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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

3-Nitro­phenyl­acetic acid: a three-dimensional hydrogen-bonded framework structure containing sub­structures in zero, one and two dimensions

aInstituto de Tecnologia em Fármacos, Far-Manguinhos, FIOCRUZ, 21041-250 Rio de Janeiro, RJ, Brazil, bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, cDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and dSchool of Chemistry, University of St Andrews, Fife, KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 20 September 2006; accepted 25 September 2006; online 19 October 2006)

In the title compound, C8H7NO4, the mol­ecules are linked into a three-dimensional framework structure by a combination of O—H⋯O, C—H⋯O(carbonyl) and C—H⋯O(nitro) hydrogen bonds. Comparisons are made between the supra­molecular structures of the three isomeric nitro­phenyl­acetic acids.

Comment

We have recently reported the structure of 2-nitro­phenyl­acetic acid, (I)[link] (Wardell et al., 2006[Wardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. E62, o1915-o1917.]), and here we report the structure of the isomeric compound 3-nitro­phenyl­acetic acid, (II)[link]. The structure of 4-nitro­phenyl­acetic acid, (III)[link], was reported some years ago (Grabowski et al., 1990[Grabowski, S. J., Krygowski, T. M., Häfelinger, G. & Ritter, G. (1990). Acta Cryst. C46, 428-430.]), and the structure determination for (II)[link] now permits a comparison of all three isomers, (I)[link]–(III)[link].

[Scheme 1]

The exocyclic substituents in compound (II)[link] are both twisted out of the plane of the aryl ring (Fig. 1[link] and Table 1[link]), so that the mol­ecules are chiral. However, the space group accommodates equal numbers of the two enanti­omeric forms. The C—O bond distances are consistent with full ordering of the acidic H atom, as deduced from difference maps.

The mol­ecules of (II)[link] are linked by a combination of O—H⋯O, C—H⋯O(carbonyl) and C—H⋯O(nitro) hydrogen bonds (Table 2[link]) into a three-dimensional framework structure, whose formation is readily analysed in terms of a series of substructures of lower dimensionality: a finite zero-dimensional dimer unit, which can be regarded as the basic building unit within the structure, and two independent substructures, one of which is one-dimensional and the other of which is two-dimensional, which result from different modes of linkage of the dimers.

Hydroxyl atom O12 in the mol­ecule at (x, y, z) acts as hydrogen-bond donor to carbonyl atom O11 in the mol­ecule at (1 − x, −y, 1 − z), so generating by inversion a dimer characterized by the usual R22(8) (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) motif (Fig. 2[link]). This dimer can be regarded as the basic building unit within the structure, from which the other two substructures are built. The one-dimensional substructure involves a C—H⋯O(carbonyl) hydrogen bond: aryl atom C6 in the mol­ecule at (x, y, z), part of the dimer centred at ([{1 \over 2}], 0, [{1 \over 2}]), acts as hydrogen-bond donor to carbonyl atom O11 in the mol­ecule at (1 − x, y, [{3\over 2}] − z), which is part of the dimer centred at ([{1 \over 2}], 0, 1). Propagation by inversion and rotation then generates a chain of R22(8) rings generated by inversion alternating with R22(12) rings generated by rotation, running parallel to the [001] direction (Fig. 3[link]).

The two-dimensional substructure of compound (II)[link] involves a C—H⋯O(nitro) hydrogen bond. The aryl atoms C2 in the mol­ecules at (x, y, z) and (1 − x, −y, 1 − z), which comprise the R22(8) dimer centred at ([{1\over 2}], 0, [{1\over 2}]), act as hydrogen-bond donors to the nitro atoms O32 in the mol­ecules at ([{1\over 2}], − x, −[{1\over 2}] + y, [{1\over 2}] − z) and ([{1\over 2}] + x, [{1\over 2}] − y, [{1\over 2}] + z), respectively, which themselves form parts of the dimers centred at (0, −[{1\over 2}], 0) and (1, [{1\over 2}], 1). Similarly, nitro atoms O32 in the mol­ecules at (x, y, z) and (1 − x, −y, 1 − z) accept hydrogen bonds from atoms C2 in the mol­ecules at ([{1\over 2}] − x, [{1\over 2}] + y, [{1\over 2}] − z) and ([{1\over 2}] + x, −[{1\over 2}] − y, [{1\over 2}] + z), respectively, which form parts of the dimers centred at (0, [{1\over 2}], 0) and (1, −[{1\over 2}], 1). Hence, each dimer is linked in this manner to four adjacent dimers, and propagation of this C—H⋯O(nitro) hydrogen bond then generates a sheet parallel to (10[\overline{1}]) built of alternating R22(8) and R66(40) rings (Fig. 4[link]). The combination of [001] chains and (10[\overline{1}]) sheets suffices to generate a single continuous three-dimensional framework structure.

