4-Fluoro-N-[(E)-3,4,5-tri-meth-oxy-benzyl-idene]aniline.

The title compound, C16H16FNO3, exists in a trans configuration with respect to the C=N bond [1.258 (2) Å]. The central meth-oxy O atom deviates from the plane of the attached benzene ring by 0.0911 (14) Å. The dihedral angle between the aromatic rings is 47.58 (11)°. The crystal structure features C-H⋯N and C-H⋯O inter-actions.

Related literature

For the uses and biological importance of Schiff base compounds, see: Xia et al. (2009 ▶); Shah et al. (1992 ▶); Ünver et al. (2004 ▶). For related structures, see: Fun et al. (2011 ▶); Khalaji & Simpson (2009 ▶); Balachandar et al. (2013 ▶).

Experimental

Crystal data

C16H16FNO3

M = 289.30

Monoclinic,

a = 7.1147 (9) Å

b = 8.3841 (9) Å

c = 12.9217 (13) Å

β = 105.266 (5)°

V = 743.59 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.40 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.962, T max = 0.971

5699 measured reflections

3358 independent reflections

2468 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.128

S = 1.00

3358 reflections

190 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813017741/ds2233sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017741/ds2233Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813017741/ds2233Isup3.cml

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

C16H16FNO3	F(000) = 304
Mr = 289.30	Dx = 1.292 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2468 reflections
a = 7.1147 (9) Å	θ = 2.9–28.3°
b = 8.3841 (9) Å	µ = 0.10 mm−1
c = 12.9217 (13) Å	T = 296 K
β = 105.266 (5)°	Block, colourless
V = 743.59 (14) Å3	0.40 × 0.35 × 0.30 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	3358 independent reflections
Radiation source: fine-focus sealed tube	2468 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ω and φ scan	θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −6→9
Tmin = 0.962, Tmax = 0.971	k = −11→11
5699 measured reflections	l = −17→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0767P)2 + 0.017P] where P = (Fo2 + 2Fc2)/3
3358 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.13 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	0.9942 (4)	0.5751 (3)	0.51013 (17)	0.1191 (7)
N1	0.4847 (3)	0.2770 (2)	0.70169 (14)	0.0557 (4)
O3	0.0659 (2)	−0.05790 (17)	1.02505 (12)	0.0596 (4)
C4	0.6764 (5)	0.5185 (4)	0.5155 (2)	0.0901 (9)
H4	0.6295	0.5810	0.4548	0.108*
O5	−0.0273 (2)	−0.0800 (2)	0.81378 (13)	0.0745 (5)
O6	0.3531 (2)	0.12728 (18)	1.13224 (11)	0.0608 (4)
C3	0.8696 (5)	0.5003 (3)	0.5578 (2)	0.0763 (7)
C2	0.9455 (4)	0.4108 (4)	0.6458 (2)	0.0737 (7)
H2	1.0795	0.3987	0.6724	0.088*
C6	0.6199 (3)	0.3532 (3)	0.65551 (15)	0.0530 (5)
C7	0.5225 (3)	0.2666 (2)	0.80220 (16)	0.0474 (4)
H7	0.6363	0.3137	0.8430	0.057*
C8	0.3977 (3)	0.1847 (2)	0.85798 (15)	0.0453 (4)
C13	0.4394 (3)	0.1984 (2)	0.96847 (15)	0.0465 (4)
H13	0.5447	0.2598	1.0053	0.056*
C11	0.1708 (3)	0.0279 (2)	0.96978 (16)	0.0482 (4)
C1	0.8184 (3)	0.3381 (3)	0.69503 (18)	0.0605 (6)
H1	0.8679	0.2774	0.7564	0.073*
C12	0.3258 (3)	0.1214 (2)	1.02398 (15)	0.0468 (4)
C15	−0.0943 (4)	0.0258 (3)	1.0437 (2)	0.0794 (7)
H15A	−0.1612	−0.0411	1.0827	0.119*
H15B	−0.1819	0.0552	0.9763	0.119*
H15C	−0.0488	0.1201	1.0847	0.119*
C5	0.5502 (4)	0.4435 (4)	0.56337 (18)	0.0777 (7)
H5	0.4166	0.4532	0.5338	0.093*
C9	0.2415 (3)	0.0927 (2)	0.80236 (17)	0.0513 (5)
H9	0.2132	0.0838	0.7281	0.062*
C10	0.1283 (3)	0.0142 (2)	0.85863 (16)	0.0513 (5)
C14	−0.0696 (4)	−0.1114 (4)	0.7021 (2)	0.0955 (10)
H14A	−0.1824	−0.1788	0.6812	0.143*
H14B	0.0396	−0.1639	0.6864	0.143*
H14C	−0.0948	−0.0128	0.6632	0.143*
C16	0.5085 (4)	0.2205 (4)	1.1925 (2)	0.0863 (8)
H16A	0.5116	0.2145	1.2671	0.129*
H16B	0.4905	0.3294	1.1691	0.129*
H16C	0.6291	0.1811	1.1824	0.129*

	U11	U22	U33	U12	U13	U23
F1	0.1440 (16)	0.1259 (17)	0.1116 (12)	−0.0088 (14)	0.0766 (12)	0.0330 (12)
N1	0.0526 (10)	0.0608 (10)	0.0501 (9)	−0.0022 (8)	0.0073 (7)	−0.0009 (8)
O3	0.0550 (8)	0.0458 (8)	0.0784 (10)	−0.0049 (6)	0.0179 (7)	0.0129 (7)
C4	0.115 (3)	0.096 (2)	0.0619 (14)	0.0216 (18)	0.0283 (15)	0.0319 (15)
O5	0.0697 (10)	0.0754 (11)	0.0697 (9)	−0.0290 (9)	0.0030 (8)	−0.0048 (9)
O6	0.0667 (9)	0.0585 (9)	0.0548 (8)	−0.0136 (7)	0.0117 (7)	0.0029 (7)
C3	0.103 (2)	0.0727 (16)	0.0654 (15)	0.0007 (14)	0.0434 (15)	0.0111 (12)
C2	0.0710 (15)	0.0847 (18)	0.0699 (14)	0.0018 (13)	0.0266 (12)	0.0071 (13)
C6	0.0614 (13)	0.0531 (11)	0.0437 (10)	0.0027 (9)	0.0125 (9)	−0.0014 (9)
C7	0.0448 (10)	0.0406 (10)	0.0540 (11)	0.0010 (8)	0.0077 (8)	−0.0028 (8)
C8	0.0416 (9)	0.0364 (9)	0.0562 (11)	0.0053 (7)	0.0097 (8)	0.0019 (8)
C13	0.0425 (9)	0.0379 (9)	0.0558 (11)	−0.0014 (7)	0.0071 (8)	−0.0019 (8)
C11	0.0445 (10)	0.0345 (9)	0.0638 (11)	0.0031 (8)	0.0111 (9)	0.0074 (8)
C1	0.0630 (14)	0.0647 (13)	0.0543 (12)	0.0057 (10)	0.0164 (10)	0.0139 (10)
C12	0.0481 (10)	0.0363 (9)	0.0546 (11)	0.0033 (8)	0.0110 (8)	0.0039 (8)
C15	0.0658 (15)	0.0681 (16)	0.113 (2)	−0.0018 (12)	0.0385 (14)	0.0099 (14)
C5	0.0791 (15)	0.099 (2)	0.0506 (12)	0.0123 (15)	0.0093 (11)	0.0191 (13)
C9	0.0511 (10)	0.0456 (10)	0.0522 (10)	0.0007 (8)	0.0047 (8)	−0.0010 (8)
C10	0.0454 (10)	0.0378 (10)	0.0650 (12)	−0.0016 (8)	0.0049 (9)	0.0012 (9)
C14	0.0864 (19)	0.102 (2)	0.0858 (18)	−0.0330 (17)	0.0016 (16)	−0.0256 (17)
C16	0.097 (2)	0.097 (2)	0.0620 (14)	−0.0355 (17)	0.0170 (14)	−0.0132 (14)

F1—C3	1.359 (3)	C8—C13	1.384 (3)
N1—C7	1.258 (2)	C8—C9	1.388 (3)
N1—C6	1.411 (3)	C13—C12	1.375 (3)
O3—C11	1.366 (2)	C13—H13	0.9300
O3—C15	1.412 (3)	C11—C12	1.384 (2)
C4—C3	1.347 (4)	C11—C10	1.392 (3)
C4—C5	1.370 (4)	C1—H1	0.9300
C4—H4	0.9300	C15—H15A	0.9600
O5—C10	1.359 (2)	C15—H15B	0.9600
O5—C14	1.419 (3)	C15—H15C	0.9600
O6—C12	1.362 (2)	C5—H5	0.9300
O6—C16	1.409 (3)	C9—C10	1.386 (3)
C3—C2	1.351 (4)	C9—H9	0.9300
C2—C1	1.378 (3)	C14—H14A	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C6—C1	1.375 (3)	C14—H14C	0.9600
C6—C5	1.388 (3)	C16—H16A	0.9600
C7—C8	1.455 (3)	C16—H16B	0.9600
C7—H7	0.9300	C16—H16C	0.9600
C7—N1—C6	118.93 (17)	O6—C12—C13	125.09 (17)
C11—O3—C15	113.85 (16)	O6—C12—C11	114.78 (16)
C3—C4—C5	119.0 (2)	C13—C12—C11	120.13 (17)
C3—C4—H4	120.5	O3—C15—H15A	109.5
C5—C4—H4	120.5	O3—C15—H15B	109.5
C10—O5—C14	118.18 (19)	H15A—C15—H15B	109.5
C12—O6—C16	117.81 (17)	O3—C15—H15C	109.5
C4—C3—C2	122.9 (3)	H15A—C15—H15C	109.5
C4—C3—F1	118.8 (2)	H15B—C15—H15C	109.5
C2—C3—F1	118.3 (3)	C4—C5—C6	120.6 (3)
C3—C2—C1	117.9 (2)	C4—C5—H5	119.7
C3—C2—H2	121.0	C6—C5—H5	119.7
C1—C2—H2	121.0	C10—C9—C8	119.28 (18)
C1—C6—C5	117.9 (2)	C10—C9—H9	120.4
C1—C6—N1	123.28 (19)	C8—C9—H9	120.4
C5—C6—N1	118.7 (2)	O5—C10—C9	124.98 (18)
N1—C7—C8	123.50 (17)	O5—C10—C11	114.75 (18)
N1—C7—H7	118.3	C9—C10—C11	120.27 (17)
C8—C7—H7	118.3	O5—C14—H14A	109.5
C13—C8—C9	120.36 (17)	O5—C14—H14B	109.5
C13—C8—C7	118.60 (16)	H14A—C14—H14B	109.5
C9—C8—C7	121.03 (17)	O5—C14—H14C	109.5
C12—C13—C8	120.21 (16)	H14A—C14—H14C	109.5
C12—C13—H13	119.9	H14B—C14—H14C	109.5
C8—C13—H13	119.9	O6—C16—H16A	109.5
O3—C11—C12	120.42 (17)	O6—C16—H16B	109.5
O3—C11—C10	119.75 (17)	H16A—C16—H16B	109.5
C12—C11—C10	119.73 (17)	O6—C16—H16C	109.5
C6—C1—C2	121.5 (2)	H16A—C16—H16C	109.5
C6—C1—H1	119.2	H16B—C16—H16C	109.5
C2—C1—H1	119.2

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N1i	0.93	2.57	3.492 (3)	174
C7—H7···O3ii	0.93	2.58	3.504 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N1i	0.93	2.57	3.492 (3)	174
C7—H7⋯O3ii	0.93	2.58	3.504 (3)	173

Symmetry codes: (i) ; (ii) .