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The title compound, C16H14N8O2, was prepared by a condensation reaction between the dimethyl ester of pyrazine-2,3-di­carb­oxy­lic acid and an excess of 2-(amino­meth­yl)pyrazine. The mol­ecule is approximately V-shaped with the central pyrazine ring joined through amide linkages to two pyrazin-2-ylmethyl substituents. In the crystal, molecules are linked by N—H...O, N—H...N and C—H...O hydrogen bonds, forming a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616015881/sj4064sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314616015881/sj4064Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616015881/sj4064Isup3.cml
Supplementary material

CCDC reference: 1504885

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.132
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of N3 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 19 Report PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers .... 1 Check
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.002 Degree PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 321 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 5 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

N,N'-Bis(pyrazin-2-ylmethyl)pyrazine-2,3-dicarboxamide top
Crystal data top
C16H14N8O2Z = 2
Mr = 350.35F(000) = 364
Triclinic, P1Dx = 1.401 Mg m3
a = 9.1166 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.022 (2) ÅCell parameters from 2164 reflections
c = 10.781 (2) Åθ = 2.3–26.7°
α = 116.951 (2)°µ = 0.10 mm1
β = 97.130 (2)°T = 296 K
γ = 102.195 (2)°Block, colourless
V = 830.5 (3) Å30.22 × 0.20 × 0.20 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
2595 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 27.7°, θmin = 2.2°
φ and ω scansh = 1111
3527 measured reflectionsk = 1311
3527 independent reflectionsl = 1313
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0759P)2 + 0.0242P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3527 reflectionsΔρmax = 0.15 e Å3
235 parametersΔρmin = 0.17 e Å3
Special details top

Geometry. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.44574 (13)0.72355 (16)0.68709 (12)0.0573 (4)
O20.72074 (13)1.03109 (13)0.82972 (12)0.0489 (3)
N10.35307 (13)0.81613 (15)0.88449 (13)0.0423 (3)
H10.37400.85820.97660.051*
N20.04468 (13)0.59908 (14)0.66043 (13)0.0385 (3)
N30.0331 (2)0.3695 (2)0.7075 (2)0.0799 (6)
N40.59054 (16)0.72344 (19)0.99377 (15)0.0525 (4)
N50.88003 (14)0.81968 (16)0.94792 (13)0.0432 (3)
N60.84472 (14)0.86414 (16)0.69834 (13)0.0398 (3)
H60.88400.79050.68980.048*
N70.68896 (18)0.96134 (17)0.43602 (15)0.0522 (4)
N80.48052 (19)0.6643 (2)0.32238 (17)0.0695 (5)
C10.46175 (16)0.77287 (18)0.81589 (15)0.0379 (4)
C20.20077 (16)0.79296 (18)0.80565 (17)0.0424 (4)
H2A0.21190.81710.72910.051*
H2B0.15410.86590.86990.051*
C30.09378 (16)0.62856 (17)0.74138 (15)0.0360 (3)
C40.14353 (18)0.45555 (19)0.60466 (18)0.0490 (4)
H40.24140.43120.54820.059*
C50.1042 (2)0.3430 (2)0.6286 (2)0.0665 (6)
H50.17660.24430.58790.080*
C60.1310 (2)0.5138 (2)0.7640 (2)0.0610 (5)
H6A0.22850.53790.82110.073*
C70.60761 (16)0.78146 (17)0.90534 (15)0.0363 (3)
C80.7197 (2)0.7138 (2)1.0583 (2)0.0603 (5)
H80.71360.67661.12300.072*
C90.8614 (2)0.7568 (2)1.03266 (18)0.0517 (4)
H90.94650.74161.07570.062*
C100.75270 (16)0.83414 (17)0.88594 (14)0.0334 (3)
C110.77139 (16)0.91900 (18)0.80107 (15)0.0358 (3)
C120.86012 (18)0.9254 (2)0.60010 (17)0.0454 (4)
H12A0.94360.89780.55600.054*
H12B0.88841.03910.65440.054*
C130.71396 (17)0.86430 (18)0.48330 (15)0.0397 (4)
C140.5594 (2)0.9103 (2)0.33497 (19)0.0607 (5)
H140.53760.97630.30130.073*
C150.4576 (2)0.7646 (3)0.2793 (2)0.0645 (6)
H150.36860.73420.20840.077*
C160.6093 (2)0.7170 (2)0.42593 (19)0.0561 (5)
H160.62940.65150.46090.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0428 (7)0.0868 (9)0.0372 (6)0.0231 (6)0.0054 (5)0.0262 (6)
O20.0534 (7)0.0522 (7)0.0530 (7)0.0304 (6)0.0143 (5)0.0292 (6)
N10.0275 (6)0.0489 (8)0.0373 (7)0.0097 (6)0.0023 (5)0.0130 (6)
N20.0311 (6)0.0396 (7)0.0400 (7)0.0083 (6)0.0054 (5)0.0178 (6)
N30.0610 (11)0.0556 (10)0.1300 (16)0.0145 (9)0.0086 (11)0.0567 (11)
N40.0498 (8)0.0739 (10)0.0550 (9)0.0270 (7)0.0203 (7)0.0436 (8)
N50.0369 (7)0.0564 (8)0.0423 (7)0.0211 (6)0.0057 (6)0.0273 (7)
N60.0383 (7)0.0510 (8)0.0449 (7)0.0226 (6)0.0131 (6)0.0311 (6)
N70.0629 (9)0.0526 (9)0.0490 (8)0.0239 (7)0.0090 (7)0.0301 (7)
N80.0603 (10)0.0770 (12)0.0580 (10)0.0004 (9)0.0033 (8)0.0346 (9)
C10.0301 (8)0.0415 (8)0.0363 (8)0.0077 (6)0.0034 (6)0.0170 (7)
C20.0281 (8)0.0388 (8)0.0516 (9)0.0095 (6)0.0037 (6)0.0171 (7)
C30.0297 (7)0.0378 (8)0.0404 (8)0.0123 (6)0.0079 (6)0.0186 (7)
C40.0351 (9)0.0474 (10)0.0492 (9)0.0037 (7)0.0023 (7)0.0173 (8)
C50.0553 (12)0.0404 (10)0.0930 (15)0.0037 (9)0.0122 (11)0.0304 (10)
C60.0423 (10)0.0547 (11)0.0892 (14)0.0126 (8)0.0000 (9)0.0432 (11)
C70.0344 (8)0.0415 (8)0.0331 (7)0.0147 (6)0.0068 (6)0.0176 (6)
C80.0671 (12)0.0868 (14)0.0607 (11)0.0385 (11)0.0240 (9)0.0551 (11)
C90.0493 (10)0.0729 (12)0.0515 (10)0.0335 (9)0.0106 (8)0.0400 (9)
C100.0306 (7)0.0388 (8)0.0303 (7)0.0151 (6)0.0042 (5)0.0156 (6)
C110.0275 (7)0.0416 (8)0.0381 (8)0.0122 (6)0.0018 (6)0.0203 (7)
C120.0424 (9)0.0545 (10)0.0485 (9)0.0144 (8)0.0123 (7)0.0329 (8)
C130.0430 (9)0.0454 (9)0.0382 (8)0.0173 (7)0.0146 (7)0.0241 (7)
C140.0647 (12)0.0776 (14)0.0540 (11)0.0323 (11)0.0099 (9)0.0407 (10)