It is of inter­est to compare briefly the supra­molecular structure of (II)[link] with those of the two isomers, (I)[link] and (III)[link]. In 2-nitro­pheylacetic acid, (I)[link], the mol­ecules are linked into sheets of R22(8) and R44(18) rings by one O—H⋯O hydrogen bond and two independent C—H⋯O hydrogen bonds, both of which involve nitro O atoms as acceptors (Wardell et al., 2006[Wardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. E62, o1915-o1917.]). Thus, although the hydrogen bonds deployed in the structures of (I)[link] and (II)[link] are similar, differing principally in the identity of one of the acceptors, the dimensionality of the resulting structures differs. In 4-nitro­phenyl­acetic acid, (III)[link] (Grabowski et al., 1990[Grabowski, S. J., Krygowski, T. M., Häfelinger, G. & Ritter, G. (1990). Acta Cryst. C46, 428-430.]), the centrosymmetric R22(8) dimers are linked into sheets by an aromatic ππ stacking inter­action but, in contrast with the structures of (I)[link] and (II)[link], C—H⋯O hydrogen bonds are absent (Wardell et al., 2006[Wardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. E62, o1915-o1917.]). Hence, significant changes in the supra­molecular structures of isomers (I)[link]–(III)[link] result from a simple shift of a single substituent between the various sites on the aryl ring, posing a keen test for the predicta­bility of structures from first principles.

[Figure 1]
Figure 1
A mol­ecule of compound (II)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2]
Figure 2
Part of the crystal structure of (II)[link], showing the formation of an R22(8) dimer centred at ([{1\over 2}], 0, [{1\over 2}]). For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, −y, 1 − z).
[Figure 3]
Figure 3
A stereoview of part of the crystal structure of (II)[link], showing the formation of a chain of R22(8) and R22(12) rings along [001]. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
[Figure 4]
Figure 4
A stereoview of part of the crystal structure of (II)[link], showing the formation of a sheet of R22(8) and R66(40) rings parallel to (10[\overline{1}]). For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

Experimental

A commercial sample (Aldrich) of 3-nitro­phenyl­acetic acid was recrystallized from water.

Crystal data
  • C8H7NO4

  • Mr = 181.15

  • Monoclinic, C 2/c

  • a = 21.9690 (6) Å

  • b = 9.2901 (7) Å

  • c = 7.9642 (2) Å

  • β = 106.216 (2)°

  • V = 1560.78 (13) Å3

  • Z = 8

  • Dx = 1.542 Mg m−3

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 120 (2) K

  • Needle, colourless

  • 0.62 × 0.07 × 0.05 mm

Data collection
  • Bruker–Nonius KappaCCD area-detector diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.]) Tmin = 0.957, Tmax = 0.994

  • 16903 measured reflections

  • 1798 independent reflections

  • 1426 reflections with I > 2σ(I)

  • Rint = 0.041

  • θmax = 27.6°

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.108

  • S = 1.03

  • 1798 reflections

  • 119 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0605P)2 + 0.8287P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Selected geometric parameters (Å, °)

C12—O11 1.2194 (16)
C12—O12 1.3216 (15)
C2—C3—N3—O31 14.78 (17)
C2—C1—C11—C12 117.89 (13)
C1—C11—C12—O12 172.54 (11)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O12—H12⋯O11i 0.84 1.86 2.6980 (13) 175
C2—H2⋯O32ii 0.95 2.49 3.4099 (16) 164
C6—H6⋯O11iii 0.95 2.52 3.4474 (17) 166
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, y, [-z+{\script{3\over 2}}].

The systematic absences permitted Cc and C2/c as possible space groups; C2/c was selected and confirmed by the successful structure analysis. All H atoms were located in difference maps and then treated as riding atoms, with C—H distances of 0.95 (aromatic) or 0.99 Å (CH2) and O—H distances of 0.84 Å, and with UisoH = 1.2Ueq(C) or 1.5Ueq(O).

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supporting information


Comment top

We have recently reported the structure of 2-nitrophenylacetic acid, (I) (Wardell et al., 2006), and here we report the structure of the isomeric compound 3-nitrophenylacetic acid, (II). The structure of 4-nitrophenylacetic acid, (III), was reported some years ago (Grabowski et al., 1990), and the structure determination for (II) now permits a comparison of all three isomers, (I)–(III).

