2-Fluoro-N'-[(2-hydroxynaphthalen-1-yl)methylidene]benzohydrazide.

In the title mol-ecule, C(18)H(13)FN(2)O(2), the hy-droxy group is involved in an intra-molecular O-H⋯N hydrogen bond. The naphthyl ring system and the benzene ring form a dihedral angle of 31.0 (2)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [101].

Related literature

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011 ▶); Horiuchi et al. (2009 ▶). For coordination compounds with benzohydrazide ligands, see: El-Dissouky et al. (2010 ▶); Zhang et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the crystal structures of similar compounds, see: Suleiman Gwaram et al. (2010 ▶); Liu et al. (2011 ▶); Zhou et al. (2011 ▶); Meng et al. (2011 ▶).

Experimental

Crystal data

C18H13FN2O2

M = 308.30

Monoclinic,

a = 7.078 (3) Å

b = 29.1953 (16) Å

c = 7.3013 (10) Å

β = 106.521 (3)°

V = 1446.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.20 × 0.17 × 0.17 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.980, T max = 0.983

4745 measured reflections

2641 independent reflections

1777 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.133

S = 1.03

2641 reflections

212 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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) I, global. DOI: 10.1107/S1600536811050896/cv5206sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050896/cv5206Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050896/cv5206Isup3.cml

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

C18H13FN2O2	F(000) = 640
Mr = 308.30	Dx = 1.416 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 7.078 (3) Å	Cell parameters from 1565 reflections
b = 29.1953 (16) Å	θ = 2.7–24.3°
c = 7.3013 (10) Å	µ = 0.10 mm−1
β = 106.521 (3)°	T = 298 K
V = 1446.5 (6) Å3	Block, colourless
Z = 4	0.20 × 0.17 × 0.17 mm

Bruker SMART 1K CCD area-detector diffractometer	2641 independent reflections
Radiation source: fine-focus sealed tube	1777 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scan	θmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.980, Tmax = 0.983	k = −37→36
4745 measured reflections	l = −9→5

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.0478P] where P = (Fo2 + 2Fc2)/3
2641 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.18 e Å−3
3 restraints	Δρmin = −0.16 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	0.1283 (4)	0.37460 (7)	0.8168 (4)	0.0749 (7)
N1	0.1961 (4)	0.24093 (9)	0.8406 (4)	0.0472 (7)
N2	0.0468 (4)	0.20916 (9)	0.8074 (4)	0.0454 (7)
O1	0.0092 (3)	0.29182 (7)	0.6358 (3)	0.0568 (6)
O2	−0.3144 (4)	0.18598 (9)	0.7215 (4)	0.0626 (7)
H2	−0.2211	0.2032	0.7283	0.094*
C1	0.3335 (4)	0.31244 (10)	0.8066 (4)	0.0406 (7)
C2	0.3090 (5)	0.35837 (11)	0.8366 (5)	0.0498 (8)
C3	0.4602 (7)	0.38825 (14)	0.8874 (6)	0.0664 (11)
H3	0.4377	0.4191	0.9055	0.080*
C4	0.6445 (7)	0.37250 (16)	0.9116 (6)	0.0723 (13)
H4	0.7500	0.3927	0.9482	0.087*
C5	0.6796 (5)	0.32759 (16)	0.8836 (6)	0.0698 (12)
H5	0.8075	0.3173	0.8989	0.084*
C6	0.5243 (5)	0.29761 (13)	0.8327 (5)	0.0549 (9)
H6	0.5480	0.2668	0.8156	0.066*
C7	0.1631 (4)	0.28143 (10)	0.7509 (4)	0.0412 (7)
C8	0.0955 (5)	0.17013 (11)	0.8843 (5)	0.0427 (7)
H8	0.2266	0.1642	0.9488	0.051*
C9	−0.0507 (4)	0.13518 (11)	0.8723 (4)	0.0417 (7)
C10	−0.2470 (5)	0.14513 (12)	0.7981 (5)	0.0485 (8)
C11	−0.3917 (6)	0.11228 (14)	0.7994 (6)	0.0615 (10)
H11	−0.5245	0.1194	0.7495	0.074*
C12	−0.3365 (6)	0.07047 (14)	0.8733 (6)	0.0655 (11)
H12	−0.4334	0.0490	0.8733	0.079*
C13	−0.1387 (6)	0.05826 (11)	0.9502 (5)	0.0534 (9)
C14	−0.0837 (7)	0.01541 (13)	1.0315 (6)	0.0691 (11)
H14	−0.1810	−0.0060	1.0314	0.083*
C15	0.1059 (8)	0.00411 (13)	1.1100 (6)	0.0718 (12)
H15	0.1393	−0.0246	1.1645	0.086*
C16	0.2514 (6)	0.03585 (12)	1.1089 (5)	0.0641 (10)
H16	0.3832	0.0284	1.1635	0.077*
C17	0.2030 (5)	0.07762 (10)	1.0289 (5)	0.0505 (8)
H17	0.3030	0.0982	1.0272	0.061*
C18	0.0072 (5)	0.09071 (10)	0.9490 (4)	0.0436 (8)
H1	0.311 (4)	0.2354 (13)	0.931 (4)	0.080*

	U11	U22	U33	U12	U13	U23
F1	0.0780 (15)	0.0538 (12)	0.0873 (17)	0.0145 (11)	0.0145 (12)	0.0005 (11)
N1	0.0436 (15)	0.0432 (15)	0.0443 (17)	−0.0058 (11)	−0.0042 (12)	0.0034 (12)
N2	0.0497 (16)	0.0401 (15)	0.0415 (16)	−0.0063 (12)	0.0048 (12)	−0.0037 (12)
O1	0.0516 (14)	0.0480 (12)	0.0549 (16)	0.0006 (10)	−0.0108 (12)	0.0027 (11)
O2	0.0512 (13)	0.0647 (17)	0.0658 (17)	0.0022 (12)	0.0066 (12)	0.0068 (13)
C1	0.0448 (17)	0.0422 (17)	0.0290 (17)	0.0014 (13)	0.0011 (13)	0.0037 (13)
C2	0.059 (2)	0.0475 (19)	0.0366 (19)	0.0014 (17)	0.0041 (16)	0.0039 (15)
C3	0.087 (3)	0.053 (2)	0.049 (2)	−0.018 (2)	0.004 (2)	0.0039 (18)
C4	0.077 (3)	0.082 (3)	0.047 (2)	−0.037 (2)	0.000 (2)	0.014 (2)
C5	0.046 (2)	0.105 (3)	0.055 (2)	−0.009 (2)	0.0088 (18)	0.020 (2)
C6	0.048 (2)	0.069 (2)	0.046 (2)	0.0003 (17)	0.0103 (15)	0.0072 (17)
C7	0.0419 (17)	0.0411 (17)	0.0361 (18)	0.0043 (13)	0.0040 (15)	−0.0010 (14)
C8	0.0414 (16)	0.0457 (18)	0.0379 (18)	−0.0017 (13)	0.0060 (14)	−0.0039 (14)
C9	0.0494 (19)	0.0422 (18)	0.0318 (17)	−0.0057 (14)	0.0087 (14)	−0.0042 (13)
C10	0.0467 (19)	0.059 (2)	0.036 (2)	−0.0062 (15)	0.0065 (15)	−0.0045 (16)
C11	0.047 (2)	0.079 (3)	0.056 (2)	−0.0119 (18)	0.0103 (17)	−0.007 (2)
C12	0.066 (3)	0.075 (3)	0.058 (3)	−0.031 (2)	0.021 (2)	−0.012 (2)
C13	0.072 (2)	0.049 (2)	0.041 (2)	−0.0151 (17)	0.0197 (17)	−0.0073 (16)
C14	0.102 (3)	0.053 (2)	0.056 (3)	−0.024 (2)	0.029 (3)	−0.0059 (19)
C15	0.112 (4)	0.047 (2)	0.055 (3)	−0.005 (2)	0.022 (3)	0.0050 (18)
C16	0.079 (3)	0.057 (2)	0.052 (2)	0.007 (2)	0.0120 (19)	0.0018 (18)
C17	0.059 (2)	0.0412 (17)	0.049 (2)	0.0013 (16)	0.0116 (17)	0.0006 (15)
C18	0.0588 (19)	0.0397 (17)	0.0340 (18)	−0.0087 (14)	0.0159 (15)	−0.0080 (13)

F1—C2	1.332 (4)	C8—C9	1.438 (4)
N1—C7	1.339 (4)	C8—H8	0.9300
N1—N2	1.375 (3)	C9—C10	1.371 (4)
N1—H1	0.905 (10)	C9—C18	1.427 (4)
N2—C8	1.274 (4)	C10—C11	1.405 (5)
O1—C7	1.210 (4)	C11—C12	1.347 (5)
O2—C10	1.346 (4)	C11—H11	0.9300
O2—H2	0.8200	C12—C13	1.398 (5)
C1—C6	1.379 (5)	C12—H12	0.9300
C1—C2	1.378 (4)	C13—C14	1.392 (5)
C1—C7	1.470 (4)	C13—C18	1.403 (4)
C2—C3	1.348 (5)	C14—C15	1.341 (6)
C3—C4	1.347 (6)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.387 (6)
C4—C5	1.361 (6)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.353 (4)
C5—C6	1.371 (5)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.396 (5)
C6—H6	0.9300	C17—H17	0.9300
C7—N1—N2	119.4 (2)	C10—C9—C8	120.3 (3)
C7—N1—H1	121 (3)	C18—C9—C8	120.0 (3)
N2—N1—H1	120 (3)	O2—C10—C9	123.5 (3)
C8—N2—N1	115.4 (3)	O2—C10—C11	115.8 (3)
C10—O2—H2	109.5	C9—C10—C11	120.7 (3)
C6—C1—C2	116.5 (3)	C12—C11—C10	119.5 (4)
C6—C1—C7	122.6 (3)	C12—C11—H11	120.2
C2—C1—C7	120.9 (3)	C10—C11—H11	120.2
F1—C2—C3	117.5 (3)	C11—C12—C13	122.3 (3)
F1—C2—C1	119.3 (3)	C11—C12—H12	118.8
C3—C2—C1	123.2 (3)	C13—C12—H12	118.8
C4—C3—C2	118.6 (4)	C14—C13—C12	121.8 (4)
C4—C3—H3	120.7	C14—C13—C18	119.5 (4)
C2—C3—H3	120.7	C12—C13—C18	118.7 (3)
C3—C4—C5	121.4 (4)	C15—C14—C13	121.8 (4)
C3—C4—H4	119.3	C15—C14—H14	119.1
C5—C4—H4	119.3	C13—C14—H14	119.1
C4—C5—C6	119.3 (4)	C14—C15—C16	119.2 (4)
C4—C5—H5	120.3	C14—C15—H15	120.4
C6—C5—H5	120.3	C16—C15—H15	120.4
C5—C6—C1	121.0 (4)	C17—C16—C15	120.5 (4)
C5—C6—H6	119.5	C17—C16—H16	119.8
C1—C6—H6	119.5	C15—C16—H16	119.8
O1—C7—N1	123.9 (3)	C16—C17—C18	121.8 (3)
O1—C7—C1	122.9 (3)	C16—C17—H17	119.1
N1—C7—C1	113.2 (3)	C18—C17—H17	119.1
N2—C8—C9	120.5 (3)	C17—C18—C13	117.2 (3)
N2—C8—H8	119.7	C17—C18—C9	123.6 (3)
C9—C8—H8	119.7	C13—C18—C9	119.1 (3)
C10—C9—C18	119.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.91 (1)	1.91 (2)	2.785 (3)	163 (4)
O2—H2···N2	0.82	1.83	2.545 (4)	145.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.91 (1)	1.91 (2)	2.785 (3)	163 (4)
O2—H2⋯N2	0.82	1.83	2.545 (4)	145

Symmetry code: (i) .