Phosphinic acid-promoted addition reaction of isocyanides to (Z)-hydroximoyl chlorides: efficient synthesis of α-(hydroxyimino)amides.
Soeta, Takahiro; Takashita, Suguru; Sakata, Yoko; Ukaji, Yutaka; Organic & biomolecular chemistry 14 (2015) 694–700; doi:10.1039/c5ob02032h

data_7154771
_publ_section_title
;
 Phosphinic acid-promoted addition reaction of isocyanides to
 (Z)-hydroximoyl chlorides: efficient synthesis of
 \a-(hydroxyimino)amides.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              694
_journal_page_last               700
_journal_paper_doi               10.1039/c5ob02032h
_journal_volume                  14
_journal_year                    2015
_chemical_formula_moiety         C12H16N2O2
_chemical_formula_sum            'C12 H16 N2 O2'
_chemical_formula_weight         220.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-09-28 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.939(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.604(2)
_cell_length_b                   10.844(2)
_cell_length_c                   11.111(3)
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_cell_measurement_temperature    93
_cell_measurement_theta_max      25.096
_cell_measurement_theta_min      3.498
_cell_volume                     1254.4(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
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_computing_molecular_graphics    ORTEP-3
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 14.4613
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku Mercury (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
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_diffrn_reflns_Laue_measured_fraction_max 0.983
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_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11158
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_min         3.498
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku/MSC Inc., 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             472
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_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.197
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0987P)^2^+0.1852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1622
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1780
_reflns_number_total             2195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02032h2.cif
_cod_data_source_block           soeta01
_cod_depositor_comments          'Adding full bibliography for 7154771.cif.'
_cod_database_code               7154771
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.976
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_shelx_res_checksum              24259