N-(2-Ethyl­phen­yl)phthalimide

Fan, Y.M.; Zakaria, N.; Ariffin, A.; Ng, S.W.

doi:10.1107/S1600536808020448

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1699

doi:10.1107/S1600536808020448

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N-(2-Ethylphenyl)phthalimide

Yen May Fan,^a Norzalida Zakaria,^a Azhar Ariffin ^a ^* and Seik Weng Ng ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: azahar70@um.edu.my

(Received 2 July 2008; accepted 3 July 2008; online 6 August 2008)

In the title compound, C₁₆H₁₃NO₂, the phthalimide and benzene ring systems form a dihedral angle of 77.2 (1)°.

Related literature

The crystal structures of a number of phenyl-substituted N-phenylphthalimides have been reported. For the 2-tolyl analogue, see: Bocelli & Cantoni (1989 ). For the 2,4-dimethylphenyl analogue, see: Magnomedova et al. (1980 ); Shahzadi et al. (2006 ). For the 2,6-dimethylphenyl and 2,4,6-trimethylphenyl analogues, see: Voliotis et al. (1984 ). For background literature on kinetic studies, see: Sim et al. (2006 , 2007 ).

Experimental

Crystal data

C₁₆H₁₃NO₂
M_r = 251.27
Orthorhombic, P b c a
a = 15.344 (2) Å
b = 7.7731 (8) Å
c = 21.693 (2) Å
V = 2587.4 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (2) K
0.15 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
15518 measured reflections
2961 independent reflections
2204 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.104
S = 1.01
2961 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020448/tk2280sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020448/tk2280Isup2.hkl

checkCIF report

Comment top

In our studies aimed at understanding the nature of intramolecular general base (IGB) and intramolecular general acid (IGA) catalysis in the hydrolysis of N-substituted phthalimides, we required the preparation of N-phenylphthalimides having a substituent at either the ortho- and/or the para-position. The title compound (I, Fig. 1) is an such an example. In (I), the phthalimido and phenylene portions are flat and are inclined at an angle of 77.2 (1)°.

Related literature top

The crystal structures of a number of phenyl-substituted N-phenylphthalimides have been reported. For the 2-tolyl analogue, see: Bocelli & Cantoni (1989). For the 2,4-dimethylphenyl analogue, see: Magnomedova et al. (1980); Shahzadi et al. (2006). For the 2,6-dimethylphenyl and 2,4,6-trimethylphenyl analogues, see: Voliotis et al. (1984). For background literature on kinetic studies, see: Sim et al. (2006, 2007).

Experimental top

Phthalic anhydride (5.0 g, 33.8 mmol) and o-ethylaniline (4.91 g, 40.5 mmol) were dissolved in glacial acetic acid (15 ml). The mixture was heated at 393–413 K for 4 h; the completion of the reaction was monitored by thin layer chromatography. The mixture was quenched with water. The solid that separated was collected and recrystallized twice from ethanol to give colorless crystals of (I) in 90% yield.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. Molecular structure of (I) drawn at the 70% probability level showing atom labelling. Hydrogen atoms are drawn as spheres of arbitrary radiius.

N-(2-Ethylphenyl)phthalimide top

Crystal data top

C₁₆H₁₃NO₂	F(000) = 1056
M_r = 251.27	D_x = 1.290 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2189 reflections
a = 15.344 (2) Å	θ = 2.3–24.0°
b = 7.7731 (8) Å	µ = 0.09 mm⁻¹
c = 21.693 (2) Å	T = 100 K
V = 2587.4 (5) Å³	Irregular block, colourless
Z = 8	0.15 × 0.10 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	2204 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = −19→11
15518 measured reflections	k = −10→10
2961 independent reflections	l = −28→28

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) = 0.104	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0466P)² + 0.7719P] where P = (F_o² + 2F_c²)/3
2961 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₆H₁₃NO₂	V = 2587.4 (5) Å³
M_r = 251.27	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.344 (2) Å	µ = 0.09 mm⁻¹
b = 7.7731 (8) Å	T = 100 K
c = 21.693 (2) Å	0.15 × 0.10 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	2204 reflections with I > 2σ(I)
15518 measured reflections	R_int = 0.054
2961 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	Δρ_max = 0.27 e Å⁻³
2961 reflections	Δρ_min = −0.19 e Å⁻³
172 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.48223 (7)	0.23894 (15)	0.51820 (5)	0.0271 (3)
O2	0.35501 (7)	0.02107 (14)	0.69268 (5)	0.0251 (3)
N1	0.44007 (8)	0.11973 (15)	0.61157 (5)	0.0171 (3)
C1	0.42560 (10)	0.19354 (18)	0.55323 (6)	0.0181 (3)
C2	0.32925 (9)	0.20247 (18)	0.54575 (6)	0.0166 (3)
C3	0.28005 (10)	0.2658 (2)	0.49751 (7)	0.0204 (3)
H3	0.3066	0.3137	0.4619	0.024*
C4	0.18974 (10)	0.2565 (2)	0.50335 (7)	0.0217 (3)
H4	0.1538	0.2979	0.4709	0.026*
C5	0.15121 (10)	0.1874 (2)	0.55597 (7)	0.0226 (3)
H5	0.0895	0.1819	0.5586	0.027*
C6	0.20135 (10)	0.12648 (19)	0.60476 (7)	0.0203 (3)
H6	0.1752	0.0812	0.6410	0.024*
C7	0.29078 (10)	0.13462 (18)	0.59830 (6)	0.0173 (3)
C8	0.36106 (9)	0.08198 (18)	0.64160 (7)	0.0176 (3)
C9	0.52461 (9)	0.09843 (18)	0.63950 (6)	0.0162 (3)
C10	0.57623 (10)	−0.03944 (19)	0.62150 (7)	0.0201 (3)
H10	0.5564	−0.1168	0.5907	0.024*
C11	0.65713 (10)	−0.0634 (2)	0.64893 (7)	0.0221 (3)
H11	0.6929	−0.1572	0.6368	0.027*
C12	0.68547 (10)	0.0498 (2)	0.69407 (7)	0.0222 (3)
H12	0.7405	0.0330	0.7132	0.027*
C13	0.63332 (10)	0.18808 (19)	0.71133 (7)	0.0208 (3)
H13	0.6535	0.2653	0.7421	0.025*
C14	0.55168 (10)	0.21587 (18)	0.68431 (6)	0.0174 (3)
C15	0.49902 (10)	0.37245 (19)	0.70174 (7)	0.0215 (3)
H15A	0.5072	0.3970	0.7462	0.026*
H15B	0.4364	0.3489	0.6947	0.026*
C16	0.52646 (11)	0.5296 (2)	0.66405 (8)	0.0293 (4)
H16A	0.4912	0.6290	0.6763	0.044*
H16B	0.5175	0.5061	0.6201	0.044*
H16C	0.5882	0.5542	0.6716	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0171 (6)	0.0436 (7)	0.0207 (6)	−0.0029 (5)	0.0029 (5)	0.0057 (5)
O2	0.0185 (6)	0.0354 (6)	0.0215 (5)	−0.0017 (5)	−0.0006 (5)	0.0095 (5)
N1	0.0125 (6)	0.0226 (6)	0.0161 (6)	−0.0005 (5)	−0.0006 (5)	0.0014 (5)
C1	0.0171 (8)	0.0212 (7)	0.0160 (7)	−0.0012 (6)	−0.0001 (6)	−0.0013 (6)
C2	0.0144 (7)	0.0177 (7)	0.0176 (7)	−0.0006 (6)	−0.0005 (6)	−0.0015 (5)
C3	0.0192 (8)	0.0248 (8)	0.0173 (7)	0.0003 (6)	−0.0008 (6)	0.0004 (6)
C4	0.0195 (8)	0.0238 (8)	0.0217 (7)	0.0036 (6)	−0.0062 (6)	0.0004 (6)
C5	0.0117 (7)	0.0279 (8)	0.0283 (8)	0.0010 (6)	−0.0013 (6)	−0.0007 (7)
C6	0.0157 (8)	0.0238 (8)	0.0215 (7)	−0.0013 (6)	0.0015 (6)	0.0021 (6)
C7	0.0163 (7)	0.0173 (7)	0.0183 (7)	0.0009 (6)	−0.0012 (6)	0.0001 (6)
C8	0.0148 (7)	0.0191 (7)	0.0191 (7)	−0.0006 (6)	−0.0005 (6)	−0.0004 (6)
C9	0.0106 (7)	0.0216 (7)	0.0164 (7)	−0.0016 (6)	0.0002 (6)	0.0035 (5)
C10	0.0193 (8)	0.0222 (8)	0.0188 (7)	−0.0014 (6)	−0.0007 (6)	−0.0025 (6)
C11	0.0177 (8)	0.0236 (8)	0.0251 (8)	0.0048 (6)	0.0018 (6)	0.0001 (6)
C12	0.0146 (8)	0.0265 (8)	0.0254 (8)	−0.0003 (6)	−0.0032 (6)	0.0029 (6)
C13	0.0173 (8)	0.0240 (8)	0.0211 (7)	−0.0041 (6)	−0.0029 (6)	−0.0009 (6)
C14	0.0149 (7)	0.0195 (7)	0.0179 (7)	−0.0010 (6)	0.0007 (6)	0.0013 (6)
C15	0.0189 (8)	0.0221 (8)	0.0234 (7)	0.0017 (6)	−0.0025 (6)	−0.0032 (6)
C16	0.0270 (9)	0.0239 (8)	0.0369 (9)	0.0032 (7)	−0.0026 (7)	0.0028 (7)

Geometric parameters (Å, º) top

O1—C1	1.2072 (17)	C9—C10	1.389 (2)
O2—C8	1.2085 (17)	C9—C14	1.397 (2)
N1—C1	1.4071 (18)	C10—C11	1.389 (2)
N1—C8	1.4072 (18)	C10—H10	0.9500
N1—C9	1.4412 (18)	C11—C12	1.387 (2)
C1—C2	1.489 (2)	C11—H11	0.9500
C2—C3	1.381 (2)	C12—C13	1.391 (2)
C2—C7	1.3879 (19)	C12—H12	0.9500
C3—C4	1.393 (2)	C13—C14	1.400 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.393 (2)	C14—C15	1.509 (2)
C4—H4	0.9500	C15—C16	1.529 (2)
C5—C6	1.392 (2)	C15—H15A	0.9900
C5—H5	0.9500	C15—H15B	0.9900
C6—C7	1.381 (2)	C16—H16A	0.9800
C6—H6	0.9500	C16—H16B	0.9800
C7—C8	1.488 (2)	C16—H16C	0.9800

C1—N1—C8	111.43 (12)	C14—C9—N1	119.02 (13)
C1—N1—C9	124.54 (12)	C9—C10—C11	119.53 (14)
C8—N1—C9	123.84 (11)	C9—C10—H10	120.2
O1—C1—N1	124.87 (14)	C11—C10—H10	120.2
O1—C1—C2	129.23 (13)	C12—C11—C10	119.83 (14)
N1—C1—C2	105.90 (12)	C12—C11—H11	120.1
C3—C2—C7	121.70 (14)	C10—C11—H11	120.1
C3—C2—C1	129.94 (13)	C11—C12—C13	120.01 (14)
C7—C2—C1	108.36 (12)	C11—C12—H12	120.0
C2—C3—C4	117.13 (14)	C13—C12—H12	120.0
C2—C3—H3	121.4	C12—C13—C14	121.41 (14)
C4—C3—H3	121.4	C12—C13—H13	119.3
C5—C4—C3	121.11 (14)	C14—C13—H13	119.3
C5—C4—H4	119.4	C9—C14—C13	117.17 (13)
C3—C4—H4	119.4	C9—C14—C15	122.84 (13)
C4—C5—C6	121.31 (14)	C13—C14—C15	119.91 (13)
C4—C5—H5	119.3	C14—C15—C16	111.27 (13)
C6—C5—H5	119.3	C14—C15—H15A	109.4
C7—C6—C5	117.18 (14)	C16—C15—H15A	109.4
C7—C6—H6	121.4	C14—C15—H15B	109.4
C5—C6—H6	121.4	C16—C15—H15B	109.4
C6—C7—C2	121.56 (13)	H15A—C15—H15B	108.0
C6—C7—C8	130.07 (13)	C15—C16—H16A	109.5
C2—C7—C8	108.35 (13)	C15—C16—H16B	109.5
O2—C8—N1	124.92 (13)	H16A—C16—H16B	109.5
O2—C8—C7	129.13 (13)	C15—C16—H16C	109.5
N1—C8—C7	105.95 (12)	H16A—C16—H16C	109.5
C10—C9—C14	122.04 (13)	H16B—C16—H16C	109.5
C10—C9—N1	118.94 (13)

C8—N1—C1—O1	179.48 (14)	C9—N1—C8—C7	175.82 (12)
C9—N1—C1—O1	4.4 (2)	C6—C7—C8—O2	−0.6 (3)
C8—N1—C1—C2	−0.23 (15)	C2—C7—C8—O2	178.26 (15)
C9—N1—C1—C2	−175.35 (12)	C6—C7—C8—N1	−179.73 (15)
O1—C1—C2—C3	−0.7 (3)	C2—C7—C8—N1	−0.86 (15)
N1—C1—C2—C3	179.03 (14)	C1—N1—C9—C10	−80.22 (18)
O1—C1—C2—C7	179.98 (15)	C8—N1—C9—C10	105.25 (16)
N1—C1—C2—C7	−0.33 (15)	C1—N1—C9—C14	100.51 (16)
C7—C2—C3—C4	−0.9 (2)	C8—N1—C9—C14	−74.03 (18)
C1—C2—C3—C4	179.78 (14)	C14—C9—C10—C11	0.5 (2)
C2—C3—C4—C5	0.5 (2)	N1—C9—C10—C11	−178.73 (13)
C3—C4—C5—C6	0.5 (2)	C9—C10—C11—C12	0.2 (2)
C4—C5—C6—C7	−1.1 (2)	C10—C11—C12—C13	−0.7 (2)
C5—C6—C7—C2	0.7 (2)	C11—C12—C13—C14	0.4 (2)
C5—C6—C7—C8	179.48 (14)	C10—C9—C14—C13	−0.8 (2)
C3—C2—C7—C6	0.3 (2)	N1—C9—C14—C13	178.48 (12)
C1—C2—C7—C6	179.72 (13)	C10—C9—C14—C15	176.18 (13)
C3—C2—C7—C8	−178.69 (13)	N1—C9—C14—C15	−4.6 (2)
C1—C2—C7—C8	0.73 (15)	C12—C13—C14—C9	0.3 (2)
C1—N1—C8—O2	−178.51 (14)	C12—C13—C14—C15	−176.74 (14)
C9—N1—C8—O2	−3.3 (2)	C9—C14—C15—C16	−92.56 (17)
C1—N1—C8—C7	0.66 (15)	C13—C14—C15—C16	84.31 (17)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO₂
M_r	251.27
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	15.344 (2), 7.7731 (8), 21.693 (2)
V (Å³)	2587.4 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.15 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15518, 2961, 2204
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.104, 1.01
No. of reflections	2961
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.19

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Acknowledgements

The authors are grateful for a SAGA grant (No. 06-02-03-0147) supporting this study and thank the University of Malaya for the purchase of the diffractometer.

References

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