tert-Butyl 2-{[5-(4-cyano­phen­yl)pyridin-3-yl]sulfon­yl}acetate

Devarajegowda, H.C.; Palakshamurthy, B.S.; Manojkumar, K.E.; Sreenivasa, S.

doi:10.1107/S160053681400511X

organic compounds

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Volume 70| Part 4| April 2014| Page o415

doi:10.1107/S160053681400511X

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tert-Butyl 2-{[5-(4-cyanophenyl)pyridin-3-yl]sulfonyl}acetate

H. C. Devarajegowda,^a B. S. Palakshamurthy,^a ^* K. E. Manojkumar ^b and S. Sreenivasa ^b

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Karnataka, India, and ^bDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: palaksha.bspm@gmail.com

(Received 26 February 2014; accepted 6 March 2014; online 12 March 2014)

In the title compound, C₁₈H₁₈N₂O₄S, the dihedral angle between the aromatic rings is 33.71 (9)° and an intramolecular C—H⋯O hydrogen bond closes an S(6) ring. In the crystal, molecules are linked by C—H⋯O and C—H⋯N hydrogen bonds to generate a three-dimensional network. A very weak aromatic π–π stacking interction is also observed [centroid–centroid separation = 3.9524 (10) Å].

CCDC reference: 985495

Related literature

For the biological activity of nitrogen-containing heterocylces, see: Demirbas et al. (2005 ); Manojkumar et al. (2013 ).

Experimental

Crystal data

C₁₈H₁₈N₂O₄S
M_r = 358.40
Monoclinic, P 2₁ /c
a = 17.3871 (7) Å
b = 12.5318 (5) Å
c = 8.4297 (3) Å
β = 99.103 (2)°
V = 1813.63 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 294 K
0.36 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.931, T_max = 0.957
13884 measured reflections
3176 independent reflections
2649 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.113
S = 1.07
3176 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1ⁱ	0.93	2.50	3.210 (2)	134
C12—H12⋯N2ⁱⁱ	0.93	2.60	3.518 (2)	172
C13—H13A⋯O1ⁱⁱⁱ	0.97	2.54	3.347 (2)	141
C16—H16A⋯O4	0.96	2.36	2.971 (4)	121
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; 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: SHELXL97.

Supporting information

CCDC reference: 985495

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053681400511X/hb7202sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681400511X/hb7202Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681400511X/hb7202Isup3.cml

checkCIF report

Comment top

Nitrogen containing heterocyclic molecules show properties like Antibacterial, Anthelmintic and Anti-Inflammatory Agents antifungal [Manojkumar et al., 2013; Demirbas et al., 2005] etc. In perticular, 4-pyridin-3-yl benzonitrile nucleus has been the focus of our recent research related to design liquid crystals (our unpublished results). Keeping this in mind the title compound was synthesized and its crystal structure determined.

In the title structure, C₁₈H₁₈N₂O₄S, the dihedral angle between benzene and pyridine ring is 33.71 (9)°. and an intramolecular C16—H16A···O4 hydrogen bond closes an S(6) ring. The crystal structure displays C9—H9···O1, C13—H13A···O1 and C12—H12···N2 hydrogen bonding forming C(7), C(4) and C(5) chains along [010], [001] and [010] respectively. A weak aromatic π-π stacking interaction is also observed [centroid-centroid separation = 3.9524 (10) Å].

Related literature top

For the biological activity of nitrogen-containing heterocylces, see: Mathew et al. (2007); Demirbas et al. (2005); Manojkumar et al. (2013).

Experimental top

5-(Methylsulfonyl)pyridin-3-ylboronic acid (1 mol) was taken in 1,4-dioxane and water (60:40 ml). Bis(triphenylphosphine)palladium(II) dichloride (dikis) (0.03 mol) and K₂CO₃ (3 mol) were added to the above solution. The solvent was degassed with argon for one hour and 4-iodobenzonitrile (1 mol) was added. Heated the contents for 5 h. The reaction was monitored by TLC, filtered the reaction mixture by using celite and the solvent was removed by rota evaporator. The crude compound was purified by 60–120 silica gel column chromatography to yield pure yellow solid of 4-(5-(methylsulfonyl)pyridin-3-yl)benzonitrile.

4-(5-(methylsulfonyl)pyridin-3-yl)benzonitrile (1 mol) was taken in dry THF (25 ml) and to this Lithium Hexamethyldisilazide (LiHMDS) in THF (1.5 mol) and Boc anhydride were added. The. reaction mixture was stirred at room temperature for 5 h and completion of the reaction was confirmed by TLC. The reaction mixture was quenched by ice cold water and later extracted with ethyl acetate. Solvent was dried over anhydrous sodium sulfate and concentrated under vacuum to give crude product. The crude Product obtained was purified by column chromatography to get pure tert-butyl 2-(5-(4-cyanophenyl)pyridin-3-ylsulfonyl)acetate, which was recrystallized by dichloromethane and methanol (9:1) system to yield colourless prisms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker,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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing of the molecule.
	Fig. 3. The molecule with π-π stacking.

tert-Butyl 2-{[5-(4-cyanophenyl)pyridin-3-yl]sulfonyl}acetate top

Crystal data top

C₁₈H₁₈N₂O₄S	F(000) = 752
M_r = 358.40	Prism
Monoclinic, P2₁/c	D_x = 1.313 Mg m⁻³
Hall symbol: -P 2ybc	Melting point: 423 K
a = 17.3871 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.5318 (5) Å	θ = 0–25°
c = 8.4297 (3) Å	µ = 0.20 mm⁻¹
β = 99.103 (2)°	T = 294 K
V = 1813.63 (12) Å³	Prism, colourless
Z = 4	0.36 × 0.28 × 0.22 mm

Data collection top

Bruker APEXII CCD diffractometer	3176 independent reflections
Radiation source: fine-focus sealed tube	2649 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 1.6 pixels mm^-1	θ_max = 25.0°, θ_min = 1.2°
ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
T_min = 0.931, T_max = 0.957	l = −10→9
13884 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0589P)² + 0.3788P] where P = (F_o² + 2F_c²)/3
3176 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³
0 constraints

Crystal data top

C₁₈H₁₈N₂O₄S	V = 1813.63 (12) Å³
M_r = 358.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.3871 (7) Å	µ = 0.20 mm⁻¹
b = 12.5318 (5) Å	T = 294 K
c = 8.4297 (3) Å	0.36 × 0.28 × 0.22 mm
β = 99.103 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3176 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2649 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.957	R_int = 0.029
13884 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.07	Δρ_max = 0.23 e Å⁻³
3176 reflections	Δρ_min = −0.30 e Å⁻³
229 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C7	−0.33192 (14)	0.7433 (2)	0.5018 (3)	0.0863 (7)
C16	0.44601 (18)	0.7075 (4)	0.2350 (6)	0.170 (2)
H16A	0.4171	0.7677	0.1870	0.254*
H16B	0.4942	0.7020	0.1936	0.254*
H16C	0.4567	0.7168	0.3494	0.254*
C18	0.4351 (2)	0.5073 (5)	0.2805 (5)	0.183 (2)
H18A	0.4449	0.5197	0.3943	0.274*
H18B	0.4833	0.4916	0.2435	0.274*
H18C	0.4001	0.4481	0.2575	0.274*
C13	0.19857 (10)	0.66538 (18)	0.2825 (2)	0.0598 (5)
H13A	0.1805	0.7282	0.3330	0.072*
H13B	0.2073	0.6087	0.3617	0.072*
N1	−0.38426 (14)	0.7818 (2)	0.5450 (4)	0.1214 (9)
C1	−0.13164 (10)	0.70509 (14)	0.4150 (2)	0.0508 (4)
H1	−0.0852	0.7431	0.4249	0.061*
C2	−0.19560 (11)	0.75155 (16)	0.4633 (2)	0.0587 (5)
H2	−0.1925	0.8205	0.5048	0.070*
C3	−0.26510 (11)	0.69460 (18)	0.4497 (3)	0.0650 (5)
C4	−0.26913 (12)	0.5924 (2)	0.3865 (3)	0.0738 (6)
H4	−0.3155	0.5543	0.3773	0.089*
C5	−0.20474 (11)	0.54709 (16)	0.3371 (3)	0.0618 (5)
H5	−0.2081	0.4787	0.2937	0.074*
C6	−0.13473 (10)	0.60278 (14)	0.3517 (2)	0.0465 (4)
C8	−0.06428 (10)	0.55338 (13)	0.3044 (2)	0.0448 (4)
C9	−0.05133 (11)	0.44394 (14)	0.3242 (2)	0.0540 (5)
H9	−0.0891	0.4041	0.3644	0.065*
C10	0.06362 (11)	0.45021 (15)	0.2309 (2)	0.0573 (5)
H10	0.1078	0.4160	0.2065	0.069*
C11	0.05613 (10)	0.55892 (13)	0.2040 (2)	0.0465 (4)
C12	−0.00844 (9)	0.61241 (13)	0.24214 (19)	0.0438 (4)
H12	−0.0141	0.6856	0.2264	0.053*
C14	0.27308 (11)	0.6900 (2)	0.2182 (3)	0.0650 (5)
C15	0.39872 (15)	0.6065 (3)	0.1954 (3)	0.1037 (10)
C17	0.37939 (19)	0.5867 (3)	0.0188 (4)	0.1206 (12)
H17A	0.3463	0.5252	−0.0002	0.181*
H17B	0.4265	0.5743	−0.0244	0.181*
H17C	0.3530	0.6477	−0.0326	0.181*
N2	0.01068 (10)	0.39231 (12)	0.2900 (2)	0.0609 (4)
O4	0.27975 (10)	0.76620 (15)	0.1362 (2)	0.0938 (5)
O3	0.32424 (8)	0.61363 (14)	0.26226 (18)	0.0771 (5)
O1	0.09398 (8)	0.71741 (11)	0.03461 (16)	0.0627 (4)
O2	0.16443 (8)	0.54780 (12)	0.02716 (17)	0.0701 (4)
S1	0.12816 (2)	0.62493 (4)	0.11611 (5)	0.04867 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C7	0.0629 (14)	0.1074 (19)	0.0937 (18)	−0.0008 (13)	0.0278 (13)	−0.0104 (15)
C16	0.0595 (17)	0.286 (6)	0.172 (4)	−0.048 (3)	0.044 (2)	−0.076 (4)
C18	0.125 (3)	0.295 (6)	0.133 (3)	0.124 (4)	0.034 (2)	0.053 (4)
C13	0.0522 (10)	0.0798 (13)	0.0471 (10)	−0.0020 (10)	0.0066 (8)	−0.0097 (10)
N1	0.0791 (15)	0.152 (2)	0.143 (2)	0.0081 (15)	0.0480 (16)	−0.0270 (19)
C1	0.0500 (10)	0.0471 (9)	0.0554 (11)	−0.0024 (8)	0.0084 (8)	0.0019 (8)
C2	0.0620 (12)	0.0573 (11)	0.0580 (11)	0.0028 (9)	0.0136 (9)	−0.0043 (9)
C3	0.0557 (11)	0.0787 (14)	0.0633 (12)	0.0010 (10)	0.0175 (9)	−0.0019 (11)
C4	0.0544 (12)	0.0871 (15)	0.0825 (15)	−0.0177 (11)	0.0185 (11)	−0.0093 (13)
C5	0.0583 (11)	0.0599 (11)	0.0679 (13)	−0.0118 (9)	0.0123 (10)	−0.0093 (10)
C6	0.0498 (10)	0.0466 (9)	0.0422 (9)	−0.0035 (7)	0.0048 (7)	0.0039 (7)
C8	0.0494 (9)	0.0417 (9)	0.0404 (9)	−0.0025 (7)	−0.0022 (7)	−0.0024 (7)
C9	0.0607 (11)	0.0433 (9)	0.0548 (11)	−0.0050 (8)	−0.0009 (9)	−0.0002 (8)
C10	0.0588 (11)	0.0461 (10)	0.0645 (12)	0.0088 (8)	0.0021 (9)	−0.0083 (9)
C11	0.0489 (9)	0.0438 (9)	0.0450 (9)	0.0031 (7)	0.0016 (7)	−0.0060 (7)
C12	0.0504 (9)	0.0367 (8)	0.0428 (9)	0.0014 (7)	0.0030 (7)	−0.0020 (7)
C14	0.0531 (11)	0.0853 (15)	0.0557 (12)	−0.0063 (11)	0.0060 (9)	−0.0034 (11)
C15	0.0592 (14)	0.178 (3)	0.0767 (17)	0.0234 (17)	0.0182 (13)	−0.0039 (18)
C17	0.111 (2)	0.173 (3)	0.085 (2)	0.028 (2)	0.0357 (18)	−0.008 (2)
N2	0.0655 (10)	0.0415 (8)	0.0720 (11)	0.0035 (7)	−0.0003 (9)	−0.0032 (7)
O4	0.0804 (11)	0.0995 (13)	0.1034 (14)	−0.0137 (9)	0.0205 (10)	0.0215 (11)
O3	0.0532 (8)	0.1156 (13)	0.0628 (9)	0.0117 (8)	0.0100 (7)	0.0074 (8)
O1	0.0598 (8)	0.0680 (8)	0.0619 (8)	0.0062 (6)	0.0144 (6)	0.0128 (7)
O2	0.0682 (9)	0.0816 (10)	0.0631 (8)	0.0095 (7)	0.0183 (7)	−0.0248 (7)
S1	0.0487 (3)	0.0559 (3)	0.0418 (3)	0.00573 (19)	0.00817 (18)	−0.00699 (19)

Geometric parameters (Å, º) top

C7—N1	1.139 (3)	C5—H5	0.9300
C7—C3	1.441 (3)	C6—C8	1.482 (2)
C16—C15	1.518 (5)	C8—C12	1.388 (2)
C16—H16A	0.9600	C8—C9	1.396 (2)
C16—H16B	0.9600	C9—N2	1.327 (2)
C16—H16C	0.9600	C9—H9	0.9300
C18—C15	1.521 (5)	C10—N2	1.329 (2)
C18—H18A	0.9600	C10—C11	1.384 (3)
C18—H18B	0.9600	C10—H10	0.9300
C18—H18C	0.9600	C11—C12	1.388 (2)
C13—C14	1.513 (3)	C11—S1	1.7595 (18)
C13—S1	1.7830 (18)	C12—H12	0.9300
C13—H13A	0.9700	C14—O4	1.195 (3)
C13—H13B	0.9700	C14—O4	1.195 (3)
C1—C2	1.373 (3)	C14—O4	1.195 (3)
C1—C6	1.386 (2)	C14—O3	1.320 (3)
C1—H1	0.9300	C15—O3	1.494 (3)
C2—C3	1.392 (3)	C15—C17	1.495 (4)
C2—H2	0.9300	C17—H17A	0.9600
C3—C4	1.385 (3)	C17—H17B	0.9600
C4—C5	1.377 (3)	C17—H17C	0.9600
C4—H4	0.9300	O1—S1	1.4280 (14)
C5—C6	1.392 (2)	O2—S1	1.4297 (13)

N1—C7—C3	179.1 (3)	N2—C9—C8	125.05 (18)
C15—C16—H16A	109.5	N2—C9—H9	117.5
C15—C16—H16B	109.5	C8—C9—H9	117.5
H16A—C16—H16B	109.5	N2—C10—C11	123.10 (17)
C15—C16—H16C	109.5	N2—C10—H10	118.5
H16A—C16—H16C	109.5	C11—C10—H10	118.5
H16B—C16—H16C	109.5	C10—C11—C12	119.73 (17)
C15—C18—H18A	109.5	C10—C11—S1	118.50 (14)
C15—C18—H18B	109.5	C12—C11—S1	121.74 (13)
H18A—C18—H18B	109.5	C8—C12—C11	118.02 (15)
C15—C18—H18C	109.5	C8—C12—H12	121.0
H18A—C18—H18C	109.5	C11—C12—H12	121.0
H18B—C18—H18C	109.5	O4—C14—O3	128.3 (2)
C14—C13—S1	107.26 (13)	O4—C14—O3	128.3 (2)
C14—C13—H13A	110.3	O4—C14—O3	128.3 (2)
S1—C13—H13A	110.3	O4—C14—C13	122.5 (2)
C14—C13—H13B	110.3	O4—C14—C13	122.5 (2)
S1—C13—H13B	110.3	O4—C14—C13	122.5 (2)
H13A—C13—H13B	108.5	O3—C14—C13	109.17 (19)
C2—C1—C6	121.49 (17)	O3—C15—C17	108.3 (2)
C2—C1—H1	119.3	O3—C15—C16	109.8 (2)
C6—C1—H1	119.3	C17—C15—C16	112.7 (3)
C1—C2—C3	119.43 (19)	O3—C15—C18	101.1 (3)
C1—C2—H2	120.3	C17—C15—C18	110.2 (3)
C3—C2—H2	120.3	C16—C15—C18	114.0 (3)
C4—C3—C2	119.74 (19)	C15—C17—H17A	109.5
C4—C3—C7	121.0 (2)	C15—C17—H17B	109.5
C2—C3—C7	119.3 (2)	H17A—C17—H17B	109.5
C5—C4—C3	120.25 (19)	C15—C17—H17C	109.5
C5—C4—H4	119.9	H17A—C17—H17C	109.5
C3—C4—H4	119.9	H17B—C17—H17C	109.5
C4—C5—C6	120.53 (19)	C9—N2—C10	116.72 (16)
C4—C5—H5	119.7	C14—O3—C15	121.6 (2)
C6—C5—H5	119.7	O1—S1—O2	118.74 (9)
C1—C6—C5	118.55 (17)	O1—S1—C11	108.33 (8)
C1—C6—C8	120.42 (15)	O2—S1—C11	107.78 (9)
C5—C6—C8	121.01 (16)	O1—S1—C13	109.23 (10)
C12—C8—C9	117.37 (16)	O2—S1—C13	107.45 (9)
C12—C8—C6	122.44 (15)	C11—S1—C13	104.38 (9)
C9—C8—C6	120.19 (16)

C6—C1—C2—C3	0.4 (3)	S1—C13—C14—O3	−107.14 (17)
C1—C2—C3—C4	−0.6 (3)	C8—C9—N2—C10	−0.7 (3)
C1—C2—C3—C7	179.5 (2)	C11—C10—N2—C9	−0.4 (3)
C2—C3—C4—C5	0.0 (3)	O4—C14—O4—O4	0.0 (4)
C7—C3—C4—C5	179.9 (2)	O3—C14—O4—O4	0.0 (4)
C3—C4—C5—C6	0.7 (3)	C13—C14—O4—O4	0.0 (3)
C2—C1—C6—C5	0.2 (3)	O4—C14—O4—O4	0.0 (4)
C2—C1—C6—C8	−178.38 (17)	O3—C14—O4—O4	0.0 (4)
C4—C5—C6—C1	−0.8 (3)	C13—C14—O4—O4	0.0 (3)
C4—C5—C6—C8	177.81 (19)	O4—C14—O3—C15	−7.3 (4)
C1—C6—C8—C12	−33.7 (2)	O4—C14—O3—C15	−7.3 (4)
C5—C6—C8—C12	147.77 (18)	O4—C14—O3—C15	−7.3 (4)
C1—C6—C8—C9	145.27 (18)	C13—C14—O3—C15	170.12 (19)
C5—C6—C8—C9	−33.3 (2)	C17—C15—O3—C14	−63.6 (4)
C12—C8—C9—N2	0.9 (3)	C16—C15—O3—C14	59.8 (3)
C6—C8—C9—N2	−178.05 (16)	C18—C15—O3—C14	−179.4 (3)
N2—C10—C11—C12	1.2 (3)	C10—C11—S1—O1	153.88 (15)
N2—C10—C11—S1	−176.94 (15)	C12—C11—S1—O1	−24.24 (16)
C9—C8—C12—C11	0.0 (2)	C10—C11—S1—O2	24.22 (17)
C6—C8—C12—C11	178.94 (15)	C12—C11—S1—O2	−153.90 (14)
C10—C11—C12—C8	−1.0 (2)	C10—C11—S1—C13	−89.82 (16)
S1—C11—C12—C8	177.12 (12)	C12—C11—S1—C13	92.06 (15)
S1—C13—C14—O4	70.4 (3)	C14—C13—S1—O1	−82.29 (16)
S1—C13—C14—O4	70.4 (3)	C14—C13—S1—O2	47.76 (18)
S1—C13—C14—O4	70.4 (3)	C14—C13—S1—C11	162.04 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.93	2.50	3.210 (2)	134
C12—H12···N2ⁱⁱ	0.93	2.60	3.518 (2)	172
C13—H13A···O1ⁱⁱⁱ	0.97	2.54	3.347 (2)	141
C16—H16A···O4	0.96	2.36	2.971 (4)	121

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.93	2.50	3.210 (2)	134
C12—H12···N2ⁱⁱ	0.93	2.60	3.518 (2)	172
C13—H13A···O1ⁱⁱⁱ	0.97	2.54	3.347 (2)	141
C16—H16A···O4	0.96	2.36	2.971 (4)	121

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

Acknowledgements

The authors thank H. T. Srinivasa, Raman Research Institute, Bangalore, India, and Dr P. A. Suchethan, University College of Science, Tumkur, India, for useful discussions.

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