The reaction of acyl cyanides with “Huisgen zwitterion”: an interesting rearrangement involving ester group migration between oxygen and nitrogen atoms
Liu, Xu-Guang; Wei, Yin; Shi, Min; Organic & Biomolecular Chemistry 7 (2009) 4708–4714; doi:10.1039/b913196e

data_7150763
_publ_section_title
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 The reaction of acyl cyanides with &#x201C;Huisgen zwitterion&#x201D;:
 an interesting rearrangement involving ester group migration between
 oxygen and nitrogen atoms
;
_journal_issue                   22
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              4708
_journal_page_last               4714
_journal_paper_doi               10.1039/b913196e
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C19 H25 N3 O7'
_chemical_formula_weight         407.42
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                99.071(3)
_cell_angle_beta                 102.604(3)
_cell_angle_gamma                106.451(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5749(13)
_cell_length_b                   12.355(2)
_cell_length_c                   12.896(2)
_cell_measurement_reflns_used    1163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.283
_cell_measurement_theta_min      5.396
_cell_volume                     1098.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1019
_diffrn_reflns_av_sigmaI/netI    0.0998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6074
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7488
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.423
_exptl_crystal_size_min          0.351
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.854
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1559
_reflns_number_gt                1967
_reflns_number_total             4247
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b913196e.txt
_cod_data_source_block           cd29130
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150763