N-(4-Methoxy-phen-yl)phthalimide.

The phthalimide fused-ring system and the phenyl-ene ring in the title compound, C(15)H(11)NO(3), are inclined at an angle of 60.0 (1)°.

Related literature

For the crystal structures of N-(phen­yl)phthalimides, see: Izotova et al. (2009 ▶); Magomedova et al. (1980 ▶). For the 4-methyl-substituted derivative, see: Bocelli et al. (1995 ▶).

Experimental

Crystal data

C15H11NO3

M = 253.25

Monoclinic,

a = 18.6152 (5) Å

b = 3.8502 (1) Å

c = 16.3125 (4) Å

β = 96.704 (2)°

V = 1161.16 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 123 K

0.40 × 0.06 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

9965 measured reflections

2645 independent reflections

1927 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.01

2645 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032838/bt5040sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032838/bt5040Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H11NO3	F(000) = 528
Mr = 253.25	Dx = 1.449 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2162 reflections
a = 18.6152 (5) Å	θ = 2.6–28.1°
b = 3.8502 (1) Å	µ = 0.10 mm−1
c = 16.3125 (4) Å	T = 123 K
β = 96.704 (2)°	Colorless, prism
V = 1161.16 (5) Å3	0.40 × 0.06 × 0.04 mm
Z = 4

Bruker SMART APEX diffractometer	1927 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
graphite	θmax = 27.5°, θmin = 1.1°
ω scans	h = −24→24
9965 measured reflections	k = −4→4
2645 independent reflections	l = −19→21

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0442P)2 + 0.5469P] where P = (Fo2 + 2Fc2)/3
2645 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.23040 (7)	0.2003 (4)	0.30862 (8)	0.0191 (3)
O1	0.13566 (6)	0.4704 (3)	0.36518 (7)	0.0265 (3)
O2	0.29659 (6)	−0.0742 (3)	0.21493 (7)	0.0249 (3)
O3	0.44516 (6)	0.1734 (3)	0.57594 (7)	0.0240 (3)
C1	0.16067 (8)	0.3406 (4)	0.30709 (10)	0.0195 (3)
C2	0.12587 (8)	0.2999 (4)	0.22082 (10)	0.0187 (3)
C3	0.05760 (8)	0.3925 (4)	0.18527 (10)	0.0214 (4)
H3	0.0239	0.4996	0.2167	0.026*
C4	0.04005 (9)	0.3230 (4)	0.10160 (10)	0.0234 (4)
H4	−0.0068	0.3803	0.0756	0.028*
C5	0.08989 (9)	0.1710 (4)	0.05523 (10)	0.0236 (4)
H5	0.0768	0.1297	−0.0020	0.028*
C6	0.15867 (9)	0.0785 (4)	0.09164 (10)	0.0211 (4)
H6	0.1929	−0.0255	0.0603	0.025*
C7	0.17521 (8)	0.1437 (4)	0.17481 (10)	0.0185 (3)
C8	0.24232 (8)	0.0711 (4)	0.23055 (10)	0.0192 (3)
C9	0.28401 (8)	0.1935 (4)	0.37938 (10)	0.0191 (3)
C10	0.26872 (8)	0.0433 (4)	0.45236 (10)	0.0201 (3)
H10	0.2223	−0.0543	0.4559	0.024*
C11	0.32090 (8)	0.0343 (4)	0.52048 (10)	0.0206 (3)
H11	0.3102	−0.0641	0.5711	0.025*
C12	0.38907 (8)	0.1716 (4)	0.51360 (10)	0.0194 (3)
C13	0.40427 (8)	0.3237 (4)	0.44008 (10)	0.0213 (4)
H13	0.4509	0.4182	0.4360	0.026*
C14	0.35172 (8)	0.3369 (4)	0.37337 (10)	0.0211 (4)
H14	0.3617	0.4435	0.3234	0.025*
C15	0.43407 (9)	0.0139 (5)	0.65216 (10)	0.0255 (4)
H15A	0.4789	0.0251	0.6901	0.038*
H15B	0.4202	−0.2295	0.6424	0.038*
H15C	0.3955	0.1362	0.6764	0.038*

	U11	U22	U33	U12	U13	U23
N1	0.0191 (6)	0.0228 (7)	0.0162 (7)	0.0004 (5)	0.0050 (5)	−0.0009 (5)
O1	0.0258 (6)	0.0341 (7)	0.0207 (6)	0.0032 (5)	0.0080 (5)	−0.0052 (5)
O2	0.0225 (6)	0.0290 (7)	0.0244 (6)	0.0061 (5)	0.0075 (5)	−0.0012 (5)
O3	0.0214 (6)	0.0304 (7)	0.0197 (6)	−0.0022 (5)	0.0010 (5)	0.0021 (5)
C1	0.0199 (8)	0.0188 (8)	0.0210 (8)	−0.0010 (6)	0.0075 (6)	0.0012 (6)
C2	0.0217 (8)	0.0164 (8)	0.0191 (8)	−0.0019 (6)	0.0070 (6)	0.0010 (6)
C3	0.0208 (8)	0.0205 (8)	0.0243 (9)	0.0004 (6)	0.0082 (7)	0.0021 (7)
C4	0.0210 (8)	0.0231 (9)	0.0258 (9)	−0.0016 (7)	0.0021 (7)	0.0047 (7)
C5	0.0287 (9)	0.0231 (9)	0.0188 (8)	−0.0032 (7)	0.0022 (7)	0.0013 (7)
C6	0.0254 (8)	0.0193 (8)	0.0195 (8)	−0.0009 (7)	0.0066 (6)	−0.0001 (7)
C7	0.0212 (8)	0.0161 (8)	0.0194 (8)	−0.0021 (6)	0.0072 (6)	0.0019 (6)
C8	0.0226 (8)	0.0172 (8)	0.0190 (8)	−0.0014 (6)	0.0071 (6)	0.0010 (6)
C9	0.0200 (8)	0.0184 (8)	0.0191 (8)	0.0018 (6)	0.0032 (6)	−0.0019 (6)
C10	0.0194 (8)	0.0205 (8)	0.0213 (9)	−0.0021 (6)	0.0068 (6)	−0.0010 (6)
C11	0.0244 (8)	0.0202 (8)	0.0181 (8)	−0.0001 (6)	0.0064 (6)	0.0005 (6)
C12	0.0203 (8)	0.0174 (8)	0.0204 (8)	0.0023 (6)	0.0028 (6)	−0.0024 (6)
C13	0.0196 (8)	0.0217 (9)	0.0238 (9)	−0.0002 (7)	0.0075 (6)	−0.0003 (7)
C14	0.0237 (8)	0.0211 (8)	0.0200 (8)	−0.0004 (7)	0.0078 (6)	0.0012 (6)
C15	0.0291 (9)	0.0274 (10)	0.0196 (9)	−0.0009 (7)	0.0017 (7)	0.0022 (7)

N1—C1	1.4034 (19)	C6—C7	1.379 (2)
N1—C8	1.409 (2)	C6—H6	0.9500
N1—C9	1.435 (2)	C7—C8	1.483 (2)
O1—C1	1.2114 (19)	C9—C10	1.383 (2)
O2—C8	1.2080 (18)	C9—C14	1.390 (2)
O3—C12	1.3699 (19)	C10—C11	1.388 (2)
O3—C15	1.4232 (19)	C10—H10	0.9500
C1—C2	1.487 (2)	C11—C12	1.391 (2)
C2—C3	1.381 (2)	C11—H11	0.9500
C2—C7	1.389 (2)	C12—C13	1.393 (2)
C3—C4	1.392 (2)	C13—C14	1.377 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.392 (2)	C14—H14	0.9500
C4—H4	0.9500	C15—H15A	0.9800
C5—C6	1.393 (2)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800
C1—N1—C8	111.27 (13)	O2—C8—C7	128.56 (15)
C1—N1—C9	125.17 (13)	N1—C8—C7	106.11 (13)
C8—N1—C9	123.54 (13)	C10—C9—C14	120.42 (15)
C12—O3—C15	118.08 (12)	C10—C9—N1	120.41 (14)
O1—C1—N1	125.74 (15)	C14—C9—N1	119.17 (14)
O1—C1—C2	128.24 (15)	C9—C10—C11	120.29 (14)
N1—C1—C2	106.02 (13)	C9—C10—H10	119.9
C3—C2—C7	121.28 (15)	C11—C10—H10	119.9
C3—C2—C1	130.39 (14)	C10—C11—C12	119.05 (15)
C7—C2—C1	108.33 (14)	C10—C11—H11	120.5
C2—C3—C4	117.47 (15)	C12—C11—H11	120.5
C2—C3—H3	121.3	O3—C12—C11	124.43 (14)
C4—C3—H3	121.3	O3—C12—C13	115.03 (14)
C3—C4—C5	121.23 (15)	C11—C12—C13	120.53 (15)
C3—C4—H4	119.4	C14—C13—C12	119.94 (14)
C5—C4—H4	119.4	C14—C13—H13	120.0
C4—C5—C6	120.88 (16)	C12—C13—H13	120.0
C4—C5—H5	119.6	C13—C14—C9	119.75 (15)
C6—C5—H5	119.6	C13—C14—H14	120.1
C7—C6—C5	117.48 (15)	C9—C14—H14	120.1
C7—C6—H6	121.3	O3—C15—H15A	109.5
C5—C6—H6	121.3	O3—C15—H15B	109.5
C6—C7—C2	121.64 (15)	H15A—C15—H15B	109.5
C6—C7—C8	130.11 (14)	O3—C15—H15C	109.5
C2—C7—C8	108.24 (14)	H15A—C15—H15C	109.5
O2—C8—N1	125.32 (15)	H15B—C15—H15C	109.5
C8—N1—C1—O1	−179.83 (16)	C9—N1—C8—C7	−177.28 (14)
C9—N1—C1—O1	−1.1 (3)	C6—C7—C8—O2	−2.9 (3)
C8—N1—C1—C2	−0.56 (17)	C2—C7—C8—O2	176.86 (16)
C9—N1—C1—C2	178.14 (14)	C6—C7—C8—N1	178.40 (16)
O1—C1—C2—C3	−0.9 (3)	C2—C7—C8—N1	−1.81 (17)
N1—C1—C2—C3	179.88 (16)	C1—N1—C9—C10	55.6 (2)
O1—C1—C2—C7	178.63 (16)	C8—N1—C9—C10	−125.84 (17)
N1—C1—C2—C7	−0.62 (17)	C1—N1—C9—C14	−125.02 (17)
C7—C2—C3—C4	0.1 (2)	C8—N1—C9—C14	53.5 (2)
C1—C2—C3—C4	179.55 (16)	C14—C9—C10—C11	0.1 (2)
C2—C3—C4—C5	−1.0 (2)	N1—C9—C10—C11	179.42 (14)
C3—C4—C5—C6	1.0 (3)	C9—C10—C11—C12	−1.4 (2)
C4—C5—C6—C7	−0.1 (2)	C15—O3—C12—C11	2.2 (2)
C5—C6—C7—C2	−0.9 (2)	C15—O3—C12—C13	−178.34 (14)
C5—C6—C7—C8	178.91 (16)	C10—C11—C12—O3	−179.02 (14)
C3—C2—C7—C6	0.9 (2)	C10—C11—C12—C13	1.6 (2)
C1—C2—C7—C6	−178.69 (14)	O3—C12—C13—C14	−179.87 (14)
C3—C2—C7—C8	−178.96 (14)	C11—C12—C13—C14	−0.4 (2)
C1—C2—C7—C8	1.49 (17)	C12—C13—C14—C9	−0.9 (2)
C1—N1—C8—O2	−177.28 (15)	C10—C9—C14—C13	1.1 (2)
C9—N1—C8—O2	4.0 (2)	N1—C9—C14—C13	−178.24 (14)
C1—N1—C8—C7	1.44 (17)