Synthesis of 5-(Fluoroalkyl)isoxazole Building Blocks by Regioselective Reactions of Functionalized Halogenoximes.
Chalyk, Bohdan A.; Hrebeniuk, Kateryna V.; Fil, Yulia V.; Gavrilenko, Konstantin S.; Rozhenko, Alexander B.; Vashchenko, Bohdan V.; Borysov, Oleksandr V.; Biitseva, Angelina V.; Lebed, Pavlo S.; Bakanovych, Iulia; Moroz, Yurii S.; Grygorenko, Oleksandr O.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02264

data_4033658
_publ_section_title
;
 Synthesis of 5-(Fluoroalkyl)isoxazole Building Blocks by Regioselective
 Reactions of Functionalized Halogenoximes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02264
_journal_year                    2019
_chemical_formula_sum            'C11 H15 F3 N2 O3'
_chemical_formula_weight         280.25
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.0(2)
_cell_angle_beta                 90.1(2)
_cell_angle_gamma                90.0(2)
_cell_formula_units_Z            4
_cell_length_a                   5.2476(9)
_cell_length_b                   18.201(2)
_cell_length_c                   14.8426(18)
_cell_measurement_reflns_used    694
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.342
_cell_measurement_theta_min      3.549
_cell_volume                     1417.6(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5232
_diffrn_reflns_point_group_measured_fraction_full 0.633
_diffrn_reflns_point_group_measured_fraction_max 0.633
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.542
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 310 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       0.024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0782
_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^)+(0.1410P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2024
_refine_ls_wR_factor_ref         0.2260
_reflns_Friedel_coverage         0.272
_reflns_Friedel_fraction_full    0.281
_reflns_Friedel_fraction_max     0.281
_reflns_number_gt                2115
_reflns_number_total             3161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02264_si_002.cif
_cod_data_source_block           t269
_cod_database_code               4033658
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              41129
_shelx_hkl_checksum              14939