Geminal homologative fluorination of carbonyl derivatives <i>en route</i> to 1-fluoro-2-haloethyl skeletons.
Miele, Margherita; Castiglione, Davide; Prado-Roller, Alexander; Castoldi, Laura; Pace, Vittorio; Chemical communications (Cambridge, England) 61 (2025) 10792–10795; doi:10.1039/d5cc01542a

data_7134676
_publ_section_title
;
 Geminal homologative fluorination of carbonyl derivatives <i>en route</i>
 to 1-fluoro-2-haloethyl skeletons.
;
_journal_issue                   58
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10792
_journal_page_last               10795
_journal_paper_doi               10.1039/d5cc01542a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C8 H5 Cl4 F'
_chemical_formula_sum            'C8 H5 Cl4 F'
_chemical_formula_weight         261.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-11-25
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.11.02 svn.r19aeb66f for OlexSys, GUI svn.r7078)
;
_audit_update_record
;
2024-12-14 deposited with the CCDC.	2025-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.434(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8894(3)
_cell_length_b                   6.0908(3)
_cell_length_c                   16.5497(9)
_cell_measurement_reflns_used    6263
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.552
_cell_measurement_theta_min      2.533
_cell_volume                     990.58(8)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10830
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_min         2.292
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_T_max  0.5645
_exptl_absorpt_correction_T_min  0.5352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0512 before and 0.0366 after correction.
The Ratio of minimum to maximum transmission is 0.9481.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0233
_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^)+(0.0256P)^2^+0.2204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2415
_reflns_number_total             2927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01542a2.cif
_cod_data_source_block           mo_vipa_mami980_1_p21n
_cod_depositor_comments          'Adding full bibliography for 7134676.cif.'
_cod_database_code               7134676
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.945
_shelx_res_checksum              13693
_shelx_hkl_checksum              18924