Download citation
Download citation
link to html
The title compound, C18H16N6O2, can be crystallized in two polymorphic forms, viz. orthorhombic, described here, and triclinic. In the orthorhombic polymorph, both 2-pyridyl­methyl moieties lie out of the plane of the pyrazine ring by ca 80°. One amide moiety lies in the plane of the pyrazine ring, while the other is almost perpendicular to the pyrazine ring. This structure contrasts with that of the triclinic polymorph, which is L-shaped, with one of the (2-pyridyl­methyl)­amide substituents lying almost in the plane of the pyrazine ring because of the presence of a bifurcated (N—H...N,N′) intramolecular hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680400008X/cv6257sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680400008X/cv6257Isup2.hkl
Contains datablock I

CCDC reference: 234869

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.079
  • Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C12 = 5.30 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2003); cell refinement: X-AREA; data reduction: X-RED32 Stoe & Cie, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C18H16N6O2F(000) = 1456
Mr = 348.37Dx = 1.401 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 15934 reflections
a = 8.5131 (6) Åθ = 1.3–25.6°
b = 31.862 (2) ŵ = 0.10 mm1
c = 12.1757 (6) ÅT = 153 K
V = 3302.6 (4) Å3Block, colourless
Z = 80.50 × 0.50 × 0.40 mm
Data collection top
Stoe IPDS-II
diffractometer
2456 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
Graphite monochromatorθmax = 25.5°, θmin = 1.3°
ω scansh = 107
18389 measured reflectionsk = 3838
3034 independent reflectionsl = 1414
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032All H-atom parameters refined
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.1168P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3034 reflectionsΔρmax = 0.17 e Å3
300 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: shelxl97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0087 (9)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.48512 (11)0.11895 (3)0.67140 (7)0.0331 (3)
O20.66545 (11)0.11705 (3)0.44520 (8)0.0328 (3)
N10.15489 (13)0.14818 (3)0.51065 (9)0.0316 (3)
N20.33433 (14)0.11150 (3)0.34397 (9)0.0347 (4)
N30.27131 (14)0.15786 (3)0.71466 (9)0.0318 (3)
N40.47626 (15)0.22332 (3)0.76079 (11)0.0393 (4)
N50.55206 (13)0.05570 (3)0.49747 (9)0.0280 (3)
N60.76169 (13)0.02198 (3)0.42001 (9)0.0291 (3)
C10.29800 (15)0.13237 (3)0.53071 (10)0.0264 (3)
C20.38618 (15)0.11353 (3)0.44781 (10)0.0272 (4)
C30.19148 (18)0.12732 (4)0.32535 (12)0.0372 (4)
C40.10223 (17)0.14503 (4)0.40816 (12)0.0363 (4)
C50.36065 (15)0.13594 (3)0.64586 (10)0.0265 (3)
C60.31589 (17)0.16569 (4)0.82746 (11)0.0345 (4)
C70.39115 (15)0.20801 (4)0.84357 (11)0.0307 (4)
C80.37539 (19)0.22895 (4)0.94271 (12)0.0400 (5)
C90.4489 (2)0.26717 (4)0.95676 (15)0.0507 (5)
C100.5344 (2)0.28365 (4)0.87083 (15)0.0501 (5)
C110.5456 (2)0.26067 (4)0.77576 (16)0.0478 (5)
C120.54885 (15)0.09581 (4)0.46547 (10)0.0272 (4)
C130.70008 (16)0.03740 (4)0.53576 (11)0.0297 (4)
C140.79668 (15)0.01783 (3)0.44534 (10)0.0260 (3)
C150.91649 (16)0.03958 (4)0.39401 (11)0.0340 (4)
C161.00657 (17)0.01966 (4)0.31531 (12)0.0360 (4)
C170.97450 (16)0.02165 (4)0.29072 (11)0.0311 (4)
C180.85102 (15)0.04081 (4)0.34334 (11)0.0305 (4)
H30.157 (2)0.1258 (5)0.2487 (16)0.051 (4)*
H3N0.182 (2)0.1687 (5)0.6879 (14)0.051 (5)*
H40.002 (2)0.1566 (5)0.3932 (13)0.044 (4)*
H5N0.456 (2)0.0453 (4)0.5211 (13)0.042 (4)*
H6A0.221 (2)0.1630 (4)0.8713 (13)0.046 (4)*
H6B0.3944 (19)0.1431 (4)0.8504 (12)0.038 (4)*
H80.313 (2)0.2173 (5)0.9989 (15)0.049 (5)*
H90.442 (2)0.2812 (6)1.0290 (16)0.064 (5)*
H100.592 (2)0.3114 (5)0.8761 (14)0.058 (5)*
H110.608 (2)0.2717 (5)0.7115 (15)0.058 (5)*
H13A0.7658 (19)0.0597 (4)0.5710 (12)0.035 (4)*
H13B0.6723 (17)0.0151 (4)0.5890 (12)0.029 (3)*
H150.9327 (19)0.0685 (5)0.4141 (12)0.038 (4)*
H161.093 (2)0.0350 (5)0.2808 (14)0.048 (4)*
H171.0368 (19)0.0376 (4)0.2376 (13)0.037 (4)*
H180.8215 (18)0.0698 (5)0.3263 (12)0.038 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0301 (5)0.0389 (5)0.0304 (5)0.0065 (4)0.0037 (4)0.0014 (4)
O20.0300 (5)0.0349 (4)0.0336 (5)0.0025 (4)0.0040 (4)0.0027 (4)
N10.0278 (6)0.0318 (5)0.0352 (6)0.0033 (4)0.0035 (5)0.0004 (4)
N20.0395 (7)0.0370 (6)0.0275 (6)0.0030 (5)0.0036 (5)0.0007 (4)
N30.0264 (6)0.0393 (6)0.0297 (6)0.0019 (5)0.0001 (5)0.0068 (4)
N40.0409 (7)0.0341 (5)0.0428 (7)0.0011 (5)0.0080 (6)0.0040 (5)
N50.0251 (6)0.0287 (5)0.0303 (6)0.0034 (4)0.0033 (5)0.0007 (4)
N60.0266 (6)0.0317 (5)0.0290 (6)0.0011 (4)0.0016 (5)0.0004 (4)
C10.0256 (6)0.0240 (5)0.0297 (7)0.0005 (4)0.0002 (5)0.0010 (4)
C20.0301 (7)0.0250 (5)0.0265 (7)0.0010 (5)0.0005 (5)0.0008 (4)
C30.0404 (8)0.0402 (7)0.0311 (8)0.0030 (6)0.0094 (7)0.0007 (5)
C40.0332 (8)0.0379 (7)0.0378 (8)0.0047 (6)0.0093 (6)0.0007 (5)
C50.0255 (6)0.0255 (5)0.0285 (7)0.0026 (5)0.0006 (5)0.0003 (4)
