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_7134525
_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         'C15 H10 F5 I N2 O5 S2'
_chemical_formula_sum            'C15 H10 F5 I N2 O5 S2'
_chemical_formula_weight         584.27
_chemical_name_systematic
'(1-diazo-2,2-difluoro-2-(phenylsulfonyl)ethyl)(phenyl)-iodaneyl trifluoromethanesulfonate'
_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             2025-01-13
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-02-03 deposited with the CCDC.	2025-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.1610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9965(4)
_cell_length_b                   9.6084(3)
_cell_length_c                   15.2172(5)
_cell_measurement_reflns_used    8869
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.909
_cell_measurement_theta_min      2.507
_cell_volume                     2046.46(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22518
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.034
_diffrn_reflns_theta_max         25.034
_diffrn_reflns_theta_min         2.507
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.844
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0867 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.8313.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/diethyl ether'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.019
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3592
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0336P)^2^+6.2132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2741
_reflns_number_total             3592
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01777g2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7134525--7134526.cif.'
_cod_database_code               7134525
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.837
_shelx_estimated_absorpt_t_min   0.709
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 O3, S1
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C11(H11), C6(H6), C2(H2), C14(H14), C12(H12), C13(H13), C5(H5),
 C3(H3), C4(H4)
;
_shelx_res_checksum              5474
_shelx_hkl_checksum              52645
_olex2_submission_special_instructions 'No special instructions were received'