(E)-N'-(3-Benz-yloxy-4-methoxy-benzyl-idene)isonicotinohydrazide.

In the title compound, C(21)H(19)N(3)O(3), the pyridine ring forms a dihedral angle of 15.25 (6)° with the benzene ring. The dihedral angle between the two benzene rings is 83.66 (7)°. The meth-oxy group is slightly twisted away from the attached ring [C-O-C-C = 7.5 (2)°]. In the crystal structure, mol-ecules are linked into a three-dimensional network by inter-molecular N-H⋯N and C-H⋯O hydrogen bonds. The structure is further 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: Lourenço et al. (2008 ▶). For the biological activity of Schiff bases, see: Kahwa et al. (1986 ▶). For related structures, see: Naveenkumar, Sadikun, Ibrahim, Goh & Fun (2009 ▶); Naveenkumar, Sadikun, Ibrahim, Yeap & Fun (2009 ▶); Shi (2005 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H19N3O3

M = 361.39

Monoclinic,

a = 18.3930 (6) Å

b = 11.5574 (4) Å

c = 8.3508 (3) Å

β = 93.436 (2)°

V = 1771.98 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.71 × 0.13 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.937, T max = 0.992

27863 measured reflections

6434 independent reflections

3841 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.145

S = 1.06

6433 reflections

249 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.28 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/S1600536809037921/ci2917sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037921/ci2917Isup2.hkl

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

C21H19N3O3	F(000) = 760
Mr = 361.39	Dx = 1.355 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4601 reflections
a = 18.3930 (6) Å	θ = 2.8–32.1°
b = 11.5574 (4) Å	µ = 0.09 mm−1
c = 8.3508 (3) Å	T = 100 K
β = 93.436 (2)°	Needle, yellow
V = 1771.98 (11) Å3	0.71 × 0.13 × 0.09 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6434 independent reflections
Radiation source: fine-focus sealed tube	3841 reflections with I > 2σ(I)
graphite	Rint = 0.061
φ and ω scans	θmax = 32.6°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −26→27
Tmin = 0.937, Tmax = 0.992	k = −15→17
27863 measured reflections	l = −12→12

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0618P)2] where P = (Fo2 + 2Fc2)/3
6433 reflections	(Δ/σ)max = 0.001
249 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.28 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 > 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
O1	0.34254 (5)	0.51645 (9)	0.11366 (12)	0.0270 (2)
O2	0.17576 (5)	0.99561 (8)	0.38579 (11)	0.0206 (2)
O3	0.17536 (5)	1.19805 (8)	0.25594 (11)	0.0221 (2)
N1	0.49029 (7)	0.30387 (11)	−0.27715 (14)	0.0258 (3)
N2	0.38144 (6)	0.66534 (10)	−0.03723 (14)	0.0205 (3)
N3	0.34440 (6)	0.74619 (10)	0.04977 (13)	0.0205 (3)
C1	0.46166 (7)	0.50212 (12)	−0.22030 (17)	0.0228 (3)
H1A	0.4687	0.5799	−0.2432	0.027*
C2	0.49753 (8)	0.41733 (13)	−0.30194 (17)	0.0239 (3)
H2A	0.5287	0.4409	−0.3792	0.029*
C3	0.44347 (8)	0.27391 (13)	−0.16720 (19)	0.0310 (4)
H3A	0.4361	0.1955	−0.1492	0.037*
C4	0.40545 (8)	0.35211 (13)	−0.07883 (18)	0.0265 (3)
H4A	0.3738	0.3263	−0.0037	0.032*
C5	0.41511 (7)	0.46942 (12)	−0.10385 (15)	0.0182 (3)
C6	0.37626 (7)	0.55180 (12)	0.00140 (16)	0.0190 (3)
C7	0.33453 (7)	0.84479 (12)	−0.02067 (16)	0.0192 (3)
H7A	0.3528	0.8565	−0.1209	0.023*
C8	0.29549 (7)	0.93788 (12)	0.05350 (16)	0.0185 (3)
C9	0.29436 (7)	1.04692 (12)	−0.01554 (16)	0.0205 (3)
H9A	0.3198	1.0602	−0.1068	0.025*
C10	0.25541 (7)	1.13699 (12)	0.05066 (16)	0.0211 (3)
H10A	0.2556	1.2102	0.0044	0.025*
C11	0.21677 (7)	1.11759 (11)	0.18421 (16)	0.0182 (3)
C12	0.21699 (7)	1.00623 (11)	0.25633 (15)	0.0173 (3)
C13	0.25588 (7)	0.91782 (12)	0.18985 (16)	0.0186 (3)
H13A	0.2559	0.8445	0.2356	0.022*
C14	0.16762 (8)	0.88010 (12)	0.44760 (18)	0.0246 (3)
H14A	0.2148	0.8492	0.4839	0.030*
H14B	0.1466	0.8299	0.3641	0.030*
C15	0.11900 (7)	0.88528 (11)	0.58412 (17)	0.0197 (3)
C16	0.14817 (8)	0.90316 (12)	0.73981 (18)	0.0255 (3)
H16A	0.1983	0.9111	0.7585	0.031*
C17	0.10355 (9)	0.90916 (13)	0.86672 (18)	0.0312 (4)
H17A	0.1236	0.9215	0.9702	0.037*
C18	0.02901 (9)	0.89689 (13)	0.83993 (19)	0.0312 (4)
H18A	−0.0011	0.9007	0.9254	0.037*
C19	−0.00072 (8)	0.87894 (13)	0.6859 (2)	0.0318 (4)
H19A	−0.0508	0.8707	0.6677	0.038*
C20	0.04401 (8)	0.87320 (13)	0.55915 (18)	0.0260 (3)
H20A	0.0237	0.8611	0.4558	0.031*
C21	0.16494 (9)	1.30698 (12)	0.17427 (18)	0.0280 (3)
H21A	0.1321	1.3542	0.2310	0.042*
H21B	0.1449	1.2936	0.0671	0.042*
H21C	0.2109	1.3459	0.1703	0.042*
H1N2	0.4037 (9)	0.6892 (16)	−0.122 (2)	0.046 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0320 (5)	0.0276 (6)	0.0229 (5)	0.0005 (5)	0.0133 (5)	0.0027 (4)
O2	0.0252 (5)	0.0174 (5)	0.0203 (5)	0.0004 (4)	0.0108 (4)	0.0016 (4)
O3	0.0297 (5)	0.0164 (5)	0.0210 (5)	0.0043 (4)	0.0079 (4)	0.0011 (4)
N1	0.0284 (6)	0.0237 (6)	0.0258 (6)	0.0024 (5)	0.0045 (5)	−0.0026 (5)
N2	0.0244 (6)	0.0200 (6)	0.0179 (6)	0.0025 (5)	0.0094 (5)	−0.0010 (5)
N3	0.0211 (6)	0.0210 (6)	0.0201 (6)	0.0020 (5)	0.0076 (5)	−0.0033 (5)
C1	0.0271 (7)	0.0185 (7)	0.0236 (7)	0.0026 (6)	0.0083 (6)	0.0020 (6)
C2	0.0248 (7)	0.0265 (8)	0.0212 (7)	0.0042 (6)	0.0084 (6)	0.0012 (6)
C3	0.0362 (8)	0.0188 (7)	0.0390 (9)	−0.0011 (7)	0.0123 (7)	0.0000 (6)
C4	0.0271 (7)	0.0220 (7)	0.0315 (8)	0.0000 (6)	0.0113 (6)	0.0032 (6)
C5	0.0181 (6)	0.0211 (7)	0.0156 (6)	0.0020 (5)	0.0036 (5)	0.0004 (5)
C6	0.0187 (6)	0.0204 (7)	0.0183 (7)	0.0007 (5)	0.0038 (5)	0.0006 (5)
C7	0.0183 (6)	0.0223 (7)	0.0178 (6)	−0.0007 (5)	0.0062 (5)	−0.0009 (5)
C8	0.0171 (6)	0.0206 (7)	0.0180 (6)	−0.0010 (5)	0.0034 (5)	−0.0020 (5)
C9	0.0217 (7)	0.0224 (7)	0.0180 (7)	−0.0013 (6)	0.0060 (5)	0.0009 (5)
C10	0.0247 (7)	0.0182 (7)	0.0207 (7)	−0.0007 (6)	0.0034 (6)	0.0023 (5)
C11	0.0200 (6)	0.0174 (6)	0.0175 (6)	0.0003 (5)	0.0027 (5)	−0.0021 (5)
C12	0.0172 (6)	0.0187 (6)	0.0163 (6)	−0.0020 (5)	0.0049 (5)	−0.0011 (5)
C13	0.0193 (6)	0.0178 (6)	0.0190 (7)	−0.0001 (5)	0.0043 (5)	0.0011 (5)
C14	0.0287 (7)	0.0166 (7)	0.0301 (8)	0.0018 (6)	0.0139 (6)	0.0041 (6)
C15	0.0236 (7)	0.0142 (6)	0.0221 (7)	0.0016 (5)	0.0084 (6)	0.0016 (5)
C16	0.0274 (7)	0.0196 (7)	0.0294 (8)	−0.0022 (6)	−0.0005 (6)	0.0015 (6)
C17	0.0507 (10)	0.0242 (8)	0.0188 (7)	0.0000 (7)	0.0031 (7)	−0.0011 (6)
C18	0.0440 (9)	0.0239 (8)	0.0280 (8)	0.0008 (7)	0.0208 (7)	0.0000 (6)
C19	0.0238 (7)	0.0328 (9)	0.0401 (10)	−0.0015 (6)	0.0126 (7)	−0.0020 (7)
C20	0.0251 (7)	0.0315 (8)	0.0217 (7)	0.0011 (6)	0.0048 (6)	−0.0015 (6)
C21	0.0405 (9)	0.0181 (7)	0.0260 (8)	0.0074 (6)	0.0074 (7)	0.0032 (6)

O1—C6	1.2249 (16)	C9—C10	1.3964 (19)
O2—C12	1.3628 (16)	C9—H9A	0.93
O2—C14	1.4423 (16)	C10—C11	1.3763 (19)
O3—C11	1.3633 (16)	C10—H10A	0.93
O3—C21	1.4391 (16)	C11—C12	1.4208 (18)
N1—C2	1.3354 (19)	C12—C13	1.3826 (18)
N1—C3	1.3414 (19)	C13—H13A	0.93
N2—C6	1.3560 (18)	C14—C15	1.492 (2)
N2—N3	1.3871 (16)	C14—H14A	0.97
N2—H1N2	0.885 (18)	C14—H14B	0.97
N3—C7	1.2902 (17)	C15—C20	1.390 (2)
C1—C2	1.3836 (19)	C15—C16	1.392 (2)
C1—C5	1.3861 (19)	C16—C17	1.380 (2)
C1—H1A	0.93	C16—H16A	0.93
C2—H2A	0.93	C17—C18	1.383 (2)
C3—C4	1.383 (2)	C17—H17A	0.93
C3—H3A	0.93	C18—C19	1.383 (2)
C4—C5	1.3849 (19)	C18—H18A	0.93
C4—H4A	0.93	C19—C20	1.380 (2)
C5—C6	1.5049 (19)	C19—H19A	0.93
C7—C8	1.4527 (19)	C20—H20A	0.93
C7—H7A	0.93	C21—H21A	0.96
C8—C9	1.3855 (19)	C21—H21B	0.96
C8—C13	1.4072 (18)	C21—H21C	0.96
C12—O2—C14	116.22 (10)	O3—C11—C12	114.78 (11)
C11—O3—C21	116.78 (10)	C10—C11—C12	120.17 (12)
C2—N1—C3	115.70 (13)	O2—C12—C13	125.30 (12)
C6—N2—N3	118.92 (12)	O2—C12—C11	115.49 (11)
C6—N2—H1N2	122.3 (12)	C13—C12—C11	119.18 (12)
N3—N2—H1N2	118.4 (12)	C12—C13—C8	120.56 (12)
C7—N3—N2	114.60 (11)	C12—C13—H13A	119.7
C2—C1—C5	119.03 (13)	C8—C13—H13A	119.7
C2—C1—H1A	120.5	O2—C14—C15	108.43 (11)
C5—C1—H1A	120.5	O2—C14—H14A	110.0
N1—C2—C1	124.35 (14)	C15—C14—H14A	110.0
N1—C2—H2A	117.8	O2—C14—H14B	110.0
C1—C2—H2A	117.8	C15—C14—H14B	110.0
N1—C3—C4	124.23 (14)	H14A—C14—H14B	108.4
N1—C3—H3A	117.9	C20—C15—C16	118.60 (13)
C4—C3—H3A	117.9	C20—C15—C14	121.09 (13)
C3—C4—C5	119.06 (14)	C16—C15—C14	120.30 (13)
C3—C4—H4A	120.5	C17—C16—C15	120.72 (14)
C5—C4—H4A	120.5	C17—C16—H16A	119.6
C4—C5—C1	117.58 (13)	C15—C16—H16A	119.6
C4—C5—C6	117.49 (12)	C16—C17—C18	119.99 (14)
C1—C5—C6	124.89 (13)	C16—C17—H17A	120.0
O1—C6—N2	123.42 (13)	C18—C17—H17A	120.0
O1—C6—C5	121.06 (13)	C19—C18—C17	119.91 (15)
N2—C6—C5	115.52 (12)	C19—C18—H18A	120.0
N3—C7—C8	121.29 (12)	C17—C18—H18A	120.0
N3—C7—H7A	119.4	C20—C19—C18	119.98 (14)
C8—C7—H7A	119.4	C20—C19—H19A	120.0
C9—C8—C13	119.41 (12)	C18—C19—H19A	120.0
C9—C8—C7	119.45 (12)	C19—C20—C15	120.79 (14)
C13—C8—C7	121.07 (12)	C19—C20—H20A	119.6
C8—C9—C10	120.56 (13)	C15—C20—H20A	119.6
C8—C9—H9A	119.7	O3—C21—H21A	109.5
C10—C9—H9A	119.7	O3—C21—H21B	109.5
C11—C10—C9	120.10 (13)	H21A—C21—H21B	109.5
C11—C10—H10A	120.0	O3—C21—H21C	109.5
C9—C10—H10A	120.0	H21A—C21—H21C	109.5
O3—C11—C10	125.04 (12)	H21B—C21—H21C	109.5
C6—N2—N3—C7	−160.87 (12)	C9—C10—C11—O3	−178.10 (12)
C3—N1—C2—C1	1.4 (2)	C9—C10—C11—C12	0.70 (19)
C5—C1—C2—N1	0.4 (2)	C14—O2—C12—C13	−5.78 (18)
C2—N1—C3—C4	−1.8 (2)	C14—O2—C12—C11	172.17 (11)
N1—C3—C4—C5	0.3 (2)	O3—C11—C12—O2	0.27 (16)
C3—C4—C5—C1	1.5 (2)	C10—C11—C12—O2	−178.65 (11)
C3—C4—C5—C6	−176.45 (12)	O3—C11—C12—C13	178.35 (11)
C2—C1—C5—C4	−1.84 (19)	C10—C11—C12—C13	−0.56 (19)
C2—C1—C5—C6	175.95 (12)	O2—C12—C13—C8	178.59 (12)
N3—N2—C6—O1	−2.77 (19)	C11—C12—C13—C8	0.71 (18)
N3—N2—C6—C5	177.17 (10)	C9—C8—C13—C12	−0.98 (19)
C4—C5—C6—O1	6.12 (19)	C7—C8—C13—C12	−177.89 (12)
C1—C5—C6—O1	−171.67 (13)	C12—O2—C14—C15	−178.00 (10)
C4—C5—C6—N2	−173.82 (12)	O2—C14—C15—C20	89.96 (15)
C1—C5—C6—N2	8.39 (18)	O2—C14—C15—C16	−89.64 (15)
N2—N3—C7—C8	178.85 (11)	C20—C15—C16—C17	−0.2 (2)
N3—C7—C8—C9	171.47 (12)	C14—C15—C16—C17	179.39 (13)
N3—C7—C8—C13	−11.63 (19)	C15—C16—C17—C18	0.3 (2)
C13—C8—C9—C10	1.11 (19)	C16—C17—C18—C19	−0.2 (2)
C7—C8—C9—C10	178.06 (12)	C17—C18—C19—C20	0.1 (2)
C8—C9—C10—C11	−0.98 (19)	C18—C19—C20—C15	0.0 (2)
C21—O3—C11—C10	7.50 (19)	C16—C15—C20—C19	0.1 (2)
C21—O3—C11—C12	−171.35 (11)	C14—C15—C20—C19	−179.52 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N1i	0.88 (2)	2.54 (2)	3.3122 (17)	146 (1)
C9—H9A···O1ii	0.93	2.55	3.3524 (17)	144
C19—H19A···O3iii	0.93	2.54	3.3960 (17)	153
C17—H17A···Cg1iv	0.93	2.93	3.6694 (17)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1i	0.88 (2)	2.54 (2)	3.3122 (17)	146 (1)
C9—H9A⋯O1ii	0.93	2.55	3.3524 (17)	144
C19—H19A⋯O3iii	0.93	2.54	3.3960 (17)	153
C17—H17A⋯Cg1iv	0.93	2.93	3.6694 (17)	137

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