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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

4-Nitro­phenyl phenyl ether: sheets built from C—H⋯O and C—H⋯π(arene) hydrogen bonds

aSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland, bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and cInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil
*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 18 January 2005; accepted 20 January 2005; online 28 February 2005)

In the title compound, C12H9NO3, the ether C—O—C angle is 119.65 (10)°. The mol­ecules are linked into sheets by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds, reinforced by an aromatic ππ stacking interaction.

Comment

We report here the molecular and supramolecular structure of the title compound, (I[link]) (Fig. 1[link]), a simple substituted analogue of the low-melting-point parent compound biphenyl ether, Ph2O (m.p. ca 300 K), the structure of which does not appear in the Cambridge Structural Database (January 2005 release; Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). The C—O distance to the substituted ring in (I[link]) is significantly the shorter of the two C—O distances (Table 1[link]), but the mean C—C distances for the two aryl rings are identical within experimental uncertainty. The C—O—C angle is strikingly larger than those typically found in water and simple ethers, which are just below the idealized tetrahedral value. The value of this angle in (I[link]) may be compared with the corresponding C—O—C angle of 127.9 (1)° in Ph3C—O—CPh3 (Glidewell & Liles, 1978[Glidewell, C. & Liles, D. C. (1978). Acta Cryst. B34, 696-698.]). Associated with this large angle is the concerted twist of the aryl rings away from the central C—O—C plane, as indicated by the relevant torsion angles. The dihedral angle between the ring planes is 63.2 (2)°. These geometric features are most readily ascribed to the avoidance of the mutual repulsion between the ortho H atoms bonded to atoms C2 and C16 (Fig. 1[link]).

[Scheme 1]

The mol­ecules of (I[link]) are linked into sheets by a combination of one C—H⋯O hydrogen bond and one C—H⋯π(arene) hydrogen bond, and these sheets are reinforced by an aromatic ππ stacking interaction. Aryl atom C6 in the mol­ecule at (x, y, z) acts as hydrogen-bond donor to nitro atom O42 in the mol­ecule at (1 − x, y − [{1\over 2}], [{1\over 2}] − z), so producing a C(6) (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) chain running parallel to the [010] direction and generated by the 21 screw axis along ([{1\over 2}], y, [{1\over 4}]) (Fig. 2[link]). A similar chain, antiparallel to the first and related to it by inversion, is generated by the 21 screw axis along ([{1\over 2}], −y[{3\over 4}]), and these chains are linked by the C—H⋯π(arene) hydrogen bond.

Aryl atom C2 in the mol­ecule at (x, y, z), which forms part of the chain along ([{1\over 2}], y, [{1\over 4}]), acts as hydrogen-bond donor to the unsubstituted C11–C16 ring in the mol­ecule at (x, [{1\over 2}]y, [{1\over 2}] + z), which lies in the chain along ([{1\over 2}], −y, [{3\over 4}]). In this manner, a second chain motif is produced, running parallel to the [001] direction and generated by the c-glide plane at y = [{1\over 4}] (Fig. 3[link]). The combination of the [010] and [001] chains generates a (100) chain in the form of a (4,4)-net (Batten & Robson, 1998[Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460-1494.]) built from a single type of ring (Fig. 4[link]). Just one sheet of this type passes through each unit cell.

A single aromatic ππ stacking interaction reinforces the sheet. The C1–C6 rings in the mol­ecules at (x, y, z) and (1 − x, 1 − y, 1 − z) are strictly parallel and these mol­ecules lie in the same sheet. The interplanar spacing between these mol­ecules is 3.296 (2) Å and the ring–centroid separation is 3.695 (2) Å, corresponding to a centroid offset of 1.670 (2) Å (Fig. 5[link]). There are no direction-specific interactions between adjacent (100) sheets.

