(E)-N'-(2,4,6-Trimethyl-benzyl-idene)isonicotinohydrazide.

The title isoniazid derivative, C(16)H(17)N(3)O, exists in an E configuration with respect to the Schiff base C=N bond. The pyridine ring is essentially planar [maximum deviation = 0.009 (3) Å]. The mean plane through the hydrazide unit forms dihedral angles of 38.38 (16) and 39.42 (16)°, respectively, with the pyridine and benzene rings. In the crystal structure, symmetry-related mol-ecules are linked via inter-molecular N-H⋯O hydrogen bonds into chains along [100]. The crystal structure is further stabilized by weak inter-molecular C-H⋯π inter-actions.

Related literature

For general background to and applications of isoniazid derivatives, see: Janin (2007 ▶); Maccari et al. (2005 ▶); Slayden & Barry (2000 ▶); Kahwa et al. (1986 ▶). For the preparation of the title compound, see: Lourenco et al. (2008 ▶). For related structures, see: Naveenkumar et al. (2009 ▶, 2010 ▶); Shi (2005 ▶).

Experimental

Crystal data

C16H17N3O

M = 267.33

Monoclinic,

a = 4.7966 (7) Å

b = 34.268 (7) Å

c = 8.3795 (14) Å

β = 96.203 (14)°

V = 1369.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.35 × 0.10 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.994

12980 measured reflections

3127 independent reflections

2043 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.160

S = 1.11

3127 reflections

188 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536810019446/lh5051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019446/lh5051Isup2.hkl

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

C16H17N3O	F(000) = 568
Mr = 267.33	Dx = 1.297 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2541 reflections
a = 4.7966 (7) Å	θ = 2.4–30.0°
b = 34.268 (7) Å	µ = 0.08 mm−1
c = 8.3795 (14) Å	T = 100 K
β = 96.203 (14)°	Needle, colourless
V = 1369.3 (4) Å3	0.35 × 0.10 × 0.07 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	3127 independent reflections
Radiation source: fine-focus sealed tube	2043 reflections with I > 2σ(I)
graphite	Rint = 0.070
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.971, Tmax = 0.994	k = −44→43
12980 measured reflections	l = −10→10

