8-Chloro-4-oxo-4H-chromene-3-carbaldehyde

Ishikawa, Y.

doi:10.1107/S1600536814012483

organic compounds

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Volume 70| Part 7| July 2014| Page o743

https://doi.org/10.1107/S1600536814012483

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8-Chloro-4-oxo-4H-chromene-3-carbaldehyde

Yoshinobu Ishikawa ^a ^*

^aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
^*Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp

(Received 28 May 2014; accepted 28 May 2014; online 4 June 2014)

In the title compound, C₁₀H₅ClO₃, a chlorinated 3-formylchromone derivative, all atoms are essentially coplanar (r.m.s. deviation = 0.032 Å for the non-H atoms), with the largest deviation from the least-squares plane [0.0598 (14) Å] being for a pyran-ring C atom. In the crystal, molecules are linked through stacking interactions along the b axis [shortest centroid–centroid distance between the pyran and benzene rings = 3.566 (2) Å].

Related literature

For related structures, see: Ishikawa & Motohashi (2013 ); Ishikawa (2014 ). For the synthesis of the precursor of the title compound, see: Fumagalli et al. (2012 ). For van der Waals radii; see: Bondi (1964 ). For halogen bonding, see: Auffinger et al. (2004 ); Metrangolo et al. (2005 ); Wilcken et al. (2013 ); Sirimulla et al. (2013 ).

Experimental

Crystal data

C₁₀H₅ClO₃
M_r = 208.60
Triclinic, $[P \overline 1]$
a = 6.9436 (15) Å
b = 7.1539 (17) Å
c = 9.165 (2) Å
α = 102.049 (19)°
β = 103.403 (17)°
γ = 100.650 (19)°
V = 419.89 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 100 K
0.38 × 0.25 × 0.10 mm

Data collection

Rigaku AFC-7R diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.902, T_max = 0.958
2376 measured reflections
1932 independent reflections
1750 reflections with F² > 2σ(F²)
R_int = 0.011
3 standard reflections every 150 reflections intensity decay: −0.039%

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.075
S = 1.09
1932 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999 $[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]$ ); cell refinement: WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: SIR2008 (Burla et al., 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: CrystalStructure (Rigaku, 2010 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks General, I. DOI: https://doi.org/10.1107/S1600536814012483/zl2591sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814012483/zl2591Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814012483/zl2591Isup3.cml

checkCIF report

Comment top

Halogen bonds have been found to occur in organic, inorganic, and biological systems, and have recently attracted much attention in medicinal chemistry, chemical biology and supramolecular chemistry (Auffinger et al., 2004, Metrangolo et al., 2005, Wilcken et al., 2013, Sirimulla et al., 2013). We have recently reported the crystal structures of chlorinated 3-formylchromone derivatives 6,8-dichloro-4-oxochromene-3-carbaldehyde (Ishikawa & Motohashi, 2013, Fig.2 (top)) and 6-chloro-4-oxo-4H-chromene-3-carbaldehyde (Ishikawa, 2014, Fig.2 (middle)). It was found that a halogen bond is formed for 6,8-dichloro-4-oxochromene-3-carbaldehyde between the formyl oxygen atom and the chlorine atom at the 8-position, but none is formed for 6-chloro-4-oxo-4H-chromene-3-carbaldehyde between the formyl oxygen atom and the chlorine atom at the 6-position. As part of our interest in this type of chemical bonding, we herein report the crystal structure of a monochlorinated 3-formylchromone derivative 8-chloro-4-oxo-4H-chromene-3-carbaldehyde. The objective of this study is to reveal whether halogen bond(s) can be formed in the crystal of the title compound with the chlorine atom at 8-position and without a halogen atom at 6-position.

The mean deviation of the least-square planes for the non-hydrogen atoms is 0.0316 Å, and the largest deviation is 0.0598 (14) Å for C1. These mean that these atoms are essentially coplanar. In the crystal, the molecules are stacked with their inversion-symmetry equivalent along the b-axis direction [centroid–centroid distance between the pyran and benzene rings of the 4H-chromene units = 3.566 (2) Å, symmetry operator i: -x + 1, -y + 1, -z + 2], as shown in Fig.1.

The distance between the chlorine atom and the formyl oxygen atom of the translation-symmetry equivalent [Cl1···O3ⁱⁱ = 3.301 (2) Å, ii: x, y, z + 2] is nearly equal to the sum of their van der Waals radii [3.27 Å] (Bondi, 1964), as shown at the bottom of Fig.2. Thus, it is concluded that there is no halogen bond in the title compound. On the other hand, the angles of C–Cl···O (157.15 (6)°) and Cl···O=C (129.24 (10)°) are close to those of 6,8-dichloro-4-oxochromene-3-carbaldehyde, (C–Cl···O (160.4 (3)°) and Cl···O=C (138.7 (4)°), Fig.2(top)). Thus, the significance of the vicinal electron-withdrawing substituent in forming of a halogen bond (Wilcken et al., 2013) is crystallographically validated from the fact that halogen bonding is observed in the dichlorinated 3-formylchromone, but is not observed in the monochlorinated ones. These results should be invaluable for rational drug design.

Related literature top

For related structures, see: Ishikawa & Motohashi (2013); Ishikawa (2014). For the synthesis of the precursor of the title compound, see: Fumagalli et al. (2012). For van der Waals radii; see: Bondi (1964). For halogen bonding, see: Auffinger et al. (2004); Metrangolo et al. (2005); Wilcken et al. (2013); Sirimulla et al. (2013).

Experimental top

2-Hydroxy-3-chloroacetophenone was prepared according to a literature method (Fumagalli et al., 2012). To a solution of 2-hydroxy-3-chloroacetophenone (11.1 mmol) in N,N-dimethylformamide (30 ml) was added dropwise POCl₃ (27.7 mmol) for 5 min at 0 °C. After the mixture was stirred for 16 h at room temperature, water (50 ml) was added. The precipitates were collected, washed with water, and dried in vacuo (yield: 72%). ¹H NMR (400 MHz, DMSO-d₆): δ = 7.58 (t, 1H, J = 7.8 Hz), 8.07 (d, 1H, J = 7.8 Hz), 8.10 (d, 1H, J = 7.8 Hz), 9.03 (s, 1H), 10.12 (s, 1H). DART-MS calcd for [C₁₀H₅Cl₁O₃ + H⁺]: 209.001, found 209.014. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a chloroform solution of the title compound at room temperature.

Structure description top

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software (Rigaku, 1999); data reduction: WinAFC Diffractometer Control Software (Rigaku, 1999); program(s) used to solve structure: SIR2008 (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top

	Fig. 1. A packing view of the title compound, with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as small spheres of arbitrary radius.
	Fig. 2. Sphere models of the crystal structures of 6,8-dichloro-4-oxochromene-3-carbaldehyde (top), 6-chloro-4-oxo-4H-chromene-3-carbaldehyde (middle), and the title compound (bottom).

8-Chloro-4-oxo-4H-chromene-3-carbaldehyde top

Crystal data top

C₁₀H₅ClO₃	Z = 2
M_r = 208.60	F(000) = 212.00
Triclinic, P1	D_x = 1.650 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 6.9436 (15) Å	Cell parameters from 25 reflections
b = 7.1539 (17) Å	θ = 15.1–17.5°
c = 9.165 (2) Å	µ = 0.43 mm⁻¹
α = 102.049 (19)°	T = 100 K
β = 103.403 (17)°	Plate, yellow
γ = 100.650 (19)°	0.38 × 0.25 × 0.10 mm
V = 419.89 (18) Å³

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.011
ω–2θ scans	θ_max = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −5→9
T_min = 0.902, T_max = 0.958	k = −9→9
2376 measured reflections	l = −11→11
1932 independent reflections	3 standard reflections every 150 reflections
1750 reflections with F² > 2σ(F²)	intensity decay: −0.039%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0344P)² + 0.1939P] where P = (F_o² + 2F_c²)/3
1932 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₀H₅ClO₃	γ = 100.650 (19)°
M_r = 208.60	V = 419.89 (18) Å³
Triclinic, P1	Z = 2
a = 6.9436 (15) Å	Mo Kα radiation
b = 7.1539 (17) Å	µ = 0.43 mm⁻¹
c = 9.165 (2) Å	T = 100 K
α = 102.049 (19)°	0.38 × 0.25 × 0.10 mm
β = 103.403 (17)°

Data collection top

Rigaku AFC-7R diffractometer	1750 reflections with F² > 2σ(F²)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.011
T_min = 0.902, T_max = 0.958	3 standard reflections every 150 reflections
2376 measured reflections	intensity decay: −0.039%
1932 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.09	Δρ_max = 0.34 e Å⁻³
1932 reflections	Δρ_min = −0.26 e Å⁻³
127 parameters

Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.28721 (5)	0.37563 (5)	1.29528 (4)	0.02580 (11)
O1	0.21886 (13)	0.15266 (13)	0.97744 (10)	0.0187 (2)
O2	0.63950 (15)	0.10011 (16)	0.73295 (11)	0.0279 (3)
O3	0.04173 (16)	−0.20711 (16)	0.52591 (12)	0.0297 (3)
C1	0.16551 (19)	0.04262 (19)	0.82917 (14)	0.0189 (3)
C2	0.29522 (19)	0.01959 (19)	0.74169 (14)	0.0184 (3)
C3	0.51287 (19)	0.11867 (19)	0.80487 (14)	0.0184 (3)
C4	0.76947 (18)	0.35541 (19)	1.04110 (15)	0.0180 (3)
C5	0.81834 (19)	0.47543 (19)	1.19027 (15)	0.0189 (3)
C6	0.66911 (19)	0.48195 (18)	1.26931 (14)	0.0183 (3)
C7	0.47153 (19)	0.37036 (19)	1.19772 (14)	0.0176 (3)
C8	0.56861 (18)	0.24423 (18)	0.96597 (14)	0.0161 (3)
C9	0.41997 (18)	0.25375 (17)	1.04458 (14)	0.0157 (3)
C10	0.2152 (2)	−0.1091 (2)	0.58050 (15)	0.0236 (3)
H1	0.0257	−0.0238	0.7828	0.0227*
H2	0.8725	0.3481	0.9891	0.0216*
H3	0.3054	−0.1145	0.5169	0.0284*
H4	0.9536	0.5537	1.2392	0.0226*
H5	0.7035	0.5632	1.3724	0.0220*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01652 (16)	0.0338 (2)	0.02036 (17)	−0.00018 (12)	0.00735 (12)	−0.00404 (13)
O1	0.0116 (4)	0.0215 (5)	0.0159 (5)	−0.0032 (4)	0.0015 (4)	−0.0009 (4)
O2	0.0227 (5)	0.0370 (6)	0.0190 (5)	−0.0015 (5)	0.0093 (4)	0.0010 (4)
O3	0.0252 (6)	0.0309 (6)	0.0200 (5)	−0.0059 (5)	0.0003 (4)	−0.0027 (4)
C1	0.0158 (6)	0.0182 (6)	0.0159 (6)	−0.0030 (5)	−0.0003 (5)	0.0014 (5)
C2	0.0187 (6)	0.0174 (6)	0.0138 (6)	−0.0019 (5)	0.0009 (5)	0.0026 (5)
C3	0.0182 (6)	0.0197 (6)	0.0144 (6)	−0.0004 (5)	0.0032 (5)	0.0041 (5)
C4	0.0134 (6)	0.0200 (6)	0.0183 (6)	−0.0005 (5)	0.0038 (5)	0.0047 (5)
C5	0.0132 (6)	0.0200 (6)	0.0185 (6)	−0.0012 (5)	0.0004 (5)	0.0039 (5)
C6	0.0173 (6)	0.0177 (6)	0.0147 (6)	0.0006 (5)	0.0005 (5)	0.0006 (5)
C7	0.0147 (6)	0.0196 (6)	0.0165 (6)	0.0019 (5)	0.0044 (5)	0.0026 (5)
C8	0.0147 (6)	0.0169 (6)	0.0140 (6)	−0.0002 (5)	0.0025 (5)	0.0039 (5)
C9	0.0116 (6)	0.0154 (6)	0.0157 (6)	−0.0011 (5)	0.0004 (5)	0.0026 (5)
C10	0.0248 (7)	0.0257 (7)	0.0138 (6)	−0.0017 (6)	0.0024 (5)	0.0014 (5)

Geometric parameters (Å, º) top

Cl1—C7	1.7243 (16)	C4—C8	1.4029 (16)
O1—C1	1.3475 (15)	C5—C6	1.397 (2)
O1—C9	1.3763 (14)	C6—C7	1.3817 (17)
O2—C3	1.2250 (19)	C7—C9	1.4006 (17)
O3—C10	1.2061 (16)	C8—C9	1.393 (2)
C1—C2	1.347 (2)	C1—H1	0.950
C2—C3	1.4658 (17)	C4—H2	0.950
C2—C10	1.4836 (17)	C5—H4	0.950
C3—C8	1.4797 (17)	C6—H5	0.950
C4—C5	1.3815 (18)	C10—H3	0.950

Cl1···O1	2.8973 (12)	C3···H1	3.2929
O1···C3	2.8719 (19)	C3···H2	2.6746
O2···C1	3.574 (2)	C3···H3	2.7084
O2···C4	2.8604 (17)	C4···H5	3.2636
O2···C10	2.9089 (18)	C6···H2	3.2648
O3···C1	2.8120 (17)	C7···H4	3.2634
C1···C7	3.5981 (19)	C8···H4	3.2730
C1···C8	2.7591 (18)	C9···H1	3.1860
C2···C9	2.7695 (18)	C9···H2	3.2689
C4···C7	2.783 (2)	C9···H5	3.2672
C5···C9	2.7806 (18)	C10···H1	2.5482
C6···C8	2.7921 (18)	H1···H3	3.4825
Cl1···O2ⁱ	3.4989 (15)	H2···H4	2.3282
Cl1···O3ⁱⁱ	3.3012 (15)	H4···H5	2.3459
Cl1···C5ⁱⁱⁱ	3.4247 (16)	Cl1···H1ⁱⁱ	2.8415
O1···O1ⁱⁱ	3.5617 (16)	Cl1···H2ⁱⁱⁱ	3.4669
O1···O2ⁱ	3.5683 (17)	Cl1···H4ⁱⁱⁱ	2.8395
O1···C3ⁱ	3.5282 (19)	Cl1···H5^x	2.9688
O1···C4^iv	3.5456 (19)	O1···H1ⁱⁱ	3.2499
O1···C5^iv	3.359 (2)	O1···H2ⁱⁱⁱ	3.0086
O1···C8ⁱ	3.5096 (19)	O1···H4^iv	3.3704
O2···Cl1ⁱ	3.4989 (15)	O2···H1^viii	2.9439
O2···O1ⁱ	3.5683 (17)	O2···H3^v	2.4269
O2···C7ⁱ	3.534 (2)	O2···H4^xi	3.3161
O2···C9ⁱ	3.591 (2)	O3···H1^vi	3.5460
O2···C10^v	3.267 (2)	O3···H4^vii	2.6830
O3···Cl1ⁱⁱ	3.3012 (15)	O3···H5^vii	2.5041
O3···O3^vi	3.2307 (19)	O3···H5ⁱ	3.5184
O3···C5^vii	3.2551 (18)	C1···H2ⁱⁱⁱ	3.5714
O3···C6^vii	3.1687 (17)	C1···H2ⁱ	3.5400
O3···C6ⁱ	3.560 (2)	C1···H4^iv	3.2889
O3···C10^vi	3.295 (2)	C2···H5^iv	3.3614
C1···C4ⁱ	3.371 (3)	C3···H3^v	3.4629
C1···C5^iv	3.472 (3)	C3···H5^iv	3.4282
C1···C8ⁱ	3.542 (3)	C4···H1ⁱ	3.4694
C2···C6^iv	3.553 (3)	C4···H2^xi	3.0614
C2···C7ⁱ	3.552 (3)	C5···H2^xi	3.2259
C2···C9ⁱ	3.578 (2)	C6···H3ⁱ	3.5976
C3···O1ⁱ	3.5282 (19)	C10···H4^vii	3.3912
C3···C6^iv	3.460 (3)	C10···H5ⁱ	3.4945
C3···C7ⁱ	3.515 (3)	H1···Cl1ⁱⁱ	2.8415
C3···C9ⁱ	3.304 (3)	H1···O1ⁱⁱ	3.2499
C4···O1^iv	3.5456 (19)	H1···O2ⁱⁱⁱ	2.9439
C4···C1ⁱ	3.371 (3)	H1···O3^vi	3.5460
C4···C7^iv	3.570 (3)	H1···C4ⁱ	3.4694
C4···C9^iv	3.459 (3)	H1···H2ⁱⁱⁱ	3.4159
C5···Cl1^viii	3.4247 (16)	H1···H2ⁱ	3.4928
C5···O1^iv	3.359 (2)	H1···H3^vi	3.5853
C5···O3^ix	3.2551 (18)	H1···H4^iv	3.3899
C5···C1^iv	3.472 (3)	H2···Cl1^viii	3.4669
C5···C9^iv	3.521 (2)	H2···O1^viii	3.0086
C6···O3^ix	3.1687 (17)	H2···C1^viii	3.5714
C6···O3ⁱ	3.560 (2)	H2···C1ⁱ	3.5400
C6···C2^iv	3.553 (3)	H2···C4^xi	3.0614
C6···C3^iv	3.460 (3)	H2···C5^xi	3.2259
C6···C8^iv	3.538 (2)	H2···H1^viii	3.4159
C6···C10ⁱ	3.387 (3)	H2···H1ⁱ	3.4928
C7···O2ⁱ	3.534 (2)	H2···H2^xi	2.4762
C7···C2ⁱ	3.552 (3)	H2···H4^xi	2.7931
C7···C3ⁱ	3.515 (3)	H3···O2^v	2.4269
C7···C4^iv	3.570 (3)	H3···C3^v	3.4629
C7···C8^iv	3.427 (3)	H3···C6ⁱ	3.5976
C8···O1ⁱ	3.5096 (19)	H3···H1^vi	3.5853
C8···C1ⁱ	3.542 (3)	H3···H3^v	3.0081
C8···C6^iv	3.538 (2)	H3···H4^vii	3.2450
C8···C7^iv	3.427 (3)	H3···H5ⁱ	3.5572
C8···C9ⁱ	3.560 (2)	H4···Cl1^viii	2.8395
C8···C9^iv	3.600 (2)	H4···O1^iv	3.3704
C9···O2ⁱ	3.591 (2)	H4···O2^xi	3.3161
C9···C2ⁱ	3.578 (2)	H4···O3^ix	2.6830
C9···C3ⁱ	3.304 (3)	H4···C1^iv	3.2889
C9···C4^iv	3.459 (3)	H4···C10^ix	3.3912
C9···C5^iv	3.521 (2)	H4···H1^iv	3.3899
C9···C8ⁱ	3.560 (2)	H4···H2^xi	2.7931
C9···C8^iv	3.600 (2)	H4···H3^ix	3.2450
C10···O2^v	3.267 (2)	H5···Cl1^x	2.9688
C10···O3^vi	3.295 (2)	H5···O3^ix	2.5041
C10···C6ⁱ	3.387 (3)	H5···O3ⁱ	3.5184
Cl1···H5	2.8072	H5···C2^iv	3.3614
O2···H2	2.5915	H5···C3^iv	3.4282
O2···H3	2.6355	H5···C10ⁱ	3.4945
O3···H1	2.4818	H5···H3ⁱ	3.5572
C1···H3	3.2782

