(E)-N'-(3,4-Di-meth-oxy-benzyl-idene)nicotinohydrazide monohydrate.

In the title hydrated compound, C15H15N3O3·H2O, the nicotinohydrazide mol-ecule adopts a trans conformation with respect to the C=N double bond. The dihedral angle between the benzene and pyridine rings is 5.10 (14)°. In the crystal, the solvent water mol-ecule acts as an acceptor, forming an N-H⋯O hydrogen bond supported by two C-H⋯O contacts. It also acts as a donor, forming bifurcated O-H⋯(O,O) and O-H⋯N hydrogen bonds that combine with the former contacts to form zigzag chains of mol-ecules along the c-axis direction. An additional O-H⋯O donor contact completes a set of six hydrogen bonds to and from the water mol-ecule and connects it to a third nicotinohydrazide mol-ecule. This latter contact combines with weaker C-H⋯O hydrogen bonds supported by a C-H⋯π contact to stack mol-ecules along b in a three-dimensional network.

Related literature

For the biological activity of hydrazone compounds, see: Singh & Raghav (2011 ▶); Patil et al. (2011 ▶). For background to the use of nicotinohydrazides as catalysts and of their transition metal complexes in the treatment of tuberculosis, see: Torje et al. (2012 ▶). For closely related structures, see: Novina et al. (2013 ▶); Wang et al. (2010 ▶).

Experimental

Crystal data

C15H15N3O3·H2O

M = 303.32

Monoclinic,

a = 4.9128 (6) Å

b = 25.137 (4) Å

c = 12.2950 (16) Å

β = 96.513 (4)°

V = 1508.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.50 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.952, T max = 0.971

11633 measured reflections

3704 independent reflections

2250 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.141

S = 1.02

3704 reflections

209 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814013798/sj5412sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013798/sj5412Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013798/sj5412Isup3.cml

CCDC reference: 1008073

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H15N3O3·H2O	F(000) = 640
Mr = 303.32	Dx = 1.335 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2357 reflections
a = 4.9128 (6) Å	θ = 4.7–51.8°
b = 25.137 (4) Å	µ = 0.10 mm−1
c = 12.2950 (16) Å	T = 296 K
β = 96.513 (4)°	Block, colorless
V = 1508.6 (4) Å3	0.50 × 0.35 × 0.30 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3704 independent reflections
Radiation source: fine-focus sealed tube	2250 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω and φ scan	θmax = 28.3°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→6
Tmin = 0.952, Tmax = 0.971	k = −33→33
11633 measured reflections	l = −16→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0655P)2 + 0.1374P] where P = (Fo2 + 2Fc2)/3
3704 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.21 e Å−3
3 restraints	Δρmin = −0.23 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
C1	1.8728 (4)	0.00081 (9)	0.12935 (17)	0.0591 (6)
H1A	1.7449	−0.0075	0.0667	0.089*
H1B	1.9736	−0.0306	0.1531	0.089*
H1C	1.9975	0.0277	0.1101	0.089*
C2	1.5690 (3)	0.06393 (7)	0.19504 (13)	0.0345 (4)
C3	1.4107 (3)	0.07841 (7)	0.27937 (13)	0.0349 (4)
C4	1.2439 (3)	0.12194 (7)	0.26645 (13)	0.0360 (4)
H4	1.1402	0.1315	0.3221	0.043*
C5	1.2269 (3)	0.15227 (7)	0.17060 (13)	0.0343 (4)
C8	1.0486 (3)	0.19839 (7)	0.15615 (13)	0.0376 (4)
H8	1.0267	0.2158	0.0889	0.045*
C9	0.6145 (3)	0.27874 (7)	0.28846 (13)	0.0356 (4)
C10	0.4296 (3)	0.32458 (7)	0.25774 (13)	0.0358 (4)
C14	0.2785 (4)	0.34525 (9)	0.33488 (15)	0.0512 (5)
H14	0.2956	0.3293	0.4035	0.061*
C13	0.0882 (4)	0.40894 (9)	0.22029 (18)	0.0574 (6)
H13	−0.0306	0.4376	0.2065	0.069*
C12	0.2313 (5)	0.39213 (11)	0.13952 (19)	0.0764 (8)
H12	0.2132	0.4093	0.0721	0.092*
C11	0.4038 (5)	0.34939 (10)	0.15793 (17)	0.0704 (7)
H11	0.5030	0.3373	0.1028	0.084*
C6	1.3787 (3)	0.13702 (7)	0.08749 (13)	0.0396 (4)
H6	1.3658	0.1564	0.0227	0.047*
C7	1.5492 (3)	0.09318 (7)	0.10011 (13)	0.0388 (4)
H7	1.6511	0.0834	0.0440	0.047*
C15	1.2265 (4)	0.05011 (9)	0.43970 (15)	0.0578 (6)
H15A	1.2328	0.0847	0.4730	0.087*
H15C	1.2545	0.0234	0.4956	0.087*
H15B	1.0510	0.0449	0.3982	0.087*
N1	0.9212 (3)	0.21555 (6)	0.23409 (11)	0.0364 (3)
N2	0.7497 (3)	0.25839 (6)	0.20898 (10)	0.0370 (3)
H2N2	0.7300	0.2717	0.1441	0.044*
N3	0.1091 (4)	0.38654 (8)	0.31852 (15)	0.0637 (5)
O1	1.7281 (2)	0.01981 (5)	0.21562 (10)	0.0467 (3)
O1W	1.1763 (3)	0.21759 (7)	0.47728 (11)	0.0606 (4)
O2	1.4351 (3)	0.04615 (5)	0.36928 (10)	0.0496 (4)
O3	0.6430 (3)	0.26124 (6)	0.38267 (9)	0.0505 (4)
H1O1	1.310 (4)	0.2231 (12)	0.440 (2)	0.101 (10)*
H2O1	1.028 (4)	0.2235 (11)	0.4360 (19)	0.102 (10)*

