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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

Chains of edge-fused hydrogen-bonded R33(12) rings in N-phenyl-4-nitro­phthalimide

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 3 February 2005; accepted 7 February 2005; online 11 March 2005)

Mol­ecules of the title compound [systematic name: 5-nitro-1H-isoindole-1,3(2H)-dione], C14H8N2O4, adopt a conformation in the solid state which renders them chiral, and they are linked by three distinct types of direction-specific inter­molecular inter­action. The mol­ecules are linked by two C—H⋯O hydrogen bonds [H⋯O = 2.50 and 2.52 Å, C⋯O = 3.118 (7) and 3.294 (7) Å, and C—H⋯O = 123 and 139°] into chains of edge-fused [R_{3}^{3}](12) rings, which are themselves weakly linked into sheets by a combination of an aromatic ππ stacking inter­action and a sheared-parallel carbon­yl–carbonyl inter­action.

Comment

As part of a study of the supramolecular arrangements in N-arylnitro­phthalimides, the title compound, (I)[link] (Fig. 1[link]), has been prepared and its structure determined. The small and rather simple mol­ecules of (I)[link] are involved in three distinct types of direction-specific inter­molecular inter­action.

[Scheme 1]

The dihedral angle in (I)[link] between the C11–C16 aryl ring and the heterocyclic ring is 36.2 (2)°. Associated with this inter-ring twist are two fairly short intra­molecular C—H⋯O contacts (Table 1[link]), which are probably weakly attractive, in view of the likely positive polarization of the aryl H atoms and the negative polarization of the carbonyl O atoms. In addition, the nitro group is not quite coplanar with the adjacent C3–C8 aromatic ring; the dihedral angle between this ring and the C5/N5/O51/O52 plane is 6.4 (3)°. Accordingly, the mol­ecules have no internal symmetry and are chiral. Thus, in space group P212121, only one enantiomorph will be present in each crystal, providing that inversion twinning is absent. The bond lengths and angles present no unusual features.

Mol­ecules of (I)[link] are linked into chains by the co-operative action of two C—H⋯O hydrogen bonds, each individually of only modest strength and each having a nitro O atom as acceptor, as opposed to the more usual carbonyl O atom. Aryl atom C7 in the mol­ecule at (x, y, z) acts as hydrogen-bond donor to nitro atom O51 in the mol­ecule at (x, −1 + y, z), so generating by translation 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 (Fig. 2[link]). There are four chains of this type passing through each unit cell and they are linked in pairs by the second hydrogen bond. Aryl atom C6 at (x, y, z) acts as donor towards nitro atom O52 in the mol­ecule at (1 − x, −[{1\over 2}] + y, [{3\over 2}] − z), so forming a second chain running parallel to [010], this time of C(5) type generated by the 21 screw axis along ([{1\over 2}], y, [{3\over 4}]). The combination of these two simple chain motifs generates a chain of edge-fused [R_{3}^{3}](12) rings (Fig. 2[link]).

The chains of rings are weakly linked into sheets by a combination of an aromatic ππ stacking inter­action and a dipolar inter­action between carbonyl groups. The C3–C8 and C11–C16 rings in the mol­ecules at (x, y, z) and (2 − x, [{1\over 2}] + y, [{3\over 2}] − z), respectively, are components of the chains of rings generated by the 21 screw axes along ([{1\over 2}], y, [{3\over 4}]) and ([{3\over 2}], y, [{3\over 4}]). These two rings make a dihedral angle of 12.7 (2)°, but their ring-centroid separation of 3.770 (3) Å and inter­planar separation of ca 3.6 Å suggest a structurally significant inter­action, the effect of which is to link [010] chains into (001) sheets. This linking of [010] chains is reinforced by an attractive dipolar inter­action involving the two carbonyl groups. The C1—O1 carbon­yl group in the mol­ecule at (x, y, z), which forms part of the chain along ([{1\over 2}], y, [{3\over 4}]), forms a type III sheared-parallel inter­action (Allen et al., 1998[Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320-329.]) with the C2—O2 carbonyl group in the mol­ecule at (2 − x, −[{1\over 2}] + y, [{3\over 2}] − z), part of the chain along ([{3\over 2}], y, [{3\over 4}]). The O1⋯C2i distance is 2.957 (5) Å, and the C1—O1⋯C2i and O1⋯C2i—O2i angles are 118.5 (3) and 107.0 (2)°, respectively [symmetry code: (i) 2 − x, −[{1\over 2}] + y, [{3\over 2}] − z]. It may be noted here that, although the carbonyl O atoms participate in both of the short intra­molecular contacts and in the inter­molecular dipolar inter­actions, they play no part at all in the inter­molecular hydrogen bonding.

