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_4022911
_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           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.798(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7307(15)
_cell_length_b                   18.003(3)
_cell_length_c                   9.4773(14)
_cell_measurement_reflns_used    9021
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.9079
_cell_measurement_theta_min      2.3628
_cell_volume                     1675.2(4)
_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  'XL (Sheldrick, 2001)'
_computing_structure_solution    'XS (Sheldrick, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa ApexII CCD Diffractometer'
_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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            61680
_diffrn_reflns_theta_full        36.32
_diffrn_reflns_theta_max         36.32
_diffrn_reflns_theta_min         2.07
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
Data scaled using SADABS with the "no absorption" option

Sheldrick, G. M. (2004) SADABS University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method
'dissolved in warm ethyl acetate, added hexanes, cooled to 269 K.'
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_exptl_crystal_thermal_history   'cooled to 269 K'
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         8105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0581P)^2^+0.3015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                6439
_reflns_number_total             8105
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0701987si20070202_032012_1.cif
_cod_data_source_block           bcn203
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022911