#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/21/2212192.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_2212192
loop_
_publ_author_name
'Castillejo Merchán, Alejandro'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 Diimidazo[1,5-a;1',5'-d]pyrazine-5,10-dione
;
_journal_coeditor_code           HB2254
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o636
_journal_page_last               o637
_journal_paper_doi               10.1107/S160053680700061X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H4 N4 O2'
_chemical_formula_moiety         'C8 H4 N4 O2'
_chemical_formula_sum            'C8 H4 N4 O2'
_chemical_formula_weight         188.15
_chemical_name_systematic
;
Diimidazo[1,5-a;1',5'-d]pyrazine-5,10-dione
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.23(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.4047(19)
_cell_length_b                   6.9777(18)
_cell_length_c                   9.678(4)
_cell_measurement_reflns_used    2055
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      3.61
_cell_volume                     362.8(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2005)'
_computing_molecular_graphics    'PLATON  (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.674
_diffrn_measured_fraction_theta_max 0.681
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'ω and φ'
_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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1582
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.62
_diffrn_reflns_theta_min         4.79
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.155
_refine_ls_extinction_coef       0.065(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0657P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                338
_reflns_number_total             471
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2254.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2212192
_cod_database_fobs_code          2212192
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+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
O1 0.0451(12) 0.0337(11) 0.0420(12) -0.0017(8) 0.0098(9) 0.0112(9)
N1 0.0344(14) 0.0259(11) 0.0317(12) 0.0024(9) 0.0054(10) -0.0006(9)
N2 0.0376(14) 0.0306(13) 0.0384(13) 0.0038(10) 0.0090(11) 0.0008(10)
C1 0.0329(16) 0.0300(14) 0.0313(14) 0.0020(11) 0.0073(12) -0.0027(11)
C2 0.0371(17) 0.0248(13) 0.0375(15) 0.0032(12) 0.0100(12) 0.0020(11)
C3 0.0300(15) 0.0202(11) 0.0306(13) 0.0009(10) 0.0067(11) 0.0015(10)
C4 0.0326(16) 0.0244(12) 0.0312(14) 0.0008(11) 0.0010(11) 0.0016(11)
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_thermal_displace_type
_atom_site_occupancy
O O1 0.8612(4) -0.2727(3) 0.6735(2) 0.0399(7) Uani 1.000
N N1 0.8136(4) 0.0322(3) 0.5832(2) 0.0305(7) Uani 1.000
N N2 0.5770(4) 0.2850(3) 0.6149(2) 0.0352(8) Uani 1.000
C C1 0.6301(5) 0.1053(4) 0.6531(3) 0.0311(8) Uani 1.000
C C2 0.7343(6) 0.3279(4) 0.5177(3) 0.0327(9) Uani 1.000
C C3 0.8827(5) 0.1761(4) 0.4951(3) 0.0267(8) Uani 1.000
C C4 0.9248(5) -0.1525(3) 0.5953(3) 0.0296(8) Uani 1.000
H H1 0.545(6) 0.027(4) 0.716(3) 0.041(8) Uiso 1.000
H H2 0.733(6) 0.454(4) 0.478(3) 0.044(8) Uiso 1.000
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C3 . 107.0(2) n
C1 N1 C4 . 128.6(2) n
C3 N1 C4 . 124.4(2) n
C1 N2 C2 . 105.4(2) n
N1 C1 N2 . 111.3(2) n
N2 C2 C3 . 111.2(2) n
N1 C3 C2 . 105.1(2) n
N1 C3 C4 3_756 123.3(2) n
C2 C3 C4 3_756 131.6(3) n
O1 C4 N1 . 122.4(2) n
O1 C4 C3 3_756 125.2(2) n
N1 C4 C3 3_756 112.4(2) n
N1 C1 H1 . 121.5(18) no
N2 C1 H1 . 127.1(18) no
N2 C2 H2 . 119.9(19) no
C3 C2 H2 . 128.9(19) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.205(3) n
N1 C1 . 1.359(4) n
N1 C3 . 1.394(4) n
N1 C4 . 1.422(3) n
N2 C1 . 1.330(4) n
N2 C2 . 1.368(4) n
C2 C3 . 1.361(4) n
C3 C4 3_756 1.440(4) n
C1 H1 . 0.97(3) no
C2 H2 . 0.96(3) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C2 3.207(4) 1_545 no
O1 C1 3.400(4) 2_646 no
O1 C1 3.178(4) 2_746 no
O1 N1 3.097(3) 2_746 no
O1 C3 3.372(4) 2_746 no
O1 H1 2.76(3) . no
O1 H2 2.72(3) 1_545 no
O1 H1 2.90(3) 2_646 no
N1 O1 3.097(3) 2_756 no
N1 N1 2.749(3) 3_756 no
N1 C1 3.273(4) 3_656 no
N2 C1 3.440(4) 2_656 no
N2 C2 3.362(4) 3_666 no
N2 C4 3.339(4) 3_656 no
N2 H1 2.49(3) 2_656 no
N2 H2 2.57(3) 3_666 no
C1 O1 3.400(4) 2_656 no
C1 O1 3.178(4) 2_756 no
C1 N2 3.440(4) 2_646 no
C1 N1 3.273(4) 3_656 no
C1 C1 3.466(4) 3_656 no
C1 C3 3.568(4) 3_656 no
C1 C2 3.543(4) 4_555 no
C2 O1 3.207(4) 1_565 no
C2 N2 3.362(4) 3_666 no
C2 C2 3.480(5) 3_666 no
C2 C1 3.543(4) 4_554 no
C3 C1 3.568(4) 3_656 no
C3 O1 3.372(4) 2_756 no
C4 N2 3.339(4) 3_656 no
C2 H2 2.95(3) 3_666 no
H1 O1 2.76(3) . no
H1 O1 2.90(3) 2_656 no
H1 N2 2.49(3) 2_646 no
H2 O1 2.72(3) 1_565 no
H2 N2 2.57(3) 3_666 no
H2 C2 2.95(3) 3_666 no
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
_geom_hbond_publ_flag
C1 H1 N2 2_646 0.97(3) 2.49(3) 3.440(4) 166(3) yes
C2 H2 N2 3_666 0.96(3) 2.57(3) 3.362(4) 140(3) yes
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_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 C1 N2 . . 0.4(3) no
C4 N1 C1 N2 . . 179.1(2) no
C1 N1 C3 C2 . . -0.1(3) no
C1 N1 C3 C4 . 3_756 179.4(3) no
C4 N1 C3 C2 . . -179.0(2) no
C4 N1 C3 C4 . 3_756 0.6(4) no
C1 N1 C4 O1 . . 0.9(4) no
C1 N1 C4 C3 . 3_756 -179.1(3) no
C3 N1 C4 O1 . . 179.4(3) no
C3 N1 C4 C3 . 3_756 -0.5(4) no
C2 N2 C1 N1 . . -0.4(3) no
C1 N2 C2 C3 . . 0.4(3) no
N2 C2 C3 N1 . . -0.1(3) no
N2 C2 C3 C4 . 3_756 -179.6(3) no
N1 C3 C4 O1 3_756 3_756 179.4(3) no
N1 C3 C4 N1 3_756 3_756 -0.5(4) no
C2 C3 C4 O1 3_756 3_756 -1.2(5) no
C2 C3 C4 N1 3_756 3_756 178.9(3) no
