The title compound, C
16H
14N
8O
2, 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
CCDC reference: 1504885
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(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
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
C16H14N8O2 | Z = 2 |
Mr = 350.35 | F(000) = 364 |
Triclinic, P1 | Dx = 1.401 Mg m−3 |
a = 9.1166 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.022 (2) Å | Cell parameters from 2164 reflections |
c = 10.781 (2) Å | θ = 2.3–26.7° |
α = 116.951 (2)° | µ = 0.10 mm−1 |
β = 97.130 (2)° | T = 296 K |
γ = 102.195 (2)° | Block, colourless |
V = 830.5 (3) Å3 | 0.22 × 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 tube | Rint = 0.016 |
Graphite monochromator | θmax = 27.7°, θmin = 2.2° |
φ and ω scans | h = −11→11 |
3527 measured reflections | k = −13→11 |
3527 independent reflections | l = −13→13 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H-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 reflections | Δρmax = 0.15 e Å−3 |
235 parameters | Δρmin = −0.17 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.44574 (13) | 0.72355 (16) | 0.68709 (12) | 0.0573 (4) | |
O2 | 0.72074 (13) | 1.03109 (13) | 0.82972 (12) | 0.0489 (3) | |
N1 | 0.35307 (13) | 0.81613 (15) | 0.88449 (13) | 0.0423 (3) | |
H1 | 0.3740 | 0.8582 | 0.9766 | 0.051* | |
N2 | −0.04468 (13) | 0.59908 (14) | 0.66043 (13) | 0.0385 (3) | |
N3 | 0.0331 (2) | 0.3695 (2) | 0.7075 (2) | 0.0799 (6) | |
N4 | 0.59054 (16) | 0.72344 (19) | 0.99377 (15) | 0.0525 (4) | |
N5 | 0.88003 (14) | 0.81968 (16) | 0.94792 (13) | 0.0432 (3) | |
N6 | 0.84472 (14) | 0.86414 (16) | 0.69834 (13) | 0.0398 (3) | |
H6 | 0.8840 | 0.7905 | 0.6898 | 0.048* | |
N7 | 0.68896 (18) | 0.96134 (17) | 0.43602 (15) | 0.0522 (4) | |
N8 | 0.48052 (19) | 0.6643 (2) | 0.32238 (17) | 0.0695 (5) | |
C1 | 0.46175 (16) | 0.77287 (18) | 0.81589 (15) | 0.0379 (4) | |
C2 | 0.20077 (16) | 0.79296 (18) | 0.80565 (17) | 0.0424 (4) | |
H2A | 0.2119 | 0.8171 | 0.7291 | 0.051* | |
H2B | 0.1541 | 0.8659 | 0.8699 | 0.051* | |
C3 | 0.09378 (16) | 0.62856 (17) | 0.74138 (15) | 0.0360 (3) | |
C4 | −0.14353 (18) | 0.45555 (19) | 0.60466 (18) | 0.0490 (4) | |
H4 | −0.2414 | 0.4312 | 0.5482 | 0.059* | |
C5 | −0.1042 (2) | 0.3430 (2) | 0.6286 (2) | 0.0665 (6) | |
H5 | −0.1766 | 0.2443 | 0.5879 | 0.080* | |
C6 | 0.1310 (2) | 0.5138 (2) | 0.7640 (2) | 0.0610 (5) | |
H6A | 0.2285 | 0.5379 | 0.8211 | 0.073* | |
