6,8-Di-chloro-4-oxochromene-3-carbalde-hyde.

The asymmetric unit of the title compound, C10H4Cl2O3, contain two essentially planar independent mol-ecules (mean atomic deviations from the corresponding least-square planes are 0.041 and 0.045 Å for mol-ecules 1 and 2, respectively). In the crystal, mol-ecules are linked through a pair of halogen bonds [Cl⋯O separations are 3.044 (5) and 3.033 (6) Å, C-Cl⋯O angles are 160.4 (3) and 162.8 (3)°, and C=O⋯Cl angles are 138.7 (4) and 139.6 (4)°, respectively, in mol-ecules 1 and 2] and C-H⋯O hydrogen bonds into slightly folded bands [the dihedral angle between the planes of neighboring mol-ecules is 8.6 (2)°] along the c-axis direction.

Related literature

For the biological activity of the title and related compounds, see: Shim et al. (2003 ▶); Kawase et al. (2007 ▶); Dückert et al. (2012 ▶). For related structures, see: Ishikawa et al. (2013a ▶,b ▶). For halogen bonding, see: Auffinger et al. (2004 ▶); Metrangolo et al. (2005 ▶); Wilcken et al. (2013 ▶).

Experimental

Crystal data

C10H4Cl2O3

M = 243.05

Triclinic,

a = 8.288 (8) Å

b = 8.325 (7) Å

c = 13.706 (7) Å

α = 96.55 (6)°

β = 92.23 (7)°

γ = 101.98 (7)°

V = 917.2 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.68 mm−1

T = 100 K

0.42 × 0.22 × 0.08 mm

Data collection

Rigaku AFC-7R diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.841, T max = 0.947

5130 measured reflections

4203 independent reflections

2596 reflections with F 2 > 2σ(F 2)

R int = 0.057

3 standard reflections every 150 reflections intensity decay: 4.9%

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.212

S = 1.10

4203 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.79 e Å−3

Data collection: WinAFC (Rigaku, 1999 ▶); cell refinement: WinAFC; data reduction: WinAFC; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536813022228/ld2111sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022228/ld2111Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022228/ld2111Isup3.cml

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

C10H4Cl2O3	Z = 4
Mr = 243.05	F(000) = 488.00
Triclinic, P1	Dx = 1.760 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.288 (8) Å	Cell parameters from 23 reflections
b = 8.325 (7) Å	θ = 15.2–17.4°
c = 13.706 (7) Å	µ = 0.68 mm−1
α = 96.55 (6)°	T = 100 K
β = 92.23 (7)°	Prismatic, colourless
γ = 101.98 (7)°	0.42 × 0.22 × 0.08 mm
V = 917.2 (13) Å3

Rigaku AFC-7R diffractometer	Rint = 0.057
ω–2θ scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −10→6
Tmin = 0.841, Tmax = 0.947	k = −10→10
5130 measured reflections	l = −17→17
4203 independent reflections	3 standard reflections every 150 reflections
2596 reflections with F2 > 2σ(F2)	intensity decay: 4.9%

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.212	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0531P)2 + 6.620P] where P = (Fo2 + 2Fc2)/3
4203 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.79 e Å−3
Primary atom site location: structure-invariant direct methods

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
Cl1a	0.9284 (2)	0.7180 (2)	−0.05206 (12)	0.0275 (4)
Cl2a	0.8997 (2)	0.60177 (19)	0.32529 (11)	0.0243 (4)
Cl1b	0.8654 (3)	1.0637 (2)	0.20783 (12)	0.0293 (4)
Cl2b	0.7665 (2)	1.01839 (19)	0.59010 (11)	0.0246 (4)
O1a	0.6255 (6)	0.3339 (5)	0.2521 (3)	0.0218 (10)
O2a	0.4506 (6)	0.1743 (6)	−0.0336 (4)	0.0277 (11)
O3a	0.2398 (7)	−0.0767 (6)	0.1869 (4)	0.0319 (12)
O1b	0.4940 (6)	0.7493 (6)	0.5162 (3)	0.0219 (10)
O2b	0.3559 (6)	0.5491 (6)	0.2305 (3)	0.0291 (11)
O3b	0.1021 (7)	0.3424 (6)	0.4522 (4)	0.0326 (12)
C1a	0.4980 (8)	0.2042 (8)	0.2288 (5)	0.0221 (13)
C2a	0.4342 (8)	0.1454 (8)	0.1358 (5)	0.0197 (13)
C3a	0.5023 (8)	0.2255 (8)	0.0520 (5)	0.0217 (13)
C4a	0.7126 (9)	0.4638 (8)	0.0063 (5)	0.0242 (14)
C5a	0.8382 (8)	0.5956 (8)	0.0344 (5)	0.0201 (13)
C6a	0.9020 (8)	0.6399 (8)	0.1321 (5)	0.0202 (13)
C7a	0.8290 (8)	0.5497 (8)	0.2026 (5)	0.0197 (13)
C8a	0.6945 (8)	0.4171 (8)	0.1770 (5)	0.0202 (13)
C9a	0.6370 (9)	0.3695 (8)	0.0784 (5)	0.0207 (13)
C10a	0.2954 (9)	−0.0026 (8)	0.1204 (5)	0.0250 (14)
C1b	0.3630 (8)	0.6197 (8)	0.4918 (5)	0.0220 (13)
C2b	0.3130 (8)	0.5479 (8)	0.4003 (5)	0.0217 (13)
C3b	0.3958 (8)	0.6127 (8)	0.3161 (5)	0.0214 (13)
C4b	0.6216 (8)	0.8361 (8)	0.2689 (5)	0.0220 (13)
C5b	0.7526 (8)	0.9654 (8)	0.2961 (5)	0.0227 (14)
C6b	0.8016 (9)	1.0234 (8)	0.3958 (5)	0.0234 (14)
C7b	0.7127 (8)	0.9495 (8)	0.4674 (5)	0.0217 (13)
C8b	0.5792 (8)	0.8170 (8)	0.4411 (5)	0.0188 (13)
C9b	0.5333 (8)	0.7557 (8)	0.3414 (5)	0.0190 (13)
C10b	0.1768 (9)	0.4034 (8)	0.3852 (5)	0.0238 (14)
H1a	0.4491	0.1499	0.2811	0.0265*
H2a	0.6755	0.4349	−0.0611	0.0290*
H3a	0.9933	0.7302	0.1493	0.0243*
H4a	0.2484	−0.0406	0.0555	0.0300*
H1b	0.3024	0.5769	0.5440	0.0264*
H2b	0.5904	0.8006	0.2012	0.0264*
H3b	0.8945	1.1120	0.4131	0.0281*
H4b	0.1440	0.3536	0.3196	0.0286*

	U11	U22	U33	U12	U13	U23
Cl1a	0.0338 (9)	0.0277 (9)	0.0216 (8)	0.0044 (7)	0.0053 (7)	0.0088 (6)
Cl2a	0.0312 (9)	0.0231 (8)	0.0166 (7)	0.0037 (7)	−0.0028 (6)	−0.0007 (6)
Cl1b	0.0345 (10)	0.0287 (9)	0.0246 (8)	0.0034 (8)	0.0082 (7)	0.0071 (7)
Cl2b	0.0311 (9)	0.0232 (8)	0.0171 (7)	0.0031 (7)	−0.0008 (6)	−0.0016 (6)
O1a	0.034 (3)	0.019 (3)	0.012 (2)	0.0034 (19)	0.0043 (18)	0.0014 (16)
O2a	0.035 (3)	0.032 (3)	0.014 (3)	0.005 (3)	−0.0023 (19)	−0.0005 (18)
O3a	0.037 (3)	0.030 (3)	0.023 (3)	−0.005 (3)	0.006 (2)	0.002 (2)
O1b	0.029 (3)	0.021 (3)	0.014 (2)	0.0013 (19)	0.0014 (18)	0.0028 (17)
O2b	0.035 (3)	0.035 (3)	0.014 (3)	0.003 (3)	−0.0017 (19)	−0.0023 (19)
O3b	0.036 (3)	0.032 (3)	0.025 (3)	−0.007 (3)	−0.002 (3)	0.005 (2)
C1a	0.025 (4)	0.022 (4)	0.020 (3)	0.006 (3)	0.001 (3)	0.004 (3)
C2a	0.020 (4)	0.021 (3)	0.018 (3)	0.005 (3)	0.003 (3)	0.001 (3)
C3a	0.026 (4)	0.020 (3)	0.019 (3)	0.007 (3)	−0.001 (3)	−0.001 (3)
C4a	0.033 (4)	0.025 (4)	0.013 (3)	0.003 (3)	0.003 (3)	0.004 (3)
C5a	0.028 (4)	0.019 (3)	0.017 (3)	0.010 (3)	0.007 (3)	0.006 (3)
C6a	0.025 (4)	0.017 (3)	0.019 (3)	0.004 (3)	0.003 (3)	0.002 (3)
C7a	0.025 (4)	0.020 (3)	0.014 (3)	0.006 (3)	−0.001 (3)	−0.001 (3)
C8a	0.024 (4)	0.019 (3)	0.017 (3)	0.004 (3)	0.002 (3)	0.004 (3)
C9a	0.030 (4)	0.018 (3)	0.015 (3)	0.009 (3)	0.002 (3)	0.001 (3)
C10a	0.030 (4)	0.019 (3)	0.024 (4)	0.004 (3)	−0.002 (3)	−0.001 (3)
C1b	0.027 (4)	0.019 (3)	0.021 (3)	0.006 (3)	0.004 (3)	0.002 (3)
C2b	0.023 (4)	0.025 (4)	0.018 (3)	0.007 (3)	−0.001 (3)	0.002 (3)
C3b	0.028 (4)	0.022 (4)	0.017 (3)	0.011 (3)	−0.000 (3)	0.002 (3)
C4b	0.027 (4)	0.021 (3)	0.018 (3)	0.004 (3)	0.004 (3)	0.002 (3)
C5b	0.028 (4)	0.023 (4)	0.022 (4)	0.012 (3)	0.006 (3)	0.008 (3)
C6b	0.027 (4)	0.020 (4)	0.022 (4)	0.004 (3)	−0.003 (3)	0.001 (3)
C7b	0.026 (4)	0.024 (4)	0.016 (3)	0.010 (3)	−0.000 (3)	0.001 (3)
C8b	0.023 (4)	0.024 (4)	0.014 (3)	0.013 (3)	0.005 (3)	0.006 (3)
C9b	0.020 (3)	0.023 (3)	0.017 (3)	0.013 (3)	0.000 (3)	0.003 (3)
C10b	0.031 (4)	0.019 (3)	0.020 (3)	0.004 (3)	0.004 (3)	0.000 (3)

Cl1a—C5a	1.740 (7)	C7a—C8a	1.398 (8)
Cl2a—C7a	1.735 (6)	C8a—C9a	1.401 (9)
Cl1b—C5b	1.733 (7)	C1b—C2b	1.338 (9)
Cl2b—C7b	1.723 (6)	C2b—C3b	1.464 (9)
O1a—C1a	1.344 (7)	C2b—C10b	1.458 (9)
O1a—C8a	1.381 (8)	C3b—C9b	1.465 (8)
O2a—C3a	1.229 (8)	C4b—C5b	1.367 (9)
O3a—C10a	1.210 (9)	C4b—C9b	1.405 (9)
O1b—C1b	1.363 (7)	C5b—C6b	1.411 (9)
O1b—C8b	1.379 (8)	C6b—C7b	1.376 (10)
O2b—C3b	1.233 (7)	C7b—C8b	1.393 (8)
O3b—C10b	1.227 (9)	C8b—C9b	1.412 (8)
C1a—C2a	1.356 (9)	C1a—H1a	0.950
C2a—C3a	1.467 (9)	C4a—H2a	0.950
C2a—C10a	1.490 (9)	C6a—H3a	0.950
C3a—C9a	1.459 (9)	C10a—H4a	0.950
C4a—C5a	1.355 (9)	C1b—H1b	0.950
C4a—C9a	1.416 (9)	C4b—H2b	0.950
C5a—C6a	1.401 (9)	C6b—H3b	0.950
C6a—C7a	1.373 (9)	C10b—H4b	0.950
C1a—O1a—C8a	118.3 (5)	C5b—C4b—C9b	119.9 (6)
C1b—O1b—C8b	118.1 (5)	Cl1b—C5b—C4b	120.6 (5)
O1a—C1a—C2a	124.6 (6)	Cl1b—C5b—C6b	117.6 (5)
C1a—C2a—C3a	120.4 (6)	C4b—C5b—C6b	121.9 (6)
C1a—C2a—C10a	118.9 (6)	C5b—C6b—C7b	118.9 (6)
C3a—C2a—C10a	120.7 (6)	Cl2b—C7b—C6b	120.4 (5)
O2a—C3a—C2a	122.6 (6)	Cl2b—C7b—C8b	119.6 (5)
O2a—C3a—C9a	122.9 (6)	C6b—C7b—C8b	120.0 (6)
C2a—C3a—C9a	114.5 (5)	O1b—C8b—C7b	117.3 (5)
C5a—C4a—C9a	119.4 (6)	O1b—C8b—C9b	121.6 (5)
Cl1a—C5a—C4a	120.3 (5)	C7b—C8b—C9b	121.1 (6)
Cl1a—C5a—C6a	117.0 (5)	C3b—C9b—C4b	121.9 (6)
C4a—C5a—C6a	122.7 (6)	C3b—C9b—C8b	119.8 (6)
C5a—C6a—C7a	118.3 (6)	C4b—C9b—C8b	118.2 (5)
Cl2a—C7a—C6a	120.3 (5)	O3b—C10b—C2b	123.8 (6)
Cl2a—C7a—C8a	119.0 (5)	O1a—C1a—H1a	117.700
C6a—C7a—C8a	120.6 (6)	C2a—C1a—H1a	117.702
O1a—C8a—C7a	117.4 (5)	C5a—C4a—H2a	120.314
O1a—C8a—C9a	122.2 (5)	C9a—C4a—H2a	120.307
C7a—C8a—C9a	120.4 (6)	C5a—C6a—H3a	120.850
C3a—C9a—C4a	121.6 (6)	C7a—C6a—H3a	120.844
C3a—C9a—C8a	119.9 (6)	O3a—C10a—H4a	118.481
C4a—C9a—C8a	118.5 (6)	C2a—C10a—H4a	118.489
O3a—C10a—C2a	123.0 (6)	O1b—C1b—H1b	117.382
O1b—C1b—C2b	125.2 (6)	C2b—C1b—H1b	117.374
C1b—C2b—C3b	120.2 (6)	C5b—C4b—H2b	120.070
C1b—C2b—C10b	119.4 (6)	C9b—C4b—H2b	120.068
C3b—C2b—C10b	120.3 (6)	C5b—C6b—H3b	120.568
O2b—C3b—C2b	122.6 (6)	C7b—C6b—H3b	120.567
O2b—C3b—C9b	122.5 (6)	O3b—C10b—H4b	118.104
C2b—C3b—C9b	114.9 (5)	C2b—C10b—H4b	118.102
C1a—O1a—C8a—C7a	−178.8 (6)	O1a—C8a—C9a—C3a	−1.4 (10)
C1a—O1a—C8a—C9a	−0.7 (9)	O1a—C8a—C9a—C4a	178.7 (6)
C8a—O1a—C1a—C2a	1.9 (10)	C7a—C8a—C9a—C3a	176.7 (6)
C8a—O1a—C1a—H1a	−178.1	C7a—C8a—C9a—C4a	−3.2 (10)
C1b—O1b—C8b—C7b	180.0 (6)	O1b—C1b—C2b—C3b	−2.9 (11)
C1b—O1b—C8b—C9b	0.3 (9)	O1b—C1b—C2b—C10b	176.3 (6)
C8b—O1b—C1b—C2b	2.5 (10)	H1b—C1b—C2b—C3b	177.1
C8b—O1b—C1b—H1b	−177.5	H1b—C1b—C2b—C10b	−3.7
O1a—C1a—C2a—C3a	−1.0 (11)	C1b—C2b—C3b—O2b	178.7 (7)
O1a—C1a—C2a—C10a	178.3 (6)	C1b—C2b—C3b—C9b	0.7 (10)
H1a—C1a—C2a—C3a	179.0	C1b—C2b—C10b—O3b	0.7 (11)
H1a—C1a—C2a—C10a	−1.7	C1b—C2b—C10b—H4b	−179.3
C1a—C2a—C3a—O2a	178.4 (7)	C3b—C2b—C10b—O3b	179.9 (7)
C1a—C2a—C3a—C9a	−1.1 (10)	C3b—C2b—C10b—H4b	−0.1
C1a—C2a—C10a—O3a	−2.4 (11)	C10b—C2b—C3b—O2b	−0.4 (11)
C1a—C2a—C10a—H4a	177.6	C10b—C2b—C3b—C9b	−178.5 (6)
C3a—C2a—C10a—O3a	176.9 (7)	O2b—C3b—C9b—C4b	4.2 (11)
C3a—C2a—C10a—H4a	−3.1	O2b—C3b—C9b—C8b	−176.2 (6)
C10a—C2a—C3a—O2a	−0.9 (11)	C2b—C3b—C9b—C4b	−177.7 (6)
C10a—C2a—C3a—C9a	179.7 (6)	C2b—C3b—C9b—C8b	1.8 (9)
O2a—C3a—C9a—C4a	2.6 (11)	C5b—C4b—C9b—C3b	−177.7 (6)
O2a—C3a—C9a—C8a	−177.3 (6)	C5b—C4b—C9b—C8b	2.7 (10)
C2a—C3a—C9a—C4a	−178.0 (6)	C9b—C4b—C5b—Cl1b	178.8 (6)
C2a—C3a—C9a—C8a	2.2 (10)	C9b—C4b—C5b—C6b	−0.9 (11)
C5a—C4a—C9a—C3a	−179.4 (6)	H2b—C4b—C5b—Cl1b	−1.2
C5a—C4a—C9a—C8a	0.5 (11)	H2b—C4b—C5b—C6b	179.1
C9a—C4a—C5a—Cl1a	−177.7 (6)	H2b—C4b—C9b—C3b	2.3
C9a—C4a—C5a—C6a	2.5 (11)	H2b—C4b—C9b—C8b	−177.3
H2a—C4a—C5a—Cl1a	2.3	Cl1b—C5b—C6b—C7b	179.0 (5)
H2a—C4a—C5a—C6a	−177.5	Cl1b—C5b—C6b—H3b	−1.0
H2a—C4a—C9a—C3a	0.6	C4b—C5b—C6b—C7b	−1.3 (11)
H2a—C4a—C9a—C8a	−179.5	C4b—C5b—C6b—H3b	178.6
Cl1a—C5a—C6a—C7a	177.5 (5)	C5b—C6b—C7b—Cl2b	−179.1 (6)
Cl1a—C5a—C6a—H3a	−2.5	C5b—C6b—C7b—C8b	1.6 (11)
C4a—C5a—C6a—C7a	−2.7 (11)	H3b—C6b—C7b—Cl2b	0.9
C4a—C5a—C6a—H3a	177.3	H3b—C6b—C7b—C8b	−178.4
C5a—C6a—C7a—Cl2a	−178.6 (6)	Cl2b—C7b—C8b—O1b	1.3 (9)
C5a—C6a—C7a—C8a	−0.1 (10)	Cl2b—C7b—C8b—C9b	−179.0 (5)
H3a—C6a—C7a—Cl2a	1.4	C6b—C7b—C8b—O1b	−179.3 (6)
H3a—C6a—C7a—C8a	179.9	C6b—C7b—C8b—C9b	0.3 (11)
Cl2a—C7a—C8a—O1a	−0.3 (9)	O1b—C8b—C9b—C3b	−2.4 (10)
Cl2a—C7a—C8a—C9a	−178.5 (5)	O1b—C8b—C9b—C4b	177.2 (6)
C6a—C7a—C8a—O1a	−178.8 (6)	C7b—C8b—C9b—C3b	178.0 (6)
C6a—C7a—C8a—C9a	3.0 (10)	C7b—C8b—C9b—C4b	−2.5 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C4bi—H2bi···O2a	0.95	2.35	3.246 (8)	157
C4a—H2a···O2bi	0.95	2.35	3.259 (8)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4b i—H2b i⋯O2a	0.95	2.35	3.246 (8)	157
C4a—H2a⋯O2b i	0.95	2.35	3.259 (8)	160

Symmetry code: (i) .