N-(3-Nitro­phenyl)­maleimide

Moreno-Fuquen, R.; Valencia, H.; Pardo, Z.D.; D'Vries, R.; Kennedy, A.R.

doi:10.1107/S1600536806020940

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 7| July 2006| Pages o2734-o2735

https://doi.org/10.1107/S1600536806020940

N-(3-Nitrophenyl)maleimide

Rodolfo Moreno-Fuquen,^a ^* Hoover Valencia,^b Zulay Diney Pardo,^a Richard D'Vries ^a and Alan R. Kennedy ^c

^aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, ^bDepartamento de Química, Facultad de Ciencias, Universidad Tecnológica de Pereira, Pereira, Colombia, and ^cDepartment of Pure and Applied Chemistry, University of Strathclyde, Scotland
^*Correspondence e-mail: rodimo26@yahoo.es

(Received 2 May 2006; accepted 1 June 2006; online 14 June 2006)

The title compound, C₁₀H₆N₂O₄, belongs to a series of N-arylmaleimides, which can be used as photoinitiators for free-radical polymerization. The dihedral angles between the planes of the benzene and imide rings are 56.2 (1) and 52.9 (1)° in the two independent molecules in the asymmetric unit.

Comment

There is considerable activity related to the use of N-substituted maleimides as photoionizers for free-radical polymerization, where the maleimide can produce the initiating radical species (Pyriadi & Nabeel, 1988 ; Andersson et al., 1996 ; Hoyle et al., 1999 ). In continuing the structural studies on N-substituted maleimide systems, to study the behaviour of C_aryl—N distance and imide/benzene interplanar angle, the crystal structure determination of m-nitrophenylmaleimide, C₁₀H₆N₂O₄, (I), was undertaken. The reactivity of N-aromatic maleimides in photopolymerization processes as a function of the angle between the maleimide and benzene rings has been analysed (Miller et al., 2000 ). The p-nitrophenylmaleimide (p-NPM) system has been reported by our research group (Moreno-Fuquen et al., 2003 ). This structure has a close analogy to the title compound and it has been used as a model for comparison.

A perspective view of the two independent molecules in the asymmetric unit of the title compound, showing the atomic numbering scheme, is given in Fig. 1. Focusing on the N—C_aryl bond length, in the title compound the N2—C5 and N4—C15 distances are 1.424 (4) and 1.421 (4) Å, respectively. These values are close to the N—C_aryl bond length for p-nitrophenylmaleimide (Moreno-Fuquen et al., 2003) and are slightly smaller than the average value reported for nine N-arylmaleimide derivatives (Miller et al., 2000). The benzene ring mean plane is rotated 56.2 (1) and 52.9 (1)° with respect to the imide ring mean plane. These values are dictated probably by the weak hydrogen bond between an O atom of the maleimide group and a C atom of the benzene ring. The rotation is smaller in the case of p-NPM, which has an angle of 42.98 (5)°. This is consistent with the literature values, where other maleimides with bulky ortho substituents show angles of rotation greater than 80°. Other bond lengths and internal geometrical parameters of the title compound (Table 1) are similar to those in p-NPM. There are no significant intermolecular hydrogen bonds in the structure.

Figure 1
The asymmetric unit of the title compound with the atomic labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radii.

Experimental

Reagents and solvents for the synthesis were obtained from Aldrich Chemical Co., and were used without additional purification. The title compound was prepared by taking equimolar quantities of m-nitroaniline and maleic anhydride in nitrobenzene and refluxing at 513 K for 3 h. The reaction product was filtered and washed with hexane and then it was dissolved in a mixture of ethyl acetate–hexane (15% hexane) in order to purify it by column chromatography. The solid was crystallized from chloroform, giving pale-yellow prisms with a melting point of 395 (1) K.

