1-(2-Methyl­imidazo[1,2-a]pyridin-3-yl)-3,3-bis­(methyl­sulfan­yl)prop-2-enone monohydrate

Bibila Mayaya Bisseyou, Y.; Sissouma, D.; Goulizan Bi, S.D.; Ouattara, M.; Yao-Kakou, R.C.A.

doi:10.1107/S1600536809023514

organic compounds

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Volume 65| Part 7| July 2009| Pages o1698-o1699

doi:10.1107/S1600536809023514

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1-(2-Methylimidazo[1,2-a]pyridin-3-yl)-3,3-bis(methylsulfanyl)prop-2-enone monohydrate

Yvon Bibila Mayaya Bisseyou,^a ^* Drissa Sissouma,^b Severin D. Goulizan Bi,^a Mahama Ouattara ^c and R. C. A. Yao-Kakou ^a

^aLaboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d'Ivoire, ^bLaboratoire de Chimie Organique Structurale, UFR SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d'Ivoire, and ^cLaboratoire de Chimie Thérapeutique et Synthèse de Médicaments, UFR Sciences Pharmaceutiques, Université de Cocody, 01 BP V 34 Abidjan 01, Côte d'Ivoire
^*Correspondence e-mail: bibilamayayabisseyou@yahoo.fr

(Received 15 May 2009; accepted 18 June 2009; online 27 June 2009)

The title compound, C₁₃H₁₄N₂OS₂·H₂O, appears in the form of bimolecular aggregate in which molecular 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 intramolecular 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 supramolecular structure consisting of perpendicular infinite molecular 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_r = 296.41
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.097
S = 0.99
4202 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

As part of continuing work on heterocyclic compounds biologically active, we have synthesized new derivative in order to explore new potential activities or to improve known properties of this compound class. Asymmetric unit of title compound which crystallize as the monohydrate is consist of two independent molecular components connected between them by an O—H···N hydrogen bond forming thus one bimolecular aggregate (Fig. 1). In the imidazo[1,2-a]pyridine component, the values of bond lengths and angles of nine-membered imidazopyridine ring are similar to those found in previous studies (Bibila Mayaya Bisseyou et al., 2007, 2009, Duan et al., 2006). Imidazopyridine ring, essentially planar with mean deviation of 0.026 (1)Å, makes dihedral angles of 6.11 (23)° and 9.79 (15)° with P1(C9/C10/S1/C11) and P2(C9/C10/S2/C12) mean planes, respectively. Besides, we also note within of the same component, the presence of C—H···O intra-molecular hydrogen bond (Table 1) generating an S(6) motif (Bernstein et al., 1995). The three-dimensional crystal packing is consolidated by inter-bimolecular aggregate hydrogen bonds (Fig. 2). Indeed, each bimolecular unit is linked to three others via O—H···O and C—H···O hydrogen bonds (Table 1) forming thus a supra-molecular structure consisted of to two perpendicular infinite chain types: the first one is established by bimolecular aggregates along c axis; the second one is parallel to a axis and constituted only by water molecules in zigzag fashion.

Related literature top

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

Experimental top

1-(2-methylimidazo[1,2-a]pyridine-3-yl) acetyl (1 g, 6.2 mmol) was dissolved in distilled dimethyl sulfoxide (15 ml), and the carbon disulfur (0.41 ml, 6.8 mmol) was added. After cooling of the mixture at 0°C, sodium hydrure (0.36 g, 15.4 mmol) was added. After stirring for 30 minutes at 0°C, the mixture was stirred at ambient temperature during 4 h. Solution was then cooled at 0°C and methyl iodide (2.5 molar equivalents) was added dropwise. The resulting mixture was then left under stirring during 24 h then poured into 50 ml ice-cold water. The precipitate was filtered and recrystallized from mixture of water-dioxane (2:1) to obtain orange single crystals of title compound (1.31 g; yield, 80%, m.p.: 430 K)

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); 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 (Betteridge et al., 2003).

Figures top

	Fig. 1. The molecular structure of the title compound and the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius. Dashed lines indicate hydrogen bonds.
	Fig. 2. Crystal packing of the title compound, viewed down the a axis, showing the both perpendicular infinite chain types. The first one is established by bimolecular aggregates along c axis; the second one is parallel to a axis and constituted only by water molecules in zigzag fashion. H atoms not involved in hydrogen bonds have been omitted for clarity. Dashed lines indicate hydrogen bonds.

1-(2-Methylimidazo[1,2-a]pyridin-3-yl)-3,3-bis(methylsulfanyl)prop- 2-enone monohydrate top

Crystal data top

C₁₃H₁₄N₂OS₂·H₂O	D_x = 1.373 Mg m⁻³
M_r = 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

Data collection top

Nonius KappaCCD diffractometer	2344 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.05
ϕ scans	θ_max = 30.5°, θ_min = 1.3°
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997)	h = 0→7
T_min = 0.90, T_max = 0.95	k = 0→25
11253 measured reflections	l = 0→43
4202 independent reflections

Refinement top

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(F_o²,0) + 2F_c²]/3
S = 0.99	(Δ/σ)_max = 0.000155
2066 reflections	Δρ_max = 0.18 e Å⁻³
172 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Crystal data top

C₁₃H₁₄N₂OS₂·H₂O	V = 2866.79 (9) Å³
M_r = 296.41	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 5.1405 (1) Å	µ = 0.37 mm⁻¹
b = 17.7653 (3) Å	T = 295 K
c = 31.3919 (6) Å	0.25 × 0.15 × 0.15 mm

Data collection top

Nonius KappaCCD diffractometer	4202 independent reflections
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997)	2344 reflections with I > 3σ(I)
T_min = 0.90, T_max = 0.95	R_int = 0.05
11253 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 0.99	Δρ_max = 0.18 e Å⁻³
2066 reflections	Δρ_min = −0.25 e Å⁻³
172 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, −z; (ii) x+1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₂OS₂·H₂O
M_r	296.41
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	5.1405 (1), 17.7653 (3), 31.3919 (6)
V (Å³)	2866.79 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.25 × 0.15 × 0.15

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997)
T_min, T_max	0.90, 0.95
No. of measured, independent and observed [I > 3σ(I)] reflections	11253, 4202, 2344
R_int	0.05
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.097, 0.99
No. of reflections	2066
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.25

Computer programs: COLLECT (Nonius, 1997), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, −z; (ii) x+1/2, y, −z+1/2.

Acknowledgements

The authors thank the Spectropôle Service of the Faculty of Sciences and Techniques of Saint Jérôme (France) for the use of their diffractometer.

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-(2-Methyl­imidazo[1,2-a]pyridin-3-yl)-3,3-bis­­(methyl­sulfan­yl)prop-2-enone monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-(2-Methylimidazo[1,2-a]pyridin-3-yl)-3,3-bis(methylsulfanyl)prop-2-enone monohydrate