Crystal structure of (5-chloro-2-hy-droxy-phen-yl)(3-methyl-isoxazolo[5,4-b]pyridin-5-yl)methanone.

In the title compound, C14H9ClN2O3, the fused pyridine and isoxazole rings are approximately planar, making a dihedral angle of 1.14 (16)°. The mol-ecule is twisted with the benzene ring and the mean plane through the fused pyridine-isoxazole ring system being inclined to one another by 47.03 (13)°. There is an intra-molecular O-H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯N hydrogen bonds, forming chains propagating along [001]. The chains are linked by slipped parallel π-π inter-actions, involving inversion-related benzene rings, forming slabs lying parallel to the bc plane {inter-centroid distance = 3.770 (2) Å].

Related literature

For various applications of polyfunctional pyridines, see: Knyazhanskii et al. (1996 ▸); Kürfurst et al. (1989 ▸); Enyedy et al. (2003 ▸); Arora & Knaus (1999 ▸); Kim et al. 2004 ▸); Pillai et al.(2003 ▸).

Experimental

Crystal data

C14H9ClN2O3

M = 288.68

Monoclinic,

a = 11.0317 (10) Å

b = 11.8701 (10) Å

c = 11.1220 (9) Å

β = 118.675 (2)°

V = 1277.78 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.900, T max = 0.927

17705 measured reflections

2250 independent reflections

1763 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.110

S = 1.13

2250 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015019635/su5220sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015019635/su5220Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015019635/su5220Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015019635/su5220fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

b- . DOI: 10.1107/S2056989015019635/su5220fig2.tif

A view along the b-axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1431889

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H9ClN2O3	F(000) = 592
Mr = 288.68	Dx = 1.501 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1763 reflections
a = 11.0317 (10) Å	θ = 2.1–25.0°
b = 11.8701 (10) Å	µ = 0.31 mm−1
c = 11.1220 (9) Å	T = 293 K
β = 118.675 (2)°	Block, colourless
V = 1277.78 (19) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	2250 independent reflections
Radiation source: fine-focus sealed tube	1763 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω and φ scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.900, Tmax = 0.927	k = −14→14
17705 measured reflections	l = −13→13

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0188P)2 + 1.3834P] where P = (Fo2 + 2Fc2)/3
2250 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.42 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	0.1833 (3)	−0.0368 (3)	0.9816 (3)	0.0592 (8)
C2	0.1378 (3)	0.0264 (4)	0.8629 (3)	0.0738 (10)
H2	0.1386	−0.0051	0.7868	0.089*
C3	0.0917 (3)	0.1343 (3)	0.8560 (3)	0.0711 (10)
H3	0.0614	0.1755	0.7755	0.085*
C4	0.0900 (3)	0.1827 (3)	0.9696 (3)	0.0541 (7)
C5	0.1386 (2)	0.1234 (2)	1.0890 (2)	0.0432 (6)
H5	0.1384	0.1564	1.1648	0.052*
C6	0.1887 (2)	0.0133 (2)	1.0988 (3)	0.0436 (6)
C7	0.2418 (2)	−0.0531 (2)	1.2263 (3)	0.0455 (6)
C8	0.2796 (2)	−0.0001 (2)	1.3606 (3)	0.0424 (6)
C9	0.2544 (3)	−0.0637 (2)	1.4535 (3)	0.0578 (7)
H9	0.2125	−0.1336	1.4243	0.069*
C10	0.3469 (3)	0.0675 (3)	1.6116 (3)	0.0528 (7)
C11	0.3811 (2)	0.1373 (2)	1.5332 (2)	0.0414 (6)
C12	0.3455 (2)	0.1025 (2)	1.4011 (2)	0.0388 (6)
H12	0.3652	0.1460	1.3430	0.047*
C13	0.4447 (3)	0.2330 (2)	1.6185 (2)	0.0471 (6)
C14	0.5010 (3)	0.3350 (3)	1.5876 (3)	0.0607 (8)
H14A	0.5386	0.3840	1.6659	0.091*
H14B	0.4286	0.3733	1.5107	0.091*
H14C	0.5726	0.3140	1.5662	0.091*
N1	0.2861 (3)	−0.0312 (2)	1.5798 (3)	0.0656 (7)
N2	0.4480 (3)	0.2213 (2)	1.7365 (2)	0.0640 (7)
O1	0.2205 (3)	−0.1444 (2)	0.9793 (3)	0.0850 (8)
H1	0.2460	−0.1732	1.0547	0.127*
O2	0.2567 (2)	−0.15626 (16)	1.2243 (2)	0.0661 (6)
O3	0.3854 (2)	0.1149 (2)	1.73518 (19)	0.0709 (6)
Cl1	0.02472 (9)	0.31717 (7)	0.95930 (9)	0.0802 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0495 (17)	0.074 (2)	0.0569 (18)	−0.0167 (15)	0.0281 (14)	−0.0221 (16)
C2	0.071 (2)	0.106 (3)	0.0519 (19)	−0.033 (2)	0.0359 (17)	−0.0268 (19)
C3	0.061 (2)	0.102 (3)	0.0392 (16)	−0.0353 (19)	0.0150 (14)	0.0022 (17)
C4	0.0383 (14)	0.0663 (18)	0.0424 (15)	−0.0144 (13)	0.0070 (12)	0.0058 (13)
C5	0.0346 (13)	0.0518 (15)	0.0355 (13)	−0.0093 (11)	0.0106 (11)	−0.0045 (11)
C6	0.0340 (13)	0.0525 (15)	0.0442 (14)	−0.0113 (11)	0.0188 (11)	−0.0120 (12)
C7	0.0335 (13)	0.0425 (15)	0.0556 (16)	0.0001 (11)	0.0175 (12)	−0.0020 (12)
C8	0.0371 (13)	0.0408 (14)	0.0444 (14)	0.0072 (11)	0.0156 (11)	0.0055 (11)
C9	0.0558 (17)	0.0484 (16)	0.0618 (18)	0.0011 (13)	0.0222 (15)	0.0138 (14)
C10	0.0456 (16)	0.073 (2)	0.0380 (14)	0.0126 (14)	0.0183 (12)	0.0119 (14)
C11	0.0364 (13)	0.0506 (15)	0.0355 (13)	0.0095 (11)	0.0159 (11)	0.0066 (11)
C12	0.0336 (12)	0.0447 (14)	0.0365 (12)	0.0059 (11)	0.0154 (10)	0.0061 (11)
C13	0.0381 (14)	0.0623 (17)	0.0339 (13)	0.0125 (12)	0.0116 (11)	−0.0022 (12)
C14	0.0591 (18)	0.0647 (19)	0.0491 (16)	−0.0026 (15)	0.0185 (14)	−0.0124 (14)
N1	0.0707 (17)	0.0709 (18)	0.0530 (15)	0.0019 (14)	0.0277 (13)	0.0197 (13)
N2	0.0630 (16)	0.088 (2)	0.0388 (13)	0.0124 (14)	0.0224 (12)	−0.0035 (13)
O1	0.0909 (17)	0.0841 (17)	0.0906 (17)	−0.0042 (14)	0.0521 (15)	−0.0375 (14)
O2	0.0642 (13)	0.0443 (12)	0.0777 (15)	0.0077 (10)	0.0243 (11)	−0.0065 (10)
O3	0.0781 (15)	0.0984 (18)	0.0404 (11)	0.0073 (13)	0.0317 (11)	0.0092 (11)
Cl1	0.0684 (5)	0.0677 (5)	0.0732 (6)	−0.0036 (4)	0.0090 (4)	0.0258 (4)

C1—O1	1.345 (4)	C9—N1	1.331 (4)
C1—C2	1.386 (5)	C9—H9	0.9300
C1—C6	1.408 (4)	C10—N1	1.312 (4)
C2—C3	1.366 (5)	C10—O3	1.351 (3)
C2—H2	0.9300	C10—C11	1.380 (4)
C3—C4	1.396 (4)	C11—C12	1.390 (3)
C3—H3	0.9300	C11—C13	1.430 (4)
C4—C5	1.365 (4)	C12—H12	0.9300
C4—Cl1	1.733 (3)	C13—N2	1.302 (3)
C5—C6	1.403 (4)	C13—C14	1.474 (4)
C5—H5	0.9300	C14—H14A	0.9600
C6—C7	1.476 (4)	C14—H14B	0.9600
C7—O2	1.237 (3)	C14—H14C	0.9600
C7—C8	1.485 (4)	N2—O3	1.436 (3)
C8—C12	1.378 (3)	O1—H1	0.8200
C8—C9	1.411 (4)
O1—C1—C2	118.0 (3)	N1—C9—H9	117.5
O1—C1—C6	122.8 (3)	C8—C9—H9	117.5
C2—C1—C6	119.2 (3)	N1—C10—O3	121.1 (3)
C3—C2—C1	121.1 (3)	N1—C10—C11	128.7 (3)
C3—C2—H2	119.5	O3—C10—C11	110.2 (3)
C1—C2—H2	119.5	C10—C11—C12	117.7 (3)
C2—C3—C4	120.1 (3)	C10—C11—C13	104.7 (2)
C2—C3—H3	120.0	C12—C11—C13	137.5 (2)
C4—C3—H3	120.0	C8—C12—C11	116.4 (2)
C5—C4—C3	120.0 (3)	C8—C12—H12	121.8
C5—C4—Cl1	119.7 (2)	C11—C12—H12	121.8
C3—C4—Cl1	120.4 (2)	N2—C13—C11	110.5 (3)
C4—C5—C6	120.8 (3)	N2—C13—C14	120.7 (3)
C4—C5—H5	119.6	C11—C13—C14	128.7 (2)
C6—C5—H5	119.6	C13—C14—H14A	109.5
C5—C6—C1	118.8 (3)	C13—C14—H14B	109.5
C5—C6—C7	122.2 (2)	H14A—C14—H14B	109.5
C1—C6—C7	119.0 (3)	C13—C14—H14C	109.5
O2—C7—C6	120.4 (2)	H14A—C14—H14C	109.5
O2—C7—C8	117.6 (2)	H14B—C14—H14C	109.5
C6—C7—C8	122.0 (2)	C10—N1—C9	112.6 (2)
C12—C8—C9	119.5 (2)	C13—N2—O3	107.7 (2)
C12—C8—C7	123.5 (2)	C1—O1—H1	109.5
C9—C8—C7	116.8 (2)	C10—O3—N2	106.9 (2)
N1—C9—C8	125.0 (3)
O1—C1—C2—C3	176.6 (3)	C7—C8—C9—N1	177.5 (3)
C6—C1—C2—C3	−3.4 (5)	N1—C10—C11—C12	1.4 (4)
C1—C2—C3—C4	0.1 (5)	O3—C10—C11—C12	−178.4 (2)
C2—C3—C4—C5	2.1 (4)	N1—C10—C11—C13	179.9 (3)
C2—C3—C4—Cl1	−177.2 (2)	O3—C10—C11—C13	0.1 (3)
C3—C4—C5—C6	−0.9 (4)	C9—C8—C12—C11	−1.1 (3)
Cl1—C4—C5—C6	178.34 (18)	C7—C8—C12—C11	−176.2 (2)
C4—C5—C6—C1	−2.4 (4)	C10—C11—C12—C8	−0.4 (3)
C4—C5—C6—C7	−180.0 (2)	C13—C11—C12—C8	−178.3 (3)
O1—C1—C6—C5	−175.5 (2)	C10—C11—C13—N2	0.0 (3)
C2—C1—C6—C5	4.4 (4)	C12—C11—C13—N2	178.0 (3)
O1—C1—C6—C7	2.2 (4)	C10—C11—C13—C14	−179.6 (3)
C2—C1—C6—C7	−177.9 (3)	C12—C11—C13—C14	−1.6 (5)
C5—C6—C7—O2	164.1 (2)	O3—C10—N1—C9	179.3 (3)
C1—C6—C7—O2	−13.5 (4)	C11—C10—N1—C9	−0.6 (4)
C5—C6—C7—C8	−16.1 (4)	C8—C9—N1—C10	−1.2 (4)
C1—C6—C7—C8	166.3 (2)	C11—C13—N2—O3	0.0 (3)
O2—C7—C8—C12	140.6 (3)	C14—C13—N2—O3	179.6 (2)
C6—C7—C8—C12	−39.3 (4)	N1—C10—O3—N2	−179.9 (2)
O2—C7—C8—C9	−34.7 (3)	C11—C10—O3—N2	−0.1 (3)
C6—C7—C8—C9	145.5 (2)	C13—N2—O3—C10	0.0 (3)
C12—C8—C9—N1	2.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.84	2.561 (4)	145
C12—H12···N2i	0.93	2.40	3.315 (4)	168

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1O2	0.82	1.84	2.561(4)	145
C12H12N2i	0.93	2.40	3.315(4)	168

Symmetry code: (i) .