Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages o3508-o3509
https://doi.org/10.1107/S1600536811051129

(E)-2-Cyano-3-(2,3-dimeth­­oxy­phen­yl)acrylic acid

Aliakbar Dehno Khalaji,a Karla Fejfarováb* and Michal Dušekb

aDepartment of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran, and bInstitute of Physics of the ASCR, v.v.i, Na Slovance 2, 182 21 Praha 8, Czech Republic
*Correspondence e-mail: fejfarov@fzu.cz

(Received 19 November 2011; accepted 28 November 2011; online 30 November 2011)

The asymmetric unit of the title compound, C12H11NO4, contains two mol­ecules. In the crystal, neighbouring mol­ecules 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 inter­actions [centroid–centroid distances = 3.856 (3) and 3.857 (3) Å]. The crystal structure is further stabilized by weak inter­molecular C—H⋯O inter­actions. 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[Hagberg, D. P., Edvinsson, T., Marinado, T., Boschloo, G., Hagfeldt, A. & Sun, L. (2006). Chem. Commun. pp. 2245-2247.]); Kim et al. (2008[Kim, D., Kang, M. S., Song, K., Kang, S. O. & Ko, J. (2008). Tetrahedron, 64, 10417-10424.]); Hara et al. (2003[Hara, K., Kurashige, M., Ito, S., Shinpo, A., Suga, S., Sayama, K. & Arakawa, H. (2003). Chem. Commun. pp. 252-253.]). For structures and properties of complexes based on carboxyl­ate ligands, see, for example: Zhao et al. (2008[Zhao, Y. H., Su, Z. M., Fu, Y. M., Shao, K. Z., Li, P., Wang, Y., Hao, X. R., Zhu, D. X. & Liu, S. D. (2008). Polyhedron, 27, 583-592.]); Wang et al. (2009[Wang, X. L., Chen, Y. Q., Liu, G. C., Lin, H. Y., Zheng, W. Y. & Zhang, J. X. (2009). J. Organomet. Chem. 694, 2263-2269.]); Mitra et al. (2006[Mitra, K., Mishra, D., Biswas, S., Lucas, C. R. & Adhikary, B. (2006). Polyhedron, 25, 1681-1688.]); Shit et al. (2009[Shit, S., Chakraborty, J., Samanta, B., Pilet, G. & Mitra, S. (2009). J. Mol. Struct. 919, 361-365.]); Akhbari et al. (2009[Akhbari, K., Alizadeh, K., Morsali, A. & Zeller, M. (2009). Inorg. Chim. Acta, 362, 2589-2594.]).

[Scheme 1]

Experimental

Crystal data

  • C12H11NO4

  • Mr = 233.2

  • Monoclinic, P 21

  • 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[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.525, Tmax = 1

  • 17777 measured reflections

  • 1922 independent reflections

  • 1638 reflections with I > 3σ(I)

  • Rint = 0.083
Refinement

  • R[F2 > 3σ(F2)] = 0.049

  • wR(F2) = 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

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) x, y, z+1; (ii) x, y, z-1; (iii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: JANA2006 (Petříček et al., 2006[Petříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and COOT (Emsley et al., 2010[Emsley, P., Lohkamp, B., Scott, W. G. & Cowtan, K. (2010). Acta Cryst. D66, 486-501.]); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811051129/bt5719sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811051129/bt5719Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811051129/bt5719Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S1600536811051129/bt5719Isup4.cml

checkCIF report


Comment top

Carboxylate compounds, an important family of O-donor ligands, can coordinate to different metal ions forming versatile structures with different topologies and stabilities (Zhao et al., 2008; Wang et al., 2009). Transition metal complexes with these ligands have special properties and applications (Mitra et al., 2006; Shit et al., 2009; Akhbari et al., 2009;). Among the carboxylate compounds, cyanoacrylic acid derivatives are of great importance to convert solar light into electricity in dye-sensitized solar cells (Hagberg et al., 2006; Kim et al., 2008 and Hara et al., 2003).

