Ethyl 2-Cyano-2-(4-nitrophenylsulfonyloxyimino)acetate-Mediated Lossen Rearrangement: Single-Pot Racemization-Free Synthesis of Hydroxamic Acids and Ureas from Carboxylic Acids.
Thalluri, Kishore; Manne, Srinivasa Rao; Dev, Dharm; Mandal, Bhubaneswar; The Journal of organic chemistry 79 (2014) 3765–3775; doi:10.1021/jo4026429

data_4029298
_publ_section_title
;
 Ethyl 2-Cyano-2-(4-nitrophenylsulfonyloxyimino)acetate-Mediated Lossen
 Rearrangement: Single-Pot Racemization-Free Synthesis of Hydroxamic Acids
 and Ureas from Carboxylic Acids.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3765
_journal_page_last               3775
_journal_paper_doi               10.1021/jo4026429
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C9 H10 N2 O3'
_chemical_formula_weight         194.19
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7212(14)
_cell_length_b                   9.3821(13)
_cell_length_c                   11.148(2)
_cell_measurement_temperature    296(2)
_cell_volume                     912.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 100.00
_diffrn_measured_fraction_theta_max 100.00
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0808
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1699
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(1)
_refine_ls_extinction_method     mixed
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0836
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+2.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2139
_refine_ls_wR_factor_ref         0.2490
_reflns_number_gt                672
_reflns_number_total             977
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4026429_si_002.cif
_cod_data_source_block           kisor
_cod_depositor_comments          'Adding full bibliography for 4029298.cif.'
_cod_original_cell_volume        912.1(3)
_cod_original_sg_symbol_H-M      ' P 21 21 21'
_cod_database_code               4029298