N'-[(Z)-4-Methyl-benzyl-idene]-4-nitro-benzohydrazide monohydrate.

In the title compound, C(15)H(13)N(3)O(3)·H(2)O, the two benzene rings form a dihedral angle of 2.03 (2)°. In the crystal structure, adjacent hydrazide mol-ecules are linked into dimers by water mol-ecules; these dimers are then stacked along the b axis. Inter-molecular O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds and a π-π stacking inter-action between the nitro-benzene and tolyl rings with a centroid-centroid distance of 3.8208 (3) Å are observed. There is also a short O⋯N contact [2.6824 (7) Å].

Related literature

For related literature on hydrazones, see: Sridhar & Perumal (2003 ▶). For the biological applications of hydrazides/hydrazones, see: Bedia et al. (2006 ▶). For a related structure, see: Fun et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H13N3O3·H2O

M = 301.30

Triclinic,

a = 6.5387 (1) Å

b = 6.9730 (1) Å

c = 15.9064 (3) Å

α = 80.524 (1)°

β = 82.628 (1)°

γ = 85.036 (1)°

V = 707.85 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100.0 (1) K

0.68 × 0.44 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.932, T max = 0.976

31311 measured reflections

7380 independent reflections

6571 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.118

S = 1.05

7380 reflections

211 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.59 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037008/is2358sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037008/is2358Isup2.hkl

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

C15H13N3O3·H2O	Z = 2
Mr = 301.30	F000 = 316
Triclinic, P1	Dx = 1.414 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.5387 (1) Å	Cell parameters from 9969 reflections
b = 6.9730 (1) Å	θ = 2.6–26.3º
c = 15.9064 (3) Å	µ = 0.11 mm−1
α = 80.524 (1)º	T = 100.0 (1) K
β = 82.628 (1)º	Block, colourless
γ = 85.036 (1)º	0.68 × 0.44 × 0.23 mm
V = 707.85 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	7380 independent reflections
Radiation source: fine-focus sealed tube	6571 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 100.0(1) K	θmax = 37.5º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.932, Tmax = 0.976	k = −11→10
31311 measured reflections	l = −27→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.1283P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
7380 reflections	Δρmax = 0.48 e Å−3
211 parameters	Δρmin = −0.59 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O1	1.27580 (6)	0.77076 (7)	−0.04714 (3)	0.01642 (8)
O2	0.75581 (8)	1.18850 (8)	−0.38841 (3)	0.02159 (10)
O3	0.46360 (8)	1.16591 (9)	−0.30724 (3)	0.02477 (11)
N1	1.08155 (7)	0.62939 (7)	0.10666 (3)	0.01228 (8)
N2	0.97488 (7)	0.71707 (7)	0.03900 (3)	0.01180 (8)
N3	0.65301 (8)	1.14188 (7)	−0.31919 (3)	0.01517 (9)
C1	1.25937 (9)	0.43357 (8)	0.25978 (3)	0.01394 (9)
H1A	1.3528	0.4556	0.2105	0.017*
C2	1.32689 (9)	0.33958 (9)	0.33630 (4)	0.01558 (9)
H2A	1.4660	0.2992	0.3375	0.019*
C3	1.19044 (10)	0.30421 (9)	0.41173 (4)	0.01618 (10)
