Are 1,2-Dihydrodiazetes Aromatic? An Experimental and Computational Investigation
Gary W. Breton; Kenneth L. Martin; Journal of Organic Chemistry 67 (2002) 6699–6704; doi:10.1021/jo026082m

data_4022252
_publ_section_title
;
 Are 1,2-Dihydrodiazetes Aromatic? An Experimental and
 Computational Investigation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6699
_journal_page_last               6704
_journal_paper_doi               10.1021/jo026082m
_journal_volume                  67
_journal_year                    2002
_chemical_formula_moiety         C5H5N3O2
_chemical_formula_sum            'C5 H5 N3 O2'
_chemical_formula_weight         139.12
_chemical_melting_point          359
_chemical_name_common            diazetine
_chemical_name_systematic
;
  3-Methyl-1,3,5-triazabicyclo[3.2.0]hept-6-ene-2,4-dione
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 98.3480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.77700(10)
_cell_length_b                   9.4807(2)
_cell_length_c                   8.2024(2)
_cell_measurement_reflns_used    4391
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      45.2215
_cell_measurement_theta_min      2.5095
_cell_volume                     290.604(12)
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT-PLUS (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  '1K 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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14927
_diffrn_reflns_theta_full        53.15
_diffrn_reflns_theta_max         53.15
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.796805
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.092(10)
_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   0.686
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         3490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.686
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                1615
_reflns_number_total             3490
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026082m_s2.cif
_cod_data_source_block           gb98m
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4022252