4-Amino-2,3,5-trimethyl-pyridine monohydrate.

In the title compound, C(8)H(12)N(2)·H(2)O, four substituted pyridine mol-ecules alternate with four water mol-ecules, forming a large ring via O(water)-H⋯N(pyridine) and N(amine)-H⋯O(water) hydrogen bonding. Adjacent rings are connected via O(water)-H⋯O(water) hydrogen-bonds, forming a three-dimensional network.

Related literature

For pyridine-amine derivatives, see: Smith et al. (2005 ▶); Tsuzuki et al. (2005 ▶). For their role as chemical inter­mediates in the formation of diverse mol­ecules possessing biological activity, see: Birault et al. (2005 ▶); Gordon et al. (1996 ▶); Player et al. (2007 ▶). For related structures, see: Li et al. (2008 ▶); Lin et al. (2005 ▶); Xie et al. (2008 ▶); Yu et al. (2005 ▶); Zhou et al. (2005 ▶). For the extinction correction, see: Larson (1970 ▶).

Experimental

Crystal data

C8H12N2·H2O

M = 154.21

Tetragonal,

a = 19.5710 (9) Å

c = 4.8819 (2) Å

V = 1869.89 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.33 × 0.27 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.967, T max = 0.984

17243 measured reflections

1250 independent reflections

951 reflections with F 2 > 2.0σ(F 2)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.00

1250 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2007 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ▶); 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 General, I. DOI: 10.1107/S1600536809016833/fl2246sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016833/fl2246Isup2.hkl

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

C8H12N2·H2O	Dx = 1.095 Mg m−3
Mr = 154.21	Mo Kα radiation, λ = 0.71075 Å
Tetragonal, P421c	Cell parameters from 10766 reflections
Hall symbol: P -4 2n	θ = 3.3–27.4°
a = 19.5710 (9) Å	µ = 0.07 mm−1
c = 4.8819 (2) Å	T = 296 K
V = 1869.89 (14) Å3	Chunk, colorless
Z = 8	0.33 × 0.27 × 0.22 mm
F(000) = 672.00

Rigaku R-AXIS RAPID diffractometer	951 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.045
ω scans	θmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −25→25
Tmin = 0.967, Tmax = 0.984	k = −25→25
17243 measured reflections	l = −6→5
1250 independent reflections

Refinement on F2	w = 1/[0.0001Fo2 + 1.1100σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.035	(Δ/σ)max < 0.001
wR(F2) = 0.088	Δρmax = 0.23 e Å−3
S = 1.00	Δρmin = −0.20 e Å−3
1250 reflections	Extinction correction: Larson (1970)
101 parameters	Extinction coefficient: 460 (64)
H-atom parameters constrained

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
O1	0.25888 (6)	0.28901 (6)	0.2514 (3)	0.0571 (4)
N1	0.23938 (11)	0.42486 (10)	0.3906 (4)	0.0581 (6)
N2	0.19626 (9)	0.61921 (9)	0.6961 (4)	0.0534 (6)
C1	0.27642 (12)	0.47949 (12)	0.3109 (5)	0.0528 (7)
C2	0.26474 (11)	0.54519 (11)	0.4090 (5)	0.0472 (6)
C3	0.21206 (11)	0.55487 (11)	0.6011 (4)	0.0427 (6)
C4	0.17323 (12)	0.49824 (12)	0.6859 (4)	0.0465 (6)
C5	0.18992 (12)	0.43602 (12)	0.5762 (5)	0.0556 (8)
C6	0.33136 (13)	0.46412 (12)	0.1049 (7)	0.0756 (9)
C7	0.30672 (12)	0.60551 (12)	0.3136 (6)	0.0690 (9)
C8	0.11654 (12)	0.50507 (12)	0.8924 (5)	0.0603 (7)
H5	0.1649	0.3984	0.6350	0.067*
H61	0.3753	0.4674	0.1913	0.091*
H62	0.3251	0.4187	0.0345	0.091*
H63	0.3288	0.4964	−0.0428	0.091*
H71	0.3290	0.5943	0.1442	0.083*
H72	0.2774	0.6442	0.2865	0.083*
H73	0.3405	0.6163	0.4495	0.083*
H81	0.1353	0.5184	1.0660	0.072*
H82	0.0847	0.5391	0.8315	0.072*
H83	0.0935	0.4620	0.9113	0.072*
H101	0.2530	0.3317	0.2901	0.069*
H102	0.2457	0.2771	0.0921	0.069*
H201	0.1755	0.6229	0.8489	0.064*
H202	0.2266	0.6511	0.6743	0.064*

	U11	U22	U33	U12	U13	U23
O1	0.0663 (10)	0.0465 (9)	0.0584 (10)	0.0063 (8)	−0.0044 (9)	−0.0047 (9)
N1	0.0701 (14)	0.0454 (11)	0.0587 (14)	0.0003 (10)	0.0039 (14)	−0.0022 (11)
N2	0.0624 (13)	0.0433 (11)	0.0545 (12)	−0.0029 (9)	0.0092 (11)	−0.0006 (10)
C1	0.0563 (16)	0.0549 (16)	0.0471 (14)	0.0083 (12)	0.0024 (13)	−0.0024 (13)
C2	0.0504 (14)	0.0454 (14)	0.0459 (13)	0.0003 (11)	0.0032 (14)	0.0021 (13)
C3	0.0472 (13)	0.0398 (12)	0.0411 (12)	0.0003 (10)	−0.0022 (12)	0.0001 (12)
C4	0.0507 (14)	0.0452 (13)	0.0435 (12)	−0.0002 (12)	−0.0022 (12)	0.0036 (13)
C5	0.0658 (17)	0.0454 (15)	0.0557 (15)	−0.0047 (12)	0.0015 (15)	0.0042 (14)
C6	0.086 (2)	0.0690 (19)	0.0717 (19)	0.0162 (16)	0.021 (2)	−0.0020 (18)
C7	0.0674 (17)	0.0627 (17)	0.077 (2)	−0.0054 (14)	0.0164 (17)	0.0013 (16)
C8	0.0640 (16)	0.0609 (15)	0.0562 (14)	−0.0072 (13)	0.0067 (15)	0.0060 (16)

N1—C1	1.349 (3)	N2—H201	0.852
N1—C5	1.344 (3)	N2—H202	0.868
N2—C3	1.377 (2)	C5—H5	0.930
C1—C2	1.391 (3)	C6—H61	0.960
C1—C6	1.503 (3)	C6—H62	0.960
C2—C3	1.407 (3)	C6—H63	0.960
C2—C7	1.512 (3)	C7—H71	0.960
C3—C4	1.406 (3)	C7—H72	0.960
C4—C5	1.370 (3)	C7—H73	0.960
C4—C8	1.505 (3)	C8—H81	0.960
O1—H101	0.864	C8—H82	0.960
O1—H102	0.852	C8—H83	0.960
C1—N1—C5	116.9 (2)	C4—C5—H5	117.3
N1—C1—C2	123.0 (2)	C1—C6—H61	109.5
N1—C1—C6	114.8 (2)	C1—C6—H62	109.5
C2—C1—C6	122.2 (2)	C1—C6—H63	109.5
C1—C2—C3	118.3 (2)	H61—C6—H62	109.5
C1—C2—C7	121.8 (2)	H61—C6—H63	109.5
C3—C2—C7	119.9 (2)	H62—C6—H63	109.5
N2—C3—C2	120.82 (19)	C2—C7—H71	109.5
N2—C3—C4	120.0 (2)	C2—C7—H72	109.5
C2—C3—C4	119.1 (2)	C2—C7—H73	109.5
C3—C4—C5	117.2 (2)	H71—C7—H72	109.5
C3—C4—C8	121.7 (2)	H71—C7—H73	109.5
C5—C4—C8	121.1 (2)	H72—C7—H73	109.5
N1—C5—C4	125.4 (2)	C4—C8—H81	109.5
H101—O1—H102	115.0	C4—C8—H82	109.5
C3—N2—H201	118.6	C4—C8—H83	109.5
C3—N2—H202	117.5	H81—C8—H82	109.5
H201—N2—H202	111.9	H81—C8—H83	109.5
N1—C5—H5	117.3	H82—C8—H83	109.5
C1—N1—C5—C4	1.5 (3)	C7—C2—C3—N2	2.6 (3)
C5—N1—C1—C2	−0.9 (3)	C7—C2—C3—C4	179.6 (2)
C5—N1—C1—C6	179.6 (2)	N2—C3—C4—C5	177.6 (2)
N1—C1—C2—C3	0.3 (3)	N2—C3—C4—C8	−3.5 (3)
N1—C1—C2—C7	−179.4 (2)	C2—C3—C4—C5	0.6 (3)
C6—C1—C2—C3	179.8 (2)	C2—C3—C4—C8	179.5 (2)
C6—C1—C2—C7	0.1 (2)	C3—C4—C5—N1	−1.3 (3)
C1—C2—C3—N2	−177.1 (2)	C8—C4—C5—N1	179.8 (2)
C1—C2—C3—C4	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···N1	0.86	1.91	2.771 (2)	178
O1—H102···O1i	0.85	1.93	2.778 (2)	173
N2—H202···O1ii	0.87	2.17	3.009 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H101⋯N1	0.86	1.91	2.771 (2)	178
O1—H102⋯O1i	0.85	1.93	2.778 (2)	173
N2—H202⋯O1ii	0.87	2.17	3.009 (2)	161

Symmetry codes: (i) ; (ii) .