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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 67| Part 1| January 2011| Page o117
https://doi.org/10.1107/S1600536810051330

N,N′-Di­phenyl­but-2-enedi­amide

B. Thimme Gowda,a* Sabine Foro,b K. Shakuntalaa and Hartmut Fuessb

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 5 December 2010; accepted 7 December 2010; online 11 December 2010)

In the title compound, C16H14N2O2, the conformations of the N—H and C=O bonds in the C—NH—CO—CH =CH—CO—NH—C segment are anti to each other. The two C=O bonds are also anti to each other. The two phenyl rings make an inter­planar angle of 41.2 (1)°. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, inter­molecular N—H⋯O hydrogen bonding links the mol­ecules into infinite chains along the a axis.

Related literature

For related structures, see: Gowda, Foro et al. (2010[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o187.]); Gowda, Tokarčík et al. (2010[Gowda, B. T., Tokarčík, M., Rodrigues, V. Z., Kožíšek, J. & Fuess, H. (2010). Acta Cryst. E66, o1363.]).

[Scheme 1]

Experimental

Crystal data

  • C16H14N2O2

  • Mr = 266.29

  • Orthorhombic, P 21 21 21

  • a = 6.604 (1) Å

  • b = 13.358 (2) Å

  • c = 15.474 (2) Å

  • V = 1365.1 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.70 mm−1

  • T = 299 K

  • 0.35 × 0.30 × 0.25 mm
Data collection

  • Enraf–Nonius CAD-4 diffractometer

  • 3656 measured reflections

  • 1422 independent reflections

  • 1339 reflections with I > 2σ(I)

  • Rint = 0.117

  • 3 standard reflections every 120 min intensity decay: 0.5%
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.100

  • S = 1.06

  • 1422 reflections

  • 188 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.11 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O2i 0.86 (2) 2.04 (2) 2.884 (3) 167 (2)
N2—H2N⋯O1 0.91 (2) 1.77 (2) 2.671 (3) 167 (3)
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CAD-4-PC (Enraf–Nonius, 1996[Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987[Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.]); 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810051330/ng5082sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051330/ng5082Isup2.hkl

checkCIF report


Comment top

The amide moiety is an important constituent of many biologically significant compounds. As a part of studying the effect of substitutions on the structures of this class of compounds (Gowda, Foro et al., 2010; Gowda, Tokarčík et al., 2010), the crystal structure of N,N-bis(phenyl)-maleamide has been determined (I) (Fig. 1).

In the structure, the conformations of N—H and C=O bonds in both the amide groups of the C—NH—CO—CH ═CH—CO—NH—C segment are anti to each other. The two C=O bonds are also anti to each other, while one of them is syn to the adjacent C—H bond and the other is anti to its adjacent C—H bond. Further, C1—N1—C7—C8 and C11—N2—C10—C9 segments are nearly linear and so also the C1—N1—C7—O1 and C11—N2—C10—O2 segments. The torsion angles of C2—C1—N1—C7 and C6—C1—N1—C7 are 174.4 (3)° and -4.9 (4)°, respectively, while those of C12—C11—N2—C10 and C16—C11—N2—C10 are 40.4 (4)° and -143.9 (3)°.

The two phenyl rings in (I) make an interplanar angle of 41.2 (1)°. while the two benzene rings (C1 to C6 and C11 to C16) make the dihedral angles of 8.0 (1)° and 38.3 (1)°, respectively, with the central amide group (N1—C7—C8—C9—C10—N2).

The crystal structure (Fig. 2) exhibits both the intramolecular and intermolecular N–H···O hydrogen bonds (Table 1). The latter link the molecules into chains.

Related literature top

For related structures, see: Gowda, Foro et al. (2010); Gowda, Tokarčík et al. (2010).

Experimental top

A mixture of maleic acid (0.2 mol) and phosphorous oxy chloride (0.3 mol) were refluxed for 3 hrs on a water bath at 95° C. The aniline was added dropwise with stirring and continuing heating for about 30 min. It was later kept aside for 12 hrs for completion of the reaction. The reaction mixture was then added to ice. The precipitated product was washed with water, dilute HCl, dilute NaOH and again with water. The product was filtered, dried and recrystallized from DMF.

Prism like orange single crystals of the title compound used in X-ray diffraction studies were obtained by a slow evaporation of its DMF solution at room temperature.

Refinement top

The H atoms of the NH groups were located in a difference map and later restrained to the distance N—H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93 Å A l l H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

In the absence of significant anomalous dispersion effects, Friedel pairs were merged and the Δf"term set to zero.

Structure description top

The amide moiety is an important constituent of many biologically significant compounds. As a part of studying the effect of substitutions on the structures of this class of compounds (Gowda, Foro et al., 2010; Gowda, Tokarčík et al., 2010), the crystal structure of N,N-bis(phenyl)-maleamide has been determined (I) (Fig. 1).

In the structure, the conformations of N—H and C=O bonds in both the amide groups of the C—NH—CO—CH ═CH—CO—NH—C segment are anti to each other. The two C=O bonds are also anti to each other, while one of them is syn to the adjacent C—H bond and the other is anti to its adjacent C—H bond. Further, C1—N1—C7—C8 and C11—N2—C10—C9 segments are nearly linear and so also the C1—N1—C7—O1 and C11—N2—C10—O2 segments. The torsion angles of C2—C1—N1—C7 and C6—C1—N1—C7 are 174.4 (3)° and -4.9 (4)°, respectively, while those of C12—C11—N2—C10 and C16—C11—N2—C10 are 40.4 (4)° and -143.9 (3)°.

The two phenyl rings in (I) make an interplanar angle of 41.2 (1)°. while the two benzene rings (C1 to C6 and C11 to C16) make the dihedral angles of 8.0 (1)° and 38.3 (1)°, respectively, with the central amide group (N1—C7—C8—C9—C10—N2).

The crystal structure (Fig. 2) exhibits both the intramolecular and intermolecular N–H···O hydrogen bonds (Table 1). The latter link the molecules into chains.

For related structures, see: Gowda, Foro et al. (2010); Gowda, Tokarčík et al. (2010).

