{2-[(1,3-Benzo-thia-zol-2-yl)meth-oxy]-5-chloro-phen-yl}(4-chloro-phen-yl)methan-one.

In the title compound, C21H13Cl2NO2S, the benzo-thia-zole ring makes dihedral angles of 0.94 (1) and 70.65 (5)° with the 4-chloro-phenyl-methanone unit and the 5-chloro-phenyl ring, respectively. The dihedral angle between the 4-chloro-phenyl-methanone unit and the 5-chloro-phenyl ring is 66.20 (5)°. The crystal structure consists of dimeric units generated by C-H⋯N hydrogen bonds, further linked by C-H⋯O and C-H⋯π inter-actions, leading to a three-dimensional network.

Related literature

For crystal structures of benzo­thia­zole derivatives, see: Venugopala et al. (2012 ▶); Nayak et al. (2013 ▶). For background to the applications of benzo­thia­zole derivatives, see: Rana et al. (2007 ▶); Saeed et al. (2010 ▶); Kelarev et al. (2003 ▶); Telvekar et al. (2012 ▶).

Experimental

Crystal data

C21H13Cl2NO2S

M = 414.29

Monoclinic,

a = 13.6452 (4) Å

b = 7.47005 (19) Å

c = 18.7286 (6) Å

β = 105.772 (3)°

V = 1837.14 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 292 K

0.23 × 0.21 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Nova) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.897, T max = 0.935

18937 measured reflections

3602 independent reflections

2544 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.109

S = 1.08

3602 reflections

241 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016243/lx2286sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016243/lx2286Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016243/lx2286Isup3.cml

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

C21H13Cl2NO2S	F(000) = 848
Mr = 414.29	Dx = 1.498 Mg m−3
Monoclinic, P21/n	Melting point: 448(2) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.7107 Å
a = 13.6452 (4) Å	Cell parameters from 340 reflections
b = 7.47005 (19) Å	θ = 1.0–28.0°
c = 18.7286 (6) Å	µ = 0.48 mm−1
β = 105.772 (3)°	T = 292 K
V = 1837.14 (9) Å3	Plate, colourless
Z = 4	0.23 × 0.21 × 0.14 mm

Oxford Diffraction Xcalibur (Eos, Nova) diffractometer	3602 independent reflections
Radiation source: Mova (Mo) X-ray Source	2544 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.047
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, 2010)	k = −9→9
Tmin = 0.897, Tmax = 0.935	l = −23→22
18937 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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F2) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0429P)2 + 0.3056P] where P = (Fo2 + 2Fc2)/3
3602 reflections	(Δ/σ)max = 0.001
241 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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
Cl1	1.03821 (5)	0.35913 (10)	0.66313 (5)	0.0683 (2)
Cl2	0.27764 (6)	0.15904 (12)	0.68234 (5)	0.0776 (3)
S1	0.41607 (5)	0.64525 (9)	0.62033 (3)	0.0465 (2)
O1	0.61507 (12)	0.6008 (2)	0.61055 (9)	0.0449 (4)
O2	0.75637 (13)	0.4439 (3)	0.80903 (9)	0.0571 (5)
N1	0.39772 (14)	0.8383 (2)	0.50261 (9)	0.0357 (4)
C1	0.29751 (17)	0.7360 (3)	0.57862 (12)	0.0384 (5)
C2	0.20652 (19)	0.7169 (3)	0.59779 (13)	0.0496 (7)
H2	0.2033	0.6494	0.6388	0.060*
C3	0.12177 (14)	0.8006 (3)	0.55448 (11)	0.0551 (7)
H3	0.0600	0.7892	0.5661	0.066*
C4	0.12656 (14)	0.9025 (3)	0.49327 (11)	0.0524 (7)
H4	0.0681	0.9592	0.4652	0.063*
C5	0.21558 (18)	0.9210 (3)	0.47357 (12)	0.0433 (6)
H5	0.2179	0.9891	0.4325	0.052*
C6	0.30286 (17)	0.8354 (3)	0.51649 (11)	0.0344 (5)
C7	0.46196 (17)	0.7448 (3)	0.55169 (11)	0.0335 (5)
C8	0.56983 (17)	0.7178 (3)	0.55111 (12)	0.0410 (6)
H8A	0.5729	0.6658	0.5043	0.049*
H8B	0.6056	0.8315	0.5574	0.049*
C9	0.71332 (16)	0.5456 (3)	0.61952 (12)	0.0359 (5)
C10	0.76869 (18)	0.5827 (3)	0.56916 (13)	0.0423 (6)
H10	0.7387	0.6468	0.5262	0.051*
C11	0.86790 (19)	0.5250 (3)	0.58258 (14)	0.0476 (6)
H11	0.9046	0.5490	0.5485	0.057*
C12	0.91267 (17)	0.4315 (3)	0.64669 (15)	0.0455 (6)
C13	0.85941 (17)	0.3962 (3)	0.69754 (13)	0.0406 (6)
H13	0.8910	0.3356	0.7411	0.049*
C14	0.75846 (16)	0.4504 (3)	0.68441 (12)	0.0352 (5)
C15	0.70758 (17)	0.4179 (3)	0.74501 (13)	0.0364 (5)
C16	0.60070 (17)	0.3519 (3)	0.72806 (11)	0.0328 (5)
C17	0.55910 (17)	0.2434 (3)	0.66717 (12)	0.0375 (5)
H17	0.5975	0.2137	0.6348	0.045*
C18	0.46132 (18)	0.1796 (3)	0.65457 (13)	0.0413 (6)
H18	0.4343	0.1034	0.6148	0.050*
C19	0.40357 (17)	0.2297 (3)	0.70148 (13)	0.0426 (6)
C20	0.44320 (18)	0.3374 (3)	0.76184 (13)	0.0435 (6)
H20	0.4035	0.3705	0.7929	0.052*
C21	0.54231 (18)	0.3957 (3)	0.77580 (12)	0.0388 (6)
H21	0.5704	0.4650	0.8176	0.047*