In consideration of the important applications of carboxylate compounds, herein the crystal structure of the title compound, (I), is reported. Systematic characterization of (I) has been performed by elemental analyses, FT—IR, 1H-NMR, UV-Vis spectroscopy and x-ray crystallography

The molecular structure of (I) with the atom-numbering scheme is presented in Fig. 1. The asymmetric unit of (I) contains two molecules, which differ mainly in the orientation of methoxy groups (Fig. 3) as reflected in the C1—C2—O3—C11 and C13—C14—O7—C23 torsion angles of -120.5 (7)° and 121.0 (7) °, respectively. In both molecules, the phenyl ring and the chain connecting the ring to the CN and COOH groups are nearly coplanar. The dihedral angles between the planes of the phenyl rings (C1–C6, C13–C18) and the planes defined by C7–C10 and C19–C22, are 5.7 (4)° and 5.5 (4) °, respectively. This degree of coplanarity allows for increased π-conjugation in the title compound.

Careful inspection of the packing diagram (Fig. 2) lead us to assumption that the two independent molecules could be related by non-crystallographic inversion center. To test this assumption, we used in the first step a rigid-body approach available in the crystallographic package JANA2006 (Petříček et al., 2006). The atoms of the first molecule (C1—C12, N1, O1–O4) were taken as a model molecule and refined to obtain the geometry of the model molecule. Together with the model molecule we refined a translation vector and three rotation angles transforming the model molecule to the actual position A (C1—C12, N1, O1–O4) and another translation vector and three rotation angles transforming the inverted model molecule to the actual position B (C13–C24, N2, O5–O7). The resulting R value was 5.2% for 164 refined parameters, providing evidence that the geometry of A and inverted geometry of B can be considered identical. In the second step, we graphically connected corresponding atoms in the two identical molecules A and B by lines (Fig. 4) to inspect visually position of the possible non-crystallographic inversion centre. The lines did not intersect at the same point but the obtained intersections were very close indicating that the inversion center is present only approximately. In order to quantify this finding in terms of R value we used the original structure model without rigid body (i.e. the one reported in this article) and we restricted the coordinates and ADP parameters of corresponding atoms of the two molecules by a local inversion symmetry operation located at the average position of the intersections shown in Fig. 4. Indeed, the resulting R value increased to 7.1% for 158 refined parameters.

In the crystal, the molecules form hydrogen-bonded dimers via the carboxyl groups. These dimers are connected by π-π interactions (centroid-centroid distances 3.856 (3), 3.857 (3) Å into columns parallel to the a axis (Fig. 2). The crystal structure is further stabilized by weak intermolecular C—H···O interactions.

The crystal studied was a non-merohedral twin with the ratio of the twin components of 0.657 (11):0.343 (11).

Related literature top

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 top

2,3-dimethoxybenzaldehyde (0.4 mmol) and cyanoacetic acid (0.4 mmol) were dissolved in a mixture of methanol:acetonitrile (1:1 v/v, 20 ml) in the presence of piperidine (0.4 mmol). The mixture was stirred and refluxed for 1.5 h to give a clear yellow solution. The mixture was cooled and the product was allowed to crystallize by slow evaporation technique at room temperature. After 5 days, yellow precipitate of (I) was formed which was collected by filtration and dried at room temperature. Recrystallization of the yellow precipitate from acetonitrile-chloroform mixture (2:1 v/v, 30 ml) by adding acetic acid afforded yellow crystals of 2-cyano-3-(2,5-dimethoxyphenyl)acrylic acid (1). Yield: 91%. Anal. Calc. for C12H11NO4: C, 61.80; H, 4.75; N, 6.01%. Found: C, 61.77; H, 4.79; N, 6.08%. FT—IR (KBr, cm-1): 2922–3059, 2839, 2220, 1697, 1678, 1571, 1497, 1469, 1458, 1425, 1381, 1364, 1297, 1248, 1234. UV–Vis, λmax (nm)/ε (M-1cm-1); 241 (9287), 310 (25074). 1H NMR (DMSO-d6): δ = 3.81 (s, 3H), 3.85 (s, 3H), 7.25 (t, 1H), 7.33 (dd, 1H), 7.71 (dd, 1H), 8.47 (s, 1H), 14.08 (b, 1H) p.p.m..

