2-Eth-oxy-ethyl (Z)-2-cyano-3-[(N-phenyl-carbamo-yl)amino]-prop-2-enoate.

The crystal structure of the title compound, C(15)H(17)N(3)O(4), is stabilized by inter-molecular N-H⋯N hydrogen bonds. An intra-molecular N-H⋯O hydrogen bond also occurs.

Related literature

The title compound was synthesized as a possible novel herbicide. For details of the synthesis, see: Wang et al. (2004 ▶); Senda et al. (1972 ▶). For reviews of cyano­acrylate derivatives as bioactive agents, see: Zhang et al. (2008 ▶); Liu et al. (1998 ▶).

Experimental

Crystal data

C15H17N3O4

M = 303.32

Monoclinic,

a = 25.102 (7) Å

b = 12.013 (3) Å

c = 10.436 (3) Å

β = 96.248 (4)°

V = 3128.4 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 153 K

0.48 × 0.44 × 0.09 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.956, T max = 0.992

16240 measured reflections

4149 independent reflections

2994 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.116

S = 1.00

4149 reflections

208 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055000/hg5148sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055000/hg5148Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055000/hg5148Isup3.cml

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

C15H17N3O4	F(000) = 1280
Mr = 303.32	Dx = 1.288 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4353 reflections
a = 25.102 (7) Å	θ = 2.7–29.1°
b = 12.013 (3) Å	µ = 0.10 mm−1
c = 10.436 (3) Å	T = 153 K
β = 96.248 (4)°	Platelet, colorless
V = 3128.4 (16) Å3	0.48 × 0.44 × 0.09 mm
Z = 8

Rigaku AFC10/Saturn724+ diffractometer	4149 independent reflections
Radiation source: Rotating Anode	2994 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 2.7°
phi and ω scans	h = −34→32
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −16→16
Tmin = 0.956, Tmax = 0.992	l = −13→14
16240 measured reflections

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) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0616P)2 + 0.136P] where P = (Fo2 + 2Fc2)/3
4149 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.17 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
O1	0.15659 (4)	0.22114 (7)	0.47309 (9)	0.0364 (2)
O2	0.32432 (3)	0.36646 (7)	0.09862 (8)	0.0255 (2)
O3	0.27763 (4)	0.46231 (7)	0.23556 (8)	0.0306 (2)
O4	0.42663 (4)	0.39232 (8)	−0.00208 (9)	0.0364 (2)
N1	0.16467 (4)	0.40528 (8)	0.53128 (10)	0.0250 (2)
N2	0.21226 (4)	0.33631 (8)	0.37397 (9)	0.0240 (2)
N3	0.28465 (4)	0.09868 (8)	0.07213 (10)	0.0289 (3)
C1	0.11615 (5)	0.52205 (11)	0.66349 (12)	0.0307 (3)
H1	0.1298	0.5844	0.6216	0.037*
C2	0.08347 (6)	0.53787 (13)	0.76109 (13)	0.0375 (3)
H2	0.0747	0.6112	0.7858	0.045*
C3	0.06367 (6)	0.44733 (14)	0.82240 (13)	0.0396 (3)
H3	0.0416	0.4583	0.8896	0.047*
C4	0.07616 (5)	0.34066 (13)	0.78556 (13)	0.0362 (3)
H4	0.0625	0.2785	0.8278	0.043*
C5	0.10845 (5)	0.32346 (11)	0.68761 (12)	0.0282 (3)
H5	0.1165	0.2500	0.6622	0.034*
C6	0.12894 (5)	0.41423 (10)	0.62707 (11)	0.0232 (3)
C7	0.17519 (5)	0.31405 (9)	0.46344 (12)	0.0242 (3)
C8	0.22843 (5)	0.25503 (9)	0.29863 (11)	0.0227 (3)
H8	0.2142	0.1827	0.3086	0.027*
C9	0.26364 (5)	0.26801 (9)	0.20886 (11)	0.0221 (2)
C10	0.28862 (5)	0.37541 (10)	0.18432 (11)	0.0229 (3)
C11	0.34591 (5)	0.47118 (10)	0.05780 (13)	0.0291 (3)
H11A	0.3684	0.5062	0.1306	0.035*
H11B	0.3164	0.5229	0.0284	0.035*
C12	0.37881 (5)	0.44736 (11)	−0.05006 (12)	0.0306 (3)
H12A	0.3581	0.4000	−0.1153	0.037*
H12B	0.3876	0.5179	−0.0921	0.037*
C13	0.45942 (7)	0.36769 (16)	−0.10075 (16)	0.0567 (5)
H13A	0.4701	0.4375	−0.1414	0.068*
H13B	0.4393	0.3214	−0.1680	0.068*
C14	0.50822 (8)	0.30642 (17)	−0.0432 (2)	0.0745 (6)
H14A	0.5255	0.3486	0.0303	0.112*
H14B	0.5333	0.2978	−0.1082	0.112*
H14C	0.4978	0.2328	−0.0140	0.112*
C15	0.27583 (5)	0.17378 (9)	0.13389 (11)	0.0225 (2)
H2N	0.2248 (6)	0.4059 (13)	0.3597 (14)	0.038 (4)*
H1N	0.1787 (6)	0.4663 (13)	0.5061 (13)	0.035 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0471 (6)	0.0169 (4)	0.0493 (6)	−0.0065 (4)	0.0241 (5)	−0.0041 (4)
O2	0.0295 (5)	0.0150 (4)	0.0342 (5)	0.0004 (3)	0.0134 (4)	0.0003 (3)
O3	0.0400 (5)	0.0168 (4)	0.0375 (5)	−0.0024 (4)	0.0153 (4)	−0.0060 (4)
O4	0.0314 (5)	0.0425 (6)	0.0375 (5)	0.0078 (4)	0.0141 (4)	0.0064 (4)
N1	0.0334 (6)	0.0155 (5)	0.0278 (5)	−0.0017 (4)	0.0116 (5)	0.0003 (4)
N2	0.0296 (6)	0.0155 (5)	0.0285 (5)	−0.0011 (4)	0.0100 (4)	−0.0003 (4)
N3	0.0372 (6)	0.0178 (5)	0.0324 (6)	0.0009 (4)	0.0075 (5)	−0.0013 (4)
C1	0.0371 (7)	0.0251 (6)	0.0304 (7)	0.0022 (5)	0.0059 (6)	−0.0027 (5)
C2	0.0379 (8)	0.0414 (8)	0.0337 (7)	0.0084 (6)	0.0059 (6)	−0.0101 (6)
C3	0.0309 (7)	0.0592 (10)	0.0302 (7)	0.0019 (7)	0.0106 (6)	−0.0055 (7)
C4	0.0303 (7)	0.0464 (9)	0.0330 (7)	−0.0043 (6)	0.0084 (6)	0.0058 (6)
C5	0.0283 (7)	0.0285 (6)	0.0283 (6)	−0.0019 (5)	0.0057 (5)	0.0028 (5)
C6	0.0235 (6)	0.0252 (6)	0.0212 (6)	0.0009 (4)	0.0031 (5)	−0.0007 (5)
C7	0.0271 (6)	0.0182 (6)	0.0282 (6)	0.0003 (4)	0.0070 (5)	0.0011 (5)
C8	0.0265 (6)	0.0161 (5)	0.0256 (6)	0.0003 (4)	0.0030 (5)	−0.0002 (4)
C9	0.0259 (6)	0.0146 (5)	0.0261 (6)	0.0014 (4)	0.0045 (5)	−0.0008 (4)
C10	0.0254 (6)	0.0181 (6)	0.0258 (6)	0.0011 (4)	0.0049 (5)	−0.0009 (4)
C11	0.0336 (7)	0.0165 (6)	0.0391 (7)	−0.0024 (5)	0.0123 (6)	0.0018 (5)
C12	0.0333 (7)	0.0263 (6)	0.0337 (7)	0.0011 (5)	0.0101 (6)	0.0050 (5)
C13	0.0563 (10)	0.0660 (12)	0.0536 (10)	0.0232 (9)	0.0333 (8)	0.0157 (8)
C14	0.0570 (12)	0.0897 (16)	0.0838 (14)	0.0342 (11)	0.0399 (11)	0.0275 (12)
C15	0.0255 (6)	0.0172 (5)	0.0251 (6)	0.0001 (4)	0.0046 (5)	0.0030 (4)

O1—C7	1.2183 (14)	C4—C5	1.3875 (18)
O2—C10	1.3376 (14)	C4—H4	0.9500
O2—C11	1.4520 (14)	C5—C6	1.3869 (17)
O3—C10	1.2181 (14)	C5—H5	0.9500
O4—C12	1.4135 (15)	C8—C9	1.3650 (16)
O4—C13	1.4177 (17)	C8—H8	0.9500
N1—C7	1.3465 (15)	C9—C15	1.4281 (16)
N1—C6	1.4179 (15)	C9—C10	1.4691 (16)
N1—H1N	0.867 (15)	C11—C12	1.4943 (18)
N2—C8	1.3439 (15)	C11—H11A	0.9900
N2—C7	1.4136 (15)	C11—H11B	0.9900
N2—H2N	0.910 (15)	C12—H12A	0.9900
N3—C15	1.1443 (15)	C12—H12B	0.9900
C1—C2	1.3887 (18)	C13—C14	1.498 (2)
C1—C6	1.3970 (17)	C13—H13A	0.9900
C1—H1	0.9500	C13—H13B	0.9900
C2—C3	1.382 (2)	C14—H14A	0.9800
C2—H2	0.9500	C14—H14B	0.9800
C3—C4	1.384 (2)	C14—H14C	0.9800
C3—H3	0.9500
C10—O2—C11	115.17 (9)	C8—C9—C15	118.61 (11)
C12—O4—C13	112.22 (11)	C8—C9—C10	122.71 (10)
C7—N1—C6	127.43 (10)	C15—C9—C10	118.66 (10)
C7—N1—H1N	114.8 (10)	O3—C10—O2	124.24 (11)
C6—N1—H1N	117.3 (10)	O3—C10—C9	123.70 (11)
C8—N2—C7	120.76 (10)	O2—C10—C9	112.06 (10)
C8—N2—H2N	116.1 (9)	O2—C11—C12	108.04 (10)
C7—N2—H2N	123.0 (9)	O2—C11—H11A	110.1
C2—C1—C6	119.87 (13)	C12—C11—H11A	110.1
C2—C1—H1	120.1	O2—C11—H11B	110.1
C6—C1—H1	120.1	C12—C11—H11B	110.1
C3—C2—C1	120.20 (13)	H11A—C11—H11B	108.4
C3—C2—H2	119.9	O4—C12—C11	109.89 (10)
C1—C2—H2	119.9	O4—C12—H12A	109.7
C2—C3—C4	119.78 (13)	C11—C12—H12A	109.7
C2—C3—H3	120.1	O4—C12—H12B	109.7
C4—C3—H3	120.1	C11—C12—H12B	109.7
C3—C4—C5	120.72 (13)	H12A—C12—H12B	108.2
C3—C4—H4	119.6	O4—C13—C14	108.98 (14)
C5—C4—H4	119.6	O4—C13—H13A	109.9
C6—C5—C4	119.60 (13)	C14—C13—H13A	109.9
C6—C5—H5	120.2	O4—C13—H13B	109.9
C4—C5—H5	120.2	C14—C13—H13B	109.9
C5—C6—C1	119.82 (12)	H13A—C13—H13B	108.3
C5—C6—N1	123.78 (11)	C13—C14—H14A	109.5
C1—C6—N1	116.35 (11)	C13—C14—H14B	109.5
O1—C7—N1	127.11 (12)	H14A—C14—H14B	109.5
O1—C7—N2	120.92 (11)	C13—C14—H14C	109.5
N1—C7—N2	111.98 (10)	H14A—C14—H14C	109.5
N2—C8—C9	125.30 (11)	H14B—C14—H14C	109.5
N2—C8—H8	117.3	N3—C15—C9	178.57 (13)
C9—C8—H8	117.3
C6—C1—C2—C3	0.1 (2)	C7—N2—C8—C9	179.49 (11)
C1—C2—C3—C4	−0.5 (2)	N2—C8—C9—C15	−178.46 (11)
C2—C3—C4—C5	0.1 (2)	N2—C8—C9—C10	0.22 (19)
C3—C4—C5—C6	0.8 (2)	C11—O2—C10—O3	−6.56 (17)
C4—C5—C6—C1	−1.16 (18)	C11—O2—C10—C9	172.90 (10)
C4—C5—C6—N1	176.29 (11)	C8—C9—C10—O3	−4.72 (19)
C2—C1—C6—C5	0.71 (19)	C15—C9—C10—O3	173.95 (11)
C2—C1—C6—N1	−176.93 (11)	C8—C9—C10—O2	175.81 (10)
C7—N1—C6—C5	15.9 (2)	C15—C9—C10—O2	−5.52 (16)
C7—N1—C6—C1	−166.53 (12)	C10—O2—C11—C12	−172.26 (10)
C6—N1—C7—O1	−1.3 (2)	C13—O4—C12—C11	180.00 (13)
C6—N1—C7—N2	178.81 (11)	O2—C11—C12—O4	−71.42 (13)
C8—N2—C7—O1	−0.93 (18)	C12—O4—C13—C14	−178.18 (14)
C8—N2—C7—N1	178.97 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O3	0.910 (15)	2.068 (15)	2.7543 (14)	131.2 (12)
N1—H1N···N3i	0.867 (15)	2.050 (15)	2.9120 (15)	172.6 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3	0.910 (15)	2.068 (15)	2.7543 (14)	131.2 (12)
N1—H1N⋯N3i	0.867 (15)	2.050 (15)	2.9120 (15)	172.6 (14)

Symmetry code: (i) .