{2-[(1,3-Benzo-thia-zol-2-yl)meth-oxy]-5-bromo-phen-yl}(phen-yl)methanone.

In the title compound, C21H14BrNO2S, the dihedral angle between the planes of the benzo-thia-zole and phenyl-methanone groups is 63.4 (2)°. In the crystal, pairs of C-H⋯N hydrogen bonds link the mol-ecules to form inversion dimers, which are further linked by C-H⋯O inter-actions into chains along the c axis. C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.863 (1) Å] further stabilize the mol-ecular assembly.

Related literature

For background to the applications of benzo­thia­zole derivatives, see: Kelarev et al. (2003 ▶); Rana et al. (2007 ▶); Telvekar et al. (2012 ▶); Saeed et al. (2010 ▶).

Experimental

Crystal data

C21H14BrNO2S

M = 424.30

Monoclinic,

a = 15.1475 (6) Å

b = 7.6501 (3) Å

c = 15.8339 (6) Å

β = 102.105 (3)°

V = 1794.03 (12) Å3

Z = 4

Mo Kα radiation

μ = 2.42 mm−1

T = 292 K

0.23 × 0.21 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Nova) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.606, T max = 0.670

19116 measured reflections

3525 independent reflections

1971 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.120

S = 0.98

3525 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.32 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/S1600536813014086/ff2107sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014086/ff2107Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014086/ff2107Isup3.cml

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

C21H14BrNO2S	F(000) = 856
Mr = 424.30	Dx = 1.571 Mg m−3
Monoclinic, P21/n	Melting point: 407(2) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.7107 Å
a = 15.1475 (6) Å	Cell parameters from 350 reflections
b = 7.6501 (3) Å	θ = 1.0–28.0°
c = 15.8339 (6) Å	µ = 2.42 mm−1
β = 102.105 (3)°	T = 292 K
V = 1794.03 (12) Å3	Block, colourless
Z = 4	0.23 × 0.21 × 0.18 mm

Oxford Diffraction Xcalibur (Eos, Nova) diffractometer	3525 independent reflections
Radiation source: Mova (Mo) X-ray Source	1971 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.088
Detector resolution: 16.0839 pixels mm-1	θmax = 26.0°, θmin = 2.6°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→9
Tmin = 0.606, Tmax = 0.670	l = −19→19
19116 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0408P)2] where P = (Fo2 + 2Fc2)/3
3525 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Experimental. CrysAlisPro (Oxford Diffraction, 2009) 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	0.47887 (4)	0.70720 (7)	0.07925 (3)	0.0671 (2)
S1	−0.04002 (8)	0.33280 (15)	0.17148 (7)	0.0513 (3)
O1	0.1169 (2)	0.4165 (4)	0.11024 (17)	0.0499 (8)
N1	−0.0810 (2)	0.1671 (4)	0.0260 (2)	0.0410 (9)
O2	0.2746 (2)	0.5691 (4)	0.31997 (18)	0.0587 (9)
C6	−0.1521 (3)	0.1423 (5)	0.0671 (3)	0.0389 (10)
C15	0.2206 (3)	0.5983 (5)	0.2529 (3)	0.0395 (10)
C8	0.0664 (3)	0.3039 (5)	0.0468 (3)	0.0424 (11)
H8A	0.1004	0.1981	0.0423	0.051*
H8B	0.0539	0.3614	−0.0090	0.051*
C16	0.1297 (3)	0.6683 (5)	0.2544 (2)	0.0351 (10)
C21	0.0809 (3)	0.7618 (5)	0.1858 (3)	0.0396 (11)
H21	0.1031	0.7750	0.1357	0.048*
C9	0.1982 (3)	0.4790 (5)	0.0998 (3)	0.0397 (10)
C7	−0.0190 (3)	0.2608 (5)	0.0734 (2)	0.0379 (10)
C14	0.2497 (3)	0.5708 (5)	0.1688 (2)	0.0368 (10)
C12	0.3650 (3)	0.6114 (5)	0.0873 (3)	0.0443 (11)
C4	−0.2920 (3)	0.0222 (6)	0.0832 (4)	0.0662 (14)
H4	−0.3432	−0.0445	0.0621	0.079*
C5	−0.2287 (3)	0.0427 (6)	0.0339 (3)	0.0535 (12)
H5	−0.2364	−0.0086	−0.0204	0.064*
C18	0.0136 (3)	0.7221 (6)	0.3328 (3)	0.0554 (13)
H18	−0.0090	0.7088	0.3827	0.066*
C2	−0.2067 (3)	0.1994 (6)	0.1977 (3)	0.0600 (14)
H2	−0.1998	0.2520	0.2517	0.072*
C20	−0.0003 (3)	0.8356 (5)	0.1912 (3)	0.0507 (12)
H20	−0.0325	0.8996	0.1449	0.061*
C1	−0.1411 (3)	0.2200 (5)	0.1478 (3)	0.0438 (11)
C19	−0.0345 (3)	0.8158 (6)	0.2644 (3)	0.0560 (13)
H19	−0.0898	0.8653	0.2676	0.067*
C11	0.3151 (3)	0.5212 (6)	0.0191 (3)	0.0494 (12)
H11	0.3365	0.5058	−0.0313	0.059*
C17	0.0947 (3)	0.6485 (6)	0.3280 (3)	0.0472 (12)
H17	0.1266	0.5846	0.3745	0.057*
C10	0.2324 (3)	0.4533 (5)	0.0261 (3)	0.0470 (12)
H10	0.1990	0.3892	−0.0195	0.056*
C13	0.3333 (3)	0.6361 (5)	0.1623 (3)	0.0436 (11)
H13	0.3682	0.6967	0.2084	0.052*
C3	−0.2813 (4)	0.0995 (7)	0.1649 (4)	0.0688 (15)
H3	−0.3252	0.0830	0.1972	0.083*

