(E)-N'-(4-Eth-oxy-benzyl-idene)-4-hy-droxy-benzohydrazide dihydrate.

The benzohydrazide mol-ecule of the title compound, C(16)H(16)N(2)O(3)·2H(2)O, exists in a trans conformation with respect to the C=N double bond. The central O=C-NH-N=C plane [r.m.s. deviation of 0.0165 (1) Å for the five non-H atoms] makes dihedral angles of 6.04 (8) and 2.38 (8)°, respectively, with the hy-droxy- and eth-oxy-substituted benzene rings. The dihedral angle between these benzene rings is 3.82 (7)°. The eth-oxy group is almost coplanar with the attached benzene ring with a C-O-C-C torsion angle of -176.58 (11)°. In the crystal, the benzohydrazide and water mol-ecules are linked by N-H⋯O, O-H⋯O , O-H⋯N and C-H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶, 2012 ▶). For applications of benzohydrazides, see: Loncle et al. (2004 ▶); Molyneux (2004 ▶); Promdet et al. (2011 ▶); Raj et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H16N2O3·2H2O

M = 320.34

Monoclinic,

a = 7.1655 (1) Å

b = 17.3895 (3) Å

c = 13.6202 (2) Å

β = 110.875 (1)°

V = 1585.74 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.29 × 0.16 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.971, T max = 0.984

22228 measured reflections

5737 independent reflections

4310 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.155

S = 1.03

5737 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.73 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 datablock(s) global, I. DOI: 10.1107/S1600536812019356/is5130sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019356/is5130Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019356/is5130Isup3.cml

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

C16H16N2O3·2H2O	F(000) = 680
Mr = 320.34	Dx = 1.342 Mg m−3
Monoclinic, P21/c	Melting point = 373–374 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.1655 (1) Å	Cell parameters from 5737 reflections
b = 17.3895 (3) Å	θ = 2.0–32.5°
c = 13.6202 (2) Å	µ = 0.10 mm−1
β = 110.875 (1)°	T = 100 K
V = 1585.74 (4) Å3	Block, colorless
Z = 4	0.29 × 0.16 × 0.16 mm

Bruker APEXII CCD area-detector diffractometer	5737 independent reflections
Radiation source: sealed tube	4310 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 32.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.971, Tmax = 0.984	k = −26→19
22228 measured reflections	l = −20→18

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0735P)2 + 0.7894P] where P = (Fo2 + 2Fc2)/3
5737 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.28 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 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 > 2sigma(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	0.75546 (15)	0.81977 (6)	0.40609 (8)	0.0174 (2)
O2	0.60182 (15)	0.81464 (6)	−0.08291 (8)	0.0188 (2)
H1	0.6435	0.7704	−0.0894	0.028*
O3	0.85596 (15)	1.15548 (6)	0.90045 (8)	0.0198 (2)
N1	0.70782 (16)	0.94655 (7)	0.37373 (9)	0.0146 (2)
H2	0.6729	0.9842	0.3315	0.018*
N2	0.75068 (16)	0.96088 (7)	0.47938 (9)	0.0151 (2)
C1	0.67580 (17)	0.86049 (7)	0.22842 (10)	0.0130 (2)
C2	0.67471 (19)	0.78444 (8)	0.19463 (11)	0.0156 (2)
H2A	0.6925	0.7437	0.2436	0.019*
C3	0.64817 (19)	0.76747 (8)	0.09099 (11)	0.0162 (2)
H3A	0.6461	0.7155	0.0690	0.019*
C4	0.62471 (18)	0.82718 (8)	0.01968 (10)	0.0145 (2)
C5	0.62192 (19)	0.90311 (8)	0.05149 (11)	0.0163 (2)
H5A	0.6018	0.9436	0.0020	0.020*
C6	0.64847 (19)	0.91980 (8)	0.15534 (11)	0.0156 (2)
H6A	0.6481	0.9718	0.1768	0.019*
C7	0.71456 (17)	0.87382 (7)	0.34201 (10)	0.0127 (2)
C8	0.73020 (19)	1.03161 (8)	0.50069 (11)	0.0162 (2)
H8A	0.6885	1.0676	0.4446	0.019*
C9	0.76804 (19)	1.05918 (8)	0.60712 (11)	0.0155 (2)
C10	0.8108 (2)	1.01088 (8)	0.69423 (11)	0.0200 (3)
H10A	0.8197	0.9569	0.6858	0.024*
C11	0.8404 (2)	1.04100 (8)	0.79300 (11)	0.0201 (3)
H11A	0.8681	1.0077	0.8517	0.024*
C12	0.82933 (18)	1.12032 (8)	0.80608 (11)	0.0166 (2)
C13	0.7880 (2)	1.16903 (8)	0.72028 (11)	0.0186 (3)
H13A	0.7809	1.2230	0.7291	0.022*
C14	0.7570 (2)	1.13863 (8)	0.62170 (11)	0.0189 (3)
H14A	0.7279	1.1721	0.5631	0.023*
C15	0.9043 (2)	1.10800 (9)	0.99250 (11)	0.0196 (3)
H15A	1.0348	1.0825	1.0066	0.024*
H15B	0.8012	1.0678	0.9820	0.024*
C16	0.9131 (2)	1.15890 (9)	1.08336 (11)	0.0207 (3)
H16A	0.9521	1.1283	1.1479	0.031*
H16B	0.7815	1.1818	1.0702	0.031*
H16C	1.0116	1.1998	1.0912	0.031*
O1W	0.36756 (19)	0.59100 (6)	0.24443 (9)	0.0301 (3)
H3	0.4370	0.6177	0.2921	0.045*
H4	0.2664	0.6197	0.2059	0.045*
O2W	0.0731 (2)	0.67607 (8)	0.10548 (11)	0.0471 (4)
H5	−0.0331	0.6558	0.0590	0.071*
H6	0.0705	0.7267	0.0963	0.071*

	U11	U22	U33	U12	U13	U23
O1	0.0255 (5)	0.0134 (5)	0.0125 (4)	−0.0004 (3)	0.0059 (4)	0.0019 (4)
O2	0.0281 (5)	0.0179 (5)	0.0100 (4)	0.0064 (4)	0.0062 (4)	−0.0004 (4)
O3	0.0277 (5)	0.0181 (5)	0.0126 (5)	0.0025 (4)	0.0059 (4)	−0.0014 (4)
N1	0.0212 (5)	0.0134 (5)	0.0086 (5)	0.0002 (4)	0.0047 (4)	0.0005 (4)
N2	0.0184 (5)	0.0170 (5)	0.0097 (5)	−0.0007 (4)	0.0044 (4)	−0.0015 (4)
C1	0.0142 (5)	0.0133 (6)	0.0111 (5)	0.0001 (4)	0.0041 (4)	−0.0003 (4)
C2	0.0220 (6)	0.0125 (6)	0.0129 (6)	0.0000 (4)	0.0067 (5)	0.0008 (5)
C3	0.0223 (6)	0.0132 (6)	0.0132 (6)	0.0008 (4)	0.0063 (5)	−0.0010 (5)
C4	0.0159 (5)	0.0165 (6)	0.0103 (6)	0.0025 (4)	0.0037 (4)	0.0000 (4)
C5	0.0227 (6)	0.0142 (6)	0.0123 (6)	0.0039 (4)	0.0067 (5)	0.0025 (5)
C6	0.0211 (5)	0.0129 (6)	0.0134 (6)	0.0024 (4)	0.0070 (5)	0.0012 (5)
C7	0.0137 (5)	0.0139 (6)	0.0105 (5)	−0.0006 (4)	0.0042 (4)	0.0000 (4)
C8	0.0203 (5)	0.0161 (6)	0.0125 (6)	−0.0015 (4)	0.0061 (5)	−0.0004 (5)
C9	0.0173 (5)	0.0176 (6)	0.0117 (6)	−0.0005 (4)	0.0052 (4)	−0.0018 (5)
C10	0.0275 (6)	0.0163 (6)	0.0162 (7)	0.0028 (5)	0.0078 (5)	0.0004 (5)
C11	0.0274 (6)	0.0175 (6)	0.0140 (6)	0.0030 (5)	0.0055 (5)	0.0020 (5)
C12	0.0166 (5)	0.0184 (6)	0.0139 (6)	−0.0005 (4)	0.0043 (5)	−0.0032 (5)
C13	0.0246 (6)	0.0145 (6)	0.0168 (7)	0.0002 (5)	0.0075 (5)	−0.0005 (5)
C14	0.0247 (6)	0.0154 (6)	0.0169 (6)	−0.0012 (5)	0.0080 (5)	−0.0005 (5)
C15	0.0236 (6)	0.0212 (7)	0.0144 (6)	0.0014 (5)	0.0073 (5)	0.0014 (5)
C16	0.0235 (6)	0.0247 (7)	0.0137 (6)	−0.0009 (5)	0.0066 (5)	−0.0027 (5)
O1W	0.0463 (7)	0.0148 (5)	0.0187 (6)	0.0027 (5)	−0.0014 (5)	−0.0031 (4)
O2W	0.0469 (8)	0.0341 (8)	0.0342 (8)	0.0181 (6)	−0.0176 (6)	−0.0151 (6)

O1—C7	1.2445 (16)	C8—H8A	0.9500
O2—C4	1.3651 (16)	C9—C10	1.3957 (19)
O2—H1	0.8415	C9—C14	1.402 (2)
O3—C12	1.3738 (16)	C10—C11	1.388 (2)
O3—C15	1.4368 (17)	C10—H10A	0.9500
N1—C7	1.3428 (17)	C11—C12	1.397 (2)
N1—N2	1.3828 (15)	C11—H11A	0.9500
N1—H2	0.8479	C12—C13	1.387 (2)
N2—C8	1.2841 (18)	C13—C14	1.385 (2)
C1—C6	1.3977 (18)	C13—H13A	0.9500
C1—C2	1.3994 (18)	C14—H14A	0.9500
C1—C7	1.4894 (18)	C15—C16	1.504 (2)
C2—C3	1.3872 (19)	C15—H15A	0.9900
C2—H2A	0.9500	C15—H15B	0.9900
C3—C4	1.3906 (19)	C16—H16A	0.9800
C3—H3A	0.9500	C16—H16B	0.9800
C4—C5	1.3920 (19)	C16—H16C	0.9800
C5—C6	1.3890 (19)	O1W—H3	0.8092
C5—H5A	0.9500	O1W—H4	0.8829
C6—H6A	0.9500	O2W—H5	0.8715
C8—C9	1.4575 (18)	O2W—H6	0.8889
C4—O2—H1	109.6	C10—C9—C8	123.66 (13)
C12—O3—C15	118.06 (11)	C14—C9—C8	117.71 (12)
C7—N1—N2	118.98 (11)	C11—C10—C9	120.55 (13)
C7—N1—H2	123.0	C11—C10—H10A	119.7
N2—N1—H2	117.9	C9—C10—H10A	119.7
C8—N2—N1	114.02 (12)	C10—C11—C12	120.03 (13)
C6—C1—C2	118.69 (12)	C10—C11—H11A	120.0
C6—C1—C7	123.50 (12)	C12—C11—H11A	120.0
C2—C1—C7	117.77 (11)	O3—C12—C13	115.67 (12)
C3—C2—C1	121.23 (12)	O3—C12—C11	124.31 (13)
C3—C2—H2A	119.4	C13—C12—C11	120.02 (13)
C1—C2—H2A	119.4	C14—C13—C12	119.73 (13)
C2—C3—C4	119.37 (12)	C14—C13—H13A	120.1
C2—C3—H3A	120.3	C12—C13—H13A	120.1
C4—C3—H3A	120.3	C13—C14—C9	121.04 (13)
O2—C4—C3	122.42 (12)	C13—C14—H14A	119.5
O2—C4—C5	117.41 (12)	C9—C14—H14A	119.5
C3—C4—C5	120.16 (12)	O3—C15—C16	107.82 (12)
C6—C5—C4	120.21 (12)	O3—C15—H15A	110.1
C6—C5—H5A	119.9	C16—C15—H15A	110.1
C4—C5—H5A	119.9	O3—C15—H15B	110.1
C5—C6—C1	120.31 (12)	C16—C15—H15B	110.1
C5—C6—H6A	119.8	H15A—C15—H15B	108.5
C1—C6—H6A	119.8	C15—C16—H16A	109.5
O1—C7—N1	120.81 (12)	C15—C16—H16B	109.5
O1—C7—C1	121.40 (12)	H16A—C16—H16B	109.5
N1—C7—C1	117.78 (11)	C15—C16—H16C	109.5
N2—C8—C9	122.96 (13)	H16A—C16—H16C	109.5
N2—C8—H8A	118.5	H16B—C16—H16C	109.5
C9—C8—H8A	118.5	H3—O1W—H4	106.9
C10—C9—C14	118.62 (12)	H5—O2W—H6	109.2
C7—N1—N2—C8	−176.66 (11)	N1—N2—C8—C9	−179.90 (11)
C6—C1—C2—C3	0.32 (18)	N2—C8—C9—C10	−6.5 (2)
C7—C1—C2—C3	−177.23 (11)	N2—C8—C9—C14	174.70 (12)
C1—C2—C3—C4	0.81 (19)	C14—C9—C10—C11	0.4 (2)
C2—C3—C4—O2	178.72 (11)	C8—C9—C10—C11	−178.38 (12)
C2—C3—C4—C5	−1.92 (19)	C9—C10—C11—C12	−0.6 (2)
O2—C4—C5—C6	−178.70 (11)	C15—O3—C12—C13	−178.41 (11)
C3—C4—C5—C6	1.91 (19)	C15—O3—C12—C11	1.97 (18)
C4—C5—C6—C1	−0.77 (19)	C10—C11—C12—O3	179.87 (12)
C2—C1—C6—C5	−0.34 (18)	C10—C11—C12—C13	0.3 (2)
C7—C1—C6—C5	177.06 (11)	O3—C12—C13—C14	−179.40 (12)
N2—N1—C7—O1	1.17 (17)	C11—C12—C13—C14	0.2 (2)
N2—N1—C7—C1	−177.57 (10)	C12—C13—C14—C9	−0.4 (2)
C6—C1—C7—O1	−173.58 (12)	C10—C9—C14—C13	0.1 (2)
C2—C1—C7—O1	3.85 (17)	C8—C9—C14—C13	178.96 (12)
C6—C1—C7—N1	5.15 (17)	C12—O3—C15—C16	−176.58 (11)
C2—C1—C7—N1	−177.43 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1i	0.84	1.77	2.6106 (15)	174
N1—H2···O1Wii	0.85	2.10	2.9278 (16)	167
O1W—H3···O2iii	0.81	2.06	2.8683 (15)	177
O1W—H4···O2W	0.88	1.84	2.7159 (19)	169
O2W—H5···O1iv	0.87	2.14	2.8558 (18)	139
O2W—H5···N2iv	0.87	2.55	3.3363 (19)	151
O2W—H6···O3v	0.89	2.11	2.9791 (17)	165
C6—H6A···O1Wii	0.95	2.36	3.2942 (18)	169
C8—H8A···O1Wii	0.95	2.49	3.3222 (18)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O1i	0.84	1.77	2.6106 (15)	174
N1—H2⋯O1Wii	0.85	2.10	2.9278 (16)	167
O1W—H3⋯O2iii	0.81	2.06	2.8683 (15)	177
O1W—H4⋯O2W	0.88	1.84	2.7159 (19)	169
O2W—H5⋯O1iv	0.87	2.14	2.8558 (18)	139
O2W—H5⋯N2iv	0.87	2.55	3.3363 (19)	151
O2W—H6⋯O3v	0.89	2.11	2.9791 (17)	165
C6—H6A⋯O1Wii	0.95	2.36	3.2942 (18)	169
C8—H8A⋯O1Wii	0.95	2.49	3.3222 (18)	146

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