(2-(Benzo[d]thia­zol-2yl-meth­oxy)-5-chloro­phen­yl)(phen­yl)methanone

Venugopala, K.N.; Nayak, S.K.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536812041888

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3125

doi:10.1107/S1600536812041888

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(2-(Benzo[d]thiazol-2yl-methoxy)-5-chlorophenyl)(phenyl)methanone

K. N. Venugopala,^a ^* Susanta K. Nayak,^b ^* Thavendran Govender,^a Hendrik G. Kruger ^c and Glenn E. M. Maguire ^c

^aSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa, ^bCenter for Nano Science and Technology@Polimi, Istituto Italiano di Tecnologia, Via Pascoli 70/3-20133 Milan, Italy, and ^cSchool of Chemistry and Physics, University of KwaZulu-Natal, Durban 4000, South Africa
^*Correspondence e-mail: venugopala@ukzn.ac.za, nksusa@gmail.com

(Received 21 August 2012; accepted 6 October 2012; online 13 October 2012)

In the title compound, C₂₁H₁₄ClNO₂S, the dihedral angle between the benzothiazole and diphenyl methanone groups is 68.6 (2)°. The crystal structure consists of dimeric units generated by C—H⋯N bonds, further linked by C—H⋯O bonds and C—H⋯π and π–π interactions [centroid–centroiddistance = 3.856 (2) Å], which lead to a criss-cross assembly parallel to (001).

Related literature

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

Experimental

Crystal data

C₂₁H₁₄ClNO₂S
M_r = 379.84
Orthorhombic, P b c a
a = 7.4598 (3) Å
b = 19.3131 (8) Å
c = 24.4002 (9) Å
V = 3515.4 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 173 K
0.22 × 0.16 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.927, T_max = 0.990
52834 measured reflections
3206 independent reflections
2576 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.200
S = 1.30
3206 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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
C17—H17⋯N1ⁱ	0.95	2.56	3.432 (5)	153
C5—H5⋯O2ⁱⁱ	0.95	2.59	3.478 (5)	155
C18—H18⋯Cg1ⁱⁱⁱ	0.95	2.62	3.433 (5)	144
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) x+1, y, z.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; 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, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812041888/bg2479sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041888/bg2479Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812041888/bg2479Isup3.cml

checkCIF report

Comment top

Our interest in the molecular design of the benzothiazole moiety is due to its diverse chemical and biological activities. Benzothiazole derivatives exhibit biological activities as antitumor, antiinflammatory, analgesic, antimicrobial, and potential anti HIV agents etc. Still the variety of biological features of new benzothiazole derivatives are of great scientific interest Rana et al. (2007); Telvekar et al. (2012); Saeed et al. (2010). Here, we report the single-crystal structure of the title compound, C₂₁H₁₄ClNO₂S.

The molecule adopts a conformation with a 68.6 (2)° dihedral angle between the planes of the benzothiazole and diphenyl methanone groups (Fig. 1). The weak C—H···N hydrogen bonds (Table 1, 1st entry) form dimeric units (Fig. 2a), in turn linked by the C—H···O ones (Table 1, 2nd entry) into planar arrays parallel to (001). This 2D structure is reinforced by a C-H···π bond involving the five-membered ring S1/C1/C6/N1/C7 (centroid Cg1) (Table 1, third entry) and a π···π bond between the C10—C14 six-membered ring (centroid Cg2) and the C16—C21 six-membered ring (centroid Cg3), viz., Cg2···Cg3ⁱ, (i): 1/2 + x, 1/2 - y, -z, with an intercentroid distance of 3.856 (2) Å, all these interactions leading to the criss-cross assembly depicted in Fig 2b.

Related literature top

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

Experimental top

To a solution of 2-(chloromethyl)-benzo-thiazole (0.5 g, 0.0027 mol) and (5-chloro-2-hydroxyphenyl)(phenyl)methanone (0.0027 mol) in dry THF, dry potassium carbonate (0.38 g, 0.0027 mol) was added and stirred at room temperature. The reaction mixture was concentrated to remove the solvent, diluted with ethyl acetate, washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated to yield a residue which was purified by column chromatography using ethyl acetate and n-hexane as eluent (7:3, Rf = 0.68) to afford as a white solid product (Yield 70.8%; m. p. 403 (2) K).Suitable crystals for single-crystal X-ray study were obtained by slow evaporation crystallization from ethanol solvent at room temperature.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor,1997); data reduction: DENZO-SMN (Otwinowski & Minor,1997); 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, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme with displacement ellipsoids for non-H atoms at 50% probability level.
	Fig. 2. Packing views of the title compound. (a) Showing in detail the formation of dimers (C—H···N bonds) and their interaction (C—H···O bonds. (b). The criss-cross molecular assembly perpendicular to the c axis.

