5-Chloro-8-hydr-oxy-6-methyl-1,4-naphthoquinone.

The mol-ecule of the title compound, C(11)H(7)ClO(3), is planar, with a maximum deviation of 0.0383 (10) Å from the naphthoquinone plane. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds. Short intra-molecular Cl⋯O [2.8234 (8) Å] and O⋯O [2.5530 (11) Å], and inter-molecular Cl⋯Cl [3.2777 (3) Å] contacts further stabilize the crystal structure.

Related literature

For the biological activity of the related compound 7-methyl­juglone, see: Mahapatra et al. (2007 ▶); Van der Kooy & Meyer (2006 ▶). For the synthesis of 7-methyl­juglone from the title compound, see: Musgrave & Skoyles (2001 ▶); Mahapatra et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H7ClO3

M = 222.62

Monoclinic,

a = 10.7546 (1) Å

b = 10.3104 (1) Å

c = 16.8370 (2) Å

β = 100.285 (1)°

V = 1836.96 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.40 mm−1

T = 100 K

0.30 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.891, T max = 0.945

17328 measured reflections

4015 independent reflections

3356 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.109

S = 1.07

4015 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010137/sj2597sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010137/sj2597Isup2.hkl

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

C11H7ClO3	F(000) = 912
Mr = 222.62	Dx = 1.610 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6307 reflections
a = 10.7546 (1) Å	θ = 2.8–30.1°
b = 10.3104 (1) Å	µ = 0.40 mm−1
c = 16.8370 (2) Å	T = 100 K
β = 100.285 (1)°	Block, red
V = 1836.96 (3) Å3	0.30 × 0.21 × 0.14 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	4015 independent reflections
Radiation source: fine-focus sealed tube	3356 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 35.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→17
Tmin = 0.891, Tmax = 0.945	k = −16→16
17328 measured reflections	l = −27→27

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.6106P] where P = (Fo2 + 2Fc2)/3
4015 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.60008 (2)	0.08776 (3)	0.687132 (14)	0.02314 (8)
O1	0.40351 (7)	0.18970 (8)	0.57005 (5)	0.02395 (16)
O2	0.64859 (7)	0.18264 (8)	0.31989 (4)	0.02085 (15)
O3	0.83772 (7)	0.06289 (8)	0.40048 (4)	0.02028 (14)
H1O3	0.7847	0.1042	0.3653	0.030*
C1	0.46492 (8)	0.18621 (9)	0.51561 (6)	0.01565 (16)
C2	0.40771 (9)	0.23850 (9)	0.43571 (6)	0.01789 (17)
H2A	0.3271	0.2743	0.4292	0.021*
C3	0.46720 (9)	0.23648 (9)	0.37229 (6)	0.01852 (17)
H3A	0.4275	0.2710	0.3232	0.022*
C4	0.59410 (9)	0.18056 (9)	0.37912 (5)	0.01556 (16)
C5	0.77541 (8)	0.06817 (8)	0.46273 (6)	0.01477 (15)
C6	0.83488 (8)	0.01527 (9)	0.53621 (6)	0.01568 (16)
H6A	0.9135	−0.0238	0.5394	0.019*
C7	0.77959 (8)	0.01969 (9)	0.60416 (5)	0.01563 (15)
C8	0.65972 (8)	0.07923 (9)	0.59849 (5)	0.01508 (15)
C9	0.59512 (8)	0.12905 (8)	0.52543 (5)	0.01356 (15)
C10	0.65466 (8)	0.12451 (8)	0.45647 (5)	0.01354 (15)
C11	0.84754 (10)	−0.03753 (11)	0.68182 (6)	0.02193 (19)
H11A	0.9265	−0.0738	0.6736	0.033*
H11B	0.7964	−0.1044	0.6993	0.033*
H11C	0.8632	0.0290	0.7222	0.033*

	U11	U22	U33	U12	U13	U23
Cl1	0.02101 (12)	0.03306 (14)	0.01720 (11)	0.00279 (9)	0.00841 (8)	0.00089 (8)
O1	0.0164 (3)	0.0311 (4)	0.0264 (4)	0.0055 (3)	0.0096 (3)	−0.0001 (3)
O2	0.0206 (3)	0.0258 (3)	0.0170 (3)	0.0004 (3)	0.0055 (3)	0.0009 (3)
O3	0.0172 (3)	0.0258 (3)	0.0200 (3)	0.0053 (3)	0.0093 (3)	0.0014 (3)
C1	0.0117 (3)	0.0146 (3)	0.0210 (4)	0.0004 (3)	0.0040 (3)	−0.0023 (3)
C2	0.0123 (4)	0.0162 (4)	0.0243 (4)	0.0018 (3)	0.0009 (3)	−0.0017 (3)
C3	0.0150 (4)	0.0188 (4)	0.0206 (4)	0.0015 (3)	0.0000 (3)	0.0006 (3)
C4	0.0146 (4)	0.0150 (3)	0.0170 (4)	−0.0012 (3)	0.0027 (3)	−0.0009 (3)
C5	0.0122 (3)	0.0152 (3)	0.0181 (4)	−0.0003 (3)	0.0058 (3)	−0.0017 (3)
C6	0.0115 (3)	0.0164 (4)	0.0193 (4)	0.0008 (3)	0.0034 (3)	−0.0012 (3)
C7	0.0126 (3)	0.0168 (4)	0.0171 (4)	−0.0006 (3)	0.0017 (3)	−0.0010 (3)
C8	0.0130 (3)	0.0174 (4)	0.0154 (4)	−0.0011 (3)	0.0043 (3)	−0.0013 (3)
C9	0.0103 (3)	0.0137 (3)	0.0172 (4)	−0.0002 (3)	0.0040 (3)	−0.0017 (3)
C10	0.0113 (3)	0.0141 (3)	0.0156 (3)	0.0001 (3)	0.0033 (3)	−0.0014 (3)
C11	0.0189 (4)	0.0279 (5)	0.0177 (4)	0.0024 (4)	−0.0001 (3)	0.0016 (3)

Cl1—C8	1.7287 (9)	C5—C6	1.3980 (13)
O1—C1	1.2222 (12)	C5—C10	1.4092 (12)
O2—C4	1.2438 (11)	C6—C7	1.3812 (13)
O3—C5	1.3423 (11)	C6—H6A	0.9300
O3—H1O3	0.8581	C7—C8	1.4156 (13)
C1—C2	1.4777 (14)	C7—C11	1.5002 (13)
C1—C9	1.5008 (12)	C8—C9	1.3980 (13)
C2—C3	1.3393 (14)	C9—C10	1.4234 (12)
C2—H2A	0.9300	C11—H11A	0.9600
C3—C4	1.4670 (13)	C11—H11B	0.9600
C3—H3A	0.9300	C11—H11C	0.9600
C4—C10	1.4667 (13)
C5—O3—H1O3	99.0	C6—C7—C8	118.69 (8)
O1—C1—C2	118.62 (8)	C6—C7—C11	119.62 (8)
O1—C1—C9	123.19 (9)	C8—C7—C11	121.69 (8)
C2—C1—C9	118.18 (8)	C9—C8—C7	121.48 (8)
C3—C2—C1	122.65 (8)	C9—C8—Cl1	122.56 (7)
C3—C2—H2A	118.7	C7—C8—Cl1	115.95 (7)
C1—C2—H2A	118.7	C8—C9—C10	118.71 (8)
C2—C3—C4	120.92 (9)	C8—C9—C1	123.27 (8)
C2—C3—H3A	119.5	C10—C9—C1	118.02 (8)
C4—C3—H3A	119.5	C5—C10—C9	119.69 (8)
O2—C4—C10	121.37 (8)	C5—C10—C4	119.08 (8)
O2—C4—C3	119.69 (8)	C9—C10—C4	121.21 (8)
C10—C4—C3	118.94 (8)	C7—C11—H11A	109.5
O3—C5—C6	117.51 (8)	C7—C11—H11B	109.5
O3—C5—C10	122.69 (8)	H11A—C11—H11B	109.5
C6—C5—C10	119.80 (8)	C7—C11—H11C	109.5
C7—C6—C5	121.57 (8)	H11A—C11—H11C	109.5
C7—C6—H6A	119.2	H11B—C11—H11C	109.5
C5—C6—H6A	119.2
O1—C1—C2—C3	−178.75 (9)	O1—C1—C9—C8	−2.55 (14)
C9—C1—C2—C3	0.15 (13)	C2—C1—C9—C8	178.61 (8)
C1—C2—C3—C4	0.34 (14)	O1—C1—C9—C10	176.82 (9)
C2—C3—C4—O2	−178.28 (9)	C2—C1—C9—C10	−2.03 (12)
C2—C3—C4—C10	1.01 (14)	O3—C5—C10—C9	−178.76 (8)
O3—C5—C6—C7	178.08 (8)	C6—C5—C10—C9	1.06 (13)
C10—C5—C6—C7	−1.75 (13)	O3—C5—C10—C4	−0.34 (13)
C5—C6—C7—C8	0.12 (13)	C6—C5—C10—C4	179.48 (8)
C5—C6—C7—C11	−179.54 (9)	C8—C9—C10—C5	1.20 (13)
C6—C7—C8—C9	2.23 (13)	C1—C9—C10—C5	−178.19 (8)
C11—C7—C8—C9	−178.11 (9)	C8—C9—C10—C4	−177.18 (8)
C6—C7—C8—Cl1	−177.07 (7)	C1—C9—C10—C4	3.43 (12)
C11—C7—C8—Cl1	2.59 (12)	O2—C4—C10—C5	−2.09 (13)
C7—C8—C9—C10	−2.87 (13)	C3—C4—C10—C5	178.63 (8)
Cl1—C8—C9—C10	176.38 (7)	O2—C4—C10—C9	176.30 (8)
C7—C8—C9—C1	176.48 (8)	C3—C4—C10—C9	−2.98 (13)
Cl1—C8—C9—C1	−4.26 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O2	0.86	1.73	2.5530 (11)	161
C2—H2A···O1i	0.93	2.51	3.4124 (12)	163
C3—H3A···O2ii	0.93	2.57	3.3000 (12)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O2	0.86	1.73	2.5530 (11)	161
C2—H2A⋯O1i	0.93	2.51	3.4124 (12)	163
C3—H3A⋯O2ii	0.93	2.57	3.3000 (12)	136

Symmetry codes: (i) ; (ii) .