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There are two mol­ecules in the asymmetric unit of the title compound, C10H14N4OS. Both the thio­carbonyl and carbonyl groups are cis with respect to the C—N thio­urea bond. Both intra- and inter­molecular N—H...N hydrogen bonds stabilize the packing arrangement.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019459/hg2229sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019459/hg2229Isup2.hkl
Contains datablock I

CCDC reference: 647689

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.059
  • wR factor = 0.118
  • Data-to-parameter ratio = 17.1

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Comment top

The background to this study has been set out in our previous work for the structural chemistry of N,N'-disubstituted thioureas (Shoukat et al., 2007). Herein, as a continuation of these studies, the structure of the title compound (I) is described. A depiction of the molecule is given in Fig. 1. Bond lengths and angles, see the selected geometric parameters table, can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002; Khawar Rauf et al., 2006). The molecule exists in its thione form with typical thiourea C—S and C—O bond distances, as well as shortened C—N bonds (See geometric parameters table). The planes containing the S1, O1, N1, N2, C1 & C2 and S2, O2, N5, N6, C11 & C12 atoms are almost parallel to the pyrimidine ring, forming dihedral angles of 9.54 (13)° and 12.92 (12)° respectively. The molecules also feature intra & intermolecular N—H···N hydrogen bonds (See hydrogen-bond geometry table and Fig 2).

Related literature top

For related literature, see: Allen (2002); Khawar Rauf, Badshah & Flörke (2006); Shoukat et al. (2007).

Experimental top

Freshly prepared pivaloylisothiocyanate (1.43 g, 10 mmol) in acetone (30 ml) was stirred for 30 minutes. Neat 2-aminopyrimidine (1.0 g, 10 mmol) was then added and the resulting mixture was stirred for 1 h. The reaction mixture was poured into acidified water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol/ chloroform (1:5 v/v) to give fine crystals of (I), with an overall yield of 80%.

Refinement top

C-bound H atoms were included in the riding model approximation with C—H 0.95–0.98 Å, and with Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl). The N-bound H atoms were refined isotropically.

Structure description top

The background to this study has been set out in our previous work for the structural chemistry of N,N'-disubstituted thioureas (Shoukat et al., 2007). Herein, as a continuation of these studies, the structure of the title compound (I) is described. A depiction of the molecule is given in Fig. 1. Bond lengths and angles, see the selected geometric parameters table, can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002; Khawar Rauf et al., 2006). The molecule exists in its thione form with typical thiourea C—S and C—O bond distances, as well as shortened C—N bonds (See geometric parameters table). The planes containing the S1, O1, N1, N2, C1 & C2 and S2, O2, N5, N6, C11 & C12 atoms are almost parallel to the pyrimidine ring, forming dihedral angles of 9.54 (13)° and 12.92 (12)° respectively. The molecules also feature intra & intermolecular N—H···N hydrogen bonds (See hydrogen-bond geometry table and Fig 2).

For related literature, see: Allen (2002); Khawar Rauf, Badshah & Flörke (2006); Shoukat et al. (2007).

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and TEXSAN.

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing the atom labelling scheme. Thermal displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Hydrogen-bonded dimer structures of (I) viewed along the c-axis. The hydrogen bonds are shown as dashed lines.
1-Pivaloyl-3-(pyrimidin-2-yl)thiourea top
Crystal data top
C10H14N4OSZ = 4
Mr = 238.31F(000) = 504
Triclinic, P1Dx = 1.357 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 5.652 (3) ÅCell parameters from 3112 reflections
b = 11.674 (8) Åθ = 3.3–27.5°
c = 18.585 (12) ŵ = 0.26 mm1
α = 106.915 (9)°T = 113 K
β = 92.642 (6)°Block, yellow
γ = 94.478 (8)°0.45 × 0.36 × 0.20 mm
V = 1166.6 (13) Å3
Data collection top
Rigaku/MSC Mercury CCD
diffractometer
4314 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 27.5°, θmin = 3.3°
Detector resolution: 14.62 pixels mm-1h = 77
ω scansk = 159
9547 measured reflectionsl = 1824
5309 independent 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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0286P)2 + 1.3663P]
where P = (Fo2 + 2Fc2)/3
5309 reflections(Δ/σ)max < 0.001
311 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C10H14N4OSγ = 94.478 (8)°
Mr = 238.31V = 1166.6 (13) Å3
Triclinic, P1Z = 4
a = 5.652 (3) ÅMo Kα radiation
b = 11.674 (8) ŵ = 0.26 mm1
c = 18.585 (12) ÅT = 113 K
α = 106.915 (9)°0.45 × 0.36 × 0.20 mm
β = 92.642 (6)°
Data collection top
Rigaku/MSC Mercury CCD
diffractometer
4314 reflections with I > 2σ(I)
9547 measured reflectionsRint = 0.034
5309 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.33 e Å3
5309 reflectionsΔρmin = 0.32 e Å3
311 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
C10.0618 (4)0.4642 (2)0.17088 (13)0.0190 (5)
S10.17984 (11)0.37188 (6)0.16735 (4)0.02662 (16)
N10.1016 (3)0.50531 (18)0.10978 (11)0.0197 (4)
H10.010 (5)0.480 (3)0.0741 (17)0.032 (8)*
C20.2483 (4)0.4715 (2)0.29593 (13)0.0199 (5)
O10.1185 (3)0.39231 (16)0.30699 (10)0.0307 (4)
N20.2299 (4)0.50592 (18)0.23032 (11)0.0199 (4)
H20.339 (5)0.555 (3)0.2231 (16)0.029 (8)*
C30.2906 (4)0.5791 (2)0.09625 (13)0.0177 (5)
N30.4638 (3)0.62528 (18)0.15060 (11)0.0214 (4)
C40.6480 (4)0.6896 (2)0.13348 (14)0.0228 (5)
H4A0.77520.72400.17060.027*
C50.6579 (4)0.7071 (2)0.06343 (14)0.0231 (5)
H5A0.79100.75040.05090.028*
C60.4640 (4)0.6585 (2)0.01227 (13)0.0221 (5)
H6A0.46400.67140.03590.026*
N40.2768 (3)0.59406 (18)0.02747 (11)0.0206 (4)
C70.4417 (4)0.5426 (2)0.35636 (13)0.0217 (5)
C80.6106 (5)0.6306 (2)0.33193 (15)0.0302 (6)
H8A0.69190.58650.28840.045*
H8B0.72850.67160.37360.045*
H8C0.51970.69020.31810.045*
C90.3076 (5)0.6119 (3)0.42255 (15)0.0338 (6)
H9A0.42200.65660.46440.051*
H9B0.20200.55520.43900.051*
H9C0.21300.66830.40660.051*
C100.5839 (5)0.4511 (3)0.37960 (17)0.0340 (6)
H10A0.67010.40780.33700.051*
H10B0.47480.39380.39440.051*
H10C0.69760.49320.42230.051*
C110.2873 (4)0.0628 (2)0.32001 (13)0.0194 (5)
S20.05219 (11)0.15886 (6)0.31716 (3)0.02635 (16)
N50.4319 (3)0.01896 (18)0.38563 (11)0.0200 (4)
H50.386 (5)0.041 (2)0.4230 (16)0.021 (7)*
C120.2599 (4)0.0515 (2)0.18742 (13)0.0187 (5)
O20.1185 (3)0.13758 (16)0.15963 (10)0.0265 (4)
N60.3540 (4)0.01990 (19)0.26246 (11)0.0228 (5)
H60.470 (6)0.037 (3)0.2758 (18)0.043 (9)*
C130.6386 (4)0.0593 (2)0.40249 (13)0.0187 (5)
N70.7068 (4)0.11528 (18)0.35241 (11)0.0219 (4)
C140.9128 (4)0.1856 (2)0.37013 (14)0.0238 (5)
H14A0.96720.22700.33600.029*
C151.0473 (4)0.1998 (2)0.43597 (14)0.0243 (5)
H15A1.19570.24780.44740.029*
C160.9569 (4)0.1409 (2)0.48524 (14)0.0232 (5)
H16A1.04520.15040.53170.028*
N80.7501 (3)0.07114 (18)0.46991 (11)0.0210 (4)
C170.3594 (4)0.0349 (2)0.14560 (13)0.0198 (5)
C180.2489 (5)0.0087 (3)0.06439 (14)0.0295 (6)
H18A0.07530.01060.06460.044*
H18B0.29310.08960.03980.044*
H18C0.30760.04630.03680.044*
C190.6315 (4)0.0367 (2)0.14566 (14)0.0233 (5)
H19A0.69130.08780.11570.035*
H19B0.67490.04530.12380.035*
H19C0.70210.06870.19760.035*
C200.2929 (4)0.1612 (2)0.18413 (15)0.0262 (5)
H20A0.34650.21540.15530.039*
H20B0.36960.19000.23540.039*
H20C0.11980.15930.18650.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0185 (11)0.0198 (11)0.0187 (12)0.0015 (9)0.0006 (9)0.0061 (9)
S10.0229 (3)0.0307 (3)0.0262 (3)0.0091 (3)0.0049 (2)0.0124 (3)
N10.0176 (10)0.0227 (10)0.0183 (10)0.0048 (8)0.0051 (8)0.0080 (8)
C20.0215 (11)0.0200 (11)0.0175 (11)0.0007 (9)0.0019 (9)0.0048 (9)
O10.0358 (10)0.0309 (10)0.0266 (10)0.0112 (8)0.0034 (8)0.0151 (8)
N20.0199 (10)0.0208 (10)0.0191 (10)0.0050 (8)0.0024 (8)0.0084 (8)
C30.0166 (10)0.0170 (11)0.0185 (11)0.0009 (9)0.0024 (9)0.0048 (9)
N30.0214 (10)0.0226 (10)0.0195 (10)0.0044 (8)0.0051 (8)0.0079 (8)
C40.0200 (11)0.0226 (12)0.0247 (13)0.0030 (9)0.0041 (10)0.0074 (10)
C50.0202 (12)0.0233 (12)0.0250 (13)0.0056 (10)0.0023 (10)0.0082 (10)
C60.0254 (12)0.0240 (12)0.0168 (12)0.0017 (10)0.0010 (9)0.0076 (10)
N40.0204 (10)0.0211 (10)0.0196 (10)0.0024 (8)0.0018 (8)0.0064 (8)
C70.0204 (11)0.0259 (12)0.0192 (12)0.0004 (10)0.0016 (9)0.0081 (10)
C80.0297 (13)0.0345 (15)0.0257 (14)0.0107 (11)0.0079 (11)0.0128 (12)
C90.0361 (15)0.0399 (16)0.0205 (13)0.0007 (12)0.0014 (11)0.0023 (12)
C100.0252 (13)0.0451 (17)0.0395 (17)0.0043 (12)0.0023 (12)0.0249 (14)
C110.0205 (11)0.0211 (11)0.0162 (11)0.0020 (9)0.0018 (9)0.0063 (9)
S20.0259 (3)0.0327 (3)0.0196 (3)0.0122 (3)0.0041 (2)0.0112 (3)
N50.0212 (10)0.0236 (10)0.0163 (10)0.0053 (8)0.0017 (8)0.0098 (8)
C120.0164 (11)0.0247 (12)0.0148 (11)0.0019 (9)0.0015 (9)0.0057 (9)
O20.0268 (9)0.0295 (10)0.0202 (9)0.0101 (8)0.0032 (7)0.0065 (7)
N60.0239 (11)0.0258 (11)0.0184 (10)0.0089 (9)0.0041 (8)0.0101 (9)
C130.0204 (11)0.0189 (11)0.0159 (11)0.0014 (9)0.0002 (9)0.0048 (9)
N70.0240 (10)0.0233 (10)0.0182 (10)0.0054 (8)0.0015 (8)0.0084 (8)
C140.0269 (12)0.0230 (12)0.0215 (12)0.0029 (10)0.0026 (10)0.0077 (10)
C150.0231 (12)0.0237 (12)0.0238 (13)0.0065 (10)0.0004 (10)0.0062 (10)
C160.0236 (12)0.0230 (12)0.0205 (12)0.0018 (10)0.0021 (9)0.0040 (10)
N80.0209 (10)0.0236 (10)0.0178 (10)0.0011 (8)0.0013 (8)0.0064 (8)
C170.0156 (11)0.0269 (12)0.0186 (12)0.0002 (9)0.0008 (9)0.0105 (10)
C180.0251 (13)0.0475 (16)0.0176 (12)0.0026 (12)0.0007 (10)0.0143 (12)
C190.0187 (11)0.0300 (13)0.0226 (13)0.0019 (10)0.0014 (9)0.0102 (10)
C200.0248 (12)0.0291 (13)0.0291 (14)0.0033 (10)0.0041 (10)0.0148 (11)
Geometric parameters (Å, º) top
C1—N21.371 (3)C11—N61.362 (3)
C1—N11.376 (3)C11—N51.377 (3)
C1—S11.659 (2)C11—S21.659 (2)
N1—C31.397 (3)N5—C131.390 (3)
N1—H10.86 (3)N5—H50.85 (3)
C2—O11.206 (3)C12—O21.204 (3)
C2—N21.392 (3)C12—N61.402 (3)
C2—C71.532 (3)C12—C171.531 (3)
N2—H20.85 (3)N6—H60.86 (3)
C3—N31.334 (3)C13—N71.338 (3)
C3—N41.339 (3)C13—N81.341 (3)
N3—C41.340 (3)N7—C141.340 (3)
C4—C51.378 (3)C14—C151.371 (4)
C4—H4A0.9500C14—H14A0.9500
C5—C61.385 (3)C15—C161.388 (3)
C5—H5A0.9500C15—H15A0.9500
C6—N41.338 (3)C16—N81.340 (3)
C6—H6A0.9500C16—H16A0.9500
C7—C81.527 (3)C17—C201.525 (4)
C7—C101.531 (4)C17—C181.531 (3)
C7—C91.531 (4)C17—C191.537 (3)
C8—H8A0.9800C18—H18A0.9800
C8—H8B0.9800C18—H18B0.9800
C8—H8C0.9800C18—H18C0.9800
C9—H9A0.9800C19—H19A0.9800
C9—H9B0.9800C19—H19B0.9800
C9—H9C0.9800C19—H19C0.9800
C10—H10A0.9800C20—H20A0.9800
C10—H10B0.9800C20—H20B0.9800
C10—H10C0.9800C20—H20C0.9800
N2—C1—N1115.3 (2)N6—C11—N5114.8 (2)
N2—C1—S1125.97 (18)N6—C11—S2125.95 (18)
N1—C1—S1118.74 (17)N5—C11—S2119.27 (17)
C1—N1—C3131.0 (2)C11—N5—C13130.8 (2)
C1—N1—H1113.4 (19)C11—N5—H5115.6 (18)
C3—N1—H1115.6 (19)C13—N5—H5113.6 (18)
O1—C2—N2123.3 (2)O2—C12—N6123.2 (2)
O1—C2—C7120.3 (2)O2—C12—C17124.5 (2)
N2—C2—C7116.36 (19)N6—C12—C17112.29 (19)
C1—N2—C2127.9 (2)C11—N6—C12129.9 (2)
C1—N2—H2113.3 (19)C11—N6—H6113 (2)
C2—N2—H2118.6 (19)C12—N6—H6117 (2)
N3—C3—N4126.9 (2)N7—C13—N8126.4 (2)
N3—C3—N1118.6 (2)N7—C13—N5119.0 (2)
N4—C3—N1114.45 (19)N8—C13—N5114.59 (19)
C3—N3—C4116.5 (2)C13—N7—C14116.5 (2)
N3—C4—C5121.8 (2)N7—C14—C15122.1 (2)
N3—C4—H4A119.1N7—C14—H14A119.0
C5—C4—H4A119.1C15—C14—H14A119.0
C4—C5—C6116.7 (2)C14—C15—C16117.0 (2)
C4—C5—H5A121.6C14—C15—H15A121.5
C6—C5—H5A121.6C16—C15—H15A121.5
N4—C6—C5123.1 (2)N8—C16—C15122.7 (2)
N4—C6—H6A118.4N8—C16—H16A118.7
C5—C6—H6A118.4C15—C16—H16A118.7
C6—N4—C3114.94 (19)C16—N8—C13115.3 (2)
C8—C7—C10109.6 (2)C20—C17—C18109.8 (2)
C8—C7—C9109.5 (2)C20—C17—C12109.4 (2)
C10—C7—C9110.1 (2)C18—C17—C12108.02 (19)
C8—C7—C2114.9 (2)C20—C17—C19109.41 (19)
C10—C7—C2107.3 (2)C18—C17—C19109.7 (2)
C9—C7—C2105.3 (2)C12—C17—C19110.48 (19)
C7—C8—H8A109.5C17—C18—H18A109.5
C7—C8—H8B109.5C17—C18—H18B109.5
H8A—C8—H8B109.5H18A—C18—H18B109.5
C7—C8—H8C109.5C17—C18—H18C109.5
H8A—C8—H8C109.5H18A—C18—H18C109.5
H8B—C8—H8C109.5H18B—C18—H18C109.5
C7—C9—H9A109.5C17—C19—H19A109.5
C7—C9—H9B109.5C17—C19—H19B109.5
H9A—C9—H9B109.5H19A—C19—H19B109.5
C7—C9—H9C109.5C17—C19—H19C109.5
H9A—C9—H9C109.5H19A—C19—H19C109.5
H9B—C9—H9C109.5H19B—C19—H19C109.5
C7—C10—H10A109.5C17—C20—H20A109.5
C7—C10—H10B109.5C17—C20—H20B109.5
H10A—C10—H10B109.5H20A—C20—H20B109.5
C7—C10—H10C109.5C17—C20—H20C109.5
H10A—C10—H10C109.5H20A—C20—H20C109.5
H10B—C10—H10C109.5H20B—C20—H20C109.5
N2—C1—N1—C33.1 (4)N6—C11—N5—C132.0 (4)
S1—C1—N1—C3177.5 (2)S2—C11—N5—C13178.7 (2)
N1—C1—N2—C2173.5 (2)N5—C11—N6—C12174.7 (2)
S1—C1—N2—C27.1 (4)S2—C11—N6—C126.0 (4)
O1—C2—N2—C14.1 (4)O2—C12—N6—C1110.9 (4)
C7—C2—N2—C1174.2 (2)C17—C12—N6—C11169.7 (2)
C1—N1—C3—N33.5 (4)C11—N5—C13—N78.3 (4)
C1—N1—C3—N4175.7 (2)C11—N5—C13—N8172.2 (2)
N4—C3—N3—C42.9 (4)N8—C13—N7—C143.4 (4)
N1—C3—N3—C4176.2 (2)N5—C13—N7—C14177.2 (2)
C3—N3—C4—C50.1 (4)C13—N7—C14—C150.0 (4)
N3—C4—C5—C62.1 (4)N7—C14—C15—C162.1 (4)
C4—C5—C6—N42.0 (4)C14—C15—C16—N81.1 (4)
C5—C6—N4—C30.4 (4)C15—C16—N8—C131.8 (4)
N3—C3—N4—C63.0 (4)N7—C13—N8—C164.2 (4)
N1—C3—N4—C6176.1 (2)N5—C13—N8—C16176.3 (2)
O1—C2—C7—C8173.6 (2)O2—C12—C17—C20119.2 (3)
N2—C2—C7—C88.0 (3)N6—C12—C17—C2061.4 (3)
O1—C2—C7—C1051.5 (3)O2—C12—C17—C180.3 (3)
N2—C2—C7—C10130.1 (2)N6—C12—C17—C18179.1 (2)
O1—C2—C7—C965.8 (3)O2—C12—C17—C19120.3 (3)
N2—C2—C7—C9112.6 (2)N6—C12—C17—C1959.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N4i0.86 (3)2.27 (3)3.133 (3)174 (3)
N2—H2···N30.85 (3)1.90 (3)2.642 (3)144 (3)
N5—H5···N8ii0.85 (3)2.28 (3)3.122 (3)171 (2)
N6—H6···N70.86 (3)1.88 (3)2.632 (3)144 (3)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC10H14N4OS
Mr238.31
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)5.652 (3), 11.674 (8), 18.585 (12)
α, β, γ (°)106.915 (9), 92.642 (6), 94.478 (8)
V3)1166.6 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.45 × 0.36 × 0.20
Data collection
DiffractometerRigaku/MSC Mercury CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9547, 5309, 4314
Rint0.034
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.118, 1.10
No. of reflections5309
No. of parameters311
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.32

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2001), CrystalClear, TEXSAN (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97 and TEXSAN.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N4i0.86 (3)2.27 (3)3.133 (3)174 (3)
N2—H2···N30.85 (3)1.90 (3)2.642 (3)144 (3)
N5—H5···N8ii0.85 (3)2.28 (3)3.122 (3)171 (2)
N6—H6···N70.86 (3)1.88 (3)2.632 (3)144 (3)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+1.
 

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