4-Dimethyl­amino-1-(4-meth­oxy­phen­yl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

Abdel-Wahab, B.F.; Mohamed, H.A.; Farahat, A.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813004893

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o437

doi:10.1107/S1600536813004893

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4-Dimethylamino-1-(4-methoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

Bakr F. Abdel-Wahab,^a ‡ Hanan A. Mohamed,^a Abdelbasset A. Farahat,^b Seik Weng Ng ^c,^d and Edward R. T. Tiekink ^c ^*

^aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt, ^bDepartment of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 14 February 2013; accepted 19 February 2013; online 23 February 2013)

In the title compound, C₁₄H₁₃N₃O₃, a twist occurs, as seen in the dihedral angle of 53.60 (12)° between the pyrrole and benzene rings. A three-dimensional architecture is formed in the crystal whereby layers of molecules in the ac plane are connected by C—H⋯O and C—H⋯π interactions.

Related literature

For background to the biological activity exhibited by pyrroles and pyranopyrroles, see: Amer et al. (2008 , 2009 ).

Experimental

Crystal data

C₁₄H₁₃N₃O₃
M_r = 271.27
Monoclinic, P 2₁ /c
a = 12.7408 (14) Å
b = 7.8520 (9) Å
c = 14.4194 (18) Å
β = 115.163 (14)°
V = 1305.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.40 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.869, T_max = 1.000
8113 measured reflections
3020 independent reflections
1772 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.153
S = 1.04
3020 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O2ⁱ	0.96	2.54	3.397 (3)	149
C12—H12⋯O1ⁱⁱ	0.93	2.54	3.384 (3)	151
C5—H5B⋯Cg1ⁱⁱⁱ	0.96	2.94	3.848 (3)	158
C6—H6B⋯Cg1^iv	0.96	3.00	3.781 (3)	140
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813004893/hb7042sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004893/hb7042Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004893/hb7042Isup3.cml

checkCIF report

Comment top

The title compound (I) was investigated owing to the biological activities exhibited pyrroles and pyranopyrrole analogues (Amer et al. 2009; Amer et al. 2008). Herein, its crystal structure determination is described.

Crystallography shows that fusion of 1-(4-methoxyphenyl)-4-oxopyrrolidine-3-carbonitrile with excess 1,1-dimethoxy-N,N-dimethylmethanamine afforded 4-(dimethylamino)-1-(4-methoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile (I) not the expected 2-((dimethylamino)methylene)-1-(4-methoxyphenyl)-4-oxopyrrolidine-3-carbonitrile (II).

In (I), Fig. 1, the dihedral angle of 53.60 (12)° between the pyrrole (r.m.s. deviation = 0.005 Å) and benzene rings indicates a significant twist in the molecule. The methoxy substituent is twisted out of the plane of the ring to which it is attached as seen in the value of the C14—O3—C11—C10 torsion angle of -13.9 (4)°. The dimethylamino group is also slightly twisted out of the plane through the pyrrole ring to which it is attached; the C5—N2—C2—C1 torsion angle is 8.7 (3)°.

The three-dimensional architecture of (I) is consolidated by C—H···O interactions, involving both carbonyl-O atoms, as well as C—H···π interactions whereby the benzene ring serves as a bridge between molecules, Fig. 2 and Table 1.

Related literature top

For background to the biological activity exhibited by pyrroles and pyranopyrroles, see: Amer et al. (2008, 2009).

Experimental top

A mixture of 1-(4-methoxyphenyl)-4-oxopyrrolidine-3-carbonitrile (0.22 g, 0.001 M) and excess 1,1-dimethoxy-N,N-dimethylmethanamine (0.2 ml) was heated under reflux for about 1.5 h on water bath. The resultant solid was filtered and dried. Re-crystallization was by slow evaporation of its DMF solution which yielded yellow prisms in 28% yield. M.pt. 482–483 K.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.
	Fig. 2. A view of the crystal packing in projection down the a axis. The C—H···O and C—H···π interactions are shown as orange and purple dashed lines, respectively.

