organic compounds
2-Chloro-N-(4-phenyl-1,3-thiazol-2-yl)acetamide
aDrug Discovery Lab, Department of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, bDrug Discovery Laboratory, Life Sciences Division, Institute of Advanced Study in Science and Technology, Guwahati, Assam 781 035, India, cDepartment of Pharmacology, PSG College of Pharmacy, Coimbatore 641 004, India, and dPG & Research Department of Physics, Government Arts College, Melur 625 106, India
*Correspondence e-mail: profskabilan@gmail.com
The title acetamide, C11H9ClN2OS, crystallizes with two independent molecules in the whose geometrical features are similar. The phenyl ring is oriented at angles of 2.5 (1) and 6.2 (1)° with respect to the thiazole ring in the two molecules. In the crystal, molecules are linked via C—H⋯N hydrogen bonds which form C(10) chains along the [-100] direction. The chains are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming C(8) chains along the [100] direction.
Keywords: crystal structure; acetamide derivatives; N—H⋯O; C—H⋯N; C—H⋯O; hydrogen bonds.
CCDC reference: 1482671
Structure description
Acetamide derivatives are new potential PET tracers for imaging nucleotide pyrophosphatase/phosphodiesterase (Gao et al., 2016). These derivatives act as anticholinesterase agents for a possible role in the management of Alzheimer's disease (Sun et al., 2016). Acetamide derivatives possess anticonvulsant, antidepressant (Zhen et al., 2015) and anti-HIV (Huang et al., 2016) activities. In view of the many interesting applications of acetamide derivatives we synthesized the title compound and report herein its crystal structure.
The X-ray study confirmed the molecular structure and atomic connectivity, as illustrated in Fig. 1. The contains two molecules (Fig. 1); their corresponding bond lengths and bond angles are in good agreement. Fig. 2 shows a superposition of the thiazole ring of both the molecules using Qmol (Gans & Shalloway, 2001); the r.m.s. deviation is 0.734 Å. The phenyl ring and thiazole rings are coplanar with the maximum deviation of 0.007 (3) and 0.003 (3) Å for atom C9 in molecules A and B, respectively. The phenyl ring is oriented at angles of 2.5 (1) and 6.2 (1)°, respectively, to the thiazole ring in molecules A and B. The molecular structure is influenced by four intramolecular hydrogen bonds of N—H⋯O, C—H⋯N and C—H⋯O types (Table 1).
In the crystal, C—H⋯N hydrogen bonds link the molecules, forming C(10) chains propagating along [00]. In addition to this, N—H⋯O and C—H⋯O hydrogen bonds also link the molecules into C(8) chains propagating along [100]; see Fig. 3.
Synthesis and crystallization
To a solution of 4-phenylthiazol-2-amine (1.5 g, 8.52 mmol) in dry toluene (25 ml), K2CO3 (2.32 g, 17.04 mmol) and chloroacetyl chloride (0.67 ml, 8.52 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 colorless crystals of the title compound.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 1482671
10.1107/S2414314616008798/zq4007sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616008798/zq4007Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616008798/zq4007Isup3.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).C11H9ClN2OS | Z = 4 |
Mr = 252.71 | F(000) = 520 |
Triclinic, P1 | Dx = 1.460 Mg m−3 |
a = 8.0406 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.2313 (14) Å | Cell parameters from 4218 reflections |
c = 15.9898 (17) Å | θ = 3.2–26.8° |
α = 85.693 (19)° | µ = 0.49 mm−1 |
β = 76.448 (19)° | T = 296 K |
γ = 87.082 (19)° | Block, colourless |
V = 1149.9 (3) Å3 | 0.22 × 0.20 × 0.18 mm |
Bruker SMART APEX CCD area-detector diffractometer | Rint = 0.045 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −10→10 |
6721 measured reflections | k = −11→7 |
5129 independent reflections | l = −20→19 |
3519 reflections with I > 2σ(I) |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.174 | w = 1/[σ2(Fo2) + (0.0971P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5129 reflections | Δρmax = 0.44 e Å−3 |
289 parameters | Δρmin = −0.52 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 | 0.41465 (9) | 0.74959 (7) | 0.15473 (5) | 0.0538 (2) | |
O1 | 0.6150 (3) | 0.66650 (18) | 0.27078 (12) | 0.0597 (5) | |
N1 | 0.4150 (3) | 1.0270 (2) | 0.15895 (13) | 0.0471 (5) | |
N2 | 0.5584 (3) | 0.9072 (2) | 0.25671 (14) | 0.0519 (5) | |
H2 | 0.5680 | 0.9893 | 0.2769 | 0.062* | |
Cl1 | 0.94512 (12) | 0.88155 (11) | 0.28862 (7) | 0.0922 (3) | |
C1 | 0.2855 (4) | 1.2645 (3) | 0.06344 (19) | 0.0622 (7) | |
H1 | 0.3388 | 1.2834 | 0.1070 | 0.075* | |
C2 | 0.2265 (5) | 1.3788 (4) | 0.0159 (2) | 0.0750 (9) | |
H2A | 0.2410 | 1.4739 | 0.0277 | 0.090* | |
C3 | 0.1468 (4) | 1.3534 (4) | −0.0483 (2) | 0.0714 (9) | |
H3 | 0.1069 | 1.4307 | −0.0799 | 0.086* | |
C4 | 0.1266 (4) | 1.2125 (4) | −0.0654 (2) | 0.0695 (8) | |
H4 | 0.0721 | 1.1944 | −0.1087 | 0.083* | |
C5 | 0.1860 (3) | 1.0988 (3) | −0.01938 (18) | 0.0599 (7) | |
H5 | 0.1726 | 1.0043 | −0.0325 | 0.072* | |
C6 | 0.2660 (3) | 1.1213 (3) | 0.04659 (16) | 0.0493 (6) | |
C7 | 0.3300 (3) | 0.9994 (3) | 0.09627 (16) | 0.0467 (5) | |
C8 | 0.3176 (3) | 0.8557 (3) | 0.08623 (18) | 0.0554 (6) | |
H8 | 0.2633 | 0.8197 | 0.0472 | 0.066* | |
C9 | 0.4664 (3) | 0.9065 (2) | 0.19303 (16) | 0.0460 (5) | |
C10 | 0.6333 (4) | 0.7901 (3) | 0.28888 (16) | 0.0518 (6) | |
C11 | 0.7436 (5) | 0.8203 (3) | 0.3497 (2) | 0.0696 (8) | |
H11A | 0.7600 | 0.7325 | 0.3845 | 0.084* | |
H11B | 0.6877 | 0.8940 | 0.3879 | 0.084* | |
S1' | 0.69249 (11) | 1.20434 (7) | 0.49270 (4) | 0.0608 (2) | |
O1' | 0.6147 (3) | 1.15393 (19) | 0.33948 (13) | 0.0642 (5) | |
N1' | 0.7240 (3) | 1.4819 (2) | 0.47406 (13) | 0.0466 (5) | |
N2' | 0.6465 (3) | 1.3901 (2) | 0.35679 (13) | 0.0468 (5) | |
H2' | 0.6406 | 1.4773 | 0.3344 | 0.056* | |
Cl1' | 0.76597 (12) | 1.26828 (10) | 0.14499 (5) | 0.0814 (3) | |
C1' | 0.8038 (4) | 1.6899 (3) | 0.58315 (19) | 0.0668 (8) | |
H1' | 0.7653 | 1.7229 | 0.5344 | 0.080* | |
C2' | 0.8529 (5) | 1.7902 (4) | 0.6332 (2) | 0.0803 (10) | |
H2'1 | 0.8495 | 1.8890 | 0.6168 | 0.096* | |
C3' | 0.9056 (4) | 1.7439 (4) | 0.7057 (2) | 0.0743 (9) | |
H3' | 0.9367 | 1.8108 | 0.7395 | 0.089* | |
C4' | 0.9128 (4) | 1.6001 (4) | 0.7287 (2) | 0.0722 (9) | |
H4' | 0.9494 | 1.5688 | 0.7783 | 0.087* | |
C5' | 0.8667 (4) | 1.4990 (4) | 0.67955 (18) | 0.0635 (7) | |
H5' | 0.8725 | 1.4006 | 0.6964 | 0.076* | |
C6' | 0.8115 (3) | 1.5434 (3) | 0.60490 (15) | 0.0499 (6) | |
C8' | 0.7508 (4) | 1.2908 (3) | 0.57165 (17) | 0.0616 (7) | |
H8' | 0.7719 | 1.2440 | 0.6219 | 0.074* | |
C7' | 0.7626 (3) | 1.4359 (3) | 0.55226 (16) | 0.0484 (6) | |
C9' | 0.6865 (3) | 1.3722 (2) | 0.43644 (15) | 0.0442 (5) | |
C10' | 0.6162 (3) | 1.2810 (3) | 0.31178 (17) | 0.0493 (6) | |
C11' | 0.5852 (4) | 1.3246 (3) | 0.22428 (18) | 0.0606 (7) | |
H11C | 0.5675 | 1.4292 | 0.2180 | 0.073* | |
H11D | 0.4836 | 1.2792 | 0.2172 | 0.073* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0635 (4) | 0.0347 (3) | 0.0662 (4) | −0.0070 (3) | −0.0186 (3) | −0.0062 (3) |
O1 | 0.0932 (14) | 0.0277 (9) | 0.0627 (11) | −0.0032 (8) | −0.0277 (10) | −0.0004 (7) |
N1 | 0.0563 (12) | 0.0366 (11) | 0.0501 (11) | 0.0005 (8) | −0.0161 (10) | −0.0035 (8) |
N2 | 0.0778 (14) | 0.0266 (10) | 0.0575 (12) | −0.0018 (9) | −0.0284 (11) | −0.0016 (8) |
Cl1 | 0.0911 (6) | 0.0810 (6) | 0.1208 (8) | −0.0078 (5) | −0.0587 (6) | 0.0006 (5) |
C1 | 0.0819 (19) | 0.0519 (16) | 0.0561 (15) | 0.0180 (14) | −0.0240 (15) | −0.0127 (12) |
C2 | 0.100 (2) | 0.0563 (18) | 0.0677 (18) | 0.0238 (16) | −0.0231 (18) | −0.0052 (14) |
C3 | 0.0649 (18) | 0.082 (2) | 0.0639 (18) | 0.0227 (16) | −0.0162 (15) | 0.0076 (16) |
C4 | 0.0519 (16) | 0.096 (3) | 0.0615 (17) | −0.0006 (15) | −0.0196 (14) | 0.0078 (16) |
C5 | 0.0510 (14) | 0.0690 (18) | 0.0610 (16) | −0.0056 (12) | −0.0153 (13) | −0.0022 (13) |
C6 | 0.0421 (12) | 0.0552 (15) | 0.0483 (13) | 0.0050 (10) | −0.0075 (11) | −0.0026 (11) |
C7 | 0.0437 (12) | 0.0469 (14) | 0.0483 (13) | 0.0017 (10) | −0.0079 (11) | −0.0059 (10) |
C8 | 0.0569 (15) | 0.0481 (15) | 0.0657 (16) | −0.0042 (11) | −0.0208 (13) | −0.0100 (12) |
C9 | 0.0536 (13) | 0.0337 (12) | 0.0492 (12) | −0.0032 (10) | −0.0092 (11) | −0.0015 (10) |
C10 | 0.0728 (16) | 0.0315 (12) | 0.0519 (14) | −0.0019 (11) | −0.0179 (13) | 0.0020 (10) |
C11 | 0.111 (2) | 0.0408 (15) | 0.0692 (18) | −0.0006 (15) | −0.0469 (18) | 0.0018 (13) |
S1' | 0.0902 (5) | 0.0375 (4) | 0.0573 (4) | −0.0053 (3) | −0.0232 (4) | 0.0022 (3) |
O1' | 0.1028 (15) | 0.0296 (9) | 0.0690 (12) | −0.0025 (9) | −0.0376 (11) | −0.0031 (8) |
N1' | 0.0553 (12) | 0.0376 (10) | 0.0483 (11) | −0.0034 (8) | −0.0133 (9) | −0.0060 (8) |
N2' | 0.0636 (12) | 0.0273 (9) | 0.0530 (11) | −0.0020 (8) | −0.0204 (10) | −0.0024 (8) |
Cl1' | 0.0989 (6) | 0.0854 (6) | 0.0611 (5) | −0.0138 (5) | −0.0171 (4) | −0.0099 (4) |
C1' | 0.090 (2) | 0.0596 (18) | 0.0573 (16) | −0.0143 (15) | −0.0277 (16) | −0.0062 (13) |
C2' | 0.115 (3) | 0.062 (2) | 0.070 (2) | −0.0206 (18) | −0.028 (2) | −0.0120 (16) |
C3' | 0.078 (2) | 0.086 (2) | 0.0618 (18) | −0.0208 (17) | −0.0133 (16) | −0.0223 (17) |
C4' | 0.074 (2) | 0.092 (3) | 0.0545 (16) | −0.0065 (17) | −0.0194 (15) | −0.0140 (16) |
C5' | 0.0713 (18) | 0.0669 (19) | 0.0530 (15) | −0.0022 (14) | −0.0145 (14) | −0.0088 (13) |
C6' | 0.0498 (13) | 0.0573 (15) | 0.0399 (12) | −0.0065 (11) | −0.0022 (11) | −0.0089 (10) |
C8' | 0.0834 (19) | 0.0532 (17) | 0.0498 (14) | −0.0042 (13) | −0.0200 (14) | 0.0033 (12) |
C7' | 0.0498 (13) | 0.0512 (14) | 0.0428 (12) | −0.0022 (10) | −0.0074 (11) | −0.0044 (10) |
C9' | 0.0510 (13) | 0.0352 (12) | 0.0458 (12) | 0.0007 (9) | −0.0103 (11) | −0.0032 (9) |
C10' | 0.0606 (15) | 0.0331 (13) | 0.0576 (14) | 0.0004 (10) | −0.0203 (12) | −0.0046 (10) |
C11' | 0.085 (2) | 0.0399 (14) | 0.0648 (16) | −0.0004 (12) | −0.0335 (15) | −0.0056 (12) |
S1—C8 | 1.712 (3) | S1'—C8' | 1.708 (3) |
S1—C9 | 1.720 (2) | S1'—C9' | 1.737 (2) |
O1—C10 | 1.222 (3) | O1'—C10' | 1.222 (3) |
N1—C9 | 1.294 (3) | N1'—C9' | 1.298 (3) |
N1—C7 | 1.383 (3) | N1'—C7' | 1.389 (3) |
N2—C10 | 1.338 (3) | N2'—C10' | 1.344 (3) |
N2—C9 | 1.393 (3) | N2'—C9' | 1.381 (3) |
N2—H2 | 0.8600 | N2'—H2' | 0.8600 |
Cl1—C11 | 1.780 (4) | Cl1'—C11' | 1.774 (3) |
C1—C2 | 1.384 (4) | C1'—C6' | 1.373 (4) |
C1—C6 | 1.392 (4) | C1'—C2' | 1.397 (4) |
C1—H1 | 0.9300 | C1'—H1' | 0.9300 |
C2—C3 | 1.370 (5) | C2'—C3' | 1.358 (5) |
C2—H2A | 0.9300 | C2'—H2'1 | 0.9300 |
C3—C4 | 1.375 (5) | C3'—C4' | 1.352 (5) |
C3—H3 | 0.9300 | C3'—H3' | 0.9300 |
C4—C5 | 1.367 (4) | C4'—C5' | 1.381 (4) |
C4—H4 | 0.9300 | C4'—H4' | 0.9300 |
C5—C6 | 1.391 (4) | C5'—C6' | 1.395 (4) |
C5—H5 | 0.9300 | C5'—H5' | 0.9300 |
C6—C7 | 1.470 (3) | C6'—C7' | 1.473 (4) |
C7—C8 | 1.359 (4) | C8'—C7' | 1.354 (4) |
C8—H8 | 0.9300 | C8'—H8' | 0.9300 |
C10—C11 | 1.510 (4) | C10'—C11' | 1.500 (4) |
C11—H11A | 0.9700 | C11'—H11C | 0.9700 |
C11—H11B | 0.9700 | C11'—H11D | 0.9700 |
C8—S1—C9 | 88.17 (12) | C8'—S1'—C9' | 88.18 (13) |
C9—N1—C7 | 110.4 (2) | C9'—N1'—C7' | 110.5 (2) |
C10—N2—C9 | 125.1 (2) | C10'—N2'—C9' | 124.7 (2) |
C10—N2—H2 | 117.4 | C10'—N2'—H2' | 117.6 |
C9—N2—H2 | 117.4 | C9'—N2'—H2' | 117.6 |
C2—C1—C6 | 120.6 (3) | C6'—C1'—C2' | 121.0 (3) |
C2—C1—H1 | 119.7 | C6'—C1'—H1' | 119.5 |
C6—C1—H1 | 119.7 | C2'—C1'—H1' | 119.5 |
C3—C2—C1 | 120.7 (3) | C3'—C2'—C1' | 120.1 (3) |
C3—C2—H2A | 119.7 | C3'—C2'—H2'1 | 119.9 |
C1—C2—H2A | 119.7 | C1'—C2'—H2'1 | 119.9 |
C2—C3—C4 | 119.3 (3) | C4'—C3'—C2' | 119.8 (3) |
C2—C3—H3 | 120.4 | C4'—C3'—H3' | 120.1 |
C4—C3—H3 | 120.4 | C2'—C3'—H3' | 120.1 |
C5—C4—C3 | 120.5 (3) | C3'—C4'—C5' | 120.9 (3) |
C5—C4—H4 | 119.8 | C3'—C4'—H4' | 119.5 |
C3—C4—H4 | 119.8 | C5'—C4'—H4' | 119.5 |
C4—C5—C6 | 121.5 (3) | C4'—C5'—C6' | 120.5 (3) |
C4—C5—H5 | 119.2 | C4'—C5'—H5' | 119.7 |
C6—C5—H5 | 119.2 | C6'—C5'—H5' | 119.7 |
C5—C6—C1 | 117.5 (3) | C1'—C6'—C5' | 117.6 (3) |
C5—C6—C7 | 121.7 (3) | C1'—C6'—C7' | 121.8 (2) |
C1—C6—C7 | 120.8 (2) | C5'—C6'—C7' | 120.6 (3) |
C8—C7—N1 | 114.1 (2) | C7'—C8'—S1' | 111.8 (2) |
C8—C7—C6 | 126.2 (2) | C7'—C8'—H8' | 124.1 |
N1—C7—C6 | 119.7 (2) | S1'—C8'—H8' | 124.1 |
C7—C8—S1 | 111.3 (2) | C8'—C7'—N1' | 114.1 (2) |
C7—C8—H8 | 124.3 | C8'—C7'—C6' | 126.6 (2) |
S1—C8—H8 | 124.3 | N1'—C7'—C6' | 119.3 (2) |
N1—C9—N2 | 120.7 (2) | N1'—C9'—N2' | 121.4 (2) |
N1—C9—S1 | 116.1 (2) | N1'—C9'—S1' | 115.38 (19) |
N2—C9—S1 | 123.19 (18) | N2'—C9'—S1' | 123.22 (18) |
O1—C10—N2 | 123.0 (3) | O1'—C10'—N2' | 122.7 (2) |
O1—C10—C11 | 121.6 (2) | O1'—C10'—C11' | 121.6 (2) |
N2—C10—C11 | 115.4 (2) | N2'—C10'—C11' | 115.7 (2) |
C10—C11—Cl1 | 109.2 (2) | C10'—C11'—Cl1' | 108.7 (2) |
C10—C11—H11A | 109.8 | C10'—C11'—H11C | 110.0 |
Cl1—C11—H11A | 109.8 | Cl1'—C11'—H11C | 110.0 |
C10—C11—H11B | 109.8 | C10'—C11'—H11D | 110.0 |
Cl1—C11—H11B | 109.8 | Cl1'—C11'—H11D | 110.0 |
H11A—C11—H11B | 108.3 | H11C—C11'—H11D | 108.3 |
C6—C1—C2—C3 | 0.4 (5) | C6'—C1'—C2'—C3' | −1.5 (5) |
C1—C2—C3—C4 | −0.3 (5) | C1'—C2'—C3'—C4' | 1.0 (5) |
C2—C3—C4—C5 | −0.4 (5) | C2'—C3'—C4'—C5' | −0.2 (5) |
C3—C4—C5—C6 | 0.9 (4) | C3'—C4'—C5'—C6' | 0.0 (5) |
C4—C5—C6—C1 | −0.8 (4) | C2'—C1'—C6'—C5' | 1.3 (5) |
C4—C5—C6—C7 | 180.0 (2) | C2'—C1'—C6'—C7' | −179.1 (3) |
C2—C1—C6—C5 | 0.2 (4) | C4'—C5'—C6'—C1' | −0.5 (4) |
C2—C1—C6—C7 | 179.4 (3) | C4'—C5'—C6'—C7' | 179.9 (3) |
C9—N1—C7—C8 | 1.1 (3) | C9'—S1'—C8'—C7' | −0.1 (2) |
C9—N1—C7—C6 | −177.7 (2) | S1'—C8'—C7'—N1' | 0.5 (3) |
C5—C6—C7—C8 | −1.3 (4) | S1'—C8'—C7'—C6' | −179.2 (2) |
C1—C6—C7—C8 | 179.5 (3) | C9'—N1'—C7'—C8' | −0.7 (3) |
C5—C6—C7—N1 | 177.4 (2) | C9'—N1'—C7'—C6' | 179.0 (2) |
C1—C6—C7—N1 | −1.8 (4) | C1'—C6'—C7'—C8' | −173.7 (3) |
N1—C7—C8—S1 | −0.6 (3) | C5'—C6'—C7'—C8' | 5.9 (4) |
C6—C7—C8—S1 | 178.07 (19) | C1'—C6'—C7'—N1' | 6.6 (4) |
C9—S1—C8—C7 | 0.0 (2) | C5'—C6'—C7'—N1' | −173.8 (2) |
C7—N1—C9—N2 | 178.7 (2) | C7'—N1'—C9'—N2' | −178.8 (2) |
C7—N1—C9—S1 | −1.1 (3) | C7'—N1'—C9'—S1' | 0.7 (3) |
C10—N2—C9—N1 | −172.1 (2) | C10'—N2'—C9'—N1' | 176.0 (2) |
C10—N2—C9—S1 | 7.7 (4) | C10'—N2'—C9'—S1' | −3.5 (4) |
C8—S1—C9—N1 | 0.7 (2) | C8'—S1'—C9'—N1' | −0.3 (2) |
C8—S1—C9—N2 | −179.2 (2) | C8'—S1'—C9'—N2' | 179.1 (2) |
C9—N2—C10—O1 | −6.9 (4) | C9'—N2'—C10'—O1' | 3.0 (4) |
C9—N2—C10—C11 | 173.0 (2) | C9'—N2'—C10'—C11' | −176.5 (2) |
O1—C10—C11—Cl1 | 100.9 (3) | O1'—C10'—C11'—Cl1' | −71.5 (3) |
N2—C10—C11—Cl1 | −79.0 (3) | N2'—C10'—C11'—Cl1' | 108.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···N1′i | 0.97 | 2.62 | 3.565 (4) | 165 |
N2′—H2′···O1ii | 0.86 | 1.98 | 2.835 (3) | 172 |
C11′—H11C···O1ii | 0.97 | 2.48 | 3.329 (3) | 146 |
N2—H2···O1′ | 0.86 | 1.98 | 2.825 (3) | 168 |
C1—H1···N1 | 0.93 | 2.54 | 2.869 (4) | 101 |
C1′—H1′···N1′ | 0.93 | 2.56 | 2.880 (4) | 101 |
C11—H11B···O1′ | 0.97 | 2.55 | 3.204 (3) | 125 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
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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