##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_journal_date_recd_electronic     2016-10-05
_journal_date_accepted     2016-10-08
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue     10
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616015881
_journal_coeditor_code     SJ4064
_publ_contact_author_name     'Zhaodong Wang'
_publ_contact_author_address
;
Chongqing Key Laboratory of Environmental
Materials & Remediation Technologies,
Chongqing University of Arts and Sciences,
Yongchuan,
Chongqing 402160,
People's Republic of China
;
_publ_contact_author_email     'ouwzdong@qq.com'
_publ_contact_author_fax     '086 02349683963'
_publ_contact_author_phone     '08613896169350'
_publ_section_title
;
N,N'-Bis(pyrazin-2-ylmethyl)pyrazine-2,3-dicarboxamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Wang, Zhaodong'
;\
Chongqing Key Laboratory of \
Environmental Materials & Remediation Technologies
Chongqing University of Arts and Sciences
Yongchuan
Chongqing 402160
People's Republic of China
;
    'Yang, Yanshuang'
;\
Chongqing Key Laboratory of \
Environmental Materials & Remediation Technologies
Chongqing University of Arts and Sciences
Yongchuan
Chongqing 402160
People's Republic of China
;
    'Lin, Huanzhu'
;\
Chongqing Key Laboratory of \
Environmental Materials & Remediation Technologies
Chongqing University of Arts and Sciences
Yongchuan
Chongqing 402160
People's Republic of China
;
_publ_section_synopsis
;
The molecule of the title compound, which has three pyrazine rings linked by
amide units, is V-shaped. Its crystal structure features N---H...O, N---H...N
and C---H...O hydrogen bonds.
;
_chemical_name_systematic
;
N,N'-Bis(pyrazin-2-ylmethyl)pyrazine-2,3-dicarboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H14 N8 O2'
_chemical_formula_sum     'C16 H14 N8 O2'
_chemical_formula_iupac     'C16 H14 N8 O2'
_chemical_formula_weight     350.35
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.1166(18)
_cell_length_b     10.022(2)
_cell_length_c     10.781(2)
_cell_angle_alpha     116.951(2)
_cell_angle_beta     97.130(2)
_cell_angle_gamma     102.195(2)
_cell_volume     830.5(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2164
_cell_measurement_theta_min     2.311
_cell_measurement_theta_max     26.645
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.401
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     364
_exptl_absorpt_coefficient_mu     0.100
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3527
_diffrn_reflns_av_R_equivalents     0.0160
_diffrn_reflns_theta_min     2.190
_diffrn_reflns_theta_max     27.675
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.911
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details     ?
_reflns_number_total     3527
_reflns_number_gt     2595
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0603
_refine_ls_R_factor_gt     0.0405
_refine_ls_wR_factor_gt     0.1167
_refine_ls_wR_factor_ref     0.1318
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     3527
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0759P)²+0.0242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.151
_refine_diff_density_min     -0.173
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.44574(13) 0.72355(16) 0.68709(12) 0.0573(4) Uani d 1 . .
    O O2 0.72074(13) 1.03109(13) 0.82972(12) 0.0489(3) Uani d 1 . .
    N N1 0.35307(13) 0.81613(15) 0.88449(13) 0.0423(3) Uani d 1 . .
    H H1 0.3740 0.8582 0.9766 0.051 Uiso d 1 . .
    N N2 -0.04468(13) 0.59908(14) 0.66043(13) 0.0385(3) Uani d 1 . .
    N N3 0.0331(2) 0.3695(2) 0.7075(2) 0.0799(6) Uani d 1 . .
    N N4 0.59054(16) 0.72344(19) 0.99377(15) 0.0525(4) Uani d 1 . .
    N N5 0.88003(14) 0.81968(16) 0.94792(13) 0.0432(3) Uani d 1 . .
    N N6 0.84472(14) 0.86414(16) 0.69834(13) 0.0398(3) Uani d 1 . .