4-Dimethylamino-1-(4-methoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile top

Crystal data top

C₁₄H₁₃N₃O₃	F(000) = 568
M_r = 271.27	D_x = 1.380 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1717 reflections
a = 12.7408 (14) Å	θ = 2.9–27.5°
b = 7.8520 (9) Å	µ = 0.10 mm⁻¹
c = 14.4194 (18) Å	T = 295 K
β = 115.163 (14)°	Prism, yellow
V = 1305.6 (3) Å³	0.40 × 0.20 × 0.10 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3020 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1772 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.040
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.9°
ω scan	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→10
T_min = 0.869, T_max = 1.000	l = −17→18
8113 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0573P)² + 0.268P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3020 reflections	Δρ_max = 0.20 e Å⁻³
184 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0065 (17)

Crystal data top

C₁₄H₁₃N₃O₃	V = 1305.6 (3) Å³
M_r = 271.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.7408 (14) Å	µ = 0.10 mm⁻¹
b = 7.8520 (9) Å	T = 295 K
c = 14.4194 (18) Å	0.40 × 0.20 × 0.10 mm
β = 115.163 (14)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3020 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	1772 reflections with I > 2σ(I)
T_min = 0.869, T_max = 1.000	R_int = 0.040
8113 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
3020 reflections	Δρ_min = −0.17 e Å⁻³
184 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

	x	y	z	U_iso*/U_eq
O1	0.87550 (12)	0.4211 (2)	0.83764 (12)	0.0638 (5)
O2	0.54480 (12)	0.7013 (2)	0.63309 (13)	0.0643 (5)
O3	0.86456 (14)	0.6113 (3)	0.40226 (13)	0.0700 (5)
N1	0.72098 (13)	0.5628 (2)	0.71557 (13)	0.0457 (5)
N2	0.74285 (15)	0.4605 (3)	0.96511 (14)	0.0517 (5)
N3	0.43202 (18)	0.7134 (3)	0.82506 (18)	0.0764 (7)
C1	0.78270 (17)	0.4912 (3)	0.81026 (17)	0.0461 (5)
C2	0.71002 (16)	0.5147 (3)	0.87029 (16)	0.0448 (5)
C3	0.60974 (16)	0.5976 (3)	0.80526 (16)	0.0463 (6)
C4	0.61362 (16)	0.6288 (3)	0.70794 (17)	0.0471 (6)
C5	0.85888 (19)	0.3921 (4)	1.03016 (18)	0.0665 (8)
H5A	0.9024	0.3797	0.9901	0.100*
H5B	0.8511	0.2831	1.0567	0.100*
H5C	0.8987	0.4689	1.0859	0.100*
C6	0.6647 (2)	0.4773 (4)	1.01516 (18)	0.0644 (7)
H6A	0.5885	0.4397	0.9693	0.097*
H6B	0.6615	0.5944	1.0329	0.097*
H6C	0.6929	0.4089	1.0761	0.097*
C7	0.51255 (19)	0.6588 (3)	0.81992 (18)	0.0551 (6)
C8	0.75727 (16)	0.5680 (3)	0.63493 (16)	0.0445 (5)
C9	0.68625 (17)	0.5068 (3)	0.53895 (17)	0.0501 (6)
H9	0.6157	0.4570	0.5278	0.060*
C10	0.71847 (18)	0.5185 (3)	0.45933 (18)	0.0528 (6)
H10	0.6694	0.4782	0.3947	0.063*
C11	0.82415 (18)	0.5903 (3)	0.47577 (18)	0.0522 (6)
C12	0.89700 (18)	0.6489 (3)	0.57264 (18)	0.0558 (6)
H12	0.9687	0.6952	0.5843	0.067*
C13	0.86383 (17)	0.6389 (3)	0.65152 (17)	0.0518 (6)
H13	0.9127	0.6796	0.7161	0.062*
C14	0.8062 (2)	0.5219 (4)	0.3082 (2)	0.0729 (8)
H14A	0.8420	0.5479	0.2632	0.109*
H14B	0.7263	0.5559	0.2766	0.109*
H14C	0.8111	0.4016	0.3213	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0468 (9)	0.0708 (13)	0.0703 (11)	0.0171 (8)	0.0215 (8)	0.0120 (9)
O2	0.0497 (9)	0.0694 (13)	0.0663 (10)	0.0130 (8)	0.0174 (8)	0.0112 (10)
O3	0.0740 (11)	0.0761 (14)	0.0704 (11)	−0.0066 (9)	0.0409 (9)	0.0007 (10)
N1	0.0349 (9)	0.0490 (12)	0.0492 (10)	0.0021 (8)	0.0143 (8)	0.0038 (9)
N2	0.0497 (10)	0.0507 (13)	0.0499 (11)	−0.0038 (9)	0.0165 (8)	−0.0009 (9)
N3	0.0643 (13)	0.0814 (19)	0.0946 (17)	0.0171 (12)	0.0445 (12)	0.0116 (14)
C1	0.0391 (11)	0.0387 (13)	0.0550 (13)	−0.0014 (9)	0.0146 (9)	−0.0004 (11)
C2	0.0408 (11)	0.0387 (13)	0.0486 (12)	−0.0057 (9)	0.0131 (9)	−0.0051 (10)
C3	0.0373 (11)	0.0429 (14)	0.0555 (13)	−0.0018 (9)	0.0167 (9)	−0.0026 (11)
C4	0.0358 (11)	0.0446 (14)	0.0558 (13)	0.0010 (9)	0.0145 (9)	0.0002 (11)
C5	0.0574 (14)	0.070 (2)	0.0572 (14)	0.0056 (12)	0.0102 (11)	0.0095 (13)
C6	0.0663 (15)	0.071 (2)	0.0569 (15)	−0.0048 (13)	0.0276 (12)	−0.0023 (13)
C7	0.0495 (13)	0.0514 (16)	0.0641 (15)	0.0005 (11)	0.0240 (11)	0.0017 (12)
C8	0.0389 (11)	0.0400 (13)	0.0520 (13)	0.0016 (9)	0.0168 (9)	0.0016 (10)
C9	0.0388 (11)	0.0452 (14)	0.0610 (14)	−0.0034 (9)	0.0162 (10)	0.0007 (12)
C10	0.0474 (12)	0.0538 (16)	0.0530 (13)	−0.0010 (10)	0.0174 (10)	−0.0009 (12)
C11	0.0524 (13)	0.0473 (15)	0.0604 (14)	0.0034 (10)	0.0273 (11)	0.0045 (12)
C12	0.0428 (12)	0.0532 (16)	0.0731 (16)	−0.0064 (10)	0.0262 (11)	−0.0014 (13)
C13	0.0385 (11)	0.0518 (15)	0.0586 (14)	−0.0045 (10)	0.0144 (10)	−0.0051 (12)
C14	0.0936 (19)	0.065 (2)	0.0674 (17)	0.0095 (15)	0.0411 (15)	0.0042 (15)

