N-(4-Chloro­phen­yl)maleimide

Moreno-Fuquen, R.; Pardo-Botero, Z.; Ellena, J.

doi:10.1107/S160053680803016X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1991

doi:10.1107/S160053680803016X

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N-(4-Chlorophenyl)maleimide

Rodolfo Moreno-Fuquen,^a ^* Zulay Pardo-Botero ^a and Javier Ellena ^b

^aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, and ^bInstituto de Física de São Carlos, Universidade de São Paulo, USP, São Carlos, SP, Brazil
^*Correspondence e-mail: rodimo26@yahoo.es

(Received 2 September 2008; accepted 18 September 2008; online 24 September 2008)

In the title compound, C₁₀H₆ClNO₂, the dihedral angle between the benzene and maleimide rings is 47.54 (9)°. Molecules form centrosymmetric dimers through C—H⋯O hydrogen bonds, resulting in rings of graph-set motif R₂²(8) and chains in the [100] direction. Molecules are also linked by C—H⋯Cl hydrogen bonds along [001]. In this same direction, molecules are connected to other neighbouring molecules by C—H⋯O hydrogen bonds, forming edge-fused R₄⁴(24) rings.

Related literature

For general background, see: Etter (1990 ); Howell & Zhang (2006 ); Miller et al. (2000 , 2001 ); Moreno-Fuquen, Valencia, Abonia, Kennedy & Graham (2003 ); Nardelli (1995 ); Sarma & Desiraju (1986 ).

Experimental

Crystal data

C₁₀H₆ClNO₂
M_r = 207.61
Monoclinic, P 2₁ /c
a = 10.6504 (7) Å
b = 3.8589 (2) Å
c = 22.0308 (14) Å
β = 100.741 (3)°
V = 889.57 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 150 K
0.18 × 0.04 × 0.03 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997 ) T_min = 0.951, T_max = 0.982
11729 measured reflections
1646 independent reflections
1231 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.116
S = 1.07
1646 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.93	2.58	3.493 (3)	169
C2—H2⋯O1ⁱⁱ	0.93	2.77	3.659 (3)	161
C5—H5⋯O2ⁱⁱⁱ	0.93	2.58	3.319 (3)	137
C9—H9⋯O2^iv	0.93	2.64	3.326 (3)	131
C9—H9⋯Cl1^v	0.93	2.89	3.551 (3)	129
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z; (iv) -x+1, -y, -z+1; (v) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 2000 ); cell refinement: DENZO; data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: PARST95 (Nardelli, 1995).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803016X/fj2150sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803016X/fj2150Isup2.hkl

checkCIF report

Comment top

It is known that cyclic unsaturated dicarbonyl compounds such as N-substituted maleimides can be used in free-radical-initiated polymerization processes upon exposure to light (Howell & Zhang, 2006). In order to study the possible application of N-(p-chlorophenylmaleimide) (I) in polymerization processes, and to explain its hydrogen bonding patterns, the synthesis and the study of the crystal structure are reported in this work. N-(p-nitrophenylmaleimide) (4NPMI) (Moreno-Fuquen et al., 2003), N-(o-chlorophenylmaleimide) (2ClPMI) systems (Miller et al., 2001) show a close analogy to the title compounds and are thus employed as a basic reference for comparison. Perspective view of (I), showing the atomic numbering scheme, can be seen in Fig.1. In the arylmaleimide systems the value of the dihedral angle between the benzene and imidic rings influences on the polimerization process, and the presence of different substituents in the benzene ring change the value of this angle (Miller et al., 2000). The photochemical properties of arylmaleimide systems depend on the value of this angle. The dihedral angle between benzene and maleimide planes is 42.98 (5)° for 4NPMI, 66.10 (4) ° for 2ClPMI and 47.54 (9)° for (I). The chlorine atoms, which are pending on the aromatic nucleus, tend to steer the crystal structure to a state characterized by a short axis (Sarma & Desiraju, 1986). For (I), the b axis has a small value [3.8589 (2) Å] and a Cl···Cl nonbonded contact is observed at the same distance. The crystal structure of (I) is stabilized by weak intermolecular C—H···O and C—H···Cl hydrogen-bonds (Nardelli, 1995) (Table 1). The molecules of (I) are linked into a three-dimensional framework by a combination of C—H···O and C—H···Cl hydrogen bonds. The formation of the framework can be explained in terms of three-one substructures. In the first substructure, atom C8 in the molecule at (x,y,z) acts as a hydrogen-bond donor to maleimidic atom O1 in the molecule at (-x,1 - y,1 - z) and atom C9 in the molecule at (x,y,z) acts as a hydrogen-bond donor to maleimidic atom O2 in the molecule at (1 - x,1 - y,1 - z). Both interactions generate dimers containing centrosymmetric rings with graph motif R₂²(8) (Etter, 1990) (Fig. 2, supp. material). These dimers are linked by C(5) chains which are running parallel to [100] direction. In the second substructure, atom C9 in the molecule at (x,1/2 - y,-1/2 + z) acts as a hydrogen-bond donor to atom Cl1 in the molecule at (x,y,z), similarly, atom C5 in the molecule at (x,y,z) acts as a hydrogen-bond donor to maleimidic atom O2 in the molecule at (x,1 + y,z) so generating a chain of edge-fused R₄⁴(24) rings along [001] (Fig. 3, supp. material). The third one-dimensional substructure is built by C—H···O hydrogen bonds. Atom C2 in the molecule at (x,y,z) acts as hydrogen bond donor to maleimidic O1 in the molecule at (-x,-1/2 + y,1/2 - z) so generating a C(7) chains in the [010] direction (Fig.4, supp. material). The low value of the dihedral angle between benzene and maleimide planes, allows to conclude that (I) is not a good candidate to use in a photopolymerization process.

