Catalyst-free intramolecular radical cyclization cascades initiated by the direct homolysis of Csp3–Br under visible light
Huang, Panyi; Yan, Zhiyang; Ling, Jiaxin; Li, Peixuan; Wang, Jiayang; Li, Jianjun; Sun, Bin; Jin, Can; Green Chemistry 25 (2023) 3989–3994; doi:10.1039/D3GC00304C

data_7246659
_publ_section_title
;
 Catalyst-free intramolecular radical cyclization cascades initiated by
 the direct homolysis of Csp3--Br under visible light
;
_journal_issue                   10
_journal_name_full               'Green Chemistry'
_journal_page_first              3989
_journal_page_last               3994
_journal_paper_doi               10.1039/D3GC00304C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C20 H14 F5 N O3'
_chemical_formula_sum            'C20 H14 F5 N O3'
_chemical_formula_weight         411.32
_chemical_name_systematic        1
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-16 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.302(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1352(4)
_cell_length_b                   7.89497(16)
_cell_length_c                   14.2824(4)
_cell_measurement_reflns_used    6843
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9210
_cell_measurement_theta_min      2.7390
_cell_volume                     1812.12(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_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    -18.00   8.00   0.50    0.50    --   42.30 -77.00  60.00   52
  2  \w      0.00  66.00   0.50    0.50    --   42.30 -65.00  90.00  132
  3  \w     54.00  80.00   0.50    0.50    --   42.30  65.00 -30.00   52
  4  \w     11.00  37.00   0.50    0.50    --   42.30 -77.00  60.00   52
  5  \w    -16.00  68.00   0.50    0.50    --   42.30 -77.00-180.00  168
  6  \w     57.00 124.00   0.50    0.50    --   42.30  77.00 -90.00  134
  7  \w      2.00  64.00   0.50    0.50    --   42.30 -65.00-150.00  124
  8  \w     92.00 130.00   0.50    0.50    --   42.30  65.00 -30.00   76
  9  \w     39.00  69.00   0.50    0.50    --   42.30 -82.00  60.00   60
 10  \w    -31.00  -6.00   0.50    0.50    --   42.30 -82.00 -30.00   50
 11  \w    -23.00  16.00   0.50    0.50    --   42.30 -82.00-120.00   78
 12  \w    -44.00 -19.00   0.50    0.50    --   42.30 -77.00-180.00   50
 13  \w     45.00  70.00   0.50    0.50    --   42.30 -82.00-120.00   50
 14  \w     27.00  67.00   0.50    0.50    --   42.30 -65.00 -90.00   80
 15  \w    -45.00  -5.00   0.50    0.50    --   42.30 -65.00 -90.00   80
 16  \w    -45.00  26.00   0.50    0.50    --   42.30 -82.00  60.00  142
 17  \w    -43.00 -17.00   0.50    0.50    --   42.30 -65.00  90.00   52
 18  \w    -42.00 -17.00   0.50    0.50    --   42.30 -43.00   0.00   50
 19  \w    -11.00  70.00   0.50    0.50    --   42.30 -43.00   0.00  162
 20  \w     30.00  70.00   0.50    0.50    --   42.30 -82.00 -30.00   80
 21  \w     37.00 124.00   0.50    0.50    --   93.70 -42.00 -60.00  174
 22  \w     44.00  98.00   0.50    0.50    --   93.70 -82.00-120.00  108
 23  \w     64.00 118.00   0.50    0.50    --   93.70 -50.00-150.00  108
 24  \w     76.00 108.00   0.50    0.50    --   93.70 -59.00  90.00   64
 25  \w    126.00 166.00   0.50    0.50    --   93.70  33.00 -30.00   80
 26  \w     27.00  53.00   0.50    0.50    --   93.70 -59.00  90.00   52
 27  \w     61.00 108.00   0.50    0.50    --   93.70  33.00 -30.00   94
 28  \w      4.00  51.00   0.50    0.50    --   93.70 -50.00-150.00   94
 29  \w     77.00 103.00   0.50    0.50    --   93.70 -77.00 -90.00   52
 30  \w     79.00 110.00   0.50    0.50    --   93.70 -82.00-180.00   62
 31  \w     39.00  92.00   0.50    0.50    --   93.70 -82.00 -30.00  106
 32  \w     66.00  92.00   0.50    0.50    --   93.70 -82.00  90.00   52
 33  \w    139.00 165.00   0.50    0.50    --   93.70  82.00-150.00   52
 34  \w    104.00 130.00   0.50    0.50    --   93.70  82.00-150.00   52
 35  \w     60.00  99.00   0.50    0.50    --   93.70 -82.00  60.00   78
 36  \w     47.00 112.00   0.50    0.50    --   93.70 -59.00   0.00  130
 37  \w      4.00  98.00   0.50    0.50    --   93.70 -82.00-150.00  188
 38  \w     53.00 106.00   0.50    0.50    --   93.70 -82.00   0.00  106
 39  \w    138.00 164.00   0.50    0.50    --   93.70 -17.00  60.00   52
 40  \w     71.00 101.00   0.50    0.50    --   93.70 -82.00 -90.00   60
 41  \w    108.00 134.00   0.50    0.50    --   93.70 -17.00  60.00   52
 42  \w     48.00 109.00   0.50    0.50    --   93.70 -82.00 120.00  122
 43  \w      4.00  91.00   0.50    0.50    --   93.70 -17.00  60.00  174
 44  \w      4.00  29.00   0.50    0.50    --   93.70 -17.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0262152000
_diffrn_orient_matrix_UB_12      -0.1097253000
_diffrn_orient_matrix_UB_13      0.0732674000
_diffrn_orient_matrix_UB_21      -0.0479086000
_diffrn_orient_matrix_UB_22      -0.1190642000
_diffrn_orient_matrix_UB_23      -0.0862388000
_diffrn_orient_matrix_UB_31      0.0787850000
_diffrn_orient_matrix_UB_32      -0.1089387000
_diffrn_orient_matrix_UB_33      0.0205028000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13174
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.112
_diffrn_reflns_theta_min         2.750
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
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    1.508
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0016(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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0662
_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^)+(0.1412P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.1987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2582
_reflns_number_total             3278
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc00304c2.cif
_cod_data_source_block           exp_2605_auto
_cod_depositor_comments          'Adding full bibliography for 7246659.cif.'
_cod_original_cell_volume        1812.11(8)
_cod_database_code               7246659
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.921
_diffrn_oxdiff_digest_frames
;
01e7fff6b3130d25e53b9ccbc1e543ae0a000299d14
;
_diffrn_oxdiff_digest_hkl
;
01dc9fa24fc2036fef51f75b0b53be08510612
;
_reflns_odcompleteness_completeness 99.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: F1A(0.5) F2A(0.5) F3A(0.5) F1B(0.5) F2B(0.5) F3B(0.5)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C19(H19)
;
_shelx_res_checksum              92746
_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 8.605
_oxdiff_exptl_absorpt_empirical_full_min 0.290