3-Bromo-chroman-4-one.

The heterocyclic ring of the title compound, C9H7BrO2, obtained by bromination of 4-chromanone with copper bromide, adopts a half-chair conformation. The supramol-ecular structure is governed by a weak C-H⋯O hydrogen bond. There is also π-π stacking between symmetry-related benzene rings; the centroid-centroid distance is 3.9464 (18), the perpendicular distance between the rings is 3.4703 (11) and the offset is 1.879 Å.

Related literature

For similar structures, see: Schollmeyer et al. (2005 ▶); Piel et al. (2011 ▶); Betz et al. (2011 ▶). For synthesis involving chromanone inter­mediates, see: Simas et al. (2002 ▶); Zhang et al. (2008 ▶). For the biological activity of chromanone derivatives, see: Cho et al. (1996 ▶); Xu et al. (1998 ▶); Shaikh et al. (2012 ▶, 2013a ▶,b ▶).

Experimental

Crystal data

C9H7BrO2

M = 227.06

Monoclinic,

a = 10.0846 (7) Å

b = 7.9104 (6) Å

c = 10.9330 (8) Å

β = 110.164 (2)°

V = 818.71 (10) Å3

Z = 4

Mo Kα radiation

μ = 4.97 mm−1

T = 173 K

0.16 × 0.12 × 0.12 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.504, T max = 0.587

5434 measured reflections

1659 independent reflections

1392 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.061

S = 1.05

1659 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005394/go2082sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005394/go2082Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005394/go2082Isup3.cml

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

C9H7BrO2	F(000) = 448
Mr = 227.06	Dx = 1.842 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 5434 reflections
a = 10.0846 (7) Å	θ = 2.2–26.4°
b = 7.9104 (6) Å	µ = 4.97 mm−1
c = 10.9330 (8) Å	T = 173 K
β = 110.164 (2)°	Block, colourless
V = 818.71 (10) Å3	0.16 × 0.12 × 0.12 mm
Z = 4

Bruker Kappa DUO APEXII diffractometer	1659 independent reflections
Radiation source: fine-focus sealed tube	1392 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
0.5° φ scans and ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −12→8
Tmin = 0.504, Tmax = 0.587	k = −9→9
5434 measured reflections	l = −7→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0298P)2 + 0.3551P] where P = (Fo2 + 2Fc2)/3
1659 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. 1H NMR (400 MHz, CDCl3): δ (p.p.m.): 4.53–4.65 (3H, m, H-2a, H-2b & H-3), 6.98–7.06 (2H, m, H-6 & H-8), 7.48–7.52 (1H, m, H-7), 7.89 (1H, dd, J = 1.60, 7.92 Hz, H-5). 13C NMR (400 MHz, CDCl3): δ (p.p.m.): 45.43 (C-3), 71.26 (C-2), 117.95 (C-8), 118.77 (C-10), 122.33 (C-6), 128.24 (C-7), 136.74 (C-5), 160.65 (C-9), 185.21 (C-4).

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
Br1	0.22559 (3)	0.04339 (3)	0.04673 (3)	0.03040 (11)
O1	0.33588 (18)	0.3999 (2)	0.20473 (16)	0.0258 (4)
O2	0.00306 (19)	0.3386 (2)	−0.13799 (18)	0.0348 (5)
C2	0.2062 (3)	0.3261 (3)	0.2053 (2)	0.0261 (6)
H2A	0.1470	0.4155	0.2238	0.031*
H2B	0.2276	0.2418	0.2764	0.031*
C3	0.1239 (3)	0.2415 (3)	0.0786 (2)	0.0251 (6)
H3	0.0297	0.2053	0.0807	0.030*
C4	0.1031 (3)	0.3566 (3)	−0.0374 (2)	0.0242 (5)
C5	0.2106 (3)	0.5942 (3)	−0.1218 (3)	0.0274 (6)
H5	0.1348	0.5872	−0.2026	0.033*
C6	0.3170 (3)	0.7098 (3)	−0.1066 (3)	0.0330 (7)
H6	0.3148	0.7825	−0.1764	0.040*
C7	0.4279 (3)	0.7196 (3)	0.0121 (3)	0.0339 (7)
H7	0.5018	0.7987	0.0223	0.041*
C8	0.4323 (3)	0.6165 (3)	0.1148 (3)	0.0284 (6)
H8	0.5080	0.6253	0.1955	0.034*
C9	0.3249 (3)	0.4994 (3)	0.0995 (2)	0.0212 (5)
C10	0.2132 (3)	0.4865 (3)	−0.0193 (2)	0.0210 (5)

	U11	U22	U33	U12	U13	U23
Br1	0.04127 (18)	0.01971 (15)	0.03327 (17)	0.00253 (11)	0.01674 (13)	0.00006 (12)
O1	0.0294 (10)	0.0252 (9)	0.0199 (9)	−0.0012 (8)	0.0046 (8)	0.0022 (8)
O2	0.0315 (11)	0.0358 (11)	0.0289 (11)	0.0004 (8)	−0.0002 (9)	−0.0033 (9)
C2	0.0339 (15)	0.0240 (13)	0.0218 (13)	0.0027 (11)	0.0116 (12)	0.0023 (11)
C3	0.0265 (13)	0.0225 (13)	0.0294 (14)	0.0016 (11)	0.0137 (12)	−0.0006 (11)
C4	0.0259 (13)	0.0233 (13)	0.0242 (13)	0.0058 (11)	0.0095 (12)	−0.0027 (11)
C5	0.0392 (15)	0.0233 (13)	0.0217 (13)	0.0094 (12)	0.0129 (12)	0.0008 (11)
C6	0.0521 (18)	0.0196 (13)	0.0364 (16)	0.0075 (12)	0.0269 (15)	0.0071 (12)
C7	0.0394 (16)	0.0199 (14)	0.0504 (18)	−0.0021 (12)	0.0255 (15)	−0.0019 (13)
C8	0.0276 (14)	0.0236 (13)	0.0348 (15)	−0.0006 (11)	0.0116 (12)	−0.0066 (12)
C9	0.0263 (13)	0.0175 (12)	0.0209 (12)	0.0033 (9)	0.0097 (11)	−0.0014 (9)
C10	0.0267 (13)	0.0172 (12)	0.0221 (13)	0.0032 (10)	0.0122 (11)	−0.0027 (10)

Br1—C3	1.969 (2)	C5—C6	1.375 (4)
O1—C9	1.367 (3)	C5—C10	1.401 (4)
O1—C2	1.434 (3)	C5—H5	0.9500
O2—C4	1.218 (3)	C6—C7	1.393 (4)
C2—C3	1.505 (3)	C6—H6	0.9500
C2—H2A	0.9900	C7—C8	1.376 (4)
C2—H2B	0.9900	C7—H7	0.9500
C3—C4	1.515 (3)	C8—C9	1.390 (4)
C3—H3	1.0000	C8—H8	0.9500
C4—C10	1.476 (4)	C9—C10	1.399 (4)
C9—O1—C2	115.40 (19)	C6—C5—H5	119.7
O1—C2—C3	113.01 (19)	C10—C5—H5	119.7
O1—C2—H2A	109.0	C5—C6—C7	119.5 (2)
C3—C2—H2A	109.0	C5—C6—H6	120.2
O1—C2—H2B	109.0	C7—C6—H6	120.2
C3—C2—H2B	109.0	C8—C7—C6	121.1 (3)
H2A—C2—H2B	107.8	C8—C7—H7	119.5
C2—C3—C4	112.1 (2)	C6—C7—H7	119.5
C2—C3—Br1	111.18 (17)	C7—C8—C9	119.5 (3)
C4—C3—Br1	105.11 (15)	C7—C8—H8	120.3
C2—C3—H3	109.4	C9—C8—H8	120.3
C4—C3—H3	109.4	O1—C9—C8	116.7 (2)
Br1—C3—H3	109.4	O1—C9—C10	123.0 (2)
O2—C4—C10	123.6 (2)	C8—C9—C10	120.3 (2)
O2—C4—C3	121.3 (2)	C9—C10—C5	119.0 (2)
C10—C4—C3	115.2 (2)	C9—C10—C4	120.2 (2)
C6—C5—C10	120.6 (3)	C5—C10—C4	120.7 (2)
C9—O1—C2—C3	49.0 (3)	C7—C8—C9—O1	179.5 (2)
O1—C2—C3—C4	−51.4 (3)	C7—C8—C9—C10	−0.1 (4)
O1—C2—C3—Br1	66.0 (2)	O1—C9—C10—C5	179.9 (2)
C2—C3—C4—O2	−153.8 (2)	C8—C9—C10—C5	−0.5 (3)
Br1—C3—C4—O2	85.3 (2)	O1—C9—C10—C4	−2.5 (3)
C2—C3—C4—C10	27.4 (3)	C8—C9—C10—C4	177.1 (2)
Br1—C3—C4—C10	−93.5 (2)	C6—C5—C10—C9	0.6 (3)
C10—C5—C6—C7	0.0 (4)	C6—C5—C10—C4	−177.0 (2)
C5—C6—C7—C8	−0.6 (4)	O2—C4—C10—C9	179.9 (2)
C6—C7—C8—C9	0.7 (4)	C3—C4—C10—C9	−1.4 (3)
C2—O1—C9—C8	158.5 (2)	O2—C4—C10—C5	−2.5 (4)
C2—O1—C9—C10	−21.8 (3)	C3—C4—C10—C5	176.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.99	2.44	3.311 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.99	2.44	3.311 (3)	146

Symmetry code: (i) .