The exocyclic substituents in compound (II) are both twisted out of the plane of the aryl ring (Fig. 1, Table 1), so that the molecules are chiral. However, the space group accommodates equal numbers of the two enantiomeric forms. The C—O bond distances are consistent with full ordering of the acidic H atom, as deduced from difference maps.

The molecules of (II) are linked by a combination of O—H···O, CH···O(carbonyl) and CH···O(nitro) hydrogen bonds (Table 2) into a three-dimensional framework structure, whose formation is readily analysed in terms of a series of sub-structures of lower dimensionality: a finite zero-dimensional dimer unit, which can be regarded as the basic building unit within the structure, and two independent sub-structures, one of which is one-dimensional and the other of which is two-dimensional, which result from different modes of linkage of the dimers.

Hydroxyl atom O12 in the molecule at (x, y, z) acts as hydrogen-bond donor to carbonyl atom O11 in the molecule at (1 − x, −y, 1 − z), so generating by inversion a dimer characterized by the usual R22(8) (Bernstein et al., 1995) motif (Fig. 2). This dimer can be regarded as the basic building unit within the structure, from which the other two sub-structure are built. The one-dimensional sub-structure involves a CH···O(carbonyl) hydrogen bond: aryl atom C6 in the molecule at (x, y, z), part of the dimer centred at (1/2, 0, 1/2), acts as hydrogen-bond donor to carbonyl atom O11 in the molecule at (1 − x, y, 3/2 − z), which is part of the dimer centred at (1/2, 0, 1). Propagation by inversion and rotation then generates a chain of R22(8) rings generated by inversion alternating with R22(12) rings generated by rotation, running parallel to the [001] direction (Fig. 3).

The two-dimensional sub-structure of compound (II) involves a CH···O(nitro) hydrogen bond. The aryl atoms C2 in the molecules at (x, y, z) and (1 − x, −y, 1 − z), which comprise the R22(8) dimer centred at (1/2, 0, 1/2), act as hydrogen-bond donors to the nitro atoms O32 in the molecules at (1/2, − x, −1/2 + y, 1/2 − z) and (1/2 + x, 1/2 − y, 1/2 + z), respectively, which themselves form parts of the dimers centred at (0, −1/2, 0) and (1, 1/2, 1). Similarly, the nitro atoms O32 in the molecules at (x, y, z) and (1 − x, −y, 1 − z) accept hydrogen bonds from the atoms C2 in the molecules at (1/2 − x, 1/2 + y, 1/2 − z) and (1/2 + x, −1/2 − y, 1/2 + z), respectively, which form parts of the dimers centred at (0, 1/2, 0) and (1, −1/2, 1). Hence each dimer is linked in this manner to four adjacent dimers, and propagation of this CH···O(nitro) hydrogen bond then generates a sheet parallel to (101) built of alternating R22(8) and R66(40) rings (Fig. 4). The combination of [001] chains and (101) sheets suffices to generate a single and continuous three-dimensional framework structure.

It is of interest to compare briefly the supramolecular structure of (II) with those of the two isomers, (I) and (III). In 2-nitropheylacetic acid, (I), the molecules are linked into sheets of R22(8) and R44(18) rings by one O—H···O hydrogen bond and two independent C—H···O hydrogen bonds, both of which involve nitro O atoms as acceptors (Wardell et al., 2006). Thus, although the hydrogen bonds deployed in the structures of (I) and (II) are similar, differing principally in the identity of one of the acceptors, the dimensionality of the resulting structures differs. In 4-nitrophenylacetic acid, (III) (Grabowski et al., 1990), the centrosymmetric R22(8) dimers are linked into sheets by an aromatic ππ stacking interaction but, in contrast with the structures of (I) and (II), C—H···O hydrogen bonds are absent (Wardell et al., 2006). Hence significant changes in the supramolecular structures of isomers (I)–(III) result from a simple shift of a single substituent between the various sites on the aryl ring, posing a keen test for the predictability of structures from first principles.

Experimental top

A commercial sample (Aldrich) of 3-nitrophenylacetic acid was recrystallized from water.

Refinement top

The systematic absences permitted Cc and C2/c as possible space groups; C2/c was selected, and was confirmed by the successful structure analysis. All H atoms were located in difference maps and then treated as riding atoms, with C—H distances of 0.95 (aromatic) or 0.99 Å (CH2) and O—H distances of 0.84 Å, and with UisoH = 1.2Ueq(C) or 1.5Ueq(O).

