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

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

doi:10.1107/S0108270105004245

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 61| Part 4| April 2005| Pages o209-o210

doi:10.1107/S0108270105004245

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

Christopher Glidewell,^a ^* John N. Low,^b Janet M. S. Skakle ^b and James L. Wardell ^c

^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 π–π 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) (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 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) 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 ) 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, − $[{1\over 2}]$ + 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).

The chains of rings are weakly linked into sheets by a combination of an aromatic π–π 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 ) 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) 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.

Figure 1
The molecule of (I)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
Part of the crystal structure of (I)

, 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).

Crystal data

C₁₄H₈N₂O₄
M_r = 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
D_x = 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 )T_min = 0.963, T_max = 0.997
13 798 measured reflections
1554 independent reflections
1318 reflections with I > 2σ(I)
R_int = 0.070
θ_max = 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(F_o²) + (0.0641P)² + 1.6397P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 U_iso(H) = 1.2U_eq(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.

Data collection: COLLECT (Hooft, 1999 ); cell refinement and data reduction: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; structure solution: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); structure refinement: 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, I. DOI: 10.1107/S0108270105004245/sk1814sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270105004245/sk1814Isup2.hkl

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 π–π 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

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

	Fig. 1. The molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	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

C₁₄H₈N₂O₄	F(000) = 552
M_r = 268.22	D_x = 1.529 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1554 reflections
a = 11.9288 (6) Å	θ = 2.9–27.6°
b = 7.0604 (2) Å	µ = 0.12 mm⁻¹
c = 13.8337 (7) Å	T = 120 K
V = 1165.10 (9) Å³	Needle, yellow
Z = 4	0.12 × 0.04 × 0.03 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	1554 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1318 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.6°, θ_min = 2.9°
ϕ and ω scans	h = −15→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −9→9
T_min = 0.963, T_max = 0.997	l = −17→17
13798 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0641P)² + 1.6397P] where P = (F_o² + 2F_c²)/3
1554 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₄H₈N₂O₄	V = 1165.10 (9) Å³
M_r = 268.22	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.9288 (6) Å	µ = 0.12 mm⁻¹
b = 7.0604 (2) Å	T = 120 K
c = 13.8337 (7) Å	0.12 × 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)
T_min = 0.963, T_max = 0.997	R_int = 0.070
13798 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 1.09	Δρ_max = 0.39 e Å⁻³
1554 reflections	Δρ_min = −0.25 e Å⁻³
181 parameters

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

	x	y	z	U_iso*/U_eq
N1	1.0377 (3)	0.4517 (5)	0.6196 (3)	0.0282 (8)
C1	0.9520 (4)	0.3459 (7)	0.6640 (3)	0.0325 (10)
O1	0.9594 (3)	0.1872 (5)	0.6951 (2)	0.0396 (8)
C2	1.0001 (4)	0.6356 (6)	0.5957 (3)	0.0319 (10)
O2	1.0547 (3)	0.7551 (5)	0.5542 (3)	0.0426 (9)
C3	0.8803 (4)	0.6421 (7)	0.6261 (3)	0.0328 (10)
C4	0.8037 (4)	0.7882 (7)	0.6190 (3)	0.0340 (10)
C5	0.6965 (4)	0.7423 (7)	0.6524 (3)	0.0324 (10)
C6	0.6648 (4)	0.5719 (8)	0.6898 (4)	0.0391 (11)
C7	0.7442 (4)	0.4292 (8)	0.6962 (4)	0.0393 (11)
C8	0.8516 (4)	0.4702 (7)	0.6646 (3)	0.0340 (10)
N5	0.6083 (4)	0.8913 (7)	0.6463 (3)	0.0472 (11)
O51	0.6387 (3)	1.0524 (5)	0.6218 (3)	0.0533 (10)
O52	0.5135 (3)	0.8489 (6)	0.6684 (3)	0.0563 (11)
C11	1.1507 (4)	0.3832 (7)	0.6066 (3)	0.0300 (10)
C12	1.2394 (4)	0.5091 (8)	0.6192 (4)	0.0395 (11)
C13	1.3480 (4)	0.4436 (9)	0.6049 (4)	0.0478 (14)
C14	1.3674 (5)	0.2591 (9)	0.5812 (4)	0.0493 (14)
C15	1.2784 (5)	0.1356 (8)	0.5700 (4)	0.0498 (15)
C16	1.1679 (4)	0.1969 (7)	0.5813 (3)	0.0356 (11)
H4	0.8222	0.9092	0.5936	0.041*
H6	0.5900	0.5515	0.7110	0.047*
H7	0.7256	0.3079	0.7214	0.047*
H12	1.2260	0.6369	0.6372	0.047*
H13	1.4094	0.5284	0.6116	0.057*
H14	1.4420	0.2154	0.5724	0.059*
H15	1.2926	0.0068	0.5543	0.060*
H16	1.1067	0.1129	0.5719	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0293 (18)	0.0260 (17)	0.0293 (17)	0.0050 (16)	−0.0005 (15)	−0.0017 (16)
C1	0.030 (2)	0.041 (3)	0.026 (2)	0.002 (2)	−0.0032 (18)	−0.004 (2)
O1	0.0431 (19)	0.0407 (19)	0.0349 (17)	−0.0015 (17)	0.0020 (15)	0.0117 (15)
C2	0.040 (2)	0.026 (2)	0.029 (2)	0.003 (2)	−0.0014 (19)	−0.0012 (18)
O2	0.048 (2)	0.0315 (16)	0.048 (2)	−0.0004 (17)	0.0055 (16)	0.0016 (16)
C3	0.033 (2)	0.038 (2)	0.027 (2)	0.003 (2)	−0.0023 (18)	−0.008 (2)
C4	0.040 (2)	0.031 (2)	0.031 (2)	0.001 (2)	−0.001 (2)	−0.002 (2)
C5	0.030 (2)	0.036 (2)	0.031 (2)	0.006 (2)	−0.0026 (19)	−0.005 (2)
C6	0.032 (2)	0.051 (3)	0.035 (2)	−0.008 (2)	−0.002 (2)	0.005 (2)
C7	0.035 (2)	0.048 (3)	0.035 (2)	−0.006 (2)	−0.004 (2)	0.007 (2)
C8	0.037 (2)	0.040 (3)	0.025 (2)	0.001 (2)	−0.0059 (19)	0.001 (2)
N5	0.042 (3)	0.053 (3)	0.046 (3)	0.007 (2)	−0.004 (2)	−0.004 (2)
O51	0.055 (2)	0.042 (2)	0.063 (2)	0.0103 (19)	0.002 (2)	0.006 (2)
O52	0.0322 (18)	0.065 (3)	0.072 (3)	0.0077 (19)	0.0092 (18)	−0.001 (2)
C11	0.032 (2)	0.036 (2)	0.0213 (19)	0.006 (2)	0.0038 (17)	0.0005 (19)
C12	0.035 (2)	0.047 (3)	0.037 (2)	−0.002 (2)	−0.002 (2)	0.001 (2)
C13	0.038 (3)	0.064 (4)	0.041 (3)	0.005 (3)	−0.001 (2)	0.008 (3)
C14	0.036 (2)	0.074 (4)	0.038 (3)	0.015 (3)	0.006 (2)	0.015 (3)
C15	0.068 (4)	0.051 (3)	0.030 (2)	0.029 (3)	0.011 (2)	0.008 (3)
C16	0.047 (3)	0.035 (2)	0.025 (2)	0.008 (2)	0.005 (2)	0.0023 (19)

Geometric parameters (Å, º) top

N1—C1	1.407 (6)	C7—C8	1.385 (7)
N1—C2	1.413 (6)	C7—H7	0.95
N1—C11	1.443 (6)	N5—O52	1.209 (6)
C1—O1	1.204 (6)	N5—O51	1.242 (6)
C1—C8	1.484 (6)	C11—C16	1.377 (7)
C2—O2	1.211 (5)	C11—C12	1.393 (7)
C2—C3	1.490 (6)	C12—C13	1.389 (7)
C3—C8	1.369 (7)	C12—H12	0.95
C3—C4	1.381 (6)	C13—C14	1.363 (9)
C4—C5	1.398 (6)	C13—H13	0.95
C4—H4	0.95	C14—C15	1.383 (9)
C5—C6	1.363 (7)	C14—H14	0.95
C5—N5	1.490 (6)	C15—C16	1.396 (7)
C6—C7	1.386 (7)	C15—H15	0.95
C6—H6	0.95	C16—H16	0.95

C1—N1—C2	111.0 (4)	C3—C8—C7	122.6 (5)
C1—N1—C11	123.8 (4)	C3—C8—C1	108.7 (4)
C2—N1—C11	125.1 (4)	C7—C8—C1	128.7 (5)
O1—C1—N1	126.7 (4)	O52—N5—O51	124.7 (5)
O1—C1—C8	127.4 (5)	O52—N5—C5	118.2 (5)
N1—C1—C8	106.0 (4)	O51—N5—C5	117.1 (4)
O2—C2—N1	125.4 (4)	C16—C11—C12	121.8 (5)
O2—C2—C3	128.9 (4)	C16—C11—N1	119.4 (4)
N1—C2—C3	105.5 (4)	C12—C11—N1	118.7 (4)
C8—C3—C4	121.6 (4)	C13—C12—C11	118.6 (5)
C8—C3—C2	108.8 (4)	C13—C12—H12	120.7
C4—C3—C2	129.6 (5)	C11—C12—H12	120.7
C3—C4—C5	114.1 (4)	C14—C13—C12	120.7 (6)
C3—C4—H4	122.9	C14—C13—H13	119.7
C5—C4—H4	122.9	C12—C13—H13	119.7
C6—C5—C4	125.7 (4)	C13—C14—C15	120.0 (5)
C6—C5—N5	116.6 (4)	C13—C14—H14	120.0
C4—C5—N5	117.6 (4)	C15—C14—H14	120.0
C5—C6—C7	118.5 (4)	C14—C15—C16	121.1 (5)
C5—C6—H6	120.8	C14—C15—H15	119.4
C7—C6—H6	120.8	C16—C15—H15	119.4
C8—C7—C6	117.4 (5)	C11—C16—C15	117.8 (5)
C8—C7—H7	121.3	C11—C16—H16	121.1
C6—C7—H7	121.3	C15—C16—H16	121.1

C2—N1—C1—O1	−177.5 (4)	C6—C7—C8—C3	−1.5 (7)
C11—N1—C1—O1	−1.2 (7)	C6—C7—C8—C1	179.5 (4)
C2—N1—C1—C8	2.2 (5)	O1—C1—C8—C3	177.3 (5)
C11—N1—C1—C8	178.5 (4)	N1—C1—C8—C3	−2.4 (5)
C1—N1—C2—O2	−177.6 (4)	O1—C1—C8—C7	−3.6 (8)
C11—N1—C2—O2	6.2 (7)	N1—C1—C8—C7	176.7 (5)
C1—N1—C2—C3	−1.2 (5)	C6—C5—N5—O52	−5.0 (7)
C11—N1—C2—C3	−177.5 (4)	C4—C5—N5—O52	174.7 (5)
O2—C2—C3—C8	175.8 (5)	C6—C5—N5—O51	172.8 (5)
N1—C2—C3—C8	−0.3 (5)	C4—C5—N5—O51	−7.5 (7)
O2—C2—C3—C4	−3.6 (8)	C1—N1—C11—C16	39.3 (6)
N1—C2—C3—C4	−179.7 (5)	C2—N1—C11—C16	−145.0 (4)
C8—C3—C4—C5	−1.2 (7)	C1—N1—C11—C12	−141.3 (4)
C2—C3—C4—C5	178.1 (4)	C2—N1—C11—C12	34.5 (6)
C3—C4—C5—C6	0.2 (7)	C16—C11—C12—C13	0.6 (7)
C3—C4—C5—N5	−179.4 (4)	N1—C11—C12—C13	−178.8 (4)
C4—C5—C6—C7	0.1 (8)	C11—C12—C13—C14	−1.6 (8)
N5—C5—C6—C7	179.7 (4)	C12—C13—C14—C15	0.9 (8)
C5—C6—C7—C8	0.5 (7)	C13—C14—C15—C16	0.8 (8)
C4—C3—C8—C7	2.0 (7)	C12—C11—C16—C15	1.0 (7)
C2—C3—C8—C7	−177.5 (4)	N1—C11—C16—C15	−179.6 (4)
C4—C3—C8—C1	−178.9 (4)	C14—C15—C16—C11	−1.7 (7)
C2—C3—C8—C1	1.7 (5)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₄H₈N₂O₄
M_r	268.22
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	120
a, b, c (Å)	11.9288 (6), 7.0604 (2), 13.8337 (7)
V (Å³)	1165.10 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.12 × 0.04 × 0.03

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.963, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	13798, 1554, 1318
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.171, 1.09
No. of reflections	1554
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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−1/2, −z+3/2; (ii) x, y−1, 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

Allen, 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
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
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Flack, H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143–1148. Web of Science CrossRef CAS IUCr Journals Google Scholar
Glidewell, 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
Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland. 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
Voliotis, 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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Volume 61| Part 4| April 2005| Pages o209-o210

doi:10.1107/S0108270105004245

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