#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/01/2210142.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210142
loop_
_publ_author_name
'Philip J. Kuehl'
'Carducci, Michael D.'
'Paul B. Myrdal'
_publ_section_title
;
 4-Imino-1,3-diazabicyclo[3.1.0]hexan-2-one
;
_journal_coeditor_code           CF2050
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3688
_journal_page_last               o3690
_journal_paper_doi               10.1107/S1600536806029412
_journal_volume                  62
_journal_year                    2006
_chemical_formula_analytical     'C4 H5 N3 O'
_chemical_formula_iupac          'C4 H5 N3 O'
_chemical_formula_moiety         'C4 H5 N3 O'
_chemical_formula_sum            'C4 H5 N3 O'
_chemical_formula_weight         111.11
_chemical_name_common            Imexon
_chemical_name_systematic
;
4-Imino-1,3-diazabicyclo[3.1.0]hexan-2-one
;
_chemical_temperature_decomposition 438
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.685(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3612(12)
_cell_length_b                   6.5999(6)
_cell_length_c                   7.2077(11)
_cell_measurement_reflns_used    1346
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.12
_cell_measurement_theta_min      3.69
_cell_volume                     478.89(10)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics
'SHELXTL (Bruker, 1997) and MERCURY (Macrae et al.,  2006)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.2220
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13504
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Sheldrick, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.703
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         13504
_refine_ls_number_restraints     318
_refine_ls_restrained_S_all      0.701
_refine_ls_R_factor_all          0.1788
_refine_ls_R_factor_gt           0.0593
_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/[σ²(Fo²)+(0.0342P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1407
_reflns_number_gt                4436
_reflns_number_total             13504
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf2050.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been '438
(dec)'. The value '438 (dec)' was changed to '438'.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' tag was changed to
'_chemical_temperature_decomposition' since the value had been '438
(dec)'. The value '438 (dec)' was changed to '438'.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210142
_cod_database_fobs_code          2210142
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.85631(13) 0.37481(17) 0.35979(19) 0.0370(4) Uani d PDU 0.9683(11) A 1
C C2 0.74670(19) 0.2581(2) 0.2473(3) 0.0377(4) Uani d PDU 0.9683(11) A 1
N N3 0.64292(12) 0.37348(18) 0.14670(19) 0.0373(4) Uani d PDU 0.9683(11) A 1
C C4 0.68131(18) 0.5688(2) 0.1829(2) 0.0340(5) Uani d PDU 0.9683(11) A 1
C C5 0.81695(18) 0.5843(2) 0.3052(2) 0.0356(5) Uani d PDU 0.9683(11) A 1
H H5 0.8400 0.6959 0.4011 0.043 Uiso calc PR 0.9683(11) A 1
C C6 0.92297(15) 0.48639(19) 0.2271(2) 0.0413(5) Uani d PDU 0.9683(11) A 1
H H6B 1.0158 0.5316 0.2775 0.050 Uiso calc PR 0.9683(11) A 1
H H6A 0.9006 0.4466 0.0908 0.050 Uiso calc PR 0.9683(11) A 1
O O7 0.75089(11) 0.07101(11) 0.25220(15) 0.0442(3) Uani d PDU 0.9683(11) A 1
N N8 0.60593(12) 0.72271(16) 0.11440(19) 0.0463(4) Uani d PDU 0.9683(11) A 1
H H8B 0.5262 0.7021 0.0410 0.070 Uiso calc PR 0.9683(11) A 1
H H8A 0.6349 0.8471 0.1416 0.070 Uiso calc PR 0.9683(11) A 1
N N1B 0.64292(12) 0.37348(18) 0.14670(19) 0.0373(4) Uani d PDU 0.0317(11) A 2
C C2B 0.74670(19) 0.2581(2) 0.2473(3) 0.0377(4) Uani d PDU 0.0317(11) A 2
N N3B 0.85631(13) 0.37481(17) 0.35979(19) 0.0370(4) Uani d PDU 0.0317(11) A 2
C C4B 0.81695(18) 0.5843(2) 0.3052(2) 0.0356(5) Uani d PDU 0.0317(11) A 2
C C5B 0.68131(18) 0.5688(2) 0.1829(2) 0.0340(5) Uani d PDU 0.0317(11) A 2
H H5B 0.6532 0.6703 0.0781 0.041 Uiso calc PR 0.0317(11) A 2
C C6B 0.573(3) 0.474(4) 0.271(5) 0.0413(5) Uani d PDU 0.0317(11) A 2
H H6C 0.5967 0.4394 0.4089 0.050 Uiso calc PR 0.0317(11) A 2
H H6D 0.4795 0.5143 0.2188 0.050 Uiso calc PR 0.0317(11) A 2
O O7B 0.75089(11) 0.07101(11) 0.25220(15) 0.0442(3) Uani d PDU 0.0317(11) A 2
N N8B 0.905(3) 0.694(4) 0.408(5) 0.0463(4) Uani d PDU 0.0317(11) A 2
H H8C 0.9716 0.6388 0.4907 0.070 Uiso calc PR 0.0317(11) A 2
H H8D 0.8994 0.8272 0.3969 0.070 Uiso calc PR 0.0317(11) A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0402(10) 0.0252(7) 0.0445(10) 0.0029(7) 0.0079(9) 0.0030(8)
C2 0.0442(10) 0.0368(8) 0.0346(10) -0.0108(13) 0.0145(8) -0.0032(12)
N3 0.0402(10) 0.0245(7) 0.0443(11) 0.0030(7) 0.0039(9) 0.0010(8)
C4 0.0345(12) 0.0357(11) 0.0339(13) 0.0041(10) 0.0127(10) 0.0022(9)
C5 0.0446(12) 0.0166(10) 0.0442(14) -0.0030(9) 0.0074(10) -0.0036(8)
C6 0.0461(11) 0.0312(9) 0.0448(13) -0.0033(8) 0.0074(11) -0.0028(8)
O7 0.0582(7) 0.0201(5) 0.0514(8) -0.0036(6) 0.0073(6) 0.0011(6)
N8 0.0497(9) 0.0231(7) 0.0615(11) 0.0033(7) 0.0036(8) 0.0013(8)
N1B 0.0402(10) 0.0245(7) 0.0443(11) 0.0030(7) 0.0039(9) 0.0010(8)
C2B 0.0442(10) 0.0368(8) 0.0346(10) -0.0108(13) 0.0145(8) -0.0032(12)
N3B 0.0402(10) 0.0252(7) 0.0445(10) 0.0029(7) 0.0079(9) 0.0030(8)
C4B 0.0446(12) 0.0166(10) 0.0442(14) -0.0030(9) 0.0074(10) -0.0036(8)
C5B 0.0345(12) 0.0357(11) 0.0339(13) 0.0041(10) 0.0127(10) 0.0022(9)
C6B 0.0461(11) 0.0312(9) 0.0448(13) -0.0033(8) 0.0074(11) -0.0028(8)
O7B 0.0582(7) 0.0201(5) 0.0514(8) -0.0036(6) 0.0073(6) 0.0011(6)
N8B 0.0497(9) 0.0231(7) 0.0615(11) 0.0033(7) 0.0036(8) 0.0013(8)
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
C2 N1 C5 102.65(12)
C2 N1 C6 108.80(13)
C5 N1 C6 60.47(8)
O7 C2 N3 125.86(17)
O7 C2 N1 119.81(17)
N3 C2 N1 114.30(11)
C4 N3 C2 105.52(13)
N8 C4 N3 123.02(17)
N8 C4 C5 124.93(16)
N3 C4 C5 112.04(15)
N1 C5 C4 105.07(14)
N1 C5 C6 60.78(9)
C4 C5 C6 115.24(14)
N1 C5 H5 120.1
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 N1 58.76(9)
C5 C6 H6B 117.9
N1 C6 H6B 117.9
C5 C6 H6A 117.9
N1 C6 H6A 117.9
H6B C6 H6A 115.1
C4 N8 H8B 120.0
C4 N8 H8A 120.0
H8B N8 H8A 120.0
H6C C6B H6D 115.6
H8C N8B H8D 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.4507(16)
N1 C5 1.4685(15)
N1 C6 1.4990(18)
C2 O7 1.2358(12)
C2 N3 1.3759(16)
N3 C4 1.3562(15)
C4 N8 1.3050(15)
C4 C5 1.4751(15)
C5 C6 1.4944(18)
C5 H5 1.000
C6 H6B 0.990
C6 H6A 0.990
N8 H8B 0.880
N8 H8A 0.880
C6B H6C 0.990
C6B H6D 0.990
N8B H8C 0.880
N8B H8D 0.880
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N8 H8B N3 3_665 0.88 2.01 2.8805(19) 172
N8 H8A O7 1_565 0.88 1.95 2.7966(14) 160
N8B H8D O7 1_565 0.88 2.30 3.02(3) 139
N8B H8C N1 3_766 0.88 1.85 2.68(2) 155
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
C5 N1 C2 O7 176.51(16)
C6 N1 C2 O7 113.73(16)
C5 N1 C2 N3 -5.42(19)
C6 N1 C2 N3 -68.21(17)
O7 C2 N3 C4 179.98(17)
N1 C2 N3 C4 2.05(19)
C2 N3 C4 N8 -178.33(15)
C2 N3 C4 C5 2.37(16)
C2 N1 C5 C4 6.20(14)
C6 N1 C5 C4 110.82(13)
C2 N1 C5 C6 -104.62(14)
N8 C4 C5 N1 175.03(16)
N3 C4 C5 N1 -5.68(14)
N8 C4 C5 C6 -120.57(17)
N3 C4 C5 C6 58.72(16)
C4 C5 C6 N1 -93.76(15)
C2 N1 C6 C5 94.19(13)
