Benzyl N-[(S)-2-hy-droxy-1-({[(E)-2-hy-droxy-4-meth-oxy-benzyl-idene]hydrazin-yl}carbon-yl)eth-yl]carbamate.

The shape of the title compound, C(19)H(21)N(3)O(6), is curved with the conformation about the imine bond [1.291 (3) Å] being E. While the hy-droxy-substituted benzene ring is almost coplanar with the hydrazinyl residue [N-N-C-C = 177.31 (18)°], an observation correlated with an intra-molecular O-H⋯N hydrogen bond leading to an S(6) ring, the remaining residues exhibit significant twists. The carbonyl residues are directed away from each other as are the amines. This allows for the formation of O-H⋯O and N-H⋯O hydrogen bonds in the crystal, which lead to two-dimensional supra-molecular arrays in the ac plane. Additional stabilization to the layers is afforded by C-H⋯π inter-actions.

Related literature

For the use of l-serine derivatives in anti-tumour therapy, see: Jiao et al. (2009 ▶); Yakura et al. (2007 ▶); Takahashi et al. (1988 ▶); Sin et al. (1998 ▶). For the use of N-acyl­hydrazones derivatives from l-serine in anti-tumour testing, see: Rollas & Küçükgüzel (2007 ▶); Terzioğlu & Gürsoy (2003 ▶). For a related structure, see: Pinheiro et al. (2010 ▶).

Experimental

Crystal data

C19H21N3O6

M = 387.39

Monoclinic,

a = 5.1634 (2) Å

b = 32.3173 (11) Å

c = 5.7030 (2) Å

β = 103.918 (2)°

V = 923.70 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 120 K

0.50 × 0.32 × 0.10 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.623, T max = 0.746

9676 measured reflections

2151 independent reflections

1954 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.078

S = 1.01

2149 reflections

266 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.19 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/S1600536810047720/hb5744sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047720/hb5744Isup2.hkl

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

C19H21N3O6	F(000) = 408
Mr = 387.39	Dx = 1.393 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9310 reflections
a = 5.1634 (2) Å	θ = 2.9–27.5°
b = 32.3173 (11) Å	µ = 0.11 mm−1
c = 5.7030 (2) Å	T = 120 K
β = 103.918 (2)°	Prism, colourless
V = 923.70 (6) Å3	0.50 × 0.32 × 0.10 mm
Z = 2

