Photocatalytic remote C(sp<sup>3</sup>)-H alkylation of long-chain alkenes: A tandem multicomponent approach <i>via</i> radical translocation.
Ghosh, Krishna Gopal; Das, Debabrata; Srinivasu, Vinjamuri; Pal, Koustav; Sureshkumar, Devarajulu; Chemical science 17 (2026) 5888–5898; doi:10.1039/d5sc08683c

data_1576953
_publ_section_title
;
 Photocatalytic remote C(sp<sup>3</sup>)-H alkylation of long-chain
 alkenes: A tandem multicomponent approach <i>via</i> radical
 translocation.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              5888
_journal_page_last               5898
_journal_paper_doi               10.1039/d5sc08683c
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C23 H35 F3 O8'
_chemical_formula_sum            'C23 H35 F3 O8'
_chemical_formula_weight         496.51
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2g0cc7
_audit_creation_date             2023-05-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-05-22 deposited with the CCDC.	2026-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.3234(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.70612(15)
_cell_length_b                   10.77758(19)
_cell_length_c                   26.5637(4)
_cell_measurement_reflns_used    25409
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      68.1040
_cell_measurement_theta_min      3.3600
_cell_volume                     2459.57(7)
_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 (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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_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     15.00 110.00   0.50    0.20    --   41.33  77.00   0.00  190
  2  \w     15.00 110.00   0.50    0.20    --   41.33  77.00 -60.00  190
  3  \w     29.00 110.00   0.50    0.20    --   41.33  31.00 -80.00  162
  4  \w     99.00 164.00   0.50    0.20    --   96.67 117.00-120.00  130
  5  \w     67.00 153.00   0.50    0.20    --   96.67 168.00 -83.00  172
  6  \w    100.00 164.00   0.50    0.20    --   96.67 116.00 132.00  128
  7  \w     99.00 164.00   0.50    0.20    --   96.67 117.00 150.00  130
  8  \w    104.00 170.00   0.50    0.20    --   96.67  95.00  49.00  132
  9  \w     84.00 165.00   0.50    0.20    --   96.67  31.00 -80.00  162
 10  \w     70.00 165.00   0.50    0.20    --   96.67  77.00-150.00  190
 11  \w     73.00 165.00   0.50    0.20    --   96.67  68.00 -60.00  184
 12  \w     73.00 165.00   0.50    0.20    --   96.67  68.00 -30.00  184
 13  \w     70.00 165.00   0.50    0.20    --   96.67  77.00  30.00  190
 14  \w     78.00 163.00   0.50    0.20    --   96.67  50.00  90.00  170
 15  \w     75.00 164.00   0.50    0.20    --   96.67  59.00 120.00  178
 16  \w     75.00 164.00   0.50    0.20    --   96.67  59.00 150.00  178
 17  \w     83.00 164.00   0.50    0.20    --   96.67  33.00  30.00  162
 18  \w     80.00 163.00   0.50    0.20    --   96.67  42.00-150.00  166
 19  \w     29.00  83.00   0.50    0.20    --   96.67 -68.00 -60.00  108
 20  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00-180.00   78
 21  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00-180.00   54
 22  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00-150.00   78
 23  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00-120.00   54
 24  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00 -90.00   54
 25  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00 -60.00   54
 26  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00 120.00   54
 27  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00  90.00   54
 28  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00  60.00   54
 29  \w     29.00  83.00   0.50    0.20    --   96.67 -68.00  30.00  108
 30  \w     24.00 106.00   0.50    0.20    --   96.67 -95.00 -60.00  164
 31  \w     22.00 106.00   0.50    0.20    --   96.67 -96.00-150.00  168
 32  \w     55.00 117.00   0.50    0.20    --   41.33-168.00-101.00  124
 33  \w     18.00  80.00   0.50    0.20    --   41.33-104.00 -90.00  124
 34  \w     44.00 127.00   0.50    0.20    --   96.67-145.00 150.00  166
 35  \w     30.00 110.00   0.50    0.20    --   96.67-116.00  43.00  160
 36  \w    -25.00  62.00   0.50    0.20    --   41.33 -54.00  60.00  174
 37  \w    -27.00  36.00   0.50    0.20    --   41.33 -31.00 119.00  126
 38  \w    -34.00  24.00   0.50    0.20    --   41.33 -11.00 -60.00  116