    H H6 0.8840 0.7905 0.6898 0.048 Uiso d 1 . .
    N N7 0.68896(18) 0.96134(17) 0.43602(15) 0.0522(4) Uani d 1 . .
    N N8 0.48052(19) 0.6643(2) 0.32238(17) 0.0695(5) Uani d 1 . .
    C C1 0.46175(16) 0.77287(18) 0.81589(15) 0.0379(4) Uani d 1 . .
    C C2 0.20077(16) 0.79296(18) 0.80565(17) 0.0424(4) Uani d 1 . .
    H H2A 0.2119 0.8171 0.7291 0.051 Uiso calc 1 . .
    H H2B 0.1541 0.8659 0.8699 0.051 Uiso calc 1 . .
    C C3 0.09378(16) 0.62856(17) 0.74138(15) 0.0360(3) Uani d 1 . .
    C C4 -0.14353(18) 0.45555(19) 0.60466(18) 0.0490(4) Uani d 1 . .
    H H4 -0.2414 0.4312 0.5482 0.059 Uiso calc 1 . .
    C C5 -0.1042(2) 0.3430(2) 0.6286(2) 0.0665(6) Uani d 1 . .
    H H5 -0.1766 0.2443 0.5879 0.080 Uiso calc 1 . .
    C C6 0.1310(2) 0.5138(2) 0.7640(2) 0.0610(5) Uani d 1 . .
    H H6A 0.2285 0.5379 0.8211 0.073 Uiso calc 1 . .
    C C7 0.60761(16) 0.78146(17) 0.90534(15) 0.0363(3) Uani d 1 . .
    C C8 0.7197(2) 0.7138(2) 1.0583(2) 0.0603(5) Uani d 1 . .
    H H8 0.7136 0.6766 1.1230 0.072 Uiso calc 1 . .
    C C9 0.8614(2) 0.7568(2) 1.03266(18) 0.0517(4) Uani d 1 . .
    H H9 0.9465 0.7416 1.0757 0.062 Uiso calc 1 . .
    C C10 0.75270(16) 0.83414(17) 0.88594(14) 0.0334(3) Uani d 1 . .
    C C11 0.77139(16) 0.91900(18) 0.80107(15) 0.0358(3) Uani d 1 . .
    C C12 0.86012(18) 0.9254(2) 0.60010(17) 0.0454(4) Uani d 1 . .
    H H12A 0.9436 0.8978 0.5560 0.054 Uiso calc 1 . .
    H H12B 0.8884 1.0391 0.6544 0.054 Uiso calc 1 . .
    C C13 0.71396(17) 0.86430(18) 0.48330(15) 0.0397(4) Uani d 1 . .
    C C14 0.5594(2) 0.9103(2) 0.33497(19) 0.0607(5) Uani d 1 . .
    H H14 0.5376 0.9763 0.3013 0.073 Uiso calc 1 . .
    C C15 0.4576(2) 0.7646(3) 0.2793(2) 0.0645(6) Uani d 1 . .
    H H15 0.3686 0.7342 0.2084 0.077 Uiso calc 1 . .
    C C16 0.6093(2) 0.7170(2) 0.42593(19) 0.0561(5) Uani d 1 . .
    H H16 0.6294 0.6515 0.4609 0.067 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 . 1.2210(17) ?
    O2 C11 . 1.2291(18) ?
    N1 C1 . 1.3376(19) ?
    N1 C2 . 1.4479(18) ?
    N1 H1 . 0.8599 ?
    N2 C4 . 1.3328(19) ?
    N2 C3 . 1.3333(18) ?
    N3 C5 . 1.323(3) ?
    N3 C6 . 1.335(2) ?
    N4 C7 . 1.3312(19) ?
    N4 C8 . 1.336(2) ?
    N5 C9 . 1.3327(19) ?
    N5 C10 . 1.3347(18) ?
    N6 C11 . 1.3278(19) ?
    N6 C12 . 1.4523(18) ?
    N6 H6 . 0.8601 ?
    N7 C14 . 1.328(2) ?
    N7 C13 . 1.3311(19) ?
    N8 C15 . 1.326(3) ?
    N8 C16 . 1.335(2) ?
    C1 C7 . 1.5046(19) ?
    C2 C3 . 1.505(2) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C6 . 1.377(2) ?
    C4 C5 . 1.372(3) ?
    C4 H4 . 0.9300 ?
    C5 H5 . 0.9300 ?
    C6 H6A . 0.9300 ?
    C7 C10 . 1.395(2) ?
    C8 C9 . 1.375(3) ?
    C8 H8 . 0.9300 ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.507(2) ?
    C12 C13 . 1.509(2) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 C16 . 1.379(2) ?
    C14 C15 . 1.359(3) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
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
    C1 N1 C2 . . 120.84(13) ?
    C1 N1 H1 . . 119.6 ?
    C2 N1 H1 . . 119.6 ?
    C4 N2 C3 . . 116.98(14) ?
    C5 N3 C6 . . 115.74(17) ?
    C7 N4 C8 . . 115.88(14) ?
    C9 N5 C10 . . 116.27(13) ?
    C11 N6 C12 . . 121.60(13) ?
    C11 N6 H6 . . 119.2 ?
    C12 N6 H6 . . 119.2 ?
    C14 N7 C13 . . 116.96(15) ?
    C15 N8 C16 . . 115.45(17) ?
    O1 C1 N1 . . 123.67(14) ?
    O1 C1 C7 . . 119.96(14) ?
    N1 C1 C7 . . 116.32(13) ?
    N1 C2 C3 . . 113.38(13) ?
    N1 C2 H2A . . 108.9 ?
    C3 C2 H2A . . 108.9 ?
    N1 C2 H2B . . 108.9 ?
    C3 C2 H2B . . 108.9 ?
    H2A C2 H2B . . 107.7 ?
    N2 C3 C6 . . 120.59(14) ?
    N2 C3 C2 . . 115.50(13) ?
    C6 C3 C2 . . 123.90(14) ?
    N2 C4 C5 . . 121.50(16) ?
    N2 C4 H4 . . 119.3 ?
    C5 C4 H4 . . 119.3 ?
    N3 C5 C4 . . 122.44(17) ?
    N3 C5 H5 . . 118.8 ?
    C4 C5 H5 . . 118.8 ?
    N3 C6 C3 . . 122.74(17) ?
    N3 C6 H6A . . 118.6 ?
    C3 C6 H6A . . 118.6 ?
    N4 C7 C10 . . 121.72(14) ?
    N4 C7 C1 . . 116.92(13) ?
    C10 C7 C1 . . 121.09(13) ?
    N4 C8 C9 . . 122.50(15) ?
    N4 C8 H8 . . 118.8 ?
    C9 C8 H8 . . 118.7 ?
    N5 C9 C8 . . 121.79(15) ?
    N5 C9 H9 . . 119.1 ?
    C8 C9 H9 . . 119.1 ?
    N5 C10 C7 . . 121.65(13) ?
    N5 C10 C11 . . 117.86(12) ?
    C7 C10 C11 . . 120.38(12) ?
    O2 C11 N6 . . 124.70(14) ?
    O2 C11 C10 . . 119.93(13) ?
    N6 C11 C10 . . 115.38(13) ?
    N6 C12 C13 . . 113.24(12) ?
    N6 C12 H12A . . 108.9 ?
    C13 C12 H12A . . 108.9 ?
    N6 C12 H12B . . 108.9 ?
    C13 C12 H12B . . 108.9 ?
    H12A C12 H12B . . 107.7 ?
    N7 C13 C16 . . 120.23(15) ?
    N7 C13 C12 . . 116.23(14) ?
    C16 C13 C12 . . 123.54(15) ?
