11-(p-Tolylsulfonyl)-8,14,24-trioxa-11,22,23-triazatetracyclo[19.2.1.02,7.015,20]tetracosa-1(23),2,4,6,15,17,19,21-octaene

Tian, X.; Han, J.-R.; Zhen, X.-L.; Li, Z.-C.; Liu, S.-X.

doi:10.1107/S1600536809025070

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1792

doi:10.1107/S1600536809025070

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11-(p-Tolylsulfonyl)-8,14,24-trioxa-11,22,23-triazatetracyclo[19.2.1.0^2,7.0^15,20]tetracosa-1(23),2,4,6,15,17,19,21-octaene

Xia Tian,^a Jian-Rong Han,^a ^* Xiao-Li Zhen,^a Zhen-Chao Li ^a and Shou-Xin Liu ^b ‡

^aCollege of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China, and ^bCollege of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China
^*Correspondence e-mail: Han_jianrong@126.com

(Received 22 June 2009; accepted 29 June 2009; online 8 July 2009)

In the title compound, C₂₅H₂₃N₃O₅S, the central 1,3,4-oxadiazole ring makes dihedral angles of 35.05 (7), 23.68 (7) and 82.55 (8)°, with the three benzene rings. In the crystal structure, the packing is stabilized by weak non-classical intermolecular C—H⋯O hydrogen bonds, which link the molecules into an infinite network.

Related literature

For related structures, see: Du, Hua & Jin (2001 ). For applications and synthesis of fluorescent sensors, see: Tong et al. (2000 ); Silva et al. (2000 ); Valeur & Leray (2000 ). For reference geometrical data, see: Du, Hua, Wang & Yan (2001 ).

Experimental

Crystal data

C₂₅H₂₃N₃O₅S
M_r = 477.52
Monoclinic, P 2₁ /c
a = 13.0474 (19) Å
b = 9.6809 (14) Å
c = 18.261 (3) Å
β = 97.479 (3)°
V = 2286.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 294 K
0.30 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.932, T_max = 0.964
12599 measured reflections
4656 independent reflections
2878 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.106
S = 1.01
4656 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O4ⁱ	0.97	2.52	3.424 (3)	154
C20—H20⋯O4ⁱ	0.93	2.39	3.314 (3)	173
C5—H5⋯O4ⁱⁱ	0.93	2.51	3.253 (3)	137
Symmetry codes: (i) -x, -y+2, -z; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025070/pv2175sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025070/pv2175Isup2.hkl

checkCIF report

Comment top

The development of fluorescent sensors for organic molecules is of great practical importance in chemical, biological, and pharmaceutical sciences (Silva et al., 2000; Valeur et al., 2000). Therefore, the design and synthesis of new functionalized macrocycles for selective recognition of other species is of great interest to chemists. Many functionalized macrocycles have been synthesized and employed to develop fluorescent sensors (Tong et al., 2000). 2,5-Diaryl-1,3,4-oxadizole forms chiral macrocyclic phosphoramidate receptors with phosphorus oxychloride, and their crystal structures have been reported (Du, Hua & Jin, 2001). As part of an investigation of the potential recognition properties of macrocycles, we now reported the synthesis and structure of the title compound, (I).

The molecular structure of (I) is presented in Fig. 1. The oxadizole ring (O1/C1/N1/N2/C18) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.0017 Å. It makes dihedral angles of 35.05 (7), 23.68 (7) and 82.55 (8)°, respectively, with the benzene rings (C2—C7), (C12—C17) and (C19—C24). The crystal packing is stabilized by weak non-classical intermolecular C—H···O hydrogen bonds which link the molecules into an infinite network. The bond lengths and angles in (I) are within their normal ranges (Du, Hua, Wang & Yan 2001).

Related literature top

For related structures, see: Du, Hua & Jin (2001). For general background, see: Tong et al. (2000); Silva et al. (2000); Valeur et al. (2000). For reference geometrical data, see: Du, Hua, Wang & Yan (2001).

