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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1150

5-tert-Butyl 1-ethyl 3-amino-1,4,5,6-tetra­hydro­pyrrolo­[3,4-c]pyrazole-1,5-di­carboxyl­ate

aSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China, and bInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050, People's Republic of China
*Correspondence e-mail: imbjxwang@gmail.com

(Received 29 March 2011; accepted 11 April 2011; online 16 April 2011)

The asymmetric unit of the title compound, C13H20N4O4, contains two crystallographically independent mol­ecules in which the dihedral angles between the fused pyrrole and pyrazole rings are 5.06 (8) and 1.12 (8)°. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O and N—H⋯N hydrogen bonds into chains parallel to the b axis.

Related literature

For general background to potential anti­cancer kinase inhibitors, see: Fancelli et al. (2005[Fancelli, D., et al. (2005). J. Med. Chem. 48, 3080-3084.]); Gadekar et al. (1968[Gadekar, S. M., Johnson, B. D. & Cohen, E. (1968). J. Med. Chem. 11, 616-618.]). For the structure of a related compound synthesized by our group, see: Guo et al. (2010[Guo, X., Bai, X. G., Li, Y. L. & Wang, Y. C. (2010). Acta Cryst. E66, o1108.]).

[Scheme 1]

Experimental

Crystal data
  • C13H20N4O4

  • Mr = 296.33

  • Triclinic, [P \overline 1]

  • a = 10.772 (3) Å

  • b = 12.180 (4) Å

  • c = 12.986 (4) Å

  • α = 70.845 (5)°

  • β = 65.875 (4)°

  • γ = 85.821 (5)°

  • V = 1465.2 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.06 × 0.05 × 0.04 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.994, Tmax = 0.996

  • 7444 measured reflections

  • 5102 independent reflections

  • 3915 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.128

  • S = 1.03

  • 5102 reflections

  • 387 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N8—H8"⋯O4i 0.86 2.25 3.069 (3) 160
N8—H8′⋯N2ii 0.86 2.26 3.087 (3) 163
N4—H4′⋯N6iii 0.90 2.25 3.104 (3) 157
N4—H4"⋯O8iv 0.90 2.36 3.233 (3) 163
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x-1, y-1, z; (iv) x-1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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

As an extension of our work (Guo et al., 2010) on the development of potential anticancer kinase inhibitors (Fancelli et al., 2005; Gadekar et al., 1968), we have synthesized the title compound and report its crystal structure herein.

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules. All bond lengths and angles have normal values. The dihedral angles between the fused pyrrole and pyrazole rings are 5.06 (8) and 1.12 (8)°. The C6/O1/O2/C7 and C9/O4/O3/C10 mean planes form dihedral angles of 5.83(0.09)° and 14.86(0.10) °, respectively, with the mean plane through N1/N2/C2/C1/C3/C4/C5/N3, whereas the O8/C22/O7/C23 and C18/O5/O6/C17 mean planes form dihedral angles of 6.20(0.12) ° and 5.12(0.13) °, respectively, with the N5/N6/C14/C15/C16/C20/C21/N7 mean plane. In the crystal structure (Fig.2), molecules are linked by intermolecular N—H···O and N—H···N hydrogen bonds (Table 1) to form chains running parallel to the b axis.

Related literature top

For general background to potential anticancer kinase inhibitors, see: Fancelli et al. (2005); Gadekar et al. (1968). For the structure of a related compound synthesized by our group, see: Guo et al. (2010).

Experimental top

A solution of ethyl chlorocarbonate (2.90 g, 12 mmol) in THF (30 ml) was slowly added dropwise to a mixture of tert-butyl 3-aminopyrrolo[3,4-c]pyrazole-5(1H,4H,6H)-carboxylate (3.3 g, 11 mmol) and DIEA (8.54 g, 66 mmol) in THF (60 ml) at 0~5 °C. The reaction was kept at the same temperature for 2 h, allowed to reach r.t., and stirred overnight. The obtained mixture was evaporated to dryness and the resulting residue extracted with AcOEt and water. The organic layer was separated, dried over sodium sulfate, and evaporated to dryness. The residue was purified by flash chromatography to give 1.8 g (55%) of the title compound as a white solid. Colourless block crystals suitable for X-ray diffraction were obtained in 2 days by slow evaporation of a methanol solution.

