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

The mol-ecule of the title compound, C(18)H(19)N(3)O(5), adopts a curved arrangement with the terminal benzene rings lying to the same side. The hydroxyl-benzene ring is close to coplanar with the adjacent hydrazine residue [dihedral angle = 11.14 (12)°], an observation which correlates with the presence of an intra-molecular O-H⋯N hydrogen bond. The benzyl ring forms a dihedral angle of 50.84 (13)° with the adjacent carbamate group. A twist in the mol-ecule, at the chiral C atom, is reflected in the dihedral angle of 80.21 (12)° formed between the amide residues. In the crystal, two-dimensional arrays in the ac plane are mediated by O-H⋯O and N-H⋯O hydrogen bonds.

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: Pinheiro et al. (2010 ▶, 2011a ▶,b ▶); de Souza et al. (2010 ▶, 2011 ▶); Howie et al. (2011 ▶).

Experimental

Crystal data

C18H19N3O5

M = 357.36

Monoclinic,

a = 5.0338 (5) Å

b = 31.357 (3) Å

c = 5.5882 (6) Å

β = 97.890 (3)°

V = 873.72 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 120 K

0.25 × 0.05 × 0.02 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.654, T max = 0.746

8786 measured reflections

2034 independent reflections

1485 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.098

S = 1.06

2034 reflections

247 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.20 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/S1600536811025128/hb5935sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025128/hb5935Isup2.hkl

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

C18H19N3O5	F(000) = 376
Mr = 357.36	Dx = 1.358 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 11033 reflections
a = 5.0338 (5) Å	θ = 2.9–27.5°
b = 31.357 (3) Å	µ = 0.10 mm−1
c = 5.5882 (6) Å	T = 120 K
β = 97.890 (3)°	Lath, colourless
V = 873.72 (16) Å3	0.25 × 0.05 × 0.02 mm
Z = 2

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	2034 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1485 reflections with I > 2σ(I)
graphite	Rint = 0.066
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.7°
φ & ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −40→40
Tmin = 0.654, Tmax = 0.746	l = −7→7
8786 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0303P)2 + 0.1614P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2034 reflections	Δρmax = 0.17 e Å−3
247 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

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	0.7558 (5)	0.24963 (8)	0.4299 (5)	0.0409 (7)
H1O	0.629 (9)	0.2299 (15)	0.440 (9)	0.061*
O2	0.2652 (5)	0.16299 (9)	0.6800 (5)	0.0427 (7)
O3	−0.2389 (5)	0.15356 (10)	0.8847 (5)	0.0443 (7)
H3O	−0.401 (10)	0.1591 (16)	0.838 (8)	0.066*
O4	−0.5493 (5)	0.07490 (8)	0.2844 (5)	0.0404 (7)
O5	−0.2450 (4)	0.03271 (7)	0.1329 (4)	0.0303 (6)
N1	0.3164 (6)	0.20615 (9)	0.2693 (6)	0.0343 (7)
N2	0.1183 (6)	0.17580 (9)	0.2843 (6)	0.0331 (7)
H2N	−0.011 (8)	0.1717 (13)	0.159 (7)	0.040*
N3	−0.1010 (6)	0.08812 (9)	0.3608 (5)	0.0274 (7)
H3N	0.069 (7)	0.0788 (11)	0.327 (6)	0.033*
C1	0.4747 (7)	0.26400 (11)	0.0505 (7)	0.0353 (9)
C2	0.6973 (7)	0.27309 (12)	0.2247 (8)	0.0366 (9)
C3	0.8652 (8)	0.30728 (12)	0.1904 (8)	0.0412 (9)
H3	1.0135	0.3136	0.3093	0.049*
C4	0.8165 (9)	0.33195 (13)	−0.0161 (8)	0.0472 (11)
H4	0.9325	0.3551	−0.0386	0.057*
C5	0.5994 (9)	0.32322 (14)	−0.1910 (8)	0.0506 (11)
H5	0.5663	0.3403	−0.3322	0.061*
C6	0.4311 (8)	0.28924 (13)	−0.1577 (8)	0.0439 (10)
H6	0.2841	0.2830	−0.2783	0.053*
C7	0.2850 (7)	0.22982 (12)	0.0788 (8)	0.0366 (9)
H7	0.1376	0.2250	−0.0437	0.044*
C8	0.1053 (6)	0.15684 (11)	0.4959 (6)	0.0304 (8)
C9	−0.1351 (7)	0.12663 (11)	0.4999 (6)	0.0287 (8)
H9	−0.2995	0.1417	0.4215	0.034*
C10	−0.1744 (7)	0.11639 (12)	0.7568 (7)	0.0367 (9)
H10A	−0.3207	0.0953	0.7555	0.044*
H10B	−0.0082	0.1035	0.8416	0.044*
C11	−0.3170 (7)	0.06639 (11)	0.2608 (6)	0.0292 (8)
C12	−0.4669 (8)	0.00648 (12)	0.0233 (8)	0.0430 (10)
H12A	−0.6019	0.0244	−0.0757	0.052*
H12B	−0.5545	−0.0076	0.1503	0.052*
C13	−0.3575 (7)	−0.02651 (11)	−0.1330 (7)	0.0334 (9)
C14	−0.1860 (8)	−0.01563 (12)	−0.2975 (7)	0.0384 (9)
H14	−0.1289	0.0131	−0.3075	0.046*
C15	−0.0973 (9)	−0.04597 (13)	−0.4467 (7)	0.0451 (10)
H15	0.0198	−0.0380	−0.5587	0.054*
C16	−0.1781 (8)	−0.08796 (12)	−0.4336 (7)	0.0435 (10)
H16	−0.1178	−0.1089	−0.5368	0.052*
C17	−0.3479 (8)	−0.09931 (13)	−0.2687 (7)	0.0445 (10)
H17	−0.4039	−0.1281	−0.2588	0.053*
C18	−0.4360 (8)	−0.06899 (12)	−0.1191 (7)	0.0414 (10)
H18	−0.5510	−0.0771	−0.0057	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0346 (15)	0.0338 (15)	0.0538 (17)	−0.0029 (12)	0.0040 (13)	0.0000 (14)
O2	0.0275 (13)	0.0537 (18)	0.0434 (15)	0.0004 (12)	−0.0074 (12)	−0.0141 (13)
O3	0.0277 (13)	0.0647 (19)	0.0378 (15)	0.0139 (14)	−0.0050 (11)	−0.0248 (14)
O4	0.0199 (12)	0.0454 (16)	0.0569 (17)	−0.0006 (11)	0.0091 (12)	−0.0179 (14)
O5	0.0221 (12)	0.0292 (14)	0.0398 (14)	−0.0031 (10)	0.0048 (11)	−0.0104 (11)
N1	0.0247 (15)	0.0287 (16)	0.049 (2)	−0.0013 (13)	0.0051 (14)	−0.0106 (16)
N2	0.0261 (16)	0.0280 (16)	0.044 (2)	−0.0023 (13)	0.0009 (14)	−0.0070 (14)
N3	0.0178 (14)	0.0290 (16)	0.0353 (16)	0.0022 (12)	0.0032 (13)	−0.0097 (13)
C1	0.035 (2)	0.030 (2)	0.044 (2)	0.0020 (16)	0.0139 (18)	−0.0081 (17)
C2	0.033 (2)	0.0279 (19)	0.051 (2)	0.0053 (16)	0.0136 (18)	−0.0052 (19)
C3	0.034 (2)	0.030 (2)	0.060 (3)	−0.0013 (18)	0.0095 (19)	−0.005 (2)
C4	0.044 (2)	0.033 (2)	0.069 (3)	0.0024 (18)	0.023 (2)	−0.005 (2)
C5	0.056 (3)	0.042 (2)	0.057 (3)	0.007 (2)	0.021 (2)	0.001 (2)
C6	0.047 (2)	0.042 (2)	0.045 (2)	0.0035 (19)	0.014 (2)	−0.0073 (19)
C7	0.032 (2)	0.030 (2)	0.049 (2)	0.0038 (15)	0.0080 (18)	−0.0136 (19)
C8	0.0210 (17)	0.0295 (19)	0.039 (2)	0.0042 (15)	−0.0030 (15)	−0.0110 (17)
C9	0.0230 (17)	0.0299 (19)	0.0321 (19)	0.0057 (15)	−0.0003 (15)	−0.0035 (15)
C10	0.0291 (19)	0.046 (2)	0.034 (2)	0.0114 (17)	0.0007 (16)	−0.0069 (18)
C11	0.0248 (19)	0.0317 (19)	0.0318 (19)	−0.0024 (15)	0.0066 (15)	−0.0072 (16)
C12	0.028 (2)	0.040 (2)	0.061 (3)	−0.0096 (17)	0.006 (2)	−0.022 (2)
C13	0.0280 (19)	0.029 (2)	0.042 (2)	−0.0010 (15)	0.0006 (17)	−0.0080 (17)
C14	0.042 (2)	0.030 (2)	0.042 (2)	−0.0026 (17)	0.0029 (18)	−0.0054 (17)
C15	0.059 (3)	0.037 (2)	0.041 (2)	−0.003 (2)	0.013 (2)	−0.0047 (19)
C16	0.057 (3)	0.031 (2)	0.043 (2)	0.0049 (18)	0.006 (2)	−0.0081 (19)
C17	0.052 (2)	0.029 (2)	0.053 (3)	−0.0063 (19)	0.010 (2)	−0.0085 (19)
C18	0.042 (2)	0.039 (2)	0.045 (2)	−0.0071 (18)	0.0127 (19)	−0.0061 (19)

O1—C2	1.360 (5)	C5—C6	1.389 (6)
O1—H1O	0.89 (5)	C5—H5	0.9500
O2—C8	1.231 (4)	C6—H6	0.9500
O3—C10	1.428 (4)	C7—H7	0.9500
O3—H3O	0.84 (5)	C8—C9	1.540 (5)
O4—C11	1.224 (4)	C9—C10	1.510 (5)
O5—C11	1.352 (4)	C9—H9	1.0000
O5—C12	1.453 (4)	C10—H10A	0.9900
N1—C7	1.290 (5)	C10—H10B	0.9900
N1—N2	1.389 (4)	C12—C13	1.506 (5)
N2—C8	1.333 (5)	C12—H12A	0.9900
N2—H2N	0.90 (4)	C12—H12B	0.9900
N3—C11	1.339 (4)	C13—C14	1.387 (6)
N3—C9	1.459 (4)	C13—C18	1.395 (5)
N3—H3N	0.95 (4)	C14—C15	1.379 (5)
C1—C6	1.400 (5)	C14—H14	0.9500
C1—C2	1.409 (5)	C15—C16	1.383 (6)
C1—C7	1.458 (5)	C15—H15	0.9500
C2—C3	1.394 (5)	C16—C17	1.387 (6)
C3—C4	1.383 (6)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.379 (5)
C4—C5	1.390 (6)	C17—H17	0.9500
C4—H4	0.9500	C18—H18	0.9500
C2—O1—H1O	111 (3)	N3—C9—H9	108.0
C10—O3—H3O	107 (3)	C10—C9—H9	108.0
C11—O5—C12	114.7 (2)	C8—C9—H9	108.0
C7—N1—N2	115.9 (3)	O3—C10—C9	111.8 (3)
C8—N2—N1	118.8 (3)	O3—C10—H10A	109.3
C8—N2—H2N	121 (3)	C9—C10—H10A	109.3
N1—N2—H2N	120 (3)	O3—C10—H10B	109.3
C11—N3—C9	119.7 (3)	C9—C10—H10B	109.3
C11—N3—H3N	118 (2)	H10A—C10—H10B	107.9
C9—N3—H3N	122 (2)	O4—C11—N3	125.3 (3)
C6—C1—C2	118.6 (3)	O4—C11—O5	123.8 (3)
C6—C1—C7	118.4 (4)	N3—C11—O5	110.9 (3)
C2—C1—C7	123.0 (4)	O5—C12—C13	108.2 (3)
O1—C2—C3	117.8 (4)	O5—C12—H12A	110.1
O1—C2—C1	122.2 (3)	C13—C12—H12A	110.1
C3—C2—C1	120.0 (4)	O5—C12—H12B	110.1
C4—C3—C2	120.2 (4)	C13—C12—H12B	110.1
C4—C3—H3	119.9	H12A—C12—H12B	108.4
C2—C3—H3	119.9	C14—C13—C18	118.6 (3)
C3—C4—C5	120.6 (4)	C14—C13—C12	121.7 (3)
C3—C4—H4	119.7	C18—C13—C12	119.7 (4)
C5—C4—H4	119.7	C15—C14—C13	120.9 (4)
C4—C5—C6	119.5 (4)	C15—C14—H14	119.5
C4—C5—H5	120.3	C13—C14—H14	119.5
C6—C5—H5	120.3	C14—C15—C16	120.2 (4)
C5—C6—C1	121.1 (4)	C14—C15—H15	119.9
C5—C6—H6	119.5	C16—C15—H15	119.9
C1—C6—H6	119.5	C15—C16—C17	119.5 (4)
N1—C7—C1	120.3 (3)	C15—C16—H16	120.3
N1—C7—H7	119.8	C17—C16—H16	120.3
C1—C7—H7	119.8	C18—C17—C16	120.3 (4)
O2—C8—N2	124.4 (3)	C18—C17—H17	119.8
O2—C8—C9	120.6 (3)	C16—C17—H17	119.8
N2—C8—C9	114.9 (3)	C17—C18—C13	120.5 (4)
N3—C9—C10	111.8 (3)	C17—C18—H18	119.7
N3—C9—C8	110.6 (3)	C13—C18—H18	119.7
C10—C9—C8	110.5 (3)
C7—N1—N2—C8	−165.5 (3)	N2—C8—C9—N3	71.1 (4)
C6—C1—C2—O1	−178.9 (3)	O2—C8—C9—C10	13.6 (4)
C7—C1—C2—O1	2.0 (5)	N2—C8—C9—C10	−164.7 (3)
C6—C1—C2—C3	1.5 (5)	N3—C9—C10—O3	−173.2 (3)
C7—C1—C2—C3	−177.6 (3)	C8—C9—C10—O3	63.2 (3)
O1—C2—C3—C4	179.4 (3)	C9—N3—C11—O4	−3.6 (5)
C1—C2—C3—C4	−1.0 (5)	C9—N3—C11—O5	177.9 (3)
C2—C3—C4—C5	0.4 (6)	C12—O5—C11—O4	−0.2 (5)
C3—C4—C5—C6	−0.3 (6)	C12—O5—C11—N3	178.3 (3)
C4—C5—C6—C1	0.8 (6)	C11—O5—C12—C13	174.0 (3)
C2—C1—C6—C5	−1.4 (5)	O5—C12—C13—C14	−48.4 (5)
C7—C1—C6—C5	177.7 (3)	O5—C12—C13—C18	133.7 (4)
N2—N1—C7—C1	177.1 (3)	C18—C13—C14—C15	0.9 (6)
C6—C1—C7—N1	−179.2 (3)	C12—C13—C14—C15	−177.1 (4)
C2—C1—C7—N1	−0.2 (5)	C13—C14—C15—C16	−0.2 (6)
N1—N2—C8—O2	−3.2 (5)	C14—C15—C16—C17	−0.3 (6)
N1—N2—C8—C9	174.9 (3)	C15—C16—C17—C18	0.1 (7)
C11—N3—C9—C10	82.9 (4)	C16—C17—C18—C13	0.6 (6)
C11—N3—C9—C8	−153.6 (3)	C14—C13—C18—C17	−1.0 (6)
O2—C8—C9—N3	−110.7 (4)	C12—C13—C18—C17	177.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.90 (5)	1.88 (5)	2.648 (4)	143 (4)
O3—H3o···O2i	0.84 (5)	1.79 (5)	2.616 (4)	167 (5)
N2—H2n···O3ii	0.90 (4)	1.87 (4)	2.758 (4)	168 (4)
N3—H3n···O4iii	0.95 (4)	1.97 (4)	2.897 (4)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.90 (5)	1.88 (5)	2.648 (4)	143 (4)
O3—H3o⋯O2i	0.84 (5)	1.79 (5)	2.616 (4)	167 (5)
N2—H2n⋯O3ii	0.90 (4)	1.87 (4)	2.758 (4)	168 (4)
N3—H3n⋯O4iii	0.95 (4)	1.97 (4)	2.897 (4)	165 (3)

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