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0432P)2 + 1.4572P] where P = (Fo2 + 2Fc2)/3
3127 reflections	(Δ/σ)max < 0.001
188 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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	0.9087 (4)	0.22119 (6)	0.3351 (3)	0.0317 (5)
N1	0.3263 (5)	0.34311 (7)	0.2703 (3)	0.0306 (6)
N2	0.4637 (5)	0.19838 (6)	0.2872 (3)	0.0213 (5)
N3	0.5529 (4)	0.16006 (6)	0.2958 (3)	0.0225 (5)
C1	0.3140 (5)	0.27683 (7)	0.1801 (3)	0.0219 (6)
H1A	0.2303	0.2581	0.1102	0.026*
C2	0.2194 (6)	0.31475 (8)	0.1741 (4)	0.0258 (6)
H2A	0.0708	0.3210	0.0977	0.031*
C3	0.5418 (6)	0.33331 (8)	0.3769 (4)	0.0329 (7)
H3A	0.6210	0.3526	0.4457	0.039*
C4	0.6534 (6)	0.29642 (8)	0.3909 (3)	0.0268 (6)
H4A	0.8062	0.2913	0.4660	0.032*
C5	0.5375 (5)	0.26708 (7)	0.2929 (3)	0.0213 (6)
C6	0.6561 (5)	0.22694 (8)	0.3077 (3)	0.0216 (6)
C7	0.3557 (5)	0.13476 (7)	0.2787 (3)	0.0225 (6)
H7A	0.1699	0.1429	0.2631	0.027*
C8	0.4207 (5)	0.09301 (7)	0.2837 (3)	0.0218 (6)
C9	0.6338 (5)	0.07743 (8)	0.3932 (3)	0.0230 (6)
C10	0.6948 (5)	0.03831 (8)	0.3826 (3)	0.0239 (6)
H10A	0.8364	0.0279	0.4547	0.029*
C11	0.5558 (5)	0.01384 (7)	0.2701 (3)	0.0219 (6)
C12	0.3405 (5)	0.02938 (7)	0.1670 (3)	0.0219 (6)
H12A	0.2411	0.0131	0.0924	0.026*
C13	0.2675 (5)	0.06847 (7)	0.1712 (3)	0.0212 (6)
C14	0.7896 (6)	0.10107 (8)	0.5253 (3)	0.0289 (7)
H14A	0.8591	0.0841	0.6117	0.043*
H14B	0.6652	0.1200	0.5639	0.043*
H14C	0.9440	0.1142	0.4848	0.043*
C15	0.6406 (6)	−0.02825 (8)	0.2617 (3)	0.0278 (6)
H15A	0.6317	−0.0403	0.3644	0.042*
H15C	0.8287	−0.0299	0.2331	0.042*
H15D	0.5155	−0.0415	0.1823	0.042*
C16	0.0339 (5)	0.08385 (8)	0.0537 (3)	0.0266 (6)
H16A	−0.0566	0.0625	−0.0053	0.040*
H16D	0.1094	0.1015	−0.0194	0.040*
H16B	−0.1001	0.0973	0.1108	0.040*
H1N2	0.271 (7)	0.2019 (8)	0.278 (4)	0.033 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0158 (10)	0.0349 (11)	0.0431 (13)	0.0011 (8)	−0.0035 (9)	0.0082 (9)
N1	0.0296 (14)	0.0280 (13)	0.0340 (15)	0.0002 (10)	0.0018 (11)	−0.0029 (11)
N2	0.0157 (12)	0.0217 (11)	0.0252 (13)	0.0021 (8)	−0.0035 (9)	0.0027 (9)
N3	0.0204 (12)	0.0230 (12)	0.0232 (13)	0.0026 (9)	−0.0012 (9)	0.0003 (9)
C1	0.0199 (13)	0.0243 (14)	0.0207 (15)	−0.0034 (10)	−0.0023 (11)	0.0017 (11)
C2	0.0199 (14)	0.0277 (15)	0.0287 (16)	0.0012 (11)	−0.0029 (12)	0.0033 (12)
C3	0.0346 (18)	0.0314 (16)	0.0317 (18)	−0.0073 (12)	−0.0013 (14)	−0.0062 (13)
C4	0.0228 (14)	0.0329 (16)	0.0227 (15)	−0.0039 (11)	−0.0068 (12)	0.0000 (12)
C5	0.0172 (13)	0.0267 (14)	0.0206 (14)	−0.0013 (10)	0.0039 (11)	0.0045 (11)
C6	0.0153 (13)	0.0291 (14)	0.0193 (14)	−0.0018 (10)	−0.0033 (11)	0.0048 (11)
C7	0.0163 (13)	0.0282 (14)	0.0226 (15)	0.0023 (10)	0.0007 (11)	0.0024 (11)
C8	0.0244 (14)	0.0175 (13)	0.0252 (15)	0.0002 (10)	0.0103 (12)	0.0013 (11)
C9	0.0224 (14)	0.0269 (14)	0.0200 (15)	−0.0015 (11)	0.0031 (11)	0.0018 (11)
C10	0.0203 (14)	0.0291 (15)	0.0213 (15)	0.0046 (10)	−0.0019 (11)	0.0046 (11)
C11	0.0211 (14)	0.0245 (14)	0.0205 (14)	−0.0005 (10)	0.0037 (11)	0.0016 (11)
C12	0.0206 (14)	0.0222 (13)	0.0231 (15)	−0.0016 (10)	0.0032 (11)	−0.0006 (11)
C13	0.0161 (13)	0.0243 (14)	0.0239 (15)	−0.0005 (10)	0.0059 (11)	0.0028 (11)
C14	0.0318 (16)	0.0275 (15)	0.0261 (16)	0.0015 (11)	−0.0028 (13)	0.0014 (12)
C15	0.0316 (16)	0.0277 (15)	0.0232 (16)	0.0053 (12)	−0.0018 (12)	0.0022 (12)
C16	0.0214 (14)	0.0246 (14)	0.0337 (17)	0.0007 (11)	0.0033 (12)	0.0015 (12)

