(2E)-1-(2,4-Dimethyl­quinolin-3-yl)-3-(thio­phen-2-yl)prop-2-en-1-one

Prasath, R.; Bhavana, P.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811031485

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages o2283-o2284

doi:10.1107/S1600536811031485

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(2E)-1-(2,4-Dimethylquinolin-3-yl)-3-(thiophen-2-yl)prop-2-en-1-one †

R. Prasath,^a P. Bhavana,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, BITS, Pilani – K. K. Birla Goa Campus, Goa 403 726, India, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 4 August 2011; accepted 4 August 2011; online 11 August 2011)

Two independent but virtually identical molecules comprise the asymmetric unit in the title compound, C₁₈H₁₅NOS. With reference to the quinolin-3-yl group, the 3-(thiophen-2-yl)prop-2-en-1-one residue is almost perpendicular, with all but the carbonyl O atom lying to one side of the plane. This conformation is reflected by the C—C—C—C torsion angles of −102.2 (3) and 81.1 (3)° in the two independent molecules. The dihedral angle formed between the 13 non-H atoms directly associated with the quinolin-3-yl group and the thiophen-2-yl ring is 87.70 (11)° [83.85 (10)° for the second independent molecule]. The presence of C—H⋯O, C—H⋯N and π–π interactions [centroid–centroid distance = 3.5590 (12) Å] lead to supramolecular chains along the c-axis direction. These are connected along the a-axis direction by C—H⋯π interactions. The resultant supramolecular layers stack along the b axis.

Related literature

For background details and biological applications of quinolines, see: Kalluraya & Sreenivasa (1998 ); Xiang et al. (2006 ). For the biological activity of chalcones, see: Dimmock et al. (1999 ); Siddiqui et al. (2008 ).

Experimental

Crystal data

C₁₈H₁₅NOS
M_r = 293.37
Monoclinic, P 2₁ /n
a = 10.4935 (4) Å
b = 23.8464 (8) Å
c = 11.5464 (4) Å
β = 93.756 (3)°
V = 2883.07 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.947, T_max = 0.967
14916 measured reflections
6427 independent reflections
4075 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.160
S = 1.03
6427 reflections
409 parameters
182 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C31–C36 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2ⁱ	0.95	2.51	3.391 (3)	154
C6—H6⋯O2	0.95	2.55	3.382 (3)	146
C23—H23⋯N1ⁱⁱ	0.95	2.50	3.382 (3)	154
C24—H24⋯O1	0.95	2.48	3.330 (3)	149
C12—H12c⋯Cg1ⁱⁱⁱ	0.98	2.67	142	4 (1)
C26—H26c⋯Cg2^iv	0.98	2.67	143	4 (1)
Symmetry codes: (i) x, y, z-1; (ii) x, y, z+1; (iii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iv) $[x-{\script{3\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); 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 (Farrugia, 1997 ), DIAMOND (Brandenburg, 2006 ) and Qmol (Gans & Shalloway, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031485/hg5075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031485/hg5075Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031485/hg5075Isup3.cml

checkCIF report

Comment top

Chalcone derivatives have attracted wide attention owing to their occurrence in natural products and biologically active compounds (Dimmock et al., 1999; Siddiqui et al., 2008). Quinoline chalcone analogues have also gained notice due to their bioactivities such as anti-plasmodial, anti-microbial, anti-malarial and anti-cancer activities (Kalluraya & Sreenivasa, 1998; Xiang et al., 2006). It was in this context that the title compound, (I), was investigated.

Two independent molecules comprise the crystallographic asymmetric unit of (I), Fig. 1, and as may be seen from Fig. 2, the molecular conformations are almost identical with a minor variation in the relative orientations of the terminal thiophenyl rings. The 3-(thiophen-2-yl)prop-2-en-1-one residue is almost normal to the least-squares plane through the quinolin-3-yl group and three bound C substituents (r.m.s. deviations = 0.028 and 0.035 Å, respectively), i.e. 13 non-C atoms. This conformation is reflected in the C6—C7—C10—C9 and C24—C25—C28—C27 torsion angles of -102.2 (3) and 81.1 (3) °, respectively. With reference to the aforementioned quinolin-3-yl plane, the carbonyl-O lies to one side and the remaining atoms of the 3-(thiophen-2-yl)prop-2-en-1-one residue to the other. The dihedral angles formed between the quinolin-3-yl and thiophen-2-yl rings are 87.70 (11) and 83.85 (10) °, respectively. The conformation about the ethene bond is E [C5═C6 = 1.345 (3) Å, and C23═C24 = 1.341 (3) Å].

In the crystal packing, supramolecular layers are formed in the ac plane owing to a combination of C—H···O, C—H···N, C—H···π and π–π interactions, Table 1 and Fig. 3. The two independent molecules comprising the asymmetric unit are linked via the C—H···O interactions, to form an eight-membered {···O═C₂H}₂ synthon. These are linked into a supramolecular chain along the c axis by C—H···N and π–π interactions. The C—H···π contacts extend in the a direction. Layers stack along the b axis as illustrated in Fig. 4.

Related literature top

For background details and biological applications of quinolines, see: Kalluraya & Sreenivasa (1998); Xiang et al. (2006). For the biological activity of chalcones, see: Dimmock et al. (1999); Siddiqui et al. (2008).

Experimental top

A mixture of 3-acetyl-2,4-dimethylquinoline (0.01 M), 2-thiophenecarboxaldehyde (0.01 M) and a catalytic amount of KOH in distilled ethanol was stirred for 12 h at room temperature. The resulting mixture was neutralized with dilute acetic acid. The solid that formed was filtered, dried and purified by column chromatography using 1:3 mixture of ethyl acetate and hexane. Recrystallization was by slow evaporation of its acetone solution which yielded colourless needles. M.pt. 418–420 K. Yield: 82%.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structures of the two independent molecules comprising the asymmetric unit of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Overlay diagram of the two independent molecules comprising the asymmetric unit of (I). The first independent molecule (with the S1 atom) is shown in red.
	Fig. 3. Assembly of molecules in the ac plane in (I) mediated by C—H···O (orange dashed lines), C—H···N (blue), C—H···π (purple) and π–π (pink) interactions.
	Fig. 4. A view in projection down the a axis of the crystal packing in (I) highlighting the stacking of layers along the b axis.

(2E)-1-(2,4-Dimethylquinolin-3-yl)-3-(thiophen-2-yl)prop-2-en-1-one top

Crystal data top

C₁₈H₁₅NOS	F(000) = 1232
M_r = 293.37	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4109 reflections
a = 10.4935 (4) Å	θ = 2.5–29.2°
b = 23.8464 (8) Å	µ = 0.22 mm⁻¹
c = 11.5464 (4) Å	T = 100 K
β = 93.756 (3)°	Block, colourless
V = 2883.07 (18) Å³	0.25 × 0.20 × 0.15 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	6427 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4075 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.040
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −30→22
T_min = 0.947, T_max = 0.967	l = −14→11
14916 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0713P)² + 0.299P] where P = (F_o² + 2F_c²)/3
6427 reflections	(Δ/σ)_max < 0.001
409 parameters	Δρ_max = 0.56 e Å⁻³
182 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₈H₁₅NOS	V = 2883.07 (18) Å³
M_r = 293.37	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.4935 (4) Å	µ = 0.22 mm⁻¹
b = 23.8464 (8) Å	T = 100 K
c = 11.5464 (4) Å	0.25 × 0.20 × 0.15 mm
β = 93.756 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	6427 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4075 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.967	R_int = 0.040
14916 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	182 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.03	Δρ_max = 0.56 e Å⁻³
6427 reflections	Δρ_min = −0.46 e Å⁻³
409 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.30670 (9)	0.05958 (3)	0.34043 (8)	0.0224 (3)	0.765 (2)
S2	1.08225 (8)	0.05541 (3)	0.60970 (7)	0.0228 (3)	0.814 (2)
S1'	0.2891 (5)	0.10382 (16)	0.1135 (4)	0.0224 (3)	0.235 (2)
S2'	1.1144 (6)	0.10712 (19)	0.8273 (5)	0.0228 (3)	0.186 (2)
O1	0.83016 (16)	0.07720 (7)	0.36269 (14)	0.0240 (4)
O2	0.56274 (16)	0.07794 (7)	0.59472 (14)	0.0259 (4)
N1	0.87096 (18)	0.13639 (8)	0.00826 (16)	0.0182 (4)
N2	0.52776 (18)	0.14083 (8)	0.94581 (16)	0.0181 (4)
C1	0.1610 (3)	0.06381 (10)	0.2659 (3)	0.0246 (9)	0.765 (2)
H1	0.0835	0.0521	0.2965	0.029*	0.765 (2)
C2	0.1682 (4)	0.08583 (10)	0.1576 (3)	0.0284 (9)	0.765 (2)
H2	0.0971	0.0912	0.1035	0.034*	0.765 (2)
C3	0.2925 (5)	0.09927 (16)	0.1371 (4)	0.0253 (14)	0.765 (2)
H3	0.3144	0.1157	0.0661	0.030*	0.765 (2)
C1'	0.1608 (11)	0.0803 (2)	0.1824 (9)	0.0246 (9)	0.235 (2)
H1'	0.0755	0.0803	0.1492	0.029*	0.235 (2)
C2'	0.1964 (10)	0.0612 (2)	0.2923 (9)	0.0284 (9)	0.235 (2)
H2'	0.1379	0.0468	0.3442	0.034*	0.235 (2)
C3'	0.3256 (10)	0.0652 (2)	0.3189 (7)	0.0253 (14)	0.235 (2)
H3'	0.3678	0.0542	0.3906	0.030*	0.235 (2)
C4	0.3847 (2)	0.08728 (9)	0.22700 (19)	0.0194 (5)
C5	0.5200 (2)	0.09698 (9)	0.22462 (19)	0.0176 (5)
H5	0.5482	0.1144	0.1569	0.021*
C6	0.6106 (2)	0.08403 (10)	0.3082 (2)	0.0202 (5)
H6	0.5863	0.0667	0.3776	0.024*
C7	0.7457 (2)	0.09599 (9)	0.29473 (19)	0.0179 (5)
C8	0.8360 (2)	0.04453 (10)	0.0864 (2)	0.0245 (6)
H8A	0.8668	0.0341	0.0111	0.037*
H8B	0.7505	0.0289	0.0934	0.037*
H8C	0.8944	0.0296	0.1487	0.037*
C9	0.8305 (2)	0.10735 (10)	0.09594 (19)	0.0176 (5)
C10	0.7826 (2)	0.13304 (9)	0.19578 (19)	0.0173 (5)
C11	0.7760 (2)	0.19024 (9)	0.20381 (19)	0.0168 (5)
C12	0.7250 (2)	0.21978 (10)	0.3063 (2)	0.0202 (5)
H12A	0.6995	0.1920	0.3628	0.030*
H12B	0.6507	0.2425	0.2802	0.030*
H12C	0.7915	0.2441	0.3426	0.030*
C13	0.8209 (2)	0.22287 (9)	0.11100 (19)	0.0164 (5)
C14	0.8211 (2)	0.28242 (10)	0.1100 (2)	0.0204 (5)
H14	0.7912	0.3024	0.1740	0.024*
C15	0.8636 (2)	0.31132 (10)	0.0179 (2)	0.0221 (5)
H15	0.8635	0.3512	0.0185	0.027*
C16	0.9074 (2)	0.28255 (10)	−0.0774 (2)	0.0213 (5)
H16	0.9358	0.3030	−0.1415	0.026*
C17	0.9096 (2)	0.22560 (10)	−0.0792 (2)	0.0198 (5)
H17	0.9405	0.2067	−0.1441	0.024*
C18	0.8664 (2)	0.19410 (9)	0.01481 (19)	0.0162 (5)
C19	1.2324 (3)	0.06405 (10)	0.6756 (3)	0.0227 (8)	0.814 (2)
H19	1.3088	0.0523	0.6429	0.027*	0.814 (2)
C20	1.2283 (3)	0.08988 (9)	0.7808 (3)	0.0262 (8)	0.814 (2)
H20	1.3016	0.0983	0.8304	0.031*	0.814 (2)
C21	1.1044 (5)	0.10228 (15)	0.8064 (4)	0.0231 (12)	0.814 (2)
H21	1.0851	0.1205	0.8763	0.028*	0.814 (2)
C19'	1.2382 (12)	0.0828 (3)	0.7536 (10)	0.0227 (8)	0.186 (2)
H19B	1.3253	0.0851	0.7812	0.027*	0.186 (2)
C20'	1.1962 (11)	0.0594 (3)	0.6493 (9)	0.0262 (8)	0.186 (2)
H20B	1.2514	0.0437	0.5959	0.031*	0.186 (2)
C21'	1.0652 (12)	0.0613 (2)	0.6307 (7)	0.0231 (12)	0.186 (2)
H21B	1.0189	0.0473	0.5633	0.028*	0.186 (2)
C22	1.0104 (2)	0.08626 (9)	0.72294 (19)	0.0186 (5)
C23	0.8752 (2)	0.09631 (9)	0.7276 (2)	0.0172 (5)
H23	0.8484	0.1127	0.7970	0.021*
C24	0.7833 (2)	0.08503 (9)	0.6447 (2)	0.0185 (5)
H24	0.8061	0.0684	0.5742	0.022*
C25	0.6489 (2)	0.09748 (9)	0.6595 (2)	0.0184 (5)
C26	0.6714 (2)	0.22170 (10)	0.6441 (2)	0.0211 (5)
H26A	0.6954	0.1934	0.5880	0.032*
H26B	0.7465	0.2441	0.6692	0.032*
H26C	0.6054	0.2463	0.6078	0.032*
C27	0.6204 (2)	0.19306 (10)	0.74765 (19)	0.0173 (5)
C28	0.6142 (2)	0.13577 (9)	0.75760 (19)	0.0160 (5)
C29	0.5674 (2)	0.11100 (10)	0.85886 (19)	0.0176 (5)
C30	0.5630 (2)	0.04845 (9)	0.8706 (2)	0.0239 (6)
H30A	0.5345	0.0386	0.9471	0.036*
H30B	0.6484	0.0329	0.8623	0.036*
H30C	0.5033	0.0329	0.8101	0.036*
C31	0.5763 (2)	0.22622 (9)	0.84016 (19)	0.0161 (5)
C32	0.5758 (2)	0.28574 (10)	0.8390 (2)	0.0201 (5)
H32	0.6059	0.3052	0.7744	0.024*
C33	0.5327 (2)	0.31534 (10)	0.9295 (2)	0.0233 (6)
H33	0.5322	0.3552	0.9271	0.028*
C34	0.4888 (2)	0.28715 (10)	1.0269 (2)	0.0227 (6)
H34	0.4601	0.3081	1.0901	0.027*
C35	0.4877 (2)	0.22986 (10)	1.0305 (2)	0.0203 (5)
H35	0.4573	0.2112	1.0960	0.024*
C36	0.5314 (2)	0.19812 (9)	0.93734 (19)	0.0163 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0241 (5)	0.0243 (5)	0.0195 (5)	−0.0060 (4)	0.0075 (3)	−0.0004 (3)
S2	0.0227 (5)	0.0262 (5)	0.0201 (4)	0.0063 (3)	0.0063 (3)	−0.0009 (3)
S1'	0.0241 (5)	0.0243 (5)	0.0195 (5)	−0.0060 (4)	0.0075 (3)	−0.0004 (3)
