N-(4-Fluorobenzoyl)-2-hydroxy-4-methyl­benzohydrazide

Feng, H.-M.; Wang, X.; Lei, K.-W.

doi:10.1107/S1600536808029292

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1953

doi:10.1107/S1600536808029292

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N-(4-Fluorobenzoyl)-2-hydroxy-4-methylbenzohydrazide

Hai-Mei Feng,^a Xin Wang ^b and Ke-Wei Lei ^a ^*

^aState Key Laboratory Base of Novel Functional Materials and Preparation Science, Institute of Solid Materials Chemistry, Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, People's Republic of China, and ^bZhejiang Textile and Fashion College, Ningbo 315211, People's Republic of China
^*Correspondence e-mail: leikeweipublic@hotmail.com

(Received 11 September 2008; accepted 12 September 2008; online 17 September 2008)

In the title compound, C₁₅H₁₃FN₂O₃, the aromatic rings are aligned at an angle of 10.15 (3)°. The molecules are packed with π–π stacking interactions [mean interplanar distances of 3.339 (2) and 3.357 (3) Å] and the crystal structure is stabilized by intermolecular 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_r = 288.27
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.139
S = 1.02
2274 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.45 e Å⁻³

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) -x+2, -y, -z+1; (ii) -x+1, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029292/ng2492sup1.cif

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

checkCIF report

Comment top

The chemistry of salicylic acid has attracted the interest of reseachers since 1860s in the application area of skin science. After a long period, investigations in this area have received a new impulse (Dou et al., 2006) and recently there has been notable progress especially regarding the synthesis of new derivatives. N-acylsalicylhydrazide is one of the important kind, which have been used extensively as ligands in the field of coordination chemistry. Some of the reasons are that the intramolecular hydrogen bond between the O and N atoms plays an important role in the formation of metal complexes, and the N-acylsalicylhydrazide compounds show photoluminescence in the solid state by proton transfer from the O atom to the N atom (Majumder et al., 2006). There several this kind of ligand have been reported, such as N-phenylsalicylhydrazidate (Liu et al., 2001), N-(2-methylpropanoyl)salicylhydrazide (John et al., 2005), N-cyclohexanoylsalicylhydrazidate (John et al., 2006), N-3-phenyl-trans-2-propenoylsalicylhydrazide (Moon et al., 2006) and so on. With the aim of gaining a deeper insight into the structural aspects responsible for the fluorescent properties in the solid state and crystallographic analysis of the title compound (I), has been carried out and the results are presented in this paper.

The molecular structure of (I), C₁₅H₁₃FN₂O₃, is illustrated in Fig. 1. The bond length and bond angle in (I) are within normal ranges. The bond distances between C—O of carbonyl are significantly shorter than C6—O1 bond distances (Table 1). Atom O1, O2, N1 and N2 are nearly coplanar with the plane of benzene rings that contain C2–C7. The O3 atomic deviation is 0.394 (2) Å from the plane of benzene rings that contain C10–C15 and 0.703 (2) Å from the plane of benzene rings that contain C2–C7. The dihedral angel between the two planes of benzene rings is 10.15 (3)°.

The mean interplanar distance of 3.339 (2) Å between the plane of benzene rings that contain C2–C7 and 3.357 (3) Å between the plane of benzene rings that contain C10–C15 respectively suggests that the ligands are engaged in π–π stacking interactions with a offset face-to-face style. The molecular conformation is characterized by an N—H···O and C—H···O hydrogen bonds and the crystal packing is stabilized by N—H···O and O—H···O hydrogen bonds(Fig. 2).

Related literature top

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 top

4-fluorobenzoyl chloride (0.795 g, 5 mmol) and 2-hydroxy-4-methylbenzohydrazide (0.830 g, 5 mmol) were added to 30 ml of DMF solution with an external ice–water bath. When 0.607 g (6 mmol) of triethylamine was added, a white suspension immediately appeared. The suspension was then filtered. The left solution was volume reduced to about one-third on rotary evaporator. After 7 days crystals of the title compound were obtained from the left solution. Yield: 92.2%. Melting point: 217–226 °C. Calcd. for C₁₅H₁₃FN₂O₃: C, 62.50; H, 4.51; N, 9.72; Found: C, 62.24; H, 4.55; N, 9.65%

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view of π–π stacking of (I) and H bonds.

N-(4-Fluorobenzoyl)-2-hydroxy-4-methylbenzohydrazide top

Crystal data top

C₁₅H₁₃FN₂O₃	Z = 2
M_r = 288.27	F(000) = 300
Triclinic, P1	D_x = 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

Data collection top

Bruker Kappa APEXII diffractometer	2090 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 25.0°, θ_min = 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 top

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(F_o²) + (0.093P)² + 0.2642P] where P = (F_o² + 2F_c²)/3
2274 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₅H₁₃FN₂O₃	γ = 105.538 (1)°
M_r = 288.27	V = 652.2 (2) Å³
Triclinic, P1	Z = 2
a = 7.0969 (13) Å	Mo Kα radiation
b = 7.2994 (14) Å	µ = 0.11 mm⁻¹
c = 13.701 (3) Å	T = 296 K
α = 102.854 (2)°	0.54 × 0.30 × 0.25 mm
β = 97.754 (3)°

Data collection top

Bruker Kappa APEXII diffractometer	2090 reflections with I > 2σ(I)
4591 measured reflections	R_int = 0.024
2274 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.02	Δρ_max = 0.39 e Å⁻³
2274 reflections	Δρ_min = −0.45 e Å⁻³
191 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃FN₂O₃
M_r	288.27
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.0969 (13), 7.2994 (14), 13.701 (3)
α, β, γ (°)	102.854 (2), 97.754 (3), 105.538 (1)
V (Å³)	652.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.54 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4591, 2274, 2090
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.139, 1.02
No. of reflections	2274
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.45

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond angles (º) top

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O1	0.8597	1.9148	2.6224 (19)	138.64
O1—H1E···O3ⁱ	0.8202	1.8839	2.7035 (18)	177.34
N2—H2A···O2ⁱⁱ	0.8598	2.1091	2.9079 (19)	154.32

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y+1, −z+1.

Acknowledgements

This project was supported by the Talent Fund of Ningbo University (grant No. 2006668) and sponsored by the K. C. Wong Magna Fund of Ningbo University.

References

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