Palladium Catalyzed Insertion Reaction of Isocyanides with 3-Arylisoxazol-5(4<i>H</i>)-ones: Synthesis of 4-Aminomethylidene Isoxazolone Derivates.
Zhu, Yi-Ming; Xu, Pei; Wang, Shun-Yi; Ji, Shun-Jun; The Journal of organic chemistry 84 (2019) 11007–11013; doi:10.1021/acs.joc.9b01585

data_4033799
_publ_section_title
;
 Palladium Catalyzed Insertion Reaction of Isocyanides with
 3-Arylisoxazol-5(4<i>H</i>)-ones: Synthesis of 4-Aminomethylidene
 Isoxazolone Derivates.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11007
_journal_page_last               11013
_journal_paper_doi               10.1021/acs.joc.9b01585
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H16 N2 O2'
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.29
_chemical_melting_point          120
_chemical_name_common            zym
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.028(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2250(11)
_cell_length_b                   9.6562(6)
_cell_length_c                   10.7321(9)
_cell_measurement_reflns_used    1703
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9530
_cell_measurement_theta_min      4.3810
_cell_volume                     1287.64(19)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4649
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.511
_diffrn_reflns_theta_min         3.557
_exptl_absorpt_coefficient_mu    0.691
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             522
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0571
_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^)+(0.1074P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1878
_reflns_number_total             2505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01585_si_002.cif
_cod_data_source_block           g170526a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4033799
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 n2(H003), c5(H005), c10(H00D), c14(H00H), c13(H00L), c12(H00M), c11(H00N)
2.b Idealised Me refined as rotating group:
 c3(H00A,H00B,H00C), c1(H00E,H00F,H00G), c2(H00I,H00J,H00K)
;
_shelx_res_checksum              22326
_shelx_hkl_checksum              17910
_olex2_submission_special_instructions 'No special instructions were received'