1-(2-Methyl-imidazo[1,2-a]pyridin-3-yl)-3,3-bis-(methyl-sulfan-yl)prop-2-enone monohydrate.

The title compound, C(13)H(14)N(2)OS(2)·H(2)O, appears in the form of bimolecular aggregate in which mol-ecular components are linked by O-H⋯N hydrogen bonding. The nine-membered imidazo[1,2-a]pyridine system is almost planar, with a mean deviation of 0.026 (1) Å. An intra-molecular C-H⋯O hydrogen bond forms within the imidazo[1,2-a]pyridine system. The crystal packing is consolidated by O-H⋯O and C-H⋯O hydrogen bonds, forming a supra-molecular structure consisting of perpendicular infinite mol-ecular chains running along the a and c axes.

Related literature

For related structures, see: Bibila Mayaya Bisseyou et al. (2007 ▶, 2009 ▶); Duan et al.(2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H14N2OS2·H2O

M = 296.41

Orthorhombic,

a = 5.1405 (1) Å

b = 17.7653 (3) Å

c = 31.3919 (6) Å

V = 2866.79 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.37 mm−1

T = 295 K

0.25 × 0.15 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶) T min = 0.90, T max = 0.95

11253 measured reflections

4202 independent reflections

2344 reflections with I > 2σ(I)

R int = 0.05

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.097

S = 0.99

4202 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 1997 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023514/bq2145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023514/bq2145Isup2.hkl

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

C13H14N2OS2·H2O	Dx = 1.373 Mg m−3
Mr = 296.41	Melting point: 430 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 11253 reflections
a = 5.1405 (1) Å	θ = 4–30°
b = 17.7653 (3) Å	µ = 0.37 mm−1
c = 31.3919 (6) Å	T = 295 K
V = 2866.79 (9) Å3	Prism, orange
Z = 8	0.25 × 0.15 × 0.15 mm
F(000) = 1248

Nonius KappaCCD diffractometer	2344 reflections with I > 3σ(I)
graphite	Rint = 0.05
φ scans	θmax = 30.5°, θmin = 1.3°
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997)	h = 0→7
Tmin = 0.90, Tmax = 0.95	k = 0→25
11253 measured reflections	l = 0→43
4202 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(F2) + (0.04P)2 + 3.2P], where P = [max(Fo2,0) + 2Fc2]/3
S = 0.99	(Δ/σ)max = 0.0002
2066 reflections	Δρmax = 0.18 e Å−3
172 parameters	Δρmin = −0.25 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
S1	0.01264 (14)	0.40723 (4)	0.05322 (3)	0.0552
S2	−0.11568 (16)	0.46016 (4)	0.14025 (3)	0.0696
O1	0.3999 (4)	0.30577 (10)	0.05889 (6)	0.0542
N1	0.7820 (4)	0.21236 (11)	0.09663 (7)	0.0394
O2w	0.9388 (4)	0.07731 (12)	0.22997 (7)	0.0739
N2	0.8459 (5)	0.18741 (13)	0.16574 (8)	0.0559
C4	0.8270 (5)	0.20481 (13)	0.05354 (9)	0.0464
C7	0.9265 (5)	0.17257 (14)	0.12603 (9)	0.0474
C9	0.2551 (5)	0.35366 (14)	0.12396 (9)	0.0472
C5	0.6013 (5)	0.25573 (13)	0.11962 (8)	0.0410
C3	1.0207 (6)	0.15826 (14)	0.04040 (10)	0.0525
C2	1.1724 (6)	0.11813 (15)	0.06988 (11)	0.0573
C1	1.1255 (6)	0.12480 (15)	0.11196 (11)	0.0561
C6	0.6478 (5)	0.23742 (16)	0.16209 (9)	0.0494
C10	0.0715 (5)	0.40096 (14)	0.10800 (9)	0.0473
C8	0.4160 (5)	0.30513 (13)	0.09821 (9)	0.0417
C11	−0.2533 (6)	0.47334 (16)	0.04946 (12)	0.0704
C13	0.5083 (7)	0.2619 (2)	0.20158 (10)	0.0723
C12	0.0018 (9)	0.4409 (2)	0.19285 (13)	0.0992
H2	1.3072	0.0877	0.0601	0.0687*
H4	0.7197	0.2326	0.0346	0.0557*
H9	0.2801	0.3530	0.1530	0.0562*
H1	1.2232	0.0990	0.1323	0.0665*
H113	−0.2078	0.5201	0.0623	0.1052*
H112	−0.2875	0.4811	0.0199	0.1058*
H111	−0.4050	0.4535	0.0630	0.1059*
H3	1.0530	0.1538	0.0113	0.0637*
H132	0.5316	0.3152	0.2061	0.1075*
H133	0.3256	0.2531	0.1989	0.1079*
H131	0.5739	0.2357	0.2257	0.1077*
H22w	1.0875	0.0824	0.2392	0.1108*
H123	−0.0206	0.3876	0.1991	0.1488*
H21w	0.9353	0.1136	0.2140	0.1109*
H122	0.1833	0.4544	0.1939	0.1486*
H121	−0.0960	0.4706	0.2124	0.1492*

