N'-(4-Hydr-oxy-3-methoxy-benzyl-idene)-4-methoxy-benzohydrazide monohydrate.

In the title compound, C(16)H(16)N(2)O(4)·H(2)O, the dihedral angle between the two aromatic rings is 19.6 (2)°. In the crystal structure, mol-ecules are linked into a three-dimensional network by inter-molecular N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds.

Related literature

For our previous work in this area, see: Lu et al. (2008a ▶,b ▶,c ▶). For related structures, see: Abdul Alhadi et al. (2009 ▶); Mohd Lair et al. (2009 ▶); Narayana et al. (2007 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H16N2O4·H2O

M = 318.32

Monoclinic,

a = 7.942 (1) Å

b = 21.273 (2) Å

c = 10.246 (1) Å

β = 106.596 (2)°

V = 1659.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.32 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.970, T max = 0.972

9533 measured reflections

3338 independent reflections

2291 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.04

3338 reflections

220 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034242/hb5071sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034242/hb5071Isup2.hkl

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

C16H16N2O4·H2O	F(000) = 672
Mr = 318.32	Dx = 1.274 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2203 reflections
a = 7.942 (1) Å	θ = 2.3–24.6°
b = 21.273 (2) Å	µ = 0.10 mm−1
c = 10.246 (1) Å	T = 298 K
β = 106.596 (2)°	Block, colourless
V = 1659.0 (3) Å3	0.32 × 0.30 × 0.30 mm
Z = 4

Bruker APEXII CCD diffractometer	3338 independent reflections
Radiation source: fine-focus sealed tube	2291 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 26.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.970, Tmax = 0.972	k = −26→25
9533 measured reflections	l = −12→11

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.2417P] where P = (Fo2 + 2Fc2)/3
3338 reflections	(Δ/σ)max = 0.001
220 parameters	Δρmax = 0.20 e Å−3
4 restraints	Δρmin = −0.18 e Å−3

