In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles.
Chen, Rongxiang; Ogunlana, Abosede Adejoke; Fang, Shangwen; Long, Wenhao; Sun, Hongmei; Bao, Xiaoguang; Wan, Xiaobing; Organic & biomolecular chemistry 16 (2018) 4683–4687; doi:10.1039/c8ob01067f

data_7156272
_publ_section_title
;
 In situ generation of nitrile oxides from copper carbene and tert-butyl
 nitrite: synthesis of fully substituted isoxazoles.
;
_journal_issue                   25
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4683
_journal_page_last               4687
_journal_paper_doi               10.1039/c8ob01067f
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C19 H21 N O5'
_chemical_formula_sum            'C19 H21 N O5'
_chemical_formula_weight         343.37
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-05-03 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                75.6790(10)
_cell_angle_beta                 88.544(2)
_cell_angle_gamma                79.757(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2521(5)
_cell_length_b                   9.8028(5)
_cell_length_c                   9.9294(5)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.24
_cell_volume                     858.51(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.05
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27853
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.18
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.2298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                3506
_reflns_number_total             3915
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob01067f2.cif
_cod_data_source_block           mo_chen2_0m_a
_cod_depositor_comments          'Adding full bibliography for 7156272.cif.'
_cod_database_code               7156272
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C15(H15A,H15B), C17(H17A,H17B), C16(H16A,H16B), C18(H18A,
 H18B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C6(H6), C8(H8), C7(H7)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'