Crystal structure of 2-cyano-N'-(cyclo-hexyl-idene)acetohydrazide.

In the title compound, C9H13N3O, the cyclo-hexyl-idene ring adopts a chair conformation and the bond-angle sum at the C atom linked to the N atom is 359.6°. The cyano-acetohydrazide grouping is close to planar (r.m.s. deviation for the non-H atoms = 0.031 Å) and subtends a dihedral angle of 64.08 (4)° with the four C atoms forming the seat of the chair. The C=O and N-H groups are in a syn conformation (O-C-N-H = -5°). In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(8) loops; this dimer linkage is reinforced by a pair of C-H⋯O inter-actions, which generate R 2 (2)(14) loops. The dimers are linked by C-H⋯Nc (c = cyanide) inter-actions into [100] ladders, which feature C(4) chains and R 4 (4)(20) loops.

Related literature

For background to the role of hydrazides as potential anti-n class="Disease">cancer agents, see: Sechi et al. (2008 ▶); Manivel et al. (2009 ▶); Mohareb et al. (2011 ▶).

Experimental

Crystal data

C9H13N3O

M = 179.22

Triclinic,

a = 4.8420 (2) Å

b = 9.7407 (7) Å

c = 10.7071 (8) Å

α = 73.917 (9)°

β = 82.819 (10)°

γ = 75.980 (9)°

V = 469.87 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.13 × 0.12 × 0.04 mm

Data collection

Rigaku Mercury CCD diffractometer

6176 measured reflections

2136 independent reflections

1789 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.08

2136 reflections

121 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2012 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814009350/su0002sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009350/su0002Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814009350/su0002Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814009350/su0002fig1.tif

The mol­ecular structure of the title compound showing 50% displacement ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S1600536814009350/su0002fig2.tif

An inversion dimer in the crystal of the title compound, with N—H⋯O and C—H⋯O n class="Chemical">hydrogen bonds indicated by double-dashed lines. Symmetry code: (i) –x, 1–y, –z.

Click here for additional data file.

. DOI: 10.1107/S1600536814009350/su0002fig3.tif

Part of a [100] double chain in the crystal of the title compound, with hydrogen bonds indicated by double-dashed lines. Symmetry codes: (i) –x, 1–y, –z; (ii) 1+x, y, z.

CCDC reference: 1004279

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H13N3O	Z = 2
Mr = 179.22	F(000) = 192
Triclinic, P1	Dx = 1.267 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8420 (2) Å	Cell parameters from 5790 reflections
b = 9.7407 (7) Å	θ = 2.6–27.5°
c = 10.7071 (8) Å	µ = 0.09 mm−1
α = 73.917 (9)°	T = 100 K
β = 82.819 (10)°	Cut slab, yellow
γ = 75.980 (9)°	0.13 × 0.12 × 0.04 mm
V = 469.87 (5) Å3

Rigaku Mercury CCD diffractometer	1789 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
ω scans	h = −6→5
6176 measured reflections	k = −12→11
2136 independent reflections	l = −13→13

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.0762P] where P = (Fo2 + 2Fc2)/3
2136 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.19 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	0.5886 (2)	0.25153 (11)	0.23432 (10)	0.0172 (2)
C2	0.7514 (2)	0.14590 (11)	0.34545 (10)	0.0201 (2)
H2A	0.6664	0.1673	0.4289	0.024*
H2B	0.9522	0.1560	0.3350	0.024*
C3	0.7394 (2)	−0.01067 (12)	0.34647 (11)	0.0264 (3)
H3A	0.8587	−0.0815	0.4150	0.032*
H3B	0.5406	−0.0233	0.3673	0.032*
C4	0.8456 (3)	−0.04206 (13)	0.21466 (12)	0.0290 (3)
H4A	0.8225	−0.1407	0.2159	0.035*
H4B	1.0513	−0.0415	0.1989	0.035*
C5	0.6822 (2)	0.07141 (13)	0.10418 (11)	0.0272 (3)
H5A	0.4801	0.0636	0.1148	0.033*
H5B	0.7631	0.0511	0.0199	0.033*
C6	0.6986 (2)	0.22686 (12)	0.10284 (10)	0.0217 (2)
H6A	0.8983	0.2385	0.0843	0.026*
H6B	0.5815	0.2992	0.0343	0.026*
C7	−0.0539 (2)	0.51593 (11)	0.19148 (10)	0.0173 (2)
C8	−0.1182 (2)	0.51675 (11)	0.33402 (10)	0.0188 (2)
H8A	−0.1150	0.4156	0.3873	0.023*
H8B	0.0320	0.5522	0.3629	0.023*
C9	−0.3962 (2)	0.61033 (11)	0.35514 (10)	0.0190 (2)
N1	0.36168 (17)	0.33947 (9)	0.26408 (8)	0.0176 (2)
N2	0.19288 (17)	0.42828 (9)	0.16325 (8)	0.0183 (2)
H1	0.227 (3)	0.4221 (14)	0.0801 (14)	0.022*
N3	−0.61224 (19)	0.68227 (10)	0.37675 (9)	0.0251 (2)
O1	−0.21717 (15)	0.59183 (8)	0.10701 (7)	0.0228 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0182 (4)	0.0185 (5)	0.0157 (5)	−0.0059 (4)	−0.0009 (4)	−0.0038 (4)
C2	0.0207 (5)	0.0225 (5)	0.0153 (5)	−0.0025 (4)	−0.0019 (4)	−0.0038 (4)
C3	0.0310 (6)	0.0197 (5)	0.0229 (6)	−0.0032 (4)	0.0056 (5)	−0.0016 (4)
C4	0.0347 (6)	0.0210 (5)	0.0309 (6)	−0.0078 (4)	0.0109 (5)	−0.0102 (5)
C5	0.0217 (5)	0.0400 (7)	0.0266 (6)	−0.0090 (5)	0.0045 (4)	−0.0201 (5)
C6	0.0179 (5)	0.0282 (6)	0.0150 (5)	−0.0001 (4)	0.0000 (4)	−0.0036 (4)
C7	0.0189 (5)	0.0185 (5)	0.0151 (5)	−0.0058 (4)	0.0002 (4)	−0.0043 (4)
C8	0.0192 (5)	0.0217 (5)	0.0155 (5)	−0.0036 (4)	−0.0009 (4)	−0.0057 (4)
C9	0.0241 (5)	0.0199 (5)	0.0149 (5)	−0.0085 (4)	0.0000 (4)	−0.0050 (4)
N1	0.0196 (4)	0.0185 (4)	0.0142 (4)	−0.0041 (3)	−0.0031 (3)	−0.0027 (3)
N2	0.0196 (4)	0.0215 (5)	0.0118 (4)	−0.0018 (3)	−0.0011 (3)	−0.0034 (3)
N3	0.0253 (5)	0.0255 (5)	0.0240 (5)	−0.0037 (4)	0.0020 (4)	−0.0087 (4)
O1	0.0221 (4)	0.0263 (4)	0.0163 (4)	0.0009 (3)	−0.0027 (3)	−0.0043 (3)

C1—N1	1.2845 (13)	C5—H5A	0.99
C1—C2	1.5032 (14)	C5—H5B	0.99
C1—C6	1.5036 (14)	C6—H6A	0.99
C2—C3	1.5371 (15)	C6—H6B	0.99
C2—H2A	0.99	C7—O1	1.2306 (12)
C2—H2B	0.99	C7—N2	1.3442 (13)
C3—C4	1.5269 (16)	C7—C8	1.5209 (14)
C3—H3A	0.99	C8—C9	1.4622 (14)
C3—H3B	0.99	C8—H8A	0.99
C4—C5	1.5273 (17)	C8—H8B	0.99
C4—H4A	0.99	C9—N3	1.1457 (13)
C4—H4B	0.99	N1—N2	1.3938 (12)
C5—C6	1.5314 (16)	N2—H1	0.900 (14)
N1—C1—C2	116.83 (9)	C4—C5—H5B	109.4
N1—C1—C6	128.63 (9)	C6—C5—H5B	109.4
C2—C1—C6	114.13 (8)	H5A—C5—H5B	108.0
C1—C2—C3	108.83 (9)	C1—C6—C5	108.10 (9)
C1—C2—H2A	109.9	C1—C6—H6A	110.1
C3—C2—H2A	109.9	C5—C6—H6A	110.1
C1—C2—H2B	109.9	C1—C6—H6B	110.1
C3—C2—H2B	109.9	C5—C6—H6B	110.1
H2A—C2—H2B	108.3	H6A—C6—H6B	108.4
C4—C3—C2	111.01 (9)	O1—C7—N2	122.06 (9)
C4—C3—H3A	109.4	O1—C7—C8	121.97 (9)
C2—C3—H3A	109.4	N2—C7—C8	115.97 (9)
C4—C3—H3B	109.4	C9—C8—C7	111.64 (8)
C2—C3—H3B	109.4	C9—C8—H8A	109.3
H3A—C3—H3B	108.0	C7—C8—H8A	109.3
C3—C4—C5	111.44 (9)	C9—C8—H8B	109.3
C3—C4—H4A	109.3	C7—C8—H8B	109.3
C5—C4—H4A	109.3	H8A—C8—H8B	108.0
C3—C4—H4B	109.3	N3—C9—C8	177.32 (11)
C5—C4—H4B	109.3	C1—N1—N2	117.65 (9)
H4A—C4—H4B	108.0	C7—N2—N1	119.30 (9)
C4—C5—C6	111.25 (9)	C7—N2—H1	116.5 (8)
C4—C5—H5A	109.4	N1—N2—H1	123.6 (8)
C6—C5—H5A	109.4
N1—C1—C2—C3	114.56 (10)	O1—C7—C8—C9	3.02 (14)
C6—C1—C2—C3	−58.72 (11)	N2—C7—C8—C9	−177.51 (9)
C1—C2—C3—C4	54.68 (12)	C2—C1—N1—N2	−173.88 (8)
C2—C3—C4—C5	−54.91 (12)	C6—C1—N1—N2	−1.72 (16)
C3—C4—C5—C6	55.98 (12)	O1—C7—N2—N1	−176.79 (9)
N1—C1—C6—C5	−113.10 (12)	C8—C7—N2—N1	3.75 (13)
C2—C1—C6—C5	59.23 (11)	C1—N1—N2—C7	176.44 (9)
C4—C5—C6—C1	−56.13 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1i	0.900 (14)	2.052 (15)	2.9399 (12)	168.4 (11)
C6—H6B···O1i	0.99	2.32	3.2736 (13)	161
C8—H8B···N3ii	0.99	2.41	3.3783 (14)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1i	0.900 (14)	2.052 (15)	2.9399 (12)	168.4 (11)
C6—H6B⋯O1i	0.99	2.32	3.2736 (13)	161
C8—H8B⋯N3ii	0.99	2.41	3.3783 (14)	165

Symmetry codes: (i) ; (ii) .