8,11,24-Trioxa-21-thia-19-aza-penta-cyclo-[16.6.0.0(2,7).0(12,17).0(19,23)]tetra-cosa-2(7),3,5,12,14,16-hexa-ene.

In the title compound, C19H19NO3S, the thia-zole and oxazolidine rings each adopt an envelope conformation, with the S and O atoms as the respective flap atoms. The thia-zole and oxazolidine rings (all atoms) make a dihedral angle of 66.39 (11)° while the phenyl rings subtend a dihedral angle of 22.71 (10)°.

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

C19H19NO3S

M = 341.42

Monoclinic,

a = 10.725 (5) Å

b = 10.405 (5) Å

c = 14.930 (5) Å

β = 100.262 (5)°

V = 1639.4 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.22 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 = 0.938, T max = 0.958

15331 measured reflections

4067 independent reflections

2586 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.149

S = 1.03

4067 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.34 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/S1600536813012798/bt6902sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012798/bt6902Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012798/bt6902Isup3.cml

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

C19H19NO3S	F(000) = 720
Mr = 341.42	Dx = 1.383 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4067 reflections
a = 10.725 (5) Å	θ = 1.9–28.4°
b = 10.405 (5) Å	µ = 0.22 mm−1
c = 14.930 (5) Å	T = 293 K
β = 100.262 (5)°	Block, colourless
V = 1639.4 (12) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	4067 independent reflections
Radiation source: fine-focus sealed tube	2586 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scans	θmax = 28.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.938, Tmax = 0.958	k = −13→13
15331 measured reflections	l = −19→19