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	0.45414 (18)	0.25435 (6)	−0.34503 (15)	0.0726 (4)
O2	0.25510 (15)	0.15740 (6)	−0.42933 (13)	0.0570 (3)
H2	0.1742	0.1332	−0.4638	0.085*
O3	0.32814 (18)	0.47213 (6)	0.11553 (15)	0.0682 (4)
O4	−0.1311 (2)	0.60007 (7)	0.46039 (15)	0.0791 (4)
O5	0.01680 (17)	0.08043 (6)	0.43784 (15)	0.0612 (4)
N1	0.16872 (18)	0.37019 (6)	−0.01397 (14)	0.0489 (4)
N2	0.10078 (19)	0.40488 (7)	0.07401 (15)	0.0508 (4)
C1	0.1256 (2)	0.28010 (8)	−0.15935 (17)	0.0477 (4)
C2	0.2726 (2)	0.29018 (8)	−0.20479 (17)	0.0487 (4)
H2A	0.3435	0.3251	−0.1744	0.058*
C3	0.3135 (2)	0.24897 (8)	−0.29416 (17)	0.0475 (4)
C4	0.2067 (2)	0.19639 (8)	−0.34092 (17)	0.0456 (4)
C5	0.0626 (2)	0.18616 (9)	−0.29573 (19)	0.0562 (5)
H5	−0.0079	0.1511	−0.3256	0.067*
C6	0.0218 (2)	0.22785 (9)	−0.2059 (2)	0.0600 (5)
H6	−0.0768	0.2207	−0.1762	0.072*
C7	0.5593 (3)	0.30919 (11)	−0.3109 (3)	0.0894 (8)
H7A	0.4872	0.3458	−0.3389	0.134*
H7B	0.6494	0.3084	−0.3565	0.134*
H7C	0.6125	0.3105	−0.2142	0.134*
C8	0.0764 (2)	0.32266 (8)	−0.06566 (18)	0.0512 (4)
H8	−0.0267	0.3149	−0.0425	0.061*
C9	0.1854 (2)	0.45679 (8)	0.13293 (18)	0.0507 (4)
C10	0.1005 (2)	0.49380 (8)	0.21918 (18)	0.0510 (4)
C11	0.1991 (3)	0.53788 (10)	0.3066 (2)	0.0729 (6)
H11	0.3163	0.5435	0.3099	0.087*
C12	0.1273 (3)	0.57418 (10)	0.3899 (2)	0.0757 (6)
H12	0.1966	0.6033	0.4491	0.091*
C13	−0.0457 (3)	0.56687 (9)	0.38450 (19)	0.0602 (5)
C14	−0.1466 (3)	0.52298 (9)	0.2976 (2)	0.0623 (5)
H14	−0.2638	0.5174	0.2945	0.075*
C15	−0.0741 (3)	0.48746 (8)	0.21579 (19)	0.0568 (5)
H15	−0.1440	0.4584	0.1566	0.068*
C16	−0.0366 (4)	0.64796 (11)	0.5474 (2)	0.0959 (8)
H16A	0.0642	0.6299	0.6119	0.144*
H16B	−0.1111	0.6672	0.5951	0.144*
H16C	0.0012	0.6791	0.4941	0.144*
H2B	0.0004 (18)	0.3933 (10)	0.090 (2)	0.080*
H5B	0.064 (2)	0.0464 (7)	0.421 (2)	0.080*
H5A	−0.064 (2)	0.0719 (9)	0.473 (2)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0662 (8)	0.0727 (9)	0.0998 (10)	−0.0254 (7)	0.0572 (8)	−0.0298 (8)
O2	0.0520 (7)	0.0565 (7)	0.0720 (8)	−0.0056 (6)	0.0329 (7)	−0.0161 (6)
O3	0.0697 (9)	0.0606 (8)	0.0880 (10)	−0.0194 (7)	0.0443 (8)	−0.0096 (7)
O4	0.1010 (11)	0.0712 (9)	0.0694 (9)	0.0105 (8)	0.0311 (8)	−0.0178 (8)
O5	0.0558 (8)	0.0502 (7)	0.0862 (10)	−0.0013 (6)	0.0342 (7)	−0.0118 (7)
N1	0.0522 (8)	0.0479 (8)	0.0549 (8)	−0.0001 (7)	0.0285 (7)	−0.0016 (7)
N2	0.0560 (9)	0.0487 (8)	0.0582 (9)	−0.0065 (7)	0.0329 (7)	−0.0072 (7)
C1	0.0480 (9)	0.0491 (9)	0.0524 (10)	−0.0014 (7)	0.0249 (8)	−0.0019 (8)
C2	0.0498 (10)	0.0460 (9)	0.0557 (10)	−0.0071 (8)	0.0241 (8)	−0.0036 (8)
C3	0.0423 (9)	0.0515 (9)	0.0561 (10)	−0.0040 (7)	0.0259 (8)	−0.0023 (8)
C4	0.0455 (9)	0.0455 (9)	0.0509 (10)	0.0010 (7)	0.0219 (8)	−0.0026 (7)
C5	0.0515 (10)	0.0550 (10)	0.0704 (12)	−0.0125 (8)	0.0307 (9)	−0.0129 (9)
C6	0.0529 (11)	0.0630 (11)	0.0772 (13)	−0.0131 (9)	0.0397 (10)	−0.0128 (10)
C7	0.0736 (14)	0.0922 (16)	0.125 (2)	−0.0380 (13)	0.0656 (15)	−0.0365 (15)
C8	0.0509 (10)	0.0531 (10)	0.0587 (11)	−0.0051 (8)	0.0304 (8)	−0.0027 (8)
C9	0.0588 (11)	0.0451 (9)	0.0536 (10)	−0.0068 (8)	0.0247 (8)	0.0040 (8)
C10	0.0649 (11)	0.0415 (9)	0.0511 (10)	−0.0042 (8)	0.0238 (9)	0.0016 (8)
C11	0.0790 (14)	0.0676 (13)	0.0817 (14)	−0.0244 (11)	0.0383 (12)	−0.0179 (11)
C12	0.0937 (17)	0.0644 (13)	0.0748 (14)	−0.0245 (12)	0.0335 (12)	−0.0234 (11)
C13	0.0831 (14)	0.0490 (10)	0.0522 (11)	0.0069 (10)	0.0252 (10)	−0.0008 (8)
C14	0.0600 (12)	0.0637 (12)	0.0634 (12)	0.0082 (9)	0.0179 (10)	−0.0075 (10)
C15	0.0593 (11)	0.0528 (10)	0.0574 (11)	0.0019 (8)	0.0151 (9)	−0.0089 (9)
C16	0.136 (2)	0.0756 (14)	0.0731 (15)	0.0114 (15)	0.0258 (15)	−0.0260 (13)

