organic compounds
6-Methyl-1,3,5-triazine-2,4-diamine butane-1,4-diol monosolvate
aStrathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, Scotland
*Correspondence e-mail: alastair.florence@strath.ac.uk
The title 4H7N5·C4H10O2, crystallizes with one molecule of 6-methyl-1,3,5-triazine-2,4-diamine (DMT) and one molecule of butane-1,4-diol in the The DMT molecules form ribbons involving centrosymmetric R22(8) dimer motifs between DMT molecules along the c-axis direction. These ribbons are further hydrogen bonded to each other through butane-1,4-diol, forming sheets parallel to (121).
CRelated literature
For background to DMT and related structural studies, see: Šebenik et al. (1989); Kaczmarek et al. (2008); Portalone (2008); Xiao (2008); Fan et al. (2009); Qian & Huang (2010); Thanigaimani et al. (2010); Perpétuo & Janczak (2007); Portalone & Colapietro (2007); Delori et al. (2008). For details of experimental methods used, see: Florence et al. (2003). For ring-motif nomenclature, see: Etter (1990).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: enCIFer (Allen et al., 2004) and WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536812044480/bh2459sup1.cif
contains datablocks I, global. DOI:Supporting information file. DOI: 10.1107/S1600536812044480/bh2459Isup2.mol
Structure factors: contains datablock I. DOI: 10.1107/S1600536812044480/bh2459Isup3.hkl
Supporting information file. DOI: 10.1107/S1600536812044480/bh2459Isup4.cml
A single needle shape crystal was grown from the
of DMT in butane-1,4-diol by isothermal solvent evaporation at 298 K.The positions of the N-bound H atoms were refined freely. All other H atoms were placed in calculated positions and refined in riding modes with X—H = 0.98 or 0.99 or 0.84 Å for the CH3, CH2 and OH groups, respectively. The Uiso(H) values were set to 1.5 or 1.2 times Ueq of their parent C atoms for the CH3 and CH2 groups, respectively. The Uiso(H) values were set to 1.5 times Ueq of their parent O atoms for the OH groups.
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: enCIFer (Allen et al., 2004) and WinGX (Farrugia, 1999).Fig. 1. The asymmetric unit of 2,4-diamino-6-methyl-1,3,5-triazine (DMT), butane-1,4-diol solvate. Displacement ellipsoids are drawn at 50% probability level. | |
Fig. 2. DMT molecules form ribbons through R22(8) dimer, ribbons are connected via H-bonding (shown in cyan dotted line) interactions mediated by butane-1,4-diol, thus give rise to sheet structure. C, N and H atoms are shown in black, blue and tan colour respectively. Other H atoms are omitted for clarity. | |
Fig. 3. 3-D Layered structure formed by sheets connected through H-bonding (cyan dotted line) mediated by butane-1,4-diol. C, N and H atoms are shown in grey, blue and white colour respectively. Other H atoms are omitted for clarity. |
C4H7N5·C4H10O2 | Z = 2 |
Mr = 215.27 | F(000) = 232 |
Triclinic, P1 | Dx = 1.306 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8755 (3) Å | Cell parameters from 1602 reflections |
b = 9.0515 (5) Å | θ = 2.3–24.6° |
c = 10.7607 (5) Å | µ = 0.10 mm−1 |
α = 87.911 (3)° | T = 123 K |
β = 74.346 (3)° | Needle, colourless |
γ = 83.550 (3)° | 0.50 × 0.05 × 0.04 mm |
V = 547.55 (5) Å3 |
Bruker APEXII CCD diffractometer | 1911 independent reflections |
Radiation source: fine-focus sealed tube | 1288 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −6→6 |
Tmin = 0.637, Tmax = 0.745 | k = −10→10 |
7713 measured reflections | l = −12→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0401P)2 + 0.1476P] where P = (Fo2 + 2Fc2)/3 |
1911 reflections | (Δ/σ)max < 0.001 |
155 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
0 constraints |
C4H7N5·C4H10O2 | γ = 83.550 (3)° |
Mr = 215.27 | V = 547.55 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.8755 (3) Å | Mo Kα radiation |
b = 9.0515 (5) Å | µ = 0.10 mm−1 |
c = 10.7607 (5) Å | T = 123 K |
α = 87.911 (3)° | 0.50 × 0.05 × 0.04 mm |
β = 74.346 (3)° |
Bruker APEXII CCD diffractometer | 1911 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 1288 reflections with I > 2σ(I) |
Tmin = 0.637, Tmax = 0.745 | Rint = 0.045 |
7713 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.20 e Å−3 |
1911 reflections | Δρmin = −0.22 e Å−3 |
155 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5923 (3) | 0.3881 (2) | 0.16893 (18) | 0.0160 (5) | |
C2 | 0.2419 (3) | 0.4825 (2) | 0.30267 (18) | 0.0163 (5) | |
C3 | 0.5020 (3) | 0.3277 (2) | 0.38201 (19) | 0.0174 (5) | |
C4 | 0.5670 (4) | 0.2448 (2) | 0.49230 (19) | 0.0243 (5) | |
H4A | 0.4317 | 0.2559 | 0.5692 | 0.036* | |
H4B | 0.7035 | 0.2850 | 0.5095 | 0.036* | |
H4C | 0.6083 | 0.1393 | 0.4705 | 0.036* | |
C5 | 0.3181 (3) | 0.1867 (2) | 0.9133 (2) | 0.0207 (5) | |
H5A | 0.2639 | 0.1078 | 0.9771 | 0.025* | |
H5B | 0.3114 | 0.2788 | 0.9615 | 0.025* | |
C6 | 0.5730 (3) | 0.1418 (2) | 0.83897 (19) | 0.0182 (5) | |
H6A | 0.6744 | 0.1373 | 0.8993 | 0.022* | |
H6B | 0.6254 | 0.2195 | 0.7737 | 0.022* | |
C7 | 0.6115 (3) | −0.0072 (2) | 0.77120 (19) | 0.0191 (5) | |
H7A | 0.5611 | −0.0855 | 0.8363 | 0.023* | |
H7B | 0.5099 | −0.0033 | 0.7110 | 0.023* | |
C8 | 0.8673 (3) | −0.0489 (2) | 0.69683 (19) | 0.0220 (5) | |
H8A | 0.8820 | −0.1465 | 0.6551 | 0.026* | |
H8B | 0.9165 | 0.0260 | 0.6282 | 0.026* | |
N1 | 0.6600 (3) | 0.31119 (18) | 0.26599 (15) | 0.0175 (4) | |
N2 | 0.3851 (3) | 0.47401 (18) | 0.18167 (15) | 0.0162 (4) | |
N3 | 0.2928 (3) | 0.41094 (18) | 0.40710 (15) | 0.0174 (4) | |
N4 | 0.7434 (3) | 0.3769 (2) | 0.05127 (17) | 0.0221 (4) | |
N5 | 0.0347 (3) | 0.5670 (2) | 0.32441 (19) | 0.0201 (4) | |
O1 | 0.1589 (2) | 0.21134 (16) | 0.83288 (14) | 0.0238 (4) | |
H1 | 0.1221 | 0.1293 | 0.8146 | 0.036* | |
O2 | 1.0196 (2) | −0.05639 (16) | 0.78135 (13) | 0.0229 (4) | |
H2 | 1.1154 | −0.1339 | 0.7660 | 0.034* | |
H7N | 0.883 (4) | 0.316 (3) | 0.040 (2) | 0.037 (7)* | |
H8N | 0.704 (4) | 0.418 (2) | −0.013 (2) | 0.028 (7)* | |
H9N | −0.008 (3) | 0.618 (2) | 0.262 (2) | 0.019 (6)* | |
H10N | −0.059 (4) | 0.572 (2) | 0.402 (2) | 0.026 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0178 (11) | 0.0139 (11) | 0.0162 (11) | −0.0025 (9) | −0.0042 (9) | 0.0004 (9) |
C2 | 0.0158 (11) | 0.0155 (11) | 0.0169 (11) | −0.0015 (9) | −0.0036 (9) | 0.0005 (9) |
C3 | 0.0192 (12) | 0.0152 (11) | 0.0180 (11) | 0.0017 (9) | −0.0069 (9) | −0.0010 (9) |
C4 | 0.0269 (12) | 0.0266 (13) | 0.0167 (11) | 0.0075 (10) | −0.0055 (10) | 0.0007 (9) |
C5 | 0.0165 (11) | 0.0232 (13) | 0.0221 (11) | 0.0028 (9) | −0.0062 (9) | −0.0016 (9) |
C6 | 0.0144 (11) | 0.0194 (12) | 0.0210 (11) | −0.0004 (9) | −0.0055 (9) | −0.0001 (9) |
C7 | 0.0166 (11) | 0.0200 (12) | 0.0212 (11) | −0.0005 (9) | −0.0067 (9) | 0.0007 (9) |
C8 | 0.0202 (12) | 0.0240 (13) | 0.0230 (11) | 0.0021 (9) | −0.0088 (10) | −0.0032 (9) |
N1 | 0.0176 (9) | 0.0180 (10) | 0.0151 (9) | 0.0024 (7) | −0.0031 (8) | −0.0012 (7) |
N2 | 0.0151 (9) | 0.0164 (9) | 0.0148 (9) | 0.0024 (7) | −0.0016 (7) | 0.0008 (7) |
N3 | 0.0184 (9) | 0.0175 (10) | 0.0145 (9) | 0.0025 (7) | −0.0033 (7) | 0.0023 (7) |
N4 | 0.0184 (11) | 0.0272 (11) | 0.0152 (10) | 0.0082 (9) | 0.0004 (9) | 0.0015 (8) |
N5 | 0.0172 (10) | 0.0258 (11) | 0.0120 (10) | 0.0071 (8) | 0.0005 (9) | 0.0047 (8) |
O1 | 0.0201 (8) | 0.0202 (8) | 0.0340 (9) | 0.0013 (7) | −0.0139 (7) | 0.0009 (7) |
O2 | 0.0171 (8) | 0.0223 (9) | 0.0299 (9) | 0.0073 (6) | −0.0102 (7) | −0.0055 (7) |
C1—N4 | 1.336 (2) | C6—C7 | 1.522 (3) |
C1—N2 | 1.345 (2) | C6—H6A | 0.9900 |
C1—N1 | 1.357 (2) | C6—H6B | 0.9900 |
C2—N5 | 1.331 (3) | C7—C8 | 1.512 (3) |
C2—N2 | 1.346 (2) | C7—H7A | 0.9900 |
C2—N3 | 1.362 (2) | C7—H7B | 0.9900 |
C3—N3 | 1.334 (2) | C8—O2 | 1.434 (2) |
C3—N1 | 1.342 (2) | C8—H8A | 0.9900 |
C3—C4 | 1.494 (3) | C8—H8B | 0.9900 |
C4—H4A | 0.9800 | N4—H7N | 0.92 (2) |
C4—H4B | 0.9800 | N4—H8N | 0.85 (2) |
C4—H4C | 0.9800 | N5—H9N | 0.87 (2) |
C5—O1 | 1.431 (2) | N5—H10N | 0.87 (2) |
C5—C6 | 1.512 (3) | O1—H1 | 0.8400 |
C5—H5A | 0.9900 | O2—H2 | 0.8400 |
C5—H5B | 0.9900 | ||
N4—C1—N2 | 117.48 (18) | C7—C6—H6B | 108.7 |
N4—C1—N1 | 117.24 (18) | H6A—C6—H6B | 107.6 |
N2—C1—N1 | 125.28 (18) | C8—C7—C6 | 113.03 (17) |
N5—C2—N2 | 118.72 (19) | C8—C7—H7A | 109.0 |
N5—C2—N3 | 116.41 (18) | C6—C7—H7A | 109.0 |
N2—C2—N3 | 124.86 (18) | C8—C7—H7B | 109.0 |
N3—C3—N1 | 125.76 (18) | C6—C7—H7B | 109.0 |
N3—C3—C4 | 117.45 (18) | H7A—C7—H7B | 107.8 |
N1—C3—C4 | 116.79 (17) | O2—C8—C7 | 110.49 (16) |
C3—C4—H4A | 109.5 | O2—C8—H8A | 109.6 |
C3—C4—H4B | 109.5 | C7—C8—H8A | 109.6 |
H4A—C4—H4B | 109.5 | O2—C8—H8B | 109.6 |
C3—C4—H4C | 109.5 | C7—C8—H8B | 109.6 |
H4A—C4—H4C | 109.5 | H8A—C8—H8B | 108.1 |
H4B—C4—H4C | 109.5 | C3—N1—C1 | 114.53 (16) |
O1—C5—C6 | 113.42 (16) | C1—N2—C2 | 114.71 (17) |
O1—C5—H5A | 108.9 | C3—N3—C2 | 114.85 (17) |
C6—C5—H5A | 108.9 | C1—N4—H7N | 118.7 (14) |
O1—C5—H5B | 108.9 | C1—N4—H8N | 120.1 (15) |
C6—C5—H5B | 108.9 | H7N—N4—H8N | 121 (2) |
H5A—C5—H5B | 107.7 | C2—N5—H9N | 121.4 (13) |
C5—C6—C7 | 114.11 (17) | C2—N5—H10N | 119.2 (14) |
C5—C6—H6A | 108.7 | H9N—N5—H10N | 119.4 (19) |
C7—C6—H6A | 108.7 | C5—O1—H1 | 109.5 |
C5—C6—H6B | 108.7 | C8—O2—H2 | 109.5 |
O1—C5—C6—C7 | −64.5 (2) | N1—C1—N2—C2 | 1.1 (3) |
C5—C6—C7—C8 | 179.55 (17) | N5—C2—N2—C1 | 178.99 (18) |
C6—C7—C8—O2 | 59.0 (2) | N3—C2—N2—C1 | −0.6 (3) |
N3—C3—N1—C1 | −0.1 (3) | N1—C3—N3—C2 | 0.5 (3) |
C4—C3—N1—C1 | 179.68 (18) | C4—C3—N3—C2 | −179.23 (18) |
N4—C1—N1—C3 | 179.49 (18) | N5—C2—N3—C3 | −179.76 (18) |
N2—C1—N1—C3 | −0.8 (3) | N2—C2—N3—C3 | −0.1 (3) |
N4—C1—N2—C2 | −179.17 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.92 | 2.764 (2) | 176 |
O2—H2···N1ii | 0.84 | 1.94 | 2.777 (2) | 178 |
N4—H7N···O1iii | 0.92 (3) | 2.52 (2) | 3.173 (2) | 128.5 (7) |
N4—H8N···N2iv | 0.85 (2) | 2.19 (2) | 3.037 (2) | 178 (2) |
N5—H9N···O1v | 0.88 (2) | 2.069 (19) | 2.909 (2) | 160.1 (18) |
N5—H10N···N3v | 0.87 (2) | 2.14 (2) | 3.008 (3) | 179 (2) |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+1; (iii) x+1, y, z−1; (iv) −x+1, −y+1, −z; (v) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C4H7N5·C4H10O2 |
Mr | 215.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 123 |
a, b, c (Å) | 5.8755 (3), 9.0515 (5), 10.7607 (5) |
α, β, γ (°) | 87.911 (3), 74.346 (3), 83.550 (3) |
V (Å3) | 547.55 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.50 × 0.05 × 0.04 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.637, 0.745 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7713, 1911, 1288 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.093, 1.00 |
No. of reflections | 1911 |
No. of parameters | 155 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.22 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008) and ORTEP-3 (Farrugia, 1997), enCIFer (Allen et al., 2004) and WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.92 | 2.764 (2) | 176 |
O2—H2···N1ii | 0.84 | 1.94 | 2.777 (2) | 178 |
N4—H7N···O1iii | 0.92 (3) | 2.52 (2) | 3.173 (2) | 128.5 (7) |
N4—H8N···N2iv | 0.85 (2) | 2.19 (2) | 3.037 (2) | 178 (2) |
N5—H9N···O1v | 0.88 (2) | 2.069 (19) | 2.909 (2) | 160.1 (18) |
N5—H10N···N3v | 0.87 (2) | 2.14 (2) | 3.008 (3) | 179 (2) |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+1; (iii) x+1, y, z−1; (iv) −x+1, −y+1, −z; (v) −x, −y+1, −z+1. |
Acknowledgements
RMB thanks the Commonwealth Scholarship Commission for providing a scholarship.
References
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2,4-diamino-6-methyl-1,3,5-triazine (DMT, acetoguanamine, Fig. 1) is used as an intermediate for pharmaceutical and resin synthesis (Šebenik et al., 1989). The crystal structures of the methanol, ethanol, DMF solvates and trifluoroacetate, phthalate, nitrate and chloride salts as well as of various complexes with aliphatic dicarboxylic acids have been reported in the literature (Kaczmarek et al., 2008; Portalone, 2008; Xiao, 2008; Fan et al., 2009; Qian & Huang, 2010; Thanigaimani et al., 2010; Portalone & Colapietro, 2007; Perpétuo & Janczak, 2007; Delori et al., 2008). The sample of DMT butane-1,4-diol solvate was isolated during an experimental physical form screen. The sample was identified as a novel form using multi-sample foil transmission X-ray powder diffraction analysis (Florence et al., 2003). A suitable sample for single-crystal X-ray diffraction analysis was obtained from slow evaporation of saturated butane-1,4-diol solution at room temperature. The title compound crystallizes in space group P1, with one molecule of DMT and one molecule of butane-1,4-diol in the asymmetric unit. Each DMT molecule forms two hydrogen-bonded dimers via an R22(8) motif (Etter, 1990) that extends to form a ribbon structure along the c-direction (Fig. 2). The hydrogen bonded DMT ribbons connect to adjacent ribbons through the solvent molecule, butane-1,4-diol, thus forming a second R32(8) ring motif (Fig. 2).These solvent separated ribbon structures extended to form sheets parallel to (121) plane, and are connected through hydrogen bond interactions via the hydroxyl groups. Solvent hydroxyl group also donates a hydrogen bond to the solvent in adjacent sheet, creating a three-dimensional layered structure (Fig. 3).