The crystal structure of 6-(4-chloro­phen­yl)-2-(4-methyl­benz­yl)imidazo[2,1-b][1,3,4]thia­diazole-5-carbaldehyde

Sowmya, A.; Anil Kumar, G.N.; Kumar, S.; Karki, S.S.

doi:10.1107/S2056989016014754

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Volume 72| Part 10| October 2016| Pages 1460-1462

https://doi.org/10.1107/S2056989016014754

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The crystal structure of 6-(4-chlorophenyl)-2-(4-methylbenzyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde

A. Sowmya,^a G. N. Anil Kumar,^a ^* Sujeet Kumar ^b and Subhas S. Karki ^b

^aDepartment of Physics, M. S. Ramaiah Institute of Technology, Bangalore, India, and ^bDepartment of Pharmaceutical Chemistry, KLE University's College of Pharmacy, Bangalore 560 010, India
^*Correspondence e-mail: anilgn@msrit.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 September 2016; accepted 18 September 2016; online 23 September 2016)

In the title imidazo[2,1-b][1,3,4]thiadiazole derivative, C₁₉H₁₄ClN₃OS, the 4-methylbenzyl and chlorophenyl rings are inclined to the planar imidazo[2,1-b][1,3,4]thiadiazole moiety (r.m.s. deviation = 0.012 Å) by 64.5 (1) and 3.7 (1)°, respectively. The molecular structure is primarily stabilized by a strong intramolecular C—H⋯O hydrogen bond, leading to the formation of a pseudo-seven-membered S(7) ring motif, and a short intramolecular C—H⋯N contact forming an S(5) ring motif. In the crystal, molecules are linked by pairs of C—H⋯S hydrogen bonds, forming inversion dimers. The dimers are linked by C—H⋯O and C—H⋯π interactions, forming chains propagating along [110].

Keywords: crystal structure; imidazo[2,1-b][1,3,4]thiadiazole; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 1504989

1. Chemical context

The search for potential drugs to fight cancer and the design of molecules with limited side effects, particularly to the immune system, is an emerging area of research. Imidazo[2,1-b][1,3,4]thiadiazole derivatives have been reported for their promising biological activities, and the most recent studies indicate their potential as antitumor agents (Karki et al., 2011 ). However, active heterocyclic pharmacophores particularly at position 5 of the imidazo[2,1-b][1,3,4]thiadiazole moiety have shown significant activities; substitution of aldehydes at the 5-position resulted in an improvement of their anticancer activity (Kumar et al., 2014 ), whereas a substituted phenyl group enhanced the anti-tubercular activity (Ramprasad et al., 2015 ). In view of the above, we report herein on the synthesis and crystal structure of title imidazo[2,1-b][1,3,4]thiadiazole derivative.

2. Structural commentary

The molecular structure of the title compound is illustrated in Fig. 1. The carbaldehyde group is coplanar with the imidazothiadiazole ring system and cis to the chlorophenyl ring. Bond C12=O1 is cis to the C13—C14 bond, which favours the formation of an intramolecular C15—H15⋯O1 hydrogen bond (Table 1). The imidazole and thiadiazole rings show different π conjugations, resulting from their fused nature and also due to the groups attached to them. This is evident from the differences in the bond lengths S1—C9 [1.772 (4) Å] and S1—C10 [1.724 (2) Å] of the thiadiazole ring, indicating that the resonance effect caused by the imidazole ring is stronger than that caused by the thiadiazole ring. As a result, the imidazole system is more resonance stabilized. Additionally, the imidazothiadiazole moiety is planar and rigid with maximum deviations of 0.0182 (2) and −0.0078 (3) Å for atoms N2 and C13, respectively, from the mean plane. The 4-chlorophenyl ring makes a dihedral angle of 3.7 (1)°, whereas the 4-methylbenzyl ring is inclined at an angle of 64.5 (1)° with respect to the mean plane of the imidazothiadiazole ring system. The molecular structure is primarily stabilized by the strong intramolecular C15—H15⋯O1 hydrogen bond, leading to the formation of a pseudo-seven-membered hydrogen-bonded S(7) ring motif, and an intramolecular C19—H19⋯N3 interaction forming an S(5) ring motif, thus locking the molecular conformation and eliminating conformational flexibility (Fig. 1 and Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1	0.93	2.20	3.047 (3)	151
C19—H19⋯N3	0.93	2.42	2.788 (3)	103
C19—H19⋯S1ⁱ	0.93	2.83	3.733 (2)	165
C6—H6⋯O1ⁱⁱ	0.93	2.46	3.384 (3)	170
C18—H18⋯Cgⁱ	0.93	2.92	3.648 (12)	136
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+2, -z.

