trifluoropyruvates via a Sequential exo-Tautomerization/Carbonyl-Ene Process.
Shen, Yao-Bin; Li, Shuai-Shuai; Sun, Yun-Ming; Yu, Liping; Hao, Zhi-Hui; Liu, Qing; Xiao, Jian; The Journal of organic chemistry 84 (2019) 2779–2785; doi:10.1021/acs.joc.8b03170

data_4033688
_publ_section_title
;
 Organocatalytic C(sp<sup>3</sup>)-H Functionalization of
 5-Methyl-2,3-dihydrofuran Derivatives with Trifluoropyruvates via a
 Sequential exo-Tautomerization/Carbonyl-Ene Process.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2779
_journal_page_last               2785
_journal_paper_doi               10.1021/acs.joc.8b03170
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C23 H21 F3 O5'
_chemical_formula_weight         434.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                76.105(9)
_cell_angle_beta                 72.394(9)
_cell_angle_gamma                82.857(8)
_cell_formula_units_Z            2
_cell_length_a                   9.1339(9)
_cell_length_b                   10.4866(11)
_cell_length_c                   11.6100(12)
_cell_measurement_reflns_used    1752
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3280
_cell_measurement_theta_min      4.0790
_cell_volume                     1027.33(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6140
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.233
_diffrn_reflns_theta_max         67.233
_diffrn_reflns_theta_min         4.090
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0110(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0354P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2409
_reflns_number_total             3674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03170_si_002.cif
_cod_data_source_block           exp_9639
_cod_database_code               4033688
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.890
_shelx_estimated_absorpt_t_max   0.899
_shelx_res_checksum              30642
_shelx_hkl_checksum              39368