N'-Cyclo-hexyl-idenebenzohydrazide.

In the title compound, C(13)H(16)N(2)O, the cyclo-hexane ring adopts a chair conformation. In the crystal structure, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules 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 = 216.28

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.114

S = 1.08

1145 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052143/cv2665sup1.cif

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

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

C13H16N2O	Dx = 1.157 Mg m−3
Mr = 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

Bruker SMART APEX CCD area-detector diffractometer	1145 independent reflections
Radiation source: fine-focus sealed tube	860 reflections with I > 2σ(I)
graphite	Rint = 0.039
phi and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
Tmin = 0.968, Tmax = 0.980	k = −9→11
6248 measured reflections	l = −16→15

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(Fo2) + (0.0557P)2 + 0.1344P] where P = (Fo2 + 2Fc2)/3
1145 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.12 e Å−3
1 restraint	Δρmin = −0.13 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
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*

	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)

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

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

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) .