Ethyl 2-{(2Z)-2-[(1-naphthyl-sulfon-yl)imino]-2,3-dihydro-1,3-thia-zol-4-yl}acetate monohydrate.

The title compound, C(17)H(16)N(2)O(4)S(2)·H(2)O, is of inter-est with respect to its anti-diabetic and anti-obesity activity. In the crystal, the packing is stabilized by three cooperative inter-actions: offset π-π inter-actions [centroid-centroid distance = 3.604 (2) Å], as well as C-H⋯O and O-H⋯O hydrogen bonds. N-H⋯O inter-actions also occur.

Related literature

For similar structures and their anti­diabetic activity, see: Navarrete-Vázquez et al. (2008 ▶); Alberts et al. (2002 ▶); Barf et al. (2002 ▶); Fotsch & Wang (2008 ▶); Saiah (2008 ▶); Vicker et al. (2007 ▶). For hydrogen bonds, see: Adams et al. (1996 ▶); Desiraju & Steiner (1999 ▶); Hanton et al. (1992 ▶).

Experimental

Crystal data

C17H16N2O4S2·H2O

M = 394.45

Orthorhombic,

a = 29.582 (6) Å

b = 7.9657 (17) Å

c = 15.676 (3) Å

V = 3694.0 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 273 K

0.29 × 0.21 × 0.17 mm

Data collection

Bruker SMART APEX CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.913, T max = 0.948

33131 measured reflections

3255 independent reflections

2488 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.143

S = 1.09

3255 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus-NT (Bruker, 2001 ▶); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: PLATON (Spek, 2009 ▶), DIAMOND (Bergerhoff et al., 1996 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039279/jh2215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039279/jh2215Isup2.hkl

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

C17H16N2O4S2·H2O	Dx = 1.419 Mg m−3
Mr = 394.45	Melting point: 371 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 7399 reflections
a = 29.582 (6) Å	θ = 2.6–23.6°
b = 7.9657 (17) Å	µ = 0.32 mm−1
c = 15.676 (3) Å	T = 273 K
V = 3694.0 (14) Å3	Rectangular prism, colourless
Z = 8	0.29 × 0.21 × 0.17 mm
F(000) = 1648

Bruker SMART APEX CCD area detector diffractometer	3255 independent reflections
Radiation source: fine-focus sealed tube	2488 reflections with I > 2σ(I)
graphite	Rint = 0.056
Detector resolution: 8.3 pixels mm-1	θmax = 25.0°, θmin = 1.4°
phi and ω scans	h = −35→35
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
Tmin = 0.913, Tmax = 0.948	l = −18→18
33131 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0753P)2 + 1.2945P] where P = (Fo2 + 2Fc2)/3
3255 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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	0.30111 (9)	1.0099 (3)	−0.01807 (17)	0.0476 (7)
C2	0.27124 (10)	1.0650 (4)	0.0426 (2)	0.0579 (8)
H2	0.2818	1.1180	0.0915	0.069*
C3	0.22466 (11)	1.0411 (4)	0.0306 (3)	0.0694 (9)
H3	0.2044	1.0776	0.0719	0.083*
C4	0.20921 (10)	0.9652 (4)	−0.0408 (2)	0.0679 (9)
H4	0.1782	0.9534	−0.0487	0.081*
C5	0.23901 (10)	0.9033 (4)	−0.1037 (2)	0.0562 (8)
C6	0.22292 (12)	0.8195 (5)	−0.1765 (2)	0.0724 (10)
H6	0.1919	0.8057	−0.1838	0.087*
C7	0.25155 (14)	0.7585 (5)	−0.2363 (2)	0.0794 (11)
H7	0.2402	0.7041	−0.2842	0.095*
C8	0.29822 (13)	0.7776 (5)	−0.2257 (2)	0.0733 (9)
H8	0.3178	0.7355	−0.2669	0.088*
C9	0.31544 (11)	0.8571 (4)	−0.15595 (18)	0.0573 (7)
H9	0.3466	0.8675	−0.1499	0.069*
C10	0.28653 (9)	0.9240 (3)	−0.09264 (18)	0.0484 (7)
C11	0.38848 (8)	0.8134 (3)	0.08417 (17)	0.0433 (6)
C12	0.40857 (8)	0.5962 (3)	0.17449 (16)	0.0436 (6)
C13	0.39714 (10)	0.7109 (4)	0.23161 (18)	0.0557 (7)
H13	0.3984	0.6930	0.2902	0.067*
C14	0.42320 (9)	0.4204 (3)	0.18915 (18)	0.0496 (7)
H14A	0.4013	0.3457	0.1630	0.060*
H14B	0.4230	0.3986	0.2500	0.060*
C15	0.46919 (9)	0.3790 (4)	0.15489 (18)	0.0508 (7)
C16	0.51735 (11)	0.1490 (5)	0.1211 (3)	0.0821 (11)
H16A	0.5425	0.1802	0.1575	0.099*
H16B	0.5228	0.1929	0.0643	0.099*
C17	0.51244 (15)	−0.0349 (5)	0.1183 (3)	0.1036 (14)
H17A	0.5089	−0.0774	0.1752	0.155*
H17B	0.5389	−0.0835	0.0928	0.155*
H17C	0.4863	−0.0637	0.0850	0.155*
N1	0.38373 (7)	0.8826 (3)	0.00845 (14)	0.0499 (6)
N2	0.40331 (7)	0.6559 (3)	0.09207 (13)	0.0428 (5)
H2A	0.4093	0.5947	0.0483	0.051*
O1	0.36124 (7)	1.1601 (2)	0.07509 (14)	0.0648 (6)
O2	0.37576 (7)	1.1370 (3)	−0.07715 (14)	0.0639 (6)
O3	0.49668 (8)	0.4789 (3)	0.13212 (19)	0.0858 (8)
O4	0.47548 (7)	0.2156 (3)	0.15495 (15)	0.0698 (6)
O5	0.57738 (8)	0.5513 (3)	0.04480 (16)	0.0876 (8)
H5A	0.5842	0.6535	0.0484	0.131*
H5B	0.5518	0.5450	0.0679	0.131*
S1	0.35869 (2)	1.05939 (9)	−0.00081 (5)	0.0514 (2)
S2	0.37963 (3)	0.89724 (10)	0.18608 (5)	0.0577 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0426 (14)	0.0430 (14)	0.0572 (16)	−0.0020 (12)	−0.0018 (12)	0.0115 (13)
C2	0.0547 (18)	0.0499 (17)	0.0692 (19)	0.0008 (13)	0.0047 (15)	0.0069 (15)
C3	0.0510 (18)	0.063 (2)	0.094 (3)	0.0032 (15)	0.0181 (18)	0.0091 (19)
C4	0.0385 (15)	0.067 (2)	0.098 (3)	−0.0065 (14)	0.0017 (17)	0.023 (2)
C5	0.0482 (17)	0.0538 (17)	0.0665 (18)	−0.0140 (13)	−0.0068 (14)	0.0201 (15)
C6	0.062 (2)	0.074 (2)	0.082 (2)	−0.0258 (18)	−0.0198 (19)	0.026 (2)
C7	0.097 (3)	0.078 (2)	0.063 (2)	−0.034 (2)	−0.019 (2)	0.0146 (19)
C8	0.087 (3)	0.075 (2)	0.058 (2)	−0.0155 (19)	0.0034 (18)	0.0084 (17)
C9	0.0561 (17)	0.0624 (19)	0.0534 (17)	−0.0079 (14)	0.0026 (14)	0.0120 (15)
C10	0.0447 (15)	0.0450 (15)	0.0555 (16)	−0.0063 (12)	−0.0026 (13)	0.0184 (13)
C11	0.0314 (12)	0.0479 (15)	0.0505 (16)	−0.0008 (11)	−0.0009 (11)	−0.0038 (12)
C12	0.0347 (13)	0.0540 (17)	0.0422 (14)	0.0008 (11)	0.0002 (11)	0.0044 (12)
C13	0.0617 (17)	0.0663 (19)	0.0391 (15)	0.0072 (15)	0.0040 (13)	0.0001 (14)
C14	0.0413 (15)	0.0563 (17)	0.0512 (16)	0.0022 (12)	0.0036 (12)	0.0065 (13)
C15	0.0423 (15)	0.0605 (19)	0.0494 (16)	0.0001 (14)	−0.0031 (12)	−0.0024 (14)
C16	0.0498 (18)	0.092 (3)	0.105 (3)	0.0127 (17)	0.0076 (18)	−0.036 (2)
C17	0.088 (3)	0.086 (3)	0.137 (4)	0.028 (2)	0.028 (3)	−0.019 (3)
N1	0.0469 (13)	0.0547 (14)	0.0480 (13)	0.0037 (11)	−0.0023 (10)	0.0069 (11)
N2	0.0409 (12)	0.0480 (13)	0.0395 (11)	0.0024 (10)	0.0001 (9)	−0.0034 (9)
O1	0.0653 (14)	0.0492 (12)	0.0798 (15)	0.0002 (9)	−0.0171 (11)	−0.0087 (11)
O2	0.0493 (11)	0.0649 (13)	0.0774 (14)	−0.0120 (10)	−0.0017 (10)	0.0266 (11)
O3	0.0549 (13)	0.0784 (16)	0.124 (2)	−0.0084 (13)	0.0285 (13)	−0.0052 (15)
O4	0.0510 (12)	0.0629 (14)	0.0955 (17)	0.0114 (10)	0.0146 (11)	−0.0053 (12)
O5	0.0865 (17)	0.0755 (16)	0.1008 (18)	−0.0314 (13)	0.0476 (14)	−0.0389 (14)
S1	0.0429 (4)	0.0474 (4)	0.0641 (5)	−0.0047 (3)	−0.0060 (3)	0.0101 (3)
S2	0.0665 (5)	0.0547 (5)	0.0520 (4)	0.0092 (4)	0.0064 (3)	−0.0083 (3)

C1—C2	1.370 (4)	C12—N2	1.385 (3)
C1—C10	1.421 (4)	C12—C14	1.484 (4)
C1—S1	1.769 (3)	C13—S2	1.727 (3)
C2—C3	1.404 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.499 (4)
C3—C4	1.352 (5)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.411 (5)	C15—O3	1.193 (3)
C4—H4	0.9300	C15—O4	1.315 (3)
C5—C6	1.406 (4)	C16—O4	1.448 (4)
C5—C10	1.426 (4)	C16—C17	1.473 (5)
C6—C7	1.353 (5)	C16—H16A	0.9700
C6—H6	0.9300	C16—H16B	0.9700
C7—C8	1.399 (5)	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C8—C9	1.363 (4)	C17—H17C	0.9600
C8—H8	0.9300	N1—S1	1.598 (2)
C9—C10	1.414 (4)	N2—H2A	0.8600
C9—H9	0.9300	O1—S1	1.437 (2)
C11—N1	1.316 (3)	O2—S1	1.439 (2)
C11—N2	1.335 (3)	O5—H5A	0.8399
C11—S2	1.751 (3)	O5—H5B	0.8400
C12—C13	1.323 (4)
C2—C1—C10	121.9 (3)	C12—C13—H13	123.5
C2—C1—S1	116.3 (2)	S2—C13—H13	123.5
C10—C1—S1	121.7 (2)	C12—C14—C15	114.6 (2)
C1—C2—C3	119.8 (3)	C12—C14—H14A	108.6
C1—C2—H2	120.1	C15—C14—H14A	108.6
C3—C2—H2	120.1	C12—C14—H14B	108.6
C4—C3—C2	120.2 (3)	C15—C14—H14B	108.6
C4—C3—H3	119.9	H14A—C14—H14B	107.6
C2—C3—H3	119.9	O3—C15—O4	124.4 (3)
C3—C4—C5	121.5 (3)	O3—C15—C14	125.4 (3)
C3—C4—H4	119.2	O4—C15—C14	110.2 (2)
C5—C4—H4	119.2	O4—C16—C17	106.9 (3)
C6—C5—C4	121.4 (3)	O4—C16—H16A	110.3
C6—C5—C10	119.2 (3)	C17—C16—H16A	110.3
C4—C5—C10	119.4 (3)	O4—C16—H16B	110.3
C7—C6—C5	121.4 (3)	C17—C16—H16B	110.3
C7—C6—H6	119.3	H16A—C16—H16B	108.6
C5—C6—H6	119.3	C16—C17—H17A	109.5
C6—C7—C8	119.8 (3)	C16—C17—H17B	109.5
C6—C7—H7	120.1	H17A—C17—H17B	109.5
C8—C7—H7	120.1	C16—C17—H17C	109.5
C9—C8—C7	120.9 (3)	H17A—C17—H17C	109.5
C9—C8—H8	119.5	H17B—C17—H17C	109.5
C7—C8—H8	119.5	C11—N1—S1	120.0 (2)
C8—C9—C10	120.8 (3)	C11—N2—C12	116.5 (2)
C8—C9—H9	119.6	C11—N2—H2A	121.8
C10—C9—H9	119.6	C12—N2—H2A	121.8
C9—C10—C1	125.1 (3)	C15—O4—C16	118.9 (3)
C9—C10—C5	117.9 (3)	H5A—O5—H5B	104.1
C1—C10—C5	117.0 (3)	O1—S1—O2	115.50 (13)
N1—C11—N2	120.8 (2)	O1—S1—N1	113.12 (12)
N1—C11—S2	130.3 (2)	O2—S1—N1	106.95 (13)
N2—C11—S2	108.83 (19)	O1—S1—C1	107.55 (13)
C13—C12—N2	111.4 (2)	O2—S1—C1	107.85 (13)
C13—C12—C14	128.4 (2)	N1—S1—C1	105.29 (12)
N2—C12—C14	120.1 (2)	C13—S2—C11	90.25 (13)
C12—C13—S2	113.0 (2)
C10—C1—C2—C3	−1.8 (4)	N2—C12—C14—C15	62.3 (3)
S1—C1—C2—C3	175.5 (2)	C12—C14—C15—O3	14.1 (4)
C1—C2—C3—C4	−0.5 (5)	C12—C14—C15—O4	−167.2 (2)
C2—C3—C4—C5	2.1 (5)	N2—C11—N1—S1	170.26 (19)
C3—C4—C5—C6	177.9 (3)	S2—C11—N1—S1	−11.7 (3)
C3—C4—C5—C10	−1.3 (4)	N1—C11—N2—C12	178.0 (2)
C4—C5—C6—C7	−179.3 (3)	S2—C11—N2—C12	−0.4 (3)
C10—C5—C6—C7	−0.1 (5)	C13—C12—N2—C11	0.4 (3)
C5—C6—C7—C8	0.4 (5)	C14—C12—N2—C11	177.6 (2)
C6—C7—C8—C9	0.0 (5)	O3—C15—O4—C16	−3.5 (5)
C7—C8—C9—C10	−0.7 (5)	C14—C15—O4—C16	177.7 (3)
C8—C9—C10—C1	−179.5 (3)	C17—C16—O4—C15	−172.3 (3)
C8—C9—C10—C5	0.9 (4)	C11—N1—S1—O1	26.1 (3)
C2—C1—C10—C9	−177.0 (3)	C11—N1—S1—O2	154.4 (2)
S1—C1—C10—C9	5.7 (4)	C11—N1—S1—C1	−91.0 (2)
C2—C1—C10—C5	2.5 (4)	C2—C1—S1—O1	−3.2 (2)
S1—C1—C10—C5	−174.7 (2)	C10—C1—S1—O1	174.1 (2)
C6—C5—C10—C9	−0.5 (4)	C2—C1—S1—O2	−128.4 (2)
C4—C5—C10—C9	178.6 (3)	C10—C1—S1—O2	48.9 (2)
C6—C5—C10—C1	179.9 (3)	C2—C1—S1—N1	117.7 (2)
C4—C5—C10—C1	−1.0 (4)	C10—C1—S1—N1	−65.0 (2)
N2—C12—C13—S2	−0.2 (3)	C12—C13—S2—C11	0.0 (2)
C14—C12—C13—S2	−177.1 (2)	N1—C11—S2—C13	−177.9 (3)
C13—C12—C14—C15	−121.0 (3)	N2—C11—S2—C13	0.27 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5i	0.86	1.91	2.767 (3)	177
O5—H5A···O2ii	0.84	2.10	2.889 (3)	157
C13—H13···O2iii	0.93	2.57	3.295 (4)	135
C14—H14A···O1iv	0.97	2.34	3.295 (3)	167
C17—H17B···O2i	0.96	2.57	3.466 (5)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5i	0.86	1.91	2.767 (3)	177
O5—H5A⋯O2ii	0.84	2.10	2.889 (3)	157
C13—H13⋯O2iii	0.93	2.57	3.295 (4)	135
C14—H14A⋯O1iv	0.97	2.34	3.295 (3)	167
C17—H17B⋯O2i	0.96	2.57	3.466 (5)	155

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