C150.0495 (11)0.0973 (17)0.0501 (11)0.0189 (11)0.0059 (8)0.0422 (11)
C160.0582 (11)0.0573 (11)0.0551 (10)0.0100 (9)0.0067 (9)0.0348 (9)
Geometric parameters (Å, º) top
O1—C11.2210 (17)C2—C31.505 (2)
O2—C111.2291 (18)C2—H2A0.9700
N1—C11.3376 (19)C2—H2B0.9700
N1—C21.4479 (18)C3—C61.377 (2)
N1—H10.8599C4—C51.372 (3)
N2—C41.3328 (19)C4—H40.9300
N2—C31.3333 (18)C5—H50.9300
N3—C51.323 (3)C6—H6A0.9300
N3—C61.335 (2)C7—C101.395 (2)
N4—C71.3312 (19)C8—C91.375 (3)
N4—C81.336 (2)C8—H80.9300
N5—C91.3327 (19)C9—H90.9300
N5—C101.3347 (18)C10—C111.507 (2)
N6—C111.3278 (19)C12—C131.509 (2)
N6—C121.4523 (18)C12—H12A0.9700
N6—H60.8601C12—H12B0.9700
N7—C141.328 (2)C13—C161.379 (2)
N7—C131.3311 (19)C14—C151.359 (3)
N8—C151.326 (3)C14—H140.9300
N8—C161.335 (2)C15—H150.9300
C1—C71.5046 (19)C16—H160.9300
C1—N1—C2120.84 (13)N4—C7—C10121.72 (14)
C1—N1—H1119.6N4—C7—C1116.92 (13)
C2—N1—H1119.6C10—C7—C1121.09 (13)
C4—N2—C3116.98 (14)N4—C8—C9122.50 (15)
C5—N3—C6115.74 (17)N4—C8—H8118.8
C7—N4—C8115.88 (14)C9—C8—H8118.7
C9—N5—C10116.27 (13)N5—C9—C8121.79 (15)
C11—N6—C12121.60 (13)N5—C9—H9119.1
C11—N6—H6119.2C8—C9—H9119.1
C12—N6—H6119.2N5—C10—C7121.65 (13)
C14—N7—C13116.96 (15)N5—C10—C11117.86 (12)
C15—N8—C16115.45 (17)C7—C10—C11120.38 (12)
O1—C1—N1123.67 (14)O2—C11—N6124.70 (14)
O1—C1—C7119.96 (14)O2—C11—C10119.93 (13)
N1—C1—C7116.32 (13)N6—C11—C10115.38 (13)
N1—C2—C3113.38 (13)N6—C12—C13113.24 (12)
N1—C2—H2A108.9N6—C12—H12A108.9
C3—C2—H2A108.9C13—C12—H12A108.9
N1—C2—H2B108.9N6—C12—H12B108.9
C3—C2—H2B108.9C13—C12—H12B108.9
H2A—C2—H2B107.7H12A—C12—H12B107.7
N2—C3—C6120.59 (14)N7—C13—C16120.23 (15)
N2—C3—C2115.50 (13)N7—C13—C12116.23 (14)
C6—C3—C2123.90 (14)C16—C13—C12123.54 (15)
N2—C4—C5121.50 (16)N7—C14—C15122.10 (17)
N2—C4—H4119.3N7—C14—H14119.0
C5—C4—H4119.3C15—C14—H14119.0
N3—C5—C4122.44 (17)N8—C15—C14122.35 (17)
N3—C5—H5118.8N8—C15—H15118.8
C4—C5—H5118.8C14—C15—H15118.8
N3—C6—C3122.74 (17)N8—C16—C13122.89 (17)
N3—C6—H6A118.6N8—C16—H16118.6
C3—C6—H6A118.6C13—C16—H16118.6
C2—N1—C1—O15.8 (2)C9—N5—C10—C11174.14 (14)
C2—N1—C1—C7171.79 (12)N4—C7—C10—N54.4 (2)
C1—N1—C2—C381.57 (18)C1—C7—C10—N5169.43 (14)
C4—N2—C3—C60.5 (2)N4—C7—C10—C11171.71 (14)
C4—N2—C3—C2178.48 (14)C1—C7—C10—C1114.5 (2)
N1—C2—C3—N2176.08 (12)C12—N6—C11—O25.5 (2)
N1—C2—C3—C65.0 (2)C12—N6—C11—C10174.84 (12)
C3—N2—C4—C50.5 (2)N5—C10—C11—O2125.27 (15)
C6—N3—C5—C40.7 (3)C7—C10—C11—O250.96 (19)
N2—C4—C5—N30.1 (3)N5—C10—C11—N654.42 (18)
C5—N3—C6—C30.6 (3)C7—C10—C11—N6129.35 (15)
N2—C3—C6—N30.1 (3)C11—N6—C12—C1377.41 (19)
C2—C3—C6—N3178.94 (18)C14—N7—C13—C161.2 (2)
C8—N4—C7—C102.3 (2)C14—N7—C13—C12178.84 (14)
C8—N4—C7—C1171.75 (16)N6—C12—C13—N7148.37 (14)
O1—C1—C7—N4132.13 (17)N6—C12—C13—C1631.7 (2)
N1—C1—C7—N445.6 (2)C13—N7—C14—C151.4 (3)
O1—C1—C7—C1042.0 (2)C16—N8—C15—C141.0 (3)
N1—C1—C7—C10140.35 (15)N7—C14—C15—N80.3 (3)
C7—N4—C8—C91.7 (3)C15—N8—C16—C131.2 (3)
C10—N5—C9—C82.0 (3)N7—C13—C16—N80.1 (3)
N4—C8—C9—N54.0 (3)C12—C13—C16—N8179.88 (16)
C9—N5—C10—C72.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.262.9940 (18)144
N6—H6···N2ii0.862.062.914 (2)174
C4—H4···O1iii0.932.523.369 (2)152
C5—H5···N7iv0.932.463.359 (3)162
C14—H14···O2v0.932.563.236 (2)130
Symmetry codes: (i) x+1, y+2, z+2; (ii) x+1, y, z; (iii) x, y+1, z+1; (iv) x1, y1, z; (v) x+1, y+2, z+1.
 

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