	U11	U22	U33	U12	U13	U23
Cl1	0.0348 (4)	0.0681 (5)	0.1045 (6)	0.0057 (3)	0.0233 (4)	−0.0048 (4)
Cl2	0.0439 (5)	0.0873 (6)	0.1010 (6)	−0.0192 (4)	0.0186 (4)	−0.0089 (5)
S1	0.0465 (4)	0.0513 (4)	0.0448 (4)	0.0111 (3)	0.0174 (3)	0.0183 (3)
O1	0.0344 (9)	0.0520 (10)	0.0520 (10)	0.0117 (8)	0.0180 (8)	0.0215 (8)
O2	0.0495 (11)	0.0790 (14)	0.0378 (10)	−0.0129 (10)	0.0032 (9)	−0.0004 (9)
N1	0.0373 (11)	0.0370 (11)	0.0321 (10)	0.0027 (8)	0.0084 (9)	0.0035 (8)
C1	0.0397 (14)	0.0370 (13)	0.0398 (13)	0.0046 (10)	0.0131 (11)	0.0034 (10)
C2	0.0507 (17)	0.0545 (16)	0.0502 (15)	0.0031 (13)	0.0245 (13)	0.0062 (13)
C3	0.0427 (16)	0.0652 (18)	0.0626 (18)	0.0036 (13)	0.0231 (14)	0.0006 (14)
C4	0.0386 (15)	0.0629 (18)	0.0525 (16)	0.0123 (13)	0.0068 (13)	0.0026 (13)
C5	0.0421 (15)	0.0465 (14)	0.0390 (14)	0.0040 (11)	0.0068 (12)	0.0054 (11)
C6	0.0379 (14)	0.0325 (12)	0.0327 (12)	−0.0002 (10)	0.0093 (11)	−0.0035 (10)
C7	0.0366 (13)	0.0302 (12)	0.0340 (12)	0.0004 (10)	0.0102 (10)	0.0004 (10)
C8	0.0385 (14)	0.0431 (14)	0.0422 (14)	0.0059 (11)	0.0123 (11)	0.0114 (11)
C9	0.0321 (13)	0.0318 (12)	0.0454 (14)	0.0011 (10)	0.0131 (11)	−0.0007 (10)
C10	0.0433 (15)	0.0406 (14)	0.0468 (14)	−0.0005 (11)	0.0187 (12)	0.0018 (11)
C11	0.0454 (15)	0.0439 (15)	0.0608 (16)	−0.0051 (12)	0.0270 (13)	−0.0046 (13)
C12	0.0309 (13)	0.0403 (14)	0.0673 (17)	−0.0023 (11)	0.0166 (13)	−0.0105 (13)
C13	0.0348 (14)	0.0359 (13)	0.0487 (14)	0.0006 (10)	0.0073 (12)	−0.0020 (11)
C14	0.0320 (13)	0.0300 (12)	0.0433 (13)	−0.0014 (10)	0.0100 (11)	−0.0038 (10)
C15	0.0376 (14)	0.0318 (12)	0.0377 (14)	0.0040 (10)	0.0066 (11)	0.0034 (10)
C16	0.0354 (13)	0.0303 (12)	0.0313 (12)	0.0020 (10)	0.0065 (10)	0.0043 (9)
C17	0.0453 (15)	0.0316 (13)	0.0371 (13)	0.0047 (11)	0.0136 (11)	0.0012 (10)
C18	0.0437 (15)	0.0339 (13)	0.0440 (14)	−0.0028 (11)	0.0078 (12)	−0.0039 (10)
C19	0.0327 (13)	0.0417 (14)	0.0516 (15)	−0.0038 (11)	0.0083 (12)	0.0077 (12)
C20	0.0440 (15)	0.0500 (15)	0.0406 (14)	0.0002 (12)	0.0184 (12)	0.0038 (11)
C21	0.0452 (15)	0.0412 (14)	0.0295 (12)	−0.0018 (11)	0.0094 (11)	−0.0014 (10)

Cl1—C12	1.742 (2)	C9—C10	1.387 (3)
Cl2—C19	1.739 (2)	C9—C14	1.398 (3)
S1—C1	1.732 (2)	C10—C11	1.377 (3)
S1—C7	1.742 (2)	C10—H10	0.9300
O1—C9	1.369 (2)	C11—C12	1.380 (3)
O1—C8	1.418 (3)	C11—H11	0.9300
O2—C15	1.218 (3)	C12—C13	1.372 (3)
N1—C7	1.290 (3)	C13—C14	1.392 (3)
N1—C6	1.388 (3)	C13—H13	0.9300
C1—C2	1.390 (3)	C14—C15	1.502 (3)
C1—C6	1.399 (3)	C15—C16	1.490 (3)
C2—C3	1.370 (3)	C16—C17	1.389 (3)
C2—H2	0.9300	C16—C21	1.389 (3)
C3—C4	1.3923	C17—C18	1.375 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.369 (3)	C18—C19	1.382 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.398 (3)	C19—C20	1.373 (3)
C5—H5	0.9300	C20—C21	1.376 (3)
C7—C8	1.489 (3)	C20—H20	0.9300
C8—H8A	0.9700	C21—H21	0.9300
C8—H8B	0.9700
C1—S1—C7	88.81 (11)	C9—C10—H10	119.9
C9—O1—C8	119.01 (16)	C10—C11—C12	119.9 (2)
C7—N1—C6	110.21 (18)	C10—C11—H11	120.1
C2—C1—C6	121.4 (2)	C12—C11—H11	120.1
C2—C1—S1	129.33 (18)	C13—C12—C11	120.6 (2)
C6—C1—S1	109.22 (17)	C13—C12—Cl1	119.9 (2)
C3—C2—C1	118.0 (2)	C11—C12—Cl1	119.50 (19)
C3—C2—H2	121.0	C12—C13—C14	120.5 (2)
C1—C2—H2	121.0	C12—C13—H13	119.8
C2—C3—C4	121.07 (13)	C14—C13—H13	119.8
C2—C3—H3	119.5	C13—C14—C9	118.9 (2)
C4—C3—H3	119.5	C13—C14—C15	117.2 (2)
C5—C4—C3	121.37 (13)	C9—C14—C15	123.62 (19)
C5—C4—H4	119.3	O2—C15—C16	120.2 (2)
C3—C4—H4	119.3	O2—C15—C14	118.5 (2)
C4—C5—C6	118.6 (2)	C16—C15—C14	121.3 (2)
C4—C5—H5	120.7	C17—C16—C21	119.2 (2)
C6—C5—H5	120.7	C17—C16—C15	121.8 (2)
N1—C6—C5	125.3 (2)	C21—C16—C15	119.0 (2)
N1—C6—C1	115.25 (19)	C18—C17—C16	120.3 (2)
C5—C6—C1	119.5 (2)	C18—C17—H17	119.9
N1—C7—C8	123.36 (19)	C16—C17—H17	119.9
N1—C7—S1	116.50 (17)	C17—C18—C19	119.4 (2)
C8—C7—S1	120.13 (16)	C17—C18—H18	120.3
O1—C8—C7	107.34 (17)	C19—C18—H18	120.3
O1—C8—H8A	110.2	C20—C19—C18	121.1 (2)
C7—C8—H8A	110.2	C20—C19—Cl2	119.58 (19)
O1—C8—H8B	110.2	C18—C19—Cl2	119.27 (19)
C7—C8—H8B	110.2	C19—C20—C21	119.3 (2)
H8A—C8—H8B	108.5	C19—C20—H20	120.4
O1—C9—C10	123.5 (2)	C21—C20—H20	120.4
O1—C9—C14	116.45 (18)	C20—C21—C16	120.6 (2)
C10—C9—C14	120.0 (2)	C20—C21—H21	119.7
C11—C10—C9	120.2 (2)	C16—C21—H21	119.7
C11—C10—H10	119.9
C7—S1—C1—C2	177.6 (2)	C10—C11—C12—Cl1	−179.97 (18)
C7—S1—C1—C6	−0.48 (17)	C11—C12—C13—C14	1.6 (3)
C6—C1—C2—C3	−0.9 (4)	Cl1—C12—C13—C14	−178.83 (17)
S1—C1—C2—C3	−178.70 (18)	C12—C13—C14—C9	−1.7 (3)
C1—C2—C3—C4	−0.3 (3)	C12—C13—C14—C15	−175.9 (2)
C2—C3—C4—C5	0.85 (17)	O1—C9—C14—C13	−177.90 (19)
C3—C4—C5—C6	−0.2 (3)	C10—C9—C14—C13	0.7 (3)
C7—N1—C6—C5	−179.2 (2)	O1—C9—C14—C15	−4.1 (3)
C7—N1—C6—C1	0.3 (3)	C10—C9—C14—C15	174.5 (2)
C4—C5—C6—N1	178.5 (2)	C13—C14—C15—O2	40.4 (3)
C4—C5—C6—C1	−0.9 (3)	C9—C14—C15—O2	−133.5 (2)
C2—C1—C6—N1	−178.0 (2)	C13—C14—C15—C16	−138.4 (2)
S1—C1—C6—N1	0.2 (2)	C9—C14—C15—C16	47.7 (3)
C2—C1—C6—C5	1.5 (3)	O2—C15—C16—C17	−148.8 (2)
S1—C1—C6—C5	179.73 (18)	C14—C15—C16—C17	30.0 (3)
C6—N1—C7—C8	178.5 (2)	O2—C15—C16—C21	29.2 (3)
C6—N1—C7—S1	−0.7 (2)	C14—C15—C16—C21	−152.1 (2)
C1—S1—C7—N1	0.70 (18)	C21—C16—C17—C18	−0.2 (3)
C1—S1—C7—C8	−178.48 (19)	C15—C16—C17—C18	177.7 (2)
C9—O1—C8—C7	176.11 (18)	C16—C17—C18—C19	2.3 (3)
N1—C7—C8—O1	−176.87 (19)	C17—C18—C19—C20	−2.1 (3)
S1—C7—C8—O1	2.3 (3)	C17—C18—C19—Cl2	176.40 (17)
C8—O1—C9—C10	−6.9 (3)	C18—C19—C20—C21	−0.2 (4)
C8—O1—C9—C14	171.7 (2)	Cl2—C19—C20—C21	−178.73 (18)
O1—C9—C10—C11	179.0 (2)	C19—C20—C21—C16	2.3 (3)
C14—C9—C10—C11	0.4 (3)	C17—C16—C21—C20	−2.1 (3)
C9—C10—C11—C12	−0.6 (4)	C15—C16—C21—C20	179.9 (2)
C10—C11—C12—C13	−0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.93	2.56	3.429 (3)	157
C17—H17···N1ii	0.93	2.62	3.442 (3)	148
C18—H18···Cgiii	0.93	2.83	3.682 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.56	3.429 (3)	157
C17—H17⋯N1ii	0.93	2.62	3.442 (3)	148
C18—H18⋯Cg iii	0.93	2.83	3.682 (2)	152

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