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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o560-o561
https://doi.org/10.1107/S2056989015012608

Crystal structure of 2-[2-(benz­yl­oxy)benzyl­­idene]malono­nitrile

Sammer Yousuf,a* Huma Bano,a Munira Taj Muhammada and Khalid Mohammed Khana

aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: dr.sammer.yousuf@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 June 2015; accepted 30 June 2015; online 8 July 2015)

In the title benzyl­idenemalono­nitrile derivative, C17H12N2O, the dihedral angles between the central benzene ring and the Y-shaped C=C(CN)2 group (r.m.s. deviation = 0.006 Å) and the terminal benzene ring are 12.72 (8) and 37.60 (11)°, respectively. The Car—O—Csp3—Car torsion angle is −174.52 (13)° and the major twist between the aromatic rings occurs about the Csp3—Car bond. Weak aromatic π–π stacking [centroid–centroid separation = 3.7784 (13) Å; slippage = 1.21 Å] between inversion-related pairs of the central benzene rings is observed in the crystal.

CCDC reference: 1409734

Similar articles

1. Related literature

For the applications and biological activities of benzyl­idenemalono­nitrile derivatives, see: Turpaev et al. (2011[Turpaev, K., Ermolenko, M., Cresteil, T. & Drapier, J. C. (2011). Biochem. Pharmacol. 82, 535-547.]); Sagara et al. (2002[Sagara, Y., Ishige, K., Tsai, C. & Maher, P. (2002). J. Biol. Chem. 277, 36204-36215.]); Novogrodsky et al. (1994[Novogrodsky, A., Vanichkin, A., Patya, M., Gazit, A., Osherov, N. & Levitzki, A. (1994). Science, 264, 1319-1322.]); Gazit et al. (1989[Gazit, A., Yaish, P., Gilon, C. & Levitzki, A. (1989). J. Med. Chem. 32, 2344-2352.]). For the crystal structure of a related compound, see: Gan et al. (2012[Gan, H., Liu, X., Fang, Z. & Guo, K. (2012). Acta Cryst. E68, o1690.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C17H12N2O

  • Mr = 260.29

  • Triclinic, [P \overline 1]

  • a = 7.2959 (9) Å

  • b = 9.4963 (12) Å

  • c = 11.0280 (14) Å

  • α = 97.709 (3)°

  • β = 107.953 (3)°

  • γ = 105.155 (3)°

  • V = 682.13 (15) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.34 × 0.11 × 0.07 mm

2.2. Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.994

  • 7776 measured reflections

  • 2545 independent reflections

  • 1722 reflections with I > 2σ(I)

  • Rint = 0.032

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.112

  • S = 1.01

  • 2545 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.11 e Å−3

  • Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1409734

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015012608/hb7442sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012608/hb7442Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015012608/hb7442Isup3.cml

checkCIF report


Comment top

Malononitriles and their benzylidene derivative represent a wide group of organic compounds having a number of pharmacological activities including inhibition of epidermal growth factor protein tyrosine kinas (Turpaev et al., 2011, Gazit et al., 1989), expression of iNOS and COX-2 pro-inflammatory agents. Structural analogues of benzylidenemalononitrile are also known to have free radical scavenging (Sagara et al., 2002) and antiinflammatory properties (suppression of TNFα release) (Novogrodsky et al., 1994). The title compound was obtained as a part of our ongoing resaerch to synthesize and evaluate the biological activities of structural analogues having benzylidenemalononitrile as basic nucleus.

The structure of title compound is similar to that of previously published 2-[4-(benzyloxy)benzylidene]malononitrile (Gan et al., 2012) with the difference that the benzyloxy (O1/C1–C7) group found to be attached at ortho position on benzylidenemalononitrile (N1/N2/C8–C16) moiety (Fig. 1) in contrast to para position, as observed in previously published 2-[4-(Benzyloxy)benzylidene]malononitrile. The dihedral angles between two planner phenyl rings phenyl(C1–C6)and (C8–C13) is 37.60 (11)°. Dicyanoethylene (N1–N2/C14–C17) group found to be coplanar with the benzene ring (C8–C13) to which it is attached. The bond lengths and angle were found to be similar as in structurally related 2-[4-(benzyloxy)benzylidene]malononitrile (Gan et al., 2012).

Related literature top

For the applications and biological activities of benzylidenemalononitrile derivatives, see: Turpaev et al. (2011); Sagara et al. (2002); Novogrodsky et al. (1994); Gazit et al. (1989). For the crystal structure of a related compound, see: Gan et al. (2012).

Experimental top

In a round-bottomed flask 2-benzyloxybenzaldehyde (1 mmol) and a catalytic amount (3 mol%) of Bi(NO3)3 in water/ethanol (10 ml) were stirred for 2 minutes at room temperature followed by the additon of malononitrile (1.1 mmol). The reaction mixture was refluxed for 20 minutes. After completion of the reaction (TLC analysis), Bi(NO3)3 was filtered for the next use and the filtrate was kept at room temperature over night to obtain crystals. Crystals were filtered, washed with water, dried, and re-crystallized from hot ethanol as colourless plates. Thin layer chromatography was carried out on aluminium plates pre-coated with silica gel (Kieselgel 60, E. Merck, Darmstadt, Germany). UV light at 254 and 365 nm was used for chromatograms visualization.

Refinement top

H atoms on phenyl and methine were positioned geometrically with C—H = 0.93 Å (CH phenyl) and 0.97 Å (CH) and constrained to ride on their parent atoms with Uiso(H)=1.2Ueq(CH).

Structure description top

Malononitriles and their benzylidene derivative represent a wide group of organic compounds having a number of pharmacological activities including inhibition of epidermal growth factor protein tyrosine kinas (Turpaev et al., 2011, Gazit et al., 1989), expression of iNOS and COX-2 pro-inflammatory agents. Structural analogues of benzylidenemalononitrile are also known to have free radical scavenging (Sagara et al., 2002) and antiinflammatory properties (suppression of TNFα release) (Novogrodsky et al., 1994). The title compound was obtained as a part of our ongoing resaerch to synthesize and evaluate the biological activities of structural analogues having benzylidenemalononitrile as basic nucleus.

The structure of title compound is similar to that of previously published 2-[4-(benzyloxy)benzylidene]malononitrile (Gan et al., 2012) with the difference that the benzyloxy (O1/C1–C7) group found to be attached at ortho position on benzylidenemalononitrile (N1/N2/C8–C16) moiety (Fig. 1) in contrast to para position, as observed in previously published 2-[4-(Benzyloxy)benzylidene]malononitrile. The dihedral angles between two planner phenyl rings phenyl(C1–C6)and (C8–C13) is 37.60 (11)°. Dicyanoethylene (N1–N2/C14–C17) group found to be coplanar with the benzene ring (C8–C13) to which it is attached. The bond lengths and angle were found to be similar as in structurally related 2-[4-(benzyloxy)benzylidene]malononitrile (Gan et al., 2012).

For the applications and biological activities of benzylidenemalononitrile derivatives, see: Turpaev et al. (2011); Sagara et al. (2002); Novogrodsky et al. (1994); Gazit et al. (1989). For the crystal structure of a related compound, see: Gan et al. (2012).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound (I).
2-{[2-(Benzyloxy)phenyl]methylidene}propanedinitrile top
Crystal data top
C17H12N2OZ = 2
Mr = 260.29F(000) = 272
Triclinic, P1Dx = 1.267 Mg m−3
a = 7.2959 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.4963 (12) ÅCell parameters from 1299 reflections
c = 11.0280 (14) Åθ = 2.3–20.8°
α = 97.709 (3)°µ = 0.08 mm−1
β = 107.953 (3)°T = 293 K
γ = 105.155 (3)°Plate, colourless
V = 682.13 (15) Å30.34 × 0.11 × 0.07 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		2545 independent reflections
Radiation source: fine-focus sealed tube1722 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scanθmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −8→8
Tmin = 0.973, Tmax = 0.994k = −11→11
7776 measured reflectionsl = −13→13
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0495P)2 + 0.016P]
where P = (Fo2 + 2Fc2)/3
2545 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.11 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C17H12N2Oγ = 105.155 (3)°
Mr = 260.29V = 682.13 (15) Å3
Triclinic, P1Z = 2
a = 7.2959 (9) ÅMo Kα radiation
b = 9.4963 (12) ŵ = 0.08 mm−1
c = 11.0280 (14) ÅT = 293 K
α = 97.709 (3)°0.34 × 0.11 × 0.07 mm
β = 107.953 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer		2545 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1722 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.994Rint = 0.032
7776 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.01Δρmax = 0.11 e Å−3
2545 reflectionsΔρmin = −0.17 e Å−3
181 parameters
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
O10.37248 (18)0.70351 (12)0.15139 (10)0.0558 (3)
N1−0.0533 (3)0.06530 (19)0.15041 (17)0.0861 (6)
N20.2682 (3)0.38995 (18)0.52272 (16)0.0799 (6)
C10.6578 (3)0.9358 (2)0.36642 (19)0.0682 (6)
H1A0.67040.84090.36660.082*
C20.7541 (3)1.0476 (3)0.4799 (2)0.0840 (7)
H2A0.83001.02760.55650.101*
C30.7382 (4)1.1883 (3)0.4800 (2)0.0864 (7)
H3A0.80361.26390.55650.104*
C40.6260 (3)1.2171 (2)0.3675 (2)0.0816 (7)
H4A0.61631.31270.36700.098*
C50.5273 (3)1.1043 (2)0.2549 (2)0.0653 (5)
H5A0.44871.12410.17920.078*
C60.5432 (3)0.96316 (18)0.25284 (17)0.0501 (4)
C70.4489 (3)0.84695 (18)0.12655 (17)0.0573 (5)
H7A0.33880.87080.06660.069*
H7B0.54950.84530.08630.069*
C80.2956 (2)0.57991 (18)0.05089 (15)0.0459 (4)
C90.2793 (3)0.5848 (2)−0.07670 (16)0.0545 (5)
H9A0.32180.6764−0.09780.065*
C100.2002 (3)0.4537 (2)−0.17214 (17)0.0607 (5)
H10A0.19020.4575−0.25770.073*
C110.1356 (3)0.3172 (2)−0.14330 (17)0.0609 (5)
H11A0.08240.2293−0.20880.073*
C120.1501 (3)0.31157 (19)−0.01748 (16)0.0539 (5)
H12A0.10610.21890.00160.065*
C130.2296 (2)0.44161 (17)0.08304 (15)0.0440 (4)
C140.2524 (2)0.44280 (18)0.21768 (15)0.0478 (4)
H14A0.33150.53430.27650.057*
C150.1784 (2)0.33340 (18)0.27265 (15)0.0473 (4)
C160.0496 (3)0.1845 (2)0.20382 (17)0.0568 (5)
C170.2273 (3)0.36414 (19)0.41193 (19)0.0569 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0745 (8)0.0390 (7)0.0461 (7)0.0046 (6)0.0232 (6)0.0091 (5)
N10.1044 (15)0.0552 (11)0.0784 (12)−0.0080 (10)0.0388 (11)0.0033 (9)
N20.1137 (15)0.0664 (11)0.0508 (11)0.0125 (10)0.0309 (10)0.0144 (9)
C10.0809 (14)0.0509 (12)0.0639 (13)0.0202 (10)0.0152 (11)0.0126 (10)
C20.0897 (17)0.0751 (16)0.0632 (14)0.0207 (13)0.0055 (12)0.0023 (12)
C30.0827 (16)0.0622 (15)0.0862 (17)0.0083 (12)0.0189 (13)−0.0159 (12)
C40.0847 (16)0.0464 (12)0.1071 (19)0.0192 (11)0.0332 (14)0.0030 (13)
C50.0673 (13)0.0491 (12)0.0790 (14)0.0183 (10)0.0248 (11)0.0177 (10)
C60.0521 (10)0.0404 (10)0.0562 (11)0.0086 (8)0.0221 (9)0.0121 (8)
C70.0675 (12)0.0448 (10)0.0564 (11)0.0114 (9)0.0205 (9)0.0190 (9)
