(E,E)-Methyl 2-[(3-nitrobenzylidene)-aminomethyl]-3-phenylpropenoate.

The mol-ecule of the title compound, C(18)H(16)N(2)O(4), adopts a T-shaped conformation with E stereochemistry for the imine double bond. The (3-nitro-benzyl-idene)amino fragment is almost planar, the mean planes of phenyl ring and nitro group forming a dihedral angle of 8.9 (3)°. In the 3-phenyl-acryloyl unit, the acrylic ester fragment is also almost planar, with the phenyl ring twisted by 41.44 (7)°. In the crystal, the mol-ecules are linked by C-H⋯O hydrogen-bond inter-actions into chains running parallel to [01].

Related literature

For general background to the chemistry of Morita–Baylis–Hillman adducts, see: Singh & Batra (2008 ▶); Masson et al. (2007 ▶); Basavaiah et al. (2003 ▶). For background to this study, see: Bortoluzzi et al. (2006 ▶); Fernandes et al. (2004 ▶); Sá et al. (2006 ▶, 2007 ▶, 2008 ▶). For the synthesis, see: Sá (2003 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶); and of MOGUL, see: Bruno et al. (2004 ▶).

Experimental

Crystal data

C18H16N2O4

M = 324.33

Triclinic,

a = 8.6035 (12) Å

b = 8.7829 (14) Å

c = 12.4680 (14) Å

α = 79.275 (18)°

β = 76.526 (13)°

γ = 63.158 (14)°

V = 813.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.50 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

3026 measured reflections

2883 independent reflections

2165 reflections with > 2σ (I)

R int = 0.024

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.09

2883 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: SET4 in CAD-4 Software; data reduction: HELENA (Spek, 1996 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043262/rz2278sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043262/rz2278Isup2.hkl

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

C18H16N2O4	Z = 2
Mr = 324.33	F(000) = 340
Triclinic, P1	Dx = 1.323 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.6035 (12) Å	Cell parameters from 25 reflections
b = 8.7829 (14) Å	θ = 5.3–16.7°
c = 12.4680 (14) Å	µ = 0.10 mm−1
α = 79.275 (18)°	T = 293 K
β = 76.526 (13)°	Irregular block, colorless
γ = 63.158 (14)°	0.50 × 0.30 × 0.20 mm
V = 813.9 (2) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.024
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 1.7°
graphite	h = −10→9
ω–2θ scans	k = −10→10
3026 measured reflections	l = −14→0
2883 independent reflections	3 standard reflections every 200 reflections
2165 reflections with > 2σ (I)	intensity decay: 1%

