3-{[6-(4-Chloro­phen­yl)imidazo[2,1-b][1,3,4]thia­diazol-2-yl]meth­yl}-1,2-benzoxazole

Banu, A.; Ziaulla, M.; Begum, N.S.; Lamani, R.S.; Khazi, I.M.

doi:10.1107/S1600536811004582

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o617-o618

doi:10.1107/S1600536811004582

Open

access

3-{[6-(4-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl]methyl}-1,2-benzoxazole

Afshan Banu,^a Mohamed Ziaulla,^a Noor Shahina Begum,^a ^* Ravi S. Lamani ^b and I. M. Khazi ^b

^aDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, India, and ^bDepartment of Chemistry, Karnatak University, Dharwad 580 003, India
^*Correspondence e-mail: noorsb@rediffmail.com

(Received 1 January 2011; accepted 7 February 2011; online 12 February 2011)

In the title compound, C₁₈H₁₁ClN₄OS, the benzisoxazole and imidazothiadiazole rings are inclined at an angle of 23.81 (7)° with respect to each other. The imidazothiadiazole and chlorophenyl rings make a dihedral angle of 27.34 (3)°. In the crystal, intermolecular C—H⋯N interactions generate a chain along the c axis and C—H⋯O interactions form centrosymmetric dimers resulting in an R₂²(26) graph-set motif. Moreover, the C—H⋯N and S⋯N [3.206 (4) Å] interactions links the molecules into R(7) ring motifs. The packing is further stabilized by π–π stacking interactions between the thiadiazole rings with a shortest centroid–centroid distance of 3.497 (3) Å. In addition, C—H⋯π interactions 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_r = 366.83
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.185
S = 1.31
3379 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.58 e Å⁻³

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⋯Cg1^iv	0.93	2.78	3.470 (4)	131
C11—H11⋯Cg2^iv	0.93	2.93	3.548 (4)	126
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

Imidazo[2,1-b][1,3,4]thiadiazole derivatives are reported to possess diverse pharmacological properties such as anticancer, antitubercular, antibacterial, antifungal, anticonvulsant, analgesic and antisecretory activities. Moreover, the are known to possess important biological activities (Priya et al., 2005) and are useful in different therapies. Amongst them, five membered heterocyclic ring 1,3,4-thiadiazoles find wide application in designing compounds possessing useful properties (Katritzky et al., 1984; Diamond & Sevrain, 2003a,b; Nakao et al., 2002a,b). Due to the increasing importance of these heterocycles in biological and pharmaceutical fields, new chemical entities were synthesized by incorporating active pharmacophores in a single molecular frame work so as to enhance their biological activities.In the title compound, the benzisoxazole (O1/N4/C3/C13–18) and imidazothiadiazole (S1/N1—N3/C1/C4—C6) rings are individually planar similar to those reported earlier (Sun & Zhang, 2009) with maximum deviations of 0.038 (3)Å for C1 and 0.016 (3)Å for C3 respectively. The mean planes of the benzisoxazole and imidazothiadiazole are inclined at an angle 23.81 (7)° with each other. The imidazothiadiazole and chlorophenyl rings make a dihedral angle of 27.34 (3)°. The thiadiazole moiety displays differences in the bond lengths between S1—C1/S1—C4 [1.756 (3)/1.736 (3)]. This can be attributed to the resonance effects of the imidazole ring which is stronger than that due to thiadiazole group. The crystal structure is stabilized by intermolecular C—H···N, C—H···O and S···N interactions. The C—H···N interaction generates chain like pattern along c axis. The C—H···O interaction forms centrosymmetric head-to-head dimers about inversion centers corresponding to R22(26) graph set motif (Bernstein et al., 1995). The C—H···N interaction along with S···N [3.206 (4) Å]interaction results in a ring motif with a graph set R(7). The molecular packing is further stabilized by π-π stacking interactions between thiadiazole rings (Cg3: centroid of S1/C1/N2/N3/C4) with the shortest centroid—centroid distance 3.497 (3) Å. In addition, π-ring interactions of the type C—H···Cg (Cg being the centroids of rings C7—C12 and C13—C18) are also observed in the crystal structure; details have been given in Table 1.

Related literature top

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 top

The title compound was synthesized by following the procedure reported earlier (Lamani et al., 2009).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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).

Figures top

	Fig. 1. ORTEP (Farrugia, 1997) view of the title compound, showing 50% probability ellipsoids and the atom numbering scheme.
	Fig. 2. A unit cell packing of the title compound depicting the C—H···N, C—H···O and S···N intermolecular interactions with dotted lines. H-atoms not involved in hydrogen bonding have been excluded.

3-{[6-(4-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl]methyl}- 1,2-benzoxazole top

Crystal data top

C₁₈H₁₁ClN₄OS	F(000) = 1504
M_r = 366.83	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0894P)²] where P = (F_o² + 2F_c²)/3
3379 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₁₈H₁₁ClN₄OS	V = 3117.5 (10) Å³
M_r = 366.83	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 38.419 (7) Å	µ = 0.39 mm⁻¹
b = 5.7761 (10) Å	T = 123 K
c = 14.772 (3) Å	0.18 × 0.16 × 0.16 mm
β = 108.004 (5)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	3379 independent reflections
Absorption correction: multi-scan Bruker Smart Apex	2587 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.940	R_int = 0.051
8822 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.185	H-atom parameters constrained
S = 1.31	Δρ_max = 0.74 e Å⁻³
3379 reflections	Δρ_min = −0.58 e Å⁻³
226 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	0.93	2.78	3.470 (4)	131
C11—H11···Cg2^iv	0.93	2.93	3.548 (4)	126

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₁ClN₄OS
M_r	366.83
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	123
a, b, c (Å)	38.419 (7), 5.7761 (10), 14.772 (3)
β (°)	108.004 (5)
V (Å³)	3117.5 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.18 × 0.16 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD detector diffractometer
Absorption correction	Multi-scan Bruker Smart Apex
T_min, T_max	0.933, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	8822, 3379, 2587
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.185, 1.31
No. of reflections	3379
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.58

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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	2.392	3.232 (4)	150
C2—H2B···N1ⁱⁱ	0.97	2.490	3.352 (4)	148
C5—H5···N1ⁱⁱⁱ	0.93	2.600	3.478 (4)	157
C17—H17···Cg1^iv	0.93	2.781	3.470 (4)	131
C11—H11···Cg2^iv	0.93	2.926	3.548 (4)	126

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance and the Department of Science and Technology, (DST), India, for the data-collection facility under the IRHPA–DST program.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. 34, 1555–1573. CrossRef CAS Google Scholar
Bruker (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Diamond, S. & Sevrain, C. (2003a). Chem Abstr. 138, 198554. Google Scholar
Diamond, S. & Sevrain, C. (2003b). PCT Int. Appl. WO 2003016870. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Katritzky, A. R. (1984). In Comprehensive Heterocyclic Chemistry. Oxford: Pergamon. Google Scholar
Lamani, R. S., Shetty, N. S., Ravindra, R. & Khazi, I. A. M. (2009). Eur. J. Med. Chem. 44, 2828–2833. Web of Science CrossRef PubMed CAS Google Scholar
Nakao, H., Matsuzaki, Y., Tohnishi, M., Mmorimoto, M., Fujioka, S., Takemoto, T. & Mamezuka, K. (2002a). Chem Abstr. 137, 384845. Google Scholar
Nakao, H., Matsuzaki, Y., Tohnishi, M., Mmorimoto, M., Fujioka, S., Takemoto, T. & Mamezuka, K. (2002b). PCT Int. Appl. WO 2002092584. Google Scholar
Priya, B. S., Basappa., Swamy, S. N., Rangappa, K. S. (2005). Bioorg. Med. Chem. 13, 2623–2628. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y. & Zhang, H.-H. (2009). Acta Cryst. E65, o1647. Web of Science CSD CrossRef IUCr Journals Google Scholar
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o617-o618

doi:10.1107/S1600536811004582

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-{[6-(4-Chloro­phen­yl)imidazo[2,1-b][1,3,4]thia­diazol-2-yl]meth­yl}-1,2-benzoxazole

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-{[6-(4-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl]methyl}-1,2-benzoxazole