N-(4-Fluorobenzoyl)-2-hydroxy-4-methyl-benzohydrazide.

In the title compound, C(15)H(13)FN(2)O(3), the aromatic rings are aligned at an angle of 10.15 (3)°. The mol-ecules are packed with π-π stacking inter-actions [mean inter-planar distances of 3.339 (2) and 3.357 (3) Å] and the crystal structure is stabilized by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds. An intramolecular N-H⋯O interaction also occurs.

Related literature

For background on the chemistry of salicylic acid, see: Dou et al. (2006 ▶). For related compounds, see: John et al. (2005 ▶, 2006 ▶); Liu et al. (2001 ▶); Majumder et al. (2006 ▶); Moon et al. (2006 ▶).

Experimental

Crystal data

C15H13FN2O3

M = 288.27

Triclinic,

a = 7.0969 (13) Å

b = 7.2994 (14) Å

c = 13.701 (3) Å

α = 102.854 (2)°

β = 97.754 (3)°

γ = 105.538 (1)°

V = 652.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 (2) K

0.54 × 0.30 × 0.25 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: none

4591 measured reflections

2274 independent reflections

2090 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.139

S = 1.02

2274 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (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 datablocks global, I. DOI: 10.1107/S1600536808029292/ng2492sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029292/ng2492Isup2.hkl

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

C15H13FN2O3	Z = 2
Mr = 288.27	F(000) = 300
Triclinic, P1	Dx = 1.468 Mg m−3
Hall symbol: -P 1	Melting point = 490–499 K
a = 7.0969 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.2994 (14) Å	Cell parameters from 6530 reflections
c = 13.701 (3) Å	θ = 1.6–27.6°
α = 102.854 (2)°	µ = 0.11 mm−1
β = 97.754 (3)°	T = 296 K
γ = 105.538 (1)°	Block, colourless
V = 652.2 (2) Å3	0.54 × 0.30 × 0.25 mm

Bruker Kappa APEXII diffractometer	2090 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 25.0°, θmin = 1.6°
Detector resolution: 0 pixels mm-1	h = −8→8
ω scans	k = −8→8
4591 measured reflections	l = −16→16
2274 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.093P)2 + 0.2642P] where P = (Fo2 + 2Fc2)/3
2274 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.45 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	1.5146 (3)	0.7327 (3)	0.90895 (14)	0.0382 (4)
H1A	1.5688	0.6263	0.9116	0.057*
H1B	1.4846	0.7824	0.9741	0.057*
H1C	1.6105	0.8366	0.8931	0.057*
C2	1.3255 (2)	0.6585 (2)	0.82719 (12)	0.0275 (4)
C3	1.1619 (2)	0.7274 (2)	0.83934 (12)	0.0291 (4)
H3A	1.1679	0.8211	0.8990	0.035*
C4	0.9911 (2)	0.6566 (2)	0.76276 (12)	0.0256 (4)
H4A	0.8839	0.7043	0.7722	0.031*
C5	1.3107 (2)	0.5166 (2)	0.73751 (12)	0.0260 (4)
H5A	1.4184	0.4696	0.7285	0.031*
C6	1.1384 (2)	0.4435 (2)	0.66103 (11)	0.0227 (3)
C7	0.9748 (2)	0.5153 (2)	0.67156 (11)	0.0215 (3)
C8	0.7818 (2)	0.4502 (2)	0.59554 (11)	0.0210 (3)
C9	0.5611 (2)	0.0444 (2)	0.37524 (11)	0.0225 (3)
C10	0.3744 (2)	−0.0450 (2)	0.29516 (12)	0.0228 (4)
C11	0.3805 (2)	−0.1729 (2)	0.20387 (12)	0.0292 (4)
H11A	0.4995	−0.1983	0.1948	0.035*
C12	0.1944 (2)	−0.0106 (2)	0.30968 (12)	0.0258 (4)
H12A	0.1892	0.0725	0.3708	0.031*
C13	0.0234 (2)	−0.1002 (2)	0.23314 (13)	0.0298 (4)
H13A	−0.0972	−0.0786	0.2422	0.036*
C14	0.2107 (3)	−0.2622 (3)	0.12657 (13)	0.0332 (4)
H14A	0.2140	−0.3465	0.0654	0.040*
C15	0.0363 (2)	−0.2216 (2)	0.14356 (13)	0.0311 (4)
F	−0.13083 (16)	−0.30700 (16)	0.06798 (8)	0.0459 (3)
N1	0.76066 (18)	0.30055 (19)	0.51310 (10)	0.0239 (3)
H1D	0.8590	0.2550	0.5049	0.029*
N2	0.58263 (18)	0.21862 (18)	0.44102 (9)	0.0223 (3)
H2A	0.4916	0.2760	0.4386	0.027*
O1	1.12712 (16)	0.30064 (17)	0.57426 (8)	0.0287 (3)
H1E	1.1820	0.2223	0.5895	0.043*
O2	0.64816 (15)	0.52694 (16)	0.60736 (8)	0.0270 (3)
O3	0.69450 (16)	−0.03614 (17)	0.38199 (9)	0.0320 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0302 (9)	0.0413 (10)	0.0360 (9)	0.0091 (8)	−0.0048 (7)	0.0057 (8)
C2	0.0260 (8)	0.0262 (8)	0.0273 (8)	0.0051 (6)	−0.0005 (6)	0.0084 (6)
C3	0.0343 (9)	0.0250 (8)	0.0252 (8)	0.0118 (7)	0.0003 (7)	0.0014 (6)
C4	0.0285 (8)	0.0245 (8)	0.0259 (8)	0.0134 (6)	0.0045 (6)	0.0056 (6)
C5	0.0204 (8)	0.0303 (8)	0.0308 (8)	0.0111 (6)	0.0054 (6)	0.0111 (7)
C6	0.0243 (7)	0.0233 (7)	0.0228 (7)	0.0099 (6)	0.0049 (6)	0.0074 (6)
C7	0.0222 (8)	0.0202 (7)	0.0231 (8)	0.0085 (6)	0.0026 (6)	0.0071 (6)
C8	0.0217 (7)	0.0220 (7)	0.0225 (7)	0.0102 (6)	0.0052 (6)	0.0079 (6)
C9	0.0229 (8)	0.0233 (8)	0.0244 (7)	0.0119 (6)	0.0056 (6)	0.0064 (6)
C10	0.0231 (8)	0.0194 (7)	0.0251 (8)	0.0068 (6)	0.0023 (6)	0.0057 (6)
C11	0.0261 (8)	0.0307 (9)	0.0293 (8)	0.0102 (7)	0.0042 (6)	0.0043 (7)
C12	0.0263 (8)	0.0201 (7)	0.0310 (8)	0.0089 (6)	0.0043 (6)	0.0056 (6)
C13	0.0226 (8)	0.0249 (8)	0.0417 (9)	0.0074 (6)	0.0017 (7)	0.0114 (7)
C14	0.0371 (9)	0.0316 (9)	0.0244 (8)	0.0078 (7)	0.0009 (7)	0.0015 (7)
C15	0.0273 (8)	0.0267 (8)	0.0333 (9)	0.0027 (6)	−0.0064 (7)	0.0107 (7)
F	0.0361 (6)	0.0447 (7)	0.0410 (6)	0.0040 (5)	−0.0165 (5)	0.0046 (5)
N1	0.0192 (6)	0.0269 (7)	0.0242 (7)	0.0128 (5)	−0.0015 (5)	0.0011 (5)
N2	0.0184 (6)	0.0238 (7)	0.0241 (6)	0.0112 (5)	−0.0011 (5)	0.0024 (5)
O1	0.0284 (6)	0.0353 (6)	0.0252 (6)	0.0208 (5)	0.0023 (4)	0.0026 (5)
O2	0.0255 (6)	0.0305 (6)	0.0271 (6)	0.0171 (5)	0.0025 (4)	0.0032 (5)
O3	0.0293 (6)	0.0300 (6)	0.0353 (6)	0.0180 (5)	−0.0014 (5)	0.0004 (5)

C1—C2	1.511 (2)	C9—N2	1.342 (2)
C1—H1A	0.9601	C9—C10	1.487 (2)
C1—H1B	0.9601	C10—C12	1.397 (2)
C1—H1C	0.9601	C10—C11	1.398 (2)
C2—C5	1.390 (2)	C11—C14	1.388 (2)
C2—C3	1.399 (2)	C11—H11A	0.9300
C3—C4	1.385 (2)	C12—C13	1.388 (2)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C7	1.401 (2)	C13—C15	1.375 (3)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.391 (2)	C14—C15	1.385 (3)
C5—H5A	0.9300	C14—H14A	0.9300
C6—O1	1.3732 (19)	C15—F	1.3614 (18)
C6—C7	1.407 (2)	N1—N2	1.3875 (17)
C7—C8	1.494 (2)	N1—H1D	0.8600
C8—O2	1.2351 (18)	N2—H2A	0.8600
C8—N1	1.345 (2)	O1—H1E	0.8200
C9—O3	1.2451 (19)
C2—C1—H1A	109.5	O3—C9—C10	122.26 (13)
C2—C1—H1B	109.5	N2—C9—C10	117.42 (12)
H1A—C1—H1B	109.5	C12—C10—C11	119.65 (14)
C2—C1—H1C	109.5	C12—C10—C9	122.36 (14)
H1A—C1—H1C	109.5	C11—C10—C9	117.95 (13)
H1B—C1—H1C	109.5	C14—C11—C10	120.64 (15)
C5—C2—C3	118.40 (14)	C14—C11—H11A	119.7
C5—C2—C1	119.88 (15)	C10—C11—H11A	119.7
C3—C2—C1	121.71 (15)	C13—C12—C10	120.17 (15)
C4—C3—C2	120.21 (14)	C13—C12—H12A	119.9
C4—C3—H3A	119.9	C10—C12—H12A	119.9
C2—C3—H3A	119.9	C15—C13—C12	118.47 (15)
C3—C4—C7	122.03 (14)	C15—C13—H13A	120.8
C3—C4—H4A	119.0	C12—C13—H13A	120.8
C7—C4—H4A	119.0	C15—C14—C11	117.78 (15)
C2—C5—C6	121.48 (14)	C15—C14—H14A	121.1
C2—C5—H5A	119.3	C11—C14—H14A	121.1
C6—C5—H5A	119.3	F—C15—C13	118.40 (15)
O1—C6—C5	120.01 (13)	F—C15—C14	118.34 (15)
O1—C6—C7	119.48 (13)	C13—C15—C14	123.26 (15)
C5—C6—C7	120.50 (14)	C8—N1—N2	121.02 (12)
C4—C7—C6	117.33 (14)	C8—N1—H1D	119.5
C4—C7—C8	116.67 (13)	N2—N1—H1D	119.5
C6—C7—C8	125.97 (14)	C9—N2—N1	115.98 (12)
O2—C8—N1	121.54 (13)	C9—N2—H2A	122.0
O2—C8—C7	122.52 (13)	N1—N2—H2A	122.0
N1—C8—C7	115.94 (12)	C6—O1—H1E	109.5
O3—C9—N2	120.31 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O1	0.86	1.92	2.6224 (19)	139.
O1—H1E···O3i	0.82	1.88	2.7035 (18)	177.
N2—H2A···O2ii	0.86	2.11	2.9079 (19)	154.
C4—H4A···O2	0.93	2.47	2.797 (2)	101.

Table 1

Selected bond angles (°)

O1—C6—C5	120.01 (13)
O1—C6—C7	119.48 (13)
O2—C8—N1	121.54 (13)
O2—C8—C7	122.52 (13)
N1—C8—C7	115.94 (12)
O3—C9—N2	120.31 (14)
O3—C9—C10	122.26 (13)
N2—C9—C10	117.42 (12)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O1	0.86	1.92	2.6224 (19)	139
O1—H1E⋯O3i	0.82	1.88	2.7035 (18)	177
N2—H2A⋯O2ii	0.86	2.11	2.9079 (19)	154

Symmetry codes: (i) ; (ii) .