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ISSN: 2056-9890

1-(4-tert-Butyl­benz­yl)pyrimidine-2,4(1H,3H)-dione

aSchool of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China
*Correspondence e-mail: xcuwaller@163.com

(Received 10 January 2012; accepted 29 February 2012; online 14 March 2012)

The asymmetric unit of the title compound, C15H18N2O2, contains two independent mol­ecules with essentially identical geometries and conformations. The dihedral angles between the benzene and pyrimidine rings in the two mol­ecules are 89.96 (11) and 73.91 (11)°. The six methyl groups are disordered over two sets of sites, with site occupancies of 0.545 (4):0.455 (4) and 0.542 (7):0.458 (7) in the two mol­ecules. The crystal structure is stabilized by N—H⋯O hydrogen bonds.

Related literature

For the bioactivity of pyrimidine-2,4(1H,3H)-diones, see: Konz (1997[Konz, M. J. (1997). US Patent No. 5 683 966.]); Reinhard et al. (2004[Reinhard, R., Hamprecht, G., Puhl, M., Sagasser, I., Seitz, W., Zagar, C., Witschel, M. & Landes, A. (2004). WO Patent No. 2 004 007 467.]); Komori & Sanemitsu (2002[Komori, T. & Sanemitsu, Y. (2002). US Patent No. 6 403 534.]); Radatus & Karimian (1993[Radatus, B. K. & Karimian, K. (1993). WO Patent No. 9 300 351.]); Starrett et al. (1992[Starrett, J. J. E., Mansuri, M. M., Martin, J. C., Fuller, C. E. & Howell, H. G. (1992). US Patent No. 5 130 421.]). For a related structure, see: Li et al. (2005[Li, G.-C., Zhu, Y.-Q., Wang, Y.-F., Liu, W.-M., Song, H.-B. & Yang, H.-Z. (2005). Acta Cryst. E61, o4220-o4221.]).

[Scheme 1]

Experimental

Crystal data
  • C15H18N2O2

  • Mr = 258.31

  • Monoclinic, P 21 /c

  • a = 20.853 (7) Å

  • b = 10.013 (4) Å

  • c = 13.893 (5) Å

  • β = 94.915 (6)°

  • V = 2890.2 (18) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 294 K

  • 0.40 × 0.28 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.984

  • 14804 measured reflections

  • 5292 independent reflections

  • 2946 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.207

  • S = 1.02

  • 5292 reflections

  • 351 parameters

  • 186 restraints

  • H-atom parameters constrained

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O3i 0.86 2.06 2.915 (3) 174
N3—H3⋯O4ii 0.86 2.03 2.851 (3) 160
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART, 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

Derivatives of pyrimidine-2,4(1H,3H)-dione are very important molecules in biology and have many application in the areas of herbicide (Konz, 1997; Reinhard et al., 2004; Komori and Sanemitsu 2002). Derivatives of pyrimidine-2,4(1H,3H)-dione have also been developed as antiviral agents, shch as AZT which is the most widely used anti-AIDS drug (Radatus & Karimian, 1993) and stavudine which is the most widely used anti-HIV drug (Starrett et al., 1992). In order to discover further biologically active pyrimidine compounds, the title compound, (I), was synthesized and its crystal structure determined (Fig. 1).

In the crystal structure of the title molecule, The asymmetric unit contains two independent molecules, with essentially identical geometries and conformations. The dihedral angles between the benzene rings and the pyrimidine rings in the two molecules are 89.96 (0.11) and 73.91 (0.11)°. The six methyl groups are disordered over two positions, with site-occupancies of 0.545 (4):0.455 (4) and 0.542 (7):0.458 (7) in the two molecules. The crystal structure is stabilized by N—H···O hydrogen bonds. For a crystal structure related to the title compound, see: Li et al. (2005).

Related literature top

For the bioactivity of pyrimidine-2,4(1H,3H)-diones, see: Konz (1997); Reinhard et al. (2004); Komori & Sanemitsu (2002); Radatus & Karimian (1993); Starrett et al. (1992). For a related structure, see: Li et al. (2005).

Experimental top

Uracil (0.56 g, 5 mmol) and anhydrous potassium carbonate (0.84 g, 6 mmol) were mixed in N,N-dimethylformamide (20 ml). A solution of 4-tertbutylbenzyl chloride (0.92 g, 5 mmol) in acetone (10 ml) was then added dropwise, with stirring, at room temperature, and the mixture was stirred for another 10 h and then refluxed for 4 h. The solvent was evaporated in vacuo and the residue was washed with water. The resulting white precipitate was filtered off and purified by column chromatography on silica gel (petroleum ether:ethyl acetate = 2:1). The title compound was recrystallized from ethanol and single crystals of (I) were obtained.

Refinement top

All H atoms were placed in calculated positions, with C—H(aromatic) = 0.93 Å and C—H(aliphatic) = 0.96 Å or 0.97 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(C).

Structure description top

Derivatives of pyrimidine-2,4(1H,3H)-dione are very important molecules in biology and have many application in the areas of herbicide (Konz, 1997; Reinhard et al., 2004; Komori and Sanemitsu 2002). Derivatives of pyrimidine-2,4(1H,3H)-dione have also been developed as antiviral agents, shch as AZT which is the most widely used anti-AIDS drug (Radatus & Karimian, 1993) and stavudine which is the most widely used anti-HIV drug (Starrett et al., 1992). In order to discover further biologically active pyrimidine compounds, the title compound, (I), was synthesized and its crystal structure determined (Fig. 1).

In the crystal structure of the title molecule, The asymmetric unit contains two independent molecules, with essentially identical geometries and conformations. The dihedral angles between the benzene rings and the pyrimidine rings in the two molecules are 89.96 (0.11) and 73.91 (0.11)°. The six methyl groups are disordered over two positions, with site-occupancies of 0.545 (4):0.455 (4) and 0.542 (7):0.458 (7) in the two molecules. The crystal structure is stabilized by N—H···O hydrogen bonds. For a crystal structure related to the title compound, see: Li et al. (2005).

For the bioactivity of pyrimidine-2,4(1H,3H)-diones, see: Konz (1997); Reinhard et al. (2004); Komori & Sanemitsu (2002); Radatus & Karimian (1993); Starrett et al. (1992). For a related structure, see: Li et al. (2005).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 asymmetric unit of the title compound, (I), with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed line.
1-(4-tert-Butylbenzyl)pyrimidine-2,4(1H,3H)-dione top
Crystal data top
C15H18N2O2F(000) = 1104
Mr = 258.31Dx = 1.187 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3207 reflections
a = 20.853 (7) Åθ = 2.3–22.9°
b = 10.013 (4) ŵ = 0.08 mm1
c = 13.893 (5) ÅT = 294 K
β = 94.915 (6)°Prism, colourless
V = 2890.2 (18) Å30.40 × 0.28 × 0.20 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
5292 independent reflections
Radiation source: fine-focus sealed tube2946 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
phi and ω scansθmax = 25.4°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 2522
Tmin = 0.969, Tmax = 0.984k = 1012
14804 measured reflectionsl = 1616
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.207H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.093P)2 + 1.8764P]
where P = (Fo2 + 2Fc2)/3
5292 reflections(Δ/σ)max = 0.016
351 parametersΔρmax = 0.50 e Å3
186 restraintsΔρmin = 0.31 e Å3
Crystal data top
C15H18N2O2V = 2890.2 (18) Å3
Mr = 258.31Z = 8
Monoclinic, P21/cMo Kα radiation
a = 20.853 (7) ŵ = 0.08 mm1
b = 10.013 (4) ÅT = 294 K
c = 13.893 (5) Å0.40 × 0.28 × 0.20 mm
β = 94.915 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5292 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
2946 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.984Rint = 0.042
14804 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.063186 restraints
wR(F2) = 0.207H-atom parameters constrained
S = 1.02Δρmax = 0.50 e Å3
5292 reflectionsΔρmin = 0.31 e Å3
351 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*/UeqOcc. (<1)
O10.59221 (12)0.8165 (2)1.02506 (16)0.0590 (7)
O20.63012 (14)0.5542 (3)1.28734 (17)0.0779 (8)
O30.47352 (10)0.14989 (19)0.74452 (13)0.0439 (5)
O40.54683 (10)0.11521 (19)0.44745 (14)0.0468 (6)
N10.61343 (12)0.6826 (2)1.15484 (16)0.0424 (6)
H10.59030.73431.18730.051*
N20.65534 (12)0.6327 (3)1.00998 (17)0.0436 (6)
N30.51352 (11)0.1350 (2)0.59833 (15)0.0352 (6)
H30.50180.05260.59590.042*
N40.56191 (11)0.3135 (2)0.52653 (16)0.0358 (6)
C10.61872 (14)0.7185 (3)1.0607 (2)0.0390 (7)
C20.64043 (16)0.5741 (3)1.2041 (2)0.0501 (8)
C30.67929 (17)0.4932 (3)1.1461 (2)0.0593 (9)
H3A0.70110.41961.17320.071*
C40.68399 (16)0.5235 (3)1.0539 (2)0.0545 (9)
H40.70800.46761.01740.065*
C50.65428 (15)0.6492 (4)0.9050 (2)0.0528 (9)
H5A0.62740.72560.88610.063*
H5B0.63430.57100.87420.063*
C60.71906 (16)0.6689 (3)0.8674 (2)0.0481 (8)
C70.7650 (2)0.7498 (5)0.9107 (3)0.0859 (13)
H70.75800.79060.96900.103*
C80.8220 (2)0.7726 (5)0.8696 (3)0.0951 (14)
H80.85220.82920.90140.114*
C90.83593 (18)0.7163 (4)0.7849 (3)0.0681 (10)
C100.78888 (19)0.6360 (4)0.7410 (3)0.0739 (11)
H100.79550.59680.68200.089*
C110.73176 (17)0.6115 (4)0.7819 (2)0.0622 (10)
H110.70140.55490.75040.075*
C120.8989 (2)0.7414 (6)0.7402 (4)0.1158 (13)
C13A0.8921 (5)0.7427 (14)0.6299 (6)0.1189 (13)0.455 (4)
H13A0.87760.65680.60640.178*0.455 (4)
H13B0.93310.76260.60650.178*0.455 (4)
H13C0.86140.80960.60760.178*0.455 (4)
C13B0.9136 (5)0.6293 (10)0.6679 (7)0.1189 (13)0.545 (4)
H13D0.91270.54410.69950.178*0.545 (4)
H13E0.95540.64360.64580.178*0.545 (4)
H13F0.88180.63090.61370.178*0.545 (4)
C14A0.9290 (6)0.8780 (10)0.7697 (9)0.1189 (13)0.455 (4)
H14A0.89740.94700.75750.178*0.455 (4)
H14B0.96490.89510.73270.178*0.455 (4)
H14C0.94330.87680.83720.178*0.455 (4)
C14B0.8930 (5)0.8728 (9)0.6871 (8)0.1189 (13)0.545 (4)
H14D0.86040.86580.63430.178*0.545 (4)
H14E0.93340.89450.66260.178*0.545 (4)
H14F0.88150.94160.73050.178*0.545 (4)
C15A0.9492 (5)0.6380 (12)0.7739 (9)0.1189 (13)0.455 (4)
H15A0.95270.63330.84320.178*0.455 (4)
H15B0.99010.66300.75230.178*0.455 (4)
H15C0.93670.55230.74760.178*0.455 (4)
C15B0.9545 (4)0.7453 (12)0.8190 (6)0.1189 (13)0.545 (4)
H15D0.94940.82090.86010.178*0.545 (4)
H15E0.99440.75260.78990.178*0.545 (4)
H15F0.95450.66480.85650.178*0.545 (4)
C160.54110 (14)0.1835 (3)0.51971 (19)0.0349 (7)
C170.50240 (14)0.2044 (3)0.68156 (19)0.0356 (7)
C180.52587 (15)0.3387 (3)0.6835 (2)0.0428 (7)
H180.52250.39170.73780.051*
C190.55269 (14)0.3876 (3)0.6071 (2)0.0418 (7)
H190.56580.47640.60860.050*
C200.59296 (14)0.3704 (3)0.4448 (2)0.0416 (7)
H20A0.58940.46690.44640.050*
H20B0.57060.33930.38480.050*
C210.66279 (15)0.3322 (3)0.4470 (2)0.0423 (7)
C220.68630 (18)0.2626 (3)0.3729 (2)0.0585 (9)
H220.65820.23550.32100.070*
C230.7508 (2)0.2317 (4)0.3736 (3)0.0702 (11)
H230.76490.18410.32200.084*
C240.79479 (18)0.2687 (4)0.4475 (3)0.0666 (10)
C250.7703 (2)0.3357 (5)0.5223 (3)0.0950 (15)
H250.79800.36050.57520.114*
C260.70607 (19)0.3674 (5)0.5218 (3)0.0794 (13)
H260.69190.41410.57380.095*
C270.8656 (2)0.2326 (5)0.4482 (4)0.1145 (6)
C28A0.8853 (5)0.2512 (12)0.3424 (7)0.1154 (5)0.458 (7)
H28A0.86210.18840.30040.173*0.458 (7)
H28B0.93070.23620.34130.173*0.458 (7)
H28C0.87510.34040.32090.173*0.458 (7)
C28B0.8862 (5)0.1729 (11)0.3544 (7)0.1154 (5)0.542 (7)
H28D0.87560.07960.35160.173*0.542 (7)
H28E0.93190.18340.35240.173*0.542 (7)
H28F0.86430.21800.30030.173*0.542 (7)
C29A0.9086 (5)0.3213 (11)0.5155 (8)0.1154 (5)0.458 (7)
H29A0.89370.41190.50990.173*0.458 (7)
H29B0.95200.31630.49800.173*0.458 (7)
H29C0.90700.29150.58090.173*0.458 (7)
C29B0.9078 (5)0.3574 (9)0.4697 (8)0.1154 (5)0.542 (7)
H29D0.89690.42440.42170.173*0.542 (7)
H29E0.95240.33370.46840.173*0.542 (7)
H29F0.90060.39170.53240.173*0.542 (7)
C30A0.8739 (5)0.0849 (8)0.4731 (8)0.1154 (5)0.542 (7)
H30A0.85650.06720.53360.173*0.542 (7)
H30B0.91880.06250.47810.173*0.542 (7)
H30C0.85160.03190.42330.173*0.542 (7)
C30B0.8809 (5)0.1323 (11)0.5311 (8)0.1154 (5)0.458 (7)
H30D0.87880.17680.59190.173*0.458 (7)
H30E0.92340.09690.52730.173*0.458 (7)
H30F0.85020.06080.52570.173*0.458 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0835 (17)0.0448 (13)0.0513 (14)0.0173 (12)0.0200 (12)0.0114 (11)
O20.113 (2)0.0759 (18)0.0492 (15)0.0231 (16)0.0290 (14)0.0220 (13)
O30.0582 (13)0.0391 (12)0.0361 (11)0.0011 (10)0.0149 (10)0.0008 (9)
O40.0661 (14)0.0362 (11)0.0408 (12)0.0098 (10)0.0205 (10)0.0108 (9)
N10.0570 (16)0.0341 (13)0.0383 (14)0.0070 (12)0.0167 (11)0.0010 (11)
N20.0482 (15)0.0469 (15)0.0373 (14)0.0059 (12)0.0135 (11)0.0004 (12)
N30.0477 (14)0.0245 (12)0.0349 (13)0.0023 (10)0.0120 (11)0.0028 (10)
N40.0442 (14)0.0264 (12)0.0379 (13)0.0043 (10)0.0091 (11)0.0016 (10)
C10.0461 (18)0.0343 (16)0.0377 (16)0.0001 (14)0.0105 (13)0.0009 (13)
C20.065 (2)0.0451 (18)0.0418 (18)0.0046 (16)0.0123 (15)0.0103 (15)
C30.072 (2)0.052 (2)0.055 (2)0.0218 (17)0.0134 (17)0.0121 (16)
C40.063 (2)0.0496 (19)0.053 (2)0.0193 (17)0.0166 (16)0.0026 (16)
C50.0477 (19)0.074 (2)0.0381 (17)0.0025 (17)0.0093 (14)0.0032 (16)
C60.0503 (19)0.0573 (19)0.0381 (16)0.0006 (16)0.0106 (14)0.0018 (15)
C70.078 (3)0.117 (3)0.066 (2)0.027 (2)0.029 (2)0.038 (2)
C80.079 (3)0.126 (4)0.083 (3)0.041 (3)0.028 (2)0.030 (3)
C90.063 (2)0.085 (3)0.059 (2)0.007 (2)0.0228 (18)0.002 (2)
C100.074 (3)0.094 (3)0.058 (2)0.005 (2)0.0288 (19)0.014 (2)
C110.063 (2)0.074 (2)0.051 (2)0.0068 (19)0.0179 (17)0.0138 (18)
C120.083 (2)0.149 (3)0.122 (3)0.020 (2)0.047 (2)0.012 (3)
C13A0.086 (2)0.152 (3)0.125 (3)0.020 (2)0.046 (2)0.012 (2)
C13B0.086 (2)0.152 (3)0.125 (3)0.020 (2)0.046 (2)0.012 (2)
C14A0.086 (2)0.152 (3)0.125 (3)0.020 (2)0.046 (2)0.012 (2)
C14B0.086 (2)0.152 (3)0.125 (3)0.020 (2)0.046 (2)0.012 (2)
C15A0.086 (2)0.152 (3)0.125 (3)0.020 (2)0.046 (2)0.012 (2)
C15B0.086 (2)0.152 (3)0.125 (3)0.020 (2)0.046 (2)0.012 (2)
C160.0419 (17)0.0282 (15)0.0356 (16)0.0013 (12)0.0082 (12)0.0019 (12)
C170.0418 (17)0.0315 (15)0.0338 (15)0.0041 (13)0.0041 (13)0.0003 (12)
C180.056 (2)0.0330 (16)0.0403 (17)0.0023 (14)0.0091 (14)0.0102 (13)
C190.0512 (19)0.0276 (15)0.0473 (18)0.0039 (13)0.0082 (14)0.0082 (13)
C200.0535 (19)0.0327 (15)0.0403 (17)0.0048 (14)0.0145 (14)0.0030 (13)
C210.0511 (19)0.0334 (16)0.0440 (17)0.0083 (14)0.0133 (15)0.0022 (13)
C220.065 (2)0.060 (2)0.051 (2)0.0038 (18)0.0097 (17)0.0045 (17)
C230.076 (3)0.062 (2)0.077 (3)0.010 (2)0.032 (2)0.005 (2)
C240.053 (2)0.059 (2)0.090 (3)0.0041 (18)0.023 (2)0.000 (2)
C250.055 (3)0.129 (4)0.100 (3)0.010 (3)0.001 (2)0.041 (3)
C260.056 (3)0.105 (3)0.078 (3)0.008 (2)0.011 (2)0.042 (2)
C270.0693 (10)0.1021 (11)0.1757 (12)0.0096 (10)0.0308 (11)0.0051 (11)
C28A0.0702 (9)0.1029 (10)0.1765 (10)0.0100 (9)0.0305 (9)0.0050 (10)
C28B0.0702 (9)0.1029 (10)0.1765 (10)0.0100 (9)0.0305 (9)0.0050 (10)
C29A0.0702 (9)0.1029 (10)0.1765 (10)0.0100 (9)0.0305 (9)0.0050 (10)
C29B0.0702 (9)0.1029 (10)0.1765 (10)0.0100 (9)0.0305 (9)0.0050 (10)
C30A0.0702 (9)0.1029 (10)0.1765 (10)0.0100 (9)0.0305 (9)0.0050 (10)
C30B0.0702 (9)0.1029 (10)0.1765 (10)0.0100 (9)0.0305 (9)0.0050 (10)
Geometric parameters (Å, º) top
O1—C11.211 (3)C14B—H14E0.9600
O2—C21.210 (4)C14B—H14F0.9600
O3—C171.231 (3)C15A—H15A0.9600
O4—C161.229 (3)C15A—H15B0.9600
N1—C11.370 (4)C15A—H15C0.9600
N1—C21.378 (4)C15B—H15D0.9600
N1—H10.8600C15B—H15E0.9600
N2—C41.365 (4)C15B—H15F0.9600
N2—C11.382 (4)C17—C181.430 (4)
N2—C51.466 (4)C18—C191.335 (4)
N3—C161.366 (3)C18—H180.9300
N3—C171.386 (3)C19—H190.9300
N3—H30.8600C20—C211.503 (4)
N4—C191.370 (3)C20—H20A0.9700
N4—C161.373 (4)C20—H20B0.9700
N4—C201.469 (3)C21—C261.363 (5)
C2—C31.440 (4)C21—C221.369 (4)
C3—C41.328 (4)C22—C231.380 (5)
C3—H3A0.9300C22—H220.9300
C4—H40.9300C23—C241.367 (6)
C5—C61.503 (4)C23—H230.9300
C5—H5A0.9700C24—C251.371 (5)
C5—H5B0.9700C24—C271.519 (6)
C6—C71.355 (5)C25—C261.375 (6)
C6—C111.366 (4)C25—H250.9300
C7—C81.380 (5)C26—H260.9300
C7—H70.9300C27—C29A1.523 (8)
C8—C91.359 (5)C27—C30A1.525 (7)
C8—H80.9300C27—C28B1.529 (8)
C9—C101.371 (5)C27—C30B1.540 (8)
C9—C121.522 (6)C27—C29B1.543 (8)
C10—C111.384 (5)C27—C28A1.571 (8)
C10—H100.9300C28A—H28A0.9600
C11—H110.9300C28A—H28B0.9600
C12—C14B1.508 (8)C28A—H28C0.9600
C12—C15A1.519 (8)C28B—H28D0.9600
C12—C15B1.524 (8)C28B—H28E0.9600
C12—C13A1.527 (8)C28B—H28F0.9600
C12—C14A1.545 (8)C29A—H29A0.9600
C12—C13B1.554 (8)C29A—H29B0.9600
C13A—H13A0.9600C29A—H29C0.9600
C13A—H13B0.9600C29B—H29D0.9600
C13A—H13C0.9600C29B—H29E0.9600
C13B—H13D0.9600C29B—H29F0.9600
C13B—H13E0.9600C30A—H30A0.9600
C13B—H13F0.9600C30A—H30B0.9600
C14A—H14A0.9600C30A—H30C0.9600
C14A—H14B0.9600C30B—H30D0.9600
C14A—H14C0.9600C30B—H30E0.9600
C14B—H14D0.9600C30B—H30F0.9600
C1—N1—C2128.2 (3)C12—C15B—H15E109.5
C1—N1—H1115.9H15D—C15B—H15E109.5
C2—N1—H1115.9C12—C15B—H15F109.5
C4—N2—C1120.7 (2)H15D—C15B—H15F109.5
C4—N2—C5120.2 (3)H15E—C15B—H15F109.5
C1—N2—C5118.4 (3)O4—C16—N3122.2 (2)
C16—N3—C17126.9 (2)O4—C16—N4122.1 (2)
C16—N3—H3116.5N3—C16—N4115.7 (2)
C17—N3—H3116.5O3—C17—N3119.8 (2)
C19—N4—C16120.3 (2)O3—C17—C18126.2 (3)
C19—N4—C20121.6 (2)N3—C17—C18113.9 (2)
C16—N4—C20118.1 (2)C19—C18—C17119.8 (3)
O1—C1—N1122.1 (3)C19—C18—H18120.1
O1—C1—N2123.3 (3)C17—C18—H18120.1
N1—C1—N2114.6 (3)C18—C19—N4123.3 (3)
O2—C2—N1120.4 (3)C18—C19—H19118.4
O2—C2—C3126.6 (3)N4—C19—H19118.4
N1—C2—C3113.0 (3)N4—C20—C21112.1 (2)
C4—C3—C2120.2 (3)N4—C20—H20A109.2
C4—C3—H3A119.9C21—C20—H20A109.2
C2—C3—H3A119.9N4—C20—H20B109.2
C3—C4—N2123.3 (3)C21—C20—H20B109.2
C3—C4—H4118.4H20A—C20—H20B107.9
N2—C4—H4118.4C26—C21—C22116.7 (3)
N2—C5—C6115.1 (3)C26—C21—C20121.8 (3)
N2—C5—H5A108.5C22—C21—C20121.5 (3)
C6—C5—H5A108.5C21—C22—C23121.4 (4)
N2—C5—H5B108.5C21—C22—H22119.3
C6—C5—H5B108.5C23—C22—H22119.3
H5A—C5—H5B107.5C24—C23—C22122.4 (4)
C7—C6—C11117.1 (3)C24—C23—H23118.8
C7—C6—C5123.1 (3)C22—C23—H23118.8
C11—C6—C5119.7 (3)C23—C24—C25115.5 (4)
C6—C7—C8121.0 (4)C23—C24—C27121.9 (4)
C6—C7—H7119.5C25—C24—C27122.5 (4)
C8—C7—H7119.5C24—C25—C26122.4 (4)
C9—C8—C7123.0 (4)C24—C25—H25118.8
C9—C8—H8118.5C26—C25—H25118.8
C7—C8—H8118.5C21—C26—C25121.6 (4)
C8—C9—C10115.5 (4)C21—C26—H26119.2
C8—C9—C12122.8 (4)C25—C26—H26119.2
C10—C9—C12121.7 (4)C24—C27—C29A112.6 (6)
C9—C10—C11122.0 (3)C24—C27—C30A108.9 (5)
C9—C10—H10119.0C29A—C27—C30A112.2 (7)
C11—C10—H10119.0C24—C27—C28B115.6 (6)
C6—C11—C10121.3 (4)C24—C27—C30B107.5 (5)
C6—C11—H11119.3C28B—C27—C30B109.1 (6)
C10—C11—H11119.3C24—C27—C29B110.3 (5)
C14B—C12—C9107.9 (5)C28B—C27—C29B106.5 (6)
C15A—C12—C9111.0 (6)C30B—C27—C29B107.7 (7)
C14B—C12—C15B110.7 (6)C24—C27—C28A107.3 (6)
C9—C12—C15B109.9 (5)C29A—C27—C28A108.5 (6)
C9—C12—C13A113.7 (6)C30A—C27—C28A107.1 (6)
C15A—C12—C14A105.6 (6)C27—C28A—H28A109.5
C9—C12—C14A112.5 (5)C27—C28A—H28B109.5
C13A—C12—C14A105.0 (6)C27—C28A—H28C109.5
C14B—C12—C13B109.0 (6)C27—C28B—H28D109.5
C9—C12—C13B111.7 (5)C27—C28B—H28E109.5
C15B—C12—C13B107.7 (6)H28D—C28B—H28E109.5
C12—C13A—H13A109.5C27—C28B—H28F109.5
C12—C13A—H13B109.5H28D—C28B—H28F109.5
C12—C13A—H13C109.5H28E—C28B—H28F109.5
C12—C13B—H13D109.5C27—C29A—H29A109.5
C12—C13B—H13E109.5C27—C29A—H29B109.5
H13D—C13B—H13E109.5C27—C29A—H29C109.5
C12—C13B—H13F109.5C27—C29B—H29D109.5
H13D—C13B—H13F109.5C27—C29B—H29E109.5
H13E—C13B—H13F109.5H29D—C29B—H29E109.5
C12—C14A—H14A109.5C27—C29B—H29F109.5
C12—C14A—H14B109.5H29D—C29B—H29F109.5
C12—C14A—H14C109.5H29E—C29B—H29F109.5
C12—C14B—H14D109.5C27—C30A—H30A109.5
C12—C14B—H14E109.5C27—C30A—H30B109.5
H14D—C14B—H14E109.5C27—C30A—H30C109.5
C12—C14B—H14F109.5C27—C30B—H30D109.5
H14D—C14B—H14F109.5C27—C30B—H30E109.5
H14E—C14B—H14F109.5H30D—C30B—H30E109.5
C12—C15A—H15A109.5C27—C30B—H30F109.5
C12—C15A—H15B109.5H30D—C30B—H30F109.5
C12—C15A—H15C109.5H30E—C30B—H30F109.5
C12—C15B—H15D109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.062.915 (3)174
N3—H3···O4ii0.862.032.851 (3)160
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC15H18N2O2
Mr258.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)20.853 (7), 10.013 (4), 13.893 (5)
β (°) 94.915 (6)
V3)2890.2 (18)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.28 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.969, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
14804, 5292, 2946
Rint0.042
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.207, 1.02
No. of reflections5292
No. of parameters351
No. of restraints186
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.50, 0.31

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.8602.0572.915 (3)174
N3—H3···O4ii0.8602.0282.851 (3)160
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y, z+1.
 

Acknowledgements

This work was supported by the Natural Science Foundation of Henan Province China (grant No. 082300420110) and the Natural Science Foundation of Henan Province Eduation Department, China (grant No. 2007150036).

References

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First citationKonz, M. J. (1997). US Patent No. 5 683 966.  Google Scholar
First citationLi, G.-C., Zhu, Y.-Q., Wang, Y.-F., Liu, W.-M., Song, H.-B. & Yang, H.-Z. (2005). Acta Cryst. E61, o4220–o4221.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRadatus, B. K. & Karimian, K. (1993). WO Patent No. 9 300 351.  Google Scholar
First citationReinhard, R., Hamprecht, G., Puhl, M., Sagasser, I., Seitz, W., Zagar, C., Witschel, M. & Landes, A. (2004). WO Patent No. 2 004 007 467.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStarrett, J. J. E., Mansuri, M. M., Martin, J. C., Fuller, C. E. & Howell, H. G. (1992). US Patent No. 5 130 421.  Google Scholar

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