8,13,26-Trioxa-23-thia-21-aza­penta­cyclo­[18.6.0.02,7.014,19.021,25]hexa­cosa-2(7),3,5,14,16,18-hexa­ene

Devi, S.K.; Srinivasan, T.; Purushothaman, S.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536813012804

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o892

doi:10.1107/S1600536813012804

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8,13,26-Trioxa-23-thia-21-azapentacyclo[18.6.0.0^2,7.0^14,19.0^21,25]hexacosa-2(7),3,5,14,16,18-hexaene

Seenivasan Karthiga Devi,^a Thothadri Srinivasan,^a Santhanagopalan Purushothaman,^b Raghavachary Raghunathan ^b and Devadasan Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 2 May 2013; accepted 9 May 2013; online 15 May 2013)

In the title compound, C₂₁H₂₃NO₃S, both the thiazole and oxazolidine rings adopt twist conformations. The mean plane of the thiazole ring makes a dihedral angle of 61.02 (7)° with the oxazolidine ring mean plane, and dihedral angles of 22.72 (6) and 75.07 (6)° with the benzene rings. The benzene rings are almost perpendicular to one another, making a dihedral angle of 89.14 (6)°. There are bifurcated intramolecular C—H⋯O hydrogen bonds in the molecular structure. In the crystal, molecules are linked via C—H⋯π interactions, forming chains propagating along [100].

Related literature

For the biological activity of thiazole derivatives, see: Guo et al. (2006 ); Karegoudar et al. (2008 ); Reddy et al. (1999 ).

Experimental

Crystal data

C₂₁H₂₃NO₃S
M_r = 369.46
Monoclinic, P 2₁ /c
a = 9.9858 (5) Å
b = 17.8830 (8) Å
c = 10.2054 (4) Å
β = 94.663 (2)°
V = 1816.41 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.943, T_max = 0.961
29183 measured reflections
7768 independent reflections
5150 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.152
S = 1.02
7768 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.98	2.30	2.9593 (13)	123
C8—H8⋯O2	0.98	2.30	2.7146 (14)	104
C3—H3⋯Cg1ⁱ	0.93	2.99	3.8672 (14)	158
C16—H16B⋯Cg1ⁱⁱ	0.97	2.81	3.7400 (17)	160
Symmetry codes: (i) x-1, y, z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813012804/su2596sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012804/su2596Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813012804/su2596Isup3.cml

checkCIF report

Comment top

Thiazole derivatives have a variety of physiological effects, such as antiinflammatory (Guo et al., 2006) and antimicrobial (Karegoudar et al., 2008). Against this background, we report herein on the crystal structure of the title thiazole derivative.

In the title compound, Fig. 1, both the thiazole ring (S1/N1/C19-C21) and the oxazolidine ring (O3/N1/C7/C8/C19) adopt twist conformations. The former is twisted on bond S1-C21, while the latter is twisted on bond C8-C7. Their mean planes are inclined to one another by 61.02 (7)°. The mean plane of the thiazole ring makes a dihedral angle of 22.72 (6)° with benzene ring (C1-C6), and a dihedral angle of 75.07 (6)° with the other benzene ring (C9-C14). The dihedral angle between the two benzene rings is 89.14 (6)°. The oxazolidine ring mean plane makes dihedral angles of 81.69 (6)° with benzene ring (C1-C6) and 68.92 (6)° with benzene ring (C9-C14).

The molecule features bifurcated intramolecular C–H···O hydrogen bonds (Table 1).

In the crystal, molecules are linked via C-H···π interactions forming chains along direction [100]; see Table 1.

Related literature top

For the biological activity of thiazole derivatives, see: Guo et al. (2006); Karegoudar et al. (2008); Reddy et al. (1999).

Experimental top

A mixture of 2,2'-(butane-1,4-diylbis(oxy))dibenzaldehyde (1 mMol) and thiazolidine-4-carboxylic acid (1 mMol) was refluxed in acetonitrile (30 ml) for about 6 hrs under N₂ atm. After the completion of reaction as indicated by TLC, acetonitrile was evaporated under reduced pressure. The crude product was purified by column chromatography using hexane: EtOAc (8:2) mixture as eluent. Block-like colourless crystals of the title compound, suitable for X-ray diffraction, were obtained by slow evaporation of a solution in ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

8,13,26-Trioxa-23-thia-21-azapentacyclo[18.6.0.0^2,7.0^14,19.0^21,25]hexacosa-2(7),3,5,14,16,18-hexaene top

Crystal data top

C₂₁H₂₃NO₃S	F(000) = 784
M_r = 369.46	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7768 reflections
a = 9.9858 (5) Å	θ = 2.1–34.8°
b = 17.8830 (8) Å	µ = 0.20 mm⁻¹
c = 10.2054 (4) Å	T = 293 K
β = 94.663 (2)°	Block, colourless
V = 1816.41 (14) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	7768 independent reflections
Radiation source: fine-focus sealed tube	5150 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and ϕ scans	θ_max = 34.8°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→15
T_min = 0.943, T_max = 0.961	k = −28→28
29183 measured reflections	l = −15→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0779P)² + 0.2141P] where P = (F_o² + 2F_c²)/3
7768 reflections	(Δ/σ)_max = 0.002
235 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₁H₂₃NO₃S	V = 1816.41 (14) Å³
M_r = 369.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9858 (5) Å	µ = 0.20 mm⁻¹
b = 17.8830 (8) Å	T = 293 K
c = 10.2054 (4) Å	0.30 × 0.25 × 0.20 mm
β = 94.663 (2)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	7768 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	5150 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.961	R_int = 0.034
29183 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	Δρ_max = 0.38 e Å⁻³
7768 reflections	Δρ_min = −0.23 e Å⁻³
235 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.74184 (4)	1.12013 (2)	0.65807 (4)	0.0494 (1)
O1	0.57658 (8)	0.80765 (4)	0.59355 (7)	0.0381 (2)
O2	0.78980 (10)	0.74731 (5)	0.76920 (9)	0.0485 (3)
O3	0.89870 (8)	0.94723 (5)	0.64326 (9)	0.0436 (3)
N1	0.67629 (9)	0.98089 (5)	0.59254 (9)	0.0340 (2)
C1	0.50176 (11)	0.84125 (6)	0.68238 (10)	0.0325 (3)
C2	0.37387 (12)	0.81698 (7)	0.70780 (13)	0.0429 (3)
C3	0.30109 (13)	0.85474 (8)	0.79647 (15)	0.0506 (4)
C4	0.35388 (13)	0.91678 (8)	0.86141 (14)	0.0500 (4)
C5	0.48200 (12)	0.94056 (7)	0.83674 (12)	0.0398 (3)
C6	0.55823 (10)	0.90457 (6)	0.74765 (10)	0.0305 (2)
C7	0.68950 (10)	0.94036 (5)	0.71960 (9)	0.0289 (2)
C8	0.81406 (10)	0.89322 (6)	0.70168 (10)	0.0322 (3)
C9	0.88694 (10)	0.86250 (6)	0.82490 (11)	0.0337 (3)
C10	0.96886 (12)	0.90696 (7)	0.90900 (12)	0.0431 (3)
C11	1.03721 (13)	0.87723 (9)	1.02151 (14)	0.0512 (4)
C12	1.02422 (13)	0.80285 (9)	1.04927 (13)	0.0512 (4)
C13	0.94301 (13)	0.75665 (8)	0.96711 (13)	0.0465 (4)
C14	0.87363 (11)	0.78676 (6)	0.85559 (11)	0.0372 (3)
C15	0.77313 (15)	0.66932 (7)	0.78900 (14)	0.0506 (4)
C16	0.69047 (16)	0.63866 (7)	0.67137 (15)	0.0525 (4)
C17	0.54971 (14)	0.67230 (7)	0.64497 (14)	0.0476 (4)
C18	0.53496 (15)	0.73498 (7)	0.54430 (12)	0.0475 (4)
C19	0.81413 (12)	0.99003 (6)	0.55430 (11)	0.0385 (3)
C20	0.85491 (15)	1.07215 (8)	0.55857 (18)	0.0572 (5)
C21	0.61277 (12)	1.05348 (6)	0.59768 (13)	0.0427 (3)
H2	0.33710	0.77500	0.66470	0.0510*
H3	0.21570	0.83800	0.81240	0.0610*
H4	0.30480	0.94240	0.92070	0.0600*
H5	0.51810	0.98210	0.88160	0.0480*
H7	0.71300	0.97700	0.78920	0.0350*
H8	0.79150	0.85250	0.63950	0.0390*
H10	0.97830	0.95740	0.89000	0.0520*
H11	1.09130	0.90770	1.07740	0.0610*
H12	1.07030	0.78290	1.12410	0.0610*
H13	0.93510	0.70610	0.98650	0.0560*
H15A	0.72790	0.66060	0.86820	0.0610*
H15B	0.86000	0.64480	0.79860	0.0610*
H16A	0.68140	0.58510	0.68280	0.0630*
H16B	0.73940	0.64660	0.59420	0.0630*
H17A	0.48840	0.63240	0.61600	0.0570*
H17B	0.52130	0.69110	0.72750	0.0570*
H18A	0.58740	0.72240	0.47140	0.0570*
H18B	0.44150	0.73790	0.51030	0.0570*
H19	0.81950	0.97070	0.46500	0.0460*
H20A	0.84880	1.09290	0.47050	0.0690*
H20B	0.94670	1.07740	0.59640	0.0690*
H21A	0.54100	1.05200	0.65630	0.0510*
H21B	0.57490	1.06800	0.51090	0.0510*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0521 (2)	0.0315 (2)	0.0628 (2)	−0.0031 (1)	−0.0075 (2)	−0.0057 (1)
O1	0.0453 (4)	0.0319 (4)	0.0373 (4)	−0.0076 (3)	0.0047 (3)	−0.0043 (3)
O2	0.0605 (6)	0.0298 (4)	0.0528 (5)	−0.0035 (3)	−0.0103 (4)	0.0067 (3)
O3	0.0342 (4)	0.0459 (5)	0.0514 (5)	−0.0017 (3)	0.0071 (3)	0.0131 (4)
N1	0.0372 (4)	0.0292 (4)	0.0343 (4)	−0.0051 (3)	−0.0041 (3)	0.0056 (3)
C1	0.0343 (5)	0.0290 (4)	0.0336 (5)	−0.0023 (4)	−0.0007 (4)	0.0051 (4)
C2	0.0359 (5)	0.0394 (6)	0.0527 (7)	−0.0063 (4)	−0.0007 (5)	0.0065 (5)
C3	0.0338 (6)	0.0527 (7)	0.0663 (8)	0.0000 (5)	0.0097 (5)	0.0116 (6)
C4	0.0426 (6)	0.0506 (7)	0.0590 (8)	0.0076 (5)	0.0172 (5)	0.0041 (6)
C5	0.0399 (5)	0.0364 (5)	0.0435 (6)	0.0037 (4)	0.0058 (4)	−0.0010 (4)
C6	0.0309 (4)	0.0277 (4)	0.0323 (4)	0.0010 (3)	−0.0006 (3)	0.0042 (3)
C7	0.0315 (4)	0.0247 (4)	0.0299 (4)	−0.0011 (3)	−0.0016 (3)	0.0012 (3)
C8	0.0319 (4)	0.0299 (4)	0.0347 (5)	0.0002 (3)	0.0031 (3)	0.0018 (4)
C9	0.0298 (4)	0.0331 (5)	0.0380 (5)	0.0053 (4)	0.0017 (4)	0.0011 (4)
C10	0.0387 (6)	0.0412 (6)	0.0479 (6)	0.0014 (4)	−0.0049 (4)	−0.0024 (5)
C11	0.0407 (6)	0.0623 (9)	0.0484 (7)	0.0022 (5)	−0.0094 (5)	−0.0050 (6)
C12	0.0423 (6)	0.0658 (9)	0.0443 (6)	0.0132 (6)	−0.0043 (5)	0.0077 (6)
C13	0.0456 (6)	0.0459 (7)	0.0477 (6)	0.0105 (5)	0.0015 (5)	0.0108 (5)
C14	0.0360 (5)	0.0349 (5)	0.0405 (5)	0.0060 (4)	0.0016 (4)	0.0024 (4)
C15	0.0603 (8)	0.0290 (5)	0.0624 (8)	0.0007 (5)	0.0048 (6)	0.0076 (5)
C16	0.0625 (8)	0.0299 (5)	0.0666 (9)	−0.0033 (5)	0.0146 (6)	−0.0068 (5)
C17	0.0575 (7)	0.0320 (5)	0.0539 (7)	−0.0119 (5)	0.0087 (6)	−0.0045 (5)
C18	0.0639 (8)	0.0369 (6)	0.0414 (6)	−0.0127 (5)	0.0025 (5)	−0.0084 (5)
C19	0.0454 (6)	0.0340 (5)	0.0367 (5)	−0.0031 (4)	0.0075 (4)	0.0031 (4)
C20	0.0490 (7)	0.0384 (6)	0.0860 (11)	−0.0081 (5)	0.0170 (7)	0.0104 (7)
C21	0.0378 (5)	0.0338 (5)	0.0543 (7)	−0.0020 (4)	−0.0087 (5)	0.0119 (5)

Geometric parameters (Å, º) top

S1—C20	1.7968 (16)	C16—C17	1.533 (2)
S1—C21	1.8255 (12)	C17—C18	1.5196 (18)
O1—C1	1.3606 (13)	C19—C20	1.5236 (18)
O1—C18	1.4423 (15)	C2—H2	0.9300
O2—C14	1.3623 (14)	C3—H3	0.9300
O2—C15	1.4210 (15)	C4—H4	0.9300
O3—C8	1.4438 (14)	C5—H5	0.9300
O3—C19	1.4137 (14)	C7—H7	0.9800
N1—C7	1.4820 (13)	C8—H8	0.9800
N1—C19	1.4700 (15)	C10—H10	0.9300
N1—C21	1.4476 (14)	C11—H11	0.9300
C1—C2	1.3930 (16)	C12—H12	0.9300
C1—C6	1.4081 (15)	C13—H13	0.9300
C2—C3	1.3820 (19)	C15—H15A	0.9700
C3—C4	1.375 (2)	C15—H15B	0.9700
C4—C5	1.3905 (18)	C16—H16A	0.9700
C5—C6	1.3903 (16)	C16—H16B	0.9700
C6—C7	1.5070 (14)	C17—H17A	0.9700
C7—C8	1.5259 (14)	C17—H17B	0.9700
C8—C9	1.5047 (15)	C18—H18A	0.9700
C9—C10	1.3870 (16)	C18—H18B	0.9700
C9—C14	1.3990 (15)	C19—H19	0.9800
C10—C11	1.3927 (19)	C20—H20A	0.9700
C11—C12	1.368 (2)	C20—H20B	0.9700
C12—C13	1.390 (2)	C21—H21A	0.9700
C13—C14	1.3918 (17)	C21—H21B	0.9700
C15—C16	1.504 (2)

C20—S1—C21	87.50 (6)	C6—C5—H5	119.00
C1—O1—C18	118.15 (9)	N1—C7—H7	108.00
C14—O2—C15	119.29 (10)	C6—C7—H7	108.00
C8—O3—C19	106.75 (8)	C8—C7—H7	108.00
C7—N1—C19	105.55 (8)	O3—C8—H8	110.00
C7—N1—C21	114.52 (9)	C7—C8—H8	110.00
C19—N1—C21	109.41 (9)	C9—C8—H8	110.00
O1—C1—C2	123.22 (10)	C9—C10—H10	119.00
O1—C1—C6	116.73 (9)	C11—C10—H10	119.00
C2—C1—C6	120.03 (10)	C10—C11—H11	120.00
C1—C2—C3	120.57 (12)	C12—C11—H11	120.00
C2—C3—C4	120.55 (12)	C11—C12—H12	120.00
C3—C4—C5	118.80 (12)	C13—C12—H12	120.00
C4—C5—C6	122.52 (12)	C12—C13—H13	120.00
C1—C6—C5	117.53 (10)	C14—C13—H13	120.00
C1—C6—C7	124.94 (9)	O2—C15—H15A	110.00
C5—C6—C7	117.30 (9)	O2—C15—H15B	110.00
N1—C7—C6	110.92 (8)	C16—C15—H15A	110.00
N1—C7—C8	100.42 (8)	C16—C15—H15B	110.00
C6—C7—C8	121.22 (8)	H15A—C15—H15B	108.00
O3—C8—C7	100.96 (8)	C15—C16—H16A	108.00
O3—C8—C9	109.25 (8)	C15—C16—H16B	108.00
C7—C8—C9	116.43 (8)	C17—C16—H16A	108.00
C8—C9—C10	121.92 (10)	C17—C16—H16B	108.00
C8—C9—C14	119.49 (10)	H16A—C16—H16B	107.00
C10—C9—C14	118.58 (10)	C16—C17—H17A	108.00
C9—C10—C11	121.08 (12)	C16—C17—H17B	108.00
C10—C11—C12	119.57 (13)	C18—C17—H17A	108.00
C11—C12—C13	120.88 (13)	C18—C17—H17B	108.00
C12—C13—C14	119.37 (13)	H17A—C17—H17B	107.00
O2—C14—C9	114.90 (10)	O1—C18—H18A	109.00
O2—C14—C13	124.59 (11)	O1—C18—H18B	109.00
C9—C14—C13	120.51 (11)	C17—C18—H18A	109.00
O2—C15—C16	107.90 (11)	C17—C18—H18B	109.00
C15—C16—C17	115.67 (12)	H18A—C18—H18B	108.00
C16—C17—C18	116.46 (12)	O3—C19—H19	109.00
O1—C18—C17	114.82 (10)	N1—C19—H19	109.00
O3—C19—N1	107.02 (9)	C20—C19—H19	109.00
O3—C19—C20	111.05 (10)	S1—C20—H20A	110.00
N1—C19—C20	110.70 (10)	S1—C20—H20B	110.00
S1—C20—C19	107.32 (10)	C19—C20—H20A	110.00
S1—C21—N1	107.36 (8)	C19—C20—H20B	110.00
C1—C2—H2	120.00	H20A—C20—H20B	109.00
C3—C2—H2	120.00	S1—C21—H21A	110.00
C2—C3—H3	120.00	S1—C21—H21B	110.00
C4—C3—H3	120.00	N1—C21—H21A	110.00
C3—C4—H4	121.00	N1—C21—H21B	110.00
C5—C4—H4	121.00	H21A—C21—H21B	109.00
C4—C5—H5	119.00

C21—S1—C20—C19	−32.36 (10)	C4—C5—C6—C7	173.95 (11)
C20—S1—C21—N1	39.77 (9)	C4—C5—C6—C1	−0.75 (17)
C18—O1—C1—C2	−13.60 (15)	C5—C6—C7—C8	141.10 (10)
C18—O1—C1—C6	167.96 (10)	C5—C6—C7—N1	−101.65 (11)
C1—O1—C18—C17	−68.41 (14)	C1—C6—C7—C8	−44.64 (14)
C14—O2—C15—C16	−172.86 (11)	C1—C6—C7—N1	72.61 (12)
C15—O2—C14—C9	177.78 (11)	N1—C7—C8—C9	160.85 (9)
C15—O2—C14—C13	−2.20 (18)	C6—C7—C8—O3	165.12 (8)
C8—O3—C19—C20	140.90 (10)	C6—C7—C8—C9	−76.76 (12)
C8—O3—C19—N1	19.98 (11)	N1—C7—C8—O3	42.72 (9)
C19—O3—C8—C9	−162.56 (9)	C7—C8—C9—C10	−76.25 (13)
C19—O3—C8—C7	−39.33 (10)	O3—C8—C9—C14	−141.97 (10)
C21—N1—C19—C20	11.04 (14)	C7—C8—C9—C14	104.54 (11)
C19—N1—C7—C6	−160.77 (8)	O3—C8—C9—C10	37.25 (14)
C7—N1—C19—C20	−112.65 (11)	C8—C9—C14—C13	178.22 (10)
C19—N1—C21—S1	−35.51 (11)	C8—C9—C10—C11	−178.96 (11)
C21—N1—C7—C8	−151.80 (9)	C8—C9—C14—O2	−1.76 (15)
C21—N1—C19—O3	132.18 (9)	C14—C9—C10—C11	0.26 (17)
C19—N1—C7—C8	−31.39 (9)	C10—C9—C14—C13	−1.02 (17)
C7—N1—C19—O3	8.49 (10)	C10—C9—C14—O2	179.01 (10)
C21—N1—C7—C6	78.83 (11)	C9—C10—C11—C12	0.45 (19)
C7—N1—C21—S1	82.72 (10)	C10—C11—C12—C13	−0.4 (2)
C2—C1—C6—C7	−174.06 (10)	C11—C12—C13—C14	−0.3 (2)
C2—C1—C6—C5	0.19 (16)	C12—C13—C14—O2	−178.97 (12)
C6—C1—C2—C3	0.27 (18)	C12—C13—C14—C9	1.06 (18)
O1—C1—C6—C5	178.68 (10)	O2—C15—C16—C17	−60.14 (15)
O1—C1—C2—C3	−178.11 (11)	C15—C16—C17—C18	96.72 (15)
O1—C1—C6—C7	4.43 (15)	C16—C17—C18—O1	−80.88 (15)
C1—C2—C3—C4	−0.2 (2)	O3—C19—C20—S1	−100.26 (11)
C2—C3—C4—C5	−0.3 (2)	N1—C19—C20—S1	18.46 (13)
C3—C4—C5—C6	0.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.98	2.30	2.9593 (13)	123
C8—H8···O2	0.98	2.30	2.7146 (14)	104
C3—H3···Cg1ⁱ	0.93	2.99	3.8672 (14)	158
C16—H16B···Cg1ⁱⁱ	0.97	2.81	3.7400 (17)	160

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃NO₃S
M_r	369.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.9858 (5), 17.8830 (8), 10.2054 (4)
β (°)	94.663 (2)
V (Å³)	1816.41 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.943, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	29183, 7768, 5150
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.804

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.152, 1.02
No. of reflections	7768
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.23

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.98	2.30	2.9593 (13)	123
C8—H8···O2	0.98	2.30	2.7146 (14)	104
C3—H3···Cg1ⁱ	0.93	2.99	3.8672 (14)	158
C16—H16B···Cg1ⁱⁱ	0.97	2.81	3.7400 (17)	160

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

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India for data collection. SK, TS and DV the UGC (SAP–CAS) for the departmental facilities. SK thanks the DST PURSE for a Junior Research Fellowship and TS thanks the DST Inspire for a fellowship.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Guo, C. B., Guo, Y. S., Guo, Z. R., Xiao, J. F., Chu, F. M. & Cheng, G. F. (2006). Acta Chim. Sin. 64, 1559–1564. CAS Google Scholar
Karegoudar, P., Karthikeyan, M. S., Prasad, D. J., Mahalinga, M., Holla, B. S. & Kumari, N. S. (2008). Eur. J. Med. Chem. 43, 261–267. Web of Science CrossRef PubMed CAS Google Scholar
Reddy, K. A., Lohray, B. B., Bhushan, V., Bajji, A. C., Reddy, K. V., Reddy, P. R., Krishna, T. H., Rao, I. N. & Jajoo, H. K. (1999). J. Med. Chem. 42, 1927–1940. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 6| June 2013| Page o892

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

8,13,26-Trioxa-23-thia-21-aza­penta­cyclo­[18.6.0.02,7.014,19.021,25]hexa­cosa-2(7),3,5,14,16,18-hexa­ene

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

8,13,26-Trioxa-23-thia-21-azapentacyclo[18.6.0.0^2,7.0^14,19.0^21,25]hexacosa-2(7),3,5,14,16,18-hexaene