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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): o544.
Published online 2010 February 6. doi:  10.1107/S1600536810004083
PMCID: PMC2983521

N′-[1-(4-Amino­phen­yl)ethyl]pyrazine-2-carbohydrazide

Abstract

The title compound, C13H13N5O, crystallizes with two mol­ecules in the asymmetric unit. The crystal structure is stabilized by intra­molecular N—H(...)N and N—H(...)O hydrogen bonds. The dihedral angles between the pyrazine ring and the 4-aminolphenyl ring are 2.5 (1) and 6.5 (1)° in the two molecules.

Related literature

For applications of the pyrazine ring system in drug development, see: Du et al. (2009 [triangle]); Dubinina et al. (2006 [triangle]); Ellsworth et al. (2007 [triangle]); Mukaiyama et al. (2007 [triangle]).

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Object name is e-66-0o544-scheme1.jpg

Experimental

Crystal data

  • C13H13N5O
  • M r = 255.28
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o544-efi1.jpg
  • a = 6.9783 (13) Å
  • b = 10.689 (3) Å
  • c = 17.061 (5) Å
  • α = 106.971 (10)°
  • β = 98.499 (4)°
  • γ = 90.174 (14)°
  • V = 1202.3 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 113 K
  • 0.10 × 0.09 × 0.04 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (REQAB; Jacobson, 1998 [triangle]) T min = 0.991, T max = 0.996
  • 9090 measured reflections
  • 4150 independent reflections
  • 2832 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.164
  • S = 1.05
  • 4150 reflections
  • 364 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004083/hg2638sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004083/hg2638Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors would like to thank the Scientific Research Fund of Heilongjiang Provincial Education Department (No. 1153 G043) and the Doctoral Foundation of Northeast Agricultural University (No. 2009RC22). We also thank Professor Hai-bin Song of Nankai University for his contribution to the crystal analysis for this paper.

supplementary crystallographic information

Comment

The pyrazine ring system is a useful structural element in medicinal chemistry and has found broad applications in drug development which can be used as antiproliferative agent (Dubinina et al., 2006), potent CXCR3 antagonists (Du et al., 2009), CB1 antagonists (Ellsworth et al., 2007) and c-Src inhibitory (Mukaiyama et al., 2007). In view of different applications of this class of compounds, we have undertaken a single-crystal structure determination of the title compound. The crystal structure has two independent molecules in the aysmmetric unit, and the dihedral angles between the pyrazine ring and the 4-aminolphenyl ring are 2.5 (1) and 6.5 (1)° in the two molecules (Fig. 1). The crystal structure is stabilized by N—H···O intermolecular hydrogen bonds (between molecules of the 'A' type), each of which are also by N—H···N intermolecular interactions (with molecules of 'B' type) between them (Fig. 2).

Experimental

For the synthesis of N'-(1-(4-aminophenyl)ethylidene) pyrazine-2-carbohydrazide, (I), a mixture of pyrazine-2-carboxylic acid hydrazide (0.01 mol, 1.38 g) and 1-(4-aminophenyl)ethanone (0.01 mol, 1.35 g) in methanol was refluxed for 2 h. The solid material obtained on cooling was filtered, washed with ethanol: ether =1:1, dried and crystallized from methanol (yield 62%). The compound (1.0 mmol, 0.268 g) was dissolved in 95% ethanol (30 ml) and kept at room temperature for one week, after which yellow platelet shaped single crystals formed and were collected and washed with ether for X-ray diffraction analysis.

Refinement

All H atoms were initially located in a difference Fourier map. The C—Hatoms were then constrained to an ideal geometry, with C(CH3)—H distances of 0.98 Å, C(phenyl)—H distances of 0.93 Å and Uiso(H) = 1.2Ueq(C). The amino H atoms were refined freely with N—H distances in the range 0.88–0.97 Å.

Figures

Fig. 1.
The structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
The molecular packing depicting N—H···O and N—H···N intermolecular interactions as dashed lines.

Crystal data

C13H13N5OZ = 4
Mr = 255.28F(000) = 536
Triclinic, P1Dx = 1.410 Mg m3
a = 6.9783 (13) ÅMo Kα radiation, λ = 0.71070 Å
b = 10.689 (3) ÅCell parameters from 2002 reflections
c = 17.061 (5) Åθ = 2.5–27.8°
α = 106.971 (10)°µ = 0.10 mm1
β = 98.499 (4)°T = 113 K
γ = 90.174 (14)°Platelet, yellow
V = 1202.3 (5) Å30.10 × 0.09 × 0.04 mm

Data collection

Rigaku Saturn diffractometer4150 independent reflections
Radiation source: rotating anode2832 reflections with I > 2σ(I)
confocalRint = 0.052
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 2.0°
ω scansh = −8→8
Absorption correction: multi-scan (REQAB; Jacobson, 1998)k = −11→12
Tmin = 0.991, Tmax = 0.996l = −20→20
9090 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0724P)2] where P = (Fo2 + 2Fc2)/3
4150 reflections(Δ/σ)max = 0.001
364 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.29 e Å3

Special details

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.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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)

xyzUiso*/Ueq
C10.8650 (4)0.1637 (3)0.24329 (16)0.0213 (6)
C20.8881 (4)0.0891 (3)0.16283 (16)0.0243 (7)
H20.9195−0.00010.15270.029*
C30.8657 (4)0.1438 (3)0.09828 (17)0.0220 (6)
H30.88230.09130.04450.026*
C40.8193 (4)0.2747 (3)0.11007 (16)0.0197 (6)
C50.7963 (4)0.3486 (3)0.19089 (16)0.0220 (6)
H50.76310.43750.20090.026*
C60.8207 (4)0.2952 (3)0.25550 (17)0.0239 (7)
H60.80740.34830.30960.029*
C70.7939 (4)0.3348 (3)0.04141 (16)0.0217 (6)
C80.8024 (4)0.2514 (3)−0.04611 (16)0.0289 (7)
H8A0.72980.2917−0.08540.043*
H8B0.74510.1638−0.05460.043*
H8C0.93790.2447−0.05520.043*
C90.6961 (4)0.6487 (3)0.02186 (16)0.0217 (6)
C100.6788 (4)0.7066 (3)−0.04848 (16)0.0203 (6)
C110.6397 (4)0.8372 (3)−0.03596 (17)0.0238 (7)
H110.62140.88840.01790.029*
C120.6529 (4)0.8158 (3)−0.17048 (17)0.0268 (7)
H120.64450.8509−0.21590.032*
C130.6926 (4)0.6840 (3)−0.18385 (17)0.0256 (7)
H130.71040.6328−0.23780.031*
C140.4201 (4)0.1709 (3)0.68980 (17)0.0227 (6)
C150.3869 (4)0.0943 (3)0.60680 (17)0.0256 (7)
H150.38570.00160.59360.031*
C160.3557 (4)0.1525 (3)0.54366 (17)0.0249 (7)
H160.33590.09860.48770.030*
C170.3526 (4)0.2884 (3)0.56009 (16)0.0221 (6)
C180.3846 (4)0.3637 (3)0.64354 (17)0.0246 (7)
H180.38360.45640.65690.029*
C190.4175 (4)0.3068 (3)0.70710 (17)0.0250 (7)
H190.43860.36060.76310.030*
C200.3116 (4)0.3502 (3)0.49280 (16)0.0222 (6)
C210.3380 (4)0.2769 (3)0.40568 (17)0.0299 (7)
H21A0.21260.26440.36920.045*
H21B0.38960.19130.40460.045*
H21C0.42890.32710.38650.045*
C220.1804 (4)0.6521 (3)0.46356 (17)0.0242 (7)
C230.1331 (4)0.6910 (3)0.38597 (16)0.0214 (6)
C240.1030 (4)0.8204 (3)0.38957 (17)0.0261 (7)
H240.11260.88390.44240.031*
C250.0467 (4)0.7651 (3)0.24967 (17)0.0262 (7)
H250.01520.78780.19960.031*
C260.0763 (4)0.6349 (3)0.24498 (17)0.0265 (7)
H260.06440.57140.19210.032*
N10.8761 (4)0.1101 (2)0.30779 (15)0.0294 (6)
H1A0.933 (5)0.036 (3)0.3056 (18)0.044*
H1B0.861 (4)0.171 (3)0.361 (2)0.044*
N20.7625 (3)0.4591 (2)0.06300 (13)0.0228 (5)
N30.7388 (3)0.5209 (2)0.00192 (14)0.0224 (6)
H3A0.742 (4)0.482 (3)−0.0522 (17)0.027*
N40.7064 (3)0.6282 (2)−0.12325 (13)0.0228 (5)
N50.6263 (3)0.8945 (2)−0.09690 (14)0.0264 (6)
N60.4577 (4)0.1131 (3)0.75362 (16)0.0289 (6)
H6A0.410 (5)0.029 (3)0.7404 (18)0.043*
H6B0.433 (4)0.168 (3)0.8058 (19)0.043*
N70.2571 (3)0.4699 (2)0.51400 (14)0.0257 (6)
N80.2176 (3)0.5256 (2)0.44979 (14)0.0238 (6)
H80.198 (4)0.475 (3)0.3982 (17)0.029*
N90.1215 (3)0.5968 (2)0.31366 (14)0.0257 (6)
N100.0608 (3)0.8597 (2)0.32169 (14)0.0277 (6)
O10.6759 (3)0.71548 (19)0.09187 (12)0.0328 (5)
O20.1874 (3)0.73296 (19)0.53239 (11)0.0347 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0209 (14)0.0198 (15)0.0229 (16)−0.0025 (11)−0.0002 (11)0.0074 (12)
C20.0294 (15)0.0212 (16)0.0211 (16)0.0025 (12)0.0050 (12)0.0038 (12)
C30.0214 (14)0.0227 (16)0.0206 (15)0.0012 (12)0.0036 (11)0.0044 (12)
C40.0185 (13)0.0181 (15)0.0241 (16)−0.0013 (11)0.0033 (11)0.0086 (12)
C50.0218 (14)0.0180 (15)0.0263 (16)0.0008 (11)0.0031 (12)0.0069 (12)
C60.0284 (15)0.0227 (16)0.0204 (15)0.0025 (12)0.0053 (12)0.0050 (12)
C70.0167 (13)0.0245 (16)0.0220 (15)−0.0024 (11)0.0026 (11)0.0042 (12)
C80.0337 (16)0.0316 (18)0.0224 (16)0.0013 (13)0.0044 (13)0.0092 (13)
C90.0239 (14)0.0208 (16)0.0204 (16)−0.0003 (12)0.0022 (12)0.0066 (12)
C100.0170 (13)0.0212 (15)0.0221 (15)0.0008 (11)0.0043 (11)0.0048 (12)
C110.0236 (15)0.0249 (16)0.0221 (16)−0.0021 (12)0.0019 (12)0.0064 (13)
C120.0265 (15)0.0317 (18)0.0258 (17)0.0006 (13)0.0026 (12)0.0147 (14)
C130.0255 (15)0.0332 (18)0.0192 (15)0.0011 (13)0.0047 (12)0.0088 (13)
C140.0199 (14)0.0238 (16)0.0262 (16)0.0032 (12)0.0066 (12)0.0087 (13)
C150.0293 (16)0.0211 (16)0.0287 (17)0.0026 (12)0.0099 (13)0.0082 (13)
C160.0292 (15)0.0238 (16)0.0215 (16)0.0011 (12)0.0067 (12)0.0050 (12)
C170.0195 (14)0.0248 (16)0.0219 (15)0.0026 (12)0.0046 (11)0.0063 (12)
C180.0248 (15)0.0216 (16)0.0267 (16)0.0031 (12)0.0020 (12)0.0071 (13)
C190.0222 (14)0.0301 (17)0.0205 (15)−0.0007 (12)0.0022 (12)0.0043 (13)
C200.0194 (14)0.0277 (17)0.0197 (15)−0.0007 (12)0.0040 (11)0.0069 (13)
C210.0376 (17)0.0279 (17)0.0244 (17)0.0056 (13)0.0060 (13)0.0074 (13)
C220.0219 (14)0.0234 (16)0.0265 (17)−0.0014 (12)0.0035 (12)0.0061 (13)
C230.0207 (14)0.0235 (16)0.0198 (15)−0.0002 (12)0.0049 (11)0.0053 (12)
C240.0303 (16)0.0268 (17)0.0211 (16)0.0037 (13)0.0058 (12)0.0060 (13)
C250.0258 (15)0.0317 (18)0.0235 (16)0.0078 (13)0.0043 (12)0.0113 (14)
C260.0269 (15)0.0300 (17)0.0203 (16)0.0018 (13)0.0050 (12)0.0036 (13)
N10.0450 (16)0.0207 (15)0.0250 (14)0.0080 (12)0.0097 (12)0.0087 (12)
N20.0246 (13)0.0237 (14)0.0217 (13)0.0013 (10)0.0013 (10)0.0103 (11)
N30.0290 (13)0.0224 (14)0.0166 (13)0.0012 (10)0.0036 (10)0.0073 (11)
N40.0238 (12)0.0244 (13)0.0203 (13)0.0017 (10)0.0044 (10)0.0064 (10)
N50.0277 (13)0.0249 (14)0.0292 (14)−0.0004 (10)0.0057 (10)0.0116 (11)
N60.0358 (15)0.0285 (15)0.0267 (15)0.0041 (12)0.0074 (11)0.0135 (12)
N70.0305 (13)0.0272 (14)0.0224 (13)0.0024 (11)0.0057 (10)0.0110 (11)
N80.0300 (13)0.0231 (14)0.0176 (13)0.0013 (10)0.0028 (10)0.0055 (11)
N90.0250 (12)0.0284 (14)0.0227 (13)0.0024 (10)0.0033 (10)0.0062 (11)
N100.0305 (13)0.0252 (14)0.0289 (14)0.0031 (11)0.0058 (11)0.0096 (11)
O10.0459 (13)0.0313 (12)0.0214 (12)0.0075 (10)0.0080 (9)0.0068 (9)
O20.0509 (14)0.0298 (12)0.0199 (12)0.0042 (10)0.0042 (9)0.0027 (9)

