Monofluorinated 5-membered rings via fluoromethylene transfer: synthesis of monofluorinated isoxazoline N-oxides.
Sperga, Arturs; Kazia, Armands; Veliks, Janis; Organic & biomolecular chemistry 19 (2021) 2688–2691; doi:10.1039/d1ob00270h

data_7157901
_publ_section_title
;
 Monofluorinated 5-membered rings via fluoromethylene transfer: synthesis
 of monofluorinated isoxazoline N-oxides.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2688
_journal_page_last               2691
_journal_paper_doi               10.1039/d1ob00270h
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H14 F N O5'
_chemical_formula_sum            'C13 H14 F N O5'
_chemical_formula_weight         283.258
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-04-08
_audit_update_record
;
2021-01-20 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.40072(18)
_cell_length_b                   9.1371(3)
_cell_length_c                   18.7024(6)
_cell_measurement_reflns_used    2203
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.0
_cell_measurement_theta_min      0.9
_cell_volume                     1264.68(7)
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_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  0.0687
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.9985
_diffrn_reflns_Laue_measured_fraction_max 0.9793
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10385
_diffrn_reflns_point_group_measured_fraction_full 0.9956
_diffrn_reflns_point_group_measured_fraction_max 0.9642
_diffrn_reflns_theta_full        79.0
_diffrn_reflns_theta_max         79.0
_diffrn_reflns_theta_min         4.73
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.065
_exptl_absorpt_correction_T_max  0.92362
_exptl_absorpt_correction_T_min  0.88016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       'Block '
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(19)
_refine_ls_extinction_coef       0.0032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0076P)^2^+0.6861P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0825
_reflns_d_resolution_high        0.7853
_reflns_Friedel_coverage         0.943
_reflns_number_gt                2536
_reflns_number_total             2629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob00270h2.cif
_cod_data_source_block           cis3i
_cod_depositor_comments
'Adding full bibliography for 7157901--7157902.cif.'
_cod_original_cell_volume        1264.67(7)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7157901
_shelx_title                     ' AS639II in P212121 #19'
_shelx_refln_list_code           4
_shelx_f_calc_maximum            96.77
_shelx_f_squared_multiplier      1.000