C7 | 0.60761 (16) | 0.78146 (17) | 0.90534 (15) | 0.0363 (3) | |
C8 | 0.7197 (2) | 0.7138 (2) | 1.0583 (2) | 0.0603 (5) | |
H8 | 0.7136 | 0.6766 | 1.1230 | 0.072* | |
C9 | 0.8614 (2) | 0.7568 (2) | 1.03266 (18) | 0.0517 (4) | |
H9 | 0.9465 | 0.7416 | 1.0757 | 0.062* | |
C10 | 0.75270 (16) | 0.83414 (17) | 0.88594 (14) | 0.0334 (3) | |
C11 | 0.77139 (16) | 0.91900 (18) | 0.80107 (15) | 0.0358 (3) | |
C12 | 0.86012 (18) | 0.9254 (2) | 0.60010 (17) | 0.0454 (4) | |
H12A | 0.9436 | 0.8978 | 0.5560 | 0.054* | |
H12B | 0.8884 | 1.0391 | 0.6544 | 0.054* | |
C13 | 0.71396 (17) | 0.86430 (18) | 0.48330 (15) | 0.0397 (4) | |
C14 | 0.5594 (2) | 0.9103 (2) | 0.33497 (19) | 0.0607 (5) | |
H14 | 0.5376 | 0.9763 | 0.3013 | 0.073* | |
C15 | 0.4576 (2) | 0.7646 (3) | 0.2793 (2) | 0.0645 (6) | |
H15 | 0.3686 | 0.7342 | 0.2084 | 0.077* | |
C16 | 0.6093 (2) | 0.7170 (2) | 0.42593 (19) | 0.0561 (5) | |
H16 | 0.6294 | 0.6515 | 0.4609 | 0.067* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0428 (7) | 0.0868 (9) | 0.0372 (6) | 0.0231 (6) | 0.0054 (5) | 0.0262 (6) |
O2 | 0.0534 (7) | 0.0522 (7) | 0.0530 (7) | 0.0304 (6) | 0.0143 (5) | 0.0292 (6) |
N1 | 0.0275 (6) | 0.0489 (8) | 0.0373 (7) | 0.0097 (6) | 0.0023 (5) | 0.0130 (6) |
N2 | 0.0311 (6) | 0.0396 (7) | 0.0400 (7) | 0.0083 (6) | 0.0054 (5) | 0.0178 (6) |
N3 | 0.0610 (11) | 0.0556 (10) | 0.1300 (16) | 0.0145 (9) | 0.0086 (11) | 0.0567 (11) |
N4 | 0.0498 (8) | 0.0739 (10) | 0.0550 (9) | 0.0270 (7) | 0.0203 (7) | 0.0436 (8) |
N5 | 0.0369 (7) | 0.0564 (8) | 0.0423 (7) | 0.0211 (6) | 0.0057 (6) | 0.0273 (7) |
N6 | 0.0383 (7) | 0.0510 (8) | 0.0449 (7) | 0.0226 (6) | 0.0131 (6) | 0.0311 (6) |
N7 | 0.0629 (9) | 0.0526 (9) | 0.0490 (8) | 0.0239 (7) | 0.0090 (7) | 0.0301 (7) |
N8 | 0.0603 (10) | 0.0770 (12) | 0.0580 (10) | −0.0004 (9) | 0.0033 (8) | 0.0346 (9) |
C1 | 0.0301 (8) | 0.0415 (8) | 0.0363 (8) | 0.0077 (6) | 0.0034 (6) | 0.0170 (7) |
C2 | 0.0281 (8) | 0.0388 (8) | 0.0516 (9) | 0.0095 (6) | 0.0037 (6) | 0.0171 (7) |
C3 | 0.0297 (7) | 0.0378 (8) | 0.0404 (8) | 0.0123 (6) | 0.0079 (6) | 0.0186 (7) |
C4 | 0.0351 (9) | 0.0474 (10) | 0.0492 (9) | 0.0037 (7) | 0.0023 (7) | 0.0173 (8) |
C5 | 0.0553 (12) | 0.0404 (10) | 0.0930 (15) | 0.0037 (9) | 0.0122 (11) | 0.0304 (10) |
C6 | 0.0423 (10) | 0.0547 (11) | 0.0892 (14) | 0.0126 (8) | 0.0000 (9) | 0.0432 (11) |
C7 | 0.0344 (8) | 0.0415 (8) | 0.0331 (7) | 0.0147 (6) | 0.0068 (6) | 0.0176 (6) |