	U11	U22	U33	U12	U13	U23
S1	0.0444 (4)	0.0482 (4)	0.0731 (5)	0.0067 (3)	−0.0097 (4)	0.0037 (4)
S2	0.0549 (5)	0.0552 (4)	0.0988 (7)	0.0090 (4)	0.0082 (4)	−0.0195 (4)
O1	0.0542 (11)	0.0608 (12)	0.0477 (13)	0.0151 (9)	−0.0031 (10)	0.0060 (9)
N1	0.0375 (11)	0.0360 (10)	0.0448 (12)	−0.0011 (9)	−0.0041 (10)	0.0044 (9)
O2w	0.0700 (15)	0.0794 (15)	0.0723 (16)	−0.0039 (12)	−0.0076 (12)	0.0241 (12)
N2	0.0551 (15)	0.0623 (15)	0.0501 (15)	0.0054 (12)	−0.0097 (12)	0.0093 (12)
C4	0.0497 (16)	0.0397 (13)	0.0496 (17)	0.0002 (11)	0.0008 (12)	0.0037 (12)
C7	0.0416 (15)	0.0434 (13)	0.0572 (18)	0.0000 (11)	−0.0097 (13)	0.0060 (13)
C9	0.0414 (14)	0.0488 (14)	0.0515 (16)	0.0037 (12)	0.0006 (13)	−0.0051 (12)
C5	0.0362 (13)	0.0405 (13)	0.0464 (16)	−0.0010 (11)	−0.0001 (12)	0.0028 (11)
C3	0.0550 (17)	0.0431 (14)	0.0594 (18)	0.0028 (13)	0.0065 (14)	−0.0017 (12)
C2	0.0493 (17)	0.0444 (15)	0.078 (2)	0.0084 (13)	0.0018 (15)	−0.0043 (15)
C1	0.0497 (17)	0.0448 (14)	0.074 (2)	0.0076 (13)	−0.0120 (15)	0.0049 (14)
C6	0.0454 (15)	0.0552 (16)	0.0476 (17)	0.0005 (13)	−0.0047 (13)	0.0023 (13)
C10	0.0356 (14)	0.0381 (13)	0.068 (2)	−0.0033 (11)	0.0012 (12)	−0.0048 (12)
C8	0.0356 (13)	0.0400 (12)	0.0495 (17)	−0.0016 (10)	−0.0039 (12)	0.0026 (12)
C11	0.0485 (17)	0.0517 (17)	0.111 (3)	0.0064 (14)	−0.0165 (19)	0.0092 (18)
C13	0.076 (2)	0.098 (2)	0.0430 (18)	0.015 (2)	−0.0014 (17)	0.0030 (17)
C12	0.112 (3)	0.105 (3)	0.081 (3)	0.021 (3)	0.016 (2)	−0.035 (2)

S1—C10	1.750 (3)	C5—C6	1.393 (4)
S1—C11	1.806 (3)	C5—C8	1.459 (3)
S2—C10	1.748 (3)	C3—C2	1.405 (4)
S2—C12	1.791 (4)	C3—H3	0.930
O1—C8	1.237 (3)	C2—C1	1.348 (4)
N1—C4	1.379 (3)	C2—H2	0.931
N1—C7	1.380 (3)	C1—H1	0.932
N1—C5	1.406 (3)	C6—C13	1.496 (4)
O2w—H22w	0.822	C11—H113	0.952
O2w—H21w	0.817	C11—H112	0.954
N2—C7	1.340 (4)	C11—H111	0.955
N2—C6	1.356 (3)	C13—H132	0.966
C4—C3	1.358 (4)	C13—H133	0.956
C4—H4	0.948	C13—H131	0.951
C7—C1	1.401 (4)	C12—H123	0.974
C9—C10	1.359 (3)	C12—H122	0.964
C9—C8	1.443 (4)	C12—H121	0.953
C9—H9	0.922
C10—S1—C11	103.68 (15)	C5—C6—N2	111.3 (2)
C10—S2—C12	103.50 (16)	C5—C6—C13	130.0 (3)
C4—N1—C7	121.1 (2)	N2—C6—C13	118.7 (3)
C4—N1—C5	131.9 (2)	S1—C10—S2	115.83 (15)
C7—N1—C5	107.0 (2)	S1—C10—C9	121.4 (2)
H22w—O2w—H21w	98.6	S2—C10—C9	122.7 (2)
C7—N2—C6	106.4 (2)	C5—C8—C9	118.4 (2)
N1—C4—C3	118.7 (3)	C5—C8—O1	120.6 (2)
N1—C4—H4	117.7	C9—C8—O1	121.0 (2)
C3—C4—H4	123.6	S1—C11—H113	110.7
N1—C7—N2	110.8 (2)	S1—C11—H112	107.3
N1—C7—C1	119.5 (3)	H113—C11—H112	109.3
N2—C7—C1	129.7 (3)	S1—C11—H111	110.4
C10—C9—C8	124.1 (3)	H113—C11—H111	109.6
C10—C9—H9	118.0	H112—C11—H111	109.5
C8—C9—H9	117.8	C6—C13—H132	110.3
N1—C5—C6	104.5 (2)	C6—C13—H133	110.5
N1—C5—C8	121.6 (2)	H132—C13—H133	107.1
C6—C5—C8	133.9 (2)	C6—C13—H131	110.4
C4—C3—C2	121.1 (3)	H132—C13—H131	108.6
C4—C3—H3	118.7	H133—C13—H131	109.9
C2—C3—H3	120.3	S2—C12—H123	109.3
C3—C2—C1	120.1 (3)	S2—C12—H122	108.2
C3—C2—H2	119.3	H123—C12—H122	110.5
C1—C2—H2	120.5	S2—C12—H121	108.0
C7—C1—C2	119.5 (3)	H123—C12—H121	110.3
C7—C1—H1	118.4	H122—C12—H121	110.5
C2—C1—H1	122.0

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.95	2.23	2.840 (4)	121
C3—H3···O1i	0.93	2.45	3.242 (4)	143
O2w—H22w···O2wii	0.82	2.05	2.862 (4)	168
O2w—H21w···N2	0.82	2.06	2.849 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1	0.95	2.23	2.840 (4)	121
C3—H3⋯O1i	0.93	2.45	3.242 (4)	143
O2w—H22w⋯O2wii	0.82	2.05	2.862 (4)	168
O2w—H21w⋯N2	0.82	2.06	2.849 (4)	164

Symmetry codes: (i) ; (ii) .