Geometric parameters (Å, º) top

O1—C1	1.208 (2)	C5—H5C	0.9600
O2—C4	1.206 (3)	C6—H6A	0.9600
O3—C11	1.371 (3)	C6—H6B	0.9600
O3—C14	1.424 (3)	C6—H6C	0.9600
N1—C1	1.373 (3)	C8—C9	1.378 (3)
N1—C8	1.423 (3)	C8—C13	1.391 (3)
N1—C4	1.422 (3)	C9—C10	1.377 (3)
N2—C2	1.319 (3)	C9—H9	0.9300
N2—C6	1.463 (3)	C10—C11	1.384 (3)
N2—C5	1.475 (3)	C10—H10	0.9300
N3—C7	1.143 (3)	C11—C12	1.386 (3)
C1—C2	1.524 (3)	C12—C13	1.374 (3)
C2—C3	1.384 (3)	C12—H12	0.9300
C3—C7	1.425 (3)	C13—H13	0.9300
C3—C4	1.446 (3)	C14—H14A	0.9600
C5—H5A	0.9600	C14—H14B	0.9600
C5—H5B	0.9600	C14—H14C	0.9600

C11—O3—C14	117.5 (2)	N2—C6—H6C	109.5
C1—N1—C8	125.20 (17)	H6A—C6—H6C	109.5
C1—N1—C4	110.58 (18)	H6B—C6—H6C	109.5
C8—N1—C4	124.21 (17)	N3—C7—C3	175.1 (3)
C2—N2—C6	119.99 (19)	C9—C8—C13	119.2 (2)
C2—N2—C5	124.6 (2)	C9—C8—N1	120.52 (18)
C6—N2—C5	115.32 (19)	C13—C8—N1	120.23 (19)
O1—C1—N1	125.4 (2)	C10—C9—C8	120.9 (2)
O1—C1—C2	128.0 (2)	C10—C9—H9	119.6
N1—C1—C2	106.60 (17)	C8—C9—H9	119.6
N2—C2—C3	130.4 (2)	C9—C10—C11	119.8 (2)
N2—C2—C1	123.25 (19)	C9—C10—H10	120.1
C3—C2—C1	106.32 (19)	C11—C10—H10	120.1
C2—C3—C7	131.9 (2)	O3—C11—C12	115.4 (2)
C2—C3—C4	109.54 (18)	O3—C11—C10	125.0 (2)
C7—C3—C4	118.50 (18)	C12—C11—C10	119.6 (2)
O2—C4—N1	123.4 (2)	C13—C12—C11	120.4 (2)
O2—C4—C3	129.56 (19)	C13—C12—H12	119.8
N1—C4—C3	106.97 (17)	C11—C12—H12	119.8
N2—C5—H5A	109.5	C12—C13—C8	120.1 (2)
N2—C5—H5B	109.5	C12—C13—H13	119.9
H5A—C5—H5B	109.5	C8—C13—H13	119.9
N2—C5—H5C	109.5	O3—C14—H14A	109.5
H5A—C5—H5C	109.5	O3—C14—H14B	109.5
H5B—C5—H5C	109.5	H14A—C14—H14B	109.5
N2—C6—H6A	109.5	O3—C14—H14C	109.5
N2—C6—H6B	109.5	H14A—C14—H14C	109.5
H6A—C6—H6B	109.5	H14B—C14—H14C	109.5