C80.0448 (10)0.0475 (10)0.0404 (9)0.0099 (8)0.0146 (8)0.0060 (8)
C90.0587 (11)0.0578 (11)0.0459 (10)0.0130 (9)0.0207 (9)0.0156 (9)
C100.0634 (12)0.0778 (14)0.0382 (10)0.0178 (10)0.0198 (9)0.0113 (10)
C110.0663 (12)0.0603 (12)0.0443 (11)0.0099 (10)0.0189 (9)−0.0025 (9)
C120.0577 (11)0.0464 (10)0.0484 (11)0.0070 (9)0.0179 (9)0.0039 (8)
C130.0444 (9)0.0430 (9)0.0389 (9)0.0090 (7)0.0128 (7)0.0066 (7)
C140.0526 (10)0.0394 (9)0.0424 (10)0.0084 (8)0.0124 (8)0.0044 (7)
C150.0540 (10)0.0416 (10)0.0410 (9)0.0092 (8)0.0163 (8)0.0068 (8)
C160.0674 (12)0.0461 (11)0.0522 (11)0.0064 (10)0.0250 (9)0.0108 (9)
C170.0716 (13)0.0442 (11)0.0508 (12)0.0083 (9)0.0242 (10)0.0123 (9)
Geometric parameters (Å, º) top
O1—C81.3580 (18)C7—H7B0.9700
O1—C71.4277 (18)C8—C91.383 (2)
N1—C161.138 (2)C8—C131.408 (2)
N2—C171.140 (2)C9—C101.374 (2)
C1—C61.375 (2)C9—H9A0.9300
C1—C21.378 (3)C10—C111.374 (2)
C1—H1A0.9300C10—H10A0.9300
C2—C31.371 (3)C11—C121.368 (2)
C2—H2A0.9300C11—H11A0.9300
C3—C41.366 (3)C12—C131.397 (2)
C3—H3A0.9300C12—H12A0.9300
C4—C51.377 (3)C13—C141.440 (2)
C4—H4A0.9300C14—C151.348 (2)
C5—C61.373 (2)C14—H14A0.9300
C5—H5A0.9300C15—C161.427 (2)
C6—C71.494 (2)C15—C171.435 (2)
C7—H7A0.9700
C8—O1—C7118.82 (13)O1—C8—C13115.91 (14)
C6—C1—C2120.69 (18)C9—C8—C13120.32 (15)
C6—C1—H1A119.7C10—C9—C8119.76 (17)
C2—C1—H1A119.7C10—C9—H9A120.1
C3—C2—C1120.0 (2)C8—C9—H9A120.1
C3—C2—H2A120.0C9—C10—C11121.12 (16)
C1—C2—H2A120.0C9—C10—H10A119.4
C4—C3—C2119.8 (2)C11—C10—H10A119.4
C4—C3—H3A120.1C12—C11—C10119.45 (16)
C2—C3—H3A120.1C12—C11—H11A120.3
C3—C4—C5119.9 (2)C10—C11—H11A120.3
C3—C4—H4A120.0C11—C12—C13121.61 (16)
C5—C4—H4A120.0C11—C12—H12A119.2
C6—C5—C4121.0 (2)C13—C12—H12A119.2
C6—C5—H5A119.5C12—C13—C8117.74 (15)
C4—C5—H5A119.5C12—C13—C14124.20 (15)
C5—C6—C1118.55 (17)C8—C13—C14118.05 (14)
C5—C6—C7119.67 (17)C15—C14—C13130.76 (15)
C1—C6—C7121.64 (16)C15—C14—H14A114.6
O1—C7—C6109.28 (14)C13—C14—H14A114.6
O1—C7—H7A109.8C14—C15—C16125.63 (15)
C6—C7—H7A109.8C14—C15—C17119.51 (15)
O1—C7—H7B109.8C16—C15—C17114.86 (14)
C6—C7—H7B109.8N1—C16—C15179.11 (19)
H7A—C7—H7B108.3N2—C17—C15179.2 (2)
O1—C8—C9123.76 (15)
C6—C1—C2—C3−0.7 (3)C9—C10—C11—C120.1 (3)
C1—C2—C3—C40.2 (4)C10—C11—C12—C13−0.1 (3)
C2—C3—C4—C50.8 (4)C11—C12—C13—C8−0.3 (2)
C3—C4—C5—C6−1.4 (3)C11—C12—C13—C14−178.75 (16)
C4—C5—C6—C10.9 (3)O1—C8—C13—C12−179.77 (14)
C4—C5—C6—C7−174.84 (18)C9—C8—C13—C120.6 (2)
C2—C1—C6—C50.2 (3)O1—C8—C13—C14−1.2 (2)
C2—C1—C6—C7175.84 (19)C9—C8—C13—C14179.23 (15)
C8—O1—C7—C6−174.52 (13)C12—C13—C14—C15−12.2 (3)
C5—C6—C7—O1−144.67 (16)C8—C13—C14—C15169.29 (17)
C1—C6—C7—O139.7 (2)C13—C14—C15—C16−1.5 (3)
C7—O1—C8—C9−2.6 (2)C13—C14—C15—C17179.08 (17)
C7—O1—C8—C13177.82 (14)C14—C15—C16—N1−176 (100)
O1—C8—C9—C10179.76 (15)C17—C15—C16—N13 (14)
C13—C8—C9—C10−0.7 (2)C14—C15—C17—N2−22 (16)
C8—C9—C10—C110.3 (3)C16—C15—C17—N2159 (16)

Experimental details

Crystal data
Chemical formulaC17H12N2O
Mr260.29
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.2959 (9), 9.4963 (12), 11.0280 (14)
α, β, γ (°)97.709 (3), 107.953 (3), 105.155 (3)
V (Å3)682.13 (15)
Z2
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.34 × 0.11 × 0.07
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.973, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections		7776, 2545, 1722
Rint0.032
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.112, 1.01
No. of reflections2545
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.11, −0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors acknowledge the financial support of the Higher Education Commission of Pakistan (HEC)through research project No. 20–2073 20–2216 and under the National Research Program for Universities.

References

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ISSN: 2056-9890
Volume 71| Part 8| August 2015| Pages o560-o561
https://doi.org/10.1107/S2056989015012608
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