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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Pages o2334-o2335
https://doi.org/10.1107/S1600536812029716

6-Amino-1,3-di­methyl-5-[(E)-2-(methyl­sulfan­yl)benzyl­­idene­amino]­pyrimidine-2,4(1H,3H)-dione–1,3,7,9-tetra­methyl­pyrimido[5,4-g]pteridine-2,4,6,8-tetrone (1/1)

Irvin N. Booysen,a Muhammed B. Ismaila and Matthew P. Akermana*

aUniversity of KwaZulu-Natal, School of Chemistry and Physics, Private Bag X01, Scottsville 3209, Pietermaritzburg, South Africa
*Correspondence e-mail: akermanm@ukzn.ac.za

(Received 18 June 2012; accepted 29 June 2012; online 4 July 2012)

In the title co-crystal, C12H12N6O4·C14H16N4O2S, both mol­ecules are essentially planar [maximum deviations = 0.129 (1) and 0.097 (1) Å, respectively]. The tricyclic and Schiff base mol­ecules are alternately stacked along the a axis and are linked by π–π inter­actions with centroid–centroid distances of 3.5170 (16) and 3.6576 (17) Å. An intra­molecular C—H⋯O hydrogen bond and a C—H⋯S contact occur in the Schiff base molecule. In the crystal, N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds lead to the formation of a three-dimensional network.

Related literature

For the crystal structure of a Schiff base derived from 5,6-diamino-1,3-dimethyl­pyrimidine-2,4(1H,3H)-dione and pico­lin­aldehyde, see: Booysen et al. (2011a[Booysen, I., Muhammed, I., Soares, A., Gerber, T., Hosten, E. & Betz, R. (2011a). Acta Cryst. E67, o1592.]). For the crystal structure of the title Schiff base, see: Booysen et al. (2011b[Booysen, I., Hlela, T., Ismail, M., Gerber, T., Hosten, E. & Betz, R. (2011b). Acta Cryst. E67, o2289.]). For the crystal structure of the title tricyclic compound, see: Booysen et al. (2008[Booysen, I., Gerber, T. & Mayer, P. (2008). J. Braz. Chem. Soc. 19, 199-202.]). For details of the use of the Schiff base N-(2-amino­benzyl­idene)-5-amino-1,3-dimethyl­pyrimidine-2,4(1H,3H)-dione as a che­lating ligand towards rhenium, see: Mayer et al. (2010[Mayer, P., Hosten, E., Gerber, T. I. A. & Booysen, I. (2010). J. Iran. Chem. Soc. 7, 775-780.]). For applications of Schiff base ligands, see: Kumar et al.. 2009[Kumar, S., Dhar, D. N. & Saxena, P. N. (2009). J. Sci. Ind. Res. 68, 181-187.].

[Scheme 1]

Experimental

Crystal data

  • C12H12N6O4·C14H16N4O2S

  • Mr = 608.64

  • Monoclinic, P 21 /n

  • a = 6.8501 (9) Å

  • b = 25.594 (4) Å

  • c = 15.284 (2) Å

  • β = 99.315 (5)°

  • V = 2644.3 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 100 K

  • 0.30 × 0.05 × 0.05 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2010[Bruker (2010). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.946, Tmax = 0.991

  • 14953 measured reflections

  • 5846 independent reflections

  • 4076 reflections with I > 2σ(I)

  • Rint = 0.057
Refinement

  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.171

  • S = 1.01

  • 5846 reflections

  • 403 parameters

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

  • Δρmax = 0.42 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2A—H101⋯N1A 0.85 (4) 2.32 (3) 2.701 (4) 107 (2)
N2A—H101⋯O2Bi 0.85 (4) 2.37 (3) 3.078 (3) 141 (3)
N2A—H102⋯O4Ai 0.96 (4) 2.29 (4) 3.238 (3) 169 (3)
C4A—H2⋯O2Aii 0.95 2.58 3.159 (4) 119
C3A—H3⋯O2Aii 0.95 2.49 3.114 (4) 123
C12A—H2′3⋯O4Ai 0.98 2.36 3.014 (4) 123
C1A—H5⋯O2Bi 0.95 2.45 3.339 (4) 155
C7A—H7⋯S1 0.95 2.59 3.017 (3) 108
C7A—H7⋯O1A 0.95 2.18 2.849 (3) 127
C13B—H5A1⋯O2Bi 0.98 2.50 3.315 (4) 140
C10B—H6A1⋯O1Aiii 0.98 2.58 3.542 (4) 169
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2010[Bruker (2010). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812029716/rz2778sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029716/rz2778Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029716/rz2778Isup3.cml

checkCIF report


Comment top

Schiff bases and their metal complexes exhibit unique properties which make them favourable for an array of applications such as catalysis and medicinal chemistry (Kumar et al., 2009). Moreover, Schiff bases have the added advantage of being readily derivatized and their imino nitrogen atoms possess high thermodynamic stability towards various metal centres. In an attempt, to afford a novel rhenium(I) complex containing the Schiff base, C14H16N4O2S, the title compound was unexpectedly isolated. The asymmetric unit consists of the Schiff base molecule and a tricyclic molecule, (Fig. 1) which are planar. The tricyclic molecule has been previously isolated by the oxidative deamination of 5,6-diamino-1,3-dimethylpyrimidine-2,4(1H, 3H)-dione by ammonium perrhenate (Booysen et al., 2008).