Refinement top

All H atoms bonded to carbon atoms were positioned geometrically and treated as riding on their parent atoms. The methyl H atoms were allowed to rotate freely about the adjacent C—O bonds. The carboxyl H atoms were found in difference Fourier maps and their coordinates were refined with restraint on the O—H bond length 0.85 Å with σ of 0.02. All H atoms were refined with displacement coefficients Uiso(H) set to 1.5Ueq(C, O) for the methyl and carboxyl groups and to to 1.2Ueq(C) for the CH-groups. As the structure contains only light atoms, Friedel pairs were merged and the Flack parameter value has not been determined.

Structure description top

Carboxylate compounds, an important family of O-donor ligands, can coordinate to different metal ions forming versatile structures with different topologies and stabilities (Zhao et al., 2008; Wang et al., 2009). Transition metal complexes with these ligands have special properties and applications (Mitra et al., 2006; Shit et al., 2009; Akhbari et al., 2009;). Among the carboxylate compounds, cyanoacrylic acid derivatives are of great importance to convert solar light into electricity in dye-sensitized solar cells (Hagberg et al., 2006; Kim et al., 2008 and Hara et al., 2003).

In consideration of the important applications of carboxylate compounds, herein the crystal structure of the title compound, (I), is reported. Systematic characterization of (I) has been performed by elemental analyses, FT—IR, 1H-NMR, UV-Vis spectroscopy and x-ray crystallography

The molecular structure of (I) with the atom-numbering scheme is presented in Fig. 1. The asymmetric unit of (I) contains two molecules, which differ mainly in the orientation of methoxy groups (Fig. 3) as reflected in the C1—C2—O3—C11 and C13—C14—O7—C23 torsion angles of -120.5 (7)° and 121.0 (7) °, respectively. In both molecules, the phenyl ring and the chain connecting the ring to the CN and COOH groups are nearly coplanar. The dihedral angles between the planes of the phenyl rings (C1–C6, C13–C18) and the planes defined by C7–C10 and C19–C22, are 5.7 (4)° and 5.5 (4) °, respectively. This degree of coplanarity allows for increased π-conjugation in the title compound.

Careful inspection of the packing diagram (Fig. 2) lead us to assumption that the two independent molecules could be related by non-crystallographic inversion center. To test this assumption, we used in the first step a rigid-body approach available in the crystallographic package JANA2006 (Petříček et al., 2006). The atoms of the first molecule (C1—C12, N1, O1–O4) were taken as a model molecule and refined to obtain the geometry of the model molecule. Together with the model molecule we refined a translation vector and three rotation angles transforming the model molecule to the actual position A (C1—C12, N1, O1–O4) and another translation vector and three rotation angles transforming the inverted model molecule to the actual position B (C13–C24, N2, O5–O7). The resulting R value was 5.2% for 164 refined parameters, providing evidence that the geometry of A and inverted geometry of B can be considered identical. In the second step, we graphically connected corresponding atoms in the two identical molecules A and B by lines (Fig. 4) to inspect visually position of the possible non-crystallographic inversion centre. The lines did not intersect at the same point but the obtained intersections were very close indicating that the inversion center is present only approximately. In order to quantify this finding in terms of R value we used the original structure model without rigid body (i.e. the one reported in this article) and we restricted the coordinates and ADP parameters of corresponding atoms of the two molecules by a local inversion symmetry operation located at the average position of the intersections shown in Fig. 4. Indeed, the resulting R value increased to 7.1% for 158 refined parameters.

