Benzyl N-(1-{N'-[(E)-2,3-dihy-droxy-benzyl-idene]hydrazinecarbon-yl}-2-hy-droxy-eth-yl)carbamate dihydrate.

The organic mol-ecule in the title dihydrate, C(18)H(19)N(3)O(6)·2H(2)O, adopts a twisted U-shape with the major twists evident about the chiral C atom [the C-N-C-C torsion angle is -88.2 (4) °] and about the oxygen-benzyl bond [C-O-C-C = 74.2 (4) °]. The conformation about the imine bond [1.290 (4) Å] is E and an intra-molecular O-H⋯N hydrogen bond helps to establish the near coplanarity of the hy-droxy-benzene and hydrazine groups. The crystal packing features O-H⋯O and N-H⋯O hydrogen bonds, leading to two-dimensional supra-molecular arrays in the ab plane with weak C-H⋯π connections between the arrays.

Related literature

For background to the use of l-serine derivatives in anti-tumour therapy, see: Jiao et al. (2009 ▶); Yakura et al. (2007 ▶). For background to N-acyl­hydrazone derivatives from l-serine for anti-tumour testing, see: de Souza et al. (2010 ▶, 2011 ▶); Pinheiro et al. (2010 ▶, 2011 ▶); Howie et al. (2011 ▶); Tiekink et al. (2011 ▶); Wardell et al. (2011 ▶).

Experimental

Crystal data

C18H19N3O6·2H2O

M = 409.39

Orthorhombic,

a = 4.7570 (2) Å

b = 13.1011 (4) Å

c = 30.5511 (9) Å

V = 1904.00 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 120 K

0.18 × 0.12 × 0.10 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.887, T max = 1.000

12958 measured reflections

2560 independent reflections

1984 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.114

S = 1.11

2560 reflections

289 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.26 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029370/hb6326sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029370/hb6326Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029370/hb6326Isup3.cml

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

C18H19N3O6·2H2O	F(000) = 864
Mr = 409.39	Dx = 1.428 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9601 reflections
a = 4.7570 (2) Å	θ = 2.9–27.5°
b = 13.1011 (4) Å	µ = 0.11 mm−1
c = 30.5511 (9) Å	T = 120 K
V = 1904.00 (11) Å3	Block, pale-brown
Z = 4	0.18 × 0.12 × 0.10 mm

