Dimethyl (E)-2-(N-phenyl-acetamido)-but-2-enedioate.

The title compound, C(14)H(15)NO(5), was obtained from the reaction of acetanilide with dimethyl acetyl-enedicarboxyl-ate in the presence of potassium carbonate. The C=C double bond adopts an E configuration and the geometry around the amide N atom is almost planar rather than pyramidal (mean deviation of 0.0032 Å from the C(3)N plane). The packing of the mol-ecules in the crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background to the hydro­amidation of alkynes, see: Severin & Doye (2007) ▶; Goossen et al. (2005 ▶); Cacchi & Fabrizi (2005) ▶; For structurally related compounds, see: Kawahara et al. (1989 ▶); Penney et al. (1995 ▶); Yet et al. (2003 ▶); Hua et al. (2003 ▶).

Experimental

Crystal data

C14H15NO5

M = 277.27

Monoclinic,

a = 9.7920 (5) Å

b = 12.1917 (4) Å

c = 12.2281 (6) Å

β = 112.629 (6)°

V = 1347.42 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.15 × 0.12 × 0.10 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.885, T max = 1.000

7263 measured reflections

3009 independent reflections

2415 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.00

3009 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050890/zl2334sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050890/zl2334Isup2.hkl

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

C14H15NO5	F(000) = 584
Mr = 277.27	Dx = 1.367 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4186 reflections
a = 9.7920 (5) Å	θ = 2.8–29.0°
b = 12.1917 (4) Å	µ = 0.11 mm−1
c = 12.2281 (6) Å	T = 173 K
β = 112.629 (6)°	Block, colorless
V = 1347.42 (11) Å3	0.15 × 0.12 × 0.10 mm
Z = 4

Oxford Diffraction Gemini S Ultra diffractometer	3009 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2415 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 16.1930 pixels mm-1	θmax = 27.5°, θmin = 2.8°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −15→10
Tmin = 0.885, Tmax = 1.000	l = −14→15
7263 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3
3009 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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 > 2sigma(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	0.35048 (9)	0.34762 (7)	0.14129 (7)	0.0233 (2)
N1	0.65965 (10)	0.10602 (8)	0.11896 (8)	0.0173 (2)
C1	0.50153 (12)	0.26233 (10)	0.05139 (10)	0.0184 (2)
H1A	0.5426	0.2750	−0.0045	0.022*
O2	0.36589 (9)	0.41845 (7)	−0.02353 (7)	0.0233 (2)
C2	0.54018 (12)	0.17090 (9)	0.11658 (10)	0.0166 (2)
O3	0.53999 (10)	0.14493 (7)	0.30872 (7)	0.0265 (2)
C3	0.39784 (12)	0.34379 (9)	0.06335 (10)	0.0184 (2)
O4	0.33137 (9)	0.10799 (7)	0.15035 (7)	0.0211 (2)
C4	0.27339 (14)	0.50801 (10)	−0.01660 (12)	0.0268 (3)
H4A	0.2562	0.5569	−0.0821	0.040*
H4B	0.3218	0.5470	0.0563	0.040*
H4C	0.1806	0.4797	−0.0194	0.040*
O5	0.56257 (9)	−0.04796 (7)	0.16290 (8)	0.0233 (2)
C5	0.47167 (13)	0.13911 (9)	0.20343 (10)	0.0185 (3)
C6	0.26254 (15)	0.07359 (11)	0.22997 (12)	0.0295 (3)
H6A	0.1618	0.0529	0.1850	0.044*
H6B	0.2646	0.1330	0.2821	0.044*
H6C	0.3154	0.0120	0.2757	0.044*
C7	0.66568 (12)	−0.00447 (9)	0.14735 (10)	0.0179 (2)
C8	0.80390 (13)	−0.06526 (11)	0.15872 (11)	0.0251 (3)
H8A	0.7954	−0.1405	0.1783	0.038*
H8B	0.8875	−0.0324	0.2201	0.038*
H8C	0.8171	−0.0617	0.0850	0.038*
C11	0.77404 (12)	0.15731 (9)	0.08915 (10)	0.0167 (2)
C12	0.77754 (13)	0.14120 (10)	−0.02186 (10)	0.0195 (3)
H12A	0.7062	0.0980	−0.0778	0.023*
C13	0.88875 (13)	0.19028 (10)	−0.04866 (11)	0.0224 (3)
H13A	0.8931	0.1790	−0.1225	0.027*
C14	0.99298 (13)	0.25583 (10)	0.03413 (11)	0.0247 (3)
H14A	1.0673	0.2887	0.0159	0.030*
C15	0.98695 (13)	0.27261 (10)	0.14413 (11)	0.0240 (3)
H15A	1.0568	0.3173	0.1993	0.029*
C16	0.87727 (13)	0.22307 (10)	0.17251 (11)	0.0208 (3)
H16A	0.8733	0.2339	0.2465	0.025*

