(E)-Ethyl 2-cyano-3-[5-nitro-2-(pyrrolidin-1-yl)phen-yl]acrylate.

The title compound, C(16)H(17)N(3)O(4), was prepared by the reaction of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde and ethyl cyano-acetate. The mol-ecular structure adopts an E conformation with respect to the C=C double bond. The five-membered ring has a half-chair conformation, with puckering parameters Q(2)= 0.399 (2) Å and ϕ = 93.1 (3)°. In the crystal, inversion dimers , linked by pairs of C-H⋯O inter-actions, are further connected through C-H⋯N hydrogen bonds. Weak slipped π-π inter-actions occur between symmetry-related benzene rings [centroid-centroid distance = 3.785 (1)Å].

Related literature

For related structures, see: Yapo et al. (2010 ▶); Zhang et al. (2009a ▶,b ▶). For reference bond lengths, see: Allen (2002 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H17N3O4

M = 315.33

Triclinic,

a = 8.4137 (3) Å

b = 9.9517 (4) Å

c = 10.3731 (5) Å

α = 73.065 (1)°

β = 71.388 (2)°

γ = 72.523 (4)°

V = 766.56 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 223 K

0.15 × 0.05 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

12261 measured reflections

3925 independent reflections

2436 reflections with I > 3σ(I)

R int = 0.04

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.098

S = 1.01

2436 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033374/dn2594sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033374/dn2594Isup2.hkl

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

C16H17N3O4	Z = 2
Mr = 315.33	F(000) = 332
Triclinic, P1	Dx = 1.366 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4137 (3) Å	Cell parameters from 12261 reflections
b = 9.9517 (4) Å	θ = 4–29°
c = 10.3731 (5) Å	µ = 0.10 mm−1
α = 73.065 (1)°	T = 223 K
β = 71.388 (2)°	Prism, yellow
γ = 72.523 (4)°	0.15 × 0.05 × 0.05 mm
V = 766.56 (6) Å3

Nonius KappaCCD diffractometer	Rint = 0.04
graphite	θmax = 29.1°, θmin = 2.1°
φ & ω scans	h = 0→11
12261 measured reflections	k = −12→13
3925 independent reflections	l = −12→14
2436 reflections with I > 3σ(I)

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(F2) + (0.04P)2 + 0.41P] where P = [max(Fo2,0) + 2Fc2]/3
S = 1.00	(Δ/σ)max = 0.0002
2436 reflections	Δρmax = 0.29 e Å−3
208 parameters	Δρmin = −0.19 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
O4	0.24506 (16)	0.75552 (14)	0.34637 (12)	0.0392
C6	0.6744 (2)	0.54044 (17)	0.08814 (16)	0.0272
O3	0.38346 (18)	0.74040 (16)	0.50501 (13)	0.0501
N1	0.58761 (18)	0.70320 (15)	−0.12042 (14)	0.0318
C11	0.5357 (2)	0.61576 (17)	0.18686 (16)	0.0288
C10	0.8072 (2)	0.48737 (19)	−0.14342 (18)	0.0349
O2	1.03617 (19)	0.19215 (16)	0.22812 (15)	0.0536
C14	0.3815 (2)	0.71447 (18)	0.39891 (17)	0.0335
C5	0.6844 (2)	0.58161 (18)	−0.05898 (16)	0.0281
C7	0.7910 (2)	0.41913 (18)	0.13881 (17)	0.0302
C8	0.9117 (2)	0.33592 (18)	0.05070 (18)	0.0323
N2	1.0334 (2)	0.21267 (17)	0.10625 (17)	0.0405
C12	0.5355 (2)	0.63394 (17)	0.31088 (16)	0.0295
O1	1.1330 (2)	0.13387 (17)	0.02781 (17)	0.0640
C13	0.6834 (2)	0.5867 (2)	0.36710 (18)	0.0355
N3	0.7983 (2)	0.5498 (2)	0.41549 (19)	0.0528
C9	0.9177 (2)	0.3684 (2)	−0.09019 (18)	0.0361
C1	0.6073 (3)	0.7384 (2)	−0.27297 (18)	0.0420
C4	0.4900 (2)	0.83167 (19)	−0.06191 (18)	0.0374
C16	−0.0507 (3)	0.8668 (2)	0.3594 (2)	0.0538
C15	0.0917 (3)	0.8417 (3)	0.4249 (2)	0.0524
C2	0.4880 (3)	0.8854 (2)	−0.2995 (2)	0.0520
C3	0.4940 (3)	0.9553 (2)	−0.18931 (19)	0.0458
H111	0.4299	0.6579	0.1601	0.0408*
H101	0.8112	0.5097	−0.2402	0.0501*
H71	0.7850	0.3922	0.2355	0.0416*
H91	1.0005	0.3059	−0.1485	0.0499*
H11	0.7291	0.7413	−0.3221	0.0611*
H12	0.5771	0.6646	−0.3001	0.0612*
H41	0.5454	0.8431	0.0025	0.0516*
H42	0.3687	0.8243	−0.0126	0.0529*
H161	−0.1516	0.9310	0.4046	0.0975*
H162	−0.0169	0.9098	0.2594	0.0977*
H163	−0.0794	0.7744	0.3742	0.0981*
H151	0.1190	0.9366	0.4202	0.0740*
H152	0.0663	0.7875	0.5221	0.0730*
H21	0.5289	0.9403	−0.3927	0.0751*
H22	0.3698	0.8790	−0.2855	0.0754*
H31	0.6032	0.9898	−0.2180	0.0663*
H32	0.3939	1.0346	−0.1743	0.0659*

	U11	U22	U33	U12	U13	U23
O4	0.0392 (7)	0.0457 (8)	0.0277 (6)	0.0026 (6)	−0.0057 (5)	−0.0162 (5)
C6	0.0280 (8)	0.0315 (9)	0.0230 (8)	−0.0089 (7)	−0.0040 (6)	−0.0078 (6)
O3	0.0563 (9)	0.0652 (10)	0.0332 (7)	−0.0074 (7)	−0.0099 (6)	−0.0257 (7)
N1	0.0394 (8)	0.0349 (8)	0.0223 (7)	−0.0071 (6)	−0.0101 (6)	−0.0070 (6)
C11	0.0311 (8)	0.0297 (9)	0.0234 (8)	−0.0071 (7)	−0.0044 (6)	−0.0054 (6)
C10	0.0393 (10)	0.0416 (10)	0.0250 (8)	−0.0098 (8)	−0.0041 (7)	−0.0132 (7)
O2	0.0579 (9)	0.0499 (9)	0.0435 (8)	0.0042 (7)	−0.0192 (7)	−0.0063 (6)
C14	0.0419 (10)	0.0331 (9)	0.0239 (8)	−0.0076 (7)	−0.0058 (7)	−0.0076 (7)
C5	0.0286 (8)	0.0332 (9)	0.0254 (8)	−0.0107 (7)	−0.0053 (6)	−0.0085 (7)
C7	0.0320 (9)	0.0330 (9)	0.0259 (8)	−0.0091 (7)	−0.0056 (7)	−0.0073 (7)
C8	0.0298 (9)	0.0312 (9)	0.0349 (9)	−0.0063 (7)	−0.0060 (7)	−0.0091 (7)
N2	0.0365 (9)	0.0372 (9)	0.0431 (9)	−0.0042 (7)	−0.0065 (7)	−0.0099 (7)
C12	0.0349 (9)	0.0290 (8)	0.0238 (8)	−0.0086 (7)	−0.0063 (7)	−0.0045 (6)
O1	0.0590 (9)	0.0562 (10)	0.0616 (10)	0.0174 (8)	−0.0105 (8)	−0.0274 (8)
C13	0.0427 (10)	0.0390 (10)	0.0266 (9)	−0.0133 (8)	−0.0060 (8)	−0.0086 (7)
N3	0.0521 (11)	0.0654 (12)	0.0484 (10)	−0.0155 (9)	−0.0213 (9)	−0.0120 (9)
C9	0.0359 (10)	0.0375 (10)	0.0345 (9)	−0.0089 (8)	−0.0015 (7)	−0.0149 (8)
C1	0.0566 (12)	0.0467 (11)	0.0233 (9)	−0.0082 (9)	−0.0149 (8)	−0.0069 (8)
C4	0.0435 (10)	0.0360 (10)	0.0300 (9)	−0.0026 (8)	−0.0103 (8)	−0.0090 (7)
C16	0.0431 (11)	0.0587 (14)	0.0599 (14)	−0.0028 (10)	−0.0097 (10)	−0.0260 (11)
C15	0.0436 (12)	0.0621 (14)	0.0447 (12)	0.0086 (10)	−0.0054 (9)	−0.0295 (10)
C2	0.0677 (14)	0.0514 (12)	0.0346 (10)	−0.0045 (10)	−0.0237 (10)	−0.0036 (9)
C3	0.0582 (13)	0.0381 (11)	0.0362 (10)	−0.0049 (9)	−0.0159 (9)	−0.0027 (8)

O4—C14	1.330 (2)	C12—C13	1.436 (2)
O4—C15	1.462 (2)	C13—N3	1.145 (2)
C6—C11	1.460 (2)	C9—H91	0.963
C6—C5	1.442 (2)	C1—C2	1.511 (3)
C6—C7	1.394 (2)	C1—H11	0.993
O3—C14	1.207 (2)	C1—H12	0.982
N1—C5	1.350 (2)	C4—C3	1.520 (3)
N1—C1	1.483 (2)	C4—H41	0.976
N1—C4	1.477 (2)	C4—H42	0.999
C11—C12	1.350 (2)	C16—C15	1.483 (3)
C11—H111	0.955	C16—H161	0.971
C10—C5	1.426 (2)	C16—H162	0.983
C10—C9	1.363 (2)	C16—H163	0.977
C10—H101	0.955	C15—H151	1.021
O2—N2	1.227 (2)	C15—H152	0.984
C14—C12	1.484 (2)	C2—C3	1.521 (3)
C7—C8	1.377 (2)	C2—H21	0.972
C7—H71	0.948	C2—H22	0.977
C8—N2	1.448 (2)	C3—H31	1.003
C8—C9	1.389 (2)	C3—H32	0.972
N2—O1	1.233 (2)
C14—O4—C15	114.97 (14)	N1—C1—H11	109.3
C11—C6—C5	121.29 (14)	C2—C1—H11	111.6
C11—C6—C7	119.04 (14)	N1—C1—H12	110.4
C5—C6—C7	119.46 (14)	C2—C1—H12	113.0
C5—N1—C1	120.85 (14)	H11—C1—H12	108.5
C5—N1—C4	127.13 (13)	N1—C4—C3	103.67 (14)
C1—N1—C4	110.08 (13)	N1—C4—H41	110.4
C6—C11—C12	129.25 (16)	C3—C4—H41	111.7
C6—C11—H111	115.4	N1—C4—H42	110.9
C12—C11—H111	115.3	C3—C4—H42	110.4
C5—C10—C9	122.08 (16)	H41—C4—H42	109.6
C5—C10—H101	118.2	C15—C16—H161	109.4
C9—C10—H101	119.7	C15—C16—H162	110.6
O4—C14—O3	124.77 (16)	H161—C16—H162	109.5
O4—C14—C12	112.45 (14)	C15—C16—H163	108.3
O3—C14—C12	122.77 (16)	H161—C16—H163	108.3
C6—C5—C10	116.84 (15)	H162—C16—H163	110.7
C6—C5—N1	124.27 (15)	C16—C15—O4	107.71 (16)
C10—C5—N1	118.89 (15)	C16—C15—H151	111.3
C6—C7—C8	120.77 (15)	O4—C15—H151	107.9
C6—C7—H71	119.6	C16—C15—H152	111.9
C8—C7—H71	119.6	O4—C15—H152	107.8
C7—C8—N2	119.31 (15)	H151—C15—H152	110.0
C7—C8—C9	120.95 (16)	C1—C2—C3	103.20 (15)
N2—C8—C9	119.74 (15)	C1—C2—H21	111.2
C8—N2—O2	119.06 (15)	C3—C2—H21	111.1
C8—N2—O1	118.37 (16)	C1—C2—H22	112.1
O2—N2—O1	122.55 (16)	C3—C2—H22	109.2
C14—C12—C11	122.22 (15)	H21—C2—H22	109.9
C14—C12—C13	113.25 (14)	C2—C3—C4	102.37 (16)
C11—C12—C13	124.43 (16)	C2—C3—H31	110.2
C12—C13—N3	178.06 (19)	C4—C3—H31	111.5
C8—C9—C10	119.72 (16)	C2—C3—H32	110.2
C8—C9—H91	119.1	C4—C3—H32	111.6
C10—C9—H91	121.2	H31—C3—H32	110.7
N1—C1—C2	103.93 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H152···O2i	0.98	2.50	3.356 (2)	145
C16—H163···N3ii	0.98	2.60	3.574 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H152⋯O2i	0.98	2.50	3.356 (2)	145
C16—H163⋯N3ii	0.98	2.60	3.574 (3)	172

Symmetry codes: (i) ; (ii) .