[Figure 1]
Figure 1
The mol­ecule of (I[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 (I[link]), showing the formation of a hydrogen-bonded chain along [010]. Atoms marked with an asterisk (*) or hash (#) are at the symmetry positions (1 − x, y − [{1\over 2}], [{1\over 2}] − z) and (1 − x, [{1\over 2}] + y, [{1\over 2}] − z), respectively.
[Figure 3]
Figure 3
Part of the crystal structure of (I[link]), showing the formation of a hydrogen-bonded chain along [001]. Atoms marked with an asterisk (*), hash (#) or dollar sign ($) are at the symmetry positions (x, [{1\over 2}] − y, [{1\over 2}] + z), (x, y, 1 + z) and (x, [{1\over 2}] − y, z − [{1\over 2}]), respectively.
[Figure 4]
Figure 4
A stereoview of part of the crystal structure of (I[link]), showing the formation of the (100) sheet.
[Figure 5]
Figure 5
Part of the crystal structure of (I[link]), showing the ππ stacking interaction. For the sake of clarity, H atoms have been omitted. The atom marked with an asterisk (*) is at the symmetry position (1 − x, 1 − y, 1 − z).

Experimental

A sample of the title compound was obtained from Aldrich. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in ethanol.

Crystal data
  • C12H9NO3

  • Mr = 215.20

  • Monoclinic, P 21 /c

  • a = 10.3300 (5) Å

  • b = 12.2408 (4) Å

  • c = 7.9804 (4) Å

  • β = 96.215 (2)°

  • V = 1003.17 (8) Å3

  • Z = 4

  • Dx = 1.425 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 2285 reflections

  • θ = 3.1–27.5°

  • μ = 0.10 mm−1

  • T = 120 (2) K

  • Shard, colourless

  • 0.34 × 0.18 × 0.09 mm

Data collection
  • 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 = 0.955, Tmax = 0.991

  • 11 250 measured reflections

  • 2285 independent reflections

  • 1644 reflections with I > 2σ(I)

  • Rint = 0.045

  • θmax = 27.5°

  • h = −13 → 13

  • k = −15 → 15

  • l = −10 → 9

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.113

  • S = 1.04

  • 2285 reflections

  • 146 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0619P)2 + 0.0313P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.29 e Å−3

  • Extinction correction: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.])

  • Extinction coefficient: 0.018 (3)

Table 1
Selected geometric parameters (Å, °)

O1—C1 1.3783 (15)
O1—C11 1.3955 (15)
C1—O1—C11 119.65 (10)
C2—C1—O1—C11 26.75 (19)
C1—O1—C11—C16 47.64 (18)

Table 2
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O42i 0.95 2.54 3.4033 (17) 152
C2—H2⋯Cgii 0.95 2.71 3.428 (2) 134
Symmetry codes: (i) [1-x, y-{\script{1\over 2}}, {\script{1\over 2}}-z]; (ii) [x, {\script{1\over 2}}-y, z+{\script{1\over 2}}].

The space group P21/c was uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.95 Å and with Uiso(H) = 1.2Ueq(C).

Data collection: COLLECT (Hooft, 1999[Hooft, R. W. W. (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 for Windows (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 report here the molecular and supramolecular structure of the title compound, (I), (Fig. 1), a simple substituted analogue of the low-melting-point parent compound biphenyl ether, Ph2O (m.p. ca 300 K), the structure of which does not appear in the January 2005 release of the Cambridge Structural Database (Allen, 2002). The C—O distance to the substituted ring in (I) is significantly the shorter of the two C—O distances (Table 1), but the mean C—C distances for the two aryl rings are identical within experimental uncertainty. The C—O—C angle is strikingly larger than those typically found in water and simple ethers, which are just below the idealized tetrahedral value. The value of this angle in (I) may be compared with the corresponding C—O—C angle of 127.9 (1)° in Ph3C—O—CPh3 (Glidewell & Liles, 1978). Associated with this large angle is the concerted twist of the aryl rings away from the central C—O—C plane, as indicated by the relevant torsional angles. The dihedral angle between the ring planes is 63.2 (2)°. These geometric features are most readily ascribed to the avoidance of the mutual repulsion between the ortho H atoms bonded to C2 and C16 (Fig. 1).

The molecules of (I) are linked into sheets by a combination of one C—H···O hydrogen bond and one C—H···π(arene) hydrogen bond, and these sheets are reinforced by an aromatic ππ stacking interaction. Aryl atom C6 in the molecule at (x, y, z) acts as hydrogen-bond donor to nitro atom O42 in the molecule at (1 − x, y − 1/2, 1/2 − z), so producing a C(6) (Bernstein et al., 1995) chain running parallel to the [010] direction and generated by the 21 screw axis along (1/2, y, 1/4) (Fig. 2). A similar chain, antiparallel to the first and related to it by inversion, is generated by the 21 screw axis along (1/2, −y, 3/4), and these chains are linked by the C—H···π(arene) hydrogen bond.

Aryl atom C2 in the molecule at (x, y, z), which forms part of the chain along (1/2, y, 1/4), acts as hydrogen-bond donor to the unsubstituted C11–C16 ring in the molecule at (x, 1/2 − y, 1/2 + z), which lies in the chain along (1/2, −y, 3/4). In this manner, a second chain motif is produced, running parallel to the [001] direction and generated by the c-glide plane at y = 1/4 (Fig. 3). The combination of the [010] and [001] chains generates a (100) chain in the form of a (4,4) net (Batten & Robson, 1998) built from a single type of ring (Fig. 4). Just one sheet of this type passes through each unit cell.

A single aromatic ππ stacking interaction reinforces the sheet. The C1–C6 rings in the molecules at (x, y, z) and (1 − x, 1 − y, 1 − z) are strictly parallel and these molecules lie in the same sheet. The interplanar spacing between these molecules is 3.296 (2) Å and the ring–centroid separation is 3.695 (2) Å, corresponding to a centroid offset of 1.670 (2) Å (Fig. 5). There are no direction-specific interactions between adjacent (100) sheets.

Experimental top

A sample of the title compound was obtained from Aldrich. Crystals of (I) suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in ethanol.

Refinement top

The space group P21/c was uniquely assigned from the systematic absences. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.95 Å and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: COLLECT (Hooft, 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. The molecule of (I), 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(I), showing the formation of a hydrogen-bonded chain along [010]. The atoms marked with an asterisk (*) or hash (#) are at the symmetry positions (1 − x, y − 1/2, 1/2 − z) and (1 − x, 1/2 + y, 1/2 − z), respectively.
[Figure 3] Fig. 3. Part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain along [001]. The atoms marked with an asterisk (*), hash (#) or dollar sign ($) are at the symmetry positions (x, 1/2 − y, 1/2 + z), (x, y, 1 + z) and (x, 1/2 − y, z − 1/2), respectively.
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of (I), showing the formation of the (100) sheet.
[Figure 5] Fig. 5. Part of the crystal structure of (I), showing the ππ stacking interaction. For the sake of clarity, H atoms have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
4-Nitrophenyl phenyl ether top
Crystal data top
C12H9NO3F(000) = 448
Mr = 215.20Dx = 1.425 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2285 reflections
a = 10.3300 (5) Åθ = 3.1–27.5°
b = 12.2408 (4) ŵ = 0.10 mm1
c = 7.9804 (4) ÅT = 120 K
β = 96.215 (2)°Shard, colourless
V = 1003.17 (8) Å30.34 × 0.18 × 0.09 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
2285 independent reflections
Graphite monochromator1644 reflections with I > 2σ(I)
Detector resolution: 9.091 pixels mm-1Rint = 0.045
ϕ and ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1313
Tmin = 0.955, Tmax = 0.991k = 1515
11250 measured reflectionsl = 109
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0619P)2 + 0.0313P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2285 reflectionsΔρmax = 0.22 e Å3
146 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (3)
Crystal data top
C12H9NO3V = 1003.17 (8) Å3
Mr = 215.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.3300 (5) ŵ = 0.10 mm1
b = 12.2408 (4) ÅT = 120 K
c = 7.9804 (4) Å0.34 × 0.18 × 0.09 mm
β = 96.215 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
2285 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
1644 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.991Rint = 0.045
11250 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.04Δρmax = 0.22 e Å3
2285 reflectionsΔρmin = 0.29 e Å3
146 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.36142 (9)0.31179 (7)0.32222 (13)0.0236 (3)
O410.22322 (10)0.78372 (8)0.54552 (14)0.0310 (3)
O420.38921 (10)0.81782 (8)0.41061 (15)0.0325 (3)
N40.31209 (11)0.75386 (9)0.46511 (16)0.0224 (3)
C10.34314 (12)0.42031 (10)0.35927 (17)0.0193 (3)
C20.25253 (12)0.45470 (11)0.46435 (18)0.0215 (3)
C30.24360 (13)0.56507 (11)0.50037 (18)0.0214 (3)
C40.32547 (12)0.63742 (10)0.43173 (17)0.0195 (3)
C50.41804 (12)0.60360 (11)0.32985 (18)0.0210 (3)
C60.42682 (12)0.49404 (11)0.29330 (18)0.0204 (3)
C110.25903 (12)0.23800 (10)0.32812 (18)0.0200 (3)
C120.28895 (14)0.13855 (11)0.40378 (17)0.0224 (3)
C130.19265 (14)0.05949 (11)0.40325 (18)0.0265 (4)
C140.06804 (14)0.08090 (12)0.32944 (19)0.0280 (4)
C150.03923 (14)0.18169 (12)0.25384 (19)0.0262 (4)
C160.13495 (13)0.26051 (11)0.25177 (19)0.0234 (3)
H20.19740.40340.51090.026*
H30.18190.59050.57140.026*
H50.47450.65500.28590.025*
H60.48960.46900.22350.024*
H120.37450.12430.45560.027*
H130.21250.00960.45380.032*
H140.00210.02690.33030.034*
H150.04660.19640.20340.031*
H160.11590.32900.19880.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0204 (5)0.0176 (5)0.0334 (6)0.0013 (4)0.0060 (4)0.0014 (4)
O410.0293 (5)0.0258 (6)0.0397 (7)0.0011 (4)0.0114 (5)0.0047 (5)
O420.0318 (6)0.0213 (5)0.0458 (7)0.0067 (4)0.0104 (5)0.0031 (5)
N40.0210 (6)0.0210 (6)0.0251 (7)0.0015 (5)0.0015 (5)0.0014 (5)
C10.0191 (6)0.0178 (7)0.0204 (8)0.0005 (5)0.0009 (6)0.0003 (5)
