(E)-N'-(2-Benzyl-oxybenzyl-idene)isonicotinohydrazide methanol solvate monohydrate.

The title compound, C(20)H(17)N(3)O(2)·CH(4)O·H(2)O, was synthesized by the condensation reaction of 2-benzyl-oxybenzaldehyde with isoniazid (isonicotinic acid hydrazide). The tricyclic compound displays a trans configuration with respect to the C=N double bond. The central benzene ring makes dihedral angles of 8.83 (7) and 70.39 (8)° with the pyridine ring and the terminal benzene ring, respectively. The dihedral angle between the pyridine ring and the terminal benzene ring is 73.11 (8)°. In the crystal structure, mol-ecules are connected by inter-molecular N-H⋯O, O-H⋯O, O-H⋯(N,N) and C-H⋯O hydrogen bonds, forming a two-dimensional network perpendicular to the a axis.

Related literature

For applications of isoniazid derivatives, see: Janin, 2007 ▶; Maccari et al. (2005 ▶); Slayden & Barry (2000 ▶). For the biological activity of Schiff bases, see: Kahwa et al. (1986 ▶). For related structures, see: Naveenkumar et al. (2010a ▶, 2010b ▶, 2010c ▶). For the synthesis of isoniazid derivatives, see: Lourenco et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H17N3O2·CH4O·H2O

M = 381.42

Monoclinic,

a = 17.763 (3) Å

b = 12.3888 (18) Å

c = 8.7450 (13) Å

β = 98.672 (3)°

V = 1902.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.35 × 0.18 × 0.09 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.968, T max = 0.992

24474 measured reflections

6515 independent reflections

4012 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.170

S = 1.00

6515 reflections

270 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.35 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/S1600536810016958/sj2796sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016958/sj2796Isup2.hkl

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

C20H17N3O2·CH4O·H2O	F(000) = 808
Mr = 381.42	Dx = 1.332 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3013 reflections
a = 17.763 (3) Å	θ = 2.3–30.0°
b = 12.3888 (18) Å	µ = 0.09 mm−1
c = 8.7450 (13) Å	T = 100 K
β = 98.672 (3)°	Plate, colourless
V = 1902.4 (5) Å3	0.35 × 0.18 × 0.09 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	6515 independent reflections
Radiation source: fine-focus sealed tube	4012 reflections with I > 2σ(I)
graphite	Rint = 0.069
φ and ω scans	θmax = 32.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→26
Tmin = 0.968, Tmax = 0.992	k = −17→18
24474 measured reflections	l = −13→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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0887P)2] where P = (Fo2 + 2Fc2)/3
6515 reflections	(Δ/σ)max < 0.001
270 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.35 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 s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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	0.12066 (6)	0.05407 (9)	0.36337 (14)	0.0250 (3)
O2	0.36364 (6)	0.37324 (8)	0.80611 (13)	0.0211 (2)
N1	−0.05513 (8)	0.28776 (12)	0.00600 (16)	0.0258 (3)
N2	0.17041 (7)	0.21885 (11)	0.43066 (15)	0.0194 (3)
N3	0.22141 (7)	0.17181 (10)	0.54646 (15)	0.0196 (3)
C1	0.04882 (9)	0.31412 (13)	0.2126 (2)	0.0241 (3)
H1A	0.0791	0.3622	0.2765	0.029*
C2	−0.00980 (9)	0.35168 (14)	0.1031 (2)	0.0270 (4)
H2A	−0.0181	0.4258	0.0966	0.032*
C3	−0.04163 (10)	0.18181 (14)	0.0186 (2)	0.0284 (4)
H3A	−0.0721	0.1356	−0.0480	0.034*
C4	0.01531 (9)	0.13683 (13)	0.1257 (2)	0.0256 (3)
H4A	0.0223	0.0624	0.1304	0.031*
C5	0.06174 (8)	0.20416 (12)	0.22571 (17)	0.0191 (3)
C6	0.12010 (8)	0.15226 (12)	0.34544 (18)	0.0194 (3)
C7	0.26917 (8)	0.23667 (12)	0.62477 (18)	0.0192 (3)
H7A	0.2676	0.3101	0.6022	0.023*
C8	0.32580 (8)	0.19465 (12)	0.74905 (17)	0.0176 (3)
C9	0.33274 (8)	0.08431 (12)	0.78078 (18)	0.0200 (3)
H9A	0.3004	0.0360	0.7218	0.024*
C10	0.38701 (9)	0.04540 (12)	0.89869 (19)	0.0216 (3)
H10A	0.3906	−0.0282	0.9193	0.026*
C11	0.43586 (8)	0.11734 (13)	0.98564 (19)	0.0216 (3)
H11A	0.4724	0.0914	1.0644	0.026*
C12	0.43089 (8)	0.22761 (12)	0.95664 (18)	0.0198 (3)
H12A	0.4644	0.2751	1.0145	0.024*
C13	0.37506 (8)	0.26656 (11)	0.83943 (17)	0.0179 (3)
C14	0.40996 (9)	0.45051 (12)	0.90037 (19)	0.0212 (3)
H14A	0.4624	0.4457	0.8825	0.025*
H14B	0.4084	0.4369	1.0091	0.025*
C15	0.37824 (9)	0.55991 (12)	0.85576 (17)	0.0201 (3)
C16	0.41662 (9)	0.63173 (13)	0.77156 (19)	0.0240 (3)
H16A	0.4638	0.6129	0.7455	0.029*
C17	0.38469 (10)	0.73098 (13)	0.7266 (2)	0.0291 (4)
H17A	0.4104	0.7784	0.6702	0.035*
C18	0.31456 (10)	0.75978 (13)	0.7654 (2)	0.0287 (4)
H18A	0.2932	0.8263	0.7349	0.034*
C19	0.27639 (10)	0.68912 (14)	0.8500 (2)	0.0278 (4)
H19A	0.2295	0.7086	0.8768	0.033*
C20	0.30781 (9)	0.58952 (13)	0.89466 (19)	0.0245 (3)
H20A	0.2818	0.5423	0.9508	0.029*
O3	0.17234 (7)	0.45730 (9)	0.42445 (15)	0.0268 (3)
C21	0.21264 (10)	0.52275 (14)	0.5437 (2)	0.0269 (3)
H21A	0.2657	0.5039	0.5583	0.040*
H21B	0.1926	0.5110	0.6383	0.040*
H21C	0.2068	0.5974	0.5149	0.040*
O1W	0.16524 (7)	0.56017 (11)	0.14832 (15)	0.0261 (3)
H1N2	0.1707 (11)	0.2913 (16)	0.416 (2)	0.027 (5)*
H1O3	0.1722 (13)	0.4936 (19)	0.339 (3)	0.051 (7)*
H1W1	0.1606 (14)	0.518 (2)	0.079 (3)	0.052 (7)*
H2W1	0.1375 (15)	0.616 (2)	0.115 (3)	0.056 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0287 (6)	0.0175 (5)	0.0262 (6)	−0.0017 (4)	−0.0046 (5)	0.0026 (5)
O2	0.0244 (5)	0.0139 (5)	0.0223 (5)	−0.0010 (4)	−0.0054 (4)	−0.0011 (4)
N1	0.0228 (6)	0.0274 (7)	0.0257 (7)	0.0022 (5)	−0.0009 (6)	0.0010 (6)
N2	0.0213 (6)	0.0161 (6)	0.0187 (6)	−0.0002 (5)	−0.0032 (5)	0.0025 (5)
N3	0.0188 (6)	0.0188 (6)	0.0199 (6)	0.0012 (4)	−0.0016 (5)	0.0024 (5)
C1	0.0232 (7)	0.0209 (7)	0.0259 (8)	−0.0017 (6)	−0.0038 (6)	−0.0008 (7)
C2	0.0259 (8)	0.0224 (8)	0.0309 (9)	0.0036 (6)	−0.0012 (7)	0.0024 (7)
C3	0.0274 (8)	0.0283 (9)	0.0259 (8)	−0.0019 (6)	−0.0078 (7)	−0.0013 (7)
C4	0.0275 (8)	0.0196 (8)	0.0269 (8)	−0.0007 (6)	−0.0045 (7)	−0.0009 (7)
C5	0.0181 (6)	0.0209 (7)	0.0179 (7)	−0.0005 (5)	0.0012 (6)	0.0020 (6)
C6	0.0203 (7)	0.0200 (7)	0.0173 (7)	−0.0019 (5)	0.0011 (6)	0.0000 (6)
C7	0.0207 (7)	0.0156 (7)	0.0202 (7)	−0.0008 (5)	−0.0008 (6)	0.0008 (6)
C8	0.0181 (6)	0.0165 (7)	0.0177 (7)	0.0006 (5)	0.0005 (5)	0.0012 (6)
C9	0.0205 (7)	0.0174 (7)	0.0213 (7)	−0.0007 (5)	0.0006 (6)	−0.0015 (6)
C10	0.0231 (7)	0.0163 (7)	0.0249 (8)	0.0022 (5)	0.0020 (6)	0.0035 (6)
C11	0.0195 (7)	0.0233 (8)	0.0208 (7)	0.0039 (5)	−0.0006 (6)	0.0025 (6)
C12	0.0178 (6)	0.0209 (7)	0.0195 (7)	0.0003 (5)	−0.0010 (6)	−0.0012 (6)
C13	0.0197 (6)	0.0152 (7)	0.0190 (7)	0.0011 (5)	0.0032 (6)	−0.0001 (6)
C14	0.0225 (7)	0.0170 (7)	0.0222 (7)	−0.0024 (5)	−0.0032 (6)	−0.0014 (6)
C15	0.0252 (7)	0.0170 (7)	0.0165 (7)	−0.0015 (5)	−0.0022 (6)	−0.0019 (6)
C16	0.0245 (7)	0.0228 (8)	0.0234 (8)	−0.0026 (6)	−0.0003 (6)	−0.0005 (7)
C17	0.0339 (9)	0.0220 (8)	0.0294 (9)	−0.0054 (6)	−0.0013 (7)	0.0039 (7)
C18	0.0361 (9)	0.0174 (8)	0.0294 (9)	0.0018 (6)	−0.0053 (8)	−0.0013 (7)
C19	0.0300 (8)	0.0251 (8)	0.0270 (8)	0.0051 (6)	0.0003 (7)	−0.0035 (7)
C20	0.0291 (8)	0.0222 (8)	0.0220 (8)	−0.0002 (6)	0.0032 (7)	−0.0003 (7)
O3	0.0307 (6)	0.0224 (6)	0.0244 (6)	−0.0056 (4)	−0.0052 (5)	0.0018 (5)
C21	0.0288 (8)	0.0243 (8)	0.0262 (8)	−0.0023 (6)	0.0000 (7)	−0.0033 (7)
O1W	0.0298 (6)	0.0224 (6)	0.0231 (6)	0.0033 (5)	−0.0058 (5)	−0.0012 (5)

O1—C6	1.2263 (18)	C11—C12	1.390 (2)
O2—C13	1.3619 (17)	C11—H11A	0.9300
O2—C14	1.4382 (18)	C12—C13	1.400 (2)
N1—C3	1.336 (2)	C12—H12A	0.9300
N1—C2	1.338 (2)	C14—C15	1.497 (2)
N2—C6	1.3542 (19)	C14—H14A	0.9700
N2—N3	1.3817 (18)	C14—H14B	0.9700
N2—H1N2	0.91 (2)	C15—C20	1.394 (2)
N3—C7	1.2881 (19)	C15—C16	1.397 (2)
C1—C5	1.383 (2)	C16—C17	1.386 (2)
C1—C2	1.385 (2)	C16—H16A	0.9300
C1—H1A	0.9300	C17—C18	1.386 (3)
C2—H2A	0.9300	C17—H17A	0.9300
C3—C4	1.387 (2)	C18—C19	1.387 (2)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.387 (2)	C19—C20	1.386 (2)
C4—H4A	0.9300	C19—H19A	0.9300
C5—C6	1.502 (2)	C20—H20A	0.9300
C7—C8	1.461 (2)	O3—C21	1.426 (2)
C7—H7A	0.9300	O3—H1O3	0.88 (2)
C8—C9	1.397 (2)	C21—H21A	0.9600
C8—C13	1.406 (2)	C21—H21B	0.9600
C9—C10	1.388 (2)	C21—H21C	0.9600
C9—H9A	0.9300	O1W—H1W1	0.80 (3)
C10—C11	1.388 (2)	O1W—H2W1	0.88 (3)
C10—H10A	0.9300
C13—O2—C14	117.99 (12)	C11—C12—C13	119.40 (14)
C3—N1—C2	116.47 (15)	C11—C12—H12A	120.3
C6—N2—N3	116.85 (13)	C13—C12—H12A	120.3
C6—N2—H1N2	123.0 (12)	O2—C13—C12	123.87 (14)
N3—N2—H1N2	120.1 (12)	O2—C13—C8	115.77 (13)
C7—N3—N2	115.66 (13)	C12—C13—C8	120.35 (13)
C5—C1—C2	119.11 (15)	O2—C14—C15	107.03 (12)
C5—C1—H1A	120.4	O2—C14—H14A	110.3
C2—C1—H1A	120.4	C15—C14—H14A	110.3
N1—C2—C1	123.90 (15)	O2—C14—H14B	110.3
N1—C2—H2A	118.0	C15—C14—H14B	110.3
C1—C2—H2A	118.0	H14A—C14—H14B	108.6
N1—C3—C4	123.64 (16)	C20—C15—C16	119.24 (14)
N1—C3—H3A	118.2	C20—C15—C14	119.41 (14)
C4—C3—H3A	118.2	C16—C15—C14	121.32 (14)
C5—C4—C3	119.19 (15)	C17—C16—C15	120.22 (15)
C5—C4—H4A	120.4	C17—C16—H16A	119.9
C3—C4—H4A	120.4	C15—C16—H16A	119.9
C1—C5—C4	117.68 (14)	C16—C17—C18	120.22 (16)
C1—C5—C6	124.60 (14)	C16—C17—H17A	119.9
C4—C5—C6	117.66 (14)	C18—C17—H17A	119.9
O1—C6—N2	122.82 (14)	C17—C18—C19	119.84 (15)
O1—C6—C5	120.34 (14)	C17—C18—H18A	120.1
N2—C6—C5	116.84 (13)	C19—C18—H18A	120.1
N3—C7—C8	119.84 (13)	C20—C19—C18	120.24 (16)
N3—C7—H7A	120.1	C20—C19—H19A	119.9
C8—C7—H7A	120.1	C18—C19—H19A	119.9
C9—C8—C13	118.68 (13)	C19—C20—C15	120.24 (15)
C9—C8—C7	121.79 (13)	C19—C20—H20A	119.9
C13—C8—C7	119.53 (13)	C15—C20—H20A	119.9
C10—C9—C8	121.22 (14)	C21—O3—H1O3	105.8 (16)
