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N-(4-Chloro-1,3-benzothiazol-2-yl)-2-(3-methylphenyl)acetamide monohydrate
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
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
|
Refinement
|
|
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell 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.
Supporting information
https://doi.org/10.1107/S1600536811035872/im2316sup1.cif
contains datablocks global, I. DOI: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
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).
H20A, H20B and H2N were located by a Fourier map and refined isotropically. All other H atoms were placed in their calculated positions and then refined using the riding model with atom—H lengths of 0.95Å (CH), 0.99Å (CH2) or 0.98Å (CH3). Isotropic displacement parameters for these atoms were set to 1.18-1.21 (CH) 1.20 CH2) or 1.51 (CH3) times Ueq of the parent atom.
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).
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 the title compound is synthesized and its 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).
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).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
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).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 monochromator | 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 |
C16H13ClN2OS·H2O | γ = 72.133 (4)° |
Mr = 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)° |
Oxford Diffraction Xcalibur Eos Gemini diffractometer | 4303 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | 3834 reflections with I > 2σ(I) |
Tmin = 0.908, Tmax = 0.926 | Rint = 0.013 |
10307 measured reflections |
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 | Δρmax = 0.40 e Å−3 |
4303 reflections | Δρmin = −0.28 e Å−3 |
209 parameters |
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 |
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 |
Mr | 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) |
Tmin, Tmax | 0.908, 0.926 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10307, 4303, 3834 |
Rint | 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 |
Δρmax, Δρmin (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).
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···Cg3iv | 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. |
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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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).