S2'	0.0227 (5)	0.0262 (5)	0.0201 (4)	0.0063 (3)	0.0063 (3)	−0.0009 (3)
O1	0.0256 (10)	0.0285 (10)	0.0174 (9)	0.0003 (8)	−0.0019 (8)	0.0032 (7)
O2	0.0213 (9)	0.0341 (10)	0.0220 (9)	−0.0001 (8)	−0.0015 (8)	−0.0057 (8)
N1	0.0164 (10)	0.0207 (10)	0.0176 (10)	−0.0011 (8)	0.0014 (8)	−0.0021 (8)
N2	0.0173 (10)	0.0211 (10)	0.0160 (10)	0.0017 (8)	0.0027 (8)	0.0009 (8)
C1	0.0109 (15)	0.0289 (18)	0.034 (2)	−0.0063 (14)	0.0056 (16)	−0.0078 (16)
C2	0.0205 (18)	0.034 (2)	0.031 (2)	−0.0014 (15)	0.0037 (16)	0.0022 (16)
C3	0.023 (2)	0.035 (2)	0.018 (3)	−0.0026 (16)	−0.0002 (19)	0.0067 (18)
C1'	0.0109 (15)	0.0289 (18)	0.034 (2)	−0.0063 (14)	0.0056 (16)	−0.0078 (16)
C2'	0.0205 (18)	0.034 (2)	0.031 (2)	−0.0014 (15)	0.0037 (16)	0.0022 (16)
C3'	0.023 (2)	0.035 (2)	0.018 (3)	−0.0026 (16)	−0.0002 (19)	0.0067 (18)
C4	0.0207 (13)	0.0170 (12)	0.0211 (13)	−0.0017 (10)	0.0062 (10)	−0.0041 (10)
C5	0.0215 (13)	0.0170 (11)	0.0151 (11)	−0.0038 (10)	0.0071 (10)	−0.0024 (9)
C6	0.0235 (13)	0.0211 (12)	0.0168 (12)	−0.0040 (10)	0.0064 (10)	−0.0020 (10)
C7	0.0234 (13)	0.0170 (12)	0.0136 (11)	−0.0003 (10)	0.0034 (10)	−0.0026 (9)
C8	0.0302 (14)	0.0206 (13)	0.0234 (13)	−0.0020 (11)	0.0065 (11)	−0.0035 (10)
C9	0.0172 (12)	0.0215 (12)	0.0141 (11)	−0.0014 (10)	−0.0005 (10)	−0.0014 (9)
C10	0.0129 (12)	0.0242 (12)	0.0147 (11)	−0.0028 (10)	0.0008 (9)	0.0007 (9)
C11	0.0112 (11)	0.0236 (12)	0.0157 (11)	−0.0009 (10)	0.0003 (9)	−0.0030 (10)
C12	0.0203 (13)	0.0225 (12)	0.0183 (12)	0.0009 (10)	0.0053 (10)	−0.0037 (10)
C13	0.0114 (11)	0.0202 (12)	0.0173 (12)	0.0001 (9)	−0.0009 (9)	−0.0010 (9)
C14	0.0161 (12)	0.0215 (13)	0.0234 (13)	0.0018 (10)	0.0002 (10)	−0.0043 (10)
C15	0.0189 (13)	0.0192 (12)	0.0279 (14)	0.0017 (10)	−0.0009 (11)	0.0047 (10)
C16	0.0169 (13)	0.0269 (13)	0.0202 (13)	−0.0002 (10)	0.0016 (10)	0.0074 (10)
C17	0.0167 (12)	0.0260 (13)	0.0168 (12)	−0.0005 (10)	0.0030 (10)	0.0001 (10)
C18	0.0108 (11)	0.0218 (12)	0.0159 (12)	−0.0025 (10)	−0.0003 (9)	0.0000 (9)
C19	0.0129 (15)	0.0265 (17)	0.0296 (19)	0.0053 (13)	0.0086 (14)	0.0095 (14)
C20	0.0179 (16)	0.0256 (16)	0.035 (2)	0.0010 (13)	−0.0009 (15)	−0.0017 (14)
C21	0.024 (2)	0.0246 (19)	0.020 (2)	0.0005 (14)	−0.0058 (17)	−0.0020 (16)
C19'	0.0129 (15)	0.0265 (17)	0.0296 (19)	0.0053 (13)	0.0086 (14)	0.0095 (14)
C20'	0.0179 (16)	0.0256 (16)	0.035 (2)	0.0010 (13)	−0.0009 (15)	−0.0017 (14)
C21'	0.024 (2)	0.0246 (19)	0.020 (2)	0.0005 (14)	−0.0058 (17)	−0.0020 (16)
C22	0.0215 (13)	0.0156 (11)	0.0192 (12)	0.0012 (10)	0.0052 (10)	0.0023 (9)
C23	0.0202 (13)	0.0155 (11)	0.0164 (12)	−0.0013 (10)	0.0059 (10)	0.0014 (9)
C24	0.0197 (13)	0.0208 (12)	0.0154 (12)	0.0019 (10)	0.0038 (10)	0.0001 (10)
C25	0.0200 (13)	0.0197 (12)	0.0155 (12)	0.0002 (10)	0.0025 (10)	0.0031 (9)
C26	0.0209 (13)	0.0250 (13)	0.0179 (12)	−0.0004 (10)	0.0043 (10)	0.0030 (10)
C27	0.0119 (12)	0.0227 (12)	0.0171 (12)	−0.0015 (10)	−0.0001 (9)	0.0032 (10)
C28	0.0114 (11)	0.0228 (12)	0.0141 (11)	0.0039 (9)	0.0016 (9)	−0.0001 (9)
C29	0.0143 (12)	0.0218 (12)	0.0168 (12)	0.0016 (10)	0.0012 (9)	0.0023 (10)
C30	0.0313 (14)	0.0176 (12)	0.0232 (13)	0.0005 (11)	0.0064 (11)	0.0031 (10)
C31	0.0108 (11)	0.0196 (12)	0.0180 (12)	0.0007 (9)	0.0017 (9)	−0.0009 (9)
C32	0.0178 (13)	0.0209 (12)	0.0216 (13)	−0.0017 (10)	0.0013 (10)	0.0032 (10)
C33	0.0179 (13)	0.0189 (12)	0.0330 (15)	0.0002 (10)	0.0011 (11)	−0.0040 (11)
C34	0.0179 (13)	0.0265 (13)	0.0237 (13)	0.0011 (10)	0.0016 (10)	−0.0090 (11)
C35	0.0167 (12)	0.0250 (13)	0.0195 (13)	0.0024 (10)	0.0027 (10)	−0.0010 (10)
C36	0.0109 (11)	0.0218 (12)	0.0163 (12)	0.0010 (9)	0.0011 (9)	0.0003 (10)

