organic compounds
2-Chloro-N-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]acetamide
aDrug Discovery Lab, Department of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, and bPG & Research Department of Physics, Government Arts College, Melur 625 106, India
*Correspondence e-mail: profskabilan@gmail.com
In the title acetamide, C11H8Cl2N2OS, the chlorophenyl ring is oriented at an angle of 7.1 (1)° with respect to the thiazole ring. In the crystal, molecules are linked via C—H⋯O intermolecular interactions, forming C(10) chains propagating in a zigzag manner along the b axis.
CCDC reference: 1483458
Structure description
In a continuation of our work on the . The geometry of the present structure, apart from atom Cl2. is comparable with that reported for a similar structure, namely 2-chloro-N-(4-phenyl-1,3-thiazol-2-yl)acetamide (II) (Saravanan et al., 2016). The superposition of the structures (Fig. 2) using Qmol (Gans & Shalloway, 2001), gives r.m.s. deviations of 0.858 and 0.595 Å, respectively, for molecules A and B in (II). The thiazole ring is planar with a maximum deviation of 0.005 (3) Å for atom C7. Chlorine atom Cl2 is deviates by 0.033 (1) Å from the best plane through the chlorophenyl ring. The chlorophenyl ring is oriented at an angle of 7.1 (1)° to the thiazole ring. The molecular structure is influenced by an intramolecular C—H⋯N short contact (Table 1). In the crystal, C—H⋯O interactions link the molecules, forming C(10) chains propagating along the b axis in a zigzag manner (Fig. 3).
analysis of acetamide derivatives, we have undertaken a single-crystal X-ray diffraction study for the title compound, and the results are presented here. The molecular structure of the title compound is illustrated in Fig. 1Synthesis and crystallization
To a solution of the 4-(4-chlorophenyl) thiazol-2-amine (1.5 g, 7.14 mmol) in dry toluene (25 ml), K2CO3 (1.97 g, 14.28 mmol) and chloroacetyl chloride (0.57 ml, 7.14 mmol) was added. The reaction mixture was heated to reflux for 3 h. After completion of the reaction (monitored by pre-coated TLC), the reaction mixture was cooled to RT and diluted with DCM (45 ml). The organic layer was washed with saturated NaHCO3 solution, water (10 ml × 3) and dried over Na2SO4. The filtrate was concentrated and the crude product mass was purified by precipitation using petroleum ether and diethyl ether (3:1) to give a colorless solid. This solid was recrystallized in ethyl acetate to yield a colorless crystal of the title compound.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1483458
10.1107/S2414314616009032/bt4014sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616009032/bt4014Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616009032/bt4014Isup3.cml
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).C11H8Cl2N2OS | F(000) = 584 |
Mr = 287.15 | Dx = 1.630 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.0940 (12) Å | Cell parameters from 4320 reflections |
b = 14.738 (3) Å | θ = 3.2–26.9° |
c = 15.703 (3) Å | µ = 0.72 mm−1 |
β = 96.932 (9)° | T = 296 K |
V = 1170.3 (4) Å3 | Block, colourless |
Z = 4 | 0.24 × 0.22 × 0.20 mm |
Bruker SMART APEX CCD area-detector diffractometer | Rint = 0.100 |
Radiation source: fine-focus sealed tube | θmax = 27.6°, θmin = 3.1° |
ω scans | h = −6→6 |
6510 measured reflections | k = −18→19 |
2688 independent reflections | l = −20→12 |
1679 reflections with I > 2σ(I) |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.178 | w = 1/[σ2(Fo2) + (0.0772P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
2688 reflections | Δρmax = 0.47 e Å−3 |
160 parameters | Δρmin = −0.41 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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.40270 (17) | 0.34381 (7) | 0.21301 (7) | 0.0471 (3) | |
O1 | 0.3657 (5) | 0.15655 (18) | 0.18809 (18) | 0.0564 (7) | |
N1 | −0.0350 (5) | 0.39261 (18) | 0.12588 (19) | 0.0394 (7) | |
N2 | 0.0005 (6) | 0.2354 (2) | 0.1381 (2) | 0.0438 (7) | |
Cl1 | 0.1848 (3) | −0.02066 (7) | 0.11890 (9) | 0.0789 (5) | |
Cl2 | −0.4015 (2) | 0.82462 (7) | 0.03508 (7) | 0.0614 (4) | |
C1 | −0.2452 (7) | 0.5616 (2) | 0.0659 (2) | 0.0453 (8) | |
H1 | −0.3220 | 0.5072 | 0.0460 | 0.054* | |
C2 | −0.3652 (8) | 0.6429 (3) | 0.0384 (2) | 0.0476 (9) | |
H2A | −0.5208 | 0.6435 | 0.0008 | 0.057* | |
C3 | −0.2477 (7) | 0.7222 (2) | 0.0683 (2) | 0.0418 (8) | |
C4 | −0.0174 (8) | 0.7233 (2) | 0.1237 (2) | 0.0476 (9) | |
H4 | 0.0591 | 0.7780 | 0.1429 | 0.057* | |
C5 | 0.0987 (7) | 0.6419 (2) | 0.1506 (2) | 0.0428 (8) | |
H5 | 0.2545 | 0.6419 | 0.1882 | 0.051* | |
C6 | −0.0146 (6) | 0.5598 (2) | 0.1221 (2) | 0.0358 (7) | |
C7 | 0.1045 (6) | 0.4713 (2) | 0.1506 (2) | 0.0371 (7) | |
C8 | 0.3431 (7) | 0.4571 (2) | 0.1969 (2) | 0.0450 (8) | |
H8 | 0.4594 | 0.5030 | 0.2173 | 0.054* | |
C9 | 0.0985 (6) | 0.3231 (2) | 0.1550 (2) | 0.0376 (8) | |
C10 | 0.1383 (7) | 0.1575 (2) | 0.1540 (2) | 0.0417 (8) | |
C11 | −0.0185 (8) | 0.0745 (2) | 0.1235 (3) | 0.0550 (10) | |
H11A | −0.1120 | 0.0860 | 0.0670 | 0.066* | |
H11B | −0.1490 | 0.0622 | 0.1622 | 0.066* | |
H2 | −0.158 (4) | 0.237 (3) | 0.113 (3) | 0.097 (18)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0321 (5) | 0.0426 (5) | 0.0636 (6) | 0.0025 (4) | −0.0066 (4) | 0.0069 (4) |
O1 | 0.0468 (15) | 0.0449 (15) | 0.0721 (18) | 0.0114 (12) | −0.0144 (13) | −0.0022 (12) |
N1 | 0.0294 (13) | 0.0330 (14) | 0.0553 (18) | 0.0026 (12) | 0.0035 (12) | −0.0003 (12) |
N2 | 0.0324 (15) | 0.0346 (15) | 0.063 (2) | 0.0055 (12) | −0.0021 (14) | −0.0005 (13) |
Cl1 | 0.0867 (9) | 0.0387 (6) | 0.1008 (10) | 0.0226 (6) | −0.0312 (7) | −0.0140 (5) |
Cl2 | 0.0659 (7) | 0.0399 (5) | 0.0780 (8) | 0.0161 (5) | 0.0067 (5) | 0.0094 (4) |
C1 | 0.0434 (19) | 0.0308 (17) | 0.059 (2) | 0.0009 (15) | −0.0051 (16) | −0.0019 (15) |
C2 | 0.046 (2) | 0.045 (2) | 0.050 (2) | 0.0063 (17) | −0.0031 (16) | 0.0050 (16) |
C3 | 0.0453 (19) | 0.0345 (18) | 0.047 (2) | 0.0061 (15) | 0.0113 (16) | 0.0048 (14) |
C4 | 0.051 (2) | 0.0354 (19) | 0.057 (2) | −0.0032 (17) | 0.0087 (17) | −0.0020 (16) |
C5 | 0.0361 (17) | 0.0380 (18) | 0.053 (2) | −0.0023 (15) | −0.0014 (15) | −0.0026 (15) |
C6 | 0.0310 (16) | 0.0369 (17) | 0.0398 (18) | −0.0022 (13) | 0.0057 (13) | 0.0013 (14) |
C7 | 0.0323 (16) | 0.0348 (17) | 0.0439 (19) | −0.0018 (13) | 0.0041 (14) | 0.0007 (13) |
C8 | 0.0373 (18) | 0.040 (2) | 0.055 (2) | −0.0026 (15) | −0.0048 (15) | 0.0018 (15) |
C9 | 0.0258 (15) | 0.0360 (18) | 0.051 (2) | 0.0021 (13) | 0.0047 (14) | 0.0000 (14) |
C10 | 0.0390 (18) | 0.0384 (19) | 0.047 (2) | 0.0102 (15) | 0.0011 (15) | 0.0005 (14) |
C11 | 0.054 (2) | 0.0349 (19) | 0.073 (3) | 0.0117 (17) | −0.0055 (19) | −0.0040 (18) |
S1—C8 | 1.710 (4) | C2—C3 | 1.369 (5) |
S1—C9 | 1.727 (3) | C2—H2A | 0.9300 |
O1—C10 | 1.216 (4) | C3—C4 | 1.374 (5) |
N1—C9 | 1.283 (4) | C4—C5 | 1.381 (5) |
N1—C7 | 1.390 (4) | C4—H4 | 0.9300 |
N2—C10 | 1.352 (4) | C5—C6 | 1.391 (5) |
N2—C9 | 1.401 (4) | C5—H5 | 0.9300 |
N2—H2 | 0.856 (10) | C6—C7 | 1.485 (5) |
Cl1—C11 | 1.750 (4) | C7—C8 | 1.355 (5) |
Cl2—C3 | 1.751 (3) | C8—H8 | 0.9300 |
C1—C6 | 1.382 (5) | C10—C11 | 1.507 (5) |
C1—C2 | 1.390 (5) | C11—H11A | 0.9700 |
C1—H1 | 0.9300 | C11—H11B | 0.9700 |
C8—S1—C9 | 87.85 (16) | C1—C6—C7 | 119.7 (3) |
C9—N1—C7 | 109.6 (3) | C5—C6—C7 | 121.9 (3) |
C10—N2—C9 | 125.7 (3) | C8—C7—N1 | 114.6 (3) |
C10—N2—H2 | 123 (3) | C8—C7—C6 | 127.2 (3) |
C9—N2—H2 | 111 (3) | N1—C7—C6 | 118.1 (3) |
C6—C1—C2 | 121.5 (3) | C7—C8—S1 | 111.2 (3) |
C6—C1—H1 | 119.2 | C7—C8—H8 | 124.4 |
C2—C1—H1 | 119.2 | S1—C8—H8 | 124.4 |
C3—C2—C1 | 118.1 (3) | N1—C9—N2 | 120.5 (3) |
C3—C2—H2A | 120.9 | N1—C9—S1 | 116.8 (3) |
C1—C2—H2A | 120.9 | N2—C9—S1 | 122.7 (2) |
C2—C3—C4 | 122.1 (3) | O1—C10—N2 | 122.5 (3) |
C2—C3—Cl2 | 118.2 (3) | O1—C10—C11 | 124.8 (3) |
C4—C3—Cl2 | 119.7 (3) | N2—C10—C11 | 112.8 (3) |
C3—C4—C5 | 119.0 (3) | C10—C11—Cl1 | 111.7 (3) |
C3—C4—H4 | 120.5 | C10—C11—H11A | 109.3 |
C5—C4—H4 | 120.5 | Cl1—C11—H11A | 109.3 |
C4—C5—C6 | 120.7 (3) | C10—C11—H11B | 109.3 |
C4—C5—H5 | 119.6 | Cl1—C11—H11B | 109.3 |
C6—C5—H5 | 119.6 | H11A—C11—H11B | 107.9 |
C1—C6—C5 | 118.4 (3) | ||
C6—C1—C2—C3 | 0.3 (6) | C5—C6—C7—N1 | 173.7 (3) |
C1—C2—C3—C4 | 0.2 (6) | N1—C7—C8—S1 | −0.8 (4) |
C1—C2—C3—Cl2 | −179.0 (3) | C6—C7—C8—S1 | −178.5 (3) |
C2—C3—C4—C5 | −0.4 (6) | C9—S1—C8—C7 | 0.3 (3) |
Cl2—C3—C4—C5 | 178.8 (3) | C7—N1—C9—N2 | −179.5 (3) |
C3—C4—C5—C6 | 0.1 (5) | C7—N1—C9—S1 | −0.9 (4) |
C2—C1—C6—C5 | −0.5 (5) | C10—N2—C9—N1 | 169.4 (3) |
C2—C1—C6—C7 | 179.1 (3) | C10—N2—C9—S1 | −9.1 (5) |
C4—C5—C6—C1 | 0.3 (5) | C8—S1—C9—N1 | 0.4 (3) |
C4—C5—C6—C7 | −179.3 (3) | C8—S1—C9—N2 | 178.9 (3) |
C9—N1—C7—C8 | 1.1 (4) | C9—N2—C10—O1 | 2.4 (6) |
C9—N1—C7—C6 | 179.0 (3) | C9—N2—C10—C11 | −176.6 (3) |
C1—C6—C7—C8 | 171.7 (4) | O1—C10—C11—Cl1 | −14.5 (5) |
C5—C6—C7—C8 | −8.6 (6) | N2—C10—C11—Cl1 | 164.5 (3) |
C1—C6—C7—N1 | −6.0 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···N1 | 0.93 | 2.47 | 2.827 (4) | 103 |
C5—H5···O1i | 0.93 | 2.58 | 3.498 (5) | 169 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
Footnotes
‡Additional correspondence author, e-mail: s_selvanayagam@rediffmail.com.
Acknowledgements
The authors are thankful for the funding support from the Department of Biotechnology North East Collaboration (DBT NEC) Research Project, Grant No. BT/252/NE/TBP/2011, New Delhi, India.
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