3-Bromo-7-meth-oxy-2-phenyl-imidazo[2,1-b][1,3]benzothia-zole.

In the title mol-ecule, C16H11BrN2OS, the central imidazo[2,1-b][1,3]benzothia-zole tricycle is essentially planar (r.m.s. deviation = 0.021 Å). The terminal phenyl ring is twisted at 36.18 (5)° from the mean plane of the tricycle. In the crystal, pairs of eak C-H⋯O hydrogen bonds link mol-ecules into centrosymmetric dimers, which are further packed into stacks along the a axis.

Related literature

For applications of imidazo[2,1-b][1,3]benzothia­zoles, see: Mase et al. (1988 ▶); Ager et al. (1988 ▶); Barchéchath et al. (2005 ▶); Kumbhare et al. (2011 ▶); Yousefi et al. (2011 ▶); Chandak et al. (2013 ▶). For the crystal structures of related compounds, see: Landreau et al. (2002 ▶); Adib et al. (2008 ▶); Fun, Asik et al. (2011 ▶); Fun, Hemamalini et al. (2011 ▶).

Experimental

Crystal data

C16H11BrN2OS

M = 359.24

Monoclinic,

a = 3.8346 (4) Å

b = 9.4848 (11) Å

c = 37.236 (4) Å

β = 91.810 (2)°

V = 1353.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.19 mm−1

T = 100 K

0.35 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.402, T max = 0.646

17224 measured reflections

3924 independent reflections

3578 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.070

S = 1.00

3924 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.95 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813006582/cv5391sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006582/cv5391Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006582/cv5391Isup3.cml

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

C16H11BrN2OS	F(000) = 720
Mr = 359.24	Dx = 1.763 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9814 reflections
a = 3.8346 (4) Å	θ = 2.2–30.5°
b = 9.4848 (11) Å	µ = 3.19 mm−1
c = 37.236 (4) Å	T = 100 K
β = 91.810 (2)°	Needle, colourless
V = 1353.6 (3) Å3	0.35 × 0.15 × 0.15 mm
Z = 4

Bruker APEXII CCD diffractometer	3924 independent reflections
Radiation source: fine-focus sealed tube	3578 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 30.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −5→5
Tmin = 0.402, Tmax = 0.646	k = −13→13
17224 measured reflections	l = −52→52

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0196P)2 + 2.89P] where P = (Fo2 + 2Fc2)/3
3924 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.95 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
Br1	−0.02456 (5)	0.18794 (2)	0.820287 (5)	0.01435 (6)
O1	0.7765 (4)	−0.18472 (16)	0.97119 (4)	0.0169 (3)
N1	0.3136 (5)	0.49917 (19)	0.88973 (5)	0.0132 (3)
C2	0.1687 (5)	0.4553 (2)	0.85658 (5)	0.0128 (4)
C3	0.1626 (5)	0.3103 (2)	0.85500 (5)	0.0132 (4)
N4	0.3079 (4)	0.26156 (18)	0.88734 (4)	0.0114 (3)
C4A	0.4010 (5)	0.1337 (2)	0.90429 (5)	0.0108 (3)
C5	0.3563 (5)	−0.0040 (2)	0.89273 (5)	0.0122 (4)
H5	0.2447	−0.0235	0.8701	0.015*
C6	0.4774 (5)	−0.1141 (2)	0.91473 (6)	0.0140 (4)
H6	0.4476	−0.2091	0.9071	0.017*
C7	0.6429 (5)	−0.0847 (2)	0.94802 (5)	0.0123 (4)
C8	0.6842 (5)	0.0541 (2)	0.96019 (5)	0.0131 (4)
H8	0.7929	0.0739	0.9829	0.016*
C8A	0.5618 (5)	0.1615 (2)	0.93805 (5)	0.0122 (4)
S9	0.59204 (13)	0.34210 (5)	0.947997 (13)	0.01341 (10)
C9A	0.3926 (5)	0.3811 (2)	0.90637 (5)	0.0120 (4)
C10	0.0582 (5)	0.5587 (2)	0.82933 (5)	0.0130 (4)
C11	−0.0888 (5)	0.6869 (2)	0.83961 (6)	0.0154 (4)
H11	−0.1203	0.7057	0.8644	0.018*
C12	−0.1889 (6)	0.7866 (2)	0.81419 (6)	0.0192 (4)
H12	−0.2904	0.8729	0.8216	0.023*
C13	−0.1415 (6)	0.7611 (2)	0.77781 (6)	0.0198 (4)
H13	−0.2092	0.8298	0.7604	0.024*
C14	0.0052 (6)	0.6347 (3)	0.76713 (6)	0.0189 (4)
H14	0.0374	0.6168	0.7423	0.023*
C15	0.1053 (5)	0.5339 (2)	0.79261 (6)	0.0159 (4)
H15	0.2062	0.4477	0.7851	0.019*
C16	0.7532 (6)	−0.3284 (2)	0.96000 (6)	0.0161 (4)
H16A	0.8656	−0.3888	0.9783	0.024*
H16B	0.8708	−0.3400	0.9372	0.024*
H16C	0.5073	−0.3551	0.9568	0.024*

	U11	U22	U33	U12	U13	U23
Br1	0.01465 (9)	0.01602 (10)	0.01221 (9)	−0.00152 (7)	−0.00252 (6)	−0.00246 (7)
O1	0.0232 (7)	0.0110 (7)	0.0161 (7)	0.0009 (6)	−0.0046 (6)	0.0000 (5)
N1	0.0148 (8)	0.0134 (8)	0.0114 (7)	−0.0011 (6)	0.0001 (6)	−0.0007 (6)
C2	0.0129 (8)	0.0144 (9)	0.0111 (8)	−0.0006 (7)	0.0002 (7)	−0.0001 (7)
C3	0.0132 (8)	0.0143 (9)	0.0121 (8)	−0.0011 (7)	−0.0012 (7)	−0.0025 (7)
N4	0.0121 (7)	0.0119 (8)	0.0102 (7)	0.0002 (6)	−0.0009 (6)	−0.0007 (6)
C4A	0.0097 (8)	0.0134 (9)	0.0091 (8)	−0.0004 (7)	−0.0005 (6)	0.0004 (7)
C5	0.0109 (8)	0.0141 (9)	0.0116 (8)	−0.0005 (7)	−0.0015 (7)	−0.0014 (7)
C6	0.0130 (9)	0.0117 (9)	0.0171 (9)	−0.0011 (7)	−0.0006 (7)	−0.0016 (7)
C7	0.0120 (8)	0.0138 (9)	0.0111 (8)	−0.0003 (7)	0.0004 (7)	0.0018 (7)
C8	0.0136 (8)	0.0149 (9)	0.0107 (8)	−0.0020 (7)	0.0001 (7)	−0.0007 (7)
C8A	0.0114 (8)	0.0125 (9)	0.0127 (8)	−0.0008 (7)	−0.0001 (7)	−0.0015 (7)
S9	0.0176 (2)	0.0104 (2)	0.0120 (2)	−0.00075 (17)	−0.00341 (17)	−0.00098 (16)
C9A	0.0124 (8)	0.0129 (9)	0.0106 (8)	−0.0018 (7)	−0.0006 (7)	−0.0020 (7)
C10	0.0109 (8)	0.0157 (9)	0.0125 (8)	−0.0019 (7)	−0.0016 (7)	0.0012 (7)
C11	0.0148 (9)	0.0150 (9)	0.0163 (9)	−0.0012 (8)	0.0001 (7)	0.0002 (7)
C12	0.0168 (10)	0.0143 (10)	0.0262 (11)	0.0000 (8)	−0.0028 (8)	0.0027 (8)
C13	0.0168 (10)	0.0213 (10)	0.0210 (10)	−0.0025 (8)	−0.0032 (8)	0.0092 (8)
C14	0.0186 (10)	0.0250 (11)	0.0130 (9)	−0.0025 (9)	−0.0020 (8)	0.0044 (8)
C15	0.0130 (8)	0.0184 (10)	0.0164 (9)	−0.0005 (7)	0.0005 (7)	0.0031 (8)
C16	0.0188 (9)	0.0112 (9)	0.0182 (9)	0.0008 (8)	−0.0022 (8)	−0.0009 (7)

Br1—C3	1.864 (2)	C8—H8	0.9500
O1—C7	1.371 (2)	C8A—S9	1.756 (2)
O1—C16	1.427 (2)	S9—C9A	1.746 (2)
N1—C9A	1.311 (3)	C10—C11	1.398 (3)
N1—C2	1.401 (2)	C10—C15	1.404 (3)
C2—C3	1.377 (3)	C11—C12	1.384 (3)
C2—C10	1.465 (3)	C11—H11	0.9500
C3—N4	1.390 (2)	C12—C13	1.394 (3)
N4—C9A	1.370 (3)	C12—H12	0.9500
N4—C4A	1.408 (3)	C13—C14	1.388 (3)
C4A—C5	1.385 (3)	C13—H13	0.9500
C4A—C8A	1.407 (3)	C14—C15	1.392 (3)
C5—C6	1.397 (3)	C14—H14	0.9500
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.403 (3)	C16—H16A	0.9800
C6—H6	0.9500	C16—H16B	0.9800
C7—C8	1.399 (3)	C16—H16C	0.9800
C8—C8A	1.383 (3)
C7—O1—C16	117.30 (16)	C9A—S9—C8A	89.72 (10)
C9A—N1—C2	104.00 (17)	N1—C9A—N4	114.52 (17)
C3—C2—N1	109.89 (17)	N1—C9A—S9	133.52 (16)
C3—C2—C10	129.46 (18)	N4—C9A—S9	111.95 (15)
N1—C2—C10	120.63 (18)	C11—C10—C15	118.53 (19)
C2—C3—N4	106.81 (17)	C11—C10—C2	120.19 (18)
C2—C3—Br1	131.09 (16)	C15—C10—C2	121.25 (19)
N4—C3—Br1	121.94 (15)	C12—C11—C10	120.8 (2)
C9A—N4—C3	104.77 (17)	C12—C11—H11	119.6
C9A—N4—C4A	115.35 (16)	C10—C11—H11	119.6
C3—N4—C4A	139.80 (17)	C11—C12—C13	120.3 (2)
C5—C4A—N4	130.27 (17)	C11—C12—H12	119.9
C5—C4A—C8A	120.03 (18)	C13—C12—H12	119.9
N4—C4A—C8A	109.70 (17)	C14—C13—C12	119.7 (2)
C4A—C5—C6	119.16 (18)	C14—C13—H13	120.2
C4A—C5—H5	120.4	C12—C13—H13	120.2
C6—C5—H5	120.4	C13—C14—C15	120.2 (2)
C5—C6—C7	120.13 (19)	C13—C14—H14	119.9
C5—C6—H6	119.9	C15—C14—H14	119.9
C7—C6—H6	119.9	C14—C15—C10	120.5 (2)
O1—C7—C8	114.26 (17)	C14—C15—H15	119.8
O1—C7—C6	124.62 (18)	C10—C15—H15	119.8
C8—C7—C6	121.12 (18)	O1—C16—H16A	109.5
C8A—C8—C7	117.81 (18)	O1—C16—H16B	109.5
C8A—C8—H8	121.1	H16A—C16—H16B	109.5
C7—C8—H8	121.1	O1—C16—H16C	109.5
C8—C8A—C4A	121.72 (18)	H16A—C16—H16C	109.5
C8—C8A—S9	125.00 (16)	H16B—C16—H16C	109.5
C4A—C8A—S9	113.27 (15)
C9A—N1—C2—C3	0.9 (2)	N4—C4A—C8A—C8	−178.98 (18)
C9A—N1—C2—C10	−177.60 (18)	C5—C4A—C8A—S9	−179.60 (15)
N1—C2—C3—N4	−0.5 (2)	N4—C4A—C8A—S9	0.2 (2)
C10—C2—C3—N4	177.8 (2)	C8—C8A—S9—C9A	178.51 (19)
N1—C2—C3—Br1	174.83 (15)	C4A—C8A—S9—C9A	−0.68 (16)
C10—C2—C3—Br1	−6.9 (4)	C2—N1—C9A—N4	−0.9 (2)
C2—C3—N4—C9A	0.0 (2)	C2—N1—C9A—S9	177.88 (18)
Br1—C3—N4—C9A	−175.90 (14)	C3—N4—C9A—N1	0.6 (2)
C2—C3—N4—C4A	−176.4 (2)	C4A—N4—C9A—N1	178.04 (18)
Br1—C3—N4—C4A	7.7 (3)	C3—N4—C9A—S9	−178.45 (14)
C9A—N4—C4A—C5	−179.7 (2)	C4A—N4—C9A—S9	−1.0 (2)
C3—N4—C4A—C5	−3.5 (4)	C8A—S9—C9A—N1	−177.9 (2)
C9A—N4—C4A—C8A	0.5 (2)	C8A—S9—C9A—N4	0.95 (15)
C3—N4—C4A—C8A	176.6 (2)	C3—C2—C10—C11	146.1 (2)
N4—C4A—C5—C6	179.2 (2)	N1—C2—C10—C11	−35.7 (3)
C8A—C4A—C5—C6	−1.0 (3)	C3—C2—C10—C15	−35.6 (3)
C4A—C5—C6—C7	−0.2 (3)	N1—C2—C10—C15	142.5 (2)
C16—O1—C7—C8	−178.10 (18)	C15—C10—C11—C12	0.6 (3)
C16—O1—C7—C6	1.8 (3)	C2—C10—C11—C12	178.9 (2)
C5—C6—C7—O1	−178.68 (19)	C10—C11—C12—C13	−0.6 (3)
C5—C6—C7—C8	1.2 (3)	C11—C12—C13—C14	0.3 (3)
O1—C7—C8—C8A	178.87 (18)	C12—C13—C14—C15	−0.1 (3)
C6—C7—C8—C8A	−1.1 (3)	C13—C14—C15—C10	0.2 (3)
C7—C8—C8A—C4A	−0.1 (3)	C11—C10—C15—C14	−0.4 (3)
C7—C8—C8A—S9	−179.27 (15)	C2—C10—C15—C14	−178.7 (2)
C5—C4A—C8A—C8	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.95	2.56	3.465 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.95	2.56	3.465 (3)	158

Symmetry code: (i) .