1-(3-Chloro-phen-yl)-5-(2,4-di-hydroxy-benzo-yl)pyridin-2(1H)-one.

The chloro-phenyl group of the title compound, C18H12ClNO4, is disordered over two orientations with occupancies of 0.331 (8) and 0.669 (8). An intra-molecular hydrogen bond is formed between a hy-droxy group and the acyclic carbonyl group. In the crystal, molecules are linked into chains along [110] by O-H⋯O and C-H⋯O hydrogen bonds, forming a ladder motif.

Related literature

For similar structures, see: Ravinder et al. (2012 ▶); Sengupta et al. (2012 ▶). For the synthesis, see: Chen et al. (2011 ▶); Kim & Hong (2011 ▶). For the biological activity of similar structures, see: Kim et al. (2010 ▶).

Experimental

Crystal data

C18H12ClNO4

M = 341.74

Triclinic,

a = 6.689 (3) Å

b = 9.009 (4) Å

c = 13.257 (6) Å

α = 87.193 (5)°

β = 87.719 (5)°

γ = 82.674 (5)°

V = 791.0 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.15 × 0.12 × 0.05 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.962, T max = 0.987

3286 measured reflections

2726 independent reflections

1929 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.233

S = 1.00

2726 reflections

236 parameters

48 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009689/fy2085sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009689/fy2085Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009689/fy2085Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009689/fy2085Isup4.cml

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

C18H12ClNO4	F(000) = 352
Mr = 341.74	Dx = 1.435 Mg m−3
Triclinic, P1	Melting point: 391 K
a = 6.689 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.009 (4) Å	Cell parameters from 841 reflections
c = 13.257 (6) Å	θ = 2.3–26.8°
α = 87.193 (5)°	µ = 0.26 mm−1
β = 87.719 (5)°	T = 293 K
γ = 82.674 (5)°	Block, yellow
V = 791.0 (6) Å3	0.15 × 0.12 × 0.05 mm
Z = 2

Bruker SMART CCD diffractometer	2726 independent reflections
Radiation source: fine-focus sealed tube	1929 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −5→7
Tmin = 0.962, Tmax = 0.987	k = −9→10
3286 measured reflections	l = −14→15

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.233	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.1737P)2] where P = (Fo2 + 2Fc2)/3
2726 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.36 e Å−3
48 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	Occ. (<1)
C1	0.5151 (4)	−0.2487 (3)	0.2138 (2)	0.0538 (8)
H1A	0.6295	−0.3083	0.2368	0.065*
C2	0.3295 (4)	−0.3066 (3)	0.2132 (2)	0.0495 (7)
C3	0.1599 (4)	−0.2167 (3)	0.1802 (2)	0.0467 (7)
H3	0.0368	−0.2545	0.1811	0.056*
C4	0.1723 (4)	−0.0708 (3)	0.1460 (2)	0.0437 (6)
C5	0.3569 (4)	−0.0092 (3)	0.1467 (2)	0.0445 (6)
C6	0.5255 (4)	−0.1048 (3)	0.1803 (2)	0.0504 (7)
H6	0.6495	−0.0682	0.1796	0.060*
C7	0.3660 (4)	0.1438 (3)	0.1075 (2)	0.0485 (7)
C8	0.5392 (4)	0.2240 (3)	0.1300 (2)	0.0431 (6)
C9	0.6104 (4)	0.3249 (3)	0.0559 (2)	0.0521 (7)
H9	0.5547	0.3347	−0.0076	0.063*
C10	0.7578 (4)	0.4071 (3)	0.0762 (3)	0.0608 (8)
H10	0.8062	0.4692	0.0253	0.073*
C11	0.8409 (4)	0.4009 (3)	0.1736 (2)	0.0554 (8)
C12	0.6192 (4)	0.2166 (3)	0.2224 (2)	0.0460 (7)
H12	0.5742	0.1514	0.2724	0.055*
C13	0.835 (4)	0.298 (2)	0.348 (2)	0.0602 (8)	0.331 (8)
C14	0.679 (4)	0.326 (2)	0.4232 (19)	0.107 (3)	0.331 (8)
H14	0.5465	0.3577	0.4065	0.128*	0.331 (8)
C15	0.737 (4)	0.302 (2)	0.5263 (17)	0.137 (4)	0.331 (8)
H15	0.6406	0.3212	0.5781	0.164*	0.331 (8)
C16	0.928 (4)	0.254 (3)	0.549 (2)	0.109 (3)	0.331 (8)
H16	0.9665	0.2386	0.6154	0.131*	0.331 (8)
C17	1.065 (4)	0.227 (3)	0.471 (2)	0.0914 (18)	0.331 (8)
C18	1.027 (5)	0.242 (3)	0.364 (3)	0.069 (2)	0.331 (8)
H18	1.1232	0.2171	0.3132	0.083*	0.331 (8)
Cl1	1.3150 (14)	0.1781 (14)	0.4928 (8)	0.1598 (17)	0.331 (8)
C13'	0.8340 (19)	0.2944 (10)	0.3452 (10)	0.0602 (8)	0.669 (8)
C14'	0.7299 (15)	0.3857 (11)	0.4146 (8)	0.107 (3)	0.669 (8)
H14'	0.6124	0.4463	0.3966	0.128*	0.669 (8)
C15'	0.7991 (14)	0.3875 (11)	0.5106 (6)	0.137 (4)	0.669 (8)
H15'	0.7286	0.4493	0.5576	0.164*	0.669 (8)
C16'	0.9725 (17)	0.2980 (12)	0.5372 (8)	0.109 (3)	0.669 (8)
H16'	1.0194	0.2993	0.6022	0.131*	0.669 (8)
C17'	1.077 (2)	0.2068 (13)	0.4678 (10)	0.0914 (18)	0.669 (8)
C18'	1.007 (2)	0.2050 (12)	0.3718 (11)	0.069 (2)	0.669 (8)
H18'	1.0780	0.1432	0.3247	0.083*	0.669 (8)
Cl1'	1.2968 (6)	0.0926 (8)	0.5029 (3)	0.1598 (17)	0.669 (8)
N1	0.7644 (3)	0.3024 (2)	0.24405 (18)	0.0477 (6)
O1	0.3277 (3)	−0.4514 (2)	0.24453 (18)	0.0642 (7)
O2	0.0021 (3)	0.0106 (2)	0.11379 (17)	0.0591 (6)
O3	0.2307 (3)	0.2123 (2)	0.05679 (18)	0.0686 (7)
O4	0.9690 (3)	0.4788 (2)	0.1992 (2)	0.0816 (8)
H2	0.044 (5)	0.096 (4)	0.086 (3)	0.077 (10)*
H1	0.214 (7)	−0.478 (5)	0.227 (3)	0.109 (15)*

	U11	U22	U33	U12	U13	U23
C1	0.0483 (14)	0.0462 (14)	0.070 (2)	−0.0105 (11)	−0.0145 (13)	−0.0106 (13)
C2	0.0561 (16)	0.0472 (14)	0.0490 (18)	−0.0157 (12)	−0.0057 (12)	−0.0132 (11)
C3	0.0451 (14)	0.0543 (15)	0.0458 (17)	−0.0217 (11)	−0.0010 (11)	−0.0129 (11)
C4	0.0410 (13)	0.0532 (14)	0.0398 (16)	−0.0115 (11)	−0.0027 (10)	−0.0150 (11)
C5	0.0444 (14)	0.0506 (14)	0.0420 (16)	−0.0149 (11)	−0.0030 (10)	−0.0123 (11)
C6	0.0419 (13)	0.0519 (15)	0.061 (2)	−0.0145 (11)	−0.0059 (12)	−0.0161 (12)
C7	0.0430 (14)	0.0538 (15)	0.0516 (18)	−0.0132 (11)	−0.0041 (12)	−0.0112 (12)
C8	0.0462 (13)	0.0413 (12)	0.0442 (17)	−0.0117 (10)	−0.0031 (11)	−0.0079 (10)
C9	0.0550 (15)	0.0587 (15)	0.0453 (18)	−0.0167 (12)	−0.0046 (12)	−0.0019 (12)
C10	0.0614 (17)	0.0601 (17)	0.064 (2)	−0.0251 (14)	−0.0006 (14)	0.0066 (14)
C11	0.0520 (15)	0.0448 (14)	0.073 (2)	−0.0189 (12)	−0.0066 (13)	−0.0067 (13)
C12	0.0526 (14)	0.0428 (13)	0.0454 (18)	−0.0160 (11)	−0.0004 (12)	−0.0056 (11)
C13	0.0676 (18)	0.0643 (18)	0.052 (2)	−0.0113 (14)	−0.0134 (14)	−0.0153 (14)
C14	0.121 (7)	0.130 (8)	0.061 (4)	0.033 (6)	−0.024 (4)	−0.036 (5)
C15	0.172 (8)	0.167 (10)	0.062 (5)	0.032 (8)	−0.024 (5)	−0.051 (6)
C16	0.118 (7)	0.148 (8)	0.065 (4)	−0.024 (5)	−0.029 (4)	−0.012 (5)
C17	0.079 (3)	0.124 (4)	0.072 (3)	−0.009 (3)	−0.026 (2)	0.000 (3)
C18	0.066 (3)	0.077 (7)	0.065 (3)	−0.012 (4)	−0.009 (2)	−0.004 (4)
Cl1	0.1116 (14)	0.220 (5)	0.1318 (18)	0.034 (3)	−0.0528 (12)	0.048 (3)
C13'	0.0676 (18)	0.0643 (18)	0.052 (2)	−0.0113 (14)	−0.0134 (14)	−0.0153 (14)
C14'	0.121 (7)	0.130 (8)	0.061 (4)	0.033 (6)	−0.024 (4)	−0.036 (5)
C15'	0.172 (8)	0.167 (10)	0.062 (5)	0.032 (8)	−0.024 (5)	−0.051 (6)
C16'	0.118 (7)	0.148 (8)	0.065 (4)	−0.024 (5)	−0.029 (4)	−0.012 (5)
C17'	0.079 (3)	0.124 (4)	0.072 (3)	−0.009 (3)	−0.026 (2)	0.000 (3)
C18'	0.066 (3)	0.077 (7)	0.065 (3)	−0.012 (4)	−0.009 (2)	−0.004 (4)
Cl1'	0.1116 (14)	0.220 (5)	0.1318 (18)	0.034 (3)	−0.0528 (12)	0.048 (3)
N1	0.0537 (12)	0.0454 (11)	0.0477 (15)	−0.0153 (9)	−0.0103 (10)	−0.0097 (10)
O1	0.0658 (13)	0.0476 (11)	0.0836 (17)	−0.0193 (9)	−0.0186 (11)	−0.0013 (10)
O2	0.0421 (10)	0.0625 (12)	0.0751 (16)	−0.0144 (9)	−0.0131 (9)	0.0011 (10)
O3	0.0598 (13)	0.0624 (12)	0.0871 (18)	−0.0197 (10)	−0.0250 (11)	0.0100 (11)
O4	0.0729 (14)	0.0669 (14)	0.114 (2)	−0.0362 (11)	−0.0279 (13)	−0.0020 (13)

C1—C6	1.359 (4)	C13—C14	1.42 (3)
C1—C2	1.407 (4)	C13—N1	1.47 (3)
C1—H1A	0.9300	C14—C15	1.43 (3)
C2—O1	1.350 (3)	C14—H14	0.9300
C2—C3	1.380 (4)	C15—C16	1.34 (3)
C3—C4	1.381 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.36 (3)
C4—O2	1.346 (3)	C16—H16	0.9300
C4—C5	1.418 (3)	C17—C18	1.45 (3)
C5—C6	1.402 (4)	C17—Cl1	1.71 (3)
C5—C7	1.457 (4)	C18—H18	0.9300
C6—H6	0.9300	C13'—C18'	1.373 (8)
C7—O3	1.232 (3)	C13'—C14'	1.373 (8)
C7—C8	1.489 (3)	C13'—N1	1.432 (13)
C8—C12	1.352 (4)	C14'—C15'	1.373 (8)
C8—C9	1.415 (4)	C14'—H14'	0.9300
C9—C10	1.349 (4)	C15'—C16'	1.373 (8)
C9—H9	0.9300	C15'—H15'	0.9300
C10—C11	1.422 (4)	C16'—C17'	1.373 (8)
C10—H10	0.9300	C16'—H16'	0.9300
C11—O4	1.242 (3)	C17'—C18'	1.373 (8)
C11—N1	1.385 (4)	C17'—Cl1'	1.750 (14)
C12—N1	1.363 (3)	C18'—H18'	0.9300
C12—H12	0.9300	O1—H1	0.87 (5)
C13—C18	1.34 (2)	O2—H2	0.91 (4)
C6—C1—C2	119.3 (3)	C13—C14—H14	121.6
C6—C1—H1A	120.3	C15—C14—H14	121.6
C2—C1—H1A	120.3	C16—C15—C14	120.6 (18)
O1—C2—C3	122.9 (2)	C16—C15—H15	119.7
O1—C2—C1	117.2 (3)	C14—C15—H15	119.7
C3—C2—C1	119.9 (2)	C15—C16—C17	118.1 (16)
C2—C3—C4	120.3 (2)	C15—C16—H16	120.9
C2—C3—H3	119.8	C17—C16—H16	120.9
C4—C3—H3	119.8	C16—C17—C18	127.1 (13)
O2—C4—C3	117.5 (2)	C16—C17—Cl1	121.1 (18)
O2—C4—C5	121.6 (2)	C18—C17—Cl1	111.6 (18)
C3—C4—C5	120.9 (2)	C13—C18—C17	111.2 (12)
C6—C5—C4	116.9 (2)	C13—C18—H18	124.4
C6—C5—C7	123.5 (2)	C17—C18—H18	124.4
C4—C5—C7	119.5 (2)	C18'—C13'—C14'	120.0
C1—C6—C5	122.6 (2)	C18'—C13'—N1	121.4 (8)
C1—C6—H6	118.7	C14'—C13'—N1	118.4 (7)
C5—C6—H6	118.7	C13'—C14'—C15'	120.0
O3—C7—C5	121.9 (2)	C13'—C14'—H14'	120.0
O3—C7—C8	117.7 (2)	C15'—C14'—H14'	120.0
C5—C7—C8	120.4 (2)	C16'—C15'—C14'	120.0
C12—C8—C9	117.8 (2)	C16'—C15'—H15'	120.0
C12—C8—C7	122.5 (2)	C14'—C15'—H15'	120.0
C9—C8—C7	119.4 (3)	C17'—C16'—C15'	120.0
C10—C9—C8	120.9 (3)	C17'—C16'—H16'	120.0
C10—C9—H9	119.5	C15'—C16'—H16'	120.0
C8—C9—H9	119.5	C16'—C17'—C18'	120.0
C9—C10—C11	121.5 (3)	C16'—C17'—Cl1'	119.5 (8)
C9—C10—H10	119.3	C18'—C17'—Cl1'	120.5 (8)
C11—C10—H10	119.3	C13'—C18'—C17'	120.0
O4—C11—N1	119.4 (3)	C13'—C18'—H18'	120.0
O4—C11—C10	125.1 (3)	C17'—C18'—H18'	120.0
N1—C11—C10	115.5 (2)	C12—N1—C11	122.8 (2)
C8—C12—N1	121.5 (2)	C12—N1—C13'	118.3 (4)
C8—C12—H12	119.3	C11—N1—C13'	118.9 (4)
N1—C12—H12	119.3	C12—N1—C13	119.1 (9)
C18—C13—C14	125.9 (12)	C11—N1—C13	118.0 (9)
C18—C13—N1	118.1 (18)	C2—O1—H1	108 (3)
C14—C13—N1	114.7 (18)	C4—O2—H2	104 (2)
C13—C14—C15	116.8 (16)
C6—C1—C2—O1	178.2 (3)	C15—C16—C17—Cl1	175 (2)
C6—C1—C2—C3	−1.0 (4)	C14—C13—C18—C17	−5.7 (18)
O1—C2—C3—C4	−177.9 (2)	N1—C13—C18—C17	−172.1 (17)
C1—C2—C3—C4	1.2 (4)	C16—C17—C18—C13	4 (2)
C2—C3—C4—O2	179.3 (2)	Cl1—C17—C18—C13	−172.5 (17)
C2—C3—C4—C5	−1.9 (4)	C18'—C13'—C14'—C15'	0.0
O2—C4—C5—C6	−179.0 (2)	N1—C13'—C14'—C15'	−176.2 (8)
C3—C4—C5—C6	2.2 (4)	C13'—C14'—C15'—C16'	0.0
O2—C4—C5—C7	−2.9 (4)	C14'—C15'—C16'—C17'	0.0
C3—C4—C5—C7	178.4 (2)	C15'—C16'—C17'—C18'	0.0
C2—C1—C6—C5	1.4 (5)	C15'—C16'—C17'—Cl1'	−179.7 (7)
C4—C5—C6—C1	−2.0 (4)	C14'—C13'—C18'—C17'	0.0
C7—C5—C6—C1	−178.0 (3)	N1—C13'—C18'—C17'	176.0 (8)
C6—C5—C7—O3	162.1 (3)	C16'—C17'—C18'—C13'	0.0
C4—C5—C7—O3	−13.8 (4)	Cl1'—C17'—C18'—C13'	179.7 (7)
C6—C5—C7—C8	−19.3 (4)	C8—C12—N1—C11	−0.6 (4)
C4—C5—C7—C8	164.8 (2)	C8—C12—N1—C13'	176.6 (6)
O3—C7—C8—C12	136.6 (3)	C8—C12—N1—C13	175.5 (12)
C5—C7—C8—C12	−42.0 (4)	O4—C11—N1—C12	178.0 (2)
O3—C7—C8—C9	−36.4 (4)	C10—C11—N1—C12	−0.1 (4)
C5—C7—C8—C9	145.0 (3)	O4—C11—N1—C13'	0.7 (6)
C12—C8—C9—C10	2.1 (4)	C10—C11—N1—C13'	−177.3 (6)
C7—C8—C9—C10	175.4 (2)	O4—C11—N1—C13	1.8 (12)
C8—C9—C10—C11	−2.9 (4)	C10—C11—N1—C13	−176.2 (12)
C9—C10—C11—O4	−176.1 (3)	C18'—C13'—N1—C12	97.6 (6)
C9—C10—C11—N1	1.8 (4)	C14'—C13'—N1—C12	−86.3 (6)
C9—C8—C12—N1	−0.4 (4)	C18'—C13'—N1—C11	−85.0 (6)
C7—C8—C12—N1	−173.4 (2)	C14'—C13'—N1—C11	91.0 (6)
C18—C13—C14—C15	4.8 (13)	C18—C13—N1—C12	114.9 (13)
N1—C13—C14—C15	171.6 (15)	C14—C13—N1—C12	−53.0 (14)
C13—C14—C15—C16	−1.3 (16)	C18—C13—N1—C11	−68.8 (15)
C14—C15—C16—C17	0 (3)	C14—C13—N1—C11	123.3 (10)
C15—C16—C17—C18	−1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.91 (4)	1.75 (4)	2.587 (3)	152 (3)
O1—H1···O4i	0.87 (5)	1.79 (5)	2.655 (3)	175 (4)
C3—H3···O4i	0.93	2.50	3.165 (3)	129
C15—H15···O1ii	0.93	2.71	3.37 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.91 (4)	1.75 (4)	2.587 (3)	152 (3)
O1—H1⋯O4i	0.87 (5)	1.79 (5)	2.655 (3)	175 (4)
C3—H3⋯O4i	0.93	2.50	3.165 (3)	129
C15—H15⋯O1ii	0.93	2.71	3.37 (2)	129

Symmetry codes: (i) ; (ii) .