Combined experimental and theoretical studies of regio- and stereoselectivity in reactions of β-isoxazolyl- and β-imidazolyl enamines with nitrile oxides
Efimov, Ilya V.; Shafikov, Marsel Z.; Beliaev, Nikolai A.; Volkova, Natalia N.; Beryozkina, Tetyana V.; Dehaen, Wim; Fan, Zhijin; Grishko, Viktoria V.; Lubec, Gert; Slepukhin, Pavel A.; Bakulev, Vasiliy A.; Beilstein Journal of Organic Chemistry 12 (2016) 2390–; doi:10.3762/bjoc.12.233

data_4032064
_publ_section_title
;
 Combined experimental and theoretical studies of regio- and
 stereoselectivity in reactions of \b-isoxazolyl- and \b-imidazolyl
 enamines with nitrile oxides
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              2390
_journal_paper_doi               10.3762/bjoc.12.233
_journal_volume                  12
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H10 N4 O3'
_chemical_formula_sum            'C13 H10 N4 O3'
_chemical_formula_weight         270.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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_date             2016-04-07
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5200(9)
_cell_length_b                   10.4602(5)
_cell_length_c                   17.7675(8)
_cell_measurement_reflns_used    1546
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      30.4020
_cell_measurement_theta_min      2.3310
_cell_volume                     1211.75(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.8106
_diffrn_measurement_details
;
  1 omega  -90.00  -63.00   1.0000   17.0400
omega____ theta____ kappa____ phi______ frames
    -      -20.7924 -178.0000  -60.0000 27

  2 omega  -40.00   86.00   1.0000   17.0400
omega____ theta____ kappa____ phi______ frames
    -       23.2924    0.0000  120.0000 126
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0054641000
_diffrn_orient_matrix_UB_12      0.0257887000
_diffrn_orient_matrix_UB_13      -0.0368415000
_diffrn_orient_matrix_UB_21      -0.1015460000
_diffrn_orient_matrix_UB_22      0.0211825000
_diffrn_orient_matrix_UB_23      0.0071514000
_diffrn_orient_matrix_UB_31      0.0388723000
_diffrn_orient_matrix_UB_32      0.0590439000
_diffrn_orient_matrix_UB_33      0.0135414000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4288
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.1(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0690P)^2^+0.0330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                2489
_reflns_number_total             3018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-12-233-S3.cif
_cod_data_source_block           exp_907
_cod_depositor_comments
;

2020-08-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1211.76(18)
_cod_original_formula_moiety     '0.8(C13 H10 N4 O3)'
_cod_original_formula_sum        'C10.40 H8 N3.20 O2.40'
_cod_original_formula_units_Z    5
_cod_original_formula_weight     216.20
_cod_database_code               4032064
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22