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0712P)2 + 0.3653P] where P = (Fo2 + 2Fc2)/3
4067 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.64 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.67608 (18)	0.00360 (19)	0.35262 (13)	0.0435 (4)
C2	0.5857 (2)	0.0394 (2)	0.40363 (16)	0.0580 (6)
H2	0.5126	−0.0095	0.4013	0.070*
C3	0.6040 (3)	0.1464 (3)	0.45719 (16)	0.0685 (7)
H3	0.5437	0.1692	0.4920	0.082*
C4	0.7105 (3)	0.2208 (2)	0.46029 (16)	0.0661 (7)
H4	0.7221	0.2943	0.4963	0.079*
C5	0.8005 (2)	0.1848 (2)	0.40896 (14)	0.0556 (5)
H5	0.8725	0.2352	0.4109	0.067*
C6	0.78602 (17)	0.07568 (18)	0.35488 (12)	0.0417 (4)
C7	0.88455 (17)	0.03869 (17)	0.29832 (12)	0.0386 (4)
H7	0.8874	−0.0551	0.2933	0.046*
C8	0.85966 (16)	0.09868 (18)	0.20073 (12)	0.0404 (4)
H8	0.8024	0.1723	0.1992	0.048*
C9	0.80786 (17)	0.00603 (18)	0.12575 (12)	0.0401 (4)
C10	0.8866 (2)	−0.0566 (2)	0.07553 (13)	0.0487 (5)
H10	0.9731	−0.0392	0.0872	0.058*
C11	0.8391 (2)	−0.1444 (2)	0.00832 (14)	0.0587 (6)
H11	0.8933	−0.1864	−0.0243	0.070*
C12	0.7101 (2)	−0.1691 (2)	−0.00986 (14)	0.0582 (6)
H12	0.6774	−0.2282	−0.0547	0.070*
C13	0.6300 (2)	−0.1062 (2)	0.03824 (14)	0.0517 (5)
H13	0.5434	−0.1224	0.0255	0.062*
C14	0.67837 (17)	−0.01947 (18)	0.10528 (12)	0.0404 (4)
C15	0.50032 (19)	−0.0129 (2)	0.18360 (16)	0.0538 (5)
H15A	0.4389	−0.0404	0.1314	0.065*
H15B	0.4584	0.0468	0.2184	0.065*
C16	0.54456 (18)	−0.1283 (2)	0.24204 (15)	0.0535 (5)
H16A	0.4819	−0.1488	0.2793	0.064*
H16B	0.5516	−0.2015	0.2031	0.064*
C17	1.05652 (19)	0.1675 (2)	0.27269 (14)	0.0507 (5)
H17	1.0490	0.2583	0.2885	0.061*
C18	1.1925 (2)	0.1351 (3)	0.27092 (18)	0.0690 (7)
H18A	1.2486	0.1820	0.3178	0.083*
H18B	1.2140	0.1560	0.2122	0.083*
C19	1.1041 (2)	−0.0106 (2)	0.37495 (17)	0.0653 (6)
H19A	1.0625	−0.0903	0.3861	0.078*
H19B	1.1540	0.0186	0.4320	0.078*
N1	1.01005 (14)	0.08607 (16)	0.33910 (11)	0.0472 (4)
O1	0.66449 (12)	−0.10640 (12)	0.29984 (9)	0.0473 (3)
O2	0.60208 (12)	0.05173 (13)	0.15245 (9)	0.0488 (4)
O3	0.98101 (12)	0.14160 (14)	0.18684 (9)	0.0507 (4)
S1	1.20505 (6)	−0.03571 (7)	0.29167 (6)	0.0782 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0465 (10)	0.0417 (10)	0.0441 (10)	0.0101 (8)	0.0126 (8)	0.0106 (8)
C2	0.0566 (13)	0.0594 (14)	0.0645 (13)	0.0105 (10)	0.0288 (11)	0.0127 (11)
C3	0.0815 (18)	0.0714 (16)	0.0609 (14)	0.0299 (14)	0.0351 (13)	0.0091 (12)
C4	0.0878 (18)	0.0574 (14)	0.0537 (12)	0.0204 (13)	0.0147 (12)	−0.0083 (11)
C5	0.0636 (13)	0.0524 (13)	0.0502 (11)	0.0061 (10)	0.0086 (10)	−0.0087 (10)
C6	0.0450 (10)	0.0420 (10)	0.0374 (9)	0.0067 (8)	0.0053 (8)	0.0034 (8)
C7	0.0368 (9)	0.0384 (10)	0.0402 (9)	0.0004 (7)	0.0064 (7)	−0.0012 (8)
C8	0.0376 (9)	0.0396 (10)	0.0436 (9)	−0.0009 (7)	0.0061 (7)	0.0032 (8)
C9	0.0437 (10)	0.0402 (10)	0.0353 (8)	0.0010 (8)	0.0045 (8)	0.0072 (8)
C10	0.0463 (11)	0.0575 (13)	0.0429 (10)	0.0006 (9)	0.0090 (8)	0.0003 (9)
C11	0.0670 (14)	0.0629 (14)	0.0479 (11)	0.0057 (11)	0.0153 (10)	−0.0063 (10)
C12	0.0724 (15)	0.0548 (13)	0.0444 (11)	−0.0044 (11)	0.0025 (10)	−0.0077 (10)
C13	0.0488 (11)	0.0515 (12)	0.0514 (11)	−0.0051 (9)	−0.0007 (9)	0.0001 (10)
C14	0.0410 (10)	0.0410 (10)	0.0379 (9)	0.0019 (8)	0.0036 (8)	0.0063 (8)
C15	0.0374 (10)	0.0616 (13)	0.0622 (12)	0.0019 (9)	0.0083 (9)	0.0054 (11)
C16	0.0416 (11)	0.0523 (13)	0.0676 (13)	−0.0057 (9)	0.0127 (10)	0.0010 (10)
C17	0.0539 (12)	0.0419 (11)	0.0545 (11)	−0.0115 (9)	0.0044 (9)	−0.0019 (9)
C18	0.0471 (12)	0.0852 (18)	0.0733 (15)	−0.0232 (12)	0.0072 (11)	0.0086 (14)
C19	0.0432 (11)	0.0781 (16)	0.0700 (14)	0.0011 (11)	−0.0025 (10)	0.0228 (13)
N1	0.0386 (8)	0.0540 (10)	0.0465 (9)	−0.0036 (7)	0.0012 (7)	−0.0003 (8)
O1	0.0407 (7)	0.0416 (8)	0.0598 (8)	0.0031 (6)	0.0095 (6)	0.0025 (6)
O2	0.0420 (7)	0.0461 (8)	0.0591 (8)	0.0028 (6)	0.0114 (6)	0.0029 (6)
O3	0.0468 (8)	0.0582 (9)	0.0470 (7)	−0.0132 (6)	0.0076 (6)	0.0059 (7)
S1	0.0494 (4)	0.0816 (5)	0.1040 (6)	0.0119 (3)	0.0148 (3)	−0.0004 (4)

C1—O1	1.383 (2)	C12—C13	1.378 (3)
C1—C2	1.386 (3)	C12—H12	0.9300
C1—C6	1.393 (3)	C13—C14	1.379 (3)
C2—C3	1.364 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—O2	1.386 (2)
C3—C4	1.374 (4)	C15—O2	1.428 (2)
C3—H3	0.9300	C15—C16	1.510 (3)
C4—C5	1.386 (3)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C6	1.386 (3)	C16—O1	1.434 (2)
C5—H5	0.9300	C16—H16A	0.9700
C6—C7	1.515 (3)	C16—H16B	0.9700
C7—N1	1.461 (2)	C17—O3	1.415 (2)
C7—C8	1.564 (2)	C17—N1	1.458 (3)
C7—H7	0.9800	C17—C18	1.501 (3)
C8—O3	1.426 (2)	C17—H17	0.9800
C8—C9	1.506 (3)	C18—S1	1.805 (3)
C8—H8	0.9800	C18—H18A	0.9700
C9—C10	1.388 (3)	C18—H18B	0.9700
C9—C14	1.393 (3)	C19—N1	1.457 (3)
C10—C11	1.386 (3)	C19—S1	1.808 (3)
C10—H10	0.9300	C19—H19A	0.9700
C11—C12	1.386 (3)	C19—H19B	0.9700
C11—H11	0.9300
O1—C1—C2	122.33 (19)	C12—C13—H13	120.0
O1—C1—C6	116.70 (16)	C14—C13—H13	120.0
C2—C1—C6	120.9 (2)	C13—C14—O2	122.64 (17)
C3—C2—C1	120.0 (2)	C13—C14—C9	121.01 (18)
C3—C2—H2	120.0	O2—C14—C9	116.27 (16)
C1—C2—H2	120.0	O2—C15—C16	112.49 (16)
C2—C3—C4	120.8 (2)	O2—C15—H15A	109.1
C2—C3—H3	119.6	C16—C15—H15A	109.1
C4—C3—H3	119.6	O2—C15—H15B	109.1
C3—C4—C5	119.0 (2)	C16—C15—H15B	109.1
C3—C4—H4	120.5	H15A—C15—H15B	107.8
C5—C4—H4	120.5	O1—C16—C15	112.16 (16)
C4—C5—C6	121.8 (2)	O1—C16—H16A	109.2
C4—C5—H5	119.1	C15—C16—H16A	109.2
C6—C5—H5	119.1	O1—C16—H16B	109.2
C5—C6—C1	117.49 (18)	C15—C16—H16B	109.2
C5—C6—C7	121.07 (18)	H16A—C16—H16B	107.9
C1—C6—C7	121.41 (17)	O3—C17—N1	107.18 (15)
N1—C7—C6	111.36 (15)	O3—C17—C18	110.00 (18)
N1—C7—C8	104.20 (14)	N1—C17—C18	109.38 (18)
C6—C7—C8	113.43 (14)	O3—C17—H17	110.1
N1—C7—H7	109.2	N1—C17—H17	110.1
C6—C7—H7	109.2	C18—C17—H17	110.1
C8—C7—H7	109.2	C17—C18—S1	105.17 (14)
O3—C8—C9	108.52 (14)	C17—C18—H18A	110.7
O3—C8—C7	104.59 (14)	S1—C18—H18A	110.7
C9—C8—C7	114.59 (15)	C17—C18—H18B	110.7
O3—C8—H8	109.7	S1—C18—H18B	110.7
C9—C8—H8	109.7	H18A—C18—H18B	108.8
C7—C8—H8	109.7	N1—C19—S1	107.90 (15)
C10—C9—C14	118.11 (18)	N1—C19—H19A	110.1
C10—C9—C8	121.49 (17)	S1—C19—H19A	110.1
C14—C9—C8	120.40 (16)	N1—C19—H19B	110.1
C11—C10—C9	121.33 (19)	S1—C19—H19B	110.1
C11—C10—H10	119.3	H19A—C19—H19B	108.4
C9—C10—H10	119.3	C17—N1—C19	110.68 (17)
C12—C11—C10	119.3 (2)	C17—N1—C7	108.30 (15)
C12—C11—H11	120.3	C19—N1—C7	116.49 (17)
C10—C11—H11	120.3	C1—O1—C16	117.03 (14)
C13—C12—C11	120.2 (2)	C14—O2—C15	117.95 (16)
C13—C12—H12	119.9	C17—O3—C8	108.54 (14)
C11—C12—H12	119.9	C18—S1—C19	86.56 (12)
C12—C13—C14	120.0 (2)
O1—C1—C2—C3	177.59 (19)	C10—C9—C14—C13	1.2 (3)
C6—C1—C2—C3	−0.2 (3)	C8—C9—C14—C13	−178.50 (17)
C1—C2—C3—C4	1.0 (3)	C10—C9—C14—O2	−175.54 (16)
C2—C3—C4—C5	−0.8 (4)	C8—C9—C14—O2	4.7 (2)
C3—C4—C5—C6	−0.2 (3)	O2—C15—C16—O1	37.5 (3)
C4—C5—C6—C1	1.0 (3)	O3—C17—C18—S1	−83.13 (18)
C4—C5—C6—C7	179.23 (18)	N1—C17—C18—S1	34.3 (2)
O1—C1—C6—C5	−178.67 (16)	O3—C17—N1—C19	112.63 (19)
C2—C1—C6—C5	−0.8 (3)	C18—C17—N1—C19	−6.6 (2)
O1—C1—C6—C7	3.1 (2)	O3—C17—N1—C7	−16.2 (2)
C2—C1—C6—C7	−179.04 (17)	C18—C17—N1—C7	−135.44 (18)
C5—C6—C7—N1	27.6 (2)	S1—C19—N1—C17	−24.3 (2)
C1—C6—C7—N1	−154.15 (16)	S1—C19—N1—C7	100.01 (18)
C5—C6—C7—C8	−89.5 (2)	C6—C7—N1—C17	−122.40 (17)
C1—C6—C7—C8	88.7 (2)	C8—C7—N1—C17	0.25 (19)
N1—C7—C8—O3	15.47 (18)	C6—C7—N1—C19	112.12 (19)
C6—C7—C8—O3	136.75 (16)	C8—C7—N1—C19	−125.24 (18)
N1—C7—C8—C9	134.16 (16)	C2—C1—O1—C16	47.3 (2)
C6—C7—C8—C9	−104.56 (18)	C6—C1—O1—C16	−134.80 (18)
O3—C8—C9—C10	20.6 (2)	C15—C16—O1—C1	51.5 (2)
C7—C8—C9—C10	−95.9 (2)	C13—C14—O2—C15	44.0 (2)
O3—C8—C9—C14	−159.70 (16)	C9—C14—O2—C15	−139.28 (17)
C7—C8—C9—C14	83.8 (2)	C16—C15—O2—C14	55.3 (2)
C14—C9—C10—C11	−1.5 (3)	N1—C17—O3—C8	27.1 (2)
C8—C9—C10—C11	178.18 (18)	C18—C17—O3—C8	145.91 (17)
C9—C10—C11—C12	0.8 (3)	C9—C8—O3—C17	−148.93 (15)
C10—C11—C12—C13	0.3 (3)	C7—C8—O3—C17	−26.20 (19)
C11—C12—C13—C14	−0.6 (3)	C17—C18—S1—C19	−40.58 (17)
C12—C13—C14—O2	176.39 (17)	N1—C19—S1—C18	37.84 (17)
C12—C13—C14—C9	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1	0.93	2.51	2.834 (3)	101
C7—H7···O1	0.98	2.47	2.805 (3)	100
C10—H10···O3	0.93	2.39	2.728 (3)	101