Transition metal/photocatalyst-free skeletal editing of indene with iodonium difluorodiazo reagent to access 2-(difluoromethyl)naphthalene
Yuan, Zong-Rui; Sun, Meng-Qi; Chen, Wei-Chen; Zhang, Zhi-Qi; Ma, Jun-An; Zhang, Fa-Guang; Chemical Communications 61 (2025) 8667–8670; doi:10.1039/D5CC01777G

data_7134526
_publ_section_title
;
 Transition metal/photocatalyst-free skeletal editing of indene with
 iodonium difluorodiazo reagent to access 2-(difluoromethyl)naphthalene
;
_journal_issue                   48
_journal_name_full               'Chemical Communications'
_journal_page_first              8667
_journal_page_last               8670
_journal_paper_doi               10.1039/D5CC01777G
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C26 H29 F2 N O2'
_chemical_formula_sum            'C26 H29 F2 N O2'
_chemical_formula_weight         425.50
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2025-02-22
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-02-24 deposited with the CCDC.	2025-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.04360(10)
_cell_length_b                   64.4922(10)
_cell_length_c                   8.45790(10)
_cell_measurement_reflns_used    10675
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.7710
_cell_measurement_theta_min      2.7280
_cell_volume                     4387.53(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.970
_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     17.00  57.00   0.50    0.05    --   36.61  57.00-120.00   80
  2  \w     37.00  62.00   0.50    0.05    --   36.61  57.00-150.00   50
  3  \w     88.00 173.00   0.50    0.08    --  109.42  61.00   0.00  170
  4  \w    123.00 164.00   0.50    0.08    --  109.42  77.00  90.00   82
  5  \w     95.00 136.00   0.50    0.08    --  109.42  65.00 146.00   82
  6  \w    120.00 167.00   0.50    0.08    --  109.42  45.00 -30.00   94
  7  \w     89.00 175.00   0.50    0.08    --  109.42  45.00 -90.00  172
  8  \w    111.00 170.00   0.50    0.08    --  109.42  30.00-120.00  118
  9  \w     31.00  75.00   0.50    0.08    --  109.42 -77.00-120.00   88
 10  \w     31.00  77.00   0.50    0.08    --  109.42 -77.00  30.00   92
 11  \w     31.00  65.00   0.50    0.08    --  109.42 -77.00  60.00   68
 12  \w     44.00  87.00   0.50    0.05    --   36.61-140.00-150.00   86
 13  \w      7.00  55.00   0.50    0.05    --   36.61 -99.00 -90.00   96
 14  \w      8.00  33.00   0.50    0.05    --   36.61 -99.00   0.00   50
 15  \w     46.00  78.00   0.50    0.05    --   36.61 -99.00   0.00   64
 16  \w    -32.00  54.00   0.50    0.05    --   36.61 -65.00  11.00  172
 17  \w    -51.00 -26.00   0.50    0.05    --   36.61 -19.00 120.00   50
 18  \w    -51.00 -16.00   0.50    0.05    --   36.61 -19.00  30.00   70
 19  \w    -51.00 -22.00   0.50    0.05    --   36.61 -19.00 -30.00   58
 20  \w    -48.00 -17.00   0.50    0.05    --   36.61 -19.00 -60.00   62
 21  \w    -47.00 -17.00   0.50    0.05    --   36.61 -19.00-120.00   60
 22  \w    -54.00 -15.00   0.50    0.05    --  -36.61 -57.00 -60.00   78
 23  \w    -53.00 -27.00   0.50    0.05    --  -36.61 -57.00-150.00   52
 24  \w    -56.00 -31.00   0.50    0.05    --  -36.61 -57.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1119803000
_diffrn_orient_matrix_UB_12      0.0038642000
_diffrn_orient_matrix_UB_13      0.1447886000
_diffrn_orient_matrix_UB_21      -0.0876842000
_diffrn_orient_matrix_UB_22      0.0177575000
_diffrn_orient_matrix_UB_23      -0.0888774000
_diffrn_orient_matrix_UB_31      -0.1282481000
_diffrn_orient_matrix_UB_32      -0.0155132000
_diffrn_orient_matrix_UB_33      -0.0657062000
_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  0.0353
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       77
_diffrn_reflns_limit_k_min       -79
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16726
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.800
_diffrn_reflns_theta_min         2.741
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0742
_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^)+(0.0610P)^2^+12.7461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1928
_refine_ls_wR_factor_ref         0.1939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4009
_reflns_number_total             4231
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01777g2.cif
_cod_data_source_block           t31
_cod_depositor_comments
'Adding full bibliography for 7134525--7134526.cif.'
_cod_database_code               7134526
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S F'
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.915
_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:
 C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C10(H10), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              22332
_shelx_hkl_checksum              12280
_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 1.913
_oxdiff_exptl_absorpt_empirical_full_min 0.648