Two (010) sheets pass through each unit cell, generated by 21 screw axes at z = [{1\over 4}] and z = [{3\over 4}], but there are no direction-specific inter­actions between adjacent sheets.

It is of interest to compare briefly the supramolecular structure of (I)[link] with those of isomeric compounds having the nitro substituent in the N-phenyl ring. In N-(2-nitro­phenyl)phthalimide (Voliotis et al., 1984[Voliotis, S., Arrieta, J. M. & Germain, G. (1984). Acta Cryst. C40, 1946-1948.]), pairs of mol­ecules are linked by a single C—H⋯O hydrogen bond into R22(14) dimers, which are themselves linked into π-stacked chains, while in N-(3-nitro­phenyl)phthalimide (Glidewell et al., 2004[Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2004). Acta Cryst. C60, o24-o27.]), the mol­ecules are linked into a three-dimensional framework utilizing four independent C—H⋯O hydrogen bonds.

[Figure 1]
Figure 1
The mol­ecule of (I)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2]
Figure 2
Part of the crystal structure of (I)[link], showing the formation of a chain of [R_{3}^{3}](12) rings along [010]. Atoms marked with an asterisk (*), hash (#), dollar sign ($) or ampersand (&) are at the symmetry positions (x, −1 + y, z), (x, 1 + y, z), (1 − x, −[{1\over 2}] + y, [{3\over 2}] − z) and (1 − x, [{1\over 2}] + y, [{3\over 2}] − z), respectively.

Experimental

A well ground mixture of PhNH2 (0.19 g, 2 mmol) and 4-nitro­phthalic anhydride (0.38 g, 2 mmol) was carefully heated at 473 K until effervescence (water evolution) ceased. To the cooled solid residue was added chloro­form (10 ml) and activated charcoal. The resulting mixture was heated to reflux, filtered, and the filtrate evaporated. The residue was recrystallized from ethanol to provide compound (I)[link].

Crystal data
  • C14H8N2O4

  • Mr = 268.22

  • Orthorhombic, P 21 21 21

  • a = 11.9288 (6) Å

  • b = 7.0604 (2) Å

  • c = 13.8337 (7) Å

  • V = 1165.10 (9) Å3

  • Z = 4

  • Dx = 1.529 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 1554 reflections

  • θ = 2.9–27.6°

  • μ = 0.12 mm−1

  • T = 120 (2) K

  • Needle, yellow

  • 0.12 × 0.04 × 0.03 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 = 0.963, Tmax = 0.997

  • 13 798 measured reflections

  • 1554 independent reflections

  • 1318 reflections with I > 2σ(I)

  • Rint = 0.070

  • θmax = 27.6°

  • h = −15 → 13

  • k = −9 → 9

  • l = −17 → 17

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.171

  • S = 1.09

  • 1554 reflections

  • 181 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.0641P)2 + 1.6397P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O52i 0.95 2.52 3.294 (6) 139
C7—H7⋯O51ii 0.95 2.50 3.118 (7) 123
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x, y-1, z.

All H atoms were located from difference maps and then treated as riding atoms [C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C)]. In the absence of significant anomalous dispersion, the Flack parameter (Flack, 1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]) was inconclusive (Flack & Bernardinelli, 2000[Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148.]). Hence, the Friedel-equivalent reflections were merged prior to the final refinement and it was not possible to determine the absolute configuration of the mol­ecules in the crystal used for the data collection. However, this configuration has no chemical significance.

Data collection: COLLECT (Hooft, 1999[Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement and data reduction: 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; structure solution: 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.]); structure refinement: 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

As part of a study of the supramolecular arrangements in N-aryl-nitrophthalimides, the title compound, (I) (Fig. 1), has been prepared and its structure determined. The small and rather simple molecules of (I) are involved in three distinct types of direction-specific intermolecular interaction.

The dihedral angle in (I) between the C11–C16 aryl ring and the heterocyclic ring is 36.2 (2)°. Associated with this inter-ring twist are two fairly short intramolecular C—H···O contacts (Table 1), which are probably weakly attractive, in view of the likely positive polarization of the aryl H atoms and the negative polarization of the carbonyl O atoms. In addition, the nitro group is not quite coplanar with the adjacent C3–C8 aromatic ring: the dihedral angle between this ring and the C5/N5/O51/O52 plane is 6.4 (3)°. Accordingly, the molecules have no internal symmetry and they are chiral. Thus, in space group P212121, only one enantiomorph will be present in each crystal, providing that inversion twinning is absent. The bond lengths and angles present no unusual features.

The molecules of (I) are linked into chains by the cooperative action of two C—H···O hydrogen bonds, each individually of only modest strength and each having a nitro O atom as acceptor, as opposed to the more usual carbonyl O atom. Aryl atom C7 in the molecule at (x, y, z) acts as hydrogen-bond donor to nitro atom O51 in the molecule at (x, −1 + y, z), so generating by translation a C(6) (Bernstein et al., 1995) chain running parallel to the [010] direction (Fig. 2). There are four chains of this type passing through each unit cell and they are linked in pairs by the second hydrogen bond. Aryl atom C6 at (x, y, z) acts as donor towards nitro atom O52 in the molecule at (1 − x, −1/2 + y, 3/2 − z), so forming a second chain running parallel to [010], this time of C(5) type generated by the 21 screw axis along (1/2, y, 3/4). The combination of these two simple chain motifs generates a chain of edge-fused R33(12) rings (Fig. 2).

The chains of rings are weakly linked into sheets by a combination of an aromatic ππ stacking interaction and a dipolar interaction between carbonyl groups. The C3–C8 and C11–C16 rings in the molecules at (x, y, z) and (2 − x, 1/2 + y, 3/2 − z), respectively, are components of the chains of rings generated by the 21 screw axes along (1/2, y, 3/4) and (3/2, y, 3/4). These two rings make a dihedral angle of 12.7 (2)°, but their ring-centroid separation of 3.770 (3) Å and interplanar separation of ca 3.6 Å s u ggest a structurally significant interaction, the effect of which is to link [010] chains into (001) sheets. This linking of [010] chains is reinforced by an attractive dipolar interaction involving the two carbonyl groups. The C1—O1 carbonyl group in the molecule at (x, y, z), which forms part of the chain along (1/2, y, 3/4), forms a type III sheared-parallel interaction (Allen et al., 1998) with the C2—O2 carbonyl group in the molecule at (2 − x, −1/2 + y, 3/2 − z), part of the chain along (3/2, y, 3/4). The O1···C2i distance [symmetry code: (i) 2 − x, −1/2 + y, 3/2 − z] is 2.957 (5) Å, and the C1—O1···C2i and O1···C2i—O2i angles are 118.5 (3) and 107.0 (2)°, respectively. It may be noted here that, although the carbonyl O atoms participate in both short intramolecular contacts and in intermolecular dipolar interactions, they play no part at all in the intermolecular hydrogen bonding.

Two (010) sheets pass through each unit cell, generated respectively by 21 screw axes at z = 1/4 and z = 3/4, but there are no direction-specific interactions between adjacent sheets.

It is of interest to compare briefly the supramolecular structure of (I) with those of isomeric compounds having the nitro substituent in the N-phenyl ring. In N-(2-nitrophenyl)phthalimide (Voliotis et al., 1984), pairs of molecules are linked by a single C—H···O hydrogen bond into R22(14) dimers, which are themselves linked into π-stacked chains, while in N-(3-nitrophenyl)phthalimide (Glidewell et al., 2004), the molecules are linked into a three-dimensional framework utilizing four independent C—H···O hydrogen bonds.