C4	0.98236 (10)	0.36711 (9)	0.40850 (4)	0.01732 (10)
H4A	0.8891	0.3455	0.4579	0.021*
C5	0.91322 (9)	0.46166 (9)	0.33225 (4)	0.01511 (9)
H5A	0.7744	0.5032	0.3313	0.018*
C6	1.05015 (8)	0.49509 (8)	0.25695 (3)	0.01205 (8)
C7	0.96681 (8)	0.59124 (8)	0.17866 (3)	0.01265 (9)
H7A	0.8259	0.6261	0.1809	0.015*
C8	1.08418 (8)	0.78209 (7)	−0.03665 (3)	0.01124 (8)
C9	0.96283 (8)	0.87393 (7)	−0.10826 (3)	0.01078 (8)
C10	0.74981 (8)	0.92155 (8)	−0.09685 (3)	0.01259 (9)
H10A	0.6760	0.8932	−0.0428	0.015*
C11	0.64812 (8)	1.01101 (8)	−0.16601 (3)	0.01320 (9)
H11A	0.5067	1.0435	−0.1589	0.016*
C12	0.76204 (8)	1.05088 (8)	−0.24589 (3)	0.01220 (8)
C13	0.97361 (9)	1.00639 (8)	−0.25947 (3)	0.01340 (9)
H13A	1.0465	1.0355	−0.3137	0.016*
C14	1.07314 (8)	0.91711 (8)	−0.18969 (3)	0.01269 (9)
H14A	1.2148	0.8857	−0.1972	0.015*
C15	1.26554 (12)	0.20102 (11)	0.49388 (4)	0.02473 (13)
H15A	1.1517	0.1899	0.5386	0.037*
H15B	1.3687	0.2740	0.5096	0.037*
H15C	1.3242	0.0733	0.4859	0.037*
O1W	0.56488 (7)	0.60570 (7)	0.07749 (3)	0.01669 (8)
H1N2	0.8430 (12)	0.7058 (17)	0.0471 (8)	0.027 (3)*
H2W1	0.5907 (17)	0.4907 (12)	0.0684 (8)	0.031 (3)*
H1W1	0.4410 (13)	0.6364 (17)	0.0668 (8)	0.035 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.00972 (15)	0.0221 (2)	0.01583 (17)	0.00035 (13)	−0.00227 (13)	0.00155 (14)
O2	0.0250 (2)	0.0269 (2)	0.01076 (17)	−0.00148 (17)	−0.00275 (15)	0.00358 (15)
O3	0.01615 (19)	0.0361 (3)	0.0199 (2)	0.00133 (18)	−0.00737 (16)	0.00461 (19)
N1	0.01330 (18)	0.01250 (17)	0.01075 (17)	−0.00018 (13)	−0.00421 (13)	0.00081 (13)
N2	0.01085 (17)	0.01426 (18)	0.00977 (16)	−0.00046 (13)	−0.00339 (13)	0.00113 (13)
N3	0.0174 (2)	0.01585 (19)	0.01215 (18)	−0.00094 (15)	−0.00535 (15)	0.00083 (14)
C1	0.0137 (2)	0.0152 (2)	0.01227 (19)	−0.00081 (16)	−0.00285 (15)	0.00066 (15)
C2	0.0155 (2)	0.0166 (2)	0.0143 (2)	0.00085 (17)	−0.00481 (16)	−0.00018 (16)
C3	0.0208 (2)	0.0158 (2)	0.01158 (19)	0.00194 (17)	−0.00496 (17)	−0.00040 (16)
C4	0.0199 (2)	0.0196 (2)	0.01066 (19)	0.00142 (18)	−0.00093 (17)	0.00081 (16)
C5	0.0148 (2)	0.0174 (2)	0.01210 (19)	0.00041 (16)	−0.00163 (16)	−0.00002 (16)
C6	0.01369 (19)	0.01192 (19)	0.01037 (18)	−0.00115 (15)	−0.00323 (14)	0.00030 (14)
C7	0.01325 (19)	0.0133 (2)	0.01122 (18)	−0.00088 (15)	−0.00333 (15)	0.00004 (15)
C8	0.01101 (18)	0.01159 (18)	0.01084 (18)	0.00006 (14)	−0.00243 (14)	−0.00044 (14)
C9	0.01090 (18)	0.01125 (18)	0.00998 (17)	−0.00020 (14)	−0.00238 (14)	−0.00045 (14)
C10	0.01106 (18)	0.0154 (2)	0.01048 (18)	0.00026 (15)	−0.00182 (14)	0.00036 (15)
C11	0.01170 (19)	0.0154 (2)	0.01187 (19)	0.00029 (15)	−0.00297 (15)	0.00029 (15)
C12	0.01382 (19)	0.01256 (19)	0.01019 (18)	−0.00090 (15)	−0.00400 (15)	0.00040 (14)
C13	0.0141 (2)	0.0151 (2)	0.01041 (18)	−0.00143 (16)	−0.00148 (15)	−0.00005 (15)
C14	0.01159 (19)	0.0146 (2)	0.01130 (18)	−0.00053 (15)	−0.00128 (14)	−0.00060 (15)
C15	0.0321 (3)	0.0271 (3)	0.0134 (2)	0.0068 (2)	−0.0081 (2)	0.0011 (2)
O1W	0.01130 (16)	0.0212 (2)	0.01725 (18)	−0.00029 (13)	−0.00349 (13)	−0.00109 (14)