In the Schiff base molecule, the ortho-(thiomethyl) phenyl moiety is nearly co-planar with the 6-amino-1,3-dimethylpyrimidine-2,4(1H, 3H)-dione moiety. The largest deviation from the 21-atom mean plane defined by all non-hydrogen atoms of the Schiff base molecule is 0.097 (1) Å exhibited by the primary amine nitrogen atom. The C7—N1A bond length, 1.282 (4) Å, and the C8A—N1A—C7A bond angle, 124.5 (3)°, emphasize the sp2 hybridization of the imino nitrogen atom. An E-configuration is observed for the Schiff base moiety.

The tricyclic molecule consists of three fused rings, a central pyrazine ring and two terminal pyrimidine rings. The largest deviation from planarity is shown by the methyl carbon atom C10B, which is displaced by 0.129 (1) Å from the 22-atom mean plane defined by all non-hydrogen atoms. The bond lengths within the pyrazine ring suggest that they are part of a π-delocalized ring system. Thus the N4B and N5B atoms are sp2-hybridized which is confirmed by the bond angles C5B—N5B—C3B [117.2 (2)°] and C6B—N4B—C4B [115.6 (2)°].

The two molecules exhibit π-π interactions. Each tricyclic molecule is sandwiched between two Schiff base molecules. The distance between the centroid of the pyrazine ring, Cg1, and the centroid of the Schiff base phenyl ring, Cg2, within the aysmmetric unit is 3.517 (1) Å. The distance between Cg1 and Cg2 of a symmetry related molecule is 3.658 (1) Å (Figure 2). The crystal lattice is further stablized by a large number of both classical and non-classical hydrogen bonds. These hydrogen bonds are both inter and inramolecular in nature and ultimately link the Schiff base and tricyclic molecules into an infinite, three-dimensional network. Hydrogen bond lengths and angles are summarized in Table 1. The hydrogen bonding pattern is illustrated in Figure 3.

Related literature top

For the crystal structure of a Schiff base derived from 5,6-diamino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione and picolinaldehyde, see: Booysen et al. (2011a). For the crystal structure of C14H16N4O2S, see: Booysen et al. (2011b). For the crystal structure of C12H12N6O4, see: Booysen et al. (2008). For details of the use of theSchiff base N-(2-aminobenzylidene)-5-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione as a chelating ligand towards rhenium, see: Mayer et al. (2010). For applications of Schiff base ligands, see: Kumar et al.. 2009.

Experimental top

The title compound was prepared from the reaction of [Re(CO5Br] (100 mg, 245 µmol) and 6-amino-1,3-dimethyl-5-[(E)-2-(methylsulfanyl)benzylideneamino]pyrimidine-2,4(1H,3H)-dione (149 mg, 490 µmol) in refluxing toluene (20 cm3) for three hours under nitrogen. X-ray quality yellow crystals were grown from the slow evaporation of the mother liquor.

Refinement top

All non-hydrogen atoms were located in the difference Fourier map and refined anisotropically. The positions of all hydrogen atoms were calculated using the standard riding model of SHELXL97 with C—H(aromatic) distances of 0.93 Å and Uiso = 1.2 Ueq, and C—H(methyl) distances of 0.96 Å and Uiso = 1.5 Ueq. The amine hydrogen atoms were located in the difference Fourier map and allowed to refine isotropically.

Structure description top

Schiff bases and their metal complexes exhibit unique properties which make them favourable for an array of applications such as catalysis and medicinal chemistry (Kumar et al., 2009). Moreover, Schiff bases have the added advantage of being readily derivatized and their imino nitrogen atoms possess high thermodynamic stability towards various metal centres. In an attempt, to afford a novel rhenium(I) complex containing the Schiff base, C14H16N4O2S, the title compound was unexpectedly isolated. The asymmetric unit consists of the Schiff base molecule and a tricyclic molecule, (Fig. 1) which are planar. The tricyclic molecule has been previously isolated by the oxidative deamination of 5,6-diamino-1,3-dimethylpyrimidine-2,4(1H, 3H)-dione by ammonium perrhenate (Booysen et al., 2008).

In the Schiff base molecule, the ortho-(thiomethyl) phenyl moiety is nearly co-planar with the 6-amino-1,3-dimethylpyrimidine-2,4(1H, 3H)-dione moiety. The largest deviation from the 21-atom mean plane defined by all non-hydrogen atoms of the Schiff base molecule is 0.097 (1) Å exhibited by the primary amine nitrogen atom. The C7—N1A bond length, 1.282 (4) Å, and the C8A—N1A—C7A bond angle, 124.5 (3)°, emphasize the sp2 hybridization of the imino nitrogen atom. An E-configuration is observed for the Schiff base moiety.

The tricyclic molecule consists of three fused rings, a central pyrazine ring and two terminal pyrimidine rings. The largest deviation from planarity is shown by the methyl carbon atom C10B, which is displaced by 0.129 (1) Å from the 22-atom mean plane defined by all non-hydrogen atoms. The bond lengths within the pyrazine ring suggest that they are part of a π-delocalized ring system. Thus the N4B and N5B atoms are sp2-hybridized which is confirmed by the bond angles C5B—N5B—C3B [117.2 (2)°] and C6B—N4B—C4B [115.6 (2)°].

The two molecules exhibit π-π interactions. Each tricyclic molecule is sandwiched between two Schiff base molecules. The distance between the centroid of the pyrazine ring, Cg1, and the centroid of the Schiff base phenyl ring, Cg2, within the aysmmetric unit is 3.517 (1) Å. The distance between Cg1 and Cg2 of a symmetry related molecule is 3.658 (1) Å (Figure 2). The crystal lattice is further stablized by a large number of both classical and non-classical hydrogen bonds. These hydrogen bonds are both inter and inramolecular in nature and ultimately link the Schiff base and tricyclic molecules into an infinite, three-dimensional network. Hydrogen bond lengths and angles are summarized in Table 1. The hydrogen bonding pattern is illustrated in Figure 3.

For the crystal structure of a Schiff base derived from 5,6-diamino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione and picolinaldehyde, see: Booysen et al. (2011a). For the crystal structure of C14H16N4O2S, see: Booysen et al. (2011b). For the crystal structure of C12H12N6O4, see: Booysen et al. (2008). For details of the use of theSchiff base N-(2-aminobenzylidene)-5-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione as a chelating ligand towards rhenium, see: Mayer et al. (2010). For applications of Schiff base ligands, see: Kumar et al.. 2009.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT-Plus (Bruker, 2010); data reduction: SAINT-Plus (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids have been rendered at the 50% probability level.
[Figure 2] Fig. 2. The tricyclic molecule sandwiched between two Schiff base molecules. π -π interactions are shown as dashed lines.
[Figure 3] Fig. 3. Hydrogen bonding between the tricyclic molecule and the Schiff base molecule.
6-Amino-1,3-dimethyl-5-[(E)-2- (methylsulfanyl)benzylideneamino]pyrimidine-2,4(1H,3H)-dione– 1,3,7,9-tetramethylpyrimido[5,4-g]pteridine-2,4,6,8-tetrone (1/1) top
Crystal data top
C12H12N6O4·C14H16N4O2SF(000) = 1272
Mr = 608.64Dx = 1.529 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4076 reflections
a = 6.8501 (9) Åθ = 1.6–27.3°
b = 25.594 (4) ŵ = 0.19 mm−1
c = 15.284 (2) ÅT = 100 K
β = 99.315 (5)°Needle, yellow
V = 2644.3 (7) Å30.30 × 0.05 × 0.05 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		5846 independent reflections
Radiation source: fine-focus sealed tube4076 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ω and φ scansθmax = 27.3°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker 2010)		h = −4→8
Tmin = 0.946, Tmax = 0.991k = −32→25
14953 measured reflectionsl = −19→18
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0805P)2 + 2.8029P]
where P = (Fo2 + 2Fc2)/3
5846 reflections(Δ/σ)max = 0.021
403 parametersΔρmax = 0.42 e Å−3
0 restraintsΔρmin = −0.39 e Å−3
Crystal data top
C12H12N6O4·C14H16N4O2SV = 2644.3 (7) Å3
Mr = 608.64Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.8501 (9) ŵ = 0.19 mm−1
b = 25.594 (4) ÅT = 100 K
c = 15.284 (2) Å0.30 × 0.05 × 0.05 mm
β = 99.315 (5)°
Data collection top
Bruker APEXII CCD
diffractometer		5846 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker 2010)		4076 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.991Rint = 0.057
14953 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.171H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.42 e Å−3
5846 reflectionsΔρmin = −0.39 e Å−3
403 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S10.72820 (11)0.31430 (3)0.09858 (5)0.01445 (19)
N1A0.7048 (4)0.19781 (9)0.29893 (16)0.0137 (5)
C6B0.3512 (4)0.38704 (11)0.29375 (18)0.0122 (6)
C10A0.5483 (4)0.04004 (11)0.24893 (18)0.0117 (6)
O1B0.1720 (3)0.16717 (9)0.27878 (15)0.0216 (5)
C9A0.6023 (4)0.12732 (11)0.18728 (19)0.0123 (6)
O2B0.1935 (3)0.26945 (8)0.03637 (13)0.0185 (5)
C2B0.2047 (4)0.26570 (12)0.11659 (19)0.0138 (6)
N3A0.5985 (4)0.06106 (9)0.33332 (15)0.0130 (5)
O3A0.4773 (3)0.51453 (8)0.37187 (14)0.0226 (5)
N2B0.3985 (4)0.42849 (10)0.35067 (15)0.0141 (5)
O4A0.3461 (3)0.45658 (8)0.08667 (13)0.0204 (5)
N1B0.4176 (4)0.48549 (10)0.22915 (16)0.0140 (5)
C12A0.5942 (5)0.02564 (12)0.4084 (2)0.0200 (7)
H2'10.5327−0.00750.38690.030*
H2'20.51740.04160.45020.030*
H2'30.72960.01910.43840.030*
N4A0.5536 (3)0.07345 (9)0.17905 (15)0.0130 (5)
N6B0.1685 (4)0.21905 (10)0.15727 (16)0.0154 (5)
N3B0.2817 (3)0.35639 (10)0.14445 (15)0.0130 (5)
O2A0.5003 (3)−0.00589 (8)0.23777 (13)0.0160 (5)
C12B0.4159 (5)0.42088 (13)0.44709 (19)0.0194 (7)
H8A10.31390.39640.45950.029*
H8A20.39850.45450.47560.029*
H8A30.54700.40670.47040.029*
C13B0.2677 (5)0.24331 (13)0.39999 (19)0.0219 (7)
H5A10.39210.22480.42010.033*
H5A20.15660.22200.41250.033*
H5A30.26840.27670.43130.033*
C13A0.5062 (5)0.05017 (12)0.09037 (18)0.0176 (7)
H1'10.59630.02100.08540.026*
H1'20.52120.07660.04550.026*
H1'30.36950.03740.08100.026*
O1A0.5986 (3)0.15304 (8)0.11890 (13)0.0185 (5)
N4B0.3251 (4)0.34063 (9)0.32905 (15)0.0125 (5)
C5B0.3307 (4)0.39547 (11)0.20163 (18)0.0124 (6)
N2A0.7067 (4)0.12816 (11)0.43183 (17)0.0173 (6)
N5B0.2466 (4)0.25296 (10)0.30381 (15)0.0146 (5)
C11A0.6542 (4)0.11251 (11)0.34771 (18)0.0118 (6)
C3A0.8699 (4)0.38866 (12)0.33665 (19)0.0162 (6)
H30.90550.42280.35790.019*
C7A0.7108 (4)0.23495 (11)0.24313 (18)0.0128 (6)
H70.68040.22800.18140.015*
C5A0.7767 (4)0.32939 (11)0.21317 (18)0.0118 (6)
C8B0.3641 (4)0.44696 (12)0.16650 (19)0.0146 (6)
C7B0.4332 (4)0.47830 (12)0.32141 (19)0.0151 (6)
C1B0.1943 (4)0.20993 (12)0.2492 (2)0.0164 (6)
C8A0.6539 (4)0.14645 (11)0.27595 (18)0.0116 (6)
C2A0.8602 (4)0.34814 (12)0.39644 (19)0.0153 (6)
H40.89050.35440.45840.018*
C6A0.7642 (4)0.28798 (11)0.27399 (18)0.0126 (6)
C4A0.8276 (4)0.37937 (11)0.24528 (19)0.0131 (6)
H20.83360.40730.20490.016*
C1A0.8059 (4)0.29850 (12)0.36480 (19)0.0143 (6)
H50.79680.27110.40580.017*
C3B0.2553 (4)0.30973 (11)0.17811 (18)0.0116 (6)
C4B0.2761 (4)0.30162 (11)0.27104 (18)0.0125 (6)
C11B0.4385 (5)0.53951 (12)0.1995 (2)0.0190 (7)
H9A10.47010.53940.13920.028*
H9A20.54520.55680.23960.028*
H9A30.31420.55840.20000.028*
C10B0.1018 (5)0.17369 (12)0.1007 (2)0.0211 (7)
H6A1−0.03110.16340.11000.032*
H6A20.19340.14450.11630.032*
H6A30.09890.18300.03840.032*
C14A0.7605 (5)0.37598 (12)0.0459 (2)0.0202 (7)
H20A0.66720.40160.06310.030*
H20B0.73580.3715−0.01860.030*
H20C0.89610.38840.06470.030*
H1010.732 (5)0.1605 (14)0.439 (2)0.020 (9)*
H1020.737 (6)0.1055 (16)0.482 (3)0.040 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0197 (4)0.0154 (4)0.0089 (4)−0.0009 (3)0.0042 (3)−0.0001 (3)
N1A0.0140 (13)0.0124 (13)0.0152 (13)−0.0009 (10)0.0035 (9)−0.0011 (10)
C6B0.0082 (13)0.0170 (15)0.0112 (14)0.0029 (11)0.0010 (10)−0.0040 (11)
C10A0.0116 (14)0.0135 (15)0.0106 (14)0.0021 (11)0.0035 (10)0.0014 (11)
O1B0.0240 (12)0.0175 (12)0.0230 (12)0.0009 (9)0.0031 (9)0.0015 (9)
C9A0.0106 (14)0.0120 (15)0.0148 (15)0.0000 (11)0.0039 (10)0.0015 (11)
O2B0.0192 (11)0.0264 (12)0.0095 (10)−0.0005 (9)0.0011 (8)−0.0064 (9)
C2B0.0092 (14)0.0191 (16)0.0130 (15)0.0007 (11)0.0015 (10)−0.0030 (11)
N3A0.0164 (13)0.0147 (13)0.0080 (12)−0.0017 (10)0.0022 (9)0.0020 (9)
O3A0.0314 (13)0.0205 (12)0.0154 (12)−0.0035 (10)0.0022 (9)−0.0066 (9)
N2B0.0186 (13)0.0175 (13)0.0054 (12)0.0016 (10)−0.0005 (9)−0.0038 (9)
O4A0.0287 (13)0.0236 (12)0.0087 (11)−0.0002 (10)0.0024 (9)0.0020 (9)
N1B0.0134 (13)0.0171 (13)0.0116 (13)−0.0026 (10)0.0025 (9)−0.0022 (10)
C12A0.0311 (18)0.0174 (16)0.0118 (15)−0.0057 (13)0.0042 (12)0.0035 (12)
N4A0.0159 (13)0.0142 (13)0.0087 (12)0.0000 (10)0.0008 (9)−0.0007 (9)
N6B0.0156 (13)0.0164 (13)0.0144 (13)−0.0020 (10)0.0031 (9)−0.0062 (10)
N3B0.0108 (12)0.0188 (13)0.0093 (12)0.0014 (10)0.0016 (9)−0.0030 (10)
O2A0.0217 (12)0.0123 (11)0.0137 (11)−0.0012 (9)0.0021 (8)0.0003 (8)
C12B0.0272 (17)0.0241 (17)0.0065 (14)0.0013 (14)0.0013 (12)−0.0031 (12)
C13B0.0320 (19)0.0237 (17)0.0088 (15)0.0002 (14)−0.0002 (12)0.0033 (12)
C13A0.0262 (17)0.0153 (16)0.0099 (15)−0.0023 (13)−0.0010 (12)−0.0026 (12)
O1A0.0265 (12)0.0181 (12)0.0104 (11)−0.0025 (9)0.0016 (9)0.0019 (8)
N4B0.0140 (12)0.0161 (13)0.0072 (12)0.0031 (10)0.0015 (9)−0.0021 (9)
C5B0.0097 (14)0.0194 (16)0.0076 (14)0.0019 (11)0.0000 (10)−0.0028 (11)
N2A0.0289 (15)0.0148 (15)0.0081 (13)−0.0034 (11)0.0021 (10)0.0000 (10)
N5B0.0184 (13)0.0153 (13)0.0095 (12)0.0032 (10)0.0004 (9)−0.0008 (10)
C11A0.0109 (14)0.0122 (14)0.0129 (14)0.0015 (11)0.0043 (10)−0.0006 (11)
C3A0.0167 (15)0.0154 (15)0.0175 (16)−0.0018 (12)0.0053 (12)−0.0036 (12)
C7A0.0130 (14)0.0180 (16)0.0074 (13)0.0006 (12)0.0019 (10)0.0002 (11)
C5A0.0091 (14)0.0148 (15)0.0124 (14)0.0004 (11)0.0043 (10)−0.0007 (11)
C8B0.0122 (14)0.0202 (16)0.0112 (15)0.0028 (12)0.0012 (11)−0.0030 (12)
C7B0.0128 (15)0.0207 (16)0.0114 (15)0.0016 (12)0.0009 (11)−0.0046 (12)
C1B0.0114 (15)0.0189 (17)0.0185 (16)0.0023 (12)0.0014 (11)−0.0025 (12)
C8A0.0135 (14)0.0132 (15)0.0086 (14)0.0017 (11)0.0034 (10)0.0004 (11)
C2A0.0155 (15)0.0185 (16)0.0123 (15)−0.0018 (12)0.0041 (11)−0.0016 (12)
C6A0.0106 (14)0.0139 (15)0.0139 (15)0.0018 (11)0.0041 (11)0.0013 (11)
C4A0.0132 (14)0.0135 (15)0.0129 (14)0.0010 (11)0.0030 (11)0.0028 (11)
C1A0.0132 (14)0.0187 (16)0.0118 (14)0.0001 (12)0.0045 (11)0.0025 (12)
C3B0.0090 (13)0.0178 (16)0.0080 (14)0.0031 (11)0.0016 (10)−0.0033 (11)
C4B0.0093 (13)0.0186 (16)0.0091 (14)0.0054 (11)−0.0001 (10)−0.0026 (11)
C11B0.0205 (16)0.0169 (16)0.0202 (16)−0.0051 (13)0.0054 (12)−0.0008 (13)
C10B0.0227 (17)0.0199 (17)0.0209 (17)−0.0036 (13)0.0043 (13)−0.0103 (13)
C14A0.0303 (18)0.0191 (17)0.0120 (15)0.0030 (13)0.0061 (12)0.0031 (12)
Geometric parameters (Å, º) top
S1—C5A1.772 (3)C13B—N5B1.475 (4)
S1—C14A1.802 (3)C13B—H5A10.9800
N1A—C7A1.282 (4)C13B—H5A20.9800
N1A—C8A1.391 (4)C13B—H5A30.9800
C6B—N4B1.329 (4)C13A—H1'10.9800
C6B—N2B1.377 (4)C13A—H1'20.9800
C6B—C5B1.409 (4)C13A—H1'30.9800
C10A—O2A1.225 (3)N4B—C4B1.341 (4)
C10A—N4A1.373 (4)C5B—C8B1.455 (4)
C10A—N3A1.388 (4)N2A—C11A1.339 (4)
O1B—C1B1.203 (4)N2A—H1010.85 (4)
C9A—O1A1.232 (3)N2A—H1020.96 (4)
C9A—N4A1.419 (4)N5B—C4B1.369 (4)
C9A—C8A1.430 (4)N5B—C1B1.393 (4)
O2B—C2B1.220 (3)C11A—C8A1.399 (4)
C2B—N6B1.387 (4)C3A—C2A1.391 (4)
C2B—C3B1.473 (4)C3A—C4A1.400 (4)
N3A—C11A1.379 (4)C3A—H30.9500
N3A—C12A1.467 (4)C7A—C6A1.464 (4)
O3A—C7B1.213 (3)C7A—H70.9500
N2B—C7B1.384 (4)C5A—C4A1.394 (4)
N2B—C12B1.472 (4)C5A—C6A1.421 (4)
O4A—C8B1.231 (3)C2A—C1A1.388 (4)
N1B—C8B1.382 (4)C2A—H40.9500
N1B—C7B1.409 (4)C6A—C1A1.397 (4)
N1B—C11B1.469 (4)C4A—H20.9500
C12A—H2'10.9800C1A—H50.9500
C12A—H2'20.9800C3B—C4B1.420 (4)
C12A—H2'30.9800C11B—H9A10.9800
N4A—C13A1.468 (3)C11B—H9A20.9800
N6B—C1B1.407 (4)C11B—H9A30.9800
N6B—C10B1.475 (4)C10B—H6A10.9800
N3B—C3B1.324 (4)C10B—H6A20.9800
N3B—C5B1.335 (4)C10B—H6A30.9800
C12B—H8A10.9800C14A—H20A0.9800
C12B—H8A20.9800C14A—H20B0.9800
C12B—H8A30.9800C14A—H20C0.9800
C5A—S1—C14A103.51 (14)C4B—N5B—C13B121.4 (2)
C7A—N1A—C8A124.5 (3)C1B—N5B—C13B116.0 (2)
N4B—C6B—N2B117.7 (2)N2A—C11A—N3A117.6 (3)
N4B—C6B—C5B123.0 (3)N2A—C11A—C8A122.2 (3)
N2B—C6B—C5B119.2 (3)N3A—C11A—C8A120.2 (3)
O2A—C10A—N4A122.0 (3)C2A—C3A—C4A120.3 (3)
O2A—C10A—N3A121.4 (3)C2A—C3A—H3119.9
N4A—C10A—N3A116.6 (2)C4A—C3A—H3119.9
O1A—C9A—N4A118.1 (3)N1A—C7A—C6A120.4 (3)
O1A—C9A—C8A126.1 (3)N1A—C7A—H7119.8
N4A—C9A—C8A115.8 (2)C6A—C7A—H7119.8
O2B—C2B—N6B122.1 (3)C4A—C5A—C6A119.5 (3)
O2B—C2B—C3B123.5 (3)C4A—C5A—S1123.0 (2)
N6B—C2B—C3B114.4 (2)C6A—C5A—S1117.6 (2)
C11A—N3A—C10A122.6 (2)O4A—C8B—N1B121.1 (3)
C11A—N3A—C12A120.4 (2)O4A—C8B—C5B123.4 (3)
C10A—N3A—C12A117.0 (2)N1B—C8B—C5B115.5 (2)
C6B—N2B—C7B122.7 (2)O3A—C7B—N2B122.5 (3)
C6B—N2B—C12B120.2 (2)O3A—C7B—N1B120.5 (3)
C7B—N2B—C12B117.1 (2)N2B—C7B—N1B117.0 (2)
C8B—N1B—C7B124.7 (3)O1B—C1B—N5B122.0 (3)
C8B—N1B—C11B119.1 (2)O1B—C1B—N6B121.5 (3)
C7B—N1B—C11B115.9 (2)N5B—C1B—N6B116.5 (3)
N3A—C12A—H2'1109.5N1A—C8A—C11A114.9 (2)
N3A—C12A—H2'2109.5N1A—C8A—C9A125.2 (2)
H2'1—C12A—H2'2109.5C11A—C8A—C9A120.0 (3)
N3A—C12A—H2'3109.5C1A—C2A—C3A119.5 (3)
H2'1—C12A—H2'3109.5C1A—C2A—H4120.3
H2'2—C12A—H2'3109.5C3A—C2A—H4120.3
C10A—N4A—C9A124.9 (2)C1A—C6A—C5A118.8 (3)
C10A—N4A—C13A115.8 (2)C1A—C6A—C7A119.9 (3)
C9A—N4A—C13A119.3 (2)C5A—C6A—C7A121.3 (2)
C2B—N6B—C1B126.0 (2)C5A—C4A—C3A120.4 (3)
C2B—N6B—C10B118.4 (2)C5A—C4A—H2119.8
C1B—N6B—C10B115.6 (3)C3A—C4A—H2119.8
C3B—N3B—C5B117.2 (2)C2A—C1A—C6A121.5 (3)
N2B—C12B—H8A1109.5C2A—C1A—H5119.3
N2B—C12B—H8A2109.5C6A—C1A—H5119.3
H8A1—C12B—H8A2109.5N3B—C3B—C4B121.5 (3)
N2B—C12B—H8A3109.5N3B—C3B—C2B118.4 (2)
H8A1—C12B—H8A3109.5C4B—C3B—C2B120.1 (3)
H8A2—C12B—H8A3109.5N4B—C4B—N5B118.1 (2)
N5B—C13B—H5A1109.5N4B—C4B—C3B121.8 (3)
N5B—C13B—H5A2109.5N5B—C4B—C3B120.1 (3)
H5A1—C13B—H5A2109.5N1B—C11B—H9A1109.5
N5B—C13B—H5A3109.5N1B—C11B—H9A2109.5
H5A1—C13B—H5A3109.5H9A1—C11B—H9A2109.5
H5A2—C13B—H5A3109.5N1B—C11B—H9A3109.5
N4A—C13A—H1'1109.5H9A1—C11B—H9A3109.5
N4A—C13A—H1'2109.5H9A2—C11B—H9A3109.5
H1'1—C13A—H1'2109.5N6B—C10B—H6A1109.5
N4A—C13A—H1'3109.5N6B—C10B—H6A2109.5
H1'1—C13A—H1'3109.5H6A1—C10B—H6A2109.5
H1'2—C13A—H1'3109.5N6B—C10B—H6A3109.5
C6B—N4B—C4B115.6 (2)H6A1—C10B—H6A3109.5
N3B—C5B—C6B120.9 (3)H6A2—C10B—H6A3109.5
N3B—C5B—C8B118.4 (2)S1—C14A—H20A109.5
C6B—C5B—C8B120.8 (3)S1—C14A—H20B109.5
C11A—N2A—H101116 (2)H20A—C14A—H20B109.5
C11A—N2A—H102125 (2)S1—C14A—H20C109.5
H101—N2A—H102118 (3)H20A—C14A—H20C109.5
C4B—N5B—C1B122.6 (2)H20B—C14A—H20C109.5
O2A—C10A—N3A—C11A179.6 (3)C8B—N1B—C7B—N2B2.3 (4)
N4A—C10A—N3A—C11A−1.0 (4)C11B—N1B—C7B—N2B175.0 (2)
O2A—C10A—N3A—C12A0.8 (4)C4B—N5B—C1B—O1B178.7 (3)
N4A—C10A—N3A—C12A−179.7 (3)C13B—N5B—C1B—O1B−1.7 (4)
N4B—C6B—N2B—C7B178.6 (3)C4B—N5B—C1B—N6B−1.3 (4)
C5B—C6B—N2B—C7B−2.0 (4)C13B—N5B—C1B—N6B178.3 (3)
N4B—C6B—N2B—C12B−0.9 (4)C2B—N6B—C1B—O1B−174.9 (3)
C5B—C6B—N2B—C12B178.5 (3)C10B—N6B—C1B—O1B3.4 (4)
O2A—C10A—N4A—C9A178.1 (3)C2B—N6B—C1B—N5B5.1 (4)
N3A—C10A—N4A—C9A−1.3 (4)C10B—N6B—C1B—N5B−176.6 (2)
O2A—C10A—N4A—C13A−2.4 (4)C7A—N1A—C8A—C11A−179.1 (3)
N3A—C10A—N4A—C13A178.1 (2)C7A—N1A—C8A—C9A0.5 (5)
O1A—C9A—N4A—C10A−178.9 (3)N2A—C11A—C8A—N1A−2.3 (4)
C8A—C9A—N4A—C10A1.7 (4)N3A—C11A—C8A—N1A177.4 (2)
O1A—C9A—N4A—C13A1.6 (4)N2A—C11A—C8A—C9A178.1 (3)
C8A—C9A—N4A—C13A−177.7 (2)N3A—C11A—C8A—C9A−2.2 (4)
O2B—C2B—N6B—C1B174.2 (3)O1A—C9A—C8A—N1A1.2 (5)
C3B—C2B—N6B—C1B−6.4 (4)N4A—C9A—C8A—N1A−179.5 (3)
O2B—C2B—N6B—C10B−4.1 (4)O1A—C9A—C8A—C11A−179.2 (3)
C3B—C2B—N6B—C10B175.4 (2)N4A—C9A—C8A—C11A0.1 (4)
N2B—C6B—N4B—C4B179.0 (2)C4A—C3A—C2A—C1A−0.8 (4)
C5B—C6B—N4B—C4B−0.4 (4)C4A—C5A—C6A—C1A−0.8 (4)
C3B—N3B—C5B—C6B−0.6 (4)S1—C5A—C6A—C1A178.6 (2)
C3B—N3B—C5B—C8B178.9 (3)C4A—C5A—C6A—C7A179.9 (3)
N4B—C6B—C5B—N3B0.5 (4)S1—C5A—C6A—C7A−0.8 (4)
N2B—C6B—C5B—N3B−178.9 (3)N1A—C7A—C6A—C1A−1.0 (4)
N4B—C6B—C5B—C8B−179.0 (3)N1A—C7A—C6A—C5A178.3 (3)
N2B—C6B—C5B—C8B1.6 (4)C6A—C5A—C4A—C3A1.2 (4)
C10A—N3A—C11A—N2A−177.6 (3)S1—C5A—C4A—C3A−178.1 (2)
C12A—N3A—C11A—N2A1.1 (4)C2A—C3A—C4A—C5A−0.5 (4)
C10A—N3A—C11A—C8A2.7 (4)C3A—C2A—C1A—C6A1.2 (4)
C12A—N3A—C11A—C8A−178.6 (3)C5A—C6A—C1A—C2A−0.5 (4)
C8A—N1A—C7A—C6A179.3 (3)C7A—C6A—C1A—C2A178.9 (3)
C14A—S1—C5A—C4A−0.3 (3)C5B—N3B—C3B—C4B0.6 (4)
C14A—S1—C5A—C6A−179.7 (2)C5B—N3B—C3B—C2B−178.9 (2)
C7B—N1B—C8B—O4A177.1 (3)O2B—C2B—C3B—N3B3.0 (4)
C11B—N1B—C8B—O4A4.6 (4)N6B—C2B—C3B—N3B−176.5 (2)
C7B—N1B—C8B—C5B−2.6 (4)O2B—C2B—C3B—C4B−176.5 (3)
C11B—N1B—C8B—C5B−175.1 (3)N6B—C2B—C3B—C4B4.1 (4)
N3B—C5B—C8B—O4A1.4 (4)C6B—N4B—C4B—N5B−179.7 (2)
C6B—C5B—C8B—O4A−179.1 (3)C6B—N4B—C4B—C3B0.4 (4)
N3B—C5B—C8B—N1B−178.9 (2)C1B—N5B—C4B—N4B179.6 (3)
C6B—C5B—C8B—N1B0.6 (4)C13B—N5B—C4B—N4B0.0 (4)
C6B—N2B—C7B—O3A−179.0 (3)C1B—N5B—C4B—C3B−0.5 (4)
C12B—N2B—C7B—O3A0.4 (4)C13B—N5B—C4B—C3B179.9 (3)
C6B—N2B—C7B—N1B0.2 (4)N3B—C3B—C4B—N4B−0.5 (4)
C12B—N2B—C7B—N1B179.6 (2)C2B—C3B—C4B—N4B178.9 (2)
C8B—N1B—C7B—O3A−178.5 (3)N3B—C3B—C4B—N5B179.6 (3)
C11B—N1B—C7B—O3A−5.8 (4)C2B—C3B—C4B—N5B−0.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H101···N1A0.85 (4)2.32 (3)2.701 (4)107 (2)
N2A—H101···O2Bi0.85 (4)2.37 (3)3.078 (3)141 (3)
N2A—H102···O4Ai0.96 (4)2.29 (4)3.238 (3)169 (3)
C12A—H2′1···O2A0.982.252.706 (4)107
C4A—H2···O2Aii0.952.583.159 (4)119
C3A—H3···O2Aii0.952.493.114 (4)123
C12A—H2′3···O4Ai0.982.363.014 (4)123
C1A—H5···O2Bi0.952.453.339 (4)155
C12B—H8A2···O3A0.982.332.720 (4)103
C7A—H7···S10.952.593.017 (3)108
C7A—H7···O1A0.952.182.849 (3)127
C13B—H5A1···O2Bi0.982.503.315 (4)140
C13B—H5A3···N4B0.982.342.770 (4)106
C13A—H1′2···O1A0.982.282.726 (4)107
C11B—H9A1···O4A0.982.372.744 (4)102
C10B—H6A3···O2B0.982.312.751 (4)107
C10B—H6A1···O1Aiii0.982.583.542 (4)169
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC12H12N6O4·C14H16N4O2S
Mr608.64
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)6.8501 (9), 25.594 (4), 15.284 (2)
β (°) 99.315 (5)
V (Å3)2644.3 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.19
Crystal size (mm)0.30 × 0.05 × 0.05
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker 2010)
Tmin, Tmax0.946, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections		14953, 5846, 4076
Rint0.057
(sin θ/λ)max (Å−1)0.646
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.171, 1.01
No. of reflections5846
No. of parameters403
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.42, −0.39

Computer programs: APEX2 (Bruker, 2010), SAINT-Plus (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H101···N1A0.85 (4)2.32 (3)2.701 (4)107 (2)
N2A—H101···O2Bi0.85 (4)2.37 (3)3.078 (3)141 (3)
N2A—H102···O4Ai0.96 (4)2.29 (4)3.238 (3)169 (3)
C4A—H2···O2Aii0.952.583.159 (4)119
C3A—H3···O2Aii0.952.493.114 (4)123
C12A—H2'3···O4Ai0.982.363.014 (4)123
C1A—H5···O2Bi0.952.453.339 (4)155
C7A—H7···S10.952.593.017 (3)108
C7A—H7···O1A0.952.182.849 (3)127
C13B—H5A1···O2Bi0.982.503.315 (4)140
C10B—H6A1···O1Aiii0.982.583.542 (4)169
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x−1, y, z.
 

Acknowledgements

We would like to thank University of KwaZulu-Natal and the National Research Foundation of South Africa for funding.

References

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ISSN: 2056-9890
Volume 68| Part 8| August 2012| Pages o2334-o2335
https://doi.org/10.1107/S1600536812029716
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