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

The crystal structure of the title compound, C(4)H(7)N(5)·C(2)H(6)O, is determined by extensive hydrogen bonding. A sequence of dimeric associations, formed by N-H(amino)⋯N(ring), connects the triazine rings into a mol-ecular tape. Mol-ecules are linked into a supra-molecular structure by N-H⋯O and O-H⋯O hydrogen bonds. The asymmetric unit consists of two formula units.

Related literature

For general background, see: Sebenik et al. (1989 ▶); Tashiro & Oiwa (1981 ▶).

Experimental

Crystal data

C4H7N5·C2H6O

M = 171.21

Triclinic,

a = 8.3860 (6) Å

b = 9.1514 (6) Å

c = 11.9104 (9) Å

α = 88.703 (1)°

β = 87.614 (2)°

γ = 76.668 (2)°

V = 888.56 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 (2) K

0.34 × 0.26 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.985

7627 measured reflections

3111 independent reflections

2619 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.07

3111 reflections

223 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000159/bq2061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000159/bq2061Isup2.hkl

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

C4H7N5·C2H6O	Z = 4
Mr = 171.21	F000 = 368.0
Triclinic, P1	Dx = 1.280 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.3860 (6) Å	Cell parameters from 3111 reflections
b = 9.1514 (6) Å	θ = 1.7–25.0º
c = 11.9104 (9) Å	µ = 0.09 mm−1
α = 88.703 (1)º	T = 273 (2) K
β = 87.614 (2)º	Block, colorless
γ = 76.668 (2)º	0.34 × 0.26 × 0.21 mm
V = 888.56 (11) Å3

Bruker CCD area-detector diffractometer	3111 independent reflections
Radiation source: fine-focus sealed tube	2619 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 273(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.975, Tmax = 0.985	k = −10→10
7627 measured reflections	l = −12→14

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0597P)2 + 0.2811P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3111 reflections	Δρmax = 0.25 e Å−3
223 parameters	Δρmin = −0.19 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
C1	0.0454 (2)	0.41963 (19)	0.15635 (15)	0.0388 (4)
H1A	−0.0653	0.4778	0.1527	0.058*
H1B	0.0892	0.3946	0.0817	0.058*
H1C	0.1110	0.4770	0.1920	0.058*
C2	0.04756 (19)	0.27874 (17)	0.22268 (13)	0.0290 (4)
C3	−0.07229 (18)	0.14537 (17)	0.34835 (13)	0.0258 (3)
C4	0.18337 (18)	0.04532 (17)	0.27722 (13)	0.0268 (3)
C5	0.6644 (3)	0.2978 (3)	0.0124 (2)	0.0651 (6)
H5A	0.7394	0.2012	0.0089	0.098*
H5B	0.7212	0.3716	0.0348	0.098*
H5C	0.6200	0.3244	−0.0602	0.098*
C6	0.5286 (2)	0.2917 (2)	0.09584 (17)	0.0486 (5)
H6A	0.5730	0.2628	0.1691	0.058*
H6B	0.4548	0.3900	0.1019	0.058*
C7	0.3737 (2)	0.18852 (18)	0.49621 (15)	0.0342 (4)
H7A	0.4172	0.1132	0.4412	0.051*
H7B	0.2683	0.1765	0.5241	0.051*
H7C	0.4469	0.1780	0.5572	0.051*
C8	0.35597 (18)	0.34072 (16)	0.44340 (12)	0.0254 (3)
C9	0.47170 (18)	0.50943 (16)	0.34763 (12)	0.0244 (3)
C10	0.20147 (18)	0.56977 (16)	0.39979 (12)	0.0255 (3)
N1	0.05944 (15)	0.02890 (14)	0.34824 (11)	0.0279 (3)
N2	0.18531 (16)	0.17023 (15)	0.21443 (11)	0.0299 (3)
N3	−0.08554 (15)	0.27267 (14)	0.28518 (11)	0.0284 (3)
N4	−0.20112 (16)	0.13534 (15)	0.41484 (11)	0.0323 (3)
H4A	−0.1984	0.0563	0.4559	0.039*
H4B	−0.2871	0.2079	0.4167	0.039*
N6	0.20797 (15)	0.43256 (14)	0.44771 (11)	0.0273 (3)
N7	0.49186 (15)	0.37128 (13)	0.39648 (10)	0.0268 (3)
N8	0.32886 (15)	0.61343 (14)	0.34805 (11)	0.0274 (3)
N9	0.05530 (15)	0.66659 (15)	0.40412 (12)	0.0336 (3)
H9A	0.0442	0.7546	0.3742	0.040*
H9B	−0.0276	0.6409	0.4368	0.040*
N10	0.60412 (15)	0.54140 (15)	0.29698 (11)	0.0309 (3)
H10A	0.5979	0.6276	0.2650	0.037*
H10B	0.6959	0.4759	0.2962	0.037*
O1	0.44204 (16)	0.18580 (16)	0.06094 (10)	0.0475 (4)
H1	0.3607	0.1897	0.1024	0.071*
C11	0.0989 (3)	0.1326 (3)	0.89654 (19)	0.0599 (6)
H11A	0.1324	0.1124	0.9725	0.090*
H11B	0.0321	0.0655	0.8769	0.090*
H11C	0.0370	0.2344	0.8900	0.090*
C12	0.2460 (2)	0.1100 (2)	0.81971 (17)	0.0495 (5)
H12A	0.3036	0.0053	0.8237	0.059*
H12B	0.2103	0.1310	0.7434	0.059*
N5	0.31467 (16)	−0.06868 (15)	0.26948 (12)	0.0353 (3)
H5D	0.3180	−0.1490	0.3091	0.042*
H5E	0.3961	−0.0619	0.2249	0.042*
O2	0.35702 (16)	0.19983 (16)	0.84251 (11)	0.0461 (3)
H2	0.3769	0.1931	0.9095	0.069*

	U11	U22	U33	U12	U13	U23
C1	0.0392 (10)	0.0326 (9)	0.0423 (10)	−0.0051 (7)	0.0017 (8)	0.0095 (8)
C2	0.0299 (8)	0.0272 (8)	0.0294 (8)	−0.0059 (7)	−0.0023 (6)	0.0018 (6)
C3	0.0241 (8)	0.0242 (8)	0.0282 (8)	−0.0041 (6)	−0.0011 (6)	−0.0001 (6)
C4	0.0250 (8)	0.0267 (8)	0.0281 (8)	−0.0051 (6)	−0.0004 (6)	0.0010 (6)
C5	0.0531 (13)	0.0762 (16)	0.0747 (16)	−0.0344 (12)	0.0045 (11)	0.0046 (12)
C6	0.0485 (11)	0.0488 (11)	0.0516 (12)	−0.0174 (9)	0.0003 (9)	−0.0063 (9)
C7	0.0298 (9)	0.0250 (8)	0.0454 (10)	−0.0028 (7)	0.0032 (7)	0.0040 (7)
C8	0.0248 (8)	0.0233 (8)	0.0269 (8)	−0.0032 (6)	0.0004 (6)	−0.0019 (6)
C9	0.0251 (8)	0.0230 (7)	0.0242 (8)	−0.0037 (6)	0.0001 (6)	−0.0011 (6)
C10	0.0237 (8)	0.0244 (8)	0.0270 (8)	−0.0028 (6)	−0.0012 (6)	−0.0002 (6)
N1	0.0247 (7)	0.0251 (7)	0.0313 (7)	−0.0019 (5)	0.0038 (5)	0.0036 (5)
N2	0.0293 (7)	0.0285 (7)	0.0311 (7)	−0.0062 (6)	0.0035 (5)	0.0031 (6)
N3	0.0257 (7)	0.0258 (7)	0.0321 (7)	−0.0030 (5)	0.0003 (5)	0.0039 (5)
N4	0.0258 (7)	0.0250 (7)	0.0419 (8)	0.0007 (5)	0.0089 (6)	0.0058 (6)
N6	0.0237 (7)	0.0234 (7)	0.0334 (7)	−0.0032 (5)	0.0008 (5)	0.0007 (5)
N7	0.0241 (7)	0.0228 (7)	0.0312 (7)	−0.0013 (5)	0.0016 (5)	0.0015 (5)
N8	0.0251 (7)	0.0239 (7)	0.0309 (7)	−0.0016 (5)	0.0009 (5)	0.0026 (5)
N9	0.0223 (7)	0.0269 (7)	0.0478 (9)	0.0005 (5)	0.0038 (6)	0.0078 (6)
N10	0.0237 (7)	0.0253 (7)	0.0411 (8)	−0.0017 (5)	0.0039 (6)	0.0054 (6)
O1	0.0477 (8)	0.0614 (9)	0.0398 (7)	−0.0274 (7)	0.0112 (6)	−0.0083 (6)
C11	0.0513 (12)	0.0746 (15)	0.0606 (14)	−0.0303 (11)	0.0095 (10)	−0.0034 (11)
C12	0.0453 (11)	0.0601 (13)	0.0463 (11)	−0.0190 (10)	0.0023 (9)	−0.0044 (9)
N5	0.0260 (7)	0.0298 (7)	0.0455 (8)	0.0005 (6)	0.0105 (6)	0.0072 (6)
O2	0.0461 (8)	0.0581 (8)	0.0391 (7)	−0.0241 (6)	0.0010 (6)	0.0112 (6)

C1—C2	1.494 (2)	C8—N7	1.3327 (19)
C1—H1A	0.9600	C9—N10	1.3300 (19)
C1—H1B	0.9600	C9—N8	1.3471 (19)
C1—H1C	0.9600	C9—N7	1.3571 (19)
C2—N3	1.327 (2)	C10—N9	1.3364 (19)
C2—N2	1.340 (2)	C10—N8	1.3459 (19)
C3—N4	1.332 (2)	C10—N6	1.3580 (19)
C3—N1	1.3466 (19)	N4—H4A	0.8600
C3—N3	1.3576 (19)	N4—H4B	0.8600
C4—N5	1.332 (2)	N9—H9A	0.8600
C4—N1	1.346 (2)	N9—H9B	0.8600
C4—N2	1.355 (2)	N10—H10A	0.8600
C5—C6	1.490 (3)	N10—H10B	0.8600
C5—H5A	0.9600	O1—H1	0.8200
C5—H5B	0.9600	C11—C12	1.482 (3)
C5—H5C	0.9600	C11—H11A	0.9600
C6—O1	1.417 (2)	C11—H11B	0.9600
C6—H6A	0.9700	C11—H11C	0.9600
C6—H6B	0.9700	C12—O2	1.415 (2)
C7—C8	1.494 (2)	C12—H12A	0.9700
C7—H7A	0.9600	C12—H12B	0.9700
C7—H7B	0.9600	N5—H5D	0.8600
C7—H7C	0.9600	N5—H5E	0.8600
C8—N6	1.3285 (19)	O2—H2	0.8200
C2—C1—H1A	109.5	N10—C9—N7	116.38 (13)
C2—C1—H1B	109.5	N8—C9—N7	124.41 (13)
H1A—C1—H1B	109.5	N9—C10—N8	118.57 (13)
C2—C1—H1C	109.5	N9—C10—N6	116.26 (13)
H1A—C1—H1C	109.5	N8—C10—N6	125.17 (13)
H1B—C1—H1C	109.5	C4—N1—C3	114.56 (13)
N3—C2—N2	125.90 (14)	C2—N2—C4	114.89 (13)
N3—C2—C1	117.42 (14)	C2—N3—C3	114.50 (13)
N2—C2—C1	116.68 (14)	C3—N4—H4A	120.0
N4—C3—N1	117.82 (13)	C3—N4—H4B	120.0
N4—C3—N3	116.89 (13)	H4A—N4—H4B	120.0
N1—C3—N3	125.28 (13)	C8—N6—C10	114.35 (12)
N5—C4—N1	117.59 (14)	C8—N7—C9	114.99 (12)
N5—C4—N2	117.68 (13)	C10—N8—C9	114.81 (12)
N1—C4—N2	124.72 (14)	C10—N9—H9A	120.0
C6—C5—H5A	109.5	C10—N9—H9B	120.0
C6—C5—H5B	109.5	H9A—N9—H9B	120.0
H5A—C5—H5B	109.5	C9—N10—H10A	120.0
C6—C5—H5C	109.5	C9—N10—H10B	120.0
H5A—C5—H5C	109.5	H10A—N10—H10B	120.0
H5B—C5—H5C	109.5	C6—O1—H1	109.5
O1—C6—C5	109.36 (17)	C12—C11—H11A	109.5
O1—C6—H6A	109.8	C12—C11—H11B	109.5
C5—C6—H6A	109.8	H11A—C11—H11B	109.5
O1—C6—H6B	109.8	C12—C11—H11C	109.5
C5—C6—H6B	109.8	H11A—C11—H11C	109.5
H6A—C6—H6B	108.3	H11B—C11—H11C	109.5
C8—C7—H7A	109.5	O2—C12—C11	114.80 (17)
C8—C7—H7B	109.5	O2—C12—H12A	108.6
H7A—C7—H7B	109.5	C11—C12—H12A	108.6
C8—C7—H7C	109.5	O2—C12—H12B	108.6
H7A—C7—H7C	109.5	C11—C12—H12B	108.6
H7B—C7—H7C	109.5	H12A—C12—H12B	107.5
N6—C8—N7	126.22 (13)	C4—N5—H5D	120.0
N6—C8—C7	117.53 (13)	C4—N5—H5E	120.0
N7—C8—C7	116.25 (13)	H5D—N5—H5E	120.0
N10—C9—N8	119.21 (13)	C12—O2—H2	109.5
N5—C4—N1—C3	−177.19 (14)	N7—C8—N6—C10	−0.8 (2)
N2—C4—N1—C3	3.9 (2)	C7—C8—N6—C10	178.93 (13)
N4—C3—N1—C4	178.53 (14)	N9—C10—N6—C8	−178.84 (13)
N3—C3—N1—C4	−0.9 (2)	N8—C10—N6—C8	2.1 (2)
N3—C2—N2—C4	−0.2 (2)	N6—C8—N7—C9	−1.2 (2)
C1—C2—N2—C4	178.97 (14)	C7—C8—N7—C9	179.03 (13)
N5—C4—N2—C2	177.66 (14)	N10—C9—N7—C8	−177.94 (13)
N1—C4—N2—C2	−3.4 (2)	N8—C9—N7—C8	2.4 (2)
N2—C2—N3—C3	2.9 (2)	N9—C10—N8—C9	179.85 (13)
C1—C2—N3—C3	−176.34 (14)	N6—C10—N8—C9	−1.1 (2)
N4—C3—N3—C2	178.33 (14)	N10—C9—N8—C10	179.00 (13)
N1—C3—N3—C2	−2.3 (2)	N7—C9—N8—C10	−1.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···N7i	0.86	2.11	2.9666 (18)	171
N5—H5D···N8ii	0.86	2.19	3.0132 (19)	159
N5—H5E···O2iii	0.86	2.29	3.0071 (19)	142
N10—H10A···O2iv	0.86	2.10	2.9337 (18)	163
O2—H2···O1v	0.82	1.90	2.7185 (18)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯N7i	0.86	2.11	2.9666 (18)	171
N5—H5D⋯N8ii	0.86	2.19	3.0132 (19)	159
N5—H5E⋯O2iii	0.86	2.29	3.0071 (19)	142
N10—H10A⋯O2iv	0.86	2.10	2.9337 (18)	163
O2—H2⋯O1v	0.82	1.90	2.7185 (18)	174

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