C60.0332 (7)0.0445 (7)0.0257 (7)0.0062 (6)0.0051 (6)0.0047 (5)
C70.0262 (7)0.0358 (6)0.0300 (7)0.0060 (5)0.0004 (6)0.0042 (5)
C80.0429 (9)0.0441 (7)0.0329 (8)0.0091 (6)0.0017 (7)0.0075 (6)
C90.0636 (11)0.0402 (7)0.0483 (10)0.0137 (7)0.0163 (9)0.0153 (7)
C100.0543 (10)0.0300 (7)0.0661 (11)0.0038 (6)0.0142 (9)0.0062 (7)
C110.0486 (9)0.0338 (7)0.0610 (11)0.0017 (6)0.0050 (8)0.0003 (7)
C120.0301 (7)0.0307 (6)0.0207 (6)0.0022 (5)0.0023 (5)0.0028 (4)
C130.0296 (7)0.0324 (6)0.0272 (7)0.0050 (5)0.0003 (5)0.0001 (5)
C140.0235 (6)0.0298 (6)0.0246 (6)0.0038 (5)0.0018 (5)0.0021 (4)
C150.0336 (7)0.0295 (6)0.0390 (8)0.0005 (5)0.0051 (6)0.0002 (5)
C160.0301 (7)0.0424 (7)0.0356 (8)0.0026 (6)0.0082 (6)0.0040 (5)
C170.0264 (7)0.0409 (6)0.0259 (7)0.0066 (5)0.0001 (5)0.0018 (5)
C180.0287 (7)0.0329 (6)0.0299 (7)0.0009 (5)0.0006 (6)0.0040 (5)
Geometric parameters (Å, º) top
O1—C51.2299 (15)C8—C91.3798 (19)
O2—C121.2265 (16)C9—C101.379 (2)
N1—C11.3408 (16)C10—C111.373 (2)
N1—C41.3298 (18)C13—C141.5090 (18)
N2—C21.3407 (17)C14—C151.3824 (18)
N2—C31.3358 (19)C15—C161.382 (2)
N3—C51.3297 (16)C16—C171.3772 (18)
N3—C61.4466 (17)C17—C181.3741 (19)
N4—C71.3337 (18)C3—H30.980 (19)
N4—C111.3409 (17)C4—H40.978 (17)
N5—C121.3363 (16)C6—H6A0.972 (17)
N5—C131.4647 (17)C6—H6B1.021 (15)
N6—C141.3389 (14)C8—H80.942 (18)
N6—C181.3453 (17)C9—H90.99 (2)
N3—H3N0.896 (17)C10—H101.013 (16)
N5—H5N0.928 (16)C11—H111.009 (18)
C1—C21.3938 (17)C13—H13A1.001 (14)
C1—C51.5044 (17)C13—H13B0.990 (14)
C2—C121.5109 (18)C15—H150.963 (16)
C3—C41.383 (2)C16—H160.978 (17)
C6—C71.5057 (18)C17—H170.979 (15)
C7—C81.3857 (19)C18—H180.980 (16)
C1—N1—C4116.68 (11)C13—C14—C15121.65 (10)
C2—N2—C3116.20 (11)C14—C15—C16119.52 (12)
C5—N3—C6122.59 (11)C15—C16—C17118.67 (13)
C7—N4—C11117.46 (13)C16—C17—C18118.35 (12)
C12—N5—C13119.41 (11)N6—C18—C17123.91 (12)
C14—N6—C18117.17 (11)N2—C3—H3114.6 (10)
C6—N3—H3N120.1 (11)C4—C3—H3123.4 (10)
C5—N3—H3N117.3 (11)N1—C4—H4116.9 (9)
C13—N5—H5N121.2 (9)C3—C4—H4121.1 (9)
C12—N5—H5N114.5 (9)N3—C6—H6A106.8 (10)
C2—C1—C5121.10 (11)N3—C6—H6B108.1 (8)
N1—C1—C5117.61 (11)C7—C6—H6A111.2 (8)
N1—C1—C2121.28 (11)C7—C6—H6B108.5 (8)
N2—C2—C12114.71 (11)H6A—C6—H6B109.4 (12)
C1—C2—C12123.47 (11)C7—C8—H8119.8 (10)
N2—C2—C1121.76 (11)C9—C8—H8120.9 (10)
N2—C3—C4122.04 (13)C8—C9—H9118.9 (11)
N1—C4—C3121.99 (13)C10—C9—H9122.3 (11)
O1—C5—N3124.38 (12)C9—C10—H10122.7 (10)
O1—C5—C1120.52 (11)C11—C10—H10119.0 (10)
N3—C5—C1115.09 (11)N4—C11—H11115.8 (10)
N3—C6—C7112.94 (11)C10—C11—H11120.3 (10)