C8 | 0.0671 (12) | 0.0868 (14) | 0.0607 (11) | 0.0385 (11) | 0.0240 (9) | 0.0551 (11) |
C9 | 0.0493 (10) | 0.0729 (12) | 0.0515 (10) | 0.0335 (9) | 0.0106 (8) | 0.0400 (9) |
C10 | 0.0306 (7) | 0.0388 (8) | 0.0303 (7) | 0.0151 (6) | 0.0042 (5) | 0.0156 (6) |
C11 | 0.0275 (7) | 0.0416 (8) | 0.0381 (8) | 0.0122 (6) | 0.0018 (6) | 0.0203 (7) |
C12 | 0.0424 (9) | 0.0545 (10) | 0.0485 (9) | 0.0144 (8) | 0.0123 (7) | 0.0329 (8) |
C13 | 0.0430 (9) | 0.0454 (9) | 0.0382 (8) | 0.0173 (7) | 0.0146 (7) | 0.0241 (7) |
C14 | 0.0647 (12) | 0.0776 (14) | 0.0540 (11) | 0.0323 (11) | 0.0099 (9) | 0.0407 (10) |
C15 | 0.0495 (11) | 0.0973 (17) | 0.0501 (11) | 0.0189 (11) | 0.0059 (8) | 0.0422 (11) |
C16 | 0.0582 (11) | 0.0573 (11) | 0.0551 (10) | 0.0100 (9) | 0.0067 (9) | 0.0348 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.2210 (17) | C2—C3 | 1.505 (2) |
O2—C11 | 1.2291 (18) | C2—H2A | 0.9700 |
N1—C1 | 1.3376 (19) | C2—H2B | 0.9700 |
N1—C2 | 1.4479 (18) | C3—C6 | 1.377 (2) |
N1—H1 | 0.8599 | C4—C5 | 1.372 (3) |
N2—C4 | 1.3328 (19) | C4—H4 | 0.9300 |
N2—C3 | 1.3333 (18) | C5—H5 | 0.9300 |
N3—C5 | 1.323 (3) | C6—H6A | 0.9300 |
N3—C6 | 1.335 (2) | C7—C10 | 1.395 (2) |
N4—C7 | 1.3312 (19) | C8—C9 | 1.375 (3) |
N4—C8 | 1.336 (2) | C8—H8 | 0.9300 |
N5—C9 | 1.3327 (19) | C9—H9 | 0.9300 |
N5—C10 | 1.3347 (18) | C10—C11 | 1.507 (2) |
N6—C11 | 1.3278 (19) | C12—C13 | 1.509 (2) |
N6—C12 | 1.4523 (18) | C12—H12A | 0.9700 |
N6—H6 | 0.8601 | C12—H12B | 0.9700 |
N7—C14 | 1.328 (2) | C13—C16 | 1.379 (2) |
N7—C13 | 1.3311 (19) | C14—C15 | 1.359 (3) |
N8—C15 | 1.326 (3) | C14—H14 | 0.9300 |
N8—C16 | 1.335 (2) | C15—H15 | 0.9300 |
C1—C7 | 1.5046 (19) | C16—H16 | 0.9300 |
| | | |
C1—N1—C2 | 120.84 (13) | N4—C7—C10 | 121.72 (14) |
C1—N1—H1 | 119.6 | N4—C7—C1 | 116.92 (13) |
C2—N1—H1 | 119.6 | C10—C7—C1 | 121.09 (13) |
C4—N2—C3 | 116.98 (14) | N4—C8—C9 | 122.50 (15) |
C5—N3—C6 | 115.74 (17) | N4—C8—H8 | 118.8 |
C7—N4—C8 | 115.88 (14) | C9—C8—H8 | 118.7 |
C9—N5—C10 | 116.27 (13) | N5—C9—C8 | 121.79 (15) |
C11—N6—C12 | 121.60 (13) | N5—C9—H9 | 119.1 |
C11—N6—H6 | 119.2 | C8—C9—H9 | 119.1 |
C12—N6—H6 | 119.2 | N5—C10—C7 | 121.65 (13) |
C14—N7—C13 | 116.96 (15) | N5—C10—C11 | 117.86 (12) |
C15—N8—C16 | 115.45 (17) | C7—C10—C11 | 120.38 (12) |
O1—C1—N1 | 123.67 (14) | O2—C11—N6 | 124.70 (14) |
O1—C1—C7 | 119.96 (14) | O2—C11—C10 | 119.93 (13) |
N1—C1—C7 | 116.32 (13) | N6—C11—C10 | 115.38 (13) |
N1—C2—C3 | 113.38 (13) | N6—C12—C13 | 113.24 (12) |
N1—C2—H2A | 108.9 | N6—C12—H12A | 108.9 |
C3—C2—H2A | 108.9 | C13—C12—H12A | 108.9 |
N1—C2—H2B | 108.9 | N6—C12—H12B | 108.9 |
C3—C2—H2B | 108.9 | C13—C12—H12B | 108.9 |
H2A—C2—H2B | 107.7 | H12A—C12—H12B | 107.7 |
N2—C3—C6 | 120.59 (14) | N7—C13—C16 | 120.23 (15) |
N2—C3—C2 | 115.50 (13) | N7—C13—C12 | 116.23 (14) |
C6—C3—C2 | 123.90 (14) | C16—C13—C12 | 123.54 (15) |
N2—C4—C5 | 121.50 (16) | N7—C14—C15 | 122.10 (17) |
N2—C4—H4 | 119.3 | N7—C14—H14 | 119.0 |
C5—C4—H4 | 119.3 | C15—C14—H14 | 119.0 |
N3—C5—C4 | 122.44 (17) | N8—C15—C14 | 122.35 (17) |
N3—C5—H5 | 118.8 | N8—C15—H15 | 118.8 |
C4—C5—H5 | 118.8 | C14—C15—H15 | 118.8 |
N3—C6—C3 | 122.74 (17) | N8—C16—C13 | 122.89 (17) |
N3—C6—H6A | 118.6 | N8—C16—H16 | 118.6 |
C3—C6—H6A | 118.6 | C13—C16—H16 | 118.6 |
| | | |
C2—N1—C1—O1 | 5.8 (2) | C9—N5—C10—C11 | 174.14 (14) |
C2—N1—C1—C7 | −171.79 (12) | N4—C7—C10—N5 | 4.4 (2) |
C1—N1—C2—C3 | 81.57 (18) | C1—C7—C10—N5 | −169.43 (14) |
C4—N2—C3—C6 | 0.5 (2) | N4—C7—C10—C11 | −171.71 (14) |
C4—N2—C3—C2 | −178.48 (14) | C1—C7—C10—C11 | 14.5 (2) |
N1—C2—C3—N2 | −176.08 (12) | C12—N6—C11—O2 | −5.5 (2) |
N1—C2—C3—C6 | 5.0 (2) | C12—N6—C11—C10 | 174.84 (12) |
C3—N2—C4—C5 | −0.5 (2) | N5—C10—C11—O2 | −125.27 (15) |
C6—N3—C5—C4 | 0.7 (3) | C7—C10—C11—O2 | 50.96 (19) |
N2—C4—C5—N3 | −0.1 (3) | N5—C10—C11—N6 | 54.42 (18) |
C5—N3—C6—C3 | −0.6 (3) | C7—C10—C11—N6 | −129.35 (15) |
N2—C3—C6—N3 | 0.1 (3) | C11—N6—C12—C13 | −77.41 (19) |
C2—C3—C6—N3 | 178.94 (18) | C14—N7—C13—C16 | 1.2 (2) |
C8—N4—C7—C10 | −2.3 (2) | C14—N7—C13—C12 | −178.84 (14) |
C8—N4—C7—C1 | 171.75 (16) | N6—C12—C13—N7 | 148.37 (14) |
O1—C1—C7—N4 | −132.13 (17) | N6—C12—C13—C16 | −31.7 (2) |
N1—C1—C7—N4 | 45.6 (2) | C13—N7—C14—C15 | −1.4 (3) |
O1—C1—C7—C10 | 42.0 (2) | C16—N8—C15—C14 | 1.0 (3) |
N1—C1—C7—C10 | −140.35 (15) | N7—C14—C15—N8 | 0.3 (3) |
C7—N4—C8—C9 | −1.7 (3) | C15—N8—C16—C13 | −1.2 (3) |
C10—N5—C9—C8 | −2.0 (3) | N7—C13—C16—N8 | 0.1 (3) |
N4—C8—C9—N5 | 4.0 (3) | C12—C13—C16—N8 | −179.88 (16) |
C9—N5—C10—C7 | −2.0 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.26 | 2.9940 (18) | 144 |
N6—H6···N2ii | 0.86 | 2.06 | 2.914 (2) | 174 |
C4—H4···O1iii | 0.93 | 2.52 | 3.369 (2) | 152 |
C5—H5···N7iv | 0.93 | 2.46 | 3.359 (3) | 162 |
C14—H14···O2v | 0.93 | 2.56 | 3.236 (2) | 130 |
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (iv) x−1, y−1, z; (v) −x+1, −y+2, −z+1. |