O1—C3	1.3654 (19)	C5—H5	0.9300
O1—C7	1.419 (2)	C6—H6	0.9300
O2—C4	1.3622 (19)	C7—H7A	0.9600
O2—H2	0.8200	C7—H7B	0.9600
O3—C9	1.241 (2)	C7—H7C	0.9600
O4—C13	1.365 (2)	C8—H8	0.9300
O4—C16	1.419 (3)	C9—C10	1.482 (2)
O5—H5B	0.856 (9)	C10—C11	1.376 (3)
O5—H5A	0.846 (9)	C10—C15	1.384 (3)
N1—C8	1.272 (2)	C11—C12	1.388 (3)
N1—N2	1.3878 (18)	C11—H11	0.9300
N2—C9	1.343 (2)	C12—C13	1.369 (3)
N2—H2B	0.895 (9)	C12—H12	0.9300
C1—C6	1.385 (2)	C13—C14	1.378 (3)
C1—C2	1.391 (2)	C14—C15	1.372 (2)
C1—C8	1.452 (2)	C14—H14	0.9300
C2—C3	1.372 (2)	C15—H15	0.9300
C2—H2A	0.9300	C16—H16A	0.9600
C3—C4	1.403 (2)	C16—H16B	0.9600
C4—C5	1.369 (2)	C16—H16C	0.9600
C5—C6	1.382 (2)
C3—O1—C7	117.57 (14)	H7B—C7—H7C	109.5
C4—O2—H2	109.5	N1—C8—C1	122.59 (15)
C13—O4—C16	117.99 (19)	N1—C8—H8	118.7
H5B—O5—H5A	109.9 (17)	C1—C8—H8	118.7
C8—N1—N2	114.08 (13)	O3—C9—N2	120.79 (16)
C9—N2—N1	119.46 (14)	O3—C9—C10	122.43 (15)
C9—N2—H2B	120.1 (14)	N2—C9—C10	116.78 (15)
N1—N2—H2B	120.5 (14)	C11—C10—C15	117.57 (17)
C6—C1—C2	118.84 (15)	C11—C10—C9	118.60 (17)
C6—C1—C8	118.80 (15)	C15—C10—C9	123.83 (16)
C2—C1—C8	122.36 (15)	C10—C11—C12	121.5 (2)
C3—C2—C1	120.41 (15)	C10—C11—H11	119.3
C3—C2—H2A	119.8	C12—C11—H11	119.3
C1—C2—H2A	119.8	C13—C12—C11	119.72 (19)
O1—C3—C2	125.22 (15)	C13—C12—H12	120.1
O1—C3—C4	114.67 (14)	C11—C12—H12	120.1
C2—C3—C4	120.11 (14)	O4—C13—C12	125.08 (18)
O2—C4—C5	123.37 (15)	O4—C13—C14	115.25 (19)
O2—C4—C3	117.03 (14)	C12—C13—C14	119.67 (18)
C5—C4—C3	119.59 (15)	C15—C14—C13	120.01 (19)
C4—C5—C6	120.06 (16)	C15—C14—H14	120.0
C4—C5—H5	120.0	C13—C14—H14	120.0
C6—C5—H5	120.0	C14—C15—C10	121.56 (17)
C5—C6—C1	120.98 (16)	C14—C15—H15	119.2
C5—C6—H6	119.5	C10—C15—H15	119.2
C1—C6—H6	119.5	O4—C16—H16A	109.5
O1—C7—H7A	109.5	O4—C16—H16B	109.5
O1—C7—H7B	109.5	H16A—C16—H16B	109.5
H7A—C7—H7B	109.5	O4—C16—H16C	109.5
O1—C7—H7C	109.5	H16A—C16—H16C	109.5
H7A—C7—H7C	109.5	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···N1i	0.85 (1)	2.49 (2)	3.1257 (18)	133 (2)
O5—H5A···O3i	0.85 (1)	2.11 (1)	2.8927 (18)	154 (2)
O5—H5B···O3ii	0.86 (1)	1.88 (1)	2.7401 (17)	179 (2)
N2—H2B···O2i	0.90 (1)	2.19 (1)	3.0398 (18)	160 (2)
O2—H2···O5iii	0.82	1.77	2.5775 (17)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯N1i	0.846 (9)	2.487 (15)	3.1257 (18)	133.0 (17)
O5—H5A⋯O3i	0.846 (9)	2.107 (13)	2.8927 (18)	154 (2)
O5—H5B⋯O3ii	0.856 (9)	1.884 (10)	2.7401 (17)	179 (2)
N2—H2B⋯O2i	0.895 (9)	2.185 (12)	3.0398 (18)	159.6 (19)
O2—H2⋯O5iii	0.82	1.77	2.5775 (17)	170

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