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The title compound, C13H14N4O, has been synthesized as an ADDA (D: hydrogen-bond donor; A: hydrogen-bond acceptor) recognition unit for quadruple hydrogen bonds. In the solid state, it crystallizes as a centrosymmetric dimer connecting one N-H group with one pyridyl N atom. Furthermore, an intramolecular hydrogen bond is formed connecting two N atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801007334/na6071sup1.cif
Contains datablocks lue5, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801007334/na6071Isup2.hkl
Contains datablock I

CCDC reference: 170295

Key indicators

  • Single-crystal X-ray study
  • T = 133 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.094
  • Data-to-parameter ratio = 15.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1991).

(lue5) top
Crystal data top
C13H14N4OF(000) = 512
Mr = 242.28Dx = 1.248 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.1142 (2) ÅCell parameters from 6371 reflections
b = 11.0127 (3) Åθ = 1.0–25.0°
c = 16.4630 (4) ŵ = 0.08 mm1
β = 90.078 (1)°T = 133 K
V = 1289.82 (6) Å3Block, colourless
Z = 40.50 × 0.30 × 0.20 mm
Data collection top
Siemens CCD three-circle
diffractometer
2629 independent reflections
Radiation source: fine-focus sealed tube2240 reflections with I > 2σ(I)
Highly oriented graphite crystal monochromatorRint = 0.028
ω scansθmax = 26.3°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements)
'SADABS (Sheldrick, 1996)'
h = 88
Tmin = 0.960, Tmax = 0.984k = 1313
23905 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0446P)2 + 0.3616P]
where P = (Fo2 + 2Fc2)/3
2629 reflections(Δ/σ)max = 0.001
173 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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) top
xyzUiso*/Ueq
N10.21514 (14)0.59679 (9)0.49618 (6)0.0237 (2)
H10.103 (2)0.5843 (14)0.5224 (9)0.040 (4)*
C20.24808 (15)0.51472 (10)0.43411 (7)0.0212 (2)
O20.13024 (11)0.43464 (8)0.41927 (5)0.0268 (2)
N30.41201 (14)0.52965 (9)0.39267 (6)0.0217 (2)
H30.487 (2)0.5872 (14)0.4103 (9)0.034 (4)*
C110.32076 (16)0.69639 (10)0.52357 (7)0.0212 (2)
N120.48814 (13)0.71846 (9)0.48957 (6)0.0221 (2)
C130.58920 (17)0.81542 (11)0.51587 (7)0.0244 (3)
C13'0.77567 (17)0.83441 (12)0.47475 (8)0.0321 (3)
H13A0.85060.76000.47880.048*
H13B0.84280.90130.50130.048*
H13C0.75500.85440.41740.048*
C140.52281 (18)0.89154 (11)0.57654 (8)0.0291 (3)
H140.59470.95960.59370.035*
C150.34913 (18)0.86673 (12)0.61205 (8)0.0295 (3)
H150.30260.91740.65410.035*
C160.24496 (17)0.76839 (11)0.58593 (7)0.0253 (3)
H160.12630.75010.60930.030*
C310.48264 (15)0.46026 (10)0.32803 (7)0.0205 (2)
N320.65170 (13)0.50075 (9)0.30376 (6)0.0225 (2)
C330.73843 (17)0.44228 (11)0.24248 (7)0.0258 (3)
C33'0.92571 (18)0.49386 (14)0.21721 (8)0.0362 (3)
H33A1.00770.50080.26490.054*
H33B0.90710.57440.19310.054*
H33C0.98420.44000.17720.054*
C340.65752 (18)0.34201 (12)0.20396 (7)0.0291 (3)
H340.72170.30160.16120.035*
C350.48189 (18)0.30239 (11)0.22920 (7)0.0284 (3)
H350.42440.23480.20330.034*
C360.39009 (17)0.36147 (11)0.29223 (7)0.0242 (3)
H360.26960.33600.31030.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0198 (5)0.0254 (5)0.0260 (5)0.0033 (4)0.0062 (4)0.0035 (4)
C20.0199 (5)0.0207 (6)0.0230 (6)0.0010 (4)0.0008 (4)0.0014 (4)
O20.0218 (4)0.0273 (5)0.0313 (5)0.0053 (3)0.0051 (3)0.0050 (4)
N30.0209 (5)0.0194 (5)0.0249 (5)0.0028 (4)0.0046 (4)0.0027 (4)
C110.0222 (6)0.0203 (6)0.0212 (6)0.0013 (4)0.0007 (4)0.0018 (4)
N120.0219 (5)0.0212 (5)0.0232 (5)0.0010 (4)0.0006 (4)0.0018 (4)
C130.0266 (6)0.0212 (6)0.0254 (6)0.0021 (5)0.0047 (5)0.0047 (5)
C13'0.0278 (6)0.0292 (7)0.0392 (7)0.0079 (5)0.0014 (5)0.0031 (6)
C140.0354 (7)0.0217 (6)0.0300 (6)0.0025 (5)0.0075 (5)0.0006 (5)
C150.0373 (7)0.0255 (6)0.0256 (6)0.0061 (5)0.0020 (5)0.0042 (5)
C160.0249 (6)0.0263 (6)0.0249 (6)0.0040 (5)0.0016 (5)0.0003 (5)
C310.0220 (6)0.0187 (6)0.0209 (5)0.0035 (4)0.0019 (4)0.0030 (4)
N320.0221 (5)0.0224 (5)0.0229 (5)0.0023 (4)0.0031 (4)0.0034 (4)
C330.0264 (6)0.0289 (6)0.0222 (6)0.0064 (5)0.0037 (5)0.0044 (5)
C33'0.0281 (7)0.0479 (9)0.0326 (7)0.0021 (6)0.0107 (5)0.0005 (6)
C340.0377 (7)0.0277 (6)0.0220 (6)0.0084 (5)0.0053 (5)0.0008 (5)
C350.0386 (7)0.0208 (6)0.0258 (6)0.0024 (5)0.0008 (5)0.0010 (5)
C360.0262 (6)0.0206 (6)0.0259 (6)0.0003 (5)0.0015 (5)0.0016 (5)
Geometric parameters (Å, º) top
N1—C21.3843 (15)C15—C161.3806 (18)
N1—C111.4036 (15)C15—H150.9500
N1—H10.920 (17)C16—H160.9500
C2—O21.2409 (14)C31—N321.3440 (15)
C2—N31.3618 (15)C31—C361.4012 (16)
N3—C311.4036 (15)N32—C331.3471 (15)
N3—H30.879 (16)C33—C341.3972 (18)
C11—N121.3387 (15)C33—C33'1.5075 (18)
C11—C161.4054 (16)C33'—H33A0.9800
N12—C131.3578 (15)C33'—H33B0.9800
C13—C141.3873 (18)C33'—H33C0.9800
C13—C13'1.5048 (17)C34—C351.3877 (18)
C13'—H13A0.9800C34—H340.9500
C13'—H13B0.9800C35—C361.3887 (17)
C13'—H13C0.9800C35—H350.9500
C14—C151.3946 (19)C36—H360.9500
C14—H140.9500
C2—N1—C11131.01 (10)C14—C15—H15120.0
C2—N1—H1113.4 (10)C15—C16—C11117.63 (11)
C11—N1—H1115.6 (10)C15—C16—H16121.2
O2—C2—N3124.47 (11)C11—C16—H16121.2
O2—C2—N1119.62 (10)N32—C31—C36123.55 (10)
N3—C2—N1115.91 (10)N32—C31—N3111.48 (10)
C2—N3—C31128.45 (10)C36—C31—N3124.97 (10)
C2—N3—H3116.3 (10)C31—N32—C33118.36 (10)
C31—N3—H3115.1 (10)N32—C33—C34121.93 (11)
N12—C11—N1118.93 (10)N32—C33—C33'115.63 (11)
N12—C11—C16123.05 (11)C34—C33—C33'122.43 (11)
N1—C11—C16118.02 (10)C33—C33'—H33A109.5
C11—N12—C13118.70 (10)C33—C33'—H33B109.5
N12—C13—C14121.61 (11)H33A—C33'—H33B109.5
N12—C13—C13'115.63 (11)C33—C33'—H33C109.5
C14—C13—C13'122.76 (11)H33A—C33'—H33C109.5
C13—C13'—H13A109.5H33B—C33'—H33C109.5
C13—C13'—H13B109.5C35—C34—C33118.89 (11)
H13A—C13'—H13B109.5C35—C34—H34120.6
C13—C13'—H13C109.5C33—C34—H34120.6
H13A—C13'—H13C109.5C34—C35—C36120.06 (12)
H13B—C13'—H13C109.5C34—C35—H35120.0
C13—C14—C15119.08 (11)C36—C35—H35120.0
C13—C14—H14120.5C35—C36—C31117.19 (11)
C15—C14—H14120.5C35—C36—H36121.4
C16—C15—C14119.91 (12)C31—C36—H36121.4
C16—C15—H15120.0
C11—N1—C2—O2177.96 (11)N12—C11—C16—C150.62 (17)
C11—N1—C2—N31.58 (18)N1—C11—C16—C15179.50 (10)
O2—C2—N3—C311.10 (19)C2—N3—C31—N32178.54 (10)
N1—C2—N3—C31179.39 (10)C2—N3—C31—C361.83 (19)
C2—N1—C11—N123.77 (18)C36—C31—N32—C330.99 (16)
C2—N1—C11—C16176.34 (11)N3—C31—N32—C33179.37 (10)
N1—C11—N12—C13179.54 (10)C31—N32—C33—C340.15 (17)
C16—C11—N12—C130.58 (16)C31—N32—C33—C33'178.84 (10)
C11—N12—C13—C140.19 (16)N32—C33—C34—C350.60 (18)
C11—N12—C13—C13'179.94 (10)C33'—C33—C34—C35178.00 (12)
N12—C13—C14—C150.88 (18)C33—C34—C35—C360.55 (18)
C13'—C13—C14—C15179.38 (11)C34—C35—C36—C310.21 (17)
C13—C14—C15—C160.82 (18)N32—C31—C36—C351.02 (17)
C14—C15—C16—C110.11 (17)N3—C31—C36—C35179.39 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.920 (17)1.928 (17)2.8468 (13)177.0 (15)
N3—H3···N120.879 (16)1.948 (16)2.6757 (14)139.3 (13)
Symmetry code: (i) x, y+1, z+1.
 

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