Related literature top

For related literature, see: Etter (1990); Howell & Zhang (2006); Miller et al. (2000, 2001); Moreno-Fuquen, Valencia, Abonia, Kennedy & Graham (2003); Nardelli (1995); Sarma & Desiraju (1986). It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···.? etc. Please revise this section as indicated.

Experimental top

All reagents (purchased from Aldrich) and solvents were used as received. Column chromatography was performed using silica gel H60 to purify the intermediates and final products. Thin layer chromatography (TLC) was used to confirm the structure of the individual compounds.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius,2000); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius,2000); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius,2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST95 (Nardelli, 1995).

Figures top

	Fig. 1. An ORTEP-3 (Farrugia, 1997) plot of the (I) compound, with the atomic labelling scheme. The shapes of the ellipsoids correspond to 50% probability contours of atomic displacement and, for the sake of clarity, H atoms are shown as spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure of (I) showing the formation of centrosymmetric R₂²(8) dimmers rings and C(4) chains which are running parallel to the [100] direction. [Symmetry codes: (i) 1 + x,y + z; (ii)1 - x,1 - y,1 - z; (iii) -x,1 - y,1 - z].
	Fig. 3. Part of the crystal structure of (I) showing the formation of C(9) chains and edge-fused R₄⁴(24) rings along [001]. [Symmetry codes: (i) x,1/2 - y,-1/2 + z; (ii) x,1 + y,z; (iii) x,y,-1 + z; (iv) x,1 + y,-1 + z; (v) x,3/2 - y,-1/2 + z; (vi) x,1/2 - y,1/2 + z; (vii) x,1/2 - y,1/2 + z].
	Fig. 4. Part of the crystal structure of (I) showing the formation of C(7) chains along [010]. [Symmetry codes: (i) x,-1 + y,z; (ii) -x,-1/2 + y,1/2 + z; (iii) -x,1/2 + y,1/2 - z; (iv) x,1 + y,z].
	Fig. 5. The formation of the title compound.

N-(4-Chlorophenyl)maleimide top

Crystal data top

C₁₀H₆ClNO₂	F(000) = 424
M_r = 207.61	D_x = 1.550 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 384(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.6504 (7) Å	Cell parameters from 11729 reflections
b = 3.8589 (2) Å	θ = 2.9–25.4°
c = 22.0308 (14) Å	µ = 0.40 mm⁻¹
β = 100.741 (3)°	T = 150 K
V = 889.57 (9) Å³	Needle, pale-yellow
Z = 4	0.18 × 0.04 × 0.03 mm

Data collection top

Bruker–Nonius KappaCCD diffractometer	1646 independent reflections
Radiation source: fine-focus sealed tube	1231 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
ϕ and ω scans	θ_max = 25.4°, θ_min = 3.0°
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997)	h = −12→12
T_min = 0.951, T_max = 0.982	k = −4→4
11729 measured reflections	l = −24→26

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0501P)² + 0.491P] where P = (F_o² + 2F_c²)/3
1646 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₀H₆ClNO₂	V = 889.57 (9) Å³
M_r = 207.61	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6504 (7) Å	µ = 0.40 mm⁻¹
b = 3.8589 (2) Å	T = 150 K
c = 22.0308 (14) Å	0.18 × 0.04 × 0.03 mm
β = 100.741 (3)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	1646 independent reflections
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997)	1231 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.982	R_int = 0.089
11729 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.07	Δρ_max = 0.21 e Å⁻³
1646 reflections	Δρ_min = −0.31 e Å⁻³
128 parameters