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	2151 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1954 reflections with I > 2σ(I)
graphite	Rint = 0.035
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 = −41→41
Tmin = 0.623, Tmax = 0.746	l = −7→7
9676 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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.1213P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2149 reflections	Δρmax = 0.14 e Å−3
266 parameters	Δρmin = −0.19 e Å−3
5 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	−0.1786 (3)	1.07693 (5)	0.1104 (3)	0.0267 (3)
H1O	−0.050 (4)	1.0606 (8)	0.111 (5)	0.040*
O2	−0.3856 (3)	1.18463 (5)	0.6089 (3)	0.0345 (4)
O3	0.3291 (3)	0.99440 (5)	−0.1161 (3)	0.0296 (4)
O4	0.8158 (3)	0.98932 (5)	−0.2785 (3)	0.0292 (3)
H4O	0.981 (2)	0.9933 (11)	−0.240 (5)	0.044*
O5	1.1738 (3)	0.91538 (5)	0.3209 (3)	0.0280 (3)
O6	0.9066 (3)	0.87370 (4)	0.4806 (3)	0.0232 (3)
N1	0.2721 (4)	1.03527 (5)	0.2864 (3)	0.0229 (4)
N2	0.4763 (3)	1.00743 (5)	0.2848 (3)	0.0225 (4)
H2N	0.597 (4)	1.0034 (8)	0.415 (3)	0.027*
N3	0.7233 (3)	0.92467 (5)	0.2328 (3)	0.0214 (4)
H3N	0.575 (3)	0.9171 (8)	0.263 (4)	0.026*
C1	0.1100 (4)	1.08823 (6)	0.5067 (4)	0.0234 (4)
C2	−0.1163 (4)	1.09787 (7)	0.3212 (4)	0.0225 (4)
C3	−0.2859 (4)	1.13016 (7)	0.3504 (4)	0.0251 (4)
H3	−0.4368	1.1368	0.2240	0.030*
C4	−0.2330 (5)	1.15243 (6)	0.5648 (4)	0.0267 (5)
C5	−0.0123 (5)	1.14263 (8)	0.7516 (4)	0.0310 (5)
H5	0.0222	1.1578	0.8987	0.037*
C6	0.1537 (5)	1.11119 (7)	0.7217 (4)	0.0291 (5)
H6	0.3029	1.1047	0.8500	0.035*
C7	−0.6104 (5)	1.19656 (7)	0.4213 (5)	0.0332 (5)
H7A	−0.5516	1.2027	0.2740	0.050*
H7B	−0.6934	1.2212	0.4717	0.050*
H7C	−0.7403	1.1739	0.3896	0.050*
C8	0.3021 (4)	1.05654 (7)	0.4826 (4)	0.0243 (4)
H8	0.4518	1.0514	0.6132	0.029*
C9	0.4915 (4)	0.98936 (6)	0.0787 (4)	0.0205 (4)
C10	0.7381 (4)	0.96234 (6)	0.0944 (4)	0.0194 (4)
H10	0.8987	0.9784	0.1799	0.023*
C11	0.7671 (4)	0.95243 (7)	−0.1585 (4)	0.0243 (4)
H11A	0.9168	0.9329	−0.1487	0.029*
H11B	0.6019	0.9390	−0.2521	0.029*
C12	0.9530 (4)	0.90556 (6)	0.3433 (4)	0.0215 (4)
C13	1.1447 (4)	0.85176 (7)	0.6038 (4)	0.0309 (5)
H13A	1.2736	0.8713	0.7031	0.037*
H13B	1.2301	0.8387	0.4844	0.037*
C14	1.0676 (4)	0.81910 (7)	0.7625 (4)	0.0269 (5)
C15	1.1859 (5)	0.78017 (7)	0.7770 (5)	0.0355 (6)
H15	1.3004	0.7736	0.6746	0.043*
C16	1.1382 (5)	0.75094 (8)	0.9394 (5)	0.0394 (6)
H16	1.2225	0.7247	0.9493	0.047*
C17	0.9694 (5)	0.75974 (8)	1.0862 (4)	0.0347 (5)
H17	0.9395	0.7398	1.1991	0.042*
C18	0.8429 (5)	0.79800 (8)	1.0684 (4)	0.0358 (6)
H18	0.7217	0.8039	1.1656	0.043*
C19	0.8938 (5)	0.82745 (7)	0.9084 (4)	0.0315 (5)
H19	0.8087	0.8537	0.8984	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0242 (8)	0.0238 (8)	0.0305 (8)	0.0034 (6)	0.0034 (6)	−0.0037 (6)
O2	0.0306 (9)	0.0285 (8)	0.0460 (10)	0.0027 (7)	0.0122 (7)	−0.0117 (7)
O3	0.0182 (7)	0.0414 (9)	0.0264 (8)	0.0038 (7)	−0.0003 (6)	0.0081 (7)
O4	0.0185 (7)	0.0398 (9)	0.0280 (7)	−0.0006 (7)	0.0031 (6)	0.0156 (7)
O5	0.0189 (7)	0.0290 (8)	0.0369 (8)	0.0027 (6)	0.0084 (6)	0.0102 (7)
O6	0.0179 (7)	0.0238 (7)	0.0278 (8)	0.0034 (6)	0.0052 (6)	0.0083 (6)
N1	0.0204 (9)	0.0178 (9)	0.0309 (9)	0.0042 (7)	0.0070 (7)	0.0049 (7)
N2	0.0186 (8)	0.0203 (8)	0.0268 (9)	0.0048 (7)	0.0022 (7)	0.0048 (7)
N3	0.0163 (8)	0.0220 (9)	0.0263 (9)	0.0011 (6)	0.0062 (7)	0.0071 (7)
C1	0.0250 (11)	0.0201 (10)	0.0265 (11)	−0.0013 (8)	0.0088 (8)	0.0037 (8)
C2	0.0219 (10)	0.0199 (10)	0.0278 (11)	−0.0037 (8)	0.0098 (8)	0.0005 (8)
C3	0.0196 (10)	0.0229 (10)	0.0332 (11)	−0.0014 (8)	0.0071 (8)	−0.0020 (9)
C4	0.0281 (11)	0.0193 (10)	0.0368 (13)	−0.0021 (8)	0.0162 (9)	−0.0020 (9)
C5	0.0379 (13)	0.0275 (12)	0.0288 (11)	−0.0028 (10)	0.0102 (10)	−0.0021 (9)
C6	0.0336 (12)	0.0276 (11)	0.0248 (11)	0.0013 (10)	0.0043 (9)	0.0028 (9)
C7	0.0298 (12)	0.0246 (11)	0.0480 (14)	0.0019 (9)	0.0147 (10)	−0.0025 (11)
C8	0.0245 (10)	0.0204 (10)	0.0283 (11)	0.0000 (8)	0.0069 (8)	0.0054 (9)
C9	0.0165 (9)	0.0198 (10)	0.0244 (10)	−0.0010 (8)	0.0036 (7)	0.0049 (8)
C10	0.0154 (9)	0.0210 (10)	0.0207 (9)	−0.0016 (8)	0.0020 (7)	0.0046 (8)
C11	0.0245 (11)	0.0261 (11)	0.0225 (10)	0.0002 (8)	0.0059 (8)	0.0040 (9)
C12	0.0213 (10)	0.0213 (10)	0.0224 (9)	0.0024 (8)	0.0065 (8)	0.0027 (8)
C13	0.0222 (11)	0.0295 (12)	0.0396 (13)	0.0071 (9)	0.0047 (9)	0.0159 (11)
C14	0.0243 (11)	0.0252 (11)	0.0286 (11)	−0.0002 (8)	0.0010 (9)	0.0058 (9)
C15	0.0369 (14)	0.0303 (12)	0.0428 (14)	0.0085 (10)	0.0166 (11)	0.0103 (11)
C16	0.0460 (15)	0.0262 (12)	0.0500 (15)	0.0085 (11)	0.0192 (12)	0.0128 (11)
C17	0.0452 (15)	0.0279 (12)	0.0314 (12)	−0.0017 (10)	0.0099 (10)	0.0071 (10)
C18	0.0459 (15)	0.0346 (13)	0.0306 (12)	0.0000 (11)	0.0167 (11)	0.0017 (10)
C19	0.0368 (13)	0.0239 (12)	0.0344 (13)	0.0038 (9)	0.0098 (10)	0.0028 (10)

