N'-(Cyclo-hexyl-carbon-yl)isonicotino-hydrazide.

In the title compound, C(13)H(17)N(3)O(2), the mean plane of the cyclo-hexane ring forms a dihedral angle of 33.12 (5)° with the pyridine ring. The two O atoms are twisted away from each other, as indicated by the C-N-N-C torsion angle of -74.97 (9)°. In the crystal structure, mol-ecules are linked into a three-dimensional network by inter-molecular N-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds. The structure is also stabilized by C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For applications of isoniazid derivatives, see: Janin (2007 ▶); Maccari et al. (2005 ▶); Slayden & Barry (2000 ▶). For the preparation, see: Besra et al. (1993 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H17N3O2

M = 247.30

Orthorhombic,

a = 9.1184 (2) Å

b = 11.5989 (2) Å

c = 12.1684 (2) Å

V = 1286.97 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.60 × 0.40 × 0.33 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.941, T max = 0.971

27969 measured reflections

3210 independent reflections

3124 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.084

S = 1.11

3210 reflections

231 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027469/kj2133sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027469/kj2133Isup2.hkl

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

C13H17N3O2	F(000) = 528
Mr = 247.30	Dx = 1.276 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9922 reflections
a = 9.1184 (2) Å	θ = 2.8–35.1°
b = 11.5989 (2) Å	µ = 0.09 mm−1
c = 12.1684 (2) Å	T = 100 K
V = 1286.97 (4) Å3	Block, colourless
Z = 4	0.60 × 0.40 × 0.33 mm

Bruker SMART APEXII CCD area-detector diffractometer	3210 independent reflections
Radiation source: fine-focus sealed tube	3124 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 35.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.941, Tmax = 0.971	k = −18→17
27969 measured reflections	l = −19→19

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.0754P] where P = (Fo2 + 2Fc2)/3
3210 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.75737 (8)	1.01913 (6)	1.03928 (5)	0.02041 (13)
O2	0.99005 (6)	0.79925 (5)	1.04401 (5)	0.01593 (11)
N1	1.02861 (8)	1.26064 (6)	0.76325 (6)	0.01714 (12)
N2	0.80178 (7)	0.89033 (6)	0.90156 (5)	0.01293 (11)
N3	0.76418 (7)	0.79834 (6)	0.96907 (5)	0.01347 (11)
C1	0.94236 (10)	1.18220 (7)	0.93422 (6)	0.01703 (14)
C2	1.01495 (11)	1.26604 (7)	0.87318 (7)	0.01889 (14)
C3	0.96940 (10)	1.16932 (7)	0.71250 (6)	0.01606 (13)
C4	0.89624 (9)	1.08036 (7)	0.76639 (6)	0.01426 (12)
C5	0.88303 (8)	1.08714 (6)	0.88042 (6)	0.01264 (12)
C6	0.80847 (8)	0.99670 (6)	0.94875 (6)	0.01322 (12)
C7	0.86549 (7)	0.75756 (6)	1.04018 (6)	0.01175 (11)
C8	0.81852 (8)	0.65554 (6)	1.10913 (6)	0.01238 (11)
C9	0.87614 (11)	0.54417 (7)	1.05682 (7)	0.02033 (15)
C10	0.83192 (15)	0.43958 (8)	1.12611 (10)	0.0300 (2)
C11	0.88525 (14)	0.45089 (10)	1.24449 (11)	0.0315 (2)
C12	0.82967 (13)	0.56214 (10)	1.29578 (7)	0.02597 (18)
C13	0.87382 (11)	0.66737 (8)	1.22748 (7)	0.02036 (15)
H1	0.936 (2)	1.1925 (16)	1.0135 (14)	0.033 (4)*
H2	1.062 (2)	1.3365 (15)	0.9082 (14)	0.032 (4)*
H3	0.9786 (19)	1.1702 (14)	0.6350 (14)	0.027 (4)*
H4	0.8560 (17)	1.0205 (13)	0.7227 (12)	0.018 (3)*
H8	0.7101 (18)	0.6508 (14)	1.1062 (12)	0.021 (3)*
H9A	0.837 (2)	0.5361 (17)	0.9849 (16)	0.042 (5)*
H9B	0.9813 (19)	0.5498 (15)	1.0523 (14)	0.028 (4)*
H10A	0.869 (2)	0.3690 (19)	1.0921 (16)	0.046 (5)*
H10B	0.722 (3)	0.4297 (19)	1.1277 (16)	0.047 (5)*
H11A	0.860 (2)	0.3808 (16)	1.2833 (14)	0.031 (4)*
H11B	0.995 (3)	0.454 (2)	1.249 (2)	0.053 (6)*
H12A	0.872 (2)	0.5711 (18)	1.3708 (15)	0.043 (5)*
H12B	0.722 (2)	0.5602 (16)	1.2991 (13)	0.032 (4)*
H13A	0.8388 (18)	0.7410 (13)	1.2598 (12)	0.018 (3)*
H13B	0.985 (2)	0.6778 (15)	1.2258 (14)	0.030 (4)*
H1N2	0.862 (2)	0.8724 (16)	0.8443 (15)	0.036 (5)*
H1N3	0.6729 (18)	0.7705 (13)	0.9596 (12)	0.022 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0286 (3)	0.0174 (3)	0.0152 (2)	0.0016 (2)	0.0095 (2)	0.0005 (2)
O2	0.0107 (2)	0.0156 (2)	0.0215 (2)	−0.00104 (18)	−0.00008 (19)	0.0012 (2)
N1	0.0205 (3)	0.0136 (2)	0.0173 (3)	−0.0004 (2)	0.0028 (2)	0.0031 (2)
N2	0.0148 (2)	0.0104 (2)	0.0135 (2)	−0.00010 (19)	0.00287 (19)	0.00212 (19)
N3	0.0116 (2)	0.0128 (2)	0.0159 (2)	−0.00129 (19)	−0.0005 (2)	0.0046 (2)
C1	0.0258 (3)	0.0126 (3)	0.0127 (3)	−0.0015 (3)	0.0022 (2)	−0.0006 (2)
C2	0.0263 (4)	0.0129 (3)	0.0175 (3)	−0.0031 (3)	0.0013 (3)	0.0000 (2)
C3	0.0198 (3)	0.0155 (3)	0.0129 (3)	0.0002 (3)	0.0022 (2)	0.0030 (2)
C4	0.0179 (3)	0.0133 (3)	0.0115 (2)	−0.0005 (2)	0.0009 (2)	0.0011 (2)
C5	0.0158 (3)	0.0107 (3)	0.0115 (2)	0.0009 (2)	0.0018 (2)	0.0012 (2)
C6	0.0149 (3)	0.0116 (3)	0.0131 (3)	0.0016 (2)	0.0026 (2)	0.0014 (2)
C7	0.0111 (2)	0.0111 (2)	0.0131 (2)	0.0007 (2)	0.0008 (2)	−0.0001 (2)
C8	0.0125 (2)	0.0115 (3)	0.0131 (3)	0.0003 (2)	0.0005 (2)	0.0015 (2)
C9	0.0292 (4)	0.0117 (3)	0.0202 (3)	−0.0009 (3)	0.0069 (3)	−0.0015 (2)
C10	0.0457 (6)	0.0107 (3)	0.0336 (5)	−0.0014 (4)	0.0128 (4)	0.0013 (3)
C11	0.0324 (5)	0.0236 (4)	0.0386 (5)	0.0063 (4)	0.0018 (4)	0.0171 (4)
C12	0.0337 (5)	0.0278 (4)	0.0164 (3)	−0.0030 (4)	−0.0022 (3)	0.0080 (3)
C13	0.0275 (4)	0.0196 (3)	0.0139 (3)	−0.0032 (3)	−0.0030 (3)	0.0010 (2)

O1—C6	1.2241 (9)	C7—C8	1.5125 (10)
O2—C7	1.2353 (9)	C8—C13	1.5321 (11)
N1—C3	1.3397 (11)	C8—C9	1.5329 (11)
N1—C2	1.3448 (11)	C8—H8	0.990 (16)
N2—C6	1.3622 (10)	C9—C10	1.5315 (13)
N2—N3	1.3895 (9)	C9—H9A	0.95 (2)
N2—H1N2	0.910 (19)	C9—H9B	0.963 (18)
N3—C7	1.3513 (9)	C10—C11	1.5260 (19)
N3—H1N3	0.900 (17)	C10—H10A	0.98 (2)
C1—C2	1.3912 (11)	C10—H10B	1.01 (2)
C1—C5	1.3917 (11)	C11—C12	1.5203 (18)
C1—H1	0.973 (18)	C11—H11A	0.967 (19)
C2—H2	1.017 (18)	C11—H11B	1.00 (3)
C3—C4	1.3927 (11)	C12—C13	1.5306 (13)
C3—H3	0.946 (17)	C12—H12A	0.997 (19)
C4—C5	1.3950 (10)	C12—H12B	0.98 (2)
C4—H4	0.948 (15)	C13—H13A	0.993 (15)
C5—C6	1.5014 (10)	C13—H13B	1.02 (2)
C3—N1—C2	117.26 (7)	C13—C8—H8	111.5 (8)
C6—N2—N3	117.22 (6)	C9—C8—H8	106.3 (9)
C6—N2—H1N2	120.2 (12)	C10—C9—C8	110.40 (7)
N3—N2—H1N2	115.2 (11)	C10—C9—H9A	109.4 (13)
C7—N3—N2	118.60 (6)	C8—C9—H9A	109.8 (13)
C7—N3—H1N3	126.1 (10)	C10—C9—H9B	110.4 (10)
N2—N3—H1N3	115.3 (10)	C8—C9—H9B	107.9 (11)
C2—C1—C5	119.18 (7)	H9A—C9—H9B	109.0 (17)
C2—C1—H1	118.0 (11)	C11—C10—C9	111.57 (9)
C5—C1—H1	122.8 (11)	C11—C10—H10A	111.1 (12)
N1—C2—C1	122.85 (8)	C9—C10—H10A	109.8 (12)
N1—C2—H2	114.5 (10)	C11—C10—H10B	107.9 (11)
C1—C2—H2	122.6 (10)	C9—C10—H10B	111.2 (12)
N1—C3—C4	124.18 (7)	H10A—C10—H10B	105.1 (17)
N1—C3—H3	114.5 (10)	C12—C11—C10	110.75 (8)
C4—C3—H3	121.3 (10)	C12—C11—H11A	115.7 (11)
C3—C4—C5	117.90 (7)	C10—C11—H11A	108.2 (11)
C3—C4—H4	117.7 (9)	C12—C11—H11B	106.4 (14)
C5—C4—H4	124.4 (9)	C10—C11—H11B	112.2 (15)
C1—C5—C4	118.62 (7)	H11A—C11—H11B	103.5 (18)
C1—C5—C6	117.98 (6)	C11—C12—C13	111.48 (8)
C4—C5—C6	123.41 (7)	C11—C12—H12A	109.6 (12)
O1—C6—N2	123.70 (7)	C13—C12—H12A	108.2 (12)
O1—C6—C5	121.48 (7)	C11—C12—H12B	109.3 (11)
N2—C6—C5	114.82 (6)	C13—C12—H12B	107.7 (11)
O2—C7—N3	121.04 (7)	H12A—C12—H12B	110.6 (16)
O2—C7—C8	123.07 (7)	C12—C13—C8	110.63 (7)
N3—C7—C8	115.81 (6)	C12—C13—H13A	112.7 (9)
C7—C8—C13	110.98 (6)	C8—C13—H13A	110.1 (9)
C7—C8—C9	109.38 (6)	C12—C13—H13B	111.5 (10)
C13—C8—C9	110.67 (7)	C8—C13—H13B	108.6 (9)
C7—C8—H8	107.9 (9)	H13A—C13—H13B	103.0 (14)
C6—N2—N3—C7	−74.97 (9)	N2—N3—C7—O2	−1.43 (11)
C3—N1—C2—C1	−0.37 (13)	N2—N3—C7—C8	−178.54 (6)
C5—C1—C2—N1	1.17 (14)	O2—C7—C8—C13	43.39 (10)
C2—N1—C3—C4	−0.43 (13)	N3—C7—C8—C13	−139.56 (7)
N1—C3—C4—C5	0.40 (13)	O2—C7—C8—C9	−79.00 (9)
C2—C1—C5—C4	−1.15 (12)	N3—C7—C8—C9	98.04 (8)
C2—C1—C5—C6	178.57 (8)	C7—C8—C9—C10	179.16 (8)
C3—C4—C5—C1	0.42 (12)	C13—C8—C9—C10	56.58 (10)
C3—C4—C5—C6	−179.29 (7)	C8—C9—C10—C11	−56.32 (12)
N3—N2—C6—O1	−14.45 (11)	C9—C10—C11—C12	55.80 (13)
N3—N2—C6—C5	166.16 (6)	C10—C11—C12—C13	−55.73 (12)
C1—C5—C6—O1	23.87 (12)	C11—C12—C13—C8	56.45 (11)
C4—C5—C6—O1	−156.42 (8)	C7—C8—C13—C12	−178.34 (7)
C1—C5—C6—N2	−156.72 (7)	C9—C8—C13—C12	−56.70 (10)
C4—C5—C6—N2	22.99 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N1i	0.911 (18)	2.095 (18)	2.9456 (10)	155.0 (16)
N3—H1N3···O2ii	0.900 (16)	1.854 (16)	2.7486 (9)	172.4 (14)
C2—H2···O1iii	1.017 (18)	2.527 (18)	3.4971 (11)	159.4 (14)
C4—H4···O1iv	0.948 (15)	2.502 (15)	3.3062 (10)	142.6 (12)
C10—H10B···Cg1v	1.01 (2)	2.78 (3)	3.7299 (14)	157.1 (16)
C13—H13A···Cg1vi	0.993 (15)	2.958 (16)	3.7039 (10)	132.7 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1i	0.911 (18)	2.095 (18)	2.9456 (10)	155.0 (16)
N3—H1N3⋯O2ii	0.900 (16)	1.854 (16)	2.7486 (9)	172.4 (14)
C2—H2⋯O1iii	1.017 (18)	2.527 (18)	3.4971 (11)	159.4 (14)
C4—H4⋯O1iv	0.948 (15)	2.502 (15)	3.3062 (10)	142.6 (12)
C10—H10B⋯Cg1v	1.01 (2)	2.78 (3)	3.7299 (14)	157.1 (16)
C13—H13A⋯Cg1vi	0.993 (15)	2.958 (16)	3.7039 (10)	132.7 (12)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 is the centroid of the C1/C2/N1/C3–C5 ring.