6-Bromo-4-oxo-4H-chromene-3-carb­alde­hyde

Ishikawa, Y.

doi:10.1107/S160053681400796X

organic compounds

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Volume 70| Part 5| May 2014| Page o555

doi:10.1107/S160053681400796X

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6-Bromo-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 9 April 2014; accepted 9 April 2014; online 16 April 2014)

In the title compound, C₁₀H₅BrO₃, a brominated 3-formylchromone derivative, the non-H atoms are essentially coplanar (r.m.s. deviation = 0.0420 Å), with the largest deviation from its mean plane [0.109 (2) Å] being found for the ring-bound carbonyl O atom. In the crystal, molecules are linked through halogen bonds [Br⋯O = 3.191 (2) Å, C—Br⋯O = 167.32 (10)° and C=O⋯Br = 168.4 (2)°] along [101]. Molecules are assembled into layers parallel to (101) via π–π stacking interactions along the b axis [shortest centroid–centroid distance between the pyran and benzene rings = 3.495 (2) Å].

CCDC reference: 996416

Related literature

For related structures, see: Ishikawa & Motohashi (2013 ); Ishikawa (2014a ,b ). For halogen bonding, see: Auffinger et al. (2004 ); Metrangolo et al. (2005 ); Wilcken et al. (2013 ); Sirimulla et al. (2013 ).

Experimental

Crystal data

C₁₀H₅BrO₃
M_r = 253.05
Triclinic, $[P \overline 1]$
a = 6.5743 (18) Å
b = 6.967 (3) Å
c = 10.350 (4) Å
α = 71.02 (3)°
β = 85.53 (3)°
γ = 70.67 (3)°
V = 422.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 4.85 mm⁻¹
T = 100 K
0.42 × 0.40 × 0.38 mm

Data collection

Rigaku AFC-7R diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.135, T_max = 0.159
2389 measured reflections
1944 independent reflections
1880 reflections with F² > 2σ(F²)
R_int = 0.024
3 standard reflections every 150 reflections intensity decay: 2.0%

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.077
S = 1.16
1944 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 1.05 e Å⁻³
Δρ_min = −0.74 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: SIR92 (Altomare, et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: CrystalStructure (Rigaku, 2010 ); software used to prepare material for publication: CrystalStructure.

Supporting information

CCDC reference: 996416

Crystal structure: contains datablocks General, I. DOI: 10.1107/S160053681400796X/tk5306sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681400796X/tk5306Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681400796X/tk5306Isup3.cml

checkCIF report

Structural commentary 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 dihalogenated 3-formylchromone derivatives 6,8-dichloro-4-oxo-4H-chromene-3-carbaldehyde (Ishikawa & Motohashi, 2013, Fig.3 (top left)) and 6,8-dibromo-4-oxo-4H-chromene-3-carbaldehyde (Ishikawa, 2014a, Fig.3 (top right)). It was found that halogen bonds between the formyl oxygen atom and the halogen atoms at 8-position are formed in those crystals in a similar fashion. On the other hand, halogen bond is not observed between any oxygen atom and the chlorine atom at 6-position in the crystal structure of 6-chloro-4-oxo-4H-chromene-3-carbaldehyde (Ishikawa, 2014b, Fig.3 (bottom left)). As part of our interest in this type of chemical bonding, we herein report the crystal structure of a monobrominated 3-formylchromone derivative 6-bromo-4-oxo-4H-chromene-3-carbaldehyde. The objective of this study is to reveal whether halogen bond(s) can be formed in the crystal structure of the title compound with the bromine atom at 6-position and without a halogen atom at 8-position.

The mean deviation of the least-square planes for the non-hydrogen atoms is 0.0420 Å, and the largest deviation is 0.109 (2) Å for O2. These mean that these atoms are essentially coplanar (Fig.1).

In the crystal, the molecules are stacked with the inversion-symmetry equivalentⁱ along the b-axis direction [shortest centroid–centroid distance between the pyran and benzene rings of the 4H-chromene units = 3.495 (2) Å, i: -x + 1, -y + 1, -z + 1], as shown in Fig. 1. The Cg–Cg distance of the title compound is almost equal to that of 6-chloro-4-oxo-4H-chromene-3-carbaldehyde (3.4959 (15) Å, Ishikawa, 2014b).

Halogen bond was observed between the bromine atom at 6-position and the formyl oxygen atom of the translation-symmetry equivalentⁱⁱ [Br1···O3ⁱⁱ = 3.191 (2) Å, ii: x - 1, y, z + 1] along [101], as shown in Fig.2. The angles of C–Br···O and Br···O=C are 167.32 (10) and 168.4 (2)°, respectively. Thus, it is found that halogen bonds are formed for the bromine atoms not only at 8-position but also at 6-position, as shown in the top right and bottom right of Fig.3.

The space group and crystal packing mode of the title compound are the same with those of 6-chloro-4-oxo-4H-chromene-3-carbaldehyde. On the other hand, halogen bond is observed in the former and not in the latter, as shown in the bottom of Fig.3. These should be accounted for by the larger size of the σ hole of the bromine atom at 6-position (Wilcken et al., 2013). These results might be applicable for rational drug design.

Synthesis and crystallization top

Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an N,N-dimethylformamide solution of the commercially available title compound at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The C(sp²)-bound hydrogen atoms were placed in geometrical positions [C–H 0.95 Å, U_iso(H) = 1.2U_eq(C)], and refined using a riding model.

Related literature top

For related structures, see: Ishikawa & Motohashi (2013); Ishikawa (2014a,b). For halogen bonding, see: Auffinger et al. (2004); Metrangolo et al. (2005); Wilcken et al. (2013); Sirimulla et al. (2013).

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: SIR92 (Altomare, et al., 1994); 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. A packing view of the title compound. The intermolecular halogen bonds are represented as dashed lines for Br···O.
	Fig. 3. Sphere models of the crystal structures of 6,8-dichloro-4-oxo-4H-chromene-3-carbaldehyde (top left), 6,8-dibromo-4-oxo-4H-chromene-3-carbaldehyde (top right), 6-chloro-4-oxo-4H-chromene-3-carbaldehyde (bottom left), and the title compound (bottom right).

6-Bromo-4-oxo-4H-chromene-3-carbaldehyde top

Crystal data top

C₁₀H₅BrO₃	Z = 2
M_r = 253.05	F(000) = 248.00
Triclinic, P1	D_x = 1.988 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 6.5743 (18) Å	Cell parameters from 25 reflections
b = 6.967 (3) Å	θ = 15.2–17.4°
c = 10.350 (4) Å	µ = 4.85 mm⁻¹
α = 71.02 (3)°	T = 100 K
β = 85.53 (3)°	Block, colorless
γ = 70.67 (3)°	0.42 × 0.40 × 0.38 mm
V = 422.8 (3) Å³

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.024
ω–2θ scans	θ_max = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −8→8
T_min = 0.135, T_max = 0.159	k = −5→9
2389 measured reflections	l = −12→13
1944 independent reflections	3 standard reflections every 150 reflections
1880 reflections with F² > 2σ(F²)	intensity decay: 2.0%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0545P)² + 0.1959P] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max = 0.001
1944 reflections	Δρ_max = 1.05 e Å⁻³
128 parameters	Δρ_min = −0.74 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.151 (9)
Secondary atom site location: difference Fourier map

Crystal data top

C₁₀H₅BrO₃	γ = 70.67 (3)°
M_r = 253.05	V = 422.8 (3) Å³
Triclinic, P1	Z = 2
a = 6.5743 (18) Å	Mo Kα radiation
b = 6.967 (3) Å	µ = 4.85 mm⁻¹
c = 10.350 (4) Å	T = 100 K
α = 71.02 (3)°	0.42 × 0.40 × 0.38 mm
β = 85.53 (3)°

Data collection top

Rigaku AFC-7R diffractometer	1880 reflections with F² > 2σ(F²)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.024
T_min = 0.135, T_max = 0.159	3 standard reflections every 150 reflections
2389 measured reflections	intensity decay: 2.0%
1944 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.16	Δρ_max = 1.05 e Å⁻³
1944 reflections	Δρ_min = −0.74 e Å⁻³
128 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
Br1	0.09454 (3)	0.28528 (3)	0.922893 (19)	0.01450 (13)
O1	0.8085 (3)	0.1862 (3)	0.52565 (16)	0.0122 (3)
O2	0.1989 (3)	0.3151 (3)	0.38347 (17)	0.0157 (4)
O3	0.6969 (3)	0.2664 (3)	0.11860 (18)	0.0203 (4)
C1	0.7668 (4)	0.2190 (4)	0.3943 (3)	0.0120 (4)
C2	0.5687 (4)	0.2640 (3)	0.3402 (2)	0.0101 (4)
C3	0.3797 (4)	0.2830 (3)	0.4253 (2)	0.0100 (4)
C4	0.2621 (4)	0.2805 (3)	0.6624 (2)	0.0106 (4)
C5	0.3145 (4)	0.2506 (4)	0.7956 (3)	0.0112 (4)
C6	0.5287 (4)	0.1952 (4)	0.8394 (3)	0.0136 (4)
C7	0.6918 (4)	0.1709 (4)	0.7478 (3)	0.0132 (4)
C8	0.4269 (3)	0.2578 (4)	0.5684 (2)	0.0092 (4)
C9	0.6393 (4)	0.2048 (3)	0.6128 (3)	0.0107 (4)
C10	0.5462 (4)	0.2943 (4)	0.1932 (3)	0.0145 (4)
H1	0.8846	0.2100	0.3347	0.0143*
H2	0.1162	0.3159	0.6347	0.0127*
H3	0.5614	0.1744	0.9318	0.0163*
H4	0.8378	0.1315	0.7765	0.0158*
H5	0.4050	0.3382	0.1550	0.0174*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01323 (17)	0.01865 (17)	0.01105 (16)	−0.00255 (10)	0.00148 (9)	−0.00690 (10)
O1	0.0070 (7)	0.0168 (8)	0.0124 (8)	−0.0032 (6)	−0.0008 (6)	−0.0044 (6)
O2	0.0099 (7)	0.0254 (9)	0.0140 (8)	−0.0066 (6)	−0.0013 (6)	−0.0079 (7)
O3	0.0184 (8)	0.0302 (10)	0.0172 (9)	−0.0093 (7)	0.0048 (7)	−0.0133 (8)
C1	0.0107 (9)	0.0122 (9)	0.0133 (10)	−0.0034 (8)	0.0011 (8)	−0.0050 (8)
C2	0.0104 (9)	0.0089 (9)	0.0120 (10)	−0.0032 (7)	−0.0000 (8)	−0.0045 (7)
C3	0.0103 (9)	0.0085 (9)	0.0118 (10)	−0.0032 (7)	−0.0012 (8)	−0.0037 (7)
C4	0.0095 (9)	0.0104 (9)	0.0126 (10)	−0.0032 (7)	−0.0001 (8)	−0.0047 (8)
C5	0.0122 (9)	0.0110 (9)	0.0116 (10)	−0.0040 (7)	0.0019 (8)	−0.0055 (7)
C6	0.0154 (10)	0.0122 (10)	0.0139 (10)	−0.0045 (8)	−0.0037 (8)	−0.0043 (8)
C7	0.0107 (9)	0.0144 (10)	0.0143 (11)	−0.0041 (8)	−0.0038 (8)	−0.0035 (8)
C8	0.0087 (9)	0.0085 (8)	0.0117 (10)	−0.0035 (7)	0.0001 (8)	−0.0043 (7)
C9	0.0095 (9)	0.0088 (9)	0.0135 (10)	−0.0032 (7)	0.0004 (8)	−0.0032 (7)
C10	0.0153 (10)	0.0174 (10)	0.0139 (10)	−0.0069 (8)	0.0005 (8)	−0.0075 (8)

Geometric parameters (Å, º) top

Br1—C5	1.888 (3)	C4—C8	1.403 (3)
O1—C1	1.338 (3)	C5—C6	1.401 (4)
O1—C9	1.375 (3)	C6—C7	1.380 (4)
O2—C3	1.221 (3)	C7—C9	1.391 (4)
O3—C10	1.211 (3)	C8—C9	1.395 (3)
C1—C2	1.356 (4)	C1—H1	0.950
C2—C3	1.461 (3)	C4—H2	0.950
C2—C10	1.478 (4)	C6—H3	0.950
C3—C8	1.480 (4)	C7—H4	0.950
C4—C5	1.379 (4)	C10—H5	0.950

O1···C3	2.868 (3)	C9···H1	3.1828
O2···C1	3.572 (3)	C9···H2	3.2719
O2···C4	2.869 (3)	C9···H3	3.2502
O2···C10	2.894 (3)	C10···H1	2.5537
O3···C1	2.820 (4)	H1···H5	3.4881
C1···C7	3.574 (4)	H3···H4	2.3392
C1···C8	2.757 (3)	Br1···H3^xi	3.1998
C2···C9	2.768 (4)	Br1···H4^vi	2.9904
C4···C7	2.805 (4)	Br1···H4^xi	3.4343
C5···C9	2.748 (4)	Br1···H5^x	3.4515
C6···C8	2.795 (4)	Br1···H5^vii	3.4131
Br1···O3ⁱ	3.191 (2)	O1···H1ⁱⁱ	2.8201
O1···O1ⁱⁱ	3.117 (3)	O1···H2ⁱⁱⁱ	2.9005
O1···O2ⁱⁱⁱ	3.104 (3)	O1···H2^v	3.5064
O1···O2^iv	3.325 (3)	O2···H1^vi	2.5430
O1···C1ⁱⁱ	3.174 (3)	O2···H2^vii	2.6756
O1···C4^v	3.479 (3)	O3···H3^ix	2.5290
O1···C8^v	3.488 (3)	O3···H3^v	3.5734
O2···O1^vi	3.104 (3)	O3···H4ⁱⁱ	3.3419
O2···O1^iv	3.325 (3)	O3···H5^xii	3.1712
O2···C1^vi	3.113 (4)	C1···H2^v	3.4876
O2···C4^vii	3.325 (3)	C3···H2^vii	3.4612
O2···C9^iv	3.408 (4)	C4···H1^v	3.3664
O3···Br1^viii	3.191 (2)	C4···H4^vi	3.2949
O3···C5^iv	3.444 (4)	C5···H1^v	3.3731
O3···C6^ix	3.408 (4)	C5···H3^xi	3.2745
C1···O1ⁱⁱ	3.174 (3)	C5···H4^vi	3.5319
C1···O2ⁱⁱⁱ	3.113 (4)	C6···H3^xi	3.0684
C1···C4^v	3.285 (4)	C6···H5^iv	3.5775
C1···C5^v	3.455 (4)	C6···H5^v	3.4388
C1···C8^v	3.581 (4)	C7···H1ⁱⁱ	3.4259
C2···C4^iv	3.591 (4)	C7···H2ⁱⁱⁱ	3.2813
C2···C5^v	3.530 (4)	C9···H1ⁱⁱ	3.4206
C2···C6^v	3.478 (4)	C9···H2ⁱⁱⁱ	3.5095
C2···C7^v	3.566 (4)	C10···H3^ix	3.0662
C2···C8^iv	3.437 (4)	C10···H3^v	3.3423
C3···C3^iv	3.568 (3)	H1···O1ⁱⁱ	2.8201
C3···C7^v	3.525 (4)	H1···O2ⁱⁱⁱ	2.5430
C3···C8^iv	3.535 (4)	H1···C4^v	3.3664
C3···C9^iv	3.588 (4)	H1···C5^v	3.3731
C3···C9^v	3.422 (4)	H1···C7ⁱⁱ	3.4259
C4···O1^v	3.479 (3)	H1···C9ⁱⁱ	3.4206
C4···O2^vii	3.325 (3)	H1···H2^iv	3.5756
C4···C1^v	3.285 (4)	H1···H2^v	3.4176
C4···C2^iv	3.591 (4)	H1···H4ⁱⁱ	2.9827
C4···C10^iv	3.594 (4)	H2···O1^vi	2.9005
C5···O3^iv	3.444 (4)	H2···O1^v	3.5064
C5···C1^v	3.455 (4)	H2···O2^vii	2.6756
C5···C2^v	3.530 (4)	H2···C1^v	3.4876
C5···C10^iv	3.563 (4)	H2···C3^vii	3.4612
C6···O3^x	3.408 (4)	H2···C7^vi	3.2813
C6···C2^v	3.478 (4)	H2···C9^vi	3.5095
C6···C10^v	3.331 (4)	H2···H1^iv	3.5756
C7···C2^v	3.566 (4)	H2···H1^v	3.4176
C7···C3^v	3.525 (4)	H2···H2^vii	3.1789
C8···O1^v	3.488 (3)	H2···H4^vi	2.6584
C8···C1^v	3.581 (4)	H3···Br1^xi	3.1998
C8···C2^iv	3.437 (4)	H3···O3^x	2.5290
C8···C3^iv	3.535 (4)	H3···O3^v	3.5734
C8···C9^v	3.494 (4)	H3···C5^xi	3.2745
C9···O2^iv	3.408 (4)	H3···C6^xi	3.0684
C9···C3^iv	3.588 (4)	H3···C10^x	3.0662
C9···C3^v	3.422 (4)	H3···C10^v	3.3423
C9···C8^v	3.494 (4)	H3···H3^xi	2.7283
C10···C4^iv	3.594 (4)	H3···H5^x	2.8751
C10···C5^iv	3.563 (4)	H3···H5^v	3.2964
C10···C6^v	3.331 (4)	H4···Br1ⁱⁱⁱ	2.9904
Br1···H2	2.9161	H4···Br1^xi	3.4343
Br1···H3	2.9076	H4···O3ⁱⁱ	3.3419
O1···H4	2.5120	H4···C4ⁱⁱⁱ	3.2949
O2···H2	2.6160	H4···C5ⁱⁱⁱ	3.5319
O2···H5	2.6169	H4···H1ⁱⁱ	2.9827
O3···H1	2.4933	H4···H2ⁱⁱⁱ	2.6584
C1···H5	3.2796	H5···Br1^ix	3.4515
C3···H1	3.2958	H5···Br1^vii	3.4131
C3···H2	2.6880	H5···O3^xii	3.1712
C3···H5	2.6959	H5···C6^iv	3.5775
C4···H3	3.2780	H5···C6^v	3.4388
C5···H4	3.2671	H5···H3^ix	2.8751
C6···H2	3.2828	H5···H3^v	3.2964
C8···H4	3.2883

C1—O1—C9	118.51 (18)	C4—C8—C9	118.9 (2)
O1—C1—C2	124.7 (2)	O1—C9—C7	116.04 (19)
C1—C2—C3	120.7 (2)	O1—C9—C8	122.2 (2)
C1—C2—C10	119.0 (2)	C7—C9—C8	121.7 (2)
C3—C2—C10	120.3 (2)	O3—C10—C2	124.0 (3)
O2—C3—C2	123.6 (3)	O1—C1—H1	117.637
O2—C3—C8	122.6 (2)	C2—C1—H1	117.636
C2—C3—C8	113.81 (19)	C5—C4—H2	120.442
C5—C4—C8	119.1 (2)	C8—C4—H2	120.436
Br1—C5—C4	119.78 (16)	C5—C6—H3	120.165
Br1—C5—C6	118.71 (18)	C7—C6—H3	120.161
C4—C5—C6	121.5 (2)	C6—C7—H4	120.488
C5—C6—C7	119.7 (3)	C9—C7—H4	120.487
C6—C7—C9	119.0 (2)	O3—C10—H5	118.015
C3—C8—C4	121.2 (2)	C2—C10—H5	118.010
C3—C8—C9	119.87 (19)

C1—O1—C9—C7	−179.47 (17)	C8—C4—C5—Br1	178.91 (17)
C1—O1—C9—C8	−0.5 (3)	C8—C4—C5—C6	−1.0 (4)
C9—O1—C1—C2	−1.9 (3)	H2—C4—C5—Br1	−1.1
C9—O1—C1—H1	178.1	H2—C4—C5—C6	179.0
O1—C1—C2—C3	0.8 (4)	H2—C4—C8—C3	−1.5
O1—C1—C2—C10	−179.35 (18)	H2—C4—C8—C9	−179.7
H1—C1—C2—C3	−179.2	Br1—C5—C6—C7	−179.45 (14)
H1—C1—C2—C10	0.6	Br1—C5—C6—H3	0.6
C1—C2—C3—O2	−177.1 (2)	C4—C5—C6—C7	0.4 (4)
C1—C2—C3—C8	2.4 (3)	C4—C5—C6—H3	−179.6
C1—C2—C10—O3	5.5 (4)	C5—C6—C7—C9	0.8 (4)
C1—C2—C10—H5	−174.5	C5—C6—C7—H4	−179.2
C3—C2—C10—O3	−174.6 (2)	H3—C6—C7—C9	−179.2
C3—C2—C10—H5	5.4	H3—C6—C7—H4	0.8
C10—C2—C3—O2	3.0 (4)	C6—C7—C9—O1	177.51 (19)
C10—C2—C3—C8	−177.47 (18)	C6—C7—C9—C8	−1.5 (4)
O2—C3—C8—C4	−3.2 (4)	H4—C7—C9—O1	−2.5
O2—C3—C8—C9	174.99 (19)	H4—C7—C9—C8	178.5
C2—C3—C8—C4	177.26 (17)	C3—C8—C9—O1	3.8 (4)
C2—C3—C8—C9	−4.5 (3)	C3—C8—C9—C7	−177.29 (18)
C5—C4—C8—C3	178.50 (18)	C4—C8—C9—O1	−177.99 (18)
C5—C4—C8—C9	0.3 (3)	C4—C8—C9—C7	1.0 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₅BrO₃
M_r	253.05
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.5743 (18), 6.967 (3), 10.350 (4)
α, β, γ (°)	71.02 (3), 85.53 (3), 70.67 (3)
V (Å³)	422.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.85
Crystal size (mm)	0.42 × 0.40 × 0.38

Data collection
Diffractometer	Rigaku AFC-7R diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.135, 0.159
No. of measured, independent and observed [F² > 2σ(F²)] reflections	2389, 1944, 1880
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.077, 1.16
No. of reflections	1944
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.74

Computer programs: WinAFC Diffractometer Control Software (Rigaku, 1999), SIR92 (Altomare, et al., 1994), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Acknowledgements

The author acknowledges the University of Shizuoka for instrumental support.

References

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