N-(2-Pyridylmeth-yl)phthalimide.

In the title compound, C(14)H(10)N(2)O(2), the phtalimide and 2-pyridylmethyl units are almost perpendicular, with an inter-planar angle of 85.74 (2)°. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, forming chains running along the b axis. The packing is further stabilized by offset π-π inter-actions between adjacent pyridine rings, with a centroid-centroid distance of 3.855 (2) Å.

Related literature

For general backround to phthalimides, see: Ing & Manske (1926 ▶); Gibson & Bradshaw (1968 ▶); Ishii & Sakaguchi (2004 ▶). For their applications in photochemical synthesis and catalytic and chiral reactions, see: Yoon & Mariano (2001 ▶); Huang et al. (2006 ▶); Rodríguez et al. 2006 ▶. For their biological activity, see: Miyachi et al. (1997 ▶); Vázquez et al. (2005 ▶). For phthalimide derivatives, see: Vamecq et al. (2000 ▶). For analysis of hydrogen-bonding patterns, see: Hunter (1994 ▶); Desiraju (1991 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H10N2O2

M = 238.24

Monoclinic,

a = 11.7734 (18) Å

b = 14.239 (2) Å

c = 7.0698 (11) Å

β = 106.373 (3)°

V = 1137.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.45 × 0.28 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.958, T max = 0.982

7150 measured reflections

1994 independent reflections

1567 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.155

S = 1.20

1994 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus-NT (Bruker, 2001 ▶); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903846X/fl2266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903846X/fl2266Isup2.hkl

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

C14H10N2O2	F(000) = 496
Mr = 238.24	Dx = 1.392 Mg m−3
Monoclinic, P21/c	Melting point: 399 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.7734 (18) Å	Cell parameters from 2665 reflections
b = 14.239 (2) Å	θ = 2.3–26.8°
c = 7.0698 (11) Å	µ = 0.10 mm−1
β = 106.373 (3)°	T = 293 K
V = 1137.1 (3) Å3	Prism, colourless
Z = 4	0.45 × 0.28 × 0.19 mm

Bruker SMART APEX CCD area-detector diffractometer	1994 independent reflections
Radiation source: fine-focus sealed tube	1567 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 8.3 pixels mm-1	θmax = 25.0°, θmin = 1.8°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −16→16
Tmin = 0.958, Tmax = 0.982	l = −8→8
7150 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.0705P)2 + 0.1417P] where P = (Fo2 + 2Fc2)/3
1994 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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
C1	0.8978 (2)	0.03798 (15)	0.1337 (3)	0.0493 (6)
C2	1.01324 (19)	0.07017 (14)	0.2618 (3)	0.0456 (5)
C3	1.1103 (2)	0.01983 (16)	0.3657 (3)	0.0533 (6)
H3	1.1100	−0.0455	0.3665	0.064*
C4	1.2086 (2)	0.07039 (18)	0.4690 (3)	0.0613 (7)
H4	1.2760	0.0384	0.5399	0.074*
C5	1.2088 (2)	0.16764 (17)	0.4691 (3)	0.0612 (6)
H5	1.2761	0.1997	0.5405	0.073*
C6	1.1106 (2)	0.21791 (16)	0.3648 (3)	0.0557 (6)
H6	1.1105	0.2832	0.3646	0.067*
C7	1.01340 (18)	0.16754 (14)	0.2616 (3)	0.0466 (5)
C8	0.8971 (2)	0.19976 (15)	0.1347 (3)	0.0515 (6)
C9	0.7148 (2)	0.11883 (15)	−0.0729 (3)	0.0576 (6)
H9A	0.7048	0.0621	−0.1517	0.069*
H9B	0.7075	0.1718	−0.1617	0.069*
C10	0.61635 (19)	0.12393 (13)	0.0243 (3)	0.0484 (6)
C11	0.6362 (2)	0.13358 (14)	0.2231 (3)	0.0573 (6)
H11	0.7128	0.1380	0.3066	0.069*
C12	0.5388 (3)	0.13668 (17)	0.2973 (4)	0.0705 (7)
H12	0.5489	0.1437	0.4319	0.085*
C13	0.4280 (2)	0.12929 (16)	0.1695 (5)	0.0708 (7)
H13	0.3614	0.1303	0.2156	0.085*
C14	0.4168 (2)	0.12042 (16)	−0.0258 (4)	0.0672 (7)
H14	0.3410	0.1159	−0.1118	0.081*
N1	0.83334 (16)	0.11904 (11)	0.0626 (3)	0.0530 (5)
N2	0.50806 (18)	0.11779 (12)	−0.1016 (3)	0.0610 (6)
O1	0.86171 (15)	−0.04110 (11)	0.0924 (2)	0.0652 (5)
O2	0.85977 (15)	0.27886 (11)	0.0976 (2)	0.0681 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0604 (15)	0.0411 (13)	0.0521 (13)	−0.0013 (10)	0.0249 (11)	0.0003 (10)
C2	0.0532 (13)	0.0419 (12)	0.0483 (12)	0.0033 (10)	0.0251 (10)	0.0040 (9)
C3	0.0655 (16)	0.0427 (12)	0.0571 (13)	0.0090 (11)	0.0260 (12)	0.0072 (10)
C4	0.0564 (15)	0.0678 (17)	0.0592 (14)	0.0082 (12)	0.0154 (12)	0.0116 (12)
C5	0.0554 (15)	0.0658 (17)	0.0603 (14)	−0.0079 (12)	0.0126 (12)	0.0027 (12)
C6	0.0610 (15)	0.0447 (13)	0.0630 (14)	−0.0036 (11)	0.0201 (12)	0.0014 (11)
C7	0.0528 (13)	0.0407 (12)	0.0507 (12)	0.0014 (9)	0.0217 (10)	0.0034 (9)
C8	0.0566 (14)	0.0404 (13)	0.0608 (14)	0.0018 (10)	0.0218 (11)	0.0040 (10)
C9	0.0572 (14)	0.0559 (15)	0.0555 (13)	−0.0027 (11)	0.0088 (11)	0.0002 (10)
C10	0.0528 (13)	0.0335 (12)	0.0540 (12)	0.0012 (9)	0.0069 (10)	0.0016 (9)
C11	0.0575 (14)	0.0506 (14)	0.0571 (13)	−0.0010 (11)	0.0052 (11)	−0.0051 (10)
C12	0.088 (2)	0.0634 (17)	0.0610 (15)	0.0016 (14)	0.0220 (15)	−0.0102 (12)
C13	0.0612 (16)	0.0625 (17)	0.091 (2)	0.0054 (12)	0.0250 (15)	−0.0024 (14)
C14	0.0513 (15)	0.0626 (17)	0.0794 (18)	−0.0002 (11)	0.0050 (13)	0.0013 (13)
N1	0.0516 (11)	0.0409 (11)	0.0647 (12)	−0.0015 (8)	0.0135 (9)	0.0013 (8)
N2	0.0555 (12)	0.0563 (13)	0.0627 (12)	−0.0001 (9)	0.0029 (10)	0.0025 (9)
O1	0.0795 (12)	0.0428 (10)	0.0732 (11)	−0.0070 (8)	0.0214 (9)	−0.0059 (8)
O2	0.0689 (11)	0.0409 (10)	0.0873 (12)	0.0063 (8)	0.0100 (9)	0.0071 (8)

C1—O1	1.210 (3)	C8—N1	1.389 (3)
C1—N1	1.395 (3)	C9—N1	1.453 (3)
C1—C2	1.477 (3)	C9—C10	1.506 (3)
C2—C3	1.374 (3)	C9—H9A	0.9700
C2—C7	1.386 (3)	C9—H9B	0.9700
C3—C4	1.383 (3)	C10—N2	1.336 (3)
C3—H3	0.9300	C10—C11	1.366 (3)
C4—C5	1.385 (4)	C11—C12	1.391 (3)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.382 (3)	C12—C13	1.365 (4)
C5—H5	0.9300	C12—H12	0.9300
C6—C7	1.373 (3)	C13—C14	1.356 (4)
C6—H6	0.9300	C13—H13	0.9300
C7—C8	1.483 (3)	C14—N2	1.329 (3)
C8—O2	1.210 (2)	C14—H14	0.9300
O1—C1—N1	124.4 (2)	N1—C9—H9A	108.6
O1—C1—C2	129.5 (2)	C10—C9—H9A	108.6
N1—C1—C2	106.10 (18)	N1—C9—H9B	108.6
C3—C2—C7	121.4 (2)	C10—C9—H9B	108.6
C3—C2—C1	130.5 (2)	H9A—C9—H9B	107.5
C7—C2—C1	108.13 (18)	N2—C10—C11	123.1 (2)
C2—C3—C4	117.2 (2)	N2—C10—C9	113.95 (19)
C2—C3—H3	121.4	C11—C10—C9	122.9 (2)
C4—C3—H3	121.4	C10—C11—C12	118.1 (2)
C3—C4—C5	121.5 (2)	C10—C11—H11	120.9
C3—C4—H4	119.3	C12—C11—H11	120.9
C5—C4—H4	119.3	C13—C12—C11	118.9 (3)
C6—C5—C4	121.1 (2)	C13—C12—H12	120.5
C6—C5—H5	119.4	C11—C12—H12	120.5
C4—C5—H5	119.4	C14—C13—C12	118.8 (2)
C7—C6—C5	117.3 (2)	C14—C13—H13	120.6
C7—C6—H6	121.3	C12—C13—H13	120.6
C5—C6—H6	121.3	N2—C14—C13	123.8 (2)
C6—C7—C2	121.5 (2)	N2—C14—H14	118.1
C6—C7—C8	130.5 (2)	C13—C14—H14	118.1
C2—C7—C8	107.97 (19)	C8—N1—C1	111.69 (19)
O2—C8—N1	124.4 (2)	C8—N1—C9	124.25 (18)
O2—C8—C7	129.5 (2)	C1—N1—C9	124.06 (18)
N1—C8—C7	106.11 (18)	C14—N2—C10	117.2 (2)
N1—C9—C10	114.79 (19)
O1—C1—C2—C3	0.9 (4)	N1—C9—C10—C11	3.7 (3)
N1—C1—C2—C3	−178.73 (19)	N2—C10—C11—C12	0.3 (3)
O1—C1—C2—C7	179.4 (2)	C9—C10—C11—C12	−179.42 (19)
N1—C1—C2—C7	−0.2 (2)	C10—C11—C12—C13	0.5 (3)
C7—C2—C3—C4	−0.5 (3)	C11—C12—C13—C14	−0.9 (4)
C1—C2—C3—C4	177.91 (19)	C12—C13—C14—N2	0.5 (4)
C2—C3—C4—C5	0.5 (3)	O2—C8—N1—C1	−178.6 (2)
C3—C4—C5—C6	−0.3 (3)	C7—C8—N1—C1	0.7 (2)
C4—C5—C6—C7	0.0 (3)	O2—C8—N1—C9	2.3 (3)
C5—C6—C7—C2	0.1 (3)	C7—C8—N1—C9	−178.38 (18)
C5—C6—C7—C8	−178.8 (2)	O1—C1—N1—C8	−180.0 (2)
C3—C2—C7—C6	0.2 (3)	C2—C1—N1—C8	−0.3 (2)
C1—C2—C7—C6	−178.53 (18)	O1—C1—N1—C9	−0.9 (3)
C3—C2—C7—C8	179.31 (18)	C2—C1—N1—C9	178.74 (18)
C1—C2—C7—C8	0.6 (2)	C10—C9—N1—C8	−87.1 (2)
C6—C7—C8—O2	−2.5 (4)	C10—C9—N1—C1	93.9 (2)
C2—C7—C8—O2	178.4 (2)	C13—C14—N2—C10	0.3 (3)
C6—C7—C8—N1	178.2 (2)	C11—C10—N2—C14	−0.7 (3)
C2—C7—C8—N1	−0.8 (2)	C9—C10—N2—C14	179.06 (18)
N1—C9—C10—N2	−176.06 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.53	3.452 (3)	171
C6—H6···O1ii	0.93	2.53	3.452 (3)	171
C14—H14···O1iii	0.93	2.65	3.373 (3)	135
C11—H11···O2iv	0.93	2.57	3.401 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.53	3.452 (3)	171
C6—H6⋯O1ii	0.93	2.53	3.452 (3)	171
C14—H14⋯O1iii	0.93	2.65	3.373 (3)	135
C11—H11⋯O2iv	0.93	2.57	3.401 (3)	148

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .