3-(2-Bromo-acet-yl)-6-fluoro-2H-chromen-2-one.

The non-H atoms of the title compound, C(11)H(6)BrFO(3), are essentially coplanar (r.m.s. deviation for all non-H atoms = 0.074 Å). In the crystal, the molecules are linked by C-H⋯O and C-H⋯Br inter-actions.

Related literature

For background to coumarins, see: Hooper et al.,(1982 ▶); Morris et al. (1971 ▶); Khalfan et al. (1987 ▶); Domagala et al. (1996 ▶); Eid et al. (1994 ▶).

Experimental

Crystal data

C11H6BrFO3

M = 285.06

Monoclinic,

a = 4.0590 (5) Å

b = 11.7719 (13) Å

c = 21.608 (2) Å

β = 94.318 (10)°

V = 1029.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 3.99 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.201, T max = 0.506

10491 measured reflections

2007 independent reflections

1438 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.065

S = 0.95

2007 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Window (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030960/bt5592sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030960/bt5592Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030960/bt5592Isup3.cml

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

C11H6BrFO3	F(000) = 560
Mr = 285.06	Dx = 1.839 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2007 reflections
a = 4.0590 (5) Å	θ = 3.3–26.0°
b = 11.7719 (13) Å	µ = 3.99 mm−1
c = 21.608 (2) Å	T = 293 K
β = 94.318 (10)°	Needle, yellow
V = 1029.6 (2) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2007 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1438 reflections with I > 2σ(I)
graphite	Rint = 0.036
Detector resolution: 16.0839 pixels mm-1	θmax = 26.0°, θmin = 3.3°
ω scans	h = −5→4
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.201, Tmax = 0.506	l = −26→26
10491 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0335P)2] where P = (Fo2 + 2Fc2)/3
2007 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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	0.29450 (7)	0.10699 (2)	−0.07092 (1)	0.0553 (1)
F1	0.1896 (5)	0.78595 (14)	0.21546 (8)	0.0728 (7)
O1	−0.1428 (4)	0.34429 (15)	0.16976 (8)	0.0450 (6)
O2	−0.1904 (5)	0.19171 (16)	0.11181 (9)	0.0630 (8)
O3	0.3915 (5)	0.34027 (16)	−0.01840 (9)	0.0606 (8)
C1	−0.0789 (7)	0.2860 (2)	0.11695 (12)	0.0405 (9)
C2	0.1133 (6)	0.3458 (2)	0.07253 (11)	0.0320 (8)
C3	0.1926 (6)	0.4562 (2)	0.08252 (11)	0.0351 (9)
C4	0.1121 (6)	0.5154 (2)	0.13648 (11)	0.0338 (8)
C5	0.1933 (7)	0.6296 (2)	0.14854 (13)	0.0428 (10)
C6	0.1139 (7)	0.6754 (2)	0.20335 (14)	0.0478 (10)
C7	−0.0399 (7)	0.6145 (3)	0.24778 (13)	0.0531 (11)
C8	−0.1208 (7)	0.5031 (3)	0.23639 (12)	0.0487 (10)
C9	−0.0485 (6)	0.4551 (2)	0.18082 (11)	0.0372 (9)
C10	0.2260 (6)	0.2882 (2)	0.01622 (12)	0.0362 (9)
C11	0.1383 (7)	0.1654 (2)	0.00482 (12)	0.0417 (9)
H3	0.30428	0.49474	0.05289	0.0421*
H5	0.29859	0.67285	0.11987	0.0514*
H7	−0.08758	0.64873	0.28485	0.0637*
H8	−0.22291	0.46050	0.26572	0.0585*
H11A	−0.10000	0.15723	0.00318	0.0500*
H11B	0.23180	0.12039	0.03940	0.0500*

	U11	U22	U33	U12	U13	U23
Br1	0.0651 (2)	0.0464 (2)	0.0556 (2)	−0.0025 (2)	0.0125 (2)	−0.0186 (2)
F1	0.1021 (14)	0.0435 (11)	0.0734 (12)	−0.0040 (10)	0.0097 (10)	−0.0273 (9)
O1	0.0634 (12)	0.0387 (11)	0.0351 (10)	−0.0073 (10)	0.0176 (9)	−0.0014 (9)
O2	0.0971 (16)	0.0386 (13)	0.0576 (13)	−0.0262 (12)	0.0342 (12)	−0.0060 (10)
O3	0.0977 (16)	0.0382 (11)	0.0506 (12)	−0.0227 (12)	0.0377 (12)	−0.0104 (10)
C1	0.0487 (17)	0.0389 (17)	0.0346 (15)	−0.0033 (14)	0.0086 (13)	0.0010 (13)
C2	0.0372 (15)	0.0297 (14)	0.0297 (14)	−0.0041 (12)	0.0070 (12)	0.0004 (11)
C3	0.0406 (15)	0.0320 (16)	0.0331 (15)	−0.0054 (12)	0.0065 (12)	0.0017 (11)
C4	0.0361 (14)	0.0329 (15)	0.0324 (14)	0.0025 (12)	0.0027 (12)	−0.0025 (12)
C5	0.0499 (17)	0.0359 (17)	0.0433 (16)	−0.0014 (13)	0.0075 (13)	−0.0040 (12)
C6	0.0550 (18)	0.0336 (17)	0.0540 (19)	0.0068 (15)	−0.0013 (16)	−0.0144 (14)
C7	0.063 (2)	0.055 (2)	0.0413 (17)	0.0138 (17)	0.0044 (15)	−0.0154 (15)
C8	0.0570 (19)	0.0529 (19)	0.0376 (16)	0.0047 (16)	0.0123 (14)	−0.0051 (14)
C9	0.0416 (16)	0.0338 (16)	0.0363 (15)	0.0039 (13)	0.0037 (13)	−0.0037 (12)
C10	0.0407 (15)	0.0321 (16)	0.0361 (15)	−0.0031 (12)	0.0053 (12)	−0.0013 (12)
C11	0.0477 (16)	0.0343 (16)	0.0446 (16)	−0.0053 (14)	0.0142 (13)	−0.0095 (12)

Br1—C11	1.926 (3)	C5—C6	1.362 (4)
F1—C6	1.358 (3)	C6—C7	1.384 (4)
O1—C1	1.373 (3)	C7—C8	1.370 (5)
O1—C9	1.375 (3)	C8—C9	1.379 (4)
O2—C1	1.201 (3)	C10—C11	1.505 (3)
O3—C10	1.209 (3)	C3—H3	0.9300
C1—C2	1.462 (4)	C5—H5	0.9300
C2—C3	1.352 (3)	C7—H7	0.9300
C2—C10	1.494 (3)	C8—H8	0.9300
C3—C4	1.418 (3)	C11—H11A	0.9700
C4—C5	1.404 (3)	C11—H11B	0.9700
C4—C9	1.393 (3)
Br1···O3	2.9861 (19)	C5···O3vi	3.404 (3)
Br1···C11i	3.747 (3)	C6···C7i	3.569 (4)
Br1···H11Ai	2.8900	C7···C6v	3.569 (4)
F1···O1ii	3.053 (3)	C8···C5v	3.574 (4)
F1···C8ii	3.226 (4)	C8···F1iv	3.226 (4)
F1···C9ii	3.259 (3)	C9···C4v	3.541 (3)
F1···H8iii	2.8400	C9···F1iv	3.259 (3)
O1···F1iv	3.053 (3)	C10···C1i	3.431 (4)
O2···C11	2.772 (3)	C10···O2i	3.230 (3)
O2···C2v	3.411 (3)	C11···Br1v	3.747 (3)
O2···C10v	3.230 (3)	C11···O2	2.772 (3)
O3···C2i	3.403 (3)	C1···H7vii	3.0600
O3···C3vi	3.296 (3)	C1···H11A	2.8800
O3···C5vi	3.404 (3)	C1···H11B	2.9200
O3···Br1	2.9861 (19)	C11···H11Ai	3.1000
O1···H7vii	2.7600	H3···O3	2.4300
O2···H7vii	2.5200	H3···H5	2.5500
O2···H11B	2.5500	H3···O3vi	2.4500
O2···H11A	2.4400	H5···H3	2.5500
O2···H11Bv	2.8500	H5···O3vi	2.6100
O3···H3	2.4300	H7···O1iii	2.7600
O3···H3vi	2.4500	H7···O2iii	2.5200
O3···H5vi	2.6100	H7···C1iii	3.0600
C1···C2v	3.420 (4)	H8···F1vii	2.8400
C1···C10v	3.431 (4)	H11A···Br1v	2.8900
C2···O2i	3.411 (3)	H11A···O2	2.4400
C2···O3v	3.403 (3)	H11A···C1	2.8800
C2···C1i	3.420 (4)	H11A···C11v	3.1000
C3···O3vi	3.296 (3)	H11B···O2	2.5500
C4···C9i	3.541 (3)	H11B···O2i	2.8500
C5···C8i	3.574 (4)	H11B···C1	2.9200
C1—O1—C9	123.43 (19)	C4—C9—C8	122.1 (2)
O1—C1—O2	116.5 (2)	O3—C10—C2	119.5 (2)
O1—C1—C2	116.7 (2)	O3—C10—C11	121.4 (2)
O2—C1—C2	126.9 (2)	C2—C10—C11	119.1 (2)
C1—C2—C3	119.4 (2)	Br1—C11—C10	113.15 (18)
C1—C2—C10	121.8 (2)	C2—C3—H3	119.00
C3—C2—C10	118.8 (2)	C4—C3—H3	119.00
C2—C3—C4	122.5 (2)	C4—C5—H5	121.00
C3—C4—C5	123.9 (2)	C6—C5—H5	121.00
C3—C4—C9	117.6 (2)	C6—C7—H7	120.00
C5—C4—C9	118.4 (2)	C8—C7—H7	120.00
C4—C5—C6	118.2 (2)	C7—C8—H8	120.00
F1—C6—C5	118.8 (2)	C9—C8—H8	121.00
F1—C6—C7	118.0 (3)	Br1—C11—H11A	109.00
C5—C6—C7	123.2 (2)	Br1—C11—H11B	109.00
C6—C7—C8	119.1 (3)	C10—C11—H11A	109.00
C7—C8—C9	119.0 (3)	C10—C11—H11B	109.00
O1—C9—C4	120.2 (2)	H11A—C11—H11B	108.00
O1—C9—C8	117.7 (2)
C9—O1—C1—O2	−176.2 (2)	C3—C4—C5—C6	−177.3 (3)
C9—O1—C1—C2	2.9 (3)	C9—C4—C5—C6	0.7 (4)
C1—O1—C9—C4	2.0 (3)	C3—C4—C9—O1	−4.2 (3)
C1—O1—C9—C8	−178.5 (2)	C3—C4—C9—C8	176.3 (2)
O1—C1—C2—C3	−5.6 (4)	C5—C4—C9—O1	177.7 (2)
O1—C1—C2—C10	174.2 (2)	C5—C4—C9—C8	−1.8 (4)
O2—C1—C2—C3	173.4 (3)	C4—C5—C6—F1	−179.7 (2)
O2—C1—C2—C10	−6.8 (4)	C4—C5—C6—C7	0.6 (4)
C1—C2—C3—C4	3.6 (4)	F1—C6—C7—C8	179.5 (3)
C10—C2—C3—C4	−176.3 (2)	C5—C6—C7—C8	−0.8 (4)
C1—C2—C10—O3	−178.2 (2)	C6—C7—C8—C9	−0.4 (4)
C1—C2—C10—C11	0.2 (4)	C7—C8—C9—O1	−177.8 (2)
C3—C2—C10—O3	1.7 (4)	C7—C8—C9—C4	1.7 (4)
C3—C2—C10—C11	−179.9 (2)	O3—C10—C11—Br1	−3.2 (3)
C2—C3—C4—C5	179.4 (3)	C2—C10—C11—Br1	178.48 (18)
C2—C3—C4—C9	1.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3vi	0.93	2.45	3.296 (3)	152
C7—H7···O2iii	0.93	2.52	3.425 (3)	164
C11—H11A···Br1v	0.97	2.89	3.747 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.93	2.45	3.296 (3)	152
C7—H7⋯O2ii	0.93	2.52	3.425 (3)	164
C11—H11A⋯Br1iii	0.97	2.89	3.747 (3)	148

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