N′-Cyclo­hexyl­idene-2-hydroxy­benzo­hydrazide

Liu, D.

doi:10.1107/S1600536809007636

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o691

doi:10.1107/S1600536809007636

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N′-Cyclohexylidene-2-hydroxybenzohydrazide

Deyun Liu ^a ^*

^aLiaocheng Vocational and Technical College, Liaocheng, 252059, People's Republic of China
^*Correspondence e-mail: lcldy@163.com

(Received 15 February 2009; accepted 2 March 2009; online 6 March 2009)

In the title molecule, C₁₃H₁₆N₂O₂, the cyclohexylidene ring adopts a chair conformation. The intramolecular N—H⋯O hydrogen bond influences the molecular conformation: the benzene ring and the mean plane of the central C(O)NHN fragment form a dihedral angle of 4.9 (1) Å. In the crystal, intermolecular O—H⋯O hydrogen bonds link the molecules into chains propagated along [001].

Related literature

For properties of Shiff-base derivatives, see Sreeja et al. (2003 ). For a related structure, see Luo et al. (2007 ).

Experimental

Crystal data

C₁₃H₁₆N₂O₂
M_r = 232.28
Monoclinic, C c
a = 18.376 (2) Å
b = 5.3386 (10) Å
c = 12.9435 (15) Å
β = 102.241 (2)°
V = 1240.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.39 × 0.29 × 0.27 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.968, T_max = 0.977
2969 measured reflections
1090 independent reflections
898 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.138
S = 1.08
1090 reflections
154 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.97	2.655 (4)	136
O2—H2⋯O1ⁱ	0.82	2.15	2.704 (4)	125
Symmetry code: (i) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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 I, global. DOI: 10.1107/S1600536809007636/cv2521sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007636/cv2521Isup2.hkl

checkCIF report

Comment top

Chemistry of Schiff bases has been intensively investigated in recent years, owing to their coordination properties and diverse applications. Schiff base derivatives and their complexes have been studied for their antifungal and antibacterial activ- ity, and as antiviral drugs (Sreeja et al., 2003). In this paper, we present the crystal structure of the title compound, (I), which was synthesized by the reaction of cyclohexanone and salicyloyl hydrazide.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the compound reported by Luo et al. (2007). The cyclohexylidene ring adopts a chair conformation. Intramolecular N—H···O hydrogen bond (Table 1) influences the molecular conformationthe - dihedral angle between the benzene ring and the plane C1/N1/N2 is 4.9 (1) Å. The plane C1/N1/N2 and ring C8-C13 form a dihedral angle of 37.7 (3) Å. Intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into chains propagated in direction [001].

Related literature top

For properties of Shiff-base derivatives, see Sreeja et al. (2003). For the crystal structure of related compound, see Luo et al. (2007).

Experimental top

Salicyloyl hydrazide (5 mmol) and cyclohexanone (5 mmol),20 ml e nthanol were mixed in 50 ml flash. After stirring 30 min at 353 K, the mixture then cooling slowly to room temperature and affording the title compound, then recrystallized from ethanol, affording the title compound as a red crystalline solid. Elemental analysis: calculated for C₁₃H₁₆N₂O₂: C 67.22, H 6.94, N 12.06%; found: C 67.29, H 6.85, N 12.24%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 molecular structure of (I) with the atomic numbering scheme and 30% probability displacement ellipsoids.

(I) top

Crystal data top

C₁₃H₁₆N₂O₂	F(000) = 496
M_r = 232.28	D_x = 1.243 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 18.376 (2) Å	Cell parameters from 1322 reflections
b = 5.3386 (10) Å	θ = 3.2–27.5°
c = 12.9435 (15) Å	µ = 0.09 mm⁻¹
β = 102.241 (2)°	T = 293 K
V = 1240.9 (3) Å³	Block, red
Z = 4	0.39 × 0.29 × 0.27 mm

Data collection top

Bruker SMART Apex CCD area-detector diffractometer	1090 independent reflections
Radiation source: fine-focus sealed tube	898 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→11
T_min = 0.968, T_max = 0.977	k = −6→6
2969 measured reflections	l = −15→15

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) = 0.138	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0866P)² + 0.3353P] where P = (F_o² + 2F_c²)/3
1090 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.28 e Å⁻³
2 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₃H₁₆N₂O₂	V = 1240.9 (3) Å³
M_r = 232.28	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 18.376 (2) Å	µ = 0.09 mm⁻¹
b = 5.3386 (10) Å	T = 293 K
c = 12.9435 (15) Å	0.39 × 0.29 × 0.27 mm
β = 102.241 (2)°

Data collection top

Bruker SMART Apex CCD area-detector diffractometer	1090 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	898 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.977	R_int = 0.024
2969 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.08	Δρ_max = 0.28 e Å⁻³
1090 reflections	Δρ_min = −0.15 e Å⁻³
154 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
N1	0.18964 (17)	0.6052 (6)	0.1521 (2)	0.0432 (8)
H1	0.1776	0.6179	0.2126	0.052*
N2	0.15740 (18)	0.7600 (7)	0.0684 (2)	0.0475 (8)
O1	0.2584 (2)	0.4124 (5)	0.0501 (2)	0.0577 (8)
O2	0.20359 (16)	0.4399 (5)	0.3488 (2)	0.0511 (8)
H2	0.1965	0.4152	0.4084	0.077*
C1	0.24015 (19)	0.4354 (7)	0.1362 (2)	0.0371 (8)
C2	0.27283 (19)	0.2675 (7)	0.2264 (3)	0.0369 (8)
C3	0.25343 (18)	0.2669 (6)	0.3267 (3)	0.0370 (8)
C4	0.2836 (2)	0.0878 (7)	0.4024 (3)	0.0465 (10)
H4	0.2699	0.0859	0.4675	0.056*
C5	0.3333 (2)	−0.0845 (8)	0.3810 (3)	0.0524 (11)
H5	0.3533	−0.2032	0.4317	0.063*
C6	0.3545 (2)	−0.0838 (7)	0.2838 (3)	0.0505 (11)
H6	0.3890	−0.1997	0.2699	0.061*
C7	0.3240 (2)	0.0891 (7)	0.2088 (3)	0.0422 (9)
H7	0.3380	0.0871	0.1439	0.051*
C8	0.1097 (3)	0.9202 (8)	0.0854 (3)	0.0531 (11)
C9	0.0802 (3)	0.9560 (10)	0.1848 (4)	0.0681 (13)
H9A	0.0993	0.8241	0.2348	0.082*
H9B	0.0976	1.1151	0.2170	0.082*
C10	−0.0029 (3)	0.9511 (13)	0.1616 (5)	0.0863 (18)
H10A	−0.0200	0.9941	0.2253	0.104*
H10B	−0.0198	0.7824	0.1415	0.104*
C11	−0.0380 (3)	1.1323 (12)	0.0730 (5)	0.0874 (17)
H11A	−0.0917	1.1123	0.0572	0.105*
H11B	−0.0266	1.3034	0.0961	0.105*
C12	−0.0081 (3)	1.0816 (13)	−0.0264 (5)	0.0849 (17)
H12A	−0.0253	0.9184	−0.0543	0.102*
H12B	−0.0280	1.2059	−0.0795	0.102*
C13	0.0746 (3)	1.0884 (9)	−0.0060 (4)	0.0690 (14)
H13A	0.0914	1.2591	0.0096	0.083*
H13B	0.0908	1.0354	−0.0691	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0527 (19)	0.059 (2)	0.0189 (15)	0.0072 (17)	0.0087 (13)	0.0043 (13)
N2	0.0493 (18)	0.067 (2)	0.0256 (16)	0.0066 (17)	0.0075 (13)	0.0104 (14)
O1	0.082 (2)	0.0684 (18)	0.0267 (14)	0.0165 (16)	0.0210 (13)	0.0059 (12)
O2	0.0656 (18)	0.0681 (18)	0.0219 (13)	0.0188 (15)	0.0142 (12)	0.0037 (12)
C1	0.044 (2)	0.046 (2)	0.0212 (19)	−0.0032 (16)	0.0065 (15)	−0.0014 (14)
C2	0.0394 (19)	0.046 (2)	0.0239 (18)	−0.0062 (16)	0.0031 (14)	−0.0038 (14)
C3	0.0407 (19)	0.0477 (19)	0.0219 (17)	−0.0004 (18)	0.0048 (14)	−0.0020 (15)
C4	0.052 (2)	0.059 (2)	0.029 (2)	0.004 (2)	0.0115 (17)	0.0057 (17)
C5	0.056 (3)	0.056 (2)	0.043 (3)	0.008 (2)	0.0052 (19)	0.0111 (18)
C6	0.052 (2)	0.055 (2)	0.045 (3)	0.0075 (19)	0.014 (2)	−0.0001 (18)
C7	0.048 (2)	0.051 (2)	0.0291 (19)	0.0004 (18)	0.0118 (16)	−0.0045 (16)
C8	0.053 (2)	0.073 (3)	0.033 (2)	0.002 (2)	0.0079 (18)	0.0075 (19)
C9	0.075 (3)	0.086 (3)	0.043 (3)	0.027 (3)	0.012 (2)	0.005 (2)
C10	0.082 (4)	0.110 (5)	0.076 (4)	0.015 (3)	0.037 (3)	−0.001 (3)
C11	0.072 (3)	0.116 (4)	0.072 (4)	0.034 (3)	0.008 (3)	−0.001 (3)
C12	0.075 (4)	0.115 (5)	0.057 (3)	0.023 (3)	−0.002 (3)	0.003 (3)
C13	0.075 (3)	0.076 (3)	0.053 (3)	0.007 (3)	0.007 (2)	0.016 (2)

Geometric parameters (Å, º) top

N1—C1	1.344 (5)	C7—H7	0.9300
N1—N2	1.391 (4)	C8—C9	1.510 (6)
N1—H1	0.8600	C8—C13	1.516 (6)
N2—C8	1.277 (5)	C9—C10	1.493 (8)
O1—C1	1.236 (5)	C9—H9A	0.9700
O2—C3	1.373 (4)	C9—H9B	0.9700
O2—H2	0.8200	C10—C11	1.534 (9)
C1—C2	1.493 (5)	C10—H10A	0.9700
C2—C7	1.391 (5)	C10—H10B	0.9700
C2—C3	1.417 (4)	C11—C12	1.526 (9)
C3—C4	1.398 (5)	C11—H11A	0.9700
C4—C5	1.365 (6)	C11—H11B	0.9700
C4—H4	0.9300	C12—C13	1.486 (8)
C5—C6	1.394 (6)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C6—C7	1.370 (6)	C13—H13A	0.9700
C6—H6	0.9300	C13—H13B	0.9700

C1—N1—N2	118.4 (3)	C10—C9—H9A	109.4
C1—N1—H1	120.8	C8—C9—H9A	109.4
N2—N1—H1	120.8	C10—C9—H9B	109.4
C8—N2—N1	117.3 (3)	C8—C9—H9B	109.4
C3—O2—H2	109.5	H9A—C9—H9B	108.0
O1—C1—N1	122.2 (3)	C9—C10—C11	112.9 (5)
O1—C1—C2	120.3 (3)	C9—C10—H10A	109.0
N1—C1—C2	117.5 (3)	C11—C10—H10A	109.0
C7—C2—C3	117.3 (3)	C9—C10—H10B	109.0
C7—C2—C1	117.2 (3)	C11—C10—H10B	109.0
C3—C2—C1	125.4 (3)	H10A—C10—H10B	107.8
O2—C3—C4	119.8 (3)	C12—C11—C10	110.4 (5)
O2—C3—C2	119.9 (3)	C12—C11—H11A	109.6
C4—C3—C2	120.3 (3)	C10—C11—H11A	109.6
C5—C4—C3	120.1 (4)	C12—C11—H11B	109.6
C5—C4—H4	119.9	C10—C11—H11B	109.6
C3—C4—H4	119.9	H11A—C11—H11B	108.1
C4—C5—C6	120.5 (4)	C13—C12—C11	112.5 (5)
C4—C5—H5	119.7	C13—C12—H12A	109.1
C6—C5—H5	119.7	C11—C12—H12A	109.1
C7—C6—C5	119.4 (4)	C13—C12—H12B	109.1
C7—C6—H6	120.3	C11—C12—H12B	109.1
C5—C6—H6	120.3	H12A—C12—H12B	107.8
C6—C7—C2	122.3 (4)	C12—C13—C8	112.0 (5)
C6—C7—H7	118.8	C12—C13—H13A	109.2
C2—C7—H7	118.8	C8—C13—H13A	109.2
N2—C8—C9	128.0 (4)	C12—C13—H13B	109.2
N2—C8—C13	117.1 (4)	C8—C13—H13B	109.2
C9—C8—C13	114.8 (4)	H13A—C13—H13B	107.9
C10—C9—C8	111.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.97	2.655 (4)	136
O2—H2···O1ⁱ	0.82	2.15	2.704 (4)	125

Symmetry code: (i) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₂O₂
M_r	232.28
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	18.376 (2), 5.3386 (10), 12.9435 (15)
β (°)	102.241 (2)
V (Å³)	1240.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.39 × 0.29 × 0.27

Data collection
Diffractometer	Bruker SMART Apex CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.968, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	2969, 1090, 898
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.138, 1.08
No. of reflections	1090
No. of parameters	154
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.15

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.97	2.655 (4)	135.7
O2—H2···O1ⁱ	0.82	2.15	2.704 (4)	125.0

Symmetry code: (i) x, −y+1, z+1/2.

Acknowledgements

The author acknowledges the support of the National Natural Science Foundation of Liaocheng Vocational and Technical College (grant No. 081040).

References

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Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems Inc., Madison, Wisconsin, USA. Google Scholar
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