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_7251697
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.7130(3)
_cell_length_b                   9.9112(3)
_cell_length_c                   17.8424(4)
_cell_measurement_reflns_used    5189
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.2740
_cell_measurement_theta_min      3.9680
_cell_volume                     2248.16(10)
_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 0.921
_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    -10.00  42.00   1.00    8.55    --   16.70  77.00   0.00   52
  2  \w    -10.00  42.00   1.00    8.55    --   16.70  77.00 120.00   52
  3  \w      0.00  84.00   1.00    8.55    --   16.70  57.00 -90.00   84
  4  \w      0.00  84.00   1.00    8.55    --   16.70  57.00  30.00   84
  5  \w    -10.00  42.00   1.00    8.55    --   16.70  77.00  90.00   52
  6  \w    -15.00  21.00   1.00    8.55    --   16.70 -99.00 -30.00   36
;
_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      0.0474001000
_diffrn_orient_matrix_UB_12      -0.0242004000
_diffrn_orient_matrix_UB_13      -0.0161136000
_diffrn_orient_matrix_UB_21      -0.0124072000
_diffrn_orient_matrix_UB_22      0.0335200000
_diffrn_orient_matrix_UB_23      -0.0339938000
_diffrn_orient_matrix_UB_31      0.0267064000
_diffrn_orient_matrix_UB_32      0.0584296000
_diffrn_orient_matrix_UB_33      0.0128072000
_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  0.0272
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.339
_diffrn_reflns_theta_min         3.465
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.821
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77194
_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    1.838
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0251P)^2^+3.2750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0823
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1939
_reflns_number_total             2840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc05217c2.cif
_cod_data_source_block           1120-a_auto
_cod_database_code               7251697
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.849
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 H11B-C11
 0.95 with sigma of 0.002
 C11-H11A
 0.95 with sigma of 0.002
3.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8), C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C1(H1), C2(H2)
;
_shelx_res_checksum              13021
_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.861