(E)-(2,5-Difluoro-benz-yl)[(2-eth-oxy-naphthalen-1-yl)methyl-idene]amine.

In the title mol-ecule, C20H17F2NO, which adopts an E conformation with respect to the imine C=N double bond, the mean planes of the naphthalene ring system and the difluoro-phenyl ring form a dihedral angle of 85.82 (7)°. An intra-molecular C-H⋯N hydrogen bond occurs. In the crystal, weak C-H⋯F hydrogen bonds link the mol-ecules into zigzag chains along [010].

Related literature

For structural studies of Schiff bases by our group, see: Gül et al. (2007 ▶); Kantar et al. (2012 ▶); Kargılı et al. (2012 ▶); Pekdemir et al. (2012 ▶); Vesek et al. (2012 ▶). For classification of hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H17F2NO

M = 325.35

Monoclinic,

a = 12.5963 (8) Å

b = 14.3010 (8) Å

c = 9.8693 (8) Å

β = 108.672 (8)°

V = 1684.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.25 mm

Data collection

Oxford Diffraction SuperNova Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.703, T max = 1.000

5942 measured reflections

2958 independent reflections

1997 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.151

S = 1.06

2958 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001967/cv5376sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001967/cv5376Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001967/cv5376Isup3.cml

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

C20H17F2NO	F(000) = 680
Mr = 325.35	Dx = 1.283 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1869 reflections
a = 12.5963 (8) Å	θ = 3.3–29.3°
b = 14.3010 (8) Å	µ = 0.09 mm−1
c = 9.8693 (8) Å	T = 293 K
β = 108.672 (8)°	Block, yellow
V = 1684.3 (2) Å3	0.30 × 0.25 × 0.25 mm
Z = 4

Oxford Diffraction SuperNova Eos diffractometer	2958 independent reflections
Radiation source: fine-focus sealed tube	1997 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 16.0454 pixels mm-1	θmax = 25.0°, θmin = 3.3°
ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −17→17
Tmin = 0.703, Tmax = 1.000	l = −11→11
5942 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.5882P] where P = (Fo2 + 2Fc2)/3
2958 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.18 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
C1	0.05443 (18)	0.09513 (16)	0.9269 (2)	0.0475 (6)
C2	−0.04096 (19)	0.08982 (16)	0.8003 (3)	0.0505 (6)
C3	−0.0486 (2)	0.02790 (19)	0.6849 (3)	0.0648 (7)
H3	0.0107	−0.0121	0.6900	0.078*
C4	−0.1420 (3)	0.0264 (2)	0.5666 (3)	0.0792 (9)
H4	−0.1445	−0.0140	0.4918	0.095*
C5	−0.2335 (2)	0.0840 (2)	0.5559 (3)	0.0802 (9)
H5	−0.2967	0.0816	0.4750	0.096*
C6	−0.2300 (2)	0.1434 (2)	0.6633 (3)	0.0690 (8)
H6	−0.2917	0.1812	0.6561	0.083*
C7	−0.1346 (2)	0.14949 (18)	0.7868 (3)	0.0558 (6)
C8	−0.1289 (2)	0.2129 (2)	0.8967 (3)	0.0669 (7)
H8	−0.1897	0.2520	0.8879	0.080*
C9	−0.0383 (2)	0.21936 (19)	1.0152 (3)	0.0657 (7)
H9	−0.0369	0.2628	1.0859	0.079*
C10	0.0540 (2)	0.15986 (17)	1.0311 (3)	0.0529 (6)
C11	0.1491 (2)	0.2230 (2)	1.2652 (3)	0.0759 (8)
H11A	0.0884	0.2049	1.3004	0.091*
H11B	0.1386	0.2879	1.2353	0.091*
C12	0.2588 (3)	0.2110 (2)	1.3797 (3)	0.0938 (10)
H12A	0.2606	0.2491	1.4604	0.141*
H12B	0.3182	0.2296	1.3441	0.141*
H12C	0.2685	0.1466	1.4084	0.141*
C13	0.15149 (19)	0.03193 (16)	0.9571 (3)	0.0515 (6)
H13	0.1901	0.0185	1.0524	0.062*
C14	0.2785 (2)	−0.07076 (19)	0.9136 (3)	0.0690 (8)
H14A	0.2510	−0.1338	0.8875	0.083*
H14B	0.3083	−0.0676	1.0171	0.083*
C15	0.37095 (19)	−0.05036 (18)	0.8517 (3)	0.0578 (7)
C16	0.4542 (2)	−0.1146 (2)	0.8634 (3)	0.0749 (8)
C17	0.5395 (3)	−0.1034 (3)	0.8079 (4)	0.0963 (11)
H17	0.5931	−0.1499	0.8179	0.116*
C18	0.5443 (3)	−0.0221 (3)	0.7371 (4)	0.1016 (12)
H18	0.6008	−0.0124	0.6967	0.122*
C19	0.4647 (3)	0.0442 (3)	0.7271 (4)	0.0894 (10)
C20	0.3785 (2)	0.0321 (2)	0.7833 (3)	0.0738 (8)
H20	0.3259	0.0792	0.7750	0.089*
F1	0.45086 (15)	−0.19516 (13)	0.9363 (3)	0.1126 (7)
F2	0.46988 (19)	0.12570 (19)	0.6602 (3)	0.1524 (10)
N1	0.18605 (17)	−0.00533 (16)	0.8631 (2)	0.0647 (6)
O1	0.14961 (14)	0.16450 (12)	1.14686 (18)	0.0653 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0479 (13)	0.0437 (13)	0.0606 (14)	0.0002 (11)	0.0309 (11)	0.0012 (11)
C2	0.0504 (13)	0.0479 (13)	0.0615 (14)	−0.0059 (11)	0.0294 (11)	0.0034 (12)
C3	0.0580 (15)	0.0659 (17)	0.0731 (17)	−0.0086 (13)	0.0248 (13)	−0.0090 (14)
C4	0.0711 (19)	0.086 (2)	0.079 (2)	−0.0214 (17)	0.0224 (16)	−0.0187 (17)
C5	0.0602 (18)	0.094 (2)	0.080 (2)	−0.0175 (17)	0.0126 (15)	0.0027 (19)
C6	0.0533 (15)	0.0746 (18)	0.0803 (19)	−0.0004 (14)	0.0233 (14)	0.0203 (17)
C7	0.0538 (14)	0.0550 (15)	0.0662 (15)	0.0011 (12)	0.0299 (12)	0.0122 (13)
C8	0.0624 (16)	0.0677 (18)	0.0804 (19)	0.0171 (14)	0.0367 (15)	0.0094 (15)
C9	0.0726 (18)	0.0666 (17)	0.0673 (17)	0.0152 (15)	0.0356 (15)	−0.0071 (14)
C10	0.0554 (14)	0.0545 (15)	0.0566 (14)	0.0043 (12)	0.0289 (12)	0.0005 (12)
C11	0.083 (2)	0.080 (2)	0.0684 (18)	0.0049 (16)	0.0296 (15)	−0.0219 (16)
C12	0.091 (2)	0.105 (3)	0.079 (2)	0.006 (2)	0.0167 (17)	−0.0266 (19)
C13	0.0515 (13)	0.0468 (14)	0.0621 (14)	−0.0025 (11)	0.0265 (11)	−0.0008 (12)
C14	0.0623 (16)	0.0550 (16)	0.098 (2)	0.0051 (13)	0.0371 (15)	−0.0117 (15)
C15	0.0460 (13)	0.0582 (15)	0.0671 (16)	−0.0007 (12)	0.0152 (11)	−0.0197 (13)
C16	0.0596 (17)	0.0640 (18)	0.106 (2)	0.0023 (15)	0.0332 (16)	−0.0129 (17)
C17	0.0589 (19)	0.105 (3)	0.135 (3)	0.0102 (19)	0.044 (2)	−0.017 (2)
C18	0.062 (2)	0.142 (4)	0.112 (3)	−0.005 (2)	0.0430 (19)	−0.001 (3)
C19	0.067 (2)	0.103 (3)	0.096 (2)	−0.0109 (19)	0.0223 (17)	0.017 (2)
C20	0.0589 (16)	0.076 (2)	0.0832 (19)	0.0036 (15)	0.0179 (15)	−0.0035 (16)
F1	0.0883 (13)	0.0712 (12)	0.192 (2)	0.0199 (10)	0.0639 (14)	0.0089 (13)
F2	0.1138 (17)	0.161 (2)	0.186 (2)	−0.0072 (16)	0.0539 (17)	0.078 (2)
N1	0.0534 (12)	0.0723 (15)	0.0744 (14)	0.0099 (11)	0.0288 (11)	−0.0132 (12)
O1	0.0654 (11)	0.0716 (12)	0.0626 (11)	0.0083 (9)	0.0257 (9)	−0.0139 (9)

C1—C10	1.385 (3)	C11—H11B	0.9700
C1—C2	1.432 (3)	C12—H12A	0.9600
C1—C13	1.472 (3)	C12—H12B	0.9600
C2—C3	1.421 (3)	C12—H12C	0.9600
C2—C7	1.427 (3)	C13—N1	1.262 (3)
C3—C4	1.366 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—N1	1.452 (3)
C4—C5	1.394 (4)	C14—C15	1.507 (3)
C4—H4	0.9300	C14—H14A	0.9700
C5—C6	1.348 (4)	C14—H14B	0.9700
C5—H5	0.9300	C15—C16	1.371 (3)
C6—C7	1.414 (3)	C15—C20	1.377 (4)
C6—H6	0.9300	C16—C17	1.363 (4)
C7—C8	1.398 (4)	C16—F1	1.366 (3)
C8—C9	1.351 (4)	C17—C18	1.368 (5)
C8—H8	0.9300	C17—H17	0.9300
C9—C10	1.408 (3)	C18—C19	1.361 (5)
C9—H9	0.9300	C18—H18	0.9300
C10—O1	1.371 (3)	C19—F2	1.352 (4)
C11—O1	1.438 (3)	C19—C20	1.379 (4)
C11—C12	1.489 (4)	C20—H20	0.9300
C11—H11A	0.9700
C10—C1—C2	118.8 (2)	C11—C12—H12A	109.5
C10—C1—C13	117.4 (2)	C11—C12—H12B	109.5
C2—C1—C13	123.7 (2)	H12A—C12—H12B	109.5
C3—C2—C7	117.1 (2)	C11—C12—H12C	109.5
C3—C2—C1	123.7 (2)	H12A—C12—H12C	109.5
C7—C2—C1	119.2 (2)	H12B—C12—H12C	109.5
C4—C3—C2	120.9 (3)	N1—C13—C1	124.7 (2)
C4—C3—H3	119.5	N1—C13—H13	117.6
C2—C3—H3	119.5	C1—C13—H13	117.6
C3—C4—C5	121.3 (3)	N1—C14—C15	112.0 (2)
C3—C4—H4	119.3	N1—C14—H14A	109.2
C5—C4—H4	119.3	C15—C14—H14A	109.2
C6—C5—C4	119.7 (3)	N1—C14—H14B	109.2
C6—C5—H5	120.2	C15—C14—H14B	109.2
C4—C5—H5	120.2	H14A—C14—H14B	107.9
C5—C6—C7	121.4 (3)	C16—C15—C20	116.4 (3)
C5—C6—H6	119.3	C16—C15—C14	120.4 (3)
C7—C6—H6	119.3	C20—C15—C14	123.3 (2)
C8—C7—C6	121.8 (2)	C17—C16—F1	118.2 (3)
C8—C7—C2	118.7 (2)	C17—C16—C15	124.6 (3)
C6—C7—C2	119.6 (2)	F1—C16—C15	117.3 (3)
C9—C8—C7	122.4 (2)	C16—C17—C18	118.4 (3)
C9—C8—H8	118.8	C16—C17—H17	120.8
C7—C8—H8	118.8	C18—C17—H17	120.8
C8—C9—C10	119.6 (2)	C19—C18—C17	118.5 (3)
C8—C9—H9	120.2	C19—C18—H18	120.8
C10—C9—H9	120.2	C17—C18—H18	120.8
O1—C10—C1	116.1 (2)	F2—C19—C18	119.1 (3)
O1—C10—C9	122.5 (2)	F2—C19—C20	118.2 (3)
C1—C10—C9	121.4 (2)	C18—C19—C20	122.7 (3)
O1—C11—C12	107.7 (2)	C15—C20—C19	119.5 (3)
O1—C11—H11A	110.2	C15—C20—H20	120.3
C12—C11—H11A	110.2	C19—C20—H20	120.3
O1—C11—H11B	110.2	C13—N1—C14	116.6 (2)
C12—C11—H11B	110.2	C10—O1—C11	118.26 (19)
H11A—C11—H11B	108.5
C10—C1—C2—C3	178.3 (2)	C8—C9—C10—C1	0.6 (4)
C13—C1—C2—C3	−5.1 (3)	C10—C1—C13—N1	−153.0 (2)
C10—C1—C2—C7	−1.6 (3)	C2—C1—C13—N1	30.4 (3)
C13—C1—C2—C7	175.0 (2)	N1—C14—C15—C16	−166.9 (2)
C7—C2—C3—C4	0.1 (4)	N1—C14—C15—C20	14.0 (4)
C1—C2—C3—C4	−179.8 (2)	C20—C15—C16—C17	−2.6 (4)
C2—C3—C4—C5	−1.1 (4)	C14—C15—C16—C17	178.3 (3)
C3—C4—C5—C6	0.7 (5)	C20—C15—C16—F1	177.2 (2)
C4—C5—C6—C7	0.8 (4)	C14—C15—C16—F1	−1.9 (4)
C5—C6—C7—C8	178.0 (3)	F1—C16—C17—C18	−178.8 (3)
C5—C6—C7—C2	−1.8 (4)	C15—C16—C17—C18	1.0 (5)
C3—C2—C7—C8	−178.5 (2)	C16—C17—C18—C19	0.9 (5)
C1—C2—C7—C8	1.4 (3)	C17—C18—C19—F2	178.6 (3)
C3—C2—C7—C6	1.3 (3)	C17—C18—C19—C20	−1.1 (5)
C1—C2—C7—C6	−178.8 (2)	C16—C15—C20—C19	2.2 (4)
C6—C7—C8—C9	179.9 (3)	C14—C15—C20—C19	−178.7 (3)
C2—C7—C8—C9	−0.3 (4)	F2—C19—C20—C15	179.8 (3)
C7—C8—C9—C10	−0.8 (4)	C18—C19—C20—C15	−0.5 (5)
C2—C1—C10—O1	−177.18 (19)	C1—C13—N1—C14	−175.9 (2)
C13—C1—C10—O1	6.1 (3)	C15—C14—N1—C13	−130.8 (2)
C2—C1—C10—C9	0.6 (3)	C1—C10—O1—C11	−173.3 (2)
C13—C1—C10—C9	−176.2 (2)	C9—C10—O1—C11	9.0 (3)
C8—C9—C10—O1	178.2 (2)	C12—C11—O1—C10	176.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1	0.93	2.32	2.955 (3)	125
C6—H6···F1i	0.93	2.61	3.505 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1	0.93	2.32	2.955 (3)	125
C6—H6⋯F1i	0.93	2.61	3.505 (4)	162

Symmetry code: (i) .