 39  \w    -75.00  32.00   0.50    0.20    --  -41.33  95.00  49.00  214
 40  \w    -96.00 -19.00   0.50    0.20    --  -41.33 138.00 150.00  154
 41  \w    -84.00 -15.00   0.50    0.20    --  -82.50 116.00 132.00  138
 42  \w    -37.00  27.00   0.50    0.20    --  -41.33  32.00   0.00  128
 43  \w    -36.00  27.00   0.50    0.20    --  -41.33  31.00 -80.00  126
 44  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00-180.00  192
 45  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00-120.00  192
 46  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00   0.00  192
 47  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00-150.00  192
 48  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00  60.00  192
 49  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00  90.00  192
 50  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00 120.00  192
 51  \w   -109.00 -18.00   0.50    0.20    --  -41.33 -65.00 120.00  182
 52  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00 150.00  192
 53  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00  30.00  192
 54  \w   -109.00 -18.00   0.50    0.20    --  -41.33 -65.00   0.00  182
 55  \w   -109.00 -18.00   0.50    0.20    --  -41.33 -65.00 -90.00  182
 56  \w   -108.00 -21.00   0.50    0.20    --  -41.33 -54.00 -60.00  174
 57  \w   -108.00 -24.00   0.50    0.20    --  -41.33 -43.00  30.00  168
 58  \w   -109.00 -28.00   0.50    0.20    --  -41.33 -31.00 119.00  162
 59  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00  90.00  192
 60  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00 150.00  192
 61  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00  60.00  192
 62  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00   0.00  192
 63  \w   -151.00 -69.00   0.50    0.20    --  -82.50 -31.00 119.00  164
 64  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00 -90.00  192
 65  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00-180.00  192
 66  \w   -150.00 -58.00   0.50    0.20    --  -82.50 -68.00-120.00  184
 67  \w   -156.00 -83.00   0.50    0.20    --  -82.50 -95.00 -60.00  146
 68  \w   -150.00 -78.00   0.50    0.20    --  -82.50-116.00  43.00  144
 69  \w   -112.00 -45.00   0.50    0.20    --  -41.33-168.00-101.00  134
 70  \w   -137.00 -45.00   0.50    0.20    --  -82.50-168.00-101.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1654759000
_diffrn_orient_matrix_UB_12      -0.0523838000
_diffrn_orient_matrix_UB_13      0.0019994000
_diffrn_orient_matrix_UB_21      0.0127638000
_diffrn_orient_matrix_UB_22      -0.0194246000
_diffrn_orient_matrix_UB_23      0.0580026000
_diffrn_orient_matrix_UB_31      -0.0679278000
_diffrn_orient_matrix_UB_32      -0.1315297000
_diffrn_orient_matrix_UB_33      -0.0093648000
_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  0.1984
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            41855
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_min         3.372
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.978
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70901
_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            'metallic whiteish colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0013(2)
_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   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0818P)^2^+0.5279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3914
_reflns_number_total             4479
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08683c2.cif
_cod_data_source_block           kgo13201_auto
_cod_database_code               1576953
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O F'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.953
_diffrn_oxdiff_digest_frames
;
0114105bd448dc90fd764d76311a5efc1000038ccc7
;
_diffrn_oxdiff_digest_hkl
;
017bee2237181b8f84cbdf5f31c03709147054
;
_reflns_odcompleteness_completeness 99.91
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C28(H28a,H28b), C7(H7a,H7b), C12(H12a,H12b), C23(H23a,H23b),
 C4(H4a,H4b), C20(H20a,H20b), C15(H15a,H15b)
2.c Idealised Me refined as rotating group:
 C33(H33a,H33b,H33c), C27(H27a,H27b,H27c), C34(H34a,H34b,H34c), C32(H32a,H32b,
 H32c), C21(H21a,H21b,H21c), C16(H16a,H16b,H16c)
;
_shelx_res_checksum              49566
_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 1.951
_oxdiff_exptl_absorpt_empirical_full_min 0.677