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
N,N'-Diphenylbut-2-enediamide top
Crystal data top
C16H14N2O2F(000) = 560
Mr = 266.29Dx = 1.296 Mg m−3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 6.604 (1) Åθ = 8.0–20.1°
b = 13.358 (2) ŵ = 0.70 mm−1
c = 15.474 (2) ÅT = 299 K
V = 1365.1 (3) Å3Prism, orange
Z = 40.35 × 0.30 × 0.25 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.117
Radiation source: fine-focus sealed tubeθmax = 66.9°, θmin = 4.4°
Graphite monochromatorh = 0→7
ω scansk = −15→15
3656 measured reflectionsl = −18→5
1422 independent reflections3 standard reflections every 120 min
1339 reflections with I > 2σ(I) intensity decay: 0.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0279P)2 + 0.0657P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.025
1422 reflectionsΔρmax = 0.11 e Å−3
188 parametersΔρmin = −0.13 e Å−3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0140 (9)
Crystal data top
C16H14N2O2V = 1365.1 (3) Å3
Mr = 266.29Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 6.604 (1) ŵ = 0.70 mm−1
b = 13.358 (2) ÅT = 299 K
c = 15.474 (2) Å0.35 × 0.30 × 0.25 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.117
3656 measured reflections3 standard reflections every 120 min
1422 independent reflections intensity decay: 0.5%
1339 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0432 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.11 e Å−3
1422 reflectionsΔρmin = −0.13 e Å−3
188 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
C1−0.0250 (3)0.71987 (19)0.85351 (17)0.0547 (6)
C2−0.0384 (3)0.8224 (2)0.8469 (2)0.0678 (7)
H20.06530.85790.82020.081*
C3−0.2036 (4)0.8730 (2)0.8794 (2)0.0761 (8)
H3−0.21050.94240.87470.091*
C4−0.3580 (4)0.8212 (3)0.9186 (2)0.0760 (8)
H4−0.47020.85500.94020.091*
C5−0.3449 (3)0.7192 (3)0.9256 (2)0.0750 (9)
H5−0.44900.68410.95250.090*
C6−0.1793 (3)0.6671 (2)0.89343 (17)0.0630 (7)
H6−0.17220.59780.89860.076*
C70.2087 (3)0.57754 (19)0.82283 (19)0.0610 (7)
C80.4088 (3)0.5604 (2)0.78135 (18)0.0653 (7)
H80.46460.61630.75450.078*
C90.5210 (3)0.4774 (2)0.7765 (2)0.0683 (8)
H90.64170.48790.74690.082*
C100.4997 (3)0.3727 (2)0.80698 (18)0.0597 (6)
C110.2874 (3)0.2512 (2)0.88312 (16)0.0581 (6)
C120.4328 (4)0.1895 (2)0.92070 (19)0.0731 (8)
H120.56750.20980.92280.088*
C130.3764 (4)0.0982 (3)0.9549 (2)0.0839 (9)
H130.47400.05700.97960.101*
C140.1789 (4)0.0676 (3)0.9529 (2)0.0882 (9)
H140.14230.00590.97580.106*
C150.0352 (4)0.1288 (2)0.9168 (2)0.0856 (9)
H15−0.09940.10830.91580.103*
C160.0868 (3)0.2196 (2)0.8821 (2)0.0687 (7)
H16−0.01240.26030.85780.082*
N10.1514 (2)0.67393 (16)0.81901 (16)0.0596 (6)
H1N0.227 (3)0.7171 (19)0.7929 (15)0.071*
N20.3325 (2)0.34685 (16)0.85126 (16)0.0617 (6)
H2N0.241 (3)0.3975 (19)0.8579 (19)0.074*
O10.1061 (2)0.51235 (14)0.85749 (17)0.0956 (8)
O20.6377 (2)0.31390 (16)0.79069 (14)0.0769 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0536 (9)0.0455 (12)0.0648 (13)0.0038 (9)0.0018 (10)0.0006 (15)
C20.0679 (10)0.0500 (13)0.0856 (18)0.0021 (11)0.0090 (13)0.0060 (19)
C30.0837 (14)0.0501 (14)0.0944 (18)0.0131 (12)−0.0005 (16)0.003 (2)
C40.0719 (12)0.0706 (18)0.0856 (19)0.0169 (14)0.0090 (14)0.003 (2)
C50.0609 (11)0.0733 (19)0.091 (2)0.0053 (11)0.0134 (13)0.009 (2)
C60.0547 (9)0.0530 (14)0.0812 (16)0.0001 (10)0.0045 (11)0.0110 (18)
C70.0570 (9)0.0424 (12)0.0836 (17)0.0014 (9)0.0108 (12)0.0025 (17)
C80.0576 (10)0.0479 (12)0.0903 (17)−0.0045 (10)0.0169 (12)0.0066 (18)
C90.0561 (9)0.0573 (15)0.091 (2)0.0007 (10)0.0161 (13)0.0009 (19)
C100.0553 (10)0.0499 (13)0.0740 (15)0.0027 (9)0.0055 (11)−0.0068 (17)
C110.0680 (10)0.0448 (12)0.0616 (13)0.0093 (10)0.0031 (11)−0.0048 (16)
C120.0715 (12)0.0619 (15)0.0860 (18)0.0168 (13)−0.0039 (13)0.004 (2)
C130.0977 (17)0.0612 (17)0.093 (2)0.0209 (16)−0.0119 (17)0.009 (2)
C140.1098 (18)0.0530 (15)0.102 (2)−0.0005 (16)0.0011 (18)0.017 (2)
C150.0820 (14)0.0579 (16)0.117 (3)−0.0023 (13)−0.0005 (16)0.003 (2)
C160.0657 (12)0.0547 (14)0.0856 (18)0.0070 (11)−0.0023 (13)0.0048 (19)
N10.0511 (8)0.0435 (10)0.0841 (14)−0.0005 (8)0.0082 (9)0.0044 (14)
N20.0568 (8)0.0468 (11)0.0816 (14)0.0093 (8)0.0079 (10)0.0028 (14)
O10.0772 (9)0.0461 (9)0.164 (2)0.0100 (8)0.0493 (12)0.0271 (16)
O20.0675 (8)0.0636 (12)0.0995 (13)0.0182 (9)0.0157 (9)−0.0071 (14)
Geometric parameters (Å, º) top
C1—C21.376 (4)C9—H90.9300
C1—C61.385 (3)C10—O21.230 (3)
C1—N11.421 (3)C10—N21.345 (3)
C2—C31.379 (4)C11—C161.390 (3)
C2—H20.9300C11—C121.392 (3)
C3—C41.374 (4)C11—N21.402 (3)
C3—H30.9300C12—C131.381 (5)
C4—C51.370 (5)C12—H120.9300
C4—H40.9300C13—C141.367 (4)
C5—C61.388 (3)C13—H130.9300
C5—H50.9300C14—C151.372 (4)
C6—H60.9300C14—H140.9300
C7—O11.227 (3)C15—C161.370 (4)
C7—N11.344 (3)C15—H150.9300
C7—C81.487 (3)C16—H160.9300
C8—C91.335 (4)N1—H1N0.862 (18)
C8—H80.9300N2—H2N0.912 (18)
C9—C101.482 (4)
C2—C1—C6119.5 (2)O2—C10—N2123.3 (3)
C2—C1—N1117.0 (2)O2—C10—C9117.9 (2)
C6—C1—N1123.4 (2)N2—C10—C9118.8 (2)
C1—C2—C3120.8 (3)C16—C11—C12118.9 (3)
C1—C2—H2119.6C16—C11—N2118.3 (2)
C3—C2—H2119.6C12—C11—N2122.7 (2)
C4—C3—C2120.1 (3)C13—C12—C11119.8 (2)
C4—C3—H3120.0C13—C12—H12120.1
C2—C3—H3120.0C11—C12—H12120.1
C5—C4—C3119.3 (3)C14—C13—C12120.8 (3)
C5—C4—H4120.3C14—C13—H13119.6
C3—C4—H4120.3C12—C13—H13119.6
C4—C5—C6121.3 (3)C13—C14—C15119.4 (3)
C4—C5—H5119.3C13—C14—H14120.3
C6—C5—H5119.3C15—C14—H14120.3
C1—C6—C5119.0 (3)C16—C15—C14121.0 (3)
C1—C6—H6120.5C16—C15—H15119.5
C5—C6—H6120.5C14—C15—H15119.5
O1—C7—N1122.9 (2)C15—C16—C11120.1 (3)
O1—C7—C8124.8 (2)C15—C16—H16120.0
N1—C7—C8112.3 (2)C11—C16—H16120.0
C9—C8—C7130.1 (3)C7—N1—C1129.0 (2)
C9—C8—H8114.9C7—N1—H1N119.9 (18)
C7—C8—H8114.9C1—N1—H1N111.1 (18)
C8—C9—C10135.5 (2)C10—N2—C11126.0 (2)
C8—C9—H9112.3C10—N2—H2N114.2 (19)
C10—C9—H9112.3C11—N2—H2N119.8 (18)
C6—C1—C2—C3−0.1 (5)C11—C12—C13—C14−0.5 (5)
N1—C1—C2—C3−179.4 (2)C12—C13—C14—C15−0.3 (5)
C1—C2—C3—C4−0.3 (5)C13—C14—C15—C160.5 (5)
C2—C3—C4—C50.5 (5)C14—C15—C16—C110.0 (5)
C3—C4—C5—C6−0.4 (6)C12—C11—C16—C15−0.7 (4)
C2—C1—C6—C50.2 (4)N2—C11—C16—C15−176.6 (3)
N1—C1—C6—C5179.5 (2)O1—C7—N1—C11.8 (5)
C4—C5—C6—C10.0 (5)C8—C7—N1—C1−177.7 (2)
O1—C7—C8—C9−3.9 (5)C2—C1—N1—C7174.4 (3)
N1—C7—C8—C9175.6 (3)C6—C1—N1—C7−4.9 (4)
C7—C8—C9—C100.5 (6)O2—C10—N2—C11−1.7 (4)
C8—C9—C10—O2−179.8 (3)C9—C10—N2—C11178.8 (3)
C8—C9—C10—N2−0.3 (6)C16—C11—N2—C10−143.9 (3)
C16—C11—C12—C131.0 (4)C12—C11—N2—C1040.4 (4)
N2—C11—C12—C13176.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.86 (2)2.04 (2)2.884 (3)167 (2)
N2—H2N···O10.91 (2)1.77 (2)2.671 (3)167 (3)
Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC16H14N2O2
Mr266.29
Crystal system, space groupOrthorhombic, P212121
Temperature (K)299
a, b, c (Å)6.604 (1), 13.358 (2), 15.474 (2)
V (Å3)1365.1 (3)
Z4
Radiation typeCu Kα
µ (mm−1)0.70
Crystal size (mm)0.35 × 0.30 × 0.25
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		3656, 1422, 1339
Rint0.117
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.100, 1.06
No. of reflections1422
No. of parameters188
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.11, −0.13

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.862 (18)2.036 (18)2.884 (3)167 (2)
N2—H2N···O10.912 (18)1.77 (2)2.671 (3)167 (3)
Symmetry code: (i) −x+1, y+1/2, −z+3/2.
 

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

First citationEnraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o117
https://doi.org/10.1107/S1600536810051330
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