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organic compounds
(S)-2-[(2R,3S)-2-Ammonio-3-hydroxy-3-(4-nitrophenyl)propanamido]-4-methylpentanoate monohydrate
aInstitute of Medicinal Chemistry, School of Pharmacy, Shandong University, Ji'nan 250012, People's Republic of China
*Correspondence e-mail: xuwenfsdu@yahoo.cn
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
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2005); cell 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
10.1107/S1600536808039056/si2128sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808039056/si2128Isup2.hkl
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.
All H atoms were positioned geometrically using a riding model with C—H = 0.92–1.02 Å, N—H = 0.86 and O—H = 0.82 Å. Their isotropic displacement parameters were set to 1.2 times (1.5 times for CH3 groups) the equivalent displacement parameter of their parent atoms. In addition, the three H atoms at N2 were located from a difference Fourier map and refined isotropically, with N–H distances in the range 0.88 (3)–0.92 (3) Å with Uiso(H) = 1.3–1.75 times Ueq(N2).
In the absence of significant
effects, 1625 Friedel pairs were averaged.Data collection: APEX2 (Bruker, 2005); cell
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).C15H21N3O6·H2O | F(000) = 380 |
Mr = 357.36 | Dx = 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 |
Bruker APEXII CCD area-detector diffractometer | 2254 independent reflections |
Radiation source: fine-focus sealed tube | 1853 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ϕ and ω scans | θmax = 27.6°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −11→11 |
Tmin = 0.949, Tmax = 0.984 | k = −8→8 |
8245 measured reflections | l = −19→18 |
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(Fo2) + (0.059P)2 + 0.0778P] where P = (Fo2 + 2Fc2)/3 |
2254 reflections | (Δ/σ)max < 0.001 |
243 parameters | Δρmax = 0.19 e Å−3 |
1 restraint | Δρmin = −0.16 e Å−3 |
C15H21N3O6·H2O | V = 892.51 (12) Å3 |
Mr = 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)° |
Bruker APEXII CCD area-detector diffractometer | 2254 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1853 reflections with I > 2σ(I) |
Tmin = 0.949, Tmax = 0.984 | Rint = 0.028 |
8245 measured reflections |
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 | Δρmax = 0.19 e Å−3 |
2254 reflections | Δρmin = −0.16 e Å−3 |
243 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.949, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8245, 2254, 1853 |
Rint | 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 |
Δρmax, Δρmin (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).
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
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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.