(E)-N'-(3-Fluoro-benzyl-idene)-4-methyl-benzohydrazide.

In the title compound, C(15)H(13)FN(2)O, the dihedral angle between the benzene rings is 16.9 (2)°. The F atom and the O atom are in a syn conformation. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds to generate C(4) chains propagating along the b-axis direction.

Related literature

For hydrazones that we have reported previously, see: Liu & You (2010 ▶); Liu & Wang (2010 ▶). For the crystal structures of other similar hydrazone compounds, see: Vijayakumar et al. (2009 ▶); Xu et al. (2009 ▶); Shafiq et al. (2009 ▶).

Experimental

Crystal data

C15H13FN2O

M = 256.27

Orthorhombic,

a = 13.2629 (5) Å

b = 7.9118 (3) Å

c = 24.9235 (8) Å

V = 2615.31 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.984, T max = 0.986

26269 measured reflections

2424 independent reflections

1997 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.123

S = 1.04

2424 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019484/hb6775sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019484/hb6775Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019484/hb6775Isup3.cml

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

C15H13FN2O	Dx = 1.302 Mg m−3
Mr = 256.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 12661 reflections
a = 13.2629 (5) Å	θ = 2.4–26.6°
b = 7.9118 (3) Å	µ = 0.09 mm−1
c = 24.9235 (8) Å	T = 298 K
V = 2615.31 (16) Å3	Block, colourless
Z = 8	0.17 × 0.15 × 0.15 mm
F(000) = 1072

Bruker SMART CCD diffractometer	2424 independent reflections
Radiation source: fine-focus sealed tube	1997 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→16
Tmin = 0.984, Tmax = 0.986	k = −9→9
26269 measured reflections	l = −26→30

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0664P)2 + 0.6653P] where P = (Fo2 + 2Fc2)/3
2424 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.78383 (10)	1.16955 (17)	0.83669 (4)	0.0913 (4)
N1	0.77048 (10)	0.87893 (16)	0.65528 (5)	0.0465 (3)
N2	0.74744 (10)	0.79810 (16)	0.60759 (5)	0.0479 (3)
O1	0.63068 (8)	0.99556 (13)	0.58731 (4)	0.0490 (3)
C1	0.86862 (11)	0.87814 (19)	0.73528 (6)	0.0455 (4)
C2	0.81042 (12)	0.9977 (2)	0.76159 (6)	0.0511 (4)
H2A	0.7516	1.0388	0.7461	0.061*
C3	0.84119 (13)	1.0540 (2)	0.81085 (6)	0.0544 (4)
C4	0.92785 (14)	0.9988 (2)	0.83548 (6)	0.0575 (4)
H4	0.9470	1.0400	0.8689	0.069*
C5	0.98513 (14)	0.8808 (2)	0.80907 (7)	0.0614 (5)
H5	1.0444	0.8418	0.8246	0.074*
C6	0.95580 (13)	0.8195 (2)	0.75978 (6)	0.0568 (4)
H6	0.9948	0.7379	0.7427	0.068*
C7	0.83918 (12)	0.8096 (2)	0.68307 (6)	0.0486 (4)
H7	0.8713	0.7136	0.6700	0.058*
C8	0.67452 (11)	0.86358 (18)	0.57603 (5)	0.0406 (3)
C9	0.64991 (11)	0.76616 (18)	0.52671 (5)	0.0413 (3)
C10	0.55246 (12)	0.7776 (2)	0.50671 (6)	0.0528 (4)
H10	0.5052	0.8451	0.5241	0.063*
C11	0.52533 (14)	0.6893 (2)	0.46127 (7)	0.0610 (5)
H11	0.4594	0.6969	0.4488	0.073*
C12	0.59315 (13)	0.5906 (2)	0.43399 (6)	0.0540 (4)
C13	0.69117 (13)	0.5831 (2)	0.45316 (6)	0.0547 (4)
H13	0.7389	0.5193	0.4348	0.066*
C14	0.71912 (12)	0.6688 (2)	0.49895 (6)	0.0499 (4)
H14	0.7851	0.6610	0.5113	0.060*
C15	0.56269 (19)	0.4938 (3)	0.38453 (8)	0.0806 (6)
H15A	0.4905	0.4864	0.3829	0.121*
H15B	0.5908	0.3821	0.3860	0.121*
H15C	0.5873	0.5512	0.3532	0.121*
H2	0.7769 (14)	0.6969 (16)	0.6020 (8)	0.080*

	U11	U22	U33	U12	U13	U23
F1	0.1050 (10)	0.0996 (9)	0.0693 (7)	0.0196 (8)	−0.0026 (6)	−0.0352 (7)
N1	0.0550 (8)	0.0461 (7)	0.0383 (6)	−0.0006 (6)	−0.0032 (5)	−0.0095 (6)
N2	0.0587 (8)	0.0447 (7)	0.0404 (7)	0.0068 (6)	−0.0079 (6)	−0.0115 (5)
O1	0.0539 (6)	0.0436 (6)	0.0495 (6)	0.0052 (5)	0.0031 (5)	−0.0070 (5)
C1	0.0524 (8)	0.0445 (8)	0.0398 (8)	−0.0040 (7)	−0.0021 (6)	−0.0010 (6)
C2	0.0546 (9)	0.0536 (9)	0.0452 (9)	0.0010 (7)	−0.0062 (7)	−0.0052 (7)
C3	0.0666 (10)	0.0526 (9)	0.0439 (8)	−0.0038 (8)	0.0036 (7)	−0.0089 (7)
C4	0.0739 (11)	0.0597 (10)	0.0390 (8)	−0.0164 (9)	−0.0092 (8)	0.0003 (7)
C5	0.0638 (10)	0.0673 (11)	0.0532 (9)	−0.0023 (9)	−0.0163 (8)	0.0061 (9)
C6	0.0613 (10)	0.0582 (10)	0.0509 (9)	0.0069 (8)	−0.0062 (8)	−0.0037 (8)
C7	0.0562 (9)	0.0468 (8)	0.0427 (8)	0.0036 (7)	−0.0028 (7)	−0.0070 (7)
C8	0.0447 (8)	0.0385 (7)	0.0385 (7)	−0.0020 (6)	0.0045 (6)	−0.0009 (6)
C9	0.0489 (8)	0.0374 (7)	0.0378 (7)	0.0004 (6)	−0.0020 (6)	0.0013 (6)
C10	0.0514 (9)	0.0525 (9)	0.0545 (9)	0.0080 (7)	−0.0060 (7)	−0.0057 (7)
C11	0.0565 (10)	0.0663 (11)	0.0602 (10)	0.0056 (8)	−0.0186 (8)	−0.0059 (9)
C12	0.0715 (10)	0.0489 (9)	0.0415 (8)	0.0001 (8)	−0.0133 (7)	−0.0010 (7)
C13	0.0673 (10)	0.0565 (10)	0.0402 (8)	0.0120 (8)	−0.0040 (7)	−0.0082 (7)
C14	0.0514 (9)	0.0580 (9)	0.0402 (8)	0.0087 (7)	−0.0062 (6)	−0.0056 (7)
C15	0.1006 (16)	0.0834 (14)	0.0579 (11)	−0.0013 (12)	−0.0259 (11)	−0.0184 (10)

F1—C3	1.352 (2)	C7—H7	0.9300
N1—C7	1.269 (2)	C8—C9	1.487 (2)
N1—N2	1.3841 (16)	C9—C14	1.384 (2)
N2—C8	1.3498 (19)	C9—C10	1.388 (2)
N2—H2	0.902 (9)	C10—C11	1.378 (2)
O1—C8	1.2278 (17)	C10—H10	0.9300
C1—C2	1.386 (2)	C11—C12	1.372 (2)
C1—C6	1.388 (2)	C11—H11	0.9300
C1—C7	1.463 (2)	C12—C13	1.386 (2)
C2—C3	1.368 (2)	C12—C15	1.506 (2)
C2—H2A	0.9300	C13—C14	1.378 (2)
C3—C4	1.374 (3)	C13—H13	0.9300
C4—C5	1.372 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.377 (2)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300
C7—N1—N2	115.30 (13)	O1—C8—C9	121.74 (13)
C8—N2—N1	118.77 (12)	N2—C8—C9	116.10 (12)
C8—N2—H2	124.2 (13)	C14—C9—C10	118.31 (14)
N1—N2—H2	116.6 (13)	C14—C9—C8	123.80 (13)
C2—C1—C6	118.96 (14)	C10—C9—C8	117.87 (13)
C2—C1—C7	121.69 (14)	C11—C10—C9	120.35 (15)
C6—C1—C7	119.33 (14)	C11—C10—H10	119.8
C3—C2—C1	118.74 (15)	C9—C10—H10	119.8
C3—C2—H2A	120.6	C12—C11—C10	121.65 (16)
C1—C2—H2A	120.6	C12—C11—H11	119.2
F1—C3—C2	118.67 (16)	C10—C11—H11	119.2
F1—C3—C4	118.20 (15)	C11—C12—C13	117.91 (15)
C2—C3—C4	123.13 (16)	C11—C12—C15	121.29 (16)
C5—C4—C3	117.72 (15)	C13—C12—C15	120.80 (17)
C5—C4—H4	121.1	C14—C13—C12	121.13 (15)
C3—C4—H4	121.1	C14—C13—H13	119.4
C4—C5—C6	120.76 (16)	C12—C13—H13	119.4
C4—C5—H5	119.6	C13—C14—C9	120.62 (14)
C6—C5—H5	119.6	C13—C14—H14	119.7
C5—C6—C1	120.67 (16)	C9—C14—H14	119.7
C5—C6—H6	119.7	C12—C15—H15A	109.5
C1—C6—H6	119.7	C12—C15—H15B	109.5
N1—C7—C1	121.10 (15)	H15A—C15—H15B	109.5
N1—C7—H7	119.4	C12—C15—H15C	109.5
C1—C7—H7	119.4	H15A—C15—H15C	109.5
O1—C8—N2	122.16 (13)	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (1)	2.04 (1)	2.9322 (17)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.90 (1)	2.04 (1)	2.9322 (17)	169 (2)

Symmetry code: (i) .