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

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ISSN: 2056-9890

Methyl 2-(2-{[(benz­yl­oxy)carbon­yl]amino}­propan-2-yl)-5-hy­dr­oxy-6-meth­­oxy­pyrimidine-4-carboxyl­ate

aCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China
*Correspondence e-mail: zhenhuashang@yahoo.com.cn

(Received 3 April 2011; accepted 29 April 2011; online 7 May 2011)

In the title compound, C18H21N3O6, the dihedral angle between the two aromatic rings is 61.1 (1)°. The crystal structure is stabilized by inter­molecular O—H⋯O hydrogen bonds. An intra­molecular O—H⋯O hydrogen bonds is also present.

Related literature

The title compound was obtained in an attempt to synthesise an inter­mediate for the anti­retroviral drug raltegravir [sys­tem­atic name N-(2-(4-(4-fluoro­benzyl­carbamo­yl)-5-hy­droxy-1-methyl-6-oxo-1,6-dihydro­pyrimidin-2-yl)propan-2-yl)-5-methyl-1,3,4-oxadiazole-2-carboxamide], see: Belyk et al. (2006)[Belyk, M., Morrison, G. & Jones, P. (2006). Patent No. WO200606712. ]. For background to raltegravir, see: Steigbigel et al. (2008[Steigbigel, et al. (2008). N. Engl. J. Med. 359, 339-354.]). For related structures, see: Shang & Shang (2007[Shang, Z.-H. & Shang, Q. (2007). Acta Cryst. E63, o2280-o2281.]); Fun et al. (2009[Fun, H.-K., Balasubramani, K., Hazra, A., Kumar Das, M. & Goswami, S. (2009). Acta Cryst. E65, o1484-o1485.]).

[Scheme 1]

Experimental

Crystal data
  • C18H21N3O6

  • Mr = 375.38

  • Monoclinic, P 21

  • a = 8.5313 (17) Å

  • b = 6.5413 (13) Å

  • c = 16.167 (3) Å

  • β = 97.37 (3)°

  • V = 894.7 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 113 K

  • 0.20 × 0.16 × 0.12 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.987

  • 7509 measured reflections

  • 2281 independent reflections

  • 1854 reflections with I > 2σ(I)

  • Rint = 0.044

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.088

  • S = 1.01

  • 2281 reflections

  • 256 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O5i 0.87 (3) 2.27 (3) 2.889 (2) 128 (2)
O2—H2⋯O3 0.87 (3) 1.95 (3) 2.652 (2) 136 (3)
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+2].

Data collection: SMART (Bruker, 1997[Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Raltegravir (MK-0518, brand name Isentress) is an antiretroviral drug produced by Merck & Co, used to treat HIV infection (Steigbigel et al., 2008). It received FDA approval in October 2007, the first of a new class of HIV drugs, the integrase inhibitors, to receive such approval. When methyl 2-(2-(benzyloxycarbonyl)propan-2-yl) -5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate was reacted with dimethyl sulfate catalyzed by magnesium methoxide in dimethyl sulfoxide (Belyk et al., 2006), as we designed, in order to synthesize methyl 2-(2-(benzyloxycarbonyl)propan-2-yl) -5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate as the key intermediate of Raltegravir, two products appeared on thin layer chromatography. These products were separated through flash chromatography and the structures were conformed by nuclear magnetic resonance and X-ray analysis. The result showed that the title compound was the byproduct of the reaction. The pyrimidinone ring is planar, as it is in a related compound (Fun et al., 2009). This is in contrast with another related compound (Shang et al., 2007), where the heterocyclic ring is twisted. In the title compound the dihedral angle between the two aromatic rings is 118.9 (1)°. The crystal structure is stabilized through intermolecular O—H···O hydrogen bonds; intramolecular O—H···O hydrogen bonds are also present.

Related literature top

The title compound was obtained in an attempt to synthesise an intermediate for the the antiretroviral drug raltegravir [systematic name N-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)-5-methyl-1,3,4-oxadiazole-2-carboxamide], see: Belyk et al. (2006). For background to raltegravir, see: Steigbigel et al. (2008). For related structures, see: Shang & Shang (2007); Fun et al. (2009).

Experimental top

To a slurry of methyl 2-(2-(benzyloxycarbonyl)propan-2-yl) -5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (1.5 g) and magnesium methoxide (2.1 g) in dimethyl sulfoxide(15 ml) at 70 °C, dimethyl sulfate (3.1 g) was added dropwise. After addition, the mixture was heated at the same temperature for 8 h. To the reaction mixture was then added 40 ml 2 N HCl and then 100 ml water. Solid appeared when the mixture was stirred in an ice-water bath. The products were filtered and separated by flash chromatography. 50 mg of the title compound was dissolved in 30 ml methanol and the solution was kept at room temperature for 10 d; natural evaporation gave colorless single crystals of the title compound suitable for X-ray analysis.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.95 Å(aromatic), 0.98 Å(methyl group) or 0.99 Å(methylene group). Uiso(H) = xUeq(C). where x = 1.5 for methyl H and 1.2 for all other carbon-bound H atoms. The positional parameters of the oxygen-bound H atoms and nitrogen-bound H atoms were refined freely(O-H=0.87 (3)Å, N-H=0.92 (3)Å).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, drawn with 30% probability ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
Methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)- 5-hydroxy-6-methoxypyrimidine-4-carboxylate top
Crystal data top
C18H21N3O6F(000) = 396
Mr = 375.38Dx = 1.393 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3543 reflections
a = 8.5313 (17) Åθ = 2.3–27.5°
b = 6.5413 (13) ŵ = 0.11 mm1
c = 16.167 (3) ÅT = 113 K
β = 97.37 (3)°Plate, colorless
V = 894.7 (3) Å30.20 × 0.16 × 0.12 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
2281 independent reflections
Radiation source: rotating anode1854 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.044
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.5°
ω and ϕ scansh = 1011
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
k = 78
Tmin = 0.979, Tmax = 0.987l = 2120
7509 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0491P)2]
where P = (Fo2 + 2Fc2)/3
2281 reflections(Δ/σ)max = 0.001
256 parametersΔρmax = 0.25 e Å3
1 restraintΔρmin = 0.21 e Å3
Crystal data top
C18H21N3O6V = 894.7 (3) Å3
Mr = 375.38Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.5313 (17) ŵ = 0.11 mm1
b = 6.5413 (13) ÅT = 113 K
c = 16.167 (3) Å0.20 × 0.16 × 0.12 mm
β = 97.37 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2281 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
1854 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.987Rint = 0.044
7509 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0391 restraint
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.25 e Å3
2281 reflectionsΔρmin = 0.21 e Å3
256 parameters
Special details top

Experimental. 1H-NMR (500 MHz, CDCl3) 1.72(s, 6H), 3.66(s, 3H), 3.97(s, 3H), 5.03(s, 2H), 5.28 (s, 1H), 7.02–7.32(m, 5H, J=75 Hz), 10.39(s, 1H).

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
xyzUiso*/Ueq
N10.7129 (2)0.6028 (3)0.89047 (10)0.0184 (4)
N20.4395 (2)0.6250 (3)0.83861 (10)0.0192 (4)
N30.4877 (2)0.4973 (3)0.68708 (11)0.0210 (4)
H30.427 (3)0.599 (5)0.6595 (17)0.043 (8)*
O10.25348 (16)0.6638 (3)0.92818 (9)0.0220 (4)
O20.46916 (18)0.6583 (3)1.06058 (9)0.0219 (4)
H20.547 (3)0.670 (6)1.1011 (18)0.050 (9)*
O30.77719 (17)0.6582 (3)1.11167 (8)0.0244 (4)
O40.94697 (16)0.6036 (3)1.01878 (9)0.0231 (4)
O50.4667 (2)0.2009 (2)0.76039 (9)0.0259 (4)
O60.26425 (19)0.3210 (3)0.66809 (10)0.0287 (4)
C10.5941 (2)0.6005 (3)0.82953 (12)0.0185 (5)
C20.4043 (2)0.6444 (3)0.91420 (12)0.0183 (4)
C30.5207 (2)0.6435 (3)0.98553 (12)0.0174 (4)
C40.6744 (2)0.6263 (3)0.96913 (12)0.0174 (4)
C50.1359 (2)0.6528 (4)0.85502 (12)0.0240 (5)
H5A0.14370.77460.82050.036*
H5B0.03020.64600.87250.036*
H5C0.15440.53040.82270.036*
C60.8042 (2)0.6304 (4)1.04017 (12)0.0193 (4)
C71.0779 (3)0.6187 (4)1.08615 (13)0.0258 (5)
H7A1.09330.76201.10290.039*
H7B1.17450.56631.06690.039*
H7C1.05370.53791.13400.039*
C80.6296 (3)0.5754 (3)0.73967 (13)0.0197 (5)
C90.7695 (3)0.4322 (4)0.73342 (14)0.0261 (6)
H9A0.74350.29470.75150.039*
H9B0.86270.48310.76930.039*
H9C0.79200.42710.67550.039*
C100.6641 (3)0.7866 (4)0.70588 (15)0.0285 (6)
H10A0.67960.77500.64700.043*
H10B0.76000.84220.73780.043*
H10C0.57490.87800.71110.043*
C110.4121 (3)0.3289 (4)0.71076 (12)0.0211 (5)
C120.1749 (3)0.1388 (4)0.67933 (14)0.0313 (6)
H12A0.06160.17460.67620.038*
H12B0.20920.08200.73550.038*
C130.1953 (3)0.0221 (4)0.61451 (14)0.0248 (5)
C140.3061 (3)0.0041 (5)0.55949 (14)0.0322 (6)
H140.37420.11120.56250.039*
C150.3181 (3)0.1545 (5)0.49977 (15)0.0399 (7)
H150.39420.14110.46210.048*
C160.2197 (4)0.3238 (5)0.49494 (16)0.0427 (7)
H160.22900.42680.45440.051*
C170.1087 (3)0.3423 (5)0.54905 (15)0.0379 (7)
H170.04010.45720.54550.046*
C180.0970 (3)0.1928 (4)0.60889 (14)0.0293 (6)
H180.02090.20720.64650.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0175 (9)0.0203 (10)0.0177 (8)0.0002 (8)0.0028 (7)0.0018 (7)
N20.0165 (9)0.0218 (9)0.0190 (8)0.0010 (8)0.0020 (7)0.0023 (8)
N30.0206 (10)0.0237 (10)0.0178 (9)0.0015 (8)0.0011 (7)0.0003 (8)
O10.0129 (8)0.0321 (9)0.0211 (7)0.0017 (7)0.0021 (6)0.0023 (7)
O20.0196 (8)0.0282 (9)0.0176 (7)0.0007 (7)0.0020 (6)0.0022 (7)
O30.0215 (8)0.0348 (10)0.0170 (7)0.0017 (8)0.0035 (6)0.0023 (7)
O40.0126 (8)0.0357 (10)0.0209 (7)0.0004 (7)0.0014 (6)0.0023 (7)
O50.0303 (10)0.0250 (9)0.0225 (8)0.0032 (7)0.0037 (7)0.0021 (7)
O60.0249 (9)0.0295 (9)0.0295 (8)0.0040 (8)0.0044 (7)0.0018 (7)
C10.0180 (11)0.0182 (11)0.0193 (10)0.0003 (9)0.0024 (8)0.0012 (8)
C20.0161 (11)0.0153 (11)0.0236 (10)0.0004 (9)0.0032 (8)0.0011 (9)
C30.0208 (11)0.0141 (10)0.0174 (9)0.0015 (9)0.0026 (8)0.0019 (8)
C40.0174 (11)0.0164 (10)0.0182 (9)0.0007 (9)0.0017 (8)0.0012 (8)
C50.0176 (11)0.0316 (13)0.0214 (11)0.0008 (10)0.0028 (8)0.0020 (10)
C60.0200 (11)0.0191 (11)0.0184 (10)0.0026 (10)0.0009 (8)0.0002 (9)
C70.0190 (12)0.0376 (14)0.0196 (10)0.0044 (11)0.0016 (9)0.0005 (10)
C80.0168 (11)0.0253 (12)0.0169 (10)0.0001 (9)0.0010 (8)0.0015 (8)
C90.0196 (13)0.0385 (14)0.0199 (11)0.0036 (10)0.0012 (9)0.0043 (10)
C100.0291 (14)0.0307 (13)0.0266 (12)0.0061 (11)0.0073 (10)0.0002 (10)
C110.0222 (12)0.0257 (12)0.0157 (10)0.0002 (10)0.0037 (9)0.0054 (9)
C120.0270 (13)0.0359 (15)0.0317 (12)0.0110 (12)0.0068 (10)0.0065 (12)
C130.0214 (12)0.0316 (13)0.0204 (10)0.0016 (10)0.0009 (9)0.0004 (9)
C140.0267 (14)0.0426 (16)0.0269 (12)0.0030 (12)0.0021 (10)0.0024 (11)
C150.0376 (16)0.056 (2)0.0256 (12)0.0101 (15)0.0042 (11)0.0030 (13)
C160.0589 (19)0.0398 (17)0.0267 (13)0.0142 (15)0.0054 (13)0.0064 (12)
C170.0522 (17)0.0255 (13)0.0324 (13)0.0012 (13)0.0088 (12)0.0023 (11)
C180.0325 (14)0.0309 (14)0.0231 (11)0.0050 (11)0.0020 (10)0.0032 (10)
Geometric parameters (Å, º) top
N1—C11.320 (2)C7—H7B0.9800
N1—C41.363 (3)C7—H7C0.9800
N2—C21.301 (3)C8—C101.528 (3)
N2—C11.355 (3)C8—C91.531 (3)
N3—C111.357 (3)C9—H9A0.9800
N3—C81.478 (3)C9—H9B0.9800
N3—H30.92 (3)C9—H9C0.9800
O1—C21.341 (2)C10—H10A0.9800
O1—C51.451 (2)C10—H10B0.9800
O2—C31.346 (3)C10—H10C0.9800
O2—H20.87 (3)C12—C131.511 (3)
O3—C61.221 (2)C12—H12A0.9900
O4—C61.320 (3)C12—H12B0.9900
O4—C71.460 (2)C13—C141.384 (3)
O5—C111.211 (3)C13—C181.392 (4)
O6—C111.358 (3)C14—C151.391 (4)
O6—C121.438 (3)C14—H140.9500
C1—C81.530 (3)C15—C161.386 (5)
C2—C31.422 (3)C15—H150.9500
C3—C41.375 (3)C16—C171.375 (4)
C4—C61.490 (3)C16—H160.9500
C5—H5A0.9800C17—C181.388 (4)
C5—H5B0.9800C17—H170.9500
C5—H5C0.9800C18—H180.9500
C7—H7A0.9800
C1—N1—C4116.32 (18)C1—C8—C9112.28 (18)
C2—N2—C1117.25 (17)C8—C9—H9A109.5
C11—N3—C8120.17 (17)C8—C9—H9B109.5
C11—N3—H3117.4 (18)H9A—C9—H9B109.5
C8—N3—H3113.6 (19)C8—C9—H9C109.5
C2—O1—C5115.85 (16)H9A—C9—H9C109.5
C3—O2—H2112 (2)H9B—C9—H9C109.5
C6—O4—C7116.03 (16)C8—C10—H10A109.5
C11—O6—C12116.08 (19)C8—C10—H10B109.5
N1—C1—N2125.66 (19)H10A—C10—H10B109.5
N1—C1—C8118.88 (18)C8—C10—H10C109.5
N2—C1—C8115.42 (17)H10A—C10—H10C109.5
N2—C2—O1120.61 (17)H10B—C10—H10C109.5
N2—C2—C3122.69 (19)O5—C11—N3126.3 (2)
O1—C2—C3116.69 (18)O5—C11—O6124.3 (2)
O2—C3—C4127.57 (18)N3—C11—O6109.39 (18)
O2—C3—C2117.10 (18)O6—C12—C13112.31 (19)
C4—C3—C2115.33 (18)O6—C12—H12A109.1
N1—C4—C3122.66 (17)C13—C12—H12A109.1
N1—C4—C6118.47 (18)O6—C12—H12B109.1
C3—C4—C6118.86 (18)C13—C12—H12B109.1
O1—C5—H5A109.5H12A—C12—H12B107.9
O1—C5—H5B109.5C14—C13—C18118.8 (2)
H5A—C5—H5B109.5C14—C13—C12122.4 (2)
O1—C5—H5C109.5C18—C13—C12118.8 (2)
H5A—C5—H5C109.5C13—C14—C15120.2 (3)
H5B—C5—H5C109.5C13—C14—H14119.9
O3—C6—O4124.10 (18)C15—C14—H14119.9
O3—C6—C4121.35 (19)C16—C15—C14120.4 (3)
O4—C6—C4114.55 (17)C16—C15—H15119.8
O4—C7—H7A109.5C14—C15—H15119.8
O4—C7—H7B109.5C17—C16—C15119.7 (3)
H7A—C7—H7B109.5C17—C16—H16120.1
O4—C7—H7C109.5C15—C16—H16120.1
H7A—C7—H7C109.5C16—C17—C18119.9 (3)
H7B—C7—H7C109.5C16—C17—H17120.0
N3—C8—C10106.74 (17)C18—C17—H17120.0
N3—C8—C1109.65 (18)C17—C18—C13120.9 (3)
C10—C8—C1108.25 (18)C17—C18—H18119.5
N3—C8—C9109.79 (19)C13—C18—H18119.5
C10—C8—C9110.0 (2)
C4—N1—C1—N22.0 (3)C11—N3—C8—C10168.3 (2)
C4—N1—C1—C8179.8 (2)C11—N3—C8—C151.3 (3)
C2—N2—C1—N12.9 (3)C11—N3—C8—C972.5 (3)
C2—N2—C1—C8179.2 (2)N1—C1—C8—N3158.04 (19)
C1—N2—C2—O1178.2 (2)N2—C1—C8—N323.9 (3)
C1—N2—C2—C30.9 (3)N1—C1—C8—C1085.9 (2)
C5—O1—C2—N22.5 (3)N2—C1—C8—C1092.1 (2)
C5—O1—C2—C3176.63 (19)N1—C1—C8—C935.7 (3)
N2—C2—C3—O2177.9 (2)N2—C1—C8—C9146.3 (2)
O1—C2—C3—O21.2 (3)C8—N3—C11—O519.5 (3)
N2—C2—C3—C41.7 (3)C8—N3—C11—O6162.23 (18)
O1—C2—C3—C4179.13 (19)C12—O6—C11—O55.0 (3)
C1—N1—C4—C31.0 (3)C12—O6—C11—N3173.27 (18)
C1—N1—C4—C6179.9 (2)C11—O6—C12—C1392.1 (2)
O2—C3—C4—N1176.9 (2)O6—C12—C13—C149.1 (3)
C2—C3—C4—N12.7 (3)O6—C12—C13—C18169.70 (19)
O2—C3—C4—C62.2 (3)C18—C13—C14—C150.1 (3)
C2—C3—C4—C6178.2 (2)C12—C13—C14—C15178.7 (2)
C7—O4—C6—O32.9 (3)C13—C14—C15—C160.2 (4)
C7—O4—C6—C4176.54 (19)C14—C15—C16—C170.6 (4)
N1—C4—C6—O3177.4 (2)C15—C16—C17—C180.8 (4)
C3—C4—C6—O33.5 (3)C16—C17—C18—C130.7 (4)
N1—C4—C6—O42.1 (3)C14—C13—C18—C170.4 (3)
C3—C4—C6—O4177.1 (2)C12—C13—C18—C17178.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O5i0.87 (3)2.27 (3)2.889 (2)128 (2)
O2—H2···O30.87 (3)1.95 (3)2.652 (2)136 (3)
Symmetry code: (i) x+1, y+1/2, z+2.

Experimental details

Crystal data
Chemical formulaC18H21N3O6
Mr375.38
Crystal system, space groupMonoclinic, P21
Temperature (K)113
a, b, c (Å)8.5313 (17), 6.5413 (13), 16.167 (3)
β (°) 97.37 (3)
V3)894.7 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.20 × 0.16 × 0.12
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.979, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
7509, 2281, 1854
Rint0.044
(sin θ/λ)max1)0.657
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.088, 1.01
No. of reflections2281
No. of parameters256
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O5i0.87 (3)2.27 (3)2.889 (2)128 (2)
O2—H2···O30.87 (3)1.95 (3)2.652 (2)136 (3)
Symmetry code: (i) x+1, y+1/2, z+2.
 

Acknowledgements

The authors thank the funds of Hebei Province Science and Technology Research and Development Projects (No. 08276409D) and Hebei University of Science and Technology.

References

First citationBelyk, M., Morrison, G. & Jones, P. (2006). Patent No. WO200606712.  Google Scholar
First citationBruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFun, H.-K., Balasubramani, K., Hazra, A., Kumar Das, M. & Goswami, S. (2009). Acta Cryst. E65, o1484–o1485.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationShang, Z.-H. & Shang, Q. (2007). Acta Cryst. E63, o2280–o2281.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSteigbigel, et al. (2008). N. Engl. J. Med. 359, 339–354.  Web of Science CrossRef PubMed Google Scholar

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