Diethyl 2-(2-nitro-benzyl-idene)malonate.

In the title compound, C(14)H(15)NO(6), the ethoxy-carbonyl groups adopt extended conformations. In the crystal, mol-ecules are linked into centrosymmetric dimers via pairs of C-H⋯O hydrogen bonds with a R(2) (2)(20) motif.

Related literature

For biological activity of nitro­gen-containing building blocks derived from α-methyl­ene-β-hydr­oxy esters, see: Singh & Batra (2008 ▶); Masson et al. (2007 ▶); Basavaiah et al. (2003 ▶); Youngme et al. (2007 ▶); Ma et al. (2005 ▶); Soldatov et al. (2003 ▶); Hinckley (1969 ▶).

Experimental

Crystal data

C14H15NO6

M = 293.27

Triclinic,

a = 7.8410 (2) Å

b = 8.5571 (2) Å

c = 12.3533 (4) Å

α = 80.866 (2)°

β = 75.037 (1)°

γ = 64.402 (1)°

V = 721.10 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.21 × 0.19 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.982

19570 measured reflections

4226 independent reflections

3259 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.145

S = 1.06

4226 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032668/bt5022sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032668/bt5022Isup2.hkl

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

C14H15NO6	Z = 2
Mr = 293.27	F(000) = 308
Triclinic, P1	Dx = 1.351 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8410 (2) Å	Cell parameters from 4226 reflections
b = 8.5571 (2) Å	θ = 1.7–30.7°
c = 12.3533 (4) Å	µ = 0.11 mm−1
α = 80.866 (2)°	T = 293 K
β = 75.037 (1)°	Block, colourless
γ = 64.402 (1)°	0.21 × 0.19 × 0.17 mm
V = 721.10 (3) Å3

Bruker Kappa APEXII CCD diffractometer	4226 independent reflections
Radiation source: fine-focus sealed tube	3259 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 30.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→11
Tmin = 0.978, Tmax = 0.982	k = −11→12
19570 measured reflections	l = −17→17

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) = 0.145	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0732P)2 + 0.1321P] where P = (Fo2 + 2Fc2)/3
4226 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.32734 (17)	0.26054 (16)	0.00483 (10)	0.0324 (3)
C2	0.4208 (2)	0.18112 (18)	−0.09512 (11)	0.0393 (3)
H2	0.3530	0.1563	−0.1367	0.047*
C3	0.6156 (2)	0.1390 (2)	−0.13275 (12)	0.0445 (3)
H3	0.6808	0.0854	−0.2002	0.053*
C4	0.7138 (2)	0.1765 (2)	−0.07003 (12)	0.0444 (3)
H4	0.8458	0.1469	−0.0951	0.053*
C5	0.61807 (19)	0.25790 (18)	0.02979 (11)	0.0380 (3)
H5	0.6867	0.2834	0.0704	0.046*
C6	0.42104 (17)	0.30233 (16)	0.07069 (10)	0.0307 (2)
C7	0.32275 (18)	0.40052 (17)	0.17243 (11)	0.0335 (3)
H7	0.2096	0.4996	0.1694	0.040*
C8	0.38277 (18)	0.35895 (16)	0.26840 (10)	0.0322 (3)
C9	0.54181 (19)	0.18778 (16)	0.28991 (10)	0.0339 (3)
C10	0.8427 (2)	0.0493 (2)	0.34618 (14)	0.0517 (4)
H10A	0.9576	0.0709	0.3360	0.062*
H10B	0.8725	−0.0413	0.2972	0.062*
C11	0.7894 (3)	−0.0099 (2)	0.46438 (15)	0.0570 (4)
H11A	0.7533	0.0818	0.5126	0.086*
H11B	0.8980	−0.1092	0.4840	0.086*
H11C	0.6824	−0.0408	0.4730	0.086*
C12	0.27995 (18)	0.48151 (17)	0.36030 (11)	0.0350 (3)
C13	0.2334 (2)	0.51216 (19)	0.55376 (11)	0.0432 (3)
H13A	0.0935	0.5618	0.5646	0.052*
H13B	0.2752	0.6061	0.5419	0.052*
C14	0.2947 (3)	0.4002 (2)	0.65347 (13)	0.0581 (4)
H14A	0.2440	0.3131	0.6678	0.087*
H14B	0.2462	0.4697	0.7174	0.087*
H14C	0.4334	0.3452	0.6397	0.087*
N	0.12284 (17)	0.29396 (16)	0.04462 (12)	0.0446 (3)
O1	0.03150 (19)	0.3042 (2)	−0.02475 (13)	0.0753 (4)
O2	0.05294 (17)	0.30788 (19)	0.14427 (11)	0.0651 (4)
O3	0.53708 (18)	0.05173 (13)	0.28408 (10)	0.0536 (3)
O4	0.17045 (18)	0.63004 (14)	0.34780 (9)	0.0564 (3)
O5	0.32173 (14)	0.40462 (12)	0.45770 (8)	0.0394 (2)
O6	0.68593 (13)	0.20702 (12)	0.31542 (9)	0.0417 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0360 (6)	0.0334 (6)	0.0324 (6)	−0.0158 (5)	−0.0140 (5)	0.0017 (5)
C2	0.0546 (8)	0.0390 (7)	0.0318 (6)	−0.0213 (6)	−0.0185 (6)	−0.0007 (5)
C3	0.0560 (8)	0.0465 (8)	0.0301 (7)	−0.0220 (7)	−0.0034 (6)	−0.0068 (6)
C4	0.0409 (7)	0.0516 (8)	0.0402 (7)	−0.0221 (6)	0.0000 (6)	−0.0065 (6)
C5	0.0384 (6)	0.0467 (7)	0.0357 (7)	−0.0220 (6)	−0.0098 (5)	−0.0037 (6)
C6	0.0364 (6)	0.0320 (6)	0.0264 (6)	−0.0150 (5)	−0.0105 (4)	0.0001 (4)
C7	0.0345 (6)	0.0339 (6)	0.0331 (6)	−0.0130 (5)	−0.0095 (5)	−0.0037 (5)
C8	0.0374 (6)	0.0303 (6)	0.0299 (6)	−0.0130 (5)	−0.0083 (5)	−0.0052 (5)
C9	0.0445 (6)	0.0313 (6)	0.0249 (6)	−0.0119 (5)	−0.0099 (5)	−0.0057 (4)
C10	0.0354 (7)	0.0476 (8)	0.0584 (10)	−0.0017 (6)	−0.0121 (6)	−0.0072 (7)
C11	0.0533 (9)	0.0496 (9)	0.0595 (10)	−0.0091 (7)	−0.0232 (7)	0.0035 (8)
C12	0.0382 (6)	0.0330 (6)	0.0333 (6)	−0.0120 (5)	−0.0089 (5)	−0.0059 (5)
C13	0.0523 (8)	0.0386 (7)	0.0336 (7)	−0.0118 (6)	−0.0064 (6)	−0.0129 (6)
C14	0.0844 (12)	0.0509 (9)	0.0335 (8)	−0.0210 (8)	−0.0129 (8)	−0.0067 (7)
N	0.0378 (6)	0.0457 (7)	0.0561 (8)	−0.0183 (5)	−0.0164 (5)	−0.0047 (6)
O1	0.0558 (7)	0.1031 (11)	0.0868 (10)	−0.0357 (7)	−0.0377 (7)	−0.0131 (8)
O2	0.0455 (6)	0.0896 (10)	0.0628 (8)	−0.0328 (6)	0.0022 (5)	−0.0185 (7)
O3	0.0800 (8)	0.0325 (5)	0.0580 (7)	−0.0194 (5)	−0.0361 (6)	−0.0042 (5)
O4	0.0665 (7)	0.0376 (6)	0.0441 (6)	0.0029 (5)	−0.0168 (5)	−0.0086 (5)
O5	0.0511 (5)	0.0328 (5)	0.0292 (5)	−0.0096 (4)	−0.0096 (4)	−0.0086 (4)
O6	0.0364 (5)	0.0370 (5)	0.0497 (6)	−0.0103 (4)	−0.0137 (4)	−0.0033 (4)

C1—C2	1.3756 (19)	C10—O6	1.4566 (17)
C1—C6	1.3991 (16)	C10—C11	1.482 (2)
C1—N	1.4615 (17)	C10—H10A	0.9700
C2—C3	1.375 (2)	C10—H10B	0.9700
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.377 (2)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—C5	1.383 (2)	C12—O4	1.1998 (16)
C4—H4	0.9300	C12—O5	1.3244 (16)
C5—C6	1.3917 (17)	C13—O5	1.4512 (16)
C5—H5	0.9300	C13—C14	1.483 (2)
C6—C7	1.4680 (17)	C13—H13A	0.9700
C7—C8	1.3278 (17)	C13—H13B	0.9700
C7—H7	0.9300	C14—H14A	0.9600
C8—C12	1.4878 (17)	C14—H14B	0.9600
C8—C9	1.4967 (17)	C14—H14C	0.9600
C9—O3	1.1947 (16)	N—O2	1.2132 (18)
C9—O6	1.3283 (16)	N—O1	1.2222 (17)
C2—C1—C6	123.07 (12)	O6—C10—H10B	109.4
C2—C1—N	117.21 (11)	C11—C10—H10B	109.4
C6—C1—N	119.66 (12)	H10A—C10—H10B	108.0
C3—C2—C1	119.15 (12)	C10—C11—H11A	109.5
C3—C2—H2	120.4	C10—C11—H11B	109.5
C1—C2—H2	120.4	H11A—C11—H11B	109.5
C4—C3—C2	119.66 (13)	C10—C11—H11C	109.5
C4—C3—H3	120.2	H11A—C11—H11C	109.5
C2—C3—H3	120.2	H11B—C11—H11C	109.5
C3—C4—C5	120.72 (13)	O4—C12—O5	124.51 (12)
C3—C4—H4	119.6	O4—C12—C8	124.15 (12)
C5—C4—H4	119.6	O5—C12—C8	111.33 (10)
C4—C5—C6	121.29 (12)	O5—C13—C14	107.61 (12)
C4—C5—H5	119.4	O5—C13—H13A	110.2
C6—C5—H5	119.4	C14—C13—H13A	110.2
C5—C6—C1	116.11 (11)	O5—C13—H13B	110.2
C5—C6—C7	119.28 (11)	C14—C13—H13B	110.2
C1—C6—C7	124.41 (11)	H13A—C13—H13B	108.5
C8—C7—C6	125.13 (11)	C13—C14—H14A	109.5
C8—C7—H7	117.4	C13—C14—H14B	109.5
C6—C7—H7	117.4	H14A—C14—H14B	109.5
C7—C8—C12	118.91 (11)	C13—C14—H14C	109.5
C7—C8—C9	122.12 (11)	H14A—C14—H14C	109.5
C12—C8—C9	118.84 (10)	H14B—C14—H14C	109.5
O3—C9—O6	125.05 (12)	O2—N—O1	123.34 (13)
O3—C9—C8	123.16 (12)	O2—N—C1	118.78 (11)
O6—C9—C8	111.79 (11)	O1—N—C1	117.87 (13)
O6—C10—C11	111.16 (12)	C12—O5—C13	116.56 (10)
O6—C10—H10A	109.4	C9—O6—C10	116.65 (11)
C11—C10—H10A	109.4
C6—C1—C2—C3	0.5 (2)	C7—C8—C9—O6	123.02 (13)
N—C1—C2—C3	−176.61 (12)	C12—C8—C9—O6	−61.15 (15)
C1—C2—C3—C4	0.1 (2)	C7—C8—C12—O4	−15.0 (2)
C2—C3—C4—C5	−0.7 (2)	C9—C8—C12—O4	169.01 (14)
C3—C4—C5—C6	0.8 (2)	C7—C8—C12—O5	163.66 (12)
C4—C5—C6—C1	−0.28 (19)	C9—C8—C12—O5	−12.30 (16)
C4—C5—C6—C7	−175.29 (12)	C2—C1—N—O2	155.65 (14)
C2—C1—C6—C5	−0.36 (19)	C6—C1—N—O2	−21.53 (19)
N—C1—C6—C5	176.64 (11)	C2—C1—N—O1	−23.42 (19)
C2—C1—C6—C7	174.37 (12)	C6—C1—N—O1	159.40 (14)
N—C1—C6—C7	−8.63 (18)	O4—C12—O5—C13	−2.7 (2)
C5—C6—C7—C8	−50.59 (19)	C8—C12—O5—C13	178.64 (11)
C1—C6—C7—C8	134.84 (14)	C14—C13—O5—C12	178.49 (13)
C6—C7—C8—C12	173.32 (11)	O3—C9—O6—C10	−4.6 (2)
C6—C7—C8—C9	−10.8 (2)	C8—C9—O6—C10	175.61 (11)
C7—C8—C9—O3	−56.78 (19)	C11—C10—O6—C9	−79.96 (17)
C12—C8—C9—O3	119.05 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.93	2.47	3.1683 (18)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.93	2.47	3.1683 (18)	132

Symmetry code: (i) .