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

The carbamate and hydrazone groups in the title compound, C(18)H(18)N(4)O(6), are approximately orthogonal [dihedral angle = 83.3 (4)°], and the carbonyl groups are effectively anti [O=C⋯C=O torsion angle = -116.2 (7)°]. The conformation about the imine bond [1.295 (11) Å] is E. The crystal packing is dominated by O-H⋯O and N-H⋯O hydrogen bonding, which leads to two-dimensional arrays in the ab plane.

Related literature

For background to the anti-tumour potential of l-serine derivatives, see: Jiao et al. (2009 ▶); Yakura et al. (2007 ▶); Takahashi et al. (1988 ▶); Sin et al. (1998 ▶). For background of the anti-tumour potential of N-acyl­hydrazone l-serine derivatives, see: Rollas & Küçükgüzel (2007 ▶); Terzioğlu & Gürsoy (2003 ▶).

Experimental

Crystal data

C18H18N4O6

M = 386.36

Triclinic,

a = 4.6675 (7) Å

b = 5.7001 (7) Å

c = 16.645 (3) Å

α = 90.457 (9)°

β = 92.087 (7)°

γ = 97.319 (9)°

V = 438.90 (11) Å3

Z = 1

Mo Kα radiation

μ = 0.11 mm−1

T = 120 K

0.20 × 0.07 × 0.01 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.624, T max = 1.000

7083 measured reflections

1791 independent reflections

1243 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.089

wR(F 2) = 0.190

S = 1.14

1791 reflections

262 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.32 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 datablocks global, I. DOI: 10.1107/S1600536810027273/zs2049sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027273/zs2049Isup2.hkl

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

C18H18N4O6	Z = 1
Mr = 386.36	F(000) = 202
Triclinic, P1	Dx = 1.462 Mg m−3
Hall symbol: P 1	Melting point = 428–429 K
a = 4.6675 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.7001 (7) Å	Cell parameters from 18416 reflections
c = 16.645 (3) Å	θ = 2.9–27.5°
α = 90.457 (9)°	µ = 0.11 mm−1
β = 92.087 (7)°	T = 120 K
γ = 97.319 (9)°	Plate, colourless
V = 438.90 (11) Å3	0.20 × 0.07 × 0.01 mm

Nonius KappaCCD area-detector diffractometer	1791 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1243 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.093
Detector resolution: 9.091 pixels mm-1	θmax = 26.5°, θmin = 3.6°
φ and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −6→7
Tmin = 0.624, Tmax = 1.000	l = −20→20
7083 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)] = 0.089	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.037P)2 + 1.2849P] where P = (Fo2 + 2Fc2)/3
1791 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.39 e Å−3
6 restraints	Δρmin = −0.32 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	0.2947 (12)	0.8892 (10)	0.3007 (4)	0.0270 (14)
O2	−0.0905 (13)	0.6386 (10)	0.2534 (4)	0.0294 (15)
O3	−0.4518 (12)	1.3215 (11)	0.1633 (4)	0.0297 (15)
H3O	−0.350 (19)	1.374 (18)	0.204 (4)	0.045*
O4	0.1745 (14)	0.8327 (12)	0.0625 (4)	0.0395 (17)
O5	−0.6765 (15)	0.6119 (12)	−0.2286 (4)	0.0427 (19)
O6	−0.6271 (16)	0.4575 (13)	−0.3452 (4)	0.0450 (19)
N1	0.0112 (16)	1.0119 (13)	0.2030 (5)	0.0267 (17)
H1N	0.156 (13)	1.122 (12)	0.195 (6)	0.032*
N2	−0.2884 (15)	0.7320 (14)	0.0165 (5)	0.0285 (18)
H2N	−0.469 (7)	0.718 (17)	0.031 (5)	0.034*
N3	−0.1965 (16)	0.5952 (12)	−0.0441 (5)	0.0272 (18)
N4	−0.5754 (16)	0.4722 (12)	−0.2727 (5)	0.0291 (18)
C1	0.0588 (17)	0.8301 (16)	0.2530 (5)	0.024 (2)
C2	−0.2011 (19)	0.9716 (15)	0.1386 (5)	0.025 (2)
H2	−0.3785	0.8760	0.1585	0.030*
C3	−0.278 (2)	1.2117 (16)	0.1085 (5)	0.029 (2)
H3A	−0.0978	1.3188	0.1004	0.035*
H3B	−0.3842	1.1877	0.0559	0.035*
C4	−0.0811 (19)	0.8361 (14)	0.0693 (5)	0.0221 (19)
C5	−0.398 (2)	0.4987 (15)	−0.0938 (5)	0.026 (2)
H5	−0.5928	0.5308	−0.0921	0.031*
C6	−0.3011 (19)	0.3339 (14)	−0.1536 (6)	0.026 (2)
C7	−0.3789 (19)	0.3147 (14)	−0.2349 (6)	0.026 (2)
C8	−0.2776 (19)	0.1553 (16)	−0.2870 (6)	0.029 (2)
H8	−0.3347	0.1492	−0.3424	0.035*
C9	−0.092 (2)	0.0061 (16)	−0.2560 (6)	0.032 (2)
H9	−0.0215	−0.1062	−0.2902	0.039*
C10	−0.006 (2)	0.0190 (16)	−0.1754 (6)	0.031 (2)
H10	0.1263	−0.0809	−0.1548	0.038*
C11	−0.1140 (18)	0.1766 (14)	−0.1252 (5)	0.026 (2)
H11	−0.0600	0.1790	−0.0696	0.031*
C12	0.347 (2)	0.7141 (16)	0.3589 (6)	0.030 (2)
H12A	0.4009	0.5724	0.3313	0.036*
H12B	0.1691	0.6662	0.3884	0.036*
C13	0.5886 (19)	0.8140 (16)	0.4173 (6)	0.026 (2)
C14	0.737 (2)	1.0378 (16)	0.4112 (6)	0.030 (2)
H14	0.6857	1.1380	0.3691	0.035*
C15	0.958 (2)	1.1178 (18)	0.4651 (6)	0.038 (2)
H15	1.0609	1.2714	0.4596	0.045*
C16	1.031 (2)	0.9758 (18)	0.5270 (6)	0.038 (3)
H16	1.1847	1.0311	0.5642	0.045*
C17	0.881 (2)	0.7527 (18)	0.5351 (6)	0.037 (3)
H17	0.9294	0.6546	0.5781	0.045*
C18	0.659 (2)	0.6729 (16)	0.4798 (6)	0.031 (2)
H18	0.5543	0.5199	0.4853	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.024 (3)	0.030 (3)	0.027 (4)	0.003 (3)	0.002 (3)	0.012 (3)
O2	0.021 (3)	0.029 (3)	0.036 (4)	−0.002 (3)	−0.002 (3)	0.000 (3)
O3	0.023 (4)	0.035 (4)	0.032 (4)	0.003 (3)	0.003 (3)	−0.006 (3)
O4	0.022 (4)	0.049 (4)	0.047 (4)	0.003 (3)	−0.001 (3)	−0.015 (3)
O5	0.048 (5)	0.043 (4)	0.041 (4)	0.024 (4)	−0.002 (4)	−0.006 (3)
O6	0.053 (5)	0.057 (5)	0.027 (4)	0.018 (4)	−0.008 (3)	−0.001 (3)
N1	0.022 (4)	0.032 (5)	0.025 (4)	0.001 (3)	−0.002 (3)	−0.006 (3)
N2	0.016 (4)	0.038 (4)	0.032 (4)	0.003 (3)	0.003 (3)	−0.013 (4)
N3	0.026 (4)	0.024 (4)	0.033 (4)	0.003 (3)	0.003 (4)	0.000 (3)
N4	0.030 (5)	0.022 (4)	0.035 (5)	0.004 (3)	−0.004 (4)	0.005 (3)
C1	0.010 (4)	0.037 (5)	0.023 (5)	0.000 (4)	−0.005 (4)	−0.008 (4)
C2	0.018 (5)	0.028 (5)	0.028 (5)	−0.003 (4)	0.003 (4)	−0.001 (4)
C3	0.039 (6)	0.026 (5)	0.022 (5)	0.003 (4)	−0.005 (4)	−0.004 (4)
C4	0.026 (5)	0.020 (4)	0.021 (5)	0.002 (3)	0.013 (4)	0.005 (3)
C5	0.028 (5)	0.028 (5)	0.022 (5)	0.005 (4)	0.004 (4)	−0.006 (4)
C6	0.026 (5)	0.016 (4)	0.037 (6)	0.000 (4)	−0.004 (4)	−0.007 (4)
C7	0.020 (5)	0.016 (4)	0.041 (6)	−0.004 (3)	0.005 (4)	−0.001 (4)
C8	0.032 (5)	0.034 (5)	0.019 (5)	0.000 (4)	0.000 (4)	−0.011 (4)
C9	0.037 (6)	0.027 (5)	0.036 (6)	0.012 (4)	0.006 (5)	−0.013 (4)
C10	0.032 (5)	0.028 (5)	0.034 (6)	0.000 (4)	0.007 (5)	−0.010 (4)
C11	0.028 (5)	0.023 (5)	0.023 (5)	−0.005 (4)	−0.001 (4)	0.003 (4)
C12	0.031 (5)	0.025 (5)	0.033 (6)	0.005 (4)	−0.005 (4)	0.002 (4)
C13	0.023 (5)	0.030 (5)	0.025 (5)	0.005 (4)	0.011 (4)	0.000 (4)
C14	0.030 (5)	0.030 (5)	0.028 (5)	0.003 (4)	−0.005 (4)	−0.002 (4)
C15	0.039 (6)	0.036 (6)	0.036 (6)	−0.001 (5)	−0.010 (5)	0.000 (5)
C16	0.026 (5)	0.046 (6)	0.040 (6)	0.004 (5)	−0.007 (5)	−0.021 (5)
C17	0.036 (6)	0.043 (6)	0.034 (6)	0.010 (5)	−0.009 (5)	−0.004 (5)
C18	0.034 (6)	0.026 (5)	0.031 (6)	0.000 (4)	−0.001 (4)	0.000 (4)

O1—C1	1.340 (10)	C6—C11	1.402 (12)
O1—C12	1.433 (10)	C7—C8	1.388 (12)
O2—C1	1.218 (11)	C8—C9	1.381 (13)
O3—C3	1.433 (11)	C8—H8	0.9500
O3—H3O	0.84 (8)	C9—C10	1.384 (13)
O4—C4	1.205 (10)	C9—H9	0.9500
O5—N4	1.228 (10)	C10—C11	1.375 (12)
O6—N4	1.223 (10)	C10—H10	0.9500
N1—C1	1.369 (12)	C11—H11	0.9500
N1—C2	1.430 (11)	C12—C13	1.513 (13)
N1—H1N	0.88 (7)	C12—H12A	0.9900
N2—C4	1.358 (11)	C12—H12B	0.9900
N2—N3	1.383 (10)	C13—C14	1.379 (12)
N2—H2N	0.88 (4)	C13—C18	1.376 (13)
N3—C5	1.295 (11)	C14—C15	1.372 (13)
N4—C7	1.490 (11)	C14—H14	0.9500
C2—C4	1.544 (12)	C15—C16	1.376 (15)
C2—C3	1.541 (12)	C15—H15	0.9500
C2—H2	1.0000	C16—C17	1.381 (14)
C3—H3A	0.9900	C16—H16	0.9500
C3—H3B	0.9900	C17—C18	1.391 (13)
C5—C6	1.485 (12)	C17—H17	0.9500
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.387 (13)
C1—O1—C12	114.3 (7)	C8—C7—N4	115.2 (8)
C3—O3—H3O	110 (7)	C9—C8—C7	118.1 (8)
C1—N1—C2	119.6 (7)	C9—C8—H8	120.9
C1—N1—H1N	118 (6)	C7—C8—H8	120.9
C2—N1—H1N	116 (6)	C10—C9—C8	120.5 (8)
C4—N2—N3	116.5 (7)	C10—C9—H9	119.8
C4—N2—H2N	118 (6)	C8—C9—H9	119.8
N3—N2—H2N	123 (6)	C9—C10—C11	119.9 (9)
C5—N3—N2	115.3 (7)	C9—C10—H10	120.1
O6—N4—O5	123.4 (8)	C11—C10—H10	120.1
O6—N4—C7	119.1 (7)	C10—C11—C6	122.0 (8)
O5—N4—C7	117.5 (7)	C10—C11—H11	119.0
O2—C1—O1	124.3 (8)	C6—C11—H11	119.0
O2—C1—N1	124.7 (8)	O1—C12—C13	109.6 (7)
O1—C1—N1	111.0 (7)	O1—C12—H12A	109.7
N1—C2—C4	109.8 (7)	C13—C12—H12A	109.7
N1—C2—C3	109.1 (7)	O1—C12—H12B	109.7
C4—C2—C3	109.9 (7)	C13—C12—H12B	109.7
N1—C2—H2	109.3	H12A—C12—H12B	108.2
C4—C2—H2	109.3	C14—C13—C18	119.1 (8)
C3—C2—H2	109.3	C14—C13—C12	123.3 (8)
O3—C3—C2	112.7 (7)	C18—C13—C12	117.5 (8)
O3—C3—H3A	109.1	C13—C14—C15	120.9 (9)
C2—C3—H3A	109.1	C13—C14—H14	119.6
O3—C3—H3B	109.1	C15—C14—H14	119.6
C2—C3—H3B	109.1	C16—C15—C14	120.1 (10)
H3A—C3—H3B	107.8	C16—C15—H15	120.0
O4—C4—N2	124.3 (8)	C14—C15—H15	120.0
O4—C4—C2	121.9 (8)	C15—C16—C17	120.0 (9)
N2—C4—C2	113.7 (7)	C15—C16—H16	120.0
N3—C5—C6	114.6 (8)	C17—C16—H16	120.0
N3—C5—H5	122.7	C16—C17—C18	119.4 (10)
C6—C5—H5	122.7	C16—C17—H17	120.3
C7—C6—C11	115.8 (8)	C18—C17—H17	120.3
C7—C6—C5	127.2 (8)	C13—C18—C17	120.5 (9)
C11—C6—C5	117.0 (8)	C13—C18—H18	119.7
C6—C7—C8	123.6 (8)	C17—C18—H18	119.7
C6—C7—N4	121.2 (7)
C4—N2—N3—C5	−179.8 (9)	O6—N4—C7—C6	176.4 (9)
C12—O1—C1—O2	−5.2 (12)	O5—N4—C7—C6	−3.3 (12)
C12—O1—C1—N1	175.7 (7)	O6—N4—C7—C8	−2.2 (11)
C2—N1—C1—O2	−9.2 (13)	O5—N4—C7—C8	178.1 (8)
C2—N1—C1—O1	169.9 (7)	C6—C7—C8—C9	0.7 (13)
C1—N1—C2—C4	−76.5 (9)	N4—C7—C8—C9	179.2 (8)
C1—N1—C2—C3	163.0 (8)	C7—C8—C9—C10	−1.0 (14)
N1—C2—C3—O3	−73.3 (9)	C8—C9—C10—C11	1.9 (14)
C4—C2—C3—O3	166.2 (7)	C9—C10—C11—C6	−2.6 (14)
N3—N2—C4—O4	6.5 (13)	C7—C6—C11—C10	2.2 (12)
N3—N2—C4—C2	−176.0 (7)	C5—C6—C11—C10	−178.9 (8)
N1—C2—C4—O4	−20.2 (11)	C1—O1—C12—C13	−171.3 (8)
C3—C2—C4—O4	99.8 (10)	O1—C12—C13—C14	−2.3 (12)
N1—C2—C4—N2	162.3 (8)	O1—C12—C13—C18	177.0 (8)
C3—C2—C4—N2	−77.7 (9)	C18—C13—C14—C15	2.0 (14)
N2—N3—C5—C6	−174.3 (7)	C12—C13—C14—C15	−178.8 (9)
N3—C5—C6—C7	−137.9 (9)	C13—C14—C15—C16	−1.1 (15)
N3—C5—C6—C11	43.3 (12)	C14—C15—C16—C17	−0.2 (15)
C11—C6—C7—C8	−1.3 (12)	C15—C16—C17—C18	0.6 (15)
C5—C6—C7—C8	179.9 (9)	C14—C13—C18—C17	−1.6 (14)
C11—C6—C7—N4	−179.7 (8)	C12—C13—C18—C17	179.2 (9)
C5—C6—C7—N4	1.5 (13)	C16—C17—C18—C13	0.3 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2i	0.84 (8)	1.97 (9)	2.712 (9)	147 (8)
N1—H1n···O3ii	0.88 (7)	2.12 (7)	2.974 (10)	167 (8)
N2—H2n···O4iii	0.88 (4)	1.95 (5)	2.775 (10)	155 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O2i	0.84 (8)	1.97 (9)	2.712 (9)	147 (8)
N1—H1n⋯O3ii	0.88 (7)	2.12 (7)	2.974 (10)	167 (8)
N2—H2n⋯O4iii	0.88 (4)	1.95 (5)	2.775 (10)	155 (9)

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