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

Wardell, S.M.S.V.; Wardell, J.L.; Low, J.N.; Glidewell, C.

doi:10.1107/S0108270106039205

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 62| Part 11| November 2006| Pages o647-o649

doi:10.1107/S0108270106039205

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

Solange M. S. V. Wardell,^a James L. Wardell,^b John N. Low ^c and Christopher Glidewell ^d ^*

^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) (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 and 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, C—H⋯O(carbonyl) and C—H⋯O(nitro) hydrogen bonds (Table 2) 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 ) motif (Fig. 2). 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).

The two-dimensional substructure of compound (II) 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). 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) 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 π–π 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.

Figure 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
Part of the crystal structure of (II)

, 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
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
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 (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
M_r = 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
D_x = 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 ) T_min = 0.957, T_max = 0.994
16903 measured reflections
1798 independent reflections
1426 reflections with I > 2σ(I)
R_int = 0.041
θ_max = 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(F_o²) + (0.0605P)² + 0.8287P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.23 e Å⁻³
Δρ_min = −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	D⋯A	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 U_isoH = 1.2U_eq(C) or 1.5U_eq(O).

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 ).

Supporting information

Crystal structure: contains datablocks global, II. DOI: 10.1107/S0108270106039205/sk3059sup1.cif

Structure factors: contains datablock II. DOI: 10.1107/S0108270106039205/sk3059IIsup2.hkl

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, C—H···O(carbonyl) and C—H···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 C—H···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 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 (1/2, 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 C—H···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 π–π 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.

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

	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.
	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).
	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.
	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

C₈H₇NO₄	F(000) = 752
M_r = 181.15	D_x = 1.542 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1798 reflections
a = 21.9690 (6) Å	θ = 2.4–27.6°
b = 9.2901 (7) Å	µ = 0.13 mm⁻¹
c = 7.9642 (2) Å	T = 120 K
β = 106.216 (2)°	Needle, colourless
V = 1560.78 (13) Å³	0.62 × 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 anode	1426 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.6°, θ_min = 2.4°
ϕ and ω scans	h = −28→28
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −12→12
T_min = 0.957, T_max = 0.994	l = −10→9
16903 measured reflections

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0605P)² + 0.8287P] where P = (F_o² + 2F_c²)/3
1798 reflections	(Δ/σ)_max < 0.001
119 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₈H₇NO₄	V = 1560.78 (13) Å³
M_r = 181.15	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.9690 (6) Å	µ = 0.13 mm⁻¹
b = 9.2901 (7) Å	T = 120 K
c = 7.9642 (2) Å	0.62 × 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)
T_min = 0.957, T_max = 0.994	R_int = 0.041
16903 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	Δρ_max = 0.23 e Å⁻³
1798 reflections	Δρ_min = −0.26 e Å⁻³
119 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O11	0.47049 (5)	0.16282 (10)	0.51651 (13)	0.0268 (3)
O12	0.43311 (5)	−0.04557 (10)	0.58490 (15)	0.0323 (3)
O31	0.22765 (5)	0.56092 (11)	0.29531 (14)	0.0331 (3)
O32	0.28282 (5)	0.75666 (10)	0.35972 (13)	0.0289 (3)
N3	0.27493 (5)	0.62691 (12)	0.37843 (15)	0.0230 (3)
C1	0.37313 (6)	0.32274 (14)	0.61287 (17)	0.0206 (3)
C2	0.32437 (6)	0.39825 (14)	0.49749 (16)	0.0202 (3)
C3	0.32499 (6)	0.54757 (13)	0.50499 (17)	0.0200 (3)
C4	0.37157 (6)	0.62561 (14)	0.62303 (17)	0.0219 (3)
C5	0.41941 (6)	0.54895 (14)	0.73923 (18)	0.0237 (3)
C6	0.42016 (6)	0.39950 (14)	0.73416 (17)	0.0219 (3)
C11	0.37434 (6)	0.16061 (14)	0.60971 (18)	0.0238 (3)
C12	0.43087 (6)	0.09578 (13)	0.56546 (16)	0.0205 (3)
H2	0.2913	0.3487	0.4153	0.024*
H4	0.3708	0.7278	0.6244	0.026*
H5	0.4519	0.5990	0.8228	0.028*
H6	0.4532	0.3486	0.8146	0.026*
H11A	0.3354	0.1263	0.5232	0.029*
H11B	0.3734	0.1246	0.7259	0.029*
H12	0.4644	−0.0782	0.5561	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0286 (5)	0.0167 (5)	0.0395 (6)	0.0009 (4)	0.0169 (4)	0.0001 (4)
O12	0.0315 (6)	0.0152 (5)	0.0572 (7)	0.0026 (4)	0.0240 (5)	0.0032 (4)
O31	0.0257 (5)	0.0283 (6)	0.0403 (6)	0.0008 (4)	0.0010 (4)	0.0007 (4)
O32	0.0345 (6)	0.0182 (5)	0.0370 (6)	0.0031 (4)	0.0152 (5)	0.0065 (4)
N3	0.0252 (6)	0.0196 (6)	0.0272 (6)	0.0034 (4)	0.0121 (5)	0.0022 (4)
C1	0.0201 (7)	0.0184 (7)	0.0269 (7)	0.0014 (5)	0.0127 (5)	0.0000 (5)
C2	0.0183 (6)	0.0188 (7)	0.0257 (6)	−0.0012 (5)	0.0098 (5)	−0.0015 (5)
C3	0.0201 (7)	0.0182 (7)	0.0245 (6)	0.0024 (5)	0.0110 (5)	0.0023 (5)
C4	0.0242 (7)	0.0151 (6)	0.0305 (7)	−0.0012 (5)	0.0144 (6)	−0.0015 (5)
C5	0.0212 (7)	0.0233 (7)	0.0281 (7)	−0.0014 (5)	0.0094 (5)	−0.0053 (5)
C6	0.0189 (6)	0.0230 (7)	0.0253 (6)	0.0025 (5)	0.0086 (5)	−0.0004 (5)
C11	0.0218 (7)	0.0166 (7)	0.0345 (7)	0.0006 (5)	0.0102 (6)	0.0016 (5)
C12	0.0223 (6)	0.0153 (6)	0.0227 (6)	0.0002 (5)	0.0044 (5)	−0.0003 (5)

Geometric parameters (Å, º) top

C1—C2	1.3908 (18)	C4—H4	0.95
C1—C6	1.3971 (18)	C5—C6	1.3893 (18)
C1—C11	1.5067 (18)	C5—H5	0.95
C2—C3	1.3884 (17)	C6—H6	0.95
C2—H2	0.95	C11—C12	1.5079 (18)
C3—C4	1.3854 (18)	C11—H11A	0.99
C3—N3	1.4662 (17)	C11—H11B	0.99
N3—O31	1.2284 (15)	C12—O11	1.2194 (16)
N3—O32	1.2327 (14)	C12—O12	1.3216 (15)
C4—C5	1.3874 (19)	O12—H12	0.84

C2—C1—C6	118.94 (12)	C4—C5—H5	119.8
C2—C1—C11	120.47 (12)	C6—C5—H5	119.8
C6—C1—C11	120.57 (12)	C5—C6—C1	121.18 (12)
C3—C2—C1	118.62 (12)	C5—C6—H6	119.4
C3—C2—H2	120.7	C1—C6—H6	119.4
C1—C2—H2	120.7	C1—C11—C12	115.01 (11)
C4—C3—C2	123.27 (12)	C1—C11—H11A	108.5
C4—C3—N3	118.26 (11)	C12—C11—H11A	108.5
C2—C3—N3	118.44 (11)	C1—C11—H11B	108.5
O31—N3—O32	123.31 (11)	C12—C11—H11B	108.5
O31—N3—C3	118.60 (11)	H11A—C11—H11B	107.5
O32—N3—C3	118.09 (11)	O11—C12—O12	122.58 (12)
C3—C4—C5	117.54 (12)	O11—C12—C11	125.36 (12)
C3—C4—H4	121.2	O12—C12—C11	112.06 (11)
C5—C4—H4	121.2	C12—O12—H12	109.5
C4—C5—C6	120.43 (12)

C6—C1—C2—C3	1.27 (18)	N3—C3—C4—C5	−178.54 (11)
C11—C1—C2—C3	179.88 (12)	C3—C4—C5—C6	0.67 (18)
C1—C2—C3—C4	−0.61 (19)	C4—C5—C6—C1	0.00 (19)
C1—C2—C3—N3	177.55 (11)	C2—C1—C6—C5	−1.00 (19)
C4—C3—N3—O31	−166.97 (12)	C11—C1—C6—C5	−179.61 (12)
C2—C3—N3—O31	14.78 (17)	C2—C1—C11—C12	117.89 (13)
C4—C3—N3—O32	13.74 (17)	C6—C1—C11—C12	−63.52 (16)
C2—C3—N3—O32	−164.51 (11)	C1—C11—C12—O11	−7.75 (19)
C2—C3—C4—C5	−0.37 (19)	C1—C11—C12—O12	172.54 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, y−1/2, −z+1/2; (iii) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₈H₇NO₄
M_r	181.15
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	120
a, b, c (Å)	21.9690 (6), 9.2901 (7), 7.9642 (2)
β (°)	106.216 (2)
V (Å³)	1560.78 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.62 × 0.07 × 0.05

Data collection
Diffractometer	Bruker Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.957, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	16903, 1798, 1426
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.03
No. of reflections	1798
No. of parameters	119
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—O11	1.2194 (16)	C12—O12	1.3216 (15)

C2—C3—N3—O31	14.78 (17)	C1—C11—C12—O12	172.54 (11)
C2—C1—C11—C12	117.89 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, y−1/2, −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

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
Grabowski, S. J., Krygowski, T. M., Häfelinger, G. & Ritter, G. (1990). Acta Cryst. C46, 428–430. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland. Google Scholar
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
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. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wardell, 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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ISSN: 2053-2296

Volume 62| Part 11| November 2006| Pages o647-o649

doi:10.1107/S0108270106039205

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

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

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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