(S)-2-[(2R,3S)-2-Ammonio-3-hydr­oxy-3-(4-nitro­phen­yl)propanamido]-4-methyl­penta­noate monohydrate

Yang, K.-H.; Li, X.; Gong, J.-Z.; Fang, H.; Xu, W.-F.

doi:10.1107/S1600536808039056

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2447

doi:10.1107/S1600536808039056

Open

access

(S)-2-[(2R,3S)-2-Ammonio-3-hydroxy-3-(4-nitrophenyl)propanamido]-4-methylpentanoate monohydrate

Kang-Hui Yang,^a Xun Li,^a Jian-Zhi Gong,^a Hao Fang ^a and Wen-Fang Xu ^a ^*

^aInstitute of Medicinal Chemistry, School of Pharmacy, Shandong University, Ji'nan 250012, People's Republic of China
^*Correspondence e-mail: xuwenfsdu@yahoo.cn

(Received 30 October 2008; accepted 21 November 2008; online 26 November 2008)

The structure of the title compound, C₁₅H₂₁N₃O₆·H₂O, is of interest with respect to assumed anticancer activity. The title molecules are linked through intermolecular O—H⋯O hydrogen-bonded chains along the a axis. These chains are connected by intermolecular N—H⋯O hydrogen bonds through the crystallographic screw axis along [010], forming layers, which are stabilized by other N—H⋯O bonds with water O atoms as acceptors and O—H⋯O bonds with water H atoms as donors. The H atoms of the protonated amino cation are also involved in intermolecular N—H⋯O bonding interactions.

Related literature

For various medicinal agents similar to the title compound, see: Shinagawa et al. (1987 ); Shin & Pyo (1984 ). For anti-cancer and anti-inflammatory biological properties, see: Aozuka et al. (2004 ). For aminopeptidase N (APN/CD13) inhibitors, see: Xu & Li (2005 ). For the synthesis of the starting material, see: Testa et al. (2004 ).

Experimental

Crystal data

C₁₅H₂₁N₃O₆·H₂O
M_r = 357.36
Monoclinic, P 2₁
a = 8.9787 (7) Å
b = 6.7850 (5) Å
c = 14.7148 (11) Å
β = 95.362 (5)°
V = 892.51 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 (2) K
0.50 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.949, T_max = 0.984
8245 measured reflections
2254 independent reflections
1853 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.104
S = 1.04
2254 reflections
243 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7W⋯O5	0.92	1.87	2.679 (2)	146
O7—H8W⋯O4ⁱ	0.88	1.96	2.734 (3)	146
N2—H2B⋯O3ⁱⁱ	0.87 (3)	1.99 (3)	2.854 (3)	172 (3)
O3—H4⋯O5ⁱⁱⁱ	0.82	1.79	2.612 (2)	175
N3—H3A⋯O7ⁱ	0.86	2.08	2.914 (3)	163
N2—H2C⋯O6ⁱ	0.99 (3)	1.96 (3)	2.811 (3)	143 (3)
N2—H2A⋯O7	0.95 (3)	1.89 (3)	2.801 (2)	158 (3)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 and SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039056/si2128sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039056/si2128Isup2.hkl

checkCIF report

Comment top

The 2-amino-1-hydroxy carboxylic acids and 1-amino-2-hydroxy carboxylic acids are important precursor and scaffold of various medicinal agents (Shinagawa et al., 1987). It was reported that many of their derivatives exhibit anti-cancer and anti-inflammatory properties (Aozuka et al., 2004). Our lab has been engaged in developing 1-amino-2-hydroxy carboxylic acids derivatives as Aminopeptidase N (APN/CD13) inhibitors (Xu & Li, 2005). One of the aims of the projects is to use different amino acid coupled with 1-amino-2-hydroxy carboxylic acids scaffold, the resulting target derivatives are hope to have antitumor activities. Both the title compound (Fig. 1) and the reported chloramphenicol base have the amino-hydroxy-nitrophenyl scaffold in their structures (Shin & Pyo, 1984). In the molecule, the bond length of C8–N2 is 1.489 (3) Å, which is slightly longer than that of the C8–N2 (1.473 (7) Å) in the chloramphenicol base. This is probably due to the electrostatic attractions between the carboxyl anion and the protonated amino cation. The title molecules are linked through intermolecular O—H···O hydrogen bonded chains along the a axis (Table 1, Fig. 2). These chains are connected by intermolecular N—H···O hydrogen bonds through the crystallographic screw axis along the [0 1 0] direction to form layers which are stabilized by other N—H···O bonds with water oxygen atoms as acceptors and O—H···O bonds with water hydrogen atoms as donors.The H atoms of the protonated amino cation were also involved in intermolecular N—H···O bonding interactions.