Experimental top

2,5-Di(o-hydroxyphenyl)-1,3,4-oxadiazole (0.8 g, 3.0 mmol), K₂CO₃ (1.4 g, 10 mmol) and tri-(p-phenylsulfonyl) diethanol amine (2.3 g, 4 mmol) were added and dissolved in 50 ml of DMF and the mixture was stirred at 413 K for 20 h giving a colourless precipitate. The product was isolated, recrystallized from ethyl acetate then dried in a vacuum to give the pure compound in 65% yield. colourless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of ethyl acetate.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. Packing diagram for (I), with H bonds drawn as dashed lines; H-atoms not involved in interactions have been excluded.

11-(p-Tolylsulfonyl)-8,14,24-trioxa-11,22,23-triazatetracyclo[19.2.1.0^2,7.0^15,20]tetracosa-1(23),2,4,6,15,17,19,21-octaene top

Crystal data top

C₂₅H₂₃N₃O₅S	F(000) = 1000
M_r = 477.52	D_x = 1.387 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3043 reflections
a = 13.0474 (19) Å	θ = 2.4–24.5°
b = 9.6809 (14) Å	µ = 0.19 mm⁻¹
c = 18.261 (3) Å	T = 294 K
β = 97.479 (3)°	Prism, colourless
V = 2286.9 (6) Å³	0.30 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4656 independent reflections
Radiation source: fine-focus sealed tube	2878 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→16
T_min = 0.932, T_max = 0.964	k = −12→11
12599 measured reflections	l = −18→22