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	2560 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1984 reflections with I > 2σ(I)
graphite	Rint = 0.074
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.1°
φ and ω scans	h = −6→5
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −17→16
Tmin = 0.887, Tmax = 1.000	l = −37→39
12958 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.034P)2 + 0.4778P] where P = (Fo2 + 2Fc2)/3
2560 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.23 e Å−3
9 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.5296 (5)	0.14889 (15)	0.34576 (7)	0.0256 (5)
H1O	0.435 (7)	0.2000 (19)	0.3378 (10)	0.038*
O2	0.8776 (5)	0.00115 (16)	0.38088 (8)	0.0289 (6)
H2O	0.719 (4)	−0.022 (3)	0.3735 (12)	0.043*
O3	0.0260 (5)	0.33623 (15)	0.27559 (7)	0.0288 (6)
O4	0.3510 (5)	0.54140 (18)	0.23084 (7)	0.0293 (6)
H4O	0.391 (10)	0.571 (3)	0.2077 (11)	0.044*
O5	−0.3437 (5)	0.58789 (16)	0.34957 (7)	0.0246 (5)
O6	−0.0248 (5)	0.71487 (15)	0.35850 (6)	0.0249 (6)
N1	0.4021 (7)	0.34210 (18)	0.34263 (8)	0.0222 (6)
N2	0.2671 (6)	0.42717 (19)	0.32640 (8)	0.0225 (6)
H2N	0.337 (7)	0.4863 (14)	0.3341 (10)	0.027*
N3	0.0278 (6)	0.60659 (19)	0.30326 (8)	0.0218 (6)
H3N	0.172 (9)	0.642 (2)	0.2984 (10)	0.026*
C1	0.7354 (7)	0.2756 (2)	0.39369 (9)	0.0208 (7)
C2	0.7133 (7)	0.1748 (2)	0.37819 (10)	0.0204 (7)
C3	0.8820 (8)	0.0997 (2)	0.39619 (10)	0.0230 (7)
C4	1.0684 (8)	0.1236 (2)	0.42946 (10)	0.0264 (8)
H4	1.1846	0.0716	0.4414	0.032*
C5	1.0887 (9)	0.2223 (2)	0.44573 (10)	0.0283 (8)
H5	1.2161	0.2376	0.4688	0.034*
C6	0.9210 (8)	0.2979 (2)	0.42797 (9)	0.0257 (8)
H6	0.9318	0.3655	0.4391	0.031*
C7	0.5738 (8)	0.3584 (2)	0.37454 (9)	0.0228 (7)
H7	0.5949	0.4257	0.3857	0.027*
C8	0.0844 (8)	0.4187 (2)	0.29279 (9)	0.0213 (7)
C9	−0.0437 (8)	0.5184 (2)	0.27644 (9)	0.0213 (7)
H9	−0.2529	0.5109	0.2763	0.026*
C10	0.0533 (8)	0.5356 (3)	0.22979 (10)	0.0253 (8)
H10A	−0.0080	0.4785	0.2109	0.030*
H10B	−0.0269	0.5998	0.2181	0.030*
C11	−0.1316 (8)	0.6322 (2)	0.33806 (10)	0.0213 (7)
C12	−0.1522 (9)	0.7377 (2)	0.40029 (9)	0.0267 (8)
H12A	−0.3592	0.7348	0.3973	0.032*
H12B	−0.1009	0.8081	0.4090	0.032*
C13	−0.0615 (8)	0.6646 (2)	0.43599 (10)	0.0240 (7)
C14	0.1605 (8)	0.5972 (2)	0.43100 (10)	0.0286 (8)
H14	0.2612	0.5948	0.4042	0.034*
C15	0.2360 (8)	0.5330 (3)	0.46517 (10)	0.0305 (8)
H15	0.3859	0.4859	0.4613	0.037*
C16	0.0959 (9)	0.5366 (3)	0.50491 (10)	0.0299 (8)
H16	0.1499	0.4931	0.5283	0.036*
C17	−0.1231 (9)	0.6044 (3)	0.50978 (11)	0.0342 (9)
H17	−0.2201	0.6079	0.5369	0.041*
C18	−0.2039 (8)	0.6676 (3)	0.47569 (10)	0.0295 (8)
H18	−0.3573	0.7132	0.4795	0.035*
O1W	0.4103 (6)	0.91059 (18)	0.35680 (8)	0.0343 (6)
H1W	0.248 (4)	0.936 (3)	0.3598 (11)	0.051*
H2W	0.416 (8)	0.876 (2)	0.3336 (7)	0.051*
O2W	0.5751 (6)	0.28389 (19)	0.22018 (7)	0.0310 (6)
H3W	0.420 (4)	0.282 (3)	0.2339 (10)	0.047*
H4W	0.695 (6)	0.303 (3)	0.2392 (9)	0.047*

	U11	U22	U33	U12	U13	U23
O1	0.0249 (15)	0.0216 (11)	0.0302 (12)	0.0024 (10)	−0.0065 (11)	−0.0023 (10)
O2	0.0241 (14)	0.0196 (12)	0.0430 (13)	−0.0005 (12)	−0.0046 (12)	0.0010 (10)
O3	0.0296 (15)	0.0218 (11)	0.0350 (12)	−0.0035 (12)	−0.0039 (12)	−0.0053 (10)
O4	0.0240 (14)	0.0372 (14)	0.0268 (12)	−0.0026 (12)	0.0030 (12)	0.0055 (11)
O5	0.0228 (14)	0.0230 (11)	0.0280 (11)	−0.0033 (11)	0.0013 (11)	−0.0011 (10)
O6	0.0295 (15)	0.0199 (11)	0.0254 (11)	−0.0061 (11)	0.0002 (11)	−0.0010 (9)
N1	0.0241 (16)	0.0187 (13)	0.0237 (13)	0.0026 (13)	−0.0005 (13)	0.0024 (11)
N2	0.0248 (17)	0.0155 (13)	0.0273 (13)	0.0008 (13)	−0.0066 (13)	0.0003 (11)
N3	0.0163 (16)	0.0215 (14)	0.0276 (14)	−0.0010 (13)	−0.0002 (13)	0.0001 (11)
C1	0.0201 (18)	0.0213 (16)	0.0210 (14)	−0.0004 (15)	0.0020 (15)	0.0014 (13)
C2	0.0199 (18)	0.0199 (16)	0.0214 (15)	−0.0011 (15)	0.0019 (15)	−0.0001 (13)
C3	0.0212 (19)	0.0184 (15)	0.0293 (16)	0.0006 (15)	0.0038 (15)	0.0021 (13)
C4	0.0189 (19)	0.0291 (17)	0.0314 (17)	0.0024 (16)	−0.0020 (16)	0.0060 (14)
C5	0.027 (2)	0.0305 (17)	0.0274 (16)	−0.0039 (18)	−0.0052 (16)	0.0053 (14)
C6	0.026 (2)	0.0254 (16)	0.0255 (15)	−0.0048 (17)	0.0005 (16)	0.0014 (14)
C7	0.0238 (19)	0.0212 (16)	0.0235 (15)	0.0002 (15)	0.0015 (16)	0.0008 (13)
C8	0.0195 (18)	0.0248 (16)	0.0195 (14)	−0.0026 (16)	0.0002 (14)	−0.0012 (13)
C9	0.0191 (18)	0.0201 (14)	0.0248 (15)	0.0008 (15)	0.0003 (15)	−0.0009 (12)
C10	0.023 (2)	0.0295 (17)	0.0232 (15)	−0.0018 (16)	−0.0027 (16)	0.0013 (14)
C11	0.024 (2)	0.0158 (14)	0.0240 (16)	−0.0003 (15)	−0.0037 (15)	0.0018 (12)
C12	0.034 (2)	0.0211 (16)	0.0247 (15)	−0.0012 (16)	0.0032 (16)	−0.0017 (13)
C13	0.0264 (19)	0.0186 (15)	0.0269 (16)	−0.0055 (16)	−0.0033 (15)	−0.0019 (13)
C14	0.026 (2)	0.0315 (18)	0.0279 (17)	−0.0005 (17)	−0.0006 (16)	−0.0013 (15)
C15	0.026 (2)	0.0289 (18)	0.0366 (19)	0.0015 (17)	−0.0031 (17)	0.0013 (16)
C16	0.030 (2)	0.0300 (18)	0.0299 (17)	−0.0053 (18)	−0.0082 (18)	0.0059 (15)
C17	0.042 (2)	0.0332 (19)	0.0276 (17)	−0.003 (2)	0.0038 (18)	−0.0001 (15)
C18	0.029 (2)	0.0257 (17)	0.0337 (18)	0.0031 (17)	0.0026 (17)	−0.0021 (15)
O1W	0.0290 (15)	0.0288 (13)	0.0451 (14)	0.0034 (13)	−0.0043 (13)	−0.0095 (11)
O2W	0.0283 (15)	0.0302 (12)	0.0346 (13)	0.0016 (14)	−0.0016 (12)	−0.0039 (11)

