#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:38:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178400 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/22/4022252.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4022252
loop_
_publ_author_name
'Gary W. Breton'
'Kenneth L. Martin'
_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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0478P)²+0.0000P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.29503(14) 0.7500 0.85801(6) 0.01526(8) Uani 1 2 d S
N2 N 0.48862(10) 0.67246(4) 0.62811(4) 0.01699(7) Uani 1 1 d .
O1 O 0.27040(11) 0.50952(3) 0.80283(4) 0.02321(8) Uani 1 1 d .
C1 C 0.33755(11) 0.62926(4) 0.76833(5) 0.01589(7) Uani 1 1 d .
C2 C 0.26401(13) 0.67979(5) 0.46723(5) 0.01975(8) Uani 1 1 d .
C3 C 0.18261(19) 0.7500 1.02110(7) 0.02023(11) Uani 1 2 d S
H2 H 0.189(2) 0.6024(8) 0.3990(9) 0.0279(18) Uiso 1 1 d .
H3A H 0.043(3) 0.6700(9) 1.0309(11) 0.039(2) Uiso 1 1 d .
H3B H 0.390(4) 0.7500 1.1027(16) 0.043(3) Uiso 1 2 d S
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0186(2) 0.01449(17) 0.01285(16) 0.000 0.00263(14) 0.000
N2 0.01981(15) 0.01540(13) 0.01598(13) -0.00051(10) 0.00335(10) 0.00137(11)
O1 0.03371(19) 0.01371(12) 0.02181(14) 0.00215(10) 0.00269(12) -0.00137(11)
C1 0.01810(16) 0.01403(13) 0.01518(14) 0.00028(11) 0.00114(11) 0.00088(12)
C2 0.02353(19) 0.02159(18) 0.01424(14) -0.00192(13) 0.00312(12) -0.00052(14)
C3 0.0232(3) 0.0236(3) 0.0147(2) 0.000 0.00548(18) 0.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C1 111.77(5) . 4_575
C1 N1 C3 123.97(2) . .
C1 N1 C3 123.97(2) 4_575 .
C1 N2 C2 119.79(4) . .
C1 N2 N2 106.81(2) . 4_575
C2 N2 N2 87.28(2) . 4_575
O1 C1 N1 127.59(4) . .
O1 C1 N2 125.87(4) . .
N1 C1 N2 106.51(4) . .
C2 C2 N2 92.72(2) 4_575 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3827(5) .
N1 C1 1.3827(5) 4_575
N1 C3 1.4611(7) .
N2 C1 1.4166(5) .
N2 C2 1.4631(5) .
N2 N2 1.4704(7) 4_575
O1 C1 1.2057(5) .
C2 C2 1.3313(9) 4_575
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N2 N2 C2 -120.35(4) . 4_575 4_575
N2 N2 C1 N1 -7.43(4) 4_575 . .
