4-[(E)-(4-Fluoro-benzyl-idene)amino]-phenol.

In the title compound, C(13)H(10)FNO, the dihedral angle between the aromatic rings is 55.60 (8)°. In the crystal, mol-ecules 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 = 215.22

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.09

1935 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811019921/hb5896sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811019921/hb5896Isup3.cml

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

C13H10FNO	F(000) = 448
Mr = 215.22	Dx = 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

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

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(Fo2) + (0.0422P)2 + 0.3813P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1935 reflections	Δρmax = 0.18 e Å−3
147 parameters	Δρmin = −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)

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
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*

	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)

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)

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

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) .