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. A molecule of compound (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Part of the crystal structure of (II), showing the formation of an R22(8) dimer centred at (1/2, 0, 1/2). For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, −y, 1 − z).
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of (II), showing the formation of a chain of R22(8) and R22(12) rings along [001]. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of (II), showing the formation of a sheet of R22(8) and R66(40) rings parallel to (101). For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
3-Nitrophenylacetic acid top
Crystal data top
C8H7NO4F(000) = 752
Mr = 181.15Dx = 1.542 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1798 reflections
a = 21.9690 (6) Åθ = 2.4–27.6°
b = 9.2901 (7) ŵ = 0.13 mm1
c = 7.9642 (2) ÅT = 120 K
β = 106.216 (2)°Needle, colourless
V = 1560.78 (13) Å30.62 × 0.07 × 0.05 mm
Z = 8
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
1798 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode1426 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 9.091 pixels mm-1θmax = 27.6°, θmin = 2.4°
ϕ and ω scansh = 2828
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1212
Tmin = 0.957, Tmax = 0.994l = 109
16903 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0605P)2 + 0.8287P]
where P = (Fo2 + 2Fc2)/3
1798 reflections(Δ/σ)max < 0.001
119 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C8H7NO4V = 1560.78 (13) Å3
Mr = 181.15Z = 8
Monoclinic, C2/cMo Kα radiation
a = 21.9690 (6) ŵ = 0.13 mm1
b = 9.2901 (7) ÅT = 120 K
c = 7.9642 (2) Å0.62 × 0.07 × 0.05 mm
β = 106.216 (2)°
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
1798 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
1426 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.994Rint = 0.041
16903 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.03Δρmax = 0.23 e Å3
1798 reflectionsΔρmin = 0.26 e Å3
119 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O110.47049 (5)0.16282 (10)0.51651 (13)0.0268 (3)
O120.43311 (5)0.04557 (10)0.58490 (15)0.0323 (3)
O310.22765 (5)0.56092 (11)0.29531 (14)0.0331 (3)
O320.28282 (5)0.75666 (10)0.35972 (13)0.0289 (3)
N30.27493 (5)0.62691 (12)0.37843 (15)0.0230 (3)
C10.37313 (6)0.32274 (14)0.61287 (17)0.0206 (3)
C20.32437 (6)0.39825 (14)0.49749 (16)0.0202 (3)
C30.32499 (6)0.54757 (13)0.50499 (17)0.0200 (3)
C40.37157 (6)0.62561 (14)0.62303 (17)0.0219 (3)
C50.41941 (6)0.54895 (14)0.73923 (18)0.0237 (3)
C60.42016 (6)0.39950 (14)0.73416 (17)0.0219 (3)
C110.37434 (6)0.16061 (14)0.60971 (18)0.0238 (3)
C120.43087 (6)0.09578 (13)0.56546 (16)0.0205 (3)
H20.29130.34870.41530.024*
H40.37080.72780.62440.026*
H50.45190.59900.82280.028*
H60.45320.34860.81460.026*
H11A0.33540.12630.52320.029*
H11B0.37340.12460.72590.029*
H120.46440.07820.55610.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0286 (5)0.0167 (5)0.0395 (6)0.0009 (4)0.0169 (4)0.0001 (4)
O120.0315 (6)0.0152 (5)0.0572 (7)0.0026 (4)0.0240 (5)0.0032 (4)
O310.0257 (5)0.0283 (6)0.0403 (6)0.0008 (4)0.0010 (4)0.0007 (4)
O320.0345 (6)0.0182 (5)0.0370 (6)0.0031 (4)0.0152 (5)0.0065 (4)
N30.0252 (6)0.0196 (6)0.0272 (6)0.0034 (4)0.0121 (5)0.0022 (4)
C10.0201 (7)0.0184 (7)0.0269 (7)0.0014 (5)0.0127 (5)0.0000 (5)
C20.0183 (6)0.0188 (7)0.0257 (6)0.0012 (5)0.0098 (5)0.0015 (5)
C30.0201 (7)0.0182 (7)0.0245 (6)0.0024 (5)0.0110 (5)0.0023 (5)
C40.0242 (7)0.0151 (6)0.0305 (7)0.0012 (5)0.0144 (6)0.0015 (5)
C50.0212 (7)0.0233 (7)0.0281 (7)0.0014 (5)0.0094 (5)0.0053 (5)
C60.0189 (6)0.0230 (7)0.0253 (6)0.0025 (5)0.0086 (5)0.0004 (5)
C110.0218 (7)0.0166 (7)0.0345 (7)0.0006 (5)0.0102 (6)0.0016 (5)
C120.0223 (6)0.0153 (6)0.0227 (6)0.0002 (5)0.0044 (5)0.0003 (5)
Geometric parameters (Å, º) top
C1—C21.3908 (18)C4—H40.95
C1—C61.3971 (18)C5—C61.3893 (18)
C1—C111.5067 (18)C5—H50.95
C2—C31.3884 (17)C6—H60.95
C2—H20.95C11—C121.5079 (18)
C3—C41.3854 (18)C11—H11A0.99
C3—N31.4662 (17)C11—H11B0.99
N3—O311.2284 (15)C12—O111.2194 (16)
N3—O321.2327 (14)C12—O121.3216 (15)
C4—C51.3874 (19)O12—H120.84
C2—C1—C6118.94 (12)C4—C5—H5119.8
C2—C1—C11120.47 (12)C6—C5—H5119.8
C6—C1—C11120.57 (12)C5—C6—C1121.18 (12)
C3—C2—C1118.62 (12)C5—C6—H6119.4
C3—C2—H2120.7C1—C6—H6119.4
C1—C2—H2120.7C1—C11—C12115.01 (11)
C4—C3—C2123.27 (12)C1—C11—H11A108.5
C4—C3—N3118.26 (11)C12—C11—H11A108.5
C2—C3—N3118.44 (11)C1—C11—H11B108.5
O31—N3—O32123.31 (11)C12—C11—H11B108.5
O31—N3—C3118.60 (11)H11A—C11—H11B107.5
O32—N3—C3118.09 (11)O11—C12—O12122.58 (12)
C3—C4—C5117.54 (12)O11—C12—C11125.36 (12)
C3—C4—H4121.2O12—C12—C11112.06 (11)
C5—C4—H4121.2C12—O12—H12109.5
C4—C5—C6120.43 (12)
C6—C1—C2—C31.27 (18)N3—C3—C4—C5178.54 (11)
C11—C1—C2—C3179.88 (12)C3—C4—C5—C60.67 (18)
C1—C2—C3—C40.61 (19)C4—C5—C6—C10.00 (19)
C1—C2—C3—N3177.55 (11)C2—C1—C6—C51.00 (19)
C4—C3—N3—O31166.97 (12)C11—C1—C6—C5179.61 (12)
C2—C3—N3—O3114.78 (17)C2—C1—C11—C12117.89 (13)
C4—C3—N3—O3213.74 (17)C6—C1—C11—C1263.52 (16)
C2—C3—N3—O32164.51 (11)C1—C11—C12—O117.75 (19)
C2—C3—C4—C50.37 (19)C1—C11—C12—O12172.54 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O11i0.841.862.6980 (13)175
C2—H2···O32ii0.952.493.4099 (16)164
C6—H6···O11iii0.952.523.4474 (17)166
Symmetry codes: (i) x+1, y, z+1; (ii) x+1/2, y1/2, z+1/2; (iii) x+1, y, z+3/2.