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0446P)² + 0.4604P] where P = (F_o² + 2F_c²)/3
4656 reflections	(Δ/σ)_max = 0.001
308 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₅H₂₃N₃O₅S	V = 2286.9 (6) Å³
M_r = 477.52	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.0474 (19) Å	µ = 0.19 mm⁻¹
b = 9.6809 (14) Å	T = 294 K
c = 18.261 (3) Å	0.30 × 0.22 × 0.20 mm
β = 97.479 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4656 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2878 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.964	R_int = 0.044
12599 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.01	Δρ_max = 0.20 e Å⁻³
4656 reflections	Δρ_min = −0.33 e Å⁻³
308 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
S1	0.08777 (4)	1.10726 (6)	0.12913 (3)	0.03359 (16)
N1	0.52489 (14)	0.5209 (2)	0.19897 (11)	0.0429 (5)
N2	0.56917 (14)	0.5766 (2)	0.13898 (11)	0.0433 (5)
N3	0.18176 (14)	0.99856 (19)	0.12592 (10)	0.0368 (5)
O1	0.40350 (11)	0.62864 (15)	0.12555 (8)	0.0346 (4)
O2	0.26584 (14)	0.73372 (16)	0.20414 (9)	0.0478 (5)
O3	0.35451 (12)	0.84722 (17)	0.04510 (8)	0.0452 (4)
O4	−0.00564 (11)	1.04490 (16)	0.09383 (9)	0.0417 (4)
O5	0.09239 (13)	1.15346 (17)	0.20368 (9)	0.0470 (4)
C1	0.42829 (17)	0.5545 (2)	0.18849 (12)	0.0317 (5)
C2	0.34817 (16)	0.5205 (2)	0.23424 (11)	0.0317 (5)
C3	0.35206 (18)	0.3940 (2)	0.27068 (12)	0.0397 (6)
H3	0.4059	0.3331	0.2658	0.048*
C4	0.27714 (19)	0.3576 (2)	0.31399 (13)	0.0437 (6)
H4	0.2803	0.2728	0.3381	0.052*
C5	0.19776 (19)	0.4482 (3)	0.32114 (13)	0.0443 (6)
H5	0.1467	0.4236	0.3498	0.053*
C6	0.19281 (19)	0.5752 (2)	0.28641 (13)	0.0424 (6)
H6	0.1393	0.6360	0.2924	0.051*
C7	0.26729 (18)	0.6122 (2)	0.24268 (12)	0.0354 (5)
C8	0.2383 (2)	0.8580 (2)	0.23870 (13)	0.0436 (6)
H8A	0.2783	0.8672	0.2871	0.052*
H8B	0.1656	0.8563	0.2448	0.052*
C9	0.26014 (17)	0.9778 (2)	0.19023 (12)	0.0380 (6)
H9A	0.2653	1.0614	0.2197	0.046*
H9B	0.3266	0.9629	0.1731	0.046*
C10	0.18136 (17)	0.9098 (2)	0.06069 (12)	0.0354 (5)
H10A	0.1165	0.9236	0.0291	0.042*
H10B	0.1832	0.8143	0.0769	0.042*
C11	0.26861 (17)	0.9320 (2)	0.01498 (13)	0.0393 (6)
H11A	0.2465	0.9067	−0.0360	0.047*
H11B	0.2888	1.0285	0.0165	0.047*
C12	0.42882 (17)	0.8148 (2)	0.00178 (12)	0.0351 (5)
C13	0.43787 (18)	0.8787 (3)	−0.06523 (13)	0.0429 (6)
H13	0.3909	0.9467	−0.0833	0.052*
C14	0.51633 (19)	0.8415 (3)	−0.10495 (14)	0.0473 (7)
H14	0.5211	0.8837	−0.1501	0.057*
C15	0.58800 (19)	0.7424 (3)	−0.07867 (14)	0.0470 (7)
H15	0.6413	0.7190	−0.1055	0.056*
C16	0.57964 (18)	0.6787 (2)	−0.01234 (13)	0.0413 (6)
H16	0.6278	0.6119	0.0054	0.050*
C17	0.50033 (16)	0.7125 (2)	0.02867 (12)	0.0323 (5)
C18	0.49498 (16)	0.6389 (2)	0.09783 (12)	0.0320 (5)
C19	0.11113 (16)	1.2493 (2)	0.07299 (12)	0.0329 (5)
C20	0.09314 (19)	1.2366 (2)	−0.00310 (13)	0.0418 (6)
H20	0.0687	1.1537	−0.0244	0.050*
C21	0.1115 (2)	1.3470 (3)	−0.04719 (14)	0.0483 (7)
H21	0.0993	1.3378	−0.0983	0.058*
C22	0.14769 (19)	1.4715 (2)	−0.01674 (15)	0.0450 (6)