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
Cl1	0.26337 (8)	0.6828 (2)	0.13972 (3)	0.0486 (3)
O1	0.04581 (16)	0.6461 (5)	0.40894 (8)	0.0419 (5)
O2	0.45773 (15)	0.2532 (5)	0.43624 (8)	0.0342 (5)
N1	0.25175 (18)	0.4677 (5)	0.40446 (9)	0.0278 (5)
C1	0.2590 (2)	0.6168 (6)	0.21732 (11)	0.0303 (6)
C2	0.1564 (2)	0.4474 (7)	0.23409 (11)	0.0314 (6)
H2	0.0899	0.3657	0.2040	0.038*
C3	0.1537 (2)	0.4004 (6)	0.29608 (11)	0.0282 (6)
H3	0.0852	0.2870	0.3081	0.034*
C4	0.2542 (2)	0.5240 (6)	0.34041 (11)	0.0269 (6)
C5	0.3567 (2)	0.6933 (6)	0.32329 (12)	0.0283 (6)
H5	0.4237	0.7748	0.3532	0.034*
C6	0.3585 (2)	0.7399 (6)	0.26132 (12)	0.0303 (6)
H6	0.4266	0.8541	0.2492	0.036*
C7	0.1462 (2)	0.5170 (7)	0.43329 (12)	0.0323 (6)
C8	0.1852 (2)	0.3901 (7)	0.49762 (11)	0.0340 (6)
H8	0.1336	0.3862	0.5273	0.041*
C9	0.3057 (2)	0.2833 (7)	0.50601 (12)	0.0317 (6)
H9	0.3524	0.1958	0.5427	0.038*
C10	0.3538 (2)	0.3260 (6)	0.44722 (11)	0.0291 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0730 (6)	0.0459 (5)	0.0305 (4)	0.0071 (4)	0.0186 (4)	0.0053 (3)
O1	0.0297 (10)	0.0600 (13)	0.0376 (11)	0.0126 (9)	0.0101 (8)	0.0056 (9)
O2	0.0285 (10)	0.0420 (11)	0.0320 (10)	0.0049 (8)	0.0055 (8)	−0.0004 (8)
N1	0.0251 (11)	0.0339 (12)	0.0249 (11)	0.0031 (9)	0.0061 (9)	0.0013 (9)
C1	0.0401 (15)	0.0260 (14)	0.0262 (14)	0.0073 (11)	0.0102 (11)	0.0018 (11)
C2	0.0325 (14)	0.0296 (14)	0.0304 (15)	0.0052 (11)	0.0009 (11)	−0.0018 (11)
C3	0.0242 (13)	0.0275 (14)	0.0337 (14)	0.0016 (10)	0.0074 (11)	0.0025 (11)
C4	0.0274 (13)	0.0262 (13)	0.0277 (13)	0.0047 (10)	0.0064 (10)	0.0008 (10)
C5	0.0278 (13)	0.0252 (13)	0.0316 (14)	0.0035 (10)	0.0045 (10)	−0.0025 (11)
C6	0.0301 (13)	0.0260 (14)	0.0382 (16)	0.0034 (11)	0.0151 (12)	0.0020 (11)
C7	0.0286 (14)	0.0368 (15)	0.0329 (15)	0.0005 (12)	0.0097 (11)	−0.0052 (12)
C8	0.0361 (15)	0.0392 (16)	0.0288 (14)	−0.0014 (12)	0.0121 (11)	−0.0005 (12)
C9	0.0346 (15)	0.0338 (14)	0.0260 (14)	−0.0009 (12)	0.0036 (11)	−0.0013 (11)
C10	0.0311 (14)	0.0261 (13)	0.0292 (14)	0.0017 (11)	0.0036 (11)	−0.0025 (11)

Geometric parameters (Å, º) top

Cl1—C1	1.738 (2)	C3—H3	0.9300
O1—C7	1.210 (3)	C4—C5	1.384 (3)
O2—C10	1.209 (3)	C5—C6	1.380 (4)
N1—C7	1.404 (3)	C5—H5	0.9300
N1—C10	1.410 (3)	C6—H6	0.9300
N1—C4	1.433 (3)	C7—C8	1.484 (4)
C1—C6	1.380 (4)	C8—C9	1.327 (4)
C1—C2	1.381 (4)	C8—H8	0.9300
C2—C3	1.383 (3)	C9—C10	1.489 (4)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.392 (3)

C7—N1—C10	109.5 (2)	C4—C5—H5	120.4
C7—N1—C4	126.0 (2)	C1—C6—C5	120.0 (2)
C10—N1—C4	124.3 (2)	C1—C6—H6	120.0
C6—C1—C2	121.1 (2)	C5—C6—H6	120.0
C6—C1—Cl1	118.86 (19)	O1—C7—N1	124.8 (2)
C2—C1—Cl1	120.01 (19)	O1—C7—C8	128.8 (2)
C1—C2—C3	119.3 (2)	N1—C7—C8	106.4 (2)
C1—C2—H2	120.4	C9—C8—C7	109.1 (2)
C3—C2—H2	120.4	C9—C8—H8	125.5
C2—C3—C4	119.5 (2)	C7—C8—H8	125.5
C2—C3—H3	120.2	C8—C9—C10	109.0 (2)
C4—C3—H3	120.2	C8—C9—H9	125.5
C5—C4—C3	120.9 (2)	C10—C9—H9	125.5
C5—C4—N1	120.0 (2)	O2—C10—N1	125.3 (2)
C3—C4—N1	119.1 (2)	O2—C10—C9	128.7 (2)
C6—C5—C4	119.2 (2)	N1—C10—C9	106.0 (2)
C6—C5—H5	120.4

C6—C1—C2—C3	0.0 (4)	C10—N1—C7—O1	177.3 (3)
Cl1—C1—C2—C3	−179.27 (18)	C4—N1—C7—O1	−7.5 (4)
C1—C2—C3—C4	−0.1 (4)	C10—N1—C7—C8	−1.2 (3)
C2—C3—C4—C5	0.0 (4)	C4—N1—C7—C8	174.0 (2)
C2—C3—C4—N1	−178.7 (2)	O1—C7—C8—C9	−177.0 (3)
C7—N1—C4—C5	136.1 (3)	N1—C7—C8—C9	1.5 (3)
C10—N1—C4—C5	−49.4 (3)	C7—C8—C9—C10	−1.1 (3)
C7—N1—C4—C3	−45.1 (3)	C7—N1—C10—O2	179.8 (2)
C10—N1—C4—C3	129.4 (3)	C4—N1—C10—O2	4.4 (4)
C3—C4—C5—C6	0.1 (4)	C7—N1—C10—C9	0.6 (3)
N1—C4—C5—C6	178.9 (2)	C4—N1—C10—C9	−174.7 (2)
C2—C1—C6—C5	0.2 (4)	C8—C9—C10—O2	−178.8 (3)
Cl1—C1—C6—C5	179.46 (18)	C8—C9—C10—N1	0.3 (3)
C4—C5—C6—C1	−0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.58	3.493 (3)	169
C2—H2···O1ⁱⁱ	0.93	2.77	3.659 (3)	161
C5—H5···O2ⁱⁱⁱ	0.93	2.58	3.319 (3)	137
C9—H9···O2^iv	0.93	2.64	3.326 (3)	131
C9—H9···Cl1^v	0.93	2.89	3.551 (3)	129

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y−1/2, −z+1/2; (iii) x, y+1, z; (iv) −x+1, −y, −z+1; (v) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₆ClNO₂
M_r	207.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	10.6504 (7), 3.8589 (2), 22.0308 (14)
β (°)	100.741 (3)
V (Å³)	889.57 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.18 × 0.04 × 0.03

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO; Otwinowski & Minor, 1997)
T_min, T_max	0.951, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	11729, 1646, 1231
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.116, 1.07
No. of reflections	1646
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.31

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius,2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PARST95 (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.58	3.493 (3)	169
C2—H2···O1ⁱⁱ	0.93	2.77	3.659 (3)	161
C5—H5···O2ⁱⁱⁱ	0.93	2.58	3.319 (3)	137
C9—H9···O2^iv	0.93	2.64	3.326 (3)	131
C9—H9···Cl1^v	0.93	2.89	3.551 (3)	129

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y−1/2, −z+1/2; (iii) x, y+1, z; (iv) −x+1, −y, −z+1; (v) x, −y+1/2, z+1/2.

Acknowledgements

RMF dedicates this work to the memory of Professor J. Valderrama. RMF is grateful to the Instituto de Química Física Rocasolano, CSIC, Spain, for the use of the license of Cambridge Structural Database System (Allen, 2002 ). This work was partially supported by the Universidad del Valle, Colombia.

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