tert-Butyl N-((1S)-2-hy-droxy-1-{N'-[(E)-2-hy-droxy-4-meth-oxy-benzyl-idene]hydrazinecarbon-yl}eth-yl)carbamate.

The mol-ecule of the title compound, C(16)H(23)N(3)O(6), is twisted about the chiral C atom with the dihedral angle formed between the amide residues being 76.9 (3)°. Overall, the mol-ecule is curved with the terminal organic groups lying to the same side. The conformation about the imine bond [1.291 (5) Å] is E and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds involving the hy-droxy, amine and carbonyl groups lead to the formation of supra-molecular layers, which stack along the c-axis direction.

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 ▶); Tiekink et al. (2011 ▶).

Experimental

Crystal data

C16H23N3O6

M = 353.37

Triclinic,

a = 5.3101 (14) Å

b = 5.7301 (13) Å

c = 14.651 (4) Å

α = 80.364 (16)°

β = 84.788 (11)°

γ = 74.845 (15)°

V = 423.70 (19) Å3

Z = 1

Mo Kα radiation

μ = 0.11 mm−1

T = 120 K

0.62 × 0.18 × 0.03 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.415, T max = 0.746

7849 measured reflections

1936 independent reflections

1639 reflections with I > 2σ(I)

R int = 0.092

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.158

S = 1.06

1936 reflections

242 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 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 datablock(s) global, I. DOI: 10.1107/S1600536811025293/hb5936sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025293/hb5936Isup2.hkl

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

C16H23N3O6	Z = 1
Mr = 353.37	F(000) = 188
Triclinic, P1	Dx = 1.385 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3101 (14) Å	Cell parameters from 41272 reflections
b = 5.7301 (13) Å	θ = 2.9–27.5°
c = 14.651 (4) Å	µ = 0.11 mm−1
α = 80.364 (16)°	T = 120 K
β = 84.788 (11)°	Lath, colourless
γ = 74.845 (15)°	0.62 × 0.18 × 0.03 mm
V = 423.70 (19) Å3

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	1936 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1639 reflections with I > 2σ(I)
graphite	Rint = 0.092
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 = −7→7
Tmin = 0.415, Tmax = 0.746	l = −18→18
7849 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)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.0932P)2 + 0.0716P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1936 reflections	Δρmax = 0.26 e Å−3
242 parameters	Δρmin = −0.32 e Å−3
7 restraints	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	1.3235 (6)	−0.0932 (5)	1.0670 (2)	0.0337 (7)
H1o	1.233 (10)	−0.078 (11)	1.021 (3)	0.051*
O2	1.5080 (6)	0.3094 (6)	1.3026 (2)	0.0365 (7)
O3	0.8525 (6)	−0.2427 (5)	0.8860 (2)	0.0359 (7)
O4	0.3605 (6)	−0.3907 (5)	0.8847 (2)	0.0330 (7)
H4o	0.201 (3)	−0.351 (11)	0.901 (4)	0.049*
O5	0.0570 (6)	0.2513 (5)	0.7006 (2)	0.0318 (7)
O6	0.3497 (6)	0.4260 (5)	0.6066 (2)	0.0307 (7)
N1	0.8884 (7)	0.1219 (6)	0.9773 (2)	0.0296 (8)
N2	0.6946 (7)	0.1467 (6)	0.9162 (2)	0.0289 (7)
H2n	0.564 (7)	0.277 (6)	0.907 (3)	0.035*
N3	0.4886 (7)	0.1547 (6)	0.7304 (2)	0.0290 (8)
H3n	0.630 (6)	0.207 (9)	0.712 (3)	0.035*
C1	1.0379 (8)	0.2948 (7)	1.0923 (3)	0.0277 (8)
C2	1.2576 (8)	0.1000 (7)	1.1135 (3)	0.0296 (9)
C3	1.4175 (8)	0.0995 (7)	1.1835 (3)	0.0285 (8)
H3	1.5648	−0.0341	1.1972	0.034*
C4	1.3625 (8)	0.2931 (8)	1.2332 (3)	0.0311 (9)
C5	1.1485 (10)	0.4908 (8)	1.2127 (3)	0.0360 (10)
H5	1.1141	0.6261	1.2456	0.043*
C6	0.9868 (9)	0.4896 (8)	1.1443 (3)	0.0351 (10)
H6	0.8381	0.6226	1.1320	0.042*
C7	1.7297 (9)	0.1110 (9)	1.3266 (3)	0.0380 (10)
H7A	1.6729	−0.0403	1.3454	0.057*
H7B	1.8147	0.1440	1.3779	0.057*
H7C	1.8534	0.0933	1.2728	0.057*
C8	0.8536 (9)	0.2999 (8)	1.0244 (3)	0.0313 (9)
H8	0.7059	0.4353	1.0146	0.038*
C9	0.6886 (8)	−0.0437 (7)	0.8759 (3)	0.0298 (9)
C10	0.4544 (8)	−0.0039 (7)	0.8164 (3)	0.0283 (9)
H10	0.2931	0.0778	0.8509	0.034*
C11	0.4262 (9)	−0.2510 (7)	0.7997 (3)	0.0322 (9)
H11A	0.2880	−0.2258	0.7554	0.039*
H11B	0.5923	−0.3421	0.7720	0.039*
C12	0.2788 (8)	0.2769 (7)	0.6807 (3)	0.0279 (8)
C13	0.1569 (8)	0.5755 (7)	0.5405 (3)	0.0296 (9)
C14	−0.0560 (9)	0.7519 (8)	0.5888 (3)	0.0353 (10)
H14A	−0.1694	0.6616	0.6280	0.053*
H14B	−0.1596	0.8736	0.5424	0.053*
H14C	0.0236	0.8347	0.6274	0.053*
C15	0.3213 (9)	0.7096 (8)	0.4718 (3)	0.0347 (10)
H15A	0.4001	0.8072	0.5042	0.052*
H15B	0.2106	0.8176	0.4239	0.052*
H15C	0.4595	0.5908	0.4428	0.052*
C16	0.0458 (9)	0.4084 (8)	0.4931 (3)	0.0337 (9)
H16A	0.1896	0.2843	0.4694	0.051*
H16B	−0.0583	0.5058	0.4416	0.051*
H16C	−0.0651	0.3282	0.5380	0.051*

	U11	U22	U33	U12	U13	U23
O1	0.0317 (16)	0.0303 (15)	0.0357 (16)	0.0037 (12)	−0.0057 (12)	−0.0114 (12)
O2	0.0309 (17)	0.0413 (18)	0.0365 (17)	−0.0023 (13)	−0.0052 (13)	−0.0125 (13)
O3	0.0266 (16)	0.0257 (15)	0.0500 (19)	0.0022 (12)	−0.0051 (13)	−0.0032 (13)
O4	0.0271 (15)	0.0236 (14)	0.0406 (17)	0.0028 (12)	−0.0029 (13)	0.0025 (12)
O5	0.0281 (16)	0.0255 (15)	0.0386 (17)	−0.0033 (11)	−0.0039 (12)	−0.0002 (12)
O6	0.0267 (15)	0.0273 (14)	0.0327 (15)	0.0000 (11)	−0.0064 (12)	0.0023 (11)
N1	0.0277 (18)	0.0285 (18)	0.0288 (17)	−0.0005 (14)	−0.0054 (13)	−0.0018 (14)
N2	0.0253 (18)	0.0279 (18)	0.0296 (17)	0.0007 (13)	−0.0051 (14)	−0.0027 (14)
N3	0.0272 (18)	0.0242 (17)	0.0315 (18)	−0.0005 (14)	−0.0037 (14)	−0.0007 (14)
C1	0.028 (2)	0.025 (2)	0.028 (2)	−0.0023 (16)	−0.0034 (15)	−0.0022 (15)
C2	0.030 (2)	0.025 (2)	0.031 (2)	−0.0014 (17)	0.0016 (17)	−0.0060 (16)
C3	0.026 (2)	0.0257 (19)	0.031 (2)	0.0015 (15)	−0.0026 (16)	−0.0059 (15)
C4	0.031 (2)	0.032 (2)	0.028 (2)	−0.0038 (17)	0.0016 (17)	−0.0050 (17)
C5	0.045 (3)	0.029 (2)	0.033 (2)	−0.0061 (19)	−0.0011 (19)	−0.0093 (17)
C6	0.035 (2)	0.025 (2)	0.038 (2)	0.0014 (17)	−0.0014 (18)	−0.0016 (17)
C7	0.039 (3)	0.036 (2)	0.035 (2)	−0.002 (2)	−0.0066 (19)	−0.0059 (19)
C8	0.031 (2)	0.027 (2)	0.033 (2)	−0.0033 (17)	−0.0044 (17)	−0.0004 (16)
C9	0.028 (2)	0.0241 (19)	0.031 (2)	0.0029 (16)	−0.0033 (16)	−0.0017 (15)
C10	0.027 (2)	0.0256 (19)	0.028 (2)	0.0012 (16)	−0.0030 (16)	−0.0021 (15)
C11	0.034 (2)	0.027 (2)	0.032 (2)	0.0005 (17)	−0.0032 (18)	−0.0045 (17)
C12	0.030 (2)	0.0211 (18)	0.029 (2)	0.0001 (15)	−0.0033 (16)	−0.0017 (15)
C13	0.031 (2)	0.0217 (19)	0.031 (2)	0.0020 (16)	−0.0042 (16)	−0.0005 (15)
C14	0.039 (2)	0.026 (2)	0.035 (2)	0.0025 (18)	−0.0022 (18)	−0.0044 (17)
C15	0.036 (2)	0.028 (2)	0.035 (2)	0.0008 (18)	−0.0037 (18)	−0.0020 (17)
C16	0.034 (2)	0.028 (2)	0.037 (2)	−0.0026 (17)	−0.0051 (18)	−0.0062 (17)

O1—C2	1.348 (5)	C5—C6	1.379 (7)
O1—H1o	0.842 (11)	C5—H5	0.9500
O2—C4	1.362 (5)	C6—H6	0.9500
O2—C7	1.429 (5)	C7—H7A	0.9800
O3—C9	1.236 (5)	C7—H7B	0.9800
O4—C11	1.432 (5)	C7—H7C	0.9800
O4—H4o	0.841 (11)	C8—H8	0.9500
O5—C12	1.228 (5)	C9—C10	1.530 (6)
O6—C12	1.353 (5)	C10—C11	1.523 (6)
O6—C13	1.472 (5)	C10—H10	1.0000
N1—C8	1.291 (5)	C11—H11A	0.9900
N1—N2	1.388 (5)	C11—H11B	0.9900
N2—C9	1.333 (5)	C13—C14	1.516 (6)
N2—H2n	0.880 (10)	C13—C15	1.516 (6)
N3—C12	1.353 (5)	C13—C16	1.529 (6)
N3—C10	1.452 (5)	C14—H14A	0.9800
N3—H3n	0.882 (11)	C14—H14B	0.9800
C1—C2	1.404 (5)	C14—H14C	0.9800
C1—C6	1.410 (6)	C15—H15A	0.9800
C1—C8	1.449 (6)	C15—H15B	0.9800
C2—C3	1.389 (6)	C15—H15C	0.9800
C3—C4	1.381 (6)	C16—H16A	0.9800
C3—H3	0.9500	C16—H16B	0.9800
C4—C5	1.393 (6)	C16—H16C	0.9800
C2—O1—H1o	114 (4)	N2—C9—C10	115.1 (3)
C4—O2—C7	117.7 (3)	N3—C10—C11	112.1 (3)
C11—O4—H4o	114 (4)	N3—C10—C9	109.5 (3)
C12—O6—C13	121.0 (3)	C11—C10—C9	109.2 (3)
C8—N1—N2	114.7 (3)	N3—C10—H10	108.6
C9—N2—N1	119.3 (3)	C11—C10—H10	108.6
C9—N2—H2n	117 (3)	C9—C10—H10	108.6
N1—N2—H2n	124 (3)	O4—C11—C10	110.7 (3)
C12—N3—C10	119.8 (3)	O4—C11—H11A	109.5
C12—N3—H3n	113 (3)	C10—C11—H11A	109.5
C10—N3—H3n	126 (3)	O4—C11—H11B	109.5
C2—C1—C6	117.6 (4)	C10—C11—H11B	109.5
C2—C1—C8	123.9 (4)	H11A—C11—H11B	108.1
C6—C1—C8	118.4 (4)	O5—C12—N3	123.8 (4)
O1—C2—C3	117.1 (3)	O5—C12—O6	125.6 (4)
O1—C2—C1	121.9 (4)	N3—C12—O6	110.5 (4)
C3—C2—C1	121.0 (4)	O6—C13—C14	110.6 (3)
C4—C3—C2	120.1 (4)	O6—C13—C15	102.4 (3)
C4—C3—H3	120.0	C14—C13—C15	111.4 (3)
C2—C3—H3	120.0	O6—C13—C16	109.5 (3)
O2—C4—C3	124.3 (4)	C14—C13—C16	111.9 (4)
O2—C4—C5	115.4 (4)	C15—C13—C16	110.7 (4)
C3—C4—C5	120.2 (4)	C13—C14—H14A	109.5
C6—C5—C4	119.8 (4)	C13—C14—H14B	109.5
C6—C5—H5	120.1	H14A—C14—H14B	109.5
C4—C5—H5	120.1	C13—C14—H14C	109.5
C5—C6—C1	121.3 (4)	H14A—C14—H14C	109.5
C5—C6—H6	119.3	H14B—C14—H14C	109.5
C1—C6—H6	119.3	C13—C15—H15A	109.5
O2—C7—H7A	109.5	C13—C15—H15B	109.5
O2—C7—H7B	109.5	H15A—C15—H15B	109.5
H7A—C7—H7B	109.5	C13—C15—H15C	109.5
O2—C7—H7C	109.5	H15A—C15—H15C	109.5
H7A—C7—H7C	109.5	H15B—C15—H15C	109.5
H7B—C7—H7C	109.5	C13—C16—H16A	109.5
N1—C8—C1	120.5 (4)	C13—C16—H16B	109.5
N1—C8—H8	119.7	H16A—C16—H16B	109.5
C1—C8—H8	119.7	C13—C16—H16C	109.5
O3—C9—N2	124.3 (4)	H16A—C16—H16C	109.5
O3—C9—C10	120.6 (4)	H16B—C16—H16C	109.5
C8—N1—N2—C9	−168.9 (4)	C6—C1—C8—N1	−177.9 (4)
C6—C1—C2—O1	−179.4 (4)	N1—N2—C9—O3	−3.1 (6)
C8—C1—C2—O1	4.4 (6)	N1—N2—C9—C10	175.1 (3)
C6—C1—C2—C3	0.3 (6)	C12—N3—C10—C11	79.4 (4)
C8—C1—C2—C3	−175.8 (4)	C12—N3—C10—C9	−159.2 (3)
O1—C2—C3—C4	179.4 (4)	O3—C9—C10—N3	−107.6 (4)
C1—C2—C3—C4	−0.4 (6)	N2—C9—C10—N3	74.1 (4)
C7—O2—C4—C3	−1.1 (6)	O3—C9—C10—C11	15.5 (5)
C7—O2—C4—C5	179.9 (4)	N2—C9—C10—C11	−162.8 (4)
C2—C3—C4—O2	−179.7 (4)	N3—C10—C11—O4	−172.8 (3)
C2—C3—C4—C5	−0.8 (6)	C9—C10—C11—O4	65.6 (4)
O2—C4—C5—C6	−179.0 (4)	C10—N3—C12—O5	−4.8 (6)
C3—C4—C5—C6	1.9 (7)	C10—N3—C12—O6	176.0 (3)
C4—C5—C6—C1	−2.0 (7)	C13—O6—C12—O5	−0.4 (6)
C2—C1—C6—C5	0.9 (7)	C13—O6—C12—N3	178.8 (3)
C8—C1—C6—C5	177.2 (4)	C12—O6—C13—C14	60.8 (5)
N2—N1—C8—C1	178.5 (4)	C12—O6—C13—C15	179.6 (3)
C2—C1—C8—N1	−1.8 (7)	C12—O6—C13—C16	−62.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.84 (5)	1.99 (6)	2.666 (5)	137 (5)
O4—H4o···O3i	0.84 (3)	1.81 (3)	2.607 (5)	157 (6)
N2—H2n···O4ii	0.88 (4)	1.92 (3)	2.769 (5)	163 (4)
N3—H3n···O5iii	0.88 (4)	2.34 (4)	3.188 (5)	162 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.84 (5)	1.99 (6)	2.666 (5)	137 (5)
O4—H4o⋯O3i	0.84 (3)	1.81 (3)	2.607 (5)	157 (6)
N2—H2n⋯O4ii	0.88 (4)	1.92 (3)	2.769 (5)	163 (4)
N3—H3n⋯O5iii	0.88 (4)	2.34 (4)	3.188 (5)	162 (4)

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