Geometric parameters (Å, °)

C1—N11.374 (3)C15—H150.9500
C1—C61.402 (4)C16—C171.398 (4)
C1—C21.405 (3)C16—H160.9500
C2—C31.380 (4)C17—C181.400 (4)
C2—H20.9500C17—C201.477 (4)
C3—C41.400 (3)C18—C191.383 (4)
C3—H30.9500C18—H180.9500
C4—C51.408 (4)C19—H190.9500
C4—C71.481 (4)C20—N71.298 (3)
C5—C61.372 (4)C20—C211.503 (4)
C5—H50.9500C21—H21A0.9800
C6—H60.9500C21—H21B0.9800
C7—N21.300 (3)C21—H21C0.9800
C7—C81.509 (4)C22—O21.232 (3)
C8—H8A0.9800C22—N81.336 (3)
C8—H8B0.9800C22—C231.493 (4)
C8—H8C0.9800C23—N91.337 (3)
C9—O11.228 (3)C23—C241.385 (4)
C9—N31.353 (3)C24—N101.337 (3)
C9—C101.493 (4)C24—H240.9500
C10—N41.348 (3)C25—N101.334 (3)
C10—C111.383 (4)C25—C261.388 (4)
C11—N51.345 (3)C25—H250.9500
C11—H110.9500C26—N91.345 (3)
C12—N51.331 (3)C26—H260.9500
C12—C131.395 (4)N1—H1A0.88 (3)
C12—H120.9500N1—H1B0.97 (3)
C13—N41.329 (3)N2—N31.379 (3)
C13—H130.9500N3—H3A0.90 (3)
C14—N61.394 (4)N6—H6A0.91 (3)
C14—C191.396 (4)N6—H6B0.95 (3)
C14—C151.398 (4)N7—N81.387 (3)
C15—C161.384 (4)N8—H80.88 (3)
N1—C1—C6120.2 (2)C16—C17—C18117.0 (2)
N1—C1—C2122.1 (3)C16—C17—C20121.7 (2)
C6—C1—C2117.6 (2)C18—C17—C20121.3 (3)
C3—C2—C1120.8 (3)C19—C18—C17121.8 (3)
C3—C2—H2119.6C19—C18—H18119.1
C1—C2—H2119.6C17—C18—H18119.1
C2—C3—C4121.7 (2)C18—C19—C14120.6 (3)
C2—C3—H3119.1C18—C19—H19119.7
C4—C3—H3119.1C14—C19—H19119.7
C3—C4—C5117.1 (2)N7—C20—C17116.3 (2)
C3—C4—C7122.4 (2)N7—C20—C21123.2 (2)
C5—C4—C7120.5 (2)C17—C20—C21120.5 (2)
C6—C5—C4121.4 (3)C20—C21—H21A109.5
C6—C5—H5119.3C20—C21—H21B109.5
C4—C5—H5119.3H21A—C21—H21B109.5
C5—C6—C1121.3 (3)C20—C21—H21C109.5
C5—C6—H6119.3H21A—C21—H21C109.5
C1—C6—H6119.3H21B—C21—H21C109.5
N2—C7—C4115.2 (2)O2—C22—N8125.4 (3)
N2—C7—C8125.0 (2)O2—C22—C23121.2 (3)
C4—C7—C8119.8 (2)N8—C22—C23113.5 (2)
C7—C8—H8A109.5N9—C23—C24121.7 (2)
C7—C8—H8B109.5N9—C23—C22117.6 (2)
H8A—C8—H8B109.5C24—C23—C22120.7 (2)
C7—C8—H8C109.5N10—C24—C23122.7 (3)
H8A—C8—H8C109.5N10—C24—H24118.7
H8B—C8—H8C109.5C23—C24—H24118.7
O1—C9—N3124.3 (3)N10—C25—C26122.6 (3)
O1—C9—C10121.0 (2)N10—C25—H25118.7
N3—C9—C10114.7 (2)C26—C25—H25118.7
N4—C10—C11121.8 (2)N9—C26—C25121.5 (2)
N4—C10—C9117.7 (2)N9—C26—H26119.3
C11—C10—C9120.5 (2)C25—C26—H26119.3
N5—C11—C10122.7 (3)C1—N1—H1A121 (2)
N5—C11—H11118.6C1—N1—H1B114.9 (18)
C10—C11—H11118.6H1A—N1—H1B120 (3)