N4—C7—C8122.33 (12)N5—C13—H13A109.6 (8)
C6—C7—C8120.23 (12)N5—C13—H13B106.8 (8)
N4—C7—C6117.40 (12)C14—C13—H13A107.5 (9)
C7—C8—C9119.28 (14)C14—C13—H13B108.1 (8)
C8—C9—C10118.79 (15)H13A—C13—H13B111.2 (12)
C9—C10—C11118.26 (13)C14—C15—H15118.1 (9)
N4—C11—C10123.87 (16)C16—C15—H15122.4 (9)
O2—C12—C2120.46 (11)C15—C16—H16119.1 (10)
N5—C12—C2114.68 (11)C17—C16—H16122.2 (10)
O2—C12—N5124.74 (12)C16—C17—H17122.2 (8)
N5—C13—C14113.65 (11)C18—C17—H17119.5 (8)
N6—C14—C13115.99 (11)N6—C18—H18115.0 (9)
N6—C14—C15122.34 (11)C17—C18—H18121.1 (9)
C4—N1—C1—C20.16 (16)C2—C1—C5—N3174.20 (10)
C4—N1—C1—C5179.44 (10)N1—C1—C5—O1173.85 (10)
C1—N1—C4—C31.57 (18)N1—C1—C5—N35.40 (14)
C3—N2—C2—C12.09 (16)C1—C2—C12—O295.14 (15)
C3—N2—C2—C12179.31 (10)N2—C2—C12—O282.03 (14)
C2—N2—C3—C40.37 (18)N2—C2—C12—N594.24 (13)
C6—N3—C5—O12.93 (18)C1—C2—C12—N588.60 (14)
C6—N3—C5—C1177.86 (10)N2—C3—C4—N11.5 (2)
C5—N3—C6—C797.34 (13)N3—C6—C7—N432.27 (17)
C11—N4—C7—C6178.86 (13)N3—C6—C7—C8149.91 (13)
C11—N4—C7—C81.1 (2)C6—C7—C8—C9178.23 (14)
C7—N4—C11—C100.3 (2)N4—C7—C8—C90.5 (2)
C13—N5—C12—O214.69 (19)C7—C8—C9—C100.8 (2)
C13—N5—C12—C2169.22 (11)C8—C9—C10—C111.6 (2)
C12—N5—C13—C1489.76 (13)C9—C10—C11—N41.0 (3)
C18—N6—C14—C13176.90 (11)N5—C13—C14—N685.59 (13)
C18—N6—C14—C151.56 (18)N5—C13—C14—C1595.95 (14)
C14—N6—C18—C170.15 (19)C13—C14—C15—C16176.92 (12)
N1—C1—C2—N22.08 (16)N6—C14—C15—C161.5 (2)
C5—C1—C2—C120.54 (16)C14—C15—C16—C170.4 (2)
N1—C1—C2—C12179.05 (10)C15—C16—C17—C181.9 (2)
C5—C1—C2—N2177.51 (10)C16—C17—C18—N61.9 (2)
C2—C1—C5—O16.56 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···N10.896 (17)2.267 (17)2.6921 (16)108.7 (13)
N3—H3N···N4i0.896 (17)2.547 (17)3.2785 (16)139.2 (14)
N5—H5N···N6ii0.928 (16)2.122 (16)3.0493 (16)178.3 (13)
C3—H3···O2iii0.980 (19)2.378 (19)3.3178 (18)160.5 (14)
C6—H6A···O1i0.972 (17)2.505 (16)3.1855 (17)127.0 (11)
C6—H6B···O11.021 (15)2.437 (15)2.8114 (16)100.7 (9)
C10—H10···O2iv1.013 (16)2.509 (16)3.4749 (17)159.2 (13)
Symmetry codes: (i) x1/2, y, z+3/2; (ii) x+1, y, z+1; (iii) x1/2, y, z+1/2; (iv) x, y+1/2, z+1/2.
Notes: dihedral angles between various aromatic rings in the orthorhombic and triclinic polymorphs of (I); Plane A = pyrazine ring; Plane B = pyridine ring (containing N4); Plane C = pyridine ring (containing N6). top
PolymorphPlane–PlaneAngle (°)PolymorphPlane–PlaneAngle (°)
orthorhombicA–B81.5 (1)triclinicA–B17.8 (2)
A–C80.7 (1)A–C60.5 (2)
B–C25.1 (1)B–C74.1 (2)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds