(E)-N'-(2,3,4-Trimethoxy-benzyl-idene)isonicotinohydrazide.

In the title compound, C(16)H(17)N(3)O(4), the mol-ecule exists in an E configuration with respect to the C=N double bond. The mol-ecule is not planar, the dihedral angle between the pyridine and benzene rings being 71.67 (8)°. In the crystal structure, mol-ecules are linked into chains along the b axis by bifurcated N-H⋯O and C-H⋯O hydrogen bonds. These chains are linked into a three-dimensional network by C-H⋯O and C-H⋯π inter-actions.

Related literature

For applications of isoniazid derivatives, see: Janin (2007 ▶); Maccari et al. (2005 ▶); Slayden & Barry (2000 ▶); Kahwa et al. (1986 ▶). For preparation of the compound, see: Lourenco et al. (2008 ▶). For related structures, see: Naveenkumar et al. (2009 ▶, 2010a ▶,b ▶); Shi (2005 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H17N3O4

M = 315.33

Monoclinic,

a = 14.246 (3) Å

b = 9.397 (2) Å

c = 12.098 (3) Å

β = 109.245 (6)°

V = 1529.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.38 × 0.33 × 0.14 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.986

14341 measured reflections

3482 independent reflections

2988 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.159

S = 1.10

3482 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.38 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/S1600536810015266/tk2657sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015266/tk2657Isup2.hkl

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

C16H17N3O4	F(000) = 664
Mr = 315.33	Dx = 1.370 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5847 reflections
a = 14.246 (3) Å	θ = 2.8–33.0°
b = 9.397 (2) Å	µ = 0.10 mm−1
c = 12.098 (3) Å	T = 100 K
β = 109.245 (6)°	Block, colourless
V = 1529.1 (6) Å3	0.38 × 0.33 × 0.14 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	3482 independent reflections
Radiation source: fine-focus sealed tube	2988 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→18
Tmin = 0.963, Tmax = 0.986	k = −11→12
14341 measured reflections	l = −15→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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0903P)2 + 0.7464P] where P = (Fo2 + 2Fc2)/3
3482 reflections	(Δ/σ)max < 0.001
215 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.38 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	0.01090 (9)	0.86823 (12)	−0.28320 (11)	0.0286 (3)
O2	0.36424 (9)	0.41851 (12)	−0.00731 (10)	0.0232 (3)
O3	0.47223 (8)	0.40332 (13)	0.23303 (10)	0.0235 (3)
O4	0.41436 (9)	0.55428 (13)	0.38640 (10)	0.0245 (3)
N1	−0.18863 (12)	0.63126 (17)	−0.66119 (13)	0.0302 (4)
N2	0.05989 (10)	0.63755 (14)	−0.24901 (12)	0.0207 (3)
N3	0.11895 (10)	0.66421 (14)	−0.13400 (11)	0.0208 (3)
C1	−0.08316 (12)	0.79807 (18)	−0.52380 (15)	0.0238 (3)
H1A	−0.0557	0.8888	−0.5098	0.029*
C2	−0.14580 (13)	0.76010 (19)	−0.63502 (15)	0.0277 (4)
H2A	−0.1587	0.8275	−0.6944	0.033*
C3	−0.16847 (13)	0.53782 (19)	−0.57329 (15)	0.0278 (4)
H3A	−0.1983	0.4487	−0.5894	0.033*
C4	−0.10626 (12)	0.56370 (17)	−0.45947 (15)	0.0231 (3)
H4A	−0.0942	0.4937	−0.4021	0.028*
C5	−0.06239 (11)	0.69824 (17)	−0.43404 (14)	0.0204 (3)
C6	0.00512 (11)	0.74314 (16)	−0.31422 (14)	0.0203 (3)
C7	0.18304 (11)	0.56473 (17)	−0.09093 (13)	0.0200 (3)
H7A	0.1910	0.4914	−0.1387	0.024*
C8	0.24315 (11)	0.56734 (16)	0.03316 (14)	0.0198 (3)
C9	0.33100 (11)	0.48599 (16)	0.07346 (13)	0.0184 (3)
C10	0.38660 (11)	0.48299 (16)	0.19251 (13)	0.0188 (3)
C11	0.35435 (12)	0.56152 (17)	0.27246 (14)	0.0205 (3)
C12	0.26610 (12)	0.63962 (17)	0.23309 (15)	0.0233 (3)
H12A	0.2438	0.6895	0.2860	0.028*
C13	0.21207 (12)	0.64218 (17)	0.11454 (14)	0.0229 (3)
H13A	0.1537	0.6951	0.0886	0.027*
C14	0.35843 (15)	0.26623 (19)	−0.00823 (17)	0.0325 (4)
H14A	0.3768	0.2297	−0.0723	0.049*
H14B	0.2917	0.2376	−0.0171	0.049*
H14C	0.4029	0.2294	0.0641	0.049*
C15	0.55771 (13)	0.4749 (2)	0.22131 (17)	0.0324 (4)
H15A	0.6152	0.4152	0.2516	0.049*
H15B	0.5682	0.5626	0.2644	0.049*
H15C	0.5468	0.4945	0.1401	0.049*
C16	0.38727 (14)	0.6398 (2)	0.46951 (15)	0.0308 (4)
H16A	0.4343	0.6248	0.5463	0.046*
H16B	0.3221	0.6132	0.4690	0.046*
H16C	0.3873	0.7384	0.4488	0.046*
H1N2	0.0529 (18)	0.544 (3)	−0.270 (2)	0.038 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0297 (6)	0.0180 (6)	0.0300 (6)	0.0029 (5)	−0.0011 (5)	−0.0029 (5)
O2	0.0270 (6)	0.0225 (6)	0.0204 (6)	0.0008 (4)	0.0083 (5)	−0.0008 (4)
O3	0.0192 (6)	0.0264 (6)	0.0232 (6)	0.0059 (4)	0.0047 (4)	0.0030 (4)
O4	0.0264 (6)	0.0278 (6)	0.0176 (6)	0.0044 (5)	0.0048 (5)	−0.0011 (4)
N1	0.0324 (8)	0.0321 (8)	0.0239 (7)	0.0010 (6)	0.0062 (6)	−0.0048 (6)
N2	0.0224 (7)	0.0167 (6)	0.0202 (6)	0.0005 (5)	0.0032 (5)	−0.0022 (5)
N3	0.0217 (6)	0.0189 (6)	0.0200 (6)	−0.0027 (5)	0.0045 (5)	−0.0024 (5)
C1	0.0234 (7)	0.0205 (8)	0.0288 (8)	0.0018 (6)	0.0104 (6)	0.0013 (6)
C2	0.0306 (9)	0.0289 (9)	0.0244 (8)	0.0040 (7)	0.0101 (7)	0.0026 (6)
C3	0.0276 (8)	0.0244 (8)	0.0285 (8)	−0.0007 (7)	0.0055 (7)	−0.0062 (7)
C4	0.0214 (7)	0.0200 (8)	0.0272 (8)	0.0014 (6)	0.0071 (6)	0.0000 (6)
C5	0.0181 (7)	0.0197 (7)	0.0243 (8)	0.0031 (6)	0.0080 (6)	−0.0013 (6)
C6	0.0178 (7)	0.0172 (7)	0.0257 (8)	0.0011 (6)	0.0069 (6)	−0.0006 (6)
C7	0.0201 (7)	0.0191 (7)	0.0201 (7)	−0.0028 (6)	0.0054 (6)	−0.0004 (5)
C8	0.0192 (7)	0.0175 (7)	0.0211 (7)	−0.0023 (6)	0.0044 (6)	0.0028 (5)
C9	0.0198 (7)	0.0160 (7)	0.0197 (7)	−0.0020 (5)	0.0069 (6)	0.0004 (5)
C10	0.0175 (7)	0.0170 (7)	0.0212 (7)	0.0014 (5)	0.0054 (6)	0.0021 (5)
C11	0.0222 (7)	0.0195 (7)	0.0192 (7)	−0.0006 (6)	0.0059 (6)	0.0013 (6)
C12	0.0242 (8)	0.0227 (8)	0.0236 (8)	0.0035 (6)	0.0088 (6)	−0.0016 (6)
C13	0.0216 (7)	0.0199 (8)	0.0259 (8)	0.0026 (6)	0.0061 (6)	0.0019 (6)
C14	0.0394 (10)	0.0229 (9)	0.0378 (10)	0.0001 (7)	0.0165 (8)	−0.0068 (7)
C15	0.0205 (8)	0.0433 (11)	0.0336 (9)	0.0019 (7)	0.0092 (7)	0.0000 (8)
C16	0.0330 (9)	0.0381 (10)	0.0211 (8)	0.0055 (8)	0.0086 (7)	−0.0035 (7)

O1—C6	1.228 (2)	C5—C6	1.512 (2)
O2—C9	1.3733 (19)	C7—C8	1.463 (2)
O2—C14	1.433 (2)	C7—H7A	0.9300
O3—C10	1.3765 (18)	C8—C13	1.395 (2)
O3—C15	1.438 (2)	C8—C9	1.409 (2)
O4—C11	1.3634 (19)	C9—C10	1.397 (2)
O4—C16	1.436 (2)	C10—C11	1.409 (2)
N1—C3	1.335 (2)	C11—C12	1.397 (2)
N1—C2	1.346 (2)	C12—C13	1.387 (2)
N2—C6	1.345 (2)	C12—H12A	0.9300
N2—N3	1.3910 (18)	C13—H13A	0.9300
N2—H1N2	0.91 (3)	C14—H14A	0.9600
N3—C7	1.290 (2)	C14—H14B	0.9600
C1—C5	1.391 (2)	C14—H14C	0.9600
C1—C2	1.394 (2)	C15—H15A	0.9600
C1—H1A	0.9300	C15—H15B	0.9600
C2—H2A	0.9300	C15—H15C	0.9600
C3—C4	1.391 (2)	C16—H16A	0.9600
C3—H3A	0.9300	C16—H16B	0.9600
C4—C5	1.399 (2)	C16—H16C	0.9600
C4—H4A	0.9300
C9—O2—C14	115.72 (13)	O2—C9—C8	118.64 (14)
C10—O3—C15	112.99 (13)	C10—C9—C8	120.32 (14)
C11—O4—C16	117.16 (13)	O3—C10—C9	120.87 (14)
C3—N1—C2	116.26 (15)	O3—C10—C11	119.46 (13)
C6—N2—N3	119.77 (13)	C9—C10—C11	119.68 (14)
C6—N2—H1N2	124.0 (15)	O4—C11—C12	124.39 (15)
N3—N2—H1N2	115.3 (15)	O4—C11—C10	115.49 (14)
C7—N3—N2	112.81 (13)	C12—C11—C10	120.11 (15)
C5—C1—C2	119.00 (16)	C13—C12—C11	119.48 (15)
C5—C1—H1A	120.5	C13—C12—H12A	120.3
C2—C1—H1A	120.5	C11—C12—H12A	120.3
N1—C2—C1	123.62 (16)	C12—C13—C8	121.61 (15)
N1—C2—H2A	118.2	C12—C13—H13A	119.2
C1—C2—H2A	118.2	C8—C13—H13A	119.2
N1—C3—C4	124.95 (16)	O2—C14—H14A	109.5
N1—C3—H3A	117.5	O2—C14—H14B	109.5
C4—C3—H3A	117.5	H14A—C14—H14B	109.5
C3—C4—C5	117.92 (16)	O2—C14—H14C	109.5
C3—C4—H4A	121.0	H14A—C14—H14C	109.5
C5—C4—H4A	121.0	H14B—C14—H14C	109.5
C1—C5—C4	118.23 (15)	O3—C15—H15A	109.5
C1—C5—C6	117.70 (15)	O3—C15—H15B	109.5
C4—C5—C6	124.06 (15)	H15A—C15—H15B	109.5
O1—C6—N2	123.99 (15)	O3—C15—H15C	109.5
O1—C6—C5	121.16 (14)	H15A—C15—H15C	109.5
N2—C6—C5	114.79 (14)	H15B—C15—H15C	109.5
N3—C7—C8	119.94 (14)	O4—C16—H16A	109.5
N3—C7—H7A	120.0	O4—C16—H16B	109.5
C8—C7—H7A	120.0	H16A—C16—H16B	109.5
C13—C8—C9	118.77 (14)	O4—C16—H16C	109.5
C13—C8—C7	121.20 (14)	H16A—C16—H16C	109.5
C9—C8—C7	119.90 (14)	H16B—C16—H16C	109.5
O2—C9—C10	120.87 (13)
C6—N2—N3—C7	−165.58 (14)	C7—C8—C9—O2	7.4 (2)
C3—N1—C2—C1	0.3 (3)	C13—C8—C9—C10	−1.2 (2)
C5—C1—C2—N1	0.5 (3)	C7—C8—C9—C10	−177.24 (14)
C2—N1—C3—C4	−1.0 (3)	C15—O3—C10—C9	82.69 (18)
N1—C3—C4—C5	1.0 (3)	C15—O3—C10—C11	−97.83 (17)
C2—C1—C5—C4	−0.5 (2)	O2—C9—C10—O3	−5.1 (2)
C2—C1—C5—C6	−179.50 (14)	C8—C9—C10—O3	179.63 (14)
C3—C4—C5—C1	−0.2 (2)	O2—C9—C10—C11	175.45 (14)
C3—C4—C5—C6	178.75 (15)	C8—C9—C10—C11	0.2 (2)
N3—N2—C6—O1	7.8 (2)	C16—O4—C11—C12	−3.8 (2)
N3—N2—C6—C5	−175.09 (13)	C16—O4—C11—C10	176.28 (14)
C1—C5—C6—O1	27.6 (2)	O3—C10—C11—O4	1.7 (2)
C4—C5—C6—O1	−151.38 (17)	C9—C10—C11—O4	−178.79 (13)
C1—C5—C6—N2	−149.60 (15)	O3—C10—C11—C12	−178.17 (14)
C4—C5—C6—N2	31.5 (2)	C9—C10—C11—C12	1.3 (2)
N2—N3—C7—C8	−172.80 (13)	O4—C11—C12—C13	178.42 (15)
N3—C7—C8—C13	22.4 (2)	C10—C11—C12—C13	−1.7 (2)
N3—C7—C8—C9	−161.70 (15)	C11—C12—C13—C8	0.6 (2)
C14—O2—C9—C10	73.23 (19)	C9—C8—C13—C12	0.8 (2)
C14—O2—C9—C8	−111.40 (16)	C7—C8—C13—C12	176.81 (15)
C13—C8—C9—O2	−176.62 (14)

Cg1 is centroid of the C1/C2/N1/C3/C4/C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.91 (3)	2.09 (3)	2.7987 (19)	134 (2)
C4—H4A···O1i	0.93	2.46	3.348 (2)	159
C14—H14C···O3	0.96	2.55	3.113 (2)	118
C15—H15C···O2ii	0.96	2.49	3.292 (2)	141
C16—H16A···O3iii	0.96	2.57	3.518 (2)	167
C14—H14B···Cg1i	0.96	2.81	3.719 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1/C2/N1/C3/C4/C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.91 (3)	2.09 (3)	2.7987 (19)	134 (2)
C4—H4A⋯O1i	0.93	2.46	3.348 (2)	159
C14—H14C⋯O3	0.96	2.55	3.113 (2)	118
C15—H15C⋯O2ii	0.96	2.49	3.292 (2)	141
C16—H16A⋯O3iii	0.96	2.57	3.518 (2)	167
C14—H14B⋯Cg1i	0.96	2.81	3.719 (3)	159

Symmetry codes: (i) ; (ii) ; (iii) .