C10—C9—H9A	119.4	O3—C21—H21A	109.5
C8—C9—H9A	119.4	O3—C21—H21B	109.5
C9—C10—C11	119.40 (14)	H21A—C21—H21B	109.5
C9—C10—H10A	120.3	O3—C21—H21C	109.5
C11—C10—H10A	120.3	H21A—C21—H21C	109.5
C10—C11—C12	120.93 (14)	H21B—C21—H21C	109.5
C10—C11—H11A	119.5	H1W1—O1W—H2W1	107 (2)
C12—C11—H11A	119.5
C6—N2—N3—C7	179.30 (13)	C9—C10—C11—C12	0.3 (2)
C3—N1—C2—C1	0.1 (2)	C10—C11—C12—C13	0.9 (2)
C5—C1—C2—N1	−0.8 (3)	C14—O2—C13—C12	−2.2 (2)
C2—N1—C3—C4	0.5 (2)	C14—O2—C13—C8	176.90 (12)
N1—C3—C4—C5	−0.4 (3)	C11—C12—C13—O2	177.34 (13)
C2—C1—C5—C4	0.9 (2)	C11—C12—C13—C8	−1.7 (2)
C2—C1—C5—C6	−176.15 (14)	C9—C8—C13—O2	−177.83 (12)
C3—C4—C5—C1	−0.3 (2)	C7—C8—C13—O2	2.38 (19)
C3—C4—C5—C6	176.90 (14)	C9—C8—C13—C12	1.3 (2)
N3—N2—C6—O1	−3.1 (2)	C7—C8—C13—C12	−178.47 (13)
N3—N2—C6—C5	176.55 (12)	C13—O2—C14—C15	−171.52 (12)
C1—C5—C6—O1	169.54 (15)	O2—C14—C15—C20	69.93 (18)
C4—C5—C6—O1	−7.5 (2)	O2—C14—C15—C16	−107.99 (16)
C1—C5—C6—N2	−10.1 (2)	C20—C15—C16—C17	−0.4 (2)
C4—C5—C6—N2	172.90 (14)	C14—C15—C16—C17	177.56 (15)
N2—N3—C7—C8	−179.56 (12)	C15—C16—C17—C18	0.2 (3)
N3—C7—C8—C9	3.6 (2)	C16—C17—C18—C19	0.2 (3)
N3—C7—C8—C13	−176.60 (13)	C17—C18—C19—C20	−0.5 (3)
C13—C8—C9—C10	−0.1 (2)	C18—C19—C20—C15	0.4 (3)
C7—C8—C9—C10	179.69 (14)	C16—C15—C20—C19	0.1 (2)
C8—C9—C10—C11	−0.7 (2)	C14—C15—C20—C19	−177.91 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O3	0.91 (2)	2.06 (2)	2.9549 (18)	169.9 (16)
O3—H1O3···O1W	0.87 (3)	1.85 (3)	2.7165 (19)	174 (3)
O1W—H1W1···O1i	0.80 (3)	2.11 (3)	2.8713 (18)	160 (2)
O1W—H1W1···N3i	0.80 (3)	2.62 (3)	3.2119 (19)	133 (2)
O1W—H2W1···N1ii	0.87 (3)	2.05 (3)	2.898 (2)	163 (2)
C1—H1A···O3	0.93	2.27	3.189 (2)	169
C2—H2A···O1iii	0.93	2.48	3.229 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O3	0.91 (2)	2.06 (2)	2.9549 (18)	169.9 (16)
O3—H1O3⋯O1W	0.87 (3)	1.85 (3)	2.7165 (19)	174 (3)
O1W—H1W1⋯O1i	0.80 (3)	2.11 (3)	2.8713 (18)	160 (2)
O1W—H1W1⋯N3i	0.80 (3)	2.62 (3)	3.2119 (19)	133 (2)
O1W—H2W1⋯N1ii	0.87 (3)	2.05 (3)	2.898 (2)	163 (2)
C1—H1A⋯O3	0.93	2.27	3.189 (2)	169
C2—H2A⋯O1iii	0.93	2.48	3.229 (2)	137

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