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at 50% probability level. The intramolecular interactions are shown as dashed lines (see Table 1

3. Supramolecular features

In the crystal, the solid-state structure is stabilized primarily by a pair of C—H⋯S hydrogen bonds, forming inversion dimers (Table 1 and Fig. 2). These dimers are linked by pairs of C—H⋯O hydrogen bonds and C—H⋯π interactions, forming chains propagating along [110]. There are no halogen interactions involving the chlorine atom, and no aromatic π–π stacking interactions present.

Figure 2
A view along the a axis of the crystal packing of the title compound. The intermolecular interactions are shown as dashed lines (see Table 1

) and, for clarity, H atoms not involved in these interactions have been omitted.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.37, last update May 2016; Groom et al., 2016 ) gave 55 hits for molecules containing the imidazo[2,1-b][1,3,4]thiadiazole moiety. A search for 2-benzyl-6-phenylimidazo[2,1-b][1,3,4]thiadiazoles gave ten hits, and five of these compounds contain a 6-phenylimidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde moiety. It is interesting to note that the aldehyde group generally accepts a hydrogen bond, and that the para-substituted halogens do not generate any significant weak interactions in the crystal packing, except for a C—H⋯F interaction in 2-(4-fluorobenzyl)-6-phenylimidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde (OWIFAC; Banu et al., 2010 ), the 4-fluorobenzyl analogue of the title compound.

5. Synthesis and crystallization

The title compound was obtained according to a reported procedure (Kumar et al., 2014). The Vilsmeier reagent was prepared at 273–278 K by adding dropwise phosphorous oxychloride (2.3 g, 15 mmol) into a stirred solution of DMF (10 ml). The 6-(4-chlorophenyl)-2-(4-methylbenzyl) imidazo[2,1-b][1,3,4]thiadiazole (4 mmol) was added slowly to the Vilsmeier reagent with stirring and cooling for 2 h. Further stirring was continued for 6 h at 353–363 K. The reaction mixture was then poured into 100 ml of water. The precipitate obtained was filtered, and neutralized with a cold aqueous solution of sodium carbonate. The solid obtained was filtered, washed with water and dried. Single crystals were obtained by slow evaporation of a solution in ethanol/DMF (2:1 v:v).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically, with N—H = 0.86 Å and C—H = 0.93–0.96 Å, and constrained to ride on their parent atoms with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C,N) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₄ClN₃OS
M_r	367.84
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	5.6138 (18), 9.018 (2), 16.514 (5)
α, β, γ (°)	80.533 (13), 87.519 (14), 83.353 (14)
V (Å³)	818.9 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.37
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2012 )
T_min, T_max	0.941, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	12059, 2966, 2530
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.110, 1.05
No. of reflections	2966
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.26
Computer programs: SMART and SAINT (Bruker, 2012), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), CAMERON (Watkin et al., 1996 ), Mercury (Macrae et al., 2008 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1504989

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989016014754/su5325sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016014754/su5325Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016014754/su5325Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); 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), CAMERON (Watkin et al., 1996) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

6-(4-Chlorophenyl)-2-(4-methylbenzyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde top