Related literature top

For various medicinal agents similar to the title compound, see: Shinagawa et al. (1987); Shin & Pyo (1984). For anti-cancer and anti-inflammatory biological properties, see: Aozuka et al. (2004). For aminopeptidase N (APN/CD13) inhibitors, see: Xu & Li (2005). For the synthesis of the starting material, see: Testa et al. (2004).

Experimental top

The starting material, (2R,3S)-2-(tert-butoxycarbonylamino) -3-hydroxy-3-(4-nitrophenyl) propanoic acid, prepared according to the literature (Testa et al., 2004), was coupled with L-leucine methyl ester by using dicyclohexylcarbodiimide (DCC) and 1-hydroxybenzotriazole (HOBt). Finally, the title compound was yielded by hydrolyzing in NaOH and then deprotecting Boc group with hydrochloride. Crystals appropriate for data collection were obtained by slow evaporation of the solid in methanol at room temperature. Yield 40%, m.p. 481 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005) and SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of the title molecules, showing 30% probability displacement ellipsoids and the numbering scheme of non-hydrogen atoms.
	Fig. 2. A view of the unit cell of the title compound, showing intermolecular hydrogen bonds as dashed lines.

(S)-2-[(2R,3S)-2-Ammonio-3-hydroxy-3-(4-nitrophenyl)propanamido]-4-methylpentanoate monohydrate top

Crystal data top

C₁₅H₂₁N₃O₆·H₂O	F(000) = 380
M_r = 357.36	D_x = 1.330 Mg m⁻³
Monoclinic, P2₁	Melting point = 556.2–558.6 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 8.9787 (7) Å	Cell parameters from 2639 reflections
b = 6.7850 (5) Å	θ = 2.8–24.2°
c = 14.7148 (11) Å	µ = 0.11 mm⁻¹
β = 95.362 (5)°	T = 296 K
V = 892.51 (12) Å³	Prism, colourless
Z = 2	0.50 × 0.20 × 0.15 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2254 independent reflections
Radiation source: fine-focus sealed tube	1853 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.949, T_max = 0.984	k = −8→8
8245 measured reflections	l = −19→18

