8,13,26-Trioxa-23-thia-21-aza-penta-cyclo-[18.6.0.0(2,7).0(14,19).0(21,25)]hexa-cosa-2(7),3,5,14,16,18-hexa-ene.

In the title compound, C21H23NO3S, both the thia-zole and oxazolidine rings adopt twist conformations. The mean plane of the thia-zole 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 intra-molecular C-H⋯O hydrogen bonds in the mol-ecular structure. In the crystal, mol-ecules are linked via C-H⋯π inter-actions, 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 = 369.46

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.152

S = 1.02

7768 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.23 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012804/su2596sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012804/su2596Isup3.cml

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

C21H23NO3S	F(000) = 784
Mr = 369.46	Dx = 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

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

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(Fo2) + (0.0779P)2 + 0.2141P] where P = (Fo2 + 2Fc2)/3
7768 reflections	(Δ/σ)max = 0.002
235 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .