#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/68/2016898.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_2016898
loop_
_publ_author_name
'Booth, B. L.'
'Pritchard, R. G.'
'Freitas, A. P.'
'Proença, M. F. J. R. P.'
_publ_section_title
;2-Methyl-4-oxo-3H,5H-6-imidazo[3,4-b][1,2,4]triazepinecarbonitrile:
 condensation product of a β-keto ester with
 1,5-diamino-4-imidazolecarbonitrile under basic conditions
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1693
_journal_page_last               1694
_journal_paper_doi               10.1107/S0108270193002896
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C8 H7 N5 O1'
_chemical_formula_sum            'C8 H7 N5 O'
_chemical_formula_weight         189.18
_chemical_name_systematic
;
2-Methyl-4-oxo-3H,5H-6-imidazo[3,4-b]-[1,2,4]triazepinecarbonitrile
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.314(4)
_cell_length_b                   10.274(3)
_cell_length_c                   14.422(4)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      14.5
_cell_volume                     1824.6(9)
_computing_cell_refinement       'Enraf-Nonius diffractometer control'
_computing_data_collection       'Enraf-Nonius diffractometer control'
_computing_data_reduction
'TEXSAN PROCESS (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    'TEXSAN ORTEPII (Johnson, 1976)'
_computing_publication_material  'TEXSAN FINISH'
_computing_structure_refinement  'TEXSAN LS'
_computing_structure_solution    'TEXSAN Mithril (Gilmore, 1984)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       CAD-4
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5791
_diffrn_reflns_theta_max         24.0636
_diffrn_reflns_theta_min         1.0
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.0929
_exptl_absorpt_correction_type   none?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       needle
_exptl_crystal_F_000             784.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         -0.26029
_refine_diff_density_min         0.21624
_refine_ls_extinction_coef       18E-7(2)
_refine_ls_extinction_method     'Zachariasen type 2 Gaussian isotropic'
_refine_ls_goodness_of_fit_obs   1.148
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         987
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0437
_refine_ls_shift/esd_max         0.0003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0425
_reflns_number_observed          987
_reflns_number_total             1683
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            al1045.cif
_cod_data_source_block           al1045_structure_1_of_1
_cod_original_cell_volume        1824.0(10)
_cod_original_sg_symbol_H-M      'P b c a '
_cod_original_formula_sum        'C8 H7 N5 O1'
_cod_database_code               2016898
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
0.5-x,0.5+y,z
x,0.5-y,0.5+z
0.5+x,y,0.5-z
-x,-y,-z
0.5+x,0.5-y,-z
-x,0.5+y,0.5-z
0.5-x,-y,0.5+z
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 0.0460(10) 0.0470(10) 0.0311(10) 0.0040(10) -0.0069(9) -0.0018(8)
C2 0.0410(10) 0.0450(10) 0.0420(10) 0.0090(10) -0.0110(10) -0.0080(10)
C3 0.0350(10) 0.0450(10) 0.059(2) -0.0020(10) -0.0100(10) -0.0090(10)
C4 0.0430(10) 0.0360(10) 0.0550(10) -0.0030(10) -0.0060(10) -0.0080(10)
N5 0.0420(10) 0.0288(9) 0.0420(10) -0.0020(10) -0.0044(9) 0.0003(8)
C6 0.0460(10) 0.0330(10) 0.0310(10) -0.0010(10) -0.0050(10) 0.0006(8)
N7 0.0560(10) 0.0346(10) 0.0390(10) -0.0090(10) -0.0085(10) 0.0018(7)
C8 0.0500(10) 0.0350(10) 0.0400(10) -0.0080(10) -0.0060(10) 0.0050(10)
N9 0.0420(10) 0.0336(9) 0.0307(10) -0.0010(10) -0.0039(8) -0.0008(7)
C10 0.0350(10) 0.0290(10) 0.0310(10) 0.0040(10) -0.0015(9) 0.0005(8)
C11 0.059(2) 0.096(3) 0.050(2) 0.004(2) -0.014(2) -0.020(2)
O12 0.0790(10) 0.0400(10) 0.106(2) -0.0180(10) -0.0270(10) 0.0014(9)
C13 0.0500(10) 0.0340(10) 0.0410(10) -0.0020(10) -0.0030(10) -0.0045(10)
N14 0.085(2) 0.0570(10) 0.0340(10) -0.0010(10) -0.0040(10) 0.0003(10)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N1 0.4144(2) 0.6194(2) 0.49400(10) 0.0416
C2 0.3289(2) 0.5518(2) 0.4805(2) 0.0429
C3 0.2527(2) 0.5054(3) 0.5536(2) 0.0465
C4 0.3022(2) 0.4080(2) 0.6194(2) 0.0449
N5 0.3875(2) 0.4530(2) 0.67090(10) 0.0375
C6 0.4718(2) 0.6540(2) 0.73450(10) 0.0367
N7 0.5101(2) 0.7700(2) 0.69790(10) 0.0431
C8 0.4893(2) 0.7630(2) 0.6101(2) 0.0420
N9 0.4393(2) 0.6492(2) 0.58680(10) 0.0354
C10 0.4272(2) 0.5784(2) 0.66640(10) 0.0319
C11 0.3034(3) 0.5210(4) 0.3813(2) 0.0683
O12 0.2711(2) 0.2972(2) 0.6274(2) 0.0750
C13 0.4789(2) 0.6207(2) 0.8299(2) 0.0415
N14 0.4819(2) 0.5893(2) 0.90580(10) 0.0583
H3A 0.230(2) 0.580(2) 0.589(2) 0.048(7)
H3B 0.194(2) 0.467(2) 0.526(2) 0.052(7)
H5 0.416(2) 0.395(2) 0.7180(10) 0.051(7)
H8 0.501(2) 0.826(2) 0.563(2) 0.052(7)
H11A 0.228(3) 0.551(3) 0.372(2) 0.090(10)
H11B 0.308(3) 0.425(3) 0.370(2) 0.093(10)
H11C 0.355(3) 0.563(3) 0.343(2) 0.100(10)
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -1 7
-4 4 1
-3 5 -2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 N9 . . . 116.3(2) yes
N1 C2 C3 . . . 125.9(2) yes
C2 C3 C4 . . . 113.7(2) yes
C3 C4 N5 . . . 115.4(2) yes
C4 N5 C10 . . . 124.2(2) yes
N7 C6 C10 . . . 110.6(2) yes
C6 N7 C8 . . . 104.9(2) yes
N7 C8 N9 . . . 112.2(2) yes
N1 N9 C8 . . . 121.3(2) yes
N1 N9 C10 . . . 131.2(2) yes
C8 N9 C10 . . . 107.4(2) yes
N5 C10 C6 . . . 129.7(2) yes
N5 C10 N9 . . . 125.1(2) yes
C6 C10 N9 . . . 104.9(2) yes
C6 C13 N14 . . . 177.0(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . . 1.276(3) yes
N1 N9 . . 1.406(2) yes
C2 C3 . . 1.490(4) yes
C3 C4 . . 1.508(4) yes
C4 N5 . . 1.367(3) yes
N5 C10 . . 1.381(3) yes
C6 N7 . . 1.385(3) yes
C6 C10 . . 1.367(3) yes
N7 C8 . . 1.295(3) yes
C8 N9 . . 1.363(3) yes
