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

The mol-ecule of the title compound, C(16)H(23)N(3)O(5), is twisted about the chiral C atom, the dihedral angle formed between the amide residues being 79.6 (3)°. The conformation about the imine bond [1.278 (5) Å] is E. In the crystal, O-H⋯O and N-H⋯O hydrogen bonding between the hy-droxy, amine and carbonyl groups leads 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 ▶, 2011 ▶); de Souza et al. (2010 ▶); Howie et al. (2011 ▶).

Experimental

Crystal data

C16H23N3O5

M = 337.38

Triclinic,

a = 5.3323 (4) Å

b = 5.7200 (4) Å

c = 14.3319 (10) Å

α = 79.919 (4)°

β = 83.686 (4)°

γ = 76.505 (4)°

V = 417.41 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 120 K

0.16 × 0.07 × 0.04 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

7495 measured reflections

1900 independent reflections

1661 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.113

S = 1.09

1900 reflections

230 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.25 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/S1600536811024263/hb5921sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024263/hb5921Isup2.hkl

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

C16H23N3O5	Z = 1
Mr = 337.38	F(000) = 180
Triclinic, P1	Dx = 1.342 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3323 (4) Å	Cell parameters from 14323 reflections
b = 5.7200 (4) Å	θ = 2.9–27.5°
c = 14.3319 (10) Å	µ = 0.10 mm−1
α = 79.919 (4)°	T = 120 K
β = 83.686 (4)°	Block, colourless
γ = 76.505 (4)°	0.16 × 0.07 × 0.04 mm
V = 417.41 (5) Å3

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	1900 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1661 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.7°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −7→7
Tmin = 0.887, Tmax = 1.000	l = −18→18
7495 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0304P)2 + 0.3732P] where P = (Fo2 + 2Fc2)/3
1900 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.24 e Å−3
6 restraints	Δρmin = −0.25 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	1.6917 (5)	0.8513 (5)	0.7563 (2)	0.0280 (7)
O2	0.9933 (5)	0.3081 (5)	0.3426 (2)	0.0259 (6)
O3	0.4988 (5)	0.1450 (5)	0.3533 (2)	0.0244 (6)
H3O	0.340 (3)	0.190 (9)	0.369 (3)	0.037*
O4	0.4967 (5)	0.9626 (5)	0.06608 (19)	0.0228 (6)
O5	0.2010 (5)	0.7831 (5)	0.1623 (2)	0.0250 (6)
N1	1.0286 (6)	0.6618 (6)	0.4406 (2)	0.0215 (7)
N2	0.8274 (6)	0.6827 (6)	0.3836 (2)	0.0209 (7)
H2N	0.709 (6)	0.818 (5)	0.373 (3)	0.025*
N3	0.6282 (6)	0.6919 (6)	0.1906 (2)	0.0212 (7)
H3N	0.777 (5)	0.731 (8)	0.171 (3)	0.025*
C1	1.2010 (7)	0.8412 (7)	0.5502 (3)	0.0194 (8)
C2	1.4019 (7)	0.6394 (7)	0.5725 (3)	0.0211 (8)
H2	1.4244	0.5028	0.5406	0.025*
C3	1.5699 (7)	0.6361 (7)	0.6412 (3)	0.0222 (8)
H3	1.7053	0.4975	0.6560	0.027*
C4	1.5392 (7)	0.8349 (7)	0.6876 (3)	0.0229 (8)
C5	1.3430 (8)	1.0405 (7)	0.6634 (3)	0.0256 (9)
H5	1.3242	1.1793	0.6937	0.031*
C6	1.1777 (8)	1.0429 (7)	0.5961 (3)	0.0251 (9)
H6	1.0453	1.1836	0.5805	0.030*
C7	1.8959 (8)	0.6473 (8)	0.7822 (3)	0.0280 (9)
H7A	1.8249	0.5017	0.8027	0.042*
H7B	1.9827	0.6773	0.8343	0.042*
H7C	2.0207	0.6225	0.7274	0.042*
C8	1.0108 (8)	0.8446 (7)	0.4829 (3)	0.0229 (8)
H8	0.8738	0.9833	0.4709	0.027*
C9	0.8245 (7)	0.4972 (7)	0.3388 (3)	0.0195 (7)
C10	0.5925 (7)	0.5327 (7)	0.2797 (3)	0.0188 (7)
H10	0.4336	0.6117	0.3161	0.023*
C11	0.5605 (7)	0.2847 (7)	0.2643 (3)	0.0226 (8)
H11A	0.4206	0.3063	0.2214	0.027*
H11B	0.7227	0.1972	0.2339	0.027*
C12	0.4209 (7)	0.8111 (7)	0.1416 (3)	0.0188 (7)
C13	0.3072 (7)	1.1111 (7)	−0.0009 (3)	0.0213 (8)
C14	0.4761 (8)	1.2529 (7)	−0.0707 (3)	0.0264 (9)
H14A	0.5607	1.3426	−0.0360	0.040*
H14B	0.3684	1.3678	−0.1172	0.040*
H14C	0.6079	1.1395	−0.1037	0.040*
C15	0.0964 (8)	1.2826 (7)	0.0503 (3)	0.0250 (8)
H15A	−0.0152	1.1886	0.0920	0.038*
H15B	−0.0070	1.4008	0.0034	0.038*
H15C	0.1759	1.3688	0.0882	0.038*
C16	0.1993 (8)	0.9468 (7)	−0.0514 (3)	0.0244 (8)
H16A	0.3423	0.8281	−0.0770	0.037*
H16B	0.0995	1.0457	−0.1036	0.037*
H16C	0.0868	0.8610	−0.0063	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.0280 (15)	0.0329 (16)	0.0243 (15)	−0.0048 (13)	−0.0056 (12)	−0.0074 (12)
O2	0.0193 (14)	0.0193 (13)	0.0391 (17)	−0.0037 (11)	−0.0067 (12)	−0.0026 (12)
O3	0.0160 (13)	0.0238 (14)	0.0286 (15)	−0.0031 (11)	−0.0011 (11)	0.0066 (11)
O4	0.0181 (13)	0.0237 (14)	0.0246 (14)	−0.0042 (11)	−0.0059 (11)	0.0041 (11)
O5	0.0229 (15)	0.0279 (15)	0.0241 (15)	−0.0076 (12)	−0.0041 (11)	0.0006 (12)
N1	0.0212 (16)	0.0245 (16)	0.0186 (16)	−0.0052 (13)	−0.0055 (12)	−0.0005 (13)
N2	0.0183 (16)	0.0231 (17)	0.0203 (17)	−0.0016 (13)	−0.0073 (13)	−0.0007 (13)
N3	0.0152 (15)	0.0221 (17)	0.0242 (17)	−0.0044 (12)	−0.0026 (13)	0.0034 (13)
C1	0.0201 (18)	0.0232 (19)	0.0155 (18)	−0.0087 (15)	−0.0010 (14)	0.0007 (14)
C2	0.0208 (19)	0.0228 (19)	0.0201 (19)	−0.0046 (16)	0.0018 (15)	−0.0072 (15)
C3	0.0189 (19)	0.026 (2)	0.0206 (19)	−0.0025 (15)	−0.0029 (15)	−0.0012 (16)
C4	0.0205 (19)	0.027 (2)	0.022 (2)	−0.0094 (16)	0.0011 (16)	0.0001 (16)
C5	0.028 (2)	0.0212 (19)	0.027 (2)	−0.0024 (16)	−0.0023 (17)	−0.0058 (16)
C6	0.026 (2)	0.0185 (18)	0.029 (2)	0.0007 (15)	−0.0069 (17)	−0.0021 (15)
C7	0.025 (2)	0.035 (2)	0.023 (2)	−0.0076 (18)	−0.0057 (16)	0.0015 (17)
C8	0.0228 (19)	0.0221 (19)	0.022 (2)	−0.0055 (15)	−0.0005 (15)	0.0016 (15)
C9	0.0176 (18)	0.0182 (17)	0.0209 (19)	−0.0059 (14)	0.0027 (14)	0.0020 (14)
C10	0.0157 (17)	0.0221 (18)	0.0180 (18)	−0.0044 (14)	−0.0016 (14)	−0.0008 (14)
C11	0.023 (2)	0.0199 (19)	0.025 (2)	−0.0073 (15)	−0.0042 (16)	0.0023 (15)
C12	0.0202 (19)	0.0202 (18)	0.0161 (18)	−0.0072 (14)	−0.0012 (14)	0.0001 (14)
C13	0.0178 (18)	0.0227 (19)	0.0209 (19)	−0.0029 (15)	−0.0051 (15)	0.0042 (15)
C14	0.027 (2)	0.022 (2)	0.027 (2)	−0.0028 (16)	−0.0056 (17)	0.0027 (16)
C15	0.027 (2)	0.022 (2)	0.024 (2)	−0.0027 (16)	−0.0046 (16)	−0.0024 (15)
C16	0.026 (2)	0.0255 (19)	0.022 (2)	−0.0068 (16)	−0.0025 (16)	−0.0036 (16)

O1—C4	1.372 (5)	C5—H5	0.9500
O1—C7	1.425 (5)	C6—H6	0.9500
O2—C9	1.233 (5)	C7—H7A	0.9800
O3—C11	1.431 (4)	C7—H7B	0.9800
O3—H3O	0.841 (10)	C7—H7C	0.9800
O4—C12	1.350 (4)	C8—H8	0.9500
O4—C13	1.480 (4)	C9—C10	1.530 (5)
O5—C12	1.218 (4)	C10—C11	1.524 (5)
N1—C8	1.278 (5)	C10—H10	1.0000
N1—N2	1.389 (4)	C11—H11A	0.9900
N2—C9	1.336 (5)	C11—H11B	0.9900
N2—H2N	0.880 (10)	C13—C15	1.523 (5)
N3—C12	1.353 (5)	C13—C16	1.523 (5)
N3—C10	1.455 (5)	C13—C14	1.526 (5)
N3—H3N	0.880 (10)	C14—H14A	0.9800
C1—C2	1.397 (5)	C14—H14B	0.9800
C1—C6	1.401 (6)	C14—H14C	0.9800
C1—C8	1.469 (5)	C15—H15A	0.9800
C2—C3	1.397 (5)	C15—H15B	0.9800
C2—H2	0.9500	C15—H15C	0.9800
C3—C4	1.385 (5)	C16—H16A	0.9800
C3—H3	0.9500	C16—H16B	0.9800
C4—C5	1.400 (6)	C16—H16C	0.9800
C5—C6	1.372 (6)
C4—O1—C7	117.4 (3)	N3—C10—C11	112.2 (3)
C11—O3—H3O	109 (3)	N3—C10—C9	109.8 (3)
C12—O4—C13	120.5 (3)	C11—C10—C9	109.1 (3)
C8—N1—N2	114.4 (3)	N3—C10—H10	108.6
C9—N2—N1	118.8 (3)	C11—C10—H10	108.6
C9—N2—H2N	119 (3)	C9—C10—H10	108.6
N1—N2—H2N	122 (3)	O3—C11—C10	110.0 (3)
C12—N3—C10	119.8 (3)	O3—C11—H11A	109.7
C12—N3—H3N	117 (3)	C10—C11—H11A	109.7
C10—N3—H3N	122 (3)	O3—C11—H11B	109.7
C2—C1—C6	118.3 (4)	C10—C11—H11B	109.7
C2—C1—C8	122.2 (3)	H11A—C11—H11B	108.2
C6—C1—C8	119.5 (3)	O5—C12—N3	124.9 (3)
C1—C2—C3	120.8 (3)	O5—C12—O4	125.6 (3)
C1—C2—H2	119.6	N3—C12—O4	109.5 (3)
C3—C2—H2	119.6	O4—C13—C15	110.6 (3)
C4—C3—C2	120.0 (3)	O4—C13—C16	110.2 (3)
C4—C3—H3	120.0	C15—C13—C16	112.6 (3)
C2—C3—H3	120.0	O4—C13—C14	101.7 (3)
O1—C4—C3	125.0 (3)	C15—C13—C14	110.9 (3)
O1—C4—C5	115.6 (3)	C16—C13—C14	110.4 (3)
C3—C4—C5	119.4 (3)	C13—C14—H14A	109.5
C6—C5—C4	120.4 (4)	C13—C14—H14B	109.5
C6—C5—H5	119.8	H14A—C14—H14B	109.5
C4—C5—H5	119.8	C13—C14—H14C	109.5
C5—C6—C1	121.0 (4)	H14A—C14—H14C	109.5
C5—C6—H6	119.5	H14B—C14—H14C	109.5
C1—C6—H6	119.5	C13—C15—H15A	109.5
O1—C7—H7A	109.5	C13—C15—H15B	109.5
O1—C7—H7B	109.5	H15A—C15—H15B	109.5
H7A—C7—H7B	109.5	C13—C15—H15C	109.5
O1—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	120.4 (3)	C13—C16—H16B	109.5
N1—C8—H8	119.8	H16A—C16—H16B	109.5
C1—C8—H8	119.8	C13—C16—H16C	109.5
O2—C9—N2	124.3 (4)	H16A—C16—H16C	109.5
O2—C9—C10	120.3 (3)	H16B—C16—H16C	109.5
N2—C9—C10	115.4 (3)
C8—N1—N2—C9	−177.8 (3)	N1—N2—C9—C10	178.5 (3)
C6—C1—C2—C3	2.0 (6)	C12—N3—C10—C11	79.8 (4)
C8—C1—C2—C3	−176.0 (4)	C12—N3—C10—C9	−158.7 (3)
C1—C2—C3—C4	−0.3 (6)	O2—C9—C10—N3	−102.2 (4)
C7—O1—C4—C3	−0.5 (5)	N2—C9—C10—N3	77.5 (4)
C7—O1—C4—C5	−179.2 (4)	O2—C9—C10—C11	21.1 (5)
C2—C3—C4—O1	179.7 (4)	N2—C9—C10—C11	−159.2 (3)
C2—C3—C4—C5	−1.6 (6)	N3—C10—C11—O3	−173.9 (3)
O1—C4—C5—C6	−179.4 (4)	C9—C10—C11—O3	64.3 (4)
C3—C4—C5—C6	1.8 (6)	C10—N3—C12—O5	−5.9 (6)
C4—C5—C6—C1	−0.1 (6)	C10—N3—C12—O4	174.9 (3)
C2—C1—C6—C5	−1.8 (6)	C13—O4—C12—O5	−0.7 (5)
C8—C1—C6—C5	176.2 (4)	C13—O4—C12—N3	178.6 (3)
N2—N1—C8—C1	176.1 (3)	C12—O4—C13—C15	60.9 (4)
C2—C1—C8—N1	−1.8 (5)	C12—O4—C13—C16	−64.3 (4)
C6—C1—C8—N1	−179.8 (4)	C12—O4—C13—C14	178.7 (3)
N1—N2—C9—O2	−1.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2i	0.84 (3)	1.87 (3)	2.651 (4)	153 (4)
N2—H2n···O3ii	0.88 (3)	1.93 (3)	2.803 (4)	169 (3)
N3—H3n···O5iii	0.88 (3)	2.34 (3)	3.188 (4)	164 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O2i	0.84 (3)	1.87 (3)	2.651 (4)	153 (4)
N2—H2n⋯O3ii	0.88 (3)	1.93 (3)	2.803 (4)	169 (3)
N3—H3n⋯O5iii	0.88 (3)	2.34 (3)	3.188 (4)	164 (4)

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