(Z)-2-Acetamido-3-(4-chloro-phen-yl)acrylic acid.

In the title compound, C(11)H(10)ClNO(3), the mol-ecule consists of a benzene ring and an acetamido-acrylic acid unit on opposite sides of the C=C double bond. In the crystal, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds assemble the mol-ecules into infinite two-dimensional ribbons. These ribbons are linked into a network by inter-molecular C-H⋯π contacts.

Related literature

Derivatives of 2-acetamido-3-phenyl­acrylic acid are key inter­mates in the preparations of tanshinol (Wong et al. 1992 ▶; Xiao, et al. 2008a ▶), diaryl-3-hydr­oxy-2(5H)-furan­ones (Weber et al. 2002 ▶; Xiao et al. 2008b ▶) and benzyl­azauracil (Chen et al. 1993 ▶; Xiao, et al. 2008c ▶), which show anti-platelet aggregation, anti­fungal and anti­viral activities, respectively.

Experimental

Crystal data

C11H10ClNO3

M = 239.65

Monoclinic,

a = 6.2440 (12) Å

b = 7.5450 (15) Å

c = 11.813 (2) Å

β = 100.47 (3)°

V = 547.26 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 298 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.935, T max = 0.967

1160 measured reflections

1060 independent reflections

895 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.229

S = 1.01

1060 reflections

148 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S1600536809048041/bq2173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048041/bq2173Isup2.hkl

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

C11H10ClNO3	F(000) = 248
Mr = 239.65	Dx = 1.454 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 775 reflections
a = 6.2440 (12) Å	θ = 1.9–24.7°
b = 7.5450 (15) Å	µ = 0.34 mm−1
c = 11.813 (2) Å	T = 298 K
β = 100.47 (3)°	Block, colorless
V = 547.26 (19) Å3	0.20 × 0.10 × 0.10 mm
Z = 2

Bruker SMART APEX area-detector diffractometer	1060 independent reflections
Radiation source: fine-focus sealed tube	895 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 25.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 0→7
Tmin = 0.935, Tmax = 0.967	k = 0→9
1160 measured reflections	l = −14→13

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.229	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
1060 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.35 e Å−3

Experimental. We have re-refined our data by using 'MERG 1' instruction to avoid Friedel opposites being merged. The absolute structure parameter is still meaningless, though the data/parameter (985/148) is higher than the former (895/148).

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
Cl	−0.0425 (4)	0.7267 (4)	0.74675 (17)	0.0628 (8)
C1	0.3337 (10)	0.6719 (8)	0.4546 (5)	0.0297 (14)
N1	0.2032 (8)	0.7163 (9)	0.1907 (4)	0.0333 (13)
H1	0.0860	0.6715	0.2071	0.06 (3)*
O1	0.7621 (7)	0.6067 (9)	0.2131 (5)	0.0529 (16)
C2	0.1323 (11)	0.7587 (9)	0.4407 (6)	0.0360 (16)
H2	0.0726	0.8045	0.3688	0.043*
O2	0.4735 (8)	0.5437 (10)	0.0782 (5)	0.0579 (17)
H2A	0.5657	0.5193	0.0393	0.087*
C3	0.0201 (13)	0.7786 (10)	0.5294 (6)	0.0422 (18)
H3	−0.1134	0.8368	0.5177	0.051*
O3	0.3510 (8)	0.9179 (9)	0.0890 (4)	0.0496 (15)
C4	0.1089 (13)	0.7102 (11)	0.6378 (6)	0.0436 (18)
C5	0.3095 (13)	0.6317 (12)	0.6558 (6)	0.0480 (19)
H5	0.3701	0.5915	0.7291	0.058*
C6	0.4220 (11)	0.6116 (11)	0.5683 (6)	0.0424 (18)
H6	0.5582	0.5577	0.5825	0.051*
C7	0.4613 (10)	0.6378 (10)	0.3662 (6)	0.0337 (14)
H7	0.6012	0.5950	0.3924	0.040*
C8	0.4067 (10)	0.6591 (10)	0.2525 (6)	0.0352 (15)
C9	0.5701 (10)	0.6022 (10)	0.1796 (6)	0.0372 (16)
C10	0.1874 (11)	0.8392 (10)	0.1065 (5)	0.0363 (15)
C11	−0.0380 (12)	0.8731 (13)	0.0403 (6)	0.050 (2)
H11A	−0.0295	0.9462	−0.0252	0.075*
H11B	−0.1227	0.9323	0.0891	0.075*
H11C	−0.1059	0.7624	0.0149	0.075*

