N-(2-Pheneth­yl)phthalimide

The mol­ecule of the title compound, C₁₆H₁₃NO₂, contains two planar units, viz. a phthalimide system and a phenyl ring in almost parallel orientation, linked by an ethyl­ene bridge. In the crystal structure, the mol­ecules form centrosymmetric pairs which are held together by π–π inter­actions between the phthalimide systems. The latter are stacked in a head-to-tail fashion with an inter­planar distance of 3.263 (6) Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.095
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.089
            Value of mu given      =     0.090
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C16 H13 N O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SCHAKAL99 (Keller, 1999); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and enCIFer (Allen et al., 2004).

2-phenethylisoindoline-1,3-dione

Crystal data

C16H13NO2	Dx = 1.342 Mg m^−3
Mr = 251.27	Melting point: 401 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 10877 reflections
a = 28.3243 (9) Å	θ = 2.3–27.0°
b = 11.4545 (3) Å	µ = 0.09 mm^−1
c = 7.6680 (2) Å	T = 100 K
V = 2487.81 (12) Å^3	Cube cut from a thick platelet, colourless
Z = 8	0.42 × 0.40 × 0.40 mm
F(000) = 1056

Data collection

Nonius KappaCCD diffractometer	1790 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
Graphite monochromator	θmax = 27.0°, θmin = 2.3°
φ/ω Scans scans	h = −36→27
10877 measured reflections	k = −14→12
2700 independent reflections	l = −9→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0441P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.019
2700 reflections	Δρmax = 0.21 e Å^−3
225 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (8)

Special details

Experimental. for X-ray diffraction, a cubical piece was cut from a thick platelet IR (neat): 1707, 1429, 1396, 1360, 1102, 1069, 991, 870, 756, 721, 709, 700 cm^-1.

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.

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

	x	y	z	Uiso*/Ueq
C1	0.56767 (5)	0.99021 (13)	−0.22494 (18)	0.0199 (4)
C2	0.56150 (5)	0.82365 (13)	−0.05709 (19)	0.0212 (4)
C3	0.51349 (5)	0.85514 (13)	−0.11879 (18)	0.0189 (3)
C4	0.47047 (6)	0.80330 (14)	−0.0875 (2)	0.0236 (4)
C5	0.43074 (6)	0.85466 (14)	−0.1621 (2)	0.0257 (4)
C6	0.43457 (6)	0.95494 (14)	−0.2624 (2)	0.0248 (4)
C7	0.47807 (5)	1.00758 (14)	−0.29280 (19)	0.0217 (4)
C8	0.51736 (5)	0.95540 (12)	−0.22009 (17)	0.0183 (3)
C9	0.64172 (5)	0.91659 (15)	−0.08252 (19)	0.0226 (4)
C10	0.67270 (5)	0.86116 (16)	−0.2219 (2)	0.0249 (4)
C11	0.72388 (5)	0.86486 (13)	−0.16927 (18)	0.0203 (4)
C12	0.75271 (5)	0.95909 (13)	−0.21241 (18)	0.0215 (4)
C13	0.79932 (5)	0.96204 (14)	−0.1583 (2)	0.0236 (4)
C14	0.81823 (6)	0.87171 (14)	−0.05967 (19)	0.0234 (4)
C15	0.78974 (6)	0.77761 (14)	−0.01613 (19)	0.0239 (4)
C16	0.74308 (6)	0.77484 (13)	−0.07092 (19)	0.0225 (4)
N1	0.59159 (4)	0.90951 (10)	−0.12183 (14)	0.0192 (3)
O1	0.58628 (4)	1.07163 (9)	−0.29930 (13)	0.0274 (3)
O2	0.57394 (4)	0.74178 (9)	0.03240 (14)	0.0303 (3)
H4	0.4670 (6)	0.7341 (13)	−0.018 (2)	0.031 (5)*
H5	0.3993 (6)	0.8181 (14)	−0.1393 (19)	0.036 (5)*
H6	0.4068 (6)	0.9888 (13)	−0.3110 (19)	0.031 (5)*
H7	0.4802 (5)	1.0784 (13)	−0.3649 (19)	0.026 (4)*
H9A	0.6493 (6)	1.0029 (14)	−0.0714 (19)	0.036 (5)*
H9B	0.6459 (5)	0.8762 (14)	0.030 (2)	0.033 (4)*
H10A	0.6681 (5)	0.9039 (13)	−0.332 (2)	0.035 (5)*
H10B	0.6617 (6)	0.7778 (15)	−0.2343 (19)	0.036 (5)*
H12	0.7401 (5)	1.0236 (12)	−0.2832 (19)	0.026 (4)*
H13	0.8202 (6)	1.0323 (13)	−0.1907 (18)	0.029 (4)*
H14	0.8512 (6)	0.8719 (13)	−0.0199 (18)	0.032 (4)*
H15	0.8022 (5)	0.7113 (14)	0.057 (2)	0.036 (5)*
H16	0.7236 (6)	0.7060 (14)	−0.042 (2)	0.034 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0202 (9)	0.0202 (8)	0.0194 (8)	−0.0004 (7)	0.0019 (6)	−0.0037 (7)
C2	0.0221 (9)	0.0233 (8)	0.0181 (8)	0.0005 (7)	0.0020 (6)	−0.0028 (7)
C3	0.0174 (8)	0.0201 (8)	0.0193 (8)	−0.0012 (7)	0.0014 (6)	−0.0042 (6)
C4	0.0236 (10)	0.0224 (9)	0.0249 (9)	−0.0026 (7)	0.0050 (7)	−0.0023 (7)
C5	0.0182 (9)	0.0280 (10)	0.0309 (9)	−0.0036 (7)	0.0047 (7)	−0.0088 (7)
C6	0.0169 (9)	0.0308 (10)	0.0266 (9)	0.0043 (8)	−0.0023 (7)	−0.0089 (7)
C7	0.0203 (9)	0.0242 (9)	0.0205 (8)	0.0040 (7)	0.0004 (6)	−0.0034 (7)
C8	0.0153 (8)	0.0216 (8)	0.0179 (7)	0.0004 (6)	0.0024 (6)	−0.0051 (6)
C9	0.0155 (9)	0.0281 (10)	0.0241 (8)	0.0009 (7)	−0.0031 (6)	−0.0016 (8)
C10	0.0174 (9)	0.0331 (10)	0.0241 (9)	0.0000 (8)	−0.0024 (7)	−0.0044 (8)
C11	0.0160 (8)	0.0267 (8)	0.0182 (7)	0.0009 (7)	0.0012 (6)	−0.0048 (7)
C12	0.0218 (9)	0.0225 (8)	0.0201 (8)	0.0030 (7)	−0.0003 (6)	−0.0001 (7)
C13	0.0205 (9)	0.0262 (9)	0.0239 (8)	−0.0040 (8)	0.0019 (7)	−0.0029 (7)
C14	0.0141 (9)	0.0327 (9)	0.0233 (8)	0.0010 (7)	−0.0008 (6)	−0.0026 (7)
C15	0.0225 (9)	0.0265 (9)	0.0228 (8)	0.0037 (7)	0.0014 (7)	0.0030 (7)
C16	0.0204 (9)	0.0236 (9)	0.0234 (8)	−0.0019 (7)	0.0030 (6)	−0.0005 (7)
N1	0.0140 (7)	0.0238 (7)	0.0196 (6)	0.0002 (5)	−0.0006 (5)	0.0008 (6)
O1	0.0219 (7)	0.0259 (6)	0.0346 (6)	−0.0017 (5)	0.0046 (5)	0.0064 (5)
O2	0.0286 (7)	0.0302 (7)	0.0320 (6)	0.0016 (5)	−0.0019 (5)	0.0110 (5)

Geometric parameters (Å, º)

C1—O1	1.2137 (16)	C9—C10	1.522 (2)
C1—N1	1.3924 (18)	C9—H9A	1.015 (15)
C1—C8	1.480 (2)	C9—H9B	0.986 (15)
C2—O2	1.2143 (17)	C10—C11	1.505 (2)
C2—N1	1.3928 (18)	C10—H10A	0.984 (15)
C2—C3	1.484 (2)	C10—H10B	1.008 (17)
C3—C4	1.377 (2)	C11—C16	1.389 (2)
C3—C8	1.391 (2)	C11—C12	1.393 (2)
C4—C5	1.393 (2)	C12—C13	1.384 (2)
C4—H4	0.962 (15)	C12—H12	0.984 (15)
C5—C6	1.386 (2)	C13—C14	1.389 (2)
C5—H5	0.999 (16)	C13—H13	1.030 (16)
C6—C7	1.391 (2)	C14—C15	1.387 (2)
C6—H6	0.952 (16)	C14—H14	0.982 (16)
C7—C8	1.381 (2)	C15—C16	1.387 (2)
C7—H7	0.984 (15)	C15—H15	1.009 (17)
C9—N1	1.4536 (18)	C16—H16	0.988 (16)
O1—C1—N1	124.45 (14)	H9A—C9—H9B	111.0 (13)
O1—C1—C8	129.56 (14)	C11—C10—C9	110.80 (12)
N1—C1—C8	105.99 (12)	C11—C10—H10A	110.1 (9)
O2—C2—N1	124.70 (14)	C9—C10—H10A	108.5 (9)
O2—C2—C3	129.31 (14)	C11—C10—H10B	110.4 (9)
N1—C2—C3	105.98 (12)	C9—C10—H10B	106.5 (9)
C4—C3—C8	121.54 (14)	H10A—C10—H10B	110.5 (13)
C4—C3—C2	130.59 (14)	C16—C11—C12	118.34 (14)
C8—C3—C2	107.85 (12)	C16—C11—C10	120.13 (14)
C3—C4—C5	117.48 (15)	C12—C11—C10	121.50 (14)
C3—C4—H4	122.8 (10)	C13—C12—C11	120.45 (15)
C5—C4—H4	119.7 (10)	C13—C12—H12	119.6 (9)
C6—C5—C4	120.97 (15)	C11—C12—H12	119.9 (9)
C6—C5—H5	120.9 (9)	C12—C13—C14	120.85 (15)
C4—C5—H5	118.1 (9)	C12—C13—H13	119.7 (9)
C5—C6—C7	121.41 (15)	C14—C13—H13	119.4 (9)
C5—C6—H6	119.3 (10)	C13—C14—C15	119.04 (15)
C7—C6—H6	119.2 (10)	C13—C14—H14	122.3 (9)
C8—C7—C6	117.28 (15)	C15—C14—H14	118.7 (9)
C8—C7—H7	122.3 (9)	C16—C15—C14	119.94 (15)
C6—C7—H7	120.4 (9)	C16—C15—H15	118.9 (9)
C7—C8—C3	121.30 (14)	C14—C15—H15	121.1 (9)
C7—C8—C1	130.48 (14)	C15—C16—C11	121.38 (15)
C3—C8—C1	108.19 (13)	C15—C16—H16	118.7 (9)
N1—C9—C10	113.22 (12)	C11—C16—H16	119.9 (9)
N1—C9—H9A	106.1 (9)	C1—N1—C2	111.93 (12)
C10—C9—H9A	110.1 (9)	C1—N1—C9	123.78 (12)
N1—C9—H9B	105.9 (9)	C2—N1—C9	124.27 (13)
C10—C9—H9B	110.4 (9)