Experimental top

A well ground mixture of PhNH2 (0.19 g, 2 mmol) and 4-nitrophthalic anhydride (0.38 g, 2 mmol) was carefully heated at 473 K until effervescence (water evolution) ceased. To the cooled solid residue was added chloroform (10 ml) and activated charcoal. The resulting mixture was heated to reflux, filtered, and the filtrate evaporated. The residue was recrystallized from ethanol to provide compound (I).

Refinement top

The space group P212121 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). In the absence of significant anomalous dispersion, the Flack parameter (Flack, 1983) was inconclusive (Flack & Bernardinelli, 2000). Hence, the Friedel-equivalent reflections were merged prior to the final refinement and it was not possible to determine the absolute configuration of the molecules in the crystal used for the data collection. However, this configuration has no chemical significance.

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.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of a chain of R33(12) ring alongs [010]. Atoms marked with an asterisk (*), hash (#), dollar sign ($) or ampersand (&) are at the symmetry positions (x, −1 + y, z), (x, 1 + y, z), (1 − x, −1/2 + y, 3/2 − z) and (1 − x, 1/2 + y, 3/2 − z), respectively
N-Phenyl-4-nitrophthalimide top
Crystal data top
C14H8N2O4F(000) = 552
Mr = 268.22Dx = 1.529 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1554 reflections
a = 11.9288 (6) Åθ = 2.9–27.6°
b = 7.0604 (2) ŵ = 0.12 mm1
c = 13.8337 (7) ÅT = 120 K
V = 1165.10 (9) Å3Needle, yellow
Z = 40.12 × 0.04 × 0.03 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1554 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1318 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
Detector resolution: 9.091 pixels mm-1θmax = 27.6°, θmin = 2.9°
ϕ and ω scansh = 1513
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 99
Tmin = 0.963, Tmax = 0.997l = 1717
13798 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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0641P)2 + 1.6397P]
where P = (Fo2 + 2Fc2)/3
1554 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C14H8N2O4V = 1165.10 (9) Å3
Mr = 268.22Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.9288 (6) ŵ = 0.12 mm1
b = 7.0604 (2) ÅT = 120 K
c = 13.8337 (7) Å0.12 × 0.04 × 0.03 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1554 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
1318 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.997Rint = 0.070
13798 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.171H-atom parameters constrained
S = 1.09Δρmax = 0.39 e Å3
1554 reflectionsΔρmin = 0.25 e Å3
181 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N11.0377 (3)0.4517 (5)0.6196 (3)0.0282 (8)
C10.9520 (4)0.3459 (7)0.6640 (3)0.0325 (10)
O10.9594 (3)0.1872 (5)0.6951 (2)0.0396 (8)
C21.0001 (4)0.6356 (6)0.5957 (3)0.0319 (10)
O21.0547 (3)0.7551 (5)0.5542 (3)0.0426 (9)
C30.8803 (4)0.6421 (7)0.6261 (3)0.0328 (10)
C40.8037 (4)0.7882 (7)0.6190 (3)0.0340 (10)
C50.6965 (4)0.7423 (7)0.6524 (3)0.0324 (10)
C60.6648 (4)0.5719 (8)0.6898 (4)0.0391 (11)
C70.7442 (4)0.4292 (8)0.6962 (4)0.0393 (11)
C80.8516 (4)0.4702 (7)0.6646 (3)0.0340 (10)
N50.6083 (4)0.8913 (7)0.6463 (3)0.0472 (11)
O510.6387 (3)1.0524 (5)0.6218 (3)0.0533 (10)
O520.5135 (3)0.8489 (6)0.6684 (3)0.0563 (11)
C111.1507 (4)0.3832 (7)0.6066 (3)0.0300 (10)
C121.2394 (4)0.5091 (8)0.6192 (4)0.0395 (11)
C131.3480 (4)0.4436 (9)0.6049 (4)0.0478 (14)
C141.3674 (5)0.2591 (9)0.5812 (4)0.0493 (14)
C151.2784 (5)0.1356 (8)0.5700 (4)0.0498 (15)
C161.1679 (4)0.1969 (7)0.5813 (3)0.0356 (11)
H40.82220.90920.59360.041*
H60.59000.55150.71100.047*
H70.72560.30790.72140.047*
H121.22600.63690.63720.047*
H131.40940.52840.61160.057*
H141.44200.21540.57240.059*
H151.29260.00680.55430.060*
H161.10670.11290.57190.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0293 (18)0.0260 (17)0.0293 (17)0.0050 (16)0.0005 (15)0.0017 (16)
C10.030 (2)0.041 (3)0.026 (2)0.002 (2)0.0032 (18)0.004 (2)
O10.0431 (19)0.0407 (19)0.0349 (17)0.0015 (17)0.0020 (15)0.0117 (15)
C20.040 (2)0.026 (2)0.029 (2)0.003 (2)0.0014 (19)0.0012 (18)
O20.048 (2)0.0315 (16)0.048 (2)0.0004 (17)0.0055 (16)0.0016 (16)
C30.033 (2)0.038 (2)0.027 (2)0.003 (2)0.0023 (18)0.008 (2)
C40.040 (2)0.031 (2)0.031 (2)0.001 (2)0.001 (2)0.002 (2)
C50.030 (2)0.036 (2)0.031 (2)0.006 (2)0.0026 (19)0.005 (2)
C60.032 (2)0.051 (3)0.035 (2)0.008 (2)0.002 (2)0.005 (2)
C70.035 (2)0.048 (3)0.035 (2)0.006 (2)0.004 (2)0.007 (2)
C80.037 (2)0.040 (3)0.025 (2)0.001 (2)0.0059 (19)0.001 (2)
N50.042 (3)0.053 (3)0.046 (3)0.007 (2)0.004 (2)0.004 (2)
O510.055 (2)0.042 (2)0.063 (2)0.0103 (19)0.002 (2)0.006 (2)
O520.0322 (18)0.065 (3)0.072 (3)0.0077 (19)0.0092 (18)0.001 (2)
C110.032 (2)0.036 (2)0.0213 (19)0.006 (2)0.0038 (17)0.0005 (19)
C120.035 (2)0.047 (3)0.037 (2)0.002 (2)0.002 (2)0.001 (2)
C130.038 (3)0.064 (4)0.041 (3)0.005 (3)0.001 (2)0.008 (3)
C140.036 (2)0.074 (4)0.038 (3)0.015 (3)0.006 (2)0.015 (3)
C150.068 (4)0.051 (3)0.030 (2)0.029 (3)0.011 (2)0.008 (3)
C160.047 (3)0.035 (2)0.025 (2)0.008 (2)0.005 (2)0.0023 (19)
Geometric parameters (Å, º) top
N1—C11.407 (6)C7—C81.385 (7)
N1—C21.413 (6)C7—H70.95
N1—C111.443 (6)N5—O521.209 (6)
C1—O11.204 (6)N5—O511.242 (6)
C1—C81.484 (6)C11—C161.377 (7)
C2—O21.211 (5)C11—C121.393 (7)
C2—C31.490 (6)C12—C131.389 (7)
C3—C81.369 (7)C12—H120.95
C3—C41.381 (6)C13—C141.363 (9)
C4—C51.398 (6)C13—H130.95
C4—H40.95C14—C151.383 (9)
C5—C61.363 (7)C14—H140.95
C5—N51.490 (6)C15—C161.396 (7)
C6—C71.386 (7)C15—H150.95
C6—H60.95C16—H160.95
C1—N1—C2111.0 (4)C3—C8—C7122.6 (5)
C1—N1—C11123.8 (4)C3—C8—C1108.7 (4)
C2—N1—C11125.1 (4)C7—C8—C1128.7 (5)
O1—C1—N1126.7 (4)O52—N5—O51124.7 (5)
O1—C1—C8127.4 (5)O52—N5—C5118.2 (5)
N1—C1—C8106.0 (4)O51—N5—C5117.1 (4)
O2—C2—N1125.4 (4)C16—C11—C12121.8 (5)
O2—C2—C3128.9 (4)C16—C11—N1119.4 (4)
N1—C2—C3105.5 (4)C12—C11—N1118.7 (4)
C8—C3—C4121.6 (4)C13—C12—C11118.6 (5)
C8—C3—C2108.8 (4)C13—C12—H12120.7
C4—C3—C2129.6 (5)C11—C12—H12120.7
C3—C4—C5114.1 (4)C14—C13—C12120.7 (6)
C3—C4—H4122.9C14—C13—H13119.7
C5—C4—H4122.9C12—C13—H13119.7
C6—C5—C4125.7 (4)C13—C14—C15120.0 (5)
C6—C5—N5116.6 (4)C13—C14—H14120.0
C4—C5—N5117.6 (4)C15—C14—H14120.0
C5—C6—C7118.5 (4)C14—C15—C16121.1 (5)
C5—C6—H6120.8C14—C15—H15119.4
C7—C6—H6120.8C16—C15—H15119.4
C8—C7—C6117.4 (5)C11—C16—C15117.8 (5)
C8—C7—H7121.3C11—C16—H16121.1
C6—C7—H7121.3C15—C16—H16121.1
C2—N1—C1—O1177.5 (4)C6—C7—C8—C31.5 (7)
C11—N1—C1—O11.2 (7)C6—C7—C8—C1179.5 (4)
C2—N1—C1—C82.2 (5)O1—C1—C8—C3177.3 (5)
C11—N1—C1—C8178.5 (4)N1—C1—C8—C32.4 (5)
C1—N1—C2—O2177.6 (4)O1—C1—C8—C73.6 (8)
C11—N1—C2—O26.2 (7)N1—C1—C8—C7176.7 (5)
C1—N1—C2—C31.2 (5)C6—C5—N5—O525.0 (7)
C11—N1—C2—C3177.5 (4)C4—C5—N5—O52174.7 (5)
O2—C2—C3—C8175.8 (5)C6—C5—N5—O51172.8 (5)
N1—C2—C3—C80.3 (5)C4—C5—N5—O517.5 (7)
O2—C2—C3—C43.6 (8)C1—N1—C11—C1639.3 (6)
N1—C2—C3—C4179.7 (5)C2—N1—C11—C16145.0 (4)
C8—C3—C4—C51.2 (7)C1—N1—C11—C12141.3 (4)
C2—C3—C4—C5178.1 (4)C2—N1—C11—C1234.5 (6)
C3—C4—C5—C60.2 (7)C16—C11—C12—C130.6 (7)
C3—C4—C5—N5179.4 (4)N1—C11—C12—C13178.8 (4)
C4—C5—C6—C70.1 (8)C11—C12—C13—C141.6 (8)
N5—C5—C6—C7179.7 (4)C12—C13—C14—C150.9 (8)
C5—C6—C7—C80.5 (7)C13—C14—C15—C160.8 (8)
C4—C3—C8—C72.0 (7)C12—C11—C16—C151.0 (7)
C2—C3—C8—C7177.5 (4)N1—C11—C16—C15179.6 (4)
C4—C3—C8—C1178.9 (4)C14—C15—C16—C111.7 (7)
C2—C3—C8—C11.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O52i0.952.523.294 (6)139
C7—H7···O51ii0.952.503.118 (7)123
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC14H8N2O4
Mr268.22
Crystal system, space groupOrthorhombic, P212121
Temperature (K)120
a, b, c (Å)11.9288 (6), 7.0604 (2), 13.8337 (7)
V3)1165.10 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.12 × 0.04 × 0.03
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.963, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
13798, 1554, 1318
Rint0.070
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.171, 1.09
No. of reflections1554
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.25

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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O52i0.952.523.294 (6)139
C7—H7···O51ii0.952.503.118 (7)123
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x, y1, z.
 

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

First citationAllen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationBernstein, 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
First citationFerguson, G. (1999). PRPKAPPA. University of Guelph, Canada.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationFlack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143–1148.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationGlidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2004). Acta Cryst. C60, o24–o27.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationHooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationMcArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.  Google Scholar
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 citationVoliotis, S., Arrieta, J. M. & Germain, G. (1984). Acta Cryst. C40, 1946–1948.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar

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