(2-(Benzo[d]thiazol-2yl-methoxy)-5-chlorophenyl)(phenyl)methanone top

Crystal data top

C₂₁H₁₄ClNO₂S	D_x = 1.435 Mg m⁻³
M_r = 379.84	Melting point: 403(2) K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 560 reflections
a = 7.4598 (3) Å	θ = 1.7–25.3°
b = 19.3131 (8) Å	µ = 0.35 mm⁻¹
c = 24.4002 (9) Å	T = 173 K
V = 3515.4 (2) Å³	Plate, colourless
Z = 8	0.22 × 0.16 × 0.03 mm
F(000) = 1568

Data collection top

Nonius KappaCCD diffractometer	3206 independent reflections
Radiation source: fine-focus sealed tube	2576 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
1.2° ϕ scans and ω scans	θ_max = 25.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −8→8
T_min = 0.927, T_max = 0.990	k = −23→23
52834 measured reflections	l = −29→29

Refinement top

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.200	H-atom parameters constrained
S = 1.30	w = 1/[σ²(F_o²) + (0.071P)² + 8.1626P] where P = (F_o² + 2F_c²)/3
3206 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₁H₁₄ClNO₂S	V = 3515.4 (2) Å³
M_r = 379.84	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.4598 (3) Å	µ = 0.35 mm⁻¹
b = 19.3131 (8) Å	T = 173 K
c = 24.4002 (9) Å	0.22 × 0.16 × 0.03 mm

Data collection top

Nonius KappaCCD diffractometer	3206 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	2576 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.990	R_int = 0.063
52834 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.200	H-atom parameters constrained
S = 1.30	Δρ_max = 0.66 e Å⁻³
3206 reflections	Δρ_min = −0.33 e Å⁻³
235 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.34601 (15)	0.06802 (6)	0.39552 (4)	0.0309 (3)
Cl1	0.68528 (18)	0.27003 (7)	0.68940 (5)	0.0470 (4)
O1	0.4110 (4)	0.11200 (15)	0.50149 (11)	0.0315 (7)
N1	0.1614 (5)	−0.02826 (17)	0.44408 (14)	0.0273 (8)
C6	0.1481 (5)	−0.0405 (2)	0.38812 (17)	0.0270 (9)
C7	0.2577 (5)	0.0259 (2)	0.45299 (16)	0.0256 (9)
C8	0.2953 (6)	0.0542 (2)	0.50881 (16)	0.0276 (9)
H8A	0.1825	0.0688	0.5268	0.033*
H8B	0.3537	0.0187	0.5319	0.033*
O2	0.5685 (4)	0.29934 (15)	0.47346 (12)	0.0373 (8)
C14	0.5686 (5)	0.2081 (2)	0.53676 (16)	0.0245 (9)
C15	0.5962 (5)	0.2376 (2)	0.48050 (17)	0.0258 (9)
C16	0.6632 (5)	0.1936 (2)	0.43523 (16)	0.0240 (9)
C17	0.7650 (5)	0.1344 (2)	0.44537 (16)	0.0266 (9)
H17	0.7872	0.1203	0.4820	0.032*
C13	0.6296 (5)	0.2462 (2)	0.58122 (17)	0.0286 (9)
H13	0.6917	0.2885	0.5753	0.034*
C9	0.4719 (5)	0.1466 (2)	0.54683 (16)	0.0252 (9)
C19	0.8018 (7)	0.1161 (3)	0.34894 (19)	0.0400 (11)
H19	0.8501	0.0899	0.3195	0.048*
C10	0.4403 (6)	0.1248 (2)	0.60021 (17)	0.0305 (9)
H10	0.3735	0.0837	0.6068	0.037*
C18	0.8338 (6)	0.0963 (2)	0.40225 (19)	0.0340 (10)
H18	0.9036	0.0562	0.4095	0.041*
C11	0.5061 (6)	0.1629 (2)	0.64375 (17)	0.0336 (10)
H11	0.4862	0.1477	0.6803	0.040*
C1	0.2398 (6)	0.0070 (2)	0.35491 (17)	0.0286 (9)
C12	0.6004 (6)	0.2229 (2)	0.63404 (17)	0.0301 (10)
C20	0.6980 (7)	0.1747 (3)	0.33833 (18)	0.0409 (12)
H20	0.6730	0.1878	0.3016	0.049*
C5	0.0510 (6)	−0.0945 (2)	0.36427 (19)	0.0347 (10)
H5	−0.0113	−0.1271	0.3863	0.042*
C4	0.0477 (7)	−0.0993 (2)	0.30759 (19)	0.0407 (11)
H4	−0.0177	−0.1357	0.2907	0.049*
C21	0.6322 (6)	0.2134 (2)	0.38092 (18)	0.0340 (10)
H21	0.5647	0.2540	0.3735	0.041*
C2	0.2347 (7)	0.0017 (3)	0.29783 (19)	0.0400 (11)
H2	0.2961	0.0341	0.2754	0.048*
C3	0.1385 (7)	−0.0517 (3)	0.2751 (2)	0.0442 (12)
H3	0.1340	−0.0562	0.2364	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0343 (6)	0.0302 (6)	0.0282 (6)	−0.0080 (5)	0.0014 (4)	0.0005 (4)
Cl1	0.0576 (8)	0.0537 (8)	0.0296 (6)	−0.0104 (6)	−0.0051 (5)	−0.0114 (5)
O1	0.0351 (17)	0.0341 (16)	0.0253 (14)	−0.0140 (14)	0.0015 (12)	−0.0025 (12)
N1	0.0278 (19)	0.0235 (18)	0.0308 (18)	0.0005 (15)	−0.0023 (15)	0.0018 (15)
C6	0.023 (2)	0.026 (2)	0.032 (2)	0.0039 (17)	−0.0003 (17)	−0.0032 (17)
C7	0.021 (2)	0.025 (2)	0.031 (2)	0.0018 (17)	0.0013 (17)	0.0008 (17)
C8	0.028 (2)	0.026 (2)	0.029 (2)	−0.0050 (18)	0.0022 (17)	0.0020 (17)
O2	0.051 (2)	0.0240 (16)	0.0366 (17)	0.0032 (14)	0.0062 (15)	0.0024 (13)
C14	0.023 (2)	0.024 (2)	0.027 (2)	0.0019 (17)	0.0009 (17)	−0.0010 (16)
C15	0.022 (2)	0.025 (2)	0.030 (2)	−0.0031 (17)	−0.0016 (17)	0.0019 (17)
C16	0.023 (2)	0.023 (2)	0.026 (2)	−0.0022 (17)	0.0002 (16)	0.0027 (17)
C17	0.024 (2)	0.028 (2)	0.027 (2)	−0.0004 (18)	−0.0004 (17)	0.0006 (17)
C13	0.026 (2)	0.028 (2)	0.032 (2)	−0.0024 (18)	0.0015 (18)	−0.0033 (17)
C9	0.023 (2)	0.028 (2)	0.025 (2)	0.0003 (17)	−0.0020 (16)	−0.0040 (16)
C19	0.044 (3)	0.043 (3)	0.033 (2)	−0.005 (2)	0.011 (2)	−0.011 (2)
C10	0.030 (2)	0.031 (2)	0.030 (2)	−0.0041 (19)	0.0025 (18)	0.0026 (18)
C18	0.026 (2)	0.032 (2)	0.044 (3)	0.0014 (18)	0.0013 (19)	−0.007 (2)
C11	0.036 (2)	0.041 (3)	0.024 (2)	0.001 (2)	0.0025 (18)	0.0024 (19)
C1	0.025 (2)	0.031 (2)	0.030 (2)	0.0018 (18)	−0.0015 (18)	−0.0024 (18)
C12	0.029 (2)	0.035 (2)	0.026 (2)	0.0031 (19)	−0.0021 (17)	−0.0066 (18)
C20	0.056 (3)	0.044 (3)	0.023 (2)	−0.005 (2)	0.000 (2)	0.004 (2)
C5	0.033 (2)	0.028 (2)	0.043 (3)	−0.001 (2)	−0.002 (2)	−0.005 (2)
C4	0.044 (3)	0.038 (3)	0.040 (3)	−0.004 (2)	−0.008 (2)	−0.014 (2)
C21	0.043 (3)	0.029 (2)	0.030 (2)	−0.002 (2)	−0.004 (2)	0.0076 (18)
C2	0.046 (3)	0.043 (3)	0.030 (2)	−0.006 (2)	0.003 (2)	−0.001 (2)
C3	0.049 (3)	0.053 (3)	0.031 (2)	−0.004 (2)	−0.002 (2)	−0.008 (2)

Geometric parameters (Å, º) top

S1—C1	1.731 (4)	C13—H13	0.9500
S1—C7	1.750 (4)	C9—C10	1.389 (6)
Cl1—C12	1.747 (4)	C19—C18	1.377 (7)
O1—C9	1.370 (5)	C19—C20	1.396 (7)
O1—C8	1.422 (5)	C19—H19	0.9500
N1—C7	1.288 (5)	C10—C11	1.383 (6)
N1—C6	1.389 (5)	C10—H10	0.9500
C6—C5	1.397 (6)	C18—H18	0.9500
C6—C1	1.402 (6)	C11—C12	1.377 (6)
C7—C8	1.494 (6)	C11—H11	0.9500
C8—H8A	0.9900	C1—C2	1.397 (6)
C8—H8B	0.9900	C20—C21	1.371 (6)
O2—C15	1.223 (5)	C20—H20	0.9500
C14—C13	1.388 (6)	C5—C4	1.386 (6)
C14—C9	1.411 (6)	C5—H5	0.9500
C14—C15	1.500 (6)	C4—C3	1.390 (7)
C15—C16	1.480 (6)	C4—H4	0.9500
C16—C17	1.394 (6)	C21—H21	0.9500
C16—C21	1.399 (6)	C2—C3	1.372 (7)
C17—C18	1.383 (6)	C2—H2	0.9500
C17—H17	0.9500	C3—H3	0.9500
C13—C12	1.382 (6)

C1—S1—C7	88.3 (2)	C20—C19—H19	120.1
C9—O1—C8	118.8 (3)	C11—C10—C9	119.9 (4)
C7—N1—C6	110.1 (3)	C11—C10—H10	120.0
N1—C6—C5	125.0 (4)	C9—C10—H10	120.0
N1—C6—C1	115.0 (4)	C19—C18—C17	120.5 (4)
C5—C6—C1	120.0 (4)	C19—C18—H18	119.8
N1—C7—C8	123.8 (4)	C17—C18—H18	119.8
N1—C7—S1	116.9 (3)	C12—C11—C10	119.9 (4)
C8—C7—S1	119.3 (3)	C12—C11—H11	120.1
O1—C8—C7	106.6 (3)	C10—C11—H11	120.1
O1—C8—H8A	110.4	C2—C1—C6	121.0 (4)
C7—C8—H8A	110.4	C2—C1—S1	129.3 (4)
O1—C8—H8B	110.4	C6—C1—S1	109.7 (3)
C7—C8—H8B	110.4	C11—C12—C13	121.0 (4)
H8A—C8—H8B	108.6	C11—C12—Cl1	119.4 (3)
C13—C14—C9	118.6 (4)	C13—C12—Cl1	119.6 (3)
C13—C14—C15	118.0 (4)	C21—C20—C19	120.0 (4)
C9—C14—C15	123.3 (4)	C21—C20—H20	120.0
O2—C15—C16	120.8 (4)	C19—C20—H20	120.0
O2—C15—C14	118.4 (4)	C4—C5—C6	118.3 (4)
C16—C15—C14	120.7 (3)	C4—C5—H5	120.8
C17—C16—C21	118.8 (4)	C6—C5—H5	120.8
C17—C16—C15	121.5 (4)	C5—C4—C3	121.1 (4)
C21—C16—C15	119.6 (4)	C5—C4—H4	119.5
C18—C17—C16	120.2 (4)	C3—C4—H4	119.5
C18—C17—H17	119.9	C20—C21—C16	120.7 (4)
C16—C17—H17	119.9	C20—C21—H21	119.7
C12—C13—C14	120.3 (4)	C16—C21—H21	119.7
C12—C13—H13	119.8	C3—C2—C1	118.2 (4)
C14—C13—H13	119.8	C3—C2—H2	120.9
O1—C9—C10	123.6 (4)	C1—C2—H2	120.9
O1—C9—C14	116.1 (3)	C2—C3—C4	121.4 (4)
C10—C9—C14	120.4 (4)	C2—C3—H3	119.3
C18—C19—C20	119.8 (4)	C4—C3—H3	119.3
C18—C19—H19	120.1

C7—N1—C6—C5	−178.9 (4)	O1—C9—C10—C11	−179.8 (4)
C7—N1—C6—C1	0.2 (5)	C14—C9—C10—C11	−1.0 (6)
C6—N1—C7—C8	178.7 (4)	C20—C19—C18—C17	−0.5 (7)
C6—N1—C7—S1	−0.7 (5)	C16—C17—C18—C19	−0.4 (6)
C1—S1—C7—N1	0.8 (3)	C9—C10—C11—C12	1.0 (7)
C1—S1—C7—C8	−178.6 (3)	N1—C6—C1—C2	−178.7 (4)
C9—O1—C8—C7	−177.9 (3)	C5—C6—C1—C2	0.5 (7)
N1—C7—C8—O1	177.7 (4)	N1—C6—C1—S1	0.4 (5)
S1—C7—C8—O1	−2.9 (5)	C5—C6—C1—S1	179.6 (3)
C13—C14—C15—O2	−42.2 (5)	C7—S1—C1—C2	178.3 (5)
C9—C14—C15—O2	132.7 (4)	C7—S1—C1—C6	−0.6 (3)
C13—C14—C15—C16	135.0 (4)	C10—C11—C12—C13	0.5 (7)
C9—C14—C15—C16	−50.1 (6)	C10—C11—C12—Cl1	−179.2 (3)
O2—C15—C16—C17	152.4 (4)	C14—C13—C12—C11	−2.0 (6)
C14—C15—C16—C17	−24.8 (6)	C14—C13—C12—Cl1	177.7 (3)
O2—C15—C16—C21	−24.3 (6)	C18—C19—C20—C21	1.6 (7)
C14—C15—C16—C21	158.5 (4)	N1—C6—C5—C4	178.8 (4)
C21—C16—C17—C18	0.1 (6)	C1—C6—C5—C4	−0.3 (6)
C15—C16—C17—C18	−176.6 (4)	C6—C5—C4—C3	0.0 (7)
C9—C14—C13—C12	2.0 (6)	C19—C20—C21—C16	−1.9 (7)
C15—C14—C13—C12	177.1 (4)	C17—C16—C21—C20	1.1 (7)
C8—O1—C9—C10	6.1 (6)	C15—C16—C21—C20	177.8 (4)
C8—O1—C9—C14	−172.8 (3)	C6—C1—C2—C3	−0.5 (7)
C13—C14—C9—O1	178.4 (3)	S1—C1—C2—C3	−179.3 (4)
C15—C14—C9—O1	3.6 (6)	C1—C2—C3—C4	0.2 (8)
C13—C14—C9—C10	−0.5 (6)	C5—C4—C3—C2	0.0 (8)
C15—C14—C9—C10	−175.3 (4)

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N1ⁱ	0.95	2.56	3.432 (5)	153
C5—H5···O2ⁱⁱ	0.95	2.59	3.478 (5)	155
C18—H18···Cg1ⁱⁱⁱ	0.95	2.62	3.433 (5)	144

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y−1/2, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄ClNO₂S
M_r	379.84
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	173
a, b, c (Å)	7.4598 (3), 19.3131 (8), 24.4002 (9)
V (Å³)	3515.4 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.22 × 0.16 × 0.03

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.927, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	52834, 3206, 2576
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.200, 1.30
No. of reflections	3206
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.33

Computer programs: COLLECT (Nonius, 1998), DENZO-SMN (Otwinowski & Minor,1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

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

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N1ⁱ	0.9500	2.5600	3.432 (5)	153
C5—H5···O2ⁱⁱ	0.9500	2.5900	3.478 (5)	155
C18—H18···Cg1ⁱⁱⁱ	0.9500	2.6200	3.433 (5)	144

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y−1/2, z; (iii) x+1, y, z.

Acknowledgements

The authors wish to thank the University of KwaZulu-Natal, South Africa, for facilities and Dr Hong Su, Department of Chemistry, University of Cape Town, for the data collection.

References

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Volume 68| Part 11| November 2012| Page o3125

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