Unlocking reactivity potential of <i>gem</i>-dihaloolefins: access to Halo-functionalized 1,4-naphthoquinones <i>via</i> intramolecular radical oxidative cyclization.
Sharma, Manvi; Thakur, Deepika; Meena, Shivam A.; Nandy, Abhijit; Banerjee, Shibdas; Verma, Akhilesh K.; Chemical communications (Cambridge, England) 62 (2026) 1954–1958; doi:10.1039/d5cc06222e

data_7135510
_publ_section_title
;
 Unlocking reactivity potential of <i>gem</i>-dihaloolefins: access to
 Halo-functionalized 1,4-naphthoquinones <i>via</i> intramolecular radical
 oxidative cyclization.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1954
_journal_page_last               1958
_journal_paper_doi               10.1039/d5cc06222e
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C17 H10 Br F O2'
_chemical_formula_sum            'C17 H10 Br F O2'
_chemical_formula_weight         345.16
_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             2024-11-30
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-17 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.808(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2785(5)
_cell_length_b                   14.3225(6)
_cell_length_c                   9.8230(5)
_cell_measurement_reflns_used    4644
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.2720
_cell_measurement_theta_min      2.0570
_cell_volume                     1391.39(12)
_computing_cell_refinement       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.796
_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  41.00   0.50    1.13    --    5.38  85.00 -35.00   66
  2  \w     -8.00  78.00   0.50    1.13    --    5.38  38.00-150.00  172
  3  \w    -26.00  15.00   0.50    1.13    --    5.38 -85.00-154.00   82
  4  \w    -21.00  13.00   0.50    1.13    --   -5.23 -99.00  30.00   68
  5  \w    -20.00  26.00   0.50    1.13    --   -5.23 -99.00  60.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0714776000
_diffrn_orient_matrix_UB_12      0.0039803000
_diffrn_orient_matrix_UB_13      -0.0201702000
_diffrn_orient_matrix_UB_21      0.0051896000
_diffrn_orient_matrix_UB_22      0.0436780000
_diffrn_orient_matrix_UB_23      0.0351067000
_diffrn_orient_matrix_UB_31      0.0024543000
_diffrn_orient_matrix_UB_32      0.0230243000
_diffrn_orient_matrix_UB_33      -0.0631957000
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.796
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11648
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.051
_diffrn_reflns_theta_min         2.059
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.966
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0296P)^2^+0.9712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0782
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2853
_reflns_number_total             3550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06222e2.cif
_cod_data_source_block           mns-344_auto
_cod_database_code               7135510
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H O Br F'
_chemical_oxdiff_usercomment     06-11-2024
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00D)
;
_shelx_res_checksum              46632
_shelx_hkl_checksum              17531
_olex2_submission_original_sample_id MNS-344
_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 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.752