Visible light-mediated stereoselective haloalkylation of bicyclic alkenes
Tang, Yan; Ponnam, Devendar; Ma, Zhifeng; Tao, Xiong; Sun, Long; Yang, Hekun; Chen, Jingchao; Fan, Baomin; Green Chemistry 28 (2026) 2422–2428; doi:10.1039/D5GC05217C

data_7251698
_publ_section_title
;
 Visible light-mediated stereoselective haloalkylation of bicyclic alkenes
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              2422
_journal_page_last               2428
_journal_paper_doi               10.1039/D5GC05217C
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C12 H10 I N O'
_chemical_formula_sum            'C12 H10 I N O'
_chemical_formula_weight         311.11
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-21
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-04-11 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.071(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9738(8)
_cell_length_b                   8.8365(4)
_cell_length_c                   9.5185(5)
_cell_measurement_reflns_used    4509
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.3760
_cell_measurement_theta_min      4.3370
_cell_volume                     1153.47(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.887
_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    -88.00 -39.00   1.00    2.57    --  -15.92-178.00   0.00   49
  2  \w    -45.00  55.00   1.00    2.57    --  -15.92  19.00  60.00  100
  3  \w    -45.00  55.00   1.00    2.57    --  -15.92  19.00 -30.00  100
  4  \w    -50.00  30.00   1.00    2.57    --   16.85 -57.00-180.00   80
  5  \w    -10.00  42.00   1.00    2.57    --   16.85  77.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0477129000
_diffrn_orient_matrix_UB_12      0.0165421000
_diffrn_orient_matrix_UB_13      0.0377457000
_diffrn_orient_matrix_UB_21      -0.0192513000
_diffrn_orient_matrix_UB_22      0.0545328000
_diffrn_orient_matrix_UB_23      0.0416307000
_diffrn_orient_matrix_UB_31      -0.0048435000
_diffrn_orient_matrix_UB_32      -0.0566312000
_diffrn_orient_matrix_UB_33      0.0510556000
_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  0.0395
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9557
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.304
_diffrn_reflns_theta_min         3.322
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (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    1.792
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.376
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0351P)^2^+0.2292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2282
_reflns_number_total             2795
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc05217c2.cif
_cod_data_source_block           1120-b_auto
_cod_database_code               7251698
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.875
_shelx_estimated_absorpt_t_min   0.831
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C003(H003), C004(H004), C009(H009), C00B(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00D), C00D(H00E), C00E(H00F), C00F(H00G)
;
_shelx_res_checksum              61566
_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 2.238
_oxdiff_exptl_absorpt_empirical_full_min 0.582