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0588P)2 + 0.1527P] where P = (Fo2 + 2Fc2)/3
2883 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.1755 (2)	0.5606 (2)	0.77725 (14)	0.0470 (4)
H1	0.1648	0.6615	0.7983	0.056*
N2	0.1722 (2)	0.55429 (18)	0.67793 (12)	0.0492 (4)
C3	0.1642 (3)	0.7065 (2)	0.60179 (15)	0.0514 (5)
H3A	0.2700	0.6741	0.5459	0.062*
H3B	0.1627	0.7908	0.6430	0.062*
C4	0.0043 (2)	0.7874 (2)	0.54518 (14)	0.0465 (4)
C5	0.0074 (2)	0.7661 (2)	0.44100 (14)	0.0488 (4)
H5	−0.0960	0.8330	0.4121	0.059*
C6	−0.1594 (3)	0.9030 (2)	0.61246 (15)	0.0515 (5)
O7	−0.1704 (2)	0.91839 (19)	0.70815 (11)	0.0734 (4)
O8	−0.29582 (18)	0.98968 (18)	0.55747 (11)	0.0639 (4)
C9	−0.4579 (3)	1.1040 (3)	0.6204 (2)	0.0796 (7)
H9A	−0.4923	1.0411	0.6855	0.119*
H9B	−0.5493	1.1532	0.5758	0.119*
H9C	−0.4398	1.1936	0.6416	0.119*
C11	0.1958 (2)	0.4135 (2)	0.86183 (14)	0.0446 (4)
C12	0.1900 (2)	0.2681 (2)	0.83818 (13)	0.0434 (4)
H12	0.1726	0.2610	0.7687	0.052*
C13	0.2104 (2)	0.1340 (2)	0.91989 (14)	0.0471 (4)
N13	0.2048 (2)	−0.01950 (19)	0.89347 (14)	0.0573 (4)
O14	0.2052 (2)	−0.03191 (17)	0.79774 (13)	0.0745 (5)
O15	0.2022 (3)	−0.13071 (19)	0.96882 (14)	0.0879 (5)
C14	0.2357 (3)	0.1386 (3)	1.02445 (15)	0.0579 (5)
H14	0.2487	0.0465	1.0780	0.069*
C15	0.2412 (3)	0.2832 (3)	1.04694 (16)	0.0625 (5)
H15	0.2582	0.2896	1.1166	0.075*
C16	0.2215 (3)	0.4193 (3)	0.96652 (15)	0.0555 (5)
H16	0.2255	0.5163	0.9829	0.067*
C21	0.1565 (2)	0.6482 (2)	0.36716 (14)	0.0465 (4)
C22	0.1946 (3)	0.7024 (2)	0.25635 (15)	0.0546 (5)
H22	0.1252	0.8133	0.2294	0.066*
C23	0.3330 (3)	0.5951 (3)	0.18584 (17)	0.0615 (5)
H23	0.3578	0.6345	0.1122	0.074*
C24	0.4353 (3)	0.4296 (3)	0.22366 (18)	0.0631 (5)
H24	0.5284	0.3567	0.1758	0.076*
C25	0.3986 (3)	0.3727 (3)	0.33283 (19)	0.0660 (6)
H25	0.4671	0.2607	0.3585	0.079*
C26	0.2610 (3)	0.4802 (2)	0.40479 (17)	0.0575 (5)
H26	0.2379	0.4405	0.4785	0.069*