Refinement top

The hydrogen atoms could have been discerned in the difference Fourier map, nevertheless all H atoms were placed at calculated positions and refined as riding, with C—H = 0.96-0.97 Å, N—H = 0.86-0.90 Å, and with Uiso(H) = 1.2 Ueq(C, N) or 1.5 Ueq(C) for methyl H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed along the c axis. Hydrogen bonds are shown as dashed lines.
5-tert-Butyl 1-ethyl 3-amino-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate top
Crystal data top
C13H20N4O4Z = 4
Mr = 296.33F(000) = 632
Triclinic, P1Dx = 1.343 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.772 (3) ÅCell parameters from 2737 reflections
b = 12.180 (4) Åθ = 2.6–28.0°
c = 12.986 (4) ŵ = 0.10 mm1
α = 70.845 (5)°T = 296 K
β = 65.875 (4)°Block, colourless
γ = 85.821 (5)°0.06 × 0.05 × 0.04 mm
V = 1465.2 (7) Å3
Data collection top
Bruker APEXII CCD
diffractometer
5102 independent reflections
Radiation source: fine-focus sealed tube3915 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1210
Tmin = 0.994, Tmax = 0.996k = 1214
7444 measured reflectionsl = 1510
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0632P)2 + 0.4323P]
where P = (Fo2 + 2Fc2)/3
5102 reflections(Δ/σ)max < 0.001
387 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C13H20N4O4γ = 85.821 (5)°
Mr = 296.33V = 1465.2 (7) Å3
Triclinic, P1Z = 4
a = 10.772 (3) ÅMo Kα radiation
b = 12.180 (4) ŵ = 0.10 mm1
c = 12.986 (4) ÅT = 296 K
α = 70.845 (5)°0.06 × 0.05 × 0.04 mm
β = 65.875 (4)°
Data collection top
Bruker APEXII CCD
diffractometer
5102 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
3915 reflections with I > 2σ(I)
Tmin = 0.994, Tmax = 0.996Rint = 0.026
7444 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.03Δρmax = 0.26 e Å3
5102 reflectionsΔρmin = 0.32 e Å3
387 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
xyzUiso*/Ueq
O10.26829 (15)0.40073 (13)0.06447 (14)0.0348 (4)
O20.15420 (17)0.22918 (13)0.11483 (14)0.0383 (4)
O30.18836 (13)0.80172 (12)0.11637 (12)0.0248 (3)
O40.02679 (14)0.86224 (13)0.15737 (14)0.0303 (4)
O50.28280 (14)1.06702 (13)0.45631 (14)0.0333 (4)
O60.39625 (15)1.23659 (13)0.41233 (14)0.0348 (4)
O70.33735 (13)0.66947 (12)0.40945 (12)0.0263 (3)
O80.54850 (14)0.63169 (12)0.29063 (12)0.0264 (3)
N10.04383 (17)0.39313 (15)0.13325 (15)0.0266 (4)
N20.08554 (17)0.34058 (15)0.17464 (16)0.0278 (4)
N30.03062 (16)0.69338 (14)0.12056 (15)0.0252 (4)
N40.30512 (18)0.40713 (16)0.22648 (17)0.0334 (5)
H4"0.36270.46070.24820.050*
H4'0.34380.33390.26410.050*
N50.50579 (16)1.08232 (14)0.36264 (15)0.0240 (4)
N60.63493 (17)1.14050 (15)0.30111 (15)0.0259 (4)
N70.51226 (16)0.79033 (14)0.34994 (15)0.0238 (4)
N80.85181 (18)1.08823 (16)0.19749 (17)0.0363 (5)
H8'0.88731.15590.18180.044*
H8"0.90261.03660.17260.044*
C10.0358 (2)0.50843 (17)0.12258 (17)0.0240 (5)
C20.1695 (2)0.42522 (18)0.18909 (18)0.0265 (5)
C30.0945 (2)0.53222 (18)0.15632 (18)0.0239 (5)
C40.1110 (2)0.65547 (17)0.15288 (19)0.0252 (5)
H4D0.14350.69980.09290.030*
H4E0.17210.66110.23000.030*
C50.1312 (2)0.60819 (17)0.08967 (18)0.0247 (5)
H5A0.18480.59070.13690.030*
H5B0.19140.63370.00540.030*
C60.1580 (2)0.33069 (19)0.10486 (18)0.0289 (5)
C70.3986 (2)0.3522 (2)0.0194 (2)0.0403 (6)
H7A0.46670.41440.03990.048*
H7B0.39170.29830.01910.048*
C80.4422 (3)0.2901 (3)0.1178 (2)0.0500 (7)
H8D0.43880.34080.16190.075*
H8E0.53370.26790.08450.075*
H8F0.38220.22180.17030.075*
C90.0578 (2)0.79265 (17)0.13261 (18)0.0233 (5)
C100.24457 (19)0.90541 (17)0.12164 (18)0.0230 (5)
C110.3866 (2)0.87316 (18)0.10925 (19)0.0286 (5)
H11A0.38150.80110.17070.043*
H11B0.43150.93350.11680.043*
H11C0.43710.86430.03240.043*
C120.1652 (2)0.9233 (2)0.24050 (18)0.0303 (5)
H12A0.07560.94550.24680.046*
H12B0.21160.98370.24660.046*
H12C0.15770.85220.30380.046*
C130.2481 (2)1.00881 (18)0.01703 (18)0.0279 (5)
H13A0.29990.99270.05590.042*
H13B0.28991.07600.01660.042*
H13C0.15671.02350.02390.042*
C140.7175 (2)1.06333 (17)0.26074 (18)0.0242 (5)
C150.6416 (2)0.95619 (17)0.29503 (17)0.0223 (4)
C160.5126 (2)0.97181 (17)0.35743 (17)0.0226 (4)
C170.3930 (2)1.13870 (19)0.41168 (18)0.0272 (5)
C180.1527 (2)1.1110 (2)0.5106 (2)0.0393 (6)
H18A0.16241.16300.55000.047*
H18B0.08801.04670.57040.047*
C190.0999 (3)1.1747 (3)0.4194 (2)0.0500 (7)
H19A0.15631.24520.36750.075*
H19B0.00801.19350.45850.075*
H19C0.10141.12660.37340.075*
C200.4166 (2)0.86791 (17)0.40609 (18)0.0245 (5)
H20A0.37990.83690.49260.029*
H20B0.34260.88390.38020.029*
C210.65594 (19)0.83642 (17)0.28762 (18)0.0227 (4)
H21A0.69510.83740.20550.027*
H21B0.71080.79220.32830.027*
C220.4724 (2)0.69102 (17)0.34557 (17)0.0223 (4)
C230.2682 (2)0.55632 (18)0.43977 (19)0.0269 (5)
C240.3325 (2)0.45964 (18)0.5035 (2)0.0318 (5)
H24A0.42430.45470.44990.048*
H24B0.28090.38720.53030.048*
H24C0.33350.47530.57100.048*
C250.2688 (2)0.5414 (2)0.3285 (2)0.0366 (6)
H25A0.23130.60730.28910.055*
H25B0.21480.47170.35000.055*
H25C0.36070.53580.27560.055*
C260.1261 (2)0.5688 (2)0.5249 (2)0.0355 (6)
H26A0.13100.59110.58760.053*
H26B0.07320.49580.55880.053*
H26C0.08370.62740.48250.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0307 (8)0.0283 (9)0.0448 (9)0.0079 (7)0.0123 (7)0.0166 (7)
O20.0497 (10)0.0235 (9)0.0474 (10)0.0099 (7)0.0223 (8)0.0171 (7)
O30.0228 (7)0.0174 (7)0.0364 (8)0.0017 (6)0.0129 (6)0.0105 (6)
O40.0246 (8)0.0212 (8)0.0471 (9)0.0035 (6)0.0139 (7)0.0151 (7)
O50.0252 (8)0.0301 (9)0.0415 (9)0.0043 (7)0.0074 (7)0.0165 (7)
O60.0394 (9)0.0243 (9)0.0429 (9)0.0074 (7)0.0140 (7)0.0184 (7)
O70.0257 (8)0.0195 (8)0.0348 (8)0.0016 (6)0.0130 (6)0.0089 (6)
O80.0308 (8)0.0185 (8)0.0308 (8)0.0028 (6)0.0126 (6)0.0094 (6)
N10.0303 (9)0.0179 (9)0.0328 (10)0.0031 (7)0.0125 (8)0.0106 (8)
N20.0319 (10)0.0197 (9)0.0331 (10)0.0011 (8)0.0137 (8)0.0096 (8)
N30.0234 (9)0.0187 (9)0.0354 (10)0.0032 (7)0.0120 (8)0.0115 (8)
N40.0298 (10)0.0221 (10)0.0455 (11)0.0031 (8)0.0124 (9)0.0103 (9)
N50.0252 (9)0.0170 (9)0.0291 (9)0.0010 (7)0.0101 (7)0.0081 (7)
N60.0258 (9)0.0191 (9)0.0313 (10)0.0001 (7)0.0100 (8)0.0083 (8)
N70.0241 (9)0.0186 (9)0.0309 (9)0.0018 (7)0.0117 (7)0.0103 (7)
N80.0266 (10)0.0200 (10)0.0557 (13)0.0013 (8)0.0077 (9)0.0156 (9)
C10.0319 (11)0.0191 (11)0.0244 (10)0.0021 (9)0.0134 (9)0.0088 (9)
C20.0340 (12)0.0213 (11)0.0256 (11)0.0009 (9)0.0134 (9)0.0070 (9)
C30.0274 (11)0.0205 (11)0.0269 (11)0.0030 (9)0.0128 (9)0.0096 (9)
C40.0264 (11)0.0188 (11)0.0325 (11)0.0003 (8)0.0133 (9)0.0090 (9)
C50.0267 (11)0.0209 (11)0.0290 (11)0.0040 (9)0.0116 (9)0.0113 (9)
C60.0391 (13)0.0229 (12)0.0278 (11)0.0068 (10)0.0148 (10)0.0116 (9)
C70.0344 (13)0.0409 (15)0.0446 (14)0.0137 (11)0.0116 (11)0.0210 (12)
C80.0479 (15)0.0555 (18)0.0545 (17)0.0147 (13)0.0253 (13)0.0244 (14)
C90.0248 (10)0.0175 (10)0.0254 (10)0.0007 (9)0.0097 (9)0.0047 (8)
C100.0221 (10)0.0180 (10)0.0280 (11)0.0034 (8)0.0092 (8)0.0068 (8)
C110.0268 (11)0.0234 (11)0.0346 (12)0.0006 (9)0.0130 (9)0.0077 (9)
C120.0285 (11)0.0338 (13)0.0294 (11)0.0005 (9)0.0108 (9)0.0118 (10)
C130.0295 (11)0.0211 (11)0.0305 (11)0.0025 (9)0.0107 (9)0.0074 (9)
C140.0284 (11)0.0176 (11)0.0270 (11)0.0006 (9)0.0122 (9)0.0064 (9)
C150.0257 (11)0.0175 (10)0.0236 (10)0.0007 (8)0.0108 (9)0.0055 (8)
C160.0284 (11)0.0180 (10)0.0237 (10)0.0017 (8)0.0131 (9)0.0064 (8)
C170.0314 (12)0.0255 (12)0.0273 (11)0.0054 (9)0.0125 (9)0.0119 (9)
C180.0292 (12)0.0452 (15)0.0402 (13)0.0077 (11)0.0044 (10)0.0234 (12)
C190.0383 (14)0.0593 (18)0.0593 (17)0.0192 (13)0.0192 (13)0.0320 (15)
C200.0247 (10)0.0210 (11)0.0285 (11)0.0015 (8)0.0103 (9)0.0096 (9)
C210.0246 (10)0.0169 (10)0.0267 (11)0.0009 (8)0.0110 (9)0.0065 (8)
C220.0276 (11)0.0186 (10)0.0225 (10)0.0001 (9)0.0148 (9)0.0027 (8)
C230.0323 (11)0.0185 (11)0.0330 (11)0.0043 (9)0.0175 (10)0.0054 (9)
C240.0380 (12)0.0220 (12)0.0354 (12)0.0013 (10)0.0192 (10)0.0033 (10)
C250.0477 (14)0.0295 (13)0.0372 (13)0.0068 (11)0.0231 (11)0.0075 (10)
C260.0305 (12)0.0313 (13)0.0441 (13)0.0056 (10)0.0174 (10)0.0073 (11)
Geometric parameters (Å, º) top
O1—C61.327 (3)C7—H7B0.9700
O1—C71.447 (3)C8—H8D0.9600
O2—C61.202 (3)C8—H8E0.9600
O3—C91.341 (2)C8—H8F0.9600
O3—C101.473 (2)C10—C111.507 (3)
O4—C91.216 (2)C10—C131.508 (3)
O5—C171.328 (2)C10—C121.509 (3)
O5—C181.442 (3)C11—H11A0.9600
O6—C171.198 (3)C11—H11B0.9600
O7—C221.341 (2)C11—H11C0.9600
O7—C231.471 (2)C12—H12A0.9600
O8—C221.216 (2)C12—H12B0.9600
N1—C11.365 (3)C12—H12C0.9600
N1—C61.379 (3)C13—H13A0.9600
N1—N21.390 (2)C13—H13B0.9600
N2—C21.330 (3)C13—H13C0.9600
N3—C91.336 (3)C14—C151.430 (3)
N3—C51.471 (3)C15—C161.329 (3)
N3—C41.472 (2)C15—C211.486 (3)
N4—C21.347 (3)C16—C201.484 (3)
N4—H4"0.8999C18—C191.486 (4)
N4—H4'0.8999C18—H18A0.9700
N5—C161.365 (3)C18—H18B0.9700
N5—C171.373 (3)C19—H19A0.9600
N5—N61.393 (2)C19—H19B0.9600
N6—C141.330 (3)C19—H19C0.9600
N7—C221.339 (3)C20—H20A0.9700
N7—C211.473 (2)C20—H20B0.9700
N7—C201.477 (3)C21—H21A0.9700
N8—C141.338 (3)C21—H21B0.9700
N8—H8'0.8600C23—C241.504 (3)
N8—H8"0.8600C23—C261.511 (3)
C1—C31.329 (3)C23—C251.512 (3)
C1—C51.482 (3)C24—H24A0.9600
C2—C31.429 (3)C24—H24B0.9600
C3—C41.487 (3)C24—H24C0.9600
C4—H4D0.9700C25—H25A0.9600
C4—H4E0.9700C25—H25B0.9600
C5—H5A0.9700C25—H25C0.9600
C5—H5B0.9700C26—H26A0.9600
C7—C81.494 (4)C26—H26B0.9600
C7—H7A0.9700C26—H26C0.9600
C6—O1—C7116.59 (18)C10—C12—H12A109.5
C9—O3—C10120.85 (15)C10—C12—H12B109.5
C17—O5—C18117.13 (18)H12A—C12—H12B109.5
C22—O7—C23121.69 (16)C10—C12—H12C109.5
C1—N1—C6128.99 (18)H12A—C12—H12C109.5
C1—N1—N2110.17 (16)H12B—C12—H12C109.5
C6—N1—N2120.78 (17)C10—C13—H13A109.5
C2—N2—N1104.91 (16)C10—C13—H13B109.5
C9—N3—C5124.64 (17)H13A—C13—H13B109.5
C9—N3—C4120.16 (17)C10—C13—H13C109.5
C5—N3—C4114.81 (15)H13A—C13—H13C109.5
C2—N4—H4"121.4H13B—C13—H13C109.5
C2—N4—H4'119.3N6—C14—N8122.08 (18)
H4"—N4—H4'112.9N6—C14—C15110.37 (17)
C16—N5—C17128.92 (17)N8—C14—C15127.55 (19)
C16—N5—N6110.18 (16)C16—C15—C14106.07 (18)
C17—N5—N6120.77 (16)C16—C15—C21111.02 (17)
C14—N6—N5104.90 (16)C14—C15—C21142.89 (19)
C22—N7—C21121.67 (17)C15—C16—N5108.47 (17)
C22—N7—C20123.51 (16)C15—C16—C20114.67 (18)
C21—N7—C20114.55 (15)N5—C16—C20136.80 (18)
C14—N8—H8'120.0O6—C17—O5126.8 (2)
C14—N8—H8"120.0O6—C17—N5124.59 (19)
H8'—N8—H8"120.0O5—C17—N5108.57 (17)
C3—C1—N1108.48 (18)O5—C18—C19110.85 (19)
C3—C1—C5114.49 (19)O5—C18—H18A109.5
N1—C1—C5136.95 (19)C19—C18—H18A109.5
N2—C2—N4121.98 (19)O5—C18—H18B109.5
N2—C2—C3110.42 (18)C19—C18—H18B109.5
N4—C2—C3127.6 (2)H18A—C18—H18B108.1
C1—C3—C2106.00 (19)C18—C19—H19A109.5
C1—C3—C4111.15 (17)C18—C19—H19B109.5
C2—C3—C4142.74 (19)H19A—C19—H19B109.5
N3—C4—C3100.28 (16)C18—C19—H19C109.5
N3—C4—H4D111.7H19A—C19—H19C109.5
C3—C4—H4D111.7H19B—C19—H19C109.5
N3—C4—H4E111.7N7—C20—C1698.60 (15)
C3—C4—H4E111.7N7—C20—H20A112.0
H4D—C4—H4E109.5C16—C20—H20A112.0
N3—C5—C198.69 (16)N7—C20—H20B112.0
N3—C5—H5A112.0C16—C20—H20B112.0
C1—C5—H5A112.0H20A—C20—H20B109.7
N3—C5—H5B112.0N7—C21—C15100.59 (16)
C1—C5—H5B112.0N7—C21—H21A111.7
H5A—C5—H5B109.7C15—C21—H21A111.7
O2—C6—O1127.0 (2)N7—C21—H21B111.7
O2—C6—N1123.8 (2)C15—C21—H21B111.7
O1—C6—N1109.18 (18)H21A—C21—H21B109.4
O1—C7—C8111.1 (2)O8—C22—N7124.23 (18)
O1—C7—H7A109.4O8—C22—O7126.38 (18)
C8—C7—H7A109.4N7—C22—O7109.38 (18)
O1—C7—H7B109.4O7—C23—C24110.13 (16)
C8—C7—H7B109.4O7—C23—C26101.64 (17)
H7A—C7—H7B108.0C24—C23—C26109.97 (18)
C7—C8—H8D109.5O7—C23—C25109.88 (16)
C7—C8—H8E109.5C24—C23—C25112.93 (19)
H8D—C8—H8E109.5C26—C23—C25111.72 (18)
C7—C8—H8F109.5C23—C24—H24A109.5
H8D—C8—H8F109.5C23—C24—H24B109.5
H8E—C8—H8F109.5H24A—C24—H24B109.5
O4—C9—N3123.50 (18)C23—C24—H24C109.5
O4—C9—O3126.06 (18)H24A—C24—H24C109.5
N3—C9—O3110.43 (18)H24B—C24—H24C109.5
O3—C10—C11102.22 (16)C23—C25—H25A109.5
O3—C10—C13108.64 (16)C23—C25—H25B109.5
C11—C10—C13111.19 (16)H25A—C25—H25B109.5
O3—C10—C12111.02 (15)C23—C25—H25C109.5
C11—C10—C12110.14 (18)H25A—C25—H25C109.5
C13—C10—C12113.09 (18)H25B—C25—H25C109.5
C10—C11—H11A109.5C23—C26—H26A109.5
C10—C11—H11B109.5C23—C26—H26B109.5
H11A—C11—H11B109.5H26A—C26—H26B109.5
C10—C11—H11C109.5C23—C26—H26C109.5
H11A—C11—H11C109.5H26A—C26—H26C109.5
H11B—C11—H11C109.5H26B—C26—H26C109.5
C1—N1—N2—C20.5 (2)C9—O3—C10—C1367.0 (2)
C6—N1—N2—C2178.02 (18)C9—O3—C10—C1258.0 (2)
C16—N5—N6—C140.5 (2)N5—N6—C14—N8179.34 (19)
C17—N5—N6—C14176.67 (18)N5—N6—C14—C150.6 (2)
C6—N1—C1—C3177.6 (2)N6—C14—C15—C160.5 (2)
N2—N1—C1—C30.4 (2)N8—C14—C15—C16179.4 (2)
C6—N1—C1—C55.9 (4)N6—C14—C15—C21179.0 (3)
N2—N1—C1—C5176.8 (2)N8—C14—C15—C210.9 (4)
N1—N2—C2—N4178.65 (18)C14—C15—C16—N50.2 (2)
N1—N2—C2—C30.4 (2)C21—C15—C16—N5179.20 (16)
N1—C1—C3—C20.1 (2)C14—C15—C16—C20177.62 (17)
C5—C1—C3—C2177.45 (17)C21—C15—C16—C201.4 (3)
N1—C1—C3—C4177.00 (17)C17—N5—C16—C15175.96 (19)
C5—C1—C3—C40.4 (3)N6—N5—C16—C150.2 (2)
N2—C2—C3—C10.2 (2)C17—N5—C16—C207.0 (4)
N4—C2—C3—C1178.3 (2)N6—N5—C16—C20177.3 (2)
N2—C2—C3—C4175.7 (3)C18—O5—C17—O60.6 (3)
N4—C2—C3—C46.1 (4)C18—O5—C17—N5179.03 (17)
C9—N3—C4—C3165.54 (18)C16—N5—C17—O6180.0 (2)
C5—N3—C4—C37.5 (2)N6—N5—C17—O64.6 (3)
C1—C3—C4—N34.2 (2)C16—N5—C17—O50.4 (3)
C2—C3—C4—N3171.2 (3)N6—N5—C17—O5175.03 (16)
C9—N3—C5—C1165.14 (19)C17—O5—C18—C1986.1 (3)
C4—N3—C5—C17.6 (2)C22—N7—C20—C16166.46 (18)
C3—C1—C5—N34.7 (2)C21—N7—C20—C167.7 (2)
N1—C1—C5—N3171.7 (2)C15—C16—C20—N75.4 (2)
C7—O1—C6—O24.9 (3)N5—C16—C20—N7177.7 (2)
C7—O1—C6—N1174.19 (18)C22—N7—C21—C15167.14 (18)
C1—N1—C6—O2178.0 (2)C20—N7—C21—C157.1 (2)
N2—N1—C6—O20.9 (3)C16—C15—C21—N73.3 (2)
C1—N1—C6—O11.1 (3)C14—C15—C21—N7178.2 (3)
N2—N1—C6—O1178.17 (16)C21—N7—C22—O80.6 (3)
C6—O1—C7—C886.4 (2)C20—N7—C22—O8173.13 (19)
C5—N3—C9—O4179.44 (19)C21—N7—C22—O7179.94 (16)
C4—N3—C9—O48.2 (3)C20—N7—C22—O76.2 (3)
C5—N3—C9—O32.0 (3)C23—O7—C22—O812.3 (3)
C4—N3—C9—O3170.39 (16)C23—O7—C22—N7168.41 (16)
C10—O3—C9—O43.2 (3)C22—O7—C23—C2455.5 (2)
C10—O3—C9—N3178.21 (16)C22—O7—C23—C26172.01 (17)
C9—O3—C10—C11175.42 (17)C22—O7—C23—C2569.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8"···O4i0.862.253.069 (3)160
N8—H8···N2ii0.862.263.087 (3)163
N4—H4···N6iii0.902.253.104 (3)157
N4—H4"···O8iv0.902.363.233 (3)163
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x1, y1, z; (iv) x1, y, z.

Experimental details

Crystal data
Chemical formulaC13H20N4O4
Mr296.33
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)10.772 (3), 12.180 (4), 12.986 (4)
α, β, γ (°)70.845 (5), 65.875 (4), 85.821 (5)
V3)1465.2 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.06 × 0.05 × 0.04
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.994, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
7444, 5102, 3915
Rint0.026
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.128, 1.03
No. of reflections5102
No. of parameters387
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.32

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8"···O4i0.862.253.069 (3)160
N8—H8'···N2ii0.862.263.087 (3)163
N4—H4'···N6iii0.902.253.104 (3)157
N4—H4"···O8iv0.902.363.233 (3)163
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x1, y1, z; (iv) x1, y, z.
 

Acknowledgements

This work was supported by the National Natural Science Foundation (81072577).

References

First citationBruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFancelli, D., et al. (2005). J. Med. Chem. 48, 3080–3084.  Web of Science CrossRef PubMed CAS Google Scholar
First citationGadekar, S. M., Johnson, B. D. & Cohen, E. (1968). J. Med. Chem. 11, 616–618.  CrossRef CAS PubMed Web of Science Google Scholar
First citationGuo, X., Bai, X. G., Li, Y. L. & Wang, Y. C. (2010). Acta Cryst. E66, o1108.  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

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Volume 67| Part 5| May 2011| Page o1150
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