4-[(E)-(4-Fluoro­benzyl­idene)amino]­phenol

Sun, L.-X.; Yu, Y.-D.; Wei, G.-Y.

doi:10.1107/S1600536811019921

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1578

doi:10.1107/S1600536811019921

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4-[(E)-(4-Fluorobenzylidene)amino]phenol

Li-Xia Sun,^a Yun-Dan Yu ^a and Guo-Ying Wei ^a ^*

^aCollege of Materials Science & Engineering, China Jiliang University, Hangzhou 310053, People's Republic of China
^*Correspondence e-mail: nanocrystal11@163.com

(Received 25 May 2011; accepted 25 May 2011; online 4 June 2011)

In the title compound, C₁₃H₁₀FNO, the dihedral angle between the aromatic rings is 55.60 (8)°. In the crystal, molecules are linked by O—H—N hydrogen bonds, forming zigzag C(7) chains propagating in [101].

Related literature

For a related structure and background references, see: Sun et al. (2011 ). For related structures, see: Nie et al. (2008 ); Fun et al. (2008 ); Alhadi et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₀FNO
M_r = 215.22
Monoclinic, P 2₁ /n
a = 9.400 (5) Å
b = 12.213 (7) Å
c = 9.450 (5) Å
β = 104.666 (5)°
V = 1049.5 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.25 × 0.23 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.976, T_max = 0.979
5880 measured reflections
1935 independent reflections
1474 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.116
S = 1.09
1935 reflections
147 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1ⁱ	0.82	2.09	2.885 (2)	163
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019921/hb5896sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019921/hb5896Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019921/hb5896Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of Schiff bases (Sun et al., 2011), we report here the crystal structure of the title compound, (I). In (I) (Fig. 1), the bond lengths and angles are normal and comparable to the values observed in similar compounds (Nie et al., 2008; Fun et al., 2008; Alhadi et al., 2008). The dihedral angle between the two aromatic rings in the Schiff base molecule is 55.6 °, indicating that two these rings are not coplanar. Intermolecular O-H—N hydrogen bonds (Table 1) link the molecules along a axis (Fig. 2).

Related literature top

For a related structure and background references, see: Sun et al. (2011). For related structures, see: Nie et al. (2008); Fun et al. (2008); Alhadi et al. (2008).

Experimental top

A mixture of 4-chlorobenzaldehyde (5 mmol), 4-aminophenol (5 mmol) and methanol (40 ml) was refluxed for 2 h. It was then allowed to cool and filtered. Recrystallization of the crude product from methanol yielded yellow blocks of (I).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compounds with 50% probability displacement ellipsoids for non-hydrogen atoms.
	Fig. 2. Molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

4-[(E)-(4-Fluorobenzylidene)amino]phenol top

Crystal data top

C₁₃H₁₀FNO	F(000) = 448
M_r = 215.22	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2754 reflections
a = 9.400 (5) Å	θ = 2.7–28.2°
b = 12.213 (7) Å	µ = 0.10 mm⁻¹
c = 9.450 (5) Å	T = 296 K
β = 104.666 (5)°	Block, yellow
V = 1049.5 (10) Å³	0.25 × 0.23 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1935 independent reflections
Radiation source: fine-focus sealed tube	1474 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→11
T_min = 0.976, T_max = 0.979	k = −11→14
5880 measured reflections	l = −11→11

Refinement top

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0422P)² + 0.3813P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
1935 reflections	Δρ_max = 0.18 e Å⁻³
147 parameters	Δρ_min = −0.19 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: 0.077 (5)

Crystal data top

C₁₃H₁₀FNO	V = 1049.5 (10) Å³
M_r = 215.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.400 (5) Å	µ = 0.10 mm⁻¹
b = 12.213 (7) Å	T = 296 K
c = 9.450 (5) Å	0.25 × 0.23 × 0.22 mm
β = 104.666 (5)°

Data collection top

Bruker APEXII CCD diffractometer	1935 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1474 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.979	R_int = 0.036
5880 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.09	Δρ_max = 0.18 e Å⁻³
1935 reflections	Δρ_min = −0.19 e Å⁻³
147 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
C1	0.3906 (2)	0.14260 (14)	0.6005 (2)	0.0440 (5)
C2	0.4887 (2)	0.22747 (14)	0.63956 (18)	0.0409 (4)
H2	0.5876	0.2139	0.6826	0.049*
C3	0.43732 (19)	0.33301 (14)	0.61347 (18)	0.0368 (4)
H3	0.5019	0.3915	0.6400	0.044*
C4	0.28916 (18)	0.35297 (12)	0.54763 (17)	0.0327 (4)
C5	0.1950 (2)	0.26412 (14)	0.50840 (18)	0.0383 (4)
H5	0.0962	0.2765	0.4636	0.046*
C6	0.2447 (2)	0.15804 (14)	0.5344 (2)	0.0451 (5)
H6	0.1812	0.0989	0.5079	0.054*
C7	0.22867 (19)	0.46193 (13)	0.50988 (18)	0.0355 (4)
H7	0.1338	0.4662	0.4497	0.043*
C8	0.22355 (17)	0.65015 (12)	0.48809 (17)	0.0317 (4)
C9	0.22777 (18)	0.74242 (13)	0.57483 (17)	0.0343 (4)
H9	0.2750	0.7392	0.6739	0.041*
C10	0.16262 (19)	0.83889 (13)	0.51566 (18)	0.0373 (4)
H10	0.1647	0.8998	0.5752	0.045*
C11	0.09399 (18)	0.84530 (13)	0.36764 (18)	0.0354 (4)
C12	0.09253 (18)	0.75496 (14)	0.27921 (18)	0.0363 (4)
H12	0.0489	0.7595	0.1794	0.044*
C13	0.15602 (19)	0.65777 (13)	0.33919 (18)	0.0362 (4)
H13	0.1536	0.5969	0.2794	0.043*
N1	0.29403 (15)	0.55196 (11)	0.55190 (14)	0.0344 (4)
F1	0.44178 (15)	0.03938 (9)	0.62945 (16)	0.0739 (4)
O1	0.03080 (16)	0.94277 (10)	0.31471 (14)	0.0520 (4)
H1A	−0.0279	0.9327	0.2353	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0595 (12)	0.0274 (9)	0.0470 (10)	0.0055 (8)	0.0167 (9)	0.0046 (7)
C2	0.0407 (10)	0.0414 (10)	0.0392 (9)	0.0064 (8)	0.0077 (8)	0.0005 (7)
C3	0.0408 (10)	0.0324 (9)	0.0371 (9)	−0.0032 (7)	0.0096 (7)	−0.0048 (7)
C4	0.0393 (9)	0.0291 (9)	0.0298 (8)	−0.0013 (7)	0.0089 (7)	0.0004 (6)
C5	0.0402 (10)	0.0359 (10)	0.0371 (9)	−0.0045 (7)	0.0064 (7)	0.0029 (7)
C6	0.0550 (12)	0.0302 (10)	0.0494 (10)	−0.0093 (8)	0.0117 (9)	−0.0002 (8)
C7	0.0350 (9)	0.0327 (9)	0.0371 (9)	−0.0010 (7)	0.0061 (7)	0.0017 (7)
C8	0.0314 (9)	0.0279 (9)	0.0346 (8)	−0.0006 (6)	0.0065 (7)	0.0036 (6)
C9	0.0371 (9)	0.0333 (9)	0.0295 (8)	−0.0027 (7)	0.0031 (7)	0.0009 (7)
C10	0.0427 (10)	0.0278 (9)	0.0390 (9)	−0.0022 (7)	0.0060 (7)	−0.0026 (7)
C11	0.0352 (9)	0.0279 (9)	0.0405 (9)	−0.0013 (7)	0.0049 (7)	0.0058 (7)
C12	0.0394 (10)	0.0374 (10)	0.0292 (8)	−0.0013 (7)	0.0033 (7)	0.0025 (7)
C13	0.0410 (10)	0.0318 (9)	0.0344 (9)	−0.0011 (7)	0.0070 (7)	−0.0035 (7)
N1	0.0380 (8)	0.0291 (8)	0.0345 (7)	0.0009 (6)	0.0064 (6)	0.0020 (6)
F1	0.0840 (10)	0.0317 (7)	0.1022 (10)	0.0132 (6)	0.0167 (8)	0.0105 (6)
O1	0.0641 (9)	0.0294 (7)	0.0508 (8)	0.0039 (6)	−0.0071 (6)	0.0060 (5)

Geometric parameters (Å, º) top

C1—F1	1.352 (2)	C8—C9	1.388 (2)
C1—C6	1.368 (3)	C8—C13	1.392 (2)
C1—C2	1.374 (3)	C8—N1	1.428 (2)
C2—C3	1.377 (2)	C9—C10	1.379 (2)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.395 (2)	C10—C11	1.386 (2)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.390 (2)	C11—O1	1.367 (2)
C4—C7	1.456 (2)	C11—C12	1.382 (2)
C5—C6	1.378 (2)	C12—C13	1.384 (2)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—N1	1.273 (2)	O1—H1A	0.8200
C7—H7	0.9300

F1—C1—C6	118.99 (17)	C9—C8—C13	118.68 (14)
F1—C1—C2	117.95 (17)	C9—C8—N1	119.45 (14)
C6—C1—C2	123.06 (16)	C13—C8—N1	121.80 (14)
C1—C2—C3	118.47 (17)	C10—C9—C8	120.71 (15)
C1—C2—H2	120.8	C10—C9—H9	119.6
C3—C2—H2	120.8	C8—C9—H9	119.6
C2—C3—C4	120.59 (16)	C9—C10—C11	120.18 (15)
C2—C3—H3	119.7	C9—C10—H10	119.9
C4—C3—H3	119.7	C11—C10—H10	119.9
C5—C4—C3	118.60 (15)	O1—C11—C12	122.48 (15)
C5—C4—C7	117.74 (15)	O1—C11—C10	117.79 (15)
C3—C4—C7	123.56 (15)	C12—C11—C10	119.73 (15)
C6—C5—C4	121.46 (17)	C13—C12—C11	119.99 (15)
C6—C5—H5	119.3	C13—C12—H12	120.0
C4—C5—H5	119.3	C11—C12—H12	120.0
C1—C6—C5	117.80 (16)	C12—C13—C8	120.68 (15)
C1—C6—H6	121.1	C12—C13—H13	119.7
C5—C6—H6	121.1	C8—C13—H13	119.7
N1—C7—C4	125.84 (15)	C7—N1—C8	117.26 (14)
N1—C7—H7	117.1	C11—O1—H1A	109.5
C4—C7—H7	117.1

F1—C1—C2—C3	−178.66 (16)	N1—C8—C9—C10	178.98 (15)
C6—C1—C2—C3	1.3 (3)	C8—C9—C10—C11	−1.1 (3)
C1—C2—C3—C4	−0.6 (3)	C9—C10—C11—O1	179.82 (16)
C2—C3—C4—C5	−0.3 (2)	C9—C10—C11—C12	−0.7 (3)
C2—C3—C4—C7	−176.69 (15)	O1—C11—C12—C13	−178.88 (16)
C3—C4—C5—C6	0.6 (3)	C10—C11—C12—C13	1.7 (3)
C7—C4—C5—C6	177.20 (16)	C11—C12—C13—C8	−0.9 (3)
F1—C1—C6—C5	178.95 (16)	C9—C8—C13—C12	−0.9 (3)
C2—C1—C6—C5	−1.0 (3)	N1—C8—C13—C12	−177.93 (16)
C4—C5—C6—C1	0.0 (3)	C4—C7—N1—C8	172.19 (15)
C5—C4—C7—N1	171.35 (17)	C9—C8—N1—C7	140.76 (16)
C3—C4—C7—N1	−12.2 (3)	C13—C8—N1—C7	−42.2 (2)
C13—C8—C9—C10	1.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.82	2.09	2.885 (2)	163

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀FNO
M_r	215.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.400 (5), 12.213 (7), 9.450 (5)
β (°)	104.666 (5)
V (Å³)	1049.5 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.23 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.976, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	5880, 1935, 1474
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.116, 1.09
No. of reflections	1935
No. of parameters	147
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.82	2.09	2.885 (2)	163

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

Acknowledgements

This project was supported by Zhejiang Provincial Natural Science Foundation of China (grant No. Y4110290).

References

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