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The reaction of 5-methyl-2-phenyl-2H-1,2,4-triazol-3(4H)-one, benzaldehyde and malononitrile in ethanol in the presence of triethyl­amine produced the title compound, C10H8N2, rather than the anti­cipated polysubstituted 2,6-dicyano­aniline. The plane defined by the phenyl ipso-C atom, the methyl­ene C atom and the central C atom of the malononitrile group is roughly orthogonal to the benzene ring plane [dihedral angle = 81.6 (2)°]; one of the nitrile groups of the malononitrile almost lies in this plane [corresponding C(Ph)-CH2-C-CN torsion angle = 176.06 (17)°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045235/ya2029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045235/ya2029Isup2.hkl
Contains datablock I

CCDC reference: 630537

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.055
  • wR factor = 0.174
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level B ABSMU01_ALERT_1_B The ratio of given/expected absorption coefficient lies outside the range 0.95 <> 1.05 Calculated value of mu = 0.074 Value of mu given = 0.070
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 6.32 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

2-benzylmalononitrile top
Crystal data top
C10H8N2F(000) = 328
Mr = 156.18Dx = 1.212 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 997 reflections
a = 5.8391 (13) Åθ = 2.7–20.3°
b = 15.145 (4) ŵ = 0.07 mm1
c = 9.807 (2) ÅT = 292 K
β = 99.270 (5)°Block, colourless
V = 856.0 (3) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1942 independent reflections
Radiation source: fine-focus sealed tube1061 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.099
φ and ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.978, Tmax = 0.985k = 1919
6068 measured reflectionsl = 1212
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0839P)2]
where P = (Fo2 + 2Fc2)/3
1942 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.16 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
C10.0426 (4)0.68694 (13)0.0775 (2)0.0559 (6)
H10.12430.72240.13050.067*
C20.1401 (4)0.66421 (15)0.0560 (2)0.0640 (7)
H20.28780.68430.09230.077*
C30.0205 (4)0.61221 (15)0.1353 (2)0.0655 (7)
H30.08580.59770.22530.079*
C40.1934 (4)0.58240 (14)0.0811 (3)0.0663 (7)
H40.27490.54680.13400.080*
C50.2907 (4)0.60432 (14)0.0513 (2)0.0575 (6)
H50.43750.58290.08670.069*
C60.1785 (3)0.65647 (12)0.1322 (2)0.0447 (5)
C70.2869 (4)0.67868 (12)0.2781 (2)0.0510 (6)
H7A0.21600.73200.30690.061*
H7B0.45100.69020.28080.061*
C80.2571 (3)0.60324 (13)0.3802 (2)0.0473 (5)
H80.32690.54970.34860.057*
C90.3780 (4)0.62392 (14)0.5200 (2)0.0577 (6)
C100.0110 (4)0.58525 (13)0.3825 (2)0.0519 (6)
N10.4762 (4)0.64159 (15)0.6253 (2)0.0840 (7)
N20.1830 (4)0.57203 (14)0.3813 (2)0.0733 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0450 (13)0.0617 (13)0.0594 (14)0.0089 (10)0.0029 (11)0.0052 (11)
C20.0464 (14)0.0728 (15)0.0659 (16)0.0005 (11)0.0119 (12)0.0165 (13)
C30.0779 (18)0.0607 (14)0.0511 (15)0.0108 (12)0.0098 (13)0.0061 (11)
C40.0803 (18)0.0600 (14)0.0579 (15)0.0101 (12)0.0089 (13)0.0027 (11)
C50.0491 (13)0.0627 (14)0.0574 (15)0.0102 (10)0.0017 (11)0.0046 (11)
C60.0401 (11)0.0422 (11)0.0496 (12)0.0034 (8)0.0005 (9)0.0047 (9)
C70.0464 (12)0.0498 (11)0.0534 (13)0.0030 (9)0.0026 (10)0.0009 (9)
C80.0440 (12)0.0491 (11)0.0448 (12)0.0031 (9)0.0047 (9)0.0022 (9)
C90.0537 (14)0.0632 (14)0.0529 (15)0.0037 (10)0.0016 (12)0.0024 (11)
C100.0501 (14)0.0544 (13)0.0487 (13)0.0043 (10)0.0007 (10)0.0026 (9)
N10.0782 (16)0.1093 (18)0.0562 (14)0.0035 (12)0.0140 (12)0.0091 (12)
N20.0508 (13)0.0865 (15)0.0809 (15)0.0033 (10)0.0056 (11)0.0059 (11)
Geometric parameters (Å, º) top
C1—C21.385 (3)C5—H50.9300
C1—C61.395 (3)C6—C71.506 (3)
C1—H10.9300C7—C81.548 (3)
C2—C31.374 (3)C7—H7A0.9700
C2—H20.9300C7—H7B0.9700
C3—C41.354 (3)C8—C101.466 (3)
C3—H30.9300C8—C91.471 (3)
C4—C51.371 (3)C8—H80.9800
C4—H40.9300C9—N11.129 (3)
C5—C61.360 (3)C10—N21.149 (3)
C2—C1—C6119.7 (2)C5—C6—C7121.05 (18)
C2—C1—H1120.2C1—C6—C7120.83 (19)
C6—C1—H1120.2C6—C7—C8112.10 (16)
C3—C2—C1120.6 (2)C6—C7—H7A109.2
C3—C2—H2119.7C8—C7—H7A109.2
C1—C2—H2119.7C6—C7—H7B109.2
C4—C3—C2119.3 (2)C8—C7—H7B109.2
C4—C3—H3120.3H7A—C7—H7B107.9
C2—C3—H3120.3C10—C8—C9110.49 (16)
C3—C4—C5120.4 (2)C10—C8—C7111.07 (16)
C3—C4—H4119.8C9—C8—C7111.04 (16)
C5—C4—H4119.8C10—C8—H8108.0
C6—C5—C4121.9 (2)C9—C8—H8108.0
C6—C5—H5119.1C7—C8—H8108.0
C4—C5—H5119.1N1—C9—C8177.5 (2)
C5—C6—C1118.10 (19)N2—C10—C8178.4 (2)
C6—C1—C2—C30.3 (3)C2—C1—C6—C50.5 (3)
C1—C2—C3—C40.7 (3)C2—C1—C6—C7178.79 (18)
C2—C3—C4—C50.5 (3)C5—C6—C7—C880.6 (2)
C3—C4—C5—C60.3 (3)C1—C6—C7—C897.7 (2)
C4—C5—C6—C10.8 (3)C6—C7—C8—C1060.5 (2)
C4—C5—C6—C7179.07 (19)C6—C7—C8—C9176.09 (16)
 

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