O1—C2	1.364 (4)	C6—H6	0.9500
O1—H1O	0.842 (10)	C7—H7	0.9500
O2—C3	1.374 (4)	C8—C9	1.526 (4)
O2—H2O	0.843 (10)	C9—C10	1.515 (4)
O3—C8	1.233 (3)	C9—H9	1.0000
O4—C10	1.418 (4)	C10—H10A	0.9900
O4—H4O	0.83 (4)	C10—H10B	0.9900
O5—C11	1.216 (4)	C12—C13	1.515 (4)
O6—C11	1.350 (4)	C12—H12A	0.9900
O6—C12	1.445 (3)	C12—H12B	0.9900
N1—C7	1.290 (4)	C13—C14	1.385 (5)
N1—N2	1.379 (3)	C13—C18	1.390 (4)
N2—C8	1.350 (4)	C14—C15	1.388 (4)
N2—H2N	0.875 (10)	C14—H14	0.9500
N3—C11	1.349 (4)	C15—C16	1.386 (5)
N3—C9	1.456 (4)	C15—H15	0.9500
N3—H3N	0.84 (4)	C16—C17	1.378 (5)
C1—C6	1.401 (4)	C16—H16	0.9500
C1—C2	1.407 (4)	C17—C18	1.385 (5)
C1—C7	1.453 (4)	C17—H17	0.9500
C2—C3	1.383 (4)	C18—H18	0.9500
C3—C4	1.385 (5)	O1W—H1W	0.851 (10)
C4—C5	1.388 (4)	O1W—H2W	0.845 (10)
C4—H4	0.9500	O2W—H3W	0.848 (10)
C5—C6	1.383 (5)	O2W—H4W	0.852 (10)
C5—H5	0.9500
C2—O1—H1O	111 (3)	N3—C9—H9	108.3
C3—O2—H2O	116 (3)	C10—C9—H9	108.3
C10—O4—H4O	104 (3)	C8—C9—H9	108.3
C11—O6—C12	114.7 (3)	O4—C10—C9	106.9 (3)
C7—N1—N2	115.6 (2)	O4—C10—H10A	110.3
C8—N2—N1	120.5 (2)	C9—C10—H10A	110.3
C8—N2—H2N	121 (2)	O4—C10—H10B	110.3
N1—N2—H2N	116 (2)	C9—C10—H10B	110.3
C11—N3—C9	120.6 (3)	H10A—C10—H10B	108.6
C11—N3—H3N	118 (2)	O5—C11—N3	125.2 (3)
C9—N3—H3N	122 (2)	O5—C11—O6	124.2 (3)
C6—C1—C2	119.6 (3)	N3—C11—O6	110.7 (3)
C6—C1—C7	118.6 (3)	O6—C12—C13	112.7 (3)
C2—C1—C7	121.8 (3)	O6—C12—H12A	109.1
O1—C2—C3	118.9 (3)	C13—C12—H12A	109.1
O1—C2—C1	121.7 (3)	O6—C12—H12B	109.1
C3—C2—C1	119.4 (3)	C13—C12—H12B	109.1
O2—C3—C4	118.2 (3)	H12A—C12—H12B	107.8
O2—C3—C2	121.6 (3)	C14—C13—C18	119.1 (3)
C4—C3—C2	120.2 (3)	C14—C13—C12	122.8 (3)
C3—C4—C5	121.2 (3)	C18—C13—C12	118.1 (3)
C3—C4—H4	119.4	C13—C14—C15	120.1 (3)
C5—C4—H4	119.4	C13—C14—H14	120.0
C6—C5—C4	119.1 (3)	C15—C14—H14	120.0
C6—C5—H5	120.4	C16—C15—C14	120.9 (3)
C4—C5—H5	120.4	C16—C15—H15	119.5
C5—C6—C1	120.5 (3)	C14—C15—H15	119.5
C5—C6—H6	119.7	C17—C16—C15	118.7 (3)
C1—C6—H6	119.7	C17—C16—H16	120.6
N1—C7—C1	121.0 (3)	C15—C16—H16	120.6
N1—C7—H7	119.5	C16—C17—C18	121.0 (3)
C1—C7—H7	119.5	C16—C17—H17	119.5
O3—C8—N2	122.8 (3)	C18—C17—H17	119.5
O3—C8—C9	121.4 (3)	C17—C18—C13	120.3 (3)
N2—C8—C9	115.8 (3)	C17—C18—H18	119.9
N3—C9—C10	109.9 (3)	C13—C18—H18	119.9
N3—C9—C8	113.7 (2)	H1W—O1W—H2W	109 (2)
C10—C9—C8	108.3 (3)	H3W—O2W—H4W	105 (2)
C7—N1—N2—C8	179.6 (3)	O3—C8—C9—N3	174.4 (3)
C6—C1—C2—O1	178.0 (3)	N2—C8—C9—N3	−6.7 (4)
C7—C1—C2—O1	−3.1 (5)	O3—C8—C9—C10	−63.2 (4)
C6—C1—C2—C3	−2.0 (5)	N2—C8—C9—C10	115.7 (3)
C7—C1—C2—C3	176.9 (3)	N3—C9—C10—O4	64.5 (3)
O1—C2—C3—O2	3.0 (5)	C8—C9—C10—O4	−60.2 (3)
C1—C2—C3—O2	−177.0 (3)	C9—N3—C11—O5	−1.4 (5)
O1—C2—C3—C4	−179.4 (3)	C9—N3—C11—O6	179.0 (3)
C1—C2—C3—C4	0.7 (5)	C12—O6—C11—O5	10.5 (4)
O2—C3—C4—C5	178.4 (3)	C12—O6—C11—N3	−169.9 (3)
C2—C3—C4—C5	0.7 (5)	C11—O6—C12—C13	74.2 (4)
C3—C4—C5—C6	−0.6 (6)	O6—C12—C13—C14	12.3 (5)
C4—C5—C6—C1	−0.7 (5)	O6—C12—C13—C18	−169.4 (3)
C2—C1—C6—C5	2.0 (5)	C18—C13—C14—C15	0.8 (5)
C7—C1—C6—C5	−176.9 (3)	C12—C13—C14—C15	179.1 (3)
N2—N1—C7—C1	−178.2 (3)	C13—C14—C15—C16	−1.4 (5)
C6—C1—C7—N1	179.3 (3)	C14—C15—C16—C17	0.8 (5)
C2—C1—C7—N1	0.4 (5)	C15—C16—C17—C18	0.4 (5)
N1—N2—C8—O3	1.2 (5)	C16—C17—C18—C13	−1.0 (5)
N1—N2—C8—C9	−177.7 (3)	C14—C13—C18—C17	0.4 (5)
C11—N3—C9—C10	150.3 (3)	C12—C13—C18—C17	−178.0 (3)
C11—N3—C9—C8	−88.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.84 (2)	1.88 (2)	2.604 (3)	143 (3)
O2—H2o···O1wi	0.84 (2)	1.79 (2)	2.625 (3)	170 (3)
O4—H4o···O1ii	0.82 (3)	1.97 (3)	2.791 (3)	176 (3)
O1w—H1w···O2iii	0.85 (2)	2.05 (2)	2.894 (3)	169 (3)
O1w—H2w···O2wii	0.84 (2)	2.04 (2)	2.879 (3)	176 (2)
O2w—H3w···O3	0.85 (2)	2.38 (2)	3.188 (3)	160 (3)
O2w—H4w···O3iv	0.86 (3)	1.97 (2)	2.818 (3)	168 (3)
N2—H2n···O5iv	0.874 (19)	2.08 (2)	2.892 (3)	154 (2)
N2—H2n···N3	0.874 (19)	2.34 (2)	2.705 (3)	106 (2)
N3—H3n···O2wii	0.85 (3)	2.28 (3)	3.078 (3)	157 (3)
C18—H18···Cg1v	0.95	2.94	3.700 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.84 (2)	1.88 (2)	2.604 (3)	143 (3)
O2—H2o⋯O1wi	0.84 (2)	1.79 (2)	2.625 (3)	170 (3)
O4—H4o⋯O1ii	0.82 (3)	1.97 (3)	2.791 (3)	176 (3)
O1w—H1w⋯O2iii	0.85 (2)	2.05 (2)	2.894 (3)	169 (3)
O1w—H2w⋯O2wii	0.84 (2)	2.04 (2)	2.879 (3)	176 (2)
O2w—H3w⋯O3	0.85 (2)	2.38 (2)	3.188 (3)	160 (3)
O2w—H4w⋯O3iv	0.86 (3)	1.97 (2)	2.818 (3)	168 (3)
N2—H2n⋯O5iv	0.87 (2)	2.08 (2)	2.892 (3)	154 (2)
N2—H2n⋯N3	0.87 (2)	2.34 (2)	2.705 (3)	106 (2)
N3—H3n⋯O2wii	0.85 (3)	2.28 (3)	3.078 (3)	157 (3)
C18—H18⋯Cg1v	0.95	2.94	3.700 (3)	138

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