Reactions of Nitroso Hetero-Diels-Alder Cycloadducts with Azides: Stereoselective Formation of Triazolines and Aziridines
Brian S. Bodnar; Marvin J. Miller; Journal of Organic Chemistry 72 (2007) 3929–3932; doi:10.1021/jo0701987

data_4022912
_publ_section_title
;
 Reactions of Nitroso Hetero-Diels-Alder Cycloadducts with
 Azides: Stereoselective Formation of Triazolines and Aziridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3929
_journal_page_last               3932
_journal_paper_doi               10.1021/jo0701987
_journal_volume                  72
_journal_year                    2007
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C17 H22 N4 O3'
_chemical_formula_sum            'C17 H22 N4 O3'
_chemical_formula_weight         330.39
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                108.048(2)
_cell_angle_beta                 102.326(2)
_cell_angle_gamma                90.219(2)
_cell_formula_units_Z            2
_cell_length_a                   5.6782(2)
_cell_length_b                   12.3245(4)
_cell_length_c                   12.3822(4)
_cell_measurement_reflns_used    6494
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.02
_cell_measurement_theta_min      2.86
_cell_volume                     802.61(5)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004; Sheldrick, 2003)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  'XCIF (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker ApexII CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11179
_diffrn_reflns_theta_full        29.03
_diffrn_reflns_theta_max         29.03
_diffrn_reflns_theta_min         2.05
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
Data scaled with SADABS using "no absorption" option.

Sheldrick, G. M. (2004) SADABS, University of G\"ottingen, Germany.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method
;
'dissolved in warm ethyl acetate, hexanes added, cooled to 277 K'
;
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_thermal_history   'cooled to 277 K'
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4182
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.2852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1103
_reflns_number_gt                3689
_reflns_number_total             4182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0701987si20070202_032012_2.cif
_cod_data_source_block           bcn189_0m
_cod_database_code               4022912