3-{[6-(4-Chloro-phen-yl)imidazo[2,1-b][1,3,4]thia-diazol-2-yl]meth-yl}-1,2-benzoxazole.

In the title compound, C(18)H(11)ClN(4)OS, the benzisoxazole and imidazothia-diazole rings are inclined at an angle of 23.81 (7)° with respect to each other. The imidazothia-diazole and chloro-phenyl rings make a dihedral angle of 27.34 (3)°. In the crystal, inter-molecular C-H⋯N inter-actions generate a chain along the c axis and C-H⋯O inter-actions form centrosymmetric dimers resulting in an R(2) (2)(26) graph-set motif. Moreover, the C-H⋯N and S⋯N [3.206 (4) Å] inter-actions links the mol-ecules into R(7) ring motifs. The packing is further stabilized by π-π stacking inter-actions between the thia-diazole rings with a shortest centroid-centroid distance of 3.497 (3) Å. In addition, C-H⋯π inter-actions are observed in the crystal structure.

Related literature

For the preparation of the title compound see: Lamani et al. (2009 ▶). For the biological activity of benzisoxazole derivatives, see: Priya et al. (2005 ▶). For the use of five-membered heterocyclic ring 1,3,4-thia­diazo­les in the design of compounds, see: Katritzky (1984) ▶; Diamond & Sevrain (2003a ▶,b ▶); Nakao et al. (2002a ▶,b ▶). For related structures, see: Sun & Zhang (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. 1995 ▶)

Experimental

Crystal data

C18H11ClN4OS

M = 366.83

Monoclinic,

a = 38.419 (7) Å

b = 5.7761 (10) Å

c = 14.772 (3) Å

β = 108.004 (5)°

V = 3117.5 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.39 mm−1

T = 123 K

0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan Bruker Smart Apex T min = 0.933, T max = 0.940

8822 measured reflections

3379 independent reflections

2587 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.185

S = 1.31

3379 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.58 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1996) ▶; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004582/gw2098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004582/gw2098Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H11ClN4OS	F(000) = 1504
Mr = 366.83	Dx = 1.563 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3379 reflections
a = 38.419 (7) Å	θ = 2.2–27.0°
b = 5.7761 (10) Å	µ = 0.39 mm−1
c = 14.772 (3) Å	T = 123 K
β = 108.004 (5)°	Block, yellow
V = 3117.5 (10) Å3	0.18 × 0.16 × 0.16 mm
Z = 8

Bruker SMART APEX CCD detector diffractometer	3379 independent reflections
Radiation source: fine-focus sealed tube	2587 reflections with I > 2σ(I)
graphite	Rint = 0.051
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan Bruker Smart Apex	h = −46→48
Tmin = 0.933, Tmax = 0.940	k = −6→7
8822 measured reflections	l = −18→14

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.31	w = 1/[σ2(Fo2) + (0.0894P)2] where P = (Fo2 + 2Fc2)/3
3379 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