In the crystal, the molecules form hydrogen-bonded dimers via the carboxyl groups. These dimers are connected by π-π interactions (centroid-centroid distances 3.856 (3), 3.857 (3) Å into columns parallel to the a axis (Fig. 2). The crystal structure is further stabilized by weak intermolecular C—H···O interactions.

The crystal studied was a non-merohedral twin with the ratio of the twin components of 0.657 (11):0.343 (11).

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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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 (Petříček et al., 2006).

Figures top
[Figure 1] Fig. 1. The structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound, viewed along the c axis. Hydrogen bonds are drawn as blue dashed lines, π-π interactions as red dashed lines. Hydrogen atoms not participating in hydrogen bonds were omitted for clarity.
[Figure 3] Fig. 3. Overlay of two molecules present in asymmetric unit. Red: C1—C12, N1, O1–O4, blue: C13–C24, N2, O5–O7. Hydrogen atoms are omitted for clarity.
[Figure 4] Fig. 4. Visual inspection of a possible non-crystallographic inversion center. The lines are connecting corresponding atoms of the two molecules.
(E)-2-Cyano-3-(2,3-dimethoxyphenyl)acrylic acid top
Crystal data top
C12H11NO4F(000) = 488
Mr = 233.2Dx = 1.433 Mg m−3
Monoclinic, P21Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ybCell parameters from 10329 reflections
a = 3.8564 (5) Åθ = 3.2–67.0°
b = 27.178 (3) ŵ = 0.92 mm−1
c = 10.4681 (9) ÅT = 120 K
β = 99.966 (9)°Plate, yellow
V = 1080.6 (2) Å30.57 × 0.15 × 0.05 mm
Z = 4
Data collection top
Agilent Xcalibur
diffractometer with an Atlas (Gemini ultra Cu) detector		1922 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source1638 reflections with I > 3σ(I)
Mirror monochromatorRint = 0.083
Detector resolution: 10.3784 pixels mm-1θmax = 67.2°, θmin = 3.3°
Rotation method data acquisition using ω scansh = −4→4
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)		k = −32→32
Tmin = 0.525, Tmax = 1l = −12→12
17777 measured reflections
Refinement top
Refinement on F283 constraints
R[F > 3σ(F)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F) = 0.129Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0025000002I2]
S = 1.73(Δ/σ)max = 0.005
1922 reflectionsΔρmax = 0.23 e Å−3
314 parametersΔρmin = −0.23 e Å−3
2 restraints
Crystal data top
C12H11NO4V = 1080.6 (2) Å3
Mr = 233.2Z = 4
Monoclinic, P21Cu Kα radiation
a = 3.8564 (5) ŵ = 0.92 mm−1
b = 27.178 (3) ÅT = 120 K
c = 10.4681 (9) Å0.57 × 0.15 × 0.05 mm
β = 99.966 (9)°
Data collection top
Agilent Xcalibur
diffractometer with an Atlas (Gemini ultra Cu) detector		1922 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)		1638 reflections with I > 3σ(I)