C23	0.16432 (19)	1.4821 (2)	0.05905 (15)	0.0491 (7)
H23	0.1883	1.5651	0.0804	0.059*
C24	0.14638 (18)	1.3728 (2)	0.10435 (14)	0.0425 (6)
H24	0.1580	1.3825	0.1554	0.051*
C25	0.1681 (3)	1.5912 (3)	−0.06588 (18)	0.0734 (9)
H25A	0.1336	1.6721	−0.0511	0.110*
H25B	0.1425	1.5692	−0.1162	0.110*
H25C	0.2411	1.6082	−0.0616	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0316 (3)	0.0310 (3)	0.0389 (3)	0.0016 (2)	0.0070 (2)	−0.0041 (3)
N1	0.0330 (12)	0.0535 (13)	0.0413 (12)	0.0021 (10)	0.0018 (9)	0.0105 (10)
N2	0.0297 (11)	0.0533 (13)	0.0470 (12)	0.0021 (9)	0.0046 (9)	0.0092 (11)
N3	0.0369 (11)	0.0369 (11)	0.0345 (11)	0.0112 (9)	−0.0032 (8)	−0.0079 (9)
O1	0.0283 (8)	0.0425 (9)	0.0338 (9)	0.0033 (7)	0.0068 (7)	0.0083 (7)
O2	0.0724 (12)	0.0332 (9)	0.0422 (10)	0.0133 (8)	0.0241 (9)	0.0074 (8)
O3	0.0427 (10)	0.0574 (11)	0.0379 (9)	0.0199 (8)	0.0143 (8)	0.0123 (8)
O4	0.0284 (8)	0.0413 (9)	0.0558 (10)	−0.0063 (7)	0.0069 (7)	−0.0041 (8)
O5	0.0565 (11)	0.0475 (10)	0.0388 (10)	0.0057 (8)	0.0130 (8)	−0.0086 (8)
C1	0.0338 (13)	0.0307 (12)	0.0296 (12)	−0.0003 (10)	0.0005 (10)	0.0015 (10)
C2	0.0346 (13)	0.0328 (12)	0.0268 (12)	−0.0005 (10)	0.0011 (10)	0.0009 (10)
C3	0.0420 (14)	0.0397 (13)	0.0370 (14)	0.0039 (11)	0.0042 (11)	0.0031 (12)
C4	0.0531 (16)	0.0376 (13)	0.0414 (14)	−0.0006 (12)	0.0099 (12)	0.0082 (12)
C5	0.0472 (15)	0.0469 (15)	0.0415 (14)	−0.0025 (12)	0.0163 (12)	0.0051 (12)
C6	0.0444 (14)	0.0436 (15)	0.0415 (14)	0.0086 (11)	0.0144 (12)	0.0017 (12)
C7	0.0447 (14)	0.0359 (13)	0.0261 (12)	0.0028 (11)	0.0065 (10)	0.0017 (10)
C8	0.0556 (16)	0.0386 (14)	0.0376 (14)	0.0100 (12)	0.0100 (12)	−0.0022 (11)
C9	0.0374 (13)	0.0351 (13)	0.0394 (14)	0.0019 (10)	−0.0033 (11)	−0.0012 (11)
C10	0.0348 (13)	0.0323 (12)	0.0382 (13)	0.0060 (10)	0.0013 (10)	−0.0053 (11)
C11	0.0410 (14)	0.0378 (13)	0.0382 (13)	0.0092 (11)	0.0019 (11)	0.0056 (11)
C12	0.0318 (13)	0.0421 (14)	0.0323 (13)	0.0005 (11)	0.0079 (10)	−0.0021 (11)
C13	0.0377 (14)	0.0531 (16)	0.0382 (14)	0.0018 (12)	0.0060 (11)	0.0086 (12)
C14	0.0455 (16)	0.0631 (17)	0.0344 (14)	−0.0098 (13)	0.0097 (12)	0.0043 (13)
C15	0.0371 (14)	0.0630 (17)	0.0436 (15)	−0.0064 (13)	0.0159 (12)	−0.0067 (14)
C16	0.0343 (14)	0.0472 (15)	0.0436 (15)	0.0004 (11)	0.0098 (11)	−0.0036 (12)
C17	0.0282 (12)	0.0350 (12)	0.0339 (13)	−0.0025 (10)	0.0054 (10)	−0.0024 (10)
C18	0.0254 (12)	0.0338 (12)	0.0370 (13)	−0.0006 (10)	0.0044 (10)	−0.0028 (10)
C19	0.0266 (12)	0.0301 (12)	0.0415 (14)	0.0044 (9)	0.0022 (10)	−0.0040 (11)
C20	0.0510 (15)	0.0307 (13)	0.0437 (15)	−0.0045 (11)	0.0056 (12)	−0.0087 (12)
C21	0.0591 (17)	0.0454 (15)	0.0414 (15)	−0.0025 (13)	0.0096 (13)	−0.0019 (13)
C22	0.0445 (15)	0.0355 (14)	0.0558 (17)	0.0005 (11)	0.0093 (12)	0.0040 (13)
C23	0.0549 (17)	0.0289 (13)	0.0609 (18)	−0.0068 (12)	−0.0022 (13)	−0.0063 (13)
C24	0.0474 (15)	0.0337 (14)	0.0441 (15)	−0.0008 (11)	−0.0022 (12)	−0.0059 (12)
C25	0.094 (2)	0.0480 (17)	0.080 (2)	−0.0076 (16)	0.0186 (19)	0.0143 (16)

Geometric parameters (Å, º) top

S1—O5	1.4268 (16)	C10—C11	1.512 (3)
S1—O4	1.4355 (16)	C10—H10A	0.9700
S1—N3	1.6227 (18)	C10—H10B	0.9700
S1—C19	1.765 (2)	C11—H11A	0.9700
N1—C1	1.292 (3)	C11—H11B	0.9700
N1—N2	1.410 (2)	C12—C13	1.390 (3)
N2—C18	1.295 (3)	C12—C17	1.405 (3)
N3—C9	1.467 (3)	C13—C14	1.377 (3)
N3—C10	1.468 (3)	C13—H13	0.9300
O1—C1	1.358 (2)	C14—C15	1.381 (3)
O1—C18	1.359 (2)	C14—H14	0.9300
O2—C7	1.370 (3)	C15—C16	1.376 (3)
O2—C8	1.426 (3)	C15—H15	0.9300
O3—C12	1.365 (2)	C16—C17	1.393 (3)
O3—C11	1.439 (3)	C16—H16	0.9300
C1—C2	1.458 (3)	C17—C18	1.459 (3)
C2—C3	1.392 (3)	C19—C24	1.379 (3)
C2—C7	1.403 (3)	C19—C20	1.384 (3)
C3—C4	1.381 (3)	C20—C21	1.378 (3)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.376 (3)	C21—C22	1.384 (3)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.381 (3)	C22—C23	1.377 (3)
C5—H5	0.9300	C22—C25	1.510 (3)
C6—C7	1.383 (3)	C23—C24	1.381 (3)
C6—H6	0.9300	C23—H23	0.9300
C8—C9	1.508 (3)	C24—H24	0.9300
C8—H8A	0.9700	C25—H25A	0.9600
C8—H8B	0.9700	C25—H25B	0.9600
C9—H9A	0.9700	C25—H25C	0.9600
C9—H9B	0.9700

O5—S1—O4	119.22 (10)	H10A—C10—H10B	107.4
O5—S1—N3	107.43 (10)	O3—C11—C10	108.23 (17)
O4—S1—N3	108.21 (9)	O3—C11—H11A	110.1
O5—S1—C19	108.71 (10)	C10—C11—H11A	110.1
O4—S1—C19	105.52 (10)	O3—C11—H11B	110.1
N3—S1—C19	107.21 (10)	C10—C11—H11B	110.1
C1—N1—N2	106.20 (18)	H11A—C11—H11B	108.4
C18—N2—N1	106.15 (17)	O3—C12—C13	123.8 (2)
C9—N3—C10	119.84 (17)	O3—C12—C17	116.69 (19)
C9—N3—S1	120.75 (15)	C13—C12—C17	119.5 (2)
C10—N3—S1	119.07 (14)	C14—C13—C12	120.1 (2)
C1—O1—C18	103.30 (16)	C14—C13—H13	120.0
C7—O2—C8	118.99 (17)	C12—C13—H13	120.0
C12—O3—C11	119.08 (17)	C13—C14—C15	121.0 (2)
N1—C1—O1	112.27 (18)	C13—C14—H14	119.5
N1—C1—C2	128.1 (2)	C15—C14—H14	119.5
O1—C1—C2	119.65 (18)	C16—C15—C14	119.3 (2)
C3—C2—C7	119.0 (2)	C16—C15—H15	120.3
C3—C2—C1	119.2 (2)	C14—C15—H15	120.3
C7—C2—C1	121.7 (2)	C15—C16—C17	121.2 (2)
C4—C3—C2	120.9 (2)	C15—C16—H16	119.4
C4—C3—H3	119.5	C17—C16—H16	119.4
C2—C3—H3	119.5	C16—C17—C12	118.9 (2)
C5—C4—C3	119.3 (2)	C16—C17—C18	118.3 (2)
C5—C4—H4	120.4	C12—C17—C18	122.82 (19)
C3—C4—H4	120.4	N2—C18—O1	112.08 (19)
C4—C5—C6	121.0 (2)	N2—C18—C17	127.8 (2)
C4—C5—H5	119.5	O1—C18—C17	120.08 (19)
C6—C5—H5	119.5	C24—C19—C20	119.8 (2)
C5—C6—C7	120.1 (2)	C24—C19—S1	120.53 (18)
C5—C6—H6	120.0	C20—C19—S1	119.62 (17)
C7—C6—H6	120.0	C21—C20—C19	119.9 (2)
O2—C7—C6	123.7 (2)	C21—C20—H20	120.1
O2—C7—C2	116.57 (19)	C19—C20—H20	120.1
C6—C7—C2	119.7 (2)	C20—C21—C22	121.1 (2)
O2—C8—C9	108.12 (18)	C20—C21—H21	119.4
O2—C8—H8A	110.1	C22—C21—H21	119.4
C9—C8—H8A	110.1	C23—C22—C21	118.0 (2)
O2—C8—H8B	110.1	C23—C22—C25	121.6 (2)
C9—C8—H8B	110.1	C21—C22—C25	120.4 (2)
H8A—C8—H8B	108.4	C22—C23—C24	121.9 (2)
N3—C9—C8	114.2 (2)	C22—C23—H23	119.1
N3—C9—H9A	108.7	C24—C23—H23	119.1
C8—C9—H9A	108.7	C19—C24—C23	119.3 (2)
N3—C9—H9B	108.7	C19—C24—H24	120.4
C8—C9—H9B	108.7	C23—C24—H24	120.4
H9A—C9—H9B	107.6	C22—C25—H25A	109.5
N3—C10—C11	116.19 (19)	C22—C25—H25B	109.5
N3—C10—H10A	108.2	H25A—C25—H25B	109.5
C11—C10—H10A	108.2	C22—C25—H25C	109.5
N3—C10—H10B	108.2	H25A—C25—H25C	109.5
C11—C10—H10B	108.2	H25B—C25—H25C	109.5

C1—N1—N2—C18	0.1 (2)	C11—O3—C12—C17	−168.81 (19)
O5—S1—N3—C9	−7.8 (2)	O3—C12—C13—C14	178.8 (2)
O4—S1—N3—C9	−137.76 (17)	C17—C12—C13—C14	0.2 (3)
C19—S1—N3—C9	108.86 (18)	C12—C13—C14—C15	−1.1 (4)
O5—S1—N3—C10	165.50 (16)	C13—C14—C15—C16	1.0 (4)
O4—S1—N3—C10	35.56 (19)	C14—C15—C16—C17	−0.1 (4)
C19—S1—N3—C10	−77.82 (18)	C15—C16—C17—C12	−0.8 (3)
N2—N1—C1—O1	0.2 (2)	C15—C16—C17—C18	178.9 (2)
N2—N1—C1—C2	179.1 (2)	O3—C12—C17—C16	−178.0 (2)
C18—O1—C1—N1	−0.4 (2)	C13—C12—C17—C16	0.8 (3)
C18—O1—C1—C2	−179.42 (19)	O3—C12—C17—C18	2.3 (3)
N1—C1—C2—C3	−34.2 (3)	C13—C12—C17—C18	−178.9 (2)
O1—C1—C2—C3	144.6 (2)	N1—N2—C18—O1	−0.4 (2)
N1—C1—C2—C7	145.6 (2)	N1—N2—C18—C17	−179.5 (2)
O1—C1—C2—C7	−35.6 (3)	C1—O1—C18—N2	0.5 (2)
C7—C2—C3—C4	0.7 (3)	C1—O1—C18—C17	179.69 (19)
C1—C2—C3—C4	−179.5 (2)	C16—C17—C18—N2	23.2 (3)
C2—C3—C4—C5	−0.1 (4)	C12—C17—C18—N2	−157.1 (2)
C3—C4—C5—C6	−0.8 (4)	C16—C17—C18—O1	−155.8 (2)
C4—C5—C6—C7	1.1 (4)	C12—C17—C18—O1	23.8 (3)
C8—O2—C7—C6	41.7 (3)	O5—S1—C19—C24	10.7 (2)
C8—O2—C7—C2	−140.3 (2)	O4—S1—C19—C24	139.72 (18)
C5—C6—C7—O2	177.4 (2)	N3—S1—C19—C24	−105.10 (19)
C5—C6—C7—C2	−0.5 (3)	O5—S1—C19—C20	−168.80 (18)
C3—C2—C7—O2	−178.5 (2)	O4—S1—C19—C20	−39.8 (2)
C1—C2—C7—O2	1.7 (3)	N3—S1—C19—C20	75.4 (2)
C3—C2—C7—C6	−0.4 (3)	C24—C19—C20—C21	0.6 (3)
C1—C2—C7—C6	179.8 (2)	S1—C19—C20—C21	−179.84 (19)
C7—O2—C8—C9	170.55 (19)	C19—C20—C21—C22	−0.1 (4)
C10—N3—C9—C8	−78.4 (3)	C20—C21—C22—C23	−0.4 (4)
S1—N3—C9—C8	94.9 (2)	C20—C21—C22—C25	179.6 (2)
O2—C8—C9—N3	78.3 (2)	C21—C22—C23—C24	0.3 (4)
C9—N3—C10—C11	−70.9 (3)	C25—C22—C23—C24	−179.6 (2)
S1—N3—C10—C11	115.71 (19)	C20—C19—C24—C23	−0.7 (3)
C12—O3—C11—C10	159.53 (19)	S1—C19—C24—C23	179.78 (18)
N3—C10—C11—O3	87.7 (2)	C22—C23—C24—C19	0.2 (4)
C11—O3—C12—C13	12.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O4ⁱ	0.97	2.52	3.424 (3)	154
C20—H20···O4ⁱ	0.93	2.39	3.314 (3)	173
C5—H5···O4ⁱⁱ	0.93	2.51	3.253 (3)	137

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

Experimental details

Crystal data
Chemical formula	C₂₅H₂₃N₃O₅S
M_r	477.52
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	13.0474 (19), 9.6809 (14), 18.261 (3)
β (°)	97.479 (3)
V (Å³)	2286.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.30 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.932, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	12599, 4656, 2878
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.106, 1.01
No. of reflections	4656
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.33

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS (Sheldrick, 2008), SHELXL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O4ⁱ	0.97	2.52	3.424 (3)	154.2
C20—H20···O4ⁱ	0.93	2.39	3.314 (3)	172.8
C5—H5···O4ⁱⁱ	0.93	2.51	3.253 (3)	136.6

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

Footnotes

‡Additional contact author, e-mail: chlsx@263.net.

Acknowledgements

This work was supported by the NSFC of Hebei Province (No. B2009000670), the Foundation of the Education Department of Hebei Province and the Foundation of Hebei University of Science & Technology (No. XL200746), which are gratefully acknowledged.

References

Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Du, D. M., Hua, W. T. & Jin, X. L. (2001). J. Mol. Struct. 561, 145–152. Web of Science CSD CrossRef CAS Google Scholar
Du, D. M., Hua, W. T., Wang, Z. M. & Yan, C. H. (2001). Heteroat. Chem. 12, 480–484. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Silva, A. P. D., Fox, D. B., Huxley, A. J. M. & Moody, T. S. (2000). Coord. Chem. Rev. 205, 41–57. Google Scholar
Tong, A. J., Song, Y. S., Li, L. D., Hayashita, T., Teramae, N., Park, C. & Bartsch, R. A. (2000). Ana. Chim. Acta, 420, 57–64. Web of Science CrossRef CAS Google Scholar
Valeur, B. & Leray, I. (2000). Coord. Chem. Rev. 205, 3–40. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 8| August 2009| Page o1792

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

11-(p-Tolylsulfonyl)-8,14,24-trioxa-11,22,23-tri­aza­tetra­cyclo[19.2.1.02,7.015,20]tetracosa-1(23),2,4,6,15,17,19,21-octa­ene­

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

11-(p-Tolylsulfonyl)-8,14,24-trioxa-11,22,23-triazatetracyclo[19.2.1.0^2,7.0^15,20]tetracosa-1(23),2,4,6,15,17,19,21-octaene