Regioselective synthesis of isoxazole and 1,2,4-oxadiazole-derived phosphonates via [3 + 2] cycloaddition.
Chalyk, Bohdan A.; Sosedko, Alona S.; Volochnyuk, Dmitriy M.; Tolmachev, Andrey A.; Gavrilenko, Konstantin S.; Liashuk, Oleksandr S.; Grygorenko, Oleksandr O.; Organic & biomolecular chemistry 16 (2018) 9152–9164; doi:10.1039/c8ob02257g

data_7156467
_publ_section_title
;
 Regioselective synthesis of isoxazole and 1,2,4-oxadiazole-derived
 phosphonates via [3 + 2] cycloaddition.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9152
_journal_page_last               9164
_journal_paper_doi               10.1039/c8ob02257g
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C8 H12 N O6 P'
_chemical_formula_weight         249.16
_chemical_name_systematic
'5-(diethoxyphosphoryl)isoxazole-3-carboxylic acid'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-19 deposited with the CCDC.
2018-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                76.209(10)
_cell_angle_beta                 88.157(9)
_cell_angle_gamma                74.094(9)
_cell_formula_units_Z            4
_cell_length_a                   8.2532(8)
_cell_length_b                   11.5789(13)
_cell_length_c                   13.3091(16)
_cell_measurement_reflns_used    12675
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.992
_cell_measurement_theta_min      3.154
_cell_volume                     1187.2(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  Xcalibur"3
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0908
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12471
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_min         3.154
_exptl_absorpt_coefficient_mu    0.244
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             520
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         6841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.879
_refine_ls_R_factor_all          0.1456
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0475P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1483
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3067
_reflns_number_total             6841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02257g2.cif
_cod_data_source_block           tolm315a
_cod_depositor_comments          'Adding full bibliography for 7156467.cif.'
_cod_database_code               7156467
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              11052