(E)-2-Cyano-3-(2,3-dimeth-oxy-phen-yl)acrylic acid.

The asymmetric unit of the title compound, C(12)H(11)NO(4), contains two mol-ecules. In the crystal, neighbouring mol-ecules are linked together by O-H⋯O hydrogen bonds into dimers. The dimers are arranged into columns parallel to the a axis, meditated by π-π inter-actions [centroid-centroid distances = 3.856 (3) and 3.857 (3) Å]. The crystal structure is further stabilized by weak inter-molecular C-H⋯O inter-actions. The crystal studied was a non-merohedral twin with a ratio of the twin components of 0.657 (11):0.343 (11).

Related literature

For applications of cyano­acrylic acid derivatives, see: Hagberg et al. (2006 ▶); Kim et al. (2008 ▶); Hara et al. (2003 ▶). For structures and properties of complexes based on carboxyl­ate ligands, see, for example: Zhao et al. (2008 ▶); Wang et al. (2009 ▶); Mitra et al. (2006 ▶); Shit et al. (2009 ▶); Akhbari et al. (2009 ▶).

Experimental

Crystal data

C12H11NO4

M = 233.2

Monoclinic,

a = 3.8564 (5) Å

b = 27.178 (3) Å

c = 10.4681 (9) Å

β = 99.966 (9)°

V = 1080.6 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.92 mm−1

T = 120 K

0.57 × 0.15 × 0.05 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.525, T max = 1

17777 measured reflections

1922 independent reflections

1638 reflections with I > 3σ(I)

R int = 0.083

Refinement

R[F 2 > 3σ(F 2)] = 0.049

wR(F 2) = 0.129

S = 1.73

1922 reflections

314 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶) and COOT (Emsley et al., 2010 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051129/bt5719sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051129/bt5719Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051129/bt5719Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811051129/bt5719Isup4.cml

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

C12H11NO4	F(000) = 488
Mr = 233.2	Dx = 1.433 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2yb	Cell parameters from 10329 reflections
a = 3.8564 (5) Å	θ = 3.2–67.0°
b = 27.178 (3) Å	µ = 0.92 mm−1
c = 10.4681 (9) Å	T = 120 K
β = 99.966 (9)°	Plate, yellow
V = 1080.6 (2) Å3	0.57 × 0.15 × 0.05 mm
Z = 4

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1922 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1638 reflections with I > 3σ(I)
mirror	Rint = 0.083
Detector resolution: 10.3784 pixels mm-1	θmax = 67.2°, θmin = 3.3°
Rotation method data acquisition using ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −32→32
Tmin = 0.525, Tmax = 1	l = −12→12
17777 measured reflections

Refinement on F2	83 constraints
R[F2 > 2σ(F2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0025000002I2]
S = 1.73	(Δ/σ)max = 0.005
1922 reflections	Δρmax = 0.23 e Å−3
314 parameters	Δρmin = −0.23 e Å−3
2 restraints

Experimental. CrysAlisPro (Agilent Technologies, 2010) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.The crystal studied was a non-merohedral twin with a minor twin domain of 24.7 (8)%. The overlaps of reflection between the twin domains were calculated by Jana2006 software using the twinning matrix and user- defined thresholds 0.23° for full overlap and 0.35° for full separation. For fully overlapped reflections, only a partial F2, corresponding to the twin volume fraction, were used in the refinement. Partially overlapped reflections were discarded from the refinement.

	x	y	z	Uiso*/Ueq
O1	0.2649 (11)	0.6335 (11)	0.4130 (3)	0.0326 (11)
O2	0.4957 (11)	0.5846 (11)	0.2764 (3)	0.0345 (12)
O3	−0.0165 (9)	0.5839 (11)	0.7938 (3)	0.0283 (10)
O4	−0.1254 (10)	0.5233 (11)	0.9851 (3)	0.0308 (11)
O5	0.5833 (10)	0.6646 (11)	1.1452 (3)	0.0320 (12)
O6	0.3472 (10)	0.7133 (11)	1.2816 (3)	0.0332 (12)
O7	0.8594 (9)	0.7170 (11)	0.7627 (3)	0.0283 (10)
O8	0.9534 (10)	0.7793 (11)	0.5719 (3)	0.0342 (12)
N1	0.5464 (13)	0.4678 (11)	0.3684 (4)	0.0343 (14)
N2	0.2837 (13)	0.8295 (11)	1.1899 (4)	0.0321 (14)
C1	0.1528 (12)	0.5171 (11)	0.6702 (5)	0.0236 (14)
C2	0.0453 (13)	0.5351 (11)	0.7835 (4)	0.0236 (14)
C3	−0.0160 (12)	0.5019 (11)	0.8808 (4)	0.0245 (14)
C4	0.0298 (13)	0.4524 (11)	0.8650 (4)	0.0255 (14)
C5	0.1332 (14)	0.4346 (11)	0.7525 (5)	0.0288 (15)
C6	0.1917 (13)	0.4663 (11)	0.6560 (4)	0.0274 (15)
C7	0.2100 (13)	0.5534 (11)	0.5742 (4)	0.0250 (14)
C8	0.3328 (14)	0.5483 (11)	0.4605 (4)	0.0243 (14)
C9	0.4445 (14)	0.5034 (11)	0.4110 (4)	0.0277 (14)
C10	0.3636 (13)	0.5926 (11)	0.3818 (4)	0.0257 (14)
C11	0.1964 (15)	0.6094 (11)	0.9025 (5)	0.0332 (16)
C12	−0.1818 (14)	0.4919 (11)	1.0900 (5)	0.0334 (16)
C13	0.6801 (13)	0.7825 (11)	0.8888 (4)	0.0234 (13)
C14	0.7893 (13)	0.7657 (11)	0.7738 (4)	0.0247 (14)
C15	0.8358 (13)	0.7994 (11)	0.6769 (4)	0.0283 (15)
C16	0.7721 (14)	0.8488 (11)	0.6932 (5)	0.0289 (15)
C17	0.6679 (14)	0.8651 (11)	0.8067 (5)	0.0286 (15)
C18	0.6238 (13)	0.8332 (11)	0.9037 (4)	0.0273 (15)
C19	0.6324 (13)	0.7453 (11)	0.9840 (4)	0.0229 (14)
C20	0.5098 (13)	0.7499 (11)	1.0980 (4)	0.0250 (14)
C21	0.3867 (13)	0.7943 (11)	1.1482 (4)	0.0249 (14)
C22	0.4825 (13)	0.7055 (11)	1.1777 (4)	0.0255 (14)
C23	0.6528 (14)	0.6915 (11)	0.6539 (5)	0.0311 (15)
C24	0.9902 (15)	0.8114 (11)	0.4668 (5)	0.0357 (17)
H4	−0.00949	0.429884	0.931765	0.0306*
H5	0.164009	0.399816	0.742312	0.0346*
H6	0.259432	0.453504	0.578406	0.0329*
H7	0.151405	0.586516	0.594259	0.03*
H11a	0.27646	0.640183	0.873092	0.0498*
H11b	0.05723	0.615435	0.968529	0.0498*
H11c	0.395751	0.589449	0.937303	0.0498*
H12a	−0.277146	0.510825	1.153105	0.0501*
H12b	−0.343934	0.466212	1.057065	0.0501*
H12c	0.038147	0.47757	1.129784	0.0501*
H16	0.799855	0.871938	0.626328	0.0347*
H17	0.62584	0.899564	0.817253	0.0344*
H18	0.554605	0.845365	0.981646	0.0327*
H19	0.697052	0.712524	0.963476	0.0275*
H23a	0.668317	0.656625	0.668973	0.0466*
H23b	0.411361	0.70166	0.644608	0.0466*
H23c	0.741702	0.699178	0.576118	0.0466*
H24a	1.067113	0.792805	0.398881	0.0535*
H24b	0.767556	0.826519	0.434114	0.0535*
H24c	1.160734	0.836408	0.496816	0.0535*
H6o	0.315 (19)	0.6834 (14)	1.301 (7)	0.0498*
H2o	0.50 (2)	0.6115 (17)	0.235 (6)	0.0517*

