5-Chloro-2-(3,4,5-trimeth-oxy-phen-yl)-1,3-benzothia-zole.

In the title compound, C(16)H(14)ClNO(3)S, the dihedral angle between the almost-planar benzothia-zole ring system [maximum deviation = 0.012 (3) Å] and the aromatic ring of the trimeth-oxy-phenyl group is 15.56 (6)°. In the crystal, the mol-ecules are arranged into layers parallel to the bc plane, held together only by weak van der Waals forces.

Related literature

For the biological activites of benzothia­zole compounds, see: Chohan et al. (2003 ▶); Hutchinson et al. (2002 ▶); Chua et al. (1999 ▶); Burger & Sawhney (1968 ▶); Palmer et al. (1971 ▶). For the crystal structures of related benzothia­zole derivatives, see: Yousuf et al. (2012a ▶,b ▶).

Experimental

Crystal data

C16H14ClNO3S

M = 335.79

Triclinic,

a = 4.0656 (6) Å

b = 7.7855 (11) Å

c = 12.2420 (17) Å

α = 96.263 (3)°

β = 91.380 (3)°

γ = 97.228 (3)°

V = 381.84 (9) Å3

Z = 1

Mo Kα radiation

μ = 0.40 mm−1

T = 273 K

0.52 × 0.15 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.820, T max = 0.965

4277 measured reflections

2816 independent reflections

2621 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.080

S = 1.07

2816 reflections

202 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), with 1402 Friedel pairs

Flack parameter: 0.12 (6)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039372/rz5005sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039372/rz5005Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039372/rz5005Isup3.cml

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

C16H14ClNO3S	Z = 1
Mr = 335.79	F(000) = 174
Triclinic, P1	Dx = 1.460 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.0656 (6) Å	Cell parameters from 2110 reflections
b = 7.7855 (11) Å	θ = 1.7–25.5°
c = 12.2420 (17) Å	µ = 0.40 mm−1
α = 96.263 (3)°	T = 273 K
β = 91.380 (3)°	Plate, colourless
γ = 97.228 (3)°	0.52 × 0.15 × 0.09 mm
V = 381.84 (9) Å3

Bruker SMART APEX CCD diffractometer	2816 independent reflections
Radiation source: fine-focus sealed tube	2621 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −4→4
Tmin = 0.820, Tmax = 0.965	k = −9→9
4277 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0384P)2 + 0.0343P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2816 reflections	Δρmax = 0.14 e Å−3
202 parameters	Δρmin = −0.16 e Å−3
3 restraints	Absolute structure: Flack (1983), with 1402 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.12 (6)

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
S1	0.46803 (14)	0.91830 (7)	0.20220 (5)	0.05768 (18)
Cl1	0.9092 (2)	0.29518 (10)	0.41340 (7)	0.0924 (3)
O1	−0.0441 (5)	1.1670 (2)	−0.14201 (16)	0.0662 (5)
O2	0.0285 (5)	0.9542 (3)	−0.32262 (15)	0.0703 (6)
O3	0.2731 (5)	0.6534 (2)	−0.31396 (14)	0.0670 (5)
N1	0.4815 (5)	0.6095 (3)	0.10078 (16)	0.0510 (5)
C1	0.5921 (6)	0.6053 (3)	0.2087 (2)	0.0483 (6)
C2	0.6876 (8)	0.4599 (4)	0.2507 (2)	0.0603 (7)
H2A	0.6804	0.3539	0.2070	0.072*
C3	0.7927 (7)	0.4782 (4)	0.3588 (2)	0.0616 (7)
C4	0.8097 (7)	0.6314 (4)	0.4269 (2)	0.0651 (8)
H4A	0.8842	0.6378	0.4999	0.078*
C5	0.7142 (8)	0.7758 (4)	0.3852 (2)	0.0651 (8)
H5A	0.7238	0.8813	0.4296	0.078*
C6	0.6036 (6)	0.7615 (3)	0.2761 (2)	0.0499 (6)
C7	0.4065 (5)	0.7623 (3)	0.08620 (18)	0.0443 (5)
C8	0.2955 (5)	0.8118 (3)	−0.01945 (19)	0.0436 (5)
C9	0.1638 (6)	0.9681 (3)	−0.0251 (2)	0.0479 (5)
H9A	0.1328	1.0395	0.0388	0.057*
C10	0.0797 (6)	1.0154 (3)	−0.1272 (2)	0.0495 (6)
C11	0.1223 (6)	0.9078 (3)	−0.2224 (2)	0.0523 (6)
C12	0.2466 (6)	0.7500 (3)	−0.21641 (19)	0.0498 (6)
C13	0.3346 (6)	0.7029 (3)	−0.11455 (19)	0.0496 (5)
H13A	0.4198	0.5984	−0.1100	0.060*
C14	−0.1064 (8)	1.2779 (4)	−0.0479 (3)	0.0675 (7)
H14A	−0.2101	1.3735	−0.0699	0.101*
H14B	0.0992	1.3218	−0.0085	0.101*
H14C	−0.2508	1.2140	−0.0014	0.101*
C15	0.2896 (9)	1.0281 (4)	−0.3824 (2)	0.0788 (9)
H15A	0.2008	1.0805	−0.4421	0.118*
H15B	0.4177	0.9390	−0.4109	0.118*
H15C	0.4291	1.1154	−0.3349	0.118*
C16	0.4033 (8)	0.4926 (4)	−0.3130 (2)	0.0722 (8)
H16A	0.4046	0.4368	−0.3869	0.108*
H16B	0.2677	0.4185	−0.2695	0.108*
H16C	0.6258	0.5138	−0.2820	0.108*

	U11	U22	U33	U12	U13	U23
S1	0.0794 (4)	0.0528 (4)	0.0413 (3)	0.0137 (3)	−0.0038 (3)	0.0030 (3)
Cl1	0.1234 (7)	0.0817 (5)	0.0763 (6)	0.0143 (5)	−0.0310 (5)	0.0349 (4)
O1	0.0760 (13)	0.0611 (11)	0.0673 (12)	0.0246 (10)	−0.0039 (9)	0.0170 (9)
O2	0.0682 (13)	0.0986 (15)	0.0487 (11)	0.0164 (11)	−0.0162 (9)	0.0271 (10)
O3	0.0937 (14)	0.0661 (12)	0.0416 (10)	0.0188 (10)	−0.0110 (9)	0.0008 (8)
N1	0.0684 (13)	0.0473 (11)	0.0368 (10)	0.0066 (9)	−0.0086 (9)	0.0065 (8)
C1	0.0522 (14)	0.0512 (14)	0.0404 (14)	−0.0003 (11)	−0.0047 (10)	0.0100 (11)
C2	0.0778 (18)	0.0532 (15)	0.0498 (15)	0.0072 (13)	−0.0096 (13)	0.0102 (12)
C3	0.0693 (18)	0.0652 (18)	0.0525 (17)	0.0033 (14)	−0.0078 (13)	0.0252 (14)
C4	0.0791 (19)	0.079 (2)	0.0365 (14)	0.0035 (16)	−0.0100 (13)	0.0120 (13)
C5	0.091 (2)	0.0690 (18)	0.0334 (13)	0.0088 (16)	−0.0050 (13)	−0.0003 (12)
C6	0.0539 (14)	0.0541 (15)	0.0407 (13)	0.0045 (11)	−0.0001 (11)	0.0041 (11)
C7	0.0453 (13)	0.0460 (13)	0.0406 (13)	0.0009 (10)	0.0003 (10)	0.0056 (10)
C8	0.0436 (13)	0.0464 (13)	0.0405 (12)	0.0005 (10)	−0.0017 (9)	0.0106 (10)
C9	0.0500 (13)	0.0459 (13)	0.0467 (13)	0.0018 (10)	−0.0002 (10)	0.0058 (10)
C10	0.0435 (13)	0.0495 (13)	0.0579 (15)	0.0050 (10)	−0.0029 (11)	0.0189 (11)
C11	0.0505 (13)	0.0602 (15)	0.0467 (14)	0.0046 (11)	−0.0084 (10)	0.0139 (11)
C12	0.0533 (14)	0.0553 (14)	0.0403 (13)	0.0045 (11)	−0.0052 (10)	0.0076 (10)
C13	0.0573 (14)	0.0473 (13)	0.0446 (13)	0.0069 (11)	−0.0048 (10)	0.0084 (10)
C14	0.0626 (16)	0.0536 (15)	0.088 (2)	0.0140 (12)	0.0002 (14)	0.0110 (13)
C15	0.099 (2)	0.087 (2)	0.0558 (17)	0.0127 (18)	−0.0040 (16)	0.0311 (15)
C16	0.093 (2)	0.0726 (19)	0.0516 (16)	0.0205 (16)	−0.0017 (15)	−0.0021 (14)

S1—C6	1.731 (3)	C5—H5A	0.9300
S1—C7	1.756 (2)	C7—C8	1.466 (3)
Cl1—C3	1.750 (3)	C8—C13	1.388 (3)
O1—C10	1.368 (3)	C8—C9	1.397 (3)
O1—C14	1.410 (4)	C9—C10	1.388 (3)
O2—C11	1.375 (3)	C9—H9A	0.9300
O2—C15	1.403 (3)	C10—C11	1.387 (4)
O3—C12	1.354 (3)	C11—C12	1.395 (3)
O3—C16	1.420 (3)	C12—C13	1.389 (3)
N1—C7	1.294 (3)	C13—H13A	0.9300
N1—C1	1.391 (3)	C14—H14A	0.9600
C1—C2	1.387 (4)	C14—H14B	0.9600
C1—C6	1.388 (3)	C14—H14C	0.9600
C2—C3	1.368 (4)	C15—H15A	0.9600
C2—H2A	0.9300	C15—H15B	0.9600
C3—C4	1.372 (4)	C15—H15C	0.9600
C4—C5	1.378 (4)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.387 (4)	C16—H16C	0.9600
C6—S1—C7	88.87 (11)	C8—C9—H9A	120.4
C10—O1—C14	118.2 (2)	O1—C10—C11	115.7 (2)
C11—O2—C15	114.8 (2)	O1—C10—C9	124.0 (2)
C12—O3—C16	118.1 (2)	C11—C10—C9	120.4 (2)
C7—N1—C1	110.9 (2)	O2—C11—C10	119.6 (2)
C2—C1—C6	120.0 (2)	O2—C11—C12	120.0 (2)
C2—C1—N1	124.9 (2)	C10—C11—C12	120.3 (2)
C6—C1—N1	115.1 (2)	O3—C12—C13	124.8 (2)
C3—C2—C1	117.5 (3)	O3—C12—C11	115.6 (2)
C3—C2—H2A	121.2	C13—C12—C11	119.5 (2)
C1—C2—H2A	121.2	C8—C13—C12	120.0 (2)
C2—C3—C4	123.7 (3)	C8—C13—H13A	120.0
C2—C3—Cl1	118.0 (2)	C12—C13—H13A	120.0
C4—C3—Cl1	118.3 (2)	O1—C14—H14A	109.5
C3—C4—C5	118.8 (3)	O1—C14—H14B	109.5
C3—C4—H4A	120.6	H14A—C14—H14B	109.5
C5—C4—H4A	120.6	O1—C14—H14C	109.5
C4—C5—C6	119.1 (3)	H14A—C14—H14C	109.5
C4—C5—H5A	120.5	H14B—C14—H14C	109.5
C6—C5—H5A	120.5	O2—C15—H15A	109.5
C5—C6—C1	120.9 (2)	O2—C15—H15B	109.5
C5—C6—S1	129.3 (2)	H15A—C15—H15B	109.5
C1—C6—S1	109.74 (19)	O2—C15—H15C	109.5
N1—C7—C8	124.4 (2)	H15A—C15—H15C	109.5
N1—C7—S1	115.40 (17)	H15B—C15—H15C	109.5
C8—C7—S1	120.09 (17)	O3—C16—H16A	109.5
C13—C8—C9	120.5 (2)	O3—C16—H16B	109.5
C13—C8—C7	118.58 (19)	H16A—C16—H16B	109.5
C9—C8—C7	120.9 (2)	O3—C16—H16C	109.5
C10—C9—C8	119.2 (2)	H16A—C16—H16C	109.5
C10—C9—H9A	120.4	H16B—C16—H16C	109.5
C7—N1—C1—C2	179.2 (2)	S1—C7—C8—C9	−15.0 (3)
C7—N1—C1—C6	−0.9 (3)	C13—C8—C9—C10	−1.5 (3)
C6—C1—C2—C3	−0.4 (4)	C7—C8—C9—C10	176.2 (2)
N1—C1—C2—C3	179.5 (3)	C14—O1—C10—C11	177.3 (2)
C1—C2—C3—C4	−0.3 (4)	C14—O1—C10—C9	−3.4 (3)
C1—C2—C3—Cl1	179.2 (2)	C8—C9—C10—O1	−178.5 (2)
C2—C3—C4—C5	0.4 (5)	C8—C9—C10—C11	0.7 (3)
Cl1—C3—C4—C5	−179.1 (2)	C15—O2—C11—C10	100.9 (3)
C3—C4—C5—C6	0.1 (5)	C15—O2—C11—C12	−81.8 (3)
C4—C5—C6—C1	−0.8 (4)	O1—C10—C11—O2	−2.6 (3)
C4—C5—C6—S1	179.7 (2)	C9—C10—C11—O2	178.1 (2)
C2—C1—C6—C5	0.9 (4)	O1—C10—C11—C12	−179.9 (2)
N1—C1—C6—C5	−179.0 (2)	C9—C10—C11—C12	0.7 (3)
C2—C1—C6—S1	−179.5 (2)	C16—O3—C12—C13	−0.7 (4)
N1—C1—C6—S1	0.6 (3)	C16—O3—C12—C11	179.0 (2)
C7—S1—C6—C5	179.4 (3)	O2—C11—C12—O3	1.6 (3)
C7—S1—C6—C1	−0.09 (18)	C10—C11—C12—O3	178.9 (2)
C1—N1—C7—C8	177.3 (2)	O2—C11—C12—C13	−178.8 (2)
C1—N1—C7—S1	0.8 (3)	C10—C11—C12—C13	−1.5 (3)
C6—S1—C7—N1	−0.43 (19)	C9—C8—C13—C12	0.8 (3)
C6—S1—C7—C8	−177.11 (19)	C7—C8—C13—C12	−177.0 (2)
N1—C7—C8—C13	−13.6 (3)	O3—C12—C13—C8	−179.7 (2)
S1—C7—C8—C13	162.74 (17)	C11—C12—C13—C8	0.7 (3)
N1—C7—C8—C9	168.6 (2)