N-(2-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 54.2 (1)°.

Related literature

For the crystal structures of N-(phen­yl)phthalimides, see: Izotova et al. (2009 ▶); Magomedova et al. (1980 ▶). For that of the 2-ethyl-substituted derivative, see: Fan et al. (2008 ▶).

Experimental

Crystal data

C15H11NO3

M = 253.25

Monoclinic,

a = 11.8505 (2) Å

b = 6.6903 (1) Å

c = 15.3264 (3) Å

β = 106.258 (1)°

V = 1166.54 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 123 K

0.28 × 0.16 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

10672 measured reflections

2682 independent reflections

2190 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.03

2682 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.22 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/S1600536809032826/bt5039sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032826/bt5039Isup2.hkl

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

C15H11NO3	F(000) = 528
Mr = 253.25	Dx = 1.442 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3112 reflections
a = 11.8505 (2) Å	θ = 2.5–28.3°
b = 6.6903 (1) Å	µ = 0.10 mm−1
c = 15.3264 (3) Å	T = 123 K
β = 106.258 (1)°	Irregular, colorless
V = 1166.54 (3) Å3	0.28 × 0.16 × 0.04 mm
Z = 4

Bruker SMART APEX diffractometer	2190 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 27.5°, θmin = 1.9°
ω scans	h = −14→15
10672 measured reflections	k = −8→8
2682 independent reflections	l = −19→19

