Literature DB >> 23476209

6-Methyl-1,3,5-triazine-2,4-diamine butane-1,4-diol monosolvate.

Rajni M Bhardwaj¹, Iain Oswald, Alastair J Florence.

Abstract

The title co-crystal, C4H7N5·C4H10O2, crystallizes with one mol-ecule of n class="Chemical">6-methyl-1,3,5-triazine-2,4-diamine (DMT) and one mol-ecule of butane-1,4-diol in the asymmetric unit. The DMT mol-ecules form ribbons involving centrosymmetric R2(2)(8) dimer motifs between DMT mol-ecules along the c-axis direction. These ribbons are further hydrogen bonded to each other through butane-1,4-diol, forming sheets parallel to (121).

Entities: Chemical Disease Species

Year: 2012 PMID： 23476209 PMCID： PMC3588973 DOI： 10.1107/S1600536812044480

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to DMT and related structural studies, see: Šebenik et al. (1989 ▶); Kaczmarek et al. (2008 ▶); n class="Chemical">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

C4H7N5·C4H10O2 M = 215.27 Triclinic, a = 5.8755 (3) Å b = 9.0515 (5) Å c = 10.7607 (5) Å α = 87.911 (3)° β = 74.346 (3)° γ = 83.550 (3)° V = 547.55 (5) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 123 K 0.50 × 0.05 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.637, T max = 0.745 7713 measured reflections 1911 independent reflections 1288 reflections with I > 2σ(I) R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.093 S = 1.00 1911 reflections 155 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.20 e Å−3 Δρmin = −0.22 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: 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) ▶. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044480/bh2459sup1.cif Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812044480/bh2459Isup2.mol Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044480/bh2459Isup3.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812044480/bh2459Isup4.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₄H₇N₅·C₄H₁₀O₂	Z = 2
M_r = 215.27	F(000) = 232
Triclinic, P1	D_x = 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	R_int = 0.045
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −6→6
T_min = 0.637, T_max = 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(F_o²) + (0.0401P)² + 0.1476P] where P = (F_o² + 2F_c²)/3
1911 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³
0 constraints

	x	y	z	U_iso*/U_eq
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···N2^iv	0.85 (2)	2.19 (2)	3.037 (2)	178 (2)
N5—H9N···O1^v	0.88 (2)	2.069 (19)	2.909 (2)	160.1 (18)
N5—H10N···N3^v	0.87 (2)	2.14 (2)	3.008 (3)	179 (2)

Table 1

Hydrogen-bond geometry (Å, °)

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⋯N2^iv	0.85 (2)	2.19 (2)	3.037 (2)	178 (2)
N5—H9N⋯O1^v	0.88 (2)	2.069 (19)	2.909 (2)	160.1 (18)
N5—H10N⋯N3^v	0.87 (2)	2.14 (2)	3.008 (3)	179 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

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