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.059P)² + 0.0778P] where P = (F_o² + 2F_c²)/3
2254 reflections	(Δ/σ)_max < 0.001
243 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₅H₂₁N₃O₆·H₂O	V = 892.51 (12) Å³
M_r = 357.36	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.9787 (7) Å	µ = 0.11 mm⁻¹
b = 6.7850 (5) Å	T = 296 K
c = 14.7148 (11) Å	0.50 × 0.20 × 0.15 mm
β = 95.362 (5)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2254 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1853 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.984	R_int = 0.028
8245 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.19 e Å⁻³
2254 reflections	Δρ_min = −0.16 e Å⁻³
243 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1171 (3)	1.0193 (5)	0.8450 (2)	0.0593 (8)
C2	0.1386 (3)	1.1114 (5)	0.7646 (2)	0.0576 (8)
H2	0.1620	1.2449	0.7637	0.069*
C3	0.1250 (3)	1.0037 (4)	0.68503 (19)	0.0466 (6)
H10	0.1388	1.0647	0.6298	0.056*
C4	0.0906 (2)	0.8025 (4)	0.68693 (16)	0.0350 (5)
C5	0.0699 (3)	0.7141 (5)	0.76921 (18)	0.0487 (7)
H5	0.0466	0.5806	0.7708	0.058*
C6	0.0834 (3)	0.8219 (6)	0.8498 (2)	0.0627 (9)
H6	0.0700	0.7624	0.9053	0.075*
C7	0.0792 (2)	0.6835 (4)	0.59945 (16)	0.0320 (5)
H7	0.0586	0.5457	0.6137	0.038*
C8	0.2268 (2)	0.6944 (3)	0.55531 (14)	0.0303 (5)
H8	0.2570	0.8326	0.5509	0.036*
C9	0.3482 (2)	0.5812 (4)	0.61333 (15)	0.0313 (5)
C10	0.7060 (2)	0.5166 (4)	0.64655 (17)	0.0386 (6)
C11	0.5895 (2)	0.6028 (4)	0.70569 (15)	0.0368 (5)
H11	0.5533	0.4984	0.7441	0.044*
C12	0.6643 (3)	0.7644 (5)	0.76667 (18)	0.0469 (6)
H12A	0.7440	0.7047	0.8064	0.056*
H12B	0.7100	0.8583	0.7280	0.056*
C13	0.5625 (4)	0.8776 (7)	0.8260 (2)	0.0707 (10)
H13	0.4790	0.9317	0.7860	0.085*
C14	0.6501 (6)	1.0509 (8)	0.8721 (3)	0.1067 (16)
H14A	0.7269	1.0011	0.9159	0.160*
H14B	0.5832	1.1331	0.9025	0.160*
H14C	0.6950	1.1266	0.8268	0.160*
C15	0.4992 (5)	0.7477 (10)	0.8948 (3)	0.1045 (17)
H15A	0.5792	0.6944	0.9353	0.157*
H15B	0.4442	0.6420	0.8640	0.157*
H15C	0.4337	0.8232	0.9292	0.157*
N1	0.1333 (4)	1.1348 (8)	0.9301 (3)	0.0933 (13)
N2	0.2080 (2)	0.6066 (3)	0.46217 (14)	0.0345 (4)
N3	0.46309 (18)	0.6869 (3)	0.64893 (13)	0.0346 (4)
H3A	0.4634	0.8115	0.6381	0.042*
O1	0.1562 (6)	1.3125 (7)	0.9239 (3)	0.1463 (17)
O2	0.1267 (4)	1.0520 (8)	1.0013 (2)	0.1297 (16)
O3	−0.03561 (16)	0.7538 (3)	0.53411 (11)	0.0371 (4)
H4	−0.1147	0.6988	0.5420	0.056*
O4	0.33299 (19)	0.4031 (3)	0.62517 (14)	0.0482 (5)
O5	0.71194 (18)	0.5906 (3)	0.56790 (12)	0.0471 (5)
O6	0.7901 (2)	0.3852 (3)	0.67915 (14)	0.0548 (5)
O7	0.50705 (17)	0.5833 (3)	0.42343 (12)	0.0410 (4)
H7W	0.5421	0.5886	0.4840	0.086 (12)*
H8W	0.5327	0.6792	0.3873	0.071 (10)*
H2B	0.154 (3)	0.500 (5)	0.4578 (19)	0.045 (8)*
H2C	0.162 (4)	0.702 (5)	0.416 (2)	0.055 (8)*
H2A	0.305 (4)	0.564 (5)	0.448 (2)	0.060 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0459 (16)	0.076 (2)	0.0564 (18)	0.0056 (15)	0.0037 (13)	−0.0238 (17)
C2	0.0583 (18)	0.0473 (16)	0.0666 (19)	0.0060 (14)	0.0025 (14)	−0.0134 (16)
C3	0.0478 (15)	0.0390 (14)	0.0530 (16)	0.0044 (12)	0.0046 (12)	−0.0038 (13)
C4	0.0207 (10)	0.0405 (13)	0.0438 (13)	0.0056 (9)	0.0035 (9)	−0.0001 (11)
C5	0.0405 (14)	0.0568 (18)	0.0502 (15)	−0.0030 (12)	0.0117 (11)	0.0034 (14)
C6	0.0536 (17)	0.092 (3)	0.0436 (16)	−0.0035 (18)	0.0122 (13)	0.0009 (17)
C7	0.0198 (9)	0.0319 (10)	0.0443 (12)	0.0009 (9)	0.0030 (8)	0.0040 (10)
C8	0.0212 (10)	0.0278 (10)	0.0420 (12)	−0.0012 (8)	0.0041 (8)	−0.0011 (10)
C9	0.0234 (10)	0.0322 (12)	0.0389 (11)	0.0043 (9)	0.0063 (8)	−0.0008 (10)
C10	0.0236 (10)	0.0444 (14)	0.0469 (14)	−0.0012 (10)	−0.0007 (9)	−0.0097 (11)
C11	0.0246 (10)	0.0462 (14)	0.0394 (12)	0.0048 (10)	0.0019 (8)	0.0056 (11)
C12	0.0376 (13)	0.0602 (16)	0.0419 (13)	0.0076 (12)	−0.0014 (10)	−0.0077 (13)
C13	0.0663 (19)	0.099 (3)	0.0454 (16)	0.034 (2)	−0.0050 (14)	−0.0190 (18)
C14	0.143 (4)	0.097 (3)	0.079 (3)	0.024 (3)	−0.001 (3)	−0.040 (3)
C15	0.084 (3)	0.170 (5)	0.064 (2)	0.017 (3)	0.0297 (19)	−0.009 (3)
N1	0.085 (2)	0.126 (4)	0.069 (2)	0.004 (2)	0.0054 (17)	−0.041 (2)
N2	0.0247 (10)	0.0361 (11)	0.0433 (11)	−0.0023 (9)	0.0057 (8)	−0.0012 (10)
N3	0.0223 (9)	0.0356 (10)	0.0458 (11)	−0.0005 (8)	0.0027 (7)	0.0025 (9)
O1	0.222 (5)	0.107 (3)	0.105 (3)	0.002 (3)	−0.009 (3)	−0.062 (3)
O2	0.155 (3)	0.180 (4)	0.0575 (16)	−0.041 (3)	0.0267 (18)	−0.043 (2)
O3	0.0214 (7)	0.0398 (9)	0.0495 (9)	0.0015 (7)	0.0012 (6)	0.0023 (8)
O4	0.0373 (9)	0.0318 (9)	0.0742 (12)	0.0033 (8)	−0.0014 (8)	0.0039 (9)
O5	0.0272 (8)	0.0707 (13)	0.0439 (10)	0.0003 (9)	0.0073 (7)	−0.0007 (10)
O6	0.0444 (10)	0.0550 (12)	0.0641 (12)	0.0190 (10)	0.0003 (9)	−0.0045 (10)
O7	0.0323 (8)	0.0407 (9)	0.0507 (10)	−0.0021 (8)	0.0070 (7)	0.0013 (9)

Geometric parameters (Å, º) top

C1—C2	1.368 (5)	C11—C12	1.532 (4)
C1—C6	1.376 (5)	C11—H11	0.9800
C1—N1	1.473 (4)	C12—C13	1.528 (4)
C2—C3	1.376 (4)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C3—C4	1.401 (4)	C13—C15	1.494 (6)
C3—H10	0.9300	C13—C14	1.537 (6)
C4—C5	1.379 (3)	C13—H13	0.9800
C4—C7	1.515 (3)	C14—H14A	0.9600
C5—C6	1.388 (4)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—O3	1.424 (3)	C15—H15B	0.9600
C7—C8	1.531 (3)	C15—H15C	0.9600
C7—H7	0.9800	N1—O2	1.195 (6)
C8—N2	1.489 (3)	N1—O1	1.228 (7)
C8—C9	1.528 (3)	N2—H2B	0.87 (3)
C8—H8	0.9800	N2—H2C	0.99 (3)
C9—O4	1.231 (3)	N2—H2A	0.95 (3)
C9—N3	1.323 (3)	N3—H3A	0.8600
C10—O6	1.236 (3)	O3—H4	0.8200
C10—O5	1.267 (3)	O7—H7W	0.9174
C10—C11	1.538 (3)	O7—H8W	0.8845
C11—N3	1.461 (3)

C2—C1—C6	122.5 (3)	C12—C11—H11	109.3
C2—C1—N1	118.8 (4)	C10—C11—H11	109.3
C6—C1—N1	118.6 (4)	C13—C12—C11	116.2 (2)
C1—C2—C3	119.0 (3)	C13—C12—H12A	108.2
C1—C2—H2	120.5	C11—C12—H12A	108.2
C3—C2—H2	120.5	C13—C12—H12B	108.2
C2—C3—C4	120.2 (3)	C11—C12—H12B	108.2
C2—C3—H10	119.9	H12A—C12—H12B	107.4
C4—C3—H10	119.9	C15—C13—C12	112.1 (4)
C5—C4—C3	119.3 (3)	C15—C13—C14	111.3 (3)
C5—C4—C7	120.7 (2)	C12—C13—C14	109.2 (3)
C3—C4—C7	120.0 (2)	C15—C13—H13	108.1
C4—C5—C6	120.8 (3)	C12—C13—H13	108.1
C4—C5—H5	119.6	C14—C13—H13	108.1
C6—C5—H5	119.6	C13—C14—H14A	109.5
C1—C6—C5	118.1 (3)	C13—C14—H14B	109.5
C1—C6—H6	120.9	H14A—C14—H14B	109.5
C5—C6—H6	120.9	C13—C14—H14C	109.5
O3—C7—C4	112.48 (18)	H14A—C14—H14C	109.5
O3—C7—C8	107.33 (17)	H14B—C14—H14C	109.5
C4—C7—C8	110.03 (18)	C13—C15—H15A	109.5
O3—C7—H7	109.0	C13—C15—H15B	109.5
C4—C7—H7	109.0	H15A—C15—H15B	109.5
C8—C7—H7	109.0	C13—C15—H15C	109.5
N2—C8—C9	109.07 (18)	H15A—C15—H15C	109.5
N2—C8—C7	110.07 (17)	H15B—C15—H15C	109.5
C9—C8—C7	109.85 (18)	O2—N1—O1	123.3 (4)
N2—C8—H8	109.3	O2—N1—C1	119.1 (5)
C9—C8—H8	109.3	O1—N1—C1	117.6 (4)
C7—C8—H8	109.3	C8—N2—H2B	114.5 (19)
O4—C9—N3	124.7 (2)	C8—N2—H2C	111.6 (18)
O4—C9—C8	119.3 (2)	H2B—N2—H2C	107 (3)
N3—C9—C8	116.0 (2)	C8—N2—H2A	107.1 (19)
O6—C10—O5	124.3 (2)	H2B—N2—H2A	104 (3)
O6—C10—C11	118.5 (2)	H2C—N2—H2A	112 (3)
O5—C10—C11	117.1 (2)	C9—N3—C11	123.3 (2)
N3—C11—C12	109.3 (2)	C9—N3—H3A	118.3
N3—C11—C10	111.00 (19)	C11—N3—H3A	118.3
C12—C11—C10	108.64 (19)	C7—O3—H4	109.5
N3—C11—H11	109.3	H7W—O7—H8W	118.1

C6—C1—C2—C3	0.5 (5)	C7—C8—C9—O4	61.9 (3)
N1—C1—C2—C3	179.3 (3)	N2—C8—C9—N3	122.4 (2)
C1—C2—C3—C4	−0.3 (4)	C7—C8—C9—N3	−116.9 (2)
C2—C3—C4—C5	0.2 (4)	O6—C10—C11—N3	−155.5 (2)
C2—C3—C4—C7	−178.6 (2)	O5—C10—C11—N3	26.6 (3)
C3—C4—C5—C6	−0.2 (4)	O6—C10—C11—C12	84.4 (3)
C7—C4—C5—C6	178.6 (2)	O5—C10—C11—C12	−93.6 (3)
C2—C1—C6—C5	−0.5 (5)	N3—C11—C12—C13	54.7 (3)
N1—C1—C6—C5	−179.3 (3)	C10—C11—C12—C13	175.9 (3)
C4—C5—C6—C1	0.4 (4)	C11—C12—C13—C15	64.0 (4)
C5—C4—C7—O3	119.8 (2)	C11—C12—C13—C14	−172.3 (3)
C3—C4—C7—O3	−61.3 (3)	C2—C1—N1—O2	−174.0 (4)
C5—C4—C7—C8	−120.6 (2)	C6—C1—N1—O2	4.9 (5)
C3—C4—C7—C8	58.2 (3)	C2—C1—N1—O1	4.6 (6)
O3—C7—C8—N2	−47.8 (2)	C6—C1—N1—O1	−176.5 (4)
C4—C7—C8—N2	−170.52 (19)	O4—C9—N3—C11	1.5 (3)
O3—C7—C8—C9	−167.95 (18)	C8—C9—N3—C11	−179.66 (19)
C4—C7—C8—C9	69.4 (2)	C12—C11—N3—C9	−156.1 (2)
N2—C8—C9—O4	−58.8 (3)	C10—C11—N3—C9	84.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7W···O5	0.92	1.87	2.679 (2)	146
O7—H8W···O4ⁱ	0.88	1.96	2.734 (3)	146
N2—H2B···O3ⁱⁱ	0.87 (3)	1.99 (3)	2.854 (3)	172 (3)
O3—H4···O5ⁱⁱⁱ	0.82	1.79	2.612 (2)	175
N3—H3A···O7ⁱ	0.86	2.08	2.914 (3)	163
N2—H2C···O6ⁱ	0.99 (3)	1.96 (3)	2.811 (3)	143 (3)
N2—H2A···O7	0.95 (3)	1.89 (3)	2.801 (2)	158 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x, y−1/2, −z+1; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₁N₃O₆·H₂O
M_r	357.36
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	8.9787 (7), 6.7850 (5), 14.7148 (11)
β (°)	95.362 (5)
V (Å³)	892.51 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.50 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.949, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8245, 2254, 1853
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.105, 1.04
No. of reflections	2254
No. of parameters	243
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: , APEX2 (Bruker, 2005) and SAINT (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7W···O5	0.92	1.87	2.679 (2)	145.7
O7—H8W···O4ⁱ	0.88	1.96	2.734 (3)	145.5
N2—H2B···O3ⁱⁱ	0.87 (3)	1.99 (3)	2.854 (3)	172 (3)
O3—H4···O5ⁱⁱⁱ	0.82	1.79	2.612 (2)	175.2
N3—H3A···O7ⁱ	0.86	2.08	2.914 (3)	162.5
N2—H2C···O6ⁱ	0.99 (3)	1.96 (3)	2.811 (3)	143 (3)
N2—H2A···O7	0.95 (3)	1.89 (3)	2.801 (2)	158 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x, y−1/2, −z+1; (iii) x−1, y, z.

Acknowledgements

Financial support from the National Natural Foundation Research (grant Nos. 30701053, 30772654, 36072541) is gratefully acknowledged.

References

Aozuka, Y., Koizumi, K., Saitoh, Y., Ueda, Y., Sakurai, H. & Saiki, I. (2004). Cancer Lett. 216, 35–42. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shin, W. & Pyo, M. (1984). Bull. Korean Chem. Soc. 5, 158–162. CAS Google Scholar
Shinagawa, S., Kanamaru, T., Harada, S., Asai, M. & Ookazaki, H. (1987). J. Med. Chem. 30, 1458–1463. CrossRef CAS PubMed Web of Science Google Scholar
Testa, M. L., Ciriminna, R., Hajji, C., Garcia, E. Z., Ciclosi, M., Arques, J. S. & Pagliaroa, M. (2004). Adv. Synth. Catal. 346, 655–660. Web of Science CrossRef CAS Google Scholar
Xu, W. F. & Li, Q. B. (2005). Curr. Med. Chem. Anti-Cancer Agents, 5, 281–301. CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2447

doi:10.1107/S1600536808039056

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(S)-2-[(2R,3S)-2-Ammonio-3-hydr­­oxy-3-(4-nitro­phen­yl)propanamido]-4-methyl­penta­noate monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(S)-2-[(2R,3S)-2-Ammonio-3-hydroxy-3-(4-nitrophenyl)propanamido]-4-methylpentanoate monohydrate