<i>para</i>-Selective dearomatization of phenols by I(i)/I(iii) catalysis-based fluorination.
Stünkel, Timo; Siebold, Kathrin; Okumatsu, Daichi; Murata, Kazuki; Ruyet, Louise; Daniliuc, Constantin G.; Gilmour, Ryan; Chemical science 14 (2023) 13574–13580; doi:10.1039/d3sc05952a

data_1570328
_publ_section_title
;
 <i>para</i>-Selective dearomatization of phenols by I(i)/I(iii)
 catalysis-based fluorination.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              13574
_journal_page_last               13580
_journal_paper_doi               10.1039/d3sc05952a
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H10 F N O6 S'
_chemical_formula_weight         327.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           'APEX4 v2021.4-0'
_audit_update_record
;
2023-08-16 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.4430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.78220(10)
_cell_length_b                   15.6869(3)
_cell_length_c                   6.85770(10)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.6546
_cell_measurement_theta_min      2.8169
_cell_volume                     692.13(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_probe          'single crystal'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9796
_diffrn_reflns_theta_full        66.65
_diffrn_reflns_theta_max         66.65
_diffrn_reflns_theta_min         5.64
_diffrn_source                   'Cu ImS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'micro focus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.497
_exptl_absorpt_correction_T_max  0.77
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.183
_refine_ls_abs_structure_details
;

Flack x determined using 1068 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2343
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0293P)^2^+0.2875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0672
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.929
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                2317
_reflns_number_total             2343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05952a2.cif
_cod_data_source_block           gil10483_6m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1570328--1570331.cif.
;
_cod_database_code               1570328
_shelx_res_checksum              13835