O1—C8	1.2400 (6)	C6—C7	1.4605 (7)
O2—N3	1.2246 (7)	C7—H7A	0.9300
O3—N3	1.2298 (7)	C8—C9	1.4970 (7)
N1—C7	1.2881 (7)	C9—C14	1.3994 (7)
N1—N2	1.3859 (6)	C9—C10	1.3994 (7)
N2—C8	1.3491 (7)	C10—C11	1.3898 (7)
N2—H1N2	0.864 (8)	C10—H10A	0.9300
N3—C12	1.4703 (7)	C11—C12	1.3867 (7)
C1—C2	1.3896 (8)	C11—H11A	0.9300
C1—C6	1.4019 (8)	C12—C13	1.3884 (8)
C1—H1A	0.9300	C13—C14	1.3895 (7)
C2—C3	1.4008 (8)	C13—H13A	0.9300
C2—H2A	0.9300	C14—H14A	0.9300
C3—C4	1.3977 (9)	C15—H15A	0.9600
C3—C15	1.5035 (8)	C15—H15B	0.9600
C4—C5	1.3913 (8)	C15—H15C	0.9600
C4—H4A	0.9300	O1W—H2W1	0.837 (8)
C5—C6	1.3999 (8)	O1W—H1W1	0.851 (8)
C5—H5A	0.9300
C7—N1—N2	114.21 (4)	O1—C8—N2	122.52 (5)
C8—N2—N1	118.48 (4)	O1—C8—C9	120.74 (5)
C8—N2—H1N2	125.4 (8)	N2—C8—C9	116.74 (4)
N1—N2—H1N2	115.2 (8)	C14—C9—C10	119.65 (5)
O2—N3—O3	123.96 (5)	C14—C9—C8	116.93 (4)
O2—N3—C12	118.18 (5)	C10—C9—C8	123.40 (5)
O3—N3—C12	117.85 (5)	C11—C10—C9	120.23 (5)
C2—C1—C6	119.91 (5)	C11—C10—H10A	119.9
C2—C1—H1A	120.0	C9—C10—H10A	119.9
C6—C1—H1A	120.0	C12—C11—C10	118.60 (5)
C1—C2—C3	121.56 (5)	C12—C11—H11A	120.7
C1—C2—H2A	119.2	C10—C11—H11A	120.7
C3—C2—H2A	119.2	C11—C12—C13	122.73 (5)
C4—C3—C2	118.18 (5)	C11—C12—N3	118.38 (5)
C4—C3—C15	120.88 (6)	C13—C12—N3	118.89 (5)
C2—C3—C15	120.95 (6)	C12—C13—C14	118.01 (5)
C5—C4—C3	120.72 (5)	C12—C13—H13A	121.0
C5—C4—H4A	119.6	C14—C13—H13A	121.0
C3—C4—H4A	119.6	C13—C14—C9	120.79 (5)
C4—C5—C6	120.80 (5)	C13—C14—H14A	119.6
C4—C5—H5A	119.6	C9—C14—H14A	119.6
C6—C5—H5A	119.6	C3—C15—H15A	109.5
C5—C6—C1	118.83 (5)	C3—C15—H15B	109.5
C5—C6—C7	118.05 (5)	H15A—C15—H15B	109.5
C1—C6—C7	123.11 (5)	C3—C15—H15C	109.5
N1—C7—C6	122.33 (5)	H15A—C15—H15C	109.5
N1—C7—H7A	118.8	H15B—C15—H15C	109.5
C6—C7—H7A	118.8	H2W1—O1W—H1W1	106.0 (10)
C7—N1—N2—C8	172.77 (5)	N2—C8—C9—C14	−171.45 (5)
C6—C1—C2—C3	−0.09 (9)	O1—C8—C9—C10	−168.59 (5)
C1—C2—C3—C4	−0.32 (9)	N2—C8—C9—C10	10.18 (8)
C1—C2—C3—C15	179.55 (6)	C14—C9—C10—C11	0.09 (8)
C2—C3—C4—C5	0.20 (9)	C8—C9—C10—C11	178.42 (5)
C15—C3—C4—C5	−179.67 (6)	C9—C10—C11—C12	0.20 (8)
C3—C4—C5—C6	0.33 (9)	C10—C11—C12—C13	−0.47 (8)
C4—C5—C6—C1	−0.73 (9)	C10—C11—C12—N3	178.76 (5)
C4—C5—C6—C7	178.66 (5)	O2—N3—C12—C11	175.31 (5)
C2—C1—C6—C5	0.61 (8)	O3—N3—C12—C11	−4.94 (8)
C2—C1—C6—C7	−178.75 (5)	O2—N3—C12—C13	−5.43 (8)
N2—N1—C7—C6	178.63 (5)	O3—N3—C12—C13	174.32 (6)
C5—C6—C7—N1	179.37 (5)	C11—C12—C13—C14	0.42 (8)
C1—C6—C7—N1	−1.26 (9)	N3—C12—C13—C14	−178.81 (5)
N1—N2—C8—O1	−1.88 (8)	C12—C13—C14—C9	−0.10 (8)
N1—N2—C8—C9	179.38 (4)	C10—C9—C14—C13	−0.14 (8)
O1—C8—C9—C14	9.78 (8)	C8—C9—C14—C13	−178.58 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1W	0.864 (8)	1.978 (9)	2.8191 (7)	164.4 (11)
O1W—H2W1···O1i	0.837 (9)	2.013 (9)	2.8327 (7)	166.1 (11)
O1W—H1W1···O1ii	0.851 (9)	2.258 (11)	2.9430 (6)	137.7 (10)
O1W—H1W1···N1ii	0.851 (9)	2.357 (9)	3.1287 (7)	151.0 (11)
C1—H1A···O1Wiii	0.93	2.50	3.4090 (7)	165
C4—H4A···O2iv	0.93	2.58	3.4565 (8)	157
C7—H7A···O1W	0.93	2.55	3.2393 (7)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1W	0.864 (8)	1.978 (9)	2.8191 (7)	164.4 (11)
O1W—H2W1⋯O1i	0.837 (9)	2.013 (9)	2.8327 (7)	166.1 (11)
O1W—H1W1⋯O1ii	0.851 (9)	2.258 (11)	2.9430 (6)	137.7 (10)
O1W—H1W1⋯N1ii	0.851 (9)	2.357 (9)	3.1287 (7)	151.0 (11)
C1—H1A⋯O1Wiii	0.93	2.50	3.4090 (7)	165
C4—H4A⋯O2iv	0.93	2.58	3.4565 (8)	157
C7—H7A⋯O1W	0.93	2.55	3.2393 (7)	132

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