N-(2-Methoxy­phen­yl)phthalimide

Abstract

The phthalimide fused-ring system and the phenyl­ene ring in the title compound, C₁₅H₁₁NO₃, 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 _r = 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) ų

• 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

• Δρ_max = 0.27 e Å⁻³

• Δρ_min = −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 ▶).

Supplementary Material

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

supplementary crystallographic information

Experimental

Phthalic anhydride (5.00 g, 33.8 mmol) and 4-methoxyaniline (4.99 g, 40.5 mmol) were heated in acetic acid (15 ml) for 4 h. The mixture was cooled and then poured into water. The solid that separated was collected and recrystallized from ethanol in 90% yield.

Refinement

H-atoms were placed in calculated positions (C—H 0.95 or 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 U_eq(C) or 1.5U_eq(C_methyl).

Figures

Fig. 1.

Anisotropic displacement ellipsoid plot (Barbour, 2001) of C15H11NO3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

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

Data collection

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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)