N-(4-Chloro-1,3-benzothia­zol-2-yl)-2-(3-methyl­phen­yl)acetamide monohydrate

Praveen, A.S.; Jasinski, J.P.; Golen, J.A.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536811035872

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Pages o2602-o2603

https://doi.org/10.1107/S1600536811035872

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N-(4-Chloro-1,3-benzothiazol-2-yl)-2-(3-methylphenyl)acetamide monohydrate

A. S. Praveen,^a Jerry P. Jasinski,^b ^* James A. Golen,^b H. S. Yathirajan ^a and B. Narayana ^c

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 30 August 2011; accepted 2 September 2011; online 14 September 2011)

In the title compound, C₁₆H₁₃ClN₂OS·H₂O, the dihedral angle between the mean planes of the benzothiazole ring system and the methylphenyl ring is 79.3 (6)°. The crystal packing features intermolecular O—H⋯N, O—H⋯O and N—H⋯O hydrogen bonds involving the water molecule and weak C—H⋯O, C—H⋯Cg and π–π stacking interactions [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_r = 334.81
Triclinic, $[P \overline 1]$
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 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.089
S = 1.01
4303 reflections
209 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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⋯Cg3^iv	0.95	2.66	3.502 (1)	148
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x+1, y, z; (iii) -x, -y+1, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811035872/im2316sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035872/im2316Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035872/im2316Isup3.cml

checkCIF report

Comment top

The biological activity of compounds with benzothiazole skeletons includes anticancer, antibacterial, antifungal and anthelmintic properties (Aiello et al., 2008; Cho et al., 2008) N-Substituted 2-arylacetamides are very interesting compounds because of their structural similarity to the lateral chain of natural benzylpenicillin (Mijin et al., 2008; Mijin et al., 2006). Amides are also used as ligands due to their excellent coordination abilities (Wu et al., 2008; 2010). Crystal structures of some acetamidederivatives, viz., 2-(4-bromophenyl)-N-(2-methoxyphenyl)acetamide (Xiao et al., 2010), N-benzyl-2-(3-chloro-4-hydroxyphenyl)acetamide (Davis et al., 2010), 2-[(5,7-dibromoquinolin-8-yl)oxy]-N-(2-methoxyphenyl)acetamide (Wen et al., 2010), N-(4-bromophenyl)-2-(2-thienyl)acetamide (Nogueira et al., 2010), N-[4-(benzylsulfamoyl)phenyl]acetamide (John et al., 2010), 2-(4-fluorophenyl)-N-{4-[6-(4-fluorophenyl)-2,3-dihydroimidazo[2,1-b][1,3] thiazol-5-yl]pyridin-2-yl}acetamide (Selig et al., 2010) and N-(3-chloro-4-fluorophenyl)-2-(naphthalen-1-yl)acetamide (Praveen et al., 2011) have been reported. As part of our ongoing studies of amides, the title compound is synthesized and its crystal structure is reported.

In the title hydrated compound, C₁₆H₁₃ClN₂OS × H₂O, the dihedral angle between the mean planes of the benzothiazole and benzenes is 79.3 (6)° (Fig. 1). Crystal packing is realized by O–H···N, O—H···O and N—H···O hydrogen bonds involving the water molecule and weak O—H···O, C—H···O, C—H···Cg (Table 1) and π–π stacking (Table 2) intermolecular interactions (Fig. 2).

Related literature top

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 top

To a stirred solution of (3-methylphenyl)acetic acid (1 g, 6.65 mmol), triethylamine (1.34 g, 13.31 mmol) and 4-chloro-1,3-benzothiazol-2-amine (1.27 g, 6.65 mmol) in dichloromethane (10 ml), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCl (1.52 g, 7.93 mmol) was added at 273 K. The reaction mixture was stirred at room temperature for 3 h. After the completion of the reaction, the reaction mixture was poured into ice cold water and the layers were separated. The organic layer was washed with 10% aq. NaHCO₃ solution (10 ml), brine (10 ml), dried over anhydrous Na₂SO₄, filtered and concentrated under vacuum to obtain the crude product which was triturated with ethanol and filtered to afford 1.92 g of the title compound (I) as a white solid in 91 % yield. Single crystals were grown from ethanol by slow evaporation method (m.p.: 397-398 K).

Structure description top

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).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme and 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed down the a axis. Dashed lines indicate O—H···N hydrogen bonds.

N-(4-Chloro-1,3-benzothiazol-2-yl)-2-(3-methylphenyl)acetamide monohydrate top

Crystal data top

C₁₆H₁₃ClN₂OS·H₂O	Z = 2
M_r = 334.81	F(000) = 348
Triclinic, P1	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4303 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3834 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
Detector resolution: 16.1500 pixels mm^-1	θ_max = 29.6°, θ_min = 3.2°
ω scans	h = −6→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −12→12
T_min = 0.908, T_max = 0.926	l = −16→16
10307 measured reflections

Refinement top

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(F_o²) + (0.0502P)² + 0.2662P] where P = (F_o² + 2F_c²)/3
4303 reflections	(Δ/σ)_max = 0.007
209 parameters	Δρ_max = 0.40 e Å⁻³
4 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₃ClN₂OS·H₂O	γ = 72.133 (4)°
M_r = 334.81	V = 768.58 (6) Å³
Triclinic, P1	Z = 2
a = 7.2771 (3) Å	Mo Kα radiation
b = 9.2568 (5) Å	µ = 0.39 mm⁻¹
c = 12.0851 (5) Å	T = 173 K
α = 83.948 (4)°	0.25 × 0.21 × 0.20 mm
β = 84.306 (3)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4303 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	3834 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.926	R_int = 0.013
10307 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	4 restraints
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.40 e Å⁻³
4303 reflections	Δρ_min = −0.28 e Å⁻³
209 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg3^iv	0.95	2.66	3.502 (1)	148

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃ClN₂OS·H₂O
M_r	334.81
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.2771 (3), 9.2568 (5), 12.0851 (5)
α, β, γ (°)	83.948 (4), 84.306 (3), 72.133 (4)
V (Å³)	768.58 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.25 × 0.21 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.908, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	10307, 4303, 3834
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.694

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.089, 1.01
No. of reflections	4303
No. of parameters	209
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.28

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	141.0
C3—H3A···Cg3^iv	0.95	2.66	3.502 (1)	148

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1.

Cg···Cg π-stacking interactions, Cg1, Cg2 and Cg3 are the centroids of rings S1/C6/C1/N1/C7 C1–C6 and C10–C15, respectively. [Symmetry codes: (i) 1-x, -1-y, 1-z; (ii) -x, 2-y, 2-z] top

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)

Acknowledgements

ASP and HSY thank the UoM for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

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