C1—O1—C9	118.02 (11)	C4—C8—C9	119.19 (11)
O1—C1—C2	125.01 (11)	O1—C9—C7	117.14 (12)
C1—C2—C3	120.64 (11)	O1—C9—C8	122.57 (10)
C1—C2—C10	119.09 (11)	C7—C9—C8	120.29 (11)
C3—C2—C10	120.26 (13)	O3—C10—C2	123.51 (15)
O2—C3—C2	123.90 (11)	O1—C1—H1	117.494
O2—C3—C8	122.20 (11)	C2—C1—H1	117.497
C2—C3—C8	113.90 (12)	C5—C4—H2	119.817
C5—C4—C8	120.37 (13)	C8—C4—H2	119.815
C4—C5—C6	120.11 (11)	C4—C5—H4	119.941
C5—C6—C7	120.09 (11)	C6—C5—H4	119.944
Cl1—C7—C6	120.35 (10)	C5—C6—H5	119.956
Cl1—C7—C9	119.75 (10)	C7—C6—H5	119.956
C6—C7—C9	119.90 (13)	O3—C10—H3	118.246
C3—C8—C4	121.00 (13)	C2—C10—H3	118.242
C3—C8—C9	119.81 (10)

C1—O1—C9—C7	178.77 (11)	C8—C4—C5—C6	2.1 (3)
C1—O1—C9—C8	−0.80 (18)	C8—C4—C5—H4	−177.9
C9—O1—C1—C2	1.7 (2)	H2—C4—C5—C6	−177.9
C9—O1—C1—H1	−178.3	H2—C4—C5—H4	2.1
O1—C1—C2—C3	−0.5 (3)	H2—C4—C8—C3	−1.5
O1—C1—C2—C10	179.02 (12)	H2—C4—C8—C9	178.9
H1—C1—C2—C3	179.5	C4—C5—C6—C7	−0.9 (2)
H1—C1—C2—C10	−1.0	C4—C5—C6—H5	179.1
C1—C2—C3—O2	178.13 (14)	H4—C5—C6—C7	179.1
C1—C2—C3—C8	−1.5 (2)	H4—C5—C6—H5	−0.9
C1—C2—C10—O3	−5.7 (3)	C5—C6—C7—Cl1	179.30 (12)
C1—C2—C10—H3	174.3	C5—C6—C7—C9	−1.3 (2)
C3—C2—C10—O3	173.77 (13)	H5—C6—C7—Cl1	−0.7
C3—C2—C10—H3	−6.2	H5—C6—C7—C9	178.7
C10—C2—C3—O2	−1.3 (3)	Cl1—C7—C9—O1	2.11 (18)
C10—C2—C3—C8	179.06 (12)	Cl1—C7—C9—C8	−178.31 (9)
O2—C3—C8—C4	3.0 (3)	C6—C7—C9—O1	−177.27 (12)
O2—C3—C8—C9	−177.39 (13)	C6—C7—C9—C8	2.3 (2)
C2—C3—C8—C4	−177.42 (12)	C3—C8—C9—O1	−1.2 (2)
C2—C3—C8—C9	2.21 (19)	C3—C8—C9—C7	179.27 (11)
C5—C4—C8—C3	178.54 (12)	C4—C8—C9—O1	178.46 (12)
C5—C4—C8—C9	−1.1 (2)	C4—C8—C9—C7	−1.1 (2)

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+2; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+2; (v) −x+1, −y, −z+1; (vi) −x, −y, −z+1; (vii) x−1, y−1, z−1; (viii) x+1, y, z; (ix) x+1, y+1, z+1; (x) −x+1, −y+1, −z+3; (xi) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₀H₅ClO₃
M_r	208.60
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.9436 (15), 7.1539 (17), 9.165 (2)
α, β, γ (°)	102.049 (19), 103.403 (17), 100.650 (19)
V (Å³)	419.89 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.38 × 0.25 × 0.10

Data collection
Diffractometer	Rigaku AFC-7R
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.902, 0.958
No. of measured, independent and observed [F² > 2σ(F²)] reflections	2376, 1932, 1750
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.075, 1.09
No. of reflections	1932
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.26

Computer programs: WinAFC Diffractometer Control Software (Rigaku, 1999), SIR2008 (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Acknowledgements

The University of Shizuoka is acknowledged for instrumental support.

References

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