	U11	U22	U33	U12	U13	U23
O1	0.051 (2)	0.0260 (17)	0.0237 (16)	−0.0015 (15)	0.0152 (16)	0.0005 (13)
O2	0.053 (2)	0.0316 (19)	0.0222 (16)	−0.0003 (18)	0.0166 (16)	0.0036 (14)
O3	0.039 (2)	0.0282 (17)	0.0183 (14)	0.0052 (15)	0.0074 (14)	0.0006 (13)
O4	0.042 (2)	0.0356 (18)	0.0183 (15)	0.0008 (16)	0.0162 (15)	0.0033 (13)
O5	0.048 (2)	0.0256 (18)	0.0249 (18)	0.0029 (15)	0.0118 (16)	0.0038 (13)
O6	0.047 (2)	0.0329 (19)	0.0238 (16)	0.0009 (17)	0.0181 (16)	0.0038 (14)
O7	0.037 (2)	0.0304 (18)	0.0177 (14)	0.0057 (14)	0.0058 (14)	−0.0018 (13)
O8	0.046 (2)	0.042 (2)	0.0183 (16)	0.0056 (18)	0.0151 (16)	0.0045 (14)
N1	0.046 (3)	0.036 (2)	0.0238 (19)	0.000 (2)	0.0145 (19)	−0.0008 (17)
N2	0.041 (3)	0.032 (2)	0.026 (2)	−0.0008 (19)	0.0129 (19)	−0.0004 (17)
C1	0.022 (2)	0.029 (2)	0.021 (2)	0.0003 (19)	0.0066 (18)	0.0038 (18)
C2	0.022 (2)	0.028 (2)	0.021 (2)	0.0016 (18)	0.0043 (19)	0.0002 (18)
C3	0.023 (2)	0.036 (2)	0.017 (2)	0.0012 (19)	0.0094 (18)	0.0015 (19)
C4	0.026 (2)	0.031 (2)	0.020 (2)	−0.0031 (19)	0.0053 (19)	0.0032 (17)
C5	0.035 (3)	0.029 (2)	0.023 (2)	−0.002 (2)	0.008 (2)	0.0023 (18)
C6	0.032 (3)	0.030 (2)	0.022 (2)	−0.001 (2)	0.009 (2)	−0.0003 (19)
C7	0.028 (3)	0.028 (2)	0.020 (2)	−0.0008 (19)	0.0069 (19)	0.0026 (18)
C8	0.028 (3)	0.027 (2)	0.018 (2)	−0.0036 (19)	0.0045 (19)	−0.0008 (17)
C9	0.035 (3)	0.028 (2)	0.020 (2)	−0.004 (2)	0.007 (2)	0.0008 (18)
C10	0.030 (3)	0.030 (3)	0.018 (2)	−0.0027 (19)	0.0073 (19)	0.0007 (18)
C11	0.040 (3)	0.034 (3)	0.027 (2)	0.001 (2)	0.010 (2)	−0.0020 (19)
C12	0.037 (3)	0.045 (3)	0.020 (2)	0.003 (2)	0.012 (2)	0.008 (2)
C13	0.026 (3)	0.028 (2)	0.0164 (19)	−0.0014 (19)	0.0057 (19)	0.0029 (17)
C14	0.028 (3)	0.028 (2)	0.019 (2)	0.002 (2)	0.0063 (19)	0.0017 (18)
C15	0.029 (3)	0.037 (3)	0.020 (2)	−0.002 (2)	0.008 (2)	0.001 (2)
C16	0.032 (3)	0.033 (3)	0.023 (2)	−0.002 (2)	0.007 (2)	0.0092 (18)
C17	0.033 (3)	0.026 (2)	0.028 (2)	−0.002 (2)	0.008 (2)	0.0022 (19)
C18	0.032 (3)	0.030 (2)	0.020 (2)	0.000 (2)	0.005 (2)	−0.0018 (18)
C19	0.025 (3)	0.025 (2)	0.019 (2)	−0.0012 (19)	0.0045 (19)	0.0013 (18)
C20	0.026 (2)	0.027 (2)	0.022 (2)	−0.0017 (19)	0.005 (2)	0.0033 (18)
C21	0.031 (3)	0.027 (2)	0.0177 (19)	−0.0022 (19)	0.0084 (19)	0.0035 (17)
C22	0.030 (3)	0.026 (2)	0.022 (2)	−0.0027 (19)	0.006 (2)	0.0013 (18)
C23	0.035 (3)	0.032 (3)	0.026 (2)	−0.002 (2)	0.005 (2)	−0.0026 (19)
C24	0.039 (3)	0.049 (3)	0.024 (2)	−0.002 (3)	0.016 (2)	0.007 (2)

O1—C10	1.24 (4)	C8—C9	1.42 (4)
O2—C10	1.311 (9)	C8—C10	1.48 (3)
O2—H2o	0.85 (6)	C11—H11a	0.96
O3—C2	1.35 (4)	C11—H11b	0.96
O3—C11	1.46 (2)	C11—H11c	0.96
O4—C3	1.367 (18)	C12—H12a	0.96
O4—C12	1.44 (2)	C12—H12b	0.96
O5—C22	1.24 (4)	C12—H12c	0.96
O6—C22	1.303 (9)	C13—C14	1.418 (15)
O6—H6o	0.85 (5)	C13—C18	1.41 (4)
O7—C14	1.36 (4)	C13—C19	1.45 (3)
O7—C23	1.45 (2)	C14—C15	1.40 (3)
O8—C15	1.373 (17)	C15—C16	1.38 (4)
O8—C24	1.43 (3)	C16—C17	1.391 (15)
N1—C9	1.16 (3)	C16—H16	0.96
N2—C21	1.15 (3)	C17—C18	1.37 (3)
C1—C2	1.411 (16)	C17—H17	0.96
C1—C6	1.40 (4)	C18—H18	0.96
C1—C7	1.45 (3)	C19—C20	1.364 (8)
C2—C3	1.41 (3)	C19—H19	0.96
C3—C4	1.37 (4)	C20—C21	1.43 (3)
C4—C5	1.394 (16)	C20—C22	1.48 (3)
C4—H4	0.96	C23—H23a	0.96
C5—C6	1.38 (3)	C23—H23b	0.96
C5—H5	0.96	C23—H23c	0.96
C6—H6	0.96	C24—H24a	0.96
C7—C8	1.362 (8)	C24—H24b	0.96
C7—H7	0.96	C24—H24c	0.96
C10—O2—H2o	109 (5)	H12a—C12—H12b	109.4706
C2—O3—C11	116.4 (14)	H12a—C12—H12c	109.4709
C3—O4—C12	118 (2)	H12b—C12—H12c	109.4715
C22—O6—H6o	98 (5)	C14—C13—C18	118.8 (17)
C14—O7—C23	116.3 (14)	C14—C13—C19	117 (2)
C15—O8—C24	118 (2)	C18—C13—C19	124.4 (11)
C2—C1—C6	119.1 (17)	O7—C14—C13	118.5 (17)
C2—C1—C7	117 (2)	O7—C14—C15	121.5 (12)
C6—C1—C7	124.4 (12)	C13—C14—C15	120 (2)
O3—C2—C1	119.3 (17)	O8—C15—C14	115 (2)
O3—C2—C3	121.0 (12)	O8—C15—C16	125.2 (18)
C1—C2—C3	120 (2)	C14—C15—C16	119.9 (12)
O4—C3—C2	115 (2)	C15—C16—C17	119.9 (18)
O4—C3—C4	125.3 (17)	C15—C16—H16	120.0398
C2—C3—C4	120.0 (12)	C17—C16—H16	120.0393
C3—C4—C5	120.3 (18)	C16—C17—C18	122 (3)
C3—C4—H4	119.845	C16—C17—H17	119.1935
C5—C4—H4	119.8442	C18—C17—H17	119.193
C4—C5—C6	121 (3)	C13—C18—C17	119.8 (13)
C4—C5—H5	119.6762	C13—C18—H18	120.1038
C6—C5—H5	119.6755	C17—C18—H18	120.1024
C1—C6—C5	120.4 (13)	C13—C19—C20	130 (2)
C1—C6—H6	119.8163	C13—C19—H19	115.0573
C5—C6—H6	119.8174	C20—C19—H19	115.0579
C1—C7—C8	131 (2)	C19—C20—C21	126 (2)
C1—C7—H7	114.6249	C19—C20—C22	119 (2)
C8—C7—H7	114.6246	C21—C20—C22	114.9 (9)
C7—C8—C9	125 (2)	N2—C21—C20	178.7 (18)
C7—C8—C10	119 (2)	O5—C22—O6	124 (2)
C9—C8—C10	116.0 (9)	O5—C22—C20	121.2 (9)
N1—C9—C8	177.1 (17)	O6—C22—C20	115 (2)
O1—C10—O2	124 (2)	O7—C23—H23a	109.4707
O1—C10—C8	121.9 (9)	O7—C23—H23b	109.4723
O2—C10—C8	115 (2)	O7—C23—H23c	109.472
O3—C11—H11a	109.4714	H23a—C23—H23b	109.4696
O3—C11—H11b	109.4709	H23a—C23—H23c	109.4705
O3—C11—H11c	109.4705	H23b—C23—H23c	109.4722
H11a—C11—H11b	109.4718	O8—C24—H24a	109.4715
H11a—C11—H11c	109.4715	O8—C24—H24b	109.4709
H11b—C11—H11c	109.4713	O8—C24—H24c	109.4717
O4—C12—H12a	109.471	H24a—C24—H24b	109.4707
O4—C12—H12b	109.4717	H24a—C24—H24c	109.4706
O4—C12—H12c	109.4716	H24b—C24—H24c	109.4718
C1—C2—O3—C11	−120.5 (7)	C13—C14—O7—C23	121.0 (7)
C2—C3—O4—C12	−178.0 (5)	C14—C15—O8—C24	177.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6o···O1i	0.85 (5)	1.82 (6)	2.62 (3)	154 (6)
O2—H2o···O5ii	0.85 (6)	1.79 (6)	2.63 (3)	169 (8)
C11—H11c···O4iii	0.96	2.56	3.50 (3)	167.
C23—H23a···O3iii	0.96	2.56	3.42 (4)	149.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6o⋯O1i	0.85 (5)	1.82 (6)	2.62 (3)	154 (6)
O2—H2o⋯O5ii	0.85 (6)	1.79 (6)	2.63 (3)	169 (8)
C11—H11c⋯O4iii	0.96	2.56	3.50 (3)	167
C23—H23a⋯O3iii	0.96	2.56	3.42 (4)	149

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