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In the crystal structure of the title compound, C13H20N4O2, the two butyl groups are disordered over two positions, with site-occupancy ratios of 0.56 (2):0.44 (2) and 0.645 (3):0.355 (3). The mol­ecules are linked via weak inter­molecular N—H...N hydrogen bonds, to form a supra­molecular arrangement.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043334/at2387sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043334/at2387Isup2.hkl
Contains datablock I

CCDC reference: 663719

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.057
  • wR factor = 0.147
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT301_ALERT_3_B Main Residue Disorder ......................... 27.00 Perc.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.18 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 7 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 17.10 Deg. C10' -N2 -C10 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 16.10 Deg. C7' -C6 -C7 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. H6A -C6 -H6C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. H6B -C6 -H6D 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 111
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).

In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. In the crystal structurer, the molecules are linked via weak intermolecular N–H···N hydrogen bonds (Table 1), to form a supramolecular arrangement, as illustrated in Fig.2.

Related literature top

For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

Experimental top

1,3-Dibutyl-1H-purine-2,6(3H,7H)-dione (1 g) was added to an anhydrous N,N-dimethylformamide (50 ml), with stirring at 350 K. The resulting colourless solution was filtered and filtrate was allowed to stand in air at room temperature for one month, yielding colourless crystals of (I).

Refinement top

The two butyl (C6—C9) and (C10—C13) groups are disordered in two positions with the site-occupancy ratios of 0.564 (1)/0.436 (1) and 0.644 (1)/0.356 (1), respectively. In the disordered group, the C(methyl)-C(methyl) and C(methyl)-N(pyrimidine) distances were restrained to 1.54 (1) and 1.48 (1) Å, and the C and N atoms of the minor component were refined isotropically. The N-bound H atom was located in a difference Fourier map and refined freely. C-bound H atoms were included in calculated positions, with C—H = 0.93 (aromatic) or 0.96 Å (methyl), and refined using a riding model, with Uiso(H) = 1.2Ueq(C) for aromatic H or 1.5Ueq(C) for methyl H atoms.

Structure description top

In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).

In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. In the crystal structurer, the molecules are linked via weak intermolecular N–H···N hydrogen bonds (Table 1), to form a supramolecular arrangement, as illustrated in Fig.2.

For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top
[Figure 1] Fig. 1. The structure of the title molecule (I). Displacement ellipsoids are drawn at the 30% probability level. For clarity, only the major disorder components of the atoms are depicted.
[Figure 2] Fig. 2. The crystal packing of (I), viwed down the b axis. Hydrogen bonds are indicated by dashed lines.
1,3-Dibutyl-1H-purine-2,6(3H,7H)-dione top
Crystal data top
C13H20N4O2F(000) = 568
Mr = 264.33Dx = 1.246 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 2683 reflections
a = 14.2300 (14) Åθ = 2.6–27.9°
b = 9.4120 (8) ŵ = 0.09 mm1
c = 10.728 (1) ÅT = 113 K
β = 101.290 (4)°Block, colourless
V = 1409.0 (2) Å30.32 × 0.30 × 0.16 mm
Z = 4
Data collection top
Rigaku Saturn
diffractometer
3070 independent reflections
Radiation source: rotating anode2515 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.042
Detector resolution: 7.31 pixels mm-1θmax = 27.0°, θmin = 2.6°
ω scansh = 1818
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1211
Tmin = 0.973, Tmax = 0.986l = 1313
12057 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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0761P)2 + 0.1029P]
where P = (Fo2 + 2Fc2)/3
3070 reflections(Δ/σ)max < 0.001
245 parametersΔρmax = 0.21 e Å3
111 restraintsΔρmin = 0.23 e Å3
Crystal data top
C13H20N4O2V = 1409.0 (2) Å3
Mr = 264.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.2300 (14) ŵ = 0.09 mm1
b = 9.4120 (8) ÅT = 113 K
c = 10.728 (1) Å0.32 × 0.30 × 0.16 mm
β = 101.290 (4)°
Data collection top
Rigaku Saturn
diffractometer
3070 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2515 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.986Rint = 0.042
12057 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057111 restraints
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.21 e Å3
3070 reflectionsΔρmin = 0.23 e Å3
245 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)
O10.38973 (8)0.87003 (12)0.49767 (10)0.0374 (3)
O20.25608 (11)0.47462 (15)0.28230 (11)0.0601 (4)
N10.32215 (9)0.67085 (15)0.39159 (12)0.0360 (4)
N20.35377 (10)0.43656 (14)0.47432 (12)0.0367 (4)
N30.48557 (9)0.66280 (14)0.70573 (12)0.0293 (3)
N40.45896 (10)0.42872 (13)0.68474 (12)0.0349 (3)
C10.38066 (11)0.74015 (17)0.49472 (13)0.0308 (4)
C20.30763 (13)0.52338 (19)0.37712 (15)0.0416 (4)
C30.41034 (11)0.49831 (17)0.57962 (14)0.0311 (4)
C40.42479 (11)0.64183 (16)0.58947 (14)0.0289 (4)
C50.50294 (11)0.53407 (16)0.75810 (15)0.0332 (4)
H5A0.54250.51880.83920.040*
C60.27299 (11)0.76074 (19)0.28581 (15)0.0395 (4)
H6A0.26230.70510.20930.047*0.56 (2)
H6B0.31430.83830.27450.047*0.56 (2)
H6C0.26230.70510.20930.047*0.44 (2)
H6D0.31430.83830.27450.047*0.44 (2)
C70.1760 (4)0.8211 (10)0.3046 (8)0.0415 (16)0.56 (2)
H7A0.13040.74190.30570.050*0.56 (2)
H7B0.18480.87010.38780.050*0.56 (2)
C80.1341 (4)0.9254 (11)0.1991 (8)0.0501 (18)0.56 (2)
H8A0.12910.87680.11620.060*0.56 (2)
H8B0.17941.00560.20080.060*0.56 (2)
C90.0357 (4)0.9851 (14)0.2079 (7)0.061 (2)0.56 (2)
H9A0.01391.04970.13640.091*0.56 (2)
H9B0.04021.03710.28800.091*0.56 (2)
H9C0.01020.90690.20480.091*0.56 (2)
C100.3504 (3)0.2772 (4)0.4671 (7)0.0349 (11)0.645 (3)
H10A0.41410.23810.50490.042*0.645 (3)
H10B0.33450.24740.37690.042*0.645 (3)
C110.2754 (2)0.2176 (3)0.5377 (3)0.0381 (7)0.645 (3)
H11A0.27960.11260.53840.046*0.645 (3)
H11B0.29050.25060.62700.046*0.645 (3)
C120.1739 (2)0.2610 (3)0.4795 (3)0.0429 (8)0.645 (3)
H12A0.15830.22740.39040.051*0.645 (3)
H12B0.16950.36590.47850.051*0.645 (3)
C130.1011 (2)0.2008 (5)0.5521 (3)0.0639 (11)0.645 (3)
H13A0.03650.23120.51100.096*0.645 (3)
H13B0.11530.23550.63980.096*0.645 (3)
H13C0.10440.09680.55200.096*0.645 (3)
C7'0.1682 (4)0.7800 (13)0.2886 (10)0.038 (2)0.44 (2)
H7'A0.16090.82440.36990.045*0.44 (2)
H7'B0.13560.68660.28140.045*0.44 (2)
C8'0.1235 (5)0.8757 (13)0.1765 (9)0.045 (2)0.44 (2)
H8'A0.16340.96190.17610.054*0.44 (2)
H8'B0.12220.82430.09560.054*0.44 (2)
C9'0.0225 (5)0.9189 (16)0.1858 (9)0.056 (2)0.44 (2)
H9'A0.00620.97360.11030.085*0.44 (2)
H9'B0.02440.97730.26190.085*0.44 (2)
H9'C0.01600.83360.19140.085*0.44 (2)
C10'0.3200 (5)0.2900 (8)0.4624 (12)0.032 (2)0.355 (3)
H10C0.37230.22760.50570.039*0.355 (3)
H10D0.30660.26420.37120.039*0.355 (3)
C11'0.2311 (4)0.2593 (5)0.5160 (5)0.0303 (12)0.355 (3)
H11C0.18080.32960.48220.036*0.355 (3)
H11D0.24650.26920.60960.036*0.355 (3)
C12'0.1934 (3)0.1097 (5)0.4812 (4)0.0349 (12)0.355 (3)
H12C0.17860.10000.38750.042*0.355 (3)
H12D0.24390.03980.51510.042*0.355 (3)
C13'0.1040 (3)0.0768 (6)0.5334 (5)0.0423 (14)0.355 (3)
H13D0.08570.02260.51560.063*0.355 (3)
H13E0.05160.13900.49280.063*0.355 (3)
H13F0.11700.09280.62540.063*0.355 (3)
H30.5081 (14)0.755 (2)0.7458 (18)0.052 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0494 (7)0.0245 (7)0.0324 (6)0.0049 (5)0.0065 (5)0.0055 (5)
O20.0935 (10)0.0496 (9)0.0263 (7)0.0352 (7)0.0149 (6)0.0034 (6)
N10.0468 (8)0.0326 (8)0.0238 (7)0.0123 (6)0.0046 (6)0.0061 (6)
N20.0573 (9)0.0245 (8)0.0243 (7)0.0140 (6)0.0021 (6)0.0006 (5)
N30.0398 (7)0.0183 (7)0.0254 (7)0.0001 (5)0.0046 (5)0.0004 (5)
N40.0506 (8)0.0204 (7)0.0292 (7)0.0015 (6)0.0029 (6)0.0000 (5)
C10.0381 (8)0.0260 (9)0.0255 (8)0.0064 (6)0.0005 (6)0.0031 (6)
C20.0604 (11)0.0355 (10)0.0248 (8)0.0206 (8)0.0017 (7)0.0015 (7)
C30.0436 (8)0.0241 (8)0.0232 (8)0.0053 (6)0.0006 (6)0.0009 (6)
C40.0376 (8)0.0235 (8)0.0229 (8)0.0040 (6)0.0007 (6)0.0002 (6)
C50.0454 (9)0.0214 (8)0.0282 (8)0.0028 (6)0.0038 (6)0.0008 (6)
C60.0436 (9)0.0445 (11)0.0259 (8)0.0127 (7)0.0041 (7)0.0134 (7)
C70.038 (2)0.049 (3)0.032 (3)0.027 (2)0.0045 (16)0.010 (2)
C80.039 (2)0.069 (4)0.037 (3)0.005 (2)0.0061 (17)0.022 (3)
C90.045 (2)0.085 (5)0.046 (3)0.001 (3)0.0051 (18)0.013 (3)
C100.052 (3)0.0205 (17)0.0289 (17)0.0143 (17)0.000 (2)0.0012 (13)
C110.0515 (19)0.0304 (17)0.0293 (15)0.0069 (13)0.0006 (14)0.0045 (12)
C120.0546 (19)0.0445 (18)0.0288 (15)0.0035 (15)0.0063 (14)0.0047 (12)
C130.064 (2)0.076 (3)0.054 (2)0.0054 (18)0.0149 (16)0.0183 (18)
C7'0.036 (3)0.049 (4)0.023 (3)0.025 (3)0.0071 (18)0.009 (3)
C8'0.036 (3)0.062 (5)0.033 (3)0.012 (3)0.002 (2)0.010 (3)
C9'0.046 (3)0.078 (6)0.041 (3)0.005 (3)0.001 (2)0.000 (4)
C10'0.034 (4)0.034 (3)0.028 (3)0.006 (3)0.003 (3)0.008 (2)
C11'0.038 (3)0.028 (3)0.022 (3)0.001 (2)0.001 (2)0.001 (2)
C12'0.041 (2)0.030 (3)0.031 (2)0.0093 (18)0.0019 (18)0.0001 (19)
C13'0.041 (2)0.046 (3)0.039 (3)0.016 (2)0.006 (2)0.007 (2)
Geometric parameters (Å, º) top
O1—C11.2290 (18)C10—H10A0.9900
O2—C21.2212 (18)C10—H10B0.9900
N1—C21.407 (2)C11—C121.513 (4)
N1—C11.4079 (18)C11—H11A0.9900
N1—C61.4772 (19)C11—H11B0.9900
N2—C31.3805 (19)C12—C131.523 (4)
N2—C21.385 (2)C12—H12A0.9900
N2—C10'1.458 (7)C12—H12B0.9900
N2—C101.502 (4)C13—H13A0.9800
N3—C51.338 (2)C13—H13B0.9800
N3—C41.3858 (19)C13—H13C0.9800
N3—H30.99 (2)C7'—C8'1.538 (7)
N4—C51.3422 (19)C7'—H7'A0.9900
N4—C31.3689 (19)C7'—H7'B0.9900
C1—C41.426 (2)C8'—C9'1.516 (7)
C3—C41.367 (2)C8'—H8'A0.9900
C5—H5A0.9500C8'—H8'B0.9900
C6—C7'1.508 (6)C9'—H9'A0.9800
C6—C71.542 (6)C9'—H9'B0.9800
C6—H6A0.9600C9'—H9'C0.9800
C6—H6B0.9599C10'—C11'1.516 (7)
C6—H6C0.9600C10'—H10C0.9900
C6—H6D0.9599C10'—H10D0.9900
C7—C81.528 (6)C11'—C12'1.527 (5)
C7—H7A0.9900C11'—H11C0.9900
C7—H7B0.9900C11'—H11D0.9900
C8—C91.530 (6)C12'—C13'1.519 (5)
C8—H8A0.9900C12'—H12C0.9900
C8—H8B0.9900C12'—H12D0.9900
C9—H9A0.9800C13'—H13D0.9800
C9—H9B0.9800C13'—H13E0.9800
C9—H9C0.9800C13'—H13F0.9800
C10—C111.531 (5)
C2—N1—C1126.51 (13)N2—C10—C11111.0 (4)
C2—N1—C6116.29 (13)N2—C10—H10A109.4
C1—N1—C6117.17 (13)C11—C10—H10A109.4
C3—N2—C2118.84 (14)N2—C10—H10B109.4
C3—N2—C10'126.8 (5)C11—C10—H10B109.4
C2—N2—C10'113.1 (5)H10A—C10—H10B108.0
C3—N2—C10118.1 (3)C12—C11—C10113.5 (3)
C2—N2—C10123.0 (3)C12—C11—H11A108.9
C10'—N2—C1017.1 (4)C10—C11—H11A108.9
C5—N3—C4106.28 (13)C12—C11—H11B108.9
C5—N3—H3126.3 (11)C10—C11—H11B108.9
C4—N3—H3127.3 (11)H11A—C11—H11B107.7
C5—N4—C3103.42 (12)C11—C12—C13112.3 (3)
O1—C1—N1121.60 (13)C11—C12—H12A109.1
O1—C1—C4126.71 (14)C13—C12—H12A109.1
N1—C1—C4111.69 (13)C11—C12—H12B109.1
O2—C2—N2121.63 (16)C13—C12—H12B109.1
O2—C2—N1120.91 (16)H12A—C12—H12B107.9
N2—C2—N1117.46 (13)C6—C7'—C8'108.3 (6)
C4—C3—N4111.40 (13)C6—C7'—H7'A110.0
C4—C3—N2122.27 (14)C8'—C7'—H7'A110.0
N4—C3—N2126.33 (15)C6—C7'—H7'B110.0
C3—C4—N3105.56 (13)C8'—C7'—H7'B110.0
C3—C4—C1123.19 (13)H7'A—C7'—H7'B108.4
N3—C4—C1131.24 (14)C9'—C8'—C7'110.9 (6)
N3—C5—N4113.34 (13)C9'—C8'—H8'A109.5
N3—C5—H5A123.3C7'—C8'—H8'A109.5
N4—C5—H5A123.3C9'—C8'—H8'B109.5
N1—C6—C7'112.0 (3)C7'—C8'—H8'B109.5
N1—C6—C7114.3 (3)H8'A—C8'—H8'B108.0
C7'—C6—C716.1 (4)C8'—C9'—H9'A109.5
N1—C6—H6A108.4C8'—C9'—H9'B109.5
C7'—C6—H6A95.2H9'A—C9'—H9'B109.5
C7—C6—H6A108.5C8'—C9'—H9'C109.5
N1—C6—H6B108.8H9'A—C9'—H9'C109.5
C7'—C6—H6B123.0H9'B—C9'—H9'C109.5
C7—C6—H6B108.9N2—C10'—C11'115.6 (6)
H6A—C6—H6B107.7N2—C10'—H10C108.4
N1—C6—H6C108.4C11'—C10'—H10C108.4
C7'—C6—H6C95.2N2—C10'—H10D108.4
C7—C6—H6C108.5C11'—C10'—H10D108.4
H6A—C6—H6C0.0H10C—C10'—H10D107.4
H6B—C6—H6C107.7C10'—C11'—C12'111.3 (5)
N1—C6—H6D108.8C10'—C11'—H11C109.4
C7'—C6—H6D123.0C12'—C11'—H11C109.4
C7—C6—H6D108.9C10'—C11'—H11D109.4
H6A—C6—H6D107.7C12'—C11'—H11D109.4
H6B—C6—H6D0.0H11C—C11'—H11D108.0
H6C—C6—H6D107.7C13'—C12'—C11'112.2 (4)
C8—C7—C6111.6 (5)C13'—C12'—H12C109.2
C8—C7—H7A109.3C11'—C12'—H12C109.2
C6—C7—H7A109.3C13'—C12'—H12D109.2
C8—C7—H7B109.3C11'—C12'—H12D109.2
C6—C7—H7B109.3H12C—C12'—H12D107.9
H7A—C7—H7B108.0C12'—C13'—H13D109.5
C7—C8—C9114.8 (5)C12'—C13'—H13E109.5
C7—C8—H8A108.6H13D—C13'—H13E109.5
C9—C8—H8A108.6C12'—C13'—H13F109.5
C7—C8—H8B108.6H13D—C13'—H13F109.5
C9—C8—H8B108.6H13E—C13'—H13F109.5
H8A—C8—H8B107.5
C2—N1—C1—O1178.94 (15)C5—N3—C4—C1177.99 (16)
C6—N1—C1—O10.8 (2)O1—C1—C4—C3179.40 (16)
C2—N1—C1—C41.2 (2)N1—C1—C4—C30.5 (2)
C6—N1—C1—C4179.29 (13)O1—C1—C4—N31.1 (3)
C3—N2—C2—O2179.37 (16)N1—C1—C4—N3178.77 (15)
C10'—N2—C2—O211.1 (4)C4—N3—C5—N40.62 (18)
C10—N2—C2—O24.7 (3)C3—N4—C5—N30.42 (18)
C3—N2—C2—N10.5 (2)C2—N1—C6—C7'78.2 (6)
C10'—N2—C2—N1168.7 (4)C1—N1—C6—C7'103.5 (6)
C10—N2—C2—N1175.4 (3)C2—N1—C6—C795.6 (4)
C1—N1—C2—O2178.94 (16)C1—N1—C6—C786.1 (4)
C6—N1—C2—O20.8 (2)N1—C6—C7—C8173.9 (4)
C1—N1—C2—N21.2 (2)C7'—C6—C7—C8101 (2)
C6—N1—C2—N2179.30 (14)C6—C7—C8—C9177.5 (5)
C5—N4—C3—C40.05 (18)C3—N2—C10—C1185.2 (4)
C5—N4—C3—N2179.53 (15)C2—N2—C10—C1198.8 (4)
C2—N2—C3—C42.1 (2)C10'—N2—C10—C1140 (2)
C10'—N2—C3—C4168.5 (4)N2—C10—C11—C1264.2 (5)
C10—N2—C3—C4174.0 (3)C10—C11—C12—C13179.7 (3)
C2—N2—C3—N4178.47 (15)N1—C6—C7'—C8'179.4 (4)
C10'—N2—C3—N412.0 (5)C7—C6—C7'—C8'77.8 (19)
C10—N2—C3—N45.4 (3)C6—C7'—C8'—C9'170.8 (6)
N4—C3—C4—N30.31 (18)C3—N2—C10'—C11'82.6 (8)
N2—C3—C4—N3179.20 (14)C2—N2—C10'—C11'84.5 (9)
N4—C3—C4—C1178.37 (14)C10—N2—C10'—C11'147 (3)
N2—C3—C4—C12.1 (2)N2—C10'—C11'—C12'171.5 (7)
C5—N3—C4—C30.54 (17)C10'—C11'—C12'—C13'179.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N4i0.99 (2)1.82 (2)2.8115 (19)176.0 (18)
Symmetry code: (i) x+1, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC13H20N4O2
Mr264.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)14.2300 (14), 9.4120 (8), 10.728 (1)
β (°) 101.290 (4)
V3)1409.0 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.32 × 0.30 × 0.16
Data collection
DiffractometerRigaku Saturn
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.973, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
12057, 3070, 2515
Rint0.042
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.147, 1.11
No. of reflections3070
No. of parameters245
No. of restraints111
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.23

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N4i0.99 (2)1.82 (2)2.8115 (19)176.0 (18)
Symmetry code: (i) x+1, y+1/2, z+3/2.
 

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