2-Hy-droxy-2-trifluoro-methyl-3,4-dihydro-2H-1-benzopyran-4-one.

The heterocyclic ring in the title compound, C(10)H(7)F(3)O(3), has a half-boat conformation with the hy-droxy-bearing C atom lying 0.595 (3) Å out of the plane of the five remaining atoms (r.m.s. deviation = 0.022 Å) in the direction of the hy-droxy O atom. Linear supra-molecular chains along the a axis, sustained by O-H⋯O hydrogen bonds between the hy-droxy H and ketone O atoms, feature in the crystal packing. These chains are connected into a three-dimensional architecture by C-H⋯O and C-H⋯F contacts.

Related literature

For an example of an anti­cipated product formed between the reaction of bis­(ethyl­idene)ethane-1,2-diamine with an anhydride, see: Asiri et al. (2011 ▶). For the crystal structure of a related compound, see: Wang et al. (1999 ▶).

Experimental

Crystal data

C10H7F3O3

M = 232.16

Triclinic,

a = 5.9516 (5) Å

b = 8.5188 (7) Å

c = 10.2036 (8) Å

α = 66.985 (8)°

β = 80.380 (7)°

γ = 78.311 (7)°

V = 464.05 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 100 K

0.30 × 0.30 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.528, T max = 1.000

3161 measured reflections

2126 independent reflections

1665 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.171

S = 1.06

2126 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029170/su2468sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029170/su2468Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029170/su2468Isup3.cml

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

C10H7F3O3	Z = 2
Mr = 232.16	F(000) = 236
Triclinic, P1	Dx = 1.661 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9516 (5) Å	Cell parameters from 1358 reflections
b = 8.5188 (7) Å	θ = 2.6–27.5°
c = 10.2036 (8) Å	µ = 0.16 mm−1
α = 66.985 (8)°	T = 100 K
β = 80.380 (7)°	Block, colourless
γ = 78.311 (7)°	0.30 × 0.30 × 0.15 mm
V = 464.05 (7) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	2126 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1665 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.6°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −8→11
Tmin = 0.528, Tmax = 1.000	l = −12→13
3161 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2126 reflections	(Δ/σ)max = 0.001
149 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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
F1	1.0703 (2)	0.18377 (19)	0.58363 (13)	0.0304 (4)
F2	0.8148 (2)	0.01895 (17)	0.63198 (13)	0.0313 (4)
F3	0.7818 (2)	0.26448 (18)	0.45820 (12)	0.0319 (4)
O1	0.7796 (2)	0.16833 (18)	0.82675 (13)	0.0178 (3)
O2	0.1156 (2)	0.4181 (2)	0.79358 (15)	0.0235 (4)
O3	0.7560 (3)	0.43915 (19)	0.64399 (14)	0.0209 (4)
C1	0.6584 (3)	0.2102 (3)	0.93909 (19)	0.0175 (4)
C2	0.7742 (4)	0.1650 (3)	1.0596 (2)	0.0211 (5)
H2	0.9293	0.1085	1.0621	0.025*
C3	0.6602 (4)	0.2034 (3)	1.1755 (2)	0.0232 (5)
H3	0.7378	0.1719	1.2583	0.028*
C4	0.4331 (4)	0.2877 (3)	1.1729 (2)	0.0237 (5)
H4	0.3574	0.3141	1.2531	0.028*
C5	0.3191 (3)	0.3325 (3)	1.0531 (2)	0.0213 (5)
H5	0.1641	0.3892	1.0514	0.026*
C6	0.4307 (3)	0.2950 (3)	0.93380 (19)	0.0175 (4)
C7	0.3132 (3)	0.3418 (3)	0.8052 (2)	0.0188 (4)
C8	0.4479 (3)	0.2822 (3)	0.6894 (2)	0.0195 (4)
H8A	0.4129	0.1672	0.7043	0.023*
H8B	0.3997	0.3636	0.5950	0.023*
C9	0.7043 (3)	0.2716 (3)	0.68994 (19)	0.0186 (4)
C10	0.8435 (3)	0.1831 (3)	0.59025 (19)	0.0202 (5)
H3o	0.893 (6)	0.430 (5)	0.666 (3)	0.064 (10)*

	U11	U22	U33	U12	U13	U23
F1	0.0218 (7)	0.0439 (9)	0.0346 (7)	−0.0066 (6)	0.0015 (5)	−0.0251 (7)
F2	0.0428 (9)	0.0221 (7)	0.0318 (7)	−0.0061 (6)	0.0050 (6)	−0.0156 (6)
F3	0.0443 (9)	0.0362 (8)	0.0169 (6)	0.0016 (6)	−0.0076 (5)	−0.0135 (6)
O1	0.0193 (7)	0.0196 (8)	0.0144 (6)	0.0026 (6)	−0.0048 (5)	−0.0075 (6)
O2	0.0167 (7)	0.0255 (8)	0.0282 (8)	−0.0012 (6)	−0.0067 (6)	−0.0091 (7)
O3	0.0206 (8)	0.0202 (8)	0.0234 (7)	−0.0026 (6)	−0.0062 (6)	−0.0083 (6)
C1	0.0222 (10)	0.0153 (10)	0.0148 (9)	−0.0017 (8)	−0.0037 (8)	−0.0054 (8)
C2	0.0236 (11)	0.0194 (11)	0.0204 (9)	0.0016 (8)	−0.0070 (8)	−0.0079 (8)
C3	0.0335 (12)	0.0200 (11)	0.0159 (9)	−0.0024 (9)	−0.0064 (8)	−0.0057 (8)
C4	0.0314 (12)	0.0222 (11)	0.0180 (9)	−0.0064 (9)	0.0035 (8)	−0.0094 (9)
C5	0.0189 (10)	0.0193 (11)	0.0256 (10)	−0.0029 (8)	−0.0018 (8)	−0.0085 (9)
C6	0.0182 (10)	0.0172 (10)	0.0169 (9)	−0.0043 (8)	−0.0008 (7)	−0.0057 (8)
C7	0.0161 (10)	0.0187 (10)	0.0221 (9)	−0.0067 (8)	−0.0033 (8)	−0.0055 (8)
C8	0.0181 (10)	0.0224 (11)	0.0195 (9)	−0.0040 (8)	−0.0055 (8)	−0.0073 (8)
C9	0.0218 (10)	0.0198 (10)	0.0156 (9)	0.0005 (8)	−0.0067 (8)	−0.0080 (8)
C10	0.0234 (11)	0.0224 (11)	0.0177 (9)	−0.0044 (8)	−0.0037 (8)	−0.0092 (8)

F1—C10	1.341 (2)	C3—C4	1.395 (3)
F2—C10	1.332 (2)	C3—H3	0.9500
F3—C10	1.328 (2)	C4—C5	1.381 (3)
O1—C1	1.379 (2)	C4—H4	0.9500
O1—C9	1.419 (2)	C5—C6	1.405 (3)
O2—C7	1.223 (3)	C5—H5	0.9500
O3—C9	1.400 (2)	C6—C7	1.467 (3)
O3—H3o	0.86 (3)	C7—C8	1.512 (3)
C1—C2	1.393 (2)	C8—C9	1.511 (3)
C1—C6	1.400 (3)	C8—H8A	0.9900
C2—C3	1.382 (3)	C8—H8B	0.9900
C2—H2	0.9500	C9—C10	1.534 (3)
C1—O1—C9	115.51 (14)	O2—C7—C8	121.50 (17)
C9—O3—H3o	107 (2)	C6—C7—C8	115.72 (17)
O1—C1—C2	116.74 (17)	C9—C8—C7	111.33 (15)
O1—C1—C6	122.38 (16)	C9—C8—H8A	109.4
C2—C1—C6	120.89 (17)	C7—C8—H8A	109.4
C3—C2—C1	119.07 (19)	C9—C8—H8B	109.4
C3—C2—H2	120.5	C7—C8—H8B	109.4
C1—C2—H2	120.5	H8A—C8—H8B	108.0
C2—C3—C4	121.14 (18)	O3—C9—O1	111.26 (14)
C2—C3—H3	119.4	O3—C9—C8	108.60 (17)
C4—C3—H3	119.4	O1—C9—C8	111.81 (16)
C5—C4—C3	119.62 (18)	O3—C9—C10	108.97 (16)
C5—C4—H4	120.2	O1—C9—C10	104.54 (16)
C3—C4—H4	120.2	C8—C9—C10	111.61 (15)
C4—C5—C6	120.47 (19)	F3—C10—F2	107.65 (15)
C4—C5—H5	119.8	F3—C10—F1	107.39 (16)
C6—C5—H5	119.8	F2—C10—F1	106.72 (17)
C1—C6—C5	118.81 (17)	F3—C10—C9	110.52 (17)
C1—C6—C7	119.75 (17)	F2—C10—C9	112.73 (16)
C5—C6—C7	121.44 (18)	F1—C10—C9	111.56 (15)
O2—C7—C6	122.72 (18)
C9—O1—C1—C2	−154.98 (17)	O2—C7—C8—C9	152.82 (19)
C9—O1—C1—C6	24.6 (2)	C6—C7—C8—C9	−30.0 (2)
O1—C1—C2—C3	−179.77 (17)	C1—O1—C9—O3	70.0 (2)
C6—C1—C2—C3	0.7 (3)	C1—O1—C9—C8	−51.6 (2)
C1—C2—C3—C4	−0.6 (3)	C1—O1—C9—C10	−172.49 (15)
C2—C3—C4—C5	0.5 (3)	C7—C8—C9—O3	−69.3 (2)
C3—C4—C5—C6	−0.5 (3)	C7—C8—C9—O1	53.8 (2)
O1—C1—C6—C5	179.84 (16)	C7—C8—C9—C10	170.52 (16)
C2—C1—C6—C5	−0.6 (3)	O3—C9—C10—F3	−63.4 (2)
O1—C1—C6—C7	0.2 (3)	O1—C9—C10—F3	177.59 (14)
C2—C1—C6—C7	179.72 (17)	C8—C9—C10—F3	56.6 (2)
C4—C5—C6—C1	0.5 (3)	O3—C9—C10—F2	176.10 (15)
C4—C5—C6—C7	−179.83 (18)	O1—C9—C10—F2	57.1 (2)
C1—C6—C7—O2	−178.94 (18)	C8—C9—C10—F2	−64.0 (2)
C5—C6—C7—O2	1.4 (3)	O3—C9—C10—F1	56.0 (2)
C1—C6—C7—C8	3.9 (3)	O1—C9—C10—F1	−63.0 (2)
C5—C6—C7—C8	−175.77 (17)	C8—C9—C10—F1	175.96 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2i	0.86 (3)	1.97 (3)	2.768 (2)	154 (3)
C2—H2···O1ii	0.95	2.60	3.444 (3)	148
C3—H3···F3iii	0.95	2.52	3.338 (3)	144
C8—H8A···F1iv	0.99	2.51	3.033 (2)	113
C8—H8B···O3v	0.99	2.56	3.547 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O2i	0.86 (3)	1.97 (3)	2.768 (2)	154 (3)
C2—H2⋯O1ii	0.95	2.60	3.444 (3)	148
C3—H3⋯F3iii	0.95	2.52	3.338 (3)	144
C8—H8A⋯F1iv	0.99	2.51	3.033 (2)	113
C8—H8B⋯O3v	0.99	2.56	3.547 (2)	175

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