A new polymorph of N-phenyl-phthalimide.

During an attempt to prepare a cocrystal of N-phenyl-phthalimide, C(14)H(9)NO(2), with N-(2,3,4,5,6-penta-fluoro-phen-yl)phthalimide, a new ortho-rhom-bic polymorph of the first component was obtained. This new form has Z' = 0.5 and the mol-ecule is located around a twofold axis, whereas in the previously reported polymorph (space group Pbca), the mol-ecule has no crystallographically imposed symmetry. Pairs of C-H⋯O inter-actions between inversion-related phthalimide units arrange mol-ecules into tapes that are further assembled into (010) layers via stacking inter-actions between phthalimide fragments [inter-planar distance = 3.37 (5) Å].

Related literature

For the crystal structure of another polymorph of N-phenyl­phthalimide, see: Magomedova et al. (1981 ▶); Schwarzer & Weber (2008 ▶).

Experimental

Crystal data

C14H9NO2

M = 223.22

Orthorhombic,

a = 5.5480 (11) Å

b = 23.801 (5) Å

c = 8.0250 (16) Å

V = 1059.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.2 × 0.05 × 0.05 mm

Data collection

Stoe Stadi-4 diffractometer

Absorption correction: none

1039 measured reflections

1039 independent reflections

662 reflections with I > 2σ(I)

3 standard reflections every 60 reflections intensity decay: 3.9%

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.137

S = 1.17

1039 reflections

80 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: STADI4 (Stoe & Cie, 1997 ▶); cell refinement: STADI4; data reduction: X-RED (Stoe &Cie, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006746/gk2189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006746/gk2189Isup2.hkl

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

C14H9NO2	F(000) = 464
Mr = 223.22	Dx = 1.399 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 25 reflections
a = 5.5480 (11) Å	θ = 10–25°
b = 23.801 (5) Å	µ = 0.10 mm−1
c = 8.0250 (16) Å	T = 293 K
V = 1059.7 (4) Å3	Needle, colourless
Z = 4	0.2 × 0.05 × 0.05 mm

Stoe Stadi-4 diffractometer	Rint = 0.0000
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 1.7°
graphite	h = 0→6
ω–2τ scans	k = −29→0
1039 measured reflections	l = 0→9
1039 independent reflections	3 standard reflections every 60 reflections
662 reflections with I > 2σ(I)	intensity decay: 3.9%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0266P)2 + 0.8879P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max < 0.001
1039 reflections	Δρmax = 0.17 e Å−3
80 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0123 (18)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.0000	0.39051 (14)	0.2500	0.0475 (9)
O1	0.3444 (4)	0.40588 (9)	0.0909 (3)	0.0624 (7)
C1	0.1048 (7)	0.58237 (14)	0.2026 (4)	0.0740 (12)
H1	0.1731	0.6164	0.1709	0.089*
C2	0.2140 (6)	0.53244 (14)	0.1544 (4)	0.0626 (10)
H2	0.3548	0.5324	0.0916	0.075*
C3	0.1056 (5)	0.48304 (12)	0.2034 (3)	0.0491 (8)
C4	0.1752 (6)	0.42378 (12)	0.1702 (4)	0.0479 (8)
C5	0.0000	0.33042 (18)	0.2500	0.0498 (11)
C6	0.1868 (6)	0.30175 (13)	0.3253 (4)	0.0601 (9)
H6	0.3125	0.3213	0.3754	0.072*
C7	0.1855 (6)	0.24375 (14)	0.3257 (5)	0.0765 (12)
H7	0.3099	0.2241	0.3771	0.092*
C8	0.0000	0.2150 (2)	0.2500	0.0820 (19)
H8	0.0000	0.1759	0.2500	0.098*

	U11	U22	U33	U12	U13	U23
N1	0.044 (2)	0.049 (2)	0.049 (2)	0.000	0.0052 (18)	0.000
O1	0.0502 (13)	0.0738 (15)	0.0631 (15)	0.0017 (12)	0.0078 (12)	0.0049 (12)
C1	0.088 (3)	0.0545 (19)	0.079 (3)	−0.0123 (18)	−0.033 (2)	0.0080 (18)
C2	0.063 (2)	0.066 (2)	0.059 (2)	−0.0128 (18)	−0.0198 (18)	0.0059 (18)
C3	0.0502 (17)	0.0543 (18)	0.0427 (18)	−0.0033 (14)	−0.0134 (15)	0.0018 (14)
C4	0.0409 (16)	0.0589 (19)	0.0438 (17)	−0.0017 (16)	−0.0061 (15)	0.0036 (15)
C5	0.048 (2)	0.050 (3)	0.052 (3)	0.000	0.003 (2)	0.000
C6	0.0476 (18)	0.062 (2)	0.070 (2)	0.0027 (17)	−0.0001 (18)	0.0049 (18)
C7	0.057 (2)	0.067 (2)	0.106 (3)	0.013 (2)	0.011 (2)	0.018 (2)
C8	0.058 (3)	0.057 (3)	0.130 (5)	0.000	0.033 (4)	0.000

N1—C4i	1.408 (3)	C3—C4	1.487 (4)
N1—C4	1.408 (3)	C5—C6	1.380 (4)
N1—C5	1.430 (5)	C5—C6i	1.380 (4)
O1—C4	1.211 (3)	C6—C7	1.380 (4)
C1—C2	1.389 (4)	C6—H6	0.9300
C1—C1i	1.389 (8)	C7—C8	1.378 (4)
C1—H1	0.9300	C7—H7	0.9300
C2—C3	1.378 (4)	C8—C7i	1.378 (4)
C2—H2	0.9300	C8—H8	0.9300
C3—C3i	1.389 (6)
C4i—N1—C4	111.6 (4)	N1—C4—C3	105.8 (3)
C4i—N1—C5	124.22 (18)	C6—C5—C6i	120.7 (4)
C4—N1—C5	124.22 (18)	C6—C5—N1	119.6 (2)
C2—C1—C1i	121.2 (2)	C6i—C5—N1	119.6 (2)
C2—C1—H1	119.4	C7—C6—C5	119.5 (4)
C1i—C1—H1	119.4	C7—C6—H6	120.3
C3—C2—C1	117.4 (3)	C5—C6—H6	120.3
C3—C2—H2	121.3	C8—C7—C6	120.0 (4)
C1—C2—H2	121.3	C8—C7—H7	120.0
C2—C3—C3i	121.4 (2)	C6—C7—H7	120.0
C2—C3—C4	130.2 (3)	C7—C8—C7i	120.3 (5)
C3i—C3—C4	108.40 (16)	C7—C8—H8	119.8
O1—C4—N1	125.2 (3)	C7i—C8—H8	119.8
O1—C4—C3	129.0 (3)