Crystal data

C₁₀H₆N₂O₄
M_r = 218.17
Orthorhombic, P n a 2₁
a = 18.9815 (6) Å
b = 6.6643 (2) Å
c = 14.8702 (4) Å
V = 1881.06 (10) Å³
Z = 8
D_x = 1.541 Mg m⁻³
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 123 (2) K
Prism, pale yellow
0.40 × 0.25 × 0.07 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
ω/2θ scans
Absorption correction: none
4072 measured reflections
2238 independent reflections
1693 reflections with I > 2σ(I)
R_int = 0.032
θ_max = 27.5°
2 standard reflections frequency: 150 min intensity decay: 0.1%

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.119
S = 1.05
2238 reflections
289 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0754P)² + 0.0433P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N2—C10	1.393 (4)
N2—C7	1.404 (4)
N2—C5	1.424 (4)
N4—C17	1.400 (5)
N4—C20	1.403 (4)
N4—C15	1.421 (4)
C4—C5	1.394 (5)
C5—C6	1.392 (4)
C8—C9	1.318 (6)
C14—C15	1.383 (4)
C15—C16	1.386 (5)
C18—C19	1.329 (6)

C10—N2—C5	124.8 (3)
C7—N2—C5	124.2 (3)
C17—N4—C15	124.8 (3)
C20—N4—C15	124.8 (3)
C2—C1—N1	118.8 (3)
C16—C11—N3	118.4 (3)

O1—N1—C1—C2	−6.9 (5)
C7—N2—C5—C6	116.7 (4)
O5—N3—C11—C16	175.7 (3)
C20—N4—C15—C16	−47.8 (5)

In the absence of significant anomalous scattering, Friedel pairs were merged. H atoms were located in electron-density difference maps and subsequently treated as riding atoms, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C).

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: CAD-4 SDP (Frenz, 1978 ); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536806020940/cf2029sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806020940/cf2029Isup2.hkl

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 SDP (Frenz, 1978); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

m-Nitrophenylmaleimide top

Crystal data top

C₁₀H₆N₂O₄	D_x = 1.541 Mg m⁻³
M_r = 218.17	Melting point: 395(1) K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 18.9815 (6) Å	θ = 2.6–27.5°
b = 6.6643 (2) Å	µ = 0.12 mm⁻¹
c = 14.8702 (4) Å	T = 123 K
V = 1881.06 (10) Å³	Prism, pale yellow
Z = 8	0.40 × 0.25 × 0.07 mm
F(000) = 896

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.032
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 2.6°
Graphite monochromator	h = −24→24
ω/2θ scans	k = −8→8
4072 measured reflections	l = −19→19
2238 independent reflections	2 standard reflections every 150 min
1693 reflections with I > 2σ(I)	intensity decay: 0.1%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0754P)² + 0.0433P] where P = (F_o² + 2F_c²)/3
2238 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.39 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
O1	0.55002 (13)	0.9037 (4)	0.9815 (2)	0.0418 (7)
O2	0.61359 (13)	1.1499 (4)	1.0305 (2)	0.0336 (6)
O3	0.91013 (14)	0.7232 (5)	1.0915 (2)	0.0443 (7)
O4	0.84956 (12)	1.2131 (4)	0.8924 (2)	0.0330 (6)
O5	0.81692 (13)	0.5768 (4)	0.7350 (2)	0.0373 (6)
O6	0.88410 (13)	0.3317 (3)	0.6919 (2)	0.0324 (6)
O7	1.17689 (15)	0.7919 (5)	0.6292 (2)	0.0474 (8)
O8	1.11689 (14)	0.2920 (3)	0.82382 (19)	0.0310 (6)
N1	0.60690 (15)	0.9805 (4)	0.9992 (2)	0.0288 (7)
N2	0.86358 (14)	0.9338 (4)	0.98297 (19)	0.0237 (6)
N3	0.87500 (15)	0.5040 (4)	0.7210 (2)	0.0281 (7)
N4	1.13008 (15)	0.5751 (4)	0.73457 (19)	0.0237 (6)
C1	0.67096 (18)	0.8626 (5)	0.9812 (2)	0.0254 (8)
C2	0.6639 (2)	0.6636 (5)	0.9546 (2)	0.0282 (8)
H2	0.6188	0.6041	0.9476	0.034*
C3	0.7248 (2)	0.5549 (5)	0.9387 (3)	0.0320 (8)
H3	0.7216	0.4178	0.9217	0.038*
C4	0.7910 (2)	0.6447 (5)	0.9473 (3)	0.0279 (8)
H4	0.8326	0.5699	0.9350	0.033*
C5	0.79573 (18)	0.8449 (5)	0.9739 (2)	0.0239 (8)
C6	0.73525 (17)	0.9557 (5)	0.9921 (2)	0.0240 (7)
H6	0.7382	1.0913	1.0114	0.029*
C7	0.91483 (18)	0.8697 (6)	1.0447 (3)	0.0303 (8)
C8	0.97290 (19)	1.0196 (6)	1.0392 (3)	0.0360 (9)
H8	1.0162	1.0124	1.0712	0.043*
C9	0.95494 (19)	1.1638 (5)	0.9830 (3)	0.0323 (8)
H9	0.9827	1.2780	0.9686	0.039*
C10	0.88335 (19)	1.1171 (5)	0.9458 (3)	0.0258 (7)
C11	0.93765 (18)	0.6284 (5)	0.7381 (2)	0.0232 (7)
C12	0.92815 (18)	0.8288 (5)	0.7621 (2)	0.0272 (8)
H12	0.8824	0.8839	0.7696	0.033*
C13	0.9875 (2)	0.9439 (5)	0.7746 (3)	0.0295 (8)
H13	0.9828	1.0820	0.7893	0.035*
C14	1.05406 (19)	0.8610 (5)	0.7661 (2)	0.0266 (8)
H14	1.0945	0.9420	0.7757	0.032*
C15	1.06188 (17)	0.6608 (4)	0.7437 (2)	0.0229 (7)
C16	1.00312 (17)	0.5423 (5)	0.7282 (2)	0.0225 (7)
H16	1.0079	0.4055	0.7111	0.027*
C17	1.18201 (18)	0.6437 (6)	0.6752 (3)	0.0324 (8)
C18	1.24049 (19)	0.4970 (6)	0.6797 (3)	0.0361 (9)
H18	1.2836	0.5061	0.6475	0.043*
C19	1.22294 (19)	0.3507 (5)	0.7361 (3)	0.0332 (8)
H19	1.2515	0.2386	0.7511	0.040*
C20	1.15106 (18)	0.3915 (5)	0.7721 (2)	0.0255 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0213 (14)	0.0482 (16)	0.0558 (18)	−0.0019 (11)	−0.0034 (12)	0.0033 (15)
O2	0.0333 (15)	0.0317 (13)	0.0357 (14)	0.0089 (11)	0.0003 (11)	−0.0034 (12)
O3	0.0297 (14)	0.0605 (18)	0.0427 (17)	0.0091 (13)	0.0019 (12)	0.0226 (16)
O4	0.0307 (13)	0.0293 (13)	0.0389 (14)	0.0035 (11)	−0.0014 (12)	−0.0011 (13)
O5	0.0227 (14)	0.0427 (14)	0.0465 (16)	0.0052 (11)	0.0025 (12)	0.0015 (14)
O6	0.0274 (14)	0.0299 (12)	0.0398 (15)	−0.0047 (10)	0.0007 (11)	−0.0053 (12)
O7	0.0312 (15)	0.0609 (19)	0.0501 (18)	−0.0012 (13)	0.0023 (13)	0.0282 (17)
O8	0.0369 (14)	0.0231 (11)	0.0331 (14)	0.0005 (10)	0.0011 (11)	0.0039 (12)
N1	0.0223 (16)	0.0373 (16)	0.0268 (17)	0.0027 (12)	0.0006 (12)	0.0024 (14)
N2	0.0192 (14)	0.0257 (14)	0.0262 (14)	0.0016 (11)	−0.0003 (12)	0.0003 (13)
N3	0.0265 (17)	0.0298 (15)	0.0281 (17)	0.0009 (13)	0.0011 (13)	0.0014 (14)
N4	0.0228 (14)	0.0224 (13)	0.0259 (15)	−0.0012 (11)	−0.0021 (12)	0.0011 (13)
C1	0.0230 (18)	0.0306 (18)	0.0226 (18)	0.0012 (14)	−0.0027 (14)	0.0028 (15)
C2	0.030 (2)	0.0311 (18)	0.0231 (18)	−0.0067 (15)	−0.0055 (15)	−0.0016 (15)
C3	0.039 (2)	0.0244 (17)	0.0324 (19)	0.0001 (16)	0.0005 (17)	−0.0061 (16)
C4	0.032 (2)	0.0256 (17)	0.0262 (18)	0.0048 (14)	0.0022 (15)	−0.0010 (14)
C5	0.0264 (19)	0.0228 (17)	0.0225 (17)	0.0014 (13)	−0.0010 (14)	0.0001 (14)
C6	0.0275 (19)	0.0218 (15)	0.0225 (17)	0.0007 (13)	−0.0039 (15)	−0.0006 (15)
C7	0.0221 (17)	0.044 (2)	0.0248 (19)	0.0082 (16)	0.0021 (15)	0.0038 (17)
C8	0.0180 (18)	0.060 (3)	0.030 (2)	0.0011 (17)	0.0026 (16)	−0.0065 (19)
C9	0.0289 (19)	0.036 (2)	0.0322 (19)	−0.0068 (14)	0.0047 (16)	−0.0083 (17)
C10	0.0305 (19)	0.0211 (16)	0.0259 (18)	0.0012 (13)	0.0013 (15)	−0.0025 (15)
C11	0.0243 (18)	0.0264 (16)	0.0191 (16)	−0.0019 (13)	0.0015 (14)	−0.0007 (14)
C12	0.0248 (19)	0.0300 (18)	0.027 (2)	0.0042 (14)	0.0049 (15)	−0.0019 (15)
C13	0.041 (2)	0.0191 (15)	0.0281 (19)	0.0035 (15)	0.0051 (17)	0.0000 (16)
C14	0.033 (2)	0.0227 (16)	0.0242 (18)	−0.0028 (14)	0.0021 (16)	0.0020 (14)
C15	0.0232 (18)	0.0231 (16)	0.0224 (16)	0.0009 (13)	0.0021 (14)	0.0033 (14)
C16	0.0257 (17)	0.0221 (16)	0.0197 (17)	0.0014 (13)	0.0011 (14)	−0.0003 (14)
C17	0.0232 (18)	0.046 (2)	0.0284 (19)	−0.0071 (16)	−0.0047 (16)	0.0102 (18)
C18	0.024 (2)	0.055 (2)	0.0290 (19)	0.0010 (17)	0.0001 (16)	0.0011 (17)
C19	0.0251 (18)	0.0362 (18)	0.038 (2)	0.0069 (15)	−0.0074 (17)	−0.0062 (18)
C20	0.0289 (19)	0.0225 (16)	0.0252 (17)	0.0029 (13)	−0.0061 (15)	−0.0062 (15)

Geometric parameters (Å, º) top

O1—N1	1.223 (4)	C4—H4	0.950
O2—N1	1.228 (4)	C5—C6	1.392 (4)
O3—C7	1.202 (5)	C6—H6	0.950
O4—C10	1.204 (4)	C7—C8	1.490 (5)
O5—N3	1.222 (4)	C8—C9	1.318 (6)
O6—N3	1.239 (3)	C8—H8	0.950
O7—C17	1.205 (5)	C9—C10	1.500 (5)
O8—C20	1.205 (5)	C9—H9	0.950
N1—C1	1.473 (4)	C11—C16	1.377 (5)
N2—C10	1.393 (4)	C11—C12	1.394 (4)
N2—C7	1.404 (4)	C12—C13	1.375 (5)
N2—C5	1.424 (4)	C12—H12	0.950
N3—C11	1.472 (4)	C13—C14	1.385 (5)
N4—C17	1.400 (5)	C13—H13	0.950
N4—C20	1.403 (4)	C14—C15	1.383 (4)
N4—C15	1.421 (4)	C14—H14	0.950
C1—C6	1.379 (5)	C15—C16	1.386 (5)
C1—C2	1.390 (5)	C16—H16	0.950
C2—C3	1.385 (5)	C17—C18	1.481 (5)
C2—H2	0.950	C18—C19	1.329 (6)
C3—C4	1.398 (5)	C18—H18	0.950
C3—H3	0.950	C19—C20	1.490 (5)
C4—C5	1.394 (5)	C19—H19	0.950

O1—N1—O2	123.9 (3)	C8—C9—C10	108.5 (3)
O1—N1—C1	117.8 (3)	C8—C9—H9	125.7
O2—N1—C1	118.3 (3)	C10—C9—H9	125.7
C10—N2—C7	109.9 (3)	O4—C10—N2	125.7 (3)
C10—N2—C5	124.8 (3)	O4—C10—C9	128.0 (3)
C7—N2—C5	124.2 (3)	N2—C10—C9	106.2 (3)
O5—N3—O6	123.6 (3)	C16—C11—C12	122.9 (3)
O5—N3—C11	118.4 (3)	C16—C11—N3	118.4 (3)
O6—N3—C11	118.0 (3)	C12—C11—N3	118.6 (3)
C17—N4—C20	109.6 (3)	C13—C12—C11	117.6 (3)
C17—N4—C15	124.8 (3)	C13—C12—H12	121.2
C20—N4—C15	124.8 (3)	C11—C12—H12	121.2
C6—C1—C2	123.2 (3)	C12—C13—C14	120.8 (3)
C6—C1—N1	118.0 (3)	C12—C13—H13	119.6
C2—C1—N1	118.8 (3)	C14—C13—H13	119.6
C3—C2—C1	117.9 (3)	C15—C14—C13	120.3 (3)
C3—C2—H2	121.1	C15—C14—H14	119.8
C1—C2—H2	121.1	C13—C14—H14	119.8
C2—C3—C4	120.7 (3)	C14—C15—C16	120.2 (3)
C2—C3—H3	119.6	C14—C15—N4	120.5 (3)
C4—C3—H3	119.6	C16—C15—N4	119.2 (3)
C5—C4—C3	119.5 (3)	C11—C16—C15	118.1 (3)
C5—C4—H4	120.2	C11—C16—H16	121.0
C3—C4—H4	120.2	C15—C16—H16	121.0
C6—C5—C4	120.7 (3)	O7—C17—N4	124.7 (3)
C6—C5—N2	120.4 (3)	O7—C17—C18	128.9 (4)
C4—C5—N2	118.9 (3)	N4—C17—C18	106.5 (3)
C1—C6—C5	117.9 (3)	C19—C18—C17	109.0 (3)
C1—C6—H6	121.0	C19—C18—H18	125.5
C5—C6—H6	121.0	C17—C18—H18	125.5
O3—C7—N2	125.0 (3)	C18—C19—C20	108.8 (3)
O3—C7—C8	129.2 (3)	C18—C19—H19	125.6
N2—C7—C8	105.8 (3)	C20—C19—H19	125.6
C9—C8—C7	109.4 (3)	O8—C20—N4	125.5 (3)
C9—C8—H8	125.3	O8—C20—C19	128.4 (3)
C7—C8—H8	125.3	N4—C20—C19	106.1 (3)

O1—N1—C1—C6	173.4 (3)	O5—N3—C11—C16	175.7 (3)
O2—N1—C1—C6	−6.3 (5)	O6—N3—C11—C16	−5.3 (5)
O1—N1—C1—C2	−6.9 (5)	O5—N3—C11—C12	−5.4 (5)
O2—N1—C1—C2	173.4 (3)	O6—N3—C11—C12	173.6 (3)
C6—C1—C2—C3	0.1 (5)	C16—C11—C12—C13	1.1 (5)
N1—C1—C2—C3	−179.5 (3)	N3—C11—C12—C13	−177.7 (3)
C1—C2—C3—C4	−1.4 (5)	C11—C12—C13—C14	−1.8 (5)
C2—C3—C4—C5	1.3 (6)	C12—C13—C14—C15	0.8 (6)
C3—C4—C5—C6	0.1 (5)	C13—C14—C15—C16	1.0 (5)
C3—C4—C5—N2	179.5 (3)	C13—C14—C15—N4	179.8 (3)
C10—N2—C5—C6	−50.0 (5)	C17—N4—C15—C14	−57.8 (5)
C7—N2—C5—C6	116.7 (4)	C20—N4—C15—C14	133.5 (4)
C10—N2—C5—C4	130.6 (4)	C17—N4—C15—C16	121.0 (4)
C7—N2—C5—C4	−62.7 (5)	C20—N4—C15—C16	−47.8 (5)
C2—C1—C6—C5	1.2 (5)	C12—C11—C16—C15	0.6 (5)
N1—C1—C6—C5	−179.2 (3)	N3—C11—C16—C15	179.5 (3)
C4—C5—C6—C1	−1.3 (5)	C14—C15—C16—C11	−1.7 (5)
N2—C5—C6—C1	179.3 (3)	N4—C15—C16—C11	179.5 (3)
C10—N2—C7—O3	175.1 (4)	C20—N4—C17—O7	175.6 (4)
C5—N2—C7—O3	6.7 (6)	C15—N4—C17—O7	5.4 (6)
C10—N2—C7—C8	−4.5 (4)	C20—N4—C17—C18	−2.9 (4)
C5—N2—C7—C8	−172.9 (3)	C15—N4—C17—C18	−173.1 (3)
O3—C7—C8—C9	−176.2 (4)	O7—C17—C18—C19	−176.9 (4)
N2—C7—C8—C9	3.3 (4)	N4—C17—C18—C19	1.5 (4)
C7—C8—C9—C10	−1.0 (4)	C17—C18—C19—C20	0.4 (4)
C7—N2—C10—O4	−178.0 (3)	C17—N4—C20—O8	−178.0 (3)
C5—N2—C10—O4	−9.7 (6)	C15—N4—C20—O8	−7.7 (6)
C7—N2—C10—C9	3.9 (4)	C17—N4—C20—C19	3.1 (4)
C5—N2—C10—C9	172.3 (3)	C15—N4—C20—C19	173.3 (3)
C8—C9—C10—O4	−179.8 (4)	C18—C19—C20—O8	178.9 (4)
C8—C9—C10—N2	−1.8 (4)	C18—C19—C20—N4	−2.1 (4)

Acknowledgements

We are grateful to the Instituto de Química Física Rocasolano, CSIC, Spain, for the use of the Cambridge Structural Database System. The authors also acknowledge the Universidad del Valle, Colombia for partial financial support.

References

Andersson, H., Gedde, U. W. & Hult, A. (1996). Macromolecules, 29, 1649–1654. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Version 5.0. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Frenz, B. A. (1978). Computing in Crystallography, edited by H. Schenk, R. Olthof-Hazekamp, H. van Koningsveld & G. C. Bassi, pp. 64-71. Delft: University Press. Google Scholar
Hoyle, C. E., Viswanathan, K., Clark, S. C., Miller, C. W., Nguyen, C., Jonsson, S. & Shao, L. (1999). Macromolecules, 32, 2793–2795. Web of Science CrossRef CAS Google Scholar
Miller, C. W., Hoyle, C. E., Valente, E. J., Zubkowski, J. D. & Jonsson, E. S. (2000). J. Chem. Crystallogr. 30, 563–571. Web of Science CSD CrossRef CAS Google Scholar
Moreno-Fuquen, R., Valencia, H., Abonia, R., Kennedy, A. R. & Graham, D. (2003). Acta Cryst. E59, o1717–o1718. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pyriadi, T. M. & Nabeel, E. (1988). J. Macromol. Sci. Chem. A, 25, 1683–1688. CrossRef Google Scholar
Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany. Google Scholar

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.