N-(4-Meth-oxy-benz-yl)phthalimide: a triclinic polymorph.

THE TITLE COMPOUND [SYSTEMATIC NAME: 2-(4-meth-oxy-benz-yl)-isoindoline-1,3-dione], C(16)H(13)NO(3), represents a triclinic polymorph of the previously reported monoclinic form [Warzecha et al. (2006 ▶). Acta Cryst. E62, o5450-o5452]. The reaction of potassium phthalimide and 4-meth-oxy-benzyl chloride in dimethyl-formamide gave platelet-shaped crystals; these were harvested and then needle-shaped crystals were deposited. The platelet- and needle-shaped crystals correspond to the triclinic and monoclinic forms, respectively. The N-C-C(ar)-C(ar) torsion angles between the ring systems are -82.66 (14) and 95.28 (13)°, resulting in a roof-shaped conformation. In the crystal, mol-ecules are accumulated by offset face-face π-π inter-actions between phthalimide units [centroid-centroid distances = 3.640 (2) and 3.651 (2) Å], with inter-planar distances of 3.321 (1) and 3.435 (1) Å. Weak inter-molecular C(ar-yl)-H⋯O=C and C(alk-yl)-H⋯O=C contacts form C(8) and C(11) infinite chain motifs, respectively.

Related literature

For the crystal structure of the monoclinic form of the title compound, see: Warzecha et al. (2006b ▶). For a photochemical study of the title compound, see: Warzecha, Görner et al. (2006 ▶). For related compounds, see: Lü et al. (2006 ▶); Warzecha et al. (2006a ▶); Chen et al. (2006 ▶). For graph-set motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C16H13NO3

M = 267.27

Triclinic,

a = 8.190 (3) Å

b = 8.293 (4) Å

c = 11.465 (5) Å

α = 105.794 (5)°

β = 90.8094 (16)°

γ = 118.154 (5)°

V = 651.3 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.35 × 0.30 × 0.05 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.967, T max = 0.995

6640 measured reflections

2951 independent reflections

2256 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.087

S = 0.96

2951 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Yadokari-XG 2009 (Kabuto et al., 2009 ▶), ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812031376/bh2442sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031376/bh2442Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031376/bh2442Isup3.cml

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

C16H13NO3	Z = 2
Mr = 267.27	F(000) = 280
Triclinic, P1	Dx = 1.363 Mg m−3
Hall symbol: -P 1	Melting point: 403 K
a = 8.190 (3) Å	Mo Kα radiation, λ = 0.71075 Å
b = 8.293 (4) Å	Cell parameters from 2075 reflections
c = 11.465 (5) Å	θ = 3.1–27.5°
α = 105.794 (5)°	µ = 0.10 mm−1
β = 90.8094 (16)°	T = 100 K
γ = 118.154 (5)°	Platelet, colourless
V = 651.3 (5) Å3	0.35 × 0.30 × 0.05 mm

Rigaku Saturn724+ diffractometer	2951 independent reflections
Radiation source: fine-focus sealed tube	2256 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.019
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.2°
profile data from ω–scans	h = −10→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→9
Tmin = 0.967, Tmax = 0.995	l = −14→14
6640 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0536P)2] where P = (Fo2 + 2Fc2)/3
2951 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.17 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.24334 (15)	0.63806 (15)	0.48690 (9)	0.0191 (2)
C2	0.28334 (14)	0.51357 (14)	0.54106 (9)	0.0171 (2)
C3	0.38757 (15)	0.55798 (16)	0.65211 (9)	0.0191 (2)
H1	0.4508 (16)	0.6886 (17)	0.7095 (11)	0.023*
C4	0.40053 (15)	0.40875 (16)	0.67783 (10)	0.0214 (2)
H2	0.4719 (16)	0.4320 (16)	0.7563 (11)	0.026*
C5	0.31087 (16)	0.22283 (16)	0.59444 (10)	0.0233 (3)
H3	0.3180 (17)	0.1217 (18)	0.6154 (11)	0.028*
C6	0.20666 (16)	0.17978 (16)	0.48220 (10)	0.0218 (2)
H4	0.1445 (17)	0.0499 (17)	0.4223 (11)	0.026*
C7	0.19461 (14)	0.32803 (15)	0.45735 (9)	0.0185 (2)
C8	0.09817 (15)	0.32978 (15)	0.34721 (9)	0.0204 (2)
C9	0.07198 (16)	0.58653 (18)	0.28326 (10)	0.0234 (2)
H5	−0.0527 (18)	0.4833 (17)	0.2403 (11)	0.028*
H6	0.0580 (17)	0.6973 (18)	0.3337 (12)	0.028*
C10	0.20838 (15)	0.64133 (16)	0.19466 (9)	0.0206 (2)
C11	0.36928 (16)	0.82062 (16)	0.22606 (10)	0.0222 (2)
H7	0.3937 (17)	0.9133 (17)	0.3059 (11)	0.027*
C12	0.49800 (16)	0.86831 (16)	0.14608 (10)	0.0216 (2)
H8	0.6131 (17)	0.9974 (17)	0.1698 (11)	0.026*
C13	0.46131 (15)	0.73395 (16)	0.03122 (9)	0.0198 (2)
C14	0.30067 (16)	0.55359 (16)	−0.00133 (10)	0.0229 (2)
H9	0.2783 (16)	0.4566 (17)	−0.0834 (11)	0.027*
C15	0.17604 (16)	0.50759 (17)	0.08016 (10)	0.0227 (2)
H10	0.0627 (17)	0.3755 (17)	0.0568 (11)	0.027*
C16	0.75343 (15)	0.93637 (17)	−0.02176 (10)	0.0277 (3)
H11	0.7368	1.0498	−0.0019	0.042*
H12	0.8246	0.9363	−0.0897	0.042*
H13	0.8222	0.9402	0.0505	0.042*
O1	0.29209 (11)	0.80774 (11)	0.52998 (7)	0.0264 (2)
O2	0.00784 (11)	0.19931 (11)	0.25296 (7)	0.0285 (2)
N1	0.13193 (13)	0.51842 (13)	0.37221 (8)	0.0202 (2)
O3	0.57369 (10)	0.76553 (11)	−0.05703 (7)	0.0243 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0172 (5)	0.0215 (6)	0.0175 (5)	0.0096 (5)	0.0056 (4)	0.0045 (4)
C2	0.0151 (5)	0.0175 (5)	0.0180 (5)	0.0078 (4)	0.0063 (4)	0.0048 (4)
C3	0.0169 (5)	0.0202 (6)	0.0178 (5)	0.0088 (5)	0.0042 (4)	0.0030 (4)
C4	0.0186 (5)	0.0276 (6)	0.0198 (5)	0.0123 (5)	0.0056 (4)	0.0084 (5)
C5	0.0238 (6)	0.0232 (6)	0.0282 (6)	0.0137 (5)	0.0094 (5)	0.0120 (5)
C6	0.0211 (6)	0.0172 (5)	0.0236 (6)	0.0076 (5)	0.0067 (4)	0.0044 (4)
C7	0.0148 (5)	0.0193 (5)	0.0175 (5)	0.0065 (4)	0.0049 (4)	0.0040 (4)
C8	0.0169 (5)	0.0221 (6)	0.0184 (5)	0.0076 (5)	0.0067 (4)	0.0045 (4)
C9	0.0221 (6)	0.0316 (6)	0.0214 (5)	0.0159 (5)	0.0047 (5)	0.0106 (5)
C10	0.0203 (5)	0.0285 (6)	0.0184 (5)	0.0154 (5)	0.0025 (4)	0.0090 (4)
C11	0.0263 (6)	0.0250 (6)	0.0169 (5)	0.0152 (5)	0.0019 (4)	0.0041 (4)
C12	0.0213 (6)	0.0208 (6)	0.0204 (5)	0.0096 (5)	0.0003 (4)	0.0050 (4)
C13	0.0193 (5)	0.0267 (6)	0.0165 (5)	0.0134 (5)	0.0025 (4)	0.0078 (4)
C14	0.0222 (6)	0.0250 (6)	0.0175 (5)	0.0108 (5)	0.0003 (4)	0.0027 (4)
C15	0.0191 (6)	0.0249 (6)	0.0209 (5)	0.0089 (5)	0.0002 (4)	0.0066 (5)
C16	0.0189 (6)	0.0330 (7)	0.0234 (6)	0.0078 (5)	0.0035 (4)	0.0071 (5)
O1	0.0311 (5)	0.0211 (4)	0.0262 (4)	0.0144 (4)	0.0032 (3)	0.0038 (3)
O2	0.0278 (4)	0.0271 (4)	0.0186 (4)	0.0086 (4)	−0.0012 (3)	−0.0008 (3)
N1	0.0211 (5)	0.0227 (5)	0.0171 (4)	0.0111 (4)	0.0040 (4)	0.0058 (4)
O3	0.0196 (4)	0.0284 (4)	0.0173 (4)	0.0073 (3)	0.0034 (3)	0.0049 (3)

C1—O1	1.2122 (14)	C9—H5	0.974 (13)
C1—N1	1.3956 (14)	C9—H6	1.001 (13)
C1—C2	1.4903 (16)	C10—C11	1.3867 (16)
C2—C3	1.3795 (15)	C10—C15	1.3942 (15)
C2—C7	1.3921 (15)	C11—C12	1.3928 (16)
C3—C4	1.3969 (16)	C11—H7	0.967 (12)
C3—H1	0.974 (12)	C12—C13	1.3929 (15)
C4—C5	1.3928 (16)	C12—H8	0.995 (12)
C4—H2	0.987 (12)	C13—O3	1.3720 (13)
C5—C6	1.3940 (17)	C13—C14	1.3902 (16)
C5—H3	0.959 (13)	C14—C15	1.3834 (15)
C6—C7	1.3808 (16)	C14—H9	1.005 (12)
C6—H4	0.980 (12)	C15—H10	1.004 (12)
C7—C8	1.4871 (16)	C16—O3	1.4286 (14)
C8—O2	1.2129 (13)	C16—H11	0.9800
C8—N1	1.3970 (16)	C16—H12	0.9800
C9—N1	1.4701 (14)	C16—H13	0.9800
C9—C10	1.5135 (15)
O1—C1—N1	124.83 (10)	H5—C9—H6	107.4 (10)
O1—C1—C2	129.26 (10)	C11—C10—C15	118.74 (10)
N1—C1—C2	105.90 (9)	C11—C10—C9	121.47 (10)
C3—C2—C7	121.69 (10)	C15—C10—C9	119.76 (11)
C3—C2—C1	130.35 (10)	C10—C11—C12	121.38 (10)
C7—C2—C1	107.96 (10)	C10—C11—H7	119.2 (7)
C2—C3—C4	117.31 (10)	C12—C11—H7	119.4 (7)
C2—C3—H1	121.1 (7)	C11—C12—C13	118.97 (11)
C4—C3—H1	121.5 (7)	C11—C12—H8	120.6 (7)
C5—C4—C3	121.03 (11)	C13—C12—H8	120.4 (7)
C5—C4—H2	118.2 (7)	O3—C13—C14	115.20 (9)
C3—C4—H2	120.8 (7)	O3—C13—C12	124.59 (10)
C4—C5—C6	121.18 (11)	C14—C13—C12	120.21 (10)
C4—C5—H3	119.5 (7)	C15—C14—C13	119.99 (10)
C6—C5—H3	119.3 (8)	C15—C14—H9	120.7 (7)
C7—C6—C5	117.47 (10)	C13—C14—H9	119.3 (7)
C7—C6—H4	120.6 (7)	C14—C15—C10	120.69 (11)
C5—C6—H4	121.9 (7)	C14—C15—H10	119.3 (7)
C6—C7—C2	121.32 (11)	C10—C15—H10	120.0 (7)
C6—C7—C8	130.48 (10)	O3—C16—H11	109.5
C2—C7—C8	108.19 (10)	O3—C16—H12	109.5
O2—C8—N1	124.84 (11)	H11—C16—H12	109.5
O2—C8—C7	129.29 (11)	O3—C16—H13	109.5
N1—C8—C7	105.88 (9)	H11—C16—H13	109.5
N1—C9—C10	112.27 (9)	H12—C16—H13	109.5
N1—C9—H5	106.8 (7)	C1—N1—C8	112.06 (9)
C10—C9—H5	111.5 (7)	C1—N1—C9	123.97 (10)
N1—C9—H6	105.7 (7)	C8—N1—C9	123.73 (9)
C10—C9—H6	112.7 (7)	C13—O3—C16	117.23 (8)
O1—C1—C2—C3	−1.23 (19)	C9—C10—C11—C12	177.70 (10)
N1—C1—C2—C3	179.51 (10)	C10—C11—C12—C13	1.45 (17)
O1—C1—C2—C7	179.10 (10)	C11—C12—C13—O3	177.89 (9)
N1—C1—C2—C7	−0.17 (11)	C11—C12—C13—C14	−1.53 (16)
C7—C2—C3—C4	−0.16 (15)	O3—C13—C14—C15	−179.04 (10)
C1—C2—C3—C4	−179.80 (10)	C12—C13—C14—C15	0.44 (17)
C2—C3—C4—C5	−0.22 (15)	C13—C14—C15—C10	0.78 (17)
C3—C4—C5—C6	0.56 (17)	C11—C10—C15—C14	−0.87 (16)
C4—C5—C6—C7	−0.48 (16)	C9—C10—C15—C14	−178.86 (10)
C5—C6—C7—C2	0.09 (16)	O1—C1—N1—C8	−179.86 (10)
C5—C6—C7—C8	179.06 (10)	C2—C1—N1—C8	−0.56 (11)
C3—C2—C7—C6	0.23 (16)	O1—C1—N1—C9	5.55 (16)
C1—C2—C7—C6	179.94 (9)	C2—C1—N1—C9	−175.15 (9)
C3—C2—C7—C8	−178.94 (9)	O2—C8—N1—C1	−178.80 (10)
C1—C2—C7—C8	0.77 (11)	C7—C8—N1—C1	1.01 (11)
C6—C7—C8—O2	−0.35 (19)	O2—C8—N1—C9	−4.19 (16)
C2—C7—C8—O2	178.72 (10)	C7—C8—N1—C9	175.62 (9)
C6—C7—C8—N1	179.84 (10)	C10—C9—N1—C1	91.16 (12)
C2—C7—C8—N1	−1.09 (11)	C10—C9—N1—C8	−82.81 (13)
N1—C9—C10—C11	−82.66 (14)	C14—C13—O3—C16	−170.86 (10)
N1—C9—C10—C15	95.28 (13)	C12—C13—O3—C16	9.69 (15)
C15—C10—C11—C12	−0.26 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H3···O1i	0.959 (14)	2.422 (14)	3.245 (2)	143.7 (10)
C16—H13···O2ii	0.98	2.53	3.287 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H3⋯O1i	0.959 (14)	2.422 (14)	3.245 (2)	143.7 (10)
C16—H13⋯O2ii	0.98	2.53	3.287 (2)	134

Symmetry codes: (i) ; (ii) .