O1—C2	1.349 (3)	C5—H5	0.9500
O1—H1O	0.846 (10)	C6—H6	0.9500
O2—C4	1.365 (3)	C7—H7A	0.9800
O2—C7	1.430 (3)	C7—H7B	0.9800
O3—C9	1.231 (2)	C7—H7C	0.9800
O4—C11	1.427 (3)	C8—H8	0.9500
O4—H4O	0.840 (10)	C9—C10	1.529 (3)
O5—C12	1.219 (3)	C10—C11	1.519 (3)
O6—C12	1.349 (2)	C10—H10	1.0000
O6—C13	1.446 (2)	C11—H11A	0.9900
N1—C8	1.291 (3)	C11—H11B	0.9900
N1—N2	1.388 (2)	C13—C14	1.505 (3)
N2—C9	1.332 (3)	C13—H13A	0.9900
N2—H2N	0.857 (10)	C13—H13B	0.9900
N3—C12	1.351 (3)	C14—C19	1.389 (3)
N3—C10	1.463 (3)	C14—C15	1.393 (3)
N3—H3N	0.861 (10)	C15—C16	1.385 (4)
C1—C6	1.404 (3)	C15—H15	0.9500
C1—C2	1.410 (3)	C16—C17	1.376 (4)
C1—C8	1.455 (3)	C16—H16	0.9500
C2—C3	1.398 (3)	C17—C18	1.391 (4)
C3—C4	1.388 (3)	C17—H17	0.9500
C3—H3	0.9500	C18—C19	1.387 (3)
C4—C5	1.396 (3)	C18—H18	0.9500
C5—C6	1.366 (3)	C19—H19	0.9500
C2—O1—H1O	107 (2)	N2—C9—C10	115.08 (16)
C4—O2—C7	117.93 (18)	N3—C10—C11	111.51 (16)
C11—O4—H4O	107 (2)	N3—C10—C9	110.83 (16)
C12—O6—C13	114.04 (16)	C11—C10—C9	109.62 (16)
C8—N1—N2	114.69 (18)	N3—C10—H10	108.3
C9—N2—N1	119.74 (17)	C11—C10—H10	108.3
C9—N2—H2N	120.9 (19)	C9—C10—H10	108.3
N1—N2—H2N	119.3 (18)	O4—C11—C10	110.37 (17)
C12—N3—C10	118.55 (17)	O4—C11—H11A	109.6
C12—N3—H3N	120.1 (17)	C10—C11—H11A	109.6
C10—N3—H3N	120.6 (18)	O4—C11—H11B	109.6
C6—C1—C2	117.9 (2)	C10—C11—H11B	109.6
C6—C1—C8	119.0 (2)	H11A—C11—H11B	108.1
C2—C1—C8	123.06 (19)	O5—C12—O6	124.06 (19)
O1—C2—C3	117.29 (19)	O5—C12—N3	124.77 (19)
O1—C2—C1	122.32 (19)	O6—C12—N3	111.17 (17)
C3—C2—C1	120.38 (19)	O6—C13—C14	108.60 (18)
C4—C3—C2	119.7 (2)	O6—C13—H13A	110.0
C4—C3—H3	120.2	C14—C13—H13A	110.0
C2—C3—H3	120.2	O6—C13—H13B	110.0
O2—C4—C3	123.9 (2)	C14—C13—H13B	110.0
O2—C4—C5	115.7 (2)	H13A—C13—H13B	108.4
C3—C4—C5	120.4 (2)	C19—C14—C15	118.5 (2)
C6—C5—C4	119.6 (2)	C19—C14—C13	121.8 (2)
C6—C5—H5	120.2	C15—C14—C13	119.6 (2)
C4—C5—H5	120.2	C16—C15—C14	120.6 (2)
C5—C6—C1	121.9 (2)	C16—C15—H15	119.7
C5—C6—H6	119.1	C14—C15—H15	119.7
C1—C6—H6	119.1	C17—C16—C15	120.4 (2)
O2—C7—H7A	109.5	C17—C16—H16	119.8
O2—C7—H7B	109.5	C15—C16—H16	119.8
H7A—C7—H7B	109.5	C16—C17—C18	119.7 (2)
O2—C7—H7C	109.5	C16—C17—H17	120.2
H7A—C7—H7C	109.5	C18—C17—H17	120.2
H7B—C7—H7C	109.5	C19—C18—C17	119.9 (2)
N1—C8—C1	120.96 (19)	C19—C18—H18	120.1
N1—C8—H8	119.5	C17—C18—H18	120.1
C1—C8—H8	119.5	C18—C19—C14	120.9 (2)
O3—C9—N2	124.50 (19)	C18—C19—H19	119.6
O3—C9—C10	120.36 (19)	C14—C19—H19	119.6
C8—N1—N2—C9	−167.97 (19)	C12—N3—C10—C9	−154.94 (18)
C6—C1—C2—O1	−178.4 (2)	O3—C9—C10—N3	−112.2 (2)
C8—C1—C2—O1	3.3 (3)	N2—C9—C10—N3	70.4 (2)
C6—C1—C2—C3	1.8 (3)	O3—C9—C10—C11	11.3 (3)
C8—C1—C2—C3	−176.6 (2)	N2—C9—C10—C11	−166.09 (17)
O1—C2—C3—C4	179.26 (19)	N3—C10—C11—O4	−172.47 (16)
C1—C2—C3—C4	−0.9 (3)	C9—C10—C11—O4	64.4 (2)
C7—O2—C4—C3	−1.2 (3)	C13—O6—C12—O5	0.5 (3)
C7—O2—C4—C5	178.6 (2)	C13—O6—C12—N3	179.84 (18)
C2—C3—C4—O2	179.4 (2)	C10—N3—C12—O5	−6.3 (3)
C2—C3—C4—C5	−0.3 (3)	C10—N3—C12—O6	174.38 (16)
O2—C4—C5—C6	−179.1 (2)	C12—O6—C13—C14	176.21 (18)
C3—C4—C5—C6	0.7 (3)	O6—C13—C14—C19	−45.1 (3)
C4—C5—C6—C1	0.3 (4)	O6—C13—C14—C15	139.2 (2)
C2—C1—C6—C5	−1.5 (3)	C19—C14—C15—C16	−2.2 (4)
C8—C1—C6—C5	176.9 (2)	C13—C14—C15—C16	173.6 (2)
N2—N1—C8—C1	177.31 (18)	C14—C15—C16—C17	1.1 (4)
C6—C1—C8—N1	−178.7 (2)	C15—C16—C17—C18	1.0 (4)
C2—C1—C8—N1	−0.4 (3)	C16—C17—C18—C19	−2.0 (4)
N1—N2—C9—O3	−2.6 (3)	C17—C18—C19—C14	0.8 (4)
N1—N2—C9—C10	174.73 (17)	C15—C14—C19—C18	1.2 (4)
C12—N3—C10—C11	82.6 (2)	C13—C14—C19—C18	−174.5 (2)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.85 (2)	1.91 (2)	2.667 (3)	149 (3)
N2—H2n···O4i	0.857 (18)	1.894 (18)	2.742 (2)	170 (2)
N3—H3n···O5ii	0.860 (18)	2.175 (17)	3.013 (2)	165 (2)
O4—H4o···O3iii	0.838 (15)	1.766 (16)	2.594 (2)	169 (3)
C7—H7c···Cg1ii	0.98	2.67	3.565 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.85 (2)	1.91 (2)	2.667 (3)	149 (3)
N2—H2n⋯O4i	0.86 (2)	1.89 (2)	2.742 (2)	170 (2)
N3—H3n⋯O5ii	0.86 (2)	2.18 (2)	3.013 (2)	165 (2)
O4—H4o⋯O3iii	0.84 (2)	1.77 (2)	2.594 (2)	169 (3)
C7—H7c⋯Cg1ii	0.98	2.67	3.565 (3)	151

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