O1—C6	1.225 (3)	C8—C13	1.409 (4)
N1—C2	1.330 (4)	C9—C10	1.377 (4)
N1—C3	1.334 (4)	C9—C14	1.504 (4)
N2—C6	1.343 (3)	C10—C11	1.378 (4)
N2—N3	1.380 (3)	C10—H10A	0.9300
N2—H1N2	0.93 (3)	C11—C12	1.380 (4)
N3—C7	1.280 (3)	C11—C15	1.502 (4)
C1—C2	1.375 (4)	C12—C13	1.386 (3)
C1—C5	1.391 (4)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C16	1.505 (4)
C2—H2A	0.9300	C14—H14A	0.9600
C3—C4	1.373 (4)	C14—H14B	0.9600
C3—H3A	0.9300	C14—H14C	0.9600
C4—C5	1.377 (4)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15C	0.9600
C5—C6	1.489 (4)	C15—H15D	0.9600
C7—C8	1.464 (4)	C16—H16A	0.9600
C7—H7A	0.9300	C16—H16D	0.9600
C8—C9	1.403 (4)	C16—H16B	0.9600
C2—N1—C3	116.2 (2)	C8—C9—C14	123.1 (2)
C6—N2—N3	118.8 (2)	C9—C10—C11	123.1 (3)
C6—N2—H1N2	125.5 (18)	C9—C10—H10A	118.5
N3—N2—H1N2	115.4 (18)	C11—C10—H10A	118.5
C7—N3—N2	114.7 (2)	C10—C11—C12	117.9 (2)
C2—C1—C5	118.6 (3)	C10—C11—C15	120.2 (2)
C2—C1—H1A	120.7	C12—C11—C15	122.0 (2)
C5—C1—H1A	120.7	C11—C12—C13	122.1 (3)
N1—C2—C1	124.4 (3)	C11—C12—H12A	119.0
N1—C2—H2A	117.8	C13—C12—H12A	119.0
C1—C2—H2A	117.8	C12—C13—C8	118.6 (2)
N1—C3—C4	123.8 (3)	C12—C13—C16	119.6 (2)
N1—C3—H3A	118.1	C8—C13—C16	121.8 (2)
C4—C3—H3A	118.1	C9—C14—H14A	109.5
C3—C4—C5	119.5 (3)	C9—C14—H14B	109.5
C3—C4—H4A	120.2	H14A—C14—H14B	109.5
C5—C4—H4A	120.2	C9—C14—H14C	109.5
C4—C5—C1	117.5 (2)	H14A—C14—H14C	109.5
C4—C5—C6	119.9 (2)	H14B—C14—H14C	109.5
C1—C5—C6	122.5 (2)	C11—C15—H15A	109.5
O1—C6—N2	124.0 (2)	C11—C15—H15C	109.5
O1—C6—C5	121.7 (2)	H15A—C15—H15C	109.5
N2—C6—C5	114.3 (2)	C11—C15—H15D	109.5
N3—C7—C8	120.4 (2)	H15A—C15—H15D	109.5
N3—C7—H7A	119.8	H15C—C15—H15D	109.5
C8—C7—H7A	119.8	C13—C16—H16A	109.5
C9—C8—C13	120.1 (2)	C13—C16—H16D	109.5
C9—C8—C7	121.9 (2)	H16A—C16—H16D	109.5
C13—C8—C7	118.0 (2)	C13—C16—H16B	109.5
C10—C9—C8	118.2 (2)	H16A—C16—H16B	109.5
C10—C9—C14	118.7 (2)	H16D—C16—H16B	109.5
C6—N2—N3—C7	178.4 (2)	N3—C7—C8—C13	−138.1 (3)
C3—N1—C2—C1	0.9 (4)	C13—C8—C9—C10	2.7 (4)
C5—C1—C2—N1	−0.5 (4)	C7—C8—C9—C10	−175.6 (2)
C2—N1—C3—C4	−0.1 (4)	C13—C8—C9—C14	−174.7 (2)
N1—C3—C4—C5	−1.2 (5)	C7—C8—C9—C14	7.1 (4)
C3—C4—C5—C1	1.7 (4)	C8—C9—C10—C11	−0.3 (4)
C3—C4—C5—C6	−179.7 (3)	C14—C9—C10—C11	177.2 (2)
C2—C1—C5—C4	−0.9 (4)	C9—C10—C11—C12	−1.9 (4)
C2—C1—C5—C6	−179.5 (2)	C9—C10—C11—C15	177.8 (3)
N3—N2—C6—O1	−0.6 (4)	C10—C11—C12—C13	1.8 (4)
N3—N2—C6—C5	178.9 (2)	C15—C11—C12—C13	−177.9 (2)
C4—C5—C6—O1	−37.5 (4)	C11—C12—C13—C8	0.6 (4)
C1—C5—C6—O1	141.0 (3)	C11—C12—C13—C16	178.9 (2)
C4—C5—C6—N2	142.9 (3)	C9—C8—C13—C12	−2.8 (4)
C1—C5—C6—N2	−38.5 (4)	C7—C8—C13—C12	175.5 (2)
N2—N3—C7—C8	179.4 (2)	C9—C8—C13—C16	178.9 (2)
N3—C7—C8—C9	40.1 (4)	C7—C8—C13—C16	−2.9 (4)

Cg1 is the centroid of the C1-C5/N1 pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.93 (3)	1.97 (3)	2.844 (3)	157 (3)
C16—H16B···Cg1i	0.96	2.96	3.551 (3)	121

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C5/N1 pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.93 (3)	1.97 (3)	2.844 (3)	157 (3)
C16—H16B⋯Cg1i	0.96	2.96	3.551 (3)	121

Symmetry code: (i) .