Crystal data top

C₁₉H₁₄ClN₃OS	Z = 2
M_r = 367.84	F(000) = 380
Triclinic, P1	D_x = 1.492 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6138 (18) Å	Cell parameters from 1890 reflections
b = 9.018 (2) Å	θ = 3.3–26.4°
c = 16.514 (5) Å	µ = 0.37 mm⁻¹
α = 80.533 (13)°	T = 296 K
β = 87.519 (14)°	Block, colourless
γ = 83.353 (14)°	0.20 × 0.15 × 0.10 mm
V = 818.9 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2966 independent reflections
Radiation source: fine-focus sealed tube	2530 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ω and φ scans	θ_max = 25.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −6→6
T_min = 0.941, T_max = 0.971	k = −11→11
12059 measured reflections	l = −20→20

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0537P)² + 0.289P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.110	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 0.40 e Å⁻³
2966 reflections	Δρ_min = −0.26 e Å⁻³
228 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015)
0 restraints	Extinction coefficient: 0.015 (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	0.13628 (9)	0.55026 (6)	0.09398 (3)	0.01783 (18)
Cl1	0.76563 (10)	1.05603 (6)	−0.41113 (3)	0.02857 (19)
O1	−0.2181 (3)	1.11191 (15)	−0.14801 (9)	0.0188 (4)
N1	−0.2122 (3)	0.76902 (19)	0.06190 (10)	0.0169 (4)
N2	−0.0436 (3)	0.77957 (18)	−0.00135 (10)	0.0149 (4)
N3	0.3040 (3)	0.69994 (18)	−0.05952 (10)	0.0158 (4)
C1	0.2608 (4)	0.3316 (3)	0.48434 (13)	0.0254 (5)
H1A	0.3880	0.3909	0.4910	0.038*
H1B	0.3278	0.2319	0.4766	0.038*
H1C	0.1580	0.3249	0.5325	0.038*
C2	0.1165 (4)	0.4061 (2)	0.41000 (12)	0.0182 (5)
C3	−0.0867 (4)	0.3460 (2)	0.38955 (13)	0.0194 (5)
H3	−0.1379	0.2620	0.4234	0.023*
C4	−0.2144 (4)	0.4091 (2)	0.31943 (12)	0.0170 (5)
H4	−0.3490	0.3668	0.3070	0.020*
C5	−0.1425 (4)	0.5349 (2)	0.26779 (12)	0.0164 (5)
C6	0.0587 (4)	0.5973 (2)	0.28907 (13)	0.0187 (5)
H6	0.1082	0.6825	0.2559	0.022*
C7	0.1852 (4)	0.5335 (2)	0.35916 (13)	0.0183 (5)
H7	0.3182	0.5768	0.3722	0.022*
C8	−0.2861 (4)	0.6024 (2)	0.19192 (13)	0.0202 (5)
H8A	−0.3853	0.5279	0.1800	0.024*
H8B	−0.3928	0.6887	0.2045	0.024*
C9	−0.1409 (4)	0.6527 (2)	0.11621 (12)	0.0171 (5)
C10	0.1526 (4)	0.6762 (2)	0.00375 (12)	0.0159 (5)
C11	−0.0221 (4)	0.8823 (2)	−0.07365 (12)	0.0152 (4)
C12	−0.2119 (4)	1.0071 (2)	−0.09103 (13)	0.0174 (5)
H12	−0.3429	1.0065	−0.0545	0.021*
C13	0.1975 (4)	0.8283 (2)	−0.10865 (12)	0.0153 (5)
C14	0.3268 (4)	0.8852 (2)	−0.18484 (12)	0.0157 (4)
C15	0.2369 (4)	1.0111 (3)	−0.24086 (13)	0.0242 (5)
H15	0.0863	1.0608	−0.2313	0.029*
C16	0.3697 (4)	1.0622 (3)	−0.31028 (14)	0.0257 (5)
H16	0.3084	1.1459	−0.3471	0.031*
C17	0.5944 (4)	0.9882 (2)	−0.32487 (13)	0.0198 (5)
C18	0.6866 (4)	0.8621 (2)	−0.27129 (13)	0.0185 (5)
H18	0.8365	0.8122	−0.2816	0.022*
C19	0.5524 (4)	0.8117 (2)	−0.20223 (13)	0.0171 (5)
H19	0.6135	0.7266	−0.1663	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0166 (3)	0.0178 (3)	0.0168 (3)	0.0008 (2)	−0.0021 (2)	0.0024 (2)
Cl1	0.0260 (4)	0.0312 (3)	0.0236 (3)	0.0007 (2)	0.0075 (2)	0.0052 (2)
O1	0.0177 (8)	0.0161 (8)	0.0209 (8)	0.0003 (6)	−0.0028 (6)	0.0018 (6)
N1	0.0156 (10)	0.0195 (9)	0.0147 (9)	−0.0018 (7)	−0.0001 (7)	−0.0003 (7)
N2	0.0126 (10)	0.0169 (9)	0.0148 (9)	−0.0014 (7)	−0.0014 (7)	−0.0011 (7)
N3	0.0155 (10)	0.0146 (9)	0.0160 (9)	−0.0001 (7)	−0.0027 (7)	0.0002 (7)
C1	0.0276 (14)	0.0288 (12)	0.0171 (11)	0.0048 (10)	−0.0011 (10)	−0.0007 (9)
C2	0.0189 (12)	0.0200 (11)	0.0138 (10)	0.0065 (8)	0.0032 (9)	−0.0037 (8)
C3	0.0230 (13)	0.0156 (11)	0.0169 (11)	0.0009 (8)	0.0053 (9)	0.0013 (8)
C4	0.0155 (12)	0.0185 (11)	0.0171 (11)	−0.0013 (8)	0.0027 (9)	−0.0044 (8)
C5	0.0141 (12)	0.0188 (11)	0.0146 (10)	0.0026 (8)	0.0008 (8)	−0.0014 (8)
C6	0.0172 (12)	0.0172 (11)	0.0198 (11)	−0.0003 (8)	0.0041 (9)	0.0003 (9)
C7	0.0143 (12)	0.0217 (11)	0.0191 (11)	0.0002 (8)	0.0000 (9)	−0.0051 (9)
C8	0.0140 (12)	0.0238 (12)	0.0205 (11)	−0.0014 (8)	−0.0010 (9)	0.0026 (9)
C9	0.0148 (12)	0.0197 (11)	0.0169 (11)	−0.0012 (8)	−0.0045 (9)	−0.0024 (8)
C10	0.0151 (12)	0.0140 (10)	0.0183 (11)	−0.0002 (8)	−0.0033 (9)	−0.0022 (8)
C11	0.0162 (12)	0.0165 (10)	0.0123 (10)	−0.0026 (8)	−0.0017 (8)	0.0006 (8)
C12	0.0132 (12)	0.0197 (11)	0.0197 (11)	−0.0016 (8)	−0.0012 (9)	−0.0044 (9)
C13	0.0143 (11)	0.0153 (10)	0.0165 (11)	−0.0008 (8)	−0.0062 (8)	−0.0024 (8)
C14	0.0166 (12)	0.0156 (10)	0.0157 (10)	−0.0027 (8)	−0.0027 (8)	−0.0038 (8)
C15	0.0180 (13)	0.0289 (13)	0.0216 (12)	0.0060 (9)	0.0020 (9)	0.0015 (10)
C16	0.0210 (13)	0.0272 (12)	0.0227 (12)	0.0059 (9)	−0.0001 (10)	0.0079 (9)
C17	0.0212 (13)	0.0228 (11)	0.0149 (11)	−0.0023 (9)	0.0003 (9)	−0.0015 (9)
C18	0.0157 (12)	0.0181 (11)	0.0212 (11)	0.0027 (8)	0.0010 (9)	−0.0049 (9)
C19	0.0181 (12)	0.0133 (10)	0.0193 (11)	0.0007 (8)	−0.0033 (9)	−0.0017 (8)

Geometric parameters (Å, º) top

S1—C10	1.724 (2)	C5—C8	1.521 (3)
S1—C9	1.772 (2)	C6—C7	1.390 (3)
Cl1—C17	1.749 (2)	C6—H6	0.9300
O1—C12	1.218 (2)	C7—H7	0.9300
N1—C9	1.299 (3)	C8—C9	1.498 (3)
N1—N2	1.378 (2)	C8—H8A	0.9700
N2—C10	1.355 (3)	C8—H8B	0.9700
N2—C11	1.395 (3)	C11—C13	1.408 (3)
N3—C10	1.323 (3)	C11—C12	1.458 (3)
N3—C13	1.389 (2)	C12—H12	0.9300
C1—C2	1.518 (3)	C13—C14	1.472 (3)
C1—H1A	0.9600	C14—C19	1.401 (3)
C1—H1B	0.9600	C14—C15	1.400 (3)
C1—H1C	0.9600	C15—C16	1.383 (3)
C2—C7	1.390 (3)	C15—H15	0.9300
C2—C3	1.395 (3)	C16—C17	1.388 (3)
C3—C4	1.393 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.384 (3)
C4—C5	1.391 (3)	C18—C19	1.382 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.401 (3)	C19—H19	0.9300

C10—S1—C9	87.97 (10)	H8A—C8—H8B	107.5
C9—N1—N2	108.08 (16)	N1—C9—C8	122.86 (19)
C10—N2—N1	118.52 (17)	N1—C9—S1	116.07 (16)
C10—N2—C11	108.08 (17)	C8—C9—S1	121.03 (15)
N1—N2—C11	133.36 (17)	N3—C10—N2	113.00 (18)
C10—N3—C13	104.36 (16)	N3—C10—S1	137.61 (15)
C2—C1—H1A	109.5	N2—C10—S1	109.37 (15)
C2—C1—H1B	109.5	N2—C11—C13	103.37 (17)
H1A—C1—H1B	109.5	N2—C11—C12	117.73 (19)
C2—C1—H1C	109.5	C13—C11—C12	138.89 (19)
H1A—C1—H1C	109.5	O1—C12—C11	127.2 (2)
H1B—C1—H1C	109.5	O1—C12—H12	116.4
C7—C2—C3	117.96 (19)	C11—C12—H12	116.4
C7—C2—C1	121.3 (2)	N3—C13—C11	111.17 (18)
C3—C2—C1	120.7 (2)	N3—C13—C14	117.41 (18)
C2—C3—C4	121.3 (2)	C11—C13—C14	131.42 (18)
C2—C3—H3	119.4	C19—C14—C15	117.89 (19)
C4—C3—H3	119.4	C19—C14—C13	118.83 (18)
C5—C4—C3	120.6 (2)	C15—C14—C13	123.27 (19)
C5—C4—H4	119.7	C16—C15—C14	120.7 (2)
C3—C4—H4	119.7	C16—C15—H15	119.6
C4—C5—C6	118.18 (19)	C14—C15—H15	119.6
C4—C5—C8	119.60 (19)	C15—C16—C17	119.9 (2)
C6—C5—C8	122.20 (19)	C15—C16—H16	120.1
C7—C6—C5	120.8 (2)	C17—C16—H16	120.1
C7—C6—H6	119.6	C18—C17—C16	120.8 (2)
C5—C6—H6	119.6	C18—C17—Cl1	119.38 (17)
C2—C7—C6	121.1 (2)	C16—C17—Cl1	119.84 (16)
C2—C7—H7	119.4	C19—C18—C17	118.9 (2)
C6—C7—H7	119.4	C19—C18—H18	120.5
C9—C8—C5	115.50 (18)	C17—C18—H18	120.5
C9—C8—H8A	108.4	C18—C19—C14	121.79 (19)
C5—C8—H8A	108.4	C18—C19—H19	119.1
C9—C8—H8B	108.4	C14—C19—H19	119.1
C5—C8—H8B	108.4

C9—N1—N2—C10	−0.5 (2)	C9—S1—C10—N2	−0.02 (15)
C9—N1—N2—C11	−177.9 (2)	C10—N2—C11—C13	0.5 (2)
C7—C2—C3—C4	1.4 (3)	N1—N2—C11—C13	178.12 (18)
C1—C2—C3—C4	−177.03 (18)	C10—N2—C11—C12	−178.46 (17)
C2—C3—C4—C5	−0.2 (3)	N1—N2—C11—C12	−0.9 (3)
C3—C4—C5—C6	−1.1 (3)	N2—C11—C12—O1	175.43 (19)
C3—C4—C5—C8	−179.56 (19)	C13—C11—C12—O1	−3.1 (4)
C4—C5—C6—C7	1.1 (3)	C10—N3—C13—C11	0.1 (2)
C8—C5—C6—C7	179.56 (19)	C10—N3—C13—C14	179.35 (17)
C3—C2—C7—C6	−1.4 (3)	N2—C11—C13—N3	−0.4 (2)
C1—C2—C7—C6	177.07 (19)	C12—C11—C13—N3	178.2 (2)
C5—C6—C7—C2	0.1 (3)	N2—C11—C13—C14	−179.49 (19)
C4—C5—C8—C9	−139.6 (2)	C12—C11—C13—C14	−0.8 (4)
C6—C5—C8—C9	41.9 (3)	N3—C13—C14—C19	−2.5 (3)
N2—N1—C9—C8	−177.12 (17)	C11—C13—C14—C19	176.5 (2)
N2—N1—C9—S1	0.5 (2)	N3—C13—C14—C15	178.33 (18)
C5—C8—C9—N1	−146.1 (2)	C11—C13—C14—C15	−2.7 (3)
C5—C8—C9—S1	36.4 (3)	C19—C14—C15—C16	−1.1 (3)
C10—S1—C9—N1	−0.27 (17)	C13—C14—C15—C16	178.0 (2)
C10—S1—C9—C8	177.37 (18)	C14—C15—C16—C17	0.0 (4)
C13—N3—C10—N2	0.2 (2)	C15—C16—C17—C18	0.9 (3)
C13—N3—C10—S1	−178.12 (18)	C15—C16—C17—Cl1	−178.23 (18)
N1—N2—C10—N3	−178.50 (16)	C16—C17—C18—C19	−0.8 (3)
C11—N2—C10—N3	−0.5 (2)	Cl1—C17—C18—C19	178.40 (15)
N1—N2—C10—S1	0.3 (2)	C17—C18—C19—C14	−0.4 (3)
C11—N2—C10—S1	178.32 (13)	C15—C14—C19—C18	1.3 (3)
C9—S1—C10—N3	178.4 (2)	C13—C14—C19—C18	−177.90 (18)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1	0.93	2.20	3.047 (3)	151
C19—H19···N3	0.93	2.42	2.788 (3)	103
C19—H19···S1ⁱ	0.93	2.83	3.733 (2)	165
C6—H6···O1ⁱⁱ	0.93	2.46	3.384 (3)	170
C18—H18···Cgⁱ	0.93	2.92	3.648 (12)	136

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

Acknowledgements

The authors are grateful to Professor T. N. Guru Row, Indian Institute of Science and DST India, for the data collection on the CCD facility. GNA thanks MSRIT for encouragement.

References

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Volume 72| Part 10| October 2016| Pages 1460-1462

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

The crystal structure of 6-(4-chloro­phen­yl)-2-(4-methyl­benz­yl)imidazo[2,1-b][1,3,4]thia­diazole-5-carbaldehyde

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

The crystal structure of 6-(4-chlorophenyl)-2-(4-methylbenzyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde

3. Supramolecular features