Radical cascade synthesis of γ-amino acids or γ-lactams via carboxyl-mediated intramolecular C–H amination
Huang, Tao; Liu, Can; Yuan, Pan-Feng; Wang, Tao; Yang, Biao; Ma, Yao; Liu, Qiang; Green Chemistry 26 (2024) 9859–9868; doi:10.1039/D4GC03057E

data_7249223
_publ_section_title
;
 Radical cascade synthesis of \g-amino acids or \g-lactams via
 carboxyl-mediated intramolecular C--H amination
;
_journal_issue                   18
_journal_name_full               'Green Chemistry'
_journal_page_first              9859
_journal_page_last               9868
_journal_paper_doi               10.1039/D4GC03057E
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C13 H12 F3 N O'
_chemical_formula_sum            'C13 H12 F3 N O'
_chemical_formula_weight         255.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-03-01 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.445(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6674(5)
_cell_length_b                   10.0950(4)
_cell_length_c                   11.8549(6)
_cell_measurement_reflns_used    7146
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.7730
_cell_measurement_theta_min      2.7620
_cell_volume                     1152.79(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.810
_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    -12.00  15.00   0.50    0.31    --    4.05 -99.00 -60.00   54
  2  \w    -14.00  36.00   0.50    0.31    --    4.05 -99.00  60.00  100
  3  \w    -27.00  33.00   0.50    0.31    --    4.05 -93.00 172.00  120
  4  \w     48.00  75.00   0.50    0.31    --    4.05  37.00-120.00   54
  5  \w    -22.00  34.00   0.50    0.31    --    4.05  93.00 -74.00  112
  6  \w    -18.00  60.00   0.50    0.31    --   -6.39  37.00-150.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0479115000
_diffrn_orient_matrix_UB_12      -0.0426351000
_diffrn_orient_matrix_UB_13      -0.0088032000
_diffrn_orient_matrix_UB_21      -0.0116856000
_diffrn_orient_matrix_UB_22      -0.0489587000
_diffrn_orient_matrix_UB_23      0.0373404000
_diffrn_orient_matrix_UB_31      -0.0546819000
_diffrn_orient_matrix_UB_32      -0.0268995000
_diffrn_orient_matrix_UB_33      -0.0540020000
_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  0.0245
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.810
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11931
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.707
_diffrn_reflns_theta_min         2.152
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0508P)^2^+0.5237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1118
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2438
_reflns_number_total             2899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc03057e2.cif
_cod_data_source_block           huangt1_0229_auto
_cod_depositor_comments          'Adding full bibliography for 7249223.cif.'
_cod_database_code               7249223
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.92
_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 Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C19(H19A,H19B), C20(H20A,H20B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 N16(H16), C6(H6), C7(H7), C11(H11)
;
_shelx_res_checksum              96613
_shelx_hkl_checksum              73573
_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 1.169
_oxdiff_exptl_absorpt_empirical_full_min 0.803