C20.0215 (7)0.0208 (7)0.0227 (8)0.0025 (5)0.0041 (6)0.0032 (6)
C30.0193 (7)0.0246 (7)0.0204 (8)0.0018 (5)0.0033 (6)0.0017 (6)
C40.0200 (7)0.0170 (7)0.0206 (8)0.0011 (5)0.0015 (6)0.0003 (6)
C50.0187 (6)0.0230 (7)0.0209 (8)0.0030 (6)0.0000 (6)0.0042 (6)
C60.0172 (6)0.0237 (7)0.0204 (8)0.0003 (5)0.0028 (6)0.0003 (6)
C110.0208 (7)0.0186 (7)0.0214 (8)0.0022 (5)0.0063 (6)0.0027 (5)
C120.0238 (7)0.0231 (7)0.0204 (8)0.0039 (6)0.0035 (6)0.0005 (6)
C130.0383 (9)0.0185 (7)0.0238 (9)0.0009 (6)0.0086 (7)0.0007 (6)
C140.0300 (8)0.0251 (8)0.0303 (9)0.0081 (6)0.0104 (7)0.0064 (6)
C150.0215 (7)0.0288 (8)0.0283 (9)0.0020 (6)0.0034 (6)0.0038 (6)
C160.0250 (7)0.0225 (7)0.0231 (8)0.0024 (6)0.0042 (6)0.0003 (6)
Geometric parameters (Å, º) top
O1—C11.3783 (15)N4—O411.2311 (15)
C1—C21.3880 (19)O1—C111.3955 (15)
C1—C61.3919 (19)C11—C121.3790 (18)
C2—C31.3864 (19)C11—C161.3860 (19)
C2—H20.95C12—C131.3875 (19)
C3—C41.3784 (19)C12—H120.95
C3—H30.95C13—C141.382 (2)
C4—C51.3839 (19)C13—H130.95
C4—N41.4593 (17)C14—C151.391 (2)
C5—C61.3775 (19)C14—H140.95
C5—H50.95C15—C161.3829 (19)
C6—H60.95C15—H150.95
N4—O421.2296 (15)C16—H160.95
O1—C1—C2122.61 (12)O41—N4—C4118.41 (11)
O1—C1—C6116.02 (12)C1—O1—C11119.65 (10)
C2—C1—C6121.26 (12)C12—C11—C16121.39 (13)
C3—C2—C1119.02 (12)C12—C11—O1116.83 (12)
C3—C2—H2120.5C16—C11—O1121.65 (12)
C1—C2—H2120.5C11—C12—C13119.19 (13)
C4—C3—C2119.10 (13)C11—C12—H12120.4
C4—C3—H3120.4C13—C12—H12120.4
C2—C3—H3120.4C14—C13—C12120.24 (13)
C3—C4—C5122.27 (12)C14—C13—H13119.9
C3—C4—N4118.73 (12)C12—C13—H13119.9
C5—C4—N4118.98 (12)C13—C14—C15119.92 (13)
C6—C5—C4118.76 (12)C13—C14—H14120.0
C6—C5—H5120.6C15—C14—H14120.0
C4—C5—H5120.6C16—C15—C14120.28 (13)
C5—C6—C1119.56 (13)C16—C15—H15119.9
C5—C6—H6120.2C14—C15—H15119.9
C1—C6—H6120.2C15—C16—C11118.97 (13)
O42—N4—O41122.93 (11)C15—C16—H16120.5
O42—N4—C4118.65 (11)C11—C16—H16120.5
O1—C1—C2—C3177.57 (11)C5—C4—N4—O41174.73 (12)
C6—C1—C2—C31.6 (2)C2—C1—O1—C1126.75 (19)
C1—C2—C3—C40.4 (2)C6—C1—O1—C11157.09 (12)
C2—C3—C4—C51.0 (2)C1—O1—C11—C12136.55 (13)
C2—C3—C4—N4177.71 (12)C1—O1—C11—C1647.64 (18)
C3—C4—C5—C61.3 (2)C16—C11—C12—C130.0 (2)
N4—C4—C5—C6177.47 (11)O1—C11—C12—C13175.80 (12)
C4—C5—C6—C10.1 (2)C11—C12—C13—C140.8 (2)
O1—C1—C6—C5177.58 (12)C12—C13—C14—C150.6 (2)
C2—C1—C6—C51.4 (2)C13—C14—C15—C160.2 (2)
C3—C4—N4—O42176.54 (12)C14—C15—C16—C110.9 (2)
C5—C4—N4—O424.66 (19)C12—C11—C16—C150.8 (2)
C3—C4—N4—O414.06 (19)O1—C11—C16—C15176.43 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O42i0.952.543.4033 (17)152
C2—H2···Cgii0.952.713.428 (2)134
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC12H9NO3
Mr215.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)10.3300 (5), 12.2408 (4), 7.9804 (4)
β (°) 96.215 (2)
V3)1003.17 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.34 × 0.18 × 0.09
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.955, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
11250, 2285, 1644
Rint0.045
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.113, 1.04
No. of reflections2285
No. of parameters146
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.29

Computer programs: COLLECT (Hooft, 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
O1—C11.3783 (15)O1—C111.3955 (15)
C1—O1—C11119.65 (10)
C2—C1—O1—C1126.75 (19)C1—O1—C11—C1647.64 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O42i0.952.543.4033 (17)152
C2—H2···Cgii0.952.713.428 (2)134
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1/2, z+1/2.
 

Acknowledgements

The X-ray data were collected at the EPSRC X-ray Crystal­lographic Service, University of Southampton, England; the authors thank the staff for all their help and advice. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work. JLW thanks CNPq and FAPERJ for financial support.

References

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First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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