A 2nd-generation scalable synthesis of the HIV-1 entry inhibitor CJF-III-288 enabled by photoredox catalysis.
Nadraws, Jonathan W.; Pokle, Maithili S.; Smith, 3rd, Amos B; Chemical communications (Cambridge, England) 62 (2026) 2981–2985; doi:10.1039/d5cc06802a

data_7135542
_publ_section_title
;
 A 2nd-generation scalable synthesis of the HIV-1 entry inhibitor
 CJF-III-288 enabled by photoredox catalysis.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2981
_journal_page_last               2985
_journal_paper_doi               10.1039/d5cc06802a
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H50 Br N5 O9 S, C3 H6 O'
_chemical_formula_sum            'C38 H56 Br N5 O10 S'
_chemical_formula_weight         854.84
_chemical_name_systematic        JWN-II-141
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-09-02 deposited with the CCDC.	2026-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.839(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1491(3)
_cell_length_b                   12.2447(3)
_cell_length_c                   14.3618(4)
_cell_measurement_reflns_used    23375
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.2310
_cell_measurement_theta_min      2.3420
_cell_volume                     2098.38(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'Dectris Pilatus3 R 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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     -8.00  85.00   0.50   15.00    --    6.66  37.00 150.00  186
  2  \w     -9.00  59.00   0.50   15.00    --    6.66  57.00 -30.00  136
  3  \w    -25.00  30.00   0.50   15.00    --    6.66 -77.00-180.00  110
  4  \w    -25.00  30.00   0.50   15.00    --    6.66 -77.00  30.00  110
  5  \w     -7.00  75.00   0.50   15.00    --    6.66  37.00  60.00  164
  6  \w    -44.00   7.00   0.50   15.00    --   -6.97 -57.00 120.00  102
  7  \w    -25.00   4.00   0.50   15.00    --   -6.97 -77.00-120.00   58
  8  \w    -31.00  -6.00   0.50   15.00    --   -6.97  77.00-150.00   50
  9  \w    -44.00 -13.00   0.50   15.00    --   -6.97 -57.00  60.00   62
 10  \w    -17.00  56.00   0.50   15.00    --   -6.97   0.00  90.00  146
 11  \w    -85.00 -47.00   0.50   15.00    --   -6.97   0.00  90.00   76
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0130346000
_diffrn_orient_matrix_UB_12      -0.0031922000
_diffrn_orient_matrix_UB_13      -0.0501693000
_diffrn_orient_matrix_UB_21      0.0045106000
_diffrn_orient_matrix_UB_22      0.0576006000
_diffrn_orient_matrix_UB_23      -0.0029021000
_diffrn_orient_matrix_UB_31      0.0578356000
_diffrn_orient_matrix_UB_32      -0.0052284000
_diffrn_orient_matrix_UB_33      -0.0013783000
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43167
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.018
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       plank
_exptl_crystal_F_000             900
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 4057 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         10356
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0239P)^2^+1.3446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                9495
_reflns_number_total             10356
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06802a2.cif
_cod_data_source_block           1490
_cod_database_code               7135542
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.750
_shelx_res_checksum              77814
_shelx_hkl_checksum              48460
_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 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.764