Experimental. The compound was synthesized by following the procedure given in Lamani et al., (2009)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
C1	0.19871 (8)	0.2236 (5)	0.1424 (2)	0.0151 (6)
C2	0.16451 (8)	0.1564 (5)	0.1657 (2)	0.0183 (7)
H2A	0.1565	0.0071	0.1366	0.022*
H2B	0.1711	0.1355	0.2341	0.022*
C3	0.13263 (8)	0.3171 (5)	0.1363 (2)	0.0166 (7)
C4	0.25323 (8)	0.4023 (5)	0.1246 (2)	0.0160 (7)
C5	0.28417 (8)	0.0835 (6)	0.1177 (2)	0.0167 (6)
H5	0.2910	−0.0704	0.1157	0.020*
C6	0.30436 (8)	0.2790 (5)	0.1142 (2)	0.0149 (6)
C7	0.34193 (8)	0.2930 (5)	0.1098 (2)	0.0148 (7)
C8	0.35464 (9)	0.4896 (5)	0.0746 (2)	0.0181 (7)
H8	0.3389	0.6139	0.0527	0.022*
C9	0.39034 (9)	0.5024 (5)	0.0718 (2)	0.0192 (7)
H9	0.3986	0.6340	0.0484	0.023*
C10	0.41322 (8)	0.3176 (6)	0.1039 (2)	0.0183 (7)
C11	0.40183 (9)	0.1192 (6)	0.1396 (2)	0.0206 (7)
H11	0.4178	−0.0038	0.1616	0.025*
C12	0.36610 (8)	0.1082 (6)	0.1418 (2)	0.0178 (7)
H12	0.3580	−0.0244	0.1649	0.021*
C13	0.07777 (9)	0.4766 (5)	0.1117 (2)	0.0176 (7)
C14	0.04157 (9)	0.5159 (6)	0.1076 (2)	0.0209 (7)
H14	0.0292	0.6519	0.0834	0.025*
C15	0.02526 (9)	0.3370 (6)	0.1424 (2)	0.0219 (7)
H15	0.0010	0.3519	0.1407	0.026*
C16	0.04440 (8)	0.1336 (6)	0.1800 (3)	0.0212 (7)
H16	0.0326	0.0188	0.2036	0.025*
C17	0.08036 (8)	0.1001 (6)	0.1828 (2)	0.0178 (7)
H17	0.0928	−0.0352	0.2074	0.021*
C18	0.09718 (8)	0.2764 (5)	0.1474 (2)	0.0166 (7)
O1	0.09977 (6)	0.6281 (4)	0.08271 (17)	0.0222 (5)
N1	0.28445 (7)	0.4813 (4)	0.11762 (19)	0.0161 (6)
N2	0.22129 (7)	0.0628 (5)	0.13533 (19)	0.0171 (6)
N3	0.25177 (7)	0.1673 (4)	0.12454 (19)	0.0158 (6)
N4	0.13496 (7)	0.5207 (5)	0.1006 (2)	0.0208 (6)
S1	0.21240 (2)	0.51078 (13)	0.13431 (6)	0.0182 (2)
Cl1	0.45843 (2)	0.33439 (15)	0.10073 (6)	0.0267 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0141 (14)	0.0126 (15)	0.0175 (16)	0.0005 (12)	0.0032 (13)	0.0015 (12)
C2	0.0170 (15)	0.0154 (16)	0.0248 (18)	0.0016 (12)	0.0095 (14)	0.0034 (13)
C3	0.0197 (15)	0.0141 (15)	0.0155 (16)	−0.0028 (12)	0.0049 (13)	−0.0002 (12)
C4	0.0202 (15)	0.0121 (15)	0.0152 (16)	0.0008 (12)	0.0047 (13)	−0.0006 (12)
C5	0.0152 (14)	0.0138 (15)	0.0214 (16)	0.0032 (12)	0.0062 (13)	0.0002 (13)
C6	0.0131 (14)	0.0162 (16)	0.0153 (16)	−0.0011 (12)	0.0042 (13)	0.0011 (12)
C7	0.0137 (14)	0.0156 (16)	0.0159 (16)	−0.0034 (12)	0.0054 (12)	−0.0023 (12)
C8	0.0206 (16)	0.0157 (16)	0.0191 (17)	0.0021 (12)	0.0078 (14)	0.0006 (12)
C9	0.0252 (17)	0.0161 (17)	0.0176 (17)	−0.0052 (13)	0.0086 (14)	−0.0021 (12)
C10	0.0142 (14)	0.0231 (17)	0.0179 (17)	−0.0048 (12)	0.0051 (13)	−0.0056 (13)
C11	0.0231 (16)	0.0177 (17)	0.0220 (18)	0.0049 (13)	0.0084 (14)	−0.0019 (13)
C12	0.0193 (15)	0.0169 (16)	0.0178 (17)	0.0012 (13)	0.0067 (13)	0.0014 (13)
C13	0.0190 (16)	0.0158 (16)	0.0204 (17)	−0.0004 (12)	0.0096 (14)	0.0009 (13)
C14	0.0194 (16)	0.0200 (17)	0.0220 (18)	0.0035 (13)	0.0042 (14)	0.0000 (13)
C15	0.0177 (16)	0.0283 (19)	0.0209 (18)	−0.0017 (13)	0.0077 (14)	−0.0013 (14)
C16	0.0149 (15)	0.0216 (17)	0.0276 (19)	−0.0029 (13)	0.0075 (14)	0.0010 (14)
C17	0.0172 (15)	0.0163 (16)	0.0202 (17)	0.0005 (12)	0.0060 (13)	0.0023 (13)
C18	0.0136 (14)	0.0178 (16)	0.0183 (16)	0.0011 (12)	0.0049 (13)	−0.0003 (13)
O1	0.0200 (11)	0.0167 (12)	0.0325 (14)	0.0044 (9)	0.0120 (11)	0.0055 (10)
N1	0.0114 (12)	0.0167 (14)	0.0206 (14)	0.0006 (10)	0.0054 (11)	−0.0008 (11)
N2	0.0127 (12)	0.0178 (14)	0.0211 (15)	−0.0055 (10)	0.0059 (11)	0.0001 (11)
N3	0.0174 (13)	0.0115 (13)	0.0189 (15)	−0.0012 (10)	0.0059 (11)	0.0013 (10)
N4	0.0147 (13)	0.0244 (16)	0.0251 (16)	0.0015 (11)	0.0087 (12)	0.0010 (12)
S1	0.0184 (4)	0.0124 (4)	0.0257 (5)	−0.0008 (3)	0.0096 (4)	−0.0007 (3)
Cl1	0.0177 (4)	0.0329 (5)	0.0318 (5)	−0.0021 (3)	0.0110 (4)	−0.0057 (4)

C1—N2	1.297 (4)	C9—C10	1.371 (4)
C1—C2	1.508 (4)	C9—H9	0.9300
C1—S1	1.756 (3)	C10—C11	1.387 (5)
C2—C3	1.490 (4)	C10—Cl1	1.755 (3)
C2—H2A	0.9700	C11—C12	1.384 (4)
C2—H2B	0.9700	C11—H11	0.9300
C3—N4	1.304 (4)	C12—H12	0.9300
C3—C18	1.440 (4)	C13—O1	1.374 (4)
C4—N1	1.316 (4)	C13—C14	1.392 (4)
C4—N3	1.358 (4)	C13—C18	1.389 (4)
C4—S1	1.736 (3)	C14—C15	1.387 (5)
C5—C6	1.380 (4)	C14—H14	0.9300
C5—N3	1.369 (4)	C15—C16	1.406 (5)
C5—H5	0.9300	C15—H15	0.9300
C6—N1	1.406 (4)	C16—C17	1.383 (4)
C6—C7	1.468 (4)	C16—H16	0.9300
C7—C12	1.398 (4)	C17—C18	1.392 (4)
C7—C8	1.398 (4)	C17—H17	0.9300
C8—C9	1.387 (4)	O1—N4	1.436 (3)
C8—H8	0.9300	N2—N3	1.370 (3)
N2—C1—C2	119.1 (3)	C12—C11—C10	118.5 (3)
N2—C1—S1	116.7 (2)	C12—C11—H11	120.7
C2—C1—S1	124.0 (2)	C10—C11—H11	120.7
C3—C2—C1	117.9 (3)	C11—C12—C7	121.1 (3)
C3—C2—H2A	107.8	C11—C12—H12	119.4
C1—C2—H2A	107.8	C7—C12—H12	119.4
C3—C2—H2B	107.8	O1—C13—C14	125.8 (3)
C1—C2—H2B	107.8	O1—C13—C18	109.8 (3)
H2A—C2—H2B	107.2	C14—C13—C18	124.4 (3)
N4—C3—C18	112.3 (3)	C13—C14—C15	115.0 (3)
N4—C3—C2	121.8 (3)	C13—C14—H14	122.5
C18—C3—C2	125.9 (3)	C15—C14—H14	122.5
N1—C4—N3	112.7 (3)	C14—C15—C16	121.9 (3)
N1—C4—S1	138.5 (3)	C14—C15—H15	119.1
N3—C4—S1	108.8 (2)	C16—C15—H15	119.1
C6—C5—N3	104.3 (3)	C17—C16—C15	121.6 (3)
C6—C5—H5	127.8	C17—C16—H16	119.2
N3—C5—H5	127.8	C15—C16—H16	119.2
C5—C6—N1	111.2 (3)	C16—C17—C18	117.5 (3)
C5—C6—C7	128.2 (3)	C16—C17—H17	121.3
N1—C6—C7	120.6 (3)	C18—C17—H17	121.3
C12—C7—C8	118.3 (3)	C17—C18—C13	119.7 (3)
C12—C7—C6	120.2 (3)	C17—C18—C3	136.7 (3)
C8—C7—C6	121.5 (3)	C13—C18—C3	103.7 (3)
C9—C8—C7	121.1 (3)	C13—O1—N4	107.6 (2)
C9—C8—H8	119.4	C4—N1—C6	103.5 (2)
C7—C8—H8	119.4	C1—N2—N3	108.1 (3)
C10—C9—C8	118.8 (3)	C4—N3—N2	118.5 (3)
C10—C9—H9	120.6	C4—N3—C5	108.4 (3)
C8—C9—H9	120.6	N2—N3—C5	133.0 (3)
C9—C10—C11	122.1 (3)	C3—N4—O1	106.6 (2)
C9—C10—Cl1	118.8 (2)	C4—S1—C1	87.82 (14)
C11—C10—Cl1	119.1 (2)
N2—C1—C2—C3	−155.9 (3)	O1—C13—C18—C3	−0.9 (3)
S1—C1—C2—C3	30.1 (4)	C14—C13—C18—C3	179.8 (3)
C1—C2—C3—N4	−7.1 (5)	N4—C3—C18—C17	−177.9 (4)
C1—C2—C3—C18	176.2 (3)	C2—C3—C18—C17	−0.9 (6)
N3—C5—C6—N1	−0.8 (3)	N4—C3—C18—C13	1.6 (4)
N3—C5—C6—C7	177.9 (3)	C2—C3—C18—C13	178.6 (3)
C5—C6—C7—C12	−22.8 (5)	C14—C13—O1—N4	179.2 (3)
N1—C6—C7—C12	155.8 (3)	C18—C13—O1—N4	0.0 (3)
C5—C6—C7—C8	157.7 (3)	N3—C4—N1—C6	−0.8 (3)
N1—C6—C7—C8	−23.7 (4)	S1—C4—N1—C6	178.9 (3)
C12—C7—C8—C9	−0.3 (5)	C5—C6—N1—C4	1.0 (3)
C6—C7—C8—C9	179.2 (3)	C7—C6—N1—C4	−177.8 (3)
C7—C8—C9—C10	0.2 (5)	C2—C1—N2—N3	−173.3 (3)
C8—C9—C10—C11	−0.3 (5)	S1—C1—N2—N3	1.1 (3)
C8—C9—C10—Cl1	−179.8 (2)	N1—C4—N3—N2	177.4 (3)
C9—C10—C11—C12	0.5 (5)	S1—C4—N3—N2	−2.5 (3)
Cl1—C10—C11—C12	180.0 (2)	N1—C4—N3—C5	0.3 (4)
C10—C11—C12—C7	−0.7 (5)	S1—C4—N3—C5	−179.5 (2)
C8—C7—C12—C11	0.6 (5)	C1—N2—N3—C4	0.9 (4)
C6—C7—C12—C11	−179.0 (3)	C1—N2—N3—C5	177.1 (3)
O1—C13—C14—C15	−179.3 (3)	C6—C5—N3—C4	0.3 (3)
C18—C13—C14—C15	−0.1 (5)	C6—C5—N3—N2	−176.1 (3)
C13—C14—C15—C16	0.9 (5)	C18—C3—N4—O1	−1.7 (4)
C14—C15—C16—C17	−1.1 (5)	C2—C3—N4—O1	−178.8 (3)
C15—C16—C17—C18	0.4 (5)	C13—O1—N4—C3	1.1 (3)
C16—C17—C18—C13	0.4 (5)	N1—C4—S1—C1	−177.4 (4)
C16—C17—C18—C3	179.8 (4)	N3—C4—S1—C1	2.4 (2)
O1—C13—C18—C17	178.7 (3)	N2—C1—S1—C4	−2.1 (3)
C14—C13—C18—C17	−0.6 (5)	C2—C1—S1—C4	172.1 (3)

Cg1 and Cg2 are the centroids of the C7–C12 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1i	0.93	2.39	3.232 (4)	150
C2—H2B···N1ii	0.97	2.49	3.352 (4)	148
C5—H5···N1iii	0.93	2.60	3.478 (4)	157
C17—H17···Cg1iv	0.93	2.78	3.470 (4)	131
C11—H11···Cg2iv	0.93	2.93	3.548 (4)	126

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C7–C12 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1i	0.93	2.39	3.232 (4)	150
C2—H2B⋯N1ii	0.97	2.49	3.352 (4)	148
C5—H5⋯N1iii	0.93	2.60	3.478 (4)	157
C17—H17⋯Cg1iv	0.93	2.78	3.470 (4)	131
C11—H11⋯Cg2iv	0.93	2.93	3.548 (4)	126

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .