2-(2-Fluoro-biphenyl-4-yl)-N'-(propan-2-yl-idene)propanohydrazide.

In the title compound, C(18)H(19)FN(2)O, the hydrazide side chain is approximately perpendicular to the central ring [dihedral angle = 76.80 (5)°]. The F atom is disordered over two positions with occupancies of 0.818 (2) and 0.182 (2). The packing consists of chains of mol-ecules parallel to the a axis, connected by a bifurcated N-H⋯(O,N) hydrogen bond and a weak C(phen-yl)-H⋯O hydrogen bond. The packing is extended to a layer structure parallel to the ab plane by a weak C(phen-yl)-H⋯F hydrogen bond.

Related literature

For the biological activity of hydrazides, see: Kumar et al. (2009 ▶); Galal et al.(2009 ▶); Bordoloi et al. (2009 ▶). For their use as inter­mediates in the synthesis of heterocyclic compounds, see: Küçükgüzel et al. (2007 ▶); Navidpour et al. (2006 ▶); Stocks et al. (2004 ▶). For details of the preparation, see: Furniss et al. (1989 ▶).

Experimental

Crystal data

C18H19FN2O

M = 298.35

Orthorhombic,

a = 7.5963 (3) Å

b = 7.3633 (3) Å

c = 27.7430 (11) Å

V = 1551.77 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

33827 measured reflections

2221 independent reflections

2019 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.076

S = 1.00

2221 reflections

210 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009049/bt5206sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009049/bt5206Isup2.hkl

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

C18H19FN2O	Dx = 1.277 Mg m−3
Mr = 298.35	Melting point = 403–405 K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
a = 7.5963 (3) Å	Cell parameters from 14388 reflections
b = 7.3633 (3) Å	θ = 2.7–30.7°
c = 27.7430 (11) Å	µ = 0.09 mm−1
V = 1551.77 (11) Å3	T = 100 K
Z = 4	Block, colourless
F(000) = 632	0.3 × 0.2 × 0.2 mm

Oxford Diffraction Xcalibur E diffractometer	2019 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.033
graphite	θmax = 29.6°, θmin = 2.8°
Detector resolution: 16.1419 pixels mm-1	h = −10→10
ω scan	k = −10→10
33827 measured reflections	l = −37→38
2221 independent 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.054P)2] where P = (Fo2 + 2Fc2)/3
2221 reflections	(Δ/σ)max = 0.004
210 parameters	Δρmax = 0.26 e Å−3
2 restraints	Δρmin = −0.17 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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)6.3713 (0.0030) x + 4.0007 (0.0044) y - 1.0030 (0.0204) z = 5.8734 (0.0077)* -0.0031 (0.0011) C7 * 0.0023 (0.0012) C8 * 0.0002 (0.0014) C9 * -0.0018 (0.0013) C10 * 0.0009 (0.0012) C11 * 0.0016 (0.0012) C12Rms deviation of fitted atoms = 0.0019- 6.9258 (0.0030) x + 0.8494 (0.0036) y + 10.9376 (0.0231) z = 0.9826 (0.0143)Angle to previous plane (with approximate esd) = 44.25 ( 0.05 )* -0.0036 (0.0011) C1 * 0.0203 (0.0014) C2 * 0.0261 (0.0012) C3 * -0.0276 (0.0010) F_a * 0.0066 (0.0017) C4 * -0.0181 (0.0021) C5 * 0.0140 (0.0023) F'_b * -0.0177 (0.0014) C6Rms deviation of fitted atoms = 0.01863.4515 (0.0049) x - 4.4863 (0.0030) y + 18.0294 (0.0071) z = 11.4681 (0.0049)Angle to previous plane (with approximate esd) = 76.80 ( 0.05 )* -0.0272 (0.0009) C13 * 0.0140 (0.0012) C15 * -0.0802 (0.0013) C16 * -0.0112 (0.0011) C17 * 0.1063 (0.0013) N1 * 0.0372 (0.0012) N2 * -0.0387 (0.0006) ORms deviation of fitted atoms = 0.0557

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	Occ. (<1)
C1	0.72830 (18)	0.4169 (2)	0.51831 (5)	0.0147 (3)
C2	0.7404 (2)	0.6049 (2)	0.51357 (5)	0.0174 (3)
H2	0.7876	0.6764	0.5390	0.021*
C3	0.68322 (19)	0.6863 (2)	0.47155 (5)	0.0176 (3)
H3	0.6923	0.8146	0.4690	0.021*	0.182 (2)
F	0.70634 (17)	0.86695 (15)	0.46725 (4)	0.0264 (3)	0.818 (2)
C4	0.61277 (19)	0.5909 (2)	0.43257 (5)	0.0161 (3)
C5	0.60263 (19)	0.4025 (2)	0.43852 (5)	0.0174 (3)
H5	0.5562	0.3308	0.4131	0.021*	0.818 (2)
F'	0.5315 (7)	0.3049 (7)	0.40400 (17)	0.021*	0.182 (2)
C6	0.65842 (18)	0.31696 (19)	0.48053 (6)	0.0166 (3)
H6	0.6485	0.1888	0.4834	0.020*
C7	0.55385 (19)	0.6825 (2)	0.38780 (6)	0.0185 (3)
C8	0.5944 (2)	0.6080 (2)	0.34264 (6)	0.0270 (3)
H8	0.6626	0.5001	0.3406	0.032*
C9	0.5349 (3)	0.6917 (3)	0.30082 (7)	0.0377 (5)
H9	0.5624	0.6403	0.2703	0.045*
C10	0.4364 (3)	0.8486 (3)	0.30319 (7)	0.0382 (5)
H10	0.3962	0.9046	0.2744	0.046*
C11	0.3960 (2)	0.9247 (3)	0.34731 (7)	0.0331 (4)
H11	0.3284	1.0331	0.3489	0.040*
C12	0.4548 (2)	0.8419 (2)	0.38960 (6)	0.0248 (3)
H12	0.4270	0.8946	0.4199	0.030*
C13	0.79126 (17)	0.33065 (19)	0.56537 (5)	0.0148 (3)
H13	0.9016	0.3937	0.5757	0.018*
C14	0.8295 (2)	0.1268 (2)	0.56215 (6)	0.0204 (3)
H14A	0.7195	0.0609	0.5562	0.031*
H14B	0.8814	0.0850	0.5925	0.031*
H14C	0.9120	0.1039	0.5357	0.031*
C15	0.64955 (18)	0.36582 (19)	0.60353 (5)	0.0145 (3)
C16	0.5793 (2)	0.6916 (2)	0.69282 (6)	0.0204 (3)
C17	0.4463 (2)	0.7287 (3)	0.73133 (7)	0.0292 (4)
H17A	0.3519	0.6382	0.7295	0.044*
H17B	0.3967	0.8503	0.7267	0.044*
H17C	0.5031	0.7218	0.7630	0.044*
C18	0.7172 (3)	0.8334 (3)	0.68449 (8)	0.0398 (5)
H18A	0.7886	0.7998	0.6565	0.060*	0.50
H18B	0.7928	0.8426	0.7130	0.060*	0.50
H18C	0.6604	0.9508	0.6786	0.060*	0.50
H18D	0.7059	0.9290	0.7089	0.060*	0.50
H18E	0.7017	0.8862	0.6523	0.060*	0.50
H18F	0.8341	0.7779	0.6868	0.060*	0.50
O	0.51235 (13)	0.27749 (14)	0.60489 (4)	0.0192 (2)
N1	0.56165 (16)	0.54268 (18)	0.66949 (5)	0.0185 (3)
N2	0.68360 (16)	0.50682 (18)	0.63339 (5)	0.0169 (3)
H01	0.785 (3)	0.562 (3)	0.6336 (8)	0.036 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0117 (6)	0.0169 (7)	0.0155 (7)	0.0008 (5)	0.0022 (5)	0.0009 (5)
C2	0.0180 (6)	0.0160 (7)	0.0182 (7)	−0.0017 (5)	0.0010 (5)	−0.0020 (5)
C3	0.0208 (6)	0.0132 (6)	0.0188 (7)	−0.0002 (5)	0.0030 (6)	0.0013 (6)
F	0.0436 (7)	0.0107 (5)	0.0249 (6)	−0.0022 (5)	−0.0030 (5)	0.0015 (4)
C4	0.0143 (6)	0.0174 (7)	0.0167 (7)	0.0012 (5)	0.0024 (5)	0.0000 (5)
C5	0.0167 (6)	0.0175 (7)	0.0180 (7)	−0.0011 (5)	−0.0003 (5)	−0.0024 (6)
C6	0.0173 (6)	0.0130 (6)	0.0195 (7)	0.0004 (5)	0.0012 (5)	−0.0010 (5)
C7	0.0172 (6)	0.0192 (7)	0.0192 (7)	−0.0033 (5)	−0.0012 (5)	0.0038 (6)
C8	0.0348 (9)	0.0253 (8)	0.0210 (8)	−0.0040 (7)	0.0003 (7)	0.0008 (7)
C9	0.0572 (12)	0.0355 (11)	0.0204 (8)	−0.0150 (9)	−0.0073 (8)	0.0029 (8)
C10	0.0443 (11)	0.0380 (10)	0.0324 (10)	−0.0160 (9)	−0.0173 (9)	0.0178 (9)
C11	0.0237 (8)	0.0333 (9)	0.0424 (11)	−0.0010 (7)	−0.0048 (8)	0.0176 (9)
C12	0.0212 (7)	0.0260 (8)	0.0273 (8)	0.0019 (6)	0.0020 (6)	0.0065 (7)
C13	0.0122 (6)	0.0156 (6)	0.0168 (7)	0.0001 (5)	0.0000 (5)	−0.0002 (5)
C14	0.0212 (7)	0.0167 (7)	0.0231 (8)	0.0042 (5)	0.0008 (6)	0.0007 (6)
C15	0.0139 (6)	0.0148 (6)	0.0147 (6)	0.0023 (5)	−0.0020 (5)	0.0019 (5)
C16	0.0188 (7)	0.0219 (7)	0.0206 (8)	0.0015 (6)	0.0003 (6)	−0.0009 (6)
C17	0.0313 (9)	0.0259 (8)	0.0303 (9)	0.0017 (7)	0.0109 (7)	−0.0046 (7)
C18	0.0399 (11)	0.0302 (9)	0.0492 (12)	−0.0126 (8)	0.0197 (9)	−0.0177 (9)
O	0.0148 (5)	0.0201 (5)	0.0226 (5)	−0.0028 (4)	0.0010 (4)	−0.0004 (5)
N1	0.0138 (5)	0.0228 (6)	0.0190 (6)	0.0019 (5)	0.0016 (5)	−0.0025 (5)
N2	0.0111 (5)	0.0207 (6)	0.0190 (6)	−0.0006 (5)	0.0004 (5)	−0.0036 (5)

C1—C6	1.386 (2)	C2—H2	0.9500
C1—C2	1.394 (2)	C3—H3	0.9500
C1—C13	1.529 (2)	C5—H5	0.9500
C2—C3	1.381 (2)	C6—H6	0.9500
C3—F	1.3472 (18)	C8—H8	0.9500
C3—C4	1.396 (2)	C9—H9	0.9500
C4—C5	1.399 (2)	C10—H10	0.9500
C4—C7	1.482 (2)	C11—H11	0.9500
C5—F'	1.314 (5)	C12—H12	0.9500
C5—C6	1.391 (2)	C13—H13	1.0000
C7—C12	1.395 (2)	C14—H14A	0.9800
C7—C8	1.402 (2)	C14—H14B	0.9800
C8—C9	1.389 (3)	C14—H14C	0.9800
C9—C10	1.378 (3)	C17—H17A	0.9800
C10—C11	1.381 (3)	C17—H17B	0.9800
C11—C12	1.395 (2)	C17—H17C	0.9800
C13—C14	1.532 (2)	C18—H18A	0.9800
C13—C15	1.532 (2)	C18—H18B	0.9800
C15—O	1.2291 (17)	C18—H18C	0.9800
C15—N2	1.3530 (19)	C18—H18D	0.9800
C16—N1	1.280 (2)	C18—H18E	0.9800
C16—C17	1.495 (2)	C18—H18F	0.9800
C16—C18	1.497 (2)	N2—H01	0.87 (3)
N1—N2	1.3896 (17)
C6—C1—C2	118.77 (13)	C9—C10—H10	119.9
C6—C1—C13	123.03 (13)	C11—C10—H10	119.9
C2—C1—C13	118.19 (12)	C10—C11—H11	120.1
C3—C2—C1	119.32 (13)	C12—C11—H11	120.1
F—C3—C2	117.53 (14)	C7—C12—H12	119.7
F—C3—C4	118.55 (14)	C11—C12—H12	119.7
C2—C3—C4	123.81 (14)	C1—C13—H13	108.2
C3—C4—C5	115.37 (13)	C14—C13—H13	108.2
C3—C4—C7	122.42 (13)	C15—C13—H13	108.2
C5—C4—C7	122.22 (13)	C13—C14—H14A	109.5
F'—C5—C6	119.2 (3)	C13—C14—H14B	109.5
F'—C5—C4	118.6 (3)	H14A—C14—H14B	109.5
C6—C5—C4	122.08 (13)	C13—C14—H14C	109.5
C1—C6—C5	120.65 (13)	H14A—C14—H14C	109.5
C12—C7—C8	118.66 (14)	H14B—C14—H14C	109.5
C12—C7—C4	121.03 (14)	C16—C17—H17A	109.5
C8—C7—C4	120.30 (14)	C16—C17—H17B	109.5
C9—C8—C7	120.09 (17)	H17A—C17—H17B	109.5
C10—C9—C8	120.58 (18)	C16—C17—H17C	109.5
C9—C10—C11	120.20 (17)	H17A—C17—H17C	109.5
C10—C11—C12	119.82 (17)	H17B—C17—H17C	109.5
C7—C12—C11	120.65 (16)	C16—C18—H18A	109.5
C1—C13—C14	114.63 (12)	C16—C18—H18B	109.5
C1—C13—C15	107.47 (11)	H18A—C18—H18B	109.5
C14—C13—C15	109.83 (12)	C16—C18—H18C	109.5
O—C15—N2	123.32 (14)	H18A—C18—H18C	109.5
O—C15—C13	121.84 (13)	H18B—C18—H18C	109.5
N2—C15—C13	114.74 (12)	C16—C18—H18D	109.5
N1—C16—C17	116.55 (14)	H18A—C18—H18D	141.1
N1—C16—C18	126.34 (15)	H18B—C18—H18D	56.3
C17—C16—C18	117.10 (15)	H18C—C18—H18D	56.3
C16—N1—N2	117.22 (13)	C16—C18—H18E	109.5
C15—N2—N1	117.36 (12)	H18A—C18—H18E	56.3
C3—C2—H2	120.3	H18B—C18—H18E	141.1
C1—C2—H2	120.3	H18C—C18—H18E	56.3
C2—C3—H3	118.1	H18D—C18—H18E	109.5
C4—C3—H3	118.1	C16—C18—H18F	109.5
C6—C5—H5	119.0	H18A—C18—H18F	56.3
C4—C5—H5	119.0	H18B—C18—H18F	56.3
C1—C6—H6	119.7	H18C—C18—H18F	141.1
C5—C6—H6	119.7	H18D—C18—H18F	109.5
C9—C8—H8	120.0	H18E—C18—H18F	109.5
C7—C8—H8	120.0	C15—N2—H01	122.2 (15)
C10—C9—H9	119.7	N1—N2—H01	119.6 (15)
C8—C9—H9	119.7
C6—C1—C2—C3	−0.1 (2)	C4—C7—C8—C9	178.30 (16)
C13—C1—C2—C3	−179.52 (13)	C7—C8—C9—C10	0.3 (3)
C1—C2—C3—F	−176.31 (14)	C8—C9—C10—C11	0.1 (3)
C1—C2—C3—C4	−0.1 (2)	C9—C10—C11—C12	−0.2 (3)
F—C3—C4—C5	176.22 (13)	C8—C7—C12—C11	0.5 (2)
C2—C3—C4—C5	0.1 (2)	C4—C7—C12—C11	−178.35 (14)
F—C3—C4—C7	−3.4 (2)	C10—C11—C12—C7	−0.1 (3)
C2—C3—C4—C7	−179.51 (14)	C6—C1—C13—C14	19.40 (19)
C3—C4—C5—F'	177.4 (3)	C2—C1—C13—C14	−161.26 (13)
C7—C4—C5—F'	−3.0 (3)	C6—C1—C13—C15	−102.98 (15)
C3—C4—C5—C6	0.3 (2)	C2—C1—C13—C15	76.36 (16)
C7—C4—C5—C6	179.84 (13)	C1—C13—C15—O	77.34 (16)
C2—C1—C6—C5	0.5 (2)	C14—C13—C15—O	−47.97 (18)
C13—C1—C6—C5	179.81 (13)	C1—C13—C15—N2	−99.18 (14)
F'—C5—C6—C1	−177.7 (3)	C14—C13—C15—N2	135.52 (13)
C4—C5—C6—C1	−0.5 (2)	C17—C16—N1—N2	179.62 (13)
C3—C4—C7—C12	−44.0 (2)	C18—C16—N1—N2	1.1 (2)
C5—C4—C7—C12	136.45 (16)	O—C15—N2—N1	5.0 (2)
C3—C4—C7—C8	137.17 (16)	C13—C15—N2—N1	−178.54 (12)
C5—C4—C7—C8	−42.4 (2)	C16—N1—N2—C15	−169.44 (14)
C12—C7—C8—C9	−0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H01···Oi	0.87 (3)	2.24 (3)	3.0633 (17)	158 (2)
N2—H01···N1i	0.87 (3)	2.45 (2)	3.0632 (17)	127.7 (19)
C6—H6···Fii	0.95	2.45	3.3537 (18)	159
C2—H2···Oi	0.95	2.52	3.3816 (19)	150
C18—H18A···Oi	0.98	2.29	3.251 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H01⋯Oi	0.87 (3)	2.24 (3)	3.0633 (17)	158 (2)
N2—H01⋯N1i	0.87 (3)	2.45 (2)	3.0632 (17)	127.7 (19)
C6—H6⋯Fii	0.95	2.45	3.3537 (18)	159
C2—H2⋯Oi	0.95	2.52	3.3816 (19)	150
C18—H18A⋯Oi	0.98	2.29	3.251 (2)	166

Symmetry codes: (i) ; (ii) .