4-Bromo-methyl-6-meth-oxy-2H-chromen-2-one.

The structure of the title coumarin derivative, C(11)H(9)BrO(3), is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the properties of coumarins, see: Kulkarni et al. (2006 ▶); Fylaktakidou et al. (2004 ▶); Neyts et al. (2009 ▶); Kempen et al. (2003 ▶). For structural analysis of coumarins, see: Gnanaguru et al. (1985 ▶); Munshi & Guru Row (2005 ▶); Gavuzzo et al. (1974 ▶); Moorthy et al. (2003 ▶); Katerinopoulos (2004 ▶). For Br-containing coumarins, see: Gaultier & Hauw (1965 ▶); Kokila et al. (1996 ▶); Vasudevan et al. (1991 ▶).

Experimental

Crystal data

C11H9BrO3

M = 269.09

Monoclinic,

a = 4.3573 (3) Å

b = 9.2859 (6) Å

c = 25.2677 (17) Å

β = 91.927 (3)°

V = 1021.79 (12) Å3

Z = 4

Mo Kα radiation

μ = 4.01 mm−1

T = 293 K

0.25 × 0.15 × 0.1 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.434, T max = 0.501

9950 measured reflections

2128 independent reflections

1501 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.101

S = 0.96

2128 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.93 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042005/bh2314sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042005/bh2314Isup2.hkl

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

C11H9BrO3	F(000) = 536
Mr = 269.09	Dx = 1.749 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3217 reflections
a = 4.3573 (3) Å	θ = 2.3–25.4°
b = 9.2859 (6) Å	µ = 4.01 mm−1
c = 25.2677 (17) Å	T = 293 K
β = 91.927 (3)°	Needle, colourless
V = 1021.79 (12) Å3	0.25 × 0.15 × 0.1 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2128 independent reflections
Radiation source: fine-focus sealed tube	1501 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω and φ scans	θmax = 26.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −5→3
Tmin = 0.434, Tmax = 0.501	k = −11→11
9950 measured reflections	l = −31→31

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0467P)2 + 1.203P] where P = (Fo2 + 2Fc2)/3
2128 reflections	(Δ/σ)max = 0.008
137 parameters	Δρmax = 0.93 e Å−3
0 restraints	Δρmin = −0.26 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.3658 (8)	0.2636 (4)	0.73840 (14)	0.0406 (9)
C2	0.4641 (8)	0.1339 (4)	0.71330 (13)	0.0375 (8)
H2	0.3944	0.0462	0.7260	0.045*
C3	0.6518 (7)	0.1332 (4)	0.67239 (13)	0.0321 (7)
C4	0.7577 (7)	0.2706 (4)	0.65171 (12)	0.0318 (7)
C5	0.9489 (7)	0.2851 (4)	0.60828 (13)	0.0348 (8)
H5	1.0139	0.2035	0.5905	0.042*
C6	1.0401 (7)	0.4188 (4)	0.59198 (13)	0.0378 (9)
C7	0.9456 (8)	0.5407 (4)	0.61872 (14)	0.0429 (9)
H7	1.0121	0.6311	0.6081	0.051*
C8	0.7556 (8)	0.5293 (4)	0.66048 (14)	0.0401 (9)
H8	0.6889	0.6113	0.6778	0.048*
C9	0.6642 (7)	0.3941 (4)	0.67652 (13)	0.0345 (8)
C10	0.7530 (9)	−0.0074 (4)	0.65024 (14)	0.0421 (9)
H10A	0.7086	−0.0837	0.6751	0.050*
H10B	0.9733	−0.0052	0.6460	0.050*
C11	1.2815 (9)	0.3270 (5)	0.51587 (15)	0.0535 (11)
H11A	1.4005	0.2554	0.5347	0.080*
H11B	1.3939	0.3612	0.4863	0.080*
H11C	1.0908	0.2856	0.5033	0.080*
O1	0.4744 (5)	0.3905 (3)	0.71899 (9)	0.0397 (6)
O2	0.1939 (7)	0.2719 (3)	0.77495 (11)	0.0569 (7)
O3	1.2213 (6)	0.4438 (3)	0.55030 (10)	0.0500 (7)
Br1	0.54925 (10)	−0.04981 (5)	0.582134 (17)	0.0612 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0437 (19)	0.039 (2)	0.039 (2)	−0.0003 (18)	0.0059 (16)	−0.0004 (17)
C2	0.0442 (19)	0.029 (2)	0.0390 (19)	−0.0025 (16)	0.0024 (16)	0.0004 (16)
C3	0.0345 (17)	0.027 (2)	0.0344 (18)	0.0024 (15)	0.0010 (14)	−0.0003 (14)
C4	0.0310 (16)	0.034 (2)	0.0301 (17)	0.0032 (15)	−0.0022 (13)	0.0012 (15)
C5	0.0338 (17)	0.036 (2)	0.0350 (18)	0.0037 (16)	0.0031 (14)	−0.0014 (16)
C6	0.0371 (18)	0.042 (2)	0.0343 (19)	−0.0030 (16)	0.0050 (15)	0.0044 (15)
C7	0.051 (2)	0.030 (2)	0.048 (2)	−0.0055 (18)	0.0027 (17)	0.0076 (17)
C8	0.050 (2)	0.029 (2)	0.042 (2)	0.0018 (17)	0.0008 (16)	−0.0045 (16)
C9	0.0335 (17)	0.037 (2)	0.0333 (18)	−0.0008 (15)	0.0020 (14)	−0.0007 (15)
C10	0.048 (2)	0.032 (2)	0.046 (2)	0.0050 (17)	0.0039 (17)	0.0013 (17)
C11	0.063 (3)	0.053 (3)	0.045 (2)	0.000 (2)	0.0162 (19)	0.002 (2)
O1	0.0483 (14)	0.0339 (15)	0.0376 (13)	0.0013 (12)	0.0117 (11)	−0.0024 (11)
O2	0.0759 (19)	0.0461 (18)	0.0508 (16)	0.0039 (15)	0.0305 (15)	−0.0005 (13)
O3	0.0618 (16)	0.0435 (17)	0.0460 (15)	−0.0072 (13)	0.0208 (13)	0.0030 (13)
Br1	0.0732 (3)	0.0518 (3)	0.0587 (3)	0.0043 (2)	0.0017 (2)	−0.0214 (2)

C1—O2	1.211 (4)	C7—C8	1.367 (5)
C1—O1	1.367 (4)	C7—H7	0.9300
C1—C2	1.434 (5)	C8—C9	1.382 (5)
C2—C3	1.340 (5)	C8—H8	0.9300
C2—H2	0.9300	C9—O1	1.377 (4)
C3—C4	1.459 (5)	C10—Br1	1.950 (4)
C3—C10	1.493 (5)	C10—H10A	0.9700
C4—C9	1.375 (5)	C10—H10B	0.9700
C4—C5	1.406 (5)	C11—O3	1.420 (5)
C5—C6	1.371 (5)	C11—H11A	0.9600
C5—H5	0.9300	C11—H11B	0.9600
C6—O3	1.357 (4)	C11—H11C	0.9600
C6—C7	1.388 (5)
O2—C1—O1	116.7 (3)	C7—C8—C9	119.0 (3)
O2—C1—C2	126.3 (4)	C7—C8—H8	120.5
O1—C1—C2	117.0 (3)	C9—C8—H8	120.5
C3—C2—C1	123.0 (3)	C4—C9—C8	122.1 (3)
C3—C2—H2	118.5	C4—C9—O1	122.0 (3)
C1—C2—H2	118.5	C8—C9—O1	115.9 (3)
C2—C3—C4	118.7 (3)	C3—C10—Br1	112.1 (2)
C2—C3—C10	119.3 (3)	C3—C10—H10A	109.2
C4—C3—C10	122.0 (3)	Br1—C10—H10A	109.2
C9—C4—C5	117.9 (3)	C3—C10—H10B	109.2
C9—C4—C3	117.6 (3)	Br1—C10—H10B	109.2
C5—C4—C3	124.5 (3)	H10A—C10—H10B	107.9
C6—C5—C4	120.4 (3)	O3—C11—H11A	109.5
C6—C5—H5	119.8	O3—C11—H11B	109.5
C4—C5—H5	119.8	H11A—C11—H11B	109.5
O3—C6—C5	124.7 (3)	O3—C11—H11C	109.5
O3—C6—C7	115.4 (3)	H11A—C11—H11C	109.5
C5—C6—C7	119.9 (3)	H11B—C11—H11C	109.5
C8—C7—C6	120.7 (3)	C1—O1—C9	121.6 (3)
C8—C7—H7	119.7	C6—O3—C11	118.0 (3)
C6—C7—H7	119.7
O2—C1—C2—C3	179.0 (3)	C5—C4—C9—C8	−0.9 (5)
O1—C1—C2—C3	−0.5 (5)	C3—C4—C9—C8	179.0 (3)
C1—C2—C3—C4	−1.0 (5)	C5—C4—C9—O1	179.3 (3)
C1—C2—C3—C10	177.4 (3)	C3—C4—C9—O1	−0.8 (4)
C2—C3—C4—C9	1.6 (4)	C7—C8—C9—C4	−0.2 (5)
C10—C3—C4—C9	−176.7 (3)	C7—C8—C9—O1	179.6 (3)
C2—C3—C4—C5	−178.5 (3)	C2—C3—C10—Br1	106.3 (3)
C10—C3—C4—C5	3.2 (5)	C4—C3—C10—Br1	−75.4 (3)
C9—C4—C5—C6	0.7 (5)	O2—C1—O1—C9	−178.1 (3)
C3—C4—C5—C6	−179.2 (3)	C2—C1—O1—C9	1.4 (5)
C4—C5—C6—O3	−179.3 (3)	C4—C9—O1—C1	−0.8 (5)
C4—C5—C6—C7	0.5 (5)	C8—C9—O1—C1	179.4 (3)
O3—C6—C7—C8	178.2 (3)	C5—C6—O3—C11	10.6 (5)
C5—C6—C7—C8	−1.6 (5)	C7—C6—O3—C11	−169.2 (3)
C6—C7—C8—C9	1.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.60	3.451 (4)	152
C2—H2···O2i	0.93	2.58	3.446 (5)	155
C10—H10A···O2i	0.97	2.57	3.437 (5)	148
C8—H8···O2ii	0.93	2.56	3.433 (5)	156
C10—H10A···O1iii	0.97	2.98	3.601 (4)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.60	3.451 (4)	152
C2—H2⋯O2i	0.93	2.58	3.446 (5)	155
C10—H10A⋯O2i	0.97	2.57	3.437 (5)	148
C8—H8⋯O2ii	0.93	2.56	3.433 (5)	156
C10—H10A⋯O1iii	0.97	2.98	3.601 (4)	122

Symmetry codes: (i) ; (ii) ; (iii) .