4-[(Dimethyl-amino)methyl-idene]-2-(4-nitro-phen-yl)-1,3-oxazol-5(4H)-one.

The title mol-ecule, C(12)H(11)N(3)O(4), is essentially planar, the r.m.s. deviation for all non-H atoms being 0.068 Å. An intra-molecular C-H⋯N hydrogen bond occurs. The crystal packing is dominated by π-π inter-actions [shortest centroid-centroid distance = 3.6312 (16) Å], which lead to supra-molecular chains that are linked into a three-dimensional network via C-H⋯O contacts. The crystal was found to be a non-merohedral twin (twin law -1 0 0/0 -1 0/ 0.784 0 1), the fractional contribution of the minor component being approx-imately 22%.

Related literature

For the synthesis, synthetic uses and properties of 4-(N,N-di­methyl­amino­n class="Chemical">methyl­ene)-2-aryl-2-oxazolin-5-one derivatives, see: Singh & Singh (1994 ▶, 2008 ▶); Takahashi & Izawa (2005 ▶); Singh et al. (1994 ▶); Kmetic & Stanovnik (1995 ▶). For the Vilsmeier–Haack reaction, see: Meth-Cohn & Stanforth (1991 ▶). For related structures, see Vasuki et al. (2002 ▶); Vijayalakshmi et al. (1998 ▶). For the treatment of twinned diffraction data, see: Spek (2009 ▶).

Experimental

Crystal data

C12H11N3O4

M = 261.24

Monoclinic,

a = 9.5313 (2) Å

b = 9.5204 (3) Å

c = 13.0349 (4) Å

β = 106.661 (2)°

V = 1133.15 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 120 K

0.42 × 0.38 × 0.22 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.661, T max = 1.000

14210 measured reflections

2581 independent reflections

2030 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.220

S = 1.19

2581 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.30 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018635/ez2209sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018635/ez2209Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H11N3O4	F(000) = 544
Mr = 261.24	Dx = 1.531 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2714 reflections
a = 9.5313 (2) Å	θ = 2.9–27.5°
b = 9.5204 (3) Å	µ = 0.12 mm−1
c = 13.0349 (4) Å	T = 120 K
β = 106.661 (2)°	Block, red
V = 1133.15 (6) Å3	0.42 × 0.38 × 0.22 mm
Z = 4

Nonius KappaCCD area-detector diffractometer	2581 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2030 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.071
Detector resolution: 9.091 pixels mm-1	θmax = 27.4°, θmin = 3.1°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −12→11
Tmin = 0.661, Tmax = 1.000	l = −16→16
14210 measured reflections

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.220	w = 1/[σ2(Fo2) + (0.0936P)2 + 1.6594P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max = 0.001
2581 reflections	Δρmax = 0.33 e Å−3
176 parameters	Δρmin = −0.30 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: 0.018 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2σ(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.

	x	y	z	Uiso*/Ueq
O1	0.3806 (2)	0.5986 (2)	0.33548 (17)	0.0197 (5)
O2	0.2556 (3)	0.4481 (2)	0.20576 (17)	0.0239 (6)
O3	0.8419 (3)	1.1001 (3)	0.6327 (2)	0.0324 (6)
O4	0.7443 (3)	1.0746 (3)	0.76142 (19)	0.0307 (6)
N1	0.2875 (3)	0.5457 (3)	0.4711 (2)	0.0180 (6)
N2	0.0528 (3)	0.3059 (3)	0.4441 (2)	0.0203 (6)
N3	0.7556 (3)	1.0430 (3)	0.6733 (2)	0.0209 (6)
C1	0.3786 (3)	0.6220 (3)	0.4393 (2)	0.0166 (6)
C2	0.2186 (3)	0.4617 (3)	0.3831 (2)	0.0179 (6)
C3	0.2761 (3)	0.4921 (3)	0.2958 (2)	0.0195 (7)
C4	0.1130 (3)	0.3590 (3)	0.3735 (2)	0.0189 (7)
H4	0.0778	0.3199	0.3038	0.023*
C5	0.0939 (4)	0.3462 (4)	0.5569 (3)	0.0237 (7)
H5A	0.1378	0.2655	0.6012	0.036*
H5B	0.0066	0.3768	0.5761	0.036*
H5C	0.1649	0.4233	0.5691	0.036*
C6	−0.0548 (4)	0.1947 (4)	0.4138 (3)	0.0284 (8)
H6A	−0.0780	0.1778	0.3366	0.043*
H6B	−0.1440	0.2223	0.4317	0.043*
H6C	−0.0152	0.1086	0.4526	0.043*
C7	0.4765 (3)	0.7290 (3)	0.4994 (2)	0.0168 (6)
C8	0.4797 (3)	0.7571 (3)	0.6051 (2)	0.0184 (6)
H8	0.4184	0.7056	0.6375	0.022*
C9	0.5715 (3)	0.8590 (3)	0.6624 (2)	0.0185 (6)
H9	0.5735	0.8794	0.7342	0.022*
C10	0.6608 (3)	0.9314 (3)	0.6135 (2)	0.0178 (6)
C11	0.6608 (3)	0.9058 (3)	0.5089 (2)	0.0173 (6)
H11	0.7231	0.9571	0.4772	0.021*
C12	0.5676 (3)	0.8035 (3)	0.4519 (2)	0.0175 (6)
H12	0.5655	0.7838	0.3800	0.021*

	U11	U22	U33	U12	U13	U23
O1	0.0239 (12)	0.0203 (11)	0.0177 (11)	−0.0022 (9)	0.0105 (9)	−0.0010 (8)
O2	0.0307 (13)	0.0242 (12)	0.0187 (11)	−0.0017 (10)	0.0100 (10)	−0.0029 (9)
O3	0.0323 (14)	0.0382 (15)	0.0291 (13)	−0.0147 (12)	0.0127 (11)	−0.0044 (11)
O4	0.0397 (15)	0.0328 (14)	0.0219 (12)	−0.0061 (12)	0.0125 (11)	−0.0075 (10)
N1	0.0195 (13)	0.0171 (12)	0.0183 (13)	0.0003 (10)	0.0067 (10)	0.0004 (10)
N2	0.0209 (13)	0.0163 (13)	0.0248 (13)	0.0015 (11)	0.0082 (11)	0.0025 (10)
N3	0.0219 (13)	0.0210 (13)	0.0195 (13)	0.0017 (12)	0.0056 (11)	0.0024 (11)
C1	0.0193 (14)	0.0179 (14)	0.0143 (13)	0.0046 (12)	0.0073 (11)	0.0029 (11)
C2	0.0198 (15)	0.0172 (14)	0.0173 (14)	0.0032 (12)	0.0065 (12)	0.0009 (11)
C3	0.0218 (15)	0.0165 (14)	0.0207 (15)	0.0022 (12)	0.0068 (12)	0.0030 (12)
C4	0.0222 (16)	0.0156 (14)	0.0198 (15)	0.0042 (12)	0.0076 (12)	0.0024 (11)
C5	0.0270 (17)	0.0235 (16)	0.0246 (16)	0.0024 (14)	0.0136 (14)	0.0033 (13)
C6	0.0247 (17)	0.0210 (16)	0.039 (2)	−0.0050 (14)	0.0077 (15)	0.0059 (14)
C7	0.0182 (15)	0.0145 (14)	0.0185 (14)	0.0035 (12)	0.0062 (12)	0.0022 (11)
C8	0.0201 (15)	0.0188 (15)	0.0184 (14)	0.0018 (12)	0.0089 (12)	0.0040 (12)
C9	0.0215 (15)	0.0193 (15)	0.0158 (13)	0.0052 (13)	0.0070 (12)	0.0030 (12)
C10	0.0174 (14)	0.0152 (14)	0.0198 (15)	0.0025 (12)	0.0036 (12)	−0.0005 (11)
C11	0.0180 (14)	0.0175 (14)	0.0178 (14)	0.0023 (12)	0.0073 (11)	0.0035 (11)
C12	0.0193 (14)	0.0184 (14)	0.0169 (14)	0.0029 (12)	0.0086 (12)	0.0014 (11)

O1—C1	1.377 (3)	C5—H5B	0.9800
O1—C3	1.411 (4)	C5—H5C	0.9800
O2—C3	1.209 (4)	C6—H6A	0.9800
O3—N3	1.226 (4)	C6—H6B	0.9800
O4—N3	1.222 (4)	C6—H6C	0.9800
N1—C1	1.289 (4)	C7—C8	1.394 (4)
N1—C2	1.398 (4)	C7—C12	1.396 (4)
N2—C4	1.317 (4)	C8—C9	1.375 (4)
N2—C6	1.448 (4)	C8—H8	0.9500
N2—C5	1.460 (4)	C9—C10	1.385 (4)
N3—C10	1.466 (4)	C9—H9	0.9500
C1—C7	1.450 (4)	C10—C11	1.385 (4)
C2—C4	1.382 (5)	C11—C12	1.383 (4)
C2—C3	1.428 (4)	C11—H11	0.9500
C4—H4	0.9500	C12—H12	0.9500
C5—H5A	0.9800
C1—O1—C3	105.6 (2)	H5B—C5—H5C	109.5
C1—N1—C2	105.0 (2)	N2—C6—H6A	109.5
C4—N2—C6	120.5 (3)	N2—C6—H6B	109.5
C4—N2—C5	123.9 (3)	H6A—C6—H6B	109.5
C6—N2—C5	115.5 (3)	N2—C6—H6C	109.5
O4—N3—O3	123.2 (3)	H6A—C6—H6C	109.5
O4—N3—C10	118.1 (3)	H6B—C6—H6C	109.5
O3—N3—C10	118.7 (3)	C8—C7—C12	120.0 (3)
N1—C1—O1	115.2 (3)	C8—C7—C1	119.8 (3)
N1—C1—C7	127.6 (3)	C12—C7—C1	120.2 (3)
O1—C1—C7	117.2 (3)	C9—C8—C7	120.2 (3)
C4—C2—N1	129.6 (3)	C9—C8—H8	119.9
C4—C2—C3	120.5 (3)	C7—C8—H8	119.9
N1—C2—C3	109.9 (3)	C8—C9—C10	118.7 (3)
O2—C3—O1	120.4 (3)	C8—C9—H9	120.7
O2—C3—C2	135.4 (3)	C10—C9—H9	120.7
O1—C3—C2	104.3 (2)	C11—C10—C9	122.7 (3)
N2—C4—C2	131.3 (3)	C11—C10—N3	118.5 (3)
N2—C4—H4	114.4	C9—C10—N3	118.8 (3)
C2—C4—H4	114.4	C12—C11—C10	118.1 (3)
N2—C5—H5A	109.5	C12—C11—H11	120.9
N2—C5—H5B	109.5	C10—C11—H11	120.9
H5A—C5—H5B	109.5	C11—C12—C7	120.4 (3)
N2—C5—H5C	109.5	C11—C12—H12	119.8
H5A—C5—H5C	109.5	C7—C12—H12	119.8
C2—N1—C1—O1	−0.3 (3)	O1—C1—C7—C8	−179.8 (3)
C2—N1—C1—C7	179.1 (3)	N1—C1—C7—C12	−179.3 (3)
C3—O1—C1—N1	−0.1 (3)	O1—C1—C7—C12	0.1 (4)
C3—O1—C1—C7	−179.5 (3)	C12—C7—C8—C9	0.6 (5)
C1—N1—C2—C4	178.8 (3)	C1—C7—C8—C9	−179.5 (3)
C1—N1—C2—C3	0.5 (3)	C7—C8—C9—C10	−0.7 (5)
C1—O1—C3—O2	−178.9 (3)	C8—C9—C10—C11	0.4 (5)
C1—O1—C3—C2	0.4 (3)	C8—C9—C10—N3	178.2 (3)
C4—C2—C3—O2	0.1 (6)	O4—N3—C10—C11	172.7 (3)
N1—C2—C3—O2	178.6 (4)	O3—N3—C10—C11	−7.1 (4)
C4—C2—C3—O1	−179.1 (3)	O4—N3—C10—C9	−5.1 (4)
N1—C2—C3—O1	−0.6 (3)	O3—N3—C10—C9	175.0 (3)
C6—N2—C4—C2	−178.4 (3)	C9—C10—C11—C12	−0.1 (5)
C5—N2—C4—C2	−2.4 (5)	N3—C10—C11—C12	−177.9 (3)
N1—C2—C4—N2	−3.9 (6)	C10—C11—C12—C7	0.1 (4)
C3—C2—C4—N2	174.2 (3)	C8—C7—C12—C11	−0.3 (4)
N1—C1—C7—C8	0.9 (5)	C1—C7—C12—C11	179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5c···N1	0.98	2.28	3.074 (5)	137
C5—H5a···O2i	0.98	2.53	3.504 (4)	177
C5—H5c···O4ii	0.98	2.57	3.259 (5)	127
C9—H9···O1iii	0.95	2.56	3.304 (4)	135
C11—H11···O2iv	0.95	2.45	3.144 (4)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5c⋯N1	0.98	2.28	3.074 (5)	137
C5—H5a⋯O2i	0.98	2.53	3.504 (4)	177
C5—H5c⋯O4ii	0.98	2.57	3.259 (5)	127
C9—H9⋯O1iii	0.95	2.56	3.304 (4)	135
C11—H11⋯O2iv	0.95	2.45	3.144 (4)	130

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .