Ethyl 6-methyl-sulfanyl-2-phenyl-1H-imidazo[1,2-b]pyrazole-7-carboxyl-ate monohydrate.

The title compound, C(15)H(15)N(3)O(2)S·H(2)O, has been obtained in a search for new imidazo[1,2-b]pyrazole derivatives with better biological activity. The 1H-imidazo[1,2-b]pyrazole plane forms a dihedral angle of 16.90 (3)° with the benzene ring. π-π inter-actions are indicated by the short distance of 3.643 (2) Å between the centroids of the benzene and imidazole rings. The crystal structure also involves inter-molecular O-H⋯N hydrogen bonds.

Related literature

For the biological activity of imidazo[1,2-b]pyrazole derivatives, see: Vanotti et al. (1994 ▶); Kinnamon et al. (2000 ▶); Li et al. (2005 ▶). For bond-length data, see: Allen et al., 1987 ▶.

Experimental

Crystal data

C15H15N3O2S·H2O

M = 319.38

Orthorhombic,

a = 19.017 (2) Å

b = 5.4854 (7) Å

c = 15.2314 (18) Å

V = 1588.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 273 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.957, T max = 0.978

8763 measured reflections

3326 independent reflections

1877 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.094

S = 0.97

3326 reflections

207 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 1442 Friedel pairs

Flack parameter: −0.01 (9)

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010988/hg2495sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010988/hg2495Isup2.hkl

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

C15H15N3O2S·H2O	F(000) = 672
Mr = 319.38	Dx = 1.335 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1077 reflections
a = 19.017 (2) Å	θ = 2.5–18.0°
b = 5.4854 (7) Å	µ = 0.22 mm−1
c = 15.2314 (18) Å	T = 273 K
V = 1588.9 (3) Å3	Block, colorless
Z = 4	0.20 × 0.10 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	3326 independent reflections
Radiation source: fine-focus sealed tube	1877 reflections with I > 2σ(I)
graphite	Rint = 0.051
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→17
Tmin = 0.957, Tmax = 0.978	k = −7→6
8763 measured reflections	l = −19→19

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0345P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
3326 reflections	Δρmax = 0.15 e Å−3
207 parameters	Δρmin = −0.14 e Å−3
1 restraint	Absolute structure: Flack (1983), 1442 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (9)

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
S1	0.09788 (5)	−0.14517 (15)	0.84062 (6)	0.0691 (3)
O1	0.15780 (12)	0.2624 (4)	0.58697 (15)	0.0736 (7)
O2	0.09476 (11)	−0.0245 (4)	0.65679 (14)	0.0650 (6)
O3	0.2436 (2)	0.6611 (6)	0.55376 (16)	0.0945 (10)
H3A	0.275 (3)	0.647 (9)	0.502 (4)	0.16 (2)*
H3C	0.223 (3)	0.523 (10)	0.551 (3)	0.15 (2)*
N1	0.25532 (13)	0.5824 (4)	0.73178 (16)	0.0526 (7)
H1A	0.2568	0.6315	0.6782	0.063*
N2	0.22812 (12)	0.3832 (5)	0.84912 (16)	0.0525 (6)
N3	0.19001 (14)	0.2003 (5)	0.88960 (15)	0.0577 (7)
C1	0.34450 (18)	1.0192 (6)	0.7130 (2)	0.0603 (9)
H1B	0.3120	0.9869	0.6689	0.072*
C2	0.3920 (2)	1.2072 (6)	0.7024 (2)	0.0719 (11)
H2A	0.3909	1.3011	0.6516	0.086*
C3	0.4406 (2)	1.2562 (7)	0.7662 (3)	0.0738 (10)
H3B	0.4727	1.3824	0.7588	0.089*
C4	0.4416 (2)	1.1188 (7)	0.8405 (3)	0.0839 (10)
H4A	0.4748	1.1508	0.8838	0.101*
C5	0.39376 (19)	0.9320 (6)	0.8522 (3)	0.0759 (10)
H5A	0.3947	0.8413	0.9038	0.091*
C6	0.34440 (16)	0.8779 (6)	0.7882 (2)	0.0512 (8)
C7	0.29409 (17)	0.6804 (5)	0.8010 (2)	0.0527 (8)
C8	0.27674 (16)	0.5545 (6)	0.8748 (2)	0.0544 (9)
H8A	0.2942	0.5792	0.9312	0.065*
C9	0.21516 (17)	0.3985 (6)	0.76236 (19)	0.0490 (8)
C10	0.15369 (15)	0.1013 (5)	0.8233 (2)	0.0511 (8)
C11	0.16699 (17)	0.2151 (5)	0.7410 (2)	0.0502 (8)
C12	0.14107 (16)	0.1594 (6)	0.6547 (2)	0.0542 (8)
C13	0.0647 (2)	−0.1008 (7)	0.5744 (2)	0.0850 (12)
H13A	0.1009	−0.1654	0.5360	0.102*
H13B	0.0422	0.0358	0.5452	0.102*
C14	0.0120 (2)	−0.2929 (7)	0.5953 (3)	0.0986 (13)
H14A	−0.0095	−0.3494	0.5421	0.148*
H14B	−0.0235	−0.2265	0.6333	0.148*
H14C	0.0349	−0.4267	0.6242	0.148*
C15	0.1101 (2)	−0.1931 (7)	0.9562 (3)	0.0873 (13)
H15A	0.0816	−0.3276	0.9751	0.131*
H15B	0.0966	−0.0488	0.9876	0.131*
H15C	0.1587	−0.2285	0.9677	0.131*

	U11	U22	U33	U12	U13	U23
S1	0.0711 (6)	0.0678 (5)	0.0682 (6)	−0.0051 (5)	0.0093 (5)	0.0161 (5)
O1	0.0939 (19)	0.0829 (16)	0.0440 (12)	−0.0255 (15)	−0.0010 (14)	0.0096 (12)
O2	0.0703 (14)	0.0722 (15)	0.0526 (14)	−0.0146 (14)	−0.0035 (12)	0.0025 (12)
O3	0.131 (3)	0.107 (3)	0.0453 (15)	−0.041 (2)	0.0042 (15)	0.0143 (15)
N1	0.0628 (17)	0.0571 (16)	0.0377 (15)	0.0017 (14)	−0.0024 (13)	0.0054 (14)
N2	0.0642 (17)	0.0573 (16)	0.0359 (15)	0.0048 (13)	−0.0019 (14)	0.0087 (13)
N3	0.0700 (19)	0.0583 (16)	0.0448 (16)	−0.0010 (15)	0.0068 (15)	0.0150 (14)
C1	0.057 (2)	0.067 (2)	0.056 (2)	−0.0041 (19)	−0.0011 (16)	0.0014 (18)
C2	0.082 (3)	0.074 (3)	0.060 (2)	−0.006 (2)	0.013 (2)	0.007 (2)
C3	0.070 (2)	0.076 (2)	0.076 (3)	−0.015 (2)	0.010 (2)	−0.010 (2)
C4	0.089 (3)	0.088 (3)	0.075 (3)	−0.019 (2)	−0.015 (3)	−0.003 (3)
C5	0.088 (3)	0.077 (2)	0.062 (2)	−0.011 (2)	−0.018 (2)	0.006 (2)
C6	0.054 (2)	0.0534 (18)	0.046 (2)	0.0094 (16)	0.0014 (15)	−0.0006 (15)
C7	0.060 (2)	0.0549 (19)	0.0435 (19)	0.0042 (17)	−0.0012 (17)	0.0009 (17)
C8	0.062 (2)	0.060 (2)	0.0403 (18)	0.0040 (18)	−0.0048 (15)	0.0020 (16)
C9	0.0551 (19)	0.056 (2)	0.0365 (18)	0.0079 (17)	0.0028 (15)	0.0095 (16)
C10	0.0534 (19)	0.0508 (18)	0.049 (2)	0.0074 (15)	0.0022 (15)	0.0050 (16)
C11	0.057 (2)	0.054 (2)	0.0405 (17)	0.0023 (17)	0.0057 (16)	0.0049 (16)
C12	0.055 (2)	0.055 (2)	0.053 (2)	0.0005 (17)	0.0055 (17)	0.0062 (18)
C13	0.087 (3)	0.101 (3)	0.066 (3)	−0.026 (2)	−0.005 (2)	−0.011 (2)
C14	0.108 (3)	0.094 (3)	0.095 (3)	−0.043 (3)	0.001 (3)	−0.013 (2)
C15	0.107 (3)	0.089 (3)	0.067 (3)	−0.005 (2)	0.026 (2)	0.027 (2)

S1—C10	1.739 (3)	C3—H3B	0.9300
S1—C15	1.795 (4)	C4—C5	1.382 (4)
O1—C12	1.219 (4)	C4—H4A	0.9300
O2—C12	1.339 (3)	C5—C6	1.385 (4)
O2—C13	1.442 (4)	C5—H5A	0.9300
O3—H3A	0.99 (6)	C6—C7	1.459 (4)
O3—H3C	0.85 (6)	C7—C8	1.359 (4)
N1—C9	1.348 (3)	C8—H8A	0.9300
N1—C7	1.395 (4)	C9—C11	1.399 (4)
N1—H1A	0.8600	C10—C11	1.423 (4)
N2—C9	1.347 (4)	C11—C12	1.436 (4)
N2—C8	1.375 (4)	C13—C14	1.489 (5)
N2—N3	1.383 (3)	C13—H13A	0.9700
N3—C10	1.339 (4)	C13—H13B	0.9700
C1—C2	1.380 (4)	C14—H14A	0.9600
C1—C6	1.383 (4)	C14—H14B	0.9600
C1—H1B	0.9300	C14—H14C	0.9600
C2—C3	1.368 (5)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.360 (5)	C15—H15C	0.9600
Cg1···Cg2i	3.643 (2)
C10—S1—C15	100.60 (17)	C7—C8—H8A	127.0
C12—O2—C13	117.3 (3)	N2—C8—H8A	127.0
H3A—O3—H3C	99 (4)	N2—C9—N1	106.4 (3)
C9—N1—C7	109.0 (3)	N2—C9—C11	107.7 (3)
C9—N1—H1A	125.5	N1—C9—C11	146.0 (3)
C7—N1—H1A	125.5	N3—C10—C11	113.3 (3)
C9—N2—C8	111.1 (3)	N3—C10—S1	121.0 (2)
C9—N2—N3	112.8 (3)	C11—C10—S1	125.7 (2)
C8—N2—N3	136.2 (3)	C9—C11—C10	103.1 (3)
C10—N3—N2	103.2 (2)	C9—C11—C12	126.2 (3)
C2—C1—C6	121.1 (3)	C10—C11—C12	130.6 (3)
C2—C1—H1B	119.4	O1—C12—O2	122.7 (3)
C6—C1—H1B	119.4	O1—C12—C11	125.9 (3)
C3—C2—C1	120.4 (3)	O2—C12—C11	111.4 (3)
C3—C2—H2A	119.8	O2—C13—C14	106.6 (3)
C1—C2—H2A	119.8	O2—C13—H13A	110.4
C4—C3—C2	119.5 (4)	C14—C13—H13A	110.4
C4—C3—H3B	120.3	O2—C13—H13B	110.4
C2—C3—H3B	120.3	C14—C13—H13B	110.4
C3—C4—C5	120.6 (4)	H13A—C13—H13B	108.6
C3—C4—H4A	119.7	C13—C14—H14A	109.5
C5—C4—H4A	119.7	C13—C14—H14B	109.5
C4—C5—C6	120.9 (4)	H14A—C14—H14B	109.5
C4—C5—H5A	119.5	C13—C14—H14C	109.5
C6—C5—H5A	119.5	H14A—C14—H14C	109.5
C1—C6—C5	117.5 (3)	H14B—C14—H14C	109.5
C1—C6—C7	121.9 (3)	S1—C15—H15A	109.5
C5—C6—C7	120.6 (3)	S1—C15—H15B	109.5
C8—C7—N1	107.5 (3)	H15A—C15—H15B	109.5
C8—C7—C6	130.3 (3)	S1—C15—H15C	109.5
N1—C7—C6	122.1 (3)	H15A—C15—H15C	109.5
C7—C8—N2	106.0 (3)	H15B—C15—H15C	109.5
C9—N2—N3—C10	0.9 (3)	N3—N2—C9—C11	−1.2 (3)
C8—N2—N3—C10	−178.6 (3)	C7—N1—C9—N2	0.5 (3)
C6—C1—C2—C3	0.6 (5)	C7—N1—C9—C11	−177.5 (4)
C1—C2—C3—C4	−0.3 (5)	N2—N3—C10—C11	−0.2 (3)
C2—C3—C4—C5	−0.5 (6)	N2—N3—C10—S1	178.80 (19)
C3—C4—C5—C6	1.0 (6)	C15—S1—C10—N3	−0.8 (3)
C2—C1—C6—C5	−0.1 (5)	C15—S1—C10—C11	178.0 (3)
C2—C1—C6—C7	179.2 (3)	N2—C9—C11—C10	1.0 (3)
C4—C5—C6—C1	−0.7 (5)	N1—C9—C11—C10	179.0 (4)
C4—C5—C6—C7	179.9 (3)	N2—C9—C11—C12	−177.1 (3)
C9—N1—C7—C8	−0.4 (3)	N1—C9—C11—C12	0.9 (7)
C9—N1—C7—C6	178.0 (2)	N3—C10—C11—C9	−0.5 (3)
C1—C6—C7—C8	−165.9 (3)	S1—C10—C11—C9	−179.5 (2)
C5—C6—C7—C8	13.5 (5)	N3—C10—C11—C12	177.5 (3)
C1—C6—C7—N1	16.2 (4)	S1—C10—C11—C12	−1.4 (5)
C5—C6—C7—N1	−164.4 (3)	C13—O2—C12—O1	0.4 (4)
N1—C7—C8—N2	0.1 (3)	C13—O2—C12—C11	−179.7 (3)
C6—C7—C8—N2	−178.1 (3)	C9—C11—C12—O1	0.8 (5)
C9—N2—C8—C7	0.2 (3)	C10—C11—C12—O1	−176.9 (3)
N3—N2—C8—C7	179.7 (3)	C9—C11—C12—O2	−179.1 (3)
C8—N2—C9—N1	−0.5 (3)	C10—C11—C12—O2	3.2 (4)
N3—N2—C9—N1	179.9 (2)	C12—O2—C13—C14	−176.1 (3)
C8—N2—C9—C11	178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N3ii	0.99 (6)	1.86 (6)	2.809 (4)	160 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N3i	0.99 (6)	1.86 (6)	2.809 (4)	160 (5)

Symmetry code: (i) .