2-(4-Chloro-phen-oxy)-N'-[2-(4-chloro-phen-oxy)acet-yl]acetohydrazide monohydrate.

In the title compound, C(16)H(14)Cl(2)N(2)O(4)·H(2)O, the hydrazine and water mol-ecules are both located on twofold axes. The C-N-N-C torsion angle is -72.66 (1)° and the dihedral angle between the two benzene rings is 67.33 (1)°. In the crystal, mol-ecules are linked into a layer structure by a combination of O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds. Adjacent layers are linked into a three-dimensional network by Cl⋯Cl inter-actions [3.400 (2) Å]. C-H⋯π inter-actions are also observed.

Related literature

For the synthesis and biological activity of title compound and its derivatives, see: Dovlatvan (1961 ▶). For the synthesis and biological activity of diacyl­hydrazine derivatives, see: Jia (2008 ▶); Zhang et al. (2005 ▶); Zhao et al. (2008 ▶). For a related structure, see: Jiang et al. (2009 ▶).

Experimental

Crystal data

C16H14Cl2N2O4·H2O

M = 387.21

Monoclinic,

a = 4.8462 (9) Å

b = 5.4411 (10) Å

c = 33.521 (6) Å

β = 90.840 (3)°

V = 883.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 292 K

0.10 × 0.04 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer

9670 measured reflections

2013 independent reflections

1380 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.169

S = 1.06

2013 reflections

121 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 I, global. DOI: 10.1107/S160053681004050X/vm2047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004050X/vm2047Isup2.hkl

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

C16H14Cl2N2O4·H2O	F(000) = 400
Mr = 387.21	Dx = 1.455 Mg m−3
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 2333 reflections
a = 4.8462 (9) Å	θ = 3.7–26.5°
b = 5.4411 (10) Å	µ = 0.40 mm−1
c = 33.521 (6) Å	T = 292 K
β = 90.840 (3)°	Block, colourless
V = 883.8 (3) Å3	0.10 × 0.04 × 0.02 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	1380 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
graphite	θmax = 27.5°, θmin = 1.2°
phi and ω scans	h = −6→6
9670 measured reflections	k = −6→6
2013 independent reflections	l = −43→43

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0947P)2] where P = (Fo2 + 2Fc2)/3
2013 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.34 e Å−3
2 restraints	Δρmin = −0.27 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
C1	0.3940 (6)	0.2592 (5)	0.43058 (8)	0.0523 (7)
C2	0.5608 (6)	0.4610 (6)	0.43082 (7)	0.0596 (8)
H2	0.5626	0.5664	0.4527	0.072*
C3	0.3829 (6)	0.1066 (5)	0.39794 (9)	0.0585 (7)
H3	0.2647	−0.0281	0.3977	0.070*
C4	0.7276 (5)	0.5091 (5)	0.39850 (7)	0.0504 (7)
H4	0.8425	0.6460	0.3987	0.060*
C5	0.5469 (5)	0.1529 (5)	0.36551 (8)	0.0499 (6)
H5	0.5394	0.0499	0.3434	0.060*
C6	0.7225 (5)	0.3534 (4)	0.36602 (6)	0.0389 (5)
C7	1.0585 (5)	0.5868 (4)	0.33195 (7)	0.0412 (6)
H7A	1.1768	0.5850	0.3556	0.049*
H7B	0.9502	0.7367	0.3324	0.049*
C8	1.2341 (5)	0.5841 (4)	0.29520 (6)	0.0391 (5)
Cl1	0.1904 (2)	0.1932 (2)	0.47157 (2)	0.0884 (4)
O1	0.8805 (3)	0.3820 (3)	0.33266 (4)	0.0459 (5)
O2	1.4157 (4)	0.7389 (3)	0.29242 (6)	0.0582 (5)
N1	1.1790 (4)	0.4132 (4)	0.26786 (5)	0.0394 (5)
O3	0.7500	0.0536 (4)	0.2500	0.0484 (6)
H1	1.042 (4)	0.316 (5)	0.2707 (9)	0.066 (9)*
H3A	0.636 (6)	−0.036 (6)	0.2602 (11)	0.099*

	U11	U22	U33	U12	U13	U23
C1	0.0490 (15)	0.0682 (17)	0.0399 (14)	−0.0006 (12)	0.0127 (11)	0.0082 (12)
C2	0.0648 (18)	0.080 (2)	0.0345 (13)	−0.0098 (15)	0.0128 (12)	−0.0117 (13)
C3	0.0557 (16)	0.0530 (16)	0.0673 (18)	−0.0132 (12)	0.0187 (13)	0.0008 (13)
C4	0.0531 (15)	0.0583 (16)	0.0400 (13)	−0.0155 (12)	0.0092 (11)	−0.0082 (11)
C5	0.0516 (15)	0.0500 (14)	0.0485 (15)	−0.0076 (12)	0.0129 (11)	−0.0088 (11)
C6	0.0358 (12)	0.0482 (13)	0.0330 (12)	0.0004 (10)	0.0064 (9)	−0.0009 (9)
C7	0.0433 (13)	0.0442 (13)	0.0363 (12)	−0.0054 (10)	0.0079 (10)	−0.0026 (10)
C8	0.0381 (12)	0.0435 (13)	0.0357 (12)	−0.0001 (10)	0.0051 (9)	0.0044 (10)
Cl1	0.0842 (6)	0.1257 (8)	0.0562 (5)	−0.0160 (5)	0.0333 (4)	0.0175 (4)
O1	0.0480 (10)	0.0540 (10)	0.0362 (9)	−0.0121 (8)	0.0154 (7)	−0.0079 (7)
O2	0.0606 (12)	0.0641 (12)	0.0504 (11)	−0.0269 (9)	0.0149 (9)	−0.0052 (8)
N1	0.0383 (11)	0.0435 (11)	0.0368 (10)	−0.0052 (9)	0.0135 (8)	−0.0018 (8)
O3	0.0477 (15)	0.0424 (14)	0.0558 (15)	0.000	0.0216 (11)	0.000

C1—C2	1.363 (4)	C6—O1	1.373 (2)
C1—C3	1.374 (4)	C7—O1	1.410 (3)
C1—Cl1	1.741 (2)	C7—C8	1.507 (3)
C2—C4	1.386 (3)	C7—H7A	0.9700
C2—H2	0.9300	C7—H7B	0.9700
C3—C5	1.379 (3)	C8—O2	1.223 (3)
C3—H3	0.9300	C8—N1	1.330 (3)
C4—C6	1.380 (3)	N1—N1i	1.390 (3)
C4—H4	0.9300	N1—H1	0.856 (10)
C5—C6	1.383 (3)	O3—H3A	0.815 (10)
C5—H5	0.9300
C2—C1—C3	120.5 (2)	O1—C6—C5	115.4 (2)
C2—C1—Cl1	120.3 (2)	C4—C6—C5	119.9 (2)
C3—C1—Cl1	119.2 (2)	O1—C7—C8	111.02 (18)
C1—C2—C4	120.0 (2)	O1—C7—H7A	109.4
C1—C2—H2	120.0	C8—C7—H7A	109.4
C4—C2—H2	120.0	O1—C7—H7B	109.4
C1—C3—C5	120.1 (2)	C8—C7—H7B	109.4
C1—C3—H3	120.0	H7A—C7—H7B	108.0
C5—C3—H3	120.0	O2—C8—N1	124.5 (2)
C6—C4—C2	119.8 (2)	O2—C8—C7	118.1 (2)
C6—C4—H4	120.1	N1—C8—C7	117.39 (19)
C2—C4—H4	120.1	C6—O1—C7	116.86 (17)
C3—C5—C6	119.7 (2)	C8—N1—N1i	119.77 (17)
C3—C5—H5	120.1	C8—N1—H1	120 (2)
C6—C5—H5	120.1	N1i—N1—H1	119 (2)
O1—C6—C4	124.7 (2)
C3—C1—C2—C4	−2.1 (4)	C3—C5—C6—C4	−1.7 (4)
Cl1—C1—C2—C4	178.4 (2)	O1—C7—C8—O2	−173.5 (2)
C2—C1—C3—C5	1.8 (4)	O1—C7—C8—N1	6.8 (3)
Cl1—C1—C3—C5	−178.6 (2)	C4—C6—O1—C7	−0.3 (3)
C1—C2—C4—C6	0.5 (4)	C5—C6—O1—C7	179.0 (2)
C1—C3—C5—C6	0.1 (4)	C8—C7—O1—C6	175.62 (18)
C2—C4—C6—O1	−179.4 (2)	O2—C8—N1—N1i	−4.2 (4)
C2—C4—C6—C5	1.4 (4)	C7—C8—N1—N1i	175.4 (2)
C3—C5—C6—O1	179.0 (2)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ii	0.93	2.47	3.382 (3)	166
O3—H3A···O2ii	0.82 (1)	1.96 (1)	2.765 (2)	169 (4)
N1—H1···O3	0.86 (1)	2.12 (2)	2.911 (3)	153 (3)
N1—H1···O1	0.86 (1)	2.26 (3)	2.633 (2)	107 (2)
C7—H7···Cg1iii	0.97	2.76	3.592 (1)	144

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
C5—H5⋯O2i	0.93	2.47	3.382 (3)	166
O3—H3A⋯O2i	0.82 (1)	1.96 (1)	2.765 (2)	169 (4)
N1—H1⋯O3	0.86 (1)	2.12 (2)	2.911 (3)	153 (3)
N1—H1⋯O1	0.86 (1)	2.26 (3)	2.633 (2)	107 (2)
C7—H7⋯Cg1ii	0.97	2.76	3.592 (1)	144

Symmetry codes: (i) ; (ii) .