5-Fluoro-1,3-dihydro-2,1-benzoxaborol-1-ol.

In the crystal structure of the title compound, C(7)H(6)BFO(2), a broad-spectrum anti-fungal drug (AN2690), the planar [maximum deviation 0.035 (1) Å] mol-ecules form centrosymmetric R(2) (2)(8) dimers via strong O-H⋯O hydrogen bonds. The dimers are arranged into layers by weak inter-molecular C-H⋯O and C-H⋯F hydrogen bonds. The symmetry of this two-dimensional supra-molecular assembly can be described by the layer group p and topologically classified as a simple uninodal four-connected two-dimensional network of a (4.4.4.4.6.6) topology. Further weak C-H⋯O inter-actions build up the three-dimensional structure.

Related literature

For the review of the synthesis, properties and applications of benzoxaboroles, see: Adamczyk-Woźniak et al. (2009 ▶). For the biological activity of the title compound, see: Baker et al. (2005 ▶, 2006 ▶); Hui et al. (2007 ▶); Rock et al. (2007 ▶). For the synthesis see: Baker et al. (2006 ▶), Gunasekera et al. (2007 ▶). For related structures, see: Adamczyk-Woźniak et al. (2010 ▶); Tan et al. (2001 ▶); Yamamoto et al. (2005 ▶); Zhdankin et al. (1999 ▶). For hydrogen-bond graph-set descriptors and layer symmetry groups, see: Etter (1990 ▶) and Inter­national Tables for Crystallography (2006 ▶), respectively.

Experimental

Crystal data

C7H6BFO2

M = 151.93

Triclinic,

a = 3.8799 (3) Å

b = 6.3077 (5) Å

c = 14.0735 (12) Å

α = 98.068 (7)°

β = 91.564 (7)°

γ = 100.473 (7)°

V = 334.84 (5) Å3

Z = 2

Cu Kα radiation

μ = 1.06 mm−1

T = 100 K

0.60 × 0.35 × 0.20 mm

Data collection

Oxford Diffraction Gemini A Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.731, T max = 1.000

3451 measured reflections

1193 independent reflections

1147 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.088

S = 1.07

1193 reflections

105 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks . DOI: 10.1107/S1600536811001632/fj2381sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001632/fj2381Isup2.hkl

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

C7H6BFO2	Z = 2
Mr = 151.93	F(000) = 156
Triclinic, P1	Dx = 1.507 Mg m−3
Hall symbol: -P 1	Melting point: 408 K
a = 3.8799 (3) Å	Cu Kα radiation, λ = 1.5418 Å
b = 6.3077 (5) Å	Cell parameters from 3116 reflections
c = 14.0735 (12) Å	θ = 3.2–67.1°
α = 98.068 (7)°	µ = 1.06 mm−1
β = 91.564 (7)°	T = 100 K
γ = 100.473 (7)°	Prism, light yellow
V = 334.84 (5) Å3	0.60 × 0.35 × 0.20 mm

Oxford Diffraction Gemini A Ultra diffractometer	1193 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1147 reflections with I > 2σ(I)
mirror	Rint = 0.016
Detector resolution: 10.3347 pixels mm-1	θmax = 67.1°, θmin = 3.2°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −7→7
Tmin = 0.731, Tmax = 1.000	l = −16→14
3451 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0511P)2 + 0.1152P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1193 reflections	Δρmax = 0.33 e Å−3
105 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.046 (5)

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. (Oxford Diffraction, 2006)

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.

	x	y	z	Uiso*/Ueq
O2	0.9636 (2)	1.22613 (14)	0.60638 (7)	0.0189 (3)
F1	0.0385 (2)	0.70856 (13)	0.93059 (5)	0.0282 (3)
O1	0.7364 (2)	0.84381 (13)	0.56821 (6)	0.0171 (3)
C3	0.2566 (3)	0.6725 (2)	0.77652 (9)	0.0185 (3)
H3	0.1624	0.5207	0.7660	0.022*
C4	0.2168 (3)	0.8036 (2)	0.86129 (9)	0.0200 (3)
C2	0.4422 (3)	0.7757 (2)	0.70750 (9)	0.0162 (3)
C1	0.5825 (3)	0.9983 (2)	0.72234 (9)	0.0167 (3)
C5	0.3485 (3)	1.0251 (2)	0.87950 (9)	0.0207 (3)
H5	0.3121	1.1083	0.9388	0.025*
C6	0.5346 (3)	1.1237 (2)	0.80968 (9)	0.0186 (3)
H6	0.6291	1.2754	0.8210	0.022*
B1	0.7783 (3)	1.0404 (2)	0.63011 (10)	0.0164 (3)
C7	0.5248 (3)	0.6711 (2)	0.61026 (9)	0.0170 (3)
H7B	0.6562	0.5526	0.6164	0.020*
H7A	0.3064	0.6096	0.5701	0.020*
H2	1.061 (5)	1.212 (3)	0.5545 (15)	0.040 (5)*

	U11	U22	U33	U12	U13	U23
O2	0.0245 (5)	0.0147 (5)	0.0169 (5)	0.0025 (4)	0.0053 (4)	0.0011 (3)
F1	0.0329 (5)	0.0323 (5)	0.0196 (4)	0.0035 (4)	0.0106 (3)	0.0065 (3)
O1	0.0208 (5)	0.0145 (5)	0.0154 (5)	0.0019 (3)	0.0046 (3)	0.0017 (3)
C3	0.0178 (6)	0.0188 (6)	0.0193 (7)	0.0037 (5)	0.0009 (5)	0.0033 (5)
C4	0.0181 (6)	0.0273 (7)	0.0160 (6)	0.0052 (5)	0.0038 (5)	0.0061 (5)
C2	0.0149 (6)	0.0174 (6)	0.0168 (6)	0.0055 (5)	−0.0004 (4)	0.0014 (5)
C1	0.0154 (6)	0.0174 (6)	0.0178 (7)	0.0051 (5)	−0.0011 (5)	0.0021 (5)
C5	0.0212 (6)	0.0256 (7)	0.0155 (6)	0.0083 (5)	0.0008 (5)	−0.0016 (5)
C6	0.0187 (6)	0.0179 (6)	0.0188 (6)	0.0049 (5)	−0.0001 (5)	−0.0007 (5)
B1	0.0162 (6)	0.0162 (7)	0.0172 (7)	0.0055 (5)	−0.0011 (5)	0.0009 (5)
C7	0.0197 (6)	0.0135 (6)	0.0174 (6)	0.0017 (5)	0.0036 (5)	0.0021 (5)

O2—B1	1.3483 (18)	C2—C1	1.3948 (18)
O2—H2	0.83 (2)	C2—C7	1.5025 (17)
F1—C4	1.3562 (15)	C1—C6	1.4013 (17)
O1—B1	1.3922 (17)	C1—B1	1.5522 (18)
O1—C7	1.4471 (15)	C5—H5	0.9500
C3—H3	0.9500	C5—C6	1.3856 (18)
C3—C4	1.3822 (19)	C6—H6	0.9500
C3—C2	1.3897 (18)	C7—H7B	0.9900
C4—C5	1.3829 (19)	C7—H7A	0.9900
O2—B1—O1	121.51 (12)	C2—C3—H3	121.9
O2—B1—C1	130.25 (12)	C2—C1—C6	119.16 (12)
F1—C4—C3	117.85 (12)	C2—C1—B1	104.93 (11)
F1—C4—C5	118.27 (12)	C2—C7—H7B	110.7
O1—B1—C1	108.24 (11)	C2—C7—H7A	110.7
O1—C7—C2	105.45 (9)	C1—C2—C7	110.88 (11)
O1—C7—H7B	110.7	C1—C6—H6	120.2
O1—C7—H7A	110.7	C5—C6—C1	119.66 (12)
C3—C4—C5	123.88 (12)	C5—C6—H6	120.2
C3—C2—C1	122.36 (12)	C6—C1—B1	135.86 (12)
C3—C2—C7	126.75 (11)	C6—C5—H5	120.6
C4—C3—H3	121.9	B1—O2—H2	115.3 (13)
C4—C3—C2	116.12 (12)	B1—O1—C7	110.46 (10)
C4—C5—H5	120.6	H7B—C7—H7A	108.8
C4—C5—C6	118.82 (12)
F1—C4—C5—C6	179.28 (10)	C2—C1—B1—O2	−179.25 (12)
C3—C4—C5—C6	−0.58 (19)	C2—C1—B1—O1	0.71 (13)
C3—C2—C1—C6	−0.23 (17)	C1—C2—C7—O1	2.08 (13)
C3—C2—C1—B1	177.60 (11)	C6—C1—B1—O2	−2.0 (2)
C3—C2—C7—O1	−177.19 (11)	C6—C1—B1—O1	178.00 (12)
C4—C3—C2—C1	0.24 (18)	B1—O1—C7—C2	−1.57 (13)
C4—C3—C2—C7	179.42 (11)	B1—C1—C6—C5	−177.18 (12)
C4—C5—C6—C1	0.57 (18)	C7—O1—B1—O2	−179.45 (10)
C2—C3—C4—F1	−179.69 (9)	C7—O1—B1—C1	0.59 (13)
C2—C3—C4—C5	0.17 (19)	C7—C2—C1—C6	−179.53 (10)
C2—C1—C6—C5	−0.19 (17)	C7—C2—C1—B1	−1.70 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.83 (2)	1.93 (2)	2.7614 (13)	175 (2)
C7—H7B···O2ii	0.99	2.55	3.5325 (15)	172
C5—H5···F1iii	0.95	2.58	3.4779 (14)	157
C7—H7A···O2iv	0.99	2.66	3.2172 (14)	116
C3—H3···O2iv	0.95	2.70	3.4276 (14)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.83 (2)	1.93 (2)	2.7614 (13)	175 (2)
C7—H7B⋯O2ii	0.99	2.55	3.5325 (15)	172
C5—H5⋯F1iii	0.95	2.58	3.4779 (14)	157
C7—H7A⋯O2iv	0.99	2.66	3.2172 (14)	116
C3—H3⋯O2iv	0.95	2.70	3.4276 (14)	134

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