N-(4-Chloro-1,3-benzothia-zol-2-yl)-2-(3-methyl-phen-yl)acetamide monohydrate.

In the title compound, C(16)H(13)ClN(2)OS·H(2)O, the dihedral angle between the mean planes of the benzothia-zole ring system and the methylphenyl ring is 79.3 (6)°. The crystal packing features inter-molecular O-H⋯N, O-H⋯O and N-H⋯O hydrogen bonds involving the water mol-ecule and weak C-H⋯O, C-H⋯Cg and π-π stacking inter-actions [centroid-centroid distances = 3.8743 (7), 3.7229 (7) and 3.7076 (8) Å].

Related literature

For the biological activity of compounds with benzothia­zole skeletons, see: Aiello et al. (2008 ▶); Cho et al. (2008 ▶). For their structural similarity to the lateral chain of natural benzyl­penicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2006 ▶, 2008 ▶) and for their coordination abilities, see: Wu et al. (2008 ▶, 2010 ▶). For related structures, see: Davis & Healy (2010 ▶); John et al. (2010 ▶); Nogueira et al. (2010 ▶); Praveen et al. (2011 ▶); Selig et al. (2010 ▶); Wen et al. (2010 ▶); Xiao et al. (2010 ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C16H13ClN2OS·H2O

M = 334.81

Triclinic,

a = 7.2771 (3) Å

b = 9.2568 (5) Å

c = 12.0851 (5) Å

α = 83.948 (4)°

β = 84.306 (3)°

γ = 72.133 (4)°

V = 768.58 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.39 mm−1

T = 173 K

0.25 × 0.21 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.908, T max = 0.926

10307 measured reflections

4303 independent reflections

3834 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.089

S = 1.01

4303 reflections

209 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035872/im2316sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035872/im2316Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035872/im2316Isup3.cml

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

C16H13ClN2OS·H2O	Z = 2
Mr = 334.81	F(000) = 348
Triclinic, P1	Dx = 1.447 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2771 (3) Å	Cell parameters from 5935 reflections
b = 9.2568 (5) Å	θ = 3.2–32.2°
c = 12.0851 (5) Å	µ = 0.39 mm−1
α = 83.948 (4)°	T = 173 K
β = 84.306 (3)°	Block, colorless
γ = 72.133 (4)°	0.25 × 0.21 × 0.20 mm
V = 768.58 (6) Å3

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4303 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3834 reflections with I > 2σ(I)
graphite	Rint = 0.013
Detector resolution: 16.1500 pixels mm-1	θmax = 29.6°, θmin = 3.2°
ω scans	h = −6→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −12→12
Tmin = 0.908, Tmax = 0.926	l = −16→16
10307 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.2662P] where P = (Fo2 + 2Fc2)/3
4303 reflections	(Δ/σ)max = 0.007
209 parameters	Δρmax = 0.40 e Å−3
4 restraints	Δρmin = −0.28 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.10411 (4)	0.65402 (3)	0.47845 (2)	0.02017 (8)
Cl1	0.78434 (4)	0.64763 (4)	0.28146 (3)	0.02807 (9)
O1	−0.10370 (13)	0.84965 (11)	0.62242 (8)	0.02685 (19)
O2	0.47923 (14)	0.98584 (11)	0.64369 (9)	0.0289 (2)
H2OB	0.477 (2)	1.0762 (16)	0.6127 (14)	0.035*
H2OA	0.600 (2)	0.9272 (17)	0.6380 (15)	0.035*
N1	0.41640 (14)	0.74054 (11)	0.44287 (8)	0.01894 (19)
N2	0.19872 (14)	0.86818 (11)	0.58166 (8)	0.01959 (19)
H2N	0.285 (2)	0.9074 (18)	0.5985 (13)	0.024*
C1	0.43805 (16)	0.62472 (13)	0.37390 (9)	0.0181 (2)
C2	0.59653 (16)	0.56742 (13)	0.29843 (10)	0.0202 (2)
C3	0.60131 (18)	0.44952 (14)	0.23612 (11)	0.0242 (2)
H3A	0.7097	0.4102	0.1856	0.029*
C4	0.44702 (19)	0.38796 (14)	0.24728 (11)	0.0263 (3)
H4A	0.4525	0.3063	0.2043	0.032*
C5	0.28611 (18)	0.44326 (14)	0.31952 (11)	0.0237 (2)
H5A	0.1808	0.4018	0.3261	0.028*
C6	0.28419 (17)	0.56185 (13)	0.38211 (9)	0.0195 (2)
C7	0.25131 (16)	0.76327 (13)	0.50223 (9)	0.0179 (2)
C8	0.02371 (17)	0.90296 (13)	0.64119 (10)	0.0200 (2)
C9	0.00054 (18)	1.00506 (14)	0.73487 (10)	0.0224 (2)
H9A	−0.1334	1.0745	0.7408	0.027*
H9B	0.0903	1.0675	0.7194	0.027*
C10	0.04473 (18)	0.90619 (14)	0.84323 (10)	0.0219 (2)
C11	0.20475 (18)	0.90263 (15)	0.89814 (10)	0.0246 (2)
H11A	0.2826	0.9654	0.8689	0.030*
C12	0.2537 (2)	0.80858 (16)	0.99563 (11)	0.0303 (3)
C13	0.1374 (2)	0.71844 (17)	1.03722 (12)	0.0348 (3)
H13A	0.1688	0.6535	1.1033	0.042*
C14	−0.0235 (2)	0.72173 (17)	0.98378 (12)	0.0347 (3)
H14A	−0.1020	0.6597	1.0137	0.042*
C15	−0.0708 (2)	0.81538 (16)	0.88651 (11)	0.0287 (3)
H15A	−0.1813	0.8174	0.8498	0.034*
C20	0.4298 (2)	0.8049 (2)	1.05269 (14)	0.0455 (4)
H20A	0.5070	0.6990	1.0692	0.068*
H20B	0.3894	0.8551	1.1224	0.068*
H20C	0.5076	0.8584	1.0037	0.068*

	U11	U22	U33	U12	U13	U23
S1	0.01938 (14)	0.02259 (14)	0.02136 (14)	−0.01061 (11)	0.00229 (10)	−0.00472 (10)
Cl1	0.02011 (15)	0.03273 (17)	0.03346 (17)	−0.01163 (12)	0.00420 (11)	−0.00644 (12)
O1	0.0204 (4)	0.0311 (5)	0.0311 (5)	−0.0101 (4)	0.0026 (3)	−0.0085 (4)
O2	0.0231 (4)	0.0243 (4)	0.0412 (5)	−0.0111 (4)	0.0024 (4)	−0.0034 (4)
N1	0.0190 (4)	0.0195 (4)	0.0197 (4)	−0.0079 (4)	0.0003 (3)	−0.0030 (4)
N2	0.0192 (5)	0.0215 (5)	0.0203 (4)	−0.0089 (4)	0.0008 (4)	−0.0049 (4)
C1	0.0190 (5)	0.0172 (5)	0.0181 (5)	−0.0056 (4)	−0.0012 (4)	−0.0004 (4)
C2	0.0175 (5)	0.0202 (5)	0.0221 (5)	−0.0054 (4)	−0.0003 (4)	−0.0004 (4)
C3	0.0225 (6)	0.0219 (5)	0.0260 (6)	−0.0035 (4)	0.0021 (4)	−0.0055 (4)
C4	0.0288 (6)	0.0209 (5)	0.0293 (6)	−0.0066 (5)	0.0007 (5)	−0.0081 (5)
C5	0.0247 (6)	0.0220 (5)	0.0269 (6)	−0.0103 (5)	0.0003 (4)	−0.0052 (4)
C6	0.0197 (5)	0.0193 (5)	0.0199 (5)	−0.0069 (4)	0.0005 (4)	−0.0017 (4)
C7	0.0189 (5)	0.0181 (5)	0.0177 (5)	−0.0074 (4)	−0.0013 (4)	−0.0009 (4)
C8	0.0206 (5)	0.0181 (5)	0.0200 (5)	−0.0045 (4)	−0.0007 (4)	−0.0005 (4)
C9	0.0256 (6)	0.0188 (5)	0.0213 (5)	−0.0046 (4)	0.0018 (4)	−0.0039 (4)
C10	0.0235 (5)	0.0200 (5)	0.0197 (5)	−0.0034 (4)	0.0041 (4)	−0.0048 (4)
C11	0.0240 (6)	0.0243 (6)	0.0235 (5)	−0.0047 (5)	0.0032 (4)	−0.0052 (4)
C12	0.0282 (6)	0.0319 (7)	0.0245 (6)	−0.0002 (5)	0.0015 (5)	−0.0032 (5)
C13	0.0387 (8)	0.0317 (7)	0.0259 (6)	−0.0027 (6)	0.0045 (5)	0.0040 (5)
C14	0.0375 (8)	0.0315 (7)	0.0327 (7)	−0.0120 (6)	0.0100 (6)	0.0018 (5)
C15	0.0274 (6)	0.0299 (6)	0.0284 (6)	−0.0096 (5)	0.0044 (5)	−0.0032 (5)
C20	0.0377 (8)	0.0574 (11)	0.0365 (8)	−0.0071 (8)	−0.0108 (6)	0.0042 (7)

S1—C6	1.7382 (12)	C5—H5A	0.9500
S1—C7	1.7436 (12)	C8—C9	1.5144 (16)
Cl1—C2	1.7310 (12)	C9—C10	1.5186 (17)
O1—C8	1.2250 (15)	C9—H9A	0.9900
O2—H2OB	0.876 (13)	C9—H9B	0.9900
O2—H2OA	0.883 (13)	C10—C11	1.3866 (18)
N1—C7	1.3068 (15)	C10—C15	1.3934 (18)
N1—C1	1.3884 (14)	C11—C12	1.3963 (18)
N2—C8	1.3633 (15)	C11—H11A	0.9500
N2—C7	1.3809 (14)	C12—C13	1.387 (2)
N2—H2N	0.868 (13)	C12—C20	1.504 (2)
C1—C2	1.4004 (15)	C13—C14	1.383 (2)
C1—C6	1.4028 (16)	C13—H13A	0.9500
C2—C3	1.3799 (17)	C14—C15	1.391 (2)
C3—C4	1.3964 (18)	C14—H14A	0.9500
C3—H3A	0.9500	C15—H15A	0.9500
C4—C5	1.3853 (17)	C20—H20A	0.9800
C4—H4A	0.9500	C20—H20B	0.9800
C5—C6	1.3932 (16)	C20—H20C	0.9800
C6—S1—C7	88.18 (5)	C8—C9—C10	108.76 (10)
H2OB—O2—H2OA	107.2 (14)	C8—C9—H9A	109.9
C7—N1—C1	109.19 (10)	C10—C9—H9A	109.9
C8—N2—C7	123.21 (10)	C8—C9—H9B	109.9
C8—N2—H2N	118.6 (10)	C10—C9—H9B	109.9
C7—N2—H2N	118.0 (11)	H9A—C9—H9B	108.3
N1—C1—C2	126.10 (11)	C11—C10—C15	119.52 (12)
N1—C1—C6	115.52 (10)	C11—C10—C9	119.83 (11)
C2—C1—C6	118.38 (11)	C15—C10—C9	120.63 (12)
C3—C2—C1	120.19 (11)	C10—C11—C12	121.27 (13)
C3—C2—Cl1	120.05 (9)	C10—C11—H11A	119.4
C1—C2—Cl1	119.75 (9)	C12—C11—H11A	119.4
C2—C3—C4	120.06 (11)	C13—C12—C11	118.40 (14)
C2—C3—H3A	120.0	C13—C12—C20	121.33 (14)
C4—C3—H3A	120.0	C11—C12—C20	120.26 (14)
C5—C4—C3	121.51 (11)	C14—C13—C12	120.94 (13)
C5—C4—H4A	119.2	C14—C13—H13A	119.5
C3—C4—H4A	119.2	C12—C13—H13A	119.5
C4—C5—C6	117.62 (11)	C13—C14—C15	120.30 (14)
C4—C5—H5A	121.2	C13—C14—H14A	119.8
C6—C5—H5A	121.2	C15—C14—H14A	119.8
C5—C6—C1	122.21 (11)	C14—C15—C10	119.57 (13)
C5—C6—S1	128.07 (9)	C14—C15—H15A	120.2
C1—C6—S1	109.71 (8)	C10—C15—H15A	120.2
N1—C7—N2	120.77 (10)	C12—C20—H20A	109.5
N1—C7—S1	117.35 (9)	C12—C20—H20B	109.5
N2—C7—S1	121.88 (8)	H20A—C20—H20B	109.5
O1—C8—N2	121.69 (11)	C12—C20—H20C	109.5
O1—C8—C9	122.33 (11)	H20A—C20—H20C	109.5
N2—C8—C9	115.92 (10)	H20B—C20—H20C	109.5
C7—N1—C1—C2	−179.68 (11)	C8—N2—C7—N1	175.97 (11)
C7—N1—C1—C6	0.58 (14)	C8—N2—C7—S1	−5.13 (16)
N1—C1—C2—C3	178.77 (11)	C6—S1—C7—N1	2.23 (10)
C6—C1—C2—C3	−1.50 (17)	C6—S1—C7—N2	−176.71 (10)
N1—C1—C2—Cl1	−2.55 (17)	C7—N2—C8—O1	−4.83 (18)
C6—C1—C2—Cl1	177.18 (9)	C7—N2—C8—C9	172.42 (10)
C1—C2—C3—C4	0.67 (19)	O1—C8—C9—C10	81.73 (14)
Cl1—C2—C3—C4	−178.01 (10)	N2—C8—C9—C10	−95.49 (12)
C2—C3—C4—C5	0.5 (2)	C8—C9—C10—C11	114.28 (12)
C3—C4—C5—C6	−0.8 (2)	C8—C9—C10—C15	−63.84 (14)
C4—C5—C6—C1	−0.11 (19)	C15—C10—C11—C12	0.61 (18)
C4—C5—C6—S1	179.87 (10)	C9—C10—C11—C12	−177.53 (11)
N1—C1—C6—C5	−179.00 (11)	C10—C11—C12—C13	−0.31 (19)
C2—C1—C6—C5	1.24 (18)	C10—C11—C12—C20	179.05 (13)
N1—C1—C6—S1	1.01 (13)	C11—C12—C13—C14	−0.2 (2)
C2—C1—C6—S1	−178.75 (9)	C20—C12—C13—C14	−179.55 (14)
C7—S1—C6—C5	178.34 (12)	C12—C13—C14—C15	0.4 (2)
C7—S1—C6—C1	−1.67 (9)	C13—C14—C15—C10	−0.1 (2)
C1—N1—C7—N2	176.95 (10)	C11—C10—C15—C14	−0.39 (19)
C1—N1—C7—S1	−2.00 (13)	C9—C10—C15—C14	177.73 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2OB···N1i	0.88 (1)	2.10 (2)	2.924 (1)	158 (2)
O2—H2OA···O1ii	0.88 (1)	2.05 (1)	2.904 (1)	164 (2)
N2—H2N···O2	0.87 (1)	1.92 (1)	2.785 (1)	177 (2)
C5—H5A···O1iii	0.95	2.56	3.351 (2)	141.
C3—H3A···Cg3iv	0.95	2.66	3.502 (1)	148

CgI···CgJ	CgI···CgJ (Å)	CgI···Perp (Å)	CgJ···Perp (Å)
Cg1···Cg1i	3.8743 (7)	3.5381 (4)	3.581 (4)
Cg1···Cg2i	3.7229 (7)	3.5474 (4)	3.5229 (5)
Cg3···Cg3ii	3.7076 (8)	3.4878 (6)	3.4878 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2OB⋯N1i	0.88 (1)	2.10 (2)	2.924 (1)	158 (2)
O2—H2OA⋯O1ii	0.88 (1)	2.05 (1)	2.904 (1)	164 (2)
N2—H2N⋯O2	0.87 (1)	1.92 (1)	2.785 (1)	177 (2)
C5—H5A⋯O1iii	0.95	2.56	3.351 (2)	141
C3—H3A⋯Cg3iv	0.95	2.66	3.502 (1)	148

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