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.3213P] where P = (Fo2 + 2Fc2)/3
2682 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.76144 (8)	0.26041 (14)	0.47272 (6)	0.0232 (2)
O2	0.74087 (8)	0.35172 (14)	0.76449 (6)	0.0242 (2)
O3	0.89049 (8)	0.63238 (14)	0.56474 (6)	0.0240 (2)
N1	0.78134 (9)	0.32357 (16)	0.62507 (7)	0.0183 (2)
C1	0.71795 (11)	0.28292 (18)	0.53464 (8)	0.0177 (3)
C2	0.59283 (11)	0.26801 (17)	0.53474 (8)	0.0168 (3)
C3	0.49248 (11)	0.23766 (18)	0.46394 (9)	0.0187 (3)
H3	0.4962	0.2240	0.4031	0.022*
C4	0.38571 (11)	0.22777 (19)	0.48501 (9)	0.0205 (3)
H4	0.3149	0.2111	0.4376	0.025*
C5	0.38127 (11)	0.24202 (19)	0.57471 (9)	0.0227 (3)
H5	0.3075	0.2333	0.5875	0.027*
C6	0.48287 (11)	0.26884 (19)	0.64603 (9)	0.0203 (3)
H6	0.4801	0.2758	0.7073	0.024*
C7	0.58786 (11)	0.28491 (18)	0.62405 (8)	0.0178 (3)
C8	0.70848 (11)	0.32285 (18)	0.68350 (8)	0.0180 (3)
C9	0.90625 (10)	0.34589 (19)	0.65589 (8)	0.0183 (3)
C10	0.96165 (11)	0.50402 (19)	0.62429 (8)	0.0187 (3)
C11	1.08374 (11)	0.5197 (2)	0.65517 (8)	0.0226 (3)
H11	1.1233	0.6222	0.6324	0.027*
C12	1.14739 (12)	0.3852 (2)	0.71924 (9)	0.0251 (3)
H12	1.2304	0.3983	0.7409	0.030*
C13	1.09199 (12)	0.2325 (2)	0.75213 (9)	0.0242 (3)
H13	1.1362	0.1429	0.7968	0.029*
C14	0.97095 (11)	0.2121 (2)	0.71899 (9)	0.0217 (3)
H14	0.9323	0.1054	0.7398	0.026*
C15	0.94409 (12)	0.8082 (2)	0.54130 (10)	0.0254 (3)
H15A	0.9847	0.8806	0.5968	0.038*
H15B	0.8835	0.8942	0.5026	0.038*
H15C	1.0009	0.7703	0.5084	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0218 (5)	0.0299 (5)	0.0200 (5)	−0.0019 (4)	0.0091 (4)	−0.0012 (4)
O2	0.0228 (5)	0.0319 (5)	0.0176 (5)	−0.0004 (4)	0.0051 (4)	−0.0019 (4)
O3	0.0189 (5)	0.0231 (5)	0.0292 (5)	−0.0019 (4)	0.0052 (4)	0.0068 (4)
N1	0.0151 (5)	0.0223 (6)	0.0175 (5)	−0.0013 (4)	0.0047 (4)	0.0012 (4)
C1	0.0196 (6)	0.0152 (6)	0.0183 (6)	−0.0002 (4)	0.0054 (5)	0.0018 (5)
C2	0.0174 (6)	0.0138 (6)	0.0199 (6)	0.0000 (4)	0.0066 (5)	0.0019 (4)
C3	0.0211 (6)	0.0160 (6)	0.0187 (6)	0.0010 (5)	0.0049 (5)	0.0006 (5)
C4	0.0173 (6)	0.0180 (6)	0.0240 (6)	0.0000 (5)	0.0019 (5)	0.0002 (5)
C5	0.0176 (6)	0.0235 (7)	0.0282 (7)	−0.0013 (5)	0.0084 (5)	−0.0013 (5)
C6	0.0198 (6)	0.0220 (7)	0.0205 (6)	−0.0007 (5)	0.0079 (5)	−0.0001 (5)
C7	0.0196 (6)	0.0151 (6)	0.0186 (6)	−0.0006 (5)	0.0053 (5)	0.0005 (5)
C8	0.0182 (6)	0.0161 (6)	0.0201 (6)	0.0010 (5)	0.0063 (5)	0.0017 (5)
C9	0.0148 (6)	0.0226 (6)	0.0177 (6)	−0.0009 (5)	0.0047 (5)	−0.0025 (5)
C10	0.0186 (6)	0.0209 (6)	0.0174 (6)	0.0003 (5)	0.0061 (5)	−0.0016 (5)
C11	0.0193 (6)	0.0259 (7)	0.0242 (6)	−0.0044 (5)	0.0089 (5)	−0.0016 (5)
C12	0.0155 (6)	0.0337 (8)	0.0256 (7)	−0.0005 (5)	0.0050 (5)	−0.0022 (6)
C13	0.0206 (7)	0.0296 (7)	0.0217 (6)	0.0042 (5)	0.0045 (5)	0.0029 (5)
C14	0.0214 (7)	0.0237 (7)	0.0212 (6)	0.0004 (5)	0.0080 (5)	0.0016 (5)
C15	0.0270 (7)	0.0205 (7)	0.0296 (7)	−0.0032 (5)	0.0097 (6)	0.0032 (5)

O1—C1	1.2095 (15)	C6—C7	1.3812 (18)
O2—C8	1.2077 (15)	C6—H6	0.9500
O3—C10	1.3604 (15)	C7—C8	1.4862 (17)
O3—C15	1.4296 (16)	C9—C14	1.3818 (18)
N1—C1	1.4057 (16)	C9—C10	1.4010 (18)
N1—C8	1.4073 (16)	C10—C11	1.3946 (17)
N1—C9	1.4301 (15)	C11—C12	1.3885 (19)
C1—C2	1.4865 (17)	C11—H11	0.9500
C2—C3	1.3821 (17)	C12—C13	1.383 (2)
C2—C7	1.3910 (17)	C12—H12	0.9500
C3—C4	1.3923 (18)	C13—C14	1.3879 (18)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.3937 (18)	C14—H14	0.9500
C4—H4	0.9500	C15—H15A	0.9800
C5—C6	1.3927 (18)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800
C10—O3—C15	116.90 (10)	O2—C8—C7	129.18 (12)
C1—N1—C8	111.90 (10)	N1—C8—C7	105.46 (10)
C1—N1—C9	124.33 (10)	C14—C9—C10	120.61 (11)
C8—N1—C9	123.56 (10)	C14—C9—N1	118.93 (11)
O1—C1—N1	124.77 (12)	C10—C9—N1	120.43 (11)
O1—C1—C2	129.54 (11)	O3—C10—C11	124.71 (11)
N1—C1—C2	105.66 (10)	O3—C10—C9	116.50 (11)
C3—C2—C7	121.35 (11)	C11—C10—C9	118.79 (11)
C3—C2—C1	130.42 (11)	C12—C11—C10	119.85 (12)
C7—C2—C1	108.21 (11)	C12—C11—H11	120.1
C2—C3—C4	117.57 (12)	C10—C11—H11	120.1
C2—C3—H3	121.2	C13—C12—C11	121.12 (12)
C4—C3—H3	121.2	C13—C12—H12	119.4
C3—C4—C5	120.89 (12)	C11—C12—H12	119.4
C3—C4—H4	119.6	C12—C13—C14	119.12 (12)
C5—C4—H4	119.6	C12—C13—H13	120.4
C6—C5—C4	121.32 (12)	C14—C13—H13	120.4
C6—C5—H5	119.3	C9—C14—C13	120.42 (12)
C4—C5—H5	119.3	C9—C14—H14	119.8
C7—C6—C5	117.29 (12)	C13—C14—H14	119.8
C7—C6—H6	121.4	O3—C15—H15A	109.5
C5—C6—H6	121.4	O3—C15—H15B	109.5
C6—C7—C2	121.53 (11)	H15A—C15—H15B	109.5
C6—C7—C8	129.88 (12)	O3—C15—H15C	109.5
C2—C7—C8	108.59 (11)	H15A—C15—H15C	109.5
O2—C8—N1	125.34 (11)	H15B—C15—H15C	109.5
C8—N1—C1—O1	−174.23 (12)	C9—N1—C8—C7	−176.91 (11)
C9—N1—C1—O1	0.68 (19)	C6—C7—C8—O2	−1.5 (2)
C8—N1—C1—C2	3.86 (13)	C2—C7—C8—O2	177.74 (13)
C9—N1—C1—C2	178.77 (11)	C6—C7—C8—N1	179.86 (12)
O1—C1—C2—C3	−4.7 (2)	C2—C7—C8—N1	−0.90 (13)
N1—C1—C2—C3	177.31 (12)	C1—N1—C9—C14	−117.21 (13)
O1—C1—C2—C7	173.64 (12)	C8—N1—C9—C14	57.11 (17)
N1—C1—C2—C7	−4.33 (13)	C1—N1—C9—C10	64.41 (16)
C7—C2—C3—C4	1.02 (18)	C8—N1—C9—C10	−121.27 (13)
C1—C2—C3—C4	179.20 (12)	C15—O3—C10—C11	−7.96 (18)
C2—C3—C4—C5	−1.90 (18)	C15—O3—C10—C9	172.06 (11)
C3—C4—C5—C6	0.75 (19)	C14—C9—C10—O3	−177.71 (11)
C4—C5—C6—C7	1.31 (19)	N1—C9—C10—O3	0.64 (17)
C5—C6—C7—C2	−2.21 (19)	C14—C9—C10—C11	2.31 (18)
C5—C6—C7—C8	176.94 (12)	N1—C9—C10—C11	−179.34 (11)
C3—C2—C7—C6	1.07 (19)	O3—C10—C11—C12	177.10 (12)
C1—C2—C7—C6	−177.47 (11)	C9—C10—C11—C12	−2.92 (19)
C3—C2—C7—C8	−178.24 (11)	C10—C11—C12—C13	1.2 (2)
C1—C2—C7—C8	3.22 (13)	C11—C12—C13—C14	1.2 (2)
C1—N1—C8—O2	179.33 (12)	C10—C9—C14—C13	0.07 (19)
C9—N1—C8—O2	4.38 (19)	N1—C9—C14—C13	−178.31 (11)
C1—N1—C8—C7	−1.96 (13)	C12—C13—C14—C9	−1.8 (2)