2,4-Diamino-6-methyl-1,3,5-triazine methanol solvate.

The crystal structure of the title compound, C(4)H(7)N(5)·CH(4)O, is determined by an extensive network of hydrogen bonding. A sequence of centrosymmetric dimeric associations, formed by two different N-H(amino)⋯N(ring) hydrogen bonds, connects the triazine rings into a planar mol-ecular tape. The methanol solvent mol-ecules act as di-acceptors and mono-donors of hydrogen bonds and inter-link, almost perpendicularly, the hydrogen-bonded tapes into a three-dimensional structure.

Related literature

For related literature, see: Allen (2002 ▶); Radecka-Paryzek et al. (2005 ▶); Šebenik et al. (1989 ▶); Tashiro & Oiwa (1981 ▶).

Experimental

Crystal data

C4H7N5·CH4O

M = 157.19

Monoclinic,

a = 21.024 (5) Å

b = 5.4726 (10) Å

c = 14.198 (3) Å

β = 95.66 (2)°

V = 1625.6 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 295 (2) K

0.4 × 0.2 × 0.2 mm

Data collection

Kuma KM4 CCD diffractometer

Absorption correction: none

5226 measured reflections

1737 independent reflections

1191 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.146

S = 1.07

1737 reflections

122 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706607X/rz2183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706607X/rz2183Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C4H7N5·CH4O	F000 = 672
Mr = 157.19	Dx = 1.285 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2082 reflections
a = 21.024 (5) Å	θ = 4–22º
b = 5.4726 (10) Å	µ = 0.10 mm−1
c = 14.198 (3) Å	T = 295 (2) K
β = 95.66 (2)º	Block, colourless
V = 1625.6 (6) Å3	0.4 × 0.2 × 0.2 mm
Z = 8

Kuma KM-4-CCD four-circle diffractometer	1737 independent reflections
Radiation source: fine-focus sealed tube	1191 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
Detector resolution: 8.1929 pixels mm-1	θmax = 27.0º
T = 295(1) K	θmin = 2.9º
ω scans	h = −26→26
Absorption correction: none	k = −4→6
5226 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.146	w = 1/[σ2(Fo2) + (0.0834P)2 + 0.3526P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1737 reflections	Δρmax = 0.17 e Å−3
122 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
N1	0.19697 (6)	1.0111 (2)	0.94292 (10)	0.0405 (4)
C2	0.14975 (8)	1.1070 (3)	0.99110 (11)	0.0375 (4)
N2	0.16650 (8)	1.2910 (3)	1.04951 (12)	0.0491 (4)
H2B	0.1372 (12)	1.360 (4)	1.0792 (17)	0.069 (7)*
H2A	0.2049 (11)	1.346 (4)	1.0518 (15)	0.056 (6)*
N3	0.08942 (6)	1.0268 (3)	0.98441 (10)	0.0410 (4)
C4	0.07625 (8)	0.8402 (3)	0.92379 (12)	0.0400 (4)
N4	0.01687 (8)	0.7548 (3)	0.91381 (14)	0.0576 (5)
H4B	0.0074 (11)	0.634 (4)	0.8728 (16)	0.065 (7)*
H4A	−0.0141 (11)	0.813 (4)	0.9441 (16)	0.055 (6)*
N5	0.11934 (6)	0.7355 (3)	0.87109 (10)	0.0412 (4)
C6	0.17841 (8)	0.8266 (3)	0.88561 (12)	0.0388 (4)
C61	0.22793 (9)	0.7086 (4)	0.83245 (15)	0.0521 (5)
H61A	0.2682	0.7898	0.8472	0.068*
H61B	0.2154	0.7205	0.7657	0.068*
H61C	0.2321	0.5397	0.8502	0.068*
O1S	0.08620 (7)	0.4874 (2)	0.69953 (10)	0.0574 (4)
H1S	0.0976 (14)	0.579 (6)	0.756 (3)	0.113 (11)*
C1S	0.08937 (12)	0.2368 (4)	0.71909 (17)	0.0707 (7)
H1S1	0.1329	0.1916	0.7380	0.092*
H1S2	0.0739	0.1469	0.6634	0.092*
H1S3	0.0635	0.2000	0.7693	0.092*

	U11	U22	U33	U12	U13	U23
N1	0.0315 (7)	0.0499 (8)	0.0406 (8)	−0.0021 (6)	0.0066 (6)	−0.0054 (6)
C2	0.0315 (8)	0.0475 (9)	0.0331 (8)	−0.0026 (7)	0.0021 (6)	−0.0012 (7)
N2	0.0350 (8)	0.0597 (10)	0.0532 (10)	−0.0065 (7)	0.0078 (7)	−0.0180 (8)
N3	0.0327 (8)	0.0499 (8)	0.0412 (8)	−0.0050 (6)	0.0078 (6)	−0.0053 (6)
C4	0.0344 (9)	0.0465 (9)	0.0397 (9)	−0.0035 (7)	0.0056 (7)	−0.0003 (7)
N4	0.0382 (9)	0.0674 (11)	0.0689 (11)	−0.0150 (8)	0.0135 (8)	−0.0252 (10)
N5	0.0387 (8)	0.0436 (8)	0.0419 (8)	−0.0041 (6)	0.0068 (6)	−0.0049 (6)
C6	0.0365 (9)	0.0442 (9)	0.0358 (9)	0.0014 (7)	0.0034 (7)	0.0019 (7)
C61	0.0441 (10)	0.0601 (11)	0.0534 (11)	0.0022 (9)	0.0113 (8)	−0.0105 (9)
O1S	0.0728 (10)	0.0551 (8)	0.0426 (8)	0.0036 (7)	−0.0031 (7)	0.0031 (6)
C1S	0.0870 (18)	0.0544 (13)	0.0731 (15)	−0.0019 (11)	0.0203 (13)	−0.0045 (11)

N1—C6	1.331 (2)	N5—C6	1.335 (2)
N1—C2	1.365 (2)	C6—C61	1.492 (2)
C2—N2	1.330 (2)	C61—H61A	0.9600
C2—N3	1.337 (2)	C61—H61B	0.9600
N2—H2B	0.87 (3)	C61—H61C	0.9600
N2—H2A	0.86 (2)	O1S—C1S	1.400 (2)
N3—C4	1.347 (2)	O1S—H1S	0.96 (4)
C4—N4	1.328 (2)	C1S—H1S1	0.9600
C4—N5	1.358 (2)	C1S—H1S2	0.9600
N4—H4B	0.89 (2)	C1S—H1S3	0.9600
N4—H4A	0.88 (2)
C6—N1—C2	114.47 (14)	N1—C6—C61	117.42 (15)
N2—C2—N3	118.93 (16)	N5—C6—C61	116.44 (16)
N2—C2—N1	116.28 (15)	C6—C61—H61A	109.5
N3—C2—N1	124.78 (16)	C6—C61—H61B	109.5
C2—N2—H2B	118.5 (17)	H61A—C61—H61B	109.5
C2—N2—H2A	118.6 (14)	C6—C61—H61C	109.5
H2B—N2—H2A	123 (2)	H61A—C61—H61C	109.5
C2—N3—C4	115.34 (14)	H61B—C61—H61C	109.5
N4—C4—N3	117.85 (16)	C1S—O1S—H1S	110 (2)
N4—C4—N5	117.65 (17)	O1S—C1S—H1S1	109.5
N3—C4—N5	124.49 (15)	O1S—C1S—H1S2	109.5
C4—N4—H4B	118.5 (15)	H1S1—C1S—H1S2	109.5
C4—N4—H4A	123.7 (14)	O1S—C1S—H1S3	109.5
H4B—N4—H4A	118 (2)	H1S1—C1S—H1S3	109.5
C6—N5—C4	114.73 (15)	H1S2—C1S—H1S3	109.5
N1—C6—N5	126.14 (15)
C6—N1—C2—N2	179.66 (15)	N4—C4—N5—C6	−178.87 (16)
C6—N1—C2—N3	0.7 (2)	N3—C4—N5—C6	2.1 (3)
N2—C2—N3—C4	179.99 (16)	C2—N1—C6—N5	1.3 (2)
N1—C2—N3—C4	−1.1 (3)	C2—N1—C6—C61	−178.50 (15)
C2—N3—C4—N4	−179.45 (16)	C4—N5—C6—N1	−2.6 (3)
C2—N3—C4—N5	−0.4 (3)	C4—N5—C6—C61	177.21 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1S···N5	0.96 (4)	1.86 (4)	2.816 (2)	176 (3)
N2—H2B···O1Si	0.87 (3)	2.26 (3)	3.093 (2)	160 (2)
N2—H2A···N1ii	0.86 (2)	2.20 (2)	3.060 (2)	180 (2)
N4—H4B···O1Siii	0.89 (2)	2.27 (2)	2.956 (2)	133.2 (19)
N4—H4A···N3iv	0.88 (2)	2.15 (2)	3.024 (2)	177.3 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1S—H1S⋯N5	0.96 (4)	1.86 (4)	2.816 (2)	176 (3)
N2—H2B⋯O1Si	0.87 (3)	2.26 (3)	3.093 (2)	160 (2)
N2—H2A⋯N1ii	0.86 (2)	2.20 (2)	3.060 (2)	180 (2)
N4—H4B⋯O1Siii	0.89 (2)	2.27 (2)	2.956 (2)	133.2 (19)
N4—H4A⋯N3iv	0.88 (2)	2.15 (2)	3.024 (2)	177.3 (19)

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