Construction of a CF<sub>3</sub>-Containing Benzofurofuranone Skeleton from Coumarins via Reductive Coupling and Acid-Mediated Ring Contraction.
Zhang, Tianyuan; Shimizu, Yuhei; Fukaya, Shuhei; Sawa, Tomofumi; Maekawa, Hirofumi; The Journal of organic chemistry 84 (2019) 12165–12171; doi:10.1021/acs.joc.9b01439

data_4034448
_publ_section_title
;
 Construction of a CF<sub>3</sub>-Containing Benzofurofuranone Skeleton
 from Coumarins via Reductive Coupling and Acid-Mediated Ring Contraction.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12165
_journal_page_last               12171
_journal_paper_doi               10.1021/acs.joc.9b01439
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C12 H9 F3 O3 '
_chemical_formula_sum            'C12 H9 F3 O3'
_chemical_formula_weight         258.20
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 100.222(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   12.4419(3)
_cell_length_b                   5.90535(12)
_cell_length_c                   15.1818(11)
_cell_measurement_reflns_used    8872
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.1
_cell_measurement_theta_min      3.0
_cell_volume                     1097.76(9)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      93.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12118
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_exptl_absorpt_coefficient_mu    1.274
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528.00
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2005
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0722P)^2^+0.1735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                1569
_reflns_number_total             2005
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo9b01439_si_002.cif
_cod_data_source_block           '_sc0602'
_cod_original_cell_volume        1097.76(8)
_cod_original_formula_sum        'C12 H9 F3 O3 '
_cod_database_code               4034448