2,3-Dichloro-5,8-dimeth-oxy-1,4-naphtho-quinone.

In the crystal structure of the title compound, C(12)H(8)Cl(2)O(4), mol-ecules crystallize in planes parallel to (-204) with an inter-planar distance of 3.288 (2) Å [centroid-centroid distance = 3.819 (2) and slippage = 1.932 (2) Å]. The structure features C-H⋯O inter-actions involving meth-oxy and aromatic H atoms and the carbonyl O atoms as well as a C-H⋯Cl inter-action involving an aromatic H atom. In addition there are short inter-halogen contacts between adjoining mol-ecules [Cl⋯Cl = 3.3709 (5) Å].

Related literature

For biological properties of the title compound, see: Huang et al. (1998 ▶); Copeland et al. (2007 ▶); Lien et al. (1997 ▶). For structures of related 2,3-dichloro-1,4-naphtho­quinone derivatives, see: Ikemoto et al. (1977 ▶); Rubio et al. (1985 ▶). For quinoid systems, see: Driebergen et al. (1986 ▶); Scheuermann et al. (2009 ▶).

Experimental

Crystal data

C12H8Cl2O4

M = 287.08

Monoclinic,

a = 9.9366 (2) Å

b = 15.6564 (3) Å

c = 14.8505 (3) Å

β = 103.782 (2)°

V = 2243.79 (8) Å3

Z = 8

Cu Kα radiation

μ = 5.27 mm−1

T = 123 K

0.81 × 0.30 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.154, T max = 0.418

8037 measured reflections

2199 independent reflections

2156 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.077

S = 1.09

2199 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812023926/bt5932sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023926/bt5932Isup2.hkl

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

C12H8Cl2O4	F(000) = 1168
Mr = 287.08	Dx = 1.700 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 6065 reflections
a = 9.9366 (2) Å	θ = 3.1–72.4°
b = 15.6564 (3) Å	µ = 5.27 mm−1
c = 14.8505 (3) Å	T = 123 K
β = 103.782 (2)°	Slab, pink
V = 2243.79 (8) Å3	0.81 × 0.30 × 0.23 mm
Z = 8

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2199 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2156 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 10.5081 pixels mm-1	θmax = 72.5°, θmin = 5.4°
ω scans	h = −12→12
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2007)	k = −19→18
Tmin = 0.154, Tmax = 0.418	l = −13→18
8037 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0452P)2 + 1.7012P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
2199 reflections	Δρmax = 0.31 e Å−3
166 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00077 (11)

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	0.22986 (3)	0.61933 (2)	0.50894 (2)	0.02353 (13)
Cl2	0.47240 (4)	0.73207 (2)	0.62182 (2)	0.02670 (14)
O1	0.29765 (11)	0.44185 (6)	0.51438 (7)	0.0247 (2)
O2	0.70729 (11)	0.63328 (7)	0.71429 (7)	0.0256 (2)
O3	0.83562 (11)	0.50132 (7)	0.79392 (7)	0.0266 (3)
O4	0.41728 (11)	0.30361 (6)	0.58176 (7)	0.0246 (2)
C1	0.39013 (13)	0.48023 (9)	0.56736 (9)	0.0163 (3)
C2	0.37962 (13)	0.57504 (9)	0.57239 (9)	0.0163 (3)
C3	0.48343 (14)	0.62303 (8)	0.62041 (9)	0.0169 (3)
C4	0.61546 (13)	0.58551 (9)	0.67577 (9)	0.0166 (3)
C5	0.62262 (13)	0.49062 (9)	0.68126 (9)	0.0160 (3)
C6	0.73632 (14)	0.45098 (9)	0.74118 (9)	0.0194 (3)
C7	0.74226 (15)	0.36157 (10)	0.74499 (10)	0.0233 (3)
H7A	0.8192	0.3346	0.7852	0.028*
C8	0.63901 (16)	0.31218 (9)	0.69163 (10)	0.0232 (3)
H8A	0.6467	0.2517	0.6946	0.028*
C9	0.52280 (15)	0.34971 (9)	0.63305 (10)	0.0193 (3)
C10	0.51411 (14)	0.43964 (9)	0.62756 (9)	0.0162 (3)
C11	0.94626 (15)	0.46147 (11)	0.86031 (11)	0.0291 (3)
H11A	1.0087	0.5054	0.8939	0.044*
H11B	0.9978	0.4235	0.8282	0.044*
H11C	0.9079	0.4282	0.9042	0.044*
C12	0.42089 (18)	0.21201 (9)	0.59175 (12)	0.0295 (3)
H12A	0.3370	0.1873	0.5518	0.044*
H12B	0.4255	0.1970	0.6565	0.044*
H12C	0.5027	0.1894	0.5737	0.044*

	U11	U22	U33	U12	U13	U23
Cl1	0.01650 (19)	0.0218 (2)	0.0275 (2)	0.00482 (11)	−0.00425 (14)	0.00124 (12)
Cl2	0.0297 (2)	0.01223 (19)	0.0314 (2)	0.00149 (12)	−0.00606 (15)	−0.00074 (12)
O1	0.0218 (5)	0.0195 (5)	0.0281 (5)	−0.0027 (4)	−0.0033 (4)	−0.0024 (4)
O2	0.0204 (5)	0.0211 (5)	0.0300 (6)	−0.0041 (4)	−0.0045 (4)	−0.0011 (4)
O3	0.0190 (5)	0.0279 (6)	0.0263 (5)	0.0043 (4)	−0.0075 (4)	0.0011 (4)
O4	0.0260 (5)	0.0131 (5)	0.0331 (6)	−0.0016 (4)	0.0036 (4)	−0.0014 (4)
C1	0.0152 (6)	0.0171 (7)	0.0167 (6)	−0.0015 (5)	0.0041 (5)	−0.0003 (5)
C2	0.0131 (6)	0.0182 (7)	0.0163 (6)	0.0032 (5)	0.0009 (5)	0.0019 (5)
C3	0.0194 (7)	0.0124 (7)	0.0182 (7)	0.0012 (5)	0.0030 (5)	0.0004 (5)
C4	0.0156 (6)	0.0192 (7)	0.0146 (6)	−0.0003 (5)	0.0024 (5)	0.0004 (5)
C5	0.0146 (6)	0.0173 (7)	0.0164 (6)	0.0024 (5)	0.0041 (5)	0.0015 (5)
C6	0.0165 (6)	0.0238 (7)	0.0181 (7)	0.0029 (5)	0.0042 (5)	0.0014 (5)
C7	0.0196 (7)	0.0248 (7)	0.0256 (7)	0.0093 (6)	0.0055 (6)	0.0090 (6)
C8	0.0244 (7)	0.0172 (7)	0.0298 (8)	0.0050 (5)	0.0104 (6)	0.0059 (6)
C9	0.0201 (7)	0.0177 (7)	0.0214 (7)	0.0006 (5)	0.0076 (5)	0.0009 (5)
C10	0.0168 (6)	0.0155 (7)	0.0172 (6)	0.0011 (5)	0.0057 (5)	0.0010 (5)
C11	0.0202 (7)	0.0375 (9)	0.0244 (7)	0.0104 (6)	−0.0050 (6)	0.0029 (6)
C12	0.0359 (9)	0.0140 (7)	0.0406 (9)	−0.0018 (6)	0.0129 (7)	−0.0020 (6)

Cl1—C2	1.7074 (13)	C5—C10	1.4233 (19)
Cl2—C3	1.7111 (13)	C6—C7	1.402 (2)
O1—C1	1.2166 (17)	C7—C8	1.375 (2)
O2—C4	1.2126 (17)	C7—H7A	0.9500
O3—C6	1.3564 (18)	C8—C9	1.399 (2)
O3—C11	1.4331 (17)	C8—H8A	0.9500
O4—C9	1.3492 (18)	C9—C10	1.4117 (18)
O4—C12	1.4413 (17)	C11—H11A	0.9800
C1—C10	1.4819 (19)	C11—H11B	0.9800
C1—C2	1.4911 (18)	C11—H11C	0.9800
C2—C3	1.3367 (19)	C12—H12A	0.9800
C3—C4	1.4927 (18)	C12—H12B	0.9800
C4—C5	1.4886 (18)	C12—H12C	0.9800
C5—C6	1.4052 (19)
C6—O3—C11	118.53 (12)	C6—C7—H7A	119.3
C9—O4—C12	118.51 (12)	C7—C8—C9	120.94 (13)
O1—C1—C10	124.72 (13)	C7—C8—H8A	119.5
O1—C1—C2	118.22 (12)	C9—C8—H8A	119.5
C10—C1—C2	117.05 (11)	O4—C9—C8	122.80 (13)
C3—C2—C1	122.14 (12)	O4—C9—C10	118.19 (12)
C3—C2—Cl1	121.77 (11)	C8—C9—C10	119.00 (13)
C1—C2—Cl1	116.03 (10)	C9—C10—C5	119.95 (12)
C2—C3—C4	122.54 (12)	C9—C10—C1	119.55 (12)
C2—C3—Cl2	121.59 (11)	C5—C10—C1	120.49 (12)
C4—C3—Cl2	115.87 (10)	O3—C11—H11A	109.5
O2—C4—C5	124.68 (12)	O3—C11—H11B	109.5
O2—C4—C3	118.74 (12)	H11A—C11—H11B	109.5
C5—C4—C3	116.56 (11)	O3—C11—H11C	109.5
C6—C5—C10	119.64 (13)	H11A—C11—H11C	109.5
C6—C5—C4	119.75 (12)	H11B—C11—H11C	109.5
C10—C5—C4	120.60 (12)	O4—C12—H12A	109.5
O3—C6—C7	122.63 (13)	O4—C12—H12B	109.5
O3—C6—C5	118.27 (13)	H12A—C12—H12B	109.5
C7—C6—C5	119.10 (13)	O4—C12—H12C	109.5
C8—C7—C6	121.33 (13)	H12A—C12—H12C	109.5
C8—C7—H7A	119.3	H12B—C12—H12C	109.5
O1—C1—C2—C3	−172.16 (13)	C4—C5—C6—C7	−179.42 (12)
C10—C1—C2—C3	7.53 (19)	O3—C6—C7—C8	179.06 (13)
O1—C1—C2—Cl1	5.05 (16)	C5—C6—C7—C8	−0.2 (2)
C10—C1—C2—Cl1	−175.27 (9)	C6—C7—C8—C9	−1.4 (2)
C1—C2—C3—C4	−2.5 (2)	C12—O4—C9—C8	3.6 (2)
Cl1—C2—C3—C4	−179.59 (10)	C12—O4—C9—C10	−175.82 (12)
C1—C2—C3—Cl2	177.39 (10)	C7—C8—C9—O4	−177.91 (13)
Cl1—C2—C3—Cl2	0.34 (17)	C7—C8—C9—C10	1.5 (2)
C2—C3—C4—O2	176.86 (13)	O4—C9—C10—C5	179.39 (12)
Cl2—C3—C4—O2	−3.09 (17)	C8—C9—C10—C5	−0.06 (19)
C2—C3—C4—C5	−4.63 (19)	O4—C9—C10—C1	0.79 (18)
Cl2—C3—C4—C5	175.42 (9)	C8—C9—C10—C1	−178.66 (12)
O2—C4—C5—C6	6.3 (2)	C6—C5—C10—C9	−1.52 (19)
C3—C4—C5—C6	−172.15 (12)	C4—C5—C10—C9	179.58 (11)
O2—C4—C5—C10	−174.84 (13)	C6—C5—C10—C1	177.06 (11)
C3—C4—C5—C10	6.75 (18)	C4—C5—C10—C1	−1.83 (18)
C11—O3—C6—C7	−4.1 (2)	O1—C1—C10—C9	−6.9 (2)
C11—O3—C6—C5	175.23 (12)	C2—C1—C10—C9	173.40 (11)
C10—C5—C6—O3	−177.66 (12)	O1—C1—C10—C5	174.48 (12)
C4—C5—C6—O3	1.24 (18)	C2—C1—C10—C5	−5.19 (18)
C10—C5—C6—C7	1.67 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cl2i	0.95	2.72	3.6593 (14)	169
C8—H8A···O2i	0.95	2.54	3.3337 (18)	142
C11—H11C···O1ii	0.98	2.62	3.4030 (19)	137
C12—H12A···O1iii	0.98	2.49	3.3723 (19)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Cl2i	0.95	2.72	3.6593 (14)	169
C8—H8A⋯O2i	0.95	2.54	3.3337 (18)	142
C11—H11C⋯O1ii	0.98	2.62	3.4030 (19)	137
C12—H12A⋯O1iii	0.98	2.49	3.3723 (19)	149

Symmetry codes: (i) ; (ii) ; (iii) .