Tmin = 0.525, Tmax = 1Rint = 0.083
17777 measured reflections
Refinement top
R[F > 3σ(F)] = 0.0492 restraints
wR(F) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.73Δρmax = 0.23 e Å−3
1922 reflectionsΔρmin = −0.23 e Å−3
314 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2649 (11)0.6335 (11)0.4130 (3)0.0326 (11)
O20.4957 (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)
O50.5833 (10)0.6646 (11)1.1452 (3)0.0320 (12)
O60.3472 (10)0.7133 (11)1.2816 (3)0.0332 (12)
O70.8594 (9)0.7170 (11)0.7627 (3)0.0283 (10)
O80.9534 (10)0.7793 (11)0.5719 (3)0.0342 (12)
N10.5464 (13)0.4678 (11)0.3684 (4)0.0343 (14)
N20.2837 (13)0.8295 (11)1.1899 (4)0.0321 (14)
C10.1528 (12)0.5171 (11)0.6702 (5)0.0236 (14)
C20.0453 (13)0.5351 (11)0.7835 (4)0.0236 (14)
C3−0.0160 (12)0.5019 (11)0.8808 (4)0.0245 (14)
C40.0298 (13)0.4524 (11)0.8650 (4)0.0255 (14)
C50.1332 (14)0.4346 (11)0.7525 (5)0.0288 (15)
C60.1917 (13)0.4663 (11)0.6560 (4)0.0274 (15)
C70.2100 (13)0.5534 (11)0.5742 (4)0.0250 (14)
C80.3328 (14)0.5483 (11)0.4605 (4)0.0243 (14)
C90.4445 (14)0.5034 (11)0.4110 (4)0.0277 (14)
C100.3636 (13)0.5926 (11)0.3818 (4)0.0257 (14)
C110.1964 (15)0.6094 (11)0.9025 (5)0.0332 (16)
C12−0.1818 (14)0.4919 (11)1.0900 (5)0.0334 (16)
C130.6801 (13)0.7825 (11)0.8888 (4)0.0234 (13)
C140.7893 (13)0.7657 (11)0.7738 (4)0.0247 (14)
C150.8358 (13)0.7994 (11)0.6769 (4)0.0283 (15)
C160.7721 (14)0.8488 (11)0.6932 (5)0.0289 (15)
C170.6679 (14)0.8651 (11)0.8067 (5)0.0286 (15)
C180.6238 (13)0.8332 (11)0.9037 (4)0.0273 (15)
C190.6324 (13)0.7453 (11)0.9840 (4)0.0229 (14)
C200.5098 (13)0.7499 (11)1.0980 (4)0.0250 (14)
C210.3867 (13)0.7943 (11)1.1482 (4)0.0249 (14)
C220.4825 (13)0.7055 (11)1.1777 (4)0.0255 (14)
C230.6528 (14)0.6915 (11)0.6539 (5)0.0311 (15)
C240.9902 (15)0.8114 (11)0.4668 (5)0.0357 (17)
H4−0.009490.4298840.9317650.0306*
H50.1640090.3998160.7423120.0346*
H60.2594320.4535040.5784060.0329*
H70.1514050.5865160.5942590.03*
H11a0.276460.6401830.8730920.0498*
H11b0.057230.6154350.9685290.0498*
H11c0.3957510.5894490.9373030.0498*
H12a−0.2771460.5108251.1531050.0501*
H12b−0.3439340.4662121.0570650.0501*
H12c0.0381470.477571.1297840.0501*
H160.7998550.8719380.6263280.0347*
H170.625840.8995640.8172530.0344*
H180.5546050.8453650.9816460.0327*
H190.6970520.7125240.9634760.0275*
H23a0.6683170.6566250.6689730.0466*
H23b0.4113610.701660.6446080.0466*
H23c0.7417020.6991780.5761180.0466*
H24a1.0671130.7928050.3988810.0535*
H24b0.7675560.8265190.4341140.0535*
H24c1.1607340.8364080.4968160.0535*
H6o0.315 (19)0.6834 (14)1.301 (7)0.0498*
H2o0.50 (2)0.6115 (17)0.235 (6)0.0517*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.051 (2)0.0260 (17)0.0237 (16)−0.0015 (15)0.0152 (16)0.0005 (13)
O20.053 (2)0.0316 (19)0.0222 (16)−0.0003 (18)0.0166 (16)0.0036 (14)
O30.039 (2)0.0282 (17)0.0183 (14)0.0052 (15)0.0074 (14)0.0006 (13)
O40.042 (2)0.0356 (18)0.0183 (15)0.0008 (16)0.0162 (15)0.0033 (13)
O50.048 (2)0.0256 (18)0.0249 (18)0.0029 (15)0.0118 (16)0.0038 (13)
O60.047 (2)0.0329 (19)0.0238 (16)0.0009 (17)0.0181 (16)0.0038 (14)
O70.037 (2)0.0304 (18)0.0177 (14)0.0057 (14)0.0058 (14)−0.0018 (13)
O80.046 (2)0.042 (2)0.0183 (16)0.0056 (18)0.0151 (16)0.0045 (14)
N10.046 (3)0.036 (2)0.0238 (19)0.000 (2)0.0145 (19)−0.0008 (17)
N20.041 (3)0.032 (2)0.026 (2)−0.0008 (19)0.0129 (19)−0.0004 (17)
C10.022 (2)0.029 (2)0.021 (2)0.0003 (19)0.0066 (18)0.0038 (18)
C20.022 (2)0.028 (2)0.021 (2)0.0016 (18)0.0043 (19)0.0002 (18)
C30.023 (2)0.036 (2)0.017 (2)0.0012 (19)0.0094 (18)0.0015 (19)
C40.026 (2)0.031 (2)0.020 (2)−0.0031 (19)0.0053 (19)0.0032 (17)
C50.035 (3)0.029 (2)0.023 (2)−0.002 (2)0.008 (2)0.0023 (18)
C60.032 (3)0.030 (2)0.022 (2)−0.001 (2)0.009 (2)−0.0003 (19)
C70.028 (3)0.028 (2)0.020 (2)−0.0008 (19)0.0069 (19)0.0026 (18)
C80.028 (3)0.027 (2)0.018 (2)−0.0036 (19)0.0045 (19)−0.0008 (17)
C90.035 (3)0.028 (2)0.020 (2)−0.004 (2)0.007 (2)0.0008 (18)
C100.030 (3)0.030 (3)0.018 (2)−0.0027 (19)0.0073 (19)0.0007 (18)
C110.040 (3)0.034 (3)0.027 (2)0.001 (2)0.010 (2)−0.0020 (19)
C120.037 (3)0.045 (3)0.020 (2)0.003 (2)0.012 (2)0.008 (2)
C130.026 (3)0.028 (2)0.0164 (19)−0.0014 (19)0.0057 (19)0.0029 (17)
C140.028 (3)0.028 (2)0.019 (2)0.002 (2)0.0063 (19)0.0017 (18)
C150.029 (3)0.037 (3)0.020 (2)−0.002 (2)0.008 (2)0.001 (2)
C160.032 (3)0.033 (3)0.023 (2)−0.002 (2)0.007 (2)0.0092 (18)
C170.033 (3)0.026 (2)0.028 (2)−0.002 (2)0.008 (2)0.0022 (19)
C180.032 (3)0.030 (2)0.020 (2)0.000 (2)0.005 (2)−0.0018 (18)
C190.025 (3)0.025 (2)0.019 (2)−0.0012 (19)0.0045 (19)0.0013 (18)
C200.026 (2)0.027 (2)0.022 (2)−0.0017 (19)0.005 (2)0.0033 (18)
C210.031 (3)0.027 (2)0.0177 (19)−0.0022 (19)0.0084 (19)0.0035 (17)
C220.030 (3)0.026 (2)0.022 (2)−0.0027 (19)0.006 (2)0.0013 (18)
C230.035 (3)0.032 (3)0.026 (2)−0.002 (2)0.005 (2)−0.0026 (19)
C240.039 (3)0.049 (3)0.024 (2)−0.002 (3)0.016 (2)0.007 (2)
Geometric parameters (Å, º) top
O1—C101.24 (4)C8—C91.42 (4)
O2—C101.311 (9)C8—C101.48 (3)
O2—H2o0.85 (6)C11—H11a0.96
O3—C21.35 (4)C11—H11b0.96
O3—C111.46 (2)C11—H11c0.96
O4—C31.367 (18)C12—H12a0.96
O4—C121.44 (2)C12—H12b0.96
O5—C221.24 (4)C12—H12c0.96
O6—C221.303 (9)C13—C141.418 (15)
O6—H6o0.85 (5)C13—C181.41 (4)
O7—C141.36 (4)C13—C191.45 (3)
O7—C231.45 (2)C14—C151.40 (3)
O8—C151.373 (17)C15—C161.38 (4)
O8—C241.43 (3)C16—C171.391 (15)
N1—C91.16 (3)C16—H160.96
N2—C211.15 (3)C17—C181.37 (3)
C1—C21.411 (16)C17—H170.96
C1—C61.40 (4)C18—H180.96
C1—C71.45 (3)C19—C201.364 (8)
C2—C31.41 (3)C19—H190.96
C3—C41.37 (4)C20—C211.43 (3)
C4—C51.394 (16)C20—C221.48 (3)
