tert-Butyl N-{(1S)-1-[(2,4-dihy-droxy-benzyl-idene)hydrazinecarbon-yl]-2-hy-droxy-eth-yl}carbamate ethanol monosolvate.

The mol-ecule of the title ethanol solvate, C(15)H(21)N(3)O(6)·C(2)H(6)O, adopts a curved shape; the conformation about the imine bond [N=N = 1.287 (3) Å] is E. The amide residues occupy positions almost orthogonal to each other [dihedral angle = 85.7 (2)°]. In the crystal, a network of O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds leads to the formation of supra-molecular arrays in the ab plane with the ethanol mol-ecules lying to the periphery on either side. Disorder in the solvent ethanol mol-ecule was evident with two positions being resolved for the C atoms [site occupancy of the major component = 0.612 (10)].

Related literature

For background to 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 background to N-acyl­hydrazone derivatives from l-serine for anti-tumour testing, see: Rollas & Küçükgüzel (2007 ▶); Terzioğlu & Gürsoy (2003 ▶). For related structures, see: Pinheiro et al. (2010 ▶); de Souza et al. (2010 ▶).

Experimental

Crystal data

C15H21N3O6·C2H6O

M = 385.42

Monoclinic,

a = 17.4054 (4) Å

b = 8.7266 (2) Å

c = 15.0105 (4) Å

β = 122.219 (2)°

V = 1928.87 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 120 K

0.16 × 0.14 × 0.06 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.897, T max = 1.000

19885 measured reflections

2369 independent reflections

2303 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.099

S = 1.06

2369 reflections

271 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.33 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/S1600536811003795/hb5793sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003795/hb5793Isup2.hkl

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

C15H21N3O6·C2H6O	F(000) = 824
Mr = 385.42	Dx = 1.327 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 4327 reflections
a = 17.4054 (4) Å	θ = 2.9–27.5°
b = 8.7266 (2) Å	µ = 0.10 mm−1
c = 15.0105 (4) Å	T = 120 K
β = 122.219 (2)°	Block, colourless
V = 1928.87 (8) Å3	0.16 × 0.14 × 0.06 mm
Z = 4

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	2369 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode CCD	2303 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −11→11
Tmin = 0.897, Tmax = 1.000	l = −19→19
19885 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0606P)2 + 1.0679P] where P = (Fo2 + 2Fc2)/3
2369 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.61 e Å−3
7 restraints	Δρmin = −0.33 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	Occ. (<1)
O1	−0.01014 (11)	0.6314 (2)	0.76103 (14)	0.0306 (4)
H1o	0.0421 (13)	0.674 (4)	0.796 (2)	0.046*
O2	−0.30367 (9)	0.6766 (2)	0.69839 (12)	0.0259 (3)
H2o	−0.3330 (19)	0.728 (3)	0.717 (2)	0.039*
O3	0.27544 (10)	0.67257 (19)	0.95473 (12)	0.0251 (3)
O4	0.39535 (10)	0.8716 (2)	0.89717 (11)	0.0266 (3)
H4o	0.3474 (13)	0.853 (4)	0.8402 (14)	0.040*
O5	0.39849 (11)	0.7949 (2)	1.22519 (13)	0.0333 (4)
O6	0.53955 (10)	0.7219 (2)	1.26444 (11)	0.0267 (4)
N1	0.11580 (11)	0.8217 (2)	0.89800 (13)	0.0219 (4)
N2	0.20132 (11)	0.8878 (2)	0.95418 (14)	0.0221 (4)
H2n	0.2041 (18)	0.9793 (16)	0.976 (2)	0.027*
N3	0.44121 (11)	0.8160 (2)	1.10779 (13)	0.0206 (4)
H3n	0.4884 (12)	0.824 (3)	1.104 (2)	0.025*
C1	−0.04087 (13)	0.8468 (3)	0.83868 (15)	0.0209 (4)
C2	−0.06834 (13)	0.7128 (2)	0.77631 (15)	0.0204 (4)
C3	−0.15725 (13)	0.6607 (3)	0.72779 (15)	0.0214 (4)
H3	−0.1759	0.5722	0.6843	0.026*
C4	−0.21852 (13)	0.7390 (3)	0.74340 (15)	0.0205 (4)
C5	−0.19388 (13)	0.8728 (3)	0.80333 (16)	0.0237 (4)
H5	−0.2368	0.9262	0.8124	0.028*
C6	−0.10573 (14)	0.9263 (3)	0.84935 (16)	0.0230 (4)
H6	−0.0888	1.0186	0.8889	0.028*
C7	0.05209 (14)	0.9025 (3)	0.89384 (16)	0.0218 (4)
H7	0.0660	0.9998	0.9273	0.026*
C8	0.27609 (13)	0.8076 (2)	0.97909 (15)	0.0193 (4)
C9	0.36197 (12)	0.9053 (2)	1.03518 (15)	0.0192 (4)
H9	0.3536	0.9876	1.0756	0.023*
C10	0.37737 (13)	0.9809 (3)	0.95365 (16)	0.0232 (4)
H10A	0.3228	1.0408	0.9035	0.028*
H10B	0.4292	1.0528	0.9900	0.028*
C11	0.45577 (14)	0.7797 (3)	1.20233 (17)	0.0227 (4)
C12	0.57832 (15)	0.6887 (3)	1.37713 (16)	0.0303 (5)
C13	0.52980 (18)	0.5534 (4)	1.3883 (2)	0.0379 (6)
H13A	0.4669	0.5818	1.3629	0.057*
H13B	0.5608	0.5234	1.4626	0.057*
H13C	0.5302	0.4672	1.3467	0.057*
C14	0.5758 (2)	0.8318 (4)	1.4328 (2)	0.0445 (7)
H14A	0.5988	0.9190	1.4126	0.067*
H14B	0.6139	0.8166	1.5092	0.067*
H14C	0.5132	0.8521	1.4127	0.067*
C15	0.67546 (16)	0.6455 (4)	1.41358 (19)	0.0429 (7)
H15A	0.6751	0.5548	1.3748	0.064*
H15B	0.7093	0.6227	1.4891	0.064*
H15C	0.7045	0.7309	1.4003	0.064*
O7	0.27404 (12)	0.3530 (2)	0.28565 (16)	0.0403 (4)
H7o	0.292 (3)	0.443 (2)	0.304 (3)	0.060*
C16	0.3454 (10)	0.245 (2)	0.3050 (12)	0.0525 (8)	0.612 (10)
H16A	0.3995	0.3029	0.3182	0.063*	0.612 (10)
H16B	0.3241	0.1816	0.2413	0.063*	0.612 (10)
C17	0.3713 (5)	0.1452 (9)	0.3940 (6)	0.0495 (14)	0.612 (10)
H17A	0.3926	0.2073	0.4574	0.074*	0.612 (10)
H17B	0.4200	0.0765	0.4046	0.074*	0.612 (10)
H17C	0.3186	0.0845	0.3801	0.074*	0.612 (10)
C18	0.3420 (13)	0.249 (3)	0.3037 (18)	0.0525 (8)	0.388 (10)
H18A	0.3795	0.2940	0.2789	0.063*	0.388 (10)
H18B	0.3133	0.1547	0.2621	0.063*	0.388 (10)
C19	0.4010 (8)	0.2074 (14)	0.4154 (9)	0.0495 (14)	0.388 (10)
H19A	0.4427	0.2922	0.4538	0.074*	0.388 (10)
H19B	0.4360	0.1155	0.4219	0.074*	0.388 (10)
H19C	0.3637	0.1869	0.4450	0.074*	0.388 (10)

	U11	U22	U33	U12	U13	U23
O1	0.0239 (7)	0.0322 (9)	0.0381 (9)	−0.0014 (7)	0.0182 (7)	−0.0059 (7)
O2	0.0155 (7)	0.0351 (9)	0.0283 (8)	−0.0018 (6)	0.0124 (6)	−0.0029 (7)
O3	0.0231 (7)	0.0197 (7)	0.0301 (7)	−0.0008 (6)	0.0126 (6)	−0.0001 (6)
O4	0.0205 (7)	0.0384 (9)	0.0223 (7)	0.0012 (7)	0.0123 (6)	0.0005 (7)
O5	0.0274 (8)	0.0464 (10)	0.0352 (8)	0.0105 (8)	0.0227 (7)	0.0136 (8)
O6	0.0211 (7)	0.0410 (10)	0.0188 (7)	0.0088 (7)	0.0111 (6)	0.0070 (7)
N1	0.0152 (7)	0.0239 (9)	0.0251 (8)	−0.0026 (7)	0.0097 (7)	−0.0006 (7)
N2	0.0169 (8)	0.0203 (9)	0.0271 (8)	−0.0025 (7)	0.0104 (7)	−0.0017 (7)
N3	0.0154 (7)	0.0261 (9)	0.0205 (8)	0.0034 (7)	0.0097 (6)	0.0031 (7)
C1	0.0180 (8)	0.0233 (10)	0.0208 (8)	0.0006 (8)	0.0100 (7)	0.0034 (8)
C2	0.0187 (8)	0.0238 (11)	0.0196 (8)	0.0019 (8)	0.0109 (7)	0.0035 (8)
C3	0.0193 (9)	0.0250 (10)	0.0192 (8)	−0.0005 (8)	0.0098 (7)	−0.0001 (8)
C4	0.0147 (8)	0.0272 (10)	0.0188 (8)	0.0007 (8)	0.0084 (7)	0.0042 (8)
C5	0.0188 (9)	0.0300 (12)	0.0246 (9)	0.0041 (8)	0.0132 (8)	0.0026 (8)
C6	0.0218 (9)	0.0245 (10)	0.0247 (9)	0.0009 (8)	0.0137 (8)	−0.0004 (8)
C7	0.0199 (9)	0.0218 (10)	0.0231 (9)	−0.0018 (8)	0.0109 (8)	0.0000 (8)
C8	0.0184 (9)	0.0201 (10)	0.0200 (8)	0.0001 (8)	0.0106 (7)	0.0035 (7)
C9	0.0158 (8)	0.0190 (9)	0.0216 (8)	0.0009 (7)	0.0091 (7)	0.0003 (7)
C10	0.0175 (9)	0.0248 (10)	0.0265 (10)	−0.0001 (8)	0.0113 (8)	0.0034 (8)
C11	0.0200 (9)	0.0255 (10)	0.0230 (9)	0.0020 (8)	0.0116 (8)	0.0028 (8)
C12	0.0291 (11)	0.0417 (13)	0.0195 (9)	0.0073 (10)	0.0127 (8)	0.0072 (9)
C13	0.0358 (12)	0.0448 (15)	0.0369 (13)	0.0103 (11)	0.0219 (11)	0.0141 (11)
C14	0.0570 (17)	0.0470 (16)	0.0246 (11)	0.0099 (14)	0.0184 (12)	0.0012 (11)
C15	0.0255 (11)	0.070 (2)	0.0263 (11)	0.0118 (12)	0.0096 (9)	0.0146 (12)
O7	0.0275 (8)	0.0350 (10)	0.0458 (10)	0.0023 (8)	0.0110 (8)	0.0098 (9)
C16	0.0547 (19)	0.0421 (17)	0.0537 (18)	0.0098 (15)	0.0241 (16)	0.0009 (14)
C17	0.047 (3)	0.045 (4)	0.054 (3)	0.014 (2)	0.025 (3)	0.012 (3)
C18	0.0547 (19)	0.0421 (17)	0.0537 (18)	0.0098 (15)	0.0241 (16)	0.0009 (14)
C19	0.047 (3)	0.045 (4)	0.054 (3)	0.014 (2)	0.025 (3)	0.012 (3)

O1—C2	1.353 (3)	C9—H9	1.0000
O1—H1o	0.86 (3)	C10—H10A	0.9900
O2—C4	1.372 (2)	C10—H10B	0.9900
O2—H2o	0.83 (3)	C12—C13	1.512 (4)
O3—C8	1.232 (3)	C12—C14	1.516 (4)
O4—C10	1.417 (3)	C12—C15	1.521 (3)
O4—H4o	0.833 (10)	C13—H13A	0.9800
O5—C11	1.222 (3)	C13—H13B	0.9800
O6—C11	1.342 (2)	C13—H13C	0.9800
O6—C12	1.478 (2)	C14—H14A	0.9800
N1—C7	1.287 (3)	C14—H14B	0.9800
N1—N2	1.386 (2)	C14—H14C	0.9800
N2—C8	1.343 (3)	C15—H15A	0.9800
N2—H2n	0.855 (10)	C15—H15B	0.9800
N3—C11	1.340 (3)	C15—H15C	0.9800
N3—C9	1.447 (2)	O7—C18	1.400 (9)
N3—H3n	0.86 (3)	O7—C16	1.460 (8)
C1—C6	1.405 (3)	O7—H7O	0.842 (10)
C1—C2	1.412 (3)	C16—C17	1.450 (12)
C1—C7	1.453 (3)	C16—H16A	0.9900
C2—C3	1.389 (3)	C16—H16B	0.9900
C3—C4	1.388 (3)	C17—H17A	0.9800
C3—H3	0.9500	C17—H17B	0.9800
C4—C5	1.394 (3)	C17—H17C	0.9800
C5—C6	1.385 (3)	C18—C19	1.47 (2)
C5—H5	0.9500	C18—H18A	0.9900
C6—H6	0.9500	C18—H18B	0.9900
C7—H7	0.9500	C19—H19A	0.9800
C8—C9	1.525 (3)	C19—H19B	0.9800
C9—C10	1.535 (3)	C19—H19C	0.9800
C2—O1—H1o	109 (3)	O5—C11—N3	123.4 (2)
C4—O2—H2o	108 (2)	O6—C11—N3	110.28 (17)
C10—O4—H4o	109 (2)	O6—C12—C13	109.8 (2)
C11—O6—C12	122.20 (16)	O6—C12—C14	109.9 (2)
C7—N1—N2	114.81 (18)	C13—C12—C14	113.6 (2)
C8—N2—N1	121.30 (18)	O6—C12—C15	101.66 (17)
C8—N2—H2n	122.1 (18)	C13—C12—C15	110.2 (2)
N1—N2—H2n	116.4 (18)	C14—C12—C15	111.0 (2)
C11—N3—C9	119.41 (16)	C12—C13—H13A	109.5
C11—N3—H3n	116.2 (18)	C12—C13—H13B	109.5
C9—N3—H3n	118.0 (19)	H13A—C13—H13B	109.5
C6—C1—C2	118.39 (18)	C12—C13—H13C	109.5
C6—C1—C7	119.2 (2)	H13A—C13—H13C	109.5
C2—C1—C7	122.35 (18)	H13B—C13—H13C	109.5
O1—C2—C3	117.67 (19)	C12—C14—H14A	109.5
O1—C2—C1	121.84 (18)	C12—C14—H14B	109.5
C3—C2—C1	120.49 (18)	H14A—C14—H14B	109.5
C2—C3—C4	119.5 (2)	C12—C14—H14C	109.5
C2—C3—H3	120.3	H14A—C14—H14C	109.5
C4—C3—H3	120.3	H14B—C14—H14C	109.5
O2—C4—C3	116.6 (2)	C12—C15—H15A	109.5
O2—C4—C5	121.99 (18)	C12—C15—H15B	109.5
C3—C4—C5	121.43 (18)	H15A—C15—H15B	109.5
C6—C5—C4	118.80 (19)	C12—C15—H15C	109.5
C6—C5—H5	120.6	H15A—C15—H15C	109.5
C4—C5—H5	120.6	H15B—C15—H15C	109.5
C5—C6—C1	121.4 (2)	C18—O7—C16	0(3)
C5—C6—H6	119.3	C18—O7—H7o	114 (3)
C1—C6—H6	119.3	C16—O7—H7o	114 (3)
N1—C7—C1	120.9 (2)	O7—C16—C17	112.6 (7)
N1—C7—H7	119.6	O7—C16—H16A	109.1
C1—C7—H7	119.6	C17—C16—H16A	109.1
O3—C8—N2	124.15 (19)	O7—C16—H16B	109.1
O3—C8—C9	123.30 (18)	C17—C16—H16B	109.1
N2—C8—C9	112.44 (18)	H16A—C16—H16B	107.8
N3—C9—C8	112.03 (17)	O7—C18—C19	112.6 (15)
N3—C9—C10	109.30 (16)	O7—C18—H18A	109.1
C8—C9—C10	109.66 (16)	C19—C18—H18A	109.1
N3—C9—H9	108.6	O7—C18—H18B	109.1
C8—C9—H9	108.6	C19—C18—H18B	109.1
C10—C9—H9	108.6	H18A—C18—H18B	107.8
O4—C10—C9	112.07 (18)	C18—C19—H19A	109.5
O4—C10—H10A	109.2	C18—C19—H19B	109.5
C9—C10—H10A	109.2	H19A—C19—H19B	109.5
O4—C10—H10B	109.2	C18—C19—H19C	109.5
C9—C10—H10B	109.2	H19A—C19—H19C	109.5
H10A—C10—H10B	107.9	H19B—C19—H19C	109.5
O5—C11—O6	126.34 (19)
C7—N1—N2—C8	169.49 (18)	N1—N2—C8—C9	176.62 (17)
C6—C1—C2—O1	179.01 (19)	C11—N3—C9—C8	−78.9 (2)
C7—C1—C2—O1	−2.6 (3)	C11—N3—C9—C10	159.32 (19)
C6—C1—C2—C3	−0.6 (3)	O3—C8—C9—N3	−33.9 (3)
C7—C1—C2—C3	177.78 (19)	N2—C8—C9—N3	149.72 (17)
O1—C2—C3—C4	178.56 (18)	O3—C8—C9—C10	87.7 (2)
C1—C2—C3—C4	−1.8 (3)	N2—C8—C9—C10	−88.7 (2)
C2—C3—C4—O2	−176.30 (18)	N3—C9—C10—O4	58.1 (2)
C2—C3—C4—C5	2.7 (3)	C8—C9—C10—O4	−65.0 (2)
O2—C4—C5—C6	177.85 (19)	C12—O6—C11—O5	−9.2 (4)
C3—C4—C5—C6	−1.1 (3)	C12—O6—C11—N3	172.7 (2)
C4—C5—C6—C1	−1.5 (3)	C9—N3—C11—O5	12.9 (4)
C2—C1—C6—C5	2.3 (3)	C9—N3—C11—O6	−168.91 (18)
C7—C1—C6—C5	−176.19 (19)	C11—O6—C12—C13	69.9 (3)
N2—N1—C7—C1	−179.27 (17)	C11—O6—C12—C14	−55.8 (3)
C6—C1—C7—N1	170.21 (19)	C11—O6—C12—C15	−173.4 (2)
C2—C1—C7—N1	−8.2 (3)	C18—O7—C16—C17	−98 (83)
N1—N2—C8—O3	0.3 (3)	C16—O7—C18—C19	52 (82)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.86 (3)	1.89 (3)	2.643 (3)	147 (3)
N2—H2n···O3i	0.86 (3)	1.91 (2)	2.760 (2)	171 (2)
O2—H2o···O5ii	0.83 (3)	1.86 (3)	2.669 (3)	165 (3)
N3—H3n···O4iii	0.86 (3)	2.08 (3)	2.926 (3)	173 (2)
O4—H4o···O7iv	0.83 (1)	1.94 (2)	2.761 (3)	167 (3)
O7—H7o···O2v	0.84 (1)	2.05 (2)	2.858 (2)	162 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.86 (3)	1.89 (3)	2.643 (3)	147 (3)
N2—H2n⋯O3i	0.86 (3)	1.91 (2)	2.760 (2)	171 (2)
O2—H2o⋯O5ii	0.83 (3)	1.86 (3)	2.669 (3)	165 (3)
N3—H3n⋯O4iii	0.86 (3)	2.08 (3)	2.926 (3)	173 (2)
O4—H4o⋯O7iv	0.83 (1)	1.94 (2)	2.761 (3)	167 (3)
O7—H7o⋯O2v	0.84 (1)	2.05 (2)	2.858 (2)	162 (4)

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