	U11	U22	U33	U12	U13	U23
Cl	0.0756 (15)	0.0751 (15)	0.0438 (10)	−0.0037 (13)	0.0266 (10)	−0.0043 (11)
C1	0.028 (3)	0.032 (3)	0.026 (3)	−0.003 (3)	−0.001 (2)	0.002 (2)
N1	0.027 (3)	0.045 (3)	0.032 (2)	0.000 (3)	0.016 (2)	0.004 (3)
O1	0.025 (2)	0.077 (4)	0.057 (3)	0.003 (3)	0.005 (2)	0.000 (3)
C2	0.041 (4)	0.033 (4)	0.034 (3)	0.008 (3)	0.006 (3)	0.004 (3)
O2	0.033 (2)	0.084 (4)	0.058 (3)	−0.001 (3)	0.012 (2)	−0.034 (4)
C3	0.037 (4)	0.046 (4)	0.045 (4)	0.004 (3)	0.011 (3)	0.000 (3)
O3	0.047 (3)	0.063 (4)	0.041 (3)	−0.013 (3)	0.015 (2)	0.014 (3)
C4	0.051 (4)	0.038 (4)	0.040 (4)	−0.008 (4)	0.003 (3)	−0.002 (3)
C5	0.059 (5)	0.054 (5)	0.030 (3)	−0.005 (4)	0.005 (3)	0.006 (3)
C6	0.038 (4)	0.046 (4)	0.039 (4)	0.012 (3)	−0.004 (3)	0.008 (3)
C7	0.027 (3)	0.035 (3)	0.040 (3)	0.002 (3)	0.006 (2)	0.002 (3)
C8	0.029 (3)	0.034 (3)	0.045 (4)	0.000 (3)	0.014 (3)	0.003 (3)
C9	0.033 (3)	0.044 (4)	0.041 (4)	−0.004 (3)	0.022 (3)	−0.002 (3)
C10	0.040 (3)	0.044 (4)	0.029 (3)	0.005 (3)	0.016 (3)	−0.003 (3)
C11	0.054 (4)	0.057 (5)	0.034 (3)	0.011 (4)	−0.006 (3)	0.006 (4)

Cl—C4	1.734 (8)	C3—H3	0.9300
C1—C2	1.401 (9)	O3—C10	1.231 (9)
C1—C6	1.430 (9)	C4—C5	1.367 (12)
C1—C7	1.446 (9)	C5—C6	1.360 (11)
N1—C10	1.350 (9)	C5—H5	0.9300
N1—C8	1.413 (9)	C6—H6	0.9300
N1—H1	0.8600	C7—C8	1.334 (11)
O1—C9	1.193 (8)	C7—H7	0.9300
C2—C3	1.370 (11)	C8—C9	1.512 (8)
C2—H2	0.9300	C10—C11	1.502 (10)
O2—C9	1.316 (9)	C11—H11A	0.9600
O2—H2A	0.8200	C11—H11B	0.9600
C3—C4	1.398 (11)	C11—H11C	0.9600
C2—C1—C6	116.3 (6)	C5—C6—H6	119.5
C2—C1—C7	126.8 (6)	C1—C6—H6	119.5
C6—C1—C7	116.9 (6)	C8—C7—C1	129.2 (6)
C10—N1—C8	121.9 (6)	C8—C7—H7	115.4
C10—N1—H1	119.0	C1—C7—H7	115.4
C8—N1—H1	119.0	C7—C8—N1	126.8 (6)
C3—C2—C1	122.3 (6)	C7—C8—C9	117.6 (6)
C3—C2—H2	118.8	N1—C8—C9	115.4 (6)
C1—C2—H2	118.8	O1—C9—O2	125.3 (6)
C9—O2—H2A	109.5	O1—C9—C8	123.0 (6)
C4—C3—C2	119.2 (7)	O2—C9—C8	111.7 (5)
C4—C3—H3	120.4	O3—C10—N1	120.2 (6)
C2—C3—H3	120.4	O3—C10—C11	123.9 (7)
C3—C4—C5	120.1 (7)	N1—C10—C11	115.9 (6)
C3—C4—Cl	118.3 (6)	C10—C11—H11A	109.5
C5—C4—Cl	121.6 (6)	C10—C11—H11B	109.5
C4—C5—C6	121.0 (7)	H11A—C11—H11B	109.5
C4—C5—H5	119.5	C10—C11—H11C	109.5
C6—C5—H5	119.5	H11A—C11—H11C	109.5
C5—C6—C1	121.0 (6)	H11B—C11—H11C	109.5
C6—C1—C2—C3	−2.8 (10)	C6—C1—C7—C8	170.8 (8)
C7—C1—C2—C3	177.5 (7)	C1—C7—C8—N1	−2.2 (13)
C1—C2—C3—C4	0.0 (11)	C1—C7—C8—C9	−176.5 (7)
C2—C3—C4—C5	2.9 (12)	C10—N1—C8—C7	134.8 (8)
C2—C3—C4—Cl	−176.7 (6)	C10—N1—C8—C9	−50.8 (9)
C3—C4—C5—C6	−2.9 (13)	C7—C8—C9—O1	−30.5 (11)
Cl—C4—C5—C6	176.6 (6)	N1—C8—C9—O1	154.6 (8)
C4—C5—C6—C1	0.0 (12)	C7—C8—C9—O2	147.7 (8)
C2—C1—C6—C5	2.8 (11)	N1—C8—C9—O2	−27.2 (10)
C7—C1—C6—C5	−177.5 (7)	C8—N1—C10—O3	−7.2 (11)
C2—C1—C7—C8	−9.5 (12)	C8—N1—C10—C11	174.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.09	2.933 (7)	165
O2—H2A···O3ii	0.82	1.86	2.606 (7)	152
C3—H3···Cg1iii	0.93	2.85	3.523 (8)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.09	2.933 (7)	165
O2—H2A⋯O3ii	0.82	1.86	2.606 (7)	152
C3—H3⋯Cg1iii	0.93	2.85	3.523 (8)	130

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring.