N′-Cyclo­hexyl­idenebenzohydrazide

Ju, X.; Qiao, Y.; Gao, Z.; Kong, L.

doi:10.1107/S1600536809052143

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o94

doi:10.1107/S1600536809052143

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N′-Cyclohexylidenebenzohydrazide

Xiuping Ju,^a Yan Qiao,^a Zhiqing Gao ^a and Lingqian Kong ^a ^*

^aDongchang College, Liaocheng University, Liaocheng 250059, People's Republic of China
^*Correspondence e-mail: konglingqian08@163.com

(Received 20 November 2009; accepted 3 December 2009; online 9 December 2009)

In the title compound, C₁₃H₁₆N₂O, the cyclohexane ring adopts a chair conformation. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains propagating in [001].

Related literature

For related structures, see: Fun et al. (2008 ); Nie (2008 ); Kong et al. (2009 ); Fan & Song (2009 ).

Experimental

Crystal data

C₁₃H₁₆N₂O
M_r = 216.28
Tetragonal, P 4₃
a = 9.4691 (11) Å
c = 13.8514 (15) Å
V = 1242.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.44 × 0.41 × 0.28 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.968, T_max = 0.980
6248 measured reflections
1145 independent reflections
860 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.114
S = 1.08
1145 reflections
145 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.28	3.133 (4)	172
C13—H13B⋯O1ⁱ	0.97	2.41	3.264 (5)	147
C7—H7⋯O1ⁱ	0.93	2.35	3.137 (5)	142
Symmetry code: (i) $[y, -x, z+{\script{1\over 4}}]$ .

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/S1600536809052143/cv2665sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052143/cv2665Isup2.hkl

checkCIF report

Comment top

In continuation of our structural study of benzohydrazide derivatives (Kong et al., 2009; Fan & Song, 2009), we present here the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the analogue compounds (Nie, 2008; Fun et al., 2008). The C8=N2 bond length is 1.283 (4) ° showing the double-bond character. The dihedral angle between the benzene ring C2—C7 and the plane C1/N1/N2 is 19.0 (3) °

In the crystal structure, intermolecular N—H···O and C—H..O hydrogen bonds (Table 1) link the molecules into chains propagated in direction [001].

Related literature top

For related structures, see: Fun et al. (2008); Nie (2008); Kong et al. (2009); Fan & Song (2009).

Experimental top

Cyclohexanone (5 mmol), benzohydrazide (5 mmol) and 10 ml of methanol were mixed in 50 ml flask. After stirring for 30 min at 373 K, the resulting mixture was recrystallized from methanol, affording the title compound as colourless crystalline solid. Elemental analysis: calculated for C₁₃H₁₆N₂O: C 72.19, H 7.46, N 12.95%; found: C 72.18, H 7.25, N 12.78%.

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. A view of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids,

(I) top

Crystal data top

C₁₃H₁₆N₂O	D_x = 1.157 Mg m⁻³
M_r = 216.28	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃	Cell parameters from 1861 reflections
a = 9.4691 (11) Å	θ = 2.6–21.7°
c = 13.8514 (15) Å	µ = 0.07 mm⁻¹
V = 1242.0 (2) Å³	T = 298 K
Z = 4	Block, colourless
F(000) = 464	0.44 × 0.41 × 0.28 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1145 independent reflections
Radiation source: fine-focus sealed tube	860 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
phi and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
T_min = 0.968, T_max = 0.980	k = −9→11
6248 measured reflections	l = −16→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0557P)² + 0.1344P] where P = (F_o² + 2F_c²)/3
1145 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.12 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₃H₁₆N₂O	Z = 4
M_r = 216.28	Mo Kα radiation
Tetragonal, P4₃	µ = 0.07 mm⁻¹
a = 9.4691 (11) Å	T = 298 K
c = 13.8514 (15) Å	0.44 × 0.41 × 0.28 mm
V = 1242.0 (2) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1145 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	860 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.980	R_int = 0.039
6248 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.114	H-atom parameters constrained
S = 1.08	Δρ_max = 0.12 e Å⁻³
1145 reflections	Δρ_min = −0.13 e Å⁻³
145 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	0.1658 (3)	0.0240 (3)	0.0959 (2)	0.0539 (7)
H1	0.1939	−0.0292	0.1423	0.065*
N2	0.0942 (3)	−0.0310 (3)	0.0148 (2)	0.0591 (8)
O1	0.1613 (3)	0.2405 (2)	0.02619 (18)	0.0664 (7)
C1	0.1877 (3)	0.1650 (3)	0.0965 (2)	0.0469 (7)
C2	0.2512 (3)	0.2288 (3)	0.1861 (2)	0.0476 (8)
C3	0.2322 (4)	0.3730 (4)	0.1997 (3)	0.0691 (10)
H3	0.1785	0.4244	0.1558	0.083*
C4	0.2925 (5)	0.4407 (5)	0.2780 (4)	0.0879 (14)
H4	0.2800	0.5374	0.2860	0.106*
C5	0.3704 (5)	0.3662 (5)	0.3435 (3)	0.0850 (13)
H5	0.4090	0.4120	0.3967	0.102*
C6	0.3921 (5)	0.2236 (5)	0.3311 (3)	0.0837 (13)
H6	0.4468	0.1733	0.3751	0.100*
C7	0.3317 (4)	0.1553 (4)	0.2525 (3)	0.0660 (10)
H7	0.3456	0.0588	0.2444	0.079*
C8	0.0953 (3)	−0.1653 (4)	0.0023 (3)	0.0571 (9)
C9	0.0175 (4)	−0.2201 (4)	−0.0853 (3)	0.0760 (12)
H9A	−0.0581	−0.2823	−0.0648	0.091*
H9B	−0.0242	−0.1415	−0.1200	0.091*
C10	0.1162 (5)	−0.2993 (5)	−0.1514 (4)	0.0919 (14)
H10A	0.1828	−0.2336	−0.1800	0.110*
H10B	0.0622	−0.3421	−0.2032	0.110*
C11	0.1973 (5)	−0.4143 (5)	−0.0971 (4)	0.0898 (14)
H11A	0.1320	−0.4873	−0.0767	0.108*
H11B	0.2659	−0.4570	−0.1401	0.108*
C12	0.2727 (5)	−0.3556 (4)	−0.0097 (3)	0.0824 (13)
H12A	0.3473	−0.2927	−0.0310	0.099*
H12B	0.3162	−0.4327	0.0255	0.099*
C13	0.1736 (5)	−0.2748 (4)	0.0584 (3)	0.0719 (11)
H13A	0.1073	−0.3397	0.0880	0.086*
H13B	0.2280	−0.2301	0.1093	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0677 (17)	0.0506 (16)	0.0435 (16)	−0.0033 (12)	−0.0078 (14)	0.0016 (13)
N2	0.0676 (18)	0.0586 (17)	0.0510 (18)	−0.0012 (14)	−0.0130 (14)	−0.0043 (15)
O1	0.0879 (17)	0.0622 (14)	0.0491 (16)	−0.0017 (12)	−0.0084 (13)	0.0105 (13)
C1	0.0479 (17)	0.0524 (19)	0.040 (2)	0.0022 (14)	0.0066 (15)	0.0005 (16)
C2	0.0538 (18)	0.0502 (18)	0.0389 (19)	−0.0028 (15)	0.0075 (15)	−0.0034 (15)
C3	0.084 (3)	0.059 (2)	0.065 (3)	0.0076 (18)	0.001 (2)	−0.0094 (19)
C4	0.106 (3)	0.066 (3)	0.092 (4)	0.001 (2)	0.005 (3)	−0.029 (3)
C5	0.102 (3)	0.097 (3)	0.056 (3)	−0.016 (3)	−0.003 (3)	−0.024 (3)
C6	0.102 (3)	0.087 (3)	0.061 (3)	−0.008 (2)	−0.023 (2)	−0.006 (2)
C7	0.077 (2)	0.063 (2)	0.058 (2)	−0.0037 (19)	−0.011 (2)	−0.0024 (19)
C8	0.063 (2)	0.055 (2)	0.053 (2)	−0.0060 (16)	0.0021 (17)	−0.0048 (17)
C9	0.083 (3)	0.069 (2)	0.076 (3)	−0.009 (2)	−0.020 (2)	−0.013 (2)
C10	0.123 (4)	0.090 (3)	0.062 (3)	−0.016 (3)	−0.009 (3)	−0.022 (3)
C11	0.103 (3)	0.079 (3)	0.088 (4)	−0.005 (2)	0.020 (3)	−0.024 (3)
C12	0.089 (3)	0.072 (2)	0.086 (3)	0.009 (2)	0.005 (3)	−0.006 (2)
C13	0.097 (3)	0.064 (2)	0.055 (2)	0.006 (2)	0.000 (2)	0.0009 (19)

Geometric parameters (Å, º) top

N1—C1	1.350 (4)	C8—C13	1.493 (5)
N1—N2	1.412 (4)	C8—C9	1.511 (5)
N1—H1	0.8600	C9—C10	1.508 (6)
N2—C8	1.283 (4)	C9—H9A	0.9700
O1—C1	1.234 (4)	C9—H9B	0.9700
C1—C2	1.506 (4)	C10—C11	1.530 (7)
C2—C7	1.382 (5)	C10—H10A	0.9700
C2—C3	1.390 (4)	C10—H10B	0.9700
C3—C4	1.383 (6)	C11—C12	1.511 (6)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.366 (7)	C11—H11B	0.9700
C4—H4	0.9300	C12—C13	1.535 (5)
C5—C6	1.377 (6)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C6—C7	1.390 (5)	C13—H13A	0.9700
C6—H6	0.9300	C13—H13B	0.9700
C7—H7	0.9300

C1—N1—N2	116.3 (3)	C10—C9—H9A	109.5
C1—N1—H1	121.8	C8—C9—H9A	109.5
N2—N1—H1	121.8	C10—C9—H9B	109.5
C8—N2—N1	118.0 (3)	C8—C9—H9B	109.5
O1—C1—N1	122.5 (3)	H9A—C9—H9B	108.0
O1—C1—C2	119.9 (3)	C9—C10—C11	111.5 (4)
N1—C1—C2	117.6 (3)	C9—C10—H10A	109.3
C7—C2—C3	118.4 (3)	C11—C10—H10A	109.3
C7—C2—C1	124.5 (3)	C9—C10—H10B	109.3
C3—C2—C1	117.0 (3)	C11—C10—H10B	109.3
C4—C3—C2	120.5 (4)	H10A—C10—H10B	108.0
C4—C3—H3	119.7	C12—C11—C10	111.7 (4)
C2—C3—H3	119.7	C12—C11—H11A	109.3
C5—C4—C3	120.3 (4)	C10—C11—H11A	109.3
C5—C4—H4	119.9	C12—C11—H11B	109.3
C3—C4—H4	119.9	C10—C11—H11B	109.3
C4—C5—C6	120.3 (4)	H11A—C11—H11B	107.9
C4—C5—H5	119.8	C11—C12—C13	112.8 (3)
C6—C5—H5	119.8	C11—C12—H12A	109.0
C5—C6—C7	119.5 (4)	C13—C12—H12A	109.0
C5—C6—H6	120.3	C11—C12—H12B	109.0
C7—C6—H6	120.3	C13—C12—H12B	109.0
C2—C7—C6	120.9 (4)	H12A—C12—H12B	107.8
C2—C7—H7	119.5	C8—C13—C12	109.2 (3)
C6—C7—H7	119.5	C8—C13—H13A	109.8
N2—C8—C13	128.4 (3)	C12—C13—H13A	109.8
N2—C8—C9	116.4 (3)	C8—C13—H13B	109.8
C13—C8—C9	114.9 (3)	C12—C13—H13B	109.8
C10—C9—C8	110.9 (3)	H13A—C13—H13B	108.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.28	3.133 (4)	172
C13—H13B···O1ⁱ	0.97	2.41	3.264 (5)	147
C7—H7···O1ⁱ	0.93	2.35	3.137 (5)	142

Symmetry code: (i) y, −x, z+1/4.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₂O
M_r	216.28
Crystal system, space group	Tetragonal, P4₃
Temperature (K)	298
a, c (Å)	9.4691 (11), 13.8514 (15)
V (Å³)	1242.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.44 × 0.41 × 0.28

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.968, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	6248, 1145, 860
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.114, 1.08
No. of reflections	1145
No. of parameters	145
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.13

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···O1ⁱ	0.86	2.28	3.133 (4)	172.1
C13—H13B···O1ⁱ	0.97	2.41	3.264 (5)	147.4
C7—H7···O1ⁱ	0.93	2.35	3.137 (5)	142.0

Symmetry code: (i) y, −x, z+1/4.

Acknowledgements

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

References

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