[2-(1,3-Benzothia-zol-2-ylmeth-oxy)-5-bromo-phen-yl](4-chloro-phen-yl)methanone.

In the title compound, C21H13BrClNO2S, the dihedral angle between the planes of the benzothia-zole and chloro-phenyl-methanone groups is 71.34 (6)°. In the crystal, weak C-H⋯N hydrogen bonds lead to dimer formation, whereas Br⋯Cl short contacts [3.4966 (11) Å] form infinite chains along the a-axis direction. Further, the C-H⋯O, C-H⋯π and π-π [centroid-centroid distance = 3.865 (2) Å] inter-actions stabilize the three-dimensional network.

Related literature

For background to the applications of benzothia­zole derivatives, see: Rana et al. (2007 ▶); Saeed et al. (2010 ▶); Telvekar et al. (2012 ▶); Venugopala et al. (2012 ▶). For their biological activity, see: Kelarev et al. (2003 ▶). For types of inter­actions involving halogens, see: Nayak et al. (2011 ▶).

Experimental

Crystal data

C21H13BrClNO2S

M = 458.74

Monoclinic,

a = 13.7746 (3) Å

b = 7.4918 (2) Å

c = 18.7016 (7) Å

β = 106.013 (3)°

V = 1855.05 (10) Å3

Z = 4

Mo Kα radiation

μ = 2.49 mm−1

T = 292 K

0.21 × 0.19 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Nova) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.623, T max = 0.865

19324 measured reflections

3645 independent reflections

2451 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.096

S = 1.07

3645 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) ▶ and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049756/go2078sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049756/go2078Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049756/go2078Isup3.cml

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

C21H13BrClNO2S	F(000) = 920
Mr = 458.74	Dx = 1.643 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 450 reflections
a = 13.7746 (3) Å	θ = 1.0–28.0°
b = 7.4918 (2) Å	µ = 2.49 mm−1
c = 18.7016 (7) Å	T = 292 K
β = 106.013 (3)°	Plate, colourless
V = 1855.05 (10) Å3	0.21 × 0.19 × 0.06 mm
Z = 4

Oxford Diffraction Xcalibur (Eos, Nova) diffractometer	3645 independent reflections
Radiation source: Mova (Mo) X-ray Source	2451 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.054
Detector resolution: 16.0839 pixels mm-1	θmax = 26.0°, θmin = 3.0°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→9
Tmin = 0.623, Tmax = 0.865	l = −23→23
19324 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0325P)2 + 0.1234P] where P = (Fo2 + 2Fc2)/3
3645 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Br1	1.04455 (3)	−0.14743 (5)	0.15995 (3)	0.06540 (18)
S1	0.41791 (7)	0.14738 (11)	0.12108 (5)	0.0461 (2)
Cl1	0.28248 (7)	−0.33938 (14)	0.18242 (7)	0.0736 (3)
O1	0.61465 (16)	0.0996 (3)	0.11015 (12)	0.0437 (6)
N1	0.39940 (19)	0.3398 (3)	0.00334 (14)	0.0356 (6)
O2	0.75803 (17)	−0.0576 (3)	0.30851 (13)	0.0563 (7)
C14	0.7576 (2)	−0.0504 (4)	0.18309 (18)	0.0351 (8)
C6	0.3056 (2)	0.3399 (4)	0.01745 (17)	0.0337 (7)
C9	0.7118 (2)	0.0447 (4)	0.11796 (18)	0.0359 (8)
C17	0.5611 (2)	−0.2566 (4)	0.16701 (16)	0.0363 (8)
H17	0.5988	−0.2865	0.1345	0.044*
C16	0.6032 (2)	−0.1492 (4)	0.22765 (17)	0.0320 (7)
C1	0.3006 (2)	0.2404 (4)	0.07985 (17)	0.0393 (8)
C20	0.4476 (2)	−0.1627 (4)	0.26215 (18)	0.0427 (8)
H20	0.4088	−0.1295	0.2935	0.051*
C7	0.4624 (2)	0.2449 (4)	0.05198 (16)	0.0341 (7)
C10	0.7655 (2)	0.0818 (4)	0.06722 (19)	0.0432 (8)
H10	0.7350	0.1464	0.0244	0.052*
C8	0.5692 (2)	0.2169 (4)	0.05054 (18)	0.0416 (8)
H8A	0.5711	0.1649	0.0035	0.050*
H8B	0.6050	0.3298	0.0567	0.050*
C15	0.7089 (2)	−0.0826 (4)	0.24430 (19)	0.0366 (8)
C18	0.4637 (2)	−0.3200 (4)	0.15417 (19)	0.0414 (8)
H18	0.4363	−0.3952	0.1141	0.050*
C5	0.2192 (2)	0.4269 (4)	−0.02485 (18)	0.0432 (8)
H5	0.2210	0.4945	−0.0662	0.052*
C19	0.4081 (2)	−0.2704 (4)	0.20142 (19)	0.0409 (8)
C11	0.8638 (2)	0.0239 (4)	0.0796 (2)	0.0447 (9)
H11	0.8993	0.0471	0.0448	0.054*
C2	0.2111 (3)	0.2240 (5)	0.09968 (19)	0.0507 (9)
H2	0.2083	0.1569	0.1409	0.061*
C21	0.5458 (2)	−0.1054 (4)	0.27540 (18)	0.0409 (8)
H21	0.5743	−0.0360	0.3172	0.049*
C4	0.1317 (3)	0.4104 (5)	−0.0041 (2)	0.0542 (10)
H4	0.0739	0.4687	−0.0317	0.065*
C13	0.8576 (2)	−0.1043 (4)	0.19534 (19)	0.0394 (8)
H13	0.8898	−0.1650	0.2388	0.047*
C12	0.9090 (2)	−0.0684 (4)	0.1436 (2)	0.0454 (9)
C3	0.1270 (3)	0.3092 (5)	0.0570 (2)	0.0572 (10)
H3	0.0661	0.2991	0.0691	0.069*

	U11	U22	U33	U12	U13	U23
Br1	0.0341 (2)	0.0652 (3)	0.0997 (4)	0.00450 (18)	0.0232 (2)	−0.0024 (2)
S1	0.0439 (5)	0.0521 (6)	0.0458 (6)	0.0111 (4)	0.0182 (5)	0.0180 (4)
Cl1	0.0384 (5)	0.0839 (8)	0.0968 (9)	−0.0133 (5)	0.0160 (6)	−0.0076 (6)
O1	0.0339 (12)	0.0514 (14)	0.0502 (15)	0.0117 (10)	0.0188 (12)	0.0197 (11)
N1	0.0365 (15)	0.0345 (15)	0.0351 (16)	0.0021 (12)	0.0087 (13)	0.0025 (12)
O2	0.0474 (15)	0.0796 (18)	0.0373 (15)	−0.0139 (13)	0.0040 (13)	−0.0010 (13)
C14	0.0302 (17)	0.0320 (18)	0.044 (2)	0.0009 (14)	0.0111 (16)	−0.0017 (16)
C6	0.0363 (18)	0.0317 (17)	0.0325 (18)	0.0029 (14)	0.0087 (15)	−0.0003 (15)
C9	0.0304 (17)	0.0326 (18)	0.047 (2)	0.0010 (14)	0.0139 (16)	−0.0020 (15)
C17	0.040 (2)	0.0357 (19)	0.0344 (19)	0.0064 (15)	0.0124 (16)	0.0029 (15)
C16	0.0329 (17)	0.0315 (17)	0.0323 (18)	0.0029 (14)	0.0100 (15)	0.0021 (15)
C1	0.0385 (19)	0.0397 (19)	0.040 (2)	0.0061 (15)	0.0115 (17)	0.0021 (16)
C20	0.039 (2)	0.051 (2)	0.042 (2)	0.0012 (16)	0.0183 (18)	0.0030 (17)
C7	0.0379 (18)	0.0327 (18)	0.0324 (18)	0.0016 (15)	0.0106 (16)	0.0007 (15)
C10	0.041 (2)	0.0414 (19)	0.050 (2)	0.0049 (16)	0.0178 (18)	0.0057 (16)
C8	0.0389 (19)	0.043 (2)	0.044 (2)	0.0073 (16)	0.0132 (17)	0.0108 (17)
C15	0.0364 (18)	0.0324 (17)	0.039 (2)	0.0002 (14)	0.0068 (17)	−0.0007 (15)
C18	0.043 (2)	0.037 (2)	0.042 (2)	−0.0027 (15)	0.0072 (18)	−0.0031 (16)
C5	0.0387 (19)	0.049 (2)	0.039 (2)	0.0038 (17)	0.0068 (17)	0.0043 (16)
C19	0.0290 (18)	0.043 (2)	0.049 (2)	−0.0034 (15)	0.0074 (17)	0.0082 (17)
C11	0.041 (2)	0.044 (2)	0.056 (2)	−0.0013 (16)	0.0252 (19)	−0.0015 (18)
C2	0.048 (2)	0.060 (2)	0.049 (2)	0.0020 (19)	0.021 (2)	0.0089 (19)
C21	0.044 (2)	0.045 (2)	0.0316 (19)	−0.0023 (16)	0.0077 (17)	−0.0041 (15)
C4	0.038 (2)	0.070 (3)	0.050 (2)	0.0113 (19)	0.0049 (19)	−0.003 (2)
C13	0.0322 (18)	0.0383 (19)	0.044 (2)	−0.0004 (14)	0.0048 (17)	0.0014 (15)
C12	0.0314 (18)	0.0378 (19)	0.068 (3)	−0.0006 (15)	0.0156 (19)	−0.0073 (19)
C3	0.038 (2)	0.075 (3)	0.063 (3)	0.004 (2)	0.020 (2)	−0.001 (2)

Br1—C12	1.902 (3)	C20—C19	1.377 (4)
S1—C1	1.733 (3)	C20—H20	0.9300
S1—C7	1.737 (3)	C7—C8	1.493 (4)
Cl1—C19	1.746 (3)	C10—C11	1.380 (4)
O1—C9	1.368 (3)	C10—H10	0.9300
O1—C8	1.422 (3)	C8—H8A	0.9700
N1—C7	1.285 (4)	C8—H8B	0.9700
N1—C6	1.389 (4)	C18—C19	1.371 (4)
O2—C15	1.219 (3)	C18—H18	0.9300
C14—C13	1.392 (4)	C5—C4	1.370 (5)
C14—C9	1.402 (4)	C5—H5	0.9300
C14—C15	1.498 (4)	C11—C12	1.374 (4)
C6—C5	1.395 (4)	C11—H11	0.9300
C6—C1	1.402 (4)	C2—C3	1.370 (5)
C9—C10	1.383 (4)	C2—H2	0.9300
C17—C18	1.380 (4)	C21—H21	0.9300
C17—C16	1.381 (4)	C4—C3	1.388 (5)
C17—H17	0.9300	C4—H4	0.9300
C16—C21	1.385 (4)	C13—C12	1.373 (4)
C16—C15	1.489 (4)	C13—H13	0.9300
C1—C2	1.387 (4)	C3—H3	0.9300
C20—C21	1.375 (4)
C1—S1—C7	88.70 (15)	H8A—C8—H8B	108.5
C9—O1—C8	118.4 (2)	O2—C15—C16	120.2 (3)
C7—N1—C6	110.4 (3)	O2—C15—C14	118.9 (3)
C13—C14—C9	118.6 (3)	C16—C15—C14	120.9 (3)
C13—C14—C15	117.3 (3)	C19—C18—C17	118.9 (3)
C9—C14—C15	123.8 (3)	C19—C18—H18	120.5
N1—C6—C5	125.8 (3)	C17—C18—H18	120.5
N1—C6—C1	114.8 (3)	C4—C5—C6	118.5 (3)
C5—C6—C1	119.4 (3)	C4—C5—H5	120.8
O1—C9—C10	124.0 (3)	C6—C5—H5	120.8
O1—C9—C14	116.0 (3)	C18—C19—C20	121.8 (3)
C10—C9—C14	120.0 (3)	C18—C19—Cl1	119.2 (3)
C18—C17—C16	120.7 (3)	C20—C19—Cl1	119.0 (3)
C18—C17—H17	119.6	C12—C11—C10	119.4 (3)
C16—C17—H17	119.6	C12—C11—H11	120.3
C17—C16—C21	118.9 (3)	C10—C11—H11	120.3
C17—C16—C15	122.1 (3)	C3—C2—C1	118.3 (3)
C21—C16—C15	119.0 (3)	C3—C2—H2	120.8
C2—C1—C6	121.4 (3)	C1—C2—H2	120.8
C2—C1—S1	129.3 (3)	C20—C21—C16	121.2 (3)
C6—C1—S1	109.3 (2)	C20—C21—H21	119.4
C21—C20—C19	118.5 (3)	C16—C21—H21	119.4
C21—C20—H20	120.8	C5—C4—C3	121.8 (3)
C19—C20—H20	120.8	C5—C4—H4	119.1
N1—C7—C8	122.8 (3)	C3—C4—H4	119.1
N1—C7—S1	116.8 (2)	C12—C13—C14	120.4 (3)
C8—C7—S1	120.4 (2)	C12—C13—H13	119.8
C11—C10—C9	120.6 (3)	C14—C13—H13	119.8
C11—C10—H10	119.7	C13—C12—C11	121.0 (3)
C9—C10—H10	119.7	C13—C12—Br1	120.0 (3)
O1—C8—C7	107.2 (2)	C11—C12—Br1	119.0 (3)
O1—C8—H8A	110.3	C2—C3—C4	120.6 (4)
C7—C8—H8A	110.3	C2—C3—H3	119.7
O1—C8—H8B	110.3	C4—C3—H3	119.7
C7—C8—H8B	110.3
C7—N1—C6—C5	−179.0 (3)	C21—C16—C15—C14	−151.8 (3)
C7—N1—C6—C1	0.3 (4)	C13—C14—C15—O2	40.1 (4)
C8—O1—C9—C10	−6.7 (4)	C9—C14—C15—O2	−133.8 (3)
C8—O1—C9—C14	171.5 (3)	C13—C14—C15—C16	−138.1 (3)
C13—C14—C9—O1	−177.8 (3)	C9—C14—C15—C16	48.0 (4)
C15—C14—C9—O1	−4.0 (4)	C16—C17—C18—C19	1.9 (5)
C13—C14—C9—C10	0.5 (4)	N1—C6—C5—C4	178.6 (3)
C15—C14—C9—C10	174.3 (3)	C1—C6—C5—C4	−0.6 (5)
C18—C17—C16—C21	−0.2 (4)	C17—C18—C19—C20	−1.5 (5)
C18—C17—C16—C15	178.3 (3)	C17—C18—C19—Cl1	176.3 (2)
N1—C6—C1—C2	−178.2 (3)	C21—C20—C19—C18	−0.5 (5)
C5—C6—C1—C2	1.1 (5)	C21—C20—C19—Cl1	−178.3 (2)
N1—C6—C1—S1	0.5 (3)	C9—C10—C11—C12	−1.3 (5)
C5—C6—C1—S1	179.8 (2)	C6—C1—C2—C3	−0.5 (5)
C7—S1—C1—C2	177.7 (3)	S1—C1—C2—C3	−178.9 (3)
C7—S1—C1—C6	−0.8 (2)	C19—C20—C21—C16	2.2 (5)
C6—N1—C7—C8	178.9 (3)	C17—C16—C21—C20	−1.8 (5)
C6—N1—C7—S1	−1.0 (3)	C15—C16—C21—C20	179.6 (3)
C1—S1—C7—N1	1.1 (3)	C6—C5—C4—C3	−0.5 (5)
C1—S1—C7—C8	−178.8 (3)	C9—C14—C13—C12	−1.5 (5)
O1—C9—C10—C11	179.0 (3)	C15—C14—C13—C12	−175.7 (3)
C14—C9—C10—C11	0.9 (5)	C14—C13—C12—C11	1.2 (5)
C9—O1—C8—C7	176.2 (2)	C14—C13—C12—Br1	−178.6 (2)
N1—C7—C8—O1	−177.4 (3)	C10—C11—C12—C13	0.3 (5)
S1—C7—C8—O1	2.4 (4)	C10—C11—C12—Br1	180.0 (2)
C17—C16—C15—O2	−148.5 (3)	C1—C2—C3—C4	−0.5 (5)
C21—C16—C15—O2	30.0 (4)	C5—C4—C3—C2	1.1 (6)
C17—C16—C15—C14	29.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.93	2.58	3.446 (4)	156
C17—H17···N1ii	0.93	2.61	3.434 (4)	147
C18—H18···Cg1iii	0.93	2.82	3.666 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the thia­zole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.58	3.446 (4)	156
C17—H17⋯N1ii	0.93	2.61	3.434 (4)	147
C18—H18⋯Cg1iii	0.93	2.82	3.666 (3)	151

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