	U11	U22	U33	U12	U13	U23
C1	0.0537 (11)	0.0579 (14)	0.0675 (14)	0.0190 (10)	0.0148 (10)	−0.0139 (11)
C2	0.0304 (8)	0.0321 (9)	0.0414 (9)	−0.0008 (7)	0.0062 (6)	−0.0027 (7)
C3	0.0366 (8)	0.0365 (10)	0.0318 (8)	−0.0006 (7)	0.0052 (6)	0.0023 (7)
C4	0.0401 (9)	0.0401 (10)	0.0291 (8)	0.0058 (8)	0.0094 (6)	−0.0026 (7)
C5	0.0368 (8)	0.0356 (10)	0.0307 (8)	0.0022 (7)	0.0038 (6)	−0.0009 (7)
C8	0.0437 (9)	0.0406 (10)	0.0287 (8)	0.0060 (8)	0.0049 (7)	0.0027 (7)
C9	0.0381 (9)	0.0392 (10)	0.0297 (8)	0.0015 (7)	0.0052 (6)	0.0002 (7)
C10	0.0360 (8)	0.0383 (10)	0.0335 (8)	0.0035 (7)	0.0060 (6)	−0.0004 (7)
C14	0.0625 (12)	0.0551 (13)	0.0375 (10)	0.0177 (10)	0.0117 (8)	0.0020 (9)
C13	0.0603 (12)	0.0493 (13)	0.0627 (13)	0.0206 (10)	0.0075 (10)	0.0025 (10)
C12	0.0972 (17)	0.0813 (18)	0.0549 (13)	0.0482 (15)	0.0267 (12)	0.0252 (12)
C11	0.0879 (16)	0.0809 (18)	0.0476 (12)	0.0467 (14)	0.0305 (11)	0.0188 (11)
C6	0.0448 (9)	0.0441 (11)	0.0310 (8)	0.0003 (8)	0.0094 (7)	0.0046 (8)
C7	0.0391 (9)	0.0432 (11)	0.0368 (9)	0.0017 (8)	0.0152 (7)	−0.0038 (8)
C15	0.0555 (12)	0.0773 (16)	0.0427 (10)	0.0078 (11)	0.0142 (9)	0.0198 (10)
N1	0.0409 (8)	0.0367 (9)	0.0313 (7)	0.0080 (6)	0.0023 (6)	0.0011 (6)
N2	0.0447 (8)	0.0388 (9)	0.0274 (7)	0.0107 (7)	0.0038 (6)	0.0049 (6)
N3	0.0736 (12)	0.0635 (13)	0.0565 (11)	0.0278 (10)	0.0180 (9)	−0.0034 (9)
O1	0.0467 (7)	0.0415 (8)	0.0543 (8)	0.0114 (6)	0.0159 (6)	0.0009 (6)
O1W	0.0661 (10)	0.0840 (12)	0.0303 (7)	−0.0146 (9)	−0.0007 (7)	0.0055 (7)
O2	0.0559 (8)	0.0533 (9)	0.0418 (7)	0.0151 (7)	0.0153 (6)	0.0152 (6)
O3	0.0611 (8)	0.0611 (9)	0.0305 (6)	0.0175 (7)	0.0106 (5)	0.0088 (6)

C1—O1	1.424 (2)	C14—N3	1.331 (2)
C1—H1A	0.9600	C14—H14	0.9300
C1—H1B	0.9600	C13—N3	1.326 (3)
C1—H1C	0.9600	C13—C12	1.348 (3)
C2—O1	1.364 (2)	C13—H13	0.9300
C2—C7	1.373 (2)	C12—C11	1.371 (3)
C2—C3	1.412 (2)	C12—H12	0.9300
C3—O2	1.3652 (19)	C11—H11	0.9300
C3—C4	1.366 (2)	C6—C7	1.382 (2)
C4—C5	1.398 (2)	C6—H6	0.9300
C4—H4	0.9300	C7—H7	0.9300
C5—C6	1.386 (2)	C15—O2	1.418 (2)
C5—C8	1.452 (2)	C15—H15A	0.9600
C8—N1	1.277 (2)	C15—H15C	0.9600
C8—H8	0.9300	C15—H15B	0.9600
C9—O3	1.2322 (19)	N1—N2	1.3806 (19)
C9—N2	1.344 (2)	N2—H2N2	0.8600
C9—C10	1.489 (2)	O1W—H1O1	0.856 (17)
C10—C11	1.370 (3)	O1W—H2O1	0.854 (17)
C10—C14	1.371 (2)
O1—C1—H1A	109.5	N3—C13—C12	123.02 (19)
O1—C1—H1B	109.5	N3—C13—H13	118.5
H1A—C1—H1B	109.5	C12—C13—H13	118.5
O1—C1—H1C	109.5	C13—C12—C11	119.2 (2)
H1A—C1—H1C	109.5	C13—C12—H12	120.4
H1B—C1—H1C	109.5	C11—C12—H12	120.4
O1—C2—C7	125.21 (15)	C10—C11—C12	119.83 (18)
O1—C2—C3	115.16 (15)	C10—C11—H11	120.1
C7—C2—C3	119.62 (15)	C12—C11—H11	120.1
O2—C3—C4	124.52 (14)	C7—C6—C5	120.51 (16)
O2—C3—C2	115.86 (15)	C7—C6—H6	119.7
C4—C3—C2	119.61 (15)	C5—C6—H6	119.7
C3—C4—C5	120.85 (15)	C2—C7—C6	120.38 (15)
C3—C4—H4	119.6	C2—C7—H7	119.8
C5—C4—H4	119.6	C6—C7—H7	119.8
C6—C5—C4	119.01 (16)	O2—C15—H15A	109.5
C6—C5—C8	119.90 (15)	O2—C15—H15C	109.5
C4—C5—C8	121.07 (14)	H15A—C15—H15C	109.5
N1—C8—C5	121.19 (15)	O2—C15—H15B	109.5
N1—C8—H8	119.4	H15A—C15—H15B	109.5
C5—C8—H8	119.4	H15C—C15—H15B	109.5
O3—C9—N2	122.34 (16)	C8—N1—N2	115.72 (14)
O3—C9—C10	121.05 (15)	C9—N2—N1	118.29 (13)
N2—C9—C10	116.61 (14)	C9—N2—H2N2	120.9
C11—C10—C14	116.41 (17)	N1—N2—H2N2	120.9
C11—C10—C9	124.86 (16)	C13—N3—C14	116.83 (17)
C14—C10—C9	118.70 (15)	C2—O1—C1	117.29 (15)
N3—C14—C10	124.68 (18)	H1O1—O1W—H2O1	108 (2)
N3—C14—H14	117.7	C3—O2—C15	116.70 (13)
C10—C14—H14	117.7
O1—C2—C3—O2	−0.8 (2)	C9—C10—C11—C12	−178.5 (2)
C7—C2—C3—O2	177.74 (15)	C13—C12—C11—C10	−0.3 (4)
O1—C2—C3—C4	−179.80 (15)	C4—C5—C6—C7	−1.4 (3)
C7—C2—C3—C4	−1.3 (2)	C8—C5—C6—C7	−179.96 (16)
O2—C3—C4—C5	−178.69 (15)	O1—C2—C7—C6	179.32 (15)
C2—C3—C4—C5	0.2 (3)	C3—C2—C7—C6	1.0 (3)
C3—C4—C5—C6	1.1 (3)	C5—C6—C7—C2	0.4 (3)
C3—C4—C5—C8	179.61 (15)	C5—C8—N1—N2	−177.58 (14)
C6—C5—C8—N1	−175.03 (16)	O3—C9—N2—N1	1.6 (3)
C4—C5—C8—N1	6.5 (3)	C10—C9—N2—N1	−179.42 (14)
O3—C9—C10—C11	174.1 (2)	C8—N1—N2—C9	−178.76 (15)
N2—C9—C10—C11	−4.9 (3)	C12—C13—N3—C14	−0.8 (4)
O3—C9—C10—C14	−3.7 (3)	C10—C14—N3—C13	−0.3 (3)
N2—C9—C10—C14	177.30 (17)	C7—C2—O1—C1	−3.9 (3)
C11—C10—C14—N3	1.0 (3)	C3—C2—O1—C1	174.54 (15)
C9—C10—C14—N3	178.98 (18)	C4—C3—O2—C15	16.5 (3)
N3—C13—C12—C11	1.1 (4)	C2—C3—O2—C15	−162.44 (16)
C14—C10—C11—C12	−0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N2···O1Wi	0.86	2.06	2.8942 (19)	165
O1W—H2O1···O3	0.85 (2)	2.15 (2)	2.955 (2)	157 (3)
O1W—H2O1···N1	0.85 (2)	2.49 (2)	3.1087 (19)	130 (2)
C11—H11···O1Wi	0.93	2.30	3.199 (3)	162
C8—H8···O1Wi	0.93	2.67	3.425 (2)	139
O1W—H1O1···O3ii	0.86 (2)	2.09 (2)	2.901 (2)	159 (3)
C1—H1C···Cg2ii	0.96	2.88	3.729 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N2⋯O1W i	0.86	2.06	2.8942 (19)	165
O1W—H2O1⋯O3	0.85 (2)	2.15 (2)	2.955 (2)	157 (3)
O1W—H2O1⋯N1	0.85 (2)	2.49 (2)	3.1087 (19)	130 (2)
C11—H11⋯O1W i	0.93	2.30	3.199 (3)	162
C8—H8⋯O1W i	0.93	2.67	3.425 (2)	139
O1W—H1O1⋯O3ii	0.86 (2)	2.09 (2)	2.901 (2)	159 (3)
C1—H1C⋯Cg2ii	0.96	2.88	3.729 (3)	148

Symmetry codes: (i) ; (ii) .