N5—C12—C13122.9 (3)C7—N2—N3117.9 (2)
N5—C12—H12118.5C9—N3—N2119.2 (2)
C13—C12—H12118.5C9—N3—H3A115.6 (17)
N4—C13—C12121.9 (3)N2—N3—H3A125.0 (17)
N4—C13—H13119.1C13—N4—C10115.8 (2)
C12—C13—H13119.1C12—N5—C11114.9 (2)
N6—C14—C19120.8 (3)C14—N6—H6A114.6 (19)
N6—C14—C15120.9 (3)C14—N6—H6B113.5 (18)
C19—C14—C15118.3 (2)H6A—N6—H6B114 (3)
C16—C15—C14120.6 (3)C20—N7—N8115.4 (2)
C16—C15—H15119.7C22—N8—N7121.9 (2)
C14—C15—H15119.7C22—N8—H8117.4 (18)
C15—C16—C17121.7 (3)N7—N8—H8119.9 (18)
C15—C16—H16119.1C23—N9—C26116.1 (2)
C17—C16—H16119.1C25—N10—C24115.4 (2)
N1—C1—C2—C3176.4 (2)C16—C17—C20—N7160.7 (2)
C6—C1—C2—C3−0.7 (4)C18—C17—C20—N7−17.4 (4)
C1—C2—C3—C4−0.1 (4)C16—C17—C20—C21−20.8 (4)
C2—C3—C4—C50.1 (4)C18—C17—C20—C21161.1 (3)
C2—C3—C4—C7−179.7 (2)O2—C22—C23—N9−177.7 (2)
C3—C4—C5—C60.8 (4)N8—C22—C23—N94.0 (3)
C7—C4—C5—C6−179.4 (2)O2—C22—C23—C242.5 (4)
C4—C5—C6—C1−1.6 (4)N8—C22—C23—C24−175.9 (2)
N1—C1—C6—C5−175.7 (2)N9—C23—C24—N100.0 (4)
C2—C1—C6—C51.5 (4)C22—C23—C24—N10179.8 (2)
C3—C4—C7—N2−176.1 (2)N10—C25—C26—N9−0.1 (4)
C5—C4—C7—N24.2 (3)C4—C7—N2—N3179.6 (2)
C3—C4—C7—C84.9 (4)C8—C7—N2—N3−1.4 (4)
C5—C4—C7—C8−174.9 (2)O1—C9—N3—N2−0.1 (4)
O1—C9—C10—N4178.8 (2)C10—C9—N3—N2178.5 (2)
N3—C9—C10—N40.1 (3)C7—N2—N3—C9176.7 (2)
O1—C9—C10—C110.0 (4)C12—C13—N4—C100.2 (4)
N3—C9—C10—C11−178.6 (2)C11—C10—N4—C13−0.3 (4)
N4—C10—C11—N50.0 (4)C9—C10—N4—C13−179.0 (2)
C9—C10—C11—N5178.7 (2)C13—C12—N5—C11−0.3 (4)
N5—C12—C13—N40.1 (4)C10—C11—N5—C120.3 (4)
N6—C14—C15—C16−178.0 (2)C17—C20—N7—N8−179.4 (2)
C19—C14—C15—C161.1 (4)C21—C20—N7—N82.1 (4)
C14—C15—C16—C17−1.2 (4)O2—C22—N8—N74.3 (4)
C15—C16—C17—C180.7 (4)C23—C22—N8—N7−177.4 (2)
C15—C16—C17—C20−177.5 (2)C20—N7—N8—C22−172.7 (2)
C16—C17—C18—C19−0.1 (4)C24—C23—N9—C26−0.9 (4)
C20—C17—C18—C19178.1 (2)C22—C23—N9—C26179.2 (2)
C17—C18—C19—C140.1 (4)C25—C26—N9—C231.0 (4)
N6—C14—C19—C18178.5 (2)C26—C25—N10—C24−0.9 (4)
C15—C14—C19—C18−0.6 (4)C23—C24—N10—C250.9 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···N10i0.88 (3)2.16 (3)3.030 (4)170 (3)
N1—H1B···O2ii0.97 (3)1.89 (3)2.852 (3)171 (3)
N6—H6A···N1iii0.91 (3)2.38 (3)3.162 (4)145 (3)
N6—H6B···O1ii0.95 (3)2.07 (3)3.015 (3)169 (3)

Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2638).

References

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