(E)-N'-[(E)-3-(4-Hydr-oxy-3-methoxy-phen-yl)allyl-idene]isonicotinohydrazide.

In the title compound, C(16)H(15)N(3)O(3), the dihedral angle between the pyridine and benzene rings is 7.66 (5)°. The crystal packing is consolidated by inter-molecular C-H⋯O and O-H⋯N inter-actions, which link the mol-ecules into zigzag chains propagating along [010]. The chains are further linked into a three-dimensional network by N-H⋯O, C-H⋯N, C-H⋯O and C-H⋯π inter-actions.

Related literature

For the synthesis, see: Lourenco et al. (2008 ▶). For the tuberculostatic activities of isoniazid derivatives, see: Janin (2007 ▶). For related structures, see: Naveenkumar et al. (2009a ▶,b ▶,c ▶); Shi (2005 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H15N3O3

M = 297.31

Monoclinic,

a = 5.0470 (1) Å

b = 28.9314 (6) Å

c = 9.6446 (2) Å

β = 90.010 (1)°

V = 1408.27 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.53 × 0.20 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.950, T max = 0.992

33857 measured reflections

4144 independent reflections

3534 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.110

S = 1.05

4144 reflections

208 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.22 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/S1600536810000371/hb5304sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000371/hb5304Isup2.hkl

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

C16H15N3O3	F(000) = 624
Mr = 297.31	Dx = 1.402 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9970 reflections
a = 5.0470 (1) Å	θ = 2.2–30.1°
b = 28.9314 (6) Å	µ = 0.10 mm−1
c = 9.6446 (2) Å	T = 100 K
β = 90.010 (1)°	Needle, yellow
V = 1408.27 (5) Å3	0.53 × 0.20 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4144 independent reflections
Radiation source: fine-focus sealed tube	3534 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 30.2°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.950, Tmax = 0.992	k = −40→40
33857 measured 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0505P)2 + 0.5887P] where P = (Fo2 + 2Fc2)/3
4144 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.22 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	1.08233 (15)	0.46282 (3)	0.88942 (9)	0.01916 (18)
O2	0.21767 (17)	0.74390 (3)	0.22611 (9)	0.01855 (18)
O3	0.60188 (15)	0.73516 (3)	0.41721 (8)	0.01721 (17)
N1	0.7016 (2)	0.32923 (3)	1.14947 (11)	0.0203 (2)
N2	0.64104 (19)	0.47193 (3)	0.84655 (10)	0.01645 (19)
N3	0.68169 (19)	0.51003 (3)	0.76213 (10)	0.0175 (2)
C1	0.5730 (2)	0.38057 (4)	0.96577 (15)	0.0242 (3)
H1A	0.4555	0.3873	0.8943	0.029*
C2	0.5420 (2)	0.34088 (4)	1.04462 (15)	0.0260 (3)
H2A	0.4020	0.3212	1.0233	0.031*
C3	0.8987 (3)	0.35853 (4)	1.17893 (13)	0.0235 (3)
H3A	1.0093	0.3515	1.2531	0.028*
C4	0.9479 (2)	0.39885 (4)	1.10550 (12)	0.0213 (2)
H4A	1.0887	0.4180	1.1294	0.026*
C5	0.7823 (2)	0.41004 (4)	0.99545 (11)	0.0149 (2)
C6	0.8505 (2)	0.45104 (4)	0.90682 (11)	0.0144 (2)
C7	0.4745 (2)	0.52317 (4)	0.69452 (12)	0.0179 (2)
H7A	0.3181	0.5063	0.7002	0.021*
C8	0.4869 (2)	0.56419 (4)	0.61002 (12)	0.0184 (2)
H8A	0.6425	0.5814	0.6096	0.022*
C9	0.2819 (2)	0.57851 (4)	0.53159 (12)	0.0181 (2)
H9A	0.1349	0.5592	0.5273	0.022*
C10	0.2689 (2)	0.62152 (4)	0.45276 (11)	0.0158 (2)
C11	0.4478 (2)	0.65790 (4)	0.47779 (11)	0.0158 (2)
H11A	0.5762	0.6546	0.5463	0.019*
C12	0.4357 (2)	0.69838 (4)	0.40220 (11)	0.0141 (2)
C13	0.2379 (2)	0.70419 (4)	0.29982 (11)	0.0144 (2)
C14	0.0603 (2)	0.66845 (4)	0.27564 (12)	0.0173 (2)
H14A	−0.0695	0.6719	0.2080	0.021*
C15	0.0737 (2)	0.62759 (4)	0.35120 (12)	0.0173 (2)
H15A	−0.0478	0.6041	0.3342	0.021*
C16	0.7875 (2)	0.73391 (4)	0.52991 (12)	0.0176 (2)
H16A	0.9059	0.7598	0.5229	0.026*
H16B	0.8873	0.7057	0.5259	0.026*
H16C	0.6934	0.7354	0.6163	0.026*
H1N2	0.476 (3)	0.4640 (5)	0.8667 (16)	0.025 (4)*
H1O2	0.284 (4)	0.7669 (7)	0.272 (2)	0.048 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0127 (4)	0.0203 (4)	0.0245 (4)	−0.0018 (3)	0.0008 (3)	0.0028 (3)
O2	0.0221 (4)	0.0158 (4)	0.0178 (4)	−0.0010 (3)	−0.0061 (3)	0.0024 (3)
O3	0.0162 (4)	0.0151 (4)	0.0203 (4)	−0.0022 (3)	−0.0061 (3)	0.0015 (3)
N1	0.0241 (5)	0.0162 (5)	0.0204 (5)	−0.0010 (4)	0.0014 (4)	0.0014 (4)
N2	0.0127 (4)	0.0140 (4)	0.0226 (5)	−0.0011 (3)	0.0009 (3)	0.0045 (4)
N3	0.0172 (4)	0.0131 (4)	0.0221 (5)	−0.0014 (3)	0.0008 (3)	0.0035 (4)
C1	0.0188 (5)	0.0180 (6)	0.0358 (7)	−0.0030 (4)	−0.0089 (5)	0.0068 (5)
C2	0.0201 (6)	0.0178 (6)	0.0400 (7)	−0.0052 (4)	−0.0061 (5)	0.0068 (5)
C3	0.0312 (6)	0.0218 (6)	0.0175 (5)	−0.0057 (5)	−0.0059 (4)	0.0030 (5)
C4	0.0249 (6)	0.0206 (6)	0.0183 (5)	−0.0066 (4)	−0.0042 (4)	0.0012 (4)
C5	0.0139 (5)	0.0130 (5)	0.0178 (5)	0.0010 (4)	0.0029 (4)	−0.0013 (4)
C6	0.0139 (5)	0.0128 (5)	0.0163 (5)	−0.0004 (4)	0.0009 (4)	−0.0009 (4)
C7	0.0162 (5)	0.0154 (5)	0.0220 (5)	−0.0018 (4)	0.0009 (4)	0.0018 (4)
C8	0.0169 (5)	0.0154 (5)	0.0228 (6)	−0.0009 (4)	0.0011 (4)	0.0025 (4)
C9	0.0170 (5)	0.0153 (5)	0.0221 (6)	−0.0014 (4)	0.0006 (4)	0.0018 (4)
C10	0.0154 (5)	0.0155 (5)	0.0166 (5)	0.0012 (4)	0.0008 (4)	0.0006 (4)
C11	0.0136 (5)	0.0168 (5)	0.0171 (5)	0.0015 (4)	−0.0021 (4)	0.0010 (4)
C12	0.0124 (4)	0.0149 (5)	0.0149 (5)	0.0004 (4)	0.0003 (3)	−0.0018 (4)
C13	0.0157 (5)	0.0152 (5)	0.0122 (5)	0.0018 (4)	−0.0003 (3)	−0.0003 (4)
C14	0.0178 (5)	0.0186 (5)	0.0155 (5)	−0.0005 (4)	−0.0042 (4)	−0.0015 (4)
C15	0.0166 (5)	0.0164 (5)	0.0190 (5)	−0.0018 (4)	−0.0013 (4)	−0.0022 (4)
C16	0.0154 (5)	0.0197 (5)	0.0178 (5)	−0.0003 (4)	−0.0045 (4)	−0.0015 (4)

O1—C6	1.2301 (13)	C5—C6	1.5021 (15)
O2—C13	1.3550 (13)	C7—C8	1.4410 (16)
O2—H1O2	0.87 (2)	C7—H7A	0.9300
O3—C12	1.3626 (13)	C8—C9	1.3470 (16)
O3—C16	1.4352 (13)	C8—H8A	0.9300
N1—C2	1.3360 (16)	C9—C10	1.4598 (15)
N1—C3	1.3373 (16)	C9—H9A	0.9300
N2—C6	1.3494 (14)	C10—C15	1.4000 (15)
N2—N3	1.3856 (13)	C10—C11	1.4075 (15)
N2—H1N2	0.884 (17)	C11—C12	1.3808 (15)
N3—C7	1.2895 (15)	C11—H11A	0.9300
C1—C2	1.3862 (17)	C12—C13	1.4142 (15)
C1—C5	1.3875 (16)	C13—C14	1.3881 (15)
C1—H1A	0.9300	C14—C15	1.3904 (16)
C2—H2A	0.9300	C14—H14A	0.9300
C3—C4	1.3871 (17)	C15—H15A	0.9300
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.3889 (16)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C13—O2—H1O2	110.8 (13)	C9—C8—H8A	118.7
C12—O3—C16	117.55 (9)	C7—C8—H8A	118.7
C2—N1—C3	116.70 (10)	C8—C9—C10	126.10 (10)
C6—N2—N3	119.56 (9)	C8—C9—H9A	117.0
C6—N2—H1N2	121.8 (10)	C10—C9—H9A	117.0
N3—N2—H1N2	118.3 (10)	C15—C10—C11	118.52 (10)
C7—N3—N2	114.31 (9)	C15—C10—C9	120.18 (10)
C2—C1—C5	118.81 (11)	C11—C10—C9	121.29 (10)
C2—C1—H1A	120.6	C12—C11—C10	121.02 (10)
C5—C1—H1A	120.6	C12—C11—H11A	119.5
N1—C2—C1	123.79 (11)	C10—C11—H11A	119.5
N1—C2—H2A	118.1	O3—C12—C11	125.39 (10)
C1—C2—H2A	118.1	O3—C12—C13	114.57 (9)
N1—C3—C4	123.91 (11)	C11—C12—C13	120.04 (10)
N1—C3—H3A	118.0	O2—C13—C14	119.67 (10)
C4—C3—H3A	118.0	O2—C13—C12	121.34 (10)
C3—C4—C5	118.58 (11)	C14—C13—C12	118.99 (10)
C3—C4—H4A	120.7	C13—C14—C15	120.91 (10)
C5—C4—H4A	120.7	C13—C14—H14A	119.5
C1—C5—C4	118.19 (11)	C15—C14—H14A	119.5
C1—C5—C6	122.84 (10)	C14—C15—C10	120.51 (10)
C4—C5—C6	118.76 (10)	C14—C15—H15A	119.7
O1—C6—N2	124.21 (10)	C10—C15—H15A	119.7
O1—C6—C5	120.96 (10)	O3—C16—H16A	109.5
N2—C6—C5	114.79 (9)	O3—C16—H16B	109.5
N3—C7—C8	119.57 (10)	H16A—C16—H16B	109.5
N3—C7—H7A	120.2	O3—C16—H16C	109.5
C8—C7—H7A	120.2	H16A—C16—H16C	109.5
C9—C8—C7	122.51 (10)	H16B—C16—H16C	109.5
C6—N2—N3—C7	170.58 (10)	C8—C9—C10—C15	165.29 (12)
C3—N1—C2—C1	1.0 (2)	C8—C9—C10—C11	−15.62 (18)
C5—C1—C2—N1	0.6 (2)	C15—C10—C11—C12	−1.36 (16)
C2—N1—C3—C4	−1.61 (19)	C9—C10—C11—C12	179.53 (10)
N1—C3—C4—C5	0.7 (2)	C16—O3—C12—C11	−6.79 (15)
C2—C1—C5—C4	−1.55 (18)	C16—O3—C12—C13	172.87 (9)
C2—C1—C5—C6	173.17 (11)	C10—C11—C12—O3	−178.97 (10)
C3—C4—C5—C1	0.97 (18)	C10—C11—C12—C13	1.38 (16)
C3—C4—C5—C6	−173.96 (11)	O3—C12—C13—O2	−1.11 (15)
N3—N2—C6—O1	−1.93 (17)	C11—C12—C13—O2	178.58 (10)
N3—N2—C6—C5	−179.76 (9)	O3—C12—C13—C14	179.36 (10)
C1—C5—C6—O1	−144.63 (12)	C11—C12—C13—C14	−0.95 (16)
C4—C5—C6—O1	30.05 (16)	O2—C13—C14—C15	−179.00 (10)
C1—C5—C6—N2	33.28 (15)	C12—C13—C14—C15	0.54 (16)
C4—C5—C6—N2	−152.04 (11)	C13—C14—C15—C10	−0.54 (17)
N2—N3—C7—C8	176.04 (10)	C11—C10—C15—C14	0.93 (16)
N3—C7—C8—C9	176.67 (11)	C9—C10—C15—C14	−179.95 (10)
C7—C8—C9—C10	174.30 (11)

Cg1 is the centroid of the C10–C15 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.886 (15)	1.999 (15)	2.8622 (12)	164.4 (14)
O2—H1O2···N1ii	0.87 (2)	1.96 (2)	2.7750 (13)	156.9 (19)
C2—H2A···O3iii	0.93	2.55	3.1651 (14)	124
C4—H4A···N3iv	0.93	2.60	3.4747 (14)	156
C7—H7A···O1i	0.93	2.52	3.2405 (14)	135
C16—H16B···Cg1v	0.96	2.65	3.4556 (12)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.886 (15)	1.999 (15)	2.8622 (12)	164.4 (14)
O2—H1O2⋯N1ii	0.87 (2)	1.96 (2)	2.7750 (13)	156.9 (19)
C2—H2A⋯O3iii	0.93	2.55	3.1651 (14)	124
C4—H4A⋯N3iv	0.93	2.60	3.4747 (14)	156
C7—H7A⋯O1i	0.93	2.52	3.2405 (14)	135
C16—H16B⋯Cg1v	0.96	2.65	3.4556 (12)	142

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