1-(5-Chloro-2,4-dihydroxy-phen-yl)-2-(4-ethoxy-phen-yl)ethanone.

The structure of the title compound, C(16)H(15)ClO(4), contains aryl rings which are inclined by 75.6 (1)° to each other. It displays intra-molecular O-H⋯O hydrogen bonding between the 2-hydr-oxy and carbonyl groups, forming a six-membered ring. Furthermore, the 4-hydr-oxy group, acting as a hydrogen-bond donor, is bound to the O atom of the 2-hydr-oxy group of another mol-ecule.

Related literature

For related literature, see: Anderson & Garner (1997 ▶); Fokialakis et al. (2004 ▶); Papoutsi et al. (2007 ▶); Anthony (2002 ▶); Barnes (1998 ▶); Barnes & Peterson (1995 ▶); Dixon & Ferreira (2002 ▶); Greenwood et al. (2000 ▶); Setchell (1998 ▶); Whalley et al. (2000 ▶). For a related structure, see: Arumugan et al. (2007 ▶).

Experimental

Crystal data

C16H15ClO4

M = 306.73

Monoclinic,

a = 19.255 (6) Å

b = 4.6454 (15) Å

c = 31.109 (11) Å

β = 90.519 (7)°

V = 2782.5 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 125 (2) K

0.11 × 0.03 × 0.03 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.983, T max = 0.997

8448 measured reflections

2515 independent reflections

1401 reflections with I > 2σ(I)

R int = 0.091

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.101

S = 0.89

2515 reflections

199 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2001 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030699/wn2279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030699/wn2279Isup2.hkl

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

C16H15ClO4	F(000) = 1280
Mr = 306.73	Dx = 1.464 Mg m−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 19.255 (6) Å	Cell parameters from 306 reflections
b = 4.6454 (15) Å	θ = 12–28°
c = 31.109 (11) Å	µ = 0.29 mm−1
β = 90.519 (7)°	T = 125 K
V = 2782.5 (16) Å3	Prism, colourless
Z = 8	0.11 × 0.03 × 0.03 mm

Bruker SMART diffractometer	2515 independent reflections
Radiation source: fine-focus sealed tube	1401 reflections with I > 2σ(I)
graphite	Rint = 0.091
Detector resolution: 0.83 pixels mm-1	θmax = 25.4°, θmin = 2.1°
φ and ω scans	h = −22→23
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −5→5
Tmin = 0.983, Tmax = 0.997	l = −37→31
8448 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ2(Fo2) + (0.0438P)2] where P = (Fo2 + 2Fc2)/3
2515 reflections	(Δ/σ)max = 0.033
199 parameters	Δρmax = 0.28 e Å−3
2 restraints	Δρmin = −0.27 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	0.33978 (15)	0.7593 (6)	0.18759 (10)	0.0179 (7)
C2	0.39148 (16)	0.8676 (6)	0.21571 (10)	0.0178 (8)
O2	0.37615 (11)	1.0672 (4)	0.24646 (7)	0.0217 (5)
H2O	0.3277 (6)	1.130 (8)	0.2439 (13)	0.076 (14)*
C3	0.45909 (15)	0.7723 (6)	0.21336 (10)	0.0189 (7)
H3A	0.4931	0.8474	0.2326	0.023*
C4	0.47810 (16)	0.5683 (6)	0.18323 (10)	0.0193 (8)
O4	0.54308 (11)	0.4628 (5)	0.18053 (7)	0.0258 (6)
H4O	0.5655 (16)	0.516 (8)	0.2078 (6)	0.064 (13)*
C5	0.42808 (16)	0.4638 (6)	0.15414 (10)	0.0195 (8)
Cl5	0.45154 (4)	0.21806 (16)	0.11487 (3)	0.0265 (3)
C6	0.36084 (16)	0.5567 (6)	0.15684 (10)	0.0192 (8)
H6A	0.3273	0.4817	0.1373	0.023*
C7	0.26827 (16)	0.8586 (6)	0.19047 (10)	0.0193 (8)
O7	0.25248 (11)	1.0457 (5)	0.21737 (7)	0.0295 (6)
C8	0.21213 (15)	0.7476 (6)	0.16079 (10)	0.0234 (8)
H8A	0.2267	0.5604	0.1486	0.028*
H8B	0.1692	0.7156	0.1774	0.028*
C9	0.19729 (16)	0.9550 (6)	0.12476 (10)	0.0187 (8)
C10	0.24738 (17)	1.0299 (7)	0.09503 (11)	0.0258 (8)
H10A	0.2925	0.9486	0.0974	0.031*
C11	0.23309 (16)	1.2204 (7)	0.06193 (10)	0.0270 (8)
H11A	0.2681	1.2687	0.0419	0.032*
C12	0.16775 (17)	1.3401 (7)	0.05814 (11)	0.0239 (8)
C13	0.11677 (16)	1.2740 (6)	0.08744 (10)	0.0234 (8)
H13A	0.0719	1.3582	0.0851	0.028*
C14	0.13229 (16)	1.0809 (6)	0.12065 (10)	0.0222 (8)
H14A	0.0974	1.0349	0.1409	0.027*
O12	0.15829 (10)	1.5204 (5)	0.02307 (7)	0.0293 (6)
C15	0.09030 (16)	1.6385 (7)	0.01654 (11)	0.0271 (9)
H15A	0.0773	1.7614	0.0412	0.033*
H15B	0.0556	1.4824	0.0136	0.033*
C16	0.09290 (17)	1.8138 (7)	−0.02397 (11)	0.0336 (9)
H16A	0.0472	1.8999	−0.0296	0.050*
H16B	0.1055	1.6894	−0.0481	0.050*
H16C	0.1276	1.9667	−0.0207	0.050*

	U11	U22	U33	U12	U13	U23
C1	0.0173 (17)	0.0189 (17)	0.0175 (18)	−0.0018 (14)	−0.0035 (14)	0.0016 (14)
C2	0.0209 (19)	0.0137 (16)	0.019 (2)	−0.0004 (14)	−0.0014 (15)	0.0023 (13)
O2	0.0231 (13)	0.0224 (12)	0.0195 (13)	0.0028 (10)	−0.0057 (11)	−0.0029 (10)
C3	0.0188 (17)	0.0197 (17)	0.0181 (18)	−0.0015 (15)	−0.0058 (14)	0.0000 (15)
C4	0.0155 (17)	0.0210 (18)	0.021 (2)	0.0020 (15)	−0.0025 (15)	0.0071 (15)
O4	0.0217 (13)	0.0300 (14)	0.0257 (15)	0.0023 (11)	−0.0048 (11)	−0.0025 (11)
C5	0.0269 (19)	0.0146 (17)	0.0170 (19)	−0.0009 (15)	−0.0009 (16)	0.0008 (14)
Cl5	0.0277 (5)	0.0265 (5)	0.0250 (5)	0.0027 (4)	−0.0029 (4)	−0.0061 (4)
C6	0.0208 (18)	0.0156 (17)	0.021 (2)	0.0002 (14)	−0.0031 (15)	−0.0006 (14)
C7	0.0247 (19)	0.0157 (17)	0.017 (2)	−0.0003 (14)	−0.0004 (16)	0.0028 (14)
O7	0.0270 (13)	0.0342 (14)	0.0273 (15)	0.0057 (11)	−0.0066 (11)	−0.0070 (11)
C8	0.0191 (17)	0.0207 (18)	0.030 (2)	−0.0013 (15)	−0.0065 (15)	0.0011 (16)
C9	0.0183 (18)	0.0181 (18)	0.020 (2)	−0.0014 (15)	−0.0037 (16)	−0.0024 (14)
C10	0.0191 (18)	0.031 (2)	0.028 (2)	0.0033 (16)	−0.0058 (17)	−0.0016 (17)
C11	0.0193 (18)	0.038 (2)	0.024 (2)	−0.0013 (17)	0.0011 (15)	−0.0004 (17)
C12	0.029 (2)	0.0213 (18)	0.021 (2)	−0.0015 (15)	−0.0079 (17)	−0.0006 (15)
C13	0.0203 (17)	0.0201 (18)	0.030 (2)	0.0024 (15)	−0.0057 (16)	−0.0024 (16)
C14	0.0222 (19)	0.0230 (18)	0.021 (2)	−0.0043 (15)	0.0019 (16)	−0.0006 (15)
O12	0.0236 (13)	0.0358 (14)	0.0285 (15)	0.0003 (11)	−0.0052 (11)	0.0087 (11)
C15	0.0272 (19)	0.0232 (18)	0.031 (2)	0.0013 (15)	−0.0077 (17)	0.0063 (15)
C16	0.035 (2)	0.035 (2)	0.031 (2)	0.0023 (18)	−0.0047 (18)	0.0049 (17)

C1—C6	1.404 (4)	C9—C14	1.386 (4)
C1—C2	1.412 (4)	C9—C10	1.387 (4)
C1—C7	1.456 (4)	C10—C11	1.384 (4)
C2—O2	1.366 (4)	C10—H10A	0.9500
C2—C3	1.378 (4)	C11—C12	1.380 (4)
O2—H2O	0.9799 (11)	C11—H11A	0.9500
C3—C4	1.385 (4)	C12—C13	1.380 (5)
C3—H3A	0.9500	C12—O12	1.386 (4)
C4—O4	1.347 (3)	C13—C14	1.398 (4)
C4—C5	1.402 (4)	C13—H13A	0.9500
O4—H4O	0.9800 (11)	C14—H14A	0.9500
C5—C6	1.368 (4)	O12—C15	1.432 (4)
C5—Cl5	1.735 (3)	C15—C16	1.502 (4)
C6—H6A	0.9500	C15—H15A	0.9900
C7—O7	1.246 (4)	C15—H15B	0.9900
C7—C8	1.506 (4)	C16—H16A	0.9800
C8—C9	1.504 (4)	C16—H16B	0.9800
C8—H8A	0.9900	C16—H16C	0.9800
C8—H8B	0.9900
C6—C1—C2	117.0 (3)	C14—C9—C8	120.3 (3)
C6—C1—C7	122.2 (3)	C10—C9—C8	122.0 (3)
C2—C1—C7	120.7 (3)	C11—C10—C9	121.5 (3)
O2—C2—C3	117.7 (3)	C11—C10—H10A	119.3
O2—C2—C1	121.3 (3)	C9—C10—H10A	119.3
C3—C2—C1	120.9 (3)	C12—C11—C10	119.8 (3)
C2—O2—H2O	111 (2)	C12—C11—H11A	120.1
C2—C3—C4	120.8 (3)	C10—C11—H11A	120.1
C2—C3—H3A	119.6	C11—C12—C13	120.5 (3)
C4—C3—H3A	119.6	C11—C12—O12	115.1 (3)
O4—C4—C3	122.8 (3)	C13—C12—O12	124.4 (3)
O4—C4—C5	117.8 (3)	C12—C13—C14	118.8 (3)
C3—C4—C5	119.3 (3)	C12—C13—H13A	120.6
C4—O4—H4O	105 (2)	C14—C13—H13A	120.6
C6—C5—C4	119.7 (3)	C9—C14—C13	121.7 (3)
C6—C5—Cl5	120.2 (2)	C9—C14—H14A	119.1
C4—C5—Cl5	120.0 (2)	C13—C14—H14A	119.1
C5—C6—C1	122.2 (3)	C12—O12—C15	117.2 (3)
C5—C6—H6A	118.9	O12—C15—C16	106.8 (3)
C1—C6—H6A	118.9	O12—C15—H15A	110.4
O7—C7—C1	119.9 (3)	C16—C15—H15A	110.4
O7—C7—C8	118.2 (3)	O12—C15—H15B	110.4
C1—C7—C8	121.9 (3)	C16—C15—H15B	110.4
C9—C8—C7	111.6 (2)	H15A—C15—H15B	108.6
C9—C8—H8A	109.3	C15—C16—H16A	109.5
C7—C8—H8A	109.3	C15—C16—H16B	109.5
C9—C8—H8B	109.3	H16A—C16—H16B	109.5
C7—C8—H8B	109.3	C15—C16—H16C	109.5
H8A—C8—H8B	108.0	H16A—C16—H16C	109.5
C14—C9—C10	117.7 (3)	H16B—C16—H16C	109.5
C6—C1—C2—O2	179.5 (3)	C2—C1—C7—C8	179.8 (3)
C7—C1—C2—O2	0.3 (4)	O7—C7—C8—C9	78.3 (4)
C6—C1—C2—C3	−1.4 (4)	C1—C7—C8—C9	−100.0 (3)
C7—C1—C2—C3	179.4 (3)	C7—C8—C9—C14	−117.3 (3)
O2—C2—C3—C4	179.4 (3)	C7—C8—C9—C10	61.9 (4)
C1—C2—C3—C4	0.2 (5)	C14—C9—C10—C11	−0.9 (5)
C2—C3—C4—O4	−178.1 (3)	C8—C9—C10—C11	179.8 (3)
C2—C3—C4—C5	1.6 (5)	C9—C10—C11—C12	0.1 (5)
O4—C4—C5—C6	177.4 (3)	C10—C11—C12—C13	0.8 (5)
C3—C4—C5—C6	−2.3 (5)	C10—C11—C12—O12	−177.9 (3)
O4—C4—C5—Cl5	−2.6 (4)	C11—C12—C13—C14	−0.8 (5)
C3—C4—C5—Cl5	177.6 (2)	O12—C12—C13—C14	177.8 (3)
C4—C5—C6—C1	1.1 (5)	C10—C9—C14—C13	0.9 (5)
Cl5—C5—C6—C1	−178.8 (2)	C8—C9—C14—C13	−179.8 (3)
C2—C1—C6—C5	0.7 (5)	C12—C13—C14—C9	−0.1 (5)
C7—C1—C6—C5	179.9 (3)	C11—C12—O12—C15	176.9 (3)
C6—C1—C7—O7	−177.6 (3)	C13—C12—O12—C15	−1.7 (4)
C2—C1—C7—O7	1.5 (4)	C12—O12—C15—C16	−177.7 (3)
C6—C1—C7—C8	0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O7	0.98 (1)	1.71 (3)	2.542 (3)	141 (3)
O4—H4O···O2i	0.98 (1)	1.82 (1)	2.784 (3)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O7	0.98 (1)	1.71 (3)	2.542 (3)	141 (3)
O4—H4O⋯O2i	0.98 (1)	1.821 (9)	2.784 (3)	167 (3)

Symmetry code: (i) .