Geometric parameters (Å, º) top

S1—C1	1.708 (3)	C14—H14	0.9500
S1—C4	1.721 (2)	C15—C16	1.399 (3)
S2—C22	1.717 (2)	C15—H15	0.9500
S2—C19	1.717 (3)	C16—C17	1.358 (3)
S1'—C4	1.646 (5)	C16—H16	0.9500
S1'—C1'	1.704 (8)	C17—C18	1.418 (3)
S2'—C22	1.649 (6)	C17—H17	0.9500
S2'—C19'	1.700 (8)	C19—C20	1.365 (4)
O1—C7	1.229 (3)	C19—H19	0.9500
O2—C25	1.227 (3)	C20—C21	1.384 (5)
N1—C9	1.319 (3)	C20—H20	0.9500
N1—C18	1.379 (3)	C21—C22	1.387 (4)
N2—C29	1.320 (3)	C21—H21	0.9500
N2—C36	1.370 (3)	C19'—C20'	1.374 (8)
C1—C2	1.362 (4)	C19'—H19B	0.9500
C1—H1	0.9500	C20'—C21'	1.379 (8)
C2—C3	1.379 (5)	C20'—H20B	0.9500
C2—H2	0.9500	C21'—C22	1.378 (7)
C3—C4	1.401 (5)	C21'—H21B	0.9500
C3—H3	0.9500	C22—C23	1.443 (3)
C1'—C2'	1.377 (8)	C23—C24	1.341 (3)
C1'—H1'	0.9500	C23—H23	0.9500
C2'—C3'	1.373 (8)	C24—C25	1.461 (3)
C2'—H2'	0.9500	C24—H24	0.9500
C3'—C4	1.369 (7)	C25—C28	1.517 (3)
C3'—H3'	0.9500	C26—C27	1.505 (3)
C4—C5	1.440 (3)	C26—H26A	0.9800
C5—C6	1.345 (3)	C26—H26B	0.9800
C5—H5	0.9500	C26—H26C	0.9800
C6—C7	1.465 (3)	C27—C28	1.373 (3)
C6—H6	0.9500	C27—C31	1.430 (3)
C7—C10	1.515 (3)	C28—C29	1.426 (3)
C8—C9	1.503 (3)	C29—C30	1.499 (3)
C8—H8A	0.9800	C30—H30A	0.9800
C8—H8B	0.9800	C30—H30B	0.9800
C8—H8C	0.9800	C30—H30C	0.9800
C9—C10	1.426 (3)	C31—C36	1.414 (3)
C10—C11	1.369 (3)	C31—C32	1.420 (3)
C11—C13	1.429 (3)	C32—C33	1.362 (3)
C11—C12	1.505 (3)	C32—H32	0.9500
C12—H12A	0.9800	C33—C34	1.413 (3)
C12—H12B	0.9800	C33—H33	0.9500
C12—H12C	0.9800	C34—C35	1.367 (3)
C13—C18	1.415 (3)	C34—H34	0.9500
C13—C14	1.420 (3)	C35—C36	1.416 (3)
C14—C15	1.367 (3)	C35—H35	0.9500