    N7 C14 C15 . . 122.10(17) ?
    N7 C14 H14 . . 119.0 ?
    C15 C14 H14 . . 119.0 ?
    N8 C15 C14 . . 122.35(17) ?
    N8 C15 H15 . . 118.8 ?
    C14 C15 H15 . . 118.8 ?
    N8 C16 C13 . . 122.89(17) ?
    N8 C16 H16 . . 118.6 ?
    C13 C16 H16 . . 118.6 ?
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_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C2 N1 C1 O1 . . . . 5.8(2) ?
    C2 N1 C1 C7 . . . . -171.79(12) ?
    C1 N1 C2 C3 . . . . 81.57(18) ?
    C4 N2 C3 C6 . . . . 0.5(2) ?
    C4 N2 C3 C2 . . . . -178.48(14) ?
    N1 C2 C3 N2 . . . . -176.08(12) ?
    N1 C2 C3 C6 . . . . 5.0(2) ?
    C3 N2 C4 C5 . . . . -0.5(2) ?
    C6 N3 C5 C4 . . . . 0.7(3) ?
    N2 C4 C5 N3 . . . . -0.1(3) ?
    C5 N3 C6 C3 . . . . -0.6(3) ?
    N2 C3 C6 N3 . . . . 0.1(3) ?
    C2 C3 C6 N3 . . . . 178.94(18) ?
    C8 N4 C7 C10 . . . . -2.3(2) ?
    C8 N4 C7 C1 . . . . 171.75(16) ?
    O1 C1 C7 N4 . . . . -132.13(17) ?
    N1 C1 C7 N4 . . . . 45.6(2) ?
    O1 C1 C7 C10 . . . . 42.0(2) ?
    N1 C1 C7 C10 . . . . -140.35(15) ?
    C7 N4 C8 C9 . . . . -1.7(3) ?
    C10 N5 C9 C8 . . . . -2.0(3) ?
    N4 C8 C9 N5 . . . . 4.0(3) ?
    C9 N5 C10 C7 . . . . -2.0(2) ?
    C9 N5 C10 C11 . . . . 174.14(14) ?
    N4 C7 C10 N5 . . . . 4.4(2) ?
    C1 C7 C10 N5 . . . . -169.43(14) ?
    N4 C7 C10 C11 . . . . -171.71(14) ?
    C1 C7 C10 C11 . . . . 14.5(2) ?
    C12 N6 C11 O2 . . . . -5.5(2) ?
    C12 N6 C11 C10 . . . . 174.84(12) ?
    N5 C10 C11 O2 . . . . -125.27(15) ?
    C7 C10 C11 O2 . . . . 50.96(19) ?
    N5 C10 C11 N6 . . . . 54.42(18) ?
    C7 C10 C11 N6 . . . . -129.35(15) ?
    C11 N6 C12 C13 . . . . -77.41(19) ?
    C14 N7 C13 C16 . . . . 1.2(2) ?
    C14 N7 C13 C12 . . . . -178.84(14) ?
    N6 C12 C13 N7 . . . . 148.37(14) ?
    N6 C12 C13 C16 . . . . -31.7(2) ?
    C13 N7 C14 C15 . . . . -1.4(3) ?
    C16 N8 C15 C14 . . . . 1.0(3) ?
    N7 C14 C15 N8 . . . . 0.3(3) ?
    C15 N8 C16 C13 . . . . -1.2(3) ?
    N7 C13 C16 N8 . . . . 0.1(3) ?
    C12 C13 C16 N8 . . . . -179.88(16) ?
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
    N1 H1 O2 2_677 0.86 2.26 2.9940(18) 144
    N6 H6 N2 1_655 0.86 2.06 2.914(2) 174
    C4 H4 O1 2_566 0.93 2.52 3.369(2) 152
    C5 H5 N7 1_445 0.93 2.46 3.359(3) 162
    C14 H14 O2 2_676 0.93 2.56 3.236(2) 130
