(E)-N'-(3,4-Dihy-droxy-benzyl-idene)-2,4-dimethyl-benzohydrazide monohydrate.

In the title compound, C16H16N2O3·H2O, the dihedral angle between the benzene rings is 30.27 (7)°. In the crystal, the components are linked by N-H⋯O, O-H⋯O and C-H⋯O inter-actions into a three-dimensional network.

Related literature

For the applications and biological activity of Schiff bases, see: Musharraf et al. (2012 ▶); Khan et al. (2012 ▶). For the crystal structures of related compounds, see: Taha et al. (2012 ▶); Baharudin et al. (2012 ▶).

Experimental

Crystal data

C16H16N2O3·H2O

M = 302.32

Monoclinic,

a = 8.1373 (3) Å

b = 13.9025 (5) Å

c = 13.7886 (5) Å

β = 92.913 (1)°

V = 1557.87 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.973, T max = 0.991

9012 measured reflections

2897 independent reflections

2535 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.05

2897 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005692/pv2622sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005692/pv2622Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005692/pv2622Isup3.cml

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

C16H16N2O3·H2O	F(000) = 640
Mr = 302.32	Dx = 1.289 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4856 reflections
a = 8.1373 (3) Å	θ = 2.8–28.2°
b = 13.9025 (5) Å	µ = 0.09 mm−1
c = 13.7886 (5) Å	T = 298 K
β = 92.913 (1)°	Block, brown
V = 1557.87 (10) Å3	0.30 × 0.10 × 0.10 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2897 independent reflections
Radiation source: fine-focus sealed tube	2535 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scan	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.973, Tmax = 0.991	k = −16→16
9012 measured reflections	l = −16→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.3352P] where P = (Fo2 + 2Fc2)/3
2897 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.28 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
O1	0.15363 (13)	0.55077 (8)	−0.16328 (8)	0.0569 (3)
O1W	−0.12355 (15)	0.45259 (10)	−0.07769 (9)	0.0612 (3)
O2	−0.04800 (12)	0.26761 (9)	0.22605 (8)	0.0505 (3)
O3	0.16469 (13)	0.15980 (8)	0.32684 (7)	0.0460 (3)
N1	0.34634 (15)	0.43523 (9)	−0.14057 (9)	0.0454 (3)
N2	0.28104 (14)	0.40196 (9)	−0.05580 (8)	0.0435 (3)
C1	0.30375 (16)	0.56844 (10)	−0.36100 (10)	0.0395 (3)
C2	0.40413 (18)	0.60048 (11)	−0.43273 (10)	0.0446 (3)
H2C	0.3561	0.6153	−0.4935	0.054*
C3	0.57324 (17)	0.61142 (11)	−0.41767 (10)	0.0435 (3)
C4	0.64410 (17)	0.58608 (11)	−0.32796 (11)	0.0455 (4)
H4A	0.7574	0.5911	−0.3166	0.055*
C5	0.54846 (16)	0.55358 (10)	−0.25556 (10)	0.0423 (3)
H5A	0.5981	0.5371	−0.1956	0.051*
C6	0.37828 (16)	0.54484 (9)	−0.27016 (10)	0.0366 (3)
C7	0.28131 (16)	0.51150 (10)	−0.18789 (10)	0.0397 (3)
C8	0.35766 (18)	0.33077 (11)	−0.01702 (11)	0.0464 (4)
H8A	0.4495	0.3069	−0.0465	0.056*
C9	0.30656 (17)	0.28538 (10)	0.07190 (10)	0.0421 (3)
C10	0.41516 (19)	0.22570 (11)	0.12370 (12)	0.0514 (4)
H10A	0.5192	0.2145	0.1011	0.062*
C11	0.37047 (19)	0.18256 (11)	0.20869 (12)	0.0499 (4)
H11A	0.4448	0.1431	0.2432	0.060*
C12	0.21552 (16)	0.19792 (9)	0.24262 (10)	0.0390 (3)
C13	0.10379 (16)	0.25680 (10)	0.18973 (10)	0.0376 (3)
C14	0.14912 (16)	0.29972 (10)	0.10553 (10)	0.0392 (3)
H14A	0.0745	0.3387	0.0705	0.047*
C15	0.12199 (18)	0.55713 (14)	−0.38483 (12)	0.0571 (4)
H15A	0.1029	0.5506	−0.4538	0.086*
H15B	0.0648	0.6128	−0.3628	0.086*
H15C	0.0825	0.5008	−0.3531	0.086*
C16	0.6765 (2)	0.65068 (14)	−0.49624 (13)	0.0615 (5)
H16A	0.6324	0.6293	−0.5584	0.092*
H16B	0.7875	0.6280	−0.4863	0.092*
H16C	0.6755	0.7197	−0.4941	0.092*
H2A	−0.099 (3)	0.3180 (16)	0.1996 (15)	0.077 (6)*
H1A	0.436 (2)	0.4053 (13)	−0.1634 (13)	0.061 (5)*
H1W1	−0.165 (3)	0.4883 (17)	−0.0335 (16)	0.080 (7)*
H3A	0.239 (2)	0.1248 (15)	0.3533 (15)	0.071 (6)*
H2W1	−0.029 (3)	0.4798 (17)	−0.1022 (16)	0.091 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0495 (6)	0.0633 (7)	0.0601 (7)	0.0209 (5)	0.0261 (5)	0.0182 (5)
O1W	0.0486 (6)	0.0766 (9)	0.0595 (7)	−0.0124 (6)	0.0122 (5)	−0.0274 (6)
O2	0.0399 (5)	0.0578 (7)	0.0557 (7)	0.0085 (5)	0.0200 (5)	0.0140 (5)
O3	0.0453 (6)	0.0499 (6)	0.0442 (6)	0.0056 (5)	0.0153 (5)	0.0141 (5)
N1	0.0462 (6)	0.0506 (7)	0.0414 (7)	0.0134 (6)	0.0227 (5)	0.0112 (5)
N2	0.0453 (6)	0.0477 (7)	0.0393 (6)	0.0066 (5)	0.0194 (5)	0.0077 (5)
C1	0.0360 (7)	0.0429 (7)	0.0400 (7)	0.0004 (5)	0.0051 (6)	0.0011 (6)
C2	0.0478 (8)	0.0505 (8)	0.0358 (7)	0.0008 (6)	0.0041 (6)	0.0062 (6)
C3	0.0437 (7)	0.0430 (8)	0.0448 (8)	−0.0010 (6)	0.0136 (6)	0.0037 (6)
C4	0.0335 (7)	0.0506 (8)	0.0530 (9)	−0.0033 (6)	0.0068 (6)	0.0038 (7)
C5	0.0383 (7)	0.0488 (8)	0.0396 (7)	0.0023 (6)	0.0014 (6)	0.0048 (6)
C6	0.0360 (7)	0.0379 (7)	0.0367 (7)	0.0023 (5)	0.0085 (5)	0.0023 (5)
C7	0.0378 (7)	0.0434 (7)	0.0387 (7)	0.0050 (6)	0.0105 (6)	0.0030 (6)
C8	0.0484 (8)	0.0466 (8)	0.0463 (8)	0.0108 (7)	0.0218 (6)	0.0064 (7)
C9	0.0468 (8)	0.0393 (7)	0.0418 (7)	0.0055 (6)	0.0176 (6)	0.0046 (6)
C10	0.0468 (8)	0.0526 (9)	0.0572 (9)	0.0149 (7)	0.0263 (7)	0.0122 (7)
C11	0.0469 (8)	0.0496 (9)	0.0547 (9)	0.0156 (7)	0.0171 (7)	0.0154 (7)
C12	0.0441 (7)	0.0352 (7)	0.0388 (7)	0.0008 (6)	0.0145 (6)	0.0039 (5)
C13	0.0370 (7)	0.0365 (7)	0.0405 (7)	0.0007 (5)	0.0128 (5)	−0.0002 (5)
C14	0.0420 (7)	0.0361 (7)	0.0401 (7)	0.0036 (6)	0.0082 (6)	0.0034 (6)
C15	0.0401 (8)	0.0788 (12)	0.0521 (9)	−0.0036 (7)	−0.0010 (7)	0.0037 (8)
C16	0.0567 (9)	0.0699 (11)	0.0598 (10)	−0.0030 (8)	0.0225 (8)	0.0146 (9)

O1—C7	1.2364 (16)	C5—C6	1.3945 (19)
O1W—H1W1	0.87 (2)	C5—H5A	0.9300
O1W—H2W1	0.94 (2)	C6—C7	1.4884 (18)
O2—C13	1.3645 (15)	C8—C9	1.4581 (19)
O2—H2A	0.88 (2)	C8—H8A	0.9300
O3—C12	1.3599 (16)	C9—C10	1.384 (2)
O3—H3A	0.85 (2)	C9—C14	1.3988 (19)
N1—C7	1.3398 (18)	C10—C11	1.382 (2)
N1—N2	1.3877 (15)	C10—H10A	0.9300
N1—H1A	0.913 (19)	C11—C12	1.3835 (19)
N2—C8	1.2729 (19)	C11—H11A	0.9300
C1—C2	1.3878 (19)	C12—C13	1.4004 (19)
C1—C6	1.4026 (19)	C13—C14	1.3725 (19)
C1—C15	1.5069 (19)	C14—H14A	0.9300
C2—C3	1.390 (2)	C15—H15A	0.9600
C2—H2C	0.9300	C15—H15B	0.9600
C3—C4	1.384 (2)	C15—H15C	0.9600
C3—C16	1.507 (2)	C16—H16A	0.9600
C4—C5	1.373 (2)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
H1W1—O1W—H2W1	112 (2)	C10—C9—C14	119.07 (13)
C13—O2—H2A	110.5 (13)	C10—C9—C8	119.44 (12)
C12—O3—H3A	110.4 (13)	C14—C9—C8	121.48 (13)
C7—N1—N2	121.02 (11)	C11—C10—C9	120.62 (13)
C7—N1—H1A	119.8 (11)	C11—C10—H10A	119.7
N2—N1—H1A	119.2 (11)	C9—C10—H10A	119.7
C8—N2—N1	114.37 (11)	C10—C11—C12	120.24 (14)
C2—C1—C6	117.91 (12)	C10—C11—H11A	119.9
C2—C1—C15	119.00 (13)	C12—C11—H11A	119.9
C6—C1—C15	123.05 (12)	O3—C12—C11	123.41 (13)
C1—C2—C3	122.88 (13)	O3—C12—C13	117.06 (11)
C1—C2—H2C	118.6	C11—C12—C13	119.52 (12)
C3—C2—H2C	118.6	O2—C13—C14	123.35 (12)
C4—C3—C2	118.05 (13)	O2—C13—C12	116.69 (12)
C4—C3—C16	120.85 (13)	C14—C13—C12	119.96 (12)
C2—C3—C16	121.10 (13)	C13—C14—C9	120.57 (13)
C5—C4—C3	120.53 (13)	C13—C14—H14A	119.7
C5—C4—H4A	119.7	C9—C14—H14A	119.7
C3—C4—H4A	119.7	C1—C15—H15A	109.5
C4—C5—C6	121.27 (13)	C1—C15—H15B	109.5
C4—C5—H5A	119.4	H15A—C15—H15B	109.5
C6—C5—H5A	119.4	C1—C15—H15C	109.5
C5—C6—C1	119.32 (12)	H15A—C15—H15C	109.5
C5—C6—C7	118.57 (12)	H15B—C15—H15C	109.5
C1—C6—C7	122.11 (12)	C3—C16—H16A	109.5
O1—C7—N1	122.17 (12)	C3—C16—H16B	109.5
O1—C7—C6	123.86 (12)	H16A—C16—H16B	109.5
N1—C7—C6	113.96 (11)	C3—C16—H16C	109.5
N2—C8—C9	122.36 (12)	H16A—C16—H16C	109.5
N2—C8—H8A	118.8	H16B—C16—H16C	109.5
C9—C8—H8A	118.8
C7—N1—N2—C8	−178.10 (14)	C5—C6—C7—N1	−45.73 (18)
C6—C1—C2—C3	−1.1 (2)	C1—C6—C7—N1	134.90 (14)
C15—C1—C2—C3	−178.87 (15)	N1—N2—C8—C9	−179.45 (13)
C1—C2—C3—C4	2.2 (2)	N2—C8—C9—C10	−163.72 (16)
C1—C2—C3—C16	−177.21 (15)	N2—C8—C9—C14	17.1 (2)
C2—C3—C4—C5	−1.7 (2)	C14—C9—C10—C11	−1.5 (2)
C16—C3—C4—C5	177.66 (15)	C8—C9—C10—C11	179.34 (15)
C3—C4—C5—C6	0.2 (2)	C9—C10—C11—C12	0.6 (3)
C4—C5—C6—C1	0.9 (2)	C10—C11—C12—O3	−178.29 (14)
C4—C5—C6—C7	−178.49 (13)	C10—C11—C12—C13	0.6 (2)
C2—C1—C6—C5	−0.5 (2)	O3—C12—C13—O2	−2.27 (19)
C15—C1—C6—C5	177.23 (14)	C11—C12—C13—O2	178.79 (14)
C2—C1—C6—C7	178.88 (13)	O3—C12—C13—C14	178.14 (12)
C15—C1—C6—C7	−3.4 (2)	C11—C12—C13—C14	−0.8 (2)
N2—N1—C7—O1	−5.9 (2)	O2—C13—C14—C9	−179.69 (13)
N2—N1—C7—C6	172.84 (12)	C12—C13—C14—C9	−0.1 (2)
C5—C6—C7—O1	133.03 (16)	C10—C9—C14—C13	1.3 (2)
C1—C6—C7—O1	−46.3 (2)	C8—C9—C14—C13	−179.59 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N2i	0.87 (2)	2.20 (2)	3.059 (2)	169 (2)
N1—H1A···O3ii	0.91 (2)	2.08 (2)	2.962 (2)	163 (2)
O1W—H2W1···O1	0.94 (2)	2.01 (2)	2.935 (2)	173 (2)
O2—H2A···O1i	0.88 (2)	1.94 (2)	2.791 (2)	162 (2)
O3—H3A···O1Wiii	0.85 (2)	1.79 (2)	2.629 (2)	172 (2)
C8—H8A···O3ii	0.93	2.58	3.382 (2)	145
C15—H15B···O2i	0.96	2.52	3.351 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯N2i	0.87 (2)	2.20 (2)	3.059 (2)	169 (2)
O1W—H2W1⋯O1	0.94 (2)	2.01 (2)	2.935 (2)	173 (2)
N1—H1A⋯O3ii	0.91 (2)	2.08 (2)	2.962 (2)	163 (2)
O2—H2A⋯O1i	0.88 (2)	1.94 (2)	2.791 (2)	162 (2)
O3—H3A⋯O1W iii	0.85 (2)	1.79 (2)	2.629 (2)	172 (2)
C8—H8A⋯O3ii	0.93	2.58	3.382 (2)	145
C15—H15B⋯O2i	0.96	2.52	3.351 (2)	144

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