(1E,1'E)-4,4'-[1,1'-(Hydrazine-1,2-diyl-idene)bis-(ethan-1-yl-1-yl-idene)]diphenol dihydrate.

The asymmetric unit of the title compound, C(16)H(16)N(2)O(2)·2H(2)O, contains one half-mol-ecule of diphenol and one water mol-ecule. The complete diphenol mol-ecule is generated by a crystallographic inversion centre. In the mol-ecule, the central C(meth-yl)-C=N-N=C-C(meth-yl) plane makes a dihedral angle of 8.88 (6)° with its adjacent benzene ring. In the crystal, the components are linked by O-H⋯N and O-H⋯O hydrogen bonds into a three-dimensional network. The crystal structure is further stabilized by a weak C-H⋯π inter-action.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Chantrapromma et al. (2010 ▶); Fun et al. (2010 ▶); Jansrisewangwong et al. (2010 ▶). For background to and the biological activity of hydro­zones, see: Bendre et al. (1998 ▶); El-Tabl et al. (2008 ▶); Kitaev et al. (1970 ▶); Qin et al. (2009 ▶); Ramamohan et al. (1995 ▶); Rollas & Küçükgüzel (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H16N2O2·2H2O

M = 304.34

Monoclinic,

a = 7.8522 (1) Å

b = 5.5151 (1) Å

c = 17.8918 (3) Å

β = 108.536 (1)°

V = 734.62 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.35 × 0.26 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.966, T max = 0.979

8010 measured reflections

2129 independent reflections

1903 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.125

S = 1.06

2129 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.34 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 datablock(s) global, I. DOI: 10.1107/S1600536811029679/is2750sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029679/is2750Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029679/is2750Isup3.cml

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

C16H16N2O2·2H2O	F(000) = 324
Mr = 304.34	Dx = 1.376 Mg m−3
Monoclinic, P21/c	Melting point = 377–379 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.8522 (1) Å	Cell parameters from 2129 reflections
b = 5.5151 (1) Å	θ = 2.4–30.0°
c = 17.8918 (3) Å	µ = 0.10 mm−1
β = 108.536 (1)°	T = 100 K
V = 734.62 (2) Å3	Block, yellow
Z = 2	0.35 × 0.26 × 0.22 mm

Bruker APEXII CCD area-detector diffractometer	2129 independent reflections
Radiation source: sealed tube	1903 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 30.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→11
Tmin = 0.966, Tmax = 0.979	k = −7→7
8010 measured reflections	l = −24→24

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.061P)2 + 0.4114P] where P = (Fo2 + 2Fc2)/3
2129 reflections	(Δ/σ)max = 0.001
101 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.34 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 120.0 (1) K.

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	0.97567 (10)	0.63439 (15)	0.90238 (4)	0.01443 (19)
H1O1	1.0145	0.4971	0.9166	0.022*
N1	0.55899 (11)	0.49760 (17)	0.53887 (5)	0.0144 (2)
C1	0.64270 (13)	0.65293 (19)	0.66844 (6)	0.0106 (2)
C2	0.63628 (14)	0.83658 (19)	0.72163 (6)	0.0131 (2)
H2A	0.5566	0.9650	0.7045	0.016*
C3	0.74735 (14)	0.82980 (19)	0.79977 (6)	0.0137 (2)
H3A	0.7421	0.9534	0.8343	0.016*
C4	0.86615 (13)	0.63756 (19)	0.82596 (6)	0.0111 (2)
C5	0.87307 (13)	0.45094 (19)	0.77420 (6)	0.0126 (2)
H5A	0.9515	0.3215	0.7918	0.015*
C6	0.76265 (13)	0.45958 (19)	0.69653 (6)	0.0123 (2)
H6A	0.7680	0.3350	0.6623	0.015*
C7	0.52532 (13)	0.65863 (19)	0.58524 (6)	0.0113 (2)
C8	0.37991 (14)	0.8466 (2)	0.56043 (6)	0.0160 (2)
H8A	0.4326	1.0054	0.5696	0.024*
H8B	0.2989	0.8269	0.5904	0.024*
H8C	0.3152	0.8278	0.5054	0.024*
O1W	0.07930 (12)	0.31062 (17)	0.45773 (6)	0.0252 (2)
H1W	0.0793	0.3113	0.5058	0.038*
H2W	0.1722	0.3860	0.4541	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0167 (4)	0.0153 (4)	0.0088 (3)	0.0003 (3)	0.0007 (3)	0.0002 (3)
N1	0.0136 (4)	0.0180 (5)	0.0093 (4)	0.0038 (3)	0.0002 (3)	−0.0019 (3)
C1	0.0106 (4)	0.0118 (5)	0.0093 (4)	−0.0001 (3)	0.0029 (3)	−0.0004 (3)
C2	0.0145 (4)	0.0122 (5)	0.0121 (4)	0.0025 (4)	0.0034 (4)	−0.0005 (3)
C3	0.0163 (5)	0.0125 (5)	0.0120 (4)	0.0007 (4)	0.0041 (4)	−0.0025 (3)
C4	0.0114 (4)	0.0131 (5)	0.0087 (4)	−0.0023 (3)	0.0030 (3)	−0.0001 (3)
C5	0.0132 (4)	0.0125 (5)	0.0116 (4)	0.0026 (3)	0.0033 (3)	0.0004 (3)
C6	0.0141 (4)	0.0121 (5)	0.0106 (4)	0.0013 (3)	0.0039 (3)	−0.0017 (3)
C7	0.0103 (4)	0.0131 (5)	0.0102 (4)	0.0005 (3)	0.0028 (3)	0.0006 (3)
C8	0.0164 (5)	0.0166 (5)	0.0128 (5)	0.0059 (4)	0.0016 (4)	−0.0010 (4)
O1W	0.0194 (4)	0.0227 (5)	0.0337 (5)	−0.0016 (3)	0.0089 (4)	0.0060 (4)

O1—C4	1.3644 (11)	C4—C5	1.3971 (14)
O1—H1O1	0.8256	C5—C6	1.3854 (13)
N1—C7	1.2985 (13)	C5—H5A	0.9300
N1—N1i	1.4050 (16)	C6—H6A	0.9300
C1—C2	1.4016 (14)	C7—C8	1.5010 (14)
C1—C6	1.4056 (14)	C8—H8A	0.9600
C1—C7	1.4814 (13)	C8—H8B	0.9600
C2—C3	1.3934 (13)	C8—H8C	0.9600
C2—H2A	0.9300	O1W—H1W	0.8598
C3—C4	1.3913 (14)	O1W—H2W	0.8601
C3—H3A	0.9300
C4—O1—H1O1	111.9	C6—C5—H5A	120.1
C7—N1—N1i	114.55 (10)	C4—C5—H5A	120.1
C2—C1—C6	118.04 (9)	C5—C6—C1	121.28 (9)
C2—C1—C7	121.45 (9)	C5—C6—H6A	119.4
C6—C1—C7	120.50 (9)	C1—C6—H6A	119.4
C3—C2—C1	121.04 (9)	N1—C7—C1	116.07 (9)
C3—C2—H2A	119.5	N1—C7—C8	125.01 (9)
C1—C2—H2A	119.5	C1—C7—C8	118.92 (9)
C4—C3—C2	119.82 (9)	C7—C8—H8A	109.5
C4—C3—H3A	120.1	C7—C8—H8B	109.5
C2—C3—H3A	120.1	H8A—C8—H8B	109.5
O1—C4—C3	119.26 (9)	C7—C8—H8C	109.5
O1—C4—C5	120.65 (9)	H8A—C8—H8C	109.5
C3—C4—C5	120.09 (9)	H8B—C8—H8C	109.5
C6—C5—C4	119.72 (9)	H1W—O1W—H2W	110.1
C6—C1—C2—C3	0.95 (16)	C2—C1—C6—C5	−0.70 (15)
C7—C1—C2—C3	−179.93 (9)	C7—C1—C6—C5	−179.83 (9)
C1—C2—C3—C4	−0.37 (16)	N1i—N1—C7—C1	177.76 (10)
C2—C3—C4—O1	179.26 (9)	N1i—N1—C7—C8	−2.78 (17)
C2—C3—C4—C5	−0.48 (16)	C2—C1—C7—N1	171.18 (10)
O1—C4—C5—C6	−179.01 (9)	C6—C1—C7—N1	−9.72 (14)
C3—C4—C5—C6	0.72 (15)	C2—C1—C7—C8	−8.31 (15)
C4—C5—C6—C1	−0.12 (16)	C6—C1—C7—C8	170.78 (10)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O1Wii	0.83	1.86	2.6747 (12)	171
O1W—H1W···O1iii	0.86	2.07	2.8429 (12)	149
O1W—H2W···N1i	0.86	2.17	3.0132 (14)	166
C5—H5A···Cg1iv	0.93	2.80	3.5046 (12)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O1Wi	0.83	1.86	2.6747 (12)	171
O1W—H1W⋯O1ii	0.86	2.07	2.8429 (12)	149
O1W—H2W⋯N1iii	0.86	2.17	3.0132 (14)	166
C5—H5A⋯Cg1iv	0.93	2.80	3.5046 (12)	134

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