C1—S1—C4	92.77 (15)	N1—C18—C13	122.8 (2)
C22—S2—C19	92.72 (14)	N1—C18—C17	118.2 (2)
C4—S1'—C1'	90.5 (5)	C13—C18—C17	119.0 (2)
C22—S2'—C19'	91.3 (5)	C20—C19—S2	111.5 (2)
C9—N1—C18	117.9 (2)	C20—C19—H19	124.2
C29—N2—C36	118.1 (2)	S2—C19—H19	124.2
C2—C1—S1	112.5 (3)	C19—C20—C21	111.8 (3)
C2—C1—H1	123.7	C19—C20—H20	124.1
S1—C1—H1	123.7	C21—C20—H20	124.1
C1—C2—C3	110.9 (3)	C22—C21—C20	115.3 (4)
C1—C2—H2	124.5	C22—C21—H21	122.3
C3—C2—H2	124.5	C20—C21—H21	122.3
C2—C3—C4	116.1 (4)	C20'—C19'—S2'	111.5 (8)
C2—C3—H3	121.9	C20'—C19'—H19B	124.3
C4—C3—H3	121.9	S2'—C19'—H19B	124.3
C2'—C1'—S1'	111.3 (8)	C19'—C20'—C21'	112.5 (7)
C2'—C1'—H1'	124.3	C19'—C20'—H20B	123.8
S1'—C1'—H1'	124.3	C21'—C20'—H20B	123.8
C3'—C2'—C1'	112.8 (7)	C20'—C21'—C22	110.8 (6)
C3'—C2'—H2'	123.6	C20'—C21'—H21B	124.6
C1'—C2'—H2'	123.6	C22—C21'—H21B	124.6
C2'—C3'—C4	110.2 (6)	C21—C22—C21'	110.0 (6)
C2'—C3'—H3'	124.9	C21—C22—C23	125.8 (3)
C4—C3'—H3'	124.9	C21'—C22—C23	124.2 (6)
C3—C4—C3'	109.1 (6)	C21—C22—S2'	3.9 (4)
C3—C4—C5	125.9 (3)	C21'—C22—S2'	113.9 (5)
C3'—C4—C5	125.0 (5)	C23—C22—S2'	121.9 (3)
C3—C4—S1'	6.1 (4)	C21—C22—S2	108.6 (3)
C3'—C4—S1'	115.2 (5)	C21'—C22—S2	1.4 (5)
C5—C4—S1'	119.8 (3)	C23—C22—S2	125.55 (17)
C3—C4—S1	107.6 (3)	S2'—C22—S2	112.5 (3)
C3'—C4—S1	1.5 (5)	C24—C23—C22	127.1 (2)
C5—C4—S1	126.48 (17)	C24—C23—H23	116.5
S1'—C4—S1	113.7 (2)	C22—C23—H23	116.5
C6—C5—C4	126.9 (2)	C23—C24—C25	122.0 (2)
C6—C5—H5	116.6	C23—C24—H24	119.0
C4—C5—H5	116.6	C25—C24—H24	119.0
C5—C6—C7	121.5 (2)	O2—C25—C24	122.0 (2)
C5—C6—H6	119.3	O2—C25—C28	118.7 (2)
C7—C6—H6	119.3	C24—C25—C28	119.36 (19)
O1—C7—C6	121.6 (2)	C27—C26—H26A	109.5
O1—C7—C10	119.0 (2)	C27—C26—H26B	109.5
C6—C7—C10	119.41 (19)	H26A—C26—H26B	109.5
C9—C8—H8A	109.5	C27—C26—H26C	109.5
C9—C8—H8B	109.5	H26A—C26—H26C	109.5
H8A—C8—H8B	109.5	H26B—C26—H26C	109.5
C9—C8—H8C	109.5	C28—C27—C31	117.9 (2)
H8A—C8—H8C	109.5	C28—C27—C26	122.6 (2)
H8B—C8—H8C	109.5	C31—C27—C26	119.4 (2)
N1—C9—C10	122.9 (2)	C27—C28—C29	120.1 (2)
N1—C9—C8	116.8 (2)	C27—C28—C25	121.4 (2)
C10—C9—C8	120.3 (2)	C29—C28—C25	118.4 (2)
C11—C10—C9	120.3 (2)	N2—C29—C28	122.9 (2)
C11—C10—C7	120.9 (2)	N2—C29—C30	117.0 (2)
C9—C10—C7	118.7 (2)	C28—C29—C30	120.1 (2)
C10—C11—C13	118.1 (2)	C29—C30—H30A	109.5
C10—C11—C12	122.8 (2)	C29—C30—H30B	109.5
C13—C11—C12	119.1 (2)	H30A—C30—H30B	109.5
C11—C12—H12A	109.5	C29—C30—H30C	109.5
C11—C12—H12B	109.5	H30A—C30—H30C	109.5
H12A—C12—H12B	109.5	H30B—C30—H30C	109.5
C11—C12—H12C	109.5	C36—C31—C32	118.7 (2)
H12A—C12—H12C	109.5	C36—C31—C27	118.2 (2)
H12B—C12—H12C	109.5	C32—C31—C27	123.2 (2)
C18—C13—C14	118.5 (2)	C33—C32—C31	120.8 (2)
C18—C13—C11	118.0 (2)	C33—C32—H32	119.6
C14—C13—C11	123.5 (2)	C31—C32—H32	119.6
C15—C14—C13	120.7 (2)	C32—C33—C34	120.4 (2)
C15—C14—H14	119.6	C32—C33—H33	119.8
C13—C14—H14	119.6	C34—C33—H33	119.8
C14—C15—C16	120.4 (2)	C35—C34—C33	120.3 (2)
C14—C15—H15	119.8	C35—C34—H34	119.9
C16—C15—H15	119.8	C33—C34—H34	119.9
C17—C16—C15	120.6 (2)	C34—C35—C36	120.5 (2)
C17—C16—H16	119.7	C34—C35—H35	119.8
C15—C16—H16	119.7	C36—C35—H35	119.8
C16—C17—C18	120.8 (2)	N2—C36—C31	122.8 (2)
C16—C17—H17	119.6	N2—C36—C35	117.8 (2)
C18—C17—H17	119.6	C31—C36—C35	119.4 (2)

C4—S1—C1—C2	−0.36 (11)	C22—S2—C19—C20	−0.20 (10)
S1—C1—C2—C3	−0.33 (19)	S2—C19—C20—C21	−0.04 (19)
C1—C2—C3—C4	1.1 (3)	C19—C20—C21—C22	0.3 (3)
C4—S1'—C1'—C2'	1.0 (4)	C22—S2'—C19'—C20'	0.5 (4)
S1'—C1'—C2'—C3'	−0.7 (6)	S2'—C19'—C20'—C21'	−0.2 (6)
C1'—C2'—C3'—C4	−0.2 (6)	C19'—C20'—C21'—C22	−0.3 (6)
C2—C3—C4—C3'	−1.4 (4)	C20—C21—C22—C21'	−0.5 (4)
C2—C3—C4—C5	179.2 (2)	C20—C21—C22—C23	−177.6 (2)
C2—C3—C4—S1	−1.3 (3)	C20—C21—C22—S2	−0.5 (3)
C2'—C3'—C4—C3	0.9 (5)	C20'—C21'—C22—C21	0.4 (5)
C2'—C3'—C4—C5	−179.6 (3)	C20'—C21'—C22—C23	177.6 (3)
C2'—C3'—C4—S1'	1.0 (5)	C20'—C21'—C22—S2'	0.6 (5)
C2'—C3'—C4—S1	−1 (8)	C20'—C21'—C22—S2	−1 (8)
C1'—S1'—C4—C3	−1 (2)	C19'—S2'—C22—C21	2 (4)
C1'—S1'—C4—C3'	−1.2 (4)	C19'—S2'—C22—C21'	−0.6 (4)
C1'—S1'—C4—C5	179.4 (2)	C19'—S2'—C22—C23	−177.7 (2)
C1'—S1'—C4—S1	−1.1 (3)	C19'—S2'—C22—S2	−0.6 (3)
C1—S1—C4—C3	0.9 (2)	C19—S2—C22—C21	0.38 (19)
C1—S1—C4—C5	−179.6 (2)	C19—S2—C22—C23	177.5 (2)
C1—S1—C4—S1'	0.96 (18)	C19—S2—C22—S2'	0.55 (19)
C3—C4—C5—C6	−177.5 (3)	C21—C22—C23—C24	174.7 (3)
C3'—C4—C5—C6	3.1 (4)	C21'—C22—C23—C24	−2.0 (4)
S1'—C4—C5—C6	−177.5 (2)	S2'—C22—C23—C24	174.8 (2)
S1—C4—C5—C6	3.1 (4)	S2—C22—C23—C24	−2.0 (3)
C4—C5—C6—C7	179.7 (2)	C22—C23—C24—C25	−179.7 (2)
C5—C6—C7—O1	−169.4 (2)	C23—C24—C25—O2	−165.9 (2)
C5—C6—C7—C10	11.5 (3)	C23—C24—C25—C28	14.3 (3)
C18—N1—C9—C10	0.1 (3)	C31—C27—C28—C29	−1.2 (3)
C18—N1—C9—C8	179.80 (19)	C26—C27—C28—C29	178.7 (2)
N1—C9—C10—C11	0.5 (3)	C31—C27—C28—C25	175.06 (19)
C8—C9—C10—C11	−179.1 (2)	C26—C27—C28—C25	−5.0 (3)
N1—C9—C10—C7	−176.5 (2)	O2—C25—C28—C27	−98.7 (3)
C8—C9—C10—C7	3.9 (3)	C24—C25—C28—C27	81.1 (3)
O1—C7—C10—C11	−98.3 (3)	O2—C25—C28—C29	77.7 (3)
C6—C7—C10—C11	80.8 (3)	C24—C25—C28—C29	−102.5 (3)
O1—C7—C10—C9	78.7 (3)	C36—N2—C29—C28	0.4 (3)
C6—C7—C10—C9	−102.2 (3)	C36—N2—C29—C30	179.72 (19)
C9—C10—C11—C13	−1.4 (3)	C27—C28—C29—N2	0.4 (3)
C7—C10—C11—C13	175.53 (19)	C25—C28—C29—N2	−176.0 (2)
C9—C10—C11—C12	179.3 (2)	C27—C28—C29—C30	−178.8 (2)
C7—C10—C11—C12	−3.8 (3)	C25—C28—C29—C30	4.7 (3)
C10—C11—C13—C18	1.7 (3)	C28—C27—C31—C36	1.2 (3)
C12—C11—C13—C18	−178.99 (19)	C26—C27—C31—C36	−178.75 (19)
C10—C11—C13—C14	−178.9 (2)	C28—C27—C31—C32	−178.9 (2)
C12—C11—C13—C14	0.4 (3)	C26—C27—C31—C32	1.2 (3)
C18—C13—C14—C15	0.3 (3)	C36—C31—C32—C33	−0.1 (3)
C11—C13—C14—C15	−179.1 (2)	C27—C31—C32—C33	180.0 (2)
C13—C14—C15—C16	0.3 (3)	C31—C32—C33—C34	0.6 (3)
C14—C15—C16—C17	−0.8 (3)	C32—C33—C34—C35	−0.9 (3)
C15—C16—C17—C18	0.7 (3)	C33—C34—C35—C36	0.6 (3)
C9—N1—C18—C13	0.2 (3)	C29—N2—C36—C31	−0.4 (3)
C9—N1—C18—C17	−179.94 (19)	C29—N2—C36—C35	179.47 (19)
C14—C13—C18—N1	179.5 (2)	C32—C31—C36—N2	179.7 (2)
C11—C13—C18—N1	−1.1 (3)	C27—C31—C36—N2	−0.4 (3)
C14—C13—C18—C17	−0.4 (3)	C32—C31—C36—C35	−0.2 (3)
C11—C13—C18—C17	179.03 (19)	C27—C31—C36—C35	179.71 (19)
C16—C17—C18—N1	−180.0 (2)	C34—C35—C36—N2	−179.9 (2)
C16—C17—C18—C13	−0.1 (3)	C34—C35—C36—C31	0.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C31–C36 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2ⁱ	0.95	2.51	3.391 (3)	154
C6—H6···O2	0.95	2.55	3.382 (3)	146
C23—H23···N1ⁱⁱ	0.95	2.50	3.382 (3)	154
C24—H24···O1	0.95	2.48	3.330 (3)	149
C12—H12c···Cg1ⁱⁱⁱ	0.98	2.67	142	4 (1)
C26—H26c···Cg2^iv	0.98	2.67	143	4 (1)

Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1; (iii) x−1/2, −y−1/2, z−3/2; (iv) x−3/2, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅NOS
M_r	293.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.4935 (4), 23.8464 (8), 11.5464 (4)
β (°)	93.756 (3)
V (Å³)	2883.07 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.947, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	14916, 6427, 4075
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.160, 1.03
No. of reflections	6427
No. of parameters	409
No. of restraints	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.46

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C31–C36 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2ⁱ	0.95	2.51	3.391 (3)	154
C6—H6···O2	0.95	2.55	3.382 (3)	146
C23—H23···N1ⁱⁱ	0.95	2.50	3.382 (3)	154
C24—H24···O1	0.95	2.48	3.330 (3)	149
C12—H12c···Cg1ⁱⁱⁱ	0.98	2.67	142	3.499 (2)
C26—H26c···Cg2^iv	0.98	2.67	143	3.503 (2)

Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1; (iii) x−1/2, −y−1/2, z−3/2; (iv) x−3/2, −y−1/2, z−1/2.

Footnotes

†Additional correspondence author, e-mail: juliebhavana@yahoo.co.in.

Acknowledgements

PB acknowledges the Department of Science and Technology (DST), India, for a research grant (SR/FTP/CS-57/2007). The authors also thank the University of Malaya for support of the crystallographic facility.

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Volume 67| Part 9| September 2011| Pages o2283-o2284

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