Experimental details

Crystal data
Chemical formulaC8H7NO4
Mr181.15
Crystal system, space groupMonoclinic, C2/c
Temperature (K)120
a, b, c (Å)21.9690 (6), 9.2901 (7), 7.9642 (2)
β (°) 106.216 (2)
V3)1560.78 (13)
Z8
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.62 × 0.07 × 0.05
Data collection
DiffractometerBruker Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.957, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
16903, 1798, 1426
Rint0.041
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.108, 1.03
No. of reflections1798
No. of parameters119
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.26

Computer programs: COLLECT (Nonius, 1999), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
C12—O111.2194 (16)C12—O121.3216 (15)
C2—C3—N3—O3114.78 (17)C1—C11—C12—O12172.54 (11)
C2—C1—C11—C12117.89 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O11i0.841.862.6980 (13)175
C2—H2···O32ii0.952.493.4099 (16)164
C6—H6···O11iii0.952.523.4474 (17)166
Symmetry codes: (i) x+1, y, z+1; (ii) x+1/2, y1/2, z+1/2; (iii) x+1, y, z+3/2.
 

Acknowledgements

The X-ray data were collected at the EPSRC National Crystallography Service, University of Southampton, England; the authors thank the staff of the Service for all their help and advice.

References

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First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.  Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. E62, o1915–o1917.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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