	U11	U22	U33	U12	U13	U23
Br1	0.0546 (4)	0.0762 (4)	0.0768 (4)	−0.0116 (3)	0.0282 (3)	−0.0030 (3)
S1	0.0522 (8)	0.0533 (8)	0.0482 (7)	−0.0063 (6)	0.0098 (6)	−0.0133 (6)
O1	0.045 (2)	0.055 (2)	0.0503 (19)	−0.0147 (16)	0.0117 (15)	−0.0175 (15)
N1	0.038 (2)	0.043 (2)	0.038 (2)	0.0021 (18)	0.0004 (18)	0.0006 (17)
O2	0.050 (2)	0.079 (2)	0.0432 (19)	0.0160 (18)	0.0014 (16)	−0.0005 (17)
C6	0.036 (3)	0.034 (2)	0.042 (3)	0.005 (2)	−0.001 (2)	0.000 (2)
C15	0.041 (3)	0.034 (2)	0.040 (3)	−0.006 (2)	0.001 (2)	0.001 (2)
C8	0.045 (3)	0.040 (3)	0.042 (3)	−0.003 (2)	0.007 (2)	−0.006 (2)
C16	0.033 (3)	0.034 (2)	0.036 (2)	−0.004 (2)	0.002 (2)	−0.0054 (19)
C21	0.044 (3)	0.030 (2)	0.044 (3)	−0.001 (2)	0.006 (2)	0.004 (2)
C9	0.035 (3)	0.039 (3)	0.045 (3)	0.002 (2)	0.009 (2)	−0.003 (2)
C7	0.037 (3)	0.037 (2)	0.038 (3)	0.007 (2)	0.004 (2)	0.004 (2)
C14	0.036 (3)	0.040 (3)	0.034 (2)	0.003 (2)	0.0060 (19)	−0.001 (2)
C12	0.042 (3)	0.038 (3)	0.055 (3)	0.005 (2)	0.014 (2)	0.002 (2)
C4	0.040 (3)	0.059 (3)	0.097 (4)	−0.002 (3)	0.010 (3)	0.008 (3)
C5	0.038 (3)	0.052 (3)	0.065 (3)	−0.003 (2)	−0.001 (2)	−0.004 (2)
C18	0.047 (3)	0.081 (4)	0.043 (3)	−0.002 (3)	0.019 (2)	−0.006 (3)
C2	0.058 (4)	0.062 (3)	0.064 (3)	0.006 (3)	0.020 (3)	−0.003 (3)
C20	0.053 (3)	0.036 (3)	0.059 (3)	0.005 (2)	0.002 (3)	0.001 (2)
C1	0.044 (3)	0.037 (3)	0.048 (3)	0.004 (2)	0.004 (2)	0.006 (2)
C19	0.039 (3)	0.057 (3)	0.072 (4)	0.000 (3)	0.011 (3)	−0.011 (3)
C11	0.053 (3)	0.053 (3)	0.044 (3)	0.006 (3)	0.016 (2)	−0.003 (2)
C17	0.051 (3)	0.053 (3)	0.037 (3)	0.001 (2)	0.007 (2)	0.003 (2)
C10	0.049 (3)	0.043 (3)	0.046 (3)	−0.003 (2)	0.006 (2)	−0.012 (2)
C13	0.041 (3)	0.041 (3)	0.047 (3)	−0.002 (2)	0.005 (2)	−0.002 (2)
C3	0.059 (4)	0.062 (4)	0.094 (4)	0.005 (3)	0.034 (3)	0.005 (3)

Br1—C12	1.903 (4)	C12—C11	1.368 (6)
S1—C1	1.729 (5)	C12—C13	1.383 (5)
S1—C7	1.739 (4)	C4—C5	1.366 (6)
O1—C9	1.363 (4)	C4—C3	1.399 (6)
O1—C8	1.418 (4)	C4—H4	0.9300
N1—C7	1.289 (5)	C5—H5	0.9300
N1—C6	1.382 (5)	C18—C17	1.367 (6)
O2—C15	1.218 (4)	C18—C19	1.374 (6)
C6—C1	1.388 (6)	C18—H18	0.9300
C6—C5	1.395 (5)	C2—C3	1.373 (6)
C15—C16	1.482 (5)	C2—C1	1.401 (6)
C15—C14	1.502 (5)	C2—H2	0.9300
C8—C7	1.480 (5)	C20—C19	1.372 (6)
C8—H8A	0.9700	C20—H20	0.9300
C8—H8B	0.9700	C19—H19	0.9300
C16—C21	1.379 (5)	C11—C10	1.382 (5)
C16—C17	1.387 (5)	C11—H11	0.9300
C21—C20	1.373 (6)	C17—H17	0.9300
C21—H21	0.9300	C10—H10	0.9300
C9—C10	1.385 (5)	C13—H13	0.9300
C9—C14	1.393 (5)	C3—H3	0.9300
C14—C13	1.386 (5)
C1—S1—C7	88.2 (2)	C3—C4—H4	119.3
C9—O1—C8	119.5 (3)	C4—C5—C6	118.4 (5)
C7—N1—C6	110.3 (3)	C4—C5—H5	120.8
N1—C6—C1	114.8 (4)	C6—C5—H5	120.8
N1—C6—C5	124.5 (4)	C17—C18—C19	120.3 (4)
C1—C6—C5	120.6 (4)	C17—C18—H18	119.8
O2—C15—C16	120.6 (4)	C19—C18—H18	119.8
O2—C15—C14	118.6 (4)	C3—C2—C1	118.2 (5)
C16—C15—C14	120.8 (4)	C3—C2—H2	120.9
O1—C8—C7	107.9 (3)	C1—C2—H2	120.9
O1—C8—H8A	110.1	C19—C20—C21	120.6 (4)
C7—C8—H8A	110.1	C19—C20—H20	119.7
O1—C8—H8B	110.1	C21—C20—H20	119.7
C7—C8—H8B	110.1	C6—C1—C2	120.6 (4)
H8A—C8—H8B	108.4	C6—C1—S1	110.0 (3)
C21—C16—C17	118.8 (4)	C2—C1—S1	129.4 (4)
C21—C16—C15	121.4 (4)	C20—C19—C18	119.5 (5)
C17—C16—C15	119.7 (4)	C20—C19—H19	120.3
C20—C21—C16	120.3 (4)	C18—C19—H19	120.3
C20—C21—H21	119.9	C12—C11—C10	119.1 (4)
C16—C21—H21	119.9	C12—C11—H11	120.5
O1—C9—C10	124.0 (4)	C10—C11—H11	120.5
O1—C9—C14	116.9 (4)	C18—C17—C16	120.5 (4)
C10—C9—C14	119.0 (4)	C18—C17—H17	119.7
N1—C7—C8	122.1 (4)	C16—C17—H17	119.7
N1—C7—S1	116.6 (3)	C11—C10—C9	121.3 (4)
C8—C7—S1	121.2 (3)	C11—C10—H10	119.3
C13—C14—C9	119.6 (4)	C9—C10—H10	119.3
C13—C14—C15	117.3 (4)	C12—C13—C14	120.1 (4)
C9—C14—C15	123.1 (4)	C12—C13—H13	119.9
C11—C12—C13	120.8 (4)	C14—C13—H13	119.9
C11—C12—Br1	120.0 (3)	C2—C3—C4	120.8 (5)
C13—C12—Br1	119.2 (3)	C2—C3—H3	119.6
C5—C4—C3	121.3 (5)	C4—C3—H3	119.6
C5—C4—H4	119.3
C7—N1—C6—C1	−0.4 (5)	C1—C6—C5—C4	−0.6 (6)
C7—N1—C6—C5	−178.1 (4)	C16—C21—C20—C19	−0.7 (6)
C9—O1—C8—C7	−178.5 (3)	N1—C6—C1—C2	−177.6 (4)
O2—C15—C16—C21	155.4 (4)	C5—C6—C1—C2	0.2 (6)
C14—C15—C16—C21	−21.3 (6)	N1—C6—C1—S1	1.8 (4)
O2—C15—C16—C17	−20.9 (6)	C5—C6—C1—S1	179.5 (3)
C14—C15—C16—C17	162.4 (4)	C3—C2—C1—C6	0.5 (7)
C17—C16—C21—C20	0.9 (6)	C3—C2—C1—S1	−178.7 (4)
C15—C16—C21—C20	−175.5 (4)	C7—S1—C1—C6	−1.9 (3)
C8—O1—C9—C10	6.4 (6)	C7—S1—C1—C2	177.4 (4)
C8—O1—C9—C14	−172.2 (4)	C21—C20—C19—C18	0.5 (7)
C6—N1—C7—C8	178.2 (4)	C17—C18—C19—C20	−0.4 (7)
C6—N1—C7—S1	−1.2 (4)	C13—C12—C11—C10	−0.5 (6)
O1—C8—C7—N1	176.5 (4)	Br1—C12—C11—C10	−179.7 (3)
O1—C8—C7—S1	−4.2 (5)	C19—C18—C17—C16	0.5 (7)
C1—S1—C7—N1	1.8 (3)	C21—C16—C17—C18	−0.7 (6)
C1—S1—C7—C8	−177.5 (3)	C15—C16—C17—C18	175.7 (4)
O1—C9—C14—C13	179.4 (4)	C12—C11—C10—C9	1.8 (6)
C10—C9—C14—C13	0.7 (6)	O1—C9—C10—C11	179.5 (4)
O1—C9—C14—C15	1.6 (6)	C14—C9—C10—C11	−1.9 (6)
C10—C9—C14—C15	−177.1 (4)	C11—C12—C13—C14	−0.6 (6)
O2—C15—C14—C13	−45.6 (5)	Br1—C12—C13—C14	178.6 (3)
C16—C15—C14—C13	131.2 (4)	C9—C14—C13—C12	0.5 (6)
O2—C15—C14—C9	132.2 (4)	C15—C14—C13—C12	178.4 (4)
C16—C15—C14—C9	−50.9 (6)	C1—C2—C3—C4	−0.7 (7)
C3—C4—C5—C6	0.4 (7)	C5—C4—C3—C2	0.3 (8)
N1—C6—C5—C4	176.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···N1i	0.93	2.55	3.398 (6)	152
C5—H5···O2ii	0.93	2.61	3.505 (6)	161
C20—H20···Cg1iii	0.93	2.68	3.459 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/C1/C6/N1/C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯N1i	0.93	2.55	3.398 (6)	152
C5—H5⋯O2ii	0.93	2.61	3.505 (6)	161
C20—H20⋯Cg1iii	0.93	2.68	3.459 (4)	142

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