	U11	U22	U33	U12	U13	U23
O1	0.0234 (5)	0.0234 (5)	0.0264 (5)	0.0029 (4)	0.0133 (4)	−0.0002 (4)
N1	0.0167 (5)	0.0172 (5)	0.0206 (5)	0.0008 (4)	0.0101 (4)	0.0014 (4)
C1	0.0176 (5)	0.0211 (6)	0.0188 (6)	−0.0008 (5)	0.0094 (5)	−0.0001 (5)
O2	0.0258 (5)	0.0194 (4)	0.0259 (5)	0.0052 (4)	0.0112 (4)	0.0038 (4)
C2	0.0147 (5)	0.0190 (6)	0.0166 (6)	−0.0013 (4)	0.0065 (4)	−0.0031 (4)
O3	0.0285 (5)	0.0340 (5)	0.0187 (4)	0.0051 (4)	0.0111 (4)	−0.0002 (4)
C3	0.0147 (5)	0.0179 (6)	0.0209 (6)	−0.0038 (4)	0.0049 (5)	−0.0015 (5)
O4	0.0193 (4)	0.0218 (4)	0.0269 (5)	−0.0009 (3)	0.0140 (4)	0.0020 (3)
C4	0.0282 (7)	0.0187 (6)	0.0326 (7)	0.0055 (5)	0.0106 (5)	0.0020 (5)
O5	0.0236 (4)	0.0204 (4)	0.0297 (5)	−0.0009 (4)	0.0145 (4)	0.0033 (4)
C5	0.0195 (6)	0.0160 (6)	0.0228 (6)	0.0032 (4)	0.0113 (5)	0.0002 (5)
C6	0.0331 (7)	0.0262 (7)	0.0417 (8)	0.0001 (6)	0.0284 (6)	0.0036 (6)
C7	0.0207 (6)	0.0190 (6)	0.0147 (5)	0.0009 (5)	0.0077 (4)	0.0009 (4)
C8	0.0245 (6)	0.0220 (6)	0.0308 (7)	0.0055 (5)	0.0130 (5)	0.0076 (5)
C11	0.0161 (6)	0.0156 (5)	0.0207 (6)	0.0033 (4)	0.0097 (5)	0.0032 (5)
C12	0.0185 (6)	0.0200 (6)	0.0204 (6)	−0.0011 (5)	0.0079 (5)	−0.0011 (5)
C13	0.0234 (6)	0.0258 (6)	0.0222 (6)	0.0001 (5)	0.0134 (5)	0.0024 (5)
C14	0.0194 (6)	0.0241 (6)	0.0336 (7)	−0.0012 (5)	0.0135 (5)	0.0070 (5)
C15	0.0187 (6)	0.0211 (6)	0.0292 (7)	−0.0029 (5)	0.0059 (5)	−0.0017 (5)
C16	0.0204 (6)	0.0212 (6)	0.0207 (6)	0.0021 (5)	0.0078 (5)	−0.0006 (5)

O1—C3	1.2106 (14)	C6—H6B	0.9600
N1—C7	1.3867 (15)	C6—H6C	0.9600
N1—C2	1.4031 (14)	C7—C8	1.5019 (16)
N1—C11	1.4466 (14)	C8—H8A	0.9600
C1—C2	1.3376 (16)	C8—H8B	0.9600
C1—C3	1.4672 (16)	C8—H8C	0.9600
C1—H1A	0.9300	C11—C16	1.3823 (16)
O2—C3	1.3413 (14)	C11—C12	1.3849 (16)
O2—C4	1.4418 (14)	C12—C13	1.3878 (15)
C2—C5	1.5088 (15)	C12—H12A	0.9300
O3—C5	1.2030 (14)	C13—C14	1.3820 (18)
O4—C5	1.3290 (14)	C13—H13A	0.9300
O4—C6	1.4432 (13)	C14—C15	1.3841 (18)
C4—H4A	0.9600	C14—H14A	0.9300
C4—H4B	0.9600	C15—C16	1.3876 (16)
C4—H4C	0.9600	C15—H15A	0.9300
O5—C7	1.2183 (14)	C16—H16A	0.9300
C6—H6A	0.9600
C7—N1—C2	120.51 (9)	H6B—C6—H6C	109.5
C7—N1—C11	121.36 (9)	O5—C7—N1	120.25 (10)
C2—N1—C11	118.12 (9)	O5—C7—C8	122.84 (11)
C2—C1—C3	123.55 (10)	N1—C7—C8	116.91 (10)
C2—C1—H1A	118.2	C7—C8—H8A	109.5
C3—C1—H1A	118.2	C7—C8—H8B	109.5
C3—O2—C4	115.32 (9)	H8A—C8—H8B	109.5
C1—C2—N1	121.65 (10)	C7—C8—H8C	109.5
C1—C2—C5	122.21 (10)	H8A—C8—H8C	109.5
N1—C2—C5	115.69 (9)	H8B—C8—H8C	109.5
O1—C3—O2	123.64 (10)	C16—C11—C12	121.21 (10)
O1—C3—C1	126.44 (11)	C16—C11—N1	118.84 (10)
O2—C3—C1	109.87 (10)	C12—C11—N1	119.95 (10)
C5—O4—C6	114.63 (10)	C11—C12—C13	119.20 (11)
O2—C4—H4A	109.5	C11—C12—H12A	120.4
O2—C4—H4B	109.5	C13—C12—H12A	120.4
H4A—C4—H4B	109.5	C14—C13—C12	120.11 (11)
O2—C4—H4C	109.5	C14—C13—H13A	119.9
H4A—C4—H4C	109.5	C12—C13—H13A	119.9
H4B—C4—H4C	109.5	C13—C14—C15	120.12 (11)
O3—C5—O4	125.75 (11)	C13—C14—H14A	119.9
O3—C5—C2	121.56 (11)	C15—C14—H14A	119.9
O4—C5—C2	112.68 (10)	C14—C15—C16	120.35 (11)
O4—C6—H6A	109.5	C14—C15—H15A	119.8
O4—C6—H6B	109.5	C16—C15—H15A	119.8
H6A—C6—H6B	109.5	C11—C16—C15	119.00 (11)
O4—C6—H6C	109.5	C11—C16—H16A	120.5
H6A—C6—H6C	109.5	C15—C16—H16A	120.5

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4C···O3i	0.96	2.53	3.0831 (16)	117.
C14—H14A···O3ii	0.93	2.57	3.2016 (15)	125.
C12—H12A···O5iii	0.93	2.51	3.3073 (15)	145.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4C⋯O3i	0.96	2.53	3.0831 (16)	117
C14—H14A⋯O3ii	0.93	2.57	3.2016 (15)	125
C12—H12A⋯O5iii	0.93	2.51	3.3073 (15)	145

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