Catalytic Asymmetric Radical-Mediated Three-Component Piancatelli-Type Rearrangement of Furylalkenes
Xu, Lei; Zhong, Sishi; Yang, Qian; Wei, Jie; Zou, Jiaming; Li, Hongxiang; Cai, Yunfei; ACS Catalysis 11 (2021) 10198–10207; doi:10.1021/acscatal.1c03119

data_4518934
_publ_section_title
;
 Catalytic Asymmetric Radical-Mediated Three-Component Piancatelli-Type
 Rearrangement of Furylalkenes
;
_journal_issue                   16
_journal_name_full               'ACS Catalysis'
_journal_page_first              10198
_journal_page_last               10207
_journal_paper_doi               10.1021/acscatal.1c03119
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H15 Cl F3 N O'
_chemical_formula_sum            'C19 H15 Cl F3 N O'
_chemical_formula_weight         365.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5492(4)
_cell_length_b                   10.6045(5)
_cell_length_c                   15.0677(8)
_cell_measurement_reflns_used    2025
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.9780
_cell_measurement_theta_min      3.8250
_cell_volume                     1685.61(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -11.00  89.00   1.00    4.71    --   18.58  77.00   0.00  100
  2  \w     -4.00  33.00   1.00    4.71    --  -18.81  57.00-120.00   37
  3  \w    -90.00 -35.00   1.00    4.71    --  -18.81-178.00  90.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0588365000
_diffrn_orient_matrix_UB_12      -0.0326846000
_diffrn_orient_matrix_UB_13      0.0000076000
_diffrn_orient_matrix_UB_21      -0.0217885000
_diffrn_orient_matrix_UB_22      -0.0389028000
_diffrn_orient_matrix_UB_23      0.0351000000
_diffrn_orient_matrix_UB_31      -0.0243003000
_diffrn_orient_matrix_UB_32      -0.0437217000
_diffrn_orient_matrix_UB_33      -0.0311674000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6596
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.899
_diffrn_reflns_theta_min         3.317
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 787 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0525
_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^)+(0.0503P)^2^+0.2606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.814
_reflns_number_gt                2700
_reflns_number_total             3826
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03119_si_002.cif
_cod_data_source_block           20210127-caiyf-xl-001
_cod_depositor_comments
'Adding full bibliography for 4518934--4518935.cif.'
_cod_database_code               4518934
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H15 Cl F3 N O'
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C15(H15), C5(H5), C18(H18), C9(H9), C19(H19), C6(H6),
 C13(H13), C12(H12), C11(H11), C10(H10)
;
_shelx_res_checksum              76747
_shelx_hkl_checksum              40280
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.903