4-Methyl-5-(4-nitro­benzyl­idene)-2-oxo-2,5-di­hydro-1H-pyrrole-3-carbo­nitrile

Gainsford, G.J.; Bhuiyan, M.D.H.; Kay, A.J.

doi:10.1107/S1600536813017066

organic compounds

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Volume 69| Part 7| July 2013| Page o1158

https://doi.org/10.1107/S1600536813017066

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4-Methyl-5-(4-nitrobenzylidene)-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

Graeme J. Gainsford,^a ^* M. Delower. H. Bhuiyan ^a and Andrew J. Kay ^a

^aCallaghan Innovation Research Limited, PO Box 31-310, Lower Hutt, New Zealand
^*Correspondence e-mail: g.gainsford@irl.cri.nz

(Received 7 June 2013; accepted 19 June 2013; online 26 June 2013)

Molecules of the potential non-linear optical title compound, C₁₃H₉N₃O₃, form dimeric stacks of molecules along the a axis cross-linked around inversion centers by N—H⋯O hydrogen bonds and weak (phenyl)C—H⋯O intermolecular interactions, forming a `collaboration' of R₂²(8) and R₂²(16) ring motifs. The molecules are then further linked by weak C—H⋯O and C—H⋯N interactions into sheets parallel to (121).

Related literature

For hydrogen-bonding motifs, see: Bernstein et al. (1995 ). For chemical synthesis literature, see: Shrestha-Dawadi & Lugtenburg (2007 ). For background literature, see: Bert et al. (2006 ); Colin et al. (2002 ); Hasan et al. (2012 ); Stephen et al. (2011 ); Tarek et al. (2013 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₃H₉N₃O₃
M_r = 255.23
Monoclinic, P 2₁ /c
a = 3.7456 (2) Å
b = 14.9193 (9) Å
c = 21.6077 (17) Å
β = 92.273 (7)°
V = 1206.52 (14) Å³
Z = 4
Cu Kα radiation
μ = 0.86 mm⁻¹
T = 120 K
0.44 × 0.05 × 0.03 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.633, T_max = 1.000
7096 measured reflections
2283 independent reflections
1941 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.139
S = 1.05
2283 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	1.98	2.8256 (18)	159
C9—H9⋯O1ⁱⁱ	0.95	2.43	3.336 (2)	159
C12—H12⋯N2ⁱⁱⁱ	0.95	2.59	3.374 (3)	141
C13—H13⋯O2^iv	0.95	2.58	3.372 (2)	141
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813017066/jj2169sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813017066/jj2169Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813017066/jj2169Isup3.cml

checkCIF report

Comment top

Oxopyrroles and their analogues are the key intermediate for many biologically active compounds (Shrestha-Dawadi & Lugtenburg, 2007) and pigments (Colin et al., 2002). Many studies have been dedicated to the synthesis and spectroscopic characterization of oxopyrroles (Tarek et al., 2013; Hasan et al. 2012; Bert et al., 2006) to improve their features. Structural modification has been carried out on the oxypyrrole ring through the introduction of a thiophene ring (Stephen et al., 2011) as an efficient donor and as a precursor for use in organic solar cells. Structural modification via the incorporation of an electron-withdrawing group has not been reported.

As a part of our efforts to develop donor-π-acceptor molecules for non-linear optical devices, we have synthesized the title compound in which the oxopyrrole nitrile analogue acts as donor and the nitro group is the acceptor linked by a phenyl-methylene bridge. The molecule crystallizes with one independent molecule in the asymmetric unit (Fig. 1). The 1H-pyrole ring is planar with maximum deviation out of plane of 0.018 (2) Å for C2; it makes an angle of 33.99 (9)° with the planar phenyl ring (C8–C13). The nitro group is further twisted by 5.24 (10)° from the latter ring in response to a hydrogen bond interaction with O2. There are few related structures reported and none with linking 5- and 6-membered rings (Allen, 2002; CSD Version 5.34, with Nov 2012 updates).

The molecules form dimers utilizing N—H···O hydrogen bonds about inversion centers of symmetry, packing into approximate planes parallel to the (1,-2,0) plane (Fig. 2). This interaction is further stabilized by weak phenyl(C9)–H ···O1 intermolecular interactions between the adjacent dimers, producing an overall packing "collaboration" of R₂²(8) and R₂²(16) ring motifs (Bernstein et al., 1995). Other three-dimensional cross-links are provided by chain interactions (not shown in Fig. 2) with weak phenylC–H···O and phenylC–H···N intermolecular contacts (Table 1), linling the molecules into sheets parallel to the (121) plane. .

Related literature top

For hydrogen-bonding motifs, see: Bernstein et al. (1995). For chemical synthesis literature, see: Shrestha-Dawadi & Lugtenburg (2007). For background literature, see: Bert et al. (2006); Colin et al. (2002); Hasan et al. (2012); Stephen et al. (2011); Tarek et al. (2013). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

A mixture of 3-cyano-4-methyl-3-pyrrolin-2-one (Shrestha-Dawadi & Lugtenburg, 2007) (1.0 g), 4-nitro benzaldehyde (1.6 g), sodium acetate (1.8 g) and acetic acid (50 ml) was refluxed for 3 h. under an inert atmosphere. The mixture was stirred overnight, and cooled to 0° C. The resultant precipitate was collected by filtration and washed with cold hexanes to yield the pure chromophore 4-methyl-5-(4-nitro-benzylidene)-2-oxo-2,5-dihydro-1H-pyrrole- 3-carbonitrile (1.2 g, 57%) as a yellow solid. Crystals were grown by slow evaporation of an acetone solution. m.p. 277–80° C.

Structure description top

For hydrogen-bonding motifs, see: Bernstein et al. (1995). For chemical synthesis literature, see: Shrestha-Dawadi & Lugtenburg (2007). For background literature, see: Bert et al. (2006); Colin et al. (2002); Hasan et al. (2012); Stephen et al. (2011); Tarek et al. (2013). For a description of the Cambridge Structural Database, see: Allen (2002).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: ORTEP-3 in WinGX (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Asymmetric unit atoms for (I) with ellipsoid probability of 50% for non-hydrogen atoms.
	Fig. 2. Packing diagram of (I) viewed along the a axis. Intermolecular contacts are shown as blue dotted lines. Symmetry: (i) -1 + x, y, z (ii) 1 - x, 1 - y, 1 - z (iii) 1 - x, -1/2 + y, 1/2 - z.

4-Methyl-5-(4-nitrobenzylidene)-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile top

Crystal data top

C₁₃H₉N₃O₃	Z = 4
M_r = 255.23	F(000) = 528
Monoclinic, P2₁/c	D_x = 1.405 Mg m⁻³
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 3.7456 (2) Å	µ = 0.86 mm⁻¹
b = 14.9193 (9) Å	T = 120 K
c = 21.6077 (17) Å	Needle, yellow
β = 92.273 (7)°	0.44 × 0.05 × 0.03 mm
V = 1206.52 (14) Å³

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2283 independent reflections
Radiation source: fine-focus sealed tube	1941 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 10.6501 pixels mm^-1	θ_max = 70.0°, θ_min = 3.6°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −17→18
T_min = 0.633, T_max = 1.000	l = −26→18
7096 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0824P)² + 0.3085P] where P = (F_o² + 2F_c²)/3
2283 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₃H₉N₃O₃	V = 1206.52 (14) Å³
M_r = 255.23	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 3.7456 (2) Å	µ = 0.86 mm⁻¹
b = 14.9193 (9) Å	T = 120 K
c = 21.6077 (17) Å	0.44 × 0.05 × 0.03 mm
β = 92.273 (7)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2283 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	1941 reflections with I > 2σ(I)
T_min = 0.633, T_max = 1.000	R_int = 0.042
7096 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.05	Δρ_max = 0.25 e Å⁻³
2283 reflections	Δρ_min = −0.25 e Å⁻³
173 parameters

Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

(MNa)⁺ m/z 278.0540; C₁₃H₉N₃O₃ requires (MNa)⁺ m/z 278.0542). ¹H NMR (500 MHz, d₆-DMSO) 2.46 (s, 3H, CH₃), 6.84 (s, 1H, CH), 7.88 (d, 2H, J = 4.9 Hz, ArH), 8.25 (d, 2H, J = 4.9 Hz, ArH), 10.91 (s, 1H, NH). ¹³C NMR (75 MHz, d₆ –DMSO) 12.3, 105.9, 112.7, 113.4, 123.9, 130.9, 138.2, 139.9, 146.7, 161.7, 166.9.

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

	x	y	z	U_iso*/U_eq
O1	0.8538 (3)	0.44087 (8)	0.56486 (6)	0.0277 (3)
O2	0.9729 (4)	0.64031 (9)	0.18759 (7)	0.0452 (4)
O3	1.1572 (4)	0.52825 (10)	0.13455 (7)	0.0453 (4)
N1	0.7576 (4)	0.40243 (9)	0.46186 (7)	0.0243 (3)
H1	0.8491	0.4502	0.4446	0.029*
N2	0.3889 (4)	0.24706 (12)	0.63898 (9)	0.0403 (4)
N3	1.0168 (4)	0.55927 (10)	0.17993 (8)	0.0323 (4)
C1	0.7387 (4)	0.39026 (11)	0.52376 (8)	0.0236 (4)
C2	0.5581 (4)	0.30283 (11)	0.53143 (9)	0.0253 (4)
C3	0.4940 (4)	0.26523 (11)	0.47533 (8)	0.0252 (4)
C4	0.6126 (4)	0.32905 (11)	0.42854 (8)	0.0246 (4)
C5	0.4693 (5)	0.27012 (11)	0.59072 (9)	0.0283 (4)
C6	0.3332 (5)	0.17567 (11)	0.46080 (9)	0.0296 (4)
H6A	0.1407	0.1825	0.4291	0.044*
H6B	0.2362	0.1501	0.4984	0.044*
H6C	0.5171	0.1356	0.4454	0.044*
C7	0.5892 (4)	0.31806 (11)	0.36711 (8)	0.0264 (4)
H7	0.4945	0.2624	0.3527	0.032*
C8	0.6925 (4)	0.38178 (11)	0.31925 (8)	0.0256 (4)
C9	0.6636 (4)	0.47494 (11)	0.32720 (9)	0.0268 (4)
H9	0.5724	0.4981	0.3644	0.032*
C10	0.7663 (5)	0.53323 (11)	0.28161 (9)	0.0283 (4)
H10	0.7463	0.5962	0.2869	0.034*
C11	0.8990 (4)	0.49794 (12)	0.22809 (8)	0.0276 (4)
C12	0.9235 (5)	0.40627 (12)	0.21750 (9)	0.0287 (4)
H12	1.0116	0.3838	0.1799	0.034*
C13	0.8157 (5)	0.34892 (12)	0.26339 (8)	0.0285 (4)
H13	0.8255	0.2860	0.2569	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0363 (6)	0.0202 (6)	0.0267 (7)	−0.0029 (5)	0.0031 (5)	−0.0007 (5)
O2	0.0724 (10)	0.0219 (7)	0.0415 (9)	−0.0063 (6)	0.0049 (7)	0.0049 (6)
O3	0.0579 (9)	0.0402 (8)	0.0392 (9)	0.0065 (7)	0.0202 (7)	0.0088 (7)
N1	0.0314 (7)	0.0158 (7)	0.0258 (8)	−0.0023 (5)	0.0032 (6)	0.0007 (6)
N2	0.0449 (9)	0.0378 (9)	0.0387 (11)	−0.0049 (7)	0.0067 (8)	0.0095 (8)
N3	0.0379 (8)	0.0273 (8)	0.0315 (9)	−0.0017 (6)	0.0015 (7)	0.0049 (7)
C1	0.0264 (7)	0.0178 (8)	0.0268 (9)	0.0020 (6)	0.0036 (6)	0.0007 (7)
C2	0.0278 (8)	0.0184 (8)	0.0300 (10)	0.0014 (6)	0.0054 (7)	0.0025 (7)
C3	0.0268 (8)	0.0179 (8)	0.0313 (10)	0.0005 (6)	0.0048 (7)	0.0010 (7)
C4	0.0283 (8)	0.0168 (8)	0.0289 (9)	0.0012 (6)	0.0045 (7)	0.0001 (7)
C5	0.0311 (8)	0.0196 (8)	0.0342 (11)	−0.0010 (6)	0.0023 (7)	0.0024 (7)
C6	0.0348 (8)	0.0188 (8)	0.0356 (10)	−0.0040 (7)	0.0060 (7)	−0.0009 (7)
C7	0.0296 (8)	0.0179 (8)	0.0320 (10)	−0.0005 (6)	0.0041 (7)	−0.0014 (7)
C8	0.0256 (7)	0.0230 (8)	0.0280 (10)	−0.0008 (6)	0.0003 (7)	−0.0004 (7)
C9	0.0285 (8)	0.0231 (9)	0.0290 (10)	0.0015 (6)	0.0038 (7)	−0.0033 (7)
C10	0.0332 (8)	0.0197 (8)	0.0318 (10)	0.0006 (7)	0.0000 (7)	−0.0001 (7)
C11	0.0289 (8)	0.0253 (9)	0.0285 (10)	−0.0012 (7)	0.0014 (7)	0.0035 (8)
C12	0.0336 (8)	0.0256 (9)	0.0272 (10)	0.0031 (7)	0.0043 (7)	−0.0007 (7)
C13	0.0365 (9)	0.0206 (8)	0.0287 (10)	0.0018 (7)	0.0027 (7)	−0.0019 (7)

Geometric parameters (Å, º) top

O1—C1	1.231 (2)	C6—H6B	0.9800
O2—N3	1.232 (2)	C6—H6C	0.9800
O3—N3	1.222 (2)	C7—C8	1.468 (2)
N1—C1	1.354 (2)	C7—H7	0.9500
N1—C4	1.407 (2)	C8—C13	1.398 (2)
N1—H1	0.8800	C8—C9	1.405 (2)
N2—C5	1.149 (3)	C9—C10	1.380 (2)
N3—C11	1.467 (2)	C9—H9	0.9500
C1—C2	1.482 (2)	C10—C11	1.381 (3)
C2—C3	1.349 (3)	C10—H10	0.9500
C2—C5	1.423 (3)	C11—C12	1.390 (2)
C3—C4	1.470 (2)	C12—C13	1.382 (3)
C3—C6	1.494 (2)	C12—H12	0.9500
C4—C7	1.337 (3)	C13—H13	0.9500
C6—H6A	0.9800

C1—N1—C4	111.50 (14)	H6A—C6—H6C	109.5
C1—N1—H1	124.3	H6B—C6—H6C	109.5
C4—N1—H1	124.3	C4—C7—C8	127.68 (16)
O3—N3—O2	122.93 (16)	C4—C7—H7	116.2
O3—N3—C11	118.96 (15)	C8—C7—H7	116.2
O2—N3—C11	118.11 (16)	C13—C8—C9	118.82 (16)
O1—C1—N1	126.85 (15)	C13—C8—C7	119.10 (15)
O1—C1—C2	127.44 (16)	C9—C8—C7	122.06 (16)
N1—C1—C2	105.70 (15)	C10—C9—C8	120.73 (16)
C3—C2—C5	128.83 (16)	C10—C9—H9	119.6
C3—C2—C1	109.36 (15)	C8—C9—H9	119.6
C5—C2—C1	121.80 (16)	C9—C10—C11	118.51 (16)
C2—C3—C4	107.50 (15)	C9—C10—H10	120.7
C2—C3—C6	128.09 (16)	C11—C10—H10	120.7
C4—C3—C6	124.41 (16)	C10—C11—C12	122.76 (16)
C7—C4—N1	127.73 (15)	C10—C11—N3	118.99 (16)
C7—C4—C3	126.41 (16)	C12—C11—N3	118.24 (16)
N1—C4—C3	105.85 (15)	C13—C12—C11	117.89 (16)
N2—C5—C2	176.98 (19)	C13—C12—H12	121.1
C3—C6—H6A	109.5	C11—C12—H12	121.1
C3—C6—H6B	109.5	C12—C13—C8	121.21 (16)
H6A—C6—H6B	109.5	C12—C13—H13	119.4
C3—C6—H6C	109.5	C8—C13—H13	119.4

C4—N1—C1—O1	177.31 (15)	C3—C4—C7—C8	177.49 (16)
C4—N1—C1—C2	−1.53 (17)	C4—C7—C8—C13	148.90 (18)
O1—C1—C2—C3	−175.91 (16)	C4—C7—C8—C9	−32.6 (3)
N1—C1—C2—C3	2.92 (18)	C13—C8—C9—C10	−2.2 (3)
O1—C1—C2—C5	5.4 (3)	C7—C8—C9—C10	179.34 (16)
N1—C1—C2—C5	−175.75 (15)	C8—C9—C10—C11	−0.2 (3)
C5—C2—C3—C4	175.48 (16)	C9—C10—C11—C12	1.9 (3)
C1—C2—C3—C4	−3.06 (18)	C9—C10—C11—N3	−178.58 (16)
C5—C2—C3—C6	−4.5 (3)	O3—N3—C11—C10	174.92 (17)
C1—C2—C3—C6	176.91 (15)	O2—N3—C11—C10	−4.3 (3)
C1—N1—C4—C7	−179.52 (16)	O3—N3—C11—C12	−5.6 (3)
C1—N1—C4—C3	−0.25 (18)	O2—N3—C11—C12	175.26 (17)
C2—C3—C4—C7	−178.61 (16)	C10—C11—C12—C13	−1.2 (3)
C6—C3—C4—C7	1.4 (3)	N3—C11—C12—C13	179.27 (16)
C2—C3—C4—N1	2.11 (18)	C11—C12—C13—C8	−1.3 (3)
C6—C3—C4—N1	−177.87 (15)	C9—C8—C13—C12	2.9 (3)
N1—C4—C7—C8	−3.4 (3)	C7—C8—C13—C12	−178.56 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	1.98	2.8256 (18)	159
C9—H9···O1ⁱⁱ	0.95	2.43	3.336 (2)	159
C12—H12···N2ⁱⁱⁱ	0.95	2.59	3.374 (3)	141
C13—H13···O2^iv	0.95	2.58	3.372 (2)	141

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x+1, −y+1/2, z−1/2; (iv) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉N₃O₃
M_r	255.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	3.7456 (2), 14.9193 (9), 21.6077 (17)
β (°)	92.273 (7)
V (Å³)	1206.52 (14)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.44 × 0.05 × 0.03

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Atlas)
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.633, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7096, 2283, 1941
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.139, 1.05
No. of reflections	2283
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.25

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL2012 (Sheldrick, 2008), ORTEP-3 in WinGX (Farrugia, 2012) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	1.98	2.8256 (18)	159
C9—H9···O1ⁱⁱ	0.95	2.43	3.336 (2)	159
C12—H12···N2ⁱⁱⁱ	0.95	2.59	3.374 (3)	141
C13—H13···O2^iv	0.95	2.58	3.372 (2)	141

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x+1, −y+1/2, z−1/2; (iv) −x+2, y−1/2, −z+1/2.

Acknowledgements

The authors thank Dr J. Wikaira of the University of Canterbury for the data collection.

References

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

4-Methyl-5-(4-nitro­benzyl­­idene)-2-oxo-2,5-di­hydro-1H-pyrrole-3-carbo­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

4-Methyl-5-(4-nitrobenzylidene)-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile