2-Chloro-N-(4-phenyl-1,3-thia­zol-2-yl)acetamide

Saravanan, K.; Elancheran, R.; Divakar, S.; Kabilan, S.; Selvanayagam, S.

doi:10.1107/S2414314616008798

organic compounds

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ISSN: 2414-3146

Volume 1| Part 6| June 2016| x160879

doi:10.1107/S2414314616008798

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2-Chloro-N-(4-phenyl-1,3-thiazol-2-yl)acetamide

K. Saravanan,^a R. Elancheran,^b S. Divakar,^c S. Kabilan ^a ^* and S. Selvanayagam ^d ‡

^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

Edited by O. Blacque, University of Zürich, Switzerland (Received 24 May 2016; accepted 30 May 2016; online 3 June 2016)

The title acetamide, C₁₁H₉ClN₂OS, crystallizes with two independent molecules in the asymmetric unit 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 asymmetric unit 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).

Table 1
Hydrogen-bond geometry (Å, °)

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.

Figure 1
The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
Superposition of molecule A (red) with the molecule B (purple).

In the crystal, C—H⋯N hydrogen bonds link the molecules, forming C(10) chains propagating along [ $[\overline{1}]$ 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.

Figure 3
Crystal packing of the title compound, viewed along the a axis. The C—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1

). For clarity, H atoms not involved in these hydrogen bonds have been omitted.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₁H₉ClN₂OS
M_r	252.71
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	8.0406 (9), 9.2313 (14), 15.9898 (17)
α, β, γ (°)	85.693 (19), 76.448 (19), 87.082 (19)
V (Å³)	1149.9 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.49
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
No. of measured, independent and observed [I > 2σ(I)] reflections	6721, 5129, 3519
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.174, 1.03
No. of reflections	5129
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.52
Computer programs: SMART and SAINT (Bruker, 2002 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1482671

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616008798/zq4007sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616008798/zq4007Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616008798/zq4007Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: 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).

2-Chloro-N-(4-phenyl-1,3-thiazol-2-yl)acetamide top

Crystal data top

C₁₁H₉ClN₂OS	Z = 4
M_r = 252.71	F(000) = 520
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	R_int = 0.045
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 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 top

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(F_o²) + (0.0971P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5129 reflections	Δρ_max = 0.44 e Å⁻³
289 parameters	Δρ_min = −0.52 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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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