3-(Pyridin-2-yl)coumarin.

In the title compound, C(14)H(9)NO(2), the dihedral angle between the pyridine ring and the lactone ring is 10.40 (3)°. The coumarin ring system is nearly planar, with a dihedral angle of 1.40 (2)° between the lactone and benzene rings. An intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, inversion dimers linked by pairs of C-H⋯O inter-actions occur, generating R(2) (2)(14) loops.

Related literature

For background to the structures and properties of coumarins, see: Fylaktakidou et al. (2004 ▶); Griffiths et al. (1995 ▶); Moffett (1964 ▶); Ren & Huo (2008 ▶); Ren et al. (2010 ▶); Trenor et al. (2004 ▶); Walshe et al. (1997 ▶); Yu et al. (2006 ▶); Yu, Yang et al. (2010 ▶); Yu, Zhang et al. (2010 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H9NO2

M = 223.22

Orthorhombic,

a = 7.1107 (3) Å

b = 13.9635 (5) Å

c = 21.2867 (9) Å

V = 2113.56 (15) Å3

Z = 8

Cu Kα radiation

μ = 0.77 mm−1

T = 293 K

0.31 × 0.22 × 0.11 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.795, T max = 0.920

4495 measured reflections

2055 independent reflections

1581 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.230

S = 1.09

2055 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039796/hb5667sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039796/hb5667Isup2.hkl

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

C14H9NO2	Dx = 1.403 Mg m−3
Mr = 223.22	Melting point = 416–417 K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54184 Å
a = 7.1107 (3) Å	Cell parameters from 4495 reflections
b = 13.9635 (5) Å	θ = 4.2–72.5°
c = 21.2867 (9) Å	µ = 0.77 mm−1
V = 2113.56 (15) Å3	T = 293 K
Z = 8	Block, colourless
F(000) = 928	0.31 × 0.22 × 0.11 mm

Siemens SMART CCD diffractometer	2055 independent reflections
Radiation source: fine-focus sealed tube	1581 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 72.5°, θmin = 4.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→8
Tmin = 0.795, Tmax = 0.920	k = −15→17
4495 measured reflections	l = −16→26

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.230	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1725P)2] where P = (Fo2 + 2Fc2)/3
2055 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.43 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	0.2429 (4)	0.14529 (15)	0.41263 (10)	0.0430 (6)
C2	0.3906 (4)	0.20503 (18)	0.42654 (12)	0.0544 (7)
H2	0.3935	0.2381	0.4645	0.065*
C3	0.5343 (4)	0.21543 (19)	0.38377 (14)	0.0596 (7)
H3	0.6346	0.2559	0.3928	0.072*
C4	0.5307 (4)	0.1655 (2)	0.32686 (13)	0.0577 (7)
H4	0.6279	0.1730	0.2980	0.069*
C5	0.3826 (4)	0.10503 (18)	0.31356 (11)	0.0505 (6)
H5	0.3811	0.0716	0.2758	0.061*
C6	0.2348 (3)	0.09346 (15)	0.35618 (10)	0.0408 (5)
C7	0.0765 (3)	0.03304 (15)	0.34618 (9)	0.0410 (5)
H7	0.0717	−0.0030	0.3095	0.049*
C8	−0.0669 (3)	0.02542 (14)	0.38726 (9)	0.0393 (5)
C9	−0.0573 (4)	0.08126 (16)	0.44606 (10)	0.0448 (6)
C10	−0.2310 (3)	−0.03764 (15)	0.37410 (9)	0.0396 (5)
C11	−0.3687 (4)	−0.06205 (18)	0.41772 (11)	0.0497 (6)
H11	−0.3634	−0.0377	0.4583	0.060*
C12	−0.5124 (4)	−0.1222 (2)	0.40050 (12)	0.0562 (7)
H12	−0.6053	−0.1386	0.4293	0.067*
C13	−0.5179 (4)	−0.15823 (19)	0.34010 (12)	0.0541 (6)
H13	−0.6128	−0.1997	0.3273	0.065*
C14	−0.3768 (4)	−0.13020 (18)	0.29945 (11)	0.0507 (6)
H14	−0.3802	−0.1538	0.2586	0.061*
N1	−0.2370 (3)	−0.07198 (14)	0.31462 (8)	0.0462 (5)
O1	0.0984 (3)	0.13797 (12)	0.45491 (8)	0.0503 (5)
O2	−0.1716 (3)	0.08250 (16)	0.48780 (9)	0.0668 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0534 (12)	0.0348 (10)	0.0408 (11)	0.0064 (9)	−0.0047 (9)	−0.0012 (8)
C2	0.0652 (15)	0.0419 (11)	0.0562 (13)	0.0006 (11)	−0.0111 (11)	−0.0058 (9)
C3	0.0567 (14)	0.0453 (12)	0.0768 (16)	−0.0083 (11)	−0.0103 (13)	0.0041 (11)
C4	0.0518 (13)	0.0560 (14)	0.0652 (15)	−0.0017 (12)	0.0045 (12)	0.0062 (11)
C5	0.0541 (13)	0.0494 (12)	0.0479 (12)	0.0035 (10)	0.0039 (10)	−0.0010 (9)
C6	0.0469 (12)	0.0361 (10)	0.0394 (10)	0.0070 (8)	−0.0045 (8)	−0.0012 (8)
C7	0.0508 (12)	0.0398 (10)	0.0324 (10)	0.0056 (9)	−0.0016 (8)	−0.0047 (7)
C8	0.0490 (12)	0.0364 (9)	0.0325 (9)	0.0065 (8)	−0.0011 (8)	−0.0021 (8)
C9	0.0533 (13)	0.0439 (11)	0.0372 (10)	0.0057 (10)	0.0034 (9)	−0.0063 (8)
C10	0.0483 (12)	0.0365 (10)	0.0341 (10)	0.0059 (8)	−0.0010 (8)	0.0021 (7)
C11	0.0586 (14)	0.0499 (12)	0.0406 (11)	0.0023 (11)	0.0081 (10)	−0.0003 (9)
C12	0.0564 (14)	0.0587 (14)	0.0535 (13)	−0.0035 (12)	0.0129 (11)	0.0070 (10)
C13	0.0563 (14)	0.0494 (12)	0.0566 (13)	−0.0093 (11)	−0.0074 (11)	0.0059 (10)
C14	0.0626 (15)	0.0479 (12)	0.0416 (11)	−0.0051 (10)	−0.0051 (10)	−0.0017 (9)
N1	0.0555 (11)	0.0474 (10)	0.0357 (9)	−0.0036 (8)	0.0007 (8)	−0.0011 (7)
O1	0.0630 (11)	0.0465 (9)	0.0415 (8)	−0.0009 (7)	0.0000 (7)	−0.0119 (6)
O2	0.0746 (13)	0.0742 (13)	0.0514 (10)	−0.0078 (11)	0.0216 (9)	−0.0240 (8)

C1—O1	1.369 (3)	C8—C9	1.476 (3)
C1—C2	1.374 (4)	C8—C10	1.489 (3)
C1—C6	1.404 (3)	C9—O2	1.204 (3)
C2—C3	1.376 (4)	C9—O1	1.375 (3)
C2—H2	0.9300	C10—N1	1.355 (3)
C3—C4	1.398 (4)	C10—C11	1.392 (3)
C3—H3	0.9300	C11—C12	1.373 (4)
C4—C5	1.379 (4)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.381 (4)
C5—C6	1.398 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—C14	1.382 (4)
C6—C7	1.423 (3)	C13—H13	0.9300
C7—C8	1.347 (3)	C14—N1	1.324 (3)
C7—H7	0.9300	C14—H14	0.9300
O1—C1—C2	118.5 (2)	C7—C8—C10	121.18 (18)
O1—C1—C6	119.5 (2)	C9—C8—C10	120.52 (19)
C2—C1—C6	121.9 (2)	O2—C9—O1	115.7 (2)
C1—C2—C3	119.3 (2)	O2—C9—C8	127.0 (2)
C1—C2—H2	120.4	O1—C9—C8	117.2 (2)
C3—C2—H2	120.4	N1—C10—C11	121.0 (2)
C2—C3—C4	120.5 (2)	N1—C10—C8	114.20 (19)
C2—C3—H3	119.8	C11—C10—C8	124.82 (19)
C4—C3—H3	119.8	C12—C11—C10	119.7 (2)
C5—C4—C3	119.8 (3)	C12—C11—H11	120.2
C5—C4—H4	120.1	C10—C11—H11	120.2
C3—C4—H4	120.1	C11—C12—C13	119.5 (2)
C4—C5—C6	120.8 (2)	C11—C12—H12	120.2
C4—C5—H5	119.6	C13—C12—H12	120.2
C6—C5—H5	119.6	C12—C13—C14	117.4 (2)
C5—C6—C1	117.7 (2)	C12—C13—H13	121.3
C5—C6—C7	124.5 (2)	C14—C13—H13	121.3
C1—C6—C7	117.8 (2)	N1—C14—C13	124.5 (2)
C8—C7—C6	123.25 (19)	N1—C14—H14	117.8
C8—C7—H7	118.4	C13—C14—H14	117.8
C6—C7—H7	118.4	C14—N1—C10	118.0 (2)
C7—C8—C9	118.3 (2)	C1—O1—C9	123.88 (17)
O1—C1—C2—C3	−178.1 (2)	C10—C8—C9—O1	−179.93 (19)
C6—C1—C2—C3	0.7 (4)	C7—C8—C10—N1	−10.5 (3)
C1—C2—C3—C4	−0.3 (4)	C9—C8—C10—N1	169.58 (19)
C2—C3—C4—C5	−0.3 (4)	C7—C8—C10—C11	168.8 (2)
C3—C4—C5—C6	0.5 (4)	C9—C8—C10—C11	−11.1 (3)
C4—C5—C6—C1	−0.1 (3)	N1—C10—C11—C12	0.4 (4)
C4—C5—C6—C7	179.7 (2)	C8—C10—C11—C12	−178.9 (2)
O1—C1—C6—C5	178.3 (2)	C10—C11—C12—C13	0.3 (4)
C2—C1—C6—C5	−0.5 (3)	C11—C12—C13—C14	−0.7 (4)
O1—C1—C6—C7	−1.6 (3)	C12—C13—C14—N1	0.4 (4)
C2—C1—C6—C7	179.7 (2)	C13—C14—N1—C10	0.2 (4)
C5—C6—C7—C8	−177.9 (2)	C11—C10—N1—C14	−0.7 (3)
C1—C6—C7—C8	1.8 (3)	C8—C10—N1—C14	178.7 (2)
C6—C7—C8—C9	−1.1 (3)	C2—C1—O1—C9	179.5 (2)
C6—C7—C8—C10	178.96 (18)	C6—C1—O1—C9	0.7 (3)
C7—C8—C9—O2	−179.5 (3)	O2—C9—O1—C1	179.8 (2)
C10—C8—C9—O2	0.4 (4)	C8—C9—O1—C1	0.1 (3)
C7—C8—C9—O1	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2	0.93	2.25	2.875 (3)	124
C12—H12···O2i	0.93	2.50	3.318 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2	0.93	2.25	2.875 (3)	124
C12—H12⋯O2i	0.93	2.50	3.318 (3)	147

Symmetry code: (i) .