Catalyst- and additive-free cascade radical addition/cyclization of N-arylacrylamides with trifluoropyruvates
Tan, Yongbo; Huang, Huawen; Chemical Communications  (2023) –; doi:10.1039/D3CC04542K

data_7132221
_publ_section_title
;
 Catalyst- and additive-free cascade radical addition/cyclization of
 N-arylacrylamides with trifluoropyruvates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04542K
_journal_year                    2023
_chemical_formula_moiety         'C21 H20 F3 N O4'
_chemical_formula_sum            'C21 H20 F3 N O4'
_chemical_formula_weight         407.38
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2023-06-12
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-22 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                103.431(2)
_cell_angle_beta                 92.656(2)
_cell_angle_gamma                90.100(2)
_cell_formula_units_Z            4
_cell_length_a                   10.2852(2)
_cell_length_b                   11.2257(3)
_cell_length_c                   17.4566(4)
_cell_measurement_reflns_used    15304
_cell_measurement_temperature    297.44(10)
_cell_measurement_theta_max      77.1190
_cell_measurement_theta_min      4.0340
_cell_volume                     1958.12(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.44(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.936
_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     96.00 168.00   0.50    0.30    --  108.37  19.00  30.00  144
  2  \w     95.00 166.00   0.50    0.30    --  108.37 125.00  30.00  142
  3  \w    106.00 177.00   0.50    0.30    --  108.37  85.00 -93.00  142
  4  \w    153.00 178.00   0.50    0.30    --  108.37  37.00 -60.00   50
  5  \w     79.00 105.00   0.50    0.30    --  108.37 -85.00 147.00   52
  6  \w     79.00 108.00   0.50    0.30    --  108.37-108.00 110.29   58
  7  \w     70.00 104.00   0.50    0.30    --  108.37-125.00 120.00   68
  8  \w     40.00  69.00   0.50    0.30    --  108.37-108.00 110.29   58
  9  \w     66.00 101.00   0.50    0.30    --  108.37 -99.00  30.00   70
 10  \w     55.00 101.00   0.50    0.30    --  108.37 -99.00   0.00   92
 11  \w     36.00  94.00   0.50    0.30    --  108.37 -99.00 -30.00  116
 12  \w     64.00 111.00   0.50    0.30    --  108.37-125.00 -90.00   94
 13  \w     47.00 108.00   0.50    0.30    --  108.37-125.00-150.00  122
 14  \w     81.00 106.00   0.50    0.30    --  108.37 -99.00-120.00   50
 15  \w     51.00 106.00   0.50    0.30    --  108.37 -99.00 -60.00  110
 16  \w     38.00  63.00   0.50    0.30    --  108.37 -99.00  30.00   50
 17  \w    -21.00  57.00   0.50    0.10    --   48.32 -85.00 147.00  156
 18  \w     81.00 106.00   0.50    0.30    --  108.37 -99.00 150.00   50
 19  \w     40.00  66.00   0.50    0.30    --  108.37 -57.00  90.00   52
 20  \w     40.00  66.00   0.50    0.30    --  108.37 -57.00   0.00   52
 21  \w    -18.00   8.00   0.50    0.10    --   48.32 -19.00-120.00   52
 22  \w     41.00  66.00   0.50    0.30    --  108.37 -57.00 -60.00   50
 23  \w    -28.00  10.00   0.50    0.10    --  -48.32  37.00-150.00   76
 24  \w    -22.00  25.00   0.50    0.10    --  -48.32  19.00-180.00   94
 25  \w    -24.00  17.00   0.50    0.10    --  -48.32  19.00 -90.00   82
 26  \w     -8.00  26.00   0.50    0.10    --  -48.32  19.00 -60.00   68
 27  \w   -103.00 -69.00   0.50    0.30    --  -91.75  77.00-150.00   68
 28  \w    -63.00 -29.00   0.50    0.30    --  -91.75  77.00-150.00   68
 29  \w    -62.00 -19.00   0.50    0.30    --  -91.75  57.00  90.00   86
 30  \w    -66.00 -23.00   0.50    0.30    --  -91.75  57.00 120.00   86
 31  \w    -70.00  23.00   0.50    0.10    --  -48.32  85.00 -93.00  186
 32  \w    -69.00 -36.00   0.50    0.30    --  -91.75  85.00 -93.00   66
 33  \w   -166.00 -81.00   0.50    0.30    --  -91.75 -19.00-150.00  170
 34  \w   -153.00 -79.00   0.50    0.30    --  -91.75 -19.00 -90.00  148
 35  \w   -120.00 -79.00   0.50    0.30    --  -91.75 -19.00 150.00   82
 36  \w   -161.00-136.00   0.50    0.30    --  -91.75 -19.00 150.00   50
 37  \w   -128.00 -92.00   0.50    0.30    --  -91.75 -85.00 147.00   72
 38  \w   -127.00-101.00   0.50    0.30    --  -91.75 -99.00  90.00   52
 39  \w   -154.00-128.00   0.50    0.30    --  -91.75 -99.00  90.00   52
 40  \w   -119.00 -73.00   0.50    0.10    --  -48.32-125.00 -90.00   92
 41  \w   -120.00 -93.00   0.50    0.10    --  -48.32-125.00-150.00   54
 42  \w   -139.00 -88.00   0.50    0.30    --  -91.75 -99.00-150.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0883812000
_diffrn_orient_matrix_UB_12      -0.0631791000
_diffrn_orient_matrix_UB_13      -0.0716306000
_diffrn_orient_matrix_UB_21      0.0167680000
_diffrn_orient_matrix_UB_22      0.1111018000
_diffrn_orient_matrix_UB_23      -0.0366076000
_diffrn_orient_matrix_UB_31      0.1199789000
_diffrn_orient_matrix_UB_32      -0.0597961000
_diffrn_orient_matrix_UB_33      -0.0421940000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24458
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.639
_diffrn_reflns_theta_min         2.605
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0034(3)
_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   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         7798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.1595P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6413
_reflns_number_total             7798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04542k2.cif
_cod_data_source_block           1-dr1
_cod_database_code               7132221
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O F'
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.844
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B), C22(H22A,H22B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C32(H32), C33(H33), C34(H34), C35(H35), C38(H38), C39(H39), C40(H40),
  C41(H41), C42(H42)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C23(H23A,H23B,H23C), C29(H29A,H29B,H29C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O8(H8)
;
_shelx_res_checksum              29849
_shelx_hkl_checksum              15628
_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 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.365