In situ ortho-lithiation/functionalization of pentafluorosulfanyl arenes
Le, Thanh V.; Daugulis, Olafs; Chemical Communications  (2022) –; doi:10.1039/D1CC06140B

data_7129382
_publ_section_title
;
 &#x000D; In situ ortho-lithiation/functionalization of
 pentafluorosulfanyl arenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06140B
_journal_year                    2022
_chemical_formula_moiety         'C15 H16 F5 N O S Si'
_chemical_formula_sum            'C15 H16 F5 N O S Si'
_chemical_formula_weight         381.44
_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   mixed
_audit_creation_date             2021-06-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-20 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.1670(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9576(3)
_cell_length_b                   15.6343(3)
_cell_length_c                   9.2554(2)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      65.94
_cell_measurement_theta_min      3.74
_cell_volume                     1708.19(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'narrow frame \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12808
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        65.934
_diffrn_reflns_theta_max         65.934
_diffrn_reflns_theta_min         3.744
_exptl_absorpt_coefficient_mu    2.872
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.4203
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0424P)^2^+0.8621P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0789
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2929
_reflns_number_total             2952
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06140b2.cif
_cod_data_source_block           TL33_XW317
_cod_database_code               7129382
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.611
_shelx_estimated_absorpt_t_min   0.317
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C3(H2), C7(H6), C8(H5), C9(H1), C10(H3), C11(H4), C12(H7), C13(H8)
1.b Idealised Me refined as rotating group:
 C14(H11,H10,H9), C15(H14,H13,H12)
;
_shelx_res_checksum              27641
_olex2_submission_special_instructions 'No special instructions were received'