C8—N1—C1—O1	−0.9 (4)	C2—C3—C4—O2	−177.8 (2)
C4—N1—C1—O1	177.9 (2)	C7—C3—C4—O2	−0.2 (4)
C8—N1—C1—C2	−179.66 (19)	C2—C3—C4—N1	−0.4 (3)
C4—N1—C1—C2	−0.9 (2)	C7—C3—C4—N1	177.2 (2)
C6—N2—C2—C3	3.3 (4)	C1—N1—C8—C9	126.3 (2)
C5—N2—C2—C3	−172.2 (2)	C4—N1—C8—C9	−52.3 (3)
C6—N2—C2—C1	−175.7 (2)	C1—N1—C8—C13	−55.3 (3)
C5—N2—C2—C1	8.7 (3)	C4—N1—C8—C13	126.1 (2)
O1—C1—C2—N2	1.2 (4)	C13—C8—C9—C10	−1.4 (4)
N1—C1—C2—N2	179.9 (2)	N1—C8—C9—C10	177.0 (2)
O1—C1—C2—C3	−178.1 (2)	C8—C9—C10—C11	0.9 (4)
N1—C1—C2—C3	0.6 (2)	C14—O3—C11—C12	166.8 (2)
N2—C2—C3—C7	3.6 (4)	C14—O3—C11—C10	−13.9 (4)
C1—C2—C3—C7	−177.2 (2)	C9—C10—C11—O3	−178.9 (2)
N2—C2—C3—C4	−179.3 (2)	C9—C10—C11—C12	0.4 (4)
C1—C2—C3—C4	−0.1 (2)	O3—C11—C12—C13	178.1 (2)
C1—N1—C4—O2	178.4 (2)	C10—C11—C12—C13	−1.3 (4)
C8—N1—C4—O2	−2.8 (4)	C11—C12—C13—C8	0.8 (4)
C1—N1—C4—C3	0.8 (2)	C9—C8—C13—C12	0.6 (4)
C8—N1—C4—C3	179.62 (19)	N1—C8—C13—C12	−177.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2ⁱ	0.96	2.54	3.397 (3)	149
C12—H12···O1ⁱⁱ	0.93	2.54	3.384 (3)	151
C5—H5B···Cg1ⁱⁱⁱ	0.96	2.94	3.848 (3)	158
C6—H6B···Cg1^iv	0.96	3.00	3.781 (3)	140

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2; (iii) x, −y−1/2, z−1/2; (iv) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₃O₃
M_r	271.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.7408 (14), 7.8520 (9), 14.4194 (18)
β (°)	115.163 (14)
V (Å³)	1305.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.869, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8113, 3020, 1772
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.153, 1.04
No. of reflections	3020
No. of parameters	184
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.17

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2ⁱ	0.96	2.54	3.397 (3)	149
C12—H12···O1ⁱⁱ	0.93	2.54	3.384 (3)	151
C5—H5B···Cg1ⁱⁱⁱ	0.96	2.94	3.848 (3)	158
C6—H6B···Cg1^iv	0.96	3.00	3.781 (3)	140

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+3/2; (iii) x, −y−1/2, z−1/2; (iv) x, −y+1/2, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: bakrfatehy@yahoo.com.

Acknowledgements

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Amer, F. A.-K., Hammouda, M., El-Ahl, A.-A. S. & Abdel-Wahab, B. F. (2008). J. Heterocycl. Chem. 45, 1549–1569. CrossRef CAS Google Scholar
Amer, F. A.-K., Hammouda, M., El-Ahl, A. A. S. & Abdel-Wahab, B. F. (2009). Synth. Commun. 39, 416–425. Web of Science CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 3| March 2013| Page o437

doi:10.1107/S1600536813004893

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

4-Di­methyl­amino-1-(4-meth­­oxy­phen­yl)-2,5-dioxo-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-Dimethylamino-1-(4-methoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile