1-(4-Fluoro­phen­yl)-2-(1H-imidazol-1-yl)ethanol

Liu, D.; Li, C.; Tian, X.; Li, S.; Xiao, T.

doi:10.1107/S1600536811053505

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o152

doi:10.1107/S1600536811053505

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1-(4-Fluorophenyl)-2-(1H-imidazol-1-yl)ethanol

Dong-liang Liu,^a Chen Li,^a Xin Tian,^a Song Li ^a and Tao Xiao ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: taoxiao@njut.edu.cn

(Received 13 November 2011; accepted 12 December 2011; online 17 December 2011)

In the title compound, C₁₁H₁₁FN₂O, the dihedral angle between the mean planes of the two rings is 1.30 (4)°. In the crystal, O—H⋯N hydrogen bonds link the molecules into chains along the b axis.

Related literature

For related compounds containing a 2-(1H-imidazol-1-yl)-1-phenylethanol fragment, see: Porretta et al. (1993 ). For related structures, see: Tao et al. (2007 ); Liu et al. (2011 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₁FN₂O
M_r = 206.22
Monoclinic, P 2₁
a = 7.1220 (14) Å
b = 5.4690 (11) Å
c = 12.981 (3) Å
β = 98.13 (3)°
V = 500.53 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: multi-scan (North et al., 1968 ) T_min = 0.970, T_max = 0.990
1992 measured reflections
1024 independent reflections
876 reflections with I > 2σ(I)
R_int = 0.029
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.124
S = 1.00
1024 reflections
139 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H0A⋯N2ⁱ	0.87 (4)	1.90 (4)	2.762 (4)	171 (5)
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811053505/zq2137sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053505/zq2137Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053505/zq2137Isup3.cml

checkCIF report

Comment top

The title compound, C₁₁H₁₁ON₂F, is the key intermediate in the synthesis of a new kind of antifungal drug (Porretta et al., 1993). As a part of our ongoing studies (Tao et al., 2007; Liu et al., 2011), the crystal structure determination of the title compound has been carried out in order to elucidate its molecular conformation. The molecular structure of the title compound is shown in Fig. 1. Bond lengths (Allen et al., 1987) and angles are within normal ranges. The dihedral angle between the mean planes of the two rings is 1.30 (4)°. In the crystal structure, intermolecular O—H···N hydrogen bonds (Table 1) link the molecules in chains along the b axis.

Related literature top

For related compounds containing a 2-(1H-imidazol-1-yl)-1-phenylethanol fragment, see: Porretta et al. (1993). For related structures, see: Tao et al. (2007); Liu et al. (2011). For standard bond lengths, see: Allen et al. (1987).

Experimental top

A mixture of 1-(4-fluorophenyl)-2-(1H-imidazol-1-yl)ethanone (2.04 g, 10 mol), sodium borohydride (0.756 g, 20 mmol) and 30 ml dry ethanol was refluxed for 3 h. After solvent evaporation, the mixture was neutralized with dilute hydrochloric acid and then refluxed for 30 min. After the mixture was cooled, the solution was alkalinized with sodium hydroxide, the precipitate was collected, recrystallized with ethanol, and a yellow deposit was obtain (m.p. 410–412 K). Crystals suitable for a X-ray analysis were obtained by dissolving the crude product (1.0 g) in ethanol (30 ml) and then allowing the solution to evaporate slowly at room temperature for about 7 d.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound viewed down the b axis. Hydrogen bonds are shown as dashed lines.

1-(4-Fluorophenyl)-2-(1H-imidazol-1-yl)ethanol top

Crystal data top

C₁₁H₁₁FN₂O	F(000) = 216
M_r = 206.22	D_x = 1.368 Mg m⁻³
Monoclinic, P2₁	Melting point: 410 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 7.1220 (14) Å	Cell parameters from 25 reflections
b = 5.4690 (11) Å	θ = 9–14°
c = 12.981 (3) Å	µ = 0.10 mm⁻¹
β = 98.13 (3)°	T = 293 K
V = 500.53 (19) Å³	Block, colourless
Z = 2	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	876 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 25.4°, θ_min = 1.6°
ω/2θ scans	h = 0→8
Absorption correction: multi-scan (North et al., 1968)	k = −6→6
T_min = 0.970, T_max = 0.990	l = −15→15
1992 measured reflections	3 standard reflections every 200 reflections
1024 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.090P)²] where P = (F_o² + 2F_c²)/3
1024 reflections	(Δ/σ)_max < 0.001
139 parameters	Δρ_max = 0.13 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₁H₁₁FN₂O	V = 500.53 (19) Å³
M_r = 206.22	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.1220 (14) Å	µ = 0.10 mm⁻¹
b = 5.4690 (11) Å	T = 293 K
c = 12.981 (3) Å	0.30 × 0.20 × 0.10 mm
β = 98.13 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	876 reflections with I > 2σ(I)
Absorption correction: multi-scan (North et al., 1968)	R_int = 0.029
T_min = 0.970, T_max = 0.990	3 standard reflections every 200 reflections
1992 measured reflections	intensity decay: 1%
1024 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.13 e Å⁻³
1024 reflections	Δρ_min = −0.18 e Å⁻³
139 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F	0.9055 (3)	0.3909 (5)	0.52854 (19)	0.0796 (8)
O	0.2786 (4)	−0.0461 (4)	0.19125 (18)	0.0557 (7)
H0A	0.275 (6)	−0.068 (9)	0.125 (3)	0.078*
N1	−0.0381 (3)	0.2845 (5)	0.16087 (19)	0.0445 (6)
C1	0.5787 (5)	0.4661 (7)	0.2920 (3)	0.0524 (8)
H1A	0.5509	0.5790	0.2384	0.063*
C2	0.7277 (5)	0.5097 (7)	0.3702 (3)	0.0575 (9)
H2A	0.8026	0.6486	0.3689	0.069*
N2	−0.2416 (4)	0.3439 (6)	0.0183 (2)	0.0558 (8)
C3	0.7627 (5)	0.3446 (7)	0.4495 (3)	0.0528 (9)
C4	0.6583 (5)	0.1347 (7)	0.4532 (3)	0.0554 (9)
H4A	0.6854	0.0246	0.5080	0.066*
C5	0.5115 (5)	0.0912 (7)	0.3732 (2)	0.0479 (8)
H5A	0.4397	−0.0507	0.3739	0.057*
C6	0.4702 (4)	0.2556 (6)	0.2925 (2)	0.0412 (7)
C7	0.3052 (4)	0.2069 (6)	0.2080 (2)	0.0426 (7)
H7A	0.3311	0.2836	0.1432	0.051*
C8	0.1259 (4)	0.3188 (7)	0.2395 (2)	0.0499 (8)
H8A	0.1010	0.2448	0.3041	0.060*
H8B	0.1460	0.4924	0.2518	0.060*
C9	−0.1609 (5)	0.0911 (7)	0.1518 (3)	0.0538 (9)
H9A	−0.1592	−0.0411	0.1970	0.065*
C10	−0.2855 (5)	0.1288 (8)	0.0645 (3)	0.0538 (9)
H10A	−0.3853	0.0254	0.0395	0.065*
C11	−0.0933 (5)	0.4306 (7)	0.0793 (3)	0.0518 (8)
H11A	−0.0336	0.5770	0.0672	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F	0.0595 (12)	0.0851 (18)	0.0844 (15)	0.0039 (12)	−0.0237 (11)	−0.0152 (13)
O	0.0673 (15)	0.0462 (14)	0.0498 (13)	0.0048 (12)	−0.0049 (12)	−0.0048 (11)
N1	0.0383 (13)	0.0482 (15)	0.0465 (14)	0.0036 (13)	0.0049 (11)	0.0024 (12)
C1	0.0580 (19)	0.0450 (19)	0.0544 (18)	0.0012 (16)	0.0083 (16)	0.0045 (15)
C2	0.050 (2)	0.0474 (18)	0.074 (2)	−0.0045 (16)	0.0051 (17)	−0.0051 (19)
N2	0.0467 (15)	0.065 (2)	0.0539 (15)	0.0065 (14)	0.0007 (12)	0.0065 (15)
C3	0.0438 (17)	0.054 (2)	0.0572 (19)	0.0073 (16)	−0.0035 (14)	−0.0126 (17)
C4	0.063 (2)	0.056 (2)	0.0449 (18)	0.0105 (18)	−0.0012 (15)	0.0034 (16)
C5	0.0486 (17)	0.0496 (19)	0.0452 (16)	0.0010 (16)	0.0057 (14)	0.0024 (15)
C6	0.0384 (15)	0.0433 (18)	0.0426 (16)	0.0063 (13)	0.0084 (12)	−0.0042 (13)
C7	0.0459 (16)	0.0440 (17)	0.0374 (15)	0.0043 (13)	0.0041 (13)	0.0003 (13)
C8	0.0492 (18)	0.053 (2)	0.0474 (17)	0.0050 (17)	0.0047 (14)	−0.0054 (16)
C9	0.0556 (19)	0.053 (2)	0.0545 (19)	−0.0056 (16)	0.0128 (16)	0.0074 (16)
C10	0.0409 (16)	0.066 (2)	0.0550 (18)	−0.0048 (16)	0.0077 (15)	−0.0031 (18)
C11	0.0437 (16)	0.0496 (19)	0.062 (2)	0.0009 (16)	0.0054 (15)	0.0104 (16)

Geometric parameters (Å, º) top

F—C3	1.362 (4)	C4—C5	1.387 (5)
O—C7	1.409 (5)	C4—H4A	0.9300
O—H0A	0.86 (4)	C5—C6	1.380 (5)
N1—C11	1.340 (4)	C5—H5A	0.9300
N1—C9	1.367 (5)	C6—C7	1.514 (4)
N1—C8	1.450 (4)	C7—C8	1.523 (4)
C1—C2	1.382 (5)	C7—H7A	0.9800
C1—C6	1.387 (5)	C8—H8A	0.9700
C1—H1A	0.9300	C8—H8B	0.9700
C2—C3	1.365 (5)	C9—C10	1.353 (5)
C2—H2A	0.9300	C9—H9A	0.9300
N2—C11	1.316 (4)	C10—H10A	0.9300
N2—C10	1.376 (5)	C11—H11A	0.9300
C3—C4	1.372 (6)

C7—O—H0A	106 (3)	C1—C6—C7	121.2 (3)
C11—N1—C9	106.3 (3)	O—C7—C6	111.0 (3)
C11—N1—C8	126.6 (3)	O—C7—C8	109.6 (3)
C9—N1—C8	127.0 (3)	C6—C7—C8	109.2 (2)
C2—C1—C6	120.6 (3)	O—C7—H7A	109.0
C2—C1—H1A	119.7	C6—C7—H7A	109.0
C6—C1—H1A	119.7	C8—C7—H7A	109.0
C3—C2—C1	118.6 (4)	N1—C8—C7	112.4 (3)
C3—C2—H2A	120.7	N1—C8—H8A	109.1
C1—C2—H2A	120.7	C7—C8—H8A	109.1
C11—N2—C10	105.0 (3)	N1—C8—H8B	109.1
C2—C3—F	118.8 (3)	C7—C8—H8B	109.1
C2—C3—C4	122.5 (3)	H8A—C8—H8B	107.9
F—C3—C4	118.6 (3)	C10—C9—N1	106.9 (3)
C3—C4—C5	118.2 (3)	C10—C9—H9A	126.6
C3—C4—H4A	120.9	N1—C9—H9A	126.6
C5—C4—H4A	120.9	C9—C10—N2	109.5 (3)
C6—C5—C4	120.9 (3)	C9—C10—H10A	125.3
C6—C5—H5A	119.5	N2—C10—H10A	125.3
C4—C5—H5A	119.5	N2—C11—N1	112.4 (3)
C5—C6—C1	119.1 (3)	N2—C11—H11A	123.8
C5—C6—C7	119.7 (3)	N1—C11—H11A	123.8

C6—C1—C2—C3	−1.7 (5)	C1—C6—C7—C8	−89.0 (3)
C1—C2—C3—F	−177.9 (3)	C11—N1—C8—C7	−87.2 (4)
C1—C2—C3—C4	1.5 (5)	C9—N1—C8—C7	89.0 (4)
C2—C3—C4—C5	−0.3 (5)	O—C7—C8—N1	−59.6 (4)
F—C3—C4—C5	179.0 (3)	C6—C7—C8—N1	178.6 (3)
C3—C4—C5—C6	−0.6 (5)	C11—N1—C9—C10	0.1 (3)
C4—C5—C6—C1	0.3 (5)	C8—N1—C9—C10	−176.7 (3)
C4—C5—C6—C7	−178.1 (3)	N1—C9—C10—N2	0.2 (4)
C2—C1—C6—C5	0.9 (5)	C11—N2—C10—C9	−0.5 (4)
C2—C1—C6—C7	179.3 (3)	C10—N2—C11—N1	0.6 (4)
C5—C6—C7—O	−31.6 (4)	C9—N1—C11—N2	−0.5 (4)
C1—C6—C7—O	150.0 (3)	C8—N1—C11—N2	176.3 (3)
C5—C6—C7—C8	89.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H0A···N2ⁱ	0.87 (4)	1.90 (4)	2.762 (4)	171 (5)

Symmetry code: (i) −x, y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁FN₂O
M_r	206.22
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	7.1220 (14), 5.4690 (11), 12.981 (3)
β (°)	98.13 (3)
V (Å³)	500.53 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Multi-scan (North et al., 1968)
T_min, T_max	0.970, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	1992, 1024, 876
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.124, 1.00
No. of reflections	1024
No. of parameters	139
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.18

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H0A···N2ⁱ	0.87 (4)	1.90 (4)	2.762 (4)	171 (5)

Symmetry code: (i) −x, y−1/2, −z.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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