C4—H40.96C23—H23a0.96
C5—C61.38 (3)C23—H23b0.96
C5—H50.96C23—H23c0.96
C6—H60.96C24—H24a0.96
C7—C81.362 (8)C24—H24b0.96
C7—H70.96C24—H24c0.96
C10—O2—H2o109 (5)H12a—C12—H12b109.4706
C2—O3—C11116.4 (14)H12a—C12—H12c109.4709
C3—O4—C12118 (2)H12b—C12—H12c109.4715
C22—O6—H6o98 (5)C14—C13—C18118.8 (17)
C14—O7—C23116.3 (14)C14—C13—C19117 (2)
C15—O8—C24118 (2)C18—C13—C19124.4 (11)
C2—C1—C6119.1 (17)O7—C14—C13118.5 (17)
C2—C1—C7117 (2)O7—C14—C15121.5 (12)
C6—C1—C7124.4 (12)C13—C14—C15120 (2)
O3—C2—C1119.3 (17)O8—C15—C14115 (2)
O3—C2—C3121.0 (12)O8—C15—C16125.2 (18)
C1—C2—C3120 (2)C14—C15—C16119.9 (12)
O4—C3—C2115 (2)C15—C16—C17119.9 (18)
O4—C3—C4125.3 (17)C15—C16—H16120.0398
C2—C3—C4120.0 (12)C17—C16—H16120.0393
C3—C4—C5120.3 (18)C16—C17—C18122 (3)
C3—C4—H4119.845C16—C17—H17119.1935
C5—C4—H4119.8442C18—C17—H17119.193
C4—C5—C6121 (3)C13—C18—C17119.8 (13)
C4—C5—H5119.6762C13—C18—H18120.1038
C6—C5—H5119.6755C17—C18—H18120.1024
C1—C6—C5120.4 (13)C13—C19—C20130 (2)
C1—C6—H6119.8163C13—C19—H19115.0573
C5—C6—H6119.8174C20—C19—H19115.0579
C1—C7—C8131 (2)C19—C20—C21126 (2)
C1—C7—H7114.6249C19—C20—C22119 (2)
C8—C7—H7114.6246C21—C20—C22114.9 (9)
C7—C8—C9125 (2)N2—C21—C20178.7 (18)
C7—C8—C10119 (2)O5—C22—O6124 (2)
C9—C8—C10116.0 (9)O5—C22—C20121.2 (9)
N1—C9—C8177.1 (17)O6—C22—C20115 (2)
O1—C10—O2124 (2)O7—C23—H23a109.4707
O1—C10—C8121.9 (9)O7—C23—H23b109.4723
O2—C10—C8115 (2)O7—C23—H23c109.472
O3—C11—H11a109.4714H23a—C23—H23b109.4696
O3—C11—H11b109.4709H23a—C23—H23c109.4705
O3—C11—H11c109.4705H23b—C23—H23c109.4722
H11a—C11—H11b109.4718O8—C24—H24a109.4715
H11a—C11—H11c109.4715O8—C24—H24b109.4709
H11b—C11—H11c109.4713O8—C24—H24c109.4717
O4—C12—H12a109.471H24a—C24—H24b109.4707
O4—C12—H12b109.4717H24a—C24—H24c109.4706
O4—C12—H12c109.4716H24b—C24—H24c109.4718
C1—C2—O3—C11−120.5 (7)C13—C14—O7—C23121.0 (7)
C2—C3—O4—C12−178.0 (5)C14—C15—O8—C24177.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6o···O1i0.85 (5)1.82 (6)2.62 (3)154 (6)
O2—H2o···O5ii0.85 (6)1.79 (6)2.63 (3)169 (8)
C11—H11c···O4iii0.962.563.50 (3)167
C23—H23a···O3iii0.962.563.42 (4)149
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC12H11NO4
Mr233.2
Crystal system, space groupMonoclinic, P21
Temperature (K)120
a, b, c (Å)3.8564 (5), 27.178 (3), 10.4681 (9)
β (°) 99.966 (9)
V (Å3)1080.6 (2)
Z4
Radiation typeCu Kα
µ (mm−1)0.92
Crystal size (mm)0.57 × 0.15 × 0.05
Data collection
DiffractometerAgilent Xcalibur
diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.525, 1
No. of measured, independent and
observed [I > 3σ(I)] reflections		17777, 1922, 1638
Rint0.083
(sin θ/λ)max (Å−1)0.598
Refinement
R[F > 3σ(F)], wR(F), S 0.049, 0.129, 1.73
No. of reflections1922
No. of parameters314
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.23, −0.23

Computer programs: CrysAlis PRO (Agilent, 2010), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005) and COOT (Emsley et al., 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6o···O1i0.85 (5)1.82 (6)2.62 (3)154 (6)
O2—H2o···O5ii0.85 (6)1.79 (6)2.63 (3)169 (8)
C11—H11c···O4iii0.962.563.50 (3)166.68
C23—H23a···O3iii0.962.563.42 (4)148.94
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (iii) x+1, y, z.
 

Acknowledgements

We acknowledge Golestan University and the Islamic Azad University, Qaemshahr, for partial support of this work, and the Institutional Research Plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae Project of the Academy of Sciences of the Czech Republic.

References

First citationAgilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
 First citationAkhbari, K., Alizadeh, K., Morsali, A. & Zeller, M. (2009). Inorg. Chim. Acta, 362, 2589–2594.  Web of Science CSD CrossRef CAS Google Scholar
 First citationBrandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBurla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  CrossRef IUCr Journals Google Scholar
 First citationEmsley, P., Lohkamp, B., Scott, W. G. & Cowtan, K. (2010). Acta Cryst. D66, 486–501.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationHagberg, D. P., Edvinsson, T., Marinado, T., Boschloo, G., Hagfeldt, A. & Sun, L. (2006). Chem. Commun. pp. 2245–2247.  Web of Science CrossRef Google Scholar
 First citationHara, K., Kurashige, M., Ito, S., Shinpo, A., Suga, S., Sayama, K. & Arakawa, H. (2003). Chem. Commun. pp. 252–253.  Web of Science CrossRef Google Scholar
 First citationKim, D., Kang, M. S., Song, K., Kang, S. O. & Ko, J. (2008). Tetrahedron, 64, 10417–10424.  Web of Science CrossRef CAS Google Scholar
 First citationMitra, K., Mishra, D., Biswas, S., Lucas, C. R. & Adhikary, B. (2006). Polyhedron, 25, 1681–1688.  Web of Science CSD CrossRef CAS Google Scholar
 First citationPetříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.  Google Scholar
 First citationShit, S., Chakraborty, J., Samanta, B., Pilet, G. & Mitra, S. (2009). J. Mol. Struct. 919, 361–365.  CrossRef CAS Google Scholar
 First citationWang, X. L., Chen, Y. Q., Liu, G. C., Lin, H. Y., Zheng, W. Y. & Zhang, J. X. (2009). J. Organomet. Chem. 694, 2263–2269.  Web of Science CSD CrossRef CAS Google Scholar
 First citationZhao, Y. H., Su, Z. M., Fu, Y. M., Shao, K. Z., Li, P., Wang, Y., Hao, X. R., Zhu, D. X. & Liu, S. D. (2008). Polyhedron, 27, 583–592.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages o3508-o3509
https://doi.org/10.1107/S1600536811051129
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS