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#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/25/2222597.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_2222597
loop_
_publ_author_name
'Zhang, Ya-Wen'
'Wang, Jian-Quan'
'Cheng, Lin'
_publ_section_title
(Z,Z)-N''-[Amino(pyrazin-2-yl)methylene]pyrazine-2-carbohydrazonamide
_journal_coeditor_code           BT5007
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1941
_journal_paper_doi               10.1107/S1600536809027834
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H10 N8'
_chemical_formula_moiety         'C10 H10 N8'
_chemical_formula_sum            'C10 H10 N8'
_chemical_formula_weight         242.26
_chemical_name_systematic
;
(Z,Z)-N''-[Amino(pyrazin-2-yl)methylene]pyrazine-\
2-carbohydrazonamide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.682(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6576(16)
_cell_length_b                   6.6685(12)
_cell_length_c                   9.6162(18)
_cell_measurement_reflns_used    651
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      3.88
_cell_volume                     550.19(18)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1946
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0383
_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)+(0.0659P)²+0.0834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                844
_reflns_number_total             946
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5007.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222597
_cod_database_fobs_code          2222597
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
C C1 0.71263(17) -0.1470(2) -0.12888(15) 0.0400(4) Uani d . 1 . .
H H1A 0.7177 -0.2641 -0.1806 0.048 Uiso calc R 1 . .
C C2 0.61260(19) 0.1595(2) -0.10119(17) 0.0459(4) Uani d . 1 . .
H H2A 0.5502 0.2669 -0.1353 0.055 Uiso calc R 1 . .
C C3 0.69636(18) 0.1731(2) 0.03029(16) 0.0421(4) Uani d . 1 . .
H H3A 0.6851 0.2866 0.0842 0.050 Uiso calc R 1 . .
C C4 0.80524(15) -0.1312(2) 0.00078(14) 0.0326(4) Uani d . 1 . .
C C5 0.92285(16) -0.2845(2) 0.05271(14) 0.0322(4) Uani d . 1 . .
N N1 0.61789(15) -0.0024(2) -0.18134(13) 0.0462(4) Uani d . 1 . .
N N2 0.79325(14) 0.02862(18) 0.08288(12) 0.0372(4) Uani d . 1 . .
N N3 1.00358(16) -0.2540(2) 0.17988(13) 0.0431(4) Uani d . 1 . .
H H3B 1.071(2) -0.351(3) 0.2148(18) 0.045(4) Uiso d . 1 . .
H H3C 0.974(2) -0.154(3) 0.2320(19) 0.050(5) Uiso d . 1 . .
N N4 0.94266(14) -0.43331(17) -0.03069(11) 0.0356(4) Uani d . 1 . .
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
C1 0.0420(8) 0.0408(8) 0.0350(8) 0.0018(6) -0.0029(6) -0.0042(7)
C2 0.0441(9) 0.0435(9) 0.0475(9) 0.0069(7) -0.0038(7) 0.0066(7)
C3 0.0468(9) 0.0355(8) 0.0426(9) 0.0047(6) 0.0013(7) -0.0023(7)
C4 0.0353(8) 0.0329(8) 0.0295(7) -0.0030(6) 0.0039(6) 0.0006(6)
C5 0.0363(8) 0.0316(7) 0.0280(7) -0.0025(6) 0.0017(6) 0.0015(6)
N1 0.0459(8) 0.0486(8) 0.0405(8) 0.0040(6) -0.0078(6) 0.0010(6)
N2 0.0429(7) 0.0339(7) 0.0335(7) 0.0024(5) -0.0002(5) -0.0018(5)
N3 0.0534(9) 0.0409(8) 0.0317(7) 0.0145(6) -0.0068(6) -0.0050(6)
N4 0.0425(7) 0.0312(7) 0.0313(7) 0.0042(5) -0.0016(5) -0.0001(5)
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'
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_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C4 . . 122.66(14) ?
N1 C1 H1A . . 118.7 ?
C4 C1 H1A . . 118.7 ?
N1 C2 C3 . . 122.11(14) ?
N1 C2 H2A . . 118.9 ?
C3 C2 H2A . . 118.9 ?
N2 C3 C2 . . 122.01(14) ?
N2 C3 H3A . . 119.0 ?
C2 C3 H3A . . 119.0 ?
N2 C4 C1 . . 120.49(13) ?
N2 C4 C5 . . 117.03(12) ?
C1 C4 C5 . . 122.46(13) ?
N4 C5 N3 . . 125.59(13) ?
N4 C5 C4 . . 117.36(12) ?
N3 C5 C4 . . 117.01(13) ?
C1 N1 C2 . . 116.02(13) ?
C3 N2 C4 . . 116.52(12) ?
C5 N3 H3B . . 117.6(10) ?
C5 N3 H3C . . 118.3(11) ?
H3B N3 H3C . . 123.0(15) ?
C5 N4 N4 . 3_745 111.61(13) ?
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
C1 N1 . 1.3219(19) ?
C1 C4 . 1.393(2) ?
C1 H1A . 0.9300 ?
C2 N1 . 1.331(2) ?
C2 C3 . 1.374(2) ?
C2 H2A . 0.9300 ?
C3 N2 . 1.3318(19) ?
C3 H3A . 0.9300 ?
C4 N2 . 1.3386(18) ?
C4 C5 . 1.4815(19) ?
C5 N4 . 1.3017(18) ?
C5 N3 . 1.3405(18) ?
N3 H3B . 0.906(18) ?
N3 H3C . 0.893(19) ?
N4 N4 3_745 1.403(2) ?
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
N3 H3B N2 2_745 0.906(18) 2.280(18) 3.0539(18) 143.2(14)
N3 H3C N4 4_556 0.892(19) 2.405(18) 3.1587(18) 142.3(16)