	U11	U22	U33	U12	U13	U23
C1	0.0563 (11)	0.0396 (9)	0.0488 (10)	−0.0228 (8)	−0.0137 (8)	0.0000 (7)
N2	0.0628 (9)	0.0407 (8)	0.0475 (9)	−0.0251 (7)	−0.0172 (7)	0.0061 (6)
C3	0.0672 (12)	0.0433 (10)	0.0499 (10)	−0.0310 (9)	−0.0165 (9)	0.0089 (8)
C4	0.0590 (11)	0.0372 (9)	0.0456 (10)	−0.0253 (8)	−0.0114 (8)	0.0066 (7)
C5	0.0529 (10)	0.0424 (9)	0.0495 (10)	−0.0203 (8)	−0.0123 (8)	0.0039 (7)
C6	0.0668 (12)	0.0407 (9)	0.0452 (10)	−0.0263 (9)	−0.0070 (9)	0.0059 (8)
O7	0.0964 (11)	0.0643 (9)	0.0464 (8)	−0.0243 (8)	−0.0094 (7)	−0.0052 (7)
O8	0.0579 (8)	0.0640 (9)	0.0542 (8)	−0.0156 (7)	−0.0047 (6)	−0.0037 (6)
C9	0.0652 (14)	0.0729 (15)	0.0783 (16)	−0.0156 (12)	0.0041 (11)	−0.0130 (12)
C11	0.0488 (10)	0.0412 (9)	0.0426 (9)	−0.0192 (8)	−0.0077 (7)	−0.0012 (7)
C12	0.0486 (10)	0.0415 (9)	0.0377 (9)	−0.0174 (8)	−0.0083 (7)	−0.0019 (7)
C13	0.0512 (10)	0.0381 (9)	0.0462 (10)	−0.0161 (8)	−0.0066 (8)	−0.0008 (7)
N13	0.0659 (10)	0.0370 (8)	0.0624 (10)	−0.0180 (7)	−0.0122 (8)	0.0017 (7)
O14	0.1120 (13)	0.0471 (8)	0.0688 (10)	−0.0313 (8)	−0.0292 (9)	−0.0051 (7)
O15	0.1339 (15)	0.0511 (9)	0.0784 (11)	−0.0470 (10)	−0.0178 (10)	0.0146 (8)
C14	0.0723 (13)	0.0535 (11)	0.0439 (10)	−0.0271 (10)	−0.0127 (9)	0.0088 (8)
C15	0.0845 (15)	0.0690 (13)	0.0398 (10)	−0.0371 (11)	−0.0171 (10)	0.0012 (9)
C16	0.0724 (13)	0.0543 (11)	0.0467 (10)	−0.0325 (10)	−0.0109 (9)	−0.0047 (8)
C21	0.0509 (10)	0.0436 (9)	0.0493 (10)	−0.0228 (8)	−0.0130 (8)	−0.0018 (8)
C22	0.0623 (12)	0.0505 (11)	0.0479 (10)	−0.0202 (9)	−0.0164 (9)	0.0015 (8)
C23	0.0650 (12)	0.0672 (13)	0.0484 (11)	−0.0253 (11)	−0.0078 (9)	−0.0065 (9)
C24	0.0579 (12)	0.0596 (12)	0.0693 (14)	−0.0199 (10)	−0.0076 (10)	−0.0179 (10)
C25	0.0702 (13)	0.0401 (10)	0.0814 (15)	−0.0167 (10)	−0.0171 (11)	−0.0040 (10)
C26	0.0683 (12)	0.0432 (10)	0.0593 (12)	−0.0253 (9)	−0.0111 (9)	0.0034 (8)

C1—N2	1.257 (2)	C13—C14	1.381 (3)
C1—C11	1.478 (2)	C13—N13	1.470 (2)
C1—H1	0.9300	N13—O14	1.218 (2)
N2—C3	1.473 (2)	N13—O15	1.227 (2)
C3—C4	1.509 (2)	C14—C15	1.373 (3)
C3—H3A	0.9700	C14—H14	0.9300
C3—H3B	0.9700	C15—C16	1.383 (3)
C4—C5	1.339 (2)	C15—H15	0.9300
C4—C6	1.481 (3)	C16—H16	0.9300
C5—C21	1.473 (2)	C21—C22	1.389 (3)
C5—H5	0.9300	C21—C26	1.395 (3)
C6—O7	1.203 (2)	C22—C23	1.373 (3)
C6—O8	1.342 (2)	C22—H22	0.9300
O8—C9	1.445 (2)	C23—C24	1.376 (3)
C9—H9A	0.9600	C23—H23	0.9300
C9—H9B	0.9600	C24—C25	1.375 (3)
C9—H9C	0.9600	C24—H24	0.9300
C11—C16	1.387 (2)	C25—C26	1.382 (3)
C11—C12	1.388 (2)	C25—H25	0.9300
C12—C13	1.380 (2)	C26—H26	0.9300
C12—H12	0.9300
N2—C1—C11	122.48 (16)	C12—C13—N13	118.04 (16)
N2—C1—H1	118.8	C14—C13—N13	119.12 (16)
C11—C1—H1	118.8	O14—N13—O15	122.86 (17)
C1—N2—C3	116.16 (15)	O14—N13—C13	118.70 (15)
N2—C3—C4	113.24 (14)	O15—N13—C13	118.44 (17)
N2—C3—H3A	108.9	C15—C14—C13	118.01 (17)
C4—C3—H3A	108.9	C15—C14—H14	121.0
N2—C3—H3B	108.9	C13—C14—H14	121.0
C4—C3—H3B	108.9	C14—C15—C16	120.37 (18)
H3A—C3—H3B	107.7	C14—C15—H15	119.8
C5—C4—C6	121.26 (17)	C16—C15—H15	119.8
C5—C4—C3	124.23 (17)	C15—C16—C11	121.17 (18)
C6—C4—C3	114.43 (16)	C15—C16—H16	119.4
C4—C5—C21	127.15 (17)	C11—C16—H16	119.4
C4—C5—H5	116.4	C22—C21—C26	118.14 (17)
C21—C5—H5	116.4	C22—C21—C5	120.03 (16)
O7—C6—O8	122.52 (18)	C26—C21—C5	121.82 (16)
O7—C6—C4	123.31 (18)	C23—C22—C21	121.17 (18)
O8—C6—C4	114.17 (16)	C23—C22—H22	119.4
C6—O8—C9	115.78 (16)	C21—C22—H22	119.4
O8—C9—H9A	109.5	C22—C23—C24	120.28 (19)
O8—C9—H9B	109.5	C22—C23—H23	119.9
H9A—C9—H9B	109.5	C24—C23—H23	119.9
O8—C9—H9C	109.5	C25—C24—C23	119.5 (2)
H9A—C9—H9C	109.5	C25—C24—H24	120.3
H9B—C9—H9C	109.5	C23—C24—H24	120.3
C16—C11—C12	118.96 (16)	C24—C25—C26	120.70 (19)
C16—C11—C1	120.11 (16)	C24—C25—H25	119.7
C12—C11—C1	120.93 (15)	C26—C25—H25	119.7
C13—C12—C11	118.65 (16)	C25—C26—C21	120.21 (19)
C13—C12—H12	120.7	C25—C26—H26	119.9
C11—C12—H12	120.7	C21—C26—H26	119.9
C12—C13—C14	122.84 (17)
C11—C1—N2—C3	−175.74 (16)	C14—C13—N13—O14	−170.73 (18)
C1—N2—C3—C4	−121.34 (18)	C12—C13—N13—O15	−171.67 (17)
N2—C3—C4—C5	−101.1 (2)	C14—C13—N13—O15	8.4 (3)
N2—C3—C4—C6	82.07 (19)	C12—C13—C14—C15	−0.2 (3)
C6—C4—C5—C21	−175.96 (15)	N13—C13—C14—C15	179.74 (18)
C3—C4—C5—C21	7.5 (3)	C13—C14—C15—C16	0.1 (3)
C5—C4—C6—O7	175.67 (18)	C14—C15—C16—C11	0.0 (3)
C3—C4—C6—O7	−7.4 (2)	C12—C11—C16—C15	0.0 (3)
C5—C4—C6—O8	−4.2 (2)	C1—C11—C16—C15	−179.85 (18)
C3—C4—C6—O8	172.71 (14)	C4—C5—C21—C22	−138.14 (19)
O7—C6—O8—C9	0.2 (3)	C4—C5—C21—C26	42.9 (3)
C4—C6—O8—C9	−179.94 (16)	C26—C21—C22—C23	−1.1 (3)
N2—C1—C11—C16	171.68 (18)	C5—C21—C22—C23	179.90 (17)
N2—C1—C11—C12	−8.2 (3)	C21—C22—C23—C24	1.2 (3)
C16—C11—C12—C13	−0.1 (3)	C22—C23—C24—C25	−0.5 (3)
C1—C11—C12—C13	179.71 (16)	C23—C24—C25—C26	−0.3 (3)
C11—C12—C13—C14	0.3 (3)	C24—C25—C26—C21	0.4 (3)
C11—C12—C13—N13	−179.70 (15)	C22—C21—C26—C25	0.3 (3)
C12—C13—N13—O14	9.2 (3)	C5—C21—C26—C25	179.29 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O15i	0.93	2.55	3.307 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O15i	0.93	2.55	3.307 (3)	139

Symmetry code: (i) .