6,8-Di-bromo-4-oxo-4H-chromene-3-carbaldehyde.

In the title compound, C10H4Br2O3, the atoms of the 6,8-di-bromo-chromone unit are essentially coplanar [largest deviation from the mean planes = 0.1109 (3) Å] and the formyl group is twisted slightly with respect to the attached ring [C-C-C-O torsion angles = 11.5 (4) and -168.9 (3)°]. In the crystal, mol-ecules are linked to each other through halogen bonds [Br⋯O = 3.118 (2) Å, C-Br⋯O = 162.37 (8) and C=O⋯Br = 140.20 (15)°]. The molecules are further assembled via π-π stacking interactions [centroid-centroid distance = 3.850 (2) Å].

Related literature

For the biological activity of the title compound, see: Kawase et al. (2007 ▶). For its use as a starting material for the synthesis of alkaline phosphatase inhibitorsrelated literature, see: al-Rashida et al. (2013 ▶). For a related structure, see: Ishikawa & Motohashi (2013 ▶). For halogen bonding, see: Auffinger et al. (2004 ▶); Metrangolo et al. (2005 ▶); Wilcken et al. (2013 ▶); Sirimulla et al. (2013 ▶).

Experimental

Crystal data

C10H4Br2O3

M = 331.95

Monoclinic,

a = 11.910 (4) Å

b = 3.8500 (12) Å

c = 20.817 (6) Å

β = 95.69 (3)°

V = 949.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 8.54 mm−1

T = 100 K

0.42 × 0.25 × 0.23 mm

Data collection

Rigaku AFC-7R diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.086, T max = 0.140

2871 measured reflections

2163 independent reflections

1937 reflections with F 2 > 2σ(F 2)

R int = 0.010

3 standard reflections every 150 reflections intensity decay: −0.1%

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.045

S = 1.06

2163 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.46 e Å−3

Data collection: WinAFC (Rigaku, 1999 ▶); cell refinement: WinAFC; data reduction: WinAFC; 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.

Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536814005327/rn2123sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005327/rn2123Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005327/rn2123Isup3.cml

CCDC reference: 990678

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H4Br2O3	F(000) = 632.00
Mr = 331.95	Dx = 2.321 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.910 (4) Å	θ = 15.0–17.3°
b = 3.8500 (12) Å	µ = 8.54 mm−1
c = 20.817 (6) Å	T = 100 K
β = 95.69 (3)°	Block, colorless
V = 949.8 (5) Å3	0.42 × 0.25 × 0.23 mm
Z = 4

Rigaku AFC-7R diffractometer	Rint = 0.010
ω scans	θmax = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = −15→15
Tmin = 0.086, Tmax = 0.140	k = −2→4
2871 measured reflections	l = −14→26
2163 independent reflections	3 standard reflections every 150 reflections
1937 reflections with F2 > 2σ(F2)	intensity decay: −0.1%

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.045	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0209P)2 + 0.9331P] where P = (Fo2 + 2Fc2)/3
2163 reflections	(Δ/σ)max = 0.002
136 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.46 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
Br1	0.573035 (18)	0.93086 (6)	0.699129 (10)	0.01429 (7)
Br2	0.985432 (18)	0.27016 (6)	0.660364 (10)	0.01402 (6)
O1	0.88801 (13)	0.2982 (5)	0.52224 (7)	0.0135 (4)
O2	0.59071 (14)	0.7059 (5)	0.43970 (8)	0.0183 (4)
O3	0.78264 (15)	0.1122 (6)	0.32871 (8)	0.0230 (4)
C1	0.85463 (19)	0.2641 (7)	0.45870 (10)	0.0137 (5)
C2	0.75650 (19)	0.3792 (7)	0.42904 (10)	0.0138 (5)
C3	0.67683 (19)	0.5722 (7)	0.46469 (10)	0.0132 (5)
C4	0.63812 (18)	0.7387 (6)	0.57688 (10)	0.0125 (5)
C5	0.67063 (18)	0.7382 (7)	0.64209 (10)	0.0122 (5)
C6	0.77314 (18)	0.5989 (7)	0.66820 (10)	0.0129 (5)
C7	0.84520 (18)	0.4570 (7)	0.62724 (10)	0.0123 (5)
C8	0.71085 (18)	0.5882 (7)	0.53541 (10)	0.0119 (5)
C9	0.81363 (18)	0.4500 (6)	0.56088 (10)	0.0111 (5)
C10	0.7291 (2)	0.3114 (7)	0.35894 (11)	0.0173 (5)
H1	0.9046	0.1492	0.4329	0.0165*
H4	0.5682	0.8381	0.5602	0.0149*
H6	0.7932	0.6016	0.7135	0.0155*
H10	0.6668	0.4296	0.3368	0.0208*

	U11	U22	U33	U12	U13	U23
Br1	0.01503 (11)	0.01571 (12)	0.01299 (11)	0.00054 (9)	0.00562 (8)	−0.00072 (9)
Br2	0.01206 (11)	0.01685 (12)	0.01260 (11)	0.00133 (9)	−0.00153 (8)	0.00018 (9)
O1	0.0109 (8)	0.0193 (9)	0.0102 (7)	0.0017 (7)	0.0008 (6)	−0.0015 (7)
O2	0.0151 (8)	0.0233 (10)	0.0159 (8)	0.0032 (8)	−0.0015 (7)	0.0023 (8)
O3	0.0206 (9)	0.0327 (11)	0.0157 (8)	0.0031 (9)	0.0015 (7)	−0.0066 (8)
C1	0.0151 (11)	0.0162 (12)	0.0099 (10)	−0.0017 (10)	0.0013 (8)	−0.0029 (9)
C2	0.0142 (11)	0.0145 (12)	0.0128 (11)	−0.0025 (10)	0.0013 (9)	−0.0005 (9)
C3	0.0142 (11)	0.0137 (12)	0.0117 (10)	−0.0038 (10)	0.0013 (8)	0.0008 (9)
C4	0.0107 (10)	0.0117 (12)	0.0148 (11)	−0.0015 (9)	0.0003 (8)	0.0009 (9)
C5	0.0121 (11)	0.0114 (12)	0.0141 (10)	−0.0025 (10)	0.0072 (8)	−0.0014 (9)
C6	0.0150 (11)	0.0135 (12)	0.0103 (10)	−0.0022 (10)	0.0013 (8)	0.0006 (9)
C7	0.0109 (10)	0.0123 (12)	0.0136 (11)	−0.0007 (9)	−0.0004 (8)	0.0012 (9)
C8	0.0114 (10)	0.0125 (12)	0.0119 (10)	−0.0029 (10)	0.0017 (8)	0.0012 (9)
C9	0.0108 (10)	0.0110 (11)	0.0122 (10)	−0.0008 (9)	0.0041 (8)	0.0002 (9)
C10	0.0157 (11)	0.0241 (14)	0.0117 (11)	−0.0008 (11)	−0.0006 (9)	−0.0006 (10)

Br1—C5	1.893 (3)	C4—C5	1.374 (3)
Br2—C7	1.885 (3)	C4—C8	1.407 (4)
O1—C1	1.349 (3)	C5—C6	1.394 (3)
O1—C9	1.384 (3)	C6—C7	1.381 (4)
O2—C3	1.217 (3)	C7—C9	1.395 (3)
O3—C10	1.213 (4)	C8—C9	1.391 (3)
C1—C2	1.342 (3)	C1—H1	0.950
C2—C3	1.464 (4)	C4—H4	0.950
C2—C10	1.486 (3)	C6—H6	0.950
C3—C8	1.489 (3)	C10—H10	0.950
Br2···O1	2.9940 (17)	C10···O2v	3.395 (4)
O1···C3	2.877 (3)	C10···O3iii	3.223 (4)
O2···C1	3.561 (3)	Br1···H4	2.9089
O2···C4	2.858 (3)	Br1···H6	2.9009
O2···C10	2.898 (4)	Br2···H6	2.9323
O3···C1	2.818 (3)	O2···H4	2.5993
C1···C7	3.599 (4)	O2···H10	2.6314
C1···C8	2.753 (4)	O3···H1	2.4918
C2···C9	2.775 (3)	C1···H10	3.2748
C4···C7	2.801 (3)	C3···H1	3.2875
C5···C9	2.750 (4)	C3···H4	2.6802
C6···C8	2.790 (3)	C3···H10	2.7091
Br1···Br1i	3.4567 (8)	C4···H6	3.2769
Br1···Br1ii	3.4567 (8)	C6···H4	3.2818
Br1···C5iii	3.563 (3)	C9···H1	3.1918
Br2···O3iv	3.118 (2)	C9···H4	3.2814
Br2···C7v	3.583 (3)	C9···H6	3.2634
O1···O1vi	3.298 (3)	C10···H1	2.5478
O1···C1vi	3.486 (3)	H1···H10	3.4736
O1···C8v	3.481 (3)	Br1···H10vii	3.1969
O1···C9v	3.498 (3)	Br1···H10xi	3.0191
O2···C2iii	3.280 (3)	Br2···H1iv	2.9314
O2···C3iii	3.513 (4)	Br2···H1vi	3.3140
O2···C4vii	3.208 (3)	Br2···H6xii	3.5908
O2···C4viii	3.455 (3)	O1···H1iv	3.0794
O2···C10iii	3.395 (4)	O1···H1vi	3.3226
O3···Br2iv	3.118 (2)	O2···H4vii	2.8234
O3···C2v	3.543 (4)	O2···H4viii	2.5820
O3···C6ix	3.430 (3)	O3···H6ix	2.5500
O3···C10v	3.223 (4)	O3···H10v	2.9808
C1···O1vi	3.486 (3)	C1···H1iii	3.5101
C1···C3v	3.413 (4)	C2···H1iii	3.4467
C1···C8v	3.577 (4)	C3···H4vii	3.3142
C2···O2v	3.280 (3)	C4···H4v	3.5744
C2···O3iii	3.543 (4)	C8···H4v	3.4152
C2···C3v	3.353 (4)	C10···H6ix	3.5682
C3···O2v	3.513 (4)	C10···H10v	3.4959
C3···C1iii	3.413 (4)	H1···Br2iv	2.9314
C3···C2iii	3.353 (4)	H1···Br2vi	3.3140
C4···O2vii	3.208 (3)	H1···O1iv	3.0794
C4···O2viii	3.455 (3)	H1···O1vi	3.3226
C4···C8iii	3.513 (4)	H1···C1v	3.5101
C4···C9iii	3.481 (4)	H1···C2v	3.4467
C5···Br1v	3.563 (3)	H4···O2vii	2.8234
C5···C6iii	3.555 (4)	H4···O2viii	2.5820
C5···C7iii	3.493 (4)	H4···C3vii	3.3142
C6···O3x	3.430 (3)	H4···C4iii	3.5744
C6···C5v	3.555 (4)	H4···C8iii	3.4152
C6···C7iii	3.539 (4)	H4···H4viii	3.1095
C7···Br2iii	3.583 (3)	H6···Br2xiii	3.5908
C7···C5v	3.493 (4)	H6···O3x	2.5500
C7···C6v	3.539 (4)	H6···C10x	3.5682
C8···O1iii	3.481 (3)	H6···H10xi	3.5884
C8···C1iii	3.577 (4)	H10···Br1vii	3.1969
C8···C4v	3.513 (4)	H10···Br1xiv	3.0191
C8···C9iii	3.558 (4)	H10···O3iii	2.9808
C9···O1iii	3.498 (3)	H10···C10iii	3.4959
C9···C4v	3.481 (4)	H10···H6xiv	3.5884
C9···C8v	3.558 (4)
C1—O1—C9	117.88 (17)	C3—C8—C4	119.99 (19)
O1—C1—C2	125.3 (3)	C3—C8—C9	120.3 (2)
C1—C2—C3	120.9 (2)	C4—C8—C9	119.73 (19)
C1—C2—C10	119.3 (3)	O1—C9—C7	117.29 (19)
C3—C2—C10	119.8 (2)	O1—C9—C8	122.01 (19)
O2—C3—C2	124.0 (2)	C7—C9—C8	120.7 (2)
O2—C3—C8	122.7 (3)	O3—C10—C2	123.0 (3)
C2—C3—C8	113.31 (19)	O1—C1—H1	117.367
C5—C4—C8	118.4 (2)	C2—C1—H1	117.366
Br1—C5—C4	119.25 (17)	C5—C4—H4	120.820
Br1—C5—C6	118.34 (16)	C8—C4—H4	120.803
C4—C5—C6	122.4 (2)	C5—C6—H6	120.481
C5—C6—C7	119.05 (19)	C7—C6—H6	120.472
Br2—C7—C6	120.49 (16)	O3—C10—H10	118.496
Br2—C7—C9	119.78 (17)	C2—C10—H10	118.482
C6—C7—C9	119.7 (2)
C1—O1—C9—C7	174.68 (18)	C8—C4—C5—Br1	−178.77 (18)
C1—O1—C9—C8	−4.8 (3)	C8—C4—C5—C6	0.9 (4)
C9—O1—C1—C2	3.1 (4)	H4—C4—C5—Br1	1.2
C9—O1—C1—H1	−176.9	H4—C4—C5—C6	−179.1
O1—C1—C2—C3	2.7 (4)	H4—C4—C8—C3	−2.2
O1—C1—C2—C10	−177.74 (19)	H4—C4—C8—C9	178.8
H1—C1—C2—C3	−177.3	Br1—C5—C6—C7	179.91 (14)
H1—C1—C2—C10	2.3	Br1—C5—C6—H6	−0.1
C1—C2—C3—O2	174.2 (3)	C4—C5—C6—C7	0.3 (4)
C1—C2—C3—C8	−6.2 (4)	C4—C5—C6—H6	−179.8
C1—C2—C10—O3	11.5 (4)	C5—C6—C7—Br2	179.31 (18)
C1—C2—C10—H10	−168.5	C5—C6—C7—C9	−1.1 (4)
C3—C2—C10—O3	−168.9 (3)	H6—C6—C7—Br2	−0.7
C3—C2—C10—H10	11.1	H6—C6—C7—C9	178.9
C10—C2—C3—O2	−5.4 (4)	Br2—C7—C9—O1	0.9 (3)
C10—C2—C3—C8	174.23 (19)	Br2—C7—C9—C8	−179.62 (14)
O2—C3—C8—C4	5.1 (4)	C6—C7—C9—O1	−178.7 (2)
O2—C3—C8—C9	−175.9 (2)	C6—C7—C9—C8	0.8 (4)
C2—C3—C8—C4	−174.51 (19)	C3—C8—C9—O1	0.8 (4)
C2—C3—C8—C9	4.5 (3)	C3—C8—C9—C7	−178.61 (19)
C5—C4—C8—C3	177.82 (19)	C4—C8—C9—O1	179.8 (2)
C5—C4—C8—C9	−1.2 (4)	C4—C8—C9—C7	0.4 (4)